# Electronic Supplementary Material (ESI) for Dalton Transactions. # This journal is © The Royal Society of Chemistry 2018 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_56-aldehyde _database_code_depnum_ccdc_archive 'CCDC 1532176' _audit_update_record ; 2017-12-14 deposited with the CCDC. 2018-03-06 downloaded from the CCDC. ; _audit_creation_method SHELXL-2014/7 _shelx_SHELXL_version_number 2014/7 _chemical_name_systematic (5R,7R)-6,6-dimethyl-5,6,7,8-tetrahydro-5,7-methanoquinoline-2-carbaldehyde _chemical_name_common ? _chemical_formula_moiety 'C13 H15 N O' _chemical_formula_sum 'C13 H15 N O' _exptl_crystal_recrystallization_method ethylacetate _chemical_melting_point ? _exptl_crystal_description plate _exptl_crystal_colour colourless _diffrn_ambient_temperature 200(2) _chemical_formula_weight 201.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_H-M_alt 'P 21' _space_group_name_Hall 'P 2yb' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.5369(4) _cell_length_b 7.0071(3) _cell_length_c 12.2187(7) _cell_angle_alpha 90 _cell_angle_beta 100.720(5) _cell_angle_gamma 90 _cell_volume 549.91(5) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 7550 _cell_measurement_theta_min 1.69 _cell_measurement_theta_max 25.60 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.215 _exptl_crystal_F_000 216 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.650 _exptl_crystal_size_mid 0.410 _exptl_crystal_size_min 0.200 _exptl_absorpt_coefficient_mu 0.077 _shelx_estimated_absorpt_T_min 0.952 _shelx_estimated_absorpt_T_max 0.985 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details ; STOE X-Red32, absorption correction by Gaussian integration, analogous to P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal Structure Analysis", published in F. R. Ahmed (Editor), "Crystallographic Computing", Munksgaard, Copenhagen (1970), 255 - 270 ; _exptl_absorpt_correction_T_min 0.7733 _exptl_absorpt_correction_T_max 0.9392 _exptl_absorpt_special_details ? _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'sealed X-ray tube, 12x0.4 mm long-fine focus' _diffrn_measurement_device '2-circle diffractometer' _diffrn_measurement_device_type 'STOE IPDS II' _diffrn_measurement_method 'rotation method, \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 7168 _diffrn_reflns_av_unetI/netI 0.0151 _diffrn_reflns_av_R_equivalents 0.0286 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.696 _diffrn_reflns_theta_max 25.050 _diffrn_reflns_theta_full 25.050 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.986 _diffrn_reflns_point_group_measured_fraction_full 0.986 _reflns_number_total 1944 _reflns_number_gt 1834 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.815 _reflns_Friedel_fraction_max 0.971 _reflns_Friedel_fraction_full 0.971 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ? _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0568P)^2^+0.0285P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_abs_structure_details ; Flack x determined using 789 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). The Flack parameter was meaningless, -0.7(10), and has been erased. ; _symmetry_cell_setting monoclinic _symmetry_space_group_name_h-m 'P 21' _symmetry_int_tables_number 4 _chemical_absolute_configuration syn _refine_ls_number_reflns 1944 _refine_ls_number_parameters 138 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0334 _refine_ls_R_factor_gt 0.0317 _refine_ls_wR_factor_ref 0.0891 _refine_ls_wR_factor_gt 0.0875 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.061 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4271(4) 0.5009(4) 0.38332(17) 0.0654(6) Uani 1 1 d . . . . . H1 H 0.5721 0.4755 0.3933 0.078 Uiso 1 1 calc R U . . . C2 C 0.3386(3) 0.5320(3) 0.48429(16) 0.0518(4) Uani 1 1 d . . . . . C3 C 0.1326(3) 0.5794(3) 0.47776(18) 0.0609(5) Uani 1 1 d . . . . . H3 H 0.0423 0.5913 0.4076 0.073 Uiso 1 1 calc R U . . . C4 C 0.0601(3) 0.6093(3) 0.57552(19) 0.0603(6) Uani 1 1 d . . . . . H4 H -0.0815 0.6425 0.5735 0.072 Uiso 1 1 calc R U . . . C5 C 0.1946(3) 0.5908(3) 0.67601(16) 0.0466(4) Uani 1 1 d . . . . . C6 C 0.4010(2) 0.5355(3) 0.67449(15) 0.0461(4) Uani 1 1 d . . . . . C7 C 0.1414(3) 0.6258(3) 0.78834(18) 0.0513(5) Uani 1 1 d . . . . . H7 H -0.0024 0.6738 0.7890 0.062 Uiso 1 1 calc R U . . . C8 C 0.2168(3) 0.4548(3) 0.86737(14) 0.0466(4) Uani 1 1 d . . . . . C9 C 0.4352(3) 0.5509(3) 0.88114(17) 0.0572(5) Uani 1 1 d . . . . . H9 H 0.5238 0.5395 0.9569 0.069 Uiso 1 1 calc R U . . . C10 C 0.5445(3) 0.5044(4) 0.78437(16) 0.0601(6) Uani 1 1 d . . . . . H10A H 0.6690 0.5866 0.7887 0.072 Uiso 1 1 calc R U . . . H10B H 0.5914 0.3698 0.7900 0.072 Uiso 1 1 calc R U . . . C11 C 0.3216(4) 0.7421(3) 0.8566(2) 0.0669(6) Uani 1 1 d . . . . . H11A H 0.3894 0.8315 0.8117 0.080 Uiso 1 1 calc R U . . . H11B H 0.2865 0.8058 0.9230 0.080 Uiso 1 1 calc R U . . . C12 C 0.1893(4) 0.2546(3) 0.82072(17) 0.0601(5) Uani 1 1 d . . . . . H12A H 0.2603 0.1639 0.8761 0.090 Uiso 1 1 calc R U . . . H12B H 0.2491 0.2465 0.7530 0.090 Uiso 1 1 calc R U . . . H12C H 0.0406 0.2236 0.8028 0.090 Uiso 1 1 calc R U . . . C13 C 0.1307(3) 0.4629(4) 0.97508(16) 0.0610(5) Uani 1 1 d . . . . . H13A H -0.0190 0.4360 0.9589 0.092 Uiso 1 1 calc R U . . . H13B H 0.1543 0.5903 1.0081 0.092 Uiso 1 1 calc R U . . . H13C H 0.2015 0.3675 1.0275 0.092 Uiso 1 1 calc R U . . . N1 N 0.4727(2) 0.5084(2) 0.58104(13) 0.0521(4) Uani 1 1 d . . . . . O1 O 0.3309(3) 0.5050(3) 0.28930(12) 0.0838(6) Uani 1 1 d . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0739(13) 0.0643(14) 0.0596(12) 0.0009(11) 0.0167(10) 0.0046(11) C2 0.0553(10) 0.0433(10) 0.0572(10) 0.0042(8) 0.0114(8) 0.0019(9) C3 0.0571(11) 0.0645(13) 0.0586(11) 0.0192(10) 0.0046(9) 0.0058(10) C4 0.0444(9) 0.0659(13) 0.0715(13) 0.0247(11) 0.0129(9) 0.0129(9) C5 0.0413(9) 0.0380(9) 0.0621(10) 0.0083(8) 0.0136(8) 0.0024(7) C6 0.0398(8) 0.0428(9) 0.0565(9) -0.0029(8) 0.0109(7) -0.0001(7) C7 0.0458(9) 0.0423(10) 0.0701(12) 0.0063(9) 0.0222(9) 0.0061(7) C8 0.0467(9) 0.0416(9) 0.0508(9) -0.0012(8) 0.0070(7) -0.0016(8) C9 0.0488(9) 0.0669(14) 0.0549(10) -0.0163(10) 0.0074(8) -0.0079(10) C10 0.0371(8) 0.0842(16) 0.0574(10) -0.0125(11) 0.0046(7) 0.0003(9) C11 0.0827(14) 0.0476(11) 0.0796(14) -0.0176(11) 0.0390(12) -0.0171(10) C12 0.0835(14) 0.0405(10) 0.0535(11) 0.0026(9) 0.0055(10) -0.0042(10) C13 0.0678(12) 0.0589(12) 0.0592(11) 0.0005(10) 0.0193(9) -0.0036(11) N1 0.0466(8) 0.0549(10) 0.0562(8) -0.0054(8) 0.0130(6) 0.0026(7) O1 0.1035(13) 0.0928(13) 0.0551(8) 0.0036(9) 0.0146(8) 0.0146(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.203(3) . ? C1 C2 1.473(3) . ? C1 H1 0.9500 . ? C2 N1 1.344(3) . ? C2 C3 1.375(3) . ? C3 C4 1.381(3) . ? C3 H3 0.9500 . ? C4 C5 1.377(3) . ? C4 H4 0.9500 . ? C5 C6 1.407(2) . ? C5 C7 1.498(3) . ? C6 N1 1.326(2) . ? C6 C10 1.504(2) . ? C7 C11 1.543(3) . ? C7 C8 1.560(3) . ? C7 H7 1.0000 . ? C8 C12 1.513(3) . ? C8 C13 1.526(2) . ? C8 C9 1.559(3) . ? C9 C10 1.526(3) . ? C9 C11 1.534(4) . ? C9 H9 1.0000 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 125.4(2) . . ? O1 C1 H1 117.3 . . ? C2 C1 H1 117.3 . . ? N1 C2 C3 123.51(18) . . ? N1 C2 C1 115.15(17) . . ? C3 C2 C1 121.33(18) . . ? C2 C3 C4 118.48(19) . . ? C2 C3 H3 120.8 . . ? C4 C3 H3 120.8 . . ? C5 C4 C3 119.47(17) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? C4 C5 C6 117.98(17) . . ? C4 C5 C7 125.65(16) . . ? C6 C5 C7 116.37(17) . . ? N1 C6 C5 122.96(16) . . ? N1 C6 C10 119.10(14) . . ? C5 C6 C10 117.94(16) . . ? C5 C7 C11 107.30(15) . . ? C5 C7 C8 109.93(14) . . ? C11 C7 C8 87.11(16) . . ? C5 C7 H7 116.2 . . ? C11 C7 H7 116.2 . . ? C8 C7 H7 116.2 . . ? C12 C8 C13 108.80(17) . . ? C12 C8 C9 118.90(17) . . ? C13 C8 C9 111.62(15) . . ? C12 C8 C7 118.51(16) . . ? C13 C8 C7 112.38(15) . . ? C9 C8 C7 85.01(15) . . ? C10 C9 C11 108.30(19) . . ? C10 C9 C8 112.07(16) . . ? C11 C9 C8 87.45(15) . . ? C10 C9 H9 115.3 . . ? C11 C9 H9 115.3 . . ? C8 C9 H9 115.3 . . ? C6 C10 C9 110.89(15) . . ? C6 C10 H10A 109.5 . . ? C9 C10 H10A 109.5 . . ? C6 C10 H10B 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 108.0 . . ? C9 C11 C7 86.42(16) . . ? C9 C11 H11A 114.2 . . ? C7 C11 H11A 114.2 . . ? C9 C11 H11B 114.2 . . ? C7 C11 H11B 114.3 . . ? H11A C11 H11B 111.4 . . ? C8 C12 H12A 109.5 . . ? C8 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C8 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C8 C13 H13A 109.5 . . ? C8 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C8 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C6 N1 C2 117.55(15) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 N1 175.8(2) . . . . ? O1 C1 C2 C3 -3.4(4) . . . . ? N1 C2 C3 C4 1.7(3) . . . . ? C1 C2 C3 C4 -179.1(2) . . . . ? C2 C3 C4 C5 -0.1(3) . . . . ? C3 C4 C5 C6 -2.0(3) . . . . ? C3 C4 C5 C7 177.53(19) . . . . ? C4 C5 C6 N1 2.8(3) . . . . ? C7 C5 C6 N1 -176.75(17) . . . . ? C4 C5 C6 C10 -176.6(2) . . . . ? C7 C5 C6 C10 3.8(2) . . . . ? C4 C5 C7 C11 -135.7(2) . . . . ? C6 C5 C7 C11 43.8(2) . . . . ? C4 C5 C7 C8 131.1(2) . . . . ? C6 C5 C7 C8 -49.4(2) . . . . ? C5 C7 C8 C12 -40.5(2) . . . . ? C11 C7 C8 C12 -147.82(19) . . . . ? C5 C7 C8 C13 -168.80(15) . . . . ? C11 C7 C8 C13 83.83(17) . . . . ? C5 C7 C8 C9 79.85(17) . . . . ? C11 C7 C8 C9 -27.51(14) . . . . ? C12 C8 C9 C10 38.9(3) . . . . ? C13 C8 C9 C10 166.82(18) . . . . ? C7 C8 C9 C10 -81.06(19) . . . . ? C12 C8 C9 C11 147.62(18) . . . . ? C13 C8 C9 C11 -84.44(18) . . . . ? C7 C8 C9 C11 27.68(14) . . . . ? N1 C6 C10 C9 177.63(18) . . . . ? C5 C6 C10 C9 -2.9(3) . . . . ? C11 C9 C10 C6 -46.4(2) . . . . ? C8 C9 C10 C6 48.4(3) . . . . ? C10 C9 C11 C7 84.48(17) . . . . ? C8 C9 C11 C7 -27.94(13) . . . . ? C5 C7 C11 C9 -82.05(17) . . . . ? C8 C7 C11 C9 27.94(14) . . . . ? C5 C6 N1 C2 -1.3(3) . . . . ? C10 C6 N1 C2 178.10(18) . . . . ? C3 C2 N1 C6 -1.0(3) . . . . ? C1 C2 N1 C6 179.74(17) . . . . ? _refine_diff_density_max 0.112 _refine_diff_density_min -0.130 _refine_diff_density_rms 0.038 _shelx_res_file ; shelx.res created by SHELXL-2014/7 TITL 5,6-Aldehyde in P2(1) CELL 0.71073 6.5369 7.0071 12.2187 90.000 100.720 90.000 ZERR 2.00 0.0004 0.0003 0.0007 0.000 0.005 0.000 LATT -1 SYMM - X, 1/2 + Y, - Z SFAC C H N O UNIT 26 30 2 2 MERG 2 OMIT -1 8 4 OMIT 2 0 7 OMIT -3 0 11 FMAP 2 PLAN 5 SIZE 0.200 0.410 0.650 ACTA BOND $H CONF LIST 6 L.S. 99 TEMP -73.00 WGHT 0.056800 0.028500 FVAR 1.47571 C1 1 0.427083 0.500922 0.383317 11.00000 0.07387 0.06427 = 0.05962 0.00087 0.01674 0.00464 AFIX 43 H1 2 0.572123 0.475528 0.393252 11.00000 -1.20000 AFIX 0 C2 1 0.338618 0.532006 0.484292 11.00000 0.05528 0.04331 = 0.05724 0.00416 0.01140 0.00185 C3 1 0.132636 0.579396 0.477761 11.00000 0.05706 0.06453 = 0.05863 0.01915 0.00463 0.00583 AFIX 43 H3 2 0.042269 0.591275 0.407595 11.00000 -1.20000 AFIX 0 C4 1 0.060101 0.609335 0.575517 11.00000 0.04442 0.06587 = 0.07146 0.02468 0.01292 0.01293 AFIX 43 H4 2 -0.081479 0.642479 0.573471 11.00000 -1.20000 AFIX 0 C5 1 0.194639 0.590764 0.676012 11.00000 0.04128 0.03800 = 0.06211 0.00829 0.01365 0.00239 C6 1 0.401007 0.535479 0.674493 11.00000 0.03978 0.04278 = 0.05650 -0.00289 0.01093 -0.00013 C7 1 0.141380 0.625795 0.788340 11.00000 0.04583 0.04229 = 0.07015 0.00629 0.02222 0.00612 AFIX 13 H7 2 -0.002439 0.673780 0.789048 11.00000 -1.20000 AFIX 0 C8 1 0.216788 0.454840 0.867367 11.00000 0.04670 0.04156 = 0.05082 -0.00116 0.00696 -0.00160 C9 1 0.435238 0.550872 0.881138 11.00000 0.04881 0.06688 = 0.05493 -0.01625 0.00740 -0.00794 AFIX 13 H9 2 0.523840 0.539504 0.956936 11.00000 -1.20000 AFIX 0 C10 1 0.544529 0.504412 0.784374 11.00000 0.03707 0.08419 = 0.05738 -0.01250 0.00463 0.00032 AFIX 23 H10A 2 0.668959 0.586599 0.788678 11.00000 -1.20000 H10B 2 0.591393 0.369825 0.789968 11.00000 -1.20000 AFIX 0 C11 1 0.321616 0.742115 0.856570 11.00000 0.08271 0.04757 = 0.07957 -0.01756 0.03904 -0.01707 AFIX 23 H11A 2 0.389448 0.831540 0.811711 11.00000 -1.20000 H11B 2 0.286493 0.805776 0.923011 11.00000 -1.20000 AFIX 0 C12 1 0.189279 0.254584 0.820716 11.00000 0.08350 0.04053 = 0.05353 0.00261 0.00553 -0.00424 AFIX 137 H12A 2 0.260325 0.163913 0.876101 11.00000 -1.50000 H12B 2 0.249072 0.246532 0.753021 11.00000 -1.50000 H12C 2 0.040615 0.223567 0.802802 11.00000 -1.50000 AFIX 0 C13 1 0.130673 0.462880 0.975079 11.00000 0.06785 0.05890 = 0.05918 0.00054 0.01925 -0.00363 AFIX 137 H13A 2 -0.019034 0.435958 0.958868 11.00000 -1.50000 H13B 2 0.154262 0.590310 1.008065 11.00000 -1.50000 H13C 2 0.201476 0.367535 1.027491 11.00000 -1.50000 AFIX 0 N1 3 0.472695 0.508417 0.581039 11.00000 0.04663 0.05490 = 0.05622 -0.00540 0.01304 0.00263 O1 4 0.330851 0.505034 0.289301 11.00000 0.10346 0.09277 = 0.05507 0.00361 0.01460 0.01465 HKLF 4 REM 5,6-Aldehyde in P2(1) REM R1 = 0.0317 for 1834 Fo > 4sig(Fo) and 0.0334 for all 1944 data REM 138 parameters refined using 1 restraints END WGHT 0.0579 0.0273 REM Highest difference peak 0.112, deepest hole -0.130, 1-sigma level 0.038 Q1 1 0.1668 0.8199 0.8970 11.00000 0.05 0.11 Q2 1 0.2129 0.7436 0.8135 11.00000 0.05 0.10 Q3 1 -0.0914 0.7694 0.3771 11.00000 0.05 0.10 Q4 1 0.7674 0.8006 0.7826 11.00000 0.05 0.09 Q5 1 0.3654 0.3032 1.1092 11.00000 0.05 0.09 ; _shelx_res_checksum 60818 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_ATE69 _database_code_depnum_ccdc_archive 'CCDC 1532178' _audit_update_record ; 2017-12-14 deposited with the CCDC. 2018-03-06 downloaded from the CCDC. ; _audit_creation_method SHELXL-2014/7 _shelx_SHELXL_version_number 2014/7 _chemical_name_systematic 6-(7,7-dimethyl-5,6,7,8-tetrahydro-6,8-methanoisoquinolin-3-yl)-2,4-diisopropyl-1,2,4,5-tetrazinan-3-one _chemical_name_common ? _chemical_formula_moiety 'C20 H31 N5 O' _chemical_formula_sum 'C20 H31 N5 O' _exptl_crystal_recrystallization_method diethylether _chemical_melting_point ? _exptl_crystal_description rectangle _exptl_crystal_colour Yellow _diffrn_ambient_temperature 200(2) _chemical_formula_weight 357.50 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_H-M_alt 'P 21 21 21' _space_group_name_Hall 'P 2ac 2ab' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 10.2955(5) _cell_length_b 12.3540(10) _cell_length_c 16.2973(9) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2072.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 5813 _cell_measurement_theta_min 2.07 _cell_measurement_theta_max 24.49 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.146 _exptl_crystal_F_000 776 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.210 _exptl_crystal_size_mid 0.120 _exptl_crystal_size_min 0.070 _exptl_absorpt_coefficient_mu 0.073 _shelx_estimated_absorpt_T_min 0.985 _shelx_estimated_absorpt_T_max 0.995 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details ; STOE X-Red32, absorption correction by Gaussian integration, analogous to P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal Structure Analysis", published in F. R. Ahmed (Editor), "Crystallographic Computing", Munksgaard, Copenhagen (1970), 255 - 270 ; _exptl_absorpt_correction_T_min 0.7757 _exptl_absorpt_correction_T_max 0.9760 _exptl_absorpt_special_details ? _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'sealed X-ray tube, 12x0.4 mm long-fine focus' _diffrn_measurement_device '2-circle diffractometer' _diffrn_measurement_device_type 'STOE IPDS II' _diffrn_measurement_method 'rotation method, \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 19064 _diffrn_reflns_av_unetI/netI 0.0735 _diffrn_reflns_av_R_equivalents 0.1324 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.069 _diffrn_reflns_theta_max 25.216 _diffrn_reflns_theta_full 25.216 _diffrn_measured_fraction_theta_max 0.989 _diffrn_measured_fraction_theta_full 0.990 _diffrn_reflns_Laue_measured_fraction_max 0.989 _diffrn_reflns_Laue_measured_fraction_full 0.990 _diffrn_reflns_point_group_measured_fraction_max 0.985 _diffrn_reflns_point_group_measured_fraction_full 0.985 _reflns_number_total 3694 _reflns_number_gt 1860 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.741 _reflns_Friedel_fraction_max 0.978 _reflns_Friedel_fraction_full 0.979 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ? _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0792P)^2^+0.6082P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method 'SHELXL-2014/7 (Sheldrick 2014' _refine_ls_extinction_coef 0.006(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details ; Flack x determined using 570 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 1.1(10) _symmetry_cell_setting ? _symmetry_space_group_name_h-m ? _symmetry_int_tables_number ? _chemical_absolute_configuration syn _refine_ls_number_reflns 3694 _refine_ls_number_parameters 236 _refine_ls_number_restraints 33 _refine_ls_R_factor_all 0.1506 _refine_ls_R_factor_gt 0.0673 _refine_ls_wR_factor_ref 0.1939 _refine_ls_wR_factor_gt 0.1530 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.013 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.8495(5) 0.7358(6) 0.3580(4) 0.0615(17) Uani 1 1 d . . . . . H1 H 0.8170 0.7378 0.4144 0.074 Uiso 1 1 calc R U . . . C2 C 0.7350(5) 0.7432(5) 0.3005(3) 0.0571(17) Uani 1 1 d . . . . . C3 C 0.6119(5) 0.7627(7) 0.3281(3) 0.076(2) Uani 1 1 d . . . . . H3 H 0.5955 0.7684 0.3841 0.092 Uiso 1 1 calc R U . . . C4 C 0.5118(5) 0.7740(7) 0.2722(3) 0.073(2) Uani 1 1 d . . . . . C5 C 0.5398(5) 0.7627(6) 0.1891(3) 0.0587(17) Uani 1 1 d . U . . . C6 C 0.6657(5) 0.7401(6) 0.1679(3) 0.0671(19) Uani 1 1 d . U . . . H6 H 0.6840 0.7308 0.1124 0.081 Uiso 1 1 calc R U . . . C7 C 0.4300(6) 0.7790(7) 0.1307(3) 0.0712(19) Uani 1 1 d . . . . . H7 H 0.4516 0.7748 0.0722 0.085 Uiso 1 1 calc R U . . . C8 C 0.3083(6) 0.7127(8) 0.1591(4) 0.081(2) Uani 1 1 d . U . . . C9 C 0.2873(7) 0.8081(7) 0.2196(4) 0.0921(16) Uani 1 1 d . U . . . H9 H 0.1963 0.8268 0.2302 0.111 Uiso 1 1 calc R U . . . C10 C 0.3715(6) 0.7950(8) 0.2963(4) 0.0921(16) Uani 1 1 d . U . . . H10A H 0.3665 0.8601 0.3293 0.111 Uiso 1 1 calc R U . . . H10B H 0.3394 0.7350 0.3289 0.111 Uiso 1 1 calc R U . . . C11 C 0.3566(7) 0.8813(8) 0.1587(5) 0.0921(16) Uani 1 1 d . U . . . H11A H 0.4114 0.9360 0.1838 0.111 Uiso 1 1 calc R U . . . H11B H 0.3004 0.9124 0.1172 0.111 Uiso 1 1 calc R U . . . C12 C 0.3284(8) 0.6000(8) 0.1923(6) 0.115(3) Uani 1 1 d . . . . . H12A H 0.2478 0.5729 0.2137 0.173 Uiso 1 1 calc R U . . . H12B H 0.3920 0.6018 0.2353 0.173 Uiso 1 1 calc R U . . . H12C H 0.3580 0.5534 0.1490 0.173 Uiso 1 1 calc R U . . . C13 C 0.2034(7) 0.7121(8) 0.0914(5) 0.105(3) Uani 1 1 d . . . . . H13A H 0.2289 0.6635 0.0484 0.157 Uiso 1 1 calc R U . . . H13B H 0.1939 0.7838 0.0695 0.157 Uiso 1 1 calc R U . . . H13C H 0.1222 0.6887 0.1143 0.157 Uiso 1 1 calc R U . . . C14 C 1.0887(5) 0.7261(7) 0.4219(4) 0.0621(16) Uani 1 1 d . . . . . C15 C 1.0716(7) 0.9226(6) 0.4401(4) 0.073(2) Uani 1 1 d . . . . . H15 H 1.1504 0.9102 0.4725 0.087 Uiso 1 1 calc R U . . . C15A C 1.0597(7) 0.5307(6) 0.4321(4) 0.071(2) Uani 1 1 d . . . . . H15A H 1.1447 0.5349 0.4591 0.085 Uiso 1 1 calc R U . . . C16 C 1.0988(8) 1.0146(6) 0.3827(5) 0.095(3) Uani 1 1 d . . . . . H16A H 1.1796 1.0019 0.3548 0.143 Uiso 1 1 calc R U . . . H16B H 1.1044 1.0808 0.4132 0.143 Uiso 1 1 calc R U . . . H16C H 1.0300 1.0199 0.3432 0.143 Uiso 1 1 calc R U . . . C16A C 1.0640(9) 0.4388(7) 0.3714(5) 0.101(3) Uani 1 1 d . . . . . H16D H 0.9832 0.4354 0.3422 0.152 Uiso 1 1 calc R U . . . H16E H 1.0780 0.3719 0.4001 0.152 Uiso 1 1 calc R U . . . H16F H 1.1337 0.4505 0.3333 0.152 Uiso 1 1 calc R U . . . C17 C 0.9610(8) 0.9451(7) 0.5001(4) 0.099(3) Uani 1 1 d . . . . . H17A H 0.8803 0.9481 0.4708 0.149 Uiso 1 1 calc R U . . . H17B H 0.9759 1.0131 0.5271 0.149 Uiso 1 1 calc R U . . . H17C H 0.9573 0.8883 0.5403 0.149 Uiso 1 1 calc R U . . . C17A C 0.9580(8) 0.5088(7) 0.4978(4) 0.097(3) Uani 1 1 d . . . . . H17D H 0.9602 0.5657 0.5379 0.145 Uiso 1 1 calc R U . . . H17E H 0.9762 0.4408 0.5240 0.145 Uiso 1 1 calc R U . . . H17F H 0.8735 0.5061 0.4730 0.145 Uiso 1 1 calc R U . . . N1 N 0.7644(4) 0.7304(5) 0.2210(3) 0.0646(14) Uani 1 1 d . . . . . N2 N 0.9157(5) 0.6345(5) 0.3456(4) 0.0698(16) Uani 1 1 d D . . . . N3 N 1.0367(5) 0.6339(5) 0.3900(3) 0.0658(15) Uani 1 1 d . . . . . N4 N 1.0467(5) 0.8242(5) 0.3924(3) 0.0672(16) Uani 1 1 d . . . . . N5 N 0.9301(6) 0.8298(5) 0.3450(4) 0.0721(17) Uani 1 1 d D . . . . O1 O 1.1769(4) 0.7209(4) 0.4733(2) 0.0690(12) Uani 1 1 d . . . . . H2N H 0.938(7) 0.630(6) 0.292(2) 0.083 Uiso 1 1 d D U . . . H5N H 0.945(6) 0.828(5) 0.2905(18) 0.083 Uiso 1 1 d D U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.036(3) 0.083(5) 0.065(4) -0.001(4) 0.002(3) 0.001(4) C2 0.043(3) 0.073(5) 0.056(3) 0.001(3) -0.005(2) 0.001(3) C3 0.052(3) 0.124(7) 0.054(3) -0.008(4) 0.000(3) 0.012(4) C4 0.045(3) 0.119(6) 0.056(3) -0.003(4) -0.002(3) 0.008(4) C5 0.048(3) 0.075(5) 0.053(3) 0.003(3) -0.003(3) 0.002(4) C6 0.050(3) 0.101(6) 0.050(3) -0.004(4) 0.000(3) 0.000(4) C7 0.053(3) 0.103(5) 0.057(3) 0.000(4) -0.005(3) 0.000(4) C8 0.050(4) 0.117(6) 0.077(4) 0.006(5) -0.015(3) -0.012(4) C9 0.053(2) 0.148(5) 0.076(3) -0.006(3) -0.012(2) 0.017(3) C10 0.053(2) 0.148(5) 0.076(3) -0.006(3) -0.012(2) 0.017(3) C11 0.053(2) 0.148(5) 0.076(3) -0.006(3) -0.012(2) 0.017(3) C12 0.084(6) 0.126(9) 0.135(8) 0.040(6) -0.012(6) -0.036(6) C13 0.066(4) 0.146(8) 0.103(5) -0.003(6) -0.024(4) -0.014(5) C14 0.042(3) 0.084(5) 0.060(3) -0.003(4) -0.007(3) -0.004(4) C15 0.064(5) 0.074(5) 0.080(5) -0.009(4) -0.018(4) -0.010(4) C15A 0.065(5) 0.073(5) 0.076(5) -0.001(4) -0.013(4) 0.006(4) C16 0.077(5) 0.078(6) 0.130(7) 0.009(5) 0.012(5) -0.011(5) C16A 0.099(7) 0.095(7) 0.109(7) -0.020(5) 0.006(5) 0.009(5) C17 0.104(6) 0.103(7) 0.091(6) -0.017(5) 0.018(5) -0.007(5) C17A 0.115(7) 0.109(7) 0.067(5) 0.008(4) -0.005(5) -0.002(5) N1 0.043(3) 0.094(4) 0.057(3) -0.002(3) 0.000(2) 0.000(3) N2 0.049(3) 0.084(4) 0.075(4) -0.009(3) -0.020(3) 0.006(3) N3 0.055(3) 0.073(4) 0.069(4) 0.002(3) -0.016(3) 0.009(3) N4 0.054(3) 0.075(4) 0.072(4) 0.002(3) -0.016(3) -0.001(3) N5 0.057(3) 0.091(5) 0.069(4) 0.008(3) -0.015(3) 0.001(3) O1 0.051(2) 0.092(3) 0.065(2) -0.001(3) -0.012(2) -0.002(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N2 1.440(9) . ? C1 N5 1.442(8) . ? C1 C2 1.509(7) . ? C1 H1 0.9800 . ? C2 N1 1.340(7) . ? C2 C3 1.366(7) . ? C3 C4 1.383(8) . ? C3 H3 0.9300 . ? C4 C5 1.391(7) . ? C4 C10 1.519(8) . ? C5 C6 1.371(7) . ? C5 C7 1.491(7) . ? C6 N1 1.341(7) . ? C6 H6 0.9300 . ? C7 C11 1.542(11) . ? C7 C8 1.566(9) . ? C7 H7 0.9800 . ? C8 C12 1.509(12) . ? C8 C13 1.543(9) . ? C8 C9 1.552(11) . ? C9 C11 1.521(11) . ? C9 C10 1.529(9) . ? C9 H9 0.9800 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 O1 1.238(6) . ? C14 N3 1.362(9) . ? C14 N4 1.373(8) . ? C15 N4 1.466(8) . ? C15 C16 1.498(10) . ? C15 C17 1.526(10) . ? C15 H15 0.9800 . ? C15A N3 1.467(9) . ? C15A C16A 1.506(10) . ? C15A C17A 1.521(10) . ? C15A H15A 0.9800 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C16A H16D 0.9600 . ? C16A H16E 0.9600 . ? C16A H16F 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C17A H17D 0.9600 . ? C17A H17E 0.9600 . ? C17A H17F 0.9600 . ? N2 N3 1.440(7) . ? N2 H2N 0.91(3) . ? N4 N5 1.430(7) . ? N5 H5N 0.90(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 C1 N5 114.0(5) . . ? N2 C1 C2 109.6(5) . . ? N5 C1 C2 108.0(5) . . ? N2 C1 H1 108.3 . . ? N5 C1 H1 108.3 . . ? C2 C1 H1 108.3 . . ? N1 C2 C3 123.3(5) . . ? N1 C2 C1 114.6(5) . . ? C3 C2 C1 122.1(5) . . ? C2 C3 C4 119.5(5) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C3 C4 C5 118.5(5) . . ? C3 C4 C10 123.7(5) . . ? C5 C4 C10 117.7(5) . . ? C6 C5 C4 117.5(5) . . ? C6 C5 C7 125.7(5) . . ? C4 C5 C7 116.8(5) . . ? N1 C6 C5 124.9(5) . . ? N1 C6 H6 117.5 . . ? C5 C6 H6 117.5 . . ? C5 C7 C11 107.0(6) . . ? C5 C7 C8 110.3(5) . . ? C11 C7 C8 87.1(6) . . ? C5 C7 H7 116.2 . . ? C11 C7 H7 116.2 . . ? C8 C7 H7 116.2 . . ? C12 C8 C13 110.4(8) . . ? C12 C8 C9 119.4(7) . . ? C13 C8 C9 111.1(7) . . ? C12 C8 C7 118.6(6) . . ? C13 C8 C7 110.6(6) . . ? C9 C8 C7 84.4(6) . . ? C11 C9 C10 109.3(6) . . ? C11 C9 C8 88.3(6) . . ? C10 C9 C8 111.1(6) . . ? C11 C9 H9 115.1 . . ? C10 C9 H9 115.1 . . ? C8 C9 H9 115.1 . . ? C4 C10 C9 110.3(5) . . ? C4 C10 H10A 109.6 . . ? C9 C10 H10A 109.6 . . ? C4 C10 H10B 109.6 . . ? C9 C10 H10B 109.6 . . ? H10A C10 H10B 108.1 . . ? C9 C11 C7 86.3(7) . . ? C9 C11 H11A 114.3 . . ? C7 C11 H11A 114.3 . . ? C9 C11 H11B 114.3 . . ? C7 C11 H11B 114.3 . . ? H11A C11 H11B 111.4 . . ? C8 C12 H12A 109.5 . . ? C8 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C8 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C8 C13 H13A 109.5 . . ? C8 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C8 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O1 C14 N3 120.2(7) . . ? O1 C14 N4 120.9(7) . . ? N3 C14 N4 118.8(5) . . ? N4 C15 C16 109.3(6) . . ? N4 C15 C17 111.1(6) . . ? C16 C15 C17 113.7(7) . . ? N4 C15 H15 107.5 . . ? C16 C15 H15 107.5 . . ? C17 C15 H15 107.5 . . ? N3 C15A C16A 110.6(6) . . ? N3 C15A C17A 111.9(6) . . ? C16A C15A C17A 110.4(7) . . ? N3 C15A H15A 107.9 . . ? C16A C15A H15A 107.9 . . ? C17A C15A H15A 107.9 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15A C16A H16D 109.5 . . ? C15A C16A H16E 109.5 . . ? H16D C16A H16E 109.5 . . ? C15A C16A H16F 109.5 . . ? H16D C16A H16F 109.5 . . ? H16E C16A H16F 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C15A C17A H17D 109.5 . . ? C15A C17A H17E 109.5 . . ? H17D C17A H17E 109.5 . . ? C15A C17A H17F 109.5 . . ? H17D C17A H17F 109.5 . . ? H17E C17A H17F 109.5 . . ? C2 N1 C6 116.2(4) . . ? C1 N2 N3 110.1(5) . . ? C1 N2 H2N 108(5) . . ? N3 N2 H2N 105(5) . . ? C14 N3 N2 121.8(5) . . ? C14 N3 C15A 119.0(6) . . ? N2 N3 C15A 112.3(6) . . ? C14 N4 N5 119.7(5) . . ? C14 N4 C15 119.4(5) . . ? N5 N4 C15 113.2(6) . . ? N4 N5 C1 111.4(5) . . ? N4 N5 H5N 113(4) . . ? C1 N5 H5N 103(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 C1 C2 N1 -55.5(8) . . . . ? N5 C1 C2 N1 69.3(8) . . . . ? N2 C1 C2 C3 125.2(7) . . . . ? N5 C1 C2 C3 -110.0(8) . . . . ? N1 C2 C3 C4 -2.4(13) . . . . ? C1 C2 C3 C4 176.8(7) . . . . ? C2 C3 C4 C5 1.3(12) . . . . ? C2 C3 C4 C10 179.5(8) . . . . ? C3 C4 C5 C6 0.5(11) . . . . ? C10 C4 C5 C6 -177.8(8) . . . . ? C3 C4 C5 C7 -178.1(8) . . . . ? C10 C4 C5 C7 3.6(11) . . . . ? C4 C5 C6 N1 -1.6(12) . . . . ? C7 C5 C6 N1 177.0(7) . . . . ? C6 C5 C7 C11 -133.5(8) . . . . ? C4 C5 C7 C11 45.0(9) . . . . ? C6 C5 C7 C8 133.2(7) . . . . ? C4 C5 C7 C8 -48.2(10) . . . . ? C5 C7 C8 C12 -40.8(9) . . . . ? C11 C7 C8 C12 -147.8(7) . . . . ? C5 C7 C8 C13 -169.7(7) . . . . ? C11 C7 C8 C13 83.3(7) . . . . ? C5 C7 C8 C9 79.8(7) . . . . ? C11 C7 C8 C9 -27.2(5) . . . . ? C12 C8 C9 C11 147.4(6) . . . . ? C13 C8 C9 C11 -82.3(7) . . . . ? C7 C8 C9 C11 27.6(5) . . . . ? C12 C8 C9 C10 37.4(9) . . . . ? C13 C8 C9 C10 167.6(6) . . . . ? C7 C8 C9 C10 -82.5(7) . . . . ? C3 C4 C10 C9 177.5(8) . . . . ? C5 C4 C10 C9 -4.3(12) . . . . ? C11 C9 C10 C4 -44.8(10) . . . . ? C8 C9 C10 C4 51.0(10) . . . . ? C10 C9 C11 C7 83.8(7) . . . . ? C8 C9 C11 C7 -28.0(5) . . . . ? C5 C7 C11 C9 -82.6(6) . . . . ? C8 C7 C11 C9 27.8(5) . . . . ? C3 C2 N1 C6 1.4(11) . . . . ? C1 C2 N1 C6 -177.8(6) . . . . ? C5 C6 N1 C2 0.6(11) . . . . ? N5 C1 N2 N3 49.3(6) . . . . ? C2 C1 N2 N3 170.5(5) . . . . ? O1 C14 N3 N2 165.1(5) . . . . ? N4 C14 N3 N2 -18.7(8) . . . . ? O1 C14 N3 C15A 16.5(8) . . . . ? N4 C14 N3 C15A -167.3(6) . . . . ? C1 N2 N3 C14 -13.4(8) . . . . ? C1 N2 N3 C15A 137.1(6) . . . . ? C16A C15A N3 C14 -148.6(6) . . . . ? C17A C15A N3 C14 87.9(7) . . . . ? C16A C15A N3 N2 60.0(8) . . . . ? C17A C15A N3 N2 -63.6(7) . . . . ? O1 C14 N4 N5 -168.6(5) . . . . ? N3 C14 N4 N5 15.2(8) . . . . ? O1 C14 N4 C15 -21.2(9) . . . . ? N3 C14 N4 C15 162.6(6) . . . . ? C16 C15 N4 C14 144.2(6) . . . . ? C17 C15 N4 C14 -89.6(8) . . . . ? C16 C15 N4 N5 -66.4(8) . . . . ? C17 C15 N4 N5 59.9(8) . . . . ? C14 N4 N5 C1 19.6(8) . . . . ? C15 N4 N5 C1 -129.7(6) . . . . ? N2 C1 N5 N4 -52.9(7) . . . . ? C2 C1 N5 N4 -175.1(5) . . . . ? _refine_diff_density_max 0.189 _refine_diff_density_min -0.188 _refine_diff_density_rms 0.037 _shelx_res_file ; shelx.res created by SHELXL-2014/7 TITL ATE69 in P2(1)2(1)2(1) CELL 0.71073 10.2955 12.3540 16.2973 90.000 90.000 90.000 ZERR 4.00 0.0005 0.0010 0.0009 0.000 0.000 0.000 LATT -1 SYMM 1/2 - X, - Y, 1/2 + Z SYMM - X, 1/2 + Y, 1/2 - Z SYMM 1/2 + X, 1/2 - Y, - Z SFAC C H N O UNIT 80 124 20 4 MERG 2 DELU 0.010 0.010 C5 C6 C11 C8 C9 C10 C11 SIMU 0.040 0.080 1.700 C5 C6 C11 C8 C9 C10 C11 EADP C9 C10 C11 DFIX 0.890 0.020 H2N N2 DFIX 0.890 0.020 N5 H5N FMAP 2 PLAN 5 SIZE 0.070 0.120 0.210 ACTA BOND $H CONF LIST 4 L.S. 50 TEMP 20.00 WGHT 0.079200 0.608200 EXTI 0.005581 FVAR 0.55995 C1 1 0.849511 0.735823 0.357958 11.00000 0.03637 0.08302 = 0.06514 -0.00101 0.00161 0.00139 AFIX 13 H1 2 0.816975 0.737786 0.414449 11.00000 -1.20000 AFIX 0 C2 1 0.734965 0.743199 0.300502 11.00000 0.04265 0.07256 = 0.05618 0.00094 -0.00546 0.00142 C3 1 0.611881 0.762721 0.328121 11.00000 0.05168 0.12399 = 0.05382 -0.00841 0.00011 0.01190 AFIX 43 H3 2 0.595541 0.768384 0.384080 11.00000 -1.20000 AFIX 0 C4 1 0.511792 0.773991 0.272178 11.00000 0.04463 0.11939 = 0.05640 -0.00277 -0.00219 0.00836 C5 1 0.539771 0.762732 0.189116 11.00000 0.04794 0.07532 = 0.05298 0.00310 -0.00257 0.00181 C6 1 0.665709 0.740102 0.167876 11.00000 0.05047 0.10087 = 0.05004 -0.00376 -0.00029 -0.00014 AFIX 43 H6 2 0.684028 0.730795 0.112445 11.00000 -1.20000 AFIX 0 C7 1 0.429983 0.778951 0.130702 11.00000 0.05335 0.10270 = 0.05744 -0.00011 -0.00519 0.00015 AFIX 13 H7 2 0.451606 0.774834 0.072225 11.00000 -1.20000 AFIX 0 C8 1 0.308314 0.712716 0.159064 11.00000 0.05046 0.11662 = 0.07737 0.00631 -0.01540 -0.01236 C9 1 0.287326 0.808097 0.219637 11.00000 0.05324 0.14752 = 0.07557 -0.00593 -0.01179 0.01715 AFIX 13 H9 2 0.196336 0.826751 0.230214 11.00000 -1.20000 AFIX 0 C10 1 0.371533 0.794950 0.296252 11.00000 0.05324 0.14752 = 0.07557 -0.00593 -0.01179 0.01715 AFIX 23 H10A 2 0.366530 0.860102 0.329319 11.00000 -1.20000 H10B 2 0.339417 0.734978 0.328873 11.00000 -1.20000 AFIX 0 C11 1 0.356633 0.881320 0.158707 11.00000 0.05324 0.14752 = 0.07557 -0.00593 -0.01179 0.01715 AFIX 23 H11A 2 0.411379 0.935965 0.183818 11.00000 -1.20000 H11B 2 0.300389 0.912450 0.117195 11.00000 -1.20000 AFIX 0 C12 1 0.328357 0.599969 0.192300 11.00000 0.08429 0.12568 = 0.13549 0.04038 -0.01210 -0.03628 AFIX 137 H12A 2 0.247761 0.572937 0.213693 11.00000 -1.50000 H12B 2 0.392022 0.601840 0.235315 11.00000 -1.50000 H12C 2 0.358041 0.553386 0.149042 11.00000 -1.50000 AFIX 0 C13 1 0.203407 0.712132 0.091437 11.00000 0.06569 0.14551 = 0.10259 -0.00299 -0.02376 -0.01418 AFIX 137 H13A 2 0.228882 0.663481 0.048416 11.00000 -1.50000 H13B 2 0.193871 0.783807 0.069493 11.00000 -1.50000 H13C 2 0.122206 0.688743 0.114331 11.00000 -1.50000 AFIX 0 C14 1 1.088691 0.726105 0.421881 11.00000 0.04152 0.08436 = 0.06042 -0.00324 -0.00686 -0.00356 C15 1 1.071609 0.922647 0.440125 11.00000 0.06429 0.07361 = 0.08023 -0.00883 -0.01806 -0.01008 AFIX 13 H15 2 1.150398 0.910227 0.472528 11.00000 -1.20000 AFIX 0 C15A 1 1.059725 0.530676 0.432141 11.00000 0.06459 0.07280 = 0.07575 -0.00068 -0.01272 0.00623 AFIX 13 H15A 2 1.144657 0.534864 0.459105 11.00000 -1.20000 AFIX 0 C16 1 1.098824 1.014567 0.382686 11.00000 0.07700 0.07844 = 0.13048 0.00879 0.01152 -0.01110 AFIX 137 H16A 2 1.179567 1.001858 0.354843 11.00000 -1.50000 H16B 2 1.104357 1.080836 0.413249 11.00000 -1.50000 H16C 2 1.029987 1.019909 0.343159 11.00000 -1.50000 AFIX 0 C16A 1 1.064034 0.438773 0.371444 11.00000 0.09921 0.09531 = 0.10896 -0.02029 0.00575 0.00925 AFIX 137 H16D 2 0.983176 0.435356 0.342223 11.00000 -1.50000 H16E 2 1.077978 0.371898 0.400121 11.00000 -1.50000 H16F 2 1.133695 0.450501 0.333310 11.00000 -1.50000 AFIX 0 C17 1 0.961026 0.945128 0.500138 11.00000 0.10389 0.10276 = 0.09096 -0.01744 0.01849 -0.00687 AFIX 137 H17A 2 0.880284 0.948126 0.470762 11.00000 -1.50000 H17B 2 0.975947 1.013069 0.527130 11.00000 -1.50000 H17C 2 0.957299 0.888327 0.540268 11.00000 -1.50000 AFIX 0 C17A 1 0.958039 0.508800 0.497810 11.00000 0.11519 0.10881 = 0.06669 0.00794 -0.00464 -0.00171 AFIX 137 H17D 2 0.960168 0.565677 0.537924 11.00000 -1.50000 H17E 2 0.976241 0.440842 0.523961 11.00000 -1.50000 H17F 2 0.873543 0.506077 0.472985 11.00000 -1.50000 AFIX 0 N1 3 0.764449 0.730374 0.220985 11.00000 0.04322 0.09365 = 0.05684 -0.00218 0.00047 0.00044 N2 3 0.915740 0.634458 0.345635 11.00000 0.04948 0.08432 = 0.07548 -0.00863 -0.01996 0.00642 N3 3 1.036743 0.633874 0.389984 11.00000 0.05515 0.07325 = 0.06909 0.00205 -0.01579 0.00894 N4 3 1.046722 0.824191 0.392404 11.00000 0.05433 0.07522 = 0.07200 0.00209 -0.01561 -0.00081 N5 3 0.930064 0.829797 0.344977 11.00000 0.05706 0.09076 = 0.06851 0.00840 -0.01506 0.00102 O1 4 1.176921 0.720921 0.473330 11.00000 0.05082 0.09171 = 0.06461 -0.00100 -0.01238 -0.00211 H2N 2 0.938108 0.629707 0.291670 11.00000 -1.20000 H5N 2 0.945196 0.827875 0.290504 11.00000 -1.20000 HKLF 4 REM ATE69 in P2(1)2(1)2(1) REM R1 = 0.0673 for 1860 Fo > 4sig(Fo) and 0.1506 for all 3694 data REM 236 parameters refined using 33 restraints END WGHT 0.0788 0.6121 REM Highest difference peak 0.189, deepest hole -0.188, 1-sigma level 0.037 Q1 1 0.8603 0.6390 0.4051 11.00000 0.05 0.19 Q2 1 0.8674 0.8500 0.3978 11.00000 0.05 0.19 Q3 1 0.5430 0.6833 0.2224 11.00000 0.05 0.17 Q4 1 0.9665 0.6542 0.4404 11.00000 0.05 0.16 Q5 1 0.9681 0.8062 0.4432 11.00000 0.05 0.15 ; _shelx_res_checksum 54216 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_ATE80 _database_code_depnum_ccdc_archive 'CCDC 1811236' _audit_update_record ; 2017-12-14 deposited with the CCDC. 2018-03-06 downloaded from the CCDC. ; _audit_creation_method SHELXL-2014/7 _shelx_SHELXL_version_number 2014/7 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety '2(C20 H28 Cl2 Cu N5 O)' _chemical_formula_sum 'C20 H28 Cl2 Cu N5 O' _exptl_crystal_recrystallization_method Ethanol _chemical_melting_point ? _exptl_crystal_description block _exptl_crystal_colour purple _diffrn_ambient_temperature 200(2) _chemical_formula_weight 488.91 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_H-M_alt 'P 21' _space_group_name_Hall 'P 2yb' _chemical_absolute_configuration syn loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _cell_length_a 13.0978(9) _cell_length_b 11.0063(7) _cell_length_c 16.8554(14) _cell_angle_alpha 90 _cell_angle_beta 105.955(6) _cell_angle_gamma 90 _cell_volume 2336.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 4951 _cell_measurement_theta_min 1.26 _cell_measurement_theta_max 23.03 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.390 _exptl_crystal_F_000 1016 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.150 _exptl_crystal_size_mid 0.083 _exptl_crystal_size_min 0.040 _exptl_absorpt_coefficient_mu 1.184 _shelx_estimated_absorpt_T_min ? _shelx_estimated_absorpt_T_max ? _exptl_absorpt_correction_type integration _exptl_absorpt_process_details ; STOE X-Red32, absorption correction by Gaussian integration, analogous to P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal Structure Analysis", published in F. R. Ahmed (Editor), "Crystallographic Computing", Munksgaard, Copenhagen (1970), 255 - 270 ; _exptl_absorpt_correction_T_min 0.7442 _exptl_absorpt_correction_T_max 0.8621 _exptl_absorpt_special_details ? _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'sealed X-ray tube, 12x0.4 mm long-fine focus' _diffrn_source_type 'Stoe IPDS2' _diffrn_measurement_device '2-circle diffractometer' _diffrn_measurement_device_type 'STOE IPDS II' _diffrn_measurement_method 'rotation method, \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 30974 _diffrn_reflns_av_unetI/netI 0.2514 _diffrn_reflns_av_R_equivalents 0.3274 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.256 _diffrn_reflns_theta_max 25.196 _diffrn_reflns_theta_full 25.196 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_Laue_measured_fraction_max 0.995 _diffrn_reflns_Laue_measured_fraction_full 0.995 _diffrn_reflns_point_group_measured_fraction_max 0.991 _diffrn_reflns_point_group_measured_fraction_full 0.992 _reflns_number_total 8335 _reflns_number_gt 2991 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.886 _reflns_Friedel_fraction_max 0.988 _reflns_Friedel_fraction_full 0.988 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ? _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0716P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_abs_structure_details ; Classical Flack method preferred over Parsons because s.u. lower. ; _refine_ls_abs_structure_Flack -0.02(7) _refine_ls_number_reflns 8335 _refine_ls_number_parameters 481 _refine_ls_number_restraints 97 _refine_ls_R_factor_all 0.2226 _refine_ls_R_factor_gt 0.0759 _refine_ls_wR_factor_ref 0.2174 _refine_ls_wR_factor_gt 0.1514 _refine_ls_goodness_of_fit_ref 0.913 _refine_ls_restrained_S_all 0.908 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.5128(19) 0.595(3) 0.2647(16) 0.046(6) Uani 1 1 d . U . . . C2 C 0.543(2) 0.591(3) 0.3559(19) 0.053(8) Uani 1 1 d . . . . . C3 C 0.497(2) 0.668(3) 0.406(2) 0.058(8) Uani 1 1 d . . . . . H3 H 0.4446 0.7246 0.3829 0.070 Uiso 1 1 calc R U . . . C4 C 0.5365(19) 0.653(3) 0.4903(19) 0.056(8) Uani 1 1 d . . . . . C5 C 0.6103(17) 0.562(2) 0.5211(15) 0.048(7) Uani 1 1 d . . . . . C6 C 0.6494(19) 0.490(2) 0.4694(18) 0.044(6) Uani 1 1 d . . . . . H6 H 0.6973 0.4276 0.4909 0.052 Uiso 1 1 calc R U . . . C7 C 0.6398(16) 0.5438(19) 0.6132(12) 0.059(5) Uani 1 1 d . . . . . H7 H 0.6904 0.4787 0.6357 0.071 Uiso 1 1 calc R U . . . C8 C 0.6599(17) 0.668(2) 0.6577(14) 0.062(4) Uani 1 1 d . . . . . C9 C 0.5351(15) 0.681(2) 0.6350(12) 0.059(6) Uani 1 1 d . . . . . H9 H 0.5089 0.7237 0.6767 0.070 Uiso 1 1 calc R U . . . C11 C 0.532(2) 0.544(3) 0.640(2) 0.077(7) Uani 1 1 d . . . . . H11A H 0.4720 0.5074 0.5994 0.092 Uiso 1 1 calc R U . . . H11B H 0.5384 0.5126 0.6946 0.092 Uiso 1 1 calc R U . . . C10 C 0.492(2) 0.730(3) 0.5481(17) 0.084(10) Uani 1 1 d . . . . . H10A H 0.5120 0.8139 0.5456 0.101 Uiso 1 1 calc R U . . . H10B H 0.4147 0.7248 0.5317 0.101 Uiso 1 1 calc R U . . . C12 C 0.722(2) 0.763(3) 0.6253(18) 0.079(4) Uani 1 1 d . . . . . H12A H 0.6918 0.7722 0.5669 0.119 Uiso 1 1 calc R U . . . H12B H 0.7186 0.8389 0.6523 0.119 Uiso 1 1 calc R U . . . H12C H 0.7946 0.7376 0.6361 0.119 Uiso 1 1 calc R U . . . C13 C 0.7138(18) 0.659(2) 0.7510(13) 0.079(4) Uani 1 1 d . . . . . H13A H 0.6778 0.6000 0.7752 0.119 Uiso 1 1 calc R U . . . H13B H 0.7867 0.6358 0.7599 0.119 Uiso 1 1 calc R U . . . H13C H 0.7107 0.7371 0.7760 0.119 Uiso 1 1 calc R U . . . C14 C 0.479(2) 0.597(3) 0.1015(19) 0.056(6) Uani 1 1 d . U . . . C15 C 0.421(2) 0.819(2) 0.1053(16) 0.060(3) Uani 1 1 d . . . . . H15 H 0.4096 0.8100 0.0456 0.072 Uiso 1 1 calc R U . . . C15A C 0.491(2) 0.378(3) 0.0988(18) 0.060(3) Uani 1 1 d . . . . . H15A H 0.5302 0.3888 0.0572 0.072 Uiso 1 1 calc R U . . . C16 C 0.316(2) 0.846(3) 0.122(2) 0.090(11) Uani 1 1 d . . . . . H16A H 0.2888 0.9216 0.0963 0.134 Uiso 1 1 calc R U . . . H16B H 0.2663 0.7820 0.0989 0.134 Uiso 1 1 calc R U . . . H16C H 0.3250 0.8508 0.1800 0.134 Uiso 1 1 calc R U . . . C16A C 0.370(2) 0.357(3) 0.053(2) 0.078(10) Uani 1 1 d . . . . . H16D H 0.3424 0.4273 0.0200 0.117 Uiso 1 1 calc R U . . . H16E H 0.3631 0.2872 0.0177 0.117 Uiso 1 1 calc R U . . . H16F H 0.3311 0.3442 0.0927 0.117 Uiso 1 1 calc R U . . . C17 C 0.505(3) 0.918(3) 0.137(2) 0.090(11) Uani 1 1 d . . . . . H17A H 0.4793 0.9939 0.1108 0.136 Uiso 1 1 calc R U . . . H17B H 0.5187 0.9260 0.1955 0.136 Uiso 1 1 calc R U . . . H17C H 0.5695 0.8962 0.1237 0.136 Uiso 1 1 calc R U . . . C17A C 0.534(3) 0.270(3) 0.149(2) 0.088(12) Uani 1 1 d . . . . . H17D H 0.5266 0.2006 0.1140 0.132 Uiso 1 1 calc R U . . . H17E H 0.6071 0.2832 0.1772 0.132 Uiso 1 1 calc R U . . . H17F H 0.4945 0.2575 0.1889 0.132 Uiso 1 1 calc R U . . . C21 C 0.0054(19) 0.422(3) 0.2583(17) 0.045(5) Uani 1 1 d . U . . . C22 C 0.042(2) 0.425(3) 0.3520(16) 0.043(7) Uani 1 1 d . . . . . C23 C 0.013(2) 0.345(3) 0.3995(17) 0.045(7) Uani 1 1 d . . . . . H23 H -0.0411 0.2902 0.3758 0.054 Uiso 1 1 calc R U . . . C24 C 0.059(2) 0.341(3) 0.482(2) 0.061(8) Uani 1 1 d . . . . . C25 C 0.1394(18) 0.429(2) 0.5151(18) 0.056(7) Uani 1 1 d . . . . . C26 C 0.1666(19) 0.507(2) 0.4616(19) 0.049(7) Uani 1 1 d . . . . . H26 H 0.2226 0.5606 0.4826 0.058 Uiso 1 1 calc R U . . . C27 C 0.1991(15) 0.4143(19) 0.6048(11) 0.051(5) Uani 1 1 d . . . . . H27 H 0.2584 0.4703 0.6263 0.062 Uiso 1 1 calc R U . . . C28 C 0.1185(17) 0.398(2) 0.6591(13) 0.062(4) Uani 1 1 d . . . . . C29 C 0.1096(18) 0.2679(19) 0.6299(13) 0.062(6) Uani 1 1 d . . . . . H29 H 0.1008 0.2080 0.6706 0.074 Uiso 1 1 calc R U . . . C30 C 0.030(2) 0.254(3) 0.5422(16) 0.065(7) Uani 1 1 d . . . . . H30A H 0.0322 0.1716 0.5230 0.078 Uiso 1 1 calc R U . . . H30B H -0.0412 0.2713 0.5451 0.078 Uiso 1 1 calc R U . . . C31 C 0.225(2) 0.276(3) 0.618(2) 0.090(10) Uani 1 1 d . . . . . H31A H 0.2812 0.2569 0.6676 0.108 Uiso 1 1 calc R U . . . H31B H 0.2336 0.2334 0.5704 0.108 Uiso 1 1 calc R U . . . C32 C 0.022(2) 0.483(3) 0.6367(19) 0.079(4) Uani 1 1 d . . . . . H32A H 0.0420 0.5614 0.6603 0.119 Uiso 1 1 calc R U . . . H32B H -0.0037 0.4897 0.5778 0.119 Uiso 1 1 calc R U . . . H32C H -0.0332 0.4498 0.6580 0.119 Uiso 1 1 calc R U . . . C33 C 0.1778(18) 0.413(2) 0.7510(13) 0.079(4) Uani 1 1 d . . . . . H33A H 0.1805 0.4980 0.7653 0.119 Uiso 1 1 calc R U . . . H33B H 0.1412 0.3694 0.7841 0.119 Uiso 1 1 calc R U . . . H33C H 0.2487 0.3823 0.7610 0.119 Uiso 1 1 calc R U . . . C34 C -0.038(2) 0.424(3) 0.0946(19) 0.058(6) Uani 1 1 d . U . . . C35 C -0.0992(19) 0.219(2) 0.0928(16) 0.060(3) Uani 1 1 d . . . . . H35 H -0.1068 0.2317 0.0339 0.072 Uiso 1 1 calc R U . . . C35A C -0.022(2) 0.650(3) 0.0968(18) 0.060(3) Uani 1 1 d . . . . . H35A H 0.0085 0.6408 0.0503 0.072 Uiso 1 1 calc R U . . . C36 C -0.020(2) 0.115(3) 0.1250(17) 0.072(10) Uani 1 1 d . . . . . H36A H -0.0472 0.0410 0.0968 0.108 Uiso 1 1 calc R U . . . H36B H 0.0469 0.1342 0.1150 0.108 Uiso 1 1 calc R U . . . H36C H -0.0103 0.1048 0.1831 0.108 Uiso 1 1 calc R U . . . C36A C 0.037(2) 0.750(3) 0.1524(19) 0.065(9) Uani 1 1 d . . . . . H36D H 0.0285 0.8253 0.1223 0.097 Uiso 1 1 calc R U . . . H36E H 0.0100 0.7585 0.1994 0.097 Uiso 1 1 calc R U . . . H36F H 0.1115 0.7300 0.1706 0.097 Uiso 1 1 calc R U . . . C37 C -0.207(2) 0.195(3) 0.1058(19) 0.080(10) Uani 1 1 d . . . . . H37A H -0.2374 0.1242 0.0751 0.120 Uiso 1 1 calc R U . . . H37B H -0.1991 0.1815 0.1634 0.120 Uiso 1 1 calc R U . . . H37C H -0.2521 0.2637 0.0873 0.120 Uiso 1 1 calc R U . . . C37A C -0.138(2) 0.682(3) 0.063(2) 0.100(13) Uani 1 1 d . . . . . H37D H -0.1446 0.7579 0.0334 0.150 Uiso 1 1 calc R U . . . H37E H -0.1738 0.6195 0.0258 0.150 Uiso 1 1 calc R U . . . H37F H -0.1704 0.6899 0.1073 0.150 Uiso 1 1 calc R U . . . Cl1 Cl 0.7531(6) 0.4969(7) 0.2118(6) 0.068(2) Uani 1 1 d . . . . . Cl2 Cl 0.7446(6) 0.2619(7) 0.3610(6) 0.068(2) Uani 1 1 d . . . . . Cl3 Cl 0.2494(6) 0.5354(7) 0.2040(6) 0.068(2) Uani 1 1 d . . . . . Cl4 Cl 0.2381(6) 0.7538(8) 0.3628(6) 0.071(2) Uani 1 1 d . . . . . Cu1 Cu 0.6655(3) 0.4254(2) 0.2962(2) 0.0537(11) Uani 1 1 d . . . . . Cu2 Cu 0.1615(3) 0.5955(2) 0.2929(2) 0.0543(11) Uani 1 1 d . . . . . N1 N 0.6165(16) 0.510(2) 0.3840(14) 0.050(7) Uani 1 1 d . . . . . N2 N 0.5283(16) 0.487(2) 0.2286(13) 0.048(5) Uani 1 1 d . U . . . N3 N 0.4968(17) 0.493(2) 0.1449(14) 0.047(5) Uani 1 1 d . U . . . N4 N 0.4607(17) 0.700(2) 0.1456(15) 0.052(5) Uani 1 1 d . U . . . N5 N 0.4791(18) 0.699(2) 0.2267(15) 0.053(5) Uani 1 1 d . U . . . N6 N 0.1186(16) 0.512(2) 0.3825(15) 0.048(6) Uani 1 1 d . . . . . N7 N 0.0240(17) 0.531(2) 0.2264(15) 0.050(5) Uani 1 1 d . U . . . N8 N -0.0090(18) 0.533(2) 0.1427(16) 0.058(6) Uani 1 1 d . U . . . N9 N -0.0515(18) 0.325(2) 0.1385(14) 0.051(5) Uani 1 1 d . U . . . N10 N -0.0316(17) 0.321(2) 0.2232(14) 0.052(6) Uani 1 1 d . U . . . O1 O 0.4620(15) 0.606(2) 0.0261(13) 0.071(6) Uani 1 1 d . . . . . O2 O -0.0573(17) 0.432(2) 0.0206(13) 0.083(7) Uani 1 1 d . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.042(13) 0.061(13) 0.032(11) -0.011(9) 0.004(11) -0.007(13) C2 0.041(15) 0.06(2) 0.06(2) -0.009(17) 0.013(14) -0.004(16) C3 0.045(14) 0.050(17) 0.08(2) 0.003(16) 0.026(14) 0.007(12) C4 0.045(13) 0.073(18) 0.056(17) -0.005(14) 0.025(12) 0.026(13) C5 0.051(13) 0.053(16) 0.044(14) -0.002(11) 0.017(11) 0.011(11) C6 0.045(12) 0.035(12) 0.056(15) 0.016(11) 0.023(11) 0.001(10) C7 0.066(14) 0.049(12) 0.062(15) 0.003(11) 0.018(11) 0.014(10) C8 0.064(12) 0.079(14) 0.047(9) 0.015(9) 0.019(9) 0.001(9) C9 0.057(12) 0.090(17) 0.040(13) 0.018(11) 0.030(10) 0.008(12) C11 0.085(18) 0.081(19) 0.063(17) -0.002(14) 0.020(14) -0.016(14) C10 0.10(2) 0.10(2) 0.052(17) 0.009(16) 0.018(15) 0.059(18) C12 0.089(10) 0.101(12) 0.049(7) -0.012(8) 0.020(7) 0.008(8) C13 0.089(10) 0.101(12) 0.049(7) -0.012(8) 0.020(7) 0.008(8) C14 0.078(16) 0.055(13) 0.041(13) 0.000(9) 0.026(13) 0.000(14) C15 0.069(7) 0.063(6) 0.044(5) -0.009(9) 0.011(5) 0.000(9) C15A 0.069(7) 0.063(6) 0.044(5) -0.009(9) 0.011(5) 0.000(9) C16 0.074(18) 0.08(2) 0.10(2) 0.026(19) 0.003(17) 0.030(16) C16A 0.075(18) 0.09(2) 0.066(19) -0.015(17) 0.022(15) -0.048(16) C17 0.12(2) 0.056(18) 0.10(2) 0.012(19) 0.04(2) -0.034(18) C17A 0.13(3) 0.07(2) 0.07(3) -0.01(2) 0.03(2) -0.03(2) C21 0.044(13) 0.049(12) 0.050(12) -0.002(9) 0.027(11) 0.011(12) C22 0.050(15) 0.040(16) 0.033(16) 0.000(14) 0.001(13) 0.002(15) C23 0.062(16) 0.041(14) 0.035(15) 0.001(12) 0.018(12) -0.005(12) C24 0.073(17) 0.055(15) 0.055(18) 0.005(13) 0.022(14) 0.002(13) C25 0.055(14) 0.045(14) 0.068(17) -0.004(13) 0.018(12) -0.003(12) C26 0.036(12) 0.048(15) 0.061(18) -0.013(13) 0.014(12) 0.007(10) C27 0.063(12) 0.056(13) 0.032(11) -0.010(10) 0.009(9) 0.013(11) C28 0.064(12) 0.079(14) 0.047(9) 0.015(9) 0.019(9) 0.001(9) C29 0.090(16) 0.051(13) 0.047(14) 0.006(11) 0.023(12) 0.013(12) C30 0.084(18) 0.062(16) 0.050(16) -0.006(12) 0.019(13) -0.016(13) C31 0.10(2) 0.09(2) 0.072(19) 0.031(15) -0.002(15) 0.038(16) C32 0.089(10) 0.101(12) 0.049(7) -0.012(8) 0.020(7) 0.008(8) C33 0.089(10) 0.101(12) 0.049(7) -0.012(8) 0.020(7) 0.008(8) C34 0.060(14) 0.063(14) 0.046(13) 0.014(9) 0.009(12) -0.001(14) C35 0.069(7) 0.063(6) 0.044(5) -0.009(9) 0.011(5) 0.000(9) C35A 0.069(7) 0.063(6) 0.044(5) -0.009(9) 0.011(5) 0.000(9) C36 0.087(18) 0.09(2) 0.027(14) -0.001(15) -0.006(12) -0.008(17) C36A 0.09(2) 0.044(17) 0.06(2) 0.002(17) 0.021(18) -0.007(17) C37 0.069(17) 0.11(2) 0.062(18) -0.035(18) 0.020(14) -0.032(16) C37A 0.09(2) 0.064(19) 0.12(3) 0.05(2) 0.00(2) -0.008(17) Cl1 0.060(5) 0.075(5) 0.078(6) -0.009(4) 0.035(4) -0.004(4) Cl2 0.059(5) 0.059(5) 0.087(7) 0.007(5) 0.022(5) 0.015(4) Cl3 0.065(5) 0.068(5) 0.084(6) -0.011(4) 0.041(4) 0.001(4) Cl4 0.070(5) 0.064(5) 0.083(6) -0.004(5) 0.029(5) -0.011(4) Cu1 0.049(2) 0.057(2) 0.059(3) -0.005(2) 0.0205(19) 0.0009(19) Cu2 0.052(2) 0.056(2) 0.059(3) 0.002(2) 0.022(2) -0.0057(19) N1 0.048(13) 0.065(16) 0.037(14) 0.008(13) 0.009(11) 0.028(12) N2 0.052(12) 0.063(11) 0.034(9) -0.011(9) 0.020(10) 0.014(10) N3 0.062(13) 0.053(10) 0.033(9) -0.006(9) 0.026(10) -0.012(11) N4 0.047(11) 0.056(11) 0.052(11) 0.005(10) 0.011(11) 0.016(10) N5 0.060(13) 0.045(11) 0.052(11) -0.011(10) 0.015(11) -0.016(10) N6 0.034(12) 0.052(15) 0.058(17) 0.010(13) 0.014(11) 0.009(11) N7 0.054(13) 0.038(10) 0.064(11) 0.004(10) 0.024(11) 0.020(9) N8 0.058(14) 0.060(12) 0.062(12) 0.008(11) 0.026(12) 0.002(12) N9 0.054(12) 0.062(12) 0.036(9) 0.002(9) 0.009(10) -0.001(11) N10 0.058(13) 0.064(12) 0.031(9) -0.013(10) 0.010(10) -0.024(11) O1 0.096(13) 0.073(13) 0.045(13) -0.008(10) 0.021(10) -0.009(11) O2 0.104(14) 0.100(16) 0.048(13) 0.005(12) 0.026(11) -0.026(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N5 1.32(3) . ? C1 N2 1.38(3) . ? C1 C2 1.48(4) . ? C2 N1 1.30(3) . ? C2 C3 1.44(4) . ? C3 C4 1.38(4) . ? C3 H3 0.9300 . ? C4 C5 1.39(3) . ? C4 C10 1.52(4) . ? C5 C6 1.38(3) . ? C5 C7 1.50(3) . ? C6 N1 1.40(4) . ? C6 H6 0.9300 . ? C7 C8 1.54(3) . ? C7 C11 1.60(3) . ? C7 H7 0.9800 . ? C8 C12 1.52(4) . ? C8 C13 1.54(3) . ? C8 C9 1.58(3) . ? C9 C10 1.51(3) . ? C9 C11 1.52(4) . ? C9 H9 0.9800 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 O1 1.23(3) . ? C14 N3 1.34(4) . ? C14 N4 1.41(4) . ? C15 N4 1.50(3) . ? C15 C16 1.51(4) . ? C15 C17 1.54(3) . ? C15 H15 0.9800 . ? C15A C17A 1.48(4) . ? C15A N3 1.48(3) . ? C15A C16A 1.58(4) . ? C15A H15A 0.9800 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C16A H16D 0.9600 . ? C16A H16E 0.9600 . ? C16A H16F 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C17A H17D 0.9600 . ? C17A H17E 0.9600 . ? C17A H17F 0.9600 . ? C21 N10 1.29(3) . ? C21 N7 1.36(3) . ? C21 C22 1.52(4) . ? C22 C23 1.32(4) . ? C22 N6 1.37(3) . ? C23 C24 1.36(4) . ? C23 H23 0.9300 . ? C24 C25 1.43(4) . ? C24 C30 1.51(4) . ? C25 C26 1.37(4) . ? C25 C27 1.51(3) . ? C26 N6 1.31(4) . ? C26 H26 0.9300 . ? C27 C31 1.56(3) . ? C27 C28 1.59(3) . ? C27 H27 0.9800 . ? C28 C29 1.51(3) . ? C28 C32 1.53(3) . ? C28 C33 1.54(3) . ? C29 C30 1.56(3) . ? C29 C31 1.57(4) . ? C29 H29 0.9800 . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C33 H33A 0.9600 . ? C33 H33B 0.9600 . ? C33 H33C 0.9600 . ? C34 O2 1.21(3) . ? C34 N9 1.35(4) . ? C34 N8 1.44(4) . ? C35 N9 1.44(3) . ? C35 C37 1.51(3) . ? C35 C36 1.54(3) . ? C35 H35 0.9800 . ? C35A N8 1.48(4) . ? C35A C37A 1.51(4) . ? C35A C36A 1.52(4) . ? C35A H35A 0.9800 . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? C36A H36D 0.9600 . ? C36A H36E 0.9600 . ? C36A H36F 0.9600 . ? C37 H37A 0.9600 . ? C37 H37B 0.9600 . ? C37 H37C 0.9600 . ? C37A H37D 0.9600 . ? C37A H37E 0.9600 . ? C37A H37F 0.9600 . ? Cl1 Cu1 2.204(9) . ? Cl2 Cu1 2.210(9) . ? Cl3 Cu2 2.226(9) . ? Cl4 Cu2 2.186(9) . ? Cu1 N2 1.96(2) . ? Cu1 N1 2.00(2) . ? Cu2 N7 1.97(2) . ? Cu2 N6 1.98(2) . ? N2 N3 1.36(3) . ? N4 N5 1.32(3) . ? N7 N8 1.36(3) . ? N9 N10 1.38(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N5 C1 N2 127(2) . . ? N5 C1 C2 119(3) . . ? N2 C1 C2 114(3) . . ? N1 C2 C3 125(3) . . ? N1 C2 C1 111(3) . . ? C3 C2 C1 124(3) . . ? C4 C3 C2 116(3) . . ? C4 C3 H3 122.1 . . ? C2 C3 H3 122.1 . . ? C3 C4 C5 120(3) . . ? C3 C4 C10 119(2) . . ? C5 C4 C10 121(3) . . ? C6 C5 C4 121(2) . . ? C6 C5 C7 123(2) . . ? C4 C5 C7 116(2) . . ? C5 C6 N1 120(2) . . ? C5 C6 H6 120.2 . . ? N1 C6 H6 120.2 . . ? C5 C7 C8 110.3(18) . . ? C5 C7 C11 106.9(18) . . ? C8 C7 C11 84.7(18) . . ? C5 C7 H7 116.8 . . ? C8 C7 H7 116.8 . . ? C11 C7 H7 116.8 . . ? C12 C8 C13 106(2) . . ? C12 C8 C7 118(2) . . ? C13 C8 C7 114(2) . . ? C12 C8 C9 118(2) . . ? C13 C8 C9 114.0(18) . . ? C7 C8 C9 86.6(16) . . ? C10 C9 C11 113(2) . . ? C10 C9 C8 110.9(18) . . ? C11 C9 C8 86.3(18) . . ? C10 C9 H9 114.6 . . ? C11 C9 H9 114.6 . . ? C8 C9 H9 114.6 . . ? C9 C11 C7 86.9(19) . . ? C9 C11 H11A 114.2 . . ? C7 C11 H11A 114.2 . . ? C9 C11 H11B 114.2 . . ? C7 C11 H11B 114.2 . . ? H11A C11 H11B 111.3 . . ? C9 C10 C4 109(2) . . ? C9 C10 H10A 110.0 . . ? C4 C10 H10A 110.0 . . ? C9 C10 H10B 110.0 . . ? C4 C10 H10B 110.0 . . ? H10A C10 H10B 108.4 . . ? C8 C12 H12A 109.5 . . ? C8 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C8 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C8 C13 H13A 109.5 . . ? C8 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C8 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O1 C14 N3 126(3) . . ? O1 C14 N4 118(3) . . ? N3 C14 N4 115(3) . . ? N4 C15 C16 108(2) . . ? N4 C15 C17 110(2) . . ? C16 C15 C17 114(3) . . ? N4 C15 H15 108.4 . . ? C16 C15 H15 108.4 . . ? C17 C15 H15 108.4 . . ? C17A C15A N3 115(2) . . ? C17A C15A C16A 109(3) . . ? N3 C15A C16A 106(2) . . ? C17A C15A H15A 108.5 . . ? N3 C15A H15A 108.5 . . ? C16A C15A H15A 108.5 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15A C16A H16D 109.5 . . ? C15A C16A H16E 109.5 . . ? H16D C16A H16E 109.5 . . ? C15A C16A H16F 109.5 . . ? H16D C16A H16F 109.5 . . ? H16E C16A H16F 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C15A C17A H17D 109.5 . . ? C15A C17A H17E 109.5 . . ? H17D C17A H17E 109.5 . . ? C15A C17A H17F 109.5 . . ? H17D C17A H17F 109.5 . . ? H17E C17A H17F 109.5 . . ? N10 C21 N7 131(3) . . ? N10 C21 C22 118(3) . . ? N7 C21 C22 110(3) . . ? C23 C22 N6 123(3) . . ? C23 C22 C21 123(3) . . ? N6 C22 C21 113(3) . . ? C22 C23 C24 121(3) . . ? C22 C23 H23 119.3 . . ? C24 C23 H23 119.3 . . ? C23 C24 C25 117(3) . . ? C23 C24 C30 126(3) . . ? C25 C24 C30 117(3) . . ? C26 C25 C24 118(3) . . ? C26 C25 C27 125(2) . . ? C24 C25 C27 116(3) . . ? N6 C26 C25 124(3) . . ? N6 C26 H26 118.0 . . ? C25 C26 H26 118.0 . . ? C25 C27 C31 106(2) . . ? C25 C27 C28 110.3(17) . . ? C31 C27 C28 87(2) . . ? C25 C27 H27 116.4 . . ? C31 C27 H27 116.4 . . ? C28 C27 H27 116.4 . . ? C29 C28 C32 121(2) . . ? C29 C28 C33 113.9(19) . . ? C32 C28 C33 110(2) . . ? C29 C28 C27 85.7(17) . . ? C32 C28 C27 115(2) . . ? C33 C28 C27 109.6(18) . . ? C28 C29 C30 111.8(18) . . ? C28 C29 C31 90(2) . . ? C30 C29 C31 107(2) . . ? C28 C29 H29 115.0 . . ? C30 C29 H29 115.0 . . ? C31 C29 H29 115.0 . . ? C24 C30 C29 111(2) . . ? C24 C30 H30A 109.5 . . ? C29 C30 H30A 109.5 . . ? C24 C30 H30B 109.5 . . ? C29 C30 H30B 109.5 . . ? H30A C30 H30B 108.1 . . ? C27 C31 C29 84.2(18) . . ? C27 C31 H31A 114.6 . . ? C29 C31 H31A 114.6 . . ? C27 C31 H31B 114.6 . . ? C29 C31 H31B 114.6 . . ? H31A C31 H31B 111.7 . . ? C28 C32 H32A 109.5 . . ? C28 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C28 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C28 C33 H33A 109.5 . . ? C28 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C28 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? O2 C34 N9 127(3) . . ? O2 C34 N8 118(3) . . ? N9 C34 N8 115(3) . . ? N9 C35 C37 110(2) . . ? N9 C35 C36 105(2) . . ? C37 C35 C36 113(3) . . ? N9 C35 H35 109.5 . . ? C37 C35 H35 109.5 . . ? C36 C35 H35 109.5 . . ? N8 C35A C37A 111(2) . . ? N8 C35A C36A 110(2) . . ? C37A C35A C36A 111(2) . . ? N8 C35A H35A 108.2 . . ? C37A C35A H35A 108.2 . . ? C36A C35A H35A 108.2 . . ? C35 C36 H36A 109.5 . . ? C35 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C35 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C35A C36A H36D 109.5 . . ? C35A C36A H36E 109.5 . . ? H36D C36A H36E 109.5 . . ? C35A C36A H36F 109.5 . . ? H36D C36A H36F 109.5 . . ? H36E C36A H36F 109.5 . . ? C35 C37 H37A 109.5 . . ? C35 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C35 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C35A C37A H37D 109.5 . . ? C35A C37A H37E 109.5 . . ? H37D C37A H37E 109.5 . . ? C35A C37A H37F 109.5 . . ? H37D C37A H37F 109.5 . . ? H37E C37A H37F 109.5 . . ? N2 Cu1 N1 80.8(8) . . ? N2 Cu1 Cl1 93.3(7) . . ? N1 Cu1 Cl1 129.9(8) . . ? N2 Cu1 Cl2 142.8(7) . . ? N1 Cu1 Cl2 102.5(7) . . ? Cl1 Cu1 Cl2 110.7(3) . . ? N7 Cu2 N6 81.9(10) . . ? N7 Cu2 Cl4 143.6(6) . . ? N6 Cu2 Cl4 98.2(8) . . ? N7 Cu2 Cl3 94.1(7) . . ? N6 Cu2 Cl3 133.2(7) . . ? Cl4 Cu2 Cl3 110.8(3) . . ? C2 N1 C6 118(3) . . ? C2 N1 Cu1 114(2) . . ? C6 N1 Cu1 127.9(18) . . ? N3 N2 C1 112(2) . . ? N3 N2 Cu1 126.1(17) . . ? C1 N2 Cu1 105.3(17) . . ? C14 N3 N2 125(2) . . ? C14 N3 C15A 118(2) . . ? N2 N3 C15A 117(2) . . ? N5 N4 C14 122(3) . . ? N5 N4 C15 115(2) . . ? C14 N4 C15 123(2) . . ? N4 N5 C1 117(2) . . ? C26 N6 C22 117(3) . . ? C26 N6 Cu2 130(2) . . ? C22 N6 Cu2 112(2) . . ? N8 N7 C21 113(2) . . ? N8 N7 Cu2 124(2) . . ? C21 N7 Cu2 109.1(18) . . ? N7 N8 C34 122(3) . . ? N7 N8 C35A 121(2) . . ? C34 N8 C35A 117(2) . . ? C34 N9 N10 125(3) . . ? C34 N9 C35 117(2) . . ? N10 N9 C35 117(2) . . ? C21 N10 N9 113(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N5 C1 C2 N1 -150(3) . . . . ? N2 C1 C2 N1 27(4) . . . . ? N5 C1 C2 C3 30(4) . . . . ? N2 C1 C2 C3 -153(3) . . . . ? N1 C2 C3 C4 1(5) . . . . ? C1 C2 C3 C4 -179(3) . . . . ? C2 C3 C4 C5 -4(4) . . . . ? C2 C3 C4 C10 -179(2) . . . . ? C3 C4 C5 C6 3(4) . . . . ? C10 C4 C5 C6 178(2) . . . . ? C3 C4 C5 C7 -174(2) . . . . ? C10 C4 C5 C7 1(4) . . . . ? C4 C5 C6 N1 2(4) . . . . ? C7 C5 C6 N1 179(2) . . . . ? C6 C5 C7 C8 138(2) . . . . ? C4 C5 C7 C8 -45(3) . . . . ? C6 C5 C7 C11 -131(2) . . . . ? C4 C5 C7 C11 46(3) . . . . ? C5 C7 C8 C12 -42(3) . . . . ? C11 C7 C8 C12 -148(2) . . . . ? C5 C7 C8 C13 -167.2(18) . . . . ? C11 C7 C8 C13 87(2) . . . . ? C5 C7 C8 C9 77.9(18) . . . . ? C11 C7 C8 C9 -28.2(17) . . . . ? C12 C8 C9 C10 37(3) . . . . ? C13 C8 C9 C10 161(2) . . . . ? C7 C8 C9 C10 -83(2) . . . . ? C12 C8 C9 C11 150(3) . . . . ? C13 C8 C9 C11 -85(2) . . . . ? C7 C8 C9 C11 29.9(19) . . . . ? C10 C9 C11 C7 82(2) . . . . ? C8 C9 C11 C7 -28.7(16) . . . . ? C5 C7 C11 C9 -80(2) . . . . ? C8 C7 C11 C9 29.6(17) . . . . ? C11 C9 C10 C4 -45(3) . . . . ? C8 C9 C10 C4 50(3) . . . . ? C3 C4 C10 C9 171(3) . . . . ? C5 C4 C10 C9 -4(4) . . . . ? N10 C21 C22 C23 -20(4) . . . . ? N7 C21 C22 C23 164(2) . . . . ? N10 C21 C22 N6 154(2) . . . . ? N7 C21 C22 N6 -23(3) . . . . ? N6 C22 C23 C24 -2(4) . . . . ? C21 C22 C23 C24 171(3) . . . . ? C22 C23 C24 C25 1(4) . . . . ? C22 C23 C24 C30 179(3) . . . . ? C23 C24 C25 C26 -2(4) . . . . ? C30 C24 C25 C26 180(2) . . . . ? C23 C24 C25 C27 -173(2) . . . . ? C30 C24 C25 C27 9(3) . . . . ? C24 C25 C26 N6 5(4) . . . . ? C27 C25 C26 N6 175(2) . . . . ? C26 C25 C27 C31 -127(3) . . . . ? C24 C25 C27 C31 44(3) . . . . ? C26 C25 C27 C28 140(2) . . . . ? C24 C25 C27 C28 -50(3) . . . . ? C25 C27 C28 C29 79(2) . . . . ? C31 C27 C28 C29 -27.1(17) . . . . ? C25 C27 C28 C32 -43(3) . . . . ? C31 C27 C28 C32 -149(2) . . . . ? C25 C27 C28 C33 -167(2) . . . . ? C31 C27 C28 C33 87(2) . . . . ? C32 C28 C29 C30 35(3) . . . . ? C33 C28 C29 C30 168.7(19) . . . . ? C27 C28 C29 C30 -82(2) . . . . ? C32 C28 C29 C31 144(3) . . . . ? C33 C28 C29 C31 -83(2) . . . . ? C27 C28 C29 C31 26.9(16) . . . . ? C23 C24 C30 C29 174(3) . . . . ? C25 C24 C30 C29 -8(3) . . . . ? C28 C29 C30 C24 53(3) . . . . ? C31 C29 C30 C24 -44(3) . . . . ? C25 C27 C31 C29 -84(2) . . . . ? C28 C27 C31 C29 25.9(16) . . . . ? C28 C29 C31 C27 -27.3(17) . . . . ? C30 C29 C31 C27 85(2) . . . . ? C3 C2 N1 C6 4(4) . . . . ? C1 C2 N1 C6 -176(2) . . . . ? C3 C2 N1 Cu1 -178(2) . . . . ? C1 C2 N1 Cu1 3(3) . . . . ? C5 C6 N1 C2 -5(4) . . . . ? C5 C6 N1 Cu1 176.7(17) . . . . ? N5 C1 N2 N3 -5(4) . . . . ? C2 C1 N2 N3 179(2) . . . . ? N5 C1 N2 Cu1 135(3) . . . . ? C2 C1 N2 Cu1 -41(3) . . . . ? O1 C14 N3 N2 171(3) . . . . ? N4 C14 N3 N2 -19(4) . . . . ? O1 C14 N3 C15A -3(4) . . . . ? N4 C14 N3 C15A 166(2) . . . . ? C1 N2 N3 C14 16(4) . . . . ? Cu1 N2 N3 C14 -114(3) . . . . ? C1 N2 N3 C15A -169(2) . . . . ? Cu1 N2 N3 C15A 60(3) . . . . ? C17A C15A N3 C14 168(3) . . . . ? C16A C15A N3 C14 -71(3) . . . . ? C17A C15A N3 N2 -7(4) . . . . ? C16A C15A N3 N2 114(2) . . . . ? O1 C14 N4 N5 -178(3) . . . . ? N3 C14 N4 N5 11(4) . . . . ? O1 C14 N4 C15 1(4) . . . . ? N3 C14 N4 C15 -169(2) . . . . ? C16 C15 N4 N5 -62(3) . . . . ? C17 C15 N4 N5 62(3) . . . . ? C16 C15 N4 C14 118(3) . . . . ? C17 C15 N4 C14 -117(3) . . . . ? C14 N4 N5 C1 -2(4) . . . . ? C15 N4 N5 C1 179(2) . . . . ? N2 C1 N5 N4 -2(4) . . . . ? C2 C1 N5 N4 175(3) . . . . ? C25 C26 N6 C22 -5(4) . . . . ? C25 C26 N6 Cu2 -167.4(18) . . . . ? C23 C22 N6 C26 4(4) . . . . ? C21 C22 N6 C26 -169(2) . . . . ? C23 C22 N6 Cu2 169(2) . . . . ? C21 C22 N6 Cu2 -4(3) . . . . ? N10 C21 N7 N8 5(4) . . . . ? C22 C21 N7 N8 -179(2) . . . . ? N10 C21 N7 Cu2 -138(3) . . . . ? C22 C21 N7 Cu2 38(2) . . . . ? C21 N7 N8 C34 -13(4) . . . . ? Cu2 N7 N8 C34 123(2) . . . . ? C21 N7 N8 C35A 164(2) . . . . ? Cu2 N7 N8 C35A -61(3) . . . . ? O2 C34 N8 N7 -173(3) . . . . ? N9 C34 N8 N7 13(4) . . . . ? O2 C34 N8 C35A 10(4) . . . . ? N9 C34 N8 C35A -164(2) . . . . ? C37A C35A N8 N7 -105(3) . . . . ? C36A C35A N8 N7 18(4) . . . . ? C37A C35A N8 C34 71(3) . . . . ? C36A C35A N8 C34 -165(2) . . . . ? O2 C34 N9 N10 -178(3) . . . . ? N8 C34 N9 N10 -5(4) . . . . ? O2 C34 N9 C35 -4(5) . . . . ? N8 C34 N9 C35 169(2) . . . . ? C37 C35 N9 C34 -113(3) . . . . ? C36 C35 N9 C34 125(3) . . . . ? C37 C35 N9 N10 61(3) . . . . ? C36 C35 N9 N10 -60(3) . . . . ? N7 C21 N10 N9 3(4) . . . . ? C22 C21 N10 N9 -173(2) . . . . ? C34 N9 N10 C21 -2(4) . . . . ? C35 N9 N10 C21 -176(2) . . . . ? _refine_diff_density_max 0.556 _refine_diff_density_min -0.459 _refine_diff_density_rms 0.097 _shelx_res_file ; shelx.res created by SHELXL-2014/7 TITL ATE80 in P2(1) CELL 0.71073 13.0978 11.0063 16.8554 90.000 105.955 90.000 ZERR 2.00 0.0009 0.0007 0.0014 0.000 0.006 0.000 LATT -1 SYMM - X, 1/2 + Y, - Z SFAC C H CL CU N O UNIT 80 112 8 4 20 4 MERG 2 EADP C12 C13 C32 C33 DELU 0.010 0.010 C1 C14 N2 N3 N4 N5 SIMU 0.040 0.080 1.700 C1 C14 N2 N3 N4 N5 DELU 0.010 0.010 C21 C34 N7 N8 N9 N10 SIMU 0.040 0.080 1.700 C21 C34 N7 N8 N9 N10 EADP C15 C15A C35 C35A EADP C8 C28 EADP C12 C13 C32 C33 FMAP 2 PLAN 5 ACTA BOND $H CONF LIST 4 L.S. 99 WGHT 0.071600 FVAR 0.39874 C1 1 0.512830 0.595189 0.264691 11.00000 0.04195 0.06120 = 0.03158 -0.01142 0.00385 -0.00690 C2 1 0.543453 0.591493 0.355889 11.00000 0.04103 0.05964 = 0.05784 -0.00907 0.01302 -0.00402 C3 1 0.497342 0.668320 0.405906 11.00000 0.04538 0.04987 = 0.08365 0.00337 0.02625 0.00667 AFIX 43 H3 2 0.444559 0.724643 0.382948 11.00000 -1.20000 AFIX 0 C4 1 0.536480 0.653106 0.490267 11.00000 0.04508 0.07300 = 0.05630 -0.00506 0.02521 0.02591 C5 1 0.610269 0.561704 0.521134 11.00000 0.05146 0.05256 = 0.04385 -0.00151 0.01732 0.01100 C6 1 0.649405 0.489524 0.469354 11.00000 0.04536 0.03503 = 0.05583 0.01639 0.02262 0.00142 AFIX 43 H6 2 0.697323 0.427611 0.490907 11.00000 -1.20000 AFIX 0 C7 1 0.639762 0.543808 0.613160 11.00000 0.06563 0.04916 = 0.06205 0.00297 0.01815 0.01358 AFIX 13 H7 2 0.690416 0.478655 0.635739 11.00000 -1.20000 AFIX 0 C8 1 0.659850 0.667573 0.657662 11.00000 0.06353 0.07873 = 0.04732 0.01469 0.01878 0.00146 C9 1 0.535088 0.681479 0.635043 11.00000 0.05654 0.08952 = 0.03951 0.01759 0.02986 0.00760 AFIX 13 H9 2 0.508900 0.723747 0.676734 11.00000 -1.20000 AFIX 0 C11 1 0.531572 0.544104 0.639628 11.00000 0.08537 0.08090 = 0.06327 -0.00180 0.02024 -0.01641 AFIX 23 H11A 2 0.471953 0.507438 0.599426 11.00000 -1.20000 H11B 2 0.538428 0.512585 0.694589 11.00000 -1.20000 AFIX 0 C10 1 0.491617 0.729534 0.548095 11.00000 0.09852 0.09988 = 0.05206 0.00867 0.01795 0.05906 AFIX 23 H10A 2 0.511977 0.813880 0.545585 11.00000 -1.20000 H10B 2 0.414701 0.724846 0.531711 11.00000 -1.20000 AFIX 0 C12 1 0.721919 0.762820 0.625259 11.00000 0.08933 0.10089 = 0.04880 -0.01249 0.02039 0.00760 AFIX 33 H12A 2 0.691797 0.772177 0.566863 11.00000 -1.50000 H12B 2 0.718594 0.838913 0.652277 11.00000 -1.50000 H12C 2 0.794636 0.737631 0.636136 11.00000 -1.50000 AFIX 0 C13 1 0.713846 0.659326 0.750971 11.00000 0.08933 0.10089 = 0.04880 -0.01249 0.02039 0.00760 AFIX 33 H13A 2 0.677841 0.599995 0.775206 11.00000 -1.50000 H13B 2 0.786704 0.635779 0.759873 11.00000 -1.50000 H13C 2 0.710662 0.737061 0.776013 11.00000 -1.50000 AFIX 0 C14 1 0.478607 0.596572 0.101460 11.00000 0.07780 0.05519 = 0.04085 -0.00029 0.02637 0.00042 C15 1 0.421067 0.818676 0.105314 11.00000 0.06920 0.06334 = 0.04368 -0.00922 0.01096 -0.00027 AFIX 13 H15 2 0.409617 0.809989 0.045640 11.00000 -1.20000 AFIX 0 C15A 1 0.491232 0.378445 0.098779 11.00000 0.06920 0.06334 = 0.04368 -0.00922 0.01096 -0.00027 AFIX 13 H15A 2 0.530225 0.388773 0.057246 11.00000 -1.20000 AFIX 0 C16 1 0.315690 0.845746 0.121609 11.00000 0.07390 0.08361 = 0.09919 0.02608 0.00318 0.02986 AFIX 33 H16A 2 0.288767 0.921639 0.096279 11.00000 -1.50000 H16B 2 0.266259 0.782013 0.098883 11.00000 -1.50000 H16C 2 0.325011 0.850804 0.180031 11.00000 -1.50000 AFIX 0 C16A 1 0.370080 0.357187 0.052768 11.00000 0.07478 0.09352 = 0.06625 -0.01511 0.02179 -0.04820 AFIX 33 H16D 2 0.342363 0.427259 0.019988 11.00000 -1.50000 H16E 2 0.363139 0.287202 0.017691 11.00000 -1.50000 H16F 2 0.331145 0.344187 0.092676 11.00000 -1.50000 AFIX 0 C17 1 0.505008 0.918022 0.136774 11.00000 0.12044 0.05611 = 0.09801 0.01185 0.03567 -0.03428 AFIX 33 H17A 2 0.479294 0.993901 0.110792 11.00000 -1.50000 H17B 2 0.518661 0.925990 0.195482 11.00000 -1.50000 H17C 2 0.569467 0.896190 0.123686 11.00000 -1.50000 AFIX 0 C17A 1 0.533555 0.270485 0.149119 11.00000 0.12734 0.07156 = 0.06888 -0.00986 0.03413 -0.02617 AFIX 33 H17D 2 0.526557 0.200571 0.113974 11.00000 -1.50000 H17E 2 0.607144 0.283189 0.177174 11.00000 -1.50000 H17F 2 0.494480 0.257510 0.188936 11.00000 -1.50000 AFIX 0 C21 1 0.005350 0.421999 0.258323 11.00000 0.04412 0.04861 = 0.04966 -0.00228 0.02685 0.01060 C22 1 0.042467 0.425491 0.351995 11.00000 0.04965 0.04001 = 0.03304 -0.00017 0.00118 0.00250 C23 1 0.012627 0.344997 0.399468 11.00000 0.06192 0.04094 = 0.03511 0.00082 0.01775 -0.00492 AFIX 43 H23 2 -0.041138 0.290174 0.375771 11.00000 -1.20000 AFIX 0 C24 1 0.058800 0.340738 0.481988 11.00000 0.07343 0.05538 = 0.05537 0.00532 0.02206 0.00244 C25 1 0.139433 0.428784 0.515104 11.00000 0.05464 0.04487 = 0.06820 -0.00364 0.01792 -0.00317 C26 1 0.166595 0.507277 0.461565 11.00000 0.03631 0.04815 = 0.06142 -0.01334 0.01386 0.00716 AFIX 43 H26 2 0.222579 0.560617 0.482558 11.00000 -1.20000 AFIX 0 C27 1 0.199130 0.414256 0.604833 11.00000 0.06322 0.05637 = 0.03199 -0.00973 0.00879 0.01315 AFIX 13 H27 2 0.258426 0.470306 0.626343 11.00000 -1.20000 AFIX 0 C28 1 0.118499 0.397855 0.659084 11.00000 0.06353 0.07873 = 0.04732 0.01469 0.01878 0.00146 C29 1 0.109570 0.267859 0.629917 11.00000 0.09018 0.05138 = 0.04687 0.00555 0.02264 0.01291 AFIX 13 H29 2 0.100826 0.208013 0.670601 11.00000 -1.20000 AFIX 0 C30 1 0.030366 0.254390 0.542218 11.00000 0.08376 0.06228 = 0.04971 -0.00586 0.01938 -0.01576 AFIX 23 H30A 2 0.032238 0.171554 0.523021 11.00000 -1.20000 H30B 2 -0.041207 0.271264 0.545119 11.00000 -1.20000 AFIX 0 C31 1 0.224586 0.275790 0.618440 11.00000 0.09794 0.08544 = 0.07207 0.03149 -0.00228 0.03757 AFIX 23 H31A 2 0.281200 0.256890 0.667551 11.00000 -1.20000 H31B 2 0.233583 0.233389 0.570361 11.00000 -1.20000 AFIX 0 C32 1 0.021860 0.482587 0.636672 11.00000 0.08933 0.10089 = 0.04880 -0.01249 0.02039 0.00760 AFIX 33 H32A 2 0.041959 0.561352 0.660282 11.00000 -1.50000 H32B 2 -0.003661 0.489671 0.577752 11.00000 -1.50000 H32C 2 -0.033214 0.449783 0.657952 11.00000 -1.50000 AFIX 0 C33 1 0.177819 0.413347 0.751036 11.00000 0.08933 0.10089 = 0.04880 -0.01249 0.02039 0.00760 AFIX 33 H33A 2 0.180535 0.497951 0.765317 11.00000 -1.50000 H33B 2 0.141151 0.369395 0.784065 11.00000 -1.50000 H33C 2 0.248739 0.382350 0.761031 11.00000 -1.50000 AFIX 0 C34 1 -0.038387 0.423685 0.094642 11.00000 0.06037 0.06307 = 0.04646 0.01422 0.00876 -0.00063 C35 1 -0.099203 0.218972 0.092815 11.00000 0.06920 0.06334 = 0.04368 -0.00922 0.01096 -0.00027 AFIX 13 H35 2 -0.106797 0.231705 0.033929 11.00000 -1.20000 AFIX 0 C35A 1 -0.022336 0.649918 0.096771 11.00000 0.06920 0.06334 = 0.04368 -0.00922 0.01096 -0.00027 AFIX 13 H35A 2 0.008496 0.640771 0.050308 11.00000 -1.20000 AFIX 0 C36 1 -0.020006 0.114928 0.124966 11.00000 0.08660 0.08976 = 0.02720 -0.00064 -0.00579 -0.00757 AFIX 33 H36A 2 -0.047236 0.041010 0.096784 11.00000 -1.50000 H36B 2 0.046896 0.134171 0.115017 11.00000 -1.50000 H36C 2 -0.010311 0.104751 0.183137 11.00000 -1.50000 AFIX 0 C36A 1 0.037371 0.750128 0.152366 11.00000 0.09220 0.04361 = 0.05878 0.00229 0.02147 -0.00712 AFIX 33 H36D 2 0.028451 0.825288 0.122340 11.00000 -1.50000 H36E 2 0.009958 0.758514 0.199373 11.00000 -1.50000 H36F 2 0.111471 0.729971 0.170553 11.00000 -1.50000 AFIX 0 C37 1 -0.206716 0.194921 0.105824 11.00000 0.06898 0.11116 = 0.06166 -0.03463 0.01961 -0.03223 AFIX 33 H37A 2 -0.237422 0.124212 0.075064 11.00000 -1.50000 H37B 2 -0.199146 0.181533 0.163436 11.00000 -1.50000 H37C 2 -0.252071 0.263696 0.087260 11.00000 -1.50000 AFIX 0 C37A 1 -0.138403 0.682251 0.062680 11.00000 0.09183 0.06393 = 0.12475 0.05408 -0.00402 -0.00831 AFIX 33 H37D 2 -0.144586 0.757891 0.033377 11.00000 -1.50000 H37E 2 -0.173845 0.619463 0.025754 11.00000 -1.50000 H37F 2 -0.170447 0.689921 0.107271 11.00000 -1.50000 AFIX 0 CL1 3 0.753078 0.496943 0.211789 11.00000 0.05955 0.07513 = 0.07845 -0.00872 0.03487 -0.00431 CL2 3 0.744586 0.261910 0.361047 11.00000 0.05944 0.05899 = 0.08733 0.00749 0.02190 0.01462 CL3 3 0.249432 0.535361 0.203988 11.00000 0.06465 0.06807 = 0.08397 -0.01061 0.04117 0.00135 CL4 3 0.238094 0.753796 0.362792 11.00000 0.07001 0.06402 = 0.08280 -0.00395 0.02925 -0.01104 CU1 4 0.665520 0.425373 0.296193 11.00000 0.04909 0.05668 = 0.05880 -0.00485 0.02054 0.00092 CU2 4 0.161549 0.595494 0.292874 11.00000 0.05208 0.05556 = 0.05944 0.00202 0.02211 -0.00568 N1 5 0.616487 0.510083 0.384012 11.00000 0.04802 0.06483 = 0.03693 0.00814 0.00893 0.02823 N2 5 0.528326 0.486804 0.228610 11.00000 0.05175 0.06259 = 0.03370 -0.01131 0.01985 0.01366 N3 5 0.496824 0.493393 0.144919 11.00000 0.06218 0.05289 = 0.03292 -0.00572 0.02628 -0.01205 N4 5 0.460674 0.699898 0.145626 11.00000 0.04715 0.05614 = 0.05152 0.00542 0.01141 0.01575 N5 5 0.479130 0.698617 0.226681 11.00000 0.06001 0.04549 = 0.05190 -0.01138 0.01460 -0.01629 N6 5 0.118636 0.512053 0.382455 11.00000 0.03413 0.05208 = 0.05783 0.00987 0.01380 0.00873 N7 5 0.024022 0.530963 0.226366 11.00000 0.05360 0.03798 = 0.06430 0.00381 0.02419 0.02020 N8 5 -0.009013 0.533306 0.142666 11.00000 0.05779 0.05950 = 0.06213 0.00778 0.02588 0.00166 N9 5 -0.051509 0.324932 0.138505 11.00000 0.05396 0.06166 = 0.03606 0.00177 0.00907 -0.00057 N10 5 -0.031610 0.321343 0.223172 11.00000 0.05800 0.06431 = 0.03128 -0.01268 0.01025 -0.02433 O1 6 0.462010 0.605840 0.026081 11.00000 0.09572 0.07259 = 0.04545 -0.00767 0.02051 -0.00910 O2 6 -0.057311 0.431827 0.020613 11.00000 0.10442 0.10036 = 0.04759 0.00520 0.02553 -0.02554 HKLF 4 REM ATE80 in P2(1) REM R1 = 0.0759 for 2991 Fo > 4sig(Fo) and 0.2226 for all 8335 data REM 481 parameters refined using 97 restraints END WGHT 0.0709 0.0000 REM Highest difference peak 0.556, deepest hole -0.459, 1-sigma level 0.097 Q1 1 0.7876 0.3708 0.3406 11.00000 0.05 0.56 Q2 1 0.2832 0.6529 0.3396 11.00000 0.05 0.54 Q3 1 0.3990 0.6459 0.3630 11.00000 0.05 0.40 Q4 1 0.6180 0.3065 0.3171 11.00000 0.05 0.39 Q5 1 0.4724 0.3727 0.2568 11.00000 0.05 0.36 ; _shelx_res_checksum 62164 # start Validation Reply Form _vrf_RINTA01_ATE80 ; PROBLEM: The value of Rint is greater than 0.25 RESPONSE: The overall quality of the data are poor due to the crystal quality/instability ; _vrf_PLAT020_ATE80 ; PROBLEM: The value of Rint is greater than 0.12 ......... 0.327 Report RESPONSE: The overall quality of the data are poor due to the crystal quality/instability ; _vrf_PLAT026_ATE80 ; PROBLEM: Ratio Observed / Unique Reflections (too) Low .. 36 % RESPONSE: low diffraction intensities in general and specially after 2theta of 45 ; _vrf_PLAT341_ATE80 ; PROBLEM: Low Bond Precision on C-C Bonds ............... 0.03722 Ang. RESPONSE: The overall quality of the data are poor due to the crystal quality/instability ; # end Validation Reply Form ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_45-ald _database_code_depnum_ccdc_archive 'CCDC 1532177' _audit_update_record ; 2017-12-14 deposited with the CCDC. 2018-03-06 downloaded from the CCDC. ; _audit_creation_method SHELXL-2014/7 _shelx_SHELXL_version_number 2014/7 _chemical_name_systematic (6R,8R)-7,7-dimethyl-5,6,7,8-tetrahydro-6,8-methanoisoquinoline-3-carbaldehyde _chemical_name_common ? _chemical_formula_moiety 'C13 H15 N O' _chemical_formula_sum 'C13 H15 N O' _exptl_crystal_recrystallization_method ethylacetate _chemical_melting_point ? _exptl_crystal_description cube _exptl_crystal_colour yellow _diffrn_ambient_temperature 200(2) _chemical_formula_weight 201.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system tetragonal _space_group_IT_number 96 _space_group_name_H-M_alt 'P 43 21 2' _space_group_name_Hall 'P 4nw 2abw' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-y+1/2, x+1/2, z+3/4' '-x, -y, z+1/2' 'y+1/2, -x+1/2, z+1/4' 'x+1/2, -y+1/2, -z+1/4' 'y, x, -z' '-x+1/2, y+1/2, -z+3/4' '-y, -x, -z+1/2' _cell_length_a 7.5168(4) _cell_length_b 7.5168(4) _cell_length_c 39.316(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2221.4(3) _cell_formula_units_Z 8 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 8511 _cell_measurement_theta_min 2.07 _cell_measurement_theta_max 23.78 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.204 _exptl_crystal_F_000 864 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.130 _exptl_crystal_size_mid 0.120 _exptl_crystal_size_min 0.110 _exptl_absorpt_coefficient_mu 0.076 _shelx_estimated_absorpt_T_min 0.990 _shelx_estimated_absorpt_T_max 0.992 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details ; STOE X-Red32, absorption correction by Gaussian integration, analogous to P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal Structure Analysis", published in F. R. Ahmed (Editor), "Crystallographic Computing", Munksgaard, Copenhagen (1970), 255 - 270 ; _exptl_absorpt_correction_T_min 0.9543 _exptl_absorpt_correction_T_max 0.9911 _exptl_absorpt_special_details ? _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'sealed X-ray tube, 12x0.4 mm long-fine focus' _diffrn_measurement_device '2-circle diffractometer' _diffrn_measurement_device_type 'STOE IPDS II' _diffrn_measurement_method 'rotation method, \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 28194 _diffrn_reflns_av_unetI/netI 0.0331 _diffrn_reflns_av_R_equivalents 0.1169 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -46 _diffrn_reflns_limit_l_max 46 _diffrn_reflns_theta_min 2.072 _diffrn_reflns_theta_max 25.156 _diffrn_reflns_theta_full 25.156 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_point_group_measured_fraction_full 1.000 _reflns_number_total 1977 _reflns_number_gt 1336 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.563 _reflns_Friedel_fraction_max 1.000 _reflns_Friedel_fraction_full 1.001 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refined as a 2-component inversion twin. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=exp[3.0000(sin\q/\l)^2^)]/[\s^2^(Fo^2^)+(0.0892P)^2^+0.0400] where P=(0.1000Fo^2^+0.9000Fc^2^)' _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method 'SHELXL-2014/7 (Sheldrick 2014' _refine_ls_extinction_coef 0.020(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details ; Refined as an inversion twin. The Flack parameter was meaningless, -3(5), and has been erased. ; _symmetry_cell_setting tetragonal _symmetry_space_group_name_h-m 'P 43 21 2' _symmetry_int_tables_number 96 _chemical_absolute_configuration syn _refine_ls_number_reflns 1977 _refine_ls_number_parameters 140 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0797 _refine_ls_R_factor_gt 0.0507 _refine_ls_wR_factor_ref 0.1564 _refine_ls_wR_factor_gt 0.1283 _refine_ls_goodness_of_fit_ref 1.384 _refine_ls_restrained_S_all 1.384 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4848(6) -0.1973(6) 0.08465(11) 0.0834(11) Uani 1 1 d . . . . . H1 H 0.6044 -0.2012 0.0769 0.100 Uiso 1 1 calc R U . . . C2 C 0.3828(5) -0.0350(5) 0.07750(9) 0.0660(9) Uani 1 1 d . . . . . C3 C 0.2113(5) -0.0106(5) 0.08916(9) 0.0662(9) Uani 1 1 d . . . . . H3 H 0.1563 -0.0993 0.1028 0.079 Uiso 1 1 calc R U . . . C4 C 0.1200(4) 0.1426(5) 0.08098(8) 0.0606(8) Uani 1 1 d . . . . . C5 C 0.2087(4) 0.2689(5) 0.06088(8) 0.0616(8) Uani 1 1 d . . . . . C6 C 0.3820(5) 0.2333(5) 0.05095(9) 0.0700(10) Uani 1 1 d . . . . . H6 H 0.4417 0.3205 0.0377 0.084 Uiso 1 1 calc R U . . . C7 C 0.1084(5) 0.4333(5) 0.05233(9) 0.0697(9) Uani 1 1 d . . . . . H7 H 0.1734 0.5241 0.0385 0.084 Uiso 1 1 calc R U . . . C8 C -0.0842(5) 0.3850(5) 0.04007(8) 0.0678(9) Uani 1 1 d . . . . . C9 C -0.1262(5) 0.3643(5) 0.07873(8) 0.0710(9) Uani 1 1 d . . . . . H9 H -0.2482 0.4023 0.0858 0.085 Uiso 1 1 calc R U . . . C10 C -0.0676(5) 0.1837(5) 0.09192(9) 0.0698(10) Uani 1 1 d . . . . . H10A H -0.0746 0.1826 0.1171 0.084 Uiso 1 1 calc R U . . . H10B H -0.1488 0.0907 0.0831 0.084 Uiso 1 1 calc R U . . . C11 C 0.0228(6) 0.5003(6) 0.08587(11) 0.0814(11) Uani 1 1 d . . . . . H11A H 0.0936 0.4749 0.1065 0.098 Uiso 1 1 calc R U . . . H11B H -0.0165 0.6260 0.0852 0.098 Uiso 1 1 calc R U . . . C12 C -0.1112(5) 0.2254(6) 0.01717(9) 0.0745(11) Uani 1 1 d . . . . . H12A H -0.2383 0.1972 0.0159 0.112 Uiso 1 1 calc R U . . . H12B H -0.0465 0.1231 0.0265 0.112 Uiso 1 1 calc R U . . . H12C H -0.0661 0.2524 -0.0056 0.112 Uiso 1 1 calc R U . . . C13 C -0.1763(6) 0.5455(6) 0.02440(12) 0.0912(13) Uani 1 1 d . . . . . H13A H -0.1259 0.5691 0.0019 0.137 Uiso 1 1 calc R U . . . H13B H -0.1584 0.6496 0.0390 0.137 Uiso 1 1 calc R U . . . H13C H -0.3039 0.5213 0.0222 0.137 Uiso 1 1 calc R U . . . N1 N 0.4705(4) 0.0857(4) 0.05867(8) 0.0728(9) Uani 1 1 d . . . . . O1 O 0.4296(5) -0.3252(4) 0.09947(10) 0.1086(12) Uani 1 1 d . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.085(3) 0.076(3) 0.090(3) -0.001(2) -0.016(2) 0.010(2) C2 0.065(2) 0.070(2) 0.0631(19) -0.0010(15) -0.0101(17) 0.0002(17) C3 0.066(2) 0.072(2) 0.0605(18) 0.0066(16) -0.0051(16) -0.0056(18) C4 0.0550(17) 0.071(2) 0.0558(16) 0.0017(15) 0.0009(15) -0.0055(16) C5 0.0561(18) 0.068(2) 0.0609(19) 0.0000(16) -0.0004(15) -0.0019(16) C6 0.059(2) 0.078(2) 0.073(2) 0.0073(18) 0.0036(17) -0.0029(18) C7 0.064(2) 0.065(2) 0.080(2) 0.0067(17) 0.0018(18) -0.0019(17) C8 0.062(2) 0.076(2) 0.0655(19) 0.0062(17) 0.0014(15) 0.0055(18) C9 0.0612(19) 0.084(2) 0.0675(19) -0.0047(18) 0.0083(17) 0.0066(18) C10 0.062(2) 0.087(2) 0.0607(18) 0.0053(17) 0.0070(16) -0.0034(18) C11 0.081(3) 0.076(2) 0.087(3) -0.014(2) -0.001(2) 0.0023(19) C12 0.069(2) 0.094(3) 0.0602(19) -0.0023(18) -0.0026(17) 0.001(2) C13 0.082(3) 0.098(3) 0.094(3) 0.020(2) 0.005(2) 0.023(2) N1 0.0619(17) 0.080(2) 0.0764(18) 0.0003(16) 0.0005(15) 0.0053(16) O1 0.110(3) 0.080(2) 0.135(3) 0.0191(19) -0.036(2) 0.0047(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.199(5) . ? C1 C2 1.468(5) . ? C1 H1 0.9500 . ? C2 N1 1.344(5) . ? C2 C3 1.380(5) . ? C3 C4 1.379(5) . ? C3 H3 0.9500 . ? C4 C5 1.404(5) . ? C4 C10 1.506(5) . ? C5 C6 1.386(5) . ? C5 C7 1.486(5) . ? C6 N1 1.329(5) . ? C6 H6 0.9500 . ? C7 C11 1.551(5) . ? C7 C8 1.568(5) . ? C7 H7 1.0000 . ? C8 C12 1.514(6) . ? C8 C13 1.522(5) . ? C8 C9 1.560(5) . ? C9 C10 1.519(5) . ? C9 C11 1.542(6) . ? C9 H9 1.0000 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 125.4(4) . . ? O1 C1 H1 117.3 . . ? C2 C1 H1 117.3 . . ? N1 C2 C3 123.5(3) . . ? N1 C2 C1 114.2(3) . . ? C3 C2 C1 122.3(4) . . ? C4 C3 C2 119.9(3) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C5 117.4(3) . . ? C3 C4 C10 124.8(3) . . ? C5 C4 C10 117.8(3) . . ? C6 C5 C4 118.3(3) . . ? C6 C5 C7 125.0(3) . . ? C4 C5 C7 116.7(3) . . ? N1 C6 C5 124.6(3) . . ? N1 C6 H6 117.7 . . ? C5 C6 H6 117.7 . . ? C5 C7 C11 106.8(3) . . ? C5 C7 C8 110.2(3) . . ? C11 C7 C8 87.3(3) . . ? C5 C7 H7 116.3 . . ? C11 C7 H7 116.3 . . ? C8 C7 H7 116.3 . . ? C12 C8 C13 109.1(3) . . ? C12 C8 C9 118.3(3) . . ? C13 C8 C9 112.4(3) . . ? C12 C8 C7 119.3(3) . . ? C13 C8 C7 111.1(3) . . ? C9 C8 C7 84.9(2) . . ? C10 C9 C11 108.7(3) . . ? C10 C9 C8 111.3(3) . . ? C11 C9 C8 88.0(3) . . ? C10 C9 H9 115.3 . . ? C11 C9 H9 115.3 . . ? C8 C9 H9 115.3 . . ? C4 C10 C9 110.9(3) . . ? C4 C10 H10A 109.5 . . ? C9 C10 H10A 109.5 . . ? C4 C10 H10B 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 108.0 . . ? C9 C11 C7 86.0(3) . . ? C9 C11 H11A 114.3 . . ? C7 C11 H11A 114.3 . . ? C9 C11 H11B 114.3 . . ? C7 C11 H11B 114.3 . . ? H11A C11 H11B 111.5 . . ? C8 C12 H12A 109.5 . . ? C8 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C8 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C8 C13 H13A 109.5 . . ? C8 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C8 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C6 N1 C2 116.4(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 N1 -176.1(4) . . . . ? O1 C1 C2 C3 3.6(6) . . . . ? N1 C2 C3 C4 1.3(5) . . . . ? C1 C2 C3 C4 -178.4(3) . . . . ? C2 C3 C4 C5 -0.3(5) . . . . ? C2 C3 C4 C10 179.5(3) . . . . ? C3 C4 C5 C6 -0.9(5) . . . . ? C10 C4 C5 C6 179.4(3) . . . . ? C3 C4 C5 C7 -179.9(3) . . . . ? C10 C4 C5 C7 0.3(4) . . . . ? C4 C5 C6 N1 1.1(5) . . . . ? C7 C5 C6 N1 -179.9(3) . . . . ? C6 C5 C7 C11 -132.2(4) . . . . ? C4 C5 C7 C11 46.8(4) . . . . ? C6 C5 C7 C8 134.4(4) . . . . ? C4 C5 C7 C8 -46.6(4) . . . . ? C5 C7 C8 C12 -40.1(4) . . . . ? C11 C7 C8 C12 -147.0(3) . . . . ? C5 C7 C8 C13 -168.4(3) . . . . ? C11 C7 C8 C13 84.7(3) . . . . ? C5 C7 C8 C9 79.6(3) . . . . ? C11 C7 C8 C9 -27.3(3) . . . . ? C12 C8 C9 C10 38.9(4) . . . . ? C13 C8 C9 C10 167.5(3) . . . . ? C7 C8 C9 C10 -81.8(3) . . . . ? C12 C8 C9 C11 148.2(3) . . . . ? C13 C8 C9 C11 -83.3(4) . . . . ? C7 C8 C9 C11 27.5(3) . . . . ? C3 C4 C10 C9 179.5(3) . . . . ? C5 C4 C10 C9 -0.8(4) . . . . ? C11 C9 C10 C4 -46.7(4) . . . . ? C8 C9 C10 C4 48.5(4) . . . . ? C10 C9 C11 C7 84.0(3) . . . . ? C8 C9 C11 C7 -27.8(3) . . . . ? C5 C7 C11 C9 -82.7(3) . . . . ? C8 C7 C11 C9 27.6(3) . . . . ? C5 C6 N1 C2 -0.1(5) . . . . ? C3 C2 N1 C6 -1.1(5) . . . . ? C1 C2 N1 C6 178.6(3) . . . . ? _refine_diff_density_max 0.205 _refine_diff_density_min -0.183 _refine_diff_density_rms 0.071 _shelx_res_file ; shelx.res created by SHELXL-2014/7 TITL shelxt_a.res in P1 New: P43212 CELL 0.71073 7.5168 7.5168 39.3160 90.000 90.000 90.000 ZERR 8.00 0.0004 0.0004 0.0020 0.000 0.000 0.000 LATT -1 SYMM 1/2 - Y, 1/2 + X, 3/4 + Z SYMM - X, - Y, 1/2 + Z SYMM 1/2 + Y, 1/2 - X, 1/4 + Z SYMM 1/2 + X, 1/2 - Y, 1/4 - Z SYMM Y, X, - Z SYMM 1/2 - X, 1/2 + Y, 3/4 - Z SYMM - Y, - X, 1/2 - Z SFAC C H N O UNIT 104 120 8 8 MERG 2 TWIN OMIT 0 8 20 OMIT 4 6 27 FMAP 2 PLAN 5 SIZE 0.110 0.120 0.130 ACTA BOND $H CONF L.S. 50 TEMP -73.00 WGHT 0.089200 0.000000 3.000000 0.040000 0.000000 0.100000 EXTI 0.019978 BASF -3.32341 FVAR 0.50237 C1 1 0.484786 -0.197283 0.084648 11.00000 0.08529 0.07550 = 0.08954 -0.00062 -0.01579 0.01015 AFIX 43 H1 2 0.604403 -0.201221 0.076884 11.00000 -1.20000 AFIX 0 C2 1 0.382823 -0.035030 0.077500 11.00000 0.06504 0.06977 = 0.06311 -0.00097 -0.01008 0.00023 C3 1 0.211321 -0.010638 0.089162 11.00000 0.06639 0.07172 = 0.06045 0.00660 -0.00506 -0.00563 AFIX 43 H3 2 0.156304 -0.099286 0.102799 11.00000 -1.20000 AFIX 0 C4 1 0.119990 0.142617 0.080985 11.00000 0.05498 0.07113 = 0.05580 0.00170 0.00092 -0.00551 C5 1 0.208686 0.268891 0.060876 11.00000 0.05606 0.06781 = 0.06087 0.00003 -0.00040 -0.00186 C6 1 0.382012 0.233272 0.050950 11.00000 0.05854 0.07797 = 0.07345 0.00734 0.00356 -0.00287 AFIX 43 H6 2 0.441688 0.320480 0.037695 11.00000 -1.20000 AFIX 0 C7 1 0.108374 0.433300 0.052331 11.00000 0.06428 0.06513 = 0.07962 0.00670 0.00181 -0.00191 AFIX 13 H7 2 0.173408 0.524135 0.038520 11.00000 -1.20000 AFIX 0 C8 1 -0.084172 0.384968 0.040073 11.00000 0.06213 0.07587 = 0.06549 0.00624 0.00143 0.00548 C9 1 -0.126166 0.364348 0.078731 11.00000 0.06121 0.08425 = 0.06754 -0.00469 0.00827 0.00659 AFIX 13 H9 2 -0.248245 0.402310 0.085767 11.00000 -1.20000 AFIX 0 C10 1 -0.067573 0.183685 0.091919 11.00000 0.06156 0.08715 = 0.06071 0.00534 0.00703 -0.00337 AFIX 23 H10A 2 -0.074568 0.182570 0.117063 11.00000 -1.20000 H10B 2 -0.148786 0.090742 0.083131 11.00000 -1.20000 AFIX 0 C11 1 0.022781 0.500339 0.085871 11.00000 0.08078 0.07640 = 0.08705 -0.01425 -0.00057 0.00233 AFIX 23 H11A 2 0.093606 0.474873 0.106535 11.00000 -1.20000 H11B 2 -0.016450 0.626020 0.085225 11.00000 -1.20000 AFIX 0 C12 1 -0.111155 0.225352 0.017173 11.00000 0.06892 0.09435 = 0.06015 -0.00226 -0.00260 0.00094 AFIX 137 H12A 2 -0.238262 0.197169 0.015859 11.00000 -1.50000 H12B 2 -0.046537 0.123099 0.026473 11.00000 -1.50000 H12C 2 -0.066137 0.252450 -0.005639 11.00000 -1.50000 AFIX 0 C13 1 -0.176290 0.545514 0.024405 11.00000 0.08225 0.09791 = 0.09356 0.02019 0.00511 0.02303 AFIX 137 H13A 2 -0.125873 0.569053 0.001863 11.00000 -1.50000 H13B 2 -0.158432 0.649588 0.039025 11.00000 -1.50000 H13C 2 -0.303893 0.521303 0.022236 11.00000 -1.50000 AFIX 0 N1 3 0.470527 0.085728 0.058674 11.00000 0.06191 0.08007 = 0.07639 0.00027 0.00049 0.00525 O1 4 0.429624 -0.325237 0.099470 11.00000 0.11037 0.07988 = 0.13548 0.01914 -0.03632 0.00470 HKLF 4 1.0 0.00 -1.00 0.00 -1.00 0.00 0.00 0.00 0.00 -1.00 REM shelxt_a.res in P1 New: P43212 REM R1 = 0.0507 for 1336 Fo > 4sig(Fo) and 0.0797 for all 1977 data REM 140 parameters refined using 0 restraints END WGHT 0.0868 0.0000 REM Highest difference peak 0.205, deepest hole -0.183, 1-sigma level 0.071 Q1 1 0.6458 0.1380 0.0602 11.00000 0.05 0.21 Q2 1 0.6158 0.1703 0.0634 11.00000 0.05 0.20 Q3 1 -0.3058 0.2834 0.0656 11.00000 0.05 0.19 Q4 1 0.2239 0.0816 0.0532 11.00000 0.05 0.18 Q5 1 0.5876 0.3525 0.0594 11.00000 0.05 0.17 ; _shelx_res_checksum 31704