####################################################################### # # 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_sd21 _database_code_depnum_ccdc_archive 'CCDC 1482859' _audit_update_record ; 2016-09-29 deposited with the CCDC. 2016-10-17 downloaded from the CCDC. ; _audit_creation_method SHELXL-97 _chemical_name_systematic 'oxovanadium {(Z)-2-hydroxy-N-((E)-(2-oxidonaphthalen-1-yl)methylene)benzohydrazonate}ethanoate' _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H17 N2 O5 V' _chemical_formula_sum 'C20 H17 N2 O5 V' _chemical_formula_weight 416.30 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' V V 0.3005 0.5294 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 21/c' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 18.249(3) _cell_length_b 5.9376(11) _cell_length_c 18.227(3) _cell_angle_alpha 90.00 _cell_angle_beta 110.346(9) _cell_angle_gamma 90.00 _cell_volume 1851.8(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4558 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 25.40 _exptl_crystal_description 'rectangular plate' _exptl_crystal_colour brown _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.493 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 0.571 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8658 _exptl_absorpt_correction_T_max 0.9887 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 0.3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26070 _diffrn_reflns_av_R_equivalents 0.0979 _diffrn_reflns_av_unetl/netl 0.0717 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3645 _reflns_number_gt 2288 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ORTEP-III _computing_publication_material WinGXv1.80.05 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1267P)^2^+4.0517P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3645 _refine_ls_number_parameters 246 _refine_ls_number_restraints 13 _refine_ls_R_factor_all 0.1296 _refine_ls_R_factor_gt 0.0831 _refine_ls_wR_factor_ref 0.2560 _refine_ls_wR_factor_gt 0.2028 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.063 _refine_ls_shift/su_max 0.005 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group V1 V 0.34248(6) 0.29248(17) 0.48670(5) 0.0435(4) Uani 1 1 d . . . O1 O 0.2944(2) 0.0422(6) 0.4312(2) 0.0443(9) Uani 1 1 d . . . O2 O 0.3371(2) 0.5156(7) 0.5621(2) 0.0483(10) Uani 1 1 d . . . O5 O 0.1475(3) 0.9677(9) 0.5096(3) 0.0589(13) Uani 1 1 d . . . O3 O 0.3763(3) 0.4250(8) 0.4303(3) 0.0621(12) Uani 1 1 d . . . O4 O 0.4190(3) 0.1593(10) 0.5577(3) 0.0822(12) Uani 1 1 d . . . N1 N 0.2279(3) 0.4164(7) 0.4436(2) 0.0383(10) Uani 1 1 d . . . N2 N 0.2119(3) 0.5967(8) 0.4840(2) 0.0401(11) Uani 1 1 d . . . C1 C 0.2371(3) 0.0155(9) 0.3615(3) 0.0395(12) Uani 1 1 d . . . C2 C 0.2392(4) -0.1817(9) 0.3189(3) 0.0448(14) Uani 1 1 d . . . H2 H 0.2792 -0.2860 0.3392 0.054 Uiso 1 1 calc R . . C3 C 0.1828(4) -0.2184(9) 0.2484(3) 0.0461(14) Uani 1 1 d . . . H3 H 0.1845 -0.3498 0.2212 0.055 Uiso 1 1 calc R . . C4 C 0.1211(3) -0.0627(9) 0.2145(3) 0.0429(13) Uani 1 1 d . . . C5 C 0.0653(4) -0.0967(11) 0.1397(3) 0.0508(15) Uani 1 1 d . . . H5 H 0.0675 -0.2270 0.1122 0.061 Uiso 1 1 calc R . . C6 C 0.0083(4) 0.0564(12) 0.1066(3) 0.0529(16) Uani 1 1 d . . . H6 H -0.0279 0.0319 0.0568 0.063 Uiso 1 1 calc R . . C7 C 0.0042(4) 0.2518(11) 0.1481(3) 0.0523(15) Uani 1 1 d . . . H7 H -0.0344 0.3581 0.1253 0.063 Uiso 1 1 calc R . . C8 C 0.0567(3) 0.2879(10) 0.2221(3) 0.0453(13) Uani 1 1 d . . . H8 H 0.0521 0.4164 0.2493 0.054 Uiso 1 1 calc R . . C9 C 0.1176(3) 0.1343(9) 0.2575(3) 0.0369(12) Uani 1 1 d . . . C10 C 0.1762(3) 0.1691(9) 0.3336(3) 0.0364(12) Uani 1 1 d . . . C11 C 0.1723(3) 0.3540(9) 0.3805(3) 0.0372(12) Uani 1 1 d . . . H11 H 0.1263 0.4377 0.3650 0.045 Uiso 1 1 calc R . . C12 C 0.2742(3) 0.6411(9) 0.5441(3) 0.0417(13) Uani 1 1 d . . . C13 C 0.2744(3) 0.8327(9) 0.5953(3) 0.0396(13) Uani 1 1 d . . . C14 C 0.2118(3) 0.9886(10) 0.5745(3) 0.0441(13) Uani 1 1 d . . . C15 C 0.2153(4) 1.1723(10) 0.6217(3) 0.0517(15) Uani 1 1 d . . . H15 H 0.1747 1.2764 0.6078 0.062 Uiso 1 1 calc R . . C16 C 0.2785(4) 1.2030(11) 0.6892(4) 0.0590(17) Uani 1 1 d . . . H16 H 0.2803 1.3284 0.7203 0.071 Uiso 1 1 calc R . . C17 C 0.3389(4) 1.0508(12) 0.7113(4) 0.0594(17) Uani 1 1 d . . . H17 H 0.3810 1.0723 0.7574 0.071 Uiso 1 1 calc R . . C18 C 0.3369(4) 0.8653(11) 0.6646(3) 0.0516(15) Uani 1 1 d . . . H18 H 0.3777 0.7618 0.6797 0.062 Uiso 1 1 calc R . . C19 C 0.4980(4) 0.1932(13) 0.5950(5) 0.0822(12) Uani 1 1 d DU . . H19A H 0.5056 0.3338 0.6238 0.099 Uiso 1 1 calc R . . H19B H 0.5225 0.2083 0.5558 0.099 Uiso 1 1 calc R . . C20 C 0.5376(4) 0.0106(14) 0.6497(4) 0.0822(12) Uani 1 1 d DU . . H20A H 0.5128 -0.0090 0.6878 0.123 Uiso 1 1 calc R . . H20B H 0.5915 0.0494 0.6757 0.123 Uiso 1 1 calc R . . H20C H 0.5343 -0.1270 0.6211 0.123 Uiso 1 1 calc R . . H5A H 0.150(4) 0.872(13) 0.485(4) 0.07(3) Uiso 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 V1 0.0521(6) 0.0438(6) 0.0355(6) 0.0041(4) 0.0165(4) 0.0035(4) O1 0.059(2) 0.041(2) 0.0336(19) 0.0043(16) 0.0160(18) 0.0080(18) O2 0.055(2) 0.053(2) 0.034(2) -0.0058(17) 0.0118(18) 0.0032(19) O5 0.073(3) 0.058(3) 0.043(3) -0.009(2) 0.017(2) 0.006(2) O3 0.073(3) 0.060(3) 0.066(3) 0.010(2) 0.040(2) -0.004(2) O4 0.069(2) 0.090(3) 0.075(2) 0.013(2) 0.0091(18) 0.010(2) N1 0.057(3) 0.033(2) 0.027(2) -0.0010(18) 0.017(2) -0.001(2) N2 0.052(3) 0.039(3) 0.030(2) -0.0050(19) 0.016(2) -0.001(2) C1 0.055(3) 0.034(3) 0.035(3) 0.004(2) 0.023(3) -0.001(2) C2 0.063(4) 0.035(3) 0.042(3) 0.008(2) 0.025(3) 0.010(3) C3 0.074(4) 0.031(3) 0.045(3) -0.003(2) 0.034(3) -0.002(3) C4 0.060(4) 0.041(3) 0.035(3) -0.004(2) 0.026(3) -0.008(3) C5 0.071(4) 0.053(4) 0.035(3) -0.015(3) 0.026(3) -0.011(3) C6 0.053(4) 0.075(5) 0.031(3) -0.009(3) 0.015(3) -0.008(3) C7 0.051(4) 0.063(4) 0.039(3) -0.001(3) 0.011(3) 0.004(3) C8 0.054(3) 0.049(3) 0.034(3) -0.003(2) 0.016(3) 0.001(3) C9 0.048(3) 0.037(3) 0.029(3) -0.001(2) 0.017(2) -0.003(2) C10 0.051(3) 0.033(3) 0.032(3) 0.003(2) 0.022(2) 0.001(2) C11 0.045(3) 0.039(3) 0.029(3) 0.000(2) 0.014(2) 0.000(2) C12 0.057(4) 0.041(3) 0.030(3) 0.003(2) 0.019(3) -0.006(3) C13 0.057(3) 0.038(3) 0.028(3) -0.002(2) 0.021(2) -0.006(2) C14 0.059(4) 0.048(3) 0.029(3) 0.003(2) 0.021(3) -0.002(3) C15 0.074(4) 0.045(4) 0.044(3) -0.001(3) 0.031(3) -0.004(3) C16 0.090(5) 0.050(4) 0.048(4) -0.018(3) 0.038(4) -0.017(4) C17 0.072(4) 0.068(5) 0.036(3) -0.013(3) 0.016(3) -0.016(4) C18 0.059(4) 0.059(4) 0.036(3) -0.008(3) 0.016(3) -0.005(3) C19 0.069(2) 0.090(3) 0.075(2) 0.013(2) 0.0091(18) 0.010(2) C20 0.069(2) 0.090(3) 0.075(2) 0.013(2) 0.0091(18) 0.010(2) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 V1 O3 1.579(4) . ? V1 O4 1.731(5) . ? V1 O1 1.840(4) . ? V1 O2 1.936(4) . ? V1 N1 2.096(5) . ? O1 C1 1.345(6) . ? O2 C12 1.312(7) . ? O5 C14 1.352(7) . ? O5 H5A 0.74(7) . ? O4 C19 1.378(9) . ? N1 C11 1.296(6) . ? N1 N2 1.385(6) . ? N2 C12 1.302(7) . ? C1 C10 1.390(7) . ? C1 C2 1.413(7) . ? C2 C3 1.357(8) . ? C2 H2 0.9300 . ? C3 C4 1.421(8) . ? C3 H3 0.9300 . ? C4 C5 1.405(8) . ? C4 C9 1.422(7) . ? C5 C6 1.355(9) . ? C5 H5 0.9300 . ? C6 C7 1.401(9) . ? C6 H6 0.9300 . ? C7 C8 1.372(8) . ? C7 H7 0.9300 . ? C8 C9 1.409(8) . ? C8 H8 0.9300 . ? C9 C10 1.442(7) . ? C10 C11 1.408(7) . ? C11 H11 0.9300 . ? C12 C13 1.471(7) . ? C13 C18 1.391(8) . ? C13 C14 1.415(8) . ? C14 C15 1.377(8) . ? C15 C16 1.374(9) . ? C15 H15 0.9300 . ? C16 C17 1.373(10) . ? C16 H16 0.9300 . ? C17 C18 1.385(9) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 C20 1.480(7) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? 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 O3 V1 O4 108.6(3) . . ? O3 V1 O1 105.3(2) . . ? O4 V1 O1 98.6(2) . . ? O3 V1 O2 104.4(2) . . ? O4 V1 O2 90.5(2) . . ? O1 V1 O2 144.20(18) . . ? O3 V1 N1 98.4(2) . . ? O4 V1 N1 151.8(2) . . ? O1 V1 N1 81.65(17) . . ? O2 V1 N1 74.66(16) . . ? C1 O1 V1 132.8(3) . . ? C12 O2 V1 117.8(3) . . ? C14 O5 H5A 113(6) . . ? C19 O4 V1 137.4(5) . . ? C11 N1 N2 116.6(4) . . ? C11 N1 V1 127.1(4) . . ? N2 N1 V1 116.0(3) . . ? C12 N2 N1 108.7(4) . . ? O1 C1 C10 121.9(5) . . ? O1 C1 C2 117.1(5) . . ? C10 C1 C2 120.9(5) . . ? C3 C2 C1 119.8(5) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C2 C3 C4 122.2(5) . . ? C2 C3 H3 118.9 . . ? C4 C3 H3 118.9 . . ? C5 C4 C3 121.7(5) . . ? C5 C4 C9 119.8(5) . . ? C3 C4 C9 118.5(5) . . ? C6 C5 C4 121.4(6) . . ? C6 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? C5 C6 C7 119.5(5) . . ? C5 C6 H6 120.3 . . ? C7 C6 H6 120.3 . . ? C8 C7 C6 120.7(6) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C7 C8 C9 121.3(6) . . ? C7 C8 H8 119.4 . . ? C9 C8 H8 119.4 . . ? C8 C9 C4 117.3(5) . . ? C8 C9 C10 123.5(5) . . ? C4 C9 C10 119.2(5) . . ? C1 C10 C11 119.5(5) . . ? C1 C10 C9 119.3(5) . . ? C11 C10 C9 121.2(5) . . ? N1 C11 C10 124.9(5) . . ? N1 C11 H11 117.5 . . ? C10 C11 H11 117.5 . . ? N2 C12 O2 121.8(5) . . ? N2 C12 C13 120.0(5) . . ? O2 C12 C13 118.2(5) . . ? C18 C13 C14 118.9(5) . . ? C18 C13 C12 120.3(5) . . ? C14 C13 C12 120.8(5) . . ? O5 C14 C15 117.2(6) . . ? O5 C14 C13 123.3(5) . . ? C15 C14 C13 119.5(5) . . ? C16 C15 C14 120.4(6) . . ? C16 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C17 C16 C15 120.9(6) . . ? C17 C16 H16 119.6 . . ? C15 C16 H16 119.6 . . ? C16 C17 C18 119.8(6) . . ? C16 C17 H17 120.1 . . ? C18 C17 H17 120.1 . . ? C17 C18 C13 120.4(6) . . ? C17 C18 H18 119.8 . . ? C13 C18 H18 119.8 . . ? O4 C19 C20 114.0(7) . . ? O4 C19 H19A 108.7 . . ? C20 C19 H19A 108.7 . . ? O4 C19 H19B 108.7 . . ? C20 C19 H19B 108.7 . . ? H19A C19 H19B 107.6 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? 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 O3 V1 O1 C1 -57.1(5) . . . . ? O4 V1 O1 C1 -169.1(5) . . . . ? O2 V1 O1 C1 88.0(5) . . . . ? N1 V1 O1 C1 39.4(4) . . . . ? O3 V1 O2 C12 86.3(4) . . . . ? O4 V1 O2 C12 -164.4(4) . . . . ? O1 V1 O2 C12 -59.0(5) . . . . ? N1 V1 O2 C12 -8.6(4) . . . . ? O3 V1 O4 C19 28.5(9) . . . . ? O1 V1 O4 C19 137.9(8) . . . . ? O2 V1 O4 C19 -76.9(8) . . . . ? N1 V1 O4 C19 -133.8(8) . . . . ? O3 V1 N1 C11 78.2(5) . . . . ? O4 V1 N1 C11 -118.7(6) . . . . ? O1 V1 N1 C11 -26.2(4) . . . . ? O2 V1 N1 C11 -179.1(5) . . . . ? O3 V1 N1 N2 -96.3(4) . . . . ? O4 V1 N1 N2 66.8(6) . . . . ? O1 V1 N1 N2 159.3(4) . . . . ? O2 V1 N1 N2 6.4(3) . . . . ? C11 N1 N2 C12 -178.2(4) . . . . ? V1 N1 N2 C12 -3.1(5) . . . . ? V1 O1 C1 C10 -33.3(7) . . . . ? V1 O1 C1 C2 149.6(4) . . . . ? O1 C1 C2 C3 179.7(5) . . . . ? C10 C1 C2 C3 2.5(8) . . . . ? C1 C2 C3 C4 0.8(8) . . . . ? C2 C3 C4 C5 176.6(5) . . . . ? C2 C3 C4 C9 -1.9(8) . . . . ? C3 C4 C5 C6 -177.6(6) . . . . ? C9 C4 C5 C6 0.9(9) . . . . ? C4 C5 C6 C7 -0.7(9) . . . . ? C5 C6 C7 C8 -0.8(9) . . . . ? C6 C7 C8 C9 2.0(9) . . . . ? C7 C8 C9 C4 -1.7(8) . . . . ? C7 C8 C9 C10 177.3(5) . . . . ? C5 C4 C9 C8 0.3(8) . . . . ? C3 C4 C9 C8 178.8(5) . . . . ? C5 C4 C9 C10 -178.8(5) . . . . ? C3 C4 C9 C10 -0.2(7) . . . . ? O1 C1 C10 C11 -2.3(8) . . . . ? C2 C1 C10 C11 174.7(5) . . . . ? O1 C1 C10 C9 178.3(5) . . . . ? C2 C1 C10 C9 -4.6(8) . . . . ? C8 C9 C10 C1 -175.6(5) . . . . ? C4 C9 C10 C1 3.4(7) . . . . ? C8 C9 C10 C11 5.1(8) . . . . ? C4 C9 C10 C11 -175.9(5) . . . . ? N2 N1 C11 C10 -177.1(5) . . . . ? V1 N1 C11 C10 8.4(8) . . . . ? C1 C10 C11 N1 11.7(8) . . . . ? C9 C10 C11 N1 -169.0(5) . . . . ? N1 N2 C12 O2 -4.4(7) . . . . ? N1 N2 C12 C13 177.2(4) . . . . ? V1 O2 C12 N2 10.7(7) . . . . ? V1 O2 C12 C13 -171.0(3) . . . . ? N2 C12 C13 C18 172.3(5) . . . . ? O2 C12 C13 C18 -6.0(8) . . . . ? N2 C12 C13 C14 -8.6(8) . . . . ? O2 C12 C13 C14 173.0(5) . . . . ? C18 C13 C14 O5 -178.0(5) . . . . ? C12 C13 C14 O5 3.0(8) . . . . ? C18 C13 C14 C15 2.1(8) . . . . ? C12 C13 C14 C15 -176.9(5) . . . . ? O5 C14 C15 C16 179.1(5) . . . . ? C13 C14 C15 C16 -1.0(9) . . . . ? C14 C15 C16 C17 -0.5(9) . . . . ? C15 C16 C17 C18 0.8(10) . . . . ? C16 C17 C18 C13 0.3(10) . . . . ? C14 C13 C18 C17 -1.8(8) . . . . ? C12 C13 C18 C17 177.2(5) . . . . ? V1 O4 C19 C20 -176.2(6) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.509 _refine_diff_density_min -1.150 _refine_diff_density_rms 0.112 ####################################################################### # # 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_SPD-65 _database_code_depnum_ccdc_archive 'CCDC 1482860' _audit_update_record ; 2016-05-31 deposited with the CCDC. 2016-10-17 downloaded from the CCDC. ; _audit_creation_method SHELXL-2013 _chemical_name_systematic ; bis[oxovadnadium (Z)-2-hydroxy-N-((E)-(2-oxidonaphthalen-1-yl)methylene)benzohydrazonate ethanoate] 4,4'-bipyridine ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(C10 H8 N2){(C18 H12 N2 O3)(C2 H5 O)O V}2' _chemical_formula_sum 'C50 H42 N6 O10 V2' _chemical_formula_weight 988.77 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' V V 0.0687 2.1097 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system tetragonal _space_group_IT_number 85 _space_group_name_H-M_alt 'P 4/n' _space_group_name_Hall '-P 4a' _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, z' '-x+1/2, -y+1/2, z' 'y, -x+1/2, z' '-x, -y, -z' 'y-1/2, -x, -z' 'x-1/2, y-1/2, -z' '-y, x-1/2, -z' _cell_length_a 21.5608(3) _cell_length_b 21.5608(3) _cell_length_c 10.1344(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 4711.16(19) _cell_formula_units_Z 4 _cell_measurement_reflns_used 6418 _cell_measurement_temperature 99.9(3) _cell_measurement_theta_max 66.4769 _cell_measurement_theta_min 11.0923 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.394 _exptl_crystal_F_000 2040 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_description square _exptl_crystal_colour 'reddish black' _exptl_crystal_size_max 0.1409 _exptl_crystal_size_mid 0.1037 _exptl_crystal_size_min 0.0504 _exptl_absorpt_coefficient_mu 3.872 _shelx_estimated_absorpt_T_min ? _shelx_estimated_absorpt_T_max ? _exptl_absorpt_correction_T_max 1.178 _exptl_absorpt_correction_T_min 0.894 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.18t (release 05-06-2012 CrysAlis171 .NET) (compiled Jun 5 2012,17:40:27) Numerical absorption correction based on gaussian integration over a multifaceted crystal model ; _exptl_special_details ; ? ; _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega 9.00 37.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - -54.6574 -19.0000 -150.0000 28 #__ type_ start__ end____ width___ exp.time_ 2 omega -147.00 -71.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - -54.6574 -19.0000 -150.0000 76 #__ type_ start__ end____ width___ exp.time_ 3 omega 101.00 147.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 54.6574 111.0000 -35.0000 46 #__ type_ start__ end____ width___ exp.time_ 4 omega 104.00 169.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 109.3147 111.0000 0.0000 65 #__ type_ start__ end____ width___ exp.time_ 5 omega 100.00 177.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 109.3147 111.0000 -35.0000 77 #__ type_ start__ end____ width___ exp.time_ 6 omega 18.00 93.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 109.3147 -25.0000 -90.0000 75 #__ type_ start__ end____ width___ exp.time_ 7 omega 53.00 88.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 109.3147 -25.0000 -150.0000 35 #__ type_ start__ end____ width___ exp.time_ 8 omega -150.00 -79.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - -54.6574 -99.0000 -30.0000 71 #__ type_ start__ end____ width___ exp.time_ 9 omega 10.00 157.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 54.6574 77.0000 60.0000 147 #__ type_ start__ end____ width___ exp.time_ 10 omega 57.00 123.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 109.3147 178.0000 150.0000 66 ; _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0614722000 _diffrn_orient_matrix_UB_12 0.0093109000 _diffrn_orient_matrix_UB_13 0.0749318000 _diffrn_orient_matrix_UB_21 0.0153250000 _diffrn_orient_matrix_UB_22 -0.0692893000 _diffrn_orient_matrix_UB_23 -0.0178411000 _diffrn_orient_matrix_UB_31 0.0330641000 _diffrn_orient_matrix_UB_32 0.0148702000 _diffrn_orient_matrix_UB_33 -0.1309686000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.5418 _diffrn_source 'SuperNova (Cu) X-ray Source' _reflns_odcompleteness_completeness 98.63 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.49 _diffrn_ambient_temperature 99.9(2) _diffrn_reflns_number 12631 _diffrn_reflns_av_unetI/netI 0.0278 _diffrn_reflns_av_R_equivalents 0.0317 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 11.203 _diffrn_reflns_theta_max 66.586 _diffrn_reflns_theta_full 67.684 _diffrn_measured_fraction_theta_max 0.987 _diffrn_measured_fraction_theta_full 0.966 _diffrn_reflns_Laue_measured_fraction_max 0.987 _diffrn_reflns_Laue_measured_fraction_full 0.966 _diffrn_reflns_point_group_measured_fraction_max 0.987 _diffrn_reflns_point_group_measured_fraction_full 0.966 _reflns_number_total 4129 _reflns_number_gt 3576 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _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_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.18t (release 05-06-2012 CrysAlis171 .NET) (compiled Jun 5 2012,17:40:27) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.18t (release 05-06-2012 CrysAlis171 .NET) (compiled Jun 5 2012,17:40:27) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.18t (release 05-06-2012 CrysAlis171 .NET) (compiled Jun 5 2012,17:40:27) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _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^)+(0.0629P)^2^+1.3614P] 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 none _refine_ls_extinction_coef . _refine_ls_number_reflns 4129 _refine_ls_number_parameters 381 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0452 _refine_ls_R_factor_gt 0.0377 _refine_ls_wR_factor_ref 0.1054 _refine_ls_wR_factor_gt 0.0994 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.001 _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 V1 V 0.50775(2) 0.37868(2) 0.32114(3) 0.02591(13) Uani 1 1 d . . . . . O3 O 0.44205(7) 0.41279(7) 0.33359(14) 0.0344(3) Uani 1 1 d . . . . . O1 O 0.54488(6) 0.42546(6) 0.18963(13) 0.0279(3) Uani 1 1 d . . . . . O2 O 0.50814(6) 0.33906(6) 0.49591(13) 0.0287(3) Uani 1 1 d . . . . . O4 O 0.48703(6) 0.30754(7) 0.24398(14) 0.0318(3) Uani 1 1 d D . . . . O5 O 0.61222(10) 0.41458(8) 0.80915(16) 0.0471(4) Uani 1 1 d . . . . . N2 N 0.56761(8) 0.41931(8) 0.57240(16) 0.0292(4) Uani 1 1 d . . . . . N1 N 0.55780(7) 0.43992(8) 0.44383(16) 0.0268(4) Uani 1 1 d . . . . . N3 N 0.60584(8) 0.32833(8) 0.32069(16) 0.0262(4) Uani 1 1 d . . . . . C22 C 0.66524(9) 0.23583(9) 0.3547(2) 0.0268(4) Uani 1 1 d . . . . . C12 C 0.53969(9) 0.36580(9) 0.5892(2) 0.0277(4) Uani 1 1 d . . . . . C21 C 0.61024(9) 0.26852(9) 0.3543(2) 0.0280(4) Uani 1 1 d . . . . . C25 C 0.65858(9) 0.35730(9) 0.2863(2) 0.0265(4) Uani 1 1 d . . . . . C1 C 0.56421(9) 0.48384(9) 0.1769(2) 0.0279(4) Uani 1 1 d . . . . . C24 C 0.71564(9) 0.32846(9) 0.2842(2) 0.0262(4) Uani 1 1 d . . . . . C10 C 0.58102(9) 0.52018(9) 0.2853(2) 0.0275(4) Uani 1 1 d . . . . . C9 C 0.60287(9) 0.58302(9) 0.2641(2) 0.0293(4) Uani 1 1 d . . . . . C11 C 0.58136(9) 0.49370(9) 0.4156(2) 0.0278(4) Uani 1 1 d . . . . . C2 C 0.57044(9) 0.50687(10) 0.0466(2) 0.0320(5) Uani 1 1 d . . . . . C23 C 0.71984(9) 0.26631(9) 0.31935(18) 0.0245(4) Uani 1 1 d . . . . . C18 C 0.51549(9) 0.27761(10) 0.7388(2) 0.0333(5) Uani 1 1 d . . . . . C4 C 0.60624(9) 0.60587(10) 0.1326(2) 0.0331(5) Uani 1 1 d . . . . . C8 C 0.61995(10) 0.62337(10) 0.3677(2) 0.0336(5) Uani 1 1 d . . . . . C3 C 0.59022(10) 0.56606(11) 0.0264(2) 0.0350(5) Uani 1 1 d . . . . . C13 C 0.54520(10) 0.33472(10) 0.7185(2) 0.0312(4) Uani 1 1 d . . . . . C17 C 0.52060(11) 0.24678(11) 0.8577(2) 0.0382(5) Uani 1 1 d . . . . . C7 C 0.63858(11) 0.68330(11) 0.3426(3) 0.0392(5) Uani 1 1 d . . . . . C5 C 0.62558(10) 0.66778(11) 0.1107(3) 0.0391(5) Uani 1 1 d . . . . . C14 C 0.58091(12) 0.36024(10) 0.8209(2) 0.0364(5) Uani 1 1 d . . . . . C6 C 0.64102(11) 0.70569(11) 0.2128(3) 0.0424(6) Uani 1 1 d . . . . . C15 C 0.58593(13) 0.32838(12) 0.9407(2) 0.0444(6) Uani 1 1 d . . . . . C19B C 0.4304(2) 0.2749(3) 0.2261(8) 0.0400(12) Uani 0.78(2) 1 d D . P A 1 H19C H 0.4274 0.2603 0.1358 0.048 Uiso 0.78(2) 1 calc R U P A 1 H19D H 0.3957 0.3024 0.2430 0.048 Uiso 0.78(2) 1 calc R U P A 1 C16 C 0.55596(12) 0.27244(12) 0.9587(2) 0.0427(6) Uani 1 1 d . . . . . C20B C 0.42828(18) 0.22068(17) 0.3198(4) 0.0554(9) Uani 0.770(5) 1 d D . P A 1 H20E H 0.4608 0.1921 0.2982 0.083 Uiso 0.770(5) 1 calc R U P A 1 H20F H 0.3889 0.2002 0.3122 0.083 Uiso 0.770(5) 1 calc R U P A 1 H20D H 0.4338 0.2352 0.4085 0.083 Uiso 0.770(5) 1 calc R U P A 1 C20A C 0.4237(6) 0.2195(5) 0.1967(13) 0.0554(9) Uani 0.230(5) 1 d D . P A 2 H20A H 0.4244 0.2278 0.1037 0.083 Uiso 0.230(5) 1 calc R U P A 2 H20B H 0.3856 0.1989 0.2192 0.083 Uiso 0.230(5) 1 calc R U P A 2 H20C H 0.4581 0.1935 0.2196 0.083 Uiso 0.230(5) 1 calc R U P A 2 C19A C 0.4281(6) 0.2798(7) 0.272(2) 0.0400(12) Uani 0.22(2) 1 d D . P A 2 H19B H 0.3949 0.3075 0.2450 0.048 Uiso 0.22(2) 1 calc R U P A 2 H19A H 0.4241 0.2721 0.3657 0.048 Uiso 0.22(2) 1 calc R U P A 2 H8 H 0.6165(10) 0.6113(10) 0.457(2) 0.028(6) Uiso 1 1 d . . . . . H18 H 0.4924(12) 0.2582(12) 0.662(3) 0.041(7) Uiso 1 1 d . . . . . H5 H 0.6265(11) 0.6797(11) 0.021(3) 0.036(6) Uiso 1 1 d . . . . . H3 H 0.5949(10) 0.5813(10) -0.060(2) 0.032(6) Uiso 1 1 d . . . . . H11 H 0.6013(11) 0.5156(11) 0.486(2) 0.038(6) Uiso 1 1 d . . . . . H25 H 0.6557(10) 0.3988(11) 0.263(2) 0.033(6) Uiso 1 1 d . . . . . H2 H 0.5606(11) 0.4792(11) -0.025(3) 0.037(6) Uiso 1 1 d . . . . . H21 H 0.5722(11) 0.2480(10) 0.373(2) 0.031(6) Uiso 1 1 d . . . . . H16 H 0.5598(12) 0.2513(12) 1.041(3) 0.047(7) Uiso 1 1 d . . . . . H24 H 0.7510(10) 0.3518(10) 0.252(2) 0.025(5) Uiso 1 1 d . . . . . H22 H 0.6655(10) 0.1940(11) 0.382(2) 0.031(6) Uiso 1 1 d . . . . . H7 H 0.6493(12) 0.7108(12) 0.419(3) 0.046(7) Uiso 1 1 d . . . . . H17 H 0.5015(12) 0.2083(13) 0.870(3) 0.046(7) Uiso 1 1 d . . . . . H15 H 0.6115(14) 0.3469(14) 1.010(3) 0.060(8) Uiso 1 1 d . . . . . H6 H 0.6529(14) 0.7466(13) 0.192(3) 0.054(8) Uiso 1 1 d . . . . . H5O H 0.6061(16) 0.4289(16) 0.728(4) 0.082(11) Uiso 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 V1 0.0240(2) 0.0294(2) 0.0243(2) -0.00009(13) 0.00057(12) 0.00399(12) O3 0.0309(8) 0.0413(8) 0.0311(8) 0.0013(6) -0.0004(6) 0.0068(6) O1 0.0298(7) 0.0292(7) 0.0248(7) 0.0000(5) 0.0001(5) 0.0033(5) O2 0.0270(7) 0.0334(8) 0.0255(7) 0.0016(6) 0.0029(5) 0.0033(5) O4 0.0308(7) 0.0329(8) 0.0318(8) -0.0008(6) -0.0021(6) -0.0013(6) O5 0.0788(13) 0.0346(9) 0.0279(9) -0.0029(7) -0.0075(8) -0.0020(8) N2 0.0358(9) 0.0286(8) 0.0232(8) -0.0005(7) 0.0009(7) 0.0045(7) N1 0.0294(8) 0.0290(8) 0.0221(8) -0.0010(6) 0.0012(6) 0.0080(6) N3 0.0272(8) 0.0259(8) 0.0255(9) 0.0000(6) 0.0020(6) 0.0020(6) C22 0.0291(10) 0.0230(10) 0.0282(10) 0.0020(8) 0.0012(8) 0.0013(7) C12 0.0259(9) 0.0315(10) 0.0257(10) -0.0017(8) 0.0039(8) 0.0084(7) C21 0.0264(10) 0.0275(10) 0.0299(10) 0.0005(8) 0.0023(8) -0.0005(8) C25 0.0300(10) 0.0231(10) 0.0263(10) 0.0013(8) 0.0005(8) 0.0027(7) C1 0.0219(9) 0.0307(10) 0.0311(11) 0.0033(8) 0.0007(8) 0.0062(7) C24 0.0262(10) 0.0266(10) 0.0257(10) 0.0007(8) 0.0003(8) -0.0008(7) C10 0.0222(9) 0.0314(10) 0.0288(10) 0.0004(8) 0.0019(8) 0.0083(7) C9 0.0217(9) 0.0306(10) 0.0355(11) 0.0016(8) 0.0027(8) 0.0074(7) C11 0.0274(10) 0.0280(10) 0.0280(10) -0.0040(8) 0.0013(8) 0.0074(7) C2 0.0266(10) 0.0407(12) 0.0288(11) 0.0027(9) -0.0008(8) 0.0048(8) C23 0.0260(10) 0.0266(10) 0.0208(9) -0.0017(7) 0.0001(7) 0.0016(8) C18 0.0264(10) 0.0407(12) 0.0327(12) 0.0025(9) 0.0070(8) 0.0073(8) C4 0.0233(10) 0.0363(11) 0.0397(12) 0.0073(9) 0.0012(8) 0.0052(8) C8 0.0287(10) 0.0328(11) 0.0392(12) 0.0011(9) 0.0068(9) 0.0057(8) C3 0.0294(11) 0.0438(12) 0.0319(11) 0.0120(10) -0.0007(9) 0.0049(9) C13 0.0342(11) 0.0339(11) 0.0255(10) 0.0006(8) 0.0053(8) 0.0108(8) C17 0.0379(12) 0.0412(13) 0.0354(12) 0.0076(10) 0.0123(10) 0.0082(9) C7 0.0326(11) 0.0347(12) 0.0503(14) -0.0021(10) 0.0074(10) 0.0018(9) C5 0.0328(11) 0.0389(12) 0.0456(14) 0.0133(10) 0.0034(10) 0.0040(9) C14 0.0508(14) 0.0325(11) 0.0260(11) -0.0031(8) 0.0048(9) 0.0086(9) C6 0.0340(12) 0.0321(12) 0.0611(16) 0.0049(11) 0.0073(11) 0.0004(9) C15 0.0660(16) 0.0433(13) 0.0238(11) -0.0042(9) -0.0003(11) 0.0113(11) C19B 0.0353(13) 0.0377(15) 0.047(3) 0.000(2) -0.0117(19) -0.0063(11) C16 0.0583(15) 0.0452(13) 0.0245(11) 0.0050(10) 0.0096(10) 0.0144(11) C20B 0.055(2) 0.0473(19) 0.064(2) 0.0137(16) -0.0089(17) -0.0173(15) C20A 0.055(2) 0.0473(19) 0.064(2) 0.0137(16) -0.0089(17) -0.0173(15) C19A 0.0353(13) 0.0377(15) 0.047(3) 0.000(2) -0.0117(19) -0.0063(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 V1 O3 1.6010(15) . ? V1 O4 1.7789(14) . ? V1 O1 1.8532(14) . ? V1 O2 1.9664(14) . ? V1 N1 2.1103(17) . ? V1 N3 2.3772(16) . ? O1 C1 1.332(2) . ? O2 C12 1.300(2) . ? O4 C19B 1.420(3) . ? O4 C19A 1.433(9) . ? O5 C14 1.357(3) . ? O5 H5O 0.89(4) . ? N2 C12 1.312(3) . ? N2 N1 1.393(2) . ? N1 C11 1.298(3) . ? N3 C21 1.337(3) . ? N3 C25 1.343(3) . ? C22 C21 1.380(3) . ? C22 C23 1.395(3) . ? C22 H22 0.94(2) . ? C12 C13 1.476(3) . ? C21 H21 0.95(2) . ? C25 C24 1.379(3) . ? C25 H25 0.93(2) . ? C1 C10 1.397(3) . ? C1 C2 1.417(3) . ? C24 C23 1.390(3) . ? C24 H24 0.97(2) . ? C10 C11 1.439(3) . ? C10 C9 1.450(3) . ? C9 C8 1.412(3) . ? C9 C4 1.423(3) . ? C11 H11 0.96(3) . ? C2 C3 1.361(3) . ? C2 H2 0.96(3) . ? C23 C23 1.478(4) 3_655 ? C18 C17 1.381(3) . ? C18 C13 1.403(3) . ? C18 H18 1.01(3) . ? C4 C5 1.416(3) . ? C4 C3 1.419(3) . ? C8 C7 1.377(3) . ? C8 H8 0.95(2) . ? C3 H3 0.94(2) . ? C13 C14 1.405(3) . ? C17 C16 1.391(4) . ? C17 H17 0.93(3) . ? C7 C6 1.402(4) . ? C7 H7 1.00(3) . ? C5 C6 1.359(4) . ? C5 H5 0.95(3) . ? C14 C15 1.399(3) . ? C6 H6 0.94(3) . ? C15 C16 1.380(4) . ? C15 H15 0.98(3) . ? C19B C20B 1.507(5) . ? C19B H19C 0.9700 . ? C19B H19D 0.9700 . ? C16 H16 0.95(3) . ? C20B H20E 0.9600 . ? C20B H20F 0.9600 . ? C20B H20D 0.9600 . ? C20A C19A 1.509(9) . ? C20A H20A 0.9600 . ? C20A H20B 0.9600 . ? C20A H20C 0.9600 . ? C19A H19B 0.9700 . ? C19A H19A 0.9700 . ? 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 O3 V1 O4 102.03(7) . . ? O3 V1 O1 100.89(7) . . ? O4 V1 O1 105.17(6) . . ? O3 V1 O2 97.60(7) . . ? O4 V1 O2 91.29(6) . . ? O1 V1 O2 151.93(6) . . ? O3 V1 N1 96.82(7) . . ? O4 V1 N1 157.97(7) . . ? O1 V1 N1 82.09(6) . . ? O2 V1 N1 74.87(6) . . ? O3 V1 N3 175.58(7) . . ? O4 V1 N3 80.14(6) . . ? O1 V1 N3 82.12(6) . . ? O2 V1 N3 78.44(6) . . ? N1 V1 N3 80.33(6) . . ? C1 O1 V1 135.98(13) . . ? C12 O2 V1 117.71(13) . . ? C19B O4 V1 134.3(4) . . ? C19A O4 V1 119.7(5) . . ? C14 O5 H5O 108(2) . . ? C12 N2 N1 109.42(16) . . ? C11 N1 N2 115.58(17) . . ? C11 N1 V1 128.99(14) . . ? N2 N1 V1 115.42(12) . . ? C21 N3 C25 117.02(17) . . ? C21 N3 V1 120.20(13) . . ? C25 N3 V1 122.77(13) . . ? C21 C22 C23 118.95(18) . . ? C21 C22 H22 119.6(14) . . ? C23 C22 H22 121.3(14) . . ? O2 C12 N2 122.36(18) . . ? O2 C12 C13 119.10(19) . . ? N2 C12 C13 118.53(18) . . ? N3 C21 C22 123.67(19) . . ? N3 C21 H21 116.1(14) . . ? C22 C21 H21 120.1(14) . . ? N3 C25 C24 123.35(18) . . ? N3 C25 H25 117.3(14) . . ? C24 C25 H25 119.3(14) . . ? O1 C1 C10 122.33(18) . . ? O1 C1 C2 116.82(18) . . ? C10 C1 C2 120.76(19) . . ? C25 C24 C23 119.28(18) . . ? C25 C24 H24 118.2(12) . . ? C23 C24 H24 122.4(12) . . ? C1 C10 C11 120.03(19) . . ? C1 C10 C9 119.45(19) . . ? C11 C10 C9 120.33(19) . . ? C8 C9 C4 118.0(2) . . ? C8 C9 C10 123.4(2) . . ? C4 C9 C10 118.60(19) . . ? N1 C11 C10 123.70(19) . . ? N1 C11 H11 117.0(15) . . ? C10 C11 H11 119.2(15) . . ? C3 C2 C1 119.9(2) . . ? C3 C2 H2 122.4(15) . . ? C1 C2 H2 117.7(15) . . ? C24 C23 C22 117.72(17) . . ? C24 C23 C23 121.1(2) . 3_655 ? C22 C23 C23 121.2(2) . 3_655 ? C17 C18 C13 120.9(2) . . ? C17 C18 H18 120.7(15) . . ? C13 C18 H18 118.2(15) . . ? C5 C4 C3 121.6(2) . . ? C5 C4 C9 119.2(2) . . ? C3 C4 C9 119.24(19) . . ? C7 C8 C9 121.1(2) . . ? C7 C8 H8 117.1(14) . . ? C9 C8 H8 121.6(14) . . ? C2 C3 C4 122.0(2) . . ? C2 C3 H3 120.1(14) . . ? C4 C3 H3 117.9(14) . . ? C18 C13 C14 119.0(2) . . ? C18 C13 C12 119.5(2) . . ? C14 C13 C12 121.5(2) . . ? C18 C17 C16 119.6(2) . . ? C18 C17 H17 120.5(17) . . ? C16 C17 H17 119.8(17) . . ? C8 C7 C6 120.5(2) . . ? C8 C7 H7 118.7(15) . . ? C6 C7 H7 120.8(15) . . ? C6 C5 C4 121.3(2) . . ? C6 C5 H5 124.3(15) . . ? C4 C5 H5 114.4(15) . . ? O5 C14 C15 117.5(2) . . ? O5 C14 C13 123.10(19) . . ? C15 C14 C13 119.4(2) . . ? C5 C6 C7 119.8(2) . . ? C5 C6 H6 117.1(17) . . ? C7 C6 H6 123.1(17) . . ? C16 C15 C14 120.5(2) . . ? C16 C15 H15 121.9(18) . . ? C14 C15 H15 117.6(18) . . ? O4 C19B C20B 109.2(3) . . ? O4 C19B H19C 109.8 . . ? C20B C19B H19C 109.8 . . ? O4 C19B H19D 109.8 . . ? C20B C19B H19D 109.8 . . ? H19C C19B H19D 108.3 . . ? C15 C16 C17 120.5(2) . . ? C15 C16 H16 119.5(16) . . ? C17 C16 H16 120.0(16) . . ? C19B C20B H20E 109.5 . . ? C19B C20B H20F 109.5 . . ? H20E C20B H20F 109.5 . . ? C19B C20B H20D 109.5 . . ? H20E C20B H20D 109.5 . . ? H20F C20B H20D 109.5 . . ? C19A C20A H20A 109.5 . . ? C19A C20A H20B 109.5 . . ? H20A C20A H20B 109.5 . . ? C19A C20A H20C 109.5 . . ? H20A C20A H20C 109.5 . . ? H20B C20A H20C 109.5 . . ? O4 C19A C20A 108.4(9) . . ? O4 C19A H19B 110.0 . . ? C20A C19A H19B 110.0 . . ? O4 C19A H19A 110.0 . . ? C20A C19A H19A 110.0 . . ? H19B C19A H19A 108.4 . . ? 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 O3 V1 O1 C1 65.29(18) . . . . ? O4 V1 O1 C1 171.08(17) . . . . ? O2 V1 O1 C1 -65.0(2) . . . . ? N1 V1 O1 C1 -30.17(18) . . . . ? N3 V1 O1 C1 -111.43(18) . . . . ? O3 V1 O4 C19B -17.1(3) . . . . ? O1 V1 O4 C19B -122.0(3) . . . . ? O2 V1 O4 C19B 81.0(3) . . . . ? N1 V1 O4 C19B 131.2(4) . . . . ? N3 V1 O4 C19B 159.0(3) . . . . ? O3 V1 O4 C19A -33.0(13) . . . . ? O1 V1 O4 C19A -137.9(13) . . . . ? O2 V1 O4 C19A 65.1(13) . . . . ? N1 V1 O4 C19A 115.2(13) . . . . ? N3 V1 O4 C19A 143.1(13) . . . . ? C12 N2 N1 C11 177.73(16) . . . . ? C12 N2 N1 V1 -3.12(19) . . . . ? V1 O2 C12 N2 4.1(2) . . . . ? V1 O2 C12 C13 -175.05(13) . . . . ? N1 N2 C12 O2 -0.4(2) . . . . ? N1 N2 C12 C13 178.74(16) . . . . ? C25 N3 C21 C22 -0.3(3) . . . . ? V1 N3 C21 C22 179.06(15) . . . . ? C23 C22 C21 N3 0.5(3) . . . . ? C21 N3 C25 C24 0.1(3) . . . . ? V1 N3 C25 C24 -179.24(15) . . . . ? V1 O1 C1 C10 24.8(3) . . . . ? V1 O1 C1 C2 -158.59(14) . . . . ? N3 C25 C24 C23 -0.1(3) . . . . ? O1 C1 C10 C11 3.8(3) . . . . ? C2 C1 C10 C11 -172.67(18) . . . . ? O1 C1 C10 C9 178.75(16) . . . . ? C2 C1 C10 C9 2.3(3) . . . . ? C1 C10 C9 C8 179.02(18) . . . . ? C11 C10 C9 C8 -6.0(3) . . . . ? C1 C10 C9 C4 0.3(3) . . . . ? C11 C10 C9 C4 175.27(17) . . . . ? N2 N1 C11 C10 174.14(17) . . . . ? V1 N1 C11 C10 -4.9(3) . . . . ? C1 C10 C11 N1 -11.0(3) . . . . ? C9 C10 C11 N1 174.01(17) . . . . ? O1 C1 C2 C3 -179.74(18) . . . . ? C10 C1 C2 C3 -3.1(3) . . . . ? C25 C24 C23 C22 0.4(3) . . . . ? C25 C24 C23 C23 -179.57(14) . . . 3_655 ? C21 C22 C23 C24 -0.6(3) . . . . ? C21 C22 C23 C23 179.39(14) . . . 3_655 ? C8 C9 C4 C5 -0.8(3) . . . . ? C10 C9 C4 C5 177.98(17) . . . . ? C8 C9 C4 C3 179.08(18) . . . . ? C10 C9 C4 C3 -2.1(3) . . . . ? C4 C9 C8 C7 0.8(3) . . . . ? C10 C9 C8 C7 -177.94(19) . . . . ? C1 C2 C3 C4 1.2(3) . . . . ? C5 C4 C3 C2 -178.7(2) . . . . ? C9 C4 C3 C2 1.4(3) . . . . ? C17 C18 C13 C14 0.5(3) . . . . ? C17 C18 C13 C12 178.86(18) . . . . ? O2 C12 C13 C18 -1.1(3) . . . . ? N2 C12 C13 C18 179.72(18) . . . . ? O2 C12 C13 C14 177.24(18) . . . . ? N2 C12 C13 C14 -2.0(3) . . . . ? C13 C18 C17 C16 -0.4(3) . . . . ? C9 C8 C7 C6 0.0(3) . . . . ? C3 C4 C5 C6 -179.8(2) . . . . ? C9 C4 C5 C6 0.1(3) . . . . ? C18 C13 C14 O5 178.7(2) . . . . ? C12 C13 C14 O5 0.3(3) . . . . ? C18 C13 C14 C15 -0.2(3) . . . . ? C12 C13 C14 C15 -178.5(2) . . . . ? C4 C5 C6 C7 0.7(3) . . . . ? C8 C7 C6 C5 -0.8(3) . . . . ? O5 C14 C15 C16 -179.1(2) . . . . ? C13 C14 C15 C16 -0.2(4) . . . . ? C19A O4 C19B C20B -58(3) . . . . ? V1 O4 C19B C20B -104.6(4) . . . . ? C14 C15 C16 C17 0.3(4) . . . . ? C18 C17 C16 C15 0.0(3) . . . . ? C19B O4 C19A C20A 38.1(19) . . . . ? V1 O4 C19A C20A -178.4(10) . . . . ? _refine_diff_density_max 0.749 _refine_diff_density_min -0.289 _refine_diff_density_rms 0.052 _shelxl_version_number 2013-4 _shelx_res_file ; TITL CF solution in P4/n CELL 1.54184 21.5608 21.5608 10.1344 90.000 90.000 90.000 ZERR 4.00 0.0003 0.0003 0.0003 0.000 0.000 0.000 LATT 1 SYMM 1/2 - Y, X, Z SYMM 1/2 - X, 1/2 - Y, Z SYMM Y, 1/2 - X, Z SFAC C H N O V B UNIT 200 168 24 40 8 0 MERG 2 OMIT -2 4 8 OMIT 13 13 8 OMIT -3 4 1 OMIT -1 11 0 DFIX 1.54 C20B C19B DFIX 1.54 C20A C19A SADI 0.01 C20B C19B C19A C20A SADI 0.01 O4 C19B O4 C19A EADP C20B C20A EADP C19B C19A FMAP 2 PLAN 25 ACTA HTAB 2.00000 BOND $H CONF L.S. 4 WGHT 0.062900 1.361400 FVAR 2.54864 0.76994 0.77858 V1 5 0.507753 0.378683 0.321145 11.00000 0.02402 0.02943 = 0.02427 -0.00009 0.00057 0.00399 O3 4 0.442054 0.412785 0.333593 11.00000 0.03086 0.04132 = 0.03114 0.00132 -0.00037 0.00680 O1 4 0.544877 0.425460 0.189627 11.00000 0.02977 0.02919 = 0.02482 0.00004 0.00009 0.00330 O2 4 0.508143 0.339064 0.495911 11.00000 0.02702 0.03345 = 0.02552 0.00162 0.00289 0.00326 O4 4 0.487027 0.307537 0.243976 11.00000 0.03079 0.03290 = 0.03179 -0.00084 -0.00214 -0.00134 O5 4 0.612218 0.414579 0.809152 11.00000 0.07876 0.03462 = 0.02786 -0.00292 -0.00747 -0.00201 N2 3 0.567609 0.419309 0.572400 11.00000 0.03576 0.02857 = 0.02320 -0.00054 0.00088 0.00449 N1 3 0.557801 0.439917 0.443833 11.00000 0.02942 0.02905 = 0.02207 -0.00098 0.00118 0.00802 N3 3 0.605838 0.328328 0.320692 11.00000 0.02719 0.02585 = 0.02552 0.00003 0.00204 0.00202 C22 1 0.665240 0.235828 0.354703 11.00000 0.02908 0.02301 = 0.02823 0.00205 0.00118 0.00133 C12 1 0.539694 0.365803 0.589236 11.00000 0.02593 0.03148 = 0.02569 -0.00165 0.00386 0.00836 C21 1 0.610238 0.268516 0.354307 11.00000 0.02645 0.02750 = 0.02994 0.00048 0.00227 -0.00052 C25 1 0.658584 0.357295 0.286306 11.00000 0.03004 0.02312 = 0.02629 0.00125 0.00050 0.00270 C1 1 0.564213 0.483838 0.176881 11.00000 0.02193 0.03069 = 0.03109 0.00330 0.00068 0.00619 C24 1 0.715645 0.328457 0.284187 11.00000 0.02616 0.02660 = 0.02574 0.00073 0.00033 -0.00082 C10 1 0.581015 0.520184 0.285292 11.00000 0.02223 0.03138 = 0.02884 0.00036 0.00185 0.00833 C9 1 0.602873 0.583021 0.264094 11.00000 0.02174 0.03059 = 0.03553 0.00164 0.00274 0.00737 C11 1 0.581359 0.493696 0.415612 11.00000 0.02737 0.02799 = 0.02799 -0.00403 0.00127 0.00743 C2 1 0.570439 0.506868 0.046635 11.00000 0.02664 0.04069 = 0.02881 0.00266 -0.00081 0.00483 C23 1 0.719844 0.266306 0.319346 11.00000 0.02601 0.02664 = 0.02075 -0.00173 0.00010 0.00157 C18 1 0.515494 0.277606 0.738801 11.00000 0.02635 0.04067 = 0.03273 0.00249 0.00705 0.00734 C4 1 0.606236 0.605868 0.132572 11.00000 0.02332 0.03631 = 0.03974 0.00726 0.00124 0.00524 C8 1 0.619954 0.623365 0.367658 11.00000 0.02873 0.03285 = 0.03919 0.00108 0.00681 0.00568 C3 1 0.590223 0.566064 0.026435 11.00000 0.02939 0.04378 = 0.03187 0.01197 -0.00069 0.00491 C13 1 0.545199 0.334725 0.718466 11.00000 0.03416 0.03387 = 0.02545 0.00064 0.00531 0.01075 C17 1 0.520602 0.246785 0.857750 11.00000 0.03786 0.04119 = 0.03543 0.00760 0.01235 0.00816 C7 1 0.638582 0.683297 0.342568 11.00000 0.03260 0.03469 = 0.05029 -0.00206 0.00740 0.00178 C5 1 0.625584 0.667775 0.110744 11.00000 0.03276 0.03892 = 0.04557 0.01332 0.00336 0.00399 C14 1 0.580914 0.360245 0.820881 11.00000 0.05077 0.03248 = 0.02605 -0.00307 0.00483 0.00855 C6 1 0.641016 0.705687 0.212768 11.00000 0.03395 0.03212 = 0.06110 0.00491 0.00731 0.00040 C15 1 0.585931 0.328383 0.940700 11.00000 0.06601 0.04333 = 0.02377 -0.00418 -0.00029 0.01133 PART 1 C19B 1 0.430404 0.274948 0.226080 31.00000 0.03531 0.03766 = 0.04716 0.00019 -0.01174 -0.00633 AFIX 23 H19C 2 0.427386 0.260298 0.135811 31.00000 -1.20000 H19D 2 0.395665 0.302410 0.242970 31.00000 -1.20000 AFIX 0 PART 0 C16 1 0.555958 0.272441 0.958691 11.00000 0.05832 0.04524 = 0.02448 0.00496 0.00963 0.01438 PART 1 C20B 1 0.428280 0.220681 0.319763 21.00000 0.05527 0.04728 = 0.06369 0.01367 -0.00887 -0.01727 AFIX 137 H20E 2 0.460840 0.192054 0.298183 21.00000 -1.50000 H20F 2 0.388893 0.200223 0.312220 21.00000 -1.50000 H20D 2 0.433757 0.235207 0.408545 21.00000 -1.50000 AFIX 0 PART 2 C20A 1 0.423655 0.219516 0.196709 -21.00000 0.05527 0.04728 = 0.06369 0.01367 -0.00887 -0.01727 AFIX 137 H20A 2 0.424392 0.227828 0.103661 -21.00000 -1.50000 H20B 2 0.385629 0.198896 0.219155 -21.00000 -1.50000 H20C 2 0.458136 0.193473 0.219559 -21.00000 -1.50000 AFIX 0 C19A 1 0.428073 0.279815 0.271790 -31.00000 0.03531 0.03766 = 0.04716 0.00019 -0.01174 -0.00633 AFIX 23 H19B 2 0.394915 0.307489 0.244985 -31.00000 -1.20000 H19A 2 0.424126 0.272135 0.365724 -31.00000 -1.20000 AFIX 0 PART 0 H8 2 0.616535 0.611347 0.457400 11.00000 0.02772 H18 2 0.492381 0.258229 0.662005 11.00000 0.04131 H5 2 0.626474 0.679720 0.020871 11.00000 0.03628 H3 2 0.594875 0.581317 -0.059802 11.00000 0.03172 H11 2 0.601338 0.515643 0.485827 11.00000 0.03791 H25 2 0.655738 0.398826 0.262563 11.00000 0.03274 H2 2 0.560567 0.479242 -0.025071 11.00000 0.03665 H21 2 0.572249 0.247985 0.373226 11.00000 0.03101 H16 2 0.559773 0.251332 1.040943 11.00000 0.04657 H24 2 0.750971 0.351791 0.252413 11.00000 0.02485 H22 2 0.665529 0.194007 0.382194 11.00000 0.03053 H7 2 0.649301 0.710805 0.418895 11.00000 0.04599 H17 2 0.501506 0.208309 0.869945 11.00000 0.04550 H15 2 0.611536 0.346924 1.009565 11.00000 0.05963 H6 2 0.652885 0.746579 0.191537 11.00000 0.05352 H5O 2 0.606108 0.428941 0.727857 11.00000 0.08221 HKLF 4 REM CF solution in P4/n REM R1 = 0.0377 for 3576 Fo > 4sig(Fo) and 0.0452 for all 4129 data REM 381 parameters refined using 4 restraints END WGHT 0.0627 1.3748 REM Instructions for potential hydrogen bonds EQIV $1 -x+1, -y+1, -z+1 HTAB C11 O3_$1 HTAB C25 O1 EQIV $2 x, y, z-1 HTAB C2 O5_$2 HTAB O5 N2 REM Highest difference peak 0.749, deepest hole -0.289, 1-sigma level 0.052 Q1 1 0.2500 0.2500 0.3156 10.25000 0.05 0.75 Q2 1 0.2500 0.2500 0.1657 10.25000 0.05 0.55 Q3 1 0.5085 0.3729 0.4294 11.00000 0.05 0.51 Q4 1 0.5106 0.3813 0.2138 11.00000 0.05 0.45 Q5 1 0.5408 0.3490 0.6666 11.00000 0.05 0.28 Q6 1 0.2782 0.2228 0.1120 11.00000 0.05 0.27 Q7 1 0.5820 0.5040 0.3369 11.00000 0.05 0.26 Q8 1 0.5441 0.4209 0.3890 11.00000 0.05 0.25 Q9 1 0.6023 0.5944 0.2019 11.00000 0.05 0.24 Q10 1 0.5756 0.5068 0.2494 11.00000 0.05 0.24 Q11 1 0.5761 0.4374 0.6307 11.00000 0.05 0.23 Q12 1 0.5726 0.4997 0.1279 11.00000 0.05 0.22 Q13 1 0.5431 0.4249 0.2707 11.00000 0.05 0.22 Q14 1 0.5025 0.2663 0.8243 11.00000 0.05 0.21 Q15 1 0.6952 0.2505 0.3184 11.00000 0.05 0.20 Q16 1 0.6004 0.5841 0.0954 11.00000 0.05 0.19 Q17 1 0.6033 0.6005 0.3033 11.00000 0.05 0.19 Q18 1 0.5929 0.5611 0.2709 11.00000 0.05 0.18 Q19 1 0.4398 0.4163 0.4371 11.00000 0.05 0.18 Q20 1 0.5652 0.4312 0.5316 11.00000 0.05 0.18 Q21 1 0.6388 0.6871 0.2806 11.00000 0.05 0.18 Q22 1 0.4841 0.2290 0.6282 11.00000 0.05 0.17 Q23 1 0.5166 0.2520 0.7893 11.00000 0.05 0.17 Q24 1 0.5656 0.4314 0.4826 11.00000 0.05 0.16 Q25 1 0.5838 0.3421 0.8973 11.00000 0.05 0.16 ; _shelx_res_checksum 88077