# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics. # This journal is © the Owner Societies 2015 ####################################################################### # # 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_shelx _audit_block_doi 10.5517/cc1413mx _database_code_depnum_ccdc_archive 'CCDC 1043758' _audit_update_record ; 2015-01-15 deposited with the CCDC. 2015-03-23 downloaded from the CCDC. ; _audit_creation_method SHELXL-2014/7 _shelx_SHELXL_version_number 2014/7 _chemical_name_systematic 4-methoxy-1-naphtaldehyde _chemical_name_common ? _chemical_formula_moiety '(C12 H10 O2)0.6, (C12H10 O3)0.4' _chemical_formula_sum 'C12 H10 O2.40' _chemical_melting_point ? _exptl_crystal_description rectangle _exptl_crystal_colour Yellow _diffrn_ambient_temperature 200(2) _chemical_formula_weight 192.60 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' 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 14 _space_group_name_H-M_alt 'P 21/n' _space_group_name_Hall '-P 2yn' _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+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 15.074(2) _cell_length_b 3.9014(4) _cell_length_c 17.001(3) _cell_angle_alpha 90 _cell_angle_beta 110.532(11) _cell_angle_gamma 90 _cell_volume 936.3(2) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 3606 _cell_measurement_theta_min 1.55 _cell_measurement_theta_max 26.09 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.366 _exptl_crystal_F_000 405 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.070 _exptl_crystal_size_min 0.040 _exptl_absorpt_coefficient_mu 0.095 _shelx_estimated_absorpt_T_min 0.978 _shelx_estimated_absorpt_T_max 0.998 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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, 12 x 0.4 mm long-fine focus' _diffrn_measurement_device_type 'STOE IPDS 2' _diffrn_measurement_method 'rotation method' _diffrn_detector_area_resol_mean 6.67 _diffrn_reflns_number 11041 _diffrn_reflns_av_unetI/netI 0.0694 _diffrn_reflns_av_R_equivalents 0.1455 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.556 _diffrn_reflns_theta_max 24.990 _diffrn_reflns_theta_full 24.990 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_point_group_measured_fraction_full 1.000 _reflns_number_total 1660 _reflns_number_gt 823 _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_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^)+(0.0663P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment heteroxyz _refine_ls_extinction_method 'SHELXL-2014/7 (Sheldrick 2014' _refine_ls_extinction_coef 0.016(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1660 _refine_ls_number_parameters 140 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1244 _refine_ls_R_factor_gt 0.0590 _refine_ls_wR_factor_ref 0.1567 _refine_ls_wR_factor_gt 0.1317 _refine_ls_goodness_of_fit_ref 0.971 _refine_ls_restrained_S_all 0.971 _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 0.5595(2) 0.5012(8) 0.71074(18) 0.0575(8) Uani 1 1 d . . . . . C2 C 0.6471(2) 0.6449(8) 0.7527(2) 0.0604(9) Uani 1 1 d . . . . . H2 H 0.6821 0.7336 0.7204 0.072 Uiso 1 1 calc R U . . . C3 C 0.6865(2) 0.6665(8) 0.8391(2) 0.0638(9) Uani 1 1 d . . . . . H3 H 0.7473 0.7660 0.8651 0.077 Uiso 1 1 calc R U . . . C4 C 0.6374(2) 0.5438(8) 0.88669(18) 0.0573(8) Uani 1 1 d . . . . . C5 C 0.5464(2) 0.3912(8) 0.84839(18) 0.0557(8) Uani 1 1 d . . . . . C6 C 0.4956(2) 0.2611(8) 0.8976(2) 0.0639(9) Uani 1 1 d . . . . . H6 H 0.5226 0.2735 0.9571 0.077 Uiso 1 1 calc R U . . . C7 C 0.4085(3) 0.1183(9) 0.8609(2) 0.0733(10) Uani 1 1 d . . . . . H7 H 0.3750 0.0325 0.8947 0.088 Uiso 1 1 calc R U . . . C8 C 0.3689(2) 0.0977(9) 0.7748(2) 0.0719(10) Uani 1 1 d . . . . . H8 H 0.3080 -0.0024 0.7499 0.086 Uiso 1 1 calc R U . . . C9 C 0.4157(2) 0.2192(8) 0.7237(2) 0.0633(9) Uani 1 1 d . . . . . H9 H 0.3869 0.2020 0.6644 0.076 Uiso 1 1 calc R U . . . C10 C 0.5066(2) 0.3695(7) 0.75972(18) 0.0529(8) Uani 1 1 d . . . . . C11 C 0.5277(3) 0.4952(10) 0.6196(2) 0.0700(10) Uani 1 1 d . . . . . C12 C 0.7585(3) 0.7184(11) 1.0144(2) 0.0894(12) Uani 1 1 d . . . . . H12A H 0.8074 0.6079 0.9975 0.134 Uiso 1 1 calc R U . . . H12B H 0.7748 0.6953 1.0752 0.134 Uiso 1 1 calc R U . . . H12C H 0.7546 0.9619 0.9994 0.134 Uiso 1 1 calc R U . . . O1 O 0.45379(19) 0.3740(8) 0.57199(15) 0.0951(9) Uani 1 1 d . . . . . O2 O 0.66827(16) 0.5564(7) 0.97169(14) 0.0777(8) Uani 1 1 d . . . . . O3 O 0.5937(4) 0.6452(17) 0.5904(3) 0.0689(17) Uani 0.4 1 d . . P A 2 H3A H 0.572(4) 0.65(2) 0.537(6) 0.103 Uiso 0.4 1 calc R U P A 2 H11 H 0.5697 0.5918 0.5947 0.083 Uiso 0.6 1 d . U P B 1 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 0.0549(19) 0.056(2) 0.065(2) 0.0033(15) 0.0251(15) 0.0059(16) C2 0.0527(18) 0.057(2) 0.079(2) 0.0046(16) 0.0328(16) 0.0041(15) C3 0.0528(18) 0.059(2) 0.080(2) -0.0040(17) 0.0233(16) 0.0033(16) C4 0.0535(19) 0.056(2) 0.059(2) -0.0008(15) 0.0154(15) 0.0094(15) C5 0.0520(18) 0.0513(19) 0.069(2) 0.0032(15) 0.0279(15) 0.0089(14) C6 0.070(2) 0.056(2) 0.074(2) 0.0064(16) 0.0351(17) 0.0094(18) C7 0.072(2) 0.066(2) 0.101(3) 0.0093(19) 0.056(2) 0.0078(18) C8 0.056(2) 0.064(2) 0.105(3) -0.001(2) 0.0397(19) 0.0001(17) C9 0.0526(18) 0.057(2) 0.082(2) -0.0025(16) 0.0257(16) 0.0032(16) C10 0.0474(17) 0.0472(17) 0.067(2) 0.0003(14) 0.0243(14) 0.0072(14) C11 0.067(2) 0.076(3) 0.071(2) 0.0056(19) 0.0295(19) 0.0076(19) C12 0.071(2) 0.092(3) 0.085(3) -0.019(2) 0.0039(19) 0.006(2) O1 0.0765(17) 0.136(3) 0.0709(16) 0.0007(16) 0.0236(13) -0.0189(17) O2 0.0663(15) 0.0906(19) 0.0688(15) -0.0041(13) 0.0144(11) 0.0118(13) O3 0.051(3) 0.113(5) 0.044(3) 0.003(3) 0.019(2) -0.023(3) _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 C2 1.380(4) . ? C1 C10 1.435(4) . ? C1 C11 1.453(4) . ? C2 C3 1.381(4) . ? C2 H2 0.9500 . ? C3 C4 1.360(4) . ? C3 H3 0.9500 . ? C4 O2 1.355(3) . ? C4 C5 1.426(4) . ? C5 C6 1.412(4) . ? C5 C10 1.416(4) . ? C6 C7 1.359(5) . ? C6 H6 0.9500 . ? C7 C8 1.376(5) . ? C7 H7 0.9500 . ? C8 C9 1.380(5) . ? C8 H8 0.9500 . ? C9 C10 1.417(4) . ? C9 H9 0.9500 . ? C11 O1 1.220(4) . ? C11 O3 1.388(6) . ? C11 H11 0.955(4) . ? C12 O2 1.443(4) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? O3 H3A 0.85(10) . ? 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 C2 C1 C10 118.1(3) . . ? C2 C1 C11 117.1(3) . . ? C10 C1 C11 124.8(3) . . ? C1 C2 C3 123.4(3) . . ? C1 C2 H2 118.3 . . ? C3 C2 H2 118.3 . . ? C4 C3 C2 119.4(3) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? O2 C4 C3 124.5(3) . . ? O2 C4 C5 114.7(3) . . ? C3 C4 C5 120.8(3) . . ? C6 C5 C10 119.6(3) . . ? C6 C5 C4 121.0(3) . . ? C10 C5 C4 119.5(3) . . ? C7 C6 C5 120.8(3) . . ? C7 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? C6 C7 C8 120.1(3) . . ? C6 C7 H7 120.0 . . ? C8 C7 H7 120.0 . . ? C7 C8 C9 121.5(3) . . ? C7 C8 H8 119.3 . . ? C9 C8 H8 119.3 . . ? C8 C9 C10 120.0(3) . . ? C8 C9 H9 120.0 . . ? C10 C9 H9 120.0 . . ? C5 C10 C9 118.0(3) . . ? C5 C10 C1 118.8(3) . . ? C9 C10 C1 123.2(3) . . ? O1 C11 O3 122.0(4) . . ? O1 C11 C1 126.6(3) . . ? O3 C11 C1 111.4(3) . . ? O1 C11 H11 116.9(3) . . ? C1 C11 H11 116.4(3) . . ? O2 C12 H12A 109.5 . . ? O2 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O2 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C4 O2 C12 117.5(3) . . ? C11 O3 H3A 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 C10 C1 C2 C3 0.4(5) . . . . ? C11 C1 C2 C3 -179.6(3) . . . . ? C1 C2 C3 C4 -0.5(5) . . . . ? C2 C3 C4 O2 -178.8(3) . . . . ? C2 C3 C4 C5 0.5(5) . . . . ? O2 C4 C5 C6 -1.1(4) . . . . ? C3 C4 C5 C6 179.5(3) . . . . ? O2 C4 C5 C10 179.0(2) . . . . ? C3 C4 C5 C10 -0.4(4) . . . . ? C10 C5 C6 C7 -0.6(4) . . . . ? C4 C5 C6 C7 179.5(3) . . . . ? C5 C6 C7 C8 0.3(5) . . . . ? C6 C7 C8 C9 0.1(5) . . . . ? C7 C8 C9 C10 0.0(5) . . . . ? C6 C5 C10 C9 0.7(4) . . . . ? C4 C5 C10 C9 -179.4(3) . . . . ? C6 C5 C10 C1 -179.6(3) . . . . ? C4 C5 C10 C1 0.3(4) . . . . ? C8 C9 C10 C5 -0.4(4) . . . . ? C8 C9 C10 C1 180.0(3) . . . . ? C2 C1 C10 C5 -0.2(4) . . . . ? C11 C1 C10 C5 179.8(3) . . . . ? C2 C1 C10 C9 179.4(3) . . . . ? C11 C1 C10 C9 -0.6(5) . . . . ? C2 C1 C11 O1 178.5(4) . . . . ? C10 C1 C11 O1 -1.5(5) . . . . ? C2 C1 C11 O3 -0.8(5) . . . . ? C10 C1 C11 O3 179.2(4) . . . . ? C3 C4 O2 C12 1.5(4) . . . . ? C5 C4 O2 C12 -177.9(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H3A O1 0.85 1.76 2.599(5) 170.9 3_666 _refine_diff_density_max 0.168 _refine_diff_density_min -0.153 _refine_diff_density_rms 0.042 _shelx_res_file ; shelx.res created by SHELXL-2014/7 TITL ALD-OMe Y15 CELL 0.71073 15.0739 3.9014 17.0013 90.000 110.532 90.000 ZERR 4.00 0.0023 0.0004 0.0026 0.000 0.011 0.000 LATT 1 SYMM 1/2 - X, 1/2 + Y, 1/2 - Z SFAC C H O UNIT 48 40 9.6 MERG 2 OMIT 0.00 50.00 EQIV $1 -x+1, -y+1, -z+1 HTAB O3 O1_$1 FMAP 2 PLAN 10 SIZE 0.020 0.030 0.240 ACTA HTAB 2.00000 BOND $H CONF L.S. 12 TEMP -73.15 WGHT 0.066300 EXTI 0.015514 FVAR 0.84568 C1 1 0.559488 0.501234 0.710737 11.00000 0.05495 0.05557 = 0.06528 0.00329 0.02509 0.00591 C2 1 0.647062 0.644923 0.752659 11.00000 0.05268 0.05665 = 0.07947 0.00463 0.03277 0.00408 AFIX 43 H2 2 0.682053 0.733641 0.720369 11.00000 -1.20000 AFIX 0 C3 1 0.686490 0.666471 0.839124 11.00000 0.05283 0.05887 = 0.07976 -0.00396 0.02329 0.00332 AFIX 43 H3 2 0.747312 0.766031 0.865114 11.00000 -1.20000 AFIX 0 C4 1 0.637428 0.543836 0.886688 11.00000 0.05353 0.05586 = 0.05903 -0.00083 0.01544 0.00945 C5 1 0.546401 0.391180 0.848394 11.00000 0.05196 0.05129 = 0.06910 0.00319 0.02785 0.00894 C6 1 0.495599 0.261082 0.897610 11.00000 0.06968 0.05613 = 0.07378 0.00640 0.03512 0.00940 AFIX 43 H6 2 0.522597 0.273512 0.957110 11.00000 -1.20000 AFIX 0 C7 1 0.408530 0.118255 0.860897 11.00000 0.07236 0.06642 = 0.10140 0.00928 0.05563 0.00775 AFIX 43 H7 2 0.374997 0.032529 0.894743 11.00000 -1.20000 AFIX 0 C8 1 0.368901 0.097687 0.774774 11.00000 0.05615 0.06392 = 0.10481 -0.00105 0.03974 0.00008 AFIX 43 H8 2 0.307971 -0.002428 0.749903 11.00000 -1.20000 AFIX 0 C9 1 0.415655 0.219166 0.723734 11.00000 0.05257 0.05684 = 0.08217 -0.00251 0.02567 0.00321 AFIX 43 H9 2 0.386883 0.202047 0.664426 11.00000 -1.20000 AFIX 0 C10 1 0.506564 0.369455 0.759717 11.00000 0.04736 0.04724 = 0.06749 0.00034 0.02428 0.00724 C11 1 0.527722 0.495158 0.619597 11.00000 0.06680 0.07627 = 0.07133 0.00556 0.02955 0.00758 C12 1 0.758504 0.718377 1.014371 11.00000 0.07130 0.09243 = 0.08547 -0.01865 0.00392 0.00604 AFIX 137 H12A 2 0.807416 0.607894 0.997480 11.00000 -1.50000 H12B 2 0.774782 0.695298 1.075218 11.00000 -1.50000 H12C 2 0.754576 0.961894 0.999391 11.00000 -1.50000 AFIX 0 O1 3 0.453794 0.374034 0.571991 11.00000 0.07651 0.13603 = 0.07087 0.00068 0.02360 -0.01885 O2 3 0.668267 0.556419 0.971691 11.00000 0.06629 0.09061 = 0.06879 -0.00407 0.01439 0.01181 PART 2 O3 3 0.593745 0.645237 0.590421 10.40000 0.05131 0.11327 = 0.04430 0.00252 0.01947 -0.02252 AFIX 148 H3A 2 0.572497 0.646465 0.537344 10.40000 -1.50000 AFIX 0 PART 1 H11 2 10.569742 10.591811 10.594660 10.60000 -1.20000 HKLF 4 REM ALD-OMe Y15 REM R1 = 0.0590 for 823 Fo > 4sig(Fo) and 0.1244 for all 1660 data REM 140 parameters refined using 0 restraints END WGHT 0.0662 0.0000 REM Instructions for potential hydrogen bonds HTAB O3 O1_$1 REM Highest difference peak 0.168, deepest hole -0.153, 1-sigma level 0.042 Q1 1 0.6186 0.6656 0.6270 11.00000 0.05 0.17 Q2 1 0.5571 0.4636 0.5272 11.00000 0.05 0.16 Q3 1 0.6022 0.5361 0.8018 11.00000 0.05 0.15 Q4 1 0.4616 0.2354 0.6605 11.00000 0.05 0.15 Q5 1 0.5973 0.4472 0.6012 11.00000 0.05 0.13 Q6 1 0.4844 0.4423 0.6635 11.00000 0.05 0.12 Q7 1 0.4607 0.6469 0.5184 11.00000 0.05 0.12 Q8 1 0.3571 0.0366 0.6219 11.00000 0.05 0.12 Q9 1 0.5063 0.2164 1.0369 11.00000 0.05 0.11 Q10 1 0.3263 0.0662 0.6826 11.00000 0.05 0.11 ; _shelx_res_checksum 36300 _symmetry_cell_setting monoclinic _symmetry_space_group_name_h-m 'P 21/n' _symmetry_int_tables_number 14 _chemical_absolute_configuration . _chemical_properties_physical 'Air-sensitive, Oxygen-sensitive'