#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/27/2012761.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2012761 loop_ _publ_author_name 'Zhang, De-Chun' _publ_section_title ; The effect of molecular planarity on crystal non-centrosymmetry in benzylidene--aniline derivatives ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o351 _journal_page_last o352 _journal_paper_doi 10.1107/S0108270102006479 _journal_volume 58 _journal_year 2002 _chemical_formula_iupac 'C14 H12 N2 O3' _chemical_formula_moiety 'C14 H12 N2 O3' _chemical_formula_sum 'C14 H12 N2 O3' _chemical_formula_weight 256.26 _chemical_melting_point 430 _chemical_name_common N-(2-methoxyphenyl)-4-nitrophenylimine _chemical_name_systematic ; N-(2-methoxyphenyl)-4-nitrophenylimine ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 90 _cell_angle_beta 94.517(8) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.2703(6) _cell_length_b 7.2963(8) _cell_length_c 24.086(3) _cell_measurement_reflns_used 22 _cell_measurement_temperature 295(2) _cell_measurement_theta_max 12.77 _cell_measurement_theta_min 4.23 _cell_volume 1273.7(2) _computing_cell_refinement XSCANS _computing_data_collection 'XSCANS (Siemens, 1994)' _computing_data_reduction 'SHELXTL (Sheldrick, 1997a)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997b)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997b)' _diffrn_ambient_temperature 295(2) _diffrn_measured_fraction_theta_full 1.00 _diffrn_measured_fraction_theta_max 1.00 _diffrn_measurement_device_type 'Siemens P4' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0228 _diffrn_reflns_av_sigmaI/netI 0.0250 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_number 2876 _diffrn_reflns_theta_full 25.5 _diffrn_reflns_theta_max 25.50 _diffrn_reflns_theta_min 1.70 _diffrn_standards_decay_% 6 _diffrn_standards_interval_count 97 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type none _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.336 _exptl_crystal_density_meas 1.330 _exptl_crystal_density_method floatation _exptl_crystal_description 'square plate' _exptl_crystal_F_000 536 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.48 _exptl_crystal_size_min 0.46 _refine_diff_density_max 0.19 _refine_diff_density_min -0.24 _refine_ls_extinction_coef 0.036(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 174 _refine_ls_number_reflns 2372 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.001 _refine_ls_R_factor_all 0.059 _refine_ls_R_factor_gt 0.040 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0619P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.100 _refine_ls_wR_factor_ref 0.108 _reflns_number_gt 1662 _reflns_number_total 2372 _reflns_threshold_expression I>2\s(I) _cod_data_source_file gg1100.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_sg_symbol_Hall -p_2ybc _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2012761 _cod_database_fobs_code 2012761 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' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O1 0.14736(15) 0.40162(15) 0.21935(4) 0.0636(3) Uani d . 1 . . O O2 -0.22348(18) 1.44504(18) 0.01444(6) 0.0866(4) Uani d . 1 . . O O3 -0.41247(19) 1.22499(18) -0.00185(7) 0.0964(5) Uani d . 1 . . O N1 0.21159(17) 0.62637(16) 0.13563(5) 0.0497(3) Uani d . 1 . . N N2 -0.2667(2) 1.2858(2) 0.01814(6) 0.0613(4) Uani d . 1 . . N C1 0.3174(2) 0.38716(19) 0.19999(6) 0.0499(4) Uani d . 1 . . C C2 0.4523(3) 0.2662(2) 0.22012(7) 0.0650(5) Uani d . 1 . . C H2 0.4280 0.1839 0.2481 0.078 Uiso calc R 1 . . H C3 0.6231(3) 0.2668(3) 0.19894(8) 0.0749(6) Uani d . 1 . . C H3 0.7132 0.1851 0.2130 0.090 Uiso calc R 1 . . H C4 0.6620(3) 0.3858(3) 0.15748(8) 0.0719(5) Uani d . 1 . . C H4 0.7780 0.3861 0.1437 0.086 Uiso calc R 1 . . H C5 0.5258(2) 0.5059(2) 0.13624(6) 0.0605(4) Uani d . 1 . . C H5 0.5500 0.5846 0.1073 0.073 Uiso calc R 1 . . H C6 0.3551(2) 0.5101(2) 0.15747(6) 0.0470(4) Uani d . 1 . . C C7 0.2488(2) 0.7927(2) 0.12665(6) 0.0496(4) Uani d . 1 . . C H7 0.3667 0.8358 0.1373 0.059 Uiso calc R 1 . . H C8 0.1131(2) 0.91969(19) 0.10013(6) 0.0458(4) Uani d . 1 . . C C9 -0.0643(2) 0.8616(2) 0.08222(6) 0.0539(4) Uani d . 1 . . C H9 -0.0986 0.7409 0.0882 0.065 Uiso calc R 1 . . H C10 -0.1890(2) 0.9804(2) 0.05583(6) 0.0548(4) Uani d . 1 . . C H10 -0.3072 0.9413 0.0437 0.066 Uiso calc R 1 . . H C11 -0.1351(2) 1.1588(2) 0.04774(6) 0.0480(4) Uani d . 1 . . C C12 0.0377(2) 1.2217(2) 0.06513(6) 0.0543(4) Uani d . 1 . . C H12 0.0703 1.3431 0.0595 0.065 Uiso calc R 1 . . H C13 0.1619(2) 1.10074(19) 0.09119(6) 0.0524(4) Uani d . 1 . . C H13 0.2800 1.1409 0.1030 0.063 Uiso calc R 1 . . H C14 0.1085(3) 0.2874(3) 0.26450(9) 0.0992(7) Uani d . 1 . . C H14A 0.1140 0.1614 0.2533 0.119 Uiso calc R 1 . . H H14B -0.0127 0.3144 0.2754 0.119 Uiso calc R 1 . . H H14C 0.1978 0.3090 0.2953 0.119 Uiso calc R 1 . . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0629(7) 0.0636(7) 0.0642(7) -0.0021(6) 0.0043(6) 0.0155(6) O2 0.0877(10) 0.0574(8) 0.1132(11) 0.0082(7) -0.0010(8) 0.0269(7) O3 0.0717(9) 0.0817(10) 0.1293(12) 0.0042(7) -0.0341(9) 0.0131(8) N1 0.0573(8) 0.0447(7) 0.0463(7) 0.0038(6) -0.0011(6) 0.0023(6) N2 0.0623(9) 0.0585(9) 0.0625(8) 0.0096(8) 0.0022(7) 0.0069(7) C1 0.0592(10) 0.0435(8) 0.0454(8) 0.0003(7) -0.0061(7) -0.0027(7) C2 0.0816(12) 0.0539(10) 0.0572(10) 0.0103(9) -0.0093(9) 0.0064(8) C3 0.0807(13) 0.0697(12) 0.0713(12) 0.0297(10) -0.0122(10) -0.0023(10) C4 0.0651(11) 0.0824(13) 0.0683(11) 0.0209(10) 0.0062(9) -0.0108(10) C5 0.0694(11) 0.0626(10) 0.0498(9) 0.0096(9) 0.0072(8) -0.0012(8) C6 0.0551(9) 0.0437(8) 0.0406(7) 0.0050(7) -0.0057(6) -0.0042(6) C7 0.0546(9) 0.0497(9) 0.0435(8) 0.0008(7) -0.0020(7) -0.0016(7) C8 0.0542(9) 0.0435(8) 0.0392(7) 0.0002(7) 0.0000(7) -0.0024(6) C9 0.0599(10) 0.0417(8) 0.0593(9) -0.0044(7) 0.0002(8) 0.0044(7) C10 0.0499(9) 0.0543(9) 0.0592(10) -0.0034(7) -0.0027(7) 0.0015(8) C11 0.0563(9) 0.0460(8) 0.0414(7) 0.0065(7) 0.0025(7) 0.0009(7) C12 0.0647(10) 0.0393(8) 0.0581(9) -0.0030(8) 0.0003(8) 0.0017(7) C13 0.0547(9) 0.0461(9) 0.0547(9) -0.0043(7) -0.0063(7) -0.0023(7) C14 0.0918(15) 0.1074(17) 0.0997(15) -0.0120(13) 0.0151(12) 0.0452(13) 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C1 O1 C14 117.36(14) y C7 N1 C6 118.54(13) y O2 N2 O3 123.12(15) y O2 N2 C11 118.50(15) y O3 N2 C11 118.37(14) y O1 C1 C2 124.75(14) y O1 C1 C6 115.80(13) y C2 C1 C6 119.43(15) ? C1 C2 C3 120.27(16) ? C1 C2 H2 119.9 ? C3 C2 H2 119.9 ? C4 C3 C2 121.04(16) ? C4 C3 H3 119.5 ? C2 C3 H3 119.5 ? C3 C4 C5 119.08(17) ? C3 C4 H4 120.5 ? C5 C4 H4 120.5 ? C6 C5 C4 120.89(16) ? C6 C5 H5 119.6 ? C4 C5 H5 119.6 ? C5 C6 C1 119.27(14) ? C5 C6 N1 122.30(14) y C1 C6 N1 118.31(13) y N1 C7 C8 122.40(14) y N1 C7 H7 118.8 ? C8 C7 H7 118.8 ? C13 C8 C9 118.86(13) ? C13 C8 C7 119.87(13) ? C9 C8 C7 121.25(13) ? C10 C9 C8 120.85(14) ? C10 C9 H9 119.6 ? C8 C9 H9 119.6 ? C9 C10 C11 118.46(14) ? C9 C10 H10 120.8 ? C11 C10 H10 120.8 ? C12 C11 C10 122.46(14) ? C12 C11 N2 118.76(13) ? C10 C11 N2 118.76(14) ? C11 C12 C13 118.45(14) ? C11 C12 H12 120.8 ? C13 C12 H12 120.8 ? C12 C13 C8 120.90(14) ? C12 C13 H13 119.5 ? C8 C13 H13 119.5 ? O1 C14 H14A 109.5 ? O1 C14 H14B 109.5 ? H14A C14 H14B 109.5 ? O1 C14 H14C 109.5 ? H14A C14 H14C 109.5 ? H14B C14 H14C 109.5 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C1 . 1.3595(17) y O1 C14 . 1.416(2) y O2 N2 . 1.2087(17) y O3 N2 . 1.2131(17) y N1 C7 . 1.2661(18) y N1 C6 . 1.4136(18) y N2 C11 . 1.4748(19) y C1 C2 . 1.378(2) ? C1 C6 . 1.404(2) ? C2 C3 . 1.379(3) ? C2 H2 . 0.9300 ? C3 C4 . 1.369(3) ? C3 H3 . 0.9300 ? C4 C5 . 1.390(2) ? C4 H4 . 0.9300 ? C5 C6 . 1.379(2) ? C5 H5 . 0.9300 ? C7 C8 . 1.463(2) y C7 H7 . 0.9300 ? C8 C13 . 1.3890(19) ? C8 C9 . 1.393(2) ? C9 C10 . 1.374(2) ? C9 H9 . 0.9300 ? C10 C11 . 1.378(2) ? C10 H10 . 0.9300 ? C11 C12 . 1.372(2) ? C12 C13 . 1.378(2) ? C12 H12 . 0.9300 ? C13 H13 . 0.9300 ? C14 H14A . 0.9600 ? C14 H14B . 0.9600 ? C14 H14C . 0.9600 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA C10 H10 O3 3_475 0.93 2.51 3.4259(17) 167 C12 H12 O2 3_585 0.93 2.67 3.4376(19) 141 C9 H9 O2 1_545 0.93 2.90 3.5977(19) 133 C12 H12 N1 1_565 0.93 2.90 3.5861(17) 132 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_publ_flag C14 O1 C1 C2 1.9(2) y C14 O1 C1 C6 -176.30(15) ? O1 C1 C2 C3 -177.67(15) ? C6 C1 C2 C3 0.4(2) y C1 C2 C3 C4 -0.4(3) ? C2 C3 C4 C5 -0.7(3) ? C3 C4 C5 C6 1.9(3) ? C4 C5 C6 C1 -1.9(2) ? C4 C5 C6 N1 -177.91(14) ? O1 C1 C6 C5 179.00(13) ? C2 C1 C6 C5 0.7(2) ? O1 C1 C6 N1 -4.85(19) ? C2 C1 C6 N1 176.89(13) ? C7 N1 C6 C5 -46.8(2) ? C7 N1 C6 C1 137.14(15) y C6 N1 C7 C8 175.13(12) y N1 C7 C8 C13 -179.83(14) ? N1 C7 C8 C9 -1.5(2) y C13 C8 C9 C10 0.4(2) ? C7 C8 C9 C10 -177.99(14) ? C8 C9 C10 C11 -0.4(2) ? C9 C10 C11 C12 -0.2(2) ? C9 C10 C11 N2 178.43(13) ? O2 N2 C11 C12 -6.3(2) y O3 N2 C11 C12 172.93(15) ? O2 N2 C11 C10 175.07(15) ? O3 N2 C11 C10 -5.7(2) ? C10 C11 C12 C13 0.6(2) ? N2 C11 C12 C13 -177.98(13) ? C11 C12 C13 C8 -0.6(2) ? C9 C8 C13 C12 0.1(2) ? C7 C8 C13 C12 178.48(14) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 11196147