#------------------------------------------------------------------------------ #$Date: 2025-08-19 12:52:15 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301804 $ #$URL: svn://www.crystallography.net/cod/cif/2/21/43/2214322.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_2214322 loop_ _publ_author_name 'Xiu-Ling Chen' 'Xu-Hong Yang' 'Ming-Hu Wu' _publ_section_title ; 1,1'-(N-Methyliminodimethylene)di-2-naphthol ; _journal_coeditor_code LH2426 _journal_issue 7 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o3246 _journal_page_last o3246 _journal_paper_doi 10.1107/S1600536807028826 _journal_volume 63 _journal_year 2007 _chemical_formula_iupac 'C23 H21 N O2' _chemical_formula_moiety 'C23 H21 N O2' _chemical_formula_sum 'C23 H21 N O2' _chemical_formula_weight 343.41 _chemical_name_systematic ; 1,1'-(N-Methyliminodimethylene)di-2-naphthol ; _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 _cell_angle_alpha 90.00 _cell_angle_beta 111.745(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 9.9947(10) _cell_length_b 24.319(3) _cell_length_c 8.0077(8) _cell_measurement_reflns_used 2957 _cell_measurement_temperature 297(2) _cell_measurement_theta_max 27.0 _cell_measurement_theta_min 1.67 _cell_volume 1807.9(3) _computing_cell_refinement 'SAINT (Bruker, 2001)' _computing_data_collection 'SMART (Bruker, 2001)' _computing_data_reduction SAINT _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material PLATON _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 297(2) _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method '\f and \w' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0736 _diffrn_reflns_av_sigmaI/netI 0.0571 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_number 10992 _diffrn_reflns_theta_full 27.00 _diffrn_reflns_theta_max 27.00 _diffrn_reflns_theta_min 1.67 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_T_max 0.9842 _exptl_absorpt_correction_T_min 0.9842 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 2001)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.262 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 728 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.223 _refine_diff_density_min -0.211 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 238 _refine_ls_number_reflns 3931 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.007 _refine_ls_R_factor_all 0.0800 _refine_ls_R_factor_gt 0.0552 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0754P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1343 _refine_ls_wR_factor_ref 0.1475 _reflns_number_gt 2738 _reflns_number_total 3931 _reflns_threshold_expression I>2\s(I) _cod_data_source_file lh2426.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2214322 _cod_database_fobs_code 2214322 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_type_symbol _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 C C1 0.73724(17) 0.18095(6) 0.1033(2) 0.0440(4) Uani d . 1 C C2 0.60649(18) 0.17833(6) -0.0501(2) 0.0465(4) Uani d . 1 C C3 0.5930(2) 0.19982(7) -0.2203(2) 0.0585(5) Uani d . 1 H H3 0.6719 0.2166 -0.2340 0.070 Uiso calc R 1 C C4 0.4662(2) 0.19623(9) -0.3641(3) 0.0782(6) Uani d . 1 H H4 0.4595 0.2108 -0.4743 0.094 Uiso calc R 1 C C5 0.3458(2) 0.17075(10) -0.3475(4) 0.0856(7) Uani d . 1 H H5 0.2600 0.1681 -0.4467 0.103 Uiso calc R 1 C C6 0.3547(2) 0.14998(9) -0.1864(4) 0.0781(6) Uani d . 1 H H6 0.2743 0.1334 -0.1762 0.094 Uiso calc R 1 C C7 0.4837(2) 0.15312(7) -0.0340(3) 0.0580(5) Uani d . 1 C C8 0.4956(2) 0.13167(8) 0.1361(3) 0.0692(6) Uani d . 1 H H8 0.4158 0.1154 0.1487 0.083 Uiso calc R 1 C C9 0.6205(3) 0.13447(7) 0.2796(3) 0.0642(5) Uani d . 1 H H9 0.6258 0.1203 0.3897 0.077 Uiso calc R 1 C C10 0.7420(2) 0.15858(6) 0.2630(2) 0.0499(4) Uani d . 1 C C11 0.86922(18) 0.20939(6) 0.0976(2) 0.0463(4) Uani d . 1 H H11A 0.8392 0.2429 0.0279 0.056 Uiso calc R 1 H H11B 0.9295 0.2199 0.2191 0.056 Uiso calc R 1 C C12 1.08916(19) 0.20732(8) 0.0432(2) 0.0589(5) Uani d . 1 H H12A 1.1515 0.2071 0.1676 0.088 Uiso calc R 1 H H12B 1.0650 0.2446 0.0038 0.088 Uiso calc R 1 H H12C 1.1374 0.1903 -0.0272 0.088 Uiso calc R 1 C C13 0.99320(18) 0.12140(6) 0.1021(2) 0.0458(4) Uani d . 1 H H13A 0.9073 0.1047 0.1089 0.055 Uiso calc R 1 H H13B 1.0636 0.1249 0.2236 0.055 Uiso calc R 1 C C14 1.05305(16) 0.08475(6) -0.0055(2) 0.0427(4) Uani d . 1 C C15 0.99667(18) 0.08809(7) -0.1903(2) 0.0488(4) Uani d . 1 C C16 1.0473(2) 0.05410(8) -0.2965(2) 0.0618(5) Uani d . 1 H H16 1.0078 0.0570 -0.4211 0.074 Uiso calc R 1 C C17 1.1534(2) 0.01729(8) -0.2174(3) 0.0666(5) Uani d . 1 H H17 1.1870 -0.0045 -0.2889 0.080 Uiso calc R 1 C C18 1.21416(19) 0.01128(7) -0.0292(3) 0.0560(5) Uani d . 1 C C19 1.3239(2) -0.02738(8) 0.0550(4) 0.0761(6) Uani d . 1 H H19 1.3605 -0.0485 -0.0151 0.091 Uiso calc R 1 C C20 1.3767(2) -0.03431(9) 0.2344(4) 0.0855(7) Uani d . 1 H H20 1.4486 -0.0602 0.2872 0.103 Uiso calc R 1 C C21 1.3235(2) -0.00268(8) 0.3408(3) 0.0724(6) Uani d . 1 H H21 1.3590 -0.0082 0.4645 0.087 Uiso calc R 1 C C22 1.22052(19) 0.03615(7) 0.2667(2) 0.0553(4) Uani d . 1 H H22 1.1883 0.0573 0.3411 0.066 Uiso calc R 1 C C23 1.16151(17) 0.04493(6) 0.0789(2) 0.0472(4) Uani d . 1 N N1 0.95721(13) 0.17670(5) 0.02054(16) 0.0413(3) Uani d . 1 O O1 0.87029(15) 0.16064(5) 0.40481(16) 0.0670(4) Uani d . 1 H H1 0.8592 0.1499 0.4959 0.101 Uiso calc R 1 O O2 0.88986(14) 0.12468(5) -0.27686(14) 0.0606(4) Uani d . 1 H H2 0.8808 0.1466 -0.2039 0.091 Uiso calc R 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 C1 0.0560(10) 0.0320(7) 0.0523(10) 0.0033(7) 0.0299(8) -0.0017(6) C2 0.0514(10) 0.0336(8) 0.0602(11) 0.0048(7) 0.0272(8) -0.0018(7) C3 0.0605(12) 0.0494(10) 0.0623(12) 0.0041(8) 0.0189(10) 0.0065(8) C4 0.0783(16) 0.0698(13) 0.0725(14) 0.0142(11) 0.0118(12) 0.0084(10) C5 0.0587(14) 0.0797(15) 0.0960(19) 0.0101(12) 0.0024(13) -0.0092(13) C6 0.0481(12) 0.0705(13) 0.1153(19) 0.0005(10) 0.0297(12) -0.0147(13) C7 0.0536(11) 0.0428(9) 0.0862(14) 0.0029(8) 0.0359(10) -0.0060(9) C8 0.0747(14) 0.0551(11) 0.1037(17) -0.0051(10) 0.0631(14) -0.0021(11) C9 0.0902(15) 0.0525(10) 0.0726(13) 0.0032(10) 0.0566(13) 0.0033(9) C10 0.0695(12) 0.0392(8) 0.0503(10) 0.0052(8) 0.0329(9) -0.0030(7) C11 0.0572(10) 0.0370(8) 0.0465(9) -0.0023(7) 0.0214(8) -0.0020(7) C12 0.0535(11) 0.0573(10) 0.0665(12) -0.0080(8) 0.0227(9) 0.0066(8) C13 0.0555(10) 0.0423(8) 0.0422(9) 0.0026(7) 0.0211(7) 0.0049(6) C14 0.0426(9) 0.0415(8) 0.0468(9) -0.0032(7) 0.0197(7) -0.0025(7) C15 0.0497(10) 0.0507(9) 0.0476(10) -0.0046(8) 0.0198(8) -0.0061(7) C16 0.0653(13) 0.0703(12) 0.0549(11) -0.0073(10) 0.0285(10) -0.0163(9) C17 0.0682(13) 0.0636(12) 0.0785(14) -0.0082(10) 0.0394(11) -0.0288(10) C18 0.0497(10) 0.0443(9) 0.0770(13) -0.0046(8) 0.0269(9) -0.0139(8) C19 0.0614(13) 0.0560(11) 0.1095(19) 0.0067(10) 0.0301(13) -0.0209(11) C20 0.0643(14) 0.0579(12) 0.119(2) 0.0163(11) 0.0164(14) -0.0014(13) C21 0.0629(13) 0.0599(12) 0.0839(14) 0.0095(10) 0.0151(11) 0.0084(10) C22 0.0519(10) 0.0468(9) 0.0643(12) 0.0017(8) 0.0183(9) 0.0019(8) C23 0.0437(9) 0.0384(8) 0.0605(11) -0.0068(7) 0.0205(8) -0.0051(7) N1 0.0455(8) 0.0386(7) 0.0418(7) -0.0007(5) 0.0185(6) 0.0047(5) O1 0.0897(10) 0.0674(8) 0.0474(7) -0.0020(7) 0.0294(7) 0.0016(6) O2 0.0686(8) 0.0718(8) 0.0389(6) 0.0099(7) 0.0171(6) -0.0005(5) 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 C10 C1 C2 119.27(15) C10 C1 C11 118.81(15) C2 C1 C11 121.88(14) C3 C2 C7 117.94(17) C3 C2 C1 122.84(15) C7 C2 C1 119.22(15) C4 C3 C2 121.07(19) C4 C3 H3 119.5 C2 C3 H3 119.5 C3 C4 C5 120.6(2) C3 C4 H4 119.7 C5 C4 H4 119.7 C6 C5 C4 119.8(2) C6 C5 H5 120.1 C4 C5 H5 120.1 C5 C6 C7 121.3(2) C5 C6 H6 119.4 C7 C6 H6 119.4 C6 C7 C2 119.21(18) C6 C7 C8 122.31(19) C2 C7 C8 118.48(18) C9 C8 C7 121.36(17) C9 C8 H8 119.3 C7 C8 H8 119.3 C8 C9 C10 120.17(17) C8 C9 H9 119.9 C10 C9 H9 119.9 O1 C10 C1 117.24(15) O1 C10 C9 121.27(16) C1 C10 C9 121.49(18) N1 C11 C1 115.40(12) N1 C11 H11A 108.4 C1 C11 H11A 108.4 N1 C11 H11B 108.4 C1 C11 H11B 108.4 H11A C11 H11B 107.5 N1 C12 H12A 109.5 N1 C12 H12B 109.5 H12A C12 H12B 109.5 N1 C12 H12C 109.5 H12A C12 H12C 109.5 H12B C12 H12C 109.5 N1 C13 C14 111.57(12) N1 C13 H13A 109.3 C14 C13 H13A 109.3 N1 C13 H13B 109.3 C14 C13 H13B 109.3 H13A C13 H13B 108.0 C15 C14 C23 119.13(14) C15 C14 C13 119.20(14) C23 C14 C13 121.60(14) O2 C15 C14 121.05(14) O2 C15 C16 117.68(15) C14 C15 C16 121.27(16) C17 C16 C15 120.03(18) C17 C16 H16 120.0 C15 C16 H16 120.0 C16 C17 C18 121.51(16) C16 C17 H17 119.2 C18 C17 H17 119.2 C17 C18 C19 122.06(17) C17 C18 C23 118.70(16) C19 C18 C23 119.24(18) C20 C19 C18 121.42(19) C20 C19 H19 119.3 C18 C19 H19 119.3 C19 C20 C21 119.81(19) C19 C20 H20 120.1 C21 C20 H20 120.1 C22 C21 C20 121.1(2) C22 C21 H21 119.5 C20 C21 H21 119.5 C21 C22 C23 121.22(17) C21 C22 H22 119.4 C23 C22 H22 119.4 C22 C23 C14 123.50(14) C22 C23 C18 117.19(16) C14 C23 C18 119.30(15) C12 N1 C11 108.78(12) C12 N1 C13 110.28(13) C11 N1 C13 112.90(11) C10 O1 H1 109.5 C15 O2 H2 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 C10 1.374(2) C1 C2 1.425(2) C1 C11 1.505(2) C2 C3 1.419(2) C2 C7 1.420(2) C3 C4 1.363(3) C3 H3 0.9300 C4 C5 1.403(3) C4 H4 0.9300 C5 C6 1.358(3) C5 H5 0.9300 C6 C7 1.411(3) C6 H6 0.9300 C7 C8 1.421(3) C8 C9 1.349(3) C8 H8 0.9300 C9 C10 1.398(3) C9 H9 0.9300 C10 O1 1.363(2) C11 N1 1.4793(19) C11 H11A 0.9700 C11 H11B 0.9700 C12 N1 1.466(2) C12 H12A 0.9600 C12 H12B 0.9600 C12 H12C 0.9600 C13 N1 1.4800(19) C13 C14 1.509(2) C13 H13A 0.9700 C13 H13B 0.9700 C14 C15 1.377(2) C14 C23 1.424(2) C15 O2 1.365(2) C15 C16 1.408(2) C16 C17 1.352(3) C16 H16 0.9300 C17 C18 1.408(3) C17 H17 0.9300 C18 C19 1.412(3) C18 C23 1.426(2) C19 C20 1.345(3) C19 H19 0.9300 C20 C21 1.391(3) C20 H20 0.9300 C21 C22 1.361(2) C21 H21 0.9300 C22 C23 1.414(2) C22 H22 0.9300 O1 H1 0.8200 O2 H2 0.8200 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 O1 H1 O2 1_556 0.82 1.84 2.633(2) 163.8 O2 H2 N1 . 0.82 1.83 2.557(2) 147.7 C6 H6 Cg2 1_455 0.93 2.82 3.698(3) 158 C19 H19 Cg1 3_755 0.93 2.78 3.564(2) 143 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 C10 C1 C2 C3 -179.24(14) ? C11 C1 C2 C3 3.0(2) ? C10 C1 C2 C7 0.6(2) ? C11 C1 C2 C7 -177.12(13) ? C7 C2 C3 C4 -0.2(2) ? C1 C2 C3 C4 179.62(16) ? C2 C3 C4 C5 -0.4(3) ? C3 C4 C5 C6 0.8(3) ? C4 C5 C6 C7 -0.4(3) ? C5 C6 C7 C2 -0.3(3) ? C5 C6 C7 C8 -179.99(18) ? C3 C2 C7 C6 0.6(2) ? C1 C2 C7 C6 -179.28(15) ? C3 C2 C7 C8 -179.70(14) ? C1 C2 C7 C8 0.5(2) ? C6 C7 C8 C9 179.13(18) ? C2 C7 C8 C9 -0.6(2) ? C7 C8 C9 C10 -0.3(3) ? C2 C1 C10 O1 178.20(13) ? C11 C1 C10 O1 -4.02(19) ? C2 C1 C10 C9 -1.5(2) ? C11 C1 C10 C9 176.24(14) ? C8 C9 C10 O1 -178.31(15) ? C8 C9 C10 C1 1.4(3) ? C10 C1 C11 N1 100.76(16) n C2 C1 C11 N1 -81.52(17) n N1 C13 C14 C15 -37.61(19) n N1 C13 C14 C23 145.50(14) n C23 C14 C15 O2 178.26(14) ? C13 C14 C15 O2 1.3(2) ? C23 C14 C15 C16 -2.0(2) ? C13 C14 C15 C16 -178.93(14) ? O2 C15 C16 C17 179.75(16) ? C14 C15 C16 C17 0.0(3) ? C15 C16 C17 C18 1.0(3) ? C16 C17 C18 C19 179.34(18) ? C16 C17 C18 C23 0.1(3) ? C17 C18 C19 C20 -177.14(19) ? C23 C18 C19 C20 2.1(3) ? C18 C19 C20 C21 -0.4(3) ? C19 C20 C21 C22 -1.3(3) ? C20 C21 C22 C23 1.4(3) ? C21 C22 C23 C14 179.63(16) ? C21 C22 C23 C18 0.2(2) ? C15 C14 C23 C22 -176.40(15) ? C13 C14 C23 C22 0.5(2) ? C15 C14 C23 C18 3.0(2) ? C13 C14 C23 C18 179.90(13) ? C17 C18 C23 C22 177.33(16) ? C19 C18 C23 C22 -1.9(2) ? C17 C18 C23 C14 -2.1(2) ? C19 C18 C23 C14 178.65(16) ? C1 C11 N1 C12 -173.60(13) ? C1 C11 N1 C13 -50.84(18) ? C14 C13 N1 C12 -70.89(16) ? C14 C13 N1 C11 167.19(12) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 210562 2 PubChem 240958