#------------------------------------------------------------------------------ #$Date: 2025-08-19 12:52:15 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301804 $ #$URL: svn://www.crystallography.net/cod/cif/2/21/45/2214556.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_2214556 loop_ _publ_author_name 'Mohammed H. Al-Douh' 'Shafida A. Hamid' 'Hasnah Osman' 'Shea-Lin Ng' 'Hoong-Kun Fun' _publ_section_title ; 6,6'-Dimethoxy-2,2'-[m-phenylenebis(nitrilomethylidyne)]diphenol ; _journal_coeditor_code BT2439 _journal_issue 8 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o3570 _journal_page_last o3571 _journal_paper_doi 10.1107/S1600536807034812 _journal_volume 63 _journal_year 2007 _chemical_formula_iupac 'C22 H20 N2 O4' _chemical_formula_moiety 'C22 H20 N2 O4' _chemical_formula_sum 'C22 H20 N2 O4' _chemical_formula_weight 376.40 _chemical_name_common ; N,N'-Bis(2-hydroxy-3-methoxybenzylidene)1,3-diaminobenzene ; _chemical_name_systematic ; 6,6'-Dimethoxy-2,2'-[m-phenylenebis(nitrilomethylidyne)]diphenol ; _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 109.131(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 19.5677(7) _cell_length_b 6.8591(3) _cell_length_c 29.3903(11) _cell_measurement_reflns_used 5349 _cell_measurement_temperature 100.00(10) _cell_measurement_theta_max 30.30 _cell_measurement_theta_min 1.47 _cell_volume 3726.8(3) _computing_cell_refinement APEX2 _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_data_reduction 'SAINT (Bruker, 2005)' _computing_molecular_graphics SHELXTL _computing_publication_material ; SHELXTL and PLATON (Spek, 2003) ; _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 1998)' _diffrn_ambient_temperature 100.00(10) _diffrn_detector_area_resol_mean 8.33 _diffrn_measured_fraction_theta_full 0.985 _diffrn_measured_fraction_theta_max 0.985 _diffrn_measurement_device_type ; Bruker SMART APEX II CCD area-detector ; _diffrn_measurement_method \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 0.0305 _diffrn_reflns_av_sigmaI/netI 0.0355 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_limit_l_min -41 _diffrn_reflns_number 20168 _diffrn_reflns_theta_full 30.30 _diffrn_reflns_theta_max 30.30 _diffrn_reflns_theta_min 1.47 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_T_max 0.9785 _exptl_absorpt_correction_T_min 0.8925 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 2005)' _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.342 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1584 _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.41 _exptl_crystal_size_min 0.23 _refine_diff_density_max 0.254 _refine_diff_density_min -0.202 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 263 _refine_ls_number_reflns 5487 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.068 _refine_ls_R_factor_all 0.0779 _refine_ls_R_factor_gt 0.0483 _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^)+(0.0877P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1349 _refine_ls_wR_factor_ref 0.1587 _reflns_number_gt 3714 _reflns_number_total 5487 _reflns_threshold_expression I>2\s(I) _cod_data_source_file bt2439.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'C 2/c' _cod_database_code 2214556 _cod_database_fobs_code 2214556 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -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 O O1 0.48169(5) 0.71031(13) 0.12357(4) 0.0339(2) Uani d . 1 O O2 0.42622(5) 0.70622(12) 0.19363(4) 0.0337(3) Uani d . 1 O O3 0.41256(5) -0.02808(14) 0.47976(3) 0.0360(3) Uani d . 1 O O4 0.39662(5) 0.28910(15) 0.42757(4) 0.0345(2) Uani d . 1 N N1 0.37688(6) 0.89553(15) 0.25253(4) 0.0332(3) Uani d . 1 N N2 0.31250(6) 0.55350(17) 0.37499(4) 0.0342(3) Uani d . 1 C C1 0.44357(7) 0.88164(17) 0.17962(5) 0.0307(3) Uani d . 1 C C2 0.47494(7) 0.88652(18) 0.14290(5) 0.0325(3) Uani d . 1 C C3 0.49608(8) 1.0641(2) 0.12906(6) 0.0410(4) Uani d . 1 H H3A 0.5184 1.0676 0.1056 0.049 Uiso calc R 1 C C4 0.48410(10) 1.2363(2) 0.15010(6) 0.0483(4) Uani d . 1 H H4A 0.4987 1.3543 0.1407 0.058 Uiso calc R 1 C C5 0.45103(9) 1.2344(2) 0.18464(6) 0.0459(4) Uani d . 1 H H5A 0.4422 1.3512 0.1978 0.055 Uiso calc R 1 C C6 0.43032(7) 1.05683(19) 0.20024(5) 0.0349(3) Uani d . 1 C C7 0.39534(7) 1.05516(19) 0.23658(5) 0.0367(3) Uani d . 1 H H7A 0.3858 1.1732 0.2489 0.044 Uiso calc R 1 C C8 0.33731(7) 0.89671(18) 0.28512(5) 0.0334(3) Uani d . 1 C C9 0.28861(8) 1.0459(2) 0.28590(6) 0.0405(4) Uani d . 1 H H9A 0.2836 1.1543 0.2661 0.049 Uiso calc R 1 C C10 0.24824(8) 1.0302(2) 0.31643(6) 0.0445(4) Uani d . 1 H H10A 0.2163 1.1298 0.3171 0.053 Uiso calc R 1 C C11 0.25398(7) 0.8711(2) 0.34595(6) 0.0413(4) Uani d . 1 H H11A 0.2261 0.8632 0.3662 0.050 Uiso calc R 1 C C12 0.30233(7) 0.7206(2) 0.34523(5) 0.0343(3) Uani d . 1 C C13 0.34366(7) 0.73609(19) 0.31490(5) 0.0328(3) Uani d . 1 H H13A 0.3761 0.6373 0.3146 0.039 Uiso calc R 1 C C14 0.26012(7) 0.4806(2) 0.38664(5) 0.0371(3) Uani d . 1 H H14A 0.2148 0.5389 0.3751 0.045 Uiso calc R 1 C C15 0.26938(7) 0.3105(2) 0.41726(5) 0.0376(3) Uani d . 1 C C16 0.20960(8) 0.2280(3) 0.42651(6) 0.0516(5) Uani d . 1 H H16A 0.1644 0.2863 0.4140 0.062 Uiso calc R 1 C C17 0.21716(8) 0.0632(3) 0.45369(6) 0.0579(5) Uani d . 1 H H17A 0.1772 0.0106 0.4597 0.069 Uiso calc R 1 C C18 0.28455(8) -0.0272(3) 0.47251(6) 0.0491(4) Uani d . 1 H H18A 0.2893 -0.1394 0.4910 0.059 Uiso calc R 1 C C19 0.34440(7) 0.0503(2) 0.46362(5) 0.0361(3) Uani d . 1 C C20 0.33712(7) 0.2194(2) 0.43601(5) 0.0325(3) Uani d . 1 C C21 0.50031(8) 0.7139(2) 0.08047(6) 0.0399(4) Uani d . 1 H H21A 0.4984 0.5840 0.0680 0.060 Uiso calc R 1 H H21B 0.5483 0.7649 0.0874 0.060 Uiso calc R 1 H H21C 0.4667 0.7953 0.0570 0.060 Uiso calc R 1 C C22 0.42160(8) -0.2084(2) 0.50499(5) 0.0415(4) Uani d . 1 H H22A 0.4715 -0.2466 0.5147 0.062 Uiso calc R 1 H H22B 0.3924 -0.3066 0.4843 0.062 Uiso calc R 1 H H22C 0.4070 -0.1937 0.5329 0.062 Uiso calc R 1 H H2A 0.4091(9) 0.743(3) 0.2201(7) 0.054(5) Uiso d . 1 H H4B 0.3807(11) 0.392(3) 0.4071(8) 0.071(6) Uiso d . 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 O1 0.0321(5) 0.0275(5) 0.0410(6) 0.0002(4) 0.0107(4) 0.0058(4) O2 0.0350(5) 0.0188(5) 0.0480(7) -0.0009(4) 0.0145(5) 0.0020(4) O3 0.0245(5) 0.0483(6) 0.0332(5) -0.0027(4) 0.0065(4) 0.0031(4) O4 0.0207(4) 0.0419(6) 0.0408(6) 0.0003(4) 0.0099(4) -0.0004(5) N1 0.0276(5) 0.0248(6) 0.0384(7) 0.0034(4) -0.0013(5) -0.0030(5) N2 0.0254(5) 0.0406(7) 0.0330(6) 0.0049(5) 0.0047(5) -0.0097(5) C1 0.0245(6) 0.0198(6) 0.0385(8) -0.0009(4) -0.0020(5) 0.0055(5) C2 0.0246(6) 0.0247(7) 0.0393(8) -0.0014(5) -0.0015(6) 0.0072(5) C3 0.0387(8) 0.0327(8) 0.0403(9) -0.0068(6) -0.0022(6) 0.0144(6) C4 0.0577(10) 0.0262(7) 0.0462(10) -0.0104(6) -0.0034(8) 0.0127(7) C5 0.0525(9) 0.0177(7) 0.0488(10) -0.0014(6) -0.0088(8) 0.0030(6) C6 0.0316(7) 0.0219(6) 0.0385(8) 0.0016(5) -0.0058(6) 0.0023(5) C7 0.0327(7) 0.0223(6) 0.0408(8) 0.0053(5) -0.0075(6) -0.0056(6) C8 0.0249(6) 0.0296(7) 0.0359(8) 0.0039(5) -0.0032(6) -0.0103(6) C9 0.0320(7) 0.0321(7) 0.0443(9) 0.0105(6) -0.0052(6) -0.0082(6) C10 0.0334(7) 0.0411(8) 0.0483(9) 0.0173(6) -0.0013(7) -0.0141(7) C11 0.0274(7) 0.0472(9) 0.0417(8) 0.0109(6) 0.0010(6) -0.0152(7) C12 0.0238(6) 0.0372(8) 0.0338(8) 0.0057(5) -0.0016(5) -0.0113(6) C13 0.0230(6) 0.0291(7) 0.0392(8) 0.0067(5) 0.0003(6) -0.0095(6) C14 0.0215(6) 0.0564(9) 0.0301(7) 0.0070(6) 0.0038(6) -0.0090(6) C15 0.0223(6) 0.0623(10) 0.0269(7) 0.0011(6) 0.0063(5) -0.0054(6) C16 0.0208(7) 0.0974(14) 0.0370(9) 0.0051(7) 0.0101(6) 0.0044(9) C17 0.0258(7) 0.1075(15) 0.0429(10) -0.0062(8) 0.0147(7) 0.0139(10) C18 0.0299(7) 0.0806(12) 0.0361(9) -0.0060(7) 0.0099(7) 0.0115(8) C19 0.0226(6) 0.0594(9) 0.0247(7) -0.0022(6) 0.0058(5) -0.0027(6) C20 0.0207(6) 0.0510(9) 0.0255(7) -0.0023(5) 0.0072(5) -0.0072(6) C21 0.0355(7) 0.0430(8) 0.0390(8) 0.0019(6) 0.0092(6) 0.0109(7) C22 0.0342(7) 0.0578(10) 0.0287(7) -0.0065(7) 0.0053(6) 0.0059(7) 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 C2 O1 C21 116.28(10) C1 O2 H2A 101.6(10) C19 O3 C22 117.51(11) C20 O4 H4B 105.4(12) C7 N1 C8 121.48(11) C14 N2 C12 121.16(11) O2 C1 C2 118.15(11) O2 C1 C6 121.95(14) C2 C1 C6 119.90(12) O1 C2 C3 125.29(14) O1 C2 C1 115.21(10) C3 C2 C1 119.50(13) C4 C3 C2 120.36(16) C4 C3 H3A 119.8 C2 C3 H3A 119.8 C5 C4 C3 120.76(13) C5 C4 H4A 119.6 C3 C4 H4A 119.6 C4 C5 C6 120.37(14) C4 C5 H5A 119.8 C6 C5 H5A 119.8 C5 C6 C1 119.03(15) C5 C6 C7 120.29(13) C1 C6 C7 120.67(12) N1 C7 C6 122.19(12) N1 C7 H7A 118.9 C6 C7 H7A 118.9 C13 C8 C9 119.33(14) C13 C8 N1 117.82(11) C9 C8 N1 122.69(13) C10 C9 C8 119.34(14) C10 C9 H9A 120.3 C8 C9 H9A 120.3 C11 C10 C9 121.73(13) C11 C10 H10A 119.1 C9 C10 H10A 119.1 C10 C11 C12 119.31(15) C10 C11 H11A 120.3 C12 C11 H11A 120.3 C13 C12 C11 119.31(14) C13 C12 N2 117.69(11) C11 C12 N2 122.98(14) C8 C13 C12 120.98(12) C8 C13 H13A 119.5 C12 C13 H13A 119.5 N2 C14 C15 122.10(12) N2 C14 H14A 118.9 C15 C14 H14A 118.9 C16 C15 C20 118.94(15) C16 C15 C14 120.17(13) C20 C15 C14 120.81(12) C17 C16 C15 120.66(14) C17 C16 H16A 119.7 C15 C16 H16A 119.7 C16 C17 C18 120.46(14) C16 C17 H17A 119.8 C18 C17 H17A 119.8 C19 C18 C17 120.09(17) C19 C18 H18A 120.0 C17 C18 H18A 120.0 O3 C19 C18 124.81(15) O3 C19 C20 115.43(12) C18 C19 C20 119.76(13) O4 C20 C19 118.02(12) O4 C20 C15 121.89(13) C19 C20 C15 120.08(12) O1 C21 H21A 109.5 O1 C21 H21B 109.5 H21A C21 H21B 109.5 O1 C21 H21C 109.5 H21A C21 H21C 109.5 H21B C21 H21C 109.5 O3 C22 H22A 109.5 O3 C22 H22B 109.5 H22A C22 H22B 109.5 O3 C22 H22C 109.5 H22A C22 H22C 109.5 H22B C22 H22C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C2 1.3602(16) O1 C21 1.4285(18) O2 C1 1.3506(15) O2 H2A 0.975(18) O3 C19 1.3704(16) O3 C22 1.4229(18) O4 C20 1.3547(16) O4 H4B 0.91(2) N1 C7 1.2884(18) N1 C8 1.4156(19) N2 C14 1.2838(18) N2 C12 1.4156(19) C1 C2 1.406(2) C1 C6 1.4076(19) C2 C3 1.3895(18) C3 C4 1.388(2) C3 H3A 0.9300 C4 C5 1.371(3) C4 H4A 0.9300 C5 C6 1.407(2) C5 H5A 0.9300 C6 C7 1.445(2) C7 H7A 0.9300 C8 C13 1.387(2) C8 C9 1.4036(18) C9 C10 1.380(2) C9 H9A 0.9300 C10 C11 1.376(2) C10 H10A 0.9300 C11 C12 1.4051(18) C11 H11A 0.9300 C12 C13 1.390(2) C13 H13A 0.9300 C14 C15 1.448(2) C14 H14A 0.9300 C15 C16 1.404(2) C15 C20 1.4045(19) C16 C17 1.364(3) C16 H16A 0.9300 C17 C18 1.397(2) C17 H17A 0.9300 C18 C19 1.387(2) C18 H18A 0.9300 C19 C20 1.396(2) C21 H21A 0.9600 C21 H21B 0.9600 C21 H21C 0.9600 C22 H22A 0.9600 C22 H22B 0.9600 C22 H22C 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 _geom_hbond_publ_flag O2 H2A N1 1_555 0.98(2) 1.67(2) 2.590(2) 155(2) y O4 H4B N2 1_555 0.91(2) 1.75(2) 2.592(2) 151(2) y C4 H4A O1 1_565 0.93 2.50 3.340(2) 151 y C5 H5A O2 1_565 0.93 2.45 3.296(2) 151 y C22 H22A O4 5_656 0.96 2.60 3.502(2) 157 y C9 H9A Cg1 4_555 0.93 2.86 3.709(2) 152 y C11 H11A Cg2 1_565 0.93 2.9084 3.351(2) 111 y 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 C21 O1 C2 C3 -11.33(18) C21 O1 C2 C1 168.48(11) O2 C1 C2 O1 2.78(17) C6 C1 C2 O1 -176.44(11) O2 C1 C2 C3 -177.40(11) C6 C1 C2 C3 3.38(19) O1 C2 C3 C4 177.57(13) C1 C2 C3 C4 -2.2(2) C2 C3 C4 C5 -0.3(2) C3 C4 C5 C6 1.7(2) C4 C5 C6 C1 -0.5(2) C4 C5 C6 C7 -179.89(13) O2 C1 C6 C5 178.77(12) C2 C1 C6 C5 -2.04(19) O2 C1 C6 C7 -1.82(19) C2 C1 C6 C7 177.37(11) C8 N1 C7 C6 -174.64(11) C5 C6 C7 N1 -178.56(12) C1 C6 C7 N1 2.0(2) C7 N1 C8 C13 -154.90(12) C7 N1 C8 C9 29.79(19) C13 C8 C9 C10 0.27(19) N1 C8 C9 C10 175.51(13) C8 C9 C10 C11 -0.5(2) C9 C10 C11 C12 0.2(2) C10 C11 C12 C13 0.4(2) C10 C11 C12 N2 178.88(13) C14 N2 C12 C13 -148.15(13) C14 N2 C12 C11 33.3(2) C9 C8 C13 C12 0.31(19) N1 C8 C13 C12 -175.16(12) C11 C12 C13 C8 -0.6(2) N2 C12 C13 C8 -179.22(11) C12 N2 C14 C15 -179.64(12) N2 C14 C15 C16 -175.80(14) N2 C14 C15 C20 0.8(2) C20 C15 C16 C17 0.7(2) C14 C15 C16 C17 177.33(16) C15 C16 C17 C18 -0.5(3) C16 C17 C18 C19 -0.1(3) C22 O3 C19 C18 4.0(2) C22 O3 C19 C20 -175.40(12) C17 C18 C19 O3 -179.07(15) C17 C18 C19 C20 0.3(3) O3 C19 C20 O4 0.32(19) C18 C19 C20 O4 -179.14(14) O3 C19 C20 C15 179.36(13) C18 C19 C20 C15 -0.1(2) C16 C15 C20 O4 178.60(13) C14 C15 C20 O4 2.0(2) C16 C15 C20 C19 -0.4(2) C14 C15 C20 C19 -177.03(13) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 30655287 2 PubChem 136861718