#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/34/2003466.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_2003466 loop_ _publ_author_name 'Ruiz-P\'erez, C.' 'Gonz\'alez-Platas, J.' 'Rodr\'iguez-Romero, F. V.' 'Gili, P.' 'Mart\'in-Zarza, P.' 'Mart\'in-Reyes, G.' 'Solans, X.' _publ_section_title 4,4'-Dimethoxy-2,2'-[dithiobis(o-phenylenenitrilomethylidyne)]diphenol _journal_issue 5 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1016 _journal_page_last 1018 _journal_paper_doi 10.1107/S0108270194008760 _journal_volume 51 _journal_year 1995 _chemical_formula_sum 'C28 H24 N2 O4 S2' _chemical_formula_weight 516.61 _chemical_name_systematic ; N-N'-[1,1'-ditiobis(phenylene)]bis(5'-metoxy-salicylideneimine) ; _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' _cell_angle_alpha 90.00 _cell_angle_beta 95.074(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 24.166(3) _cell_length_b 8.903(3) _cell_length_c 11.840(3) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 18 _cell_measurement_theta_min 6 _cell_volume 2537.4(11) _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989)' _computing_molecular_graphics 'PLUTO (Motherwell & Clegg, 1978)' _computing_structure_refinement 'SHELX76 (Sheldrick, 1976)' _computing_structure_solution 'SIR92 (Altomare et al., 1995)' _diffrn_ambient_temperature 293 _diffrn_measurement_device 'Enraf-Nonius CAD-4 diffractometer' _diffrn_measurement_method \w-2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_sigmaI/netI 0.0376 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 4576 _diffrn_reflns_reduction_process 'data average' _diffrn_reflns_theta_max 25.25 _diffrn_reflns_theta_min 1.69 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 60 _diffrn_standards_number 1 _exptl_absorpt_coefficient_mu 0.248 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.352 _exptl_crystal_description prism _exptl_crystal_F_000 1080 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _refine_diff_density_max .131 _refine_diff_density_min -.265 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_obs 0.879 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 211 _refine_ls_number_reflns 1913 _refine_ls_R_factor_obs 0.039 _refine_ls_shift/esd_max -0.368 _refine_ls_shift/esd_mean 0.0067 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(F)+0.004623F^2^]' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_obs 0.065 _reflns_number_observed 3755 _reflns_number_total 4152 _reflns_observed_criterion >2sigma(I) _cod_data_source_file ka1077.cif _cod_data_source_block sulfur _cod_depositor_comments ; The following automatic conversions were performed: '_refine_ls_weighting_scheme' value '1/[\s^2^(F)+0.004623F^2^]' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/[\s^2^(F)+0.004623F^2^]'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_cell_volume 2537.4(2) _cod_original_sg_symbol_H-M 'C 2/c' _cod_database_code 2003466 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_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_22 _atom_site_aniso_U_23 _atom_site_aniso_U_33 S1 0.0444(3) 0.0104(2) -0.0237(3) 0.0694(4) -0.0142(2) 0.0920(4) O1 0.0576(8) 0.0101(7) -0.0027(5) 0.0884(9) -0.0076(5) 0.0374(6) O2 0.0406(7) 0.0207(6) -0.0067(6) 0.0908(9) -0.0026(7) 0.0776(8) N1 0.0331(7) 0.0028(5) 0.0010(5) 0.0574(8) 0.0036(5) 0.0389(6) C1 0.0353(8) 0.0052(7) -0.0029(7) 0.0610(9) 0.0046(7) 0.0639(9) C2 0.0371(10) 0.0122(9) -0.0009(9) 0.0821(12) -0.0025(11) 0.0977(14) C3 0.0518(11) 0.0242(10) 0.0142(10) 0.0833(12) 0.0002(11) 0.0863(13) C4 0.0674(12) 0.0192(9) 0.0068(9) 0.0714(11) -0.0036(9) 0.0584(10) C5 0.0482(10) 0.0090(8) -0.0040(7) 0.0660(9) 0.0000(7) 0.0495(8) C6 0.0352(8) 0.0049(6) 0.0010(6) 0.0571(8) 0.0077(6) 0.0403(7) C7 0.0358(8) 0.0024(6) 0.0028(6) 0.0579(9) 0.0036(5) 0.0330(7) C8 0.0371(8) 0.0022(5) 0.0052(6) 0.0531(8) 0.0053(5) 0.0363(7) C9 0.0430(8) 0.0000(7) 0.0037(6) 0.0619(9) 0.0026(6) 0.0383(7) C10 0.0608(11) 0.0099(8) 0.0158(8) 0.0713(10) -0.0062(8) 0.0463(8) C11 0.0465(10) 0.0126(8) 0.0165(8) 0.0688(10) 0.0006(8) 0.0635(10) C12 0.0367(8) 0.0060(6) 0.0037(7) 0.0606(9) 0.0058(7) 0.0580(9) C13 0.0385(8) 0.0040(6) 0.0027(6) 0.0576(8) 0.0030(6) 0.0436(8) C14 0.0490(11) 0.0125(10) -0.0095(9) 0.0910(15) 0.0093(10) 0.0638(11) loop_ _atom_site_label _atom_site_occupancy _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_type_symbol S1 1 0.45929(2) 0.04313(5) 0.72175(5) 0.0704(2) Uani d S O1 1 0.30660(6) 0.10293(17) 0.76474(9) 0.0616(4) Uani d O O2 1 0.12317(5) 0.16347(17) 0.46009(12) 0.0704(5) Uani d O N1 1 0.35518(5) -0.04952(14) 0.60894(10) 0.0433(4) Uani d N C1 1 0.45311(7) -0.1016(2) 0.61794(15) 0.0538(5) Uani d C C2 1 0.49739(9) -0.1833(3) 0.5821(2) 0.0727(7) Uani d C C3 1 0.48888(9) -0.2943(2) 0.50218(19) 0.0733(8) Uani d C C4 1 0.43610(9) -0.3274(2) 0.45575(16) 0.0657(7) Uani d C C5 1 0.39166(8) -0.2459(2) 0.48992(13) 0.0551(5) Uani d C C6 1 0.39946(6) -0.13247(16) 0.56950(12) 0.0443(5) Uani d C C7 1 0.31176(6) -0.02478(17) 0.54247(11) 0.0422(5) Uani d C C8 1 0.26354(6) 0.05113(15) 0.57821(12) 0.0421(4) Uani d C C9 1 0.26244(7) 0.11268(19) 0.68706(12) 0.0477(5) Uani d C C10 1 0.21540(8) 0.1892(2) 0.71500(14) 0.0588(6) Uani d C C11 1 0.17011(7) 0.2025(2) 0.63819(15) 0.0589(6) Uani d C C12 1 0.17052(7) 0.14122(19) 0.53056(14) 0.0518(5) Uani d C C13 1 0.21694(7) 0.06702(18) 0.50053(13) 0.0466(5) Uani d C C14 1 0.12104(9) 0.0993(3) 0.35086(17) 0.0688(7) Uani d C H1O 1 0.3344(12) 0.0536(25) 0.7363(21) 0.081(7) Uiso d H H2 1 0.5317(12) -0.1600(28) 0.6063(20) 0.083(7) Uiso d H H3 1 0.5201(11) -0.3536(26) 0.4843(19) 0.078(6) Uiso d H H4 1 0.4290(10) -0.4111(26) 0.4029(18) 0.067(5) Uiso d H H5 1 0.3555(10) -0.2778(24) 0.4632(19) 0.070(6) Uiso d H H7 1 0.3094(8) -0.0581(18) 0.4642(16) 0.049(4) Uiso d H H10 1 0.2190(11) 0.2347(30) 0.7844(19) 0.082(6) Uiso d H H11 1 0.1380(11) 0.2645(25) 0.6559(16) 0.073(6) Uiso d H H13 1 0.2185(9) 0.0195(25) 0.4209(17) 0.068(6) Uiso d H H141 1 0.1254(10) -0.0105(31) 0.3508(17) 0.073(6) Uiso d H H142 1 0.0846(12) 0.1250(30) 0.3201(21) 0.086(7) Uiso d H H143 1 0.1522(11) 0.1396(26) 0.3077(20) 0.080(6) Uiso d H loop_ _atom_type_symbol _atom_type_description _atom_type_scat_source _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag C C International_Tables_Vol_IV_Table_2.3.1 0.002 0.002 H H International_Tables_Vol_IV_Table_2.3.1 0.000 0.000 N N International_Tables_Vol_IV_Table_2.3.1 0.004 0.003 O O International_Tables_Vol_IV_Table_2.3.1 0.008 0.006 S S International_Tables_Vol_IV_Table_2.3.1 0.110 0.124 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 12 2 -5 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag S1 S1 C1 2_656 2_656 104.40(7) yes C12 O2 C14 . . 117.4(2) yes C6 N1 C7 . . 119.50(10) yes S1 C1 C6 . . 116.40(10) yes S1 C1 C2 . . 124.70(10) yes C2 C1 C6 . . 118.8(2) yes C1 C2 C3 . . 121.0(2) yes C2 C3 C4 . . 120.5(2) yes C3 C4 C5 . . 119.1(2) yes C4 C5 C6 . . 121.3(2) yes C1 C6 C5 . . 119.3(2) yes N1 C6 C5 . . 123.00(10) yes N1 C6 C1 . . 117.60(10) yes N1 C7 C8 . . 122.80(10) yes C7 C8 C13 . . 118.60(10) yes C7 C8 C9 . . 122.30(10) yes C9 C8 C13 . . 119.10(10) yes O1 C9 C8 . . 121.5(2) yes C8 C9 C10 . . 119.50(10) yes O1 C9 C10 . . 118.90(10) yes C9 C10 C11 . . 120.6(2) yes C10 C11 C12 . . 120.5(2) yes O2 C12 C11 . . 115.4(2) yes C11 C12 C13 . . 119.9(2) yes O2 C12 C13 . . 124.6(2) yes C8 C13 C12 . . 120.50(10) yes 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 S1 S1 2_656 2.0210(10) yes S1 C1 . 1.778(2) yes O1 H1O . 0.89(3) ? O1 C9 . 1.349(2) yes O2 C12 . 1.370(2) yes O2 C14 . 1.411(3) yes N1 C6 . 1.413(2) yes N1 C7 . 1.274(2) yes C1 C2 . 1.391(3) yes C1 C6 . 1.398(2) yes C2 H2 . 0.88(3) ? C2 C3 . 1.372(3) yes C3 H3 . 0.96(3) ? C3 C4 . 1.375(3) yes C4 H4 . 0.98(2) ? C4 C5 . 1.386(3) yes C5 H5 . 0.95(2) ? C5 C6 . 1.383(2) yes C7 H7 . 0.970(18) ? C7 C8 . 1.442(2) yes C8 C9 . 1.403(2) yes C8 C13 . 1.397(2) yes C9 C10 . 1.390(3) yes C10 H10 . 0.91(2) ? C10 C11 . 1.365(2) yes C11 H11 . 0.99(3) ? C11 C12 . 1.387(2) yes C12 C13 . 1.375(2) yes C13 H13 . 1.04(2) ? C14 H141 . 0.98(3) ? C14 H142 . 0.95(3) ? C14 H143 . 1.01(3) ? 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_site_symmetry_1 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag S1 S1 C1 C2 2_656 . . -4.5(2) yes S1 S1 C1 C6 2_656 . . 176.00(10) yes C1 S1 S1 C1 . 2_656 2_656 -83.10(10) yes H1O O1 C9 C10 . . . -178.4(17) ? H1O O1 C9 C8 . . . -0.2(17) ? C12 O2 C14 H141 . . . 59.2(16) ? C12 O2 C14 H142 . . . 177.3(17) ? C12 O2 C14 H143 . . . -59.5(15) ? C14 O2 C12 C11 . . . -178.2(2) ? C14 O2 C12 C13 . . . 3.2(3) ? C6 N1 C7 H7 . . . -2.9(13) ? C6 N1 C7 C8 . . . 176.20(10) yes C7 N1 C6 C1 . . . 151.0(2) ? C7 N1 C6 C5 . . . -32.0(2) ? S1 C1 C6 N1 . . . -1.5(2) ? C2 C1 C6 N1 . . . 178.9(2) ? S1 C1 C6 C5 . . . -178.60(10) ? S1 C1 C2 H2 . . . -6.(2) ? S1 C1 C2 C3 . . . 179.3(2) ? C2 C1 C6 C5 . . . 1.8(3) ? C6 C1 C2 C3 . . . -1.2(3) ? C6 C1 C2 H2 . . . 174.(2) ? C1 C2 C3 H3 . . . -174.9(16) ? C1 C2 C3 C4 . . . -0.1(3) ? H2 C2 C3 H3 . . . 10.(3) ? H2 C2 C3 C4 . . . -175.4(19) ? C2 C3 C4 H4 . . . -175.4(15) ? C2 C3 C4 C5 . . . 0.7(3) ? H3 C3 C4 H4 . . . -1.(2) ? H3 C3 C4 C5 . . . 175.4(17) ? C3 C4 C5 H5 . . . -173.2(16) ? C3 C4 C5 C6 . . . 0.0(3) ? H4 C4 C5 H5 . . . 3.(2) ? H4 C4 C5 C6 . . . 176.2(15) ? C4 C5 C6 C1 . . . -1.3(3) ? C4 C5 C6 N1 . . . -178.2(2) ? H5 C5 C6 N1 . . . -5.2(16) ? H5 C5 C6 C1 . . . 171.7(16) ? N1 C7 C8 C9 . . . 4.6(2) ? N1 C7 C8 C13 . . . -177.10(10) ? H7 C7 C8 C9 . . . -176.3(12) ? H7 C7 C8 C13 . . . 2.0(12) ? C7 C8 C9 O1 . . . -0.5(2) ? C7 C8 C13 H13 . . . 2.3(14) ? C7 C8 C13 C12 . . . -178.70(10) ? C7 C8 C9 C10 . . . 177.7(2) ? C13 C8 C9 O1 . . . -178.80(10) ? C9 C8 C13 H13 . . . -179.3(14) ? C9 C8 C13 C12 . . . -0.4(2) ? C13 C8 C9 C10 . . . -0.6(2) ? C8 C9 C10 H10 . . . -173.7(18) ? O1 C9 C10 H10 . . . 4.5(18) ? C8 C9 C10 C11 . . . 1.1(3) ? O1 C9 C10 C11 . . . 179.4(2) ? C9 C10 C11 H11 . . . -174.6(15) ? C9 C10 C11 C12 . . . -0.7(3) ? H10 C10 C11 H11 . . . -0.(3) ? H10 C10 C11 C12 . . . 174.(2) ? C10 C11 C12 O2 . . . -179.0(2) ? H11 C11 C12 O2 . . . -5.0(15) ? C10 C11 C12 C13 . . . -0.3(3) ? H11 C11 C12 C13 . . . 173.7(15) ? O2 C12 C13 C8 . . . 179.4(2) ? C11 C12 C13 C8 . . . 0.8(3) ? C11 C12 C13 H13 . . . 179.7(14) ? O2 C12 C13 H13 . . . -1.7(14) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 136900174