#------------------------------------------------------------------------------ #$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $ #$Revision: 176760 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/33/2013327.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_2013327 loop_ _publ_author_name 'S. Kannan' 'Anwar Usman' 'Hoong-Kun Fun' _publ_section_title ; meso-Bis(phenylsulfinyl)methane ; _journal_issue 5 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o268 _journal_page_last o270 _journal_paper_doi 10.1107/S0108270103006991 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C13 H12 O2 S2' _chemical_formula_moiety 'C13 H12 O2 S2' _chemical_formula_sum 'C13 H12 O2 S2' _chemical_formula_weight 264.35 _chemical_name_systematic ; meso-Bis(phenylsulfinyl)methane ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 106.875(2) _cell_angle_beta 98.782(2) _cell_angle_gamma 90.897(2) _cell_formula_units_Z 2 _cell_length_a 8.2540(9) _cell_length_b 8.9037(10) _cell_length_c 9.0690(10) _cell_measurement_reflns_used 2403 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 28.30 _cell_measurement_theta_min 2.83 _cell_volume 629.05(12) _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_collection 'SMART (Siemens, 1996)' _computing_data_reduction SAINT _computing_molecular_graphics SHELXTL _computing_publication_material ; SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990) ; _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 8.33 _diffrn_measured_fraction_theta_full 0.943 _diffrn_measured_fraction_theta_max 0.943 _diffrn_measurement_device_type 'Siemens SMART 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 0.0136 _diffrn_reflns_av_sigmaI/netI 0.0272 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 3960 _diffrn_reflns_theta_full 28.30 _diffrn_reflns_theta_max 28.30 _diffrn_reflns_theta_min 2.83 _diffrn_standards_decay_% negligible _exptl_absorpt_coefficient_mu 0.409 _exptl_absorpt_correction_T_max 0.9450 _exptl_absorpt_correction_T_min 0.7915 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.396 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 276 _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.14 _refine_diff_density_max 0.258 _refine_diff_density_min -0.219 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.093 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 202 _refine_ls_number_reflns 2936 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.093 _refine_ls_R_factor_all 0.0469 _refine_ls_R_factor_gt 0.0378 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0386P)^2^+0.1734P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0892 _refine_ls_wR_factor_ref 0.0936 _reflns_number_gt 2466 _reflns_number_total 2936 _reflns_threshold_expression I>2\s(I) _cod_data_source_file na1603.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' 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 'Triclinic' changed to 'triclinic' 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_database_code 2013327 _cod_database_fobs_code 2013327 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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 S1 0.32060(5) 0.25191(5) 0.53573(5) 0.03953(13) Uani d . 1 . . S S2 0.21846(6) 0.06588(6) 0.19403(5) 0.04685(15) Uani d . 1 . . S O1 0.45788(16) 0.22187(18) 0.64959(16) 0.0542(4) Uani d . 1 . . O O2 0.09191(17) 0.1827(2) 0.18870(18) 0.0674(5) Uani d . 1 . . O C1 -0.0022(2) 0.3166(2) 0.5502(2) 0.0463(4) Uani d . 1 . . C C2 -0.1382(3) 0.3440(3) 0.6242(3) 0.0532(5) Uani d . 1 . . C C3 -0.1301(3) 0.3338(2) 0.7744(3) 0.0513(5) Uani d . 1 . . C C4 0.0134(3) 0.2966(2) 0.8517(2) 0.0490(5) Uani d . 1 . . C C5 0.1508(2) 0.2686(2) 0.7791(2) 0.0426(4) Uani d . 1 . . C C6 0.1411(2) 0.27821(19) 0.62845(19) 0.0366(4) Uani d . 1 . . C C7 0.2568(3) 0.0588(2) 0.3935(2) 0.0425(4) Uani d . 1 . . C C8 0.4110(2) 0.1612(2) 0.19247(19) 0.0377(4) Uani d . 1 . . C C9 0.5529(2) 0.0802(2) 0.1993(2) 0.0465(4) Uani d . 1 . . C C10 0.6983(3) 0.1509(3) 0.1879(2) 0.0553(5) Uani d . 1 . . C C11 0.7021(3) 0.2980(3) 0.1678(3) 0.0584(6) Uani d . 1 . . C C12 0.5603(3) 0.3767(3) 0.1595(3) 0.0590(6) Uani d . 1 . . C C13 0.4129(3) 0.3084(2) 0.1715(2) 0.0474(4) Uani d . 1 . . C H5 0.248(3) 0.246(2) 0.831(2) 0.048(5) Uiso d . 1 . . H H7B 0.343(3) -0.003(3) 0.406(3) 0.061(7) Uiso d . 1 . . H H2 -0.235(3) 0.367(3) 0.570(3) 0.071(7) Uiso d . 1 . . H H10 0.797(3) 0.098(3) 0.190(3) 0.068(7) Uiso d . 1 . . H H13 0.316(3) 0.355(3) 0.170(3) 0.060(6) Uiso d . 1 . . H H9 0.547(3) -0.022(3) 0.213(3) 0.058(6) Uiso d . 1 . . H H11 0.793(3) 0.341(3) 0.161(3) 0.071(7) Uiso d . 1 . . H H1 -0.006(3) 0.325(3) 0.448(3) 0.058(6) Uiso d . 1 . . H H3 -0.225(3) 0.352(3) 0.829(3) 0.067(7) Uiso d . 1 . . H H7A 0.161(3) 0.013(2) 0.413(2) 0.051(6) Uiso d . 1 . . H H4 0.020(3) 0.290(3) 0.952(3) 0.057(6) Uiso d . 1 . . H H12 0.560(3) 0.473(3) 0.139(3) 0.068(7) Uiso d . 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 S1 0.0367(2) 0.0426(2) 0.0412(2) 0.00252(17) 0.01047(18) 0.01328(18) S2 0.0339(2) 0.0648(3) 0.0394(2) -0.0039(2) 0.00764(18) 0.0112(2) O1 0.0354(7) 0.0688(9) 0.0548(8) 0.0069(6) 0.0015(6) 0.0154(7) O2 0.0326(7) 0.1150(14) 0.0685(10) 0.0178(8) 0.0108(7) 0.0468(10) C1 0.0454(10) 0.0532(11) 0.0438(10) 0.0115(8) 0.0086(8) 0.0186(9) C2 0.0421(11) 0.0571(12) 0.0625(13) 0.0143(9) 0.0103(9) 0.0194(10) C3 0.0484(12) 0.0485(11) 0.0586(12) 0.0074(9) 0.0227(10) 0.0111(9) C4 0.0574(12) 0.0512(11) 0.0411(10) 0.0050(9) 0.0176(9) 0.0127(9) C5 0.0431(10) 0.0469(10) 0.0398(9) 0.0063(8) 0.0070(8) 0.0158(8) C6 0.0375(9) 0.0358(8) 0.0370(9) 0.0034(7) 0.0088(7) 0.0103(7) C7 0.0449(11) 0.0419(9) 0.0427(10) 0.0030(8) 0.0142(8) 0.0118(8) C8 0.0314(8) 0.0487(10) 0.0317(8) 0.0024(7) 0.0077(6) 0.0086(7) C9 0.0394(10) 0.0524(11) 0.0489(11) 0.0090(8) 0.0120(8) 0.0141(9) C10 0.0353(10) 0.0758(15) 0.0519(12) 0.0069(10) 0.0126(8) 0.0116(10) C11 0.0439(12) 0.0788(16) 0.0496(12) -0.0139(11) 0.0131(9) 0.0124(11) C12 0.0686(15) 0.0549(13) 0.0537(12) -0.0101(11) 0.0091(10) 0.0177(10) C13 0.0447(11) 0.0516(11) 0.0457(10) 0.0079(9) 0.0078(8) 0.0137(9) 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' S S 0.1246 0.1234 '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 O1 S1 C6 107.30(10) yes O1 S1 C7 105.20(10) yes C6 S1 C7 98.00(10) yes O2 S2 C8 106.60(10) yes O2 S2 C7 106.10(10) yes C8 S2 C7 98.20(10) yes C2 C1 C6 119.05(18) ? C2 C1 H1 120.9(14) ? C6 C1 H1 120.0(14) ? C1 C2 C3 120.2(2) ? C1 C2 H2 118.6(16) ? C3 C2 H2 121.1(16) ? C4 C3 C2 120.33(19) ? C4 C3 H3 117.8(14) ? C2 C3 H3 121.9(14) ? C3 C4 C5 120.17(19) ? C3 C4 H4 120.8(14) ? C5 C4 H4 119.1(14) ? C6 C5 C4 119.04(18) ? C6 C5 H5 120.1(13) ? C4 C5 H5 120.8(13) ? C5 C6 C1 121.20(17) ? C5 C6 S1 119.76(14) ? C1 C6 S1 118.94(13) ? S2 C7 S1 112.99(10) ? S2 C7 H7B 109.8(14) ? S1 C7 H7B 104.9(15) ? S2 C7 H7A 107.9(13) ? S1 C7 H7A 112.0(12) ? H7B C7 H7A 109.1(19) ? C13 C8 C9 121.26(18) ? C13 C8 S2 119.17(14) ? C9 C8 S2 119.35(15) ? C10 C9 C8 118.8(2) ? C10 C9 H9 121.9(14) ? C8 C9 H9 119.2(14) ? C11 C10 C9 120.5(2) ? C11 C10 H10 118.1(15) ? C9 C10 H10 121.4(15) ? C10 C11 C12 120.2(2) ? C10 C11 H11 120.1(17) ? C12 C11 H11 119.7(17) ? C11 C12 C13 120.3(2) ? C11 C12 H12 121.0(15) ? C13 C12 H12 118.6(15) ? C8 C13 C12 118.9(2) ? C8 C13 H13 116.3(15) ? C12 C13 H13 124.8(15) ? 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 O1 . 1.495(2) yes S1 C6 . 1.798(2) yes S1 C7 . 1.837(2) yes S2 O2 . 1.491(2) yes S2 C8 . 1.794(2) yes S2 C7 . 1.808(2) yes C1 C2 . 1.383(3) ? C1 C6 . 1.385(3) ? C1 H1 . 0.94(2) ? C2 C3 . 1.383(3) ? C2 H2 . 0.93(2) ? C3 C4 . 1.378(3) ? C3 H3 . 0.98(2) ? C4 C5 . 1.386(3) ? C4 H4 . 0.92(2) ? C5 C6 . 1.384(2) ? C5 H5 . 0.92(2) ? C7 H7B . 0.92(2) ? C7 H7A . 0.95(2) ? C8 C13 . 1.378(3) ? C8 C9 . 1.388(2) ? C9 C10 . 1.378(3) ? C9 H9 . 0.95(2) ? C10 C11 . 1.375(3) ? C10 H10 . 0.95(2) ? C11 C12 . 1.377(3) ? C11 H11 . 0.85(3) ? C12 C13 . 1.385(3) ? C12 H12 . 0.93(2) ? C13 H13 . 0.91(2) ? 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 C1 H1 O2 1_555 0.95(3) 2.58(3) 3.363(2) 140(2) yes C5 H5 O1 1_555 0.92(2) 2.54(2) 2.939(2) 107(2) yes C13 H13 O2 1_555 0.91(2) 2.44(3) 2.904(3) 112(2) yes C4 H4 O2 1_556 0.92(3) 2.59(3) 3.465(2) 159(2) yes C7 H7B O1 2_656 0.92(3) 2.56(3) 3.441(3) 162(2) yes C9 H9 O1 2_656 0.95(3) 2.45(3) 3.360(2) 158(2) yes C10 H10 O2 1_655 0.95(3) 2.54(3) 3.255(3) 132(2) yes 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 C6 C1 C2 C3 0.3(3) ? C1 C2 C3 C4 0.1(3) ? C2 C3 C4 C5 -0.2(3) ? C3 C4 C5 C6 -0.2(3) ? C4 C5 C6 C1 0.6(3) ? C4 C5 C6 S1 176.94(15) ? C2 C1 C6 C5 -0.7(3) ? C2 C1 C6 S1 -177.06(16) ? O1 S1 C6 C5 0.05(17) ? C7 S1 C6 C5 108.79(15) ? O1 S1 C6 C1 176.45(15) ? C7 S1 C6 C1 -74.8(2) yes O2 S2 C7 S1 -56.60(10) yes C8 S2 C7 S1 53.41(12) ? O1 S1 C7 S2 -137.30(10) yes C6 S1 C7 S2 112.18(11) ? O2 S2 C8 C13 -6.38(17) ? C7 S2 C8 C13 -115.92(15) ? O2 S2 C8 C9 178.95(14) ? C7 S2 C8 C9 69.4(2) yes C13 C8 C9 C10 1.3(3) ? S2 C8 C9 C10 175.88(15) ? C8 C9 C10 C11 -1.0(3) ? C9 C10 C11 C12 0.3(3) ? C10 C11 C12 C13 0.1(3) ? C9 C8 C13 C12 -0.9(3) ? S2 C8 C13 C12 -175.52(15) ? C11 C12 C13 C8 0.2(3) ?