#------------------------------------------------------------------------------ #$Date: 2016-02-19 14:29:56 +0000 (Fri, 19 Feb 2016) $ #$Revision: 176759 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/55/2005514.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_2005514 loop_ _publ_author_name 'Ozturk, T.' 'Wallis, J. D.' _publ_section_title ; 6-(4-Methoxyphenyl)thieno[2,3-d][1,3]dithiole-2-thione at 150K ; _journal_issue 10 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 2552 _journal_page_last 2554 _journal_paper_doi 10.1107/S0108270196005264 _journal_volume 52 _journal_year 1996 _chemical_formula_sum 'C12 H8 O S4' _chemical_formula_weight 296.42 _chemical_name_systematic ; 6-(4-Methoxyphenyl)thieno[2,3-d]-1,3-dithiole-2-thione ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yab' _symmetry_space_group_name_H-M 'P 1 21/a 1' _audit_creation_method SHELXL _cell_angle_alpha 90.00 _cell_angle_beta 104.38(1) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.495(1) _cell_length_b 12.180(1) _cell_length_c 13.750(1) _cell_measurement_reflns_used 250 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 25.0 _cell_measurement_theta_min 2.3 _cell_volume 1215.9(2) _computing_cell_refinement SADONL _computing_data_collection 'SADONL (Pflugrath & Messerschmidt, 1989)' _computing_data_reduction SADONL _computing_molecular_graphics 'ZORTEP (Johnson, 1965)' _computing_publication_material SHELXL93 _computing_structure_refinement 'SHELXL93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1985)' _diffrn_measurement_device 'Enraf Nonius FAST system' _diffrn_measurement_method 'Method: see Danopoulos, Wilkinson, Hussain-Bates & Hursthouse (1991)' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'rotating anode source' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71069 _diffrn_reflns_av_R_equivalents 0.0754 _diffrn_reflns_av_sigmaI/netI 0.0742 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 4990 _diffrn_reflns_theta_max 25.03 _diffrn_reflns_theta_min 2.27 _exptl_absorpt_coefficient_mu 0.758 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_correction_T_min 0.80 _exptl_absorpt_correction_type 'refdelf (Walker & Stuart, 1983)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.619 _exptl_crystal_density_meas ? _exptl_crystal_description plate _exptl_crystal_F_000 608 _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.927 _refine_diff_density_min -0.616 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.011 _refine_ls_goodness_of_fit_obs 1.098 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 186 _refine_ls_number_reflns 1826 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.011 _refine_ls_restrained_S_obs 1.098 _refine_ls_R_factor_all 0.0632 _refine_ls_R_factor_obs 0.0551 _refine_ls_shift/esd_max 0.054 _refine_ls_shift/esd_mean 0.009 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0885P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1312 _refine_ls_wR_factor_obs 0.1288 _reflns_number_observed 1522 _reflns_number_total 1826 _reflns_observed_criterion >2sigma(I) _cod_data_source_file ha1162.cif _cod_data_source_block turan2 _cod_depositor_comments ; The following automatic conversions were performed: '_diffrn_ambient_temperature' value 'no' was changed to '?' - the value is undefined or not given. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+(0.0885P)^2^] where P=(Fo^2^+2Fc^2^)/3' 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^(Fo^2^)+(0.0885P)^2^] where P=(Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_sg_symbol_H-M 'P 21/a' _cod_database_code 2005514 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' 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 0.0217(5) 0.0323(6) 0.0186(5) 0.0005(3) 0.0041(4) 0.0037(4) S2 0.0330(6) 0.0534(7) 0.0279(6) 0.0097(4) 0.0051(4) 0.0144(5) S3 0.0238(5) 0.0519(7) 0.0173(5) 0.0023(4) 0.0023(4) -0.0020(4) S4 0.0299(6) 0.0365(6) 0.0257(6) -0.0051(4) 0.0035(4) -0.0087(4) O1 0.0312(13) 0.0303(15) 0.0168(14) -0.0015(10) 0.0011(10) 0.0004(11) C1 0.015(2) 0.051(3) 0.024(2) 0.001(2) 0.011(2) 0.000(2) C2 0.020(2) 0.038(2) 0.023(2) -0.0009(15) 0.0047(15) -0.005(2) C3 0.023(2) 0.030(2) 0.027(2) -0.002(2) 0.009(2) 0.000(2) C4 0.014(2) 0.029(2) 0.025(2) 0.0012(13) 0.0076(14) -0.004(2) C5 0.017(2) 0.033(2) 0.026(2) -0.0001(14) 0.0077(15) -0.002(2) C6 0.015(2) 0.024(2) 0.023(2) 0.0047(13) 0.0065(14) 0.0008(15) C7 0.023(2) 0.021(2) 0.022(2) 0.0010(14) 0.0028(14) 0.003(2) C8 0.026(2) 0.022(2) 0.019(2) 0.0043(14) 0.0077(15) 0.010(2) C9 0.014(2) 0.029(2) 0.020(2) 0.0061(13) 0.0012(13) -0.001(2) C10 0.015(2) 0.025(2) 0.023(2) 0.0000(14) 0.0048(14) 0.0040(15) C11 0.021(2) 0.025(2) 0.019(2) 0.0008(14) 0.0083(14) 0.004(2) C12 0.036(2) 0.051(3) 0.018(2) -0.003(2) 0.000(2) 0.006(2) 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 0.09374(12) 0.26719(8) 0.72981(7) 0.0244(3) Uani d S S2 1 -0.10318(13) 0.38504(9) 0.54524(7) 0.0386(3) Uani d S S3 1 -0.11270(11) 0.14127(9) 0.55835(7) 0.0315(3) Uani d S S4 1 -0.02150(12) -0.06915(8) 0.68906(7) 0.0313(3) Uani d S O1 1 0.5550(3) 0.2029(2) 1.2154(2) 0.0269(6) Uani d O C1 1 -0.0464(5) 0.2706(3) 0.6073(3) 0.0289(9) Uani d C C2 1 -0.0098(4) 0.0687(3) 0.6659(3) 0.0270(9) Uani d C C3 1 0.1075(5) -0.0493(3) 0.8093(3) 0.0264(9) Uani d C C4 1 0.1575(4) 0.0571(3) 0.8333(3) 0.0218(8) Uani d C C5 1 0.0882(4) 0.1252(3) 0.7472(3) 0.0247(9) Uani d C C6 1 0.2632(4) 0.0933(3) 0.9331(2) 0.0204(8) Uani d C C7 1 0.2560(4) 0.0340(3) 1.0193(3) 0.0224(8) Uani d C C8 1 0.3515(4) 0.0668(3) 1.1139(3) 0.0220(8) Uani d C C9 1 0.4588(4) 0.1619(3) 1.1258(2) 0.0217(8) Uani d C C10 1 0.4727(4) 0.2200(3) 1.0409(3) 0.0209(8) Uani d C C11 1 0.3752(4) 0.1862(3) 0.9467(3) 0.0210(8) Uani d C C12 1 0.5406(6) 0.1459(4) 1.3042(3) 0.0362(10) Uani d C H3 1 0.1323(46) -0.1024(32) 0.8490(29) 0.027(11) Uiso d H H7 1 0.1834(41) -0.0370(28) 1.0098(24) 0.016(8) Uiso d H H8 1 0.3448(40) 0.0257(27) 1.1615(26) 0.011(9) Uiso d H H10 1 0.5567(49) 0.2846(32) 1.0474(27) 0.031(10) Uiso d H H11 1 0.3873(43) 0.2298(27) 0.8949(27) 0.013(9) Uiso d H H121 1 0.6160(53) 0.1958(35) 1.3584(31) 0.041(11) Uiso d H H122 1 0.5730(49) 0.0657(36) 1.3069(29) 0.035(11) Uiso d H H123 1 0.4137(60) 0.1474(34) 1.3106(30) 0.050(13) Uiso d H 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 'Cromer and Mann (1968)' H H 0.0000 0.0000 'Stewart, Davidson and Simpson (1965)' O O 0.0106 0.0060 'Cromer and Mann (1968)' S S 0.1246 0.1234 'Cromer and Mann (1968)' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C5 S1 C1 97.3(2) C2 S3 C1 96.2(2) C3 S4 C2 89.9(2) C9 O1 C12 117.4(3) S2 C1 S3 124.0(2) S2 C1 S1 122.6(2) S3 C1 S1 113.4(2) C5 C2 S4 112.6(3) C5 C2 S3 118.6(3) S4 C2 S3 128.8(2) C4 C3 S4 114.9(3) C3 C4 C5 109.2(3) C3 C4 C6 124.1(3) C5 C4 C6 126.7(3) C2 C5 C4 113.4(3) C2 C5 S1 114.4(3) C4 C5 S1 132.1(3) C11 C6 C7 117.0(3) C11 C6 C4 122.4(3) C7 C6 C4 120.6(3) C8 C7 C6 121.9(3) C7 C8 C9 120.0(3) O1 C9 C10 116.1(3) O1 C9 C8 124.9(3) C10 C9 C8 119.0(3) C11 C10 C9 120.2(3) C10 C11 C6 121.9(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 C5 1.748(4) S1 C1 1.751(4) S2 C1 1.634(4) S3 C2 1.730(4) S3 C1 1.737(4) S4 C3 1.713(4) S4 C2 1.716(4) O1 C9 1.359(4) O1 C12 1.432(5) C2 C5 1.362(5) C3 C4 1.366(5) C4 C5 1.433(5) C4 C6 1.471(5) C6 C11 1.394(5) C6 C7 1.401(5) C7 C8 1.379(5) C8 C9 1.396(5) C9 C10 1.391(5) C10 C11 1.382(5)