#------------------------------------------------------------------------------ #$Date: 2014-12-22 15:53:39 +0200 (Mon, 22 Dec 2014) $ #$Revision: 129005 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/11/60/7116084.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7116084 loop_ _publ_author_name 'Junya Yoshida' 'Akira Ueda' 'Akiko Nakao' 'Reiji Kumai' 'Hironori Nakao' 'Youichi Murakami' 'Hatsumi Mori' _publ_section_title ; Solid-solid phase interconversion in an organic conductor crystal: hydrogen-bond-mediated dynamic changes in pi-stacked molecular arrangement and physical properties ; _journal_name_full Chem.Commun. _journal_page_first 15557 _journal_paper_doi 10.1039/C4cc07810A _journal_volume 50 _journal_year 2014 _chemical_formula_moiety 'C12 H8 O4 S4' _chemical_formula_sum 'C12 H8 O4 S4' _chemical_formula_weight 344.43 _space_group_IT_number 20 _symmetry_cell_setting orthorhombic _symmetry_Int_Tables_number 20 _symmetry_space_group_name_Hall 'C 2c 2' _symmetry_space_group_name_H-M 'C 2 2 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.0000 _cell_angle_beta 90.0000 _cell_angle_gamma 90.0000 _cell_formula_units_Z 4 _cell_length_a 3.999(3) _cell_length_b 29.96(3) _cell_length_c 10.493(9) _cell_measurement_reflns_used 1699 _cell_measurement_temperature 293 _cell_measurement_theta_max 27.42 _cell_measurement_theta_min 3.34 _cell_volume 1257.2(19) _computing_cell_refinement CrystalClear _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction CrystalClear _computing_molecular_graphics 'CrystalStructure 4.0' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_structure_solution 'SIR2004 (Burla, et al., 2005)' _diffrn_ambient_temperature 293 _diffrn_detector_area_resol_mean 7.314 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'Rigaku Mercury70' _diffrn_measurement_method \w _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_reflns_av_R_equivalents 0.0632 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 38 _diffrn_reflns_limit_k_min -35 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 4826 _diffrn_reflns_theta_full 27.46 _diffrn_reflns_theta_max 27.46 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.764 _exptl_absorpt_correction_type none _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.820 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plete _exptl_crystal_F_000 704.00 _exptl_crystal_size_max 0.500 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.050 _refine_diff_density_max 0.500 _refine_diff_density_min -0.380 _refine_ls_abs_structure_details 'Flack, H. D. (1983), Acta Cryst. A39, 876-881. 567 Friedel Pairs' _refine_ls_abs_structure_Flack 0.8(3) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.142 _refine_ls_hydrogen_treatment mixed _refine_ls_number_parameters 96 _refine_ls_number_reflns 1440 _refine_ls_number_restraints 0 _refine_ls_R_factor_gt 0.0559 _refine_ls_shift/su_max 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0600P)^2^+0.7614P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.1364 _reflns_number_gt 1162 _reflns_number_total 1440 _reflns_threshold_expression F^2^>2.0\s(F^2^) _[local]_cod_data_source_file c4cc07810a2.cif _[local]_cod_data_source_block 20131027_Nutral _cod_original_cell_volume 1256.9(17) _cod_database_code 7116084 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 +X,-Y,-Z 3 -X,+Y,1/2-Z 4 -X,-Y,1/2+Z 5 1/2+X,1/2+Y,+Z 6 1/2+X,1/2-Y,-Z 7 1/2-X,1/2+Y,1/2-Z 8 1/2-X,1/2-Y,1/2+Z loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags S1 S 0.3223(3) 0.22814(3) 0.62534(11) 0.0322(3) Uani 1.0 8 d . S2 S 0.3174(3) 0.12071(3) 0.62528(11) 0.0333(3) Uani 1.0 8 d . O2 O 0.3213(9) 0.03212(10) 0.6290(3) 0.0459(8) Uani 1.0 8 d . O8 O 0.3547(11) 0.40107(10) 0.6361(4) 0.0478(10) Uani 1.0 8 d . C2 C 0.5000 0.19712(18) 0.7500 0.0279(13) Uani 1.0 4 d . C3 C 0.5000 0.15217(19) 0.7500 0.0299(14) Uani 1.0 4 d . C4 C 0.4203(11) 0.28061(13) 0.6909(4) 0.0289(10) Uani 1.0 8 d . C5 C 0.4256(12) 0.36031(13) 0.6904(4) 0.0320(11) Uani 1.0 8 d . C6 C 0.4193(12) 0.06927(13) 0.6954(4) 0.0353(12) Uani 1.0 8 d . C7 C 0.4938(16) -0.00674(14) 0.6782(5) 0.0545(15) Uani 1.0 8 d . C9 C 0.3437(10) 0.32066(13) 0.6316(4) 0.0292(8) Uani 1.0 8 d . H7A H 0.7199 -0.0073 0.6448 0.0654 Uiso 1.0 8 calc R H7B H 0.3804 -0.0335 0.6491 0.0654 Uiso 1.0 8 calc R H9 H 0.2379 0.3208 0.5527 0.0350 Uiso 1.0 8 calc R H10 H 0.244(14) 0.395(2) 0.587(5) 0.05(2) Uiso 1.0 8 d . 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 0.0412(6) 0.0223(5) 0.0331(6) -0.0003(5) -0.0035(7) -0.0012(5) S2 0.0403(6) 0.0239(5) 0.0357(6) -0.0013(5) -0.0029(8) 0.0004(5) O2 0.0535(19) 0.0262(15) 0.058(2) 0.0025(15) -0.012(3) -0.0063(15) O8 0.070(3) 0.0243(15) 0.049(3) 0.0046(17) -0.014(3) 0.0002(16) C2 0.036(4) 0.021(3) 0.027(3) 0.0000 0.007(3) 0.0000 C3 0.032(4) 0.028(3) 0.029(4) 0.0000 0.005(3) 0.0000 C4 0.027(3) 0.0191(18) 0.040(3) -0.0035(17) 0.003(2) -0.0028(17) C5 0.044(3) 0.0189(19) 0.033(3) 0.0034(18) 0.002(3) 0.0020(17) C6 0.048(3) 0.020(2) 0.038(3) -0.001(2) -0.000(2) -0.0019(17) C7 0.067(4) 0.019(3) 0.078(4) 0.004(3) -0.013(4) -0.001(3) C9 0.035(2) 0.033(2) 0.0188(18) 0.0002(19) -0.005(3) -0.0039(19) 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 for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.0106 0.0060 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; S S 0.1246 0.1234 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 C2 S1 C4 95.2(2) yes . . C3 S2 C6 93.5(3) yes . . C6 O2 C7 109.6(4) yes . . S1 C2 S1 116.1(3) yes . 3_656 S1 C2 C3 121.97(16) yes . . S1 C2 C3 121.97(16) yes 3_656 . S2 C3 S2 115.7(4) yes . 3_656 S2 C3 C2 122.16(17) yes . . S2 C3 C2 122.16(17) yes 3_656 . S1 C4 C4 116.7(3) yes . 3_656 S1 C4 C9 123.2(3) yes . . C4 C4 C9 120.0(4) yes 3_656 . O8 C5 C5 117.5(4) yes . 3_656 O8 C5 C9 122.0(4) yes . . C5 C5 C9 120.4(4) yes 3_656 . S2 C6 O2 115.7(3) yes . . S2 C6 C6 118.6(4) yes . 3_656 O2 C6 C6 125.7(4) yes . 3_656 O2 C7 C7 111.8(4) yes . 3_656 C4 C9 C5 119.5(4) yes . . C5 O8 H10 102(5) no . . O2 C7 H7A 109.252 no . . O2 C7 H7B 109.249 no . . C7 C7 H7A 109.250 no 3_656 . C7 C7 H7B 109.256 no 3_656 . H7A C7 H7B 107.929 no . . C4 C9 H9 120.248 no . . C5 C9 H9 120.257 no . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_2 S1 C2 1.755(4) yes . S1 C4 1.760(5) yes . S2 C3 1.770(4) yes . S2 C6 1.756(5) yes . O2 C6 1.370(6) yes . O2 C7 1.448(6) yes . O8 C5 1.377(6) yes . C2 C3 1.347(8) yes . C4 C4 1.394(6) yes 3_656 C4 C9 1.386(6) yes . C5 C5 1.385(6) yes 3_656 C5 C9 1.378(6) yes . C6 C6 1.315(7) yes 3_656 C7 C7 1.508(7) yes 3_656 O8 H10 0.70(6) no . C7 H7A 0.970 no . C7 H7B 0.970 no . C9 H9 0.930 no . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_2 S1 S2 3.218(3) no . O2 O2 2.913(5) no 3_656 O8 O8 2.657(6) no 3_656 C2 C4 2.596(7) no 3_656 C3 C6 2.569(7) no 3_656 C4 C5 2.762(6) no 3_656 C6 C7 2.658(7) no 3_656 C9 C9 2.782(6) no 3_656 S1 S1 3.554(3) no 6_456 S1 S1 3.554(3) no 6_556 S2 O8 3.372(5) no 6_456 S2 O8 3.545(5) no 6_556 O2 O2 3.322(5) no 2_556 O2 C7 3.546(8) no 1_455 O2 C7 3.383(7) no 2_556 O8 S2 3.545(5) no 6_456 O8 S2 3.372(5) no 6_556 O8 C7 3.147(6) no 5_455 C4 C4 3.582(7) no 3_556 C6 C6 3.544(7) no 3_556 C7 O2 3.546(8) no 1_655 C7 O2 3.383(7) no 2_556 C7 O8 3.147(6) no 5_545 S1 H9 2.8975 no . O2 H7A 2.6555 no 3_656 O2 H7B 3.2717 no 3_656 O8 H9 2.6023 no . O8 H10 3.32(6) no 3_656 C4 H9 3.2487 no 3_656 C5 H9 3.2377 no 3_656 C5 H10 2.88(6) no 3_656 C6 H7A 2.6437 no . C6 H7A 2.8954 no 3_656 C6 H7B 3.1202 no . C6 H7B 3.5749 no 3_656 C9 H10 2.31(6) no . H7A H7A 2.8221 no 3_656 H7A H7B 2.3345 no 3_656 H7B H7B 2.3231 no 3_656 H9 H10 2.2534 no . S1 H9 3.3313 no 6_456 S1 H9 2.8976 no 6_556 S2 H9 3.4539 no 6_456 S2 H9 3.0638 no 6_556 S2 H10 3.23(6) no 6_456 S2 H10 2.85(6) no 6_556 O2 H7A 2.6844 no 1_455 O2 H7A 3.3692 no 2_556 O2 H7B 2.9285 no 2_556 O2 H10 3.57(6) no 6_556 O8 H7A 2.7985 no 5_455 O8 H7B 2.7311 no 5_455 O8 H7B 2.8777 no 5_555 O8 H7B 3.1311 no 7_556 O8 H10 3.60(6) no 1_655 C2 H9 3.3581 no 6_556 C2 H9 3.3581 no 8_555 C3 H9 3.4127 no 6_556 C3 H9 3.4127 no 8_555 C6 H10 3.41(6) no 6_556 C7 H7A 3.1142 no 1_455 C7 H7A 3.5332 no 2_556 C7 H10 3.25(6) no 5_545 H7A O2 2.6844 no 1_655 H7A O2 3.3692 no 2_556 H7A O8 2.7985 no 5_545 H7A C7 3.1142 no 1_655 H7A C7 3.5332 no 2_556 H7A H7A 3.0709 no 2_556 H7A H7A 3.1443 no 3_756 H7A H7B 2.7554 no 1_655 H7A H7B 3.5848 no 2_556 H7A H10 2.9896 no 5_545 H7B O2 2.9285 no 2_556 H7B O8 2.8777 no 5_445 H7B O8 2.7311 no 5_545 H7B O8 3.1311 no 7_546 H7B H7A 2.7554 no 1_455 H7B H7A 3.5848 no 2_556 H7B H10 3.3897 no 5_445 H7B H10 2.6688 no 5_545 H7B H10 3.5342 no 7_546 H9 S1 2.8976 no 6_456 H9 S1 3.3313 no 6_556 H9 S2 3.0638 no 6_456 H9 S2 3.4539 no 6_556 H9 C2 3.3581 no 6_456 H9 C3 3.4127 no 6_456 H10 S2 2.85(6) no 6_456 H10 S2 3.23(6) no 6_556 H10 O2 3.57(6) no 6_456 H10 O8 3.60(6) no 1_455 H10 C6 3.41(6) no 6_456 H10 C7 3.25(6) no 5_455 H10 H7A 2.9896 no 5_455 H10 H7B 2.6688 no 5_455 H10 H7B 3.3897 no 5_555 H10 H7B 3.5342 no 7_556 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C2 S1 C4 C4 -1.7(3) no . . 3_656 C2 S1 C4 C9 178.9(3) no . . . C4 S1 C2 S1 0.51(15) no . . 3_656 C4 S1 C2 C3 -179.49(14) no . . . C3 S2 C6 O2 179.9(3) no . . . C3 S2 C6 C6 -0.3(4) no . . 3_656 C6 S2 C3 S2 0.08(17) no . . 3_656 C6 S2 C3 C2 -179.92(16) no . . . C6 O2 C7 C7 42.7(5) no . . 3_656 C7 O2 C6 S2 165.0(4) no . . . C7 O2 C6 C6 -14.8(6) no . . 3_656 S1 C2 C3 S2 -0.65(5) no . . . S1 C2 C3 S2 179.35(5) no . . 3_656 S1 C2 C3 S2 179.35(5) no 3_656 . . S1 C2 C3 S2 -0.65(5) no 3_656 . 3_656 S1 C4 C4 S1 2.4(5) no . 3_656 3_656 S1 C4 C4 C9 -178.2(3) no . 3_656 3_656 S1 C4 C9 C5 179.2(3) no . . . C4 C4 C9 C5 -0.2(6) no 3_656 . . C9 C4 C4 S1 -178.2(3) no . 3_656 3_656 C9 C4 C4 C9 1.2(6) no . 3_656 3_656 O8 C5 C5 O8 -1.0(7) no . 3_656 3_656 O8 C5 C5 C9 -179.1(4) no . 3_656 3_656 O8 C5 C9 C4 -179.8(4) no . . . C5 C5 C9 C4 -1.9(7) no 3_656 . . C9 C5 C5 O8 -179.1(4) no . 3_656 3_656 C9 C5 C5 C9 2.9(7) no . 3_656 3_656 S2 C6 C6 S2 0.4(6) no . 3_656 3_656 S2 C6 C6 O2 -179.8(3) no . 3_656 3_656 O2 C6 C6 S2 -179.8(4) no . 3_656 3_656 O2 C6 C6 O2 -0.0(8) no . 3_656 3_656 O2 C7 C7 O2 -60.0(6) no . 3_656 3_656