#------------------------------------------------------------------------------ #$Date: 2020-10-06 10:11:09 +0300 (Tue, 06 Oct 2020) $ #$Revision: 257323 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/74/1557447.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_1557447 loop_ _publ_author_name 'Wang, Chengyuan' 'Hashizume, Daisuke' 'Nakano, Masahiro' 'Ogaki, Takuya' 'Takenaka, Hiroyuki' 'Kawabata, Kohsuke' 'Takimiya, Kazuo' _publ_section_title ; “Disrupt and induce” intermolecular interactions to rationally design organic semiconductor crystals: from herringbone to rubrene-like pitched \p-stacking ; _journal_issue 6 _journal_name_full 'Chemical Science' _journal_page_first 1573 _journal_page_last 1580 _journal_paper_doi 10.1039/C9SC05902D _journal_volume 11 _journal_year 2020 _chemical_formula_moiety 'C16 H12 S4' _chemical_formula_sum 'C16 H12 S4' _chemical_formula_weight 332.51 _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _symmetry_cell_setting monoclinic _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_update_record ; 2019-02-26 deposited with the CCDC. 2019-12-16 downloaded from the CCDC. ; _cell_angle_alpha 90.0000 _cell_angle_beta 91.180(3) _cell_angle_gamma 90.0000 _cell_formula_units_Z 2 _cell_length_a 7.6311(3) _cell_length_b 17.4783(7) _cell_length_c 5.2771(2) _cell_measurement_reflns_used 4675 _cell_measurement_temperature 100 _cell_measurement_theta_max 68.06 _cell_measurement_theta_min 5.06 _cell_volume 703.70(5) _computing_cell_refinement 'RAPID AUTO' _computing_data_collection 'RAPID AUTO (Rigaku, ????)' _computing_data_reduction 'RAPID AUTO' _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 100 _diffrn_detector_area_resol_mean 10.000 _diffrn_measured_fraction_theta_full 0.981 _diffrn_measured_fraction_theta_max 0.981 _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method \w _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54187 _diffrn_reflns_av_R_equivalents 0.1200 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_number 12203 _diffrn_reflns_theta_full 68.24 _diffrn_reflns_theta_max 68.24 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 6.058 _exptl_absorpt_correction_T_max 0.941 _exptl_absorpt_correction_T_min 0.663 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'ABSCOR (Rigaku, 1995)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.569 _exptl_crystal_density_method 'not measured' _exptl_crystal_description platelet _exptl_crystal_F_000 344.00 _exptl_crystal_size_max 0.600 _exptl_crystal_size_mid 0.300 _exptl_crystal_size_min 0.010 _refine_diff_density_max 1.070 _refine_diff_density_min -0.410 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.233 _refine_ls_hydrogen_treatment constr _refine_ls_number_parameters 91 _refine_ls_number_reflns 1262 _refine_ls_number_restraints 0 _refine_ls_R_factor_gt 0.0754 _refine_ls_shift/su_max 0.034 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.2144 _reflns_number_gt 946 _reflns_number_total 1262 _reflns_threshold_expression F^2^>2.0\s(F^2^) _cod_data_source_file c9sc05902d2.cif _cod_data_source_block 170331-Beta-MT-NDT1 _cod_depositor_comments 'Adding full bibliography for 1557445--1557447.cif.' _cod_database_code 1557447 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,1/2+Y,1/2-Z 3 -X,-Y,-Z 4 +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 _atom_site_disorder_assembly _atom_site_disorder_group S1 S 1.12842(18) 0.17124(6) 0.5456(3) 0.0402(5) Uani 1.0 4 d . . . S2 S 0.58028(18) 0.11465(6) 0.6161(3) 0.0419(6) Uani 1.0 4 d . . . C1 C 0.8060(7) 0.0284(3) 0.1929(9) 0.0363(12) Uani 1.0 4 d . . . C2 C 0.8825(7) 0.0832(3) 0.3519(9) 0.0361(12) Uani 1.0 4 d . . . C3 C 0.9076(7) -0.0096(3) 0.0091(10) 0.0361(12) Uani 1.0 4 d . . . C4 C 0.8016(7) 0.1269(3) 0.5490(10) 0.0370(13) Uani 1.0 4 d . . . C5 C 1.0633(7) 0.1008(3) 0.3247(10) 0.0375(12) Uani 1.0 4 d . . . C6 C 0.9190(7) 0.1750(3) 0.6654(11) 0.0403(13) Uani 1.0 4 d . . . C7 C 1.1682(7) 0.0650(3) 0.1538(10) 0.0389(13) Uani 1.0 4 d . . . C8 C 0.5521(8) 0.1801(3) 0.8738(11) 0.0449(14) Uani 1.0 4 d . . . H1 H 0.6852 0.0164 0.2076 0.0436 Uiso 1.0 4 calc R . . H6 H 0.8883 0.2078 0.8010 0.0484 Uiso 1.0 4 calc R . . H7 H 1.2892 0.0772 0.1450 0.0466 Uiso 1.0 4 calc R . . H8A H 0.4303 0.1783 0.9289 0.0539 Uiso 1.0 4 calc R . . H8B H 0.6305 0.1657 1.0153 0.0539 Uiso 1.0 4 calc R . . H8C H 0.5801 0.2321 0.8181 0.0539 Uiso 1.0 4 calc R . . 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 0.0518(10) 0.0236(8) 0.0449(10) -0.0002(5) -0.0034(7) -0.0022(5) S2 0.0523(10) 0.0284(8) 0.0451(10) 0.0004(5) 0.0015(7) -0.0029(5) C1 0.046(3) 0.025(3) 0.038(3) 0.000(2) -0.002(3) 0.006(2) C2 0.050(4) 0.022(3) 0.036(3) 0.002(2) -0.001(3) 0.005(2) C3 0.050(3) 0.021(3) 0.037(3) 0.002(2) -0.001(3) 0.0044(19) C4 0.050(4) 0.023(3) 0.038(3) -0.002(2) -0.001(3) 0.003(2) C5 0.055(4) 0.019(3) 0.037(3) -0.000(2) -0.006(3) 0.0011(19) C6 0.051(4) 0.025(3) 0.046(4) 0.004(2) -0.000(3) -0.000(2) C7 0.055(4) 0.020(3) 0.041(4) -0.001(2) -0.002(3) 0.007(2) C8 0.058(4) 0.030(3) 0.046(4) -0.001(3) 0.004(3) -0.005(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 ; 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) ; S S 0.3331 0.5567 ; International Tables for Crystallography (1992, 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C5 S1 C6 91.0(3) yes . . . C4 S2 C8 102.0(3) yes . . . C2 C1 C3 120.3(5) yes . . . C1 C2 C4 128.2(5) yes . . . C1 C2 C5 118.8(5) yes . . . C4 C2 C5 112.9(4) yes . . . C1 C3 C3 118.8(5) yes . . 3_755 C1 C3 C7 121.0(5) yes . . 3_755 C3 C3 C7 120.2(5) yes 3_755 . 3_755 S2 C4 C2 120.9(4) yes . . . S2 C4 C6 127.8(4) yes . . . C2 C4 C6 111.4(5) yes . . . S1 C5 C2 110.2(4) yes . . . S1 C5 C7 126.5(4) yes . . . C2 C5 C7 123.2(5) yes . . . S1 C6 C4 114.5(4) yes . . . C3 C7 C5 118.5(5) yes 3_755 . . C2 C1 H1 119.832 no . . . C3 C1 H1 119.831 no . . . S1 C6 H6 122.763 no . . . C4 C6 H6 122.765 no . . . C3 C7 H7 120.735 no 3_755 . . C5 C7 H7 120.733 no . . . S2 C8 H8A 109.474 no . . . S2 C8 H8B 109.468 no . . . S2 C8 H8C 109.471 no . . . H8A C8 H8B 109.473 no . . . H8A C8 H8C 109.471 no . . . H8B C8 H8C 109.470 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_1 _geom_bond_site_symmetry_2 S1 C5 1.760(5) yes . . S1 C6 1.732(6) yes . . S2 C4 1.746(6) yes . . S2 C8 1.794(6) yes . . C1 C2 1.394(7) yes . . C1 C3 1.419(7) yes . . C2 C4 1.439(7) yes . . C2 C5 1.424(8) yes . . C3 C3 1.454(7) yes . 3_755 C3 C7 1.411(7) yes . 3_755 C4 C6 1.365(7) yes . . C5 C7 1.369(7) yes . . C1 H1 0.950 no . . C6 H6 0.950 no . . C7 H7 0.950 no . . C8 H8A 0.980 no . . C8 H8B 0.980 no . . C8 H8C 0.980 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_1 _geom_contact_site_symmetry_2 S2 C1 3.223(5) no . . C1 C7 2.848(8) no . . C2 C3 2.825(7) no . 3_755 C3 C5 2.798(7) no . . C6 C8 3.030(8) no . . S1 S2 3.599(2) no . 1_655 S2 S1 3.599(2) no . 1_455 C1 C5 3.532(7) no . 3_756 C3 C4 3.487(7) no . 1_554 C4 C3 3.487(7) no . 1_556 C5 C1 3.532(7) no . 3_756 C8 C8 3.596(8) no . 4_554 C8 C8 3.596(8) no . 4_555 S1 H7 2.9635 no . . S2 H1 2.8821 no . . S2 H6 3.0054 no . . C1 H7 2.6573 no . 3_755 C2 H6 3.2173 no . . C2 H7 3.3125 no . . C3 H1 3.3351 no . 3_755 C3 H7 3.3480 no . . C4 H1 2.7741 no . . C4 H8B 2.8906 no . . C4 H8C 2.8906 no . . C5 H1 3.2881 no . . C5 H6 3.4254 no . . C6 H8B 2.9068 no . . C6 H8C 2.9016 no . . C7 H1 2.6460 no . 3_755 C8 H6 2.6466 no . . H1 H7 2.4886 no . 3_755 H6 H8B 2.4045 no . . H6 H8C 2.3936 no . . S1 H6 3.0656 no . 4_554 S1 H8A 3.0368 no . 1_655 S1 H8A 3.5585 no . 4_654 S2 H1 3.2087 no . 3_656 S2 H7 3.3635 no . 1_455 S2 H8B 3.3231 no . 1_554 S2 H8C 3.1062 no . 4_554 C1 H8B 2.8950 no . 1_554 C2 H8B 2.9652 no . 1_554 C4 H6 3.2463 no . 4_554 C4 H8B 3.1536 no . 1_554 C4 H8C 3.2148 no . 4_554 C5 H6 3.5724 no . 1_554 C6 H6 2.8170 no . 4_554 C6 H8C 3.5345 no . 4_554 C7 H8A 3.0704 no . 1_654 C8 H1 3.4997 no . 1_556 C8 H7 3.0703 no . 1_456 C8 H8A 3.5231 no . 4_554 C8 H8B 3.3533 no . 4_554 C8 H8C 3.3208 no . 4_554 C8 H8C 2.8063 no . 4_555 H1 S2 3.2087 no . 3_656 H1 C8 3.4997 no . 1_554 H1 H1 3.5871 no . 3_655 H1 H7 3.2140 no . 1_455 H1 H8A 3.5847 no . 3_656 H1 H8B 2.8279 no . 1_554 H6 S1 3.0656 no . 4_555 H6 C4 3.2463 no . 4_555 H6 C5 3.5724 no . 1_556 H6 C6 2.8170 no . 4_555 H6 H6 3.0234 no . 4_554 H6 H6 3.0234 no . 4_555 H6 H8B 3.3031 no . 4_554 H6 H8C 3.5896 no . 4_554 H7 S2 3.3635 no . 1_655 H7 C8 3.0703 no . 1_654 H7 H1 3.2140 no . 1_655 H7 H8A 2.3732 no . 1_654 H7 H8B 3.1175 no . 1_654 H8A S1 3.0368 no . 1_455 H8A S1 3.5585 no . 4_455 H8A C7 3.0704 no . 1_456 H8A C8 3.5231 no . 4_555 H8A H1 3.5847 no . 3_656 H8A H7 2.3732 no . 1_456 H8A H8C 2.8073 no . 4_555 H8B S2 3.3231 no . 1_556 H8B C1 2.8950 no . 1_556 H8B C2 2.9652 no . 1_556 H8B C4 3.1536 no . 1_556 H8B C8 3.3533 no . 4_555 H8B H1 2.8279 no . 1_556 H8B H6 3.3031 no . 4_555 H8B H7 3.1175 no . 1_456 H8B H8C 2.4321 no . 4_555 H8C S2 3.1062 no . 4_555 H8C C4 3.2148 no . 4_555 H8C C6 3.5345 no . 4_555 H8C C8 2.8063 no . 4_554 H8C C8 3.3208 no . 4_555 H8C H6 3.5896 no . 4_555 H8C H8A 2.8073 no . 4_554 H8C H8B 2.4321 no . 4_554 H8C H8C 2.7118 no . 4_554 H8C H8C 2.7118 no . 4_555 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_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C5 S1 C6 C4 -0.4(4) no . . . . C6 S1 C5 C2 0.2(3) no . . . . C6 S1 C5 C7 -177.9(4) no . . . . C8 S2 C4 C2 179.0(4) no . . . . C8 S2 C4 C6 -0.5(5) no . . . . C2 C1 C3 C3 0.2(7) no . . . 3_755 C2 C1 C3 C7 -179.8(4) no . . . 3_755 C3 C1 C2 C4 -179.5(4) no . . . . C3 C1 C2 C5 0.6(7) no . . . . C1 C2 C4 S2 0.1(7) no . . . . C1 C2 C4 C6 179.7(4) no . . . . C1 C2 C5 S1 -180.0(4) no . . . . C1 C2 C5 C7 -1.8(7) no . . . . C4 C2 C5 S1 0.1(5) no . . . . C4 C2 C5 C7 178.3(4) no . . . . C5 C2 C4 S2 -180.0(4) no . . . . C5 C2 C4 C6 -0.4(6) no . . . . C1 C3 C3 C1 180(427234) no . . 3_755 3_755 C1 C3 C3 C7 0.0(7) no . . 3_755 . C1 C3 C7 C5 -178.9(4) no . . 3_755 3_755 C3 C3 C7 C5 1.1(7) no 3_755 . 3_755 3_755 C7 C3 C3 C1 -0.0(7) no 3_755 . 3_755 3_755 C7 C3 C3 C7 180(427234) no 3_755 . 3_755 . S2 C4 C6 S1 -179.9(3) no . . . . C2 C4 C6 S1 0.5(6) no . . . . S1 C5 C7 C3 179.9(3) no . . . 3_755 C2 C5 C7 C3 2.1(7) no . . . 3_755