#------------------------------------------------------------------------------ #$Date: 2020-03-04 09:42:47 +0200 (Wed, 04 Mar 2020) $ #$Revision: 248750 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/74/1557446.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_1557446 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_paper_doi 10.1039/C9SC05902D _journal_volume 11 _journal_year 2020 _chemical_formula_moiety 'C20 H14 S4' _chemical_formula_sum 'C20 H14 S4' _chemical_formula_weight 382.55 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2017/1 _audit_update_record ; 2019-02-26 deposited with the CCDC. 2019-12-16 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90.980(2) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 7.45474(15) _cell_length_b 16.2651(3) _cell_length_c 6.76866(16) _cell_measurement_reflns_used 23973 _cell_measurement_temperature 90 _cell_measurement_theta_max 41.0760 _cell_measurement_theta_min 2.4710 _cell_volume 820.59(3) _computing_cell_refinement 'CrysAlisPro 1.171.39.9f (Rigaku OD, 2015)' _computing_data_collection CrystalClear _computing_data_reduction 'CrysAlisPro 1.171.39.9f (Rigaku OD, 2015)' _computing_molecular_graphics SHELXLE _computing_publication_material 'SHELXL-2017/1 (Sheldrick, 2017)' _computing_structure_refinement 'SHELXL-2017/1 (Sheldrick, 2017)' _computing_structure_solution SHELXT _diffrn_ambient_temperature 90 _diffrn_detector_area_resol_mean 7.31 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.977 _diffrn_measurement_device_type 'Rigaku AFC-8 with Saturn70 CCD' _diffrn_measurement_method \w-scan _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0849 _diffrn_reflns_av_unetI/netI 0.0361 _diffrn_reflns_Laue_measured_fraction_full 0.995 _diffrn_reflns_Laue_measured_fraction_max 0.977 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 49660 _diffrn_reflns_point_group_measured_fraction_full 0.995 _diffrn_reflns_point_group_measured_fraction_max 0.977 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 41.067 _diffrn_reflns_theta_min 2.504 _diffrn_source 'Fine-focus rotating anode' _exptl_absorpt_coefficient_mu 0.577 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.96207 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.9f (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'dark orange' _exptl_crystal_density_diffrn 1.548 _exptl_crystal_description block _exptl_crystal_F_000 396 _exptl_crystal_size_max 0.168 _exptl_crystal_size_mid 0.073 _exptl_crystal_size_min 0.043 _refine_diff_density_max 0.651 _refine_diff_density_min -0.329 _refine_diff_density_rms 0.101 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 137 _refine_ls_number_reflns 5309 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.076 _refine_ls_R_factor_all 0.0451 _refine_ls_R_factor_gt 0.0358 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0585P)^2^+0.0048P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0954 _refine_ls_wR_factor_ref 0.0999 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4403 _reflns_number_total 5309 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9sc05902d2.cif _cod_data_source_block 171012_beta-MT-ADT _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 1557446 _shelx_shelxl_version_number 2017/1 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_min 0.909 _shelx_estimated_absorpt_t_max 0.976 _shelx_res_file ; TITL beta-MT-ADT 171012_beta-MT-ADT.res created by SHELXL-2017/1 at 16:25:58 on 13-Oct-2017 CELL 0.71073 7.45474 16.2651 6.76866 90 90.980 90 ZERR 2 0.00015 0.0003 0.00016 0 0.002 0 LATT 1 SYMM -x, 1/2+y, 1/2-z SFAC C H S UNIT 40 28 8 L.S. 10 LIST 4 FMAP 2 PLAN 10 TEMP -183 SIZE 0.168 0.073 0.043 BOND $H CONF ACTA WGHT 0.058500 0.004800 FVAR 4.24314 S1 3 0.367763 0.688820 -0.147136 11.00000 0.01570 0.02118 = 0.01849 0.00442 -0.00034 0.00079 S2 3 0.925750 0.621952 -0.195461 11.00000 0.01614 0.02159 = 0.01842 0.00308 0.00301 0.00102 C1 1 0.683799 0.480408 0.489017 11.00000 0.01509 0.01838 = 0.01586 0.00103 0.00186 0.00182 H1 2 0.827092 0.471820 0.490481 11.00000 0.00601 C2 1 0.603015 0.528507 0.339837 11.00000 0.01523 0.01599 = 0.01405 -0.00006 0.00121 0.00069 C3 1 0.704201 0.557079 0.176986 11.00000 0.01545 0.01726 = 0.01556 0.00118 0.00224 0.00117 H3 2 0.822663 0.543825 0.164243 11.00000 0.02378 C4 1 0.622733 0.604646 0.033254 11.00000 0.01571 0.01529 = 0.01528 -0.00013 0.00146 -0.00019 C5 1 0.700776 0.640100 -0.142452 11.00000 0.01581 0.01747 = 0.01641 0.00116 0.00147 -0.00070 C6 1 0.580797 0.685852 -0.248396 11.00000 0.01735 0.02148 = 0.01781 0.00386 0.00075 -0.00048 H6 2 0.594867 0.710567 -0.364455 11.00000 0.03034 C7 1 0.436747 0.625626 0.048228 11.00000 0.01550 0.01611 = 0.01551 0.00078 0.00037 -0.00003 C8 1 0.334089 0.598422 0.201391 11.00000 0.01479 0.01768 = 0.01614 0.00097 0.00077 0.00105 H8 2 0.217152 0.605395 0.213156 11.00000 0.03009 C9 1 0.415679 0.548988 0.351118 11.00000 0.01493 0.01595 = 0.01456 -0.00025 0.00115 0.00043 C10 1 0.950628 0.685058 -0.411238 11.00000 0.02060 0.03134 = 0.02155 0.00706 0.00291 -0.00110 H10A 2 1.060902 0.677215 -0.439175 11.00000 0.03687 H10B 2 0.924241 0.738343 -0.379370 11.00000 0.02863 H10C 2 0.871314 0.665508 -0.504029 11.00000 0.03946 HKLF 4 REM beta-MT-ADT REM R1 = 0.0358 for 4403 Fo > 4sig(Fo) and 0.0451 for all 5309 data REM 137 parameters refined using 0 restraints END WGHT 0.0585 0.0048 REM Highest difference peak 0.651, deepest hole -0.329, 1-sigma level 0.101 Q1 1 0.3822 0.6098 0.1269 11.00000 0.05 0.65 Q2 1 0.6405 0.5028 0.4062 11.00000 0.05 0.64 Q3 1 0.3725 0.5749 0.2759 11.00000 0.05 0.63 Q4 1 0.5244 0.6157 0.0369 11.00000 0.05 0.58 Q5 1 0.6677 0.5798 0.0950 11.00000 0.05 0.57 Q6 1 0.9581 0.6523 -0.1503 11.00000 0.05 0.57 Q7 1 0.3748 0.5341 0.4361 11.00000 0.05 0.56 Q8 1 0.6370 0.6623 -0.1887 11.00000 0.05 0.56 Q9 1 0.4375 0.6808 -0.1791 11.00000 0.05 0.56 Q10 1 0.6600 0.5471 0.2612 11.00000 0.05 0.53 ; _shelx_res_checksum 75410 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.36776(3) 0.68882(2) -0.14714(3) 0.01846(5) Uani 1 1 d . . . . . S2 S 0.92575(3) 0.62195(2) -0.19546(3) 0.01869(5) Uani 1 1 d . . . . . C1 C 0.68380(11) 0.48041(5) 0.48902(11) 0.01643(11) Uani 1 1 d . . . . . H1 H 0.8271(17) 0.4718(7) 0.4905(17) 0.006(2) Uiso 1 1 d . . . . . C2 C 0.60302(10) 0.52851(4) 0.33984(11) 0.01508(11) Uani 1 1 d . . . . . C3 C 0.70420(10) 0.55708(5) 0.17699(11) 0.01607(11) Uani 1 1 d . . . . . H3 H 0.823(2) 0.5438(9) 0.164(2) 0.024(4) Uiso 1 1 d . . . . . C4 C 0.62273(10) 0.60465(4) 0.03325(11) 0.01541(11) Uani 1 1 d . . . . . C5 C 0.70078(11) 0.64010(5) -0.14245(12) 0.01655(11) Uani 1 1 d . . . . . C6 C 0.58080(12) 0.68585(5) -0.24840(13) 0.01887(13) Uani 1 1 d . . . . . H6 H 0.595(2) 0.7106(11) -0.364(2) 0.030(4) Uiso 1 1 d . . . . . C7 C 0.43675(10) 0.62563(5) 0.04823(11) 0.01571(11) Uani 1 1 d . . . . . C8 C 0.33409(11) 0.59842(5) 0.20139(11) 0.01620(11) Uani 1 1 d . . . . . H8 H 0.217(2) 0.6054(10) 0.213(3) 0.030(4) Uiso 1 1 d . . . . . C9 C 0.41568(10) 0.54899(4) 0.35112(11) 0.01514(11) Uani 1 1 d . . . . . C10 C 0.95063(14) 0.68506(7) -0.41124(15) 0.02446(16) Uani 1 1 d . . . . . H10A H 1.061(3) 0.6772(11) -0.439(3) 0.037(5) Uiso 1 1 d . . . . . H10B H 0.924(2) 0.7383(11) -0.379(2) 0.029(4) Uiso 1 1 d . . . . . H10C H 0.871(3) 0.6655(12) -0.504(3) 0.039(5) Uiso 1 1 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_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.01570(8) 0.02118(8) 0.01849(9) 0.00442(6) -0.00034(6) 0.00079(6) S2 0.01614(8) 0.02159(9) 0.01842(9) 0.00308(6) 0.00301(6) 0.00102(6) C1 0.0151(3) 0.0184(3) 0.0159(3) 0.0010(2) 0.0019(2) 0.0018(2) C2 0.0152(3) 0.0160(2) 0.0141(2) -0.00006(19) 0.0012(2) 0.00069(19) C3 0.0154(3) 0.0173(3) 0.0156(3) 0.0012(2) 0.0022(2) 0.0012(2) C4 0.0157(3) 0.0153(2) 0.0153(3) -0.00013(19) 0.0015(2) -0.0002(2) C5 0.0158(3) 0.0175(3) 0.0164(3) 0.0012(2) 0.0015(2) -0.0007(2) C6 0.0173(3) 0.0215(3) 0.0178(3) 0.0039(2) 0.0008(2) -0.0005(2) C7 0.0155(3) 0.0161(2) 0.0155(3) 0.0008(2) 0.0004(2) 0.0000(2) C8 0.0148(3) 0.0177(3) 0.0161(3) 0.0010(2) 0.0008(2) 0.0010(2) C9 0.0149(2) 0.0160(2) 0.0146(2) -0.00025(19) 0.00115(19) 0.00043(19) C10 0.0206(3) 0.0313(4) 0.0215(4) 0.0071(3) 0.0029(3) -0.0011(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' 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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 S1 C7 91.32(4) . . ? C5 S2 C10 100.56(4) . . ? C2 C1 C9 121.15(7) . 3_666 ? C2 C1 H1 119.5(6) . . ? C9 C1 H1 119.0(6) 3_666 . ? C1 C2 C3 120.78(7) . . ? C1 C2 C9 119.69(7) . . ? C3 C2 C9 119.53(7) . . ? C4 C3 C2 119.83(7) . . ? C4 C3 H3 118.8(9) . . ? C2 C3 H3 121.4(9) . . ? C3 C4 C7 119.98(7) . . ? C3 C4 C5 128.61(7) . . ? C7 C4 C5 111.41(7) . . ? C6 C5 C4 112.36(7) . . ? C6 C5 S2 127.59(6) . . ? C4 C5 S2 120.05(6) . . ? C5 C6 S1 113.83(6) . . ? C5 C6 H6 128.8(11) . . ? S1 C6 H6 117.2(11) . . ? C8 C7 C4 121.96(7) . . ? C8 C7 S1 126.97(6) . . ? C4 C7 S1 111.07(5) . . ? C7 C8 C9 118.91(7) . . ? C7 C8 H8 126.2(11) . . ? C9 C8 H8 114.8(11) . . ? C1 C9 C8 121.06(7) 3_666 . ? C1 C9 C2 119.16(7) 3_666 . ? C8 C9 C2 119.78(7) . . ? S2 C10 H10A 102.0(12) . . ? S2 C10 H10B 108.9(10) . . ? H10A C10 H10B 113.8(15) . . ? S2 C10 H10C 106.6(12) . . ? H10A C10 H10C 114.2(17) . . ? H10B C10 H10C 110.7(15) . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C6 1.7411(9) . ? S1 C7 1.7454(8) . ? S2 C5 1.7462(8) . ? S2 C10 1.7973(9) . ? C1 C2 1.4048(11) . ? C1 C9 1.4060(11) 3_666 ? C1 H1 1.077(13) . ? C2 C3 1.4242(10) . ? C2 C9 1.4390(11) . ? C3 C4 1.3761(11) . ? C3 H3 0.915(16) . ? C4 C7 1.4331(11) . ? C4 C5 1.4523(11) . ? C5 C6 1.3587(12) . ? C6 H6 0.890(17) . ? C7 C8 1.3724(11) . ? C8 C9 1.4221(11) . ? C8 H8 0.884(18) . ? C10 H10A 0.86(2) . ? C10 H10B 0.915(17) . ? C10 H10C 0.912(19) . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 C1 C2 C3 -179.12(7) 3_666 . . . ? C9 C1 C2 C9 0.67(12) 3_666 . . . ? C1 C2 C3 C4 -179.50(7) . . . . ? C9 C2 C3 C4 0.70(11) . . . . ? C2 C3 C4 C7 0.30(11) . . . . ? C2 C3 C4 C5 179.63(7) . . . . ? C3 C4 C5 C6 -178.14(8) . . . . ? C7 C4 C5 C6 1.23(10) . . . . ? C3 C4 C5 S2 1.58(12) . . . . ? C7 C4 C5 S2 -179.05(6) . . . . ? C10 S2 C5 C6 3.72(9) . . . . ? C10 S2 C5 C4 -175.96(7) . . . . ? C4 C5 C6 S1 -0.53(10) . . . . ? S2 C5 C6 S1 179.77(5) . . . . ? C7 S1 C6 C5 -0.23(7) . . . . ? C3 C4 C7 C8 -1.18(12) . . . . ? C5 C4 C7 C8 179.39(7) . . . . ? C3 C4 C7 S1 178.06(6) . . . . ? C5 C4 C7 S1 -1.37(8) . . . . ? C6 S1 C7 C8 -179.89(8) . . . . ? C6 S1 C7 C4 0.92(6) . . . . ? C4 C7 C8 C9 0.98(12) . . . . ? S1 C7 C8 C9 -178.13(6) . . . . ? C7 C8 C9 C1 -179.98(7) . . . 3_666 ? C7 C8 C9 C2 0.05(11) . . . . ? C1 C2 C9 C1 -0.66(12) . . . 3_666 ? C3 C2 C9 C1 179.14(7) . . . 3_666 ? C1 C2 C9 C8 179.31(7) . . . . ? C3 C2 C9 C8 -0.89(11) . . . . ?