#------------------------------------------------------------------------------
#$Date: 2020-10-06 10:11:09 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257323 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/74/1557446.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 π-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         '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       ω-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/[σ²(Fo²)+(0.0585P)²+0.0048P] where P=(Fo²+2Fc²)/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 > 2σ(I)'
_cod_data_source_file            c9sc05902d2.cif
_cod_data_source_block           171012_beta-MT-ADT
_cod_depositor_comments
'Adding full bibliography for 1557445--1557447.cif.'
_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
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_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) . . . . ?
