#------------------------------------------------------------------------------
#$Date: 2019-11-24 20:56:17 +0200 (Sun, 24 Nov 2019) $
#$Revision: 239395 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/65/4516595.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_4516595
loop_
_publ_author_name
'Yoo, Dongho'
'Luo, Xuyi'
'Hasegawa, Tsukasa'
'Ashizawa, Minoru'
'Kawamoto, Tadashi'
'Masunaga, Hiroyasu'
'Ohta, Noboru'
'Matsumoto, Hidetoshi'
'Mei, Jianguo'
'Mori, Takehiko'
_publ_section_title
;
 n-Type Organic Field-Effect Transistors Based on Bisthienoisatin
 Derivatives
;
_journal_issue                   5
_journal_name_full               'ACS Applied Electronic Materials'
_journal_page_first              764
_journal_paper_doi               10.1021/acsaelm.9b00105
_journal_volume                  1
_journal_year                    2019
_chemical_formula_moiety         'C24 H28 N2 O4 S2'
_chemical_formula_sum            'C24 H28 N2 O4 S2'
_chemical_formula_weight         472.62
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 111.402(3)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   33.028(3)
_cell_length_b                   5.02936(18)
_cell_length_c                   14.9494(5)
_cell_measurement_reflns_used    698
_cell_measurement_temperature    171
_cell_measurement_theta_max      72.08
_cell_measurement_theta_min      5.95
_cell_volume                     2312.0(2)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.2.2'
_computing_publication_material  'CrystalStructure 4.2.2 (Rigaku, 2016)'
_computing_structure_refinement  'SHELXL Version 2016/6 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      171
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12385
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.244
_diffrn_reflns_theta_min         5.755
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.366
_exptl_absorpt_correction_T_max  0.954
_exptl_absorpt_correction_T_min  0.752
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1000.00
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.41
_refine_diff_density_min         -0.25
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2079
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0562
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0950P)²+0.6787P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1505
_refine_ls_wR_factor_ref         0.1560
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1699
_reflns_number_total             2079
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            el9b00105_si_002.cif
_cod_data_source_block           BTI-Hex
_cod_database_code               4516595
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
S1 S 0.49292(2) 0.83981(11) 0.35929(4) 0.0363(3) Uani 1 1 d . .
O1 O 0.38071(6) 0.0562(4) 0.26074(13) 0.0514(5) Uani 1 1 d . .
O2 O 0.43720(7) 0.3540(3) 0.18147(12) 0.0504(5) Uani 1 1 d . .
N1 N 0.40778(7) 0.3566(4) 0.38607(14) 0.0357(5) Uani 1 1 d . .
C1 C 0.40323(9) 0.2425(5) 0.29851(18) 0.0394(6) Uani 1 1 d . .
C2 C 0.43437(8) 0.4013(5) 0.25878(17) 0.0392(6) Uani 1 1 d . .
C3 C 0.45512(8) 0.5913(5) 0.33357(16) 0.0354(6) Uani 1 1 d . .
C4 C 0.43887(8) 0.5574(5) 0.40630(15) 0.0324(5) Uani 1 1 d . .
C5 C 0.45703(8) 0.7289(5) 0.48437(16) 0.0321(5) Uani 1 1 d . .
H5 H 0.449766 0.730817 0.540274 0.039 Uiso 1 1 calc R U
C6 C 0.48722(8) 0.8961(4) 0.46851(15) 0.0319(5) Uani 1 1 d . .
C7 C 0.38692(9) 0.2563(5) 0.45076(18) 0.0400(6) Uani 1 1 d . .
H7A H 0.409805 0.211473 0.513264 0.048 Uiso 1 1 calc R U
H7B H 0.371176 0.090251 0.423412 0.048 Uiso 1 1 calc R U
C8 C 0.35546(8) 0.4482(5) 0.46812(18) 0.0419(6) Uani 1 1 d . .
H8A H 0.331916 0.490909 0.406321 0.050 Uiso 1 1 calc R U
H8B H 0.370798 0.615493 0.495456 0.050 Uiso 1 1 calc R U
C9 C 0.33589(9) 0.3288(5) 0.5372(2) 0.0459(7) Uani 1 1 d . .
H9A H 0.316846 0.178379 0.504823 0.055 Uiso 1 1 calc R U
H9B H 0.359734 0.256546 0.593703 0.055 Uiso 1 1 calc R U
C10 C 0.30987(9) 0.5219(6) 0.57171(19) 0.0480(7) Uani 1 1 d . .
H10A H 0.284267 0.579839 0.515973 0.058 Uiso 1 1 calc R U
H10B H 0.327951 0.681047 0.597996 0.058 Uiso 1 1 calc R U
C11 C 0.29425(11) 0.4107(6) 0.6480(2) 0.0580(8) Uani 1 1 d . .
H11A H 0.274198 0.260582 0.620318 0.070 Uiso 1 1 calc R U
H11B H 0.319543 0.340409 0.701886 0.070 Uiso 1 1 calc R U
C12 C 0.27125(12) 0.6146(7) 0.6866(3) 0.0659(9) Uani 1 1 d . .
H12A H 0.261952 0.532030 0.735316 0.079 Uiso 1 1 calc R U
H12B H 0.291118 0.762052 0.715566 0.079 Uiso 1 1 calc R U
H12C H 0.245749 0.682181 0.633952 0.079 Uiso 1 1 calc R U
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
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.3331 0.5567
;
International Tables for Crystallography
(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
C3 S1 C6 90.56(11) . .
C1 N1 C4 108.8(2) . .
C1 N1 C7 124.4(2) . .
C4 N1 C7 126.4(2) . .
O1 C1 N1 127.0(2) . .
O1 C1 C2 126.4(2) . .
N1 C1 C2 106.6(2) . .
O2 C2 C3 133.4(3) . .
O2 C2 C1 123.0(2) . .
C3 C2 C1 103.5(2) . .
C4 C3 C2 108.5(2) . .
C4 C3 S1 111.91(18) . .
C2 C3 S1 139.63(19) . .
C3 C4 N1 112.6(2) . .
C3 C4 C5 114.1(2) . .
N1 C4 C5 133.3(2) . .
C6 C5 C4 110.3(2) . .
C6 C5 H5 124.9 . .
C4 C5 H5 124.9 . .
C5 C6 C6 127.5(2) . 5_676
C5 C6 S1 113.16(17) . .
C6 C6 S1 119.4(2) 5_676 .
N1 C7 C8 114.4(2) . .
N1 C7 H7A 108.7 . .
C8 C7 H7A 108.7 . .
N1 C7 H7B 108.7 . .
C8 C7 H7B 108.7 . .
H7A C7 H7B 107.6 . .
C7 C8 C9 110.7(2) . .
C7 C8 H8A 109.5 . .
C9 C8 H8A 109.5 . .
C7 C8 H8B 109.5 . .
C9 C8 H8B 109.5 . .
H8A C8 H8B 108.1 . .
C10 C9 C8 114.4(2) . .
C10 C9 H9A 108.7 . .
C8 C9 H9A 108.7 . .
C10 C9 H9B 108.7 . .
C8 C9 H9B 108.7 . .
H9A C9 H9B 107.6 . .
C9 C10 C11 114.3(2) . .
C9 C10 H10A 108.7 . .
C11 C10 H10A 108.7 . .
C9 C10 H10B 108.7 . .
C11 C10 H10B 108.7 . .
H10A C10 H10B 107.6 . .
C12 C11 C10 113.1(2) . .
C12 C11 H11A 109.0 . .
C10 C11 H11A 109.0 . .
C12 C11 H11B 109.0 . .
C10 C11 H11B 109.0 . .
H11A C11 H11B 107.8 . .
C11 C12 H12A 109.5 . .
C11 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C11 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C3 1.709(3) .
S1 C6 1.734(2) .
O1 C1 1.201(3) .
O2 C2 1.217(3) .
N1 C1 1.386(3) .
N1 C4 1.393(3) .
N1 C7 1.466(3) .
C1 C2 1.579(4) .
C2 C3 1.440(3) .
C3 C4 1.387(3) .
C4 C5 1.398(3) .
C5 C6 1.389(3) .
C5 H5 0.9500 .
C6 C6 1.453(5) 5_676
C7 C8 1.508(3) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 C9 1.527(3) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 C10 1.507(4) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 C11 1.520(4) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 C12 1.510(4) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
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_4
C4 N1 C1 O1 176.5(3) .
C7 N1 C1 O1 3.4(4) .
C4 N1 C1 C2 -2.2(2) .
C7 N1 C1 C2 -175.3(2) .
O1 C1 C2 O2 3.1(4) .
N1 C1 C2 O2 -178.2(2) .
O1 C1 C2 C3 -176.8(3) .
N1 C1 C2 C3 1.9(3) .
O2 C2 C3 C4 179.3(3) .
C1 C2 C3 C4 -0.8(3) .
O2 C2 C3 S1 -0.9(5) .
C1 C2 C3 S1 179.0(2) .
C6 S1 C3 C4 0.52(19) .
C6 S1 C3 C2 -179.3(3) .
C2 C3 C4 N1 -0.5(3) .
S1 C3 C4 N1 179.59(16) .
C2 C3 C4 C5 179.1(2) .
S1 C3 C4 C5 -0.8(3) .
C1 N1 C4 C3 1.8(3) .
C7 N1 C4 C3 174.7(2) .
C1 N1 C4 C5 -177.7(3) .
C7 N1 C4 C5 -4.8(4) .
C3 C4 C5 C6 0.6(3) .
N1 C4 C5 C6 -179.8(2) .
C4 C5 C6 C6 179.3(3) 5_676
C4 C5 C6 S1 -0.2(3) .
C3 S1 C6 C5 -0.16(18) .
C3 S1 C6 C6 -179.7(3) 5_676
C1 N1 C7 C8 -117.8(3) .
C4 N1 C7 C8 70.4(3) .
N1 C7 C8 C9 -179.2(2) .
C7 C8 C9 C10 170.4(2) .
C8 C9 C10 C11 -174.1(3) .
C9 C10 C11 C12 175.6(3) .
