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#$Date: 2025-08-22 18:52:37 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301865 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/11/7221154.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_7221154
loop_
_publ_author_name
'Hasegawa, Tsukasa'
'Ashizawa, Minoru'
'Matsumoto, Hidetoshi'
_publ_section_title
;
 Design and Structure-Property Relationship of Benzothienoisoindigo in
 Organic Field Effect Transistors
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA07660A
_journal_year                    2015
_chemical_formula_moiety         'C24 H30 N2 O2 S2'
_chemical_formula_sum            'C24 H30 N2 O2 S2'
_chemical_formula_weight         442.63
_space_group_IT_number           14
_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
;
2015-04-27 deposited with the CCDC.
2015-07-09 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 114.8240
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   19.2970(3)
_cell_length_b                   8.24241(10)
_cell_length_c                   15.6572(2)
_cell_measurement_reflns_used    23254
_cell_measurement_temperature    173
_cell_measurement_theta_max      68.22
_cell_measurement_theta_min      3.08
_cell_volume                     2260.23(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    'Il Milione (Burla, et al., 2007)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0782
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            25324
_diffrn_reflns_theta_full        68.22
_diffrn_reflns_theta_max         68.22
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.313
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            unknown
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       unknown
_exptl_crystal_F_000             944.00
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.210
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4124
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0399
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0648P)²+0.4334P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1094
_reflns_number_gt                3862
_reflns_number_total             4124
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            c5ra07660a2.cif
_cod_data_source_block           2
_cod_original_cell_volume        2260.24(6)
_cod_database_code               7221154
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
S1 S 0.813820(19) 0.00272(4) 0.92059(3) 0.02912(13) Uani 1.0 4 d .
S2 S 0.665425(19) 0.18922(4) 0.58789(2) 0.02681(13) Uani 1.0 4 d .
O1 O 1.07387(6) -0.06654(13) 0.89444(7) 0.0322(3) Uani 1.0 4 d .
O2 O 0.42507(5) -0.07389(12) 0.32003(7) 0.0291(3) Uani 1.0 4 d .
N4 N 0.94461(7) -0.08843(15) 0.79849(8) 0.0274(3) Uani 1.0 4 d .
N48 N 0.53555(7) 0.05883(15) 0.33601(8) 0.0263(3) Uani 1.0 4 d .
C1 C 0.75863(8) -0.0445(2) 0.80504(11) 0.0342(4) Uani 1.0 4 d .
C2 C 0.79940(8) -0.07907(18) 0.75387(11) 0.0317(4) Uani 1.0 4 d .
C3 C 0.87783(8) -0.06593(16) 0.81185(10) 0.0256(3) Uani 1.0 4 d .
C4 C 0.89557(8) -0.02229(16) 0.90364(10) 0.0237(3) Uani 1.0 4 d .
C5 C 0.97667(8) -0.01647(15) 0.95406(10) 0.0218(3) Uani 1.0 4 d .
C6 C 1.00703(8) -0.05902(16) 0.88205(10) 0.0247(3) Uani 1.0 4 d .
C7 C 0.94691(9) -0.14048(18) 0.71060(10) 0.0308(4) Uani 1.0 4 d .
C8 C 0.91720(10) -0.01261(17) 0.63358(11) 0.0320(4) Uani 1.0 4 d .
C9 C 0.90949(9) -0.07765(18) 0.53918(10) 0.0317(4) Uani 1.0 4 d .
C10 C 0.87952(9) 0.04734(19) 0.46032(11) 0.0330(4) Uani 1.0 4 d .
C11 C 0.86833(11) -0.0187(2) 0.36494(12) 0.0375(4) Uani 1.0 4 d .
C12 C 0.83854(12) 0.1057(3) 0.28632(12) 0.0498(5) Uani 1.0 4 d .
C13 C 0.70722(8) 0.24549(18) 0.51499(11) 0.0310(4) Uani 1.0 4 d .
C14 C 0.66513(8) 0.20652(18) 0.42185(11) 0.0297(4) Uani 1.0 4 d .
C15 C 0.59738(8) 0.12849(17) 0.41175(10) 0.0252(3) Uani 1.0 4 d .
C16 C 0.58818(8) 0.11002(16) 0.49418(10) 0.0231(3) Uani 1.0 4 d .
C17 C 0.51806(8) 0.02568(16) 0.47303(10) 0.0219(3) Uani 1.0 4 d .
C18 C 0.48535(8) -0.00521(16) 0.36859(10) 0.0234(3) Uani 1.0 4 d .
C19 C 0.52664(8) 0.04856(19) 0.23879(10) 0.0284(4) Uani 1.0 4 d .
C20 C 0.58360(8) -0.06542(18) 0.22604(10) 0.0273(4) Uani 1.0 4 d .
C21 C 0.57104(8) -0.07218(17) 0.12311(10) 0.0261(3) Uani 1.0 4 d .
C22 C 0.63406(8) -0.16169(18) 0.10819(10) 0.0273(3) Uani 1.0 4 d .
C23 C 0.62431(9) -0.15825(18) 0.00612(10) 0.0300(4) Uani 1.0 4 d .
C24 C 0.69019(10) -0.2402(3) -0.00679(12) 0.0394(4) Uani 1.0 4 d .
H1 H 0.7056 -0.0464 0.7794 0.0410 Uiso 1.0 4 calc R
H2 H 0.7784 -0.1070 0.6905 0.0380 Uiso 1.0 4 calc R
H3A H 0.9166 -0.2382 0.6887 0.0370 Uiso 1.0 4 calc R
H4B H 0.9992 -0.1670 0.7226 0.0370 Uiso 1.0 4 calc R
H5B H 0.8678 0.0253 0.6276 0.0384 Uiso 1.0 4 calc R
H6A H 0.9518 0.0792 0.6513 0.0384 Uiso 1.0 4 calc R
H7A H 0.8752 -0.1700 0.5220 0.0380 Uiso 1.0 4 calc R
H8B H 0.9590 -0.1155 0.5456 0.0380 Uiso 1.0 4 calc R
H9A H 0.8311 0.0888 0.4560 0.0396 Uiso 1.0 4 calc R
H10B H 0.9150 0.1375 0.4763 0.0396 Uiso 1.0 4 calc R
H11B H 0.8328 -0.1088 0.3489 0.0450 Uiso 1.0 4 calc R
H12A H 0.9167 -0.0602 0.3693 0.0450 Uiso 1.0 4 calc R
H13B H 0.7901 0.1460 0.2804 0.0598 Uiso 1.0 4 calc R
H14C H 0.8326 0.0559 0.2282 0.0598 Uiso 1.0 4 calc R
H15A H 0.8741 0.1940 0.3005 0.0598 Uiso 1.0 4 calc R
H16 H 0.7542 0.2978 0.5365 0.0371 Uiso 1.0 4 calc R
H17 H 0.6793 0.2284 0.3731 0.0356 Uiso 1.0 4 calc R
H18A H 0.5326 0.1561 0.2176 0.0340 Uiso 1.0 4 calc R
H19B H 0.4753 0.0117 0.1993 0.0340 Uiso 1.0 4 calc R
H20B H 0.5780 -0.1734 0.2470 0.0328 Uiso 1.0 4 calc R
H21A H 0.6351 -0.0284 0.2644 0.0328 Uiso 1.0 4 calc R
H22B H 0.5227 -0.1254 0.0867 0.0313 Uiso 1.0 4 calc R
H23A H 0.5677 0.0377 0.0995 0.0313 Uiso 1.0 4 calc R
H24B H 0.6350 -0.2737 0.1277 0.0327 Uiso 1.0 4 calc R
H25A H 0.6828 -0.1132 0.1480 0.0327 Uiso 1.0 4 calc R
H26B H 0.5770 -0.2124 -0.0333 0.0360 Uiso 1.0 4 calc R
H27A H 0.6205 -0.0464 -0.0146 0.0360 Uiso 1.0 4 calc R
H28A H 0.7370 -0.1852 0.0307 0.0473 Uiso 1.0 4 calc R
H29C H 0.6812 -0.2353 -0.0719 0.0473 Uiso 1.0 4 calc R
H30B H 0.6937 -0.3514 0.0127 0.0473 Uiso 1.0 4 calc R
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)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 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_3
C1 S1 C4 90.78(8) yes . .
C13 S2 C16 90.93(8) yes . .
C3 N4 C6 109.09(14) yes . .
C3 N4 C7 124.97(11) yes . .
C6 N4 C7 125.90(15) yes . .
C15 N48 C18 108.95(13) yes . .
C15 N48 C19 126.18(15) yes . .
C18 N48 C19 124.82(11) yes . .
S1 C1 C2 114.21(11) yes . .
C1 C2 C3 109.51(14) yes . .
N4 C3 C2 134.58(15) yes . .
N4 C3 C4 110.41(12) yes . .
C2 C3 C4 115.00(16) yes . .
S1 C4 C3 110.50(11) yes . .
S1 C4 C5 140.81(13) yes . .
C3 C4 C5 108.68(16) yes . .
C4 C5 C5 132.37(17) yes . 3_757
C4 C5 C6 104.93(12) yes . .
C5 C5 C6 122.70(14) yes 3_757 .
O1 C6 N4 125.82(16) yes . .
O1 C6 C5 127.29(12) yes . .
N4 C6 C5 106.89(13) yes . .
N4 C7 C8 113.16(14) yes . .
C7 C8 C9 112.15(13) yes . .
C8 C9 C10 113.49(13) yes . .
C9 C10 C11 113.83(14) yes . .
C10 C11 C12 113.90(15) yes . .
S2 C13 C14 114.13(12) yes . .
C13 C14 C15 109.47(17) yes . .
N48 C15 C14 134.65(16) yes . .
N48 C15 C16 110.28(14) yes . .
C14 C15 C16 115.04(13) yes . .
S2 C16 C15 110.43(12) yes . .
S2 C16 C17 141.04(14) yes . .
C15 C16 C17 108.48(12) yes . .
C16 C17 C17 133.21(13) yes . 3_656
C16 C17 C18 104.94(15) yes . .
C17 C17 C18 121.85(13) yes 3_656 .
O2 C18 N48 125.35(15) yes . .
O2 C18 C17 127.30(16) yes . .
N48 C18 C17 107.35(12) yes . .
N48 C19 C20 113.39(11) yes . .
C19 C20 C21 110.96(11) yes . .
C20 C21 C22 113.37(11) yes . .
C21 C22 C23 113.32(12) yes . .
C22 C23 C24 112.74(12) yes . .
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 C1 1.7149(15) yes .
S1 C4 1.7184(18) yes .
S2 C13 1.715(2) yes .
S2 C16 1.7217(13) yes .
O1 C6 1.223(2) yes .
O2 C18 1.2284(16) yes .
N4 C3 1.402(3) yes .
N4 C6 1.3777(16) yes .
N4 C7 1.460(3) yes .
N48 C15 1.4041(16) yes .
N48 C18 1.376(3) yes .
N48 C19 1.461(2) yes .
C1 C2 1.368(3) yes .
C2 C3 1.4046(19) yes .
C3 C4 1.378(3) yes .
C4 C5 1.4273(19) yes .
C5 C5 1.3661(19) yes 3_757
C5 C6 1.514(3) yes .
C7 C8 1.521(2) yes .
C8 C9 1.520(3) yes .
C9 C10 1.523(2) yes .
C10 C11 1.517(3) yes .
C11 C12 1.517(3) yes .
C13 C14 1.377(2) yes .
C14 C15 1.405(3) yes .
C15 C16 1.383(3) yes .
C16 C17 1.431(2) yes .
C17 C17 1.368(3) yes 3_656
C17 C18 1.507(2) yes .
C19 C20 1.521(3) yes .
C20 C21 1.527(3) yes .
C21 C22 1.522(3) yes .
C22 C23 1.529(3) yes .
C23 C24 1.526(3) yes .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139200538
