#------------------------------------------------------------------------------
#$Date: 2025-08-22 23:12:46 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301866 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/68/7236872.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_7236872
loop_
_publ_author_name
'Iijima, Kodai'
'Le Gal, Yann'
'Higashino, Toshiki'
'Lorcy, Dominique'
'Mori, Takehiko'
_publ_section_title
;
 Birhodanines and their sulfur analogues for air-stable n-channel organic
 transistors
;
_journal_issue                   35
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              9121
_journal_paper_doi               10.1039/C7TC02886E
_journal_volume                  5
_journal_year                    2017
_chemical_formula_moiety         'C8 H6 N2 O2 S4'
_chemical_formula_sum            'C8 H6 N2 O2 S4'
_chemical_formula_weight         290.39
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2017-06-27 deposited with the CCDC.
2017-08-16 downloaded from the CCDC.
;
_cell_angle_alpha                81.629(13)
_cell_angle_beta                 80.329(12)
_cell_angle_gamma                84.727(13)
_cell_formula_units_Z            1
_cell_length_a                   4.7328(5)
_cell_length_b                   5.6266(10)
_cell_length_c                   10.8786(16)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298
_cell_measurement_theta_max      16.99
_cell_measurement_theta_min      15.13
_cell_volume                     281.86(7)
_computing_cell_refinement       WinAFC
_computing_data_collection       WinAFC
_computing_data_reduction        WinAFC
_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      298
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku AFC7R'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0175
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2001
_diffrn_reflns_theta_full        29.98
_diffrn_reflns_theta_max         29.98
_diffrn_standards_decay_%        -0.136
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.826
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.948
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North, Phillips & Mathews, 1968)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.711
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             148.00
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.240
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     73
_refine_ls_number_reflns         1642
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0358
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0357P)²+0.0756P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0948
_reflns_number_gt                1086
_reflns_number_total             1642
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            c7tc02886e2.cif
_cod_data_source_block           KI28
_cod_original_cell_volume        281.86(8)
_cod_database_code               7236872
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,-Y,-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 0.87862(12) 0.35240(11) 0.38007(5) 0.04099(17) Uani 1.0 2 d .
S2 S 1.20557(14) 0.53366(13) 0.13174(6) 0.0541(3) Uani 1.0 2 d .
O1 O 0.3426(4) 0.9039(4) 0.38050(17) 0.0567(5) Uani 1.0 2 d .
N1 N 0.7462(5) 0.7622(4) 0.25393(18) 0.0396(5) Uani 1.0 2 d .
C1 C 0.5845(5) 0.5268(4) 0.44427(19) 0.0345(5) Uani 1.0 2 d .
C2 C 0.5358(5) 0.7524(5) 0.3604(2) 0.0397(5) Uani 1.0 2 d .
C3 C 0.9421(5) 0.5689(5) 0.2475(2) 0.0383(5) Uani 1.0 2 d .
C4 C 0.7442(7) 0.9647(5) 0.1533(3) 0.0544(7) Uani 1.0 2 d .
H4A H 0.7284 0.9066 0.0762 0.0652 Uiso 1.0 2 calc R
H4B H 0.9193 1.0441 0.1431 0.0652 Uiso 1.0 2 calc R
H4C H 0.5836 1.0763 0.1746 0.0652 Uiso 1.0 2 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 0.0360(3) 0.0445(4) 0.0368(3) 0.0068(3) 0.0039(3) -0.0038(3)
S2 0.0490(4) 0.0602(5) 0.0455(4) -0.0036(3) 0.0166(3) -0.0095(3)
O1 0.0547(11) 0.0510(11) 0.0510(11) 0.0165(9) 0.0106(9) 0.0030(8)
N1 0.0406(10) 0.0411(11) 0.0334(10) -0.0037(8) 0.0019(8) -0.0009(8)
C1 0.0290(10) 0.0393(12) 0.0329(11) 0.0014(9) -0.0010(9) -0.0041(9)
C2 0.0389(12) 0.0432(13) 0.0344(12) -0.0001(10) -0.0003(10) -0.0043(10)
C3 0.0346(11) 0.0455(13) 0.0339(11) -0.0059(9) 0.0018(9) -0.0081(9)
C4 0.0647(17) 0.0471(15) 0.0434(14) -0.0033(13) 0.0053(13) 0.0040(12)
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 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)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
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 C3 91.28(10) yes . .
C2 N1 C3 116.25(19) yes . .
C2 N1 C4 120.8(2) yes . .
C3 N1 C4 122.86(19) yes . .
S1 C1 C1 126.69(17) yes . 2_666
S1 C1 C2 111.33(15) yes . .
C1 C1 C2 121.99(19) yes 2_666 .
O1 C2 N1 125.3(2) yes . .
O1 C2 C1 125.2(2) yes . .
N1 C2 C1 109.41(19) yes . .
S1 C3 S2 122.40(14) yes . .
S1 C3 N1 111.71(15) yes . .
S2 C3 N1 125.88(17) 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 1.735(2) yes .
S1 C3 1.751(3) yes .
S2 C3 1.637(3) yes .
O1 C2 1.206(3) yes .
N1 C2 1.393(3) yes .
N1 C3 1.364(3) yes .
N1 C4 1.461(3) yes .
C1 C1 1.347(3) yes 2_666
C1 C2 1.476(3) yes .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 1575406
