#------------------------------------------------------------------------------
#$Date: 2025-08-22 23:12:46 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301866 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/68/7236875.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_7236875
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         'C12 H14 N2 O2 S4'
_chemical_formula_sum            'C12 H14 N2 O2 S4'
_chemical_formula_weight         346.49
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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
;
2017-06-27 deposited with the CCDC.
2017-08-16 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 102.4020
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   13.8023(2)
_cell_length_b                   8.15218(10)
_cell_length_c                   7.03233(10)
_cell_measurement_reflns_used    8317
_cell_measurement_temperature    296
_cell_measurement_theta_max      68.28
_cell_measurement_theta_min      3.28
_cell_volume                     772.805(18)
_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      296
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.1025
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8634
_diffrn_reflns_theta_full        68.23
_diffrn_reflns_theta_max         68.23
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.671
_exptl_absorpt_correction_T_max  0.868
_exptl_absorpt_correction_T_min  0.675
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             360.00
_exptl_crystal_size_max          0.227
_exptl_crystal_size_mid          0.202
_exptl_crystal_size_min          0.025
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.460
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1414
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0488
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0806P)²+0.1079P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1284
_reflns_number_gt                1306
_reflns_number_total             1414
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            c7tc02886e2.cif
_cod_data_source_block           O-N-Pr5
_cod_original_cell_volume        772.806(19)
_cod_database_code               7236875
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 0.45712(4) 0.39124(6) 0.20598(8) 0.0470(3) Uani 1.0 4 d .
S2 S 0.27133(5) 0.38945(8) -0.09623(9) 0.0664(3) Uani 1.0 4 d .
O1 O 0.34870(10) 0.6607(2) 0.5528(2) 0.0547(4) Uani 1.0 4 d .
N1 N 0.29857(10) 0.54267(18) 0.2503(3) 0.0404(4) Uani 1.0 4 d .
C1 C 0.46140(12) 0.4946(2) 0.4234(3) 0.0395(4) Uani 1.0 4 d .
C2 C 0.33263(14) 0.4471(3) 0.1176(3) 0.0445(5) Uani 1.0 4 d .
C3 C 0.36569(13) 0.5766(3) 0.4220(3) 0.0400(5) Uani 1.0 4 d .
C4 C 0.19906(14) 0.6152(3) 0.2144(4) 0.0457(5) Uani 1.0 4 d .
C5 C 0.12731(14) 0.5172(3) 0.3029(4) 0.0573(6) Uani 1.0 4 d .
C6 C 0.02669(17) 0.6001(4) 0.2670(4) 0.0677(7) Uani 1.0 4 d .
H4A H 0.1735 0.6235 0.0751 0.0549 Uiso 1.0 4 calc R
H4B H 0.2037 0.7254 0.2678 0.0549 Uiso 1.0 4 calc R
H5A H 0.1531 0.5062 0.4419 0.0688 Uiso 1.0 4 calc R
H5B H 0.1203 0.4081 0.2465 0.0688 Uiso 1.0 4 calc R
H6A H 0.0336 0.7082 0.3225 0.0813 Uiso 1.0 4 calc R
H6B H -0.0175 0.5369 0.3262 0.0813 Uiso 1.0 4 calc R
H6C H 0.0003 0.6078 0.1294 0.0813 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 C2 91.80(9) yes . .
C2 N1 C3 116.34(15) yes . .
C2 N1 C4 123.81(15) yes . .
C3 N1 C4 119.77(16) yes . .
S1 C1 C1 127.49(15) yes . 3_666
S1 C1 C3 110.63(12) yes . .
C1 C1 C3 121.88(17) yes 3_666 .
S1 C2 S2 121.76(13) yes . .
S1 C2 N1 110.99(13) yes . .
S2 C2 N1 127.25(14) yes . .
O1 C3 N1 125.04(17) yes . .
O1 C3 C1 124.75(16) yes . .
N1 C3 C1 110.21(16) yes . .
N1 C4 C5 112.93(16) yes . .
C4 C5 C6 110.77(19) yes . .
N1 C4 H4A 108.996 no . .
N1 C4 H4B 108.999 no . .
C5 C4 H4A 109.003 no . .
C5 C4 H4B 108.999 no . .
H4A C4 H4B 107.785 no . .
C4 C5 H5A 109.486 no . .
C4 C5 H5B 109.485 no . .
C6 C5 H5A 109.488 no . .
C6 C5 H5B 109.497 no . .
H5A C5 H5B 108.068 no . .
C5 C6 H6A 109.474 no . .
C5 C6 H6B 109.470 no . .
C5 C6 H6C 109.466 no . .
H6A C6 H6B 109.474 no . .
H6A C6 H6C 109.472 no . .
H6B C6 H6C 109.471 no . .
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 1.7354(19) yes .
S1 C2 1.7571(19) yes .
S2 C2 1.6284(19) yes .
O1 C3 1.210(3) yes .
N1 C2 1.373(3) yes .
N1 C3 1.383(3) yes .
N1 C4 1.467(3) yes .
C1 C1 1.346(3) yes 3_666
C1 C3 1.479(3) yes .
C4 C5 1.507(4) yes .
C5 C6 1.516(3) yes .
C4 H4A 0.970 no .
C4 H4B 0.970 no .
C5 H5A 0.970 no .
C5 H5B 0.970 no .
C6 H6A 0.960 no .
C6 H6B 0.960 no .
C6 H6C 0.960 no .
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_2
S1 O1 2.8788(14) no 3_666
S1 C3 3.1853(18) no 3_666
S2 C4 3.177(3) no .
O1 C1 2.883(3) no 3_666
O1 C2 3.486(3) no .
O1 C4 2.820(3) no .
O1 C5 3.389(3) no .
C2 C5 3.412(4) no .
C3 C5 3.252(3) no .
O1 N1 2.944(3) no 4_565
O1 C2 3.244(3) no 4_565
O1 C3 3.335(3) no 4_565
O1 C4 3.147(3) no 4_565
N1 O1 2.944(3) no 4_564
C2 O1 3.244(3) no 4_564
C3 O1 3.335(3) no 4_564
C4 O1 3.147(3) no 4_564
S2 H4A 2.7592 no .
S2 H5B 3.5117 no .
O1 H4B 2.5648 no .
O1 H5A 2.9290 no .
N1 H5A 2.6643 no .
N1 H5B 2.6883 no .
C2 H4A 2.5880 no .
C2 H4B 3.1993 no .
C2 H5B 3.2632 no .
C3 H4A 3.2178 no .
C3 H4B 2.5703 no .
C3 H5A 3.0225 no .
C4 H6A 2.6666 no .
C4 H6B 3.3126 no .
C4 H6C 2.6806 no .
C6 H4A 2.6719 no .
C6 H4B 2.6464 no .
H4A H5A 2.8214 no .
H4A H5B 2.3355 no .
H4A H6A 2.9454 no .
H4A H6B 3.5459 no .
H4A H6C 2.5046 no .
H4B H5A 2.3548 no .
H4B H5B 2.8212 no .
H4B H6A 2.4624 no .
H4B H6B 3.5201 no .
H4B H6C 2.9281 no .
H5A H6A 2.3534 no .
H5A H6B 2.3340 no .
H5A H6C 2.8239 no .
H5B H6A 2.8241 no .
H5B H6B 2.3444 no .
H5B H6C 2.3430 no .
S2 H4B 3.3561 no 4_564
S2 H5A 3.4413 no 1_554
S2 H5B 3.2344 no 4_554
S2 H6B 3.5796 no 3_565
O1 H4A 3.0213 no 4_565
O1 H4B 2.9079 no 4_565
C4 H4A 3.3879 no 4_565
C4 H4B 3.4126 no 4_564
C4 H6A 3.4898 no 4_564
C5 H4A 3.4821 no 4_565
C5 H6A 3.3494 no 2_545
C5 H6B 3.3152 no 3_566
C5 H6C 3.3287 no 3_565
C6 H4A 3.4629 no 4_565
C6 H5B 3.2170 no 2_555
C6 H6A 3.3278 no 2_545
C6 H6A 3.5140 no 4_564
C6 H6B 3.0988 no 3_566
C6 H6C 3.2149 no 3_565
C6 H6C 3.5631 no 4_565
H4A O1 3.0213 no 4_564
H4A C4 3.3879 no 4_564
H4A C5 3.4821 no 4_564
H4A C6 3.4629 no 4_564
H4A H4B 2.5976 no 4_564
H4A H5A 3.1550 no 4_564
H4A H6A 2.7003 no 4_564
H4A H6B 3.4203 no 3_565
H4A H6C 3.1458 no 3_565
H4B S2 3.3561 no 4_565
H4B O1 2.9079 no 4_564
H4B C4 3.4126 no 4_565
H4B H4A 2.5976 no 4_565
H4B H4B 3.5390 no 4_564
H4B H4B 3.5390 no 4_565
H4B H5A 3.1369 no 4_564
H4B H6A 3.5282 no 4_564
H4B H6B 3.5716 no 2_555
H5A S2 3.4413 no 1_556
H5A H4A 3.1550 no 4_565
H5A H4B 3.1369 no 4_565
H5A H6B 2.7556 no 3_566
H5B S2 3.2344 no 4_555
H5B C6 3.2170 no 2_545
H5B H6A 2.6394 no 2_545
H5B H6B 3.3351 no 2_545
H5B H6C 3.1859 no 2_545
H5B H6C 2.8078 no 3_565
H6A C4 3.4898 no 4_565
H6A C5 3.3494 no 2_555
H6A C6 3.3278 no 2_555
H6A C6 3.5140 no 4_565
H6A H4A 2.7003 no 4_565
H6A H4B 3.5282 no 4_565
H6A H5B 2.6394 no 2_555
H6A H6A 3.5817 no 4_564
H6A H6A 3.5817 no 4_565
H6A H6B 2.8678 no 2_555
H6A H6B 3.2213 no 3_566
H6A H6C 3.3192 no 2_555
H6A H6C 2.7468 no 4_565
H6B S2 3.5796 no 3_565
H6B C5 3.3152 no 3_566
H6B C6 3.0988 no 3_566
H6B H4A 3.4203 no 3_565
H6B H4B 3.5716 no 2_545
H6B H5A 2.7556 no 3_566
H6B H5B 3.3351 no 2_555
H6B H6A 2.8678 no 2_545
H6B H6A 3.2213 no 3_566
H6B H6B 2.4619 no 3_566
H6B H6C 3.5150 no 2_545
H6B H6C 3.4702 no 3_565
H6B H6C 3.5734 no 4_565
H6C C5 3.3287 no 3_565
H6C C6 3.2149 no 3_565
H6C C6 3.5631 no 4_564
H6C H4A 3.1458 no 3_565
H6C H5B 3.1859 no 2_555
H6C H5B 2.8078 no 3_565
H6C H6A 3.3192 no 2_545
H6C H6A 2.7468 no 4_564
H6C H6B 3.5150 no 2_555
H6C H6B 3.4702 no 3_565
H6C H6B 3.5734 no 4_564
H6C H6C 2.5292 no 3_565
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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C1 S1 C2 S2 -179.57(14) no . . .
C1 S1 C2 N1 0.98(14) no . . .
C2 S1 C1 C1 178.97(16) no . . 3_666
C2 S1 C1 C3 -1.78(12) no . . .
C2 N1 C3 O1 178.71(17) no . . .
C2 N1 C3 C1 -1.5(3) no . . .
C3 N1 C2 S1 0.2(2) no . . .
C3 N1 C2 S2 -179.25(15) no . . .
C2 N1 C4 C5 98.6(2) no . . .
C4 N1 C2 S1 176.83(14) no . . .
C4 N1 C2 S2 -2.6(3) no . . .
C3 N1 C4 C5 -84.87(19) no . . .
C4 N1 C3 O1 1.9(3) no . . .
C4 N1 C3 C1 -178.31(14) no . . .
S1 C1 C1 S1 180.00(11) no . 3_666 3_666
S1 C1 C1 C3 -0.8(3) no . 3_666 3_666
S1 C1 C3 O1 -178.04(14) no . . .
S1 C1 C3 N1 2.17(18) no . . .
C1 C1 C3 O1 1.3(3) no 3_666 . .
C1 C1 C3 N1 -178.53(16) no 3_666 . .
C3 C1 C1 S1 0.8(3) no . 3_666 3_666
C3 C1 C1 C3 180.00(18) no . 3_666 3_666
N1 C4 C5 C6 178.25(15) no . . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139230856
