#------------------------------------------------------------------------------
#$Date: 2020-10-08 04:46:38 +0300 (Thu, 08 Oct 2020) $
#$Revision: 258246 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/13/7241376.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_7241376
loop_
_publ_author_name
'Sumimoto, Yuji'
'Iijima, Kodai'
'Yoo, Dongho'
'Kawamoto, Tadashi'
'Le Gal, Yann'
'Lorcy, Dominique'
'Mori, Takehiko'
_publ_section_title
;
 Structures and transistor properties of extended and unsymmetrical
 birhodanines
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE01133A
_journal_year                    2020
_chemical_formula_moiety         'C18 H10 N2 O2 S4'
_chemical_formula_sum            'C18 H10 N2 O2 S4'
_chemical_formula_weight         414.53
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2020-07-20 deposited with the CCDC.	2020-09-10 downloaded from the CCDC.
;
_cell_angle_alpha                108.240(3)
_cell_angle_beta                 98.143(4)
_cell_angle_gamma                96.693(4)
_cell_formula_units_Z            1
_cell_length_a                   4.8107(4)
_cell_length_b                   9.0732(6)
_cell_length_c                   11.0382(6)
_cell_measurement_reflns_used    463
_cell_measurement_temperature    274
_cell_measurement_theta_max      67.19
_cell_measurement_theta_min      8.45
_cell_volume                     446.30(5)
_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      274
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.984
_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  0.1151
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4892
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.208
_diffrn_reflns_theta_min         4.295
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.030
_exptl_absorpt_correction_T_max  0.904
_exptl_absorpt_correction_T_min  0.258
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             212.00
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.57
_refine_diff_density_min         -0.55
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1611
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1228
_refine_ls_R_factor_gt           0.0796
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0912P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1775
_refine_ls_wR_factor_ref         0.2371
_reflns_Friedel_coverage         0.000
_reflns_number_gt                805
_reflns_number_total             1611
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            d0ce01133a2.cif
_cod_data_source_block           20190111
_cod_database_code               7241376
loop_
_space_group_symop_id
_space_group_symop_operation_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_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 0.2252(4) 0.36041(17) 0.35498(13) 0.0566(6) Uani 1 1 d . . . . .
S2 S 0.5145(4) 0.42599(19) 0.15354(14) 0.0678(7) Uani 1 1 d . . . . .
O1 O 0.0062(10) 0.7668(5) 0.4693(4) 0.0614(13) Uani 1 1 d . . . . .
N1 N 0.2485(11) 0.6264(5) 0.3117(4) 0.0499(14) Uani 1 1 d . . . . .
C1 C 0.0697(14) 0.5045(7) 0.4510(5) 0.0518(17) Uani 1 1 d . . . . .
C2 C 0.3314(14) 0.4841(7) 0.2692(5) 0.0555(19) Uani 1 1 d . . . . .
C3 C 0.1020(13) 0.6498(7) 0.4148(5) 0.0478(15) Uani 1 1 d . . . . .
C4 C 0.2889(15) 0.7503(7) 0.2555(5) 0.0529(17) Uani 1 1 d . . . . .
C5 C 0.4979(17) 0.8761(8) 0.3136(6) 0.072(2) Uani 1 1 d . . . . .
H5 H 0.614707 0.885344 0.391235 0.086 Uiso 1 1 calc R U . . .
C6 C 0.5379(16) 0.9914(7) 0.2571(6) 0.069(2) Uani 1 1 d . . . . .
H6 H 0.682343 1.078216 0.296369 0.083 Uiso 1 1 calc R U . . .
C7 C 0.3654(17) 0.9771(8) 0.1440(7) 0.070(2) Uani 1 1 d . . . . .
H7 H 0.390443 1.055012 0.106372 0.084 Uiso 1 1 calc R U . . .
C8 C 0.1537(17) 0.8477(8) 0.0847(6) 0.071(2) Uani 1 1 d . . . . .
H8 H 0.036433 0.838625 0.007227 0.085 Uiso 1 1 calc R U . . .
C9 C 0.1151(16) 0.7327(7) 0.1393(6) 0.073(2) Uani 1 1 d . . . . .
H9 H -0.025523 0.644203 0.098966 0.087 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
_geom_angle_publ_flag
C1 S1 C2 91.1(3) . . ?
C2 N1 C3 115.8(5) . . ?
C2 N1 C4 125.5(5) . . ?
C3 N1 C4 118.6(5) . . ?
C1 C1 C3 121.2(7) 2_566 . ?
C1 C1 S1 127.4(6) 2_566 . ?
C3 C1 S1 111.3(4) . . ?
N1 C2 S2 126.6(5) . . ?
N1 C2 S1 112.4(5) . . ?
S2 C2 S1 121.0(3) . . ?
O1 C3 N1 128.0(6) . . ?
O1 C3 C1 122.7(5) . . ?
N1 C3 C1 109.3(5) . . ?
C5 C4 C9 121.3(6) . . ?
C5 C4 N1 120.4(5) . . ?
C9 C4 N1 118.3(5) . . ?
C4 C5 C6 119.6(6) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C7 C6 C5 119.7(6) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C8 120.3(6) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C9 C8 C7 120.3(6) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C4 118.7(6) . . ?
C8 C9 H9 120.6 . . ?
C4 C9 H9 120.6 . . ?
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 C1 1.726(6) . ?
S1 C2 1.757(6) . ?
S2 C2 1.640(7) . ?
O1 C3 1.223(7) . ?
N1 C2 1.357(6) . ?
N1 C3 1.395(7) . ?
N1 C4 1.452(7) . ?
C1 C1 1.370(12) 2_566 ?
C1 C3 1.490(8) . ?
C4 C5 1.348(8) . ?
C4 C9 1.380(7) . ?
C5 C6 1.384(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.358(8) . ?
C6 H6 0.9300 . ?
C7 C8 1.376(9) . ?
C7 H7 0.9300 . ?
C8 C9 1.367(8) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
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
C2 S1 C1 C1 179.9(8) . . . 2_566 ?
C2 S1 C1 C3 0.0(4) . . . . ?
C3 N1 C2 S2 -177.9(4) . . . . ?
C4 N1 C2 S2 5.0(9) . . . . ?
C3 N1 C2 S1 1.1(7) . . . . ?
C4 N1 C2 S1 -176.1(4) . . . . ?
C1 S1 C2 N1 -0.6(5) . . . . ?
C1 S1 C2 S2 178.4(4) . . . . ?
C2 N1 C3 O1 -179.8(6) . . . . ?
C4 N1 C3 O1 -2.5(9) . . . . ?
C2 N1 C3 C1 -1.0(7) . . . . ?
C4 N1 C3 C1 176.3(5) . . . . ?
C1 C1 C3 O1 -0.4(10) 2_566 . . . ?
S1 C1 C3 O1 179.4(5) . . . . ?
C1 C1 C3 N1 -179.3(7) 2_566 . . . ?
S1 C1 C3 N1 0.5(6) . . . . ?
C2 N1 C4 C5 -102.6(8) . . . . ?
C3 N1 C4 C5 80.3(8) . . . . ?
C2 N1 C4 C9 75.0(9) . . . . ?
C3 N1 C4 C9 -102.0(7) . . . . ?
C9 C4 C5 C6 0.9(11) . . . . ?
N1 C4 C5 C6 178.5(6) . . . . ?
C4 C5 C6 C7 0.3(11) . . . . ?
C5 C6 C7 C8 -0.8(11) . . . . ?
C6 C7 C8 C9 0.1(11) . . . . ?
C7 C8 C9 C4 1.1(11) . . . . ?
C5 C4 C9 C8 -1.6(11) . . . . ?
N1 C4 C9 C8 -179.2(6) . . . . ?
