#------------------------------------------------------------------------------
#$Date: 2020-10-08 04:46:38 +0300 (Thu, 08 Oct 2020) $
#$Revision: 258246 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/13/7241378.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_7241378
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         'C10 H10 N2 O2 S4'
_chemical_formula_sum            'C10 H10 N2 O2 S4'
_chemical_formula_weight         318.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 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                90.0000
_cell_angle_beta                 106.595(3)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   14.3245(9)
_cell_length_b                   4.9698(3)
_cell_length_c                   19.9041(12)
_cell_measurement_reflns_used    5457
_cell_measurement_temperature    274
_cell_measurement_theta_max      68.15
_cell_measurement_theta_min      3.22
_cell_volume                     1357.95(15)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.3'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_structure_refinement  'SHELXL Version 2018/3 (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 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  0.1548
_diffrn_reflns_av_unetI/netI     0.1834
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13966
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.596
_diffrn_reflns_theta_max         66.596
_diffrn_reflns_theta_min         3.219
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.401
_exptl_absorpt_correction_T_max  0.938
_exptl_absorpt_correction_T_min  0.499
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             656.00
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.48
_refine_diff_density_min         -0.48
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.876
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2393
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.1507
_refine_ls_R_factor_gt           0.0740
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0947P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1579
_refine_ls_wR_factor_ref         0.2123
_reflns_Friedel_coverage         0.000
_reflns_number_gt                968
_reflns_number_total             2393
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            d0ce01133a2.cif
_cod_data_source_block           20190906
_cod_original_cell_volume        1357.94(14)
_cod_database_code               7241378
loop_
_space_group_symop_id
_space_group_symop_operation_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_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 0.49357(12) 0.7426(3) 0.42559(8) 0.0756(6) Uani 1 1 d . . . . .
S2 S 0.67930(12) 0.3769(3) 0.45264(8) 0.0727(6) Uani 1 1 d . . . . .
S3 S 0.31791(15) 1.0873(4) 0.39930(10) 0.0985(7) Uani 1 1 d . . . . .
S4 S 0.84918(14) 0.0125(3) 0.47326(10) 0.0901(7) Uani 1 1 d . . . . .
O1 O 0.5714(3) 1.0611(7) 0.2744(2) 0.0746(13) Uani 1 1 d . . . . .
O2 O 0.7252(3) 0.7125(9) 0.2910(2) 0.0857(15) Uani 1 1 d . . . . .
N1 N 0.4505(4) 1.0899(8) 0.3279(3) 0.0698(15) Uani 1 1 d . . . . .
H1 H 0.420889 1.218462 0.301287 0.084 Uiso 1 1 calc R U . . .
N2 N 0.7901(4) 0.3818(9) 0.3715(3) 0.0713(15) Uani 1 1 d . . . . .
C1 C 0.4137(5) 0.9905(11) 0.3800(3) 0.0691(18) Uani 1 1 d . . . . .
C2 C 0.5343(5) 0.9832(11) 0.3186(3) 0.0639(17) Uani 1 1 d . . . . .
C3 C 0.5721(4) 0.7674(10) 0.3726(3) 0.0643(17) Uani 1 1 d . . . . .
C4 C 0.6508(5) 0.6065(10) 0.3834(3) 0.0658(18) Uani 1 1 d . . . . .
C5 C 0.7220(5) 0.5852(12) 0.3409(4) 0.0730(19) Uani 1 1 d . . . . .
C6 C 0.7796(4) 0.2519(11) 0.4299(3) 0.0697(17) Uani 1 1 d . . . . .
C7 C 0.8657(5) 0.3157(13) 0.3376(4) 0.094(2) Uani 1 1 d . . . . .
H7A H 0.842000 0.357420 0.288027 0.113 Uiso 1 1 calc R U . . .
H7B H 0.879288 0.124333 0.342224 0.113 Uiso 1 1 calc R U . . .
C8 C 0.9596(6) 0.4721(13) 0.3699(4) 0.113(3) Uani 1 1 d . . . . .
H8A H 0.946621 0.663594 0.364448 0.136 Uiso 1 1 calc R U . . .
H8B H 0.982983 0.433092 0.419694 0.136 Uiso 1 1 calc R U . . .
C9 C 1.0364(6) 0.3973(15) 0.3354(5) 0.138(3) Uani 1 1 d . . . . .
H9A H 1.056160 0.212758 0.347691 0.166 Uiso 1 1 calc R U . . .
H9B H 1.007925 0.404302 0.284996 0.166 Uiso 1 1 calc R U . . .
C10 C 1.1204(6) 0.5618(15) 0.3534(5) 0.148(3) Uani 1 1 d . . . . .
H10A H 1.152579 0.544820 0.402625 0.221 Uiso 1 1 calc R U . . .
H10B H 1.101821 0.745959 0.342638 0.221 Uiso 1 1 calc R U . . .
H10C H 1.163850 0.506466 0.327152 0.221 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 C3 94.3(3) . . ?
C6 S2 C4 93.0(3) . . ?
C2 N1 C1 119.9(5) . . ?
C2 N1 H1 120.0 . . ?
C1 N1 H1 120.0 . . ?
C6 N2 C5 118.0(6) . . ?
C6 N2 C7 123.9(5) . . ?
C5 N2 C7 118.1(6) . . ?
N1 C1 S3 127.6(5) . . ?
N1 C1 S1 108.0(4) . . ?
S3 C1 S1 124.4(4) . . ?
O1 C2 N1 123.7(6) . . ?
O1 C2 C3 127.1(6) . . ?
N1 C2 C3 109.2(6) . . ?
C4 C3 C2 130.5(6) . . ?
C4 C3 S1 121.0(5) . . ?
C2 C3 S1 108.6(5) . . ?
C3 C4 C5 128.6(6) . . ?
C3 C4 S2 120.6(5) . . ?
C5 C4 S2 110.8(5) . . ?
O2 C5 N2 123.5(7) . . ?
O2 C5 C4 128.8(6) . . ?
N2 C5 C4 107.7(6) . . ?
N2 C6 S4 126.2(5) . . ?
N2 C6 S2 110.5(4) . . ?
S4 C6 S2 123.2(4) . . ?
N2 C7 C8 111.7(6) . . ?
N2 C7 H7A 109.3 . . ?
C8 C7 H7A 109.3 . . ?
N2 C7 H7B 109.3 . . ?
C8 C7 H7B 109.3 . . ?
H7A C7 H7B 107.9 . . ?
C9 C8 C7 110.7(7) . . ?
C9 C8 H8A 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
C10 C9 C8 115.0(8) . . ?
C10 C9 H9A 108.5 . . ?
C8 C9 H9A 108.5 . . ?
C10 C9 H9B 108.5 . . ?
C8 C9 H9B 108.5 . . ?
H9A C9 H9B 107.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
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 1.749(6) . ?
S1 C3 1.752(6) . ?
S2 C6 1.739(6) . ?
S2 C4 1.746(6) . ?
S3 C1 1.601(7) . ?
S4 C6 1.632(6) . ?
O1 C2 1.214(6) . ?
O2 C5 1.190(7) . ?
N1 C2 1.373(7) . ?
N1 C1 1.382(6) . ?
N1 H1 0.8600 . ?
N2 C6 1.375(6) . ?
N2 C5 1.417(7) . ?
N2 C7 1.467(7) . ?
C2 C3 1.506(7) . ?
C3 C4 1.349(8) . ?
C4 C5 1.501(8) . ?
C7 C8 1.528(9) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.501(9) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.413(10) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 O1 . . 2_655 3.059(6) 0.860 2.297 147.8 no
N1 H1 O2 . . 2_655 2.983(6) 0.860 2.358 129.9 no
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 N1 C1 S3 179.8(5) . . . . ?
C2 N1 C1 S1 2.2(7) . . . . ?
C3 S1 C1 N1 -1.9(4) . . . . ?
C3 S1 C1 S3 -179.6(4) . . . . ?
C1 N1 C2 O1 -179.4(5) . . . . ?
C1 N1 C2 C3 -1.3(7) . . . . ?
O1 C2 C3 C4 -2.8(10) . . . . ?
N1 C2 C3 C4 179.1(6) . . . . ?
O1 C2 C3 S1 177.7(5) . . . . ?
N1 C2 C3 S1 -0.3(6) . . . . ?
C1 S1 C3 C4 -178.2(5) . . . . ?
C1 S1 C3 C2 1.3(4) . . . . ?
C2 C3 C4 C5 -3.9(10) . . . . ?
S1 C3 C4 C5 175.5(4) . . . . ?
C2 C3 C4 S2 178.2(4) . . . . ?
S1 C3 C4 S2 -2.4(7) . . . . ?
C6 S2 C4 C3 178.2(5) . . . . ?
C6 S2 C4 C5 0.0(4) . . . . ?
C6 N2 C5 O2 178.9(6) . . . . ?
C7 N2 C5 O2 -3.2(9) . . . . ?
C6 N2 C5 C4 -0.1(7) . . . . ?
C7 N2 C5 C4 177.8(5) . . . . ?
C3 C4 C5 O2 3.0(11) . . . . ?
S2 C4 C5 O2 -178.9(6) . . . . ?
C3 C4 C5 N2 -178.0(5) . . . . ?
S2 C4 C5 N2 0.1(6) . . . . ?
C5 N2 C6 S4 179.9(4) . . . . ?
C7 N2 C6 S4 2.1(9) . . . . ?
C5 N2 C6 S2 0.1(6) . . . . ?
C7 N2 C6 S2 -177.6(5) . . . . ?
C4 S2 C6 N2 -0.1(4) . . . . ?
C4 S2 C6 S4 -179.8(4) . . . . ?
C6 N2 C7 C8 -88.0(7) . . . . ?
C5 N2 C7 C8 94.2(7) . . . . ?
N2 C7 C8 C9 178.9(6) . . . . ?
C7 C8 C9 C10 170.0(8) . . . . ?
