#------------------------------------------------------------------------------
#$Date: 2025-08-19 21:30:04 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301811 $
#$URL: svn://www.crystallography.net/cod/cif/4/00/29/4002970.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_4002970
loop_
_publ_author_name
'Takenaka, Hiroyuki'
'Ogaki, Takuya'
'Wang, Chengyuan'
'Kawabata, Kohsuke'
'Takimiya, Kazuo'
_publ_section_title
;
 Selenium-Substituted β-Methylthiobenzo[1,2-b:4,5-b′]dithiophenes:
 Synthesis, Packing Structure, and Transport Properties
;
_journal_issue                   17
_journal_name_full               'Chemistry of Materials'
_journal_page_first              6696
_journal_paper_doi               10.1021/acs.chemmater.9b01187
_journal_volume                  31
_journal_year                    2019
_chemical_formula_moiety         'C12 H10 S2 Se2'
_chemical_formula_sum            'C12 H10 S2 Se2'
_chemical_formula_weight         376.25
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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
_cell_angle_alpha                81.0598(15)
_cell_angle_beta                 80.9249(15)
_cell_angle_gamma                71.7042(13)
_cell_formula_units_Z            1
_cell_length_a                   5.32021(10)
_cell_length_b                   7.28902(17)
_cell_length_c                   8.31911(19)
_cell_measurement_reflns_used    2440
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.08
_cell_measurement_theta_min      5.42
_cell_volume                     300.530(12)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.2.5'
_computing_publication_material  'CrystalStructure 4.2.5 (Rigaku, 2017)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_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  0.1528
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5361
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.208
_diffrn_reflns_theta_min         5.420
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    10.647
_exptl_absorpt_correction_T_max  0.727
_exptl_absorpt_correction_T_min  0.068
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.079
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             182.00
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.410
_exptl_crystal_size_min          0.030
_refine_diff_density_max         1.70
_refine_diff_density_min         -1.15
_refine_ls_extinction_coef       0.018(2)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     74
_refine_ls_number_reflns         1085
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0566
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0619P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1393
_refine_ls_wR_factor_ref         0.1442
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1012
_reflns_number_total             1085
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            cm9b01187_si_002.cif
_cod_data_source_block           BDT-SeMe_plate
_cod_database_code               4002970
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
Se1 Se 0.18376(8) 0.17066(7) 0.72142(5) 0.0174(3) Uani 1 1 d . .
S1 S -0.2118(2) 0.7904(2) 0.80483(14) 0.0166(4) Uani 1 1 d . .
C1 C -0.3771(9) 0.2992(8) 0.9749(5) 0.0180(11) Uani 1 1 d . .
H1 H -0.2973 0.1664 0.9582 0.022 Uiso 1 1 calc R U
C2 C -0.3905(9) 0.6415(7) 0.9181(5) 0.0153(11) Uani 1 1 d . .
C3 C -0.2662(9) 0.4438(7) 0.8929(5) 0.0129(10) Uani 1 1 d . .
C4 C -0.0259(10) 0.4211(7) 0.7779(6) 0.0149(10) Uani 1 1 d . .
C5 C 0.0233(9) 0.5924(8) 0.7230(6) 0.0164(11) Uani 1 1 d . .
H5 H 0.1725 0.6034 0.6469 0.020 Uiso 1 1 calc R U
C6 C 0.4614(9) 0.2519(8) 0.5734(6) 0.0205(12) Uani 1 1 d . .
H6A H 0.5933 0.1378 0.5302 0.025 Uiso 1 1 calc R U
H6B H 0.3817 0.3430 0.4826 0.025 Uiso 1 1 calc R U
H6C H 0.5489 0.3159 0.6331 0.025 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)
;
S S 0.3331 0.5567
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Se Se -0.7943 1.1372
;
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
C4 Se1 C6 97.5(2) .
C5 S1 C2 91.3(2) .
C2 C1 C3 117.3(5) 2_467
C2 C1 H1 121.4 2_467
C3 C1 H1 121.4 .
C1 C2 C3 122.3(5) 2_467
C1 C2 S1 126.3(4) 2_467
C3 C2 S1 111.3(4) .
C1 C3 C2 120.4(4) .
C1 C3 C4 128.3(4) .
C2 C3 C4 111.3(4) .
C5 C4 C3 112.4(5) .
C5 C4 Se1 127.0(4) .
C3 C4 Se1 120.6(4) .
C4 C5 S1 113.6(4) .
C4 C5 H5 123.2 .
S1 C5 H5 123.2 .
Se1 C6 H6A 109.5 .
Se1 C6 H6B 109.5 .
H6A C6 H6B 109.5 .
Se1 C6 H6C 109.5 .
H6A C6 H6C 109.5 .
H6B C6 H6C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Se1 C4 1.903(5) .
Se1 C6 1.949(5) .
S1 C5 1.736(5) .
S1 C2 1.737(5) .
C1 C2 1.394(6) 2_467
C1 C3 1.401(7) .
C1 H1 0.9500 .
C2 C1 1.394(6) 2_467
C2 C3 1.418(7) .
C3 C4 1.452(6) .
C4 C5 1.351(8) .
C5 H5 0.9500 .
C6 H6A 0.9800 .
C6 H6B 0.9800 .
C6 H6C 0.9800 .
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_4
C5 S1 C2 C1 179.0(4) . 2_467
C5 S1 C2 C3 0.7(3) . .
C2 C1 C3 C2 -0.8(7) 2_467 .
C2 C1 C3 C4 179.1(4) 2_467 .
C1 C2 C3 C1 0.8(7) 2_467 .
S1 C2 C3 C1 179.2(3) . .
C1 C2 C3 C4 -179.1(4) 2_467 .
S1 C2 C3 C4 -0.7(5) . .
C1 C3 C4 C5 -179.5(5) . .
C2 C3 C4 C5 0.4(6) . .
C1 C3 C4 Se1 -0.2(6) . .
C2 C3 C4 Se1 179.7(3) . .
C3 C4 C5 S1 0.1(6) . .
Se1 C4 C5 S1 -179.1(2) . .
C2 S1 C5 C4 -0.5(4) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168327424
