#------------------------------------------------------------------------------
#$Date: 2025-08-19 21:30:04 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301811 $
#$URL: svn://www.crystallography.net/cod/cif/4/00/29/4002969.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_4002969
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      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   14.5203(4)
_cell_length_b                   5.27442(15)
_cell_length_c                   15.8554(4)
_cell_measurement_reflns_used    12403
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.25
_cell_measurement_theta_min      3.04
_cell_volume                     1214.30(6)
_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 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  0.1495
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17338
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.254
_diffrn_reflns_theta_min         5.581
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    10.540
_exptl_absorpt_correction_T_max  0.729
_exptl_absorpt_correction_T_min  0.456
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.058
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             728.00
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.94
_refine_diff_density_min         -1.92
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     74
_refine_ls_number_reflns         1113
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0586
_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          0.1527
_refine_ls_wR_factor_ref         0.1605
_reflns_Friedel_coverage         0.000
_reflns_number_gt                855
_reflns_number_total             1113
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            cm9b01187_si_003.cif
_cod_data_source_block           beta-MT-BDS
_cod_database_code               4002969
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2+X,1/2-Y,-Z
3 -X,1/2+Y,1/2-Z
4 1/2-X,-Y,1/2+Z
5 -X,-Y,-Z
6 -1/2-X,-1/2+Y,+Z
7 +X,-1/2-Y,-1/2+Z
8 -1/2+X,+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
Se1 Se 0.65556(5) 0.87370(14) 0.41928(4) 0.0374(4) Uani 1 1 d . .
S1 S 0.58867(11) 0.9475(3) 0.69178(10) 0.0405(5) Uani 1 1 d . .
C1 C 0.6618(4) 0.9993(15) 0.5299(4) 0.0406(16) Uani 1 1 d . .
H1 H 0.7019 1.1328 0.5463 0.049 Uiso 1 1 calc R U
C2 C 0.6038(5) 0.8817(12) 0.5841(4) 0.0355(16) Uani 1 1 d . .
C3 C 0.5480(4) 0.6824(13) 0.5469(4) 0.0357(15) Uani 1 1 d . .
C4 C 0.5638(4) 0.6469(12) 0.4593(4) 0.0356(15) Uani 1 1 d . .
C5 C 0.5171(5) 0.4662(14) 0.4132(3) 0.0361(15) Uani 1 1 d . .
H5 H 0.5295 0.4444 0.3548 0.043 Uiso 1 1 calc R U
C6 C 0.6641(4) 1.2167(15) 0.7066(5) 0.0440(17) Uani 1 1 d . .
H6A H 0.6633 1.2676 0.7661 0.053 Uiso 1 1 calc R U
H6B H 0.6428 1.3582 0.6716 0.053 Uiso 1 1 calc R U
H6C H 0.7269 1.1703 0.6903 0.053 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
_geom_angle_site_symmetry_3
C1 Se1 C4 86.8(3) . .
C2 S1 C6 101.9(3) . .
C2 C1 Se1 113.7(5) . .
C2 C1 H1 123.2 . .
Se1 C1 H1 123.2 . .
C1 C2 C3 114.9(6) . .
C1 C2 S1 127.2(5) . .
C3 C2 S1 117.9(5) . .
C5 C3 C4 118.9(6) 5_666 .
C5 C3 C2 127.4(6) 5_666 .
C4 C3 C2 113.7(6) . .
C5 C4 C3 122.0(6) . .
C5 C4 Se1 127.1(5) . .
C3 C4 Se1 110.9(5) . .
C4 C5 C3 119.1(6) . 5_666
C4 C5 H5 120.5 . .
C3 C5 H5 120.5 5_666 .
S1 C6 H6A 109.5 . .
S1 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
S1 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 C1 1.877(7) .
Se1 C4 1.900(6) .
S1 C2 1.756(6) .
S1 C6 1.809(7) .
C1 C2 1.354(9) .
C1 H1 0.9500 .
C2 C3 1.453(9) .
C3 C5 1.381(9) 5_666
C3 C4 1.420(9) .
C4 C5 1.379(9) .
C5 C3 1.381(9) 5_666
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
C4 Se1 C1 C2 0.4(5) . .
Se1 C1 C2 C3 -0.1(8) . .
Se1 C1 C2 S1 -179.2(4) . .
C6 S1 C2 C1 3.2(7) . .
C6 S1 C2 C3 -175.9(5) . .
C1 C2 C3 C5 -179.4(7) . 5_666
S1 C2 C3 C5 -0.2(9) . 5_666
C1 C2 C3 C4 -0.4(8) . .
S1 C2 C3 C4 178.8(5) . .
C5 C3 C4 C5 -0.9(11) 5_666 .
C2 C3 C4 C5 -180.0(6) . .
C5 C3 C4 Se1 179.7(5) 5_666 .
C2 C3 C4 Se1 0.7(7) . .
C1 Se1 C4 C5 -179.9(6) . .
C1 Se1 C4 C3 -0.6(5) . .
C3 C4 C5 C3 0.9(11) . 5_666
Se1 C4 C5 C3 -179.8(5) . 5_666
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168327423
