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#$Date: 2025-08-19 22:30:04 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301811 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/00/32/4003278.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_4003278
loop_
_publ_author_name
'Takai, Atsuro'
'Chen, Zhihua'
'Yu, Xinge'
'Zhou, Nanjia'
'Marks, Tobin J.'
'Facchetti, Antonio'
_publ_section_title
;
 Annulated Thienyl-Vinylene-Thienyl Building Blocks for π-Conjugated
 Copolymers: Ring Dimensions and Isomeric Structure Effects on
 π-Conjugation Length and Charge Transport
;
_journal_issue                   16
_journal_name_full               'Chemistry of Materials'
_journal_page_first              5772
_journal_paper_doi               10.1021/acs.chemmater.6b02007
_journal_volume                  28
_journal_year                    2016
_chemical_formula_moiety         'C14 H12 S2'
_chemical_formula_sum            'C14 H12 S2'
_chemical_formula_weight         244.36
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_Hall           '-P 2ab 2ac'
_space_group_name_H-M_alt        'P c c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2014-01-10
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.9002(18)
_cell_length_b                   8.6559(7)
_cell_length_c                   6.2386(6)
_cell_measurement_reflns_used    3109
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.016
_cell_measurement_theta_min      4.231
_cell_volume                     1128.63(17)
_computing_cell_refinement       'SAINT V7.23A (Bruker, 2005)'
_computing_data_collection       'APEX2 V2.1-4 (Bruker, 2007)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXD (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'MX optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0671
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            6465
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.001
_diffrn_reflns_theta_min         4.230
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    3.972
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.5249
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1270 before and 0.0752 after correction.
The Ratio of minimum to maximum transmission is 0.6971.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_description       plate
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.228
_exptl_crystal_size_mid          0.119
_exptl_crystal_size_min          0.032
_refine_diff_density_max         0.700
_refine_diff_density_min         -0.474
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     73
_refine_ls_number_reflns         1014
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.147
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0630
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1030P)²+1.7798P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1865
_refine_ls_wR_factor_ref         0.1945
_reflns_Friedel_coverage         0.000
_reflns_number_gt                821
_reflns_number_total             1014
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cm6b02007_si_002.cif
_cod_data_source_block           n3260
_cod_database_code               4003278
_shelxl_version_number           2013-4
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.883
_shelx_estimated_absorpt_t_min   0.465
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C004(H00A,H00B), C008(H00C,H00D)
2.b Aromatic/amide H refined with riding coordinates:
 C006(H006), C007(H007)
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'
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
S001 S 0.79739(5) 0.47416(12) 0.22860(17) 0.0368(5) Uani 1 1 d .
C002 C 0.9688(2) 0.5180(4) -0.0070(6) 0.0340(9) Uani 1 1 d .
C003 C 0.91716(19) 0.4680(4) 0.1351(7) 0.0335(10) Uani 1 1 d .
C004 C 0.86577(19) 0.6312(5) -0.1252(7) 0.0405(10) Uani 1 1 d .
H00A H 0.8525 0.7384 -0.0925 0.049 Uiso 1 1 calc R
H00B H 0.8398 0.5913 -0.2458 0.049 Uiso 1 1 calc R
C005 C 0.86018(19) 0.5294(4) 0.0679(7) 0.0349(10) Uani 1 1 d .
C006 C 0.9102(2) 0.3735(5) 0.3225(6) 0.0379(10) Uani 1 1 d .
H006 H 0.9446 0.3218 0.3915 0.045 Uiso 1 1 calc R
C007 C 0.8485(2) 0.3674(5) 0.3889(7) 0.0383(10) Uani 1 1 d .
H007 H 0.8347 0.3104 0.5106 0.046 Uiso 1 1 calc R
C008 C 0.9381(2) 0.6222(5) -0.1757(6) 0.0372(10) Uani 1 1 d .
H00C H 0.9449 0.5788 -0.3208 0.045 Uiso 1 1 calc R
H00D H 0.9574 0.7266 -0.1706 0.045 Uiso 1 1 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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables 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
C005 S001 C007 90.8(2) .
C002 C002 C003 127.4(5) 5_765
C002 C002 C008 126.2(5) 5_765
C003 C002 C008 106.4(3) .
C005 C003 C002 109.9(4) .
C005 C003 C006 112.5(4) .
C006 C003 C002 137.6(4) .
H00A C004 H00B 109.2 .
C005 C004 H00A 111.3 .
C005 C004 H00B 111.3 .
C005 C004 C008 102.2(3) .
C008 C004 H00A 111.3 .
C008 C004 H00B 111.3 .
C003 C005 S001 112.2(3) .
C003 C005 C004 114.0(4) .
C004 C005 S001 133.8(3) .
C003 C006 H006 124.2 .
C007 C006 C003 111.6(4) .
C007 C006 H006 124.2 .
S001 C007 H007 123.5 .
C006 C007 S001 112.9(3) .
C006 C007 H007 123.5 .
C002 C008 C004 107.5(3) .
C002 C008 H00C 110.2 .
C002 C008 H00D 110.2 .
C004 C008 H00C 110.2 .
C004 C008 H00D 110.2 .
H00C C008 H00D 108.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S001 C005 1.719(4) .
S001 C007 1.730(4) .
C002 C002 1.344(8) 5_765
C002 C003 1.462(6) .
C002 C008 1.527(5) .
C003 C005 1.370(6) .
C003 C006 1.434(6) .
C004 H00A 0.9900 .
C004 H00B 0.9900 .
C004 C005 1.497(6) .
C004 C008 1.546(5) .
C006 H006 0.9500 .
C006 C007 1.356(6) .
C007 H007 0.9500 .
C008 H00C 0.9900 .
C008 H00D 0.9900 .
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
C002 C002 C003 C005 179.9(5) 5_765
C002 C002 C003 C006 -0.1(9) 5_765
C002 C002 C008 C004 -179.3(5) 5_765
C002 C003 C005 S001 179.8(3) .
C002 C003 C005 C004 -1.1(5) .
C002 C003 C006 C007 -179.9(4) .
C003 C002 C008 C004 0.1(4) .
C003 C006 C007 S001 0.1(5) .
C005 S001 C007 C006 -0.1(3) .
C005 C003 C006 C007 0.1(5) .
C005 C004 C008 C002 -0.7(4) .
C006 C003 C005 S001 -0.1(4) .
C006 C003 C005 C004 178.9(3) .
C007 S001 C005 C003 0.1(3) .
C007 S001 C005 C004 -178.7(4) .
C008 C002 C003 C005 0.6(4) .
C008 C002 C003 C006 -179.5(4) .
C008 C004 C005 S001 179.9(3) .
C008 C004 C005 C003 1.1(5) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 118485439
