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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/4/00/32/4003279.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_4003279
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         'C16 H16 S2'
_chemical_formula_sum            'C16 H16 S2'
_chemical_formula_weight         272.41
_space_group_crystal_system      orthorhombic
_space_group_IT_number           54
_space_group_name_Hall           '-P 2a 2ac'
_space_group_name_H-M_alt        'P c c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2013-10-01
_audit_creation_method
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.031(4)
_cell_length_b                   8.6634(14)
_cell_length_c                   6.8845(10)
_cell_measurement_reflns_used    881
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      57.378
_cell_measurement_theta_min      4.013
_cell_volume                     1314.0(4)
_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
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      99.99
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.787
_diffrn_measured_fraction_theta_max 0.995
_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  0.0643
_diffrn_reflns_av_unetI/netI     0.0816
_diffrn_reflns_Laue_measured_fraction_full 0.787
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            3653
_diffrn_reflns_point_group_measured_fraction_full 0.787
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         59.055
_diffrn_reflns_theta_min         4.013
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    3.467
_exptl_absorpt_correction_T_max  0.7516
_exptl_absorpt_correction_T_min  0.4637
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1236 before and 0.0774 after correction.
The Ratio of minimum to maximum transmission is 0.6170.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_description       plate
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.343
_exptl_crystal_size_mid          0.095
_exptl_crystal_size_min          0.048
_refine_diff_density_max         0.726
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.186
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         945
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.186
_refine_ls_R_factor_all          0.1107
_refine_ls_R_factor_gt           0.0988
_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)+(0.0804P)²+3.4768P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2546
_refine_ls_wR_factor_ref         0.2626
_reflns_Friedel_coverage         0.000
_reflns_number_gt                764
_reflns_number_total             945
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cm6b02007_si_003.cif
_cod_data_source_block           n3109
_cod_database_code               4003279
_shelxl_version_number           2013-3
_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   0.851
_shelx_estimated_absorpt_t_min   0.383
_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:
 C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2)
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z'
'x+1/2, -y, -z+1/2'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z'
'-x-1/2, y, z-1/2'
'x, -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
_atom_site_refinement_flags_adp
S1 S 0.70229(11) 0.2250(2) 0.1498(3) 0.0847(10) Uani 1 1 d . .
C1 C 0.6595(4) 0.1312(9) -0.0228(11) 0.085(3) Uani 1 1 d . .
H1 H 0.6759 0.0825 -0.1347 0.102 Uiso 1 1 calc R U
C2 C 0.6008(4) 0.1353(8) 0.0196(10) 0.072(2) Uani 1 1 d . .
H2 H 0.5706 0.0906 -0.0614 0.086 Uiso 1 1 calc R U
C3 C 0.5866(4) 0.2131(8) 0.1989(10) 0.069(2) Uani 1 1 d . .
C4 C 0.6385(4) 0.2677(8) 0.2848(11) 0.075(2) Uani 1 1 d . .
C5 C 0.6419(4) 0.3470(10) 0.4783(10) 0.082(2) Uani 1 1 d . .
H5A H 0.6651 0.4443 0.4654 0.099 Uiso 1 1 calc R U
H5B H 0.6633 0.2799 0.5723 0.099 Uiso 1 1 calc R U
C6 C 0.5783(3) 0.3822(8) 0.5534(10) 0.073(2) Uani 1 1 d . .
H6A H 0.5634 0.4780 0.4910 0.087 Uiso 1 1 calc R U
H6B H 0.5804 0.4010 0.6951 0.087 Uiso 1 1 calc R U
C7 C 0.5330(4) 0.2524(7) 0.5143(9) 0.069(2) Uani 1 1 d . .
H7A H 0.4929 0.2800 0.5690 0.083 Uiso 1 1 calc R U
H7B H 0.5470 0.1564 0.5781 0.083 Uiso 1 1 calc R U
C8 C 0.5273(3) 0.2258(7) 0.2945(10) 0.066(2) Uani 1 1 d . .
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
C1 S1 C4 91.6(4) .
S1 C1 H1 124.2 .
C2 C1 S1 111.7(6) .
C2 C1 H1 124.2 .
C1 C2 H2 122.9 .
C1 C2 C3 114.3(8) .
C3 C2 H2 122.9 .
C2 C3 C8 127.7(8) .
C4 C3 C2 110.5(7) .
C4 C3 C8 121.6(7) .
C3 C4 S1 111.9(6) .
C3 C4 C5 125.6(8) .
C5 C4 S1 122.4(7) .
C4 C5 H5A 109.6 .
C4 C5 H5B 109.6 .
C4 C5 C6 110.3(7) .
H5A C5 H5B 108.1 .
C6 C5 H5A 109.6 .
C6 C5 H5B 109.6 .
C5 C6 H6A 109.0 .
C5 C6 H6B 109.0 .
C5 C6 C7 113.1(6) .
H6A C6 H6B 107.8 .
C7 C6 H6A 109.0 .
C7 C6 H6B 109.0 .
C6 C7 H7A 109.7 .
C6 C7 H7B 109.7 .
C6 C7 C8 109.8(6) .
H7A C7 H7B 108.2 .
C8 C7 H7A 109.7 .
C8 C7 H7B 109.7 .
C3 C8 C7 112.3(7) .
C8 C8 C3 126.1(9) 4_655
C8 C8 C7 121.5(9) 4_655
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C1 1.720(9) .
S1 C4 1.725(8) .
C1 H1 0.9500 .
C1 C2 1.328(12) .
C2 H2 0.9500 .
C2 C3 1.441(10) .
C3 C4 1.371(11) .
C3 C8 1.469(11) .
C4 C5 1.501(11) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C5 C6 1.524(11) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C6 C7 1.527(10) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C7 C8 1.536(9) .
C8 C8 1.348(15) 4_655
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_4
S1 C1 C2 C3 -1.1(8) .
S1 C4 C5 C6 174.8(5) .
C1 S1 C4 C3 -0.6(6) .
C1 S1 C4 C5 176.0(7) .
C1 C2 C3 C4 0.7(9) .
C1 C2 C3 C8 -174.3(7) .
C2 C3 C4 S1 0.0(7) .
C2 C3 C4 C5 -176.4(7) .
C2 C3 C8 C7 155.2(6) .
C2 C3 C8 C8 -29.2(8) 4_655
C3 C4 C5 C6 -9.1(10) .
C4 S1 C1 C2 1.0(6) .
C4 C3 C8 C7 -19.3(9) .
C4 C3 C8 C8 156.2(5) 4_655
C4 C5 C6 C7 39.8(8) .
C5 C6 C7 C8 -60.9(8) .
C6 C7 C8 C3 48.6(8) .
C6 C7 C8 C8 -127.2(5) 4_655
C8 C3 C4 S1 175.4(5) .
C8 C3 C4 C5 -1.0(11) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 118485483
