#------------------------------------------------------------------------------
#$Date: 2019-11-22 21:48:53 +0100 (vie 22 de nov de 2019) $
#$Revision: 231485 $
#$URL: svn://www.crystallography.net/cod/cif/4/00/32/4003280.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_4003280
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      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   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2014-02-03
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_cell_angle_alpha                90
_cell_angle_beta                 98.038(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.5548(13)
_cell_length_b                   8.0291(10)
_cell_length_c                   6.8298(9)
_cell_measurement_reflns_used    1156
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.037
_cell_measurement_theta_min      4.230
_cell_volume                     573.11(13)
_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      99.99
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.918
_diffrn_measured_fraction_theta_max 0.964
_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  0.0252
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_Laue_measured_fraction_full 0.918
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            2017
_diffrn_reflns_point_group_measured_fraction_full 0.918
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         65.032
_diffrn_reflns_theta_min         4.230
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    3.911
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.5850
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0632 before and 0.0336 after correction.
The Ratio of minimum to maximum transmission is 0.7773.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_description       block
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.107
_exptl_crystal_size_mid          0.085
_exptl_crystal_size_min          0.028
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     97
_refine_ls_number_reflns         946
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.126
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0378
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0611P)²+0.1304P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.1005
_reflns_Friedel_coverage         0.000
_reflns_number_gt                826
_reflns_number_total             946
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cm6b02007_si_001.cif
_cod_data_source_block           n3294
_cod_database_code               4003280
_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   0.898
_shelx_estimated_absorpt_t_min   0.680
_olex2_refinement_description
;
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, 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
S1 S 0.79815(5) 0.85896(6) 0.15669(7) 0.0310(3) Uani 1 1 d
C2 C 0.6358(2) 0.8886(3) 0.1456(3) 0.0340(6) Uani 1 1 d
H2 H 0.581(3) 0.844(3) 0.043(5) 0.044(8) Uiso 1 1 d
C3 C 0.6049(2) 0.9826(3) 0.2983(3) 0.0322(5) Uani 1 1 d
H3 H 0.520(3) 1.010(4) 0.300(4) 0.049(8) Uiso 1 1 d
C4 C 0.7150(2) 1.0310(3) 0.4290(3) 0.0268(5) Uani 1 1 d
C5 C 0.7430(2) 1.1300(3) 0.6173(4) 0.0366(6) Uani 1 1 d
H5A H 0.708(3) 1.084(4) 0.725(5) 0.062(9) Uiso 1 1 d
H5B H 0.713(3) 1.241(4) 0.593(4) 0.055(9) Uiso 1 1 d
C6 C 0.8898(2) 1.1230(3) 0.6675(3) 0.0301(5) Uani 1 1 d
H6A H 0.927(2) 1.229(4) 0.674(4) 0.030(6) Uiso 1 1 d
H6B H 0.914(3) 1.071(4) 0.795(4) 0.043(7) Uiso 1 1 d
C7 C 0.9387(2) 1.0196(2) 0.5053(3) 0.0228(4) Uani 1 1 d
C8 C 0.8264(2) 0.9743(2) 0.3714(3) 0.0235(5) 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
C2 S1 C8 90.91(10) .
S1 C2 H2 119.7(19) .
C3 C2 S1 112.75(17) .
C3 C2 H2 127.5(19) .
C2 C3 H3 118.6(19) .
C2 C3 C4 111.7(2) .
C4 C3 H3 129.6(19) .
C3 C4 C5 136.8(2) .
C8 C4 C3 112.9(2) .
C8 C4 C5 110.31(19) .
C4 C5 H5A 114(2) .
C4 C5 H5B 108.9(18) .
C4 C5 C6 104.03(18) .
H5A C5 H5B 110(3) .
C6 C5 H5A 108(2) .
C6 C5 H5B 111.7(19) .
C5 C6 H6A 112.3(15) .
C5 C6 H6B 110.2(16) .
H6A C6 H6B 107(2) .
C7 C6 C5 106.81(17) .
C7 C6 H6A 110.2(15) .
C7 C6 H6B 110.0(17) .
C7 C7 C6 126.2(2) 3_776
C7 C7 C8 128.4(2) 3_776
C8 C7 C6 105.40(18) .
C4 C8 S1 111.69(16) .
C4 C8 C7 113.44(18) .
C7 C8 S1 134.84(17) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C2 1.721(3) .
S1 C8 1.7247(19) .
C2 H2 0.91(3) .
C2 C3 1.363(3) .
C3 H3 0.92(3) .
C3 C4 1.417(3) .
C4 C5 1.505(3) .
C4 C8 1.369(3) .
C5 H5A 0.95(4) .
C5 H5B 0.95(3) .
C5 C6 1.540(3) .
C6 H6A 0.94(3) .
C6 H6B 0.96(3) .
C6 C7 1.531(3) .
C7 C7 1.343(4) 3_776
C7 C8 1.439(3) .
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
S1 C2 C3 C4 -0.5(3) . .
C2 S1 C8 C4 0.21(17) . .
C2 S1 C8 C7 177.9(2) . .
C2 C3 C4 C5 -179.5(3) . .
C2 C3 C4 C8 0.7(3) . .
C3 C4 C5 C6 179.5(2) . .
C3 C4 C8 S1 -0.6(2) . .
C3 C4 C8 C7 -178.74(16) . .
C4 C5 C6 C7 -0.1(2) . .
C5 C4 C8 S1 179.62(15) . .
C5 C4 C8 C7 1.4(3) . .
C5 C6 C7 C7 -178.7(3) . 3_776
C5 C6 C7 C8 0.9(2) . .
C6 C7 C8 S1 -179.09(17) . .
C6 C7 C8 C4 -1.5(2) . .
C7 C7 C8 S1 0.5(4) 3_776 .
C7 C7 C8 C4 178.1(2) 3_776 .
C8 S1 C2 C3 0.19(18) . .
C8 C4 C5 C6 -0.7(3) . .
