Annulated Thienyl-Vinylene-Thienyl Building Blocks for π-Conjugated Copolymers: Ring Dimensions and Isomeric Structure Effects on π-Conjugation Length and Charge Transport
Takai, Atsuro; Chen, Zhihua; Yu, Xinge; Zhou, Nanjia; Marks, Tobin J.; Facchetti, Antonio; Chemistry of Materials 28 (2016) 5772–; doi:10.1021/acs.chemmater.6b02007

data_4003279
_publ_section_title
;
 Annulated Thienyl-Vinylene-Thienyl Building Blocks for \p-Conjugated
 Copolymers: Ring Dimensions and Isomeric Structure Effects on
 \p-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       '\w and \f 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 \l/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/[\s^2^(Fo^2^)+(0.0804P)^2^+3.4768P] where P=(Fo^2^+2Fc^2^)/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 > 2\s(I)'
_cod_data_source_file            cm6b02007_si_003.cif
_cod_data_source_block           n3109
_cod_database_code               4003279
_shelxl_version_number           2013-3
_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)
;
_shelx_res_checksum              76998
_shelx_hkl_checksum              64363