Design, synthesis, chemical stability, packing, cyclic voltammetry, ionisation potential, and charge transport of [1]benzothieno[3,2-b][1]benzothiophene derivatives
Christian Ruzie; Jolanta Karpinska; Anne Laurent; Lionel Sanguinet; Simon Hunter; Thomas D. Anthopoulos; Vincent Lemaur; Jerome Cornil; Alan R. Kennedy; Oliver Fenwick; Paolo Samori; Guillaume Schweicher; Basab Chattopadhyay; Yves Henri Geerts; Journal of Materials Chemistry C 4 (2016) 4863–4879; doi:10.1039/C6TC01409G

data_7234776
_publ_section_title
;
 Design, synthesis, chemical stability, packing, cyclic voltammetry,
 ionisation potential, and charge transport of
 [1]benzothieno[3,2-b][1]benzothiophene derivatives
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              4863
_journal_page_last               4879
_journal_paper_doi               10.1039/C6TC01409G
_journal_volume                  4
_journal_year                    2016
_chemical_formula_sum            'C30 H40 O2 S2'
_chemical_formula_weight         496.74
_chemical_melting_point          445
_chemical_name_systematic
;
 2,7-dioctyloxy-[1]benzothieno[3,2,b]benzothiophene
;
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                94.482(4)
_cell_angle_beta                 92.994(5)
_cell_angle_gamma                105.696(5)
_cell_formula_units_Z            2
_cell_length_a                   5.5225(4)
_cell_length_b                   8.0712(4)
_cell_length_c                   31.0578(15)
_cell_measurement_reflns_used    4113
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      28.7153
_cell_measurement_theta_min      3.0509
_cell_volume                     1324.76(14)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur E'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_sigmaI/netI    0.0914
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            10939
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         3.06
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             536
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         5633
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0939
_refine_ls_R_factor_gt           0.0537
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0296P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.1040
_reflns_number_gt                4012
_reflns_number_total             5633
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            J-Mater-Chem-C-2016-4-4863.cif
_cod_data_source_block           jb_away_cr781
_cod_original_cell_volume        1324.76(13)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7234776