The role of H-bonds in the solid state organization of [1]benzothieno[3,2-b][1]benzothiophene (BTBT) structures: bis(hydroxy-hexyl)-BTBT, as a functional derivative offering efficient air stable organic field effect transistors (OFETs)
Gilles H. Roche; Yu-Tang Tsai; Simon Clevers; Damien Thuau; Frederic Castet; Yves H. Geerts; Joel J. E. Moreau; Guillaume Wantz; Olivier J. Dautel; Journal of Materials Chemistry C 4 (2016) 6742–6749; doi:10.1039/C6TC01814A

data_7234891
_publ_section_title
;
 The role of H-bonds in the solid state organization of
 [1]benzothieno[3,2-b][1]benzothiophene (BTBT) structures:
 bis(hydroxy-hexyl)-BTBT, as a functional derivative offering efficient
 air stable organic field effect transistors (OFETs)
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              6742
_journal_page_last               6749
_journal_paper_doi               10.1039/C6TC01814A
_journal_volume                  4
_journal_year                    2016
_chemical_absolute_configuration .
_chemical_formula_moiety         'C26 H26 Br2 O2 S2'
_chemical_formula_sum            'C26 H26 Br2 O2 S2'
_chemical_formula_weight         594.41
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     iterative
_cell_angle_alpha                90
_cell_angle_beta                 97.654(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.0077(7)
_cell_length_b                   15.6418(6)
_cell_length_c                   8.2319(3)
_cell_measurement_reflns_used    9412
_cell_measurement_temperature    175
_cell_measurement_theta_max      68.2130
_cell_measurement_theta_min      2.3150
_cell_volume                     2425.66(16)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      175
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0143
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
;
  1 omega  -89.00    2.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  126.0000   60.0000 91

  2 omega  -50.00   37.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   38.0000  -30.0000 87

  3 omega -104.00  -11.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -38.0000  150.0000 93

  4 omega   19.00   90.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       35.0065 -126.0000 -150.0000 71

  5 omega  101.00  171.00   1.0000   20.0100
omega____ theta____ kappa____ phi______ frames
    -      100.0000  112.0000   30.0000 70

  6 omega   32.00  120.00   1.0000   20.0100
omega____ theta____ kappa____ phi______ frames
    -      100.0000  -61.0000  120.0000 88

  7 omega   30.00   98.00   1.0000   20.0100
omega____ theta____ kappa____ phi______ frames
    -      100.0000  -45.0000  120.0000 68

  8 omega   29.00  115.00   1.0000   20.0100
omega____ theta____ kappa____ phi______ frames
    -      100.0000 -112.0000 -120.0000 86

  9 omega   30.00   98.00   1.0000   20.0100
omega____ theta____ kappa____ phi______ frames
    -      100.0000  -45.0000 -120.0000 68

 10 omega   29.00   91.00   1.0000   20.0100
omega____ theta____ kappa____ phi______ frames
    -      100.0000  -30.0000    0.0000 62

 11 omega   74.00  171.00   1.0000   20.0100
omega____ theta____ kappa____ phi______ frames
    -      100.0000   30.0000 -150.0000 97

 12 omega   30.00  109.00   1.0000   20.0100
omega____ theta____ kappa____ phi______ frames
    -      100.0000  -95.0000  120.0000 79

 13 omega   30.00   98.00   1.0000   20.0100
omega____ theta____ kappa____ phi______ frames
    -      100.0000  -45.0000  -60.0000 68

 14 omega   29.00  115.00   1.0000   20.0100
omega____ theta____ kappa____ phi______ frames
    -      100.0000 -112.0000  120.0000 86

 15 omega   30.00   98.00   1.0000   20.0100
omega____ theta____ kappa____ phi______ frames
    -      100.0000  -45.0000  -30.0000 68

 16 omega   29.00   91.00   1.0000   20.0100
omega____ theta____ kappa____ phi______ frames
    -      100.0000  -30.0000  -30.0000 62

 17 omega   17.00  103.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       35.0065   57.0000    0.0000 86

 18 omega   17.00  103.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       35.0065   57.0000   90.0000 86

 19 omega   -4.00   75.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       35.0065  -99.0000   30.0000 79

 20 omega   17.00  103.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       35.0065   57.0000  -90.0000 86

 21 omega   55.00  126.00   1.0000   20.0100
omega____ theta____ kappa____ phi______ frames
    -      100.0000   15.0000  120.0000 71

 22 omega   55.00   80.00   1.0000   20.0100
omega____ theta____ kappa____ phi______ frames
    -      100.0000   15.0000    0.0000 25

;
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0178461000
_diffrn_orient_matrix_UB_12      0.0937949000
_diffrn_orient_matrix_UB_13      0.0346510000
_diffrn_orient_matrix_UB_21      0.0573290000
_diffrn_orient_matrix_UB_22      -0.0001549000
_diffrn_orient_matrix_UB_23      0.1510904000
_diffrn_orient_matrix_UB_31      0.0555446000
_diffrn_orient_matrix_UB_32      0.0301941000
_diffrn_orient_matrix_UB_33      -0.1075635000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.104
_diffrn_reflns_av_unetI/netI     0.0733
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            16748
_diffrn_reflns_theta_full        66.887
_diffrn_reflns_theta_max         68.252
_diffrn_reflns_theta_min         2.345
_exptl_absorpt_coefficient_mu    6.019
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37005
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_refine_diff_density_max         3.60
_refine_diff_density_min         -2.07
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4035
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1223
_refine_ls_R_factor_gt           0.1194
_refine_ls_shift/su_max          0.0017278
_refine_ls_shift/su_mean         0.0000301
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 67.9 68.8 64.7 23.9 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1133
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1096
_reflns_limit_h_max              22
_reflns_limit_h_min              -22
_reflns_limit_k_max              18
_reflns_limit_k_min              0
_reflns_limit_l_max              9
_reflns_limit_l_min              0
_reflns_number_gt                4035
_reflns_number_total             4386
_reflns_threshold_expression     I>2.0\s(I)
_cod_data_source_file            J-Mater-Chem-C-2016-4-6742.cif
_cod_data_source_block           1
_cod_original_cell_volume        2425.67(9)
_cod_original_sg_symbol_H-M      'P 21/c '
_cod_database_code               7234891