#------------------------------------------------------------------------------
#$Date: 2019-10-31 12:04:04 +0200 (Thu, 31 Oct 2019) $
#$Revision: 220594 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/48/7234892.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_7234892
loop_
_publ_author_name
'Gilles H. Roche'
'Yu-Tang Tsai'
'Simon Clevers'
'Damien Thuau'
'Frederic Castet'
'Yves H. Geerts'
'Joel J. E. Moreau'
'Guillaume Wantz'
'Olivier J. Dautel'
_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 H32 O2 S2'
_chemical_formula_sum            'C26 H32 O2 S2'
_chemical_formula_weight         440.67
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'I 1 2/a 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 92.829(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4460(3)
_cell_length_b                   5.58942(19)
_cell_length_c                   50.2534(15)
_cell_measurement_reflns_used    7683
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.8350
_cell_measurement_theta_min      2.4330
_cell_volume                     2369.48(14)
_computing_cell_refinement       'USER DEFINED CELL REFINEMENT'
_computing_data_collection       'USER DEFINED DATA COLLECTION'
_computing_data_reduction        'USER DEFINED DATA REDUCTION'
_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    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measurement_device       'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_device_type  Unknown
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.028
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       65
_diffrn_reflns_limit_l_min       -63
_diffrn_reflns_number            20985
_diffrn_reflns_theta_full        25.119
_diffrn_reflns_theta_max         27.910
_diffrn_reflns_theta_min         1.623
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.244
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.18
_refine_diff_density_min         -0.21
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0996
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2345
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0357
_refine_ls_shift/su_max          0.0049566
_refine_ls_shift/su_mean         0.0001830
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 -0.491 -9.23 -5.22 -4.37 -3.11 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0303
_refine_ls_wR_factor_gt          0.0272
_refine_ls_wR_factor_ref         0.0272
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              7
_reflns_limit_k_min              0
_reflns_limit_l_max              65
_reflns_limit_l_min              0
_reflns_number_gt                2345
_reflns_number_total             2631
_reflns_threshold_expression     I>2.0σ(I)
_cod_data_source_file            J-Mater-Chem-C-2016-4-6742.cif
_cod_data_source_block           2
_cod_original_cell_volume        2369.48(7)
_cod_original_sg_symbol_H-M      'I 1 2/a 1 '
_cod_database_code               7234892
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,y+1/2,z+1/2
-x+1/2,-y+1/2,-z+1/2
-x+1/2,y,-z
x+1/2,-y,z
-x+1,y+1/2,-z+1/2
x+1,-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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
S1 S 0.85631(4) 0.54048(5) 0.731553(5) 0.0479 1.0000 Uani . . . . . .
C2 C 0.76031(12) 0.3714(2) 0.70633(2) 0.0403 1.0000 Uani . . . . . .
C3 C 0.68475(12) 0.16708(19) 0.71613(2) 0.0383 1.0000 Uani . . . . . .
C4 C 0.70708(11) 0.15724(18) 0.74454(2) 0.0373 1.0000 Uani . . . . . .
C5 C 0.60107(14) 0.0178(2) 0.69809(2) 0.0489 1.0000 Uani . . . . . .
C6 C 0.59300(15) 0.0760(3) 0.67142(2) 0.0564 1.0000 Uani . . . . . .
C7 C 0.66676(14) 0.2804(2) 0.66163(2) 0.0515 1.0000 Uani . . . . . .
C8 C 0.75183(14) 0.4286(2) 0.67932(2) 0.0485 1.0000 Uani . . . . . .
H81 H 0.7966 0.5684 0.6732 0.0566 1.0000 Uiso R . . . . .
C9 C 0.65725(17) 0.3397(3) 0.63216(2) 0.0645 1.0000 Uani . . . . . .
C10 C 0.78519(17) 0.2174(3) 0.61682(2) 0.0627 1.0000 Uani . . . . . .
C11 C 0.79089(18) 0.3033(3) 0.58815(2) 0.0704 1.0000 Uani . . . . . .
C12 C 0.92304(19) 0.1910(4) 0.57321(3) 0.0783 1.0000 Uani . . . . . .
C13 C 0.9407(2) 0.3031(4) 0.54576(3) 0.0894 1.0000 Uani . . . . . .
C14 C 1.0786(2) 0.2027(5) 0.53183(3) 0.1032 1.0000 Uani . . . . . .
O15 O 1.09751(18) 0.3148(3) 0.50706(3) 0.1308 1.0000 Uani . . . . . .
H142 H 1.1766 0.2210 0.5425 0.1208 1.0000 Uiso R . . . . .
H141 H 1.0566 0.0351 0.5284 0.1208 1.0000 Uiso R . . . . .
H132 H 0.9507 0.4724 0.5474 0.1063 1.0000 Uiso R . . . . .
H131 H 0.8393 0.2705 0.5343 0.1057 1.0000 Uiso R . . . . .
H121 H 1.0210 0.2101 0.5830 0.0902 1.0000 Uiso R . . . . .
H122 H 0.8973 0.0254 0.5713 0.0909 1.0000 Uiso R . . . . .
H112 H 0.7973 0.4737 0.5877 0.0828 1.0000 Uiso R . . . . .
H111 H 0.6860 0.2705 0.5783 0.0835 1.0000 Uiso R . . . . .
H101 H 0.8856 0.2448 0.6256 0.0726 1.0000 Uiso R . . . . .
H102 H 0.7640 0.0497 0.6166 0.0749 1.0000 Uiso R . . . . .
H92 H 0.6591 0.5079 0.6301 0.0758 1.0000 Uiso R . . . . .
H91 H 0.5471 0.2958 0.6243 0.0771 1.0000 Uiso R . . . . .
H61 H 0.5279 -0.0243 0.6590 0.0680 1.0000 Uiso R . . . . .
H51 H 0.5503 -0.1240 0.7034 0.0579 1.0000 Uiso R . . . . .
H151 H 1.0791 0.4571 0.5087 0.1951 0.5000 Uiso R . . . . .
H152 H 1.1879 0.3470 0.5034 0.1947 0.5000 Uiso R . . . . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C4 4_656 S1 . C2 . 90.57(5) yes
S1 . C2 . C3 . 112.73(8) yes
S1 . C2 . C8 . 125.62(9) yes
C3 . C2 . C8 . 121.62(10) yes
C2 . C3 . C4 . 109.88(9) yes
C2 . C3 . C5 . 118.71(10) yes
C4 . C3 . C5 . 131.38(10) yes
C3 . C4 . S1 4_656 133.19(8) yes
C3 . C4 . C4 4_656 114.40(11) yes
S1 4_656 C4 . C4 4_656 112.39(10) yes
C3 . C5 . C6 . 119.27(12) yes
C3 . C5 . H51 . 122.5 no
C6 . C5 . H51 . 118.2 no
C5 . C6 . C7 . 122.17(12) yes
C5 . C6 . H61 . 118.8 no
C7 . C6 . H61 . 119.0 no
C6 . C7 . C8 . 119.07(10) yes
C6 . C7 . C9 . 121.18(12) yes
C8 . C7 . C9 . 119.74(12) yes
C2 . C8 . C7 . 119.15(11) yes
C2 . C8 . H81 . 121.0 no
C7 . C8 . H81 . 119.7 no
C7 . C9 . C10 . 113.11(11) yes
C7 . C9 . H92 . 109.0 no
C10 . C9 . H92 . 112.0 no
C7 . C9 . H91 . 109.1 no
C10 . C9 . H91 . 110.7 no
H92 . C9 . H91 . 102.4 no
C9 . C10 . C11 . 113.25(12) yes
C9 . C10 . H101 . 109.5 no
C11 . C10 . H101 . 108.5 no
C9 . C10 . H102 . 108.0 no
C11 . C10 . H102 . 108.3 no
H101 . C10 . H102 . 109.1 no
C10 . C11 . C12 . 113.43(14) yes
C10 . C11 . H112 . 110.0 no
C12 . C11 . H112 . 111.0 no
C10 . C11 . H111 . 109.8 no
C12 . C11 . H111 . 109.4 no
H112 . C11 . H111 . 102.7 no
C11 . C12 . C13 . 112.64(16) yes
C11 . C12 . H121 . 109.9 no
C13 . C12 . H121 . 107.6 no
C11 . C12 . H122 . 106.5 no
C13 . C12 . H122 . 109.7 no
H121 . C12 . H122 . 110.6 no
C12 . C13 . C14 . 112.39(18) yes
C12 . C13 . H132 . 109.9 no
C14 . C13 . H132 . 110.2 no
C12 . C13 . H131 . 108.5 no
C14 . C13 . H131 . 108.6 no
H132 . C13 . H131 . 107.1 no
C13 . C14 . O15 . 111.77(19) yes
C13 . C14 . H142 . 111.3 no
O15 . C14 . H142 . 108.2 no
C13 . C14 . H141 . 107.4 no
O15 . C14 . H141 . 107.6 no
H142 . C14 . H141 . 110.6 no
C14 . O15 . H151 . 108.4 no
C14 . O15 . H152 . 116.6 no
H151 . O15 . H152 . 89.6 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 . C4 4_656 1.7365(10) yes
S1 . C2 . 1.7481(11) yes
C2 . C3 . 1.4092(15) yes
C2 . C8 . 1.3925(15) yes
C3 . C4 . 1.4318(14) yes
C3 . C5 . 1.3980(16) yes
C4 . C4 4_656 1.365(2) yes
C5 . C6 . 1.3777(16) yes
C5 . H51 . 0.947 no
C6 . C7 . 1.4022(19) yes
C6 . H61 . 0.987 no
C7 . C8 . 1.3891(18) yes
C7 . C9 . 1.5158(16) yes
C8 . H81 . 0.928 no
C9 . C10 . 1.5202(18) yes
C9 . H92 . 0.946 no
C9 . H91 . 1.022 no
C10 . C11 . 1.5217(16) yes
C10 . H101 . 0.948 no
C10 . H102 . 0.955 no
C11 . C12 . 1.512(2) yes
C11 . H112 . 0.954 no
C11 . H111 . 1.010 no
C12 . C13 . 1.529(2) yes
C12 . H121 . 0.948 no
C12 . H122 . 0.955 no
C13 . C14 . 1.497(3) yes
C13 . H132 . 0.954 no
C13 . H131 . 1.024 no
C14 . O15 . 1.410(2) yes
C14 . H142 . 0.970 no
C14 . H141 . 0.969 no
O15 . H151 . 0.815 no
O15 . H152 . 0.815 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
O15 . H151 . O15 2_766 134.02(11) 0.815 2.088 2.718(2) yes
O15 . H152 . O15 5_756 161.706(16) 0.815 1.920 2.705(2) yes
