#------------------------------------------------------------------------------
#$Date: 2019-11-28 17:06:08 +0200 (Thu, 28 Nov 2019) $
#$Revision: 244153 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/83/7238381.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_7238381
loop_
_publ_author_name
'Nishinaga, Tohru'
'Miyata, Toshihiko'
'Tateno, Masaki'
'Koizumi, Masahide'
'Takase, Masayoshi'
'Iyoda, Masahiko'
'Kobayashi, Norihito'
'Kunugi, Yoshihito'
_publ_section_title
;
 Synthesis and structural, electronic, optical and FET properties of
 thiophene--pyrrole mixed hexamers end-capped with phenyl and
 pentafluorophenyl groups
;
_journal_issue                   38
_journal_name_full               'Journal of Materials Chemistry'
_journal_page_first              14959
_journal_paper_doi               10.1039/c1jm12966j
_journal_volume                  21
_journal_year                    2011
_chemical_formula_sum            'C48 H43 F5 N2 S4'
_chemical_formula_weight         871.08
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                104.347(4)
_cell_angle_beta                 93.216(4)
_cell_angle_gamma                90.447(4)
_cell_formula_units_Z            1
_cell_length_a                   5.5928(11)
_cell_length_b                   10.505(2)
_cell_length_c                   18.392(4)
_cell_measurement_temperature    293(2)
_cell_volume                     1045.0(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.948
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_device_type  'CCD aarea detector'
_diffrn_measurement_method       'phi and 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  0.0124
_diffrn_reflns_av_sigmaI/netI    0.0217
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3852
_diffrn_reflns_theta_full        23.29
_diffrn_reflns_theta_max         23.29
_diffrn_reflns_theta_min         1.14
_exptl_absorpt_coefficient_mu    0.287
_exptl_absorpt_correction_type   empirical
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             454
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.328
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         2855
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.328
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0461
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1525
_refine_ls_wR_factor_ref         0.1632
_reflns_number_gt                2467
_reflns_number_total             2855
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1jm12966j.txt
_cod_data_source_block           5a
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7238381
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S -0.81535(14) 0.19093(8) 0.01999(5) 0.0640(3) Uani 1 1 d . . .
S2 S 0.25852(14) 0.62914(8) 0.17650(4) 0.0597(3) Uani 1 1 d . . .
N1 N -0.2605(4) 0.3588(2) 0.15531(12) 0.0513(6) Uani 1 1 d . . .
C1 C -0.8961(5) 0.0342(3) 0.02206(16) 0.0574(7) Uani 1 1 d . . .
C2 C -0.7351(6) -0.0125(3) 0.06745(17) 0.0637(8) Uani 1 1 d . . .
H1 H -0.7492 -0.0952 0.0769 0.076 Uiso 1 1 calc R . .
C3 C -0.5458(6) 0.0774(3) 0.09841(16) 0.0626(8) Uani 1 1 d . . .
H2 H -0.4226 0.0595 0.1303 0.075 Uiso 1 1 calc R . .
C4 C -0.5596(5) 0.1919(3) 0.07761(14) 0.0530(7) Uani 1 1 d . . .
C5 C -0.4005(5) 0.3058(3) 0.09010(14) 0.0507(7) Uani 1 1 d . . .
C6 C -0.3605(5) 0.3835(3) 0.04122(15) 0.0559(8) Uani 1 1 d . . .
H3 H -0.4312 0.3713 -0.0071 0.067 Uiso 1 1 calc R . .
C7 C -0.1981(5) 0.4824(3) 0.07597(15) 0.0540(7) Uani 1 1 d . . .
H4 H -0.1400 0.5476 0.0550 0.065 Uiso 1 1 calc R . .
C8 C -0.1367(5) 0.4679(3) 0.14723(15) 0.0514(7) Uani 1 1 d . . .
C9 C 0.0214(5) 0.5527(3) 0.20524(15) 0.0530(7) Uani 1 1 d . . .
C10 C 0.0124(6) 0.5916(3) 0.28154(16) 0.0632(8) Uani 1 1 d . . .
H5 H -0.1013 0.5598 0.3080 0.076 Uiso 1 1 calc R . .
C11 C 0.1913(6) 0.6840(3) 0.31591(16) 0.0658(9) Uani 1 1 d . . .
H6 H 0.2080 0.7190 0.3676 0.079 Uiso 1 1 calc R . .
C12 C 0.3396(6) 0.7184(3) 0.26694(15) 0.0571(7) Uani 1 1 d . . .
C13 C 0.5389(6) 0.8150(3) 0.28339(16) 0.0598(8) Uani 1 1 d . A .
C14 C 0.6008(7) 0.8863(3) 0.35652(19) 0.0745(10) Uani 1 1 d . . .
C15 C 0.7952(8) 0.9744(4) 0.3732(3) 0.0938(13) Uani 1 1 d . A .
C16 C 0.9298(8) 0.9932(4) 0.3161(3) 0.0924(13) Uani 1 1 d . . .
C17 C 0.8667(7) 0.9272(4) 0.2438(2) 0.0796(10) Uani 1 1 d . A .
C18 C 0.6752(6) 0.8404(3) 0.2279(2) 0.0674(9) Uani 1 1 d . . .
F1 F 0.4544(7) 0.8667(4) 0.41476(18) 0.0817(11) Uani 0.50 1 d P A 1
F2 F 0.8255(9) 1.0276(5) 0.4469(2) 0.1040(15) Uani 0.50 1 d P A 1
F3 F 1.0966(7) 1.0706(4) 0.3370(3) 0.1001(14) Uani 0.50 1 d P A 1
F4 F 0.9779(7) 0.9453(4) 0.1931(2) 0.0810(11) Uani 0.50 1 d P A 1
F5 F 0.6142(6) 0.7786(4) 0.15835(18) 0.0672(9) Uani 0.50 1 d P A 1
C19 C -0.2516(5) 0.3087(3) 0.22295(15) 0.0544(7) Uani 1 1 d . . .
H7 H -0.1065 0.3418 0.2534 0.065 Uiso 1 1 calc R . .
H8 H -0.2448 0.2136 0.2083 0.065 Uiso 1 1 calc R . .
C20 C -0.4666(5) 0.3482(3) 0.26990(15) 0.0557(7) Uani 1 1 d . . .
H9 H -0.4777 0.4432 0.2831 0.067 Uiso 1 1 calc R . .
H10 H -0.6116 0.3118 0.2404 0.067 Uiso 1 1 calc R . .
C21 C -0.4477(5) 0.3002(3) 0.34076(15) 0.0617(8) Uani 1 1 d . . .
H11 H -0.2952 0.3304 0.3675 0.074 Uiso 1 1 calc R . .
H12 H -0.4484 0.2049 0.3270 0.074 Uiso 1 1 calc R . .
C22 C -0.6466(6) 0.3456(3) 0.39350(16) 0.0667(8) Uani 1 1 d . . .
H13 H -0.6465 0.4409 0.4075 0.080 Uiso 1 1 calc R . .
H14 H -0.7995 0.3150 0.3671 0.080 Uiso 1 1 calc R . .
C23 C -0.6221(7) 0.2963(4) 0.46398(17) 0.0802(10) Uani 1 1 d . . .
H15 H -0.6194 0.2011 0.4499 0.096 Uiso 1 1 calc R . .
H16 H -0.4703 0.3280 0.4907 0.096 Uiso 1 1 calc R . .
C24 C -0.8201(8) 0.3388(5) 0.5160(2) 0.1013(14) Uani 1 1 d . . .
H17 H -0.8377 0.4322 0.5251 0.152 Uiso 1 1 calc R . .
H18 H -0.7821 0.3162 0.5627 0.152 Uiso 1 1 calc R . .
H19 H -0.9673 0.2952 0.4934 0.152 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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
_geom_angle_site_symmetry_3
C1 S1 C4 92.86(14) . .
C9 S2 C12 92.77(14) . .
C8 N1 C5 109.3(2) . .
C8 N1 C19 125.5(2) . .
C5 N1 C19 125.1(2) . .
C2 C1 C1 128.0(4) . 2_355
C2 C1 S1 110.1(2) . .
C1 C1 S1 121.9(3) 2_355 .
C1 C2 C3 113.1(3) . .
C4 C3 C2 113.9(3) . .
C3 C4 C5 133.2(3) . .
C3 C4 S1 109.9(2) . .
C5 C4 S1 116.8(2) . .
C6 C5 N1 106.6(3) . .
C6 C5 C4 127.7(3) . .
N1 C5 C4 125.7(2) . .
C7 C6 C5 108.6(3) . .
C6 C7 C8 108.3(3) . .
N1 C8 C7 107.1(3) . .
N1 C8 C9 125.2(2) . .
C7 C8 C9 127.7(3) . .
C10 C9 C8 131.9(3) . .
C10 C9 S2 110.4(2) . .
C8 C9 S2 117.59(19) . .
C9 C10 C11 113.2(3) . .
C12 C11 C10 114.2(3) . .
C11 C12 C13 128.5(3) . .
C11 C12 S2 109.4(2) . .
C13 C12 S2 122.1(2) . .
C18 C13 C14 116.3(3) . .
C18 C13 C12 122.5(3) . .
C14 C13 C12 121.2(3) . .
C13 C14 C15 121.8(4) . .
C13 C14 F1 117.4(3) . .
C15 C14 F1 120.8(3) . .
F2 C15 C16 129.1(5) . .
F2 C15 C14 111.2(5) . .
C16 C15 C14 119.7(4) . .
F3 C16 C17 126.6(6) . .
F3 C16 C15 114.1(5) . .
C17 C16 C15 119.2(4) . .
F4 C17 C16 120.1(4) . .
F4 C17 C18 119.1(4) . .
C16 C17 C18 120.7(4) . .
F5 C18 C17 120.3(4) . .
F5 C18 C13 117.4(3) . .
C17 C18 C13 122.3(3) . .
N1 C19 C20 112.7(2) . .
C21 C20 C19 111.5(2) . .
C20 C21 C22 114.3(3) . .
C23 C22 C21 113.1(3) . .
C24 C23 C22 113.5(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C1 1.714(3) .
S1 C4 1.730(3) .
S2 C9 1.719(3) .
S2 C12 1.729(3) .
N1 C8 1.378(4) .
N1 C5 1.385(4) .
N1 C19 1.465(3) .
C1 C2 1.369(4) .
C1 C1 1.455(6) 2_355
C2 C3 1.410(5) .
C3 C4 1.351(4) .
C4 C5 1.449(4) .
C5 C6 1.382(4) .
C6 C7 1.379(4) .
C7 C8 1.381(4) .
C8 C9 1.458(4) .
C9 C10 1.365(4) .
C10 C11 1.397(5) .
C11 C12 1.368(4) .
C12 C13 1.468(5) .
C13 C18 1.383(5) .
C13 C14 1.391(4) .
C14 C15 1.393(6) .
C14 F1 1.437(5) .
C15 F2 1.334(5) .
C15 C16 1.378(6) .
C16 F3 1.213(5) .
C16 C17 1.362(6) .
C17 F4 1.203(5) .
C17 C18 1.372(5) .
C18 F5 1.308(5) .
C19 C20 1.520(4) .
C20 C21 1.508(4) .
C21 C22 1.519(4) .
C22 C23 1.510(4) .
C23 C24 1.502(5) .
