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#$Date: 2025-08-23 00:12:46 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301866 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/83/7238380.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_7238380
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 H48 N2 S4'
_chemical_formula_weight         781.12
_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                99.104(3)
_cell_angle_beta                 103.488(2)
_cell_angle_gamma                102.840(2)
_cell_formula_units_Z            2
_cell_length_a                   9.7580(12)
_cell_length_b                   12.2984(13)
_cell_length_c                   18.563(2)
_cell_measurement_temperature    293(2)
_cell_volume                     2059.6(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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0368
_diffrn_reflns_av_sigmaI/netI    0.0836
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9385
_diffrn_reflns_theta_full        23.26
_diffrn_reflns_theta_max         23.26
_diffrn_reflns_theta_min         1.16
_exptl_absorpt_coefficient_mu    0.267
_exptl_absorpt_correction_type   empirical
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             828
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     507
_refine_ls_number_reflns         5894
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.991
_refine_ls_R_factor_all          0.1222
_refine_ls_R_factor_gt           0.0550
_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)+(0.0777P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1180
_refine_ls_wR_factor_ref         0.1615
_reflns_number_gt                3295
_reflns_number_total             5894
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1jm12966j.txt
_cod_data_source_block           3a
_cod_original_cell_volume        2059.5(4)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7238380
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
C1 C 0.6376(8) 0.4081(5) -0.2067(3) 0.0809(18) Uani 1 1 d . . .
H1 H 0.6060 0.4359 -0.2496 0.097 Uiso 1 1 calc R . .
C2 C 0.7833(8) 0.4367(5) -0.1690(4) 0.0905(19) Uani 1 1 d . . .
H2 H 0.8505 0.4847 -0.1862 0.109 Uiso 1 1 calc R . .
C3 C 0.5387(7) 0.3384(5) -0.1809(3) 0.0748(16) Uani 1 1 d . . .
H3 H 0.4393 0.3198 -0.2058 0.090 Uiso 1 1 calc R . .
C4 C 0.8314(6) 0.3953(5) -0.1061(3) 0.0780(17) Uani 1 1 d . . .
H4 H 0.9306 0.4166 -0.0805 0.094 Uiso 1 1 calc R . .
C5 C 0.5867(5) 0.2954(4) -0.1177(3) 0.0603(14) Uani 1 1 d . . .
H5 H 0.5190 0.2481 -0.1004 0.072 Uiso 1 1 calc R . .
C6 C 0.7343(5) 0.3222(4) -0.0802(3) 0.0550(13) Uani 1 1 d . . .
C7 C 0.7892(5) 0.2751(4) -0.0148(3) 0.0493(12) Uani 1 1 d . . .
C8 C 0.9254(5) 0.2664(4) 0.0131(3) 0.0649(14) Uani 1 1 d . . .
H6 H 1.0025 0.2956 -0.0060 0.078 Uiso 1 1 calc R . .
C9 C 0.9424(5) 0.2101(5) 0.0729(3) 0.0694(15) Uani 1 1 d . . .
H7 H 1.0311 0.1985 0.0970 0.083 Uiso 1 1 calc R . .
C10 C 0.8161(5) 0.1735(4) 0.0926(2) 0.0490(12) Uani 1 1 d . . .
C11 C 0.7865(5) 0.1101(4) 0.1493(3) 0.0479(12) Uani 1 1 d . . .
C12 C 0.6598(5) 0.0328(4) 0.1488(3) 0.0522(12) Uani 1 1 d . . .
H8 H 0.5718 0.0111 0.1107 0.063 Uiso 1 1 calc R . .
C13 C 0.6866(5) -0.0074(4) 0.2155(3) 0.0520(12) Uani 1 1 d . . .
H9 H 0.6191 -0.0599 0.2297 0.062 Uiso 1 1 calc R . .
C14 C 0.8292(5) 0.0438(4) 0.2566(2) 0.0449(11) Uani 1 1 d . . .
C15 C 1.0207(5) 0.2141(4) 0.2529(3) 0.0595(14) Uani 1 1 d . . .
H10 H 1.0586 0.2448 0.2143 0.071 Uiso 1 1 calc R . .
H11 H 1.0963 0.1881 0.2838 0.071 Uiso 1 1 calc R . .
C16 C 0.9833(6) 0.3079(5) 0.3027(3) 0.0845(18) Uani 1 1 d . . .
H12 H 0.9034 0.3298 0.2720 0.101 Uiso 1 1 calc R . .
H13 H 0.9494 0.2772 0.3424 0.101 Uiso 1 1 calc R . .
C17 C 1.1059(6) 0.4107(5) 0.3383(3) 0.0845(18) Uani 1 1 d . . .
H14 H 1.1372 0.4434 0.2987 0.101 Uiso 1 1 calc R . .
H15 H 1.1873 0.3885 0.3674 0.101 Uiso 1 1 calc R . .
C18 C 1.0697(6) 0.5025(5) 0.3908(3) 0.0855(18) Uani 1 1 d . . .
H16 H 0.9810 0.5179 0.3634 0.103 Uiso 1 1 calc R . .
H17 H 1.0497 0.4725 0.4336 0.103 Uiso 1 1 calc R . .
C19 C 1.1851(7) 0.6110(5) 0.4198(4) 0.103(2) Uani 1 1 d . . .
H18 H 1.2072 0.6402 0.3770 0.123 Uiso 1 1 calc R . .
H19 H 1.2731 0.5963 0.4486 0.123 Uiso 1 1 calc R . .
C20 C 1.1461(7) 0.7006(5) 0.4691(4) 0.114(2) Uani 1 1 d . . .
H20 H 1.2260 0.7688 0.4858 0.171 Uiso 1 1 calc R . .
H21 H 1.1270 0.6734 0.5125 0.171 Uiso 1 1 calc R . .
H22 H 1.0604 0.7171 0.4408 0.171 Uiso 1 1 calc R . .
C21 C 0.9123(5) 0.0271(4) 0.3280(3) 0.0470(12) Uani 1 1 d . . .
C22 C 1.0481(5) 0.0112(4) 0.3468(3) 0.0622(14) Uani 1 1 d . . .
H23 H 1.1055 0.0091 0.3134 0.075 Uiso 1 1 calc R . .
C23 C 1.0937(5) -0.0017(4) 0.4217(3) 0.0586(13) Uani 1 1 d . . .
H24 H 1.1843 -0.0135 0.4425 0.070 Uiso 1 1 calc R . .
C24 C 0.9945(5) 0.0044(4) 0.4608(2) 0.0474(12) Uani 1 1 d . . .
C25 C 0.1392(7) 0.3826(6) -0.2143(4) 0.0868(18) Uani 1 1 d . . .
H25 H 0.1039 0.4027 -0.2599 0.104 Uiso 1 1 calc R . .
C26 C 0.2136(7) 0.4649(5) -0.1498(4) 0.0880(19) Uani 1 1 d . . .
H26 H 0.2298 0.5417 -0.1519 0.106 Uiso 1 1 calc R . .
C27 C 0.1176(6) 0.2688(6) -0.2105(3) 0.0864(18) Uani 1 1 d . . .
H27 H 0.0682 0.2118 -0.2540 0.104 Uiso 1 1 calc R . .
C28 C 0.2646(6) 0.4362(5) -0.0821(3) 0.0723(16) Uani 1 1 d . . .
H28 H 0.3141 0.4936 -0.0388 0.087 Uiso 1 1 calc R . .
C29 C 0.1685(6) 0.2395(5) -0.1427(3) 0.0686(15) Uani 1 1 d . . .
H29 H 0.1525 0.1627 -0.1408 0.082 Uiso 1 1 calc R . .
C30 C 0.2430(5) 0.3221(4) -0.0777(3) 0.0545(13) Uani 1 1 d . . .
C31 C 0.2968(5) 0.2942(4) -0.0038(3) 0.0535(13) Uani 1 1 d . . .
C32 C 0.3725(6) 0.3665(4) 0.0639(3) 0.0684(15) Uani 1 1 d . . .
H30 H 0.4067 0.4451 0.0693 0.082 Uiso 1 1 calc R . .
C33 C 0.3948(6) 0.3127(4) 0.1248(3) 0.0691(15) Uani 1 1 d . . .
H31 H 0.4459 0.3526 0.1742 0.083 Uiso 1 1 calc R . .
C34 C 0.3355(5) 0.1964(4) 0.1064(3) 0.0528(13) Uani 1 1 d . . .
C35 C 0.3214(5) 0.1103(4) 0.1505(3) 0.0506(12) Uani 1 1 d . . .
C36 C 0.2231(5) 0.0023(4) 0.1274(3) 0.0628(14) Uani 1 1 d . . .
H32 H 0.1555 -0.0279 0.0800 0.075 Uiso 1 1 calc R . .
C37 C 0.2429(5) -0.0527(4) 0.1870(3) 0.0627(14) Uani 1 1 d . . .
H33 H 0.1916 -0.1265 0.1861 0.075 Uiso 1 1 calc R . .
C38 C 0.3513(5) 0.0202(4) 0.2478(3) 0.0510(12) Uani 1 1 d . . .
C39 C 0.5236(5) 0.2170(4) 0.2690(3) 0.0546(13) Uani 1 1 d . . .
H34 H 0.5735 0.2487 0.2345 0.066 Uiso 1 1 calc R . .
H35 H 0.5920 0.1891 0.3034 0.066 Uiso 1 1 calc R . .
C40 C 0.4813(5) 0.3120(4) 0.3152(3) 0.0561(13) Uani 1 1 d . . .
H36 H 0.4023 0.3323 0.2825 0.067 Uiso 1 1 calc R . .
H37 H 0.4458 0.2840 0.3553 0.067 Uiso 1 1 calc R . .
C41 C 0.6089(5) 0.4178(4) 0.3501(3) 0.0756(17) Uani 1 1 d . B .
H38 H 0.6911 0.3952 0.3781 0.091 Uiso 1 1 calc R . .
H39 H 0.6378 0.4492 0.3095 0.091 Uiso 1 1 calc R . .
C42 C 0.5784(7) 0.5094(5) 0.4022(3) 0.0856(19) Uani 1 1 d . . .
H40 H 0.4868 0.5230 0.3771 0.103 Uiso 1 1 calc R A 1
H41 H 0.5662 0.4825 0.4473 0.103 Uiso 1 1 calc R A 1
C43 C 0.686(4) 0.611(3) 0.424(2) 0.140(16) Uani 0.50 1 d P B 1
H42 H 0.6858 0.6390 0.3779 0.169 Uiso 0.50 1 calc PR B 1
H43 H 0.7776 0.5909 0.4387 0.169 Uiso 0.50 1 calc PR B 1
C44 C 0.4049(5) -0.0060(4) 0.3211(3) 0.0517(12) Uani 1 1 d . . .
C45 C 0.3996(5) -0.1127(4) 0.3329(3) 0.0645(14) Uani 1 1 d . . .
H44 H 0.3724 -0.1774 0.2937 0.077 Uiso 1 1 calc R . .
C46 C 0.4391(5) -0.1162(4) 0.4099(3) 0.0638(14) Uani 1 1 d . . .
H45 H 0.4392 -0.1840 0.4261 0.077 Uiso 1 1 calc R . .
C47 C 0.4769(5) -0.0142(4) 0.4586(3) 0.0516(12) Uani 1 1 d . . .
N1 N 0.8913(4) 0.1169(3) 0.2162(2) 0.0479(10) Uani 1 1 d . . .
N2 N 0.3986(4) 0.1202(3) 0.2250(2) 0.0464(9) Uani 1 1 d . . .
S1 S 0.67607(13) 0.21075(11) 0.03464(7) 0.0569(4) Uani 1 1 d . . .
S2 S 0.84006(13) 0.02587(11) 0.40415(7) 0.0539(4) Uani 1 1 d . . .
S3 S 0.25657(14) 0.15510(10) 0.00911(7) 0.0577(4) Uani 1 1 d . . .
S4 S 0.46394(13) 0.09116(10) 0.40802(7) 0.0565(4) Uani 1 1 d . . .
C48 C 0.7162(14) 0.6930(12) 0.3955(10) 0.100(5) Uani 0.50 1 d P B 2
H46 H 0.7353 0.6542 0.3513 0.150 Uiso 0.50 1 calc PR B 2
H47 H 0.7913 0.7635 0.4177 0.150 Uiso 0.50 1 calc PR B 2
H48 H 0.6229 0.7089 0.3812 0.150 Uiso 0.50 1 calc PR B 2
C49 C 0.7003(18) 0.7084(12) 0.4799(8) 0.117(6) Uani 0.50 1 d P B 1
H49 H 0.6355 0.7513 0.4595 0.176 Uiso 0.50 1 calc PR B 1
H50 H 0.7994 0.7555 0.4951 0.176 Uiso 0.50 1 calc PR B 1
H51 H 0.6757 0.6846 0.5232 0.176 Uiso 0.50 1 calc PR B 1
C50 C 0.715(4) 0.625(4) 0.448(2) 0.109(10) Uani 0.50 1 d P B 2
H52 H 0.6975 0.6626 0.4931 0.131 Uiso 0.50 1 calc PR B 2
H53 H 0.8072 0.6050 0.4613 0.131 Uiso 0.50 1 calc PR B 2
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'
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
C2 C1 C3 119.7(6) . .
C1 C2 C4 120.6(6) . .
C1 C3 C5 120.0(6) . .
C2 C4 C6 120.8(5) . .
C6 C5 C3 120.6(5) . .
C4 C6 C5 118.3(5) . .
C4 C6 C7 119.7(5) . .
C5 C6 C7 122.0(5) . .
C8 C7 C6 128.0(4) . .
C8 C7 S1 109.3(4) . .
C6 C7 S1 122.5(3) . .
C7 C8 C9 114.8(5) . .
C10 C9 C8 113.7(5) . .
C9 C10 C11 130.9(4) . .
C9 C10 S1 109.2(4) . .
C11 C10 S1 119.9(3) . .
C12 C11 N1 107.2(4) . .
C12 C11 C10 129.6(4) . .
N1 C11 C10 123.1(4) . .
C11 C12 C13 108.2(4) . .
C14 C13 C12 108.4(4) . .
C13 C14 N1 107.6(4) . .
C13 C14 C21 130.0(4) . .
N1 C14 C21 122.4(4) . .
N1 C15 C16 111.2(4) . .
C17 C16 C15 114.3(5) . .
C16 C17 C18 114.1(5) . .
C19 C18 C17 114.8(6) . .
C18 C19 C20 114.0(6) . .
C22 C21 C14 129.4(4) . .
C22 C21 S2 110.0(4) . .
C14 C21 S2 120.6(3) . .
C21 C22 C23 113.5(4) . .
C24 C23 C22 113.9(4) . .
C23 C24 C24 128.6(5) . 2_756
C23 C24 S2 110.1(3) . .
C24 C24 S2 121.3(5) 2_756 .
C26 C25 C27 118.8(6) . .
C25 C26 C28 121.1(6) . .
C29 C27 C25 120.4(6) . .
C26 C28 C30 120.6(5) . .
C27 C29 C30 121.0(5) . .
C29 C30 C28 118.2(5) . .
C29 C30 C31 122.6(5) . .
C28 C30 C31 119.2(5) . .
C32 C31 C30 128.5(5) . .
C32 C31 S3 109.1(4) . .
C30 C31 S3 122.2(4) . .
C31 C32 C33 114.1(5) . .
C34 C33 C32 115.0(5) . .
C33 C34 C35 133.6(5) . .
C33 C34 S3 108.1(4) . .
C35 C34 S3 118.2(4) . .
N2 C35 C36 106.5(4) . .
N2 C35 C34 126.9(4) . .
C36 C35 C34 126.6(5) . .
C37 C36 C35 108.4(4) . .
C38 C37 C36 108.6(4) . .
C37 C38 N2 107.0(4) . .
C37 C38 C44 125.6(4) . .
N2 C38 C44 127.5(4) . .
N2 C39 C40 113.7(4) . .
C41 C40 C39 112.1(4) . .
C42 C41 C40 114.6(5) . .
C43 C42 C41 114(2) . .
C43 C42 C50 13(3) . .
C41 C42 C50 118.0(17) . .
C42 C43 C49 128(4) . .
C45 C44 C38 124.9(5) . .
C45 C44 S4 109.3(4) . .
C38 C44 S4 125.4(4) . .
C44 C45 C46 113.5(5) . .
C47 C46 C45 114.9(5) . .
C46 C47 C47 129.8(6) . 2_656
C46 C47 S4 109.4(4) . .
C47 C47 S4 120.8(5) 2_656 .
C14 N1 C11 108.6(4) . .
C14 N1 C15 122.2(4) . .
C11 N1 C15 124.9(4) . .
C38 N2 C35 109.6(4) . .
C38 N2 C39 125.6(4) . .
C35 N2 C39 124.4(4) . .
C10 S1 C7 93.0(2) . .
C21 S2 C24 92.5(2) . .
C34 S3 C31 93.6(2) . .
C47 S4 C44 92.9(2) . .
C48 C50 C42 104(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.367(7) .
C1 C3 1.369(7) .
C2 C4 1.373(7) .
C3 C5 1.388(7) .
C4 C6 1.381(7) .
C5 C6 1.384(6) .
C6 C7 1.468(6) .
C7 C8 1.344(6) .
C7 S1 1.733(5) .
C8 C9 1.396(6) .
C9 C10 1.368(6) .
C10 C11 1.449(6) .
C10 S1 1.727(4) .
C11 C12 1.379(6) .
C11 N1 1.391(5) .
C12 C13 1.394(6) .
C13 C14 1.371(6) .
C14 N1 1.386(5) .
C14 C21 1.453(6) .
C15 N1 1.469(5) .
C15 C16 1.525(7) .
C16 C17 1.470(7) .
C17 C18 1.528(8) .
C18 C19 1.470(7) .
C19 C20 1.492(8) .
C21 C22 1.356(6) .
C21 S2 1.721(5) .
C22 C23 1.403(6) .
C23 C24 1.347(6) .
C24 C24 1.456(9) 2_756
C24 S2 1.724(4) .
C25 C26 1.367(7) .
C25 C27 1.384(7) .
C26 C28 1.370(7) .
C27 C29 1.375(7) .
C28 C30 1.391(6) .
C29 C30 1.376(6) .
C30 C31 1.471(6) .
C31 C32 1.355(6) .
C31 S3 1.736(5) .
C32 C33 1.398(7) .
C33 C34 1.371(6) .
C34 C35 1.439(6) .
C34 S3 1.733(5) .
C35 N2 1.385(5) .
C35 C36 1.389(6) .
C36 C37 1.383(6) .
C37 C38 1.378(6) .
C38 N2 1.382(5) .
C38 C44 1.452(6) .
C39 N2 1.468(5) .
C39 C40 1.528(6) .
C40 C41 1.516(6) .
C41 C42 1.495(7) .
C42 C43 1.38(4) .
C42 C50 1.66(4) .
C43 C49 1.41(4) .
C44 C45 1.357(6) .
C44 S4 1.736(5) .
C45 C46 1.400(7) .
C46 C47 1.345(6) .
C47 C47 1.459(9) 2_656
C47 S4 1.725(5) .
C48 C50 1.38(4) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168340356
