#------------------------------------------------------------------------------
#$Date: 2025-08-18 17:20:24 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301776 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/51/30/1513095.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_1513095
loop_
_publ_author_name
'Schneider, Julia A.'
'Dadvand, Afshin'
'Wen, Wen'
'Perepichka, Dmitrii F.'
_publ_section_title
;
 Tuning the Electronic Properties of Poly(thienothiophene vinylene)s via
 Alkylsulfanyl and Alkylsulfonyl Substituents
;
_journal_issue                   23
_journal_name_full               Macromolecules
_journal_page_first              9231
_journal_paper_doi               10.1021/ma402018n
_journal_volume                  46
_journal_year                    2013
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety         'C30 H40 S8'
_chemical_formula_sum            'C30 H40 S8'
_chemical_formula_weight         657.10
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_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-2013
_cell_angle_alpha                99.111(2)
_cell_angle_beta                 105.013(2)
_cell_angle_gamma                101.559(2)
_cell_formula_units_Z            1
_cell_length_a                   6.6801(3)
_cell_length_b                   11.5170(4)
_cell_length_c                   11.5244(5)
_cell_measurement_reflns_used    9888
_cell_measurement_temperature    100
_cell_measurement_theta_max      70.12
_cell_measurement_theta_min      4.02
_cell_volume                     818.02(6)
_computing_cell_refinement       'SAINT V8.30C(Bruker AXS, 2013)'
_computing_data_collection       'APEX2  (Bruker AXS, 2013)'
_computing_data_reduction        'SAINT V8.30C(Bruker AXS, 2013)'
_computing_molecular_graphics    'XP  (Bruker AXS, 1998)'
_computing_publication_material  'UdMX (Maris, 2004)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker Microstar'
_diffrn_measurement_method       ω
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.057
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            23678
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.212
_diffrn_reflns_theta_min         4.018
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    5.193
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.4625
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 2012)'
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_description       Fragment
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.577
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         3061
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0436
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0822P)²+0.2760P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1191
_refine_ls_wR_factor_ref         0.1245
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2735
_reflns_number_total             3061
_cod_data_source_file            ma402018n_si_002.cif
_cod_data_source_block           PERE39
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1513095
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.423
_shelx_estimated_absorpt_t_max   0.819
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
S1 S 0.45110(8) 0.56576(4) 0.64386(4) 0.02872(17) Uani 1 1 d . .
S2 S 0.66726(8) 0.26666(5) 0.73041(5) 0.03548(18) Uani 1 1 d . .
S3 S 0.10344(8) 0.18831(4) 0.56318(5) 0.03648(18) Uani 1 1 d . .
S4 S 1.00993(8) 0.64477(5) 0.82258(5) 0.03577(18) Uani 1 1 d . .
C1 C 0.2311(3) 0.43921(18) 0.58262(18) 0.0288(4) Uani 1 1 d . .
C2 C 0.2840(3) 0.33326(18) 0.60692(19) 0.0307(4) Uani 1 1 d . .
C3 C 0.5042(3) 0.35696(18) 0.67444(18) 0.0312(4) Uani 1 1 d . .
C4 C 0.8829(3) 0.39263(19) 0.7932(2) 0.0354(5) Uani 1 1 d . .
H4 H 1.0213 0.3881 0.8376 0.042 Uiso 1 1 calc R U
C5 C 0.8361(3) 0.49931(19) 0.77293(18) 0.0305(4) Uani 1 1 d . .
C6 C 0.6159(3) 0.47741(18) 0.70317(18) 0.0290(4) Uani 1 1 d . .
C7 C 0.0230(3) 0.44928(17) 0.51543(18) 0.0295(4) Uani 1 1 d . .
H7 H -0.0915 0.3779 0.4909 0.035 Uiso 1 1 calc R U
C8 C 0.1182(3) 0.13640(18) 0.4085(2) 0.0371(5) Uani 1 1 d . .
H8A H 0.0063 0.0596 0.3687 0.044 Uiso 1 1 calc R U
H8B H 0.0848 0.1974 0.3599 0.044 Uiso 1 1 calc R U
C9 C 0.3325(3) 0.11521(18) 0.4028(2) 0.0368(5) Uani 1 1 d . .
H9A H 0.4463 0.1908 0.4447 0.044 Uiso 1 1 calc R U
H9B H 0.3638 0.0511 0.4474 0.044 Uiso 1 1 calc R U
C10 C 0.3354(3) 0.07746(19) 0.2714(2) 0.0398(5) Uani 1 1 d . .
H10A H 0.2959 0.1395 0.2257 0.048 Uiso 1 1 calc R U
H10B H 0.2265 -0.0004 0.2310 0.048 Uiso 1 1 calc R U
C11 C 0.5534(4) 0.0624(2) 0.2641(2) 0.0466(6) Uani 1 1 d . .
H11A H 0.5460 0.0356 0.1777 0.070 Uiso 1 1 calc R U
H11B H 0.5939 0.0016 0.3098 0.070 Uiso 1 1 calc R U
H11C H 0.6605 0.1403 0.3000 0.070 Uiso 1 1 calc R U
C12 C 1.2506(3) 0.61402(19) 0.91199(19) 0.0349(5) Uani 1 1 d . .
H12A H 1.2229 0.5805 0.9819 0.042 Uiso 1 1 calc R U
H12B H 1.2946 0.5530 0.8600 0.042 Uiso 1 1 calc R U
C13 C 1.4291(3) 0.73080(19) 0.96036(19) 0.0374(5) Uani 1 1 d . .
H13A H 1.4494 0.7663 0.8901 0.045 Uiso 1 1 calc R U
H13B H 1.3860 0.7900 1.0149 0.045 Uiso 1 1 calc R U
C14 C 1.6392(4) 0.7103(2) 1.0310(2) 0.0390(5) Uani 1 1 d . .
H14A H 1.6839 0.6524 0.9761 0.047 Uiso 1 1 calc R U
H14B H 1.6185 0.6736 1.1005 0.047 Uiso 1 1 calc R U
C15 C 1.8156(4) 0.8282(2) 1.0810(2) 0.0501(6) Uani 1 1 d . .
H15A H 1.8285 0.8683 1.0133 0.075 Uiso 1 1 calc R U
H15B H 1.9518 0.8100 1.1186 0.075 Uiso 1 1 calc R U
H15C H 1.7800 0.8820 1.1431 0.075 Uiso 1 1 calc R U
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
S S 0.3331 0.5567 '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_site_symmetry_1
_geom_angle
_geom_angle_publ_flag
C6 S1 C1 . 91.71(9) y
C3 S2 C4 . 90.70(10) y
C2 S3 C8 . 100.83(10) y
C5 S4 C12 . 101.27(10) y
C2 C1 C7 . 126.18(19) y
C2 C1 S1 . 111.91(16) y
C7 C1 S1 . 121.92(15) y
C1 C2 C3 . 110.96(19) y
C1 C2 S3 . 125.06(16) y
C3 C2 S3 . 123.98(15) y
C6 C3 C2 . 114.79(18) y
C6 C3 S2 . 111.37(16) y
C2 C3 S2 . 133.84(16) y
C5 C4 S2 . 113.91(16) y
C5 C4 H4 . 123.0 ?
S2 C4 H4 . 123.0 ?
C4 C5 C6 . 110.24(19) y
C4 C5 S4 . 127.31(17) y
C6 C5 S4 . 122.45(16) y
C3 C6 C5 . 113.77(18) y
C3 C6 S1 . 110.63(16) y
C5 C6 S1 . 135.60(16) y
C7 C7 C1 2_566 125.7(2) y
C7 C7 H7 2_566 117.2 ?
C1 C7 H7 . 117.2 ?
C9 C8 S3 . 114.99(16) y
C9 C8 H8A . 108.5 ?
S3 C8 H8A . 108.5 ?
C9 C8 H8B . 108.5 ?
S3 C8 H8B . 108.5 ?
H8A C8 H8B . 107.5 ?
C10 C9 C8 . 111.94(18) y
C10 C9 H9A . 109.2 ?
C8 C9 H9A . 109.2 ?
C10 C9 H9B . 109.2 ?
C8 C9 H9B . 109.2 ?
H9A C9 H9B . 107.9 ?
C9 C10 C11 . 112.52(18) y
C9 C10 H10A . 109.1 ?
C11 C10 H10A . 109.1 ?
C9 C10 H10B . 109.1 ?
C11 C10 H10B . 109.1 ?
H10A C10 H10B . 107.8 ?
C10 C11 H11A . 109.5 ?
C10 C11 H11B . 109.5 ?
H11A C11 H11B . 109.5 ?
C10 C11 H11C . 109.5 ?
H11A C11 H11C . 109.5 ?
H11B C11 H11C . 109.5 ?
C13 C12 S4 . 109.73(14) y
C13 C12 H12A . 109.7 ?
S4 C12 H12A . 109.7 ?
C13 C12 H12B . 109.7 ?
S4 C12 H12B . 109.7 ?
H12A C12 H12B . 108.2 ?
C14 C13 C12 . 112.50(17) y
C14 C13 H13A . 109.1 ?
C12 C13 H13A . 109.1 ?
C14 C13 H13B . 109.1 ?
C12 C13 H13B . 109.1 ?
H13A C13 H13B . 107.8 ?
C13 C14 C15 . 112.06(18) y
C13 C14 H14A . 109.2 ?
C15 C14 H14A . 109.2 ?
C13 C14 H14B . 109.2 ?
C15 C14 H14B . 109.2 ?
H14A C14 H14B . 107.9 ?
C14 C15 H15A . 109.5 ?
C14 C15 H15B . 109.5 ?
H15A C15 H15B . 109.5 ?
C14 C15 H15C . 109.5 ?
H15A C15 H15C . 109.5 ?
H15B C15 H15C . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C6 . 1.7303(19) y
S1 C1 . 1.749(2) y
S2 C3 . 1.7281(19) y
S2 C4 . 1.730(2) y
S3 C2 . 1.763(2) y
S3 C8 . 1.823(2) y
S4 C5 . 1.748(2) y
S4 C12 . 1.805(2) y
C1 C2 . 1.386(3) y
C1 C7 . 1.442(3) y
C2 C3 . 1.422(3) y
C3 C6 . 1.379(3) y
C4 C5 . 1.367(3) y
C4 H4 . 0.9500 ?
C5 C6 . 1.431(3) y
C7 C7 2_566 1.343(4) y
C7 H7 . 0.9500 ?
C8 C9 . 1.515(3) y
C8 H8a . 0.9900 ?
C8 H8b . 0.9900 ?
C9 C10 . 1.515(3) y
C9 H9a . 0.9900 ?
C9 H9b . 0.9900 ?
C10 C11 . 1.522(3) y
C10 H10a . 0.9900 ?
C10 H10b . 0.9900 ?
C11 H11a . 0.9800 ?
C11 H11b . 0.9800 ?
C11 H11c . 0.9800 ?
C12 C13 . 1.522(3) y
C12 H12a . 0.9900 ?
C12 H12b . 0.9900 ?
C13 C14 . 1.513(3) y
C13 H13a . 0.9900 ?
C13 H13b . 0.9900 ?
C14 C15 . 1.524(3) y
C14 H14a . 0.9900 ?
C14 H14b . 0.9900 ?
C15 H15a . 0.9800 ?
C15 H15b . 0.9800 ?
C15 H15c . 0.9800 ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 S1 C1 C2 . -0.20(16) y
C6 S1 C1 C7 . 179.87(17) y
C7 C1 C2 C3 . 179.44(18) y
S1 C1 C2 C3 . -0.5(2) y
C7 C1 C2 S3 . -1.6(3) y
S1 C1 C2 S3 . 178.44(11) y
C8 S3 C2 C1 . 87.1(2) y
C8 S3 C2 C3 . -94.13(18) y
C1 C2 C3 C6 . 1.2(3) y
S3 C2 C3 C6 . -177.76(15) y
C1 C2 C3 S2 . -179.08(17) y
S3 C2 C3 S2 . 2.0(3) y
C4 S2 C3 C6 . 0.61(17) y
C4 S2 C3 C2 . -179.1(2) y
C3 S2 C4 C5 . -0.23(18) y
S2 C4 C5 C6 . -0.2(2) y
S2 C4 C5 S4 . 179.44(12) y
C12 S4 C5 C4 . -3.4(2) y
C12 S4 C5 C6 . 176.16(17) y
C2 C3 C6 C5 . 178.96(16) y
S2 C3 C6 C5 . -0.8(2) y
C2 C3 C6 S1 . -1.3(2) y
S2 C3 C6 S1 . 178.88(9) y
C4 C5 C6 C3 . 0.7(3) y
S4 C5 C6 C3 . -178.98(16) y
C4 C5 C6 S1 . -178.96(18) y
S4 C5 C6 S1 . 1.4(3) y
C1 S1 C6 C3 . 0.85(17) y
C1 S1 C6 C5 . -179.5(2) y
C2 C1 C7 C7 2_566 -174.8(2) y
S1 C1 C7 C7 2_566 5.1(4) y
C2 S3 C8 C9 . 66.50(17) y
S3 C8 C9 C10 . -177.58(14) y
C8 C9 C10 C11 . 176.94(18) y
C5 S4 C12 C13 . 177.65(14) y
S4 C12 C13 C14 . -177.14(15) y
C12 C13 C14 C15 . -178.99(19) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139041647
