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#$Date: 2025-08-18 23:06:14 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301780 $
#$URL: svn://www.crystallography.net/cod/cif/1/55/94/1559499.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_1559499
loop_
_publ_author_name
'Sui, Ying'
'Shi, Yibo'
'Deng, Yunfeng'
'Li, Riqing'
'Bai, Junhua'
'Wang, Zhongli'
'Dang, Yanfeng'
'Han, Yang'
'Kirby, Nigel'
'Ye, Long'
'Geng, Yanhou'
_publ_section_title
;
 Direct Arylation Polycondensation of Chlorinated Thiophene Derivatives to
 High-Mobility Conjugated Polymers
;
_journal_issue                   22
_journal_name_full               Macromolecules
_journal_page_first              10147
_journal_page_last               10154
_journal_paper_doi               10.1021/acs.macromol.0c02206
_journal_volume                  53
_journal_year                    2020
_chemical_formula_moiety         'C10 H4 Cl4 S2'
_chemical_formula_sum            'C10 H4 Cl4 S2'
_chemical_formula_weight         330.05
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-11-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.219(13)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.5288(16)
_cell_length_b                   9.877(3)
_cell_length_c                   13.772(4)
_cell_measurement_reflns_used    3074
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.74
_cell_measurement_theta_min      4.80
_cell_volume                     613.5(3)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.15
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7590
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.964
_diffrn_reflns_theta_min         4.800
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    7.631
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5305
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1886 before and 0.0631 after correction. The Ratio of minimum to maximum transmission is 0.7066. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.787
_exptl_crystal_description       needle
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.005
_refine_diff_density_max         0.726
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     73
_refine_ls_number_reflns         1160
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.140
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0397
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0564P)²+1.0128P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1023
_refine_ls_wR_factor_ref         0.1184
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1075
_reflns_number_total             1160
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ma0c02206_si_003.cif
_cod_data_source_block           191106dyf_0m_pl
_cod_depositor_comments
'Adding full bibliography for 1559498--1559499.cif.'
_cod_database_code               1559499
_shelx_shelxl_version_number     2016/6
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.6494(2) 0.35787(9) 0.22546(6) 0.0431(3) Uani 1 1 d . . . . .
Cl2 Cl 0.2241(2) 0.09779(8) 0.15702(6) 0.0405(3) Uani 1 1 d . . . . .
S1 S 0.6146(2) 0.28084(8) -0.07684(6) 0.0347(3) Uani 1 1 d . . . . .
C1 C 0.9376(7) 0.4728(3) 0.0374(2) 0.0302(7) Uani 1 1 d . . . . .
H1 H 0.990162 0.510715 0.100011 0.036 Uiso 1 1 calc R . . . .
C2 C 0.7300(7) 0.3618(3) 0.0321(2) 0.0307(7) Uani 1 1 d . . . . .
C3 C 0.5976(8) 0.3029(3) 0.1071(2) 0.0320(7) Uani 1 1 d . . . . .
C4 C 0.4105(7) 0.1931(3) 0.0776(2) 0.0312(7) Uani 1 1 d . . . . .
C5 C 0.3975(8) 0.1694(3) -0.0203(2) 0.0347(7) Uani 1 1 d . . . . .
H5 H 0.282402 0.099821 -0.052869 0.042 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 0.0148 0.0070 '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'
Cl Cl 0.3294 0.5404 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2924 0.4247 '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
_geom_angle_publ_flag
C5 S1 C2 92.48(16) . . ?
C1 C1 H1 117.0 3_765 . ?
C1 C1 C2 126.0(4) 3_765 . ?
C2 C1 H1 117.0 . . ?
C1 C2 S1 122.5(2) . . ?
C3 C2 S1 109.7(3) . . ?
C3 C2 C1 127.7(3) . . ?
C2 C3 Cl1 123.4(3) . . ?
C2 C3 C4 113.7(3) . . ?
C4 C3 Cl1 122.9(3) . . ?
C3 C4 Cl2 123.6(3) . . ?
C5 C4 Cl2 123.7(3) . . ?
C5 C4 C3 112.7(3) . . ?
S1 C5 H5 124.3 . . ?
C4 C5 S1 111.4(3) . . ?
C4 C5 H5 124.3 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C3 1.714(3) . ?
Cl2 C4 1.721(3) . ?
S1 C2 1.737(3) . ?
S1 C5 1.710(4) . ?
C1 C1 1.333(7) 3_765 ?
C1 H1 0.9500 . ?
C1 C2 1.442(5) . ?
C2 C3 1.370(5) . ?
C3 C4 1.413(5) . ?
C4 C5 1.364(5) . ?
C5 H5 0.9500 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C3 C4 Cl2 -2.5(4) . . . . ?
Cl1 C3 C4 C5 178.5(2) . . . . ?
Cl2 C4 C5 S1 -178.81(19) . . . . ?
S1 C2 C3 Cl1 -178.28(19) . . . . ?
S1 C2 C3 C4 1.0(4) . . . . ?
C1 C1 C2 S1 0.6(6) 3_765 . . . ?
C1 C1 C2 C3 179.8(4) 3_765 . . . ?
C1 C2 C3 Cl1 2.4(5) . . . . ?
C1 C2 C3 C4 -178.3(3) . . . . ?
C2 S1 C5 C4 0.3(3) . . . . ?
C2 C3 C4 Cl2 178.2(2) . . . . ?
C2 C3 C4 C5 -0.8(4) . . . . ?
C3 C4 C5 S1 0.2(4) . . . . ?
C5 S1 C2 C1 178.6(3) . . . . ?
C5 S1 C2 C3 -0.8(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 155662733
