#------------------------------------------------------------------------------
#$Date: 2019-11-28 21:22:44 +0200 (Thu, 28 Nov 2019) $
#$Revision: 244660 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/93/7239335.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_7239335
loop_
_publ_author_name
'Tusy, Chuong'
'Huang, Lili'
'Jin, Jingpeng'
'Xia, Jiangbin'
_publ_section_title
;
 Synthesis and investigation of novel thiophene derivatives containing
 heteroatom linkers for solid state polymerization
;
_journal_issue                   16
_journal_name_full               'RSC Advances'
_journal_page_first              8011
_journal_paper_doi               10.1039/c3ra45014g
_journal_volume                  4
_journal_year                    2014
_chemical_formula_sum            'C13 H10 Br2 O4 S2'
_chemical_formula_weight         454.15
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 110.803(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.665(3)
_cell_length_b                   8.8588(19)
_cell_length_c                   14.424(3)
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.5
_cell_measurement_theta_min      2.45
_cell_volume                     1512.8(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0416
_diffrn_reflns_av_sigmaI/netI    0.0489
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9083
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         1.72
_exptl_absorpt_coefficient_mu    5.645
_exptl_absorpt_correction_T_max  0.3981
_exptl_absorpt_correction_T_min  0.2653
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_density_diffrn    1.994
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.259
_refine_diff_density_min         -0.486
_refine_diff_density_rms         0.203
_refine_ls_extinction_coef       0.0100(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3134
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.1002
_refine_ls_R_factor_gt           0.0643
_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)+(0.1085P)²+2.6536P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1745
_refine_ls_wR_factor_ref         0.2005
_reflns_number_gt                2056
_reflns_number_total             3134
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ra45014g.txt
_cod_data_source_block           130311xjb2_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        1512.8(5)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7239335
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br -0.42277(8) 0.27244(13) 0.13954(8) 0.0840(4) Uani 1 1 d .
Br2 Br 0.23911(7) 0.55616(11) 0.03750(6) 0.0731(4) Uani 1 1 d .
C1 C -0.2764(6) 0.2169(9) 0.1514(6) 0.0558(18) Uani 1 1 d .
C2 C -0.2472(5) 0.1229(7) 0.0948(4) 0.0393(14) Uani 1 1 d .
C3 C -0.1273(6) 0.1040(8) 0.1277(5) 0.0450(15) Uani 1 1 d .
C4 C -0.0698(6) 0.1824(8) 0.2086(5) 0.0466(16) Uani 1 1 d .
C5 C -0.2740(7) -0.0700(8) -0.0400(8) 0.068(2) Uani 1 1 d .
H5A H -0.2793 -0.1701 -0.0147 0.082 Uiso 1 1 calc R
H5B H -0.3150 -0.0685 -0.1110 0.082 Uiso 1 1 calc R
C6 C -0.1526(9) -0.0240(12) -0.0157(7) 0.083(3) Uani 1 1 d .
H6A H -0.1171 -0.1056 -0.0387 0.100 Uiso 1 1 calc R
H6B H -0.1540 0.0622 -0.0576 0.100 Uiso 1 1 calc R
C7 C 0.0526(6) 0.1866(9) 0.2688(5) 0.0529(17) Uani 1 1 d .
H7A H 0.0795 0.0835 0.2816 0.063 Uiso 1 1 calc R
H7B H 0.0616 0.2323 0.3323 0.063 Uiso 1 1 calc R
C8 C 0.1268(5) 0.2696(7) 0.2252(5) 0.0424(15) Uani 1 1 d .
C9 C 0.2414(5) 0.2700(7) 0.2617(5) 0.0419(14) Uani 1 1 d .
C10 C 0.2910(5) 0.3647(8) 0.2081(5) 0.0434(15) Uani 1 1 d .
C11 C 0.2115(6) 0.4289(8) 0.1296(5) 0.0463(16) Uani 1 1 d .
C12 C 0.4640(7) 0.3292(13) 0.3291(7) 0.087(3) Uani 1 1 d D
H12A H 0.5429 0.3176 0.3370 0.104 Uiso 1 1 calc R
H12B H 0.4595 0.4050 0.3761 0.104 Uiso 1 1 calc R
C13 C 0.4237(7) 0.1917(12) 0.3515(9) 0.101(4) Uani 1 1 d D
H13A H 0.4699 0.1632 0.4186 0.122 Uiso 1 1 calc R
H13B H 0.4336 0.1149 0.3073 0.122 Uiso 1 1 calc R
O1 O -0.3194(4) 0.0507(6) 0.0130(4) 0.0638(14) Uani 1 1 d .
O2 O -0.0748(4) 0.0152(5) 0.0832(3) 0.0466(11) Uani 1 1 d .
O3 O 0.4037(4) 0.3799(7) 0.2326(4) 0.0603(14) Uani 1 1 d .
O4 O 0.3037(4) 0.1913(6) 0.3435(4) 0.0600(13) Uani 1 1 d .
S1 S -0.16388(17) 0.2858(2) 0.24786(15) 0.0570(5) Uani 1 1 d .
S2 S 0.07656(14) 0.3828(2) 0.12180(13) 0.0472(5) Uani 1 1 d .
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'
O O 0.0106 0.0060 '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'
Br Br -0.2901 2.4595 '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
C2 C1 S1 113.3(6)
C2 C1 Br1 127.0(6)
S1 C1 Br1 119.6(4)
C1 C2 O1 125.8(6)
C1 C2 C3 111.7(6)
O1 C2 C3 122.5(6)
C4 C3 O2 121.3(6)
C4 C3 C2 114.6(6)
O2 C3 C2 124.2(6)
C3 C4 C7 131.2(7)
C3 C4 S1 109.5(5)
C7 C4 S1 119.2(5)
C6 C5 O1 103.1(6)
C6 C5 H5A 111.1
O1 C5 H5A 111.1
C6 C5 H5B 111.1
O1 C5 H5B 111.1
H5A C5 H5B 109.1
O2 C6 C5 124.8(8)
O2 C6 H6A 106.1
C5 C6 H6A 106.1
O2 C6 H6B 106.1
C5 C6 H6B 106.1
H6A C6 H6B 106.3
C4 C7 C8 116.6(6)
C4 C7 H7A 108.1
C8 C7 H7A 108.1
C4 C7 H7B 108.1
C8 C7 H7B 108.1
H7A C7 H7B 107.3
C9 C8 C7 125.7(6)
C9 C8 S2 110.5(5)
C7 C8 S2 123.8(5)
O4 C9 C8 123.2(6)
O4 C9 C10 122.8(6)
C8 C9 C10 114.0(6)
C11 C10 O3 125.8(6)
C11 C10 C9 111.2(6)
O3 C10 C9 122.9(6)
C10 C11 S2 112.6(5)
C10 C11 Br2 125.4(5)
S2 C11 Br2 122.0(4)
C13 C12 O3 113.1(8)
C13 C12 H12A 109.0
O3 C12 H12A 109.0
C13 C12 H12B 109.0
O3 C12 H12B 109.0
H12A C12 H12B 107.8
C12 C13 O4 115.5(8)
C12 C13 H13A 108.4
O4 C13 H13A 108.4
C12 C13 H13B 108.4
O4 C13 H13B 108.4
H13A C13 H13B 107.5
C2 O1 C5 120.0(6)
C3 O2 C6 109.4(5)
C10 O3 C12 112.4(6)
C9 O4 C13 109.2(6)
C1 S1 C4 90.9(3)
C8 S2 C11 91.6(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C1 1.866(8)
Br2 C11 1.868(6)
C1 C2 1.309(10)
C1 S1 1.712(8)
C2 O1 1.368(8)
C2 C3 1.431(9)
C3 C4 1.331(10)
C3 O2 1.333(8)
C4 C7 1.484(9)
C4 S1 1.749(7)
C5 C6 1.507(13)
C5 O1 1.540(9)
C5 H5A 0.9700
C5 H5B 0.9700
C6 O2 1.459(10)
C6 H6A 0.9700
C6 H6B 0.9700
C7 C8 1.496(9)
C7 H7A 0.9700
C7 H7B 0.9700
C8 C9 1.357(9)
C8 S2 1.721(7)
C9 O4 1.356(8)
C9 C10 1.429(9)
C10 C11 1.345(9)
C10 O3 1.349(8)
C11 S2 1.721(7)
C12 C13 1.402(9)
C12 O3 1.403(10)
C12 H12A 0.9700
C12 H12B 0.9700
C13 O4 1.483(11)
C13 H13A 0.9700
C13 H13B 0.9700
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
S1 C1 C2 O1 179.7(5)
Br1 C1 C2 O1 2.4(11)
S1 C1 C2 C3 -0.9(8)
Br1 C1 C2 C3 -178.2(5)
C1 C2 C3 C4 0.8(9)
O1 C2 C3 C4 -179.9(6)
C1 C2 C3 O2 -179.6(6)
O1 C2 C3 O2 -0.3(10)
O2 C3 C4 C7 -3.9(12)
C2 C3 C4 C7 175.7(7)
O2 C3 C4 S1 -179.8(5)
C2 C3 C4 S1 -0.2(7)
O1 C5 C6 O2 47.7(11)
C3 C4 C7 C8 74.7(10)
S1 C4 C7 C8 -109.7(7)
C4 C7 C8 C9 -170.9(7)
C4 C7 C8 S2 10.9(10)
C7 C8 C9 O4 1.0(11)
S2 C8 C9 O4 179.5(5)
C7 C8 C9 C10 -177.1(6)
S2 C8 C9 C10 1.3(7)
O4 C9 C10 C11 179.4(6)
C8 C9 C10 C11 -2.4(8)
O4 C9 C10 O3 2.1(10)
C8 C9 C10 O3 -179.7(6)
O3 C10 C11 S2 179.6(5)
C9 C10 C11 S2 2.4(8)
O3 C10 C11 Br2 -0.9(10)
C9 C10 C11 Br2 -178.1(5)
O3 C12 C13 O4 -59.0(14)
C1 C2 O1 C5 -173.4(7)
C3 C2 O1 C5 7.4(10)
C6 C5 O1 C2 -26.5(10)
C4 C3 O2 C6 -165.0(7)
C2 C3 O2 C6 15.5(9)
C5 C6 O2 C3 -43.6(11)
C11 C10 O3 C12 166.3(8)
C9 C10 O3 C12 -16.8(10)
C13 C12 O3 C10 43.9(12)
C8 C9 O4 C13 168.9(8)
C10 C9 O4 C13 -13.1(10)
C12 C13 O4 C9 41.1(12)
C2 C1 S1 C4 0.7(6)
Br1 C1 S1 C4 178.2(5)
C3 C4 S1 C1 -0.3(6)
C7 C4 S1 C1 -176.8(6)
C9 C8 S2 C11 0.0(5)
C7 C8 S2 C11 178.5(6)
C10 C11 S2 C8 -1.4(6)
Br2 C11 S2 C8 179.0(4)
