#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/19/7051967.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_7051967
loop_
_publ_author_name
'Hergué, Noémie'
'Leriche, Philippe'
'Blanchard, Philippe'
'Allain, Magali'
'Gallego-Planas, Nuria'
'Frère, Pierre'
'Roncali, Jean'
_publ_section_title
;
 Evidence for the contribution of sulfur--bromine intramolecular
 interactions to the self-rigidification of thiophene-based
 π-conjugated systems
;
_journal_issue                   6
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              932
_journal_paper_doi               10.1039/b802313a
_journal_volume                  32
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C10 H7 Br1 O2 S2'
_chemical_formula_sum            'C10 H7 Br O2 S2'
_chemical_formula_weight         303.19
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_audit_creation_date             2008-03-10T16:24:06-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.1115(4)
_cell_length_b                   14.688(1)
_cell_length_c                   17.247(2)
_cell_measurement_reflns_used    5571
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.95
_cell_measurement_theta_min      2.4
_cell_volume                     1041.54(17)
_computing_cell_refinement       'SELECT,CELL, STOE IPDS'
_computing_data_collection       'EXPOSE, STOE IPDS'
_computing_data_reduction        'INTEGRATE, STOE IPDS'
_computing_molecular_graphics    'DIAMOND 3.1 (Crystal Impact GbR 2005)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'Direct methods (Sir92,Altomare et al.,1993)'
_diffrn_detector_area_resol_mean 6.66
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'STOE IPDS'
_diffrn_measurement_method       'Oscillation Phi Incr 1.3 deg'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6104
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         2.36
_exptl_absorpt_coefficient_mu    4.32
_exptl_absorpt_correction_T_max  0.5689
_exptl_absorpt_correction_T_min  0.3902
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
PLATON-ABSGAUSS : Spek, A.L. (2003), J.Appl.Cryst. 36, 7-13
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.933
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.77
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.415
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.020(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         1988
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.978
_refine_ls_R_factor_gt           0.0292
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0474P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0721
_reflns_number_gt                1737
_reflns_number_total             1988
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b802313a.txt
_cod_data_source_block           nh933
_cod_database_code               7051967
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
_atom_site_disorder_assembly
C1 C 0.9197(12) 0.6080(3) 0.5529(2) 0.0500(9) Uani 1 d D . .
C2 C 0.8769(12) 0.5183(3) 0.5616(2) 0.0471(9) Uani 1 d . . .
C3 C 0.7053(9) 0.4801(2) 0.4982(2) 0.0422(7) Uani 1 d . . .
C4 C 0.6144(10) 0.5413(2) 0.44178(18) 0.0360(7) Uani 1 d . . .
C5 C 0.4402(9) 0.5298(2) 0.36949(19) 0.0355(8) Uani 1 d . . .
C6 C 0.3621(10) 0.5957(2) 0.31663(19) 0.0372(7) Uani 1 d . . .
C7 C 0.1913(10) 0.5631(3) 0.2507(2) 0.0425(9) Uani 1 d . . .
C8 C 0.1387(12) 0.4724(3) 0.2528(2) 0.0475(9) Uani 1 d D . .
C9 C 0.2544(14) 0.7434(3) 0.2735(2) 0.0468(9) Uani 1 d . . .
C10 C 0.2513(15) 0.7057(3) 0.1934(2) 0.0534(10) Uani 1 d . . .
O1 O 0.4441(7) 0.68536(16) 0.32530(15) 0.0451(6) Uani 1 d . . .
O2 O 0.0905(8) 0.61903(19) 0.19176(15) 0.0524(7) Uani 1 d . . .
S1 S 0.7545(3) 0.64903(6) 0.46874(5) 0.0442(2) Uani 1 d . . .
S2 S 0.2906(3) 0.42548(6) 0.33673(6) 0.0457(2) Uani 1 d . . .
Br Br 0.61021(11) 0.35458(2) 0.49612(2) 0.05363(14) Uani 1 d . . .
H1 H 1.037(11) 0.648(3) 0.583(2) 0.074(15) Uiso 1 d D . .
H2 H 0.970(10) 0.480(3) 0.603(2) 0.041(11) Uiso 1 d . . .
H8 H 0.031(12) 0.437(3) 0.215(2) 0.084(18) Uiso 1 d D . .
H9A H 0.376(11) 0.799(3) 0.273(2) 0.044(11) Uiso 1 d . . .
H9B H 0.045(13) 0.746(3) 0.295(3) 0.050(13) Uiso 1 d . . .
H10A H 0.445(12) 0.690(3) 0.179(3) 0.052(14) Uiso 1 d . . .
H10B H 0.113(13) 0.747(3) 0.156(3) 0.068(15) Uiso 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 S1 113.0(3) . . ?
C2 C1 H1 130(3) . . ?
S1 C1 H1 117(3) . . ?
C1 C2 C3 111.6(4) . . ?
C1 C2 H2 126(2) . . ?
C3 C2 H2 122(2) . . ?
C4 C3 C2 115.0(3) . . ?
C4 C3 Br 124.7(3) . . ?
C2 C3 Br 120.3(3) . . ?
C3 C4 C5 131.8(3) . . ?
C3 C4 S1 108.3(3) . . ?
C5 C4 S1 119.9(2) . . ?
C6 C5 C4 127.4(3) . . ?
C6 C5 S2 108.8(3) . . ?
C4 C5 S2 123.8(3) . . ?
C5 C6 O1 123.4(3) . . ?
C5 C6 C7 114.3(3) . . ?
O1 C6 C7 122.3(3) . . ?
C8 C7 O2 124.3(4) . . ?
C8 C7 C6 113.0(3) . . ?
O2 C7 C6 122.8(3) . . ?
C7 C8 S2 111.1(3) . . ?
C7 C8 H8 127(4) . . ?
S2 C8 H8 122(4) . . ?
O1 C9 C10 110.7(4) . . ?
O1 C9 H9A 103(3) . . ?
C10 C9 H9A 108(2) . . ?
O1 C9 H9B 106(3) . . ?
C10 C9 H9B 112(3) . . ?
H9A C9 H9B 117(4) . . ?
O2 C10 C9 110.7(3) . . ?
O2 C10 H10A 100(3) . . ?
C9 C10 H10A 111(3) . . ?
O2 C10 H10B 104(3) . . ?
C9 C10 H10B 111(3) . . ?
H10A C10 H10B 118(4) . . ?
C6 O1 C9 111.3(3) . . ?
C7 O2 C10 112.2(3) . . ?
C1 S1 C4 92.15(19) . . ?
C8 S2 C5 92.80(19) . . ?
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
C1 C2 1.338(6) . ?
C1 S1 1.712(4) . ?
C1 H1 0.921(19) . ?
C2 C3 1.417(6) . ?
C2 H2 0.99(4) . ?
C3 C4 1.377(5) . ?
C3 Br 1.885(3) . ?
C4 C5 1.448(5) . ?
C4 S1 1.746(4) . ?
C5 C6 1.368(5) . ?
C5 S2 1.745(3) . ?
C6 O1 1.368(4) . ?
C6 C7 1.420(5) . ?
C7 C8 1.350(6) . ?
C7 O2 1.371(5) . ?
C8 S2 1.721(4) . ?
C8 H8 0.95(2) . ?
C9 O1 1.461(5) . ?
C9 C10 1.489(6) . ?
C9 H9A 0.96(5) . ?
C9 H9B 0.94(5) . ?
C10 O2 1.434(5) . ?
C10 H10A 0.87(5) . ?
C10 H10B 1.05(5) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21430567
