#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:42:48 +0200 (vie 13 de oct de 2017) $
#$Revision: 201978 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/90/2229099.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2229099
loop_
_publ_author_name
'Clément, Sebastien'
'Guyard, Laurent'
'Knorr, Michael'
'Eckert, Prisca K.'
'Strohmann, Carsten'
_publ_section_title
;
 2-(2,2-Dibromoethenyl)thiophene
;
_journal_coeditor_code           IM2256
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o481
_journal_paper_doi               10.1107/S1600536811002522
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C6 H4 Br2 S'
_chemical_formula_moiety         'C6 H4 Br2 S'
_chemical_formula_sum            'C6 H4 Br2 S'
_chemical_formula_weight         267.97
_chemical_name_systematic
;
2-(2,2-Dibromoethenyl)thiophene
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_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           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 109.16(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6843(19)
_cell_length_b                   7.2379(14)
_cell_length_c                   11.484(2)
_cell_measurement_reflns_used    980
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.99
_cell_measurement_theta_min      2.23
_cell_volume                     760.4(3)
_computing_cell_refinement       'CELL in IPDS (Stoe & Cie, 1999)'
_computing_data_collection       'EXPOSE in IPDS (Stoe & Cie, 1999)'
_computing_data_reduction        'INTEGRATE in IPDS (Stoe & Cie, 1999)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Stoe IPDS'
_diffrn_measurement_method       φ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0637
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6492
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         2.23
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    10.839
_exptl_absorpt_correction_T_max  0.6584
_exptl_absorpt_correction_T_min  0.1878
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(FACEIT in IPDS; Stoe & Cie, 1999)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.358
_refine_diff_density_min         -1.732
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         1667
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0579
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1099P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1388
_reflns_number_gt                1444
_reflns_number_total             1667
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            im2256.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2229099
_cod_database_fobs_code          2229099
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.90429(5) 0.69525(7) 0.15399(5) 0.0306(2) Uani d . 1 . .
Br Br2 0.75506(5) 0.94572(7) 0.30330(4) 0.0290(2) Uani d . 1 . .
C C1 0.7287(5) 0.7946(6) 0.1647(4) 0.0214(9) Uani d . 1 . .
C C2 0.5999(5) 0.7559(7) 0.0803(4) 0.0225(9) Uani d . 1 . .
H H2 0.6061 0.6818 0.0139 0.027 Uiso calc R 1 . .
C C3 0.4530(5) 0.8068(6) 0.0720(4) 0.0188(8) Uani d . 1 . .
C C4 0.3277(5) 0.7471(7) -0.0213(4) 0.0225(9) Uani d . 1 . .
H H4 0.3305 0.6695 -0.0873 0.027 Uiso calc R 1 . .
C C5 0.1970(6) 0.8134(7) -0.0080(5) 0.0307(11) Uani d . 1 . .
H H5 0.1026 0.7857 -0.0637 0.037 Uiso calc R 1 . .
C C6 0.2213(5) 0.9216(7) 0.0939(5) 0.0289(10) Uani d . 1 . .
H H6 0.1455 0.9771 0.1174 0.035 Uiso calc R 1 . .
S S 0.40366(13) 0.94655(17) 0.17497(12) 0.0265(3) Uani d . 1 . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Br1 0.0220(3) 0.0379(4) 0.0324(3) 0.00528(18) 0.0097(2) -0.0004(2)
Br2 0.0268(3) 0.0342(3) 0.0250(3) -0.00466(18) 0.0072(2) -0.00800(17)
C1 0.024(2) 0.021(2) 0.0202(19) 0.0009(16) 0.0089(17) 0.0037(16)
C2 0.024(2) 0.020(2) 0.024(2) 0.0027(18) 0.0104(18) 0.0016(17)
C3 0.024(2) 0.0157(19) 0.0183(19) 0.0008(15) 0.0095(17) 0.0015(15)
C4 0.024(2) 0.020(2) 0.024(2) 0.0029(17) 0.0083(18) 0.0041(17)
C5 0.020(2) 0.034(3) 0.036(3) -0.0005(18) 0.005(2) 0.006(2)
C6 0.022(2) 0.028(2) 0.037(3) -0.0003(18) 0.011(2) 0.003(2)
S 0.0256(6) 0.0287(6) 0.0277(6) 0.0006(4) 0.0121(5) -0.0054(4)
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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 Br2 . . 124.9(4) ?
C2 C1 Br1 . . 121.3(4) ?
Br2 C1 Br1 . . 113.7(3) ?
C1 C2 C3 . . 131.4(4) ?
C1 C2 H2 . . 114.3 ?
C3 C2 H2 . . 114.3 ?
C4 C3 C2 . . 124.1(4) ?
C4 C3 S . . 109.8(3) ?
C2 C3 S . . 126.1(3) ?
C3 C4 C5 . . 113.3(4) ?
C3 C4 H4 . . 123.3 ?
C5 C4 H4 . . 123.3 ?
C6 C5 C4 . . 112.4(5) ?
C6 C5 H5 . . 123.8 ?
C4 C5 H5 . . 123.8 ?
C5 C6 S . . 112.6(4) ?
C5 C6 H6 . . 123.7 ?
S C6 H6 . . 123.7 ?
C6 S C3 . . 91.9(2) ?
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
Br1 C1 . 1.887(5) ?
Br2 C1 . 1.878(5) ?
C1 C2 . 1.335(7) ?
C2 C3 . 1.442(6) ?
C2 H2 . 0.95 ?
C3 C4 . 1.397(7) ?
C3 S . 1.738(4) ?
C4 C5 . 1.408(7) ?
C4 H4 . 0.95 ?
C5 C6 . 1.362(8) ?
C5 H5 . 0.95 ?
C6 S . 1.714(5) ?
C6 H6 . 0.95 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9382956
