#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/01/2210109.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_2210109
loop_
_publ_author_name
'Koşar, Başak'
'Göktürk, Ersen'
'Demircan, Aydın'
'Büyükgüngör, Orhan'
_publ_section_title
;
 5-Bromo-10-oxa-3-thiatricyclo[5.2.1.0^1,5^]dec-8-ene 3,3-dioxide
;
_journal_coeditor_code           BT2156
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3868
_journal_page_last               o3869
_journal_paper_doi               10.1107/S160053680603090X
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C8 H9 Br O3 S'
_chemical_formula_moiety         'C8 H9 Br O3 S'
_chemical_formula_sum            'C8 H9 Br O3 S'
_chemical_formula_weight         265.12
_chemical_name_systematic
;
5-Bromo-10-oxa-3-thiatricyclo[5.2.1.0^1,5^]dec-8-ene 3,3-dioxide
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.1723(6)
_cell_length_b                   10.3446(9)
_cell_length_c                   17.6278(10)
_cell_measurement_reflns_used    1326
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.20
_cell_measurement_theta_min      1.97
_cell_volume                     1854.9(2)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED (Stoe & Cie, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Stoe IPDS-2'
_diffrn_measurement_method       ω
_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  0.1022
_diffrn_reflns_av_sigmaI/netI    0.0544
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12215
_diffrn_reflns_theta_full        25.98
_diffrn_reflns_theta_max         25.98
_diffrn_reflns_theta_min         2.31
_diffrn_standards_decay_%        <2
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.626
_exptl_absorpt_correction_T_max  0.870
_exptl_absorpt_correction_T_min  0.232
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED32; Stoe & Cie, 2002)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.899
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.337
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.952
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         1823
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.952
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0354
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0240P)²+1.8112P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0620
_refine_ls_wR_factor_ref         0.0691
_reflns_number_gt                1370
_reflns_number_total             1823
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt2156.cif
_cod_data_source_block           2
_cod_database_code               2210109
_cod_database_fobs_code          2210109
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'
'-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_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
C C1 0.3675(3) 0.3491(3) 0.1318(2) 0.0289(8) Uani d . 1
C C2 0.2726(4) 0.3455(4) 0.0635(2) 0.0405(10) Uani d . 1
H H2A 0.3071 0.3934 0.0206 0.049 Uiso calc R 1
H H2B 0.1864 0.3787 0.0767 0.049 Uiso calc R 1
C C3 0.2693(5) 0.1977(5) 0.0478(3) 0.0471(11) Uani d . 1
C C4 0.3972(5) 0.1597(5) 0.0135(3) 0.0549(12) Uani d . 1
C C5 0.4847(5) 0.1633(4) 0.0686(2) 0.0457(10) Uani d . 1
C C6 0.4096(3) 0.2027(4) 0.1384(2) 0.0299(8) Uani d . 1
C C7 0.4602(3) 0.1737(4) 0.2160(2) 0.0332(8) Uani d . 1
H H7A 0.5546 0.1861 0.2181 0.040 Uiso calc R 1
H H7B 0.4404 0.0851 0.2299 0.040 Uiso calc R 1
C C8 0.3031(3) 0.3825(4) 0.2069(2) 0.0320(8) Uani d . 1
H H8A 0.2095 0.3653 0.2047 0.038 Uiso calc R 1
H H8B 0.3159 0.4733 0.2184 0.038 Uiso calc R 1
O O1 0.2818(2) 0.1473(3) 0.12498(16) 0.0391(6) Uani d . 1
O O2 0.2803(2) 0.2182(3) 0.32180(17) 0.0499(8) Uani d . 1
O O3 0.4752(2) 0.3582(3) 0.31915(16) 0.0462(7) Uani d . 1
S S1 0.37909(8) 0.28371(10) 0.27840(5) 0.0321(2) Uani d . 1
Br Br1 0.52124(3) 0.46010(4) 0.11588(2) 0.04199(13) Uani d . 1
H H3 0.189(4) 0.169(5) 0.029(3) 0.054(13) Uiso d . 1
H H5 0.579(5) 0.146(6) 0.064(3) 0.090(18) Uiso d . 1
H H4 0.411(5) 0.146(6) -0.037(3) 0.084(18) Uiso d . 1
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
_geom_angle_publ_flag
C8 C1 C2 114.6(3) ?
C8 C1 C6 105.7(3) ?
C2 C1 C6 101.8(3) ?
C8 C1 Br1 109.6(2) ?
C2 C1 Br1 113.7(3) ?
C6 C1 Br1 110.8(2) ?
C1 C2 C3 100.1(3) ?
C1 C2 H2A 111.7 ?
C3 C2 H2A 111.7 ?
C1 C2 H2B 111.7 ?
C3 C2 H2B 111.7 ?
H2A C2 H2B 109.5 ?
O1 C3 C4 102.0(3) ?
O1 C3 C2 100.6(3) ?
C4 C3 C2 108.3(4) ?
O1 C3 H3 107(3) ?
C4 C3 H3 123(3) ?
C2 C3 H3 113(3) ?
C5 C4 C3 106.5(4) ?
C5 C4 H4 128(3) ?
C3 C4 H4 125(3) ?
C4 C5 C6 105.5(4) ?
C4 C5 H5 127(4) ?
C6 C5 H5 128(4) ?
O1 C6 C7 112.5(3) ?
O1 C6 C5 102.5(3) ?
C7 C6 C5 121.3(3) ?
O1 C6 C1 97.2(2) ?
C7 C6 C1 110.8(3) ?
C5 C6 C1 109.7(3) ?
C6 C7 S1 106.1(2) ?
C6 C7 H7A 110.5 ?
S1 C7 H7A 110.5 ?
C6 C7 H7B 110.5 ?
S1 C7 H7B 110.5 ?
H7A C7 H7B 108.7 ?
C1 C8 S1 107.3(2) ?
C1 C8 H8A 110.3 ?
S1 C8 H8A 110.3 ?
C1 C8 H8B 110.3 ?
S1 C8 H8B 110.3 ?
H8A C8 H8B 108.5 ?
C6 O1 C3 95.1(3) y
O2 S1 O3 117.62(18) ?
O2 S1 C7 110.6(2) ?
O3 S1 C7 109.59(16) ?
O2 S1 C8 110.00(16) ?
O3 S1 C8 109.77(19) ?
C7 S1 C8 97.41(17) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C8 1.517(5) ?
C1 C2 1.542(5) ?
C1 C6 1.578(5) ?
C1 Br1 1.961(3) y
C2 C3 1.554(6) ?
C2 H2A 0.9700 ?
C2 H2B 0.9700 ?
C3 O1 1.463(5) y
C3 C4 1.487(7) ?
C3 H3 0.93(4) ?
C4 C5 1.318(7) ?
C4 H4 0.91(6) ?
C5 C6 1.504(5) ?
C5 H5 0.98(5) ?
C6 O1 1.440(4) y
C6 C7 1.492(5) ?
C7 S1 1.785(4) y
C7 H7A 0.9700 ?
C7 H7B 0.9700 ?
C8 S1 1.797(4) y
C8 H8A 0.9700 ?
C8 H8B 0.9700 ?
O2 S1 1.433(3) y
O3 S1 1.437(3) y
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_publ_flag
C8 C1 C2 C3 -109.4(4) ?
C6 C1 C2 C3 4.2(4) ?
Br1 C1 C2 C3 123.5(3) ?
C1 C2 C3 O1 33.9(4) y
C1 C2 C3 C4 -72.6(4) y
O1 C3 C4 C5 -32.3(5) ?
C2 C3 C4 C5 73.2(5) y
C3 C4 C5 C6 0.7(5) y
C4 C5 C6 O1 31.8(4) y
C4 C5 C6 C7 158.1(4) ?
C4 C5 C6 C1 -70.6(4) ?
C8 C1 C6 O1 78.6(3) ?
C2 C1 C6 O1 -41.5(3) ?
Br1 C1 C6 O1 -162.7(2) ?
C8 C1 C6 C7 -38.8(3) ?
C2 C1 C6 C7 -158.8(3) ?
Br1 C1 C6 C7 79.9(3) ?
C8 C1 C6 C5 -175.3(3) ?
C2 C1 C6 C5 64.6(4) ?
Br1 C1 C6 C5 -56.7(3) ?
O1 C6 C7 S1 -79.1(3) ?
C5 C6 C7 S1 159.2(3) ?
C1 C6 C7 S1 28.4(3) ?
C2 C1 C8 S1 141.4(3) ?
C6 C1 C8 S1 30.1(3) ?
Br1 C1 C8 S1 -89.4(2) ?
C7 C6 O1 C3 179.2(3) ?
C5 C6 O1 C3 -48.9(3) ?
C1 C6 O1 C3 63.2(3) ?
C4 C3 O1 C6 49.3(4) ?
C2 C3 O1 C6 -62.2(3) ?
C6 C7 S1 O2 105.8(3) ?
C6 C7 S1 O3 -122.9(2) ?
C6 C7 S1 C8 -8.8(3) ?
C1 C8 S1 O2 -128.5(3) ?
C1 C8 S1 O3 100.6(3) ?
C1 C8 S1 C7 -13.4(3) ?
