#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/56/2205654.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_2205654
loop_
_publ_author_name
'Büyükgüngör, Orhan'
'Koşar, Başak'
'Demircan, Aydın'
'Turaç, Ersen'
_publ_section_title
;
 6-Bromo-8-thia-1,4-epoxybicyclo[4.3.0]non-2-ene
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1441
_journal_page_last               o1442
_journal_paper_doi               10.1107/S1600536805012122
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C8 H9 Br O S'
_chemical_formula_moiety         'C8 H9 Br O S'
_chemical_formula_sum            'C8 H9 Br O S'
_chemical_formula_weight         233.12
_chemical_name_systematic
;
6-Bromo-8-Thio-1,4-Epoxybicyclo[4.3.0]non-2-ene
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                81.030(12)
_cell_angle_beta                 88.572(12)
_cell_angle_gamma                81.179(12)
_cell_formula_units_Z            2
_cell_length_a                   6.6508(10)
_cell_length_b                   7.9576(12)
_cell_length_c                   8.4012(12)
_cell_measurement_reflns_used    4150
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.00
_cell_measurement_theta_min      2.45
_cell_volume                     434.00(11)
_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      296(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'STOE IPDS-II'
_diffrn_measurement_method       'ω rotation method'
_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  0.0782
_diffrn_reflns_av_sigmaI/netI    0.0595
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5151
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.62
_diffrn_standards_decay_%        <2
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.913
_exptl_absorpt_correction_T_max  0.6309
_exptl_absorpt_correction_T_min  0.3709
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'X-RED (Stoe & Cie, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.784
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             232
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.787
_refine_diff_density_min         -0.446
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1704
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0394
_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)+(0.038P)²+0.022P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0883
_refine_ls_wR_factor_ref         0.0929
_reflns_number_gt                1436
_reflns_number_total             1704
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt6650.cif
_cod_data_source_block           2a
_cod_original_sg_symbol_Hall     -P1
_cod_database_code               2205654
_cod_database_fobs_code          2205654
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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_type_symbol
C1 0.9614(6) 0.2614(5) 0.4466(5) 0.0529(9) Uani d . 1 C
H1A 1.0560 0.3429 0.4469 0.063 Uiso calc R 1 H
H1B 1.0377 0.1460 0.4634 0.063 Uiso calc R 1 H
C2 0.8496(5) 0.2944(4) 0.2883(5) 0.0434(8) Uani d . 1 C
C3 0.9471(7) 0.1924(5) 0.1584(6) 0.0592(11) Uani d . 1 C
H3A 1.0809 0.1308 0.1904 0.071 Uiso calc R 1 H
H3B 0.9568 0.2659 0.0558 0.071 Uiso calc R 1 H
C4 0.7900(8) 0.0676(6) 0.1528(6) 0.0626(12) Uani d . 1 C
H4 0.8423 -0.0386 0.1103 0.075 Uiso calc R 1 H
C5 0.6025(8) 0.1721(7) 0.0691(6) 0.0697(12) Uani d . 1 C
H5 0.5585 0.1693 -0.0346 0.084 Uiso calc R 1 H
C6 0.5143(7) 0.2677(6) 0.1728(6) 0.0593(10) Uani d . 1 C
H6 0.3955 0.3468 0.1576 0.071 Uiso calc R 1 H
C7 0.6458(5) 0.2226(4) 0.3215(5) 0.0437(8) Uani d . 1 C
C8 0.5621(6) 0.2530(5) 0.4841(5) 0.0527(9) Uani d . 1 C
H8A 0.5022 0.1545 0.5355 0.063 Uiso calc R 1 H
H8B 0.4579 0.3536 0.4731 0.063 Uiso calc R 1 H
O1 0.7252(4) 0.0438(3) 0.3181(4) 0.0529(7) Uani d . 1 O
S1 0.7737(2) 0.28576(17) 0.60491(14) 0.0662(3) Uani d . 1 S
Br1 0.79531(7) 0.54368(5) 0.21367(5) 0.05661(17) Uani d . 1 Br
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
C1 0.043(2) 0.051(2) 0.062(3) -0.0052(17) -0.0083(17) -0.0003(18)
C2 0.0412(19) 0.0381(16) 0.050(2) -0.0086(15) 0.0045(15) -0.0006(14)
C3 0.060(3) 0.056(2) 0.062(3) -0.009(2) 0.020(2) -0.0131(19)
C4 0.082(3) 0.051(2) 0.060(3) -0.018(2) 0.024(2) -0.0216(19)
C5 0.080(3) 0.079(3) 0.058(3) -0.028(3) -0.008(2) -0.016(2)
C6 0.051(2) 0.061(2) 0.066(3) -0.013(2) -0.0135(19) -0.004(2)
C7 0.0388(19) 0.0388(17) 0.053(2) -0.0079(15) 0.0041(15) -0.0033(15)
C8 0.049(2) 0.051(2) 0.060(3) -0.0152(18) 0.0136(18) -0.0085(17)
O1 0.0587(16) 0.0383(13) 0.0615(17) -0.0095(12) 0.0106(13) -0.0068(11)
S1 0.0740(8) 0.0793(7) 0.0440(6) -0.0123(6) -0.0005(5) -0.0052(5)
Br1 0.0706(3) 0.0409(2) 0.0568(3) -0.01534(17) 0.00089(18) 0.00409(15)
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
C2 C1 S1 107.7(3) ?
C2 C1 H1A 110.2 ?
S1 C1 H1A 110.2 ?
C2 C1 H1B 110.2 ?
S1 C1 H1B 110.2 ?
H1A C1 H1B 108.5 ?
C1 C2 C3 115.5(3) ?
C1 C2 C7 106.5(3) ?
C3 C2 C7 102.3(3) ?
C1 C2 Br1 109.1(3) y
C3 C2 Br1 113.0(3) y
C7 C2 Br1 109.9(2) y
C2 C3 C4 100.0(3) ?
C2 C3 H3A 111.8 ?
C4 C3 H3A 111.8 ?
C2 C3 H3B 111.8 ?
C4 C3 H3B 111.8 ?
H3A C3 H3B 109.5 ?
O1 C4 C5 102.0(4) ?
O1 C4 C3 100.9(3) ?
C5 C4 C3 107.1(4) ?
O1 C4 H4 115.1 ?
C5 C4 H4 115.1 ?
C3 C4 H4 115.1 ?
C6 C5 C4 105.9(4) ?
C6 C5 H5 127.1 ?
C4 C5 H5 127.1 ?
C5 C6 C7 105.7(4) ?
C5 C6 H6 127.1 ?
C7 C6 H6 127.1 ?
O1 C7 C8 112.3(3) ?
O1 C7 C6 102.1(3) ?
C8 C7 C6 121.4(3) ?
O1 C7 C2 97.3(3) ?
C8 C7 C2 111.0(3) ?
C6 C7 C2 109.9(3) ?
C7 C8 S1 107.4(3) ?
C7 C8 H8A 110.2 ?
S1 C8 H8A 110.2 ?
C7 C8 H8B 110.2 ?
S1 C8 H8B 110.2 ?
H8A C8 H8B 108.5 ?
C4 O1 C7 95.7(3) y
C1 S1 C8 94.58(18) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 1.508(6) ?
C1 S1 1.813(4) yes
C1 H1A 0.9700 ?
C1 H1B 0.9700 ?
C2 C3 1.533(5) ?
C2 C7 1.552(5) ?
C2 Br1 1.965(3) yes
C3 C4 1.554(6) ?
C3 H3A 0.9700 ?
C3 H3B 0.9700 ?
C4 O1 1.436(5) yes
C4 C5 1.512(8) ?
C4 H4 0.9800 ?
C5 C6 1.314(7) yes
C5 H5 0.9300 ?
C6 C7 1.508(6) ?
C6 H6 0.9300 ?
C7 O1 1.444(4) yes
C7 C8 1.502(5) ?
C8 S1 1.829(4) yes
C8 H8A 0.9700 ?
C8 H8B 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 C3 -148.0(3)
S1 C1 C2 C7 -35.2(3)
S1 C1 C2 Br1 83.5(3)
C1 C2 C3 C4 110.1(4)
C7 C2 C3 C4 -5.2(4)
Br1 C2 C3 C4 -123.3(3)
C2 C3 C4 O1 -33.0(4)
C2 C3 C4 C5 73.3(4)
O1 C4 C5 C6 32.3(5)
C3 C4 C5 C6 -73.2(5)
C4 C5 C6 C7 -0.3(5)
C5 C6 C7 O1 -31.6(4)
C5 C6 C7 C8 -157.4(4)
C5 C6 C7 C2 70.8(4)
C1 C2 C7 O1 -80.4(3)
C3 C2 C7 O1 41.3(3)
Br1 C2 C7 O1 161.6(2)
C1 C2 C7 C8 36.9(4)
C3 C2 C7 C8 158.5(3)
Br1 C2 C7 C8 -81.2(3)
C1 C2 C7 C6 173.9(3)
C3 C2 C7 C6 -64.5(4)
Br1 C2 C7 C6 55.8(4)
O1 C7 C8 S1 86.5(3)
C6 C7 C8 S1 -152.5(3)
C2 C7 C8 S1 -21.2(4)
C5 C4 O1 C7 -49.4(4)
C3 C4 O1 C7 60.9(4)
C8 C7 O1 C4 -179.1(3)
C6 C7 O1 C4 49.4(4)
C2 C7 O1 C4 -62.8(3)
C2 C1 S1 C8 20.9(3)
C7 C8 S1 C1 0.3(3)
