#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/19/2211967.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_2211967
loop_
_publ_author_name
'Fischer, Andreas'
'Yathirajan, H. S.'
'Ashalatha, B. V.'
'Naranaya, B.'
'Sarojini, B.K.'
_publ_section_title
;
 (8RS,9SR)-Ethyl
 4-(3-bromothien-2-yl)-6-(2-furyl)-2-oxocyclohex-3-ene-1-carboxylate
;
_journal_coeditor_code           WN2095
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o254
_journal_page_last               o255
_journal_paper_doi               10.1107/S1600536806052603
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C17 H15 Br O4 S'
_chemical_formula_moiety         'C17 H15 Br O4 S'
_chemical_formula_sum            'C17 H15 Br O4 S'
_chemical_formula_weight         395.26
_chemical_name_systematic
;
(8RS,9SR)-ethyl
4-(3-bromothien-2-yl)-6-(2-furyl)-2-oxocyclohex-3-ene-1-carboxylate
;
_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_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 100.098(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.5539(14)
_cell_length_b                   11.1125(8)
_cell_length_c                   9.1650(5)
_cell_measurement_reflns_used    136
_cell_measurement_temperature    300
_cell_measurement_theta_max      20.6
_cell_measurement_theta_min      4.1
_cell_volume                     1659.8(2)
_computing_cell_refinement       'DIRAX/LSQ (Duisenberg, 1992)'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction        'EvalCCD (Duisenberg et al.,  2003)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'maXus (Mackay et al.,  1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       'Bruker--Nonius KappaCCD'
_diffrn_measurement_method       φ
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_reflns_av_R_equivalents  0.0595
_diffrn_reflns_av_sigmaI/netI    0.0355
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            17471
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         4.52
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.619
_exptl_absorpt_correction_T_max  0.805
_exptl_absorpt_correction_T_min  0.600
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
'(HABITUS; Herrendorf & Bärnighausen, 1997)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Irregular block'
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.445
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.165
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3390
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.165
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0373
_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)+(0.025P)²+1.728P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0772
_refine_ls_wR_factor_ref         0.0900
_reflns_number_gt                2655
_reflns_number_total             3390
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wn2095.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2211967
_cod_database_fobs_code          2211967
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
Br Br1 1.07670(2) 0.26706(3) -0.00141(4) 0.05410(13) Uani d . 1
S S1 1.04563(5) 0.53429(8) 0.33347(9) 0.0452(2) Uani d . 1
C C5 0.92251(17) 0.4182(2) 0.1472(3) 0.0338(6) Uani d . 1
C C4 1.01047(18) 0.4326(3) 0.1929(3) 0.0350(6) Uani d . 1
C C9 0.78162(18) 0.4973(3) 0.1686(3) 0.0394(7) Uani d . 1
H H9 0.7850 0.5650 0.1015 0.047 Uiso calc R 1
O O2 0.73316(15) 0.6521(2) 0.3160(3) 0.0651(7) Uani d . 1
C C6 0.88879(19) 0.3613(3) 0.0225(3) 0.0411(7) Uani d . 1
H H6 0.9234 0.3319 -0.0389 0.049 Uiso calc R 1
C C3 1.07757(19) 0.3798(3) 0.1504(3) 0.0384(7) Uani d . 1
C C11 0.72925(18) 0.5341(3) 0.2772(4) 0.0431(7) Uani d . 1
C C10 0.86807(17) 0.4675(3) 0.2473(3) 0.0395(7) Uani d . 1
H H10A 0.8930 0.5399 0.2944 0.047 Uiso calc R 1
H H10B 0.8647 0.4092 0.3247 0.047 Uiso calc R 1
C C7 0.8017(2) 0.3431(3) -0.0218(3) 0.0442(7) Uani d . 1
C C1 1.14510(19) 0.5022(3) 0.3307(4) 0.0499(8) Uani d . 1
H H1 1.1890 0.5382 0.3925 0.060 Uiso calc R 1
C C2 1.15341(19) 0.4184(3) 0.2285(4) 0.0479(8) Uani d . 1
H H2 1.2037 0.3894 0.2117 0.057 Uiso calc R 1
C C8 0.74444(17) 0.3904(3) 0.0764(3) 0.0377(6) Uani d . 1
H H8 0.7340 0.3260 0.1437 0.045 Uiso calc R 1
C C15 0.6643(2) 0.4234(3) -0.0217(4) 0.0527(8) Uani d . 1
C C13 0.6539(2) 0.5617(4) 0.4510(5) 0.0713(11) Uani d . 1
H H13 0.6196 0.5475 0.5194 0.086 Uiso calc R 1
C C12 0.6816(2) 0.4759(3) 0.3561(4) 0.0584(9) Uani d . 1
H H12 0.6688 0.3944 0.3502 0.070 Uiso calc R 1
C C14 0.6862(2) 0.6645(4) 0.4231(5) 0.0745(13) Uani d . 1
H H14 0.6782 0.7366 0.4701 0.089 Uiso calc R 1
O O1 0.77427(17) 0.2894(3) -0.1356(3) 0.0696(8) Uani d . 1
O O4 0.61114(15) 0.3346(2) -0.0301(3) 0.0681(7) Uani d . 1
O O3 0.65141(18) 0.5171(3) -0.0838(3) 0.0828(9) Uani d . 1
C C16 0.5337(3) 0.3510(5) -0.1325(6) 0.1015(18) Uani d . 1
H H16A 0.5041 0.4192 -0.1020 0.122 Uiso calc R 1
H H16B 0.5442 0.3663 -0.2317 0.122 Uiso calc R 1
C C17 0.4869(4) 0.2452(7) -0.1314(9) 0.167(4) Uani d . 1
H H17A 0.4361 0.2537 -0.1995 0.250 Uiso calc R 1
H H17B 0.4757 0.2317 -0.0333 0.250 Uiso calc R 1
H H17C 0.5170 0.1781 -0.1605 0.250 Uiso calc R 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'
Br Br -0.2901 2.4595 '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'
loop_
_diffrn_radiation_wavelength
0.71073
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
C1 S1 C4 92.98(16) n
C6 C5 C4 123.0(3) n
C6 C5 C10 119.3(3) n
C4 C5 C10 117.6(2) n
C3 C4 C5 133.8(3) n
C3 C4 S1 107.9(2) n
C5 C4 S1 118.4(2) n
C11 C9 C10 110.6(2) n
C11 C9 C8 111.1(2) n
C10 C9 C8 110.4(2) n
C11 C9 H9 108.2 n
C10 C9 H9 108.2 n
C8 C9 H9 108.2 n
C11 O2 C14 106.3(3) n
C5 C6 C7 123.6(3) n
C5 C6 H6 118.2 n
C7 C6 H6 118.2 n
C4 C3 C2 115.0(3) n
C4 C3 Br1 126.7(2) n
C2 C3 Br1 118.4(2) n
C12 C11 O2 109.5(3) n
C12 C11 C9 134.6(3) n
O2 C11 C9 115.8(3) n
C5 C10 C9 114.0(2) n
C5 C10 H10A 108.8 n
C9 C10 H10A 108.8 n
C5 C10 H10B 108.8 n
C9 C10 H10B 108.8 n
H10A C10 H10B 107.7 n
O1 C7 C6 120.9(3) n
O1 C7 C8 120.1(3) n
C6 C7 C8 119.0(3) n
C2 C1 S1 112.1(2) n
C2 C1 H1 124.0 n
S1 C1 H1 124.0 n
C1 C2 C3 112.1(3) n
C1 C2 H2 123.9 n
C3 C2 H2 123.9 n
C7 C8 C15 107.9(3) n
C7 C8 C9 111.5(2) n
C15 C8 C9 111.6(3) n
C7 C8 H8 108.6 n
C15 C8 H8 108.6 n
C9 C8 H8 108.6 n
O3 C15 O4 124.5(3) n
O3 C15 C8 124.3(3) n
O4 C15 C8 111.2(3) n
C14 C13 C12 106.3(4) n
C14 C13 H13 126.9 n
C12 C13 H13 126.9 n
C11 C12 C13 107.1(4) n
C11 C12 H12 126.5 n
C13 C12 H12 126.5 n
C13 C14 O2 110.9(3) n
C13 C14 H14 124.5 n
O2 C14 H14 124.5 n
C15 O4 C16 116.6(3) n
C17 C16 O4 108.2(4) n
C17 C16 H16A 110.0 n
O4 C16 H16A 110.0 n
C17 C16 H16B 110.0 n
O4 C16 H16B 110.0 n
H16A C16 H16B 108.4 n
C16 C17 H17A 109.5 n
C16 C17 H17B 109.5 n
H17A C17 H17B 109.5 n
C16 C17 H17C 109.5 n
H17A C17 H17C 109.5 n
H17B C17 H17C 109.5 n
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C3 1.870(3) n
S1 C1 1.689(3) n
S1 C4 1.736(3) n
C5 C6 1.339(4) n
C5 C4 1.452(4) n
C5 C10 1.498(4) n
C4 C3 1.372(4) n
C9 C11 1.488(4) n
C9 C10 1.522(4) n
C9 C8 1.524(4) n
C9 H9 0.9800 n
O2 C11 1.357(4) n
O2 C14 1.362(5) n
C6 C7 1.442(4) n
C6 H6 0.9300 n
C3 C2 1.399(4) n
C11 C12 1.328(5) n
C10 H10A 0.9700 n
C10 H10B 0.9700 n
C7 O1 1.218(4) n
C7 C8 1.511(4) n
C1 C2 1.345(5) n
C1 H1 0.9300 n
C2 H2 0.9300 n
C8 C15 1.511(4) n
C8 H8 0.9800 n
C15 O3 1.188(4) n
C15 O4 1.315(4) n
C13 C14 1.306(6) n
C13 C12 1.420(5) n
C13 H13 0.9300 n
C12 H12 0.9300 n
C14 H14 0.9300 n
O4 C16 1.461(5) n
C16 C17 1.409(7) n
C16 H16A 0.9700 n
C16 H16B 0.9700 n
C17 H17A 0.9600 n
C17 H17B 0.9600 n
C17 H17C 0.9600 n
