#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/59/2225936.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_2225936
loop_
_publ_author_name
'Choi, Hong Dae'
'Seo, Pil Ja'
'Son, Byeng Wha'
'Lee, Uk'
_publ_section_title
;
 5-Bromo-3-ethylsulfinyl-2-(4-fluorophenyl)-7-methyl-1-benzofuran
;
_journal_coeditor_code           NG2754
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1042
_journal_paper_doi               10.1107/S1600536810011906
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C17 H14 Br F O2 S'
_chemical_formula_moiety         'C17 H14 Br F O2 S'
_chemical_formula_sum            'C17 H14 Br F O2 S'
_chemical_formula_weight         381.25
_chemical_name_systematic
;
5-Bromo-3-ethylsulfinyl-2-(4-fluorophenyl)-7-methyl-1-benzofuran
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                111.555(2)
_cell_angle_beta                 94.643(2)
_cell_angle_gamma                108.900(2)
_cell_formula_units_Z            2
_cell_length_a                   7.3446(2)
_cell_length_b                   10.6107(3)
_cell_length_c                   11.3132(5)
_cell_measurement_reflns_used    8577
_cell_measurement_temperature    174(2)
_cell_measurement_theta_max      27.55
_cell_measurement_theta_min      2.23
_cell_volume                     755.49(5)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      174(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Bruker HELIOS graded multilayer optics'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_sigmaI/netI    0.0300
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13244
_diffrn_reflns_theta_full        27.60
_diffrn_reflns_theta_max         27.60
_diffrn_reflns_theta_min         1.99
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.873
_exptl_absorpt_correction_T_max  0.6741
_exptl_absorpt_correction_T_min  0.4705
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.676
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.576
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3493
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0260
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0335P)²+0.2459P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0668
_refine_ls_wR_factor_ref         0.0681
_reflns_number_gt                3194
_reflns_number_total             3493
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ng2754.cif
_cod_data_source_block           I
_cod_original_cell_volume        755.49(4)
_cod_database_code               2225936
_cod_database_fobs_code          2225936
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 Br 0.20782(3) 0.72623(2) 1.086606(16) 0.03206(8) Uani d . 1 . .
S S 0.05552(6) 0.19539(4) 0.57197(4) 0.02301(10) Uani d . 1 . .
F F 0.24222(19) 0.15769(15) -0.03546(11) 0.0455(3) Uani d . 1 . .
O O1 0.27205(17) 0.57068(12) 0.53317(11) 0.0219(2) Uani d . 1 . .
O O2 -0.10175(19) 0.19674(15) 0.64784(14) 0.0345(3) Uani d . 1 . .
C C1 0.1662(2) 0.37550(18) 0.58283(16) 0.0203(3) Uani d . 1 . .
C C2 0.2030(2) 0.50589(18) 0.69956(16) 0.0209(3) Uani d . 1 . .
C C3 0.1867(2) 0.53431(19) 0.82812(16) 0.0234(3) Uani d . 1 . .
H H3 0.1451 0.4580 0.8568 0.028 Uiso calc R 1 . .
C C4 0.2345(2) 0.67946(19) 0.91155(17) 0.0241(3) Uani d . 1 . .
C C5 0.2930(2) 0.79348(19) 0.87163(17) 0.0240(3) Uani d . 1 . .
H H5 0.3218 0.8909 0.9329 0.029 Uiso calc R 1 . .
C C6 0.3099(2) 0.76755(18) 0.74429(17) 0.0222(3) Uani d . 1 . .
C C7 0.2652(2) 0.62129(18) 0.66271(16) 0.0205(3) Uani d . 1 . .
C C8 0.2100(2) 0.41988(18) 0.48532(16) 0.0203(3) Uani d . 1 . .
C C9 0.2121(2) 0.34816(19) 0.34813(16) 0.0219(3) Uani d . 1 . .
C C10 0.2479(3) 0.4298(2) 0.27369(17) 0.0268(4) Uani d . 1 . .
H H10 0.2651 0.5301 0.3121 0.032 Uiso calc R 1 . .
C C11 0.2587(3) 0.3664(2) 0.14460(18) 0.0320(4) Uani d . 1 . .
H H11 0.2851 0.4224 0.0945 0.038 Uiso calc R 1 . .
C C12 0.2301(3) 0.2198(2) 0.09087(16) 0.0312(4) Uani d . 1 . .
C C13 0.1893(3) 0.1346(2) 0.15890(18) 0.0306(4) Uani d . 1 . .
H H13 0.1662 0.0333 0.1181 0.037 Uiso calc R 1 . .
C C14 0.1825(3) 0.1992(2) 0.28841(17) 0.0276(4) Uani d . 1 . .
H H14 0.1575 0.1420 0.3375 0.033 Uiso calc R 1 . .
C C15 0.3686(3) 0.8872(2) 0.69820(19) 0.0295(4) Uani d . 1 . .
H H15A 0.3548 0.9744 0.7611 0.044 Uiso calc R 1 . .
H H15B 0.2831 0.8545 0.6129 0.044 Uiso calc R 1 . .
H H15C 0.5064 0.9112 0.6904 0.044 Uiso calc R 1 . .
C C16 0.2622(3) 0.1950(2) 0.66993(18) 0.0287(4) Uani d . 1 . .
H H16A 0.3245 0.2902 0.7471 0.034 Uiso calc R 1 . .
H H16B 0.2152 0.1168 0.7010 0.034 Uiso calc R 1 . .
C C17 0.4128(3) 0.1691(2) 0.5895(2) 0.0319(4) Uani d . 1 . .
H H17A 0.3523 0.0730 0.5152 0.048 Uiso calc R 1 . .
H H17B 0.5264 0.1721 0.6439 0.048 Uiso calc R 1 . .
H H17C 0.4571 0.2456 0.5575 0.048 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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
C4 Br O2 . 2_567 170.73(6) ?
O2 S C1 . . 106.31(8) ?
O2 S C16 . . 107.61(9) ?
C1 S C16 . . 97.95(8) ?
C7 O1 C8 . . 107.02(12) ?
C8 C1 C2 . . 107.05(14) ?
C8 C1 S . . 128.90(13) ?
C2 C1 S . . 123.59(12) ?
C7 C2 C3 . . 119.53(15) ?
C7 C2 C1 . . 105.42(14) ?
C3 C2 C1 . . 135.05(16) ?
C4 C3 C2 . . 116.47(15) ?
C4 C3 H3 . . 121.8 ?
C2 C3 H3 . . 121.8 ?
C3 C4 C5 . . 123.00(16) ?
C3 C4 Br . . 118.94(13) ?
C5 C4 Br . . 117.99(13) ?
C6 C5 C4 . . 121.42(16) ?
C6 C5 H5 . . 119.3 ?
C4 C5 H5 . . 119.3 ?
C5 C6 C7 . . 114.64(15) ?
C5 C6 C15 . . 122.56(16) ?
C7 C6 C15 . . 122.79(16) ?
O1 C7 C2 . . 110.53(14) ?
O1 C7 C6 . . 124.55(15) ?
C2 C7 C6 . . 124.91(15) ?
C1 C8 O1 . . 109.97(14) ?
C1 C8 C9 . . 135.84(15) ?
O1 C8 C9 . . 114.16(14) ?
C10 C9 C14 . . 118.50(16) ?
C10 C9 C8 . . 119.51(16) ?
C14 C9 C8 . . 121.98(15) ?
C11 C10 C9 . . 120.97(17) ?
C11 C10 H10 . . 119.5 ?
C9 C10 H10 . . 119.5 ?
C12 C11 C10 . . 118.21(18) ?
C12 C11 H11 . . 120.9 ?
C10 C11 H11 . . 120.9 ?
F C12 C13 . . 118.78(18) ?
F C12 C11 . . 118.35(17) ?
C13 C12 C11 . . 122.88(17) ?
C12 C13 C14 . . 118.59(18) ?
C12 C13 H13 . . 120.7 ?
C14 C13 H13 . . 120.7 ?
C13 C14 C9 . . 120.82(17) ?
C13 C14 H14 . . 119.6 ?
C9 C14 H14 . . 119.6 ?
C6 C15 H15A . . 109.5 ?
C6 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C6 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C17 C16 S . . 109.86(13) ?
C17 C16 H16A . . 109.7 ?
S C16 H16A . . 109.7 ?
C17 C16 H16B . . 109.7 ?
S C16 H16B . . 109.7 ?
H16A C16 H16B . . 108.2 ?
C16 C17 H17A . . 109.5 ?
C16 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C16 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
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
Br C4 . 1.900(2) ?
Br O2 2_567 3.0480(10) ?
S O2 . 1.4950(10) ?
S C1 . 1.770(2) ?
S C16 . 1.808(2) ?
F C12 . 1.361(2) ?
O1 C7 . 1.375(2) ?
O1 C8 . 1.383(2) ?
C1 C8 . 1.372(2) ?
C1 C2 . 1.445(2) ?
C2 C7 . 1.388(2) ?
C2 C3 . 1.396(2) ?
C3 C4 . 1.384(2) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.396(2) ?
C5 C6 . 1.388(2) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.391(2) ?
C6 C15 . 1.496(2) ?
C8 C9 . 1.460(2) ?
C9 C10 . 1.397(2) ?
C9 C14 . 1.404(2) ?
C10 C11 . 1.387(3) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.381(3) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.369(3) ?
C13 C14 . 1.384(3) ?
C13 H13 . 0.9500 ?
C14 H14 . 0.9500 ?
C15 H15A . 0.9800 ?
C15 H15B . 0.9800 ?
C15 H15C . 0.9800 ?
C16 C17 . 1.517(3) ?
C16 H16A . 0.9900 ?
C16 H16B . 0.9900 ?
C17 H17A . 0.9800 ?
C17 H17B . 0.9800 ?
C17 H17C . 0.9800 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O2 S C1 C8 . . . . -132.95(15) ?
C16 S C1 C8 . . . . 116.00(16) ?
O2 S C1 C2 . . . . 38.33(15) ?
C16 S C1 C2 . . . . -72.72(15) ?
C8 C1 C2 C7 . . . . 0.71(17) ?
S C1 C2 C7 . . . . -172.20(12) ?
C8 C1 C2 C3 . . . . 179.68(18) ?
S C1 C2 C3 . . . . 6.8(3) ?
C7 C2 C3 C4 . . . . 0.2(2) ?
C1 C2 C3 C4 . . . . -178.62(17) ?
C2 C3 C4 C5 . . . . 1.1(2) ?
C2 C3 C4 Br . . . . 177.98(12) ?
C3 C4 C5 C6 . . . . -1.1(3) ?
Br C4 C5 C6 . . . . -178.01(12) ?
C4 C5 C6 C7 . . . . -0.3(2) ?
C4 C5 C6 C15 . . . . 178.82(16) ?
C8 O1 C7 C2 . . . . 0.99(17) ?
C8 O1 C7 C6 . . . . -177.55(15) ?
C3 C2 C7 O1 . . . . 179.79(14) ?
C1 C2 C7 O1 . . . . -1.05(17) ?
C3 C2 C7 C6 . . . . -1.7(2) ?
C1 C2 C7 C6 . . . . 177.48(15) ?
C5 C6 C7 O1 . . . . 179.99(14) ?
C15 C6 C7 O1 . . . . 0.9(3) ?
C5 C6 C7 C2 . . . . 1.6(2) ?
C15 C6 C7 C2 . . . . -177.44(16) ?
C2 C1 C8 O1 . . . . -0.13(17) ?
S C1 C8 O1 . . . . 172.28(12) ?
C2 C1 C8 C9 . . . . 177.69(17) ?
S C1 C8 C9 . . . . -9.9(3) ?
C7 O1 C8 C1 . . . . -0.51(17) ?
C7 O1 C8 C9 . . . . -178.85(13) ?
C1 C8 C9 C10 . . . . 173.69(18) ?
O1 C8 C9 C10 . . . . -8.5(2) ?
C1 C8 C9 C14 . . . . -7.4(3) ?
O1 C8 C9 C14 . . . . 170.35(14) ?
C14 C9 C10 C11 . . . . -1.5(3) ?
C8 C9 C10 C11 . . . . 177.43(15) ?
C9 C10 C11 C12 . . . . 1.0(3) ?
C10 C11 C12 F . . . . -179.44(15) ?
C10 C11 C12 C13 . . . . 0.8(3) ?
F C12 C13 C14 . . . . 178.23(16) ?
C11 C12 C13 C14 . . . . -2.0(3) ?
C12 C13 C14 C9 . . . . 1.5(3) ?
C10 C9 C14 C13 . . . . 0.3(3) ?
C8 C9 C14 C13 . . . . -178.65(15) ?
O2 S C16 C17 . . . . 170.98(13) ?
C1 S C16 C17 . . . . -79.03(14) ?
