#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/32/2223256.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_2223256
loop_
_publ_author_name
'Choi, Hong Dae'
'Seo, Pil Ja'
'Son, Byeng Wha'
'Lee, Uk'
_publ_section_title
;
 2-(4-Bromophenyl)-5-fluoro-3-methylsulfinyl-1-benzofuran
;
_journal_coeditor_code           ZS2004
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2084
_journal_paper_doi               10.1107/S1600536809030190
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C15 H10 Br F O2 S'
_chemical_formula_moiety         'C15 H10 Br F O2 S'
_chemical_formula_sum            'C15 H10 Br F O2 S'
_chemical_formula_weight         353.20
_chemical_melting_point_gt       442
_chemical_melting_point_lt       443
_chemical_name_systematic
;
2-(4-Bromophenyl)-5-fluoro-3-methylsulfinyl-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                105.9890(10)
_cell_angle_beta                 114.8110(10)
_cell_angle_gamma                99.4230(10)
_cell_formula_units_Z            2
_cell_length_a                   8.6909(7)
_cell_length_b                   9.1765(7)
_cell_length_c                   10.1308(8)
_cell_measurement_reflns_used    4045
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.40
_cell_volume                     667.91(9)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_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      293(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker SMART CCD-detector'
_diffrn_measurement_method       'φ and 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  0.0164
_diffrn_reflns_av_sigmaI/netI    0.0223
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5792
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.40
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.242
_exptl_absorpt_correction_T_max  0.720
_exptl_absorpt_correction_T_min  0.461
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.756
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.556
_refine_diff_density_min         -0.519
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2861
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0237
_refine_ls_shift/su_max          0.001
_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)+(0.0263P)²+0.5235P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0581
_refine_ls_wR_factor_ref         0.0616
_reflns_number_gt                2589
_reflns_number_total             2861
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zs2004.cif
_cod_data_source_block           I
_cod_database_code               2223256
_cod_database_fobs_code          2223256
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 0.87777(3) 0.07461(3) -0.19442(3) 0.03165(8) Uani d . 1 . .
S S 0.83195(6) 0.75073(6) 0.37122(6) 0.02170(11) Uani d . 1 . .
F F 0.27524(19) 0.78610(17) 0.54077(16) 0.0402(3) Uani d . 1 . .
O O1 0.44103(18) 0.34213(15) 0.19174(16) 0.0212(3) Uani d . 1 . .
O O2 0.8984(2) 0.83704(18) 0.54254(17) 0.0315(3) Uani d . 1 . .
C C1 0.6353(2) 0.5929(2) 0.3021(2) 0.0194(4) Uani d . 1 . .
C C2 0.4984(3) 0.5994(2) 0.3476(2) 0.0200(4) Uani d . 1 . .
C C3 0.4642(3) 0.7204(3) 0.4402(2) 0.0249(4) Uani d . 1 . .
H H3 0.5391 0.8260 0.4910 0.030 Uiso calc R 1 . .
C C4 0.3134(3) 0.6731(3) 0.4513(2) 0.0278(4) Uani d . 1 . .
C C5 0.1973(3) 0.5170(3) 0.3795(3) 0.0285(5) Uani d . 1 . .
H H5 0.0969 0.4935 0.3914 0.034 Uiso calc R 1 . .
C C6 0.2324(3) 0.3962(3) 0.2896(2) 0.0262(4) Uani d . 1 . .
H H6 0.1586 0.2903 0.2410 0.031 Uiso calc R 1 . .
C C7 0.3836(3) 0.4430(2) 0.2768(2) 0.0210(4) Uani d . 1 . .
C C8 0.5949(3) 0.4379(2) 0.2100(2) 0.0196(4) Uani d . 1 . .
C C9 0.6748(2) 0.3554(2) 0.1231(2) 0.0194(4) Uani d . 1 . .
C C10 0.6747(3) 0.1994(2) 0.1089(2) 0.0236(4) Uani d . 1 . .
H H10 0.6313 0.1507 0.1612 0.028 Uiso calc R 1 . .
C C11 0.7387(3) 0.1167(2) 0.0176(2) 0.0254(4) Uani d . 1 . .
H H11 0.7386 0.0130 0.0083 0.031 Uiso calc R 1 . .
C C12 0.8029(3) 0.1910(2) -0.0596(2) 0.0219(4) Uani d . 1 . .
C C13 0.8077(3) 0.3461(2) -0.0451(2) 0.0217(4) Uani d . 1 . .
H H13 0.8534 0.3948 -0.0961 0.026 Uiso calc R 1 . .
C C14 0.7437(3) 0.4286(2) 0.0465(2) 0.0212(4) Uani d . 1 . .
H H14 0.7466 0.5330 0.0570 0.025 Uiso calc R 1 . .
C C15 0.7267(3) 0.8706(3) 0.2720(3) 0.0310(5) Uani d . 1 . .
H H15A 0.6331 0.8880 0.2950 0.047 Uiso calc R 1 . .
H H15B 0.6768 0.8163 0.1604 0.047 Uiso calc R 1 . .
H H15C 0.8138 0.9718 0.3075 0.047 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
C12 Br O2 . 1_544 165.46(7) ?
O2 S C1 . . 106.07(9) ?
O2 S C15 . . 107.01(10) ?
C1 S C15 . . 97.48(10) ?
C8 O1 C7 . . 105.92(14) ?
C8 C1 C2 . . 106.94(17) ?
C8 C1 S . . 125.96(15) ?
C2 C1 S . . 126.73(15) ?
C7 C2 C3 . . 119.59(18) ?
C7 C2 C1 . . 105.25(16) ?
C3 C2 C1 . . 135.15(19) ?
C4 C3 C2 . . 115.79(19) ?
C4 C3 H3 . . 122.1 ?
C2 C3 H3 . . 122.1 ?
F C4 C3 . . 117.9(2) ?
F C4 C5 . . 117.34(19) ?
C3 C4 C5 . . 124.73(19) ?
C4 C5 C6 . . 119.66(19) ?
C4 C5 H5 . . 120.2 ?
C6 C5 H5 . . 120.2 ?
C7 C6 C5 . . 116.0(2) ?
C7 C6 H6 . . 122.0 ?
C5 C6 H6 . . 122.0 ?
C6 C7 O1 . . 125.17(18) ?
C6 C7 C2 . . 124.19(18) ?
O1 C7 C2 . . 110.64(16) ?
C1 C8 O1 . . 111.24(16) ?
C1 C8 C9 . . 133.66(18) ?
O1 C8 C9 . . 115.03(16) ?
C14 C9 C10 . . 119.19(18) ?
C14 C9 C8 . . 120.39(17) ?
C10 C9 C8 . . 120.34(17) ?
C11 C10 C9 . . 120.58(18) ?
C11 C10 H10 . . 119.7 ?
C9 C10 H10 . . 119.7 ?
C12 C11 C10 . . 119.00(18) ?
C12 C11 H11 . . 120.5 ?
C10 C11 H11 . . 120.5 ?
C13 C12 C11 . . 121.53(18) ?
C13 C12 Br . . 119.15(15) ?
C11 C12 Br . . 119.28(15) ?
C12 C13 C14 . . 119.28(18) ?
C12 C13 H13 . . 120.4 ?
C14 C13 H13 . . 120.4 ?
C13 C14 C9 . . 120.40(18) ?
C13 C14 H14 . . 119.8 ?
C9 C14 H14 . . 119.8 ?
S C15 H15A . . 109.5 ?
S C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
S C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 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 C12 . 1.897(2) ?
Br O2 1_544 3.036(2) ?
S C1 . 1.771(2) ?
S C15 . 1.796(2) ?
F C4 . 1.361(2) ?
O1 C8 . 1.383(2) ?
O1 C7 . 1.386(2) ?
C1 C8 . 1.359(3) ?
C1 C2 . 1.449(3) ?
C2 C7 . 1.391(3) ?
C2 C3 . 1.404(3) ?
C3 C4 . 1.373(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.391(3) ?
C5 C6 . 1.392(3) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.384(3) ?
C6 H6 . 0.9300 ?
C8 C9 . 1.466(3) ?
C9 C14 . 1.398(3) ?
C9 C10 . 1.398(3) ?
C10 C11 . 1.388(3) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.387(3) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.382(3) ?
C13 C14 . 1.388(3) ?
C13 H13 . 0.9300 ?
C14 H14 . 0.9300 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C15 H15C O2 2_776 0.96 2.36 3.251(3) 155 yes
C13 H13 Cg 2_665 0.93 2.74 3.366(3) 125 yes
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 . . . . -132.93(17) ?
C15 S C1 C8 . . . . 116.90(18) ?
O2 S C1 C2 . . . . 39.08(19) ?
C15 S C1 C2 . . . . -71.09(18) ?
C8 C1 C2 C7 . . . . 0.0(2) ?
S C1 C2 C7 . . . . -173.23(15) ?
C8 C1 C2 C3 . . . . 179.5(2) ?
S C1 C2 C3 . . . . 6.3(3) ?
C7 C2 C3 C4 . . . . -1.2(3) ?
C1 C2 C3 C4 . . . . 179.4(2) ?
C2 C3 C4 F . . . . 179.60(17) ?
C2 C3 C4 C5 . . . . 0.6(3) ?
F C4 C5 C6 . . . . -178.56(18) ?
C3 C4 C5 C6 . . . . 0.4(3) ?
C4 C5 C6 C7 . . . . -0.8(3) ?
C5 C6 C7 O1 . . . . -179.26(17) ?
C5 C6 C7 C2 . . . . 0.2(3) ?
C8 O1 C7 C6 . . . . 179.56(19) ?
C8 O1 C7 C2 . . . . 0.0(2) ?
C3 C2 C7 C6 . . . . 0.8(3) ?
C1 C2 C7 C6 . . . . -179.57(18) ?
C3 C2 C7 O1 . . . . -179.62(16) ?
C1 C2 C7 O1 . . . . 0.0(2) ?
C2 C1 C8 O1 . . . . 0.0(2) ?
S C1 C8 O1 . . . . 173.31(13) ?
C2 C1 C8 C9 . . . . 176.90(19) ?
S C1 C8 C9 . . . . -9.8(3) ?
C7 O1 C8 C1 . . . . 0.0(2) ?
C7 O1 C8 C9 . . . . -177.54(15) ?
C1 C8 C9 C14 . . . . -37.8(3) ?
O1 C8 C9 C14 . . . . 139.07(18) ?
C1 C8 C9 C10 . . . . 145.6(2) ?
O1 C8 C9 C10 . . . . -37.6(2) ?
C14 C9 C10 C11 . . . . -1.3(3) ?
C8 C9 C10 C11 . . . . 175.46(18) ?
C9 C10 C11 C12 . . . . 0.0(3) ?
C10 C11 C12 C13 . . . . 1.3(3) ?
C10 C11 C12 Br . . . . -176.36(15) ?
C11 C12 C13 C14 . . . . -1.3(3) ?
Br C12 C13 C14 . . . . 176.41(14) ?
C12 C13 C14 C9 . . . . -0.1(3) ?
C10 C9 C14 C13 . . . . 1.3(3) ?
C8 C9 C14 C13 . . . . -175.41(17) ?
