#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/06/2210682.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_2210682
loop_
_publ_author_name
'Choi, Hong Dae'
'Woo, Hyun Mi'
'Seo,  Pil Ja'
'Son, Byeng Wha'
'Lee, Uk'
_publ_section_title
;
 5-(4-Bromophenyl)-3-methylsulfanyl-2-phenyl-1-benzofuran
;
_journal_coeditor_code           JH2036
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4708
_journal_page_last               o4709
_journal_paper_doi               10.1107/S1600536806038311
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C21 H15 Br O S'
_chemical_formula_moiety         'C21 H15 Br O S'
_chemical_formula_sum            'C21 H15 Br O S'
_chemical_formula_weight         395.30
_chemical_name_systematic
;
5-(4-Bromophenyl)-3-methylsulfanyl-2-phenyl-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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                101.4760(10)
_cell_angle_beta                 107.0910(10)
_cell_angle_gamma                90.9290(10)
_cell_formula_units_Z            2
_cell_length_a                   7.7452(5)
_cell_length_b                   9.2404(6)
_cell_length_c                   12.6789(9)
_cell_measurement_reflns_used    5108
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.23
_cell_measurement_theta_min      2.26
_cell_volume                     847.30(10)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997\\bbr00)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker SMART CCD'
_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  0.0449
_diffrn_reflns_av_sigmaI/netI    0.0383
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7306
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.26
_exptl_absorpt_coefficient_mu    2.553
_exptl_absorpt_correction_T_max  0.357
_exptl_absorpt_correction_T_min  0.198
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1999)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.60
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.463
_refine_diff_density_min         -0.546
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3629
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.979
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0304
_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)+(0.0537P)²+0.2432P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0812
_refine_ls_wR_factor_ref         0.0830
_reflns_number_gt                3270
_reflns_number_total             3629
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jh2036.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     -P_1
_cod_database_code               2210682
_cod_database_fobs_code          2210682
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
Br Br 1.16521(3) 0.73729(2) 0.206551(19) 0.03910(10) Uani d . 1
S S 0.23695(6) 0.34530(5) 0.47028(4) 0.02792(12) Uani d . 1
O O 0.01297(17) 0.12375(14) 0.15388(11) 0.0248(3) Uani d . 1
C C1 0.9460(2) 0.6248(2) 0.18811(16) 0.0261(4) Uani d . 1
C C2 0.9082(3) 0.4869(2) 0.11712(16) 0.0281(4) Uani d . 1
H H2 0.9878 0.4494 0.0780 0.034 Uiso calc R 1
C C3 0.7492(3) 0.4048(2) 0.10485(16) 0.0265(4) Uani d . 1
H H3 0.7221 0.3120 0.0565 0.032 Uiso calc R 1
C C4 0.6287(2) 0.45922(19) 0.16395(14) 0.0223(3) Uani d . 1
C C5 0.6711(2) 0.6005(2) 0.23375(15) 0.0246(4) Uani d . 1
H H5 0.5915 0.6393 0.2725 0.029 Uiso calc R 1
C C6 0.8293(3) 0.6845(2) 0.24669(15) 0.0267(4) Uani d . 1
H H6 0.8562 0.7783 0.2935 0.032 Uiso calc R 1
C C7 0.4641(2) 0.36815(19) 0.15692(15) 0.0225(3) Uani d . 1
C C8 0.3602(3) 0.2764(2) 0.05370(15) 0.0246(4) Uani d . 1
H H8 0.3959 0.2742 -0.0105 0.030 Uiso calc R 1
C C9 0.2070(3) 0.1898(2) 0.04485(15) 0.0253(4) Uani d . 1
H H9 0.1391 0.1296 -0.0233 0.030 Uiso calc R 1
C C10 0.1606(2) 0.19775(19) 0.14326(15) 0.0224(3) Uani d . 1
C C11 0.0186(2) 0.16648(19) 0.26632(15) 0.0237(4) Uani d . 1
C C12 0.1668(2) 0.2629(2) 0.32613(15) 0.0236(3) Uani d . 1
C C13 0.2596(2) 0.28571(19) 0.24663(14) 0.0222(3) Uani d . 1
C C14 0.4131(2) 0.37258(19) 0.25384(15) 0.0227(3) Uani d . 1
H H14 0.4803 0.4325 0.3223 0.027 Uiso calc R 1
C C15 -0.1351(3) 0.10619(19) 0.29357(16) 0.0257(4) Uani d . 1
C C16 -0.2968(3) 0.0530(2) 0.20733(18) 0.0303(4) Uani d . 1
H H16 -0.3045 0.0534 0.1328 0.036 Uiso calc R 1
C C17 -0.4453(3) -0.0003(2) 0.2325(2) 0.0379(5) Uani d . 1
H H17 -0.5521 -0.0355 0.1749 0.045 Uiso calc R 1
C C18 -0.4345(3) -0.0011(3) 0.3431(2) 0.0426(5) Uani d . 1
H H18 -0.5346 -0.0356 0.3600 0.051 Uiso calc R 1
C C19 -0.2757(4) 0.0490(3) 0.4284(2) 0.0444(6) Uani d . 1
H H19 -0.2687 0.0473 0.5026 0.053 Uiso calc R 1
C C20 -0.1258(3) 0.1022(2) 0.40434(18) 0.0354(5) Uani d . 1
H H20 -0.0189 0.1352 0.4624 0.043 Uiso calc R 1
C C21 0.2047(3) 0.5374(2) 0.46534(19) 0.0366(5) Uani d . 1
H H21A 0.2393 0.5964 0.5408 0.044 Uiso calc R 1
H H21B 0.0796 0.5474 0.4283 0.044 Uiso calc R 1
H H21C 0.2783 0.5705 0.4242 0.044 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'
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
C12 S C21 100.89(9) yes
C10 O C11 106.40(10) yes
C2 C1 C6 121.96(17) ?
C2 C1 Br 119.20(10) yes
C6 C1 Br 118.90(10) yes
C1 C2 C3 118.92(17) ?
C1 C2 H2 120.5 ?
C3 C2 H2 120.5 ?
C2 C3 C4 121.20(17) ?
C2 C3 H3 119.4 ?
C4 C3 H3 119.4 ?
C3 C4 C5 117.97(17) ?
C3 C4 C7 121.51(16) ?
C5 C4 C7 120.47(16) ?
C6 C5 C4 121.57(17) ?
C6 C5 H5 119.2 ?
C4 C5 H5 119.2 ?
C5 C6 C1 118.35(17) ?
C5 C6 H6 120.8 ?
C1 C6 H6 120.8 ?
C14 C7 C8 119.70(16) ?
C14 C7 C4 119.30(16) ?
C8 C7 C4 120.99(16) ?
C9 C8 C7 122.23(16) ?
C9 C8 H8 118.9 ?
C7 C8 H8 118.9 ?
C10 C9 C8 116.23(16) ?
C10 C9 H9 121.9 ?
C8 C9 H9 121.9 ?
C13 C10 O 110.37(15) ?
C13 C10 C9 123.39(16) ?
O C10 C9 126.23(16) ?
C12 C11 O 110.72(15) ?
C12 C11 C15 134.38(17) ?
O C11 C15 114.82(16) ?
C11 C12 C13 106.50(15) ?
C11 C12 S 128.46(14) ?
C13 C12 S 125.03(14) ?
C10 C13 C14 119.57(16) ?
C10 C13 C12 105.97(15) ?
C14 C13 C12 134.45(16) ?
C7 C14 C13 118.87(16) ?
C7 C14 H14 120.6 ?
C13 C14 H14 120.6 ?
C20 C15 C16 118.73(18) ?
C20 C15 C11 121.38(18) ?
C16 C15 C11 119.88(18) ?
C17 C16 C15 120.4(2) ?
C17 C16 H16 119.8 ?
C15 C16 H16 119.8 ?
C18 C17 C16 120.0(2) ?
C18 C17 H17 120.0 ?
C16 C17 H17 120.0 ?
C19 C18 C17 120.0(2) ?
C19 C18 H18 120.0 ?
C17 C18 H18 120.0 ?
C18 C19 C20 120.5(2) ?
C18 C19 H19 119.7 ?
C20 C19 H19 119.7 ?
C19 C20 C15 120.2(2) ?
C19 C20 H20 119.9 ?
C15 C20 H20 119.9 ?
S C21 H21A 109.5 ?
S C21 H21B 109.5 ?
H21A C21 H21B 109.5 ?
S C21 H21C 109.5 ?
H21A C21 H21C 109.5 ?
H21B C21 H21C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Br C1 1.905(2) yes
S C12 1.751(2) yes
S C21 1.808(2) yes
O C10 1.377(2) yes
O C11 1.389(2) yes
C1 C2 1.377(3) ?
C1 C6 1.386(3) ?
C2 C3 1.388(3) ?
C2 H2 0.9300 ?
C3 C4 1.400(3) ?
C3 H3 0.9300 ?
C4 C5 1.397(2) ?
C4 C7 1.487(2) ?
C5 C6 1.390(3) ?
C5 H5 0.9300 ?
C6 H6 0.9300 ?
C7 C14 1.391(2) ?
C7 C8 1.413(3) ?
C8 C9 1.384(3) ?
C8 H8 0.9300 ?
C9 C10 1.386(3) ?
C9 H9 0.9300 ?
C10 C13 1.390(2) ?
C11 C12 1.368(3) ?
C11 C15 1.464(3) ?
C12 C13 1.444(2) ?
C13 C14 1.393(2) ?
C14 H14 0.9300 ?
C15 C20 1.393(3) ?
C15 C16 1.402(3) ?
C16 C17 1.388(3) ?
C16 H16 0.9300 ?
C17 C18 1.382(4) ?
C17 H17 0.9300 ?
C18 C19 1.377(4) ?
C18 H18 0.9300 ?
C19 C20 1.389(3) ?
C19 H19 0.9300 ?
C20 H20 0.9300 ?
C21 H21A 0.9600 ?
C21 H21B 0.9600 ?
C21 H21C 0.9600 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21127212
