#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/93/2239309.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_2239309
loop_
_publ_author_name
'Choi, Hong Dae'
'Seo, Pil Ja'
'Lee, Uk'
_publ_section_title
;
 5-Bromo-2,7-dimethyl-3-(4-methylphenylsulfonyl)-1-benzofuran
;
_journal_coeditor_code           GG2139
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o520
_journal_paper_doi               10.1107/S1600536814007181
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C17 H15 Br O3 S'
_chemical_formula_moiety         'C17 H15 Br O3 S'
_chemical_formula_sum            'C17 H15 Br O3 S'
_chemical_formula_weight         379.26
_chemical_melting_point_gt       475
_chemical_melting_point_lt       474
_chemical_name_systematic
;
5-Bromo-2,7-dimethyl-3-(4-methylphenylsulfonyl)-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
_audit_creation_method           'form.cif (version 2.0)'
_cell_angle_alpha                77.4100(10)
_cell_angle_beta                 77.1140(10)
_cell_angle_gamma                76.0090(10)
_cell_formula_units_Z            2
_cell_length_a                   8.1554(2)
_cell_length_b                   9.9790(2)
_cell_length_c                   10.1260(2)
_cell_measurement_reflns_used    6793
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.33
_cell_measurement_theta_min      2.72
_cell_volume                     767.68(3)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics
;
ORTEP-3 for Windows  (Farrugia, 2012) 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      173(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'graphite multilayer'
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_sigmaI/netI    0.0292
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14016
_diffrn_reflns_theta_full        28.37
_diffrn_reflns_theta_max         28.37
_diffrn_reflns_theta_min         2.09
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.823
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5425
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.641
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.420
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3812
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0278
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0353P)²+0.3958P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0701
_refine_ls_wR_factor_ref         0.0733
_reflns_number_gt                3336
_reflns_number_total             3812
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gg2139sup1.cif
_cod_data_source_block           I
_cod_database_code               2239309
_cod_database_fobs_code          2239309
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_symmetry_multiplicity
Br Br1 0.50946(3) 0.81656(2) -0.00546(2) 0.03262(8) Uani d . 1 1
S S1 0.91173(6) 0.31301(5) 0.35042(4) 0.02099(10) Uani d . 1 1
O O1 0.93317(17) 0.24115(13) -0.01983(13) 0.0222(3) Uani d . 1 1
O O2 0.88773(18) 0.45707(15) 0.36343(14) 0.0274(3) Uani d . 1 1
O O3 1.06161(18) 0.21433(15) 0.38771(14) 0.0287(3) Uani d . 1 1
C C1 0.9028(2) 0.31299(19) 0.18034(17) 0.0199(3) Uani d . 1 1
C C2 0.8119(2) 0.42615(19) 0.09103(18) 0.0195(3) Uani d . 1 1
C C3 0.7156(2) 0.56082(19) 0.10102(19) 0.0225(4) Uani d . 1 1
H H3 0.6982 0.6000 0.1818 0.027 Uiso calc R 1 1
C C4 0.6470(2) 0.63398(19) -0.01324(19) 0.0232(4) Uani d . 1 1
C C5 0.6705(3) 0.5809(2) -0.13421(19) 0.0251(4) Uani d . 1 1
H H5 0.6202 0.6369 -0.2094 0.030 Uiso calc R 1 1
C C6 0.7667(2) 0.4471(2) -0.14618(18) 0.0230(4) Uani d . 1 1
C C7 0.8346(2) 0.37528(19) -0.03066(18) 0.0205(3) Uani d . 1 1
C C8 0.9720(2) 0.2055(2) 0.10962(18) 0.0217(4) Uani d . 1 1
C C9 0.7931(3) 0.3831(2) -0.2723(2) 0.0308(4) Uani d . 1 1
H H9A 0.9106 0.3284 -0.2890 0.046 Uiso calc R 1 1
H H9B 0.7745 0.4576 -0.3516 0.046 Uiso calc R 1 1
H H9C 0.7114 0.3215 -0.2585 0.046 Uiso calc R 1 1
C C10 1.0746(3) 0.0626(2) 0.1429(2) 0.0284(4) Uani d . 1 1
H H10A 1.0974 0.0473 0.2366 0.043 Uiso calc R 1 1
H H10B 1.1838 0.0523 0.0778 0.043 Uiso calc R 1 1
H H10C 1.0108 -0.0065 0.1363 0.043 Uiso calc R 1 1
C C11 0.7293(2) 0.25019(19) 0.44768(18) 0.0206(3) Uani d . 1 1
C C12 0.5677(3) 0.3361(2) 0.4457(2) 0.0270(4) Uani d . 1 1
H H12 0.5553 0.4269 0.3908 0.032 Uiso calc R 1 1
C C13 0.4250(3) 0.2879(2) 0.5248(2) 0.0295(4) Uani d . 1 1
H H13 0.3142 0.3461 0.5232 0.035 Uiso calc R 1 1
C C14 0.4410(3) 0.1561(2) 0.60634(19) 0.0267(4) Uani d . 1 1
C C15 0.6032(3) 0.0716(2) 0.6056(2) 0.0303(4) Uani d . 1 1
H H15 0.6155 -0.0193 0.6604 0.036 Uiso calc R 1 1
C C16 0.7476(3) 0.1173(2) 0.5263(2) 0.0269(4) Uani d . 1 1
H H16 0.8580 0.0580 0.5260 0.032 Uiso calc R 1 1
C C17 0.2839(3) 0.1074(3) 0.6937(2) 0.0375(5) Uani d . 1 1
H H17A 0.3131 0.0064 0.7278 0.056 Uiso calc R 1 1
H H17B 0.1937 0.1266 0.6384 0.056 Uiso calc R 1 1
H H17C 0.2427 0.1575 0.7718 0.056 Uiso calc R 1 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_site_symmetry_3
_geom_angle
C4 Br1 Br1 2_675 147.64(6)
O2 S1 O3 . 119.77(9)
O2 S1 C1 . 106.40(8)
O3 S1 C1 . 109.32(9)
O2 S1 C11 . 107.59(9)
O3 S1 C11 . 107.93(9)
C1 S1 C11 . 104.85(8)
C8 O1 C7 . 107.07(14)
C8 C1 C2 . 107.66(15)
C8 C1 S1 . 126.61(14)
C2 C1 S1 . 125.66(14)
C7 C2 C3 . 119.23(17)
C7 C2 C1 . 104.64(16)
C3 C2 C1 . 136.13(16)
C4 C3 C2 . 116.18(17)
C4 C3 H3 . 121.9
C2 C3 H3 . 121.9
C3 C4 C5 . 123.76(18)
C3 C4 Br1 . 118.52(14)
C5 C4 Br1 . 117.71(14)
C6 C5 C4 . 120.83(18)
C6 C5 H5 . 119.6
C4 C5 H5 . 119.6
C7 C6 C5 . 114.64(17)
C7 C6 C9 . 122.07(18)
C5 C6 C9 . 123.28(17)
O1 C7 C6 . 124.36(16)
O1 C7 C2 . 110.27(15)
C6 C7 C2 . 125.36(18)
C1 C8 O1 . 110.36(16)
C1 C8 C10 . 134.25(17)
O1 C8 C10 . 115.38(16)
C6 C9 H9A . 109.5
C6 C9 H9B . 109.5
H9A C9 H9B . 109.5
C6 C9 H9C . 109.5
H9A C9 H9C . 109.5
H9B C9 H9C . 109.5
C8 C10 H10A . 109.5
C8 C10 H10B . 109.5
H10A C10 H10B . 109.5
C8 C10 H10C . 109.5
H10A C10 H10C . 109.5
H10B C10 H10C . 109.5
C16 C11 C12 . 120.53(18)
C16 C11 S1 . 120.14(14)
C12 C11 S1 . 119.33(15)
C13 C12 C11 . 119.24(19)
C13 C12 H12 . 120.4
C11 C12 H12 . 120.4
C12 C13 C14 . 121.07(19)
C12 C13 H13 . 119.5
C14 C13 H13 . 119.5
C13 C14 C15 . 118.72(18)
C13 C14 C17 . 119.98(19)
C15 C14 C17 . 121.30(19)
C16 C15 C14 . 121.17(19)
C16 C15 H15 . 119.4
C14 C15 H15 . 119.4
C11 C16 C15 . 119.25(18)
C11 C16 H16 . 120.4
C15 C16 H16 . 120.4
C14 C17 H17A . 109.5
C14 C17 H17B . 109.5
H17A C17 H17B . 109.5
C14 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
Br1 C4 . 1.9023(19)
Br1 Br1 2_675 3.6517(4)
S1 O2 . 1.4343(14)
S1 O3 . 1.4381(14)
S1 C1 . 1.7400(17)
S1 C11 . 1.7618(19)
O1 C8 . 1.368(2)
O1 C7 . 1.380(2)
C1 C8 . 1.358(3)
C1 C2 . 1.446(2)
C2 C7 . 1.391(2)
C2 C3 . 1.395(3)
C3 C4 . 1.381(3)
C3 H3 . 0.9500
C4 C5 . 1.395(3)
C5 C6 . 1.391(3)
C5 H5 . 0.9500
C6 C7 . 1.386(3)
C6 C9 . 1.500(3)
C8 C10 . 1.479(3)
C9 H9A . 0.9800
C9 H9B . 0.9800
C9 H9C . 0.9800
C10 H10A . 0.9800
C10 H10B . 0.9800
C10 H10C . 0.9800
C11 C16 . 1.383(3)
C11 C12 . 1.390(3)
C12 C13 . 1.384(3)
C12 H12 . 0.9500
C13 C14 . 1.385(3)
C13 H13 . 0.9500
C14 C15 . 1.385(3)
C14 C17 . 1.507(3)
C15 C16 . 1.385(3)
C15 H15 . 0.9500
C16 H16 . 0.9500
C17 H17A . 0.9800
C17 H17B . 0.9800
C17 H17C . 0.9800
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
C13 H13 O2 2_666 0.95 2.54 3.330(2) 140.4
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
O2 S1 C1 C8 . 156.87(17)
O3 S1 C1 C8 . 26.20(19)
C11 S1 C1 C8 . -89.30(18)
O2 S1 C1 C2 . -26.54(18)
O3 S1 C1 C2 . -157.20(15)
C11 S1 C1 C2 . 87.29(17)
C8 C1 C2 C7 . 0.1(2)
S1 C1 C2 C7 . -177.03(14)
C8 C1 C2 C3 . 179.6(2)
S1 C1 C2 C3 . 2.5(3)
C7 C2 C3 C4 . 0.8(3)
C1 C2 C3 C4 . -178.64(19)
C2 C3 C4 C5 . -0.5(3)
C2 C3 C4 Br1 . 178.49(13)
Br1 Br1 C4 C3 2_675 70.15(19)
Br1 Br1 C4 C5 2_675 -110.76(15)
C3 C4 C5 C6 . 0.3(3)
Br1 C4 C5 C6 . -178.75(14)
C4 C5 C6 C7 . -0.3(3)
C4 C5 C6 C9 . 178.51(18)
C8 O1 C7 C6 . -178.52(17)
C8 O1 C7 C2 . 0.69(19)
C5 C6 C7 O1 . 179.69(16)
C9 C6 C7 O1 . 0.9(3)
C5 C6 C7 C2 . 0.6(3)
C9 C6 C7 C2 . -178.21(18)
C3 C2 C7 O1 . 179.91(15)
C1 C2 C7 O1 . -0.49(19)
C3 C2 C7 C6 . -0.9(3)
C1 C2 C7 C6 . 178.71(17)
C2 C1 C8 O1 . 0.3(2)
S1 C1 C8 O1 . 177.42(13)
C2 C1 C8 C10 . -178.7(2)
S1 C1 C8 C10 . -1.6(3)
C7 O1 C8 C1 . -0.6(2)
C7 O1 C8 C10 . 178.59(16)
O2 S1 C11 C16 . -139.02(15)
O3 S1 C11 C16 . -8.47(18)
C1 S1 C11 C16 . 107.99(16)
O2 S1 C11 C12 . 40.21(17)
O3 S1 C11 C12 . 170.75(15)
C1 S1 C11 C12 . -72.78(16)
C16 C11 C12 C13 . 0.8(3)
S1 C11 C12 C13 . -178.44(16)
C11 C12 C13 C14 . 0.5(3)
C12 C13 C14 C15 . -1.2(3)
C12 C13 C14 C17 . 178.7(2)
C13 C14 C15 C16 . 0.6(3)
C17 C14 C15 C16 . -179.28(19)
C12 C11 C16 C15 . -1.3(3)
S1 C11 C16 C15 . 177.89(15)
C14 C15 C16 C11 . 0.6(3)
