#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/93/2239342.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_2239342
loop_
_publ_author_name
'Choi, Hong Dae'
'Seo, Pil Ja'
'Lee, Uk'
_publ_section_title
;
 5-Bromo-2,7-dimethyl-3-(3-methylphenylsulfonyl)-1-benzofuran
;
_journal_coeditor_code           BH2497
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o567
_journal_paper_doi               10.1107/S1600536814008149
_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       439
_chemical_melting_point_lt       438
_chemical_name_systematic
;
5-Bromo-2,7-dimethyl-3-(3-methylphenylsulfonyl)-1-benzofuran
;
_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_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'form.cif (version 2.0)'
_cell_angle_alpha                90.00
_cell_angle_beta                 97.6350(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.8813(3)
_cell_length_b                   6.5976(2)
_cell_length_c                   26.5044(8)
_cell_measurement_reflns_used    9774
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.24
_cell_measurement_theta_min      2.31
_cell_volume                     1539.26(8)
_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      296(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0434
_diffrn_reflns_av_sigmaI/netI    0.0289
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            26392
_diffrn_reflns_theta_full        28.33
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         1.55
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.815
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.3794
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.637
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.555
_refine_diff_density_min         -0.445
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3831
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0307
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0364P)²+0.7777P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0746
_refine_ls_wR_factor_ref         0.0805
_reflns_number_gt                3188
_reflns_number_total             3831
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bh2497sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2239342
_cod_database_fobs_code          2239342
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
_atom_site_symmetry_multiplicity
Br Br1 0.46068(3) 0.80654(4) 0.428686(8) 0.04118(9) Uani d . 1 2
S S1 0.26202(5) 0.72154(8) 0.641971(18) 0.02783(11) Uani d . 1 2
O O1 0.09711(16) 0.2852(2) 0.55049(5) 0.0314(3) Uani d . 1 2
O O2 0.27849(16) 0.9169(2) 0.61959(5) 0.0352(3) Uani d . 1 2
O O3 0.16243(16) 0.7009(3) 0.68033(6) 0.0380(4) Uani d . 1 2
C C1 0.2041(2) 0.5514(3) 0.59334(7) 0.0284(4) Uani d . 1 2
C C2 0.2454(2) 0.5613(3) 0.54261(7) 0.0277(4) Uani d . 1 2
C C3 0.3313(2) 0.6908(3) 0.51640(7) 0.0305(4) Uani d . 1 2
H H3 0.3777 0.8062 0.5314 0.037 Uiso calc R 1 2
C C4 0.3435(2) 0.6375(4) 0.46673(7) 0.0318(4) Uani d . 1 2
C C5 0.2756(2) 0.4660(4) 0.44286(7) 0.0347(5) Uani d . 1 2
H H5 0.2888 0.4380 0.4093 0.042 Uiso calc R 1 2
C C6 0.1884(2) 0.3360(3) 0.46849(8) 0.0325(4) Uani d . 1 2
C C7 0.1763(2) 0.3932(3) 0.51806(7) 0.0291(4) Uani d . 1 2
C C8 0.1157(2) 0.3850(3) 0.59611(7) 0.0302(4) Uani d . 1 2
C C9 0.1153(3) 0.1474(4) 0.44553(8) 0.0415(5) Uani d . 1 2
H H9A 0.1709 0.0312 0.4596 0.062 Uiso calc R 1 2
H H9B 0.1157 0.1499 0.4093 0.062 Uiso calc R 1 2
H H9C 0.0125 0.1399 0.4529 0.062 Uiso calc R 1 2
C C10 0.0370(3) 0.2911(3) 0.63612(9) 0.0368(5) Uani d . 1 2
H H10A 0.0463 0.3777 0.6655 0.055 Uiso calc R 1 2
H H10B 0.0821 0.1619 0.6454 0.055 Uiso calc R 1 2
H H10C -0.0685 0.2730 0.6235 0.055 Uiso calc R 1 2
C C11 0.4444(2) 0.6401(3) 0.66941(7) 0.0283(4) Uani d . 1 2
C C12 0.5609(2) 0.7803(3) 0.67428(7) 0.0314(4) Uani d . 1 2
H H12 0.5452 0.9090 0.6603 0.038 Uiso calc R 1 2
C C13 0.7026(2) 0.7273(4) 0.70039(8) 0.0389(5) Uani d . 1 2
C C14 0.7213(3) 0.5329(4) 0.71966(8) 0.0461(6) Uani d . 1 2
H H14 0.8152 0.4950 0.7369 0.055 Uiso calc R 1 2
C C15 0.6045(3) 0.3937(4) 0.71410(8) 0.0444(6) Uani d . 1 2
H H15 0.6208 0.2638 0.7274 0.053 Uiso calc R 1 2
C C16 0.4631(2) 0.4458(4) 0.68888(8) 0.0367(5) Uani d . 1 2
H H16 0.3834 0.3533 0.6852 0.044 Uiso calc R 1 2
C C17 0.8290(2) 0.8819(5) 0.70728(10) 0.0535(7) Uani d . 1 2
H H17A 0.8362 0.9388 0.7409 0.080 Uiso calc R 1 2
H H17B 0.8078 0.9877 0.6825 0.080 Uiso calc R 1 2
H H17C 0.9233 0.8176 0.7029 0.080 Uiso calc R 1 2
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 O2 3_676 168.67(6)
O2 S1 O3 . 118.89(9)
O2 S1 C1 . 108.10(9)
O3 S1 C1 . 108.30(10)
O2 S1 C11 . 107.76(10)
O3 S1 C11 . 107.20(9)
C1 S1 C11 . 105.88(9)
C8 O1 C7 . 106.91(16)
C8 C1 C2 . 107.93(17)
C8 C1 S1 . 126.84(15)
C2 C1 S1 . 125.22(16)
C7 C2 C3 . 119.64(18)
C7 C2 C1 . 104.47(18)
C3 C2 C1 . 135.88(19)
C4 C3 C2 . 115.9(2)
C4 C3 H3 . 122.0
C2 C3 H3 . 122.0
C3 C4 C5 . 123.7(2)
C3 C4 Br1 . 118.26(17)
C5 C4 Br1 . 117.99(15)
C6 C5 C4 . 120.94(18)
C6 C5 H5 . 119.5
C4 C5 H5 . 119.5
C7 C6 C5 . 114.4(2)
C7 C6 C9 . 122.0(2)
C5 C6 C9 . 123.63(19)
O1 C7 C6 . 124.08(19)
O1 C7 C2 . 110.57(16)
C6 C7 C2 . 125.3(2)
C1 C8 O1 . 110.12(17)
C1 C8 C10 . 135.10(19)
O1 C8 C10 . 114.78(19)
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
C12 C11 C16 . 122.29(19)
C12 C11 S1 . 117.95(16)
C16 C11 S1 . 119.54(17)
C11 C12 C13 . 119.5(2)
C11 C12 H12 . 120.2
C13 C12 H12 . 120.2
C14 C13 C12 . 118.1(2)
C14 C13 C17 . 122.1(2)
C12 C13 C17 . 119.8(2)
C15 C14 C13 . 121.8(2)
C15 C14 H14 . 119.1
C13 C14 H14 . 119.1
C14 C15 C16 . 120.5(2)
C14 C15 H15 . 119.8
C16 C15 H15 . 119.8
C11 C16 C15 . 117.8(2)
C11 C16 H16 . 121.1
C15 C16 H16 . 121.1
C13 C17 H17A . 109.5
C13 C17 H17B . 109.5
H17A C17 H17B . 109.5
C13 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 . 1.903(2)
Br1 O2 3_676 3.3350(16)
S1 O2 . 1.4341(17)
S1 O3 . 1.4400(15)
S1 C1 . 1.735(2)
S1 C11 . 1.7687(19)
O1 C8 . 1.368(2)
O1 C7 . 1.379(3)
C1 C8 . 1.358(3)
C1 C2 . 1.441(3)
C2 C7 . 1.387(3)
C2 C3 . 1.391(3)
C3 C4 . 1.381(3)
C3 H3 . 0.9300
C4 C5 . 1.394(3)
C5 C6 . 1.392(3)
C5 H5 . 0.9300
C6 C7 . 1.385(3)
C6 C9 . 1.495(3)
C8 C10 . 1.481(3)
C9 H9A . 0.9600
C9 H9B . 0.9600
C9 H9C . 0.9600
C10 H10A . 0.9600
C10 H10B . 0.9600
C10 H10C . 0.9600
C11 C12 . 1.381(3)
C11 C16 . 1.383(3)
C12 C13 . 1.398(3)
C12 H12 . 0.9300
C13 C14 . 1.382(4)
C13 C17 . 1.510(4)
C14 C15 . 1.379(4)
C14 H14 . 0.9300
C15 C16 . 1.385(3)
C15 H15 . 0.9300
C16 H16 . 0.9300
C17 H17A . 0.9600
C17 H17B . 0.9600
C17 H17C . 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
C10 H10B O2 1_545 0.96 2.54 3.338(3) 140.9
C17 H17C O3 1_655 0.96 2.41 3.357(3) 169.8
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 . -149.32(17)
O3 S1 C1 C8 . -19.3(2)
C11 S1 C1 C8 . 95.42(18)
O2 S1 C1 C2 . 32.05(18)
O3 S1 C1 C2 . 162.10(16)
C11 S1 C1 C2 . -83.20(18)
C8 C1 C2 C7 . -0.2(2)
S1 C1 C2 C7 . 178.62(14)
C8 C1 C2 C3 . 180.0(2)
S1 C1 C2 C3 . -1.2(3)
C7 C2 C3 C4 . -1.2(3)
C1 C2 C3 C4 . 178.6(2)
C2 C3 C4 C5 . 0.1(3)
C2 C3 C4 Br1 . -179.53(13)
O2 Br1 C4 C3 3_676 58.1(4)
O2 Br1 C4 C5 3_676 -121.5(3)
C3 C4 C5 C6 . 0.4(3)
Br1 C4 C5 C6 . -179.97(15)
C4 C5 C6 C7 . 0.2(3)
C4 C5 C6 C9 . -178.61(19)
C8 O1 C7 C6 . 177.97(18)
C8 O1 C7 C2 . 0.0(2)
C5 C6 C7 O1 . -179.12(17)
C9 C6 C7 O1 . -0.3(3)
C5 C6 C7 C2 . -1.5(3)
C9 C6 C7 C2 . 177.39(19)
C3 C2 C7 O1 . 179.96(16)
C1 C2 C7 O1 . 0.1(2)
C3 C2 C7 C6 . 2.0(3)
C1 C2 C7 C6 . -177.80(18)
C2 C1 C8 O1 . 0.2(2)
S1 C1 C8 O1 . -178.57(14)
C2 C1 C8 C10 . -179.5(2)
S1 C1 C8 C10 . 1.7(3)
C7 O1 C8 C1 . -0.2(2)
C7 O1 C8 C10 . 179.60(16)
O2 S1 C11 C12 . 12.15(17)
O3 S1 C11 C12 . -116.91(15)
C1 S1 C11 C12 . 127.64(16)
O2 S1 C11 C16 . -173.10(15)
O3 S1 C11 C16 . 57.84(18)
C1 S1 C11 C16 . -57.62(18)
C16 C11 C12 C13 . -1.1(3)
S1 C11 C12 C13 . 173.54(15)
C11 C12 C13 C14 . 1.2(3)
C11 C12 C13 C17 . -178.06(19)
C12 C13 C14 C15 . -0.6(3)
C17 C13 C14 C15 . 178.7(2)
C13 C14 C15 C16 . -0.3(3)
C12 C11 C16 C15 . 0.2(3)
S1 C11 C16 C15 . -174.34(15)
C14 C15 C16 C11 . 0.5(3)
