#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/94/2239483.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_2239483
loop_
_publ_author_name
'Choi, Hong Dae'
'Seo, Pil Ja'
'Lee, Uk'
_publ_section_title
;
 5-Bromo-3-cyclohexylsulfinyl-2,4,6-trimethyl-1-benzofuran
;
_journal_coeditor_code           GG2135
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o310
_journal_paper_doi               10.1107/S1600536814003171
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C17 H21 Br O2 S'
_chemical_formula_moiety         'C17 H21 Br O2 S'
_chemical_formula_sum            'C17 H21 Br O2 S'
_chemical_formula_weight         369.31
_chemical_melting_point_gt       450
_chemical_melting_point_lt       451
_chemical_name_systematic
;
5-Bromo-3-cyclohexylsulfinyl-2,4,6-trimethyl-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                65.839(4)
_cell_angle_beta                 85.795(4)
_cell_angle_gamma                83.394(4)
_cell_formula_units_Z            2
_cell_length_a                   5.9051(4)
_cell_length_b                   11.7060(9)
_cell_length_c                   12.7906(10)
_cell_measurement_reflns_used    6652
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.36
_cell_measurement_theta_min      3.07
_cell_volume                     801.01(11)
_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 0.985
_diffrn_measured_fraction_theta_max 0.985
_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  0.0379
_diffrn_reflns_av_sigmaI/netI    0.0357
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14547
_diffrn_reflns_theta_full        28.46
_diffrn_reflns_theta_max         28.46
_diffrn_reflns_theta_min         3.07
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.698
_exptl_absorpt_correction_T_max  0.5198
_exptl_absorpt_correction_T_min  0.4287
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.28
_refine_diff_density_max         1.282
_refine_diff_density_min         -0.884
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3981
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0378
_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)+(0.0292P)²+1.0109P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0877
_refine_ls_wR_factor_ref         0.0908
_reflns_number_gt                3419
_reflns_number_total             3981
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gg2135sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        801.01(10)
_cod_database_code               2239483
_cod_database_fobs_code          2239483
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 -0.27560(5) 0.86915(3) 0.02612(2) 0.03843(10) Uani d . 1 2
S S1 0.58237(11) 0.47281(6) 0.18104(6) 0.03238(15) Uani d DU 1 2
O O1 0.4834(3) 0.69082(15) 0.35369(15) 0.0281(4) Uani d . 1 2
O O2A 0.8063(4) 0.4118(2) 0.2215(2) 0.0408(6) Uani d PDU 0.863(5) 1
O O2B 0.637(2) 0.5186(11) 0.0592(3) 0.036(3) Uani d PDU 0.137(5) 1
C C1 0.4916(4) 0.5828(2) 0.2422(2) 0.0231(5) Uani d . 1 2
C C2 0.2955(4) 0.6766(2) 0.2109(2) 0.0222(4) Uani d . 1 2
C C3 0.1240(4) 0.7157(2) 0.1289(2) 0.0232(5) Uani d . 1 2
C C4 -0.0359(4) 0.8119(2) 0.1324(2) 0.0264(5) Uani d . 1 2
C C5 -0.0339(4) 0.8713(2) 0.2086(2) 0.0290(5) Uani d . 1 2
C C6 0.1401(4) 0.8330(2) 0.2854(2) 0.0290(5) Uani d . 1 2
H H6 0.1498 0.8709 0.3377 0.035 Uiso calc R 1 2
C C7 0.2994(4) 0.7378(2) 0.2837(2) 0.0246(5) Uani d . 1 2
C C8 0.5969(4) 0.5962(2) 0.3264(2) 0.0273(5) Uani d . 1 2
C C9 0.1167(4) 0.6589(2) 0.0433(2) 0.0292(5) Uani d . 1 2
H H9A -0.0024 0.6006 0.0669 0.044 Uiso calc R 1 2
H H9B 0.2647 0.6131 0.0395 0.044 Uiso calc R 1 2
H H9C 0.0829 0.7257 -0.0323 0.044 Uiso calc R 1 2
C C10 -0.2122(5) 0.9752(2) 0.2065(3) 0.0404(7) Uani d . 1 2
H H10A -0.1816 1.0035 0.2660 0.061 Uiso calc R 1 2
H H10B -0.3633 0.9438 0.2210 0.061 Uiso calc R 1 2
H H10C -0.2078 1.0457 0.1313 0.061 Uiso calc R 1 2
C C11 0.8011(5) 0.5326(3) 0.3952(2) 0.0345(6) Uani d . 1 2
H H11A 0.8868 0.4773 0.3628 0.052 Uiso calc R 1 2
H H11B 0.7535 0.4826 0.4745 0.052 Uiso calc R 1 2
H H11C 0.8980 0.5958 0.3938 0.052 Uiso calc R 1 2
C C12 0.3727(4) 0.3601(2) 0.2543(2) 0.0236(5) Uani d . 1 2
H H12 0.2168 0.4061 0.2405 0.028 Uiso calc R 1 2
C C13 0.4062(5) 0.2963(3) 0.3826(2) 0.0361(6) Uani d . 1 2
H H13A 0.3831 0.3599 0.4157 0.043 Uiso calc R 1 2
H H13B 0.5643 0.2562 0.3976 0.043 Uiso calc R 1 2
C C14 0.2387(6) 0.1967(3) 0.4400(2) 0.0447(7) Uani d . 1 2
H H14A 0.2694 0.1530 0.5228 0.054 Uiso calc R 1 2
H H14B 0.0811 0.2381 0.4320 0.054 Uiso calc R 1 2
C C15 0.2590(6) 0.1012(3) 0.3867(3) 0.0442(7) Uani d . 1 2
H H15A 0.1432 0.0407 0.4226 0.053 Uiso calc R 1 2
H H15B 0.4116 0.0538 0.4016 0.053 Uiso calc R 1 2
C C16 0.2251(5) 0.1658(3) 0.2582(2) 0.0380(6) Uani d . 1 2
H H16A 0.0671 0.2061 0.2437 0.046 Uiso calc R 1 2
H H16B 0.2464 0.1021 0.2251 0.046 Uiso calc R 1 2
C C17 0.3923(5) 0.2649(2) 0.1994(2) 0.0312(5) Uani d . 1 2
H H17A 0.3592 0.3091 0.1169 0.037 Uiso calc R 1 2
H H17B 0.5499 0.2237 0.2064 0.037 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 Br1 2_475 129.48(8)
O2B S1 O2A . 97.6(6)
O2B S1 C1 . 119.2(5)
O2A S1 C1 . 110.03(13)
O2B S1 C12 . 123.9(6)
O2A S1 C12 . 107.98(13)
C1 S1 C12 . 97.78(11)
C7 O1 C8 . 106.35(18)
C8 C1 C2 . 106.9(2)
C8 C1 S1 . 125.76(19)
C2 C1 S1 . 127.31(18)
C7 C2 C3 . 119.2(2)
C7 C2 C1 . 104.7(2)
C3 C2 C1 . 136.1(2)
C4 C3 C2 . 115.2(2)
C4 C3 C9 . 122.7(2)
C2 C3 C9 . 122.1(2)
C3 C4 C5 . 125.2(2)
C3 C4 Br1 . 118.04(19)
C5 C4 Br1 . 116.76(18)
C6 C5 C4 . 117.9(2)
C6 C5 C10 . 120.1(2)
C4 C5 C10 . 122.0(2)
C7 C6 C5 . 117.9(2)
C7 C6 H6 . 121.1
C5 C6 H6 . 121.1
O1 C7 C6 . 124.6(2)
O1 C7 C2 . 110.9(2)
C6 C7 C2 . 124.5(2)
C1 C8 O1 . 111.1(2)
C1 C8 C11 . 134.8(2)
O1 C8 C11 . 114.1(2)
C3 C9 H9A . 109.5
C3 C9 H9B . 109.5
H9A C9 H9B . 109.5
C3 C9 H9C . 109.5
H9A C9 H9C . 109.5
H9B C9 H9C . 109.5
C5 C10 H10A . 109.5
C5 C10 H10B . 109.5
H10A C10 H10B . 109.5
C5 C10 H10C . 109.5
H10A C10 H10C . 109.5
H10B C10 H10C . 109.5
C8 C11 H11A . 109.5
C8 C11 H11B . 109.5
H11A C11 H11B . 109.5
C8 C11 H11C . 109.5
H11A C11 H11C . 109.5
H11B C11 H11C . 109.5
C13 C12 C17 . 111.8(2)
C13 C12 S1 . 112.15(18)
C17 C12 S1 . 107.30(17)
C13 C12 H12 . 108.5
C17 C12 H12 . 108.5
S1 C12 H12 . 108.5
C12 C13 C14 . 110.8(2)
C12 C13 H13A . 109.5
C14 C13 H13A . 109.5
C12 C13 H13B . 109.5
C14 C13 H13B . 109.5
H13A C13 H13B . 108.1
C15 C14 C13 . 111.2(2)
C15 C14 H14A . 109.4
C13 C14 H14A . 109.4
C15 C14 H14B . 109.4
C13 C14 H14B . 109.4
H14A C14 H14B . 108.0
C14 C15 C16 . 110.9(2)
C14 C15 H15A . 109.5
C16 C15 H15A . 109.5
C14 C15 H15B . 109.5
C16 C15 H15B . 109.5
H15A C15 H15B . 108.0
C15 C16 C17 . 111.6(2)
C15 C16 H16A . 109.3
C17 C16 H16A . 109.3
C15 C16 H16B . 109.3
C17 C16 H16B . 109.3
H16A C16 H16B . 108.0
C16 C17 C12 . 110.3(2)
C16 C17 H17A . 109.6
C12 C17 H17A . 109.6
C16 C17 H17B . 109.6
C12 C17 H17B . 109.6
H17A C17 H17B . 108.1
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 Br1 2_475 3.6838(6)
S1 O2B . 1.450(2)
S1 O2A . 1.451(2)
S1 C1 . 1.778(2)
S1 C12 . 1.830(2)
O1 C7 . 1.373(3)
O1 C8 . 1.381(3)
C1 C8 . 1.353(3)
C1 C2 . 1.457(3)
C2 C7 . 1.392(3)
C2 C3 . 1.411(3)
C3 C4 . 1.397(3)
C3 C9 . 1.501(3)
C4 C5 . 1.412(4)
C5 C6 . 1.379(4)
C5 C10 . 1.506(3)
C6 C7 . 1.379(3)
C6 H6 . 0.9500
C8 C11 . 1.482(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 H11A . 0.9800
C11 H11B . 0.9800
C11 H11C . 0.9800
C12 C13 . 1.516(3)
C12 C17 . 1.531(3)
C12 H12 . 1.0000
C13 C14 . 1.528(4)
C13 H13A . 0.9900
C13 H13B . 0.9900
C14 C15 . 1.519(4)
C14 H14A . 0.9900
C14 H14B . 0.9900
C15 C16 . 1.520(4)
C15 H15A . 0.9900
C15 H15B . 0.9900
C16 C17 . 1.526(4)
C16 H16A . 0.9900
C16 H16B . 0.9900
C17 H17A . 0.9900
C17 H17B . 0.9900
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
C12 H12 O2A 1_455 1.00 2.44 3.355(3) 151.2
C11 H11C Cg1 1_655 0.98 2.83 3.547(3) 130.4
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
O2B S1 C1 C8 . -120.2(7)
O2A S1 C1 C8 . -8.9(3)
C12 S1 C1 C8 . 103.5(2)
O2B S1 C1 C2 . 58.4(7)
O2A S1 C1 C2 . 169.7(2)
C12 S1 C1 C2 . -77.8(2)
C8 C1 C2 C7 . -1.3(3)
S1 C1 C2 C7 . 179.92(17)
C8 C1 C2 C3 . 177.1(3)
S1 C1 C2 C3 . -1.7(4)
C7 C2 C3 C4 . -2.7(3)
C1 C2 C3 C4 . 179.2(2)
C7 C2 C3 C9 . 176.6(2)
C1 C2 C3 C9 . -1.6(4)
C2 C3 C4 C5 . 1.1(3)
C9 C3 C4 C5 . -178.1(2)
C2 C3 C4 Br1 . -179.22(16)
C9 C3 C4 Br1 . 1.5(3)
Br1 Br1 C4 C3 2_475 -175.07(14)
Br1 Br1 C4 C5 2_475 4.6(2)
C3 C4 C5 C6 . 0.7(4)
Br1 C4 C5 C6 . -179.00(18)
C3 C4 C5 C10 . 179.6(2)
Br1 C4 C5 C10 . 0.0(3)
C4 C5 C6 C7 . -0.8(3)
C10 C5 C6 C7 . -179.8(2)
C8 O1 C7 C6 . 179.0(2)
C8 O1 C7 C2 . -1.0(3)
C5 C6 C7 O1 . 179.1(2)
C5 C6 C7 C2 . -0.8(4)
C3 C2 C7 O1 . -177.3(2)
C1 C2 C7 O1 . 1.4(3)
C3 C2 C7 C6 . 2.7(4)
C1 C2 C7 C6 . -178.6(2)
C2 C1 C8 O1 . 0.7(3)
S1 C1 C8 O1 . 179.52(16)
C2 C1 C8 C11 . 179.9(3)
S1 C1 C8 C11 . -1.2(4)
C7 O1 C8 C1 . 0.2(3)
C7 O1 C8 C11 . -179.2(2)
O2B S1 C12 C13 . 160.6(7)
O2A S1 C12 C13 . 47.9(2)
C1 S1 C12 C13 . -66.1(2)
O2B S1 C12 C17 . 37.5(7)
O2A S1 C12 C17 . -75.2(2)
C1 S1 C12 C17 . 170.76(17)
C17 C12 C13 C14 . -55.7(3)
S1 C12 C13 C14 . -176.3(2)
C12 C13 C14 C15 . 55.8(4)
C13 C14 C15 C16 . -56.1(4)
C14 C15 C16 C17 . 56.3(4)
C15 C16 C17 C12 . -55.5(3)
C13 C12 C17 C16 . 55.4(3)
S1 C12 C17 C16 . 178.79(19)
