#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/99/2229959.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_2229959
loop_
_publ_author_name
'Choi, Hong Dae'
'Seo, Pil Ja'
'Son, Byeng Wha'
'Lee, Uk'
_publ_section_title
;
 5-Bromo-3-cyclohexylsulfinyl-2,7-dimethyl-1-benzofuran
;
_journal_coeditor_code           DN2669
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1039
_journal_paper_doi               10.1107/S1600536811011354
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C16 H19 Br O2 S'
_chemical_formula_moiety         'C16 H19 Br O2 S'
_chemical_formula_sum            'C16 H19 Br O2 S'
_chemical_formula_weight         355.28
_chemical_name_systematic
;
5-Bromo-3-cyclohexylsulfinyl-2,7-dimethyl-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                104.726(2)
_cell_angle_beta                 101.4260(10)
_cell_angle_gamma                106.3800(10)
_cell_formula_units_Z            2
_cell_length_a                   6.3957(2)
_cell_length_b                   11.2576(3)
_cell_length_c                   12.0384(3)
_cell_measurement_reflns_used    5547
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.05
_cell_measurement_theta_min      3.12
_cell_volume                     769.53(4)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_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      173(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0317
_diffrn_reflns_av_sigmaI/netI    0.0302
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14554
_diffrn_reflns_theta_full        28.55
_diffrn_reflns_theta_max         28.55
_diffrn_reflns_theta_min         1.83
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.805
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6596
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.189
_exptl_crystal_size_mid          0.172
_exptl_crystal_size_min          0.088
_refine_diff_density_max         0.458
_refine_diff_density_min         -0.299
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3887
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0298
_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)+(0.0379P)²+0.1985P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0716
_refine_ls_wR_factor_ref         0.0765
_reflns_number_gt                3165
_reflns_number_total             3887
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2669.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P -1   '
_cod_database_code               2229959
_cod_database_fobs_code          2229959
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 Br1 -0.29117(3) 0.05949(2) 0.42781(2) 0.04566(9) Uani d . 1 . .
S S1 0.59311(8) 0.44037(4) 0.82300(4) 0.02878(11) Uani d . 1 . .
O O1 0.6631(2) 0.39267(13) 0.49722(12) 0.0317(3) Uani d . 1 . .
O O2 0.3652(2) 0.44013(15) 0.83380(13) 0.0419(3) Uani d . 1 . .
C C1 0.5706(3) 0.40074(17) 0.66863(16) 0.0274(4) Uani d . 1 . .
C C2 0.3721(3) 0.31269(17) 0.57099(16) 0.0267(4) Uani d . 1 . .
C C3 0.1515(3) 0.23721(17) 0.56098(17) 0.0292(4) Uani d . 1 . .
H H3 0.0991 0.2367 0.6295 0.035 Uiso calc R 1 . .
C C4 0.0127(3) 0.16314(18) 0.44627(18) 0.0326(4) Uani d . 1 . .
C C5 0.0853(3) 0.16066(19) 0.34375(18) 0.0348(4) Uani d . 1 . .
H H5 -0.0172 0.1066 0.2670 0.042 Uiso calc R 1 . .
C C6 0.3041(3) 0.23572(19) 0.35242(17) 0.0328(4) Uani d . 1 . .
C C7 0.4401(3) 0.31112(18) 0.46765(17) 0.0294(4) Uani d . 1 . .
C C8 0.7373(3) 0.44626(17) 0.62025(17) 0.0291(4) Uani d . 1 . .
C C9 0.3937(4) 0.2351(2) 0.24595(18) 0.0441(5) Uani d . 1 . .
H H9A 0.2719 0.1783 0.1722 0.066 Uiso calc R 1 . .
H H9B 0.5203 0.2021 0.2532 0.066 Uiso calc R 1 . .
H H9C 0.4472 0.3245 0.2430 0.066 Uiso calc R 1 . .
C C10 0.9769(3) 0.53593(19) 0.67278(19) 0.0356(4) Uani d . 1 . .
H H10A 1.0015 0.5858 0.7568 0.053 Uiso calc R 1 . .
H H10B 1.0100 0.5967 0.6276 0.053 Uiso calc R 1 . .
H H10C 1.0781 0.4848 0.6688 0.053 Uiso calc R 1 . .
C C11 0.6185(3) 0.28811(17) 0.84033(16) 0.0272(4) Uani d . 1 . .
H H11 0.4882 0.2124 0.7792 0.033 Uiso calc R 1 . .
C C12 0.6042(5) 0.2884(2) 0.96458(19) 0.0467(5) Uani d . 1 . .
H H12A 0.4538 0.2901 0.9724 0.056 Uiso calc R 1 . .
H H12B 0.7234 0.3675 1.0260 0.056 Uiso calc R 1 . .
C C13 0.6374(6) 0.1651(3) 0.9844(2) 0.0619(7) Uani d . 1 . .
H H13A 0.6342 0.1671 1.0667 0.074 Uiso calc R 1 . .
H H13B 0.5101 0.0867 0.9272 0.074 Uiso calc R 1 . .
C C14 0.8601(5) 0.1549(2) 0.9674(2) 0.0578(7) Uani d . 1 . .
H H14A 0.9883 0.2295 1.0288 0.069 Uiso calc R 1 . .
H H14B 0.8736 0.0728 0.9784 0.069 Uiso calc R 1 . .
C C15 0.8734(4) 0.1555(2) 0.8440(2) 0.0482(6) Uani d . 1 . .
H H15A 0.7550 0.0757 0.7831 0.058 Uiso calc R 1 . .
H H15B 1.0239 0.1537 0.8364 0.058 Uiso calc R 1 . .
C C16 0.8397(4) 0.2765(2) 0.8201(2) 0.0447(5) Uani d . 1 . .
H H16A 0.9689 0.3559 0.8741 0.054 Uiso calc R 1 . .
H H16B 0.8369 0.2704 0.7362 0.054 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C4 Br1 Br1 . 2_456 147.22(6) ?
O2 S1 C1 . . 106.24(8) ?
O2 S1 C11 . . 107.06(9) ?
C1 S1 C11 . . 97.42(8) ?
C8 O1 C7 . . 106.57(14) ?
C8 C1 C2 . . 107.53(16) ?
C8 C1 S1 . . 126.17(14) ?
C2 C1 S1 . . 126.30(14) ?
C3 C2 C7 . . 119.63(17) ?
C3 C2 C1 . . 135.63(18) ?
C7 C2 C1 . . 104.75(16) ?
C4 C3 C2 . . 116.39(18) ?
C4 C3 H3 . . 121.8 ?
C2 C3 H3 . . 121.8 ?
C3 C4 C5 . . 123.19(18) ?
C3 C4 Br1 . . 117.98(15) ?
C5 C4 Br1 . . 118.83(14) ?
C6 C5 C4 . . 120.99(18) ?
C6 C5 H5 . . 119.5 ?
C4 C5 H5 . . 119.5 ?
C7 C6 C5 . . 115.22(18) ?
C7 C6 C9 . . 121.3(2) ?
C5 C6 C9 . . 123.49(19) ?
O1 C7 C6 . . 125.06(17) ?
O1 C7 C2 . . 110.37(16) ?
C6 C7 C2 . . 124.55(18) ?
C1 C8 O1 . . 110.78(16) ?
C1 C8 C10 . . 133.19(18) ?
O1 C8 C10 . . 116.00(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 ?
C12 C11 C16 . . 112.33(17) ?
C12 C11 S1 . . 107.98(13) ?
C16 C11 S1 . . 109.89(13) ?
C12 C11 H11 . . 108.9 ?
C16 C11 H11 . . 108.9 ?
S1 C11 H11 . . 108.9 ?
C11 C12 C13 . . 109.28(18) ?
C11 C12 H12A . . 109.8 ?
C13 C12 H12A . . 109.8 ?
C11 C12 H12B . . 109.8 ?
C13 C12 H12B . . 109.8 ?
H12A C12 H12B . . 108.3 ?
C14 C13 C12 . . 111.7(2) ?
C14 C13 H13A . . 109.3 ?
C12 C13 H13A . . 109.3 ?
C14 C13 H13B . . 109.3 ?
C12 C13 H13B . . 109.3 ?
H13A C13 H13B . . 107.9 ?
C15 C14 C13 . . 110.68(19) ?
C15 C14 H14A . . 109.5 ?
C13 C14 H14A . . 109.5 ?
C15 C14 H14B . . 109.5 ?
C13 C14 H14B . . 109.5 ?
H14A C14 H14B . . 108.1 ?
C14 C15 C16 . . 111.53(19) ?
C14 C15 H15A . . 109.3 ?
C16 C15 H15A . . 109.3 ?
C14 C15 H15B . . 109.3 ?
C16 C15 H15B . . 109.3 ?
H15A C15 H15B . . 108.0 ?
C11 C16 C15 . . 110.72(18) ?
C11 C16 H16A . . 109.5 ?
C15 C16 H16A . . 109.5 ?
C11 C16 H16B . . 109.5 ?
C15 C16 H16B . . 109.5 ?
H16A C16 H16B . . 108.1 ?
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
Br1 C4 . 1.8987(19) ?
Br1 Br1 2_456 3.5994(5) ?
S1 O2 . 1.4885(14) ?
S1 C1 . 1.7634(19) ?
S1 C11 . 1.8259(18) ?
O1 C8 . 1.374(2) ?
O1 C7 . 1.378(2) ?
C1 C8 . 1.352(3) ?
C1 C2 . 1.443(2) ?
C2 C3 . 1.390(3) ?
C2 C7 . 1.395(3) ?
C3 C4 . 1.379(3) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.399(3) ?
C5 C6 . 1.383(3) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.381(3) ?
C6 C9 . 1.503(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 C12 . 1.516(3) ?
C11 C16 . 1.517(3) ?
C11 H11 . 1.0000 ?
C12 C13 . 1.530(3) ?
C12 H12A . 0.9900 ?
C12 H12B . 0.9900 ?
C13 C14 . 1.510(4) ?
C13 H13A . 0.9900 ?
C13 H13B . 0.9900 ?
C14 C15 . 1.507(3) ?
C14 H14A . 0.9900 ?
C14 H14B . 0.9900 ?
C15 C16 . 1.526(3) ?
C15 H15A . 0.9900 ?
C15 H15B . 0.9900 ?
C16 H16A . 0.9900 ?
C16 H16B . 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
C10 H10B Cg1 2_666 0.98 2.97 3.717(2) 134
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 S1 C1 C8 . . . . 146.51(16) ?
C11 S1 C1 C8 . . . . -103.24(17) ?
O2 S1 C1 C2 . . . . -34.29(17) ?
C11 S1 C1 C2 . . . . 75.95(16) ?
C8 C1 C2 C3 . . . . -179.44(19) ?
S1 C1 C2 C3 . . . . 1.2(3) ?
C8 C1 C2 C7 . . . . 0.88(19) ?
S1 C1 C2 C7 . . . . -178.44(13) ?
C7 C2 C3 C4 . . . . 0.6(2) ?
C1 C2 C3 C4 . . . . -179.02(18) ?
C2 C3 C4 C5 . . . . 0.7(3) ?
C2 C3 C4 Br1 . . . . -179.46(12) ?
Br1 Br1 C4 C3 2_456 . . . -6.1(2) ?
Br1 Br1 C4 C5 2_456 . . . 173.74(9) ?
C3 C4 C5 C6 . . . . -1.0(3) ?
Br1 C4 C5 C6 . . . . 179.16(14) ?
C4 C5 C6 C7 . . . . -0.1(3) ?
C4 C5 C6 C9 . . . . 178.64(18) ?
C8 O1 C7 C6 . . . . -178.41(17) ?
C8 O1 C7 C2 . . . . 0.08(19) ?
C5 C6 C7 O1 . . . . 179.78(16) ?
C9 C6 C7 O1 . . . . 1.0(3) ?
C5 C6 C7 C2 . . . . 1.5(3) ?
C9 C6 C7 C2 . . . . -177.25(17) ?
C3 C2 C7 O1 . . . . 179.67(15) ?
C1 C2 C7 O1 . . . . -0.58(19) ?
C3 C2 C7 C6 . . . . -1.8(3) ?
C1 C2 C7 C6 . . . . 177.92(17) ?
C2 C1 C8 O1 . . . . -0.9(2) ?
S1 C1 C8 O1 . . . . 178.45(12) ?
C2 C1 C8 C10 . . . . -178.65(19) ?
S1 C1 C8 C10 . . . . 0.7(3) ?
C7 O1 C8 C1 . . . . 0.51(19) ?
C7 O1 C8 C10 . . . . 178.71(15) ?
O2 S1 C11 C12 . . . . -61.81(16) ?
C1 S1 C11 C12 . . . . -171.38(15) ?
O2 S1 C11 C16 . . . . 175.35(14) ?
C1 S1 C11 C16 . . . . 65.79(15) ?
C16 C11 C12 C13 . . . . -55.8(3) ?
S1 C11 C12 C13 . . . . -177.09(19) ?
C11 C12 C13 C14 . . . . 56.7(3) ?
C12 C13 C14 C15 . . . . -57.4(3) ?
C13 C14 C15 C16 . . . . 55.9(3) ?
C12 C11 C16 C15 . . . . 55.2(2) ?
S1 C11 C16 C15 . . . . 175.44(16) ?
C14 C15 C16 C11 . . . . -54.6(3) ?
