#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/04/2230406.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_2230406
loop_
_publ_author_name
'Seo, Pil Ja'
'Choi, Hong Dae'
'Son, Byeng Wha'
'Lee, Uk'
_publ_section_title
;
 5-Cyclohexyl-2-methyl-3-phenylsulfonyl-1-benzofuran
;
_journal_coeditor_code           LD2013
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1496
_journal_paper_doi               10.1107/S1600536811018903
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C21 H22 O3 S'
_chemical_formula_moiety         'C21 H22 O3 S'
_chemical_formula_sum            'C21 H22 O3 S'
_chemical_formula_weight         354.45
_chemical_name_systematic
;
5-Cyclohexyl-2-methyl-3-phenylsulfonyl-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                90.689(2)
_cell_angle_beta                 109.4700(10)
_cell_angle_gamma                95.634(2)
_cell_formula_units_Z            2
_cell_length_a                   9.0424(2)
_cell_length_b                   10.1585(3)
_cell_length_c                   10.3451(3)
_cell_measurement_reflns_used    6655
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.12
_cell_measurement_theta_min      2.40
_cell_volume                     890.59(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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD'
_diffrn_measurement_method       'φ and ω'
_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  0.0307
_diffrn_reflns_av_sigmaI/netI    0.0278
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15432
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.02
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6824
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.336
_exptl_crystal_size_mid          0.225
_exptl_crystal_size_min          0.176
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.447
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3899
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0406
_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)+(0.0509P)²+0.3567P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1083
_reflns_number_gt                3309
_reflns_number_total             3899
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ld2013.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P -1   '
_cod_database_code               2230406
_cod_database_fobs_code          2230406
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.35282(4) 0.02944(4) 0.20427(4) 0.02763(12) Uani d . 1 2 . .
O O1 0.52551(14) 0.33013(12) 0.04563(12) 0.0356(3) Uani d . 1 2 . .
O O2 0.26982(14) -0.04640(12) 0.07882(12) 0.0372(3) Uani d . 1 2 . .
O O3 0.46616(13) -0.03055(11) 0.31344(12) 0.0353(3) Uani d . 1 2 . .
C C1 0.44833(18) 0.17184(16) 0.16487(16) 0.0280(3) Uani d . 1 2 . .
C C2 0.55947(17) 0.26784(15) 0.26329(16) 0.0273(3) Uani d . 1 2 . .
C C3 0.62369(17) 0.28344(15) 0.40582(16) 0.0273(3) Uani d . 1 2 . .
H H3 0.5958 0.2194 0.4622 0.033 Uiso calc R 1 2 . .
C C4 0.72944(18) 0.39460(16) 0.46415(17) 0.0293(3) Uani d . 1 2 . .
C C5 0.7685(2) 0.48740(17) 0.37830(19) 0.0357(4) Uani d . 1 2 . .
H H5 0.8407 0.5629 0.4190 0.043 Uiso calc R 1 2 . .
C C6 0.7061(2) 0.47346(18) 0.23670(19) 0.0381(4) Uani d . 1 2 . .
H H6 0.7334 0.5370 0.1796 0.046 Uiso calc R 1 2 . .
C C7 0.60245(19) 0.36255(17) 0.18333(17) 0.0314(4) Uani d . 1 2 . .
C C8 0.43211(19) 0.21380(17) 0.03673(17) 0.0318(4) Uani d . 1 2 . .
C C9 0.79944(18) 0.41842(16) 0.61788(17) 0.0302(3) Uani d . 1 2 . .
H H9 0.8891 0.4900 0.6367 0.036 Uiso calc R 1 2 . .
C C10 0.6804(2) 0.4677(2) 0.67798(19) 0.0441(5) Uani d . 1 2 . .
H H10A 0.6430 0.5497 0.6335 0.053 Uiso calc R 1 2 . .
H H10B 0.5881 0.4001 0.6582 0.053 Uiso calc R 1 2 . .
C C11 0.7530(2) 0.4957(2) 0.83250(19) 0.0461(5) Uani d . 1 2 . .
H H11A 0.8386 0.5695 0.8518 0.055 Uiso calc R 1 2 . .
H H11B 0.6717 0.5232 0.8686 0.055 Uiso calc R 1 2 . .
C C12 0.8189(2) 0.37507(19) 0.90467(18) 0.0385(4) Uani d . 1 2 . .
H H12A 0.7314 0.3045 0.8942 0.046 Uiso calc R 1 2 . .
H H12B 0.8710 0.3980 1.0039 0.046 Uiso calc R 1 2 . .
C C13 0.9367(2) 0.32409(17) 0.84674(17) 0.0349(4) Uani d . 1 2 . .
H H13A 0.9716 0.2415 0.8912 0.042 Uiso calc R 1 2 . .
H H13B 1.0305 0.3903 0.8678 0.042 Uiso calc R 1 2 . .
C C14 0.8662(2) 0.29686(17) 0.69219(17) 0.0332(4) Uani d . 1 2 . .
H H14A 0.7810 0.2227 0.6720 0.040 Uiso calc R 1 2 . .
H H14B 0.9486 0.2697 0.6572 0.040 Uiso calc R 1 2 . .
C C15 0.3387(2) 0.1631(2) -0.10457(17) 0.0412(4) Uani d . 1 2 . .
H H15A 0.3062 0.0683 -0.1041 0.062 Uiso calc R 1 2 . .
H H15B 0.4030 0.1771 -0.1639 0.062 Uiso calc R 1 2 . .
H H15C 0.2449 0.2104 -0.1393 0.062 Uiso calc R 1 2 . .
C C16 0.21258(18) 0.08522(15) 0.27032(16) 0.0269(3) Uani d . 1 2 . .
C C17 0.06959(19) 0.11585(17) 0.17967(17) 0.0347(4) Uani d . 1 2 . .
H H17 0.0482 0.1080 0.0834 0.042 Uiso calc R 1 2 . .
C C18 -0.0408(2) 0.1578(2) 0.2310(2) 0.0434(4) Uani d . 1 2 . .
H H18 -0.1388 0.1796 0.1700 0.052 Uiso calc R 1 2 . .
C C19 -0.0097(2) 0.1683(2) 0.3705(2) 0.0471(5) Uani d . 1 2 . .
H H19 -0.0865 0.1968 0.4055 0.057 Uiso calc R 1 2 . .
C C20 0.1332(2) 0.1373(2) 0.45998(19) 0.0464(5) Uani d . 1 2 . .
H H20 0.1539 0.1449 0.5562 0.056 Uiso calc R 1 2 . .
C C21 0.2459(2) 0.09552(18) 0.41083(17) 0.0355(4) Uani d . 1 2 . .
H H21 0.3441 0.0743 0.4721 0.043 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'
S S 0.1246 0.1234 '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'
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
O2 S1 O3 . . 119.24(7) ?
O2 S1 C1 . . 108.08(8) ?
O3 S1 C1 . . 107.73(7) ?
O2 S1 C16 . . 108.19(7) ?
O3 S1 C16 . . 107.58(7) ?
C1 S1 C16 . . 105.18(7) ?
C8 O1 C7 . . 107.18(12) ?
C8 C1 C2 . . 107.85(14) ?
C8 C1 S1 . . 126.38(13) ?
C2 C1 S1 . . 125.77(12) ?
C7 C2 C3 . . 119.42(15) ?
C7 C2 C1 . . 104.35(14) ?
C3 C2 C1 . . 136.23(15) ?
C4 C3 C2 . . 118.86(15) ?
C4 C3 H3 . . 120.6 ?
C2 C3 H3 . . 120.6 ?
C3 C4 C5 . . 119.30(15) ?
C3 C4 C9 . . 121.16(14) ?
C5 C4 C9 . . 119.53(15) ?
C6 C5 C4 . . 122.64(16) ?
C6 C5 H5 . . 118.7 ?
C4 C5 H5 . . 118.7 ?
C7 C6 C5 . . 116.24(16) ?
C7 C6 H6 . . 121.9 ?
C5 C6 H6 . . 121.9 ?
C6 C7 O1 . . 125.78(15) ?
C6 C7 C2 . . 123.55(16) ?
O1 C7 C2 . . 110.67(14) ?
C1 C8 O1 . . 109.95(15) ?
C1 C8 C15 . . 134.96(17) ?
O1 C8 C15 . . 115.09(14) ?
C4 C9 C14 . . 113.14(13) ?
C4 C9 C10 . . 111.63(13) ?
C14 C9 C10 . . 109.87(14) ?
C4 C9 H9 . . 107.3 ?
C14 C9 H9 . . 107.3 ?
C10 C9 H9 . . 107.3 ?
C11 C10 C9 . . 111.47(14) ?
C11 C10 H10A . . 109.3 ?
C9 C10 H10A . . 109.3 ?
C11 C10 H10B . . 109.3 ?
C9 C10 H10B . . 109.3 ?
H10A C10 H10B . . 108.0 ?
C12 C11 C10 . . 111.40(15) ?
C12 C11 H11A . . 109.3 ?
C10 C11 H11A . . 109.3 ?
C12 C11 H11B . . 109.3 ?
C10 C11 H11B . . 109.3 ?
H11A C11 H11B . . 108.0 ?
C11 C12 C13 . . 111.29(15) ?
C11 C12 H12A . . 109.4 ?
C13 C12 H12A . . 109.4 ?
C11 C12 H12B . . 109.4 ?
C13 C12 H12B . . 109.4 ?
H12A C12 H12B . . 108.0 ?
C12 C13 C14 . . 111.59(14) ?
C12 C13 H13A . . 109.3 ?
C14 C13 H13A . . 109.3 ?
C12 C13 H13B . . 109.3 ?
C14 C13 H13B . . 109.3 ?
H13A C13 H13B . . 108.0 ?
C13 C14 C9 . . 111.94(14) ?
C13 C14 H14A . . 109.2 ?
C9 C14 H14A . . 109.2 ?
C13 C14 H14B . . 109.2 ?
C9 C14 H14B . . 109.2 ?
H14A C14 H14B . . 107.9 ?
C8 C15 H15A . . 109.5 ?
C8 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C8 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C21 C16 C17 . . 121.39(16) ?
C21 C16 S1 . . 119.54(12) ?
C17 C16 S1 . . 119.06(13) ?
C18 C17 C16 . . 119.13(16) ?
C18 C17 H17 . . 120.4 ?
C16 C17 H17 . . 120.4 ?
C17 C18 C19 . . 120.22(16) ?
C17 C18 H18 . . 119.9 ?
C19 C18 H18 . . 119.9 ?
C18 C19 C20 . . 120.16(18) ?
C18 C19 H19 . . 119.9 ?
C20 C19 H19 . . 119.9 ?
C21 C20 C19 . . 120.64(17) ?
C21 C20 H20 . . 119.7 ?
C19 C20 H20 . . 119.7 ?
C20 C21 C16 . . 118.46(16) ?
C20 C21 H21 . . 120.8 ?
C16 C21 H21 . . 120.8 ?
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
S1 O2 . 1.4333(12) ?
S1 O3 . 1.4370(11) ?
S1 C1 . 1.7344(16) ?
S1 C16 . 1.7622(16) ?
O1 C8 . 1.367(2) ?
O1 C7 . 1.380(2) ?
C1 C8 . 1.363(2) ?
C1 C2 . 1.449(2) ?
C2 C7 . 1.386(2) ?
C2 C3 . 1.394(2) ?
C3 C4 . 1.393(2) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.402(2) ?
C4 C9 . 1.509(2) ?
C5 C6 . 1.383(3) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.373(2) ?
C6 H6 . 0.9500 ?
C8 C15 . 1.479(2) ?
C9 C14 . 1.530(2) ?
C9 C10 . 1.530(2) ?
C9 H9 . 1.0000 ?
C10 C11 . 1.523(2) ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C11 C12 . 1.510(3) ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C12 C13 . 1.513(2) ?
C12 H12A . 0.9900 ?
C12 H12B . 0.9900 ?
C13 C14 . 1.521(2) ?
C13 H13A . 0.9900 ?
C13 H13B . 0.9900 ?
C14 H14A . 0.9900 ?
C14 H14B . 0.9900 ?
C15 H15A . 0.9800 ?
C15 H15B . 0.9800 ?
C15 H15C . 0.9800 ?
C16 C21 . 1.383(2) ?
C16 C17 . 1.388(2) ?
C17 C18 . 1.375(3) ?
C17 H17 . 0.9500 ?
C18 C19 . 1.376(3) ?
C18 H18 . 0.9500 ?
C19 C20 . 1.384(3) ?
C19 H19 . 0.9500 ?
C20 C21 . 1.379(3) ?
C20 H20 . 0.9500 ?
C21 H21 . 0.9500 ?
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
C21 H21 O3 2_656 0.95 2.39 3.284(2) 157
C11 H11B Cg 2_666 0.99 2.81 3.632(2) 142
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 . . . . 7.74(17) ?
O3 S1 C1 C8 . . . . 137.82(14) ?
C16 S1 C1 C8 . . . . -107.65(15) ?
O2 S1 C1 C2 . . . . -172.58(12) ?
O3 S1 C1 C2 . . . . -42.50(15) ?
C16 S1 C1 C2 . . . . 72.03(14) ?
C8 C1 C2 C7 . . . . -0.12(17) ?
S1 C1 C2 C7 . . . . -179.85(12) ?
C8 C1 C2 C3 . . . . 179.19(17) ?
S1 C1 C2 C3 . . . . -0.5(3) ?
C7 C2 C3 C4 . . . . 0.2(2) ?
C1 C2 C3 C4 . . . . -179.04(16) ?
C2 C3 C4 C5 . . . . -0.1(2) ?
C2 C3 C4 C9 . . . . 178.41(13) ?
C3 C4 C5 C6 . . . . 0.0(2) ?
C9 C4 C5 C6 . . . . -178.53(15) ?
C4 C5 C6 C7 . . . . 0.0(3) ?
C5 C6 C7 O1 . . . . 179.21(15) ?
C5 C6 C7 C2 . . . . 0.2(3) ?
C8 O1 C7 C6 . . . . -179.08(16) ?
C8 O1 C7 C2 . . . . 0.08(17) ?
C3 C2 C7 C6 . . . . -0.3(2) ?
C1 C2 C7 C6 . . . . 179.20(15) ?
C3 C2 C7 O1 . . . . -179.43(13) ?
C1 C2 C7 O1 . . . . 0.03(17) ?
C2 C1 C8 O1 . . . . 0.18(18) ?
S1 C1 C8 O1 . . . . 179.90(11) ?
C2 C1 C8 C15 . . . . -179.60(18) ?
S1 C1 C8 C15 . . . . 0.1(3) ?
C7 O1 C8 C1 . . . . -0.16(17) ?
C7 O1 C8 C15 . . . . 179.66(13) ?
C3 C4 C9 C14 . . . . 48.8(2) ?
C5 C4 C9 C14 . . . . -132.76(16) ?
C3 C4 C9 C10 . . . . -75.79(19) ?
C5 C4 C9 C10 . . . . 102.70(18) ?
C4 C9 C10 C11 . . . . -178.26(15) ?
C14 C9 C10 C11 . . . . 55.4(2) ?
C9 C10 C11 C12 . . . . -56.4(2) ?
C10 C11 C12 C13 . . . . 55.5(2) ?
C11 C12 C13 C14 . . . . -54.8(2) ?
C12 C13 C14 C9 . . . . 55.05(19) ?
C4 C9 C14 C13 . . . . 179.67(13) ?
C10 C9 C14 C13 . . . . -54.83(18) ?
O2 S1 C16 C21 . . . . 145.40(14) ?
O3 S1 C16 C21 . . . . 15.35(15) ?
C1 S1 C16 C21 . . . . -99.29(14) ?
O2 S1 C16 C17 . . . . -33.55(15) ?
O3 S1 C16 C17 . . . . -163.60(13) ?
C1 S1 C16 C17 . . . . 81.76(14) ?
C21 C16 C17 C18 . . . . 0.2(3) ?
S1 C16 C17 C18 . . . . 179.18(14) ?
C16 C17 C18 C19 . . . . -0.4(3) ?
C17 C18 C19 C20 . . . . 0.3(3) ?
C18 C19 C20 C21 . . . . -0.1(3) ?
C19 C20 C21 C16 . . . . -0.1(3) ?
C17 C16 C21 C20 . . . . 0.0(3) ?
S1 C16 C21 C20 . . . . -178.94(14) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656716
