#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/98/2229898.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_2229898
loop_
_publ_author_name
'Choi, Hong Dae'
'Seo, Pil Ja'
'Son, Byeng Wha'
'Lee, Uk'
_publ_section_title
;
 5-Cyclohexyl-3-(4-fluorophenylsulfinyl)-2-methyl-1-benzofuran
;
_journal_coeditor_code           ZQ2090
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o768
_journal_paper_doi               10.1107/S1600536811007112
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C21 H21 F O2 S'
_chemical_formula_moiety         'C21 H21 F O2 S'
_chemical_formula_sum            'C21 H21 F O2 S'
_chemical_formula_weight         356.44
_chemical_name_systematic
;
5-Cyclohexyl-3-(4-fluorophenylsulfinyl)-2-methyl-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                81.1270(10)
_cell_angle_beta                 66.7160(10)
_cell_angle_gamma                72.2480(10)
_cell_formula_units_Z            2
_cell_length_a                   9.2531(2)
_cell_length_b                   10.1934(2)
_cell_length_c                   10.8151(2)
_cell_measurement_reflns_used    6765
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.33
_cell_measurement_theta_min      2.57
_cell_volume                     891.73(3)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0268
_diffrn_reflns_av_sigmaI/netI    0.0250
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15790
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         2.05
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_T_max  0.9643
_exptl_absorpt_correction_T_min  0.9428
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.599
_refine_diff_density_min         -0.273
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         4073
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0400
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0539P)²+0.3464P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1108
_reflns_number_gt                3436
_reflns_number_total             4073
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zq2090.cif
_cod_data_source_block           I
_cod_database_code               2229898
_cod_database_fobs_code          2229898
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
S S1 0.16989(5) 0.52226(4) 0.70879(4) 0.03038(12) Uani d . 1 . .
F F1 0.60813(14) 0.09572(12) 0.92500(12) 0.0523(3) Uani d . 1 . .
O O1 -0.06925(13) 0.32462(11) 0.60921(11) 0.0329(3) Uani d . 1 . .
O O2 0.27322(16) 0.59605(12) 0.59571(12) 0.0426(3) Uani d . 1 . .
C C1 0.10554(18) 0.41527(15) 0.64093(14) 0.0273(3) Uani d . 1 . .
C C2 0.19912(18) 0.32226(15) 0.53060(14) 0.0264(3) Uani d . 1 . .
C C3 0.36263(18) 0.27915(15) 0.44540(14) 0.0280(3) Uani d . 1 . .
H H3 0.4427 0.3139 0.4534 0.034 Uiso calc R 1 . .
C C4 0.40637(19) 0.18409(15) 0.34828(15) 0.0298(3) Uani d . 1 . .
C C5 0.2851(2) 0.13569(17) 0.33787(16) 0.0355(4) Uani d . 1 . .
H H5 0.3163 0.0712 0.2711 0.043 Uiso calc R 1 . .
C C6 0.1226(2) 0.17765(18) 0.42034(16) 0.0361(4) Uani d . 1 . .
H H6 0.0417 0.1445 0.4118 0.043 Uiso calc R 1 . .
C C7 0.08481(18) 0.27058(16) 0.51576(15) 0.0293(3) Uani d . 1 . .
C C8 -0.05259(18) 0.41298(16) 0.68288(15) 0.0299(3) Uani d . 1 . .
C C9 0.5826(2) 0.13384(16) 0.25508(15) 0.0321(3) Uani d . 1 . .
H H9 0.5877 0.0668 0.1940 0.038 Uiso calc R 1 . .
C C10 0.6938(2) 0.05807(19) 0.33242(18) 0.0459(5) Uani d . 1 . .
H H10A 0.6882 0.1212 0.3961 0.055 Uiso calc R 1 . .
H H10B 0.6547 -0.0210 0.3854 0.055 Uiso calc R 1 . .
C C11 0.8704(2) 0.00624(19) 0.23672(18) 0.0466(5) Uani d . 1 . .
H H11A 0.9398 -0.0392 0.2896 0.056 Uiso calc R 1 . .
H H11B 0.8775 -0.0630 0.1781 0.056 Uiso calc R 1 . .
C C12 0.9333(2) 0.12360(18) 0.15011(18) 0.0395(4) Uani d . 1 . .
H H12A 1.0456 0.0863 0.0854 0.047 Uiso calc R 1 . .
H H12B 0.9376 0.1875 0.2080 0.047 Uiso calc R 1 . .
C C13 0.8246(2) 0.20204(18) 0.07324(16) 0.0374(4) Uani d . 1 . .
H H13A 0.8325 0.1414 0.0063 0.045 Uiso calc R 1 . .
H H13B 0.8637 0.2823 0.0238 0.045 Uiso calc R 1 . .
C C14 0.64620(19) 0.25206(16) 0.16682(15) 0.0323(3) Uani d . 1 . .
H H14A 0.5785 0.2953 0.1122 0.039 Uiso calc R 1 . .
H H14B 0.6358 0.3229 0.2252 0.039 Uiso calc R 1 . .
C C15 -0.20513(19) 0.48483(18) 0.78899(17) 0.0375(4) Uani d . 1 . .
H H15A -0.1830 0.5534 0.8284 0.056 Uiso calc R 1 . .
H H15B -0.2460 0.4176 0.8593 0.056 Uiso calc R 1 . .
H H15C -0.2874 0.5310 0.7494 0.056 Uiso calc R 1 . .
C C16 0.30487(18) 0.39021(16) 0.77290(15) 0.0285(3) Uani d . 1 . .
C C17 0.2397(2) 0.32608(18) 0.89640(16) 0.0358(4) Uani d . 1 . .
H H17 0.1250 0.3507 0.9451 0.043 Uiso calc R 1 . .
C C18 0.3418(2) 0.22589(19) 0.94899(17) 0.0407(4) Uani d . 1 . .
H H18 0.2994 0.1806 1.0337 0.049 Uiso calc R 1 . .
C C19 0.5066(2) 0.19413(17) 0.87463(18) 0.0364(4) Uani d . 1 . .
C C20 0.5741(2) 0.25692(19) 0.75227(18) 0.0392(4) Uani d . 1 . .
H H20 0.6888 0.2315 0.7036 0.047 Uiso calc R 1 . .
C C21 0.4712(2) 0.35849(18) 0.70112(16) 0.0351(4) Uani d . 1 . .
H H21 0.5145 0.4056 0.6178 0.042 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'
F F 0.0171 0.0103 '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'
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 C1 . . 108.26(7) ?
O2 S1 C16 . . 106.99(7) ?
C1 S1 C16 . . 98.14(7) ?
C8 O1 C7 . . 106.48(11) ?
C8 C1 C2 . . 107.33(14) ?
C8 C1 S1 . . 123.11(12) ?
C2 C1 S1 . . 129.47(11) ?
C7 C2 C3 . . 119.30(14) ?
C7 C2 C1 . . 104.57(13) ?
C3 C2 C1 . . 136.13(14) ?
C4 C3 C2 . . 118.81(14) ?
C4 C3 H3 . . 120.6 ?
C2 C3 H3 . . 120.6 ?
C3 C4 C5 . . 119.29(14) ?
C3 C4 C9 . . 120.33(14) ?
C5 C4 C9 . . 120.38(14) ?
C6 C5 C4 . . 122.88(15) ?
C6 C5 H5 . . 118.6 ?
C4 C5 H5 . . 118.6 ?
C7 C6 C5 . . 116.01(15) ?
C7 C6 H6 . . 122.0 ?
C5 C6 H6 . . 122.0 ?
C6 C7 O1 . . 125.54(14) ?
C6 C7 C2 . . 123.71(15) ?
O1 C7 C2 . . 110.75(13) ?
C1 C8 O1 . . 110.86(13) ?
C1 C8 C15 . . 133.48(16) ?
O1 C8 C15 . . 115.66(14) ?
C4 C9 C14 . . 111.53(13) ?
C4 C9 C10 . . 112.00(13) ?
C14 C9 C10 . . 110.18(14) ?
C4 C9 H9 . . 107.6 ?
C14 C9 H9 . . 107.6 ?
C10 C9 H9 . . 107.6 ?
C11 C10 C9 . . 111.25(14) ?
C11 C10 H10A . . 109.4 ?
C9 C10 H10A . . 109.4 ?
C11 C10 H10B . . 109.4 ?
C9 C10 H10B . . 109.4 ?
H10A C10 H10B . . 108.0 ?
C12 C11 C10 . . 111.13(14) ?
C12 C11 H11A . . 109.4 ?
C10 C11 H11A . . 109.4 ?
C12 C11 H11B . . 109.4 ?
C10 C11 H11B . . 109.4 ?
H11A C11 H11B . . 108.0 ?
C11 C12 C13 . . 111.33(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 . . 111.94(13) ?
C12 C13 H13A . . 109.2 ?
C14 C13 H13A . . 109.2 ?
C12 C13 H13B . . 109.2 ?
C14 C13 H13B . . 109.2 ?
H13A C13 H13B . . 107.9 ?
C13 C14 C9 . . 111.75(13) ?
C13 C14 H14A . . 109.3 ?
C9 C14 H14A . . 109.3 ?
C13 C14 H14B . . 109.3 ?
C9 C14 H14B . . 109.3 ?
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 . . 121.34(15) ?
C21 C16 S1 . . 119.74(12) ?
C17 C16 S1 . . 118.87(12) ?
C16 C17 C18 . . 119.85(15) ?
C16 C17 H17 . . 120.1 ?
C18 C17 H17 . . 120.1 ?
C19 C18 C17 . . 117.80(15) ?
C19 C18 H18 . . 121.1 ?
C17 C18 H18 . . 121.1 ?
F1 C19 C20 . . 118.26(15) ?
F1 C19 C18 . . 118.36(16) ?
C20 C19 C18 . . 123.37(16) ?
C19 C20 C21 . . 118.46(15) ?
C19 C20 H20 . . 120.8 ?
C21 C20 H20 . . 120.8 ?
C16 C21 C20 . . 119.14(15) ?
C16 C21 H21 . . 120.4 ?
C20 C21 H21 . . 120.4 ?
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 . 1.4852(12) ?
S1 C1 . 1.7524(16) ?
S1 C16 . 1.7956(16) ?
F1 C19 . 1.3588(19) ?
O1 C8 . 1.3685(19) ?
O1 C7 . 1.3824(18) ?
C1 C8 . 1.356(2) ?
C1 C2 . 1.450(2) ?
C2 C7 . 1.386(2) ?
C2 C3 . 1.396(2) ?
C3 C4 . 1.395(2) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.403(2) ?
C4 C9 . 1.513(2) ?
C5 C6 . 1.380(2) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.378(2) ?
C6 H6 . 0.9500 ?
C8 C15 . 1.481(2) ?
C9 C14 . 1.531(2) ?
C9 C10 . 1.533(2) ?
C9 H9 . 1.0000 ?
C10 C11 . 1.525(2) ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C11 C12 . 1.515(3) ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C12 C13 . 1.519(2) ?
C12 H12A . 0.9900 ?
C12 H12B . 0.9900 ?
C13 C14 . 1.528(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 . 1.380(2) ?
C16 C17 . 1.382(2) ?
C17 C18 . 1.385(2) ?
C17 H17 . 0.9500 ?
C18 C19 . 1.373(2) ?
C18 H18 . 0.9500 ?
C19 C20 . 1.371(2) ?
C20 C21 . 1.387(2) ?
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
C20 H20 O1 1_655 0.95 2.48 3.283(2) 142
C21 H21 O2 2_666 0.95 2.37 3.213(2) 148
C10 H10B Cg1 2_656 0.99 2.86 3.624(2) 135
C15 H15C Cg1 2_566 0.98 2.93 3.510(2) 119
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 . . . . -130.14(13) ?
C16 S1 C1 C8 . . . . 118.88(13) ?
O2 S1 C1 C2 . . . . 46.04(15) ?
C16 S1 C1 C2 . . . . -64.95(14) ?
C8 C1 C2 C7 . . . . -0.05(16) ?
S1 C1 C2 C7 . . . . -176.70(12) ?
C8 C1 C2 C3 . . . . 179.74(16) ?
S1 C1 C2 C3 . . . . 3.1(3) ?
C7 C2 C3 C4 . . . . -0.5(2) ?
C1 C2 C3 C4 . . . . 179.69(15) ?
C2 C3 C4 C5 . . . . 0.7(2) ?
C2 C3 C4 C9 . . . . -179.37(13) ?
C3 C4 C5 C6 . . . . -0.2(2) ?
C9 C4 C5 C6 . . . . 179.83(15) ?
C4 C5 C6 C7 . . . . -0.4(2) ?
C5 C6 C7 O1 . . . . -179.21(14) ?
C5 C6 C7 C2 . . . . 0.5(2) ?
C8 O1 C7 C6 . . . . -179.40(15) ?
C8 O1 C7 C2 . . . . 0.81(16) ?
C3 C2 C7 C6 . . . . -0.1(2) ?
C1 C2 C7 C6 . . . . 179.74(14) ?
C3 C2 C7 O1 . . . . 179.70(12) ?
C1 C2 C7 O1 . . . . -0.47(16) ?
C2 C1 C8 O1 . . . . 0.56(17) ?
S1 C1 C8 O1 . . . . 177.47(10) ?
C2 C1 C8 C15 . . . . -179.45(15) ?
S1 C1 C8 C15 . . . . -2.5(3) ?
C7 O1 C8 C1 . . . . -0.84(16) ?
C7 O1 C8 C15 . . . . 179.16(12) ?
C3 C4 C9 C14 . . . . -62.29(18) ?
C5 C4 C9 C14 . . . . 117.66(16) ?
C3 C4 C9 C10 . . . . 61.72(19) ?
C5 C4 C9 C10 . . . . -118.33(17) ?
C4 C9 C10 C11 . . . . 179.11(15) ?
C14 C9 C10 C11 . . . . -56.1(2) ?
C9 C10 C11 C12 . . . . 57.1(2) ?
C10 C11 C12 C13 . . . . -55.7(2) ?
C11 C12 C13 C14 . . . . 54.27(19) ?
C12 C13 C14 C9 . . . . -54.08(19) ?
C4 C9 C14 C13 . . . . 179.57(13) ?
C10 C9 C14 C13 . . . . 54.54(18) ?
O2 S1 C16 C21 . . . . -11.66(15) ?
C1 S1 C16 C21 . . . . 100.35(14) ?
O2 S1 C16 C17 . . . . 165.84(13) ?
C1 S1 C16 C17 . . . . -82.15(14) ?
C21 C16 C17 C18 . . . . -1.3(3) ?
S1 C16 C17 C18 . . . . -178.73(13) ?
C16 C17 C18 C19 . . . . 0.0(3) ?
C17 C18 C19 F1 . . . . -179.83(15) ?
C17 C18 C19 C20 . . . . 0.4(3) ?
F1 C19 C20 C21 . . . . -179.32(15) ?
C18 C19 C20 C21 . . . . 0.5(3) ?
C17 C16 C21 C20 . . . . 2.1(2) ?
S1 C16 C21 C20 . . . . 179.56(12) ?
C19 C20 C21 C16 . . . . -1.7(2) ?
