#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:42:48 +0200 (vie 13 de oct de 2017) $
#$Revision: 201978 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/99/2229988.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_2229988
loop_
_publ_author_name
'Seo, Pil Ja'
'Choi, Hong Dae'
'Lee, Uk'
_publ_section_title
;
 3-Cyclohexylsulfonyl-2,5-dimethyl-1-benzofuran
;
_journal_coeditor_code           GK2370
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1225
_journal_paper_doi               10.1107/S160053681101498X
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C16 H20 O3 S'
_chemical_formula_moiety         'C16 H20 O3 S'
_chemical_formula_sum            'C16 H20 O3 S'
_chemical_formula_weight         292.38
_chemical_name_systematic
;
3-Cyclohexylsulfonyl-2,5-dimethyl-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
_cell_angle_alpha                90.00
_cell_angle_beta                 99.295(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.6854(3)
_cell_length_b                   21.2391(13)
_cell_length_c                   12.3944(7)
_cell_measurement_reflns_used    4533
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.95
_cell_measurement_theta_min      2.54
_cell_volume                     1477.01(15)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0347
_diffrn_reflns_av_sigmaI/netI    0.0354
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13128
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.92
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.643
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.338
_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     183
_refine_ls_number_reflns         3228
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0400
_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)+(0.0473P)²+0.5178P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.1059
_reflns_number_gt                2477
_reflns_number_total             3228
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gk2370.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2229988
_cod_database_fobs_code          2229988
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.53749(8) 0.23293(2) 0.54070(4) 0.02970(14) Uani d . 1 2 . .
O O1 0.5649(2) 0.36998(6) 0.75483(10) 0.0354(3) Uani d . 1 2 . .
O O2 0.7773(2) 0.21003(7) 0.56894(12) 0.0420(4) Uani d . 1 2 . .
O O3 0.4559(2) 0.25126(6) 0.42912(10) 0.0388(3) Uani d . 1 2 . .
C C1 0.5009(3) 0.29734(8) 0.62295(14) 0.0296(4) Uani d . 1 2 . .
C C2 0.3075(3) 0.34199(8) 0.60232(14) 0.0284(4) Uani d . 1 2 . .
C C3 0.1036(3) 0.34955(8) 0.52479(14) 0.0309(4) Uani d . 1 2 . .
H H3 0.0678 0.3204 0.4663 0.037 Uiso calc R 1 2 . .
C C4 -0.0470(3) 0.39994(9) 0.53367(15) 0.0335(4) Uani d . 1 2 . .
C C5 0.0095(4) 0.44219(9) 0.62117(16) 0.0388(5) Uani d . 1 2 . .
H H5 -0.0956 0.4763 0.6272 0.047 Uiso calc R 1 2 . .
C C6 0.2113(4) 0.43607(9) 0.69861(16) 0.0392(5) Uani d . 1 2 . .
H H6 0.2484 0.4652 0.7571 0.047 Uiso calc R 1 2 . .
C C7 0.3561(3) 0.38557(8) 0.68658(14) 0.0315(4) Uani d . 1 2 . .
C C8 0.6487(3) 0.31577(9) 0.71474(14) 0.0332(4) Uani d . 1 2 . .
C C9 -0.2687(4) 0.40917(10) 0.45077(17) 0.0420(5) Uani d . 1 2 . .
H H9A -0.2263 0.4284 0.3846 0.063 Uiso calc R 1 2 . .
H H9B -0.3793 0.4368 0.4813 0.063 Uiso calc R 1 2 . .
H H9C -0.3449 0.3683 0.4324 0.063 Uiso calc R 1 2 . .
C C10 0.8718(3) 0.29097(11) 0.77813(16) 0.0409(5) Uani d . 1 2 . .
H H10A 0.9014 0.2485 0.7525 0.061 Uiso calc R 1 2 . .
H H10B 0.8573 0.2894 0.8558 0.061 Uiso calc R 1 2 . .
H H10C 1.0048 0.3186 0.7682 0.061 Uiso calc R 1 2 . .
C C11 0.3393(3) 0.17417(8) 0.57532(14) 0.0282(4) Uani d . 1 2 . .
H H11 0.1729 0.1907 0.5573 0.034 Uiso calc R 1 2 . .
C C12 0.3871(4) 0.15762(10) 0.69641(15) 0.0384(5) Uani d . 1 2 . .
H H12A 0.5537 0.1430 0.7169 0.046 Uiso calc R 1 2 . .
H H12B 0.3656 0.1955 0.7404 0.046 Uiso calc R 1 2 . .
C C13 0.2166(4) 0.10610(10) 0.72029(17) 0.0467(5) Uani d . 1 2 . .
H H13A 0.2528 0.0944 0.7985 0.056 Uiso calc R 1 2 . .
H H13B 0.0510 0.1222 0.7054 0.056 Uiso calc R 1 2 . .
C C14 0.2374(5) 0.04836(11) 0.65068(19) 0.0546(6) Uani d . 1 2 . .
H H14A 0.1200 0.0164 0.6655 0.066 Uiso calc R 1 2 . .
H H14B 0.3986 0.0300 0.6704 0.066 Uiso calc R 1 2 . .
C C15 0.1933(5) 0.06485(11) 0.52957(18) 0.0535(6) Uani d . 1 2 . .
H H15A 0.0263 0.0789 0.5082 0.064 Uiso calc R 1 2 . .
H H15B 0.2170 0.0269 0.4863 0.064 Uiso calc R 1 2 . .
C C16 0.3609(4) 0.11667(9) 0.50391(16) 0.0404(5) Uani d . 1 2 . .
H H16A 0.3208 0.1286 0.4259 0.049 Uiso calc R 1 2 . .
H H16B 0.5271 0.1011 0.5172 0.049 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'
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 . . 118.14(8) ?
O2 S1 C1 . . 108.80(9) ?
O3 S1 C1 . . 107.46(8) ?
O2 S1 C11 . . 108.47(8) ?
O3 S1 C11 . . 107.62(8) ?
C1 S1 C11 . . 105.67(8) ?
C8 O1 C7 . . 107.10(14) ?
C8 C1 C2 . . 108.03(16) ?
C8 C1 S1 . . 126.98(15) ?
C2 C1 S1 . . 124.96(13) ?
C7 C2 C3 . . 118.99(17) ?
C7 C2 C1 . . 104.56(16) ?
C3 C2 C1 . . 136.45(16) ?
C4 C3 C2 . . 119.42(17) ?
C4 C3 H3 . . 120.3 ?
C2 C3 H3 . . 120.3 ?
C3 C4 C5 . . 119.18(18) ?
C3 C4 C9 . . 120.43(17) ?
C5 C4 C9 . . 120.39(18) ?
C6 C5 C4 . . 122.59(18) ?
C6 C5 H5 . . 118.7 ?
C4 C5 H5 . . 118.7 ?
C7 C6 C5 . . 116.34(18) ?
C7 C6 H6 . . 121.8 ?
C5 C6 H6 . . 121.8 ?
C6 C7 O1 . . 126.21(16) ?
C6 C7 C2 . . 123.48(18) ?
O1 C7 C2 . . 110.31(16) ?
C1 C8 O1 . . 110.00(16) ?
C1 C8 C10 . . 134.80(19) ?
O1 C8 C10 . . 115.20(16) ?
C4 C9 H9A . . 109.5 ?
C4 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C4 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 . . 111.65(16) ?
C12 C11 S1 . . 112.35(12) ?
C16 C11 S1 . . 107.96(12) ?
C12 C11 H11 . . 108.2 ?
C16 C11 H11 . . 108.2 ?
S1 C11 H11 . . 108.2 ?
C13 C12 C11 . . 109.85(16) ?
C13 C12 H12A . . 109.7 ?
C11 C12 H12A . . 109.7 ?
C13 C12 H12B . . 109.7 ?
C11 C12 H12B . . 109.7 ?
H12A C12 H12B . . 108.2 ?
C14 C13 C12 . . 111.12(17) ?
C14 C13 H13A . . 109.4 ?
C12 C13 H13A . . 109.4 ?
C14 C13 H13B . . 109.4 ?
C12 C13 H13B . . 109.4 ?
H13A C13 H13B . . 108.0 ?
C13 C14 C15 . . 111.09(18) ?
C13 C14 H14A . . 109.4 ?
C15 C14 H14A . . 109.4 ?
C13 C14 H14B . . 109.4 ?
C15 C14 H14B . . 109.4 ?
H14A C14 H14B . . 108.0 ?
C14 C15 C16 . . 111.32(18) ?
C14 C15 H15A . . 109.4 ?
C16 C15 H15A . . 109.4 ?
C14 C15 H15B . . 109.4 ?
C16 C15 H15B . . 109.4 ?
H15A C15 H15B . . 108.0 ?
C15 C16 C11 . . 110.25(16) ?
C15 C16 H16A . . 109.6 ?
C11 C16 H16A . . 109.6 ?
C15 C16 H16B . . 109.6 ?
C11 C16 H16B . . 109.6 ?
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
S1 O2 . 1.4368(13) ?
S1 O3 . 1.4395(13) ?
S1 C1 . 1.7385(18) ?
S1 C11 . 1.7797(17) ?
O1 C8 . 1.369(2) ?
O1 C7 . 1.382(2) ?
C1 C8 . 1.358(3) ?
C1 C2 . 1.443(3) ?
C2 C7 . 1.390(2) ?
C2 C3 . 1.391(3) ?
C3 C4 . 1.386(3) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.404(3) ?
C4 C9 . 1.505(3) ?
C5 C6 . 1.378(3) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.375(3) ?
C6 H6 . 0.9500 ?
C8 C10 . 1.477(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 . 1.523(2) ?
C11 C16 . 1.525(3) ?
C11 H11 . 1.0000 ?
C12 C13 . 1.522(3) ?
C12 H12A . 0.9900 ?
C12 H12B . 0.9900 ?
C13 C14 . 1.515(3) ?
C13 H13A . 0.9900 ?
C13 H13B . 0.9900 ?
C14 C15 . 1.522(3) ?
C14 H14A . 0.9900 ?
C14 H14B . 0.9900 ?
C15 C16 . 1.522(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
C11 H11 O2 1_455 1.00 2.31 3.273(2) 161
C12 H12B O3 4_566 0.99 2.57 3.443(2) 146
C10 H10C Cg 1_655 0.99 2.75 3.556(2) 140
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 . . . . -13.71(19) ?
O3 S1 C1 C8 . . . . -142.70(16) ?
C11 S1 C1 C8 . . . . 102.59(17) ?
O2 S1 C1 C2 . . . . 164.31(14) ?
O3 S1 C1 C2 . . . . 35.31(17) ?
C11 S1 C1 C2 . . . . -79.39(16) ?
C8 C1 C2 C7 . . . . 0.08(18) ?
S1 C1 C2 C7 . . . . -178.25(13) ?
C8 C1 C2 C3 . . . . -179.33(19) ?
S1 C1 C2 C3 . . . . 2.3(3) ?
C7 C2 C3 C4 . . . . -0.5(2) ?
C1 C2 C3 C4 . . . . 178.88(18) ?
C2 C3 C4 C5 . . . . -0.2(3) ?
C2 C3 C4 C9 . . . . 179.96(16) ?
C3 C4 C5 C6 . . . . 0.7(3) ?
C9 C4 C5 C6 . . . . -179.43(18) ?
C4 C5 C6 C7 . . . . -0.6(3) ?
C5 C6 C7 O1 . . . . -179.30(16) ?
C5 C6 C7 C2 . . . . -0.2(3) ?
C8 O1 C7 C6 . . . . 178.52(17) ?
C8 O1 C7 C2 . . . . -0.71(18) ?
C3 C2 C7 C6 . . . . 0.7(3) ?
C1 C2 C7 C6 . . . . -178.87(17) ?
C3 C2 C7 O1 . . . . 179.92(14) ?
C1 C2 C7 O1 . . . . 0.39(18) ?
C2 C1 C8 O1 . . . . -0.52(19) ?
S1 C1 C8 O1 . . . . 177.76(12) ?
C2 C1 C8 C10 . . . . 179.59(19) ?
S1 C1 C8 C10 . . . . -2.1(3) ?
C7 O1 C8 C1 . . . . 0.76(19) ?
C7 O1 C8 C10 . . . . -179.33(15) ?
O2 S1 C11 C12 . . . . 59.13(15) ?
O3 S1 C11 C12 . . . . -171.99(13) ?
C1 S1 C11 C12 . . . . -57.40(15) ?
O2 S1 C11 C16 . . . . -64.43(15) ?
O3 S1 C11 C16 . . . . 64.46(14) ?
C1 S1 C11 C16 . . . . 179.05(13) ?
C16 C11 C12 C13 . . . . -57.1(2) ?
S1 C11 C12 C13 . . . . -178.58(14) ?
C11 C12 C13 C14 . . . . 56.9(2) ?
C12 C13 C14 C15 . . . . -56.7(2) ?
C13 C14 C15 C16 . . . . 55.8(3) ?
C14 C15 C16 C11 . . . . -55.3(3) ?
C12 C11 C16 C15 . . . . 56.4(2) ?
S1 C11 C16 C15 . . . . -179.62(15) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656634
