#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/60/2226026.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_2226026
loop_
_publ_author_name
'Choi, Hong Dae'
'Seo, Pil Ja'
'Son, Byeng Wha'
'Lee, Uk'
_publ_section_title
;
 3-(4-Fluorophenylsulfonyl)-5-isopropyl-2-methyl-1-benzofuran
;
_journal_coeditor_code           XU2750
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1067
_journal_paper_doi               10.1107/S1600536810012869
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C18 H17 F O3 S'
_chemical_formula_moiety         'C18 H17 F O3 S'
_chemical_formula_sum            'C18 H17 F O3 S'
_chemical_formula_weight         332.38
_chemical_name_systematic
;
3-(4-Fluorophenylsulfonyl)-5-isopropyl-2-methyl-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                 100.252(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.9434(6)
_cell_length_b                   11.3395(6)
_cell_length_c                   13.0988(7)
_cell_measurement_reflns_used    6367
_cell_measurement_temperature    175(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.39
_cell_volume                     1599.51(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      175(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 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  0.0296
_diffrn_reflns_av_sigmaI/netI    0.0273
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14304
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.39
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.225
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6694
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.412
_exptl_crystal_size_mid          0.288
_exptl_crystal_size_min          0.172
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.366
_refine_ls_extinction_coef       0.0117(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3655
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0372
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0594P)²+0.4509P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1014
_refine_ls_wR_factor_ref         0.1075
_reflns_number_gt                3109
_reflns_number_total             3655
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2750.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2226026
_cod_database_fobs_code          2226026
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_disorder_assembly
_atom_site_disorder_group
S S 0.54221(3) 0.13196(3) 0.21925(3) 0.02922(13) Uani d . 1 . .
F F 0.75485(9) -0.21439(9) -0.02852(8) 0.0475(3) Uani d . 1 . .
O O1 0.44396(10) 0.07695(11) 0.26153(9) 0.0415(3) Uani d . 1 . .
O O2 0.51752(10) 0.23800(9) 0.15885(8) 0.0367(3) Uani d . 1 . .
O O3 0.79447(10) 0.15165(9) 0.47328(8) 0.0300(2) Uani d . 1 . .
C C1 0.66335(13) 0.16383(12) 0.32124(11) 0.0268(3) Uani d . 1 . .
C C2 0.75540(12) 0.25570(12) 0.32202(10) 0.0244(3) Uani d . 1 . .
C C3 0.78117(13) 0.34256(12) 0.25361(11) 0.0270(3) Uani d . 1 . .
H H3 0.7288 0.3527 0.1881 0.032 Uiso calc R 1 . .
C C4 0.88480(13) 0.41423(13) 0.28261(11) 0.0285(3) Uani d . 1 . .
C C5 0.96004(13) 0.39900(13) 0.38020(11) 0.0302(3) Uani d . 1 . .
H H5 1.0300 0.4491 0.3993 0.036 Uiso calc R 1 . .
C C6 0.93628(13) 0.31367(13) 0.44994(11) 0.0297(3) Uani d . 1 . .
H H6 0.9877 0.3038 0.5159 0.036 Uiso calc R 1 . .
C C7 0.83340(13) 0.24398(12) 0.41752(10) 0.0257(3) Uani d . 1 . .
C C8 0.69246(14) 0.10323(13) 0.41204(11) 0.0303(3) Uani d . 1 . .
C C9 0.91774(15) 0.50549(14) 0.20723(12) 0.0356(4) Uani d . 1 . .
H H9 0.8483 0.5073 0.1462 0.043 Uiso calc R 1 . .
C C10 1.0351(2) 0.47032(18) 0.16761(16) 0.0548(5) Uani d . 1 . .
H H10A 1.1061 0.4728 0.2249 0.082 Uiso calc R 1 . .
H H10B 1.0492 0.5253 0.1132 0.082 Uiso calc R 1 . .
H H10C 1.0256 0.3902 0.1392 0.082 Uiso calc R 1 . .
C C11 0.9299(2) 0.62926(15) 0.25374(16) 0.0531(5) Uani d . 1 . .
H H11A 0.8558 0.6477 0.2832 0.080 Uiso calc R 1 . .
H H11B 0.9381 0.6866 0.1994 0.080 Uiso calc R 1 . .
H H11C 1.0036 0.6329 0.3085 0.080 Uiso calc R 1 . .
C C12 0.64435(18) -0.00464(15) 0.45463(14) 0.0452(4) Uani d . 1 . .
H H12A 0.5675 -0.0294 0.4094 0.068 Uiso calc R 1 . .
H H12B 0.6275 0.0117 0.5243 0.068 Uiso calc R 1 . .
H H12C 0.7062 -0.0677 0.4584 0.068 Uiso calc R 1 . .
C C13 0.60386(13) 0.02725(12) 0.14291(11) 0.0274(3) Uani d . 1 . .
C C14 0.60321(15) -0.09153(13) 0.16991(12) 0.0342(3) Uani d . 1 . .
H H14 0.5684 -0.1159 0.2279 0.041 Uiso calc R 1 . .
C C15 0.65382(15) -0.17364(14) 0.11133(13) 0.0375(4) Uani d . 1 . .
H H15 0.6546 -0.2551 0.1283 0.045 Uiso calc R 1 . .
C C16 0.70315(14) -0.13427(13) 0.02763(13) 0.0332(3) Uani d . 1 . .
C C17 0.70304(14) -0.01834(14) -0.00155(12) 0.0344(3) Uani d . 1 . .
H H17 0.7364 0.0049 -0.0606 0.041 Uiso calc R 1 . .
C C18 0.65300(14) 0.06423(13) 0.05734(12) 0.0309(3) Uani d . 1 . .
H H18 0.6523 0.1454 0.0394 0.037 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
O1 S O2 . . 119.66(7) ?
O1 S C1 . . 108.28(7) ?
O2 S C1 . . 106.91(7) ?
O1 S C13 . . 108.33(7) ?
O2 S C13 . . 107.74(7) ?
C1 S C13 . . 104.99(7) ?
C8 O3 C7 . . 106.82(11) ?
C8 C1 C2 . . 107.62(13) ?
C8 C1 S . . 126.33(11) ?
C2 C1 S . . 125.97(11) ?
C7 C2 C3 . . 118.96(12) ?
C7 C2 C1 . . 104.63(12) ?
C3 C2 C1 . . 136.39(13) ?
C4 C3 C2 . . 119.04(13) ?
C4 C3 H3 . . 120.5 ?
C2 C3 H3 . . 120.5 ?
C3 C4 C5 . . 119.64(13) ?
C3 C4 C9 . . 119.80(13) ?
C5 C4 C9 . . 120.53(13) ?
C6 C5 C4 . . 122.53(13) ?
C6 C5 H5 . . 118.7 ?
C4 C5 H5 . . 118.7 ?
C7 C6 C5 . . 115.82(13) ?
C7 C6 H6 . . 122.1 ?
C5 C6 H6 . . 122.1 ?
C6 C7 O3 . . 125.53(13) ?
C6 C7 C2 . . 124.01(13) ?
O3 C7 C2 . . 110.45(12) ?
C1 C8 O3 . . 110.44(13) ?
C1 C8 C12 . . 134.67(15) ?
O3 C8 C12 . . 114.75(13) ?
C4 C9 C10 . . 110.85(14) ?
C4 C9 C11 . . 112.42(13) ?
C10 C9 C11 . . 110.99(15) ?
C4 C9 H9 . . 107.4 ?
C10 C9 H9 . . 107.4 ?
C11 C9 H9 . . 107.4 ?
C9 C10 H10A . . 109.5 ?
C9 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C9 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C9 C11 H11A . . 109.5 ?
C9 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C9 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C8 C12 H12A . . 109.5 ?
C8 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C8 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C14 C13 C18 . . 121.08(14) ?
C14 C13 S . . 119.19(11) ?
C18 C13 S . . 119.73(11) ?
C15 C14 C13 . . 119.29(14) ?
C15 C14 H14 . . 120.4 ?
C13 C14 H14 . . 120.4 ?
C16 C15 C14 . . 118.36(14) ?
C16 C15 H15 . . 120.8 ?
C14 C15 H15 . . 120.8 ?
F C16 C17 . . 118.17(14) ?
F C16 C15 . . 118.35(14) ?
C17 C16 C15 . . 123.48(14) ?
C16 C17 C18 . . 118.29(14) ?
C16 C17 H17 . . 120.9 ?
C18 C17 H17 . . 120.9 ?
C17 C18 C13 . . 119.49(14) ?
C17 C18 H18 . . 120.3 ?
C13 C18 H18 . . 120.3 ?
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
S O1 . 1.4370(10) ?
S O2 . 1.4380(10) ?
S C1 . 1.744(2) ?
S C13 . 1.7620(10) ?
F C16 . 1.355(2) ?
O3 C8 . 1.368(2) ?
O3 C7 . 1.386(2) ?
C1 C8 . 1.361(2) ?
C1 C2 . 1.448(2) ?
C2 C7 . 1.390(2) ?
C2 C3 . 1.394(2) ?
C3 C4 . 1.392(2) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.403(2) ?
C4 C9 . 1.517(2) ?
C5 C6 . 1.387(2) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.379(2) ?
C6 H6 . 0.9500 ?
C8 C12 . 1.480(2) ?
C9 C10 . 1.521(2) ?
C9 C11 . 1.526(2) ?
C9 H9 . 1.0000 ?
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 H12A . 0.9800 ?
C12 H12B . 0.9800 ?
C12 H12C . 0.9800 ?
C13 C14 . 1.393(2) ?
C13 C18 . 1.391(2) ?
C14 C15 . 1.383(2) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.380(2) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.369(2) ?
C17 C18 . 1.386(2) ?
C17 H17 . 0.9500 ?
C18 H18 . 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
C14 H14 O2 2_645 0.95 2.51 3.401(2) 155.4
C10 H10B Cg1 2_755 0.98 2.86 3.561(2) 120.0
C11 H11B Cg2 2_755 0.98 2.91 3.670(2) 134.7
C17 H17 Cg2 2_745 0.95 2.89 3.528(2) 146.8
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744849
