#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/17/2231717.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_2231717
loop_
_publ_author_name
'Seo, Pil Ja'
'Choi, Hong Dae'
'Son, Byeng Wha'
'Lee, Uk'
_publ_section_title
;
 3-(3-Fluorophenylsulfinyl)-2,4,5,6-tetramethyl-1-benzofuran
;
_journal_coeditor_code           VM2116
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2327
_journal_paper_doi               10.1107/S1600536811032077
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C18 H17 F O2 S'
_chemical_formula_moiety         'C18 H17 F O2 S'
_chemical_formula_sum            'C18 H17 F O2 S'
_chemical_formula_weight         316.38
_chemical_name_systematic
;
3-(3-Fluorophenylsulfinyl)-2,4,5,6-tetramethyl-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                93.089(9)
_cell_angle_beta                 104.812(9)
_cell_angle_gamma                103.368(9)
_cell_formula_units_Z            2
_cell_length_a                   8.1631(13)
_cell_length_b                   9.2105(14)
_cell_length_c                   10.9837(18)
_cell_measurement_reflns_used    4936
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.85
_cell_measurement_theta_min      2.81
_cell_volume                     771.1(2)
_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 0.983
_diffrn_measured_fraction_theta_max 0.983
_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  0.0327
_diffrn_reflns_av_sigmaI/netI    0.0363
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13358
_diffrn_reflns_theta_full        28.52
_diffrn_reflns_theta_max         28.52
_diffrn_reflns_theta_min         1.93
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.225
_exptl_absorpt_correction_T_max  0.9439
_exptl_absorpt_correction_T_min  0.9255
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.488
_refine_diff_density_min         -0.344
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3851
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0458
_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)+(0.0623P)²+0.2521P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1184
_refine_ls_wR_factor_ref         0.1313
_reflns_number_gt                2949
_reflns_number_total             3851
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            vm2116.cif
_cod_data_source_block           I
_cod_database_code               2231717
_cod_database_fobs_code          2231717
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
S S1 0.72575(6) 0.17448(5) 0.11804(5) 0.03550(15) Uani d . 1 2
O O1 0.79125(18) 0.60446(14) 0.10097(13) 0.0397(3) Uani d . 1 2
O O2 0.84594(17) 0.11260(15) 0.21415(15) 0.0468(4) Uani d . 1 2
F F1 0.2895(2) -0.15422(17) 0.30881(14) 0.0714(4) Uani d . 1 2
C C1 0.7609(2) 0.36974(19) 0.15447(18) 0.0326(4) Uani d . 1 2
C C2 0.7692(2) 0.46866(18) 0.26657(17) 0.0308(4) Uani d . 1 2
C C3 0.7630(2) 0.45329(19) 0.39109(17) 0.0328(4) Uani d . 1 2
C C4 0.7669(2) 0.5822(2) 0.46760(18) 0.0373(4) Uani d . 1 2
C C5 0.7842(2) 0.7238(2) 0.42159(19) 0.0383(4) Uani d . 1 2
C C6 0.7966(2) 0.7392(2) 0.29960(19) 0.0376(4) Uani d . 1 2
H H6 0.8108 0.8340 0.2681 0.045 Uiso calc R 1 2
C C7 0.7872(2) 0.6100(2) 0.22591(17) 0.0339(4) Uani d . 1 2
C C8 0.7739(3) 0.4571(2) 0.06027(19) 0.0378(4) Uani d . 1 2
C C9 0.7545(3) 0.3039(2) 0.44198(19) 0.0435(5) Uani d . 1 2
H H9A 0.6354 0.2603 0.4472 0.065 Uiso calc R 1 2
H H9B 0.8369 0.3183 0.5267 0.065 Uiso calc R 1 2
H H9C 0.7858 0.2359 0.3851 0.065 Uiso calc R 1 2
C C10 0.7545(3) 0.5700(3) 0.6016(2) 0.0526(5) Uani d . 1 2
H H10A 0.8724 0.5994 0.6605 0.079 Uiso calc R 1 2
H H10B 0.6979 0.4661 0.6090 0.079 Uiso calc R 1 2
H H10C 0.6852 0.6368 0.6222 0.079 Uiso calc R 1 2
C C11 0.7909(3) 0.8623(2) 0.5049(2) 0.0516(5) Uani d . 1 2
H H11A 0.8131 0.9508 0.4601 0.077 Uiso calc R 1 2
H H11B 0.8852 0.8748 0.5835 0.077 Uiso calc R 1 2
H H11C 0.6788 0.8511 0.5251 0.077 Uiso calc R 1 2
C C12 0.7644(3) 0.4258(3) -0.0756(2) 0.0547(6) Uani d . 1 2
H H12A 0.7929 0.3297 -0.0900 0.082 Uiso calc R 1 2
H H12B 0.8484 0.5064 -0.0988 0.082 Uiso calc R 1 2
H H12C 0.6458 0.4205 -0.1278 0.082 Uiso calc R 1 2
C C13 0.5135(2) 0.11544(18) 0.14512(17) 0.0316(4) Uani d . 1 2
C C14 0.3797(2) 0.1754(2) 0.0829(2) 0.0395(4) Uani d . 1 2
H H14 0.4004 0.2516 0.0297 0.047 Uiso calc R 1 2
C C15 0.2153(3) 0.1225(2) 0.0995(2) 0.0475(5) Uani d . 1 2
H H15 0.1225 0.1637 0.0578 0.057 Uiso calc R 1 2
C C16 0.1836(3) 0.0112(2) 0.1754(2) 0.0467(5) Uani d . 1 2
H H16 0.0703 -0.0248 0.1869 0.056 Uiso calc R 1 2
C C17 0.3193(3) -0.0457(2) 0.23361(19) 0.0423(5) Uani d . 1 2
C C18 0.4854(2) 0.0028(2) 0.22066(18) 0.0373(4) Uani d . 1 2
H H18 0.5773 -0.0396 0.2621 0.045 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'
F F 0.0171 0.0103 '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
O2 S1 C1 111.56(8)
O2 S1 C13 106.31(9)
C1 S1 C13 98.37(8)
C8 O1 C7 106.59(14)
C8 C1 C2 107.14(15)
C8 C1 S1 117.83(14)
C2 C1 S1 134.88(14)
C7 C2 C3 119.02(16)
C7 C2 C1 103.97(15)
C3 C2 C1 137.01(16)
C2 C3 C4 117.74(16)
C2 C3 C9 120.95(16)
C4 C3 C9 121.30(17)
C3 C4 C5 121.10(17)
C3 C4 C10 119.64(18)
C5 C4 C10 119.26(18)
C6 C5 C4 120.82(17)
C6 C5 C11 118.33(18)
C4 C5 C11 120.85(19)
C7 C6 C5 116.64(17)
C7 C6 H6 121.7
C5 C6 H6 121.7
C6 C7 O1 124.15(16)
C6 C7 C2 124.60(17)
O1 C7 C2 111.23(15)
C1 C8 O1 111.06(16)
C1 C8 C12 133.92(18)
O1 C8 C12 114.94(17)
C3 C9 H9A 109.5
C3 C9 H9B 109.5
H9A C9 H9B 109.5
C3 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C4 C10 H10A 109.5
C4 C10 H10B 109.5
H10A C10 H10B 109.5
C4 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C5 C11 H11A 109.5
C5 C11 H11B 109.5
H11A C11 H11B 109.5
C5 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
C18 C13 C14 121.52(17)
C18 C13 S1 118.72(14)
C14 C13 S1 119.58(14)
C13 C14 C15 118.69(19)
C13 C14 H14 120.7
C15 C14 H14 120.7
C16 C15 C14 121.15(19)
C16 C15 H15 119.4
C14 C15 H15 119.4
C17 C16 C15 118.01(19)
C17 C16 H16 121.0
C15 C16 H16 121.0
F1 C17 C16 118.40(19)
F1 C17 C18 118.29(19)
C16 C17 C18 123.3(2)
C17 C18 C13 117.31(18)
C17 C18 H18 121.3
C13 C18 H18 121.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O2 1.4818(14)
S1 C1 1.7613(17)
S1 C13 1.7975(18)
O1 C8 1.369(2)
O1 C7 1.380(2)
F1 C17 1.349(2)
C1 C8 1.355(3)
C1 C2 1.469(2)
C2 C7 1.387(2)
C2 C3 1.395(2)
C3 C4 1.406(3)
C3 C9 1.507(3)
C4 C5 1.414(3)
C4 C10 1.509(3)
C5 C6 1.382(3)
C5 C11 1.511(3)
C6 C7 1.378(2)
C6 H6 0.9500
C8 C12 1.484(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 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
C12 H12A 0.9800
C12 H12B 0.9800
C12 H12C 0.9800
C13 C18 1.378(3)
C13 C14 1.379(2)
C14 C15 1.380(3)
C14 H14 0.9500
C15 C16 1.376(3)
C15 H15 0.9500
C16 C17 1.362(3)
C16 H16 0.9500
C17 C18 1.373(3)
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 O1 2_665 0.95 2.51 3.232(2) 133.3
C16 H16 O2 1_455 0.95 2.52 3.224(2) 130.9
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
O2 S1 C1 C8 132.60(15)
C13 S1 C1 C8 -116.10(16)
O2 S1 C1 C2 -52.5(2)
C13 S1 C1 C2 58.80(19)
C8 C1 C2 C7 -0.08(19)
S1 C1 C2 C7 -175.35(15)
C8 C1 C2 C3 179.6(2)
S1 C1 C2 C3 4.3(3)
C7 C2 C3 C4 3.0(2)
C1 C2 C3 C4 -176.65(18)
C7 C2 C3 C9 -176.26(17)
C1 C2 C3 C9 4.1(3)
C2 C3 C4 C5 -2.6(3)
C9 C3 C4 C5 176.59(18)
C2 C3 C4 C10 178.03(17)
C9 C3 C4 C10 -2.7(3)
C3 C4 C5 C6 0.4(3)
C10 C4 C5 C6 179.75(18)
C3 C4 C5 C11 -179.15(17)
C10 C4 C5 C11 0.2(3)
C4 C5 C6 C7 1.4(3)
C11 C5 C6 C7 -179.02(17)
C5 C6 C7 O1 177.67(17)
C5 C6 C7 C2 -1.0(3)
C8 O1 C7 C6 -178.27(17)
C8 O1 C7 C2 0.6(2)
C3 C2 C7 C6 -1.2(3)
C1 C2 C7 C6 178.53(17)
C3 C2 C7 O1 179.95(15)
C1 C2 C7 O1 -0.31(19)
C2 C1 C8 O1 0.4(2)
S1 C1 C8 O1 176.66(12)
C2 C1 C8 C12 -176.0(2)
S1 C1 C8 C12 0.3(3)
C7 O1 C8 C1 -0.6(2)
C7 O1 C8 C12 176.51(17)
O2 S1 C13 C18 -14.81(17)
C1 S1 C13 C18 -130.29(15)
O2 S1 C13 C14 169.93(14)
C1 S1 C13 C14 54.46(16)
C18 C13 C14 C15 1.3(3)
S1 C13 C14 C15 176.42(15)
C13 C14 C15 C16 -0.6(3)
C14 C15 C16 C17 -0.2(3)
C15 C16 C17 F1 179.61(18)
C15 C16 C17 C18 0.3(3)
F1 C17 C18 C13 -178.93(17)
C16 C17 C18 C13 0.4(3)
C14 C13 C18 C17 -1.2(3)
S1 C13 C18 C17 -176.35(13)
