#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/49/2224934.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_2224934
loop_
_publ_author_name
'Choi, Hong Dae'
'Seo, Pil Ja'
'Son, Byeng Wha'
'Lee, Uk'
_publ_section_title
;
 3-(4-Fluorophenylsulfinyl)-2,5,7-trimethyl-1-benzofuran
;
_journal_coeditor_code           CV2691
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o472
_journal_paper_doi               10.1107/S160053681000293X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_moiety         'C17 H15 F O2 S'
_chemical_formula_sum            'C17 H15 F O2 S'
_chemical_formula_weight         302.35
_chemical_name_systematic
;
3-(4-Fluorophenylsulfinyl)-2,5,7-trimethyl-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                110.355(2)
_cell_angle_beta                 99.448(2)
_cell_angle_gamma                104.1300(10)
_cell_formula_units_Z            2
_cell_length_a                   6.2558(2)
_cell_length_b                   11.1848(3)
_cell_length_c                   11.9766(5)
_cell_measurement_reflns_used    9234
_cell_measurement_temperature    172(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      3.31
_cell_volume                     732.76(5)
_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      172(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Bruker HELIOS graded multilayer optics'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0208
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12781
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         1.89
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6807
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.371
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3350
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0361
_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)+(0.0539P)²+0.3002P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0990
_refine_ls_wR_factor_ref         0.1022
_reflns_number_gt                3071
_reflns_number_total             3350
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv2691.cif
_cod_data_source_block           I
_cod_original_cell_volume        732.75(4)
_cod_database_code               2224934
_cod_database_fobs_code          2224934
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 S 0.61072(6) 0.50406(3) 0.83633(3) 0.02837(11) Uani d . 1 . .
F F 0.28727(19) 0.04833(10) 0.97162(10) 0.0498(3) Uani d . 1 . .
O O1 0.23445(16) 0.38938(10) 0.49810(8) 0.0282(2) Uani d . 1 . .
O O2 0.86249(18) 0.53145(12) 0.85499(10) 0.0409(3) Uani d . 1 . .
C C1 0.4760(2) 0.42813(13) 0.67695(12) 0.0262(3) Uani d . 1 . .
C C2 0.5133(2) 0.32114(13) 0.58028(12) 0.0265(3) Uani d . 1 . .
C C3 0.6563(3) 0.24226(15) 0.57323(14) 0.0329(3) Uani d . 1 . .
H H3 0.7644 0.2546 0.6454 0.040 Uiso calc R 1 . .
C C4 0.6370(3) 0.14528(15) 0.45835(16) 0.0380(3) Uani d . 1 . .
C C5 0.4753(3) 0.12862(15) 0.35294(15) 0.0391(4) Uani d . 1 . .
H H5 0.4639 0.0608 0.2755 0.047 Uiso calc R 1 . .
C C6 0.3315(3) 0.20587(14) 0.35596(13) 0.0337(3) Uani d . 1 . .
C C7 0.3589(2) 0.30150(13) 0.47270(12) 0.0273(3) Uani d . 1 . .
C C8 0.3107(2) 0.46565(13) 0.62320(11) 0.0261(3) Uani d . 1 . .
C C9 0.7900(3) 0.05875(18) 0.4476(2) 0.0522(5) Uani d . 1 . .
H H9A 0.9355 0.1056 0.4379 0.078 Uiso calc R 1 . .
H H9B 0.7145 -0.0271 0.3754 0.078 Uiso calc R 1 . .
H H9C 0.8196 0.0416 0.5226 0.078 Uiso calc R 1 . .
C C10 0.1578(3) 0.19014(17) 0.24463(14) 0.0464(4) Uani d . 1 . .
H H10A 0.0033 0.1588 0.2532 0.070 Uiso calc R 1 . .
H H10B 0.1734 0.1242 0.1698 0.070 Uiso calc R 1 . .
H H10C 0.1834 0.2772 0.2382 0.070 Uiso calc R 1 . .
C C11 0.1968(3) 0.56646(15) 0.67177(13) 0.0337(3) Uani d . 1 . .
H H11A 0.0400 0.5202 0.6690 0.051 Uiso calc R 1 . .
H H11B 0.1925 0.6186 0.6210 0.051 Uiso calc R 1 . .
H H11C 0.2823 0.6274 0.7575 0.051 Uiso calc R 1 . .
C C12 0.5089(2) 0.35932(13) 0.87080(11) 0.0264(3) Uani d . 1 . .
C C13 0.6686(2) 0.31841(15) 0.92889(12) 0.0310(3) Uani d . 1 . .
H H13 0.8279 0.3625 0.9454 0.037 Uiso calc R 1 . .
C C14 0.5933(3) 0.21171(15) 0.96292(13) 0.0350(3) Uani d . 1 . .
H H14 0.6994 0.1810 1.0023 0.042 Uiso calc R 1 . .
C C15 0.3616(3) 0.15211(14) 0.93807(13) 0.0348(3) Uani d . 1 . .
C C16 0.1997(3) 0.19321(15) 0.88255(14) 0.0361(3) Uani d . 1 . .
H H16 0.0407 0.1499 0.8678 0.043 Uiso calc R 1 . .
C C17 0.2753(2) 0.29939(15) 0.84890(13) 0.0326(3) Uani d . 1 . .
H H17 0.1683 0.3309 0.8112 0.039 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 S C1 . . 108.53(6) ?
O2 S C12 . . 105.94(6) ?
C1 S C12 . . 97.96(6) ?
C8 O1 C7 . . 106.44(10) ?
C8 C1 C2 . . 107.66(11) ?
C8 C1 S . . 122.90(10) ?
C2 C1 S . . 129.43(10) ?
C7 C2 C3 . . 119.26(13) ?
C7 C2 C1 . . 104.44(11) ?
C3 C2 C1 . . 136.30(13) ?
C4 C3 C2 . . 118.46(14) ?
C4 C3 H3 . . 120.8 ?
C2 C3 H3 . . 120.8 ?
C3 C4 C5 . . 119.76(14) ?
C3 C4 C9 . . 119.71(16) ?
C5 C4 C9 . . 120.53(15) ?
C6 C5 C4 . . 123.51(14) ?
C6 C5 H5 . . 118.2 ?
C4 C5 H5 . . 118.2 ?
C7 C6 C5 . . 114.30(14) ?
C7 C6 C10 . . 121.21(15) ?
C5 C6 C10 . . 124.49(14) ?
O1 C7 C6 . . 124.51(13) ?
O1 C7 C2 . . 110.78(11) ?
C6 C7 C2 . . 124.70(13) ?
C1 C8 O1 . . 110.67(11) ?
C1 C8 C11 . . 133.59(12) ?
O1 C8 C11 . . 115.72(11) ?
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 ?
C6 C10 H10A . . 109.5 ?
C6 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C6 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C8 C11 H11A . . 109.5 ?
C8 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C8 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C13 C12 C17 . . 121.61(13) ?
C13 C12 S . . 118.26(11) ?
C17 C12 S . . 119.88(11) ?
C12 C13 C14 . . 119.19(13) ?
C12 C13 H13 . . 120.4 ?
C14 C13 H13 . . 120.4 ?
C15 C14 C13 . . 118.22(14) ?
C15 C14 H14 . . 120.9 ?
C13 C14 H14 . . 120.9 ?
F C15 C14 . . 118.43(14) ?
F C15 C16 . . 118.07(14) ?
C14 C15 C16 . . 123.49(14) ?
C15 C16 C17 . . 118.13(14) ?
C15 C16 H16 . . 120.9 ?
C17 C16 H16 . . 120.9 ?
C16 C17 C12 . . 119.34(14) ?
C16 C17 H17 . . 120.3 ?
C12 C17 H17 . . 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 O2 . 1.4919(11) ?
S C1 . 1.7521(13) ?
S C12 . 1.8013(14) ?
F C15 . 1.3591(17) ?
O1 C8 . 1.3702(15) ?
O1 C7 . 1.3814(16) ?
C1 C8 . 1.3567(19) ?
C1 C2 . 1.4450(18) ?
C2 C7 . 1.3899(19) ?
C2 C3 . 1.3942(19) ?
C3 C4 . 1.388(2) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.406(2) ?
C4 C9 . 1.509(2) ?
C5 C6 . 1.387(2) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.3856(19) ?
C6 C10 . 1.503(2) ?
C8 C11 . 1.4799(19) ?
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 C13 . 1.3811(19) ?
C12 C17 . 1.3885(19) ?
C13 C14 . 1.393(2) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.372(2) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.378(2) ?
C16 C17 . 1.385(2) ?
C16 H16 . 0.9500 ?
C17 H17 . 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
C13 H13 O2 2_767 0.95 2.50 3.194(2) 129.8
C11 H11B Cg 2_666 0.98 2.87 3.663(2) 138.6
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 S C1 C8 . . . . -134.93(12) ?
C12 S C1 C8 . . . . 115.24(12) ?
O2 S C1 C2 . . . . 44.44(14) ?
C12 S C1 C2 . . . . -65.40(13) ?
C8 C1 C2 C7 . . . . -0.82(15) ?
S C1 C2 C7 . . . . 179.74(11) ?
C8 C1 C2 C3 . . . . 179.13(15) ?
S C1 C2 C3 . . . . -0.3(2) ?
C7 C2 C3 C4 . . . . -0.7(2) ?
C1 C2 C3 C4 . . . . 179.31(15) ?
C2 C3 C4 C5 . . . . -0.2(2) ?
C2 C3 C4 C9 . . . . 179.74(13) ?
C3 C4 C5 C6 . . . . 0.8(2) ?
C9 C4 C5 C6 . . . . -179.12(14) ?
C4 C5 C6 C7 . . . . -0.4(2) ?
C4 C5 C6 C10 . . . . 179.89(15) ?
C8 O1 C7 C6 . . . . 179.37(13) ?
C8 O1 C7 C2 . . . . 0.00(14) ?
C5 C6 C7 O1 . . . . -179.85(12) ?
C10 C6 C7 O1 . . . . -0.2(2) ?
C5 C6 C7 C2 . . . . -0.6(2) ?
C10 C6 C7 C2 . . . . 179.13(14) ?
C3 C2 C7 O1 . . . . -179.46(12) ?
C1 C2 C7 O1 . . . . 0.50(14) ?
C3 C2 C7 C6 . . . . 1.2(2) ?
C1 C2 C7 C6 . . . . -178.86(13) ?
C2 C1 C8 O1 . . . . 0.87(15) ?
S C1 C8 O1 . . . . -179.65(9) ?
C2 C1 C8 C11 . . . . 179.02(14) ?
S C1 C8 C11 . . . . -1.5(2) ?
C7 O1 C8 C1 . . . . -0.55(15) ?
C7 O1 C8 C11 . . . . -179.07(11) ?
O2 S C12 C13 . . . . 12.66(12) ?
C1 S C12 C13 . . . . 124.61(11) ?
O2 S C12 C17 . . . . -172.98(11) ?
C1 S C12 C17 . . . . -61.03(12) ?
C17 C12 C13 C14 . . . . 2.0(2) ?
S C12 C13 C14 . . . . 176.26(10) ?
C12 C13 C14 C15 . . . . -0.6(2) ?
C13 C14 C15 F . . . . -179.71(12) ?
C13 C14 C15 C16 . . . . -0.8(2) ?
F C15 C16 C17 . . . . 179.68(13) ?
C14 C15 C16 C17 . . . . 0.7(2) ?
C15 C16 C17 C12 . . . . 0.7(2) ?
C13 C12 C17 C16 . . . . -2.0(2) ?
S C12 C17 C16 . . . . -176.20(11) ?
