#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/02/2230298.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_2230298
loop_
_publ_author_name
'Choi, Hong Dae'
'Seo, Pil Ja'
'Son, Byeng Wha'
'Lee, Uk'
_publ_section_title
;
 3-(3-Fluorophenylsulfinyl)-2,5,7-trimethyl-1-benzofuran
;
_journal_coeditor_code           EZ2242
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1468
_journal_paper_doi               10.1107/S1600536811018654
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C17 H15 F O2 S'
_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-(3-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                110.701(3)
_cell_angle_beta                 100.176(3)
_cell_angle_gamma                103.621(2)
_cell_formula_units_Z            2
_cell_length_a                   6.2942(2)
_cell_length_b                   11.1162(4)
_cell_length_c                   11.8021(6)
_cell_measurement_reflns_used    5769
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      2.17
_cell_volume                     719.39(6)
_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      296(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  0.1222
_diffrn_reflns_av_sigmaI/netI    0.0684
_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            12696
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.92
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.237
_exptl_absorpt_correction_T_max  0.9510
_exptl_absorpt_correction_T_min  0.9346
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.515
_refine_diff_density_min         -0.442
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3301
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0466
_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)+(0.0679P)²+0.0860P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1269
_refine_ls_wR_factor_ref         0.1326
_reflns_number_gt                2760
_reflns_number_total             3301
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ez2242.cif
_cod_data_source_block           I
_cod_original_cell_volume        719.39(5)
_cod_database_code               2230298
_cod_database_fobs_code          2230298
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.61779(7) 0.50213(4) 0.83763(4) 0.02605(15) Uani d . 1 2 . .
O O1 0.2342(2) 0.38830(12) 0.49387(10) 0.0275(3) Uani d . 1 2 . .
O O2 0.8652(2) 0.52089(14) 0.85568(12) 0.0361(3) Uani d . 1 2 . .
F F1 0.7099(2) 0.14993(13) 1.00630(12) 0.0517(4) Uani d . 1 2 . .
C C1 0.4798(3) 0.42715(17) 0.67501(15) 0.0249(3) Uani d . 1 2 . .
C C2 0.5132(3) 0.31895(16) 0.57616(15) 0.0250(3) Uani d . 1 2 . .
C C3 0.6547(3) 0.23900(18) 0.56868(17) 0.0303(4) Uani d . 1 2 . .
H H3 0.7618 0.2516 0.6406 0.036 Uiso calc R 1 2 . .
C C4 0.6325(3) 0.14076(18) 0.45232(18) 0.0342(4) Uani d . 1 2 . .
C C5 0.4696(3) 0.12330(18) 0.34451(18) 0.0350(4) Uani d . 1 2 . .
H H5 0.4573 0.0561 0.2670 0.042 Uiso calc R 1 2 . .
C C6 0.3262(3) 0.20148(18) 0.34811(16) 0.0307(4) Uani d . 1 2 . .
C C7 0.3566(3) 0.29841(16) 0.46668(15) 0.0256(4) Uani d . 1 2 . .
C C8 0.3133(3) 0.46537(17) 0.62103(15) 0.0253(3) Uani d . 1 2 . .
C C9 0.7843(4) 0.0524(2) 0.4405(2) 0.0470(5) Uani d . 1 2 . .
H H9A 0.9238 0.0970 0.4290 0.070 Uiso calc R 1 2 . .
H H9B 0.7075 -0.0332 0.3691 0.070 Uiso calc R 1 2 . .
H H9C 0.8177 0.0373 0.5160 0.070 Uiso calc R 1 1 . .
C C10 0.1525(4) 0.1847(2) 0.23408(17) 0.0417(5) Uani d . 1 2 . .
H H10A 0.0034 0.1632 0.2459 0.063 Uiso calc R 1 2 . .
H H10B 0.1568 0.1125 0.1608 0.063 Uiso calc R 1 2 . .
H H10C 0.1863 0.2678 0.2226 0.063 Uiso calc R 1 2 . .
C C11 0.2019(3) 0.56740(18) 0.67277(17) 0.0324(4) Uani d . 1 2 . .
H H11A 0.0490 0.5220 0.6687 0.049 Uiso calc R 1 2 . .
H H11B 0.1982 0.6205 0.6241 0.049 Uiso calc R 1 2 . .
H H11C 0.2863 0.6259 0.7591 0.049 Uiso calc R 1 2 . .
C C12 0.5032(3) 0.35709(16) 0.86983(14) 0.0243(3) Uani d . 1 2 . .
C C13 0.6565(3) 0.30906(17) 0.92600(15) 0.0280(4) Uani d . 1 2 . .
H H13 0.8132 0.3478 0.9441 0.034 Uiso calc R 1 2 . .
C C14 0.5646(3) 0.20107(18) 0.95355(17) 0.0326(4) Uani d . 1 2 . .
C C15 0.3363(3) 0.14339(18) 0.93105(17) 0.0352(4) Uani d . 1 2 . .
H H15 0.2814 0.0706 0.9513 0.042 Uiso calc R 1 2 . .
C C16 0.1877(3) 0.19579(19) 0.87727(18) 0.0352(4) Uani d . 1 2 . .
H H16 0.0313 0.1583 0.8618 0.042 Uiso calc R 1 2 . .
C C17 0.2699(3) 0.30294(18) 0.84667(17) 0.0309(4) Uani d . 1 2 . .
H H17 0.1703 0.3384 0.8110 0.037 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'
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 . . 108.38(8) ?
O2 S1 C12 . . 105.93(7) ?
C1 S1 C12 . . 97.25(7) ?
C8 O1 C7 . . 106.64(12) ?
C8 C1 C2 . . 107.69(14) ?
C8 C1 S1 . . 123.27(13) ?
C2 C1 S1 . . 129.04(12) ?
C7 C2 C3 . . 119.25(15) ?
C7 C2 C1 . . 104.76(13) ?
C3 C2 C1 . . 135.99(15) ?
C4 C3 C2 . . 118.52(16) ?
C4 C3 H3 . . 120.7 ?
C2 C3 H3 . . 120.7 ?
C3 C4 C5 . . 119.93(16) ?
C3 C4 C9 . . 119.97(17) ?
C5 C4 C9 . . 120.09(18) ?
C6 C5 C4 . . 123.21(17) ?
C6 C5 H5 . . 118.4 ?
C4 C5 H5 . . 118.4 ?
C7 C6 C5 . . 114.34(16) ?
C7 C6 C10 . . 121.75(17) ?
C5 C6 C10 . . 123.91(17) ?
C6 C7 O1 . . 124.90(15) ?
C6 C7 C2 . . 124.74(15) ?
O1 C7 C2 . . 110.36(14) ?
C1 C8 O1 . . 110.54(14) ?
C1 C8 C11 . . 133.15(16) ?
O1 C8 C11 . . 116.28(13) ?
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 ?
C17 C12 C13 . . 121.95(16) ?
C17 C12 S1 . . 120.18(12) ?
C13 C12 S1 . . 117.72(13) ?
C14 C13 C12 . . 116.56(16) ?
C14 C13 H13 . . 121.7 ?
C12 C13 H13 . . 121.7 ?
F1 C14 C15 . . 118.44(17) ?
F1 C14 C13 . . 118.02(17) ?
C15 C14 C13 . . 123.54(16) ?
C14 C15 C16 . . 118.45(17) ?
C14 C15 H15 . . 120.8 ?
C16 C15 H15 . . 120.8 ?
C17 C16 C15 . . 120.52(17) ?
C17 C16 H16 . . 119.7 ?
C15 C16 H16 . . 119.7 ?
C16 C17 C12 . . 118.94(16) ?
C16 C17 H17 . . 120.5 ?
C12 C17 H17 . . 120.5 ?
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 . 1.4876(13) ?
S1 C1 . 1.7527(16) ?
S1 C12 . 1.8017(17) ?
O1 C8 . 1.3639(19) ?
O1 C7 . 1.3851(19) ?
F1 C14 . 1.357(2) ?
C1 C8 . 1.360(2) ?
C1 C2 . 1.437(2) ?
C2 C7 . 1.389(2) ?
C2 C3 . 1.391(2) ?
C3 C4 . 1.378(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.407(3) ?
C4 C9 . 1.513(2) ?
C5 C6 . 1.389(3) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.378(2) ?
C6 C10 . 1.499(2) ?
C8 C11 . 1.479(2) ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C12 C17 . 1.386(2) ?
C12 C13 . 1.386(2) ?
C13 C14 . 1.377(3) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.363(3) ?
C15 C16 . 1.388(3) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.377(3) ?
C16 H16 . 0.9300 ?
C17 H17 . 0.9300 ?
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 0.93 2.51 3.227(2) 134
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 . . . . -138.58(15) ?
C12 S1 C1 C8 . . . . 111.91(16) ?
O2 S1 C1 C2 . . . . 41.89(18) ?
C12 S1 C1 C2 . . . . -67.61(17) ?
C8 C1 C2 C7 . . . . -0.79(19) ?
S1 C1 C2 C7 . . . . 178.79(14) ?
C8 C1 C2 C3 . . . . 179.4(2) ?
S1 C1 C2 C3 . . . . -1.0(3) ?
C7 C2 C3 C4 . . . . -0.7(3) ?
C1 C2 C3 C4 . . . . 179.12(19) ?
C2 C3 C4 C5 . . . . 0.1(3) ?
C2 C3 C4 C9 . . . . 179.70(17) ?
C3 C4 C5 C6 . . . . 0.2(3) ?
C9 C4 C5 C6 . . . . -179.39(19) ?
C4 C5 C6 C7 . . . . 0.1(3) ?
C4 C5 C6 C10 . . . . 179.67(18) ?
C5 C6 C7 O1 . . . . 179.93(16) ?
C10 C6 C7 O1 . . . . 0.3(3) ?
C5 C6 C7 C2 . . . . -0.7(3) ?
C10 C6 C7 C2 . . . . 179.67(17) ?
C8 O1 C7 C6 . . . . 179.21(16) ?
C8 O1 C7 C2 . . . . -0.23(19) ?
C3 C2 C7 C6 . . . . 1.0(3) ?
C1 C2 C7 C6 . . . . -178.81(16) ?
C3 C2 C7 O1 . . . . -179.52(15) ?
C1 C2 C7 O1 . . . . 0.63(19) ?
C2 C1 C8 O1 . . . . 0.7(2) ?
S1 C1 C8 O1 . . . . -178.92(12) ?
C2 C1 C8 C11 . . . . 178.47(19) ?
S1 C1 C8 C11 . . . . -1.1(3) ?
C7 O1 C8 C1 . . . . -0.30(19) ?
C7 O1 C8 C11 . . . . -178.49(15) ?
O2 S1 C12 C17 . . . . -172.33(13) ?
C1 S1 C12 C17 . . . . -60.80(15) ?
O2 S1 C12 C13 . . . . 12.06(14) ?
C1 S1 C12 C13 . . . . 123.59(13) ?
C17 C12 C13 C14 . . . . 2.3(2) ?
S1 C12 C13 C14 . . . . 177.84(12) ?
C12 C13 C14 F1 . . . . 178.73(15) ?
C12 C13 C14 C15 . . . . -1.5(3) ?
F1 C14 C15 C16 . . . . 179.91(16) ?
C13 C14 C15 C16 . . . . 0.1(3) ?
C14 C15 C16 C17 . . . . 0.5(3) ?
C15 C16 C17 C12 . . . . 0.3(3) ?
C13 C12 C17 C16 . . . . -1.8(3) ?
S1 C12 C17 C16 . . . . -177.22(13) ?
