#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2223865.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_2223865
loop_
_publ_author_name
'Choi, Hong Dae'
'Seo, Pil Ja'
'Son, Byeng Wha'
'Lee, Uk'
_publ_section_title
;
 5-Fluoro-2-(4-fluorophenyl)-3-methylsulfinyl-1-benzofuran
;
_journal_coeditor_code           IS2465
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2608
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C15 H10 F2 O2 S'
_chemical_formula_moiety         'C15 H10 F2 O2 S'
_chemical_formula_sum            'C15 H10 F2 O2 S'
_chemical_formula_weight         292.29
_chemical_name_systematic
;
5-Fluoro-2-(4-fluorophenyl)-3-methylsulfinyl-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                97.033(2)
_cell_angle_beta                 91.516(2)
_cell_angle_gamma                113.533(2)
_cell_formula_units_Z            2
_cell_length_a                   7.9275(3)
_cell_length_b                   8.2069(3)
_cell_length_c                   10.6822(4)
_cell_measurement_reflns_used    8044
_cell_measurement_temperature    172(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      2.74
_cell_volume                     630.22(4)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD'
_diffrn_measurement_method       '\f and \w'
_diffrn_radiation_monochromator  HELIOS
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_sigmaI/netI    0.0177
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10883
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    0.279
_exptl_absorpt_correction_T_max  0.9678
_exptl_absorpt_correction_T_min  0.8878
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(<i>APEX2</i>; Bruker, 2009)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.296
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2900
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0301
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0414P)^2^+0.2389P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0810
_refine_ls_wR_factor_ref         0.0838
_reflns_number_gt                2661
_reflns_number_total             2900
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    is2465.cif
_[local]_cod_data_source_block   I
_cod_database_code               2223865
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
S S 0.17610(4) 0.19867(4) 0.58632(3) 0.02317(10) Uani d . 1
F F1 0.56623(14) 0.77195(13) 0.99398(8) 0.0443(2) Uani d . 1
F F2 -0.04941(15) 0.22620(14) -0.02234(8) 0.0495(3) Uani d . 1
O O1 0.33749(13) 0.69196(11) 0.49937(8) 0.0246(2) Uani d . 1
O O2 0.31172(14) 0.17318(13) 0.67238(10) 0.0348(2) Uani d . 1
C C1 0.25777(17) 0.43064(16) 0.57768(11) 0.0217(2) Uani d . 1
C C2 0.35892(17) 0.57414(16) 0.67846(12) 0.0230(2) Uani d . 1
C C3 0.41294(19) 0.58468(18) 0.80585(12) 0.0272(3) Uani d . 1
H H3 0.3843 0.4807 0.8459 0.033 Uiso calc R 1
C C4 0.5103(2) 0.7554(2) 0.86950(13) 0.0312(3) Uani d . 1
C C5 0.5563(2) 0.91200(19) 0.81591(14) 0.0327(3) Uani d . 1
H H5 0.6239 1.0255 0.8656 0.039 Uiso calc R 1
C C6 0.50286(19) 0.90178(18) 0.68960(14) 0.0291(3) Uani d . 1
H H6 0.5316 1.0062 0.6500 0.035 Uiso calc R 1
C C7 0.40540(17) 0.73123(17) 0.62445(12) 0.0239(3) Uani d . 1
C C8 0.24884(17) 0.50769(16) 0.47293(12) 0.0222(2) Uani d . 1
C C9 0.16701(17) 0.43530(17) 0.34357(11) 0.0223(2) Uani d . 1
C C10 0.01310(18) 0.27185(18) 0.31677(12) 0.0258(3) Uani d . 1
H H10 -0.0425 0.2097 0.3843 0.031 Uiso calc R 1
C C11 -0.05978(19) 0.19894(19) 0.19358(13) 0.0299(3) Uani d . 1
H H11 -0.1622 0.0861 0.1751 0.036 Uiso calc R 1
C C12 0.0214(2) 0.2958(2) 0.09877(12) 0.0316(3) Uani d . 1
C C13 0.1700(2) 0.45994(19) 0.12075(13) 0.0311(3) Uani d . 1
H H13 0.2203 0.5238 0.0528 0.037 Uiso calc R 1
C C14 0.24436(19) 0.52965(17) 0.24403(12) 0.0259(3) Uani d . 1
H H14 0.3481 0.6417 0.2612 0.031 Uiso calc R 1
C C15 -0.01622(19) 0.18188(19) 0.67642(13) 0.0295(3) Uani d . 1
H H15A -0.0741 0.0608 0.6994 0.044 Uiso calc R 1
H H15B -0.1065 0.2056 0.6257 0.044 Uiso calc R 1
H H15C 0.0268 0.2701 0.7535 0.044 Uiso calc R 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S 0.02566(18) 0.01834(16) 0.02506(16) 0.00839(13) 0.00392(12) 0.00302(11)
F1 0.0527(6) 0.0458(5) 0.0260(4) 0.0155(5) -0.0092(4) -0.0068(4)
F2 0.0558(6) 0.0565(6) 0.0222(4) 0.0102(5) -0.0081(4) 0.0014(4)
O1 0.0261(5) 0.0193(4) 0.0262(4) 0.0072(4) 0.0005(3) 0.0036(3)
O2 0.0290(5) 0.0301(5) 0.0493(6) 0.0136(4) 0.0013(4) 0.0148(4)
C1 0.0229(6) 0.0194(6) 0.0219(6) 0.0081(5) 0.0023(5) 0.0017(4)
C2 0.0217(6) 0.0214(6) 0.0257(6) 0.0093(5) 0.0023(5) 0.0011(5)
C3 0.0291(7) 0.0281(6) 0.0249(6) 0.0129(6) 0.0008(5) 0.0010(5)
C4 0.0305(7) 0.0354(7) 0.0252(6) 0.0135(6) -0.0028(5) -0.0041(5)
C5 0.0275(7) 0.0262(7) 0.0376(7) 0.0078(6) -0.0024(6) -0.0076(5)
C6 0.0251(7) 0.0210(6) 0.0381(7) 0.0071(5) 0.0009(5) 0.0007(5)
C7 0.0220(6) 0.0234(6) 0.0263(6) 0.0097(5) 0.0014(5) 0.0018(5)
C8 0.0205(6) 0.0194(6) 0.0257(6) 0.0073(5) 0.0028(5) 0.0023(4)
C9 0.0225(6) 0.0235(6) 0.0228(6) 0.0113(5) 0.0021(5) 0.0033(5)
C10 0.0241(6) 0.0280(6) 0.0241(6) 0.0085(5) 0.0028(5) 0.0065(5)
C11 0.0252(7) 0.0304(7) 0.0297(7) 0.0074(6) -0.0026(5) 0.0024(5)
C12 0.0333(7) 0.0398(8) 0.0208(6) 0.0152(6) -0.0032(5) 0.0016(5)
C13 0.0349(7) 0.0351(7) 0.0251(6) 0.0145(6) 0.0061(5) 0.0095(5)
C14 0.0266(6) 0.0241(6) 0.0273(6) 0.0100(5) 0.0041(5) 0.0058(5)
C15 0.0284(7) 0.0295(7) 0.0318(7) 0.0118(6) 0.0088(5) 0.0077(5)
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
O2 S C1 107.26(6)
O2 S C15 106.17(6)
C1 S C15 97.08(6)
C7 O1 C8 106.55(9)
C8 C1 C2 107.21(11)
C8 C1 S 126.69(10)
C2 C1 S 125.96(9)
C7 C2 C3 119.65(12)
C7 C2 C1 105.04(11)
C3 C2 C1 135.31(12)
C4 C3 C2 115.71(13)
C4 C3 H3 122.1
C2 C3 H3 122.1
F1 C4 C3 117.70(13)
F1 C4 C5 117.60(12)
C3 C4 C5 124.70(13)
C6 C5 C4 119.67(13)
C6 C5 H5 120.2
C4 C5 H5 120.2
C7 C6 C5 116.25(13)
C7 C6 H6 121.9
C5 C6 H6 121.9
O1 C7 C6 125.41(12)
O1 C7 C2 110.56(11)
C6 C7 C2 124.02(12)
C1 C8 O1 110.64(11)
C1 C8 C9 133.40(12)
O1 C8 C9 115.96(10)
C10 C9 C14 119.18(12)
C10 C9 C8 121.02(11)
C14 C9 C8 119.79(12)
C11 C10 C9 121.14(12)
C11 C10 H10 119.4
C9 C10 H10 119.4
C12 C11 C10 117.62(13)
C12 C11 H11 121.2
C10 C11 H11 121.2
F2 C12 C11 118.17(13)
F2 C12 C13 118.46(12)
C11 C12 C13 123.37(13)
C12 C13 C14 118.51(12)
C12 C13 H13 120.7
C14 C13 H13 120.7
C13 C14 C9 120.14(12)
C13 C14 H14 119.9
C9 C14 H14 119.9
S C15 H15A 109.5
S C15 H15B 109.5
H15A C15 H15B 109.5
S C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S O2 1.4897(10)
S C1 1.7646(12)
S C15 1.7922(13)
F1 C4 1.3636(15)
F2 C12 1.3565(15)
O1 C7 1.3773(15)
O1 C8 1.3773(15)
C1 C8 1.3645(17)
C1 C2 1.4417(17)
C2 C7 1.3946(17)
C2 C3 1.3977(17)
C3 C4 1.3769(19)
C3 H3 0.9500
C4 C5 1.389(2)
C5 C6 1.386(2)
C5 H5 0.9500
C6 C7 1.3820(18)
C6 H6 0.9500
C8 C9 1.4584(17)
C9 C10 1.3966(18)
C9 C14 1.4011(17)
C10 C11 1.3837(18)
C10 H10 0.9500
C11 C12 1.377(2)
C11 H11 0.9500
C12 C13 1.378(2)
C13 C14 1.3835(19)
C13 H13 0.9500
C14 H14 0.9500
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 0.9800
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
_geom_hbond_publ_flag
C14 H14 O2 2_666 0.95 2.54 3.4025(17) 151.2 yes
C15 H15C F2 1_556 0.98 2.52 3.2235(16) 128.7 yes
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 S C1 C8 141.63(11)
C15 S C1 C8 -108.95(12)
O2 S C1 C2 -33.41(12)
C15 S C1 C2 76.01(12)
C8 C1 C2 C7 -0.38(13)
S C1 C2 C7 175.46(9)
C8 C1 C2 C3 179.48(14)
S C1 C2 C3 -4.7(2)
C7 C2 C3 C4 0.23(18)
C1 C2 C3 C4 -179.61(13)
C2 C3 C4 F1 -179.84(11)
C2 C3 C4 C5 0.0(2)
F1 C4 C5 C6 179.82(12)
C3 C4 C5 C6 0.0(2)
C4 C5 C6 C7 -0.2(2)
C8 O1 C7 C6 -179.50(12)
C8 O1 C7 C2 -0.78(13)
C5 C6 C7 O1 178.94(12)
C5 C6 C7 C2 0.4(2)
C3 C2 C7 O1 -179.17(11)
C1 C2 C7 O1 0.72(14)
C3 C2 C7 C6 -0.4(2)
C1 C2 C7 C6 179.46(12)
C2 C1 C8 O1 -0.09(14)
S C1 C8 O1 -175.89(9)
C2 C1 C8 C9 179.81(12)
S C1 C8 C9 4.0(2)
C7 O1 C8 C1 0.53(13)
C7 O1 C8 C9 -179.39(10)
C1 C8 C9 C10 28.3(2)
O1 C8 C9 C10 -151.79(11)
C1 C8 C9 C14 -151.07(14)
O1 C8 C9 C14 28.83(16)
C14 C9 C10 C11 2.31(19)
C8 C9 C10 C11 -177.08(12)
C9 C10 C11 C12 -1.9(2)
C10 C11 C12 F2 -179.66(12)
C10 C11 C12 C13 0.0(2)
F2 C12 C13 C14 -178.91(12)
C11 C12 C13 C14 1.4(2)
C12 C13 C14 C9 -1.0(2)
C10 C9 C14 C13 -0.82(19)
C8 C9 C14 C13 178.58(11)