#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/40/2224099.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_2224099
loop_
_publ_author_name
'Choi, Hong Dae'
'Seo, Pil Ja'
'Son, Byeng Wha'
'Lee, Uk'
_publ_section_title
;
 5-Chloro-2-(4-fluorophenyl)-3-methylsulfinyl-1-benzofuran
;
_journal_coeditor_code           ZQ2011
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2649
_journal_paper_doi               10.1107/S1600536809039749
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C15 H10 Cl F O2 S'
_chemical_formula_moiety         'C15 H10 Cl F O2 S'
_chemical_formula_sum            'C15 H10 Cl F O2 S'
_chemical_formula_weight         308.74
_chemical_name_systematic
;
5-Chloro-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                95.6370(10)
_cell_angle_beta                 91.9750(10)
_cell_angle_gamma                112.3720(10)
_cell_formula_units_Z            2
_cell_length_a                   7.8484(2)
_cell_length_b                   8.3176(2)
_cell_length_c                   10.7353(2)
_cell_measurement_reflns_used    8966
_cell_measurement_temperature    151(2)
_cell_measurement_theta_max      27.56
_cell_measurement_theta_min      2.67
_cell_volume                     642.95(3)
_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      151(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'
_diffrn_radiation_monochromator  HELIOS
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_sigmaI/netI    0.0174
_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       -12
_diffrn_reflns_number            11361
_diffrn_reflns_theta_full        27.56
_diffrn_reflns_theta_max         27.56
_diffrn_reflns_theta_min         1.91
_exptl_absorpt_coefficient_mu    0.468
_exptl_absorpt_correction_T_max  0.868
_exptl_absorpt_correction_T_min  0.843
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.365
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2949
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0285
_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
'w=1/[σ²(Fo²)+(0.043P)²+0.2884P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0787
_refine_ls_wR_factor_ref         0.0800
_reflns_number_gt                2799
_reflns_number_total             2949
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zq2011.cif
_cod_data_source_block           I
_cod_database_code               2224099
_cod_database_fobs_code          2224099
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 0.18454(4) 0.20468(4) 0.59366(3) 0.01959(10) Uani d . 1 . .
Cl Cl 0.58536(5) 0.78256(4) 1.01739(3) 0.02696(10) Uani d . 1 . .
F F -0.06796(13) 0.22320(12) -0.01528(8) 0.0373(2) Uani d . 1 . .
O O1 0.33377(12) 0.68122(11) 0.48927(8) 0.01984(19) Uani d . 1 . .
O O2 0.32352(14) 0.18415(13) 0.68194(10) 0.0292(2) Uani d . 1 . .
C C1 0.25897(17) 0.42982(16) 0.57709(11) 0.0182(2) Uani d . 1 . .
C C2 0.36053(17) 0.57316(16) 0.67248(12) 0.0181(2) Uani d . 1 . .
C C3 0.41614(17) 0.58856(17) 0.79952(11) 0.0199(2) Uani d . 1 . .
H H3 0.3880 0.4888 0.8433 0.024 Uiso calc R 1 . .
C C4 0.51439(18) 0.75637(17) 0.85853(12) 0.0210(3) Uani d . 1 . .
C C5 0.55869(18) 0.90590(17) 0.79684(12) 0.0224(3) Uani d . 1 . .
H H5 0.6274 1.0181 0.8415 0.027 Uiso calc R 1 . .
C C6 0.50280(18) 0.89127(17) 0.67078(12) 0.0219(3) Uani d . 1 . .
H H6 0.5305 0.9910 0.6270 0.026 Uiso calc R 1 . .
C C7 0.40473(17) 0.72374(16) 0.61254(11) 0.0184(2) Uani d . 1 . .
C C8 0.24675(17) 0.50143(16) 0.46942(12) 0.0184(2) Uani d . 1 . .
C C9 0.16187(17) 0.42847(17) 0.34289(11) 0.0185(2) Uani d . 1 . .
C C10 0.01060(18) 0.26868(18) 0.32117(12) 0.0221(3) Uani d . 1 . .
H H10 -0.0400 0.2079 0.3902 0.026 Uiso calc R 1 . .
C C11 -0.06688(19) 0.19735(18) 0.20057(13) 0.0247(3) Uani d . 1 . .
H H11 -0.1679 0.0873 0.1854 0.030 Uiso calc R 1 . .
C C12 0.00739(19) 0.29133(19) 0.10332(12) 0.0244(3) Uani d . 1 . .
C C13 0.15404(19) 0.45109(18) 0.12037(12) 0.0242(3) Uani d . 1 . .
H H13 0.2003 0.5126 0.0508 0.029 Uiso calc R 1 . .
C C14 0.23250(18) 0.52006(17) 0.24092(12) 0.0209(3) Uani d . 1 . .
H H14 0.3344 0.6296 0.2547 0.025 Uiso calc R 1 . .
C C15 -0.01001(19) 0.18735(19) 0.68205(14) 0.0275(3) Uani d . 1 . .
H H15A -0.0655 0.0691 0.7067 0.041 Uiso calc R 1 . .
H H15B -0.1017 0.2104 0.6304 0.041 Uiso calc R 1 . .
H H15C 0.0307 0.2731 0.7574 0.041 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'
Cl Cl 0.1484 0.1585 '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 . . 107.25(6) ?
O2 S C15 . . 106.04(7) ?
C4 Cl O2 . 2_667 174.59(5) ?
C1 S C15 . . 97.55(6) ?
C7 O1 C8 . . 106.71(9) ?
C8 C1 C2 . . 106.97(11) ?
C8 C1 S . . 126.78(10) ?
C2 C1 S . . 126.01(9) ?
C7 C2 C3 . . 119.43(11) ?
C7 C2 C1 . . 105.20(11) ?
C3 C2 C1 . . 135.37(12) ?
C4 C3 C2 . . 116.72(12) ?
C4 C3 H3 . . 121.6 ?
C2 C3 H3 . . 121.6 ?
C3 C4 C5 . . 123.13(12) ?
C3 C4 Cl . . 118.45(10) ?
C5 C4 Cl . . 118.42(10) ?
C6 C5 C4 . . 120.34(12) ?
C6 C5 H5 . . 119.8 ?
C4 C5 H5 . . 119.8 ?
C7 C6 C5 . . 116.26(12) ?
C7 C6 H6 . . 121.9 ?
C5 C6 H6 . . 121.9 ?
O1 C7 C6 . . 125.40(11) ?
O1 C7 C2 . . 110.47(11) ?
C6 C7 C2 . . 124.12(12) ?
C1 C8 O1 . . 110.63(11) ?
C1 C8 C9 . . 133.83(12) ?
O1 C8 C9 . . 115.54(11) ?
C10 C9 C14 . . 119.21(11) ?
C10 C9 C8 . . 121.09(11) ?
C14 C9 C8 . . 119.70(11) ?
C11 C10 C9 . . 121.01(12) ?
C11 C10 H10 . . 119.5 ?
C9 C10 H10 . . 119.5 ?
C12 C11 C10 . . 117.77(12) ?
C12 C11 H11 . . 121.1 ?
C10 C11 H11 . . 121.1 ?
F C12 C11 . . 118.33(12) ?
F C12 C13 . . 118.37(12) ?
C11 C12 C13 . . 123.30(12) ?
C12 C13 C14 . . 118.55(12) ?
C12 C13 H13 . . 120.7 ?
C14 C13 H13 . . 120.7 ?
C13 C14 C9 . . 120.13(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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S O2 . 1.4900(10) ?
S C1 . 1.7660(10) ?
S C15 . 1.7920(10) ?
Cl C4 . 1.7420(10) ?
Cl O2 2_667 3.2440(10) ?
F C12 . 1.3580(10) ?
O1 C7 . 1.376(2) ?
O1 C8 . 1.378(2) ?
C1 C8 . 1.368(2) ?
C1 C2 . 1.444(2) ?
C2 C7 . 1.395(2) ?
C2 C3 . 1.396(2) ?
C3 C4 . 1.385(2) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.398(2) ?
C5 C6 . 1.387(2) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.380(2) ?
C6 H6 . 0.9500 ?
C8 C9 . 1.458(2) ?
C9 C10 . 1.396(2) ?
C9 C14 . 1.404(2) ?
C10 C11 . 1.385(2) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.377(2) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.377(2) ?
C13 C14 . 1.383(2) ?
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
C14 H14 O2 2_666 0.95 2.56 3.4287(16) 151.5
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 . . . . 141.61(12) ?
C15 S C1 C8 . . . . -108.94(12) ?
O2 S C1 C2 . . . . -31.99(12) ?
C15 S C1 C2 . . . . 77.46(12) ?
C8 C1 C2 C7 . . . . -0.78(13) ?
S C1 C2 C7 . . . . 173.85(9) ?
C8 C1 C2 C3 . . . . 178.83(14) ?
S C1 C2 C3 . . . . -6.5(2) ?
C7 C2 C3 C4 . . . . -0.26(18) ?
C1 C2 C3 C4 . . . . -179.83(13) ?
C2 C3 C4 C5 . . . . -0.19(19) ?
C2 C3 C4 Cl . . . . 179.52(9) ?
C3 C4 C5 C6 . . . . 0.6(2) ?
Cl C4 C5 C6 . . . . -179.15(10) ?
C4 C5 C6 C7 . . . . -0.44(19) ?
C8 O1 C7 C6 . . . . 179.96(12) ?
C8 O1 C7 C2 . . . . -1.27(13) ?
C5 C6 C7 O1 . . . . 178.59(11) ?
C5 C6 C7 C2 . . . . -0.01(19) ?
C3 C2 C7 O1 . . . . -178.41(11) ?
C1 C2 C7 O1 . . . . 1.27(13) ?
C3 C2 C7 C6 . . . . 0.37(19) ?
C1 C2 C7 C6 . . . . -179.94(12) ?
C2 C1 C8 O1 . . . . 0.03(14) ?
S C1 C8 O1 . . . . -174.55(9) ?
C2 C1 C8 C9 . . . . -179.35(13) ?
S C1 C8 C9 . . . . 6.1(2) ?
C7 O1 C8 C1 . . . . 0.75(13) ?
C7 O1 C8 C9 . . . . -179.75(10) ?
C1 C8 C9 C10 . . . . 26.5(2) ?
O1 C8 C9 C10 . . . . -152.84(12) ?
C1 C8 C9 C14 . . . . -153.67(14) ?
O1 C8 C9 C14 . . . . 26.98(16) ?
C14 C9 C10 C11 . . . . 1.87(19) ?
C8 C9 C10 C11 . . . . -178.31(12) ?
C9 C10 C11 C12 . . . . -1.6(2) ?
C10 C11 C12 F . . . . -179.67(12) ?
C10 C11 C12 C13 . . . . 0.2(2) ?
F C12 C13 C14 . . . . -179.31(12) ?
C11 C12 C13 C14 . . . . 0.8(2) ?
C12 C13 C14 C9 . . . . -0.49(19) ?
C10 C9 C14 C13 . . . . -0.81(19) ?
C8 C9 C14 C13 . . . . 179.37(12) ?
