#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/32/2223215.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_2223215
loop_
_publ_author_name
'Choi, Hong Dae'
'Seo, Pil Ja'
'Son, Byeng Wha'
'Lee, Uk'
_publ_section_title
;
 5-Fluoro-2-(4-iodophenyl)-3-methylsulfinyl-1-benzofuran
;
_journal_coeditor_code           VM2001
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2115
_journal_paper_doi               10.1107/S1600536809030992
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C15 H10 F I O2 S'
_chemical_formula_moiety         'C15 H10 F I O2 S'
_chemical_formula_sum            'C15 H10 F I O2 S'
_chemical_formula_weight         400.19
_chemical_name_systematic
;
5-Fluoro-2-(4-iodophenyl)-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                105.5790(10)
_cell_angle_beta                 115.3020(10)
_cell_angle_gamma                101.6710(10)
_cell_formula_units_Z            2
_cell_length_a                   8.8989(5)
_cell_length_b                   9.2370(5)
_cell_length_c                   10.3357(5)
_cell_measurement_reflns_used    4508
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.43
_cell_measurement_theta_min      2.38
_cell_volume                     689.08(6)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_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      273(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0167
_diffrn_reflns_av_sigmaI/netI    0.0251
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5972
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.38
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.484
_exptl_absorpt_correction_T_max  0.784
_exptl_absorpt_correction_T_min  0.650
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2000))'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.929
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.684
_refine_diff_density_min         -0.552
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2957
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0270
_refine_ls_R_factor_gt           0.0223
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_max_lt       0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0248P)²+0.3594P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0519
_refine_ls_wR_factor_ref         0.0546
_reflns_number_gt                2689
_reflns_number_total             2957
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            vm2001.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      P_-1
_cod_database_code               2223215
_cod_database_fobs_code          2223215
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
I I 0.87629(2) 0.09755(2) -0.19147(2) 0.03012(7) Uani d . 1 . .
S S 0.81950(8) 0.77048(7) 0.37848(7) 0.02442(13) Uani d . 1 . .
F F 0.2583(2) 0.7621(2) 0.5294(2) 0.0428(4) Uani d . 1 . .
O O1 0.4384(2) 0.3431(2) 0.1980(2) 0.0233(4) Uani d . 1 . .
O O2 0.8909(3) 0.8594(2) 0.5482(2) 0.0356(4) Uani d . 1 . .
C C1 0.6269(3) 0.6020(3) 0.3101(3) 0.0219(5) Uani d . 1 . .
C C2 0.4906(3) 0.5987(3) 0.3510(3) 0.0222(5) Uani d . 1 . .
C C3 0.4518(3) 0.7126(3) 0.4387(3) 0.0264(5) Uani d . 1 . .
H H3 0.5242 0.8214 0.4904 0.032 Uiso calc R 1 . .
C C4 0.3009(4) 0.6553(3) 0.4443(3) 0.0292(6) Uani d . 1 . .
C C5 0.1882(4) 0.4941(4) 0.3707(3) 0.0310(6) Uani d . 1 . .
H H5 0.0871 0.4634 0.3783 0.037 Uiso calc R 1 . .
C C6 0.2275(3) 0.3798(3) 0.2861(3) 0.0269(5) Uani d . 1 . .
H H6 0.1562 0.2709 0.2367 0.032 Uiso calc R 1 . .
C C7 0.3788(3) 0.4369(3) 0.2791(3) 0.0226(5) Uani d . 1 . .
C C8 0.5907(3) 0.4480(3) 0.2194(3) 0.0220(5) Uani d . 1 . .
C C9 0.6706(3) 0.3730(3) 0.1356(3) 0.0215(5) Uani d . 1 . .
C C10 0.6734(3) 0.2185(3) 0.1215(3) 0.0254(5) Uani d . 1 . .
H H10 0.6323 0.1671 0.1724 0.030 Uiso calc R 1 . .
C C11 0.7365(3) 0.1415(3) 0.0331(3) 0.0262(5) Uani d . 1 . .
H H11 0.7377 0.0389 0.0242 0.031 Uiso calc R 1 . .
C C12 0.7985(3) 0.2194(3) -0.0429(3) 0.0225(5) Uani d . 1 . .
C C13 0.7989(3) 0.3733(3) -0.0283(3) 0.0225(5) Uani d . 1 . .
H H13 0.8410 0.4247 -0.0786 0.027 Uiso calc R 1 . .
C C14 0.7364(3) 0.4501(3) 0.0616(3) 0.0225(5) Uani d . 1 . .
H H14 0.7384 0.5539 0.0725 0.027 Uiso calc R 1 . .
C C15 0.7072(4) 0.8817(3) 0.2787(3) 0.0356(6) Uani d . 1 . .
H H15A 0.6214 0.8998 0.3076 0.053 Uiso calc R 1 . .
H H15B 0.6475 0.8212 0.1679 0.053 Uiso calc R 1 . .
H H15C 0.7929 0.9835 0.3071 0.053 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'
I I -0.4742 1.8119 '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
C12 I O2 . 1_544 165.26(8) ?
O2 S C1 . . 106.61(11) ?
O2 S C15 . . 107.29(13) ?
C1 S C15 . . 97.37(12) ?
C7 O1 C8 . . 106.13(18) ?
C8 C1 C2 . . 107.4(2) ?
C8 C1 S . . 125.10(19) ?
C2 C1 S . . 127.23(18) ?
C7 C2 C3 . . 119.1(2) ?
C7 C2 C1 . . 105.1(2) ?
C3 C2 C1 . . 135.9(2) ?
C4 C3 C2 . . 116.3(2) ?
C4 C3 H3 . . 121.9 ?
C2 C3 H3 . . 121.9 ?
F C4 C3 . . 118.3(2) ?
F C4 C5 . . 117.1(2) ?
C3 C4 C5 . . 124.5(2) ?
C6 C5 C4 . . 119.6(2) ?
C6 C5 H5 . . 120.2 ?
C4 C5 H5 . . 120.2 ?
C7 C6 C5 . . 116.2(2) ?
C7 C6 H6 . . 121.9 ?
C5 C6 H6 . . 121.9 ?
O1 C7 C6 . . 125.1(2) ?
O1 C7 C2 . . 110.6(2) ?
C6 C7 C2 . . 124.3(2) ?
C1 C8 O1 . . 110.7(2) ?
C1 C8 C9 . . 134.3(2) ?
O1 C8 C9 . . 114.9(2) ?
C14 C9 C10 . . 119.0(2) ?
C14 C9 C8 . . 120.6(2) ?
C10 C9 C8 . . 120.3(2) ?
C11 C10 C9 . . 121.0(2) ?
C11 C10 H10 . . 119.5 ?
C9 C10 H10 . . 119.5 ?
C10 C11 C12 . . 119.2(2) ?
C10 C11 H11 . . 120.4 ?
C12 C11 H11 . . 120.4 ?
C13 C12 C11 . . 120.5(2) ?
C13 C12 I . . 119.62(17) ?
C11 C12 I . . 119.79(18) ?
C14 C13 C12 . . 119.9(2) ?
C14 C13 H13 . . 120.1 ?
C12 C13 H13 . . 120.1 ?
C13 C14 C9 . . 120.5(2) ?
C13 C14 H14 . . 119.8 ?
C9 C14 H14 . . 119.8 ?
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
I C12 . 2.098(2) ?
I O2 1_544 3.055(2) ?
S O2 . 1.489(2) ?
S C1 . 1.776(2) ?
S C15 . 1.794(3) ?
F C4 . 1.364(3) ?
O1 C7 . 1.382(3) ?
O1 C8 . 1.386(3) ?
C1 C8 . 1.359(3) ?
C1 C2 . 1.443(3) ?
C2 C7 . 1.395(3) ?
C2 C3 . 1.396(3) ?
C3 C4 . 1.373(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.391(4) ?
C5 C6 . 1.384(4) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.383(3) ?
C6 H6 . 0.9300 ?
C8 C9 . 1.463(3) ?
C9 C14 . 1.394(3) ?
C9 C10 . 1.402(3) ?
C10 C11 . 1.381(4) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.398(3) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.387(3) ?
C13 C14 . 1.387(3) ?
C13 H13 . 0.9300 ?
C14 H14 . 0.9300 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
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
C15 H15C O2 2_776 0.96 2.42 3.238(3) 143.1
C15 H15B Cg3 2_665 0.96 2.91 3.554(3) 125.7
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 . . . . -132.7(2) ?
C15 S C1 C8 . . . . 116.8(2) ?
O2 S C1 C2 . . . . 40.9(2) ?
C15 S C1 C2 . . . . -69.7(2) ?
C8 C1 C2 C7 . . . . 0.0(3) ?
S C1 C2 C7 . . . . -174.51(18) ?
C8 C1 C2 C3 . . . . -179.9(3) ?
S C1 C2 C3 . . . . 5.6(4) ?
C7 C2 C3 C4 . . . . -1.4(3) ?
C1 C2 C3 C4 . . . . 178.5(3) ?
C2 C3 C4 F . . . . 179.6(2) ?
C2 C3 C4 C5 . . . . 0.5(4) ?
F C4 C5 C6 . . . . -178.4(2) ?
C3 C4 C5 C6 . . . . 0.7(4) ?
C4 C5 C6 C7 . . . . -1.0(4) ?
C8 O1 C7 C6 . . . . 178.8(2) ?
C8 O1 C7 C2 . . . . 0.0(2) ?
C5 C6 C7 O1 . . . . -178.5(2) ?
C5 C6 C7 C2 . . . . 0.1(4) ?
C3 C2 C7 O1 . . . . 179.9(2) ?
C1 C2 C7 O1 . . . . 0.0(3) ?
C3 C2 C7 C6 . . . . 1.1(4) ?
C1 C2 C7 C6 . . . . -178.8(2) ?
C2 C1 C8 O1 . . . . 0.0(3) ?
S C1 C8 O1 . . . . 174.65(16) ?
C2 C1 C8 C9 . . . . 176.3(3) ?
S C1 C8 C9 . . . . -9.1(4) ?
C7 O1 C8 C1 . . . . 0.0(3) ?
C7 O1 C8 C9 . . . . -177.1(2) ?
C1 C8 C9 C14 . . . . -37.3(4) ?
O1 C8 C9 C14 . . . . 138.8(2) ?
C1 C8 C9 C10 . . . . 146.1(3) ?
O1 C8 C9 C10 . . . . -37.8(3) ?
C14 C9 C10 C11 . . . . -1.4(4) ?
C8 C9 C10 C11 . . . . 175.2(2) ?
C9 C10 C11 C12 . . . . 0.1(4) ?
C10 C11 C12 C13 . . . . 0.8(4) ?
C10 C11 C12 I . . . . -175.29(19) ?
O2 I C12 C13 1_544 . . . -117.3(3) ?
O2 I C12 C11 1_544 . . . 58.8(4) ?
C11 C12 C13 C14 . . . . -0.4(4) ?
I C12 C13 C14 . . . . 175.70(18) ?
C12 C13 C14 C9 . . . . -1.0(4) ?
C10 C9 C14 C13 . . . . 1.8(4) ?
C8 C9 C14 C13 . . . . -174.8(2) ?
