#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/63/2226389.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_2226389
loop_
_publ_author_name
'Choi, Hong Dae'
'Seo, Pil Ja'
'Son, Byeng Wha'
'Lee, Uk'
_publ_section_title
;
 3-(4-Fluorophenylsulfinyl)-5-iodo-2-methyl-1-benzofuran
;
_journal_coeditor_code           CS2129
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1876
_journal_paper_doi               10.1107/S1600536810024931
_journal_volume                  66
_journal_year                    2010
_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
;
3-(4-Fluorophenylsulfinyl)-5-iodo-2-methyl-1-benzofuran
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 107.1810(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.1665(4)
_cell_length_b                   11.4338(4)
_cell_length_c                   9.9296(3)
_cell_measurement_reflns_used    8763
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.56
_cell_measurement_theta_min      2.41
_cell_volume                     1428.13(8)
_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      173(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0314
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12825
_diffrn_reflns_theta_full        27.56
_diffrn_reflns_theta_max         27.56
_diffrn_reflns_theta_min         1.62
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.397
_exptl_absorpt_correction_T_max  0.6483
_exptl_absorpt_correction_T_min  0.5649
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.861
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.575
_refine_diff_density_min         -1.562
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3297
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0294
_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)+(0.0381P)²+1.2193P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0755
_refine_ls_wR_factor_ref         0.0772
_reflns_number_gt                2990
_reflns_number_total             3297
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cs2129.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2226389
_cod_database_fobs_code          2226389
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.774810(15) 0.162106(16) 0.53507(2) 0.03259(8) Uani d . 1 . .
S S 0.70499(5) 0.67499(6) 0.22747(6) 0.02368(14) Uani d . 1 . .
F F 0.31812(15) 0.49689(19) 0.3339(2) 0.0480(5) Uani d . 1 . .
O O1 0.94047(15) 0.67042(15) 0.57609(19) 0.0249(4) Uani d . 1 . .
O O2 0.71831(16) 0.60325(19) 0.10757(19) 0.0318(4) Uani d . 1 . .
C C1 0.8028(2) 0.6377(2) 0.3837(2) 0.0213(5) Uani d . 1 . .
C C2 0.82677(18) 0.5281(2) 0.4598(2) 0.0195(5) Uani d . 1 . .
C C3 0.78672(19) 0.4142(2) 0.4425(2) 0.0219(5) Uani d . 1 . .
H H3 0.7309 0.3931 0.3643 0.026 Uiso calc R 1 . .
C C4 0.8338(2) 0.3340(2) 0.5469(3) 0.0233(5) Uani d . 1 . .
C C5 0.9195(2) 0.3625(2) 0.6643(3) 0.0263(5) Uani d . 1 . .
H H5 0.9488 0.3058 0.7318 0.032 Uiso calc R 1 . .
C C6 0.9608(2) 0.4746(2) 0.6804(3) 0.0259(5) Uani d . 1 . .
H H6 1.0184 0.4951 0.7567 0.031 Uiso calc R 1 . .
C C7 0.91229(19) 0.5544(2) 0.5777(2) 0.0214(5) Uani d . 1 . .
C C8 0.8732(2) 0.7187(2) 0.4571(3) 0.0229(5) Uani d . 1 . .
C C9 0.8903(2) 0.8441(2) 0.4345(3) 0.0292(6) Uani d . 1 . .
H H9A 0.8451 0.8675 0.3436 0.044 Uiso calc R 1 . .
H H9B 0.9632 0.8567 0.4387 0.044 Uiso calc R 1 . .
H H9C 0.8735 0.8896 0.5064 0.044 Uiso calc R 1 . .
C C10 0.59180(19) 0.6152(2) 0.2691(2) 0.0226(5) Uani d . 1 . .
C C11 0.5564(2) 0.6657(2) 0.3746(3) 0.0298(6) Uani d . 1 . .
H H11 0.5945 0.7263 0.4293 0.036 Uiso calc R 1 . .
C C12 0.4639(2) 0.6250(3) 0.3973(3) 0.0330(6) Uani d . 1 . .
H H12 0.4393 0.6570 0.4679 0.040 Uiso calc R 1 . .
C C13 0.4092(2) 0.5362(3) 0.3133(3) 0.0310(6) Uani d . 1 . .
C C14 0.4427(2) 0.4850(3) 0.2094(3) 0.0315(6) Uani d . 1 . .
H H14 0.4039 0.4247 0.1549 0.038 Uiso calc R 1 . .
C C15 0.5360(2) 0.5251(2) 0.1870(3) 0.0267(5) Uani d . 1 . .
H H15 0.5607 0.4916 0.1173 0.032 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
C4 I O2 . 4_566 164.42(8) ?
O2 S C1 . . 110.03(12) ?
O2 S C10 . . 105.95(12) ?
C1 S C10 . . 98.44(11) ?
C8 O1 C7 . . 106.94(19) ?
C8 C1 C2 . . 107.5(2) ?
C8 C1 S . . 121.0(2) ?
C2 C1 S . . 131.48(19) ?
C3 C2 C7 . . 119.1(2) ?
C3 C2 C1 . . 136.5(2) ?
C7 C2 C1 . . 104.4(2) ?
C4 C3 C2 . . 117.1(2) ?
C4 C3 H3 . . 121.4 ?
C2 C3 H3 . . 121.4 ?
C3 C4 C5 . . 122.8(2) ?
C3 C4 I . . 120.02(19) ?
C5 C4 I . . 117.21(19) ?
C6 C5 C4 . . 120.3(2) ?
C6 C5 H5 . . 119.9 ?
C4 C5 H5 . . 119.9 ?
C7 C6 C5 . . 116.6(2) ?
C7 C6 H6 . . 121.7 ?
C5 C6 H6 . . 121.7 ?
C6 C7 O1 . . 125.4(2) ?
C6 C7 C2 . . 124.1(2) ?
O1 C7 C2 . . 110.5(2) ?
C1 C8 O1 . . 110.7(2) ?
C1 C8 C9 . . 133.5(2) ?
O1 C8 C9 . . 115.8(2) ?
C8 C9 H9A . . 109.5 ?
C8 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C8 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C15 C10 C11 . . 121.0(3) ?
C15 C10 S . . 118.73(19) ?
C11 C10 S . . 120.1(2) ?
C12 C11 C10 . . 119.3(3) ?
C12 C11 H11 . . 120.3 ?
C10 C11 H11 . . 120.3 ?
C13 C12 C11 . . 118.6(3) ?
C13 C12 H12 . . 120.7 ?
C11 C12 H12 . . 120.7 ?
F C13 C14 . . 118.1(3) ?
F C13 C12 . . 118.9(3) ?
C14 C13 C12 . . 123.0(3) ?
C13 C14 C15 . . 118.5(3) ?
C13 C14 H14 . . 120.8 ?
C15 C14 H14 . . 120.8 ?
C10 C15 C14 . . 119.5(2) ?
C10 C15 H15 . . 120.2 ?
C14 C15 H15 . . 120.2 ?
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 C4 . 2.104(2) ?
I O2 4_566 3.255(2) ?
S O2 . 1.4981(19) ?
S C1 . 1.751(2) ?
S C10 . 1.795(3) ?
F C13 . 1.351(3) ?
O1 C8 . 1.366(3) ?
O1 C7 . 1.379(3) ?
C1 C8 . 1.360(4) ?
C1 C2 . 1.449(3) ?
C2 C3 . 1.396(3) ?
C2 C7 . 1.396(3) ?
C3 C4 . 1.386(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.401(4) ?
C5 C6 . 1.383(4) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.376(4) ?
C6 H6 . 0.9300 ?
C8 C9 . 1.478(4) ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C10 C15 . 1.383(4) ?
C10 C11 . 1.391(4) ?
C11 C12 . 1.383(4) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.375(4) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.368(4) ?
C14 C15 . 1.389(4) ?
C14 H14 . 0.9300 ?
C15 H15 . 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
_geom_hbond_publ_flag
C5 H5 O1 2_746 0.93 2.55 3.472(3) 169.9 y
C9 H9C O2 4_576 0.96 2.53 3.277(3) 134.6 y
