#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/53/2225343.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_2225343
loop_
_publ_author_name
'Choi, Hong Dae'
'Seo, Pil Ja'
'Son, Byeng Wha'
'Lee, Uk'
_publ_section_title
;
 3-Ethylsulfinyl-2-(4-fluorophenyl)-5-iodo-7-methyl-1-benzofuran
;
_journal_coeditor_code           PB2023
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o629
_journal_paper_doi               10.1107/S1600536810005581
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C17 H14 F I O2 S'
_chemical_formula_moiety         'C17 H14 F I O2 S'
_chemical_formula_sum            'C17 H14 F I O2 S'
_chemical_formula_weight         428.24
_chemical_name_systematic
;
3-Ethylsulfinyl-2-(4-fluorophenyl)-5-iodo-7-methyl-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
_audit_creation_method           'form.cif (version 2.0)'
_cell_angle_alpha                76.2890(10)
_cell_angle_beta                 89.1380(10)
_cell_angle_gamma                74.8020(10)
_cell_formula_units_Z            2
_cell_length_a                   7.4681(5)
_cell_length_b                   10.3023(7)
_cell_length_c                   10.9761(7)
_cell_measurement_reflns_used    6089
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.43
_cell_measurement_theta_min      2.11
_cell_volume                     790.73(9)
_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      273(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Bruker HELIOS graded multilayer optics'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_sigmaI/netI    0.0390
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6867
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.83
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.171
_exptl_absorpt_correction_T_max  0.582
_exptl_absorpt_correction_T_min  0.520
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.799
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.709
_refine_diff_density_min         -0.806
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3386
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0233
_refine_ls_R_factor_gt           0.0222
_refine_ls_shift/esd_max         <0.001
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0284P)²+0.4222P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0577
_refine_ls_wR_factor_ref         0.0587
_reflns_number_gt                3261
_reflns_number_total             3386
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pb2023.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2225343
_cod_database_fobs_code          2225343
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 0.542549(19) 0.247310(13) 1.062688(11) 0.02504(6) Uani d . 1 . .
F F -0.0461(2) 0.7492(2) -0.01911(13) 0.0441(4) Uani d . 1 . .
O O1 0.2937(2) 0.37876(15) 0.50304(13) 0.0214(3) Uani d . 1 . .
O O2 0.3809(2) 0.75140(17) 0.66534(15) 0.0284(3) Uani d . 1 . .
C C1 0.2629(3) 0.5691(2) 0.57785(18) 0.0204(4) Uani d . 1 . .
C C2 0.3398(3) 0.4484(2) 0.67903(19) 0.0201(4) Uani d . 1 . .
C C3 0.3934(3) 0.4255(2) 0.80613(18) 0.0215(4) Uani d . 1 . .
H H3 0.3824 0.4982 0.8447 0.026 Uiso calc R 1 . .
C C4 0.4640(3) 0.2880(2) 0.87108(18) 0.0215(4) Uani d . 1 . .
C C5 0.4839(3) 0.1760(2) 0.8147(2) 0.0243(4) Uani d . 1 . .
H H5 0.5346 0.0861 0.8620 0.029 Uiso calc R 1 . .
C C6 0.4289(3) 0.1976(2) 0.68911(19) 0.0217(4) Uani d . 1 . .
C C7 0.3574(3) 0.3354(2) 0.62726(18) 0.0205(4) Uani d . 1 . .
C C8 0.2388(3) 0.5210(2) 0.47433(19) 0.0205(4) Uani d . 1 . .
C C9 0.1667(3) 0.5850(2) 0.34449(19) 0.0219(4) Uani d . 1 . .
C C10 0.0601(3) 0.7217(3) 0.3068(2) 0.0284(5) Uani d . 1 . .
H H10 0.0353 0.7757 0.3652 0.034 Uiso calc R 1 . .
C C11 -0.0100(3) 0.7790(3) 0.1840(2) 0.0313(5) Uani d . 1 . .
H H11 -0.0791 0.8710 0.1587 0.038 Uiso calc R 1 . .
C C12 0.0261(3) 0.6952(3) 0.1005(2) 0.0298(5) Uani d . 1 . .
C C13 0.1322(3) 0.5599(3) 0.1329(2) 0.0303(5) Uani d . 1 . .
H H13 0.1545 0.5065 0.0740 0.036 Uiso calc R 1 . .
C C14 0.2052(3) 0.5048(2) 0.2553(2) 0.0259(4) Uani d . 1 . .
H H14 0.2799 0.4142 0.2785 0.031 Uiso calc R 1 . .
C C15 0.4396(4) 0.0826(2) 0.6251(2) 0.0295(5) Uani d . 1 . .
H H15A 0.3163 0.0779 0.6072 0.044 Uiso calc R 1 . .
H H15B 0.5075 -0.0038 0.6791 0.044 Uiso calc R 1 . .
H H15C 0.5018 0.0999 0.5482 0.044 Uiso calc R 1 . .
C C16 0.0218(3) 0.7605(2) 0.6731(2) 0.0279(4) Uani d . 1 . .
H H16A -0.0783 0.7464 0.6269 0.034 Uiso calc R 1 . .
H H16B 0.0467 0.6908 0.7520 0.034 Uiso calc R 1 . .
C C17 -0.0346(4) 0.9043(3) 0.6981(2) 0.0383(6) Uani d . 1 . .
H H17A 0.0664 0.9186 0.7417 0.057 Uiso calc R 1 . .
H H17B -0.1411 0.9124 0.7486 0.057 Uiso calc R 1 . .
H H17C -0.0646 0.9727 0.6198 0.057 Uiso calc R 1 . .
S S1 0.22856(8) 0.74390(5) 0.58266(4) 0.02169(11) Uani d . 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 . 2_667 168.75(7) ?
C8 O1 C7 . . 106.96(15) ?
C8 C1 C2 . . 106.76(18) ?
C8 C1 S1 . . 126.56(16) ?
C2 C1 S1 . . 126.41(15) ?
C7 C2 C3 . . 119.10(19) ?
C7 C2 C1 . . 105.34(17) ?
C3 C2 C1 . . 135.56(19) ?
C4 C3 C2 . . 116.33(18) ?
C4 C3 H3 . . 121.8 ?
C2 C3 H3 . . 121.8 ?
C3 C4 C5 . . 123.00(18) ?
C3 C4 I . . 117.95(15) ?
C5 C4 I . . 119.06(15) ?
C6 C5 C4 . . 121.11(19) ?
C6 C5 H5 . . 119.4 ?
C4 C5 H5 . . 119.4 ?
C7 C6 C5 . . 114.58(18) ?
C7 C6 C15 . . 121.77(18) ?
C5 C6 C15 . . 123.63(19) ?
O1 C7 C6 . . 123.70(18) ?
O1 C7 C2 . . 110.45(18) ?
C6 C7 C2 . . 125.85(18) ?
O1 C8 C1 . . 110.48(17) ?
O1 C8 C9 . . 114.21(17) ?
C1 C8 C9 . . 135.31(19) ?
C10 C9 C14 . . 118.92(19) ?
C10 C9 C8 . . 122.32(19) ?
C14 C9 C8 . . 118.8(2) ?
C11 C10 C9 . . 121.3(2) ?
C11 C10 H10 . . 119.4 ?
C9 C10 H10 . . 119.4 ?
C12 C11 C10 . . 117.9(2) ?
C12 C11 H11 . . 121.1 ?
C10 C11 H11 . . 121.1 ?
F C12 C13 . . 118.6(2) ?
F C12 C11 . . 118.3(2) ?
C13 C12 C11 . . 123.0(2) ?
C12 C13 C14 . . 118.5(2) ?
C12 C13 H13 . . 120.7 ?
C14 C13 H13 . . 120.7 ?
C13 C14 C9 . . 120.4(2) ?
C13 C14 H14 . . 119.8 ?
C9 C14 H14 . . 119.8 ?
C6 C15 H15A . . 109.5 ?
C6 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C6 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C17 C16 S1 . . 109.14(18) ?
C17 C16 H16A . . 109.9 ?
S1 C16 H16A . . 109.9 ?
C17 C16 H16B . . 109.9 ?
S1 C16 H16B . . 109.9 ?
H16A C16 H16B . . 108.3 ?
C16 C17 H17A . . 109.5 ?
C16 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C16 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
O2 S1 C1 . . 107.96(10) ?
O2 S1 C16 . . 106.52(10) ?
C1 S1 C16 . . 97.83(11) ?
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 . 2.106(2) ?
I O2 2_667 3.052(2) ?
F C12 . 1.357(2) ?
O1 C8 . 1.373(2) ?
O1 C7 . 1.380(2) ?
O2 S1 . 1.495(2) ?
C1 C8 . 1.374(3) ?
C1 C2 . 1.449(3) ?
C1 S1 . 1.765(2) ?
C2 C7 . 1.389(3) ?
C2 C3 . 1.405(3) ?
C3 C4 . 1.391(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.407(3) ?
C5 C6 . 1.394(3) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.385(3) ?
C6 C15 . 1.499(3) ?
C8 C9 . 1.465(3) ?
C9 C10 . 1.391(3) ?
C9 C14 . 1.405(3) ?
C10 C11 . 1.387(3) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.380(4) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.376(4) ?
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 ?
C16 C17 . 1.520(3) ?
C16 S1 . 1.815(2) ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
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
C8 C1 C2 C7 . . . . 0.4(2) ?
S1 C1 C2 C7 . . . . -173.92(16) ?
C8 C1 C2 C3 . . . . -179.2(2) ?
S1 C1 C2 C3 . . . . 6.5(4) ?
C7 C2 C3 C4 . . . . 0.9(3) ?
C1 C2 C3 C4 . . . . -179.6(2) ?
C2 C3 C4 C5 . . . . 0.6(3) ?
C2 C3 C4 I . . . . -179.02(15) ?
C3 C4 C5 C6 . . . . -1.5(4) ?
I C4 C5 C6 . . . . 178.17(17) ?
C4 C5 C6 C7 . . . . 0.7(3) ?
C4 C5 C6 C15 . . . . -177.5(2) ?
C8 O1 C7 C6 . . . . -178.4(2) ?
C8 O1 C7 C2 . . . . 1.4(2) ?
C5 C6 C7 O1 . . . . -179.43(19) ?
C15 C6 C7 O1 . . . . -1.2(3) ?
C5 C6 C7 C2 . . . . 0.9(3) ?
C15 C6 C7 C2 . . . . 179.1(2) ?
C3 C2 C7 O1 . . . . 178.56(18) ?
C1 C2 C7 O1 . . . . -1.1(2) ?
C3 C2 C7 C6 . . . . -1.7(3) ?
C1 C2 C7 C6 . . . . 178.6(2) ?
C7 O1 C8 C1 . . . . -1.1(2) ?
C7 O1 C8 C9 . . . . 179.96(18) ?
C2 C1 C8 O1 . . . . 0.4(2) ?
S1 C1 C8 O1 . . . . 174.74(15) ?
C2 C1 C8 C9 . . . . 179.1(2) ?
S1 C1 C8 C9 . . . . -6.6(4) ?
O1 C8 C9 C10 . . . . 162.3(2) ?
C1 C8 C9 C10 . . . . -16.3(4) ?
O1 C8 C9 C14 . . . . -17.0(3) ?
C1 C8 C9 C14 . . . . 164.4(2) ?
C14 C9 C10 C11 . . . . 0.7(4) ?
C8 C9 C10 C11 . . . . -178.6(2) ?
C9 C10 C11 C12 . . . . 1.3(4) ?
C10 C11 C12 F . . . . 178.2(2) ?
C10 C11 C12 C13 . . . . -2.0(4) ?
F C12 C13 C14 . . . . -179.7(2) ?
C11 C12 C13 C14 . . . . 0.5(4) ?
C12 C13 C14 C9 . . . . 1.7(4) ?
C10 C9 C14 C13 . . . . -2.3(3) ?
C8 C9 C14 C13 . . . . 177.1(2) ?
C8 C1 S1 O2 . . . . -139.72(19) ?
C2 C1 S1 O2 . . . . 33.5(2) ?
C8 C1 S1 C16 . . . . 110.0(2) ?
C2 C1 S1 C16 . . . . -76.8(2) ?
C17 C16 S1 O2 . . . . 65.53(18) ?
C17 C16 S1 C1 . . . . 176.96(16) ?
