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#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/85/2228573.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2228573
loop_
_publ_author_name
'Choi, Hong Dae'
'Seo, Pil Ja'
'Son, Byeng Wha'
'Lee, Uk'
_publ_section_title
;
 2-(4-Fluorophenyl)-5-iodo-3-isopropylsulfinyl-1-benzofuran
;
_journal_coeditor_code           SU2229
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3261
_journal_paper_doi               10.1107/S1600536810047665
_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
;
2-(4-Fluorophenyl)-5-iodo-3-isopropylsulfinyl-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                68.6430(10)
_cell_angle_beta                 70.6180(10)
_cell_angle_gamma                89.2410(10)
_cell_formula_units_Z            2
_cell_length_a                   8.43450(10)
_cell_length_b                   9.5874(2)
_cell_length_c                   10.9324(2)
_cell_measurement_reflns_used    9898
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      27.54
_cell_measurement_theta_min      2.30
_cell_volume                     770.83(2)
_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      180(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  0.0275
_diffrn_reflns_av_sigmaI/netI    0.0217
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13711
_diffrn_reflns_theta_full        27.54
_diffrn_reflns_theta_max         27.54
_diffrn_reflns_theta_min         2.14
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.227
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.845
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.233
_exptl_crystal_size_mid          0.216
_exptl_crystal_size_min          0.116
_refine_diff_density_max         0.516
_refine_diff_density_min         -0.930
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3544
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.139
_refine_ls_R_factor_all          0.0213
_refine_ls_R_factor_gt           0.0204
_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/[σ²(Fo²)+(0.0298P)²+0.2380P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0547
_refine_ls_wR_factor_ref         0.0553
_reflns_number_gt                3407
_reflns_number_total             3544
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su2229.cif
_cod_data_source_block           I
_cod_database_code               2228573
_cod_database_fobs_code          2228573
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 I1 0.417391(15) 0.151710(13) 1.131578(12) 0.02794(6) Uani d . 1 . .
S S1 0.35022(6) 0.16149(5) 0.56324(5) 0.02224(10) Uani d . 1 . .
F F1 0.08962(18) 0.68702(15) 0.06579(14) 0.0395(3) Uani d . 1 . .
O O1 0.27453(17) 0.55572(14) 0.60153(14) 0.0241(3) Uani d . 1 . .
O O2 0.46705(19) 0.07898(17) 0.63276(17) 0.0324(3) Uani d . 1 . .
C C1 0.3041(2) 0.3160(2) 0.61705(19) 0.0213(3) Uani d . 1 . .
C C2 0.3257(2) 0.3290(2) 0.7385(2) 0.0213(3) Uani d . 1 . .
C C3 0.3567(2) 0.2321(2) 0.8569(2) 0.0238(4) Uani d . 1 . .
H H3 0.3697 0.1293 0.8716 0.029 Uiso calc R 1 . .
C C4 0.3677(2) 0.2918(2) 0.9521(2) 0.0240(4) Uani d . 1 . .
C C5 0.3511(3) 0.4434(2) 0.9322(2) 0.0279(4) Uani d . 1 . .
H H5 0.3611 0.4801 0.9995 0.034 Uiso calc R 1 . .
C C6 0.3203(3) 0.5403(2) 0.8147(2) 0.0284(4) Uani d . 1 . .
H H6 0.3087 0.6435 0.7991 0.034 Uiso calc R 1 . .
C C7 0.3074(2) 0.4790(2) 0.7221(2) 0.0234(4) Uani d . 1 . .
C C8 0.2727(2) 0.4542(2) 0.5392(2) 0.0216(3) Uani d . 1 . .
C C9 0.2301(2) 0.5145(2) 0.4121(2) 0.0221(4) Uani d . 1 . .
C C10 0.2428(2) 0.6710(2) 0.3413(2) 0.0253(4) Uani d . 1 . .
H H10 0.2834 0.7374 0.3739 0.030 Uiso calc R 1 . .
C C11 0.1966(3) 0.7288(2) 0.2242(2) 0.0290(4) Uani d . 1 . .
H H11 0.2063 0.8348 0.1752 0.035 Uiso calc R 1 . .
C C12 0.1363(2) 0.6309(2) 0.1796(2) 0.0273(4) Uani d . 1 . .
C C13 0.1226(3) 0.4763(2) 0.2458(2) 0.0278(4) Uani d . 1 . .
H H13 0.0818 0.4111 0.2120 0.033 Uiso calc R 1 . .
C C14 0.1698(3) 0.4187(2) 0.3627(2) 0.0264(4) Uani d . 1 . .
H H14 0.1611 0.3125 0.4100 0.032 Uiso calc R 1 . .
C C15 0.1418(2) 0.0465(2) 0.6546(2) 0.0245(4) Uani d . 1 . .
H H15 0.0542 0.1115 0.6309 0.029 Uiso calc R 1 . .
C C16 0.0973(3) -0.0158(3) 0.8118(2) 0.0350(5) Uani d . 1 . .
H H16A -0.0086 -0.0843 0.8568 0.053 Uiso calc R 1 . .
H H16B 0.0833 0.0675 0.8448 0.053 Uiso calc R 1 . .
H H16C 0.1883 -0.0709 0.8359 0.053 Uiso calc R 1 . .
C C17 0.1496(3) -0.0768(2) 0.5953(3) 0.0396(5) Uani d . 1 . .
H H17A 0.2342 -0.1422 0.6187 0.059 Uiso calc R 1 . .
H H17B 0.1811 -0.0299 0.4932 0.059 Uiso calc R 1 . .
H H17C 0.0384 -0.1370 0.6362 0.059 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 I1 O2 . 2_657 170.73(6) ?
O2 S1 C1 . . 106.47(8) ?
O2 S1 C15 . . 107.12(9) ?
C1 S1 C15 . . 99.87(9) ?
C7 O1 C8 . . 106.69(14) ?
C8 C1 C2 . . 106.99(15) ?
C8 C1 S1 . . 126.19(15) ?
C2 C1 S1 . . 125.82(13) ?
C3 C2 C7 . . 118.97(17) ?
C3 C2 C1 . . 135.97(17) ?
C7 C2 C1 . . 105.06(16) ?
C4 C3 C2 . . 117.37(17) ?
C4 C3 H3 . . 121.3 ?
C2 C3 H3 . . 121.3 ?
C3 C4 C5 . . 122.52(18) ?
C3 C4 I1 . . 119.10(14) ?
C5 C4 I1 . . 118.36(14) ?
C6 C5 C4 . . 120.40(18) ?
C6 C5 H5 . . 119.8 ?
C4 C5 H5 . . 119.8 ?
C7 C6 C5 . . 116.43(17) ?
C7 C6 H6 . . 121.8 ?
C5 C6 H6 . . 121.8 ?
O1 C7 C6 . . 125.06(16) ?
O1 C7 C2 . . 110.64(16) ?
C6 C7 C2 . . 124.30(18) ?
C1 C8 O1 . . 110.61(16) ?
C1 C8 C9 . . 134.93(17) ?
O1 C8 C9 . . 114.36(15) ?
C14 C9 C10 . . 119.02(18) ?
C14 C9 C8 . . 121.04(16) ?
C10 C9 C8 . . 119.88(17) ?
C11 C10 C9 . . 120.20(18) ?
C11 C10 H10 . . 119.9 ?
C9 C10 H10 . . 119.9 ?
C12 C11 C10 . . 119.07(18) ?
C12 C11 H11 . . 120.5 ?
C10 C11 H11 . . 120.5 ?
F1 C12 C11 . . 119.27(17) ?
F1 C12 C13 . . 118.10(18) ?
C11 C12 C13 . . 122.63(19) ?
C12 C13 C14 . . 118.15(18) ?
C12 C13 H13 . . 120.9 ?
C14 C13 H13 . . 120.9 ?
C13 C14 C9 . . 120.93(17) ?
C13 C14 H14 . . 119.5 ?
C9 C14 H14 . . 119.5 ?
C16 C15 C17 . . 113.13(17) ?
C16 C15 S1 . . 111.52(14) ?
C17 C15 S1 . . 106.42(14) ?
C16 C15 H15 . . 108.5 ?
C17 C15 H15 . . 108.5 ?
S1 C15 H15 . . 108.5 ?
C15 C16 H16A . . 109.5 ?
C15 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C15 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C15 C17 H17A . . 109.5 ?
C15 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C15 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 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
I1 C4 . 2.1074(19) ?
I1 O2 2_657 3.1525(15) ?
S1 O2 . 1.4876(15) ?
S1 C1 . 1.7774(18) ?
S1 C15 . 1.841(2) ?
F1 C12 . 1.351(2) ?
O1 C7 . 1.373(2) ?
O1 C8 . 1.380(2) ?
C1 C8 . 1.367(3) ?
C1 C2 . 1.446(3) ?
C2 C3 . 1.396(3) ?
C2 C7 . 1.396(2) ?
C3 C4 . 1.385(3) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.402(3) ?
C5 C6 . 1.388(3) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.375(3) ?
C6 H6 . 0.9500 ?
C8 C9 . 1.460(3) ?
C9 C14 . 1.397(3) ?
C9 C10 . 1.402(2) ?
C10 C11 . 1.381(3) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.374(3) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.380(3) ?
C13 C14 . 1.384(3) ?
C13 H13 . 0.9500 ?
C14 H14 . 0.9500 ?
C15 C16 . 1.510(3) ?
C15 C17 . 1.532(3) ?
C15 H15 . 1.0000 ?
C16 H16A . 0.9800 ?
C16 H16B . 0.9800 ?
C16 H16C . 0.9800 ?
C17 H17A . 0.9800 ?
C17 H17B . 0.9800 ?
C17 H17C . 0.9800 ?
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 S1 C1 C8 . . . . 147.63(17) ?
C15 S1 C1 C8 . . . . -101.09(18) ?
O2 S1 C1 C2 . . . . -19.38(18) ?
C15 S1 C1 C2 . . . . 91.91(17) ?
C8 C1 C2 C3 . . . . 178.6(2) ?
S1 C1 C2 C3 . . . . -12.3(3) ?
C8 C1 C2 C7 . . . . -0.9(2) ?
S1 C1 C2 C7 . . . . 168.15(14) ?
C7 C2 C3 C4 . . . . 0.0(3) ?
C1 C2 C3 C4 . . . . -179.5(2) ?
C2 C3 C4 C5 . . . . -0.8(3) ?
C2 C3 C4 I1 . . . . -179.23(13) ?
C3 C4 C5 C6 . . . . 0.9(3) ?
I1 C4 C5 C6 . . . . 179.27(15) ?
C4 C5 C6 C7 . . . . 0.0(3) ?
C8 O1 C7 C6 . . . . 179.81(18) ?
C8 O1 C7 C2 . . . . -0.40(19) ?
C5 C6 C7 O1 . . . . 178.82(18) ?
C5 C6 C7 C2 . . . . -0.9(3) ?
C3 C2 C7 O1 . . . . -178.83(16) ?
C1 C2 C7 O1 . . . . 0.8(2) ?
C3 C2 C7 C6 . . . . 1.0(3) ?
C1 C2 C7 C6 . . . . -179.40(18) ?
C2 C1 C8 O1 . . . . 0.7(2) ?
S1 C1 C8 O1 . . . . -168.30(13) ?
C2 C1 C8 C9 . . . . -175.53(19) ?
S1 C1 C8 C9 . . . . 15.5(3) ?
C7 O1 C8 C1 . . . . -0.2(2) ?
C7 O1 C8 C9 . . . . 176.86(15) ?
C1 C8 C9 C14 . . . . 17.1(3) ?
O1 C8 C9 C14 . . . . -159.09(17) ?
C1 C8 C9 C10 . . . . -165.7(2) ?
O1 C8 C9 C10 . . . . 18.2(2) ?
C14 C9 C10 C11 . . . . -0.2(3) ?
C8 C9 C10 C11 . . . . -177.49(17) ?
C9 C10 C11 C12 . . . . 0.8(3) ?
C10 C11 C12 F1 . . . . 179.47(18) ?
C10 C11 C12 C13 . . . . -1.1(3) ?
F1 C12 C13 C14 . . . . -179.79(18) ?
C11 C12 C13 C14 . . . . 0.8(3) ?
C12 C13 C14 C9 . . . . -0.1(3) ?
C10 C9 C14 C13 . . . . -0.2(3) ?
C8 C9 C14 C13 . . . . 177.14(18) ?
O2 S1 C15 C16 . . . . 43.28(16) ?
C1 S1 C15 C16 . . . . -67.49(15) ?
O2 S1 C15 C17 . . . . -80.53(15) ?
C1 S1 C15 C17 . . . . 168.70(14) ?
