#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/58/2225824.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_2225824
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-1-benzofuran
;
_journal_coeditor_code           DS2026
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1043
_journal_paper_doi               10.1107/S1600536810012717
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C16 H12 F I O2 S'
_chemical_formula_moiety         'C16 H12 F I O2 S'
_chemical_formula_sum            'C16 H12 F I O2 S'
_chemical_formula_weight         414.22
_chemical_name_systematic
;
3-Ethylsulfinyl-2-(4-fluorophenyl)-5-iodo-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                100.637(2)
_cell_angle_beta                 97.947(2)
_cell_angle_gamma                105.086(2)
_cell_formula_units_Z            2
_cell_length_a                   7.2942(4)
_cell_length_b                   9.6312(5)
_cell_length_c                   11.0132(6)
_cell_measurement_reflns_used    9908
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.59
_cell_measurement_theta_min      2.60
_cell_volume                     719.91(7)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0292
_diffrn_reflns_av_sigmaI/netI    0.0226
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_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            12738
_diffrn_reflns_theta_full        27.59
_diffrn_reflns_theta_max         27.59
_diffrn_reflns_theta_min         1.92
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.381
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5475
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.911
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.375
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.111
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.630
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3342
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0200
_refine_ls_R_factor_gt           0.0194
_refine_ls_shift/esd_max         0.000
_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
'calc w=1/[σ²(Fo²)+(0.0269P)²+0.2687P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0516
_refine_ls_wR_factor_ref         0.0520
_reflns_number_gt                3237
_reflns_number_total             3342
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ds2026.cif
_cod_data_source_block           I
_cod_database_code               2225824
_cod_database_fobs_code          2225824
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 0.226555(16) 0.736460(12) 1.062556(10) 0.02602(5) Uani d . 1 . .
S S 0.04077(6) 0.19740(5) 0.59260(4) 0.02146(9) Uani d . 1 . .
F F 0.23547(19) 0.15061(15) -0.01197(11) 0.0389(3) Uani d . 1 . .
O O1 0.29054(17) 0.57530(13) 0.50405(11) 0.0205(2) Uani d . 1 . .
O O2 -0.0999(2) 0.20821(16) 0.67760(14) 0.0322(3) Uani d . 1 . .
C C1 0.1561(2) 0.37895(18) 0.57995(16) 0.0197(3) Uani d . 1 . .
C C2 0.2016(2) 0.51016(18) 0.68023(16) 0.0190(3) Uani d . 1 . .
C C3 0.1835(2) 0.53995(19) 0.80655(16) 0.0207(3) Uani d . 1 . .
H H3 0.1287 0.4630 0.8455 0.025 Uiso calc R 1 . .
C C4 0.2487(2) 0.68639(19) 0.87246(16) 0.0213(3) Uani d . 1 . .
C C5 0.3272(3) 0.8028(2) 0.81686(18) 0.0246(4) Uani d . 1 . .
H H5 0.3683 0.9018 0.8652 0.030 Uiso calc R 1 . .
C C6 0.3448(3) 0.77340(19) 0.69133(17) 0.0231(3) Uani d . 1 . .
H H6 0.3972 0.8502 0.6517 0.028 Uiso calc R 1 . .
C C7 0.2821(2) 0.62657(18) 0.62715(16) 0.0193(3) Uani d . 1 . .
C C8 0.2123(2) 0.42343(18) 0.47623(16) 0.0189(3) Uani d . 1 . .
C C9 0.2136(2) 0.35025(19) 0.34774(16) 0.0199(3) Uani d . 1 . .
C C10 0.1546(3) 0.1962(2) 0.30668(18) 0.0255(4) Uani d . 1 . .
H H10 0.1113 0.1371 0.3632 0.031 Uiso calc R 1 . .
C C11 0.1583(3) 0.1286(2) 0.18520(19) 0.0290(4) Uani d . 1 . .
H H11 0.1152 0.0240 0.1571 0.035 Uiso calc R 1 . .
C C12 0.2255(3) 0.2160(2) 0.10629(17) 0.0269(4) Uani d . 1 . .
C C13 0.2847(3) 0.3683(2) 0.14173(18) 0.0282(4) Uani d . 1 . .
H H13 0.3299 0.4258 0.0846 0.034 Uiso calc R 1 . .
C C14 0.2767(3) 0.4354(2) 0.26295(17) 0.0252(3) Uani d . 1 . .
H H14 0.3144 0.5402 0.2887 0.030 Uiso calc R 1 . .
C C15 0.2486(3) 0.1670(2) 0.68306(18) 0.0267(4) Uani d . 1 . .
H H15A 0.3105 0.2532 0.7547 0.032 Uiso calc R 1 . .
H H15B 0.2047 0.0789 0.7178 0.032 Uiso calc R 1 . .
C C16 0.3954(3) 0.1442(2) 0.6025(2) 0.0296(4) Uani d . 1 . .
H H16A 0.3359 0.0565 0.5335 0.044 Uiso calc R 1 . .
H H16B 0.5069 0.1304 0.6543 0.044 Uiso calc R 1 . .
H H16C 0.4384 0.2310 0.5676 0.044 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 . 2_567 167.88(5) ?
O2 S C1 . . 107.52(8) ?
O2 S C15 . . 107.08(9) ?
C1 S C15 . . 97.46(8) ?
C7 O1 C8 . . 107.01(13) ?
C8 C1 C2 . . 107.24(14) ?
C8 C1 S . . 127.97(13) ?
C2 C1 S . . 124.75(13) ?
C7 C2 C3 . . 119.36(16) ?
C7 C2 C1 . . 105.00(15) ?
C3 C2 C1 . . 135.64(16) ?
C4 C3 C2 . . 117.18(16) ?
C4 C3 H3 . . 121.4 ?
C2 C3 H3 . . 121.4 ?
C3 C4 C5 . . 122.70(16) ?
C3 C4 I . . 118.59(13) ?
C5 C4 I . . 118.71(13) ?
C6 C5 C4 . . 120.18(16) ?
C6 C5 H5 . . 119.9 ?
C4 C5 H5 . . 119.9 ?
C7 C6 C5 . . 116.55(16) ?
C7 C6 H6 . . 121.7 ?
C5 C6 H6 . . 121.7 ?
O1 C7 C6 . . 125.25(15) ?
O1 C7 C2 . . 110.72(14) ?
C6 C7 C2 . . 124.02(16) ?
C1 C8 O1 . . 110.02(14) ?
C1 C8 C9 . . 135.88(16) ?
O1 C8 C9 . . 114.08(14) ?
C10 C9 C14 . . 118.59(16) ?
C10 C9 C8 . . 121.74(16) ?
C14 C9 C8 . . 119.67(15) ?
C11 C10 C9 . . 121.07(17) ?
C11 C10 H10 . . 119.5 ?
C9 C10 H10 . . 119.5 ?
C12 C11 C10 . . 118.44(17) ?
C12 C11 H11 . . 120.8 ?
C10 C11 H11 . . 120.8 ?
F C12 C11 . . 118.94(17) ?
F C12 C13 . . 118.20(18) ?
C11 C12 C13 . . 122.86(17) ?
C12 C13 C14 . . 118.37(18) ?
C12 C13 H13 . . 120.8 ?
C14 C13 H13 . . 120.8 ?
C13 C14 C9 . . 120.64(17) ?
C13 C14 H14 . . 119.7 ?
C9 C14 H14 . . 119.7 ?
C16 C15 S . . 111.38(13) ?
C16 C15 H15A . . 109.4 ?
S C15 H15A . . 109.4 ?
C16 C15 H15B . . 109.4 ?
S C15 H15B . . 109.4 ?
H15A C15 H15B . . 108.0 ?
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 ?
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 . 2.098(2) ?
I O2 2_567 3.1230(10) ?
S O2 . 1.4920(10) ?
S C1 . 1.772(2) ?
S C15 . 1.816(2) ?
F C12 . 1.358(2) ?
O1 C7 . 1.370(2) ?
O1 C8 . 1.382(2) ?
C1 C8 . 1.369(2) ?
C1 C2 . 1.446(2) ?
C2 C7 . 1.392(2) ?
C2 C3 . 1.399(2) ?
C3 C4 . 1.386(2) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.406(3) ?
C5 C6 . 1.390(3) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.383(2) ?
C6 H6 . 0.9500 ?
C8 C9 . 1.462(2) ?
C9 C10 . 1.399(2) ?
C9 C14 . 1.401(2) ?
C10 C11 . 1.383(3) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.370(3) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.379(3) ?
C13 C14 . 1.388(3) ?
C13 H13 . 0.9500 ?
C14 H14 . 0.9500 ?
C15 C16 . 1.515(3) ?
C15 H15A . 0.9900 ?
C15 H15B . 0.9900 ?
C16 H16A . 0.9800 ?
C16 H16B . 0.9800 ?
C16 H16C . 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 S C1 C8 . . . . -143.28(16) ?
C15 S C1 C8 . . . . 106.12(17) ?
O2 S C1 C2 . . . . 34.22(16) ?
C15 S C1 C2 . . . . -76.38(15) ?
C8 C1 C2 C7 . . . . 0.56(18) ?
S C1 C2 C7 . . . . -177.37(12) ?
C8 C1 C2 C3 . . . . -179.12(18) ?
S C1 C2 C3 . . . . 2.9(3) ?
C7 C2 C3 C4 . . . . -0.2(2) ?
C1 C2 C3 C4 . . . . 179.41(18) ?
C2 C3 C4 C5 . . . . 1.1(2) ?
C2 C3 C4 I . . . . -179.54(12) ?
C3 C4 C5 C6 . . . . -1.0(3) ?
I C4 C5 C6 . . . . 179.69(13) ?
C4 C5 C6 C7 . . . . -0.1(3) ?
C8 O1 C7 C6 . . . . -179.49(16) ?
C8 O1 C7 C2 . . . . 0.71(17) ?
C5 C6 C7 O1 . . . . -178.78(15) ?
C5 C6 C7 C2 . . . . 1.0(3) ?
C3 C2 C7 O1 . . . . 178.96(14) ?
C1 C2 C7 O1 . . . . -0.79(18) ?
C3 C2 C7 C6 . . . . -0.8(2) ?
C1 C2 C7 C6 . . . . 179.41(16) ?
C2 C1 C8 O1 . . . . -0.15(18) ?
S C1 C8 O1 . . . . 177.70(12) ?
C2 C1 C8 C9 . . . . 177.97(17) ?
S C1 C8 C9 . . . . -4.2(3) ?
C7 O1 C8 C1 . . . . -0.33(18) ?
C7 O1 C8 C9 . . . . -178.90(13) ?
C1 C8 C9 C10 . . . . -3.3(3) ?
O1 C8 C9 C10 . . . . 174.74(15) ?
C1 C8 C9 C14 . . . . 177.15(19) ?
O1 C8 C9 C14 . . . . -4.8(2) ?
C14 C9 C10 C11 . . . . 0.1(3) ?
C8 C9 C10 C11 . . . . -179.44(16) ?
C9 C10 C11 C12 . . . . 1.5(3) ?
C10 C11 C12 F . . . . 177.94(16) ?
C10 C11 C12 C13 . . . . -1.8(3) ?
F C12 C13 C14 . . . . -179.32(16) ?
C11 C12 C13 C14 . . . . 0.4(3) ?
C12 C13 C14 C9 . . . . 1.3(3) ?
C10 C9 C14 C13 . . . . -1.5(3) ?
C8 C9 C14 C13 . . . . 178.04(16) ?
O2 S C15 C16 . . . . 176.25(13) ?
C1 S C15 C16 . . . . -72.79(14) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139078771
