#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/99/2239920.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_2239920
loop_
_publ_author_name
'Choi, Hong Dae'
'Lee, Uk'
_publ_section_title
;
 Crystal structure of
 5-iodo-2-methyl-3-[(4-methylphenyl)sulfonyl]-1-benzofuran
;
_journal_coeditor_code           HB7273
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1028
_journal_paper_doi               10.1107/S1600536814018510
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C16 H13 I O3 S'
_chemical_formula_moiety         'C16 H13 I O3 S'
_chemical_formula_sum            'C16 H13 I O3 S'
_chemical_formula_weight         412.22
_chemical_melting_point_gt       462
_chemical_melting_point_lt       461
_chemical_name_systematic
;
5-iodo-2-methyl-3-[(4-methylphenyl)sulfonyl]-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                111.5400(10)
_cell_angle_beta                 90.8820(10)
_cell_angle_gamma                108.7600(10)
_cell_formula_units_Z            2
_cell_length_a                   7.21610(10)
_cell_length_b                   10.5267(2)
_cell_length_c                   11.3442(2)
_cell_measurement_reflns_used    9550
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.37
_cell_measurement_theta_min      3.02
_cell_volume                     750.20(2)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) 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 0.990
_diffrn_measured_fraction_theta_max 0.990
_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  0.0274
_diffrn_reflns_av_sigmaI/netI    0.0228
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13690
_diffrn_reflns_theta_full        28.39
_diffrn_reflns_theta_max         28.39
_diffrn_reflns_theta_min         1.95
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.280
_exptl_absorpt_correction_T_max  0.5200
_exptl_absorpt_correction_T_min  0.4269
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.825
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.33
_refine_diff_density_max         0.531
_refine_diff_density_min         -0.821
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3730
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0252
_refine_ls_R_factor_gt           0.0233
_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)+(0.0251P)²+0.4508P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0583
_refine_ls_wR_factor_ref         0.0594
_reflns_number_gt                3508
_reflns_number_total             3730
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb7273sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        750.19(2)
_cod_original_sg_symbol_Hall     '-P 1 '
_cod_database_code               2239920
_cod_database_fobs_code          2239920
#BEGIN Tags that were not found in dictionaries:
#END Tags that were not found in dictionaries
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_symmetry_multiplicity
I I1 0.34881(2) 0.005191(17) 0.133697(13) 0.03924(6) Uani d . 1 2
S S1 0.51630(7) 0.39711(5) 0.72563(4) 0.02485(10) Uani d . 1 2
O O1 0.1860(2) -0.00618(16) 0.66250(15) 0.0303(3) Uani d . 1 2
O O2 0.6298(2) 0.41551(16) 0.62596(13) 0.0302(3) Uani d . 1 2
O O3 0.6169(2) 0.43950(18) 0.85197(14) 0.0346(3) Uani d . 1 2
C C1 0.3716(3) 0.2132(2) 0.66867(18) 0.0245(4) Uani d . 1 2
C C2 0.3274(3) 0.1121(2) 0.53672(18) 0.0236(4) Uani d . 1 2
C C3 0.3694(3) 0.1210(2) 0.41971(19) 0.0257(4) Uani d . 1 2
H H3 0.4451 0.2108 0.4148 0.031 Uiso calc R 1 2
C C4 0.2959(3) -0.0065(2) 0.31154(19) 0.0283(4) Uani d . 1 2
C C5 0.1880(3) -0.1412(2) 0.3154(2) 0.0329(4) Uani d . 1 2
H H5 0.1444 -0.2267 0.2386 0.040 Uiso calc R 1 2
C C6 0.1449(3) -0.1498(2) 0.4313(2) 0.0326(4) Uani d . 1 2
H H6 0.0707 -0.2398 0.4364 0.039 Uiso calc R 1 2
C C7 0.2144(3) -0.0220(2) 0.5385(2) 0.0268(4) Uani d . 1 2
C C8 0.2817(3) 0.1378(2) 0.7397(2) 0.0281(4) Uani d . 1 2
C C9 0.2619(3) 0.1795(3) 0.8770(2) 0.0365(5) Uani d . 1 2
H H9A 0.3626 0.2751 0.9271 0.055 Uiso calc R 1 2
H H9B 0.2802 0.1066 0.9058 0.055 Uiso calc R 1 2
H H9C 0.1299 0.1844 0.8893 0.055 Uiso calc R 1 2
C C10 0.3497(3) 0.4906(2) 0.73988(18) 0.0248(4) Uani d . 1 2
C C11 0.3006(3) 0.5246(2) 0.63922(19) 0.0288(4) Uani d . 1 2
H H11 0.3530 0.4950 0.5615 0.035 Uiso calc R 1 2
C C12 0.1741(3) 0.6022(2) 0.6538(2) 0.0328(4) Uani d . 1 2
H H12 0.1422 0.6274 0.5858 0.039 Uiso calc R 1 2
C C13 0.0926(3) 0.6441(2) 0.7656(2) 0.0309(4) Uani d . 1 2
C C14 0.1398(3) 0.6056(2) 0.8638(2) 0.0345(5) Uani d . 1 2
H H14 0.0825 0.6315 0.9399 0.041 Uiso calc R 1 2
C C15 0.2688(3) 0.5302(2) 0.85277(19) 0.0317(4) Uani d . 1 2
H H15 0.3016 0.5059 0.9211 0.038 Uiso calc R 1 2
C C16 -0.0386(4) 0.7339(2) 0.7832(3) 0.0412(5) Uani d . 1 2
H H16A 0.0429 0.8378 0.8215 0.062 Uiso calc R 1 2
H H16B -0.1335 0.7112 0.8399 0.062 Uiso calc R 1 2
H H16C -0.1104 0.7110 0.6998 0.062 Uiso calc R 1 2
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'
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_3
_geom_angle
C4 I1 I1 2_655 152.81(5)
O3 S1 O2 . 119.63(9)
O3 S1 C1 . 108.45(10)
O2 S1 C1 . 106.07(9)
O3 S1 C10 . 107.93(10)
O2 S1 C10 . 108.10(9)
C1 S1 C10 . 105.86(9)
C8 O1 C7 . 107.15(15)
C8 C1 C2 . 107.56(17)
C8 C1 S1 . 126.69(16)
C2 C1 S1 . 125.74(14)
C7 C2 C3 . 119.25(18)
C7 C2 C1 . 105.06(17)
C3 C2 C1 . 135.69(17)
C4 C3 C2 . 116.96(18)
C4 C3 H3 . 121.5
C2 C3 H3 . 121.5
C3 C4 C5 . 123.1(2)
C3 C4 I1 . 117.72(15)
C5 C4 I1 . 119.19(15)
C6 C5 C4 . 119.9(2)
C6 C5 H5 . 120.0
C4 C5 H5 . 120.0
C7 C6 C5 . 116.79(19)
C7 C6 H6 . 121.6
C5 C6 H6 . 121.6
C6 C7 O1 . 126.11(18)
C6 C7 C2 . 123.91(19)
O1 C7 C2 . 109.97(17)
C1 C8 O1 . 110.23(18)
C1 C8 C9 . 133.9(2)
O1 C8 C9 . 115.80(17)
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
C11 C10 C15 . 120.7(2)
C11 C10 S1 . 119.87(16)
C15 C10 S1 . 119.40(16)
C12 C11 C10 . 118.98(19)
C12 C11 H11 . 120.5
C10 C11 H11 . 120.5
C11 C12 C13 . 121.5(2)
C11 C12 H12 . 119.3
C13 C12 H12 . 119.3
C12 C13 C14 . 118.5(2)
C12 C13 C16 . 121.3(2)
C14 C13 C16 . 120.1(2)
C15 C14 C13 . 121.3(2)
C15 C14 H14 . 119.4
C13 C14 H14 . 119.4
C14 C15 C10 . 118.99(19)
C14 C15 H15 . 120.5
C10 C15 H15 . 120.5
C13 C16 H16A . 109.5
C13 C16 H16B . 109.5
H16A C16 H16B . 109.5
C13 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
I1 C4 . 2.099(2)
I1 I1 2_655 3.7534(3)
S1 O3 . 1.4389(14)
S1 O2 . 1.4400(14)
S1 C1 . 1.737(2)
S1 C10 . 1.758(2)
O1 C8 . 1.369(3)
O1 C7 . 1.381(3)
C1 C8 . 1.362(3)
C1 C2 . 1.439(3)
C2 C7 . 1.393(3)
C2 C3 . 1.396(3)
C3 C4 . 1.379(3)
C3 H3 . 0.9500
C4 C5 . 1.398(3)
C5 C6 . 1.384(3)
C5 H5 . 0.9500
C6 C7 . 1.374(3)
C6 H6 . 0.9500
C8 C9 . 1.478(3)
C9 H9A . 0.9800
C9 H9B . 0.9800
C9 H9C . 0.9800
C10 C11 . 1.388(3)
C10 C15 . 1.394(3)
C11 C12 . 1.383(3)
C11 H11 . 0.9500
C12 C13 . 1.388(3)
C12 H12 . 0.9500
C13 C14 . 1.389(3)
C13 C16 . 1.507(3)
C14 C15 . 1.384(3)
C14 H14 . 0.9500
C15 H15 . 0.9500
C16 H16A . 0.9800
C16 H16B . 0.9800
C16 H16C . 0.9800
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 H15 O3 2_667 0.95 2.44 3.311(2) 153
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
O3 S1 C1 C8 . 31.6(2)
O2 S1 C1 C8 . 161.28(18)
C10 S1 C1 C8 . -84.0(2)
O3 S1 C1 C2 . -147.56(17)
O2 S1 C1 C2 . -17.9(2)
C10 S1 C1 C2 . 96.83(18)
C8 C1 C2 C7 . -1.5(2)
S1 C1 C2 C7 . 177.78(15)
C8 C1 C2 C3 . 177.9(2)
S1 C1 C2 C3 . -2.8(3)
C7 C2 C3 C4 . -0.5(3)
C1 C2 C3 C4 . -179.8(2)
C2 C3 C4 C5 . -1.6(3)
C2 C3 C4 I1 . 178.02(14)
I1 I1 C4 C3 2_655 89.06(19)
I1 I1 C4 C5 2_655 -91.27(19)
C3 C4 C5 C6 . 2.3(3)
I1 C4 C5 C6 . -177.38(15)
C4 C5 C6 C7 . -0.6(3)
C5 C6 C7 O1 . 179.13(19)
C5 C6 C7 C2 . -1.5(3)
C8 O1 C7 C6 . 179.2(2)
C8 O1 C7 C2 . -0.3(2)
C3 C2 C7 C6 . 2.1(3)
C1 C2 C7 C6 . -178.35(19)
C3 C2 C7 O1 . -178.42(16)
C1 C2 C7 O1 . 1.1(2)
C2 C1 C8 O1 . 1.4(2)
S1 C1 C8 O1 . -177.87(14)
C2 C1 C8 C9 . -176.3(2)
S1 C1 C8 C9 . 4.4(4)
C7 O1 C8 C1 . -0.7(2)
C7 O1 C8 C9 . 177.42(17)
O3 S1 C10 C11 . 151.02(16)
O2 S1 C10 C11 . 20.28(18)
C1 S1 C10 C11 . -93.02(17)
O3 S1 C10 C15 . -28.79(18)
O2 S1 C10 C15 . -159.52(15)
C1 S1 C10 C15 . 87.17(17)
C15 C10 C11 C12 . 1.8(3)
S1 C10 C11 C12 . -178.00(15)
C10 C11 C12 C13 . -1.3(3)
C11 C12 C13 C14 . -0.4(3)
C11 C12 C13 C16 . 177.49(19)
C12 C13 C14 C15 . 1.5(3)
C16 C13 C14 C15 . -176.3(2)
C13 C14 C15 C10 . -1.0(3)
C11 C10 C15 C14 . -0.7(3)
S1 C10 C15 C14 . 179.13(16)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139086898
