#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/93/2229387.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_2229387
loop_
_publ_author_name
'Ramathilagam, C.'
'Saravanan, Velu'
'Mohanakrishnan, A. K.'
'Chakkaravarthi, G.'
'Umarani, P. R.'
'Manivannan, V.'
_publ_section_title
;
 3-Iodo-2-methyl-1-phenylsulfonyl-1H-indole
;
_journal_coeditor_code           GK2346
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o632
_journal_paper_doi               10.1107/S1600536811004685
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C15 H12 I N O2 S'
_chemical_formula_moiety         'C15 H12 I N O2 S'
_chemical_formula_sum            'C15 H12 I N O2 S'
_chemical_formula_weight         397.22
_chemical_name_systematic
;
3-Iodo-2-methyl-1-phenylsulfonyl-1H-indole
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.5400(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.7068(3)
_cell_length_b                   16.2670(4)
_cell_length_c                   8.5147(2)
_cell_measurement_reflns_used    8510
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      30.4
_cell_measurement_theta_min      2.5
_cell_volume                     1435.49(6)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker Kappa APEXII'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_sigmaI/netI    0.0213
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            21249
_diffrn_reflns_theta_full        32.76
_diffrn_reflns_theta_max         32.76
_diffrn_reflns_theta_min         2.50
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.376
_exptl_absorpt_correction_T_max  0.6479
_exptl_absorpt_correction_T_min  0.5359
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.838
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.944
_refine_diff_density_min         -1.562
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         5276
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0430
_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)+(0.0743P)²+0.9870P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1286
_refine_ls_wR_factor_ref         0.1437
_reflns_number_gt                3696
_reflns_number_total             5276
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gk2346.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2229387
_cod_database_fobs_code          2229387
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
C C1 0.8489(3) 0.14775(16) 0.8788(3) 0.0350(5) Uani d . 1 . .
C C2 0.8848(4) 0.0951(2) 1.0097(4) 0.0495(7) Uani d . 1 . .
H H2 0.8265 0.0574 1.0324 0.059 Uiso calc R 1 . .
C C3 1.0098(4) 0.0998(3) 1.1063(5) 0.0638(10) Uani d . 1 . .
H H3 1.0365 0.0646 1.1944 0.077 Uiso calc R 1 . .
C C4 1.0940(4) 0.1562(3) 1.0722(5) 0.0643(11) Uani d . 1 . .
H H4 1.1778 0.1587 1.1375 0.077 Uiso calc R 1 . .
C C5 1.0569(3) 0.2092(3) 0.9431(5) 0.0556(9) Uani d . 1 . .
H H5 1.1149 0.2478 0.9227 0.067 Uiso calc R 1 . .
C C6 0.9331(3) 0.20492(19) 0.8436(4) 0.0433(6) Uani d . 1 . .
H H6 0.9073 0.2398 0.7549 0.052 Uiso calc R 1 . .
C C7 0.7397(3) 0.04833(16) 0.5161(3) 0.0329(5) Uani d . 1 . .
C C8 0.7262(3) -0.03190(16) 0.4724(3) 0.0336(5) Uani d U 1 . .
C C9 0.6619(2) -0.07527(14) 0.5739(3) 0.0297(4) Uani d . 1 . .
C C10 0.6230(3) -0.15718(17) 0.5777(4) 0.0387(6) Uani d . 1 . .
H H10 0.6379 -0.1950 0.5025 0.046 Uiso calc R 1 . .
C C11 0.5626(3) -0.1805(2) 0.6940(4) 0.0478(7) Uani d . 1 . .
H H11 0.5362 -0.2348 0.6978 0.057 Uiso calc R 1 . .
C C12 0.5402(3) -0.1249(2) 0.8061(4) 0.0486(7) Uani d . 1 . .
H H12 0.5005 -0.1429 0.8852 0.058 Uiso calc R 1 . .
C C13 0.5753(3) -0.0428(2) 0.8043(4) 0.0435(6) Uani d . 1 . .
H H13 0.5585 -0.0055 0.8792 0.052 Uiso calc R 1 . .
C C14 0.6367(2) -0.01869(15) 0.6857(3) 0.0309(5) Uani d . 1 . .
C C15 0.7993(4) 0.1168(2) 0.4432(5) 0.0509(7) Uani d . 1 . .
H H15A 0.8230 0.0972 0.3483 0.076 Uiso calc R 1 . .
H H15B 0.8748 0.1362 0.5208 0.076 Uiso calc R 1 . .
H H15C 0.7383 0.1609 0.4137 0.076 Uiso calc R 1 . .
N N1 0.6822(2) 0.05838(13) 0.6481(3) 0.0335(4) Uani d . 1 . .
O O1 0.6046(2) 0.13114(15) 0.8577(4) 0.0552(6) Uani d . 1 . .
O O2 0.6719(2) 0.21172(13) 0.6496(3) 0.0533(6) Uani d . 1 . .
S S1 0.68958(6) 0.14402(4) 0.75748(10) 0.03797(16) Uani d . 1 . .
I I1 0.78752(3) -0.084909(16) 0.28650(3) 0.06383(12) Uani d U 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'
N N 0.0061 0.0033 '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_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 C1 C2 . . 121.9(3) ?
C6 C1 S1 . . 119.1(2) ?
C2 C1 S1 . . 119.0(2) ?
C1 C2 C3 . . 118.5(4) ?
C1 C2 H2 . . 120.8 ?
C3 C2 H2 . . 120.8 ?
C4 C3 C2 . . 120.0(4) ?
C4 C3 H3 . . 120.0 ?
C2 C3 H3 . . 120.0 ?
C3 C4 C5 . . 121.1(3) ?
C3 C4 H4 . . 119.4 ?
C5 C4 H4 . . 119.4 ?
C4 C5 C6 . . 119.9(4) ?
C4 C5 H5 . . 120.0 ?
C6 C5 H5 . . 120.0 ?
C1 C6 C5 . . 118.6(3) ?
C1 C6 H6 . . 120.7 ?
C5 C6 H6 . . 120.7 ?
C8 C7 N1 . . 106.9(2) ?
C8 C7 C15 . . 129.1(3) ?
N1 C7 C15 . . 123.9(3) ?
C7 C8 C9 . . 110.2(2) ?
C7 C8 I1 . . 125.8(2) ?
C9 C8 I1 . . 124.00(18) ?
C14 C9 C10 . . 120.1(2) ?
C14 C9 C8 . . 107.1(2) ?
C10 C9 C8 . . 132.8(3) ?
C11 C10 C9 . . 118.7(3) ?
C11 C10 H10 . . 120.7 ?
C9 C10 H10 . . 120.7 ?
C10 C11 C12 . . 121.0(3) ?
C10 C11 H11 . . 119.5 ?
C12 C11 H11 . . 119.5 ?
C11 C12 C13 . . 122.0(3) ?
C11 C12 H12 . . 119.0 ?
C13 C12 H12 . . 119.0 ?
C12 C13 C14 . . 117.2(3) ?
C12 C13 H13 . . 121.4 ?
C14 C13 H13 . . 121.4 ?
C13 C14 C9 . . 121.0(2) ?
C13 C14 N1 . . 132.0(3) ?
C9 C14 N1 . . 107.0(2) ?
C7 C15 H15A . . 109.5 ?
C7 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C7 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C14 N1 C7 . . 108.7(2) ?
C14 N1 S1 . . 125.89(19) ?
C7 N1 S1 . . 124.72(18) ?
O1 S1 O2 . . 120.43(16) ?
O1 S1 N1 . . 105.47(13) ?
O2 S1 N1 . . 107.93(14) ?
O1 S1 C1 . . 109.09(15) ?
O2 S1 C1 . . 107.83(14) ?
N1 S1 C1 . . 105.06(12) ?
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
C1 C6 . 1.380(4) ?
C1 C2 . 1.381(4) ?
C1 S1 . 1.759(3) ?
C2 C3 . 1.386(6) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.367(7) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.375(6) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.384(5) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 C8 . 1.355(4) ?
C7 N1 . 1.420(3) ?
C7 C15 . 1.493(4) ?
C8 C9 . 1.421(4) ?
C8 I1 . 2.050(3) ?
C9 C14 . 1.399(4) ?
C9 C10 . 1.399(3) ?
C10 C11 . 1.365(5) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.379(5) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.387(5) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.392(4) ?
C13 H13 . 0.9300 ?
C14 N1 . 1.411(3) ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
N1 S1 . 1.667(2) ?
O1 S1 . 1.411(3) ?
O2 S1 . 1.416(3) ?
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
C13 H13 O1 . 0.93 2.29 2.871(4) 120 y
C4 H4 Cg3 3_757 0.93 2.65 3.517(5) 156 y
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
C6 C1 C2 C3 . . . . -0.7(5) ?
S1 C1 C2 C3 . . . . -178.7(3) ?
C1 C2 C3 C4 . . . . 0.7(6) ?
C2 C3 C4 C5 . . . . 0.3(6) ?
C3 C4 C5 C6 . . . . -1.1(6) ?
C2 C1 C6 C5 . . . . -0.1(5) ?
S1 C1 C6 C5 . . . . 177.9(2) ?
C4 C5 C6 C1 . . . . 1.0(5) ?
N1 C7 C8 C9 . . . . -0.5(3) ?
C15 C7 C8 C9 . . . . -179.2(3) ?
N1 C7 C8 I1 . . . . 179.13(18) ?
C15 C7 C8 I1 . . . . 0.5(5) ?
C7 C8 C9 C14 . . . . -0.7(3) ?
I1 C8 C9 C14 . . . . 179.62(18) ?
C7 C8 C9 C10 . . . . 178.6(3) ?
I1 C8 C9 C10 . . . . -1.1(4) ?
C14 C9 C10 C11 . . . . -1.3(4) ?
C8 C9 C10 C11 . . . . 179.5(3) ?
C9 C10 C11 C12 . . . . 0.0(5) ?
C10 C11 C12 C13 . . . . 1.3(5) ?
C11 C12 C13 C14 . . . . -1.1(5) ?
C12 C13 C14 C9 . . . . -0.2(4) ?
C12 C13 C14 N1 . . . . 178.7(3) ?
C10 C9 C14 C13 . . . . 1.4(4) ?
C8 C9 C14 C13 . . . . -179.2(3) ?
C10 C9 C14 N1 . . . . -177.8(2) ?
C8 C9 C14 N1 . . . . 1.6(3) ?
C13 C14 N1 C7 . . . . 179.0(3) ?
C9 C14 N1 C7 . . . . -2.0(3) ?
C13 C14 N1 S1 . . . . 8.1(4) ?
C9 C14 N1 S1 . . . . -172.91(19) ?
C8 C7 N1 C14 . . . . 1.6(3) ?
C15 C7 N1 C14 . . . . -179.7(3) ?
C8 C7 N1 S1 . . . . 172.6(2) ?
C15 C7 N1 S1 . . . . -8.7(4) ?
C14 N1 S1 O1 . . . . -19.0(3) ?
C7 N1 S1 O1 . . . . 171.5(2) ?
C14 N1 S1 O2 . . . . -149.0(2) ?
C7 N1 S1 O2 . . . . 41.5(3) ?
C14 N1 S1 C1 . . . . 96.2(2) ?
C7 N1 S1 C1 . . . . -73.3(2) ?
C6 C1 S1 O1 . . . . -139.6(2) ?
C2 C1 S1 O1 . . . . 38.4(3) ?
C6 C1 S1 O2 . . . . -7.2(3) ?
C2 C1 S1 O2 . . . . 170.8(3) ?
C6 C1 S1 N1 . . . . 107.7(2) ?
C2 C1 S1 N1 . . . . -74.2(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9713300
2 PubChem 11538519
