##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
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##############################################################################
                                             
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
3-Iodo-2-methyl-1-phenylsulfonyl-1H-indole
;
_chemical_name_common     ?
_chemical_formula_moiety     'C15 H12 I N O2 S'
_chemical_formula_sum     'C15 H12 I N O2 S'
_chemical_formula_iupac     'C15 H12 I N O2 S'
_chemical_formula_weight     397.22
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
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'
_cell_length_a     10.7068(3)
_cell_length_b     16.2670(4)
_cell_length_c     8.5147(2)
_cell_angle_alpha     90.00
_cell_angle_beta     104.5400(10)
_cell_angle_gamma     90.00
_cell_volume     1435.49(6)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     8510
_cell_measurement_theta_min     2.5
_cell_measurement_theta_max     30.4
_cell_measurement_temperature     295(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.24
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.838
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     776
_exptl_absorpt_coefficient_mu     2.376
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.5359
_exptl_absorpt_correction_T_max     0.6479
_exptl_special_details
;
;
_diffrn_ambient_temperature     295(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker Kappa APEXII'
_diffrn_measurement_method     'ω and φ'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     21249
_diffrn_reflns_av_R_equivalents     0.0226
_diffrn_reflns_av_sigmaI/netI     0.0213
_diffrn_reflns_theta_min     2.50
_diffrn_reflns_theta_max     32.76
_diffrn_reflns_theta_full     32.76
_diffrn_measured_fraction_theta_max     0.996
_diffrn_measured_fraction_theta_full     0.996
_diffrn_reflns_limit_h_min     -15
_diffrn_reflns_limit_h_max     16
_diffrn_reflns_limit_k_min     -23
_diffrn_reflns_limit_k_max     24
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_limit_l_max     11
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     .
_refine_special_details
;
;
_reflns_number_total     5276
_reflns_number_gt     3696
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0645
_refine_ls_R_factor_gt     0.0430
_refine_ls_wR_factor_gt     0.1286
_refine_ls_wR_factor_ref     0.1437
_refine_ls_goodness_of_fit_ref     1.058
_refine_ls_restrained_S_all     1.058
_refine_ls_number_reflns     5276
_refine_ls_number_parameters     182
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0743P)²+0.9870P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.944
_refine_diff_density_min     -1.562
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'APEX2 (Bruker, 2004)'
_computing_cell_refinement     'SAINT (Bruker, 2004)'
_computing_data_reduction     'SAINT (Bruker, 2004)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'PLATON (Spek, 2009)'
_computing_publication_material     'SHELXL97 (Sheldrick, 2008)'
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 . .
_geom_special_details
;
;
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_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_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_
    _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
data_global
_journal_date_recd_electronic     2011-01-31
_journal_date_accepted     2011-02-07
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2011
_journal_volume     67
_journal_issue      3
_journal_page_first     o632
_journal_page_last     o632
_journal_paper_category     QO
_journal_coeditor_code     GK2346
_publ_contact_author_name     'V. Manivannan'
_publ_contact_author_address
;
Department of Research and Development,
PRIST University,
Vallam,
Thanjavur - 613 403,
Tamil Nadu,
India.
;
_publ_contact_author_email
                  'crystallography2010@gmail.com, chakkaravarthi_2005@yahoo.com'
_publ_contact_author_fax     ?
_publ_contact_author_phone     '04362-241324'
_publ_section_title
;
3-Iodo-2-methyl-1-phenylsulfonyl-1H-indole
;
loop_
    _publ_author_name
    _publ_author_address
    'C. Ramathilagam '
;
Department of Physics
AMET University
Kanathur, Chennai 603 112
India
;
    'Velu Saravanan'
;
Department of Organic Chemistry
University of Madras
Guindy Campus, Chennai 600 025
India
;
    'A. K. Mohanakrishnan'
;
Department of Organic Chemistry
University of Madras
Guindy Campus, Chennai 600 025
India
;
    'G. Chakkaravarthi'
;
Department of Physics
CPCL Polytechnic College
Chennai 600 068
India
;
    'P. R. Umarani'
;
Department of Physics
Presidency College (Autonomous)
Chennai 600 005
India
;
    'V. Manivannan'
;
Department of Research and Development
PRIST University
Vallam
Thanjavur 613 403
Tamil Nadu
India
;
