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###        Electronic paper (Acta Crystallographica Section E)             ###
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#                                                                            #
# 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 2.1.    #
#                                                                            #
# 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/  #
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#            Copyright International Union of Crystallography                #
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data_global
_audit_creation_method     CRYSTALS_ver_12.84
_journal_date_recd_electronic     2006-12-18
_journal_date_accepted     2007-01-05
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue      2
_journal_page_first     o671
_journal_page_last     o672
_journal_paper_category     EO
_journal_coeditor_code     FL2087
_publ_contact_author_name     'Jasinski, Jerry P.'
_publ_contact_author_address
;
 Department of Chemistry
 Keene State College
 229 Main Street
 Keene, NH 03435-2001 USA
;
_publ_contact_author_email     jjasinski@keene.edu
_publ_contact_author_fax     '603 358 2897'
_publ_contact_author_phone     '603 358 2563'
_publ_section_title
;
2,3-Diiodo-1-(phenylsulfonyl)-1H-indole
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Rinderspacher, Alison'
;
?
;
;
  Department of Chemistry
  Dartmouth College
  Hanover, NH 03755-3564
  USA
;
    'Gribble, Gordon W.'
;
?
;
;
  Department of Chemistry
  Dartmouth College
  Hanover, NH 03755-3564
  USA
;
    'Butcher, Ray J.'
;
?
;
;
  Department of Chemistry
  Howard University
  Washington, DC 20059
  USA
;
    'Jasinski, Jerry P.'
;
?
;
;
  Department of Chemistry
  Keene State College
  Keene, NH 03435-2001
  USA
;
data_I
_chemical_name_systematic
;
2,3-Diiodo-1-(phenylsulfonyl)-1H-indole
;
_chemical_formula_moiety     'C14 H9 I2 N1 O2 S1'
_chemical_formula_sum     'C14 H9 I2 N1 O2 S1'
_chemical_formula_iupac     'C14 H9 I2 N1 O2 S1'
_chemical_formula_weight     509.11
_symmetry_cell_setting     'Monoclinic'
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '?'
loop_
    _symmetry_equiv_pos_as_xyz
    'x,y,z'
    '-x,-y,-z'
    '-x+1/2,y+1/2,-z+1/2'
    'x+1/2,-y+1/2,z+1/2'
_cell_length_a     10.4680(15)
_cell_length_b     11.9852(18)
_cell_length_c     12.4945(19)
_cell_angle_alpha     90
_cell_angle_beta     109.550(3)
_cell_angle_gamma     90
_cell_volume     1477.2(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3872
_cell_measurement_theta_min     2
_cell_measurement_theta_max     28
_cell_measurement_temperature     100
_exptl_crystal_description     'prism'
_exptl_crystal_colour     'violet'
_exptl_crystal_size_max     0.50
_exptl_crystal_size_mid     0.26
_exptl_crystal_size_min     0.12
_exptl_crystal_density_diffrn     2.289
_exptl_crystal_density_meas     ?
_exptl_crystal_F_000     952
_exptl_absorpt_coefficient_mu     4.398
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min     0.250
_exptl_absorpt_correction_T_max     0.5899
_exptl_special_details
;¹H NMR (CDCl₃): δ 8.29 (d, 1H, J = 7.2
Hz), 7.91 (d, 2H, J = 7.2 Hz), 7.59--7.52 (m, 2H), 7.45
(t, 2H,J = 8.1 Hz), 7.38--7.29 (m, 2H).
;
_diffrn_ambient_temperature     100
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device_type     'Bruker-Nonius Kappa Apex2'
_diffrn_measurement_method     'φ and ω'
_diffrn_reflns_number     9300
_diffrn_reflns_av_R_equivalents     0.044
_diffrn_reflns_theta_min     2.206
_diffrn_reflns_theta_max     28.416
_diffrn_reflns_theta_full     25.006
_diffrn_measured_fraction_theta_max     0.919
_diffrn_measured_fraction_theta_full     0.965
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     7
_diffrn_reflns_limit_k_min     -15
_diffrn_reflns_limit_k_max     15
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_limit_l_max     15
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_reflns_number_total     3407
_reflns_number_gt     2422
_reflns_threshold_expression     I>3.0σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0509
_refine_ls_R_factor_gt     0.0325
_refine_ls_wR_factor_all     0.0820
_refine_ls_wR_factor_gt     0.0815
_refine_ls_wR_factor_ref     0.0815
_refine_ls_goodness_of_fit_ref     0.9451
_refine_ls_number_reflns     2422
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     refall
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince,
1982)
[weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)]
where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(\dF/6\sF)²]²
Ai are:
37.8 38.0 29.3
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_refine_ls_shift/su_max     0.000294
_refine_diff_density_max     0.72
_refine_diff_density_min     -1.53
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_extinction_coef     6.2(16)
loop_
    _atom_type_symbol
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    C 0.0033 0.0016 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
    H 0.0000 0.0000 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
    N 0.0061 0.0033 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
    O 0.0106 0.0060 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
    S 0.1246 0.1234 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
    I -0.4742 1.8119 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'APEX2 (Bruker, 2006)'
_computing_cell_refinement     'SAINT-NT (Bruker, 2006)'
_computing_data_reduction     'SAINT-NT'
_computing_structure_solution     'SIR92 (Altomare et al.,  1994)'
_computing_structure_refinement     'CRYSTALS (Betteridge et al.,  2003)'
_computing_molecular_graphics     'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material     'CRYSTALS'
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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    I I1 0.49622(4) -0.39233(3) -0.16730(3) 0.0291 Uani 1.0000 . .
    I I2 0.47619(4) -0.26347(3) 0.10451(3) 0.0223 Uani 1.0000 . .
    S S1 0.68870(13) -0.17522(11) -0.25869(12) 0.0201 Uani 1.0000 . .
    O O1 0.6491(5) -0.2816(4) -0.3115(4) 0.0285 Uani 1.0000 . .
    O O2 0.8175(4) -0.1295(4) -0.2492(4) 0.0262 Uani 1.0000 . .
    N N1 0.6893(5) -0.1874(4) -0.1240(4) 0.0186 Uani 1.0000 . .
    C C2 0.5936(5) -0.2494(4) -0.0905(5) 0.0189 Uani 1.0000 . .
    C C3 0.5822(5) -0.2014(4) 0.0056(4) 0.0172 Uani 1.0000 . .
    C C4 0.6636(5) -0.1028(5) 0.0312(5) 0.0185 Uani 1.0000 . .
    C C5 0.6816(6) -0.0219(5) 0.1145(5) 0.0228 Uani 1.0000 . .
    C C6 0.7682(6) 0.0667(5) 0.1172(5) 0.0270 Uani 1.0000 . .
    C C7 0.8357(6) 0.0727(5) 0.0384(5) 0.0288 Uani 1.0000 . .
    C C8 0.8177(6) -0.0058(5) -0.0466(5) 0.0240 Uani 1.0000 . .
    C C9 0.7305(5) -0.0942(4) -0.0492(4) 0.0177 Uani 1.0000 . .
    C C10 0.5618(6) -0.0773(5) -0.3211(4) 0.0228 Uani 1.0000 . .
    C C11 0.4266(6) -0.1115(6) -0.3559(5) 0.0274 Uani 1.0000 . .
    C C12 0.3269(7) -0.0321(6) -0.4029(5) 0.0339 Uani 1.0000 . .
    C C13 0.3621(7) 0.0771(6) -0.4131(5) 0.0381 Uani 1.0000 . .
    C C14 0.4958(7) 0.1095(6) -0.3790(5) 0.0323 Uani 1.0000 . .
    C C15 0.5975(6) 0.0328(5) -0.3304(5) 0.0257 Uani 1.0000 . .
    H H51 0.6340 -0.0277 0.1716 0.0245 Uiso 1.0000 . .
    H H61 0.7820 0.1265 0.1758 0.0279 Uiso 1.0000 . .
    H H71 0.8993 0.1363 0.0433 0.0297 Uiso 1.0000 . .
    H H81 0.8654 0.0000 -0.1036 0.0255 Uiso 1.0000 . .
    H H111 0.4025 -0.1911 -0.3483 0.0331 Uiso 1.0000 . .
    H H121 0.2292 -0.0544 -0.4282 0.0395 Uiso 1.0000 . .
    H H131 0.2893 0.1336 -0.4466 0.0417 Uiso 1.0000 . .
    H H141 0.5195 0.1889 -0.3885 0.0376 Uiso 1.0000 . .
    H H151 0.6949 0.0560 -0.3034 0.0306 Uiso 1.0000 . .
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    I1 C2 . . 2.059(5) no
    I2 C3 . . 2.057(5) no
    S1 O1 . . 1.432(4) no
    S1 O2 . . 1.423(4) no
    S1 N1 . . 1.688(5) no
    S1 C10 . . 1.748(6) no
    N1 C2 . . 1.418(7) no
    N1 C9 . . 1.427(7) no
    C2 C3 . . 1.371(7) no
    C3 C4 . . 1.429(7) no
    C4 C5 . . 1.389(8) no
    C4 C9 . . 1.407(7) no
    C5 C6 . . 1.390(9) no
    C5 H51 . . 1.000 no
    C6 C7 . . 1.393(9) no
    C6 H61 . . 1.000 no
    C7 C8 . . 1.384(8) no
    C7 H71 . . 1.000 no
    C8 C9 . . 1.392(8) no
    C8 H81 . . 1.000 no
    C10 C11 . . 1.396(8) no
    C10 C15 . . 1.387(9) no
    C11 C12 . . 1.389(9) no
    C11 H111 . . 1.000 no
    C12 C13 . . 1.378(11) no
    C12 H121 . . 1.000 no
    C13 C14 . . 1.376(10) no
    C13 H131 . . 1.000 no
    C14 C15 . . 1.384(9) no
    C14 H141 . . 1.000 no
    C15 H151 . . 1.000 no
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_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O1 S1 O2 . . . 120.1(3) no
    O1 S1 N1 . . . 106.6(2) no
    O2 S1 N1 . . . 105.3(2) no
    O1 S1 C10 . . . 109.4(3) no
    O2 S1 C10 . . . 109.6(3) no
    N1 S1 C10 . . . 104.6(2) no
    S1 N1 C2 . . . 124.9(4) no
    S1 N1 C9 . . . 119.0(4) no
    C2 N1 C9 . . . 107.8(4) no
    N1 C2 I1 . . . 125.9(4) no
    N1 C2 C3 . . . 108.4(4) no
    I1 C2 C3 . . . 125.6(4) no
    C2 C3 I2 . . . 126.6(4) no
    C2 C3 C4 . . . 108.8(5) no
    I2 C3 C4 . . . 124.4(4) no
    C3 C4 C5 . . . 131.8(5) no
    C3 C4 C9 . . . 107.6(5) no
    C5 C4 C9 . . . 120.6(5) no
    C4 C5 C6 . . . 118.4(5) no
    C4 C5 H51 . . . 120.8 no
    C6 C5 H51 . . . 120.8 no
    C5 C6 C7 . . . 120.2(5) no
    C5 C6 H61 . . . 119.9 no
    C7 C6 H61 . . . 119.9 no
    C6 C7 C8 . . . 122.4(6) no
    C6 C7 H71 . . . 118.7 no
    C8 C7 H71 . . . 118.9 no
    C7 C8 C9 . . . 117.1(5) no
    C7 C8 H81 . . . 121.8 no
    C9 C8 H81 . . . 121.0 no
    N1 C9 C4 . . . 107.2(4) no
    N1 C9 C8 . . . 131.6(5) no
    C4 C9 C8 . . . 121.2(5) no
    S1 C10 C11 . . . 118.8(5) no
    S1 C10 C15 . . . 119.4(4) no
    C11 C10 C15 . . . 121.8(5) no
    C10 C11 C12 . . . 118.1(6) no
    C10 C11 H111 . . . 120.8 no
    C12 C11 H111 . . . 121.1 no
    C11 C12 C13 . . . 120.2(6) no
    C11 C12 H121 . . . 119.7 no
    C13 C12 H121 . . . 120.1 no
    C12 C13 C14 . . . 121.0(6) no
    C12 C13 H131 . . . 119.5 no
    C14 C13 H131 . . . 119.5 no
    C13 C14 C15 . . . 120.2(7) no
    C13 C14 H141 . . . 119.9 no
    C15 C14 H141 . . . 119.9 no
    C10 C15 C14 . . . 118.7(6) no
    C10 C15 H151 . . . 120.6 no
    C14 C15 H151 . . . 120.8 no
