##############################################################################
###                                                                        ###
###        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/  #
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# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
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data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(4-Bromophenyl)(1-phenylsulfonyl-1H-indol-2-yl)methanone
;
_chemical_name_common     ?
_chemical_formula_moiety     'C21 H14 Br N O3 S'
_chemical_formula_sum     'C21 H14 Br N O3 S'
_chemical_formula_iupac     'C21 H14 Br N O3 S'
_chemical_formula_weight     440.30
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     8.482(3)
_cell_length_b     25.780(4)
_cell_length_c     8.690(3)
_cell_angle_alpha     90.00
_cell_angle_beta     93.388(3)
_cell_angle_gamma     90.00
_cell_volume     1896.9(10)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     4249
_cell_measurement_theta_min     2.5
_cell_measurement_theta_max     24.4
_cell_measurement_temperature     295(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.24
_exptl_crystal_size_mid     0.22
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.542
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     888
_exptl_absorpt_coefficient_mu     2.298
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.6085
_exptl_absorpt_correction_T_max     0.6564
_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     18123
_diffrn_reflns_av_R_equivalents     0.0351
_diffrn_reflns_av_sigmaI/netI     0.0373
_diffrn_reflns_theta_min     1.58
_diffrn_reflns_theta_max     28.41
_diffrn_reflns_theta_full     28.41
_diffrn_measured_fraction_theta_max     0.990
_diffrn_measured_fraction_theta_full     0.990
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -29
_diffrn_reflns_limit_k_max     34
_diffrn_reflns_limit_l_min     -9
_diffrn_reflns_limit_l_max     11
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     ?
_refine_special_details
;
;
_reflns_number_total     4736
_reflns_number_gt     2944
_reflns_threshold_expression     I>2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0841
_refine_ls_R_factor_gt     0.0440
_refine_ls_wR_factor_gt     0.0974
_refine_ls_wR_factor_ref     0.1111
_refine_ls_goodness_of_fit_ref     1.033
_refine_ls_restrained_S_all     1.033
_refine_ls_number_reflns     4736
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0445P)²+0.6759P] 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     0.615
_refine_diff_density_min     -0.460
_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'
    'Br' 'Br' -0.2901 2.4595
                         '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
    Br Br1 0.24312(5) 0.018422(12) 0.53534(5) 0.09126(18) Uani d . 1 . .
    S S1 0.26404(8) 0.34303(3) 0.83609(7) 0.04855(18) Uani d . 1 . .
    O O1 0.3198(2) 0.38893(8) 0.9118(2) 0.0648(5) Uani d . 1 . .
    O O2 0.2576(3) 0.29550(8) 0.9169(2) 0.0737(6) Uani d . 1 . .
    O O3 0.5440(2) 0.24395(7) 0.8349(2) 0.0671(6) Uani d . 1 . .
    N N1 0.3837(2) 0.33357(7) 0.6910(2) 0.0421(5) Uani d . 1 . .
    C C1 0.0793(3) 0.35548(11) 0.7418(3) 0.0494(6) Uani d . 1 . .
    C C2 0.0204(4) 0.40492(12) 0.7428(4) 0.0703(9) Uani d . 1 . .
    H H2 0.0751 0.4312 0.7965 0.084 Uiso calc R 1 . .
    C C3 -0.1230(4) 0.41519(17) 0.6619(5) 0.0963(12) Uani d . 1 . .
    H H3 -0.1637 0.4487 0.6586 0.116 Uiso calc R 1 . .
    C C4 -0.2035(4) 0.3756(2) 0.5872(5) 0.1035(14) Uani d . 1 . .
    H H4 -0.3000 0.3824 0.5347 0.124 Uiso calc R 1 . .
    C C5 -0.1456(4) 0.32696(18) 0.5883(4) 0.0901(12) Uani d . 1 . .
    H H5 -0.2021 0.3006 0.5369 0.108 Uiso calc R 1 . .
    C C6 -0.0021(4) 0.31602(12) 0.6658(3) 0.0650(8) Uani d . 1 . .
    H H6 0.0386 0.2825 0.6665 0.078 Uiso calc R 1 . .
    C C7 0.4047(3) 0.28357(9) 0.6256(3) 0.0410(5) Uani d . 1 . .
    C C8 0.4166(3) 0.28833(10) 0.4728(3) 0.0488(6) Uani d . 1 . .
    H H8 0.4315 0.2612 0.4045 0.059 Uiso calc R 1 . .
    C C9 0.4027(3) 0.34192(10) 0.4327(3) 0.0477(6) Uani d . 1 . .
    C C10 0.4108(4) 0.36829(14) 0.2933(4) 0.0706(9) Uani d . 1 . .
    H H10 0.4263 0.3505 0.2024 0.085 Uiso calc R 1 . .
    C C11 0.3955(4) 0.42089(15) 0.2939(4) 0.0827(11) Uani d . 1 . .
    H H11 0.4003 0.4391 0.2019 0.099 Uiso calc R 1 . .
    C C12 0.3731(4) 0.44741(12) 0.4272(5) 0.0769(10) Uani d . 1 . .
    H H12 0.3629 0.4833 0.4230 0.092 Uiso calc R 1 . .
    C C13 0.3650(3) 0.42278(11) 0.5686(4) 0.0613(7) Uani d . 1 . .
    H H13 0.3494 0.4410 0.6587 0.074 Uiso calc R 1 . .
    C C14 0.3816(3) 0.36928(9) 0.5669(3) 0.0438(6) Uani d . 1 . .
    C C15 0.4561(3) 0.23788(10) 0.7209(3) 0.0471(6) Uani d . 1 . .
    C C16 0.4037(3) 0.18560(9) 0.6675(3) 0.0430(6) Uani d . 1 . .
    C C17 0.2741(3) 0.17786(10) 0.5660(3) 0.0486(6) Uani d . 1 . .
    H H17 0.2187 0.2062 0.5244 0.058 Uiso calc R 1 . .
    C C18 0.2266(3) 0.12794(11) 0.5260(3) 0.0566(7) Uani d . 1 . .
    H H18 0.1389 0.1226 0.4584 0.068 Uiso calc R 1 . .
    C C19 0.3100(3) 0.08671(10) 0.5870(3) 0.0566(7) Uani d . 1 . .
    C C20 0.4411(4) 0.09344(11) 0.6858(4) 0.0656(8) Uani d . 1 . .
    H H20 0.4980 0.0650 0.7246 0.079 Uiso calc R 1 . .
    C C21 0.4865(3) 0.14285(10) 0.7260(3) 0.0586(7) Uani d . 1 . .
    H H21 0.5744 0.1478 0.7936 0.070 Uiso calc R 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
    Br1 C19 . 1.895(3) ?
    S1 O2 . 1.415(2) ?
    S1 O1 . 1.4211(19) ?
    S1 N1 . 1.682(2) ?
    S1 C1 . 1.754(3) ?
    O3 C15 . 1.215(3) ?
    N1 C14 . 1.417(3) ?
    N1 C7 . 1.424(3) ?
    C1 C2 . 1.369(4) ?
    C1 C6 . 1.376(4) ?
    C2 C3 . 1.394(5) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.370(5) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.346(6) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.385(5) ?
    C5 H5 . 0.9300 ?
    C6 H6 . 0.9300 ?
    C7 C8 . 1.343(3) ?
    C7 C15 . 1.490(3) ?
    C8 C9 . 1.428(4) ?
    C8 H8 . 0.9300 ?
    C9 C14 . 1.384(4) ?
    C9 C10 . 1.394(4) ?
    C10 C11 . 1.362(5) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.368(5) ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.388(4) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.386(3) ?
    C13 H13 . 0.9300 ?
    C15 C16 . 1.485(3) ?
    C16 C17 . 1.382(3) ?
    C16 C21 . 1.387(3) ?
    C17 C18 . 1.387(4) ?
    C17 H17 . 0.9300 ?
    C18 C19 . 1.367(4) ?
    C18 H18 . 0.9300 ?
    C19 C20 . 1.375(4) ?
    C20 C21 . 1.370(4) ?
    C20 H20 . 0.9300 ?
    C21 H21 . 0.9300 ?
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
    O2 S1 O1 . . 120.86(13) ?
    O2 S1 N1 . . 106.80(11) ?
    O1 S1 N1 . . 105.58(12) ?
    O2 S1 C1 . . 109.31(14) ?
    O1 S1 C1 . . 109.10(12) ?
    N1 S1 C1 . . 103.79(11) ?
    C14 N1 C7 . . 106.31(19) ?
    C14 N1 S1 . . 119.67(16) ?
    C7 N1 S1 . . 121.71(16) ?
    C2 C1 C6 . . 121.2(3) ?
    C2 C1 S1 . . 118.9(2) ?
    C6 C1 S1 . . 119.9(2) ?
    C1 C2 C3 . . 118.8(3) ?
    C1 C2 H2 . . 120.6 ?
    C3 C2 H2 . . 120.6 ?
    C4 C3 C2 . . 119.6(4) ?
    C4 C3 H3 . . 120.2 ?
    C2 C3 H3 . . 120.2 ?
    C5 C4 C3 . . 121.3(4) ?
    C5 C4 H4 . . 119.4 ?
    C3 C4 H4 . . 119.4 ?
    C4 C5 C6 . . 120.2(3) ?
    C4 C5 H5 . . 119.9 ?
    C6 C5 H5 . . 119.9 ?
    C1 C6 C5 . . 119.0(3) ?
    C1 C6 H6 . . 120.5 ?
    C5 C6 H6 . . 120.5 ?
    C8 C7 N1 . . 109.3(2) ?
    C8 C7 C15 . . 125.8(2) ?
    N1 C7 C15 . . 122.2(2) ?
    C7 C8 C9 . . 108.6(2) ?
    C7 C8 H8 . . 125.7 ?
    C9 C8 H8 . . 125.7 ?
    C14 C9 C10 . . 120.0(3) ?
    C14 C9 C8 . . 107.5(2) ?
    C10 C9 C8 . . 132.5(3) ?
    C11 C10 C9 . . 118.2(3) ?
    C11 C10 H10 . . 120.9 ?
    C9 C10 H10 . . 120.9 ?
    C10 C11 C12 . . 121.2(3) ?
    C10 C11 H11 . . 119.4 ?
    C12 C11 H11 . . 119.4 ?
    C11 C12 C13 . . 122.5(3) ?
    C11 C12 H12 . . 118.7 ?
    C13 C12 H12 . . 118.7 ?
    C14 C13 C12 . . 115.8(3) ?
    C14 C13 H13 . . 122.1 ?
    C12 C13 H13 . . 122.1 ?
    C9 C14 C13 . . 122.3(2) ?
    C9 C14 N1 . . 108.3(2) ?
    C13 C14 N1 . . 129.4(2) ?
    O3 C15 C16 . . 122.0(2) ?
    O3 C15 C7 . . 119.8(2) ?
    C16 C15 C7 . . 118.1(2) ?
    C17 C16 C21 . . 119.0(2) ?
    C17 C16 C15 . . 122.8(2) ?
    C21 C16 C15 . . 118.1(2) ?
    C16 C17 C18 . . 120.2(2) ?
    C16 C17 H17 . . 119.9 ?
    C18 C17 H17 . . 119.9 ?
    C19 C18 C17 . . 119.2(2) ?
    C19 C18 H18 . . 120.4 ?
    C17 C18 H18 . . 120.4 ?
    C18 C19 C20 . . 121.7(3) ?
    C18 C19 Br1 . . 119.3(2) ?
    C20 C19 Br1 . . 119.0(2) ?
    C21 C20 C19 . . 118.8(3) ?
    C21 C20 H20 . . 120.6 ?
    C19 C20 H20 . . 120.6 ?
    C20 C21 C16 . . 121.1(2) ?
    C20 C21 H21 . . 119.4 ?
    C16 C21 H21 . . 119.4 ?
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 S1 N1 C14 . . . . 163.63(18) ?
    O1 S1 N1 C14 . . . . -66.5(2) ?
    C1 S1 N1 C14 . . . . 48.2(2) ?
    O2 S1 N1 C7 . . . . 26.6(2) ?
    O1 S1 N1 C7 . . . . 156.43(18) ?
    C1 S1 N1 C7 . . . . -88.8(2) ?
    O2 S1 C1 C2 . . . . 138.5(2) ?
    O1 S1 C1 C2 . . . . 4.3(3) ?
    N1 S1 C1 C2 . . . . -107.9(2) ?
    O2 S1 C1 C6 . . . . -42.9(3) ?
    O1 S1 C1 C6 . . . . -177.1(2) ?
    N1 S1 C1 C6 . . . . 70.7(2) ?
    C6 C1 C2 C3 . . . . -1.5(5) ?
    S1 C1 C2 C3 . . . . 177.1(3) ?
    C1 C2 C3 C4 . . . . 1.8(6) ?
    C2 C3 C4 C5 . . . . -1.1(7) ?
    C3 C4 C5 C6 . . . . 0.0(6) ?
    C2 C1 C6 C5 . . . . 0.5(4) ?
    S1 C1 C6 C5 . . . . -178.1(2) ?
    C4 C5 C6 C1 . . . . 0.3(5) ?
    C14 N1 C7 C8 . . . . 0.7(3) ?
    S1 N1 C7 C8 . . . . 142.63(19) ?
    C14 N1 C7 C15 . . . . 163.0(2) ?
    S1 N1 C7 C15 . . . . -55.1(3) ?
    N1 C7 C8 C9 . . . . -0.4(3) ?
    C15 C7 C8 C9 . . . . -161.9(2) ?
    C7 C8 C9 C14 . . . . -0.1(3) ?
    C7 C8 C9 C10 . . . . 178.0(3) ?
    C14 C9 C10 C11 . . . . -0.8(4) ?
    C8 C9 C10 C11 . . . . -178.7(3) ?
    C9 C10 C11 C12 . . . . 0.2(5) ?
    C10 C11 C12 C13 . . . . 0.1(5) ?
    C11 C12 C13 C14 . . . . 0.2(5) ?
    C10 C9 C14 C13 . . . . 1.2(4) ?
    C8 C9 C14 C13 . . . . 179.6(2) ?
    C10 C9 C14 N1 . . . . -177.8(2) ?
    C8 C9 C14 N1 . . . . 0.6(3) ?
    C12 C13 C14 C9 . . . . -0.9(4) ?
    C12 C13 C14 N1 . . . . 177.9(3) ?
    C7 N1 C14 C9 . . . . -0.8(3) ?
    S1 N1 C14 C9 . . . . -143.64(18) ?
    C7 N1 C14 C13 . . . . -179.7(2) ?
    S1 N1 C14 C13 . . . . 37.5(3) ?
    C8 C7 C15 O3 . . . . 127.2(3) ?
    N1 C7 C15 O3 . . . . -32.1(4) ?
    C8 C7 C15 C16 . . . . -49.7(4) ?
    N1 C7 C15 C16 . . . . 151.0(2) ?
    O3 C15 C16 C17 . . . . 162.2(3) ?
    C7 C15 C16 C17 . . . . -20.9(4) ?
    O3 C15 C16 C21 . . . . -16.0(4) ?
    C7 C15 C16 C21 . . . . 160.8(2) ?
    C21 C16 C17 C18 . . . . 1.2(4) ?
    C15 C16 C17 C18 . . . . -177.0(2) ?
    C16 C17 C18 C19 . . . . -0.5(4) ?
    C17 C18 C19 C20 . . . . -0.8(5) ?
    C17 C18 C19 Br1 . . . . 178.9(2) ?
    C18 C19 C20 C21 . . . . 1.4(5) ?
    Br1 C19 C20 C21 . . . . -178.3(2) ?
    C19 C20 C21 C16 . . . . -0.7(5) ?
    C17 C16 C21 C20 . . . . -0.6(4) ?
    C15 C16 C21 C20 . . . . 177.7(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
    C17 H17 O3 4_565 0.93 2.50 3.383(3) 158 y
    C4 H4 Cg1 1_455 0.93 2.67 3.635(4) 127 y
    C4 H4 Cg2 1_455 0.93 2.76 3.681(4) 169 y
data_global
_journal_date_recd_electronic     2010-10-14
_journal_date_accepted     2010-10-16
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue     11
_journal_page_first     o2957
_journal_page_last     o2957
_journal_paper_category     QO
_journal_coeditor_code     IS2617
_publ_contact_author_name     'G.Chakkaravarthi'
_publ_contact_author_address
;
Department of Physics
CPCL Polytechnic College
Chennai 600 068
India
;
_publ_contact_author_email     chakkaravarthi_2005@yahoo.com
_publ_contact_author_fax     ?
_publ_contact_author_phone     '04425550241'
_publ_section_title
;
(4-Bromophenyl)(1-phenylsulfonyl-1H-indol-2-yl)methanone
;
loop_
    _publ_author_name
    _publ_author_address
    'G. Chakkaravarthi'
;
Department of Physics
CPCL Polytechnic College
Chennai 600 068
India
;
    'R. Panchatcharam'
;
Department of Research and Development
PRIST University
Vallam
Thanjavur 613 403
Tamil Nadu
India
;
    'V. Dhayalan'
;
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
;
    'V. Manivannan'
;
Department of Research and Development
PRIST University
Vallam
Thanjavur 613 403
Tamil Nadu
India
;
_publ_section_synopsis     .
