#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/76/2227689.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2227689
loop_
_publ_author_name
'Chakkaravarthi, G.'
'Panchatcharam, R.'
'Dhayalan, V.'
'Mohanakrishnan, A. K.'
'Manivannan, V.'
_publ_section_title
;
 (4-Bromophenyl)(1-phenylsulfonyl-1H-indol-2-yl)methanone
;
_journal_coeditor_code           IS2617
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2957
_journal_paper_doi               10.1107/S160053681004198X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C21 H14 Br N O3 S'
_chemical_formula_moiety         'C21 H14 Br N O3 S'
_chemical_formula_sum            'C21 H14 Br N O3 S'
_chemical_formula_weight         440.30
_chemical_name_systematic
;
(4-Bromophenyl)(1-phenylsulfonyl-1H-indol-2-yl)methanone
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 93.388(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.482(3)
_cell_length_b                   25.780(4)
_cell_length_c                   8.690(3)
_cell_measurement_reflns_used    4249
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      24.4
_cell_measurement_theta_min      2.5
_cell_volume                     1896.9(10)
_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 0.990
_diffrn_measured_fraction_theta_max 0.990
_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  0.0351
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            18123
_diffrn_reflns_theta_full        28.41
_diffrn_reflns_theta_max         28.41
_diffrn_reflns_theta_min         1.58
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.298
_exptl_absorpt_correction_T_max  0.6564
_exptl_absorpt_correction_T_min  0.6085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.615
_refine_diff_density_min         -0.460
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         4736
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0841
_refine_ls_R_factor_gt           0.0440
_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)+(0.0445P)²+0.6759P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0974
_refine_ls_wR_factor_ref         0.1111
_reflns_number_gt                2944
_reflns_number_total             4736
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            is2617.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2227689
_cod_database_fobs_code          2227689
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'
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 . .
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'
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_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_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
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_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656266
