#------------------------------------------------------------------------------
#$Date: 2009-11-16 01:43:51 +0000 (Mon, 16 Nov 2009) $
#$Revision: 853 $
#$URL: svn://www.crystallography.net/cod/cif/2/2203480.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_2203480
_space_group_IT_number           15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_[local]_cod_cif_authors_sg_H-M  'C 2/c'
loop_
_publ_author_name
'Huang, Xiang-Hong'
'Zhang, Qian-Feng'
'Sung, Herman H. Y.'
_publ_section_title
;
4-Bromo-N-(2-phenyl-1H-indol-7-yl)benzenesulfonamide
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica, Section E'
_journal_page_first              o488
_journal_page_last               o489
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C20 H15 Br N2 O2 S'
_chemical_formula_moiety         'C20 H15 Br N2 O2 S'
_chemical_formula_sum            'C20 H15 Br N2 O2 S'
_chemical_formula_weight         427.31
_chemical_name_systematic
;
4-Bromo-N-(2-phenyl-1H-indol-7-yl)benzenesulfonamide
;
_symmetry_cell_setting           Monoclinic
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 114.332(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   30.764(14)
_cell_length_b                   4.922(2)
_cell_length_c                   26.335(13)
_cell_measurement_reflns_used    2144
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      21.72
_cell_measurement_theta_min      2.65
_cell_volume                     3633(3)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1999)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997b)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       '\f and \w'
_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  0.0504
_diffrn_reflns_av_sigmaI/netI    0.0482
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            15353
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.70
_exptl_absorpt_coefficient_mu    2.395
_exptl_absorpt_correction_T_max  0.698
_exptl_absorpt_correction_T_min  0.607
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1997a)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       bar
_exptl_crystal_F_000             1728
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.748
_refine_diff_density_min         -0.479
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.964
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3524
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.964
_refine_ls_R_factor_all          0.0916
_refine_ls_R_factor_gt           0.0427
_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/[\s^2^(Fo^2^)+(0.0552P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.1075
_reflns_number_gt                2106
_reflns_number_total             3524
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    ob6351.cif
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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_
_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_type_symbol
Br1 0.035975(15) -0.16015(11) 0.185976(17) 0.0892(2) Uani d . 1 Br
S1 0.20783(3) 0.18035(16) 0.41436(3) 0.0392(2) Uani d . 1 S
O1 0.19605(7) 0.0927(5) 0.45857(9) 0.0522(6) Uani d . 1 O
O2 0.21876(8) 0.4562(4) 0.40998(9) 0.0513(6) Uani d . 1 O
N1 0.25367(8) 0.0034(5) 0.41938(9) 0.0370(6) Uani d . 1 N
H1 0.2466 -0.1745 0.4182 0.044 Uiso d R 1 H
N2 0.33162(8) 0.4082(5) 0.44433(10) 0.0376(6) Uani d . 1 N
H2B 0.3196 0.4275 0.4700 0.045 Uiso d R 1 H
C1 0.08611(11) -0.0514(8) 0.25395(13) 0.0545(9) Uani d . 1 C
C2 0.09056(12) -0.1726(8) 0.30264(15) 0.0600(10) Uani d . 1 C
H2A 0.0686 -0.3029 0.3025 0.072 Uiso calc R 1 H
C3 0.12774(11) -0.1001(7) 0.35179(14) 0.0519(9) Uani d . 1 C
H3A 0.1312 -0.1814 0.3851 0.062 Uiso calc R 1 H
C4 0.15975(10) 0.0937(6) 0.35122(12) 0.0388(7) Uani d . 1 C
C5 0.15456(12) 0.2150(8) 0.30206(14) 0.0538(9) Uani d . 1 C
H5A 0.1761 0.3474 0.3021 0.065 Uiso calc R 1 H
C6 0.11761(13) 0.1418(8) 0.25276(15) 0.0608(10) Uani d . 1 C
H6A 0.1141 0.2220 0.2193 0.073 Uiso calc R 1 H
C7 0.31332(10) 0.2441(6) 0.39825(12) 0.0351(7) Uani d . 1 C
C8 0.27683(10) 0.0553(6) 0.38262(12) 0.0376(7) Uani d . 1 C
C9 0.26606(12) -0.0899(6) 0.33427(13) 0.0462(8) Uani d . 1 C
H8A 0.2418 -0.2185 0.3232 0.055 Uiso calc R 1 H
C10 0.29172(12) -0.0441(7) 0.30159(13) 0.0525(9) Uani d . 1 C
H9A 0.2836 -0.1399 0.2685 0.063 Uiso calc R 1 H
C11 0.32828(13) 0.1385(7) 0.31756(14) 0.0518(9) Uani d . 1 C
H10A 0.3451 0.1658 0.2956 0.062 Uiso calc R 1 H
C12 0.34029(11) 0.2835(7) 0.36681(13) 0.0430(8) Uani d . 1 C
C13 0.37682(11) 0.4699(7) 0.39809(13) 0.0478(8) Uani d . 1 C
H12A 0.4006 0.5339 0.3880 0.057 Uiso calc R 1 H
C14 0.37140(10) 0.5387(6) 0.44461(13) 0.0409(7) Uani d . 1 C
C15 0.39993(11) 0.7197(6) 0.49081(13) 0.0419(8) Uani d . 1 C
C16 0.44886(12) 0.7380(8) 0.50572(15) 0.0579(10) Uani d . 1 C
H16A 0.4625 0.6369 0.4863 0.070 Uiso calc R 1 H
C17 0.47709(13) 0.9019(9) 0.54840(16) 0.0696(12) Uani d . 1 C
H17A 0.5098 0.9094 0.5582 0.084 Uiso calc R 1 H
C18 0.45725(14) 1.0559(9) 0.57699(15) 0.0657(11) Uani d . 1 C
H18A 0.4763 1.1691 0.6059 0.079 Uiso calc R 1 H
C19 0.40928(13) 1.0413(7) 0.56263(14) 0.0559(9) Uani d . 1 C
H19A 0.3957 1.1460 0.5817 0.067 Uiso calc R 1 H
C20 0.38083(12) 0.8720(6) 0.52002(13) 0.0454(8) Uani d . 1 C
H20A 0.3483 0.8615 0.5111 0.054 Uiso calc R 1 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Br1 0.0617(3) 0.1247(5) 0.0558(3) -0.0146(3) -0.0012(2) -0.0095(3)
S1 0.0418(5) 0.0371(5) 0.0399(4) -0.0078(4) 0.0179(3) -0.0069(4)
O1 0.0513(14) 0.0681(16) 0.0441(13) -0.0123(12) 0.0267(11) -0.0105(11)
O2 0.0534(14) 0.0305(13) 0.0645(14) -0.0062(11) 0.0187(11) -0.0073(11)
N1 0.0425(14) 0.0278(14) 0.0421(14) -0.0070(12) 0.0187(12) -0.0007(11)
N2 0.0364(14) 0.0399(15) 0.0398(14) -0.0036(12) 0.0191(11) 0.0005(12)
C1 0.0403(19) 0.071(2) 0.0395(19) -0.0013(18) 0.0038(15) -0.0060(17)
C2 0.046(2) 0.073(3) 0.056(2) -0.0207(19) 0.0151(17) -0.006(2)
C3 0.048(2) 0.059(2) 0.0462(19) -0.0133(18) 0.0169(16) 0.0021(16)
C4 0.0372(17) 0.0403(19) 0.0400(17) -0.0007(15) 0.0170(14) -0.0011(14)
C5 0.058(2) 0.055(2) 0.051(2) -0.0159(18) 0.0243(18) 0.0020(17)
C6 0.063(2) 0.070(3) 0.045(2) -0.002(2) 0.0174(18) 0.0083(19)
C7 0.0387(17) 0.0321(18) 0.0345(16) 0.0016(13) 0.0151(14) 0.0034(13)
C8 0.0395(17) 0.0345(17) 0.0381(16) -0.0007(15) 0.0153(14) 0.0014(14)
C9 0.050(2) 0.0386(19) 0.0473(19) -0.0050(16) 0.0174(16) -0.0042(15)
C10 0.064(2) 0.052(2) 0.0416(18) 0.001(2) 0.0218(17) -0.0117(17)
C11 0.063(2) 0.054(2) 0.0468(19) -0.0033(19) 0.0318(18) -0.0033(17)
C12 0.0444(19) 0.044(2) 0.0471(19) 0.0005(15) 0.0257(16) 0.0016(15)
C13 0.0420(19) 0.055(2) 0.051(2) -0.0078(17) 0.0247(16) 0.0019(17)
C14 0.0376(18) 0.0395(19) 0.0465(18) 0.0002(15) 0.0183(15) 0.0063(15)
C15 0.0410(18) 0.0381(18) 0.0412(17) -0.0077(15) 0.0114(15) 0.0031(15)
C16 0.040(2) 0.073(3) 0.060(2) -0.0079(18) 0.0202(18) -0.0044(19)
C17 0.042(2) 0.093(3) 0.063(2) -0.025(2) 0.0108(19) 0.005(2)
C18 0.065(3) 0.064(3) 0.050(2) -0.019(2) 0.006(2) 0.0002(19)
C19 0.060(2) 0.046(2) 0.056(2) -0.0035(19) 0.0181(18) -0.0053(18)
C20 0.0420(18) 0.041(2) 0.0480(18) -0.0016(15) 0.0130(15) 0.0042(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C1 1.896(3) yes
S1 O2 1.415(2) yes
S1 O1 1.421(2) yes
S1 N1 1.616(3) yes
S1 C4 1.763(3) yes
N1 C8 1.442(4) yes
N1 H1 0.9000 ?
N2 C7 1.371(4) yes
N2 C14 1.380(4) yes
N2 H2B 0.8998 ?
C1 C6 1.367(5) ?
C1 C2 1.369(5) ?
C2 C3 1.375(5) ?
C2 H2A 0.9300 ?
C3 C4 1.375(4) ?
C3 H3A 0.9300 ?
C4 C5 1.374(4) ?
C5 C6 1.375(5) ?
C5 H5A 0.9300 ?
C6 H6A 0.9300 ?
C7 C8 1.383(4) ?
C7 C12 1.406(4) ?
C8 C9 1.376(4) ?
C9 C10 1.405(5) ?
C9 H8A 0.9300 ?
C10 C11 1.364(5) ?
C10 H9A 0.9300 ?
C11 C12 1.390(4) ?
C11 H10A 0.9300 ?
C12 C13 1.421(4) ?
C13 C14 1.346(4) ?
C13 H12A 0.9300 ?
C14 C15 1.471(4) ?
C15 C20 1.368(4) ?
C15 C16 1.393(4) ?
C16 C17 1.365(5) ?
C16 H16A 0.9300 ?
C17 C18 1.376(6) ?
C17 H17A 0.9300 ?
C18 C19 1.366(5) ?
C18 H18A 0.9300 ?
C19 C20 1.382(4) ?
C19 H19A 0.9300 ?
C20 H20A 0.9300 ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
O2 S1 O1 120.50(14) yes
O2 S1 N1 107.16(13) yes
O1 S1 N1 106.13(13) yes
O2 S1 C4 106.88(14) yes
O1 S1 C4 107.54(14) yes
N1 S1 C4 108.15(13) yes
C8 N1 S1 120.39(19) yes
C8 N1 H1 109.2 ?
S1 N1 H1 109.3 ?
C7 N2 C14 108.6(2) yes
C7 N2 H2B 125.6 ?
C14 N2 H2B 125.8 ?
C6 C1 C2 121.8(3) ?
C6 C1 Br1 118.9(3) no
C2 C1 Br1 119.3(3) no
C1 C2 C3 119.5(3) ?
C1 C2 H2A 120.3 ?
C3 C2 H2A 120.3 ?
C2 C3 C4 119.4(3) ?
C2 C3 H3A 120.3 ?
C4 C3 H3A 120.3 ?
C5 C4 C3 120.4(3) ?
C5 C4 S1 120.7(2) no
C3 C4 S1 118.9(2) no
C4 C5 C6 120.4(3) ?
C4 C5 H5A 119.8 ?
C6 C5 H5A 119.8 ?
C1 C6 C5 118.6(3) ?
C1 C6 H6A 120.7 ?
C5 C6 H6A 120.7 ?
N2 C7 C8 130.3(3) no
N2 C7 C12 108.3(3) no
C8 C7 C12 121.4(3) ?
C9 C8 C7 118.7(3) ?
C9 C8 N1 122.2(3) no
C7 C8 N1 119.0(3) no
C8 C9 C10 120.1(3) ?
C8 C9 H8A 120.0 ?
C10 C9 H8A 120.0 ?
C11 C10 C9 121.1(3) ?
C11 C10 H9A 119.4 ?
C9 C10 H9A 119.4 ?
C10 C11 C12 119.6(3) ?
C10 C11 H10A 120.2 ?
C12 C11 H10A 120.2 ?
C11 C12 C7 118.9(3) ?
C11 C12 C13 135.6(3) ?
C7 C12 C13 105.4(3) ?
C14 C13 C12 109.0(3) ?
C14 C13 H12A 125.5 ?
C12 C13 H12A 125.5 ?
C13 C14 N2 108.7(3) ?
C13 C14 C15 130.5(3) ?
N2 C14 C15 120.8(3) no
C20 C15 C16 118.1(3) ?
C20 C15 C14 123.3(3) ?
C16 C15 C14 118.6(3) ?
C17 C16 C15 121.1(4) ?
C17 C16 H16A 119.4 ?
C15 C16 H16A 119.4 ?
C16 C17 C18 120.1(4) ?
C16 C17 H17A 120.0 ?
C18 C17 H17A 120.0 ?
C19 C18 C17 119.5(4) ?
C19 C18 H18A 120.3 ?
C17 C18 H18A 120.3 ?
C18 C19 C20 120.5(4) ?
C18 C19 H19A 119.8 ?
C20 C19 H19A 119.8 ?
C15 C20 C19 120.8(3) ?
C15 C20 H20A 119.6 ?
C19 C20 H20A 119.6 ?
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
N1 H1 O2 1_545 0.90 1.98 2.872(3) 170 yes
N2 H2B O1 7_556 0.90 2.13 3.009(4) 167 yes