#------------------------------------------------------------------------------
#$Date$
#$Revision$
#$URL$
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#
# 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_2218184
loop_
_publ_author_name
'Rizal, Mohd. Razali'
'Ali, Hapipah Mohd.'
'Ng, Seik Weng'
_publ_section_title
;
 5-Bromo-1<i>H</i>-indole-3-carbaldehyde thiosemicarbazone
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o918
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C10 H9 Br N4 S'
_chemical_formula_moiety         'C10 H9 Br N4 S'
_chemical_formula_sum            'C10 H9 Br N4 S'
_chemical_formula_weight         297.18
_chemical_name_systematic
;
5-Bromo-1H-indole-3-carboxaldehyde thiosemicarbazone
;
_space_group_IT_number           2
_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                69.2800(10)
_cell_angle_beta                 79.9690(10)
_cell_angle_gamma                72.8860(10)
_cell_formula_units_Z            2
_cell_length_a                   6.7731(2)
_cell_length_b                   8.7551(2)
_cell_length_c                   10.6539(2)
_cell_measurement_reflns_used    6604
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.3
_cell_measurement_theta_min      4.0
_cell_volume                     563.00(2)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       \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  0.0246
_diffrn_reflns_av_sigmaI/netI    0.0296
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6176
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.05
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.812
_exptl_absorpt_correction_T_max  0.516
_exptl_absorpt_correction_T_min  0.381
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.753
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.396
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     161
_refine_ls_number_reflns         2563
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0242
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0383P)^2^+0.1P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0638
_refine_ls_wR_factor_ref         0.0656
_reflns_number_gt                2281
_reflns_number_total             2563
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    lh2609.cif
_[local]_cod_data_source_block   I
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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'
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_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
Br Br1 0.51693(4) 0.13022(2) 0.31237(2) 0.02102(9) Uani d . 1
S S1 0.01187(9) 0.22591(6) 1.06142(5) 0.01534(12) Uani d . 1
N N1 0.2717(3) 0.8577(2) 0.27383(17) 0.0153(4) Uani d D 1
N N2 0.1383(3) 0.4698(2) 0.68281(16) 0.0116(3) Uani d . 1
N N3 0.0718(3) 0.4342(2) 0.81750(16) 0.0118(3) Uani d D 1
N N4 0.1492(3) 0.1567(2) 0.83268(18) 0.0169(4) Uani d D 1
C C1 0.1846(3) 0.8475(3) 0.4006(2) 0.0151(4) Uani d . 1
H H1 0.1266 0.9415 0.4320 0.018 Uiso calc R 1
C C2 0.3383(3) 0.6981(2) 0.2626(2) 0.0122(4) Uani d . 1
C C3 0.4355(3) 0.6471(3) 0.1529(2) 0.0142(4) Uani d . 1
H H3 0.4641 0.7265 0.0687 0.017 Uiso calc R 1
C C4 0.4889(3) 0.4765(3) 0.1711(2) 0.0131(4) Uani d . 1
H H4 0.5573 0.4359 0.0990 0.016 Uiso calc R 1
C C5 0.4422(3) 0.3633(2) 0.2960(2) 0.0127(4) Uani d . 1
C C6 0.3464(3) 0.4108(2) 0.40581(19) 0.0118(4) Uani d . 1
H H6 0.3184 0.3300 0.4893 0.014 Uiso calc R 1
C C7 0.2917(3) 0.5832(2) 0.38933(19) 0.0109(4) Uani d . 1
C C8 0.1921(3) 0.6825(2) 0.4770(2) 0.0120(4) Uani d . 1
C C9 0.1249(3) 0.6266(2) 0.6176(2) 0.0127(4) Uani d . 1
H H9 0.0693 0.7074 0.6633 0.015 Uiso calc R 1
C C10 0.0822(3) 0.2737(2) 0.8937(2) 0.0123(4) Uani d . 1
H H1N 0.254(5) 0.953(2) 0.207(2) 0.028(7) Uiso d D 1
H H3N 0.037(4) 0.510(2) 0.858(2) 0.013(6) Uiso d D 1
H H4N1 0.137(4) 0.0533(17) 0.876(2) 0.023(7) Uiso d D 1
H H4N2 0.173(5) 0.190(4) 0.7452(11) 0.035(8) Uiso d D 1
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 0.02971(15) 0.01243(12) 0.02039(12) -0.00512(9) 0.00410(9) -0.00765(8)
S1 0.0217(3) 0.0111(2) 0.0101(2) -0.0029(2) 0.00152(19) -0.00200(18)
N1 0.0190(10) 0.0104(8) 0.0119(8) -0.0022(7) 0.0015(7) -0.0005(6)
N2 0.0105(8) 0.0144(8) 0.0100(8) -0.0056(6) 0.0021(6) -0.0034(6)
N3 0.0154(9) 0.0112(8) 0.0091(7) -0.0032(7) 0.0020(6) -0.0051(6)
N4 0.0239(10) 0.0117(8) 0.0144(8) -0.0050(7) 0.0044(7) -0.0056(7)
C1 0.0176(11) 0.0133(9) 0.0127(9) -0.0021(8) 0.0005(8) -0.0045(8)
C2 0.0120(10) 0.0108(9) 0.0134(9) -0.0032(7) -0.0023(8) -0.0025(7)
C3 0.0121(10) 0.0167(10) 0.0119(9) -0.0036(8) -0.0015(8) -0.0022(7)
C4 0.0109(10) 0.0174(10) 0.0111(9) -0.0028(8) -0.0020(7) -0.0049(7)
C5 0.0113(10) 0.0106(9) 0.0165(9) -0.0031(7) -0.0014(8) -0.0042(7)
C6 0.0102(10) 0.0124(9) 0.0117(9) -0.0030(7) -0.0017(7) -0.0021(7)
C7 0.0090(10) 0.0132(9) 0.0103(9) -0.0028(7) -0.0012(7) -0.0032(7)
C8 0.0114(10) 0.0116(9) 0.0131(9) -0.0035(8) -0.0011(7) -0.0037(7)
C9 0.0107(10) 0.0137(9) 0.0133(9) -0.0024(8) -0.0003(8) -0.0049(7)
C10 0.0103(10) 0.0129(9) 0.0130(9) -0.0029(7) 0.0001(7) -0.0038(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C5 1.9032(19)
S1 C10 1.699(2)
N1 C1 1.359(3)
N1 C2 1.378(3)
N1 H1N 0.878(10)
N2 C9 1.284(3)
N2 N3 1.378(2)
N3 C10 1.339(3)
N3 H3N 0.876(10)
N4 C10 1.331(3)
N4 H4N1 0.880(10)
N4 H4N2 0.873(10)
C1 C8 1.376(3)
C1 H1 0.9500
C2 C3 1.388(3)
C2 C7 1.418(3)
C3 C4 1.379(3)
C3 H3 0.9500
C4 C5 1.399(3)
C4 H4 0.9500
C5 C6 1.372(3)
C6 C7 1.398(3)
C6 H6 0.9500
C7 C8 1.447(3)
C8 C9 1.437(3)
C9 H9 0.9500
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 C2 109.25(17)
C1 N1 H1N 122.5(19)
C2 N1 H1N 126.2(18)
C9 N2 N3 115.12(17)
C10 N3 N2 119.25(16)
C10 N3 H3N 117.5(16)
N2 N3 H3N 122.8(16)
C10 N4 H4N1 119.9(17)
C10 N4 H4N2 118.1(19)
H4N1 N4 H4N2 120(3)
N1 C1 C8 110.69(18)
N1 C1 H1 124.7
C8 C1 H1 124.7
N1 C2 C3 129.70(18)
N1 C2 C7 107.45(17)
C3 C2 C7 122.85(18)
C4 C3 C2 117.27(18)
C4 C3 H3 121.4
C2 C3 H3 121.4
C3 C4 C5 119.81(18)
C3 C4 H4 120.1
C5 C4 H4 120.1
C6 C5 C4 123.94(18)
C6 C5 Br1 118.76(15)
C4 C5 Br1 117.30(15)
C5 C6 C7 117.04(18)
C5 C6 H6 121.5
C7 C6 H6 121.5
C6 C7 C2 119.09(17)
C6 C7 C8 134.17(18)
C2 C7 C8 106.75(17)
C1 C8 C9 124.92(18)
C1 C8 C7 105.86(17)
C9 C8 C7 129.10(18)
N2 C9 C8 121.41(18)
N2 C9 H9 119.3
C8 C9 H9 119.3
N4 C10 N3 117.36(18)
N4 C10 S1 122.58(16)
N3 C10 S1 120.06(15)
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
C9 N2 N3 C10 -179.30(19)
C2 N1 C1 C8 0.5(3)
C1 N1 C2 C3 180.0(2)
C1 N1 C2 C7 -0.6(2)
N1 C2 C3 C4 178.9(2)
C7 C2 C3 C4 -0.6(3)
C2 C3 C4 C5 0.8(3)
C3 C4 C5 C6 -0.8(3)
C3 C4 C5 Br1 179.01(16)
C4 C5 C6 C7 0.6(3)
Br1 C5 C6 C7 -179.25(15)
C5 C6 C7 C2 -0.3(3)
C5 C6 C7 C8 -179.8(2)
N1 C2 C7 C6 -179.18(18)
C3 C2 C7 C6 0.3(3)
N1 C2 C7 C8 0.4(2)
C3 C2 C7 C8 179.9(2)
N1 C1 C8 C9 176.0(2)
N1 C1 C8 C7 -0.2(3)
C6 C7 C8 C1 179.4(2)
C2 C7 C8 C1 -0.2(2)
C6 C7 C8 C9 3.4(4)
C2 C7 C8 C9 -176.2(2)
N3 N2 C9 C8 178.80(19)
C1 C8 C9 N2 -179.4(2)
C7 C8 C9 N2 -4.0(4)
N2 N3 C10 N4 -2.8(3)
N2 N3 C10 S1 177.10(15)
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<i>n</i> S1 1_564 0.880(10) 2.60(2) 3.390(2) 150(3) yes
N3 H3<i>n</i> S1 2_567 0.880(10) 2.650(10) 3.508(2) 167(2) yes
N4 H4<i>n</i>1 S1 2_557 0.880(10) 2.740(10) 3.569(2) 158(2) yes