#------------------------------------------------------------------------------
#$Date: 2018-10-05 15:19:55 +0300 (Fri, 05 Oct 2018) $
#$Revision: 211332 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/33/2213367.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_2213367
loop_
_publ_author_name
'Ali, Hapipah M.'
'Yusnita, Juahir'
'Ng, Seik Weng'
_publ_section_title
;
 2'-(5-Bromo-1H-indol-3-ylmethylene)benzenesulfonohydrazine
;
_journal_coeditor_code           HB2389
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2733
_journal_page_last               o2733
_journal_paper_doi               10.1107/S1600536807019927
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C15 H12 Br N3 O2 S'
_chemical_formula_moiety         'C15 H12 Br N3 O2 S'
_chemical_formula_sum            'C15 H12 Br N3 O2 S'
_chemical_formula_weight         378.25
_chemical_name_systematic
;
2'-(5-Bromo-1H-indol-3-ylmethylene)benzenesulfonohydrazine
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   33.1196(4)
_cell_length_b                   8.92600(10)
_cell_length_c                   9.91580(10)
_cell_measurement_reflns_used    9228
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      33.5
_cell_measurement_theta_min      2.4
_cell_volume                     2931.36(6)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEXII (Bruker, 2004)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 1.00
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'medium-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_sigmaI/netI    0.0110
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            59138
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.23
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.957
_exptl_absorpt_correction_T_max  0.384
_exptl_absorpt_correction_T_min  0.330
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            'Faint yellow'
_exptl_crystal_density_diffrn    1.714
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.41
_refine_diff_density_min         -0.39
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.07
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         3375
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.07
_refine_ls_R_factor_all          0.028
_refine_ls_R_factor_gt           0.027
_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/[σ²(Fo²)+(0.0433P)²+4.5513P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.081
_refine_ls_wR_factor_ref         0.082
_reflns_number_gt                3270
_reflns_number_total             3375
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2389.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_atom_sites_solution_hydrogens' value 'difmap and geom' was changed
to 'mixed'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_database_code               2213367
_cod_database_fobs_code          2213367
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'
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 0.517836(6) 0.70758(2) 0.45443(2) 0.02107(9) Uani d . 1
S S1 0.702481(14) 0.49278(5) 0.24367(5) 0.01426(11) Uani d . 1
O O1 0.70538(5) 0.58662(18) 0.12640(15) 0.0204(3) Uani d . 1
O O2 0.72824(5) 0.36427(18) 0.25464(16) 0.0226(3) Uani d . 1
N N1 0.71431(5) 0.59551(19) 0.37560(17) 0.0140(3) Uani d D 1
H H1N 0.7194(9) 0.536(3) 0.443(2) 0.031(8) Uiso d D 1
N N2 0.68493(5) 0.70889(18) 0.40448(18) 0.0132(3) Uani d . 1
N N3 0.64834(5) 1.0919(2) 0.68965(18) 0.0180(4) Uani d D 1
H H3N 0.6499(9) 1.164(2) 0.749(2) 0.026(7) Uiso d D 1
C C1 0.65175(6) 0.4387(2) 0.2608(2) 0.0151(4) Uani d . 1
C C2 0.62208(7) 0.5210(2) 0.1940(2) 0.0189(4) Uani d . 1
H H2 0.6293 0.6011 0.1357 0.023 Uiso calc R 1
C C3 0.58184(7) 0.4838(3) 0.2140(2) 0.0252(5) Uani d . 1
H H3 0.5612 0.5398 0.1705 0.030 Uiso calc R 1
C C4 0.57173(7) 0.3650(3) 0.2974(2) 0.0283(5) Uani d . 1
H H4 0.5441 0.3404 0.3113 0.034 Uiso calc R 1
C C5 0.60142(8) 0.2821(3) 0.3604(2) 0.0276(5) Uani d . 1
H H5 0.5941 0.1996 0.4157 0.033 Uiso calc R 1
C C6 0.64192(7) 0.3184(3) 0.3435(2) 0.0217(4) Uani d . 1
H H6 0.6624 0.2622 0.3875 0.026 Uiso calc R 1
C C7 0.69757(6) 0.8008(2) 0.4945(2) 0.0136(4) Uani d . 1
H H7 0.7251 0.7987 0.5215 0.016 Uiso calc R 1
C C8 0.67028(6) 0.9073(2) 0.55495(19) 0.0144(4) Uani d . 1
C C9 0.68164(6) 1.0224(2) 0.6400(2) 0.0168(4) Uani d . 1
H H9A 0.7087 1.0489 0.6606 0.020 Uiso calc R 1
C C10 0.61404(6) 1.0226(2) 0.6410(2) 0.0149(4) Uani d . 1
C C11 0.57348(6) 1.0512(2) 0.6664(2) 0.0179(4) Uani d . 1
H H11 0.5655 1.1323 0.7223 0.021 Uiso calc R 1
C C12 0.54506(6) 0.9581(2) 0.6078(2) 0.0173(4) Uani d . 1
H H12 0.5171 0.9745 0.6233 0.021 Uiso calc R 1
C C13 0.55780(6) 0.8393(2) 0.5253(2) 0.0152(4) Uani d . 1
C C14 0.59775(6) 0.8105(2) 0.4965(2) 0.0135(4) Uani d . 1
H H14 0.6054 0.7299 0.4394 0.016 Uiso calc R 1
C C15 0.62673(6) 0.9053(2) 0.55482(19) 0.0132(4) Uani d . 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
O2 S1 O1 119.23(10)
O2 S1 N1 104.12(9)
O1 S1 N1 107.63(9)
O2 S1 C1 110.00(10)
O1 S1 C1 107.60(10)
N1 S1 C1 107.71(9)
N2 N1 S1 113.01(13)
N2 N1 H1N 114(2)
S1 N1 H1N 108(2)
C7 N2 N1 111.66(16)
C9 N3 C10 109.67(17)
C9 N3 H3N 122.2(19)
C10 N3 H3N 127.9(19)
C6 C1 C2 121.5(2)
C6 C1 S1 119.57(17)
C2 C1 S1 118.92(16)
C3 C2 C1 118.9(2)
C3 C2 H2 120.6
C1 C2 H2 120.6
C2 C3 C4 120.0(2)
C2 C3 H3 120.0
C4 C3 H3 120.0
C5 C4 C3 120.5(2)
C5 C4 H4 119.7
C3 C4 H4 119.7
C4 C5 C6 120.5(2)
C4 C5 H5 119.7
C6 C5 H5 119.7
C5 C6 C1 118.5(2)
C5 C6 H6 120.8
C1 C6 H6 120.8
N2 C7 C8 120.41(19)
N2 C7 H7 119.8
C8 C7 H7 119.8
C9 C8 C15 106.38(18)
C9 C8 C7 124.99(19)
C15 C8 C7 128.18(18)
N3 C9 C8 109.91(18)
N3 C9 H9A 125.0
C8 C9 H9A 125.0
N3 C10 C11 130.53(19)
N3 C10 C15 107.34(17)
C11 C10 C15 122.12(19)
C12 C11 C10 118.13(19)
C12 C11 H11 120.9
C10 C11 H11 120.9
C11 C12 C13 119.59(18)
C11 C12 H12 120.2
C13 C12 H12 120.2
C14 C13 C12 123.36(19)
C14 C13 Br1 118.43(15)
C12 C13 Br1 118.18(15)
C13 C14 C15 117.34(18)
C13 C14 H14 121.3
C15 C14 H14 121.3
C14 C15 C10 119.42(18)
C14 C15 C8 133.76(18)
C10 C15 C8 106.69(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C13 1.905(2)
S1 O2 1.4337(16)
S1 O1 1.4363(15)
S1 N1 1.6448(17)
S1 C1 1.756(2)
N1 N2 1.433(2)
N1 H1N 0.872(10)
N2 C7 1.282(3)
N3 C9 1.358(3)
N3 C10 1.381(3)
N3 H3N 0.876(10)
C1 C6 1.390(3)
C1 C2 1.394(3)
C2 C3 1.388(3)
C2 H2 0.9500
C3 C4 1.386(4)
C3 H3 0.9500
C4 C5 1.380(4)
C4 H4 0.9500
C5 C6 1.390(3)
C5 H5 0.9500
C6 H6 0.9500
C7 C8 1.442(3)
C7 H7 0.9500
C8 C9 1.381(3)
C8 C15 1.442(3)
C9 H9A 0.9500
C10 C11 1.390(3)
C10 C15 1.416(3)
C11 C12 1.383(3)
C11 H11 0.9500
C12 C13 1.405(3)
C12 H12 0.9500
C13 C14 1.378(3)
C14 C15 1.404(3)
C14 H14 0.9500
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
N1 H1n O1 7_566 0.870(10) 2.17(2) 2.986(2) 155(3)
N3 H3n N2 7_576 0.880(10) 2.24(2) 3.028(2) 150(3)
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
O2 S1 N1 N2 -164.15(13)
O1 S1 N1 N2 68.38(15)
C1 S1 N1 N2 -47.37(16)
S1 N1 N2 C7 -170.42(14)
O2 S1 C1 C6 32.1(2)
O1 S1 C1 C6 163.45(17)
N1 S1 C1 C6 -80.77(18)
O2 S1 C1 C2 -149.89(16)
O1 S1 C1 C2 -18.54(19)
N1 S1 C1 C2 97.24(17)
C6 C1 C2 C3 1.8(3)
S1 C1 C2 C3 -176.16(16)
C1 C2 C3 C4 -1.1(3)
C2 C3 C4 C5 -0.5(3)
C3 C4 C5 C6 1.4(4)
C4 C5 C6 C1 -0.7(3)
C2 C1 C6 C5 -0.9(3)
S1 C1 C6 C5 177.05(17)
N1 N2 C7 C8 -169.22(17)
N2 C7 C8 C9 -171.7(2)
N2 C7 C8 C15 17.1(3)
C10 N3 C9 C8 1.3(2)
C15 C8 C9 N3 -1.0(2)
C7 C8 C9 N3 -173.81(19)
C9 N3 C10 C11 178.1(2)
C9 N3 C10 C15 -1.0(2)
N3 C10 C11 C12 -177.0(2)
C15 C10 C11 C12 1.9(3)
C10 C11 C12 C13 -0.1(3)
C11 C12 C13 C14 -1.2(3)
C11 C12 C13 Br1 176.74(16)
C12 C13 C14 C15 0.7(3)
Br1 C13 C14 C15 -177.22(14)
C13 C14 C15 C10 1.1(3)
C13 C14 C15 C8 176.2(2)
N3 C10 C15 C14 176.72(17)
C11 C10 C15 C14 -2.4(3)
N3 C10 C15 C8 0.3(2)
C11 C10 C15 C8 -178.80(19)
C9 C8 C15 C14 -175.2(2)
C7 C8 C15 C14 -2.7(4)
C9 C8 C15 C10 0.4(2)
C7 C8 C15 C10 172.88(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21185142
