##############################################################################
#                                                                            #
# 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 Acta Crystallographica 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.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2011-08-19
_journal_date_accepted     2011-08-24
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2011
_journal_volume     67
_journal_issue     10
_journal_page_first     o2570
_journal_page_last     o2570
_journal_paper_category     QO
_journal_coeditor_code     LH5323
_publ_contact_author_name     'Prof. Fun, Hoong-Kun'
_publ_contact_author_address
;
      X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      MALAYSIA
;
_publ_contact_author_email     'hkfun@usm.my'
_publ_contact_author_fax     '604 6579150'
_publ_contact_author_phone     '604 6533652'
_publ_section_title
;\
4-[2-(4-Bromophenyl)hydrazinylidene]-3-methyl-5-oxo-4,5-dihydro-1H-\
pyrazole-1-carbothioamide
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Hoong-Kun Fun'
;
      Thomson Reuters ResearcherID: A-3561-2009.
;
;
      X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      Malaysia
;
    'Madhukar Hemamalini' ?
;
      X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      Malaysia
;
    'Shobhitha Shetty' ?
;
      Department of Studies in Chemistry
      Mangalore University
      Mangalagangotri
      Mangalore 574 199
      India
;
    'BalaKrishna Kalluraya' ?
;
      Department of Studies in Chemistry
      Mangalore University
      Mangalagangotri
      Mangalore 574 199
      India
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
4-[2-(4-Bromophenyl)hydrazinylidene]-3-methyl-5-oxo-4,5-dihydro-
1H-pyrazole-1-carbothioamide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C11 H10 Br N5 O S'
_chemical_formula_sum     'C11 H10 Br N5 O S'
_chemical_formula_iupac     'C11 H10 Br N5 O S'
_chemical_formula_weight     340.21
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'C 2/c'
_symmetry_space_group_name_Hall     '-C 2yc'
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'
_cell_length_a     25.6080(18)
_cell_length_b     11.6686(8)
_cell_length_c     9.0823(6)
_cell_angle_alpha     90.00
_cell_angle_beta     98.907(2)
_cell_angle_gamma     90.00
_cell_volume     2681.2(3)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     4204
_cell_measurement_theta_min     2.88
_cell_measurement_theta_max     27.83
_cell_measurement_temperature     296(2)
_exptl_crystal_description     slab
_exptl_crystal_colour     orange
_exptl_crystal_size_max     0.48
_exptl_crystal_size_mid     0.33
_exptl_crystal_size_min     0.17
_exptl_crystal_density_diffrn     1.686
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1360
_exptl_absorpt_coefficient_mu     3.221
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2009)'
_exptl_absorpt_correction_T_min     0.3058
_exptl_absorpt_correction_T_max     0.6089
_exptl_special_details     ?
_diffrn_ambient_temperature     296(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 APEXII DUO CCD area-detector
;
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     .
_diffrn_reflns_number     15576
_diffrn_reflns_av_R_equivalents     0.0338
_diffrn_reflns_av_sigmaI/netI     0.0353
_diffrn_reflns_theta_min     2.88
_diffrn_reflns_theta_max     30.00
_diffrn_reflns_theta_full     30.00
_diffrn_measured_fraction_theta_max     0.990
_diffrn_measured_fraction_theta_full     0.990
_diffrn_reflns_limit_h_min     -36
_diffrn_reflns_limit_h_max     36
_diffrn_reflns_limit_k_min     -16
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_limit_l_max     12
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     3869
_reflns_number_gt     2776
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0619
_refine_ls_R_factor_gt     0.0396
_refine_ls_wR_factor_gt     0.1106
_refine_ls_wR_factor_ref     0.1269
_refine_ls_goodness_of_fit_ref     1.030
_refine_ls_restrained_S_all     1.030
_refine_ls_number_reflns     3869
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0646P)²+2.3027P] 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     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.459
_refine_diff_density_min     -0.754
_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, 2009)'
_computing_cell_refinement     'SAINT (Bruker, 2009)'
_computing_data_reduction     'SAINT (Bruker, 2009)'
_computing_structure_solution     'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics
                             'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_publication_material
                             'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.24780(3) 0.67093(6) 0.16175(6) 0.04971(18) Uani d . 1 1 . .
    Br Br1 0.476115(14) 1.36166(3) 0.95277(4) 0.07714(17) Uani d . 1 1 . .
    O O1 0.29888(8) 0.85438(14) 0.39141(19) 0.0476(4) Uani d . 1 1 . .
    N N1 0.30362(8) 0.65467(16) 0.43648(19) 0.0377(4) Uani d . 1 1 . .
    N N2 0.32861(9) 0.58425(17) 0.5541(2) 0.0442(5) Uani d . 1 1 . .
    N N3 0.37576(9) 0.85410(17) 0.6771(2) 0.0433(4) Uani d . 1 1 . .
    N N4 0.36660(9) 0.95754(18) 0.6236(2) 0.0432(4) Uani d . 1 1 . .
    N N5 0.26122(10) 0.4932(2) 0.3443(2) 0.0483(5) Uani d . 1 1 . .
    C C1 0.35129(9) 0.7684(2) 0.6042(2) 0.0399(5) Uani d . 1 1 . .
    C C2 0.31496(9) 0.77032(19) 0.4632(2) 0.0358(4) Uani d . 1 1 . .
    C C3 0.35624(11) 0.6506(2) 0.6496(3) 0.0464(6) Uani d . 1 1 . .
    C C4 0.39352(9) 1.0510(2) 0.6975(2) 0.0398(5) Uani d . 1 1 . .
    C C5 0.43053(11) 1.0338(2) 0.8242(3) 0.0536(6) Uani d . 1 1 . .
    H H5A 0.4388 0.9600 0.8588 0.064 Uiso calc R 1 1 . .
    C C6 0.45488(11) 1.1273(3) 0.8982(3) 0.0581(7) Uani d . 1 1 . .
    H H6A 0.4794 1.1169 0.9840 0.070 Uiso calc R 1 1 . .
    C C7 0.44277(10) 1.2359(2) 0.8449(3) 0.0500(6) Uani d . 1 1 . .
    C C8 0.40611(11) 1.2539(2) 0.7174(3) 0.0517(6) Uani d . 1 1 . .
    H H8A 0.3983 1.3276 0.6818 0.062 Uiso calc R 1 1 . .
    C C9 0.38156(11) 1.1601(2) 0.6447(3) 0.0498(6) Uani d . 1 1 . .
    H H9A 0.3568 1.1705 0.5595 0.060 Uiso calc R 1 1 . .
    C C10 0.27077(9) 0.6012(2) 0.3187(2) 0.0373(5) Uani d . 1 1 . .
    C C11 0.38809(16) 0.6072(3) 0.7892(4) 0.0753(10) Uani d . 1 1 . .
    H H11A 0.3828 0.5261 0.7969 0.113 Uiso calc R 1 1 . .
    H H11B 0.3772 0.6450 0.8733 0.113 Uiso calc R 1 1 . .
    H H11C 0.4248 0.6224 0.7875 0.113 Uiso calc R 1 1 . .
    H H1N4 0.3475(14) 0.980(3) 0.548(4) 0.064(9) Uiso d . 1 1 . .
    H H1N5 0.2727(15) 0.468(3) 0.425(4) 0.077(11) Uiso d . 1 1 . .
    H H2N5 0.2458(13) 0.456(3) 0.275(4) 0.057(9) Uiso d . 1 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
    S1 0.0660(4) 0.0450(4) 0.0326(3) 0.0018(3) -0.0098(2) 0.0007(2)
    Br1 0.0707(2) 0.0514(2) 0.0982(3) -0.00776(14) -0.02193(18) -0.02813(16)
    O1 0.0595(11) 0.0342(9) 0.0437(9) 0.0036(7) -0.0085(8) 0.0020(6)
    N1 0.0453(10) 0.0322(10) 0.0316(8) -0.0025(7) -0.0064(7) 0.0006(6)
    N2 0.0550(12) 0.0331(10) 0.0387(9) -0.0027(9) -0.0111(8) 0.0047(7)
    N3 0.0467(11) 0.0381(11) 0.0420(10) -0.0061(8) -0.0032(8) -0.0022(7)
    N4 0.0470(11) 0.0362(11) 0.0422(10) -0.0034(8) -0.0064(8) -0.0040(8)
    N5 0.0642(14) 0.0411(12) 0.0341(9) -0.0113(10) -0.0092(9) -0.0014(8)
    C1 0.0442(12) 0.0366(12) 0.0350(9) -0.0020(9) -0.0055(8) -0.0002(8)
    C2 0.0408(11) 0.0326(11) 0.0327(9) 0.0001(9) 0.0018(8) -0.0002(8)
    C3 0.0529(14) 0.0399(13) 0.0406(11) -0.0057(10) -0.0112(10) 0.0037(9)
    C4 0.0388(11) 0.0379(12) 0.0411(10) -0.0039(9) 0.0012(9) -0.0064(9)
    C5 0.0528(15) 0.0406(14) 0.0599(14) 0.0007(11) -0.0151(11) -0.0046(11)
    C6 0.0519(15) 0.0527(17) 0.0606(15) 0.0019(12) -0.0203(12) -0.0123(12)
    C7 0.0441(13) 0.0413(14) 0.0609(14) -0.0045(10) -0.0036(10) -0.0158(11)
    C8 0.0554(15) 0.0351(13) 0.0600(14) -0.0030(11) -0.0053(11) -0.0044(10)
    C9 0.0531(15) 0.0413(14) 0.0492(12) -0.0033(11) -0.0104(10) -0.0018(10)
    C10 0.0412(11) 0.0388(12) 0.0301(9) -0.0009(9) -0.0006(8) -0.0038(8)
    C11 0.095(2) 0.0536(17) 0.0604(17) -0.0116(17) -0.0407(16) 0.0130(13)
_geom_special_details
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
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
    S1 C10 . 1.667(2) ?
    Br1 C7 . 1.893(2) ?
    O1 C2 . 1.214(3) ?
    N1 C2 . 1.394(3) ?
    N1 C10 . 1.401(3) ?
    N1 N2 . 1.420(3) ?
    N2 C3 . 1.289(3) ?
    N3 C1 . 1.304(3) ?
    N3 N4 . 1.308(3) ?
    N4 C4 . 1.404(3) ?
    N4 H1N4 . 0.82(3) ?
    N5 C10 . 1.311(3) ?
    N5 H1N5 . 0.81(4) ?
    N5 H2N5 . 0.81(4) ?
    C1 C3 . 1.435(3) ?
    C1 C2 . 1.462(3) ?
    C3 C11 . 1.486(3) ?
    C4 C9 . 1.377(4) ?
    C4 C5 . 1.387(3) ?
    C5 C6 . 1.378(4) ?
    C5 H5A . 0.9300 ?
    C6 C7 . 1.375(4) ?
    C6 H6A . 0.9300 ?
    C7 C8 . 1.389(4) ?
    C8 C9 . 1.379(4) ?
    C8 H8A . 0.9300 ?
    C9 H9A . 0.9300 ?
    C11 H11A . 0.9600 ?
    C11 H11B . 0.9600 ?
    C11 H11C . 0.9600 ?
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
    C2 N1 C10 . . 130.42(19) ?
    C2 N1 N2 . . 111.85(17) ?
    C10 N1 N2 . . 117.67(18) ?
    C3 N2 N1 . . 107.16(19) ?
    C1 N3 N4 . . 118.3(2) ?
    N3 N4 C4 . . 119.5(2) ?
    N3 N4 H1N4 . . 131(2) ?
    C4 N4 H1N4 . . 110(2) ?
    C10 N5 H1N5 . . 117(3) ?
    C10 N5 H2N5 . . 117(2) ?
    H1N5 N5 H2N5 . . 125(4) ?
    N3 C1 C3 . . 125.1(2) ?
    N3 C1 C2 . . 128.6(2) ?
    C3 C1 C2 . . 106.37(19) ?
    O1 C2 N1 . . 130.2(2) ?
    O1 C2 C1 . . 126.8(2) ?
    N1 C2 C1 . . 103.00(18) ?
    N2 C3 C1 . . 111.6(2) ?
    N2 C3 C11 . . 122.7(2) ?
    C1 C3 C11 . . 125.7(2) ?
    C9 C4 C5 . . 120.5(2) ?
    C9 C4 N4 . . 119.0(2) ?
    C5 C4 N4 . . 120.4(2) ?
    C6 C5 C4 . . 119.3(3) ?
    C6 C5 H5A . . 120.3 ?
    C4 C5 H5A . . 120.3 ?
    C7 C6 C5 . . 119.8(2) ?
    C7 C6 H6A . . 120.1 ?
    C5 C6 H6A . . 120.1 ?
    C6 C7 C8 . . 121.3(2) ?
    C6 C7 Br1 . . 118.24(19) ?
    C8 C7 Br1 . . 120.5(2) ?
    C9 C8 C7 . . 118.6(3) ?
    C9 C8 H8A . . 120.7 ?
    C7 C8 H8A . . 120.7 ?
    C4 C9 C8 . . 120.4(2) ?
    C4 C9 H9A . . 119.8 ?
    C8 C9 H9A . . 119.8 ?
    N5 C10 N1 . . 113.5(2) ?
    N5 C10 S1 . . 124.77(17) ?
    N1 C10 S1 . . 121.74(17) ?
    C3 C11 H11A . . 109.5 ?
    C3 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    C3 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
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
    C2 N1 N2 C3 . . . . -2.1(3) ?
    C10 N1 N2 C3 . . . . -179.5(2) ?
    C1 N3 N4 C4 . . . . -178.2(2) ?
    N4 N3 C1 C3 . . . . -178.7(2) ?
    N4 N3 C1 C2 . . . . 2.4(4) ?
    C10 N1 C2 O1 . . . . 0.6(4) ?
    N2 N1 C2 O1 . . . . -176.3(2) ?
    C10 N1 C2 C1 . . . . 179.5(2) ?
    N2 N1 C2 C1 . . . . 2.6(2) ?
    N3 C1 C2 O1 . . . . -4.0(4) ?
    C3 C1 C2 O1 . . . . 176.9(2) ?
    N3 C1 C2 N1 . . . . 177.0(3) ?
    C3 C1 C2 N1 . . . . -2.0(3) ?
    N1 N2 C3 C1 . . . . 0.7(3) ?
    N1 N2 C3 C11 . . . . 179.8(3) ?
    N3 C1 C3 N2 . . . . -178.2(3) ?
    C2 C1 C3 N2 . . . . 0.9(3) ?
    N3 C1 C3 C11 . . . . 2.6(5) ?
    C2 C1 C3 C11 . . . . -178.2(3) ?
    N3 N4 C4 C9 . . . . -176.6(2) ?
    N3 N4 C4 C5 . . . . 1.5(4) ?
    C9 C4 C5 C6 . . . . 0.8(4) ?
    N4 C4 C5 C6 . . . . -177.4(3) ?
    C4 C5 C6 C7 . . . . -0.8(5) ?
    C5 C6 C7 C8 . . . . 0.3(5) ?
    C5 C6 C7 Br1 . . . . 178.7(2) ?
    C6 C7 C8 C9 . . . . 0.3(4) ?
    Br1 C7 C8 C9 . . . . -178.1(2) ?
    C5 C4 C9 C8 . . . . -0.2(4) ?
    N4 C4 C9 C8 . . . . 178.0(2) ?
    C7 C8 C9 C4 . . . . -0.4(4) ?
    C2 N1 C10 N5 . . . . -167.1(2) ?
    N2 N1 C10 N5 . . . . 9.7(3) ?
    C2 N1 C10 S1 . . . . 13.9(4) ?
    N2 N1 C10 S1 . . . . -169.28(17) ?
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
    N4 H1N4 O1 . 0.82(4) 2.27(4) 2.788(3) 121(3) yes
    N5 H1N5 S1 6_566 0.80(4) 2.84(4) 3.522(2) 144(3) yes
    N5 H2N5 O1 4_545 0.82(3) 2.11(4) 2.925(3) 175(4) yes
