#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/98/2229842.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_2229842
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Asik, Safra Izuani Jama'
'Razak, Ibrahim Abdul'
'Shetty, Shobhitha'
'Kalluraya, Balakrishna'
_publ_section_title
;
 3-Methyl-5-oxo-4-(2-phenylhydrazinylidene)-4,5-dihydro-1H-pyrazole-1-carbothioamide
;
_journal_coeditor_code           SJ5118
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o928
_journal_paper_doi               10.1107/S1600536811009779
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C11 H11 N5 O S'
_chemical_formula_moiety         'C11 H11 N5 O S'
_chemical_formula_sum            'C11 H11 N5 O S'
_chemical_formula_weight         261.31
_chemical_name_systematic
;
3-Methyl-5-oxo-4-(2-phenylhydrazinylidene)-4,5-dihydro-1H-pyrazole-1-
carbothioamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 121.0580(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.73880(10)
_cell_length_b                   16.1103(3)
_cell_length_c                   11.3575(2)
_cell_measurement_reflns_used    5770
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      31.93
_cell_measurement_theta_min      2.45
_cell_volume                     1213.00(4)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0274
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16258
_diffrn_reflns_theta_full        32.59
_diffrn_reflns_theta_max         32.59
_diffrn_reflns_theta_min         2.45
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.262
_exptl_absorpt_correction_T_max  0.9669
_exptl_absorpt_correction_T_min  0.8739
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.391
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         4393
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0485
_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)+(0.0587P)²+0.2537P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1200
_refine_ls_wR_factor_ref         0.1350
_reflns_number_gt                3037
_reflns_number_total             4393
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj5118.cif
_cod_data_source_block           I
_cod_original_cell_volume        1213.00(3)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2229842
_cod_database_fobs_code          2229842
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
S S1 0.35472(10) 0.29034(2) 0.30227(5) 0.07026(19) Uani d . 1 . .
O O1 0.36818(17) 0.14963(6) 0.49606(10) 0.0434(2) Uani d . 1 . .
N N1 0.26541(17) 0.00165(7) 0.57723(11) 0.0346(2) Uani d . 1 . .
H H1B 0.3036 0.0523 0.5989 0.041 Uiso d R 1 . .
N N2 0.23279(17) -0.02868(7) 0.46071(11) 0.0340(2) Uani d . 1 . .
N N3 0.25183(18) 0.05536(7) 0.18342(11) 0.0340(2) Uani d . 1 . .
N N4 0.30783(17) 0.12552(6) 0.27173(11) 0.0324(2) Uani d . 1 . .
N N5 0.3303(2) 0.19488(8) 0.10601(13) 0.0478(3) Uani d . 1 . .
H H5B 0.3161 0.1470 0.0685 0.057 Uiso d R 1 . .
H H5C 0.3439 0.2384 0.0678 0.057 Uiso d R 1 . .
C C1 0.2876(2) -0.01706(10) 0.79423(14) 0.0413(3) Uani d . 1 . .
H H1A 0.3376 0.0367 0.8182 0.050 Uiso calc R 1 . .
C C2 0.2625(3) -0.06542(11) 0.88499(15) 0.0494(4) Uani d . 1 . .
H H2A 0.2961 -0.0441 0.9703 0.059 Uiso calc R 1 . .
C C3 0.1883(3) -0.14496(11) 0.84978(17) 0.0509(4) Uani d . 1 . .
H H3A 0.1732 -0.1775 0.9115 0.061 Uiso calc R 1 . .
C C4 0.1363(3) -0.17618(10) 0.72246(19) 0.0523(4) Uani d . 1 . .
H H4A 0.0839 -0.2296 0.6983 0.063 Uiso calc R 1 . .
C C5 0.1611(2) -0.12903(9) 0.62989(16) 0.0433(3) Uani d . 1 . .
H H5A 0.1272 -0.1505 0.5446 0.052 Uiso calc R 1 . .
C C6 0.23757(19) -0.04923(8) 0.66727(13) 0.0337(3) Uani d . 1 . .
C C7 0.25637(19) 0.01943(7) 0.37735(12) 0.0308(2) Uani d . 1 . .
C C8 0.31689(19) 0.10634(8) 0.39492(12) 0.0313(3) Uani d . 1 . .
C C9 0.2218(2) -0.00556(8) 0.24546(13) 0.0328(3) Uani d . 1 . .
C C10 0.1592(3) -0.08981(9) 0.18412(16) 0.0481(4) Uani d . 1 . .
H H10A 0.0995 -0.0862 0.0863 0.072 Uiso calc R 1 . .
H H10B 0.0625 -0.1121 0.2046 0.072 Uiso calc R 1 . .
H H10C 0.2751 -0.1255 0.2219 0.072 Uiso calc R 1 . .
C C11 0.3313(2) 0.20147(8) 0.22208(14) 0.0356(3) 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'
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
N2 N1 C6 . . 119.64(11) ?
N2 N1 H1B . . 120.2 ?
C6 N1 H1B . . 120.2 ?
C7 N2 N1 . . 119.04(11) ?
C9 N3 N4 . . 107.04(10) ?
C11 N4 C8 . . 130.31(11) ?
C11 N4 N3 . . 117.83(10) ?
C8 N4 N3 . . 111.70(10) ?
C11 N5 H5B . . 120.0 ?
C11 N5 H5C . . 120.0 ?
H5B N5 H5C . . 120.0 ?
C2 C1 C6 . . 119.56(14) ?
C2 C1 H1A . . 120.2 ?
C6 C1 H1A . . 120.2 ?
C3 C2 C1 . . 120.38(15) ?
C3 C2 H2A . . 119.8 ?
C1 C2 H2A . . 119.8 ?
C2 C3 C4 . . 119.73(14) ?
C2 C3 H3A . . 120.1 ?
C4 C3 H3A . . 120.1 ?
C3 C4 C5 . . 120.96(16) ?
C3 C4 H4A . . 119.5 ?
C5 C4 H4A . . 119.5 ?
C6 C5 C4 . . 118.63(15) ?
C6 C5 H5A . . 120.7 ?
C4 C5 H5A . . 120.7 ?
C1 C6 C5 . . 120.73(13) ?
C1 C6 N1 . . 118.13(12) ?
C5 C6 N1 . . 121.13(12) ?
N2 C7 C9 . . 124.65(12) ?
N2 C7 C8 . . 128.73(12) ?
C9 C7 C8 . . 106.61(10) ?
O1 C8 N4 . . 129.69(12) ?
O1 C8 C7 . . 127.07(12) ?
N4 C8 C7 . . 103.20(10) ?
N3 C9 C7 . . 111.42(11) ?
N3 C9 C10 . . 122.83(12) ?
C7 C9 C10 . . 125.75(12) ?
C9 C10 H10A . . 109.5 ?
C9 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C9 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
N5 C11 N4 . . 113.45(11) ?
N5 C11 S1 . . 124.20(10) ?
N4 C11 S1 . . 122.34(10) ?
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 C11 . 1.6560(13) ?
O1 C8 . 1.2218(15) ?
N1 N2 . 1.3073(15) ?
N1 C6 . 1.4111(16) ?
N1 H1B . 0.8600 ?
N2 C7 . 1.3072(16) ?
N3 C9 . 1.2972(17) ?
N3 N4 . 1.4222(14) ?
N4 C11 . 1.3979(16) ?
N4 C8 . 1.3988(16) ?
N5 C11 . 1.3185(18) ?
N5 H5B . 0.8602 ?
N5 H5C . 0.8600 ?
C1 C2 . 1.383(2) ?
C1 C6 . 1.3863(19) ?
C1 H1A . 0.9300 ?
C2 C3 . 1.377(3) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.380(3) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.389(2) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.387(2) ?
C5 H5A . 0.9300 ?
C7 C9 . 1.4366(17) ?
C7 C8 . 1.4572(17) ?
C9 C10 . 1.4880(19) ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
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 H1B O1 . 0.86 2.16 2.8147(16) 132 yes
N5 H5C O1 4_565 0.86 2.03 2.8806(15) 172 yes
C1 H1A S1 4_566 0.93 2.80 3.6838(16) 159 yes
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
C6 N1 N2 C7 . . . . 179.04(11) ?
C9 N3 N4 C11 . . . . -174.52(12) ?
C9 N3 N4 C8 . . . . 1.36(15) ?
C6 C1 C2 C3 . . . . -0.1(2) ?
C1 C2 C3 C4 . . . . -0.8(3) ?
C2 C3 C4 C5 . . . . 1.2(3) ?
C3 C4 C5 C6 . . . . -0.7(2) ?
C2 C1 C6 C5 . . . . 0.6(2) ?
C2 C1 C6 N1 . . . . -179.84(13) ?
C4 C5 C6 C1 . . . . -0.2(2) ?
C4 C5 C6 N1 . . . . -179.78(13) ?
N2 N1 C6 C1 . . . . 175.36(12) ?
N2 N1 C6 C5 . . . . -5.05(19) ?
N1 N2 C7 C9 . . . . -178.74(12) ?
N1 N2 C7 C8 . . . . 0.1(2) ?
C11 N4 C8 O1 . . . . -8.5(2) ?
N3 N4 C8 O1 . . . . 176.27(13) ?
C11 N4 C8 C7 . . . . 173.49(13) ?
N3 N4 C8 C7 . . . . -1.73(14) ?
N2 C7 C8 O1 . . . . 4.4(2) ?
C9 C7 C8 O1 . . . . -176.61(13) ?
N2 C7 C8 N4 . . . . -177.54(13) ?
C9 C7 C8 N4 . . . . 1.46(13) ?
N4 N3 C9 C7 . . . . -0.33(15) ?
N4 N3 C9 C10 . . . . 179.58(13) ?
N2 C7 C9 N3 . . . . 178.31(12) ?
C8 C7 C9 N3 . . . . -0.73(15) ?
N2 C7 C9 C10 . . . . -1.6(2) ?
C8 C7 C9 C10 . . . . 179.36(14) ?
C8 N4 C11 N5 . . . . 174.38(13) ?
N3 N4 C11 N5 . . . . -10.64(18) ?
C8 N4 C11 S1 . . . . -6.4(2) ?
N3 N4 C11 S1 . . . . 168.56(10) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 23927004
