#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/11/2231101.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_2231101
loop_
_publ_author_name
'Murtaza, Shahzad'
'Hamza, Muhammad'
'Tahir, M. Nawaz'
_publ_section_title
;
 1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-aminium
 chloride--thiourea (1/1)
;
_journal_coeditor_code           GK2395
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2193
_journal_paper_doi               10.1107/S1600536811029989
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C11 H14 N3 O +, Cl -, C H4 N2 S'
_chemical_formula_moiety         'C11 H14 N3 O +, Cl -, C H4 N2 S'
_chemical_formula_sum            'C12 H18 Cl N5 O S'
_chemical_formula_weight         315.82
_chemical_name_systematic
;
1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-aminium chloride--
thiourea (1/1)
;
_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
_cell_angle_beta                 90.851(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9733(11)
_cell_length_b                   8.2572(8)
_cell_length_c                   18.859(2)
_cell_measurement_reflns_used    2948
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.40
_cell_measurement_theta_min      2.04
_cell_volume                     1552.9(3)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 7.50
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_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  0.0320
_diffrn_reflns_av_sigmaI/netI    0.0345
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            14413
_diffrn_reflns_theta_full        28.40
_diffrn_reflns_theta_max         28.40
_diffrn_reflns_theta_min         2.04
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.384
_exptl_absorpt_correction_T_max  0.950
_exptl_absorpt_correction_T_min  0.935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.303
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3876
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0393
_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)+(0.0519P)²+0.4062P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1003
_refine_ls_wR_factor_ref         0.1107
_reflns_number_gt                2948
_reflns_number_total             3876
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gk2395.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2231101
_cod_database_fobs_code          2231101
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 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_thermal_displace_type
_atom_site_occupancy
_atom_site_disorder_group
O O1 0.02683(12) 0.52568(13) 0.17891(7) 0.0429(4) Uani 1.000 -16
N N1 0.15623(14) 0.67708(15) 0.10210(8) 0.0380(4) Uani 1.000 -16
N N2 0.15254(14) 0.83360(15) 0.07471(8) 0.0395(5) Uani 1.000 -16
N N3 -0.10897(15) 0.84880(18) 0.20387(9) 0.0369(5) Uani 1.000 -16
C C1 0.22930(16) 0.55157(19) 0.06724(9) 0.0365(5) Uani 1.000 -16
C C2 0.2008(2) 0.5159(2) -0.00289(11) 0.0539(7) Uani 1.000 -16
C C3 0.2738(2) 0.3964(3) -0.03623(12) 0.0631(8) Uani 1.000 -16
C C4 0.3709(2) 0.3132(2) 0.00038(13) 0.0568(7) Uani 1.000 -16
C C5 0.3968(2) 0.3477(3) 0.07011(13) 0.0587(7) Uani 1.000 -16
C C6 0.3260(2) 0.4689(2) 0.10411(11) 0.0488(6) Uani 1.000 -16
C C7 0.05681(16) 0.65825(18) 0.15067(9) 0.0335(5) Uani 1.000 -16
C C8 -0.00154(15) 0.81326(18) 0.15630(9) 0.0328(4) Uani 1.000 -16
C C9 0.05869(16) 0.91713(19) 0.11086(9) 0.0360(5) Uani 1.000 -16
C C10 0.0318(2) 1.0926(2) 0.09755(12) 0.0506(6) Uani 1.000 -16
C C11 0.2742(2) 0.9003(2) 0.04478(12) 0.0528(7) Uani 1.000 -16
S S1 0.70196(5) 0.59619(6) 0.27908(3) 0.0490(2) Uani 1.000 -16
N N4 0.76836(16) 0.35228(19) 0.19593(9) 0.0531(6) Uani 1.000 -16
N N5 0.57194(16) 0.3262(2) 0.25376(10) 0.0579(6) Uani 1.000 -16
C C12 0.67972(17) 0.4139(2) 0.24001(10) 0.0398(5) Uani 1.000 -16
Cl Cl1 0.64868(5) 0.01267(5) 0.13661(3) 0.0476(2) Uani 1.000 -16
H H2 0.13349 0.57146 -0.02737 0.0647 Uiso 1.000 -16
H H3 0.25677 0.37259 -0.08371 0.0758 Uiso 1.000 -16
H H3A -0.148(2) 0.757(3) 0.2222(10) 0.0554 Uiso 1.000 -16
H H3B -0.084(2) 0.913(3) 0.2403(12) 0.0554 Uiso 1.000 -16
H H3C -0.185(2) 0.900(2) 0.1825(11) 0.0554 Uiso 1.000 -16
H H4 0.41951 0.23278 -0.02225 0.0681 Uiso 1.000 -16
H H5 0.46218 0.28957 0.09489 0.0704 Uiso 1.000 -16
H H6 0.34432 0.49342 0.15140 0.0586 Uiso 1.000 -16
H H10A 0.00647 1.10791 0.04870 0.0759 Uiso 1.000 -16
H H10B 0.11123 1.15417 0.10810 0.0759 Uiso 1.000 -16
H H10C -0.03966 1.12835 0.12730 0.0759 Uiso 1.000 -16
H H11A 0.34012 0.91528 0.08178 0.0791 Uiso 1.000 -16
H H11B 0.25437 1.00266 0.02288 0.0791 Uiso 1.000 -16
H H11C 0.30826 0.82695 0.00990 0.0791 Uiso 1.000 -16
H H4A 0.75487 0.25846 0.17735 0.0637 Uiso 1.000 -16
H H4B 0.83942 0.40608 0.18589 0.0637 Uiso 1.000 -16
H H5A 0.56147 0.23283 0.23429 0.0695 Uiso 1.000 -16
H H5B 0.51243 0.36276 0.28217 0.0695 Uiso 1.000 -16
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'
Cl Cl 0.1484 0.1585 ' 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
_geom_angle_publ_flag
N2 N1 C1 120.81(14) no
N2 N1 C7 109.78(12) no
C1 N1 C7 127.13(13) no
N1 N2 C9 107.49(13) no
N1 N2 C11 118.56(13) no
C9 N2 C11 126.10(13) no
H3B N3 H3C 105.7(18) no
C8 N3 H3C 115.0(13) no
C8 N3 H3A 112.9(14) no
C8 N3 H3B 113.3(13) no
H3A N3 H3B 108.2(19) no
H3A N3 H3C 100.7(17) no
H4A N4 H4B 120.00 no
C12 N4 H4A 120.00 no
C12 N4 H4B 120.00 no
H5A N5 H5B 120.00 no
C12 N5 H5A 120.00 no
C12 N5 H5B 120.00 no
N1 C1 C6 119.27(16) no
C2 C1 C6 121.05(16) no
N1 C1 C2 119.68(15) no
C1 C2 C3 119.05(18) no
C2 C3 C4 120.2(2) no
C3 C4 C5 120.3(2) no
C4 C5 C6 120.3(2) no
C1 C6 C5 119.10(19) no
N1 C7 C8 104.54(13) no
O1 C7 C8 131.16(15) no
O1 C7 N1 124.22(14) no
N3 C8 C7 122.97(14) no
C7 C8 C9 109.79(14) no
N3 C8 C9 127.24(14) no
N2 C9 C8 108.13(14) no
C8 C9 C10 129.66(16) no
N2 C9 C10 122.19(15) no
C1 C2 H2 120.00 no
C3 C2 H2 120.00 no
C2 C3 H3 120.00 no
C4 C3 H3 120.00 no
C5 C4 H4 120.00 no
C3 C4 H4 120.00 no
C4 C5 H5 120.00 no
C6 C5 H5 120.00 no
C5 C6 H6 120.00 no
C1 C6 H6 120.00 no
H10B C10 H10C 109.00 no
C9 C10 H10C 109.00 no
C9 C10 H10A 109.00 no
C9 C10 H10B 109.00 no
H10A C10 H10B 110.00 no
H10A C10 H10C 109.00 no
N2 C11 H11B 109.00 no
N2 C11 H11A 109.00 no
H11A C11 H11C 110.00 no
N2 C11 H11C 109.00 no
H11A C11 H11B 110.00 no
H11B C11 H11C 109.00 no
N4 C12 N5 117.65(16) no
S1 C12 N4 122.12(13) no
S1 C12 N5 120.22(14) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C12 1.6891(18) no
O1 C7 1.2554(19) no
N1 C1 1.432(2) no
N1 C7 1.369(2) no
N1 N2 1.3921(18) no
N2 C9 1.355(2) no
N2 C11 1.454(2) no
N3 C8 1.438(2) no
N3 H3B 0.90(2) no
N3 H3A 0.92(2) no
N3 H3C 0.952(19) no
N4 C12 1.324(2) no
N5 C12 1.325(2) no
N4 H4A 0.8600 no
N4 H4B 0.8600 no
N5 H5B 0.8600 no
N5 H5A 0.8600 no
C1 C2 1.380(3) no
C1 C6 1.364(3) no
C2 C3 1.383(3) no
C3 C4 1.366(3) no
C4 C5 1.366(3) no
C5 C6 1.387(3) no
C7 C8 1.411(2) no
C8 C9 1.359(2) no
C9 C10 1.494(2) no
C2 H2 0.9300 no
C3 H3 0.9300 no
C4 H4 0.9300 no
C5 H5 0.9300 no
C6 H6 0.9300 no
C10 H10A 0.9600 no
C10 H10B 0.9600 no
C10 H10C 0.9600 no
C11 H11A 0.9600 no
C11 H11B 0.9600 no
C11 H11C 0.9600 no
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
N3 H3A S1 1_455 0.92(2) 2.28(2) 3.1619(17) 159.9(19) yes
N3 H3B O1 2_555 0.90(2) 1.87(2) 2.764(2) 174(2) yes
N3 H3C Cl1 1_465 0.952(19) 2.08(2) 3.0316(16) 180(2) yes
N4 H4A Cl1 . 0.86 2.41 3.2404(17) 163 yes
N4 H4B O1 1_655 0.86 2.12 2.970(2) 170 yes
N5 H5A Cl1 . 0.86 2.74 3.4956(19) 148 yes
N5 H5A S1 2_645 0.86 2.87 3.3768(17) 120 yes
N5 H5B Cl1 2_655 0.86 2.56 3.4091(18) 171 yes
C10 H10B S1 2_655 0.96 2.85 3.505(2) 126 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
_geom_torsion_publ_flag
C1 N1 N2 C9 169.48(14) no
C1 N1 N2 C11 -39.5(2) no
C7 N1 N2 C9 5.48(18) no
C7 N1 N2 C11 156.51(16) no
N2 N1 C1 C2 -56.2(2) no
C7 N1 C1 C2 104.8(2) no
N2 N1 C1 C6 123.92(17) no
C7 N1 C1 C6 -75.1(2) no
N2 N1 C7 C8 -4.53(18) no
N2 N1 C7 O1 172.53(15) no
C1 N1 C7 O1 9.8(3) no
C1 N1 C7 C8 -167.26(15) no
N1 N2 C9 C10 177.29(16) no
N1 N2 C9 C8 -4.06(18) no
C11 N2 C9 C8 -152.29(17) no
C11 N2 C9 C10 29.1(3) no
N1 C1 C2 C3 178.85(17) no
C6 C1 C2 C3 -1.3(3) no
C2 C1 C6 C5 0.3(3) no
N1 C1 C6 C5 -179.83(17) no
C1 C2 C3 C4 1.2(3) no
C2 C3 C4 C5 -0.2(3) no
C3 C4 C5 C6 -0.9(3) no
C4 C5 C6 C1 0.8(3) no
O1 C7 C8 N3 5.1(3) no
O1 C7 C8 C9 -174.75(18) no
N1 C7 C8 N3 -178.19(15) no
N1 C7 C8 C9 2.02(19) no
N3 C8 C9 C10 0.0(3) no
C7 C8 C9 N2 1.30(19) no
C7 C8 C9 C10 179.82(18) no
N3 C8 C9 N2 -178.49(16) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656841
