#------------------------------------------------------------------------------
#$Date: 2025-08-19 14:52:15 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301804 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/56/2215667.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_2215667
loop_
_publ_author_name
'Jia-Jia Wei'
'Wei-Dong Wang'
'Wen-Ying Li'
'Hong-Wu He'
_publ_section_title
4-(2-Chlorobenzylidenehydrazinocarbonyl)-2-methyl-2H-pyrazole-3-sulfonamide
_journal_coeditor_code           SJ2353
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4057
_journal_page_last               o4057
_journal_paper_doi               10.1107/S1600536807044054
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C12 H12 Cl N5 O3 S'
_chemical_formula_moiety         'C12 H12 Cl N5 O3 S'
_chemical_formula_sum            'C12 H12 Cl N5 O3 S'
_chemical_formula_weight         341.78
_chemical_name_systematic
;
4-(2-Chlorobenzylidenehydrazinocarbonyl)-2-methyl-2H-pyrazole-3-sulfonic
acid amide
;
_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                89.5250(10)
_cell_angle_beta                 66.8520(10)
_cell_angle_gamma                87.7220(10)
_cell_formula_units_Z            2
_cell_length_a                   8.4272(6)
_cell_length_b                   9.0905(7)
_cell_length_c                   10.4381(7)
_cell_measurement_reflns_used    2721
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      28.25
_cell_measurement_theta_min      2.24
_cell_volume                     734.66(9)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXTL (Sheldrick, 2001)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0510
_diffrn_reflns_av_sigmaI/netI    0.0437
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4684
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.12
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.422
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.291
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2843
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0428
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0737P)²+0.1888P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1219
_refine_ls_wR_factor_ref         0.1362
_reflns_number_gt                2421
_reflns_number_total             2843
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj2353.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'None' changed to 'none' 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:

'_exptl_absorpt_correction_type' value 'None' changed to 'none'
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 
;
_cod_database_code               2215667
_cod_database_fobs_code          2215667
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
C C1 1.4090(3) 0.9541(3) -0.1318(3) 0.0513(6) Uani d . 1
H H1A 1.4523 1.0053 -0.2188 0.077 Uiso calc R 1
H H1B 1.4896 0.8758 -0.1332 0.077 Uiso calc R 1
H H1C 1.3944 1.0214 -0.0572 0.077 Uiso calc R 1
C C2 1.1438(3) 0.8013(2) -0.0105(2) 0.0305(4) Uani d . 1
C C3 0.9973(3) 0.7766(2) -0.0376(2) 0.0324(5) Uani d . 1
C C4 1.0236(3) 0.8610(3) -0.1570(2) 0.0403(5) Uani d . 1
H H4 0.9460 0.8673 -0.2004 0.048 Uiso calc R 1
C C5 0.8395(3) 0.6899(2) 0.0232(2) 0.0356(5) Uani d . 1
C C6 0.6552(3) 0.4574(3) 0.3040(2) 0.0414(5) Uani d . 1
H H6 0.7386 0.4629 0.3411 0.050 Uiso calc R 1
C C7 0.5040(3) 0.3680(3) 0.3721(2) 0.0425(5) Uani d . 1
C C8 0.4960(4) 0.2636(3) 0.4734(3) 0.0520(7) Uani d . 1
C C9 0.3514(5) 0.1801(3) 0.5337(3) 0.0724(10) Uani d . 1
H H9 0.3483 0.1104 0.6003 0.087 Uiso calc R 1
C C10 0.2140(5) 0.1986(4) 0.4970(4) 0.0782(11) Uani d . 1
H H10 0.1185 0.1408 0.5373 0.094 Uiso calc R 1
C C11 0.2164(4) 0.3036(4) 0.3995(3) 0.0703(9) Uani d . 1
H H11 0.1214 0.3182 0.3760 0.084 Uiso calc R 1
C C12 0.3606(3) 0.3868(3) 0.3372(3) 0.0521(6) Uani d . 1
H H12 0.3620 0.4565 0.2710 0.062 Uiso calc R 1
Cl Cl1 0.66414(13) 0.23836(9) 0.52817(8) 0.0729(3) Uani d . 1
N N1 1.2424(2) 0.8929(2) -0.11050(19) 0.0377(4) Uani d . 1
N N2 1.1702(3) 0.9306(2) -0.2012(2) 0.0451(5) Uani d . 1
N N3 0.8156(3) 0.6116(2) 0.1381(2) 0.0413(5) Uani d . 1
H H3A 0.894(4) 0.615(3) 0.174(3) 0.050 Uiso d . 1
N N4 0.6715(2) 0.5276(2) 0.1936(2) 0.0393(4) Uani d . 1
N N5 1.3822(3) 0.6394(3) 0.0437(3) 0.0551(6) Uani d . 1
H H5A 1.371(4) 0.572(4) 0.004(3) 0.066 Uiso d . 1
H H5B 1.475(4) 0.675(4) 0.028(3) 0.066 Uiso d . 1
O O1 1.0830(2) 0.6507(2) 0.2113(2) 0.0637(6) Uani d . 1
O O2 1.2641(2) 0.8658(2) 0.17484(19) 0.0550(5) Uani d . 1
O O3 0.7372(2) 0.6923(2) -0.03414(19) 0.0569(5) Uani d . 1
S S1 1.21556(7) 0.74039(6) 0.12003(6) 0.0396(2) 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'
O O 0.0106 0.0060 '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'
Cl Cl 0.1484 0.1585 '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
N1 C1 H1A 109.5
N1 C1 H1B 109.5
H1A C1 H1B 109.5
N1 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
N1 C2 C3 106.98(18)
N1 C2 S1 119.13(15)
C3 C2 S1 133.89(16)
C2 C3 C4 103.20(18)
C2 C3 C5 137.5(2)
C4 C3 C5 119.3(2)
N2 C4 C3 112.9(2)
N2 C4 H4 123.6
C3 C4 H4 123.6
O3 C5 N3 122.8(2)
O3 C5 C3 118.8(2)
N3 C5 C3 118.38(19)
N4 C6 C7 119.6(2)
N4 C6 H6 120.2
C7 C6 H6 120.2
C12 C7 C8 117.7(2)
C12 C7 C6 119.9(2)
C8 C7 C6 122.4(3)
C9 C8 C7 120.5(3)
C9 C8 Cl1 118.7(2)
C7 C8 Cl1 120.9(2)
C10 C9 C8 120.9(3)
C10 C9 H9 119.5
C8 C9 H9 119.5
C9 C10 C11 119.9(3)
C9 C10 H10 120.0
C11 C10 H10 120.0
C12 C11 C10 119.8(3)
C12 C11 H11 120.1
C10 C11 H11 120.1
C11 C12 C7 121.1(3)
C11 C12 H12 119.5
C7 C12 H12 119.5
N2 N1 C2 112.22(17)
N2 N1 C1 117.85(19)
C2 N1 C1 129.9(2)
C4 N2 N1 104.69(18)
C5 N3 N4 118.87(19)
C5 N3 H3A 117.9(18)
N4 N3 H3A 123.2(18)
C6 N4 N3 115.7(2)
S1 N5 H5A 116(2)
S1 N5 H5B 117(2)
H5A N5 H5B 124(3)
O2 S1 O1 119.36(12)
O2 S1 N5 108.30(12)
O1 S1 N5 108.40(14)
O2 S1 C2 107.99(10)
O1 S1 C2 105.91(10)
N5 S1 C2 106.13(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.465(3)
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
C2 N1 1.353(3)
C2 C3 1.397(3)
C2 S1 1.772(2)
C3 C4 1.404(3)
C3 C5 1.484(3)
C4 N2 1.323(3)
C4 H4 0.9300
C5 O3 1.227(3)
C5 N3 1.340(3)
C6 N4 1.274(3)
C6 C7 1.466(3)
C6 H6 0.9300
C7 C12 1.397(4)
C7 C8 1.398(3)
C8 C9 1.386(4)
C8 Cl1 1.731(3)
C9 C10 1.360(5)
C9 H9 0.9300
C10 C11 1.384(5)
C10 H10 0.9300
C11 C12 1.384(4)
C11 H11 0.9300
C12 H12 0.9300
N1 N2 1.347(3)
N3 N4 1.381(3)
N3 H3A 0.87(3)
N5 S1 1.575(2)
N5 H5A 0.77(3)
N5 H5B 0.82(3)
O1 S1 1.4292(19)
O2 S1 1.4235(18)
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 O1 . 0.87(3) 1.83(3) 2.685(3) 166(3) yes
N5 H5B O3 1_655 0.82(3) 2.05(3) 2.835(3) 160(3) yes
N5 H5A N4 2_765 0.77(3) 2.42(3) 3.105(3) 149(3) yes
N5 H5A O3 2_765 0.77(3) 2.58(3) 3.231(3) 144(3) 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
N1 C2 C3 C4 -0.4(2)
S1 C2 C3 C4 179.24(18)
N1 C2 C3 C5 178.8(2)
S1 C2 C3 C5 -1.6(4)
C2 C3 C4 N2 0.3(3)
C5 C3 C4 N2 -178.99(19)
C2 C3 C5 O3 -177.8(2)
C4 C3 C5 O3 1.2(3)
C2 C3 C5 N3 1.8(4)
C4 C3 C5 N3 -179.2(2)
N4 C6 C7 C12 -15.3(3)
N4 C6 C7 C8 165.4(2)
C12 C7 C8 C9 1.5(4)
C6 C7 C8 C9 -179.2(2)
C12 C7 C8 Cl1 -177.30(19)
C6 C7 C8 Cl1 2.0(3)
C7 C8 C9 C10 -0.6(4)
Cl1 C8 C9 C10 178.2(3)
C8 C9 C10 C11 -1.0(5)
C9 C10 C11 C12 1.6(5)
C10 C11 C12 C7 -0.7(5)
C8 C7 C12 C11 -0.9(4)
C6 C7 C12 C11 179.8(2)
C3 C2 N1 N2 0.3(2)
S1 C2 N1 N2 -179.38(15)
C3 C2 N1 C1 180.0(2)
S1 C2 N1 C1 0.3(3)
C3 C4 N2 N1 -0.2(3)
C2 N1 N2 C4 -0.1(3)
C1 N1 N2 C4 -179.8(2)
O3 C5 N3 N4 1.2(4)
C3 C5 N3 N4 -178.40(19)
C7 C6 N4 N3 178.6(2)
C5 N3 N4 C6 -179.1(2)
N1 C2 S1 O2 49.18(19)
C3 C2 S1 O2 -130.4(2)
N1 C2 S1 O1 178.13(18)
C3 C2 S1 O1 -1.4(3)
N1 C2 S1 N5 -66.77(19)
C3 C2 S1 N5 113.7(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21184161
2 PubChem 139073236
