#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/58/2225814.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_2225814
loop_
_publ_author_name
'Dolzhenko, Anna V.'
'Dolzhenko, Anton V.'
'Tan, Geok Kheng'
'Koh, Lip Lin'
'Pastorin, Giorgia'
_publ_section_title
;
 N'-Acetyl-5-amino-1-methyl-1H-pyrazole-4-carbohydrazonamide
 dihydrate
;
_journal_coeditor_code           CI5086
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1209
_journal_page_last               o1210
_journal_paper_doi               10.1107/S1600536810015357
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C7 H12 N6 O, 2H2 O'
_chemical_formula_moiety         'C7 H12 N6 O, 2(H2 O)'
_chemical_formula_sum            'C7 H16 N6 O3'
_chemical_formula_weight         232.26
_chemical_melting_point          513
_chemical_name_systematic
;
N'-Acetyl-5-amino-1-methyl-1H-pyrazole-4-carbohydrazonamide
dihydrate
;
_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                102.645(2)
_cell_angle_beta                 101.440(2)
_cell_angle_gamma                110.810(2)
_cell_formula_units_Z            2
_cell_length_a                   7.5496(9)
_cell_length_b                   7.6208(9)
_cell_length_c                   11.2518(13)
_cell_measurement_reflns_used    1515
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      3.03
_cell_volume                     562.75(12)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXS97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'φ and 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  0.0213
_diffrn_reflns_av_sigmaI/netI    0.0413
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3963
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.01
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.9892
_exptl_absorpt_correction_T_min  0.9528
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2001)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Rod
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.255
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2548
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0523
_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)+(0.0711P)²+0.1961P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1348
_refine_ls_wR_factor_ref         0.1414
_reflns_number_gt                2174
_reflns_number_total             2548
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci5086.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 
;
_cod_original_cell_volume        562.75(11)
_cod_database_code               2225814
_cod_database_fobs_code          2225814
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.3615(2) 0.89463(19) 0.14623(12) 0.0421(4) Uani d . 1 . .
N N1 0.7337(2) 0.3950(2) 0.48625(14) 0.0306(4) Uani d . 1 . .
N N2 0.7791(2) 0.5933(2) 0.51428(13) 0.0264(3) Uani d . 1 . .
N N3 0.7066(3) 0.8221(2) 0.42298(16) 0.0302(4) Uani d . 1 . .
H H31 0.748(3) 0.907(3) 0.495(2) 0.036(6) Uiso d . 1 . .
H H32 0.613(3) 0.821(3) 0.365(2) 0.039(6) Uiso d . 1 . .
N N4 0.3308(2) 0.2471(2) 0.11287(15) 0.0297(4) Uani d . 1 . .
H H41 0.350(3) 0.158(3) 0.132(2) 0.032(5) Uiso d . 1 . .
H H42 0.260(3) 0.223(3) 0.034(2) 0.040(6) Uiso d . 1 . .
N N5 0.4378(2) 0.5945(2) 0.18078(13) 0.0294(4) Uani d . 1 . .
N N6 0.3198(2) 0.5816(2) 0.06398(13) 0.0267(3) Uani d . 1 . .
H H6N 0.269(3) 0.479(3) 0.000(2) 0.037(6) Uiso d . 1 . .
C C1 0.6808(2) 0.6344(2) 0.41838(15) 0.0239(4) Uani d . 1 . .
C C2 0.5664(2) 0.4541(2) 0.32050(15) 0.0236(4) Uani d . 1 . .
C C3 0.6068(3) 0.3143(3) 0.37018(16) 0.0272(4) Uani d . 1 . .
H H3 0.5496 0.1780 0.3256 0.033 Uiso calc R 1 . .
C C4 0.9204(3) 0.7328(3) 0.63443(17) 0.0359(4) Uani d . 1 . .
H H4A 1.0140 0.8443 0.6188 0.054 Uiso calc R 1 . .
H H4C 0.9916 0.6687 0.6766 0.054 Uiso calc R 1 . .
H H4D 0.8504 0.7791 0.6886 0.054 Uiso calc R 1 . .
C C5 0.4374(2) 0.4304(2) 0.19753(15) 0.0225(3) Uani d . 1 . .
C C6 0.2965(3) 0.7431(3) 0.05365(16) 0.0278(4) Uani d . 1 . .
C C7 0.1873(3) 0.7318(3) -0.07661(17) 0.0354(4) Uani d . 1 . .
H H7A 0.0729 0.7603 -0.0721 0.053 Uiso calc R 1 . .
H H7B 0.1431 0.6000 -0.1353 0.053 Uiso calc R 1 . .
H H7C 0.2751 0.8278 -0.1066 0.053 Uiso calc R 1 . .
O O1W 0.8443(2) 0.7733(2) 0.15574(13) 0.0380(4) Uani d . 1 . .
H H1W 0.752(5) 0.757(4) 0.186(3) 0.069(9) Uiso d . 1 . .
H H2W 0.949(5) 0.780(4) 0.213(3) 0.065(8) Uiso d . 1 . .
O O2W 0.1806(2) 0.8169(2) 0.34309(14) 0.0393(4) Uani d . 1 . .
H H3W 0.253(4) 0.812(4) 0.294(3) 0.064(9) Uiso d . 1 . .
H H4W 0.189(4) 0.731(4) 0.381(3) 0.060(8) Uiso 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'
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
C3 N1 N2 . . 104.63(14) ?
C1 N2 N1 . . 112.10(14) ?
C1 N2 C4 . . 127.04(15) ?
N1 N2 C4 . . 120.85(14) ?
C1 N3 H31 . . 117.5(15) ?
C1 N3 H32 . . 110.8(16) ?
H31 N3 H32 . . 119(2) ?
C5 N4 H41 . . 116.7(15) ?
C5 N4 H42 . . 123.9(15) ?
H41 N4 H42 . . 118(2) ?
C5 N5 N6 . . 117.52(14) ?
C6 N6 N5 . . 117.50(14) ?
C6 N6 H6N . . 119.6(15) ?
N5 N6 H6N . . 122.8(15) ?
N2 C1 N3 . . 122.61(15) ?
N2 C1 C2 . . 106.59(14) ?
N3 C1 C2 . . 130.72(15) ?
C1 C2 C3 . . 104.15(14) ?
C1 C2 C5 . . 125.02(15) ?
C3 C2 C5 . . 130.83(15) ?
N1 C3 C2 . . 112.53(15) ?
N1 C3 H3 . . 123.7 ?
C2 C3 H3 . . 123.7 ?
N2 C4 H4A . . 109.5 ?
N2 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
N2 C4 H4D . . 109.5 ?
H4A C4 H4D . . 109.5 ?
H4C C4 H4D . . 109.5 ?
N5 C5 N4 . . 126.14(15) ?
N5 C5 C2 . . 114.92(14) ?
N4 C5 C2 . . 118.95(15) ?
O1 C6 N6 . . 121.90(15) ?
O1 C6 C7 . . 121.68(16) ?
N6 C6 C7 . . 116.42(15) ?
C6 C7 H7A . . 109.5 ?
C6 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C6 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
H1W O1W H2W . . 110(3) ?
H3W O2W H4W . . 103(3) ?
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
O1 C6 . 1.236(2) ?
N1 C3 . 1.317(2) ?
N1 N2 . 1.372(2) ?
N2 C1 . 1.344(2) ?
N2 C4 . 1.445(2) ?
N3 C1 . 1.362(2) ?
N3 H31 . 0.83(2) ?
N3 H32 . 0.86(2) ?
N4 C5 . 1.350(2) ?
N4 H41 . 0.81(2) ?
N4 H42 . 0.88(2) ?
N5 C5 . 1.303(2) ?
N5 N6 . 1.3953(19) ?
N6 C6 . 1.330(2) ?
N6 H6N . 0.84(2) ?
C1 C2 . 1.401(2) ?
C2 C3 . 1.402(2) ?
C2 C5 . 1.459(2) ?
C3 H3 . 0.94 ?
C4 H4A . 0.97 ?
C4 H4C . 0.97 ?
C4 H4D . 0.97 ?
C6 C7 . 1.500(2) ?
C7 H7A . 0.97 ?
C7 H7B . 0.97 ?
C7 H7C . 0.97 ?
O1W H1W . 0.81(3) ?
O1W H2W . 0.89(3) ?
O2W H3W . 0.86(3) ?
O2W H4W . 0.87(3) ?
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
O2W H4W N1 2_666 0.87(3) 2.04(3) 2.884(2) 162(3)
O2W H3W O1 . 0.86(3) 2.11(3) 2.885(2) 150(3)
O1W H2W O2W 1_655 0.89(3) 1.93(3) 2.824(2) 175(3)
O1W H1W N5 . 0.81(3) 2.24(3) 2.982(2) 153(3)
N6 H6N O1W 2_665 0.84(2) 2.07(2) 2.905(2) 177(2)
N4 H42 O1W 2_665 0.88(2) 2.14(3) 2.995(2) 165(2)
N4 H41 O1 1_545 0.81(2) 2.08(2) 2.874(2) 169(2)
N3 H32 N5 . 0.86(2) 2.18(2) 2.791(2) 128(2)
N3 H31 O2W 2_676 0.83(2) 2.27(2) 3.082(2) 163(2)
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
C3 N1 N2 C1 . . . . 0.66(19) ?
C3 N1 N2 C4 . . . . -178.36(16) ?
C5 N5 N6 C6 . . . . 170.14(16) ?
N1 N2 C1 N3 . . . . -177.99(15) ?
C4 N2 C1 N3 . . . . 1.0(3) ?
N1 N2 C1 C2 . . . . -0.95(19) ?
C4 N2 C1 C2 . . . . 178.00(16) ?
N2 C1 C2 C3 . . . . 0.82(18) ?
N3 C1 C2 C3 . . . . 177.53(18) ?
N2 C1 C2 C5 . . . . -179.44(15) ?
N3 C1 C2 C5 . . . . -2.7(3) ?
N2 N1 C3 C2 . . . . -0.1(2) ?
C1 C2 C3 N1 . . . . -0.5(2) ?
C5 C2 C3 N1 . . . . 179.83(17) ?
N6 N5 C5 N4 . . . . -1.0(3) ?
N6 N5 C5 C2 . . . . 178.89(14) ?
C1 C2 C5 N5 . . . . 1.9(2) ?
C3 C2 C5 N5 . . . . -178.43(17) ?
C1 C2 C5 N4 . . . . -178.18(16) ?
C3 C2 C5 N4 . . . . 1.5(3) ?
N5 N6 C6 O1 . . . . -6.2(3) ?
N5 N6 C6 C7 . . . . 173.75(16) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656065
2 PubChem 139078761
