#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/58/2225818.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_2225818
loop_
_publ_author_name
'Chernyshev, V. M.'
'Chernysheva, A. V.'
'Tarasova, E. V.'
'Ivanov, V. V.'
'Starikova, Z. A.'
_publ_section_title
;
 2-(4-Chlorobenzoyl)-1-(diaminomethylene)hydrazinium chloride
 monohydrate
;
_journal_coeditor_code           CV2710
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1152
_journal_page_last               o1153
_journal_paper_doi               10.1107/S1600536810014108
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C8 H10 Cl N4 O +, Cl -, H2 O'
_chemical_formula_moiety         'C8 H10 Cl N4 O +, Cl -, H2 O'
_chemical_formula_sum            'C8 H12 Cl2 N4 O2'
_chemical_formula_weight         267.12
_chemical_name_systematic
;
2-(4-chlorobenzoyl)-1-(diaminomethylene)hydrazinium chloride monohydrate
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.360(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.349(4)
_cell_length_b                   4.3563(9)
_cell_length_c                   14.516(3)
_cell_measurement_reflns_used    195
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      3
_cell_volume                     1195.2(4)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004) and XPREP (Bruker, 2005)'
_computing_molecular_graphics    'Mercury (Macrae et al.,  2006)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008), publCIF (Westrip, 2010) and PLATON
(Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'omega 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  0.0341
_diffrn_reflns_av_sigmaI/netI    0.0268
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9756
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.16
_exptl_absorpt_coefficient_mu    0.535
_exptl_absorpt_correction_T_max  0.924
_exptl_absorpt_correction_T_min  0.814
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.787
_refine_diff_density_min         -0.407
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.166
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2330
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.166
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0626
_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)+(0.0000P)²+7.6548P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1386
_refine_ls_wR_factor_ref         0.1419
_reflns_number_gt                2099
_reflns_number_total             2330
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv2710.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2225818
_cod_database_fobs_code          2225818
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
Cl Cl1 0.04674(6) 0.7630(4) 0.43499(8) 0.0378(3) Uani d . 1 . .
Cl Cl2 0.61291(5) 0.8080(2) 0.16436(7) 0.0176(2) Uani d . 1 . .
O O1 0.23490(15) 0.4393(7) 0.1141(2) 0.0206(6) Uani d . 1 . .
N N1 0.30500(17) 0.8203(8) 0.1875(2) 0.0167(7) Uani d . 1 . .
H H1 0.3168 0.9410 0.2387 0.020 Uiso d R 1 . .
N N2 0.36010(18) 0.7335(8) 0.1466(2) 0.0168(7) Uani d . 1 . .
H H2 0.3904 0.5813 0.1693 0.020 Uiso d R 1 . .
N N3 0.32072(18) 1.0675(8) 0.0221(2) 0.0170(7) Uani d . 1 . .
H H3B 0.2901 1.1579 0.0524 0.020 Uiso d R 1 . .
H H3A 0.3270 1.1318 -0.0344 0.020 Uiso d R 1 . .
N N4 0.41145(18) 0.7296(8) 0.0186(2) 0.0191(8) Uani d . 1 . .
H H4B 0.4390 0.5690 0.0416 0.023 Uiso d R 1 . .
H H4A 0.4156 0.8225 -0.0354 0.023 Uiso d R 1 . .
C C1 0.3636(2) 0.8462(9) 0.0616(3) 0.0151(8) Uani d . 1 . .
C C2 0.2468(2) 0.6400(10) 0.1752(3) 0.0167(8) Uani d . 1 . .
C C3 0.1974(2) 0.6938(10) 0.2392(3) 0.0189(9) Uani d . 1 . .
C C4 0.1303(2) 0.5694(12) 0.2146(3) 0.0255(10) Uani d . 1 . .
H H4 0.1166 0.4678 0.1573 0.031 Uiso calc R 1 . .
C C5 0.0832(2) 0.5933(12) 0.2738(3) 0.0288(11) Uani d . 1 . .
H H5 0.0379 0.5112 0.2564 0.035 Uiso calc R 1 . .
C C6 0.1048(2) 0.7415(12) 0.3591(3) 0.0248(10) Uani d . 1 . .
C C7 0.1710(2) 0.8685(12) 0.3853(3) 0.0294(11) Uani d . 1 . .
H H7 0.1843 0.9706 0.4426 0.035 Uiso calc R 1 . .
C C8 0.2176(2) 0.8438(12) 0.3260(3) 0.0253(10) Uani d . 1 . .
H H8 0.2627 0.9273 0.3437 0.030 Uiso calc R 1 . .
O O1W 0.48997(16) 0.3347(7) 0.1577(2) 0.0256(7) Uani d . 1 . .
H H1W 0.5036 0.1484 0.1625 0.038 Uiso d R 1 . .
H H2W 0.5283 0.4382 0.1677 0.038 Uiso d R 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'
Cl Cl 0.1484 0.1585 '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
C2 N1 N2 . . 118.8(3) ?
C2 N1 H1 . . 120.3 ?
N2 N1 H1 . . 115.6 ?
C1 N2 N1 . . 119.4(3) ?
C1 N2 H2 . . 116.6 ?
N1 N2 H2 . . 123.2 ?
C1 N3 H3B . . 121.8 ?
C1 N3 H3A . . 115.4 ?
H3B N3 H3A . . 122.7 ?
C1 N4 H4B . . 122.8 ?
C1 N4 H4A . . 116.1 ?
H4B N4 H4A . . 121.1 ?
N3 C1 N4 . . 120.9(4) ?
N3 C1 N2 . . 121.0(4) ?
N4 C1 N2 . . 118.2(4) ?
O1 C2 N1 . . 122.0(4) ?
O1 C2 C3 . . 121.0(4) ?
N1 C2 C3 . . 117.1(4) ?
C4 C3 C8 . . 118.9(4) ?
C4 C3 C2 . . 118.1(4) ?
C8 C3 C2 . . 122.8(4) ?
C3 C4 C5 . . 121.2(4) ?
C3 C4 H4 . . 119.4 ?
C5 C4 H4 . . 119.4 ?
C6 C5 C4 . . 118.6(4) ?
C6 C5 H5 . . 120.7 ?
C4 C5 H5 . . 120.7 ?
C7 C6 C5 . . 121.5(4) ?
C7 C6 Cl1 . . 119.7(3) ?
C5 C6 Cl1 . . 118.8(4) ?
C6 C7 C8 . . 119.5(4) ?
C6 C7 H7 . . 120.2 ?
C8 C7 H7 . . 120.2 ?
C7 C8 C3 . . 120.3(4) ?
C7 C8 H8 . . 119.8 ?
C3 C8 H8 . . 119.8 ?
H1W O1W H2W . . 104.3 ?
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
Cl1 C6 . 1.736(4) ?
O1 C2 . 1.232(5) ?
N1 C2 . 1.352(5) ?
N1 N2 . 1.379(4) ?
N1 H1 . 0.8999 ?
N2 C1 . 1.343(5) ?
N2 H2 . 0.9001 ?
N3 C1 . 1.321(5) ?
N3 H3B . 0.9002 ?
N3 H3A . 0.9000 ?
N4 C1 . 1.324(5) ?
N4 H4B . 0.8999 ?
N4 H4A . 0.9002 ?
C2 C3 . 1.488(5) ?
C3 C4 . 1.381(6) ?
C3 C8 . 1.398(6) ?
C4 C5 . 1.384(6) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.380(7) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.373(7) ?
C7 C8 . 1.377(6) ?
C7 H7 . 0.9300 ?
C8 H8 . 0.9300 ?
O1W H1W . 0.8517 ?
O1W H2W . 0.8542 ?
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
N1 H1 Cl2 2_655 0.900 2.359 3.194(4) 154
N2 H2 O1W 1_555 0.900 2.243 3.031(4) 146
N2 H2 Cl2 2_645 0.900 2.705 3.260(4) 121
N3 H3B O1 1_565 0.900 1.963 2.848(3) 167
N3 H3A Cl2 3_675 0.900 2.433 3.280(4) 157
N4 H4B O1W 1_555 0.900 2.035 2.834(4) 147
N4 H4A Cl2 3_675 0.900 2.441 3.286(4) 156
O1W H1W Cl2 1_545 0.852 2.579 3.292(4) 142
O1W H2W Cl2 1_555 0.854 2.304 3.134(4) 164
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 C1 . . . . 94.5(4) ?
N1 N2 C1 N3 . . . . 8.8(6) ?
N1 N2 C1 N4 . . . . -171.3(3) ?
N2 N1 C2 O1 . . . . -15.4(6) ?
N2 N1 C2 C3 . . . . 164.5(3) ?
O1 C2 C3 C4 . . . . -15.6(6) ?
N1 C2 C3 C4 . . . . 164.5(4) ?
O1 C2 C3 C8 . . . . 159.5(4) ?
N1 C2 C3 C8 . . . . -20.5(6) ?
C8 C3 C4 C5 . . . . 0.5(7) ?
C2 C3 C4 C5 . . . . 175.8(4) ?
C3 C4 C5 C6 . . . . -0.8(8) ?
C4 C5 C6 C7 . . . . 1.1(8) ?
C4 C5 C6 Cl1 . . . . -178.3(4) ?
C5 C6 C7 C8 . . . . -1.1(8) ?
Cl1 C6 C7 C8 . . . . 178.3(4) ?
C6 C7 C8 C3 . . . . 0.8(8) ?
C4 C3 C8 C7 . . . . -0.5(7) ?
C2 C3 C8 C7 . . . . -175.5(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656066
2 PubChem 139078767
