#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/16/2231619.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_2231619
loop_
_publ_author_name
'A. Alhadi, Abeer'
'Khaledi, Hamid'
'Mohd Ali, Hapipah'
_publ_section_title
;
 3,4,5-Trihydroxybenzohydrazidium
 perchlorate--3,4,5-trihydroxybenzohydrazide--water (1/1/1)
;
_journal_coeditor_code           LX2194
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2229
_journal_page_last               o2230
_journal_paper_doi               10.1107/S1600536811030595
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C7 H9 N2 O4 +, Cl O4 -, C7 H8 N2 O4, H2 O'
_chemical_formula_moiety         'C7 H9 N2 O4 +, Cl O4 -, C7 H8 N2 O4, H2 O'
_chemical_formula_sum            'C14 H19 Cl N4 O13'
_chemical_formula_weight         486.78
_chemical_name_common
;
3,4,5-Trihydroxybenzohydrazidium perchlorate--3,4,5-trihydroxybenzohydrazide--
water (1/1/1)
;
_chemical_name_systematic
;
(3,4,5-Trihydroxybenzamido)ammonium
perchlorate--3,4,5-trihydroxybenzohydrazide--water (1/1/1)
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.1213(7)
_cell_length_b                   12.9178(4)
_cell_length_c                   7.0122(2)
_cell_measurement_reflns_used    1227
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.98
_cell_measurement_theta_min      3.15
_cell_volume                     1822.63(10)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII 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  0.0918
_diffrn_reflns_av_sigmaI/netI    0.0770
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            14383
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.57
_exptl_absorpt_coefficient_mu    0.297
_exptl_absorpt_correction_T_max  0.9912
_exptl_absorpt_correction_T_min  0.9569
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.774
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.532
_refine_ls_abs_structure_details 'Flack (1983), 1545 Friedel pairs'
_refine_ls_abs_structure_Flack   0.28(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         3393
_refine_ls_number_restraints     22
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0488
_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)+(0.0535P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0992
_refine_ls_wR_factor_ref         0.1086
_reflns_number_gt                2653
_reflns_number_total             3393
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lx2194.cif
_cod_data_source_block           I
_cod_database_code               2231619
_cod_database_fobs_code          2231619
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, 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_symmetry_multiplicity
O O1 0.47204(14) 0.7004(2) 0.1226(4) 0.0100(7) Uani d . 1 2
O O2 0.74400(13) 0.8918(2) 0.1487(5) 0.0141(7) Uani d D 1 2
H H2O 0.722(2) 0.945(2) 0.133(8) 0.021 Uiso d D 1 2
O O3 0.78618(15) 0.7058(2) 0.2858(4) 0.0107(7) Uani d D 1 2
H H3O 0.795(2) 0.652(2) 0.343(6) 0.016 Uiso d D 1 2
O O4 0.70017(14) 0.5426(2) 0.3081(4) 0.0121(7) Uani d D 1 2
H H4O 0.6714(18) 0.496(3) 0.301(7) 0.018 Uiso d D 1 2
N N1 0.42795(17) 0.8931(3) 0.1273(5) 0.0095(8) Uani d D 1 2
H H1A 0.4015(19) 0.856(3) 0.054(5) 0.011 Uiso d D 1 2
H H1B 0.416(2) 0.880(3) 0.247(3) 0.011 Uiso d D 1 2
N N2 0.49692(17) 0.8702(3) 0.1213(6) 0.0119(9) Uani d D 1 2
H H2N 0.5225(18) 0.921(2) 0.155(7) 0.014 Uiso d D 1 2
C C1 0.5142(2) 0.7687(3) 0.1322(6) 0.0104(9) Uani d . 1 2
C C2 0.58680(19) 0.7498(3) 0.1540(7) 0.0075(8) Uani d . 1 2
C C3 0.6324(2) 0.8282(3) 0.1261(6) 0.0107(9) Uani d . 1 2
H H3 0.6182 0.8929 0.0760 0.013 Uiso calc R 1 2
C C4 0.6987(2) 0.8133(3) 0.1707(6) 0.0089(9) Uani d . 1 2
C C5 0.7199(2) 0.7175(3) 0.2372(6) 0.0097(9) Uani d . 1 2
C C6 0.6750(2) 0.6371(3) 0.2535(6) 0.0097(9) Uani d U 1 2
C C7 0.6085(2) 0.6524(3) 0.2159(6) 0.0101(9) Uani d . 1 2
H H7 0.5776 0.5974 0.2317 0.012 Uiso calc R 1 2
O O5 0.46214(14) 0.4747(2) 0.3255(4) 0.0143(7) Uani d . 1 2
O O6 0.23020(14) 0.1848(2) 0.2092(4) 0.0150(8) Uani d D 1 2
H H6O 0.2019(19) 0.218(3) 0.268(6) 0.022 Uiso d D 1 2
O O7 0.32391(15) 0.0490(2) 0.1104(5) 0.0153(7) Uani d D 1 2
H H7O 0.2861(14) 0.045(4) 0.162(7) 0.023 Uiso d D 1 2
O O8 0.44941(15) 0.1051(2) 0.0634(5) 0.0140(7) Uani d D 1 2
H H8O 0.4886(12) 0.125(3) 0.071(7) 0.021 Uiso d D 1 2
N N3 0.3796(2) 0.6259(3) 0.3853(5) 0.0119(8) Uani d D 1 2
H H3A 0.3444(16) 0.666(3) 0.360(6) 0.014 Uiso d D 1 2
H H3B 0.4158(16) 0.643(4) 0.314(6) 0.014 Uiso d D 1 2
H H3C 0.394(2) 0.631(4) 0.509(3) 0.014 Uiso d D 1 2
N N4 0.35607(18) 0.5261(3) 0.3343(5) 0.0119(8) Uani d D 1 2
H H4N 0.3207(15) 0.531(4) 0.264(6) 0.014 Uiso d D 1 2
C C8 0.4038(2) 0.4525(3) 0.2963(6) 0.0111(10) Uani d . 1 2
C C9 0.3795(2) 0.3506(3) 0.2357(6) 0.0114(9) Uani d . 1 2
C C10 0.3123(2) 0.3228(3) 0.2482(6) 0.0095(9) Uani d . 1 2
H H10 0.2800 0.3717 0.2883 0.011 Uiso calc R 1 2
C C11 0.2938(2) 0.2221(3) 0.2007(6) 0.0104(10) Uani d . 1 2
C C12 0.3409(2) 0.1510(3) 0.1452(7) 0.0110(9) Uani d . 1 2
C C13 0.4064(2) 0.1793(3) 0.1252(6) 0.0119(9) Uani d . 1 2
C C14 0.4260(2) 0.2797(3) 0.1712(6) 0.0122(10) Uani d . 1 2
H H14 0.4713 0.2994 0.1583 0.015 Uiso calc R 1 2
O O9 0.59168(16) 0.4012(2) 0.2777(5) 0.0151(8) Uani d D 1 2
H H9A 0.596(3) 0.344(2) 0.334(7) 0.023 Uiso d D 1 2
H H9B 0.5591(17) 0.432(3) 0.325(7) 0.023 Uiso d D 1 2
Cl Cl1 0.61543(5) 0.11830(8) 0.15644(16) 0.0126(2) Uani d . 1 2
O O10 0.67545(14) 0.0734(2) 0.0667(4) 0.0114(7) Uani d . 1 2
O O11 0.57866(15) 0.1783(2) 0.0090(4) 0.0131(7) Uani d . 1 2
O O12 0.63558(14) 0.1903(2) 0.3124(4) 0.0103(7) Uani d . 1 2
O O13 0.57257(14) 0.0391(2) 0.2378(4) 0.0116(7) Uani d . 1 2
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'
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
C4 O2 H2O 105(3)
C5 O3 H3O 115(3)
C6 O4 H4O 112(3)
N2 N1 H1A 117(3)
N2 N1 H1B 104(3)
H1A N1 H1B 107(4)
C1 N2 N1 116.8(3)
C1 N2 H2N 124(3)
N1 N2 H2N 115(3)
O1 C1 N2 120.9(4)
O1 C1 C2 124.5(3)
N2 C1 C2 114.6(4)
C3 C2 C7 119.8(4)
C3 C2 C1 121.2(4)
C7 C2 C1 119.0(4)
C2 C3 C4 120.4(4)
C2 C3 H3 119.8
C4 C3 H3 119.8
O2 C4 C3 120.8(4)
O2 C4 C5 119.5(4)
C3 C4 C5 119.8(4)
C6 C5 O3 121.8(4)
C6 C5 C4 119.8(4)
O3 C5 C4 118.4(4)
O4 C6 C7 122.5(4)
O4 C6 C5 116.7(4)
C7 C6 C5 120.8(4)
C6 C7 C2 119.3(4)
C6 C7 H7 120.3
C2 C7 H7 120.3
C11 O6 H6O 119(3)
C12 O7 H7O 102(3)
C13 O8 H8O 111(3)
N4 N3 H3A 102(3)
N4 N3 H3B 110(3)
H3A N3 H3B 113(4)
N4 N3 H3C 114(3)
H3A N3 H3C 113(4)
H3B N3 H3C 104(4)
C8 N4 N3 116.3(4)
C8 N4 H4N 121(3)
N3 N4 H4N 110(3)
O5 C8 N4 118.3(4)
O5 C8 C9 125.2(4)
N4 C8 C9 116.3(4)
C14 C9 C10 120.1(4)
C14 C9 C8 117.6(4)
C10 C9 C8 122.2(4)
C11 C10 C9 118.9(4)
C11 C10 H10 120.6
C9 C10 H10 120.6
O6 C11 C12 114.9(4)
O6 C11 C10 124.6(4)
C12 C11 C10 120.4(4)
C13 C12 C11 120.7(4)
C13 C12 O7 118.2(4)
C11 C12 O7 121.1(4)
O8 C13 C12 117.0(4)
O8 C13 C14 123.2(4)
C12 C13 C14 119.7(4)
C9 C14 C13 120.0(4)
C9 C14 H14 120.0
C13 C14 H14 120.0
H9A O9 H9B 108(5)
O13 Cl1 O10 112.02(17)
O13 Cl1 O11 110.14(18)
O10 Cl1 O11 108.30(18)
O13 Cl1 O12 108.18(18)
O10 Cl1 O12 109.52(18)
O11 Cl1 O12 108.63(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.227(5)
O2 C4 1.372(5)
O2 H2O 0.826(19)
O3 C5 1.384(5)
O3 H3O 0.82(2)
O4 C6 1.376(5)
O4 H4O 0.839(19)
N1 N2 1.420(5)
N1 H1A 0.880(19)
N1 H1B 0.891(19)
N2 C1 1.358(5)
N2 H2N 0.863(19)
C1 C2 1.488(6)
C2 C3 1.381(6)
C2 C7 1.401(6)
C3 C4 1.384(6)
C3 H3 0.9500
C4 C5 1.389(6)
C5 C6 1.382(6)
C6 C7 1.379(6)
C7 H7 0.9500
O5 C8 1.226(5)
O6 C11 1.368(5)
O6 H6O 0.82(2)
O7 C12 1.382(5)
O7 H7O 0.843(19)
O8 C13 1.362(5)
O8 H8O 0.830(19)
N3 N4 1.420(5)
N3 H3A 0.892(19)
N3 H3B 0.911(19)
N3 H3C 0.919(19)
N4 C8 1.377(6)
N4 H4N 0.867(19)
C8 C9 1.467(6)
C9 C14 1.385(6)
C9 C10 1.402(6)
C10 C11 1.393(6)
C10 H10 0.9500
C11 C12 1.376(6)
C12 C13 1.375(6)
C13 C14 1.393(6)
C14 H14 0.9500
O9 H9A 0.85(2)
O9 H9B 0.83(2)
Cl1 O13 1.455(3)
Cl1 O10 1.480(3)
Cl1 O11 1.489(3)
Cl1 O12 1.492(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
N1 H1A O12 2_664 0.880(19) 1.95(3) 2.769(5) 155(4)
N1 H1B O11 2_665 0.891(19) 1.99(3) 2.835(5) 159(4)
N2 H2N O13 1_565 0.863(19) 1.92(2) 2.783(4) 175(4)
O2 H2O O10 1_565 0.826(19) 1.96(2) 2.782(4) 173(5)
N3 H3A O3 3_465 0.892(19) 2.10(2) 2.958(5) 161(4)
N3 H3B O1 . 0.911(19) 1.90(2) 2.788(5) 163(4)
N3 H3C O9 2_665 0.919(19) 1.95(2) 2.833(5) 160(4)
O3 H3O O4 . 0.82(2) 2.39(5) 2.732(4) 106(4)
O3 H3O O10 4_655 0.82(2) 1.96(3) 2.720(4) 153(4)
N4 H4N O2 3_465 0.867(19) 2.01(3) 2.811(5) 154(4)
O4 H4O O9 . 0.839(19) 2.02(2) 2.854(4) 171(5)
O6 H6O O12 3_455 0.82(2) 1.81(3) 2.598(4) 160(5)
O7 H7O O6 . 0.843(19) 2.15(4) 2.667(4) 119(4)
O7 H7O O4 3_455 0.843(19) 2.31(3) 3.085(4) 154(4)
O8 H8O O11 . 0.830(19) 1.99(2) 2.794(4) 164(5)
O8 H8O O13 . 0.830(19) 2.34(4) 2.892(4) 125(4)
O9 H9A O12 . 0.85(2) 2.14(3) 2.875(4) 145(5)
O9 H9A O1 2_665 0.85(2) 2.51(5) 3.036(4) 121(4)
O9 H9B O5 . 0.83(2) 2.03(3) 2.794(4) 152(5)
C3 H3 O13 1_565 0.95 2.39 3.079(5) 129.4
C7 H7 O9 . 0.95 2.57 3.291(5) 132.8
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656959
2 PubChem 139081912
