#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/77/2237739.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_2237739
loop_
_publ_author_name
'Narayanam, Nagaraju'
'Gangu, Kranthi Kumar'
'Kurra, Balakrishna'
'Mukkamala, Saratchandra Babu'
_publ_section_title
;
 Piperazine-1,4-diium bis(2,4,5-tricarboxybenzoate) dihydrate
;
_journal_coeditor_code           YK2086
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o574
_journal_page_last               o575
_journal_paper_doi               10.1107/S160053681300723X
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C4 H12 N2 2+, 2C10 H5 O8 -, 2H2 O'
_chemical_formula_moiety         'C4 H12 N2 2+, 2(C10 H5 O8 -), 2H2 O'
_chemical_formula_sum            'C24 H26 N2 O18'
_chemical_formula_weight         630.46
_chemical_melting_point          560
_chemical_name_systematic
;
Piperazine-1,4-diium bis(2,4,5-tricarboxybenzoate) 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                87.117(5)
_cell_angle_beta                 89.527(5)
_cell_angle_gamma                70.962(4)
_cell_formula_units_Z            1
_cell_length_a                   8.2521(2)
_cell_length_b                   8.4810(2)
_cell_length_c                   9.6369(2)
_cell_measurement_reflns_used    7490
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.988
_cell_measurement_theta_min      2.544
_cell_volume                     636.73(3)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics
;
ORTEP-3 for Windows
(Farrugia, 2012) and Mercury (Macrae et al.,
2008)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and DIAMOND (Brandenburg, 2007)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       'ω and φ scan'
_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  0.0279
_diffrn_reflns_av_sigmaI/netI    0.0166
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11108
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.54
_exptl_absorpt_coefficient_mu    0.144
_exptl_absorpt_correction_T_max  0.9853
_exptl_absorpt_correction_T_min  0.9453
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.644
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.198
_refine_ls_extinction_coef       0.075(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         2234
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0303
_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)+(0.0431P)²+0.2345P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0831
_refine_ls_wR_factor_ref         0.0852
_reflns_number_gt                2061
_reflns_number_total             2234
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            yk2086.cif
_cod_data_source_block           I
_cod_database_code               2237739
_cod_database_fobs_code          2237739
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_symmetry_multiplicity
C C1 0.06597(16) 0.70913(15) 0.05612(13) 0.0202(3) Uani d . 1 1
C C2 0.08629(16) 0.66166(16) -0.08067(13) 0.0219(3) Uani d . 1 1
H H2 0.0098 0.7264 -0.1480 0.026 Uiso calc R 1 1
C C3 0.21641(16) 0.52142(16) -0.12023(13) 0.0196(3) Uani d . 1 1
C C4 0.32899(16) 0.42177(15) -0.01920(13) 0.0198(3) Uani d . 1 1
C C5 0.30804(16) 0.46709(16) 0.11737(13) 0.0212(3) Uani d . 1 1
H H5 0.3824 0.3995 0.1846 0.025 Uiso calc R 1 1
C C6 0.18074(16) 0.60918(16) 0.15847(13) 0.0200(3) Uani d . 1 1
C C7 0.22375(16) 0.47981(16) -0.27035(13) 0.0217(3) Uani d . 1 1
C C8 0.47247(16) 0.27185(16) -0.05880(13) 0.0217(3) Uani d . 1 1
C C9 0.18506(17) 0.63946(17) 0.31156(14) 0.0241(3) Uani d . 1 1
C C10 -0.08355(17) 0.86608(16) 0.07812(14) 0.0244(3) Uani d . 1 1
C C11 0.5751(2) 0.1289(2) 0.4758(2) 0.0448(4) Uani d . 1 1
H H11A 0.6750 0.1621 0.4555 0.054 Uiso calc R 1 1
H H11B 0.4771 0.2293 0.4836 0.054 Uiso calc R 1 1
C C12 0.5451(2) 0.0307(2) 0.36090(17) 0.0436(4) Uani d . 1 1
N N1 0.60207(17) 0.02802(17) 0.60844(14) 0.0371(3) Uani d D 1 1
O O1 -0.08934(13) 0.95103(12) 0.18574(11) 0.0337(3) Uani d . 1 1
H H1 -0.0039 0.9062 0.2342 0.051 Uiso calc R 1 1
O O2 -0.19676(13) 0.91343(13) -0.01098(11) 0.0368(3) Uani d . 1 1
O O3 0.29608(14) 0.56784(13) -0.34862(10) 0.0327(3) Uani d . 1 1
H H3 0.2974 0.5411 -0.4293 0.049 Uiso calc R 1 1
O O4 0.16086(14) 0.38163(14) -0.31255(10) 0.0348(3) Uani d . 1 1
O O5 0.50699(13) 0.24168(13) -0.17891(10) 0.0337(3) Uani d . 1 1
O O6 0.55721(13) 0.18159(13) 0.04674(10) 0.0373(3) Uani d . 1 1
H H6 0.6341 0.1014 0.0187 0.056 Uiso calc R 1 1
O O7 0.25414(14) 0.51726(13) 0.39115(10) 0.0359(3) Uani d . 1 1
O O8 0.12443(14) 0.78708(13) 0.35313(10) 0.0339(3) Uani d . 1 1
O O9 0.10687(16) 0.23958(16) 0.41278(14) 0.0453(3) Uani d D 1 1
H H12B 0.646(3) -0.068(3) 0.352(2) 0.051(5) Uiso d . 1 1
H H12A 0.518(3) 0.099(3) 0.276(2) 0.061(6) Uiso d . 1 1
H H1A 0.700(2) -0.060(2) 0.605(2) 0.046(5) Uiso d D 1 1
H H1B 0.615(3) 0.092(3) 0.677(2) 0.064(6) Uiso d D 1 1
H H9A 0.043(3) 0.224(4) 0.479(2) 0.097(10) Uiso d D 1 1
H H9B 0.135(4) 0.323(3) 0.421(3) 0.106(11) Uiso d D 1 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
C2 C1 C6 . 118.71(11)
C2 C1 C10 . 114.30(11)
C6 C1 C10 . 126.99(12)
C3 C2 C1 . 122.32(12)
C3 C2 H2 . 118.8
C1 C2 H2 . 118.8
C2 C3 C4 . 119.08(12)
C2 C3 C7 . 117.76(11)
C4 C3 C7 . 123.09(11)
C5 C4 C3 . 118.88(11)
C5 C4 C8 . 120.72(11)
C3 C4 C8 . 120.38(11)
C4 C5 C6 . 122.85(12)
C4 C5 H5 . 118.6
C6 C5 H5 . 118.6
C5 C6 C1 . 118.16(11)
C5 C6 C9 . 114.29(11)
C1 C6 C9 . 127.54(11)
O4 C7 O3 . 124.71(12)
O4 C7 C3 . 122.38(12)
O3 C7 C3 . 112.81(11)
O5 C8 O6 . 124.18(12)
O5 C8 C4 . 121.94(12)
O6 C8 C4 . 113.86(11)
O7 C9 O8 . 122.61(12)
O7 C9 C6 . 117.42(11)
O8 C9 C6 . 119.92(12)
O2 C10 O1 . 120.53(12)
O2 C10 C1 . 118.69(12)
O1 C10 C1 . 120.74(12)
N1 C11 C12 . 110.21(13)
N1 C11 H11A . 109.6
C12 C11 H11A . 109.6
N1 C11 H11B . 109.6
C12 C11 H11B . 109.6
H11A C11 H11B . 108.1
N1 C12 C11 2_656 110.90(13)
N1 C12 H12B 2_656 107.1(11)
C11 C12 H12B . 109.1(12)
N1 C12 H12A 2_656 106.8(12)
C11 C12 H12A . 110.4(13)
H12B C12 H12A . 112.5(17)
C12 N1 C11 2_656 110.89(13)
C12 N1 H1A 2_656 110.4(12)
C11 N1 H1A . 110.1(12)
C12 N1 H1B 2_656 109.9(14)
C11 N1 H1B . 108.3(14)
H1A N1 H1B . 107.1(19)
C10 O1 H1 . 109.5
C7 O3 H3 . 109.5
C8 O6 H6 . 109.5
H9A O9 H9B . 112(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C2 . 1.3906(18)
C1 C6 . 1.4127(18)
C1 C10 . 1.5138(17)
C2 C3 . 1.3851(18)
C2 H2 . 0.9300
C3 C4 . 1.3947(18)
C3 C7 . 1.5024(17)
C4 C5 . 1.3833(18)
C4 C8 . 1.4911(17)
C5 C6 . 1.3885(18)
C5 H5 . 0.9300
C6 C9 . 1.5129(18)
C7 O4 . 1.2031(17)
C7 O3 . 1.3074(16)
C8 O5 . 1.2096(16)
C8 O6 . 1.3014(16)
C9 O7 . 1.2367(17)
C9 O8 . 1.2715(17)
C10 O2 . 1.2269(17)
C10 O1 . 1.2841(17)
C11 N1 . 1.479(2)
C11 C12 . 1.487(3)
C11 H11A . 0.9700
C11 H11B . 0.9700
C12 N1 2_656 1.478(2)
C12 H12B . 0.98(2)
C12 H12A . 0.96(2)
N1 C12 2_656 1.478(2)
N1 H1A . 0.904(15)
N1 H1B . 0.901(16)
O1 H1 . 0.8200
O3 H3 . 0.8200
O6 H6 . 0.8200
O9 H9A . 0.858(17)
O9 H9B . 0.824(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
O1 H1 O8 . 0.82 1.63 2.4225(15) 161
O3 H3 O7 1_554 0.82 1.80 2.6100(13) 167
O6 H6 O2 1_645 0.82 1.78 2.5884(13) 170
N1 H1A O9 2_656 0.904(15) 1.825(15) 2.7283(17) 175.9(18)
N1 H1B O5 1_556 0.901(16) 1.941(18) 2.7420(16) 147(2)
O9 H9A O8 2_566 0.858(17) 2.135(18) 2.9904(18) 174(3)
O9 H9B O7 . 0.824(18) 2.182(19) 2.9799(19) 163(3)
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_4
_geom_torsion
C6 C1 C2 C3 . -0.96(19)
C10 C1 C2 C3 . 179.89(12)
C1 C2 C3 C4 . 1.5(2)
C1 C2 C3 C7 . 178.63(12)
C2 C3 C4 C5 . -0.59(19)
C7 C3 C4 C5 . -177.56(12)
C2 C3 C4 C8 . -178.79(11)
C7 C3 C4 C8 . 4.23(19)
C3 C4 C5 C6 . -0.9(2)
C8 C4 C5 C6 . 177.35(12)
C4 C5 C6 C1 . 1.4(2)
C4 C5 C6 C9 . -177.56(12)
C2 C1 C6 C5 . -0.46(18)
C10 C1 C6 C5 . 178.57(12)
C2 C1 C6 C9 . 178.31(12)
C10 C1 C6 C9 . -2.7(2)
C2 C3 C7 O4 . -95.55(16)
C4 C3 C7 O4 . 81.46(17)
C2 C3 C7 O3 . 80.87(15)
C4 C3 C7 O3 . -102.12(14)
C5 C4 C8 O5 . -170.29(13)
C3 C4 C8 O5 . 7.9(2)
C5 C4 C8 O6 . 8.07(18)
C3 C4 C8 O6 . -173.75(12)
C5 C6 C9 O7 . -24.00(18)
C1 C6 C9 O7 . 157.18(13)
C5 C6 C9 O8 . 153.59(13)
C1 C6 C9 O8 . -25.2(2)
C2 C1 C10 O2 . 18.28(18)
C6 C1 C10 O2 . -160.79(13)
C2 C1 C10 O1 . -159.58(12)
C6 C1 C10 O1 . 21.4(2)
N1 C11 C12 N1 2_656 56.82(19)
C12 C11 N1 C12 2_656 -56.81(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139085436
