#------------------------------------------------------------------------------
#$Date: 2022-01-15 04:34:45 +0200 (Sat, 15 Jan 2022) $
#$Revision: 272049 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/40/2244005.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_2244005
loop_
_publ_author_name
'Subha, Veerappan'
'Seethalakshmi, Thangaraj'
'Balakrishnan, Thangavelu'
'Judith Percino, M.'
'Venkatesan, Perumal'
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of the hydrated 2:1
 adduct of piperazine-1,4-diium 3,5-dinitro-2-oxidobenzoate and piperazine
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2056989022000226
_journal_volume                  78
_journal_year                    2022
_chemical_formula_iupac
;
C4 H12 N2 2+, C7 H2 N2 O7 2-, 0.5C4 H10 N2, H2 O
;
_chemical_formula_moiety
;
C7 H2 N2 O7, C4 H12 N2, 0.5(C4 H10 N2), H2 O
;
_chemical_formula_sum            'C13 H21 N5 O8'
_chemical_formula_weight         375.35
_chemical_name_systematic
;
Bis(piperazine-1,4-diium)-3,5-dinitro-2-oxidobenzoate--piperazine (1/1)
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                116.320(5)
_cell_angle_beta                 98.878(5)
_cell_angle_gamma                98.390(5)
_cell_formula_units_Z            2
_cell_length_a                   6.6211(16)
_cell_length_b                   11.891(3)
_cell_length_c                   12.389(3)
_cell_measurement_reflns_used    2314
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.90
_cell_measurement_theta_min      3.21
_cell_volume                     838.1(4)
_computing_cell_refinement
;
APEX2 and SAINT (Bruker, 2012)
;
_computing_data_collection
;
APEX2 (Bruker, 2012)
;
_computing_data_reduction
;
SAINT and XPREP (Bruker, 2012)
;
_computing_molecular_graphics
;
Mercury (Macrae et al., 2020)
;
_computing_publication_material
;
PLATON  (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014/5 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Kappa APEXII'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0665
_diffrn_reflns_av_unetI/netI     0.0656
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15411
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.924
_diffrn_reflns_theta_min         1.893
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_T_max  0.9424
_exptl_absorpt_correction_T_min  0.8335
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2012)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.209
_refine_ls_extinction_coef       0.022(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2018/3 (Sheldrick 2015b)
;
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3265
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.1076
_refine_ls_R_factor_gt           0.0485
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0514P)²+0.1429P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1333
_reflns_number_gt                1835
_reflns_number_total             3265
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            mw2181sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        838.1(3)
_cod_database_code               2244005
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.976
_shelx_estimated_absorpt_t_max   0.982
loop_
_space_group_symop_operation_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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.2400(4) 0.4979(2) 0.4846(2) 0.0331(6) Uani d 1 . .
C C2 0.1716(4) 0.5004(2) 0.3755(2) 0.0376(6) Uani d 1 . .
H H2 0.097021 0.424987 0.303896 0.045 Uiso calc 1 . .
C C3 0.2150(4) 0.6162(3) 0.3737(2) 0.0353(6) Uani d 1 . .
C C4 0.3382(4) 0.7355(2) 0.4796(2) 0.0335(6) Uani d 1 . .
C C5 0.4064(4) 0.7254(2) 0.5918(2) 0.0303(6) Uani d 1 . .
C C6 0.3534(4) 0.6100(2) 0.5917(2) 0.0325(6) Uani d 1 . .
H H6 0.394113 0.606279 0.665144 0.039 Uiso calc 1 . .
C C7 0.5309(4) 0.8402(2) 0.7123(2) 0.0362(6) Uani d 1 . .
C C8 0.1947(4) 0.0896(2) 0.5817(2) 0.0388(7) Uani d 1 . .
H H8A 0.166572 0.172139 0.595530 0.047 Uiso calc 1 . .
H H8B 0.336846 0.105846 0.628741 0.047 Uiso calc 1 . .
C C9 -0.0406(4) -0.0246(3) 0.3735(2) 0.0379(7) Uani d 1 . .
H H9A -0.048896 -0.081723 0.286864 0.046 Uiso calc 1 . .
H H9B -0.077271 0.053723 0.379768 0.046 Uiso calc 1 . .
C C10 0.4553(5) 0.5527(3) -0.0810(3) 0.0530(8) Uani d 1 . .
H H10A 0.593339 0.595334 -0.079123 0.064 Uiso calc 1 . .
H H10B 0.351574 0.562706 -0.138468 0.064 Uiso calc 1 . .
C C11 0.5558(5) 0.5896(3) 0.1283(3) 0.0519(8) Uani d 1 . .
H H11A 0.517856 0.623969 0.207334 0.062 Uiso calc 1 . .
H H11B 0.699858 0.634402 0.142542 0.062 Uiso calc 1 . .
C C12 0.9027(5) 1.0964(3) 0.0763(3) 0.0663(9) Uani d 1 . .
H H12A 0.991252 1.127416 0.158769 0.080 Uiso calc 1 . .
H H12B 0.793302 1.143558 0.084060 0.080 Uiso calc 1 . .
C C13 0.9676(5) 0.8797(3) 0.0037(3) 0.0660(9) Uani d 1 . .
H H13A 0.899018 0.788492 -0.035061 0.079 Uiso calc 1 . .
H H13B 1.058073 0.903815 0.083872 0.079 Uiso calc 1 . .
N N1 0.1911(3) 0.3784(2) 0.4897(3) 0.0448(6) Uani d 1 . .
N N2 0.1279(4) 0.6133(3) 0.2575(2) 0.0498(6) Uani d 1 . .
N N3 0.1777(3) 0.0079(2) 0.4483(2) 0.0366(6) Uani d 1 . .
N N4 0.4177(4) 0.6159(2) 0.0429(2) 0.0492(6) Uani d 1 . .
N N5 0.8059(4) 0.9568(3) 0.0213(2) 0.0594(8) Uani d 1 . .
O O1 0.2522(3) 0.37951(19) 0.5894(2) 0.0588(6) Uani d 1 . .
O O2 0.0900(3) 0.28024(19) 0.3949(2) 0.0618(6) Uani d 1 . .
O O3 0.0716(3) 0.5083(2) 0.16184(19) 0.0659(6) Uani d 1 . .
O O4 0.1115(4) 0.7148(2) 0.25659(19) 0.0693(7) Uani d 1 . .
O O5 0.5161(3) 0.83365(19) 0.80899(17) 0.0578(6) Uani d 1 . .
O O6 0.6420(3) 0.93523(17) 0.71300(16) 0.0481(5) Uani d 1 . .
O O7 0.3856(3) 0.84047(17) 0.47722(17) 0.0499(5) Uani d 1 . .
O O8 0.5428(4) 0.8759(3) 0.1338(2) 0.0634(7) Uani d 1 . .
H H8C 0.489(6) 0.796(4) 0.102(3) 0.089(13) Uiso d 1 . .
H H8D 0.486(6) 0.928(4) 0.182(4) 0.102(16) Uiso d 1 . .
H H3A 0.267(4) 0.045(2) 0.418(3) 0.069(10) Uiso d 1 . .
H H3B 0.224(4) -0.0629(19) 0.438(2) 0.058(9) Uiso d 1 . .
H H4 0.291(3) 0.582(3) 0.039(3) 0.061(10) Uiso d 1 . .
H H5A 0.726(4) 0.943(3) 0.069(2) 0.086(12) Uiso d 1 . .
H H5B 0.712(4) 0.927(3) -0.0537(18) 0.083(12) 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
C2 C1 C6 . . 120.9(2) ?
C2 C1 N1 . . 120.0(2) ?
C6 C1 N1 . . 119.1(2) ?
C1 C2 C3 . . 119.0(2) ?
C1 C2 H2 . . 120.5 ?
C3 C2 H2 . . 120.5 ?
C2 C3 C4 . . 123.4(2) ?
C2 C3 N2 . . 116.1(2) ?
C4 C3 N2 . . 120.5(2) ?
O7 C4 C3 . . 123.7(2) ?
O7 C4 C5 . . 121.7(2) ?
C3 C4 C5 . . 114.5(2) ?
C6 C5 C4 . . 120.6(2) ?
C6 C5 C7 . . 117.2(2) ?
C4 C5 C7 . . 122.2(2) ?
C5 C6 C1 . . 121.6(2) ?
C5 C6 H6 . . 119.2 ?
C1 C6 H6 . . 119.2 ?
O6 C7 O5 . . 123.4(2) ?
O6 C7 C5 . . 120.5(2) ?
O5 C7 C5 . . 116.1(2) ?
N3 C8 C9 . 2_556 110.7(2) ?
N3 C8 H8A . . 109.5 ?
C9 C8 H8A 2_556 . 109.5 ?
N3 C8 H8B . . 109.5 ?
C9 C8 H8B 2_556 . 109.5 ?
H8A C8 H8B . . 108.1 ?
N3 C9 C8 . 2_556 110.8(2) ?
N3 C9 H9A . . 109.5 ?
C8 C9 H9A 2_556 . 109.5 ?
N3 C9 H9B . . 109.5 ?
C8 C9 H9B 2_556 . 109.5 ?
H9A C9 H9B . . 108.1 ?
N4 C10 C11 . 2_665 113.1(2) ?
N4 C10 H10A . . 109.0 ?
C11 C10 H10A 2_665 . 109.0 ?
N4 C10 H10B . . 109.0 ?
C11 C10 H10B 2_665 . 109.0 ?
H10A C10 H10B . . 107.8 ?
N4 C11 C10 . 2_665 113.3(2) ?
N4 C11 H11A . . 108.9 ?
C10 C11 H11A 2_665 . 108.9 ?
N4 C11 H11B . . 108.9 ?
C10 C11 H11B 2_665 . 108.9 ?
H11A C11 H11B . . 107.7 ?
N5 C12 C13 . 2_775 110.2(3) ?
N5 C12 H12A . . 109.6 ?
C13 C12 H12A 2_775 . 109.6 ?
N5 C12 H12B . . 109.6 ?
C13 C12 H12B 2_775 . 109.6 ?
H12A C12 H12B . . 108.1 ?
N5 C13 C12 . 2_775 110.0(3) ?
N5 C13 H13A . . 109.7 ?
C12 C13 H13A 2_775 . 109.7 ?
N5 C13 H13B . . 109.7 ?
C12 C13 H13B 2_775 . 109.7 ?
H13A C13 H13B . . 108.2 ?
O2 N1 O1 . . 122.8(2) ?
O2 N1 C1 . . 118.6(3) ?
O1 N1 C1 . . 118.5(2) ?
O3 N2 O4 . . 121.8(2) ?
O3 N2 C3 . . 118.6(2) ?
O4 N2 C3 . . 119.7(3) ?
C8 N3 C9 . . 111.2(2) ?
C8 N3 H3A . . 113.0(19) ?
C9 N3 H3A . . 109.0(18) ?
C8 N3 H3B . . 108.8(17) ?
C9 N3 H3B . . 112.4(18) ?
H3A N3 H3B . . 102.2(19) ?
C11 N4 C10 . . 110.1(2) ?
C11 N4 H4 . . 106.5(19) ?
C10 N4 H4 . . 108(2) ?
C12 N5 C13 . . 111.6(2) ?
C12 N5 H5A . . 110(2) ?
C13 N5 H5A . . 111(2) ?
C12 N5 H5B . . 111(2) ?
C13 N5 H5B . . 109(2) ?
H5A N5 H5B . . 104(2) ?
H8C O8 H8D . . 119(4) ?
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
C1 C2 . 1.373(3) ?
C1 C6 . 1.390(3) ?
C1 N1 . 1.442(3) ?
C2 C3 . 1.376(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.443(3) ?
C3 N2 . 1.448(3) ?
C4 O7 . 1.257(3) ?
C4 C5 . 1.455(3) ?
C5 C6 . 1.366(3) ?
C5 C7 . 1.503(3) ?
C6 H6 . 0.9300 ?
C7 O6 . 1.251(3) ?
C7 O5 . 1.251(3) ?
C8 N3 . 1.475(3) ?
C8 C9 2_556 1.507(3) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 N3 . 1.484(3) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 N4 . 1.461(3) ?
C10 C11 2_665 1.510(4) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 N4 . 1.460(3) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 N5 . 1.478(4) ?
C12 C13 2_775 1.497(4) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 N5 . 1.488(4) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
N1 O2 . 1.227(3) ?
N1 O1 . 1.232(3) ?
N2 O3 . 1.232(3) ?
N2 O4 . 1.233(3) ?
N3 H3A . 0.903(16) ?
N3 H3B . 0.900(16) ?
N4 H4 . 0.860(17) ?
N5 H5A . 0.900(17) ?
N5 H5B . 0.918(17) ?
O8 H8C . 0.84(4) ?
O8 H8D . 0.84(4) ?
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
O8 H8D O6 2_676 0.84(4) 1.98(4) 2.807(3) 173(4) yes
N3 H3A O6 2_666 0.903(16) 1.92(2) 2.752(3) 153(3) yes
N3 H3A O7 2_666 0.903(16) 2.33(3) 2.940(3) 125(2) yes
N3 H3B O4 1_545 0.900(16) 2.50(2) 3.142(3) 129(2) yes
N3 H3B O7 1_545 0.900(16) 1.844(18) 2.696(3) 157(3) yes
N4 H4 O3 . 0.860(17) 2.59(2) 3.304(3) 141(2) yes
N5 H5A O8 . 0.900(17) 1.83(2) 2.712(3) 166(3) yes
N5 H5B O5 1_554 0.918(17) 1.74(2) 2.637(3) 165(3) yes
O8 H8C N4 . 0.84(4) 1.88(4) 2.717(3) 169(3) yes
C8 H8A O1 . 0.97 2.49 3.369(3) 151 yes
C9 H9B O2 . 0.97 2.67 3.482(3) 141 yes
C12 H12A O2 1_665 0.97 2.58 3.455(4) 151 yes
C12 H12B O5 2_676 0.97 2.59 3.353(4) 136 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . -0.7(4) ?
N1 C1 C2 C3 . . . . 178.2(2) ?
C1 C2 C3 C4 . . . . 3.0(4) ?
C1 C2 C3 N2 . . . . -176.6(2) ?
C2 C3 C4 O7 . . . . 177.0(2) ?
N2 C3 C4 O7 . . . . -3.4(4) ?
C2 C3 C4 C5 . . . . -2.6(3) ?
N2 C3 C4 C5 . . . . 177.0(2) ?
O7 C4 C5 C6 . . . . -179.7(2) ?
C3 C4 C5 C6 . . . . -0.1(3) ?
O7 C4 C5 C7 . . . . 2.1(4) ?
C3 C4 C5 C7 . . . . -178.2(2) ?
C4 C5 C6 C1 . . . . 2.3(3) ?
C7 C5 C6 C1 . . . . -179.4(2) ?
C2 C1 C6 C5 . . . . -2.0(4) ?
N1 C1 C6 C5 . . . . 179.1(2) ?
C6 C5 C7 O6 . . . . 156.6(2) ?
C4 C5 C7 O6 . . . . -25.2(4) ?
C6 C5 C7 O5 . . . . -23.2(3) ?
C4 C5 C7 O5 . . . . 155.0(2) ?
C2 C1 N1 O2 . . . . 0.7(3) ?
C6 C1 N1 O2 . . . . 179.6(2) ?
C2 C1 N1 O1 . . . . -179.0(2) ?
C6 C1 N1 O1 . . . . -0.1(3) ?
C2 C3 N2 O3 . . . . -18.7(3) ?
C4 C3 N2 O3 . . . . 161.7(2) ?
C2 C3 N2 O4 . . . . 161.1(2) ?
C4 C3 N2 O4 . . . . -18.5(4) ?
C9 C8 N3 C9 2_556 . . . 56.3(3) ?
C8 C9 N3 C8 2_556 . . . -56.4(3) ?
C10 C11 N4 C10 2_665 . . . -52.3(3) ?
C11 C10 N4 C11 2_665 . . . 52.1(3) ?
C13 C12 N5 C13 2_775 . . . 57.4(4) ?
C12 C13 N5 C12 2_775 . . . -57.4(4) ?

_cod_database_fobs_code 2244005
