Bis(5-amino-3-carb­oxy-1H-1,2,4-triazol-4-ium) dihydrogenphosphate nitrate 5-amino-1H-1,2,4-triazol-4-ium-3-carboxyl­ate

Berrah, F.; Bouchene, R.; Bouacida, S.; Daran, J.-C.

doi:10.1107/S1600536812014481

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Pages o1333-o1334

doi:10.1107/S1600536812014481

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Bis(5-amino-3-carboxy-1H-1,2,4-triazol-4-ium) dihydrogenphosphate nitrate 5-amino-1H-1,2,4-triazol-4-ium-3-carboxylate

Fadila Berrah,^a ^*‡ Rafika Bouchene,^a ‡ Sofiane Bouacida ^b ‡ and Jean-Claude Daran ^c

^aLaboratoire de Chimie Appliquée et Technologie des Matériaux, LCATM, Université Larbi Ben M'Hidi, 04000 Oum El Bouaghi, Algeria, ^bUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale, CHEMS, Faculté des Sciences Exactes, Université Mentouri Constantine 25000, Algeria, and ^cLaboratoire de Chimie de Coodination, UPR–CNRS 8241, 205, Route de Narbonne, 31077 Toulouse cedex 04, France
^*Correspondence e-mail: fadilaber@yahoo.fr

(Received 22 March 2012; accepted 3 April 2012; online 6 April 2012)

In the title compound, 2C₃H₅N₄O₂⁺·H₂PO₄⁻·NO₃⁻·C₃H₄N₄O₂, three independent 5-amino-1H-1,2,4-triazol-3-carboxylic acid moieties are observed. Two are in the form of cations, while the third is in the zwitterionic form. The triazole rings in the two cations are almost coplanar, making an angle of 4.11 (7)°. Layers parallel to the (20-1) plane, resulting from hydrogen bonding of the organic molecules and the nitrate anions, are linked via H₂PO₄⁻ infinite zigzag chains running parallel to the c axis. The crystal studied was an inversion twin, with refined components of 0.33 (7) and 0.67 (7).

Related literature

For structural studies of related compounds, see: Berrah et al. (2011 , 2012 ); Fernandes et al. (2011 ); Ouakkaf et al. (2011 ). For hydrogen-bond motifs, see: Etter et al. (1990 ); Grell et al. (1999 ).

Experimental

Crystal data

2C₃H₅N₄O₂⁺·NO₃⁻·H₂PO₄⁻·C₃H₄N₄O₂
M_r = 545.32
Monoclinic, C c
a = 19.2249 (13) Å
b = 13.2036 (7) Å
c = 7.7468 (5) Å
β = 101.079 (7)°
V = 1929.8 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 180 K
0.45 × 0.43 × 0.16 mm

Data collection

Agilent Xcalibur Sapphire1 long-nozzle diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.832, T_max = 1.000
10050 measured reflections
3836 independent reflections
3735 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.067
S = 1.05
3836 reflections
330 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.27 e Å⁻³
Absolute structure: Flack (1983 ), 1858 Friedel pairs
Flack parameter: 0.33 (7)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1B—H3B⋯O7	0.86	2.24	3.030 (2)	152
N4C—H4C⋯O5	0.86	1.92	2.765 (2)	169
N4B—H4B⋯O6	0.86	1.92	2.780 (2)	177
O2—H2⋯O1Cⁱ	0.82	1.77	2.5563 (19)	160
N4A—H4A⋯O7	0.86	1.93	2.784 (2)	172
O1B—H1B⋯O3	0.82	1.65	2.4648 (19)	175
O4—H4⋯O3ⁱⁱ	0.82	1.92	2.671 (2)	151
O1A—H1A⋯O1ⁱⁱⁱ	0.82	1.62	2.423 (2)	166
Symmetry codes: (i) x, y-1, z; (ii) $[x, -y+2, z+{\script{1\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, y+{\script{1\over 2}}, z+1]$ .

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2002 (Burla et al., 2005 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ), ORTEP-3 for Windows (Farrugia, 1997 ) and DIAMOND (Brandenburg & Berndt, 2001 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812014481/fj2538sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812014481/fj2538Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812014481/fj2538Isup3.cml

checkCIF report

Comment top

Synthesis we have undertaken using 1,2,4-triazol derivatives and various inorganic acids (nitric, sulfuric, phosphoric acids and their mixtures) have permitted obtaining hybrids involving sulfate and nitrate anions (Berrah et al., 2012; Ouakkaf et al., 2011) and the title compound which involves a mixture of dihydrgenphosphate and nitrate anions. The comparison between networks observed in these structures make clear the influence of the anion upon the hydrogen bonds patterns encountered.

The asymmetric unit in this compound consists of two cations (A and B), one zwitterium (C), one dihydrogenphosphate anion and one nitrate anion (Fig.1). Bond distances and angles observed in the different entities, present no unusual features and are consistent with those reported previously (Berrah et al., 2011, 2012; Fernandes et al., 2011; Ouakkaf et al., 2011). The triazol rings in (A) and (B) are almost coplanar making an angle of 4.11 (7)°; while they form with the ring in (C) dihedral angles of 8.64 (5)° and 9.62 (6)° respectively.

The title compound shows a three-dimensional packing where organic molecules and nitrate anions, linked by means of O—H···O and N—H···O contacts, lie in layers stacked parallel to (20–1) plane and in which R⁶₆ (18) rings (Etter et al., 1990; Grell et al., 1999) are observed (Fig. 2) (Table 1). H₂PO₄^- anions form infinite zigzag chains running parallel to the c axis; which pass through the R⁶₆ (18) rings to connect the layers together (Fig. 3).

Related literature top

For structural studies of related compounds, see: Berrah et al. (2011, 2012); Fernandes et al. (2011); Ouakkaf et al. (2011). For hydrogen-bond motifs, see: Etter et al. (1990); Grell et al. (1999).

Experimental top

Colourless crystals of compound (I) were obtained by the slow evaporation of a water-methanol (1:1)solution of 5-amino-1,2,4 triazol-1H- 3-carboxylic acid hydrate and a mixture of nitric and phosphoric acids in a 1:1 stoichiometric ratio.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SIR2002 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg & Berndt, 2001); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The asymmetric unit of (I) with the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii. Hydrogen bonds are shown as dashed lines.
	Fig. 2. Partial packing view showing layers parallel to (20–1) plane and R⁶₆ (18) rings. Only one H₂PO₄^- is represented to show how it fills the rings. Hydrogen bonds are shown as dashed lines.
	Fig. 3. Partial packing view showing H₂PO₄^- infinite zigzag chain running parallel to [001]direction and how it links the layers together. Hydrogen bonds are shown as dashed lines.

Bis(5-amino-3-carboxy-1H-1,2,4-triazol-4-ium) dihydrogenphosphate nitrate 5-amino-1H-1,2,4-triazol-4-ium-3-carboxylate top

Crystal data top

2C₃H₅N₄O₂⁺·NO³⁻·H₂PO₄⁻·C₃H₄N₄O₂	F(000) = 1120
M_r = 545.32	D_x = 1.877 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
a = 19.2249 (13) Å	Cell parameters from 8428 reflections
b = 13.2036 (7) Å	θ = 3.1–28.3°
c = 7.7468 (5) Å	µ = 0.25 mm⁻¹
β = 101.079 (7)°	T = 180 K
V = 1929.8 (2) Å³	Box, colourless
Z = 4	0.45 × 0.43 × 0.16 mm

Data collection top

Agilent Xcalibur Sapphire1 long-nozzle diffractometer	3836 independent reflections
Radiation source: fine-focus sealed tube	3735 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
Detector resolution: 8.2632 pixels mm^-1	θ_max = 26.4°, θ_min = 3.1°
ω scans	h = −24→23
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −16→16
T_min = 0.832, T_max = 1.000	l = −9→9
10050 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.027	H-atom parameters constrained
wR(F²) = 0.067	w = 1/[σ²(F_o²) + (0.0378P)² + 0.9492P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.008
3836 reflections	Δρ_max = 0.23 e Å⁻³
330 parameters	Δρ_min = −0.27 e Å⁻³
2 restraints	Absolute structure: Flack (1983), 1858 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.33 (7)

Crystal data top

2C₃H₅N₄O₂⁺·NO³⁻·H₂PO₄⁻·C₃H₄N₄O₂	V = 1929.8 (2) Å³
M_r = 545.32	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 19.2249 (13) Å	µ = 0.25 mm⁻¹
b = 13.2036 (7) Å	T = 180 K
c = 7.7468 (5) Å	0.45 × 0.43 × 0.16 mm
β = 101.079 (7)°

Data collection top

Agilent Xcalibur Sapphire1 long-nozzle diffractometer	3836 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	3735 reflections with I > 2σ(I)
T_min = 0.832, T_max = 1.000	R_int = 0.023
10050 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	H-atom parameters constrained
wR(F²) = 0.067	Δρ_max = 0.23 e Å⁻³
S = 1.05	Δρ_min = −0.27 e Å⁻³
3836 reflections	Absolute structure: Flack (1983), 1858 Friedel pairs
330 parameters	Absolute structure parameter: 0.33 (7)
2 restraints

Special details top

Experimental. Absorption correction: empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. CrysAlisPro (Agilent Technologies, 2011)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O6	0.41566 (8)	1.31611 (10)	0.5894 (2)	0.0222 (3)
N3C	0.18588 (9)	1.43700 (13)	0.1472 (2)	0.0236 (4)
O1C	0.30311 (8)	1.62763 (11)	0.3449 (2)	0.0272 (3)
N1B	0.58554 (9)	1.25858 (12)	0.9762 (2)	0.0217 (4)
H5B	0.6216	1.2555	1.061	0.026*
H3B	0.5677	1.3164	0.9405	0.026*
N4C	0.28426 (9)	1.41292 (12)	0.3399 (2)	0.0201 (4)
H4C	0.3233	1.4265	0.4111	0.024*
N1	0.43355 (9)	1.40196 (12)	0.6489 (2)	0.0184 (3)
C3C	0.25660 (10)	1.32115 (15)	0.3022 (3)	0.0187 (4)
O2C	0.19992 (9)	1.64211 (12)	0.1575 (2)	0.0349 (4)
N2C	0.19719 (9)	1.33628 (12)	0.1833 (2)	0.0219 (4)
H2C	0.1695	1.2886	0.1356	0.026*
O7	0.48583 (8)	1.41235 (11)	0.7696 (2)	0.0276 (3)
C1C	0.24818 (11)	1.59375 (15)	0.2508 (3)	0.0215 (4)
O5	0.39976 (9)	1.47811 (11)	0.5845 (2)	0.0313 (4)
N1C	0.28090 (10)	1.23307 (13)	0.3647 (2)	0.0266 (4)
H5C	0.3198	1.2297	0.4408	0.032*
H3C	0.2579	1.1786	0.3296	0.032*
C2C	0.23928 (11)	1.48136 (15)	0.2447 (3)	0.0202 (4)
P1	0.27249 (3)	0.89899 (3)	0.30351 (6)	0.01592 (11)
O2B	0.43278 (7)	0.92432 (10)	0.59606 (18)	0.0210 (3)
N2B	0.57956 (9)	1.08016 (13)	0.9423 (2)	0.0198 (3)
H2B	0.6152	1.0654	1.0238	0.024*
N4B	0.50067 (9)	1.16518 (12)	0.7706 (2)	0.0167 (3)
H4B	0.475	1.2135	0.7182	0.02*
N3B	0.53912 (9)	1.01015 (12)	0.8405 (2)	0.0194 (3)
C2B	0.49164 (10)	1.06425 (14)	0.7377 (2)	0.0167 (4)
C3B	0.55750 (10)	1.17458 (15)	0.9007 (2)	0.0159 (4)
O3	0.30722 (7)	0.99921 (10)	0.27601 (17)	0.0198 (3)
C3A	0.47957 (10)	1.70083 (15)	0.7432 (3)	0.0186 (4)
O2	0.32459 (7)	0.81370 (10)	0.2805 (2)	0.0247 (3)
H2	0.309	0.7593	0.3072	0.037*
O1	0.20396 (9)	0.88190 (12)	0.1753 (3)	0.0359 (4)
N3A	0.56813 (9)	1.75022 (12)	0.9580 (2)	0.0189 (3)
N2A	0.51436 (9)	1.78030 (13)	0.8257 (2)	0.0202 (3)
H2A	0.5042	1.8425	0.7988	0.024*
O2A	0.65270 (7)	1.62929 (11)	1.20239 (19)	0.0233 (3)
N1A	0.42476 (10)	1.70396 (14)	0.6126 (2)	0.0266 (4)
H5A	0.4079	1.7614	0.572	0.032*
H3A	0.4058	1.6486	0.5677	0.032*
C1B	0.43737 (10)	1.01611 (14)	0.6006 (3)	0.0164 (4)
N4A	0.51196 (9)	1.61845 (12)	0.8229 (2)	0.0181 (3)
H4A	0.5014	1.5563	0.7966	0.022*
O1B	0.40060 (7)	1.08030 (10)	0.49496 (18)	0.0185 (3)
H1B	0.3709	1.05	0.4234	0.028*
O4	0.25679 (10)	0.89062 (14)	0.4902 (2)	0.0431 (5)
H4	0.2766	0.9369	0.551	0.065*
O1A	0.60814 (8)	1.49336 (11)	1.0444 (2)	0.0267 (3)
H1A	0.6426	1.4631	1.0994	0.04*
C1A	0.61377 (10)	1.58682 (15)	1.0807 (3)	0.0180 (4)
C2A	0.56512 (10)	1.65246 (15)	0.9543 (3)	0.0174 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O6	0.0208 (7)	0.0113 (6)	0.0303 (7)	−0.0030 (5)	−0.0055 (6)	−0.0021 (6)
N3C	0.0210 (9)	0.0151 (8)	0.0305 (10)	−0.0020 (7)	−0.0057 (8)	0.0017 (7)
O1C	0.0224 (8)	0.0126 (7)	0.0398 (9)	−0.0015 (6)	−0.0109 (7)	0.0016 (6)
N1B	0.0206 (9)	0.0172 (8)	0.0232 (8)	−0.0014 (7)	−0.0061 (7)	0.0008 (7)
N4C	0.0175 (9)	0.0147 (8)	0.0243 (9)	−0.0010 (6)	−0.0059 (7)	0.0012 (6)
N1	0.0166 (8)	0.0133 (8)	0.0235 (8)	0.0012 (6)	−0.0006 (7)	0.0016 (6)
C3C	0.0191 (10)	0.0172 (9)	0.0193 (9)	−0.0020 (7)	0.0020 (8)	−0.0008 (7)
O2C	0.0277 (8)	0.0176 (8)	0.0494 (10)	0.0007 (7)	−0.0172 (7)	0.0056 (7)
N2C	0.0192 (9)	0.0122 (8)	0.0302 (9)	−0.0038 (6)	−0.0056 (7)	−0.0013 (7)
O7	0.0244 (8)	0.0181 (7)	0.0326 (8)	0.0005 (6)	−0.0138 (7)	−0.0017 (6)
C1C	0.0196 (10)	0.0153 (10)	0.0273 (11)	0.0014 (8)	−0.0012 (8)	0.0028 (8)
O5	0.0286 (8)	0.0129 (7)	0.0439 (9)	0.0020 (6)	−0.0145 (7)	0.0045 (6)
N1C	0.0271 (10)	0.0136 (8)	0.0333 (10)	−0.0019 (7)	−0.0091 (8)	0.0001 (7)
C2C	0.0171 (9)	0.0180 (10)	0.0230 (10)	−0.0005 (8)	−0.0024 (8)	0.0012 (8)
P1	0.0149 (2)	0.0125 (2)	0.0184 (2)	−0.0002 (2)	−0.00181 (17)	−0.00174 (19)
O2B	0.0221 (7)	0.0141 (7)	0.0247 (7)	−0.0016 (5)	−0.0009 (6)	−0.0013 (6)
N2B	0.0176 (8)	0.0166 (8)	0.0211 (8)	0.0007 (6)	−0.0062 (7)	0.0024 (6)
N4B	0.0166 (8)	0.0137 (8)	0.0174 (8)	0.0017 (6)	−0.0024 (6)	0.0021 (6)
N3B	0.0182 (8)	0.0160 (8)	0.0216 (8)	0.0006 (7)	−0.0019 (7)	0.0008 (6)
C2B	0.0171 (9)	0.0157 (9)	0.0169 (9)	0.0012 (7)	0.0027 (8)	0.0018 (7)
C3B	0.0124 (8)	0.0189 (9)	0.0155 (9)	−0.0011 (7)	0.0007 (7)	0.0011 (7)
O3	0.0214 (7)	0.0151 (6)	0.0197 (7)	−0.0021 (5)	−0.0041 (6)	0.0010 (5)
C3A	0.0188 (9)	0.0161 (10)	0.0199 (10)	0.0015 (7)	0.0014 (8)	−0.0001 (7)
O2	0.0193 (7)	0.0136 (6)	0.0412 (9)	0.0006 (5)	0.0063 (6)	0.0013 (6)
O1	0.0266 (8)	0.0177 (8)	0.0519 (10)	0.0006 (6)	−0.0217 (8)	−0.0017 (7)
N3A	0.0194 (8)	0.0145 (8)	0.0215 (8)	0.0002 (6)	0.0006 (7)	−0.0010 (6)
N2A	0.0226 (9)	0.0121 (7)	0.0239 (8)	0.0019 (6)	−0.0006 (7)	0.0013 (6)
O2A	0.0202 (7)	0.0217 (7)	0.0249 (7)	−0.0009 (6)	−0.0033 (6)	−0.0024 (6)
N1A	0.0279 (10)	0.0158 (9)	0.0311 (10)	0.0014 (7)	−0.0072 (8)	0.0009 (7)
C1B	0.0161 (9)	0.0146 (9)	0.0191 (9)	0.0012 (7)	0.0047 (7)	−0.0001 (7)
N4A	0.0184 (9)	0.0107 (8)	0.0232 (8)	0.0004 (6)	−0.0009 (7)	−0.0019 (6)
O1B	0.0181 (7)	0.0147 (6)	0.0194 (7)	−0.0009 (5)	−0.0042 (5)	0.0000 (5)
O4	0.0594 (12)	0.0425 (11)	0.0327 (9)	−0.0305 (9)	0.0219 (9)	−0.0148 (7)
O1A	0.0214 (7)	0.0154 (7)	0.0358 (8)	0.0041 (6)	−0.0132 (7)	−0.0001 (6)
C1A	0.0134 (9)	0.0166 (9)	0.0228 (10)	−0.0001 (7)	0.0003 (8)	−0.0010 (7)
C2A	0.0149 (9)	0.0168 (9)	0.0201 (9)	−0.0003 (7)	0.0020 (7)	−0.0022 (7)

Geometric parameters (Å, º) top

O6—N1	1.247 (2)	N2B—N3B	1.358 (2)
N3C—C2C	1.292 (3)	N2B—H2B	0.86
N3C—N2C	1.368 (2)	N4B—C3B	1.342 (3)
O1C—C1C	1.245 (3)	N4B—C2B	1.362 (3)
N1B—C3B	1.320 (3)	N4B—H4B	0.86
N1B—H5B	0.86	N3B—C2B	1.303 (3)
N1B—H3B	0.86	C2B—C1B	1.482 (3)
N4C—C3C	1.333 (3)	C3A—N1A	1.314 (3)
N4C—C2C	1.365 (3)	C3A—N2A	1.339 (3)
N4C—H4C	0.86	C3A—N4A	1.343 (2)
N1—O7	1.241 (2)	O2—H2	0.82
N1—O5	1.248 (2)	N3A—C2A	1.292 (3)
C3C—N1C	1.311 (3)	N3A—N2A	1.367 (2)
C3C—N2C	1.337 (3)	N2A—H2A	0.86
O2C—C1C	1.238 (3)	O2A—C1A	1.222 (2)
N2C—H2C	0.86	N1A—H5A	0.86
C1C—C2C	1.493 (3)	N1A—H3A	0.86
N1C—H5C	0.86	C1B—O1B	1.290 (2)
N1C—H3C	0.86	N4A—C2A	1.372 (3)
P1—O1	1.5068 (16)	N4A—H4A	0.86
P1—O3	1.5156 (14)	O1B—H1B	0.82
P1—O4	1.5371 (16)	O4—H4	0.82
P1—O2	1.5402 (14)	O1A—C1A	1.266 (2)
O2B—C1B	1.215 (2)	O1A—H1A	0.82
N2B—C3B	1.336 (3)	C1A—C2A	1.494 (3)

C2C—N3C—N2C	104.11 (16)	C3B—N4B—H4B	126.7
C3B—N1B—H5B	120	C2B—N4B—H4B	126.7
C3B—N1B—H3B	120	C2B—N3B—N2B	103.72 (16)
H5B—N1B—H3B	120	N3B—C2B—N4B	111.91 (17)
C3C—N4C—C2C	107.38 (17)	N3B—C2B—C1B	121.13 (17)
C3C—N4C—H4C	126.3	N4B—C2B—C1B	126.94 (17)
C2C—N4C—H4C	126.3	N1B—C3B—N2B	126.42 (18)
O7—N1—O6	120.32 (16)	N1B—C3B—N4B	127.92 (18)
O7—N1—O5	119.72 (16)	N2B—C3B—N4B	105.64 (17)
O6—N1—O5	119.94 (18)	N1A—C3A—N2A	126.59 (19)
N1C—C3C—N4C	128.80 (19)	N1A—C3A—N4A	127.73 (19)
N1C—C3C—N2C	125.70 (18)	N2A—C3A—N4A	105.69 (17)
N4C—C3C—N2C	105.49 (17)	P1—O2—H2	109.5
C3C—N2C—N3C	111.56 (16)	C2A—N3A—N2A	104.42 (16)
C3C—N2C—H2C	124.2	C3A—N2A—N3A	111.50 (16)
N3C—N2C—H2C	124.2	C3A—N2A—H2A	124.3
O2C—C1C—O1C	127.77 (19)	N3A—N2A—H2A	124.3
O2C—C1C—C2C	115.2 (2)	C3A—N1A—H5A	120
O1C—C1C—C2C	117.04 (18)	C3A—N1A—H3A	120
C3C—N1C—H5C	120	H5A—N1A—H3A	120
C3C—N1C—H3C	120	O2B—C1B—O1B	127.51 (19)
H5C—N1C—H3C	120	O2B—C1B—C2B	119.06 (18)
N3C—C2C—N4C	111.43 (17)	O1B—C1B—C2B	113.41 (16)
N3C—C2C—C1C	122.84 (19)	C3A—N4A—C2A	106.82 (16)
N4C—C2C—C1C	125.72 (19)	C3A—N4A—H4A	126.6
O1—P1—O3	113.02 (9)	C2A—N4A—H4A	126.6
O1—P1—O4	107.73 (11)	C1B—O1B—H1B	109.5
O3—P1—O4	111.50 (8)	P1—O4—H4	109.5
O1—P1—O2	108.65 (9)	C1A—O1A—H1A	109.5
O3—P1—O2	107.95 (8)	O2A—C1A—O1A	129.23 (19)
O4—P1—O2	107.83 (10)	O2A—C1A—C2A	116.94 (17)
C3B—N2B—N3B	112.03 (16)	O1A—C1A—C2A	113.83 (17)
C3B—N2B—H2B	124	N3A—C2A—N4A	111.56 (18)
N3B—N2B—H2B	124	N3A—C2A—C1A	123.02 (18)
C3B—N4B—C2B	106.68 (16)	N4A—C2A—C1A	125.42 (17)

C2C—N4C—C3C—N1C	−178.8 (2)	C2B—N4B—C3B—N1B	−179.47 (19)
C2C—N4C—C3C—N2C	1.5 (2)	C2B—N4B—C3B—N2B	−0.86 (19)
N1C—C3C—N2C—N3C	179.1 (2)	N1A—C3A—N2A—N3A	178.89 (19)
N4C—C3C—N2C—N3C	−1.2 (2)	N4A—C3A—N2A—N3A	−0.6 (2)
C2C—N3C—N2C—C3C	0.4 (2)	C2A—N3A—N2A—C3A	−0.1 (2)
N2C—N3C—C2C—N4C	0.6 (2)	N3B—C2B—C1B—O2B	7.5 (3)
N2C—N3C—C2C—C1C	−178.60 (19)	N4B—C2B—C1B—O2B	−174.60 (18)
C3C—N4C—C2C—N3C	−1.3 (2)	N3B—C2B—C1B—O1B	−171.11 (17)
C3C—N4C—C2C—C1C	177.8 (2)	N4B—C2B—C1B—O1B	6.8 (3)
O2C—C1C—C2C—N3C	1.2 (3)	N1A—C3A—N4A—C2A	−178.5 (2)
O1C—C1C—C2C—N3C	−177.4 (2)	N2A—C3A—N4A—C2A	1.0 (2)
O2C—C1C—C2C—N4C	−177.9 (2)	N2A—N3A—C2A—N4A	0.8 (2)
O1C—C1C—C2C—N4C	3.5 (3)	N2A—N3A—C2A—C1A	−178.54 (16)
C3B—N2B—N3B—C2B	−0.7 (2)	C3A—N4A—C2A—N3A	−1.1 (2)
N2B—N3B—C2B—N4B	0.1 (2)	C3A—N4A—C2A—C1A	178.15 (18)
N2B—N3B—C2B—C1B	178.28 (17)	O2A—C1A—C2A—N3A	7.6 (3)
C3B—N4B—C2B—N3B	0.5 (2)	O1A—C1A—C2A—N3A	−172.49 (19)
C3B—N4B—C2B—C1B	−177.57 (19)	O2A—C1A—C2A—N4A	−171.63 (18)
N3B—N2B—C3B—N1B	179.60 (19)	O1A—C1A—C2A—N4A	8.3 (3)
N3B—N2B—C3B—N4B	1.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1B—H5B···O2Cⁱ	0.86	2.15	2.826 (2)	135
N1B—H5B···O1ⁱⁱ	0.86	2.35	2.977 (2)	130
N1B—H3B···O7	0.86	2.24	3.030 (2)	152
N1B—H3B···O1A	0.86	2.54	3.161 (2)	129
N4C—H4C···O5	0.86	1.92	2.765 (2)	169
N4C—H4C···O6	0.86	2.5	3.142 (2)	132
N4C—H4C···N1	0.86	2.55	3.369 (2)	160
N2C—H2C···O2Aⁱⁱⁱ	0.86	2.21	2.876 (2)	135
N2C—H2C···N3Aⁱⁱⁱ	0.86	2.22	2.971 (2)	146
N1C—H5C···O6	0.86	2.28	3.035 (2)	146
N1C—H5C···O1B	0.86	2.5	3.081 (2)	126
N1C—H3C···O2Aⁱⁱⁱ	0.86	2.17	2.888 (2)	140
N1C—H3C···O3	0.86	2.61	3.224 (2)	129
N2B—H2B···O2Cⁱ	0.86	2.03	2.706 (2)	135
N2B—H2B···N3Cⁱ	0.86	2.27	3.004 (2)	144
N4B—H4B···O6	0.86	1.92	2.780 (2)	177
N4B—H4B···O7	0.86	2.66	3.276 (2)	130
N4B—H4B···N1	0.86	2.64	3.444 (2)	157
O2—H2···O1C^iv	0.82	1.77	2.5563 (19)	160
N2A—H2A···O2B^v	0.86	2.17	2.858 (2)	137
N2A—H2A···N3B^v	0.86	2.32	3.071 (2)	146
N1A—H5A···O2B^v	0.86	2.2	2.918 (2)	140
N1A—H5A···O2^v	0.86	2.6	3.244 (2)	133
N1A—H3A···O5	0.86	2.26	3.022 (2)	148
N1A—H3A···O1C	0.86	2.38	2.987 (2)	129
N4A—H4A···O7	0.86	1.93	2.784 (2)	172
N4A—H4A···O5	0.86	2.52	3.157 (2)	132
N4A—H4A···N1	0.86	2.57	3.388 (2)	160
O1B—H1B···O3	0.82	1.65	2.4648 (19)	175
O4—H4···O3^vi	0.82	1.92	2.671 (2)	151
O1A—H1A···O1ⁱⁱ	0.82	1.62	2.423 (2)	166

Symmetry codes: (i) x+1/2, y−1/2, z+1; (ii) x+1/2, y+1/2, z+1; (iii) x−1/2, y−1/2, z−1; (iv) x, y−1, z; (v) x, y+1, z; (vi) x, −y+2, z+1/2.

Experimental details

Crystal data
Chemical formula	2C₃H₅N₄O₂⁺·NO³⁻·H₂PO₄⁻·C₃H₄N₄O₂
M_r	545.32
Crystal system, space group	Monoclinic, Cc
Temperature (K)	180
a, b, c (Å)	19.2249 (13), 13.2036 (7), 7.7468 (5)
β (°)	101.079 (7)
V (Å³)	1929.8 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.45 × 0.43 × 0.16

Data collection
Diffractometer	Agilent Xcalibur Sapphire1 long-nozzle diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.832, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	10050, 3836, 3735
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.067, 1.05
No. of reflections	3836
No. of parameters	330
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.27
Absolute structure	Flack (1983), 1858 Friedel pairs
Absolute structure parameter	0.33 (7)

Computer programs: CrysAlis PRO (Agilent, 2011), SIR2002 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg & Berndt, 2001), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1B—H3B···O7	0.86	2.24	3.030 (2)	152
N4C—H4C···O5	0.86	1.92	2.765 (2)	169
N4B—H4B···O6	0.86	1.92	2.780 (2)	177
O2—H2···O1Cⁱ	0.82	1.77	2.5563 (19)	160
N4A—H4A···O7	0.86	1.93	2.784 (2)	172
O1B—H1B···O3	0.82	1.65	2.4648 (19)	175
O4—H4···O3ⁱⁱ	0.82	1.92	2.671 (2)	151
O1A—H1A···O1ⁱⁱⁱ	0.82	1.62	2.423 (2)	166

Symmetry codes: (i) x, y−1, z; (ii) x, −y+2, z+1/2; (iii) x+1/2, y+1/2, z+1.

Footnotes

‡Département Sciences de la Matière, Faculté des Sciences Exactes et Sciences de la Nature et de la Vie, Université Larbi Ben M'hidi, 04000 Oum El Bouaghi, Algeria.

Acknowledgements

We are grateful to the LCATM Laboratory, Université Larbi Ben M'Hidi, Oum El Bouaghi, Algeria, for financial support.

References

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