2-Amino­pyrimidinium picrate

Narayana, B.; Sarojini, B.K.; Prakash Kamath, K.; Yathirajan, H.S.; Bolte, M.

doi:10.1107/S1600536807062599

organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Pages o117-o118

https://doi.org/10.1107/S1600536807062599

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2-Aminopyrimidinium picrate

B. Narayana,^a B. K. Sarojini,^b K. Prakash Kamath,^c H. S. Yathirajan ^d and Michael Bolte ^e ^*

^aDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, ^bDepartment of Chemistry, P. A. College of Engineering, Nadupadavu, Mangalore 574 153, India, ^cDepartment of Physics, Mangalore University, Mangalagangotri 574 199, India, ^dDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and ^eInstitut für Anorganische Chemie, J. W. Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt/Main, Germany
^*Correspondence e-mail: bolte@chemie.uni-frankfurt.de

(Received 21 November 2007; accepted 23 November 2007; online 6 December 2007)

The geometric parameters of the title compound, C₄H₆N₃⁺·C₆H₂N₃O₇⁻, are in the usual ranges. While two nitro groups are almost coplanar with the aromatic picrate ring [dihedral angles 3.0 (2) and 4.4 (3)°], the third is significantly twisted out of this plane [dihedral angle 46.47 (8)°]. Anions and cations are connected via N—H⋯O hydrogen bonds. The molecules crystallize in planes parallel to (1 $[\overline{2}]$ 1).

Related literature

For related literature, see: Barraclough & Smith (1995 ); Etter et al. (1990 ); Fischer et al. (2007 ); Goswami et al. (2000 ); Gueiffier et al. (1996 ); Katritzky et al. (2003 ); Rival et al. (1991 ); Sanfilippo et al. (1988 ); Scheinbeim & Schempp (1976 ); Schlueter et al. (2006 ); Tully et al. (1991 ); Yathirajan, Bindya et al. (2007a ,b ); Yathirajan, Mayekar et al. (2007 ); Yathirajan, Narayana et al. (2007 ).

Experimental

Crystal data

C₄H₆N₃⁺·C₆H₂N₃O₇⁻
M_r = 324.22
Triclinic, $[P \overline 1]$
a = 5.8803 (7) Å
b = 8.0025 (10) Å
c = 13.8108 (17) Å
α = 88.021 (10)°
β = 82.322 (9)°
γ = 88.739 (10)°
V = 643.59 (14) Å³
Z = 2
Mo Kα radiation
μ = 0.14 mm⁻¹
T = 173 (2) K
0.26 × 0.22 × 0.09 mm

Data collection

Stoe IPDSII two-circle diffractometer
Absorption correction: none
8757 measured reflections
2402 independent reflections
1927 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.099
S = 1.01
2402 reflections
220 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N6ⁱ	0.87 (2)	2.09 (2)	2.958 (2)	177.0 (18)
N1—H1B⋯O11	0.91 (2)	1.97 (2)	2.7577 (19)	143.7 (18)
N1—H1B⋯O17	0.91 (2)	2.50 (2)	3.2488 (18)	140.0 (17)
N2—H2⋯O11	0.90 (2)	1.84 (2)	2.6501 (16)	148.6 (19)
N2—H2⋯O12	0.90 (2)	2.31 (2)	2.9792 (18)	131.6 (17)
Symmetry code: (i) -x+2, -y+1, -z.

Data collection: X-AREA (Stoe & Cie, 2001 ); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536807062599/at2509sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807062599/at2509Isup2.hkl

checkCIF report

Comment top

Pyrimidine is a heterocyclic aromatic organic compound similar to benzene and pyridine, containing two nitrogen atoms at positions 1 and 3 of the six-member ring. A pyrimidine has many properties in common with pyridine, as the number of nitrogen atoms in the ring increases the ring π-electrons become less energetic and electrophilic aromatic substitution gets more difficult while nucleophilic aromatic substitution gets easier. Pyrimidines are important compounds in pharmaceutical chemistry as antiviral agents (Gueiffier et al., 1996), inotropic and β-blocking agents (Barraclough & Smith, 1995), antifungal agents (Rival et al. 1991), benzodiazepine receptor agonists (Tully et al.1991), and calcium channel blockers (Sanfilippo et al., 1988). The synthesis of imidazo[1,2-a]pyrimidines has been widely investigated and one of the most common strategies uses 2-aminopyrimidine as the starting material (Katritzky et al., 2003). The crystal structures of the following compounds have been previously reported, viz; 2-aminopyrimidine (Scheinbeim & Schempp, 1976), 1:1 hetero-assembly of 2-aminopyrimidine and (+)-camphoric acid (Goswami, et al., 2000), 2-aminopyrimidine-succinic acid (1:1) cocrystal (Etter et al., 1990), 5-aminopyrimidine (Schlueter et al., 2006), 5-bromopyrimidin-2(1H)-one (Yathirajan, Narayana, Ashalatha et al., 2007), ethyl 7-methyl-2-[4-(methylsulfanyl)benzylidene]-5-[4-(methylsulfanyl)phenyl]-3-oxo-2, 3-dihydro-5H-thiazolo[3,2-a]pyrimidine-6-carboxylate (Fischer et al., 2007), 2-(4-methylbenzoyloxymethyl)-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1 -yl)tetrahydrofuran-3-yl 4-methylbenzoate (Yathirajan, Mayekar, Sarojini et al., 2007), methyl (4-oxo-1-phenyl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-5-yl)acetate (Yathirajan, Bindya, Sarojini et al., 2007a), ethyl (4-oxo-1-phenyl-1,4-dihydro-5H-pyrazolo[3,4-d]pyrimidin-5-yl)acetate (Yathirajan, Bindya, Sarojini et al., 2007b). In continuation to our work on picrates of biologically important molecules, we have prepared a new picrate of 2-aminopyrimidine, and its crystal structure is reported.

Geometric parameters of the title compound are in the usual ranges. Whereas two nitrogroups are almost coplanar with the aromatic picrate ring [dihedral angles 3.0 (2)° and 4.4 (3)°] the third one is significantly twisted [dihedral angle 46.47 (8)°] out of this plane Anions and cations are connected via N—H···O hydrogen bonds. The molecules crystallize in planes parallel to (1 - 2 1).

Related literature top

For related literature, see: Barraclough & Smith (1995); Etter et al. (1990); Fischer et al. (2007); Goswami et al. (2000); Gueiffier et al. (1996); Katritzky et al. (2003); Rival et al. (1991); Sanfilippo et al. (1988); Scheinbeim & Schempp (1976); Schlueter et al. (2006); Tully et al. (1991); Yathirajan, Bindya et al. (2007a,b); Yathirajan, Mayekar et al. (2007); Yathirajan, Narayana et al. (2007).

Experimental top

2-Aminopyrimidine (0.95 g, 0.01 mol) was dissolved in 20 ml of ethanol. Picric acid (2.29 g, 0.01 mol) was dissolved in 10 ml of water. Both the solutions were mixed and to this, 5 ml of 5 M HCl was added and stirred for few minutes. The formed complex was filtered, dried and recrystallized from ethanol (m.p.: 413–415 K). Composition: Found (calculated): C 37.01(37.05), H 2.46(2.49), N 25.87% (25.92%).

Structure description top

For related literature, see: Barraclough & Smith (1995); Etter et al. (1990); Fischer et al. (2007); Goswami et al. (2000); Gueiffier et al. (1996); Katritzky et al. (2003); Rival et al. (1991); Sanfilippo et al. (1988); Scheinbeim & Schempp (1976); Schlueter et al. (2006); Tully et al. (1991); Yathirajan, Bindya et al. (2007a,b); Yathirajan, Mayekar et al. (2007); Yathirajan, Narayana et al. (2007).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top

Fig. 1. Perspective view of the title compound with the atom numbering; displacement ellipsoids are at the 50% probability level. The hydrogen bonds are shown as dashed lines.

2-Aminopyrimidinium picrate top

Crystal data top

C₄H₆N₃⁺·C₆H₂N₃O₇⁻	Z = 2
M_r = 324.22	F(000) = 332
Triclinic, P1	D_x = 1.673 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.8803 (7) Å	Cell parameters from 8213 reflections
b = 8.0025 (10) Å	θ = 3.5–25.8°
c = 13.8108 (17) Å	µ = 0.15 mm⁻¹
α = 88.021 (10)°	T = 173 K
β = 82.322 (9)°	Plate, yellow
γ = 88.739 (10)°	0.26 × 0.22 × 0.09 mm
V = 643.59 (14) Å³

Data collection top

Stoe IPDSII two-circle diffractometer	1927 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.042
Graphite monochromator	θ_max = 25.6°, θ_min = 3.5°
ω scans	h = −7→7
8757 measured reflections	k = −9→9
2402 independent reflections	l = −16→16

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0661P)²] where P = (F_o² + 2F_c²)/3
2402 reflections	(Δ/σ)_max < 0.001
220 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₄H₆N₃⁺·C₆H₂N₃O₇⁻	γ = 88.739 (10)°
M_r = 324.22	V = 643.59 (14) Å³
Triclinic, P1	Z = 2
a = 5.8803 (7) Å	Mo Kα radiation
b = 8.0025 (10) Å	µ = 0.15 mm⁻¹
c = 13.8108 (17) Å	T = 173 K
α = 88.021 (10)°	0.26 × 0.22 × 0.09 mm
β = 82.322 (9)°

Data collection top

Stoe IPDSII two-circle diffractometer	1927 reflections with I > 2σ(I)
8757 measured reflections	R_int = 0.042
2402 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.20 e Å⁻³
2402 reflections	Δρ_min = −0.27 e Å⁻³
220 parameters

Special details top

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
N1	0.7277 (3)	0.40774 (18)	0.07873 (11)	0.0279 (3)
H1A	0.799 (3)	0.422 (2)	0.0195 (16)	0.033 (5)*
H1B	0.600 (4)	0.346 (3)	0.0984 (15)	0.039 (5)*
C1	0.8282 (3)	0.47463 (18)	0.14768 (11)	0.0199 (3)
N2	0.7333 (2)	0.45943 (15)	0.24319 (9)	0.0206 (3)
H2	0.604 (4)	0.400 (3)	0.2556 (15)	0.039 (5)*
C3	0.8321 (3)	0.52828 (18)	0.31540 (11)	0.0229 (3)
H3	0.7618	0.5183	0.3814	0.027*
C4	1.0334 (3)	0.61214 (19)	0.29261 (11)	0.0241 (3)
H4	1.1076	0.6609	0.3415	0.029*
C5	1.1247 (3)	0.62249 (18)	0.19338 (12)	0.0229 (3)
H5	1.2654	0.6791	0.1762	0.027*
N6	1.0274 (2)	0.55855 (15)	0.12224 (9)	0.0228 (3)
C11	0.2209 (2)	0.17922 (17)	0.24085 (11)	0.0194 (3)
C12	0.0995 (2)	0.17467 (18)	0.33896 (11)	0.0196 (3)
C13	−0.1064 (2)	0.09207 (18)	0.36532 (11)	0.0201 (3)
H13	−0.1809	0.0931	0.4307	0.024*
C14	−0.2010 (2)	0.00844 (17)	0.29461 (11)	0.0197 (3)
C15	−0.0957 (3)	0.00409 (18)	0.19783 (11)	0.0209 (3)
H15	−0.1612	−0.0560	0.1506	0.025*
C16	0.1043 (2)	0.08881 (18)	0.17311 (11)	0.0197 (3)
N11	0.1908 (2)	0.26127 (16)	0.41664 (10)	0.0238 (3)
N12	−0.4142 (2)	−0.08122 (16)	0.32163 (10)	0.0250 (3)
N13	0.2118 (2)	0.08312 (16)	0.07100 (9)	0.0226 (3)
O11	0.41007 (18)	0.24842 (14)	0.21384 (8)	0.0276 (3)
O12	0.3751 (2)	0.33240 (17)	0.39985 (9)	0.0371 (3)
O13	0.0778 (2)	0.2607 (2)	0.49744 (9)	0.0534 (4)
O14	−0.5137 (2)	−0.07121 (17)	0.40512 (9)	0.0396 (3)
O15	−0.4859 (2)	−0.16322 (15)	0.25825 (10)	0.0366 (3)
O16	0.2234 (2)	−0.05385 (14)	0.03198 (9)	0.0323 (3)
O17	0.2799 (2)	0.21390 (15)	0.02874 (9)	0.0334 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0296 (8)	0.0360 (8)	0.0185 (7)	−0.0172 (6)	−0.0015 (6)	−0.0027 (6)
C1	0.0220 (7)	0.0191 (7)	0.0183 (7)	−0.0042 (5)	−0.0013 (6)	−0.0009 (6)
N2	0.0207 (6)	0.0211 (6)	0.0201 (7)	−0.0059 (5)	−0.0014 (5)	−0.0018 (5)
C3	0.0273 (8)	0.0228 (7)	0.0186 (8)	−0.0021 (6)	−0.0026 (6)	−0.0037 (6)
C4	0.0275 (8)	0.0234 (7)	0.0227 (8)	−0.0042 (6)	−0.0063 (6)	−0.0054 (6)
C5	0.0226 (7)	0.0211 (7)	0.0254 (8)	−0.0073 (6)	−0.0034 (6)	−0.0035 (6)
N6	0.0244 (7)	0.0235 (6)	0.0206 (7)	−0.0087 (5)	−0.0015 (5)	−0.0031 (5)
C11	0.0190 (7)	0.0181 (7)	0.0215 (8)	−0.0028 (5)	−0.0030 (6)	−0.0020 (6)
C12	0.0205 (7)	0.0205 (7)	0.0187 (8)	−0.0034 (6)	−0.0049 (6)	−0.0030 (6)
C13	0.0200 (7)	0.0199 (7)	0.0199 (8)	−0.0011 (5)	−0.0007 (6)	0.0001 (6)
C14	0.0158 (7)	0.0179 (7)	0.0255 (8)	−0.0042 (5)	−0.0022 (6)	−0.0012 (6)
C15	0.0221 (7)	0.0193 (7)	0.0226 (8)	−0.0019 (5)	−0.0063 (6)	−0.0048 (6)
C16	0.0208 (7)	0.0208 (7)	0.0176 (8)	−0.0014 (6)	−0.0025 (6)	−0.0018 (6)
N11	0.0244 (7)	0.0276 (7)	0.0196 (7)	−0.0063 (5)	−0.0023 (5)	−0.0039 (5)
N12	0.0193 (6)	0.0241 (6)	0.0316 (8)	−0.0048 (5)	−0.0031 (5)	−0.0008 (6)
N13	0.0212 (6)	0.0270 (7)	0.0201 (7)	−0.0026 (5)	−0.0035 (5)	−0.0052 (5)
O11	0.0226 (6)	0.0368 (6)	0.0233 (6)	−0.0141 (5)	0.0006 (4)	−0.0050 (5)
O12	0.0342 (7)	0.0518 (8)	0.0267 (6)	−0.0260 (6)	−0.0030 (5)	−0.0070 (5)
O13	0.0449 (8)	0.0925 (12)	0.0221 (7)	−0.0335 (7)	0.0095 (6)	−0.0245 (7)
O14	0.0298 (7)	0.0545 (8)	0.0322 (7)	−0.0175 (6)	0.0075 (5)	−0.0038 (6)
O15	0.0306 (6)	0.0386 (7)	0.0425 (8)	−0.0170 (5)	−0.0067 (5)	−0.0107 (6)
O16	0.0375 (7)	0.0321 (6)	0.0272 (6)	−0.0035 (5)	−0.0006 (5)	−0.0137 (5)
O17	0.0422 (7)	0.0339 (6)	0.0227 (6)	−0.0089 (5)	0.0017 (5)	0.0014 (5)

Geometric parameters (Å, º) top

N1—C1	1.320 (2)	C12—C13	1.392 (2)
N1—H1A	0.87 (2)	C12—N11	1.4631 (19)
N1—H1B	0.91 (2)	C13—C14	1.385 (2)
C1—N6	1.3622 (19)	C13—H13	0.9500
C1—N2	1.3643 (19)	C14—C15	1.397 (2)
N2—C3	1.3572 (19)	C14—N12	1.4568 (18)
N2—H2	0.90 (2)	C15—C16	1.368 (2)
C3—C4	1.368 (2)	C15—H15	0.9500
C3—H3	0.9500	C16—N13	1.4682 (19)
C4—C5	1.404 (2)	N11—O13	1.2202 (18)
C4—H4	0.9500	N11—O12	1.2262 (17)
C5—N6	1.324 (2)	N12—O14	1.2258 (18)
C5—H5	0.9500	N12—O15	1.2349 (17)
C11—O11	1.2588 (18)	N13—O17	1.2289 (17)
C11—C12	1.444 (2)	N13—O16	1.2345 (17)
C11—C16	1.452 (2)

C1—N1—H1A	115.1 (13)	C13—C12—N11	116.45 (13)
C1—N1—H1B	117.1 (13)	C11—C12—N11	120.10 (12)
H1A—N1—H1B	127.5 (19)	C14—C13—C12	118.89 (14)
N1—C1—N6	119.19 (14)	C14—C13—H13	120.6
N1—C1—N2	120.24 (13)	C12—C13—H13	120.6
N6—C1—N2	120.57 (13)	C13—C14—C15	122.04 (13)
C3—N2—C1	121.42 (13)	C13—C14—N12	119.44 (14)
C3—N2—H2	122.1 (13)	C15—C14—N12	118.50 (13)
C1—N2—H2	116.5 (13)	C16—C15—C14	118.09 (13)
N2—C3—C4	119.58 (14)	C16—C15—H15	121.0
N2—C3—H3	120.2	C14—C15—H15	121.0
C4—C3—H3	120.2	C15—C16—C11	124.88 (14)
C3—C4—C5	116.62 (14)	C15—C16—N13	117.24 (13)
C3—C4—H4	121.7	C11—C16—N13	117.85 (12)
C5—C4—H4	121.7	O13—N11—O12	121.68 (13)
N6—C5—C4	124.25 (14)	O13—N11—C12	118.02 (12)
N6—C5—H5	117.9	O12—N11—C12	120.30 (13)
C4—C5—H5	117.9	O14—N12—O15	123.36 (13)
C5—N6—C1	117.53 (13)	O14—N12—C14	118.93 (13)
O11—C11—C12	125.89 (13)	O15—N12—C14	117.70 (13)
O11—C11—C16	121.46 (13)	O17—N13—O16	123.85 (13)
C12—C11—C16	112.63 (13)	O17—N13—C16	118.75 (12)
C13—C12—C11	123.45 (13)	O16—N13—C16	117.38 (12)

N1—C1—N2—C3	−179.40 (14)	C14—C15—C16—C11	2.1 (2)
N6—C1—N2—C3	0.7 (2)	C14—C15—C16—N13	−179.82 (13)
C1—N2—C3—C4	−1.3 (2)	O11—C11—C16—C15	176.85 (14)
N2—C3—C4—C5	0.6 (2)	C12—C11—C16—C15	−1.5 (2)
C3—C4—C5—N6	0.7 (2)	O11—C11—C16—N13	−1.2 (2)
C4—C5—N6—C1	−1.3 (2)	C12—C11—C16—N13	−179.53 (12)
N1—C1—N6—C5	−179.32 (15)	C13—C12—N11—O13	−2.7 (2)
N2—C1—N6—C5	0.6 (2)	C11—C12—N11—O13	176.73 (15)
O11—C11—C12—C13	−178.11 (14)	C13—C12—N11—O12	177.68 (14)
C16—C11—C12—C13	0.2 (2)	C11—C12—N11—O12	−2.9 (2)
O11—C11—C12—N11	2.5 (2)	C13—C14—N12—O14	4.9 (2)
C16—C11—C12—N11	−179.19 (12)	C15—C14—N12—O14	−176.38 (14)
C11—C12—C13—C14	0.4 (2)	C13—C14—N12—O15	−175.46 (14)
N11—C12—C13—C14	179.81 (13)	C15—C14—N12—O15	3.2 (2)
C12—C13—C14—C15	0.2 (2)	C15—C16—N13—O17	133.79 (15)
C12—C13—C14—N12	178.82 (13)	C11—C16—N13—O17	−48.03 (19)
C13—C14—C15—C16	−1.4 (2)	C15—C16—N13—O16	−44.61 (19)
N12—C14—C15—C16	179.93 (13)	C11—C16—N13—O16	133.57 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N6ⁱ	0.87 (2)	2.09 (2)	2.958 (2)	177.0 (18)
N1—H1B···O11	0.91 (2)	1.97 (2)	2.7577 (19)	143.7 (18)
N1—H1B···O17	0.91 (2)	2.50 (2)	3.2488 (18)	140.0 (17)
N2—H2···O11	0.90 (2)	1.84 (2)	2.6501 (16)	148.6 (19)
N2—H2···O12	0.90 (2)	2.31 (2)	2.9792 (18)	131.6 (17)

Symmetry code: (i) −x+2, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₄H₆N₃⁺·C₆H₂N₃O₇⁻
M_r	324.22
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	5.8803 (7), 8.0025 (10), 13.8108 (17)
α, β, γ (°)	88.021 (10), 82.322 (9), 88.739 (10)
V (Å³)	643.59 (14)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.15
Crystal size (mm)	0.26 × 0.22 × 0.09

Data collection
Diffractometer	Stoe IPDSII two-circle
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8757, 2402, 1927
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.608

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.099, 1.01
No. of reflections	2402
No. of parameters	220
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.27

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N6ⁱ	0.87 (2)	2.09 (2)	2.958 (2)	177.0 (18)
N1—H1B···O11	0.91 (2)	1.97 (2)	2.7577 (19)	143.7 (18)
N1—H1B···O17	0.91 (2)	2.50 (2)	3.2488 (18)	140.0 (17)
N2—H2···O11	0.90 (2)	1.84 (2)	2.6501 (16)	148.6 (19)
N2—H2···O12	0.90 (2)	2.31 (2)	2.9792 (18)	131.6 (17)

Symmetry code: (i) −x+2, −y+1, −z.

Acknowledgements

BN thanks Mangalore University for the use of research facilities.

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