Cytosinium–hydrogen maleate–cytosine (1/1/1)

Benali-Cherif, N.; Falek, W.; Direm, A.

doi:10.1107/S1600536809046571

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Pages o3058-o3059

doi:10.1107/S1600536809046571

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Cytosinium–hydrogen maleate–cytosine (1/1/1)

Nourredine Benali-Cherif,^a ^* Wahiba Falek ^b and Amani Direm ^a

^aLaboratoire des Structures, Propriétés et Interactions Inter-Atomiques, Centre Universitaire Abbes Laghrour, Khenchela 40000, Algeria, and ^bDépartement de Chimie, Université Elhadj Lakhdar, Batna 05000, Algeria
^*Correspondence e-mail: benalicherif@hotmail.com

(Received 1 November 2009; accepted 4 November 2009; online 11 November 2009)

The title organic salt, C₄H₆N₃O⁺·C₄H₃O₄⁻·C₄H₅N₃O, was synthesized from cytosine base and maleic acid. An intramolecular O—H⋯O hydrogen bond occurs in the hydrogen maleate anion. The crystal packing is stabilized by intermolecular N—H⋯O, N—H⋯N and C—H⋯O hydrogen bonds, giving rise to a nearly planar two-dimensional network parallel to (101).

Related literature

For background to cytosine, see: Devlin (1986 ); Johnson & Coghill (1925 ); Mahan et al. (2004 ). For the structure of cytosine, see: Barker & Marsh (1964 ) and for that of cytosine monohydrate, see: Jeffrey & Kinoshita (1963 ); Swamy et al. (2001 ). For the stuctures of inorganic cytosinium salts, see: Mandel (1977 ); Cherouana et al. (2003 ); Jaskólski (1989 ); Bagieu-Beucher (1990 ) and for those of cytosinium salts of organic acids, see: Gdaniec et al. (1989 ); Smith et al. (2005 ); Balasubramanian et al. (1996 ). For the hydrogen maleate anion, see: Madsen & Larsen (1998 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₄H₆N₃O⁺·C₄H₃O₄⁻·C₄H₅N₃O
M_r = 338.29
Monoclinic, C 2/c
a = 27.3226 (5) Å
b = 7.3618 (2) Å
c = 14.6742 (4) Å
β = 93.905 (1)°
V = 2944.77 (13) Å³
Z = 8
Mo Kα radiation
μ = 0.13 mm⁻¹
T = 298 K
0.3 × 0.15 × 0.1 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: none
3490 measured reflections
3485 independent reflections
2603 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.136
S = 1.07
3485 reflections
202 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H1A⋯O4	0.86	1.89	2.7426 (19)	174
N1B—H1B⋯O2ⁱ	0.86	1.91	2.7701 (19)	174
N8A—H8A1⋯O7B	0.86	2.00	2.8582 (19)	178
N8A—H8A2⋯O7Aⁱⁱ	0.86	2.04	2.8329 (19)	153
N3B—H3B⋯N3A	0.86	1.98	2.8370 (19)	176
N8B—H8B1⋯O7A	0.86	1.99	2.8458 (19)	173
N8B—H8B2⋯O7Bⁱⁱⁱ	0.86	2.06	2.8491 (18)	153
O3—H3⋯O1	1.17 (2)	1.25 (2)	2.4167 (16)	173 (2)
C6B—H6B⋯O1ⁱ	0.93	2.50	3.186 (2)	131
C5B—H5B⋯O2^iv	0.93	2.42	3.330 (2)	165
C5A—H5A⋯O4ⁱⁱ	0.93	2.37	3.296 (2)	175
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) x, y+1, z; (iii) x, y-1, z; (iv) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: KappaCCD Server Software (Nonius, 1998 ); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809046571/dn2509sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809046571/dn2509Isup2.hkl

checkCIF report

Comment top

The pyrimidine base, Cytosine, leads to the nucleoside cytidine and its corresponding nucleotide: cytidine 5'-monophosphate. It may be found in very small quantities as a post-modified form, 5-methylcytosine, in certain nucleic acids (Devlin, 1986) such as in tuberculinic acid (Johnson & Coghill, 1925). More recently, 5-fluoro-cytosine (5-FC) has been used as a prodrug in suicide gene therapy of cancer with the crystal structure of bacterial cytosine deaminase (bCD) (Mahan et al., 2004).

The crystal structures of cytosine (Barker & Marsh, 1964) and cytosine monohydrate (Jeffrey & Kinoshita, 1963) were determined many years ago. (Swamy et al., 2001)]. Many inorganic cytosinium salts have been previously synthesized: chloride (Mandel, 1977), nitrate (Cherouana et al., 2003) and dihydrogenphosphate (Jaskólski, 1989; Bagieu-Beucher, 1990). Cytosinium salts of organic acids are also common, the structures of a number of these including trichloroacetate (Gdaniec et al., 1989), Cytosinium 3,5-dinitrosalicylate (Smith, et al., 2005) and hydrogen maleate (Balasubramanian et al., 1996) have been recently reported.

We report here the molecular structure of a novel compound (I) formed from the reaction of cytosine with maleic acid, namely cytosine cytosinium hydrogen maleate. It was prepared in order to extend our study on D—H···A hydrogen bonding in organic systems.

The asymmetric unit in (I) contains a hydrogen maleate anion, a cytosinium cation and a cytosine molecule which are held together by N—H···O and N—H···N hydrogen bonds (Fig. 1; Table 1). As observed in other hydrogen maleate anion, the H atom is roughly in between O1 and O3 (Madsen & Larsen, 1998).

In the crystal packing (Fig.2), cytosine bases and cytosinium cations are linked by N8A–H1N···O7A and N8B–H3N···O7B hydrogen-bonds forming a C(6)R²₂(8) graph-set motif and yielding infinite chains running parallel to the b axis. These chains are connected through N–H···O and C–H···O hydrogen bonds involving the O2 and O4 atoms of the maleate thus generating R²₃(10) and R²₂(7) graph-set motifs (Bernstein et al., 1995) and giving rise to a planar two-dimensionnal network parallel to the (1 0 1) plane (Table 1, Fig. 2).

Related literature top

For background to the pyrimidine base, cytosine, see: Devlin (1986); Johnson & Coghill (1925); Mahan et al. (2004). For the structure of cytosine, see: Barker & Marsh (1964) and for that of cytosine monohydrate, see: Jeffrey & Kinoshita (1963); Swamy et al. (2001). For the stuctures of inorganic cytosinium salts, see: Mandel (1977); Cherouana et al. (2003); Jaskólski (1989); Bagieu-Beucher (1990) and for those of cytosinium salts of organic acids, see: Gdaniec et al. (1989); Smith et al. (2005); Balasubramanian et al. (1996). For the hydrogen maleate anion, see: Madsen & Larsen (1998). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

The title compound was prepared by the reaction between cytosine and maleic acid. A colorless prismatic single-cristals were grown after few days of evaporation at room temperature.

Computing details top

Data collection: KappaCCD Server Software (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. ORTEP view of 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 the formation of the two dimensionnal network through N-H···O, N-H···N and C-H···O hydrogen bonds. H atoms not involved in hydrogen bondings have been omitted for clarity. Hydrogen bonds are shown as dashed lines. [Symmetry codes: (i) x+1/2, -y+3/2, z-1/2; (ii) x, y+1, z; (iii) x, y-1, z; (iv) x+1/2, -y+1/2, z-1/2]

cytosinium–hydrogen maleate–cytosine (1/1/1) top

Crystal data top

C₄H₆N₃O⁺·C₄H₃O₄⁻·C₄H₅N₃O	F(000) = 1408
M_r = 338.29	D_x = 1.526 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 27.3226 (5) Å	Cell parameters from 3490 reflections
b = 7.3618 (2) Å	θ = 2.8–28.0°
c = 14.6742 (4) Å	µ = 0.13 mm⁻¹
β = 93.905 (1)°	T = 298 K
V = 2944.77 (13) Å³	Prism, colourless
Z = 8	0.3 × 0.15 × 0.1 mm

Data collection top

Nonius KappaCCD diffractometer	2603 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.043
Graphite monochromator	θ_max = 28.0°, θ_min = 2.8°
ω–θ scans	h = 0→35
3490 measured reflections	k = 0→9
3485 independent reflections	l = −19→19

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.136	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0596P)² + 1.9669P] where P = (F_o² + 2F_c²)/3
3485 reflections	(Δ/σ)_max < 0.001
202 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₄H₆N₃O⁺·C₄H₃O₄⁻·C₄H₅N₃O	V = 2944.77 (13) Å³
M_r = 338.29	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 27.3226 (5) Å	µ = 0.13 mm⁻¹
b = 7.3618 (2) Å	T = 298 K
c = 14.6742 (4) Å	0.3 × 0.15 × 0.1 mm
β = 93.905 (1)°

Data collection top

Nonius KappaCCD diffractometer	2603 reflections with I > 2σ(I)
3490 measured reflections	R_int = 0.043
3485 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.136	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.36 e Å⁻³
3485 reflections	Δρ_min = −0.23 e Å⁻³
202 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
O7B	0.33929 (4)	1.06422 (15)	0.29275 (9)	0.0427 (3)
N1B	0.40074 (5)	0.90020 (18)	0.23748 (9)	0.0387 (3)
H1B	0.4147	0.9976	0.2199	0.046*
N3B	0.33603 (5)	0.75680 (17)	0.30317 (10)	0.0356 (3)
H3B	0.3085	0.7616	0.3281	0.043*
N8B	0.33306 (6)	0.44790 (19)	0.31458 (11)	0.0497 (4)
H8B1	0.3055	0.4591	0.3390	0.060*
H8B2	0.3452	0.3417	0.3067	0.060*
C2B	0.35779 (6)	0.9147 (2)	0.27857 (11)	0.0345 (3)
C4B	0.35667 (6)	0.5930 (2)	0.28930 (11)	0.0377 (4)
C5B	0.40201 (6)	0.5833 (2)	0.24822 (12)	0.0428 (4)
H5B	0.4171	0.4722	0.2390	0.051*
C6B	0.42225 (6)	0.7386 (2)	0.22325 (12)	0.0429 (4)
H6B	0.4518	0.7356	0.1954	0.052*
O7A	0.23768 (4)	0.47389 (15)	0.38025 (9)	0.0467 (3)
N1A	0.17582 (5)	0.63603 (19)	0.43517 (10)	0.0406 (3)
H1A	0.1605	0.5378	0.4474	0.049*
N3A	0.24320 (5)	0.78198 (17)	0.37790 (10)	0.0366 (3)
N8A	0.24807 (6)	1.09115 (19)	0.37624 (12)	0.0508 (4)
H8A1	0.2757	1.0810	0.3519	0.061*
H8A2	0.2365	1.1970	0.3873	0.061*
C2A	0.21960 (6)	0.6237 (2)	0.39693 (11)	0.0355 (3)
C4A	0.22347 (6)	0.9448 (2)	0.39665 (12)	0.0378 (4)
C5A	0.17782 (6)	0.9546 (2)	0.43695 (13)	0.0429 (4)
H5A	0.1640	1.0659	0.4506	0.051*
C6A	0.15542 (6)	0.7983 (2)	0.45467 (13)	0.0433 (4)
H6A	0.1254	0.8008	0.4808	0.052*
O1	0.00023 (4)	0.51357 (17)	0.62970 (9)	0.0448 (3)
O2	−0.05080 (5)	0.30095 (18)	0.67256 (10)	0.0541 (4)
O3	0.07419 (4)	0.53110 (16)	0.54870 (8)	0.0419 (3)
H3	0.0374 (7)	0.532 (3)	0.5856 (13)	0.063*
O4	0.12212 (5)	0.33885 (18)	0.48081 (9)	0.054
C1	0.08607 (6)	0.3706 (2)	0.52447 (11)	0.038
C2	0.05603 (7)	0.2114 (2)	0.54876 (14)	0.049
H1	0.0676	0.1001	0.5293	0.059*
C3	0.01551 (7)	0.2018 (2)	0.59356 (14)	0.0504 (5)
H2	0.0033	0.0850	0.6003	0.061*
C4	−0.01358 (6)	0.3478 (2)	0.63484 (12)	0.0402 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O7B	0.0443 (6)	0.0235 (6)	0.0615 (8)	0.0016 (4)	0.0113 (5)	−0.0015 (5)
N1B	0.0405 (7)	0.0322 (7)	0.0444 (8)	−0.0021 (5)	0.0104 (6)	−0.0013 (6)
N3B	0.0351 (7)	0.0245 (6)	0.0479 (8)	0.0008 (5)	0.0077 (6)	−0.0014 (5)
N8B	0.0544 (9)	0.0260 (7)	0.0704 (10)	0.0031 (6)	0.0172 (8)	0.0006 (7)
C2B	0.0369 (8)	0.0278 (8)	0.0385 (8)	0.0007 (6)	0.0013 (6)	−0.0017 (6)
C4B	0.0442 (9)	0.0267 (8)	0.0419 (9)	0.0022 (6)	0.0008 (7)	−0.0022 (6)
C5B	0.0440 (9)	0.0352 (9)	0.0500 (10)	0.0104 (7)	0.0084 (8)	−0.0028 (7)
C6B	0.0408 (9)	0.0430 (10)	0.0461 (9)	0.0061 (7)	0.0104 (7)	−0.0036 (7)
O7A	0.0452 (7)	0.0239 (6)	0.0724 (8)	0.0005 (5)	0.0135 (6)	−0.0010 (6)
N1A	0.0380 (7)	0.0313 (7)	0.0533 (8)	−0.0045 (6)	0.0099 (6)	−0.0021 (6)
N3A	0.0374 (7)	0.0215 (6)	0.0514 (8)	0.0010 (5)	0.0061 (6)	0.0001 (6)
N8A	0.0503 (8)	0.0243 (7)	0.0793 (11)	0.0016 (6)	0.0165 (8)	−0.0002 (7)
C2A	0.0361 (8)	0.0259 (8)	0.0446 (9)	0.0003 (6)	0.0029 (7)	−0.0001 (6)
C4A	0.0392 (8)	0.0277 (8)	0.0465 (9)	0.0027 (6)	0.0016 (7)	−0.0014 (7)
C5A	0.0415 (9)	0.0325 (8)	0.0550 (10)	0.0077 (7)	0.0059 (7)	−0.0060 (7)
C6A	0.0362 (8)	0.0433 (10)	0.0510 (10)	0.0031 (7)	0.0082 (7)	−0.0062 (8)
O1	0.0403 (6)	0.0392 (7)	0.0566 (7)	−0.0014 (5)	0.0154 (5)	−0.0037 (6)
O2	0.0455 (7)	0.0501 (8)	0.0694 (9)	−0.0055 (6)	0.0239 (6)	0.0023 (7)
O3	0.0418 (6)	0.0349 (6)	0.0506 (7)	−0.0033 (5)	0.0137 (5)	−0.0028 (5)
O4	0.052	0.046	0.067	0.000	0.030	−0.006
C1	0.037	0.038	0.040	−0.001	0.007	0.000
C2	0.053	0.031	0.067	0.002	0.020	−0.002
C3	0.0526 (10)	0.0309 (9)	0.0696 (12)	−0.0038 (7)	0.0179 (9)	0.0020 (8)
C4	0.0367 (8)	0.0401 (9)	0.0443 (9)	−0.0023 (7)	0.0067 (7)	0.0016 (7)

Geometric parameters (Å, º) top

O7B—C2B	1.2348 (19)	N3A—C2A	1.3697 (19)
N1B—C6B	1.350 (2)	N8A—C4A	1.315 (2)
N1B—C2B	1.360 (2)	N8A—H8A1	0.8600
N1B—H1B	0.8600	N8A—H8A2	0.8600
N3B—C4B	1.353 (2)	C4A—C5A	1.418 (2)
N3B—C2B	1.365 (2)	C5A—C6A	1.337 (2)
N3B—H3B	0.8600	C5A—H5A	0.9300
N8B—C4B	1.314 (2)	C6A—H6A	0.9300
N8B—H8B1	0.8600	O1—C4	1.281 (2)
N8B—H8B2	0.8600	O1—H3	1.25 (2)
C4B—C5B	1.416 (2)	O2—C4	1.239 (2)
C5B—C6B	1.332 (2)	O3—C1	1.282 (2)
C5B—H5B	0.9300	O3—H3	1.17 (2)
C6B—H6B	0.9300	O4—C1	1.2333 (19)
O7A—C2A	1.2398 (19)	C1—C2	1.488 (2)
N1A—C6A	1.357 (2)	C2—C3	1.327 (3)
N1A—C2A	1.358 (2)	C2—H1	0.9300
N1A—H1A	0.8600	C3—C4	1.490 (3)
N3A—C4A	1.3503 (19)	C3—H2	0.9300

C6B—N1B—C2B	122.40 (14)	H8A1—N8A—H8A2	120.0
C6B—N1B—H1B	118.8	O7A—C2A—N1A	121.00 (14)
C2B—N1B—H1B	118.8	O7A—C2A—N3A	121.13 (14)
C4B—N3B—C2B	121.71 (13)	N1A—C2A—N3A	117.87 (13)
C4B—N3B—H3B	119.1	N8A—C4A—N3A	117.61 (15)
C2B—N3B—H3B	119.1	N8A—C4A—C5A	122.06 (15)
C4B—N8B—H8B1	120.0	N3A—C4A—C5A	120.33 (15)
C4B—N8B—H8B2	120.0	C6A—C5A—C4A	117.66 (15)
H8B1—N8B—H8B2	120.0	C6A—C5A—H5A	121.2
O7B—C2B—N1B	121.34 (14)	C4A—C5A—H5A	121.2
O7B—C2B—N3B	121.59 (14)	C5A—C6A—N1A	121.10 (15)
N1B—C2B—N3B	117.07 (13)	C5A—C6A—H6A	119.4
N8B—C4B—N3B	117.68 (15)	N1A—C6A—H6A	119.4
N8B—C4B—C5B	122.64 (15)	C4—O1—H3	112.6 (11)
N3B—C4B—C5B	119.67 (15)	C1—O3—H3	111.8 (12)
C6B—C5B—C4B	117.72 (15)	O4—C1—O3	123.04 (15)
C6B—C5B—H5B	121.1	O4—C1—C2	116.62 (16)
C4B—C5B—H5B	121.1	O3—C1—C2	120.34 (14)
C5B—C6B—N1B	121.38 (15)	C3—C2—C1	130.78 (17)
C5B—C6B—H6B	119.3	C3—C2—H1	114.6
N1B—C6B—H6B	119.3	C1—C2—H1	114.6
C6A—N1A—C2A	122.13 (14)	C2—C3—C4	130.43 (16)
C6A—N1A—H1A	118.9	C2—C3—H2	114.8
C2A—N1A—H1A	118.9	C4—C3—H2	114.8
C4A—N3A—C2A	120.90 (13)	O2—C4—O1	123.04 (16)
C4A—N8A—H8A1	120.0	O2—C4—C3	117.21 (16)
C4A—N8A—H8A2	120.0	O1—C4—C3	119.74 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O4	0.86	1.89	2.7426 (19)	174
N1B—H1B···O2ⁱ	0.86	1.91	2.7701 (19)	174
N8A—H8A1···O7B	0.86	2.00	2.8582 (19)	178
N8A—H8A2···O7Aⁱⁱ	0.86	2.04	2.8329 (19)	153
N3B—H3B···N3A	0.86	1.98	2.8370 (19)	176
N8B—H8B1···O7A	0.86	1.99	2.8458 (19)	173
N8B—H8B2···O7Bⁱⁱⁱ	0.86	2.06	2.8491 (18)	153
O3—H3···O1	1.17 (2)	1.25 (2)	2.4167 (16)	173 (2)
C6B—H6B···O1ⁱ	0.93	2.50	3.186 (2)	131
C5B—H5B···O2^iv	0.93	2.42	3.330 (2)	165
C5A—H5A···O4ⁱⁱ	0.93	2.37	3.296 (2)	175

Symmetry codes: (i) x+1/2, −y+3/2, z−1/2; (ii) x, y+1, z; (iii) x, y−1, z; (iv) x+1/2, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₄H₆N₃O⁺·C₄H₃O₄⁻·C₄H₅N₃O
M_r	338.29
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	27.3226 (5), 7.3618 (2), 14.6742 (4)
β (°)	93.905 (1)
V (Å³)	2944.77 (13)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.13
Crystal size (mm)	0.3 × 0.15 × 0.1

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3490, 3485, 2603
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.136, 1.07
No. of reflections	3485
No. of parameters	202
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.23

Computer programs: KappaCCD Server Software (Nonius, 1998), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O4	0.86	1.89	2.7426 (19)	173.7
N1B—H1B···O2ⁱ	0.86	1.91	2.7701 (19)	174.2
N8A—H8A1···O7B	0.86	2.00	2.8582 (19)	178.2
N8A—H8A2···O7Aⁱⁱ	0.86	2.04	2.8329 (19)	152.6
N3B—H3B···N3A	0.86	1.98	2.8370 (19)	176.0
N8B—H8B1···O7A	0.86	1.99	2.8458 (19)	172.6
N8B—H8B2···O7Bⁱⁱⁱ	0.86	2.06	2.8491 (18)	152.5
O3—H3···O1	1.17 (2)	1.25 (2)	2.4167 (16)	173 (2)
C6B—H6B···O1ⁱ	0.93	2.50	3.186 (2)	130.5
C5B—H5B···O2^iv	0.93	2.42	3.330 (2)	164.6
C5A—H5A···O4ⁱⁱ	0.93	2.37	3.296 (2)	175.1

Symmetry codes: (i) x+1/2, −y+3/2, z−1/2; (ii) x, y+1, z; (iii) x, y−1, z; (iv) x+1/2, −y+1/2, z−1/2.

Acknowledgements

We wish to thank Dr M. Giorgi, Faculté des Sciences et Techniques de Saint Jérome, Marseille, France, for providing diffraction facilities and le Centre Universitaire de Khenchela for financial support.

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