2-Amino-3-carb­oxy­pyrazin-1-ium perchlorate bis­(2-amino­pyrazin-1-ium-3-carboxyl­ate) monohydrate

Berrah, F.; Bouacida, S.; Bouhraoua, A.; Roisnel, T.

doi:10.1107/S1600536812021071

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Pages o1714-o1715

doi:10.1107/S1600536812021071

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2-Amino-3-carboxypyrazin-1-ium perchlorate bis(2-aminopyrazin-1-ium-3-carboxylate) monohydrate

Fadila Berrah,^a ^* Sofiane Bouacida,^b Ahlem Bouhraoua ^a and Thierry Roisnel ^c

^aLaboratoire de Chimie Appliquée et Technologie des Matériaux (LCATM), Université d'Oum El Bouaghi 04000, Algeria, ^bUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale (CHEMS), Faculté des Sciences Exactes, Université Mentouri Constantine 25000, Algeria, and ^cCentre de Difractométrie X, UMR 6226 CNRS Unité Sciences Chimiques de Rennes, Université de Rennes I, 263 Avenue du Général Leclerc, 35042 Rennes, France
^*Correspondence e-mail: fadilaber@yahoo.fr

(Received 30 April 2012; accepted 9 May 2012; online 12 May 2012)

The asymmetric unit of the title compound, C₅H₆N₃O₂⁺·ClO₄⁻·2C₅H₅N₃O₂·H₂O, comprises two symmetry-independent zwitterions, one cation, one perchlorate anion and one water molecule. In the crystal, the three different types of organic entities are linked by N—H⋯O and N—H⋯N hydrogen bonds, forming undulating sheets parallel to (1-10). These sheets are in turn connected by O—H⋯N and O—H⋯O hydrogen bonds involving perchlorate anions and water molecules, forming a three-dimensional network. Intramolecular N—H⋯O and weak intermolecular C—H⋯O hydrogen bonds are also present.

Related literature

For crystal structures of hybrid compounds obtained from 3-amino-pyrazine 2-carboxylic acid, see: Berrah et al. (2011a ,b ,c ). For related perchlorate compounds, see: Bendjeddou et al. (2003 ); Berrah et al. (2012 ); Toumi Akriche et al.(2010 ).

Experimental

Crystal data

C₅H₆N₃O₂⁺·ClO₄⁻·2C₅H₅N₃O₂·H₂O
M_r = 535.83
Triclinic, $[P \overline 1]$
a = 8.1332 (14) Å
b = 11.816 (2) Å
c = 11.850 (2) Å
α = 95.696 (9)°
β = 108.148 (8)°
γ = 102.416 (8)°
V = 1039.8 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 150 K
0.46 × 0.27 × 0.17 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ) T_min = 0.855, T_max = 0.955
15575 measured reflections
4705 independent reflections
4165 reflections with I > 2σ(I)
R_int = 0.057

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.1
S = 1.04
4705 reflections
332 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.48 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1A—H1A⋯O1W	0.82	1.71	2.5258 (18)	172
O1W—H1W⋯O1Bⁱ	0.88 (2)	1.92 (2)	2.7873 (19)	169 (2)
O1W—H2W⋯O2	0.84 (2)	1.99 (2)	2.8176 (19)	172 (2)
O1W—H1W⋯N3Bⁱ	0.88 (2)	2.56 (2)	3.052 (2)	115.8 (17)
N2B—H2B⋯O1C	0.86	1.92	2.6935 (18)	149
N1C—H11C⋯O2Bⁱⁱ	0.86	2.11	2.958 (2)	170
N2C—H2C⋯O1Bⁱⁱ	0.86	1.76	2.6156 (19)	171
N2A—H2A⋯O2Cⁱⁱⁱ	0.86	1.80	2.6536 (17)	175
N1A—H11A⋯O1Cⁱⁱⁱ	0.86	2.14	2.9340 (19)	153
N1B—H11B⋯O1A	0.86	2.26	2.916 (2)	133
N1B—H11B⋯O1C	0.86	2.44	3.087 (2)	133
N1B—H12B⋯O2B	0.86	2.21	2.814 (2)	127
N1A—H12A⋯O2A	0.86	2.09	2.7038 (19)	128
N1C—H12C⋯O2C	0.86	2.06	2.6734 (19)	128
N2B—H2B⋯N3C	0.86	2.41	3.058 (2)	132
N1B—H12B⋯N3A	0.86	2.41	3.035 (2)	130
N1A—H12A⋯N3B^iv	0.86	2.44	3.152 (2)	140
C4B—H4B⋯O1^v	0.93	2.41	3.267 (2)	153
C4C—H4C⋯O3^vi	0.93	2.45	3.350 (2)	162
C5A—H5A⋯O2B	0.93	2.58	3.336 (2)	138
C5B—H5B⋯O2^v	0.93	2.48	3.145 (2)	129
C5B—H5B⋯O2A^v	0.93	2.48	3.164 (2)	130
Symmetry codes: (i) -x+1, -y, -z+1; (ii) x+1, y+1, z; (iii) -x, -y, -z; (iv) x, y, z-1; (v) x, y, z+1; (vi) -x+2, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2006 ); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2005 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and Mercury (Macrae et al. 2006 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812021071/lh5470sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812021071/lh5470Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812021071/lh5470Isup3.cml

checkCIF report

Comment top

N-heterocyclic compounds such as pyrazine and its derivatives encompass a variety of potential hydrogen donors and acceptors which makes them interesting units to built new edifices involving original hydrogen-bonding schemes. As a continuation of our systematic studies concerning the synthesis and structural characterization of organic-inorganic hybrids and in attempts to establish a relationship between the nature of the anion used and hydrogen-bonding pattern encountered in these structures, we report herein the crystal structure of the compound 2-Amino-3-carboxypyrazin-1-ium perchlorate bis(2-aminopyrazin-1-ium 3-carboxylate) monohydrate. Related compounds obtained with nitrate, sulfate and dihydrogen phosphate anions have been reported (Berrah et al. 2011a,b,c).

The asymmetric unit, shown in Fig.1, comprises two symmetry independent zwitterions (B and C), one cation (A), one perchlorate anion and one water molecule. Bonds distances and angles in the three organic entities are comparable to that encountered in similar structures (Berrah et al. 2011a,b,c) except for the C—O distances in the carboxylic group: C—O distances are 1.2524 (19) and 1.2553 (19) Å in (B) and 1.2418 (19) and 1.2631 (19) Å in (C), due to the transfer of the carboxylic group proton to the hetero-ring nitrogen atom. Perchlorate anions present quite regular tetrahedral geometry (Cl—O distances range from 1.4279 (13) to 1.4528 (12) Å and angles from 108.67 (8) to 110.11 (9)°) and are comparable to that reported in the literature (Bendjeddou et al. 2003; Berrah et al.2012; Toumi Akriche et al.2010).

All components of the structure are involved in an interesting hydrogen bond system in which all potential donors and acceptors are implicated: the H₂O molecule, the two 2-Aminopyrazin-1-ium 3-carboxylate zwitterions (B and C) and the 2-Amino-3-carboxypyrazin-1-ium cation (A) act as both hydrogen bond donors and acceptors (table 1). An extensive H-bonding system between the three different organic entities, allows development of wave-like extended chains which intersect to form double-sheets parallel to (110) (Fig.2 and Fig.3). Perchlorate anions and water molecules connect these double-sheets to generate a three-dimensional network (Fig.2 and Fig.3).

Related literature top

For crystal structures of hybrid compounds obtained from 3-amino-pyrazine 2-carboxylic acid, see: Berrah et al. (2011a,b,c). For related perchlorate compounds, see: Bendjeddou et al. (2003); Berrah et al. (2012); Toumi Akriche et al.(2010).

Experimental top

The title compound was obtained by reacting 3-amino-pyrazine 2-carboxylic acid with some excess of perchloric acid in aqueous solution. Slow evaporation allows growth of well formed colourless prismatic crystals.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SIR2002 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al. 2006); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen bonds are shown as dashed lines.
	Fig. 2. A partial view of one extended double-sheet showing wave-like chains and H-bonds between the different components. Hydrogen bonds are shown as dashed lines.
	Fig. 3. A view of part of the packing of (I) showing how double-sheets are linked via perchlorate anions and water molecules. Hydrogen bonds are shown as dashed lines.

2-Amino-3-carboxypyrazin-1-ium perchlorate bis(2-aminopyrazin-1-ium-3-carboxylate) monohydrate top

Crystal data top

C₅H₆N₃O₂⁺·ClO₄⁻·2C₅H₅N₃O₂·H₂O	Z = 2
M_r = 535.83	F(000) = 552
Triclinic, P1	D_x = 1.712 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1332 (14) Å	Cell parameters from 7298 reflections
b = 11.816 (2) Å	θ = 2.7–27.4°
c = 11.850 (2) Å	µ = 0.27 mm⁻¹
α = 95.696 (9)°	T = 150 K
β = 108.148 (8)°	Prism, colourless
γ = 102.416 (8)°	0.46 × 0.27 × 0.17 mm
V = 1039.8 (3) Å³

Data collection top

Bruker APEXII diffractometer	4165 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.057
CCD rotation images, thin slices scans	θ_max = 27.5°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −10→10
T_min = 0.855, T_max = 0.955	k = −15→15
15575 measured reflections	l = −14→15
4705 independent reflections

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.1	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0379P)² + 0.495P] where P = (F_o² + 2F_c²)/3
4705 reflections	(Δ/σ)_max = 0.001
332 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.48 e Å⁻³

Crystal data top

C₅H₆N₃O₂⁺·ClO₄⁻·2C₅H₅N₃O₂·H₂O	γ = 102.416 (8)°
M_r = 535.83	V = 1039.8 (3) Å³
Triclinic, P1	Z = 2
a = 8.1332 (14) Å	Mo Kα radiation
b = 11.816 (2) Å	µ = 0.27 mm⁻¹
c = 11.850 (2) Å	T = 150 K
α = 95.696 (9)°	0.46 × 0.27 × 0.17 mm
β = 108.148 (8)°

Data collection top

Bruker APEXII diffractometer	4705 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	4165 reflections with I > 2σ(I)
T_min = 0.855, T_max = 0.955	R_int = 0.057
15575 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.1	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.39 e Å⁻³
4705 reflections	Δρ_min = −0.48 e Å⁻³
332 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
Cl1	0.69001 (5)	0.36663 (3)	−0.00929 (3)	0.01747 (11)
O3	0.68759 (17)	0.43096 (11)	0.09976 (11)	0.0282 (3)
C2A	0.07122 (19)	−0.13735 (13)	0.05029 (13)	0.0142 (3)
O2	0.62112 (16)	0.24144 (10)	−0.01437 (11)	0.0248 (3)
O1A	0.32377 (15)	0.00920 (10)	0.18281 (10)	0.0214 (3)
H1A	0.4049	0.0661	0.1869	0.032*
O1W	0.55592 (16)	0.19617 (10)	0.19895 (12)	0.0222 (3)
H1W	0.663 (3)	0.2094 (19)	0.254 (2)	0.033*
H2W	0.566 (3)	0.205 (2)	0.132 (2)	0.033*
O2C	0.40678 (15)	0.39784 (9)	0.29630 (10)	0.0185 (2)
N2C	0.88489 (17)	0.53957 (11)	0.58581 (12)	0.0170 (3)
H2C	0.9651	0.6013	0.588	0.02*
O1	0.57705 (18)	0.40133 (11)	−0.11220 (11)	0.0298 (3)
N3C	0.63598 (17)	0.34284 (12)	0.58168 (12)	0.0176 (3)
O1B	0.11825 (16)	−0.26089 (10)	0.61036 (11)	0.0235 (3)
C5B	0.3196 (2)	0.08607 (14)	0.75159 (14)	0.0183 (3)
H5B	0.3426	0.1123	0.833	0.022*
C5C	0.7831 (2)	0.38892 (15)	0.68069 (15)	0.0197 (3)
H5C	0.7998	0.3523	0.7478	0.024*
O4	0.86893 (17)	0.38880 (12)	−0.01070 (14)	0.0359 (3)
N1A	−0.01642 (18)	−0.16806 (12)	−0.17083 (12)	0.0212 (3)
H11A	−0.0909	−0.2062	−0.2398	0.025*
H12A	0.0748	−0.1132	−0.1671	0.025*
N2B	0.34558 (17)	0.12346 (11)	0.56691 (12)	0.0176 (3)
H2B	0.3852	0.1715	0.5257	0.021*
C1C	0.4396 (2)	0.34074 (13)	0.38055 (14)	0.0156 (3)
C4B	0.3817 (2)	0.16113 (14)	0.68530 (14)	0.0186 (3)
H4B	0.4485	0.2378	0.7214	0.022*
C2C	0.61173 (19)	0.39387 (13)	0.48635 (14)	0.0147 (3)
C3C	0.7406 (2)	0.49782 (13)	0.48389 (14)	0.0150 (3)
O2B	−0.00600 (16)	−0.22021 (10)	0.42749 (10)	0.0239 (3)
O1C	0.34056 (15)	0.24560 (10)	0.38619 (10)	0.0219 (3)
C3A	−0.04216 (19)	−0.19367 (13)	−0.07064 (14)	0.0150 (3)
N2A	−0.18714 (16)	−0.28048 (11)	−0.08043 (11)	0.0152 (3)
H2A	−0.2602	−0.3146	−0.1513	0.018*
N1C	0.72791 (18)	0.55293 (12)	0.39109 (12)	0.0199 (3)
H11C	0.8106	0.6143	0.3961	0.024*
H12C	0.6369	0.5274	0.3257	0.024*
C5A	−0.1068 (2)	−0.26064 (14)	0.12868 (14)	0.0178 (3)
H5A	−0.1291	−0.2857	0.1957	0.021*
N3B	0.22488 (17)	−0.02635 (12)	0.70059 (12)	0.0173 (3)
C1B	0.0919 (2)	−0.19231 (14)	0.53518 (14)	0.0172 (3)
O2A	0.25539 (16)	0.00695 (10)	−0.01483 (10)	0.0239 (3)
C2B	0.1914 (2)	−0.06368 (13)	0.58521 (14)	0.0156 (3)
N3A	0.03789 (17)	−0.17121 (11)	0.14528 (12)	0.0164 (3)
C1A	0.2274 (2)	−0.03376 (13)	0.06933 (14)	0.0154 (3)
C4C	0.9077 (2)	0.48821 (15)	0.68396 (15)	0.0200 (3)
H4C	1.0073	0.52	0.7532	0.024*
N1B	0.2181 (2)	−0.01866 (13)	0.39418 (13)	0.0263 (3)
H11B	0.2591	0.0311	0.3549	0.032*
H12B	0.1569	−0.0888	0.3577	0.032*
C3B	0.2491 (2)	0.01272 (14)	0.51060 (14)	0.0170 (3)
C4A	−0.2213 (2)	−0.31536 (13)	0.01601 (14)	0.0168 (3)
H4A	−0.3216	−0.376	0.0063	0.02*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.01646 (19)	0.01438 (19)	0.0198 (2)	0.00210 (14)	0.00545 (15)	0.00173 (14)
O3	0.0371 (7)	0.0237 (6)	0.0195 (6)	0.0060 (5)	0.0069 (5)	−0.0027 (5)
C2A	0.0137 (7)	0.0142 (7)	0.0136 (7)	0.0036 (6)	0.0033 (6)	0.0016 (6)
O2	0.0290 (6)	0.0143 (6)	0.0267 (7)	−0.0020 (5)	0.0092 (5)	0.0016 (5)
O1A	0.0193 (6)	0.0231 (6)	0.0145 (6)	−0.0055 (4)	0.0039 (4)	0.0011 (5)
O1W	0.0196 (6)	0.0226 (6)	0.0202 (6)	−0.0005 (5)	0.0047 (5)	0.0046 (5)
O2C	0.0207 (6)	0.0158 (5)	0.0141 (5)	0.0003 (4)	0.0019 (4)	0.0031 (4)
N2C	0.0142 (6)	0.0147 (6)	0.0187 (7)	−0.0012 (5)	0.0050 (5)	0.0012 (5)
O1	0.0366 (7)	0.0292 (7)	0.0208 (6)	0.0125 (6)	0.0033 (5)	0.0057 (5)
N3C	0.0171 (6)	0.0169 (7)	0.0171 (7)	0.0018 (5)	0.0052 (5)	0.0038 (5)
O1B	0.0256 (6)	0.0160 (6)	0.0206 (6)	−0.0040 (5)	0.0023 (5)	0.0050 (5)
C5B	0.0214 (8)	0.0167 (8)	0.0134 (7)	0.0013 (6)	0.0044 (6)	0.0004 (6)
C5C	0.0184 (8)	0.0233 (8)	0.0156 (8)	0.0037 (6)	0.0036 (6)	0.0062 (6)
O4	0.0208 (6)	0.0277 (7)	0.0630 (10)	0.0046 (5)	0.0204 (7)	0.0096 (7)
N1A	0.0205 (7)	0.0232 (7)	0.0126 (7)	−0.0041 (5)	0.0026 (5)	0.0016 (5)
N2B	0.0201 (7)	0.0144 (6)	0.0180 (7)	−0.0002 (5)	0.0084 (5)	0.0058 (5)
C1C	0.0167 (7)	0.0146 (7)	0.0137 (7)	0.0004 (6)	0.0057 (6)	0.0006 (6)
C4B	0.0206 (8)	0.0136 (7)	0.0171 (8)	−0.0005 (6)	0.0045 (6)	−0.0011 (6)
C2C	0.0151 (7)	0.0126 (7)	0.0154 (7)	0.0011 (6)	0.0058 (6)	0.0015 (6)
C3C	0.0156 (7)	0.0131 (7)	0.0155 (7)	0.0017 (6)	0.0063 (6)	0.0003 (6)
O2B	0.0263 (6)	0.0210 (6)	0.0156 (6)	−0.0051 (5)	0.0031 (5)	0.0006 (5)
O1C	0.0221 (6)	0.0186 (6)	0.0165 (6)	−0.0066 (4)	0.0029 (5)	0.0036 (4)
C3A	0.0148 (7)	0.0153 (7)	0.0147 (7)	0.0046 (6)	0.0043 (6)	0.0022 (6)
N2A	0.0139 (6)	0.0154 (6)	0.0127 (6)	0.0018 (5)	0.0016 (5)	0.0007 (5)
N1C	0.0192 (7)	0.0173 (7)	0.0176 (7)	−0.0042 (5)	0.0040 (5)	0.0051 (5)
C5A	0.0190 (7)	0.0193 (8)	0.0152 (8)	0.0019 (6)	0.0080 (6)	0.0035 (6)
N3B	0.0182 (6)	0.0166 (7)	0.0153 (7)	0.0011 (5)	0.0053 (5)	0.0034 (5)
C1B	0.0157 (7)	0.0164 (8)	0.0172 (8)	−0.0014 (6)	0.0070 (6)	0.0009 (6)
O2A	0.0270 (6)	0.0226 (6)	0.0164 (6)	−0.0036 (5)	0.0056 (5)	0.0055 (5)
C2B	0.0148 (7)	0.0155 (7)	0.0142 (7)	0.0002 (6)	0.0043 (6)	0.0020 (6)
N3A	0.0170 (6)	0.0171 (7)	0.0142 (6)	0.0032 (5)	0.0053 (5)	0.0022 (5)
C1A	0.0152 (7)	0.0150 (7)	0.0143 (7)	0.0035 (6)	0.0036 (6)	0.0003 (6)
C4C	0.0173 (7)	0.0226 (8)	0.0161 (8)	0.0035 (6)	0.0025 (6)	0.0002 (6)
N1B	0.0368 (8)	0.0218 (7)	0.0159 (7)	−0.0043 (6)	0.0116 (6)	0.0017 (6)
C3B	0.0166 (7)	0.0163 (8)	0.0157 (8)	0.0008 (6)	0.0048 (6)	0.0027 (6)
C4A	0.0150 (7)	0.0149 (7)	0.0202 (8)	0.0016 (6)	0.0072 (6)	0.0029 (6)

Geometric parameters (Å, º) top

Cl1—O4	1.4279 (13)	N2B—C4B	1.347 (2)
Cl1—O1	1.4362 (13)	N2B—C3B	1.354 (2)
Cl1—O3	1.4406 (13)	N2B—H2B	0.86
Cl1—O2	1.4528 (12)	C1C—O1C	1.2553 (19)
C2A—N3A	1.317 (2)	C1C—C2C	1.516 (2)
C2A—C3A	1.439 (2)	C4B—H4B	0.93
C2A—C1A	1.504 (2)	C2C—C3C	1.442 (2)
O1A—C1A	1.3103 (18)	C3C—N1C	1.321 (2)
O1A—H1A	0.82	O2B—C1B	1.2418 (19)
O1W—H1W	0.88 (2)	C3A—N2A	1.352 (2)
O1W—H2W	0.84 (2)	N2A—C4A	1.340 (2)
O2C—C1C	1.2524 (19)	N2A—H2A	0.86
N2C—C4C	1.345 (2)	N1C—H11C	0.86
N2C—C3C	1.353 (2)	N1C—H12C	0.86
N2C—H2C	0.86	C5A—N3A	1.349 (2)
N3C—C2C	1.314 (2)	C5A—C4A	1.365 (2)
N3C—C5C	1.350 (2)	C5A—H5A	0.93
O1B—C1B	1.2631 (19)	N3B—C2B	1.317 (2)
C5B—N3B	1.354 (2)	C1B—C2B	1.520 (2)
C5B—C4B	1.361 (2)	O2A—C1A	1.2112 (19)
C5B—H5B	0.93	C2B—C3B	1.432 (2)
C5C—C4C	1.364 (2)	C4C—H4C	0.93
C5C—H5C	0.93	N1B—C3B	1.321 (2)
N1A—C3A	1.321 (2)	N1B—H11B	0.86
N1A—H11A	0.86	N1B—H12B	0.86
N1A—H12A	0.86	C4A—H4A	0.93

O4—Cl1—O1	110.11 (9)	N1C—C3C—C2C	125.21 (14)
O4—Cl1—O3	110.07 (8)	N2C—C3C—C2C	115.84 (14)
O1—Cl1—O3	109.55 (8)	N1A—C3A—N2A	118.17 (14)
O4—Cl1—O2	109.26 (8)	N1A—C3A—C2A	125.89 (14)
O1—Cl1—O2	108.67 (8)	N2A—C3A—C2A	115.95 (13)
O3—Cl1—O2	109.15 (8)	C4A—N2A—C3A	122.52 (13)
N3A—C2A—C3A	121.68 (14)	C4A—N2A—H2A	118.7
N3A—C2A—C1A	118.80 (13)	C3A—N2A—H2A	118.7
C3A—C2A—C1A	119.47 (13)	C3C—N1C—H11C	120
C1A—O1A—H1A	109.5	C3C—N1C—H12C	120
H1W—O1W—H2W	110 (2)	H11C—N1C—H12C	120
C4C—N2C—C3C	122.50 (14)	N3A—C5A—C4A	121.69 (14)
C4C—N2C—H2C	118.8	N3A—C5A—H5A	119.2
C3C—N2C—H2C	118.8	C4A—C5A—H5A	119.2
C2C—N3C—C5C	119.78 (14)	C2B—N3B—C5B	119.75 (14)
N3B—C5B—C4B	120.86 (15)	O2B—C1B—O1B	126.42 (15)
N3B—C5B—H5B	119.6	O2B—C1B—C2B	118.62 (14)
C4B—C5B—H5B	119.6	O1B—C1B—C2B	114.96 (13)
N3C—C5C—C4C	121.16 (15)	N3B—C2B—C3B	121.61 (14)
N3C—C5C—H5C	119.4	N3B—C2B—C1B	117.00 (14)
C4C—C5C—H5C	119.4	C3B—C2B—C1B	121.38 (14)
C3A—N1A—H11A	120	C2A—N3A—C5A	119.10 (13)
C3A—N1A—H12A	120	O2A—C1A—O1A	124.13 (14)
H11A—N1A—H12A	120	O2A—C1A—C2A	121.45 (14)
C4B—N2B—C3B	122.34 (14)	O1A—C1A—C2A	114.38 (13)
C4B—N2B—H2B	118.8	N2C—C4C—C5C	119.23 (14)
C3B—N2B—H2B	118.8	N2C—C4C—H4C	120.4
O2C—C1C—O1C	125.77 (14)	C5C—C4C—H4C	120.4
O2C—C1C—C2C	116.62 (13)	C3B—N1B—H11B	120
O1C—C1C—C2C	117.59 (13)	C3B—N1B—H12B	120
N2B—C4B—C5B	119.43 (14)	H11B—N1B—H12B	120
N2B—C4B—H4B	120.3	N1B—C3B—N2B	119.36 (14)
C5B—C4B—H4B	120.3	N1B—C3B—C2B	124.66 (15)
N3C—C2C—C3C	121.48 (14)	N2B—C3B—C2B	115.96 (14)
N3C—C2C—C1C	116.98 (13)	N2A—C4A—C5A	119.01 (14)
C3C—C2C—C1C	121.52 (13)	N2A—C4A—H4A	120.5
N1C—C3C—N2C	118.95 (14)	C5A—C4A—H4A	120.5

C2C—N3C—C5C—C4C	0.2 (2)	C5B—N3B—C2B—C1B	177.24 (13)
C3B—N2B—C4B—C5B	−0.1 (2)	O2B—C1B—C2B—N3B	150.06 (15)
N3B—C5B—C4B—N2B	1.2 (2)	O1B—C1B—C2B—N3B	−29.6 (2)
C5C—N3C—C2C—C3C	0.9 (2)	O2B—C1B—C2B—C3B	−31.1 (2)
C5C—N3C—C2C—C1C	−177.26 (14)	O1B—C1B—C2B—C3B	149.24 (15)
O2C—C1C—C2C—N3C	171.42 (14)	C3A—C2A—N3A—C5A	−0.3 (2)
O1C—C1C—C2C—N3C	−6.8 (2)	C1A—C2A—N3A—C5A	177.01 (13)
O2C—C1C—C2C—C3C	−6.8 (2)	C4A—C5A—N3A—C2A	−1.3 (2)
O1C—C1C—C2C—C3C	175.03 (14)	N3A—C2A—C1A—O2A	−173.93 (14)
C4C—N2C—C3C—N1C	−179.80 (14)	C3A—C2A—C1A—O2A	3.5 (2)
C4C—N2C—C3C—C2C	−0.2 (2)	N3A—C2A—C1A—O1A	3.9 (2)
N3C—C2C—C3C—N1C	178.63 (15)	C3A—C2A—C1A—O1A	−178.67 (13)
C1C—C2C—C3C—N1C	−3.3 (2)	C3C—N2C—C4C—C5C	1.3 (2)
N3C—C2C—C3C—N2C	−0.9 (2)	N3C—C5C—C4C—N2C	−1.3 (2)
C1C—C2C—C3C—N2C	177.19 (13)	C4B—N2B—C3B—N1B	179.88 (15)
N3A—C2A—C3A—N1A	−177.91 (14)	C4B—N2B—C3B—C2B	−1.7 (2)
C1A—C2A—C3A—N1A	4.8 (2)	N3B—C2B—C3B—N1B	−179.13 (16)
N3A—C2A—C3A—N2A	2.0 (2)	C1B—C2B—C3B—N1B	2.1 (2)
C1A—C2A—C3A—N2A	−175.33 (12)	N3B—C2B—C3B—N2B	2.5 (2)
N1A—C3A—N2A—C4A	177.75 (14)	C1B—C2B—C3B—N2B	−176.22 (13)
C2A—C3A—N2A—C4A	−2.1 (2)	C3A—N2A—C4A—C5A	0.7 (2)
C4B—C5B—N3B—C2B	−0.3 (2)	N3A—C5A—C4A—N2A	1.1 (2)
C5B—N3B—C2B—C3B	−1.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···O1W	0.82	1.71	2.5258 (18)	172
O1W—H1W···O1Bⁱ	0.88 (2)	1.92 (2)	2.7873 (19)	169 (2)
O1W—H2W···O2	0.84 (2)	1.99 (2)	2.8176 (19)	172 (2)
O1W—H1W···N3Bⁱ	0.88 (2)	2.56 (2)	3.052 (2)	115.8 (17)
N2B—H2B···O1C	0.86	1.92	2.6935 (18)	149
N1C—H11C···O2Bⁱⁱ	0.86	2.11	2.958 (2)	170
N2C—H2C···O1Bⁱⁱ	0.86	1.76	2.6156 (19)	171
N2A—H2A···O2Cⁱⁱⁱ	0.86	1.80	2.6536 (17)	175
N1A—H11A···O1Cⁱⁱⁱ	0.86	2.14	2.9340 (19)	153
N1B—H11B···O1A	0.86	2.26	2.916 (2)	133
N1B—H11B···O1C	0.86	2.44	3.087 (2)	133
N1B—H12B···O2B	0.86	2.21	2.814 (2)	127
N1A—H12A···O2A	0.86	2.09	2.7038 (19)	128
N1C—H12C···O2C	0.86	2.06	2.6734 (19)	128
N2B—H2B···N3C	0.86	2.41	3.058 (2)	132
N1B—H12B···N3A	0.86	2.41	3.035 (2)	130
N1A—H12A···N3B^iv	0.86	2.44	3.152 (2)	140
C4B—H4B···O1^v	0.93	2.41	3.267 (2)	153
C4C—H4C···O3^vi	0.93	2.45	3.350 (2)	162
C5A—H5A···O2B	0.93	2.58	3.336 (2)	138
C5B—H5B···O2^v	0.93	2.48	3.145 (2)	129
C5B—H5B···O2A^v	0.93	2.48	3.164 (2)	130

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

Experimental details

Crystal data
Chemical formula	C₅H₆N₃O₂⁺·ClO₄⁻·2C₅H₅N₃O₂·H₂O
M_r	535.83
Crystal system, space group	Triclinic, P1
Temperature (K)	150
a, b, c (Å)	8.1332 (14), 11.816 (2), 11.850 (2)
α, β, γ (°)	95.696 (9), 108.148 (8), 102.416 (8)
V (Å³)	1039.8 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.46 × 0.27 × 0.17

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2002)
T_min, T_max	0.855, 0.955
No. of measured, independent and observed [I > 2σ(I)] reflections	15575, 4705, 4165
R_int	0.057
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.1, 1.04
No. of reflections	4705
No. of parameters	332
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.48

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SIR2002 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al. 2006), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···O1W	0.82	1.71	2.5258 (18)	172
O1W—H1W···O1Bⁱ	0.88 (2)	1.92 (2)	2.7873 (19)	169 (2)
O1W—H2W···O2	0.84 (2)	1.99 (2)	2.8176 (19)	172 (2)
O1W—H1W···N3Bⁱ	0.88 (2)	2.56 (2)	3.052 (2)	115.8 (17)
N2B—H2B···O1C	0.86	1.92	2.6935 (18)	149
N1C—H11C···O2Bⁱⁱ	0.86	2.11	2.958 (2)	170
N2C—H2C···O1Bⁱⁱ	0.86	1.76	2.6156 (19)	171
N2A—H2A···O2Cⁱⁱⁱ	0.86	1.80	2.6536 (17)	175
N1A—H11A···O1Cⁱⁱⁱ	0.86	2.14	2.9340 (19)	153
N1B—H11B···O1A	0.86	2.26	2.916 (2)	133
N1B—H11B···O1C	0.86	2.44	3.087 (2)	133
N1B—H12B···O2B	0.86	2.21	2.814 (2)	127
N1A—H12A···O2A	0.86	2.09	2.7038 (19)	128
N1C—H12C···O2C	0.86	2.06	2.6734 (19)	128
N2B—H2B···N3C	0.86	2.41	3.058 (2)	132
N1B—H12B···N3A	0.86	2.41	3.035 (2)	130
N1A—H12A···N3B^iv	0.86	2.44	3.152 (2)	140
C4B—H4B···O1^v	0.93	2.41	3.267 (2)	153
C4C—H4C···O3^vi	0.93	2.45	3.350 (2)	162
C5A—H5A···O2B	0.93	2.58	3.336 (2)	138
C5B—H5B···O2^v	0.93	2.48	3.145 (2)	129
C5B—H5B···O2A^v	0.93	2.48	3.164 (2)	130

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

Acknowledgements

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

References

Bendjeddou, L., Cherouana, A., Berrah, F. & Benali-Cherif, N. (2003). Acta Cryst. E59, o574–o576. Web of Science CSD CrossRef IUCr Journals Google Scholar
Berrah, F., Bouacida, S., Anana, H. & Roisnel, T. (2012). Acta Cryst. E68, o1601–o1602. CSD CrossRef IUCr Journals Google Scholar
Berrah, F., Bouacida, S. & Roisnel, T. (2011c). Acta Cryst. E67, o1409–o1410. Web of Science CSD CrossRef IUCr Journals Google Scholar
Berrah, F., Ouakkaf, A., Bouacida, S. & Roisnel, T. (2011a). Acta Cryst. E67, o525–o526. Web of Science CrossRef IUCr Journals Google Scholar
Berrah, F., Ouakkaf, A., Bouacida, S. & Roisnel, T. (2011b). Acta Cryst. E67, o677–o678. Web of Science CrossRef IUCr Journals Google Scholar
Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2002). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Toumi Akriche, S., Rzaigui, M., Al-Hokbany, N. & Mahfouz, R. M. (2010). Acta Cryst. E66, o300. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 68| Part 6| June 2012| Pages o1714-o1715

doi:10.1107/S1600536812021071

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2-Amino-3-carb­­oxy­pyrazin-1-ium perchlorate bis­­(2-amino­pyrazin-1-ium-3-carboxyl­ate) monohydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-Amino-3-carboxypyrazin-1-ium perchlorate bis(2-aminopyrazin-1-ium-3-carboxylate) monohydrate