2-Amino-3-carb­oxy­pyridinium perchlorate

Fadila Berrah; Sofiane Bouacida; Hayet Anana; Thierry Roisnel

doi:10.1107/S1600536812018922

. 2012 May 2;68(Pt 6):o1601–o1602. doi: 10.1107/S1600536812018922

2-Amino-3-carboxypyridinium perchlorate

Fadila Berrah ^a,^*, Sofiane Bouacida ^b, Hayet Anana ^a, Thierry Roisnel ^c

PMCID: PMC3379211 PMID: 22719409

Abstract

The asymmetric unit includes two crystallographically independent equivalents of the title salt, C₆H₇N₂O₂ ⁺·ClO₄ ⁻. The cations and anions form separate layers alternating along the c axis, which are linked by N—H⋯O, O—H⋯O and C—H⋯O hydrogen bonds into a two-dimensional network parallel to (100). Further C—H⋯O contacts connect these layers, forming a three-dimensional network, in which R ₄ ⁴(20) rings and C ₂ ²(11) infinite chains can be identified.

Related literature

For structural studies of hybrid compounds of 2-aminonicotinic acid, see: Akriche & Rzaigui (2007 ▶); Berrah et al. (2011a ▶,b ▶). For related perchlorate compounds, see: Toumi Akriche et al. (2010 ▶); Bendjeddou et al. (2003 ▶). For hydrogen-bond motifs, see: Etter et al. (1990 ▶); Grell et al. (1999 ▶). graphic file with name e-68-o1601-scheme1.jpg

Experimental

Crystal data

C₆H₇N₂O₂ ⁺·ClO₄ ⁻
M _r = 238.59
Monoclinic,
a = 17.3573 (12) Å
b = 5.0800 (4) Å
c = 21.6293 (17) Å
β = 107.239 (2)°
V = 1821.5 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.43 mm⁻¹
T = 150 K
0.48 × 0.17 × 0.08 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▶) T _min = 0.847, T _max = 0.966
13822 measured reflections
4142 independent reflections
3305 reflections with I > 2σ(I)
R _int = 0.044

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.110
S = 1.11
4142 reflections
273 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.40 e Å⁻³

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 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812018922/ld2056sup1.cif

e-68-o1601-sup1.cif^{(27.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812018922/ld2056Isup2.hkl

e-68-o1601-Isup2.hkl^{(198.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812018922/ld2056Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1A—H1A⋯O21	0.82	1.99	2.810 (3)	173
O1B—H1B⋯O42	0.82	1.96	2.779 (3)	176
N2A—H2A⋯O32	0.86	2.24	2.968 (3)	142
N2B—H2B⋯O31	0.86	2.31	3.005 (3)	138
N2B—H2B⋯O22ⁱ	0.86	2.34	2.992 (3)	133
N1A—H11A⋯O22ⁱⁱ	0.86	2.50	3.211 (3)	141
N1A—H11A⋯O32	0.86	2.58	3.231 (3)	133
N1B—H11B⋯O31	0.86	2.32	3.000 (3)	136
N1B—H11B⋯O41ⁱⁱⁱ	0.86	2.54	3.268 (3)	143
N1A—H12A⋯O2Bⁱⁱ	0.86	2.19	2.928 (3)	144
N1B—H12B⋯O2Aⁱⁱⁱ	0.86	2.22	2.971 (3)	145
C4A—H4A⋯O11^iv	0.93	2.57	3.312 (3)	137
C4B—H4B⋯O32^v	0.93	2.53	3.433 (3)	165
C5A—H5A⋯O11^vi	0.93	2.37	3.277 (3)	164
C5B—H5B⋯O12^vii	0.93	2.52	3.450 (3)	177

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) .

Acknowledgments

We are grateful to the LCATM laboratory, Université d’Oum El Bouaghi, Algeria, for financial support.

supplementary crystallographic information

Comment

As a continuation of the systematic studies on synthesis and structural characterization of the products of derivatives of nicotinic acid with inorganic acids, and as an attempt to establish a relationship between the nature of the anion and the resulting hydrogen-bonding pattern, we report here the crystal structure of the title compound obtained by reaction between 2-aminonicotinic and perchloric acids. Related compounds obtained with dihydrogen phosphate, sulfate and nitrate anions, have been reported previously (Akriche & Rzaigui 2007; Berrah et al. 2011a,b).

The dimers of 2-aminonicotinium cations are formed via N—H···O h-bonds (NH of the amine group with the O of the carboxylic group). Similar dimers have been also observed in the structures with dihydrogen phosphate and sulfate anions (Akriche & Rzaigui 2007; Berrah et al. 2011a), while cations in the nitrate structure adopt a different configuration (Berrah et al. 2011b).

In the crystal structure, cationic and anionic layers alternate along the c axis and are linked by intermolecular N—H···O, O—H···O and weak C—H···O hydrogen bonds (see table 1) resulting in a two-dimensional network parallel to (100) (Fig.2). Further C—H···O contacts connect these layers, forming a three-dimensional network in which R₄⁴(20) rings and C₂²(11) infinite chains are generated (Etter et al. 1990; Grell et al. 1999).

Experimental

Colourless crystals of compound (I) were grown by slow evaporation of an aquoes solution of 2-amino-pyridine-3-carboxylic acid and perchloric acid in an 1:1 stoichiometric ratio.