Hydrogen bonding in 2-carboxy­anilinium dihydrogen phosphite at 100 K

Nourredine Benali-Cherif; Fatima Allouche; Amani Direm; Kawther Soudani

doi:10.1107/S1600536809007077

. 2009 Mar 6;65(Pt 4):o664–o665. doi: 10.1107/S1600536809007077

Hydrogen bonding in 2-carboxyanilinium dihydrogen phosphite at 100 K

Nourredine Benali-Cherif ^a,^*, Fatima Allouche ^a, Amani Direm ^a, Kawther Soudani ^a

PMCID: PMC2968775 PMID: 21582409

Abstract

The title compound, C₇H₈NO₂ ⁺·H₂PO₃ ⁻, is formed from alternating layers of organic cations and inorganic anions stacked along the a-axis direction. They are associated via O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonding, giving rise to two different R ₂ ²(8) graph-set motifs and generating a three-dimensional network.

Related literature

For applications of hybrid compounds, see: Kagan et al. (1999 ▶); Mazeaud et al. (2000 ▶); Benali-Cherif, Direm et al. (2007 ▶). For applications of anthranilic acid derivatives, see: He et al. (2003 ▶); Per Wiklund et al. (2004 ▶); Congiu et al. (2005 ▶); Nittoli et al. (2005 ▶). For related structured, see: Bendeif et al. (2003 ▶, 2009 ▶); Benali-Cherif, Allouche et al. (2007 ▶). For graph-set theory, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₇H₈NO₂ ⁺·H₂PO₃ ⁻
M _r = 219.13
Triclinic,
a = 4.8757 (6) Å
b = 9.4597 (6) Å
c = 10.0801 (5) Å
α = 78.929 (3)°
β = 76.058 (4)°
γ = 86.814 (2)°
V = 442.81 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 100 K
0.25 × 0.18 × 0.05 mm

Data collection

Oxford Diffraction Xcalibur Saphire2 diffractometer
Absorption correction: integration (ABSORB; DeTitta, 1985 ▶) T _min = 0.972, T _max = 0.985
11058 measured reflections
2581 independent reflections
2559 reflections with I > 2σ(I)
R _int = 0.035

Refinement

R[F ² > 2σ(F ²)] = 0.033
wR(F ²) = 0.093
S = 1.07
2581 reflections
127 parameters
H-atom parameters not refined
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.24 e Å⁻³

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 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809007077/bg2238sup1.cif

e-65-0o664-sup1.cif^{(15.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809007077/bg2238Isup2.hkl

e-65-0o664-Isup2.hkl^{(124.1KB, hkl)}

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
O1—H1⋯O3ⁱ	0.84	1.77	2.6085 (13)	178
N1—H1A⋯O4	0.91	1.96	2.8589 (14)	169
N1—H1B⋯O4ⁱⁱ	0.91	2.02	2.9160 (13)	169
N1—H1C⋯O4ⁱⁱⁱ	0.91	1.97	2.8740 (14)	173
O5—H5O⋯O3^iv	0.84	1.78	2.6059 (13)	167
C6—H6⋯O5^v	0.95	2.55	3.2542 (15)	132

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

Acknowledgments

We wish to thank Dr C. Lecomte of LCM3B (UMR UHP –CNRS 7036), Faculté des Sciences et Techniques 54506 Vandoeuvre-lès-Nancy CEDEX, for providing diffraction facilities in his laboratory, and le Centre Universitaire de Khenchela for financial support.

supplementary crystallographic information

Comment

The crystal structures of organic-inorganic hybrid materials have been extensively investigated due to their interest in the field of new materials, and the number of reported structures is rapidly growing owing to their applications in medicine, material science and to their electrical, magnetic and optical properties (Kagan et al., 1999; Mazeaud et al., 2000) and the hydrogen bonding richness of these structures. This kind of hydrogen bonding appears in the active sites of several biological systems and is observed in similar previously studied hybrid compounds (Benali-Cherif, Direm et al., 2007).

As well as being a biochemical precursor of the amino acids tryptophan, phenylalanine and tyrosine, anthranilic acid is used as a useful derivating agent for carbohydrate analysis (He et al., 2003). 2-Aminobenzoic acid is present as a part of the core structure of certain alkaloids, synthetic drugs (Per Wiklund et al., 2004), antiinflammatory, anticancer agents (Congiu et al., 2005) and as inhibitor of Hepatitis C NS5B polymerase (Nittoli et al., 2005).

The title compound structure (I) is composed of cationic HOO-C₆H₄—NH₃⁺ and anionic (H₂PO₃^-) groups (Fig.1). All bond lengths and angles of the (H₂PO₃^-) tetrahedra and the o-carboxyanilinium cations are within normal ranges, in a good agreement with those observed in the litterature (Bendeif et al. 2003, Bendeif et al. 2009) and (Benali-Cherif, Allouche et al., 2007), respectively.

The three H atoms of the anilinium group are subsequently involved in extensive N—H···O hydrogen-bonding (Table 1) interactions with O4 being a multiple acceptor of three different phosphite anions, while O3 behaves as double acceptor of hydrogen bonds from one cation, via O1 in the carboxylic group, and one anion, via O5 in the phosphite anion. These interactions give raise to two different R₂²(8) graph set motifs (Bernstein et al. 1995), shown in Fig. 2. In addition, there are intramolecular interactions involving the benzene ring and the carboxylic group ensuring cohesion and stability of the crystal structiure.

Experimental

Crystals of anthranilicium phosphite are prepared by slow evaporation at room temperature of an aqueous solution of 2-aminobenzoic acid and H₃PO₃ in a 1:1 stochiometric ratio.