3-Cyano­anilinium nitrate

Bo Wang

doi:10.1107/S1600536809034886

. 2009 Sep 9;65(Pt 10):o2395. doi: 10.1107/S1600536809034886

3-Cyanoanilinium nitrate

Bo Wang ^a,^*

PMCID: PMC2970298 PMID: 21577858

Abstract

In the cation of the title compound, C₇H₇N₂ ⁺·NO₃ ⁻, the nitrile group and the benzene ring are almost coplanar (r.m.s. deviation = 0.006 Å). In the crystal, the ions are connected by bifurcated N—H⋯(O,O) hydrogen bonds, forming a two-dimensional network parallel to (001).

Related literature

For the applications of metal-organic coordination compounds, see: Fu et al. (2007 ▶); Chen et al. (2001 ▶); Fu & Xiong (2008 ▶); Xiong et al. (1999 ▶); Xie et al. (2003 ▶); Zhao et al. (2004 ▶). For nitrile derivatives, see: Fu et al. (2008 ▶); Wang et al. 2002 ▶.

Experimental

Crystal data

C₇H₇N₂ ⁺·NO₃ ⁻
M _r = 181.16
Orthorhombic,
a = 10.210 (2) Å
b = 10.812 (2) Å
c = 15.398 (3) Å
V = 1699.8 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 298 K
0.40 × 0.25 × 0.20 mm

Data collection

Rigaku Mercury2 diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T _min = 0.94, T _max = 1.00
15905 measured reflections
1871 independent reflections
1456 reflections with I > 2σ(I)
R _int = 0.062

Refinement

R[F ² > 2σ(F ²)] = 0.052
wR(F ²) = 0.141
S = 1.14
1871 reflections
120 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809034886/ci2892sup1.cif

e-65-o2395-sup1.cif^{(13.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809034886/ci2892Isup2.hkl

e-65-o2395-Isup2.hkl^{(92.2KB, 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
N2—H2A⋯O3ⁱ	0.89	2.22	3.104 (2)	173
N2—H2A⋯O1ⁱ	0.89	2.44	3.107 (2)	133
N2—H2B⋯O2ⁱⁱ	0.89	2.06	2.859 (2)	150
N2—H2B⋯O3ⁱⁱ	0.89	2.25	3.049 (2)	149
N2—H2C⋯O2	0.89	1.85	2.738 (2)	172
N2—H2C⋯O1	0.89	2.56	3.090 (2)	119

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

This work was supported by a start-up grant from Southeast University to Professor Ren-Gen Xiong.

supplementary crystallographic information

Comment

The construction of metal-organic coordination compounds has attracted much attention owing to potential functions, such as permittivity, fluorescence, magnetism and optical properties (Fu et al., 2007; Chen et al., 2001; Fu & Xiong, 2008; Xie et al., 2003; Zhao et al., 2004; Xiong et al., 1999). Nitrile derivatives are a class of excellent ligands for the construction of novel metal-organic frameworks (Wang et al. 2002; Fu et al., 2008). We report here the crystal structure of the title compound, 3-cyanoanilinium nitrate.

In the 3-cyanoanilinium cation (Fig.1), the nitrile group and the benzene ring are coplanar. The nitrile group C1≡N1 bond length of 1.102 (3) Å is within the normal range.

In the crystal structure, all the amine group H atoms are involved in N—H···O hydrogen bonds (Table 1) with O atoms of the NO₃^- anion. These hydrogen bonds link the ionic units into a two-dimensional network (Fig. 2) parallel to the (001) plane.

Experimental

The commercial 3-aminobenzonitrile (3 mmol, 0.55 g) and HNO₃ (0.5 ml) were dissolved in ethanol (20 ml). Colourless block-shaped crystals of the title compound suitable for X-ray analysis were obtained by slow evaporation at room temperature.