3-Cyano-anilinium nitrate.

In the cation of the title compound, C(7)H(7)N(2) (+)·NO(3) (-), 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 = 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

Δρmax = 0.21 e Å−3

Δρmin = −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.

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

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

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

C7H7N2+·NO3−	F(000) = 752
Mr = 181.16	Dx = 1.416 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1456 reflections
a = 10.210 (2) Å	θ = 3.1–27.5°
b = 10.812 (2) Å	µ = 0.11 mm−1
c = 15.398 (3) Å	T = 298 K
V = 1699.8 (6) Å3	Block, colourless
Z = 8	0.40 × 0.25 × 0.20 mm

Rigaku Mercury2 diffractometer	1871 independent reflections
Radiation source: fine-focus sealed tube	1456 reflections with I > 2σ(I)
graphite	Rint = 0.062
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.1°
CCD profile fitting scans	h = −13→13
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −13→13
Tmin = 0.94, Tmax = 1.00	l = −19→19
15905 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.052	H-atom parameters constrained
wR(F2) = 0.141	w = 1/[σ2(Fo2) + (0.059P)2 + 0.3685P] where P = (Fo2 + 2Fc2)/3
S = 1.14	(Δ/σ)max = 0.001
1871 reflections	Δρmax = 0.21 e Å−3
120 parameters	Δρmin = −0.19 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.021 (3)

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 > 2sigma(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.

	x	y	z	Uiso*/Ueq
N1	0.06292 (19)	0.5067 (2)	0.39061 (13)	0.0724 (6)
N2	0.39497 (14)	0.44355 (16)	0.69503 (9)	0.0435 (4)
H2A	0.4110	0.5239	0.7016	0.065*
H2B	0.4620	0.4001	0.7158	0.065*
H2C	0.3224	0.4236	0.7238	0.065*
C1	0.1482 (2)	0.4737 (2)	0.42791 (13)	0.0526 (5)
C2	0.25733 (17)	0.43017 (19)	0.47337 (11)	0.0443 (5)
C3	0.27221 (17)	0.45958 (18)	0.56150 (11)	0.0420 (5)
H3	0.2108	0.5080	0.5904	0.050*
C4	0.37764 (16)	0.41559 (17)	0.60241 (11)	0.0382 (4)
C5	0.46585 (19)	0.34385 (19)	0.55934 (12)	0.0488 (5)
H5	0.5382	0.3131	0.5890	0.059*
C6	0.4502 (2)	0.3155 (2)	0.47200 (13)	0.0568 (6)
H6	0.5119	0.2669	0.4436	0.068*
C7	0.3461 (2)	0.3585 (2)	0.42905 (12)	0.0538 (5)
H7	0.3339	0.3403	0.3706	0.065*
O1	0.23542 (15)	0.20195 (16)	0.71257 (11)	0.0701 (5)
O2	0.16047 (13)	0.37804 (14)	0.76798 (10)	0.0594 (5)
O3	0.04000 (13)	0.21817 (14)	0.73494 (10)	0.0592 (5)
N3	0.14567 (15)	0.26571 (16)	0.73782 (10)	0.0449 (4)

	U11	U22	U33	U12	U13	U23
N1	0.0625 (12)	0.1071 (17)	0.0476 (11)	0.0072 (12)	−0.0138 (9)	−0.0010 (11)
N2	0.0413 (8)	0.0563 (10)	0.0328 (8)	0.0053 (7)	−0.0013 (6)	−0.0047 (7)
C1	0.0517 (11)	0.0722 (14)	0.0339 (10)	−0.0038 (10)	−0.0043 (9)	−0.0017 (9)
C2	0.0432 (10)	0.0547 (12)	0.0351 (9)	−0.0056 (8)	−0.0034 (7)	0.0006 (8)
C3	0.0382 (9)	0.0536 (11)	0.0341 (9)	0.0008 (8)	0.0015 (7)	−0.0030 (8)
C4	0.0401 (9)	0.0440 (10)	0.0306 (9)	−0.0018 (8)	0.0004 (7)	−0.0021 (7)
C5	0.0473 (10)	0.0588 (12)	0.0403 (10)	0.0103 (9)	0.0008 (8)	−0.0038 (9)
C6	0.0572 (13)	0.0703 (14)	0.0429 (11)	0.0126 (11)	0.0061 (9)	−0.0134 (10)
C7	0.0612 (12)	0.0685 (14)	0.0318 (9)	−0.0020 (11)	0.0013 (9)	−0.0094 (9)
O1	0.0487 (9)	0.0727 (11)	0.0889 (12)	0.0073 (8)	0.0163 (8)	−0.0161 (9)
O2	0.0548 (9)	0.0635 (10)	0.0598 (9)	−0.0069 (7)	0.0087 (7)	−0.0173 (8)
O3	0.0395 (8)	0.0752 (10)	0.0628 (10)	−0.0077 (7)	−0.0046 (6)	−0.0065 (7)
N3	0.0440 (9)	0.0596 (11)	0.0310 (8)	−0.0007 (8)	−0.0012 (6)	0.0000 (7)

N1—C1	1.102 (3)	C4—C5	1.361 (3)
N2—C4	1.469 (2)	C5—C6	1.389 (3)
N2—H2A	0.89	C5—H5	0.93
N2—H2B	0.89	C6—C7	1.335 (3)
N2—H2C	0.89	C6—H6	0.93
C1—C2	1.397 (3)	C7—H7	0.93
C2—C7	1.374 (3)	O1—N3	1.211 (2)
C2—C3	1.402 (3)	O2—N3	1.309 (2)
C3—C4	1.335 (2)	O3—N3	1.196 (2)
C3—H3	0.93
C4—N2—H2A	109.5	C3—C4—N2	118.82 (15)
C4—N2—H2B	109.5	C5—C4—N2	120.72 (16)
H2A—N2—H2B	109.5	C4—C5—C6	121.42 (18)
C4—N2—H2C	109.5	C4—C5—H5	119.3
H2A—N2—H2C	109.5	C6—C5—H5	119.3
H2B—N2—H2C	109.5	C7—C6—C5	119.66 (19)
N1—C1—C2	178.6 (2)	C7—C6—H6	120.2
C7—C2—C1	117.84 (17)	C5—C6—H6	120.2
C7—C2—C3	122.50 (17)	C6—C7—C2	118.37 (17)
C1—C2—C3	119.66 (17)	C6—C7—H7	120.8
C4—C3—C2	117.60 (17)	C2—C7—H7	120.8
C4—C3—H3	121.2	O3—N3—O1	115.22 (17)
C2—C3—H3	121.2	O3—N3—O2	121.07 (16)
C3—C4—C5	120.45 (17)	O1—N3—O2	123.69 (16)

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

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

Symmetry codes: (i) ; (ii) .