2-Cyano-anilinium nitrate.

In the title compound, C(7)H(7)N(2) (+)·NO(3) (-), all atoms of the cation, with the exception of two H atoms of the NH(3) group, lie on a mirror plane, while the anion lies across this plane with the N and one O atom on the mirror plane. In the crystal structure, the organic cations and NO(3) (-) anions are linked by N-H⋯N and N-H⋯O hydrogen bonds, forming a two-dimensional network parallel to (100).

Related literature

For the use of amino derivatives in coordination chemisty, see: Manzur et al. (2007 ▶); Ismayilov et al. (2007 ▶); Austria et al. (2007 ▶); Wen et al. (2008 ▶).

Experimental

Crystal data

C7H7N2 +·NO3 −

M = 181.16

Orthorhombic,

a = 16.373 (3) Å

b = 6.5627 (13) Å

c = 7.9948 (16) Å

V = 859.0 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 298 (2) K

0.25 × 0.25 × 0.15 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear, Rigaku, 2005 ▶) T min = 0.927, T max = 0.983

8381 measured reflections

1072 independent reflections

797 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 0.167

S = 1.12

1072 reflections

83 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.18 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/S1600536808023313/ci2636sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808023313/ci2636Isup2.hkl

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

C7H7N2+·NO3–	F000 = 376
Mr = 181.16	Dx = 1.401 Mg m−3
Orthorhombic, Pnma	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 1592 reflections
a = 16.373 (3) Å	θ = 2.5–27.4º
b = 6.5627 (13) Å	µ = 0.11 mm−1
c = 7.9948 (16) Å	T = 298 (2) K
V = 859.0 (3) Å3	Block, colourless
Z = 4	0.25 × 0.25 × 0.15 mm

Rigaku Mercury2 diffractometer	1072 independent reflections
Radiation source: fine-focus sealed tube	797 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.041
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5º
T = 298(2) K	θmin = 2.5º
ω scans	h = −20→21
Absorption correction: multi-scan(CrystalClear, Rigaku, 2005)	k = −8→8
Tmin = 0.927, Tmax = 0.983	l = −10→10
8381 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)] = 0.063	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.167	w = 1/[σ2(Fo2) + (0.0725P)2 + 0.211P] where P = (Fo2 + 2Fc2)/3
S = 1.12	(Δ/σ)max = 0.001
1072 reflections	Δρmax = 0.17 e Å−3
83 parameters	Δρmin = −0.18 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
O1	0.76566 (11)	0.0885 (3)	0.9282 (2)	0.0793 (6)
O2	0.82708 (18)	0.2500	0.7321 (3)	0.0951 (9)
N3	0.78679 (15)	0.2500	0.8601 (3)	0.0603 (7)
N1	0.68710 (15)	0.2500	0.2370 (3)	0.0571 (7)
N2	0.6141 (4)	0.2500	0.6492 (5)	0.1409 (19)
C1	0.5859 (3)	0.2500	0.5202 (5)	0.0962 (14)
C2	0.5501 (2)	0.2500	0.3564 (4)	0.0714 (9)
C3	0.4664 (3)	0.2500	0.3345 (9)	0.1171 (18)
H3	0.4319	0.2500	0.4269	0.141*
C4	0.4342 (2)	0.2500	0.1752 (11)	0.125 (2)
H4	0.3779	0.2500	0.1609	0.150*
C5	0.4835 (3)	0.2500	0.0394 (7)	0.0980 (14)
H5	0.4609	0.2500	−0.0673	0.118*
C6	0.5668 (2)	0.2500	0.0584 (4)	0.0690 (9)
H6	0.6008	0.2500	−0.0347	0.083*
C7	0.59927 (17)	0.2500	0.2164 (3)	0.0516 (7)
H1A	0.7034 (16)	0.132 (5)	0.298 (3)	0.083 (8)*
H1B	0.714 (3)	0.2500	0.134 (6)	0.104 (14)*

	U11	U22	U33	U12	U13	U23
O1	0.0975 (13)	0.0642 (11)	0.0763 (11)	0.0153 (9)	0.0278 (9)	0.0156 (8)
O2	0.0991 (19)	0.097 (2)	0.0893 (17)	0.000	0.0552 (15)	0.000
N3	0.0525 (14)	0.0693 (17)	0.0592 (14)	0.000	0.0098 (12)	0.000
N1	0.0533 (15)	0.0752 (18)	0.0426 (13)	0.000	0.0006 (11)	0.000
N2	0.205 (5)	0.161 (4)	0.057 (2)	0.000	0.034 (3)	0.000
C1	0.126 (4)	0.105 (3)	0.057 (2)	0.000	0.039 (2)	0.000
C2	0.074 (2)	0.068 (2)	0.072 (2)	0.000	0.0283 (18)	0.000
C3	0.067 (3)	0.125 (4)	0.159 (5)	0.000	0.047 (3)	0.000
C4	0.045 (2)	0.113 (4)	0.219 (7)	0.000	−0.008 (3)	0.000
C5	0.072 (3)	0.085 (3)	0.137 (4)	0.000	−0.040 (3)	0.000
C6	0.064 (2)	0.074 (2)	0.069 (2)	0.000	−0.0116 (16)	0.000
C7	0.0504 (15)	0.0517 (15)	0.0527 (16)	0.000	0.0010 (12)	0.000

O1—N3	1.241 (2)	C2—C7	1.378 (4)
O2—N3	1.218 (3)	C3—C4	1.378 (8)
N3—O1i	1.241 (2)	C3—H3	0.93
N1—C7	1.448 (4)	C4—C5	1.353 (8)
N1—H1A	0.95 (3)	C4—H4	0.93
N1—H1B	0.94 (5)	C5—C6	1.371 (5)
N2—C1	1.130 (6)	C5—H5	0.93
C1—C2	1.434 (6)	C6—C7	1.371 (4)
C2—C3	1.382 (6)	C6—H6	0.93
O2—N3—O1i	121.32 (12)	C5—C4—C3	120.9 (4)
O2—N3—O1	121.32 (12)	C5—C4—H4	119.5
O1i—N3—O1	117.4 (2)	C3—C4—H4	119.5
C7—N1—H1A	109.7 (16)	C4—C5—C6	120.2 (5)
C7—N1—H1B	112 (3)	C4—C5—H5	119.9
H1A—N1—H1B	109 (2)	C6—C5—H5	119.9
N2—C1—C2	179.9 (5)	C7—C6—C5	119.2 (4)
C3—C2—C7	118.5 (4)	C7—C6—H6	120.4
C3—C2—C1	121.4 (4)	C5—C6—H6	120.4
C7—C2—C1	120.2 (3)	C6—C7—C2	121.4 (3)
C2—C3—C4	119.7 (4)	C6—C7—N1	119.4 (3)
C2—C3—H3	120.1	C2—C7—N1	119.2 (3)
C4—C3—H3	120.1
C7—C2—C3—C4	0.0	C5—C6—C7—N1	180.0
C1—C2—C3—C4	180.0	C3—C2—C7—C6	0.0
C2—C3—C4—C5	0.0	C1—C2—C7—C6	180.0
C3—C4—C5—C6	0.0	C3—C2—C7—N1	180.0
C4—C5—C6—C7	0.0	C1—C2—C7—N1	0.0
C5—C6—C7—C2	0.0

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ii	0.95 (3)	1.86 (3)	2.805 (2)	177 (2)
N1—H1A···N3ii	0.95 (3)	2.56 (3)	3.4523 (13)	156 (2)
N1—H1A···O2ii	0.95 (3)	2.61 (3)	3.2898 (7)	129 (2)
N1—H1B···O1iii	0.94 (5)	2.13 (4)	2.979 (3)	150 (1)
N1—H1B···O1iv	0.94 (5)	2.13 (4)	2.979 (3)	150 (1)
N1—H1B···N3iii	0.94 (5)	2.49 (5)	3.427 (4)	180 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.95 (3)	1.86 (3)	2.805 (2)	177 (2)
N1—H1A⋯N3i	0.95 (3)	2.56 (3)	3.4523 (13)	156 (2)
N1—H1A⋯O2i	0.95 (3)	2.61 (3)	3.2898 (7)	129 (2)
N1—H1B⋯O1ii	0.94 (5)	2.13 (4)	2.979 (3)	150 (1)
N1—H1B⋯O1iii	0.94 (5)	2.13 (4)	2.979 (3)	150 (1)
N1—H1B⋯N3ii	0.94 (5)	2.49 (5)	3.427 (4)	180 (3)

Symmetry codes: (i) ; (ii) ; (iii) .