4-Cyano-pyridinium nitrate.

The title compound, C(6)H(5)N(2) (+)·NO(3) (-), is a proton-transfer compound between 4-cyano-pyridine and nitric acid. In the asymmetric unit, the components are linked by a strong N-H⋯O hydrogen bond. In the crystal, mol-ecules are linked into a C(6) chain along [010] by C-H⋯O inter-actions.

Related literature

For the structures and ferroelectric properties of related compounds, see: Fu et al. (2011a ▶,b ▶,c ▶); Dai & Chen (2011 ▶); Xu et al. (2011 ▶); Zheng (2011 ▶). For graph-set motif see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C6H5N2 +·NO3 −

M = 167.13

Monoclinic,

a = 6.3663 (2) Å

b = 13.2868 (9) Å

c = 9.1019 (2) Å

β = 103.755 (1)°

V = 747.83 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 298 K

0.10 × 0.05 × 0.05 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.910, T max = 1.000

5151 measured reflections

1694 independent reflections

1349 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.146

S = 1.14

1694 reflections

109 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.23 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: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812020697/bx2407sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812020697/bx2407Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812020697/bx2407Isup3.cml

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

C6H5N2+·NO3−	F(000) = 344
Mr = 167.13	Dx = 1.484 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1694 reflections
a = 6.3663 (2) Å	θ = 2.8–27.5°
b = 13.2868 (9) Å	µ = 0.12 mm−1
c = 9.1019 (2) Å	T = 298 K
β = 103.755 (1)°	Block, colourless
V = 747.83 (6) Å3	0.10 × 0.05 × 0.05 mm
Z = 4

Rigaku Mercury2 diffractometer	1694 independent reflections
Radiation source: fine-focus sealed tube	1349 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 2.8°
CCD profile fitting scans	h = −8→7
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −17→15
Tmin = 0.910, Tmax = 1.000	l = −11→11
5151 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146	H-atom parameters constrained
S = 1.14	w = 1/[σ2(Fo2) + (0.0719P)2 + 0.0927P] where P = (Fo2 + 2Fc2)/3
1694 reflections	(Δ/σ)max < 0.001
109 parameters	Δρmax = 0.23 e Å−3
1 restraint	Δρmin = −0.19 e Å−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
O3	0.7551 (2)	0.46541 (8)	0.20815 (14)	0.0477 (4)
N3	0.7428 (2)	0.42233 (11)	0.08092 (16)	0.0447 (4)
N1	0.7453 (2)	0.66359 (10)	0.17652 (16)	0.0440 (4)
H1	0.7413	0.5962	0.1860	0.053*
C3	0.7627 (3)	0.86509 (12)	0.13720 (18)	0.0400 (4)
N2	0.7637 (3)	1.05763 (13)	0.0946 (2)	0.0648 (5)
C4	0.6008 (3)	0.82380 (12)	0.1963 (2)	0.0456 (4)
H4A	0.4974	0.8648	0.2230	0.055*
O2	0.7350 (2)	0.32899 (10)	0.07536 (16)	0.0631 (4)
C2	0.9185 (3)	0.80337 (13)	0.0992 (2)	0.0455 (4)
H2A	1.0287	0.8304	0.0603	0.055*
C5	0.5955 (3)	0.72140 (13)	0.2149 (2)	0.0466 (4)
H5A	0.4877	0.6924	0.2543	0.056*
O1	0.7392 (3)	0.47362 (11)	−0.03265 (17)	0.0684 (5)
C1	0.9049 (3)	0.70149 (13)	0.1208 (2)	0.0474 (4)
H1A	1.0073	0.6587	0.0966	0.057*
C6	0.7672 (3)	0.97304 (14)	0.1142 (2)	0.0484 (5)

	U11	U22	U33	U12	U13	U23
O3	0.0566 (8)	0.0384 (6)	0.0478 (7)	−0.0022 (5)	0.0118 (6)	−0.0026 (5)
N3	0.0376 (8)	0.0469 (8)	0.0511 (9)	0.0017 (6)	0.0136 (6)	−0.0006 (6)
N1	0.0483 (8)	0.0339 (7)	0.0491 (8)	−0.0012 (6)	0.0102 (6)	0.0000 (6)
C3	0.0417 (9)	0.0359 (8)	0.0399 (8)	−0.0008 (6)	0.0047 (6)	0.0005 (6)
N2	0.0756 (13)	0.0408 (9)	0.0743 (12)	−0.0017 (8)	0.0107 (10)	0.0084 (7)
C4	0.0448 (9)	0.0431 (9)	0.0513 (10)	0.0059 (7)	0.0165 (8)	0.0003 (7)
O2	0.0760 (10)	0.0423 (8)	0.0727 (10)	−0.0014 (6)	0.0211 (8)	−0.0115 (6)
C2	0.0419 (9)	0.0464 (9)	0.0506 (10)	−0.0030 (7)	0.0157 (7)	0.0009 (7)
C5	0.0448 (10)	0.0457 (10)	0.0513 (10)	−0.0031 (8)	0.0153 (8)	0.0032 (7)
O1	0.0877 (11)	0.0705 (10)	0.0542 (8)	0.0080 (8)	0.0313 (7)	0.0124 (7)
C1	0.0466 (10)	0.0447 (9)	0.0527 (10)	0.0046 (8)	0.0155 (8)	−0.0042 (7)
C6	0.0504 (11)	0.0429 (10)	0.0495 (9)	−0.0015 (7)	0.0071 (8)	0.0018 (7)

O3—N3	1.2774 (18)	C3—C6	1.451 (2)
N3—O1	1.234 (2)	N2—C6	1.137 (2)
N3—O2	1.2418 (19)	C4—C5	1.373 (2)
N1—C5	1.334 (2)	C4—H4A	0.9300
N1—C1	1.337 (2)	C2—C1	1.374 (2)
N1—H1	0.9005	C2—H2A	0.9300
C3—C4	1.385 (2)	C5—H5A	0.9300
C3—C2	1.392 (2)	C1—H1A	0.9300
O1—N3—O2	121.67 (16)	C3—C4—H4A	120.6
O1—N3—O3	119.80 (15)	C1—C2—C3	118.17 (15)
O2—N3—O3	118.53 (14)	C1—C2—H2A	120.9
C5—N1—C1	122.52 (15)	C3—C2—H2A	120.9
C5—N1—H1	120.6	N1—C5—C4	119.88 (16)
C1—N1—H1	116.9	N1—C5—H5A	120.1
C4—C3—C2	120.22 (15)	C4—C5—H5A	120.1
C4—C3—C6	119.33 (15)	N1—C1—C2	120.31 (16)
C2—C3—C6	120.44 (15)	N1—C1—H1A	119.8
C5—C4—C3	118.89 (15)	C2—C1—H1A	119.8
C5—C4—H4A	120.6	N2—C6—C3	177.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3	0.90	1.75	2.6481 (18)	176
C4—H4A···O3i	0.93	2.29	3.220 (2)	179

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3	0.90	1.75	2.6481 (18)	176
C4—H4A⋯O3i	0.93	2.29	3.220 (2)	179

Symmetry code: (i) .