2-Amino-5-cyano-pyridinium nitrate.

In the title compound, C(6)H(6)N(3) (+)·NO(3) (-), the packing is consolidatedby N-H⋯N and N-H⋯O hydrogen bonds.

Related literature

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

Experimental

Crystal data

C6H6N3 +·NO3 −

M = 182.15

Monoclinic,

a = 4.6475 (9) Å

b = 12.713 (3) Å

c = 13.417 (3) Å

β = 97.91 (3)°

V = 785.1 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.13 mm−1

T = 298 (2) K

0.25 × 0.15 × 0.15 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.975, T max = 0.981

8053 measured reflections

1798 independent reflections

1163 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.127

S = 1.07

1798 reflections

142 parameters

All H-atom parameters refined

Δρmax = 0.17 e Å−3

Δρmin = −0.17 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/S1600536808028031/wk2092sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808028031/wk2092Isup2.hkl

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

C6H6N3+·NO3−	F(000) = 376
Mr = 182.15	Dx = 1.541 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1796 reflections
a = 4.6475 (9) Å	θ = 3.1–27.5°
b = 12.713 (3) Å	µ = 0.13 mm−1
c = 13.417 (3) Å	T = 298 K
β = 97.91 (3)°	Block, colourless
V = 785.1 (3) Å3	0.25 × 0.15 × 0.15 mm
Z = 4

Rigaku Mercury2 diffractometer	1798 independent reflections
Radiation source: fine-focus sealed tube	1163 reflections with I > 2σ(I)
graphite	Rint = 0.050
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.1°
ω scans	h = −6→6
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −16→16
Tmin = 0.975, Tmax = 0.981	l = −17→17
8053 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)] = 0.053	Hydrogen site location: difference Fourier map
wR(F2) = 0.127	All H-atom parameters refined
S = 1.07	w = 1/[σ2(Fo2) + (0.0514P)2 + 0.1542P] where P = (Fo2 + 2Fc2)/3
1798 reflections	(Δ/σ)max < 0.001
142 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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
C2	0.7591 (5)	0.86151 (17)	0.31844 (17)	0.0428 (5)
N4	0.0550 (4)	0.94943 (14)	0.12683 (14)	0.0456 (5)
N2	0.4566 (4)	0.71680 (19)	0.25422 (16)	0.0509 (5)
O1	−0.1866 (3)	0.98288 (12)	0.08728 (13)	0.0604 (5)
O2	0.2162 (4)	1.00628 (14)	0.18518 (14)	0.0651 (5)
O3	0.1266 (4)	0.85819 (13)	0.10891 (13)	0.0610 (5)
N1	0.8152 (4)	0.69031 (15)	0.38842 (14)	0.0406 (4)
C3	0.9809 (5)	0.89511 (17)	0.38692 (17)	0.0435 (5)
C5	1.0356 (4)	0.72284 (18)	0.45750 (17)	0.0402 (5)
C6	1.3541 (5)	0.86115 (17)	0.53382 (18)	0.0476 (6)
C1	0.6718 (4)	0.75525 (16)	0.31857 (15)	0.0379 (5)
C4	1.1235 (4)	0.82498 (16)	0.45893 (16)	0.0388 (5)
N3	1.5342 (5)	0.89264 (16)	0.59161 (18)	0.0684 (7)
H5	1.126 (4)	0.6708 (16)	0.5011 (15)	0.036 (5)*
H2A	0.655 (4)	0.9049 (16)	0.2716 (15)	0.033 (5)*
H3	1.041 (4)	0.9695 (19)	0.3867 (16)	0.051 (6)*
H2B	0.401 (5)	0.650 (2)	0.2641 (17)	0.048 (7)*
H1	0.764 (5)	0.620 (2)	0.389 (2)	0.067 (8)*
H2C	0.370 (6)	0.761 (3)	0.216 (2)	0.082 (10)*

	U11	U22	U33	U12	U13	U23
C2	0.0473 (13)	0.0351 (11)	0.0432 (12)	0.0020 (9)	−0.0043 (11)	0.0098 (10)
N4	0.0556 (12)	0.0365 (10)	0.0425 (10)	0.0046 (9)	−0.0013 (9)	0.0013 (9)
N2	0.0512 (12)	0.0424 (12)	0.0529 (12)	−0.0048 (10)	−0.0146 (10)	0.0011 (10)
O1	0.0532 (10)	0.0445 (9)	0.0766 (12)	0.0102 (8)	−0.0156 (9)	−0.0064 (8)
O2	0.0615 (11)	0.0566 (11)	0.0698 (11)	0.0031 (8)	−0.0179 (9)	−0.0180 (9)
O3	0.0770 (12)	0.0405 (9)	0.0599 (11)	0.0171 (8)	−0.0098 (9)	−0.0044 (8)
N1	0.0405 (10)	0.0306 (10)	0.0478 (11)	−0.0032 (8)	−0.0041 (8)	0.0032 (8)
C3	0.0471 (13)	0.0323 (12)	0.0492 (13)	−0.0021 (10)	−0.0003 (11)	0.0029 (10)
C5	0.0394 (11)	0.0383 (12)	0.0408 (12)	0.0034 (9)	−0.0025 (10)	0.0052 (10)
C6	0.0495 (14)	0.0373 (12)	0.0515 (14)	−0.0002 (10)	−0.0089 (12)	0.0008 (10)
C1	0.0356 (11)	0.0399 (12)	0.0370 (11)	0.0027 (9)	0.0007 (9)	0.0003 (9)
C4	0.0355 (11)	0.0377 (12)	0.0414 (11)	−0.0002 (9)	−0.0014 (9)	0.0020 (10)
N3	0.0697 (14)	0.0501 (13)	0.0755 (16)	−0.0045 (11)	−0.0249 (13)	−0.0036 (11)

C2—C3	1.352 (3)	N1—C5	1.348 (3)
C2—C1	1.411 (3)	N1—C1	1.354 (3)
C2—H2A	0.92 (2)	N1—H1	0.92 (3)
N4—O3	1.239 (2)	C3—C4	1.411 (3)
N4—O2	1.239 (2)	C3—H3	0.99 (2)
N4—O1	1.249 (2)	C5—C4	1.361 (3)
N2—C1	1.322 (3)	C5—H5	0.94 (2)
N2—H2B	0.90 (2)	C6—N3	1.133 (3)
N2—H2C	0.83 (3)	C6—C4	1.440 (3)
C3—C2—C1	119.6 (2)	C2—C3—H3	119.4 (13)
C3—C2—H2A	123.7 (12)	C4—C3—H3	120.0 (13)
C1—C2—H2A	116.7 (12)	N1—C5—C4	120.1 (2)
O3—N4—O2	120.89 (19)	N1—C5—H5	116.3 (12)
O3—N4—O1	119.08 (18)	C4—C5—H5	123.6 (12)
O2—N4—O1	120.00 (18)	N3—C6—C4	177.9 (2)
C1—N2—H2B	117.2 (15)	N2—C1—N1	118.9 (2)
C1—N2—H2C	115 (2)	N2—C1—C2	123.1 (2)
H2B—N2—H2C	127 (3)	N1—C1—C2	118.07 (19)
C5—N1—C1	123.0 (2)	C5—C4—C3	118.77 (19)
C5—N1—H1	117.7 (16)	C5—C4—C6	120.53 (19)
C1—N1—H1	119.4 (17)	C3—C4—C6	120.69 (19)
C2—C3—C4	120.5 (2)
C1—C2—C3—C4	−0.6 (3)	C3—C2—C1—N1	0.2 (3)
C1—N1—C5—C4	−0.2 (3)	N1—C5—C4—C3	−0.3 (3)
C5—N1—C1—N2	−179.4 (2)	N1—C5—C4—C6	178.5 (2)
C5—N1—C1—C2	0.2 (3)	C2—C3—C4—C5	0.6 (3)
C3—C2—C1—N2	179.8 (2)	C2—C3—C4—C6	−178.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O2i	0.90 (2)	2.05 (3)	2.941 (3)	169 (2)
N1—H1···O1i	0.92 (3)	1.82 (3)	2.733 (2)	170 (2)
N1—H1···N4i	0.92 (3)	2.62 (3)	3.505 (3)	161 (2)
N2—H2C···O3	0.83 (3)	2.10 (3)	2.926 (3)	174 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯O2i	0.90 (2)	2.05 (3)	2.941 (3)	169 (2)
N1—H1⋯O1i	0.92 (3)	1.82 (3)	2.733 (2)	170 (2)
N2—H2C⋯O3	0.83 (3)	2.10 (3)	2.926 (3)	174 (3)

Symmetry code: (i) .