2-Amino-5-methyl-pyridinium nitrate.

In the title salt, C(6)H(9)N(2) (+)·NO(3) (-), the 2-amino-5-methyl-pyridinium cation and the nitrate anion are cyclically linked through pyridinium and amine N-H⋯O hydrogen bonds [graph set R(4) (3)(12)]. These units are extended into a zigzag chain structure lying parallel to the a axis, through a second cyclic R(2) (2)(8) association involving amine N-H⋯O and aromatic C-H⋯O hydrogen bonds to nitrate O-atom acceptors.

Related literature

For supra­molecular architectures, see: Wang et al. (2012 ▶). For the potential of amine derivatives to form metal-organic frameworks, see: Manzur et al. (2007 ▶); Ismayilov et al. (2007 ▶); Austria et al. (2007 ▶). For related structures, see: Nahringbauer & Kvick (1977 ▶); Sherfinski & Marsh (1975 ▶); Zaouali Zgolli et al. (2009 ▶); Dai (2008 ▶). For graph-set analysis, see: Etter et al. (1990 ▶).

Experimental

Crystal data

C6H9N2 +·NO3 −

M = 171.16

Monoclinic,

a = 8.7711 (7) Å

b = 15.7261 (13) Å

c = 6.8539 (5) Å

β = 117.455 (2)°

V = 838.92 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 298 K

0.49 × 0.38 × 0.21 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.948, T max = 0.977

2040 measured reflections

1251 independent reflections

1077 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.109

S = 1.08

1251 reflections

111 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.13 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; 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 datablock(s) I, global. DOI: 10.1107/S1600536812025196/zs2211sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812025196/zs2211Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812025196/zs2211Isup3.cml

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

C6H9N2+·NO3−	F(000) = 360
Mr = 171.16	Dx = 1.355 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 1097 reflections
a = 8.7711 (7) Å	θ = 2.6–25.8°
b = 15.7261 (13) Å	µ = 0.11 mm−1
c = 6.8539 (5) Å	T = 298 K
β = 117.455 (2)°	Needle, light-yellow
V = 838.92 (12) Å3	0.49 × 0.38 × 0.21 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	1251 independent reflections
Radiation source: fine-focus sealed tube	1077 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
φ and ω scans	θmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.948, Tmax = 0.977	k = −15→18
2040 measured reflections	l = −8→8

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)] = 0.039	H-atom parameters constrained
wR(F2) = 0.109	w = 1/[σ2(Fo2) + (0.0569P)2 + 0.1897P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
1251 reflections	Δρmax = 0.15 e Å−3
111 parameters	Δρmin = −0.13 e Å−3
2 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.010 (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
N1	0.3088 (3)	0.46545 (15)	0.4791 (4)	0.0474 (6)
H1	0.2362	0.4246	0.4239	0.057*
N2	0.5229 (4)	0.36493 (16)	0.6464 (4)	0.0593 (7)
H2A	0.4482	0.3251	0.5882	0.071*
H2B	0.6289	0.3524	0.7293	0.071*
N3	0.4592 (3)	0.14462 (15)	0.6312 (5)	0.0583 (7)
O1	0.3527 (3)	0.19547 (15)	0.5007 (4)	0.0897 (9)
O2	0.5816 (3)	0.17188 (14)	0.8011 (5)	0.0823 (8)
O3	0.4431 (3)	0.06826 (15)	0.5931 (5)	0.0912 (9)
C1	0.4743 (3)	0.44596 (15)	0.6084 (4)	0.0450 (7)
C2	0.5894 (4)	0.51441 (18)	0.6972 (5)	0.0499 (7)
H2	0.7054	0.5042	0.7882	0.060*
C3	0.5302 (4)	0.59519 (18)	0.6493 (5)	0.0534 (8)
H3	0.6077	0.6399	0.7078	0.064*
C4	0.3574 (4)	0.61376 (17)	0.5153 (5)	0.0507 (7)
C5	0.2500 (4)	0.54681 (17)	0.4312 (5)	0.0519 (7)
H5	0.1340	0.5565	0.3390	0.062*
C6	0.2926 (5)	0.7045 (2)	0.4632 (7)	0.0767 (11)
H6A	0.1721	0.7042	0.3623	0.115*
H6B	0.3539	0.7339	0.3982	0.115*
H6C	0.3109	0.7328	0.5963	0.115*

	U11	U22	U33	U12	U13	U23
N1	0.0453 (13)	0.0430 (12)	0.0475 (15)	−0.0055 (9)	0.0158 (11)	−0.0011 (9)
N2	0.0636 (15)	0.0432 (13)	0.0635 (17)	0.0047 (11)	0.0229 (14)	0.0007 (11)
N3	0.0418 (12)	0.0480 (14)	0.0724 (17)	0.0017 (11)	0.0154 (13)	−0.0003 (13)
O1	0.0638 (16)	0.0579 (14)	0.094 (2)	0.0036 (12)	−0.0086 (14)	0.0108 (13)
O2	0.0610 (14)	0.0595 (14)	0.0835 (17)	0.0097 (11)	−0.0034 (14)	−0.0153 (12)
O3	0.0633 (15)	0.0508 (13)	0.120 (2)	0.0005 (11)	0.0085 (16)	−0.0118 (13)
C1	0.0483 (17)	0.0421 (14)	0.0417 (17)	−0.0008 (12)	0.0183 (13)	−0.0006 (12)
C2	0.0452 (14)	0.0516 (16)	0.0454 (17)	−0.0025 (13)	0.0146 (14)	−0.0027 (13)
C3	0.0578 (17)	0.0450 (15)	0.058 (2)	−0.0104 (12)	0.0268 (16)	−0.0094 (12)
C4	0.063 (2)	0.0416 (15)	0.0499 (18)	0.0049 (13)	0.0278 (16)	0.0012 (13)
C5	0.0469 (16)	0.0508 (15)	0.0534 (19)	0.0053 (13)	0.0190 (14)	0.0059 (12)
C6	0.090 (3)	0.0451 (16)	0.098 (3)	0.0128 (16)	0.046 (2)	0.0119 (17)

N1—C1	1.342 (4)	C2—C3	1.354 (4)
N1—C5	1.362 (4)	C2—H2	0.9300
N1—H1	0.8600	C3—C4	1.394 (4)
N2—C1	1.331 (4)	C3—H3	0.9300
N2—H2A	0.8600	C4—C5	1.351 (4)
N2—H2B	0.8600	C4—C6	1.516 (4)
N3—O3	1.223 (3)	C5—H5	0.9300
N3—O2	1.241 (3)	C6—H6A	0.9600
N3—O1	1.241 (3)	C6—H6B	0.9600
C1—C2	1.408 (4)	C6—H6C	0.9600
C1—N1—C5	123.2 (2)	C2—C3—C4	122.3 (3)
C1—N1—H1	118.4	C2—C3—H3	118.8
C5—N1—H1	118.4	C4—C3—H3	118.8
C1—N2—H2A	120.0	C5—C4—C3	116.7 (2)
C1—N2—H2B	120.0	C5—C4—C6	121.4 (3)
H2A—N2—H2B	120.0	C3—C4—C6	121.8 (3)
O3—N3—O2	120.3 (3)	C4—C5—N1	121.2 (3)
O3—N3—O1	120.3 (3)	C4—C5—H5	119.4
O2—N3—O1	119.4 (2)	N1—C5—H5	119.4
N2—C1—N1	119.9 (3)	C4—C6—H6A	109.5
N2—C1—C2	123.1 (3)	C4—C6—H6B	109.5
N1—C1—C2	116.9 (2)	H6A—C6—H6B	109.5
C3—C2—C1	119.6 (3)	C4—C6—H6C	109.5
C3—C2—H2	120.2	H6A—C6—H6C	109.5
C1—C2—H2	120.2	H6B—C6—H6C	109.5
C5—N1—C1—N2	−179.3 (3)	C2—C3—C4—C5	−1.0 (4)
C5—N1—C1—C2	0.4 (4)	C2—C3—C4—C6	179.9 (3)
N2—C1—C2—C3	179.5 (3)	C3—C4—C5—N1	1.1 (4)
N1—C1—C2—C3	−0.2 (4)	C6—C4—C5—N1	−179.8 (3)
C1—C2—C3—C4	0.6 (4)	C1—N1—C5—C4	−0.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.86	1.95	2.808 (4)	177
N1—H1···O3i	0.86	2.53	3.122 (4)	127
N2—H2A···O1	0.86	2.18	2.992 (4)	157
N2—H2B···O1ii	0.86	2.12	2.948 (4)	160
C2—H2···O3ii	0.93	2.45	3.304 (4)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.86	1.95	2.808 (4)	177
N2—H2A⋯O1	0.86	2.18	2.992 (4)	157
N2—H2B⋯O1ii	0.86	2.12	2.948 (4)	160
C2—H2⋯O3ii	0.93	2.45	3.304 (4)	153

Symmetry codes: (i) ; (ii) .