(2-Pyridyl­methyl)­ammonium nitrate

The single-crystal structure of (2-pyridyl­methyl)­ammonium nitrate, C₆H₉N₂⁺·NO₃^-, is presented, in what is only the third reported structure containing this cation. The structure contains extensively hydrogen-bonded layers.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.043
• wR factor = 0.097
• Data-to-parameter ratio = 15.0

checkCIF/PLATON results

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Computing details

Data collection: COLLECT (Nonius, 1998); cell refinement: DIRAX (Duisenberg, 1992); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SHELXS6 (Sheldrick, 1985); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

(I)

Crystal data

C6H9N2^+·NO3^−	F(000) = 360
Mr = 171.16	Dx = 1.463 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 59 reflections
a = 8.2492 (4) Å	θ = 5.5–20.8°
b = 10.4014 (5) Å	µ = 0.12 mm^−1
c = 9.3850 (5) Å	T = 150 K
β = 105.171 (4)°	Block, colourless
V = 777.20 (7) Å^3	0.2 × 0.1 × 0.1 mm
Z = 4

Data collection

Nonius KappaCCD diffractometer	1228 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.057
Graphite monochromator	θmax = 27.4°, θmin = 2.6°
φ and ω scans	h = −10→10
18148 measured reflections	k = −13→13
1774 independent reflections	l = −12→12

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.043	Hydrogen site location: mixed
wR(F^2) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0364P)^2 + 0.3509P] where P = (Fo^2 + 2Fc^2)/3
1774 reflections	(Δ/σ)max < 0.001
118 parameters	Δρmax = 0.19 e Å^−3
0 restraints	Δρmin = −0.23 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.30006 (17)	0.43664 (13)	0.09967 (14)	0.0227 (3)
N2	0.52094 (18)	0.32680 (14)	−0.02714 (16)	0.0212 (3)
H2A	0.502 (2)	0.4097 (19)	−0.073 (2)	0.032*
H2B	0.590 (2)	0.2819 (18)	−0.073 (2)	0.032*
H2C	0.578 (2)	0.3381 (17)	0.073 (2)	0.032*
C1	0.2010 (2)	0.49371 (18)	0.17383 (18)	0.0270 (4)
H1	0.2345	0.5751	0.2176	0.032*
C2	0.0542 (2)	0.44125 (18)	0.19013 (19)	0.0295 (4)
H2	−0.0119	0.4854	0.2435	0.035*
C3	0.0050 (2)	0.32320 (19)	0.12727 (19)	0.0314 (4)
H3	−0.0961	0.2844	0.1363	0.038*
C4	0.1047 (2)	0.26232 (18)	0.05104 (18)	0.0272 (4)
H4	0.0739	0.1807	0.0069	0.033*
C5	0.2507 (2)	0.32224 (16)	0.03990 (17)	0.0210 (4)
C6	0.3627 (2)	0.25603 (16)	−0.04054 (18)	0.0248 (4)
H6A	0.3888	0.1683	0.0000	0.030*
H6B	0.3025	0.2479	−0.1462	0.030*
O1	0.66629 (15)	0.31660 (11)	0.28255 (12)	0.0263 (3)
O2	0.68263 (16)	0.52342 (12)	0.26607 (14)	0.0349 (3)
O3	0.7063 (2)	0.43410 (13)	0.47739 (14)	0.0455 (4)
N3	0.68525 (17)	0.42684 (14)	0.34289 (15)	0.0249 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0275 (8)	0.0202 (7)	0.0217 (7)	0.0009 (6)	0.0089 (6)	0.0011 (6)
N2	0.0266 (8)	0.0185 (8)	0.0211 (8)	0.0002 (6)	0.0105 (6)	−0.0023 (6)
C1	0.0340 (10)	0.0246 (9)	0.0245 (9)	0.0058 (8)	0.0116 (7)	0.0019 (7)
C2	0.0279 (10)	0.0372 (11)	0.0264 (9)	0.0110 (8)	0.0124 (8)	0.0062 (8)
C3	0.0206 (9)	0.0426 (11)	0.0311 (10)	−0.0001 (8)	0.0072 (7)	0.0095 (9)
C4	0.0253 (9)	0.0281 (10)	0.0260 (9)	−0.0034 (8)	0.0028 (7)	0.0020 (8)
C5	0.0238 (8)	0.0205 (8)	0.0178 (8)	0.0020 (7)	0.0036 (6)	0.0038 (7)
C6	0.0291 (9)	0.0205 (9)	0.0264 (9)	−0.0036 (7)	0.0103 (7)	−0.0029 (7)
O1	0.0348 (7)	0.0205 (6)	0.0253 (6)	−0.0015 (5)	0.0110 (5)	−0.0025 (5)
O2	0.0394 (8)	0.0256 (7)	0.0358 (7)	−0.0061 (6)	0.0031 (6)	0.0124 (6)
O3	0.0800 (11)	0.0351 (8)	0.0205 (7)	−0.0064 (7)	0.0118 (7)	−0.0032 (6)
N3	0.0243 (8)	0.0248 (8)	0.0253 (8)	−0.0015 (6)	0.0061 (6)	0.0029 (7)

Geometric parameters (Å, º)

N1—C5	1.333 (2)	C3—C4	1.378 (2)
N1—C1	1.342 (2)	C3—H3	0.9500
N2—C6	1.475 (2)	C4—C5	1.384 (2)
N2—H2A	0.96 (2)	C4—H4	0.9500
N2—H2B	0.93 (2)	C5—C6	1.505 (2)
N2—H2C	0.94 (2)	C6—H6A	0.9900
C1—C2	1.373 (2)	C6—H6B	0.9900
C1—H1	0.9500	O1—N3	1.2703 (18)
C2—C3	1.377 (3)	O2—N3	1.2334 (17)
C2—H2	0.9500	O3—N3	1.2307 (18)
C5—N1—C1	116.90 (15)	C3—C4—C5	118.82 (17)
C6—N2—H2A	111.9 (11)	C3—C4—H4	120.6
C6—N2—H2B	110.3 (11)	C5—C4—H4	120.6
H2A—N2—H2B	107.1 (15)	N1—C5—C4	123.12 (15)
C6—N2—H2C	110.6 (11)	N1—C5—C6	117.35 (14)
H2A—N2—H2C	108.5 (16)	C4—C5—C6	119.52 (15)
H2B—N2—H2C	108.4 (16)	N2—C6—C5	112.02 (14)
N1—C1—C2	123.81 (17)	N2—C6—H6A	109.2
N1—C1—H1	118.1	C5—C6—H6A	109.2
C2—C1—H1	118.1	N2—C6—H6B	109.2
C1—C2—C3	118.46 (16)	C5—C6—H6B	109.2
C1—C2—H2	120.8	H6A—C6—H6B	107.9
C3—C2—H2	120.8	O3—N3—O2	121.72 (15)
C2—C3—C4	118.90 (17)	O3—N3—O1	118.72 (14)
C2—C3—H3	120.6	O2—N3—O1	119.56 (13)
C4—C3—H3	120.6

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2^i	0.958 (19)	2.155 (18)	2.8817 (19)	131.7 (15)
N2—H2A···N1^i	0.958 (19)	2.345 (18)	3.037 (2)	128.7 (13)
N2—H2B···O1^ii	0.925 (18)	1.931 (18)	2.8237 (19)	161.4 (16)
N2—H2B···O3^ii	0.925 (18)	2.440 (19)	3.110 (2)	129.3 (15)
N2—H2C···O1	0.942 (18)	1.923 (18)	2.8412 (18)	164.3 (16)

Symmetry codes: (i) −x+1, −y+1, −z; (ii) x, −y+1/2, z−1/2.