4-Amino­pyridinium nitrate

The structure of the organic–inorganic hybrid material 4-amino­pyridinium nitrate, C₅H₇N₂⁺·NO₃⁻, exhibits classical and bifurcated strong N—H...O hydrogen-bonding inter­actions, as well as weaker C—H...O inter­actions. Organic 4-amino­pyridinium cations and inorganic nitrate anions inter­act to form a one-dimensional hydrogen-bonded ribbon in the a direction. Neighbouring ribbons inter­act to form two-dimensional corrugated hydrogen-bonded sheets parallel to the ac plane.

Key indicators

• Single-crystal X-ray study
• T = 200 K
• Mean [sigma](Wave) = 0.000 Å
• R factor = 0.048
• wR factor = 0.116
• Data-to-parameter ratio = 20.6

checkCIF/PLATON results

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Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2003); program(s) used to solve structure: SHELXL97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2003).

4-Aminopyridinium nitrate

Crystal data

C5H7N2^+·NO3^−	F(000) = 328
Mr = 157.14	Dx = 1.496 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 209 reflections
a = 9.192 (4) Å	θ = 2–30°
b = 6.996 (4) Å	µ = 0.13 mm^−1
c = 10.869 (5) Å	T = 200 K
β = 93.60 (4)°	Needle, colourless
V = 697.5 (6) Å^3	0.20 × 0.20 × 0.20 mm
Z = 4

Data collection

Oxford Excalibur2 diffractometer	1369 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.036
Graphite monochromator	θmax = 31.8°, θmin = 4.2°
ω/2θ scans	h = −13→13
6090 measured reflections	k = −10→8
2220 independent reflections	l = −16→15

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 0.94	w = 1/[σ^2(Fo^2) + (0.0545P)^2] where P = (Fo^2 + 2Fc^2)/3
2220 reflections	(Δ/σ)max = 0.002
108 parameters	Δρmax = 0.22 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
H1A	0.5501 (19)	0.193 (2)	0.9511 (17)	0.054 (5)*
H1B	0.577 (2)	0.104 (2)	0.8252 (19)	0.062 (6)*
O1	0.77850 (11)	0.05911 (14)	0.74230 (9)	0.0353 (3)
N1	0.51723 (13)	0.13733 (18)	0.87877 (13)	0.0331 (3)
C1	0.37418 (14)	0.12040 (16)	0.85447 (12)	0.0247 (3)
O2	0.62171 (11)	0.13015 (15)	0.59360 (10)	0.0449 (3)
N2	0.07612 (13)	0.09205 (16)	0.80423 (12)	0.0326 (3)
H2A	−0.0165	0.0849	0.7879	0.039*
N3	0.75137 (12)	0.11466 (15)	0.63267 (11)	0.0289 (3)
C5	0.27392 (14)	0.17066 (19)	0.94304 (12)	0.0281 (3)
H5	0.3079	0.2132	1.0206	0.034*
C2	0.31506 (15)	0.04882 (18)	0.74069 (12)	0.0292 (3)
H2	0.3767	0.0091	0.6810	0.035*
C4	0.12835 (15)	0.15669 (18)	0.91469 (13)	0.0322 (3)
H4	0.0636	0.1926	0.9729	0.039*
O3	0.85311 (12)	0.15115 (16)	0.56697 (9)	0.0431 (3)
C3	0.16864 (16)	0.03793 (19)	0.71823 (13)	0.0321 (3)
H3	0.1308	−0.0075	0.6424	0.039*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0318 (6)	0.0452 (6)	0.0290 (5)	0.0023 (4)	0.0024 (4)	0.0032 (4)
N1	0.0240 (6)	0.0430 (7)	0.0327 (7)	−0.0007 (5)	0.0042 (5)	0.0001 (6)
C1	0.0255 (7)	0.0217 (6)	0.0271 (7)	0.0022 (5)	0.0029 (5)	0.0042 (5)
O2	0.0286 (6)	0.0582 (7)	0.0467 (7)	−0.0011 (5)	−0.0063 (5)	0.0069 (5)
N2	0.0233 (6)	0.0341 (6)	0.0399 (7)	−0.0003 (4)	−0.0022 (5)	0.0041 (5)
N3	0.0268 (6)	0.0288 (6)	0.0310 (6)	−0.0025 (4)	0.0026 (5)	−0.0031 (5)
C5	0.0285 (7)	0.0301 (7)	0.0259 (7)	0.0019 (5)	0.0023 (5)	−0.0016 (5)
C2	0.0347 (8)	0.0265 (7)	0.0267 (7)	0.0032 (5)	0.0058 (6)	−0.0007 (5)
C4	0.0316 (8)	0.0315 (7)	0.0342 (8)	0.0063 (6)	0.0087 (6)	0.0028 (6)
O3	0.0382 (6)	0.0555 (7)	0.0369 (6)	−0.0103 (5)	0.0137 (5)	−0.0002 (5)
C3	0.0376 (8)	0.0300 (7)	0.0282 (7)	−0.0012 (6)	−0.0029 (6)	−0.0012 (6)

Geometric parameters (Å, º)

O1—N3	1.2632 (15)	N2—H2A	0.8600
N1—C1	1.3301 (18)	N3—O3	1.2383 (15)
N1—H1A	0.913 (19)	C5—C4	1.3577 (19)
N1—H1B	0.86 (2)	C5—H5	0.9300
C1—C2	1.4110 (19)	C2—C3	1.355 (2)
C1—C5	1.4181 (18)	C2—H2	0.9300
O2—N3	1.2446 (15)	C4—H4	0.9300
N2—C4	1.3431 (18)	C3—H3	0.9300
N2—C3	1.3564 (19)
C1—N1—H1A	118.6 (11)	C4—C5—C1	120.09 (13)
C1—N1—H1B	120.6 (14)	C4—C5—H5	120.0
H1A—N1—H1B	120.6 (18)	C1—C5—H5	120.0
N1—C1—C2	121.81 (13)	C3—C2—C1	120.10 (13)
N1—C1—C5	121.31 (13)	C3—C2—H2	120.0
C2—C1—C5	116.87 (12)	C1—C2—H2	120.0
C4—N2—C3	120.37 (12)	N2—C4—C5	121.27 (13)
C4—N2—H2A	119.8	N2—C4—H4	119.4
C3—N2—H2A	119.8	C5—C4—H4	119.4
O3—N3—O2	121.80 (13)	C2—C3—N2	121.25 (13)
O3—N3—O1	119.72 (12)	C2—C3—H3	119.4
O2—N3—O1	118.48 (12)	N2—C3—H3	119.4
N1—C1—C5—C4	178.28 (13)	C3—N2—C4—C5	0.37 (19)
C2—C1—C5—C4	−2.77 (18)	C1—C5—C4—N2	1.3 (2)
N1—C1—C2—C3	−178.43 (13)	C1—C2—C3—N2	−1.1 (2)
C5—C1—C2—C3	2.63 (18)	C4—N2—C3—C2	−0.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O2	0.86 (2)	2.58 (2)	3.302 (2)	142.5 (17)
N1—H1B···O1	0.86 (2)	2.14 (2)	2.952 (2)	159.3 (19)
N2—H2A···O1^i	0.88 (2)	1.90 (2)	2.784 (2)	175 (2)
N2—H2A···O3^i	0.88 (2)	2.66 (2)	3.218 (2)	122 (2)
N2—H2A···N3^i	0.88 (2)	2.63 (2)	3.421 (2)	149 (2)

Symmetry code: (i) x−1, y, z.