4-Amino-pyridinium hydrogen succinate.

In the title salt, C(5)H(7)N(2) (+)·C(4)H(5)O(4) (-), the asymmetric unit comprises an amino-pyridinium cation and a hydrogen succinate anion as protonation of the aromatic N atom of the 4-amino-pyridine mol-ecule has occurred. The crystal packing is stabilized by inter-molecular O-H⋯O and N-H⋯O hydrogen bonds that lead to a two-dimensional array. Short C-H⋯O contacts are also present.

Related literature

For the biological activity of 4-amino­pyridine, see: Judge & Bever (2006 ▶); Schwid et al. (1997 ▶); Strupp et al. (2004 ▶). For the applications of succinic acid, see: Sauer et al. (2008 ▶); Song & Lee (2006 ▶); Zeikus et al. (1999 ▶). For related structures, see: Chao & Schempp (1977 ▶); Anderson et al. (2005 ▶); Bhattacharya et al. (1994 ▶); Karle et al. (2003 ▶); Gopalan et al. (2000 ▶); Leviel et al., (1981 ▶). For stability of the temperature controller, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C5H7N2 +·C4H5O4 −

M = 212.21

Monoclinic,

a = 6.5443 (3) Å

b = 22.2867 (11) Å

c = 7.1112 (4) Å

β = 114.587 (4)°

V = 943.13 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 100 K

0.38 × 0.14 × 0.08 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.956, T max = 0.991

7174 measured reflections

2176 independent reflections

1483 reflections with I > 2σ(I)

R int = 0.066

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.150

S = 1.06

2176 reflections

148 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.44 e Å−3

Δρmin = −0.46 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809006990/tk2378sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809006990/tk2378Isup2.hkl

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

C5H7N2+·C4H5O4−	F(000) = 448
Mr = 212.21	Dx = 1.494 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1804 reflections
a = 6.5443 (3) Å	θ = 3.4–30.1°
b = 22.2867 (11) Å	µ = 0.12 mm−1
c = 7.1112 (4) Å	T = 100 K
β = 114.587 (4)°	Plate, colourless
V = 943.13 (8) Å3	0.38 × 0.14 × 0.08 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	2176 independent reflections
Radiation source: fine-focus sealed tube	1483 reflections with I > 2σ(I)
graphite	Rint = 0.066
φ and ω scans	θmax = 27.5°, θmin = 3.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −8→8
Tmin = 0.956, Tmax = 0.991	k = −28→28
7174 measured reflections	l = −9→8

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.150	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0786P)2] where P = (Fo2 + 2Fc2)/3
2176 reflections	(Δ/σ)max = 0.001
148 parameters	Δρmax = 0.44 e Å−3
0 restraints	Δρmin = −0.46 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
O1	−0.1281 (3)	0.19522 (7)	0.2994 (3)	0.0174 (4)
O2	−0.4204 (3)	0.24560 (7)	0.2995 (3)	0.0153 (4)
O3	0.4285 (3)	0.34855 (7)	0.2828 (3)	0.0176 (4)
O4	0.1374 (3)	0.40250 (7)	0.2633 (3)	0.0189 (4)
N1	−0.2764 (4)	0.44695 (9)	0.2808 (3)	0.0171 (5)
N2	−0.4551 (3)	0.62442 (9)	0.2152 (3)	0.0151 (5)
C1	−0.5396 (4)	0.52400 (10)	0.2605 (4)	0.0151 (5)
H1A	−0.6369	0.4962	0.2769	0.018*
C2	−0.5929 (4)	0.58295 (10)	0.2401 (4)	0.0155 (5)
H2A	−0.7272	0.5953	0.2432	0.019*
C3	−0.2614 (4)	0.60783 (10)	0.2064 (4)	0.0156 (5)
H3A	−0.1701	0.6368	0.1864	0.019*
C4	−0.1974 (4)	0.54940 (10)	0.2261 (4)	0.0159 (5)
H4A	−0.0632	0.5387	0.2195	0.019*
C5	−0.3347 (4)	0.50458 (10)	0.2570 (4)	0.0132 (5)
C6	−0.2223 (4)	0.24291 (10)	0.3003 (4)	0.0124 (5)
C7	−0.1087 (4)	0.30270 (9)	0.3032 (4)	0.0119 (5)
H7A	−0.2001	0.3251	0.1798	0.014*
H7B	−0.1002	0.3257	0.4220	0.014*
C8	0.1262 (4)	0.29562 (10)	0.3127 (4)	0.0124 (5)
H8A	0.2230	0.2786	0.4458	0.015*
H8B	0.1206	0.2674	0.2067	0.015*
C9	0.2288 (4)	0.35388 (10)	0.2832 (4)	0.0136 (5)
H1O3	0.4901	0.3032	0.2838	0.016*
H1N1	−0.378 (4)	0.4190 (13)	0.292 (4)	0.020 (7)*
H1N2	−0.490 (5)	0.6636 (14)	0.204 (4)	0.027 (8)*
H2N1	−0.155 (5)	0.4361 (11)	0.273 (4)	0.013 (6)*

	U11	U22	U33	U12	U13	U23
O1	0.0163 (9)	0.0058 (8)	0.0317 (11)	−0.0004 (6)	0.0114 (8)	−0.0008 (7)
O2	0.0120 (8)	0.0061 (8)	0.0294 (11)	−0.0011 (6)	0.0102 (8)	0.0000 (6)
O3	0.0139 (9)	0.0067 (8)	0.0366 (12)	0.0003 (6)	0.0149 (8)	0.0014 (7)
O4	0.0182 (9)	0.0057 (8)	0.0358 (12)	0.0021 (6)	0.0141 (8)	0.0021 (7)
N1	0.0141 (10)	0.0079 (10)	0.0326 (14)	0.0014 (8)	0.0131 (10)	0.0008 (8)
N2	0.0170 (11)	0.0035 (10)	0.0235 (13)	0.0024 (7)	0.0071 (9)	0.0001 (8)
C1	0.0144 (12)	0.0104 (12)	0.0225 (15)	−0.0008 (8)	0.0096 (11)	0.0020 (9)
C2	0.0142 (12)	0.0092 (12)	0.0240 (15)	0.0000 (8)	0.0089 (11)	0.0002 (9)
C3	0.0139 (12)	0.0131 (12)	0.0204 (14)	−0.0026 (9)	0.0076 (11)	0.0010 (10)
C4	0.0125 (12)	0.0111 (12)	0.0255 (15)	−0.0021 (8)	0.0093 (11)	−0.0014 (9)
C5	0.0147 (11)	0.0092 (11)	0.0137 (13)	−0.0011 (8)	0.0038 (10)	−0.0012 (9)
C6	0.0128 (11)	0.0082 (11)	0.0162 (14)	−0.0009 (8)	0.0060 (10)	0.0000 (9)
C7	0.0117 (11)	0.0067 (11)	0.0175 (14)	0.0002 (8)	0.0063 (10)	0.0005 (9)
C8	0.0115 (11)	0.0063 (11)	0.0205 (14)	−0.0005 (8)	0.0076 (10)	0.0004 (9)
C9	0.0122 (11)	0.0107 (12)	0.0195 (14)	−0.0002 (8)	0.0081 (11)	−0.0001 (9)

O1—C6	1.230 (3)	C1—H1A	0.9300
O2—C6	1.295 (3)	C2—H2A	0.9300
O3—C9	1.313 (3)	C3—C4	1.357 (3)
O3—H1O3	1.0871	C3—H3A	0.9300
O4—C9	1.217 (3)	C4—C5	1.420 (3)
N1—C5	1.331 (3)	C4—H4A	0.9300
N1—H1N1	0.94 (3)	C6—C7	1.522 (3)
N1—H2N1	0.86 (3)	C7—C8	1.519 (3)
N2—C3	1.347 (3)	C7—H7A	0.9700
N2—C2	1.354 (3)	C7—H7B	0.9700
N2—H1N2	0.90 (3)	C8—C9	1.516 (3)
C1—C2	1.352 (3)	C8—H8A	0.9700
C1—C5	1.419 (3)	C8—H8B	0.9700
C9—O3—H1O3	116.8	N1—C5—C4	122.1 (2)
C5—N1—H1N1	118.3 (16)	C1—C5—C4	116.8 (2)
C5—N1—H2N1	119.4 (17)	O1—C6—O2	122.88 (19)
H1N1—N1—H2N1	122 (2)	O1—C6—C7	120.88 (19)
C3—N2—C2	120.7 (2)	O2—C6—C7	116.24 (18)
C3—N2—H1N2	118.4 (17)	C8—C7—C6	112.93 (18)
C2—N2—H1N2	120.9 (17)	C8—C7—H7A	109.0
C2—C1—C5	119.9 (2)	C6—C7—H7A	109.0
C2—C1—H1A	120.1	C8—C7—H7B	109.0
C5—C1—H1A	120.1	C6—C7—H7B	109.0
C1—C2—N2	121.4 (2)	H7A—C7—H7B	107.8
C1—C2—H2A	119.3	C9—C8—C7	113.79 (18)
N2—C2—H2A	119.3	C9—C8—H8A	108.8
N2—C3—C4	121.0 (2)	C7—C8—H8A	108.8
N2—C3—H3A	119.5	C9—C8—H8B	108.8
C4—C3—H3A	119.5	C7—C8—H8B	108.8
C3—C4—C5	120.2 (2)	H8A—C8—H8B	107.7
C3—C4—H4A	119.9	O4—C9—O3	121.5 (2)
C5—C4—H4A	119.9	O4—C9—C8	123.62 (19)
N1—C5—C1	121.0 (2)	O3—C9—C8	114.91 (18)
C5—C1—C2—N2	0.3 (4)	C3—C4—C5—C1	1.5 (4)
C3—N2—C2—C1	1.2 (4)	O1—C6—C7—C8	−2.1 (3)
C2—N2—C3—C4	−1.3 (4)	O2—C6—C7—C8	177.7 (2)
N2—C3—C4—C5	−0.1 (4)	C6—C7—C8—C9	171.3 (2)
C2—C1—C5—N1	178.7 (2)	C7—C8—C9—O4	3.3 (3)
C2—C1—C5—C4	−1.6 (4)	C7—C8—C9—O3	−177.5 (2)
C3—C4—C5—N1	−178.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1O3···O2i	1.09	1.40	2.482 (2)	176
N1—H1N1···O3ii	0.94 (3)	2.00 (3)	2.926 (3)	168 (3)
N2—H1N2···O1iii	0.90 (3)	2.59 (3)	3.115 (3)	118 (3)
N2—H1N2···O2iii	0.90 (3)	1.92 (3)	2.810 (3)	174 (3)
N1—H2N1···O4	0.85 (3)	2.08 (3)	2.934 (3)	175 (2)
C1—H1A···O4ii	0.93	2.54	3.440 (3)	164
C2—H2A···O1iii	0.93	2.39	3.041 (3)	127
C3—H3A···O1iv	0.93	2.31	3.222 (3)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H1O3⋯O2i	1.09	1.40	2.482 (2)	176
N1—H1N1⋯O3ii	0.94 (3)	2.00 (3)	2.926 (3)	168 (3)
N2—H1N2⋯O1iii	0.90 (3)	2.59 (3)	3.115 (3)	118 (3)
N2—H1N2⋯O2iii	0.90 (3)	1.92 (3)	2.810 (3)	174 (3)
N1—H2N1⋯O4	0.85 (3)	2.08 (3)	2.934 (3)	175 (2)
C1—H1A⋯O4ii	0.93	2.54	3.440 (3)	164
C2—H2A⋯O1iii	0.93	2.39	3.041 (3)	127
C3—H3A⋯O1iv	0.93	2.31	3.222 (3)	166

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .