4-Amino-pyridinium 2-hy-droxy-benzoate.

In the salicylate anion of the title salt, C(5)H(7)N(2) (+)·C(7)H(5)O(3) (-), an intra-molecular O-H⋯O hydrogen bond generating an S(6) ring motif is observed. In the crystal structure, the cations and anions are linked into a two-dimensional network parallel to the ab plane by N-H⋯O and C-H⋯O hydrogen bonds. The network contains R(2) (2)(7) and R(1) (2)(4) ring motifs. Weak π-π inter-actions between the benzene and pyridinium rings [centroid-centroid distance = 3.688 (1) Å] are also observed.

Related literature

For the biological activity of 4-amino­pyridine, see: Schwid et al. (1997 ▶). For the crystal structure of 4-amino­pyridine, see: Chao & Schempp (1977 ▶); Anderson et al. (2005 ▶). For related structures, see: Bhattacharya et al. (1994 ▶); Karle et al. (2003 ▶); Gellert & Hsu (1988 ▶); Hemamalini & Fun (2010 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C5H7N2 +·C7H5O3 −

M = 232.24

Orthorhombic,

a = 12.5801 (2) Å

b = 11.4157 (2) Å

c = 15.7560 (3) Å

V = 2262.73 (7) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.29 × 0.17 × 0.08 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.971, T max = 0.992

15672 measured reflections

3010 independent reflections

2303 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.118

S = 1.09

3010 reflections

170 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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/S1600536810027042/ci5130sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810027042/ci5130Isup2.hkl

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

C5H7N2+·C7H5O3−	F(000) = 976
Mr = 232.24	Dx = 1.363 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2403 reflections
a = 12.5801 (2) Å	θ = 2.6–28.5°
b = 11.4157 (2) Å	µ = 0.10 mm−1
c = 15.7560 (3) Å	T = 100 K
V = 2262.73 (7) Å3	Plate, colourless
Z = 8	0.29 × 0.17 × 0.08 mm

Bruker SMART APEXII CCD area-detector diffractometer	3010 independent reflections
Radiation source: fine-focus sealed tube	2303 reflections with I > 2σ(I)
graphite	Rint = 0.057
φ and ω scans	θmax = 29.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −17→11
Tmin = 0.971, Tmax = 0.992	k = −15→15
15672 measured reflections	l = −21→16

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.0323P)2 + 1.7134P] where P = (Fo2 + 2Fc2)/3
3010 reflections	(Δ/σ)max = 0.001
170 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

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

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.93694 (11)	0.70642 (11)	0.39307 (9)	0.0267 (3)
O2	1.08510 (10)	0.38258 (10)	0.38336 (8)	0.0216 (3)
O3	1.08570 (10)	0.56634 (10)	0.43059 (8)	0.0204 (3)
C1	0.89745 (14)	0.62078 (15)	0.34345 (11)	0.0184 (4)
C2	0.80559 (14)	0.64452 (17)	0.29653 (12)	0.0227 (4)
H2A	0.7739	0.7180	0.2999	0.027*
C3	0.76181 (15)	0.55938 (18)	0.24519 (12)	0.0255 (4)
H3A	0.7003	0.5757	0.2146	0.031*
C4	0.80871 (15)	0.44924 (17)	0.23863 (12)	0.0242 (4)
H4A	0.7792	0.3923	0.2036	0.029*
C5	0.89968 (14)	0.42548 (16)	0.28476 (11)	0.0203 (4)
H5A	0.9312	0.3520	0.2802	0.024*
C6	0.94544 (13)	0.50956 (15)	0.33810 (11)	0.0163 (3)
C7	1.04482 (14)	0.48238 (15)	0.38720 (11)	0.0164 (3)
N1	0.76523 (12)	0.02312 (13)	0.49686 (9)	0.0182 (3)
N2	1.02794 (13)	0.14710 (14)	0.37198 (11)	0.0217 (3)
C8	0.82546 (14)	−0.05055 (15)	0.45039 (11)	0.0186 (4)
H8A	0.8061	−0.1290	0.4468	0.022*
C9	0.91367 (14)	−0.01310 (15)	0.40865 (11)	0.0178 (4)
H9A	0.9543	−0.0655	0.3772	0.021*
C10	0.94313 (13)	0.10635 (14)	0.41341 (11)	0.0162 (3)
C11	0.87938 (14)	0.18104 (15)	0.46358 (11)	0.0170 (4)
H11A	0.8970	0.2598	0.4692	0.020*
C12	0.79224 (14)	0.13756 (15)	0.50369 (11)	0.0186 (4)
H12A	0.7504	0.1873	0.5364	0.022*
H1N1	0.7029 (19)	−0.003 (2)	0.5260 (15)	0.039 (7)*
H2N2	1.0665 (18)	0.102 (2)	0.3412 (15)	0.032 (6)*
H1N2	1.0479 (19)	0.222 (2)	0.3735 (15)	0.042 (7)*
H1O1	1.000 (2)	0.669 (2)	0.4166 (18)	0.061 (9)*

	U11	U22	U33	U12	U13	U23
O1	0.0301 (8)	0.0199 (7)	0.0302 (8)	0.0066 (6)	−0.0086 (6)	−0.0064 (5)
O2	0.0199 (6)	0.0150 (6)	0.0297 (7)	0.0019 (5)	−0.0014 (6)	−0.0015 (5)
O3	0.0196 (6)	0.0173 (6)	0.0242 (7)	−0.0002 (5)	−0.0051 (5)	−0.0032 (5)
C1	0.0177 (8)	0.0214 (9)	0.0162 (9)	−0.0010 (7)	0.0016 (7)	−0.0002 (7)
C2	0.0191 (9)	0.0280 (9)	0.0210 (10)	0.0050 (8)	0.0032 (7)	0.0042 (7)
C3	0.0151 (9)	0.0420 (11)	0.0195 (9)	−0.0039 (8)	−0.0022 (7)	0.0081 (8)
C4	0.0243 (10)	0.0305 (10)	0.0179 (9)	−0.0106 (8)	−0.0027 (8)	0.0005 (8)
C5	0.0224 (9)	0.0200 (8)	0.0184 (9)	−0.0060 (7)	0.0012 (7)	0.0008 (7)
C6	0.0151 (8)	0.0193 (8)	0.0146 (8)	−0.0035 (7)	0.0016 (6)	0.0002 (6)
C7	0.0154 (8)	0.0176 (8)	0.0162 (8)	−0.0026 (7)	0.0014 (7)	0.0006 (6)
N1	0.0153 (7)	0.0189 (7)	0.0205 (8)	−0.0016 (6)	0.0007 (6)	0.0020 (6)
N2	0.0219 (8)	0.0166 (8)	0.0265 (9)	−0.0017 (7)	0.0073 (7)	−0.0021 (6)
C8	0.0201 (9)	0.0148 (8)	0.0209 (9)	−0.0010 (7)	−0.0027 (7)	0.0003 (7)
C9	0.0195 (8)	0.0149 (8)	0.0190 (9)	0.0021 (7)	0.0005 (7)	−0.0014 (6)
C10	0.0158 (8)	0.0174 (8)	0.0155 (8)	0.0003 (6)	−0.0020 (7)	0.0014 (6)
C11	0.0191 (9)	0.0147 (8)	0.0171 (9)	0.0006 (7)	−0.0025 (7)	−0.0009 (6)
C12	0.0200 (9)	0.0183 (8)	0.0175 (9)	0.0036 (7)	−0.0009 (7)	−0.0016 (7)

O1—C1	1.347 (2)	N1—C8	1.348 (2)
O1—H1O1	0.97 (3)	N1—C12	1.354 (2)
O2—C7	1.248 (2)	N1—H1N1	0.96 (2)
O3—C7	1.285 (2)	N2—C10	1.335 (2)
C1—C2	1.398 (3)	N2—H2N2	0.86 (2)
C1—C6	1.408 (2)	N2—H1N2	0.89 (3)
C2—C3	1.379 (3)	C8—C9	1.359 (2)
C2—H2A	0.93	C8—H8A	0.93
C3—C4	1.393 (3)	C9—C10	1.415 (2)
C3—H3A	0.93	C9—H9A	0.93
C4—C5	1.382 (3)	C10—C11	1.412 (2)
C4—H4A	0.93	C11—C12	1.359 (2)
C5—C6	1.400 (2)	C11—H11A	0.93
C5—H5A	0.93	C12—H12A	0.93
C6—C7	1.503 (2)
C1—O1—H1O1	101.7 (16)	C8—N1—C12	120.26 (16)
O1—C1—C2	118.11 (16)	C8—N1—H1N1	122.0 (14)
O1—C1—C6	122.07 (16)	C12—N1—H1N1	117.7 (14)
C2—C1—C6	119.82 (16)	C10—N2—H2N2	121.1 (15)
C3—C2—C1	120.23 (17)	C10—N2—H1N2	123.1 (16)
C3—C2—H2A	119.9	H2N2—N2—H1N2	116 (2)
C1—C2—H2A	119.9	N1—C8—C9	121.71 (16)
C2—C3—C4	120.70 (18)	N1—C8—H8A	119.1
C2—C3—H3A	119.7	C9—C8—H8A	119.1
C4—C3—H3A	119.7	C8—C9—C10	119.43 (16)
C5—C4—C3	119.26 (17)	C8—C9—H9A	120.3
C5—C4—H4A	120.4	C10—C9—H9A	120.3
C3—C4—H4A	120.4	N2—C10—C11	121.15 (16)
C4—C5—C6	121.44 (17)	N2—C10—C9	121.29 (16)
C4—C5—H5A	119.3	C11—C10—C9	117.56 (16)
C6—C5—H5A	119.3	C12—C11—C10	119.85 (16)
C5—C6—C1	118.54 (16)	C12—C11—H11A	120.1
C5—C6—C7	120.65 (16)	C10—C11—H11A	120.1
C1—C6—C7	120.80 (15)	N1—C12—C11	121.17 (16)
O2—C7—O3	122.97 (16)	N1—C12—H12A	119.4
O2—C7—C6	120.08 (15)	C11—C12—H12A	119.4
O3—C7—C6	116.94 (15)
O1—C1—C2—C3	−179.61 (17)	C1—C6—C7—O2	178.36 (16)
C6—C1—C2—C3	0.1 (3)	C5—C6—C7—O3	175.74 (16)
C1—C2—C3—C4	−0.6 (3)	C1—C6—C7—O3	−3.0 (2)
C2—C3—C4—C5	0.5 (3)	C12—N1—C8—C9	−0.6 (3)
C3—C4—C5—C6	0.2 (3)	N1—C8—C9—C10	−0.4 (3)
C4—C5—C6—C1	−0.7 (3)	C8—C9—C10—N2	−178.64 (17)
C4—C5—C6—C7	−179.52 (16)	C8—C9—C10—C11	1.3 (2)
O1—C1—C6—C5	−179.75 (16)	N2—C10—C11—C12	178.68 (17)
C2—C1—C6—C5	0.6 (2)	C9—C10—C11—C12	−1.2 (2)
O1—C1—C6—C7	−0.9 (3)	C8—N1—C12—C11	0.6 (3)
C2—C1—C6—C7	179.35 (16)	C10—C11—C12—N1	0.3 (3)
C5—C6—C7—O2	−2.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O2i	0.96 (2)	2.48 (2)	3.1394 (19)	126 (2)
N1—H1N1···O3i	0.96 (2)	1.78 (2)	2.7296 (19)	172 (2)
N2—H1N2···O2	0.89 (2)	1.90 (2)	2.789 (2)	176 (2)
O1—H1O1···O3	0.97 (3)	1.61 (2)	2.5316 (18)	157 (2)
C11—H11A···O3ii	0.93	2.55	3.360 (2)	146
C12—H12A···O2i	0.93	2.56	3.164 (2)	123

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O2i	0.96 (2)	2.48 (2)	3.1394 (19)	126 (2)
N1—H1N1⋯O3i	0.96 (2)	1.78 (2)	2.7296 (19)	172 (2)
N2—H1N2⋯O2	0.89 (2)	1.90 (2)	2.789 (2)	176 (2)
O1—H1O1⋯O3	0.97 (3)	1.61 (2)	2.5316 (18)	157 (2)
C11—H11A⋯O3ii	0.93	2.55	3.360 (2)	146
C12—H12A⋯O2i	0.93	2.56	3.164 (2)	123

Symmetry codes: (i) ; (ii) .