2,3-Diamino-pyridinium 2-hy-droxy-benzoate.

In the title mol-ecular salt, C(5)H(8)N(3) (+)·C(7)H(5)O(3) (-), the 2,3-diamino-pyridinium cation is essentially planar, with a maximum deviation of 0.006 (2) Å. In the crystal, adjacent cations and anions are linked by pairs of N-H⋯O hydrogen bonds, generating R(2) (2)(8) loops. These dimers are linked by further N-H⋯O hydrogen bonds and C-H⋯O inter-actions to form sheets lying parallel to (001). A typical intra-molecular O-H⋯O hydrogen bond is also observed in the salicylate (2-hy-droxy-benzoate) anion, which generates an S(6) ring. The crystal structure also features π-π stacking inter-actions between the pyridinium rings of the cations, with a centroid-centroid distance of 3.5896 (15) Å.

Related literature

For details of 2-amino­pyridine and its derivatives, see: Banerjee & Murugavel (2004 ▶); Bis & Zaworotko (2005 ▶); Bis et al. (2006 ▶). For n class="Chemical">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

C5H8N3 +·n class="Chemical">C7H5O3 −

M = 247.25

Orthorhombic,

a = 10.484 (3) Å

b = 11.260 (3) Å

c = 20.033 (6) Å

V = 2364.9 (12) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.54 × 0.47 × 0.10 mm

Data collection

Bruker APEXII DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.947, T max = 0.990

12688 measured reflections

3388 independent reflections

1989 reflections with I > 2σ(I)

R int = 0.063

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.144

S = 1.03

3388 reflections

216 parameters

All H-atom parameters refined

Δρmax = 0.21 e Å−3

Δρmin = −0.21 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 datablock(s) global, I. DOI: 10.1107/S1600536811044461/hb6455sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811044461/hb6455Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811044461/hb6455Isup3.cml

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

C5H8N3+·C7H5O3−	F(000) = 1040
Mr = 247.25	Dx = 1.389 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2044 reflections
a = 10.484 (3) Å	θ = 2.8–27.3°
b = 11.260 (3) Å	µ = 0.10 mm−1
c = 20.033 (6) Å	T = 100 K
V = 2364.9 (12) Å3	Plate, brown
Z = 8	0.54 × 0.47 × 0.10 mm

Bruker APEXII DUO CCD diffractometer	3388 independent reflections
Radiation source: fine-focus sealed tube	1989 reflections with I > 2σ(I)
graphite	Rint = 0.063
φ and ω scans	θmax = 30.0°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −14→14
Tmin = 0.947, Tmax = 0.990	k = −8→15
12688 measured reflections	l = −27→23

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)] = 0.050	All H-atom parameters refined
wR(F2) = 0.144	w = 1/[σ2(Fo2) + (0.0573P)2 + 0.2876P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3388 reflections	Δρmax = 0.21 e Å−3
216 parameters	Δρmin = −0.21 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0084 (15)

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 esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.28118 (14)	0.47769 (11)	0.49919 (8)	0.0372 (3)
N2	0.31269 (15)	0.31738 (13)	0.42951 (8)	0.0399 (4)
N3	0.49319 (18)	0.22674 (14)	0.52153 (10)	0.0515 (4)
C1	0.34064 (15)	0.37422 (13)	0.48633 (8)	0.0329 (4)
C2	0.43007 (15)	0.33158 (13)	0.53385 (9)	0.0356 (4)
C3	0.45227 (17)	0.39879 (16)	0.58971 (10)	0.0427 (4)
C4	0.38911 (19)	0.50631 (16)	0.60051 (11)	0.0462 (5)
C5	0.30414 (18)	0.54408 (15)	0.55483 (10)	0.0441 (4)
O1	−0.04088 (13)	0.39481 (11)	0.24975 (8)	0.0517 (4)
O2	0.09892 (12)	0.57050 (10)	0.41657 (6)	0.0432 (3)
O3	0.08969 (11)	0.40353 (9)	0.35839 (6)	0.0392 (3)
C6	−0.09061 (16)	0.50000 (14)	0.26928 (9)	0.0377 (4)
C7	−0.18426 (18)	0.54995 (18)	0.22901 (11)	0.0494 (5)
C8	−0.23979 (19)	0.65666 (18)	0.24675 (11)	0.0502 (5)
C9	−0.20179 (18)	0.71566 (17)	0.30334 (11)	0.0475 (5)
C10	−0.10732 (17)	0.66749 (14)	0.34298 (10)	0.0418 (4)
C11	−0.04980 (14)	0.55892 (13)	0.32692 (9)	0.0331 (4)
C12	0.05192 (15)	0.50816 (13)	0.37001 (8)	0.0331 (4)
H3	0.5167 (19)	0.3712 (17)	0.6237 (10)	0.056 (6)*
H4	0.4035 (18)	0.5488 (16)	0.6398 (10)	0.049 (5)*
H5	0.2538 (19)	0.6171 (18)	0.5580 (10)	0.054 (5)*
H7	−0.212 (2)	0.5068 (18)	0.1886 (12)	0.066 (6)*
H8	−0.304 (2)	0.6964 (16)	0.2196 (10)	0.050 (5)*
H9	−0.2398 (17)	0.7915 (16)	0.3162 (9)	0.042 (5)*
H10	−0.0825 (19)	0.7010 (16)	0.3859 (11)	0.048 (5)*
H1O1	0.016 (2)	0.3733 (17)	0.2853 (11)	0.059 (6)*
H1N1	0.224 (2)	0.5073 (16)	0.4672 (10)	0.048 (5)*
H1N2	0.2509 (18)	0.3436 (15)	0.4020 (10)	0.038 (5)*
H2N2	0.3459 (18)	0.2443 (19)	0.4211 (10)	0.054 (6)*
H1N3	0.465 (2)	0.1816 (17)	0.4864 (11)	0.056 (6)*
H2N3	0.536 (2)	0.1958 (16)	0.5553 (11)	0.052 (6)*

	U11	U22	U33	U12	U13	U23
N1	0.0357 (8)	0.0335 (7)	0.0423 (9)	0.0034 (6)	−0.0022 (7)	−0.0001 (6)
N2	0.0419 (8)	0.0376 (7)	0.0401 (9)	0.0062 (7)	−0.0096 (7)	−0.0050 (6)
N3	0.0599 (11)	0.0414 (8)	0.0531 (11)	0.0154 (8)	−0.0212 (9)	−0.0047 (8)
C1	0.0295 (8)	0.0312 (7)	0.0380 (9)	−0.0034 (6)	−0.0004 (7)	0.0020 (6)
C2	0.0347 (8)	0.0330 (7)	0.0391 (10)	−0.0017 (7)	−0.0035 (7)	0.0037 (7)
C3	0.0405 (10)	0.0447 (9)	0.0429 (11)	−0.0018 (8)	−0.0079 (8)	0.0017 (8)
C4	0.0495 (11)	0.0454 (9)	0.0436 (11)	−0.0020 (9)	−0.0021 (9)	−0.0086 (8)
C5	0.0453 (10)	0.0373 (8)	0.0496 (12)	0.0035 (8)	−0.0010 (9)	−0.0071 (8)
O1	0.0476 (8)	0.0510 (8)	0.0565 (9)	0.0040 (6)	−0.0077 (7)	−0.0173 (6)
O2	0.0458 (7)	0.0389 (6)	0.0449 (8)	0.0057 (5)	−0.0135 (6)	−0.0061 (5)
O3	0.0405 (6)	0.0319 (6)	0.0453 (7)	0.0023 (5)	0.0005 (5)	−0.0002 (5)
C6	0.0315 (8)	0.0394 (8)	0.0423 (10)	−0.0046 (7)	0.0007 (7)	−0.0031 (7)
C7	0.0397 (10)	0.0614 (12)	0.0471 (12)	−0.0056 (9)	−0.0103 (9)	−0.0050 (9)
C8	0.0377 (10)	0.0561 (11)	0.0568 (13)	0.0006 (9)	−0.0133 (9)	0.0056 (9)
C9	0.0405 (10)	0.0403 (9)	0.0617 (13)	0.0022 (8)	−0.0126 (9)	0.0024 (9)
C10	0.0380 (9)	0.0362 (8)	0.0513 (12)	0.0001 (7)	−0.0092 (8)	−0.0021 (8)
C11	0.0276 (8)	0.0321 (7)	0.0395 (10)	−0.0052 (6)	−0.0004 (7)	0.0019 (6)
C12	0.0304 (8)	0.0324 (7)	0.0366 (9)	−0.0028 (6)	0.0031 (7)	0.0032 (7)

N1—C1	1.346 (2)	O1—C6	1.352 (2)
N1—C5	1.364 (2)	O1—H1O1	0.96 (2)
N1—H1N1	0.94 (2)	O2—C12	1.267 (2)
N2—C1	1.338 (2)	O3—C12	1.2646 (19)
N2—H1N2	0.90 (2)	C6—C7	1.390 (3)
N2—H2N2	0.91 (2)	C6—C11	1.399 (2)
N3—C2	1.376 (2)	C7—C8	1.382 (3)
N3—H1N3	0.92 (2)	C7—H7	0.99 (2)
N3—H2N3	0.88 (2)	C8—C9	1.373 (3)
C1—C2	1.420 (2)	C8—H8	0.97 (2)
C2—C3	1.371 (3)	C9—C10	1.380 (3)
C3—C4	1.397 (3)	C9—H9	0.977 (18)
C3—H3	1.01 (2)	C10—C11	1.401 (2)
C4—C5	1.346 (3)	C10—H10	0.97 (2)
C4—H4	0.93 (2)	C11—C12	1.486 (2)
C5—H5	0.98 (2)
C1—N1—C5	123.31 (15)	N1—C5—H5	114.7 (12)
C1—N1—H1N1	118.2 (12)	C6—O1—H1O1	104.2 (12)
C5—N1—H1N1	118.4 (12)	O1—C6—C7	117.32 (16)
C1—N2—H1N2	121.4 (12)	O1—C6—C11	122.45 (16)
C1—N2—H2N2	120.4 (13)	C7—C6—C11	120.22 (16)
H1N2—N2—H2N2	117.3 (17)	C8—C7—C6	120.02 (18)
C2—N3—H1N3	117.2 (13)	C8—C7—H7	120.9 (12)
C2—N3—H2N3	116.5 (13)	C6—C7—H7	119.1 (12)
H1N3—N3—H2N3	122.2 (18)	C9—C8—C7	120.72 (19)
N2—C1—N1	118.37 (15)	C9—C8—H8	116.0 (11)
N2—C1—C2	123.58 (15)	C7—C8—H8	123.2 (11)
N1—C1—C2	118.05 (15)	C8—C9—C10	119.54 (18)
C3—C2—N3	122.58 (16)	C8—C9—H9	121.5 (11)
C3—C2—C1	118.21 (15)	C10—C9—H9	118.9 (11)
N3—C2—C1	119.18 (16)	C9—C10—C11	121.31 (17)
C2—C3—C4	121.63 (17)	C9—C10—H10	123.2 (11)
C2—C3—H3	119.6 (11)	C11—C10—H10	115.2 (11)
C4—C3—H3	118.7 (11)	C6—C11—C10	118.16 (15)
C5—C4—C3	118.84 (18)	C6—C11—C12	121.10 (14)
C5—C4—H4	121.2 (12)	C10—C11—C12	120.74 (15)
C3—C4—H4	119.9 (12)	O3—C12—O2	122.00 (15)
C4—C5—N1	119.95 (17)	O3—C12—C11	118.43 (14)
C4—C5—H5	125.3 (12)	O2—C12—C11	119.57 (14)
C5—N1—C1—N2	−178.69 (16)	C6—C7—C8—C9	1.3 (3)
C5—N1—C1—C2	1.1 (2)	C7—C8—C9—C10	−0.2 (3)
N2—C1—C2—C3	178.90 (16)	C8—C9—C10—C11	−0.5 (3)
N1—C1—C2—C3	−0.9 (2)	O1—C6—C11—C10	−179.94 (16)
N2—C1—C2—N3	0.5 (3)	C7—C6—C11—C10	1.0 (2)
N1—C1—C2—N3	−179.27 (15)	O1—C6—C11—C12	0.2 (2)
N3—C2—C3—C4	178.57 (18)	C7—C6—C11—C12	−178.86 (16)
C1—C2—C3—C4	0.2 (3)	C9—C10—C11—C6	0.0 (3)
C2—C3—C4—C5	0.2 (3)	C9—C10—C11—C12	179.93 (16)
C3—C4—C5—N1	−0.1 (3)	C6—C11—C12—O3	−8.9 (2)
C1—N1—C5—C4	−0.6 (3)	C10—C11—C12—O3	171.22 (15)
O1—C6—C7—C8	179.24 (17)	C6—C11—C12—O2	170.49 (15)
C11—C6—C7—C8	−1.7 (3)	C10—C11—C12—O2	−9.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O3	0.96 (2)	1.69 (2)	2.573 (2)	151.2 (18)
N1—H1N1···O2	0.94 (2)	1.80 (2)	2.736 (2)	171.1 (19)
N2—H1N2···O3	0.900 (19)	2.019 (19)	2.905 (2)	167.7 (18)
N2—H2N2···O2i	0.91 (2)	2.04 (2)	2.942 (2)	169.6 (18)
N3—H1N3···O2i	0.92 (2)	1.99 (2)	2.907 (2)	174.3 (19)
N3—H2N3···O3ii	0.88 (2)	2.14 (2)	2.994 (2)	163.9 (19)
C7—H7···O3iii	0.99 (2)	2.56 (2)	3.376 (3)	139.8 (17)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯O3	0.96 (2)	1.69 (2)	2.573 (2)	151.2 (18)
N1—H1N1⋯O2	0.94 (2)	1.80 (2)	2.736 (2)	171.1 (19)
N2—H1N2⋯O3	0.900 (19)	2.019 (19)	2.905 (2)	167.7 (18)
N2—H2N2⋯O2i	0.91 (2)	2.04 (2)	2.942 (2)	169.6 (18)
N3—H1N3⋯O2i	0.92 (2)	1.99 (2)	2.907 (2)	174.3 (19)
N3—H2N3⋯O3ii	0.88 (2)	2.14 (2)	2.994 (2)	163.9 (19)
C7—H7⋯O3iii	0.99 (2)	2.56 (2)	3.376 (3)	139.8 (17)

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