2-Amino-5-bromo-pyridinium 2-hy-droxy-benzoate.

In the title compound, C(5)H(6)BrN(2) (+)·C(7)H(5)O(3) (-), the 2-amino-5-bromo-pyridinium cation and 2-hy-droxy-benzoate anion are essentially planar with maximum deviations of 0.020 (1) and 0.018 (2) Å, respectively. The anion is stabilized by an intra-molecular O-H⋯O hydrogen bond, which generates an S(6) ring motif. In the crystal, the cations and anions are linked by N-H⋯O hydrogen bonds into chains propagating along [010]. The chains contain R(2) (2)(8) ring motifs. The structure is further stabilized by π-π stacking inter-actions [centroid-centroid distances = 3.4908 (10) and 3.5927 (10) Å] and also features short Br⋯O contacts [2.9671 (13) Å].

Related literature

For details of non-covalent inter­actions, see: Remenar et al. (2003 ▶); Sokolov et al. (2006 ▶). For the importance of salicylic acid, see: Sticher et al. (1997 ▶); Rairdan & Delaney (2002 ▶); Nawrath & Métraux (1999 ▶); Wildermuth et al. (2001 ▶). For related structures, see: Quah et al. (2008 ▶, 2010a ▶,b ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶). For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C5H6BrN2 +·C7H5O3 −

M = 311.14

Monoclinic,

a = 8.9498 (2) Å

b = 10.8673 (2) Å

c = 13.1277 (3) Å

β = 108.704 (1)°

V = 1209.37 (4) Å3

Z = 4

Mo Kα radiation

μ = 3.40 mm−1

T = 100 K

0.48 × 0.27 × 0.19 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.291, T max = 0.572

13299 measured reflections

3559 independent reflections

2942 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.070

S = 1.12

3559 reflections

179 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.62 e Å−3

Δρmin = −0.48 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/S1600536810029855/ci5140sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810029855/ci5140Isup2.hkl

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

C5H6BrN2+·C7H5O3−	F(000) = 624
Mr = 311.14	Dx = 1.709 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6239 reflections
a = 8.9498 (2) Å	θ = 2.4–30.1°
b = 10.8673 (2) Å	µ = 3.40 mm−1
c = 13.1277 (3) Å	T = 100 K
β = 108.704 (1)°	Block, yellow
V = 1209.37 (4) Å3	0.48 × 0.27 × 0.19 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	3559 independent reflections
Radiation source: fine-focus sealed tube	2942 reflections with I > 2σ(I)
graphite	Rint = 0.023
φ and ω scans	θmax = 30.1°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→12
Tmin = 0.291, Tmax = 0.572	k = −12→15
13299 measured reflections	l = −17→18

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.070	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ2(Fo2) + (0.0315P)2 + 0.5751P] where P = (Fo2 + 2Fc2)/3
3559 reflections	(Δ/σ)max = 0.001
179 parameters	Δρmax = 0.62 e Å−3
0 restraints	Δρmin = −0.48 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
O3	0.88434 (14)	0.35437 (12)	0.92381 (10)	0.0225 (3)
O2	0.98836 (15)	0.30956 (12)	1.09830 (10)	0.0237 (3)
O1	1.18787 (16)	0.14189 (12)	1.16207 (10)	0.0235 (3)
C11	1.07156 (18)	0.19199 (15)	0.97440 (13)	0.0161 (3)
C6	1.1749 (2)	0.12215 (15)	1.05740 (13)	0.0189 (3)
C10	1.06367 (18)	0.16877 (16)	0.86826 (13)	0.0181 (3)
H10	0.9957	0.2149	0.8130	0.022*
C9	1.1556 (2)	0.07793 (17)	0.84408 (14)	0.0215 (3)
H9	1.1489	0.0625	0.7731	0.026*
C12	0.97397 (19)	0.29196 (16)	0.99973 (13)	0.0178 (3)
C8	1.2582 (2)	0.00999 (18)	0.92745 (15)	0.0257 (4)
H8	1.3207	−0.0507	0.9117	0.031*
C7	1.2685 (2)	0.03150 (17)	1.03343 (14)	0.0244 (4)
H7	1.3377	−0.0143	1.0884	0.029*
H1O1	1.121 (3)	0.204 (3)	1.158 (2)	0.049 (8)*
Br1	0.370641 (18)	0.746039 (15)	0.758163 (13)	0.01948 (6)
C5	0.71709 (18)	0.56266 (15)	1.06422 (13)	0.0164 (3)
C1	0.61778 (19)	0.58819 (16)	0.87434 (13)	0.0178 (3)
H1	0.6220	0.5662	0.8069	0.021*
N2	0.81671 (17)	0.50520 (14)	1.14774 (12)	0.0196 (3)
N1	0.71750 (16)	0.53391 (13)	0.96389 (11)	0.0169 (3)
C3	0.5063 (2)	0.70608 (16)	0.98575 (14)	0.0191 (3)
H3	0.4333	0.7637	0.9926	0.023*
C2	0.51201 (18)	0.67430 (15)	0.88258 (13)	0.0174 (3)
C4	0.60740 (19)	0.65257 (16)	1.07473 (13)	0.0192 (3)
H4	0.6050	0.6747	1.1426	0.023*
H1N	0.784 (3)	0.468 (2)	0.9560 (19)	0.038 (7)*
H1N2	0.878 (3)	0.452 (2)	1.1347 (17)	0.027 (6)*
H2N2	0.820 (2)	0.5260 (19)	1.2082 (18)	0.021 (5)*

	U11	U22	U33	U12	U13	U23
O3	0.0232 (6)	0.0249 (6)	0.0173 (6)	0.0073 (5)	0.0036 (5)	−0.0019 (5)
O2	0.0309 (6)	0.0257 (7)	0.0153 (6)	0.0064 (5)	0.0085 (5)	−0.0012 (5)
O1	0.0318 (7)	0.0240 (7)	0.0143 (6)	0.0055 (5)	0.0070 (5)	0.0035 (5)
C11	0.0163 (7)	0.0153 (8)	0.0166 (7)	−0.0016 (6)	0.0053 (6)	−0.0021 (6)
C6	0.0236 (8)	0.0165 (8)	0.0166 (8)	−0.0021 (6)	0.0063 (6)	0.0006 (6)
C10	0.0181 (7)	0.0187 (8)	0.0158 (7)	0.0003 (6)	0.0031 (6)	−0.0003 (6)
C9	0.0247 (8)	0.0235 (9)	0.0165 (8)	0.0025 (7)	0.0067 (6)	−0.0026 (7)
C12	0.0173 (7)	0.0184 (7)	0.0175 (8)	−0.0007 (6)	0.0052 (6)	−0.0021 (6)
C8	0.0322 (9)	0.0220 (9)	0.0237 (9)	0.0087 (7)	0.0100 (8)	−0.0008 (7)
C7	0.0307 (9)	0.0210 (9)	0.0196 (8)	0.0077 (7)	0.0054 (7)	0.0048 (7)
Br1	0.02043 (9)	0.01984 (10)	0.01686 (9)	0.00136 (6)	0.00414 (6)	0.00213 (6)
C5	0.0174 (7)	0.0165 (7)	0.0153 (7)	−0.0037 (6)	0.0051 (6)	−0.0022 (6)
C1	0.0194 (7)	0.0205 (8)	0.0140 (7)	−0.0023 (6)	0.0059 (6)	−0.0012 (6)
N2	0.0209 (7)	0.0213 (7)	0.0158 (7)	0.0039 (6)	0.0048 (6)	−0.0009 (6)
N1	0.0184 (6)	0.0178 (7)	0.0145 (6)	0.0003 (5)	0.0054 (5)	−0.0016 (5)
C3	0.0203 (7)	0.0183 (8)	0.0207 (8)	0.0018 (6)	0.0094 (6)	−0.0004 (7)
C2	0.0172 (7)	0.0175 (8)	0.0161 (7)	−0.0002 (6)	0.0035 (6)	0.0010 (6)
C4	0.0216 (7)	0.0193 (8)	0.0175 (8)	−0.0004 (6)	0.0073 (6)	−0.0029 (6)

O3—C12	1.259 (2)	Br1—C2	1.8844 (16)
O2—C12	1.273 (2)	C5—N2	1.327 (2)
O1—C6	1.358 (2)	C5—N1	1.355 (2)
O1—H1O1	0.89 (3)	C5—C4	1.423 (2)
C11—C10	1.395 (2)	C1—C2	1.360 (2)
C11—C6	1.404 (2)	C1—N1	1.361 (2)
C11—C12	1.497 (2)	C1—H1	0.93
C6—C7	1.393 (2)	N2—H1N2	0.86 (2)
C10—C9	1.386 (2)	N2—H2N2	0.82 (2)
C10—H10	0.93	N1—H1N	0.96 (2)
C9—C8	1.393 (2)	C3—C4	1.358 (2)
C9—H9	0.93	C3—C2	1.414 (2)
C8—C7	1.384 (3)	C3—H3	0.93
C8—H8	0.93	C4—H4	0.93
C7—H7	0.93
C6—O1—H1O1	102.4 (18)	N2—C5—N1	118.96 (15)
C10—C11—C6	119.14 (15)	N2—C5—C4	123.01 (15)
C10—C11—C12	120.45 (15)	N1—C5—C4	118.02 (15)
C6—C11—C12	120.40 (15)	C2—C1—N1	120.65 (15)
O1—C6—C7	118.53 (15)	C2—C1—H1	119.7
O1—C6—C11	121.39 (15)	N1—C1—H1	119.7
C7—C6—C11	120.07 (15)	C5—N2—H1N2	117.4 (14)
C9—C10—C11	120.93 (15)	C5—N2—H2N2	118.5 (15)
C9—C10—H10	119.5	H1N2—N2—H2N2	124 (2)
C11—C10—H10	119.5	C5—N1—C1	122.29 (15)
C10—C9—C8	119.19 (16)	C5—N1—H1N	118.3 (14)
C10—C9—H9	120.4	C1—N1—H1N	119.2 (14)
C8—C9—H9	120.4	C4—C3—C2	120.04 (15)
O3—C12—O2	123.71 (16)	C4—C3—H3	120.0
O3—C12—C11	118.98 (15)	C2—C3—H3	120.0
O2—C12—C11	117.31 (15)	C1—C2—C3	118.94 (15)
C7—C8—C9	120.98 (17)	C1—C2—Br1	120.45 (12)
C7—C8—H8	119.5	C3—C2—Br1	120.58 (12)
C9—C8—H8	119.5	C3—C4—C5	120.05 (15)
C8—C7—C6	119.69 (16)	C3—C4—H4	120.0
C8—C7—H7	120.2	C5—C4—H4	120.0
C6—C7—H7	120.2
C10—C11—C6—O1	179.45 (15)	O1—C6—C7—C8	−179.66 (17)
C12—C11—C6—O1	0.9 (2)	C11—C6—C7—C8	−0.5 (3)
C10—C11—C6—C7	0.3 (2)	N2—C5—N1—C1	179.40 (15)
C12—C11—C6—C7	−178.24 (16)	C4—C5—N1—C1	0.2 (2)
C6—C11—C10—C9	0.2 (2)	C2—C1—N1—C5	−0.3 (2)
C12—C11—C10—C9	178.82 (16)	N1—C1—C2—C3	−0.5 (2)
C11—C10—C9—C8	−0.6 (3)	N1—C1—C2—Br1	−178.37 (12)
C10—C11—C12—O3	0.3 (2)	C4—C3—C2—C1	1.2 (3)
C6—C11—C12—O3	178.84 (15)	C4—C3—C2—Br1	179.13 (13)
C10—C11—C12—O2	−179.02 (15)	C2—C3—C4—C5	−1.3 (3)
C6—C11—C12—O2	−0.4 (2)	N2—C5—C4—C3	−178.60 (16)
C10—C9—C8—C7	0.4 (3)	N1—C5—C4—C3	0.5 (2)
C9—C8—C7—C6	0.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O2	0.89 (3)	1.66 (3)	2.500 (2)	157 (2)
N1—H1N···O3	0.96 (2)	1.66 (2)	2.611 (2)	172 (2)
N2—H1N2···O2	0.85 (3)	1.98 (2)	2.818 (2)	170 (2)
N2—H2N2···O1i	0.82 (2)	2.14 (2)	2.917 (2)	160 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯O2	0.89 (3)	1.66 (3)	2.500 (2)	157 (2)
N1—H1N⋯O3	0.96 (2)	1.66 (2)	2.611 (2)	172 (2)
N2—H1N2⋯O2	0.85 (3)	1.98 (2)	2.818 (2)	170 (2)
N2—H2N2⋯O1i	0.82 (2)	2.14 (2)	2.917 (2)	160 (2)

Symmetry code: (i) .