2-Amino-5-chloro-pyridinium salicylate.

In the crystal structure of the title salt, C(5)H(6)ClN(2) (+)·C(7)H(5)O(3) (-), the protonated N atom and the 2-amino group of the cation are hydrogen bonded to the carboxyl-ate O atoms via a pair of N-H⋯O hydrogen bonds, forming R(2) (2)(8) ring motifs. These motifs are centrosymmetrically paired via N-H⋯O hydrogen bonds, forming a complementary donor-donor-acceptor-acceptor (DDAA) array. A typical intra-molecular O-H⋯O hydrogen bond is also observed in the salicylate anion. The crystal structure is further stabilized by weak C-H⋯π inter-actions.

Related literature

For 2-amino­pyridines, see: Gellert & Hsu (1988 ▶); Banerjee & Murugavel (2004 ▶); Bis & Zaworotko (2005 ▶); Bis et al. (2006 ▶) and for salicylic acid, see: Cochran (1953 ▶); Singh & Vijayan (1974 ▶); Varughese & Kartha (1982 ▶). For related structures, see: Hemamalini & Fun (2010a ▶,b ▶,c ▶). Pourayoubi et al. (2007 ▶). For n class="Chemical">hydrogen-bond motifs, see: Bernstein et al. (1995 ▶) and for hydrogen-bonding patterns in organic salts, see: Baskar Raj et al. (2003 ▶). 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

C5H6ClN2 +·n class="Chemical">C7H5O3 −

M = 266.68

Monoclinic,

a = 6.7403 (6) Å

b = 14.5574 (12) Å

c = 13.2857 (9) Å

β = 115.550 (4)°

V = 1176.13 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.33 mm−1

T = 100 K

0.38 × 0.34 × 0.23 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.887, T max = 0.929

19132 measured reflections

5144 independent reflections

4405 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.124

S = 1.17

5144 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.66 e Å−3

Δρmin = −0.43 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/S1600536810018210/sj5004sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810018210/sj5004Isup2.hkl

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

C5H6ClN2+·C7H5O3−	F(000) = 552
Mr = 266.68	Dx = 1.506 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8071 reflections
a = 6.7403 (6) Å	θ = 2.8–35.0°
b = 14.5574 (12) Å	µ = 0.33 mm−1
c = 13.2857 (9) Å	T = 100 K
β = 115.550 (4)°	Block, colourless
V = 1176.13 (16) Å3	0.38 × 0.34 × 0.23 mm
Z = 4

Bruker APEXII DUO CCD area-detector diffractometer	5144 independent reflections
Radiation source: fine-focus sealed tube	4405 reflections with I > 2σ(I)
graphite	Rint = 0.026
φ and ω scans	θmax = 35.1°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→9
Tmin = 0.887, Tmax = 0.929	k = −23→23
19132 measured reflections	l = −21→21

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H-atom parameters constrained
S = 1.17	w = 1/[σ2(Fo2) + (0.0671P)2 + 0.2275P] where P = (Fo2 + 2Fc2)/3
5144 reflections	(Δ/σ)max = 0.001
164 parameters	Δρmax = 0.66 e Å−3
0 restraints	Δρmin = −0.43 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
Cl1	−0.19050 (4)	0.904645 (18)	0.14133 (2)	0.02103 (8)
N1	0.41620 (13)	0.90963 (5)	0.37992 (7)	0.01402 (14)
H1	0.4827	0.8888	0.4469	0.017*
N2	0.74627 (14)	0.97248 (6)	0.40024 (7)	0.01929 (16)
H2A	0.8072	0.9514	0.4672	0.023*
H2B	0.8229	1.0030	0.3741	0.023*
C1	0.19743 (15)	0.89260 (6)	0.32167 (8)	0.01479 (15)
H1A	0.1225	0.8595	0.3544	0.018*
C2	0.08837 (15)	0.92433 (7)	0.21489 (7)	0.01471 (15)
C3	0.20331 (15)	0.97455 (7)	0.16657 (7)	0.01588 (15)
H3	0.1298	0.9965	0.0940	0.019*
C4	0.42261 (15)	0.99101 (7)	0.22608 (7)	0.01550 (15)
H4	0.4992	1.0238	0.1941	0.019*
C5	0.53371 (15)	0.95784 (6)	0.33713 (7)	0.01379 (15)
O1	0.56169 (12)	0.72179 (6)	0.25181 (6)	0.01955 (15)
H1B	0.5299	0.7070	0.1871	0.029*
O2	0.62190 (11)	0.65244 (5)	0.09104 (6)	0.01729 (14)
O3	0.95143 (13)	0.59845 (5)	0.11872 (6)	0.01772 (14)
C7	0.77978 (15)	0.70954 (6)	0.31440 (7)	0.01377 (15)
C8	0.86682 (17)	0.73401 (7)	0.42726 (8)	0.01670 (16)
H8	0.7754	0.7583	0.4567	0.020*
C9	1.08961 (17)	0.72202 (7)	0.49541 (8)	0.01810 (17)
H9	1.1464	0.7380	0.5704	0.022*
C10	1.22897 (16)	0.68615 (7)	0.45190 (8)	0.01796 (17)
H10	1.3782	0.6787	0.4975	0.022*
C11	1.14261 (15)	0.66179 (6)	0.34034 (8)	0.01524 (15)
H11	1.2353	0.6382	0.3113	0.018*
C12	0.91805 (14)	0.67199 (6)	0.27039 (7)	0.01249 (14)
C13	0.82718 (15)	0.63875 (6)	0.15205 (7)	0.01318 (15)

	U11	U22	U33	U12	U13	U23
Cl1	0.01164 (11)	0.02568 (13)	0.02128 (12)	−0.00140 (7)	0.00287 (8)	−0.00279 (8)
N1	0.0125 (3)	0.0153 (3)	0.0128 (3)	−0.0010 (2)	0.0041 (2)	0.0018 (2)
N2	0.0127 (3)	0.0256 (4)	0.0160 (3)	−0.0046 (3)	0.0029 (3)	0.0045 (3)
C1	0.0129 (3)	0.0144 (4)	0.0164 (4)	−0.0011 (3)	0.0057 (3)	−0.0001 (3)
C2	0.0116 (3)	0.0160 (4)	0.0147 (3)	−0.0002 (3)	0.0039 (3)	−0.0016 (3)
C3	0.0148 (4)	0.0178 (4)	0.0127 (3)	0.0013 (3)	0.0038 (3)	0.0009 (3)
C4	0.0150 (4)	0.0173 (4)	0.0136 (3)	−0.0003 (3)	0.0056 (3)	0.0025 (3)
C5	0.0122 (3)	0.0149 (4)	0.0131 (3)	−0.0006 (3)	0.0044 (3)	0.0007 (3)
O1	0.0123 (3)	0.0292 (4)	0.0164 (3)	0.0026 (2)	0.0054 (2)	−0.0033 (3)
O2	0.0128 (3)	0.0237 (3)	0.0128 (3)	0.0018 (2)	0.0031 (2)	−0.0024 (2)
O3	0.0176 (3)	0.0215 (3)	0.0145 (3)	0.0046 (2)	0.0074 (3)	−0.0015 (2)
C7	0.0133 (3)	0.0146 (3)	0.0134 (3)	−0.0001 (3)	0.0057 (3)	−0.0004 (3)
C8	0.0184 (4)	0.0189 (4)	0.0139 (3)	0.0001 (3)	0.0079 (3)	−0.0016 (3)
C9	0.0209 (4)	0.0187 (4)	0.0117 (3)	−0.0012 (3)	0.0042 (3)	−0.0008 (3)
C10	0.0158 (4)	0.0181 (4)	0.0150 (4)	0.0010 (3)	0.0019 (3)	0.0000 (3)
C11	0.0133 (3)	0.0153 (4)	0.0155 (3)	0.0012 (3)	0.0047 (3)	−0.0005 (3)
C12	0.0123 (3)	0.0130 (3)	0.0116 (3)	0.0004 (3)	0.0047 (3)	−0.0001 (3)
C13	0.0138 (3)	0.0135 (3)	0.0118 (3)	0.0004 (3)	0.0052 (3)	0.0004 (3)

Cl1—C2	1.7280 (9)	O1—H1B	0.8200
N1—C5	1.3534 (12)	O2—C13	1.2821 (11)
N1—C1	1.3603 (12)	O3—C13	1.2496 (11)
N1—H1	0.8600	C7—C8	1.4002 (13)
N2—C5	1.3285 (12)	C7—C12	1.4069 (12)
N2—H2A	0.8600	C8—C9	1.3901 (14)
N2—H2B	0.8600	C8—H8	0.9300
C1—C2	1.3662 (13)	C9—C10	1.3992 (14)
C1—H1A	0.9300	C9—H9	0.9300
C2—C3	1.4057 (13)	C10—C11	1.3846 (13)
C3—C4	1.3635 (13)	C10—H10	0.9300
C3—H3	0.9300	C11—C12	1.4012 (13)
C4—C5	1.4204 (12)	C11—H11	0.9300
C4—H4	0.9300	C12—C13	1.5001 (12)
O1—C7	1.3527 (11)
C5—N1—C1	122.87 (8)	O1—C7—C8	117.84 (8)
C5—N1—H1	118.6	O1—C7—C12	122.33 (8)
C1—N1—H1	118.6	C8—C7—C12	119.81 (8)
C5—N2—H2A	120.0	C9—C8—C7	120.10 (8)
C5—N2—H2B	120.0	C9—C8—H8	119.9
H2A—N2—H2B	120.0	C7—C8—H8	119.9
N1—C1—C2	119.66 (8)	C8—C9—C10	120.45 (8)
N1—C1—H1A	120.2	C8—C9—H9	119.8
C2—C1—H1A	120.2	C10—C9—H9	119.8
C1—C2—C3	119.63 (8)	C11—C10—C9	119.39 (9)
C1—C2—Cl1	119.87 (7)	C11—C10—H10	120.3
C3—C2—Cl1	120.48 (7)	C9—C10—H10	120.3
C4—C3—C2	119.98 (8)	C10—C11—C12	121.20 (8)
C4—C3—H3	120.0	C10—C11—H11	119.4
C2—C3—H3	120.0	C12—C11—H11	119.4
C3—C4—C5	119.78 (8)	C11—C12—C7	119.03 (8)
C3—C4—H4	120.1	C11—C12—C13	119.80 (8)
C5—C4—H4	120.1	C7—C12—C13	121.11 (8)
N2—C5—N1	119.03 (8)	O3—C13—O2	123.67 (8)
N2—C5—C4	122.89 (8)	O3—C13—C12	119.32 (8)
N1—C5—C4	118.08 (8)	O2—C13—C12	117.00 (7)
C7—O1—H1B	109.5
C5—N1—C1—C2	0.46 (14)	C8—C9—C10—C11	−0.61 (15)
N1—C1—C2—C3	−0.25 (14)	C9—C10—C11—C12	−0.31 (15)
N1—C1—C2—Cl1	−178.88 (7)	C10—C11—C12—C7	1.35 (14)
C1—C2—C3—C4	0.27 (14)	C10—C11—C12—C13	−175.67 (9)
Cl1—C2—C3—C4	178.89 (7)	O1—C7—C12—C11	179.72 (8)
C2—C3—C4—C5	−0.47 (14)	C8—C7—C12—C11	−1.48 (13)
C1—N1—C5—N2	179.07 (9)	O1—C7—C12—C13	−3.30 (14)
C1—N1—C5—C4	−0.64 (13)	C8—C7—C12—C13	175.51 (8)
C3—C4—C5—N2	−179.05 (9)	C11—C12—C13—O3	3.25 (13)
C3—C4—C5—N1	0.64 (13)	C7—C12—C13—O3	−173.71 (8)
O1—C7—C8—C9	179.44 (9)	C11—C12—C13—O2	−177.95 (8)
C12—C7—C8—C9	0.58 (14)	C7—C12—C13—O2	5.09 (13)
C7—C8—C9—C10	0.47 (15)

Cg1 is the centroid of the C7–C12 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.86	1.83	2.6928 (10)	178
O1—H1B···O2	0.82	1.82	2.5483 (11)	147
N2—H2A···O3i	0.86	1.96	2.8181 (11)	178
N2—H2B···O3ii	0.86	2.03	2.8321 (13)	154
C1—H1A···Cg1iii	0.93	2.57	3.3680 (11)	144

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C7–C12 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.86	1.83	2.6928 (10)	178
O1—H1B⋯O2	0.82	1.82	2.5483 (11)	147
N2—H2A⋯O3i	0.86	1.96	2.8181 (11)	178
N2—H2B⋯O3ii	0.86	2.03	2.8321 (13)	154
C1—H1A⋯Cg1iii	0.93	2.57	3.3680 (11)	144

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