2-Amino-5-chloro-pyridinium 4-hydroxy-benzoate.

In the title salt, C(5)H(6)ClN(2) (+)·C(7)H(5)O(3) (-), the carboxyl-ate mean plane of the 4-hydroxy-benzoate anion is twisted by 7.16 (9)° from the attached ring. In the crystal structure, the cations and anions are linked via O-H⋯O and N-H⋯O hydrogen bonds, as well as C-H⋯O contacts, forming a three-dimensional network. In addition, weak π-π inter-actions involving the benzene and pyridinium rings, with centroid-to-centroid distances of 3.8941 (9) Å, are observed.

Related literature

For background to the chemistry of substituted pyridines, see: Pozharski et al. (1997 ▶); Katritzky et al. (1996 ▶). For related structures, see: Pourayoubi et al. (2007 ▶); Akriche & Rzaigui (2005 ▶); Janczak & Perpétuo (2009 ▶). For details of hydrogen bonding, see: Jeffrey & Saenger (1991 ▶); Jeffrey (1997 ▶); Scheiner (1997 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C5H6ClN2 +·C7H5O3 −

M = 266.68

Monoclinic,

a = 10.0893 (3) Å

b = 11.7612 (4) Å

c = 11.6634 (3) Å

β = 116.113 (2)°

V = 1242.74 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 100 K

0.69 × 0.20 × 0.14 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.814, T max = 0.958

12446 measured reflections

3630 independent reflections

2663 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.110

S = 1.04

3630 reflections

207 parameters

All H-atom parameters refined

Δρmax = 0.22 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/S1600536810004265/tk2625sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810004265/tk2625Isup2.hkl

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

C5H6ClN2+·C7H5O3−	F(000) = 552
Mr = 266.68	Dx = 1.425 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4875 reflections
a = 10.0893 (3) Å	θ = 2.3–29.9°
b = 11.7612 (4) Å	µ = 0.31 mm−1
c = 11.6634 (3) Å	T = 100 K
β = 116.113 (2)°	Block, colourless
V = 1242.74 (6) Å3	0.69 × 0.20 × 0.14 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	3630 independent reflections
Radiation source: fine-focus sealed tube	2663 reflections with I > 2σ(I)
graphite	Rint = 0.020
φ and ω scans	θmax = 30.1°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→14
Tmin = 0.814, Tmax = 0.958	k = −16→16
12446 measured reflections	l = −16→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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	All H-atom parameters refined
S = 1.04	w = 1/[σ2(Fo2) + (0.0478P)2 + 0.2067P] where P = (Fo2 + 2Fc2)/3
3630 reflections	(Δ/σ)max < 0.001
207 parameters	Δρmax = 0.22 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
Cl1	0.21064 (4)	0.98776 (4)	−0.17272 (4)	0.06226 (15)
N1	0.51321 (13)	0.78671 (10)	0.07645 (11)	0.0444 (3)
N2	0.63089 (16)	0.77385 (14)	0.29586 (13)	0.0574 (3)
C1	0.53134 (15)	0.82441 (12)	0.19187 (13)	0.0439 (3)
C2	0.44186 (16)	0.91497 (14)	0.19530 (14)	0.0510 (4)
C3	0.34358 (17)	0.96337 (14)	0.08507 (15)	0.0512 (4)
C4	0.33162 (14)	0.92372 (13)	−0.03259 (13)	0.0454 (3)
C5	0.41534 (15)	0.83516 (13)	−0.03444 (13)	0.0454 (3)
O1	0.00092 (13)	0.66336 (10)	0.45630 (11)	0.0579 (3)
O2	0.34526 (13)	1.11961 (9)	0.47186 (9)	0.0567 (3)
O3	0.22698 (11)	1.09176 (8)	0.26301 (8)	0.0463 (2)
C6	0.21056 (18)	0.92410 (14)	0.51840 (13)	0.0531 (4)
C7	0.14592 (19)	0.82697 (15)	0.53591 (13)	0.0563 (4)
C8	0.06192 (15)	0.75826 (12)	0.43312 (13)	0.0438 (3)
C9	0.04555 (15)	0.78713 (12)	0.31209 (12)	0.0426 (3)
C10	0.11107 (14)	0.88452 (12)	0.29507 (12)	0.0397 (3)
C11	0.19355 (14)	0.95522 (12)	0.39715 (11)	0.0392 (3)
C12	0.25875 (14)	1.06243 (12)	0.37582 (12)	0.0398 (3)
H2A	0.4538 (17)	0.9382 (14)	0.2769 (16)	0.059 (5)*
H3A	0.283 (2)	1.0251 (15)	0.0866 (17)	0.064 (5)*
H5A	0.4139 (17)	0.8021 (14)	−0.1096 (16)	0.060 (5)*
H6A	0.2676 (19)	0.9721 (15)	0.5889 (17)	0.065 (5)*
H7A	0.1571 (19)	0.8087 (16)	0.6168 (18)	0.068 (5)*
H9A	−0.0099 (17)	0.7369 (13)	0.2417 (15)	0.054 (4)*
H10A	0.1007 (16)	0.9043 (13)	0.2125 (15)	0.048 (4)*
H1O1	−0.053 (2)	0.6331 (17)	0.386 (2)	0.073 (6)*
H1N1	0.575 (2)	0.7250 (16)	0.0689 (18)	0.076 (6)*
H1N2	0.6509 (19)	0.8050 (16)	0.3681 (18)	0.062 (5)*
H2N2	0.689 (2)	0.7177 (19)	0.2877 (19)	0.080 (6)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0607 (2)	0.0623 (3)	0.0572 (2)	0.00938 (18)	0.01990 (18)	0.00670 (19)
N1	0.0523 (6)	0.0433 (6)	0.0410 (6)	0.0039 (5)	0.0235 (5)	−0.0053 (5)
N2	0.0729 (8)	0.0590 (9)	0.0403 (6)	0.0110 (7)	0.0249 (6)	−0.0023 (6)
C1	0.0515 (7)	0.0438 (7)	0.0425 (6)	−0.0042 (6)	0.0262 (6)	−0.0069 (6)
C2	0.0587 (8)	0.0536 (9)	0.0476 (7)	0.0000 (7)	0.0297 (6)	−0.0132 (7)
C3	0.0528 (7)	0.0479 (9)	0.0585 (8)	0.0037 (7)	0.0297 (7)	−0.0092 (7)
C4	0.0441 (6)	0.0451 (8)	0.0475 (7)	−0.0022 (6)	0.0206 (5)	−0.0043 (6)
C5	0.0504 (7)	0.0467 (8)	0.0416 (7)	0.0000 (6)	0.0226 (6)	−0.0071 (6)
O1	0.0716 (7)	0.0539 (7)	0.0450 (5)	−0.0210 (6)	0.0228 (5)	0.0014 (5)
O2	0.0799 (7)	0.0531 (6)	0.0401 (5)	−0.0245 (5)	0.0291 (5)	−0.0082 (5)
O3	0.0597 (5)	0.0440 (5)	0.0370 (4)	0.0000 (4)	0.0229 (4)	0.0042 (4)
C6	0.0709 (9)	0.0536 (9)	0.0333 (6)	−0.0166 (8)	0.0217 (6)	−0.0052 (6)
C7	0.0763 (10)	0.0591 (10)	0.0347 (6)	−0.0180 (8)	0.0256 (7)	0.0003 (7)
C8	0.0486 (7)	0.0423 (7)	0.0406 (6)	−0.0039 (6)	0.0197 (5)	0.0024 (6)
C9	0.0485 (6)	0.0418 (7)	0.0345 (6)	−0.0032 (6)	0.0155 (5)	−0.0028 (6)
C10	0.0466 (6)	0.0403 (7)	0.0329 (6)	0.0027 (6)	0.0181 (5)	0.0014 (5)
C11	0.0459 (6)	0.0384 (7)	0.0348 (6)	0.0000 (5)	0.0192 (5)	−0.0001 (5)
C12	0.0480 (6)	0.0380 (7)	0.0372 (6)	0.0018 (6)	0.0224 (5)	−0.0011 (5)

Cl1—C4	1.7241 (15)	O1—H1O1	0.83 (2)
N1—C1	1.3511 (17)	O2—C12	1.2682 (15)
N1—C5	1.3595 (18)	O3—C12	1.2577 (15)
N1—H1N1	0.99 (2)	C6—C7	1.375 (2)
N2—C1	1.3271 (19)	C6—C11	1.3963 (18)
N2—H1N2	0.858 (19)	C6—H6A	0.954 (18)
N2—H2N2	0.91 (2)	C7—C8	1.384 (2)
C1—C2	1.408 (2)	C7—H7A	0.925 (19)
C2—C3	1.356 (2)	C8—C9	1.3892 (19)
C2—H2A	0.946 (16)	C9—C10	1.3798 (19)
C3—C4	1.403 (2)	C9—H9A	0.965 (16)
C3—H3A	0.953 (18)	C10—C11	1.3889 (18)
C4—C5	1.347 (2)	C10—H10A	0.950 (15)
C5—H5A	0.953 (17)	C11—C12	1.4929 (19)
O1—C8	1.3581 (17)
C1—N1—C5	122.24 (12)	C7—C6—C11	120.90 (13)
C1—N1—H1N1	121.1 (11)	C7—C6—H6A	120.6 (11)
C5—N1—H1N1	116.5 (11)	C11—C6—H6A	118.5 (11)
C1—N2—H1N2	117.6 (12)	C6—C7—C8	120.42 (13)
C1—N2—H2N2	119.3 (13)	C6—C7—H7A	119.5 (11)
H1N2—N2—H2N2	121.8 (18)	C8—C7—H7A	120.1 (11)
N2—C1—N1	118.66 (13)	O1—C8—C7	117.77 (12)
N2—C1—C2	123.35 (13)	O1—C8—C9	122.79 (12)
N1—C1—C2	117.98 (13)	C7—C8—C9	119.43 (13)
C3—C2—C1	120.07 (13)	C10—C9—C8	119.92 (12)
C3—C2—H2A	123.3 (10)	C10—C9—H9A	121.4 (10)
C1—C2—H2A	116.6 (10)	C8—C9—H9A	118.7 (10)
C2—C3—C4	120.00 (14)	C9—C10—C11	121.19 (12)
C2—C3—H3A	120.6 (11)	C9—C10—H10A	120.2 (9)
C4—C3—H3A	119.4 (11)	C11—C10—H10A	118.7 (9)
C5—C4—C3	119.20 (13)	C10—C11—C6	118.13 (13)
C5—C4—Cl1	120.66 (11)	C10—C11—C12	120.30 (11)
C3—C4—Cl1	120.14 (11)	C6—C11—C12	121.56 (12)
C4—C5—N1	120.45 (13)	O3—C12—O2	122.55 (12)
C4—C5—H5A	125.1 (10)	O3—C12—C11	118.55 (11)
N1—C5—H5A	114.5 (10)	O2—C12—C11	118.89 (11)
C8—O1—H1O1	108.3 (14)
C5—N1—C1—N2	−178.89 (13)	C6—C7—C8—C9	1.2 (2)
C5—N1—C1—C2	1.8 (2)	O1—C8—C9—C10	−179.65 (13)
N2—C1—C2—C3	179.25 (15)	C7—C8—C9—C10	−0.9 (2)
N1—C1—C2—C3	−1.5 (2)	C8—C9—C10—C11	−0.2 (2)
C1—C2—C3—C4	−0.4 (2)	C9—C10—C11—C6	1.0 (2)
C2—C3—C4—C5	2.1 (2)	C9—C10—C11—C12	−177.69 (12)
C2—C3—C4—Cl1	−178.10 (12)	C7—C6—C11—C10	−0.8 (2)
C3—C4—C5—N1	−1.8 (2)	C7—C6—C11—C12	177.90 (15)
Cl1—C4—C5—N1	178.38 (11)	C10—C11—C12—O3	5.95 (19)
C1—N1—C5—C4	−0.2 (2)	C6—C11—C12—O3	−172.73 (13)
C11—C6—C7—C8	−0.3 (3)	C10—C11—C12—O2	−173.19 (12)
C6—C7—C8—O1	179.94 (15)	C6—C11—C12—O2	8.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O3i	0.84 (2)	1.91 (2)	2.7132 (15)	160 (2)
N1—H1N1···O2ii	0.99 (2)	1.66 (2)	2.6320 (18)	169.2 (18)
N2—H1N2···O2iii	0.857 (19)	2.051 (19)	2.8972 (18)	169 (2)
N2—H2N2···O3ii	0.92 (2)	1.93 (2)	2.825 (2)	167 (2)
C3—H3A···O3	0.95 (2)	2.488 (19)	3.181 (2)	129.5 (14)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯O3i	0.84 (2)	1.91 (2)	2.7132 (15)	160 (2)
N1—H1N1⋯O2ii	0.99 (2)	1.66 (2)	2.6320 (18)	169.2 (18)
N2—H1N2⋯O2iii	0.857 (19)	2.051 (19)	2.8972 (18)	169 (2)
N2—H2N2⋯O3ii	0.92 (2)	1.93 (2)	2.825 (2)	167 (2)
C3—H3A⋯O3	0.95 (2)	2.488 (19)	3.181 (2)	129.5 (14)

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