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

In the title molecular salt, C(5)H(6)ClN(2) (+)·C(7)H(6)NO(2) (-), the cations and anions are connected by cation-to-anion and anion-to-anion N-H⋯O hydrogen bonds into a three-dimensional network. The dihedral angle between the ring and the CO(2) group in the anion is 7.14 (7)°.

Related literature

For general background to chloro­pyridinium derivatives, see: Brahadeeswaran et al. (2006 ▶); Tomaru et al. (1991 ▶). For N—H⋯O hydrogen bonds, see: Blessing (1986 ▶); Brown (1976 ▶).

Experimental

Crystal data

C5H6ClN2 +·C7H6NO2 −

M = 265.70

Monoclinic,

a = 6.9879 (4) Å

b = 22.0074 (13) Å

c = 8.0554 (5) Å

β = 92.796 (1)°

V = 1237.33 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 293 K

0.20 × 0.19 × 0.18 mm

Data collection

Bruker APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.941, T max = 0.946

12108 measured reflections

3086 independent reflections

2642 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.112

S = 1.04

3086 reflections

179 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.31 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812043085/bt6844sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812043085/bt6844Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812043085/bt6844Isup3.cml

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

C5H6ClN2+·C7H6NO2−	F(000) = 552
Mr = 265.70	Dx = 1.426 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2642 reflections
a = 6.9879 (4) Å	θ = 1.9–28.4°
b = 22.0074 (13) Å	µ = 0.31 mm−1
c = 8.0554 (5) Å	T = 293 K
β = 92.796 (1)°	Block, white crystalline
V = 1237.33 (13) Å3	0.20 × 0.19 × 0.18 mm
Z = 4

Bruker APEXII area-detector diffractometer	3086 independent reflections
Radiation source: fine-focus sealed tube	2642 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
ω scan	θmax = 28.4°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −9→9
Tmin = 0.941, Tmax = 0.946	k = −29→29
12108 measured reflections	l = −10→10

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0572P)2 + 0.3359P] where P = (Fo2 + 2Fc2)/3
3086 reflections	(Δ/σ)max = 0.001
179 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.31 e Å−3

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
C2	0.3159 (2)	0.04218 (6)	0.77668 (17)	0.0407 (3)
C3	0.3355 (2)	0.09763 (7)	0.6908 (2)	0.0479 (3)
H3	0.2372	0.1261	0.6889	0.057*
C4	0.4987 (2)	0.10919 (7)	0.61093 (19)	0.0486 (4)
H4	0.5133	0.1460	0.5563	0.058*
C5	0.6448 (2)	0.06560 (7)	0.61107 (17)	0.0431 (3)
C6	0.6216 (2)	0.01208 (6)	0.69117 (17)	0.0406 (3)
H6	0.7173	−0.0173	0.6911	0.049*
C7	0.71327 (19)	0.12257 (6)	1.01810 (16)	0.0359 (3)
C8	0.71041 (18)	0.18462 (6)	0.94334 (16)	0.0346 (3)
C9	0.87870 (19)	0.21125 (6)	0.89231 (17)	0.0389 (3)
H9	0.9937	0.1902	0.9066	0.047*
C10	0.87784 (19)	0.26832 (6)	0.82089 (17)	0.0407 (3)
H10	0.9923	0.2854	0.7895	0.049*
C11	0.70654 (19)	0.30071 (6)	0.79533 (16)	0.0371 (3)
C12	0.5373 (2)	0.27406 (6)	0.84646 (18)	0.0412 (3)
H12	0.4219	0.2948	0.8311	0.049*
C13	0.54024 (19)	0.21735 (6)	0.91937 (17)	0.0390 (3)
H13	0.4264	0.2006	0.9533	0.047*
N1	0.45860 (17)	0.00142 (5)	0.77144 (14)	0.0385 (3)
H1	0.4461	−0.0329	0.8210	0.046*
N2	0.1643 (2)	0.02799 (7)	0.86228 (19)	0.0545 (4)
N3	0.7058 (2)	0.35808 (6)	0.72634 (18)	0.0477 (3)
O1	0.86491 (14)	0.09238 (5)	1.02101 (14)	0.0471 (3)
O2	0.55877 (14)	0.10303 (4)	1.07566 (14)	0.0483 (3)
Cl1	0.85224 (7)	0.07952 (2)	0.50832 (6)	0.06516 (16)
H3A	0.598 (3)	0.3696 (9)	0.680 (2)	0.049 (5)*
H2A	0.155 (3)	−0.0086 (11)	0.909 (2)	0.067 (6)*
H2B	0.078 (3)	0.0551 (10)	0.877 (3)	0.069 (6)*
H3B	0.808 (3)	0.3657 (9)	0.676 (3)	0.062 (5)*

	U11	U22	U33	U12	U13	U23
C2	0.0455 (7)	0.0342 (6)	0.0423 (7)	0.0007 (5)	0.0014 (5)	−0.0021 (5)
C3	0.0525 (8)	0.0348 (7)	0.0557 (8)	0.0043 (6)	−0.0035 (7)	0.0047 (6)
C4	0.0605 (9)	0.0358 (7)	0.0488 (8)	−0.0081 (6)	−0.0060 (7)	0.0091 (6)
C5	0.0458 (7)	0.0437 (7)	0.0395 (7)	−0.0108 (6)	−0.0008 (5)	0.0013 (6)
C6	0.0414 (7)	0.0371 (7)	0.0432 (7)	−0.0019 (5)	0.0007 (5)	−0.0009 (5)
C7	0.0370 (6)	0.0310 (6)	0.0397 (6)	0.0004 (5)	0.0026 (5)	−0.0017 (5)
C8	0.0366 (6)	0.0310 (6)	0.0364 (6)	−0.0006 (5)	0.0032 (5)	−0.0013 (5)
C9	0.0330 (6)	0.0389 (7)	0.0447 (7)	0.0017 (5)	0.0026 (5)	0.0013 (5)
C10	0.0349 (6)	0.0418 (7)	0.0457 (7)	−0.0061 (5)	0.0048 (5)	0.0027 (6)
C11	0.0417 (7)	0.0319 (6)	0.0377 (6)	−0.0027 (5)	0.0014 (5)	−0.0015 (5)
C12	0.0366 (7)	0.0360 (6)	0.0512 (8)	0.0044 (5)	0.0050 (6)	0.0026 (6)
C13	0.0346 (6)	0.0359 (6)	0.0470 (7)	−0.0019 (5)	0.0071 (5)	0.0008 (5)
N1	0.0444 (6)	0.0297 (5)	0.0414 (6)	−0.0003 (4)	0.0041 (5)	0.0025 (4)
N2	0.0529 (8)	0.0424 (7)	0.0698 (9)	0.0093 (6)	0.0199 (7)	0.0069 (6)
N3	0.0450 (7)	0.0381 (6)	0.0600 (8)	−0.0030 (5)	0.0026 (6)	0.0104 (6)
O1	0.0389 (5)	0.0374 (5)	0.0654 (7)	0.0055 (4)	0.0072 (5)	0.0045 (4)
O2	0.0403 (5)	0.0372 (5)	0.0686 (7)	0.0042 (4)	0.0144 (5)	0.0137 (5)
Cl1	0.0575 (3)	0.0704 (3)	0.0685 (3)	−0.0175 (2)	0.0128 (2)	0.0112 (2)

C2—N2	1.329 (2)	C8—C13	1.3956 (18)
C2—N1	1.3433 (18)	C9—C10	1.3814 (19)
C2—C3	1.413 (2)	C9—H9	0.9300
C3—C4	1.360 (2)	C10—C11	1.3997 (19)
C3—H3	0.9300	C10—H10	0.9300
C4—C5	1.401 (2)	C11—N3	1.3794 (18)
C4—H4	0.9300	C11—C12	1.3997 (19)
C5—C6	1.357 (2)	C12—C13	1.3791 (19)
C5—Cl1	1.7312 (15)	C12—H12	0.9300
C6—N1	1.3573 (17)	C13—H13	0.9300
C6—H6	0.9300	N1—H1	0.8600
C7—O1	1.2500 (16)	N2—H2A	0.89 (2)
C7—O2	1.2706 (16)	N2—H2B	0.86 (2)
C7—C8	1.4921 (18)	N3—H3A	0.862 (19)
C8—C9	1.3937 (18)	N3—H3B	0.86 (2)
N2—C2—N1	118.11 (13)	C8—C9—H9	119.4
N2—C2—C3	123.76 (14)	C9—C10—C11	120.70 (12)
N1—C2—C3	118.14 (13)	C9—C10—H10	119.6
C4—C3—C2	119.78 (14)	C11—C10—H10	119.6
C4—C3—H3	120.1	N3—C11—C10	120.77 (13)
C2—C3—H3	120.1	N3—C11—C12	121.04 (13)
C3—C4—C5	119.95 (13)	C10—C11—C12	118.16 (12)
C3—C4—H4	120.0	C13—C12—C11	120.62 (12)
C5—C4—H4	120.0	C13—C12—H12	119.7
C6—C5—C4	119.40 (14)	C11—C12—H12	119.7
C6—C5—Cl1	120.23 (12)	C12—C13—C8	121.38 (12)
C4—C5—Cl1	120.37 (11)	C12—C13—H13	119.3
C5—C6—N1	119.95 (13)	C8—C13—H13	119.3
C5—C6—H6	120.0	C2—N1—C6	122.74 (12)
N1—C6—H6	120.0	C2—N1—H1	118.6
O1—C7—O2	123.22 (12)	C6—N1—H1	118.6
O1—C7—C8	119.25 (12)	C2—N2—H2A	120.4 (13)
O2—C7—C8	117.53 (11)	C2—N2—H2B	119.4 (14)
C9—C8—C13	117.89 (12)	H2A—N2—H2B	120.1 (19)
C9—C8—C7	120.59 (12)	C11—N3—H3A	115.5 (12)
C13—C8—C7	121.51 (12)	C11—N3—H3B	112.7 (14)
C10—C9—C8	121.23 (12)	H3A—N3—H3B	117.8 (18)
C10—C9—H9	119.4
N2—C2—C3—C4	177.79 (15)	C7—C8—C9—C10	179.13 (12)
N1—C2—C3—C4	−2.3 (2)	C8—C9—C10—C11	−1.0 (2)
C2—C3—C4—C5	1.4 (2)	C9—C10—C11—N3	179.01 (13)
C3—C4—C5—C6	0.1 (2)	C9—C10—C11—C12	1.0 (2)
C3—C4—C5—Cl1	179.43 (12)	N3—C11—C12—C13	−178.26 (13)
C4—C5—C6—N1	−0.6 (2)	C10—C11—C12—C13	−0.2 (2)
Cl1—C5—C6—N1	−179.96 (10)	C11—C12—C13—C8	−0.5 (2)
O1—C7—C8—C9	−6.38 (19)	C9—C8—C13—C12	0.5 (2)
O2—C7—C8—C9	173.83 (12)	C7—C8—C13—C12	−178.37 (13)
O1—C7—C8—C13	172.44 (13)	N2—C2—N1—C6	−178.27 (13)
O2—C7—C8—C13	−7.35 (19)	C3—C2—N1—C6	1.8 (2)
C13—C8—C9—C10	0.3 (2)	C5—C6—N1—C2	−0.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.86	1.76	2.6135 (15)	175
N2—H2A···O1i	0.89 (2)	1.94 (2)	2.8216 (18)	172.1 (19)
N2—H2B···O1ii	0.86 (2)	2.10 (2)	2.8776 (17)	150.3 (19)
N3—H3A···O1iii	0.862 (19)	2.19 (2)	3.0357 (18)	167.4 (17)
N3—H3B···O2iv	0.86 (2)	2.08 (2)	2.9291 (18)	171 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.86	1.76	2.6135 (15)	175
N2—H2A⋯O1i	0.89 (2)	1.94 (2)	2.8216 (18)	172.1 (19)
N2—H2B⋯O1ii	0.86 (2)	2.10 (2)	2.8776 (17)	150.3 (19)
N3—H3A⋯O1iii	0.862 (19)	2.19 (2)	3.0357 (18)	167.4 (17)
N3—H3B⋯O2iv	0.86 (2)	2.08 (2)	2.9291 (18)	171 (2)

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