2-Amino-5-chloro-pyridinium hydrogen succinate.

In the title salt, C(5)H(6)ClN(2) (+)·C(4)H(5)O(4) (-), the pyridine N atom is protonated. The pyridinium and amino groups associate via a pair of N-H⋯O hydrogen bonds to the carboxyl-ate O atoms of the singly deprotonated succinate anion. The hydrogen succinate anions self-assemble via O-H⋯O hydrogen bonds into chains along the b axis. The crystal structure is further stabilized by additional N-H⋯O hydrogen bonds involving the second amino H atoms, as well as C-H⋯O contacts, forming a three-dimensional network.

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 ▶); Zaouali Zgolli et al. (2009 ▶). For the structure of succinic acid, see: Gopalan et al. (2000 ▶); Leviel et al. (1981 ▶). For applications of succinic acid, see: Sauer et al. (2008 ▶); Song & Lee (2006 ▶); Zeikus et al. (1999 ▶)·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 +·C4H5O4 −

M = 246.65

Orthorhombic,

a = 5.2263 (1) Å

b = 13.5997 (3) Å

c = 14.9019 (3) Å

V = 1059.17 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.36 mm−1

T = 100 K

0.41 × 0.15 × 0.10 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.866, T max = 0.965

11594 measured reflections

3934 independent reflections

3581 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.082

S = 1.02

3934 reflections

189 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.27 e Å−3

Absolute structure: Flack (1983 ▶), 1604 Friedel pairs

Flack parameter: 0.05 (5)

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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810002990/tk2616sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810002990/tk2616Isup2.hkl

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

C5H6ClN2+·C4H5O4−	F(000) = 512
Mr = 246.65	Dx = 1.547 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3633 reflections
a = 5.2263 (1) Å	θ = 2.7–33.2°
b = 13.5997 (3) Å	µ = 0.36 mm−1
c = 14.9019 (3) Å	T = 100 K
V = 1059.17 (4) Å3	Blcok, yellow
Z = 4	0.41 × 0.15 × 0.10 mm

Bruker SMART APEXII CCD area-detector diffractometer	3934 independent reflections
Radiation source: fine-focus sealed tube	3581 reflections with I > 2σ(I)
graphite	Rint = 0.033
φ and ω scans	θmax = 33.2°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→6
Tmin = 0.866, Tmax = 0.965	k = −17→20
11594 measured reflections	l = −21→22

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)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.082	w = 1/[σ2(Fo2) + (0.0404P)2 + 0.0588P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
3934 reflections	Δρmax = 0.33 e Å−3
189 parameters	Δρmin = −0.27 e Å−3
0 restraints	Absolute structure: Flack (1983), 1604 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.05 (5)

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
Cl1	−0.16471 (6)	0.66417 (3)	0.01385 (3)	0.02344 (8)
N1	0.3976 (2)	0.47974 (9)	−0.04334 (8)	0.0152 (2)
N2	0.5510 (2)	0.33552 (9)	0.01762 (9)	0.0194 (2)
C1	0.3838 (2)	0.40861 (10)	0.02044 (9)	0.0152 (2)
C2	0.1897 (3)	0.41668 (10)	0.08661 (9)	0.0170 (2)
C3	0.0245 (3)	0.49419 (11)	0.08409 (10)	0.0183 (3)
C4	0.0469 (2)	0.56603 (10)	0.01630 (10)	0.0180 (2)
C5	0.2340 (3)	0.55775 (10)	−0.04688 (10)	0.0168 (2)
O1	0.42571 (19)	0.16607 (8)	0.11491 (6)	0.0208 (2)
O2	0.24386 (19)	0.03548 (7)	0.17729 (7)	0.0184 (2)
O3	0.8289 (2)	0.36179 (8)	0.25630 (8)	0.0232 (2)
O4	0.4478 (2)	0.29887 (8)	0.29328 (8)	0.0277 (3)
C6	0.4118 (2)	0.10302 (9)	0.17571 (9)	0.0142 (2)
C7	0.6061 (3)	0.10441 (10)	0.25145 (10)	0.0179 (3)
C8	0.7907 (2)	0.19017 (10)	0.24860 (10)	0.0181 (3)
C9	0.6663 (3)	0.28792 (10)	0.26836 (8)	0.0158 (2)
H2	0.180 (3)	0.3686 (13)	0.1322 (11)	0.020 (4)*
H3	−0.110 (3)	0.4991 (12)	0.1279 (11)	0.020 (4)*
H5	0.262 (3)	0.6021 (12)	−0.0964 (12)	0.016 (4)*
H7A	0.713 (4)	0.0395 (14)	0.2466 (13)	0.029 (5)*
H7B	0.504 (4)	0.1041 (13)	0.3078 (13)	0.033 (5)*
H8A	0.925 (4)	0.1818 (13)	0.2917 (12)	0.026 (5)*
H8B	0.883 (4)	0.1978 (13)	0.1893 (12)	0.023 (5)*
H1O3	0.764 (4)	0.4144 (14)	0.2709 (13)	0.026 (5)*
H1N1	0.517 (4)	0.4729 (13)	−0.0823 (13)	0.026 (5)*
H1N2	0.667 (4)	0.3364 (14)	−0.0209 (13)	0.029 (5)*
H2N2	0.538 (4)	0.2904 (14)	0.0544 (13)	0.027 (5)*

	U11	U22	U33	U12	U13	U23
Cl1	0.01978 (14)	0.01782 (15)	0.03271 (18)	0.00423 (12)	0.00071 (13)	−0.00177 (14)
N1	0.0162 (5)	0.0134 (5)	0.0162 (5)	−0.0010 (4)	0.0012 (4)	0.0015 (4)
N2	0.0200 (5)	0.0154 (5)	0.0227 (6)	0.0009 (5)	0.0046 (5)	0.0071 (5)
C1	0.0156 (5)	0.0133 (5)	0.0168 (6)	−0.0035 (4)	−0.0024 (4)	0.0009 (5)
C2	0.0188 (6)	0.0168 (6)	0.0154 (6)	−0.0038 (5)	0.0007 (5)	0.0013 (5)
C3	0.0177 (6)	0.0193 (6)	0.0180 (6)	−0.0033 (5)	0.0013 (5)	−0.0030 (5)
C4	0.0176 (5)	0.0154 (6)	0.0209 (6)	0.0001 (5)	−0.0026 (5)	−0.0021 (5)
C5	0.0175 (5)	0.0124 (6)	0.0205 (7)	−0.0014 (5)	−0.0030 (5)	0.0008 (5)
O1	0.0257 (5)	0.0174 (5)	0.0194 (5)	−0.0048 (4)	−0.0037 (4)	0.0068 (4)
O2	0.0197 (4)	0.0132 (4)	0.0222 (5)	−0.0027 (4)	−0.0035 (4)	0.0039 (4)
O3	0.0242 (5)	0.0129 (5)	0.0326 (6)	−0.0011 (4)	0.0082 (5)	−0.0048 (4)
O4	0.0192 (5)	0.0251 (6)	0.0387 (6)	−0.0001 (4)	0.0062 (4)	−0.0112 (5)
C6	0.0153 (5)	0.0118 (5)	0.0154 (6)	0.0024 (4)	0.0000 (4)	−0.0013 (5)
C7	0.0226 (6)	0.0140 (6)	0.0169 (6)	−0.0011 (5)	−0.0027 (5)	0.0027 (5)
C8	0.0169 (6)	0.0156 (6)	0.0218 (7)	0.0014 (5)	−0.0023 (5)	−0.0016 (5)
C9	0.0184 (5)	0.0153 (6)	0.0138 (6)	0.0011 (5)	−0.0014 (5)	−0.0017 (5)

Cl1—C4	1.7336 (13)	C5—H5	0.965 (17)
N1—C1	1.3580 (17)	O1—C6	1.2496 (16)
N1—C5	1.3636 (18)	O2—C6	1.2708 (16)
N1—H1N1	0.86 (2)	O3—C9	1.3281 (17)
N2—C1	1.3242 (17)	O3—H1O3	0.822 (19)
N2—H1N2	0.83 (2)	O4—C9	1.2100 (17)
N2—H2N2	0.83 (2)	C6—C7	1.5183 (19)
C1—C2	1.4189 (18)	C7—C8	1.5141 (19)
C2—C3	1.363 (2)	C7—H7A	1.047 (19)
C2—H2	0.944 (18)	C7—H7B	0.99 (2)
C3—C4	1.410 (2)	C8—C9	1.5090 (19)
C3—H3	0.961 (17)	C8—H8A	0.959 (19)
C4—C5	1.362 (2)	C8—H8B	1.010 (18)
C1—N1—C5	123.22 (12)	N1—C5—H5	115.0 (10)
C1—N1—H1N1	115.7 (12)	C9—O3—H1O3	110.9 (14)
C5—N1—H1N1	121.0 (12)	O1—C6—O2	123.33 (12)
C1—N2—H1N2	119.3 (14)	O1—C6—C7	119.44 (11)
C1—N2—H2N2	118.7 (13)	O2—C6—C7	117.21 (11)
H1N2—N2—H2N2	122.0 (19)	C8—C7—C6	114.51 (11)
N2—C1—N1	118.52 (12)	C8—C7—H7A	107.9 (10)
N2—C1—C2	123.49 (12)	C6—C7—H7A	107.2 (10)
N1—C1—C2	117.99 (12)	C8—C7—H7B	111.6 (11)
C3—C2—C1	119.57 (13)	C6—C7—H7B	105.6 (12)
C3—C2—H2	121.4 (11)	H7A—C7—H7B	109.9 (15)
C1—C2—H2	119.0 (11)	C9—C8—C7	113.48 (11)
C2—C3—C4	120.21 (13)	C9—C8—H8A	106.9 (11)
C2—C3—H3	119.8 (10)	C7—C8—H8A	110.9 (11)
C4—C3—H3	119.9 (10)	C9—C8—H8B	106.5 (10)
C5—C4—C3	119.81 (12)	C7—C8—H8B	114.0 (10)
C5—C4—Cl1	120.47 (11)	H8A—C8—H8B	104.4 (14)
C3—C4—Cl1	119.71 (11)	O4—C9—O3	123.52 (13)
C4—C5—N1	119.20 (13)	O4—C9—C8	125.11 (13)
C4—C5—H5	125.8 (10)	O3—C9—C8	111.36 (12)
C5—N1—C1—N2	179.59 (12)	Cl1—C4—C5—N1	−179.96 (10)
C5—N1—C1—C2	−0.30 (18)	C1—N1—C5—C4	0.21 (19)
N2—C1—C2—C3	−179.60 (13)	O1—C6—C7—C8	4.56 (19)
N1—C1—C2—C3	0.29 (18)	O2—C6—C7—C8	−176.50 (12)
C1—C2—C3—C4	−0.2 (2)	C6—C7—C8—C9	69.12 (16)
C2—C3—C4—C5	0.1 (2)	C7—C8—C9—O4	7.3 (2)
C2—C3—C4—Cl1	179.95 (11)	C7—C8—C9—O3	−173.70 (12)
C3—C4—C5—N1	−0.10 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1O3···O2i	0.821 (19)	1.819 (19)	2.5891 (15)	156 (2)
N1—H1N1···O2ii	0.86 (2)	1.85 (2)	2.7023 (15)	172.4 (19)
N2—H1N2···O1ii	0.84 (2)	1.95 (2)	2.7814 (15)	177 (2)
N2—H2N2···O1	0.826 (19)	2.004 (19)	2.8002 (16)	162 (2)
C5—H5···O4iii	0.964 (17)	2.391 (17)	3.2216 (18)	144.0 (13)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H1O3⋯O2i	0.821 (19)	1.819 (19)	2.5891 (15)	156 (2)
N1—H1N1⋯O2ii	0.86 (2)	1.85 (2)	2.7023 (15)	172.4 (19)
N2—H1N2⋯O1ii	0.84 (2)	1.95 (2)	2.7814 (15)	177 (2)
N2—H2N2⋯O1	0.826 (19)	2.004 (19)	2.8002 (16)	162 (2)
C5—H5⋯O4iii	0.964 (17)	2.391 (17)	3.2216 (18)	144.0 (13)

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