4-Amino-pyridinium 4-carb-oxy-butano-ate.

The asymmetric unit of the title salt, C(5)H(7)N(2) (+)·C(5)H(7)O(4) (-), contains two 4-amino-pyridinium cations and two 4-carb-oxy-butano-ate anions. Each 4-amino-pyridinium cation is planar, with a maximum deviation of 0.005 (2) Å. Both 4-carb-oxy-butano-ate anions adopt an extended conformation. In the crystal structure, the cations and anions are linked via N-H⋯O, O-H⋯O and C-H⋯O hydrogen bonds, forming a two-dimensional network parallel to the bc plane.

Related literature

For the biological activity of 4-amino­pyridine, see: Schwid et al. (1997 ▶). For crystal structure determinations of 4-amino­pyridine, see: Chao & Schempp (1977 ▶); Anderson et al. (2005 ▶). For conformations of 4-carb­oxy­butano­ate (hydrogen glutarate) anions, see: Saraswathi et al. (2001 ▶).

Experimental

Crystal data

C5H7N2 +·C5H7O4 −

M = 226.23

Monoclinic,

a = 9.6159 (2) Å

b = 10.3065 (2) Å

c = 22.6801 (5) Å

β = 102.143 (1)°

V = 2197.45 (8) Å3

Z = 8

Mo Kα radiation

μ = 0.11 mm−1

T = 296 K

0.35 × 0.26 × 0.21 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.963, T max = 0.978

7931 measured reflections

7931 independent reflections

5556 reflections with I > 2σ(I)

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.154

S = 1.04

7931 reflections

290 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.20 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/S1600536810028734/wn2401sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810028734/wn2401Isup2.hkl

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

C5H7N2+·C5H7O4−	F(000) = 960
Mr = 226.23	Dx = 1.368 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8906 reflections
a = 9.6159 (2) Å	θ = 2.5–30.1°
b = 10.3065 (2) Å	µ = 0.11 mm−1
c = 22.6801 (5) Å	T = 296 K
β = 102.143 (1)°	Block, colourless
V = 2197.45 (8) Å3	0.35 × 0.26 × 0.21 mm
Z = 8

Bruker SMART APEXII CCD area-detector diffractometer	7931 independent reflections
Radiation source: fine-focus sealed tube	5556 reflections with I > 2σ(I)
graphite	Rint = 0.0000
φ and ω scans	θmax = 32.6°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −14→14
Tmin = 0.963, Tmax = 0.978	k = −15→15
7931 measured reflections	l = −11→34

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0758P)2 + 0.2205P] where P = (Fo2 + 2Fc2)/3
7931 reflections	(Δ/σ)max < 0.001
290 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

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
O1A	0.28193 (16)	1.02435 (13)	0.06872 (6)	0.0516 (3)
H1O1	0.2530	1.0161	0.0289	0.077*
O2A	0.41099 (16)	0.95000 (13)	0.15319 (5)	0.0478 (3)
O3A	0.76925 (16)	0.49292 (13)	0.05256 (5)	0.0528 (4)
O4A	0.74003 (16)	0.55719 (12)	0.14167 (5)	0.0454 (3)
C1A	0.3787 (2)	0.94695 (15)	0.09826 (7)	0.0352 (3)
C2A	0.4485 (2)	0.85513 (16)	0.06135 (7)	0.0370 (3)
H2AA	0.5028	0.9059	0.0381	0.044*
H2AB	0.3745	0.8103	0.0330	0.044*
C3A	0.5465 (2)	0.75453 (16)	0.09724 (7)	0.0352 (3)
H3AA	0.6264	0.7976	0.1230	0.042*
H3AB	0.4955	0.7064	0.1227	0.042*
C4A	0.60070 (19)	0.66165 (16)	0.05536 (7)	0.0366 (3)
H4AA	0.5202	0.6144	0.0322	0.044*
H4AB	0.6415	0.7121	0.0271	0.044*
C5A	0.7105 (2)	0.56458 (15)	0.08576 (7)	0.0346 (3)
N1A	0.28175 (17)	0.87243 (15)	0.83697 (7)	0.0449 (4)
H1AA	0.2264	0.9279	0.8486	0.054*
N2A	0.53978 (18)	0.60387 (16)	0.78136 (7)	0.0499 (4)
H2AC	0.5341	0.5918	0.7434	0.060*
H2AD	0.5987	0.5590	0.8072	0.060*
C6A	0.3744 (2)	0.80430 (19)	0.87789 (8)	0.0488 (4)
H6AA	0.3778	0.8191	0.9186	0.059*
C7A	0.4634 (2)	0.71465 (18)	0.86214 (8)	0.0461 (4)
H7AA	0.5268	0.6692	0.8915	0.055*
C8A	0.45783 (19)	0.69135 (17)	0.79991 (8)	0.0379 (3)
C9A	0.3609 (2)	0.76547 (17)	0.75810 (7)	0.0399 (4)
H9AA	0.3548	0.7543	0.7169	0.048*
C10A	0.2754 (2)	0.85416 (19)	0.77826 (8)	0.0434 (4)
H10A	0.2115	0.9027	0.7504	0.052*
O1B	1.22169 (16)	−0.01002 (13)	0.95900 (5)	0.0527 (4)
O2B	1.10552 (17)	0.05354 (13)	0.86994 (5)	0.0494 (3)
O3B	0.72084 (16)	0.52422 (13)	0.94174 (6)	0.0532 (4)
H1O3	0.7347	0.5145	0.9828	0.080*
O4B	0.76125 (17)	0.44368 (13)	0.85744 (5)	0.0524 (3)
C1B	1.12988 (19)	0.06276 (15)	0.92524 (7)	0.0359 (3)
C2B	1.05243 (19)	0.16092 (15)	0.95600 (7)	0.0357 (3)
H2BA	1.1223	0.2127	0.9831	0.043*
H2BB	0.9966	0.1148	0.9803	0.043*
C3B	0.9547 (2)	0.25132 (15)	0.91350 (7)	0.0342 (3)
H3BA	0.8792	0.2016	0.8884	0.041*
H3BB	1.0079	0.2948	0.8874	0.041*
C4B	0.89090 (19)	0.35155 (16)	0.94935 (7)	0.0361 (3)
H4BA	0.8441	0.3063	0.9773	0.043*
H4BB	0.9677	0.4023	0.9731	0.043*
C5B	0.7856 (2)	0.44294 (16)	0.91214 (7)	0.0358 (3)
N1B	−0.04752 (17)	0.37734 (15)	0.17394 (7)	0.0453 (4)
H1BA	−0.1137	0.4333	0.1619	0.054*
N2B	0.26087 (18)	0.10594 (16)	0.23042 (7)	0.0494 (4)
H2BC	0.2914	0.0928	0.2684	0.059*
H2BD	0.2946	0.0613	0.2046	0.059*
C6B	0.0019 (2)	0.35827 (19)	0.23332 (8)	0.0440 (4)
H6BA	−0.0348	0.4067	0.2611	0.053*
C7B	0.1058 (2)	0.26829 (17)	0.25317 (7)	0.0402 (4)
H7BA	0.1392	0.2560	0.2943	0.048*
C8B	0.16224 (19)	0.19448 (17)	0.21178 (7)	0.0377 (3)
C9B	0.1092 (2)	0.21875 (18)	0.14972 (8)	0.0463 (4)
H9BA	0.1444	0.1734	0.1206	0.056*
C10B	0.0059 (2)	0.30944 (19)	0.13355 (8)	0.0494 (5)
H10B	−0.0291	0.3250	0.0927	0.059*

	U11	U22	U33	U12	U13	U23
O1A	0.0584 (8)	0.0587 (8)	0.0349 (6)	0.0303 (7)	0.0034 (6)	−0.0017 (6)
O2A	0.0626 (9)	0.0535 (7)	0.0270 (5)	0.0165 (7)	0.0085 (6)	−0.0009 (5)
O3A	0.0656 (9)	0.0597 (8)	0.0334 (6)	0.0320 (7)	0.0109 (6)	−0.0008 (6)
O4A	0.0568 (8)	0.0485 (7)	0.0289 (6)	0.0187 (6)	0.0043 (6)	−0.0008 (5)
C1A	0.0396 (9)	0.0387 (8)	0.0277 (7)	0.0068 (7)	0.0083 (6)	0.0003 (6)
C2A	0.0420 (9)	0.0428 (8)	0.0262 (7)	0.0128 (8)	0.0073 (6)	0.0014 (6)
C3A	0.0401 (8)	0.0367 (7)	0.0288 (7)	0.0081 (6)	0.0068 (7)	−0.0011 (6)
C4A	0.0397 (8)	0.0421 (8)	0.0274 (7)	0.0105 (8)	0.0056 (6)	−0.0012 (6)
C5A	0.0383 (8)	0.0351 (7)	0.0298 (7)	0.0065 (7)	0.0056 (6)	−0.0012 (6)
N1A	0.0506 (9)	0.0441 (8)	0.0422 (8)	0.0090 (7)	0.0148 (7)	−0.0026 (6)
N2A	0.0533 (10)	0.0551 (9)	0.0386 (8)	0.0173 (8)	0.0036 (7)	−0.0042 (7)
C6A	0.0620 (12)	0.0484 (10)	0.0347 (8)	0.0055 (10)	0.0071 (8)	−0.0039 (7)
C7A	0.0564 (12)	0.0457 (9)	0.0334 (8)	0.0097 (9)	0.0029 (8)	−0.0012 (7)
C8A	0.0392 (8)	0.0369 (8)	0.0362 (8)	0.0018 (7)	0.0048 (7)	−0.0005 (6)
C9A	0.0458 (10)	0.0465 (9)	0.0261 (7)	0.0040 (7)	0.0044 (7)	0.0019 (6)
C10A	0.0456 (10)	0.0477 (9)	0.0375 (8)	0.0034 (8)	0.0102 (7)	0.0027 (7)
O1B	0.0608 (8)	0.0608 (8)	0.0340 (6)	0.0342 (7)	0.0042 (6)	0.0021 (6)
O2B	0.0653 (9)	0.0533 (7)	0.0293 (6)	0.0242 (7)	0.0094 (6)	0.0018 (5)
O3B	0.0653 (9)	0.0577 (8)	0.0353 (6)	0.0334 (7)	0.0073 (6)	0.0009 (6)
O4B	0.0659 (9)	0.0579 (8)	0.0288 (6)	0.0227 (7)	−0.0008 (6)	−0.0005 (5)
C1B	0.0407 (9)	0.0373 (8)	0.0301 (7)	0.0084 (7)	0.0087 (7)	0.0018 (6)
C2B	0.0406 (9)	0.0380 (8)	0.0281 (7)	0.0122 (7)	0.0063 (6)	0.0011 (6)
C3B	0.0401 (8)	0.0344 (7)	0.0273 (7)	0.0066 (6)	0.0054 (7)	−0.0005 (6)
C4B	0.0398 (8)	0.0389 (7)	0.0279 (7)	0.0095 (7)	0.0032 (6)	−0.0035 (6)
C5B	0.0387 (9)	0.0343 (7)	0.0321 (7)	0.0076 (7)	0.0019 (6)	−0.0010 (6)
N1B	0.0458 (9)	0.0450 (8)	0.0424 (8)	0.0103 (7)	0.0030 (7)	0.0035 (6)
N2B	0.0553 (10)	0.0565 (9)	0.0368 (8)	0.0171 (8)	0.0105 (7)	0.0065 (7)
C6B	0.0468 (10)	0.0480 (9)	0.0368 (9)	0.0012 (9)	0.0078 (7)	−0.0046 (7)
C7B	0.0461 (10)	0.0455 (9)	0.0278 (7)	0.0047 (8)	0.0048 (7)	−0.0013 (6)
C8B	0.0406 (9)	0.0390 (8)	0.0342 (8)	0.0033 (7)	0.0095 (7)	0.0019 (6)
C9B	0.0577 (12)	0.0480 (9)	0.0330 (8)	0.0116 (9)	0.0093 (8)	−0.0003 (7)
C10B	0.0588 (12)	0.0554 (10)	0.0325 (9)	0.0105 (10)	0.0062 (8)	0.0045 (8)

O1A—C1A	1.299 (2)	O1B—C1B	1.2823 (19)
O1A—H1O1	0.8903	O2B—C1B	1.2303 (19)
O2A—C1A	1.2194 (18)	O3B—C5B	1.310 (2)
O3A—C5A	1.269 (2)	O3B—H1O3	0.9176
O4A—C5A	1.2423 (18)	O4B—C5B	1.2133 (19)
C1A—C2A	1.511 (2)	C1B—C2B	1.511 (2)
C2A—C3A	1.518 (2)	C2B—C3B	1.516 (2)
C2A—H2AA	0.9700	C2B—H2BA	0.9700
C2A—H2AB	0.9700	C2B—H2BB	0.9700
C3A—C4A	1.516 (2)	C3B—C4B	1.521 (2)
C3A—H3AA	0.9700	C3B—H3BA	0.9700
C3A—H3AB	0.9700	C3B—H3BB	0.9700
C4A—C5A	1.511 (2)	C4B—C5B	1.505 (2)
C4A—H4AA	0.9700	C4B—H4BA	0.9700
C4A—H4AB	0.9700	C4B—H4BB	0.9700
N1A—C10A	1.333 (2)	N1B—C10B	1.338 (2)
N1A—C6A	1.342 (2)	N1B—C6B	1.345 (2)
N1A—H1AA	0.8600	N1B—H1BA	0.8600
N2A—C8A	1.323 (2)	N2B—C8B	1.320 (2)
N2A—H2AC	0.8600	N2B—H2BC	0.8600
N2A—H2AD	0.8600	N2B—H2BD	0.8600
C6A—C7A	1.357 (3)	C6B—C7B	1.368 (3)
C6A—H6AA	0.9300	C6B—H6BA	0.9300
C7A—C8A	1.422 (2)	C7B—C8B	1.403 (2)
C7A—H7AA	0.9300	C7B—H7BA	0.9300
C8A—C9A	1.407 (2)	C8B—C9B	1.415 (2)
C9A—C10A	1.370 (3)	C9B—C10B	1.357 (3)
C9A—H9AA	0.9300	C9B—H9BA	0.9300
C10A—H10A	0.9300	C10B—H10B	0.9300
C1A—O1A—H1O1	120.0	C5B—O3B—H1O3	117.8
O2A—C1A—O1A	120.78 (15)	O2B—C1B—O1B	121.54 (15)
O2A—C1A—C2A	122.33 (15)	O2B—C1B—C2B	121.05 (14)
O1A—C1A—C2A	116.89 (13)	O1B—C1B—C2B	117.40 (13)
C1A—C2A—C3A	115.41 (12)	C1B—C2B—C3B	114.68 (13)
C1A—C2A—H2AA	108.4	C1B—C2B—H2BA	108.6
C3A—C2A—H2AA	108.4	C3B—C2B—H2BA	108.6
C1A—C2A—H2AB	108.4	C1B—C2B—H2BB	108.6
C3A—C2A—H2AB	108.4	C3B—C2B—H2BB	108.6
H2AA—C2A—H2AB	107.5	H2BA—C2B—H2BB	107.6
C4A—C3A—C2A	110.61 (12)	C2B—C3B—C4B	110.07 (12)
C4A—C3A—H3AA	109.5	C2B—C3B—H3BA	109.6
C2A—C3A—H3AA	109.5	C4B—C3B—H3BA	109.6
C4A—C3A—H3AB	109.5	C2B—C3B—H3BB	109.6
C2A—C3A—H3AB	109.5	C4B—C3B—H3BB	109.6
H3AA—C3A—H3AB	108.1	H3BA—C3B—H3BB	108.2
C5A—C4A—C3A	115.55 (13)	C5B—C4B—C3B	115.13 (13)
C5A—C4A—H4AA	108.4	C5B—C4B—H4BA	108.5
C3A—C4A—H4AA	108.4	C3B—C4B—H4BA	108.5
C5A—C4A—H4AB	108.4	C5B—C4B—H4BB	108.5
C3A—C4A—H4AB	108.4	C3B—C4B—H4BB	108.5
H4AA—C4A—H4AB	107.5	H4BA—C4B—H4BB	107.5
O4A—C5A—O3A	122.35 (15)	O4B—C5B—O3B	120.63 (15)
O4A—C5A—C4A	119.61 (14)	O4B—C5B—C4B	122.68 (15)
O3A—C5A—C4A	118.04 (13)	O3B—C5B—C4B	116.69 (13)
C10A—N1A—C6A	120.06 (16)	C10B—N1B—C6B	120.21 (16)
C10A—N1A—H1AA	120.0	C10B—N1B—H1BA	119.9
C6A—N1A—H1AA	120.0	C6B—N1B—H1BA	119.9
C8A—N2A—H2AC	120.0	C8B—N2B—H2BC	120.0
C8A—N2A—H2AD	120.0	C8B—N2B—H2BD	120.0
H2AC—N2A—H2AD	120.0	H2BC—N2B—H2BD	120.0
N1A—C6A—C7A	122.55 (17)	N1B—C6B—C7B	120.57 (17)
N1A—C6A—H6AA	118.7	N1B—C6B—H6BA	119.7
C7A—C6A—H6AA	118.7	C7B—C6B—H6BA	119.7
C6A—C7A—C8A	118.83 (17)	C6B—C7B—C8B	120.38 (16)
C6A—C7A—H7AA	120.6	C6B—C7B—H7BA	119.8
C8A—C7A—H7AA	120.6	C8B—C7B—H7BA	119.8
N2A—C8A—C9A	120.67 (16)	N2B—C8B—C7B	120.90 (15)
N2A—C8A—C7A	122.04 (16)	N2B—C8B—C9B	121.69 (16)
C9A—C8A—C7A	117.29 (16)	C7B—C8B—C9B	117.41 (16)
C10A—C9A—C8A	119.73 (16)	C10B—C9B—C8B	118.75 (17)
C10A—C9A—H9AA	120.1	C10B—C9B—H9BA	120.6
C8A—C9A—H9AA	120.1	C8B—C9B—H9BA	120.6
N1A—C10A—C9A	121.52 (17)	N1B—C10B—C9B	122.66 (17)
N1A—C10A—H10A	119.2	N1B—C10B—H10B	118.7
C9A—C10A—H10A	119.2	C9B—C10B—H10B	118.7
O2A—C1A—C2A—C3A	8.1 (3)	O2B—C1B—C2B—C3B	−4.8 (3)
O1A—C1A—C2A—C3A	−172.34 (16)	O1B—C1B—C2B—C3B	175.08 (17)
C1A—C2A—C3A—C4A	175.44 (15)	C1B—C2B—C3B—C4B	−175.99 (14)
C2A—C3A—C4A—C5A	174.42 (15)	C2B—C3B—C4B—C5B	−176.94 (15)
C3A—C4A—C5A—O4A	6.7 (3)	C3B—C4B—C5B—O4B	−5.5 (3)
C3A—C4A—C5A—O3A	−173.38 (17)	C3B—C4B—C5B—O3B	175.12 (16)
C10A—N1A—C6A—C7A	−0.6 (3)	C10B—N1B—C6B—C7B	−0.9 (3)
N1A—C6A—C7A—C8A	−0.3 (3)	N1B—C6B—C7B—C8B	0.0 (3)
C6A—C7A—C8A—N2A	−178.87 (18)	C6B—C7B—C8B—N2B	−178.91 (18)
C6A—C7A—C8A—C9A	1.1 (3)	C6B—C7B—C8B—C9B	1.0 (3)
N2A—C8A—C9A—C10A	178.99 (18)	N2B—C8B—C9B—C10B	178.79 (18)
C7A—C8A—C9A—C10A	−1.0 (3)	C7B—C8B—C9B—C10B	−1.1 (3)
C6A—N1A—C10A—C9A	0.8 (3)	C6B—N1B—C10B—C9B	0.8 (3)
C8A—C9A—C10A—N1A	0.1 (3)	C8B—C9B—C10B—N1B	0.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1O1···O1Bi	0.89	1.57	2.4591 (17)	172
N1A—H1AA···O1Bii	0.86	2.59	3.183 (2)	127
N1A—H1AA···O2Bii	0.86	1.87	2.729 (2)	177
N2A—H2AC···O2Aiii	0.86	2.18	2.9627 (19)	151
N2A—H2AD···O4B	0.86	2.10	2.948 (2)	170
O3B—H1O3···O3Aiv	0.92	1.56	2.4791 (17)	176
C10A—H10A···O4Bv	0.93	2.55	3.161 (2)	124
C7A—H7AA···O3B	0.93	2.47	3.370 (2)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1A—H1O1⋯O1Bi	0.89	1.57	2.4591 (17)	172
N1A—H1AA⋯O1Bii	0.86	2.59	3.183 (2)	127
N1A—H1AA⋯O2Bii	0.86	1.87	2.729 (2)	177
N2A—H2AC⋯O2Aiii	0.86	2.18	2.9627 (19)	151
N2A—H2AD⋯O4B	0.86	2.10	2.948 (2)	170
O3B—H1O3⋯O3Aiv	0.92	1.56	2.4791 (17)	176
C10A—H10A⋯O4Bv	0.93	2.55	3.161 (2)	124
C7A—H7AA⋯O3B	0.93	2.47	3.370 (2)	162

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