2-Amino-3-carb-oxy-pyridinium perchlorate.

The asymmetric unit includes two crystallographically independent equivalents of the title salt, C(6)H(7)N(2)O(2) (+)·ClO(4) (-). The cations and anions form separate layers alternating along the c axis, which are linked by N-H⋯O, O-H⋯O and C-H⋯O hydrogen bonds into a two-dimensional network parallel to (100). Further C-H⋯O contacts connect these layers, forming a three-dimensional network, in which R(4) (4)(20) rings and C(2) (2)(11) infinite chains can be identified.

Related literature

For structural studies of hybrid compounds of 2-amino­nicotinic acid, see: Akriche & Rzaigui (2007 ▶); Berrah et al. (2011a ▶,b ▶). For related perchlorate compounds, see: Toumi Akriche et al. (2010 ▶); Bendjeddou et al. (2003 ▶). For hydrogen-bond motifs, see: Etter et al. (1990 ▶); Grell et al. (1999 ▶).

Experimental

Crystal data

C6H7N2O2 +·ClO4 −

M = 238.59

Monoclinic,

a = 17.3573 (12) Å

b = 5.0800 (4) Å

c = 21.6293 (17) Å

β = 107.239 (2)°

V = 1821.5 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.43 mm−1

T = 150 K

0.48 × 0.17 × 0.08 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▶) T min = 0.847, T max = 0.966

13822 measured reflections

4142 independent reflections

3305 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.110

S = 1.11

4142 reflections

273 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.40 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812018922/ld2056sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812018922/ld2056Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812018922/ld2056Isup3.cml

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

C6H7N2O2+·ClO4−	F(000) = 976
Mr = 238.59	Dx = 1.74 Mg m−3
Monoclinic, P2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yc	Cell parameters from 3823 reflections
a = 17.3573 (12) Å	θ = 2.5–27.4°
b = 5.0800 (4) Å	µ = 0.43 mm−1
c = 21.6293 (17) Å	T = 150 K
β = 107.239 (2)°	Stick, colourless
V = 1821.5 (2) Å3	0.48 × 0.17 × 0.08 mm
Z = 8

Bruker APEXII diffractometer	3305 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
CCD rotation images, thin slices scans	θmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −22→12
Tmin = 0.847, Tmax = 0.966	k = −6→6
13822 measured reflections	l = −27→28
4142 independent reflections

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.0377P)2 + 1.7007P] where P = (Fo2 + 2Fc2)/3
4142 reflections	(Δ/σ)max < 0.001
273 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.40 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
Cl2	0.12456 (3)	−0.07231 (11)	−0.11690 (3)	0.01685 (14)
Cl1	0.37576 (3)	0.54151 (11)	0.35382 (3)	0.01875 (14)
O22	0.19785 (10)	−0.2141 (4)	−0.11310 (8)	0.0251 (4)
O1B	0.07544 (11)	0.1702 (4)	0.02704 (8)	0.0275 (4)
H1B	0.0786	0.0731	−0.0024	0.041*
O42	0.09107 (12)	−0.1755 (4)	−0.06809 (9)	0.0330 (5)
O21	0.42254 (13)	0.6540 (4)	0.31530 (9)	0.0369 (5)
O31	0.35147 (11)	0.2777 (3)	0.33137 (9)	0.0300 (4)
O41	0.30450 (11)	0.6993 (4)	0.34659 (8)	0.0264 (4)
O2B	0.18407 (11)	−0.0563 (4)	0.08267 (8)	0.0282 (4)
O32	0.14319 (11)	0.2034 (3)	−0.10376 (9)	0.0269 (4)
O2A	0.31277 (11)	0.5865 (4)	0.15454 (8)	0.0287 (4)
O11	0.42313 (11)	0.5324 (4)	0.42050 (8)	0.0269 (4)
O1A	0.42090 (11)	0.3499 (4)	0.20638 (8)	0.0323 (5)
H1A	0.4172	0.4352	0.2376	0.049*
O12	0.06824 (11)	−0.1019 (4)	−0.17999 (8)	0.0274 (4)
N2A	0.31083 (12)	0.1811 (4)	−0.01596 (9)	0.0189 (4)
H2A	0.2759	0.2114	−0.0528	0.023*
N2B	0.18027 (12)	0.3604 (4)	0.24939 (9)	0.0198 (4)
H2B	0.2137	0.3306	0.2869	0.024*
C3B	0.18684 (14)	0.2122 (4)	0.19911 (11)	0.0165 (5)
N1B	0.24371 (13)	0.0283 (4)	0.21094 (9)	0.0225 (5)
H11B	0.2751	0.0061	0.2496	0.027*
H12B	0.2492	−0.0685	0.1799	0.027*
C2B	0.13013 (14)	0.2659 (4)	0.13757 (11)	0.0156 (5)
C2A	0.36459 (14)	0.2707 (5)	0.09571 (11)	0.0166 (5)
N1A	0.24775 (12)	0.5022 (4)	0.02580 (9)	0.0204 (4)
H11A	0.2145	0.5237	−0.0122	0.025*
H12A	0.2432	0.5962	0.0576	0.025*
C3A	0.30586 (14)	0.3245 (4)	0.03538 (11)	0.0160 (5)
C5A	0.42317 (15)	−0.0621 (5)	0.04338 (12)	0.0239 (5)
H5A	0.4618	−0.1915	0.0457	0.029*
C6A	0.42192 (15)	0.0799 (5)	0.09851 (12)	0.0213 (5)
H6A	0.4605	0.0447	0.1378	0.026*
C4A	0.36681 (15)	−0.0065 (5)	−0.01335 (12)	0.0223 (5)
H4A	0.3666	−0.0978	−0.0507	0.027*
C6B	0.07394 (14)	0.4623 (5)	0.13287 (11)	0.0200 (5)
H6B	0.0373	0.4991	0.0927	0.024*
C1A	0.36249 (15)	0.4192 (5)	0.15434 (11)	0.0199 (5)
C1B	0.13334 (15)	0.1106 (5)	0.08066 (11)	0.0183 (5)
C4B	0.12476 (15)	0.5518 (5)	0.24461 (12)	0.0229 (5)
H4B	0.1238	0.6456	0.2813	0.027*
C5B	0.07058 (15)	0.6081 (5)	0.18698 (12)	0.0222 (5)
H5B	0.0322	0.7396	0.1833	0.027*

	U11	U22	U33	U12	U13	U23
Cl2	0.0180 (3)	0.0159 (3)	0.0166 (3)	0.0000 (2)	0.0052 (2)	−0.0011 (2)
Cl1	0.0213 (3)	0.0159 (3)	0.0199 (3)	−0.0054 (2)	0.0074 (2)	−0.0038 (2)
O22	0.0216 (9)	0.0260 (10)	0.0251 (9)	0.0067 (7)	0.0028 (7)	−0.0018 (7)
O1B	0.0229 (10)	0.0384 (11)	0.0194 (9)	0.0070 (8)	0.0036 (7)	−0.0085 (8)
O42	0.0463 (12)	0.0321 (11)	0.0289 (10)	−0.0153 (9)	0.0242 (9)	−0.0079 (8)
O21	0.0472 (13)	0.0380 (12)	0.0356 (11)	−0.0184 (10)	0.0275 (10)	−0.0084 (9)
O31	0.0327 (11)	0.0164 (9)	0.0365 (11)	−0.0060 (8)	0.0034 (9)	−0.0079 (8)
O41	0.0268 (10)	0.0233 (9)	0.0271 (9)	0.0037 (8)	0.0050 (8)	−0.0032 (8)
O2B	0.0348 (11)	0.0259 (10)	0.0228 (9)	0.0121 (8)	0.0067 (8)	−0.0040 (8)
O32	0.0322 (11)	0.0143 (9)	0.0295 (10)	0.0002 (7)	0.0019 (8)	−0.0008 (7)
O2A	0.0334 (11)	0.0286 (10)	0.0225 (9)	0.0122 (8)	0.0058 (8)	−0.0031 (8)
O11	0.0237 (10)	0.0305 (10)	0.0227 (9)	−0.0036 (8)	0.0013 (7)	−0.0032 (8)
O1A	0.0249 (10)	0.0511 (13)	0.0176 (9)	0.0117 (9)	0.0010 (8)	−0.0044 (9)
O12	0.0232 (9)	0.0331 (11)	0.0214 (9)	0.0054 (8)	−0.0005 (7)	−0.0064 (8)
N2A	0.0215 (11)	0.0188 (10)	0.0156 (9)	0.0020 (8)	0.0044 (8)	0.0008 (8)
N2B	0.0230 (11)	0.0192 (10)	0.0165 (9)	−0.0029 (8)	0.0047 (8)	−0.0026 (8)
C3B	0.0185 (12)	0.0137 (11)	0.0182 (11)	−0.0045 (9)	0.0071 (9)	−0.0022 (9)
N1B	0.0279 (12)	0.0187 (10)	0.0182 (10)	0.0048 (9)	0.0024 (8)	−0.0005 (8)
C2B	0.0167 (12)	0.0127 (10)	0.0186 (11)	−0.0040 (9)	0.0071 (9)	−0.0013 (9)
C2A	0.0149 (12)	0.0162 (11)	0.0190 (11)	−0.0007 (9)	0.0055 (9)	0.0020 (9)
N1A	0.0227 (11)	0.0177 (10)	0.0178 (9)	0.0073 (8)	0.0012 (8)	−0.0002 (8)
C3A	0.0177 (12)	0.0125 (10)	0.0186 (11)	−0.0025 (9)	0.0067 (9)	0.0012 (9)
C5A	0.0213 (13)	0.0204 (12)	0.0326 (13)	0.0071 (10)	0.0120 (11)	0.0006 (11)
C6A	0.0187 (12)	0.0225 (12)	0.0222 (12)	0.0015 (10)	0.0050 (10)	0.0044 (10)
C4A	0.0267 (13)	0.0174 (12)	0.0260 (12)	0.0003 (10)	0.0127 (10)	−0.0035 (10)
C6B	0.0179 (12)	0.0187 (12)	0.0230 (11)	−0.0025 (10)	0.0053 (9)	−0.0005 (10)
C1A	0.0219 (13)	0.0201 (12)	0.0176 (11)	−0.0015 (10)	0.0056 (10)	0.0014 (9)
C1B	0.0201 (12)	0.0169 (12)	0.0183 (11)	−0.0018 (10)	0.0062 (9)	−0.0009 (9)
C4B	0.0279 (14)	0.0193 (12)	0.0251 (12)	−0.0043 (11)	0.0135 (10)	−0.0075 (10)
C5B	0.0213 (13)	0.0174 (12)	0.0302 (13)	0.0012 (10)	0.0112 (11)	−0.0047 (10)

Cl2—O12	1.4316 (17)	C3B—C2B	1.428 (3)
Cl2—O22	1.4427 (18)	N1B—H11B	0.86
Cl2—O42	1.4463 (18)	N1B—H12B	0.86
Cl2—O32	1.4466 (18)	C2B—C6B	1.378 (3)
Cl1—O11	1.4336 (17)	C2B—C1B	1.477 (3)
Cl1—O21	1.4427 (19)	C2A—C6A	1.378 (3)
Cl1—O41	1.4430 (18)	C2A—C3A	1.424 (3)
Cl1—O31	1.4451 (18)	C2A—C1A	1.485 (3)
O1B—C1B	1.325 (3)	N1A—C3A	1.324 (3)
O1B—H1B	0.82	N1A—H11A	0.86
O2B—C1B	1.214 (3)	N1A—H12A	0.86
O2A—C1A	1.212 (3)	C5A—C4A	1.353 (3)
O1A—C1A	1.320 (3)	C5A—C6A	1.399 (3)
O1A—H1A	0.82	C5A—H5A	0.93
N2A—C4A	1.350 (3)	C6A—H6A	0.93
N2A—C3A	1.352 (3)	C4A—H4A	0.93
N2A—H2A	0.86	C6B—C5B	1.401 (3)
N2B—C4B	1.351 (3)	C6B—H6B	0.93
N2B—C3B	1.355 (3)	C4B—C5B	1.351 (3)
N2B—H2B	0.86	C4B—H4B	0.93
C3B—N1B	1.328 (3)	C5B—H5B	0.93
O12—Cl2—O22	110.08 (10)	C3A—C2A—C1A	119.5 (2)
O12—Cl2—O42	110.43 (12)	C3A—N1A—H11A	120
O22—Cl2—O42	108.41 (12)	C3A—N1A—H12A	120
O12—Cl2—O32	109.81 (11)	H11A—N1A—H12A	120
O22—Cl2—O32	109.27 (11)	N1A—C3A—N2A	118.0 (2)
O42—Cl2—O32	108.81 (11)	N1A—C3A—C2A	125.4 (2)
O11—Cl1—O21	109.92 (11)	N2A—C3A—C2A	116.5 (2)
O11—Cl1—O41	110.16 (11)	C4A—C5A—C6A	118.4 (2)
O21—Cl1—O41	109.17 (12)	C4A—C5A—H5A	120.8
O11—Cl1—O31	109.34 (11)	C6A—C5A—H5A	120.8
O21—Cl1—O31	109.36 (12)	C2A—C6A—C5A	121.2 (2)
O41—Cl1—O31	108.87 (11)	C2A—C6A—H6A	119.4
C1B—O1B—H1B	109.5	C5A—C6A—H6A	119.4
C1A—O1A—H1A	109.5	N2A—C4A—C5A	120.2 (2)
C4A—N2A—C3A	124.5 (2)	N2A—C4A—H4A	119.9
C4A—N2A—H2A	117.8	C5A—C4A—H4A	119.9
C3A—N2A—H2A	117.8	C2B—C6B—C5B	121.7 (2)
C4B—N2B—C3B	124.5 (2)	C2B—C6B—H6B	119.2
C4B—N2B—H2B	117.8	C5B—C6B—H6B	119.2
C3B—N2B—H2B	117.8	O2A—C1A—O1A	123.5 (2)
N1B—C3B—N2B	118.1 (2)	O2A—C1A—C2A	123.8 (2)
N1B—C3B—C2B	125.6 (2)	O1A—C1A—C2A	112.7 (2)
N2B—C3B—C2B	116.3 (2)	O2B—C1B—O1B	123.0 (2)
C3B—N1B—H11B	120	O2B—C1B—C2B	123.3 (2)
C3B—N1B—H12B	120	O1B—C1B—C2B	113.6 (2)
H11B—N1B—H12B	120	C5B—C4B—N2B	120.6 (2)
C6B—C2B—C3B	119.0 (2)	C5B—C4B—H4B	119.7
C6B—C2B—C1B	121.7 (2)	N2B—C4B—H4B	119.7
C3B—C2B—C1B	119.3 (2)	C4B—C5B—C6B	118.0 (2)
C6A—C2A—C3A	119.1 (2)	C4B—C5B—H5B	121
C6A—C2A—C1A	121.3 (2)	C6B—C5B—H5B	121
C4B—N2B—C3B—N1B	−179.2 (2)	C3A—N2A—C4A—C5A	−0.1 (4)
C4B—N2B—C3B—C2B	−0.3 (3)	C6A—C5A—C4A—N2A	−0.3 (4)
N1B—C3B—C2B—C6B	179.4 (2)	C3B—C2B—C6B—C5B	−0.7 (4)
N2B—C3B—C2B—C6B	0.7 (3)	C1B—C2B—C6B—C5B	179.5 (2)
N1B—C3B—C2B—C1B	−0.8 (4)	C6A—C2A—C1A—O2A	−179.1 (2)
N2B—C3B—C2B—C1B	−179.6 (2)	C3A—C2A—C1A—O2A	0.4 (4)
C4A—N2A—C3A—N1A	−180.0 (2)	C6A—C2A—C1A—O1A	1.1 (3)
C4A—N2A—C3A—C2A	0.2 (3)	C3A—C2A—C1A—O1A	−179.4 (2)
C6A—C2A—C3A—N1A	−179.8 (2)	C6B—C2B—C1B—O2B	176.9 (2)
C1A—C2A—C3A—N1A	0.7 (4)	C3B—C2B—C1B—O2B	−2.8 (4)
C6A—C2A—C3A—N2A	0.0 (3)	C6B—C2B—C1B—O1B	−3.2 (3)
C1A—C2A—C3A—N2A	−179.6 (2)	C3B—C2B—C1B—O1B	177.1 (2)
C3A—C2A—C6A—C5A	−0.3 (4)	C3B—N2B—C4B—C5B	0.0 (4)
C1A—C2A—C6A—C5A	179.2 (2)	N2B—C4B—C5B—C6B	0.0 (4)
C4A—C5A—C6A—C2A	0.5 (4)	C2B—C6B—C5B—C4B	0.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···O21	0.82	1.99	2.810 (3)	173
O1B—H1B···O42	0.82	1.96	2.779 (3)	176
N2A—H2A···O32	0.86	2.24	2.968 (3)	142
N2A—H2A···O41i	0.86	2.41	3.004 (3)	126
N2B—H2B···O31	0.86	2.31	3.005 (3)	138
N2B—H2B···O41	0.86	2.54	3.057 (3)	120
N2B—H2B···O22ii	0.86	2.34	2.992 (3)	133
N1A—H11A···O22iii	0.86	2.50	3.211 (3)	141
N1A—H11A···O32	0.86	2.58	3.231 (3)	133
N1B—H11B···O31	0.86	2.32	3.000 (3)	136
N1B—H11B···O41iv	0.86	2.54	3.268 (3)	143
N1A—H12A···O2A	0.86	2.09	2.711 (3)	129
N1A—H12A···O2Biii	0.86	2.19	2.928 (3)	144
N1B—H12B···O2Aiv	0.86	2.22	2.971 (3)	145
N1B—H12B···O2B	0.86	2.07	2.693 (3)	128
C4A—H4A···O11v	0.93	2.57	3.312 (3)	137
C4B—H4B···O32vi	0.93	2.53	3.433 (3)	165
C5A—H5A···O11vii	0.93	2.37	3.277 (3)	164
C5B—H5B···O12viii	0.93	2.52	3.450 (3)	177
C6A—H6A···O1A	0.93	2.38	2.711 (3)	100
C6B—H6B···O1B	0.93	2.41	2.735 (3)	100

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1A—H1A⋯O21	0.82	1.99	2.810 (3)	173
O1B—H1B⋯O42	0.82	1.96	2.779 (3)	176
N2A—H2A⋯O32	0.86	2.24	2.968 (3)	142
N2B—H2B⋯O31	0.86	2.31	3.005 (3)	138
N2B—H2B⋯O22i	0.86	2.34	2.992 (3)	133
N1A—H11A⋯O22ii	0.86	2.50	3.211 (3)	141
N1A—H11A⋯O32	0.86	2.58	3.231 (3)	133
N1B—H11B⋯O31	0.86	2.32	3.000 (3)	136
N1B—H11B⋯O41iii	0.86	2.54	3.268 (3)	143
N1A—H12A⋯O2Bii	0.86	2.19	2.928 (3)	144
N1B—H12B⋯O2Aiii	0.86	2.22	2.971 (3)	145
C4A—H4A⋯O11iv	0.93	2.57	3.312 (3)	137
C4B—H4B⋯O32v	0.93	2.53	3.433 (3)	165
C5A—H5A⋯O11vi	0.93	2.37	3.277 (3)	164
C5B—H5B⋯O12vii	0.93	2.52	3.450 (3)	177

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