2-Amino-3-carb-oxy-pyridinium chloride hemihydrate.

The asymmetric unit of the title compound, C(6)H(7)N(2)O(2) (+)·Cl(-)·0.5H(2)O, consists of two protonated 2-amino-3-carb-oxy-pyridine cations, two chloride anions and one mol-ecule of water. The crystal packing can be described as alternating layers of cations and anions parallel to (110), which are linked together by O(w)-H⋯Cl inter-actions. In the crystal, four types of classical hydrogen bonds are observed, viz. cation-anion (O-H⋯Cl and N-H⋯Cl), cation-cation (N-H⋯O), cation-water (N-H⋯O(w)) and water-anion (O(w)-H⋯Cl), resulting in the formation of an infinite three-dimensional network.

Related literature

For applications of hybrid organic–inorganic compounds, see: Bouacida (2008 ▶); Kickelbick (2007 ▶); Mitzi et al. (1998 ▶); Asaji et al. (2007 ▶); Lynch & Jones (2004 ▶). For related structures, see: Beatty (2003 ▶); Sengupta et al. (2001 ▶); Berrah et al. (2011a ▶,b ▶,c ▶); Akriche & Rzaigui (2007 ▶).

Experimental

Crystal data

C6H7N2O2 +·Cl−·0.5H2O

M = 183.60

Triclinic,

a = 7.8949 (4) Å

b = 9.1639 (5) Å

c = 11.0285 (6) Å

α = 81.392 (4)°

β = 81.276 (3)°

γ = 81.682 (4)°

V = 773.68 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.45 mm−1

T = 180 K

0.1 × 0.08 × 0.06 mm

Data collection

Agilent Xcalibur Sapphire1 long-nozzle diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.831, T max = 1

14449 measured reflections

3600 independent reflections

2857 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.08

S = 1.01

3600 reflections

214 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.28 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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 DIAMOND (Brandenburg & Berndt, 2001 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812017230/bq2352sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812017230/bq2352Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812017230/bq2352Isup3.cml

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

C6H7N2O2+·Cl−·0.5H2O	Z = 4
Mr = 183.60	F(000) = 380
Triclinic, P1	Dx = 1.576 Mg m−3
a = 7.8949 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.1639 (5) Å	Cell parameters from 8921 reflections
c = 11.0285 (6) Å	θ = 3.0–28.3°
α = 81.392 (4)°	µ = 0.45 mm−1
β = 81.276 (3)°	T = 180 K
γ = 81.682 (4)°	Box, colourless
V = 773.68 (7) Å3	0.1 × 0.08 × 0.06 mm

Agilent Xcalibur Sapphire1 long-nozzle diffractometer	3600 independent reflections
Radiation source: fine-focus sealed tube	2857 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
Detector resolution: 8.2632 pixels mm-1	θmax = 28.4°, θmin = 3.0°
ω scans	h = −10→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −12→12
Tmin = 0.831, Tmax = 1	l = −13→14
14449 measured 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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.08	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0442P)2 + 0.1332P] where P = (Fo2 + 2Fc2)/3
3600 reflections	(Δ/σ)max = 0.006
214 parameters	Δρmax = 0.26 e Å−3
3 restraints	Δρmin = −0.28 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
N3A	−0.02482 (16)	0.24894 (14)	0.18532 (11)	0.0277 (3)
H3A1	−0.0772	0.2962	0.2448	0.033*
H3A2	−0.0497	0.2761	0.1114	0.033*
N3B	0.13489 (17)	0.59931 (14)	0.23112 (12)	0.0291 (3)
H3B1	0.0857	0.6432	0.2933	0.035*
H3B2	0.1053	0.6298	0.1588	0.035*
O1W	0.33167 (15)	0.38876 (12)	0.72134 (10)	0.0306 (2)
H1W	0.287 (2)	0.3146 (14)	0.7070 (17)	0.046*
H2W	0.280 (2)	0.4650 (14)	0.6834 (16)	0.046*
Cl1	0.19706 (5)	0.11808 (4)	0.64870 (3)	0.03012 (11)
Cl2	0.14081 (5)	0.65043 (4)	0.55111 (3)	0.03071 (11)
O1A	0.05136 (14)	0.18895 (12)	−0.04721 (9)	0.0301 (2)
O2A	0.26652 (14)	0.01182 (12)	−0.09112 (9)	0.0287 (2)
H2A	0.2445	0.0392	−0.1619	0.043*
O1B	0.20803 (14)	0.54951 (12)	−0.00916 (10)	0.0333 (3)
N4A	0.12830 (15)	0.09603 (13)	0.32534 (10)	0.0220 (2)
H4A	0.074	0.1486	0.3809	0.026*
N4B	0.29795 (16)	0.44117 (14)	0.36162 (11)	0.0259 (3)
H4B	0.2425	0.488	0.4204	0.031*
C2B	0.34601 (17)	0.40270 (14)	0.15203 (12)	0.0193 (3)
C2A	0.19059 (17)	0.05053 (15)	0.11658 (12)	0.0196 (3)
C3A	0.09315 (17)	0.13510 (15)	0.20751 (12)	0.0201 (3)
C5A	0.24283 (19)	−0.01981 (16)	0.36061 (13)	0.0256 (3)
H5A	0.2593	−0.0421	0.4434	0.031*
C7A	0.30817 (19)	−0.06680 (16)	0.15319 (13)	0.0238 (3)
H7A	0.372	−0.1227	0.0942	0.029*
C1A	0.16107 (18)	0.09171 (15)	−0.01399 (12)	0.0210 (3)
O2B	0.38993 (13)	0.34859 (11)	−0.05118 (9)	0.0272 (2)
H2B	0.3638	0.3747	−0.1211	0.041*
C1B	0.30608 (17)	0.44226 (15)	0.02359 (12)	0.0209 (3)
C7B	0.47068 (18)	0.28766 (16)	0.18251 (13)	0.0227 (3)
H7B	0.5304	0.2339	0.1208	0.027*
C3B	0.25557 (18)	0.48538 (15)	0.24663 (13)	0.0218 (3)
C5B	0.4206 (2)	0.32921 (17)	0.39066 (14)	0.0279 (3)
H5B	0.4441	0.3064	0.4719	0.033*
C6B	0.51055 (19)	0.24892 (17)	0.30269 (13)	0.0264 (3)
H6B	0.5956	0.171	0.322	0.032*
C6A	0.3345 (2)	−0.10448 (17)	0.27672 (14)	0.0281 (3)
H6A	0.413	−0.1856	0.3008	0.034*

	U11	U22	U33	U12	U13	U23
N3A	0.0289 (7)	0.0298 (7)	0.0217 (6)	0.0094 (6)	−0.0026 (5)	−0.0084 (5)
N3B	0.0302 (7)	0.0268 (6)	0.0280 (7)	0.0051 (6)	−0.0008 (5)	−0.0080 (5)
O1W	0.0410 (7)	0.0254 (6)	0.0259 (5)	0.0005 (5)	−0.0104 (5)	−0.0036 (4)
Cl1	0.0377 (2)	0.0322 (2)	0.02155 (18)	−0.00542 (16)	−0.00607 (15)	−0.00379 (14)
Cl2	0.0382 (2)	0.0302 (2)	0.02172 (18)	0.00677 (16)	−0.00392 (15)	−0.00771 (14)
O1A	0.0310 (6)	0.0335 (6)	0.0227 (5)	0.0100 (5)	−0.0058 (4)	−0.0049 (4)
O2A	0.0349 (6)	0.0301 (6)	0.0179 (5)	0.0084 (5)	−0.0028 (4)	−0.0059 (4)
O1B	0.0351 (6)	0.0326 (6)	0.0278 (6)	0.0113 (5)	−0.0065 (5)	−0.0024 (4)
N4A	0.0249 (6)	0.0228 (6)	0.0185 (5)	−0.0021 (5)	−0.0001 (5)	−0.0062 (4)
N4B	0.0261 (6)	0.0306 (7)	0.0208 (6)	−0.0008 (5)	0.0008 (5)	−0.0093 (5)
C2B	0.0190 (6)	0.0178 (6)	0.0209 (6)	−0.0034 (5)	−0.0004 (5)	−0.0032 (5)
C2A	0.0190 (7)	0.0188 (6)	0.0209 (7)	−0.0021 (5)	−0.0015 (5)	−0.0042 (5)
C3A	0.0193 (7)	0.0216 (7)	0.0197 (6)	−0.0041 (5)	−0.0017 (5)	−0.0033 (5)
C5A	0.0304 (8)	0.0265 (7)	0.0202 (7)	−0.0028 (6)	−0.0061 (6)	−0.0014 (6)
C7A	0.0250 (7)	0.0223 (7)	0.0232 (7)	0.0005 (6)	−0.0013 (6)	−0.0055 (5)
C1A	0.0211 (7)	0.0212 (7)	0.0204 (7)	−0.0028 (6)	−0.0003 (5)	−0.0045 (5)
O2B	0.0330 (6)	0.0277 (5)	0.0197 (5)	0.0050 (5)	−0.0058 (4)	−0.0058 (4)
C1B	0.0191 (7)	0.0204 (7)	0.0225 (7)	−0.0017 (6)	−0.0007 (5)	−0.0039 (5)
C7B	0.0224 (7)	0.0227 (7)	0.0232 (7)	−0.0025 (6)	−0.0009 (6)	−0.0058 (5)
C3B	0.0201 (7)	0.0217 (7)	0.0239 (7)	−0.0049 (6)	−0.0005 (5)	−0.0043 (5)
C5B	0.0284 (8)	0.0344 (8)	0.0210 (7)	−0.0043 (7)	−0.0050 (6)	−0.0024 (6)
C6B	0.0247 (7)	0.0269 (7)	0.0264 (7)	0.0007 (6)	−0.0059 (6)	−0.0013 (6)
C6A	0.0300 (8)	0.0249 (7)	0.0273 (7)	0.0049 (6)	−0.0070 (6)	−0.0018 (6)

N3A—C3A	1.3143 (18)	C2B—C7B	1.3738 (19)
N3A—H3A1	0.86	C2B—C3B	1.4236 (19)
N3A—H3A2	0.86	C2B—C1B	1.4785 (18)
N3B—C3B	1.3172 (18)	C2A—C7A	1.3695 (19)
N3B—H3B1	0.86	C2A—C3A	1.4227 (19)
N3B—H3B2	0.86	C2A—C1A	1.4778 (18)
O1W—H1W	0.854 (9)	C5A—C6A	1.353 (2)
O1W—H2W	0.843 (9)	C5A—H5A	0.93
O1A—C1A	1.2058 (17)	C7A—C6A	1.394 (2)
O2A—C1A	1.3221 (16)	C7A—H7A	0.93
O2A—H2A	0.82	O2B—C1B	1.3179 (16)
O1B—C1B	1.2058 (17)	O2B—H2B	0.82
N4A—C5A	1.3420 (18)	C7B—C6B	1.3911 (19)
N4A—C3A	1.3548 (17)	C7B—H7B	0.93
N4A—H4A	0.86	C5B—C6B	1.357 (2)
N4B—C5B	1.342 (2)	C5B—H5B	0.93
N4B—C3B	1.3491 (18)	C6B—H6B	0.93
N4B—H4B	0.86	C6A—H6A	0.93
C3A—N3A—H3A1	120	C2A—C7A—C6A	121.60 (13)
C3A—N3A—H3A2	120	C2A—C7A—H7A	119.2
H3A1—N3A—H3A2	120	C6A—C7A—H7A	119.2
C3B—N3B—H3B1	120	O1A—C1A—O2A	123.10 (12)
C3B—N3B—H3B2	120	O1A—C1A—C2A	123.28 (12)
H3B1—N3B—H3B2	120	O2A—C1A—C2A	113.62 (12)
H1W—O1W—H2W	106.3 (15)	C1B—O2B—H2B	109.5
C1A—O2A—H2A	109.5	O1B—C1B—O2B	123.72 (13)
C5A—N4A—C3A	123.91 (12)	O1B—C1B—C2B	123.43 (12)
C5A—N4A—H4A	118	O2B—C1B—C2B	112.84 (12)
C3A—N4A—H4A	118	C2B—C7B—C6B	122.19 (13)
C5B—N4B—C3B	124.58 (13)	C2B—C7B—H7B	118.9
C5B—N4B—H4B	117.7	C6B—C7B—H7B	118.9
C3B—N4B—H4B	117.7	N3B—C3B—N4B	118.05 (13)
C7B—C2B—C3B	118.77 (12)	N3B—C3B—C2B	125.61 (13)
C7B—C2B—C1B	121.29 (12)	N4B—C3B—C2B	116.33 (13)
C3B—C2B—C1B	119.94 (12)	N4B—C5B—C6B	120.70 (13)
C7A—C2A—C3A	118.82 (12)	N4B—C5B—H5B	119.7
C7A—C2A—C1A	122.21 (12)	C6B—C5B—H5B	119.7
C3A—C2A—C1A	118.96 (12)	C5B—C6B—C7B	117.41 (14)
N3A—C3A—N4A	118.07 (12)	C5B—C6B—H6B	121.3
N3A—C3A—C2A	125.06 (12)	C7B—C6B—H6B	121.3
N4A—C3A—C2A	116.85 (12)	C5A—C6A—C7A	118.20 (14)
N4A—C5A—C6A	120.56 (13)	C5A—C6A—H6A	120.9
N4A—C5A—H5A	119.7	C7A—C6A—H6A	120.9
C6A—C5A—H5A	119.7
C5A—N4A—C3A—N3A	178.44 (13)	C7B—C2B—C1B—O2B	5.75 (18)
C5A—N4A—C3A—C2A	−2.8 (2)	C3B—C2B—C1B—O2B	−174.82 (12)
C7A—C2A—C3A—N3A	−179.18 (14)	C3B—C2B—C7B—C6B	0.4 (2)
C1A—C2A—C3A—N3A	0.5 (2)	C1B—C2B—C7B—C6B	179.82 (13)
C7A—C2A—C3A—N4A	2.20 (19)	C5B—N4B—C3B—N3B	−178.55 (13)
C1A—C2A—C3A—N4A	−178.08 (12)	C5B—N4B—C3B—C2B	1.8 (2)
C3A—N4A—C5A—C6A	1.4 (2)	C7B—C2B—C3B—N3B	179.06 (13)
C3A—C2A—C7A—C6A	−0.2 (2)	C1B—C2B—C3B—N3B	−0.4 (2)
C1A—C2A—C7A—C6A	−179.93 (14)	C7B—C2B—C3B—N4B	−1.36 (19)
C7A—C2A—C1A—O1A	175.54 (13)	C1B—C2B—C3B—N4B	179.19 (12)
C3A—C2A—C1A—O1A	−4.2 (2)	C3B—N4B—C5B—C6B	−1.3 (2)
C7A—C2A—C1A—O2A	−4.50 (19)	N4B—C5B—C6B—C7B	0.1 (2)
C3A—C2A—C1A—O2A	175.79 (12)	C2B—C7B—C6B—C5B	0.3 (2)
C7B—C2B—C1B—O1B	−173.77 (14)	N4A—C5A—C6A—C7A	0.8 (2)
C3B—C2B—C1B—O1B	5.7 (2)	C2A—C7A—C6A—C5A	−1.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···Cl1	0.85 (1)	2.24 (1)	3.0887 (12)	173 (2)
O1W—H2W···Cl2	0.84 (2)	2.33 (2)	3.1639 (12)	170 (2)
O2A—H2A···Cl1i	0.82	2.18	2.9948 (11)	177
O2B—H2B···O1Wi	0.82	1.78	2.5818 (15)	166
N3B—H3B2···O1B	0.86	2.10	2.7176 (17)	128
N3B—H3B2···O1Aii	0.86	2.25	2.9903 (17)	144
N3A—H3A2···O1A	0.86	2.04	2.6644 (16)	129
N3A—H3A2···O1Bii	0.86	2.17	2.8781 (17)	140
N3A—H3A1···Cl2iii	0.86	2.34	3.1447 (13)	156
N4A—H4A···Cl2iii	0.86	2.44	3.2265 (12)	152
N4B—H4B···Cl2	0.86	2.21	3.0510 (13)	166
C5A—H5A···Cl1	0.93	2.82	3.5417 (15)	135
C6A—H6A···O1Wiv	0.93	2.55	3.427 (2)	158
C7A—H7A···O2A	0.93	2.42	2.7397 (17)	100
C7B—H7B···O2B	0.93	2.37	2.7065 (17)	101

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯Cl1	0.85 (1)	2.24 (1)	3.0887 (12)	173 (2)
O1W—H2W⋯Cl2	0.84 (2)	2.33 (2)	3.1639 (12)	170 (2)
O2A—H2A⋯Cl1i	0.82	2.18	2.9948 (11)	177
O2B—H2B⋯O1Wi	0.82	1.78	2.5818 (15)	166
N3B—H3B2⋯O1B	0.86	2.10	2.7176 (17)	128
N3B—H3B2⋯O1Aii	0.86	2.25	2.9903 (17)	144
N3A—H3A2⋯O1A	0.86	2.04	2.6644 (16)	129
N3A—H3A2⋯O1Bii	0.86	2.17	2.8781 (17)	140
N3A—H3A1⋯Cl2iii	0.86	2.34	3.1447 (13)	156
N4A—H4A⋯Cl2iii	0.86	2.44	3.2265 (12)	152
N4B—H4B⋯Cl2	0.86	2.21	3.0510 (13)	166

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