2-Amino-5-chloro-pyridinium 6-oxo-1,6-dihydro-pyridine-2-carboxyl-ate 0.85-hydrate.

In the title salt, C(5)H(6)ClN(2) (+)·C(6)H(4)NO(3) (-)·0.85H(2)O, the pyridin-ium ring is planar, with a maximum deviation of 0.010 (2) Å. In the crystal structure, the cations, anions and water mol-ecules are linked via N-H⋯O, O-H⋯O and C-H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

For applications of inter­molecular inter­actions, see: Braga et al. (2002 ▶); Lam & Mak (2000 ▶). For related structures, see: Hemamalini & Fun (2010a ▶,b ▶,c ▶,d ▶,e ▶,f ▶); Sawada & Ohashi (1998 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C5H6ClN2 +·C6H4NO3 −·0.85H2O

M = 282.98

Orthorhombic,

a = 3.8096 (1) Å

b = 15.6046 (3) Å

c = 20.9370 (3) Å

V = 1244.65 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.32 mm−1

T = 296 K

0.52 × 0.22 × 0.11 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.851, T max = 0.966

15196 measured reflections

3632 independent reflections

3129 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.113

S = 1.10

3632 reflections

215 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.17 e Å−3

Absolute structure: Flack (1983 ▶), with 1458 Fridel pairs

Flack parameter: −0.04 (6)

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/S1600536810032307/ci5153sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810032307/ci5153Isup2.hkl

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

C5H6ClN2+·C6H4NO3−·0.85H2O	F(000) = 586
Mr = 282.98	Dx = 1.510 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 6806 reflections
a = 3.8096 (1) Å	θ = 2.3–29.0°
b = 15.6046 (3) Å	µ = 0.32 mm−1
c = 20.9370 (3) Å	T = 296 K
V = 1244.65 (4) Å3	Needle, green
Z = 4	0.52 × 0.22 × 0.11 mm

Bruker SMART APEXII CCD area-detector diffractometer	3632 independent reflections
Radiation source: fine-focus sealed tube	3129 reflections with I > 2σ(I)
graphite	Rint = 0.026
φ and ω scans	θmax = 30.1°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −4→5
Tmin = 0.851, Tmax = 0.966	k = −21→21
15196 measured reflections	l = −29→29

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)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.113	w = 1/[σ2(Fo2) + (0.0653P)2 + 0.0443P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max = 0.001
3632 reflections	Δρmax = 0.20 e Å−3
215 parameters	Δρmin = −0.17 e Å−3
0 restraints	Absolute structure: Flack (1983), with 1458 Fridel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.04 (6)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	Occ. (<1)
Cl1	0.29968 (15)	0.97559 (3)	1.16268 (2)	0.04826 (15)
N1	0.0504 (4)	0.98883 (9)	0.97983 (7)	0.0358 (3)
N2	0.1288 (6)	0.90253 (11)	0.89193 (7)	0.0473 (4)
C1	0.0873 (5)	1.00748 (10)	1.04320 (8)	0.0365 (4)
C2	0.1708 (5)	0.91546 (9)	0.95385 (8)	0.0339 (3)
C3	0.3321 (6)	0.85531 (10)	0.99503 (8)	0.0378 (4)
C4	0.3690 (5)	0.87223 (11)	1.05852 (9)	0.0389 (4)
C5	0.2467 (5)	0.95094 (10)	1.08254 (7)	0.0361 (4)
O1	0.8680 (5)	0.75705 (8)	0.15429 (5)	0.0483 (4)
O2	0.6524 (5)	0.96179 (8)	0.31378 (6)	0.0527 (4)
O3	0.8337 (5)	0.90935 (8)	0.40756 (6)	0.0516 (4)
N3	0.8628 (4)	0.82238 (9)	0.25126 (6)	0.0332 (3)
C6	0.9424 (5)	0.75403 (10)	0.21242 (8)	0.0363 (4)
C7	1.1066 (5)	0.68363 (11)	0.24435 (9)	0.0397 (4)
C8	1.1756 (6)	0.68705 (11)	0.30786 (9)	0.0414 (4)
C9	1.0842 (6)	0.75963 (12)	0.34448 (8)	0.0398 (4)
C10	0.9247 (5)	0.82601 (10)	0.31526 (8)	0.0321 (3)
C11	0.7932 (6)	0.90675 (10)	0.34770 (7)	0.0386 (4)
O1W	0.5775 (11)	0.18936 (16)	1.01198 (10)	0.1069 (12)	0.85
H1W1	0.5888	0.1576	0.9790	0.101 (14)*	0.85
H2W1	0.4401	0.2303	1.0216	0.109 (17)*	0.85
H1	−0.012 (6)	1.0566 (13)	1.0558 (9)	0.040 (5)*
H3	0.416 (6)	0.8069 (14)	0.9779 (9)	0.044 (6)*
H4	0.474 (6)	0.8348 (12)	1.0870 (8)	0.032 (5)*
H8	1.274 (6)	0.6427 (13)	0.3299 (9)	0.049 (6)*
H9	1.141 (9)	0.7623 (15)	0.3865 (11)	0.065 (7)*
H7	1.155 (7)	0.6344 (12)	0.2193 (9)	0.042 (5)*
H1N1	−0.068 (6)	1.0297 (13)	0.9520 (10)	0.046 (6)*
H1N2	0.222 (7)	0.8578 (14)	0.8740 (10)	0.048 (6)*
H2N2	0.050 (7)	0.9426 (17)	0.8691 (11)	0.057 (7)*
H1N3	0.771 (6)	0.8649 (13)	0.2351 (9)	0.043 (6)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0578 (3)	0.0516 (2)	0.0353 (2)	−0.0024 (2)	−0.0049 (2)	−0.00042 (17)
N1	0.0431 (8)	0.0311 (6)	0.0331 (7)	0.0030 (6)	0.0011 (6)	0.0030 (5)
N2	0.0696 (13)	0.0352 (7)	0.0370 (7)	0.0118 (8)	−0.0039 (8)	−0.0020 (6)
C1	0.0429 (9)	0.0308 (7)	0.0358 (8)	0.0003 (7)	0.0029 (7)	0.0006 (6)
C2	0.0368 (8)	0.0298 (7)	0.0352 (7)	−0.0011 (7)	0.0018 (8)	0.0024 (6)
C3	0.0400 (9)	0.0302 (7)	0.0432 (8)	0.0033 (7)	−0.0002 (8)	0.0020 (6)
C4	0.0372 (9)	0.0358 (8)	0.0435 (9)	0.0001 (8)	−0.0030 (8)	0.0099 (7)
C5	0.0370 (9)	0.0383 (8)	0.0329 (7)	−0.0048 (7)	−0.0002 (7)	0.0029 (6)
O1	0.0731 (10)	0.0412 (6)	0.0306 (5)	0.0021 (7)	−0.0036 (7)	−0.0059 (5)
O2	0.0771 (11)	0.0396 (6)	0.0414 (6)	0.0175 (7)	−0.0040 (8)	−0.0052 (5)
O3	0.0709 (10)	0.0500 (7)	0.0339 (6)	0.0190 (8)	−0.0034 (8)	−0.0099 (5)
N3	0.0434 (8)	0.0265 (6)	0.0297 (6)	0.0026 (6)	−0.0020 (6)	0.0002 (5)
C6	0.0427 (9)	0.0324 (7)	0.0338 (7)	−0.0044 (7)	0.0038 (8)	−0.0036 (6)
C7	0.0440 (10)	0.0321 (7)	0.0429 (9)	0.0048 (8)	0.0060 (8)	−0.0045 (7)
C8	0.0445 (10)	0.0368 (8)	0.0430 (9)	0.0099 (8)	0.0017 (9)	0.0057 (7)
C9	0.0447 (10)	0.0421 (8)	0.0325 (8)	0.0040 (8)	−0.0020 (8)	0.0005 (7)
C10	0.0330 (8)	0.0334 (7)	0.0300 (7)	−0.0012 (7)	0.0024 (7)	−0.0026 (6)
C11	0.0466 (10)	0.0357 (7)	0.0335 (7)	0.0030 (8)	−0.0001 (8)	−0.0054 (6)
O1W	0.187 (4)	0.0767 (15)	0.0574 (12)	0.013 (2)	−0.0226 (18)	−0.0259 (11)

Cl1—C5	1.7331 (16)	O2—C11	1.237 (2)
N1—C2	1.348 (2)	O3—C11	1.2633 (18)
N1—C1	1.365 (2)	N3—C10	1.362 (2)
N1—H1N1	0.97 (2)	N3—C6	1.375 (2)
N2—C2	1.322 (2)	N3—H1N3	0.82 (2)
N2—H1N2	0.87 (2)	C6—C7	1.430 (3)
N2—H2N2	0.84 (3)	C7—C8	1.356 (3)
C1—C5	1.351 (2)	C7—H7	0.95 (2)
C1—H1	0.90 (2)	C8—C9	1.411 (3)
C2—C3	1.415 (2)	C8—H8	0.91 (2)
C3—C4	1.363 (3)	C9—C10	1.348 (2)
C3—H3	0.89 (2)	C9—H9	0.91 (2)
C4—C5	1.407 (2)	C10—C11	1.516 (2)
C4—H4	0.925 (19)	O1W—H1W1	0.85
O1—C6	1.2506 (19)	O1W—H2W1	0.85
C2—N1—C1	122.55 (14)	C10—N3—H1N3	116.4 (14)
C2—N1—H1N1	118.2 (12)	C6—N3—H1N3	118.4 (14)
C1—N1—H1N1	119.3 (12)	O1—C6—N3	119.75 (16)
C2—N2—H1N2	119.8 (15)	O1—C6—C7	125.67 (15)
C2—N2—H2N2	119.1 (16)	N3—C6—C7	114.58 (15)
H1N2—N2—H2N2	120 (2)	C8—C7—C6	120.84 (16)
C5—C1—N1	119.97 (16)	C8—C7—H7	122.4 (12)
C5—C1—H1	124.8 (12)	C6—C7—H7	116.7 (12)
N1—C1—H1	115.1 (12)	C7—C8—C9	121.09 (17)
N2—C2—N1	118.97 (15)	C7—C8—H8	123.0 (13)
N2—C2—C3	123.30 (16)	C9—C8—H8	115.8 (13)
N1—C2—C3	117.72 (15)	C10—C9—C8	118.78 (15)
C4—C3—C2	120.72 (16)	C10—C9—H9	120.8 (16)
C4—C3—H3	121.2 (13)	C8—C9—H9	120.4 (17)
C2—C3—H3	118.0 (13)	C9—C10—N3	119.51 (15)
C3—C4—C5	118.93 (16)	C9—C10—C11	125.75 (15)
C3—C4—H4	123.4 (11)	N3—C10—C11	114.73 (14)
C5—C4—H4	117.6 (11)	O2—C11—O3	126.89 (15)
C1—C5—C4	120.07 (16)	O2—C11—C10	117.57 (14)
C1—C5—Cl1	119.85 (13)	O3—C11—C10	115.51 (15)
C4—C5—Cl1	120.09 (13)	H1W1—O1W—H2W1	131.4
C10—N3—C6	125.17 (15)
C2—N1—C1—C5	−0.7 (3)	O1—C6—C7—C8	−180.0 (2)
C1—N1—C2—N2	−179.18 (19)	N3—C6—C7—C8	−0.4 (3)
C1—N1—C2—C3	1.8 (3)	C6—C7—C8—C9	0.7 (3)
N2—C2—C3—C4	179.8 (2)	C7—C8—C9—C10	0.3 (3)
N1—C2—C3—C4	−1.2 (3)	C8—C9—C10—N3	−1.5 (3)
C2—C3—C4—C5	−0.5 (3)	C8—C9—C10—C11	176.86 (19)
N1—C1—C5—C4	−1.1 (3)	C6—N3—C10—C9	1.8 (3)
N1—C1—C5—Cl1	178.92 (14)	C6—N3—C10—C11	−176.69 (18)
C3—C4—C5—C1	1.7 (3)	C9—C10—C11—O2	179.9 (2)
C3—C4—C5—Cl1	−178.37 (16)	N3—C10—C11—O2	−1.7 (3)
C10—N3—C6—O1	178.73 (18)	C9—C10—C11—O3	−1.6 (3)
C10—N3—C6—C7	−0.8 (3)	N3—C10—C11—O3	176.80 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O3i	0.85	1.85	2.696 (3)	174
O1W—H2W1···O1Wii	0.85	1.99	2.732 (5)	145
N1—H1N1···O3iii	0.98 (2)	1.67 (2)	2.637 (2)	170 (2)
N2—H1N2···O1iv	0.87 (2)	1.97 (2)	2.823 (2)	168 (2)
N2—H2N2···O2iii	0.84 (3)	2.04 (3)	2.882 (2)	179 (3)
C4—H4···O1v	0.93 (2)	2.39 (2)	3.296 (2)	166 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯O3i	0.85	1.85	2.696 (3)	174
O1W—H2W1⋯O1Wii	0.85	1.99	2.732 (5)	145
N1—H1N1⋯O3iii	0.98 (2)	1.67 (2)	2.637 (2)	170 (2)
N2—H1N2⋯O1iv	0.87 (2)	1.97 (2)	2.823 (2)	168 (2)
N2—H2N2⋯O2iii	0.84 (3)	2.04 (3)	2.882 (2)	179 (3)
C4—H4⋯O1v	0.93 (2)	2.39 (2)	3.296 (2)	166 (2)

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