3-(4-Carb-oxy-5-carboxyl-ato-1H-imidazol-2-yl)pyridin-1-ium monohydrate.

In the zwitterionic mol-ecule of the title compound, C(10)H(7)N(3)O(4)·H(2)O, one carboxyl group is deprotonated and the pyridine N atom is protonated. The pyridinium and imidazole rings form a dihedral angle of 5.23 (1)°. An intramolecular O-H⋯O hydrogen bond occurs. In the crystal, inter-molecular N-H⋯O, O-H⋯N and O-H⋯O hydrogen bonds link the zwitterions and water mol-ecules into sheets parallel to (102).

Related literature

For the use of 4,5-imidazole­dicarb­oxy­lic acid in coordination chemistry and for related structures, see: Sun et al. (2006 ▶); Chen (2008 ▶); Liu et al. (2009 ▶). For the synthesis of the title compound, see: Lebedev et al. (2007 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C10H7N3O4·H2O

M = 251.20

Monoclinic,

a = 3.7342 (18) Å

b = 16.354 (8) Å

c = 16.634 (8) Å

β = 97.019 (10)°

V = 1008.2 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.14 mm−1

T = 298 K

0.32 × 0.28 × 0.25 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.958, T max = 0.967

5038 measured reflections

1777 independent reflections

1314 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.119

S = 1.14

1777 reflections

179 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811002248/cv5038sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811002248/cv5038Isup2.hkl

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

C10H7N3O4·H2O	F(000) = 520
Mr = 251.20	Dx = 1.655 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1155 reflections
a = 3.7342 (18) Å	θ = 2.5–21.9°
b = 16.354 (8) Å	µ = 0.14 mm−1
c = 16.634 (8) Å	T = 298 K
β = 97.019 (10)°	Block, yellow
V = 1008.2 (8) Å3	0.32 × 0.28 × 0.25 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	1777 independent reflections
Radiation source: fine-focus sealed tube	1314 reflections with I > 2σ(I)
graphite	Rint = 0.028
φ and ω scans	θmax = 25.1°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −4→4
Tmin = 0.958, Tmax = 0.967	k = −18→19
5038 measured reflections	l = −19→15

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	w = 1/[σ2(Fo2) + (0.0612P)2] where P = (Fo2 + 2Fc2)/3
1777 reflections	(Δ/σ)max < 0.001
179 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.18 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
O1	0.5287 (5)	0.93482 (10)	0.16289 (9)	0.0556 (5)
O2	0.7858 (5)	1.05235 (10)	0.19683 (9)	0.0573 (5)
H2	0.9129	1.0721	0.2357	0.086*
O3	1.1698 (5)	1.11399 (9)	0.31442 (9)	0.0576 (5)
O4	1.4072 (5)	1.07667 (9)	0.43806 (9)	0.0525 (5)
N1	1.1259 (5)	0.92199 (10)	0.41497 (10)	0.0348 (4)
N2	0.7955 (5)	0.86368 (10)	0.31150 (9)	0.0356 (4)
N3	1.0972 (6)	0.70365 (11)	0.55425 (11)	0.0455 (5)
C1	0.7137 (6)	0.97627 (13)	0.21234 (13)	0.0415 (6)
C2	0.8660 (6)	0.94325 (12)	0.29214 (11)	0.0347 (5)
C3	1.0711 (5)	0.98027 (11)	0.35661 (11)	0.0335 (5)
C4	1.2301 (6)	1.06322 (12)	0.37174 (12)	0.0391 (5)
C5	0.9577 (6)	0.85300 (11)	0.38601 (11)	0.0329 (5)
C6	0.9521 (6)	0.77649 (12)	0.43184 (12)	0.0338 (5)
C7	1.1011 (6)	0.77284 (13)	0.51242 (12)	0.0396 (5)
H7	1.2050	0.8194	0.5375	0.047*
C8	0.7973 (6)	0.70592 (13)	0.39780 (13)	0.0424 (6)
H8	0.6916	0.7062	0.3442	0.051*
C9	0.7986 (7)	0.63518 (13)	0.44279 (13)	0.0466 (6)
H9	0.6945	0.5877	0.4197	0.056*
C10	0.9544 (7)	0.63514 (14)	0.52181 (13)	0.0478 (6)
H10	0.9599	0.5875	0.5524	0.057*
O1W	0.4229 (6)	0.75493 (12)	0.19730 (11)	0.0711 (6)
H1	1.271 (5)	0.9320 (11)	0.4672 (12)	0.032 (5)*
H3	1.211 (8)	0.7089 (16)	0.6111 (18)	0.080 (9)*
H1B	0.556 (12)	0.797 (2)	0.228 (2)	0.143 (15)*
H1A	0.570 (11)	0.709 (2)	0.193 (2)	0.122 (13)*

	U11	U22	U33	U12	U13	U23
O1	0.0640 (12)	0.0629 (10)	0.0351 (9)	−0.0017 (9)	−0.0135 (8)	−0.0030 (7)
O2	0.0700 (13)	0.0532 (10)	0.0441 (9)	−0.0053 (9)	−0.0114 (8)	0.0136 (7)
O3	0.0715 (13)	0.0442 (9)	0.0524 (10)	−0.0060 (8)	−0.0111 (9)	0.0120 (8)
O4	0.0650 (12)	0.0457 (9)	0.0419 (9)	−0.0067 (8)	−0.0127 (8)	−0.0030 (7)
N1	0.0393 (11)	0.0355 (9)	0.0286 (9)	−0.0006 (8)	0.0004 (8)	−0.0026 (7)
N2	0.0354 (11)	0.0405 (10)	0.0298 (9)	0.0014 (8)	−0.0001 (8)	−0.0026 (7)
N3	0.0547 (14)	0.0490 (11)	0.0312 (10)	0.0002 (9)	−0.0017 (9)	0.0036 (9)
C1	0.0408 (14)	0.0468 (13)	0.0363 (12)	0.0044 (11)	0.0021 (10)	−0.0003 (10)
C2	0.0340 (13)	0.0389 (11)	0.0313 (11)	0.0053 (9)	0.0048 (9)	0.0008 (9)
C3	0.0330 (12)	0.0355 (11)	0.0314 (10)	0.0047 (9)	0.0018 (9)	−0.0015 (9)
C4	0.0400 (14)	0.0394 (12)	0.0373 (12)	0.0049 (10)	0.0021 (10)	0.0019 (10)
C5	0.0331 (12)	0.0358 (11)	0.0292 (10)	0.0027 (9)	0.0013 (9)	−0.0044 (8)
C6	0.0296 (12)	0.0385 (11)	0.0331 (11)	0.0028 (9)	0.0027 (9)	−0.0015 (9)
C7	0.0409 (14)	0.0401 (12)	0.0366 (12)	−0.0007 (10)	0.0005 (10)	−0.0009 (9)
C8	0.0451 (15)	0.0466 (12)	0.0337 (12)	−0.0034 (10)	−0.0027 (10)	−0.0026 (10)
C9	0.0492 (15)	0.0401 (12)	0.0501 (14)	−0.0070 (11)	0.0045 (11)	−0.0059 (10)
C10	0.0524 (16)	0.0460 (13)	0.0447 (14)	−0.0051 (11)	0.0044 (12)	0.0052 (10)
O1W	0.1032 (17)	0.0470 (11)	0.0534 (11)	0.0091 (11)	−0.0304 (11)	−0.0099 (8)

O1—C1	1.214 (2)	C2—C3	1.379 (3)
O2—C1	1.305 (3)	C3—C4	1.490 (3)
O2—H2	0.8201	C5—C6	1.467 (3)
O3—C4	1.264 (2)	C6—C8	1.381 (3)
O4—C4	1.235 (2)	C6—C7	1.388 (3)
N1—C5	1.351 (2)	C7—H7	0.9300
N1—C3	1.358 (3)	C8—C9	1.377 (3)
N1—H1	0.98 (2)	C8—H8	0.9300
N2—C5	1.323 (2)	C9—C10	1.371 (3)
N2—C2	1.374 (3)	C9—H9	0.9300
N3—C10	1.327 (3)	C10—H10	0.9300
N3—C7	1.329 (3)	O1W—H1B	0.95 (4)
N3—H3	0.99 (3)	O1W—H1A	0.94 (4)
C1—C2	1.481 (3)
C1—O2—H2	109.5	N2—C5—N1	111.31 (17)
C5—N1—C3	107.96 (17)	N2—C5—C6	124.45 (18)
C5—N1—H1	129.6 (10)	N1—C5—C6	124.24 (17)
C3—N1—H1	122.4 (11)	C8—C6—C7	117.27 (19)
C5—N2—C2	105.42 (16)	C8—C6—C5	122.13 (18)
C10—N3—C7	122.4 (2)	C7—C6—C5	120.60 (18)
C10—N3—H3	124.4 (16)	N3—C7—C6	120.88 (19)
C7—N3—H3	113.2 (16)	N3—C7—H7	119.6
O1—C1—O2	120.8 (2)	C6—C7—H7	119.6
O1—C1—C2	121.9 (2)	C9—C8—C6	120.4 (2)
O2—C1—C2	117.32 (19)	C9—C8—H8	119.8
N2—C2—C3	109.74 (17)	C6—C8—H8	119.8
N2—C2—C1	119.47 (18)	C10—C9—C8	119.6 (2)
C3—C2—C1	130.76 (19)	C10—C9—H9	120.2
N1—C3—C2	105.58 (17)	C8—C9—H9	120.2
N1—C3—C4	119.74 (17)	N3—C10—C9	119.5 (2)
C2—C3—C4	134.67 (18)	N3—C10—H10	120.3
O4—C4—O3	125.7 (2)	C9—C10—H10	120.3
O4—C4—C3	118.17 (18)	H1B—O1W—H1A	110 (4)
O3—C4—C3	116.11 (18)
C5—N2—C2—C3	−0.5 (2)	C2—N2—C5—N1	0.3 (2)
C5—N2—C2—C1	−178.48 (19)	C2—N2—C5—C6	179.57 (19)
O1—C1—C2—N2	−0.4 (3)	C3—N1—C5—N2	−0.1 (2)
O2—C1—C2—N2	179.53 (19)	C3—N1—C5—C6	−179.32 (19)
O1—C1—C2—C3	−178.0 (2)	N2—C5—C6—C8	5.3 (3)
O2—C1—C2—C3	2.0 (4)	N1—C5—C6—C8	−175.5 (2)
C5—N1—C3—C2	−0.2 (2)	N2—C5—C6—C7	−174.0 (2)
C5—N1—C3—C4	−179.47 (18)	N1—C5—C6—C7	5.2 (3)
N2—C2—C3—N1	0.4 (2)	C10—N3—C7—C6	0.3 (3)
C1—C2—C3—N1	178.2 (2)	C8—C6—C7—N3	0.8 (3)
N2—C2—C3—C4	179.5 (2)	C5—C6—C7—N3	−179.91 (19)
C1—C2—C3—C4	−2.8 (4)	C7—C6—C8—C9	−0.9 (3)
N1—C3—C4—O4	−0.5 (3)	C5—C6—C8—C9	179.8 (2)
C2—C3—C4—O4	−179.5 (2)	C6—C8—C9—C10	0.1 (3)
N1—C3—C4—O3	179.49 (19)	C7—N3—C10—C9	−1.2 (4)
C2—C3—C4—O3	0.5 (4)	C8—C9—C10—N3	1.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4i	0.98 (2)	1.87 (2)	2.824 (3)	164.8 (16)
N3—H3···O1Wii	0.99 (3)	1.66 (3)	2.625 (3)	163 (2)
O1W—H1A···O3iii	0.94 (4)	1.84 (4)	2.782 (3)	176 (4)
O1W—H1B···O1	0.95 (4)	2.50 (4)	3.032 (3)	115 (3)
O1W—H1B···N2	0.95 (4)	1.90 (4)	2.839 (2)	166 (3)
O2—H2···O3	0.82	1.67	2.493 (2)	179

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O4i	0.98 (2)	1.87 (2)	2.824 (3)	164.8 (16)
N3—H3⋯O1Wii	0.99 (3)	1.66 (3)	2.625 (3)	163 (2)
O1W—H1A⋯O3iii	0.94 (4)	1.84 (4)	2.782 (3)	176 (4)
O1W—H1B⋯O1	0.95 (4)	2.50 (4)	3.032 (3)	115 (3)
O1W—H1B⋯N2	0.95 (4)	1.90 (4)	2.839 (2)	166 (3)
O2—H2⋯O3	0.82	1.67	2.493 (2)	179

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