3-(4-Carb­oxy-5-carboxyl­ato-1H-imidazol-2-yl)pyridin-1-ium monohydrate

Liu, G.-J.; Zhao, G.-W.; Li, L.; Gao, H.-T.

doi:10.1107/S1600536811002248

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o488

doi:10.1107/S1600536811002248

Open

access

3-(4-Carboxy-5-carboxylato-1H-imidazol-2-yl)pyridin-1-ium monohydrate

Guang-Jun Liu,^a Guang-Wang Zhao,^a Li Li ^b and Hong-Tao Gao ^a ^*

^aDepartment of Chemisry and Chemical Engineering, Jining University, 273155 Qufu, Shandong, People's Republic of China, and ^bShandong Lukang Pharmaceutical Group Co. Ltd, 272100 Jining, Shandong, People's Republic of China
^*Correspondence e-mail: gaohongtao@gmail.com

(Received 10 January 2011; accepted 14 January 2011; online 26 January 2011)

In the zwitterionic molecule of the title compound, C₁₀H₇N₃O₄·H₂O, 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, intermolecular N—H⋯O, O—H⋯N and O—H⋯O hydrogen bonds link the zwitterions and water molecules 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_r = 251.20
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.042
wR(F²) = 0.119
S = 1.14
1777 reflections
179 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.18 e Å⁻³

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) -x+3, -y+2, -z+1; (ii) $[x+1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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.

Supporting information

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

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

checkCIF report

Comment top

Imidazole-4,5-dicarboxylic acid derivatives are recognized as efficient N,O-donors exhibiting diverse modes of coordination (Sun et al., 2006; Chen, 2008; Liu et al., 2009). In order to search for new derivatives of imidazole-4,5-dicarboxylic acid, the title compound (I) was synthesized and its crystal structure is reported here.

In (I) (Fig. 1), all bond lengths and angles are normal (Allen et al., 1987). The C4-containing carboxyl group is deprotonated and forms an intramolecular hydrogen bond with the neighboring C1-containing carboxyl group. The dihedral angle formed by imidazole ring and pyridinium ring is 5.23 (1) °. In the crystal structure, intermolecular N—H···O, O—H···N and O—H···O hydrogen bonds (Table 1) link the molecules into sheets parallel to (102) plane (Fig. 2). The short axis a of 3.7342 (18) Å suggests a presence of π-π interactions between the rings from the neighbouring sheets, which consolidate further the crystal packing.

Related literature top

For the use of the multifunctional connector 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 top

The title compound was synthesized according to the method reported in the literature (Lebedev et al., 2007). Yellow single crystals suitable for X-ray diffraction were obtained by slow evaporation of an acetonitrile solution of the compound.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. View of (I) showing the atomic numbering and 30% probabilty displacement ellipsoids.
	Fig. 2. Portion of the crystal packing showing the sheet of hydrogen-bonded (dashed lines) molecules.

3-(4-Carboxy-5-carboxylato-1H-imidazol-2-yl)pyridin-1-ium monohydrate top

Crystal data top

C₁₀H₇N₃O₄·H₂O	F(000) = 520
M_r = 251.20	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0612P)²] where P = (F_o² + 2F_c²)/3
1777 reflections	(Δ/σ)_max < 0.001
179 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₀H₇N₃O₄·H₂O	V = 1008.2 (8) Å³
M_r = 251.20	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 3.7342 (18) Å	µ = 0.14 mm⁻¹
b = 16.354 (8) Å	T = 298 K
c = 16.634 (8) Å	0.32 × 0.28 × 0.25 mm
β = 97.019 (10)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	1777 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1314 reflections with I > 2σ(I)
T_min = 0.958, T_max = 0.967	R_int = 0.028
5038 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	Δρ_max = 0.21 e Å⁻³
1777 reflections	Δρ_min = −0.18 e Å⁻³
179 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+3, −y+2, −z+1; (ii) x+1, −y+3/2, z+1/2; (iii) −x+2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₀H₇N₃O₄·H₂O
M_r	251.20
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	3.7342 (18), 16.354 (8), 16.634 (8)
β (°)	97.019 (10)
V (Å³)	1008.2 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.14
Crystal size (mm)	0.32 × 0.28 × 0.25

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.958, 0.967
No. of measured, independent and observed [I > 2σ(I)] reflections	5038, 1777, 1314
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.119, 1.14
No. of reflections	1777
No. of parameters	179
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.18

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) −x+3, −y+2, −z+1; (ii) x+1, −y+3/2, z+1/2; (iii) −x+2, y−1/2, −z+1/2.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, L.-Z. (2008). Acta Cryst. E64, m1286. Web of Science CSD CrossRef IUCr Journals Google Scholar
Lebedev, A. V., Lebedev, A. B., Sheludyakov, V. D., Kovaleva, E. A., Ustinova, O. L. & Shatunov, V. V. (2007). Russ. J. Gen. Chem. 77, 949–953. Web of Science CrossRef CAS Google Scholar
Liu, W., Zhang, G., Li, X., Wu, B.-L. & Zhang, H.-Y. (2009). Acta Cryst. E65, m938–m939. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sun, T., Ma, J.-P., Huang, R.-Q. & Dong, Y.-B. (2006). Acta Cryst. E62, o2751–o2752. Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o488

doi:10.1107/S1600536811002248

Open

access