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ISSN: 2056-9890

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

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[Sun, T., Ma, J.-P., Huang, R.-Q. & Dong, Y.-B. (2006). Acta Cryst. E62, o2751-o2752.]); Chen (2008[Chen, L.-Z. (2008). Acta Cryst. E64, m1286.]); Liu et al. (2009[Liu, W., Zhang, G., Li, X., Wu, B.-L. & Zhang, H.-Y. (2009). Acta Cryst. E65, m938-m939.]). For the synthesis of the title compound, see: Lebedev et al. (2007[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.]). For bond-length data, see: Allen et al. (1987[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.]).

[Scheme 1]

Experimental

Crystal data
  • C10H7N3O4·H2O

  • Mr = 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[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.958, Tmax = 0.967

  • 5038 measured reflections

  • 1777 independent reflections

  • 1314 reflections with I > 2σ(I)

  • Rint = 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

  • Δρmax = 0.21 e Å−3

  • Δρmin = −0.18 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


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.

Refinement top

H atoms bonded to N and O atoms were located in a difference Fourier map and refined isotropically. C-bound H atoms were placed in calculated positions with C—H = 0.93 Å, and refined as riding, with Uiso(H) = 1.2Uiso(C).

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
[Figure 1] Fig. 1. View of (I) showing the atomic numbering and 30% probabilty displacement ellipsoids.
[Figure 2] 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·H2OF(000) = 520
Mr = 251.20Dx = 1.655 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1155 reflections
a = 3.7342 (18) Åθ = 2.5–21.9°
b = 16.354 (8) ŵ = 0.14 mm1
c = 16.634 (8) ÅT = 298 K
β = 97.019 (10)°Block, yellow
V = 1008.2 (8) Å30.32 × 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 tube1314 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
ϕ and ω scansθmax = 25.1°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
h = 44
Tmin = 0.958, Tmax = 0.967k = 1819
5038 measured reflectionsl = 1915
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119H 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 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.18 e Å3
Crystal data top
C10H7N3O4·H2OV = 1008.2 (8) Å3
Mr = 251.20Z = 4
Monoclinic, P21/cMo Kα radiation
a = 3.7342 (18) ŵ = 0.14 mm1
b = 16.354 (8) ÅT = 298 K
c = 16.634 (8) Å0.32 × 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)
Tmin = 0.958, Tmax = 0.967Rint = 0.028
5038 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0420 restraints
wR(F2) = 0.119H atoms treated by a mixture of independent and constrained refinement
S = 1.14Δρmax = 0.21 e Å3
1777 reflectionsΔρmin = 0.18 e Å3
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
xyzUiso*/Ueq
O10.5287 (5)0.93482 (10)0.16289 (9)0.0556 (5)
O20.7858 (5)1.05235 (10)0.19683 (9)0.0573 (5)
H20.91291.07210.23570.086*
O31.1698 (5)1.11399 (9)0.31442 (9)0.0576 (5)
O41.4072 (5)1.07667 (9)0.43806 (9)0.0525 (5)
N11.1259 (5)0.92199 (10)0.41497 (10)0.0348 (4)
N20.7955 (5)0.86368 (10)0.31150 (9)0.0356 (4)
N31.0972 (6)0.70365 (11)0.55425 (11)0.0455 (5)
C10.7137 (6)0.97627 (13)0.21234 (13)0.0415 (6)
C20.8660 (6)0.94325 (12)0.29214 (11)0.0347 (5)
C31.0711 (5)0.98027 (11)0.35661 (11)0.0335 (5)
C41.2301 (6)1.06322 (12)0.37174 (12)0.0391 (5)
C50.9577 (6)0.85300 (11)0.38601 (11)0.0329 (5)
C60.9521 (6)0.77649 (12)0.43184 (12)0.0338 (5)
C71.1011 (6)0.77284 (13)0.51242 (12)0.0396 (5)
H71.20500.81940.53750.047*
C80.7973 (6)0.70592 (13)0.39780 (13)0.0424 (6)
H80.69160.70620.34420.051*
C90.7986 (7)0.63518 (13)0.44279 (13)0.0466 (6)
H90.69450.58770.41970.056*
C100.9544 (7)0.63514 (14)0.52181 (13)0.0478 (6)
H100.95990.58750.55240.057*
O1W0.4229 (6)0.75493 (12)0.19730 (11)0.0711 (6)
H11.271 (5)0.9320 (11)0.4672 (12)0.032 (5)*
H31.211 (8)0.7089 (16)0.6111 (18)0.080 (9)*
H1B0.556 (12)0.797 (2)0.228 (2)0.143 (15)*
H1A0.570 (11)0.709 (2)0.193 (2)0.122 (13)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0640 (12)0.0629 (10)0.0351 (9)0.0017 (9)0.0135 (8)0.0030 (7)
O20.0700 (13)0.0532 (10)0.0441 (9)0.0053 (9)0.0114 (8)0.0136 (7)
O30.0715 (13)0.0442 (9)0.0524 (10)0.0060 (8)0.0111 (9)0.0120 (8)
O40.0650 (12)0.0457 (9)0.0419 (9)0.0067 (8)0.0127 (8)0.0030 (7)
N10.0393 (11)0.0355 (9)0.0286 (9)0.0006 (8)0.0004 (8)0.0026 (7)
N20.0354 (11)0.0405 (10)0.0298 (9)0.0014 (8)0.0001 (8)0.0026 (7)
N30.0547 (14)0.0490 (11)0.0312 (10)0.0002 (9)0.0017 (9)0.0036 (9)
C10.0408 (14)0.0468 (13)0.0363 (12)0.0044 (11)0.0021 (10)0.0003 (10)
C20.0340 (13)0.0389 (11)0.0313 (11)0.0053 (9)0.0048 (9)0.0008 (9)
C30.0330 (12)0.0355 (11)0.0314 (10)0.0047 (9)0.0018 (9)0.0015 (9)
C40.0400 (14)0.0394 (12)0.0373 (12)0.0049 (10)0.0021 (10)0.0019 (10)
C50.0331 (12)0.0358 (11)0.0292 (10)0.0027 (9)0.0013 (9)0.0044 (8)
C60.0296 (12)0.0385 (11)0.0331 (11)0.0028 (9)0.0027 (9)0.0015 (9)
C70.0409 (14)0.0401 (12)0.0366 (12)0.0007 (10)0.0005 (10)0.0009 (9)
C80.0451 (15)0.0466 (12)0.0337 (12)0.0034 (10)0.0027 (10)0.0026 (10)
C90.0492 (15)0.0401 (12)0.0501 (14)0.0070 (11)0.0045 (11)0.0059 (10)
C100.0524 (16)0.0460 (13)0.0447 (14)0.0051 (11)0.0044 (12)0.0052 (10)
O1W0.1032 (17)0.0470 (11)0.0534 (11)0.0091 (11)0.0304 (11)0.0099 (8)
Geometric parameters (Å, º) top
O1—C11.214 (2)C2—C31.379 (3)
O2—C11.305 (3)C3—C41.490 (3)
O2—H20.8201C5—C61.467 (3)
O3—C41.264 (2)C6—C81.381 (3)
O4—C41.235 (2)C6—C71.388 (3)
N1—C51.351 (2)C7—H70.9300
N1—C31.358 (3)C8—C91.377 (3)
N1—H10.98 (2)C8—H80.9300
N2—C51.323 (2)C9—C101.371 (3)
N2—C21.374 (3)C9—H90.9300
N3—C101.327 (3)C10—H100.9300
N3—C71.329 (3)O1W—H1B0.95 (4)
N3—H30.99 (3)O1W—H1A0.94 (4)
C1—C21.481 (3)
C1—O2—H2109.5N2—C5—N1111.31 (17)
C5—N1—C3107.96 (17)N2—C5—C6124.45 (18)
C5—N1—H1129.6 (10)N1—C5—C6124.24 (17)
C3—N1—H1122.4 (11)C8—C6—C7117.27 (19)
C5—N2—C2105.42 (16)C8—C6—C5122.13 (18)
C10—N3—C7122.4 (2)C7—C6—C5120.60 (18)
C10—N3—H3124.4 (16)N3—C7—C6120.88 (19)
C7—N3—H3113.2 (16)N3—C7—H7119.6
O1—C1—O2120.8 (2)C6—C7—H7119.6
O1—C1—C2121.9 (2)C9—C8—C6120.4 (2)
O2—C1—C2117.32 (19)C9—C8—H8119.8
N2—C2—C3109.74 (17)C6—C8—H8119.8
N2—C2—C1119.47 (18)C10—C9—C8119.6 (2)
C3—C2—C1130.76 (19)C10—C9—H9120.2
N1—C3—C2105.58 (17)C8—C9—H9120.2
N1—C3—C4119.74 (17)N3—C10—C9119.5 (2)
C2—C3—C4134.67 (18)N3—C10—H10120.3
O4—C4—O3125.7 (2)C9—C10—H10120.3
O4—C4—C3118.17 (18)H1B—O1W—H1A110 (4)
O3—C4—C3116.11 (18)
C5—N2—C2—C30.5 (2)C2—N2—C5—N10.3 (2)
C5—N2—C2—C1178.48 (19)C2—N2—C5—C6179.57 (19)
O1—C1—C2—N20.4 (3)C3—N1—C5—N20.1 (2)
O2—C1—C2—N2179.53 (19)C3—N1—C5—C6179.32 (19)
O1—C1—C2—C3178.0 (2)N2—C5—C6—C85.3 (3)
O2—C1—C2—C32.0 (4)N1—C5—C6—C8175.5 (2)
C5—N1—C3—C20.2 (2)N2—C5—C6—C7174.0 (2)
C5—N1—C3—C4179.47 (18)N1—C5—C6—C75.2 (3)
N2—C2—C3—N10.4 (2)C10—N3—C7—C60.3 (3)
C1—C2—C3—N1178.2 (2)C8—C6—C7—N30.8 (3)
N2—C2—C3—C4179.5 (2)C5—C6—C7—N3179.91 (19)
C1—C2—C3—C42.8 (4)C7—C6—C8—C90.9 (3)
N1—C3—C4—O40.5 (3)C5—C6—C8—C9179.8 (2)
C2—C3—C4—O4179.5 (2)C6—C8—C9—C100.1 (3)
N1—C3—C4—O3179.49 (19)C7—N3—C10—C91.2 (4)
C2—C3—C4—O30.5 (4)C8—C9—C10—N31.0 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O4i0.98 (2)1.87 (2)2.824 (3)164.8 (16)
N3—H3···O1Wii0.99 (3)1.66 (3)2.625 (3)163 (2)
O1W—H1A···O3iii0.94 (4)1.84 (4)2.782 (3)176 (4)
O1W—H1B···O10.95 (4)2.50 (4)3.032 (3)115 (3)
O1W—H1B···N20.95 (4)1.90 (4)2.839 (2)166 (3)
O2—H2···O30.821.672.493 (2)179
Symmetry codes: (i) x+3, y+2, z+1; (ii) x+1, y+3/2, z+1/2; (iii) x+2, y1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC10H7N3O4·H2O
Mr251.20
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)3.7342 (18), 16.354 (8), 16.634 (8)
β (°) 97.019 (10)
V3)1008.2 (8)
Z4
Radiation typeMo Kα
µ (mm1)0.14
Crystal size (mm)0.32 × 0.28 × 0.25
Data collection
DiffractometerBruker SMART APEX CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.958, 0.967
No. of measured, independent and
observed [I > 2σ(I)] reflections
5038, 1777, 1314
Rint0.028
(sin θ/λ)max1)0.596
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.119, 1.14
No. of reflections1777
No. of parameters179
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.21, 0.18

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

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O4i0.98 (2)1.87 (2)2.824 (3)164.8 (16)
N3—H3···O1Wii0.99 (3)1.66 (3)2.625 (3)163 (2)
O1W—H1A···O3iii0.94 (4)1.84 (4)2.782 (3)176 (4)
O1W—H1B···O10.95 (4)2.50 (4)3.032 (3)115 (3)
O1W—H1B···N20.95 (4)1.90 (4)2.839 (2)166 (3)
O2—H2···O30.821.672.493 (2)179
Symmetry codes: (i) x+3, y+2, z+1; (ii) x+1, y+3/2, z+1/2; (iii) x+2, y1/2, z+1/2.
 

References

First citationAllen, 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
First citationBruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationChen, L.-Z. (2008). Acta Cryst. E64, m1286.  Web of Science CSD CrossRef IUCr Journals
First citationLebedev, 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
First citationLiu, W., Zhang, G., Li, X., Wu, B.-L. & Zhang, H.-Y. (2009). Acta Cryst. E65, m938–m939.  Web of Science CSD CrossRef IUCr Journals
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSun, T., Ma, J.-P., Huang, R.-Q. & Dong, Y.-B. (2006). Acta Cryst. E62, o2751–o2752.  Web of Science CSD CrossRef IUCr Journals

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