Acta Cryst. (2011). E67, o488 [ doi:10.1107/S1600536811002248 ]
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-HO, O-HN and O-HO hydrogen bonds link the zwitterions and water molecules into sheets parallel to (102).
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.
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).
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).
![[Figure 1]](./cv5038fig1thm.gif)
| Fig. 1. View of (I) showing the atomic numbering and 30% probabilty displacement ellipsoids. |
![[Figure 2]](./cv5038fig2thm.gif)
| Fig. 2. Portion of the crystal packing showing the sheet of hydrogen-bonded (dashed lines) molecules. |
| 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 |
| C10H7N3O4·H2O | V = 1008.2 (8) Å3 |
| Mr = 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)° |
| 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 = 0.967 | Rint = 0.028 |
| 5038 measured reflections | θmax = 25.1° |
| R[F2 > 2σ(F2)] = 0.042 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.119 | Δρmax = 0.21 e Å−3 |
| S = 1.14 | Δρmin = −0.18 e Å−3 |
| 1777 reflections | Absolute structure: ? |
| 179 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
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 |
| 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. |
| 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. |
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Sun, T., Ma, J.-P., Huang, R.-Q. & Dong, Y.-B. (2006). Acta Cryst. E62, o2751–o2752.
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.