Acta Cryst. (2008). E64, o1110 [ doi:10.1107/S1600536808014013 ]
Planar molecules of the title compound, C3H4N4O, are organized into sheets by extensive N-H
O and N-HN hydrogen bonding in the (101) plane of the crystal structure. These hydrogen bonds may also stabilize the molecule in the Z form. The title compound is in the amide form, as shown by the C=O bond length [1.252 (2) Å].
Added 20 ml 25% ammonium hydroxide to methyl 1H-1,2,4-triazole-3-carboxylate (20 mmol, 2540 mg) while stirring for 8 h at 353 K. The resulting white precipitate was filtered and washed several times with ethanol and dried in vacuo (yield 85%). Single crystals of C3H4N4O suitable for X-ray diffraction were obtained by slow evaporation of an 50% ethanol solution at room temperature over a period of one week.
The C– and N-bound H atoms were placed in calculated positions and included in the refinement in the riding-model approximation with N—H = 0.86 Å and C—H = 0.93 Å, and with Uiso(H) 1.2Ueq(C,N).
Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
![[Figure 1]](./cs2075fig1thm.gif)
| Fig. 1. The structure of the title compound showing 30% probability displacement ellipsoids and the atom-numbering scheme. |
![[Figure 2]](./cs2075fig2thm.gif)
| Fig. 2. Crystal packing showing the hydrogen bonded interactions as dashed lines. |
| C3H4N4O | F000 = 232 |
| Mr = 112.10 | Dx = 1.636 Mg m−3 |
| Monoclinic, P21/n | Mo Kα radiation λ = 0.71073 Å |
| Hall symbol: -P 2yn | Cell parameters from 1200 reflections |
| a = 3.6944 (4) Å | θ = 2.3–27.5º |
| b = 17.527 (3) Å | µ = 0.13 mm−1 |
| c = 7.0520 (17) Å | T = 298 (2) K |
| β = 94.4670 (10)º | Prism, colourless |
| V = 455.24 (14) Å3 | 0.22 × 0.18 × 0.09 mm |
| Z = 4 |
| Bruker SMART CCD diffractometer | 807 independent reflections |
| Radiation source: fine-focus sealed tube | 657 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.020 |
| T = 298(2) K | θmax = 25.0º |
| φ and ω scans | θmin = 2.3º |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −4→3 |
| Tmin = 0.972, Tmax = 0.988 | k = −20→18 |
| 2199 measured reflections | l = −8→8 |
| 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)] = 0.035 | H-atom parameters constrained |
| wR(F2) = 0.101 | w = 1/[σ2(Fo2) + (0.0653P)2 + 0.058P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.05 | (Δ/σ)max < 0.001 |
| 807 reflections | Δρmax = 0.13 e Å−3 |
| 73 parameters | Δρmin = −0.23 e Å−3 |
| Primary atom site location: structure-invariant direct methods | Extinction correction: none |
| C3H4N4O | V = 455.24 (14) Å3 |
| Mr = 112.10 | Z = 4 |
| Monoclinic, P21/n | Mo Kα |
| a = 3.6944 (4) Å | µ = 0.13 mm−1 |
| b = 17.527 (3) Å | T = 298 (2) K |
| c = 7.0520 (17) Å | 0.22 × 0.18 × 0.09 mm |
| β = 94.4670 (10)º |
| Bruker SMART CCD diffractometer | 807 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 657 reflections with I > 2σ(I) |
| Tmin = 0.972, Tmax = 0.988 | Rint = 0.020 |
| 2199 measured reflections |
| R[F2 > 2σ(F2)] = 0.035 | 73 parameters |
| wR(F2) = 0.101 | H-atom parameters constrained |
| S = 1.05 | Δρmax = 0.13 e Å−3 |
| 807 reflections | Δρmin = −0.23 e Å−3 |
| x | y | z | Uiso*/Ueq | ||
| N1 | 0.2702 (4) | 0.99272 (7) | 0.7168 (2) | 0.0381 (4) | |
| H1A | 0.3404 | 1.0240 | 0.6332 | 0.046* | |
| H1B | 0.1763 | 1.0098 | 0.8163 | 0.046* | |
| N2 | 0.0498 (4) | 0.77481 (8) | 1.00884 (19) | 0.0330 (4) | |
| H2 | 0.0162 | 0.7288 | 1.0460 | 0.040* | |
| N3 | 0.1784 (4) | 0.79443 (7) | 0.84073 (18) | 0.0329 (4) | |
| N4 | 0.0595 (4) | 0.89955 (8) | 1.01228 (18) | 0.0349 (4) | |
| O1 | 0.4402 (3) | 0.88844 (6) | 0.55202 (16) | 0.0386 (4) | |
| C1 | 0.3067 (4) | 0.91813 (8) | 0.6923 (2) | 0.0289 (4) | |
| C2 | 0.1793 (4) | 0.87021 (8) | 0.8491 (2) | 0.0271 (4) | |
| C3 | −0.0168 (5) | 0.83716 (9) | 1.1079 (2) | 0.0360 (4) | |
| H3 | −0.1048 | 0.8370 | 1.2279 | 0.043* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| N1 | 0.0594 (10) | 0.0241 (8) | 0.0333 (8) | 0.0011 (6) | 0.0202 (7) | 0.0017 (5) |
| N2 | 0.0449 (9) | 0.0220 (7) | 0.0331 (8) | −0.0010 (5) | 0.0098 (6) | 0.0056 (5) |
| N3 | 0.0434 (8) | 0.0250 (8) | 0.0314 (7) | −0.0006 (5) | 0.0093 (6) | 0.0010 (5) |
| N4 | 0.0494 (9) | 0.0259 (8) | 0.0310 (8) | 0.0004 (6) | 0.0145 (6) | 0.0004 (5) |
| O1 | 0.0566 (8) | 0.0267 (6) | 0.0347 (7) | 0.0030 (5) | 0.0176 (5) | −0.0001 (5) |
| C1 | 0.0339 (9) | 0.0259 (9) | 0.0274 (8) | 0.0006 (6) | 0.0055 (6) | −0.0007 (6) |
| C2 | 0.0307 (8) | 0.0243 (8) | 0.0268 (8) | 0.0016 (6) | 0.0052 (6) | −0.0009 (6) |
| C3 | 0.0495 (10) | 0.0292 (9) | 0.0308 (8) | −0.0012 (7) | 0.0131 (7) | 0.0013 (7) |
| N1—C1 | 1.3270 (19) | N3—C2 | 1.3294 (19) |
| N1—H1A | 0.8600 | N4—C3 | 1.326 (2) |
| N1—H1B | 0.8600 | N4—C2 | 1.366 (2) |
| N2—C3 | 1.330 (2) | O1—C1 | 1.2524 (18) |
| N2—N3 | 1.3553 (19) | C1—C2 | 1.493 (2) |
| N2—H2 | 0.8600 | C3—H3 | 0.9300 |
| C1—N1—H1A | 120.0 | O1—C1—C2 | 121.15 (14) |
| C1—N1—H1B | 120.0 | N1—C1—C2 | 114.62 (14) |
| H1A—N1—H1B | 120.0 | N3—C2—N4 | 114.43 (13) |
| C3—N2—N3 | 110.03 (13) | N3—C2—C1 | 121.94 (13) |
| C3—N2—H2 | 125.0 | N4—C2—C1 | 123.62 (14) |
| N3—N2—H2 | 125.0 | N4—C3—N2 | 110.81 (15) |
| C2—N3—N2 | 102.40 (13) | N4—C3—H3 | 124.6 |
| C3—N4—C2 | 102.33 (13) | N2—C3—H3 | 124.6 |
| O1—C1—N1 | 124.23 (15) | ||
| C3—N2—N3—C2 | −0.33 (17) | N1—C1—C2—N3 | 176.10 (15) |
| N2—N3—C2—N4 | 0.05 (17) | O1—C1—C2—N4 | 174.46 (15) |
| N2—N3—C2—C1 | 179.30 (13) | N1—C1—C2—N4 | −4.7 (2) |
| C3—N4—C2—N3 | 0.23 (18) | C2—N4—C3—N2 | −0.43 (18) |
| C3—N4—C2—C1 | −179.00 (14) | N3—N2—C3—N4 | 0.50 (19) |
| O1—C1—C2—N3 | −4.7 (2) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1A···O1i | 0.86 | 2.21 | 3.065 (2) | 173 |
| N1—H1B···N4ii | 0.86 | 2.22 | 3.010 (2) | 154 |
| N2—H2···O1iii | 0.86 | 2.07 | 2.909 (2) | 163 |
| N2—H2···N3iii | 0.86 | 2.54 | 3.055 (2) | 120 |
| Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x, −y+2, −z+2; (iii) x−1/2, −y+3/2, z+1/2. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1A···O1i | 0.86 | 2.21 | 3.065 (2) | 173 |
| N1—H1B···N4ii | 0.86 | 2.22 | 3.010 (2) | 154 |
| N2—H2···O1iii | 0.86 | 2.07 | 2.909 (2) | 163 |
| N2—H2···N3iii | 0.86 | 2.54 | 3.055 (2) | 120 |
| Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x, −y+2, −z+2; (iii) x−1/2, −y+3/2, z+1/2. |
This work was supported by the Adult–Young Science Foundation of Guangxi Province (0447009), P. R. China.
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The title compound was obtained by the reaction of methyl 1H-1,2,4-triazole-3-carboxylate and ammonium hydroxide. The C=O bond length of 1.2524 (18) Å suggests that the title compound is in the amide form. N—H···O and N—H···N hydrogen bonds link molecules into infinite sheets. These sheets provide the two-dimensional network in and paralell to the {101} plane of the cell.