Acta Cryst. (2008). E64, o2085 [ doi:10.1107/S1600536808030584 ]
The title compound, C11H10N4O4·H2O, was synthesized from 1-azidomethyl-3-nitrobenzene and ethyl acetylacetate. Single-crystal X-ray analysis reveals that the dihedral angle between the triazole and benzene ring planes is 84.80 (2)°. The packing of the molecules is stabilized by strong O-H
O hydrogen bonds involving the solvent water molecules as donors and acceptors. The resulting layers are arranged into a three-dimensional framework via weak C-HO interactions.
The title compound was prepared from 1-(azidomethyl)-3-nitrobenzene, according to the reported method (EI Khadem et al., 1968), in 70% yield. Colourless prisms of (I) were obtained by slow evaporation of a 95% ethanol/water solution at room temperature.
All H atoms were detected in a difference map. Nevertheless, all C-bonded H atoms were placed in calculated positions, and constrained in a riding motion approximation with fixed bond lengths and Uiso parameters: Caryl—H = 0.93 Å, with Uiso(H) = 1.2Ueq(C); Cmethyl—H = 0.96 Å, with Uiso(H) = 1.5Ueq(C); Cmethylene—H = 0.97 Å, with Uiso(H) = 1.2Ueq(C); O—H bonds for the water molecule were constrained to 0.94 Å and 0.85 Å, with Uiso(H) = 1.5Ueq(O1W). Finally, the hydroxyl H atom (H2) was refined freely.
Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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]](./bh2192fig1thm.gif)
| Fig. 1. The molecular structure of (I), showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. |
![[Figure 2]](./bh2192fig2thm.gif)
| Fig. 2. Packing diagram of the title compound, showing the crystal structure along the b axis. |
| C11H10N4O4·H2O | Z = 2 |
| Mr = 280.25 | F(000) = 292 |
| Triclinic, P1 | Dx = 1.442 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 7.1649 (14) Å | Cell parameters from 5670 reflections |
| b = 8.2064 (16) Å | θ = 3.1–27.5° |
| c = 11.281 (2) Å | µ = 0.12 mm−1 |
| α = 84.88 (3)° | T = 293 K |
| β = 77.70 (2)° | Prism, colourless |
| γ = 89.38 (3)° | 0.20 × 0.18 × 0.15 mm |
| V = 645.5 (2) Å3 |
| Rigaku SCXmini diffractometer | 2959 independent reflections |
| Radiation source: fine-focus sealed tube | 1824 reflections with I > 2σ(I) |
| graphite | Rint = 0.040 |
| Detector resolution: 13.6612 pixels mm-1 | θmax = 27.5°, θmin = 3.1° |
| ω scans | h = −9→9 |
| Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) | k = −10→10 |
| Tmin = 0.965, Tmax = 0.977 | l = −14→14 |
| 6749 measured reflections |
| 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)] = 0.064 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.181 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.02 | w = 1/[σ2(Fo2) + (0.0847P)2 + 0.0594P] where P = (Fo2 + 2Fc2)/3 |
| 2959 reflections | (Δ/σ)max < 0.001 |
| 186 parameters | Δρmax = 0.27 e Å−3 |
| 3 restraints | Δρmin = −0.21 e Å−3 |
| 0 constraints |
| C11H10N4O4·H2O | γ = 89.38 (3)° |
| Mr = 280.25 | V = 645.5 (2) Å3 |
| Triclinic, P1 | Z = 2 |
| a = 7.1649 (14) Å | Mo Kα radiation |
| b = 8.2064 (16) Å | µ = 0.12 mm−1 |
| c = 11.281 (2) Å | T = 293 K |
| α = 84.88 (3)° | 0.20 × 0.18 × 0.15 mm |
| β = 77.70 (2)° |
| Rigaku SCXmini diffractometer | 2959 independent reflections |
| Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) | 1824 reflections with I > 2σ(I) |
| Tmin = 0.965, Tmax = 0.977 | Rint = 0.040 |
| 6749 measured reflections | θmax = 27.5° |
| R[F2 > 2σ(F2)] = 0.064 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.181 | Δρmax = 0.27 e Å−3 |
| S = 1.02 | Δρmin = −0.21 e Å−3 |
| 2959 reflections | Absolute structure: ? |
| 186 parameters | Flack parameter: ? |
| 3 restraints | Rogers parameter: ? |
| x | y | z | Uiso*/Ueq | ||
| C1 | 0.7354 (3) | −0.2576 (3) | 0.1023 (2) | 0.0489 (6) | |
| C2 | 0.8477 (3) | −0.1276 (3) | 0.13603 (19) | 0.0445 (5) | |
| C3 | 0.7947 (3) | 0.0281 (3) | 0.16613 (19) | 0.0453 (5) | |
| C4 | 0.6141 (4) | 0.1200 (3) | 0.1754 (3) | 0.0662 (7) | |
| H4A | 0.5476 | 0.1149 | 0.2591 | 0.099* | |
| H4B | 0.5357 | 0.0725 | 0.1281 | 0.099* | |
| H4C | 0.6419 | 0.2321 | 0.1451 | 0.099* | |
| C5 | 0.9906 (4) | 0.2546 (3) | 0.2222 (2) | 0.0552 (6) | |
| H5A | 0.9527 | 0.3352 | 0.1637 | 0.066* | |
| H5B | 1.1266 | 0.2683 | 0.2166 | 0.066* | |
| C6 | 0.8858 (3) | 0.2880 (3) | 0.3486 (2) | 0.0481 (6) | |
| C7 | 0.8471 (3) | 0.4501 (3) | 0.3709 (2) | 0.0490 (6) | |
| H7 | 0.8787 | 0.5334 | 0.3083 | 0.059* | |
| C8 | 0.7616 (3) | 0.4858 (3) | 0.4866 (2) | 0.0525 (6) | |
| C9 | 0.7117 (4) | 0.3678 (4) | 0.5813 (2) | 0.0673 (7) | |
| H9 | 0.6549 | 0.3952 | 0.6589 | 0.081* | |
| C10 | 0.7481 (5) | 0.2061 (4) | 0.5582 (2) | 0.0755 (8) | |
| H10 | 0.7139 | 0.1233 | 0.6209 | 0.091* | |
| C11 | 0.8352 (4) | 0.1670 (3) | 0.4426 (2) | 0.0634 (7) | |
| H11 | 0.8597 | 0.0582 | 0.4282 | 0.076* | |
| N1 | 1.0337 (3) | −0.1508 (2) | 0.14233 (18) | 0.0543 (5) | |
| N2 | 1.0999 (3) | −0.0190 (2) | 0.17513 (19) | 0.0584 (6) | |
| N3 | 0.9557 (3) | 0.0908 (2) | 0.18882 (17) | 0.0487 (5) | |
| N4 | 0.7247 (3) | 0.6596 (3) | 0.5081 (3) | 0.0710 (7) | |
| O1 | 0.8110 (3) | −0.3876 (2) | 0.07308 (19) | 0.0758 (6) | |
| O2 | 0.5593 (3) | −0.2220 (3) | 0.1079 (2) | 0.0867 (7) | |
| H2 | 0.506 (8) | −0.295 (6) | 0.091 (5) | 0.18 (2)* | |
| O3 | 0.7575 (4) | 0.7611 (3) | 0.4204 (3) | 0.1067 (9) | |
| O4 | 0.6635 (3) | 0.6915 (3) | 0.6118 (2) | 0.1040 (8) | |
| O1W | 0.2862 (2) | 0.5822 (2) | 0.09151 (18) | 0.0707 (6) | |
| H1A | 0.2667 | 0.5412 | 0.0287 | 0.106* | |
| H1B | 0.1813 | 0.6510 | 0.1111 | 0.106* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.0516 (14) | 0.0470 (13) | 0.0509 (14) | −0.0009 (11) | −0.0142 (10) | −0.0120 (10) |
| C2 | 0.0458 (13) | 0.0474 (12) | 0.0410 (12) | 0.0008 (10) | −0.0070 (9) | −0.0130 (9) |
| C3 | 0.0468 (13) | 0.0465 (12) | 0.0426 (12) | −0.0009 (10) | −0.0066 (9) | −0.0113 (9) |
| C4 | 0.0578 (16) | 0.0592 (16) | 0.085 (2) | 0.0136 (13) | −0.0185 (13) | −0.0156 (14) |
| C5 | 0.0648 (16) | 0.0449 (13) | 0.0547 (14) | −0.0102 (11) | −0.0053 (11) | −0.0150 (11) |
| C6 | 0.0523 (14) | 0.0444 (13) | 0.0492 (13) | −0.0073 (10) | −0.0112 (10) | −0.0122 (10) |
| C7 | 0.0528 (14) | 0.0455 (13) | 0.0500 (13) | −0.0056 (11) | −0.0120 (10) | −0.0087 (10) |
| C8 | 0.0467 (13) | 0.0567 (14) | 0.0573 (15) | −0.0022 (11) | −0.0113 (11) | −0.0218 (12) |
| C9 | 0.0653 (17) | 0.086 (2) | 0.0511 (15) | −0.0053 (15) | −0.0088 (12) | −0.0182 (14) |
| C10 | 0.093 (2) | 0.077 (2) | 0.0520 (17) | −0.0084 (17) | −0.0088 (14) | 0.0071 (14) |
| C11 | 0.0809 (19) | 0.0481 (14) | 0.0610 (17) | −0.0022 (13) | −0.0148 (13) | −0.0049 (12) |
| N1 | 0.0478 (12) | 0.0561 (12) | 0.0629 (13) | 0.0029 (9) | −0.0125 (9) | −0.0257 (10) |
| N2 | 0.0509 (12) | 0.0593 (13) | 0.0689 (14) | 0.0023 (10) | −0.0136 (10) | −0.0255 (11) |
| N3 | 0.0495 (11) | 0.0448 (11) | 0.0521 (11) | −0.0024 (9) | −0.0068 (8) | −0.0163 (9) |
| N4 | 0.0608 (14) | 0.0758 (17) | 0.0824 (18) | 0.0047 (12) | −0.0141 (12) | −0.0429 (15) |
| O1 | 0.0991 (15) | 0.0526 (11) | 0.0874 (14) | 0.0051 (10) | −0.0357 (11) | −0.0311 (10) |
| O2 | 0.0653 (14) | 0.0731 (14) | 0.132 (2) | −0.0111 (11) | −0.0395 (13) | −0.0188 (13) |
| O3 | 0.144 (2) | 0.0529 (13) | 0.115 (2) | −0.0030 (14) | −0.0029 (17) | −0.0215 (13) |
| O4 | 0.1111 (19) | 0.1131 (19) | 0.0943 (17) | 0.0254 (15) | −0.0156 (14) | −0.0625 (15) |
| O1W | 0.0632 (12) | 0.0561 (11) | 0.0935 (14) | −0.0015 (9) | −0.0099 (10) | −0.0259 (10) |
| C1—O1 | 1.230 (3) | C7—C8 | 1.374 (3) |
| C1—O2 | 1.282 (3) | C7—H7 | 0.9300 |
| C1—C2 | 1.467 (3) | C8—C9 | 1.366 (4) |
| C2—N1 | 1.360 (3) | C8—N4 | 1.479 (3) |
| C2—C3 | 1.380 (3) | C9—C10 | 1.386 (4) |
| C3—N3 | 1.350 (3) | C9—H9 | 0.9300 |
| C3—C4 | 1.479 (3) | C10—C11 | 1.385 (4) |
| C4—H4A | 0.9600 | C10—H10 | 0.9300 |
| C4—H4B | 0.9600 | C11—H11 | 0.9300 |
| C4—H4C | 0.9600 | N1—N2 | 1.300 (3) |
| C5—N3 | 1.466 (3) | N2—N3 | 1.356 (3) |
| C5—C6 | 1.510 (3) | N4—O4 | 1.210 (3) |
| C5—H5A | 0.9700 | N4—O3 | 1.219 (3) |
| C5—H5B | 0.9700 | O2—H2 | 0.77 (5) |
| C6—C11 | 1.377 (3) | O1W—H1B | 0.9349 |
| C6—C7 | 1.391 (3) | O1W—H1A | 0.8483 |
| O1—C1—O2 | 125.6 (2) | C8—C7—H7 | 120.4 |
| O1—C1—C2 | 120.3 (2) | C6—C7—H7 | 120.4 |
| O2—C1—C2 | 114.1 (2) | C9—C8—C7 | 122.6 (2) |
| N1—C2—C3 | 109.06 (19) | C9—C8—N4 | 119.4 (2) |
| N1—C2—C1 | 121.1 (2) | C7—C8—N4 | 118.0 (2) |
| C3—C2—C1 | 129.8 (2) | C8—C9—C10 | 118.1 (2) |
| N3—C3—C2 | 103.26 (19) | C8—C9—H9 | 121.0 |
| N3—C3—C4 | 123.4 (2) | C10—C9—H9 | 121.0 |
| C2—C3—C4 | 133.4 (2) | C11—C10—C9 | 120.4 (2) |
| C3—C4—H4A | 109.5 | C11—C10—H10 | 119.8 |
| C3—C4—H4B | 109.5 | C9—C10—H10 | 119.8 |
| H4A—C4—H4B | 109.5 | C6—C11—C10 | 120.6 (2) |
| C3—C4—H4C | 109.5 | C6—C11—H11 | 119.7 |
| H4A—C4—H4C | 109.5 | C10—C11—H11 | 119.7 |
| H4B—C4—H4C | 109.5 | N2—N1—C2 | 109.17 (19) |
| N3—C5—C6 | 114.05 (19) | N1—N2—N3 | 106.90 (18) |
| N3—C5—H5A | 108.7 | C3—N3—N2 | 111.60 (18) |
| C6—C5—H5A | 108.7 | C3—N3—C5 | 129.1 (2) |
| N3—C5—H5B | 108.7 | N2—N3—C5 | 119.26 (18) |
| C6—C5—H5B | 108.7 | O4—N4—O3 | 124.3 (3) |
| H5A—C5—H5B | 107.6 | O4—N4—C8 | 117.7 (3) |
| C11—C6—C7 | 119.2 (2) | O3—N4—C8 | 118.0 (2) |
| C11—C6—C5 | 123.2 (2) | C1—O2—H2 | 110 (4) |
| C7—C6—C5 | 117.5 (2) | H1B—O1W—H1A | 102.8 |
| C8—C7—C6 | 119.1 (2) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C4—H4A···O4i | 0.96 | 2.52 | 3.267 (3) | 135 |
| O1W—H1A···O1ii | 0.85 | 1.94 | 2.755 (3) | 161 |
| O1W—H1B···N1iii | 0.93 | 1.95 | 2.846 (3) | 160 |
| C11—H11···O3iv | 0.93 | 2.57 | 3.423 (4) | 153 |
| O2—H2···O1Wiv | 0.77 (5) | 1.88 (5) | 2.592 (3) | 153 (6) |
| Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y, −z; (iii) x−1, y+1, z; (iv) x, y−1, z. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C4—H4A···O4i | 0.96 | 2.52 | 3.267 (3) | 135 |
| O1W—H1A···O1ii | 0.85 | 1.94 | 2.755 (3) | 161 |
| O1W—H1B···N1iii | 0.93 | 1.95 | 2.846 (3) | 160 |
| C11—H11···O3iv | 0.93 | 2.57 | 3.423 (4) | 153 |
| O2—H2···O1Wiv | 0.77 (5) | 1.88 (5) | 2.592 (3) | 153 (6) |
| Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y, −z; (iii) x−1, y+1, z; (iv) x, y−1, z. |
EI Khadem, H., Mansour, H. A. R. & Meshriki, M. H. (1968). J. Chem. Soc. C, pp. 1329–1331. EI or El Khadem?
Olesen, P. H., Sørensen, A. R., Urso, B., Kurtzhals, P., Bowler, A. N., Ehrbar, U. & Hansen, B. F. (2003). J. Med. Chem. 46, 3333–3341.
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Tian, L., Sun, Y., Li, H., Zheng, X., Cheng, Y., Liu, X. & Qian, B. (2005). J. Inorg. Biochem. 99, 1646–1652.
It is well known that many triazole-related molecules have received much attention due to their biological activities (Olesen et al., 2003; Tian et al., 2005). We report herein the crystal structure of the title compound, (I, Fig. 1). The bond lengths and angles have normal values. The dihedral angle between the triazole and phenyl planes is 84.80 (2)°. The packing of the molecules is stabilized by strong hydrogen bonds (Table 1) between the triazole molecules and lattice water molecules. Meanwhile, the 0D discrete molecules are arranged into a three-dimensional framework via hydrogen bond interactions and weak contacts (Fig. 2).