Acta Cryst. (2009). E65, o1258 [ doi:10.1107/S160053680901678X ]
In the title compound, C11H11N3O2·H2O, the planes of the triazole and phenyl rings are almost perpendicular to each other [dihedral angle 89.5 (3)°]. The crystal packing is stabilized by strong intermolecular O-H
O and O-HN hydrogen bonds involving the water molecule as both donor and acceptor.
The title compound was prepared from azidomethylbenzene according to the reported method (El Khadem et al., 1968). Colourless prismatic crystals suitable for X-ray analysis were obtained by slow evaporation of a 95% ethanol/water solution at room temperature.
The water and carboxylic H atoms were located from a difference Fourier map but not refined [Uiso(H) = 1.5Ueq(O)]. All other H atoms were fixed geometrically and treated as riding, with C—H = 0.93-0.97 Å and with Uiso(H) = 1.2Ueq(C) or 1.5 Ueq(C) for methyl H atoms.
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]](./rz2316fig1thm.gif)
| Fig. 1. The molecular structure of the title compound, showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. |
![[Figure 2]](./rz2316fig2thm.gif)
| Fig. 2. Packing diagram of the title compound viewed along the b axis. Intermolecular H bonds are shown as dashed lines. |
| C11H11N3O2·H2O | Z = 2 |
| Mr = 235.24 | F000 = 248 |
| Triclinic, P1 | Dx = 1.306 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation λ = 0.71073 Å |
| a = 6.5808 (13) Å | Cell parameters from 1986 reflections |
| b = 7.4995 (15) Å | θ = 2.6–27.5º |
| c = 12.337 (3) Å | µ = 0.10 mm−1 |
| α = 99.87 (4)º | T = 292 K |
| β = 93.75 (3)º | Prism, colourless |
| γ = 91.80 (3)º | 0.35 × 0.30 × 0.25 mm |
| V = 598.0 (2) Å3 |
| Rigaku SCXmini diffractometer | 2730 independent reflections |
| Radiation source: fine-focus sealed tube | 1540 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.042 |
| Detector resolution: 13.6612 pixels mm-1 | θmax = 27.5º |
| T = 292 K | θmin = 3.1º |
| ω scans | h = −8→8 |
| Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) | k = −9→9 |
| Tmin = 0.963, Tmax = 0.976 | l = −15→15 |
| 6256 measured reflections |
| 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)] = 0.064 | H-atom parameters constrained |
| wR(F2) = 0.174 | w = 1/[σ2(Fo2) + (0.0599P)2 + 0.187P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.05 | (Δ/σ)max < 0.001 |
| 2730 reflections | Δρmax = 0.19 e Å−3 |
| 156 parameters | Δρmin = −0.15 e Å−3 |
| Primary atom site location: structure-invariant direct methods | Extinction correction: none |
| C11H11N3O2·H2O | γ = 91.80 (3)º |
| Mr = 235.24 | V = 598.0 (2) Å3 |
| Triclinic, P1 | Z = 2 |
| a = 6.5808 (13) Å | Mo Kα |
| b = 7.4995 (15) Å | µ = 0.10 mm−1 |
| c = 12.337 (3) Å | T = 292 K |
| α = 99.87 (4)º | 0.35 × 0.30 × 0.25 mm |
| β = 93.75 (3)º |
| Rigaku SCXmini diffractometer | 2730 independent reflections |
| Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) | 1540 reflections with I > 2σ(I) |
| Tmin = 0.963, Tmax = 0.976 | Rint = 0.042 |
| 6256 measured reflections |
| R[F2 > 2σ(F2)] = 0.064 | 156 parameters |
| wR(F2) = 0.174 | H-atom parameters constrained |
| S = 1.05 | Δρmax = 0.19 e Å−3 |
| 2730 reflections | Δρmin = −0.15 e Å−3 |
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 | ||
| C1 | 0.2853 (4) | 0.2569 (4) | 0.9216 (2) | 0.0526 (6) | |
| C2 | 0.4367 (4) | 0.3462 (3) | 0.86392 (19) | 0.0484 (6) | |
| C3 | 0.6073 (4) | 0.2769 (3) | 0.8171 (2) | 0.0531 (6) | |
| C4 | 0.6958 (5) | 0.0956 (4) | 0.8063 (3) | 0.0767 (9) | |
| H4A | 0.6878 | 0.0398 | 0.7300 | 0.115* | |
| H4B | 0.6210 | 0.0212 | 0.8473 | 0.115* | |
| H4C | 0.8359 | 0.1084 | 0.8346 | 0.115* | |
| C5 | 0.8767 (4) | 0.4291 (5) | 0.7208 (2) | 0.0715 (8) | |
| H5A | 0.9851 | 0.3738 | 0.7586 | 0.086* | |
| H5B | 0.9167 | 0.5557 | 0.7242 | 0.086* | |
| C6 | 0.8532 (4) | 0.3374 (4) | 0.6016 (2) | 0.0609 (7) | |
| C7 | 0.6735 (6) | 0.3212 (6) | 0.5403 (3) | 0.0988 (12) | |
| H7 | 0.5557 | 0.3604 | 0.5729 | 0.119* | |
| C8 | 0.6638 (8) | 0.2462 (7) | 0.4289 (3) | 0.1207 (15) | |
| H8 | 0.5399 | 0.2379 | 0.3872 | 0.145* | |
| C9 | 0.8314 (11) | 0.1859 (6) | 0.3814 (3) | 0.1187 (17) | |
| H9 | 0.8239 | 0.1327 | 0.3073 | 0.142* | |
| C10 | 1.0096 (9) | 0.2029 (6) | 0.4414 (5) | 0.1221 (16) | |
| H10 | 1.1271 | 0.1639 | 0.4083 | 0.146* | |
| C11 | 1.0215 (5) | 0.2769 (5) | 0.5510 (3) | 0.0872 (10) | |
| H11 | 1.1467 | 0.2860 | 0.5916 | 0.105* | |
| N1 | 0.4242 (3) | 0.5221 (3) | 0.85113 (17) | 0.0557 (6) | |
| N2 | 0.5786 (4) | 0.5666 (3) | 0.79918 (18) | 0.0624 (6) | |
| N3 | 0.6905 (3) | 0.4179 (3) | 0.77838 (16) | 0.0567 (6) | |
| O1 | 0.1510 (3) | 0.3660 (2) | 0.96493 (16) | 0.0649 (6) | |
| H1 | 0.0776 | 0.3125 | 1.0012 | 0.097* | |
| O2 | 0.2875 (4) | 0.0973 (3) | 0.9257 (2) | 0.0921 (8) | |
| O1W | 0.1065 (3) | 0.7618 (2) | 0.91803 (16) | 0.0709 (6) | |
| H1A | 0.2137 | 0.6876 | 0.9038 | 0.106* | |
| H1B | 0.1686 | 0.8670 | 0.9279 | 0.106* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.0594 (16) | 0.0472 (15) | 0.0502 (15) | −0.0021 (12) | 0.0062 (12) | 0.0056 (11) |
| C2 | 0.0559 (15) | 0.0463 (13) | 0.0418 (13) | −0.0018 (11) | 0.0051 (11) | 0.0043 (10) |
| C3 | 0.0562 (15) | 0.0564 (16) | 0.0425 (14) | −0.0037 (12) | 0.0033 (11) | −0.0016 (11) |
| C4 | 0.079 (2) | 0.0675 (19) | 0.079 (2) | 0.0093 (16) | 0.0153 (16) | −0.0065 (16) |
| C5 | 0.0516 (16) | 0.108 (2) | 0.0536 (17) | −0.0118 (15) | 0.0079 (13) | 0.0128 (16) |
| C6 | 0.0641 (18) | 0.0689 (18) | 0.0531 (16) | 0.0011 (14) | 0.0143 (14) | 0.0162 (13) |
| C7 | 0.080 (2) | 0.148 (4) | 0.059 (2) | 0.008 (2) | −0.0022 (18) | −0.007 (2) |
| C8 | 0.142 (4) | 0.149 (4) | 0.062 (2) | −0.002 (3) | −0.012 (3) | 0.003 (2) |
| C9 | 0.202 (6) | 0.096 (3) | 0.058 (2) | −0.009 (3) | 0.048 (3) | 0.003 (2) |
| C10 | 0.147 (4) | 0.114 (3) | 0.108 (4) | 0.016 (3) | 0.072 (3) | 0.001 (3) |
| C11 | 0.083 (2) | 0.092 (2) | 0.090 (3) | 0.0129 (19) | 0.0349 (19) | 0.013 (2) |
| N1 | 0.0634 (14) | 0.0531 (13) | 0.0527 (13) | −0.0007 (11) | 0.0119 (10) | 0.0125 (10) |
| N2 | 0.0677 (15) | 0.0653 (15) | 0.0570 (14) | −0.0054 (12) | 0.0119 (11) | 0.0172 (11) |
| N3 | 0.0560 (13) | 0.0677 (15) | 0.0446 (12) | −0.0065 (11) | 0.0065 (10) | 0.0052 (10) |
| O1 | 0.0683 (13) | 0.0601 (11) | 0.0732 (13) | 0.0066 (10) | 0.0273 (10) | 0.0220 (9) |
| O2 | 0.1035 (17) | 0.0458 (12) | 0.134 (2) | −0.0006 (11) | 0.0516 (15) | 0.0183 (12) |
| O1W | 0.0752 (13) | 0.0540 (11) | 0.0874 (14) | −0.0015 (10) | 0.0318 (11) | 0.0138 (10) |
| C1—O2 | 1.208 (3) | C6—C11 | 1.359 (4) |
| C1—O1 | 1.302 (3) | C7—C8 | 1.389 (5) |
| C1—C2 | 1.470 (3) | C7—H7 | 0.9300 |
| C2—N1 | 1.360 (3) | C8—C9 | 1.338 (6) |
| C2—C3 | 1.372 (3) | C8—H8 | 0.9300 |
| C3—N3 | 1.347 (3) | C9—C10 | 1.336 (6) |
| C3—C4 | 1.485 (4) | C9—H9 | 0.9300 |
| C4—H4A | 0.9600 | C10—C11 | 1.366 (6) |
| C4—H4B | 0.9600 | C10—H10 | 0.9300 |
| C4—H4C | 0.9600 | C11—H11 | 0.9300 |
| C5—N3 | 1.463 (3) | N1—N2 | 1.301 (3) |
| C5—C6 | 1.509 (4) | N2—N3 | 1.353 (3) |
| C5—H5A | 0.9700 | O1—H1 | 0.8200 |
| C5—H5B | 0.9700 | O1W—H1A | 0.9192 |
| C6—C7 | 1.352 (4) | O1W—H1B | 0.8630 |
| O2—C1—O1 | 124.7 (2) | C11—C6—C5 | 119.0 (3) |
| O2—C1—C2 | 122.0 (2) | C6—C7—C8 | 120.4 (4) |
| O1—C1—C2 | 113.3 (2) | C6—C7—H7 | 119.8 |
| N1—C2—C3 | 109.0 (2) | C8—C7—H7 | 119.8 |
| N1—C2—C1 | 122.0 (2) | C9—C8—C7 | 120.4 (4) |
| C3—C2—C1 | 129.0 (2) | C9—C8—H8 | 119.8 |
| N3—C3—C2 | 103.5 (2) | C7—C8—H8 | 119.8 |
| N3—C3—C4 | 123.9 (2) | C10—C9—C8 | 119.3 (4) |
| C2—C3—C4 | 132.6 (2) | C10—C9—H9 | 120.3 |
| C3—C4—H4A | 109.5 | C8—C9—H9 | 120.3 |
| C3—C4—H4B | 109.5 | C9—C10—C11 | 120.8 (4) |
| H4A—C4—H4B | 109.5 | C9—C10—H10 | 119.6 |
| C3—C4—H4C | 109.5 | C11—C10—H10 | 119.6 |
| H4A—C4—H4C | 109.5 | C6—C11—C10 | 121.0 (4) |
| H4B—C4—H4C | 109.5 | C6—C11—H11 | 119.5 |
| N3—C5—C6 | 113.3 (2) | C10—C11—H11 | 119.5 |
| N3—C5—H5A | 108.9 | N2—N1—C2 | 109.1 (2) |
| C6—C5—H5A | 108.9 | N1—N2—N3 | 106.8 (2) |
| N3—C5—H5B | 108.9 | C3—N3—N2 | 111.6 (2) |
| C6—C5—H5B | 108.9 | C3—N3—C5 | 129.6 (3) |
| H5A—C5—H5B | 107.7 | N2—N3—C5 | 118.8 (2) |
| C7—C6—C11 | 117.9 (3) | C1—O1—H1 | 109.5 |
| C7—C6—C5 | 123.0 (3) | H1A—O1W—H1B | 100.8 |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1W—H1A···N1 | 0.92 | 1.96 | 2.870 (3) | 172 |
| O1W—H1B···O2i | 0.86 | 1.88 | 2.734 (3) | 171 |
| O1—H1···O1Wii | 0.82 | 1.75 | 2.563 (3) | 168 |
| Symmetry codes: (i) x, y+1, z; (ii) −x, −y+1, −z+2. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1W—H1A···N1 | 0.92 | 1.96 | 2.870 (3) | 172 |
| O1W—H1B···O2i | 0.86 | 1.88 | 2.734 (3) | 171 |
| O1—H1···O1Wii | 0.82 | 1.75 | 2.563 (3) | 168 |
| Symmetry codes: (i) x, y+1, z; (ii) −x, −y+1, −z+2. |
This work was supported by funds provided by Southeast University for Young Researchera (4007041027). The author thanks Dr Z. R. Qu for her assistance with this work.
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Triazole-related molecules have attracted considerable attention due to their biological activities (Olesen et al., 2003; Tian et al., 2005). Recently, we have reported the cerystal structure of a few triazole compounds (Lin et al. 2008; Xiao et al.2008). As an extension of our work on the structural characterization of the triazole-related compounds, we report herein the crystal structure of the title compound.
In the molecule of the title compound (Fig. 1), bond lengths and angles have normal values. The dihedral angle between the triazole and phenyl rings is 89.5 (3)°. The packing is stabilized by strong intermolecular O—H···O and O—H···N hydrogen bonds involving the triazole molecules and lattice water molecules (Fig.2; Table 1).