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access2-(4H-1,2,4-Triazol-4-yl)phenol
aDepartment of Physics, Huainan Normal University, Huainan, Anhui 232001, People's Republic of China, bDepartment of Chemistry & Chemical Engineering, Huainan Normal University, Huainan, Anhui 232001, People's Republic of China, and cCollege of Chemical Engineering, Weifang University, Weifang, Shandong 261061, People's Republic of China
*Correspondence e-mail: zwwwz@live.com
In the title compound, C8H7N3O, the dihedral angle between the benzene and triazole rings is 41.74 (12)°.
Related literature
For the use of substituted 1,2,4-triazoles as ligands, see: Ouellette et al. (2006![[Ouellette, W., Yu, M. H., O' Connor, C. J., Hagrman, D. & Zubieta, J. (2006). Angew. Chem. Int. Ed. 45, 3497-3500.]](../../../../../../logos/arrows/e_arr.gif "Ouellette, W., Yu, M. H., O' Connor, C. J., Hagrman, D. & Zubieta, J. (2006). Angew. Chem. Int. Ed. 45, 3497-3500.")
); Zhang et al. (2005); Zhou et al. (2007, 2008). For related structures, see: Wiley & Hart (1953); Bartlett & Humphrey (1967); Li et al. (2004); Zhu et al. (2000); Xu et al. (2004).
![[Scheme 1]](jh2195scheme1.gif)
Experimental
Crystal data
|
Data collection: CrystalClear (Rigaku, 2002); cell CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Supporting information
contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810031739/jh2195sup1.cif
Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810031739/jh2195Isup2.hkl
The title compound was prepared by reacting diformylhydrazine (0.6 mmol, 0.053 g) and o-aminophenol (0.6 mmol, 0.065 g) in a Telon-lined stainless steel autoclave in a furnace at 443 K for 2 d. The reaction vessel was then cooled to 293 K. The product was isolated and washed with hot water and hot ethanol and black crystals suitable for X-ray diffraction studies were obtained. The crystals are air-stable. Yield based on o-aminophenol: 0.062 g, 64%. Elemental analysis (%) for C8H7N3O, found (calculated): C 59.70 (59.61), H 4.25 (4.38), N 26.06 (26.08).
Hydrogen atoms were allowed to ride on their respective parent atoms with C—H distances of 0.93 Å, and were included in the with isotropic displacement parameters Uiso(H) = 1.2Ueq(C).
Many compounds with uncommon properties have been widely investigated by using substituted 1,2,4-triazoles ligands, resulting from their rich coordination fashions and broad potential applications in various fields (Ouellette et al. (2006); Zhang et al. (2005); Zhou et al. (2007); Zhou et al. (2008)). Substituted 1,2,4-triazoles can be synthesized from different and diformylhydrazine. The triazole ring, having strong -donor and weak-acceptor properties, potentially has two different coordination modes through three nitrogen-donor atoms coordinating to metal ions. Recently, we have prepared some new substituted 1,2,4-triazole derivatives and their transition-metal complexes, and we report here the analysis of 2-(1H-1,2,4-Triazol-4-yl)phenol, (I).
For the use of substituted 1,2,4-triazoles as ligands, see: Ouellette et al. (2006); Zhang et al. (2005); Zhou et al. (2007, 2008). For related structures, see: Wiley et al. (1953); Bartlett et al. (1967); Li et al. (2004); Zhu et al. (2000); Xu et al. (2004).
Data collection: CrystalClear (Rigaku, 2002); cell CrystalClear (Rigaku, 2002); data reduction: CrystalClear (Rigaku, 2002); 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]](./jh2195fig1thm.gif) | Fig. 1. The structure of (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme. |
![[Figure 2]](./jh2195fig2thm.gif) | Fig. 2. View of the 3-D structure of the title compound. |
| C8H7N3O | F(000) = 336 |
| Mr = 161.17 | Dx = 1.337 Mg m−3 |
| Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
| a = 7.273 (3) Å | Cell parameters from 1048 reflections |
| b = 14.265 (4) Å | θ = 2.6–27.4° |
| c = 7.720 (3) Å | µ = 0.09 mm−1 |
| β = 90.93 (3)° | T = 293 K |
| V = 800.8 (5) Å3 | Block, black |
| Z = 4 | 0.42 × 0.37 × 0.35 mm |
| Rigaku Mercury CCD diffractometer | 1460 independent reflections |
| Radiation source: rotating-anode generator | 863 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.057 |
| ω scans | θmax = 25.4°, θmin = 3.0° |
| Absorption correction: multi-scan (Sphere in CrystalClear; Rigaku, 2002) | h = −8→8 |
| Tmin = 0.815, Tmax = 1.000 | k = −16→17 |
| 5037 measured reflections | l = −9→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)] = 0.067 | H-atom parameters constrained |
| wR(F2) = 0.237 | w = 1/[σ2(Fo2) + (0.144P)2] where P = (Fo2 + 2Fc2)/3 |
| S = 1.09 | (Δ/σ)max < 0.001 |
| 1460 reflections | Δρmax = 0.44 e Å−3 |
| 110 parameters | Δρmin = −0.44 e Å−3 |
| 0 restraints | Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.08 (3) |
| C8H7N3O | V = 800.8 (5) Å3 |
| Mr = 161.17 | Z = 4 |
| Monoclinic, P21/n | Mo Kα radiation |
| a = 7.273 (3) Å | µ = 0.09 mm−1 |
| b = 14.265 (4) Å | T = 293 K |
| c = 7.720 (3) Å | 0.42 × 0.37 × 0.35 mm |
| β = 90.93 (3)° |
| Rigaku Mercury CCD diffractometer | 1460 independent reflections |
| Absorption correction: multi-scan (Sphere in CrystalClear; Rigaku, 2002) | 863 reflections with I > 2σ(I) |
| Tmin = 0.815, Tmax = 1.000 | Rint = 0.057 |
| 5037 measured reflections |
| R[F2 > 2σ(F2)] = 0.067 | 0 restraints |
| wR(F2) = 0.237 | H-atom parameters constrained |
| S = 1.09 | Δρmax = 0.44 e Å−3 |
| 1460 reflections | Δρmin = −0.44 e Å−3 |
| 110 parameters |
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 | 0.5881 (5) | 0.7175 (2) | 0.7593 (5) | 0.0559 (10) | |
| H1A | 0.5053 | 0.7418 | 0.8381 | 0.067* | |
| C2 | 0.7294 (5) | 0.6248 (2) | 0.5912 (4) | 0.0510 (10) | |
| H2A | 0.7633 | 0.5718 | 0.5293 | 0.061* | |
| C3 | 0.4535 (4) | 0.5571 (2) | 0.7425 (4) | 0.0423 (8) | |
| C4 | 0.5137 (4) | 0.4665 (2) | 0.7748 (4) | 0.0448 (9) | |
| C5 | 0.3858 (5) | 0.4004 (2) | 0.8286 (4) | 0.0542 (10) | |
| H5A | 0.4233 | 0.3394 | 0.8527 | 0.065* | |
| C6 | 0.2034 (5) | 0.4252 (3) | 0.8463 (5) | 0.0651 (11) | |
| H6A | 0.1194 | 0.3807 | 0.8837 | 0.078* | |
| C7 | 0.1443 (5) | 0.5148 (3) | 0.8091 (5) | 0.0633 (11) | |
| H7A | 0.0210 | 0.5308 | 0.8200 | 0.076* | |
| C8 | 0.2698 (5) | 0.5804 (3) | 0.7557 (5) | 0.0582 (10) | |
| H8A | 0.2309 | 0.6408 | 0.7284 | 0.070* | |
| N1 | 0.7219 (4) | 0.76432 (19) | 0.6942 (4) | 0.0632 (10) | |
| N2 | 0.8157 (4) | 0.70426 (19) | 0.5852 (4) | 0.0618 (10) | |
| N3 | 0.5836 (3) | 0.62837 (17) | 0.6985 (3) | 0.0443 (8) | |
| O1 | 0.6918 (3) | 0.44556 (15) | 0.7550 (3) | 0.0582 (8) | |
| H1B | 0.7472 | 0.4923 | 0.7229 | 0.087* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.068 (2) | 0.0332 (18) | 0.068 (2) | 0.0041 (15) | 0.0238 (18) | 0.0022 (16) |
| C2 | 0.057 (2) | 0.0414 (18) | 0.0553 (19) | −0.0010 (15) | 0.0129 (17) | 0.0025 (15) |
| C3 | 0.0378 (18) | 0.0426 (17) | 0.0466 (17) | −0.0030 (14) | 0.0046 (13) | 0.0028 (14) |
| C4 | 0.0428 (19) | 0.0414 (19) | 0.0504 (17) | −0.0018 (14) | 0.0042 (14) | 0.0001 (14) |
| C5 | 0.060 (2) | 0.0429 (19) | 0.060 (2) | −0.0089 (15) | 0.0074 (18) | 0.0071 (16) |
| C6 | 0.058 (2) | 0.075 (3) | 0.063 (2) | −0.024 (2) | 0.0154 (18) | −0.005 (2) |
| C7 | 0.047 (2) | 0.070 (3) | 0.072 (2) | −0.0036 (18) | 0.0121 (18) | −0.001 (2) |
| C8 | 0.050 (2) | 0.058 (2) | 0.067 (2) | 0.0034 (16) | 0.0065 (17) | 0.0065 (17) |
| N1 | 0.073 (2) | 0.0368 (16) | 0.081 (2) | −0.0025 (14) | 0.0284 (17) | −0.0018 (15) |
| N2 | 0.065 (2) | 0.0458 (17) | 0.076 (2) | −0.0100 (14) | 0.0222 (16) | −0.0004 (14) |
| N3 | 0.0449 (16) | 0.0329 (15) | 0.0553 (16) | 0.0000 (11) | 0.0117 (12) | 0.0012 (11) |
| O1 | 0.0451 (15) | 0.0400 (13) | 0.0897 (19) | 0.0004 (10) | 0.0081 (12) | 0.0087 (12) |
| C1—N1 | 1.289 (4) | C4—C5 | 1.393 (4) |
| C1—N3 | 1.356 (4) | C5—C6 | 1.382 (5) |
| C1—H1A | 0.9300 | C5—H5A | 0.9300 |
| C2—N2 | 1.297 (4) | C6—C7 | 1.378 (6) |
| C2—N3 | 1.357 (4) | C6—H6A | 0.9300 |
| C2—H2A | 0.9300 | C7—C8 | 1.375 (5) |
| C3—C8 | 1.382 (4) | C7—H7A | 0.9300 |
| C3—C4 | 1.385 (5) | C8—H8A | 0.9300 |
| C3—N3 | 1.433 (4) | N1—N2 | 1.388 (4) |
| C4—O1 | 1.340 (4) | O1—H1B | 0.8200 |
| N1—C1—N3 | 111.4 (3) | C7—C6—C5 | 120.9 (3) |
| N1—C1—H1A | 124.3 | C7—C6—H6A | 119.5 |
| N3—C1—H1A | 124.3 | C5—C6—H6A | 119.5 |
| N2—C2—N3 | 111.9 (3) | C8—C7—C6 | 119.2 (3) |
| N2—C2—H2A | 124.1 | C8—C7—H7A | 120.4 |
| N3—C2—H2A | 124.1 | C6—C7—H7A | 120.4 |
| C8—C3—C4 | 120.9 (3) | C7—C8—C3 | 120.4 (4) |
| C8—C3—N3 | 119.3 (3) | C7—C8—H8A | 119.8 |
| C4—C3—N3 | 119.8 (3) | C3—C8—H8A | 119.8 |
| O1—C4—C3 | 119.4 (3) | C1—N1—N2 | 107.4 (3) |
| O1—C4—C5 | 122.3 (3) | C2—N2—N1 | 105.9 (3) |
| C3—C4—C5 | 118.4 (3) | C1—N3—C2 | 103.4 (2) |
| C6—C5—C4 | 120.2 (3) | C1—N3—C3 | 126.6 (3) |
| C6—C5—H5A | 119.9 | C2—N3—C3 | 130.0 (3) |
| C4—C5—H5A | 119.9 | C4—O1—H1B | 109.5 |
Experimental details
| Crystal data | |
| Chemical formula | C8H7N3O |
| Mr | 161.17 |
| Crystal system, space group | Monoclinic, P21/n |
| Temperature (K) | 293 |
| a, b, c (Å) | 7.273 (3), 14.265 (4), 7.720 (3) |
| β (°) | 90.93 (3) |
| V (Å3) | 800.8 (5) |
| Z | 4 |
| Radiation type | Mo Kα |
| µ (mm−1) | 0.09 |
| Crystal size (mm) | 0.42 × 0.37 × 0.35 |
| Data collection | |
| Diffractometer | Rigaku Mercury CCD |
| Absorption correction | Multi-scan (Sphere in CrystalClear; Rigaku, 2002) |
| Tmin, Tmax | 0.815, 1.000 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 5037, 1460, 863 |
| Rint | 0.057 |
| (sin θ/λ)max (Å−1) | 0.602 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.067, 0.237, 1.09 |
| No. of reflections | 1460 |
| No. of parameters | 110 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.44, −0.44 |
Computer programs: CrystalClear (Rigaku, 2002), SHELXTL (Sheldrick, 2008).
Acknowledgements
We gratefully acknowledge financial support from the Natural Science Foundation of the Education Department of Anhui Province (KJ2010B203, KJ2010B205) and the Science Foundation of Shandong Province (ZR2009BM041).
References
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| CRYSTALLOGRAPHIC COMMUNICATIONS |
Many compounds with uncommon properties have been widely investigated by using substituted 1,2,4-triazoles ligands, resulting from their rich coordination fashions and broad potential applications in various fields (Ouellette et al. (2006); Zhang et al. (2005); Zhou et al. (2007); Zhou et al. (2008)). Substituted 1,2,4-triazoles can be synthesized from different amines and diformylhydrazine. The triazole ring, having strong -donor and weak-acceptor properties, potentially has two different coordination modes through three nitrogen-donor atoms coordinating to metal ions. Recently, we have prepared some new substituted 1,2,4-triazole derivatives and their transition-metal complexes, and we report here the crystal structure analysis of 2-(1H-1,2,4-Triazol-4-yl)phenol, (I).