2-[4-(2-Hy­droxy­propan-2-yl)-1H-1,2,3-triazol-1-yl]phenol

Li-Li Zhang; Kai Yu; Ling-Ling Liu; Dian-Shun Guo

doi:10.1107/S1600536812012925

. 2012 Mar 31;68(Pt 4):o1262. doi: 10.1107/S1600536812012925

2-[4-(2-Hydroxypropan-2-yl)-1H-1,2,3-triazol-1-yl]phenol

Li-Li Zhang ^a,^*, Kai Yu ^a, Ling-Ling Liu ^a, Dian-Shun Guo ^a

PMCID: PMC3344188 PMID: 22606191

Abstract

In the title compound, C₁₁H₁₃N₃O₂, the 1,2,3-triazole ring and the phenol ring form a dihedral angle of 55.46 (5)°. In the crystal, inversion-related molecules associate through pairs of hydroxy–phenol O—H⋯O hydrogen bonds, giving centrosymmetric cyclic dimers [graph set R ₂ ²(18)]. These dimers are linked into infinite chains along [001], giving an overall two-dimensional network structure parallel to the bc plane through hydroxy O—H⋯N and triazole C—H⋯N hydrogen bonds.

Related literature

For general background to 1,2,3-triazole derivatives, see: Shia et al. (2002 ▶); Orgueira et al. (2005 ▶); Crowley & Bandeen (2010 ▶). For related structures, see: Zou et al. (2006 ▶); Danielraj et al. (2010 ▶); Stöger et al. (2011 ▶). For bond-length data, see: Banerjee et al. (2002 ▶); Janas & Sobota (2005 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₁H₁₃N₃O₂
M _r = 219.24
Monoclinic,
a = 11.599 (2) Å
b = 9.0747 (18) Å
c = 10.743 (2) Å
β = 107.081 (3)°
V = 1080.9 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 K
0.40 × 0.30 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1999 ▶) T _min = 0.963, T _max = 0.983
5462 measured reflections
1994 independent reflections
1696 reflections with I > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.109
S = 1.05
1994 reflections
149 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: SMART (Bruker, 1999 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; 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.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812012925/zs2192sup1.cif

e-68-o1262-sup1.cif^{(16.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812012925/zs2192Isup2.hkl

e-68-o1262-Isup2.hkl^{(98.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812012925/zs2192Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1ⁱ	0.82	1.89	2.7090 (15)	173
O1—H1⋯N3ⁱⁱ	0.82	2.05	2.8665 (16)	171
C7—H7⋯N2ⁱⁱ	0.93	2.40	3.2738 (19)	157

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

Financial support from the National Natural Science Foundation of China (grant No. 20572064) and the Natural Science Foundation of Shandong Province (grant No. ZR2010BM022) is gratefully acknowledged.

supplementary crystallographic information

Comment

1,2,3-Triazole derivatives have received much attention owing to their wide applications in drug discovery, materials and supramolecular chemistry (Shia et al., 2002; Orgueira et al., 2005; Crowley & Bandeen 2010). Numerous crystal structures of triazole derivatives have been described (Danielraj et al., 2010; Stöger et al., 2011). We report here the structure of a new triazole compound, 2-[4-(2-hydroxypropan-2-yl)-1H-1,2,3-triazol-1-yl]phenol, C₁₁H₁₃N₃O₂.

The title compound, shown in Fig. 1, contains a 1,2,3-triazole ring and a phenol ring which are non-coplanar with a dihedral angle of 55.46 (5)°, larger than that reported previously for a similar structure [14.34 (17)°] (Zou et al., 2006). This difference may be ascribed to the steric repulsion between the heterocyclic N atom, N2, and the phenolic hydroxyl oxygen atom, O2. The bond lengths of C7—N1, C8—N3 and N1—N2 are shorter than the normal C—N single bond length (1.483 Å) (Banerjee et al., 2002) and N—N single bond length (1.467 Å) (Janas & Sobota, 2005), showing an obvious electron delocalization in the triazole ring.

The packing of the title compound is stabilized by intermolecular O—H···O, O—H···N and C—H···N hydrogen bonds (Table 1). Two inversion- related molecules form a centrosymmetric dimer through intermolecular hydroxyl O2—H···O1ⁱ hydrogen bonds, locally creating an R²₂(18) motif (Bernstein et al., 1995) (Fig. 2). These dimers are linked into chains which give an overall two-dimensional network structure through intermolecular hydroxyl O1—H···N3ⁱⁱ and triazole C7—H7···N2ⁱⁱ hydrogen-bonding interactions, which include a cyclic R²₂(8) motif (Fig. 3). For symmetry codes (i) and (ii), see Table 1.

Experimental

2-Methylbut-3-yn-2-ol (0.093 g, 1.1 mmol) was added to a suspension of 2-azidophenol (0.135 g, 1.0 mmol), CuI (0.019 g, 0.10 mmol), Et₃N (0.5 ml) and ascorbic acid (0.018 g, 0.10 mmol) in CH₃CN (2.0 ml) and continuously stirred at 298 K for 0.5 h. The resulting mixture was extracted with CH₂Cl₂ and the organic layer was washed with brine, then dried over anhydrous MgSO₄. After removal of the solvent under reduced pressure, the crude product was purified by recrystallization from CH₂Cl₂/pentane to afford the title compound as a pale yellow solid (95% yield). Single crystals of the title compound suitable for X-ray diffraction analysis were obtained by slow diffusion of pentane into a solution of the title compound in CH₂Cl₂ at 298 K.