2-(1H-Benzotriazol-1-yl)-3-(2,6-dichloro­phen­yl)-1-phenyl­propan-1-ol

Özden Özel Güven; Seval Çapanlar; Simon J Coles; Tuncer Hökelek

doi:10.1107/S1600536811034738

. 2011 Aug 27;67(Pt 9):o2510. doi: 10.1107/S1600536811034738

2-(1H-Benzotriazol-1-yl)-3-(2,6-dichlorophenyl)-1-phenylpropan-1-ol

Özden Özel Güven ^a, Seval Çapanlar ^a, Simon J Coles ^b, Tuncer Hökelek ^c,^*

PMCID: PMC3200780 PMID: 22064838

Abstract

The asymmetric unit of the title compound, C₂₁H₁₇Cl₂N₃O, contains two crystallographically independent molecules with similar conformations. The benzotriazole ring is oriented at dihedral angles of 30.61 (5) and 43.36 (5)°, respectively, to the phenyl and dichlorophenyl rings in one molecule, and 32.25 (5) and 41.04 (5)° in the other. The dihedral angles between the phenyl and dichlorophenyl rings are 66.38 (7) and 66.14 (6)° in the two molecules. An intramolecular O—H⋯N hydrogen bond links the benzotriazole ring and phenylpropanol unit in each molecule. In the crystal, weak intermolecular C—H⋯N hydrogen bonds link the molecules into chains along the a axis. π–π stacking between the dichlorophenyl rings [centroid–centroid distances = 3.809 (1) and 3.735 (1) Å] may further stabilize the crystal structure.

Related literature

For the biological activity of azole compounds, see: Cozzi et al. (1994 ▶) and of triazole derivatives, see: Jin et al. (2006 ▶). For related structures, see: Özel Güven et al. (2007 ▶, 2008 ▶, 2010 ▶).

Experimental

Crystal data

C₂₁H₁₇Cl₂N₃O
M _r = 398.28
Triclinic,
a = 9.3894 (2) Å
b = 9.4947 (2) Å
c = 21.2687 (3) Å
α = 91.415 (2)°
β = 92.324 (2)°
γ = 90.406 (1)°
V = 1893.90 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.36 mm⁻¹
T = 120 K
0.4 × 0.4 × 0.3 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T _min = 0.866, T _max = 0.897
40396 measured reflections
8697 independent reflections
7206 reflections with I > 2σ(I)
R _int = 0.044

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.108
S = 1.07
8697 reflections
487 parameters
H-atom parameters constrained
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.73 e Å⁻³

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811034738/xu5297sup1.cif

e-67-o2510-sup1.cif^{(31.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811034738/xu5297Isup2.hkl

e-67-o2510-Isup2.hkl^{(416.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811034738/xu5297Isup3.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
O1—H1A⋯N2	0.82	2.56	3.1254 (19)	127
O1′—H1B⋯N2′	0.82	2.52	3.0881 (19)	128
C19—H19⋯N3ⁱ	0.93	2.54	3.420 (2)	158
C19′—H19′⋯N3′ⁱⁱ	0.93	2.53	3.410 (2)	159

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

Acknowledgments

The authors acknowledge Zonguldak Karaelmas University Research Fund (project No: 2010-13-02-06).

supplementary crystallographic information

Comment

Azole compounds have important biological activities. In literature 2-(1H-imidazol-1-yl)-1,3-diphenylpropan-1-one and its derivatives have been reported that they show both high and selective thromboxane A2 receptor antagonist and thromboxane A2 synthase inhibitory activity (Cozzi et al., 1994). Some 1H-1,2,4-triazole derivatives have been known as antifungal and plant growth regulatory agents (Jin et al., 2006). Crystal structures of similar compounds like ketone having benzimidazole and furan rings (Özel Güven et al., 2007) and alcohols having 1,2,4-triazole and benzotriazole rings have been reported (Özel Güven et al., 2008; Özel Güven et al., 2010). Now, we report herein the crystal structure of the title benzotriazole derivative, (I).

The asymmetric unit of the title compound (Fig. 1) contains two crystallographically independent molecules, in which they differ slightly in the orientations of the 2-6-dichlorophenyl units and the bond lengths and angles are generally within normal ranges. The intramolecular O—H···N hydrogen bonds (Table 1) link the benzotriazole rings and phenylpropan units. In each molecule, the planar benzotriazole rings [A (N1-N3/C9-C14) and A' (N1'-N3'/C9'-C14')] are oriented with respect to the phenyl [B (C3-C8) and B' (C3'-C8')] and 2-6-dichlorophenyl [C (C16-C21)] and C' (C16'-C21')] rings at dihedral angles of A/B = 30.61 (5), A/C = 43.36 (5) ° and A'/B' = 32.25 (5), A'/C' = 41.04 (5) °. The dihedral angles between phenyl rings are B/C = 66.38 (7) and B'/C' = 66.14 (6) °. Atoms C1 and C1' are -0.044 (2) and 0.086 (2) Å away from the planes of the benzotriazole rings, respectively.

In the crystal structure, intermolecular C—H···N hydrogen bonds (Table 1) link the molecules into chains along the a-axis (Fig. 2). The π–π contacts between the 2-6-dichlorophenyl rings, Cg3—Cg3ⁱ and Cg3'—Cg3'ⁱⁱ, [symmetry codes: (i) 2 - x, 2 - y, - z, (ii) 1 - x, 1 - y, 1 - z, where Cg3 and Cg3' are the centroids of the rings C (C16-C21)] and C' (C16'-C21'), respectively], may further stabilize the structure, with centroid-centroid distances of 3.809 (1) and 3.735 (1) Å, respectively.

Experimental

The title compound, (I), was synthesized by the reduction of 2-(1H-benzotriazol-1-yl)-3-(2,6-dichlorophenyl)-1-phenylpropane-1-one. Sodiumborohydride (38.21 mg, 1.01 mmol) was added to a solution of 2-(1H-benzotriazol-1-yl)-3-(2,6-dichlorophenyl)-1-phenylpropane-1-one (200 mg, 0.505 mmol) in ethanol (15 ml). The mixture was refluxed for 5 h. The solvent was removed and the mixture was neutralized with dilute HCl, and then refluxed for 30 min. After cooling the mixture, it was alkalinized with dilute NaOH. The precipitate was filtered and washed with ethanol. The filtrate was extracted with chloroform, then the organic phase was dried and solvents were removed by rotary evaporator. The residue was purified with column chromatography using hexane: ethyl acetate (7:3) mixture as solvent. The product was crystallized from benzene to obtain colorless single crystals suitable for X-ray analysis (yield; 82 mg, 41%).