2-(1H-1,2,3-Benzotriazol-1-yl)-1-m-toluoylethyl 2,4-dichloro­benzoate

Wu-Lan Zeng

doi:10.1107/S1600536808011963

. 2008 Apr 30;64(Pt 5):o941. doi: 10.1107/S1600536808011963

2-(1H-1,2,3-Benzotriazol-1-yl)-1-m-toluoylethyl 2,4-dichlorobenzoate

Wu-Lan Zeng ^a,^*

PMCID: PMC2961103 PMID: 21202422

Abstract

In the title compound, C₂₃H₁₇Cl₂N₃O₃, the dihedral angles between the mean planes of the benzotriazole system and the methyl- and dichloro-substituted benzene rings are 47.72 (1) and 13.06 (1)°, respectively. In the crystal structure, intermolecular C—H⋯O and C—H⋯π interactions help to consolidate the packing.

Related literature

For background, see Chen & Wu (2005 ▶). For reference structural data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₂₃H₁₇Cl₂N₃O₃
M _r = 454.30
Monoclinic,
a = 9.3395 (19) Å
b = 9.3065 (19) Å
c = 23.538 (5) Å
β = 92.10 (3)°
V = 2044.5 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.35 mm⁻¹
T = 113 (2) K
0.18 × 0.16 × 0.08 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T _min = 0.940, T _max = 0.973
11260 measured reflections
3585 independent reflections
3138 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.033
wR(F ²) = 0.091
S = 1.10
3585 reflections
281 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); 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 datablocks global, I. DOI: 10.1107/S1600536808011963/hb2721sup1.cif

e-64-0o941-sup1.cif^{(21.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808011963/hb2721Isup2.hkl

e-64-0o941-Isup2.hkl^{(175.8KB, hkl)}

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
C15—H15⋯O1ⁱ	0.93	2.35	3.263 (2)	168
C4—H4⋯Cg1ⁱⁱ	0.93	2.86	3.4645 (19)	124

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Symmetry codes: (i) Inline graphic ; (ii) . Cg1 is the centroid of the C18–C23 ring.

supplementary crystallographic information

Comment

1H-Benzotriazole and its derivatives exhibit a broad spectrum of pharmacological activities such as antifungal, antitumor and antineoplastic activities (Chen & Wu, 2005). We report here the synthesis and structure of the title compound, (I) (Fig. 1), as part of our ongoing studies on new benzotriazole compounds with higher bioactivity.

The molecule of (I) is chiral. In the arbitrarily chosen asymmetric molecule, C9 has S configuration, but crystal symmetry generates a racemic mixture. Otherwise, all the bond lengths and angles in (I) are within their normal ranges (Allen et al., 1987). The benzotriazole ring system is essentially planar, with a dihedral angle of 2.2 (8)° between the triazole ring (atoms N1—N3/C18/C23) and the C18—C23 benzene ring. The dihedral angles between the mean planes of the benzotriazole system and the C1—C6 and C11—C15 aromatic rings are 47.72 (1)° and 13.06 (1)°, respectively. The dihedral angle between rings C1—C6 and C11—C15 is 35.26 (2)°.

In the crystal, intermolecular C-H···O and C-H···π interactions (Table 1) help to consolidate the packing.

Experimental

Bromine (3.2 g, 0.02 mol) was added dropwise to a solution of 3-(1H-benzo[d][1,2,3]triazol-1-yl)-1-m-tolylpropan-1-one (5.30 g, 0.02 mol) and sodium acetate (1.6 g, 0.02 mol) in acetic acid (50 ml). The reaction proceeded for 7 h. Water (50 ml) and chloroform (20 ml) were then added. The organic layer was washed successively with saturated sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate and the chloroform solution filtered. It was cooled with ice-water, and then an acetone solution (10 ml) of 2-chlorobenzoic acid (3.8 g, 0.02 mol) and triethylamine (2.8 ml) was added. The mixture was stirred with ice-water for 6 h. The solution was then filtered and concentrated. Colourless slabs of (I) were obtained by slow evaporation of ethanol solution at room temperature after one week.