2-(1H-Benzotriazol-1-yl)-1-(2-fluoro­benzo­yl)ethyl 4-methyl­benzoate

Wu-Lan Zeng; Fang-Fang Jian

doi:10.1107/S1600536809029481

. 2009 Jul 29;65(Pt 8):o2036. doi: 10.1107/S1600536809029481

2-(1H-Benzotriazol-1-yl)-1-(2-fluorobenzoyl)ethyl 4-methylbenzoate

Wu-Lan Zeng ^a, Fang-Fang Jian ^a,^*

PMCID: PMC2977322 PMID: 21583702

Abstract

In the crystal structure of the title compound, C₂₃H₁₈FN₃O₃, intermolecular C—H⋯N hydrogen bonds link the molecules into chains extended along the c axis. The packing is further stabilized by weak C—H⋯O and C—H⋯F interactions. The F atom is disordered over two equally occupied 1- and 5-positions of the benzene ring.

Related literature

For the pharmacological activity of 1H-benzotriazole and its derivatives, see: Chen & Wu (2005 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₂₃H₁₈FN₃O₃
M _r = 403.40
Monoclinic,
a = 20.478 (4) Å
b = 19.570 (4) Å
c = 9.969 (2) Å
β = 107.12 (3)°
V = 3818.0 (13) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.10 × 0.06 × 0.02 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T _min = 0.990, T _max = 0.998
19476 measured reflections
3368 independent reflections
2698 reflections with I > 2σ(I)
R _int = 0.058

Refinement

R[F ² > 2σ(F ²)] = 0.064
wR(F ²) = 0.177
S = 1.08
3368 reflections
282 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.27 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/S1600536809029481/at2823sup1.cif

e-65-o2036-sup1.cif^{(22.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809029481/at2823Isup2.hkl

e-65-o2036-Isup2.hkl^{(165.3KB, 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
C8—H8⋯F1	0.98	2.24	2.938 (5)	127
C9—H9A⋯N2ⁱ	0.97	2.55	3.515 (3)	174
C12—H12⋯O1ⁱⁱ	0.93	2.48	3.118 (4)	126
C22—H22⋯O3ⁱⁱⁱ	0.93	2.48	3.259 (4)	142
C23—H23C⋯F1′^iv	0.96	2.37	3.090 (5)	131

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

Acknowledgments

This research has been supported by the Foundation of Weifang University.

supplementary crystallographic information

Comment

1H-Benzotriazoles and its derivatives are an important class of compounds because they 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.

All the bond lengths (Allen et al., 1987) and angles in (I) are within their normal ranges. The dihedral angle between the triazole ring (N1–N3/C10/C15) and the benzene ring (C10–C15) is 2.86 (12)°. The dihedral angles between the triazole ring and the C1–C6 and C17–C22 aromatic rings are 4.78 (13)° and 65.34 (13)°, respectively. The dihedral angle between the C1—C6 and C17–C22 rings is 62.04 (14)°. Molecule (I) is chiral. In the crystal structure, intermolecular C—H···N hydrogen bonds (Table1) link the molecules into chains extended along the c axis. The packing (Fig. 2) is further stabilized by weak C—H···O and C—H···F interactions (Table 1).

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-(2-fluorophenyl)propan-1-one (5.38 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 4-methylbenzoic acid (2.72 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. Single crystals of (I) were obtained by slow evaporation of an acetone-ethylacetate (3:1 v/v) solution at room temperature over a period of one week.