2-(1H-Benzotriazol-1-yl)-1-(4-bromo­benzo­yl)ethyl 2-chloro­benzoate

Kong-Cheng Hu; Guang-Jiu Li

doi:10.1107/S1600536809002712

. 2009 Jan 31;65(Pt 2):o443. doi: 10.1107/S1600536809002712

2-(1H-Benzotriazol-1-yl)-1-(4-bromobenzoyl)ethyl 2-chlorobenzoate

Kong-Cheng Hu ^a, Guang-Jiu Li ^a,^*

PMCID: PMC2968311 PMID: 21582028

Abstract

In the title compound, C₂₂H₁₅BrClN₃O₃, the benzotriazole ring system makes dihedral angles of 2.43 (1) and 71.51 (1)° with the bromophenyl and chlorophenyl rings, respectively; the angle between the latter two rings is 69.26 (1)°. In the crystal structure, molecules are linked into chains by intermolecular C—H⋯O hydrogen bonds. The crystal packing is further stabilized by π–π (with a centroid-centroid distance of 3.764 Å) and C—H⋯π interactions.

Related literature

For the crystal structure of a related compound, see: Zeng et al. (2007 ▶). For standard bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₂₂H₁₅BrClN₃O₃
M _r = 484.72
Monoclinic,
a = 6.2613 (7) Å
b = 36.688 (4) Å
c = 8.7919 (9) Å
β = 90.878 (2)°
V = 2019.4 (4) Å³
Z = 4
Mo Kα radiation
μ = 2.20 mm⁻¹
T = 293 (2) K
0.36 × 0.21 × 0.09 mm

Data collection

Siemens SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.505, T _max = 0.827
11039 measured reflections
3978 independent reflections
2968 reflections with I > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.103
S = 1.04
3978 reflections
271 parameters
H-atom parameters constrained
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); 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, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2003 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809002712/wn2306sup1.cif

e-65-0o443-sup1.cif^{(21.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809002712/wn2306Isup2.hkl

e-65-0o443-Isup2.hkl^{(195KB, hkl)}

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

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

Cg1 is the centroid of the N1–N3/C17/C18 triazole ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16A⋯Cg1ⁱ	0.93	2.87	3.707	150
C21—H21A⋯O3ⁱⁱ	0.93	2.47	3.101 (4)	126

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

Acknowledgments

This project was supported by the Natural Science Foundation of Shandong Province (grant Nos. Y2008B02 and Y2008B32).

supplementary crystallographic information

Comment

The crystal structure of 2-(benzotriazol-1-yl)-1-(4-methylbenzoyl)ethyl 4-ethylbenzoate has been reported by Zeng et al. (2007). In a search for new benzotriazole derivatives with higher bioactivity, the title compound was synthesized and its structure is reported here.

In the title molecule (Fig. 1), all bond lengths (Allen et al., 1987) and angles are within normal ranges. The benzotriazole system is almost planar, with a dihedral angle of 0.89 (1)° between the triazole ring (N1–N3/C17/C18) and the benzene ring A (C17–C22). The benzotriazole mean plane makes dihedral angles of 2.43 (1)° and 71.51 (1)° with benzene rings B (C1–C6) and C (C11–C16), respectively, indicating the non-planarity of the whole molecule. The dihedral angle between rings B and C is 69.26 (1)°.

In the crystal structure (Fig. 2), molecules are linked into chains along the c axis by intermolecular C21—H21A···O3 hydrogen bonds (Table 1). The distance of 3.764 Å between the centroids of rings A and B related by the symmetry code (x, y, -1 + z) suggests a possible π···π interaction. The crystal packing is further stabilized by C—H···π interactions (Table 1).

Experimental

The title compound was prepared according to the literature method of Zeng et al. (2007). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of an ethyl acetate solution at room temperature over a period of six days.