3-(1H-Benzotriazol-1-yl)-1-(3-methoxy­phen­yl)propan-1-one

Guang-Jiu Li; Kong-Cheng Hu

doi:10.1107/S1600536809004127

. 2009 Feb 11;65(Pt 3):o507. doi: 10.1107/S1600536809004127

3-(1H-Benzotriazol-1-yl)-1-(3-methoxyphenyl)propan-1-one

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

PMCID: PMC2968644 PMID: 21582170

Abstract

In the title molecule, C₁₆H₁₅N₃O₂, the benzotriazole fragment and the benzene ring form a dihedral angle of 75.02 (1)°. In the crystal structure, molecules related by translation along the a axis are linked into chains via weak C—H⋯π interactions.

Related literature

For the pharmacological activity of 1H-benzotriazole derivatives, see: Chen & Wu (2005 ▶). Some details of the synthesis have been described by Zhu et al. (2007 ▶). For reference values of geometric parameters in organic molecules, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₆H₁₅N₃O₂
M _r = 281.31
Monoclinic,
a = 5.3583 (14) Å
b = 12.976 (4) Å
c = 19.688 (5) Å
β = 91.146 (4)°
V = 1368.6 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 (2) K
0.21 × 0.15 × 0.07 mm

Data collection

Siemens SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.981, T _max = 0.994
7461 measured reflections
2693 independent reflections
2279 reflections with I > 2σ(I)
R _int = 0.018

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.112
S = 1.04
2693 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.23 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/S1600536809004127/cv2510sup1.cif

e-65-0o507-sup1.cif^{(18.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809004127/cv2510Isup2.hkl

e-65-0o507-Isup2.hkl^{(132.2KB, 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
C9—H9A⋯Cg1ⁱ	0.97	2.74	3.504	136

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Symmetry code: (i) Inline graphic . Cg1 is the centroid of atoms C10–C15.

Acknowledgments

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

supplementary crystallographic information

Comment

1H-Benzotriazole and its derivatives exhibit a broad spectrum of pharmacological activities, such as antifungal, antitumor and antineoplastic (Chen & Wu, 2005). In order to search for new benzotriazole derivatives with higher bioactivity, the title compound, (I), was synthesized and its structure is shown here.

In the title molecule (Fig. 1), all bond lengths and angles are within normal ranges (Allen et al., 1987). The benzotriazole system is almost planar with a dihedral angle of 1.45 (1)° between the triazole (N1–N3/C10/C11) and benzene (C10—C15) rings. The whole molecular is non-planar with a dihedral angle of 75.02 (1)° between the benzotriazole fragment and benzene C1–C6 ring. In the crystal, the molecules related by translation along axis a are linked into chains via the weak C—H···π interactions (Table 1).

Experimental

The title compound was prepared according to the literature method of Zhu 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 one week.