2-(1H-Benzotriazol-1-yl)-1-(3-methoxy­benzo­yl)ethyl isonicotinate

Wei Wang; Zhen-Hua Mei

doi:10.1107/S1600536809001196

. 2009 Jan 23;65(Pt 2):o357. doi: 10.1107/S1600536809001196

2-(1H-Benzotriazol-1-yl)-1-(3-methoxybenzoyl)ethyl isonicotinate

Wei Wang ^a, Zhen-Hua Mei ^a,^*

PMCID: PMC2968212 PMID: 21581956

Abstract

In the title compound, C₂₂H₁₈N₄O₄, molecules are linked to each other by C—H⋯N and C—H⋯O intermolecular hydrogen-bonding interactions. The crystal packing is further stabilized by C—H⋯π, and π–π interactions with a distance of 3.783 (3) Å between the centroids of the benzene rings of the benzotriazole system.

Related literature

For general background on benzotriazole and its derivatives, see: Chen & Wu (2005 ▶). For details of the synthesis, see: Wan et al. (2006 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₂₂H₁₈N₄O₄
M _r = 402.40
Triclinic,
a = 9.4839 (18) Å
b = 10.3611 (19) Å
c = 11.276 (2) Å
α = 109.342 (3)°
β = 102.664 (3)°
γ = 97.985 (3)°
V = 992.8 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 (2) K
0.33 × 0.16 × 0.08 mm

Data collection

Siemens SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.969, T _max = 0.992
5605 measured reflections
3819 independent reflections
2822 reflections with I > 2σ(I)
R _int = 0.013

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.119
S = 1.04
3819 reflections
271 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.19 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/S1600536809001196/at2705sup1.cif

e-65-0o357-sup1.cif^{(21.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809001196/at2705Isup2.hkl

e-65-0o357-Isup2.hkl^{(187.2KB, hkl)}

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

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

Cg3 and Cg4 are the centroids of the C1–C6 and C10–C15 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3B⋯N3ⁱ	0.93	2.48	3.328 (3)	151
C9—H9B⋯O1ⁱⁱ	0.97	2.56	3.471 (2)	157
C15—H15A⋯O1ⁱⁱ	0.93	2.46	3.368 (3)	164
C20—H20A⋯Cg3ⁱⁱⁱ	0.93	2.85	3.767	168
C22—H22C⋯Cg4^iv	0.96	2.87	3.530	127

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

Acknowledgments

This project was supported by the Natural Science Foundation of Shandong Province (grant No. Y2006B07).

supplementary crystallographic information

Comment

Benzotriazole and its derivatives exhibit an excellent pharmacological activities, such as antifungal, antitumor and antineoplastic activities (Chen & Wu, 2005). In order to find a new benzotriazole compound with higher bioactivity, the title compound, (I) (Fig. 1), was synthesized and its crystal structure was presented here.

In (I), all bond lengths and angles are within normal ranges (Allen et al., 1987). The benzotriazole ring is mostly planar with a dihedral angle of 1.75 (1)° between the N1—N3/C10/C11 triazole and C10—C15 benzene rings. The mean plane makes dihedral angles of 70.93 (1) and 19.8 (1)° with the N4/C17—C21 pyridine and C1—C6 benzene rings, respectively, and the dihedral angle between the latter two aromatic rings is 80.08 (1)°.

In the crystal structure, molecules of (I) are linked to each other by C3—H3B···N3, and further linked by C—H···O intermolecular hydrogen bonding interactions (C9—H9B···O1 and C15—H15A···O1), and stabilized by C—H···π interactions (Table 1). The distances of 3.783 Å between the centroids of the rings C10—C15 related by the symmetry code (-x, 1 - y, 1 - z) suggests a possible π–π interaction.

Experimental

The title compound was prepared according to the literature method of Wan et al. (20067). 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.