(E)-1-(1H-Benzotriazol-1-yl 3-oxide)-3-methoxy­but-2-en-1-one

Jiu-Ming Li; Jian-Ping Yong

doi:10.1107/S1600536809050442

. 2009 Dec 4;66(Pt 1):o13. doi: 10.1107/S1600536809050442

(E)-1-(1H-Benzotriazol-1-yl 3-oxide)-3-methoxybut-2-en-1-one

Jiu-Ming Li ^a,^*, Jian-Ping Yong ^b

PMCID: PMC2980092 PMID: 21580020

Abstract

The title compound, C₁₁H₁₁N₃O₃, crystallizes with two independent molecules of similar geometry in the asymmetric unit. The molecular conformations are stabilized by intramolecular C—H⋯O hydrogen bonds. The crystal packing consists of wave-like layers parallel to the bc plane formed by intermolecular C—H⋯O hydrogen-bonding interactions involving only one independent molecule.

Related literature

For related structures, see: Barlos et al. (1985 ▶); Singh et al. (1988 ▶). For details of the biological activity of benzentriazol-containing compounds, see: Zhang et al. (2002 ▶). For comparative bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₁H₁₁N₃O₃
M _r = 233.23
Monoclinic,
a = 14.011 (3) Å
b = 10.014 (2) Å
c = 15.699 (3) Å
β = 100.13 (3)°
V = 2168.3 (8) Å³
Z = 8
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 173 K
0.40 × 0.40 × 0.30 mm

Data collection

Rigaku Mercury CCD/AFC diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007 ▶) T _min = 0.959, T _max = 0.969
15367 measured reflections
3771 independent reflections
3564 reflections with I > 2σ(I)
R _int = 0.050

Refinement

R[F ² > 2σ(F ²)] = 0.063
wR(F ²) = 0.141
S = 1.17
3771 reflections
308 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Data collection: CrystalClear (Rigaku, 2007 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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 I, global. DOI: 10.1107/S1600536809050442/rz2397sup1.cif

e-66-00o13-sup1.cif^{(23KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809050442/rz2397Isup2.hkl

e-66-00o13-Isup2.hkl^{(184.9KB, 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
C2—H2B⋯O2	0.95	2.45	2.925 (3)	111
C13—H13A⋯O5	0.95	2.49	2.961 (3)	111
C14—H14A⋯O4ⁱ	0.95	2.57	3.398 (3)	147
C16—H16A⋯O4ⁱⁱ	0.95	2.45	3.379 (3)	165

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

supplementary crystallographic information

Comment

Benzotriazole derivatives exhibit good pharmacological activities and a wide spectrum of biological activities (Zhang et al., 2002). In order to search for new benzotriazole compounds with higher bioactivity, we synthesized the title compound and describe its structure here.

The asymmetric unit of the title compound (Fig. 1) contains two independent molecules of similar geometry. The molecules are almost planar, the maximum deviation being 0.110 (2) Å for atom O2 in one molecule and 0.093 (3) Å for atom C22 in the other molecule. All bond lengths in the molecules are normal (Allen et al., 1987) and in a good agreement with those reported previously for related compound (Barlos et al., 1985; Singh et al., 1988). The molecular conformations are stabilized by intramolecular C—H···O hydrogen bonds (Table 1). In the crystal packing, molecules containing the N4–N6 nitrogen atoms are linked by intermolecular C—H···O hydrogen bonds to form wavy layers parallel to the bc plane intersecting each other.

Experimental

3-Methoxycrotonic acid (20 mmol) was dissolved in dichloromethane and cooled to 273 K, then 1-hydroxybenzotriazole (30 mmol) was added in one portion. After 10 h stirring at room temperature, the solution was washed successively with 1 N HCl and saturated NaCl, and the organic layer was separated, dried with Na₂SO₄ and evaporated to obtain the primary product. The pure compound was isolated by column chromatography (3.4 g, yield 73%). Single crystals suitable for X-ray measurements were obtained by slow evaporation of an ethyl acetate solution at room temperature. ¹H NMR (400 MHz, CDCl3) δ: 8.49 (d, J = 8 Hz, 1H), 7.99 (d, J = 8 Hz, 1H), 7.75 (t, 1H), 7.53 (t, 1H), 6.30 (s, 1H), 3.85 (s, 3H), 2.50 (s, 3H).