2-(1H-1,2,3-Benzotriazol-1-yl)-N′-(2-chloro­benzyl­idene)acetohydrazide

Guo-Fang He; Zhi-Qiang Shi

doi:10.1107/S1600536810050440

. 2010 Dec 8;67(Pt 1):o48. doi: 10.1107/S1600536810050440

2-(1H-1,2,3-Benzotriazol-1-yl)-N′-(2-chlorobenzylidene)acetohydrazide

Guo-Fang He ^a,^*, Zhi-Qiang Shi ^a

PMCID: PMC3050203 PMID: 21522757

Abstract

In the title compound, C₁₅H₁₂ClN₅O, the mean planes of the benzotriazole and chlorophenyl fragments form a dihedral angle of 70.8 (1)°. In the crystal, molecules are linked into infinite chains along the a axis by N—H⋯O hydrogen bonds. Weak intermolecular C—H⋯N hydrogen bonds further link these chains into layers parallel to the ab plane. The crystal studied was a racemic twin.

Related literature

For related structures, see: Shi et al. (2007a ▶,b ▶); Ji & Shi (2008 ▶).

Experimental

Crystal data

C₁₅H₁₂ClN₅O
M _r = 313.75
Monoclinic,
a = 4.6777 (16) Å
b = 11.726 (4) Å
c = 13.328 (5) Å
β = 94.224 (7)°
V = 729.0 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 295 K
0.12 × 0.10 × 0.08 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.968, T _max = 0.979
3851 measured reflections
1902 independent reflections
1370 reflections with I > 2σ(I)
R _int = 0.039

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.089
S = 1.01
1902 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.17 e Å⁻³
Absolute structure: Flack (1983 ▶), 544 Flack pairs
Flack parameter: 0.55 (11)

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810050440/cv5009sup1.cif

e-67-00o48-sup1.cif^{(17.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810050440/cv5009Isup2.hkl

e-67-00o48-Isup2.hkl^{(93.6KB, 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
N4—H4⋯O1ⁱ	0.86	2.04	2.841 (4)	154
C7—H7A⋯N3ⁱⁱ	0.97	2.48	3.320 (6)	145

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

Acknowledgments

This work was supported by Taian City Science and Technology Bureau (grant No. 20081009).

supplementary crystallographic information

Comment

In continuation of our structural studies of benzotriazole derivatives (Shi et al., 2007a,b; Ji et al., 2008), herewith we present the crystal structure of the title compound, (I).

In (I) (Fig. 1), the bond lengths and angles are normal and in a good agreement with those observed in the related compounds (Shi et al., 2007a,b; Ji et al., 2008). The mean planes of the benzotriazole and chlorophenyl fragments form a dihedral angle of 70.8 (1)°.

In the crystal structure, the molecules are linked into infinite chains along the a axis by N—H···O hydrogen bonds (Table 1; Fig. 2). Weak intermolecular C—H···N hydrogen bonds (Table 1) link further these chains into layers parallel to ab plane.

Experimental

The title compound was synthesized by the reaction of 2-(1H-1,2,3-benzotriazol-1-yl)acetohydrazide (1 mmol, 191.2 mg) with 2-chlorobenzaldehyde(1 mmol, 140.6 mg) in ethanol(20 ml)under reflux conditions (348 K) for 5 h. The solvent was removed and the solid product recrystallized from tetrahydrofuran. After five days colourless crystals suitable for X-ray diffraction study were obtained.