N′-[1-(4-Chloro­phen­yl)ethyl­idene]-5-methyl-1-(4-nitro­phen­yl)-1H-1,2,3-triazole-4-carbohydrazide

Hoong-Kun Fun; Ching Kheng Quah; Nitinchandra; Balakrishna Kalluraya; Shobhitha Shetty

doi:10.1107/S1600536812027535

. 2012 Jun 23;68(Pt 7):o2164. doi: 10.1107/S1600536812027535

N′-[1-(4-Chlorophenyl)ethylidene]-5-methyl-1-(4-nitrophenyl)-1H-1,2,3-triazole-4-carbohydrazide

Hoong-Kun Fun ^a,^*,^‡, Ching Kheng Quah ^a,^§, Nitinchandra ^b, Balakrishna Kalluraya ^b, Shobhitha Shetty ^b

PMCID: PMC3393971 PMID: 22798836

Abstract

In the title compound, C₁₈H₁₅ClN₆O₃, the 1,2,3-triazole ring forms dihedral angles of 15.64 (5) and 57.50 (5)° with the two benzene rings. The dihedral angle between the two benzene rings is 72.26 (5)°. In the crystal, molecules are linked via C—H⋯O hydrogen bonds into chains propagating along the b axis. A short O⋯C contact of 2.9972 (13) Å is observed.

Related literature

For general background to and the biological activity of triazole derivatives, see: Sherement et al. (2004 ▶); Danoun et al. (1998 ▶); Manfredini et al. (2000 ▶); Biagi et al. (2004 ▶); Vijayakumar et al. (2011 ▶). For standard bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶). For related structures, see: Fun, Quah, Chandrakantha et al. (2011 ▶); Fun et al. (2011a ▶,b ▶).

Experimental

Crystal data

C₁₈H₁₅ClN₆O₃
M _r = 398.81
Triclinic,
a = 8.6603 (1) Å
b = 10.2844 (1) Å
c = 10.4033 (1) Å
α = 83.816 (1)°
β = 81.402 (1)°
γ = 76.373 (1)°
V = 887.84 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 100 K
0.31 × 0.19 × 0.17 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.927, T _max = 0.958
29293 measured reflections
7839 independent reflections
6598 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.120
S = 1.03
7839 reflections
259 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.45 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812027535/is5158sup1.cif

e-68-o2164-sup1.cif^{(27.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812027535/is5158Isup2.hkl

e-68-o2164-Isup2.hkl^{(383.5KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812027535/is5158Isup3.cml

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
C13—H13A⋯O1ⁱ	0.95	2.32	3.2226 (12)	158

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank Universiti Sains Malaysia (USM) for the Research University Grant (No. 1001/PFIZIK/811160). CKQ also thanks USM for an Incentive Grant. BK thanks the Department of Atomic Energy, Board for Research in Nuclear Sciences, Government of India, for financial assistance.

supplementary crystallographic information

Comment

1,2,3-Triazole and its derivatives had attracted considerable attention for the past few decades due to their chemotherapeutic value. Many 1,2,3-triazoles are found to be potent antimicrobial (Sherement et al., 2004) and antiviral agents. Some of them have exhibited antiproliferative and anticancer activities (Danoun et al., 1998). Some 1,2,3-triazoles are used as DNA cleaving agents (Manfredini et al., 2000) and potassium channel activators (Biagi et al., 2004). Hydrazones derived from anisaldehyde and 4-nitro-5-ethoxycarbonyl phenylhydrazine showed excellent NLO property (Vijayakumar et al., 2011). Prompted by these observation, we synthesized new hydrazone carrying 1,2,3-triazoles nucleus.

In the title molecule, Fig. 1, the mean plane of 1,2,3-triazole ring (N3-N5/C9/C10, r.m.s deviation = 0.002 Å) forms dihedral angles of 15.64 (5) and 57.50 (5)° with the two benzene rings (C1–C6 and C11–C16). The dihedral angle between the two benzenel rings is 72.26 (5)°. Bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to related structures (Fun, Quah, Chandrakantha et al., 2011; Fun et al., 2011a,b). In the crystal (Fig. 2), molecules are linked via intermolecular C13—H13A···O1 hydrogen bonds (Table 1) into chains propagating along [010]. A short O2···C7 contact of 2.9972 (13) Å also occurs.

Experimental

The title compound was obtained by refluxing a mixture of 5-methyl-1-(4-nitrophenyl)-1H-1,2,3-triazole-4-carbohydrazide (0.01 mol) and p-chloroacetophenone (0.01 mol) in ethanol (30 ml) and 3 drops of concentrated sulfuric acid for 1 h. Excess ethanol was removed from the reaction mixture under reduced pressure. The solid product obtained was filtered, washed with ethanol and dried. Single crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol-N,N-dimethylformamide (DMF) (3:1) solution.