N′-(3,4-Dichloro­benzyl­idene)-5-methyl-1-(4-nitro­phen­yl)-1H-1,2,3-triazole-4-carbohydrazide

Hoong-Kun Fun; Suhana Arshad; Nithinchandra; Balakrishna Kalluraya; J H S Vidyashree

doi:10.1107/S1600536812023112

. 2012 May 26;68(Pt 6):o1902. doi: 10.1107/S1600536812023112

N′-(3,4-Dichlorobenzylidene)-5-methyl-1-(4-nitrophenyl)-1H-1,2,3-triazole-4-carbohydrazide

Hoong-Kun Fun ^a,^*,^‡, Suhana Arshad ^a, Nithinchandra ^b, Balakrishna Kalluraya ^b, J H S Vidyashree ^b

PMCID: PMC3379459 PMID: 22719657

Abstract

In the title compound, C₁₇H₁₂Cl₂N₆O₃, the 1H-1,2,3-triazole ring [maximum deviation = 0.003 (1) Å] forms dihedral angles of 34.08 (6) and 28.38 (6)°, respectively, with the nitro- and dichloro-substituted benzene rings. The dihedral angle between the benzene rings is 6.68 (5)°. In the crystal, C—H⋯O hydrogen bonds link the molecules into chains running parallel to the a axis.

Related literature

For aryl hydrazones, see: Sridhar & Perumal (2003 ▶); Bedia et al. (2006 ▶); Rollas et al. (2002 ▶); Terzioglu & Gürsoy (2003 ▶). For related structures, see: Fun et al. (2011 ▶); Wang et al. (2010 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶). graphic file with name e-68-o1902-scheme1.jpg

Experimental

Crystal data

C₁₇H₁₂Cl₂N₆O₃
M _r = 419.23
Monoclinic,
a = 6.6309 (3) Å
b = 22.7059 (10) Å
c = 13.3019 (5) Å
β = 119.559 (2)°
V = 1742.08 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.41 mm⁻¹
T = 100 K
0.43 × 0.15 × 0.08 mm

Data collection

Bruker SMART APEX DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.844, T _max = 0.967
38004 measured reflections
6085 independent reflections
5280 reflections with I > 2σ(I)
R _int = 0.030

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.099
S = 1.04
6085 reflections
258 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.64 e Å⁻³
Δρ_min = −0.46 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/S1600536812023112/hb6804sup1.cif

e-68-o1902-sup1.cif^{(26.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812023112/hb6804Isup2.hkl

e-68-o1902-Isup2.hkl^{(297.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812023112/hb6804Isup3.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
C10—H10A⋯O3ⁱ	0.93	2.41	3.2649 (17)	153
C12—H12A⋯O3ⁱ	0.93	2.59	3.4076 (15)	147

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). SA also thanks the Malaysian Government and USM for the Academic Staff Training Scheme (ASTS) award. BK is thankful to the Department of Atomic Energy, Board for Research in Nuclear Sciences, Government of India, for financial assistance.

supplementary crystallographic information

Comment

Aryl hydrazones are important building blocks for the synthesis of a variety of heterocyclic compounds such as pyrazolines and pyrazoles (Sridhar & Perumal, 2003). Aryl hydrazones have been most conveniently synthesized by the reaction of aryl hydrazines with carbonyl compounds. Hydrazones possessing an azomethine —NHN═CH— proton constitute an important class of compound for new drug development. Hydrazones have been demonstrated to possess anti-microbial, anti-convulsant, analgesic, anti-inflammatory, anti-platelet, anti-tubercular, anti-cancer and anti-tumoral activities (Bedia et al., 2006; Rollas et al., 2002; Terzioglu & Gürsoy, 2003). Prompted by these observations, the title compound was synthesized and its crystal structure is reported here.

The molecular structure is shown in Fig. 1. The 1H-1,2,3-triazole ring [N2–N4/C7/C8; maximum deviation of 0.003 (1) Å at atom N3] forms dihedral angles of 34.08 (6) and 28.38 (6)°, respectively with the nitro-substituted and dichloro-substituted phenyl rings (C1–C6 and C11–C16). The dihedral angle between the nitro-substituted (C1–C6) and dichloro-substituted (C11–C16) phenyl rings is 6.68 (5)°. Bond lengths and angles are within normal ranges and comparable to the related structures (Fun et al., 2011; Wang et al., 2010).

The crystal packing is shown in Fig. 2. The molecules are linked via intermolecular C10—H10A···O3 and C12—H12A···O3 hydrogen bonds (Table 1) into one-dimensional chain parallel to a-axis.

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), 3,4-dichlorobenzaldehyde (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. Colourless plates were obtained by slow evaporation of an ethanol-N,N- dimethylformamide (DMF) (3:1) solution.