(2E)-1-[2,3-Dichloro-6-methyl-5-(trifluoro­meth­yl)phen­yl]-2-(1-phenyl­ethyl­idene)hydrazine

Hoong-Kun Fun; Wan-Sin Loh; Manjunath Bhat; T Arulmoli; G K Nagaraja

doi:10.1107/S1600536812042419

. 2012 Oct 20;68(Pt 11):o3189. doi: 10.1107/S1600536812042419

(2E)-1-[2,3-Dichloro-6-methyl-5-(trifluoromethyl)phenyl]-2-(1-phenylethylidene)hydrazine

Hoong-Kun Fun ^a,^b,^*,^‡, Wan-Sin Loh ^a,^§, Manjunath Bhat ^c,^d, T Arulmoli ^c, G K Nagaraja ^d

PMCID: PMC3515280 PMID: 23284500

Abstract

The title compound, C₁₆H₁₃Cl₂F₃N₂, exists in an E conformation with respect to the C=N bond [1.2952 (11) Å] and the C—N—N=C torsion angle is 175.65 (8)°. The dihedral angle between the benzene rings is 42.09 (4)°. An intramolecular C—H⋯F hydrogen bond generates an S(6) ring. In the crystal, the molecules are linked into [101] chains by C—H⋯F hydrogen bonds.

Related literature

For background to the properties and applications of hydrazones, see: Barbazan et al. (2008 ▶); Banerjee et al. (2009 ▶); Ghavtadze et al. (2008 ▶). For related structures, see: Fun et al. (2011a ▶,b ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₁₆H₁₃Cl₂F₃N₂
M _r = 361.18
Monoclinic,
a = 11.2600 (16) Å
b = 11.4025 (17) Å
c = 14.8398 (16) Å
β = 123.773 (7)°
V = 1583.8 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.44 mm⁻¹
T = 100 K
0.32 × 0.26 × 0.22 mm

Data collection

Bruker SMART APEXII Duo CCD diffractometer
Absorption correction: multi-scan (SADABS); Bruker, 2009 ▶) T _min = 0.872, T _max = 0.911
22269 measured reflections
5714 independent reflections
5043 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.029
wR(F ²) = 0.090
S = 1.02
5714 reflections
210 parameters
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.27 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, PLATON (Spek, 2009 ▶).

Supplementary Material

Click here for additional data file.^{(25.3KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812042419/hb6964sup1.cif

e-68-o3189-sup1.cif^{(25.3KB, cif)}

Click here for additional data file.^{(279.8KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812042419/hb6964Isup2.hkl

e-68-o3189-Isup2.hkl^{(279.8KB, hkl)}

Click here for additional data file.^{(6KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536812042419/hb6964Isup3.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
C1—H1A⋯F1ⁱ	0.95	2.39	3.1652 (14)	139
C15—H15A⋯F2	0.98	2.38	3.1018 (13)	130

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Symmetry code: (i) Inline graphic .

Acknowledgments

HKF and WSL thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). WSL also thanks the Malaysian Government and USM for the position of Research Officer under the Research University Grant (1001/PFIZIK/811160).

supplementary crystallographic information

Comment

Hydrazones are important compounds for drug design, as possible ligands for metal complexes, organocatalysis and also for the syntheses of heterocyclic compounds (e.g. Barbazan et al., 2008; Banerjee et al., 2009; Ghavtadze et al., 2008). As part of our ongoing studies in this area (Fun et al., 2011a,b), we now describe the structure of the title compound, (I).

The title compound, as shown in Fig. 1, exists in trans conformation with respect to the C7═N1 bond [C7═N1 = 1.2952 (11) Å]. An S(6) ring is formed via an intramolecular C15—H15A···F2 hydrogen bond (Table 1). The dihedral angle between the benzene rings (C1–C6 & C8–C13) is 42.09 (4)°.

In the crystal, Fig. 2, the molecules are linked into chains along [101] by C1—H1A···F1 hydrogen bonds (Table 1).

Experimental

Equimolar amount of [2,3-dichloro-6-methyl-5-(trifluoromethyl)phenyl]hydrazine and acetophenone were dissolved in a minimum amount of ethanol, then followed by the addition of 0.5 ml concentrated sulfuric acid. The solution was refluxed for 8 h then cooled to room temperature and poured into ice cold water. The solid product was collected through filtration and then dried using a drying oven at 80°C. The product was redissolved in ethanol for recrystalliziation to give yellow blocks of (I). Melting point: 368 K.