2-Chloro-N-[4-(3-methyl-3-phenyl­cyclo­but­yl)-1,3-thia­zol-2-yl]-N′-(naphthalen-1-yl­methyl­idene)acetohydrazide

Ersin Inkaya; Muharrem Dinçer; Alaaddin Çukurovalı; Engin Yılmaz

doi:10.1107/S1600536811000183

. 2011 Jan 8;67(Pt 2):o310. doi: 10.1107/S1600536811000183

2-Chloro-N-[4-(3-methyl-3-phenylcyclobutyl)-1,3-thiazol-2-yl]-N′-(naphthalen-1-ylmethylidene)acetohydrazide

Ersin Inkaya ^a,^*, Muharrem Dinçer ^a, Alaaddin Çukurovalı ^b, Engin Yılmaz ^c

PMCID: PMC3051444 PMID: 21522998

Abstract

In the molecular structure of the title hydrazide derivative, C₂₇H₂₄ClN₃OS, the acetohydrazide group is approximately planar, with a maximum deviation of 0.017 (3) Å. The dihedral angle between the naphthylene system and the phenyl ring is 78.91 (18)°. The crystal structure is stabilized by one weak intermolecular C—H⋯O hydrogen bond and two aliphatic C—H⋯π hydrogen-bonding associations.

Related literature

For the applications and bioactivity of hydrazide derivatives, see: Feng et al. (2006 ▶); Yang et al. (2007 ▶); Kamal et al. (2007 ▶); Masunari & Tavares (2007 ▶); Rando et al. (2002 ▶). For bond-length data, see: Demir et al. (2006 ▶).

Experimental

Crystal data

C₂₇H₂₄ClN₃OS
M _r = 474.00
Monoclinic,
a = 7.498 (5) Å
b = 12.823 (5) Å
c = 24.924 (5) Å
β = 92.185 (5)°
V = 2394.6 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 296 K
0.36 × 0.22 × 0.12 mm

Data collection

Stoe IPDS 2 CCD diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T _min = 0.797, T _max = 0.961
12524 measured reflections
4206 independent reflections
1375 reflections with I > 2σ(I)
R _int = 0.135

Refinement

R[F ² > 2σ(F ²)] = 0.069
wR(F ²) = 0.156
S = 0.90
4206 reflections
298 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811000183/zs2087sup1.cif

e-67-0o310-sup1.cif^{(23.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811000183/zs2087Isup2.hkl

e-67-0o310-Isup2.hkl^{(201.9KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 and Cg2 are the centroids of the C12/C13/S1/C14/N1 and C22–C27 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O1ⁱ	0.93	2.41	3.243 (7)	148
C8—H7A⋯Cg1ⁱⁱ	0.96	2.94	3.748 (3)	143
C16—H16B⋯Cg2ⁱⁱⁱ	0.97	2.93	3.740 (8)	142

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

Acknowledgments

This study was supported financially by the Research Center of Ondokuz Mayıs University (Project No. F-461).

supplementary crystallographic information

Comment

Hydrazide derivatives of various compounds are very important units in host–guest chemistry due to their special arrangement of donor-acceptor functional groups (Feng et al., 2006; Yang et al., 2007). Hydrazine derivatives have also been associated with remarkable anticancer (Kamal et al., 2007), antibacterial (Masunari & Tavares, 2007) and tuberculostatic (Rando et al., 2002) activities. The title compound, the hydrazide derivative C₂₇H₂₄N₃OClS (I) has been synthesized and its crystal structure is reported here.

In the structure of (I) (Fig. 1) the phenyl and thiazole rings are cis-related with respect to the cyclobutane ring. The dihedral angle between the naphthylene fragment with the thiazole and phenyl rings are 35.76 (17)° and 78.91 (18)°, respectively. The cyclobutane ring is puckered, with a dihedral angle of 25.20 (5)° between the two three-membered halves of the ring. The dihedral angle between the acetohydrazide group and the thiazole ring is 32.28 (38)°. The C═O bond distance is 1.190 (6) Å comparing with a literature value of 1.187 (16) Å (Demir et al., 2006).

The crystal packing involves a weak intermolecular thiazole C13—H···O1 hydrogen bond (Table 1, Fig. 2) and intermoleculer C8—H···π (thiazole ring C12/C13/S1/C14/N1), C16—H···π (ring C22—C27) hydrogen-bonding associations (Fig. 3).

Experimental

The synthesis of the title compound was simply carried out in the following reaction (Fig. 4). A solution of 0.3975 gram (1 mmol) of N-[4-(3-methyl-3-phenyl-cyclobutyl)-thiazol-2-yl]-N-naphthalen -1-ylmethylenehydrazine was dissolved in 20 ml of dioxane containing 1 mmol triethylamine. To this solution, 90 µL (1 mmol) of chloroacetyl chloride solution in 20 ml 1,4-dioxane was added dropwise over a two hour period at room temperature with stirring. Mixture was stirred two hours more and then neutralized with 5% aqueous ammonia. The compound thus precipitated was filtered, washed with copious water and crystallized from ethanol, giving brown crystals (yield, 93%).