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

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.

In the molecular structure of the title hydrazide derivative, C 27 H 24 ClN 3 OS, 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-HÁ Á ÁO hydrogen bond and two aliphatic C-HÁ Á Á hydrogen-bonding associations. 298 parameters H-atom parameters constrained Á max = 0.14 e Å À3 Á min = À0.16 e Å À3 Table 1 Hydrogen-bond geometry (Å , ).

D-HÁ
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.

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%).

Refinement
The data was poor because of the weakly diffracting crystals which were not of good quality. Although a long exposure time (5 minute) was applied, the reflections were quite weak, resulting in a too low observed/unique reflection ratio. H atoms were positioned geometrically and treated using a riding model, fixing the bond lengths at 0.96, 0.97, 0.98 and 0.93 Å for CH 3 , CH 2 , CH and CH(aromatic), respectively. The displacement parameters of the H atoms were constrained with U iso (H) = 1.2U eq (aromatic, methylene or methine C) or 1.5U eq (methyl C). Fig. 1. An ORTEP-3 (Farrugia, 1997) drawing of (I), showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.  Table 1.  Table 1.