Synthesis and characterization of N-(Arylcarbamothioyl)-cyclohexanecarboxamide derivatives: the crystal structure of N-(naphthalen-1-ylcarbamothioyl)cyclohexanecarboxamide.
A number of N-(arylcarbamothioyl)cyclohexanecarboxamide derivatives (aryl substituents: phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, o-tolyl, p-tolyl, 3-methoxyphenyl, 4-methoxyphenyl and naphthalen-1yl) have been synthesized. The compounds obtained were characterized by elemental analyses, IR spectroscopy and (1)H-NMR spectroscopy. N-(naphthalen-1-ylcarbamothioyl)cyclohexanecarboxamide, H(2)L(9), was also characterized by a single crystal X-ray diffraction study. This compound, C(18)H(20)N(2)OS, crystallizes in the triclinic space group Pī, with Z = 2, and unit cell parameters a = 6.9921(14) A, b = 11.002(2) A, c = 12.381(3) A, alpha = 113.28(3) degrees, beta = 99.38(3) degrees, and gamma = 101.85(3) degrees. The cyclohexane ring adopts a chair conformation. The molecular conformation of the compound is stabilized by an intramolecular (N2-H2***O1) hydrogen bond which forms a pseudo-six-membered ring.
Ozer
Cemal Koray
CK
Department of Chemistry, Faculty of Pharmacy, Mersin University, Mersin, TR 33169, Turkey.
Arslan
Hakan
H
VanDerveer
Don
D
Külcü
Nevzat
N
D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry*; D018360:Crystallography, X-Ray; D006844:Hydrocarbons, Cyclic / Q000138:chemical synthesis / Q000737:chemistry*; D006860:Hydrogen Bonding; D008968:Molecular Conformation; D015394:Molecular Structure; D014961:X-Ray Diffraction
D000577:Amides; D006844:Hydrocarbons, Cyclic