Synthesis, Crystal Structure and ab initio Studies of Cyclohexyl N-Phenylcarbamate

Abstract

Cyclohexyl N-phenylcarbamate, C13H17NO2 (I), which is a useful target for biotransformations by fungi, has been synthesized and the structure has been solved by X-ray diffraction. The crystals are triclinic, space group P $$ \bar{1} $$ , with a = 5.2581 (2) A, b = 9.5080 (3) A, c = 12.6165 (4) A, α = 70.544 (2)°, β = 89.075 (2)°, γ = 80.447 (2)°, M r = 219.28, V = 585.96 (3) A3, Z = 2 and R = 0.065. In the title compound the phenyl ring makes a dihedral angle of 30.68(7)° with the carbamate group The molecules are linked into infinite chains via N–H···O hydrogen bonds along the a axis. These hydrogen-bonded chains are further linked by weaker C–H···π interactions. Quantum-mechanical ab initio calculations for the free molecule reproduce well the observed bond lengths and valency angles but show that the crystal packing might be responsible for the rotation of the phenyl ring out of the carbamate plane in the solid state conformation. In cyclohexyl N-phenylcarbamate the molecules are linked into infinite chains via N–H...O hydrogen bonds along the a axis. Ab initio calculations for the free molecule show that the crystal packing might be responsible for the rotation of the phenyl ring out of the carbamate plane in the solid state conformation.