Abstract
Cyclohexyl N-phenylcarbamate, C(13)H(17)NO(2) (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 (1) over bar, with a = 5.2581 (2) angstrom, b = 9.5080 (3) angstrom, c = 12.6165 (4) angstrom, alpha = 70.544 (2)degrees, beta = 89.075 (2)degrees, gamma = 80.447 (2)A degrees, M (r) = 219.28, V = 585.96 (3) angstrom(3), Z = 2 and R = 0.065. In the title compound the phenyl ring makes a dihedral angle of 30.68(7)degrees with the carbamate group The molecules are linked into infinite chains via N-H center dot center dot center dot O hydrogen bonds along the a axis. These hydrogen-bonded chains are further linked by weaker C-H center dot center dot center dot pi 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.