Synthesis and Crystal Structure of N-phenyl-N-[(o-nitrophenylacetyl)oxy]benzamide

The compound N-phenyl-N-[(o-nitrophenylacetyl)oxy]benzamide (C21H16N2O5, M-r = 376) has been synthesized by the reaction of N-hydroxy-N-phenylbenzamide with 2-(2-nitro-phenyl)acetyl chloride in dichlorom-ethane and its structure was characterized by H-1 NMR, C-13 NMR, IR, H RMS(ESI) and single-crystal X-ray diffraction. The crystal of the title compound belongs to monoclinic, space group C2/c with a = 32.30(2), b = 8.400(5), c = 15.099(9) angstrom, beta = 114.256(10)degrees, V = 3735(4) angstrom(3), Z = 8, D-c = 1.339 g/cm(3), F(000) = 1568 mu = 0.097 mm(-1), the final R = 0.0506 and wR = 0.1176 for 2318 observed reflections (I> 2 sigma(I)). The title molecule contains three branched chains with its center placed at the midpoint of N. The phenyl ring (C(1)similar to C(6)) makes a dihedral angle of 70.3(1)degrees with the phenyl ring (C(10)similar to C(15)) of benzoyl group, and 14.3(1)degrees with the phenyl ring (C(16)similar to C(21)). Hydrogen bonds C(5)-H(5)center dot center dot center dot O(1) and C(12)-H(12)center dot center dot center dot O(3) together with pi-pi stacking interactions contribute to the stability of the structure.