Brandy Yakini, Butcher Ray J, Bakare Oladapo
Department of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA.
Acta Crystallogr Sect E Struct Rep Online. 2012 Sep 1;68(Pt 9):o2775-6. doi: 10.1107/S1600536812034150. Epub 2012 Aug 25.
The title compound, C(17)H(11)NO(3), was an inter-mediate synthesized during bis-acyl-ation of 2-amino-1,4-naphtho-quinone with benzoyl chloride. A mixture of block- and needle-shaped crystals were obtained after column chromatography. The block-shaped crystals were identified as the imide and the needles were the title amide. The naphtho-quinone scaffold is roughly planar (r.m.s. deviation = 0.047 Å for the C atoms). The N-H and C=O bonds of the amide group are anti to each other. A dihedral angle between the naphtho-quinone ring system and the amide group of 3.56 (3)°, accompanied by a dihedral angle between the amide group and the phenyl group of 9.51 (3)°, makes the naphtho-quinone ring essentially coplanar with the phenyl ring [dihedral angle = 7.12 (1)°]. In the crystal, molecules are linked by a weak N-H⋯O hydrogen bond and by two weak C-H⋯O interactions leading to the formation of zigzag chains along [010].
标题化合物C(17)H(11)NO(3)是在2-氨基-1,4-萘醌与苯甲酰氯的双酰化反应过程中合成的中间体。柱色谱后得到块状和针状晶体的混合物。块状晶体被鉴定为酰亚胺，针状晶体为标题酰胺。萘醌骨架大致呈平面状（C原子的均方根偏差 = 0.047 Å）。酰胺基团的N - H键和C = O键相互反式排列。萘醌环系与酰胺基团之间的二面角为3.56 (3)°，酰胺基团与苯基之间的二面角为9.51 (3)°，使得萘醌环与苯环基本共面 [二面角 = 7.12 (1)°]。在晶体中，分子通过弱N - H⋯O氢键和两个弱C - H⋯O相互作用连接，沿[010]方向形成锯齿链。
