(E)-2-(2,6-Dichlorophenyl)-2-(phenylimino)acetamide

In the title compound, C14H10Cl2N2O, which is an important synthetic precursor of a human immunodeficiency virus type 1 (HIV-1) inhibitor, the dihedral angle between the 2,6-dichlorophenyl ring and the phenyl ring is 69.4 (1)°. In the crystal structure, the molecules form centrosymmetric dimers via N—H⋯O hydrogen bonds with an R 2 2(8) motif. The dimers are connected by intermolecular C—H⋯O and C—H⋯π interactions.

[1]  Raymond E. Davis,et al.  Patterns in Hydrogen Bonding: Functionality and Graph Set Analysis in Crystals , 1995 .

[2]  F. Allen The Cambridge Structural Database: a quarter of a million crystal structures and rising. , 2002, Acta crystallographica. Section B, Structural science.

[3]  M. Nishio CH/π hydrogen bonds in crystals , 2004 .

[4]  J. Klinowski,et al.  Crystal engineering using co-crystallisation of phenazine with dicarboxylic acids , 2000 .

[5]  Olga Kennard,et al.  Tables of bond lengths determined by X-ray and neutron diffraction. Part 1. Bond lengths in organic compounds , 1987 .

[6]  F. S. Mathews,et al.  A semi-empirical method of absorption correction , 1968 .

[7]  G. G. Stokes "J." , 1890, The New Yale Book of Quotations.

[8]  Olga Kennard,et al.  Crystallographic evidence for the existence of CH.cntdot..cntdot..cntdot.O, CH.cntdot..cntdot..cntdot.N and CH.cntdot..cntdot..cntdot.Cl hydrogen bonds , 1982 .

[9]  Robin Taylor,et al.  Mercury: visualization and analysis of crystal structures , 2006 .

[10]  J. Malone,et al.  X[mdash ]H[middot][middot][middot][pi ] (phenyl) interactions Theoretical and crystallographic observations , 1997 .

[11]  Anthony L. Spek,et al.  Journal of , 1993 .

[12]  H. L. Carrell,et al.  C-H...O hydrogen bonded multi-point recognition in molecular assemblies of dibenzylidene ketones and 1,3,5-trinitrobenzenes , 1997 .

[13]  Y. Yamashita,et al.  One-Dimensional Zigzag Chain Structures with Intermolecular C–H···π and C–H···O Interactions Consisted of Phthalic Acid and Pyridine Derivatives , 2001 .

[14]  R. Pauwels,et al.  Potent and highly selective human immunodeficiency virus type 1 (HIV-1) inhibition by a series of alpha-anilinophenylacetamide derivatives targeted at HIV-1 reverse transcriptase. , 1993, Proceedings of the National Academy of Sciences of the United States of America.