N-(3,4-Dichlorophenyl)-3-oxobutanamide

In the title compound. C10H9Cl2NO2, the acetamide residue is twisted out of the phenyl ring plane by 25.40 (9)°. An intramolecular C—H⋯O close contact is observed. The N atom of the butanamide unit forms an intermolecular N—H⋯O hydrogen bond with the symmetry-related carbonyl O atom, interlinking molecules into a C(4) chain along [100]. Additional C—H⋯O intermolecular interactions and Cl⋯Cl contacts [3.4364 (8) Å] contribute to the stability of the crystal packing.

[1]  G. Sheldrick A short history of SHELX. , 2008, Acta crystallographica. Section A, Foundations of crystallography.

[2]  A. Whitaker 583 pigment yellow GG, a mixed crystal of α‐(4‐chloro‐2‐nitrophenylhydrazono)acetoacetanilide (CI pigment yellow 6) and α‐(2‐nitrophenylhydrazono)acetoacetanilide (α‐CI pigment yellow 5) , 1986 .

[3]  Carrie J. Brown,et al.  α-(4-Methyl-2-nitrophenylhydrazono)acetoacetanilide, C17H16N4O4 , 1984 .

[4]  Warren J. Hehre,et al.  AB INITIO Molecular Orbital Theory , 1986 .

[5]  G. Richards Molecular orbital theory , 1976, Nature.

[6]  A. Becke,et al.  Density-functional exchange-energy approximation with correct asymptotic behavior. , 1988, Physical review. A, General physics.

[7]  A. Becke Density-functional thermochemistry. III. The role of exact exchange , 1993 .

[8]  N. Walker,et al.  CI Pigment Yellow 74, a-(2-methoxy-4-nitrophenylhydrazono)-a-aceto-2'-methoxyacetanilide , 1987 .

[9]  H. Lang,et al.  N‐[4‐(Pyrrolidin‐1‐ylcarbonyl­meth­oxy)phen­yl]acetamide , 2005 .

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

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

[12]  Wanyi Liu,et al.  2‐Acetyl‐3′‐chloro­acetanilide , 2005 .

[13]  A. Whitaker CI pigment yellow 65, α-(4-methoxy-2-nitrophenylhydrazono)-α-aceto-2'-methoxyacetanilide , 1987 .

[14]  Frank E. Harris,et al.  Molecular Orbital Theory , 1967 .

[15]  A. Whitaker CI Pigment Yellow 60, 4‐(2‐chlorophenylhydrazono)‐3‐methyl‐1‐phenyl‐5‐pyrazolone , 1988 .

[16]  G. Fallon,et al.  Structural, spectroscopic, and magnetic properties of mono- and bi-nuclear copper(II) complexes of N-(2-pyridinyl)ketoacetamides , 1986 .

[17]  Parr,et al.  Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. , 1988, Physical review. B, Condensed matter.