Syntheses and structures of two benzoyl amides: 2-chloro-4-eth-oxy-3,5-dimeth-oxy-N-(3-oxo-cyclo-hex-1-en-1-yl)benzamide and 2-chloro-N-(5,5-dimethyl-3-oxo-cyclo-hex-1-en-1-yl)-4-eth-oxy-3,5-di-meth-oxy-benzamide.

Alan J Anderson,Edward Ollie,Ray J Butcher

doi:10.1107/s2056989021001778

Alan J Anderson, Edward Ollie + Show 1 more

Open Access

https://doi.org/10.1107/s2056989021001778

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Abstract

The first title benzoyl amide, C17H20ClNO5 (3a), crystallizes in the monoclinic space group P21/c with Z = 4 and the second, C19H24ClNO5 (3b), also crystallizes in P21/c with Z = 8 (Z' = 2), thus there are two independent mol-ecules in the asymmetric unit. In 3a, the phenyl ring makes a dihedral angle of 50.8 (3)° with the amide moiety with the C=O group on the same side of the mol-ecule as the C-Cl group. One meth-oxy group is almost in the plane of the benzene ring, while the eth-oxy and other meth-oxy substituent are arranged on opposite sides of the ring with the eth-oxy group occupying the same side of the ring as the C=O group in the amide moiety. For one of the two mol-ecules in 3b, both the amide and 5,5-dimethyl-3-oxo-cyclo-hex-1-en-1-yl moieties are disordered over two sets of sites with occupancies of 0.551 (2)/0.449 (2) with the major difference between the two conformers being due to the conformation adopted by the cyclo-hex-2-en-1-one ring. The three mol-ecules in 3b (i.e., the undisordered mol-ecule and the two disorder components) differ in the arrangement of the subsituents on the phenyl ring and the conformation adopted by their 5,5-dimethyl-3-oxo-cyclo-hex-1-en-1-yl moieties. In the crystal of 3a, N-H⋯O hydrogen bonds link the mol-ecules into a zigzag chain propagating in the [001] direction. For 3b a combination of C-H⋯O and N-H⋯O inter-molecular inter-actions link the mol-ecules into a zigzag ribbon propagating in the [001] direction.

Highlights

The first title benzoyl amide, C17H20ClNO5 (3a), crystallizes in the monoclinic space group P21/c with Z = 4 and the second, C19H24ClNO5 (3b), crystallizes in P21/c with Z = 8 (Z0 = 2), there are two independent molecules in the asymmetric unit
One methoxy group is almost in the plane of the benzene ring, while the ethoxy and other methoxy substituent are arranged on opposite sides of the ring with the ethoxy group occupying the same side of the ring as the C O group in the amide moiety
For 3b a combination of C—HÁ Á ÁO and N—HÁ Á ÁO intermolecular interactions link the molecules into a zigzag ribbon propagating in the [001] direction

Summary

Chemical context

Enaminones are compounds in which a nitrogen atom is conjugated through a carbon–carbon double bond to an ester (vinylogous urethane) or a ketone (vinylogous amide) functional group (see Scheme). For 3ba (Fig. 2) the central phenyl ring makes a dihedral angle of 54.5 (3) with the amide moiety with the C O group on the opposite side of the molecule as the C—Cl group in contrast to the situation in 3a For 3bb, the central phenyl ring makes a dihedral angle of 55.8 (9) with the amide moiety with the C O group on the opposite side of the molecule as the C—Cl group [torsion angle for C2B— C1BÁ Á ÁC11B—O4B = À122.81 (13)].

Supramolecular features

Database survey

Synthesis and crystallization

Refinement

C15 H15A H15B C16 H16A H16B C17 H17A H17B