tert-Butyl 2-methyl-2-(4-nitro-benzo-yl)propanoate

Abstract

The title compound, C(15)H(19)NO(5), is bent with a dihedral angle of 61.8 (2)° between the mean planes of the benzene ring and a group encompassing the ester functionality (O=C-O-C). The dihedral angle of 0.8 (2)° between the mean planes of the nitro group and the benzene ring indicates near coplanarity. In the crystal, each mol-ecule is linked to four adjacent mol-ecules by weak C-H⋯O hydrogen-bonding inter-actions. Both benzene H atoms ortho to the ketone O atom form C-H⋯O hydrogen bonds with the keto O atoms of two neighboring mol-ecules (of the keto and ester groups, respectively), and the two other inter-actions involve the H atoms from a methyl group of the dimethyl residue, displaying C-H⋯O inter-actions with the O atoms of the nitro groups. These four inter-actions for each mol-ecule lead to the formation of two-dimensional sheets with a hydro-philic inter-ior, held together by weak hydrogen-bonded inter-actions, and a hydro-phobic exterior composed of protruding methyl groups which interst-ack with the methyl groups in adjacent sheets.

Fig. 1.

ORTEP-3 (Farrugia, 1997) drawing of the title compound with displacement ellipsoids drawn at the 50% probability level.

Fig. 2.

Labelling of the atoms for the purposes of defining the equivalent torsional angles in Table 2.

Fig. 3.

A Mercury (Macrae et al., 2008) illustration of the packing of the title compound depicting the H-bonded linkages to four adjacent molecules using blue dashed lines.

Fig. 4.

An expansion of the unit cell packing produced with Mercury (Macrae et al., 2008) depicting the nature of the weak H-bonded interactions illustrated with blue dashed lines and the relationships between non-interacting sheets looking down the c-axis.

Fig. 5.

Overlay of molecules produced with Mercury (Macrae et al., 2008) with H– (red), (Logue et al., 2010) and CH3– (blue), (Gould et al., 2010) as substituents on the para position of the phenyl ring.

Fig. 6.

Overlay of molecules produced with Mercury (Macrae et al., 2008) with H–(red), (Logue et al., 2010) and Cl–(blue), (Crosse et al., 2010) as substituents on the para position of the phenyl ring.

Fig. 7.

Overlay of molecules produced with Mercury (Macrae et al., 2008) with H–(red), (Logue et al., 2010) as the substituent on the para position of the phenyl ring and the title compound (blue).

Fig. 8.

Overlay of almost isosteric molecules produced with Mercury (Macrae et al., 2008) with CH3–(red), (Gould et al., 2010) and Cl–(blue), (Crosse et al., 2010) as substituents on the para position of the phenyl ring.

Fig. 9.

Overlay of almost isosteric molecules produced with Mercury (Macrae et al., 2008) with CH~3~–(red), (Gould et al., 2010) as the substituent on the para position of the phenyl ring and the title compound (blue).

Fig. 10.

Overlay of almost isosteric molecules produced with Mercury (Macrae et al., 2008) with Cl–(red), (Crosse et al., 2010) as the substituent on the para position of the phenyl ring and the title compound (blue).