Ethyl 6-r-(2-chlorophenyl)-2-oxo-4-phenylcyclohex-3-ene-1-t-carboxylate

Abstract

In the title mol­ecule, C21H19ClO3, the cyclo­hexene ring adopts an envelope conformation, with all substituents equatorial. The plane through its five coplanar atoms makes dihedral angles of 12.75 (14) and 74.16 (8)° with the phenyl and benzene rings, respectively. The dihedral angle between the latter two rings is 81.73 (12)°. Inter­molecular C—H⋯O hydrogen bonds and intra­molecular C—H⋯Cl contacts are found in the crystal structure; a weak C—H⋯π inter­action is also present.

1H and 13C NMR spectral study of some 3‐aryl‐5r‐aryl‐6t‐carbethoxycyclohex‐2‐enones—a study of four‐bond 1H1H couplings

“…Also the value of J 5, 6 is the characteristic of diaxial coupling. In the earlier studies,12, 13 the torsional angle for segments involving hydrogens has not been reported. From X‐ray crystallographic data we have found that in 2b the torsional angles H(4 c )C(4)C(5)H(5), H(4 t )C(4)C(5)H(5) and H(5)C(5)C(6)H(6) are − 56.05, 173.66 and 177.86°, respectively.…”

“…For 2a–2f the experimental values of elemental analysis are in good agreement with those calculated for the molecular formulae. The structures of 2b and 2g have been determined using X‐ray crystallography 12, 13…”

“…X‐ray crystallographic studies12, 13 have shown in 2b and 2g that the torsional angles about C(1)C(2) and C(2)C(3) bonds are in the range 0.3–3.8°. Since m ‐ or p ‐substituents cannot have a significant effect on the ring torsional angles in compounds 2a–2i the torsional angles about C(1)C(2) and C(2)C(3) bonds should be in this range.…”

“…In such a conformation, the chlorine atom can interact with the CH(4 c ) and CH(5) bonds so that H‐4 c and H‐5 get partial positive charge, whereas C‐4 and C‐5 get partial negative charge. Interestingly, X‐ray crystallographic study12 has shown that in 2b the o ‐chlorophenyl group adopts such a conformation.…”

(1RS,6SR)-Ethyl 4-(4-chlorophenyl)-6-(4-fluorophenyl)-2-oxocyclohex-3-ene-1-carboxylate toluene hemisolvate

“…For asymmetry parameters, see: Duax & Norton (1975). For similar structures, see: in Anuradha et al (2009);Fun et al (2008Fun et al ( , 2009Fun et al ( , 2010; Badshah et al (2009). For a description of the Cambridge Structural Database, see: Allen (2002 Table 1 Hydrogen-bond geometry (Å , ).…”