Abstract
The syntheses and crystal structures of five 2-benzyl-idene-1-benzosuberone [1-benzosuberone is 6,7,8,9-tetra-hydro-5H-benzo[7]annulen-5-one] derivatives, viz. 2-(4-meth-oxy-benzyl-idene)-1-benzosuberone, C19H18O2, (I), 2-(4-eth-oxy-benzyl-idene)-1-benzosuberone, C20H20O2, (II), 2-(4-benzyl-benzyl-idene)-1-benzosuberone, C25H22O2, (III), 2-(4-chloro-benzyl-idene)-1-benzosuberone, C18H15ClO, (IV) and 2-(4-cyano-benzyl-idene)-1-benzosuberone, C19H15NO, (V), are described. The conformations of the benzosuberone fused six- plus seven-membered ring fragments are very similar in each case, but the dihedral angles between the fused benzene ring and the pendant benzene ring differ somewhat, with values of 23.79 (3) for (I), 24.60 (4) for (II), 33.72 (4) for (III), 29.93 (8) for (IV) and 21.81 (7)° for (V). Key features of the packing include pairwise C-H⋯O hydrogen bonds for (II) and (IV), and pairwise C-H⋯N hydrogen bonds for (V), which generate inversion dimers in each case. The packing for (I) and (III) feature C-H⋯O hydrogen bonds, which lead to [010] and [100] chains, respectively. Weak C-H⋯π inter-actions consolidate the structures and weak aromatic π-π stacking is seen in (II) [centroid-centroid separation = 3.8414 (7) Å] and (III) [3.9475 (7) Å]. A polymorph of (I) crystallized from a different solvent has been reported previously [Dimmock et al. (1999 ▸) J. Med. Chem. 42, 1358-1366] in the same space group but with a packing motif based on inversion dimers resembling that seen in (IV) in the present study. The Hirshfeld surfaces and fingerprint plots for (I) and its polymorph are com-pared and structural features of the 2-benzyl-idene-1-benzosuberone family of phases are surveyed.
Highlights
The syntheses and crystal structures of five 2-benzylidene-1-benzosuberone [1-benzosuberone is 6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one] derivatives, viz. 2-(4-methoxybenzylidene)-1-benzosuberone, C19H18O2, (I), 2-(4-ethoxybenzylidene)-1-benzosuberone, C20H20O2, (II), 2-(4-benzylbenzylidene)-1benzosuberone, C25H22O2, (III), 2-(4-chlorobenzylidene)-1-benzosuberone, C18H15ClO, (IV) and 2-(4-cyanobenzylidene)-1-benzosuberone, C19H15NO, (V), are described
The conformations of the benzosuberone fused six- plus seven-membered ring fragments are very similar in each case, but the dihedral angles between the fused benzene ring and the pendant benzene ring differ somewhat, with values of 23.79 (3) for (I), 24.60 (4) for (II), 33.72 (4) for (III), 29.93 (8) for (IV) and 21.81 (7) for (V)
The structurally related 2-benzylidenebenzocycloalkanone compounds, viz. (E)-2-benzylidene-2,3-dihydro-1H-inden-1one (n = 1), (E)-2-benzylidene-1-tetralone (n = 2) and (E)-2benzylidene-1-benzosuberone (n = 3), which differ with respect to the number of methylene groups, n, in the alkanone ring fused to the benzene ring have attracted attention in a number of areas
Summary
(E)-2-benzylidene-2,3-dihydro-1H-inden-1one (n = 1), (E)-2-benzylidene-1-tetralone (n = 2) and (E)-2benzylidene-1-benzosuberone (n = 3), which differ with respect to the number of methylene groups, n, in the alkanone ring fused to the benzene ring (see Scheme 1) have attracted attention in a number of areas. Gautam et al, 2016: Dimmock et al, 1999, 2002), antimycotic (Al-Nakib et al, 1997) and antifungal (Gupta & Jain, 2015) properties Their physical properties include nonlinear optical (Watson et al, 1993) and UV hypsochromic shifts and fluorescence effects (Fodor et al, 2011). In continuation of our earlier reports of the crystal structures and Hirshfeld surface analyses of a number of (E)-2benzylidene-2,3-dihydro-1H-inden-1-one derivatives (Baddeley et al, 2017a) and (E)-2-benzylidene-1-tetralone (Baddeley et al, 2017b), we describe the syntheses and crystal structures of 2-(4-methoxybenzylidene)-1-benzosuberone, (I), 2-(4ethoxybenzylidene)-1-benzosuberone, (II), 2-(4-benzylbenzylidene)-1-benzosuberone, (III), 2-(4-chlorobenzylidene)-1-benzosuberone, (IV), and 2-(4-cyanobenzylidene)-1-benzosuberone, (V) (see Scheme 2)
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