Crystal structures of three 1-oxo-1,2-dihydronaphthalene derivatives: Dimethyl 4-(4-methoxyphenyl)-2-(4-methylphenyl)-1-oxo-1,2-dihydronaphthalene-2,3-dicarboxylate, dimethyl 1-oxo-2-(pyren-4-yl)-4-(thiophen-2-yl)-1,2-dihydronaphthalene-2,3-dicarboxylate and ethyl 1-oxo-2-phenyl-2,4-bis(thiophen-2-yl)-1,2-dihydronaphthalene-3-carboxylate

Abstract

In the title 1-oxo-1,2-dihydronaphthalene derivatives, C28H24O6, (I), C34H22O5S, (II), and C27H20O3S2, (III), the cyclohexa-1,3-diene rings of the 1,2-dihydronaphthalene ring systems adopt half-chair, boat and half-chair conformations, respectively. The carbonyl O atoms attached to the dihydronaphthalene ring systems are each significantly deviated from the mean plane of the 1,2-dihydronaphthalene ring system, by 0.6162(12)Å in (I), 0.6016(16)Å in (II) and 0.515(3)Å in (III). The mean planes of the 1,2-dihydronaphthalene ring systems make dihedral angles of 85.83(3), 88.19(3) and 81.67(8)°, respectively, with the methylphenyl ring in (I), the pyrene ring in (II) and the phenyl ring in (III). In (I), the molecular structure is stabilized by an intramolecular C - H⋯O hydrogen bond, generating an S(6) ring motif. In the crystal of (I), molecules are linked by an intermolecular C - H⋯O hydrogen bond, which generates a C(8) zigzag chain running along [100]. Adjacent chains are further connected by C - H⋯π and offset π-π interactions [centroid-centroid distance = 3.6572(9)Å], forming a double-chain structure. In the crystals of (II) and (III), molecules are linked into chain structures by offset π-π interactions with centroid-centroid distances of 3.5349(12) and 3.8845(13)Å for (II) and 3.588(2)Å for (III). In (II) and (III), the thiophene rings are orientationally disordered over two sites, with occupancy ratios of 0.69:0.31 for (II), and 0.528(4):0.472(4) and 0.632(5):0.368(5) for (III).