Abstract
The title compounds, C23H16S, (I), and C26H16S, (II), are benzo-thio-phene derivatives in which the benzo-thio-phene moiety is fused with a naphthalene ring system in (I), and with an anthracene ring system in (II). In (I), the mean plane of the benzo-thio-phene ring system makes a dihedral angle of 2.28 (6)° with the naphthalene ring system, and a dihedral angle of 1.28 (6)° with the anthracene ring system in (II), showing that the fused units are essentially planar. In (I), the 4-methyl-benzene ring substituent makes a dihedral angle of 71.40 (9)° with the naphthalene ring system, while the phenyl ring substituent in (II) makes a dihedral angle of 67.08 (12)° with the anthracene ring system. In the crystals of both compounds, mol-ecules are linked by C-H⋯π inter-actions, leading to the formation of slabs parallel to (001) in (I) and to zigzag chains along [001] in (II). There are also offset π-π inter-actions present within the slabs in (I). In the crystal of (II), they link the chains, forming sheets parallel to (010). The triclinic polymorph of compound (II) has been reported [Sivasakthikumaran et al., (2012 ▸). J. Org. Chem.77, 9053-9071].
Highlights
4-methylbenzene ring substituent makes a dihedral angle of 71.40 (9) with the naphthalene ring system, while the phenyl ring substituent in (II) makes a dihedral angle of 67.08 (12) with the anthracene ring system
One of the most important drugs based on the benzothiophene system is Raloxifine, used for the prevention and treatment of osteoporosis in postmenopausal women (Jordan, 2003)
Benzothiophenes are present in luminescent components used in organic materials (Russell & Press, 1996)
Summary
The thiophene nucleus has been shown to be an important heterocyclic unit in compounds possessing promising pharmacological characteristics, such as anti-HIV PR inhibitors (Bonini et al, 2005) and anti-breast cancer (Brault et al, 2005). Benzothiophenes are present in luminescent components used in organic materials (Russell & Press, 1996). Naphtho[2,3-b]thiophene derivatives have been found to exhibit antiproliferative activity related to the inhibition of tublin polymerization (Zuse et al, 2007, 2006). As a result of their outstanding electronic testability and considerable chemical and environmental stability, thiophene derivatives have been widely used in solar cells (Justin Thomas et al, 2008; Hänsel et al, 2003), organic light-emitting diodes (OLEDs). (Zhan et al, 2007) and as NLO devices (Bedworth et al, 1996; Raposo et al, 2011).Against this background, we describe the syntheses and crystal structures of the title benzothiophene derivatives. In the triclinic polymorph of compound (II) (Sivasakthikumaran et al, 2012), the major component of the disordered phenyl ring substituent makes a dihedral angle of 79.39 (12).
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