1,3-Bis{(+)-(S)-[1-(1-naphthyl)ethyl]iminomethyl}benzene dichloromethane solvate

Abstract

In the title compound, C32H28N2·CH2Cl2, the complete Schiff base and solvent molecules are both generated by crystallographic twofold axes, with the two C atoms of the former and the C atom of the latter lying on the rotation axis. The central benzene ring is substituted with two chiral groups including imine functionalities, with the common E configuration. The dihedral angle between the central benzene ring and the terminal naphthalene ring is 45.42 (9)° and that between the two naphthalene rings is 89.16 (8)°. The conformation of the Schiff base allows solvent mol­ecules to fill the voids in the crystal, affording a stable 1:1 solvate, but the solvent inter­acts poorly with the Schiff base, as reflected by its rather high displacement parameters.

1,4-Bis{(+)-(S)-[1-(1-naphthyl)ethyl]iminomethyl}benzene

“…Although no π-π contacts contribute to the stabilization of the crystal structure, the molecules are efficiently packed along the short [100] axis in the crystal. As a consequence, no voids are available for lattice solvent insertion, a situation contrasting with that observed for an isomeric system previously described (Espinosa Leija et al, 2009): for the meta-substituted molecule, a 1:1 solvate was crystallized with CH 2 Cl 2 , with solvent molecules filling large voids generated by the molecular conformation.…”

“…For solvent-free synthesis in organic chemistry, see: Jeon et al (2005); Noyori (2005); Tanaka & Toda (2000); Tovar et al (2007). For related chiral Schiff bases constructed from a bissubstituted benzene core, see: Allouchi et al (1994); Hamaker & Oberts (2006); Espinosa Leija et al (2009). For the use of the enantiomer of the title compound as a chiral dopant for liquid crystals, see: Watanabe & Fukuda (2008).…”

“…These compounds are particularly interesting since they can potentially act in a variety of coordination modes. Continuing our work on the synthesis and characterization of this kind of compounds (Tovar et al, 2007;Espinosa Leija et al, 2009), we synthesized the title compound under solvent-free conditions and report herein its crystal structure.…”

2,5-Bis{[(−)-(S)-1-(4-bromophenyl)ethyl]iminomethyl}thiophene

“…For the solvent-free organic synthesis, see: Tanaka & Toda (2000). For the structure of a chiral bis-aldimine compound, see: Espinosa Leija et al (2009). For structures of thiophenes substituted in positions 2 and 5 by imine functionalities, see: Bernè s et al (2013); Kudyakova et al (2012).…”

“…Absolute structure: Flack (1983), 914 Friedel pairs Absolute structure parameter: 0.011 8Data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2013); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012). In continuation of our work focused on chiral bisimines (Espinosa Leija et al, 2009;Bernès et al, 2013), we have now synthesized the title compound under the solvent-free approach because of the cleaner, safer, and easier aspects to perform in the synthetic work. So, solvent-free conditions are becoming more popular and it is often claimed that the best solvent is no solvent.…”