Abstract
The centrosymmetric crystal structure of the title compound, C11H16N2Se, is built up from alternating strands of (R,R)- and (S,S)-enanti-omers. These strands, which propagate along the c-axis direction, are composed of homochiral mol-ecules related to each other by twofold screw axes. The shape of the mol-ecule is an almost planar unit around the selena-diazole ring with a hexa-methyl-ene chain as an arched handle.
Highlights
The centrosymmetric crystal structure of the title compound, C11H16N2Se, is built up from alternating strands of (R,R)- and (S,S)-enantiomers. These strands, which propagate along the c-axis direction, are composed of homochiral molecules related to each other by twofold screw axes
Though the carbocyclic part is of medium ring size, the hexamethylene tether appears to be free of Pitzer and Prelog strain
No directional interactions beyond normal van der Waals contacts could be identified in the crystal
Summary
1,2,3-Selenadiazoles are synthesized from SeO2-oxidation of semicarbazones (Yalpani et al, 1971; Al-Smadi & Ratrout, 2004) and are important intermediates for the synthesis of medium-sized (Meier, 1972), heterocyclic (Detert, 2011), and strained cycloalkynes (Bissinger et al 1988). The arbitrarily chosen asymmetric molecule of the title compound (Fig. 1) has S configurations for atoms C5 and C6 but crystal symmetry generates a racemic mixture. Though the carbocyclic part is of medium ring size, the hexamethylene tether appears to be free of Pitzer and Prelog strain. The packing consists of strands of homochiral molecules, related to each other by twofold screw axes, propagating along the c-axis direction. The (R,R)- and (S,S)enantiomers alternate along the a-axis direction, being related by crystallographic c-glides (Fig. 2)
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