Abstract

The title compounds, C24H22O6 (I) and C24H22O6 (II), each crystallize with half a mol-ecule in the asymmetric unit. The whole mol-ecule of compound (I) is generated by twofold rotation symmetry, the twofold axis bis-ecting the central benzene ring. The whole mol-ecule of compound (II) is generated by inversion symmetry, the central benzene ring being located on an inversion center. In (I), the outer benzene rings are inclined to each other by 59.96 (10)° and by 36.74 (9)° to the central benzene ring. The corresponding dihedral angles in (II) are 0.0 and 89.87 (12)°. In the crystal of (I), mol-ecules are linked by C-H⋯O hydrogen bonds and C-H⋯π inter-actions, forming ribbons propagating along the [10] direction. In the crystal of (II), mol-ecules are linked by C-H⋯O hydrogen bonds, forming a supra-molecular framework. The Hirshfeld surface analyses indicate that for both compounds the H⋯H contacts are the most significant, followed by O⋯H/H⋯O and C⋯H/H⋯C contacts.

Highlights

  • The title compounds, C24H22O6 (I) and C24H22O6 (II), each crystallize with half a molecule in the asymmetric unit

  • The whole molecule of compound (II) is generated by inversion symmetry, the central benzene ring being located on an inversion center

  • In the crystal of (I), molecules are linked by C—HÁ Á ÁO hydrogen bonds and C—HÁ Á Á interactions, forming ribbons propagating along the [101] direction

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Summary

Chemical context

A phenolic compound, has been reported to offer neuroprotection against experimental Huntington’s disease and global ischemia by virtue of its antioxidant, anti-inflammatory and antiapoptotic properties. Vanillin is a potential future therapeutic agent by virtue of its multiple pharmacological properties relevant to the treatment of neurodegenerative diseases (Dhanalakshmi et al, 2015). Studies have revealed that the root and pod extracts of the plants Heiidesmus Indicus and vanilla planifola (plant-based food-flavouring agents) produce the fragrant phenolic compounds 2-hydroxy-4-methoxybenzaldehyde (MBALD) and 4-hydroxy-3-methoxybenzaldehyde (vanillin). These compounds have been shown to be effective in treating Alzheimer’s disease and other neurological dysfunctions (Kundu & Mitra, 2013). Symmetry codes: (i) Àx; y þ 12; Àz þ 32; (ii) x; Ày þ 32; z À 12

Structural commentary
Hirshfeld surface analysis
Database survey
Refinement
Full Text
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