Synthesis, structure and Hirshfeld surface analysis of 2-oxo-2 H-chromen-6-yl 4- tert-butyl-benzoate: work carried out as part of the AFRAMED project

Abstract

In the title compound, C₂₀H₁₈O₄, the dihedral angle between the 2H-chromen-2-one ring system and the phenyl ring is 89.12 (5)°. In the crystal, the mol-ecules are connected through C-H⋯O hydrogen bonds to generate [010] double chains that are reinforced by weak aromatic π-π stacking inter-actions. The unit-cell packing can be described as a tilted herringbone motif. The H⋯H, H⋯O/O⋯H, H⋯C/C⋯H and C⋯C contacts contribute 46.7, 24.2, 16.7 and 7.6%, respectively, to its Hirshfeld surface.

Keywords: Hirshfeld surface; coumarin derivative; crystal structure; herringbone packing.

Figure 1

The mol­ecular structure of I with displacement ellipsoids drawn at the 50% probability level.

Figure 2

Fragment of a [010] chain in the structure of I showing the hydrogen bonds involving C3, C6 and C9 as black dashed lines.

Figure 3

Partial packing diagram for I showing [010] double chains arising from C—H⋯O hydrogen bonds (black dashed lines in one chain, magenta dashed lines in the other and the C16 cross-linking bonds in blue).

Figure 4

The unit-cell packing for I viewed down [010].

Figure 5

(a) Hirshfeld surface of I mapped over d _norm and (b) two-dimensional fingerprint plots of (b) overall and delineated into contributions from different contacts: (c) H—H, (d) H—O/O—H, (e) H—C/C—H and (f) C—C.