Crystal structures of 4-methyl-2-oxo-2H-chromene-7,8-diyl diacetate and 4-methyl-2-oxo-2H-chromene-7,8-diyl bis(pent-4-ynoate)

Acta Crystallographica Section E: Crystallographic Communications

Ray J. Butcher¹  Courtney Thomas¹  Akintunde Akinyemi¹  Lystranne A. Maynard-Smith¹  Willis Marsh¹  Jerry P. Jasinski² 

[1] Department of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA;Department of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA;

关键词: crystal structure;    coumarin;    pent-4-ynoate substituent;    acetate substituent;   

DOI  :  10.1107/S2056989016005892

来源: DOAJ

【 摘 要 】

In the structures of the two title coumarin derivatives, C14H12O6, (1), and C20H16O6, (2), one with acetate and the other with pent-4-ynoate substituents, both the coumarin rings are almost planar. In (1), both acetate substituents are significantly rotated out of the coumarin plane to minimize steric repulsions. One acetate substituent is disordered over two equivalent conformations, with occupancies of 0.755 (17) and 0.245 (17). In (2), there are two pent-4-ynoate substituents, the C[triple-bond]C group of one being disordered over two positions with occupancies of 0.55 (2) and 0.45 (2). One of the pent-4-ynoate substituents is in an extended conformation, while the other is in a bent conformation. In this derivative, the planar part of both pent-4-ynoate substituents deviate from the coumarin plane. The packing of (1) is dominated by π–π stacking involving the coumarin rings and weak C—H...O contacts link the parallel stacks in the [101] direction. In contrast, in (2) the packing is dominated by R22(24) hydrogen bonds, involving the acidic sp H atom and the oxo O atom, which link the molecules into centrosymmetric dimers. The bent conformation of one of the pent-4-ynoate substituents prevents the coumarin rings from engaging in π–π stacking.

【 授权许可】

Unknown