Structure of 3-phenyl-1-oxacyclohexane-2,6-dione

Oxacyclohexane-2,6-dione (glutaric anhydride)

“…The differences in the C=O bonds lengths existing between discussed structures are similar to those observed for two independent molecules of β-chloroglutaric acid anhydride (Koer et al, 1972) and can be justified by the different intermolecular interactions, present in the crystal network. The C1-O1-C3 angle of 124.5 (2)° remains also in agreement with the numerous literature data (Koer et al, 1972;Bocelli & Grenier-Loustalot, 1982;Bertolasi et al, 1997;Qian et al, 2006). The six-membered ring of glutaric anhydride molecule adopts nearly envelope conformation, what is confirmed by the values of puckering parameters: q 2 = 0.375 (2) Å, q 3 = 0.251 (2) Å and ψ 2 = 174.5 (4)° (Cremer & Pople, 1975) for the O1/C1/C2/C3/C4/C5 ring atom sequence.…”

“…The C1=O3 and C5=O2 bond lengths of 1.197 (3) Å and 1.188 (3) Å, respectively, remain in good agreement with those C=O bond lengths observed in related compounds crystal structures (Koer et al, 1972;Bocelli & Grenier-Loustalot, 1982;Qian et al, 2006). The differences in the C=O bonds lengths existing between discussed structures are similar to those observed for two independent molecules of β-chloroglutaric acid anhydride (Koer et al, 1972) and can be justified by the different intermolecular interactions, present in the crystal network.…”

“…For related literature, see: Bertolasi et al (1997); Bocelli & Grenier-Loustalot (1982); Cremer & Pople (1975); Freer et al (1988); Koer et al (1972); Qian et al (2006); Stefanowicz (2006); Takahashi et al (2004).…”

“…1) and some of its derivatives are commonly used as reagents in the organic synthesis (Freer et al, 1988;Takahashi et al, 2004). Several papers concerning the crystal state studies of glutaric anhydride derivatives, as 3-phenyl-1-oxacyclohexane-2,6-dione or β-chloroglutaric acid anhydride are available in the literature (Koer et al, 1972;Bocelli & Grenier-Loustalot, 1982), but surprisingly the crystal structure of the glutaric anhydride has not been determined yet.…”