Abstract

The asymmetric unit of the title compound, C12H12Cl4O2, contains two crystallographically independent mol-ecules with almost identical conformations (r.m.s. overlay fit for the non-hydrogen atoms = 0.059 Å). In each mol-ecule, the central eight-membered ring has a distorted boat configuration, and two non-planar four-membered rings are fused on either side of the eight-membered ring. A weak C-H⋯O hydrogen bond links the two independent mol-ecules. In the crystal, weak C-H⋯O hydrogen bonds link the mol-ecules into a two-dimensional network parallel to (001).

Highlights

  • The asymmetric unit of the title compound, C12H12Cl4O2, contains two crystallographically independent molecules with almost identical conformations (r.m.s. overlay fit for the non-hydrogen atoms = 0.059 Å)

  • The central eight-membered ring has a distorted boat configuration, and two nonplanar four-membered rings are fused on either side of the eight-membered ring

  • Each molecule consists of a central non-planar eight-membered cyclooctadiene [B (C2–C5/C8–C11) and E

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Summary

Chemical context

Supporting information: this article has supporting information at journals.iucr.org/e. The eight-membered-ring cyclic hydrocarbon, 1,5-cyclooctadiene (COD), attracts the attention of researchers because of its use as an intermediate product in the production of epoxides, suberic acid (1,8-octanodioic acid), caprylolactam (8-aminooctanoic acid lactam) and related chemicals and polymers COD serves as a useful precursor in the syntheses of other organic compounds and as a ligand in organometallic chemistry (Shriver & Atkins, 1999). Ketenes, containing R and R0 groups (where R, R0 can be hydrogen), and formed cumulene enon systems are reactive compounds. The stability or reactivity of ketenes depends on the electronic structures of the R and R0 groups. Ketenes providing electron-donating (+I or +M) R groups are stable, and their reactivity is low. Electron-attracting ketenes [containing (-I or -M) R groups] are less stable and behave in a more unstable manner in reactions

Structural commentary
Supramolecular features
Synthesis and crystallization
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