Four-layered [3.3]metacyclophane with ethenetetracarbonitrile

Abstract

The title complex C42H48·2C6N4 {systematic name: heptacyclo[21.13.1.15,19.16,18.110,14.124,36.128,32]dotetraconta-1(37),5(40),6(41),10(42),11,13,18,23,28,30,32(39),36(38)-dodecaene–ethenetetracarbonitrile (1/2)}, consisting of four-layered [3.3]metacyclophane (MCP) with two tetracyanoethylene (TCNE) molecules, was grown from a mixture of MCP and TCNE in chloroform solution. The four-layered [3.3]MCP has an S-shaped structure in which three [3.3]MCP moieties take syn-(chair-boat), anti-(chair-boat) and syn-(chair-boat) conformations. The two outer [3.3]MCP moieties with syn geometry contain benzene rings with a tilt of 32.95 (7)°. The central [3.3]MCP moiety has an anti geometry, in which the two benzene rings are oriented parallel to each other at a transannular distance of 2.31 Å. The TCNE molecules are stacked on either side of the outer [3.3]MCP units at a distance of 3.19 Å on one side and 3.24 Å on the other, and showed 0.80:0.20 and 0.44:0.56 disorder, respectively.