Crystal structure of a four-layered [3.3](3,5)pyridinophane

Abstract

The title compound, C40H46N2 {systematic name: 12,30-diazaheptacyclo[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}, has syn–anti–syn geometry wherein the two outer [3.3]metacyclophane (MCP) moieties have a syn geometry, and contain the facing benzene and pyridine rings at dihedral angles of 26.26 (10) and 26.46 (10)°, respectively. The rings of the central [3.3]MCP unit are not parallel, but orientated at a slight angle of 2.66 (9)°. Three bridging methylene groups are disordered over two sets of sites in a 0.60:0.40 ratio. In the crystal, the molecules are linked by C—H...N interactions and intermolecular C—H...π short contacts, generating a three-dimensional network.

Keywords

• crystal structure
• metacyclophane
• pyridinophane
• transannular p-electronic interaction
• C—H...N hydrogen bond
• intermolecular short contact