N-(2 0 -R-Phenyl)-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboximides with R ¼ Me (1), OMe (2), OEt (3) and H (4) were investigated. The crystal and molecular structures of 1-3, determined by single crystal methods, show different conformations of the N-(2 0 -R-phenyl) group. Anti conformations and weak intermolecular CH/p contacts were found in 2 and 3, while anti and syn conformations coexist in 1 with CH/p contacts being absent. Solid-state 13 C CP/MAS spectra confirm the X-ray molecular structural data. Two crystallographically independent molecules in the unit cell of 2 correspond to two isotropic chemical shifts for C atoms in the CP/MAS spectrum. The different molecular dynamics of both molecules in the crystal lattice of 2 indicated by the thermal factors and intermolecular CH/p contacts were clearly visible in different crosspolarisation profiles. The NMR data of 4 suggest that the phenyl ring bonded to the nitrogen is nearly coplanar to the ethanocarboximide ring. Full assignment of liquid state 1 H and 13 C NMR spectra of 1-4 was possible by application of high field NMR spectroscopy. Some incorrect assignments of 13 C chemical shifts in the literature were revised. The different ratios of [syn]: [anti] in solutions of chloroform and DMSO are explained in terms of different intermolecular CH/p interactions.y Electronic supplementary information (ESI) available: figures of the conformations in compound 1 and the molecular packing and intermolecular CH/p interactions in compounds 2 and 3. See

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