Acta Crystallographica Section B

Structural Science

Volume 57, Part 6 (December 2001)

Acta Cryst. (2001). B57, 780-790 [doi:10.1107/S0108768101013817]

Influence of aromatic sulfonation on the geometry of [2.2]paracyclophane: crystal structures of one sulfonate, one disulfonic anhydride and five disulfonimides

D. J. A. De Ridder, K. Goubitz, M. Fontijn, P. Capková, E. Dova and H. Schenk

Abstract: The crystal structures of potassium [2.2]paracyclophane-4-sulfonate (1), [2.2]paracyclophane-4,15-disulfonic anhydride (2), [2.2]paracyclophane-4,15-disulfonimide (3), N-n-propyl-[2.2]paracyclophane-4,15-disulfonimide (4), N-isopropyl-[2.2]paracyclophane-4,15-disulfonimide (5), N-cyclopropyl-[2.2]paracyclophane-4,15-disulfonimide (6) and N-phenyl-[2.2]paracyclophane-4,15-disulfonimide (7) were established by single-crystal X-ray diffraction. The structural changes caused by sulfonation are discussed with respect to the parent [2.2]paracyclophane (tricyclo[8.2.2.2^4,7]hexadeca-4,6,10,12,13,15-hexaene). The main features are a change in the non-bonding distances between the para-phenylene rings and a rotation of these rings with respect to the molecular symmetry plane. The rings are rotated away from each other in the case of monosulfonation (1), but are rotated in the opposite way in the case of the disulfonic anhydride (2) or the disulfonimide compounds (3)-(7). The results are also discussed in terms of the parameters proposed by Keehn [(1983), Organic Chemistry, A Series of Monographs 45, edited by P. H. Keehn & S. M. Rosenfeld, Vol. 1, pp. 69-238. New York: Academic Press] showing that (bonded and non-bonded) angles involving the para-phenylene rings are mainly affected.

Online 29 November 2001


	Structure factor file (CIF format) (79.9 kbytes) Contains datablock PCF1

	Structure factor file (CIF format) (71.5 kbytes) Contains datablock PCF2

	Structure factor file (CIF format) (61.0 kbytes) Contains datablock PCF3

	Structure factor file (CIF format) (24.5 kbytes) Contains datablock PCF4

	Structure factor file (CIF format) (96.7 kbytes) Contains datablock PCF5

	Structure factor file (CIF format) (93.7 kbytes) Contains datablock PCF6

	Structure factor file (CIF format) (54.4 kbytes) Contains datablock PCF7

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