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X-ray Structural Investigation of 4-Phenyl-, 4-(o-Tolyl)- and 4-(2',4',6'-Trimethylphenyl)[2.2] paracyclophanes

Kuś P.

Polish Journal of Chemistry

2001

Vol. 75, nr 9

1351-1360

Crystal structures of 4-phenyl[2.2]paracyclophane (1), C22H20, monoclinic, P21/c, a = 14.7168(3), b = 7.8504(1), c = 15.1773(3) A, _ = 118.100(1), Z = 4; 4-(o-tolyl)[ 2.2]paracyclophane (3), C23H22, monoclinic, Cc, a = 11.354(1), b = 22.960(2), c = 7.7156(7)A, _ = 128.824(1), Z = 4; and 4-(2_,4_,6_-trimethylphenyl)[2.2]paracyclophane (6), C25H26, orthorhombic, Pbca, a = 12.892(4), b = 8.091(2), c = 35.895(9) A, _ = 90, Z = 8 have been determined. The interplanar angles between the aryl substituent and the cyclophane ring, to which they are bonded, are 38.0, 50.2 and 56.9_ in 1, 3 and 6, respectively. For 3, the methyl group of the substituent points away from the cyclophanyl cavity.

X-ray structural investigation of three 4-aryl-substituted [2.2]paracyclophanes

Jones P.G., Kuś P.

Polish Journal of Chemistry

1998

Vol. 72, nr 8

1999-2008

The low-temperature crystal structures of 4-methylphenyl[2.2]paracyclophane (1), C23H22, orthorhombic, Pbca, a=12.880(2), b=7.4234(12), c=34.425(6) A, Z=8; 2,6-dimethyl-phenyl[2.2]-paracyclophane (2), C24H24, orthorhombic, P2-12-12-1, a=8,593(3), b=12.550(4), c=15.745(4) A, Z=4, and 2,4,5-trimethylphenyl[2.2]paracyclophane (3), C25H26, monoclinic, P2-1/c, a=13.737(2), b=17.883(2), c=15.230(2) A, beta= 103.423(8)degree, Z=8 (two independent molecules) have been determined. Surprisingly, only small differences from the normal paracyclophane structure were found in the three sterically hindered species; the paracyclophane rings are mutually rotated and twisted by a few degrees, and the torsion angle between paracyvlophane and aryl rings is slightly increased in 2 and 3 compared to 1.