Synthesis and structure of new bronchospasmolytic agents. I

The crystal structures of two phenylethanolamines showing bronchospasmolytic activity have been determined at room temperature [293 (2) K]. Crystal data are as follows: 11-morpholinotricyclo[6.3.0.0(2,7)]undeca-2,4,6-trien-l-ol (3), C15H19NO2, M(r) = 245.3, triclinic, P1, a = 10.360 (5), b = 12.169 (5), c = 12.488 (4) A, alpha = 95.14 (10), beta = 108.49 (12), gamma = 114.69 (5) degrees, V = 1311 (2) A3, Z = 4, Dx = 1.243 Mg m-3, Cu K alpha 1 radiation, lambda = 1.540562 A, mu = 0.618 mm-1, F(000) = 528, R = 0.0537 for 3009 observed reflections; 4-morpholino-1,2-benzocyclononen-3-ol monohydrate (5), C17H25NO2.H2O, M(r) = 293.4, monoclinic, P2(1)/c, a = 10.063 (9), b = 19.398 (5), c = 8.670 (5) A, beta = 110.56 (1) degree, V = 1585 (2) A3, Z = 4, Dx = 1.230 Mg m-3, Mo K alpha 1 radiation, lambda = 0.709300 A, mu = 0.0778 mm-1, F(000) = 640, R = 0.0376 for 1407 observed reflections. The stereochemistry of compound (3) is found to be 'all cis', which allows the mechanism of formation of these compounds to be interpreted. The various aspects of the conformations of these molecules are discussed.