Structures of two crown-ether derivatives of 9-acridone

Abstract

(I) N-Methyl-2,5,8,11,14,17,20-heptaoxa-25-azatetracyclo[19.7.5.0(24,32),0(26,30)]tritriaconta-1 (29),-21(33),22,24(32),26(30),27-hexaen-31-one trihydrate, C26H33NO8.3H2O, M(r) = 541.6, triclinic, P1BAR, a = 7.389 (1), b = 13.255 (1), c = 14.448 (2) angstrom, alpha = 88.60 (1), beta = 78.58 (1), gamma = 81.48 (1)-degrees, V = 1371.7 (2) angstrom 3, Z = 2, D(x) = 1.31 g cm-3, lambda(Cu K-alpha) = 1.54178 angstrom, mu = 8.68 cm-1, F(000) = 580, T = 291 K, R = 0.047 for 3376 observed reflections. (II) N-Methyl-2,5,8,11,14,17-hexaoxa-22-azatetracylco[16.7.5.0.(21,29).0(23,27)]triaconta-1 (26), 18(30), 19,-21(29),23(27),24-hexaen-28-one, C24H29NO7, M(r) = 443.5, triclinic, P1BAR, a = 8.426 (2), b = 11.420 (2), c = 11.739 (4) angstrom, alpha = 87.20 (3), beta = 79.33 (3), gamma = 77.88 (2)-degrees, V = 1085.3 (5) angstrom 3, Z = 2, D(x) = 1.36 g cm-3, lambda(Mo K-alpha) = 0.71069 angstrom, mu = 1.08 cm-1, F(000) = 472, T = 291 K, R = 0.039 for 3229 observed reflections. In these substituted acridone derivatives one molecule contains both a crown ether moiety with its complexing capabilities and a heterocyclic N atom able to modify these properties. In the two compounds, the crown ether chain is nearly perpendicular to the acridinic skeleton which is planar. In (I) the water molecules take part in hydrogen bonds with the crown ether [O37...O11 = 3.03 (1), O35...O36 = 2.81 (1) angstrom] and with each other [O36...O37 = 2.93 (1), O38...O36 = 2.84 (1), O38...O37 (x + 1, y, z) = 2.89 (1) and O38...O37 (1 - x, 1 - y, 1 - z) = 2.88 (1) angstrom]. The bond lengths suggest partial localization of double bonds in the benzene rings.