Crystal structures of two triazola-dioxola-benzena-cyclo-nona-phanes.
In the title compounds, C25H29BrN5O7, (I) [systematic name: (Z)-1(5)-bromo-3(2),3(2)-dimethyl-2(1)-nitro-2(2),2(3),2(5),2(6),2(7),2(7a),3(3a),3(5),3(6),3(6a)-deca-hydro-2(1) H,6(1) H-4,9-dioxa-2(3,2)-pyrrolizina-6(4,1)-triazola-3(5,6)-furo[2,3-d][1,3]dioxola-1(1,2)-benzena-cyclo-nona-phane], and C24H29N5O7S, (II) [systematic name: (Z)-3(2),3(2)-dimethyl-2(7)-nitro-2(5),2(6),2(7),2(7a),3(3a),3(5),3(6),3(6a)-octa-hydro-2(1) H,2(3) H,6(1) H-4,9-dioxa-2(5,6)-pyrrolo-[1,2-c]thia-zola-6(4,1)-triazola-3(5,6)-furo[2,3-d][1,3]dioxola-1(1,2)-benzena-cyclo-nona-phane], the triazole rings adopt almost planar conformations. In (I), the fused pyrrolidine rings adopt envelope conformations with the C atoms opposite the fused N-C bond as the flap in each ring, and their mean planes are inclined to one another by 52.8 (3)°. In (II), the pyrrolidine and thia-zole rings are both twisted on the fused N-C bond, and their mean planes are inclined to one another by 70.8 (2)°. In both (I) and (II), the furan ring adopts an envelope conformation with the adjacent C atom of the macrocycle as the flap. In the crystal of (I), mol-ecules are linked via C-H⋯N and C-H⋯O hydrogen bonds, forming sheets parallel to (10-1), while in (II), mol-ecules are linked via C-H⋯N and C-H⋯O hydrogen bonds, forming helical chains propagating along [010], which are linked via C-H⋯S hydrogen bonds, forming slabs parallel to (001).
Centre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India.
Vijayan
V
Viswanathan
Department of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India.
Naga Siva
NS
Rao
Department of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India.
Raghavachary
R
Raghunathan
Centre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India.
Devadasan
D
Velmurugan
chiral; crystal structure; dioxalabenzena­cyclo­nona­phane; hydrogen bonding; pyrrolizine; pyrrolo­thia­zole; tetra­hydro­durodioxole; triazole