1-Allyl-3′-phenyl-6′H-spiro[indoline-3,4′-isoxazolo[4′,5′:5,6]pyrido[2,3-d]pyrimidine]-2,5′,7′(8′H,9′H)-trione dimethyl sulfoxide monosolvate

Abstract

In the title solvated compound, C 24 H 17 N 5 O 4 ÁC 2 H 6 OS, the solvent molecule, dimethyl sulfoxide, is linked to the title molecule by an N-HÁ Á ÁO hydrogen bond. The pyridine ring adopts a twist-boat conformation. The isoxazole ring is inclined to the indoline ring system, the pyrimidine ring, and the phenyl ring by 82.31 (7), 10.41 (8) and 53.77 (10) , respectively. There is an intramolecular C-HÁ Á Á interaction present involving the phenyl ring and the indoline ring system. In the crystal, molecules are connected by two pairs of N-HÁ Á ÁO hydrogen bonds, forming chains along the b-axis direction, and enclosing R 2 2 (8) and R 2 2 (14) ring motifs. The chains are linked by C-HÁ Á ÁO and C-HÁ Á ÁN hydrogen bonds and offset -interactions, between the pyrimidine and isoxazole rings of inversion-related molecules [centroid-centroid distance = 3.7140 (9) Å ], forming a three-dimensional structure. Structure descriptionPyrrolidine derivatives are used as norepinephrine reuptake inhibitors and 5-HT(1A) partial agonists for treating neuropsychiatric disorders including depression and anxiety (Pettersson et al., 2011). These derivatives are also used as -mannosidase inhibitors and have antitumor activities against hematological and solid malignancies (Bello et al., 2010). In view of their importance, we have undertaken the synthesis and crystal structure determination of the title compound and the results are presented herein.The molecular structure of the title compound is illustrated in Fig. 1. The solvent molecule is attached to the title molecule via an N4-H4AÁ Á ÁO5 hydrogen bond and there is an intramolecular C-HÁ Á Á interaction present involving the phenyl ring (C1-C6) and the indoline (N5/C13/C15-C21) ring system ( Fig. 1 and Table 1). The sum of the