Crystal structure of 3′′′-(2,6-dichlorophenyl)-1′-methyl-4′,4′′′-bis(4- chlorophenyl)-4′′′,5′′′-dihydroindole-3-spiro-2′-pyrrolidine-3′-spiro-1′- cyclopentane-3″-spiro-5′′′-[1,2]oxazole-2(3H),2″-dione hemihydrate, C36H27Cl4N3O3 · 0.5H2O

Abstract

C36H28Cl4N3O3.50, orthorhombic, Iba2 (no. 45), a = 20.844(4) A, b = 27.280(6) A, c = 12.031(2) A, V = 6841.1 A, Z = 8, Rgt(F) = 0.073, wRref(F) = 0.212, T = 113 K. Source of material A mixture of 1-N-methyl-spiro[2.3']oxindole-spiro[3.2'']5''-(4chloro)benzylidenecyclopentanone-4-(4-chloro)phenylpyrrolidine (1 mmol), isatin (1 mmol) and sarcosine (1 mmol) was refluxed in methanol (60 ml) until the disappearence of the starting material as evidenced by the TLC. After the reaction was over, the solvent was removed in vacuo and the residue was treated by column chromatography (silica gel, petroleum ether/ ethylacetate, 5:1) to give the title compound. 20 mg of the title compound was dissolved in 15 ml methanol/water mixture. The solution was kept at room temperature for 15 d by natural evaporation to give colorless single crystals suitable for X-ray diffraction analysis. Experimental details The H atoms bound to C were included in the riding model approximation with d(C—H) = 0.95 0.99 A and Uiso(H) = 1.2 Ueq(C). H2Abound toNwas found in difference Fouriermap and was refinedwithUiso(H) = 1.2Ueq(N). Thewater molecule is disordered and which H atoms were not located. Discussion The molecule of title compound revealed the presence of a ring system with spiro junctions at atoms C15, C17 and C20. It consists of a 2-oxindole ring, an envelope pyrrolidine ring, an envelope isoxazoline ring and a twist-shaped cyclopentane ring. There exists a trispiro rings in the molecule which consists of a 2oxindole ring, a pyrrolidine ring, an isoxazoline ring and a cyclopentane ring. The pyrrolidine ring (N3/C20/C17/C30/C29) has an envelope conformation. C20/C17/C30/C29 part is nearly planar with the mean deviation from this plane is 0.01345(3)A. The N3 lies 0.5845(3) A from the C20/C17/C30/C29 plane in pyrrolidine ring, forming the flap of the envelope. The dihedral angle between the C20/N3/C29 plane and the C20/C17/C30/C29 mean plane is 42.7(4)°. The dihedral angle between phenyl plane (C31/C32/C33/C34/C35/C36) and C20/C17/C30/C29 plane is 98.6(3)°. In 2-oxindole ring (N2/C26/C25/C24/C23/C22/C21/ C27), the N2/C26/C25/C24/C23/C22/C21 part is nearly planar with the mean deviation from this plane of 0.0384(3)A. The C27 lies 0.2390(3)A from theN2/C26/C25/C24/C23/C22/C21 plane. The dihedral angle between N2/C26/C25/C24/C23/C22/C21 mean plane and C20/C17/C30/C29 plane in pyrrolidine ring is 86.3(3)°. The isoxazoline ring (O1/N1/C7/C8/C15)) was also an envelope conformation. O1/N1/C7/C8 form nearly a plane with mean deviation from this plane of 0.0007(3) A. The C15 lies 0.3065(3) A from the O1/N1/C7/C8 plane in isoxazoline ring, forming the flap of the envelope. The dihedral angle between the O1/N1/C7/C8 plane and the phenyl plane (C9/C10/C11/C12/ C13/C14) is 94.5(4)°. 34 Z. Kristallogr. NCS 225 (2010) 34-36 / DOI 10.1524/ncrs.2010.0013 © by Oldenbourg Wissenschaftsverlag, Munchen Crystal: colorless plate, size 0.06 × 0.12 × 0.16 mm Wavelength: Mo K+ radiation (0.71073 A) .: 3.88 cm−1 Diffractometer, scan mode: RIGAKU SATURN CCD , #\% 2,max: 50° N(hkl)measured, N(hkl)unique: 22901, 5525 Criterion for Iobs, N(hkl)gt: Iobs > 2 ((Iobs), 5024 N(param)refined: 474 Programs: SHELXS-97 [1], SHELXL-97 [2], SHELXTL [3] Table 1. Data collection and handling.