(R*)-1-Benzyl-3-(2-hydroxyphenyl)indoline-2-one

Abstract

The title compound, C 21 H 17 NO 2 , crystallizes with two independent molecules (A and B) in the asymmetric unit. The indoline ring system is almost planar in both molecules (r.m.s. deviations = 0.020 and 0.024 Å for molecules A and B, respectively). The benzyl and phenol rings are inclined to the indole ring system by 80.39 (12) and 68.39 (12) in molecule A, and by 79.90 (13) and 74.88 (10) in molecule B. The aryl rings are inclined to one another by 33.30 (14) and 30.62 (14) in molecules A and B, respectively. In the crystal, A molecules are linked by pairs of O-HÁ Á ÁO hydrogen bonds, forming inversion dimers. The same situation is observed for the B molecules and both sets of inversion dimers enclose R 2 2 (14) ring motifs. These dimers stack along the a-axis direction and are linked by offset -interactions [intercentroid distance = 3.6802 (13) Å ] involving A and B indole ring systems, forming layers parallel to the ab plane. Structure descriptionIsatin is a starting material for the synthesis of a number of organic compounds (Hajare & Chavan, 2014). Isatin and its metabolites are constituents of many natural substances (Medvedev et al., 2007). It is found in humans and acts as a metabolic derivative of adrenaline (Sonawane & Tripathi, 2013). It exhibits endogamous activity in mammals (Chaudhary et al., 2013) and has shown cardioinhibitory effects on a frog's heart, and hypotensive, respiratory depression and antidiuretic effects (Pandeya et al., 2005). data reportsThe title compound, crystallizes with two independent molecules (A and B) in the asymmetric unit (Fig. 1). The indoline ring system is nearly planar in both molecules, the largest deviation from the mean plane being 0.042 (2) Å for atom C7 in molecule A and 0.080 (2) Å for atom O3 in molecule B. The dihedral angle between the isatin group and the phenol and benzyl rings are, respectively, 68.39 (12) and 80.39 (12) for molecule A and 74.88 (10) and 79.90 (13) for molecule B. The dihedral angle between the aryl rings is 33.30 (14) for molecule A and 30.62 (14) for molecule B. In the crystal, the A molecules are linked by pairs of O-HÁ Á ÁO hydrogen bonds, forming A-A inversion dimers. Likewise, the B molecules are also linked by a pair of O-HÁ Á ÁO hydrogen bonds, forming B-B inversion dimers (see Table 1 and Fig. 2). Both dimers enclose R 2 2 (14) ring motifs. These dimers stack along the a-axis direction and are linked by offset -interactions, involving A and B indole ring systems (Fig. 3), forming layers parallel to the ab plane [Cg1Á Á ÁCg2 i = 3.743 (1) Å , interplanar distance = 3.557 (1) Å , Cg1 and Cg2 are the centroids of the indole rings N1/C5-C8 and N2/C26-C29, respectively; symmetry code: (i) x, y, z]. Table 1 Hydrogen-bond geometry (Å , ). Symmetry codes: (i) Àx; Ày þ 2; Àz þ 1; (ii) Àx þ 1; Ày þ 1; Àz þ 1. Figure 2A partial view along the a axis of the crystal packing of the title compound, showing the formation of the O-HÁ Á ÁO hydrogen-bonded A-A (blue) and B-B (red) inversion dimers (see Table 1; hydrogen bonds are shown as...