3-Bromo-2-(4-bromo-2,5-dimethoxybenzyl)-1-phenylsulfonyl-1H-indole

Abstract

In the title compound, C23H19Br2NO4S, the orientation of the phenyl­sulfon­yl substituent with respect to the indole ring system is influenced by intra­molecular C—H⋯O inter­actions. The sulfon­yl‐bound phen­yl ring is orthogonal to the indole ring system. In the crystal structure, π–π stacking inter­actions involving the indole ring system link symmetry‐related mol­ecules into dimers.

(3-Phenylsulfanyl-1-phenylsulfonyl-1H-indol-2-yl)methyl acetate

“…The mean planes of the indole ring system make a dihedral algles of 89.6 (1) and 84.5 (8)° with respect to the phenyl rings, it shows that both the phenyl rings are perpendicular with respect to the indole ring system. The S-O, S-C, and S-N distances are 1.420 (12), 1.754 (17) and 1.676 (14) Å, respectively, these are comparable as observed in similar structures (Ravishankar et al, 2005). As a result of the electron-withdrawing character of the phenylsulfonyl group, the N-Csp 2 bond lengths, viz.…”

“…For biological activities of indole derivatives, see: Singh et al (2000); Andreani et al (2001); Quetin-Leclercq (1994); Mukhopadhyay et al (1981); Taylor et al (1999); Williams et al (1993); Sivaraman et al (1996). For related structures, see: Ravishankar et al (2005); Chakkaravarthi et al (2008). For graph-set notation of hydrogen bonds, see: Bernstein et al (1995).…”

N-[(3-Phenylsulfanyl-1-phenylsulfonyl-1H-indol-2-yl)methyl]acetamide

“…The mean plane of the indole ring system makes dihedral angles of 66.5 (7) and 81.2 (6)° with respect to the phenyl rings. The S-O, S-C, and S-N distances are 1.419 (11), 1.750 (13) and 1.679 (11) Å, respectively, these are comparable as observed in similar structures (Ravishankar et al, 2005). As a result of the electron-withdrawing character of the phenylsulfonyl group, the N-Csp 2 bond lengths, viz.…”

2,2′-(Oxydimethylene)bis[3-bromo-1-(phenylsulfonyl)-1H-indole]

“…1), which passes through atom O3. The geometry of the phenylsulfonylindole system agrees with those reported for similar structures (Beddoes et al, 1986;Ravishankar et al, 2005;Senthil Kumar, Chinnakali, Ramesh et al, 2006). The indole ring system is planar, with a maximum deviation of 0.022 (2) Å for atom C2.…”