Trimethyl[3-methyl-1-(o-tolenesulfonyl)indol-2-ylmethyl]ammonium iodide and benzyl[3-bromo-1-(phenylsulfonyl)indol-2-ylmethyl]tolylamine

Abstract

The title compounds, C(20)H(25)N(2)O(2)S(+).I(-), (I), and C(29)H(25)BrN(2)O(2)S, (II), respectively, both crystallize in space group P-1. The pyrrole ring subtends an angle with the sulfonyl group of 33.6 degrees in (I) and 21.5 degrees in (II). The phenyl ring of the sulfonyl substituent makes a dihedral angle with the best plane of the indole moiety of 81.6 degrees in (I) and 67.2 degrees in (II). The lengthening or shortening of the C-N bond distances in both compounds is due to the electron-withdrawing character of the phenylsulfonyl group. The S atoms are in distorted tetrahedral configurations. The molecular structures are stabilized by C-H.O and C-H.I interactions in (I), and by C-H.O and C-H.N interactions in (II).

(Z)-2-(1-Phenylsulfonyl-1H-indol-3-ylmethylene)-1-azabicyclo[2.2.2]octan-3-one and (Z)-(S)-2-(1-phenylsulfonyl-1H-indol-3-ylmethylene)-1-azabicyclo[2.2.2]octan-3-ol

“…48 (8) ]. This type of deviation in the sulfonyl group has been reported previously and is due to the repulsive interaction between the short S O bonds (Seshadri et al, 2002). The S O, SÐC and SÐN distances are comparable to those found in N-phenylsulfonamides (Gomes et al, 1993).…”

N-{4-Bromo-2-[(3-bromo-1-phenylsulfonyl-1H-indol-2-yl)methyl]-5-methoxyphenyl}acetamide

“…The sulfonyl-bound phenyl ring is orthogonal to the indole ring system, forming a dihedral angle of 89.09 (8) . The SÐN, SÐO and SÐC distances are comparable with the values reported for related phenylsulfonylindoles (Sankaranarayanan et al, 2001;Seshadri et al, 2002) The conformation of the attachment of the benzyl substituent to the indole ring system is described by the N1ÐC1Ð C15ÐC16 torsion angle of 85.9 (3) ; the C1ÐC15ÐC16ÐC17 torsion angle of 38.6 (4) shows how the phenyl ring of the benzyl moiety is oriented. The mean plane through the acetylamido group makes a dihedral angle of 57.0 (1) with the phenyl ring of the benzyl moiety.…”

“…Atom S1 has a distorted tetrahedral con®guration, with the angles O2ÐS1ÐO1 [120.1 (2) ] and N1ÐS1ÐC9 [104.5 (1) ] deviating signi®cantly from ideal tetrahedral values. Similar distortions in the sulfonyl group have been reported and are attributed to the repulsive interaction between the short S O bonds (Sankaranarayanan et al, 2001;Seshadri et al, 2002). The conformation of the phenylsulfonyl group with respect to the indole moiety is described by the torsion angles O1ÐS1Ð N1ÐC1 [36.3 (3) ], O2ÐS1ÐN1ÐC8 [À35.2 (3) ] and N1Ð S1ÐC9ÐC10 [116.1 (3) ].…”

(Z)-2-[1-(4-Methylphenylsulfonyl)-1H-indol-3-ylmethylene]-1-azabicyclo[2.2.2]octan-3-one

“…The indole ring system is planar with bond distances and angles comparable with those previously reported for other indole derivatives (Mason et al, 2003). This observation is in agreement with previously reported values for the sulfonyl group, and is due to the repulsive interaction between the short S O bonds (Seshadri et al, 2002). This observation is in agreement with previously reported values for the sulfonyl group, and is due to the repulsive interaction between the short S O bonds (Seshadri et al, 2002).…”