Crystal structures of ethyl (2S*,2′R*)-1′-methyl-2′′,3-dioxo-2,3-dihydrodispiro[1-benzothiophene-2,3′-pyrrolidine-2′,3′′-indoline]-4′-carboxylate and ethyl (2S*,2′R*)-5′′-chloro-1′-methyl-2′′,3-dioxo-2,3-dihydrodispiro[1-benzothiophene-2,3′-pyrrolidine-2′,3′′-indoline]-4′-carboxylate

Abstract

In the title compounds, C22H20N2O4S, (I), and C22H19ClN2O4S, (II), the pyrrolidine rings have twist conformations on the spiro–spiro C—C bonds. In (I), the five-membered ring of the oxindole moiety has an envelope conformation with the spiro C atom as the flap, while in (II) this ring is flat (r.m.s. deviation = 0.042 Å). The mean planes of the pyrrolidine rings are inclined to the mean planes of the indole units [r.m.s deviations = 0.073 and 0.069 Å for (I) and (II), respectively] and the benzothiophene ring systems (r.m.s. deviations = 0.019 and 0.034 Å for (I) and (II), respectively) by 79.57 (8) and 88.61 (7)° for (I), and by 81.99 (10) and 88.79 (10)° for (II). In both compounds, the ethoxycarbonyl group occupies an equatorial position with an extended conformation. The overall conformation of the two molecules differs in the angle of inclination of the indole unit with respect to the benzothiophene ring system, with a dihedral angle between the planes of 71.59 (5) in (I) and 82.27 (7)° in (II). In the crystal of (I), molecules are linkedviapairs of N—H...O hydrogen bonds, forming inversion dimers enclosingR22(14) loops. The dimers are linkedviaC—H...O and bifurcated C—H...O(O) hydrogen bonds, forming sheets lying parallel to (100). In the crystal of (II), molecules are again linkedviapairs of N—H...O hydrogen bonds, forming inversion dimers but enclosing smallerR22(8) loops. Here, the dimers are linked by C—H...O hydrogen bonds, forming ribbons propagating along [010].

Crystal structure of ethyl 1′,1′′-dimethyl-2′′,3-dioxo-3H-dispiro[benzo[b]thiophene-2,3′-pyrrolidine-2′,3′′-indoline]-4′-carboxylate

“…1. The geometric parameters of the title molecule agrees well with those reported for similar structures (Savithri et al, 2014).…”

“…For various biological activities of indole derivatives, see: Harris & Uhle (1960); Ho et al (1986); Stevenson et al (2000). For the crystal structures of two very similar compounds, see: Savithri et al (2014 Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008(Sheldrick, , 2015; molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).…”

Crystal structure of methyl 1-(4-fluorobenzyl)-4-methoxy-5-oxopyrrolidine-3-carboxylate, C14H16FNO4

“…The puckering parameters [8] for the pyrrolidine ring, which makes an angle of 76.85(6)°with the phenyl ring, are Q = 0.3026 Å and ϕ = 282.5416°. The N-C and C-C bonds lengths, and the C-C-N and C-N-C angles in the pyrrolidine ring are comparable with those in other pyrrolidines [5,9,10]. The phenyl ring is planar and stacked over one another with a centroid-centroid distance of 4.432(2) Å.…”

“…Optically active pyrrolidines have been used as intermediates, chiral ligands or auxiliaries in controlled asymmetric synthesis [5]. Pyrrolidine compounds are reported to exhibit antifungal [6] and anti-influenza virus [7].…”

15-(4-Chlorophenyl)-6b-hydroxy-17-methyl-6b,7,16,17-tetrahydro-7,14a-methanonaphtho[1′,8′:1,2,3]pyrrolo[3′,2′:8,8a]azuleno[5,6-b]quinolin-14(15H)-one methanol hemisolvate

“…Optically active pyrrolidines have been used as intermediates, chiral ligands or auxiliaries in controlled asymmetric synthesis (Savithri et al, 2014). Pyrrolidine compounds are reported to exhibit antimicrobial, antifungal (Govind et al,2003), anti-influenza virus A (Stylianakis et al, 2003), anti-inflammatory and antitumor (Li & Xu, 2004) activities.…”