Two isomorphous series of 2′-(2,5-dichlorothiophene-3-carbonyl)-1′-(aryl)-1′,2′,5′,6′,7′,7a'-hexahydrospiro[indoline-3,3′-pyrrolizin]-2-one derivatives: X-ray structures, intermolecular interactions, Hirshfeld analysis and molecular docking

• Published in: Journal of molecular structure 2024-04, Vol.1302, p.137395, Article 137395
• Main Authors: Ali, Basem F., Al-Refai, Mahmoud, Al-Masri, Eman, Shtaiwi, Amneh, Aljaar, Nayyef, Geyer, Armin, Ivlev, Sergei I.
• Format: Article
• Language: English
• Subjects: 2,5-dichlorothiophene; Crystal structure; Crystal supramolecularity; Intermolecular interactions; Molecular docking; Spiro[indoline-pyrrolizin]-2-one
• ISSN: 0022-2860
• DOI: 10.1016/j.molstruc.2023.137395

•Isomorphous spiro[indoline-3,3′-pyrrolizin]-2-ones contains 2,5-dichlorothiophene-3-carbonyl) and aryl substituents.•X-ray structural analysis and crystal supramolecularity are studied.•Hirshfeld analysis of intermolecular interactions.•Molecular docking suggests the potential for further evaluated in vitro and in vivo for cancer drug discovery. Two isomorphous series of 2′-(2,5-dichlorothiophene-3-carbonyl)-1′-(aryl)-1′,2′,5′,6′,7′,7a'-hexahydrospiro[indoline-3,3′-pyrrolizin]-2-one derivatives are reported. The first series contains namely, 1′-(2-bromophenyl)-2′-(2,5-dichlorothiophene-3-carbonyl)-1′,2′,5′,6′,7′,7a'-hexahydrospiro[indoline-3,3′-pyrrolizin]-2-one, C25H19BrCl2N2O2S, (I), 2′-(2,5-dichlorothiophene-3-carbonyl)-1′-(o-tolyl)-1′,2′,5′,6′,7′,7a'-hexahydrospiro[indoline- 3,3′-pyrrolizin]-2-one, C26H22Cl2N2O2S, (II), and (1′R,2′S,7a'S)-2′-(2,5-dichlorothiophene-3-carbonyl)-1′-(m-tolyl)-1′,2′,5′,6′,7′,7a'-hexahydrospiro[indoline-3,3′-pyrrolizin]-2-one, C26H22Cl2N2O2S, (III), are isomorphous in space group P1¯. The second series of 2′-(2,5-dichlorothiophene-3-carbonyl)-1′-(4-methoxyphenyl)-1′,2′,5′,6′,7′,7a'-hexahydrospiro[indoline-3,3′-pyrrolizin]-2-one, C27H26Cl2N2O4S, (IV), 2′-(2,5-dichlorothiophene-3-carbonyl)-1′-(p-tolyl)-1′,2′,5′,6′,7′,7a'-hexahydrospiro[indoline-3,3′-pyrrolizin]-2-one, C27H26Cl2N2O3S, (V) and 1′-(3-bromophenyl)-2′-(2,5-dichlorothiophene-3-carbonyl)-1′,2′,5′,6′,7′,7a'-hexahydrospiro[indoline-3,3′-pyrrolizin]-2-one, C26H23BrCl2N2O3S, (VI) are isomorphous in space group P21/c. In each of compounds (I–III), a combination of N—H∙∙∙O and C—H∙∙∙O hydrogen bonds generates a chain of an alternating centrosymmetric edge-fused rings of R22(8) [(π)N—H∙∙∙O—C(π)] and R42(14) [(π)C/N—H∙∙∙O—C(π)]. These chains are further linked along the b-axis by π∙∙∙π stacks of the thiophene rings. Inter-sheets C—H∙∙∙π contacts propagate along [100] contributing to the supramolecular assembly. In the series (IV–VI), both N—H∙∙∙O and C—H∙∙∙O hydrogen bonds generate sheets in cb plane, composed of centrosymmetric dimers of molecules linked through (π)C—H∙∙∙O—C(π) hydrogen bonding into R22(24) [in (IV)] or R22(14) [in (V and VI)] ring motifs. The dimers are further connected by the solvent MeOH molecules by another ring motif R32 (8) rings through (π)C—H∙∙∙O—C(π), (π)N—H∙∙∙O—(MeOH) and CH3OH∙∙∙O—C(π) hydrogen bonding. Intermolecular interactions were visualized using Hirshfeld surface analysis and the major contacts found to be delineated into H∙∙∙H, H∙∙∙Cl/C