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Synthesis, molecular and crystal structure analysis of 1-(4-Methylbenzenesulfonyl)indole-3-carbaldehyde and DFT investigation of its rotational conformers

Zukerman-Schpector J 1 , Madureira LS 2 , Wulf GD 3 , Stefani HA 4 , Vasconcelos SN 5 , Ng SW 6 Show all authors , Tiekink ER 7

Affiliations 

  • 1 Laboratório de Cristalografia, Estereodinâmica e Modelagem Molecular, Departamento de Química, Universidade Federal de São Carlos, C.P.676, São Carlos, SP, 13565-905, Brazil. julio@power.ufscar.br
  • 2 Laboratório de Cristalografia, Estereodinâmica e Modelagem Molecular, Departamento de Química, Universidade Federal de São Carlos, C.P.676, São Carlos, SP, 13565-905, Brazil. lucassousamadureira@gmail.com
  • 3 Laboratório de Cristalografia, Estereodinâmica e Modelagem Molecular, Departamento de Química, Universidade Federal de São Carlos, C.P.676, São Carlos, SP, 13565-905, Brazil. glaudeston_@hotmail.com
  • 4 Departamento de Farmácia, Faculdade de Ciências Farmacêuticas, Universidade de São Paulo, 05508-900, SP, Brazil. hstefani@usp.br
  • 5 Departamento de Farmácia, Faculdade de Ciências Farmacêuticas, Universidade de São Paulo, 05508-900, SP, Brazil. stanleynsv@gmail.com
  • 6 Department of Chemistry, The University of Malaya, Kuala Lumpur 50603, Malaysia. mseikweng@um.edu.my
  • 7 Department of Chemistry, The University of Malaya, Kuala Lumpur 50603, Malaysia. edward.tiekink@gmail.com
Molecules, 2014;19(2):1990-2003.
PMID: 24531216 DOI: 10.3390/molecules19021990

Abstract

Two independent molecules that differ in terms of rotation about the central S-N bond comprise the asymmetric unit of the title compound 1. The molecules have a V-shape with the dihedral angles between the fused ring system and benzene ring being 79.08(6)° and 72.83(5)°, respectively. The packing is mostly driven by p···p interactions occurring between the tolyl ring of one molecule and the C6 ring of the indole fused ring system of the other. DFT and IRC calculations for these and related 1-(arylsulfonyl)indole molecules showed that the rotational barrier about the S-N bond between conformers is within the 2.5-5.5 kcal/mol range. Crystal data for C16H13NO3S (1): Mr = 299.33, space group Pna21, a = 19.6152(4) Å, b = 11.2736(4) Å, c = 12.6334(3) Å, V = 2793.67(13) Å3, Z = 8, Z' = 2, R = 0.034.

* Title and MeSH Headings from MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine.

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