Synthesis, Molecular and Crystal Structure Analysis of 1-(4-Methylbenzenesulfonyl)indole-3-carbaldehyde and DFT Investigation of Its Rotational Conformers
Julio Zukerman-Schpector,
Lucas Sousa Madureira,
Glaudeston Dutra Wulf,
Hélio A. Stefani,
Stanley N. S. Vasconcelos,
Seik Weng Ng,
Edward R. T. Tiekink
Affiliations
Julio Zukerman-Schpector
Laboratório de Cristalografia, Estereodinâmica e Modelagem Molecular, Departamento de Química, Universidade Federal de São Carlos, C.P.676, São Carlos, SP, 13565-905, Brazil
Lucas Sousa Madureira
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 Dutra Wulf
Laboratório de Cristalografia, Estereodinâmica e Modelagem Molecular, Departamento de Química, Universidade Federal de São Carlos, C.P.676, São Carlos, SP, 13565-905, Brazil
Hélio A. Stefani
Departamento de Farmácia, Faculdade de Ciências Farmacêuticas, Universidade de São Paulo, 05508-900, SP, Brazil
Stanley N. S. Vasconcelos
Departamento de Farmácia, Faculdade de Ciências Farmacêuticas, Universidade de São Paulo, 05508-900, SP, Brazil
Seik Weng Ng
Department of Chemistry, The University of Malaya, Kuala Lumpur 50603, Malaysia
Edward R. T. Tiekink
Department of Chemistry, The University of Malaya, Kuala Lumpur 50603, Malaysia
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.
