title: Synthesis, molecular and crystal structure analysis of 1-(4-Methylbenzenesulfonyl)indole-3-carbaldehyde and DFT investigation of its rotational conformers.
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.
authors: 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.
authors: Julio
authors: J
authors: Zukerman-Schpector
authors: 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.
authors: Lucas Sousa
authors: LS
authors: Madureira
authors: 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.
authors: Glaudeston Dutra
authors: GD
authors: Wulf
authors: Departamento de Farmácia, Faculdade de Ciências Farmacêuticas, Universidade de São Paulo, 05508-900, SP, Brazil. hstefani@usp.br.
authors: Hélio A
authors: HA
authors: Stefani
authors: Departamento de Farmácia, Faculdade de Ciências Farmacêuticas, Universidade de São Paulo, 05508-900, SP, Brazil. stanleynsv@gmail.com.
authors: Stanley N S
authors: SN
authors: Vasconcelos
authors: Department of Chemistry, The University of Malaya, Kuala Lumpur 50603, Malaysia. mseikweng@um.edu.my.
authors: Seik Weng
authors: SW
authors: Ng
authors: Department of Chemistry, The University of Malaya, Kuala Lumpur 50603, Malaysia. edward.tiekink@gmail.com.
authors: Edward R T
authors: ER
authors: Tiekink
mesh_terms: D001555:Benzene Derivatives / Q000138:chemical synthesis / Q000737:chemistry*; D018360:Crystallography, X-Ray; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: D001555:Benzene Derivatives; D007211:Indoles; C012381:indole-3-carbaldehyde; C030374:indole