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The Crystal Structure of N-[(2E)-3-(4-Chlorophenyl)prop-2-en-1-yl]-4-methoxy-N-methylbenzenesulfonamide

  • Benedetta Carrozzini
  • Benny Danilo Belviso
  • Claudio Bruno
  • Maria Maddalena Cavalluzzi
  • Angelo Lovece
  • Giovanni Lentini
  • Rocco Caliandro
Original Paper

Abstract

The title compound C17H18ClNO3S crystallizes in the monoclinic P21/c space group with unit cell parameters a = 15.040 (3) Å, b = 9.151 (6) Å, c = 13.868 (7) Å, β = 116.38 (5)°. Chlorophenyl and methoxyphenyl ring planes are approximately perpendicular and the two moieties form an angle of 82.2°. The crystal packing is stabilized by π–π and Cl–π interactions, which occur between parallel methoxyphenyl and chlorophenyl moieties. Dipolar intermolecular contacts, mainly involving the oxygen atoms and C–H, also contribute to the crystal network.

Graphical Abstract

The title compound is formed in the synthetic route for the production of potent inhibitors of calmodulin. Its crystal structure shows the chlorophenyl and methoxyphenyl moieties forming an angle of 82.2°. The crystal packing is stabilized by π–π, Cl–π and dipolar intermolecular contacts.

Keywords

Ca2+/calmodulin-dependent protein kinase II Tertiary sulfonamide KN-92 KN-93 π–π interactions Cl–π interactions 

Notes

Acknowledgements

We thank Giuseppe Chita for assistance in X-ray diffraction measurements.

Supplementary material

10870_2018_739_MOESM1_ESM.pdf (101 kb)
Supplementary material 1 (PDF 101 KB)

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Istituto di Cristallografia – CNRBariItaly
  2. 2.Dipartimento di Farmacia – Scienze del FarmacoUniversità degli Studi di Bari Aldo MoroBariItaly

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