Skip to content
Licensed Unlicensed Requires Authentication Published by De Gruyter (O) July 3, 2015

Investigation of the crystal structures of N-(4-fluorobenzoyl)benzenesulfonamide and N-(4-fluoro-benzoyl)-4-methylbenzenesulfonamide

  • Parameshwar Adimule Suchetan EMAIL logo , Swamy Sreenivasa , Kalavala Shivaprakash Srivishnu , Hanumanahalli Nagaraju Lakshmikantha , Gundagallu Madanagopalareddy Supriya , Shivalingegowda Naveen and Neratur Krishnappagowda Lokanath

Abstract

The crystal structures of two closely related compounds, namely, N-(4-fluorobenzoyl)-benzenesulfonamide (I) and N-(4-fluorobenzoyl)-4-methylbenzenesulfonamide (II) are investigated by analysing the packing patterns and intermolecular interactions, and also by Hirshfeld surface analysis. The crystal structure of each of (I) and (II) displays a two-dimensional architecture. Hirshfeld surfaces comprising dnorm surface and 2D fingerprint plots were analysed for both molecules in order to understand the relationship between the crystal structures. The analysis shows that the lengths of the observed hydrogen bonds and other intermolecular interactions in (II) are relatively shorter than those observed in (I). Further, the analysis demonstrates the predominant participation of the sulfonyl-O atom and the carbonyl-O atom as the hydrogen bond acceptors in (I) and (II), respectively.


Corresponding author: Parameshwar Adimule Suchetan, Department of Chemistry, University College of Science, Tumkur University, Tumkur-3, India, E-mail:

Acknowledgements

The authors are thankful to the Institution of Excellence, Vijnana Bhavana, University of Mysore, Mysore, for providing the single-crystal X-ray diffraction data. PAS thanks the University Grants Commission (UGC), India, for financial support under its Minor Research Project Scheme.

References

[1] N. R. Mohan, S. Sreenivasa, K. E. Manojkumar, T. Madhu Chakrapani Rao, J. Appl. Chem. 2013, 2, 722.Search in Google Scholar

[2] K. E. Manojkumar, S. Sreenivasa, N. R. Mohan, T. Madhu Chakrapani Rao, T. Harikrishna, J. Appl. Chem. 2013, 2, 730.Search in Google Scholar

[3] A. S. Hamad, F. S. Abed, J. Appl. Chem. 2014, 3, 56.Search in Google Scholar

[4] T. Hasegawa, H. Yamamoto, Bull. Chem. Soc. Jpn. 2000, 73, 423.Search in Google Scholar

[5] M. G. Banwell, C. F. Crasto, C. J. Easton, A. K. Forrest, T. Karoli, D. R. March, L. Mensah, M. R. Nairn, P. J. O’Hanlon, M. D. Oldham, W. Yue, Bioorg. Med. Chem. Lett. 2000, 10, 2263.Search in Google Scholar

[6] L. L. Chang, W. T. Ashton, K. L. Flanagan, T. B. Chen, S. S. O’Malley, G. J. Zingaro, P. K. S. Siegl, S. D. Kivlighn, V. J. Lotti, R. S. L. Chang, W. J. Greenlee, J. Med. Chem. 1994, 37, 4464.Search in Google Scholar

[7] J. H. Musser, A. F. Kreft, R. H. W. Bender, D. M. Kubrak, D. Grimes, R. P. Carlson, J. M. Hand, J. Chang, J. Med. Chem. 1990, 3, 240.Search in Google Scholar

[8] K. L. Lobb, P. A. Hipskind, J. A. Aikins, E. Alvarez, Y. Cheung, E. L. Considine, A. De Dios, G. L. Durst, R. Ferritto, C. S. Grossman, D. D. Giera, B. A. Hollister, Z. Huang, P. W. Iversen, K. L. Law, T. Li, H.–S. Lin, B. Lopez, J. E. Lopez, L. M. Martin Cabrejas, D. J. McCann, V. Molero, J. E. Reilly, M. E. Richett, C. Shih, B. Teicher, J. H. Wikel, W. T. White, M. Mader, J. Med. Chem. 2004, 47, 5367.Search in Google Scholar

[9] M. Mader, C. Shih, E. Considine, A. De Dios, C. Grossman, P. Hipskind, H. Lin, K. Lobb, B. Lopez, J. Lopez, L. Cabrejas, M. Richett, W. White, Y. Cheung, Z. Huang, J. Reilly, S. Dinn, Bioorg. Med. Chem. Lett. 2005, 15, 617.Search in Google Scholar

[10] B. T. Gowda, S. Foro, P. A. Suchetan, H. Fuess, Acta Crystallogr. Sect. E, Struct Rep. 2009, 65, 2516.Search in Google Scholar

[11] P. A. Suchetan, B. T. Gowda, S. Foro, H. Fuess, Acta Crystallogr. Sect. E, Struct Rep. 2010, 66, 1039.Search in Google Scholar

[12] P. A. Suchetan, B. T. Gowda, S. Foro, H. Fuess, Acta Crystallogr. Sect. E, Struct Rep. 2009, 65, 3156.Search in Google Scholar

[13] P. A. Suchetan, B. T. Gowda, S. Foro, H. Fuess, Acta Crystallogr. Sect. E, Struct Rep. 2010, 66, 327.Search in Google Scholar

[14] P. A. Suchetan, B. T. Gowda, S. Foro, H. Fuess, Acta Crystallogr. Sect. E, Struct Rep. 2010, 66, 1772.Search in Google Scholar

[15] P. A. Suchetan, B. T. Gowda, S. Foro, H. Fuess, Acta Crystallogr. Sect. E, Struct Rep. 2010, 66, 1510.Search in Google Scholar

[16] S. Sreenivasa, M. S. Nanjundaswamy, S. Madankumar, N. K. Lokanath, E. Suresha, P. A. Suchetan, Acta Crystallogr. Sect. E, Struct Rep. 2014, 70, 192.Search in Google Scholar

[17] S. Sreenivasa, B. S. Palakshamurthy, J. Tonannavar, Y. Jayashree, A. G. Sudha, P. A. Suchetan, Acta Crystallogr. Sect. E, Struct Rep. 2013, 69, 1664.Search in Google Scholar

[18] K. S. Saikat, CrystEngComm. 2013, 9, 1772.Search in Google Scholar

[19] K. S. Saikat, J. Mol. Structure. 2014, 1064, 70.Search in Google Scholar

[20] M. A. Spackman, J. J. McKinnon, CrystEngComm. 2002, 4, 378.Search in Google Scholar

[21] M. A. Spackman, J. J. McKinnon, D. Jayatilaka, CrystEngComm. 2008, 10, 377.Search in Google Scholar

[22] Bruker. APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA, 2004.Search in Google Scholar

[23] G. M. Sheldrick, Acta Crystallogr. Sect. A. 2015, 71, 3.Search in Google Scholar

[24] L. J. Farrugia, J. Appl. Cryst. 2012, 45, 849.Search in Google Scholar

[25] C. F. Macrae, I. J. Bruno, J. A. Chisholm, P. R. Edgington, P. McCabe, E. Pidcock, L. Rodriguez-Monge, R. Taylor, J. van de Streek, P. A. Wood, J. Appl. Cryst. 2008, 41, 466.Search in Google Scholar

[26] S. K. Wolff, D. J. Grimwood, J. J. McKinnon, D. Jayatilaka, M. A. Spackman, Crystal Explorer 3.0, University of Western Australia, Perth, Australia, 2001.Search in Google Scholar

[27] D. Jayatilaka, D. J. Grimwood, A. Lee, A. Lemay, A. J. Russel, C. Taylo, S. K. Wolff, C. Chenai, A. Whitton, TONTO – A System for Computational Chemistry, 2005. Available at: http://hirshfeldsurface.net/Search in Google Scholar


Supplemental Material:

The online version of this article (DOI: 10.1515/zkri-2014-1832) offers supplementary material, available to authorized users.


Received: 2014-12-22
Accepted: 2015-5-6
Published Online: 2015-7-3
Published in Print: 2015-8-1

©2015 by De Gruyter

Downloaded on 27.4.2024 from https://www.degruyter.com/document/doi/10.1515/zkri-2014-1832/html
Scroll to top button