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Investigation of the crystal structures and Hirshfeld surfaces of three closely related N-(2-fluorobenzoyl)-arylsulfonamides

  • Parameshwar Adimule Suchetan EMAIL logo , Gundagallu Madanagopala Reddy Supriya , Kalavala Shivaprakash Srivishnu , Hanumanahalli Nagaraju Lakshmikantha , Shivalingegowda Naveen and Neratur Krishnappagowda Lokanath
Published/Copyright: May 24, 2016
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Zeitschrift für Kristallographie - Crystalline Materials
From the journal Zeitschrift für Kristallographie - Crystalline Materials Volume 231 Issue 6

Abstract

The investigation of the crystal structures of three closely related sulfonamides, namely N-(2-fluorobenzoyl)-2-methylbenzenesulfonamide (I), N-(2-fluorobenzoyl)-4-methylbenzenesulfonamide (II) and N-(2-fluorobenzoyl)-2-chlorobenzenesulfonamide (III) by analysing intermolecular interactions and the packing patterns, and also by Hirshfeld surface analyses is presented. Compound (I) has a three-dimensional (3D) network, in which N–H···O and C–H···F chains build up two-dimensional (2D) arrays, which are extended into a 3D network through C–H···π interactions. In (II), alternating N–H···O and C–H···O rings form one-dimensional (1D) ribbons, which are interconnected by C–H···π interactions to build a 2D network. In (III), 2D sheets comprising N–H···O rings, C–H···π chains, Cl···F and F···F contacts are stacked by π···π interactions to form a 3D network. Hirshfeld surface analyses, comprising dnorm surfaces, curvedness and 2D fingerprint (FP) plots, for all three molecules were also conducted to verify the importance of the different intermolecular interactions.

Keywords: crystal structure analysis; Hirshfeld surface; hydrogen bonding; sulfonamides; X-ray diffraction

Acknowledgments:

The authors are thankful to the Institution of Excellence, VijnanaBhavana, University of Mysore, Manasagangotri, Mysore, for providing the single-crystal X-ray diffraction data. GMS thanks the Vision Group of Science and Technology (VGST), Karnataka, India, for financial support under its SPiCE project scheme.

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Supplemental Material:

The online version of this article (DOI: 10.1515/zkri-2016-0001) offers supplementary material, available to authorized users.

Received: 2016-1-3
Accepted: 2016-4-13
Published Online: 2016-5-24
Published in Print: 2016-6-1

©2016 by De Gruyter

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https://doi.org/10.1515/zkri-2016-0001
Keywords for this article
crystal structure analysis; Hirshfeld surface; hydrogen bonding; sulfonamides; X-ray diffraction

Articles in the same Issue

  1. Frontmatter
  2. Graphical Synopsis
  3. Inorganic Crystal Structures
  4. Ni4 and Ni3Ga clusters as building units in Ca3Ni4Ga4 and Sr3Ni3□Ga4
  5. Crystallographic, DFT and docking (cathepsin B) studies on an organotellurium(IV) compound
  6. Organic and Metalorganic Crystal Structures
  7. Structural systematics of aryl-1,3-dithiane derivatives: crystal and energy-minimised structures, and Hirshfeld surface analysis
  8. Bis(phosphane)copper(I) and silver(I) dithiocarbamates: crystallography and anti-microbial assay
  9. Nanoscratching meets nanoindentation
  10. Hydrogen bonding in 2,6-bis(4-fluorophenyl)-3,5-dimethylpiperidin-4-one methanol solvate
  11. Investigation of the crystal structures and Hirshfeld surfaces of three closely related N-(2-fluorobenzoyl)-arylsulfonamides
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