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Crystal structure, Hirshfeld surfaces, topology, energy frameworks and dielectric studies of 1-(2-chlorophenyl)- 3,3-bis(methylthio)prop-2-en-1-one

  • Shankar Madan Kumar EMAIL logo , Byrapura Chandregowda Hemraju , Seegehalli Manjegowda Anil , Neralekere Kenchegowda Manjunatha , Menasagere Thammannagowda Swamy , Neratur Krishnappagowda Lokanath , Mohammed Al-Ghorbani , Nabil Al-Zaqri and Ali Alsalme


The title compound 1-(2-chlorophenyl)-3,3-bis(methylthio)prop-2-en-1-one (1) have been synthesized, crystallized and characterized using FT-IR, 1H NMR, 13C NMR, LCMS and confirmed by single crystal X-ray diffraction method. In addition, the intermolecular interactions in the crystal structure are analyzed using Hirshfeld surfaces computational method. The (1) crystallizes in a monoclinic crystal system (space group P 21/c) with cell parameters a = 17.0132(9) Å, b = 8.6521(4) Å, c = 8.2815(7) Å, β = 95.512(6) ° and Z = 4. Intermolecular hydrogen bonds/interactions of the type C · · · H · · · O, C–H · · · S, C–H · · · Cg and C–Cl · · · Cg stabilize the crystal structure. The intermolecular interactions responsible for crystal packing are analyzed using Hirshfeld surfaces computational method, 2D finger print plots, electrostatic potential surfaces, toplogy surfaces [curvedness (C) and shape index (S), enrichment ratio (E) and 3D energy frameworks]. In addition the dielectric studies were performed for the title molecule. The crystal structure database (CSD) analysis was carried out for structural conformation and crystal packing confirmation. Overall structural studies confirmed that the intermolecular interactions of the type S · · · S chalocogen bonds are involved in crystal packing in addition to the C11–H11 · · · O1, C10–H10B · · · O1, two C10–H10 · · · S1, C4–H11 · · · Cg1 and C1–Cl1 · · · Cg1 interactions.

Corresponding author: Dr. Shankar Madan Kumar, IOE, Vijnana Bhavana, University of Mysore, Mysore 570006, India, E-mail:


Authors thanks IOE and DST-PURSE, Vijnana Bhavana, University of Mysore, Mysuru for X-ray crystallographic facility. Researchers Supporting Project number (RSP-2019/78), King Saud University, Riyadh, Saudi Arabia.


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Supplementary Material

The online version of this article offers supplementary material (

Received: 2019-11-21
Accepted: 2020-01-17
Published Online: 2020-02-04
Published in Print: 2020-03-26

©2020 Walter de Gruyter GmbH, Berlin/Boston

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