Abstract
C23H16ClN5S, monoclinic, P21/n (no. 14), a = 19.8348(9) Å, b = 8.8376(3) Å, c = 23.8486(10) Å, β = 97.646(4)°, V = 4143.3(3) Å3, Z = 8, Rgt(F) = 0.0492, wRref(F2) = 0.1276, T = 293(2) K.
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Zeitschrift für Kristallographie - New Crystal Structures
Editor-in-Chief: Huppertz, Hubert
Ed. by Reiß, Guido
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Crystal structure of 5-(5-(4-chlorophenyl)-1-phenyl-1H-pyrazol-3-yl)-N-phenyl-1,3,4-thiadiazol-2-amine, C23H16ClN5S
Published Online: 2017-02-07 | DOI: https://doi.org/10.1515/ncrs-2016-0259
Open Access
This article offers supplementary material which is provided at the end of the article.
CCDC no.:: 1526218
The two crystallographically independent molecules of the title crystal structure are shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters.
Table 1
Data collection and handling.
Table 2
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).
Source of material
The title compound was synthesized from treatment of 2-(5-(4-chlorophenyl)-1-phenyl-1H-pyrazole-3-carbonyl)-N-phenylhydrazinecarbothioamide with concentrated sulfuric acid in an ice bath for 1 h. This reaction mixture was left to stir at room temperature overnight, poured into cooled water and then neutralized with an aqueous sodium hydroxide solution. The solid formed was filtered, dried and recrystallized from dimethylformamide to give needle-shaped colourless crystals of the title compound (Mp. 212–213 °C) [1].
Experimental details
All hydrogen atoms were placed in calculated positions and refined using a riding model. N—H bonds were fixed at 0.86 Å, with displacement parameters 1.2Ueq(N). Aromatic C—H distances were set to 0.93 Å and their U(iso) set to 1.2Ueq for the atoms to which they are bonded.
Discussion
1,3,4-Thiadiazole ring systems [2, 3] are present in a number of natural products and have a wide range of pharmacological activities such as antibacterial, antifungal, anticancer, antioxidant and anticonvulsant [4], [5], [6], [7], [8].
The asymmetric unit comprises two molecules (I and II) of C23H16ClN5S with slightly different conformations. The twist angles about the bonds between the (phenylamino)-(thiadiazole)-(pyrazole)-(chlorophenyl) groups are 15.13(10)°, 10.49(13)° and 39.56(10)° respectively for one molecule and 22.11(7)°, 8.06(12)° and 30.04(8)° for the other molecule. The angle between the (pyrazole)-(phenyl) groups are 49.07(10)° for I and 52.32(9)° for II. Bond lengths and angles are all in the expected ranges. The two crystallographically independent molecules of the title crystal structure are pairwise connected by two N—H⋯N hydrogen bonds.
Acknowledgement
The project was supported by King Saud University, Deanship of Scientific Research, Research Chair.
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About the article
Received: 2016-08-26
Accepted: 2017-01-10
Published Online: 2017-02-07
Published in Print: 2017-03-01
Citation Information: Zeitschrift für Kristallographie - New Crystal Structures, Volume 232, Issue 2, Pages 317–319, ISSN (Online) 2197-4578, ISSN (Print) 1433-7266, DOI: https://doi.org/10.1515/ncrs-2016-0259.
©2017 Gamal A. El-Hiti et al., published by De Gruyter.. This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License. BY-NC-ND 3.0
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