Abstract
C23H17F2N5OS, monoclinic, P21/c (no. 14), a = 5.2272(4) Å, b = 26.7398(15) Å, c = 15.2645(10) Å, β = 97.726(7)°, V = 2114.2(2) Å3, Z = 4, Rgt(F) = 0.0547, wRref(F2) = 0.1371, T = 296(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 (E)-2-(5-(4-fluorophenyl)-3-(furan-2-yl)-4,5-dihydro-1H-pyrazol-1-yl)-5-((4-fluorophenyl)diazenyl)-4-methylthiazole, C23H17F2N5OS
Published Online: 2017-03-18 | DOI: https://doi.org/10.1515/ncrs-2016-0293
Open Access
This article offers supplementary material which is provided at the end of the article.
CCDC no.:: 1533011
The asymmetric unit of the title crystal structure is 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 reaction of a mixture of 1:1 molar ratios of 5-(4-fluorophenyl)-3-(furan-2-yl)-4,5-dihydro-1H-pyrazole-1-carbothioamide and N′-(4-fluorophenyl)-2-oxopropanehydrazonoyl chloride in ethanol under reflux condition for 2 h. The solid obtained on cooling was recrystallized from dimethylformamide to give the title compound as orange crystals in 64% yield, Mp. 225–226 °C [1].
Experimental details
All hydrogen atoms were placed in calculated positions and refined using a riding model. Methyl, methylene and methine C—H bonds were fixed at 0.96 Å, 0.97 Å and 0.98 Å respectively. Displacement parameters were 1.5 times Ueq(C) for methyl groups and 1.2 times Ueq(C) for methylene and methine hydrogens. Methyl groups were allowed to spin about the C—C bond. Aromatic C—H distances were set to 0.93 Å and their Uiso set to 1.2 times Ueq(C).
Discussion
Many pyrazolylthiazoles have been synthesized using different procedures and showed antinociceptive, anti-inflammatory and antimicrobial activities [2], [3], [4], [5], [6], [7], [8], [9], [10]. The X-ray crystal structures for related compounds have been published recently [11, 12].
The asymmetric unit consists of one molecule. In the molecule, the furan(A)-pyrazole(B)-thiazole(C)-fluorophenyl(D) ring system is almost planar. Thus the largest deviation from the least-squares plane through the four rings is 0.22(1) Å (by O1). The greatest difference between the planes through adjacent rings (A and B) is 7.1(2)°. The second fluorophenyl group (E) is almost perpendicular (85.0(5)°) to the A—B—C—D system. In the crystal, pairs of molecules related by an inversion centre interact through two edge-to-face interactions involving rings D and E with centroid-to-centroid distances of 5.3 Å. A short intermolecular O⋯O contact (2.84 Å) occurs between furan moieties of pairs of molecules related by inversion symmetry. Such contact is not unique, as shown by a search of the CSD [13] which gave 78 hits for contacts within the sum of van-der-Waals radii for furan oxygens.
Acknowledgement
The project was supported by King Saud University, Deanship of Scientific Research, Research Chair.
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About the article
Received: 2016-10-03
Accepted: 2017-02-16
Published Online: 2017-03-18
Published in Print: 2017-05-24
Citation Information: Zeitschrift für Kristallographie - New Crystal Structures, Volume 232, Issue 3, Pages 413–415, ISSN (Online) 2197-4578, ISSN (Print) 1433-7266, DOI: https://doi.org/10.1515/ncrs-2016-0293.
©2017 Gamal A. El-Hiti et al., published by De Gruyter, Berlin/Boston. This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License. BY-NC-ND 3.0
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