Abstract
C29H23N7O, triclinic, P1̅ (no. 2), a = 8.2785(12) Å, b = 12.1750(18) Å, c = 13.8122(16) Å, α = 114.401(13)°, β = 103.083(11)°, γ = 93.384(12)°, V = 1216.5(3)Å3, Z = 2, Rgt(F) = 0.0713, wRref(F2) = 0.1880, T = 293(2) K.
Show Summary Details
More options …
More options …
Zeitschrift für Kristallographie - New Crystal Structures
Editor-in-Chief: Huppertz, Hubert
Ed. by Reiß, Guido
6 Issues per year
IMPACT FACTOR 2016: 0.152
Cite Score 2016: 0.15
SCImago Journal Rank (SJR) 2016: 0.123
Source Normalized Impact per Paper (SNIP) 2016: 0.196
Crystal structure of (E)-3-methyl-4-((3-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazol-4-yl)methylene)-1-phenyl-1H-pyrazol-5(4H)-one, C29H23N7O
Gamal A. El-Hiti / Bakr F. Abdel-Wahab / Mohammed B. Alshammari / Amany S. Hegazy / Benson M. Kariuki
Published Online: 2017-01-28 | DOI: https://doi.org/10.1515/ncrs-2016-0243
Open Access
This article offers supplementary material which is provided at the end of the article.
CCDC no.:: 1525575
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 prepared from the reaction of 3-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde with 3-methyl-1-phenyl-1H-pyrazol-5(4H)-one in ethanol in the presence of few drops of piperidine as catalyst under reflux for 1.5 h. The solid obtained on cooling was recrystallized from dimethylformamide to give colorless crystals of the title compound (Mp 267-268 °C) [5].
Experimental details
All hydrogen atoms were placed in calculated positions and refined using a riding model. Methyl C—H bonds were fixed at 0.96 Å, with Uiso = 1.5 Ueq(C), and were allowed to spin about the C—C bond. Aromatic C—H distances were set to 0.93 Å and Uiso of the H atoms set to 1.2 Ueq(C).
Comment
Some triazolylpyrazoles [6, 7] are at the center of attention due to their useful applications as antibacterial, antiviral and antitumor reagents, as well as pesticides and herbicides [8], [9], [10]. The asymmetric unit comprises one molecule of C29H23N7O. The triazole-pyrazole ring system (apart from the methyl protons) is planar with rms deviation of 0.0385 Å. The three phenyl rings are twisted from the triazole-pyrazole system with interplanar angles of 11.08(11)°, 42.42(9)° and 83.62(12)°. In the crystal structure, the planar segments of the molecules form a π-stack along [100].
Acknowledgement
The authors extend their appreciation to the College of Applied Medical Sciences Research Centre and the Deanship of Scientific Research at King Saud University for their funding.
References
- 1
Agilent Technologies: CrysAlisPRO Software system, version 1.171.37.35g, Agilent Technologies UK Ltd, Oxford, UK, (2011). Google Scholar
- 2
Sheldrick, G. M.: A short history of SHELX. Acta Crystallogr. A64 (2008) 112–122. Google Scholar
- 3
Farrugia, L. J.: WinGX and ORTEP for Windows: an update. J. Appl. Crystallogr. 45 (2012) 849–854. Google Scholar
- 4
Cambridge Soft. CHEMDRAW Ultra. Cambridge Soft Corporation, Cambridge, Massachusetts, USA, (2001). Google Scholar
- 5
Abdel-Wahab, B. F.; Mohamed, H. A.; Ali, M. M.: Synthesis and in vitro cytotoxicity of new 3-(5-methyl-1-aryl-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazoles. J. Mod. Med. Chem. 3 (2015) 9–15. Google Scholar
- 6
El Rady, E. A.: An efficient synthesis of some new isolated and fused triazole derivatives. J. Heterocycl. Chem. 50 (2013) E228–E233. CrossrefGoogle Scholar
- 7
Gouda, M. A.: Synthesis and antioxidant evaluation of some novel thiophene, pyrazole, chromene, pyrazolotriazine derivatives bearing sulfonamide moiety. J. Heterocycl. Chem. 53 (2016) doi: . CrossrefGoogle Scholar
- 8
Hutterer, C.; Eickhoff, J.; Milbradt, J.; Korn, K.; Zeitträger, I.; Bahsi, H.; Wagner, S.; Zischinsky, G.; Wolf, A.; Degenhart, C.; Unger, A.; Baumann, M.; Klebl, B.; Marschall, M.: A novel CDK7 inhibitor of the pyrazolotriazine class exerts broad-spectrum antiviral activity at nanomolar concentrations. Antimicrob. Agents Chemother. 59 (2015) 2062–2071. Google Scholar
- 9
Taj, T.; Kamble, R. R.; Kattimani, P. P.; Badami, B. V.: Synthetic utility of sydnones: synthesis of pyrazolines derivatized with 1,2,4-triazoles as anti-hyperglycemic, antioxidant agents and their DNA cleavage study. Med. Chem. Res. 21 (2011) 3709–3719. Google Scholar
- 10
Abdel-Wahab, B. F.; Abdel-Latif, E.; Mohamed, H. A.; Awad, G. E. A.: Design and synthesis of new 4-pyrazolin-3-yl-1,2,3-triazoles and 1,2,3-triazol-4-yl-pyrazolin-1-ylthiazoles as potential antimicrobial agents. Eur. J. Med. Chem. 52 (2012) 263–268. Google Scholar
About the article
Received: 2016-08-08
Accepted: 2017-01-04
Published Online: 2017-01-28
Published in Print: 2017-03-01
Citation Information: Zeitschrift für Kristallographie - New Crystal Structures, Volume 232, Issue 2, Pages 291–293, ISSN (Online) 2197-4578, ISSN (Print) 1433-7266, DOI: https://doi.org/10.1515/ncrs-2016-0243.
©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
Comments (0)