Abstract
C20H17N5O, triclinic, P1̅ (no. 2), a = 11.5358(7) Å, b = 13.8746(9) Å, c = 16.3942(10) Å, α = 85.958(5)°, β = 87.407(5)°, γ = 87.619(5)°, V = 2612.8(3)Å3, Z = 6, Rgt(F) = 0.0607, wRref(F2) = 0.1510, T = 293(2) K.
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Zeitschrift für Kristallographie - New Crystal Structures
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Crystal structure of 3-(5-methyl-1-p-tolyl-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde, a rare Z′ = 3 structure, C20H17N5O
Published Online: 2017-01-24 | DOI: https://doi.org/10.1515/ncrs-2016-0258
Open Access
This article offers supplementary material which is provided at the end of the article.
CCDC no.:: 1525576
The asymmetric unit of the title crystal structure, with three crystallographically independent molecules, is shown in the figure. Tables 1 and 2 contain details of the measurement method 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
3-(5-Methyl-1-p-tolyl-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde was synthesized from treatment of 5-methyl-4-((2-phenylhydrazono)methyl)-1-p-tolyl-1H-1,2,3-triazole with phosphorus oxychloride and dimethylformamide (Vilsmeier-Haack reaction) at 0–5 °C. The reaction was left overnight at room temperature, poured onto ice-cold water and neutralized with ammonium hydroxide solution (5%). The solid obtained was filtered, dried and recrystallized from dimethylformamide to give colorless crystals of the title compound (Mp 229–230 °C) [5].
Experimental details
Non-hydrogen atoms were refined with anisotropic diaplacement parameters. 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 isotropic displacement parameters of the corresponding hydrogen atoms set to 1.5 times Ueq(C), and were allowed to spin about the C—C bond. Aromatic C—H distances were set to 0.93 Å and Uiso parameters of aromatic hydrogen atoms were set to 1.2 times the Ueq of the atoms to which they are bonded. The methyl group C41 shows a disorder of its hydrogen atoms (cf. the figure).
Comment
Compounds containing a pyrazole ring system [6], [7], [8], [9], [10] exhibit a wide range of biological applications. Hence, it has been shown that many derivatives show antimicrobial, fungicidal, anticancer and antioxidant activities [11], [12], [13], [14].
The asymmetric unit comprises three crystallographically independent molecules of C20H17N5O. Molecular conformation in the three molecules is very similar with twist angles between the triazole, pyrazole and phenyl rings ranging from 2.40(14) to 18.71(11)° (cf. the figure). The twist between the triazole and methylbenzene groups is greater in all three molecules, being in the range 47.53(8)–58.30(8)°. In the crystal structure, the molecules stack with planes roughly parallel to (011). All bond lengths and angles are in the expected ranges.
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: 2017-01-04
Published Online: 2017-01-24
Published in Print: 2017-03-01
Citation Information: Zeitschrift für Kristallographie - New Crystal Structures, Volume 232, Issue 2, Pages 313–315, ISSN (Online) 2197-4578, ISSN (Print) 1433-7266, DOI: https://doi.org/10.1515/ncrs-2016-0258.
©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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