Abstract
C18H20FN3S, triclinic, P1̅, a = 7.3884(4) Å, b = 10.0741(6) Å, c = 12.6533(8) Å, α = 69.209(2)°, β = 73.778(2)°, γ = 72.638(2)°, V = 824.33(8) Å3, Z = 2, Rgt(F) = 0.0480, wRref(F2) = 0.1351, T = 296(2) K.
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Zeitschrift für Kristallographie - New Crystal Structures
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Crystal structure of 3-(adamantan-1-yl)-4-(4-fluorophenyl)-1H-1,2,4-triazole-5(4H)-thione, C18H20FN3S
Published Online: 2017-04-01 | DOI: https://doi.org/10.1515/ncrs-2016-0309
Open Access
This article offers supplementary material which is provided at the end of the article.
CCDC no.:: 1507728
The 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
4-Fluorophenyl isothiocyanate (1.53 g, 0.01 mol) was added to a solution of adamantane-1-carbohydrazide (1.94 g, 0.01 mol), in ethanol (10 mL), and the mixture was heated under reflux with stirring for one hour. The solvent was then distilled off in vacuo; an aqueous sodium hydroxide solution (10%, 15 mL) was added to the residue and the mixture was heated under reflux for two hours then filtered hot. On cooling, the mixture was acidified with hydrochloric acid (pH 1–2) and the precipitated crude product was filtered, washed with water, dried and crystallized from aqueous ethanol to yield 3.03 g (92%) of the title compound (C18H20FN3S) as fine transparent block crystals. M.P.: > 573 K. Single crystals were obtained by slow evaporation of a solution of the title compound in EtOH/CHCl3 (1:2) at room temperature. 1H-NMR (CDCl3, 500.13 MHz): δ 1.55–1.69 (m, 6H, adamantane-H), 1.86 (s, 3H, adamantane-H), 1.96 (s, 6H, adamantane-H), 7.24–7.32 (m, 4H, Ar—H), 11.89 (br. s, 1H, NH). 13C-NMR (CDCl3, 125.76 MHz): δ 27.85, 35.14, 36.72, 38.85 (adamantane-C), 118.22, 127.16, 132.51, 137.99 (Ar—C), 158.17 (triazole C = N), 171.11 (triazole C = S). EI-MS m/z (Rel. Int.): 329 (M+, 100).
Experimental details
Carbon-bound hydrogen atoms were placed in calculated positions and were included in the refinement using the riding model approximation, with Uiso(H) set to 1.2Ueq(C). The position and Uiso of the nitrogen-bound hydrogen atom was freely refined.
Discussion
Various adamantane-based drugs have long been known as efficient medications for the control of several diseases [1, 2] . Amantadine [3], [4], [5], rimantadine [6] and tromantadine [7] are currently used as efficient antiviral drugs. Moreover, adamantane derivatives were also reported to exhibit marked anti-HIV [8], [9], [10], antibacterial [11], [12], [13], antimalarial [14], hypoglycemic [15, 16] , anti-inflammatory [17, 18] , and anticancer [19] activities. 1,2,4-Triazole derivatives were reported to possess significant anti-inflammatory [20, 21] and antibacterial [22] activities. The title compound was prepared as an adamantane-triazole hybrid derivative as potential bioactive agent [23]. The asymmetric unit of the title compound contains one independent molecule. Pairs of molecules pack in the crystal structure via one strong classical intermolecular hydrogen bond N2—H1N2⋯S1i. The D⋯A and H⋯A distances are 3.252(2) and 2.40(2) Å, respectively, and the D-H⋯A angle is 176(3)°. Symmetry code: (i) − x, − y + 1, − z.
Acknowledgement
The authors would like to extend their sincere appreciation to the Deanship of Scientific Research at King Saud University for funding this work through the Research Group Project No. RG-1435-062.
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About the article
Received: 2016-10-06
Accepted: 2017-03-15
Published Online: 2017-04-01
Published in Print: 2017-05-24
Citation Information: Zeitschrift für Kristallographie - New Crystal Structures, Volume 232, Issue 3, Pages 443–445, ISSN (Online) 2197-4578, ISSN (Print) 1433-7266, DOI: https://doi.org/10.1515/ncrs-2016-0309.
©2017 Mona M. Al-Shehri 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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