Abstract
 C15H9FN4S, orthorhombic, Pna21 (no. 33), a = 18.9361(2) Å, b = 11.5248(1) Å, c = 6.0142(1) Å, V = 1312.52(3) Å3, Z = 4, R
 gt
 (F) = 0.0263, wR
 ref
 (F
 2
 ) = 0.0706, T = 100 K.</jats:p

Al-Alshaikh, M. A.

El-Emam, A. Ali

García-Granda, Santiago

Ghabbour, H. A.

Said Mohammed Abdelbaky, Mohammed

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. PRG-1436–23. We also acknowledge the financial support from Spanish Ministerio de Economía y Competitividad (MINECO-13-MAT2013–40950-R, FPI grant BES-2011–046948 to MSM-A

Repositorio Institucional de la Universidad de Oviedo

Z. Kristallogr. NCS 2016; 231(2): 661–663Open AccessMonirah A. Al-Alshaikh, Hazem A. Ghabbour, Mohammed S. M. Abdelbaky,Santiago García-Granda and Ali A. El-Emam*Crystal structure of 6-(2-fluorophenyl)-3-phenyl-[1,2,4]-triazolo[3,4-b][1,3,4]thiadiazole, C15H9FN4SDOI 10.1515/ncrs-2015-0236Received January 25, 2016; accepted February 9, 2016; availableonline February 26, 2016AbstractC15H9FN4S, orthorhombic, Pna21 (no. 33), a= 18.9361(2) Å,b= 11.5248(1) Å, c= 6.0142(1) Å, V = 1312.52(3) Å3, Z= 4,Rgt(F)=0.0263, wRref(F2)=0.0706, T= 100 K.CCDC no.: 1416454The crystal structure is shown in the gure. Tables 1–3contain details of the measurement method and a list ofthe atoms including atomic coordinates and displacementparameters.*Corresponding author: Ali A. El-Emam, Department ofPharmaceutical Chemistry, College of Pharmacy, King SaudUniversity, P. O. Box 2457, Riyadh 11451, Saudi Arabia,e-mail: elemam5@hotmail.comMonirah A. Al-Alshaikh: Department of Chemistry, College ofSciences, King Saud University, Riyadh 11451, Saudi ArabiaHazem A. Ghabbour: Department of Pharmaceutical Chemistry,College of Pharmacy, King Saud University, P. O. Box 2457, Riyadh11451, Saudi Arabia; and Department of Medicinal Chemistry,Faculty of Pharmacy, Mansoura University, Mansoura 35516,EgyptMohammed S. M. Abdelbaky and Santiago García-Granda:Departamento de Química Física Analítica, Facultad de Química,Universidad de Oviedo – CINN, C/Julán Clavería, 8, 33006 Oviedo,(Asturias), SpainTable 1: Data collection and handling.Crystal: Colourless, prism,size 0.1467×0.1714×0.3504 mmWavelength: Cu Kα radiation (1.54184 Å)µ: 22.9 cm−1Diractometer, scan mode: Xcalibur, Ruby, Gemini, ω scans2θmax: 140.94°N(hkl)measured, N(hkl)unique: 6872, 2510Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 2044N(param)rened: 190Programs: CrysAlisPRO [16], SHELX [17]Table 2: Fractional atomic coordinates and isotropic or equivalentisotropic displacement parameters (Å2).Atom Site x y z UisoH(12) 4a 0.2635 0.6295 −0.5280 0.042H(5) 4a 0.5152 0.0662 0.9684 0.041H(13) 4a 0.3812 0.6383 −0.6289 0.047H(15) 4a 0.4320 0.4358 −0.1120 0.037H(2) 4a 0.4707 0.2752 0.3255 0.036H(6) 4a 0.4001 0.1159 0.8790 0.036H(3) 4a 0.5853 0.2271 0.4230 0.042H(4) 4a 0.6076 0.1239 0.7454 0.040H(14) 4a 0.4649 0.5392 −0.4229 0.047Source of materialA mixture of 4-amino-5-phenyl-4H-1,2,4-triazole-3-thiol(1.92 g, 0.01 mol), 2-uorobenzoyl chloride (1.40 g, 0.01 mol)and phosphorous oxychloride (10 mL) was heated underreux for four hours. On cooling, the reaction mixturewas cautiously poured onto crushed ice (50 gm) and theprecipitated solid productwasltered,washedwith saturatedsodium hydrogen carbonate solution and then with water,dried, crystallized fromethanol to yield 2.16 g (73%) of the titlecompound. M.p. 517–519 K. Colourless prismatic crystals wereobtained by slow evaporation of chloroform-ethanol solution(1:1) at room temperature. 1H NMR (CDCl3, 500.13 MHz): δ7.16–7.33 (m, 6H, aromatic-H), 7.55–7.77 (m, 3H, aromatic-H).13C NMR (CDCl3, 125.76 MHz): δ= 115.11, 120.73, 124.27, 127.54,127.61, 127.77, 133.45, 133.52, 144.57, 158.43 (aromatic-C), 160.05(C-3), 160.46 (C-8), 163.96 (C-6).© 2016 Monirah A. Al-Alshaikh et al., published by De Gruyter.This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.Brought to you by | Instituto Feijoo de EstudiosAuthenticatedDownload Date | 3/6/17 9:30 AM662 | Al-Alshaikh et al.: C15H9FN4STable 3: Fractional coordinates and atomic displacement parameters (Å2).Atom Site x y z U11 U22 U33 U12 U13 U23S(1) 4a 0.22196(2) 0.39409(3) 0.17939(9) 0.0203(2) 0.0243(2) 0.0278(2) 0.0004(1) −0.0020(2) −0.0002(2)F(1) 4a 0.20979(6) 0.5248(1) −0.2014(2) 0.0355(6) 0.0347(6) 0.0354(7) 0.0103(5) −0.0101(5) −0.0024(5)N(3) 4a 0.32725(7) 0.2993(1) 0.3665(3) 0.0216(7) 0.0203(6) 0.0201(8) −0.0016(6) 0.0010(7) 0.0000(6)N(4) 4a 0.35789(7) 0.3513(1) 0.1858(3) 0.0241(7) 0.0211(6) 0.0184(7) −0.0016(5) 0.0000(8) 0.0000(7)N(1) 4a 0.29497(7) 0.2115(1) 0.6688(3) 0.0273(7) 0.0224(6) 0.0250(8) −0.0034(5) 0.0043(8) 0.0000(7)N(2) 4a 0.23441(8) 0.2597(1) 0.5748(3) 0.0275(8) 0.0250(7) 0.0252(9) −0.0038(6) 0.0004(8) −0.0001(7)C(12) 4a 0.2976(1) 0.5912(2) −0.4444(4) 0.062(1) 0.0189(8) 0.023(1) 0.0032(9) −0.014(1) −0.0028(8)C(10) 4a 0.3273(1) 0.4703(1) −0.1265(3) 0.031(1) 0.0186(7) 0.021(1) −0.0038(7) −0.0054(8) −0.0013(7)C(5) 4a 0.5062(1) 0.1091(2) 0.8405(4) 0.045(1) 0.030(1) 0.029(1) 0.0049(8) −0.013(1) 0.0051(8)C(13) 4a 0.3675(1) 0.5957(2) −0.5047(4) 0.068(2) 0.027(1) 0.023(1) −0.015(1) −0.003(1) 0.0035(8)C(15) 4a 0.3979(1) 0.4750(2) −0.1939(4) 0.032(1) 0.034(1) 0.026(1) −0.0076(8) −0.0042(8) 0.0050(8)C(11) 4a 0.2789(1) 0.5289(2) −0.2584(4) 0.037(1) 0.0195(8) 0.027(1) 0.0018(7) −0.0095(9) −0.0057(7)C(7) 4a 0.3502(1) 0.2355(2) 0.5453(3) 0.030(1) 0.0175(8) 0.0209(9) −0.0016(7) −0.0012(8) 0.0001(7)C(2) 4a 0.4793(1) 0.2341(2) 0.4558(4) 0.028(1) 0.0327(9) 0.030(1) 0.0030(8) −0.0001(9) 0.0091(8)C(8) 4a 0.25608(9) 0.3114(2) 0.3954(3) 0.0207(8) 0.0206(8) 0.028(1) −0.0015(7) 0.0002(8) −0.0028(8)C(6) 4a 0.4371(1) 0.1384(2) 0.7867(4) 0.036(1) 0.0278(9) 0.026(1) −0.0001(8) 0.0013(9) 0.0035(8)C(1) 4a 0.4233(1) 0.2018(1) 0.5933(4) 0.0277(9) 0.0201(8) 0.0250(9) −0.0004(7) −0.0024(8) −0.0022(7)C(3) 4a 0.5480(1) 0.2048(2) 0.5141(4) 0.026(1) 0.038(1) 0.040(1) 0.0023(8) −0.001(1) 0.004(1)C(4) 4a 0.5615(1) 0.1427(2) 0.7067(4) 0.0296(9) 0.0313(9) 0.040(1) 0.0044(7) −0.010(1) −0.0024(9)C(14) 4a 0.4177(1) 0.5370(2) −0.3806(4) 0.045(1) 0.044(1) 0.030(1) −0.016(1) 0.004(1) 0.0048(9)C(9) 4a 0.30898(9) 0.4043(1) 0.0730(3) 0.0220(9) 0.0191(7) 0.024(1) −0.0004(6) −0.0004(8) −0.0031(7)Experimental detailsCell renement and data reduction were carried out byCrysAlis PRO [16]. The coordinates of the aromatic H atomswere idealized and rened using a riding model (AFIX 43option of the SHELX program [17]).Discussion1,2,4-Triazole derivatives and their fused heterocyclic ana-logues are well known for their dierent biological activitiesover 30 years ago, and 1,2,4-triazole rings have been incor-porated into ligands used in coordination compounds andpolymers. Thus, various 1,2,4-triazole derivatives and theirN-bridged heterocyclic analogues have been extensively stud-ied [1–6]. Several 3,6-disubstituted[1,2,4]triazolo[3,4-b][1,3,4]thiadiazoles were reported to exhibit signicant antibacte-rial [7–10], pesticidal [11], anticancer [12], anti-inammatory,analgesic and anti-oxidant activities [13]. In continuationto a previous interest in the chemical synthesis of [1,2,4]-triazolo[3,4-b][1,3,4]thiadiazole derivatives [14, 15], we reportherein the synthesis and the crystal structure of the titlecompound as potential bioactive agent.One independent molecule comprises the asym-metric unit. The compound is nearly planer, with re-spect to the [1,2,4]-triazolo[3,4-b][1,3,4]thiadiazole system(N1/N2/C8/S1/C9/N4/N3/C7), the uorophenyl ring (C10—C15) form dihedral angles of 2.55 (6)° and the phenyl ring(C1—C6) form dihedral angles of 3.83 (3)°. In the crystalstructure, the packing is stabilized by one non-classicalintermolecular hydrogen bond, of which the N1 acts ashydrogen bond acceptor and the C12 acts as hydrogen bonddonor. The distance of the interaction between C12—H12· · ·N1is 2.33 Å and the angle is 161°.Acknowledgements: The authors would like to extend theirsincere appreciation to the Deanship of Scientic Research atKing Saud University for funding this work through the Re-search Group Project No. PRG-1436–23. We also acknowledgethe nancial support from Spanish Ministerio de Economíay Competitividad (MINECO-13-MAT2013–40950-R, FPI grantBES-2011–046948 to MSM-A).References1. Chai, X.; Zhang, J.; Yu, S.; Hu, H.; Zou, Y.; Zhao, Q.; Dan, Z.;Zhang, D.; Wu, Q.: Design, synthesis, and biological evaluationof novel 1-(1H-1,2,4-triazole-1-yl)-2-(2,4-difluorophenyl)-3-substituted benzylamino-2-propanols. Bioorg. Med. Chem.Lett. 19 (2009) 1811–1814.2. El-Emam, A. A.; Ibrahim, T. M.: Synthesis, anti-inflammatoryand analgesic activity of certain 3-(1-adamantyl)-4-substituted-5-mercapto-1,2,4-triazole derivatives. Arzneim.-Forsch./DrugRes. 41 (1991) 1260–1264.3. Aboelmagd, A.; Ali, I. A. I.; Salem, E. M. S.; Abdel-Razik, M.:Synthesis and antifungal activity of some s-mercaptotria-zolobenzothiazolyl amino acid derivatives. Eur. J. Med. Chem.60 (2013) 503–511.Brought to you by | Instituto Feijoo de EstudiosAuthenticatedDownload Date | 3/6/17 9:30 AMAl-Alshaikh et al.: C15H9FN4S | 6634. El-Emam, A. A.; Al-Tamimi, A.-M. S.; Al-Omar, M. A.;Al-Rashood, K. A.; Habib, E. E.: Synthesis and antimicrobialactivity of novel 5-(1-adamantyl)-2-aminomethyl-4-substituted-1,2,4-triazoline-3-thiones. Eur. J. Med. Chem. 68 (2013)96–102.5. Luo, Y.; Zhang, S.; Liu, Z.-J.; Chen, W.; Fu, J.; Zeng, Q.-F.:Synthesis and antimicrobical evaluation of a novel classof 1,3,4-thiadiazole: derivatives bearing 1,2,4-triazolo[1,5-a]pyrimidine moiety. Eur. J. Med. Chem. 64 (2013) 54–61.6. Plech, T.; Wujec, M.; Kosikowska, U.; Malm, A.; Kaproń, B.:Studies on the synthesis and antibacterial activity of 3,6-disubstituted 1,2,4-triazolo[3,4-b]1,3,4-thiadiazoles. Eur. J.Med. Chem. 47 (2012) 580–584.7. Eweiss, N. F.; Bahajaj, A. A.: Synthesis of heterocycles. Part VII.Synthesis and antimicrobial activity of some 7H-s-triazolo[3,4-b][1,3,4]thiadiazine and s-triazolo[3,4-b][1,3,4]thiadiazolederivatives. J. Heterocycl. Chem. 24 (1987) 1173–1181.8. Kotaiah, Y.; Nagaraju, K.; Harikrishna, N.; Rao, C. V.; Yamini, L.;Vijjulatha, M.: Synthesis, docking and evaluation of antioxidantand antimicrobial activities of novel 1,2,4-triazolo[3,4-b][1,3,4]thiadiazol-6-yl)selenopheno[2,3-d]pyrimidines. Eur. J. Med.Chem. 75 (2014) 195–202.9. Swamy, S. N.; Basappa; Priya, B. S.; Prabhuswamy, B.;Doreswamy, B. H.; Shahidhara, J. S.; Rangappa, K. S.:Synthesis of pharmaceutically important condensedheterocyclic 4,6-disubstituted-1,2,4-triazolo-1,3,4-thiadiazolederivatives as antimicrobials. Eur. J. Med. Chem. 41 (2006)531–538.10. Mathew, V.; Keshavayya, J.; Vaidya, V. P.: Heterocyclicsystem containing bridged nitrogen atom: synthesis andpharmacological activities of some substituted 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles. Eur. J. Med. Chem. 41 (2006)1048–1058.11. Chaturvedi, B.; Tiwari, N.; Nirupama, N.: A convenient synthesisof 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles as potentialpesticides. Agri. Biol. Chem. 52 (1988) 1229–1232.12. Khan, I.; Zaib, S.; Ibrar, A.; Rama, N. S.; Simpson, J.; Iqbal, J.:Synthesis, crystal structure and biological evaluation ofsome novel 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles and 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazines. Eur. J. Med. Chem. 78 (2014)167–177.13. Chidananda, N; Poojary, B.; Sumangala, V.; Kumari, N. S.;Shetty, P.; Arulmoli, T.: Facile synthesis, characterizationand pharmacological activities of 3,6-disubstituted 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles and 5,6-dihydro-3,6-disubstituted-1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles. Eur. J.Med. Chem. 51 (2012) 124–136.14. Al-Abdullah, E. S.; Shehata, I. 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Zeitschrift für Kristallographie - New Crystal Structures

Crystal structure of 6-(2-fluorophenyl)-3-phenyl-[1,2,4]-triazolo[3,4-b][1,3,4]thiadiazole, C15H9FN4S

Monirah A. Al-Alshaikh

Hazem A. Ghabbour

Mohammed S. M. Abdelbaky

Santiago García-Granda

Ali A. El-Emam

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Crystal structure of 6-(2-fluorophenyl)-3-phenyl-[1,2,4]-triazolo[3,4-b][1,3,4]thiadiazole, C15H9FN4S

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Crystal structure of 6-(2-fluorophenyl)-3-phenyl-[1,2,4]-triazolo[3,4-b][1,3,4]thiadiazole, C15H9FN4S

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