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Z. Kristallogr. NCS 2019; 234(3): 543–545
Mohammad Hayal Alotaibi*, Hanan A. Mohamed, Bakr F. Abdel-Wahab, Amany S. Hegazy,Benson M. Kariuki and Gamal A. El-Hiti*
Crystal structure of 5-(5-(4-chlorophenyl)-1-phenyl-1H-pyrazol-3-yl)-N-phenyl-2-amine,C23H16ClN5O
https://doi.org/10.1515/ncrs-2018-0546Received December 1, 2018; accepted February 9, 2019; availableonline March 4, 2019
*Corresponding authors: Mohammad Hayal Alotaibi, NationalCenter for Petrochemicals Technology, King Abdulaziz City forScience and Technology, P.O. Box 6086, Riyadh 11442, SaudiArabia, e-mail: [email protected]; and Gamal A. El-Hiti,Department of Optometry, College of Applied Medical Sciences,King Saud University, P.O. Box 10219, Riyadh 11433, Saudi Arabia,e-mail: [email protected] A. Mohamed and Bakr F. Abdel-Wahab: Department ofChemistry, College of Science and Humanities, Shaqra Univer-sity, Duwadimi, Saudi Arabia; and Applied Organic ChemistryDepartment, National Research Centre, Dokki, Giza, EgyptAmany S. Hegazy and Benson M. Kariuki: School of Chemistry,Cardiff University, Main Building, Park Place, Cardiff CF10 3AT, UK
V = 4028.1(4) Å3, Z = 8, Rgt(F)=0.0748, wRref(F2)=0.2274,T = 296(2) K.
The asymmetric unit of the title crystal structure containingtwo molecules is shown in the figure. Tables 1 and 2 con-tain details on crystal structure and measurement conditionsand a list of the atoms including atomic coordinates anddisplacement parameters.
Source of materialThe title compound was synthesized from treatmentof 2-(5-(4-chlorophenyl)-1-phenyl-1H-pyrazole-3-carbonyl)-N-phenylhydrazinecarbothioamide with anhydrous sodiumacetate in boiling ethanol for 5 h. The solid obtained on cool-ing the reaction mixture was filtered, washed with ethanol,dried and crystallized from dimethylformamide to give color-less crystals (63%) of the title compound, Mp. 238−240 °C.
Experimental detailsH atoms were positioned geometrically and refined using ariding model. U iso(H) for aromatic and N—H hydrogens wereset to 1.2 times Ueq for the atoms they are bonded to. Aro-matic C—Hbondswere fixed at 0.93 Å andN—Hat 0.86 Å. Theweakly diffracting crystal yielded a wR2 factor slightly largerthan 20%. Nevertheless the data weren’t cut, as the strongestof them may provide some information.
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Alotaibi et al.: C23H16ClN5O | 545
CommentHeterocycles containing the 1,3,4-oxadiazol-2-amine moietyshow different biological activities and act as anticancer andantiproliferative agents [5–8]. Also, the pyrazole ring systemis the core of a number of drugs such as celecoxib, fezolamideand difenamizole [9–11].
The asymmetric unit comprises two independentmolecules (see the figure). Themolecule consists of five rings:phenyl (R1), oxadiazolyl (R2), pyraxolyl (R3), chlorophenyl(R4) and a second phenyl (R5) ring linked to R3. The twistangles between the planes of pairs of linked rings R1–R2,R2–R3, R3–R4, R3–R5 are 17.54(11), 11.94(17), 43.54(12) and52.49(10)° respectively for the first molecule (C1—C23) and6.81(12), 18.80(13), 43.10(11) and 7844(11)° respectively for thesecondmolecule (C24—C46).Weak intramolecular contacts ofC—H· · ·N type involving phenyl and oxadiazolyl rings occur.R22(9) rings due to N—H· · ·N and C—H· · ·N interactionsbetween neighbouring molecules lead to the formation ofribbons parallel to [100].
Acknowledgements: Mohammad Hayal Alotaibi thanksKing Abdulaziz City for Science and Technology (KACST),Saudi Arabia for financial support (award No. 020-0180).
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