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Crystals 2012, 2(3), 1108-1115; doi:10.3390/cryst2031108
Article

Synthesis, Characterization and Crystal Structures of 3,5-Bis(4-fluorophenyl)-4,5-dihydro-1H-pyrazole-1-carboxamide and 3,5-Bis(4-fluorophenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide

1,* , 1
,
2
,
2
 and
3
1 Department of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA 2 Department of Studies in Chemistry, Mangalore University, Mangalagangotri-574 199, India 3 Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore-570 006, India
* Author to whom correspondence should be addressed.
Received: 28 June 2012 / Revised: 19 July 2012 / Accepted: 24 July 2012 / Published: 15 August 2012
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Abstract

Two new pyrazoline derivatives, 3,5-bis(4-fluorophenyl)-4,5-dihydropyrazole-1-carboxamide (1) and 3,5-bis(4-fluorophenyl)-4,5-dihydropyrazole-1-carbothioamide (2), were synthesized by reacting 4,4'-difluoro chalcone with semicarbazide hydrochloride and thiosemicarbazide in ethanolic sodium hydroxide solution. Both the compounds were confirmed by single crystal X-ray diffraction data and supported by IR, NMR, and mass spectral data. In 1, crystal packing is stabilized by N–H…O hydrogen bonds and weak N–H...N, N–H…F and C–H…F intermolecular interactions. In 2, only weak N–H…F and N–H…S intermolecular interactions are observed. Crystal data: C16H13F2N3O, (1), Mr = 301.29, monoclinic, C2/c, a = 17.6219(6) Å, b = 10.8735(3) Å, c = 15.3216(5) Å, β = 102.864(3)°, V = 2862.11(16) Å3, Z = 8, T = 173 K, R(F) = 0.0511, wR(F2) = 0.1333; C16H13F2N3S, (2), Mr = 317.35, monoclinic, P21/c, a = 14.339(2) Å, b = 11.1478(17) Å, c = 9.541(2)(5) Å, β = 107.007(18)°, V = 1458.5(5) Å3, Z = 4, T = 173 K, R(F) = 0.0413, wR(F2) = 0.0959.
Keywords: pyrazoline derivatives; X-ray crystal structure; hydrogen bonds; weak intermolecular interactions pyrazoline derivatives; X-ray crystal structure; hydrogen bonds; weak intermolecular interactions
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Jasinski, J.P.; Golen, J.A.; Samshuddin, S.; Narayana, B.; Yathirajan, H.S. Synthesis, Characterization and Crystal Structures of 3,5-Bis(4-fluorophenyl)-4,5-dihydro-1H-pyrazole-1-carboxamide and 3,5-Bis(4-fluorophenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide. Crystals 2012, 2, 1108-1115.

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