Asian Journal of Chemistry; Vol. 26, No. 24 (2014), 8593-8595
ASIAN JOURNAL OF CHEMISTRY
Synthesis and Crystal Structure of [α-(2,4-Difluorophenyl)-α-(1H-1,2,4-
triazole-1-ylmethyl)-1H-1,2,4-triazole-1-ethanol]Cu(II) Complex
1,2
2,*
YONGFEN WANG and CHUANZHOU BIAN
1
2
College of Life Science, ShanXi Normal University, Xi'an 710062, P.R. China
Academy of Bioengineering, Henan University of Animal Husbandry and Economy, Zhengzhou 450011, P.R. China
*
Corresponding author: E-mail: jyzhang2004@126.com
Received: 5 July 2014;
Accepted: 10 October 2014;
Published online: 1 December 2014;
AJC-16411
A novel complex of copper(II) was prepared by reaction of CuCl and fluconazole at reflux in water and tetrahydrofuran. Its structure was
2
determined by single crystal X-ray diffraction analysis. The crystals are monoclinic space group C2/c with a = 23.490(2), b = 9.4719(9),
3
3
-1
c = 19.8459(18) Å, α = 90.00, β = 123.639(2), γ = 90.00°, V = 3676.2(6) Å , Z = 4, F(000) = 1676, Dc = 1.480 g/cm , µ = 0.815 mm , the
final R = 0.0526 and wR = 0.1688. A total of 8828 reflections were collected, of which 3244 were independent (Rint = 0.0344).
Keywords: Fluconazole, Copper complex, Synthesis, Crystal structure.
3
1
1
23.639(2), γ = 90.00°, V = 3676.2(6) Å , Z = 14, F(000) =
INTRODUCTION
3
676, Dc = 1.480 g/cm . The absorption coefficient µ = 0.815
Fluconazole [α-(2,4-difluorophenyl)-α-(1H-1,2,4-triazole-
-ylmethyl)-1H-1,2,4- triazole-1-ethanol] is a triazole antifungal
-1
mm . The final R
1
= 0.0526 (> 2σ(I)) and wR = 0.1688. A
total of 8828 reflections were collected, of which 3244 were
independent (Rint = 0.0344). The structure was solved by direct
2
1
agent which is used in the treatment and prevention of superficial
1
-5
and systemic fungal infections such as or Opharyngeal
candidiasis and Cryptococcal meningitis inAIDS. Fluconazole
can inhibit endogenous respiration, interact with membrane
phospholipids, inhibit the transformation of yeasts to mycelial
forms. In addition, it may also inhibit purine uptake and impair
triglyceride and/or phospholipid biosynthesis. This compound
belongs to the phenylpropylamines containing a phenyl-
propylamine moiety, which consists of a phenyl group substi-
tuted at the third carbon by an propan-1-amine. In order to
improve the bioavailability or treatment effect and develop
new applications for fluconazole, metal complex of it has been
extensively investigated in our group. In this paper, as a
contribution in this filed, we report here the crystal structure
of the complex of fluconazole with copper.
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methods with SHELXS-97 and refined by the full-matrix least
2
7
squares method on F data using SHELXL-97 . The empirical
absorption corrections were applied to all intensity data. H
atom of N-H was initially located in a difference fourier map
and were refined with the restraint Uiso (H) = 1.2 Ueq (N).
Other H atoms were positioned geometrically and refined using
a riding model, with d (C-H) = 0.93-0.98 Å and Uiso (H) = 1.2
Ueq (C) or 1.5 Ueq (C-methyl). The final full-matrix least
squares refinement gave 0.0392 and wR = 0.0928.
Synthesis: To a solution of 2,4-difluoro-bromobenzene
(
0.10 mol) in THF, metal Mg (0.11 mol) and KI (catalyst dosage)
were added. The mixture was stirred at 50 °C for 2 h and then
,3-dichloropropan-2-one (0.10 mol) was added to the mixture
for another 3 h at room temperature. The solvent was removed.
The residue was dispersed in toluene and K CO was added
with stirring for 3 h at 90 °C. Then the mixture was filtered and
the toluene was removed in vacuum. The residue was recrys-
tallized to afford compound 4 (white powder).
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2
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EXPERIMENTAL
Determination of crystal structure: The crystal of title
compound with dimensions of 0.48 mm × 0.42 mm × 0.40 mm
was mounted on a Rigaku Saturn CCD area-detector diffrac-
RESULTS AND DISCUSSION
tometer with a graphite-monochromated MoK
α
radiation (λ =
0
.71073 Å) by using a phi and scan modes at 298 K in the
The complex was prepared by reaction of CuCl and fluco-
2
range of 2.1º ≤ θ ≤ 25º. The crystal belongs to monoclinic
system with space group C2/c and crystal parameters of a =
nazole at reflux in water and tetrahydrofuran. Then the mixture
was evaporated slowly affording colourless crystals suitable
for X-ray analysis.
2
3.490(2), b = 9.4719(9), c = 19.8459(18) Å, α = 90.00, β =