1,5-Bis(4-fluorophenyl)penta-1,4-dien-3-
one
Ray J. Butcher,
a
Jerry P. Jasinski,
b
* B. K. Sarojini,
c
H. S.
Yathirajan,
d
S Bindya
d
and B. Narayana
e
a
Department of Chemistry, Howard University, 525 College Street NW, Washington,
DC 20059, USA,
b
Department of Chemistry, Keene State College, 229 Main Street,
Keene, NH 03435-2001, USA,
c
Department of Chemistry, P. A. College of
Engineering, Nadupadavu, Mangalore 574 153, India,
d
Department of Studies in
Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and
e
Department of Chemistry, Mangalore Universi ty, Mangalagangotri 574 199, India
Correspondence e-mail: jjasinski@keene.edu
Received 20 May 2007; accepted 28 May 2007
Key indicators: single-crystal X-ray study; T = 173 K; mean (C–C) = 0.004 A
˚
;
disorder in main residue; R factor = 0.094; wR factor = 0.275; data-to-parameter
ratio = 18.6.
The title compound, C
17
H
12
FO, a derivative of the anti-
oxidant, antibacterial and anti-inflammatory compound
curcumin, crystallizes with three independent molecules (A,
B and C) in the asymmetric unit. Molecule C is found to have
whole-molecule disorder with an approximate 2:1 ratio of
occupancies. The mean planes of the two 4-fluorophenyl
groups in A, B and C form dihedral angles of 54.8 (2), 54.3 (1)
and 52.4 (8)
, respectively. The angles between the mean plane
of the penta-1,4-dien-3-one group and those of the two 4-
fluorophenyl rings are 26.9 (3) and 33.7 (7)
in molecule A,
25.3 (1) and 34.2 (6)
in B, and 28.0 (9) and 30.8 (1)
in C.The
crystal structure is stabilized by intermolecular hydrogen
bonds.
Related literature
For the synthesis of the title compound, see: Furniss et al.
(1989). For biological activity of the title compound and
curcumin, see: Reksohadiprodjo et al. (2004) and Filler &
Kabayashi (1992), respectively. For related structures, see:
Harrison et al. (2006); Butcher et al. (2006).
Experimental
Crystal data
C
17
H
12
F
2
O
M
r
= 270.27
Monoclinic, Cc
a = 90.019 (14) A
˚
b = 5.8228 (9) A
˚
c = 7.5301 (12) A
˚
= 90.868 (4)
V = 3946.5 (11) A
˚
3
Z =12
Mo K radiation
= 0.10 mm
1
T = 173 K
0.50 0.25 0.15 mm
Data collection
Bruker SMART CCD area-detector
diffractometer
Absorption correction: none
5194 measured reflections
5194 independent reflections
3837 reflections with I >2(I)
R
int
= 0.035
Refinement
R[F
2
>2(F
2
)] = 0.094
wR(F
2
) = 0.275
S = 1.06
5194 reflections
541 parameters
50 restraints
H-atom parameters constrained
max
= 0.58 e A
˚
3
min
= 0.33 e A
˚
3
Table 1
Hydrogen-bond geometry (A
˚
,
).
D—HAD—H HADAD—HA
C7CA—H7CAO1CB
i
0.95 2.38 3.260 (8) 153
C11D—H11DO1CA
i
0.95 2.50 3.379 (9) 154
Symmetry code: (i) x; y þ 1; z.
Data collection: SMART (Bruker, 2000); cell refinement: SMART;
data reduction: SAINT (Bruker, 2006); program(s) used to solve
structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine
structure: SHELXL97 (Sheldrick, 1997); molecular graphics:
ORTEP-3 (Farrugia, 1997); software used to prepare material for
publication: SHELXTL (Bruker, 2000).
BKS thanks the All India Council for Technical Education
(AICTE, Government of India) for financial assistance
through the Career Award for Young Teachers Scheme. SB
thanks the Un iversity of Mysore for use of their research
facilities. RJB acknowledges the Laboratory for the Structure
of Matter at the Naval Research Laboratory for access to their
diffractometer.
Supplementary data and figures for this paper are available from the
IUCr electronic archives (Reference: TK2156).
References
Bruker (2000). SMART and SHELXTL (Version 6.10). Bruker AXS Inc.,
Madison, Wisconsin, USA.
Bruker (2006). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Butcher, R. J., Yathirajan, H. S., Sarojini, B. K., Narayana, B. & Vijaya Raj,
K. K. (2006). Acta Cryst. E62, o1973–o1975.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Filler, R. & Kabayashi, Y. (1992). Biomedicinal Aspects of Fluorine Chemistry.
Amsterdam: Elsevier.
Furniss, B. S., Hannaford, A. J., Smith, P. W. G. & Tatchell, A. R. (1989).
Editors. Vogel’s Textbook of Practical Organic Chemistry, 5th ed., p. 1033.
London: Longman Group UK Ltd.
organic compounds
Acta Cryst. (2007). E63, o3213–o3214 doi:10.1107/S1600536807026116 # 2007 International Union of Crystallography o3213
Acta Crystallographica Section E
Structure Reports
Online
ISSN 1600-5368
Harrison, W. T. A., Sarojini, B. K., Vijaya Raj, K. K., Yathirajan, H. S. &
Narayana, B. (2006). Acta Cryst. E62, o1522–o1523.
Reksohadiprodjo, M. S., Timmerman, H., Sardjiman, H., Margono, S. A.,
Martono, S., Sugiyanto, S., Hakim, L., Nurlaila, L., Hakim, A. R.,
Puspitasari, I., Nurrochmad, A., Purwantiningsih, A., Oetari, A. & Yuwono,
T. (2004). US Patent No. 6 777 447 B2.
Sheldrick, G. M. (1990). Acta Cryst. A46, 467–473.
Sheldrick, G. M. (1997). SHELXL97. University of Go
¨
ttingen, Germany.
organic compounds
o3214 Butcher et al.
C
17
H
12
F
2
O Acta Cryst. (2007). E63, o3213–o3214
supplementary materials
supplementary materials
sup-1
Acta Cryst. (2007). E63, o3213-o3214 [ doi:10.1107/S1600536807026116 ]
1,5-Bis(4-fluorophenyl)penta-1,4-dien-3-one
R. J. Butcher, J. P. Jasinski, B. K. Sarojini, H. S. Yathirajan, S. Bindya and B. Narayana
Comment
The title compound, (I), is a biologically active compound. Derivatives of dibenzylidene acetone, cyclopentanone and
cyclohexanone derivatives exhibit potent anti-inflammatory, anti-bacterial and anti-oxidant activity. Certain derivat-
ives inhibit glutathione S-transferace (GST) but do not irritate the gastrointestinal tract. Curcumin, 1,5-di(4-hydroxy-3-
methoxyphenyl)penta-1,4-dien-3-one, is a major constituent of turmeric, the commonly used spice. It has been widely used
as an anti-inflammatory, anti-bacterial, anti-oxidant, anti-hepatotoxic, hypocholesterolanemia, anti-cyclooxygenase, anti-
cancer and radical scavenger agent. It is reported that curcumin is non-toxic at high doses and substitution on the aromatic
rings with electron-donating and -withdrawing groups increases anti-inflammatory activity (Reksohadiprodjo et al., 2004).
Recently, fluorinated organic compounds have attracted attention due to the ability of fluorine to act as a polar-hydrogen or
hydroxyl mimic. Therefore, substitution of hydrogen by fluorine has been a strategy in designing molecules for biological
activity studies (Filler & Kabayashi, 1992). Most recently, a redetermination of 1,5-bis(4-methoxyphenyl)penta-1,4-dien-3-
one at 120 (2) K (Harrison et al., 2006) and the crystal structure of 1,5-bis(4-chlorophenyl)penta-1,4-dien-3-one have been
reported (Butcher et al., 2006).
Experimental
The title compound was synthesized according to the method reported in the literature (Furniss et al., 1989). A solution of of
NaOH (25 g) in water (250 ml) and ethanol (200 ml) was placed in a 500 ml bolt head flask fitted with a mechanical stirrer.
The flask was immersed in a water bath and the temperature of the solution was maintained at 393–398 K. The solution
was stirred vigorously and to it was added one half of a previously prepared mixture of 4-fluorobenzaldehyde (31 g, 0.25
mol) and acetone (7.3 g, 0.125 mol). A flocculent precipitate formed within 2–3 minutes. After 15 minutes, the remainder
of the aldehyde-acetone mixture was added and the stirring was continued for a further 30 min. The crude product obtained
was filtered and washed with cold water to eliminate the alkali as completely as possible. The compound was purified from
ethanol (yield:80%). The crystal growth was done in acetone:toluene (1:1) solvent by the slow evaporation technique; m.p.
383–387 K. Analysis for C
17
H
12
FO: Found (Calculated): C: 75.44 (75.55); H: 4.42 (4.48).
Refinement
The H atoms were included in the riding model approximation with C—H = 0.95 Å, and with U
iso
(H) = 1.17–1.21U
eq
(C).
Figures
Fig. 1. Molecular structure of molecule A for C
17
H
12
FO, (I), showing atom labeling and 50%
probability displacement ellipsoids.
supplementary materials
sup-2
Fig. 2. Packing diagram of C
17
H
12
FO viewed down the a axis.
Fig. 3. The formation of the title compound.
1,5-Bis(4-fluorophenyl)penta-1,4-dien-3-one
Crystal data
C
17
H
12
F
2
O
F
000
= 1680
M
r
= 270.27
D
x
= 1.365 Mg m
−3
Monoclinic, Cc
Mo Kα radiation
λ = 0.71073 Å
a = 90.019 (14) Å
Cell parameters from 4065 reflections
b = 5.8228 (9) Å
θ = 2.7–28.1º
c = 7.5301 (12) Å
µ = 0.10 mm
−1
β = 90.868 (4)º
T = 173 K
V = 3946.5 (11) Å
3
Chunk, colorless
Z = 12
0.50 × 0.25 × 0.15 mm
Data collection
Bruker SMART CCD area-detector
diffractometer
R
int
= 0.035
φ and ω scans
θ
max
= 29.1º
Absorption correction: none
θ
min
= 0.9º
5194 measured reflections
h = −122→122
5194 independent reflections
k = 0→7
3837 reflections with I > 2σ(I) l = 0→10
Refinement
Refinement on F
2
H-atom parameters constrained
Least-squares matrix: full
w = 1/[σ
2
(F
o
2
) + (0.144P)
2
+ 6.6257P]
where P = (F
o
2
+ 2F
c
2
)/3
R[F
2
> 2σ(F
2
)] = 0.094
(Δ/σ)
max
= 0.035
