1-(4-Methylphenyl)-5-phenylpenta-2,4-
dien-1-one
Andreas Fischer,
a
* H. S. Yathirajan,
b
B. K. Sarojini,
c
S. Bindya
b
and B. Narayana
d
a
Inorganic Chemistry, School of Chemical Science and Engineering, Royal Institute of
Technology (KTH), 100 44 Stockholm, Sweden,
b
Department of Studies in
Chemistry, University of Mysore, Manasagangotri, Mysor e 570 006, India,
c
Department of Chemistry, P. A. College of Engineering, Nadupadavu, Mangalore
574 153, India, and
d
Department of Chemistry, Mangalore University,
Mangalagangotri 574 199, India
Correspondence e-mail: afischer@kth.se
Received 28 March 2007; accepted 24 April 2007
Key indicators: single-crystal X-ray study; T = 298 K; mean (C–C) = 0.004 A
˚
;
R factor = 0.068; wR factor = 0.162; data-to-parameter ratio = 14.3.
The title compound, C
18
H
16
O, features two conjugate double
bonds, both in E conformations. The molecule is essentially
planar: the dihedr al angle between the two phenyl groups is
9.4 (1)
.
Related literature
For related structures, see: Butcher et al. (2006), Yathirajan et
al. (2007), Harrison et al. (2006). For non-linear optical crys-
tals, see: Fichour et al. (1988), Cho et al. (1996), Goto et al.
(1991), Uchida et al. (1998), Tam et al. (1989), Indira et al.
(2002), Sarojini et al. (2006). For related literature, see: Fichou
et al. (1988); Furniss et al. (1989).
Experimental
Crystal data
C
18
H
16
O
M
r
= 248.33
Monoclinic, P2
1
=c
a = 7.7215 (12) A
˚
b = 10.6985 (12) A
˚
c = 17.331 (3) A
˚
= 99.550 (13)
V = 1411.9 (4) A
˚
3
Z =4
Mo K radiation
= 0.07 mm
1
T = 298 K
0.46 0.44 0.16 mm
Data collection
Bruker-Nonius KappaCCD
diffractometer
Absorption correction: none
12654 measured reflections
2465 independent reflections
1411 reflections with I >2(I)
R
int
= 0.083
Refinement
R[F
2
>2(F
2
)] = 0.068
wR(F
2
) = 0.162
S = 1.12
2465 reflections
172 parameters
H-atom parameters constrained
max
= 0.23 e A
˚
3
min
= 0.14 e A
˚
3
Data collection: COLLECT (Nonius, 1999); cell refinement:
DIRAX/LSQ (Duisenberg, 1992); data reduction: EVALCCD
(Duisenberg et al., 2003); program(s) used to solve structure:
SHELXS97 (Sheldrick, 1997); program(s) used to refine structure:
SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND
(Brandenburg, 2006); software used to prepare material for publi-
cation: publCIF (Westrip, 2007).
BKS thanks AICTE, Government of India, for financial
assistance through the Career Award for Young Teacher s
Scheme. SB thanks the University of Mysore for research
facilities. The Swedish Research Council (VR) is acknowl-
edged for providing funding for the single-crystal diffract-
ometer.
Supplementary data and figures for this paper are available from the
IUCr electronic archives (Reference: RZ2134).
References
Brandenburg, K. (2006). DIAMOND. Release 3.1d. Crystal Impact GbR,
Bonn, Germany.
Butcher, R. J., Yathirajan, H. S., Sarojini, B. K., Narayana, B. & Vijaya Raj,
K. K. (2006). Acta Cryst. E62, o1973–o1975.
Cho, B. R., Je, J. T., Kim, H. S., Jean, S. J., Song, O. K. & Wang, C. H. (1996).
Bull. Korean Chem. Soc. 17, 693–695.
Duisenberg, A. J. M. (1992). J. Appl. Cryst. 25, 92–96.
Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003).
J. Appl. Cryst. 36, 220–229.
Fichou, D., Watanabe, T., Takeda, T., Miyata, S., Goto, Y. & Nakayama, M.
(1988). Jpn J. Appl. Phys. 27, 429–430.
Furniss, B. S., Hannaford, A. J., Smith, P. W. G. & Tatchell, A. R. (1989).
Vogel’s Textbook of Practical Organic Chemistry, 5th ed, p. 1034. London:
Longman Group UK Ltd.
Goto, Y., Hayashi, A., Kimura, Y. & Nakayama, M. (1991). J. Cryst. Growth,
108, 688–698.
Harrison, W. T. A., Sarojini, B. K., Vijaya Raj, K. K., Yathirajan, H. S. &
Narayana, B. (2006). Acta Cryst. E62, o1522–o1523.
Indira, J., Karat, P. P. & Sarojini, B. K. (2002). J. Cryst. Growth, 242, 209–214.
Nonius (1999). COLLECT. Nonius B. V., Delft, The Netherlands.
Sarojini, B. K., Narayana, B., Ashalatha, B. V., Indira, J. & Lobo, K. J. (2006). J.
Cryst. Growth, 295, 54-59.
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of
Go
¨
ttingen, Germany.
Tam, W., Guerin, B., Calabrese, J. C. & Stevenson, S. H. (1989). Chem. Phys.
Lett. 154, 93–96.
Uchida, T., Kozawa, K., Sakai, T., Aoki, M., Yoguchi, H., Abduryim, A. &
Watanabe, Y. (1998). Mol. Cryst. Liq. Cryst. 315, 135–140.
Westrip (2007). publCIF. In preparation.
Yathirajan, H. S., Bindya, S., Mithun, A., Narayana, B. & Bolte, M. (2007).
Acta Cryst. E63, o61–o62.
organic compounds
o2832 # 2007 International Union of Crystallography doi:10.1107/S1600536807020582 Acta Cryst. (2007). E63, o2832
Acta Crystallographica Section E
Structure Reports
Online
ISSN 1600-5368
supplementary materials
supplementary materials
sup-1
Acta Cryst. (2007). E63, o2832 [ doi:10.1107/S1600536807020582 ]
1-(4-Methylphenyl)-5-phenylpenta-2,4-dien-1-one
A. Fischer, H. S. Yathirajan, B. K. Sarojini, S. Bindya and B. Narayana
Comment
The title compound, (I), C
18
H
16
O, 1-(4-methylphenyl)-5-phenylpenta-2,4-dien-1-one is an optically active molecule. The
present-day demand is for large and high quality ferroelectric, piezoelectric single crystals with minimum defects and in-
homogenities. The important goal of crystal growth is the improvement of microscopic and macroscopic homogeneity,
which is a necessity for any application. Different types of crystals being used are semiconductor crystals, oxide crys-
tals, alkali halide crystals, and nonlinear optical (NLO) crystals. The NLO effect in organic molecules originates from a
strong donor–acceptor intermolecular interaction, a delocalized π-electron system, and also the ability to crystallize in non-
centrosymmetric space groups. Substitution on either of the phenyl rings greatly influences non-centrosymmetric crystal
packing. It is speculated that in order to improve the activity, more bulky substituents should be introduced to increase
the spontaneous polarization of non-centrosymmetric crystals (Fichou et al., 1988). The molecular hyperpolarizability is
strongly influenced not only by the electronic effect but also by the steric effect of the substituent (Cho et al., 1996). Among
several organic compounds reported for NLO properties, chalcone derivatives are notable materials for their excellent blue
light transmittance and good crystallizability. They provide a necessary configuration to show an NLO property with two
planar rings connected through a conjugated double bond (Goto et al., 1991; Uchida et al., 1998; Tam et al., 1989; Indira
et al., 2002, Sarojini et al., 2006). The crystal structures of 1,5-bis(4-chlorophenyl)penta-1,4-dien-3-one (Butcher et al.,
2006), 5-phenyl-1-(2-thienyl)penta-2,4-dien-1-one (Yathirajan et al., 2007) and 1,5-bis(4-methoxyphenyl)penta-1,4-dien-
3-one (Harrison et al., 2006) have been reported. The paper reports crystal structure of the title compound. Fig. 1 shows
the molecular structure. The geometry is unexceptional.
Experimental
The title compound is synthesized according to the method reported in the literature (Furniss et al., 1989) with a yield of
75-80%. The compound is purified by recrystallization from ethanol. The crystal growth is done in acetone solvent by slow
evaporation technique (m.p.333-37 K). Analysis for C
18
H
16
O: Found (Calculated): C: 87.50 (87.06%); H: 6.31 (6.49%).
Refinement
H atoms were placed at calculated positions and refined as riding on the respective carrier atoms, with C—H = 0.93-0.96
Å and U
iso
(H) = 1.2 U
eq
(C) or 1.5 U
eq
(C) for methyl H atoms.
Figures
Fig. 1. : The molecular structure of (I). Displacement ellipsoids are drawn at the 50% probab-
ility level.
supplementary materials
sup-2
1-(4-Methylphenyl)-5-phenylpenta-2,4-dien-1-one
Crystal data
C
18
H
16
O
F
000
= 528
M
r
= 248.33
D
x
= 1.170 Mg m
−3
Monoclinic, P2
1
/c
Mo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ybc Cell parameters from 31 reflections
a = 7.7215 (12) Å
θ = 5.8–19.2º
b = 10.6985 (12) Å
µ = 0.07 mm
−1
c = 17.331 (3) Å T = 298 K
β = 99.550 (13)º Block, colourless
V = 1411.9 (4) Å
3
0.46 × 0.44 × 0.16 mm
Z = 4
Data collection
Bruker-Nonius KappaCCD diffractometer
R
int
= 0.083
Radiation source: fine-focus sealed tube
θ
max
= 25.0º
φ and ω scans
θ
min
= 4.5º
Absorption correction: none
h = −9→9
12654 measured reflections
k = −12→12
2465 independent reflections
l = −20→20
1411 reflections with I > 2σ(I)
Refinement
Refinement on F
2
H-atom parameters constrained
Least-squares matrix: full
w = 1/[σ
2
(F
o
2
) + (0.0454P)
2
+ 0.599P]
where P = (F
o
2
+ 2F
c
2
)/3
R[F
2
> 2σ(F
2
)] = 0.068
(Δ/σ)
max
< 0.001
wR(F
2
) = 0.162
Δρ
max
= 0.23 e Å
−3
S = 1.12
Δρ
min
= −0.14 e Å
−3
2465 reflections Extinction correction: none
172 parameters
Primary atom site location: structure-invariant direct
methods
Secondary atom site location: difference Fourier map
Special details
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The
cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds
in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used
for estimating esds involving l.s. planes.
supplementary materials
sup-3
Refinement. Refinement of F
2
against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F
2
, convention-
al R-factors R are based on F, with F set to zero for negative F
2
. The threshold expression of F
2
> 2sigma(F
2
) is used only for calculat-
ing R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F
2
are statistically about twice
as large as those based on F, and R- factors based on ALL data will be even larger.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å
2
)
x y z
U
iso
*/U
eq
C1 0.8540 (4) 0.4877 (3) 0.58254 (18) 0.0693 (9)
C2 0.9516 (5) 0.4357 (3) 0.6484 (2) 0.0797 (10)
C3 0.9547 (5) 0.4901 (4) 0.7199 (2) 0.0812 (10)
C4 0.8622 (5) 0.5971 (4) 0.72512 (19) 0.0854 (11)
C5 0.7655 (4) 0.6509 (3) 0.65946 (17) 0.0696 (9)
C6 0.7598 (4) 0.5958 (3) 0.58691 (15) 0.0555 (7)
C7 0.6567 (4) 0.6560 (3) 0.51811 (17) 0.0654 (8)
C8 0.6335 (4) 0.6166 (3) 0.44402 (16) 0.0639 (8)
C9 0.5317 (4) 0.6825 (3) 0.38073 (17) 0.0632 (8)
C10 0.5010 (4) 0.6488 (3) 0.30626 (16) 0.0605 (8)
C11 0.3920 (4) 0.7267 (3) 0.24737 (17) 0.0578 (8)
C12 0.3346 (4) 0.6776 (3) 0.16667 (15) 0.0510 (7)
C13 0.3969 (4) 0.5667 (3) 0.13931 (16) 0.0622 (8)
C14 0.3401 (4) 0.5283 (3) 0.06311 (17) 0.0674 (9)
C15 0.2203 (4) 0.5965 (3) 0.01268 (16) 0.0601 (8)
C16 0.1533 (4) 0.7044 (3) 0.04084 (18) 0.0681 (9)
C17 0.2110 (4) 0.7453 (3) 0.11586 (18) 0.0656 (8)
C18 0.1592 (5) 0.5536 (4) −0.07059 (17) 0.0819 (11)
O1 0.3463 (3) 0.8317 (2) 0.26439 (12) 0.0830 (7)
H1 0.8520 0.4490 0.5344 0.083*
H2 1.0158 0.3631 0.6442 0.096*
H3 1.0192 0.4543 0.7644 0.097*
H4 0.8640 0.6347 0.7736 0.102*
H5 0.7039 0.7246 0.6640 0.084*
H7 0.6010 0.7305 0.5272 0.078*
H8 0.6866 0.5420 0.4331 0.077*
H9 0.4814 0.7574 0.3931 0.076*
H10 0.5490 0.5747 0.2910 0.073*
H13 0.4771 0.5181 0.1723 0.075*
H14 0.3842 0.4544 0.0457 0.081*
H16 0.0678 0.7500 0.0085 0.082*
H17 0.1666 0.8194 0.1328 0.079*
H18A 0.2329 0.5901 −0.1042 0.123*
H18B 0.0396 0.5795 −0.0872 0.123*
H18C 0.1664 0.4641 −0.0731 0.123*
Atomic displacement parameters (Å
2
)
U
11
U
22
U
33
U
12
U
13
U
23
