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The title compound, C18H16O, features two conjugate double bonds, both in E conformations. The molecule is essentially planar: the dihedral angle between the two phenyl groups is 9.4 (1)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807020582/rz2134sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807020582/rz2134Isup2.hkl
Contains datablock I

CCDC reference: 651396

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C)= 0.004 Å
  • R factor = 0.068
  • wR factor = 0.162
  • Data-to-parameter ratio = 14.3

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Comment top

The title compound, (I), C18H16O, 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 inhomogenities. 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 crystals, 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 noncentrosymmetric 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.

Related literature top

For related structures, see: Butcher et al. (2006), Yathirajan et al. (2007), Harrison et al. (2006). For non-linear optical crystals, 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 top

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 C18H16O: Found (Calculated): C: 87.50 (87.06%); H: 6.31 (6.49%).

Refinement top

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 Uiso(H) = 1.2 Ueq(C) or 1.5 Ueq(C) for methyl H atoms.

Structure description top

The title compound, (I), C18H16O, 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 inhomogenities. 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 crystals, 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 noncentrosymmetric 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.

For related structures, see: Butcher et al. (2006), Yathirajan et al. (2007), Harrison et al. (2006). For non-linear optical crystals, 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).

Computing details top

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 publication: publCIF (Westrip, 2007).

Figures top
[Figure 1] Fig. 1. : The molecular structure of (I). Displacement ellipsoids are drawn at the 50% probability level.
1-(4-Methylphenyl)-5-phenylpenta-2,4-dien-1-one top
Crystal data top
C18H16OF(000) = 528
Mr = 248.33Dx = 1.170 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 31 reflections
a = 7.7215 (12) Åθ = 5.8–19.2°
b = 10.6985 (12) ŵ = 0.07 mm1
c = 17.331 (3) ÅT = 298 K
β = 99.550 (13)°Block, colourless
V = 1411.9 (4) Å30.46 × 0.44 × 0.16 mm
Z = 4
Data collection top
Bruker-Nonius KappaCCD
diffractometer
Rint = 0.083
Radiation source: fine-focus sealed tubeθmax = 25.0°, θmin = 4.5°
φ and ω scansh = 99
12654 measured reflectionsk = 1212
2465 independent reflectionsl = 2020
1411 reflections with I > 2σ(I)
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.068H-atom parameters constrained
wR(F2) = 0.162 w = 1/[σ2(Fo2) + (0.0454P)2 + 0.599P]
where P = (Fo2 + 2Fc2)/3
S = 1.12(Δ/σ)max < 0.001
2465 reflectionsΔρmax = 0.23 e Å3
172 parametersΔρmin = 0.14 e Å3
0 restraints
Crystal data top
C18H16OV = 1411.9 (4) Å3
Mr = 248.33Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.7215 (12) ŵ = 0.07 mm1
b = 10.6985 (12) ÅT = 298 K
c = 17.331 (3) Å0.46 × 0.44 × 0.16 mm
β = 99.550 (13)°
Data collection top
Bruker-Nonius KappaCCD
diffractometer
1411 reflections with I > 2σ(I)
12654 measured reflectionsRint = 0.083
2465 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0680 restraints
wR(F2) = 0.162H-atom parameters constrained
S = 1.12Δρmax = 0.23 e Å3
2465 reflectionsΔρmin = 0.14 e Å3
172 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 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 (Å2) top
xyzUiso*/Ueq
C10.8540 (4)0.4877 (3)0.58254 (18)0.0693 (9)
C20.9516 (5)0.4357 (3)0.6484 (2)0.0797 (10)
C30.9547 (5)0.4901 (4)0.7199 (2)0.0812 (10)
C40.8622 (5)0.5971 (4)0.72512 (19)0.0854 (11)
C50.7655 (4)0.6509 (3)0.65946 (17)0.0696 (9)
C60.7598 (4)0.5958 (3)0.58691 (15)0.0555 (7)
C70.6567 (4)0.6560 (3)0.51811 (17)0.0654 (8)
C80.6335 (4)0.6166 (3)0.44402 (16)0.0639 (8)
C90.5317 (4)0.6825 (3)0.38073 (17)0.0632 (8)
C100.5010 (4)0.6488 (3)0.30626 (16)0.0605 (8)
C110.3920 (4)0.7267 (3)0.24737 (17)0.0578 (8)
C120.3346 (4)0.6776 (3)0.16667 (15)0.0510 (7)
C130.3969 (4)0.5667 (3)0.13931 (16)0.0622 (8)
C140.3401 (4)0.5283 (3)0.06311 (17)0.0674 (9)
C150.2203 (4)0.5965 (3)0.01268 (16)0.0601 (8)
C160.1533 (4)0.7044 (3)0.04084 (18)0.0681 (9)
C170.2110 (4)0.7453 (3)0.11586 (18)0.0656 (8)
C180.1592 (5)0.5536 (4)0.07059 (17)0.0819 (11)
O10.3463 (3)0.8317 (2)0.26439 (12)0.0830 (7)
H10.85200.44900.53440.083*
H21.01580.36310.64420.096*
H31.01920.45430.76440.097*
H40.86400.63470.77360.102*
H50.70390.72460.66400.084*
H70.60100.73050.52720.078*
H80.68660.54200.43310.077*
H90.48140.75740.39310.076*
H100.54900.57470.29100.073*
H130.47710.51810.17230.075*
H140.38420.45440.04570.081*
H160.06780.75000.00850.082*
H170.16660.81940.13280.079*
H18A0.23290.59010.10420.123*
H18B0.03960.57950.08720.123*
H18C0.16640.46410.07310.123*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.084 (2)0.069 (2)0.0520 (19)0.0019 (18)0.0018 (16)0.0047 (16)
C20.091 (3)0.072 (2)0.074 (2)0.0115 (19)0.0060 (19)0.0054 (19)
C30.081 (2)0.100 (3)0.057 (2)0.000 (2)0.0065 (17)0.014 (2)
C40.094 (3)0.113 (3)0.046 (2)0.001 (2)0.0017 (18)0.005 (2)
C50.070 (2)0.087 (2)0.0516 (19)0.0044 (18)0.0093 (15)0.0084 (17)
C60.0551 (17)0.0655 (19)0.0453 (17)0.0020 (15)0.0061 (13)0.0011 (15)
C70.070 (2)0.070 (2)0.0549 (19)0.0020 (17)0.0052 (15)0.0034 (16)
C80.068 (2)0.068 (2)0.0533 (19)0.0007 (16)0.0040 (15)0.0024 (16)
C90.0635 (19)0.068 (2)0.0554 (19)0.0002 (15)0.0019 (15)0.0007 (16)
C100.0664 (19)0.065 (2)0.0477 (17)0.0007 (16)0.0025 (14)0.0029 (15)
C110.0599 (18)0.061 (2)0.0532 (19)0.0036 (15)0.0103 (14)0.0016 (15)
C120.0543 (17)0.0542 (17)0.0452 (16)0.0035 (14)0.0101 (13)0.0066 (13)
C130.0660 (19)0.073 (2)0.0466 (17)0.0136 (16)0.0053 (14)0.0071 (15)
C140.082 (2)0.068 (2)0.0519 (19)0.0115 (17)0.0086 (16)0.0052 (16)
C150.0641 (19)0.070 (2)0.0457 (17)0.0134 (16)0.0091 (14)0.0078 (16)
C160.076 (2)0.068 (2)0.055 (2)0.0005 (17)0.0041 (16)0.0149 (16)
C170.075 (2)0.0575 (19)0.062 (2)0.0062 (16)0.0050 (17)0.0089 (15)
C180.087 (2)0.104 (3)0.0521 (19)0.018 (2)0.0022 (17)0.0051 (18)
O10.1052 (19)0.0669 (15)0.0716 (15)0.0141 (13)0.0017 (13)0.0121 (12)
Geometric parameters (Å, º) top
C1—C61.373 (4)C15—C181.516 (4)
C1—C21.379 (4)C16—C171.377 (4)
C2—C31.367 (4)C1—H10.9300
C3—C41.358 (5)C2—H20.9300
C4—C51.381 (4)C3—H30.9300
C5—C61.384 (4)C4—H40.9300
C6—C71.471 (4)C5—H50.9300
C7—C81.337 (4)C7—H70.9300
C8—C91.427 (4)C8—H80.9300
C9—C101.325 (4)C9—H90.9300
C10—C111.471 (4)C10—H100.9300
C11—O11.227 (3)C13—H130.9300
C11—C121.494 (4)C14—H140.9300
C12—C171.391 (4)C16—H160.9300
C12—C131.391 (4)C17—H170.9300
C13—C141.386 (4)C18—H18A0.9600
C14—C151.373 (4)C18—H18B0.9600
C15—C161.385 (4)C18—H18C0.9600
C6—C1—C2121.0 (3)C4—C3—H3120.4
C3—C2—C1120.5 (3)C2—C3—H3120.4
C4—C3—C2119.1 (3)C3—C4—H4119.5
C3—C4—C5120.9 (3)C5—C4—H4119.5
C4—C5—C6120.4 (3)C4—C5—H5119.8
C1—C6—C5118.0 (3)C6—C5—H5119.8
C1—C6—C7123.0 (3)C8—C7—H7116.1
C5—C6—C7119.0 (3)C6—C7—H7116.1
C8—C7—C6127.8 (3)C7—C8—H8118.1
C7—C8—C9123.7 (3)C9—C8—H8118.1
C10—C9—C8127.2 (3)C10—C9—H9116.4
C9—C10—C11121.0 (3)C8—C9—H9116.4
O1—C11—C10120.3 (3)C9—C10—H10119.5
O1—C11—C12119.6 (3)C11—C10—H10119.5
C10—C11—C12120.1 (3)C14—C13—H13119.8
C17—C12—C13117.8 (3)C12—C13—H13119.8
C17—C12—C11118.6 (3)C15—C14—H14119.1
C13—C12—C11123.6 (3)C13—C14—H14119.1
C14—C13—C12120.4 (3)C17—C16—H16119.4
C15—C14—C13121.7 (3)C15—C16—H16119.4
C14—C15—C16117.9 (3)C16—C17—H17119.4
C14—C15—C18121.3 (3)C12—C17—H17119.4
C16—C15—C18120.8 (3)C15—C18—H18A109.5
C17—C16—C15121.1 (3)C15—C18—H18B109.5
C16—C17—C12121.1 (3)H18A—C18—H18B109.5
C6—C1—H1119.5C15—C18—H18C109.5
C2—C1—H1119.5H18A—C18—H18C109.5
C3—C2—H2119.7H18B—C18—H18C109.5
C1—C2—H2119.7

Experimental details

Crystal data
Chemical formulaC18H16O
Mr248.33
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)7.7215 (12), 10.6985 (12), 17.331 (3)
β (°) 99.550 (13)
V3)1411.9 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.46 × 0.44 × 0.16
Data collection
DiffractometerBruker-Nonius KappaCCD
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
12654, 2465, 1411
Rint0.083
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.068, 0.162, 1.12
No. of reflections2465
No. of parameters172
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.23, 0.14

Computer programs: COLLECT (Nonius, 1999), DIRAX/LSQ (Duisenberg, 1992), EVALCCD (Duisenberg et al., 2003), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2007).

 

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