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The title compound, C18H16O2, was prepared using literature procedures and crystallized from an acetone-toluene solution (50:50 v/v). The dihedral angle between the two aromatic rings is 9.28 (8) Å. The crystal packing is stabilized by van der Waals forces.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807033491/pr2008sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807033491/pr2008Isup2.hkl
Contains datablock I

CCDC reference: 657798

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.062
  • wR factor = 0.143
  • Data-to-parameter ratio = 14.5

checkCIF/PLATON results

No syntax errors found



Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.114 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.11
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

The title compound, (I), is a optically active molecule. The present-day demand is for large, high quality ferroelectric and 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. This paper reports crystal structure of the title compound. Fig 1 shows the molecular structure. The geometry of the molecule is unexceptional. The dihedral angle between the two phenyl groups is 9.28 (9)\%. The crystal packing is stabilized by van der Waals forces.

Related literature top

For related literature, see: Butcher et al. (2006); Cho et al. (1996); Fichou et al. (1988); Furniss et al. (1989); Goto et al. (1991); Harrison et al. (2006); Indira et al. (2002); Sarojini et al. (2006); Tam et al. (1989); Uchida et al. (1998); Yathirajan et al. (2007).

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 was purified by recrystallization from ethanol. The crystal grew by slow evaporation from an acetone:toluene solution (50:50). Analysis for C18H16O2: Found (Calculated): C: 81.50 (81.79); H: 6.01(6.10).

Refinement top

H atoms were placed at calculated positions and refined using a riding model on the respective carrier atoms.

Structure description top

The title compound, (I), is a optically active molecule. The present-day demand is for large, high quality ferroelectric and 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. This paper reports crystal structure of the title compound. Fig 1 shows the molecular structure. The geometry of the molecule is unexceptional. The dihedral angle between the two phenyl groups is 9.28 (9)\%. The crystal packing is stabilized by van der Waals forces.

For related literature, see: Butcher et al. (2006); Cho et al. (1996); Fichou et al. (1988); Furniss et al. (1989); Goto et al. (1991); Harrison et al. (2006); Indira et al. (2002); Sarojini et al. (2006); Tam et al. (1989); Uchida et al. (1998); Yathirajan et al. (2007).

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). Thermal ellipsoids at the 50% probability level.
1-(4-Methoxyphenyl)-5-phenylpenta-2,4-dien-1-one top
Crystal data top
C18H16O2F(000) = 560
Mr = 264.32Dx = 1.229 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 23 reflections
a = 29.017 (7) Åθ = 7.9–16.8°
b = 5.8088 (14) ŵ = 0.08 mm1
c = 8.4868 (10) ÅT = 298 K
β = 93.308 (16)°Block, colourless
V = 1428.1 (5) Å30.35 × 0.30 × 0.28 mm
Z = 4
Data collection top
Nonius KappaCCD area-detector
diffractometer
Rint = 0.114
Radiation source: fine-focus sealed tubeθmax = 25.5°, θmin = 4.5°
ω scansh = 3535
13388 measured reflectionsk = 66
2633 independent reflectionsl = 1010
1558 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)] = 0.062H-atom parameters constrained
wR(F2) = 0.143 w = 1/[σ2(Fo2) + (0.0295P)2 + 0.4375P]
where P = (Fo2 + 2Fc2)/3
S = 1.12(Δ/σ)max < 0.001
2633 reflectionsΔρmax = 0.11 e Å3
181 parametersΔρmin = 0.15 e Å3
0 restraints
Crystal data top
C18H16O2V = 1428.1 (5) Å3
Mr = 264.32Z = 4
Monoclinic, P21/cMo Kα radiation
a = 29.017 (7) ŵ = 0.08 mm1
b = 5.8088 (14) ÅT = 298 K
c = 8.4868 (10) Å0.35 × 0.30 × 0.28 mm
β = 93.308 (16)°
Data collection top
Nonius KappaCCD area-detector
diffractometer
1558 reflections with I > 2σ(I)
13388 measured reflectionsRint = 0.114
2633 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0620 restraints
wR(F2) = 0.143H-atom parameters constrained
S = 1.12Δρmax = 0.11 e Å3
2633 reflectionsΔρmin = 0.15 e Å3
181 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
C10.38172 (9)0.0845 (4)0.2302 (3)0.0578 (6)
C20.36674 (9)0.1304 (4)0.2890 (3)0.0646 (7)
C30.39574 (11)0.2695 (5)0.3692 (3)0.0749 (8)
C40.43995 (12)0.2026 (5)0.3913 (3)0.0838 (9)
C50.45590 (10)0.0061 (5)0.3321 (3)0.0819 (8)
C60.42687 (10)0.1465 (5)0.2519 (3)0.0712 (7)
C70.35161 (9)0.2417 (4)0.1507 (3)0.0647 (7)
C80.31018 (9)0.2028 (4)0.0991 (3)0.0642 (7)
C90.28328 (9)0.3786 (4)0.0280 (3)0.0674 (7)
C100.24440 (9)0.3508 (4)0.0427 (3)0.0684 (7)
C110.22146 (9)0.5437 (4)0.1185 (3)0.0634 (7)
C120.17642 (8)0.5074 (4)0.1882 (3)0.0570 (6)
C130.15943 (9)0.6766 (4)0.2867 (3)0.0664 (7)
C140.11768 (9)0.6524 (4)0.3513 (3)0.0688 (7)
C150.09115 (9)0.4579 (4)0.3199 (3)0.0631 (7)
C160.10710 (9)0.2878 (4)0.2227 (3)0.0697 (7)
C170.14966 (9)0.3132 (4)0.1591 (3)0.0677 (7)
C180.02246 (11)0.2487 (6)0.3656 (4)0.0971 (10)
O10.23951 (7)0.7363 (3)0.1259 (3)0.0929 (7)
O20.04997 (6)0.4496 (3)0.3901 (2)0.0784 (6)
H20.33690.17940.27360.078*
H30.38520.41080.40890.090*
H40.45920.29770.44620.101*
H50.48600.05180.34610.098*
H60.43790.28650.21140.085*
H70.36300.39020.13370.078*
H80.29790.05480.10940.077*
H90.29450.52880.03220.081*
H100.23110.20460.04450.082*
H130.17680.80860.30880.080*
H140.10710.76740.41680.083*
H160.08940.15700.20010.084*
H170.16050.19670.09540.081*
H18A0.01560.22760.25470.146*
H18B0.00570.26640.41840.146*
H18C0.03890.11630.40730.146*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0763 (17)0.0467 (15)0.0503 (13)0.0012 (13)0.0038 (12)0.0023 (12)
C20.0840 (18)0.0550 (16)0.0548 (14)0.0046 (14)0.0018 (13)0.0003 (13)
C30.111 (2)0.0544 (17)0.0593 (16)0.0032 (17)0.0069 (16)0.0036 (13)
C40.108 (3)0.072 (2)0.0723 (19)0.0150 (18)0.0178 (17)0.0006 (16)
C50.080 (2)0.076 (2)0.090 (2)0.0022 (17)0.0174 (16)0.0018 (18)
C60.083 (2)0.0578 (17)0.0732 (17)0.0076 (15)0.0098 (15)0.0011 (14)
C70.0801 (19)0.0522 (15)0.0618 (15)0.0038 (14)0.0041 (14)0.0027 (13)
C80.0757 (19)0.0502 (15)0.0662 (16)0.0014 (14)0.0015 (14)0.0042 (12)
C90.0787 (19)0.0543 (16)0.0687 (16)0.0011 (14)0.0009 (14)0.0021 (14)
C100.0698 (18)0.0538 (16)0.0814 (18)0.0005 (13)0.0013 (15)0.0091 (14)
C110.0692 (17)0.0502 (16)0.0696 (16)0.0000 (13)0.0063 (13)0.0030 (13)
C120.0656 (16)0.0454 (14)0.0589 (14)0.0050 (12)0.0059 (12)0.0014 (12)
C130.0731 (19)0.0469 (15)0.0782 (17)0.0020 (13)0.0045 (15)0.0080 (13)
C140.0793 (19)0.0512 (16)0.0753 (17)0.0108 (14)0.0008 (15)0.0112 (13)
C150.0666 (17)0.0588 (16)0.0634 (15)0.0092 (14)0.0017 (13)0.0016 (14)
C160.0761 (19)0.0540 (16)0.0786 (18)0.0076 (14)0.0002 (15)0.0122 (14)
C170.0776 (19)0.0542 (16)0.0711 (17)0.0006 (14)0.0037 (14)0.0126 (13)
C180.083 (2)0.092 (2)0.118 (3)0.0125 (19)0.0188 (19)0.008 (2)
O10.0942 (15)0.0578 (12)0.1283 (18)0.0129 (11)0.0214 (12)0.0151 (12)
O20.0736 (12)0.0743 (13)0.0878 (13)0.0044 (10)0.0081 (10)0.0039 (10)
Geometric parameters (Å, º) top
C1—C61.385 (3)C16—C171.387 (3)
C1—C21.401 (3)C18—O21.420 (3)
C1—C71.455 (3)C2—H20.9300
C2—C31.374 (3)C3—H30.9300
C3—C41.367 (4)C4—H40.9300
C4—C51.379 (4)C5—H50.9300
C5—C61.379 (4)C6—H60.9300
C7—C81.325 (3)C7—H70.9300
C8—C91.437 (3)C8—H80.9300
C9—C101.320 (3)C9—H90.9300
C10—C111.467 (3)C10—H100.9300
C11—O11.232 (3)C13—H130.9300
C11—C121.483 (3)C14—H140.9300
C12—C171.382 (3)C16—H160.9300
C12—C131.395 (3)C17—H170.9300
C13—C141.368 (3)C18—H18A0.9600
C14—C151.383 (3)C18—H18B0.9600
C15—O21.369 (3)C18—H18C0.9600
C15—C161.384 (3)
C6—C1—C2117.5 (2)C2—C3—H3119.6
C6—C1—C7120.0 (2)C3—C4—H4120.0
C2—C1—C7122.7 (2)C5—C4—H4120.0
C3—C2—C1120.6 (3)C6—C5—H5120.2
C4—C3—C2120.7 (3)C4—C5—H5120.2
C3—C4—C5119.9 (3)C5—C6—H6119.2
C6—C5—C4119.5 (3)C1—C6—H6119.2
C5—C6—C1121.7 (3)C8—C7—H7115.5
C8—C7—C1129.1 (2)C1—C7—H7115.5
C7—C8—C9123.1 (2)C7—C8—H8118.5
C10—C9—C8127.3 (2)C9—C8—H8118.5
C9—C10—C11121.9 (2)C10—C9—H9116.4
O1—C11—C10120.5 (2)C8—C9—H9116.4
O1—C11—C12119.5 (2)C9—C10—H10119.0
C10—C11—C12120.1 (2)C11—C10—H10119.0
C17—C12—C13117.8 (2)C14—C13—H13119.3
C17—C12—C11123.1 (2)C12—C13—H13119.3
C13—C12—C11119.3 (2)C13—C14—H14119.8
C14—C13—C12121.4 (2)C15—C14—H14119.8
C13—C14—C15120.3 (2)C15—C16—H16120.2
O2—C15—C16124.5 (2)C17—C16—H16120.2
O2—C15—C14115.9 (2)C12—C17—H17119.2
C16—C15—C14119.5 (2)C16—C17—H17119.2
C15—C16—C17119.6 (2)O2—C18—H18A109.5
C12—C17—C16121.6 (2)O2—C18—H18B109.5
C15—O2—C18117.7 (2)H18A—C18—H18B109.5
C3—C2—H2119.7O2—C18—H18C109.5
C1—C2—H2119.7H18A—C18—H18C109.5
C4—C3—H3119.6H18B—C18—H18C109.5

Experimental details

Crystal data
Chemical formulaC18H16O2
Mr264.32
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)29.017 (7), 5.8088 (14), 8.4868 (10)
β (°) 93.308 (16)
V3)1428.1 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.35 × 0.30 × 0.28
Data collection
DiffractometerNonius KappaCCD area-detector
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
13388, 2633, 1558
Rint0.114
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.062, 0.143, 1.12
No. of reflections2633
No. of parameters181
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.11, 0.15

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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