supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportcited insimilar papers buy article online

Acta Cryst. (2007). E63, o2928    [ doi:10.1107/S1600536807024038 ]

1-(4-Hydroxyphenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one

W. T. A. Harrison, V. Kumari, H. J. Ravindra and S. M. Dharmaprakash

Abstract top

In the chalcone-derived title compound, C18H18O5, the dihedral angle between the aromatic ring mean planes is 16.64 (15)°. In the crystal structure, adjacent molecules interact by way of O-H...O=C hydrogen bonds, leading to C(8) chains. A C-H...[pi] interaction also helps to stabilize the centrosymmetric crystal packing.

Comment top

Organic nonlinear optical materials derived from chalcone are attractive due to their large second harmonic conversion efficiency and excellent blue light transmission (Harrison et al.,. 2006; Butcher et al.,. 2006; Zhao et al.,. 2000). These chalcones crystallize in a non-centrosymmetric crystal structure and provide a necessary configuration for NLO activity with two aromatic rings connected through a conjugated chian (Uchida et al., 1998; Indira et al., 2002.). The chalcone molecules also show good third order nonlinear response (Kiran et al. 2007). The nonlinear refractive index of the title compound was measured to be of the order 10-11 esu. With this background and also to better understand the structure—nonlinear optical property relationship for this family of compounds, the single-crystal X-ray diffraction study of the title compound, (I) has been carried out.

The molecular structure of (I) is shown in Fig. 1. The bond lengths and angles for (I) are comparable with related molecules such as 1-(4-chlorophenyl) -3-(2,4,5-trimethoxyphenyl)-prop-2-en-1-one (Patil et al.,. 2006), and 1-phenyl-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (Teh et al.,. 2006). The C12 and C14 methoxy groups are coplanar with the attached C10—C15 benzene ring with C11—C12—O3—C16 and C15—C14—O5—C18 torsion angles of -3.3 (4)° and 2.1 (4)°, respectively. The other (C13) methoxy group is twisted away form the C10—C15 ring, with a C12—C13—O4—C17 torsion angle of -79.7 (3)°. This correlates with the devations of C16, C17 and C18 from the mean plane of the C10—C15 ring by 0.074 (6), 1.225 (6) and -0.013 (6) Å, respectively.

The dihedral angle between two benzene rings C10—C15 and C1—C6 is 16.64 (13)°. The mean plane through the enone fragment (O2/C7—C9) makes dihedral angles of 10.29 (13)° and 6.35 (14)° with C1—C6 and C10—C15 benzene ring planes, respectively.

The hydrogen bond parameters are listed in Table 1. The crystal structure is stabilized by an O—H···O hydrogen bond, leading to a C6 chain along the c-axis (Fig. 2). A weak C—H···π interaction also occurs (Fig. 3).

Related literature top

For related chalcone derivatives with different substituents at the 4-hydroxy position, see: Teh et al., 2006; Ng, Patil et al., 2006; Ng, Razak, Fun, Patil, Dharmaprakash & Shettigar, 2006; Ng, Razak, Fun, Patil & Dharmaprakash, 2006. For the 2-hydroxy isomer of the title compound, which coincidentally possesses a very similar unit cell, see Wu et al. (2005).

For other relevant literature see: Butcher et al. (2006); Harrison et al. (2006); Indira et al. (2002); Kiran et al. (2007); Patil et al. (2006); Uchida et al. (1998); Vogel (1999); Zhao et al. (2000).

Experimental top

The title compound was synthesized according to a literature method (Vogel, 1999). The compound was purified by successive recrystallization from DMF solvent. The single-crystal of (I) required for X-ray diffraction analysis was obtained by slow evaporation of a DMF solution.

Refinement top

The O-bound H atom was located in a differnce map and refined as riding in its as-found relative position with Uiso(H) = 1.2Ueq(O). All the C-bound hydrogen atoms were placed in calculated positions (C—H = 0.95–0.99 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C). The methyl groups were allowed to rotate but not to tip to best fit the electron density.

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top
[Figure 1] Fig. 1. View of the molecular structure of (I) showing 50% displacement ellipsoids (H atoms are drawn as spheres of arbitrary radius).
[Figure 2] Fig. 2. Part of a C(8) chain in (I) with hydrogen bonds shown as dashed lines. All hydrogen atoms except H1 omitted for clarity. Symmetry code as in Table 1.
[Figure 3] Fig. 3. The packing for (I) showing the C—H···π interaction as a dashed line.
1-(4-hydroxyphenyl)-3-(3,4,5-trimethoxyphenyl)-2-propen-1-one top
Crystal data top
C18H18O5F(000) = 664
Mr = 314.32Dx = 1.322 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 853 reflections
a = 12.4431 (18) Åθ = 4.7–25.1°
b = 8.5528 (12) ŵ = 0.10 mm−1
c = 15.470 (2) ÅT = 295 K
β = 106.399 (2)°Block, pale yellow
V = 1579.4 (4) Å30.25 × 0.20 × 0.20 mm
Z = 4
Data collection top
Bruker SMART1000 CCD
diffractometer		3088 independent reflections
Radiation source: fine-focus sealed tube1656 reflections with I > 2σ(I)
graphiteRint = 0.057
ω scansθmax = 26.0°, θmin = 4.7°
Absorption correction: multi-scan
(SADABS; Bruker, 1999)		h = −15→8
Tmin = 0.960, Tmax = 0.981k = −7→10
7097 measured reflectionsl = −18→19
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)] = 0.066Hydrogen site location: difmap and geom
wR(F2) = 0.179H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0929P)2]
where P = (Fo2 + 2Fc2)/3
3088 reflections(Δ/σ)max < 0.001
211 parametersΔρmax = 0.33 e Å−3
0 restraintsΔρmin = −0.20 e Å−3
Crystal data top
C18H18O5V = 1579.4 (4) Å3
Mr = 314.32Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.4431 (18) ŵ = 0.10 mm−1
b = 8.5528 (12) ÅT = 295 K
c = 15.470 (2) Å0.25 × 0.20 × 0.20 mm
β = 106.399 (2)°
Data collection top
Bruker SMART1000 CCD
diffractometer		3088 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1999)		1656 reflections with I > 2σ(I)
Tmin = 0.960, Tmax = 0.981Rint = 0.057
7097 measured reflectionsθmax = 26.0°
Refinement top
R[F2 > 2σ(F2)] = 0.066H-atom parameters constrained
wR(F2) = 0.179Δρmax = 0.33 e Å−3
S = 1.00Δρmin = −0.20 e Å−3
3088 reflectionsAbsolute structure: ?
211 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
C10.3208 (2)0.4896 (3)0.30271 (17)0.0493 (7)
H1A0.27540.42030.32280.059*
C20.3227 (2)0.4838 (3)0.21394 (17)0.0522 (7)
H20.27880.41120.17470.063*
C30.3899 (2)0.5859 (3)0.18339 (16)0.0480 (7)
C40.4558 (2)0.6933 (4)0.24210 (18)0.0518 (7)
H40.50140.76180.22180.062*
C50.4535 (2)0.6982 (3)0.33056 (17)0.0495 (7)
H50.49820.77030.36960.059*
C60.3858 (2)0.5978 (3)0.36287 (16)0.0436 (7)
C70.3856 (2)0.6078 (3)0.45843 (17)0.0485 (7)
C80.3021 (3)0.5194 (4)0.48890 (18)0.0557 (8)
H80.24500.46850.44620.067*
C90.3050 (2)0.5093 (4)0.57539 (18)0.0519 (7)
H90.36430.56030.61580.062*
C100.2269 (2)0.4285 (3)0.61475 (17)0.0483 (7)
C110.1338 (2)0.3478 (4)0.56173 (18)0.0540 (8)
H110.12090.34290.49960.065*
C120.0609 (2)0.2754 (4)0.60208 (19)0.0536 (8)
C130.0808 (2)0.2791 (3)0.69571 (18)0.0511 (7)
C140.1739 (2)0.3589 (3)0.74823 (16)0.0487 (7)
C150.2463 (2)0.4328 (3)0.70822 (17)0.0491 (7)
H150.30840.48570.74380.059*
C16−0.0614 (3)0.1908 (4)0.4622 (2)0.0831 (11)
H16A−0.13100.13630.43860.125*
H16B−0.00340.13800.44390.125*
H16C−0.06870.29590.43950.125*
C17−0.0895 (3)0.2857 (5)0.7318 (2)0.0783 (10)
H17A−0.13240.22940.76430.118*
H17B−0.13260.29650.67000.118*
H17C−0.07130.38750.75810.118*
C180.2756 (3)0.4307 (5)0.89628 (19)0.0819 (12)
H18A0.27310.41760.95730.123*
H18B0.27130.54000.88150.123*
H18C0.34440.38840.89000.123*
O10.3881 (2)0.5740 (3)0.09582 (12)0.0697 (7)
H10.43680.63550.07420.084*
O20.45533 (17)0.6910 (3)0.51111 (12)0.0603 (6)
O3−0.03409 (19)0.1939 (3)0.55607 (14)0.0720 (7)
O40.01136 (18)0.2021 (3)0.73646 (13)0.0642 (6)
O50.18695 (18)0.3539 (3)0.83935 (12)0.0628 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0551 (17)0.0436 (18)0.0499 (15)−0.0043 (14)0.0161 (13)0.0026 (12)
C20.0619 (18)0.0421 (18)0.0490 (15)−0.0073 (15)0.0097 (14)−0.0030 (12)
C30.0564 (17)0.0438 (17)0.0420 (14)0.0032 (14)0.0110 (13)0.0038 (12)
C40.0531 (16)0.0484 (19)0.0519 (16)−0.0040 (14)0.0119 (13)0.0067 (13)
C50.0512 (16)0.0461 (18)0.0467 (14)−0.0048 (14)0.0062 (12)−0.0021 (12)
C60.0442 (14)0.0411 (17)0.0437 (13)0.0049 (13)0.0098 (12)0.0024 (12)
C70.0501 (16)0.0484 (18)0.0469 (14)0.0090 (14)0.0135 (13)−0.0009 (13)
C80.0549 (17)0.061 (2)0.0496 (16)−0.0004 (16)0.0114 (14)−0.0013 (14)
C90.0556 (17)0.0503 (18)0.0491 (15)0.0059 (15)0.0137 (14)−0.0006 (13)
C100.0548 (16)0.0439 (18)0.0465 (15)0.0090 (14)0.0146 (13)0.0032 (12)
C110.0608 (17)0.057 (2)0.0417 (14)0.0041 (16)0.0107 (13)0.0013 (13)
C120.0546 (17)0.0496 (19)0.0520 (15)0.0019 (15)0.0077 (13)−0.0012 (13)
C130.0540 (16)0.0469 (18)0.0530 (16)0.0065 (15)0.0163 (14)0.0063 (13)
C140.0571 (16)0.0474 (18)0.0405 (14)0.0129 (15)0.0120 (13)0.0030 (12)
C150.0514 (16)0.0450 (18)0.0489 (15)0.0022 (14)0.0107 (13)−0.0021 (12)
C160.079 (2)0.079 (3)0.072 (2)−0.008 (2)−0.0092 (18)−0.0128 (18)
C170.064 (2)0.095 (3)0.084 (2)0.000 (2)0.0335 (18)0.008 (2)
C180.117 (3)0.085 (3)0.0390 (16)−0.009 (2)0.0151 (18)−0.0043 (16)
O10.0941 (17)0.0699 (16)0.0458 (11)−0.0159 (13)0.0208 (11)0.0009 (9)
O20.0637 (13)0.0664 (15)0.0508 (11)−0.0055 (11)0.0159 (10)−0.0122 (10)
O30.0737 (14)0.0739 (17)0.0663 (13)−0.0146 (13)0.0162 (11)−0.0057 (11)
O40.0677 (13)0.0592 (15)0.0684 (13)−0.0011 (12)0.0236 (11)0.0114 (10)
O50.0721 (14)0.0710 (15)0.0460 (10)0.0003 (12)0.0179 (10)0.0016 (10)
Geometric parameters (Å, °) top
C1—C21.381 (4)C11—H110.9300
C1—C61.397 (4)C12—O31.384 (3)
C1—H1A0.9300C12—C131.399 (4)
C2—C31.381 (4)C13—O41.373 (3)
C2—H20.9300C13—C141.392 (4)
C3—O11.352 (3)C14—O51.373 (3)
C3—C41.386 (4)C14—C151.382 (4)
C4—C51.377 (4)C15—H150.9300
C4—H40.9300C16—O31.395 (4)
C5—C61.391 (4)C16—H16A0.9600
C5—H50.9300C16—H16B0.9600
C6—C71.481 (4)C16—H16C0.9600
C7—O21.235 (3)C17—O41.429 (4)
C7—C81.466 (4)C17—H17A0.9600
C8—C91.331 (4)C17—H17B0.9600
C8—H80.9300C17—H17C0.9600
C9—C101.458 (4)C18—O51.369 (4)
C9—H90.9300C18—H18A0.9600
C10—C151.398 (3)C18—H18B0.9600
C10—C111.398 (4)C18—H18C0.9600
C11—C121.384 (4)O1—H10.9331
C2—C1—C6121.1 (3)O3—C12—C13114.8 (3)
C2—C1—H1A119.5C11—C12—C13120.6 (3)
C6—C1—H1A119.5O4—C13—C14119.7 (2)
C3—C2—C1120.0 (3)O4—C13—C12120.9 (3)
C3—C2—H2120.0C14—C13—C12119.4 (3)
C1—C2—H2120.0O5—C14—C15124.8 (3)
O1—C3—C2117.0 (3)O5—C14—C13114.9 (3)
O1—C3—C4123.1 (3)C15—C14—C13120.2 (2)
C2—C3—C4119.9 (2)C14—C15—C10120.5 (3)
C5—C4—C3119.8 (3)C14—C15—H15119.7
C5—C4—H4120.1C10—C15—H15119.7
C3—C4—H4120.1O3—C16—H16A109.5
C4—C5—C6121.5 (3)O3—C16—H16B109.5
C4—C5—H5119.3H16A—C16—H16B109.5
C6—C5—H5119.3O3—C16—H16C109.5
C5—C6—C1117.7 (2)H16A—C16—H16C109.5
C5—C6—C7119.6 (2)H16B—C16—H16C109.5
C1—C6—C7122.6 (3)O4—C17—H17A109.5
O2—C7—C8121.0 (2)O4—C17—H17B109.5
O2—C7—C6119.6 (3)H17A—C17—H17B109.5
C8—C7—C6119.5 (3)O4—C17—H17C109.5
C9—C8—C7122.4 (3)H17A—C17—H17C109.5
C9—C8—H8118.8H17B—C17—H17C109.5
C7—C8—H8118.8O5—C18—H18A109.5
C8—C9—C10128.2 (3)O5—C18—H18B109.5
C8—C9—H9115.9H18A—C18—H18B109.5
C10—C9—H9115.9O5—C18—H18C109.5
C15—C10—C11119.5 (3)H18A—C18—H18C109.5
C15—C10—C9118.6 (3)H18B—C18—H18C109.5
C11—C10—C9121.9 (2)C3—O1—H1119.2
C12—C11—C10119.8 (2)C12—O3—C16117.8 (3)
C12—C11—H11120.1C13—O4—C17113.3 (2)
C10—C11—H11120.1C18—O5—C14119.1 (2)
O3—C12—C11124.5 (3)
C6—C1—C2—C30.1 (4)C10—C11—C12—O3179.4 (3)
C1—C2—C3—O1179.9 (3)C10—C11—C12—C13−1.4 (4)
C1—C2—C3—C40.4 (4)O3—C12—C13—O41.9 (4)
O1—C3—C4—C5−179.8 (3)C11—C12—C13—O4−177.3 (3)
C2—C3—C4—C5−0.4 (4)O3—C12—C13—C14−179.6 (3)
C3—C4—C5—C6−0.3 (4)C11—C12—C13—C141.1 (4)
C4—C5—C6—C10.8 (4)O4—C13—C14—O5−0.7 (4)
C4—C5—C6—C7−179.7 (3)C12—C13—C14—O5−179.2 (2)
C2—C1—C6—C5−0.7 (4)O4—C13—C14—C15178.0 (3)
C2—C1—C6—C7179.8 (3)C12—C13—C14—C15−0.5 (4)
C5—C6—C7—O2−9.0 (4)O5—C14—C15—C10178.7 (2)
C1—C6—C7—O2170.5 (3)C13—C14—C15—C100.1 (4)
C5—C6—C7—C8170.6 (3)C11—C10—C15—C14−0.4 (4)
C1—C6—C7—C8−9.9 (4)C9—C10—C15—C14179.4 (3)
O2—C7—C8—C9−8.0 (4)C11—C12—O3—C16−3.3 (4)
C6—C7—C8—C9172.3 (3)C13—C12—O3—C16177.5 (3)
C7—C8—C9—C10178.8 (3)C14—C13—O4—C17101.8 (3)
C8—C9—C10—C15179.9 (3)C12—C13—O4—C17−79.7 (3)
C8—C9—C10—C11−0.3 (5)C15—C14—O5—C182.1 (4)
C15—C10—C11—C121.1 (4)C13—C14—O5—C18−179.3 (3)
C9—C10—C11—C12−178.8 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.931.832.660 (3)147
C2—H2···Cg1ii0.932.723.536 (3)147
Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x, −y+1/2, z−1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.931.832.660 (3)147
C2—H2···Cg1ii0.932.723.536 (3)147
Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x, −y+1/2, z−1/2.
Acknowledgements top

HJR and SMD thank DAE-BRNS for financial assistance.

references
References top

Bruker (1999). SMART, SAINT and SADABS. 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–?.

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.

Kiran, A. J., Mithun, A., Holla, B. S., Shashikala, H. D., Umesh, G. & Chandrasekharan, K. (2007). Opt. Commun. 269, 235–240.

Ng, S.-L., Patil, P. S., Razak, I. A., Fun, H.-K. & Dharmaprakash, S. M. (2006). Acta Cryst. E62, o1228–o1230.

Ng, S.-L., Razak, I. A., Fun, H.-K., Patil, P. S. & Dharmaprakash, S. M. (2006). Acta Cryst. E62, o4650–o4652.

Ng, S.-L., Razak, I. A., Fun, H.-K., Patil, P. S., Dharmaprakash, S. M. & Shettigar, V. (2006). Acta Cryst. E62, o2611–o2613.

Patil, P. S., Ng, S.-L., Razak, I. A., Fun, H.-K. & Dharmaprakash, S. M. (2006). Acta Cryst. E62, o4448–o4449.

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.

Teh, J. B.-J., Patil, P. S., Fun, H.-K., Razak, I. A. & Dharmaprakash, S. M. (2006). Acta Cryst. E62, o890–o892.

Uchida, T., Kozawa, K., Sakai, T., Aoki, M., Yoguchi, H., Abduryim, A. & Watanabe, Y. (1998). Mol. Cryst. Liq. Cryst. 315, 135–140.

Vogel, A. I. (1999). Vogel's Textbook of Practical Organic Chemistry, 5th ed., edited by A. I. Vogel, B. S. Furniss, A. J. Hannaford, P. W. G. Smith & A. R.Tatchell, p. 1033. London: Longman Group.

Wu, H., Xu, Z. & Liang, Y.-M. (2005). Acta Cryst. E61, o1434–o1435.

Zhao, B., Lu, W.-Q., Zhoua, Z.-H. & Wu, Y. (2000). J. Mater. Chem. 10, 1513–1517.