Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807024038/lw2015sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807024038/lw2015Isup2.hkl |
CCDC reference: 651456
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C)= 0.004 Å
- R factor = 0.066
- wR factor = 0.179
- Data-to-parameter ratio = 14.6
checkCIF/PLATON results
No syntax errors found No errors found in this datablock
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).
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.
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.
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).
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).
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).
C18H18O5 | F(000) = 664 |
Mr = 314.32 | Dx = 1.322 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 853 reflections |
a = 12.4431 (18) Å | θ = 4.7–25.1° |
b = 8.5528 (12) Å | µ = 0.10 mm−1 |
c = 15.470 (2) Å | T = 295 K |
β = 106.399 (2)° | Block, pale yellow |
V = 1579.4 (4) Å3 | 0.25 × 0.20 × 0.20 mm |
Z = 4 |
Bruker SMART1000 CCD diffractometer | 3088 independent reflections |
Radiation source: fine-focus sealed tube | 1656 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.057 |
ω scans | θmax = 26.0°, θmin = 4.7° |
Absorption correction: multi-scan (SADABS; Bruker, 1999) | h = −15→8 |
Tmin = 0.960, Tmax = 0.981 | k = −7→10 |
7097 measured reflections | l = −18→19 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.066 | Hydrogen site location: difmap and geom |
wR(F2) = 0.179 | H-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 parameters | Δρmax = 0.33 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
C18H18O5 | V = 1579.4 (4) Å3 |
Mr = 314.32 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.4431 (18) Å | µ = 0.10 mm−1 |
b = 8.5528 (12) Å | T = 295 K |
c = 15.470 (2) Å | 0.25 × 0.20 × 0.20 mm |
β = 106.399 (2)° |
Bruker SMART1000 CCD diffractometer | 3088 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1999) | 1656 reflections with I > 2σ(I) |
Tmin = 0.960, Tmax = 0.981 | Rint = 0.057 |
7097 measured reflections |
R[F2 > 2σ(F2)] = 0.066 | 0 restraints |
wR(F2) = 0.179 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.33 e Å−3 |
3088 reflections | Δρmin = −0.20 e Å−3 |
211 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.3208 (2) | 0.4896 (3) | 0.30271 (17) | 0.0493 (7) | |
H1A | 0.2754 | 0.4203 | 0.3228 | 0.059* | |
C2 | 0.3227 (2) | 0.4838 (3) | 0.21394 (17) | 0.0522 (7) | |
H2 | 0.2788 | 0.4112 | 0.1747 | 0.063* | |
C3 | 0.3899 (2) | 0.5859 (3) | 0.18339 (16) | 0.0480 (7) | |
C4 | 0.4558 (2) | 0.6933 (4) | 0.24210 (18) | 0.0518 (7) | |
H4 | 0.5014 | 0.7618 | 0.2218 | 0.062* | |
C5 | 0.4535 (2) | 0.6982 (3) | 0.33056 (17) | 0.0495 (7) | |
H5 | 0.4982 | 0.7703 | 0.3696 | 0.059* | |
C6 | 0.3858 (2) | 0.5978 (3) | 0.36287 (16) | 0.0436 (7) | |
C7 | 0.3856 (2) | 0.6078 (3) | 0.45843 (17) | 0.0485 (7) | |
C8 | 0.3021 (3) | 0.5194 (4) | 0.48890 (18) | 0.0557 (8) | |
H8 | 0.2450 | 0.4685 | 0.4462 | 0.067* | |
C9 | 0.3050 (2) | 0.5093 (4) | 0.57539 (18) | 0.0519 (7) | |
H9 | 0.3643 | 0.5603 | 0.6158 | 0.062* | |
C10 | 0.2269 (2) | 0.4285 (3) | 0.61475 (17) | 0.0483 (7) | |
C11 | 0.1338 (2) | 0.3478 (4) | 0.56173 (18) | 0.0540 (8) | |
H11 | 0.1209 | 0.3429 | 0.4996 | 0.065* | |
C12 | 0.0609 (2) | 0.2754 (4) | 0.60208 (19) | 0.0536 (8) | |
C13 | 0.0808 (2) | 0.2791 (3) | 0.69571 (18) | 0.0511 (7) | |
C14 | 0.1739 (2) | 0.3589 (3) | 0.74823 (16) | 0.0487 (7) | |
C15 | 0.2463 (2) | 0.4328 (3) | 0.70822 (17) | 0.0491 (7) | |
H15 | 0.3084 | 0.4857 | 0.7438 | 0.059* | |
C16 | −0.0614 (3) | 0.1908 (4) | 0.4622 (2) | 0.0831 (11) | |
H16A | −0.1310 | 0.1363 | 0.4386 | 0.125* | |
H16B | −0.0034 | 0.1380 | 0.4439 | 0.125* | |
H16C | −0.0687 | 0.2959 | 0.4395 | 0.125* | |
C17 | −0.0895 (3) | 0.2857 (5) | 0.7318 (2) | 0.0783 (10) | |
H17A | −0.1324 | 0.2294 | 0.7643 | 0.118* | |
H17B | −0.1326 | 0.2965 | 0.6700 | 0.118* | |
H17C | −0.0713 | 0.3875 | 0.7581 | 0.118* | |
C18 | 0.2756 (3) | 0.4307 (5) | 0.89628 (19) | 0.0819 (12) | |
H18A | 0.2731 | 0.4176 | 0.9573 | 0.123* | |
H18B | 0.2713 | 0.5400 | 0.8815 | 0.123* | |
H18C | 0.3444 | 0.3884 | 0.8900 | 0.123* | |
O1 | 0.3881 (2) | 0.5740 (3) | 0.09582 (12) | 0.0697 (7) | |
H1 | 0.4368 | 0.6355 | 0.0742 | 0.084* | |
O2 | 0.45533 (17) | 0.6910 (3) | 0.51111 (12) | 0.0603 (6) | |
O3 | −0.03409 (19) | 0.1939 (3) | 0.55607 (14) | 0.0720 (7) | |
O4 | 0.01136 (18) | 0.2021 (3) | 0.73646 (13) | 0.0642 (6) | |
O5 | 0.18695 (18) | 0.3539 (3) | 0.83935 (12) | 0.0628 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0551 (17) | 0.0436 (18) | 0.0499 (15) | −0.0043 (14) | 0.0161 (13) | 0.0026 (12) |
C2 | 0.0619 (18) | 0.0421 (18) | 0.0490 (15) | −0.0073 (15) | 0.0097 (14) | −0.0030 (12) |
C3 | 0.0564 (17) | 0.0438 (17) | 0.0420 (14) | 0.0032 (14) | 0.0110 (13) | 0.0038 (12) |
C4 | 0.0531 (16) | 0.0484 (19) | 0.0519 (16) | −0.0040 (14) | 0.0119 (13) | 0.0067 (13) |
C5 | 0.0512 (16) | 0.0461 (18) | 0.0467 (14) | −0.0048 (14) | 0.0062 (12) | −0.0021 (12) |
C6 | 0.0442 (14) | 0.0411 (17) | 0.0437 (13) | 0.0049 (13) | 0.0098 (12) | 0.0024 (12) |
C7 | 0.0501 (16) | 0.0484 (18) | 0.0469 (14) | 0.0090 (14) | 0.0135 (13) | −0.0009 (13) |
C8 | 0.0549 (17) | 0.061 (2) | 0.0496 (16) | −0.0004 (16) | 0.0114 (14) | −0.0013 (14) |
C9 | 0.0556 (17) | 0.0503 (18) | 0.0491 (15) | 0.0059 (15) | 0.0137 (14) | −0.0006 (13) |
C10 | 0.0548 (16) | 0.0439 (18) | 0.0465 (15) | 0.0090 (14) | 0.0146 (13) | 0.0032 (12) |
C11 | 0.0608 (17) | 0.057 (2) | 0.0417 (14) | 0.0041 (16) | 0.0107 (13) | 0.0013 (13) |
C12 | 0.0546 (17) | 0.0496 (19) | 0.0520 (15) | 0.0019 (15) | 0.0077 (13) | −0.0012 (13) |
C13 | 0.0540 (16) | 0.0469 (18) | 0.0530 (16) | 0.0065 (15) | 0.0163 (14) | 0.0063 (13) |
C14 | 0.0571 (16) | 0.0474 (18) | 0.0405 (14) | 0.0129 (15) | 0.0120 (13) | 0.0030 (12) |
C15 | 0.0514 (16) | 0.0450 (18) | 0.0489 (15) | 0.0022 (14) | 0.0107 (13) | −0.0021 (12) |
C16 | 0.079 (2) | 0.079 (3) | 0.072 (2) | −0.008 (2) | −0.0092 (18) | −0.0128 (18) |
C17 | 0.064 (2) | 0.095 (3) | 0.084 (2) | 0.000 (2) | 0.0335 (18) | 0.008 (2) |
C18 | 0.117 (3) | 0.085 (3) | 0.0390 (16) | −0.009 (2) | 0.0151 (18) | −0.0043 (16) |
O1 | 0.0941 (17) | 0.0699 (16) | 0.0458 (11) | −0.0159 (13) | 0.0208 (11) | 0.0009 (9) |
O2 | 0.0637 (13) | 0.0664 (15) | 0.0508 (11) | −0.0055 (11) | 0.0159 (10) | −0.0122 (10) |
O3 | 0.0737 (14) | 0.0739 (17) | 0.0663 (13) | −0.0146 (13) | 0.0162 (11) | −0.0057 (11) |
O4 | 0.0677 (13) | 0.0592 (15) | 0.0684 (13) | −0.0011 (12) | 0.0236 (11) | 0.0114 (10) |
O5 | 0.0721 (14) | 0.0710 (15) | 0.0460 (10) | 0.0003 (12) | 0.0179 (10) | 0.0016 (10) |
C1—C2 | 1.381 (4) | C11—H11 | 0.9300 |
C1—C6 | 1.397 (4) | C12—O3 | 1.384 (3) |
C1—H1A | 0.9300 | C12—C13 | 1.399 (4) |
C2—C3 | 1.381 (4) | C13—O4 | 1.373 (3) |
C2—H2 | 0.9300 | C13—C14 | 1.392 (4) |
C3—O1 | 1.352 (3) | C14—O5 | 1.373 (3) |
C3—C4 | 1.386 (4) | C14—C15 | 1.382 (4) |
C4—C5 | 1.377 (4) | C15—H15 | 0.9300 |
C4—H4 | 0.9300 | C16—O3 | 1.395 (4) |
C5—C6 | 1.391 (4) | C16—H16A | 0.9600 |
C5—H5 | 0.9300 | C16—H16B | 0.9600 |
C6—C7 | 1.481 (4) | C16—H16C | 0.9600 |
C7—O2 | 1.235 (3) | C17—O4 | 1.429 (4) |
C7—C8 | 1.466 (4) | C17—H17A | 0.9600 |
C8—C9 | 1.331 (4) | C17—H17B | 0.9600 |
C8—H8 | 0.9300 | C17—H17C | 0.9600 |
C9—C10 | 1.458 (4) | C18—O5 | 1.369 (4) |
C9—H9 | 0.9300 | C18—H18A | 0.9600 |
C10—C15 | 1.398 (3) | C18—H18B | 0.9600 |
C10—C11 | 1.398 (4) | C18—H18C | 0.9600 |
C11—C12 | 1.384 (4) | O1—H1 | 0.9331 |
C2—C1—C6 | 121.1 (3) | O3—C12—C13 | 114.8 (3) |
C2—C1—H1A | 119.5 | C11—C12—C13 | 120.6 (3) |
C6—C1—H1A | 119.5 | O4—C13—C14 | 119.7 (2) |
C3—C2—C1 | 120.0 (3) | O4—C13—C12 | 120.9 (3) |
C3—C2—H2 | 120.0 | C14—C13—C12 | 119.4 (3) |
C1—C2—H2 | 120.0 | O5—C14—C15 | 124.8 (3) |
O1—C3—C2 | 117.0 (3) | O5—C14—C13 | 114.9 (3) |
O1—C3—C4 | 123.1 (3) | C15—C14—C13 | 120.2 (2) |
C2—C3—C4 | 119.9 (2) | C14—C15—C10 | 120.5 (3) |
C5—C4—C3 | 119.8 (3) | C14—C15—H15 | 119.7 |
C5—C4—H4 | 120.1 | C10—C15—H15 | 119.7 |
C3—C4—H4 | 120.1 | O3—C16—H16A | 109.5 |
C4—C5—C6 | 121.5 (3) | O3—C16—H16B | 109.5 |
C4—C5—H5 | 119.3 | H16A—C16—H16B | 109.5 |
C6—C5—H5 | 119.3 | O3—C16—H16C | 109.5 |
C5—C6—C1 | 117.7 (2) | H16A—C16—H16C | 109.5 |
C5—C6—C7 | 119.6 (2) | H16B—C16—H16C | 109.5 |
C1—C6—C7 | 122.6 (3) | O4—C17—H17A | 109.5 |
O2—C7—C8 | 121.0 (2) | O4—C17—H17B | 109.5 |
O2—C7—C6 | 119.6 (3) | H17A—C17—H17B | 109.5 |
C8—C7—C6 | 119.5 (3) | O4—C17—H17C | 109.5 |
C9—C8—C7 | 122.4 (3) | H17A—C17—H17C | 109.5 |
C9—C8—H8 | 118.8 | H17B—C17—H17C | 109.5 |
C7—C8—H8 | 118.8 | O5—C18—H18A | 109.5 |
C8—C9—C10 | 128.2 (3) | O5—C18—H18B | 109.5 |
C8—C9—H9 | 115.9 | H18A—C18—H18B | 109.5 |
C10—C9—H9 | 115.9 | O5—C18—H18C | 109.5 |
C15—C10—C11 | 119.5 (3) | H18A—C18—H18C | 109.5 |
C15—C10—C9 | 118.6 (3) | H18B—C18—H18C | 109.5 |
C11—C10—C9 | 121.9 (2) | C3—O1—H1 | 119.2 |
C12—C11—C10 | 119.8 (2) | C12—O3—C16 | 117.8 (3) |
C12—C11—H11 | 120.1 | C13—O4—C17 | 113.3 (2) |
C10—C11—H11 | 120.1 | C18—O5—C14 | 119.1 (2) |
O3—C12—C11 | 124.5 (3) | ||
C6—C1—C2—C3 | 0.1 (4) | C10—C11—C12—O3 | 179.4 (3) |
C1—C2—C3—O1 | 179.9 (3) | C10—C11—C12—C13 | −1.4 (4) |
C1—C2—C3—C4 | 0.4 (4) | O3—C12—C13—O4 | 1.9 (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—C14 | 1.1 (4) |
C4—C5—C6—C1 | 0.8 (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—C15 | 178.0 (3) |
C2—C1—C6—C7 | 179.8 (3) | C12—C13—C14—C15 | −0.5 (4) |
C5—C6—C7—O2 | −9.0 (4) | O5—C14—C15—C10 | 178.7 (2) |
C1—C6—C7—O2 | 170.5 (3) | C13—C14—C15—C10 | 0.1 (4) |
C5—C6—C7—C8 | 170.6 (3) | C11—C10—C15—C14 | −0.4 (4) |
C1—C6—C7—C8 | −9.9 (4) | C9—C10—C15—C14 | 179.4 (3) |
O2—C7—C8—C9 | −8.0 (4) | C11—C12—O3—C16 | −3.3 (4) |
C6—C7—C8—C9 | 172.3 (3) | C13—C12—O3—C16 | 177.5 (3) |
C7—C8—C9—C10 | 178.8 (3) | C14—C13—O4—C17 | 101.8 (3) |
C8—C9—C10—C15 | 179.9 (3) | C12—C13—O4—C17 | −79.7 (3) |
C8—C9—C10—C11 | −0.3 (5) | C15—C14—O5—C18 | 2.1 (4) |
C15—C10—C11—C12 | 1.1 (4) | C13—C14—O5—C18 | −179.3 (3) |
C9—C10—C11—C12 | −178.8 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.93 | 1.83 | 2.660 (3) | 147 |
C2—H2···Cg1ii | 0.93 | 2.72 | 3.536 (3) | 147 |
Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x, −y+1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C18H18O5 |
Mr | 314.32 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 295 |
a, b, c (Å) | 12.4431 (18), 8.5528 (12), 15.470 (2) |
β (°) | 106.399 (2) |
V (Å3) | 1579.4 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.25 × 0.20 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART1000 CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 1999) |
Tmin, Tmax | 0.960, 0.981 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7097, 3088, 1656 |
Rint | 0.057 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.066, 0.179, 1.00 |
No. of reflections | 3088 |
No. of parameters | 211 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.33, −0.20 |
Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.93 | 1.83 | 2.660 (3) | 147 |
C2—H2···Cg1ii | 0.93 | 2.72 | 3.536 (3) | 147 |
Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x, −y+1/2, z−1/2. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register
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).