supplementary materials
2-[(E)-2,5-Dimethoxybenzylidene]indan-1-one
An equivalent molar quantities of 2,5-dimethoxybenzaldehyde (4.40 g, 26.5 mmol)
and 1-indanone (3.5 g, 26.5 mmol) were dissolved in 25 ml e thanol, and then
heated at reflux. Pipyridine (1 ml) was added to the solution, and reflux was
continued for 5 h. The solution was cooled to room temperature, and the solid
products were filtered, and washed with ethanol (25 ml) to give yellow
crystals. [Yield: 5.79 g, 91%; m.p. 403 - 404 K]. IR (cm-1) 1689 (C=O), 1614
(C=C). 1H-NMR (CDCl3): 3.82 (3H, s, CH3O), 3.83 (3H, s, CH3O), 4.04
(2H, s, CH2), 6.83 (1H, d, J = 9 Hz), 6.94 (1H, dd, J1
= 1.8 Hz, J2 = 6 Hz), 7.23 (1H, d, J = 3 Hz), 7.40 (1H, dd, J =
7.2 Hz, J2 = 7.1 Hz), 7.54 (1H, d, J = 7.8 Hz), 7.6 (1H, d, J =
4.2 Hz), 7.9 (1H, d, J = 9 Hz), 8.1 (1H, s, CH=C).
All H atoms bonded to the C atoms were positioned geometrically, with C—H
distances in the range 0.93–0.97 Å, and refined using a riding
approximation model, with Uiso(H) = 1.5Ueq of the carrier
atom for methyl H and 1.2Ueq for the remaining H atoms. The
calculation of the Flack (Flack & Schwarzenbach, 1988) parameter was
suppressed by the use of the MERG 4 instruction in SHELXL97 (Sheldrick,
2008), as the lack of anomalous scatterers did not allow the
determination of
the absolute configuration from the X-ray measurements.
Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).
2-[(
E)-2,5-Dimethoxybenzylidene]indan-1-one
top
Crystal data top
| C18H16O3 | F(000) = 592 |
| Mr = 280.31 | Dx = 1.311 Mg m−3 |
| Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: P 2c -2n | Cell parameters from 598 reflections |
| a = 12.925 (3) Å | θ = 2.6–18.0° |
| b = 20.163 (5) Å | µ = 0.09 mm−1 |
| c = 5.451 (1) Å | T = 296 K |
| V = 1420.6 (5) Å3 | Prism, yellow |
| Z = 4 | 0.38 × 0.09 × 0.04 mm |
Data collection top
Bruker Kappa APEXII CCD area-detector
diffractometer | 856 reflections with I > 2σ(I) |
| Radiation source: sealed tube | Rint = 0.107 |
| graphite | θmax = 28.3°, θmin = 2.6° |
| φ and ω scans | h = −16→17 |
| 8980 measured reflections | k = −26→25 |
| 1944 independent reflections | l = −7→4 |
Refinement top
| 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)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.115 | H-atom parameters constrained |
| S = 0.97 | w = 1/[σ2(Fo2) + (0.037P)2]
where P = (Fo2 + 2Fc2)/3 |
| 1944 reflections | (Δ/σ)max < 0.001 |
| 192 parameters | Δρmax = 0.17 e Å−3 |
| 1 restraint | Δρmin = −0.16 e Å−3 |
Crystal data top
| C18H16O3 | V = 1420.6 (5) Å3 |
| Mr = 280.31 | Z = 4 |
| Orthorhombic, Pna21 | Mo Kα radiation |
| a = 12.925 (3) Å | µ = 0.09 mm−1 |
| b = 20.163 (5) Å | T = 296 K |
| c = 5.451 (1) Å | 0.38 × 0.09 × 0.04 mm |
Data collection top
Bruker Kappa APEXII CCD area-detector
diffractometer | 856 reflections with I > 2σ(I) |
| 8980 measured reflections | Rint = 0.107 |
| 1944 independent reflections | θmax = 28.3° |
Refinement top
| R[F2 > 2σ(F2)] = 0.055 | H-atom parameters constrained |
| wR(F2) = 0.115 | Δρmax = 0.17 e Å−3 |
| S = 0.97 | Δρmin = −0.16 e Å−3 |
| 1944 reflections | Absolute structure: ? |
| 192 parameters | Flack parameter: ? |
| 1 restraint | Rogers parameter: ? |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user
for potential systematic errors. Weighted R-factors wR and all
goodnesses of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The observed criterion of F2 > σ(F2)
is used only for calculating -R-factor-obs 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| | x | y | z | Uiso*/Ueq | |
| O1 | 0.4588 (2) | 0.22227 (16) | 0.5837 (6) | 0.0619 (13) | |
| O2 | 0.4627 (2) | 0.38576 (15) | 1.1861 (5) | 0.0507 (11) | |
| O3 | 0.8608 (2) | 0.47706 (17) | 1.0485 (6) | 0.0683 (16) | |
| C1 | 0.6059 (3) | 0.2111 (2) | 0.3166 (8) | 0.0400 (16) | |
| C2 | 0.5790 (3) | 0.1610 (2) | 0.1549 (9) | 0.0507 (17) | |
| C3 | 0.6488 (3) | 0.1442 (2) | −0.0268 (9) | 0.0533 (17) | |
| C4 | 0.7428 (4) | 0.1762 (2) | −0.0452 (8) | 0.0553 (19) | |
| C5 | 0.7699 (3) | 0.2264 (2) | 0.1200 (8) | 0.0460 (17) | |
| C6 | 0.6999 (3) | 0.2433 (2) | 0.3014 (7) | 0.0360 (14) | |
| C7 | 0.7111 (3) | 0.2962 (2) | 0.4948 (7) | 0.0347 (14) | |
| C8 | 0.6098 (3) | 0.2932 (2) | 0.6309 (7) | 0.0350 (14) | |
| C9 | 0.5446 (3) | 0.2392 (2) | 0.5186 (7) | 0.0423 (16) | |
| C10 | 0.5726 (3) | 0.3277 (2) | 0.8213 (8) | 0.0357 (14) | |
| C11 | 0.6191 (3) | 0.3804 (2) | 0.9655 (7) | 0.0327 (14) | |
| C12 | 0.5612 (3) | 0.4089 (2) | 1.1572 (7) | 0.0353 (14) | |
| C13 | 0.6046 (3) | 0.4569 (2) | 1.3073 (8) | 0.0423 (17) | |
| C14 | 0.7049 (3) | 0.4787 (2) | 1.2631 (8) | 0.0450 (17) | |
| C15 | 0.7623 (3) | 0.4521 (2) | 1.0747 (9) | 0.0430 (17) | |
| C16 | 0.7202 (3) | 0.4039 (2) | 0.9271 (7) | 0.0393 (16) | |
| C17 | 0.4010 (3) | 0.4138 (2) | 1.3758 (8) | 0.0570 (19) | |
| C18 | 0.9112 (3) | 0.4649 (3) | 0.8234 (10) | 0.072 (2) | |
| H2 | 0.51570 | 0.13930 | 0.16830 | 0.0600* | |
| H3 | 0.63220 | 0.11080 | −0.13810 | 0.0640* | |
| H4 | 0.78880 | 0.16430 | −0.16890 | 0.0670* | |
| H5 | 0.83340 | 0.24790 | 0.10800 | 0.0550* | |
| H7A | 0.76870 | 0.28660 | 0.60320 | 0.0410* | |
| H7B | 0.72130 | 0.33940 | 0.42110 | 0.0410* | |
| H10 | 0.50600 | 0.31600 | 0.86900 | 0.0430* | |
| H13 | 0.56670 | 0.47460 | 1.43690 | 0.0500* | |
| H14 | 0.73350 | 0.51150 | 1.36190 | 0.0540* | |
| H16 | 0.75940 | 0.38640 | 0.79940 | 0.0470* | |
| H17A | 0.43230 | 0.40480 | 1.53210 | 0.0860* | |
| H17B | 0.33300 | 0.39470 | 1.37100 | 0.0860* | |
| H17C | 0.39610 | 0.46090 | 1.35240 | 0.0860* | |
| H18A | 0.92540 | 0.41830 | 0.80830 | 0.1070* | |
| H18B | 0.97500 | 0.48920 | 0.81820 | 0.1070* | |
| H18C | 0.86750 | 0.47880 | 0.69060 | 0.1070* | |
Atomic displacement parameters (Å2) top| | U11 | U22 | U33 | U12 | U13 | U23 |
| O1 | 0.0348 (17) | 0.084 (3) | 0.067 (2) | −0.0157 (19) | 0.0072 (17) | −0.021 (2) |
| O2 | 0.0369 (17) | 0.064 (2) | 0.0512 (19) | −0.0076 (17) | 0.0123 (17) | −0.0217 (17) |
| O3 | 0.055 (2) | 0.084 (3) | 0.066 (3) | −0.0298 (19) | −0.003 (2) | −0.007 (2) |
| C1 | 0.050 (3) | 0.038 (3) | 0.032 (2) | 0.004 (2) | −0.007 (3) | −0.005 (3) |
| C2 | 0.054 (3) | 0.051 (3) | 0.047 (3) | −0.001 (2) | −0.010 (3) | −0.010 (3) |
| C3 | 0.062 (3) | 0.048 (3) | 0.050 (3) | 0.009 (3) | −0.003 (3) | −0.014 (3) |
| C4 | 0.063 (3) | 0.059 (4) | 0.044 (3) | 0.027 (3) | 0.005 (3) | −0.006 (3) |
| C5 | 0.047 (3) | 0.051 (3) | 0.040 (3) | 0.011 (2) | 0.002 (2) | −0.005 (3) |
| C6 | 0.034 (2) | 0.041 (3) | 0.033 (2) | 0.005 (2) | −0.001 (2) | 0.004 (2) |
| C7 | 0.036 (2) | 0.044 (3) | 0.024 (2) | 0.003 (2) | −0.0019 (19) | 0.003 (2) |
| C8 | 0.029 (2) | 0.042 (3) | 0.034 (2) | 0.001 (2) | −0.002 (2) | 0.002 (2) |
| C9 | 0.035 (2) | 0.052 (3) | 0.040 (3) | −0.002 (2) | −0.002 (2) | −0.003 (2) |
| C10 | 0.030 (2) | 0.050 (3) | 0.027 (2) | 0.000 (2) | 0.000 (2) | 0.003 (2) |
| C11 | 0.034 (2) | 0.036 (3) | 0.028 (2) | 0.001 (2) | −0.004 (2) | 0.001 (2) |
| C12 | 0.037 (2) | 0.038 (3) | 0.031 (2) | −0.001 (2) | −0.004 (2) | 0.001 (2) |
| C13 | 0.045 (3) | 0.043 (3) | 0.039 (3) | 0.007 (2) | −0.006 (3) | −0.004 (3) |
| C14 | 0.052 (3) | 0.041 (3) | 0.042 (3) | −0.007 (2) | −0.020 (3) | 0.005 (2) |
| C15 | 0.046 (3) | 0.043 (3) | 0.040 (3) | −0.013 (2) | −0.007 (2) | 0.003 (3) |
| C16 | 0.035 (2) | 0.046 (3) | 0.037 (3) | −0.003 (2) | 0.001 (2) | −0.001 (2) |
| C17 | 0.053 (3) | 0.069 (4) | 0.049 (3) | 0.000 (3) | 0.016 (2) | −0.014 (3) |
| C18 | 0.048 (3) | 0.104 (5) | 0.063 (4) | −0.023 (3) | −0.009 (3) | 0.027 (4) |
Geometric parameters (Å, °) top
| O1—C9 | 1.213 (5) | C13—C14 | 1.390 (6) |
| O2—C12 | 1.365 (5) | C14—C15 | 1.376 (6) |
| O2—C17 | 1.423 (5) | C15—C16 | 1.374 (6) |
| O3—C15 | 1.376 (5) | C2—H2 | 0.9300 |
| O3—C18 | 1.411 (6) | C3—H3 | 0.9300 |
| C1—C2 | 1.385 (6) | C4—H4 | 0.9300 |
| C1—C6 | 1.380 (6) | C5—H5 | 0.9300 |
| C1—C9 | 1.470 (6) | C7—H7A | 0.9700 |
| C2—C3 | 1.382 (6) | C7—H7B | 0.9700 |
| C3—C4 | 1.379 (6) | C10—H10 | 0.9300 |
| C4—C5 | 1.399 (6) | C13—H13 | 0.9300 |
| C5—C6 | 1.383 (6) | C14—H14 | 0.9300 |
| C6—C7 | 1.507 (6) | C16—H16 | 0.9300 |
| C7—C8 | 1.506 (5) | C17—H17A | 0.9600 |
| C8—C9 | 1.507 (6) | C17—H17B | 0.9600 |
| C8—C10 | 1.339 (6) | C17—H17C | 0.9600 |
| C10—C11 | 1.452 (6) | C18—H18A | 0.9600 |
| C11—C12 | 1.408 (5) | C18—H18B | 0.9600 |
| C11—C16 | 1.406 (6) | C18—H18C | 0.9600 |
| C12—C13 | 1.386 (6) | | |
| | | |
| O1···C7i | 3.259 (5) | C14···H17Cviii | 2.8600 |
| O2···C5ii | 3.384 (5) | C15···H17Cviii | 2.9600 |
| O2···C4ii | 3.351 (6) | C15···H7Bvii | 3.0000 |
| O1···H10 | 2.5200 | C16···H18C | 2.7500 |
| O1···H2 | 2.9100 | C16···H7B | 3.0500 |
| O1···H7Ai | 2.4700 | C16···H7A | 3.0200 |
| O2···H10 | 2.3000 | C16···H7Bvii | 2.9900 |
| O3···H18Biii | 2.6700 | C16···H18A | 2.7500 |
| C3···C8iv | 3.572 (6) | C17···H13 | 2.4900 |
| C3···C9iv | 3.409 (6) | C18···H16 | 2.5200 |
| C4···C7iv | 3.508 (6) | H2···O1 | 2.9100 |
| C4···C8iv | 3.411 (6) | H2···H18Ax | 2.5600 |
| C4···O2v | 3.351 (6) | H7A···C4vii | 2.9600 |
| C4···C17v | 3.569 (6) | H7A···C5vii | 3.0700 |
| C5···C17v | 3.579 (6) | H7A···C16 | 3.0200 |
| C5···O2v | 3.384 (5) | H7A···H16 | 2.2800 |
| C6···C11iv | 3.476 (6) | H7A···O1vi | 2.4700 |
| C6···C10iv | 3.529 (6) | H7B···C11iv | 2.9300 |
| C7···C11iv | 3.552 (6) | H7B···C12iv | 2.8800 |
| C7···O1vi | 3.259 (5) | H7B···C13iv | 2.8800 |
| C7···C16 | 3.207 (6) | H7B···C14iv | 2.9500 |
| C7···C4vii | 3.508 (6) | H7B···C15iv | 3.0000 |
| C7···C12iv | 3.508 (6) | H7B···C16iv | 2.9900 |
| C8···C12iv | 3.536 (6) | H7B···C16 | 3.0500 |
| C8···C4vii | 3.411 (6) | H7B···H16 | 2.3200 |
| C8···C3vii | 3.572 (6) | H10···O1 | 2.5200 |
| C9···C3vii | 3.409 (6) | H10···O2 | 2.3000 |
| C10···C6vii | 3.529 (6) | H13···C17 | 2.4900 |
| C11···C7vii | 3.552 (6) | H13···H17A | 2.3000 |
| C11···C6vii | 3.476 (6) | H13···H17C | 2.2700 |
| C12···C8vii | 3.536 (6) | H14···H18Cvii | 2.5800 |
| C12···C7vii | 3.508 (6) | H16···C7 | 2.5400 |
| C13···C17viii | 3.512 (6) | H16···C8 | 2.8500 |
| C14···C17viii | 3.321 (6) | H16···C18 | 2.5200 |
| C15···C17viii | 3.597 (6) | H16···H7A | 2.2800 |
| C16···C7 | 3.207 (6) | H16···H7B | 2.3200 |
| C17···C5ii | 3.579 (6) | H16···H18A | 2.2400 |
| C17···C15ix | 3.597 (6) | H16···H18C | 2.4000 |
| C17···C4ii | 3.569 (6) | H17A···C10vii | 2.8600 |
| C17···C13ix | 3.512 (6) | H17A···C13 | 2.7500 |
| C17···C14ix | 3.321 (6) | H17A···H13 | 2.3000 |
| C4···H7Aiv | 2.9600 | H17B···C4ii | 2.9200 |
| C4···H17Bv | 2.9200 | H17B···C5ii | 2.9200 |
| C5···H7Aiv | 3.0700 | H17C···C13 | 2.7100 |
| C5···H17Bv | 2.9200 | H17C···H13 | 2.2700 |
| C7···H16 | 2.5400 | H17C···C13ix | 2.9800 |
| C8···H16 | 2.8500 | H17C···C14ix | 2.8600 |
| C10···H17Aiv | 2.8600 | H17C···C15ix | 2.9600 |
| C11···H7Bvii | 2.9300 | H18A···C16 | 2.7500 |
| C12···H7Bvii | 2.8800 | H18A···H16 | 2.2400 |
| C13···H17A | 2.7500 | H18A···H2xi | 2.5600 |
| C13···H7Bvii | 2.8800 | H18B···O3xii | 2.6700 |
| C13···H17C | 2.7100 | H18C···C16 | 2.7500 |
| C13···H17Cviii | 2.9800 | H18C···H14iv | 2.5800 |
| C14···H7Bvii | 2.9500 | H18C···H16 | 2.4000 |
| | | |
| C12—O2—C17 | 118.1 (3) | C3—C2—H2 | 121.00 |
| C15—O3—C18 | 117.0 (4) | C2—C3—H3 | 120.00 |
| C2—C1—C6 | 121.7 (4) | C4—C3—H3 | 120.00 |
| C2—C1—C9 | 128.5 (4) | C3—C4—H4 | 120.00 |
| C6—C1—C9 | 109.8 (4) | C5—C4—H4 | 120.00 |
| C1—C2—C3 | 118.1 (4) | C4—C5—H5 | 121.00 |
| C2—C3—C4 | 120.8 (4) | C6—C5—H5 | 121.00 |
| C3—C4—C5 | 120.8 (4) | C6—C7—H7A | 111.00 |
| C4—C5—C6 | 118.3 (4) | C6—C7—H7B | 111.00 |
| C1—C6—C5 | 120.2 (4) | C8—C7—H7A | 111.00 |
| C1—C6—C7 | 112.1 (3) | C8—C7—H7B | 111.00 |
| C5—C6—C7 | 127.7 (4) | H7A—C7—H7B | 109.00 |
| C6—C7—C8 | 103.5 (3) | C8—C10—H10 | 115.00 |
| C7—C8—C9 | 108.4 (3) | C11—C10—H10 | 115.00 |
| C7—C8—C10 | 132.3 (4) | C12—C13—H13 | 120.00 |
| C9—C8—C10 | 119.3 (4) | C14—C13—H13 | 120.00 |
| O1—C9—C1 | 127.1 (4) | C13—C14—H14 | 120.00 |
| O1—C9—C8 | 126.6 (4) | C15—C14—H14 | 120.00 |
| C1—C9—C8 | 106.3 (3) | C11—C16—H16 | 119.00 |
| C8—C10—C11 | 130.6 (4) | C15—C16—H16 | 119.00 |
| C10—C11—C12 | 118.7 (4) | O2—C17—H17A | 109.00 |
| C10—C11—C16 | 123.4 (4) | O2—C17—H17B | 110.00 |
| C12—C11—C16 | 117.8 (4) | O2—C17—H17C | 109.00 |
| O2—C12—C11 | 116.2 (3) | H17A—C17—H17B | 110.00 |
| O2—C12—C13 | 123.2 (3) | H17A—C17—H17C | 109.00 |
| C11—C12—C13 | 120.5 (4) | H17B—C17—H17C | 109.00 |
| C12—C13—C14 | 119.7 (4) | O3—C18—H18A | 109.00 |
| C13—C14—C15 | 120.6 (4) | O3—C18—H18B | 109.00 |
| O3—C15—C14 | 115.7 (4) | O3—C18—H18C | 109.00 |
| O3—C15—C16 | 124.4 (4) | H18A—C18—H18B | 109.00 |
| C14—C15—C16 | 120.0 (4) | H18A—C18—H18C | 109.00 |
| C11—C16—C15 | 121.3 (4) | H18B—C18—H18C | 110.00 |
| C1—C2—H2 | 121.00 | | |
| | | |
| C17—O2—C12—C11 | −179.2 (3) | C6—C7—C8—C10 | −179.9 (4) |
| C17—O2—C12—C13 | 1.8 (6) | C7—C8—C9—O1 | 179.0 (4) |
| C18—O3—C15—C14 | −163.3 (4) | C7—C8—C9—C1 | −0.7 (4) |
| C18—O3—C15—C16 | 16.5 (6) | C10—C8—C9—O1 | −0.4 (6) |
| C6—C1—C2—C3 | −0.8 (6) | C10—C8—C9—C1 | 180.0 (4) |
| C9—C1—C2—C3 | 178.0 (4) | C7—C8—C10—C11 | −0.8 (8) |
| C2—C1—C6—C5 | 0.7 (6) | C9—C8—C10—C11 | 178.4 (4) |
| C2—C1—C6—C7 | 179.4 (4) | C8—C10—C11—C12 | 179.3 (4) |
| C9—C1—C6—C5 | −178.3 (4) | C8—C10—C11—C16 | −1.9 (7) |
| C9—C1—C6—C7 | 0.5 (5) | C10—C11—C12—O2 | −2.4 (5) |
| C2—C1—C9—O1 | 1.6 (7) | C10—C11—C12—C13 | 176.6 (4) |
| C2—C1—C9—C8 | −178.8 (4) | C16—C11—C12—O2 | 178.8 (3) |
| C6—C1—C9—O1 | −179.5 (4) | C16—C11—C12—C13 | −2.2 (6) |
| C6—C1—C9—C8 | 0.1 (5) | C10—C11—C16—C15 | −177.4 (4) |
| C1—C2—C3—C4 | 0.4 (6) | C12—C11—C16—C15 | 1.4 (6) |
| C2—C3—C4—C5 | 0.1 (7) | O2—C12—C13—C14 | −178.9 (4) |
| C3—C4—C5—C6 | −0.3 (6) | C11—C12—C13—C14 | 2.2 (6) |
| C4—C5—C6—C1 | −0.1 (6) | C12—C13—C14—C15 | −1.3 (6) |
| C4—C5—C6—C7 | −178.7 (4) | C13—C14—C15—O3 | −179.6 (4) |
| C1—C6—C7—C8 | −0.9 (4) | C13—C14—C15—C16 | 0.5 (6) |
| C5—C6—C7—C8 | 177.8 (4) | O3—C15—C16—C11 | 179.6 (4) |
| C6—C7—C8—C9 | 0.9 (4) | C14—C15—C16—C11 | −0.6 (6) |
| Symmetry codes: (i) x−1/2, −y+1/2, z; (ii) x−1/2, −y+1/2, z+1; (iii) −x+2, −y+1, z+1/2; (iv) x, y, z−1; (v) x+1/2, −y+1/2, z−1; (vi) x+1/2, −y+1/2, z; (vii) x, y, z+1; (viii) −x+1, −y+1, z−1/2; (ix) −x+1, −y+1, z+1/2; (x) x−1/2, −y+1/2, z−1; (xi) x+1/2, −y+1/2, z+1; (xii) −x+2, −y+1, z−1/2. |
Hydrogen-bond geometry (Å, °) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| C7—H7A···O1vi | 0.97 | 2.47 | 3.259 (5) | 139 |
| C10—H10···O1 | 0.93 | 2.52 | 2.891 (5) | 104 |
| C10—H10···O2 | 0.93 | 2.30 | 2.710 (5) | 106 |
| C7—H7B···Cg1iv | 0.97 | 2.59 | 3.459 (4) | 150 |
| C17—H17C···Cg1ix | 0.96 | 2.73 | 3.504 (4) | 138 |
| Symmetry codes: (vi) x+1/2, −y+1/2, z; (iv) x, y, z−1; (ix) −x+1, −y+1, z+1/2. |
Table 1
Hydrogen-bond geometry (Å, °) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| C7—H7A···O1i | 0.97 | 2.47 | 3.259 (5) | 139 |
| C10—H10···O1 | 0.93 | 2.52 | 2.891 (5) | 104 |
| C10—H10···O2 | 0.93 | 2.30 | 2.710 (5) | 106 |
| C7—H7B···Cg1ii | 0.97 | 2.59 | 3.459 (4) | 150 |
| C17—H17C···Cg1iii | 0.96 | 2.73 | 3.504 (4) | 138 |
| Symmetry codes: (i) x+1/2, −y+1/2, z; (ii) x, y, z−1; (iii) −x+1, −y+1, z+1/2. |
AMA acknowledges the Chemistry Department, Faculty of Science, King Abdul-Aziz
Universty, for providing the laboratories and facilities.
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O hydrogen contacts. The crystal structure is stabilized by intermolecular C-H![[pi]](/logos/entities/pi_rmgif.gif)
interactions are also observed.![[Figure 1]](./jh2077fig1thm.gif)
![[Figure 2]](./jh2077fig2thm.gif)
Nonlinear optical (NLO) properties of organics have been the subject of numerous investigations in the recent years, due to their potential applications in the field of photonics. A good NLO organic material should generally contain donor and acceptor groups positioned at either ends of a conjugation path of appropriate length. The increased effective conjugation and hence, the large π-delocalization length, has been recognized as a factor leading to large third order nonlinearities. Styryl dyes are organic molecules possessing charge donor and acceptor groups, conjugated through π-electronic bridge, suitable for NLO device applications. They are widely used as optical recording medium in laser disks, laser dyes (Ying et al., 1990) and optical sensitizers in various other fields (He et al., 1995).
In the title compound (I) (Fig. 1), all bond lengths (Allen et al., 1987) and angles are within normal ranges. The nine-membered indane ring is almost planar, with the maximum deviations of -0.017 (4) and 0.021 (4) Å for atoms C6 and C8, respectively. The mean plane of the indane ring makes a dihedral angle of 3.71 (17) °, with the benzene ring of the dimethoxy phenyl group.
The molecular conformation is stabilized by intramolecular C—H···O hydrogen contacts (Table 1). The crystal structure is stabilized by intermolecular C—H···O interactions, which link neighbouring molecules into 1-D extended chains along the [100] direction (Fig. 2). In the structure, C—H···π interactions are also observed (Table 1).