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access(E,E,E)-1,6-Bis(4-chlorophenyl)hexa-1,3,5-triene
aDepartmemt of Chemistry, Xinzhou Teachers University, Xinzhou, Shanxi 030006, People's Republic of China
*Correspondence e-mail: liubin@sxu.edu.cn
The title molecule, C18H14Cl2, lies about an inversion centre. The hexatriene chain is planar with a maximum deviation of 0.0001 (17) Å. The torsion angle of the single bond between the chain and the benzene ring is −168.49 (17)°. In the crystal, the shortest intermolecular distance between the Cl atoms is 4.0785 (11) Å.
Related literature
For the preparation, see: Spangler et al. (1989![[Spangler, C. W., McCoy, R. K., Dembek, A. A., Sapochak, L. S. & Gates, B. D. (1989). J. Chem. Soc. Perkin Trans 1, pp. 151-154.]](../../../../../../logos/arrows/e_arr.gif "Spangler, C. W., McCoy, R. K., Dembek, A. A., Sapochak, L. S. & Gates, B. D. (1989). J. Chem. Soc. Perkin Trans 1, pp. 151-154.")
). For luminescence and fluorescent properties of trans-diphenyl polyenes, see: Alford & Palmer (1986); Sonoda et al.(2003).
![[Scheme 1]](go2085scheme1.gif)
Experimental
Crystal data
|
Data collection: CrysAlis PRO (Agilent, 2012); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007); program(s) used to refine structure: OLEX2 (Dolomanov et al., 2009) and SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2; software used to prepare material for publication: OLEX2.
Supporting information
contains datablocks I, global. DOI: https://doi.org/10.1107/S160053681300932X/go2085sup1.cif
Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681300932X/go2085Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S160053681300932X/go2085Isup3.cml
The compound was prepared and purified as described previously (Spangler et al.1989). Crystals suitable for the X-ray diffraction study was obtained free evaporation of an solvent chloroform from a highly diluted solution in the dark at room temperature.
H atoms attached to C atoms were placed in geometrically idealized positions with Csp2 = 0.930 Å,and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq.
The luminescence properties of the linear all-trans-diphenyl polyenes Ph-(CH=CH)n—Ph (DPH) have been the subject of numerous investigations(Sonoda et al.(2003)). The emission properties of DPH and its derivatives in solution have been extensively studied because of its unique fluorescence behavior(Alford & Palmer,1986). DPH is known to exhibit dual fluorescence from S1 and S2 at thermal equilibrium. The of (E,E,E)-1,6-bis(2,4-dichlorophenyl)hexa-1,3,5-triene has been studied (Sonoda et al.2003). In the of the related compound, E,E,E-1,6-bis(p-chlorophenyl)- 1,3,5-hexatriene, the benzene rings are π···π stacked with unit translation along the b-axis with a centroid to centroid distance of 4.0785 (11)Å, a perpendicular distance between the planes of 3.4728 (8)Å and a slippage of 2.139Å.
For the preparation, see: Spangler et al. (1989). For luminescence and fluorescent properties of trans-diphenyl polyenes, see: Alford & Palmer (1986); Sonoda et al.(2003).
Data collection: CrysAlis PRO (Agilent, 2012); cell CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007); program(s) used to refine structure: OLEX2 (Dolomanov et al., 2009) and SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).
![[Figure 1]](./go2085fig1thm.gif) | Fig. 1. The structure of the title compound in 30% probability ellipsoids. H atoms are shown as small spheres of arbitrary radii. |
| C18H14Cl2 | F(000) = 312 |
| Mr = 301.19 | Dx = 1.348 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.7107 Å |
| Hall symbol: -P 2ybc | Cell parameters from 971 reflections |
| a = 15.6277 (7) Å | θ = 3.4–28.6° |
| b = 4.0784 (2) Å | µ = 0.42 mm−1 |
| c = 12.1026 (5) Å | T = 291 K |
| β = 105.810 (4)° | Block, yellow |
| V = 742.20 (5) Å3 | 0.42 × 0.38 × 0.30 mm |
| Z = 2 |
| Agilent SuperNova (Dual, Cu at zero, Eos) diffractometer | 1560 independent reflections |
| Radiation source: SuperNova (Mo) X-ray Source | 1214 reflections with I > 2σ(I) |
| Mirror monochromator | Rint = 0.013 |
| Detector resolution: 16.0733 pixels mm-1 | θmax = 26.7°, θmin = 3.4° |
| ω scans | h = −11→19 |
| Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) | k = −4→5 |
| Tmin = 0.667, Tmax = 1.000 | l = −15→15 |
| 2513 measured reflections |
| 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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.105 | H-atom parameters constrained |
| S = 1.06 | w = 1/[σ2(Fo2) + (0.0404P)2 + 0.1061P] where P = (Fo2 + 2Fc2)/3 |
| 1560 reflections | (Δ/σ)max = 0.001 |
| 91 parameters | Δρmax = 0.17 e Å−3 |
| 0 restraints | Δρmin = −0.21 e Å−3 |
| C18H14Cl2 | V = 742.20 (5) Å3 |
| Mr = 301.19 | Z = 2 |
| Monoclinic, P21/c | Mo Kα radiation |
| a = 15.6277 (7) Å | µ = 0.42 mm−1 |
| b = 4.0784 (2) Å | T = 291 K |
| c = 12.1026 (5) Å | 0.42 × 0.38 × 0.30 mm |
| β = 105.810 (4)° |
| Agilent SuperNova (Dual, Cu at zero, Eos) diffractometer | 1560 independent reflections |
| Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) | 1214 reflections with I > 2σ(I) |
| Tmin = 0.667, Tmax = 1.000 | Rint = 0.013 |
| 2513 measured reflections |
| R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
| wR(F2) = 0.105 | H-atom parameters constrained |
| S = 1.06 | Δρmax = 0.17 e Å−3 |
| 1560 reflections | Δρmin = −0.21 e Å−3 |
| 91 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
| x | y | z | Uiso*/Ueq | ||
| Cl1 | 0.94481 (3) | 0.31466 (16) | 0.62511 (5) | 0.0747 (3) | |
| C1 | 0.70850 (12) | 0.6448 (4) | 0.44590 (15) | 0.0465 (4) | |
| H1 | 0.6623 | 0.7651 | 0.4608 | 0.056* | |
| C2 | 0.70013 (10) | 0.5327 (4) | 0.33486 (14) | 0.0396 (4) | |
| C3 | 0.61893 (11) | 0.6044 (4) | 0.24400 (15) | 0.0440 (4) | |
| H3 | 0.5806 | 0.7576 | 0.2617 | 0.053* | |
| C4 | 0.59348 (11) | 0.4758 (4) | 0.13885 (14) | 0.0428 (4) | |
| H4 | 0.6301 | 0.3187 | 0.1196 | 0.051* | |
| C5 | 0.51318 (11) | 0.5638 (4) | 0.05308 (14) | 0.0442 (4) | |
| H5 | 0.4768 | 0.7210 | 0.0727 | 0.053* | |
| C6 | 0.78361 (12) | 0.5819 (4) | 0.53446 (15) | 0.0491 (5) | |
| H6 | 0.7879 | 0.6593 | 0.6081 | 0.059* | |
| C7 | 0.84667 (12) | 0.2943 (5) | 0.40343 (16) | 0.0512 (5) | |
| H7 | 0.8936 | 0.1769 | 0.3892 | 0.061* | |
| C8 | 0.77155 (11) | 0.3594 (4) | 0.31545 (15) | 0.0462 (4) | |
| H8 | 0.7685 | 0.2863 | 0.2417 | 0.055* | |
| C9 | 0.85169 (11) | 0.4047 (4) | 0.51293 (15) | 0.0473 (4) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cl1 | 0.0578 (3) | 0.0907 (5) | 0.0617 (4) | 0.0025 (3) | −0.0072 (2) | 0.0067 (3) |
| C1 | 0.0474 (10) | 0.0494 (10) | 0.0469 (10) | 0.0036 (8) | 0.0197 (8) | −0.0014 (9) |
| C2 | 0.0397 (8) | 0.0400 (9) | 0.0410 (9) | −0.0025 (7) | 0.0141 (7) | 0.0023 (8) |
| C3 | 0.0416 (9) | 0.0438 (10) | 0.0492 (10) | 0.0039 (7) | 0.0166 (8) | 0.0027 (8) |
| C4 | 0.0401 (8) | 0.0418 (9) | 0.0475 (10) | 0.0008 (7) | 0.0137 (7) | 0.0052 (8) |
| C5 | 0.0399 (9) | 0.0445 (10) | 0.0492 (9) | 0.0010 (7) | 0.0135 (7) | 0.0071 (8) |
| C6 | 0.0569 (11) | 0.0522 (11) | 0.0392 (9) | −0.0052 (9) | 0.0145 (8) | −0.0021 (8) |
| C7 | 0.0406 (9) | 0.0593 (12) | 0.0542 (11) | 0.0056 (8) | 0.0137 (8) | 0.0018 (10) |
| C8 | 0.0458 (9) | 0.0535 (11) | 0.0408 (9) | 0.0003 (8) | 0.0144 (7) | −0.0047 (8) |
| C9 | 0.0432 (9) | 0.0486 (10) | 0.0462 (10) | −0.0058 (8) | 0.0054 (7) | 0.0060 (9) |
| Cl1—C9 | 1.7376 (17) | C4—H4 | 0.9300 |
| C1—C6 | 1.381 (2) | C5—C5i | 1.342 (3) |
| C1—C2 | 1.392 (2) | C5—H5 | 0.9300 |
| C1—H1 | 0.9300 | C6—C9 | 1.369 (2) |
| C2—C8 | 1.394 (2) | C6—H6 | 0.9300 |
| C2—C3 | 1.464 (2) | C7—C8 | 1.379 (2) |
| C3—C4 | 1.333 (2) | C7—C9 | 1.382 (3) |
| C3—H3 | 0.9300 | C7—H7 | 0.9300 |
| C4—C5 | 1.439 (2) | C8—H8 | 0.9300 |
| C6—C1—C2 | 121.66 (16) | C4—C5—H5 | 117.5 |
| C6—C1—H1 | 119.2 | C9—C6—C1 | 119.39 (17) |
| C2—C1—H1 | 119.2 | C9—C6—H6 | 120.3 |
| C1—C2—C8 | 117.41 (15) | C1—C6—H6 | 120.3 |
| C1—C2—C3 | 119.58 (15) | C8—C7—C9 | 119.45 (17) |
| C8—C2—C3 | 122.99 (15) | C8—C7—H7 | 120.3 |
| C4—C3—C2 | 127.62 (16) | C9—C7—H7 | 120.3 |
| C4—C3—H3 | 116.2 | C7—C8—C2 | 121.33 (17) |
| C2—C3—H3 | 116.2 | C7—C8—H8 | 119.3 |
| C3—C4—C5 | 124.43 (17) | C2—C8—H8 | 119.3 |
| C3—C4—H4 | 117.8 | C6—C9—C7 | 120.72 (17) |
| C5—C4—H4 | 117.8 | C6—C9—Cl1 | 119.46 (15) |
| C5i—C5—C4 | 125.0 (2) | C7—C9—Cl1 | 119.81 (14) |
| C5i—C5—H5 | 117.5 | ||
| C6—C1—C2—C8 | −1.4 (3) | C9—C7—C8—C2 | −0.5 (3) |
| C6—C1—C2—C3 | 179.69 (16) | C1—C2—C8—C7 | 1.6 (3) |
| C1—C2—C3—C4 | −168.49 (17) | C3—C2—C8—C7 | −179.46 (16) |
| C8—C2—C3—C4 | 12.6 (3) | C1—C6—C9—C7 | 1.3 (3) |
| C2—C3—C4—C5 | −178.71 (16) | C1—C6—C9—Cl1 | −178.05 (13) |
| C3—C4—C5—C5i | 180.0 (2) | C8—C7—C9—C6 | −1.0 (3) |
| C2—C1—C6—C9 | −0.1 (3) | C8—C7—C9—Cl1 | 178.31 (14) |
| Symmetry code: (i) −x+1, −y+1, −z. |
Experimental details
| Crystal data | |
| Chemical formula | C18H14Cl2 |
| Mr | 301.19 |
| Crystal system, space group | Monoclinic, P21/c |
| Temperature (K) | 291 |
| a, b, c (Å) | 15.6277 (7), 4.0784 (2), 12.1026 (5) |
| β (°) | 105.810 (4) |
| V (Å3) | 742.20 (5) |
| Z | 2 |
| Radiation type | Mo Kα |
| µ (mm−1) | 0.42 |
| Crystal size (mm) | 0.42 × 0.38 × 0.30 |
| Data collection | |
| Diffractometer | Agilent SuperNova (Dual, Cu at zero, Eos) |
| Absorption correction | Multi-scan (CrysAlis PRO; Agilent, 2012) |
| Tmin, Tmax | 0.667, 1.000 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 2513, 1560, 1214 |
| Rint | 0.013 |
| (sin θ/λ)max (Å−1) | 0.633 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.105, 1.06 |
| No. of reflections | 1560 |
| No. of parameters | 91 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.17, −0.21 |
Computer programs: CrysAlis PRO (Agilent, 2012), SUPERFLIP (Palatinus & Chapuis, 2007), OLEX2 (Dolomanov et al., 2009) and SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).
Acknowledgements
We acknowledge the Scientific and Technological Development Project funding of colleges and universities in Shanxi Province (20111023)
References
Agilent (2012). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England. Google Scholar
Alford, P. C. & Palmer, T. F. (1986). Chem. Phys. Lett. 127, 19–25. CrossRef CAS Web of Science Google Scholar
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Spangler, C. W., McCoy, R. K., Dembek, A. A., Sapochak, L. S. & Gates, B. D. (1989). J. Chem. Soc. Perkin Trans 1, pp. 151–154. CrossRef Web of Science Google Scholar
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| CRYSTALLOGRAPHIC COMMUNICATIONS |
The luminescence properties of the linear all-trans-diphenyl polyenes Ph-(CH=CH)n—Ph (DPH) have been the subject of numerous investigations(Sonoda et al.(2003)). The emission properties of DPH and its derivatives in solution have been extensively studied because of its unique fluorescence behavior(Alford & Palmer,1986). DPH is known to exhibit dual fluorescence from S1 and S2 at thermal equilibrium. The crystal structure of (E,E,E)-1,6-bis(2,4-dichlorophenyl)hexa-1,3,5-triene has been studied (Sonoda et al.2003). In the crystal structure of the related compound, E,E,E-1,6-bis(p-chlorophenyl)- 1,3,5-hexatriene, the benzene rings are π···π stacked with unit translation along the b-axis with a centroid to centroid distance of 4.0785 (11)Å, a perpendicular distance between the planes of 3.4728 (8)Å and a slippage of 2.139Å.