Acta Cryst. (2011). E67, o1478 [ doi:10.1107/S1600536811018538 ]
The molecule of the title compound, C22H26O2, exhibits Ci molecular symmetry with a crystallographic inversion centre at the mid-point of the central C-C bond. A kink in the molecule is defined by the torsion angle of 66.7 (2)° about this central bond of the alkyl bridge.
2-Propenylphenol (0.015 mol, 2 g) and KOH (0.015 mol, 0.84 g) were dissolved in 5 mL 2-propanol, then to this solution 1,4-dibromebutane (0.0043 mol, 0.93 g) was added. This mixture was stirred at 353 K within 30 min. The desired compounds (with yield of 4.7 g, 98.1%) was filtered and washed with acetone and recrystallised to obtain colourless crystals. Tmp = 353 K. The structure of the reported compound - 1,4-bis{2(1-propenyl)phenoxy}butane, also was proved by NMR-spectroscopy. FT-NMR (acetone-d6,, p.p.m.), 1H: 1.91 d (6H,CH3); 2.03 t (4H,CH2); 4.1 t (4H, OCH2); 6.15 m (2H, CH=); 6.65–7.1 m (8H, 2Ar); 7.32 d (2H,CH=). 13 C: 18.9; 26.3; 67.6; 112.8; 121.7; 124.9; 126.1; 127.2; 127.3; 127.5; 156.4.
The hydrogen atoms were placed in calculated positions and refined in the riding mode with fixed isotropic displacement parameters [Uiso(H) = 1.2Ueq(C)].
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
![[Figure 1]](./kp2326fig1thm.gif)
| Fig. 1. The molecular structure of the title compound with the atomic numbering scheme. Displacement ellipsoids were drawn at the 30% probability level. |
![[Figure 2]](./kp2326fig2thm.gif)
| Fig. 2. Stacking of chains in the crystal packing. |
| C22H26O2 | F(000) = 696 |
| Mr = 322.43 | Dx = 1.134 Mg m−3 |
| Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ac 2ab | Cell parameters from 4034 reflections |
| a = 5.4501 (10) Å | θ = 2.6–23.1° |
| b = 15.825 (3) Å | µ = 0.07 mm−1 |
| c = 21.889 (4) Å | T = 296 K |
| V = 1887.9 (6) Å3 | Prism, colourless |
| Z = 4 | 0.30 × 0.20 × 0.20 mm |
| Bruker SMART APEXII CCD diffractometer | 2404 independent reflections |
| Radiation source: fine-focus sealed tube | 1427 reflections with I > 2σ(I) |
| graphite | Rint = 0.040 |
| φ and ω scans | θmax = 28.6°, θmin = 1.9° |
| Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −7→7 |
| Tmin = 0.979, Tmax = 0.986 | k = −21→21 |
| 20262 measured reflections | l = −29→29 |
| 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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.151 | H-atom parameters constrained |
| S = 1.01 | w = 1/[σ2(Fo2) + (0.071P)2 + 0.2P] where P = (Fo2 + 2Fc2)/3 |
| 2404 reflections | (Δ/σ)max < 0.001 |
| 110 parameters | Δρmax = 0.15 e Å−3 |
| 0 restraints | Δρmin = −0.11 e Å−3 |
| C22H26O2 | V = 1887.9 (6) Å3 |
| Mr = 322.43 | Z = 4 |
| Orthorhombic, Pbca | Mo Kα radiation |
| a = 5.4501 (10) Å | µ = 0.07 mm−1 |
| b = 15.825 (3) Å | T = 296 K |
| c = 21.889 (4) Å | 0.30 × 0.20 × 0.20 mm |
| Bruker SMART APEXII CCD diffractometer | 2404 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 2001) | 1427 reflections with I > 2σ(I) |
| Tmin = 0.979, Tmax = 0.986 | Rint = 0.040 |
| 20262 measured reflections | θmax = 28.6° |
| R[F2 > 2σ(F2)] = 0.042 | H-atom parameters constrained |
| wR(F2) = 0.151 | Δρmax = 0.15 e Å−3 |
| S = 1.01 | Δρmin = −0.11 e Å−3 |
| 2404 reflections | Absolute structure: ? |
| 110 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
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 | ||
| O1 | 0.1929 (2) | 0.12834 (6) | 0.05285 (5) | 0.0764 (3) | |
| C1 | 0.1981 (3) | 0.19881 (9) | 0.08887 (6) | 0.0641 (4) | |
| C2 | 0.3717 (2) | 0.19780 (9) | 0.13598 (6) | 0.0614 (4) | |
| C3 | 0.3831 (3) | 0.26839 (11) | 0.17357 (8) | 0.0805 (5) | |
| H3A | 0.4969 | 0.2696 | 0.2052 | 0.097* | |
| C4 | 0.2297 (4) | 0.33659 (12) | 0.16510 (10) | 0.0964 (6) | |
| H4A | 0.2408 | 0.3832 | 0.1909 | 0.116* | |
| C5 | 0.0609 (4) | 0.33587 (12) | 0.11879 (11) | 0.0958 (6) | |
| H5A | −0.0436 | 0.3817 | 0.1134 | 0.115* | |
| C6 | 0.0455 (3) | 0.26750 (11) | 0.08014 (8) | 0.0826 (5) | |
| H6A | −0.0673 | 0.2675 | 0.0483 | 0.099* | |
| C7 | 0.5292 (3) | 0.12253 (10) | 0.14476 (7) | 0.0655 (4) | |
| H7A | 0.4863 | 0.0747 | 0.1225 | 0.079* | |
| C8 | 0.7203 (3) | 0.11548 (10) | 0.17993 (7) | 0.0729 (4) | |
| H8A | 0.7671 | 0.1632 | 0.2018 | 0.088* | |
| C9 | 0.8691 (3) | 0.03876 (12) | 0.18816 (7) | 0.0789 (5) | |
| H9A | 0.8709 | 0.0234 | 0.2306 | 0.118* | |
| H9B | 1.0338 | 0.0494 | 0.1746 | 0.118* | |
| H9C | 0.7998 | −0.0065 | 0.1646 | 0.118* | |
| C10 | 0.0059 (3) | 0.12144 (11) | 0.00726 (8) | 0.0791 (5) | |
| H10A | 0.0261 | 0.1653 | −0.0233 | 0.095* | |
| H10B | −0.1549 | 0.1277 | 0.0257 | 0.095* | |
| C11 | 0.0297 (4) | 0.03563 (11) | −0.02174 (7) | 0.0827 (5) | |
| H11A | 0.1962 | 0.0286 | −0.0366 | 0.099* | |
| H11B | −0.0797 | 0.0325 | −0.0566 | 0.099* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0798 (7) | 0.0745 (7) | 0.0750 (7) | 0.0052 (5) | −0.0182 (5) | −0.0066 (5) |
| C1 | 0.0641 (8) | 0.0616 (8) | 0.0665 (8) | −0.0057 (6) | 0.0061 (7) | 0.0056 (6) |
| C2 | 0.0609 (8) | 0.0622 (8) | 0.0611 (8) | −0.0133 (6) | 0.0091 (6) | 0.0018 (6) |
| C3 | 0.0864 (11) | 0.0742 (10) | 0.0807 (10) | −0.0152 (8) | 0.0078 (9) | −0.0079 (8) |
| C4 | 0.1190 (15) | 0.0636 (10) | 0.1066 (14) | −0.0128 (10) | 0.0252 (13) | −0.0162 (10) |
| C5 | 0.1026 (13) | 0.0663 (11) | 0.1185 (16) | 0.0098 (9) | 0.0153 (13) | 0.0074 (10) |
| C6 | 0.0802 (10) | 0.0741 (11) | 0.0936 (12) | 0.0050 (8) | 0.0000 (9) | 0.0135 (9) |
| C7 | 0.0640 (8) | 0.0719 (9) | 0.0605 (8) | −0.0116 (7) | −0.0001 (6) | −0.0039 (7) |
| C8 | 0.0725 (9) | 0.0806 (10) | 0.0657 (9) | −0.0124 (8) | −0.0047 (7) | −0.0068 (7) |
| C9 | 0.0681 (9) | 0.0978 (12) | 0.0708 (9) | 0.0015 (8) | −0.0044 (7) | 0.0010 (8) |
| C10 | 0.0803 (10) | 0.0902 (11) | 0.0666 (9) | −0.0064 (8) | −0.0164 (8) | 0.0109 (8) |
| C11 | 0.0945 (12) | 0.0979 (12) | 0.0558 (8) | −0.0157 (10) | −0.0108 (8) | 0.0026 (7) |
| O1—C1 | 1.3659 (17) | C7—C8 | 1.300 (2) |
| O1—C10 | 1.4305 (19) | C7—H7A | 0.9300 |
| C1—C6 | 1.382 (2) | C8—C9 | 1.471 (2) |
| C1—C2 | 1.399 (2) | C8—H8A | 0.9300 |
| C2—C3 | 1.389 (2) | C9—H9A | 0.9600 |
| C2—C7 | 1.481 (2) | C9—H9B | 0.9600 |
| C3—C4 | 1.378 (3) | C9—H9C | 0.9600 |
| C3—H3A | 0.9300 | C10—C11 | 1.505 (2) |
| C4—C5 | 1.369 (3) | C10—H10A | 0.9700 |
| C4—H4A | 0.9300 | C10—H10B | 0.9700 |
| C5—C6 | 1.376 (3) | C11—C11i | 1.511 (3) |
| C5—H5A | 0.9300 | C11—H11A | 0.9700 |
| C6—H6A | 0.9300 | C11—H11B | 0.9700 |
| C1—O1—C10 | 118.67 (12) | C7—C8—C9 | 125.81 (15) |
| O1—C1—C6 | 123.36 (14) | C7—C8—H8A | 117.1 |
| O1—C1—C2 | 115.47 (12) | C9—C8—H8A | 117.1 |
| C6—C1—C2 | 121.17 (15) | C8—C9—H9A | 109.5 |
| C3—C2—C1 | 117.23 (14) | C8—C9—H9B | 109.5 |
| C3—C2—C7 | 122.96 (14) | H9A—C9—H9B | 109.5 |
| C1—C2—C7 | 119.78 (12) | C8—C9—H9C | 109.5 |
| C4—C3—C2 | 121.55 (18) | H9A—C9—H9C | 109.5 |
| C4—C3—H3A | 119.2 | H9B—C9—H9C | 109.5 |
| C2—C3—H3A | 119.2 | O1—C10—C11 | 107.57 (13) |
| C5—C4—C3 | 120.05 (17) | O1—C10—H10A | 110.2 |
| C5—C4—H4A | 120.0 | C11—C10—H10A | 110.2 |
| C3—C4—H4A | 120.0 | O1—C10—H10B | 110.2 |
| C4—C5—C6 | 120.20 (18) | C11—C10—H10B | 110.2 |
| C4—C5—H5A | 119.9 | H10A—C10—H10B | 108.5 |
| C6—C5—H5A | 119.9 | C10—C11—C11i | 112.91 (17) |
| C5—C6—C1 | 119.78 (18) | C10—C11—H11A | 109.0 |
| C5—C6—H6A | 120.1 | C11i—C11—H11A | 109.0 |
| C1—C6—H6A | 120.1 | C10—C11—H11B | 109.0 |
| C8—C7—C2 | 127.62 (14) | C11i—C11—H11B | 109.0 |
| C8—C7—H7A | 116.2 | H11A—C11—H11B | 107.8 |
| C2—C7—H7A | 116.2 | ||
| C10—O1—C1—C6 | −5.9 (2) | C3—C4—C5—C6 | −0.7 (3) |
| C10—O1—C1—C2 | 174.45 (13) | C4—C5—C6—C1 | 1.1 (3) |
| O1—C1—C2—C3 | 179.89 (13) | O1—C1—C6—C5 | 179.48 (15) |
| C6—C1—C2—C3 | 0.3 (2) | C2—C1—C6—C5 | −0.9 (2) |
| O1—C1—C2—C7 | −1.52 (18) | C3—C2—C7—C8 | −12.1 (2) |
| C6—C1—C2—C7 | 178.86 (14) | C1—C2—C7—C8 | 169.40 (15) |
| C1—C2—C3—C4 | 0.2 (2) | C2—C7—C8—C9 | 178.78 (15) |
| C7—C2—C3—C4 | −178.36 (15) | C1—O1—C10—C11 | −175.35 (13) |
| C2—C3—C4—C5 | 0.0 (3) | O1—C10—C11—C11i | 66.7 (2) |
| Symmetry codes: (i) −x, −y, −z. |
We thank Professor Victor N. Khrustalev for fruitful discussions and help in this work.
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For giving the important operationalisation to cross-linked polymers reactions of copolymerisation of various monomers, multifunctional comonomers [1] are used. By applying this method, the hi-tech processes for the preparation of polymeric sorbents, photorezisting materials for microelectronics, the composites for the laser technics of a special purposes, fixation of metalcomplex of catalysts, etc were obtained (Crivello et al. 1994). In practice, for obtaining polymers of demanded functional properties, polymerical transformations are carried out. However, it is necessary to notice, that obtaining such cross-linked copolymers have some difficulties connected with high reactivity of cross-linking comonomers (for example, divinylbenzene), which is reflected in heterogeneity of their structure and other important physical and chemical properties. Therefore, to prepare multifunctional monomers, on the basis of alkenylphenols with two double bonds, is rather important. The molecule of the title compound, C22H26O2 (I), is generated by a crystallographic inversion centre at the midpoint of the central C—C bond. A fold of the molecule is due to the twist in the central butylene bridge [O1—C10—C11—C11A torsion angle of 66.7 (2)°] (Fig. 1). Crystal packing is dominated by van der Waals interactions (Fig. 2).