supplementary materials
[3,5-Bis(benzyloxy)phenyl]methanol
In the title compound, C21H20O3, the two terminal phenyl rings are each approximately perpendicular to the central benzene ring, making dihedral angles of 84.40 (16) and 75.12 (15)°. The H atom of the hydroxy group is disordered over two positions with equal occupancies. The molecules are linked by O-H
O hydrogen bonds, forming a chain along the a axis.
Benzylbromide (10.0 g, 58 mmol), 3,5-dihydroxybenzyl alcohol (4.10 g, 129 mmol),
18-crown-6-ether (1.54 g, 5.8 mmol) and potassium carbonate (16 g, 578.6 mmol)
were suspended in 500 ml of 2-butanone under nitrogen atmosphere. The mixture
was heated under reflux for 48 h. Upon completion of the reaction, the solvent
was evaporated and the water and dichloromethanewere added to the residue.
Conventional workup and purification by silica-gel column chromatography
(eluent: dichloromethane) yielded 5.6 g of the title compound
(60%) as a white needle (Hawker & Fréchet, 1990). Single
crystals suitable for X-ray study were grown by diffusion method
[dichloromethane/n-hexane (1:4 v/v)] at room temperature.
H atoms bound to carbon were refined using a riding model, with
C—H = 0.93 Å and Uiso(H) = 1.2Ueq (C) for aromatic atoms,
and
C—H = 0.97 Å and
Uiso(H) = 1.2Ueq (C) for methylene atoms.
The H atom of the OH group was found to be disordered over two positions
with approximately equal occupancies from a difference Fourier map.
The positions were then constrained,
with Uiso(H) = 1.2Ueq(O), and with equal occupancies.
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
[3,5-Bis(benzyloxy)phenyl]methanol
top
Crystal data top
| C21H20O3 | Z = 2 |
| Mr = 320.37 | F(000) = 340 |
| Triclinic, P1 | Dx = 1.249 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 4.8555 (6) Å | Cell parameters from 1252 reflections |
| b = 12.2442 (18) Å | θ = 2.5–23.9° |
| c = 15.017 (2) Å | µ = 0.08 mm−1 |
| α = 74.049 (1)° | T = 298 K |
| β = 83.293 (1)° | Needle, colorless |
| γ = 89.733 (2)° | 0.46 × 0.16 × 0.15 mm |
| V = 852.2 (2) Å3 | |
Data collection top
Bruker APEXII CCD area-detector
diffractometer | 2909 independent reflections |
| Radiation source: fine-focus sealed tube | 1563 reflections with I > 2σ(I) |
| graphite | Rint = 0.035 |
| φ and ω scans | θmax = 25.0°, θmin = 1.4° |
Absorption correction: multi-scan
(SADABS; Bruker, 2001) | h = −5→5 |
| Tmin = 0.963, Tmax = 0.988 | k = −14→13 |
| 4355 measured reflections | l = −17→17 |
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)] = 0.057 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.168 | H-atom parameters constrained |
| S = 0.99 | w = 1/[σ2(Fo2) + (0.0808P)2]
where P = (Fo2 + 2Fc2)/3 |
| 2909 reflections | (Δ/σ)max = 0.001 |
| 217 parameters | Δρmax = 0.37 e Å−3 |
| 0 restraints | Δρmin = −0.21 e Å−3 |
Crystal data top
| C21H20O3 | γ = 89.733 (2)° |
| Mr = 320.37 | V = 852.2 (2) Å3 |
| Triclinic, P1 | Z = 2 |
| a = 4.8555 (6) Å | Mo Kα radiation |
| b = 12.2442 (18) Å | µ = 0.08 mm−1 |
| c = 15.017 (2) Å | T = 298 K |
| α = 74.049 (1)° | 0.46 × 0.16 × 0.15 mm |
| β = 83.293 (1)° | |
Data collection top
Bruker APEXII CCD area-detector
diffractometer | 2909 independent reflections |
Absorption correction: multi-scan
(SADABS; Bruker, 2001) | 1563 reflections with I > 2σ(I) |
| Tmin = 0.963, Tmax = 0.988 | Rint = 0.035 |
| 4355 measured reflections | θmax = 25.0° |
Refinement top
| R[F2 > 2σ(F2)] = 0.057 | H-atom parameters constrained |
| wR(F2) = 0.168 | Δρmax = 0.37 e Å−3 |
| S = 0.99 | Δρmin = −0.21 e Å−3 |
| 2909 reflections | Absolute structure: ? |
| 217 parameters | Flack parameter: ? |
| 0 restraints | Rogers 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| | x | y | z | Uiso*/Ueq | Occ. (<1) |
| O1 | 0.7476 (4) | 0.54725 (14) | 0.18038 (12) | 0.0568 (6) | |
| O2 | 0.7536 (4) | 0.14526 (14) | 0.29783 (13) | 0.0635 (6) | |
| O3 | 1.2666 (5) | 0.48874 (17) | 0.45678 (15) | 0.0789 (7) | |
| H3 | 1.3738 | 0.4982 | 0.4970 | 0.095* | 0.50 |
| H3' | 1.1026 | 0.4958 | 0.4828 | 0.095* | 0.50 |
| C1 | 0.8253 (5) | 0.4491 (2) | 0.24052 (17) | 0.0426 (6) | |
| C2 | 0.7487 (5) | 0.34076 (19) | 0.23990 (17) | 0.0453 (7) | |
| H2A | 0.6341 | 0.3299 | 0.1974 | 0.054* | |
| C3 | 0.8453 (6) | 0.2488 (2) | 0.30348 (18) | 0.0464 (7) | |
| C4 | 1.0120 (6) | 0.2635 (2) | 0.36729 (18) | 0.0480 (7) | |
| H4A | 1.0747 | 0.2007 | 0.4098 | 0.058* | |
| C5 | 1.0871 (5) | 0.3729 (2) | 0.36817 (17) | 0.0425 (6) | |
| C6 | 0.9927 (5) | 0.4648 (2) | 0.30581 (17) | 0.0438 (7) | |
| H6A | 1.0402 | 0.5379 | 0.3069 | 0.053* | |
| C7 | 0.5903 (6) | 0.5371 (2) | 0.10822 (18) | 0.0533 (7) | |
| H7A | 0.4095 | 0.5024 | 0.1351 | 0.064* | |
| H7B | 0.6854 | 0.4897 | 0.0729 | 0.064* | |
| C8 | 0.5585 (6) | 0.6536 (2) | 0.04585 (18) | 0.0496 (7) | |
| C9 | 0.7312 (7) | 0.6937 (3) | −0.0356 (2) | 0.0754 (10) | |
| H9A | 0.8676 | 0.6473 | −0.0528 | 0.090* | |
| C10 | 0.7059 (10) | 0.8012 (3) | −0.0920 (3) | 0.0962 (13) | |
| H10A | 0.8263 | 0.8274 | −0.1467 | 0.115* | |
| C11 | 0.5067 (10) | 0.8696 (3) | −0.0687 (3) | 0.0908 (12) | |
| H11A | 0.4883 | 0.9422 | −0.1076 | 0.109* | |
| C12 | 0.3331 (9) | 0.8312 (3) | 0.0124 (3) | 0.1023 (13) | |
| H12A | 0.1982 | 0.8781 | 0.0297 | 0.123* | |
| C13 | 0.3587 (8) | 0.7224 (3) | 0.0687 (2) | 0.0794 (10) | |
| H13A | 0.2372 | 0.6959 | 0.1232 | 0.095* | |
| C14 | 0.8719 (7) | 0.0468 (2) | 0.3518 (2) | 0.0680 (9) | |
| H14A | 0.8331 | 0.0422 | 0.4176 | 0.082* | |
| H14B | 1.0716 | 0.0501 | 0.3354 | 0.082* | |
| C15 | 0.7497 (7) | −0.0552 (2) | 0.3328 (2) | 0.0557 (8) | |
| C16 | 0.8521 (8) | −0.0914 (3) | 0.2569 (2) | 0.0772 (10) | |
| H16A | 0.9985 | −0.0510 | 0.2158 | 0.093* | |
| C17 | 0.7416 (8) | −0.1859 (3) | 0.2410 (3) | 0.0869 (11) | |
| H17A | 0.8147 | −0.2090 | 0.1893 | 0.104* | |
| C18 | 0.5285 (9) | −0.2461 (3) | 0.2992 (3) | 0.0790 (11) | |
| H18A | 0.4561 | −0.3106 | 0.2880 | 0.095* | |
| C19 | 0.4214 (8) | −0.2119 (3) | 0.3736 (3) | 0.0840 (11) | |
| H19A | 0.2732 | −0.2526 | 0.4136 | 0.101* | |
| C20 | 0.5308 (7) | −0.1165 (3) | 0.3910 (2) | 0.0724 (9) | |
| H20A | 0.4552 | −0.0937 | 0.4427 | 0.087* | |
| C21 | 1.2750 (6) | 0.3847 (2) | 0.43799 (19) | 0.0533 (7) | |
| H21C | 1.2243 | 0.3258 | 0.4958 | 0.064* | |
| H21A | 1.4641 | 0.3721 | 0.4148 | 0.064* | |
Atomic displacement parameters (Å2) top| | U11 | U22 | U33 | U12 | U13 | U23 |
| O1 | 0.0814 (15) | 0.0381 (10) | 0.0525 (11) | −0.0110 (9) | −0.0322 (10) | −0.0052 (9) |
| O2 | 0.0863 (16) | 0.0319 (10) | 0.0791 (14) | 0.0001 (9) | −0.0387 (12) | −0.0149 (9) |
| O3 | 0.0913 (17) | 0.0735 (14) | 0.0969 (17) | 0.0106 (12) | −0.0500 (14) | −0.0495 (13) |
| C1 | 0.0504 (17) | 0.0370 (14) | 0.0399 (14) | −0.0060 (12) | −0.0073 (12) | −0.0090 (12) |
| C2 | 0.0548 (18) | 0.0405 (15) | 0.0447 (15) | −0.0049 (12) | −0.0162 (13) | −0.0141 (12) |
| C3 | 0.0544 (18) | 0.0364 (14) | 0.0529 (16) | −0.0019 (12) | −0.0106 (14) | −0.0179 (13) |
| C4 | 0.0553 (18) | 0.0407 (15) | 0.0521 (16) | 0.0023 (12) | −0.0168 (14) | −0.0156 (13) |
| C5 | 0.0382 (15) | 0.0501 (16) | 0.0421 (14) | −0.0022 (12) | −0.0080 (12) | −0.0166 (13) |
| C6 | 0.0480 (17) | 0.0412 (15) | 0.0451 (14) | −0.0094 (12) | −0.0073 (13) | −0.0162 (12) |
| C7 | 0.067 (2) | 0.0495 (17) | 0.0465 (15) | −0.0089 (14) | −0.0208 (14) | −0.0128 (13) |
| C8 | 0.0575 (19) | 0.0477 (16) | 0.0469 (16) | −0.0056 (14) | −0.0173 (14) | −0.0139 (13) |
| C9 | 0.090 (3) | 0.064 (2) | 0.064 (2) | −0.0044 (18) | 0.0077 (19) | −0.0125 (18) |
| C10 | 0.131 (4) | 0.074 (3) | 0.065 (2) | −0.018 (2) | 0.002 (2) | 0.005 (2) |
| C11 | 0.114 (3) | 0.060 (2) | 0.087 (3) | −0.006 (2) | −0.039 (3) | 0.010 (2) |
| C12 | 0.109 (3) | 0.073 (3) | 0.112 (3) | 0.023 (2) | −0.015 (3) | −0.002 (2) |
| C13 | 0.082 (3) | 0.073 (2) | 0.070 (2) | 0.014 (2) | −0.0027 (18) | 0.0004 (18) |
| C14 | 0.097 (3) | 0.0410 (16) | 0.073 (2) | 0.0056 (16) | −0.0391 (18) | −0.0153 (15) |
| C15 | 0.072 (2) | 0.0330 (15) | 0.0616 (19) | 0.0019 (14) | −0.0210 (16) | −0.0064 (14) |
| C16 | 0.088 (3) | 0.059 (2) | 0.086 (2) | −0.0220 (18) | 0.009 (2) | −0.0278 (18) |
| C17 | 0.093 (3) | 0.072 (2) | 0.109 (3) | −0.006 (2) | −0.003 (2) | −0.050 (2) |
| C18 | 0.092 (3) | 0.0474 (19) | 0.102 (3) | −0.0107 (19) | −0.037 (2) | −0.019 (2) |
| C19 | 0.084 (3) | 0.069 (2) | 0.088 (3) | −0.028 (2) | −0.020 (2) | 0.001 (2) |
| C20 | 0.081 (3) | 0.070 (2) | 0.065 (2) | 0.0024 (19) | −0.0113 (19) | −0.0148 (18) |
| C21 | 0.0524 (18) | 0.0574 (17) | 0.0596 (18) | 0.0020 (14) | −0.0189 (14) | −0.0267 (15) |
Geometric parameters (Å, °) top
| O1—C1 | 1.371 (3) | C10—C11 | 1.354 (5) |
| O1—C7 | 1.429 (3) | C10—H10A | 0.9300 |
| O2—C3 | 1.374 (3) | C11—C12 | 1.365 (5) |
| O2—C14 | 1.416 (3) | C11—H11A | 0.9300 |
| O3—C21 | 1.378 (3) | C12—C13 | 1.381 (5) |
| O3—H3 | 0.8727 | C12—H12A | 0.9300 |
| O3—H3' | 0.8599 | C13—H13A | 0.9300 |
| C1—C2 | 1.382 (3) | C14—C15 | 1.496 (4) |
| C1—C6 | 1.396 (3) | C14—H14A | 0.9700 |
| C2—C3 | 1.381 (3) | C14—H14B | 0.9700 |
| C2—H2A | 0.9300 | C15—C16 | 1.372 (4) |
| C3—C4 | 1.372 (3) | C15—C20 | 1.374 (4) |
| C4—C5 | 1.394 (3) | C16—C17 | 1.369 (4) |
| C4—H4A | 0.9300 | C16—H16A | 0.9300 |
| C5—C6 | 1.367 (3) | C17—C18 | 1.349 (5) |
| C5—C21 | 1.503 (3) | C17—H17A | 0.9300 |
| C6—H6A | 0.9300 | C18—C19 | 1.347 (5) |
| C7—C8 | 1.494 (4) | C18—H18A | 0.9300 |
| C7—H7A | 0.9700 | C19—C20 | 1.387 (4) |
| C7—H7B | 0.9700 | C19—H19A | 0.9300 |
| C8—C13 | 1.358 (4) | C20—H20A | 0.9300 |
| C8—C9 | 1.369 (4) | C21—H21C | 0.9700 |
| C9—C10 | 1.370 (5) | C21—H21A | 0.9700 |
| C9—H9A | 0.9300 | | |
| | | |
| C1—O1—C7 | 117.82 (18) | C10—C11—H11A | 120.3 |
| C3—O2—C14 | 117.6 (2) | C12—C11—H11A | 120.3 |
| C21—O3—H3 | 116.4 | C11—C12—C13 | 119.7 (4) |
| C21—O3—H3' | 107.9 | C11—C12—H12A | 120.1 |
| H3—O3—H3' | 103.4 | C13—C12—H12A | 120.1 |
| O1—C1—C2 | 124.7 (2) | C8—C13—C12 | 121.0 (3) |
| O1—C1—C6 | 115.0 (2) | C8—C13—H13A | 119.5 |
| C2—C1—C6 | 120.3 (2) | C12—C13—H13A | 119.5 |
| C3—C2—C1 | 118.9 (2) | O2—C14—C15 | 108.6 (2) |
| C3—C2—H2A | 120.6 | O2—C14—H14A | 110.0 |
| C1—C2—H2A | 120.6 | C15—C14—H14A | 110.0 |
| C4—C3—O2 | 124.6 (2) | O2—C14—H14B | 110.0 |
| C4—C3—C2 | 121.2 (2) | C15—C14—H14B | 110.0 |
| O2—C3—C2 | 114.1 (2) | H14A—C14—H14B | 108.4 |
| C3—C4—C5 | 119.7 (2) | C16—C15—C20 | 117.6 (3) |
| C3—C4—H4A | 120.1 | C16—C15—C14 | 121.4 (3) |
| C5—C4—H4A | 120.1 | C20—C15—C14 | 121.0 (3) |
| C6—C5—C4 | 119.8 (2) | C17—C16—C15 | 120.9 (3) |
| C6—C5—C21 | 122.4 (2) | C17—C16—H16A | 119.5 |
| C4—C5—C21 | 117.8 (2) | C15—C16—H16A | 119.5 |
| C5—C6—C1 | 120.1 (2) | C18—C17—C16 | 121.0 (4) |
| C5—C6—H6A | 119.9 | C18—C17—H17A | 119.5 |
| C1—C6—H6A | 119.9 | C16—C17—H17A | 119.5 |
| O1—C7—C8 | 108.02 (19) | C19—C18—C17 | 119.4 (3) |
| O1—C7—H7A | 110.1 | C19—C18—H18A | 120.3 |
| C8—C7—H7A | 110.1 | C17—C18—H18A | 120.3 |
| O1—C7—H7B | 110.1 | C18—C19—C20 | 120.4 (3) |
| C8—C7—H7B | 110.1 | C18—C19—H19A | 119.8 |
| H7A—C7—H7B | 108.4 | C20—C19—H19A | 119.8 |
| C13—C8—C9 | 118.4 (3) | C15—C20—C19 | 120.6 (3) |
| C13—C8—C7 | 120.9 (3) | C15—C20—H20A | 119.7 |
| C9—C8—C7 | 120.8 (3) | C19—C20—H20A | 119.7 |
| C8—C9—C10 | 120.9 (3) | O3—C21—C5 | 114.2 (2) |
| C8—C9—H9A | 119.6 | O3—C21—H21C | 108.7 |
| C10—C9—H9A | 119.6 | C5—C21—H21C | 108.7 |
| C11—C10—C9 | 120.5 (4) | O3—C21—H21A | 108.7 |
| C11—C10—H10A | 119.8 | C5—C21—H21A | 108.7 |
| C9—C10—H10A | 119.8 | H21C—C21—H21A | 107.6 |
| C10—C11—C12 | 119.5 (4) | | |
| | | |
| C7—O1—C1—C2 | −4.0 (4) | C7—C8—C9—C10 | −178.8 (3) |
| C7—O1—C1—C6 | 176.2 (2) | C8—C9—C10—C11 | −0.7 (6) |
| O1—C1—C2—C3 | 178.9 (2) | C9—C10—C11—C12 | 0.9 (6) |
| C6—C1—C2—C3 | −1.3 (4) | C10—C11—C12—C13 | −1.3 (6) |
| C14—O2—C3—C4 | −10.0 (4) | C9—C8—C13—C12 | −1.3 (5) |
| C14—O2—C3—C2 | 171.7 (2) | C7—C8—C13—C12 | 178.3 (3) |
| C1—C2—C3—C4 | 0.7 (4) | C11—C12—C13—C8 | 1.6 (6) |
| C1—C2—C3—O2 | 179.1 (2) | C3—O2—C14—C15 | −178.2 (2) |
| O2—C3—C4—C5 | −178.4 (2) | O2—C14—C15—C16 | 83.4 (4) |
| C2—C3—C4—C5 | −0.3 (4) | O2—C14—C15—C20 | −96.8 (3) |
| C3—C4—C5—C6 | 0.4 (4) | C20—C15—C16—C17 | −0.9 (5) |
| C3—C4—C5—C21 | −178.7 (2) | C14—C15—C16—C17 | 178.9 (3) |
| C4—C5—C6—C1 | −1.0 (4) | C15—C16—C17—C18 | 0.2 (6) |
| C21—C5—C6—C1 | 178.1 (2) | C16—C17—C18—C19 | 0.6 (6) |
| O1—C1—C6—C5 | −178.8 (2) | C17—C18—C19—C20 | −0.7 (5) |
| C2—C1—C6—C5 | 1.5 (4) | C16—C15—C20—C19 | 0.8 (5) |
| C1—O1—C7—C8 | −173.7 (2) | C14—C15—C20—C19 | −179.0 (3) |
| O1—C7—C8—C13 | −82.1 (3) | C18—C19—C20—C15 | 0.0 (5) |
| O1—C7—C8—C9 | 97.5 (3) | C6—C5—C21—O3 | 21.5 (4) |
| C13—C8—C9—C10 | 0.9 (5) | C4—C5—C21—O3 | −159.4 (2) |
Hydrogen-bond geometry (Å, °) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| O3—H3···O3i | 0.87 | 1.98 | 2.791 (4) | 155 |
| O3—H3'···O3ii | 0.86 | 1.95 | 2.805 (5) | 179 |
| Symmetry codes: (i) −x+3, −y+1, −z+1; (ii) −x+2, −y+1, −z+1. |
Table 1
Hydrogen-bond geometry (Å, °) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| O3—H3···O3i | 0.87 | 1.98 | 2.791 (4) | 155 |
| O3—H3'···O3ii | 0.86 | 1.95 | 2.805 (5) | 179 |
| Symmetry codes: (i) −x+3, −y+1, −z+1; (ii) −x+2, −y+1, −z+1. |
This work was supported by Shandong Province (2007BS02016) and the Key Subject
Research Foundation of Shandong Province (XTD 0705).
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Xiao, Z.-P., Fang, R.-Q., Shi, L., Ding, H., Chen, X. & Zhu, H.-L. (2007). Can. J. Chem. 85, 951–957.
![[Figure 1]](./is2400fig1thm.gif)
Dendrimers are three-dimensional hyperbranched macromolecules that provide well defined nanoscopic objects at the single molecular level. Recent studies on dendritic macromolecules have extended the scope of research from synthesis to applications for catalysts, photoactive and electronic materials, medicinal and biomedical materials, and other functional materials. As a part of our structural investigations on dendritic macromolecules, the single-crystal X-ray diffraction study on the title compound was carried out.
In the title compound, the bond lengths and angles are within the normal ranges. Each unit cell of the title compound contains two molecules like other analogues reported before (Pan et al., 2005; Rheiner & Seebach, 1999; Xiao et al., 2007). It is worth noting that the dihedral angles between the central benzene ring and the two peripheral phenyl rings are 84.40 (16) and 75.12 (15)°. Probably because of the effects of substitution of the central benzene ring, the dihedral angels of the title compound are different from ones reported (Xiao et al., 2007). The O—CH2 bonds lie in the plane of the central phenyl ring and adopt a syn, anti conformation (Pan et al., 2005). The crystal structure is stabilized by intermolecular hydrogen bonds.