Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802020251/ww6051sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802020251/ww6051Isup2.hkl |
CCDC reference: 202329
Under the protection of N2, a mixture of anhydrous ethyl ether (30 ml), magnesium turnings (1.2 g) and magnesium powder (1.2 g) with a small amount of iodine was added slowly to a solution of 4-methoxybenzyl chloride (3.92 g, 0.025 mol) in anhydrous ethyl ether (20 ml). The mixture was warmed to initiate the reaction, and then the remaining 4-methoxybenzyl chloride was added at a rate to maintain a gentle reflux. The reaction mixture was stirred under reflux for an additional 5 h and then treated dropwise at room temperature with a solution of 3,5-dimethoxybenzaldehyde (4.2 g, 0.025 mol) in of dry ethyl ether (30 ml). The reaction mixture was heated at reflux for an additional 4 h and was then treated cautiously with dilute HCl. The organic layer was separated and the aqueous layer extracted with ethyl ether. The combined organic extract was washed with water (30 ml) and brine (30 ml). After drying over anhydrous MgSO4, the solvent was evaporated under reduced pressure, and the residue was subjected to column chromatography on silica gel (ethyl acetate/petroleum ether = 1:3). The last fraction provided the title compound (I); yield 28%, m.p. 409.5– 410.5 K. 1H NMR (400 MHz, CDCl3, p.p.m.): δ 1.64 (2H, broad), 2.90 (2H, m), 3.77 (15H, t), 4.79 (1H, m), 5.83 (1H, s), 6.34 (2H, d), 6.45 (2H, d), 6.53 (2H, d), 6.80 (1H, d), 6.32 (1H, d), 7.07 (2H, d). Single crystals suitable for X-ray analysis were obtained by slow evaporation of solution in ethanol.
Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997) and SHELXTL (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Fig. 1. View of the molecular structure of (I), shown with 50% probability displacement ellipsoids. | |
Fig. 2. A packing diagram of (I), viewed along c axis. |
C26H30O7 | F(000) = 968 |
Mr = 454.50 | Dx = 1.225 Mg m−3 |
Monoclinic, P21/c | Melting point = 409.5–410.5 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 12.382 (9) Å | Cell parameters from 996 reflections |
b = 23.700 (15) Å | θ = 2.6–22.2° |
c = 8.664 (6) Å | µ = 0.09 mm−1 |
β = 104.313 (12)° | T = 293 K |
V = 2464 (3) Å3 | Prism, colorless |
Z = 4 | 0.40 × 0.30 × 0.30 mm |
Bruker CCD area-detector diffractometer | 4346 independent reflections |
Radiation source: fine-focus sealed tube | 2601 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
ϕ and ω scans | θmax = 25.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −12→14 |
Tmin = 0.965, Tmax = 0.974 | k = −27→28 |
10041 measured reflections | l = −9→10 |
Refinement on F2 | H-atom parameters constrained |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.07P)2] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.050 | (Δ/σ)max = 0.003 |
wR(F2) = 0.138 | Δρmax = 0.18 e Å−3 |
S = 1.05 | Δρmin = −0.21 e Å−3 |
4346 reflections | Extinction correction: SHELXL97 |
305 parameters | Extinction coefficient: 0.026 (3) |
0 restraints |
C26H30O7 | V = 2464 (3) Å3 |
Mr = 454.50 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.382 (9) Å | µ = 0.09 mm−1 |
b = 23.700 (15) Å | T = 293 K |
c = 8.664 (6) Å | 0.40 × 0.30 × 0.30 mm |
β = 104.313 (12)° |
Bruker CCD area-detector diffractometer | 4346 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | 2601 reflections with I > 2σ(I) |
Tmin = 0.965, Tmax = 0.974 | Rint = 0.038 |
10041 measured reflections |
R[F2 > 2σ(F2)] = 0.050 | 0 restraints |
wR(F2) = 0.138 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.18 e Å−3 |
4346 reflections | Δρmin = −0.21 e Å−3 |
305 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 | ||
O1 | 0.13631 (15) | 0.22374 (7) | 0.1250 (2) | 0.0492 (5) | |
H1 | 0.1092 | 0.2261 | 0.2021 | 0.074* | |
O2 | 0.05239 (14) | 0.21564 (7) | 0.37502 (19) | 0.0488 (5) | |
H2 | 0.0713 | 0.2340 | 0.4576 | 0.073* | |
O3 | −0.38208 (16) | 0.21372 (9) | −0.1049 (2) | 0.0688 (6) | |
O4 | 0.48118 (17) | 0.07787 (10) | 0.0136 (2) | 0.0789 (7) | |
O5 | 0.46271 (16) | 0.12714 (10) | 0.5388 (2) | 0.0751 (6) | |
O6 | 0.12277 (15) | 0.04906 (8) | 0.7254 (2) | 0.0665 (6) | |
O7 | −0.27788 (16) | 0.04966 (10) | 0.5200 (3) | 0.0842 (7) | |
C1 | 0.2600 (2) | 0.14343 (10) | 0.1517 (3) | 0.0423 (6) | |
C2 | 0.3207 (2) | 0.11973 (11) | 0.0554 (3) | 0.0501 (7) | |
H2A | 0.2900 | 0.1169 | −0.0537 | 0.060* | |
C3 | 0.4279 (2) | 0.09991 (11) | 0.1211 (3) | 0.0521 (7) | |
C4 | 0.4740 (2) | 0.10325 (11) | 0.2824 (3) | 0.0539 (7) | |
H4 | 0.5459 | 0.0902 | 0.3261 | 0.065* | |
C5 | 0.4111 (2) | 0.12641 (12) | 0.3785 (3) | 0.0523 (7) | |
C6 | 0.3056 (2) | 0.14732 (11) | 0.3158 (3) | 0.0487 (7) | |
H6 | 0.2654 | 0.1638 | 0.3815 | 0.058* | |
C7 | 0.5934 (2) | 0.05944 (16) | 0.0700 (4) | 0.0910 (11) | |
H7A | 0.6388 | 0.0904 | 0.1197 | 0.137* | |
H7B | 0.6204 | 0.0458 | −0.0179 | 0.137* | |
H7C | 0.5967 | 0.0297 | 0.1461 | 0.137* | |
C8 | 0.4006 (3) | 0.14650 (19) | 0.6460 (4) | 0.0972 (13) | |
H8A | 0.3792 | 0.1851 | 0.6223 | 0.146* | |
H8B | 0.4455 | 0.1438 | 0.7532 | 0.146* | |
H8C | 0.3350 | 0.1237 | 0.6348 | 0.146* | |
C9 | 0.1437 (2) | 0.16530 (10) | 0.0837 (3) | 0.0436 (6) | |
H9 | 0.1288 | 0.1630 | −0.0326 | 0.052* | |
C10 | 0.0560 (2) | 0.12933 (10) | 0.1353 (3) | 0.0433 (6) | |
H10A | 0.0568 | 0.0917 | 0.0916 | 0.052* | |
H10B | 0.0763 | 0.1261 | 0.2505 | 0.052* | |
C11 | −0.06072 (19) | 0.15270 (10) | 0.0832 (3) | 0.0383 (6) | |
C12 | −0.1212 (2) | 0.14265 (11) | −0.0733 (3) | 0.0487 (7) | |
H12 | −0.0883 | 0.1216 | −0.1400 | 0.058* | |
C13 | −0.2270 (2) | 0.16257 (11) | −0.1319 (3) | 0.0499 (7) | |
H13 | −0.2653 | 0.1545 | −0.2362 | 0.060* | |
C14 | −0.2770 (2) | 0.19470 (11) | −0.0359 (3) | 0.0451 (6) | |
C15 | −0.2191 (2) | 0.20578 (10) | 0.1194 (3) | 0.0436 (6) | |
H15 | −0.2523 | 0.2277 | 0.1840 | 0.052* | |
C16 | −0.1122 (2) | 0.18461 (9) | 0.1805 (3) | 0.0368 (6) | |
C17 | −0.4397 (3) | 0.24400 (17) | −0.0078 (4) | 0.0962 (13) | |
H17A | −0.4454 | 0.2209 | 0.0810 | 0.144* | |
H17B | −0.5130 | 0.2536 | −0.0695 | 0.144* | |
H17C | −0.3995 | 0.2779 | 0.0306 | 0.144* | |
C18 | −0.0585 (2) | 0.19563 (10) | 0.3566 (3) | 0.0385 (6) | |
H18 | −0.1014 | 0.2254 | 0.3931 | 0.046* | |
C19 | −0.06277 (19) | 0.14303 (10) | 0.4562 (3) | 0.0357 (6) | |
C20 | 0.0313 (2) | 0.11843 (11) | 0.5499 (3) | 0.0435 (6) | |
H20 | 0.1007 | 0.1347 | 0.5569 | 0.052* | |
C21 | 0.0236 (2) | 0.06924 (10) | 0.6345 (3) | 0.0423 (6) | |
C22 | −0.0781 (2) | 0.04401 (10) | 0.6261 (3) | 0.0443 (6) | |
H22 | −0.0830 | 0.0105 | 0.6797 | 0.053* | |
C23 | −0.1721 (2) | 0.06995 (11) | 0.5358 (3) | 0.0479 (7) | |
C24 | −0.1657 (2) | 0.11900 (11) | 0.4515 (3) | 0.0453 (6) | |
H24 | −0.2305 | 0.1358 | 0.3917 | 0.054* | |
C25 | 0.1209 (3) | −0.00009 (13) | 0.8181 (4) | 0.0746 (10) | |
H25A | 0.0742 | 0.0063 | 0.8898 | 0.112* | |
H25B | 0.1952 | −0.0087 | 0.8781 | 0.112* | |
H25C | 0.0920 | −0.0312 | 0.7491 | 0.112* | |
C26 | −0.2938 (3) | 0.00098 (19) | 0.6032 (6) | 0.141 (2) | |
H26A | −0.2536 | −0.0299 | 0.5719 | 0.212* | |
H26B | −0.3718 | −0.0080 | 0.5792 | 0.212* | |
H26C | −0.2669 | 0.0074 | 0.7156 | 0.212* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0565 (12) | 0.0483 (11) | 0.0444 (11) | 0.0075 (9) | 0.0155 (9) | 0.0123 (8) |
O2 | 0.0560 (12) | 0.0530 (12) | 0.0371 (10) | −0.0149 (9) | 0.0109 (8) | −0.0123 (8) |
O3 | 0.0521 (13) | 0.0898 (15) | 0.0564 (12) | 0.0195 (11) | −0.0021 (10) | −0.0080 (11) |
O4 | 0.0526 (13) | 0.1078 (18) | 0.0768 (15) | 0.0248 (12) | 0.0174 (11) | −0.0080 (13) |
O5 | 0.0563 (13) | 0.1132 (18) | 0.0467 (13) | −0.0063 (12) | −0.0046 (10) | 0.0129 (12) |
O6 | 0.0486 (12) | 0.0740 (13) | 0.0675 (13) | 0.0111 (10) | −0.0035 (10) | 0.0223 (11) |
O7 | 0.0473 (13) | 0.0873 (16) | 0.1117 (18) | −0.0151 (11) | 0.0077 (12) | 0.0395 (14) |
C1 | 0.0424 (15) | 0.0470 (15) | 0.0364 (15) | 0.0025 (12) | 0.0075 (12) | 0.0062 (12) |
C2 | 0.0454 (17) | 0.0647 (18) | 0.0385 (15) | 0.0074 (13) | 0.0071 (12) | 0.0026 (13) |
C3 | 0.0435 (17) | 0.0582 (18) | 0.0554 (18) | 0.0032 (13) | 0.0134 (14) | 0.0020 (14) |
C4 | 0.0357 (16) | 0.0594 (18) | 0.063 (2) | −0.0001 (13) | 0.0054 (14) | 0.0121 (15) |
C5 | 0.0465 (17) | 0.0618 (18) | 0.0420 (16) | −0.0082 (14) | −0.0012 (13) | 0.0121 (14) |
C6 | 0.0499 (17) | 0.0563 (17) | 0.0401 (15) | 0.0040 (13) | 0.0115 (12) | 0.0045 (13) |
C7 | 0.048 (2) | 0.112 (3) | 0.113 (3) | 0.0186 (19) | 0.0198 (19) | −0.015 (2) |
C8 | 0.082 (3) | 0.164 (4) | 0.0388 (19) | −0.018 (3) | 0.0018 (17) | 0.002 (2) |
C9 | 0.0458 (15) | 0.0515 (17) | 0.0330 (14) | 0.0086 (12) | 0.0087 (11) | 0.0017 (12) |
C10 | 0.0473 (16) | 0.0425 (15) | 0.0390 (14) | 0.0046 (12) | 0.0088 (12) | −0.0056 (12) |
C11 | 0.0418 (15) | 0.0383 (14) | 0.0344 (14) | 0.0009 (11) | 0.0085 (11) | −0.0027 (11) |
C12 | 0.0531 (18) | 0.0550 (17) | 0.0382 (15) | 0.0012 (13) | 0.0117 (13) | −0.0125 (12) |
C13 | 0.0498 (17) | 0.0625 (18) | 0.0327 (14) | −0.0009 (14) | 0.0013 (12) | −0.0105 (13) |
C14 | 0.0421 (16) | 0.0511 (16) | 0.0390 (15) | 0.0038 (13) | 0.0045 (12) | 0.0009 (12) |
C15 | 0.0498 (16) | 0.0415 (15) | 0.0400 (15) | 0.0042 (12) | 0.0122 (12) | −0.0036 (12) |
C16 | 0.0448 (15) | 0.0334 (13) | 0.0307 (13) | −0.0007 (11) | 0.0068 (11) | −0.0011 (11) |
C17 | 0.071 (2) | 0.120 (3) | 0.089 (3) | 0.044 (2) | 0.003 (2) | −0.019 (2) |
C18 | 0.0431 (15) | 0.0388 (14) | 0.0328 (13) | 0.0007 (12) | 0.0082 (11) | −0.0053 (11) |
C19 | 0.0404 (15) | 0.0379 (14) | 0.0282 (12) | 0.0032 (11) | 0.0072 (10) | −0.0061 (10) |
C20 | 0.0404 (15) | 0.0489 (16) | 0.0409 (15) | −0.0031 (12) | 0.0092 (12) | −0.0021 (13) |
C21 | 0.0434 (16) | 0.0453 (16) | 0.0362 (14) | 0.0059 (12) | 0.0058 (11) | −0.0015 (12) |
C22 | 0.0548 (17) | 0.0397 (15) | 0.0389 (14) | 0.0023 (13) | 0.0123 (12) | 0.0010 (12) |
C23 | 0.0420 (16) | 0.0516 (17) | 0.0494 (16) | −0.0037 (13) | 0.0099 (13) | 0.0021 (13) |
C24 | 0.0404 (16) | 0.0497 (16) | 0.0438 (15) | 0.0031 (12) | 0.0065 (12) | 0.0046 (13) |
C25 | 0.079 (2) | 0.073 (2) | 0.067 (2) | 0.0289 (18) | 0.0093 (17) | 0.0249 (18) |
C26 | 0.077 (3) | 0.133 (4) | 0.201 (5) | −0.039 (3) | 0.011 (3) | 0.097 (4) |
O1—C9 | 1.439 (3) | C10—H10A | 0.9700 |
O1—H1 | 0.8200 | C10—H10B | 0.9700 |
O2—C18 | 1.424 (3) | C11—C16 | 1.398 (3) |
O2—H2 | 0.8200 | C11—C12 | 1.398 (3) |
O3—C14 | 1.367 (3) | C12—C13 | 1.367 (3) |
O3—C17 | 1.424 (4) | C12—H12 | 0.9300 |
O4—C3 | 1.370 (3) | C13—C14 | 1.382 (3) |
O4—C7 | 1.423 (3) | C13—H13 | 0.9300 |
O5—C5 | 1.378 (3) | C14—C15 | 1.384 (3) |
O5—C8 | 1.420 (4) | C15—C16 | 1.393 (3) |
O6—C21 | 1.371 (3) | C15—H15 | 0.9300 |
O6—C25 | 1.418 (3) | C16—C18 | 1.528 (3) |
O7—C23 | 1.370 (3) | C17—H17A | 0.9600 |
O7—C26 | 1.400 (4) | C17—H17B | 0.9600 |
C1—C2 | 1.373 (3) | C17—H17C | 0.9600 |
C1—C6 | 1.397 (3) | C18—C19 | 1.524 (3) |
C1—C9 | 1.507 (3) | C18—H18 | 0.9800 |
C2—C3 | 1.391 (4) | C19—C20 | 1.374 (3) |
C2—H2A | 0.9300 | C19—C24 | 1.388 (3) |
C3—C4 | 1.375 (4) | C20—C21 | 1.393 (3) |
C4—C5 | 1.387 (4) | C20—H20 | 0.9300 |
C4—H4 | 0.9300 | C21—C22 | 1.380 (3) |
C5—C6 | 1.377 (4) | C22—C23 | 1.376 (3) |
C6—H6 | 0.9300 | C22—H22 | 0.9300 |
C7—H7A | 0.9600 | C23—C24 | 1.386 (3) |
C7—H7B | 0.9600 | C24—H24 | 0.9300 |
C7—H7C | 0.9600 | C25—H25A | 0.9600 |
C8—H8A | 0.9600 | C25—H25B | 0.9600 |
C8—H8B | 0.9600 | C25—H25C | 0.9600 |
C8—H8C | 0.9600 | C26—H26A | 0.9600 |
C9—C10 | 1.532 (3) | C26—H26B | 0.9600 |
C9—H9 | 0.9800 | C26—H26C | 0.9600 |
C10—C11 | 1.509 (3) | ||
C9—O1—H1 | 109.5 | C12—C13—C14 | 119.8 (2) |
C18—O2—H2 | 109.5 | C12—C13—H13 | 120.1 |
C14—O3—C17 | 118.0 (2) | C14—C13—H13 | 120.1 |
C3—O4—C7 | 118.5 (2) | O3—C14—C13 | 115.9 (2) |
C5—O5—C8 | 118.1 (2) | O3—C14—C15 | 124.8 (2) |
C21—O6—C25 | 118.3 (2) | C13—C14—C15 | 119.3 (2) |
C23—O7—C26 | 119.4 (2) | C14—C15—C16 | 121.1 (2) |
C2—C1—C6 | 120.0 (2) | C14—C15—H15 | 119.5 |
C2—C1—C9 | 121.1 (2) | C16—C15—H15 | 119.5 |
C6—C1—C9 | 118.8 (2) | C15—C16—C11 | 119.9 (2) |
C1—C2—C3 | 120.0 (2) | C15—C16—C18 | 117.1 (2) |
C1—C2—H2A | 120.0 | C11—C16—C18 | 123.0 (2) |
C3—C2—H2A | 120.0 | O3—C17—H17A | 109.5 |
O4—C3—C4 | 124.3 (3) | O3—C17—H17B | 109.5 |
O4—C3—C2 | 115.0 (2) | H17A—C17—H17B | 109.5 |
C4—C3—C2 | 120.7 (3) | O3—C17—H17C | 109.5 |
C3—C4—C5 | 118.6 (3) | H17A—C17—H17C | 109.5 |
C3—C4—H4 | 120.7 | H17B—C17—H17C | 109.5 |
C5—C4—H4 | 120.7 | O2—C18—C19 | 112.09 (19) |
C6—C5—O5 | 123.5 (3) | O2—C18—C16 | 109.72 (19) |
C6—C5—C4 | 121.6 (2) | C19—C18—C16 | 110.99 (18) |
O5—C5—C4 | 114.9 (2) | O2—C18—H18 | 108.0 |
C5—C6—C1 | 118.9 (2) | C19—C18—H18 | 108.0 |
C5—C6—H6 | 120.5 | C16—C18—H18 | 108.0 |
C1—C6—H6 | 120.5 | C20—C19—C24 | 118.8 (2) |
O4—C7—H7A | 109.5 | C20—C19—C18 | 122.6 (2) |
O4—C7—H7B | 109.5 | C24—C19—C18 | 118.6 (2) |
H7A—C7—H7B | 109.5 | C19—C20—C21 | 120.5 (2) |
O4—C7—H7C | 109.5 | C19—C20—H20 | 119.8 |
H7A—C7—H7C | 109.5 | C21—C20—H20 | 119.8 |
H7B—C7—H7C | 109.5 | O6—C21—C22 | 123.8 (2) |
O5—C8—H8A | 109.5 | O6—C21—C20 | 115.2 (2) |
O5—C8—H8B | 109.5 | C22—C21—C20 | 121.0 (2) |
H8A—C8—H8B | 109.5 | C23—C22—C21 | 118.0 (2) |
O5—C8—H8C | 109.5 | C23—C22—H22 | 121.0 |
H8A—C8—H8C | 109.5 | C21—C22—H22 | 121.0 |
H8B—C8—H8C | 109.5 | O7—C23—C22 | 123.6 (2) |
O1—C9—C1 | 110.3 (2) | O7—C23—C24 | 114.8 (2) |
O1—C9—C10 | 111.71 (19) | C22—C23—C24 | 121.6 (2) |
C1—C9—C10 | 111.9 (2) | C23—C24—C19 | 120.0 (2) |
O1—C9—H9 | 107.6 | C23—C24—H24 | 120.0 |
C1—C9—H9 | 107.6 | C19—C24—H24 | 120.0 |
C10—C9—H9 | 107.6 | O6—C25—H25A | 109.5 |
C11—C10—C9 | 113.8 (2) | O6—C25—H25B | 109.5 |
C11—C10—H10A | 108.8 | H25A—C25—H25B | 109.5 |
C9—C10—H10A | 108.8 | O6—C25—H25C | 109.5 |
C11—C10—H10B | 108.8 | H25A—C25—H25C | 109.5 |
C9—C10—H10B | 108.8 | H25B—C25—H25C | 109.5 |
H10A—C10—H10B | 107.7 | O7—C26—H26A | 109.5 |
C16—C11—C12 | 117.5 (2) | O7—C26—H26B | 109.5 |
C16—C11—C10 | 124.3 (2) | H26A—C26—H26B | 109.5 |
C12—C11—C10 | 118.1 (2) | O7—C26—H26C | 109.5 |
C13—C12—C11 | 122.4 (2) | H26A—C26—H26C | 109.5 |
C13—C12—H12 | 118.8 | H26B—C26—H26C | 109.5 |
C11—C12—H12 | 118.8 | ||
C6—C1—C2—C3 | −0.4 (4) | C13—C14—C15—C16 | −0.6 (4) |
C9—C1—C2—C3 | 179.9 (2) | C14—C15—C16—C11 | 1.5 (4) |
C7—O4—C3—C4 | −3.0 (4) | C14—C15—C16—C18 | −175.7 (2) |
C7—O4—C3—C2 | 176.7 (3) | C12—C11—C16—C15 | −1.0 (3) |
C1—C2—C3—O4 | −179.1 (2) | C10—C11—C16—C15 | 178.0 (2) |
C1—C2—C3—C4 | 0.6 (4) | C12—C11—C16—C18 | 176.0 (2) |
O4—C3—C4—C5 | −179.8 (3) | C10—C11—C16—C18 | −5.0 (4) |
C2—C3—C4—C5 | 0.5 (4) | C15—C16—C18—O2 | −132.8 (2) |
C8—O5—C5—C6 | 5.0 (4) | C11—C16—C18—O2 | 50.1 (3) |
C8—O5—C5—C4 | −175.6 (3) | C15—C16—C18—C19 | 102.8 (2) |
C3—C4—C5—C6 | −1.8 (4) | C11—C16—C18—C19 | −74.3 (3) |
C3—C4—C5—O5 | 178.8 (2) | O2—C18—C19—C20 | −0.8 (3) |
O5—C5—C6—C1 | −178.7 (2) | C16—C18—C19—C20 | 122.2 (2) |
C4—C5—C6—C1 | 2.0 (4) | O2—C18—C19—C24 | 179.41 (19) |
C2—C1—C6—C5 | −0.9 (4) | C16—C18—C19—C24 | −57.5 (3) |
C9—C1—C6—C5 | 178.8 (2) | C24—C19—C20—C21 | 2.0 (3) |
C2—C1—C9—O1 | −123.5 (2) | C18—C19—C20—C21 | −177.8 (2) |
C6—C1—C9—O1 | 56.8 (3) | C25—O6—C21—C22 | −1.0 (4) |
C2—C1—C9—C10 | 111.5 (3) | C25—O6—C21—C20 | 178.4 (2) |
C6—C1—C9—C10 | −68.2 (3) | C19—C20—C21—O6 | −179.2 (2) |
O1—C9—C10—C11 | 50.2 (3) | C19—C20—C21—C22 | 0.2 (4) |
C1—C9—C10—C11 | 174.5 (2) | O6—C21—C22—C23 | 177.2 (2) |
C9—C10—C11—C16 | −98.3 (3) | C20—C21—C22—C23 | −2.2 (3) |
C9—C10—C11—C12 | 80.7 (3) | C26—O7—C23—C22 | 2.3 (5) |
C16—C11—C12—C13 | −0.3 (4) | C26—O7—C23—C24 | −178.6 (3) |
C10—C11—C12—C13 | −179.3 (2) | C21—C22—C23—O7 | −178.9 (2) |
C11—C12—C13—C14 | 1.1 (4) | C21—C22—C23—C24 | 2.0 (4) |
C17—O3—C14—C13 | 176.1 (3) | O7—C23—C24—C19 | −178.9 (2) |
C17—O3—C14—C15 | −4.4 (4) | C22—C23—C24—C19 | 0.2 (4) |
C12—C13—C14—O3 | 178.9 (2) | C20—C19—C24—C23 | −2.2 (3) |
C12—C13—C14—C15 | −0.6 (4) | C18—C19—C24—C23 | 177.5 (2) |
O3—C14—C15—C16 | 179.9 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2 | 0.82 | 1.82 | 2.631 (3) | 168 |
O2—H2···O1i | 0.82 | 1.78 | 2.593 (2) | 169 |
Symmetry code: (i) x, −y+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C26H30O7 |
Mr | 454.50 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 12.382 (9), 23.700 (15), 8.664 (6) |
β (°) | 104.313 (12) |
V (Å3) | 2464 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.40 × 0.30 × 0.30 |
Data collection | |
Diffractometer | Bruker CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 1997) |
Tmin, Tmax | 0.965, 0.974 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10041, 4346, 2601 |
Rint | 0.038 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.050, 0.138, 1.05 |
No. of reflections | 4346 |
No. of parameters | 305 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.18, −0.21 |
Computer programs: SMART (Bruker, 1997), SMART, SAINT (Bruker, 1997) and SHELXTL (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL.
C1—C9 | 1.507 (3) | C10—C11 | 1.509 (3) |
C9—C10 | 1.532 (3) | ||
C1—C9—C10—C11 | 174.5 (2) | C16—C18—C19—C20 | 122.2 (2) |
C9—C10—C11—C16 | −98.3 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2 | 0.82 | 1.82 | 2.631 (3) | 168 |
O2—H2···O1i | 0.82 | 1.78 | 2.593 (2) | 169 |
Symmetry code: (i) x, −y+1/2, z+1/2. |
Grignard reaction is one of the important methods of preparing stilbene derivatives (Campen et al., 1948). In this paper, a very interesting by-product, the title compound, (I), has been isolated from the Grignard reaction between one molecule of 4-methoxybenzylmagnesium chloride with two molecules of 3,5-dimethoxybenzaldehyde.
From the molecular structure illustrated in Fig. 1, the two new chiral centers, C9 and C18, adopt the same absolute configuration R (S). It seems that the formation of the second chiral center, C9, is controlled by the first one, C18. The two benzene rings, A and B, adopt anti conformations, as shown in Fig. 1, and the two hydroxy groups (O1H1 and O2H2) surrounded by the three benzene rings form an intermolecular hydrogen bond, viz. O1—H1···O2. As expected, Csp3—Csp3 hybridized bond length C9—C10 [1.532 (3) Å] is obviously longer than those of Csp2—Csp3 hybridized C1—C9 [1.507 (3) Å] and C10—C11 [1.509 (3) Å].
It was found that the five methoxy groups with varied stretching directions are almost coplanar with their attached benzene rings. The angle O4—C3—C4 [124.3 (3)°] is larger than that of O4—C3—C2 [115.0 (2)°]. It was assumed that this conformation will minimize the van der Waals interaction between the H atom on C4 and the C7 methyl group. The other four methoxy groups present the same structures. This kind of `open-mouthed' arrangement of methoxy groups were also found in other compounds (Zhang et al., 2001; Zheng et al., 2001). The angle between ring planes A and B is 11.4 (3)° and that between ring plane A and C is 85.2 (3)°. [Please define these planes] The torsion angles C6—C1—C9—O1 and C11—C16—C18—O2 are 56.8 (3) and 50.1 (3)°, respectively,while O2—C18—C19—C24 is −0.8 (3)°.