Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806048136/wn2081sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806048136/wn2081VIsup2.hkl |
CCDC reference: 630502
Data collection: APEX2, (Bruker 2004); cell refinement: APEX2; data reduction: SAINT, (Bruker 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker 2004); software used to prepare material for publication: SHELXTL.
C29H26O | F(000) = 832 |
Mr = 390.50 | Dx = 1.174 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 11.5290 (8) Å | Cell parameters from 2527 reflections |
b = 11.3445 (8) Å | θ = 2.5–21.8° |
c = 16.9415 (12) Å | µ = 0.07 mm−1 |
β = 94.124 (1)° | T = 291 K |
V = 2210.1 (3) Å3 | Block, colourless |
Z = 4 | 0.35 × 0.18 × 0.09 mm |
Bruker ApexII CCD area-detector diffractometer | 5053 independent reflections |
Radiation source: fine-focus sealed tube | 3024 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
φ and ω scans | θmax = 27.5°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Sheldrick,1996) | h = −14→14 |
Tmin = 0.976, Tmax = 0.994 | k = −14→14 |
13103 measured reflections | l = −12→21 |
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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.146 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.065P)2 + 0.2364P] where P = (Fo2 + 2Fc2)/3 |
5053 reflections | (Δ/σ)max < 0.001 |
275 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
Experimental. IR spectra were obtained on a Shimadzu-IR 435 spectrometer. 1H-NMR spectra were recorded on a Bruker AC–P200 spectrometer with TMS as the internal standard. Elemental analysis was performed on a Yanaco MT-3 instrument. Melting points were determined with a model Yanaco MP-500 apparatus and uncorrected. |
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 | −0.05573 (9) | 0.52133 (10) | 0.22760 (7) | 0.0499 (3) | |
C1 | 0.02356 (14) | 0.70141 (14) | 0.28369 (10) | 0.0471 (4) | |
C2 | 0.00158 (15) | 0.81414 (15) | 0.31856 (10) | 0.0501 (4) | |
C3 | 0.09189 (18) | 0.88901 (16) | 0.34917 (12) | 0.0638 (5) | |
H3 | 0.1690 | 0.8664 | 0.3461 | 0.077* | |
C4 | 0.0671 (2) | 0.99450 (19) | 0.38335 (14) | 0.0786 (6) | |
H4 | 0.1277 | 1.0429 | 0.4029 | 0.094* | |
C5 | −0.0481 (2) | 1.03080 (19) | 0.38940 (13) | 0.0786 (6) | |
H5 | −0.0636 | 1.1029 | 0.4125 | 0.094* | |
C6 | −0.13680 (19) | 0.96044 (17) | 0.36139 (12) | 0.0664 (5) | |
H6 | −0.2131 | 0.9844 | 0.3660 | 0.080* | |
C7 | −0.11483 (15) | 0.85058 (15) | 0.32505 (10) | 0.0526 (4) | |
C8 | −0.20620 (16) | 0.77609 (17) | 0.29728 (11) | 0.0599 (5) | |
H8 | −0.2827 | 0.8009 | 0.3001 | 0.072* | |
C9 | −0.18454 (15) | 0.66785 (17) | 0.26615 (11) | 0.0571 (5) | |
H9 | −0.2459 | 0.6190 | 0.2486 | 0.069* | |
C10 | −0.07002 (14) | 0.63104 (15) | 0.26090 (10) | 0.0469 (4) | |
C11 | 0.13810 (14) | 0.65912 (16) | 0.26738 (11) | 0.0548 (5) | |
H11 | 0.2014 | 0.7102 | 0.2712 | 0.066* | |
C12 | 0.15246 (15) | 0.54795 (16) | 0.24703 (11) | 0.0547 (5) | |
H12 | 0.2246 | 0.5232 | 0.2320 | 0.066* | |
C13 | 0.05385 (13) | 0.46006 (15) | 0.24772 (10) | 0.0463 (4) | |
C14 | 0.05931 (13) | 0.36723 (15) | 0.18275 (10) | 0.0473 (4) | |
C15 | 0.08758 (15) | 0.40152 (17) | 0.10790 (11) | 0.0568 (5) | |
H15 | 0.1049 | 0.4803 | 0.0990 | 0.068* | |
C16 | 0.09075 (16) | 0.32194 (19) | 0.04607 (10) | 0.0601 (5) | |
C17 | 0.06515 (15) | 0.20493 (18) | 0.06114 (11) | 0.0603 (5) | |
H17 | 0.0681 | 0.1502 | 0.0205 | 0.072* | |
C18 | 0.03534 (15) | 0.16678 (17) | 0.13457 (11) | 0.0553 (5) | |
C19 | 0.03291 (14) | 0.24949 (16) | 0.19521 (10) | 0.0508 (4) | |
H19 | 0.0132 | 0.2254 | 0.2450 | 0.061* | |
C20 | 0.1227 (2) | 0.3622 (2) | −0.03457 (12) | 0.0925 (8) | |
H20A | 0.2052 | 0.3558 | −0.0377 | 0.139* | |
H20B | 0.0994 | 0.4428 | −0.0427 | 0.139* | |
H20C | 0.0837 | 0.3137 | −0.0746 | 0.139* | |
C21 | 0.0056 (2) | 0.03991 (19) | 0.14847 (14) | 0.0859 (7) | |
H21A | −0.0731 | 0.0251 | 0.1286 | 0.129* | |
H21B | 0.0136 | 0.0235 | 0.2042 | 0.129* | |
H21C | 0.0573 | −0.0099 | 0.1216 | 0.129* | |
C22 | 0.05351 (14) | 0.40690 (14) | 0.33044 (9) | 0.0439 (4) | |
C23 | 0.15580 (15) | 0.35773 (16) | 0.36443 (10) | 0.0527 (4) | |
H23 | 0.2215 | 0.3562 | 0.3357 | 0.063* | |
C24 | 0.16198 (16) | 0.31105 (17) | 0.44007 (11) | 0.0593 (5) | |
C25 | 0.06333 (17) | 0.31587 (16) | 0.48215 (11) | 0.0602 (5) | |
H25 | 0.0669 | 0.2861 | 0.5334 | 0.072* | |
C26 | −0.03954 (16) | 0.36308 (15) | 0.45067 (10) | 0.0520 (4) | |
C27 | −0.04380 (14) | 0.40774 (14) | 0.37397 (10) | 0.0478 (4) | |
H27 | −0.1132 | 0.4387 | 0.3515 | 0.057* | |
C28 | −0.14498 (18) | 0.36910 (19) | 0.49831 (13) | 0.0733 (6) | |
H28A | −0.1582 | 0.2933 | 0.5212 | 0.110* | |
H28B | −0.2117 | 0.3913 | 0.4644 | 0.110* | |
H28C | −0.1321 | 0.4265 | 0.5397 | 0.110* | |
C29 | 0.2750 (2) | 0.2597 (2) | 0.47629 (15) | 0.0917 (7) | |
H29A | 0.3097 | 0.3137 | 0.5147 | 0.138* | |
H29B | 0.3272 | 0.2466 | 0.4355 | 0.138* | |
H29C | 0.2595 | 0.1862 | 0.5016 | 0.138* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0460 (6) | 0.0500 (7) | 0.0535 (7) | 0.0046 (5) | 0.0024 (5) | −0.0049 (6) |
C1 | 0.0486 (9) | 0.0466 (10) | 0.0460 (9) | −0.0020 (7) | 0.0041 (8) | 0.0073 (8) |
C2 | 0.0592 (10) | 0.0445 (10) | 0.0467 (10) | −0.0009 (8) | 0.0050 (8) | 0.0103 (8) |
C3 | 0.0706 (12) | 0.0522 (12) | 0.0686 (13) | −0.0117 (9) | 0.0046 (10) | 0.0054 (10) |
C4 | 0.0965 (17) | 0.0574 (13) | 0.0816 (16) | −0.0184 (12) | 0.0034 (13) | −0.0055 (11) |
C5 | 0.1078 (18) | 0.0524 (13) | 0.0753 (15) | −0.0008 (12) | 0.0057 (13) | −0.0086 (11) |
C6 | 0.0858 (14) | 0.0528 (12) | 0.0610 (12) | 0.0136 (10) | 0.0082 (11) | 0.0021 (10) |
C7 | 0.0631 (11) | 0.0469 (10) | 0.0476 (10) | 0.0054 (8) | 0.0027 (9) | 0.0062 (8) |
C8 | 0.0508 (10) | 0.0636 (12) | 0.0649 (12) | 0.0143 (9) | 0.0023 (9) | −0.0026 (10) |
C9 | 0.0468 (10) | 0.0617 (12) | 0.0619 (12) | 0.0009 (8) | −0.0023 (8) | −0.0068 (9) |
C10 | 0.0484 (9) | 0.0485 (10) | 0.0443 (9) | 0.0057 (7) | 0.0061 (7) | 0.0031 (8) |
C11 | 0.0472 (10) | 0.0544 (11) | 0.0639 (12) | −0.0046 (8) | 0.0106 (8) | 0.0067 (9) |
C12 | 0.0464 (10) | 0.0585 (12) | 0.0605 (12) | 0.0008 (8) | 0.0129 (8) | 0.0037 (9) |
C13 | 0.0408 (9) | 0.0502 (10) | 0.0483 (10) | 0.0070 (7) | 0.0055 (7) | −0.0006 (8) |
C14 | 0.0434 (9) | 0.0555 (11) | 0.0436 (9) | 0.0079 (7) | 0.0063 (7) | 0.0014 (8) |
C15 | 0.0579 (11) | 0.0612 (12) | 0.0526 (11) | 0.0125 (8) | 0.0127 (9) | 0.0100 (9) |
C16 | 0.0576 (11) | 0.0799 (14) | 0.0435 (10) | 0.0212 (10) | 0.0086 (8) | 0.0035 (10) |
C17 | 0.0594 (11) | 0.0766 (14) | 0.0446 (10) | 0.0181 (10) | 0.0015 (9) | −0.0133 (10) |
C18 | 0.0577 (10) | 0.0599 (11) | 0.0481 (10) | 0.0066 (8) | 0.0017 (8) | −0.0077 (9) |
C19 | 0.0537 (10) | 0.0579 (11) | 0.0412 (9) | 0.0035 (8) | 0.0063 (8) | −0.0009 (8) |
C20 | 0.1180 (19) | 0.111 (2) | 0.0521 (12) | 0.0354 (15) | 0.0294 (13) | 0.0159 (13) |
C21 | 0.1142 (19) | 0.0673 (15) | 0.0762 (15) | −0.0059 (13) | 0.0060 (14) | −0.0164 (12) |
C22 | 0.0473 (9) | 0.0424 (9) | 0.0422 (9) | −0.0013 (7) | 0.0045 (7) | −0.0065 (7) |
C23 | 0.0501 (10) | 0.0587 (11) | 0.0492 (10) | 0.0039 (8) | 0.0036 (8) | −0.0071 (9) |
C24 | 0.0652 (12) | 0.0565 (11) | 0.0549 (11) | 0.0018 (9) | −0.0060 (9) | −0.0014 (9) |
C25 | 0.0778 (13) | 0.0564 (11) | 0.0460 (10) | −0.0079 (10) | 0.0016 (10) | 0.0030 (9) |
C26 | 0.0629 (11) | 0.0433 (9) | 0.0509 (10) | −0.0118 (8) | 0.0125 (9) | −0.0056 (8) |
C27 | 0.0484 (9) | 0.0453 (9) | 0.0502 (10) | −0.0022 (7) | 0.0062 (8) | −0.0042 (8) |
C28 | 0.0821 (14) | 0.0736 (14) | 0.0678 (13) | −0.0191 (11) | 0.0306 (11) | −0.0039 (11) |
C29 | 0.0828 (15) | 0.1089 (19) | 0.0803 (16) | 0.0183 (14) | −0.0169 (13) | 0.0139 (14) |
O1—C10 | 1.381 (2) | C16—C17 | 1.388 (3) |
O1—C13 | 1.4607 (19) | C16—C20 | 1.511 (3) |
C1—C10 | 1.375 (2) | C17—C18 | 1.384 (3) |
C1—C2 | 1.439 (2) | C17—H17 | 0.9300 |
C1—C11 | 1.450 (2) | C18—C19 | 1.393 (2) |
C2—C3 | 1.413 (2) | C18—C21 | 1.502 (3) |
C2—C7 | 1.416 (2) | C19—H19 | 0.9300 |
C3—C4 | 1.369 (3) | C20—H20A | 0.9600 |
C3—H3 | 0.9300 | C20—H20B | 0.9600 |
C4—C5 | 1.401 (3) | C20—H20C | 0.9600 |
C4—H4 | 0.9300 | C21—H21A | 0.9600 |
C5—C6 | 1.356 (3) | C21—H21B | 0.9600 |
C5—H5 | 0.9300 | C21—H21C | 0.9600 |
C6—C7 | 1.421 (3) | C22—C27 | 1.386 (2) |
C6—H6 | 0.9300 | C22—C23 | 1.391 (2) |
C7—C8 | 1.405 (3) | C23—C24 | 1.384 (2) |
C8—C9 | 1.366 (2) | C23—H23 | 0.9300 |
C8—H8 | 0.9300 | C24—C25 | 1.386 (3) |
C9—C10 | 1.394 (2) | C24—C29 | 1.516 (3) |
C9—H9 | 0.9300 | C25—C26 | 1.374 (3) |
C11—C12 | 1.321 (2) | C25—H25 | 0.9300 |
C11—H11 | 0.9300 | C26—C27 | 1.392 (2) |
C12—C13 | 1.513 (2) | C26—C28 | 1.508 (2) |
C12—H12 | 0.9300 | C27—H27 | 0.9300 |
C13—C22 | 1.526 (2) | C28—H28A | 0.9600 |
C13—C14 | 1.528 (2) | C28—H28B | 0.9600 |
C14—C15 | 1.387 (2) | C28—H28C | 0.9600 |
C14—C19 | 1.389 (2) | C29—H29A | 0.9600 |
C15—C16 | 1.385 (3) | C29—H29B | 0.9600 |
C15—H15 | 0.9300 | C29—H29C | 0.9600 |
C10—O1—C13 | 117.39 (12) | C18—C17—C16 | 122.32 (17) |
C10—C1—C2 | 118.27 (15) | C18—C17—H17 | 118.8 |
C10—C1—C11 | 117.48 (15) | C16—C17—H17 | 118.8 |
C2—C1—C11 | 124.19 (15) | C17—C18—C19 | 118.15 (18) |
C3—C2—C7 | 118.26 (17) | C17—C18—C21 | 120.99 (18) |
C3—C2—C1 | 122.55 (16) | C19—C18—C21 | 120.86 (18) |
C7—C2—C1 | 119.16 (15) | C14—C19—C18 | 121.28 (16) |
C4—C3—C2 | 120.7 (2) | C14—C19—H19 | 119.4 |
C4—C3—H3 | 119.7 | C18—C19—H19 | 119.4 |
C2—C3—H3 | 119.7 | C16—C20—H20A | 109.5 |
C3—C4—C5 | 121.1 (2) | C16—C20—H20B | 109.5 |
C3—C4—H4 | 119.5 | H20A—C20—H20B | 109.5 |
C5—C4—H4 | 119.5 | C16—C20—H20C | 109.5 |
C6—C5—C4 | 119.8 (2) | H20A—C20—H20C | 109.5 |
C6—C5—H5 | 120.1 | H20B—C20—H20C | 109.5 |
C4—C5—H5 | 120.1 | C18—C21—H21A | 109.5 |
C5—C6—C7 | 121.0 (2) | C18—C21—H21B | 109.5 |
C5—C6—H6 | 119.5 | H21A—C21—H21B | 109.5 |
C7—C6—H6 | 119.5 | C18—C21—H21C | 109.5 |
C8—C7—C2 | 119.36 (16) | H21A—C21—H21C | 109.5 |
C8—C7—C6 | 121.33 (17) | H21B—C21—H21C | 109.5 |
C2—C7—C6 | 119.29 (17) | C27—C22—C23 | 118.49 (15) |
C9—C8—C7 | 121.08 (17) | C27—C22—C13 | 122.79 (14) |
C9—C8—H8 | 119.5 | C23—C22—C13 | 118.71 (14) |
C7—C8—H8 | 119.5 | C24—C23—C22 | 121.49 (16) |
C8—C9—C10 | 119.61 (17) | C24—C23—H23 | 119.3 |
C8—C9—H9 | 120.2 | C22—C23—H23 | 119.3 |
C10—C9—H9 | 120.2 | C23—C24—C25 | 118.15 (17) |
C1—C10—O1 | 121.58 (14) | C23—C24—C29 | 120.50 (18) |
C1—C10—C9 | 122.41 (16) | C25—C24—C29 | 121.33 (18) |
O1—C10—C9 | 115.94 (15) | C26—C25—C24 | 122.22 (17) |
C12—C11—C1 | 119.90 (16) | C26—C25—H25 | 118.9 |
C12—C11—H11 | 120.1 | C24—C25—H25 | 118.9 |
C1—C11—H11 | 120.1 | C25—C26—C27 | 118.41 (16) |
C11—C12—C13 | 121.26 (15) | C25—C26—C28 | 121.10 (17) |
C11—C12—H12 | 119.4 | C27—C26—C28 | 120.49 (17) |
C13—C12—H12 | 119.4 | C22—C27—C26 | 121.23 (16) |
O1—C13—C12 | 108.81 (14) | C22—C27—H27 | 119.4 |
O1—C13—C22 | 110.06 (12) | C26—C27—H27 | 119.4 |
C12—C13—C22 | 108.61 (14) | C26—C28—H28A | 109.5 |
O1—C13—C14 | 103.87 (12) | C26—C28—H28B | 109.5 |
C12—C13—C14 | 112.26 (13) | H28A—C28—H28B | 109.5 |
C22—C13—C14 | 113.09 (14) | C26—C28—H28C | 109.5 |
C15—C14—C19 | 118.48 (16) | H28A—C28—H28C | 109.5 |
C15—C14—C13 | 119.32 (16) | H28B—C28—H28C | 109.5 |
C19—C14—C13 | 122.16 (15) | C24—C29—H29A | 109.5 |
C16—C15—C14 | 121.95 (18) | C24—C29—H29B | 109.5 |
C16—C15—H15 | 119.0 | H29A—C29—H29B | 109.5 |
C14—C15—H15 | 119.0 | C24—C29—H29C | 109.5 |
C15—C16—C17 | 117.82 (17) | H29A—C29—H29C | 109.5 |
C15—C16—C20 | 120.5 (2) | H29B—C29—H29C | 109.5 |
C17—C16—C20 | 121.64 (19) | ||
C10—C1—C2—C3 | 175.23 (16) | C12—C13—C14—C15 | −41.6 (2) |
C11—C1—C2—C3 | −7.9 (3) | C22—C13—C14—C15 | −164.93 (14) |
C10—C1—C2—C7 | −2.7 (2) | O1—C13—C14—C19 | −101.94 (17) |
C11—C1—C2—C7 | 174.23 (16) | C12—C13—C14—C19 | 140.68 (16) |
C7—C2—C3—C4 | −0.7 (3) | C22—C13—C14—C19 | 17.4 (2) |
C1—C2—C3—C4 | −178.63 (18) | C19—C14—C15—C16 | −0.4 (2) |
C2—C3—C4—C5 | 0.4 (3) | C13—C14—C15—C16 | −178.19 (15) |
C3—C4—C5—C6 | 0.3 (3) | C14—C15—C16—C17 | −0.3 (3) |
C4—C5—C6—C7 | −0.7 (3) | C14—C15—C16—C20 | −179.60 (17) |
C3—C2—C7—C8 | −178.05 (16) | C15—C16—C17—C18 | 1.0 (3) |
C1—C2—C7—C8 | −0.1 (2) | C20—C16—C17—C18 | −179.74 (18) |
C3—C2—C7—C6 | 0.3 (2) | C16—C17—C18—C19 | −0.9 (3) |
C1—C2—C7—C6 | 178.32 (15) | C16—C17—C18—C21 | 178.66 (18) |
C5—C6—C7—C8 | 178.72 (19) | C15—C14—C19—C18 | 0.5 (2) |
C5—C6—C7—C2 | 0.4 (3) | C13—C14—C19—C18 | 178.23 (15) |
C2—C7—C8—C9 | 1.8 (3) | C17—C18—C19—C14 | 0.1 (3) |
C6—C7—C8—C9 | −176.53 (17) | C21—C18—C19—C14 | −179.44 (18) |
C7—C8—C9—C10 | −0.8 (3) | O1—C13—C22—C27 | 6.6 (2) |
C2—C1—C10—O1 | −179.47 (14) | C12—C13—C22—C27 | 125.63 (16) |
C11—C1—C10—O1 | 3.4 (2) | C14—C13—C22—C27 | −109.06 (17) |
C2—C1—C10—C9 | 3.8 (3) | O1—C13—C22—C23 | −171.95 (14) |
C11—C1—C10—C9 | −173.28 (16) | C12—C13—C22—C23 | −52.9 (2) |
C13—O1—C10—C1 | 26.3 (2) | C14—C13—C22—C23 | 72.38 (19) |
C13—O1—C10—C9 | −156.81 (15) | C27—C22—C23—C24 | −0.4 (3) |
C8—C9—C10—C1 | −2.1 (3) | C13—C22—C23—C24 | 178.21 (16) |
C8—C9—C10—O1 | −179.03 (15) | C22—C23—C24—C25 | −0.9 (3) |
C10—C1—C11—C12 | −13.8 (3) | C22—C23—C24—C29 | −179.05 (18) |
C2—C1—C11—C12 | 169.33 (17) | C23—C24—C25—C26 | 1.2 (3) |
C1—C11—C12—C13 | −5.8 (3) | C29—C24—C25—C26 | 179.38 (19) |
C10—O1—C13—C12 | −41.72 (18) | C24—C25—C26—C27 | −0.2 (3) |
C10—O1—C13—C22 | 77.18 (17) | C24—C25—C26—C28 | −178.93 (17) |
C10—O1—C13—C14 | −161.47 (13) | C23—C22—C27—C26 | 1.4 (2) |
C11—C12—C13—O1 | 32.4 (2) | C13—C22—C27—C26 | −177.12 (15) |
C11—C12—C13—C22 | −87.4 (2) | C25—C26—C27—C22 | −1.1 (2) |
C11—C12—C13—C14 | 146.79 (17) | C28—C26—C27—C22 | 177.57 (15) |
O1—C13—C14—C15 | 75.78 (17) |