Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270102001816/bm1488sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270102001816/bm1488Isup2.hkl |
CCDC reference: 184491
Data collection: COLLECT (Nonius, 1999); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX (McArdle, 1995); software used to prepare material for publication: local program.
C22H24O3 | Dx = 1.311 Mg m−3 |
Mr = 336.41 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pca21 | Cell parameters from 24364 reflections |
a = 13.3194 (3) Å | θ = 3.1–27.4° |
b = 7.7311 (1) Å | µ = 0.09 mm−1 |
c = 16.5545 (3) Å | T = 150 K |
V = 1704.68 (5) Å3 | Rectangular prism, colourless |
Z = 4 | 0.34 × 0.23 × 0.13 mm |
F(000) = 720 |
Nonius KappaCCD area-detector diffractometer | 1989 independent reflections |
Radiation source: sealed tube | 1841 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.069 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.4°, θmin = 3.1° |
Please provide scans | h = −17→17 |
Absorption correction: multi-scan (Blessing, 1995) | k = −9→9 |
Tmin = 0.971, Tmax = 0.989 | l = −21→21 |
24364 measured reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.034 | w = 1/[σ2(Fo2) + (0.049P)2 + 0.241P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.084 | (Δ/σ)max = 0.001 |
S = 1.05 | Δρmax = 0.20 e Å−3 |
1989 reflections | Δρmin = −0.19 e Å−3 |
227 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
1 restraint | Extinction coefficient: 0.014 (3) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983) |
Secondary atom site location: difference Fourier map | Absolute structure parameter: not reliably determined |
Experimental. Detector set at 30 mm from sample with different 2theta offsets 1 degree phi exposures for chi=0 degree settings 1 degree omega exposures for chi=90 degree settings |
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. Structure solution was achieved by direct methods using SHELXS97 (Sheldrick, 1990), while least squares refinement used SHELXL97 (Sheldrick, 1997). No disorder was detected during refinement. All non-H atoms were refined anisotropically, while H atoms were placed in calculated positions and refined using a riding model. Fixed C—H distances were: C{aryl}-H = 0.95 Å, C{methyl}-H = 0.98 Å, C{secondary}-H = 0.99 Å, C(tertiary}-H = 1.00 Å. A Flack parameter of 0.8 (9) was refined from 1840 Friedel pairs, making it impossible to unambiguously determine the absolute structure of the compound. The Friedel opposites in the data were merged for the final cycles of least squares refinement. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.41397 (15) | 0.4043 (2) | 0.04869 (13) | 0.0250 (4) | |
C2 | 0.45879 (15) | 0.4401 (3) | 0.12234 (13) | 0.0266 (4) | |
H2 | 0.4280 | 0.5208 | 0.1578 | 0.032* | |
C3 | 0.54842 (14) | 0.3598 (3) | 0.14559 (13) | 0.0272 (4) | |
C4 | 0.59501 (14) | 0.2458 (3) | 0.09346 (15) | 0.0291 (4) | |
H4 | 0.6559 | 0.1905 | 0.1084 | 0.035* | |
C5 | 0.55121 (14) | 0.2131 (3) | 0.01858 (14) | 0.0280 (4) | |
H5 | 0.5838 | 0.1360 | −0.0176 | 0.034* | |
C6 | 0.46138 (14) | 0.2896 (2) | −0.00512 (12) | 0.0251 (4) | |
C7 | 0.31339 (14) | 0.4864 (3) | 0.02863 (14) | 0.0263 (4) | |
H7A | 0.3216 | 0.5545 | −0.0216 | 0.032* | |
H7B | 0.2966 | 0.5688 | 0.0723 | 0.032* | |
C8 | 0.22287 (14) | 0.3639 (2) | 0.01712 (13) | 0.0245 (4) | |
H8 | 0.1632 | 0.4422 | 0.0140 | 0.029* | |
C9 | 0.20033 (15) | 0.2417 (3) | 0.08864 (13) | 0.0265 (4) | |
H9A | 0.1796 | 0.3146 | 0.1349 | 0.032* | |
H9B | 0.1415 | 0.1705 | 0.0735 | 0.032* | |
C10 | 0.41463 (14) | 0.2398 (3) | −0.08456 (14) | 0.0273 (4) | |
H10A | 0.4623 | 0.1645 | −0.1140 | 0.033* | |
H10B | 0.4054 | 0.3460 | −0.1171 | 0.033* | |
C11 | 0.31233 (14) | 0.1451 (3) | −0.07911 (12) | 0.0239 (4) | |
H11 | 0.3007 | 0.0964 | −0.1343 | 0.029* | |
C12 | 0.31238 (14) | −0.0123 (3) | −0.02228 (13) | 0.0248 (4) | |
H12A | 0.2456 | −0.0676 | −0.0271 | 0.030* | |
H12B | 0.3618 | −0.0957 | −0.0442 | 0.030* | |
C13 | 0.28116 (14) | 0.1197 (3) | 0.11861 (13) | 0.0251 (4) | |
C14 | 0.30152 (17) | 0.1160 (3) | 0.20134 (14) | 0.0310 (5) | |
H14 | 0.2661 | 0.1923 | 0.2361 | 0.037* | |
C15 | 0.37200 (18) | 0.0040 (3) | 0.23438 (14) | 0.0344 (5) | |
H15 | 0.3832 | 0.0020 | 0.2910 | 0.041* | |
C16 | 0.42576 (17) | −0.1044 (3) | 0.18395 (15) | 0.0329 (5) | |
H16 | 0.4754 | −0.1797 | 0.2055 | 0.039* | |
C17 | 0.40660 (15) | −0.1022 (3) | 0.10173 (13) | 0.0279 (4) | |
H17 | 0.4440 | −0.1768 | 0.0675 | 0.033* | |
C18 | 0.33419 (14) | 0.0060 (2) | 0.06749 (12) | 0.0236 (4) | |
C19 | 0.22499 (13) | 0.2699 (3) | −0.06473 (13) | 0.0245 (4) | |
O20 | 0.22574 (10) | 0.3934 (2) | −0.12874 (9) | 0.0301 (3) | |
C21 | 0.12361 (16) | 0.4390 (3) | −0.14584 (15) | 0.0380 (5) | |
H21A | 0.1114 | 0.4410 | −0.2048 | 0.046* | |
H21B | 0.1072 | 0.5540 | −0.1232 | 0.046* | |
C22 | 0.06099 (15) | 0.2976 (3) | −0.10523 (15) | 0.0349 (5) | |
H22A | 0.0208 | 0.3459 | −0.0603 | 0.042* | |
H22B | 0.0151 | 0.2423 | −0.1446 | 0.042* | |
O23 | 0.13333 (9) | 0.17619 (19) | −0.07582 (9) | 0.0284 (3) | |
O24 | 0.58278 (11) | 0.4026 (2) | 0.22178 (10) | 0.0357 (4) | |
C25 | 0.66780 (18) | 0.3078 (4) | 0.25037 (17) | 0.0436 (6) | |
H25A | 0.6540 | 0.1835 | 0.2467 | 0.065* | |
H25B | 0.6812 | 0.3388 | 0.3067 | 0.065* | |
H25C | 0.7266 | 0.3359 | 0.2173 | 0.065* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0250 (9) | 0.0193 (9) | 0.0306 (10) | −0.0026 (7) | 0.0019 (8) | 0.0031 (8) |
C2 | 0.0272 (9) | 0.0200 (9) | 0.0326 (11) | −0.0022 (8) | 0.0043 (8) | −0.0006 (8) |
C3 | 0.0238 (9) | 0.0258 (10) | 0.0320 (10) | −0.0063 (7) | −0.0015 (8) | 0.0045 (9) |
C4 | 0.0206 (9) | 0.0260 (10) | 0.0408 (12) | −0.0018 (7) | 0.0011 (9) | 0.0031 (9) |
C5 | 0.0202 (8) | 0.0251 (9) | 0.0386 (11) | −0.0019 (7) | 0.0046 (8) | −0.0034 (9) |
C6 | 0.0213 (8) | 0.0231 (10) | 0.0310 (11) | −0.0049 (7) | 0.0039 (7) | 0.0015 (8) |
C7 | 0.0260 (9) | 0.0214 (9) | 0.0315 (10) | 0.0014 (7) | 0.0015 (8) | −0.0020 (8) |
C8 | 0.0225 (9) | 0.0229 (9) | 0.0281 (10) | 0.0027 (7) | 0.0026 (8) | −0.0014 (8) |
C9 | 0.0277 (9) | 0.0263 (10) | 0.0256 (9) | 0.0024 (8) | 0.0064 (8) | −0.0034 (8) |
C10 | 0.0233 (9) | 0.0295 (10) | 0.0292 (10) | 0.0004 (7) | 0.0054 (8) | −0.0021 (9) |
C11 | 0.0230 (8) | 0.0257 (9) | 0.0231 (9) | 0.0018 (7) | 0.0029 (7) | −0.0055 (8) |
C12 | 0.0223 (8) | 0.0224 (9) | 0.0297 (10) | 0.0009 (7) | 0.0025 (8) | −0.0053 (8) |
C13 | 0.0263 (9) | 0.0205 (9) | 0.0286 (10) | −0.0045 (7) | 0.0031 (8) | −0.0004 (8) |
C14 | 0.0390 (11) | 0.0266 (10) | 0.0274 (10) | −0.0049 (8) | 0.0044 (9) | −0.0037 (9) |
C15 | 0.0445 (12) | 0.0309 (11) | 0.0278 (11) | −0.0079 (9) | −0.0039 (10) | 0.0014 (9) |
C16 | 0.0332 (11) | 0.0277 (11) | 0.0377 (12) | −0.0028 (9) | −0.0065 (9) | 0.0050 (9) |
C17 | 0.0275 (9) | 0.0235 (10) | 0.0327 (12) | −0.0023 (8) | 0.0016 (8) | −0.0013 (8) |
C18 | 0.0232 (8) | 0.0193 (9) | 0.0282 (10) | −0.0052 (7) | 0.0012 (7) | −0.0008 (8) |
C19 | 0.0208 (9) | 0.0254 (9) | 0.0272 (10) | −0.0002 (7) | 0.0013 (7) | 0.0001 (8) |
O20 | 0.0296 (8) | 0.0329 (8) | 0.0279 (8) | 0.0028 (6) | 0.0001 (6) | 0.0058 (6) |
C21 | 0.0339 (11) | 0.0455 (13) | 0.0347 (12) | 0.0124 (10) | 0.0002 (9) | 0.0056 (11) |
C22 | 0.0239 (9) | 0.0415 (12) | 0.0392 (12) | 0.0055 (9) | −0.0028 (9) | −0.0024 (10) |
O23 | 0.0211 (6) | 0.0301 (7) | 0.0341 (8) | −0.0003 (6) | −0.0020 (6) | −0.0036 (7) |
O24 | 0.0304 (7) | 0.0398 (9) | 0.0370 (9) | 0.0026 (6) | −0.0049 (7) | −0.0035 (7) |
C25 | 0.0341 (12) | 0.0550 (15) | 0.0418 (13) | 0.0032 (11) | −0.0108 (10) | −0.0018 (12) |
C1—C2 | 1.385 (3) | C12—C18 | 1.521 (3) |
C1—C6 | 1.407 (3) | C12—H12A | 0.9900 |
C1—C7 | 1.519 (3) | C12—H12B | 0.9900 |
C2—C3 | 1.399 (3) | C13—C14 | 1.397 (3) |
C2—H2 | 0.9500 | C13—C18 | 1.410 (3) |
C3—C4 | 1.381 (3) | C14—C15 | 1.389 (3) |
C3—O24 | 1.382 (3) | C14—H14 | 0.9500 |
C4—C5 | 1.393 (3) | C15—C16 | 1.383 (3) |
C4—H4 | 0.9500 | C15—H15 | 0.9500 |
C5—C6 | 1.391 (3) | C16—C17 | 1.385 (3) |
C5—H5 | 0.9500 | C16—H16 | 0.9500 |
C6—C10 | 1.505 (3) | C17—C18 | 1.397 (3) |
C7—C8 | 1.545 (3) | C17—H17 | 0.9500 |
C7—H7A | 0.9900 | C19—O20 | 1.427 (2) |
C7—H7B | 0.9900 | C19—O23 | 1.431 (2) |
C8—C19 | 1.538 (3) | O20—C21 | 1.433 (3) |
C8—C9 | 1.544 (3) | C21—C22 | 1.530 (3) |
C8—H8 | 1.0000 | C21—H21A | 0.9900 |
C9—C13 | 1.515 (3) | C21—H21B | 0.9900 |
C9—H9A | 0.9900 | C22—O23 | 1.431 (3) |
C9—H9B | 0.9900 | C22—H22A | 0.9900 |
C10—C11 | 1.550 (3) | C22—H22B | 0.9900 |
C10—H10A | 0.9900 | O24—C25 | 1.430 (3) |
C10—H10B | 0.9900 | C25—H25A | 0.9800 |
C11—C19 | 1.530 (3) | C25—H25B | 0.9800 |
C11—C12 | 1.538 (3) | C25—H25C | 0.9800 |
C11—H11 | 1.0000 | ||
C2—C1—C6 | 119.31 (19) | C11—C12—H12A | 106.9 |
C2—C1—C7 | 119.29 (18) | C18—C12—H12B | 106.9 |
C6—C1—C7 | 121.38 (19) | C11—C12—H12B | 106.9 |
C1—C2—C3 | 121.42 (19) | H12A—C12—H12B | 106.7 |
C1—C2—H2 | 119.3 | C14—C13—C18 | 118.58 (19) |
C3—C2—H2 | 119.3 | C14—C13—C9 | 118.17 (19) |
C4—C3—O24 | 125.06 (19) | C18—C13—C9 | 123.21 (19) |
C4—C3—C2 | 119.6 (2) | C15—C14—C13 | 122.0 (2) |
O24—C3—C2 | 115.29 (19) | C15—C14—H14 | 119.0 |
C3—C4—C5 | 118.92 (18) | C13—C14—H14 | 119.0 |
C3—C4—H4 | 120.5 | C16—C15—C14 | 119.3 (2) |
C5—C4—H4 | 120.5 | C16—C15—H15 | 120.3 |
C6—C5—C4 | 122.29 (19) | C14—C15—H15 | 120.3 |
C6—C5—H5 | 118.9 | C15—C16—C17 | 119.4 (2) |
C4—C5—H5 | 118.9 | C15—C16—H16 | 120.3 |
C5—C6—C1 | 118.39 (19) | C17—C16—H16 | 120.3 |
C5—C6—C10 | 119.57 (19) | C16—C17—C18 | 122.2 (2) |
C1—C6—C10 | 121.93 (18) | C16—C17—H17 | 118.9 |
C1—C7—C8 | 117.35 (16) | C18—C17—H17 | 118.9 |
C1—C7—H7A | 108.0 | C17—C18—C13 | 118.41 (19) |
C8—C7—H7A | 108.0 | C17—C18—C12 | 118.19 (18) |
C1—C7—H7B | 108.0 | C13—C18—C12 | 123.30 (18) |
C8—C7—H7B | 108.0 | O20—C19—O23 | 104.45 (15) |
H7A—C7—H7B | 107.2 | O20—C19—C11 | 107.55 (15) |
C19—C8—C9 | 112.96 (15) | O23—C19—C11 | 108.02 (15) |
C19—C8—C7 | 112.58 (16) | O20—C19—C8 | 109.76 (15) |
C9—C8—C7 | 115.60 (17) | O23—C19—C8 | 109.66 (15) |
C19—C8—H8 | 104.8 | C11—C19—C8 | 116.69 (16) |
C9—C8—H8 | 104.8 | C19—O20—C21 | 107.73 (16) |
C7—C8—H8 | 104.8 | O20—C21—C22 | 104.78 (17) |
C13—C9—C8 | 119.59 (16) | O20—C21—H21A | 110.8 |
C13—C9—H9A | 107.4 | C22—C21—H21A | 110.8 |
C8—C9—H9A | 107.4 | O20—C21—H21B | 110.8 |
C13—C9—H9B | 107.4 | C22—C21—H21B | 110.8 |
C8—C9—H9B | 107.4 | H21A—C21—H21B | 108.9 |
H9A—C9—H9B | 107.0 | O23—C22—C21 | 104.53 (16) |
C6—C10—C11 | 115.71 (17) | O23—C22—H22A | 110.8 |
C6—C10—H10A | 108.4 | C21—C22—H22A | 110.8 |
C11—C10—H10A | 108.4 | O23—C22—H22B | 110.8 |
C6—C10—H10B | 108.4 | C21—C22—H22B | 110.8 |
C11—C10—H10B | 108.4 | H22A—C22—H22B | 108.9 |
H10A—C10—H10B | 107.4 | C22—O23—C19 | 106.62 (15) |
C19—C11—C12 | 113.84 (16) | C3—O24—C25 | 116.20 (18) |
C19—C11—C10 | 112.30 (16) | O24—C25—H25A | 109.5 |
C12—C11—C10 | 114.15 (16) | O24—C25—H25B | 109.5 |
C19—C11—H11 | 105.1 | H25A—C25—H25B | 109.5 |
C12—C11—H11 | 105.1 | O24—C25—H25C | 109.5 |
C10—C11—H11 | 105.1 | H25A—C25—H25C | 109.5 |
C18—C12—C11 | 121.59 (17) | H25B—C25—H25C | 109.5 |
C18—C12—H12A | 106.9 |