Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806007872/om2006sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806007872/om2006Isup2.hkl |
CCDC reference: 605146
Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL and PLATON.
C24H22O2 | Dx = 1.219 Mg m−3 |
Mr = 342.42 | Melting point: 412 K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 4698 reflections |
a = 7.5637 (5) Å | θ = 1.9–26.4° |
b = 11.5604 (7) Å | µ = 0.08 mm−1 |
c = 21.3353 (13) Å | T = 295 K |
V = 1865.5 (2) Å3 | Prism, colorless |
Z = 4 | 0.38 × 0.20 × 0.14 mm |
F(000) = 728 |
Bruker SMART 1K CCD area-detector diffractometer | 2214 independent reflections |
Radiation source: fine-focus sealed tube | 1719 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
ω scans | θmax = 26.4°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | h = −9→9 |
Tmin = 0.878, Tmax = 0.989 | k = −14→13 |
10849 measured reflections | l = −26→22 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.039 | H-atom parameters constrained |
wR(F2) = 0.097 | w = 1/[σ2(Fo2) + (0.0523P)2 + 0.1176P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
2214 reflections | Δρmax = 0.13 e Å−3 |
238 parameters | Δρmin = −0.11 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.018 (2) |
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. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 7.4356 (0.0012) x + 2.0995 (0.0088) y - 0.5259 (0.0101) z = 1.1865 (0.0025) * 0.0046 (0.0018) C1 * 0.0154 (0.0019) C2 * 0.0040 (0.0019) C3 * -0.0120 (0.0022) C4 * -0.0097 (0.0024) C5 * 0.0023 (0.0023) C6 * 0.0145 (0.0022) C7 * 0.0034 (0.0024) C8 * -0.0085 (0.0021) C9 * -0.0139 (0.0018) C10 - 0.0480 (0.0026) O1 - 0.2914 (0.0040) C11 - 0.5643 (0.0052) C12 - 0.0392 (0.0033) C13 Rms deviation of fitted atoms = 0.0100 - 2.8374 (0.0031) x + 0.9911 (0.0083) y + 19.6924 (0.0043) z = 1.4447 (0.0015) Angle to previous plane (with approximate e.s.d.) = 67.92 (0.04) * -0.0109 (0.0016) C13 * -0.0183 (0.0018) C14 * 0.0085 (0.0018) C15 * 0.0181 (0.0021) C16 * -0.0044 (0.0022) C17 * -0.0059 (0.0020) C18 * -0.0097 (0.0020) C19 * 0.0036 (0.0020) C20 * 0.0155 (0.0020) C21 * 0.0035 (0.0018) C22 - 0.0003 (0.0025) O2 0.6768 (0.0036) C23 0.9882 (0.0046) C24 0.0214 (0.0030) C1 Rms deviation of fitted atoms = 0.0113 |
Refinement. Friedel pairs were merged before refinement. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.1232 (2) | 0.10043 (13) | −0.02160 (7) | 0.0542 (4) | |
O2 | 0.4422 (2) | 0.04635 (15) | 0.13473 (7) | 0.0628 (5) | |
C1 | 0.1294 (3) | 0.13077 (17) | 0.08651 (9) | 0.0418 (5) | |
C2 | 0.1133 (3) | 0.20605 (18) | 0.13934 (10) | 0.0442 (5) | |
C3 | 0.1275 (3) | 0.1659 (2) | 0.20208 (10) | 0.0531 (6) | |
H3 | 0.1505 | 0.0881 | 0.2094 | 0.064* | |
C4 | 0.1084 (4) | 0.2385 (2) | 0.25157 (12) | 0.0657 (7) | |
H4 | 0.1177 | 0.2097 | 0.2921 | 0.079* | |
C5 | 0.0747 (4) | 0.3566 (2) | 0.24208 (13) | 0.0735 (8) | |
H5 | 0.0623 | 0.4059 | 0.2762 | 0.088* | |
C6 | 0.0604 (4) | 0.3983 (2) | 0.18325 (14) | 0.0697 (7) | |
H6 | 0.0379 | 0.4766 | 0.1774 | 0.084* | |
C7 | 0.0788 (3) | 0.32569 (19) | 0.13023 (12) | 0.0552 (6) | |
C8 | 0.0615 (4) | 0.3661 (2) | 0.06835 (12) | 0.0640 (7) | |
H8 | 0.0391 | 0.4442 | 0.0617 | 0.077* | |
C9 | 0.0763 (3) | 0.29544 (18) | 0.01820 (12) | 0.0569 (6) | |
H9 | 0.0644 | 0.3251 | −0.0221 | 0.068* | |
C10 | 0.1097 (3) | 0.17673 (18) | 0.02709 (10) | 0.0449 (5) | |
C11 | 0.0754 (4) | 0.1385 (2) | −0.08307 (11) | 0.0699 (7) | |
H11A | 0.1633 | 0.1919 | −0.0991 | 0.084* | |
H11B | −0.0380 | 0.1776 | −0.0820 | 0.084* | |
C12 | 0.0653 (6) | 0.0341 (3) | −0.12354 (13) | 0.1019 (11) | |
H12A | 0.1806 | 0.0000 | −0.1272 | 0.153* | |
H12B | 0.0234 | 0.0556 | −0.1644 | 0.153* | |
H12C | −0.0146 | −0.0209 | −0.1052 | 0.153* | |
C13 | 0.1598 (3) | 0.00437 (19) | 0.09562 (9) | 0.0427 (5) | |
C14 | 0.0258 (3) | −0.07740 (17) | 0.08004 (9) | 0.0447 (5) | |
C15 | −0.1413 (3) | −0.0444 (2) | 0.05567 (10) | 0.0515 (6) | |
H15 | −0.1649 | 0.0336 | 0.0489 | 0.062* | |
C16 | −0.2684 (4) | −0.1243 (2) | 0.04188 (11) | 0.0632 (7) | |
H16 | −0.3768 | −0.0999 | 0.0261 | 0.076* | |
C17 | −0.2381 (5) | −0.2416 (2) | 0.05099 (13) | 0.0716 (8) | |
H17 | −0.3247 | −0.2953 | 0.0405 | 0.086* | |
C18 | −0.0831 (5) | −0.2769 (2) | 0.07504 (12) | 0.0690 (8) | |
H18 | −0.0648 | −0.3555 | 0.0817 | 0.083* | |
C19 | 0.0539 (4) | −0.19761 (19) | 0.09059 (10) | 0.0541 (6) | |
C20 | 0.2150 (4) | −0.2322 (2) | 0.11621 (13) | 0.0690 (8) | |
H20 | 0.2352 | −0.3106 | 0.1231 | 0.083* | |
C21 | 0.3441 (4) | −0.1546 (2) | 0.13152 (12) | 0.0669 (8) | |
H21 | 0.4499 | −0.1802 | 0.1489 | 0.080* | |
C22 | 0.3164 (3) | −0.0350 (2) | 0.12089 (10) | 0.0523 (6) | |
C23 | 0.5574 (4) | 0.0219 (3) | 0.18695 (13) | 0.0787 (9) | |
H23A | 0.6503 | −0.0310 | 0.1742 | 0.094* | |
H23B | 0.4910 | −0.0138 | 0.2207 | 0.094* | |
C24 | 0.6353 (4) | 0.1329 (3) | 0.20840 (17) | 0.1045 (12) | |
H24A | 0.7045 | 0.1660 | 0.1752 | 0.157* | |
H24B | 0.7095 | 0.1191 | 0.2441 | 0.157* | |
H24C | 0.5423 | 0.1854 | 0.2197 | 0.157* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0689 (10) | 0.0558 (9) | 0.0380 (8) | 0.0021 (8) | −0.0019 (8) | 0.0086 (7) |
O2 | 0.0503 (9) | 0.0787 (11) | 0.0593 (10) | 0.0058 (10) | −0.0098 (8) | 0.0187 (9) |
C1 | 0.0420 (11) | 0.0417 (11) | 0.0419 (11) | 0.0012 (10) | −0.0005 (10) | 0.0057 (10) |
C2 | 0.0391 (11) | 0.0461 (12) | 0.0475 (12) | −0.0046 (10) | 0.0007 (10) | 0.0012 (9) |
C3 | 0.0526 (14) | 0.0607 (14) | 0.0460 (13) | −0.0017 (12) | 0.0025 (11) | 0.0011 (11) |
C4 | 0.0674 (18) | 0.0820 (18) | 0.0478 (13) | −0.0029 (16) | 0.0020 (12) | −0.0105 (13) |
C5 | 0.0778 (19) | 0.0720 (18) | 0.0706 (18) | −0.0048 (16) | 0.0021 (15) | −0.0262 (15) |
C6 | 0.0793 (17) | 0.0482 (14) | 0.0815 (19) | 0.0007 (15) | −0.0032 (16) | −0.0178 (13) |
C7 | 0.0523 (13) | 0.0462 (13) | 0.0670 (16) | −0.0023 (11) | −0.0023 (12) | −0.0016 (11) |
C8 | 0.0789 (18) | 0.0394 (12) | 0.0738 (18) | 0.0033 (13) | −0.0054 (15) | 0.0083 (12) |
C9 | 0.0640 (15) | 0.0504 (13) | 0.0562 (15) | −0.0017 (13) | −0.0064 (12) | 0.0160 (11) |
C10 | 0.0445 (12) | 0.0475 (12) | 0.0427 (11) | −0.0010 (11) | −0.0016 (10) | 0.0055 (10) |
C11 | 0.0831 (19) | 0.0834 (18) | 0.0432 (13) | 0.0114 (16) | −0.0111 (13) | 0.0100 (13) |
C12 | 0.139 (3) | 0.111 (3) | 0.0560 (17) | 0.023 (3) | −0.023 (2) | −0.0091 (17) |
C13 | 0.0485 (13) | 0.0453 (11) | 0.0343 (10) | 0.0066 (11) | 0.0048 (9) | 0.0059 (9) |
C14 | 0.0610 (14) | 0.0397 (11) | 0.0334 (11) | 0.0047 (11) | 0.0084 (10) | 0.0014 (9) |
C15 | 0.0607 (14) | 0.0449 (12) | 0.0488 (13) | −0.0049 (12) | −0.0003 (11) | 0.0015 (10) |
C16 | 0.0744 (17) | 0.0613 (15) | 0.0539 (14) | −0.0147 (14) | −0.0055 (13) | 0.0047 (12) |
C17 | 0.099 (2) | 0.0647 (18) | 0.0509 (15) | −0.0238 (17) | −0.0023 (15) | −0.0006 (13) |
C18 | 0.117 (3) | 0.0384 (12) | 0.0516 (14) | −0.0101 (16) | 0.0171 (17) | −0.0013 (11) |
C19 | 0.0789 (17) | 0.0433 (13) | 0.0400 (12) | 0.0094 (13) | 0.0101 (12) | 0.0042 (10) |
C20 | 0.097 (2) | 0.0458 (14) | 0.0646 (17) | 0.0184 (16) | 0.0120 (16) | 0.0122 (13) |
C21 | 0.0686 (17) | 0.0722 (18) | 0.0601 (16) | 0.0308 (16) | 0.0067 (13) | 0.0190 (14) |
C22 | 0.0529 (13) | 0.0598 (15) | 0.0442 (12) | 0.0098 (12) | 0.0033 (11) | 0.0086 (11) |
C23 | 0.0654 (16) | 0.108 (2) | 0.0628 (16) | 0.0114 (19) | −0.0185 (15) | 0.0162 (16) |
C24 | 0.080 (2) | 0.137 (3) | 0.097 (2) | −0.024 (2) | −0.0357 (19) | 0.023 (2) |
O1—C10 | 1.367 (3) | C12—H12B | 0.9600 |
O1—C11 | 1.430 (3) | C12—H12C | 0.9600 |
O2—C22 | 1.370 (3) | C13—C22 | 1.378 (3) |
O2—C23 | 1.443 (3) | C13—C14 | 1.426 (3) |
C1—C10 | 1.383 (3) | C14—C15 | 1.419 (3) |
C1—C2 | 1.429 (3) | C14—C19 | 1.424 (3) |
C1—C13 | 1.492 (3) | C15—C16 | 1.365 (3) |
C2—C3 | 1.421 (3) | C15—H15 | 0.9300 |
C2—C7 | 1.421 (3) | C16—C17 | 1.388 (4) |
C3—C4 | 1.356 (3) | C16—H16 | 0.9300 |
C3—H3 | 0.9300 | C17—C18 | 1.344 (4) |
C4—C5 | 1.403 (4) | C17—H17 | 0.9300 |
C4—H4 | 0.9300 | C18—C19 | 1.423 (4) |
C5—C6 | 1.349 (4) | C18—H18 | 0.9300 |
C5—H5 | 0.9300 | C19—C20 | 1.394 (4) |
C6—C7 | 1.415 (3) | C20—C21 | 1.366 (4) |
C6—H6 | 0.9300 | C20—H20 | 0.9300 |
C7—C8 | 1.406 (3) | C21—C22 | 1.417 (4) |
C8—C9 | 1.351 (3) | C21—H21 | 0.9300 |
C8—H8 | 0.9300 | C23—C24 | 1.485 (4) |
C9—C10 | 1.408 (3) | C23—H23A | 0.9700 |
C9—H9 | 0.9300 | C23—H23B | 0.9700 |
C11—C12 | 1.486 (4) | C24—H24A | 0.9600 |
C11—H11A | 0.9700 | C24—H24B | 0.9600 |
C11—H11B | 0.9700 | C24—H24C | 0.9600 |
C12—H12A | 0.9600 | ||
C10—O1—C11 | 118.66 (18) | H12B—C12—H12C | 109.5 |
C22—O2—C23 | 116.9 (2) | C22—C13—C14 | 118.9 (2) |
C10—C1—C2 | 118.68 (18) | C22—C13—C1 | 120.4 (2) |
C10—C1—C13 | 120.83 (19) | C14—C13—C1 | 120.6 (2) |
C2—C1—C13 | 120.45 (18) | C15—C14—C19 | 117.0 (2) |
C3—C2—C7 | 117.4 (2) | C15—C14—C13 | 122.72 (19) |
C3—C2—C1 | 122.5 (2) | C19—C14—C13 | 120.3 (2) |
C7—C2—C1 | 120.03 (19) | C16—C15—C14 | 121.6 (2) |
C4—C3—C2 | 121.6 (2) | C16—C15—H15 | 119.2 |
C4—C3—H3 | 119.2 | C14—C15—H15 | 119.2 |
C2—C3—H3 | 119.2 | C15—C16—C17 | 121.0 (3) |
C3—C4—C5 | 120.6 (2) | C15—C16—H16 | 119.5 |
C3—C4—H4 | 119.7 | C17—C16—H16 | 119.5 |
C5—C4—H4 | 119.7 | C18—C17—C16 | 119.6 (3) |
C6—C5—C4 | 119.8 (2) | C18—C17—H17 | 120.2 |
C6—C5—H5 | 120.1 | C16—C17—H17 | 120.2 |
C4—C5—H5 | 120.1 | C17—C18—C19 | 121.9 (2) |
C5—C6—C7 | 121.6 (2) | C17—C18—H18 | 119.1 |
C5—C6—H6 | 119.2 | C19—C18—H18 | 119.1 |
C7—C6—H6 | 119.2 | C20—C19—C18 | 122.9 (2) |
C8—C7—C6 | 123.0 (2) | C20—C19—C14 | 118.2 (2) |
C8—C7—C2 | 118.0 (2) | C18—C19—C14 | 118.9 (3) |
C6—C7—C2 | 119.1 (2) | C21—C20—C19 | 122.0 (2) |
C9—C8—C7 | 122.3 (2) | C21—C20—H20 | 119.0 |
C9—C8—H8 | 118.8 | C19—C20—H20 | 119.0 |
C7—C8—H8 | 118.8 | C20—C21—C22 | 119.8 (3) |
C8—C9—C10 | 119.8 (2) | C20—C21—H21 | 120.1 |
C8—C9—H9 | 120.1 | C22—C21—H21 | 120.1 |
C10—C9—H9 | 120.1 | O2—C22—C13 | 117.1 (2) |
O1—C10—C1 | 116.16 (18) | O2—C22—C21 | 122.2 (2) |
O1—C10—C9 | 122.69 (19) | C13—C22—C21 | 120.8 (2) |
C1—C10—C9 | 121.1 (2) | O2—C23—C24 | 108.0 (2) |
O1—C11—C12 | 107.2 (2) | O2—C23—H23A | 110.1 |
O1—C11—H11A | 110.3 | C24—C23—H23A | 110.1 |
C12—C11—H11A | 110.3 | O2—C23—H23B | 110.1 |
O1—C11—H11B | 110.3 | C24—C23—H23B | 110.1 |
C12—C11—H11B | 110.3 | H23A—C23—H23B | 108.4 |
H11A—C11—H11B | 108.5 | C23—C24—H24A | 109.5 |
C11—C12—H12A | 109.5 | C23—C24—H24B | 109.5 |
C11—C12—H12B | 109.5 | H24A—C24—H24B | 109.5 |
H12A—C12—H12B | 109.5 | C23—C24—H24C | 109.5 |
C11—C12—H12C | 109.5 | H24A—C24—H24C | 109.5 |
H12A—C12—H12C | 109.5 | H24B—C24—H24C | 109.5 |
C10—C1—C2—C3 | 178.5 (2) | C10—C1—C13—C14 | −66.4 (3) |
C13—C1—C2—C3 | 0.9 (3) | C2—C1—C13—C14 | 111.3 (2) |
C10—C1—C2—C7 | −0.3 (3) | C22—C13—C14—C15 | 178.00 (19) |
C13—C1—C2—C7 | −178.0 (2) | C1—C13—C14—C15 | −0.2 (3) |
C7—C2—C3—C4 | 0.2 (3) | C22—C13—C14—C19 | 0.1 (3) |
C1—C2—C3—C4 | −178.7 (2) | C1—C13—C14—C19 | −178.16 (19) |
C2—C3—C4—C5 | −0.4 (4) | C19—C14—C15—C16 | −1.1 (3) |
C3—C4—C5—C6 | 0.3 (5) | C13—C14—C15—C16 | −179.1 (2) |
C4—C5—C6—C7 | −0.1 (5) | C14—C15—C16—C17 | −0.3 (4) |
C5—C6—C7—C8 | 178.8 (3) | C15—C16—C17—C18 | 1.5 (4) |
C5—C6—C7—C2 | −0.1 (4) | C16—C17—C18—C19 | −1.2 (4) |
C3—C2—C7—C8 | −179.0 (2) | C17—C18—C19—C20 | 179.3 (2) |
C1—C2—C7—C8 | 0.0 (3) | C17—C18—C19—C14 | −0.3 (4) |
C3—C2—C7—C6 | 0.0 (3) | C15—C14—C19—C20 | −178.2 (2) |
C1—C2—C7—C6 | 178.9 (2) | C13—C14—C19—C20 | −0.1 (3) |
C6—C7—C8—C9 | −178.8 (3) | C15—C14—C19—C18 | 1.4 (3) |
C2—C7—C8—C9 | 0.1 (4) | C13—C14—C19—C18 | 179.47 (19) |
C7—C8—C9—C10 | 0.2 (4) | C18—C19—C20—C21 | −179.2 (2) |
C11—O1—C10—C1 | 169.8 (2) | C14—C19—C20—C21 | 0.3 (4) |
C11—O1—C10—C9 | −9.7 (3) | C19—C20—C21—C22 | −0.5 (4) |
C2—C1—C10—O1 | −178.86 (18) | C23—O2—C22—C13 | 148.9 (2) |
C13—C1—C10—O1 | −1.2 (3) | C23—O2—C22—C21 | −31.4 (3) |
C2—C1—C10—C9 | 0.6 (3) | C14—C13—C22—O2 | 179.51 (18) |
C13—C1—C10—C9 | 178.3 (2) | C1—C13—C22—O2 | −2.3 (3) |
C8—C9—C10—O1 | 178.9 (2) | C14—C13—C22—C21 | −0.2 (3) |
C8—C9—C10—C1 | −0.6 (4) | C1—C13—C22—C21 | 178.0 (2) |
C10—O1—C11—C12 | −168.1 (2) | C20—C21—C22—O2 | −179.3 (2) |
C10—C1—C13—C22 | 115.5 (2) | C20—C21—C22—C13 | 0.4 (4) |
C2—C1—C13—C22 | −66.9 (3) | C22—O2—C23—C24 | −159.7 (2) |