Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804022445/cv6374sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804022445/cv6374IIsup2.hkl |
CCDC reference: 253004
Data collection: WinAFC Diffractometer Control Software (Rigaku, 1999); cell refinement: WinAFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 2001); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN.
C30H24O2 | F(000) = 880 |
Mr = 416.52 | Dx = 1.248 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 14.883 (4) Å | Cell parameters from 25 reflections |
b = 11.290 (5) Å | θ = 10.3–13.6° |
c = 13.418 (4) Å | µ = 0.08 mm−1 |
β = 100.52 (2)° | T = 300 K |
V = 2216.7 (13) Å3 | Needle, pale orange |
Z = 4 | 0.45 × 0.25 × 0.10 mm |
Rigaku AFC7R diffractometer | Rint = 0.027 |
ω–2θ scans | θmax = 27.5° |
Absorption correction: integration (Coppens et al., 1965) | h = −7→19 |
Tmin = 0.982, Tmax = 0.993 | k = 0→14 |
5794 measured reflections | l = −17→17 |
5088 independent reflections | 3 standard reflections every 150 reflections |
1507 reflections with I > 2σ(I) | intensity decay: 0.3% |
Refinement on F2 | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.057 | w = 1/[σ2(Fo2) + (0.0548P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.170 | (Δ/σ)max < 0.001 |
S = 0.92 | Δρmax = 0.23 e Å−3 |
5088 reflections | Δρmin = −0.22 e Å−3 |
290 parameters |
Refinement. Refinement using reflections with F2 > 0.0 σ(F2). The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt). |
x | y | z | Uiso*/Ueq | ||
O1 | −0.0245 (2) | −0.0461 (3) | 0.8157 (2) | 0.092 (1) | |
O2 | −0.0419 (2) | 0.1248 (3) | 0.9664 (2) | 0.100 (1) | |
C3 | −0.0662 (2) | 0.0415 (3) | 0.7545 (3) | 0.054 (1) | |
C4 | −0.0090 (2) | 0.1537 (3) | 0.7451 (2) | 0.0461 (9) | |
C5 | −0.0396 (2) | 0.1965 (3) | 0.6335 (2) | 0.0448 (9) | |
C6 | −0.0816 (2) | 0.0872 (3) | 0.5801 (3) | 0.0464 (9) | |
C7 | −0.0948 (2) | −0.0007 (3) | 0.6472 (3) | 0.0487 (9) | |
C8 | −0.1306 (3) | −0.1095 (4) | 0.6150 (3) | 0.063 (1) | |
C9 | −0.1549 (3) | −0.1295 (4) | 0.5116 (3) | 0.070 (1) | |
C10 | −0.1440 (3) | −0.0419 (4) | 0.4439 (3) | 0.066 (1) | |
C11 | −0.1066 (3) | 0.0663 (4) | 0.4767 (3) | 0.057 (1) | |
C12 | 0.0009 (3) | 0.2058 (4) | 0.9370 (3) | 0.059 (1) | |
C13 | −0.0066 (2) | 0.2466 (3) | 0.8275 (2) | 0.0446 (9) | |
C14 | 0.0666 (2) | 0.3463 (3) | 0.8318 (2) | 0.0487 (9) | |
C15 | 0.0832 (2) | 0.3821 (3) | 0.9424 (3) | 0.0486 (9) | |
C16 | 0.0482 (2) | 0.3013 (3) | 1.0009 (3) | 0.0472 (9) | |
C17 | 0.0578 (3) | 0.3146 (4) | 1.1055 (3) | 0.060 (1) | |
C18 | 0.1044 (3) | 0.4121 (4) | 1.1494 (3) | 0.070 (1) | |
C19 | 0.1408 (3) | 0.4929 (4) | 1.0903 (4) | 0.070 (1) | |
C20 | 0.1306 (3) | 0.4792 (3) | 0.9865 (3) | 0.060 (1) | |
C21 | −0.1040 (2) | 0.3021 (3) | 0.6181 (2) | 0.0443 (9) | |
C22 | −0.0767 (3) | 0.4085 (4) | 0.5837 (3) | 0.055 (1) | |
C23 | −0.1347 (3) | 0.5053 (4) | 0.5675 (3) | 0.069 (1) | |
C24 | −0.2224 (3) | 0.4965 (4) | 0.5859 (3) | 0.066 (1) | |
C25 | −0.2509 (3) | 0.3919 (4) | 0.6208 (3) | 0.063 (1) | |
C26 | −0.1931 (3) | 0.2954 (3) | 0.6362 (3) | 0.0538 (10) | |
C27 | 0.1553 (2) | 0.3116 (3) | 0.7979 (3) | 0.0451 (9) | |
C28 | 0.2099 (3) | 0.2226 (3) | 0.8467 (3) | 0.055 (1) | |
C29 | 0.2913 (3) | 0.1951 (4) | 0.8176 (4) | 0.072 (1) | |
C30 | 0.3209 (3) | 0.2566 (6) | 0.7416 (4) | 0.088 (2) | |
C31 | 0.2679 (4) | 0.3441 (5) | 0.6932 (3) | 0.088 (2) | |
C32 | 0.1852 (3) | 0.3719 (4) | 0.7209 (3) | 0.066 (1) | |
H1 | −0.0296 | −0.0325 | 0.8745 | 0.0922* | |
H3 | −0.1196 | 0.0647 | 0.7789 | 0.0645* | |
H4 | 0.0522 | 0.1271 | 0.7500 | 0.0553* | |
H5 | 0.0135 | 0.2160 | 0.6070 | 0.0538* | |
H8 | −0.1383 | −0.1694 | 0.6624 | 0.0758* | |
H9 | −0.1793 | −0.2041 | 0.4875 | 0.0837* | |
H10 | −0.1625 | −0.0559 | 0.3733 | 0.0787* | |
H11 | −0.0980 | 0.1257 | 0.4291 | 0.0687* | |
H13 | −0.0638 | 0.2861 | 0.8117 | 0.0536* | |
H14 | 0.0402 | 0.4113 | 0.7920 | 0.0584* | |
H17 | 0.0329 | 0.2581 | 1.1453 | 0.0714* | |
H18 | 0.1116 | 0.4240 | 1.2205 | 0.0834* | |
H19 | 0.1735 | 0.5593 | 1.1217 | 0.0844* | |
H20 | 0.1557 | 0.5353 | 0.9465 | 0.0720* | |
H22 | −0.0163 | 0.4159 | 0.5707 | 0.0662* | |
H23 | −0.1139 | 0.5777 | 0.5437 | 0.0833* | |
H24 | −0.2626 | 0.5624 | 0.5744 | 0.0793* | |
H25 | −0.3110 | 0.3856 | 0.6347 | 0.0755* | |
H26 | −0.2145 | 0.2231 | 0.6594 | 0.0645* | |
H28 | 0.1912 | 0.1802 | 0.9006 | 0.0663* | |
H29 | 0.3276 | 0.1325 | 0.8506 | 0.0860* | |
H30 | 0.3779 | 0.2380 | 0.7231 | 0.1061* | |
H31 | 0.2876 | 0.3867 | 0.6400 | 0.1057* | |
H32 | 0.1486 | 0.4334 | 0.6862 | 0.0795* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.144 (3) | 0.069 (2) | 0.054 (2) | −0.023 (2) | −0.006 (2) | 0.010 (2) |
O2 | 0.154 (3) | 0.096 (2) | 0.045 (2) | −0.054 (2) | 0.009 (2) | 0.005 (2) |
C3 | 0.059 (3) | 0.049 (2) | 0.049 (2) | 0.002 (2) | −0.003 (2) | 0.001 (2) |
C4 | 0.047 (2) | 0.050 (2) | 0.040 (2) | −0.003 (2) | 0.001 (2) | −0.002 (2) |
C5 | 0.046 (2) | 0.050 (2) | 0.039 (2) | 0.005 (2) | 0.008 (2) | 0.002 (2) |
C6 | 0.043 (2) | 0.055 (3) | 0.039 (2) | 0.010 (2) | 0.003 (2) | −0.009 (2) |
C7 | 0.045 (2) | 0.049 (2) | 0.049 (2) | 0.003 (2) | 0.003 (2) | −0.009 (2) |
C8 | 0.064 (3) | 0.052 (3) | 0.070 (3) | −0.001 (2) | 0.003 (2) | −0.011 (2) |
C9 | 0.063 (3) | 0.066 (3) | 0.073 (3) | 0.012 (2) | −0.008 (2) | −0.028 (3) |
C10 | 0.057 (3) | 0.078 (3) | 0.053 (3) | 0.023 (3) | −0.012 (2) | −0.026 (3) |
C11 | 0.056 (3) | 0.067 (3) | 0.047 (2) | 0.022 (2) | 0.003 (2) | −0.007 (2) |
C12 | 0.066 (3) | 0.065 (3) | 0.047 (2) | −0.014 (2) | 0.015 (2) | −0.002 (2) |
C13 | 0.044 (2) | 0.050 (2) | 0.038 (2) | 0.000 (2) | 0.004 (2) | −0.002 (2) |
C14 | 0.053 (2) | 0.045 (2) | 0.045 (2) | 0.002 (2) | 0.002 (2) | 0.002 (2) |
C15 | 0.047 (2) | 0.044 (2) | 0.052 (2) | 0.006 (2) | 0.003 (2) | −0.007 (2) |
C16 | 0.049 (2) | 0.048 (2) | 0.042 (2) | 0.004 (2) | 0.001 (2) | −0.007 (2) |
C17 | 0.064 (3) | 0.066 (3) | 0.046 (2) | 0.014 (2) | 0.003 (2) | −0.008 (2) |
C18 | 0.067 (3) | 0.084 (3) | 0.051 (2) | 0.019 (3) | −0.006 (2) | −0.025 (3) |
C19 | 0.051 (3) | 0.072 (3) | 0.084 (3) | 0.008 (2) | 0.004 (2) | −0.039 (3) |
C20 | 0.054 (3) | 0.053 (3) | 0.073 (3) | 0.003 (2) | 0.011 (2) | −0.016 (2) |
C21 | 0.046 (2) | 0.052 (2) | 0.034 (2) | 0.001 (2) | 0.004 (2) | 0.003 (2) |
C22 | 0.060 (3) | 0.058 (3) | 0.049 (2) | 0.006 (2) | 0.016 (2) | 0.011 (2) |
C23 | 0.097 (4) | 0.054 (3) | 0.060 (3) | 0.004 (3) | 0.021 (2) | 0.013 (2) |
C24 | 0.082 (3) | 0.061 (3) | 0.052 (3) | 0.024 (3) | 0.007 (2) | −0.001 (2) |
C25 | 0.050 (3) | 0.069 (3) | 0.068 (3) | 0.009 (3) | 0.007 (2) | −0.012 (2) |
C26 | 0.050 (2) | 0.055 (3) | 0.057 (2) | −0.002 (2) | 0.010 (2) | −0.004 (2) |
C27 | 0.046 (2) | 0.041 (2) | 0.046 (2) | −0.008 (2) | 0.004 (2) | −0.003 (2) |
C28 | 0.058 (3) | 0.055 (3) | 0.053 (2) | 0.000 (2) | 0.011 (2) | −0.004 (2) |
C29 | 0.057 (3) | 0.068 (3) | 0.088 (3) | 0.006 (2) | 0.008 (2) | −0.022 (3) |
C30 | 0.056 (3) | 0.129 (5) | 0.084 (4) | −0.018 (3) | 0.023 (3) | −0.040 (4) |
C31 | 0.074 (4) | 0.132 (5) | 0.064 (3) | −0.039 (3) | 0.029 (3) | −0.005 (3) |
C32 | 0.067 (3) | 0.075 (3) | 0.057 (2) | −0.023 (2) | 0.011 (2) | 0.006 (2) |
O1—C3 | 1.361 (5) | C16—C17 | 1.393 (5) |
O1—H1 | 0.820 | C17—C18 | 1.375 (6) |
O2—C12 | 1.219 (6) | C17—H17 | 0.950 |
C3—C4 | 1.544 (5) | C18—C19 | 1.382 (7) |
C3—C7 | 1.501 (5) | C18—H18 | 0.950 |
C3—H3 | 0.950 | C19—C20 | 1.382 (6) |
C4—C5 | 1.561 (4) | C19—H19 | 0.950 |
C4—C13 | 1.519 (5) | C20—H20 | 0.950 |
C4—H4 | 0.950 | C21—C22 | 1.375 (5) |
C5—C6 | 1.504 (5) | C21—C26 | 1.392 (5) |
C5—C21 | 1.520 (5) | C22—C23 | 1.385 (6) |
C5—H5 | 0.950 | C22—H22 | 0.950 |
C6—C7 | 1.378 (5) | C23—C24 | 1.376 (7) |
C6—C11 | 1.390 (5) | C23—H23 | 0.950 |
C7—C8 | 1.377 (5) | C24—C25 | 1.367 (6) |
C8—C9 | 1.388 (6) | C24—H24 | 0.950 |
C8—H8 | 0.950 | C25—C26 | 1.380 (6) |
C9—C10 | 1.373 (6) | C25—H25 | 0.950 |
C9—H9 | 0.950 | C26—H26 | 0.950 |
C10—C11 | 1.380 (6) | C27—C28 | 1.380 (5) |
C10—H10 | 0.950 | C27—C32 | 1.378 (6) |
C11—H11 | 0.950 | C28—C29 | 1.375 (6) |
C12—C13 | 1.525 (5) | C28—H28 | 0.950 |
C12—C16 | 1.475 (5) | C29—C30 | 1.371 (8) |
C13—C14 | 1.560 (5) | C29—H29 | 0.950 |
C13—H13 | 0.950 | C30—C31 | 1.354 (8) |
C14—C15 | 1.515 (5) | C30—H30 | 0.950 |
C14—C27 | 1.523 (5) | C31—C32 | 1.385 (7) |
C14—H14 | 0.950 | C31—H31 | 0.950 |
C15—C16 | 1.366 (5) | C32—H32 | 0.950 |
C15—C20 | 1.377 (5) | ||
C3—O1—H1 | 109.5 | C14—C15—C20 | 127.7 (3) |
O1—C3—C4 | 116.6 (3) | C16—C15—C20 | 120.3 (3) |
O1—C3—C7 | 111.5 (3) | C12—C16—C15 | 110.3 (3) |
O1—C3—H3 | 108.1 | C12—C16—C17 | 127.9 (3) |
C4—C3—C7 | 104.3 (3) | C15—C16—C17 | 121.8 (3) |
C4—C3—H3 | 108.1 | C16—C17—C18 | 118.0 (4) |
C7—C3—H3 | 108.1 | C16—C17—H17 | 121.0 |
C3—C4—C5 | 105.2 (3) | C18—C17—H17 | 121.0 |
C3—C4—C13 | 116.6 (3) | C17—C18—C19 | 120.1 (4) |
C3—C4—H4 | 105.8 | C17—C18—H18 | 119.9 |
C5—C4—C13 | 116.6 (3) | C19—C18—H18 | 119.9 |
C5—C4—H4 | 105.8 | C18—C19—C20 | 121.4 (4) |
C13—C4—H4 | 105.8 | C18—C19—H19 | 119.3 |
C4—C5—C6 | 103.1 (3) | C20—C19—H19 | 119.3 |
C4—C5—C21 | 116.1 (3) | C15—C20—C19 | 118.4 (4) |
C4—C5—H5 | 108.3 | C15—C20—H20 | 120.8 |
C6—C5—C21 | 112.4 (3) | C19—C20—H20 | 120.8 |
C6—C5—H5 | 108.3 | C5—C21—C22 | 120.9 (3) |
C21—C5—H5 | 108.3 | C5—C21—C26 | 122.0 (3) |
C5—C6—C7 | 112.0 (3) | C22—C21—C26 | 117.1 (3) |
C5—C6—C11 | 128.9 (3) | C21—C22—C23 | 121.9 (4) |
C7—C6—C11 | 119.1 (3) | C21—C22—H22 | 119.1 |
C3—C7—C6 | 110.4 (3) | C23—C22—H22 | 119.0 |
C3—C7—C8 | 127.5 (3) | C22—C23—C24 | 120.0 (4) |
C6—C7—C8 | 122.0 (3) | C22—C23—H23 | 120.0 |
C7—C8—C9 | 118.3 (4) | C24—C23—H23 | 120.0 |
C7—C8—H8 | 120.8 | C23—C24—C25 | 119.2 (4) |
C9—C8—H8 | 120.8 | C23—C24—H24 | 120.4 |
C8—C9—C10 | 120.2 (4) | C25—C24—H24 | 120.4 |
C8—C9—H9 | 119.9 | C24—C25—C26 | 120.6 (4) |
C10—C9—H9 | 119.9 | C24—C25—H25 | 119.7 |
C9—C10—C11 | 121.1 (4) | C26—C25—H25 | 119.7 |
C9—C10—H10 | 119.4 | C21—C26—C25 | 121.2 (4) |
C11—C10—H10 | 119.5 | C21—C26—H26 | 119.4 |
C6—C11—C10 | 119.2 (4) | C25—C26—H26 | 119.4 |
C6—C11—H11 | 120.4 | C14—C27—C28 | 120.8 (3) |
C10—C11—H11 | 120.4 | C14—C27—C32 | 120.9 (3) |
O2—C12—C13 | 126.0 (3) | C28—C27—C32 | 118.2 (4) |
O2—C12—C16 | 125.6 (3) | C27—C28—C29 | 120.2 (4) |
C13—C12—C16 | 106.4 (3) | C27—C28—H28 | 119.9 |
C4—C13—C12 | 118.7 (3) | C29—C28—H28 | 119.9 |
C4—C13—C14 | 116.7 (3) | C28—C29—C30 | 121.1 (4) |
C4—C13—H13 | 105.1 | C28—C29—H29 | 119.5 |
C12—C13—C14 | 104.7 (3) | C30—C29—H29 | 119.4 |
C12—C13—H13 | 105.2 | C29—C30—C31 | 119.2 (5) |
C14—C13—H13 | 105.1 | C29—C30—H30 | 120.4 |
C13—C14—C15 | 102.5 (3) | C31—C30—H30 | 120.4 |
C13—C14—C27 | 116.1 (3) | C30—C31—C32 | 120.3 (5) |
C13—C14—H14 | 108.8 | C30—C31—H31 | 119.8 |
C15—C14—C27 | 111.5 (3) | C32—C31—H31 | 119.8 |
C15—C14—H14 | 108.8 | C27—C32—C31 | 121.0 (4) |
C27—C14—H14 | 108.8 | C27—C32—H32 | 119.5 |
C14—C15—C16 | 111.9 (3) | C31—C32—H32 | 119.5 |
O1—C3—C4—C5 | 145.2 (3) | C11—C6—C5—C21 | 66.4 (5) |
O1—C3—C4—C13 | −83.9 (4) | C12—C13—C14—C15 | −19.6 (3) |
O1—C3—C7—C6 | −141.9 (3) | C12—C13—C14—C27 | 102.2 (3) |
O1—C3—C7—C8 | 38.8 (5) | C12—C16—C15—C14 | −2.6 (4) |
O2—C12—C13—C4 | −44.2 (6) | C12—C16—C15—C20 | −179.9 (3) |
O2—C12—C13—C14 | −176.5 (4) | C12—C16—C17—C18 | −179.4 (4) |
O2—C12—C16—C15 | −175.4 (4) | C13—C4—C5—C21 | −27.9 (4) |
O2—C12—C16—C17 | 3.8 (7) | C13—C12—C16—C15 | −10.7 (4) |
C3—C4—C5—C6 | −20.3 (3) | C13—C12—C16—C17 | 168.5 (4) |
C3—C4—C5—C21 | 103.0 (3) | C13—C14—C15—C16 | 14.3 (4) |
C3—C4—C13—C12 | 40.5 (4) | C13—C14—C15—C20 | −168.7 (4) |
C3—C4—C13—C14 | 167.3 (3) | C13—C14—C27—C28 | −59.9 (4) |
C3—C7—C6—C5 | 2.2 (4) | C13—C14—C27—C32 | 123.2 (3) |
C3—C7—C6—C11 | −178.2 (3) | C14—C13—C12—C16 | 18.9 (4) |
C3—C7—C8—C9 | 178.3 (4) | C14—C15—C16—C17 | 178.2 (3) |
C4—C3—C7—C6 | −15.3 (4) | C14—C15—C20—C19 | −177.4 (4) |
C4—C3—C7—C8 | 165.4 (4) | C14—C27—C28—C29 | −177.7 (3) |
C4—C5—C6—C7 | 11.7 (4) | C14—C27—C32—C31 | 176.9 (4) |
C4—C5—C6—C11 | −167.9 (4) | C15—C14—C27—C28 | 57.0 (4) |
C4—C5—C21—C22 | 114.1 (4) | C15—C14—C27—C32 | −119.9 (4) |
C4—C5—C21—C26 | −67.1 (4) | C15—C16—C17—C18 | −0.3 (6) |
C4—C13—C12—C16 | 151.2 (3) | C15—C20—C19—C18 | −0.2 (6) |
C4—C13—C14—C15 | −153.1 (3) | C16—C15—C14—C27 | −110.7 (3) |
C4—C13—C14—C27 | −31.2 (4) | C16—C15—C20—C19 | −0.7 (5) |
C5—C4—C3—C7 | 21.8 (3) | C16—C17—C18—C19 | −0.6 (6) |
C5—C4—C13—C12 | 165.9 (3) | C17—C16—C15—C20 | 0.9 (6) |
C5—C4—C13—C14 | −67.3 (4) | C17—C18—C19—C20 | 0.8 (6) |
C5—C6—C7—C8 | −178.5 (3) | C20—C15—C14—C27 | 66.3 (5) |
C5—C6—C11—C10 | 179.6 (4) | C21—C22—C23—C24 | 0.0 (6) |
C5—C21—C22—C23 | 178.9 (3) | C21—C26—C25—C24 | 1.0 (6) |
C5—C21—C26—C25 | −179.4 (3) | C22—C21—C26—C25 | −0.5 (5) |
C6—C5—C4—C13 | −151.3 (3) | C22—C23—C24—C25 | 0.5 (6) |
C6—C5—C21—C22 | −127.6 (3) | C23—C22—C21—C26 | 0.0 (5) |
C6—C5—C21—C26 | 51.3 (4) | C23—C24—C25—C26 | −1.0 (6) |
C6—C7—C8—C9 | −0.9 (6) | C27—C28—C29—C30 | 1.5 (6) |
C6—C11—C10—C9 | −1.5 (6) | C27—C32—C31—C30 | 0.1 (7) |
C7—C3—C4—C13 | 152.8 (3) | C28—C27—C32—C31 | −0.1 (6) |
C7—C6—C5—C21 | −114.1 (3) | C28—C29—C30—C31 | −1.5 (7) |
C7—C6—C11—C10 | 0.1 (5) | C29—C28—C27—C32 | −0.7 (5) |
C7—C8—C9—C10 | −0.5 (6) | C29—C30—C31—C32 | 0.7 (8) |
C8—C7—C6—C11 | 1.1 (6) | C29—C30—C31—C32 | 0.7 (8) |
C8—C9—C10—C11 | 1.7 (6) |