Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520618014981/px5005sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520618014981/px5005Isup2.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2052520618014981/px5005sup3.pdf |
CCDC reference: 1554720
Data collection: 'CrysAlis PRO, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01)' _computing_cell_refinement 'CrysAlis PRO, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01)'; data reduction: 'CrysAlis PRO, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01)'; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: XD2006 (Volkov et al., 2006); molecular graphics: XD2006 (Volkov et al., 2006); software used to prepare material for publication: XD2006 (Volkov et al., 2006).
C20H30O5 | F(000) = 380 |
Mr = 350.44 | Dx = 1.264 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 48814 reflections |
a = 6.5162 (1) Å | θ = 3.1–51.3° |
b = 7.9477 (1) Å | µ = 0.09 mm−1 |
c = 17.9185 (2) Å | T = 110 K |
β = 97.023 (1)° | Plate, colorless |
V = 921.02 (2) Å3 | 0.43 × 0.28 × 0.23 mm |
Z = 2 |
Xcalibur, Eos, Nova diffractometer | 19407 independent reflections |
Radiation source: fine-focus sealed tube | 16923 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.052 |
ω scans | θmax = 50.1°, θmin = 2.8° |
Absorption correction: analytical 'CrysAlisPro, Agilent Technologies,' Version 1.171.38.41 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.' | h = −14→14 |
Tmin = 0.954, Tmax = 0.982 | k = −17→17 |
113191 measured reflections | l = −39→39 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters not defined? |
R[F2 > 2σ(F2)] = 0.034 | w2 = 1/[s2(Fo2)] |
wR(F2) = 0.068 | (Δ/σ)max = 0.001 |
S = 1.53 | Δρmax = 0.27 e Å−3 |
15841 reflections | Δρmin = −0.20 e Å−3 |
255 parameters |
x | y | z | Uiso*/Ueq | ||
O1 | 0.62097 (7) | 0.4697 (3) | 0.06923 (2) | 0.030 | |
O2 | 0.38461 (5) | 0.7408 (3) | 0.042046 (19) | 0.023 | |
O3 | 1.62202 (5) | 0.9712 (3) | 0.586364 (17) | 0.019 | |
O4 | 1.15551 (5) | 1.0790 (3) | 0.55011 (2) | 0.021 | |
O5 | 1.75414 (5) | 1.0221 (3) | 0.479101 (19) | 0.020 | |
C1 | 0.75329 (6) | 0.7592 (3) | 0.096526 (18) | 0.015 | |
C2 | 0.91218 (5) | 0.8561 (3) | 0.153886 (18) | 0.013 | |
C3 | 0.90739 (5) | 0.8166 (3) | 0.239090 (17) | 0.011 | |
C4 | 0.91911 (7) | 0.6243 (3) | 0.24956 (2) | 0.018 | |
C5 | 0.75326 (8) | 0.5308 (3) | 0.19784 (2) | 0.023 | |
C6 | 0.77060 (7) | 0.5689 (3) | 0.11589 (2) | 0.020 | |
C7 | 0.52972 (6) | 0.8226 (3) | 0.09725 (2) | 0.019 | |
C8 | 0.81527 (7) | 0.7821 (3) | 0.01690 (2) | 0.024 | |
C9 | 0.91635 (8) | 1.0466 (3) | 0.13947 (2) | 0.023 | |
C10 | 1.10244 (9) | 1.1289 (3) | 0.18664 (3) | 0.025 | |
C11 | 1.10498 (7) | 1.0853 (3) | 0.26856 (2) | 0.018 | |
C12 | 1.10533 (5) | 0.8983 (3) | 0.283162 (17) | 0.012 | |
C13 | 0.71747 (6) | 0.8838 (3) | 0.27238 (2) | 0.020 | |
C14 | 1.09684 (9) | 1.2023 (3) | 0.32186 (3) | 0.028 | |
C15 | 1.13990 (5) | 0.8520 (3) | 0.367064 (18) | 0.014 | |
C16 | 1.34581 (5) | 0.9090 (3) | 0.404611 (19) | 0.014 | |
C17 | 1.39547 (5) | 0.9356 (3) | 0.478397 (18) | 0.012 | |
C18 | 1.60732 (5) | 0.9801 (3) | 0.51101 (2) | 0.014 | |
C19 | 1.43074 (7) | 0.9041 (3) | 0.60924 (2) | 0.022 | |
C20 | 1.26425 (6) | 0.9259 (3) | 0.541897 (19) | 0.015 | |
H1 | 0.506745 | 0.54078 | 0.049305 | 0.037 | |
H2 | 1.06341 | 0.80798 | 0.142496 | 0.031 | |
H4A | 0.907999 | 0.59959 | 0.308944 | 0.034 | |
H4B | 1.068251 | 0.585013 | 0.233617 | 0.038 | |
H5A | 0.597765 | 0.563233 | 0.209955 | 0.042 | |
H5B | 0.759907 | 0.396067 | 0.209683 | 0.037 | |
H6 | 0.924678 | 0.526505 | 0.104709 | 0.038 | |
H7A | 0.466281 | 0.804292 | 0.150274 | 0.043 | |
H7B | 0.531281 | 0.959022 | 0.08923 | 0.041 | |
H8A | 0.726735 | 0.704466 | −0.022849 | 0.047 | |
H8B | 0.975422 | 0.759705 | 0.016182 | 0.053 | |
H8C | 0.801519 | 0.907737 | −0.002926 | 0.042 | |
H9A | 0.769426 | 1.09645 | 0.153388 | 0.040 | |
H9B | 0.918469 | 1.073017 | 0.079763 | 0.040 | |
H10A | 1.09724 | 1.265703 | 0.181008 | 0.044 | |
H10B | 1.244737 | 1.076023 | 0.16978 | 0.045 | |
H12 | 1.230094 | 0.842795 | 0.255073 | 0.027 | |
H13A | 0.581643 | 0.813019 | 0.256362 | 0.048 | |
H13B | 0.680988 | 1.009121 | 0.255112 | 0.048 | |
H13C | 0.749813 | 0.880967 | 0.331692 | 0.046 | |
H14A | 1.088869 | 1.182446 | 0.380852 | 0.039 | |
H14B | 1.088518 | 1.333576 | 0.307059 | 0.045 | |
H15A | 1.022687 | 0.895735 | 0.401202 | 0.032 | |
H15B | 1.140514 | 0.714704 | 0.370307 | 0.027 | |
H16 | 1.470135 | 0.913437 | 0.370148 | 0.031 | |
H19A | 1.388335 | 0.974377 | 0.657388 | 0.042 | |
H19B | 1.460947 | 0.77259 | 0.624937 | 0.041 | |
H20 | 1.158696 | 0.817758 | 0.540769 | 0.035 | |
H21 | 1.019708 | 1.065311 | 0.522365 | 0.036 | |
H22 | 0.371126 | 0.812604 | −0.001829 | 0.036 |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.03428 (19) | 0.02658 (16) | 0.02544 (15) | 0.00135 (15) | −0.01653 (14) | −0.00946 (13) |
O2 | 0.01551 (11) | 0.03119 (16) | 0.01907 (12) | −0.00134 (11) | −0.00703 (9) | 0.00395 (11) |
O3 | 0.01637 (11) | 0.02331 (13) | 0.01411 (10) | 0.00112 (10) | −0.00601 (8) | −0.00145 (9) |
O4 | 0.01441 (11) | 0.02469 (14) | 0.02288 (13) | 0.00438 (10) | −0.00103 (9) | −0.00966 (11) |
O5 | 0.01147 (10) | 0.02380 (14) | 0.02270 (13) | −0.00197 (9) | −0.00144 (9) | −0.00060 (11) |
C1 | 0.01249 (12) | 0.02372 (16) | 0.00874 (10) | 0.00286 (11) | −0.00181 (9) | −0.00120 (10) |
C2 | 0.01165 (11) | 0.01917 (13) | 0.00866 (10) | 0.00115 (10) | −0.00007 (8) | 0.00122 (9) |
C3 | 0.00988 (10) | 0.01542 (12) | 0.00817 (9) | −0.00009 (9) | −0.00013 (8) | −0.00053 (9) |
C4 | 0.02110 (16) | 0.01594 (13) | 0.01342 (12) | −0.00359 (11) | −0.00636 (11) | 0.00162 (10) |
C5 | 0.02713 (19) | 0.01935 (15) | 0.01815 (15) | −0.00685 (14) | −0.00882 (13) | 0.00060 (12) |
C6 | 0.02134 (16) | 0.02183 (16) | 0.01562 (13) | 0.00297 (13) | −0.00768 (12) | −0.00533 (12) |
C7 | 0.01277 (12) | 0.02974 (19) | 0.01273 (12) | 0.00438 (12) | −0.00232 (10) | −0.00008 (12) |
C8 | 0.01868 (16) | 0.0442 (3) | 0.00894 (11) | 0.00375 (16) | −0.00007 (10) | −0.00140 (14) |
C9 | 0.02637 (19) | 0.02185 (17) | 0.01770 (14) | −0.00333 (14) | −0.00609 (13) | 0.00771 (13) |
C10 | 0.0279 (2) | 0.02365 (18) | 0.02265 (17) | −0.00918 (16) | −0.00444 (15) | 0.00971 (15) |
C11 | 0.01902 (14) | 0.01441 (13) | 0.01855 (14) | −0.00271 (11) | −0.00502 (11) | 0.00157 (11) |
C12 | 0.01007 (10) | 0.01462 (12) | 0.00949 (9) | −0.00024 (9) | −0.00037 (8) | 0.00007 (9) |
C13 | 0.01087 (12) | 0.0357 (2) | 0.01444 (12) | 0.00149 (13) | 0.00138 (10) | −0.00690 (13) |
C14 | 0.0348 (2) | 0.01510 (15) | 0.0288 (2) | 0.00187 (15) | −0.01295 (18) | −0.00410 (14) |
C15 | 0.01171 (11) | 0.01966 (14) | 0.00937 (10) | −0.00203 (10) | −0.00095 (8) | −0.00060 (9) |
C16 | 0.01053 (11) | 0.02037 (14) | 0.01038 (10) | −0.00063 (10) | −0.00057 (8) | −0.00215 (10) |
C17 | 0.01051 (11) | 0.01601 (12) | 0.01026 (10) | 0.00054 (9) | −0.00144 (8) | −0.00188 (9) |
C18 | 0.01103 (11) | 0.01612 (12) | 0.01470 (12) | 0.00068 (10) | −0.00351 (9) | −0.00152 (10) |
C19 | 0.01966 (15) | 0.0329 (2) | 0.01171 (12) | 0.00331 (15) | −0.00172 (11) | 0.00171 (13) |
C20 | 0.01336 (12) | 0.01910 (14) | 0.01171 (11) | 0.00028 (10) | −0.00047 (9) | −0.00231 (10) |
H1 | 0.036 (3) | 0.037938 | 0.031906 | 0.000943 | −0.012702 | −0.003791 |
H2 | 0.0239 (18) | 0.042959 | 0.024794 | 0.004722 | 0.003704 | −0.000933 |
H4A | 0.045 (2) | 0.033717 | 0.020681 | −0.009798 | −0.002633 | 0.00357 |
H4B | 0.044 (2) | 0.032753 | 0.03713 | 0.006089 | −0.000797 | −0.007312 |
H5A | 0.041 (3) | 0.05052 | 0.032291 | −0.008906 | −0.003872 | −0.000056 |
H5B | 0.041 (3) | 0.025801 | 0.039176 | −0.008683 | −0.017513 | 0.002455 |
H6 | 0.039 (2) | 0.041947 | 0.031583 | 0.011764 | −0.005939 | −0.00971 |
H7A | 0.041 (3) | 0.063346 | 0.024041 | −0.00895 | 0.004575 | −0.002998 |
H7B | 0.046 (3) | 0.033221 | 0.040528 | 0.003003 | −0.011436 | 0.002162 |
H8A | 0.047 (3) | 0.066511 | 0.024862 | −0.008165 | −0.003613 | −0.011166 |
H8B | 0.040 (2) | 0.088197 | 0.029493 | 0.009261 | 0.002724 | 0.000232 |
H8C | 0.044 (3) | 0.051412 | 0.031041 | 0.001998 | 0.006001 | 0.010057 |
H9A | 0.043 (3) | 0.034954 | 0.041101 | 0.004391 | −0.002587 | 0.000495 |
H9B | 0.046 (3) | 0.049161 | 0.022336 | −0.010495 | −0.003681 | 0.011898 |
H10A | 0.053 (3) | 0.032155 | 0.041403 | −0.012775 | −0.014012 | 0.01483 |
H10B | 0.042 (2) | 0.06066 | 0.030858 | −0.007366 | 0.001229 | 0.007901 |
H12 | 0.0235 (18) | 0.034612 | 0.023605 | 0.004005 | 0.005693 | −0.001971 |
H13A | 0.043 (3) | 0.056539 | 0.042862 | −0.010848 | 0.002448 | −0.013045 |
H13B | 0.063 (4) | 0.036556 | 0.044678 | 0.012038 | 0.007259 | 0.00392 |
H13C | 0.055 (3) | 0.065048 | 0.018415 | 0.00593 | 0.000263 | −0.00271 |
H14A | 0.047 (3) | 0.03841 | 0.028059 | 0.004601 | −0.006228 | −0.00104 |
H14B | 0.054 (3) | 0.020679 | 0.053591 | 0.000795 | −0.017341 | 0.006636 |
H15A | 0.032 (2) | 0.041149 | 0.023547 | 0.00313 | 0.005656 | −0.004656 |
H15B | 0.031 (2) | 0.019396 | 0.029532 | −0.001527 | −0.004132 | 0.001198 |
H16 | 0.027 (2) | 0.04299 | 0.024926 | −0.002 | 0.006203 | −0.002547 |
H19A | 0.046 (3) | 0.056019 | 0.024349 | 0.000658 | 0.001705 | −0.013764 |
H19B | 0.051 (3) | 0.033438 | 0.034216 | −0.003401 | −0.005926 | 0.005147 |
H20 | 0.036 (2) | 0.044209 | 0.025818 | −0.014326 | 0.002363 | −0.00119 |
H21 | 0.024 (2) | 0.053682 | 0.029362 | 0.007351 | −0.004264 | −0.014171 |
H22 | 0.030 (2) | 0.049454 | 0.026066 | 0.003983 | −0.005713 | 0.005198 |
O1—H1 | 0.9673 (13) | C10—C11 | 1.5065 (6) |
O2—H22 | 0.9667 (13) | C10—H10A | 1.092 (2) |
O3—C18 | 1.3438 (5) | C10—H10B | 1.0938 (10) |
O4—C20 | 1.4245 (5) | C11—C12 | 1.5092 (5) |
O4—H21 | 0.9667 (4) | C11—C14 | 1.3389 (7) |
O5—C18 | 1.2194 (5) | C12—C15 | 1.5374 (4) |
C2—C9 | 1.5360 (6) | C12—H12 | 1.0994 (9) |
C2—H2 | 1.0993 (8) | C13—H13A | 1.0583 (12) |
C3—C13 | 1.5341 (5) | C13—H13B | 1.061 (2) |
C4—C5 | 1.5280 (5) | C13—H13C | 1.0582 (4) |
C4—H4A | 1.0932 (6) | C14—H14A | 1.0763 (7) |
C4—H4B | 1.0915 (8) | C14—H14B | 1.076 (2) |
C5—C6 | 1.5170 (6) | C15—C16 | 1.4960 (5) |
C5—H5A | 1.0928 (8) | C15—H15A | 1.0922 (8) |
C5—H5B | 1.091 (2) | C15—H15B | 1.092 (2) |
C6—H6 | 1.1005 (8) | C16—C17 | 1.3390 (4) |
C7—H7A | 1.0912 (5) | C16—H16 | 1.0776 (4) |
C7—H7B | 1.094 (2) | C17—C18 | 1.4747 (4) |
C8—H8A | 1.0585 (14) | C17—C20 | 1.5065 (5) |
C8—H8B | 1.0603 (6) | C19—C20 | 1.5307 (5) |
C8—H8C | 1.060 (2) | C19—H19A | 1.0913 (12) |
C9—C10 | 1.5372 (6) | C19—H19B | 1.094 (2) |
C9—H9A | 1.0929 (10) | C20—H20 | 1.0997 (17) |
C9—H9B | 1.0921 (6) | ||
C20—O4—H21 | 106.64 (12) | C3—C13—H13A | 113.39 (8) |
C9—C2—H2 | 106.09 (11) | C3—C13—H13B | 112.09 (4) |
C5—C4—H4A | 112.14 (8) | C3—C13—H13C | 108.18 (5) |
C5—C4—H4B | 106.76 (8) | H13A—C13—H13B | 105.65 (7) |
H4A—C4—H4B | 111.74 (8) | H13A—C13—H13C | 108.56 (10) |
C4—C5—C6 | 111.03 (4) | H13B—C13—H13C | 108.83 (15) |
C4—C5—H5A | 111.64 (8) | C11—C14—H14A | 127.54 (12) |
C4—C5—H5B | 110.56 (4) | C11—C14—H14B | 120.19 (6) |
C6—C5—H5A | 109.00 (5) | H14A—C14—H14B | 112.18 (15) |
C6—C5—H5B | 112.25 (4) | C12—C15—C16 | 112.54 (3) |
H5A—C5—H5B | 102.05 (11) | C12—C15—H15A | 116.27 (6) |
C5—C6—H6 | 107.01 (5) | C12—C15—H15B | 106.87 (3) |
H7A—C7—H7B | 104.92 (13) | C16—C15—H15A | 107.56 (6) |
H8A—C8—H8B | 110.50 (13) | C16—C15—H15B | 106.36 (3) |
H8A—C8—H8C | 107.87 (7) | H15A—C15—H15B | 106.65 (11) |
H8B—C8—H8C | 101.37 (12) | C15—C16—C17 | 125.95 (3) |
C2—C9—C10 | 110.87 (3) | C15—C16—H16 | 116.61 (5) |
C2—C9—H9A | 106.57 (11) | C17—C16—H16 | 116.93 (4) |
C2—C9—H9B | 110.92 (12) | C16—C17—C18 | 122.04 (3) |
C10—C9—H9A | 111.97 (8) | C16—C17—C20 | 130.30 (3) |
C10—C9—H9B | 110.67 (7) | C18—C17—C20 | 107.65 (3) |
H9A—C9—H9B | 105.67 (9) | O3—C18—O5 | 121.46 (3) |
C9—C10—C11 | 110.59 (4) | O3—C18—C17 | 109.49 (3) |
C9—C10—H10A | 111.09 (4) | O5—C18—C17 | 129.04 (3) |
C9—C10—H10B | 108.82 (8) | C20—C19—H19A | 109.98 (5) |
C11—C10—H10A | 108.42 (5) | C20—C19—H19B | 113.51 (5) |
C11—C10—H10B | 105.78 (5) | H19A—C19—H19B | 109.92 (8) |
H10A—C10—H10B | 112.03 (11) | O4—C20—C17 | 111.71 (3) |
C10—C11—C12 | 113.29 (4) | O4—C20—C19 | 109.20 (3) |
C10—C11—C14 | 122.57 (4) | O4—C20—H20 | 110.59 (8) |
C12—C11—C14 | 124.06 (4) | C17—C20—C19 | 100.85 (3) |
C11—C12—C15 | 113.71 (3) | C17—C20—H20 | 115.95 (5) |
C11—C12—H12 | 107.52 (11) | C19—C20—H20 | 107.89 (5) |
C15—C12—H12 | 108.88 (5) | ||
H21—O4—C20—C17 | 95.14 (14) | C14—C11—C12—H12 | −132.38 (17) |
H21—O4—C20—C19 | −154.18 (15) | C12—C11—C14—H14A | −0.31 (12) |
H21—O4—C20—H20 | −35.59 (11) | C12—C11—C14—H14B | −176.6 (2) |
H2—C2—C9—C10 | −55.14 (11) | C11—C12—C15—C16 | −62.33 (12) |
H2—C2—C9—H9A | −177.23 (14) | C11—C12—C15—H15A | 62.35 (13) |
H2—C2—C9—H9B | 68.23 (12) | C11—C12—C15—H15B | −178.73 (15) |
H4A—C4—C5—C6 | 179.31 (16) | H12—C12—C15—C16 | 57.52 (12) |
H4A—C4—C5—H5A | 57.45 (12) | H12—C12—C15—H15A | −177.79 (16) |
H4A—C4—C5—H5B | −55.42 (12) | H12—C12—C15—H15B | −58.88 (11) |
H4B—C4—C5—C6 | −58.00 (12) | C12—C15—C16—C17 | 157.67 (18) |
H4B—C4—C5—H5A | −179.86 (15) | C12—C15—C16—H16 | −30.80 (11) |
H4B—C4—C5—H5B | 67.27 (12) | H15A—C15—C16—C17 | 28.33 (13) |
C4—C5—C6—H6 | 60.55 (12) | H15A—C15—C16—H16 | −160.14 (16) |
H5A—C5—C6—H6 | −176.06 (15) | H15B—C15—C16—C17 | −85.63 (15) |
H5B—C5—C6—H6 | −63.76 (12) | H15B—C15—C16—H16 | 85.90 (13) |
C2—C9—C10—C11 | −53.71 (12) | C15—C16—C17—C18 | 175.5 (2) |
C2—C9—C10—H10A | −174.15 (15) | C15—C16—C17—C20 | −3.54 (13) |
C2—C9—C10—H10B | 62.07 (12) | H16—C16—C17—C18 | 3.97 (11) |
H9A—C9—C10—C11 | 65.16 (12) | H16—C16—C17—C20 | −175.0 (2) |
H9A—C9—C10—H10A | −55.28 (12) | C16—C17—C18—O3 | −169.51 (18) |
H9A—C9—C10—H10B | −179.06 (16) | C16—C17—C18—O5 | 11.47 (15) |
H9B—C9—C10—C11 | −177.24 (15) | C16—C17—C20—O4 | −84.69 (17) |
H9B—C9—C10—H10A | 62.33 (12) | C16—C17—C20—C19 | 159.41 (18) |
H9B—C9—C10—H10B | −61.46 (12) | C16—C17—C20—H20 | 43.24 (14) |
C9—C10—C11—C12 | 56.16 (12) | C20—C17—C18—O3 | 9.70 (11) |
C9—C10—C11—C14 | −120.59 (17) | C18—C17—C20—O4 | 96.19 (13) |
H10A—C10—C11—C12 | 178.17 (15) | C20—C17—C18—O5 | −169.3 (2) |
H10A—C10—C11—C14 | 1.42 (12) | C18—C17—C20—C19 | −19.71 (10) |
H10B—C10—C11—C12 | −61.51 (12) | C18—C17—C20—H20 | −135.88 (15) |
H10B—C10—C11—C14 | 121.74 (17) | H19A—C19—C20—O4 | 24.38 (11) |
C10—C11—C12—C15 | 171.54 (16) | H19A—C19—C20—C17 | 142.12 (13) |
C10—C11—C12—H12 | 50.92 (11) | H19A—C19—C20—H20 | −95.87 (13) |
C10—C11—C14—H14A | 176.1 (2) | H19B—C19—C20—O4 | 147.99 (15) |
C10—C11—C14—H14B | −0.17 (12) | H19B—C19—C20—C17 | −94.27 (13) |
C14—C11—C12—C15 | −11.76 (13) | H19B—C19—C20—H20 | 27.74 (11) |