Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S010827019901358X/ja1004sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S010827019901358X/ja1004Isup2.hkl |
CCDC reference: 142750
As might be expected from the above, data were limited in scope and intensity, nonetheless permitting solution of the structure, with stable and meaningful refinement of non-H-atom anisotropic displacement parameters and (x, y, z, Uiso)H, the latter permitting delineation of any hydrogen-bonding interactions, particularly of the hydroxyl H atoms (Hn3 and Hn4'); for Hn3, none are discernible but those of Hn4' are of interest, being directed toward On5' [H···O 2.08 (5) and 2.24 (4) Å (n = 1,2)], with further interactions being intermolecular [H14'···O24(x − 1, y, z) 2.11 (7) and H24'···O14 1 + x, y − 1,z) 2.33 (5) Å] to the lactone carbonyl O atoms. The usual exocyclic angular distortions are found at the points of fusion of the methoxy and hydroxy substituents to the pendant aromatic ring.
Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT; program(s) used to solve structure: Xtal3.5 GENTAN (Hall et al., 1995); program(s) used to refine structure: Xtal3.5 CRYLSQ; molecular graphics: Xtal3.5 PIG and ORTEP; software used to prepare material for publication: Xtal3.5 BONDLA and CIFIO.
C21H20O8 | V = 926.8 (2) Å3 |
Mr = 400.38 | Z = 2 |
Triclinic, P1 | Dx = 1.435 Mg m−3 |
Hall symbol: p 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.854 (1) Å | Cell parameters from 1868 reflections |
b = 9.384 (1) Å | θ = 2–29° |
c = 13.230 (2) Å | µ = 0.11 mm−1 |
α = 101.563 (2)° | T = 300 K |
β = 103.699 (2)° | Plate, colourless |
γ = 90.184 (2)° | 0.20 × 0.10 × 0.05 mm |
Bruker SMART CCD diffractometer | Rint = 0.068 |
ω scans | θmax = 28.4°, θmin = 1.6° |
10605 measured reflections | h = −10→10 |
4460 independent reflections | k = −12→12 |
2592 reflections with F2 > 2σF2 | l = −18→18 |
Refinement on F2 | 4163.51 constraints |
Least-squares matrix: full | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.040 | Weighting scheme based on measured s.u.'s |
wR(F2) = 0.044 | (Δ/σ)max = 0.02 |
S = 1.07 | Δρmax = 0.20 e Å−3 |
4460 reflections | Δρmin = −0.18 e Å−3 |
681 parameters | Extinction correction: Zachariasen |
3941.12 restraints | Extinction coefficient: 2063.4 (7) |
C21H20O8 | γ = 90.184 (2)° |
Mr = 400.38 | V = 926.8 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.854 (1) Å | Mo Kα radiation |
b = 9.384 (1) Å | µ = 0.11 mm−1 |
c = 13.230 (2) Å | T = 300 K |
α = 101.563 (2)° | 0.20 × 0.10 × 0.05 mm |
β = 103.699 (2)° |
Bruker SMART CCD diffractometer | 2592 reflections with F2 > 2σF2 |
10605 measured reflections | Rint = 0.068 |
4460 independent reflections |
R[F2 > 2σ(F2)] = 0.040 | 3941.12 restraints |
wR(F2) = 0.044 | All H-atom parameters refined |
S = 1.07 | Δρmax = 0.20 e Å−3 |
4460 reflections | Δρmin = −0.18 e Å−3 |
681 parameters |
x | y | z | Uiso*/Ueq | ||
C11 | 0.00000 | 0.50000 | 0.00000 | 0.0332 (17) | |
C12 | −0.1608 (6) | 0.5670 (5) | 0.0330 (4) | 0.0319 (17) | |
C11' | −0.1443 (6) | 0.5769 (5) | 0.1521 (3) | 0.0319 (16) | |
C12' | 0.0113 (6) | 0.6204 (5) | 0.2275 (4) | 0.0373 (18) | |
C13' | 0.0275 (6) | 0.6217 (5) | 0.3340 (3) | 0.0354 (17) | |
O13' | 0.1786 (5) | 0.6592 (4) | 0.4120 (3) | 0.0603 (15) | |
C131' | 0.3026 (7) | 0.7542 (6) | 0.3935 (4) | 0.054 (2) | |
C14' | −0.1164 (6) | 0.5730 (5) | 0.3664 (4) | 0.0371 (17) | |
O14' | −0.0961 (5) | 0.5716 (5) | 0.4720 (3) | 0.0568 (16) | |
C15' | −0.2700 (6) | 0.5300 (5) | 0.2924 (4) | 0.0380 (18) | |
O15' | −0.4016 (5) | 0.4855 (5) | 0.3340 (3) | 0.0597 (15) | |
C151' | −0.5537 (7) | 0.4118 (7) | 0.2605 (5) | 0.074 (3) | |
C16' | −0.2865 (6) | 0.5302 (5) | 0.1866 (4) | 0.0362 (19) | |
C13 | −0.1875 (6) | 0.7130 (5) | −0.0030 (3) | 0.0317 (16) | |
O13 | −0.2507 (5) | 0.6885 (4) | −0.1165 (3) | 0.0410 (13) | |
C14 | −0.3114 (6) | 0.8197 (5) | 0.0419 (3) | 0.038 (2) | |
O14 | −0.4438 (5) | 0.7960 (4) | 0.0690 (3) | 0.0566 (15) | |
O15 | −0.2573 (5) | 0.9572 (4) | 0.0424 (3) | 0.0464 (14) | |
C16 | −0.0896 (7) | 0.9531 (5) | 0.0081 (4) | 0.040 (2) | |
C17 | −0.0218 (6) | 0.8080 (5) | 0.0270 (4) | 0.0324 (17) | |
C18 | 0.1140 (7) | 0.7386 (5) | −0.0292 (4) | 0.0371 (19) | |
C19 | 0.1333 (5) | 0.5807 (5) | −0.0205 (3) | 0.0337 (17) | |
C110 | 0.2862 (6) | 0.5138 (5) | −0.0396 (4) | 0.038 (2) | |
C111 | 0.2960 (6) | 0.3694 (5) | −0.0414 (3) | 0.040 (2) | |
O111 | 0.4311 (5) | 0.2814 (5) | −0.0634 (3) | 0.0555 (15) | |
C112 | 0.1636 (7) | 0.2866 (5) | −0.0260 (4) | 0.040 (2) | |
O112 | 0.2049 (5) | 0.1430 (4) | −0.0375 (3) | 0.0629 (17) | |
C113 | 0.0177 (6) | 0.3480 (5) | −0.0023 (3) | 0.043 (2) | |
C114 | 0.3846 (8) | 0.1413 (6) | −0.0462 (5) | 0.062 (3) | |
C21 | 0.2539 (5) | 0.1847 (5) | 0.6569 (3) | 0.0335 (18) | |
C22 | 0.4146 (6) | 0.2327 (5) | 0.6215 (4) | 0.0313 (17) | |
C21' | 0.3969 (6) | 0.1735 (5) | 0.5033 (3) | 0.0338 (17) | |
C22' | 0.2419 (6) | 0.1754 (5) | 0.4276 (4) | 0.0359 (18) | |
C23' | 0.2253 (6) | 0.1179 (5) | 0.3214 (3) | 0.0364 (18) | |
O23' | 0.0757 (5) | 0.1117 (4) | 0.2434 (3) | 0.0544 (15) | |
C231' | −0.0490 (7) | 0.2179 (6) | 0.2600 (4) | 0.052 (2) | |
C24' | 0.3696 (6) | 0.0518 (5) | 0.2883 (4) | 0.0379 (18) | |
O24' | 0.3483 (6) | −0.0081 (5) | 0.1829 (3) | 0.0559 (18) | |
C25' | 0.5247 (6) | 0.0498 (5) | 0.3626 (4) | 0.0382 (19) | |
O25' | 0.6559 (5) | −0.0162 (5) | 0.3216 (3) | 0.0564 (15) | |
C251' | 0.8064 (8) | −0.0524 (7) | 0.3919 (5) | 0.075 (3) | |
C26' | 0.5398 (6) | 0.1094 (5) | 0.4693 (4) | 0.0363 (18) | |
C23 | 0.4421 (6) | 0.3984 (5) | 0.6569 (4) | 0.0341 (17) | |
O23 | 0.5183 (5) | 0.4348 (4) | 0.7714 (3) | 0.0390 (13) | |
C24 | 0.5678 (6) | 0.4783 (5) | 0.6132 (3) | 0.038 (2) | |
O24 | 0.6971 (5) | 0.4382 (4) | 0.5831 (3) | 0.0552 (15) | |
O25 | 0.5141 (5) | 0.6164 (4) | 0.6139 (3) | 0.0490 (14) | |
C26 | 0.3455 (7) | 0.6335 (5) | 0.6472 (4) | 0.044 (2) | |
C27 | 0.2761 (6) | 0.4774 (5) | 0.6285 (4) | 0.0328 (18) | |
C28 | 0.1397 (6) | 0.4424 (5) | 0.6838 (4) | 0.036 (2) | |
C29 | 0.1261 (6) | 0.2796 (5) | 0.6814 (4) | 0.0336 (17) | |
C210 | −0.0229 (6) | 0.2251 (6) | 0.7060 (4) | 0.043 (2) | |
C211 | −0.0387 (6) | 0.0819 (6) | 0.7055 (4) | 0.044 (2) | |
O211 | −0.1730 (5) | 0.0048 (5) | 0.7270 (3) | 0.0616 (16) | |
C212 | 0.0908 (7) | −0.0112 (6) | 0.6841 (4) | 0.044 (2) | |
O212 | 0.0460 (6) | −0.1506 (5) | 0.6928 (3) | 0.0652 (16) | |
C213 | 0.2352 (6) | 0.0362 (5) | 0.6578 (3) | 0.043 (2) | |
C214 | −0.1379 (7) | −0.1454 (6) | 0.6938 (5) | 0.063 (3) | |
H12 | −0.273 (4) | 0.505 (3) | −0.005 (2) | 0.030 (8)* | |
H12' | 0.106 (4) | 0.645 (3) | 0.207 (2) | 0.023 (8)* | |
H131'a | 0.277 (7) | 0.863 (6) | 0.433 (5) | 0.18 (3)* | |
H131'b | 0.406 (5) | 0.763 (4) | 0.454 (3) | 0.068 (12)* | |
H131'c | 0.364 (5) | 0.708 (4) | 0.330 (3) | 0.098 (15)* | |
H14' | −0.201 (8) | 0.525 (6) | 0.473 (5) | 0.20 (3)* | |
H151'a | −0.630 (5) | 0.377 (4) | 0.305 (3) | 0.068 (11)* | |
H151'b | −0.613 (6) | 0.483 (5) | 0.219 (4) | 0.101 (17)* | |
H151'c | −0.486 (5) | 0.313 (4) | 0.221 (3) | 0.091 (14)* | |
H16' | −0.366 (4) | 0.496 (3) | 0.144 (3) | 0.037 (11)* | |
H13 | −0.319 (4) | 0.608 (3) | −0.138 (2) | 0.037 (10)* | |
H16a | −0.017 (4) | 1.046 (3) | 0.052 (2) | 0.029 (8)* | |
H16b | −0.125 (3) | 0.961 (3) | −0.074 (2) | 0.027 (8)* | |
H17 | 0.023 (3) | 0.820 (2) | 0.104 (2) | 0.013 (7)* | |
H18a | 0.069 (4) | 0.733 (3) | −0.116 (2) | 0.048 (9)* | |
H18b | 0.219 (4) | 0.790 (3) | −0.000 (2) | 0.048 (11)* | |
H110 | 0.377 (4) | 0.569 (3) | −0.049 (2) | 0.038 (10)* | |
H113 | −0.093 (5) | 0.282 (4) | 0.015 (3) | 0.084 (13)* | |
H114a | 0.395 (6) | 0.073 (5) | −0.096 (4) | 0.10 (2)* | |
H114b | 0.478 (6) | 0.125 (4) | 0.031 (4) | 0.111 (16)* | |
H22 | 0.509 (4) | 0.183 (3) | 0.652 (2) | 0.046 (10)* | |
H22' | 0.159 (3) | 0.209 (3) | 0.451 (2) | 0.012 (8)* | |
H231'a | −0.128 (5) | 0.201 (4) | 0.191 (3) | 0.077 (14)* | |
H231'b | −0.078 (5) | 0.205 (4) | 0.335 (4) | 0.107 (16)* | |
H231'c | −0.004 (5) | 0.323 (4) | 0.286 (3) | 0.082 (14)* | |
H24' | 0.431 (5) | −0.032 (5) | 0.179 (4) | 0.08 (2)* | |
H251'a | 0.760 (6) | −0.111 (5) | 0.434 (4) | 0.12 (2)* | |
H251'b | 0.921 (7) | −0.081 (5) | 0.358 (4) | 0.14 (2)* | |
H251'c | 0.856 (5) | 0.038 (4) | 0.442 (3) | 0.051 (12)* | |
H26' | 0.643 (3) | 0.102 (3) | 0.520 (2) | 0.024 (8)* | |
H23 | 0.486 (6) | 0.368 (5) | 0.795 (4) | 0.12 (2)* | |
H26a | 0.277 (4) | 0.701 (4) | 0.605 (3) | 0.066 (12)* | |
H26b | 0.380 (3) | 0.688 (3) | 0.726 (2) | 0.032 (8)* | |
H27 | 0.234 (3) | 0.446 (3) | 0.552 (2) | 0.029 (8)* | |
H28a | 0.169 (4) | 0.490 (3) | 0.761 (2) | 0.049 (10)* | |
H28b | 0.014 (4) | 0.473 (3) | 0.654 (2) | 0.040 (9)* | |
H210 | −0.103 (4) | 0.283 (3) | 0.718 (2) | 0.021 (9)* | |
H213 | 0.328 (4) | −0.031 (4) | 0.643 (3) | 0.051 (11)* | |
H214a | −0.196 (4) | −0.180 (4) | 0.608 (3) | 0.068 (12)* | |
H214b | −0.162 (5) | −0.201 (4) | 0.747 (3) | 0.084 (14)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C11 | 0.032 (2) | 0.038 (2) | 0.029 (2) | 0.0022 (18) | 0.0098 (16) | 0.0084 (16) |
C12 | 0.029 (2) | 0.031 (2) | 0.035 (2) | −0.0010 (17) | 0.0050 (16) | 0.0042 (15) |
C11' | 0.035 (2) | 0.031 (2) | 0.030 (2) | 0.0037 (16) | 0.0091 (16) | 0.0065 (15) |
C12' | 0.031 (2) | 0.041 (2) | 0.041 (2) | −0.0022 (18) | 0.0122 (18) | 0.0144 (17) |
C13' | 0.037 (2) | 0.038 (2) | 0.032 (2) | −0.0045 (17) | 0.0029 (17) | 0.0101 (16) |
O13' | 0.0515 (17) | 0.084 (2) | 0.0453 (17) | −0.0275 (15) | −0.0043 (13) | 0.0290 (14) |
C131' | 0.045 (3) | 0.068 (3) | 0.049 (3) | −0.018 (2) | 0.003 (2) | 0.012 (2) |
C14' | 0.043 (2) | 0.037 (2) | 0.032 (2) | 0.0022 (17) | 0.0134 (18) | 0.0119 (16) |
O14' | 0.0553 (19) | 0.076 (2) | 0.0386 (17) | −0.0100 (16) | 0.0102 (13) | 0.0185 (13) |
C15' | 0.034 (2) | 0.043 (2) | 0.037 (2) | −0.0004 (18) | 0.0120 (18) | 0.0138 (17) |
O15' | 0.0363 (16) | 0.092 (2) | 0.0510 (16) | −0.0089 (15) | 0.0150 (13) | 0.0252 (15) |
C151' | 0.054 (3) | 0.086 (4) | 0.082 (4) | −0.013 (3) | 0.032 (3) | 0.027 (3) |
C16' | 0.026 (2) | 0.044 (2) | 0.039 (2) | −0.0030 (18) | 0.0048 (19) | 0.0087 (18) |
C13 | 0.032 (2) | 0.034 (2) | 0.030 (2) | 0.0000 (16) | 0.0067 (15) | 0.0048 (15) |
O13 | 0.0506 (16) | 0.0375 (16) | 0.0349 (15) | −0.0089 (13) | −0.0001 (12) | 0.0078 (12) |
C14 | 0.037 (2) | 0.042 (3) | 0.035 (2) | 0.008 (2) | −0.0001 (17) | 0.0042 (17) |
O14 | 0.0386 (16) | 0.0534 (18) | 0.078 (2) | 0.0075 (13) | 0.0245 (15) | 0.0112 (14) |
O15 | 0.0444 (17) | 0.0318 (16) | 0.0631 (18) | 0.0032 (13) | 0.0127 (13) | 0.0059 (12) |
C16 | 0.046 (3) | 0.035 (2) | 0.040 (2) | −0.0035 (19) | 0.008 (2) | 0.0083 (17) |
C17 | 0.034 (2) | 0.029 (2) | 0.035 (2) | −0.0028 (16) | 0.0065 (17) | 0.0066 (15) |
C18 | 0.035 (2) | 0.030 (2) | 0.046 (2) | −0.0059 (18) | 0.0122 (18) | 0.0074 (16) |
C19 | 0.037 (2) | 0.037 (2) | 0.0268 (19) | −0.0030 (17) | 0.0067 (16) | 0.0043 (15) |
C110 | 0.033 (2) | 0.044 (3) | 0.035 (2) | −0.004 (2) | 0.0108 (17) | 0.0055 (17) |
C111 | 0.038 (2) | 0.049 (3) | 0.032 (2) | 0.011 (2) | 0.0087 (17) | 0.0072 (17) |
O111 | 0.0458 (16) | 0.0507 (18) | 0.0700 (19) | 0.0144 (14) | 0.0228 (14) | 0.0103 (14) |
C112 | 0.043 (2) | 0.037 (2) | 0.040 (2) | 0.009 (2) | 0.0123 (18) | 0.0125 (17) |
O112 | 0.061 (2) | 0.0408 (18) | 0.087 (2) | 0.0134 (14) | 0.0314 (17) | 0.0200 (14) |
C113 | 0.050 (3) | 0.039 (2) | 0.039 (2) | −0.001 (2) | 0.0089 (18) | 0.0157 (17) |
C114 | 0.063 (3) | 0.049 (3) | 0.075 (3) | 0.021 (3) | 0.025 (3) | 0.017 (3) |
C21 | 0.032 (2) | 0.041 (2) | 0.027 (2) | −0.0072 (18) | 0.0073 (16) | 0.0034 (16) |
C22 | 0.029 (2) | 0.029 (2) | 0.036 (2) | −0.0007 (17) | 0.0038 (16) | 0.0072 (16) |
C21' | 0.036 (2) | 0.034 (2) | 0.032 (2) | −0.0050 (17) | 0.0118 (16) | 0.0059 (15) |
C22' | 0.027 (2) | 0.036 (2) | 0.044 (2) | 0.0045 (18) | 0.014 (2) | −0.0001 (17) |
C23' | 0.037 (2) | 0.037 (2) | 0.035 (2) | 0.0052 (18) | 0.0020 (18) | 0.0042 (17) |
O23' | 0.0500 (17) | 0.071 (2) | 0.0427 (16) | 0.0235 (15) | −0.0075 (13) | −0.0112 (12) |
C231' | 0.056 (3) | 0.055 (3) | 0.046 (3) | 0.019 (2) | −0.002 (2) | 0.000 (2) |
C24' | 0.045 (2) | 0.036 (2) | 0.032 (2) | −0.0013 (18) | 0.0088 (18) | 0.0016 (16) |
O24' | 0.055 (2) | 0.072 (2) | 0.0401 (19) | 0.0159 (18) | 0.0109 (15) | −0.0023 (13) |
C25' | 0.033 (2) | 0.038 (2) | 0.043 (2) | 0.0014 (17) | 0.0157 (19) | 0.0044 (17) |
O25' | 0.0403 (16) | 0.080 (2) | 0.0488 (17) | 0.0125 (15) | 0.0125 (13) | −0.0013 (14) |
C251' | 0.052 (3) | 0.080 (4) | 0.091 (4) | 0.025 (3) | 0.026 (3) | 0.020 (3) |
C26' | 0.028 (2) | 0.043 (2) | 0.038 (2) | 0.0023 (17) | 0.0057 (18) | 0.0064 (17) |
C23 | 0.034 (2) | 0.038 (2) | 0.031 (2) | −0.0048 (17) | 0.0077 (16) | 0.0073 (15) |
O23 | 0.0436 (15) | 0.0419 (16) | 0.0314 (14) | −0.0079 (12) | 0.0034 (11) | 0.0051 (11) |
C24 | 0.040 (2) | 0.043 (3) | 0.030 (2) | −0.011 (2) | −0.0031 (17) | 0.0100 (17) |
O24 | 0.0368 (16) | 0.064 (2) | 0.0648 (19) | −0.0029 (14) | 0.0218 (14) | 0.0206 (14) |
O25 | 0.0479 (16) | 0.0387 (17) | 0.0603 (18) | −0.0063 (13) | 0.0155 (13) | 0.0157 (13) |
C26 | 0.049 (3) | 0.038 (2) | 0.044 (3) | −0.000 (2) | 0.008 (2) | 0.008 (2) |
C27 | 0.036 (2) | 0.030 (2) | 0.032 (2) | −0.0062 (16) | 0.0027 (17) | 0.0074 (16) |
C28 | 0.035 (2) | 0.037 (2) | 0.037 (2) | 0.0026 (18) | 0.0065 (18) | 0.0080 (17) |
C29 | 0.033 (2) | 0.038 (2) | 0.030 (2) | −0.0019 (18) | 0.0018 (16) | 0.0096 (15) |
C210 | 0.031 (2) | 0.050 (3) | 0.048 (2) | 0.007 (2) | 0.0127 (19) | 0.015 (2) |
C211 | 0.041 (2) | 0.055 (3) | 0.036 (2) | −0.011 (2) | 0.0089 (18) | 0.0150 (19) |
O211 | 0.0467 (17) | 0.068 (2) | 0.070 (2) | −0.0152 (15) | 0.0201 (14) | 0.0235 (15) |
C212 | 0.055 (3) | 0.039 (2) | 0.037 (2) | −0.013 (2) | 0.009 (2) | 0.0074 (17) |
O212 | 0.073 (2) | 0.0416 (17) | 0.081 (2) | −0.0120 (14) | 0.0276 (17) | 0.0180 (14) |
C213 | 0.047 (2) | 0.035 (2) | 0.047 (2) | −0.000 (2) | 0.019 (2) | 0.0076 (17) |
C214 | 0.067 (3) | 0.055 (3) | 0.067 (3) | −0.025 (2) | 0.011 (3) | 0.019 (2) |
C11—C12 | 1.529 (5) | C21—C22 | 1.542 (7) |
C11—C19 | 1.399 (5) | C21—C29 | 1.396 (7) |
C11—C113 | 1.429 (5) | C21—C213 | 1.403 (7) |
C12—C11' | 1.534 (6) | C22—C21' | 1.523 (6) |
C12—C13 | 1.537 (7) | C22—C23 | 1.531 (6) |
C12—H12 | 1.02 (3) | C22—H22 | 0.93 (3) |
C11'—C12' | 1.383 (6) | C21'—C22' | 1.384 (6) |
C11'—C16' | 1.402 (8) | C21'—C26' | 1.400 (7) |
C12'—C13' | 1.382 (7) | C22'—C23' | 1.376 (6) |
C12'—H12' | 0.89 (3) | C22'—H22' | 0.82 (3) |
C13'—O13' | 1.367 (5) | C23'—O23' | 1.360 (5) |
C13'—C14' | 1.405 (7) | C23'—C24' | 1.411 (7) |
O13'—C131' | 1.413 (8) | O23'—C231' | 1.421 (7) |
C131'—H131'a | 1.09 (6) | C231'—H231'a | 0.95 (4) |
C131'—H131'b | 0.98 (3) | C231'—H231'b | 1.10 (5) |
C131'—H131'c | 1.08 (5) | C231'—H231'c | 1.01 (4) |
C14'—O14' | 1.370 (6) | C24'—O24' | 1.364 (6) |
C14'—C15' | 1.362 (6) | C24'—C25' | 1.376 (6) |
O14'—H14' | 0.94 (6) | O24'—H24' | 0.70 (4) |
C15'—O15' | 1.381 (7) | C25'—O25' | 1.369 (7) |
C15'—C16' | 1.375 (7) | C25'—C26' | 1.387 (7) |
O15'—C151' | 1.424 (6) | O25'—C251' | 1.409 (7) |
C151'—H151'a | 1.02 (4) | C251'—H251'a | 0.98 (6) |
C151'—H151'b | 1.00 (5) | C251'—H251'b | 1.11 (6) |
C151'—H151'c | 1.16 (4) | C251'—H251'c | 0.98 (3) |
C16'—H16' | 0.76 (3) | C26'—H26' | 0.93 (3) |
C13—O13 | 1.436 (6) | C23—O23 | 1.460 (6) |
C13—C14 | 1.531 (7) | C23—C24 | 1.520 (8) |
C13—C17 | 1.501 (6) | C23—C27 | 1.509 (6) |
O13—H13 | 0.88 (3) | O23—H23 | 0.82 (5) |
C14—O14 | 1.211 (7) | C24—O24 | 1.211 (7) |
C14—O15 | 1.355 (6) | C24—O25 | 1.363 (6) |
O15—C16 | 1.490 (7) | O25—C26 | 1.491 (7) |
C16—C17 | 1.509 (7) | C26—C27 | 1.513 (7) |
C16—H16a | 1.03 (3) | C26—H26a | 1.00 (4) |
C16—H16b | 1.07 (3) | C26—H26b | 1.03 (3) |
C17—C18 | 1.517 (7) | C27—C28 | 1.501 (8) |
C17—H17 | 0.98 (3) | C27—H27 | 0.97 (3) |
C18—C19 | 1.514 (7) | C28—C29 | 1.525 (7) |
C18—H18a | 1.11 (3) | C28—H28a | 1.00 (3) |
C18—H18b | 0.92 (3) | C28—H28b | 1.03 (3) |
C19—C110 | 1.409 (7) | C29—C210 | 1.407 (7) |
C110—C111 | 1.353 (7) | C210—C211 | 1.347 (8) |
C110—H110 | 0.93 (3) | C210—H210 | 0.86 (3) |
C111—O111 | 1.396 (6) | C211—O211 | 1.392 (7) |
C111—C112 | 1.374 (7) | C211—C212 | 1.386 (7) |
O111—C114 | 1.439 (8) | O211—C214 | 1.438 (7) |
C112—O112 | 1.374 (6) | C212—O212 | 1.387 (7) |
C112—C113 | 1.358 (7) | C212—C213 | 1.361 (8) |
O112—C114 | 1.443 (8) | O212—C214 | 1.448 (8) |
C113—H113 | 1.16 (4) | C213—H213 | 0.99 (3) |
C114—H114a | 0.84 (4) | C214—H214a | 1.09 (4) |
C114—H114b | 1.15 (4) | C214—H214b | 1.01 (4) |
C11···C11' | 2.522 (5) | C22···C213 | 2.504 (7) |
C11···C12' | 2.976 (5) | C22···H22' | 2.61 (2) |
C11···C13 | 2.487 (5) | C22···H26' | 2.65 (3) |
C11···O13 | 3.010 (4) | C22···H23 | 2.33 (5) |
C11···C17 | 2.851 (4) | C22···H27 | 2.65 (3) |
C11···C18 | 2.542 (5) | C22···H213 | 2.65 (4) |
C11···C110 | 2.435 (5) | C21'···C23' | 2.416 (6) |
C11···C111 | 2.750 (5) | C21'···C24' | 2.802 (6) |
C11···C112 | 2.393 (5) | C21'···C25' | 2.419 (7) |
C11···H12 | 2.13 (3) | C21'···C23 | 2.577 (6) |
C11···H113 | 2.23 (4) | C21'···H22 | 1.94 (3) |
C12···C12' | 2.557 (6) | C21'···H22' | 1.89 (3) |
C12···C16' | 2.541 (8) | C21'···H26' | 2.02 (3) |
C12···O13 | 2.440 (6) | C22'···O23' | 2.430 (6) |
C12···C14 | 2.647 (7) | C22'···C231' | 2.873 (7) |
C12···C17 | 2.532 (7) | C22'···C24' | 2.403 (7) |
C12···C19 | 2.581 (7) | C22'···C25' | 2.753 (7) |
C12···C113 | 2.520 (7) | C22'···C26' | 2.387 (7) |
C12···H12' | 2.70 (2) | C22'···H231'b | 2.57 (4) |
C12···H16' | 2.59 (4) | C23'···C231' | 2.381 (7) |
C12···H13 | 2.41 (3) | C23'···O24' | 2.379 (7) |
C12···H17 | 2.66 (2) | C23'···C25' | 2.404 (6) |
C11'···C13' | 2.417 (6) | C23'···C26' | 2.777 (6) |
C11'···C14' | 2.799 (7) | C23'···H22' | 1.94 (3) |
C11'···C15' | 2.409 (7) | C23'···H231'b | 2.56 (4) |
C11'···C13 | 2.584 (7) | C23'···H231'c | 2.68 (4) |
C11'···H12 | 2.05 (2) | O23'···C24' | 2.343 (6) |
C11'···H12' | 1.98 (3) | O23'···O24' | 2.637 (6) |
C11'···H16' | 1.87 (3) | O23'···H16a | 2.41 (3) |
C12'···O13' | 2.436 (6) | O23'···H22' | 2.63 (2) |
C12'···C131' | 2.851 (6) | O23'···H231'a | 1.86 (4) |
C12'···C14' | 2.404 (8) | O23'···H231'b | 1.99 (5) |
C12'···C15' | 2.741 (7) | O23'···H231'c | 2.09 (4) |
C12'···C16' | 2.385 (7) | C231'···H22' | 2.68 (2) |
C13'···C131' | 2.370 (7) | C24'···O25' | 2.305 (6) |
C13'···O14' | 2.382 (7) | C24'···C26' | 2.403 (6) |
C13'···C15' | 2.385 (6) | C24'···H24' | 1.68 (5) |
C13'···C16' | 2.768 (6) | O24'···C25' | 2.405 (6) |
C13'···H12' | 1.97 (3) | O24'···O25' | 2.677 (6) |
O13'···C14' | 2.349 (6) | O24'···H18b | 2.73 (3) |
O13'···O14' | 2.650 (6) | C25'···C251' | 2.391 (8) |
O13'···H12' | 2.61 (3) | C25'···H24' | 2.33 (5) |
O13'···H131'a | 2.00 (6) | C25'···H251'a | 2.52 (5) |
O13'···H131'b | 1.94 (4) | C25'···H251'c | 2.58 (3) |
O13'···H131'c | 2.11 (5) | C25'···H26' | 2.02 (3) |
O13'···H26a | 2.43 (3) | O25'···C26' | 2.443 (7) |
C131'···H12' | 2.58 (2) | O25'···H24' | 2.24 (4) |
C14'···O15' | 2.295 (6) | O25'···H251'a | 1.91 (5) |
C14'···C16' | 2.391 (6) | O25'···H251'b | 2.14 (5) |
C14'···H14' | 1.82 (7) | O25'···H251'c | 1.94 (3) |
C14'···H231'c | 2.62 (4) | O25'···H26' | 2.66 (3) |
O14'···C15' | 2.398 (6) | C251'···C26' | 2.855 (8) |
O14'···O15' | 2.657 (5) | C251'···H26' | 2.58 (3) |
O14'···O24 | 2.868 (7) | C26'···H22 | 2.45 (3) |
O14'···H28b | 2.71 (3) | C26'···H251'c | 2.66 (4) |
C15'···C151' | 2.393 (8) | C23···O24 | 2.484 (7) |
C15'···H14' | 2.33 (6) | C23···O25 | 2.332 (7) |
C15'···H151'b | 2.64 (4) | C23···C26 | 2.353 (7) |
C15'···H151'c | 2.52 (4) | C23···C28 | 2.507 (7) |
C15'···H16' | 1.89 (3) | C23···C29 | 2.832 (7) |
O15'···C16' | 2.441 (7) | C23···H22 | 2.08 (3) |
O15'···H131'c | 2.79 (4) | C23···H23 | 1.86 (5) |
O15'···H14' | 2.08 (5) | C23···H27 | 1.99 (3) |
O15'···H151'a | 1.97 (4) | O23···C24 | 2.329 (7) |
O15'···H151'b | 1.97 (4) | O23···O24 | 3.141 (6) |
O15'···H151'c | 1.96 (3) | O23···O25 | 2.939 (6) |
O15'···H16' | 2.62 (4) | O23···C26 | 2.865 (7) |
C151'···C16' | 2.826 (9) | O23···C27 | 2.441 (6) |
C151'···H16' | 2.60 (4) | O23···C28 | 2.931 (6) |
C16'···H12 | 2.52 (3) | O23···H13 | 2.05 (3) |
C13···O14 | 2.487 (6) | O23···H22 | 2.55 (3) |
C13···O15 | 2.351 (6) | O23···H26b | 2.73 (3) |
C13···C16 | 2.344 (7) | O23···H28a | 2.77 (3) |
C13···C18 | 2.491 (7) | C24···C26 | 2.344 (7) |
C13···C19 | 2.850 (6) | C24···C27 | 2.347 (7) |
C13···H12 | 2.06 (3) | C24···H27 | 2.55 (3) |
C13···H13 | 1.90 (3) | O24···O25 | 2.247 (6) |
C13···H17 | 2.02 (2) | O24···H14' | 2.11 (7) |
O13···C14 | 2.361 (6) | O24···H28b | 2.44 (3) |
O13···O14 | 3.181 (6) | O24···H210 | 2.73 (3) |
O13···O15 | 2.951 (5) | O25···C27 | 2.343 (6) |
O13···C16 | 2.800 (6) | O25···H131'b | 2.73 (4) |
O13···C17 | 2.369 (5) | O25···H26a | 2.01 (4) |
O13···C18 | 2.823 (6) | O25···H26b | 2.02 (3) |
O13···O23 | 2.905 (5) | O25···H27 | 2.58 (2) |
O13···H12 | 2.52 (3) | C26···C28 | 2.600 (8) |
O13···H16b | 2.64 (2) | C26···H27 | 2.01 (2) |
O13···H18a | 2.54 (3) | C27···C29 | 2.495 (7) |
O13···H214b | 2.48 (4) | C27···H26a | 2.18 (4) |
C14···C16 | 2.320 (8) | C27···H26b | 2.16 (3) |
C14···C17 | 2.330 (7) | C27···H28a | 2.10 (4) |
C14···H17 | 2.56 (2) | C27···H28b | 2.16 (3) |
O14···O15 | 2.235 (6) | C28···C210 | 2.505 (8) |
O14···O24' | 2.898 (6) | C28···H27 | 2.06 (3) |
O14···H18b | 2.58 (3) | C28···H210 | 2.59 (3) |
O14···H110 | 2.56 (3) | C29···C211 | 2.373 (8) |
O14···H24' | 2.33 (5) | C29···C212 | 2.750 (7) |
O15···C17 | 2.346 (6) | C29···C213 | 2.429 (7) |
O15···H16a | 2.03 (3) | C29···H28a | 2.03 (3) |
O15···H16b | 2.05 (3) | C29···H28b | 2.07 (3) |
O15···H17 | 2.60 (2) | C29···H210 | 1.97 (3) |
O15···H114b | 2.61 (4) | C210···O211 | 2.472 (7) |
O15···H231'a | 2.71 (3) | C210···C212 | 2.383 (7) |
C16···C18 | 2.617 (7) | C210···C213 | 2.800 (7) |
C16···H17 | 2.01 (3) | C210···H28b | 2.58 (3) |
C17···C19 | 2.504 (6) | C211···O212 | 2.269 (7) |
C17···H16a | 2.19 (3) | C211···C213 | 2.398 (7) |
C17···H16b | 2.18 (3) | C211···C214 | 2.233 (8) |
C17···H18a | 2.16 (3) | C211···H210 | 1.94 (3) |
C17···H18b | 2.01 (3) | C211···H214a | 2.68 (3) |
C18···C110 | 2.507 (7) | O211···C212 | 2.272 (7) |
C18···H17 | 2.07 (3) | O211···O212 | 2.326 (6) |
C18···H110 | 2.64 (3) | O211···H16b | 2.69 (3) |
C19···C111 | 2.368 (7) | O211···H210 | 2.70 (3) |
C19···C112 | 2.759 (7) | O211···H214a | 2.07 (3) |
C19···C113 | 2.440 (7) | O211···H214b | 2.00 (4) |
C19···H18a | 2.08 (3) | C212···C214 | 2.233 (8) |
C19···H18b | 2.02 (3) | C212···H213 | 2.06 (4) |
C19···H110 | 2.04 (3) | C212···H214a | 2.62 (3) |
C110···O111 | 2.462 (7) | O212···C213 | 2.476 (7) |
C110···C112 | 2.394 (7) | O212···H26a | 2.64 (4) |
C110···C113 | 2.810 (8) | O212···H213 | 2.76 (4) |
C110···H18b | 2.62 (3) | O212···H214a | 1.95 (3) |
C110···H28a | 2.54 (3) | O212···H214b | 2.03 (4) |
C111···O112 | 2.254 (7) | C213···H22 | 2.57 (3) |
C111···C113 | 2.380 (7) | H12···H16' | 2.27 (5) |
C111···C114 | 2.247 (8) | H12···H13 | 2.13 (4) |
C111···H110 | 2.01 (3) | H12'···H131'c | 2.27 (4) |
O111···C112 | 2.269 (7) | H12'···H17 | 2.34 (4) |
O111···O112 | 2.326 (6) | H131'a···H131'b | 1.39 (7) |
O111···O23 | 3.046 (7) | H131'a···H131'c | 2.02 (7) |
O111···H110 | 2.71 (3) | H131'b···H131'c | 1.57 (6) |
O111···H114a | 1.92 (5) | H131'c···H151'b | 2.35 (6) |
O111···H114b | 2.09 (5) | H151'a···H151'b | 1.68 (7) |
O111···H23 | 2.31 (6) | H151'a···H151'c | 1.78 (6) |
C112···C114 | 2.244 (8) | H151'b···H151'c | 1.89 (6) |
C112···H113 | 2.21 (4) | H151'b···H16' | 2.39 (6) |
O112···C113 | 2.463 (6) | H16a···H16b | 1.71 (3) |
O112···H16a | 2.58 (3) | H16a···H17 | 2.35 (4) |
O112···H114a | 1.90 (5) | H17···H18b | 2.29 (5) |
O112···H114b | 2.14 (4) | H18a···H18b | 1.69 (4) |
C21···C21' | 2.529 (7) | H114a···H114b | 1.62 (6) |
C21···C22' | 2.996 (7) | H22···H26' | 2.26 (4) |
C21···C23 | 2.487 (7) | H22···H23 | 2.34 (5) |
C21···O23 | 3.028 (6) | H22'···H231'b | 2.11 (5) |
C21···C27 | 2.856 (7) | H22'···H27 | 2.35 (3) |
C21···C28 | 2.569 (7) | H231'a···H231'b | 1.84 (6) |
C21···C210 | 2.422 (7) | H231'a···H231'c | 1.64 (5) |
C21···C211 | 2.749 (7) | H231'b···H231'c | 1.56 (7) |
C21···C212 | 2.371 (7) | H251'a···H251'b | 1.85 (8) |
C21···H22 | 2.02 (3) | H251'a···H251'c | 1.56 (6) |
C21···H23 | 2.60 (4) | H251'a···H26' | 2.39 (5) |
C21···H213 | 2.09 (3) | H251'b···H251'c | 1.59 (6) |
C22···C22' | 2.550 (6) | H251'c···H26' | 2.19 (5) |
C22···C26' | 2.524 (7) | H26a···H26b | 1.64 (5) |
C22···O23 | 2.432 (5) | H26a···H27 | 2.35 (4) |
C22···C24 | 2.631 (7) | H28a···H28b | 1.61 (4) |
C22···C27 | 2.539 (7) | H28b···H210 | 2.38 (5) |
C22···C29 | 2.584 (7) | H214a···H214b | 1.84 (6) |
C12—C11—C19 | 123.6 (3) | C22—C21—C29 | 123.1 (4) |
C12—C11—C113 | 116.9 (3) | C22—C21—C213 | 116.4 (4) |
C19—C11—C113 | 119.3 (3) | C29—C21—C213 | 120.4 (4) |
C11—C12—C11' | 110.8 (3) | C21—C22—C21' | 111.2 (3) |
C11—C12—C13 | 108.5 (4) | C21—C22—C23 | 108.1 (4) |
C11—C12—H12 | 112.0 (17) | C21—C22—H22 | 107 (2) |
C11'—C12—C13 | 114.6 (4) | C21'—C22—C23 | 115.1 (4) |
C11'—C12—H12 | 105.4 (17) | C21'—C22—H22 | 102 (2) |
C13—C12—H12 | 105.5 (16) | C23—C22—H22 | 113.3 (17) |
C12—C11'—C12' | 122.3 (4) | C22—C21'—C22' | 122.5 (4) |
C12—C11'—C16' | 119.7 (4) | C22—C21'—C26' | 119.4 (4) |
C12'—C11'—C16' | 117.8 (4) | C22'—C21'—C26' | 118.0 (4) |
C11'—C12'—C13' | 121.9 (5) | C21'—C22'—C23' | 122.2 (5) |
C11'—C12'—H12' | 119.8 (16) | C21'—C22'—H22' | 115.6 (17) |
C13'—C12'—H12' | 118.3 (16) | C23'—C22'—H22' | 122.1 (17) |
C12'—C13'—O13' | 124.8 (5) | C22'—C23'—O23' | 125.3 (4) |
C12'—C13'—C14' | 119.2 (4) | C22'—C23'—C24' | 119.2 (4) |
O13'—C13'—C14' | 115.9 (4) | O23'—C23'—C24' | 115.5 (4) |
C13'—O13'—C131' | 117.0 (4) | C23'—O23'—C231' | 117.8 (4) |
O13'—C131'—H131'a | 105 (3) | O23'—C231'—H231'a | 101 (2) |
O13'—C131'—H131'b | 107 (3) | O23'—C231'—H231'b | 104 (2) |
O13'—C131'—H131'c | 115 (2) | O23'—C231'—H231'c | 118 (2) |
H131'a—C131'—H131'b | 84 (3) | H231'a—C231'—H231'b | 127 (3) |
H131'a—C131'—H131'c | 137 (4) | H231'a—C231'—H231'c | 113 (3) |
H131'b—C131'—H131'c | 99 (3) | H231'b—C231'—H231'c | 95 (3) |
C13'—C14'—O14' | 118.2 (4) | C23'—C24'—O24' | 118.0 (4) |
C13'—C14'—C15' | 119.1 (4) | C23'—C24'—C25' | 119.2 (4) |
O14'—C14'—C15' | 122.7 (5) | O24'—C24'—C25' | 122.7 (5) |
C14'—O14'—H14' | 103 (4) | C24'—O24'—H24' | 104 (4) |
C14'—C15'—O15' | 113.6 (4) | C24'—C25'—O25' | 114.2 (4) |
C14'—C15'—C16' | 121.7 (5) | C24'—C25'—C26' | 120.9 (5) |
O15'—C15'—C16' | 124.7 (4) | O25'—C25'—C26' | 124.9 (4) |
C15'—O15'—C151' | 117.1 (4) | C25'—O25'—C251' | 118.8 (4) |
O15'—C151'—H151'a | 106.4 (18) | O25'—C251'—H251'a | 104 (3) |
O15'—C151'—H151'b | 107 (2) | O25'—C251'—H251'b | 116 (3) |
O15'—C151'—H151'c | 98.0 (18) | O25'—C251'—H251'c | 107 (2) |
H151'a—C151'—H151'b | 113 (4) | H251'a—C251'—H251'b | 124 (4) |
H151'a—C151'—H151'c | 109 (3) | H251'a—C251'—H251'c | 105 (3) |
H151'b—C151'—H151'c | 121 (3) | H251'b—C251'—H251'c | 99 (3) |
C11'—C16'—C15' | 120.3 (4) | C21'—C26'—C25' | 120.5 (4) |
C11'—C16'—H16' | 117 (3) | C21'—C26'—H26' | 119.1 (18) |
C15'—C16'—H16' | 123 (3) | C25'—C26'—H26' | 120.3 (18) |
C12—C13—O13 | 110.3 (3) | C22—C23—O23 | 108.8 (4) |
C12—C13—C14 | 119.2 (4) | C22—C23—C24 | 119.2 (4) |
C12—C13—C17 | 112.9 (4) | C22—C23—C27 | 113.3 (4) |
O13—C13—C14 | 105.4 (3) | O23—C23—C24 | 102.8 (3) |
O13—C13—C17 | 107.5 (4) | O23—C23—C27 | 110.6 (4) |
C14—C13—C17 | 100.5 (3) | C24—C23—C27 | 101.6 (4) |
C13—O13—H13 | 108 (2) | C23—O23—H23 | 106 (3) |
C13—C14—O14 | 129.9 (5) | C23—C24—O24 | 130.6 (5) |
C13—C14—O15 | 108.9 (4) | C23—C24—O25 | 107.9 (4) |
O14—C14—O15 | 121.1 (5) | O24—C24—O25 | 121.5 (5) |
C14—O15—C16 | 109.1 (4) | C24—O25—C26 | 110.4 (4) |
O15—C16—C17 | 102.9 (4) | O25—C26—C27 | 102.5 (4) |
O15—C16—H16a | 105.5 (17) | O25—C26—H26a | 106 (2) |
O15—C16—H16b | 105.4 (15) | O25—C26—H26b | 105.2 (16) |
C17—C16—H16a | 118.0 (16) | C27—C26—H26a | 118.9 (18) |
C17—C16—H16b | 114.6 (13) | C27—C26—H26b | 115.3 (18) |
H16a—C16—H16b | 109 (2) | H26a—C26—H26b | 108 (2) |
C13—C17—C16 | 102.3 (4) | C23—C27—C26 | 102.3 (4) |
C13—C17—C18 | 111.3 (4) | C23—C27—C28 | 112.8 (4) |
C13—C17—H17 | 106.7 (15) | C23—C27—H27 | 104.9 (16) |
C16—C17—C18 | 119.7 (5) | C26—C27—C28 | 119.2 (4) |
C16—C17—H17 | 106.0 (14) | C26—C27—H27 | 105.7 (16) |
C18—C17—H17 | 110.0 (15) | C28—C27—H27 | 110.7 (17) |
C17—C18—C19 | 111.4 (4) | C27—C28—C29 | 111.0 (4) |
C17—C18—H18a | 110.0 (16) | C27—C28—H28a | 112 (2) |
C17—C18—H18b | 109 (2) | C27—C28—H28b | 116 (2) |
C19—C18—H18a | 103.9 (15) | C29—C28—H28a | 105.2 (19) |
C19—C18—H18b | 110 (2) | C29—C28—H28b | 106.8 (16) |
H18a—C18—H18b | 112 (3) | H28a—C28—H28b | 105 (2) |
C11—C19—C18 | 121.5 (4) | C21—C29—C28 | 123.0 (5) |
C11—C19—C110 | 120.3 (4) | C21—C29—C210 | 119.6 (5) |
C18—C19—C110 | 118.1 (4) | C28—C29—C210 | 117.4 (4) |
C19—C110—C111 | 118.0 (5) | C29—C210—C211 | 119.0 (5) |
C19—C110—H110 | 120 (2) | C29—C210—H210 | 119 (2) |
C111—C110—H110 | 122 (2) | C211—C210—H210 | 122 (2) |
C110—C111—O111 | 127.2 (5) | C210—C211—O211 | 128.9 (5) |
C110—C111—C112 | 122.8 (5) | C210—C211—C212 | 121.3 (5) |
O111—C111—C112 | 110.0 (4) | O211—C211—C212 | 109.7 (5) |
C111—O111—C114 | 104.8 (4) | C211—O211—C214 | 104.2 (4) |
C111—C112—O112 | 110.2 (5) | C211—C212—O212 | 109.8 (5) |
C111—C112—C113 | 121.1 (5) | C211—C212—C213 | 121.6 (5) |
O112—C112—C113 | 128.6 (5) | O212—C212—C213 | 128.6 (5) |
C112—O112—C114 | 105.6 (4) | C212—O212—C214 | 103.9 (4) |
C11—C113—C112 | 118.3 (4) | C21—C213—C212 | 118.1 (4) |
C11—C113—H113 | 119.0 (18) | C21—C213—H213 | 120 (2) |
C112—C113—H113 | 122.6 (18) | C212—C213—H213 | 121 (2) |
O111—C114—O112 | 107.7 (4) | O211—C214—O212 | 107.4 (4) |
O111—C114—H114a | 112 (4) | O211—C214—H214a | 108.8 (18) |
O111—C114—H114b | 108 (2) | O211—C214—H214b | 108 (2) |
O112—C114—H114a | 110 (3) | O212—C214—H214a | 99 (2) |
O112—C114—H114b | 111 (3) | O212—C214—H214b | 110 (2) |
H114a—C114—H114b | 109 (4) | H214a—C214—H214b | 122 (3) |
Experimental details
Crystal data | |
Chemical formula | C21H20O8 |
Mr | 400.38 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 300 |
a, b, c (Å) | 7.854 (1), 9.384 (1), 13.230 (2) |
α, β, γ (°) | 101.563 (2), 103.699 (2), 90.184 (2) |
V (Å3) | 926.8 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.20 × 0.10 × 0.05 |
Data collection | |
Diffractometer | Bruker SMART CCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed (F2 > 2σF2) reflections | 10605, 4460, 2592 |
Rint | 0.068 |
(sin θ/λ)max (Å−1) | 0.669 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.044, 1.07 |
No. of reflections | 4460 |
No. of parameters | 681 |
No. of restraints | 3941.12 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.20, −0.18 |
Computer programs: SMART (Siemens, 1995), SAINT (Siemens, 1995), SAINT, Xtal3.5 GENTAN (Hall et al., 1995), Xtal3.5 CRYLSQ, Xtal3.5 PIG and ORTEP, Xtal3.5 BONDLA and CIFIO.
Some years ago (Shaari & Waterman, 1994), the title compound, (I), was isolated from Casearia clarkei King, a small lowland rainforest tree endemic to Malaysia and Singapore, and an assignment of the structure was made on the basis of spectroscopic and chiroptical evidence. An X-ray structure determination was considered desirable at the time, the better to secure the assignment, but specimens were only available as fine flakes of insufficient substance to be amenable to such a study by our contemporary single-counter diffractometer instrumentation. The advent of area-detector instrumentation has now permitted an effective attack on this problem, yielding a definitive assignment of the structure which confirms that proposed previously.
The results of the room-temperature single-crystal X-ray study of (I) are consistent with the stoichiometry, connectivity and stereochemistry proposed previously, i.e. two molecules (n = 1,2), pseudo-symmetrically related, comprise the asymmetric unit of the structure and the unit cell in the uncommon triclinic space group P1. The skeletal form appears to be previously unrecorded in the Cambridge Structural Database (Allen & Kennard, 1993), but offers no surprises in respect of bond lengths and angles generally and these have been deposited. The absolute configuration was not assignable from the crystallographic work and follows that previously defined in the chemistry. The two molecules of the asymmetric unit are of the same chirality and of similar conformation; only one is shown in Fig. 1. The plane of the pendant ring is quasi-normal to that of the fused system; the unit-cell contents as displayed in Fig. 2 show the pseudo-symmetry, and the hydrogen bonding and parallel packing of the major molecular planes. The numbering of the non-H atoms (not systematic) within each molecule (n = 1,2 to be prefixed) is as shown in the Scheme above.