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A room-temperature single-crystal X-ray structure determination of the title compound, C21H20O8, confirms the stereochemical assignment made previously on the basis of spectroscopic studies [Shaari & Waterman (1994). J. Nat. Prod. 57, 720–724].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S010827019901358X/ja1004sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010827019901358X/ja1004Isup2.hkl
Contains datablock I

CCDC reference: 142750

Comment top

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.

Experimental top

Please provide some synthetic/isolation details.

Refinement top

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.

Computing details top

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.

Figures top
[Figure 1] Fig. 1. Projection of molecule n = 1 (molecule 2 is similar) normal to the fused-ring plane. Displacement ellipsoids are shown at 20% probability levels for the non-H atoms and H atoms are shown with arbitrary radii of 0.1 Å.
[Figure 2] Fig. 2. Unit-cell contents projected down a, showing intermolecular hydrogen bonds within the cell.
(I) top
Crystal data top
C21H20O8V = 926.8 (2) Å3
Mr = 400.38Z = 2
Triclinic, P1Dx = 1.435 Mg m3
Hall symbol: p 1Mo Kα radiation, λ = 0.71073 Å
a = 7.854 (1) ÅCell parameters from 1868 reflections
b = 9.384 (1) Åθ = 2–29°
c = 13.230 (2) ŵ = 0.11 mm1
α = 101.563 (2)°T = 300 K
β = 103.699 (2)°Plate, colourless
γ = 90.184 (2)°0.20 × 0.10 × 0.05 mm
Data collection top
Bruker SMART CCD
diffractometer
Rint = 0.068
ω scansθmax = 28.4°, θmin = 1.6°
10605 measured reflectionsh = 1010
4460 independent reflectionsk = 1212
2592 reflections with F2 > 2σF2l = 1818
Refinement top
Refinement on F24163.51 constraints
Least-squares matrix: fullAll H-atom parameters refined
R[F2 > 2σ(F2)] = 0.040Weighting scheme based on measured s.u.'s
wR(F2) = 0.044(Δ/σ)max = 0.02
S = 1.07Δρmax = 0.20 e Å3
4460 reflectionsΔρmin = 0.18 e Å3
681 parametersExtinction correction: Zachariasen
3941.12 restraintsExtinction coefficient: 2063.4 (7)
Crystal data top
C21H20O8γ = 90.184 (2)°
Mr = 400.38V = 926.8 (2) Å3
Triclinic, P1Z = 2
a = 7.854 (1) ÅMo Kα radiation
b = 9.384 (1) ŵ = 0.11 mm1
c = 13.230 (2) ÅT = 300 K
α = 101.563 (2)°0.20 × 0.10 × 0.05 mm
β = 103.699 (2)°
Data collection top
Bruker SMART CCD
diffractometer
2592 reflections with F2 > 2σF2
10605 measured reflectionsRint = 0.068
4460 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0403941.12 restraints
wR(F2) = 0.044All H-atom parameters refined
S = 1.07Δρmax = 0.20 e Å3
4460 reflectionsΔρmin = 0.18 e Å3
681 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C110.000000.500000.000000.0332 (17)
C120.1608 (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)
C130.1875 (6)0.7130 (5)0.0030 (3)0.0317 (16)
O130.2507 (5)0.6885 (4)0.1165 (3)0.0410 (13)
C140.3114 (6)0.8197 (5)0.0419 (3)0.038 (2)
O140.4438 (5)0.7960 (4)0.0690 (3)0.0566 (15)
O150.2573 (5)0.9572 (4)0.0424 (3)0.0464 (14)
C160.0896 (7)0.9531 (5)0.0081 (4)0.040 (2)
C170.0218 (6)0.8080 (5)0.0270 (4)0.0324 (17)
C180.1140 (7)0.7386 (5)0.0292 (4)0.0371 (19)
C190.1333 (5)0.5807 (5)0.0205 (3)0.0337 (17)
C1100.2862 (6)0.5138 (5)0.0396 (4)0.038 (2)
C1110.2960 (6)0.3694 (5)0.0414 (3)0.040 (2)
O1110.4311 (5)0.2814 (5)0.0634 (3)0.0555 (15)
C1120.1636 (7)0.2866 (5)0.0260 (4)0.040 (2)
O1120.2049 (5)0.1430 (4)0.0375 (3)0.0629 (17)
C1130.0177 (6)0.3480 (5)0.0023 (3)0.043 (2)
C1140.3846 (8)0.1413 (6)0.0462 (5)0.062 (3)
C210.2539 (5)0.1847 (5)0.6569 (3)0.0335 (18)
C220.4146 (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)
C230.4421 (6)0.3984 (5)0.6569 (4)0.0341 (17)
O230.5183 (5)0.4348 (4)0.7714 (3)0.0390 (13)
C240.5678 (6)0.4783 (5)0.6132 (3)0.038 (2)
O240.6971 (5)0.4382 (4)0.5831 (3)0.0552 (15)
O250.5141 (5)0.6164 (4)0.6139 (3)0.0490 (14)
C260.3455 (7)0.6335 (5)0.6472 (4)0.044 (2)
C270.2761 (6)0.4774 (5)0.6285 (4)0.0328 (18)
C280.1397 (6)0.4424 (5)0.6838 (4)0.036 (2)
C290.1261 (6)0.2796 (5)0.6814 (4)0.0336 (17)
C2100.0229 (6)0.2251 (6)0.7060 (4)0.043 (2)
C2110.0387 (6)0.0819 (6)0.7055 (4)0.044 (2)
O2110.1730 (5)0.0048 (5)0.7270 (3)0.0616 (16)
C2120.0908 (7)0.0112 (6)0.6841 (4)0.044 (2)
O2120.0460 (6)0.1506 (5)0.6928 (3)0.0652 (16)
C2130.2352 (6)0.0362 (5)0.6578 (3)0.043 (2)
C2140.1379 (7)0.1454 (6)0.6938 (5)0.063 (3)
H120.273 (4)0.505 (3)0.005 (2)0.030 (8)*
H12'0.106 (4)0.645 (3)0.207 (2)0.023 (8)*
H131'a0.277 (7)0.863 (6)0.433 (5)0.18 (3)*
H131'b0.406 (5)0.763 (4)0.454 (3)0.068 (12)*
H131'c0.364 (5)0.708 (4)0.330 (3)0.098 (15)*
H14'0.201 (8)0.525 (6)0.473 (5)0.20 (3)*
H151'a0.630 (5)0.377 (4)0.305 (3)0.068 (11)*
H151'b0.613 (6)0.483 (5)0.219 (4)0.101 (17)*
H151'c0.486 (5)0.313 (4)0.221 (3)0.091 (14)*
H16'0.366 (4)0.496 (3)0.144 (3)0.037 (11)*
H130.319 (4)0.608 (3)0.138 (2)0.037 (10)*
H16a0.017 (4)1.046 (3)0.052 (2)0.029 (8)*
H16b0.125 (3)0.961 (3)0.074 (2)0.027 (8)*
H170.023 (3)0.820 (2)0.104 (2)0.013 (7)*
H18a0.069 (4)0.733 (3)0.116 (2)0.048 (9)*
H18b0.219 (4)0.790 (3)0.000 (2)0.048 (11)*
H1100.377 (4)0.569 (3)0.049 (2)0.038 (10)*
H1130.093 (5)0.282 (4)0.015 (3)0.084 (13)*
H114a0.395 (6)0.073 (5)0.096 (4)0.10 (2)*
H114b0.478 (6)0.125 (4)0.031 (4)0.111 (16)*
H220.509 (4)0.183 (3)0.652 (2)0.046 (10)*
H22'0.159 (3)0.209 (3)0.451 (2)0.012 (8)*
H231'a0.128 (5)0.201 (4)0.191 (3)0.077 (14)*
H231'b0.078 (5)0.205 (4)0.335 (4)0.107 (16)*
H231'c0.004 (5)0.323 (4)0.286 (3)0.082 (14)*
H24'0.431 (5)0.032 (5)0.179 (4)0.08 (2)*
H251'a0.760 (6)0.111 (5)0.434 (4)0.12 (2)*
H251'b0.921 (7)0.081 (5)0.358 (4)0.14 (2)*
H251'c0.856 (5)0.038 (4)0.442 (3)0.051 (12)*
H26'0.643 (3)0.102 (3)0.520 (2)0.024 (8)*
H230.486 (6)0.368 (5)0.795 (4)0.12 (2)*
H26a0.277 (4)0.701 (4)0.605 (3)0.066 (12)*
H26b0.380 (3)0.688 (3)0.726 (2)0.032 (8)*
H270.234 (3)0.446 (3)0.552 (2)0.029 (8)*
H28a0.169 (4)0.490 (3)0.761 (2)0.049 (10)*
H28b0.014 (4)0.473 (3)0.654 (2)0.040 (9)*
H2100.103 (4)0.283 (3)0.718 (2)0.021 (9)*
H2130.328 (4)0.031 (4)0.643 (3)0.051 (11)*
H214a0.196 (4)0.180 (4)0.608 (3)0.068 (12)*
H214b0.162 (5)0.201 (4)0.747 (3)0.084 (14)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C110.032 (2)0.038 (2)0.029 (2)0.0022 (18)0.0098 (16)0.0084 (16)
C120.029 (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)
C130.032 (2)0.034 (2)0.030 (2)0.0000 (16)0.0067 (15)0.0048 (15)
O130.0506 (16)0.0375 (16)0.0349 (15)0.0089 (13)0.0001 (12)0.0078 (12)
C140.037 (2)0.042 (3)0.035 (2)0.008 (2)0.0001 (17)0.0042 (17)
O140.0386 (16)0.0534 (18)0.078 (2)0.0075 (13)0.0245 (15)0.0112 (14)
O150.0444 (17)0.0318 (16)0.0631 (18)0.0032 (13)0.0127 (13)0.0059 (12)
C160.046 (3)0.035 (2)0.040 (2)0.0035 (19)0.008 (2)0.0083 (17)
C170.034 (2)0.029 (2)0.035 (2)0.0028 (16)0.0065 (17)0.0066 (15)
C180.035 (2)0.030 (2)0.046 (2)0.0059 (18)0.0122 (18)0.0074 (16)
C190.037 (2)0.037 (2)0.0268 (19)0.0030 (17)0.0067 (16)0.0043 (15)
C1100.033 (2)0.044 (3)0.035 (2)0.004 (2)0.0108 (17)0.0055 (17)
C1110.038 (2)0.049 (3)0.032 (2)0.011 (2)0.0087 (17)0.0072 (17)
O1110.0458 (16)0.0507 (18)0.0700 (19)0.0144 (14)0.0228 (14)0.0103 (14)
C1120.043 (2)0.037 (2)0.040 (2)0.009 (2)0.0123 (18)0.0125 (17)
O1120.061 (2)0.0408 (18)0.087 (2)0.0134 (14)0.0314 (17)0.0200 (14)
C1130.050 (3)0.039 (2)0.039 (2)0.001 (2)0.0089 (18)0.0157 (17)
C1140.063 (3)0.049 (3)0.075 (3)0.021 (3)0.025 (3)0.017 (3)
C210.032 (2)0.041 (2)0.027 (2)0.0072 (18)0.0073 (16)0.0034 (16)
C220.029 (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)
C230.034 (2)0.038 (2)0.031 (2)0.0048 (17)0.0077 (16)0.0073 (15)
O230.0436 (15)0.0419 (16)0.0314 (14)0.0079 (12)0.0034 (11)0.0051 (11)
C240.040 (2)0.043 (3)0.030 (2)0.011 (2)0.0031 (17)0.0100 (17)
O240.0368 (16)0.064 (2)0.0648 (19)0.0029 (14)0.0218 (14)0.0206 (14)
O250.0479 (16)0.0387 (17)0.0603 (18)0.0063 (13)0.0155 (13)0.0157 (13)
C260.049 (3)0.038 (2)0.044 (3)0.000 (2)0.008 (2)0.008 (2)
C270.036 (2)0.030 (2)0.032 (2)0.0062 (16)0.0027 (17)0.0074 (16)
C280.035 (2)0.037 (2)0.037 (2)0.0026 (18)0.0065 (18)0.0080 (17)
C290.033 (2)0.038 (2)0.030 (2)0.0019 (18)0.0018 (16)0.0096 (15)
C2100.031 (2)0.050 (3)0.048 (2)0.007 (2)0.0127 (19)0.015 (2)
C2110.041 (2)0.055 (3)0.036 (2)0.011 (2)0.0089 (18)0.0150 (19)
O2110.0467 (17)0.068 (2)0.070 (2)0.0152 (15)0.0201 (14)0.0235 (15)
C2120.055 (3)0.039 (2)0.037 (2)0.013 (2)0.009 (2)0.0074 (17)
O2120.073 (2)0.0416 (17)0.081 (2)0.0120 (14)0.0276 (17)0.0180 (14)
C2130.047 (2)0.035 (2)0.047 (2)0.000 (2)0.019 (2)0.0076 (17)
C2140.067 (3)0.055 (3)0.067 (3)0.025 (2)0.011 (3)0.019 (2)
Geometric parameters (Å, º) top
C11—C121.529 (5)C21—C221.542 (7)
C11—C191.399 (5)C21—C291.396 (7)
C11—C1131.429 (5)C21—C2131.403 (7)
C12—C11'1.534 (6)C22—C21'1.523 (6)
C12—C131.537 (7)C22—C231.531 (6)
C12—H121.02 (3)C22—H220.93 (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'a1.09 (6)C231'—H231'a0.95 (4)
C131'—H131'b0.98 (3)C231'—H231'b1.10 (5)
C131'—H131'c1.08 (5)C231'—H231'c1.01 (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'a1.02 (4)C251'—H251'a0.98 (6)
C151'—H151'b1.00 (5)C251'—H251'b1.11 (6)
C151'—H151'c1.16 (4)C251'—H251'c0.98 (3)
C16'—H16'0.76 (3)C26'—H26'0.93 (3)
C13—O131.436 (6)C23—O231.460 (6)
C13—C141.531 (7)C23—C241.520 (8)
C13—C171.501 (6)C23—C271.509 (6)
O13—H130.88 (3)O23—H230.82 (5)
C14—O141.211 (7)C24—O241.211 (7)
C14—O151.355 (6)C24—O251.363 (6)
O15—C161.490 (7)O25—C261.491 (7)
C16—C171.509 (7)C26—C271.513 (7)
C16—H16a1.03 (3)C26—H26a1.00 (4)
C16—H16b1.07 (3)C26—H26b1.03 (3)
C17—C181.517 (7)C27—C281.501 (8)
C17—H170.98 (3)C27—H270.97 (3)
C18—C191.514 (7)C28—C291.525 (7)
C18—H18a1.11 (3)C28—H28a1.00 (3)
C18—H18b0.92 (3)C28—H28b1.03 (3)
C19—C1101.409 (7)C29—C2101.407 (7)
C110—C1111.353 (7)C210—C2111.347 (8)
C110—H1100.93 (3)C210—H2100.86 (3)
C111—O1111.396 (6)C211—O2111.392 (7)
C111—C1121.374 (7)C211—C2121.386 (7)
O111—C1141.439 (8)O211—C2141.438 (7)
C112—O1121.374 (6)C212—O2121.387 (7)
C112—C1131.358 (7)C212—C2131.361 (8)
O112—C1141.443 (8)O212—C2141.448 (8)
C113—H1131.16 (4)C213—H2130.99 (3)
C114—H114a0.84 (4)C214—H214a1.09 (4)
C114—H114b1.15 (4)C214—H214b1.01 (4)
C11···C11'2.522 (5)C22···C2132.504 (7)
C11···C12'2.976 (5)C22···H22'2.61 (2)
C11···C132.487 (5)C22···H26'2.65 (3)
C11···O133.010 (4)C22···H232.33 (5)
C11···C172.851 (4)C22···H272.65 (3)
C11···C182.542 (5)C22···H2132.65 (4)
C11···C1102.435 (5)C21'···C23'2.416 (6)
C11···C1112.750 (5)C21'···C24'2.802 (6)
C11···C1122.393 (5)C21'···C25'2.419 (7)
C11···H122.13 (3)C21'···C232.577 (6)
C11···H1132.23 (4)C21'···H221.94 (3)
C12···C12'2.557 (6)C21'···H22'1.89 (3)
C12···C16'2.541 (8)C21'···H26'2.02 (3)
C12···O132.440 (6)C22'···O23'2.430 (6)
C12···C142.647 (7)C22'···C231'2.873 (7)
C12···C172.532 (7)C22'···C24'2.403 (7)
C12···C192.581 (7)C22'···C25'2.753 (7)
C12···C1132.520 (7)C22'···C26'2.387 (7)
C12···H12'2.70 (2)C22'···H231'b2.57 (4)
C12···H16'2.59 (4)C23'···C231'2.381 (7)
C12···H132.41 (3)C23'···O24'2.379 (7)
C12···H172.66 (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'b2.56 (4)
C11'···C132.584 (7)C23'···H231'c2.68 (4)
C11'···H122.05 (2)O23'···C24'2.343 (6)
C11'···H12'1.98 (3)O23'···O24'2.637 (6)
C11'···H16'1.87 (3)O23'···H16a2.41 (3)
C12'···O13'2.436 (6)O23'···H22'2.63 (2)
C12'···C131'2.851 (6)O23'···H231'a1.86 (4)
C12'···C14'2.404 (8)O23'···H231'b1.99 (5)
C12'···C15'2.741 (7)O23'···H231'c2.09 (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'···H18b2.73 (3)
O13'···O14'2.650 (6)C25'···C251'2.391 (8)
O13'···H12'2.61 (3)C25'···H24'2.33 (5)
O13'···H131'a2.00 (6)C25'···H251'a2.52 (5)
O13'···H131'b1.94 (4)C25'···H251'c2.58 (3)
O13'···H131'c2.11 (5)C25'···H26'2.02 (3)
O13'···H26a2.43 (3)O25'···C26'2.443 (7)
C131'···H12'2.58 (2)O25'···H24'2.24 (4)
C14'···O15'2.295 (6)O25'···H251'a1.91 (5)
C14'···C16'2.391 (6)O25'···H251'b2.14 (5)
C14'···H14'1.82 (7)O25'···H251'c1.94 (3)
C14'···H231'c2.62 (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'···O242.868 (7)C26'···H222.45 (3)
O14'···H28b2.71 (3)C26'···H251'c2.66 (4)
C15'···C151'2.393 (8)C23···O242.484 (7)
C15'···H14'2.33 (6)C23···O252.332 (7)
C15'···H151'b2.64 (4)C23···C262.353 (7)
C15'···H151'c2.52 (4)C23···C282.507 (7)
C15'···H16'1.89 (3)C23···C292.832 (7)
O15'···C16'2.441 (7)C23···H222.08 (3)
O15'···H131'c2.79 (4)C23···H231.86 (5)
O15'···H14'2.08 (5)C23···H271.99 (3)
O15'···H151'a1.97 (4)O23···C242.329 (7)
O15'···H151'b1.97 (4)O23···O243.141 (6)
O15'···H151'c1.96 (3)O23···O252.939 (6)
O15'···H16'2.62 (4)O23···C262.865 (7)
C151'···C16'2.826 (9)O23···C272.441 (6)
C151'···H16'2.60 (4)O23···C282.931 (6)
C16'···H122.52 (3)O23···H132.05 (3)
C13···O142.487 (6)O23···H222.55 (3)
C13···O152.351 (6)O23···H26b2.73 (3)
C13···C162.344 (7)O23···H28a2.77 (3)
C13···C182.491 (7)C24···C262.344 (7)
C13···C192.850 (6)C24···C272.347 (7)
C13···H122.06 (3)C24···H272.55 (3)
C13···H131.90 (3)O24···O252.247 (6)
C13···H172.02 (2)O24···H14'2.11 (7)
O13···C142.361 (6)O24···H28b2.44 (3)
O13···O143.181 (6)O24···H2102.73 (3)
O13···O152.951 (5)O25···C272.343 (6)
O13···C162.800 (6)O25···H131'b2.73 (4)
O13···C172.369 (5)O25···H26a2.01 (4)
O13···C182.823 (6)O25···H26b2.02 (3)
O13···O232.905 (5)O25···H272.58 (2)
O13···H122.52 (3)C26···C282.600 (8)
O13···H16b2.64 (2)C26···H272.01 (2)
O13···H18a2.54 (3)C27···C292.495 (7)
O13···H214b2.48 (4)C27···H26a2.18 (4)
C14···C162.320 (8)C27···H26b2.16 (3)
C14···C172.330 (7)C27···H28a2.10 (4)
C14···H172.56 (2)C27···H28b2.16 (3)
O14···O152.235 (6)C28···C2102.505 (8)
O14···O24'2.898 (6)C28···H272.06 (3)
O14···H18b2.58 (3)C28···H2102.59 (3)
O14···H1102.56 (3)C29···C2112.373 (8)
O14···H24'2.33 (5)C29···C2122.750 (7)
O15···C172.346 (6)C29···C2132.429 (7)
O15···H16a2.03 (3)C29···H28a2.03 (3)
O15···H16b2.05 (3)C29···H28b2.07 (3)
O15···H172.60 (2)C29···H2101.97 (3)
O15···H114b2.61 (4)C210···O2112.472 (7)
O15···H231'a2.71 (3)C210···C2122.383 (7)
C16···C182.617 (7)C210···C2132.800 (7)
C16···H172.01 (3)C210···H28b2.58 (3)
C17···C192.504 (6)C211···O2122.269 (7)
C17···H16a2.19 (3)C211···C2132.398 (7)
C17···H16b2.18 (3)C211···C2142.233 (8)
C17···H18a2.16 (3)C211···H2101.94 (3)
C17···H18b2.01 (3)C211···H214a2.68 (3)
C18···C1102.507 (7)O211···C2122.272 (7)
C18···H172.07 (3)O211···O2122.326 (6)
C18···H1102.64 (3)O211···H16b2.69 (3)
C19···C1112.368 (7)O211···H2102.70 (3)
C19···C1122.759 (7)O211···H214a2.07 (3)
C19···C1132.440 (7)O211···H214b2.00 (4)
C19···H18a2.08 (3)C212···C2142.233 (8)
C19···H18b2.02 (3)C212···H2132.06 (4)
C19···H1102.04 (3)C212···H214a2.62 (3)
C110···O1112.462 (7)O212···C2132.476 (7)
C110···C1122.394 (7)O212···H26a2.64 (4)
C110···C1132.810 (8)O212···H2132.76 (4)
C110···H18b2.62 (3)O212···H214a1.95 (3)
C110···H28a2.54 (3)O212···H214b2.03 (4)
C111···O1122.254 (7)C213···H222.57 (3)
C111···C1132.380 (7)H12···H16'2.27 (5)
C111···C1142.247 (8)H12···H132.13 (4)
C111···H1102.01 (3)H12'···H131'c2.27 (4)
O111···C1122.269 (7)H12'···H172.34 (4)
O111···O1122.326 (6)H131'a···H131'b1.39 (7)
O111···O233.046 (7)H131'a···H131'c2.02 (7)
O111···H1102.71 (3)H131'b···H131'c1.57 (6)
O111···H114a1.92 (5)H131'c···H151'b2.35 (6)
O111···H114b2.09 (5)H151'a···H151'b1.68 (7)
O111···H232.31 (6)H151'a···H151'c1.78 (6)
C112···C1142.244 (8)H151'b···H151'c1.89 (6)
C112···H1132.21 (4)H151'b···H16'2.39 (6)
O112···C1132.463 (6)H16a···H16b1.71 (3)
O112···H16a2.58 (3)H16a···H172.35 (4)
O112···H114a1.90 (5)H17···H18b2.29 (5)
O112···H114b2.14 (4)H18a···H18b1.69 (4)
C21···C21'2.529 (7)H114a···H114b1.62 (6)
C21···C22'2.996 (7)H22···H26'2.26 (4)
C21···C232.487 (7)H22···H232.34 (5)
C21···O233.028 (6)H22'···H231'b2.11 (5)
C21···C272.856 (7)H22'···H272.35 (3)
C21···C282.569 (7)H231'a···H231'b1.84 (6)
C21···C2102.422 (7)H231'a···H231'c1.64 (5)
C21···C2112.749 (7)H231'b···H231'c1.56 (7)
C21···C2122.371 (7)H251'a···H251'b1.85 (8)
C21···H222.02 (3)H251'a···H251'c1.56 (6)
C21···H232.60 (4)H251'a···H26'2.39 (5)
C21···H2132.09 (3)H251'b···H251'c1.59 (6)
C22···C22'2.550 (6)H251'c···H26'2.19 (5)
C22···C26'2.524 (7)H26a···H26b1.64 (5)
C22···O232.432 (5)H26a···H272.35 (4)
C22···C242.631 (7)H28a···H28b1.61 (4)
C22···C272.539 (7)H28b···H2102.38 (5)
C22···C292.584 (7)H214a···H214b1.84 (6)
C12—C11—C19123.6 (3)C22—C21—C29123.1 (4)
C12—C11—C113116.9 (3)C22—C21—C213116.4 (4)
C19—C11—C113119.3 (3)C29—C21—C213120.4 (4)
C11—C12—C11'110.8 (3)C21—C22—C21'111.2 (3)
C11—C12—C13108.5 (4)C21—C22—C23108.1 (4)
C11—C12—H12112.0 (17)C21—C22—H22107 (2)
C11'—C12—C13114.6 (4)C21'—C22—C23115.1 (4)
C11'—C12—H12105.4 (17)C21'—C22—H22102 (2)
C13—C12—H12105.5 (16)C23—C22—H22113.3 (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'a105 (3)O23'—C231'—H231'a101 (2)
O13'—C131'—H131'b107 (3)O23'—C231'—H231'b104 (2)
O13'—C131'—H131'c115 (2)O23'—C231'—H231'c118 (2)
H131'a—C131'—H131'b84 (3)H231'a—C231'—H231'b127 (3)
H131'a—C131'—H131'c137 (4)H231'a—C231'—H231'c113 (3)
H131'b—C131'—H131'c99 (3)H231'b—C231'—H231'c95 (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'a106.4 (18)O25'—C251'—H251'a104 (3)
O15'—C151'—H151'b107 (2)O25'—C251'—H251'b116 (3)
O15'—C151'—H151'c98.0 (18)O25'—C251'—H251'c107 (2)
H151'a—C151'—H151'b113 (4)H251'a—C251'—H251'b124 (4)
H151'a—C151'—H151'c109 (3)H251'a—C251'—H251'c105 (3)
H151'b—C151'—H151'c121 (3)H251'b—C251'—H251'c99 (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—O13110.3 (3)C22—C23—O23108.8 (4)
C12—C13—C14119.2 (4)C22—C23—C24119.2 (4)
C12—C13—C17112.9 (4)C22—C23—C27113.3 (4)
O13—C13—C14105.4 (3)O23—C23—C24102.8 (3)
O13—C13—C17107.5 (4)O23—C23—C27110.6 (4)
C14—C13—C17100.5 (3)C24—C23—C27101.6 (4)
C13—O13—H13108 (2)C23—O23—H23106 (3)
C13—C14—O14129.9 (5)C23—C24—O24130.6 (5)
C13—C14—O15108.9 (4)C23—C24—O25107.9 (4)
O14—C14—O15121.1 (5)O24—C24—O25121.5 (5)
C14—O15—C16109.1 (4)C24—O25—C26110.4 (4)
O15—C16—C17102.9 (4)O25—C26—C27102.5 (4)
O15—C16—H16a105.5 (17)O25—C26—H26a106 (2)
O15—C16—H16b105.4 (15)O25—C26—H26b105.2 (16)
C17—C16—H16a118.0 (16)C27—C26—H26a118.9 (18)
C17—C16—H16b114.6 (13)C27—C26—H26b115.3 (18)
H16a—C16—H16b109 (2)H26a—C26—H26b108 (2)
C13—C17—C16102.3 (4)C23—C27—C26102.3 (4)
C13—C17—C18111.3 (4)C23—C27—C28112.8 (4)
C13—C17—H17106.7 (15)C23—C27—H27104.9 (16)
C16—C17—C18119.7 (5)C26—C27—C28119.2 (4)
C16—C17—H17106.0 (14)C26—C27—H27105.7 (16)
C18—C17—H17110.0 (15)C28—C27—H27110.7 (17)
C17—C18—C19111.4 (4)C27—C28—C29111.0 (4)
C17—C18—H18a110.0 (16)C27—C28—H28a112 (2)
C17—C18—H18b109 (2)C27—C28—H28b116 (2)
C19—C18—H18a103.9 (15)C29—C28—H28a105.2 (19)
C19—C18—H18b110 (2)C29—C28—H28b106.8 (16)
H18a—C18—H18b112 (3)H28a—C28—H28b105 (2)
C11—C19—C18121.5 (4)C21—C29—C28123.0 (5)
C11—C19—C110120.3 (4)C21—C29—C210119.6 (5)
C18—C19—C110118.1 (4)C28—C29—C210117.4 (4)
C19—C110—C111118.0 (5)C29—C210—C211119.0 (5)
C19—C110—H110120 (2)C29—C210—H210119 (2)
C111—C110—H110122 (2)C211—C210—H210122 (2)
C110—C111—O111127.2 (5)C210—C211—O211128.9 (5)
C110—C111—C112122.8 (5)C210—C211—C212121.3 (5)
O111—C111—C112110.0 (4)O211—C211—C212109.7 (5)
C111—O111—C114104.8 (4)C211—O211—C214104.2 (4)
C111—C112—O112110.2 (5)C211—C212—O212109.8 (5)
C111—C112—C113121.1 (5)C211—C212—C213121.6 (5)
O112—C112—C113128.6 (5)O212—C212—C213128.6 (5)
C112—O112—C114105.6 (4)C212—O212—C214103.9 (4)
C11—C113—C112118.3 (4)C21—C213—C212118.1 (4)
C11—C113—H113119.0 (18)C21—C213—H213120 (2)
C112—C113—H113122.6 (18)C212—C213—H213121 (2)
O111—C114—O112107.7 (4)O211—C214—O212107.4 (4)
O111—C114—H114a112 (4)O211—C214—H214a108.8 (18)
O111—C114—H114b108 (2)O211—C214—H214b108 (2)
O112—C114—H114a110 (3)O212—C214—H214a99 (2)
O112—C114—H114b111 (3)O212—C214—H214b110 (2)
H114a—C114—H114b109 (4)H214a—C214—H214b122 (3)

Experimental details

Crystal data
Chemical formulaC21H20O8
Mr400.38
Crystal system, space groupTriclinic, 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)
V3)926.8 (2)
Z2
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.20 × 0.10 × 0.05
Data collection
DiffractometerBruker SMART CCD
diffractometer
Absorption correction
No. of measured, independent and
observed (F2 > 2σF2) reflections
10605, 4460, 2592
Rint0.068
(sin θ/λ)max1)0.669
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.044, 1.07
No. of reflections4460
No. of parameters681
No. of restraints3941.12
H-atom treatmentAll H-atom parameters refined
Δρmax, Δρmin (e Å3)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.

 

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