Limonin isolated from the seeds of Citrus limetta (Indian sweet lemon)

The title mol­ecule, C₂₆H₃₀O₈ [systematic name: (4aS,14bR)-12-(furan-3-yl)-6,6,8a,12a-tetra­methyl­deca­hydro-1H,3H-oxireno[2,3-d]pyrano[4′,3′:3,3a]isobenzofuro[5,4-f]isochromene-3,8,10(6H,9aH)-trione], commonly known as limonin, is an anti­proliferative polyoxgenated bioactive mol­ecule. It comprises a fused cyclic system containing a cyclo­hexane (D), a cyclo­hexa­none (C), a furan (B), an epoxide and two lactone rings (A and E). In addition to these rings, a second furan ring (F) is present as a substituent. Only the cyclo­hexane (D) ring has a chair conformation; the other six-membered rings (A, C and E) have twist-boat conformations due to steric hinderance or bonding strain. In the crystal, mol­ecules are linked by C—H...O hydrogen bonds, forming a three-dimensional structure.

Key indicators

• Single-crystal X-ray study
• T = 299 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.036
• wR factor = 0.110
• Data-to-parameter ratio = 13.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT934_ALERT_3_B Number of (Iobs-Icalc)/SigmaW > 10 Outliers ....          5 Check

Alert level C
PLAT412_ALERT_2_C Short Intra XH3 .. XHn     H2A    ..  H25B    ..       1.80 Ang.
PLAT412_ALERT_2_C Short Intra XH3 .. XHn     H11    ..  H26B    ..       1.89 Ang.

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details found in the CIF      Please Do !
PLAT432_ALERT_2_G Short Inter X...Y Contact  O4     ..  C17     ..       2.88 Ang.
PLAT791_ALERT_4_G The Model has Chirality at C1      (Chiral SPGR)          R Verify
PLAT791_ALERT_4_G The Model has Chirality at C5      (Chiral SPGR)          S Verify
PLAT791_ALERT_4_G The Model has Chirality at C7      (Chiral SPGR)          R Verify
PLAT791_ALERT_4_G The Model has Chirality at C10     (Chiral SPGR)          R Verify
PLAT791_ALERT_4_G The Model has Chirality at C11     (Chiral SPGR)          R Verify
PLAT791_ALERT_4_G The Model has Chirality at C14     (Chiral SPGR)          S Verify
PLAT791_ALERT_4_G The Model has Chirality at C15     (Chiral SPGR)          R Verify
PLAT791_ALERT_4_G The Model has Chirality at C16     (Chiral SPGR)          S Verify
PLAT791_ALERT_4_G The Model has Chirality at C18     (Chiral SPGR)          S Verify
PLAT899_ALERT_4_G SHELXL97   is Deprecated and Succeeded by SHELXL       2014 Note
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) Still          78 %
PLAT916_ALERT_2_G Hooft y and Flack x Parameter values differ by .       0.18 Check
PLAT916_ALERT_2_G Hooft y and Flack x Parameter values differ by .       0.16 Check

   0 ALERT level A = Most likely a serious problem - resolve or explain
   1 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  15 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
  10 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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Computing details

Data collection: CAD-4-PC Software (Enraf–Nonius, 1996); cell refinement: CAD-4-PC Software (Enraf–Nonius, 1996); data reduction: REDU4 (Stoe & Cie, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

(4aS,14bR)-12-(Furan-3-yl)-6,6,8a,12a-tetramethyldecahydro-1H,3H-oxireno[2,3-d]pyrano[4',3':3,3a]isobenzofuro[5,4-f]isochromene-3,8,10(6H,9aH)-trione

Crystal data

C26H30O8	Dx = 1.365 Mg m^−3
Mr = 470.50	Melting point: 320 K
Orthorhombic, P212121	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 8.877 (1) Å	θ = 5.6–20.1°
b = 14.533 (2) Å	µ = 0.84 mm^−1
c = 17.748 (2) Å	T = 299 K
V = 2289.7 (5) Å^3	Prism, colourless
Z = 4	0.28 × 0.22 × 0.15 mm
F(000) = 1000

Data collection

Enraf–Nonius CAD-4 diffractometer	Rint = 0.018
Radiation source: fine-focus sealed tube	θmax = 67.0°, θmin = 3.9°
Graphite monochromator	h = −10→10
ω/2θ scans	k = −17→1
5062 measured reflections	l = −21→1
4081 independent reflections	3 standard reflections every 120 min
3659 reflections with I > 2σ(I)	intensity decay: 1.0%

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.036	w = 1/[σ^2(Fo^2) + (0.0611P)^2 + 0.4711P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.110	(Δ/σ)max = 0.001
S = 1.10	Δρmax = 0.20 e Å^−3
4081 reflections	Δρmin = −0.14 e Å^−3
308 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0025 (3)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983); 1742 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.2 (2)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.6003 (2)	0.80012 (14)	0.33749 (12)	0.0269 (4)
C2	0.5523 (3)	0.73683 (17)	0.40261 (13)	0.0351 (5)
H2A	0.4863	0.7715	0.4357	0.042*
H2B	0.4935	0.6867	0.3817	0.042*
C3	0.7945 (3)	0.66158 (18)	0.41522 (15)	0.0435 (6)
C4	0.8133 (3)	0.68083 (16)	0.33300 (13)	0.0381 (6)
H4A	0.7519	0.6387	0.3038	0.046*
H4B	0.9177	0.6722	0.3185	0.046*
C5	0.7656 (2)	0.77923 (16)	0.31750 (13)	0.0308 (5)
H5	0.7855	0.7952	0.2648	0.037*
C6	0.7664 (3)	0.91464 (17)	0.39612 (14)	0.0380 (6)
C7	0.6193 (2)	0.90414 (15)	0.35240 (13)	0.0301 (5)
H7	0.6422	0.9299	0.3027	0.036*
C8	0.4757 (3)	0.95437 (16)	0.37654 (14)	0.0339 (5)
H8A	0.4382	0.9291	0.4235	0.041*
H8B	0.4961	1.0193	0.3838	0.041*
C9	0.3599 (3)	0.94112 (16)	0.31414 (13)	0.0333 (5)
C10	0.3312 (2)	0.84126 (15)	0.28916 (12)	0.0291 (5)
C11	0.4883 (2)	0.79615 (14)	0.27056 (12)	0.0260 (4)
H11	0.5325	0.8381	0.2334	0.031*
C12	0.4600 (3)	0.70816 (15)	0.22574 (12)	0.0313 (5)
H12A	0.3807	0.6723	0.2493	0.038*
H12B	0.5507	0.6710	0.2241	0.038*
C13	0.4129 (3)	0.73613 (16)	0.14529 (13)	0.0324 (5)
H13A	0.3583	0.6854	0.1226	0.039*
H13B	0.5030	0.7464	0.1156	0.039*
C14	0.3128 (2)	0.82416 (14)	0.14136 (12)	0.0277 (4)
C15	0.2343 (2)	0.83565 (15)	0.21743 (13)	0.0289 (5)
C16	0.0807 (3)	0.87401 (17)	0.21645 (14)	0.0356 (5)
H16	0.0484	0.9054	0.2626	0.043*
C17	0.0162 (3)	0.90980 (17)	0.14487 (15)	0.0392 (5)
C18	0.1886 (2)	0.80715 (16)	0.08166 (13)	0.0317 (5)
H18	0.1360	0.7500	0.0945	0.038*
C19	0.2444 (2)	0.79965 (17)	0.00200 (13)	0.0334 (5)
C20	0.2693 (3)	0.7219 (2)	−0.03703 (14)	0.0429 (6)
H20	0.2550	0.6629	−0.0181	0.051*
C21	0.3232 (3)	0.8340 (2)	−0.11317 (15)	0.0474 (6)
H21	0.3533	0.8663	−0.1558	0.057*
C22	0.2793 (3)	0.87306 (19)	−0.04913 (14)	0.0449 (6)
H22	0.2725	0.9358	−0.0394	0.054*
C23	0.8507 (3)	1.0017 (2)	0.37485 (19)	0.0556 (8)
H23A	0.7888	1.0543	0.3855	0.067*
H23B	0.8744	1.0003	0.3221	0.067*
H23C	0.9421	1.0055	0.4035	0.067*
C24	0.7532 (3)	0.9063 (2)	0.48154 (15)	0.0520 (7)
H24A	0.7134	0.8469	0.4943	0.062*
H24B	0.6871	0.9534	0.5002	0.062*
H24C	0.8510	0.9135	0.5039	0.062*
C25	0.2427 (3)	0.79570 (18)	0.35395 (13)	0.0373 (5)
H25A	0.1498	0.8282	0.3617	0.045*
H25B	0.3017	0.7977	0.3992	0.045*
H25C	0.2214	0.7328	0.3412	0.045*
C26	0.4005 (3)	0.91202 (16)	0.12044 (13)	0.0352 (5)
H26A	0.4466	0.9042	0.0719	0.042*
H26B	0.4771	0.9232	0.1575	0.042*
H26C	0.3325	0.9634	0.1188	0.042*
O1	0.6722 (2)	0.69751 (13)	0.44804 (9)	0.0437 (4)
O2	0.85351 (17)	0.83682 (12)	0.36687 (10)	0.0387 (4)
O3	0.07834 (18)	0.88186 (12)	0.07995 (10)	0.0396 (4)
O4	0.3184 (2)	0.74096 (14)	−0.10816 (10)	0.0492 (5)
O5	0.8815 (3)	0.62005 (18)	0.45340 (13)	0.0760 (8)
O6	0.2971 (2)	1.00559 (12)	0.28523 (11)	0.0510 (5)
O7	0.10294 (17)	0.77602 (11)	0.22248 (9)	0.0362 (4)
O8	−0.0850 (2)	0.96443 (15)	0.14442 (12)	0.0605 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0224 (10)	0.0306 (11)	0.0277 (10)	0.0021 (9)	−0.0003 (8)	−0.0015 (9)
C2	0.0297 (11)	0.0435 (13)	0.0322 (12)	0.0020 (10)	−0.0006 (9)	0.0040 (10)
C3	0.0466 (14)	0.0428 (13)	0.0411 (14)	0.0106 (12)	−0.0133 (12)	−0.0042 (11)
C4	0.0320 (12)	0.0407 (13)	0.0415 (13)	0.0111 (10)	−0.0066 (10)	−0.0083 (11)
C5	0.0252 (10)	0.0383 (12)	0.0290 (11)	0.0011 (9)	−0.0015 (9)	−0.0037 (10)
C6	0.0277 (11)	0.0408 (13)	0.0456 (14)	0.0019 (10)	−0.0039 (10)	−0.0119 (11)
C7	0.0264 (10)	0.0334 (11)	0.0304 (11)	0.0005 (9)	0.0017 (9)	−0.0050 (9)
C8	0.0324 (11)	0.0347 (12)	0.0346 (12)	0.0045 (9)	0.0007 (10)	−0.0097 (9)
C9	0.0286 (11)	0.0347 (12)	0.0367 (12)	0.0059 (9)	0.0052 (10)	−0.0042 (10)
C10	0.0229 (10)	0.0333 (11)	0.0311 (11)	0.0024 (9)	0.0044 (9)	−0.0016 (9)
C11	0.0231 (9)	0.0294 (10)	0.0256 (10)	0.0016 (9)	−0.0002 (8)	0.0033 (9)
C12	0.0307 (11)	0.0291 (11)	0.0340 (11)	0.0024 (9)	−0.0024 (9)	−0.0026 (10)
C13	0.0290 (11)	0.0362 (11)	0.0319 (11)	0.0055 (9)	−0.0026 (9)	−0.0036 (9)
C14	0.0224 (10)	0.0317 (11)	0.0291 (11)	0.0018 (9)	0.0000 (9)	0.0022 (9)
C15	0.0225 (10)	0.0299 (11)	0.0342 (12)	−0.0001 (9)	0.0016 (9)	0.0031 (9)
C16	0.0244 (11)	0.0456 (13)	0.0367 (12)	0.0051 (10)	0.0002 (10)	−0.0022 (11)
C17	0.0260 (11)	0.0446 (13)	0.0470 (14)	0.0032 (10)	−0.0019 (10)	0.0012 (12)
C18	0.0257 (10)	0.0361 (11)	0.0333 (11)	0.0001 (9)	−0.0016 (9)	0.0040 (9)
C19	0.0268 (10)	0.0425 (12)	0.0308 (11)	0.0030 (10)	−0.0062 (9)	0.0044 (10)
C20	0.0473 (14)	0.0503 (15)	0.0311 (12)	0.0024 (12)	−0.0012 (11)	0.0058 (11)
C21	0.0476 (14)	0.0596 (16)	0.0349 (13)	0.0010 (13)	−0.0020 (12)	0.0113 (12)
C22	0.0501 (15)	0.0464 (14)	0.0380 (14)	0.0011 (12)	−0.0050 (12)	0.0090 (12)
C23	0.0387 (14)	0.0449 (15)	0.083 (2)	−0.0059 (12)	−0.0018 (15)	−0.0158 (15)
C24	0.0479 (15)	0.0638 (18)	0.0444 (15)	0.0069 (14)	−0.0124 (12)	−0.0194 (13)
C25	0.0262 (10)	0.0519 (14)	0.0339 (11)	0.0020 (11)	0.0029 (10)	0.0050 (11)
C26	0.0316 (11)	0.0386 (13)	0.0353 (12)	−0.0048 (10)	0.0001 (10)	0.0045 (10)
O1	0.0458 (9)	0.0531 (10)	0.0321 (8)	0.0094 (9)	−0.0067 (8)	0.0054 (8)
O2	0.0231 (7)	0.0424 (9)	0.0505 (10)	0.0022 (7)	−0.0053 (7)	−0.0140 (8)
O3	0.0308 (8)	0.0491 (10)	0.0391 (9)	0.0090 (8)	−0.0037 (7)	0.0060 (8)
O4	0.0526 (11)	0.0624 (12)	0.0326 (9)	0.0133 (10)	0.0019 (8)	−0.0004 (8)
O5	0.0822 (16)	0.0946 (17)	0.0512 (12)	0.0491 (15)	−0.0201 (12)	0.0015 (12)
O6	0.0601 (12)	0.0371 (9)	0.0557 (11)	0.0131 (9)	−0.0180 (10)	−0.0032 (9)
O7	0.0242 (7)	0.0445 (9)	0.0398 (9)	−0.0063 (7)	0.0002 (7)	0.0057 (8)
O8	0.0461 (11)	0.0700 (14)	0.0656 (13)	0.0286 (11)	−0.0029 (10)	0.0012 (11)

Geometric parameters (Å, º)

C1—C2	1.537 (3)	C13—H13A	0.9700
C1—C5	1.540 (3)	C13—H13B	0.9700
C1—C7	1.544 (3)	C14—C15	1.529 (3)
C1—C11	1.550 (3)	C14—C26	1.541 (3)
C2—O1	1.453 (3)	C14—C18	1.549 (3)
C2—H2A	0.9700	C15—O7	1.455 (3)
C2—H2B	0.9700	C15—C16	1.473 (3)
C3—O5	1.192 (3)	C16—O7	1.442 (3)
C3—O1	1.338 (3)	C16—C17	1.488 (3)
C3—C4	1.495 (4)	C16—H16	0.9800
C4—C5	1.517 (3)	C17—O8	1.199 (3)
C4—H4A	0.9700	C17—O3	1.341 (3)
C4—H4B	0.9700	C18—O3	1.462 (3)
C5—O2	1.441 (3)	C18—C19	1.502 (3)
C5—H5	0.9800	C18—H18	0.9800
C6—O2	1.465 (3)	C19—C20	1.344 (4)
C6—C23	1.517 (4)	C19—C22	1.434 (3)
C6—C24	1.525 (4)	C20—O4	1.364 (3)
C6—C7	1.526 (3)	C20—H20	0.9300
C7—C8	1.531 (3)	C21—C22	1.329 (4)
C7—H7	0.9800	C21—O4	1.356 (3)
C8—C9	1.523 (3)	C21—H21	0.9300
C8—H8A	0.9700	C22—H22	0.9300
C8—H8B	0.9700	C23—H23A	0.9600
C9—O6	1.205 (3)	C23—H23B	0.9600
C9—C10	1.539 (3)	C23—H23C	0.9600
C10—C15	1.539 (3)	C24—H24A	0.9600
C10—C25	1.542 (3)	C24—H24B	0.9600
C10—C11	1.576 (3)	C24—H24C	0.9600
C11—C12	1.527 (3)	C25—H25A	0.9600
C11—H11	0.9800	C25—H25B	0.9600
C12—C13	1.542 (3)	C25—H25C	0.9600
C12—H12A	0.9700	C26—H26A	0.9600
C12—H12B	0.9700	C26—H26B	0.9600
C13—C14	1.559 (3)	C26—H26C	0.9600
C2—C1—C5	108.63 (18)	C14—C13—H13B	108.7
C2—C1—C7	119.16 (18)	H13A—C13—H13B	107.6
C5—C1—C7	97.37 (17)	C15—C14—C26	110.65 (18)
C2—C1—C11	112.09 (17)	C15—C14—C18	107.29 (17)
C5—C1—C11	115.28 (17)	C26—C14—C18	109.09 (17)
C7—C1—C11	103.77 (16)	C15—C14—C13	108.06 (18)
O1—C2—C1	116.69 (18)	C26—C14—C13	113.74 (18)
O1—C2—H2A	108.1	C18—C14—C13	107.77 (17)
C1—C2—H2A	108.1	O7—C15—C16	58.99 (14)
O1—C2—H2B	108.1	O7—C15—C14	110.77 (18)
C1—C2—H2B	108.1	C16—C15—C14	116.94 (19)
H2A—C2—H2B	107.3	O7—C15—C10	115.37 (18)
O5—C3—O1	118.4 (3)	C16—C15—C10	120.47 (19)
O5—C3—C4	125.3 (3)	C14—C15—C10	118.79 (17)
O1—C3—C4	116.3 (2)	O7—C16—C15	59.90 (14)
C3—C4—C5	108.80 (19)	O7—C16—C17	117.5 (2)
C3—C4—H4A	109.9	C15—C16—C17	119.9 (2)
C5—C4—H4A	109.9	O7—C16—H16	116.0
C3—C4—H4B	109.9	C15—C16—H16	116.0
C5—C4—H4B	109.9	C17—C16—H16	116.0
H4A—C4—H4B	108.3	O8—C17—O3	120.2 (2)
O2—C5—C4	106.62 (18)	O8—C17—C16	121.7 (2)
O2—C5—C1	105.16 (17)	O3—C17—C16	118.0 (2)
C4—C5—C1	114.23 (19)	O3—C18—C19	104.78 (17)
O2—C5—H5	110.2	O3—C18—C14	111.85 (18)
C4—C5—H5	110.2	C19—C18—C14	114.90 (18)
C1—C5—H5	110.2	O3—C18—H18	108.4
O2—C6—C23	107.2 (2)	C19—C18—H18	108.4
O2—C6—C24	109.4 (2)	C14—C18—H18	108.4
C23—C6—C24	110.5 (2)	C20—C19—C22	105.3 (2)
O2—C6—C7	101.20 (17)	C20—C19—C18	126.9 (2)
C23—C6—C7	112.2 (2)	C22—C19—C18	127.8 (2)
C24—C6—C7	115.6 (2)	C19—C20—O4	111.0 (2)
C6—C7—C8	121.51 (18)	C19—C20—H20	124.5
C6—C7—C1	106.18 (18)	O4—C20—H20	124.5
C8—C7—C1	115.07 (18)	C22—C21—O4	111.2 (2)
C6—C7—H7	104.0	C22—C21—H21	124.4
C8—C7—H7	104.0	O4—C21—H21	124.4
C1—C7—H7	104.0	C21—C22—C19	106.7 (3)
C9—C8—C7	107.36 (18)	C21—C22—H22	126.7
C9—C8—H8A	110.2	C19—C22—H22	126.7
C7—C8—H8A	110.2	C6—C23—H23A	109.5
C9—C8—H8B	110.2	C6—C23—H23B	109.5
C7—C8—H8B	110.2	H23A—C23—H23B	109.5
H8A—C8—H8B	108.5	C6—C23—H23C	109.5
O6—C9—C8	121.6 (2)	H23A—C23—H23C	109.5
O6—C9—C10	122.3 (2)	H23B—C23—H23C	109.5
C8—C9—C10	116.13 (19)	C6—C24—H24A	109.5
C9—C10—C15	112.40 (18)	C6—C24—H24B	109.5
C9—C10—C25	105.94 (18)	H24A—C24—H24B	109.5
C15—C10—C25	108.01 (18)	C6—C24—H24C	109.5
C9—C10—C11	107.82 (17)	H24A—C24—H24C	109.5
C15—C10—C11	107.42 (17)	H24B—C24—H24C	109.5
C25—C10—C11	115.37 (18)	C10—C25—H25A	109.5
C12—C11—C1	122.43 (17)	C10—C25—H25B	109.5
C12—C11—C10	108.15 (17)	H25A—C25—H25B	109.5
C1—C11—C10	113.04 (16)	C10—C25—H25C	109.5
C12—C11—H11	103.7	H25A—C25—H25C	109.5
C1—C11—H11	103.7	H25B—C25—H25C	109.5
C10—C11—H11	103.7	C14—C26—H26A	109.5
C11—C12—C13	107.83 (17)	C14—C26—H26B	109.5
C11—C12—H12A	110.1	H26A—C26—H26B	109.5
C13—C12—H12A	110.1	C14—C26—H26C	109.5
C11—C12—H12B	110.1	H26A—C26—H26C	109.5
C13—C12—H12B	110.1	H26B—C26—H26C	109.5
H12A—C12—H12B	108.5	C3—O1—C2	120.44 (19)
C12—C13—C14	114.34 (18)	C5—O2—C6	112.20 (16)
C12—C13—H13A	108.7	C17—O3—C18	118.86 (18)
C14—C13—H13A	108.7	C21—O4—C20	105.9 (2)
C12—C13—H13B	108.7	C16—O7—C15	61.11 (14)
C5—C1—C2—O1	20.7 (3)	C26—C14—C15—C16	89.4 (2)
C7—C1—C2—O1	−89.3 (3)	C18—C14—C15—C16	−29.5 (3)
C11—C1—C2—O1	149.30 (19)	C13—C14—C15—C16	−145.5 (2)
O5—C3—C4—C5	−138.2 (3)	C26—C14—C15—C10	−68.8 (2)
O1—C3—C4—C5	39.2 (3)	C18—C14—C15—C10	172.33 (18)
C3—C4—C5—O2	55.3 (2)	C13—C14—C15—C10	56.4 (2)
C3—C4—C5—C1	−60.4 (3)	C9—C10—C15—O7	−127.9 (2)
C2—C1—C5—O2	−87.3 (2)	C25—C10—C15—O7	−11.4 (3)
C7—C1—C5—O2	36.9 (2)	C11—C10—C15—O7	113.65 (19)
C11—C1—C5—O2	145.95 (18)	C9—C10—C15—C16	−60.4 (3)
C2—C1—C5—C4	29.2 (2)	C25—C10—C15—C16	56.1 (3)
C7—C1—C5—C4	153.43 (18)	C11—C10—C15—C16	−178.84 (19)
C11—C1—C5—C4	−97.5 (2)	C9—C10—C15—C14	97.0 (2)
O2—C6—C7—C8	164.4 (2)	C25—C10—C15—C14	−146.51 (19)
C23—C6—C7—C8	−81.6 (3)	C11—C10—C15—C14	−21.5 (3)
C24—C6—C7—C8	46.4 (3)	C14—C15—C16—O7	99.1 (2)
O2—C6—C7—C1	30.4 (2)	C10—C15—C16—O7	−103.1 (2)
C23—C6—C7—C1	144.3 (2)	O7—C15—C16—C17	−106.4 (2)
C24—C6—C7—C1	−87.6 (2)	C14—C15—C16—C17	−7.2 (3)
C2—C1—C7—C6	74.7 (2)	C10—C15—C16—C17	150.5 (2)
C5—C1—C7—C6	−41.4 (2)	O7—C16—C17—O8	133.0 (3)
C11—C1—C7—C6	−159.81 (17)	C15—C16—C17—O8	−157.7 (2)
C2—C1—C7—C8	−62.7 (3)	O7—C16—C17—O3	−49.5 (3)
C5—C1—C7—C8	−178.88 (19)	C15—C16—C17—O3	19.8 (3)
C11—C1—C7—C8	62.8 (2)	C15—C14—C18—O3	57.3 (2)
C6—C7—C8—C9	170.9 (2)	C26—C14—C18—O3	−62.6 (2)
C1—C7—C8—C9	−58.7 (3)	C13—C14—C18—O3	173.45 (17)
C7—C8—C9—O6	−126.2 (2)	C15—C14—C18—C19	176.59 (18)
C7—C8—C9—C10	52.3 (3)	C26—C14—C18—C19	56.7 (2)
O6—C9—C10—C15	8.4 (3)	C13—C14—C18—C19	−67.3 (2)
C8—C9—C10—C15	−170.14 (18)	O3—C18—C19—C20	−137.6 (2)
O6—C9—C10—C25	−109.3 (3)	C14—C18—C19—C20	99.3 (3)
C8—C9—C10—C25	72.1 (2)	O3—C18—C19—C22	41.0 (3)
O6—C9—C10—C11	126.6 (2)	C14—C18—C19—C22	−82.2 (3)
C8—C9—C10—C11	−51.9 (2)	C22—C19—C20—O4	0.6 (3)
C2—C1—C11—C12	−62.9 (2)	C18—C19—C20—O4	179.4 (2)
C5—C1—C11—C12	62.1 (3)	O4—C21—C22—C19	0.6 (3)
C7—C1—C11—C12	167.29 (19)	C20—C19—C22—C21	−0.7 (3)
C2—C1—C11—C10	69.3 (2)	C18—C19—C22—C21	−179.5 (2)
C5—C1—C11—C10	−165.73 (18)	O5—C3—O1—C2	−170.9 (3)
C7—C1—C11—C10	−60.5 (2)	C4—C3—O1—C2	11.6 (3)
C9—C10—C11—C12	−164.55 (17)	C1—C2—O1—C3	−44.8 (3)
C15—C10—C11—C12	−43.2 (2)	C4—C5—O2—C6	−142.4 (2)
C25—C10—C11—C12	77.3 (2)	C1—C5—O2—C6	−20.8 (2)
C9—C10—C11—C1	56.6 (2)	C23—C6—O2—C5	−123.5 (2)
C15—C10—C11—C1	177.98 (17)	C24—C6—O2—C5	116.6 (2)
C25—C10—C11—C1	−61.5 (2)	C7—C6—O2—C5	−5.8 (2)
C1—C11—C12—C13	−151.99 (19)	O8—C17—O3—C18	−172.6 (2)
C10—C11—C12—C13	73.9 (2)	C16—C17—O3—C18	9.8 (3)
C11—C12—C13—C14	−36.6 (2)	C19—C18—O3—C17	−175.0 (2)
C12—C13—C14—C15	−23.7 (2)	C14—C18—O3—C17	−49.9 (3)
C12—C13—C14—C26	99.6 (2)	C22—C21—O4—C20	−0.2 (3)
C12—C13—C14—C18	−139.37 (19)	C19—C20—O4—C21	−0.3 (3)
C26—C14—C15—O7	154.24 (17)	C17—C16—O7—C15	110.4 (2)
C18—C14—C15—O7	35.3 (2)	C14—C15—O7—C16	−109.7 (2)
C13—C14—C15—O7	−80.6 (2)	C10—C15—O7—C16	111.7 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O5^i	0.97	2.35	3.313 (3)	171
C4—H4A···O6^ii	0.97	2.54	3.442 (3)	156
C21—H21···O6^iii	0.93	2.52	3.135 (3)	124

Symmetry codes: (i) x−1/2, −y+3/2, −z+1; (ii) −x+1, y−1/2, −z+1/2; (iii) −x+1/2, −y+2, z−1/2.