2,3,7,8,12,13-Hexahydr­oxy-10,15-dihydro-5H-tribenzo[a,d,g]cyclo­nonene acetone disolvate

The title compound, C₂₁H₁₈O₆·2C₃H₆O, crystallizes as a clathrate complex that includes two acetone guest mol­ecules in a capsular assembly formed by two 2,3,7,8,12,13-hexa­hydr­oxy-10,15-dihydro-5H-tribenzo[a,d,g]cyclo­nonene mol­ecules. Inter­molecular hydrogen-bonding and host-guest inter­actions define this dimeric clathrate complex, which is also part of a two-dimensional extensively hydrogen-bonded sheet involving the clathrate complex and acetone solvent mol­ecules in the extended crystal packing.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.054
• wR factor = 0.154
• Data-to-parameter ratio = 16.4

checkCIF/PLATON results

No syntax errors found



Alert level B
ABSTM02_ALERT_3_B  The ratio of expected to reported Tmax/Tmin(RR') is < 0.75
            Tmin and Tmax reported:      0.651     1.000
            Tmin(prime) and Tmax expected:      0.957     0.992
            RR(prime) =      0.675
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large .............       0.67

Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.134
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.13
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          3

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

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

---

Computing details

Data collection: COLLECT (Nonius, 1999); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2003) and POV-RAY (Cason, 2002); software used to prepare material for publication: local program.

2,3,7,8,12,13-Hexahydroxy-10,15-dihydro-5H-tribenzo[a,d,g]cyclononene acetone disolvate

Crystal data

C21H18O6·2C3H6O	Z = 2
Mr = 482.51	F(000) = 512
Triclinic, P1	Dx = 1.372 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.6680 (2) Å	Cell parameters from 8798 reflections
b = 11.0804 (3) Å	θ = 1.0–27.5°
c = 11.0992 (3) Å	µ = 0.10 mm^−1
α = 79.924 (1)°	T = 150 K
β = 65.001 (1)°	Block, colourless
γ = 82.157 (2)°	0.43 × 0.23 × 0.08 mm
V = 1167.86 (5) Å^3

Data collection

Nonius KappaCCD area-detector diffractometer	5340 independent reflections
Radiation source: fine-focus sealed tube	2750 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.134
φ and ω scans	θmax = 27.5°, θmin = 2.6°
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	h = −13→13
Tmin = 0.651, Tmax = 1.000	k = −14→14
23276 measured reflections	l = −14→14

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.154	H-atom parameters constrained
S = 0.96	w = 1/[σ^2(Fo^2) + (0.0705P)^2] where P = (Fo^2 + 2Fc^2)/3
5340 reflections	(Δ/σ)max < 0.001
326 parameters	Δρmax = 0.27 e Å^−3
0 restraints	Δρmin = −0.29 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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	0.6400 (2)	0.6928 (2)	0.0359 (2)	0.0266 (5)
C2	0.5430 (2)	0.6033 (2)	0.0942 (2)	0.0286 (5)
H2	0.4521	0.6239	0.0979	0.034*
C3	0.5739 (2)	0.4869 (2)	0.1463 (2)	0.0281 (5)
C4	0.7079 (2)	0.4548 (2)	0.1395 (2)	0.0277 (5)
C5	0.8050 (2)	0.5412 (2)	0.0793 (2)	0.0281 (5)
H5	0.8962	0.5190	0.0740	0.034*
C6	0.7760 (2)	0.6595 (2)	0.0258 (2)	0.0270 (5)
C7	0.8920 (2)	0.7481 (2)	−0.0342 (2)	0.0287 (5)
H7A	0.9797	0.7029	−0.0870	0.034*
H7B	0.8705	0.8141	−0.0967	0.034*
C8	0.9138 (2)	0.8066 (2)	0.0690 (2)	0.0266 (5)
C9	0.9975 (2)	0.7419 (2)	0.1315 (2)	0.0279 (5)
H9	1.0403	0.6638	0.1068	0.034*
C10	1.0196 (2)	0.7887 (2)	0.2279 (2)	0.0275 (5)
C11	0.9608 (2)	0.9050 (2)	0.2616 (2)	0.0275 (5)
C12	0.8808 (2)	0.9705 (2)	0.1983 (2)	0.0271 (5)
H12	0.8426	1.0505	0.2198	0.032*
C13	0.8543 (2)	0.9227 (2)	0.1035 (2)	0.0263 (5)
C14	0.7566 (2)	0.9989 (2)	0.0472 (2)	0.0275 (5)
H14A	0.7700	1.0873	0.0381	0.033*
H14B	0.7785	0.9780	−0.0430	0.033*
C15	0.6071 (2)	0.9750 (2)	0.1382 (2)	0.0259 (5)
C16	0.5469 (2)	1.0316 (2)	0.2543 (2)	0.0266 (5)
H16	0.5991	1.0864	0.2685	0.032*
C17	0.4150 (2)	1.0115 (2)	0.3494 (2)	0.0260 (5)
C18	0.3369 (2)	0.9337 (2)	0.3267 (2)	0.0258 (5)
C19	0.3931 (2)	0.8779 (2)	0.2117 (2)	0.0279 (5)
H19	0.3386	0.8261	0.1966	0.034*
C20	0.5293 (2)	0.8957 (2)	0.1161 (2)	0.0261 (5)
C21	0.5877 (2)	0.8221 (2)	−0.0019 (2)	0.0287 (5)
H21A	0.5147	0.8176	−0.0335	0.034*
H21B	0.6649	0.8648	−0.0765	0.034*
O22	0.48092 (16)	0.39764 (15)	0.20692 (18)	0.0380 (4)
H22	0.4020	0.4272	0.2128	0.046*
O23	0.74473 (16)	0.34100 (15)	0.19177 (17)	0.0348 (4)
H23	0.6730	0.3042	0.2414	0.042*
O24	1.09942 (17)	0.72756 (15)	0.29359 (17)	0.0355 (4)
H24	1.1267	0.6574	0.2694	0.043*
O25	0.98041 (16)	0.95779 (15)	0.35537 (17)	0.0342 (4)
H25	1.0480	0.9203	0.3693	0.041*
O26	0.35380 (16)	1.06163 (16)	0.46696 (16)	0.0336 (4)
H26	0.4028	1.1156	0.4654	0.040*
O27	0.20381 (15)	0.91070 (15)	0.42175 (16)	0.0320 (4)
H27	0.1805	0.9565	0.4817	0.038*
C30	0.3924 (2)	0.6310 (2)	0.4679 (3)	0.0372 (6)
H30A	0.3364	0.6828	0.4252	0.056*
H30B	0.3320	0.5987	0.5596	0.056*
H30C	0.4401	0.5626	0.4166	0.056*
C31	0.4974 (2)	0.7061 (2)	0.4715 (2)	0.0301 (6)
C32	0.6384 (2)	0.7056 (2)	0.3618 (2)	0.0364 (6)
H32A	0.6944	0.7594	0.3771	0.055*
H32B	0.6321	0.7353	0.2759	0.055*
H32C	0.6820	0.6217	0.3599	0.055*
O33	0.46572 (17)	0.76761 (16)	0.56321 (17)	0.0392 (4)
C40	−0.0322 (3)	0.4237 (3)	0.3639 (3)	0.0476 (7)
H40A	−0.0544	0.5127	0.3556	0.071*
H40B	−0.0797	0.3880	0.4576	0.071*
H40C	−0.0629	0.3872	0.3075	0.071*
C41	0.1208 (3)	0.3980 (2)	0.3197 (2)	0.0348 (6)
C42	0.1718 (3)	0.2688 (2)	0.3462 (3)	0.0454 (7)
H42A	0.2711	0.2580	0.2895	0.068*
H42B	0.1214	0.2133	0.3258	0.068*
H42C	0.1567	0.2498	0.4407	0.068*
O43	0.20072 (17)	0.48078 (16)	0.26624 (18)	0.0390 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0300 (13)	0.0268 (13)	0.0255 (13)	−0.0001 (10)	−0.0133 (11)	−0.0060 (10)
C2	0.0239 (12)	0.0319 (14)	0.0325 (14)	0.0011 (10)	−0.0137 (11)	−0.0077 (11)
C3	0.0243 (12)	0.0301 (14)	0.0288 (13)	−0.0047 (10)	−0.0083 (11)	−0.0054 (11)
C4	0.0286 (13)	0.0256 (13)	0.0276 (13)	0.0016 (10)	−0.0112 (11)	−0.0042 (10)
C5	0.0240 (12)	0.0306 (14)	0.0293 (14)	0.0015 (10)	−0.0103 (11)	−0.0074 (11)
C6	0.0286 (13)	0.0311 (14)	0.0217 (13)	−0.0025 (10)	−0.0101 (10)	−0.0044 (10)
C7	0.0255 (12)	0.0309 (14)	0.0259 (13)	−0.0012 (10)	−0.0070 (11)	−0.0040 (11)
C8	0.0216 (12)	0.0288 (13)	0.0254 (13)	−0.0050 (10)	−0.0059 (10)	−0.0008 (10)
C9	0.0234 (12)	0.0249 (13)	0.0325 (14)	−0.0004 (10)	−0.0081 (11)	−0.0056 (11)
C10	0.0206 (12)	0.0311 (14)	0.0301 (14)	−0.0043 (10)	−0.0101 (11)	−0.0010 (11)
C11	0.0214 (12)	0.0309 (14)	0.0284 (13)	−0.0043 (10)	−0.0065 (11)	−0.0066 (11)
C12	0.0235 (12)	0.0232 (13)	0.0327 (14)	−0.0021 (10)	−0.0090 (11)	−0.0054 (10)
C13	0.0200 (11)	0.0291 (14)	0.0252 (13)	−0.0063 (10)	−0.0044 (10)	−0.0011 (10)
C14	0.0283 (12)	0.0248 (13)	0.0269 (13)	−0.0017 (10)	−0.0088 (11)	−0.0034 (10)
C15	0.0256 (12)	0.0237 (13)	0.0269 (13)	0.0019 (10)	−0.0120 (10)	0.0009 (10)
C16	0.0275 (13)	0.0216 (12)	0.0330 (14)	−0.0011 (10)	−0.0149 (11)	−0.0035 (10)
C17	0.0251 (12)	0.0264 (13)	0.0279 (13)	0.0023 (10)	−0.0124 (11)	−0.0060 (10)
C18	0.0218 (12)	0.0263 (13)	0.0299 (14)	0.0011 (10)	−0.0132 (11)	−0.0003 (10)
C19	0.0277 (12)	0.0272 (13)	0.0346 (14)	0.0020 (10)	−0.0188 (11)	−0.0056 (11)
C20	0.0289 (12)	0.0238 (13)	0.0284 (13)	0.0025 (10)	−0.0163 (11)	−0.0015 (10)
C21	0.0293 (13)	0.0315 (14)	0.0278 (13)	0.0002 (10)	−0.0147 (11)	−0.0037 (11)
O22	0.0260 (9)	0.0316 (10)	0.0542 (12)	−0.0024 (7)	−0.0160 (9)	−0.0008 (9)
O23	0.0254 (9)	0.0294 (10)	0.0407 (11)	−0.0006 (7)	−0.0078 (8)	0.0018 (8)
O24	0.0373 (10)	0.0311 (10)	0.0475 (11)	0.0042 (8)	−0.0262 (9)	−0.0104 (8)
O25	0.0285 (9)	0.0397 (11)	0.0419 (11)	0.0039 (7)	−0.0191 (8)	−0.0169 (9)
O26	0.0298 (9)	0.0382 (11)	0.0353 (10)	−0.0038 (7)	−0.0122 (8)	−0.0131 (8)
O27	0.0234 (9)	0.0396 (11)	0.0330 (10)	−0.0013 (7)	−0.0095 (8)	−0.0111 (8)
C30	0.0377 (15)	0.0353 (15)	0.0404 (16)	−0.0068 (12)	−0.0178 (13)	−0.0014 (12)
C31	0.0338 (14)	0.0257 (13)	0.0316 (14)	−0.0020 (10)	−0.0160 (12)	0.0009 (11)
C32	0.0360 (14)	0.0365 (15)	0.0336 (15)	−0.0047 (11)	−0.0104 (12)	−0.0052 (12)
O33	0.0369 (10)	0.0448 (11)	0.0331 (10)	−0.0073 (8)	−0.0081 (8)	−0.0113 (9)
C40	0.0316 (15)	0.0583 (19)	0.0501 (18)	−0.0053 (13)	−0.0152 (14)	−0.0027 (15)
C41	0.0331 (14)	0.0415 (16)	0.0312 (15)	−0.0014 (12)	−0.0144 (12)	−0.0065 (12)
C42	0.0484 (17)	0.0374 (17)	0.0496 (18)	−0.0065 (13)	−0.0205 (15)	0.0007 (13)
O43	0.0325 (10)	0.0349 (11)	0.0493 (12)	−0.0015 (8)	−0.0173 (9)	−0.0037 (9)

Geometric parameters (Å, º)

C1—C2	1.401 (3)	C17—O26	1.369 (3)
C1—C6	1.408 (3)	C17—C18	1.396 (3)
C1—C21	1.520 (3)	C18—C19	1.379 (3)
C2—C3	1.375 (3)	C18—O27	1.390 (3)
C2—H2	0.9500	C19—C20	1.406 (3)
C3—O22	1.373 (3)	C19—H19	0.9500
C3—C4	1.398 (3)	C20—C21	1.521 (3)
C4—O23	1.372 (3)	C21—H21A	0.9900
C4—C5	1.378 (3)	C21—H21B	0.9900
C5—C6	1.392 (3)	O22—H22	0.8400
C5—H5	0.9500	O23—H23	0.8400
C6—C7	1.531 (3)	O24—H24	0.8400
C7—C8	1.521 (3)	O25—H25	0.8400
C7—H7A	0.9900	O26—H26	0.8400
C7—H7B	0.9900	O27—H27	0.8400
C8—C13	1.396 (3)	C30—C31	1.500 (3)
C8—C9	1.403 (3)	C30—H30A	0.9800
C9—C10	1.382 (3)	C30—H30B	0.9800
C9—H9	0.9500	C30—H30C	0.9800
C10—O24	1.382 (3)	C31—O33	1.227 (3)
C10—C11	1.394 (3)	C31—C32	1.482 (3)
C11—O25	1.379 (3)	C32—H32A	0.9800
C11—C12	1.381 (3)	C32—H32B	0.9800
C12—C13	1.398 (3)	C32—H32C	0.9800
C12—H12	0.9500	C40—C41	1.494 (3)
C13—C14	1.522 (3)	C40—H40A	0.9800
C14—C15	1.514 (3)	C40—H40B	0.9800
C14—H14A	0.9900	C40—H40C	0.9800
C14—H14B	0.9900	C41—O43	1.232 (3)
C15—C16	1.393 (3)	C41—C42	1.486 (4)
C15—C20	1.404 (3)	C42—H42A	0.9800
C16—C17	1.375 (3)	C42—H42B	0.9800
C16—H16	0.9500	C42—H42C	0.9800
C2—C1—C6	118.1 (2)	O26—C17—C16	124.61 (19)
C2—C1—C21	117.3 (2)	O26—C17—C18	116.8 (2)
C6—C1—C21	124.4 (2)	C16—C17—C18	118.6 (2)
C3—C2—C1	122.7 (2)	C19—C18—O27	120.24 (19)
C3—C2—H2	118.7	C19—C18—C17	119.9 (2)
C1—C2—H2	118.7	O27—C18—C17	119.8 (2)
O22—C3—C2	124.4 (2)	C18—C19—C20	121.6 (2)
O22—C3—C4	116.4 (2)	C18—C19—H19	119.2
C2—C3—C4	119.2 (2)	C20—C19—H19	119.2
O23—C4—C5	119.4 (2)	C15—C20—C19	118.4 (2)
O23—C4—C3	122.1 (2)	C15—C20—C21	123.2 (2)
C5—C4—C3	118.5 (2)	C19—C20—C21	118.25 (19)
C4—C5—C6	123.2 (2)	C1—C21—C20	111.66 (18)
C4—C5—H5	118.4	C1—C21—H21A	109.3
C6—C5—H5	118.4	C20—C21—H21A	109.3
C5—C6—C1	118.2 (2)	C1—C21—H21B	109.3
C5—C6—C7	118.0 (2)	C20—C21—H21B	109.3
C1—C6—C7	123.7 (2)	H21A—C21—H21B	107.9
C8—C7—C6	114.22 (18)	C3—O22—H22	109.5
C8—C7—H7A	108.7	C4—O23—H23	109.5
C6—C7—H7A	108.7	C10—O24—H24	109.5
C8—C7—H7B	108.7	C11—O25—H25	109.5
C6—C7—H7B	108.7	C17—O26—H26	109.5
H7A—C7—H7B	107.6	C18—O27—H27	109.5
C13—C8—C9	118.6 (2)	C31—C30—H30A	109.5
C13—C8—C7	122.5 (2)	C31—C30—H30B	109.5
C9—C8—C7	118.9 (2)	H30A—C30—H30B	109.5
C10—C9—C8	121.9 (2)	C31—C30—H30C	109.5
C10—C9—H9	119.1	H30A—C30—H30C	109.5
C8—C9—H9	119.1	H30B—C30—H30C	109.5
C9—C10—O24	123.9 (2)	O33—C31—C32	121.0 (2)
C9—C10—C11	119.4 (2)	O33—C31—C30	120.1 (2)
O24—C10—C11	116.70 (19)	C32—C31—C30	118.9 (2)
O25—C11—C12	118.6 (2)	C31—C32—H32A	109.5
O25—C11—C10	122.3 (2)	C31—C32—H32B	109.5
C12—C11—C10	119.1 (2)	H32A—C32—H32B	109.5
C11—C12—C13	122.0 (2)	C31—C32—H32C	109.5
C11—C12—H12	119.0	H32A—C32—H32C	109.5
C13—C12—H12	119.0	H32B—C32—H32C	109.5
C8—C13—C12	119.0 (2)	C41—C40—H40A	109.5
C8—C13—C14	123.3 (2)	C41—C40—H40B	109.5
C12—C13—C14	117.7 (2)	H40A—C40—H40B	109.5
C15—C14—C13	110.69 (18)	C41—C40—H40C	109.5
C15—C14—H14A	109.5	H40A—C40—H40C	109.5
C13—C14—H14A	109.5	H40B—C40—H40C	109.5
C15—C14—H14B	109.5	O43—C41—C42	121.5 (2)
C13—C14—H14B	109.5	O43—C41—C40	121.4 (2)
H14A—C14—H14B	108.1	C42—C41—C40	117.1 (2)
C16—C15—C20	118.7 (2)	C41—C42—H42A	109.5
C16—C15—C14	116.96 (19)	C41—C42—H42B	109.5
C20—C15—C14	124.3 (2)	H42A—C42—H42B	109.5
C17—C16—C15	122.7 (2)	C41—C42—H42C	109.5
C17—C16—H16	118.6	H42A—C42—H42C	109.5
C15—C16—H16	118.6	H42B—C42—H42C	109.5
C6—C1—C2—C3	2.6 (3)	C9—C8—C13—C12	0.4 (3)
C21—C1—C2—C3	−172.6 (2)	C7—C8—C13—C12	−179.3 (2)
C1—C2—C3—O22	178.4 (2)	C9—C8—C13—C14	−177.2 (2)
C1—C2—C3—C4	−1.0 (3)	C7—C8—C13—C14	3.2 (3)
O22—C3—C4—O23	−0.7 (3)	C11—C12—C13—C8	−1.9 (3)
C2—C3—C4—O23	178.7 (2)	C11—C12—C13—C14	175.8 (2)
O22—C3—C4—C5	179.9 (2)	C8—C13—C14—C15	92.5 (3)
C2—C3—C4—C5	−0.7 (3)	C12—C13—C14—C15	−85.1 (2)
O23—C4—C5—C6	−178.8 (2)	C13—C14—C15—C16	77.4 (2)
C3—C4—C5—C6	0.6 (3)	C13—C14—C15—C20	−99.4 (2)
C4—C5—C6—C1	1.0 (3)	C20—C15—C16—C17	1.1 (3)
C4—C5—C6—C7	178.0 (2)	C14—C15—C16—C17	−175.9 (2)
C2—C1—C6—C5	−2.6 (3)	C15—C16—C17—O26	177.5 (2)
C21—C1—C6—C5	172.2 (2)	C15—C16—C17—C18	−1.8 (3)
C2—C1—C6—C7	−179.4 (2)	O26—C17—C18—C19	−178.6 (2)
C21—C1—C6—C7	−4.6 (3)	C16—C17—C18—C19	0.8 (3)
C5—C6—C7—C8	−79.6 (3)	O26—C17—C18—O27	0.0 (3)
C1—C6—C7—C8	97.2 (3)	C16—C17—C18—O27	179.3 (2)
C6—C7—C8—C13	−96.2 (3)	O27—C18—C19—C20	−177.6 (2)
C6—C7—C8—C9	84.2 (3)	C17—C18—C19—C20	1.0 (3)
C13—C8—C9—C10	1.6 (3)	C16—C15—C20—C19	0.6 (3)
C7—C8—C9—C10	−178.8 (2)	C14—C15—C20—C19	177.4 (2)
C8—C9—C10—O24	179.0 (2)	C16—C15—C20—C21	−175.5 (2)
C8—C9—C10—C11	−2.1 (3)	C14—C15—C20—C21	1.2 (3)
C9—C10—C11—O25	−179.0 (2)	C18—C19—C20—C15	−1.6 (3)
O24—C10—C11—O25	0.0 (3)	C18—C19—C20—C21	174.7 (2)
C9—C10—C11—C12	0.5 (3)	C2—C1—C21—C20	85.6 (2)
O24—C10—C11—C12	179.6 (2)	C6—C1—C21—C20	−89.3 (3)
O25—C11—C12—C13	−179.0 (2)	C15—C20—C21—C1	95.1 (3)
C10—C11—C12—C13	1.4 (3)	C19—C20—C21—C1	−81.0 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O22—H22···O43	0.84	2.00	2.831 (2)	168
O23—H23···O33^i	0.84	2.13	2.884 (2)	150
O23—H23···O22	0.84	2.32	2.738 (2)	112
O24—H24···O43^ii	0.84	2.01	2.818 (2)	162
O25—H25···O27^ii	0.84	1.97	2.740 (2)	153
O25—H25···O24	0.84	2.34	2.754 (2)	111
O26—H26···O33^iii	0.84	1.93	2.762 (2)	172
O27—H27···O25^iii	0.84	2.16	2.911 (2)	149
O27—H27···O26	0.84	2.25	2.704 (2)	114

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