Absolute configuration of isovouacapenol C.

The title compound, C(27)H(34)O(5) {systematic name: (4aR,5R,6R,6aS,7R,11aS,11bR)-4a,6-dihy-droxy-4,4,7,11b-tetra-methyl-1,2,3,4,4a,5,6,6a,7,11,11a,11b-dodeca-hydro-phenanthro[3,2-b]furan-5-yl benzoate}, is a cassane furan-oditerpene, which was isolated from the roots of Caesalpinia pulcherrima. The three cyclo-hexane rings are trans fused: two of these are in chair conformations with the third in a twisted half-chair conformation, whereas the furan ring is almost planar (r.m.s. deviation = 0.003 Å). An intra-molecular C-H⋯O inter-action generates an S(6) ring. The absolute configurations of the stereogenic centres at positions 4a, 5, 6, 6a, 7, 11a and 11b are R, R, R, S, R, S and R, respectively. In the crystal, mol-ecules are linked into infinite chains along [010] by O-H⋯O hydrogen bonds. C⋯O [3.306 (2)-3.347 (2) Å] short contacts and C-H⋯π inter-actions also occur.

Related literature

For ring conformations, see: Cremer & Pople (1975 ▶). For bond-length data, see: Allen et al. (1987 ▶). For background to plants in Caesalpiniaceae, cassane furan­oditerpenes and their activities, see: Che et al. (1986 ▶); Jiang et al. (2001 ▶); Patil et al. (1997 ▶); Promsawan et al. (2003 ▶); Ragasa et al. (2002 ▶); Smitinand & Larson (2001 ▶); Tewtrakul et al. (2003 ▶). For related structures, see: Jiang et al. (2001 ▶). For the stability of the temperature controller used in the data collection, see Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C27H34O5

M = 438.54

Monoclinic,

a = 11.6236 (7) Å

b = 8.0871 (5) Å

c = 12.4193 (7) Å

β = 98.194 (3)°

V = 1155.51 (12) Å3

Z = 2

Cu Kα radiation

μ = 0.69 mm−1

T = 100 K

0.40 × 0.26 × 0.16 mm

Data collection

Bruker APEX DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.772, T max = 0.896

23749 measured reflections

3328 independent reflections

3237 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.077

S = 1.05

3328 reflections

289 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.26 e Å−3

Absolute structure: Flack (1983 ▶), 1365 Friedel pairs

Flack parameter: 0.07 (17)

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810028023/hb5551sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810028023/hb5551Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C27H34O5	F(000) = 472
Mr = 438.54	Dx = 1.260 Mg m−3
Monoclinic, P21	Melting point = 389–391 K
Hall symbol: P 2yb	Cu Kα radiation, λ = 1.54178 Å
a = 11.6236 (7) Å	Cell parameters from 3328 reflections
b = 8.0871 (5) Å	θ = 3.6–63.0°
c = 12.4193 (7) Å	µ = 0.69 mm−1
β = 98.194 (3)°	T = 100 K
V = 1155.51 (12) Å3	Block, colorless
Z = 2	0.40 × 0.26 × 0.16 mm

Bruker APEX DUO CCD diffractometer	3328 independent reflections
Radiation source: sealed tube	3237 reflections with I > 2σ(I)
graphite	Rint = 0.037
φ and ω scans	θmax = 63.0°, θmin = 3.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→13
Tmin = 0.772, Tmax = 0.896	k = −9→7
23749 measured reflections	l = −14→13

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.077	w = 1/[σ2(Fo2) + (0.0405P)2 + 0.2626P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
3328 reflections	Δρmax = 0.26 e Å−3
289 parameters	Δρmin = −0.26 e Å−3
1 restraint	Absolute structure: Flack (1983), 1365 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.07 (17)

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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.

	x	y	z	Uiso*/Ueq
O1	0.72763 (10)	0.79601 (16)	0.98396 (10)	0.0293 (3)
O2	1.00416 (11)	0.14126 (17)	0.87430 (10)	0.0289 (3)
H1O2	1.074 (2)	0.170 (3)	0.8862 (19)	0.053 (8)*
O3	0.77060 (10)	0.12442 (16)	0.64968 (9)	0.0277 (3)
O4	0.73247 (15)	−0.1497 (2)	0.63427 (14)	0.0558 (5)
O5	0.65515 (11)	0.06283 (18)	0.82285 (11)	0.0305 (3)
H1O5	0.666 (2)	−0.039 (4)	0.839 (2)	0.064 (9)*
C1	1.05196 (15)	0.4722 (2)	0.79744 (15)	0.0294 (4)
H1A	1.0406	0.5910	0.7942	0.035*
H1B	1.0862	0.4444	0.8711	0.035*
C2	1.13691 (16)	0.4242 (3)	0.71969 (17)	0.0366 (5)
H2A	1.1075	0.4634	0.6472	0.044*
H2B	1.2111	0.4775	0.7426	0.044*
C3	1.15455 (16)	0.2376 (3)	0.71644 (17)	0.0362 (5)
H3A	1.1915	0.2007	0.7873	0.043*
H3B	1.2066	0.2125	0.6642	0.043*
C4	1.04021 (15)	0.1404 (3)	0.68549 (15)	0.0290 (4)
C5	0.95342 (15)	0.1960 (2)	0.76622 (14)	0.0248 (4)
C6	0.83929 (14)	0.0968 (2)	0.75469 (14)	0.0246 (4)
H6A	0.8589	−0.0210	0.7607	0.030*
C7	0.76787 (14)	0.1395 (2)	0.84429 (13)	0.0241 (4)
H7A	0.8081	0.0951	0.9129	0.029*
C8	0.74771 (14)	0.3233 (2)	0.85970 (14)	0.0218 (4)
H8A	0.6980	0.3625	0.7943	0.026*
C9	0.86259 (14)	0.4231 (2)	0.86921 (14)	0.0225 (4)
H9A	0.9111	0.3876	0.9363	0.027*
C10	0.93235 (15)	0.3867 (2)	0.77260 (14)	0.0239 (4)
C11	0.84125 (15)	0.6107 (2)	0.87951 (15)	0.0274 (4)
H11A	0.9126	0.6649	0.9112	0.033*
H11B	0.8171	0.6578	0.8080	0.033*
C12	0.74973 (14)	0.6380 (2)	0.94925 (14)	0.0251 (4)
C13	0.67533 (14)	0.5290 (2)	0.98321 (15)	0.0237 (4)
C14	0.67929 (15)	0.3493 (2)	0.95730 (14)	0.0250 (4)
H14A	0.5992	0.3129	0.9341	0.030*
C15	0.60120 (15)	0.6225 (2)	1.04398 (14)	0.0288 (4)
H15A	0.5411	0.5813	1.0783	0.035*
C16	0.63540 (16)	0.7802 (3)	1.04160 (16)	0.0313 (4)
H16A	0.6015	0.8674	1.0744	0.038*
C17	0.72635 (18)	0.2509 (2)	1.05976 (15)	0.0336 (5)
H17A	0.6865	0.2843	1.1188	0.050*
H17B	0.8080	0.2718	1.0785	0.050*
H17C	0.7139	0.1350	1.0461	0.050*
C18	1.06580 (18)	−0.0460 (3)	0.69936 (17)	0.0389 (5)
H18A	1.1315	−0.0740	0.6641	0.058*
H18B	0.9992	−0.1080	0.6672	0.058*
H18C	1.0826	−0.0720	0.7754	0.058*
C19	1.00152 (17)	0.1669 (3)	0.56272 (15)	0.0369 (5)
H19A	1.0538	0.1099	0.5223	0.055*
H19B	1.0024	0.2830	0.5465	0.055*
H19C	0.9243	0.1245	0.5430	0.055*
C20	0.86451 (16)	0.4592 (2)	0.66677 (14)	0.0273 (4)
H20A	0.8826	0.5745	0.6617	0.041*
H20B	0.7826	0.4463	0.6678	0.041*
H20C	0.8863	0.4017	0.6051	0.041*
C21	0.72050 (17)	−0.0116 (3)	0.59848 (17)	0.0360 (5)
C22	0.65118 (16)	0.0302 (3)	0.49182 (17)	0.0376 (5)
C23	0.63903 (19)	0.1895 (3)	0.45270 (17)	0.0479 (6)
H23A	0.6747	0.2767	0.4935	0.058*
C24	0.5734 (2)	0.2196 (4)	0.35231 (19)	0.0622 (5)
H24A	0.5638	0.3268	0.3255	0.075*
C25	0.5217 (2)	0.0850 (4)	0.2917 (2)	0.0622 (5)
H25A	0.4782	0.1041	0.2240	0.075*
C26	0.5340 (2)	−0.0717 (4)	0.33011 (19)	0.0622 (5)
H26A	0.4992	−0.1592	0.2891	0.075*
C27	0.59853 (17)	−0.1005 (3)	0.43053 (18)	0.0481 (6)
H27A	0.6069	−0.2078	0.4574	0.058*

	U11	U22	U33	U12	U13	U23
O1	0.0331 (6)	0.0197 (7)	0.0365 (7)	−0.0005 (5)	0.0095 (5)	−0.0016 (5)
O2	0.0268 (7)	0.0338 (8)	0.0243 (6)	0.0014 (6)	−0.0022 (5)	0.0040 (6)
O3	0.0287 (6)	0.0291 (7)	0.0236 (6)	−0.0015 (5)	−0.0019 (5)	−0.0036 (5)
O4	0.0678 (11)	0.0314 (11)	0.0606 (10)	−0.0050 (8)	−0.0172 (8)	−0.0079 (8)
O5	0.0286 (7)	0.0240 (8)	0.0393 (8)	−0.0063 (5)	0.0060 (6)	0.0004 (6)
C1	0.0276 (9)	0.0312 (12)	0.0305 (10)	−0.0040 (8)	0.0079 (8)	−0.0014 (8)
C2	0.0291 (9)	0.0439 (14)	0.0392 (12)	−0.0084 (9)	0.0130 (8)	−0.0051 (9)
C3	0.0263 (9)	0.0469 (14)	0.0369 (11)	0.0003 (9)	0.0097 (8)	−0.0052 (9)
C4	0.0288 (9)	0.0301 (11)	0.0288 (9)	0.0044 (8)	0.0065 (7)	−0.0029 (8)
C5	0.0248 (9)	0.0301 (11)	0.0185 (9)	0.0028 (7)	−0.0005 (7)	0.0022 (7)
C6	0.0281 (9)	0.0213 (11)	0.0232 (9)	−0.0003 (7)	−0.0010 (7)	−0.0006 (7)
C7	0.0243 (8)	0.0217 (10)	0.0252 (9)	−0.0029 (7)	−0.0002 (7)	0.0013 (8)
C8	0.0229 (8)	0.0207 (10)	0.0218 (9)	0.0000 (7)	0.0026 (7)	0.0023 (7)
C9	0.0234 (8)	0.0242 (10)	0.0194 (8)	−0.0011 (7)	0.0016 (6)	0.0020 (7)
C10	0.0251 (9)	0.0263 (11)	0.0211 (9)	−0.0026 (7)	0.0058 (7)	0.0006 (7)
C11	0.0306 (9)	0.0247 (11)	0.0281 (9)	−0.0065 (8)	0.0092 (7)	0.0004 (8)
C12	0.0266 (9)	0.0224 (10)	0.0257 (9)	0.0011 (8)	0.0016 (7)	0.0002 (8)
C13	0.0220 (9)	0.0233 (11)	0.0255 (9)	0.0016 (7)	0.0027 (7)	0.0019 (7)
C14	0.0220 (8)	0.0250 (11)	0.0282 (9)	−0.0036 (7)	0.0043 (7)	0.0006 (8)
C15	0.0246 (8)	0.0290 (12)	0.0337 (10)	0.0013 (8)	0.0074 (7)	0.0017 (8)
C16	0.0300 (9)	0.0266 (12)	0.0393 (11)	0.0047 (8)	0.0117 (8)	−0.0020 (8)
C17	0.0486 (11)	0.0251 (12)	0.0291 (10)	0.0025 (8)	0.0127 (9)	0.0047 (8)
C18	0.0398 (11)	0.0367 (13)	0.0405 (12)	0.0101 (9)	0.0069 (9)	−0.0042 (9)
C19	0.0415 (11)	0.0432 (14)	0.0281 (10)	0.0028 (9)	0.0129 (8)	−0.0046 (9)
C20	0.0358 (10)	0.0246 (11)	0.0228 (9)	−0.0011 (8)	0.0088 (7)	0.0029 (7)
C21	0.0319 (10)	0.0379 (14)	0.0370 (11)	−0.0010 (9)	0.0011 (8)	−0.0091 (10)
C22	0.0247 (9)	0.0591 (16)	0.0285 (10)	0.0002 (9)	0.0020 (8)	−0.0113 (10)
C23	0.0408 (12)	0.0675 (19)	0.0327 (12)	0.0012 (11)	−0.0042 (9)	−0.0043 (11)
C24	0.0404 (7)	0.1039 (14)	0.0392 (8)	0.0010 (8)	−0.0052 (6)	−0.0099 (8)
C25	0.0404 (7)	0.1039 (14)	0.0392 (8)	0.0010 (8)	−0.0052 (6)	−0.0099 (8)
C26	0.0404 (7)	0.1039 (14)	0.0392 (8)	0.0010 (8)	−0.0052 (6)	−0.0099 (8)
C27	0.0267 (10)	0.0698 (18)	0.0466 (13)	−0.0034 (10)	0.0011 (9)	−0.0195 (12)

O1—C16	1.377 (2)	C11—C12	1.481 (2)
O1—C12	1.384 (2)	C11—H11A	0.9700
O2—C5	1.456 (2)	C11—H11B	0.9700
O2—H1O2	0.84 (3)	C12—C13	1.344 (3)
O3—C21	1.359 (2)	C13—C15	1.438 (3)
O3—C6	1.446 (2)	C13—C14	1.490 (3)
O4—C21	1.203 (3)	C14—C17	1.534 (3)
O5—C7	1.440 (2)	C14—H14A	0.9800
O5—H1O5	0.85 (3)	C15—C16	1.338 (3)
C1—C2	1.526 (2)	C15—H15A	0.9300
C1—C10	1.544 (2)	C16—H16A	0.9300
C1—H1A	0.9700	C17—H17A	0.9600
C1—H1B	0.9700	C17—H17B	0.9600
C2—C3	1.524 (3)	C17—H17C	0.9600
C2—H2A	0.9700	C18—H18A	0.9600
C2—H2B	0.9700	C18—H18B	0.9600
C3—C4	1.545 (3)	C18—H18C	0.9600
C3—H3A	0.9700	C19—H19A	0.9600
C3—H3B	0.9700	C19—H19B	0.9600
C4—C18	1.541 (3)	C19—H19C	0.9600
C4—C19	1.542 (3)	C20—H20A	0.9600
C4—C5	1.586 (2)	C20—H20B	0.9600
C5—C6	1.539 (2)	C20—H20C	0.9600
C5—C10	1.565 (3)	C21—C22	1.488 (3)
C6—C7	1.520 (2)	C22—C23	1.377 (3)
C6—H6A	0.9800	C22—C27	1.392 (3)
C7—C8	1.522 (3)	C23—C24	1.387 (3)
C7—H7A	0.9800	C23—H23A	0.9300
C8—C9	1.550 (2)	C24—C25	1.409 (4)
C8—C14	1.556 (2)	C24—H24A	0.9300
C8—H8A	0.9800	C25—C26	1.355 (4)
C9—C11	1.546 (3)	C25—H25A	0.9300
C9—C10	1.569 (2)	C26—C27	1.381 (3)
C9—H9A	0.9800	C26—H26A	0.9300
C10—C20	1.548 (2)	C27—H27A	0.9300
C16—O1—C12	105.61 (14)	C12—C11—H11B	109.8
C5—O2—H1O2	109.4 (17)	C9—C11—H11B	109.8
C21—O3—C6	116.21 (15)	H11A—C11—H11B	108.2
C7—O5—H1O5	105.5 (18)	C13—C12—O1	110.58 (15)
C2—C1—C10	113.90 (15)	C13—C12—C11	129.30 (17)
C2—C1—H1A	108.8	O1—C12—C11	120.04 (15)
C10—C1—H1A	108.8	C12—C13—C15	106.26 (16)
C2—C1—H1B	108.8	C12—C13—C14	122.06 (16)
C10—C1—H1B	108.8	C15—C13—C14	131.68 (16)
H1A—C1—H1B	107.7	C13—C14—C17	110.19 (15)
C3—C2—C1	111.70 (17)	C13—C14—C8	109.57 (14)
C3—C2—H2A	109.3	C17—C14—C8	114.49 (15)
C1—C2—H2A	109.3	C13—C14—H14A	107.4
C3—C2—H2B	109.3	C17—C14—H14A	107.4
C1—C2—H2B	109.3	C8—C14—H14A	107.4
H2A—C2—H2B	107.9	C16—C15—C13	106.71 (16)
C2—C3—C4	113.34 (16)	C16—C15—H15A	126.6
C2—C3—H3A	108.9	C13—C15—H15A	126.6
C4—C3—H3A	108.9	C15—C16—O1	110.84 (16)
C2—C3—H3B	108.9	C15—C16—H16A	124.6
C4—C3—H3B	108.9	O1—C16—H16A	124.6
H3A—C3—H3B	107.7	C14—C17—H17A	109.5
C18—C4—C19	105.75 (16)	C14—C17—H17B	109.5
C18—C4—C3	108.93 (16)	H17A—C17—H17B	109.5
C19—C4—C3	107.13 (16)	C14—C17—H17C	109.5
C18—C4—C5	109.68 (16)	H17A—C17—H17C	109.5
C19—C4—C5	117.61 (15)	H17B—C17—H17C	109.5
C3—C4—C5	107.49 (15)	C4—C18—H18A	109.5
O2—C5—C6	99.09 (14)	C4—C18—H18B	109.5
O2—C5—C10	107.37 (14)	H18A—C18—H18B	109.5
C6—C5—C10	112.28 (14)	C4—C18—H18C	109.5
O2—C5—C4	106.62 (13)	H18A—C18—H18C	109.5
C6—C5—C4	114.27 (15)	H18B—C18—H18C	109.5
C10—C5—C4	115.46 (15)	C4—C19—H19A	109.5
O3—C6—C7	109.65 (13)	C4—C19—H19B	109.5
O3—C6—C5	111.17 (14)	H19A—C19—H19B	109.5
C7—C6—C5	111.53 (14)	C4—C19—H19C	109.5
O3—C6—H6A	108.1	H19A—C19—H19C	109.5
C7—C6—H6A	108.1	H19B—C19—H19C	109.5
C5—C6—H6A	108.1	C10—C20—H20A	109.5
O5—C7—C6	110.15 (14)	C10—C20—H20B	109.5
O5—C7—C8	106.96 (14)	H20A—C20—H20B	109.5
C6—C7—C8	115.08 (14)	C10—C20—H20C	109.5
O5—C7—H7A	108.1	H20A—C20—H20C	109.5
C6—C7—H7A	108.1	H20B—C20—H20C	109.5
C8—C7—H7A	108.1	O4—C21—O3	124.00 (18)
C7—C8—C9	111.82 (13)	O4—C21—C22	124.02 (19)
C7—C8—C14	109.57 (14)	O3—C21—C22	111.97 (19)
C9—C8—C14	113.63 (13)	C23—C22—C27	120.2 (2)
C7—C8—H8A	107.2	C23—C22—C21	122.82 (19)
C9—C8—H8A	107.2	C27—C22—C21	117.0 (2)
C14—C8—H8A	107.2	C22—C23—C24	119.8 (2)
C11—C9—C8	111.75 (14)	C22—C23—H23A	120.1
C11—C9—C10	110.75 (14)	C24—C23—H23A	120.1
C8—C9—C10	112.18 (14)	C23—C24—C25	118.9 (3)
C11—C9—H9A	107.3	C23—C24—H24A	120.6
C8—C9—H9A	107.3	C25—C24—H24A	120.6
C10—C9—H9A	107.3	C26—C25—C24	121.3 (2)
C1—C10—C20	109.58 (15)	C26—C25—H25A	119.4
C1—C10—C5	107.96 (14)	C24—C25—H25A	119.4
C20—C10—C5	113.24 (15)	C25—C26—C27	119.5 (3)
C1—C10—C9	108.18 (14)	C25—C26—H26A	120.2
C20—C10—C9	108.77 (14)	C27—C26—H26A	120.2
C5—C10—C9	108.99 (14)	C26—C27—C22	120.4 (3)
C12—C11—C9	109.39 (14)	C26—C27—H27A	119.8
C12—C11—H11A	109.8	C22—C27—H27A	119.8
C9—C11—H11A	109.8
C10—C1—C2—C3	−55.8 (2)	C6—C5—C10—C9	56.19 (18)
C1—C2—C3—C4	56.5 (2)	C4—C5—C10—C9	−170.43 (13)
C2—C3—C4—C18	−172.61 (16)	C11—C9—C10—C1	62.08 (18)
C2—C3—C4—C19	73.4 (2)	C8—C9—C10—C1	−172.31 (14)
C2—C3—C4—C5	−53.8 (2)	C11—C9—C10—C20	−56.87 (18)
C18—C4—C5—O2	52.99 (19)	C8—C9—C10—C20	68.74 (18)
C19—C4—C5—O2	173.81 (17)	C11—C9—C10—C5	179.23 (13)
C3—C4—C5—O2	−65.30 (19)	C8—C9—C10—C5	−55.16 (18)
C18—C4—C5—C6	−55.39 (19)	C8—C9—C11—C12	38.72 (19)
C19—C4—C5—C6	65.4 (2)	C10—C9—C11—C12	164.58 (13)
C3—C4—C5—C6	−173.68 (15)	C16—O1—C12—C13	0.04 (18)
C18—C4—C5—C10	172.14 (15)	C16—O1—C12—C11	177.07 (15)
C19—C4—C5—C10	−67.0 (2)	C9—C11—C12—C13	−13.3 (3)
C3—C4—C5—C10	53.85 (19)	C9—C11—C12—O1	170.25 (14)
C21—O3—C6—C7	−99.22 (17)	O1—C12—C13—C15	−0.31 (19)
C21—O3—C6—C5	136.98 (16)	C11—C12—C13—C15	−176.98 (17)
O2—C5—C6—O3	−178.22 (14)	O1—C12—C13—C14	179.95 (15)
C10—C5—C6—O3	68.69 (18)	C11—C12—C13—C14	3.3 (3)
C4—C5—C6—O3	−65.27 (18)	C12—C13—C14—C17	108.18 (19)
O2—C5—C6—C7	59.06 (17)	C15—C13—C14—C17	−71.5 (2)
C10—C5—C6—C7	−54.03 (19)	C12—C13—C14—C8	−18.7 (2)
C4—C5—C6—C7	172.01 (15)	C15—C13—C14—C8	161.67 (17)
O3—C6—C7—O5	48.39 (19)	C7—C8—C14—C13	171.36 (14)
C5—C6—C7—O5	171.97 (14)	C9—C8—C14—C13	45.48 (19)
O3—C6—C7—C8	−72.59 (18)	C7—C8—C14—C17	47.00 (19)
C5—C6—C7—C8	50.99 (19)	C9—C8—C14—C17	−78.89 (19)
O5—C7—C8—C9	−172.92 (13)	C12—C13—C15—C16	0.5 (2)
C6—C7—C8—C9	−50.21 (18)	C14—C13—C15—C16	−179.83 (19)
O5—C7—C8—C14	60.18 (16)	C13—C15—C16—O1	−0.4 (2)
C6—C7—C8—C14	−177.12 (13)	C12—O1—C16—C15	0.3 (2)
C7—C8—C9—C11	177.36 (14)	C6—O3—C21—O4	−1.7 (3)
C14—C8—C9—C11	−57.96 (18)	C6—O3—C21—C22	179.54 (14)
C7—C8—C9—C10	52.30 (18)	O4—C21—C22—C23	−179.9 (2)
C14—C8—C9—C10	176.98 (14)	O3—C21—C22—C23	−1.1 (3)
C2—C1—C10—C20	−71.1 (2)	O4—C21—C22—C27	−0.6 (3)
C2—C1—C10—C5	52.7 (2)	O3—C21—C22—C27	178.17 (17)
C2—C1—C10—C9	170.49 (16)	C27—C22—C23—C24	0.5 (3)
O2—C5—C10—C1	65.60 (17)	C21—C22—C23—C24	179.76 (19)
C6—C5—C10—C1	173.47 (14)	C22—C23—C24—C25	−0.8 (3)
C4—C5—C10—C1	−53.14 (18)	C23—C24—C25—C26	0.6 (4)
O2—C5—C10—C20	−172.90 (13)	C24—C25—C26—C27	0.0 (4)
C6—C5—C10—C20	−65.02 (18)	C25—C26—C27—C22	−0.3 (3)
C4—C5—C10—C20	68.36 (18)	C23—C22—C27—C26	0.1 (3)
O2—C5—C10—C9	−51.69 (17)	C21—C22—C27—C26	−179.21 (19)

Cg1 is the centroid of the C12–C16/O1 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O5—H1O5···O1i	0.85 (2)	2.27 (3)	2.9814 (19)	141 (2)
C19—H19C···O3	0.96	2.37	3.052 (2)	128
C3—H3A···Cg1ii	0.97	2.86	3.805 (2)	166

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C12–C16/O1 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H1O5⋯O1i	0.85 (2)	2.27 (3)	2.9814 (19)	141 (2)
C19—H19C⋯O3	0.96	2.37	3.052 (2)	128
C3—H3A⋯Cg1ii	0.97	2.86	3.805 (2)	166

Symmetry codes: (i) ; (ii) .