(5R,8R)-2-(3,8-Dimethyl-2-oxo-1,2,4,5,6,7,8,8a-octa-hydro-azulen-5-yl)acrylic acid (rupestonic acid).

The title compound, C(15)H(20)O(3), crystallizes with two independent mol-ecules in the asymmetric unit. In both mol-ecules, the seven-membered ring adopts a chair conformation. In the crystal structure, inter-molecular O-H⋯O hydrogen bonds link the mol-ecules into chains extending in the [201] direction. The absolute configuration was assigned on the basis of the starting materials.

Related literature

For related crystal structures, see: Oberti et al. (1983 ▶). For biological activities of sesquiterpenes, see: Endo et al. (1979 ▶); Iguchi et al. (1986 ▶); Kubo et al. (1992 ▶); Delgado et al. (1991 ▶)

Experimental

Crystal data

C15H20O3

M = 248.31

Monoclinic,

a = 9.5295 (19) Å

b = 9.4821 (19) Å

c = 15.047 (3) Å

β = 98.36 (3)°

V = 1345.2 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 (2) K

0.29 × 0.08 × 0.08 mm

Data collection

Rigaku R-AXIS RAPID IP area-detector diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.976, T max = 0.993

13040 measured reflections

3254 independent reflections

2012 reflections with I > 2σ(I)

R int = 0.067

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.111

S = 1.02

3254 reflections

343 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 e Å−3

Δρmin = −0.16 e Å−3

Data collection: RAPID-AUTO (Rigaku, 2004 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808001402/cv2378sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808001402/cv2378Isup2.hkl

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

C15H20O3	F(000) = 536
Mr = 248.31	Dx = 1.226 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 6207 reflections
a = 9.5295 (19) Å	θ = 6.0–55.0°
b = 9.4821 (19) Å	µ = 0.08 mm−1
c = 15.047 (3) Å	T = 293 K
β = 98.36 (3)°	Needle, colorless
V = 1345.2 (5) Å3	0.29 × 0.08 × 0.08 mm
Z = 4

Rigaku R-AXIS RAPID IP area-detector diffractometer	3254 independent reflections
Radiation source: Rotating Anode	2012 reflections with I > 2σ(I)
graphite	Rint = 0.067
ω oscillation scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −12→12
Tmin = 0.976, Tmax = 0.993	k = −11→12
13040 measured reflections	l = −19→19

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0543P)2] where P = (Fo2 + 2Fc2)/3
3254 reflections	(Δ/σ)max < 0.001
343 parameters	Δρmax = 0.14 e Å−3
1 restraint	Δρmin = −0.16 e Å−3

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.

	x	y	z	Uiso*/Ueq
O1	0.1814 (3)	0.3739 (4)	0.2549 (2)	0.1099 (14)
O2	0.1916 (3)	0.4857 (3)	0.12807 (18)	0.0632 (7)
O3	−0.6320 (3)	0.5450 (4)	−0.18584 (17)	0.0883 (11)
O4	1.1007 (3)	0.4719 (3)	0.65333 (19)	0.0753 (8)
O5	1.2819 (3)	0.6146 (4)	0.6438 (2)	0.0726 (8)
O6	0.4647 (2)	0.5556 (3)	0.18400 (17)	0.0685 (8)
C1	0.1251 (4)	0.4058 (4)	0.1813 (3)	0.0539 (10)
C2	−0.0184 (3)	0.3600 (4)	0.1407 (2)	0.0418 (8)
C3	−0.0794 (3)	0.4117 (3)	0.0475 (2)	0.0395 (7)
H3A	−0.0651	0.5140	0.0465	0.047*
C4	−0.2392 (3)	0.3848 (4)	0.0280 (2)	0.0484 (9)
H4A	−0.2538	0.2841	0.0200	0.058*
H4B	−0.2804	0.4122	0.0807	0.058*
C5	−0.3195 (3)	0.4575 (4)	−0.0511 (2)	0.0438 (8)
C6	−0.2531 (3)	0.5444 (4)	−0.1181 (2)	0.0475 (8)
H6A	−0.2052	0.6255	−0.0866	0.057*
C7	−0.1458 (3)	0.4665 (4)	−0.1671 (2)	0.0507 (9)
H7A	−0.1267	0.5285	−0.2161	0.061*
C8	−0.2072 (5)	0.3311 (5)	−0.2112 (3)	0.0745 (12)
H8A	−0.1375	0.2862	−0.2417	0.112*
H8B	−0.2896	0.3529	−0.2536	0.112*
H8C	−0.2331	0.2687	−0.1660	0.112*
C9	−0.0031 (4)	0.4419 (5)	−0.1081 (3)	0.0541 (10)
C10	−0.0028 (4)	0.3477 (4)	−0.0261 (2)	0.0482 (9)
H10A	0.0946	0.3278	−0.0008	0.058*
H10B	−0.0478	0.2588	−0.0452	0.058*
C11	−0.4614 (3)	0.4519 (4)	−0.0694 (2)	0.0515 (9)
C12	−0.5604 (4)	0.3782 (6)	−0.0172 (3)	0.0790 (15)
H12A	−0.5440	0.4097	0.0440	0.118*
H12B	−0.5446	0.2783	−0.0193	0.118*
H12C	−0.6564	0.3989	−0.0428	0.118*
C13	−0.5085 (4)	0.5330 (5)	−0.1502 (2)	0.0579 (10)
C14	−0.3832 (4)	0.5989 (5)	−0.1823 (3)	0.0626 (10)
H14A	−0.3889	0.7009	−0.1797	0.075*
H14B	−0.3775	0.5710	−0.2437	0.075*
C15	1.1608 (3)	0.5541 (4)	0.6110 (2)	0.0511 (9)
C16	1.1042 (3)	0.5984 (4)	0.5178 (2)	0.0458 (8)
C17	0.9465 (3)	0.5744 (4)	0.4913 (2)	0.0415 (8)
H17A	0.9257	0.4770	0.5069	0.050*
C18	0.8648 (3)	0.6722 (4)	0.5459 (2)	0.0510 (9)
H18A	0.9221	0.6884	0.6038	0.061*
H18B	0.8526	0.7623	0.5153	0.061*
C19	0.7194 (3)	0.6196 (5)	0.5620 (2)	0.0545 (9)
H19A	0.7314	0.5273	0.5899	0.065*
H19B	0.6846	0.6824	0.6048	0.065*
C20	0.6060 (3)	0.6081 (4)	0.4799 (2)	0.0484 (8)
H20A	0.5217	0.5698	0.5016	0.058*
C21	0.5632 (4)	0.7506 (5)	0.4404 (3)	0.0631 (11)
H21A	0.5390	0.8116	0.4868	0.095*
H21B	0.4827	0.7403	0.3945	0.095*
H21C	0.6408	0.7907	0.4148	0.095*
C22	0.6444 (3)	0.5018 (4)	0.4090 (2)	0.0458 (8)
H22A	0.6818	0.4149	0.4387	0.055*
C23	0.7508 (3)	0.5621 (3)	0.3543 (2)	0.0390 (7)
C24	0.9026 (3)	0.5920 (4)	0.3903 (2)	0.0450 (8)
H24A	0.9234	0.6881	0.3746	0.054*
H24B	0.9615	0.5304	0.3599	0.054*
C25	0.5173 (3)	0.4672 (5)	0.3372 (2)	0.0571 (9)
H25A	0.5093	0.3662	0.3274	0.069*
H25B	0.4298	0.5016	0.3551	0.069*
C26	0.5476 (3)	0.5405 (4)	0.2543 (2)	0.0501 (9)
C27	0.6940 (3)	0.5903 (4)	0.2692 (2)	0.0422 (8)
C28	0.7624 (4)	0.6651 (4)	0.1996 (3)	0.0598 (10)
H28A	0.8567	0.6293	0.1998	0.090*
H28B	0.7668	0.7643	0.2126	0.090*
H28C	0.7078	0.6500	0.1416	0.090*
C29	−0.0845 (4)	0.2777 (5)	0.1914 (3)	0.0642 (11)
H29A	−0.0407	0.2523	0.2484	0.077*
H29B	−0.1752	0.2448	0.1702	0.077*
C30	1.1901 (4)	0.6522 (5)	0.4661 (3)	0.0745 (14)
H30B	1.2861	0.6625	0.4877	0.089*
H30C	1.1551	0.6801	0.4078	0.089*
H2A	0.281 (6)	0.505 (6)	0.156 (4)	0.13 (2)*
H5A	1.310 (5)	0.600 (5)	0.703 (3)	0.095 (16)*
H9A	0.038 (4)	0.530 (4)	−0.085 (2)	0.053 (10)*
H9B	0.064 (3)	0.408 (3)	−0.146 (2)	0.045 (9)*

	U11	U22	U33	U12	U13	U23
O1	0.071 (2)	0.175 (4)	0.069 (2)	−0.038 (2)	−0.0345 (17)	0.046 (2)
O2	0.0440 (14)	0.0778 (19)	0.0615 (17)	−0.0130 (14)	−0.0139 (13)	0.0067 (15)
O3	0.0444 (15)	0.156 (3)	0.0570 (17)	0.0192 (17)	−0.0173 (12)	0.006 (2)
O4	0.0705 (17)	0.088 (2)	0.0608 (18)	−0.0119 (17)	−0.0140 (14)	0.0196 (17)
O5	0.0468 (15)	0.107 (2)	0.0570 (19)	−0.0091 (15)	−0.0175 (13)	0.0051 (17)
O6	0.0454 (14)	0.098 (2)	0.0551 (17)	−0.0105 (14)	−0.0164 (12)	−0.0039 (16)
C1	0.044 (2)	0.066 (2)	0.048 (2)	0.0027 (18)	−0.0050 (18)	0.002 (2)
C2	0.0367 (17)	0.045 (2)	0.0414 (19)	0.0039 (15)	−0.0034 (14)	0.0019 (16)
C3	0.0309 (16)	0.0446 (18)	0.0411 (19)	0.0009 (13)	−0.0010 (13)	−0.0020 (15)
C4	0.0371 (17)	0.062 (2)	0.043 (2)	−0.0046 (16)	−0.0052 (14)	0.0043 (17)
C5	0.0365 (17)	0.055 (2)	0.0383 (19)	−0.0006 (16)	−0.0010 (14)	−0.0051 (17)
C6	0.0417 (17)	0.051 (2)	0.047 (2)	0.0049 (15)	−0.0006 (15)	0.0064 (17)
C7	0.0506 (19)	0.062 (2)	0.0388 (19)	−0.0016 (18)	0.0026 (15)	0.0049 (18)
C8	0.089 (3)	0.085 (3)	0.046 (2)	0.004 (3)	−0.003 (2)	−0.014 (2)
C9	0.045 (2)	0.069 (3)	0.050 (2)	0.010 (2)	0.0107 (18)	0.004 (2)
C10	0.0398 (17)	0.053 (2)	0.050 (2)	0.0096 (16)	−0.0016 (16)	0.0045 (18)
C11	0.0329 (17)	0.082 (3)	0.0371 (19)	−0.0007 (17)	−0.0021 (14)	−0.0076 (19)
C12	0.040 (2)	0.141 (5)	0.053 (2)	−0.019 (2)	−0.0010 (18)	0.000 (3)
C13	0.0418 (19)	0.084 (3)	0.044 (2)	0.0127 (19)	−0.0054 (16)	−0.004 (2)
C14	0.050 (2)	0.076 (3)	0.057 (2)	0.012 (2)	−0.0069 (17)	0.016 (2)
C15	0.0392 (19)	0.057 (2)	0.052 (2)	0.0039 (17)	−0.0078 (16)	0.003 (2)
C16	0.0329 (15)	0.058 (2)	0.043 (2)	0.0003 (16)	−0.0042 (14)	−0.0023 (17)
C17	0.0320 (15)	0.055 (2)	0.0353 (17)	0.0000 (15)	−0.0033 (13)	−0.0019 (16)
C18	0.0346 (17)	0.067 (2)	0.048 (2)	0.0031 (17)	−0.0060 (15)	−0.0116 (18)
C19	0.0463 (19)	0.075 (3)	0.043 (2)	0.0037 (18)	0.0092 (16)	−0.0038 (18)
C20	0.0329 (16)	0.064 (2)	0.048 (2)	−0.0001 (17)	0.0059 (14)	−0.0020 (18)
C21	0.045 (2)	0.073 (3)	0.072 (3)	0.0121 (19)	0.0091 (19)	−0.001 (2)
C22	0.0365 (16)	0.059 (2)	0.0399 (19)	−0.0068 (15)	−0.0020 (14)	0.0013 (16)
C23	0.0337 (15)	0.0435 (18)	0.0392 (19)	−0.0033 (14)	0.0029 (13)	−0.0046 (15)
C24	0.0333 (15)	0.060 (2)	0.0395 (19)	−0.0020 (16)	−0.0018 (14)	−0.0030 (17)
C25	0.0447 (19)	0.070 (2)	0.055 (2)	−0.0174 (19)	0.0021 (16)	−0.003 (2)
C26	0.0396 (18)	0.056 (2)	0.051 (2)	−0.0045 (16)	−0.0047 (16)	−0.0079 (18)
C27	0.0354 (15)	0.0500 (19)	0.0389 (19)	−0.0004 (15)	−0.0024 (14)	−0.0075 (16)
C28	0.052 (2)	0.078 (3)	0.049 (2)	−0.0049 (19)	0.0043 (17)	0.002 (2)
C29	0.054 (2)	0.080 (3)	0.052 (2)	0.000 (2)	−0.0118 (18)	0.012 (2)
C30	0.0357 (19)	0.128 (4)	0.058 (3)	−0.018 (2)	0.0005 (18)	0.010 (3)

O1—C1	1.197 (4)	C14—H14A	0.9700
O2—C1	1.328 (4)	C14—H14B	0.9700
O2—H2A	0.91 (6)	C15—C16	1.487 (5)
O3—C13	1.225 (4)	C16—C30	1.312 (5)
O4—C15	1.203 (4)	C16—C17	1.515 (4)
O5—C15	1.318 (4)	C17—C24	1.525 (4)
O5—H5A	0.90 (5)	C17—C18	1.526 (4)
O6—C26	1.233 (4)	C17—H17A	0.9800
C1—C2	1.480 (5)	C18—C19	1.524 (5)
C2—C29	1.314 (5)	C18—H18A	0.9700
C2—C3	1.520 (4)	C18—H18B	0.9700
C3—C4	1.530 (4)	C19—C20	1.523 (5)
C3—C10	1.537 (4)	C19—H19A	0.9700
C3—H3A	0.9800	C19—H19B	0.9700
C4—C5	1.487 (4)	C20—C21	1.508 (5)
C4—H4A	0.9700	C20—C22	1.550 (5)
C4—H4B	0.9700	C20—H20A	0.9800
C5—C11	1.341 (4)	C21—H21A	0.9600
C5—C6	1.512 (4)	C21—H21B	0.9600
C6—C7	1.534 (5)	C21—H21C	0.9600
C6—C14	1.545 (5)	C22—C23	1.509 (4)
C6—H6A	0.9800	C22—C25	1.537 (4)
C7—C8	1.522 (6)	C22—H22A	0.9800
C7—C9	1.530 (5)	C23—C27	1.342 (4)
C7—H7A	0.9800	C23—C24	1.496 (4)
C8—H8A	0.9600	C24—H24A	0.9700
C8—H8B	0.9600	C24—H24B	0.9700
C8—H8C	0.9600	C25—C26	1.492 (5)
C9—C10	1.523 (5)	C25—H25A	0.9700
C9—H9A	0.97 (4)	C25—H25B	0.9700
C9—H9B	0.97 (3)	C26—C27	1.459 (4)
C10—H10A	0.9700	C27—C28	1.492 (5)
C10—H10B	0.9700	C28—H28A	0.9600
C11—C13	1.454 (5)	C28—H28B	0.9600
C11—C12	1.486 (5)	C28—H28C	0.9600
C12—H12A	0.9600	C29—H29A	0.9300
C12—H12B	0.9600	C29—H29B	0.9300
C12—H12C	0.9600	C30—H30B	0.9300
C13—C14	1.489 (5)	C30—H30C	0.9300
C1—O2—H2A	109 (3)	O5—C15—C16	114.1 (3)
C15—O5—H5A	115 (3)	C30—C16—C15	119.8 (3)
O1—C1—O2	120.8 (4)	C30—C16—C17	125.6 (3)
O1—C1—C2	124.8 (4)	C15—C16—C17	114.6 (3)
O2—C1—C2	114.3 (3)	C16—C17—C24	111.4 (2)
C29—C2—C1	115.3 (3)	C16—C17—C18	109.3 (3)
C29—C2—C3	125.2 (3)	C24—C17—C18	112.5 (3)
C1—C2—C3	119.5 (3)	C16—C17—H17A	107.8
C2—C3—C4	111.1 (3)	C24—C17—H17A	107.8
C2—C3—C10	112.3 (3)	C18—C17—H17A	107.8
C4—C3—C10	111.1 (3)	C19—C18—C17	115.7 (3)
C2—C3—H3A	107.4	C19—C18—H18A	108.4
C4—C3—H3A	107.4	C17—C18—H18A	108.4
C10—C3—H3A	107.4	C19—C18—H18B	108.4
C5—C4—C3	117.3 (3)	C17—C18—H18B	108.4
C5—C4—H4A	108.0	H18A—C18—H18B	107.4
C3—C4—H4A	108.0	C20—C19—C18	116.7 (3)
C5—C4—H4B	108.0	C20—C19—H19A	108.1
C3—C4—H4B	108.0	C18—C19—H19A	108.1
H4A—C4—H4B	107.2	C20—C19—H19B	108.1
C11—C5—C4	122.2 (3)	C18—C19—H19B	108.1
C11—C5—C6	113.1 (3)	H19A—C19—H19B	107.3
C4—C5—C6	124.8 (3)	C21—C20—C19	112.0 (3)
C5—C6—C7	115.5 (3)	C21—C20—C22	112.9 (3)
C5—C6—C14	102.9 (3)	C19—C20—C22	113.2 (3)
C7—C6—C14	113.0 (3)	C21—C20—H20A	106.0
C5—C6—H6A	108.4	C19—C20—H20A	106.0
C7—C6—H6A	108.4	C22—C20—H20A	106.0
C14—C6—H6A	108.4	C20—C21—H21A	109.5
C8—C7—C9	112.2 (3)	C20—C21—H21B	109.5
C8—C7—C6	112.0 (3)	H21A—C21—H21B	109.5
C9—C7—C6	113.1 (3)	C20—C21—H21C	109.5
C8—C7—H7A	106.3	H21A—C21—H21C	109.5
C9—C7—H7A	106.3	H21B—C21—H21C	109.5
C6—C7—H7A	106.3	C23—C22—C25	102.8 (3)
C7—C8—H8A	109.5	C23—C22—C20	112.0 (3)
C7—C8—H8B	109.5	C25—C22—C20	112.5 (3)
H8A—C8—H8B	109.5	C23—C22—H22A	109.8
C7—C8—H8C	109.5	C25—C22—H22A	109.8
H8A—C8—H8C	109.5	C20—C22—H22A	109.8
H8B—C8—H8C	109.5	C27—C23—C24	122.9 (3)
C10—C9—C7	117.1 (3)	C27—C23—C22	112.7 (3)
C10—C9—H9A	105 (2)	C24—C23—C22	124.4 (3)
C7—C9—H9A	111 (2)	C23—C24—C17	116.9 (3)
C10—C9—H9B	111 (2)	C23—C24—H24A	108.1
C7—C9—H9B	109 (2)	C17—C24—H24A	108.1
H9A—C9—H9B	103 (3)	C23—C24—H24B	108.1
C9—C10—C3	114.0 (3)	C17—C24—H24B	108.1
C9—C10—H10A	108.7	H24A—C24—H24B	107.3
C3—C10—H10A	108.7	C26—C25—C22	105.0 (3)
C9—C10—H10B	108.7	C26—C25—H25A	110.7
C3—C10—H10B	108.7	C22—C25—H25A	110.7
H10A—C10—H10B	107.6	C26—C25—H25B	110.7
C5—C11—C13	109.3 (3)	C22—C25—H25B	110.7
C5—C11—C12	127.4 (3)	H25A—C25—H25B	108.8
C13—C11—C12	123.2 (3)	O6—C26—C27	125.0 (3)
C11—C12—H12A	109.5	O6—C26—C25	126.4 (3)
C11—C12—H12B	109.5	C27—C26—C25	108.6 (3)
H12A—C12—H12B	109.5	C23—C27—C26	109.1 (3)
C11—C12—H12C	109.5	C23—C27—C28	127.4 (3)
H12A—C12—H12C	109.5	C26—C27—C28	123.5 (3)
H12B—C12—H12C	109.5	C27—C28—H28A	109.5
O3—C13—C11	125.1 (3)	C27—C28—H28B	109.5
O3—C13—C14	125.7 (4)	H28A—C28—H28B	109.5
C11—C13—C14	109.2 (3)	C27—C28—H28C	109.5
C13—C14—C6	105.4 (3)	H28A—C28—H28C	109.5
C13—C14—H14A	110.7	H28B—C28—H28C	109.5
C6—C14—H14A	110.7	C2—C29—H29A	120.0
C13—C14—H14B	110.7	C2—C29—H29B	120.0
C6—C14—H14B	110.7	H29A—C29—H29B	120.0
H14A—C14—H14B	108.8	C16—C30—H30B	120.0
O4—C15—O5	122.7 (3)	C16—C30—H30C	120.0
O4—C15—C16	123.1 (3)	H30B—C30—H30C	120.0
O1—C1—C2—C29	−0.4 (6)	O4—C15—C16—C30	−159.5 (4)
O2—C1—C2—C29	178.2 (3)	O5—C15—C16—C30	21.6 (5)
O1—C1—C2—C3	178.2 (4)	O4—C15—C16—C17	20.0 (5)
O2—C1—C2—C3	−3.1 (4)	O5—C15—C16—C17	−159.0 (3)
C29—C2—C3—C4	13.2 (5)	C30—C16—C17—C24	11.7 (5)
C1—C2—C3—C4	−165.3 (3)	C15—C16—C17—C24	−167.7 (3)
C29—C2—C3—C10	−111.9 (4)	C30—C16—C17—C18	−113.2 (4)
C1—C2—C3—C10	69.6 (4)	C15—C16—C17—C18	67.4 (4)
C2—C3—C4—C5	166.6 (3)	C16—C17—C18—C19	−152.4 (3)
C10—C3—C4—C5	−67.6 (4)	C24—C17—C18—C19	83.4 (4)
C3—C4—C5—C11	−173.6 (3)	C17—C18—C19—C20	−66.8 (5)
C3—C4—C5—C6	6.0 (5)	C18—C19—C20—C21	−67.0 (4)
C11—C5—C6—C7	−121.7 (3)	C18—C19—C20—C22	62.1 (4)
C4—C5—C6—C7	58.7 (5)	C21—C20—C22—C23	51.2 (4)
C11—C5—C6—C14	2.0 (4)	C19—C20—C22—C23	−77.3 (4)
C4—C5—C6—C14	−177.7 (3)	C21—C20—C22—C25	−63.9 (4)
C5—C6—C7—C8	53.1 (4)	C19—C20—C22—C25	167.5 (3)
C14—C6—C7—C8	−65.1 (4)	C25—C22—C23—C27	11.9 (4)
C5—C6—C7—C9	−74.9 (4)	C20—C22—C23—C27	−109.1 (3)
C14—C6—C7—C9	167.0 (3)	C25—C22—C23—C24	−169.8 (3)
C8—C7—C9—C10	−64.2 (5)	C20—C22—C23—C24	69.2 (4)
C6—C7—C9—C10	63.7 (5)	C27—C23—C24—C17	171.4 (3)
C7—C9—C10—C3	−68.2 (5)	C22—C23—C24—C17	−6.7 (5)
C2—C3—C10—C9	−150.9 (3)	C16—C17—C24—C23	176.3 (3)
C4—C3—C10—C9	84.1 (4)	C18—C17—C24—C23	−60.6 (4)
C4—C5—C11—C13	179.8 (3)	C23—C22—C25—C26	−13.2 (4)
C6—C5—C11—C13	0.2 (4)	C20—C22—C25—C26	107.4 (3)
C4—C5—C11—C12	0.6 (6)	C22—C25—C26—O6	−169.9 (4)
C6—C5—C11—C12	−179.0 (4)	C22—C25—C26—C27	11.0 (4)
C5—C11—C13—O3	177.8 (4)	C24—C23—C27—C26	176.4 (3)
C12—C11—C13—O3	−3.0 (6)	C22—C23—C27—C26	−5.3 (4)
C5—C11—C13—C14	−2.4 (4)	C24—C23—C27—C28	−5.9 (5)
C12—C11—C13—C14	176.9 (4)	C22—C23—C27—C28	172.4 (3)
O3—C13—C14—C6	−176.7 (4)	O6—C26—C27—C23	177.0 (3)
C11—C13—C14—C6	3.5 (4)	C25—C26—C27—C23	−3.9 (4)
C5—C6—C14—C13	−3.2 (4)	O6—C26—C27—C28	−0.8 (5)
C7—C6—C14—C13	122.1 (3)	C25—C26—C27—C28	178.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O6	0.91 (6)	1.80 (6)	2.699 (4)	166 (5)
O5—H5A···O3i	0.90 (5)	1.76 (5)	2.658 (4)	171 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O6	0.91 (6)	1.80 (6)	2.699 (4)	166 (5)
O5—H5A⋯O3i	0.90 (5)	1.76 (5)	2.658 (4)	171 (5)

Symmetry code: (i) .