Methyl 2-(3a,8a-dimethyl-4-oxodeca-hydro-azulen-6-yl)acrylate.

The title compound, C(16)H(24)O(3), was synthesized from ilicic acid, which was isolated from the aerial part of Inula viscosa- (L) Aiton [or Dittrichia viscosa- (L) Greuter]. The asymmetric unit contains two independent mol-ecules, in each of which the seven-membered ring shows a chair conformation, whereas the five-membered ring presents disorder. In the two molecules, three C atoms in the five-membered ring are disordered over two positions with site-occupancy factors of 0.53/0.47 and 0.83/0.17. The dihedral angle between the two rings is different in the two mol-ecules [31.7 (3) and 47.7 (7)°]. The crystal structure is stabilized by weak inter-molecular C-H⋯O hydrogen-bond inter-actions.

Related literature

For background to the medicinal inter­est in Inula viscosa­ (L) Aiton [or Dittrichia viscosa­ (L) Greuter], see: Shtacher & Kasshman (1970 ▶); Chiappini et al. (1982 ▶); Azoulay et al. (1986 ▶); Bohlman et al. (1977 ▶); Ceccherelli et al. (1988 ▶); Geissman & Toribio (1967 ▶). For conformational analysis, see: Cremer & Pople (1975 ▶). For a related synthesis, see: Barrero et al. (2009 ▶).

Experimental

Crystal data

C16H24O3

M = 264.35

Monoclinic,

a = 6.6954 (3) Å

b = 6.9447 (3) Å

c = 31.6168 (18) Å

β = 90.095 (7)°

V = 1470.10 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 180 K

0.33 × 0.23 × 0.15 mm

Data collection

Agilent Xcalibur Eos Gemini ultra diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.843, T max = 1.000

9032 measured reflections

5575 independent reflections

4990 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.110

S = 1.06

5575 reflections

356 parameters

19 restraints

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶) and ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶ and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811029928/om2451sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811029928/om2451Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811029928/om2451Isup3.cml

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

C16H24O3	F(000) = 576
Mr = 264.35	Dx = 1.194 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: P 2yb	Cell parameters from 3361 reflections
a = 6.6954 (3) Å	θ = 3.6–29.2°
b = 6.9447 (3) Å	µ = 0.08 mm−1
c = 31.6168 (18) Å	T = 180 K
β = 90.095 (7)°	Block, colourless
V = 1470.10 (12) Å3	0.33 × 0.23 × 0.15 mm
Z = 4

Agilent Xcalibur Eos Gemini ultra diffractometer	5575 independent reflections
Radiation source: Enhance (Mo) X-ray Source	4990 reflections with I > 2σ(I)
graphite	Rint = 0.020
Detector resolution: 16.1978 pixels mm-1	θmax = 26.4°, θmin = 3.6°
ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −8→8
Tmin = 0.843, Tmax = 1.000	l = −36→39
9032 measured reflections

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.058P)2 + 0.0579P] where P = (Fo2 + 2Fc2)/3
5575 reflections	(Δ/σ)max = 0.011
356 parameters	Δρmax = 0.14 e Å−3
19 restraints	Δρmin = −0.19 e Å−3

Experimental. The crystal is twinned by pseudo-merohedry. The unit cell is monoclinic but it emulates an orthorhombic P 21 21 2 cell.Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. CrysAlisPro (Agilent,2010)

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O11	−0.3396 (6)	0.7937 (7)	0.78385 (10)	0.0491 (9)
O12	−0.1779 (6)	0.7707 (7)	0.72197 (8)	0.0441 (9)
O13	0.0462 (8)	0.4408 (6)	0.90038 (11)	0.0603 (11)
C11	0.0245 (7)	0.7490 (7)	0.83087 (10)	0.0320 (10)
H11	−0.1000	0.6868	0.8397	0.038*
C12	0.1966 (8)	0.6169 (6)	0.84329 (11)	0.0370 (11)
H12A	0.3233	0.6815	0.8388	0.044*
H12B	0.1943	0.5008	0.8262	0.044*
C13	0.1702 (9)	0.5650 (7)	0.89132 (14)	0.0376 (11)
C16	0.0506 (8)	0.9418 (7)	0.90041 (11)	0.0344 (10)
H16A	0.0105	1.0672	0.9109	0.041*
H16B	−0.0453	0.8491	0.9111	0.041*
C17	0.0323 (8)	0.9457 (7)	0.85143 (11)	0.0371 (11)
H17A	−0.0878	1.0159	0.8439	0.045*
H17B	0.1453	1.0158	0.8400	0.045*
C14	0.2954 (9)	0.6686 (7)	0.92227 (13)	0.0375 (11)
C15	0.2545 (8)	0.8936 (7)	0.91989 (13)	0.0365 (11)
C18A	0.2343 (11)	0.9472 (10)	0.96834 (13)	0.068 (2)	0.53
H18A	0.3233	1.0532	0.9750	0.082*	0.53
H18B	0.0986	0.9879	0.9743	0.082*	0.53
C19A	0.2859 (15)	0.7758 (13)	0.99513 (19)	0.0438 (13)	0.53
H19A	0.2078	0.7746	1.0210	0.053*	0.53
H19B	0.4267	0.7756	1.0024	0.053*	0.53
C20A	0.2344 (11)	0.6059 (9)	0.96745 (13)	0.0562 (16)	0.53
H20A	0.0926	0.5778	0.9688	0.067*	0.53
H20B	0.3082	0.4924	0.9761	0.067*	0.53
C18B	0.2343 (11)	0.9472 (10)	0.96834 (13)	0.068 (2)	0.47
H18C	0.3638	0.9789	0.9802	0.082*	0.47
H18D	0.1462	1.0569	0.9719	0.082*	0.47
C19B	0.1550 (14)	0.7852 (12)	0.9882 (2)	0.0438 (13)	0.47
H19C	0.0105	0.7874	0.9861	0.053*	0.47
H19D	0.1911	0.7858	1.0179	0.053*	0.47
C20B	0.2344 (11)	0.6059 (9)	0.96745 (13)	0.0562 (16)	0.47
H20C	0.1324	0.5068	0.9664	0.067*	0.47
H20D	0.3488	0.5565	0.9828	0.067*	0.47
C111	0.0153 (7)	0.7762 (8)	0.78377 (12)	0.0350 (10)
C112	0.1773 (8)	0.7999 (10)	0.75949 (14)	0.0527 (14)
H11A	0.1632	0.8188	0.7305	0.063*
H11B	0.3039	0.7974	0.7716	0.063*
C113	−0.1814 (7)	0.7805 (8)	0.76432 (12)	0.0340 (10)
C114	−0.3611 (8)	0.7761 (8)	0.69985 (12)	0.0453 (11)
H11C	−0.4307	0.8930	0.7066	0.068*
H11D	−0.4413	0.6676	0.7079	0.068*
H11E	−0.3359	0.7715	0.6700	0.068*
C141	0.5147 (9)	0.6146 (9)	0.91621 (15)	0.0562 (16)
H14A	0.5558	0.6476	0.8880	0.084*
H14B	0.5311	0.4786	0.9205	0.084*
H14C	0.5951	0.6835	0.9363	0.084*
C151	0.4187 (10)	1.0125 (9)	0.90107 (18)	0.0537 (15)
H15A	0.3809	1.1459	0.9015	0.081*
H15B	0.4417	0.9726	0.8724	0.081*
H15C	0.5386	0.9954	0.9173	0.081*
O21	−0.3368 (5)	0.2891 (7)	0.71830 (9)	0.0455 (8)
O22	−0.1755 (6)	0.3099 (7)	0.78059 (8)	0.0435 (8)
O23	0.0557 (8)	0.6369 (6)	0.60233 (12)	0.0710 (13)
C21	0.0213 (7)	0.3281 (7)	0.67099 (11)	0.0336 (10)
H21	−0.1050	0.3890	0.6628	0.040*
C22	0.1921 (8)	0.4596 (6)	0.65588 (14)	0.0435 (12)
H22A	0.1943	0.5748	0.6732	0.052*
H22B	0.3183	0.3933	0.6598	0.052*
C23	0.1736 (7)	0.5141 (6)	0.61251 (15)	0.0367 (10)
C26	0.0504 (8)	0.1303 (7)	0.60083 (14)	0.0422 (11)
H26A	−0.0491	0.2194	0.5902	0.051*
H26B	0.0119	0.0029	0.5913	0.051*
C27	0.0351 (8)	0.1312 (7)	0.64743 (13)	0.0423 (12)
H27A	0.1503	0.0631	0.6585	0.051*
H27B	−0.0820	0.0565	0.6551	0.051*
C24	0.2925 (8)	0.4082 (7)	0.57727 (13)	0.0343 (10)
C25	0.2532 (7)	0.1810 (6)	0.57876 (14)	0.0364 (11)
C28A	0.2445 (10)	0.1255 (7)	0.53289 (15)	0.0547 (15)	0.83
H28A	0.3450	0.0283	0.5271	0.066*	0.83
H28B	0.1146	0.0707	0.5266	0.066*	0.83
C29A	0.2795 (15)	0.2957 (12)	0.50553 (16)	0.0775 (19)	0.83
H29A	0.4178	0.3013	0.4965	0.093*	0.83
H29B	0.1943	0.2918	0.4807	0.093*	0.83
C30A	0.2296 (11)	0.4625 (8)	0.53251 (15)	0.0566 (17)	0.83
H30A	0.0874	0.4888	0.5314	0.068*	0.83
H30B	0.3010	0.5763	0.5231	0.068*	0.83
C28B	0.2445 (10)	0.1255 (7)	0.53289 (15)	0.0547 (15)	0.17
H28C	0.3776	0.1080	0.5214	0.066*	0.17
H28D	0.1693	0.0073	0.5291	0.066*	0.17
C29B	0.143 (5)	0.289 (3)	0.5125 (7)	0.0775 (19)	0.17
H29C	0.1674	0.2891	0.4822	0.093*	0.17
H29D	−0.0002	0.2830	0.5173	0.093*	0.17
C30B	0.2296 (11)	0.4625 (8)	0.53251 (15)	0.0566 (17)	0.17
H30C	0.1315	0.5653	0.5333	0.068*	0.17
H30D	0.3443	0.5067	0.5165	0.068*	0.17
C211	0.0190 (7)	0.3028 (7)	0.71832 (11)	0.0325 (10)
C212	0.1757 (7)	0.2744 (9)	0.74169 (12)	0.0445 (12)
H21A	0.3016	0.2685	0.7293	0.053*
H21B	0.1621	0.2601	0.7708	0.053*
C213	−0.1856 (7)	0.2982 (7)	0.73821 (13)	0.0333 (9)
C214	−0.3691 (8)	0.2993 (11)	0.80196 (13)	0.0582 (15)
H21C	−0.4298	0.1767	0.7963	0.087*
H21D	−0.4542	0.4003	0.7917	0.087*
H21E	−0.3503	0.3138	0.8319	0.087*
C241	0.5158 (7)	0.4632 (8)	0.58597 (18)	0.0523 (14)
H24A	0.5556	0.4133	0.6130	0.078*
H24B	0.5295	0.6008	0.5860	0.078*
H24C	0.5990	0.4091	0.5643	0.078*
C251	0.4216 (10)	0.0690 (8)	0.6025 (2)	0.0612 (16)
H25A	0.5398	0.0658	0.5854	0.092*
H25B	0.3779	−0.0603	0.6081	0.092*
H25C	0.4506	0.1325	0.6288	0.092*

	U11	U22	U33	U12	U13	U23
O11	0.0296 (16)	0.068 (2)	0.0497 (16)	0.0131 (19)	−0.0007 (16)	−0.0057 (19)
O12	0.0329 (16)	0.067 (2)	0.0324 (11)	−0.0016 (19)	−0.0084 (14)	0.0003 (16)
O13	0.069 (3)	0.045 (2)	0.067 (2)	−0.020 (2)	−0.003 (2)	0.0090 (18)
C11	0.026 (2)	0.040 (3)	0.0300 (17)	−0.0028 (19)	0.0027 (16)	−0.0067 (17)
C12	0.046 (3)	0.039 (3)	0.0263 (16)	0.014 (3)	−0.0010 (19)	−0.0137 (17)
C13	0.054 (3)	0.0261 (19)	0.0330 (18)	0.006 (2)	0.001 (2)	0.0034 (15)
C16	0.037 (2)	0.038 (3)	0.0281 (18)	0.006 (2)	0.0088 (19)	−0.0104 (17)
C17	0.043 (3)	0.037 (2)	0.0315 (18)	0.009 (2)	0.0012 (19)	0.0118 (18)
C14	0.039 (3)	0.038 (3)	0.0361 (19)	−0.001 (3)	0.003 (2)	0.0045 (18)
C15	0.043 (3)	0.043 (2)	0.0235 (16)	−0.004 (2)	0.0041 (18)	−0.0050 (16)
C18A	0.077 (5)	0.103 (4)	0.0249 (19)	0.025 (4)	−0.011 (2)	−0.004 (2)
C19A	0.049 (3)	0.056 (3)	0.026 (2)	0.000 (4)	−0.003 (2)	0.003 (3)
C20A	0.069 (4)	0.066 (4)	0.034 (2)	0.002 (3)	0.001 (3)	0.000 (2)
C18B	0.077 (5)	0.103 (4)	0.0249 (19)	0.025 (4)	−0.011 (2)	−0.004 (2)
C19B	0.049 (3)	0.056 (3)	0.026 (2)	0.000 (4)	−0.003 (2)	0.003 (3)
C20B	0.069 (4)	0.066 (4)	0.034 (2)	0.002 (3)	0.001 (3)	0.000 (2)
C111	0.029 (2)	0.034 (2)	0.042 (2)	0.0037 (19)	−0.0016 (18)	−0.007 (2)
C112	0.034 (3)	0.083 (4)	0.0409 (18)	0.019 (3)	0.008 (2)	−0.006 (2)
C113	0.034 (2)	0.035 (2)	0.0333 (17)	−0.002 (2)	0.0013 (19)	−0.0075 (19)
C114	0.043 (3)	0.040 (2)	0.053 (2)	−0.012 (2)	−0.014 (2)	0.003 (2)
C141	0.061 (4)	0.060 (4)	0.047 (2)	0.026 (3)	−0.003 (3)	0.002 (3)
C151	0.052 (3)	0.052 (3)	0.057 (3)	−0.004 (3)	−0.004 (3)	0.008 (2)
O21	0.0226 (14)	0.067 (2)	0.0464 (15)	0.0066 (18)	0.0044 (14)	0.0054 (18)
O22	0.0311 (15)	0.061 (2)	0.0383 (12)	0.0060 (18)	0.0117 (14)	0.0011 (16)
O23	0.096 (3)	0.0341 (18)	0.083 (2)	0.030 (2)	0.035 (3)	0.0178 (18)
C21	0.0238 (19)	0.031 (2)	0.046 (2)	−0.0050 (18)	0.0084 (18)	−0.0005 (17)
C22	0.038 (3)	0.027 (2)	0.065 (3)	−0.003 (2)	0.015 (2)	−0.006 (2)
C23	0.030 (2)	0.0210 (18)	0.059 (2)	−0.0053 (18)	0.014 (2)	−0.0034 (16)
C26	0.039 (3)	0.024 (2)	0.064 (3)	−0.009 (2)	0.008 (2)	−0.0007 (19)
C27	0.038 (3)	0.031 (2)	0.057 (2)	−0.013 (2)	0.014 (2)	−0.016 (2)
C24	0.036 (2)	0.028 (2)	0.038 (2)	0.002 (2)	0.012 (2)	0.0003 (16)
C25	0.039 (3)	0.0191 (18)	0.051 (2)	0.0026 (19)	0.012 (2)	−0.0040 (16)
C28A	0.067 (4)	0.033 (2)	0.064 (3)	0.000 (2)	0.005 (3)	−0.025 (2)
C29A	0.106 (5)	0.084 (5)	0.043 (3)	0.007 (5)	0.002 (3)	−0.004 (3)
C30A	0.073 (4)	0.044 (3)	0.052 (2)	0.017 (3)	0.006 (3)	0.018 (2)
C28B	0.067 (4)	0.033 (2)	0.064 (3)	0.000 (2)	0.005 (3)	−0.025 (2)
C29B	0.106 (5)	0.084 (5)	0.043 (3)	0.007 (5)	0.002 (3)	−0.004 (3)
C30B	0.073 (4)	0.044 (3)	0.052 (2)	0.017 (3)	0.006 (3)	0.018 (2)
C211	0.026 (2)	0.037 (2)	0.0346 (19)	0.002 (2)	0.0069 (18)	−0.007 (2)
C212	0.026 (2)	0.069 (3)	0.0380 (17)	0.017 (2)	0.0119 (19)	0.000 (2)
C213	0.024 (2)	0.029 (2)	0.047 (2)	0.0027 (19)	0.0126 (19)	0.0012 (19)
C214	0.036 (3)	0.091 (4)	0.048 (2)	0.000 (3)	0.027 (2)	−0.002 (3)
C241	0.034 (3)	0.045 (3)	0.078 (3)	−0.005 (2)	0.018 (3)	0.000 (3)
C251	0.048 (3)	0.032 (3)	0.104 (4)	0.025 (2)	0.006 (3)	−0.009 (2)

O11—C113	1.229 (6)	O21—C213	1.193 (6)
O12—C113	1.341 (4)	O22—C213	1.344 (4)
O12—C114	1.413 (6)	O22—C214	1.464 (6)
O13—C13	1.231 (7)	O23—C23	1.206 (7)
C11—C111	1.502 (5)	C21—C211	1.507 (5)
C11—C17	1.513 (6)	C21—C22	1.540 (6)
C11—C12	1.524 (6)	C21—C27	1.560 (6)
C11—H11	0.9800	C21—H21	0.9800
C12—C13	1.571 (5)	C22—C23	1.428 (6)
C12—H12A	0.9700	C22—H22A	0.9700
C12—H12B	0.9700	C22—H22B	0.9700
C13—C14	1.475 (7)	C23—C24	1.554 (6)
C16—C15	1.535 (7)	C26—C27	1.477 (6)
C16—C17	1.554 (5)	C26—C25	1.567 (7)
C16—H16A	0.9700	C26—H26A	0.9700
C16—H16B	0.9700	C26—H26B	0.9700
C17—H17A	0.9700	C27—H27A	0.9700
C17—H17B	0.9700	C27—H27B	0.9700
C14—C141	1.528 (8)	C24—C30A	1.524 (7)
C14—C20A	1.548 (6)	C24—C241	1.567 (8)
C14—C15	1.588 (6)	C24—C25	1.600 (6)
C15—C151	1.498 (8)	C25—C28A	1.502 (6)
C15—C18A	1.582 (5)	C25—C251	1.563 (8)
C18A—C19A	1.501 (10)	C28A—C29A	1.484 (9)
C18A—H18A	0.9700	C28A—H28A	0.9700
C18A—H18B	0.9700	C28A—H28B	0.9700
C19A—C20A	1.509 (10)	C29A—C30A	1.477 (9)
C19A—H19A	0.9700	C29A—H29A	0.9700
C19A—H19B	0.9700	C29A—H29B	0.9700
C20A—H20A	0.9700	C30A—H30A	0.9700
C20A—H20B	0.9700	C30A—H30B	0.9700
C19B—H19C	0.9700	C29B—H29C	0.9700
C19B—H19D	0.9700	C29B—H29D	0.9700
C111—C112	1.339 (7)	C211—C212	1.299 (7)
C111—C113	1.454 (7)	C211—C213	1.508 (6)
C112—H11A	0.9300	C212—H21A	0.9300
C112—H11B	0.9300	C212—H21B	0.9300
C114—H11C	0.9600	C214—H21C	0.9600
C114—H11D	0.9600	C214—H21D	0.9600
C114—H11E	0.9600	C214—H21E	0.9600
C141—H14A	0.9600	C241—H24A	0.9600
C141—H14B	0.9600	C241—H24B	0.9600
C141—H14C	0.9600	C241—H24C	0.9600
C151—H15A	0.9600	C251—H25A	0.9600
C151—H15B	0.9600	C251—H25B	0.9600
C151—H15C	0.9600	C251—H25C	0.9600
C113—O12—C114	118.6 (4)	C213—O22—C214	114.3 (4)
C111—C11—C17	108.3 (4)	C211—C21—C22	112.6 (4)
C111—C11—C12	111.2 (3)	C211—C21—C27	111.9 (4)
C17—C11—C12	114.0 (4)	C22—C21—C27	109.1 (3)
C111—C11—H11	107.7	C211—C21—H21	107.7
C17—C11—H11	107.7	C22—C21—H21	107.7
C12—C11—H11	107.7	C27—C21—H21	107.7
C11—C12—C13	107.6 (4)	C23—C22—C21	113.0 (4)
C11—C12—H12A	110.2	C23—C22—H22A	109.0
C13—C12—H12A	110.2	C21—C22—H22A	109.0
C11—C12—H12B	110.2	C23—C22—H22B	109.0
C13—C12—H12B	110.2	C21—C22—H22B	109.0
H12A—C12—H12B	108.5	H22A—C22—H22B	107.8
O13—C13—C14	124.8 (4)	O23—C23—C22	120.0 (4)
O13—C13—C12	117.5 (5)	O23—C23—C24	118.6 (4)
C14—C13—C12	117.7 (4)	C22—C23—C24	121.2 (4)
C15—C16—C17	118.3 (4)	C27—C26—C25	120.2 (4)
C15—C16—H16A	107.7	C27—C26—H26A	107.3
C17—C16—H16A	107.7	C25—C26—H26A	107.3
C15—C16—H16B	107.7	C27—C26—H26B	107.3
C17—C16—H16B	107.7	C25—C26—H26B	107.3
H16A—C16—H16B	107.1	H26A—C26—H26B	106.9
C11—C17—C16	114.6 (4)	C26—C27—C21	119.0 (4)
C11—C17—H17A	108.6	C26—C27—H27A	107.6
C16—C17—H17A	108.6	C21—C27—H27A	107.6
C11—C17—H17B	108.6	C26—C27—H27B	107.6
C16—C17—H17B	108.6	C21—C27—H27B	107.6
H17A—C17—H17B	107.6	H27A—C27—H27B	107.0
C13—C14—C141	110.1 (4)	C30A—C24—C23	114.0 (4)
C13—C14—C20A	109.0 (4)	C30A—C24—C241	111.5 (4)
C141—C14—C20A	107.5 (5)	C23—C24—C241	104.3 (4)
C13—C14—C15	110.5 (4)	C30A—C24—C25	103.1 (4)
C141—C14—C15	113.6 (5)	C23—C24—C25	111.2 (4)
C20A—C14—C15	106.0 (4)	C241—C24—C25	113.0 (4)
C151—C15—C16	111.9 (4)	C28A—C25—C251	111.4 (4)
C151—C15—C18A	108.5 (5)	C28A—C25—C26	109.8 (4)
C16—C15—C18A	105.1 (4)	C251—C25—C26	107.4 (4)
C151—C15—C14	115.8 (5)	C28A—C25—C24	103.4 (4)
C16—C15—C14	112.8 (4)	C251—C25—C24	112.8 (5)
C18A—C15—C14	101.6 (4)	C26—C25—C24	112.2 (4)
C19A—C18A—C15	109.9 (5)	C29A—C28A—C25	110.6 (4)
C19A—C18A—H18A	109.7	C29A—C28A—H28A	109.5
C15—C18A—H18A	109.7	C25—C28A—H28A	109.5
C19A—C18A—H18B	109.7	C29A—C28A—H28B	109.5
C15—C18A—H18B	109.7	C25—C28A—H28B	109.5
H18A—C18A—H18B	108.2	H28A—C28A—H28B	108.1
C18A—C19A—C20A	103.9 (5)	C30A—C29A—C28A	104.6 (4)
C18A—C19A—H19A	111.0	C30A—C29A—H29A	110.8
C20A—C19A—H19A	111.0	C28A—C29A—H29A	110.8
C18A—C19A—H19B	111.0	C30A—C29A—H29B	110.8
C20A—C19A—H19B	111.0	C28A—C29A—H29B	110.8
H19A—C19A—H19B	109.0	H29A—C29A—H29B	108.9
C19A—C20A—C14	104.8 (5)	C29A—C30A—C24	106.2 (5)
C19A—C20A—H20A	110.8	C29A—C30A—H30A	110.5
C14—C20A—H20A	110.8	C24—C30A—H30A	110.5
C19A—C20A—H20B	110.8	C29A—C30A—H30B	110.5
C14—C20A—H20B	110.8	C24—C30A—H30B	110.5
H20A—C20A—H20B	108.9	H30A—C30A—H30B	108.7
H19C—C19B—H19D	108.2	H29C—C29B—H29D	108.8
C112—C111—C113	119.3 (4)	C212—C211—C21	125.1 (4)
C112—C111—C11	123.4 (4)	C212—C211—C213	119.6 (3)
C113—C111—C11	117.3 (4)	C21—C211—C213	115.2 (4)
C111—C112—H11A	120.0	C211—C212—H21A	120.0
C111—C112—H11B	120.0	C211—C212—H21B	120.0
H11A—C112—H11B	120.0	H21A—C212—H21B	120.0
O11—C113—O12	121.3 (4)	O21—C213—O22	124.9 (4)
O11—C113—C111	124.7 (3)	O21—C213—C211	123.5 (3)
O12—C113—C111	113.9 (4)	O22—C213—C211	111.6 (4)
O12—C114—H11C	109.5	O22—C214—H21C	109.5
O12—C114—H11D	109.5	O22—C214—H21D	109.5
H11C—C114—H11D	109.5	H21C—C214—H21D	109.5
O12—C114—H11E	109.5	O22—C214—H21E	109.5
H11C—C114—H11E	109.5	H21C—C214—H21E	109.5
H11D—C114—H11E	109.5	H21D—C214—H21E	109.5
C14—C141—H14A	109.5	C24—C241—H24A	109.5
C14—C141—H14B	109.5	C24—C241—H24B	109.5
H14A—C141—H14B	109.5	H24A—C241—H24B	109.5
C14—C141—H14C	109.5	C24—C241—H24C	109.5
H14A—C141—H14C	109.5	H24A—C241—H24C	109.5
H14B—C141—H14C	109.5	H24B—C241—H24C	109.5
C15—C151—H15A	109.5	C25—C251—H25A	109.5
C15—C151—H15B	109.5	C25—C251—H25B	109.5
H15A—C151—H15B	109.5	H25A—C251—H25B	109.5
C15—C151—H15C	109.5	C25—C251—H25C	109.5
H15A—C151—H15C	109.5	H25A—C251—H25C	109.5
H15B—C151—H15C	109.5	H25B—C251—H25C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C112—H11B···O11i	0.93	2.42	3.325 (7)	165
C212—H21A···O21i	0.93	2.45	3.348 (6)	162
C26—H26B···O23ii	0.97	2.58	3.427 (6)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C112—H11B⋯O11i	0.93	2.42	3.325 (7)	165
C212—H21A⋯O21i	0.93	2.45	3.348 (6)	162
C26—H26B⋯O23ii	0.97	2.58	3.427 (6)	146

Symmetry codes: (i) ; (ii) .