Methyl 5a-acetoxy-methyl-3-isopropyl-8-methyl-1,2,3,3a,4,5,5a,6,7,10,10a,10b-dodeca-hydro-7,10-endo-epidioxy-cylohepta-[e]indene-3a-carboxyl-ate.

The mol-ecule of the title compound, C(23)H(34)O(6), is built up from three fused carbocycles, one five-membered, one six-membered and one seven-membered. The five-membered ring has an envelope conformation, whereas the six-membered ring has a perfect chair conformation and the seven-membered ring has a boat conformation. Intra-molecular C-H⋯O hydrogen bonds together with van der Waals inter-actions stabilize the mol-ecular conformation.

Related literature

For related literature, see: Araya et al. (2003 ▶); Cremer & Pople (1975 ▶); Loyola et al. (1990 ▶, 2004 ▶); Munizaga & Gunkel (1958 ▶).

Experimental

Crystal data

C23H34O6

M = 406.5

Orthorhombic,

a = 7.7014 (1) Å

b = 12.1234 (3) Å

c = 23.2773 (6) Å

V = 2173.34 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 (2) K

0.24 × 0.24 × 0.02 mm

Data collection

Nonius KappaCCD area-detector diffractometer

Absorption correction: none

5538 measured reflections

3052 independent reflections

2499 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.127

S = 1.08

3052 reflections

269 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.16 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808016474/bt2719sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808016474/bt2719Isup2.hkl

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

C23H34O6	F000 = 880
Mr = 406.5	Dx = 1.242 Mg m−3
Orthorhombic, P212121	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4314 reflections
a = 7.70140 (10) Å	θ = 6.5–28.5º
b = 12.1234 (3) Å	µ = 0.09 mm−1
c = 23.2773 (6) Å	T = 298 (2) K
V = 2173.34 (8) Å3	Block, colourless
Z = 4	0.24 × 0.24 × 0.02 mm

Nonius KappaCCD area-detector diffractometer	2499 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.031
Monochromator: graphite	θmax = 28.7º
φ scans, and ω scans with κ offsets	θmin = 6.5º
Absorption correction: none	h = 0→9
5538 measured reflections	k = 0→16
3052 independent reflections	l = −31→31

Refinement on F2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.0421P)2 + 0.8253P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.059	(Δ/σ)max = 0.007
wR(F2) = 0.127	Δρmax = 0.22 e Å−3
S = 1.08	Δρmin = −0.16 e Å−3
3052 reflections	Extinction correction: none
269 parameters

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	−0.2384 (3)	0.1347 (2)	0.68889 (10)	0.0639 (7)
O2	−0.1528 (4)	0.2323 (2)	0.71350 (11)	0.0687 (7)
O3	0.3065 (3)	−0.10383 (17)	0.68850 (9)	0.0518 (5)
O4	0.5474 (3)	−0.1354 (2)	0.73855 (15)	0.0867 (9)
O5	0.0901 (3)	−0.14722 (16)	0.55258 (10)	0.0552 (6)
O6	0.3186 (3)	−0.06177 (16)	0.51523 (9)	0.0487 (5)
C1	−0.2121 (4)	0.0030 (3)	0.57004 (13)	0.0535 (8)
H1A	−0.3169	0.039	0.5835	0.052 (2)*
H1B	−0.2162	−0.0742	0.5808	0.052 (2)*
C2	−0.1933 (4)	0.0156 (3)	0.50447 (14)	0.0591 (8)
H2A	−0.2915	0.0558	0.4889	0.052 (2)*
H2B	−0.1885	−0.0563	0.4863	0.052 (2)*
C3	−0.0234 (4)	0.0795 (2)	0.49338 (12)	0.0473 (7)
H3	−0.0524	0.1582	0.4954	0.052 (2)*
C3A	0.0889 (3)	0.0529 (2)	0.54768 (11)	0.0343 (5)
C4	0.2315 (4)	0.1336 (2)	0.56491 (12)	0.0398 (6)
H4A	0.3203	0.136	0.5354	0.052 (2)*
H4B	0.1834	0.2071	0.5692	0.052 (2)*
C5	0.3105 (4)	0.0957 (2)	0.62158 (12)	0.0415 (6)
H5A	0.3964	0.1499	0.6331	0.052 (2)*
H5B	0.3717	0.0271	0.6146	0.052 (2)*
C5A	0.1856 (3)	0.0774 (2)	0.67296 (11)	0.0347 (5)
C6	0.1561 (4)	0.1917 (2)	0.70137 (13)	0.0468 (7)
H6A	0.2622	0.2115	0.7213	0.052 (2)*
H6B	0.1402	0.2451	0.6708	0.052 (2)*
C7	0.0054 (5)	0.2063 (3)	0.74379 (14)	0.0525 (8)
H7	0.0334	0.2706	0.7676	0.052 (2)*
C8	−0.0245 (4)	0.1123 (3)	0.78396 (13)	0.0508 (8)
C9	−0.0977 (4)	0.0257 (3)	0.75995 (13)	0.0520 (8)
H9	−0.1209	−0.038	0.7808	0.052 (2)*
C10	−0.1419 (4)	0.0345 (3)	0.69763 (13)	0.0470 (7)
H10	−0.2224	−0.0261	0.6894	0.052 (2)*
C10A	0.0111 (3)	0.0217 (2)	0.65466 (11)	0.0337 (5)
H10A	0.0347	−0.0575	0.6517	0.052 (2)*
C10B	−0.0497 (3)	0.0591 (2)	0.59511 (11)	0.0356 (6)
H10B	−0.0792	0.1373	0.599	0.052 (2)*
C11	0.0302 (6)	0.1227 (4)	0.84575 (14)	0.0737 (11)
H11A	−0.0064	0.0584	0.8666	0.105 (4)*
H11B	−0.0224	0.1871	0.8623	0.105 (4)*
H11C	0.1543	0.1292	0.8478	0.105 (4)*
C12	0.2888 (4)	0.0041 (3)	0.71470 (13)	0.0462 (7)
H12A	0.4025	0.0358	0.7218	0.052 (2)*
H12B	0.228	−0.0019	0.7511	0.052 (2)*
C13	0.4416 (4)	−0.1652 (3)	0.70431 (15)	0.0500 (8)
C14	0.4426 (5)	−0.2734 (3)	0.67401 (19)	0.0705 (10)
H14A	0.5582	−0.2896	0.6611	0.105 (4)*
H14B	0.3658	−0.2702	0.6416	0.105 (4)*
H14C	0.4046	−0.3302	0.6998	0.105 (4)*
C15	0.1611 (3)	−0.0632 (2)	0.53996 (11)	0.0355 (5)
C16	0.3949 (5)	−0.1677 (3)	0.50295 (16)	0.0618 (9)
H16A	0.4036	−0.2097	0.5378	0.105 (4)*
H16B	0.5087	−0.1574	0.4869	0.105 (4)*
H16C	0.3234	−0.2066	0.4759	0.105 (4)*
C17	0.0546 (5)	0.0591 (3)	0.43302 (13)	0.0569 (8)
H17	0.0958	−0.0174	0.4319	0.052 (2)*
C18	0.2077 (7)	0.1326 (4)	0.41986 (16)	0.0870 (14)
H18A	0.1763	0.2081	0.4267	0.105 (4)*
H18B	0.2407	0.1236	0.3804	0.105 (4)*
H18C	0.3034	0.1129	0.4442	0.105 (4)*
C19	−0.0846 (7)	0.0713 (4)	0.38666 (15)	0.0855 (14)
H19A	−0.1338	0.144	0.3886	0.105 (4)*
H19B	−0.1741	0.0175	0.3928	0.105 (4)*
H19C	−0.0333	0.0602	0.3495	0.105 (4)*

	U11	U22	U33	U12	U13	U23
O1	0.0484 (12)	0.0844 (17)	0.0589 (13)	0.0207 (13)	0.0003 (11)	−0.0204 (13)
O2	0.0731 (16)	0.0593 (15)	0.0738 (16)	0.0192 (14)	0.0024 (14)	0.0054 (13)
O3	0.0489 (12)	0.0487 (11)	0.0579 (12)	0.0085 (10)	−0.0136 (11)	−0.0031 (10)
O4	0.0587 (16)	0.0741 (18)	0.127 (2)	0.0043 (14)	−0.0425 (18)	0.0106 (17)
O5	0.0608 (13)	0.0319 (10)	0.0730 (15)	−0.0098 (10)	0.0136 (12)	−0.0067 (10)
O6	0.0469 (11)	0.0377 (10)	0.0617 (12)	0.0068 (10)	0.0138 (10)	−0.0047 (10)
C1	0.0323 (15)	0.074 (2)	0.0541 (17)	−0.0029 (15)	−0.0033 (13)	−0.0075 (16)
C2	0.0488 (17)	0.076 (2)	0.0520 (17)	0.0034 (17)	−0.0165 (15)	−0.0075 (17)
C3	0.0612 (18)	0.0406 (15)	0.0401 (14)	0.0098 (14)	−0.0074 (14)	−0.0016 (12)
C3A	0.0391 (13)	0.0287 (12)	0.0351 (12)	0.0006 (11)	0.0014 (11)	−0.0003 (10)
C4	0.0450 (15)	0.0311 (13)	0.0435 (14)	−0.0062 (12)	0.0101 (12)	−0.0040 (11)
C5	0.0326 (13)	0.0429 (15)	0.0490 (15)	−0.0102 (12)	0.0035 (12)	−0.0077 (12)
C5A	0.0335 (12)	0.0346 (13)	0.0360 (12)	−0.0055 (11)	−0.0015 (11)	−0.0061 (11)
C6	0.0563 (18)	0.0379 (15)	0.0461 (16)	−0.0087 (14)	0.0008 (14)	−0.0086 (13)
C7	0.070 (2)	0.0420 (16)	0.0460 (16)	−0.0030 (17)	0.0046 (16)	−0.0103 (13)
C8	0.0541 (17)	0.0584 (19)	0.0400 (15)	0.0037 (16)	0.0076 (14)	−0.0049 (14)
C9	0.0612 (19)	0.0476 (16)	0.0471 (16)	−0.0007 (16)	0.0176 (15)	0.0010 (13)
C10	0.0398 (14)	0.0531 (17)	0.0482 (16)	−0.0100 (13)	0.0097 (13)	−0.0049 (14)
C10A	0.0288 (11)	0.0343 (12)	0.0379 (13)	−0.0026 (11)	0.0014 (10)	−0.0047 (10)
C10B	0.0298 (12)	0.0363 (13)	0.0408 (13)	0.0032 (11)	0.0004 (10)	−0.0040 (11)
C11	0.080 (3)	0.097 (3)	0.0439 (18)	0.003 (2)	−0.0008 (19)	−0.0052 (19)
C12	0.0418 (15)	0.0522 (17)	0.0447 (15)	0.0055 (14)	−0.0078 (13)	−0.0073 (13)
C13	0.0363 (15)	0.0521 (18)	0.0615 (19)	0.0016 (13)	0.0014 (14)	0.0189 (15)
C14	0.067 (2)	0.054 (2)	0.090 (3)	0.0167 (19)	0.006 (2)	0.0085 (19)
C15	0.0399 (13)	0.0326 (12)	0.0342 (12)	−0.0005 (12)	−0.0027 (11)	−0.0035 (11)
C16	0.067 (2)	0.0506 (18)	0.068 (2)	0.0200 (17)	0.0143 (19)	−0.0075 (16)
C17	0.084 (2)	0.0468 (16)	0.0399 (15)	0.0123 (19)	−0.0024 (16)	0.0003 (14)
C18	0.123 (4)	0.088 (3)	0.0499 (19)	−0.016 (3)	0.020 (2)	0.005 (2)
C19	0.128 (4)	0.083 (3)	0.0457 (18)	0.032 (3)	−0.021 (2)	−0.0038 (19)

O1—C10	1.438 (4)	C6—H6B	0.97
O1—O2	1.470 (4)	C7—C8	1.492 (5)
O2—C7	1.443 (5)	C7—H7	0.98
O3—C13	1.331 (4)	C8—C9	1.316 (5)
O3—C12	1.450 (4)	C8—C11	1.504 (5)
O4—C13	1.196 (4)	C9—C10	1.494 (5)
O5—C15	1.193 (3)	C9—H9	0.93
O6—C15	1.342 (3)	C10—C10A	1.554 (4)
O6—C16	1.441 (4)	C10—H10	0.98
C1—C10B	1.538 (4)	C10A—C10B	1.532 (4)
C1—C2	1.541 (5)	C10A—H10A	0.98
C1—H1A	0.97	C10B—H10B	0.98
C1—H1B	0.97	C11—H11A	0.96
C2—C3	1.542 (5)	C11—H11B	0.96
C2—H2A	0.97	C11—H11C	0.96
C2—H2B	0.97	C12—H12A	0.97
C3—C17	1.548 (4)	C12—H12B	0.97
C3—C3A	1.565 (4)	C13—C14	1.490 (5)
C3—H3	0.98	C14—H14A	0.96
C3A—C4	1.524 (4)	C14—H14B	0.96
C3A—C15	1.525 (4)	C14—H14C	0.96
C3A—C10B	1.538 (4)	C16—H16A	0.96
C4—C5	1.523 (4)	C16—H16B	0.96
C4—H4A	0.97	C16—H16C	0.96
C4—H4B	0.97	C17—C18	1.510 (6)
C5—C5A	1.551 (4)	C17—C19	1.528 (5)
C5—H5A	0.97	C17—H17	0.98
C5—H5B	0.97	C18—H18A	0.96
C5A—C12	1.538 (4)	C18—H18B	0.96
C5A—C6	1.553 (4)	C18—H18C	0.96
C5A—C10A	1.563 (3)	C19—H19A	0.96
C6—C7	1.534 (5)	C19—H19B	0.96
C6—H6A	0.97	C19—H19C	0.96
C10—O1—O2	113.1 (2)	O1—C10—C10A	112.7 (2)
C7—O2—O1	113.1 (2)	C9—C10—C10A	116.4 (2)
C13—O3—C12	117.5 (2)	O1—C10—H10	106.2
C15—O6—C16	116.2 (2)	C9—C10—H10	106.2
C10B—C1—C2	104.8 (3)	C10A—C10—H10	106.2
C10B—C1—H1A	110.8	C10B—C10A—C10	108.7 (2)
C2—C1—H1A	110.8	C10B—C10A—C5A	112.5 (2)
C10B—C1—H1B	110.8	C10—C10A—C5A	115.7 (2)
C2—C1—H1B	110.8	C10B—C10A—H10A	106.5
H1A—C1—H1B	108.9	C10—C10A—H10A	106.5
C1—C2—C3	107.2 (2)	C5A—C10A—H10A	106.5
C1—C2—H2A	110.3	C10A—C10B—C3A	115.0 (2)
C3—C2—H2A	110.3	C10A—C10B—C1	117.5 (2)
C1—C2—H2B	110.3	C3A—C10B—C1	105.7 (2)
C3—C2—H2B	110.3	C10A—C10B—H10B	105.9
H2A—C2—H2B	108.5	C3A—C10B—H10B	105.9
C2—C3—C17	113.6 (3)	C1—C10B—H10B	105.9
C2—C3—C3A	103.3 (2)	C8—C11—H11A	109.5
C17—C3—C3A	119.0 (3)	C8—C11—H11B	109.5
C2—C3—H3	106.7	H11A—C11—H11B	109.5
C17—C3—H3	106.7	C8—C11—H11C	109.5
C3A—C3—H3	106.7	H11A—C11—H11C	109.5
C4—C3A—C15	111.2 (2)	H11B—C11—H11C	109.5
C4—C3A—C10B	106.3 (2)	O3—C12—C5A	107.7 (2)
C15—C3A—C10B	112.5 (2)	O3—C12—H12A	110.2
C4—C3A—C3	118.6 (2)	C5A—C12—H12A	110.2
C15—C3A—C3	107.3 (2)	O3—C12—H12B	110.2
C10B—C3A—C3	100.7 (2)	C5A—C12—H12B	110.2
C5—C4—C3A	108.8 (2)	H12A—C12—H12B	108.5
C5—C4—H4A	109.9	O4—C13—O3	123.3 (3)
C3A—C4—H4A	109.9	O4—C13—C14	125.3 (3)
C5—C4—H4B	109.9	O3—C13—C14	111.4 (3)
C3A—C4—H4B	109.9	C13—C14—H14A	109.5
H4A—C4—H4B	108.3	C13—C14—H14B	109.5
C4—C5—C5A	117.6 (2)	H14A—C14—H14B	109.5
C4—C5—H5A	107.9	C13—C14—H14C	109.5
C5A—C5—H5A	107.9	H14A—C14—H14C	109.5
C4—C5—H5B	107.9	H14B—C14—H14C	109.5
C5A—C5—H5B	107.9	O5—C15—O6	122.1 (3)
H5A—C5—H5B	107.2	O5—C15—C3A	126.3 (2)
C12—C5A—C5	104.5 (2)	O6—C15—C3A	111.6 (2)
C12—C5A—C6	108.8 (2)	O6—C16—H16A	109.5
C5—C5A—C6	106.9 (2)	O6—C16—H16B	109.5
C12—C5A—C10A	111.5 (2)	H16A—C16—H16B	109.5
C5—C5A—C10A	112.6 (2)	O6—C16—H16C	109.5
C6—C5A—C10A	112.1 (2)	H16A—C16—H16C	109.5
C7—C6—C5A	119.2 (2)	H16B—C16—H16C	109.5
C7—C6—H6A	107.5	C18—C17—C19	110.3 (3)
C5A—C6—H6A	107.5	C18—C17—C3	113.1 (3)
C7—C6—H6B	107.5	C19—C17—C3	110.7 (3)
C5A—C6—H6B	107.5	C18—C17—H17	107.5
H6A—C6—H6B	107	C19—C17—H17	107.5
O2—C7—C8	110.1 (3)	C3—C17—H17	107.5
O2—C7—C6	110.4 (2)	C17—C18—H18A	109.5
C8—C7—C6	115.6 (3)	C17—C18—H18B	109.5
O2—C7—H7	106.7	H18A—C18—H18B	109.5
C8—C7—H7	106.7	C17—C18—H18C	109.5
C6—C7—H7	106.7	H18A—C18—H18C	109.5
C9—C8—C7	114.1 (3)	H18B—C18—H18C	109.5
C9—C8—C11	126.4 (3)	C17—C19—H19A	109.5
C7—C8—C11	119.5 (3)	C17—C19—H19B	109.5
C8—C9—C10	117.0 (3)	H19A—C19—H19B	109.5
C8—C9—H9	121.5	C17—C19—H19C	109.5
C10—C9—H9	121.5	H19A—C19—H19C	109.5
O1—C10—C9	108.4 (2)	H19B—C19—H19C	109.5
C10—O1—O2—C7	−3.0 (3)	C9—C10—C10A—C5A	−39.5 (4)
C10B—C1—C2—C3	−0.8 (4)	C12—C5A—C10A—C10B	−152.2 (2)
C1—C2—C3—C17	156.3 (3)	C5—C5A—C10A—C10B	−35.1 (3)
C1—C2—C3—C3A	25.9 (3)	C6—C5A—C10A—C10B	85.5 (3)
C2—C3—C3A—C4	−155.8 (2)	C12—C5A—C10A—C10	82.1 (3)
C17—C3—C3A—C4	77.2 (3)	C5—C5A—C10A—C10	−160.9 (2)
C2—C3—C3A—C15	77.4 (3)	C6—C5A—C10A—C10	−40.2 (3)
C17—C3—C3A—C15	−49.7 (3)	C10—C10A—C10B—C3A	179.1 (2)
C2—C3—C3A—C10B	−40.4 (3)	C5A—C10A—C10B—C3A	49.7 (3)
C17—C3—C3A—C10B	−167.5 (3)	C10—C10A—C10B—C1	−55.4 (3)
C15—C3A—C4—C5	−60.2 (3)	C5A—C10A—C10B—C1	175.1 (2)
C10B—C3A—C4—C5	62.4 (3)	C4—C3A—C10B—C10A	−63.6 (3)
C3—C3A—C4—C5	174.8 (2)	C15—C3A—C10B—C10A	58.3 (3)
C3A—C4—C5—C5A	−54.7 (3)	C3—C3A—C10B—C10A	172.2 (2)
C4—C5—C5A—C12	161.1 (2)	C4—C3A—C10B—C1	165.1 (2)
C4—C5—C5A—C6	−83.6 (3)	C15—C3A—C10B—C1	−73.0 (3)
C4—C5—C5A—C10A	39.9 (3)	C3—C3A—C10B—C1	40.9 (3)
C12—C5A—C6—C7	−82.6 (3)	C2—C1—C10B—C10A	−155.3 (3)
C5—C5A—C6—C7	165.1 (3)	C2—C1—C10B—C3A	−25.3 (3)
C10A—C5A—C6—C7	41.2 (4)	C13—O3—C12—C5A	154.3 (2)
O1—O2—C7—C8	−48.3 (3)	C5—C5A—C12—O3	−69.1 (3)
O1—O2—C7—C6	80.6 (3)	C6—C5A—C12—O3	177.0 (2)
C5A—C6—C7—O2	−85.8 (3)	C10A—C5A—C12—O3	52.8 (3)
C5A—C6—C7—C8	40.0 (4)	C12—O3—C13—O4	−0.2 (5)
O2—C7—C8—C9	51.4 (4)	C12—O3—C13—C14	179.9 (3)
C6—C7—C8—C9	−74.6 (4)	C16—O6—C15—O5	2.0 (4)
O2—C7—C8—C11	−129.2 (3)	C16—O6—C15—C3A	−176.7 (3)
C6—C7—C8—C11	104.8 (4)	C4—C3A—C15—O5	143.0 (3)
C7—C8—C9—C10	−1.0 (4)	C10B—C3A—C15—O5	23.9 (4)
C11—C8—C9—C10	179.7 (3)	C3—C3A—C15—O5	−85.9 (3)
O2—O1—C10—C9	51.2 (3)	C4—C3A—C15—O6	−38.5 (3)
O2—O1—C10—C10A	−79.1 (3)	C10B—C3A—C15—O6	−157.5 (2)
C8—C9—C10—O1	−50.8 (4)	C3—C3A—C15—O6	92.6 (3)
C8—C9—C10—C10A	77.4 (4)	C2—C3—C17—C18	172.8 (3)
O1—C10—C10A—C10B	−41.0 (3)	C3A—C3—C17—C18	−65.2 (4)
C9—C10—C10A—C10B	−167.1 (3)	C2—C3—C17—C19	48.4 (4)
O1—C10—C10A—C5A	86.6 (3)	C3A—C3—C17—C19	170.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5B···O3	0.97	2.39	2.877 (3)	110
C10A—H10A···O3	0.98	2.33	2.848 (3)	112
C10B—H10B···O1	0.98	2.43	2.778 (3)	101

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5B⋯O3	0.97	2.39	2.877 (3)	110
C10A—H10A⋯O3	0.98	2.33	2.848 (3)	112
C10B—H10B⋯O1	0.98	2.43	2.778 (3)	101