24-Methyl­lanosta-7,25-dien-3-one

Hussain, N.; Habib-ur-Rehman; Parvez, M.

doi:10.1107/S1600536810005118

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page o626

doi:10.1107/S1600536810005118

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24-Methyllanosta-7,25-dien-3-one

Nisar Hussain,^a Habib-ur-Rehman ^a and Masood Parvez ^b ^*

^aDepartment of Chemistry, University of Azad Jammu and Kashmir, Muzaffarabad 13100, Pakistan, and ^bDepartment of Chemistry, University of Calgary, 2500 University Drive NW, Calgary, Alberta, Canada T2N 1N4
^*Correspondence e-mail: parvez@ucalgary.ca

(Received 17 January 2010; accepted 8 February 2010; online 13 February 2010)

The title compound [systematic name: 17-(5,6-dimethylhept-6-en-2-yl)-4,4,10,13,14-pentamethyl-1,5,6,10,11,12,13,15,16,17-decahydro-2H-cyclopenta[α]phenanthren-3(4H,9H,14H)-one], C₃₁H₅₀O, is a triterpenoid which was isolated from Skimmia laureola. The three six-membered rings adopt chair, slightly distorted half-chair and distorted boat conformations, and the five-membered ring is in an envelope conformation. All the rings are trans fused. In the crystal structure, there is a weak C—H⋯O hydrogen bond.

Related literature

For related structures, see: Hussain et al. (2009 ); Schun et al. (1986 ). For reference bond lengths, see: Allen et al. (1987 ). For puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₃₁H₅₀O
M_r = 438.71
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.7207 (1) Å
b = 19.4804 (5) Å
c = 20.5035 (5) Å
V = 2684.36 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.06 mm⁻¹
T = 173 K
0.30 × 0.05 × 0.04 mm

Data collection

Nonius diffractometer with Bruker APEXII CCD
Absorption correction: multi-scan (SORTAV; Blessing, 1997 ) T_min = 0.981, T_max = 0.997
6101 measured reflections
3485 independent reflections
2918 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.122
S = 1.15
3485 reflections
297 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16A⋯O1ⁱ	0.99	2.55	3.528 (4)	169
Symmetry code: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: COLLECT (Nonius, 1998 ); cell refinement: HKL DENZO (Otwinowski & Minor, 1997 ); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810005118/lh2983sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810005118/lh2983Isup2.hkl

checkCIF report

Comment top

The methanol extract of Skimmia laureola affords a novel triterpene, o-methyl cyclolaudenol, the structure of which has been reported recently from our laboratory (Hussain et al. 2009). In this paper, we report the crystal structure of yet an other triterpene which has been isolated from Skimmia laureola, 17-(5,6-dimethylhept-6-en-2-yl)-4,4,10,13,14-pentamethyl- 1,5,6,10,11,12,13,15,16,17-decahydro-2H-cyclopenta[α]phenanthren- 3(4H,9H,14H)-one, (I).

The molecular structure of (I) is presented in Fig. 1. The molecule contains three six-membered rings, A, B and C and a five-membered ring, D. The ring A adopts a chair conformation. The rings B and C show disotortions due to the trans-fused ring D, exhibiting slightly distorted half-chair and distorted boat conformations, respectively. The puckering parameters (Cremer & Pople, 1975) for the rings A to C are: Q = 0.521 (3), 0.563 (3), 0.718 (3) Å, θ = 13.5 (3), 49.0 (3), 94.4 (2)° and ϕ = 27.6 (15), 319.3 (4), 89.9 (2)°, respectively. The ring D adopts a C14-envelope conformation. All rings are trans fused. The crystal structure of a very closely related compound, 24-methylene-25-methyltirucall-7-en-3-one, which is isomorphous with (I), has been reported (Schun et al., 1986). The bond distances (Allen et al., 1987) and angles in (I) are as expected. The structure is devoid of any classical hydrogen bonds. However, a non-classical hydrogen bonding interaction of the type C—H···O is present (Fig. 2 and Table 1).

Related literature top

For related structures, see: Hussain et al. (2009); Schun et al. (1986). For reference bond lengths, see: Allen et al. (1987). For puckering parameters, see: Cremer & Pople (1975).

Experimental top

The methanol extract of Skimmia laureola was subjected to silica-gel column chromatography. The column was eluted with increasing polarities of pet. ether/CHCl₃. This afforded 4 fractions (PC1–PC4). The fraction PC3 (18 g) obtained by elution with 1 litre of pet. ether/CHCl₃ (7.0:3.0) was subjected to the column chromatography. The column was successively eluted with 2 litre of pet. ether and 3 litre of pet. ether/CHCl₃ (ranging from 9.0:1.0 to 7.0:3.0) to afford 7 fractions (PC3A–PC3G). The fraction PC3-G (1.4 g) obtained by elution of the column with 500 ml of pet. ether/CHCl₃ (7.0:3.0) was further subjected to the column chromatography using 500 ml of pet. ether/CHCl₃ (9.8:0.2) to afford the title triterpene, (I), as colourless crystals in needle form.

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: HKL DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. ORTEP-3 (Farrugia, 1997) drawing of (I) with displacement ellipsoids plotted at 50% probability level.
	Fig. 2. Unit cell packing of (I) showing non-classical hydrogen bonding interaction with dashed lines; H atoms not involved in H-bonds have been excluded for clarity.

17-(5,6-Dimethylhept-6-en-2-yl)-4,4,10,13,14-pentamethyl- 1,5,6,10,11,12,13,15,16,17-decahydro-2H-cyclopenta[α]phenanthren- 3(4H,9H,14H)-one top

Crystal data top

C₃₁H₅₀O	F(000) = 976
M_r = 438.71	D_x = 1.086 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3435 reflections
a = 6.7207 (1) Å	θ = 1.0–27.5°
b = 19.4804 (5) Å	µ = 0.06 mm⁻¹
c = 20.5035 (5) Å	T = 173 K
V = 2684.36 (10) Å³	Needle, colourless
Z = 4	0.30 × 0.05 × 0.04 mm

Data collection top

Nonius APEXII CCD diffractometer	3485 independent reflections
Radiation source: fine-focus sealed tube	2918 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ϕ and ω scans	θ_max = 27.5°, θ_min = 2.3°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −8→8
T_min = 0.981, T_max = 0.997	k = −25→25
6101 measured reflections	l = −26→26

Refinement top

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.122	H-atom parameters constrained
S = 1.15	w = 1/[σ²(F_o²) + (0.0302P)² + 1.38P] where P = (F_o² + 2F_c²)/3
3485 reflections	(Δ/σ)_max < 0.001
297 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₃₁H₅₀O	V = 2684.36 (10) Å³
M_r = 438.71	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 6.7207 (1) Å	µ = 0.06 mm⁻¹
b = 19.4804 (5) Å	T = 173 K
c = 20.5035 (5) Å	0.30 × 0.05 × 0.04 mm

Data collection top

Nonius APEXII CCD diffractometer	3485 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	2918 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.997	R_int = 0.036
6101 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.122	H-atom parameters constrained
S = 1.15	Δρ_max = 0.21 e Å⁻³
3485 reflections	Δρ_min = −0.20 e Å⁻³
297 parameters

Special details top

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.

An absolute structure could not be established reliably becuase of insufficient anomalous scattering effects. Therefore, Friedel pairs (2616) were merged.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.8042 (3)	0.08030 (13)	0.84879 (12)	0.0529 (6)
C1	0.5810 (5)	0.11757 (16)	0.70242 (16)	0.0381 (7)
H1A	0.5754	0.0994	0.6574	0.046*
H1B	0.6867	0.1529	0.7039	0.046*
C2	0.6360 (5)	0.05905 (15)	0.74898 (15)	0.0409 (7)
H2A	0.5329	0.0228	0.7472	0.049*
H2B	0.7646	0.0386	0.7357	0.049*
C3	0.6518 (5)	0.08664 (15)	0.81701 (16)	0.0371 (7)
C4	0.4696 (4)	0.12362 (15)	0.84386 (14)	0.0329 (6)
C5	0.3849 (4)	0.17454 (14)	0.79152 (13)	0.0282 (6)
H5	0.4778	0.2146	0.7924	0.034*
C6	0.1812 (5)	0.20449 (15)	0.81055 (14)	0.0351 (7)
H6A	0.0845	0.1665	0.8159	0.042*
H6B	0.1932	0.2284	0.8530	0.042*
C7	0.1042 (4)	0.25387 (14)	0.76047 (13)	0.0308 (6)
H7	−0.0055	0.2821	0.7720	0.037*
C8	0.1798 (4)	0.26067 (13)	0.70088 (13)	0.0251 (6)
C9	0.3595 (4)	0.21892 (13)	0.67906 (12)	0.0264 (6)
H9	0.4789	0.2473	0.6900	0.032*
C10	0.3811 (4)	0.15119 (14)	0.71894 (13)	0.0292 (6)
C11	0.3635 (5)	0.20920 (14)	0.60485 (13)	0.0334 (7)
H11A	0.2515	0.1790	0.5921	0.040*
H11B	0.4886	0.1857	0.5927	0.040*
C12	0.3484 (5)	0.27749 (14)	0.56601 (13)	0.0322 (6)
H12A	0.4841	0.2918	0.5530	0.039*
H12B	0.2717	0.2689	0.5256	0.039*
C13	0.2496 (4)	0.33709 (13)	0.60346 (12)	0.0246 (5)
C14	0.0865 (4)	0.30780 (13)	0.64965 (13)	0.0253 (5)
C15	−0.0160 (4)	0.37378 (14)	0.67363 (13)	0.0291 (6)
H15A	0.0609	0.3955	0.7093	0.035*
H15B	−0.1525	0.3641	0.6893	0.035*
C16	−0.0200 (4)	0.42041 (14)	0.61205 (13)	0.0292 (6)
H16A	0.0215	0.4677	0.6234	0.035*
H16B	−0.1559	0.4222	0.5936	0.035*
C17	0.1276 (4)	0.38854 (13)	0.56168 (12)	0.0256 (6)
H17	0.0464	0.3608	0.5305	0.031*
C18	0.4052 (4)	0.37806 (14)	0.64288 (14)	0.0313 (6)
H18A	0.3456	0.4210	0.6583	0.038*
H18B	0.5197	0.3885	0.6150	0.038*
H18C	0.4491	0.3507	0.6803	0.038*
C19	0.2087 (5)	0.10171 (15)	0.70309 (16)	0.0376 (7)
H19A	0.0817	0.1259	0.7078	0.045*
H19B	0.2124	0.0627	0.7332	0.045*
H19C	0.2225	0.0851	0.6582	0.045*
C20	0.2346 (4)	0.44415 (14)	0.52139 (13)	0.0294 (6)
H20	0.2982	0.4771	0.5525	0.035*
C21	0.3977 (5)	0.41495 (16)	0.47722 (15)	0.0417 (7)
H21A	0.4621	0.4525	0.4534	0.050*
H21B	0.3386	0.3827	0.4461	0.050*
H21C	0.4968	0.3910	0.5039	0.050*
C22	0.0797 (5)	0.48390 (14)	0.48107 (14)	0.0339 (7)
H22A	−0.0002	0.4505	0.4558	0.041*
H22B	−0.0116	0.5078	0.5114	0.041*
C23	0.1663 (5)	0.53685 (16)	0.43382 (15)	0.0412 (8)
H23A	0.2550	0.5129	0.4027	0.049*
H23B	0.2488	0.5697	0.4589	0.049*
C24	0.0101 (6)	0.57747 (17)	0.39493 (15)	0.0454 (8)
H24	−0.0784	0.5436	0.3725	0.054*
C25	−0.1188 (6)	0.62273 (18)	0.43633 (17)	0.0471 (8)
C26	−0.3137 (7)	0.6268 (3)	0.4248 (2)	0.0811 (14)
H26A	−0.3941	0.6572	0.4497	0.097*
H26B	−0.3722	0.5992	0.3917	0.097*
C27	−0.0217 (6)	0.66514 (19)	0.48788 (17)	0.0543 (9)
H27A	−0.1183	0.6979	0.5056	0.065*
H27B	0.0908	0.6902	0.4690	0.065*
H27C	0.0262	0.6352	0.5229	0.065*
C28	0.1132 (7)	0.6206 (2)	0.34208 (17)	0.0600 (11)
H28A	0.0124	0.6432	0.3150	0.072*
H28B	0.1955	0.5907	0.3147	0.072*
H28C	0.1975	0.6554	0.3628	0.072*
C29	0.5309 (6)	0.16468 (18)	0.90441 (16)	0.0489 (9)
H29A	0.4131	0.1864	0.9236	0.059*
H29B	0.6271	0.2001	0.8919	0.059*
H29C	0.5916	0.1337	0.9364	0.059*
C30	0.3232 (5)	0.06653 (16)	0.86562 (17)	0.0420 (8)
H30A	0.2018	0.0876	0.8830	0.050*
H30B	0.3857	0.0383	0.8995	0.050*
H30C	0.2894	0.0376	0.8281	0.050*
C31	−0.0734 (4)	0.26625 (14)	0.61295 (14)	0.0322 (6)
H31A	−0.1449	0.2965	0.5828	0.039*
H31B	−0.1674	0.2466	0.6444	0.039*
H31C	−0.0096	0.2292	0.5883	0.039*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0341 (12)	0.0587 (15)	0.0660 (16)	0.0023 (12)	−0.0095 (12)	0.0157 (13)
C1	0.0374 (17)	0.0334 (15)	0.0436 (18)	0.0087 (14)	0.0071 (15)	0.0081 (14)
C2	0.0351 (17)	0.0348 (15)	0.0529 (19)	0.0089 (14)	0.0042 (16)	0.0070 (14)
C3	0.0296 (16)	0.0305 (14)	0.0511 (17)	−0.0051 (13)	−0.0015 (14)	0.0173 (14)
C4	0.0299 (15)	0.0327 (14)	0.0362 (15)	−0.0002 (13)	−0.0024 (13)	0.0103 (12)
C5	0.0249 (14)	0.0276 (13)	0.0322 (14)	−0.0035 (12)	−0.0014 (12)	0.0056 (11)
C6	0.0352 (16)	0.0365 (15)	0.0336 (15)	0.0044 (14)	0.0031 (13)	0.0050 (12)
C7	0.0273 (14)	0.0334 (14)	0.0316 (14)	0.0039 (12)	0.0034 (13)	0.0025 (11)
C8	0.0216 (13)	0.0229 (12)	0.0308 (13)	−0.0022 (11)	−0.0018 (11)	−0.0032 (10)
C9	0.0243 (14)	0.0272 (13)	0.0277 (12)	0.0012 (11)	0.0000 (11)	0.0004 (11)
C10	0.0265 (14)	0.0275 (13)	0.0336 (14)	0.0013 (12)	0.0003 (12)	0.0020 (11)
C11	0.0396 (17)	0.0308 (14)	0.0298 (13)	0.0101 (14)	0.0041 (13)	−0.0005 (11)
C12	0.0348 (16)	0.0318 (14)	0.0301 (14)	0.0062 (13)	0.0036 (13)	0.0007 (12)
C13	0.0238 (13)	0.0256 (12)	0.0244 (12)	−0.0015 (11)	0.0012 (11)	−0.0016 (10)
C14	0.0213 (13)	0.0266 (12)	0.0280 (13)	−0.0010 (11)	0.0002 (11)	0.0013 (10)
C15	0.0225 (13)	0.0315 (14)	0.0333 (14)	0.0060 (12)	0.0037 (12)	0.0013 (12)
C16	0.0236 (13)	0.0293 (13)	0.0348 (14)	0.0027 (12)	0.0026 (12)	0.0023 (11)
C17	0.0242 (14)	0.0258 (12)	0.0268 (12)	0.0012 (11)	−0.0003 (11)	0.0018 (10)
C18	0.0254 (14)	0.0331 (14)	0.0356 (15)	−0.0031 (12)	−0.0029 (13)	−0.0001 (13)
C19	0.0395 (17)	0.0295 (14)	0.0439 (17)	−0.0045 (13)	−0.0063 (15)	−0.0005 (13)
C20	0.0293 (15)	0.0287 (13)	0.0302 (13)	−0.0028 (12)	0.0030 (12)	0.0009 (11)
C21	0.0418 (18)	0.0413 (16)	0.0419 (16)	0.0059 (16)	0.0115 (15)	0.0104 (14)
C22	0.0376 (17)	0.0299 (13)	0.0343 (15)	−0.0003 (13)	0.0017 (14)	0.0063 (12)
C23	0.0446 (19)	0.0379 (16)	0.0412 (17)	−0.0010 (15)	0.0044 (15)	0.0107 (14)
C24	0.060 (2)	0.0377 (16)	0.0381 (16)	−0.0077 (17)	−0.0018 (17)	0.0070 (14)
C25	0.049 (2)	0.0470 (18)	0.0452 (18)	0.0015 (17)	0.0032 (17)	0.0145 (16)
C26	0.054 (3)	0.114 (4)	0.075 (3)	0.006 (3)	−0.001 (2)	0.005 (3)
C27	0.062 (2)	0.0481 (19)	0.053 (2)	0.0064 (19)	0.004 (2)	0.0004 (17)
C28	0.080 (3)	0.054 (2)	0.0456 (19)	0.006 (2)	0.016 (2)	0.0181 (17)
C29	0.055 (2)	0.0503 (19)	0.0419 (18)	0.0037 (18)	−0.0130 (17)	0.0045 (15)
C30	0.0334 (16)	0.0398 (17)	0.0527 (19)	0.0008 (14)	0.0029 (15)	0.0161 (15)
C31	0.0278 (15)	0.0324 (14)	0.0365 (15)	−0.0066 (12)	−0.0071 (13)	0.0033 (12)

Geometric parameters (Å, º) top

O1—C3	1.220 (4)	C17—C20	1.540 (4)
C1—C2	1.532 (4)	C17—H17	1.0000
C1—C10	1.533 (4)	C18—H18A	0.9800
C1—H1A	0.9900	C18—H18B	0.9800
C1—H1B	0.9900	C18—H18C	0.9800
C2—C3	1.499 (4)	C19—H19A	0.9800
C2—H2A	0.9900	C19—H19B	0.9800
C2—H2B	0.9900	C19—H19C	0.9800
C3—C4	1.524 (4)	C20—C21	1.532 (4)
C4—C29	1.533 (4)	C20—C22	1.538 (4)
C4—C30	1.551 (4)	C20—H20	1.0000
C4—C5	1.568 (4)	C21—H21A	0.9800
C5—C6	1.539 (4)	C21—H21B	0.9800
C5—C10	1.556 (4)	C21—H21C	0.9800
C5—H5	1.0000	C22—C23	1.530 (4)
C6—C7	1.499 (4)	C22—H22A	0.9900
C6—H6A	0.9900	C22—H22B	0.9900
C6—H6B	0.9900	C23—C24	1.538 (5)
C7—C8	1.330 (4)	C23—H23A	0.9900
C7—H7	0.9500	C23—H23B	0.9900
C8—C9	1.523 (4)	C24—C25	1.499 (5)
C8—C14	1.530 (4)	C24—C28	1.536 (4)
C9—C11	1.534 (4)	C24—H24	1.0000
C9—C10	1.559 (4)	C25—C26	1.333 (6)
C9—H9	1.0000	C25—C27	1.492 (5)
C10—C19	1.542 (4)	C26—H26A	0.9500
C11—C12	1.554 (4)	C26—H26B	0.9500
C11—H11A	0.9900	C27—H27A	0.9800
C11—H11B	0.9900	C27—H27B	0.9800
C12—C13	1.542 (4)	C27—H27C	0.9800
C12—H12A	0.9900	C28—H28A	0.9800
C12—H12B	0.9900	C28—H28B	0.9800
C13—C18	1.544 (4)	C28—H28C	0.9800
C13—C17	1.552 (4)	C29—H29A	0.9800
C13—C14	1.557 (4)	C29—H29B	0.9800
C14—C15	1.539 (4)	C29—H29C	0.9800
C14—C31	1.541 (4)	C30—H30A	0.9800
C15—C16	1.556 (4)	C30—H30B	0.9800
C15—H15A	0.9900	C30—H30C	0.9800
C15—H15B	0.9900	C31—H31A	0.9800
C16—C17	1.561 (4)	C31—H31B	0.9800
C16—H16A	0.9900	C31—H31C	0.9800
C16—H16B	0.9900

C2—C1—C10	113.1 (3)	H16A—C16—H16B	108.6
C2—C1—H1A	109.0	C20—C17—C13	120.2 (2)
C10—C1—H1A	109.0	C20—C17—C16	111.8 (2)
C2—C1—H1B	109.0	C13—C17—C16	103.1 (2)
C10—C1—H1B	109.0	C20—C17—H17	107.0
H1A—C1—H1B	107.8	C13—C17—H17	107.0
C3—C2—C1	109.3 (2)	C16—C17—H17	107.0
C3—C2—H2A	109.8	C13—C18—H18A	109.5
C1—C2—H2A	109.8	C13—C18—H18B	109.5
C3—C2—H2B	109.8	H18A—C18—H18B	109.5
C1—C2—H2B	109.8	C13—C18—H18C	109.5
H2A—C2—H2B	108.3	H18A—C18—H18C	109.5
O1—C3—C2	121.3 (3)	H18B—C18—H18C	109.5
O1—C3—C4	122.0 (3)	C10—C19—H19A	109.5
C2—C3—C4	116.7 (3)	C10—C19—H19B	109.5
C3—C4—C29	108.9 (3)	H19A—C19—H19B	109.5
C3—C4—C30	106.0 (2)	C10—C19—H19C	109.5
C29—C4—C30	108.2 (3)	H19A—C19—H19C	109.5
C3—C4—C5	110.1 (2)	H19B—C19—H19C	109.5
C29—C4—C5	108.8 (2)	C21—C20—C22	110.7 (2)
C30—C4—C5	114.8 (2)	C21—C20—C17	113.0 (2)
C6—C5—C10	109.8 (2)	C22—C20—C17	109.1 (2)
C6—C5—C4	112.9 (2)	C21—C20—H20	108.0
C10—C5—C4	118.4 (2)	C22—C20—H20	108.0
C6—C5—H5	104.8	C17—C20—H20	108.0
C10—C5—H5	104.8	C20—C21—H21A	109.5
C4—C5—H5	104.8	C20—C21—H21B	109.5
C7—C6—C5	112.1 (2)	H21A—C21—H21B	109.5
C7—C6—H6A	109.2	C20—C21—H21C	109.5
C5—C6—H6A	109.2	H21A—C21—H21C	109.5
C7—C6—H6B	109.2	H21B—C21—H21C	109.5
C5—C6—H6B	109.2	C23—C22—C20	115.0 (3)
H6A—C6—H6B	107.9	C23—C22—H22A	108.5
C8—C7—C6	124.2 (3)	C20—C22—H22A	108.5
C8—C7—H7	117.9	C23—C22—H22B	108.5
C6—C7—H7	117.9	C20—C22—H22B	108.5
C7—C8—C9	121.3 (2)	H22A—C22—H22B	107.5
C7—C8—C14	122.3 (2)	C22—C23—C24	114.5 (3)
C9—C8—C14	116.4 (2)	C22—C23—H23A	108.6
C8—C9—C11	111.8 (2)	C24—C23—H23A	108.6
C8—C9—C10	111.8 (2)	C22—C23—H23B	108.6
C11—C9—C10	114.5 (2)	C24—C23—H23B	108.6
C8—C9—H9	106.0	H23A—C23—H23B	107.6
C11—C9—H9	106.0	C25—C24—C28	109.8 (3)
C10—C9—H9	106.0	C25—C24—C23	113.8 (3)
C1—C10—C19	110.2 (2)	C28—C24—C23	109.8 (3)
C1—C10—C5	108.8 (2)	C25—C24—H24	107.7
C19—C10—C5	113.4 (2)	C28—C24—H24	107.7
C1—C10—C9	109.1 (2)	C23—C24—H24	107.7
C19—C10—C9	110.4 (2)	C26—C25—C27	121.5 (4)
C5—C10—C9	104.8 (2)	C26—C25—C24	120.1 (4)
C9—C11—C12	113.7 (2)	C27—C25—C24	118.3 (3)
C9—C11—H11A	108.8	C25—C26—H26A	120.0
C12—C11—H11A	108.8	C25—C26—H26B	120.0
C9—C11—H11B	108.8	H26A—C26—H26B	120.0
C12—C11—H11B	108.8	C25—C27—H27A	109.5
H11A—C11—H11B	107.7	C25—C27—H27B	109.5
C13—C12—C11	114.7 (2)	H27A—C27—H27B	109.5
C13—C12—H12A	108.6	C25—C27—H27C	109.5
C11—C12—H12A	108.6	H27A—C27—H27C	109.5
C13—C12—H12B	108.6	H27B—C27—H27C	109.5
C11—C12—H12B	108.6	C24—C28—H28A	109.5
H12A—C12—H12B	107.6	C24—C28—H28B	109.5
C12—C13—C18	111.0 (2)	H28A—C28—H28B	109.5
C12—C13—C17	116.0 (2)	C24—C28—H28C	109.5
C18—C13—C17	108.2 (2)	H28A—C28—H28C	109.5
C12—C13—C14	109.3 (2)	H28B—C28—H28C	109.5
C18—C13—C14	110.4 (2)	C4—C29—H29A	109.5
C17—C13—C14	101.6 (2)	C4—C29—H29B	109.5
C8—C14—C15	117.7 (2)	H29A—C29—H29B	109.5
C8—C14—C31	107.8 (2)	C4—C29—H29C	109.5
C15—C14—C31	106.4 (2)	H29A—C29—H29C	109.5
C8—C14—C13	110.4 (2)	H29B—C29—H29C	109.5
C15—C14—C13	101.7 (2)	C4—C30—H30A	109.5
C31—C14—C13	112.7 (2)	C4—C30—H30B	109.5
C14—C15—C16	103.6 (2)	H30A—C30—H30B	109.5
C14—C15—H15A	111.0	C4—C30—H30C	109.5
C16—C15—H15A	111.0	H30A—C30—H30C	109.5
C14—C15—H15B	111.0	H30B—C30—H30C	109.5
C16—C15—H15B	111.0	C14—C31—H31A	109.5
H15A—C15—H15B	109.0	C14—C31—H31B	109.5
C15—C16—C17	107.1 (2)	H31A—C31—H31B	109.5
C15—C16—H16A	110.3	C14—C31—H31C	109.5
C17—C16—H16A	110.3	H31A—C31—H31C	109.5
C15—C16—H16B	110.3	H31B—C31—H31C	109.5
C17—C16—H16B	110.3

C10—C1—C2—C3	−60.6 (3)	C11—C12—C13—C17	−147.3 (2)
C1—C2—C3—O1	−123.0 (3)	C11—C12—C13—C14	−33.2 (3)
C1—C2—C3—C4	56.2 (3)	C7—C8—C14—C15	32.7 (4)
O1—C3—C4—C29	14.7 (4)	C9—C8—C14—C15	−150.2 (2)
C2—C3—C4—C29	−164.5 (2)	C7—C8—C14—C31	−87.6 (3)
O1—C3—C4—C30	−101.4 (3)	C9—C8—C14—C31	89.5 (3)
C2—C3—C4—C30	79.4 (3)	C7—C8—C14—C13	148.8 (3)
O1—C3—C4—C5	133.9 (3)	C9—C8—C14—C13	−34.0 (3)
C2—C3—C4—C5	−45.3 (3)	C12—C13—C14—C8	63.0 (3)
C3—C4—C5—C6	170.2 (2)	C18—C13—C14—C8	−59.3 (3)
C29—C4—C5—C6	−70.6 (3)	C17—C13—C14—C8	−173.9 (2)
C30—C4—C5—C6	50.7 (3)	C12—C13—C14—C15	−171.2 (2)
C3—C4—C5—C10	39.9 (3)	C18—C13—C14—C15	66.5 (3)
C29—C4—C5—C10	159.1 (3)	C17—C13—C14—C15	−48.2 (2)
C30—C4—C5—C10	−79.6 (3)	C12—C13—C14—C31	−57.7 (3)
C10—C5—C6—C7	−46.4 (3)	C18—C13—C14—C31	−180.0 (2)
C4—C5—C6—C7	179.1 (2)	C17—C13—C14—C31	65.4 (3)
C5—C6—C7—C8	13.1 (4)	C8—C14—C15—C16	159.4 (2)
C6—C7—C8—C9	−1.8 (4)	C31—C14—C15—C16	−79.6 (2)
C6—C7—C8—C14	175.2 (3)	C13—C14—C15—C16	38.6 (3)
C7—C8—C9—C11	154.0 (3)	C14—C15—C16—C17	−14.9 (3)
C14—C8—C9—C11	−23.2 (3)	C12—C13—C17—C20	−78.1 (3)
C7—C8—C9—C10	24.2 (4)	C18—C13—C17—C20	47.3 (3)
C14—C8—C9—C10	−153.0 (2)	C14—C13—C17—C20	163.5 (2)
C2—C1—C10—C19	−70.5 (3)	C12—C13—C17—C16	156.6 (2)
C2—C1—C10—C5	54.3 (3)	C18—C13—C17—C16	−78.0 (2)
C2—C1—C10—C9	168.1 (3)	C14—C13—C17—C16	38.2 (2)
C6—C5—C10—C1	−176.6 (2)	C15—C16—C17—C20	−145.2 (2)
C4—C5—C10—C1	−44.9 (3)	C15—C16—C17—C13	−14.6 (3)
C6—C5—C10—C19	−53.6 (3)	C13—C17—C20—C21	52.2 (3)
C4—C5—C10—C19	78.1 (3)	C16—C17—C20—C21	173.3 (2)
C6—C5—C10—C9	66.9 (3)	C13—C17—C20—C22	175.7 (2)
C4—C5—C10—C9	−161.5 (2)	C16—C17—C20—C22	−63.2 (3)
C8—C9—C10—C1	−171.0 (2)	C21—C20—C22—C23	−49.9 (3)
C11—C9—C10—C1	60.5 (3)	C17—C20—C22—C23	−174.8 (2)
C8—C9—C10—C19	67.7 (3)	C20—C22—C23—C24	−178.6 (3)
C11—C9—C10—C19	−60.7 (3)	C22—C23—C24—C25	65.2 (4)
C8—C9—C10—C5	−54.7 (3)	C22—C23—C24—C28	−171.3 (3)
C11—C9—C10—C5	176.9 (2)	C28—C24—C25—C26	98.2 (5)
C8—C9—C11—C12	53.3 (3)	C23—C24—C25—C26	−138.3 (4)
C10—C9—C11—C12	−178.2 (2)	C28—C24—C25—C27	−78.8 (4)
C9—C11—C12—C13	−23.7 (4)	C23—C24—C25—C27	44.7 (4)
C11—C12—C13—C18	88.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···O1ⁱ	0.99	2.55	3.528 (4)	169

Symmetry code: (i) −x+1, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₃₁H₅₀O
M_r	438.71
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	173
a, b, c (Å)	6.7207 (1), 19.4804 (5), 20.5035 (5)
V (Å³)	2684.36 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.06
Crystal size (mm)	0.30 × 0.05 × 0.04

Data collection
Diffractometer	Nonius APEXII CCD diffractometer
Absorption correction	Multi-scan (SORTAV; Blessing, 1997)
T_min, T_max	0.981, 0.997
No. of measured, independent and observed [I > 2σ(I)] reflections	6101, 3485, 2918
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.122, 1.15
No. of reflections	3485
No. of parameters	297
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.20

Computer programs: COLLECT (Nonius, 1998), HKL DENZO (Otwinowski & Minor, 1997), SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···O1ⁱ	0.99	2.55	3.528 (4)	169

Symmetry code: (i) −x+1, y+1/2, −z+3/2.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Blessing, R. H. (1997). J. Appl. Cryst. 30, 421–426. CrossRef CAS Web of Science IUCr Journals Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Hussain, N., Habib-ur-Rehman, & Parvez, M. (2009). Acta Cryst. E65, o1202. Google Scholar
Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Schun, Y., Cordell, G. A., Cox, P. J. & Howie, R. A. (1986). Phytochemistry, 25, 753–755. CSD CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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