24-Methyl­lanosta-7,25-dien-3-one

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

doi:10.1107/S1600536810005118

Volume 66
Part 3
Page o626
March 2010

Received 17 January 2010
Accepted 8 February 2010
Online 13 February 2010

Key indicators
Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.004 Å
R = 0.055
wR = 0.122
Data-to-parameter ratio = 11.7
Details

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

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[ [alpha] ]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-HO 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 K radiation
= 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 > 2(I)
R_int = 0.036

Refinement

R[F² > 2(F²)] = 0.055
wR(F²) = 0.122
S = 1.15
3485 reflections
297 parameters
H-atom parameters constrained
_max = 0.21 e Å^-3
_min = -0.20 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C16-H16AO1ⁱ	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.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2983 ).

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.
Blessing, R. H. (1997). J. Appl. Cryst. 30, 421-426.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Hussain, N., Habib-ur-Rehman, & Parvez, M. (2009). Acta Cryst. E65, o1202.
Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.
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.
Schun, Y., Cordell, G. A., Cox, P. J. & Howie, R. A. (1986). Phytochemistry, 25, 753-755.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds