(IUCr) (E)-17[beta],19-Epoxymethano-17,23,24-tridemethyl-4-nor-5[beta],18[alpha]-olean-3-one oxime

Volume 65
Part 6
Page o1262
June 2009

Received 21 January 2009
Accepted 4 May 2009
Online 14 May 2009

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.031
wR = 0.094
Data-to-parameter ratio = 9.3
Details

(E)-17,19-Epoxymethano-17,23,24-tridemethyl-4-nor-5,18-olean-3-one oxime

Anna Froelich,^a Oxana B. Kazakova,^b Genrikh Tolstikov ^b and Andrzej K. Gzella ^a ^*

^aDepartment of Organic Chemistry, Poznan University of Medical Sciences, ul. Grunwaldzka 6, 60-780 Poznan, Poland, and ^bInstitute of Organic Chemistry, Ufa Research Center of the Russian Academy of Sciences, 71, prosp. Oktyabrya, 450054 Ufa, Russian Federation
Correspondence e-mail: akgzella@ump.edu.pl

In the pentacyclic triterpenoide skeleton of the title molecule, C₂₇H₄₃NO₂ [systematic name: (3E,3aS,5aR,5bR,7aR,11R,11aR,11bR,13aR,13bR)-5a,5b,10,10,13b-pentamethylicosahydro-1H-11,7a-(epoxymethano)cyclopenta[a]chrysen-3-one oxime], the five-membered ring A has an envelope conformation, while the six-membered rings B-E adopt chair conformations. Rings A and B are cis-fused. The hydroximino group has an E configuration. Strong intermolecular O-HO hydrogen bonds link the molecules into helical chains.

Related literature

For the syntheses of related compounds, see: Medvedeva et al. (2004, 2006); Gzella et al. (1997, 1998); Zaprutko (1995, 1997). For a description of the Cambridge Structural Database, see: Allen (2002). For puckering parameters, see: Cremer & Pople (1975); Spek (2009).

Experimental

Crystal data

C₂₇H₄₃NO₂
M_r = 413.62
Orthorhombic, P 2₁ 2₁ 2₁
a = 12.5887 (16) Å
b = 13.2550 (11) Å
c = 14.5355 (12) Å
V = 2425.4 (4) Å³
Z = 4
Cu K radiation
= 0.53 mm^-1
T = 293 K
0.40 × 0.22 × 0.13 mm

Data collection

Kuma Diffraction KM-4 diffractometer
Absorption correction: none
4994 measured reflections
2610 independent reflections
2240 reflections with I > 2(I)
R_int = 0.037
3 standard reflections every 100 reflections intensity decay: 2.3%

Refinement

R[F² > 2(F²)] = 0.031
wR(F²) = 0.094
S = 1.06
2610 reflections
281 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.12 e Å^-3
_min = -0.12 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1O2ⁱ	0.87 (3)	1.93 (3)	2.782 (2)	164 (3)
Symmetry code: (i) $[-x+{\script{1\over 2}}, -y+2, z+{\script{1\over 2}}]$ .

Data collection: KM-4 Software (Kuma Diffraction, 1996 $[Kuma Diffraction (1996). KM-4 Software. Kuma Diffraction, Wroclaw, Poland.]$ ); cell refinement: KM-4 Software; data reduction: KM-4 Software; 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: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FB2138 ).

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Gzella, A., Zaprutko, L. & Wrzeciono, U. (1997). Acta Cryst. C53, 261-264.
Gzella, A., Zaprutko, L. & Wrzeciono, U. (1998). Acta Cryst. C54, 1309-1312.
Kuma Diffraction (1996). KM-4 Software. Kuma Diffraction, Wroclaw, Poland.
Medvedeva, N. I., Flekhter, O. B., Gzella, A. & Zaprutko, L. (2006). Chem. Nat. Comp. 42, 618-619.
Medvedeva, N. I., Flekhter, O. B., Tretyakova, E. V., Galin, F. Z., Baltina, L. A., Spirikhin, L. V. & Tolstikov, G. A. (2004). Russ. J. Org. Chem. 40, 1092-1097.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Zaprutko, L. (1995). Pol. J. Chem. 69, 1003-1012.
Zaprutko, L. (1997). Pol. J. Chem. 71, 1499-1501.

organic compounds