Triamcinolone acetonide acetate

Lu, X.; Tang, G.-P.; Gu, J.-M.; Hu, X.-R.

doi:10.1107/S1600536811000316

Volume 67
Part 2
Page o360
February 2011

Received 30 December 2010
Accepted 5 January 2011
Online 12 January 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.006 Å
R = 0.035
wR = 0.100
Data-to-parameter ratio = 7.2
Details

Triamcinolone acetonide acetate

Xiao Lu,^a Gu-Ping Tang,^a Jian-Ming Gu ^b and Xiu-Rong Hu ^b ^*

^aInstitute of Chemical Biology and Pharmaceutical Chemistry, Zhejiang University, Hangzhou, Zhejiang 310028, People's Republic of China, and ^bChemistry Department, Zhejiang University, Hangzhou, Zhejiang 310028, People's Republic of China
Correspondence e-mail: huxiurong@yahoo.com.cn

In the crystal structure of the title compound [systematic name: 2-(4b-fluoro-5-hydroxy-4a,6a,8,8-tetramethyl-2-oxo-2,4a,4b,5,6,6a,9a,10,10a,10b,11,12-dodecahydro-7,9-dioxapentaleno[2,1-a]phenanthren-6b-yl)-2-oxoethyl acetate], C₂₆H₃₃FO₇, the molecules are connected by intermolecular O-HO hydrogen bonds into an infinite supramolecular chain along the b axis. The molecular framework consists of five condensed rings, including three six-membered rings and two five-membered rings. The cyclohexa-2,5-dienone ring is nearly planar [maximum deviation = 0.013 (3) Å], while the cyclohexane rings adopt chair conformations. The two five-membered rings, viz. cyclopentane and 1,3-dioxolane, display envelope conformations.

Related literature

For applications of triamcinolone acetonide in medicine, see: Barnes (1998); Buttgereit (2000); Uckermann et al. (2005). For the crystal structures of related triamcinolone acetonide acetates, see: Suitchlmezian et al. (2006); Jess & Näther (2006).

Experimental

Crystal data

C₂₆H₃₃FO₇
M_r = 476.52
Monoclinic, P 2₁
a = 7.5460 (7) Å
b = 14.8102 (4) Å
c = 11.5773 (3) Å
= 109.905 (1)°
V = 1216.56 (12) Å³
Z = 2
Mo K radiation
= 0.10 mm^-1
T = 296 K
0.38 × 0.33 × 0.26 mm

Data collection

Rigaku R-AXIS RAPID/ZJUG diffractometer
9347 measured reflections
2216 independent reflections
1866 reflections with I > 2(I)
R_int = 0.027

Refinement

R[F² > 2(F²)] = 0.035
wR(F²) = 0.100
S = 1.00
2216 reflections
308 parameters
1 restraint
H-atom parameters constrained
_max = 0.18 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H201O1ⁱ	0.82	1.98	2.793 (4)	169
Symmetry code: (i) $[-x+2, y-{\script{1\over 2}}, -z+2]$ .

Data collection: PROCESS-AUTO (Rigaku, 2006); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku, 2007); 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: XU5133 ).

Acknowledgements

The project was supported by the Zhejiang Provincial Natural Science Foundation of China (J200801).

References

Barnes, P. J. (1998). Clin. Sci. 94, 557-572.
Buttgereit, F. (2000). Z. Rheumatol. 59, 119-123.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Jess, I. & Näther, C. (2006). Acta Cryst. E62, 0960-0962.
Rigaku (2006). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.
Rigaku (2007). CrystalStructure. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Suitchlmezian, V., Jess, I. & Näther, C. (2006). Acta Cryst. E62, 0788-0790.
Uckermann, O., Kutzera, F., Wolf, A., Pannicke, T., Reichenbach, A., Wiedemann, P., Wolf, S. & Bringmann, A. (2005). J. Pharmacol. Exp. Ther. 315, 1036-1045.

organic compounds

Triamcinolone acetonide acetate

Related literature

Experimental

Crystal data

Data collection

Refinement

Acknowledgements

References