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Volume 68 
Part 12 
Pages o3413-o3414  
December 2012  

Received 5 November 2012
Accepted 12 November 2012
Online 24 November 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.036
wR = 0.090
Data-to-parameter ratio = 16.2
Details
Open access

(25R)-6[alpha]-Hydroxy-5[alpha]-spirostan-3[beta]-yl tosylate

aBenemérita Universidad Autónoma de Puebla, Facultad de Ciencias Químicas, Ciudad Universitaria, Puebla, Pue. 72570, Mexico,bUniversidad Autónoma de Nuevo León, UANL, Facultad de Ciencias Químicas, Av. Universidad S/N, Ciudad Universitaria, San Nicolás de los Garza, Nuevo León CP 66451, Mexico,cHerbario y Jardín Botánico, Benemérita Universidad Autónoma de Puebla, Ciudad Universitaria, Puebla, Pue. 72570, Mexico, and dEscuelas de Ingeniería en Petróleos e Ingeniería Química, Universidad del Istmo, Ciudad Universitaria s/n, 70760 Sto. Domingo Tehuantepec, Oax., Mexico
Correspondence e-mail: sylvain_bernes@hotmail.com

The title steroid, C34H50O6S, is an intermediate on the synthetic route between diosgenin and brassinosteroids, which possess the A ring modified with the 2[alpha],3[alpha]-diol functionality. The polycyclic spirostan system has the expected conformation, with six-membered rings adopting chair forms and the five-membered rings envelope forms (flap atoms are the methine C atom in the C/D-ring junction and the spiro C atom connecting rings E and F). The 3[beta]-tosylate group is oriented in such a way that S=O bonds are engaged in intermolecular hydrogen bonds with O-H and C-H donors. Chains of molecules are formed along [100] via O-H...O hydrogen bonds, and secondary weak C-H...O interactions connect two neighbouring chains in the [001] direction.

Related literature

For background to brassinosteroids, see: Asami et al. (2005[Asami, T., Nakano, T. & Fujioka, S. (2005). Vitam. Horm. 72, 479-504.]); Kang & Guo (2011[Kang, Y. Y. & Guo, S. R. (2011). Brassinosteroids: A Class of Plant Hormone, edited by S. Hayat & A. Ahmad, pp. 269-288. Dordrecht: Springer.]); Zullo & Adam (2002[Zullo, M. A. T. & Adam, G. (2002). Braz. J. Plant Physiol. 14, 143-181.]). For the hydroboration-oxidation synthetic step used for the preparation of the title compound, see: Smith & Pelter (1991[Smith, K. & Pelter, A. (1991). Comprehensive Organic Synthesis, Vol. 8, edited by B. M. Trost & I. Fleming, pp. 703-731. Oxford: Pergamon Press.]); Brown (1962[Brown, H. C. (1962). Hydroboration, pp. 12-13. New York: W. A. Benjamin Inc.]). For the structure of another steroid functionalized at C-3 with a tosylate group, see: Cox et al. (1996[Cox, P. J., Buchanan, H. J. & Wardell, J. L. (1996). Acta Cryst. C52, 2111-2113.]).

[Scheme 1]

Experimental

Crystal data
  • C34H50O6S

  • Mr = 586.80

  • Orthorhombic, P 21 21 21

  • a = 6.7653 (8) Å

  • b = 12.2856 (11) Å

  • c = 37.943 (4) Å

  • V = 3153.6 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.15 mm-1

  • T = 296 K

  • 0.6 × 0.5 × 0.4 mm

Data collection
  • Bruker P4 diffractometer

  • Absorption correction: [psi] scan (XSCANS; Siemens, 1996[Siemens (1996). XSCANS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]) Tmin = 0.905, Tmax = 0.943

  • 9218 measured reflections

  • 6167 independent reflections

  • 5274 reflections with I > 2[sigma](I)

  • Rint = 0.023

  • 3 standard reflections every 97 reflections intensity decay: 1.5%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.036

  • wR(F2) = 0.090

  • S = 1.03

  • 6167 reflections

  • 380 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.16 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 2504 Friedel pairs

  • Flack parameter: -0.03 (7)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O30-H30...O33i 0.78 (3) 2.35 (3) 3.098 (2) 159 (3)
C40-H40A...O34ii 0.93 2.65 3.352 (3) 133
Symmetry codes: (i) x-1, y, z; (ii) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+2].

Data collection: XSCANS (Siemens, 1996[Siemens (1996). XSCANS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BQ2379 ).


Acknowledgements

The authors thank CONACYT for the Repatriation grant 166040 and PROMEP for the grant PROMEP/103.5/12/4367 BUAP-PTC-301.

References

Asami, T., Nakano, T. & Fujioka, S. (2005). Vitam. Horm. 72, 479-504.  [CrossRef] [PubMed] [ChemPort]
Brown, H. C. (1962). Hydroboration, pp. 12-13. New York: W. A. Benjamin Inc.
Cox, P. J., Buchanan, H. J. & Wardell, J. L. (1996). Acta Cryst. C52, 2111-2113.  [CSD] [CrossRef] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Kang, Y. Y. & Guo, S. R. (2011). Brassinosteroids: A Class of Plant Hormone, edited by S. Hayat & A. Ahmad, pp. 269-288. Dordrecht: Springer.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Siemens (1996). XSCANS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
Smith, K. & Pelter, A. (1991). Comprehensive Organic Synthesis, Vol. 8, edited by B. M. Trost & I. Fleming, pp. 703-731. Oxford: Pergamon Press.
Zullo, M. A. T. & Adam, G. (2002). Braz. J. Plant Physiol. 14, 143-181.  [CrossRef] [ChemPort]


Acta Cryst (2012). E68, o3413-o3414   [ doi:10.1107/S1600536812046600 ]

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