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Volume 69 
Part 5 
Page o635  
May 2013  

Received 27 January 2013
Accepted 17 March 2013
Online 5 April 2013

Key indicators
Single-crystal X-ray study
T = 113 K
Mean [sigma](C-C) = 0.002 Å
R = 0.029
wR = 0.066
Data-to-parameter ratio = 19.6
Details
Open access

(Z)-3[beta]-(2-Chloroanilino)-17(20)-pregnene

aCenter of Separation Technology, School of Chemical Engineering, University of Science and Technology Liaoning, Anshan 114051, People's Republic of China
Correspondence e-mail: hjy741110@yahoo.com.cn

In the pregnene fragment of the title compound, C27H38ClN, the three six-membered rings exhibit chair conformations and the five-membered ring has a distorted envelope form with the fused C atom not bearing a methyl group as the flap atom. The amino group is involved in the formation of an intramolecular N-H...Cl hydrogen bond. The crystal packing exhibits no short intermolecular contacts.

Related literature

For applications of pregnene-type steroidal alkaloid derivatives, see: Hua et al. (2005[Hua, Z. H., Carcache, D. A., Tian, Y., Li, Y.-M. & Danishiefsky, S. J. (2005). J. Org. Chem. 702, 9849-9856.]); Hunter & Priest (2006[Hunter, A. C. & Priest, S.-M. (2006). Steroids, 71, 30-33.]). For the crystal structure of the related compound (Z)-3[alpha]-(1,3-dioxoisoindolin-2-yl)-17 (20)-pregnene, see: Qi et al. (2011[Qi, Y., Qin, N. & Duan, H.-Q. (2011). Acta Cryst. E67, o2065.]).

[Scheme 1]

Experimental

Crystal data
  • C27H38ClN

  • Mr = 412.03

  • Monoclinic, P 21

  • a = 7.281 (1) Å

  • b = 17.467 (2) Å

  • c = 9.1310 (12) Å

  • [beta] = 106.447 (7)°

  • V = 1113.7 (2) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.19 mm-1

  • T = 113 K

  • 0.26 × 0.24 × 0.18 mm

Data collection
  • Rigaku Saturn724 CCD diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]) Tmin = 0.953, Tmax = 0.967

  • 14303 measured reflections

  • 5276 independent reflections

  • 4089 reflections with I > 2[sigma](I)

  • Rint = 0.038

Refinement
  • R[F2 > 2[sigma](F2)] = 0.029

  • wR(F2) = 0.066

  • S = 0.97

  • 5276 reflections

  • 269 parameters

  • 1 restraint

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

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 2537 Friedel pairs

  • Flack parameter: 0.02 (3)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H10...Cl1 0.875 (19) 2.50 (2) 2.9569 (13) 113.5 (16)

Data collection: CrystalClear (Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: CrystalStructure (Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV5384 ).


Acknowledgements

This project was supported by the Science and Technology Department of Liaoning Province Science Foundation (grant No. 2010226003), Graduate Education Innovation Program 2010.

References

Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Hua, Z. H., Carcache, D. A., Tian, Y., Li, Y.-M. & Danishiefsky, S. J. (2005). J. Org. Chem. 702, 9849-9856.  [CSD] [CrossRef]
Hunter, A. C. & Priest, S.-M. (2006). Steroids, 71, 30-33.  [CrossRef] [PubMed] [ChemPort]
Qi, Y., Qin, N. & Duan, H.-Q. (2011). Acta Cryst. E67, o2065.  [CrossRef] [details]
Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o635  [ doi:10.1107/S1600536813007290 ]

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