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Volume 69 
Part 7 
Page o1100  
July 2013  

Received 27 May 2013
Accepted 3 June 2013
Online 15 June 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.005 Å
R = 0.051
wR = 0.142
Data-to-parameter ratio = 13.4
Details
Open access

(-)-Norfluorocurarine ethanol monosolvate

aS.Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of Uzbekistan, Mirzo Ulugbek Str., 77, Tashkent 100170, Uzbekistan,bInstitute of Bioorganic Chemistry, Academy of Sciences of Uzbekistan, Mirzo Ulugbek Str., 83, Tashkent 100125, Uzbekistan, and cTashkent Institute of Irrigation and Melioration, Kori-Niyoziy Str., 39, Tashkent, 100000, Uzbekistan
Correspondence e-mail: adizovshahobiddin@yahoo.com

The title compound, C19H20N2O·C2H5OH, is an ethanol solvate of an indol alkaloid which was extracted from the plant Vinca erecta. The fused piperidine ring adopts an approximate boat conformation and the pyrrolidine ring an envelope conformation with one of the methylene C atoms at the flap. An intramolecular N-H...O hydrogen bond forms an S6 ring motif. In the crystal, norfulorocurarine and ethanol molecules are linked into a chain along the c-axis direction through N-H...O and O-H...N hydrogen bonds.

Related literature

For the biological activity of plants containing norfluorocurarine class alkaloids, see: Lavrenova & Lavrenov (1997[Lavrenova, G. V. & Lavrenov, V. K. (1997). Entsiklopedia lekarstvennykh rastenii, Vol. 1. Ukraine: Donnechina.]). For the isolation of norfluorocurarine from the plant Vinca erecta, see: Yunusov & Yuldashev (1952[Yunusov, S. Yu. & Yuldashev, P. Kh. (1952). Dokl. Akad. Nauk Uzbekiskoi SSR, 12, 24-27.], 1957[Yunusov, S. Yu. & Yuldashev, P. Kh. (1957). Zh. Obshch. Khim. 27, 2015-2018.]). For the physical properties and crystal structures of several norfluorocurarine solvates, see: Tashkhodjaev et al. (2011[Tashkhodjaev, B., Turgunov, K. K., Yuldashev, P. Kh. & Mirzaeva, M. M. (2011). Chem. Nat. Compd. 47, 531-535.]).

[Scheme 1]

Experimental

Crystal data
  • C19H20N2O·C2H6O

  • Mr = 338.44

  • Orthorhombic, P 21 21 21

  • a = 7.0138 (5) Å

  • b = 16.090 (1) Å

  • c = 16.490 (2) Å

  • V = 1860.9 (3) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 0.62 mm-1

  • T = 293 K

  • 0.60 × 0.30 × 0.20 mm

Data collection
  • Oxford Xcalibur, Ruby diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]) Tmin = 0.801, Tmax = 0.884

  • 5608 measured reflections

  • 3178 independent reflections

  • 2393 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.051

  • wR(F2) = 0.142

  • S = 0.99

  • 3178 reflections

  • 237 parameters

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

  • [Delta][rho]max = 0.33 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O1 0.87 (3) 2.31 (3) 2.785 (4) 115 (3)
N1-H1...O2 0.87 (3) 2.17 (3) 2.961 (4) 152 (3)
O2-H2...N4i 0.96 (5) 1.85 (5) 2.805 (4) 172 (5)
Symmetry code: (i) [-x+{\script{1\over 2}}, -y+1, z-{\script{1\over 2}}].

Data collection: CrysAlis PRO (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXS97 (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: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5277 ).


Acknowledgements

We thank the Academy of Sciences of the Republic of Uzbekistan for supporting this study (grant No. FA-F7-T185)

References

Lavrenova, G. V. & Lavrenov, V. K. (1997). Entsiklopedia lekarstvennykh rastenii, Vol. 1. Ukraine: Donnechina.
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Tashkhodjaev, B., Turgunov, K. K., Yuldashev, P. Kh. & Mirzaeva, M. M. (2011). Chem. Nat. Compd. 47, 531-535.
Yunusov, S. Yu. & Yuldashev, P. Kh. (1952). Dokl. Akad. Nauk Uzbekiskoi SSR, 12, 24-27.
Yunusov, S. Yu. & Yuldashev, P. Kh. (1957). Zh. Obshch. Khim. 27, 2015-2018.  [ChemPort]


Acta Cryst (2013). E69, o1100  [ doi:10.1107/S1600536813015365 ]

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