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Volume 69 
Part 10 
Page o1555  
October 2013  

Received 29 July 2013
Accepted 10 September 2013
Online 18 September 2013

Key indicators
Single-crystal X-ray study
T = 120 K
Mean [sigma](C-C) = 0.002 Å
R = 0.041
wR = 0.108
Data-to-parameter ratio = 22.0
Details
Open access

rac-Methyl (3aR*,4S*,5R*,7aR*)-5,7a-bis(acetyloxy)-3-oxo-2-phenyloctahydro-1H-isoindole-4-carboxylate

aDepartment of Chemistry, University of Douala, Faculty of Sciences, PO Box 24157, Douala, Republic of , Cameroon,bOrganic Chemistry Department, Peoples' Friendship University of Russia, Miklukho-Maklaya St. 6, Moscow, 117198, Russian Federation, and cX-Ray Structural Centre, A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov St, B-334, Moscow 119991, Russian Federation
Correspondence e-mail: vkh@xray.ineos.ac.ru

The title molecule, C20H23NO7, the product of nucleophilic cleavage of the 3a,6-epoxy bridge in 1-oxo-2-phenyloctahydro-3a,6-epoxyisoindole-7-carboxylate, comprises a cis-fused bicyclic system containing a 2-pyrrolidinone ring in an envelope conformation (with the C atom bearing the carboxylate substituent as the flap) and a cyclohexane ring in a chair conformation. The carboxylate substituent occupies the equatorial position, whereas the two acetyloxy substituents are in axial positions. The N atom has a trigonal-planar geometry, the sum of the bond angles being 359.3 (3)°. The dihedral angle between the mean plane of the four planar atoms of the pyrrolidinone ring and the phenyl ring is 25.98 (6)°. In the crystal, molecules are linked into zigzag chains along the c-axis direction by C-H...O hydrogen bonds.

Related literature

For the synthesis of 3a,6-epoxyisoindoles by intramolecular Diels-Alder reactions of furan, see: Vogel et al. (1999[Vogel, P., Cossy, J., Plumet, J. & Arjona, O. (1999). Tetrahedron, 55, 13521-13642.]); Zubkov et al. (2005[Zubkov, F. I., Nikitina, E. V. & Varlamov, A. V. (2005). Russ. Chem. Rev. 74, 639-669.]). For the synthesis of 2-phenyloctahydroisoindoles and their analogues, see: Balthaser et al. (2011[Balthaser, B. R., Maloney, M. C., Beeler, A. B., Porco, J. A. Jr & Snyder, J. K. (2011). Nat. Chem. 3, 969-973.]); Zubkov et al. (2011[Zubkov, F. I., Zaytsev, V. P., Nikitina, E. V., Boltukhina, E. V., Varlamov, A. V., Khrustalev, V. N. & Gozun, S. V. (2011). Tetrahedron, 67, 9148-9163.]). For related compounds, see: Zubkov et al. (2009[Zubkov, F. I., Ershova, J. D., Orlova, A. A., Zaytsev, V. P., Nikitina, E. V., Peregudov, A. S., Gurbanov, A. V., Borisov, R. S., Khrustalev, V. N., Maharramov, A. M. & Varlamov, A. V. (2009). Tetrahedron, 65, 3789-3803.], 2012[Zubkov, F. I., Zaytsev, V. P., Puzikova, E. S., Nikitina, E. V., Varlamov, A. V., Khrustalev, V. N. & Novikov, R. A. (2012). Chem. Heterocycl. Compd, 48, 514-524.]); Claeys et al. (2010[Claeys, D. D., Stevens, C. V., Roman, B. I., Caveye, P. van D., Waroquier, M. & Speybroeck, V. V. (2010). Org. Biomol. Chem. 8, 3644-3654.]).

[Scheme 1]

Experimental

Crystal data
  • C20H23NO7

  • Mr = 389.39

  • Monoclinic, C 2/c

  • a = 12.3802 (7) Å

  • b = 18.3516 (10) Å

  • c = 17.3596 (9) Å

  • [beta] = 102.749 (1)°

  • V = 3846.8 (4) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 120 K

  • 0.24 × 0.20 × 0.18 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS, Bruker, 2003[Bruker (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.976, Tmax = 0.982

  • 24538 measured reflections

  • 5633 independent reflections

  • 4521 reflections with I > 2[sigma](I)

  • Rint = 0.031

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.108

  • S = 1.04

  • 5633 reflections

  • 256 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.34 e Å-3

  • [Delta][rho]min = -0.27 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C3A-H3A...O3i 1.00 2.55 3.4135 (13) 144
C12-H12...O2ii 0.95 2.46 3.2812 (15) 145
Symmetry codes: (i) [-x+1, y, -z+{\script{3\over 2}}]; (ii) -x+1, -y, -z+1.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AA2096 ).


Acknowledgements

The authors are grateful to the Russian Foundation for Basic Research for financial support of this work (grant No. 12-03-31088-a).

References

Balthaser, B. R., Maloney, M. C., Beeler, A. B., Porco, J. A. Jr & Snyder, J. K. (2011). Nat. Chem. 3, 969-973.  [CrossRef] [ChemPort] [PubMed]
Bruker (2001). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Claeys, D. D., Stevens, C. V., Roman, B. I., Caveye, P. van D., Waroquier, M. & Speybroeck, V. V. (2010). Org. Biomol. Chem. 8, 3644-3654.  [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Vogel, P., Cossy, J., Plumet, J. & Arjona, O. (1999). Tetrahedron, 55, 13521-13642.  [Web of Science] [CrossRef] [ChemPort]
Zubkov, F. I., Ershova, J. D., Orlova, A. A., Zaytsev, V. P., Nikitina, E. V., Peregudov, A. S., Gurbanov, A. V., Borisov, R. S., Khrustalev, V. N., Maharramov, A. M. & Varlamov, A. V. (2009). Tetrahedron, 65, 3789-3803.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Zubkov, F. I., Nikitina, E. V. & Varlamov, A. V. (2005). Russ. Chem. Rev. 74, 639-669.  [CrossRef] [ChemPort]
Zubkov, F. I., Zaytsev, V. P., Nikitina, E. V., Boltukhina, E. V., Varlamov, A. V., Khrustalev, V. N. & Gozun, S. V. (2011). Tetrahedron, 67, 9148-9163.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Zubkov, F. I., Zaytsev, V. P., Puzikova, E. S., Nikitina, E. V., Varlamov, A. V., Khrustalev, V. N. & Novikov, R. A. (2012). Chem. Heterocycl. Compd, 48, 514-524.  [Web of Science] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o1555  [ doi:10.1107/S1600536813025129 ]

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