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Volume 69 
Part 2 
Pages o273-o274  
February 2013  

Received 5 January 2013
Accepted 15 January 2013
Online 23 January 2013

Key indicators
Single-crystal X-ray study
T = 120 K
Mean [sigma](C-C) = 0.001 Å
R = 0.044
wR = 0.127
Data-to-parameter ratio = 32.9
Details
Open access

(4R*,4aR*,7aS*)-5-Oxo-6-phenyl-4a,5,6,7,7a,8-hexahydro-4H-furo[2,3-f]isoindole-4-carboxylic acid

aDepartment of Organic Chemistry, Ivan Franko National University of Lviv, Kyryla and Mefodiya 6, Lviv 79005, Ukraine,bDepartment of Organic Chemistry, Peoples' Friendship University of Russia, 6 Miklukho-Maklaya St., Moscow 117198, Russian Federation,cFaculty of Chemistry, University of Wroclaw, 14 Joliot-Curie St, 50-383 Wroclaw, Poland, and dInstitute of Low Temperature and Structure Research, Okolna 2, 50-422 Wroclaw, Poland
Correspondence e-mail: horrak@gmail.com

The asymmetric unit of the title compound, C17H15NO4, contains two independent molecules with similar geometric parameters. In both molecules, the conformation of the cyclohexene ring is half-chair, while the pyrrolidinone ring adopts an envelope conformation with the [gamma]-carbon atom of the [alpha]-pyrrolidinone ring as the flap. In the crystal, O-H...O hydrogen bonds between the carboxylic and carbonyl groups link alternate independent molecules into chains propagating in the b-axis direction. The crystal packing also features weak C-H...[pi] interactions.

Related literature

For the intramolecular Diels-Alder reaction of vinylfuranes, see: Patre et al. (2007[Patre, E. R., Gawas, S., Sen, S., Parameswaran, P. S. & Tilve, S. G. (2007). Tetrahedron Lett. 48, 3517-3520.]). For related solid-phase Diels-Alder reaction with vinyl benzenes, see: Sun et al. (2000[Sun, S., Turchi, I. J., Xu, D. & Murray, W. V. (2000). J. Org. Chem. 65, 2555-2559.]). For palladium-catalysed tandem cyclization of allenes with heteroarylhalides, see: Ohno et al. (2005[Ohno, H., Miyamura, K., Mizutani, T., Kadoh, Y., Takeoka, Y., Hamaguchi, H. & Tanaka, T. (2005). Chem. Eur. J. 11, 3728-3741.]). For heterolignan derivatives, see: Ramos et al. (1999[Ramos, A. C., Pelaez-Lamamie de Clairac, R. & Medarde, M. (1999). Heterocycles, 51, 1443-1470.]); Leteurtre et al. (1992[Leteurtre, F., Madalengoitia, J., Orr, A., Guzi, T., Lehnert, E., MacDonald, T. & Pommier, Y. (1992). Cancer Res. 52, 4478-4483.]) and for their pharmaceutical properties, see: Iwasaki et al. (1996[Iwasaki, T., Kondo, K., Kuroda, T., Moritani, Y., Yamagata, S., Sugiura, M., Kikkawa, H., Kaminuma, O. & Ikezawa, K. (1996). J. Med. Chem. 39, 2696-2704.]); Ducharme et al. (1994[Ducharme, Y., Brideau, C., Dube, D., Chan, C. C., Falgueyret, J. P., Gillard, J. W., Guay, J., Hutchison, J. H., McFarlane, C. S., Riendeau, D., Scheigetz, J. & Girard, Y. (1994). J. Med. Chem. 37, 512-518.]). For a related structure, see: Obushak et al. (2011[Obushak, M. D., Horak, Y. I., Zaytsev, V. P., Motorygina, E. L., Zubkov, F. I. & Khrustalev, V. N. (2011). Acta Cryst. E67, o3031-o3032.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C17H15NO4

  • Mr = 297.30

  • Orthorhombic, P b c a

  • a = 12.107 (4) Å

  • b = 16.945 (5) Å

  • c = 27.370 (9) Å

  • V = 5615 (3) Å3

  • Z = 16

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 120 K

  • 0.64 × 0.42 × 0.28 mm

Data collection
  • Kuma KM-4-CCD diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Wroclaw, Poland.]) Tmin = 0.972, Tmax = 1.000

  • 84648 measured reflections

  • 13130 independent reflections

  • 9304 reflections with I > 2[sigma](I)

  • Rint = 0.030

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.127

  • S = 1.03

  • 13130 reflections

  • 399 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.54 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C13A-C18A and O1A-C5A rings, respectively.

D-H...A D-H H...A D...A D-H...A
O3B-H3B1...O4A 0.84 1.83 2.6517 (11) 165
O3A-H3A1...O4Bi 0.84 1.79 2.6329 (10) 178
C8A-H8A...Cg1ii 1.00 2.50 3.4710 (14) 165
C15A-H15A...Cg2iii 0.95 2.63 3.5470 (15) 162
C18A-H18B...Cg2iv 0.99 2.72 3.5492 (14) 141
Symmetry codes: (i) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]; (ii) [x+{\script{1\over 2}}, y, -z+{\script{3\over 2}}]; (iii) [-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iv) [x-{\script{1\over 2}}, y, -z+{\script{3\over 2}}].

Data collection: CrysAlis CCD (Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Wroclaw, Poland.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Wroclaw, Poland.]); data reduction: CrysAlis RED; 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: DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV5382 ).


Acknowledgements

The authors are grateful to the Ukrainian State Fund for Fundamental Research (grant No. F40.3/045) and the Russian Foundation for Basic Research (grant No. 11-03-90416) for the financial support of this work.

References

Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Ducharme, Y., Brideau, C., Dube, D., Chan, C. C., Falgueyret, J. P., Gillard, J. W., Guay, J., Hutchison, J. H., McFarlane, C. S., Riendeau, D., Scheigetz, J. & Girard, Y. (1994). J. Med. Chem. 37, 512-518.  [CrossRef] [ChemPort] [PubMed] [ISI]
Iwasaki, T., Kondo, K., Kuroda, T., Moritani, Y., Yamagata, S., Sugiura, M., Kikkawa, H., Kaminuma, O. & Ikezawa, K. (1996). J. Med. Chem. 39, 2696-2704.  [CrossRef] [ChemPort] [PubMed] [ISI]
Leteurtre, F., Madalengoitia, J., Orr, A., Guzi, T., Lehnert, E., MacDonald, T. & Pommier, Y. (1992). Cancer Res. 52, 4478-4483.  [PubMed] [ChemPort] [ISI]
Obushak, M. D., Horak, Y. I., Zaytsev, V. P., Motorygina, E. L., Zubkov, F. I. & Khrustalev, V. N. (2011). Acta Cryst. E67, o3031-o3032.  [CSD] [CrossRef] [details]
Ohno, H., Miyamura, K., Mizutani, T., Kadoh, Y., Takeoka, Y., Hamaguchi, H. & Tanaka, T. (2005). Chem. Eur. J. 11, 3728-3741.  [CrossRef] [PubMed] [ChemPort]
Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Wroclaw, Poland.
Patre, E. R., Gawas, S., Sen, S., Parameswaran, P. S. & Tilve, S. G. (2007). Tetrahedron Lett. 48, 3517-3520.  [ISI] [CrossRef] [ChemPort]
Ramos, A. C., Pelaez-Lamamie de Clairac, R. & Medarde, M. (1999). Heterocycles, 51, 1443-1470.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Sun, S., Turchi, I. J., Xu, D. & Murray, W. V. (2000). J. Org. Chem. 65, 2555-2559.  [CrossRef] [PubMed] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o273-o274   [ doi:10.1107/S160053681300144X ]

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