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

Horak, Y.I.; Lytvyn, R.Z.; Zubkov, F.I.; Nikitina, E.V.; Homza, Y.V.; Lis, T.; Kinzhybalo, V.; Obushak, M.D.

doi:10.1107/S160053681300144X

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 (C-C) = 0.001 Å
R = 0.044
wR = 0.127
Data-to-parameter ratio = 32.9
Details

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

Yuriy I. Horak,^a ^* Roman Z. Lytvyn,^a Fedor I. Zubkov,^b Eugeniya V. Nikitina,^b Yuriy V. Homza,^a Tadeusz Lis,^c Vasyl Kinzhybalo ^d and Mykola D. Obushak ^a

^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-HO 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). For related solid-phase Diels-Alder reaction with vinyl benzenes, see: Sun et al. (2000). For palladium-catalysed tandem cyclization of allenes with heteroarylhalides, see: Ohno et al. (2005). For heterolignan derivatives, see: Ramos et al. (1999); Leteurtre et al. (1992) and for their pharmaceutical properties, see: Iwasaki et al. (1996); Ducharme et al. (1994). For a related structure, see: Obushak et al. (2011). For puckering parameters, see: Cremer & Pople (1975).

Experimental

Crystal data

C₁₇H₁₅NO₄
M_r = 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 radiation
= 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 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Wroclaw, Poland.]$ ) T_min = 0.972, T_max = 1.000
84648 measured reflections
13130 independent reflections
9304 reflections with I > 2(I)
R_int = 0.030

Refinement

R[F² > 2(F²)] = 0.044
wR(F²) = 0.127
S = 1.03
13130 reflections
399 parameters
H-atom parameters constrained
_max = 0.54 e Å^-3
_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-HA	D-H	HA	DA	D-HA
O3B-H3B1O4A	0.84	1.83	2.6517 (11)	165
O3A-H3A1O4Bⁱ	0.84	1.79	2.6329 (10)	178
C8A-H8ACg1ⁱⁱ	1.00	2.50	3.4710 (14)	165
C15A-H15ACg2ⁱⁱⁱ	0.95	2.63	3.5470 (15)	162
C18A-H18BCg2^iv	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); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

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

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