(E)-3-(Oxolan-2-yl­idene)-1-phenyl­pyrrolidine-2,5-dione

Ying Shao; Yong-An Xia; Zhu-Hong Wu; Xiao-Long Liu

doi:10.1107/S1600536814007193

. 2014 Apr 5;70(Pt 5):o521. doi: 10.1107/S1600536814007193

(E)-3-(Oxolan-2-ylidene)-1-phenylpyrrolidine-2,5-dione

Ying Shao ^a,^*, Yong-An Xia ^a, Zhu-Hong Wu ^a, Xiao-Long Liu ^a

PMCID: PMC4011259 PMID: 24860335

Abstract

In the title compound, C₁₄H₁₃NO₃, the dihedral angles between the central pyrrolidine ring and the pendant tetrahydrofuran and phenyl rings are 5.34 (18) and 58.99 (17)°, respectively. The tetrahydrofuran ring is almost planar (r.m.s. deviation = 0.008 Å). In the crystal, molecules are linked by C—H⋯O interactions, generating a three-dimensional network.

Related literature

For synthetic background, see: Han et al. (2013 ▶); Sodhi et al. (2012 ▶).

Experimental

Crystal data

C₁₄H₁₃NO₃
M _r = 243.25
Monoclinic,
a = 8.144 (2) Å
b = 13.729 (4) Å
c = 11.160 (3) Å
β = 105.177 (8)°
V = 1204.2 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.30 × 0.28 × 0.25 mm

Data collection

Rigaku Mercury CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2000 ▶) T _min = 0.736, T _max = 0.977
11234 measured reflections
2201 independent reflections
1893 reflections with I > 2σ(I)
R _int = 0.035

Refinement

R[F ² > 2σ(F ²)] = 0.075
wR(F ²) = 0.161
S = 1.08
2201 reflections
164 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: CrystalClear (Rigaku, 2000 ▶); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku, 2000 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814007193/hb7212sup1.cif

e-70-0o521-sup1.cif^{(17.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814007193/hb7212Isup2.hkl

e-70-0o521-Isup2.hkl^{(108.2KB, hkl)}

Click here for additional data file.^{(2.3KB, cdx)}

Supporting information file. DOI: 10.1107/S1600536814007193/hb7212Isup3.cdx

Click here for additional data file.^{(5KB, cml)}

Supporting information file. DOI: 10.1107/S1600536814007193/hb7212Isup4.cml

CCDC reference: 994793

Additional supporting information: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O2ⁱ	0.93	2.59	3.487 (4)	161
C9—H9A⋯O1ⁱⁱ	0.97	2.50	3.403 (3)	154
C14—H14A⋯O2ⁱⁱⁱ	0.97	2.50	3.376 (4)	150
C14—H14B⋯O2^iv	0.97	2.51	3.384 (4)	149

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) .

Acknowledgments

We gratefully acknowledge the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD), the National Natural Science Foundation of China (grant No. 21302015), and the Natural Science Fundation for Colleges and Universities of Jiangsu Province (grant No. 12KJB150005) for financial support.

supplementary crystallographic information

1. Comment

The area of allylic and benzylic oxidation with tert-butyl hydroperoxide (TBHP) in the presence of Co(acac)₂ has been attracted more and more attention (Han, et al., 2013; Sodhi, et al., 2012). The title compound, C₁₄H₁₃NO₃, was synthesized by Co(acac)₂ catalyzed cross-dehydrogenative-coupling (CDC) between 1-phenyl-1H-pyrrole-2,5-dione and tetrahydrofuran in the presence of t-BuOOH as a oxidant in the air. In the molecule of the title compound (Fig. 1), the compound adopts an E conformation. All the non-H atoms of the pyrrolidine-2,5-dione and the tetrahydrofuran fragment, linked by carbon—carbon double bond, are nearly coplanar, with a maximum deviation of 0.056 (1) Å. While the dihedral angle between the benzene ring and the pyrrolidine-2,5-dione ring is 59.9 Å. In the crystal, C—H···O interactions link the molecules (Table 1).

2. Experimental

1-Phenyl-1H-pyrrole-2,5-dione(86.6 mg, 0.5 mmol), THF (0.5 ml, 7.0 mmol), cobalt(II) acetylacetonate (12.9 mg), 1,4-diazabicyclo[2.2.2]octane (70.1 mg, 0.6 mmol), TBHP (2.0 equiv, 70% aqueous solution 140 uL), 1.0 ml acetonitrile, 1.0 ml 1,4-dioxane were added to a tube under air. The reaction mixture was stirred at 60 ^oC for 4 h. Then the reaction mixture was quenched with saturated Na₂SO₃ solution_, extracted repeatedly with ethyl acetate, and dried over Na₂SO₄. It was then removal of the organic solvent in vacuum and followed by flash silica gel column chromatographic purification afforded product with petroleum/ ethyl acetate mixtures. Yield 40%. Colourless crystals were obtained by slow evaporation of ethyl acetate and CH₂Cl₂ mixed solvent.