2,2-Diethyl 4-methyl 5-(4-nitro­phen­yl)-4-phenyl­pyrrolidine-2,2,4-tricarboxyl­ate

Long He

doi:10.1107/S1600536811036038

. 2011 Sep 14;67(Pt 10):o2593. doi: 10.1107/S1600536811036038

2,2-Diethyl 4-methyl 5-(4-nitrophenyl)-4-phenylpyrrolidine-2,2,4-tricarboxylate

Long He ^a,^*

PMCID: PMC3201539 PMID: 22065547

Abstract

The title compound, C₂₄H₂₆N₂O₈, was synthesized by the cycloaddition reaction of methyl 2-phenylacrylate, diethyl 2-aminomalonate and 4-nitrobenzaldehyde. The pyrrolidine ring exhibits an envelope conformation. The two benzene rings are located on opposite sides of the pyrrolidine ring and subtend a dihedral angle of 59.16 (14)°. The crystal packing is stabilized by N—H⋯O and weak C—H⋯O hydrogen bonding.

Related literature

For the biological activity of pyrrolidine derivatives, see: Coldham & Hufton (2005 ▶); Nair & Suja (2007 ▶); Pandey et al. (2006 ▶); Sardina & Rapoport (1996 ▶). For a related structure, see: Yu et al. (2007 ▶).

Experimental

Crystal data

C₂₄H₂₆N₂O₈
M _r = 470.47
Orthorhombic,
a = 9.7948 (1) Å
b = 10.9356 (2) Å
c = 22.3240 (3) Å
V = 2391.17 (6) Å³
Z = 4
Cu Kα radiation
μ = 0.83 mm⁻¹
T = 120 K
0.44 × 0.40 × 0.36 mm

Data collection

Gemini S Ultra, Oxford Diffraction diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T _min = 0.712, T _max = 0.755
21308 measured reflections
4686 independent reflections
4613 reflections with I > 2σ(I)
R _int = 0.018

Refinement

R[F ² > 2σ(F ²)] = 0.025
wR(F ²) = 0.068
S = 1.02
4686 reflections
314 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.19 e Å⁻³
Absolute structure: Flack (1983 ▶), 1995 Friedel pairs
Flack parameter: 0.05 (10)

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811036038/xu5319sup1.cif

e-67-o2593-sup1.cif^{(23.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811036038/xu5319Isup2.hkl

e-67-o2593-Isup2.hkl^{(224.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811036038/xu5319Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1⋯O7ⁱ	0.88 (1)	2.59 (1)	3.360 (4)	148 (1)
C12—H12C⋯O1ⁱⁱ	0.96	2.58	3.360 (2)	139 (1)

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

Acknowledgments

The diffraction data were collected at the Centre for Testing and Analysis, Chengdu Branch, Chinese Academy of Sciences. The author acknowledges financial support from China West Normal University.

supplementary crystallographic information

Comment

Substituted pyrrolidine compound is an important class of heterocyclic compounds with wide spread applications to the synthesis of biologically active compounds and natural products (Coldham & Hufton, 2005; Nair & Suja, 2007; Pandey et al., 2006; Sardina & Rapoport, 1996). Its crystal structure is reported here.

The molecular structure of (I) is shown in (Table 2). Bond lengths and angles in (I) are normal. The pyrrolidine ring possesses an envelope conformation. The dihedral angle between the C1—C6 and C13—C18 benzene planes is 59.16 (14)°. The crystal packing is stabilized by N—H···O and C—H···O hydrogen bonds (Table 1).

Experimental

Diethyl 2-aminomalonate (0.0175 g, 0.1 mmol) were added to a solution of 4-nitrobenzaldehyde (0.018 g, 0.12 mmol) and methyl 2-phenylacrylate (0.08 g, 0.5 mmol) in dichloromethane (1 ml). To the stirred mixture, acetic acid (0.003 g, 0.05 mmol) was added. After the mixture had been stirred at 298 K for 24 h, the reaction was quenched with a saturated solution of sodium bicarbonate (5 ml). The mixture was extracted with diethyl ether, evaporated and separated by flash chromatograghy. A colourless powder was obtained. Single crystals suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution.