1-[2-(3-Meth­oxy­phen­yl)eth­yl]pyrroli­dine-2,5-dione

Zeenat Fatima; Jayaraman Selvakumar; Thothadri Srinivasan; Devadasan Velmurugan

doi:10.1107/S1600536813023751

. 2013 Aug 31;69(Pt 9):o1489. doi: 10.1107/S1600536813023751

1-[2-(3-Methoxyphenyl)ethyl]pyrrolidine-2,5-dione

Zeenat Fatima ^a, Jayaraman Selvakumar ^b, Thothadri Srinivasan ^a, Devadasan Velmurugan ^a,^*

PMCID: PMC3884377 PMID: 24427107

Abstract

In the title compound, C₁₃H₁₅NO₃, the pyrrolidine ring makes a dihedral angle of 4.69 (9)° with the 3-methoxy-phenyl ring. In the crystal, hydrogen-bonded chains running along [101] are generated by connecting neighbouring molecules via C—H⋯O hydrogen bonds. Parallel chains are linked by further C—H⋯O hydrogen bonds, forming a three-dimensional structure.

Related literature

For the bioactivity of pyrrolidine-2,5-dione derivatives, see: Obniska et al. (2012 ▶); Ha et al. (2011 ▶); Kaminski et al. (2011 ▶). For related structures, see: Khorasani & Fernandes (2012 ▶); Mayes et al. (2008 ▶).

Experimental

Crystal data

C₁₃H₁₅NO₃
M _r = 233.26
Monoclinic,
a = 12.8719 (9) Å
b = 12.5878 (8) Å
c = 7.4523 (5) Å
β = 90.831 (3)°
V = 1207.36 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.40 × 0.35 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T _min = 0.964, T _max = 0.982
5692 measured reflections
2615 independent reflections
2328 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.097
S = 1.02
2615 reflections
156 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813023751/su2640sup1.cif

e-69-o1489-sup1.cif^{(22.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813023751/su2640Isup2.hkl

e-69-o1489-Isup2.hkl^{(125.8KB, hkl)}

Click here for additional data file.^{(4.8KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813023751/su2640Isup3.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
C1—H1B⋯O3ⁱ	0.96	2.54	3.418 (3)	151
C8—H8B⋯O1ⁱⁱ	0.97	2.54	3.469 (2)	161
C12—H12A⋯O2ⁱⁱⁱ	0.97	2.57	3.456 (3)	152

Open in a new tab

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

Acknowledgments

We are grateful to Dr C. R. Ramanathan, Department of Chemistry, Pondicherry University for support of this research. The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection. ZF and DV acknowledge the UGC (SAP–CAS) for departmental facilities. ZF also thanks the UGC for a meritorious fellowship.

supplementary crystallographic information

1. Comment

Pyrrolidine-2,5-dione derivates are an important class of heterocylic compounds with essential applications in medicinal chemistry and organic synthesis. They exhibit numerous bioactivities, for example anticonvulsant (Obniska et al., 2012; Kaminski et al., 2011) and tyrosinase inhibitory activity (Ha et al., 2011). In the field of organic chemistry derivates, like 1-bromopyrrolidine-2,5-dione (NBS), are the most commonly used halogenation reagents. In view of the different applications of this class of compounds, we have synthesized the title derivative and report herein on its crystal structure.

In the title compound, Fig. 1, the pyrrolidine ring (N1/C10—C13) makes a dihedral angle of 4.69 (9)° with the benzene ring (C2—C7).

In the crystal, hydrogen-bonded chains running along [101] are generated by connecting neighbouring molecules via C—H···O hydrogen bonds (Table 1 and Fig. 2). Parallel chains are linked by further C—H···O hydrogen bonds forming a three-dimensional structure (Table 1 and Fig. 2).

2. Experimental

3-methoxy phenethylamine (1.51 g, 10 mmol) and succinic anhydride (1.2 g, 12 mmol) were stirred at room temperature in dry ethyl acetate for 30 min. Ethyl acetate was removed under reduced pressure, and the resulting residue was dissolved in toluene. Acetyl chloride (5 equiv) was then added and the mixture refluxed for 1 h. The reaction mixture was washed with aqueous Na₂CO₃ and dried over anhydrous Na₂SO₄, filtered and concentrated under reduced pressure followed by silica gel column purification using hexane ethyl acetate (30:70) as eluent to afford the title compound as a colourless solid. Single crystals suitable for X-ray diffraction analysis were obtained by slow evaporation of a solution of the title compound in ethanol at room temperature.