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

Fatima, Z.; Selvakumar, J.; Srinivasan, T.; Velmurugan, D.

doi:10.1107/S1600536813023751

organic compounds

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ISSN: 2056-9890

Volume 69| Part 9| September 2013| Page o1489

doi:10.1107/S1600536813023751

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

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

^aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and ^bDepartment of Chemistry, Pondicherry University, Puducherry 605 014, India
^*Correspondence e-mail: shirai2011@gmail.com

(Received 19 August 2013; accepted 22 August 2013; online 31 August 2013)

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, C c
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[F² > 2σ(F²)] = 0.035
wR(F²) = 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

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
Symmetry codes: (i) $[x+{\script{1\over 2}}, y+{\script{1\over 2}}, z+1]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[x, -y+1, z-{\script{1\over 2}}]$ .

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813023751/su2640sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536813023751/su2640Isup3.cml

checkCIF report

Comment top

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).

Related literature top

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 top

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.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title molecule, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The crystal packing of the title compound viewed along the c axis. Hydrogen bonds are shown as dashed lines (see Table 1 for details; H atoms not involved in hydrogen bonding have been omitted for clarity).

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

Crystal data top

C₁₃H₁₅NO₃	F(000) = 496
M_r = 233.26	D_x = 1.283 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 2615 reflections
a = 12.8719 (9) Å	θ = 2.3–28.4°
b = 12.5878 (8) Å	µ = 0.09 mm⁻¹
c = 7.4523 (5) Å	T = 293 K
β = 90.831 (3)°	Block, colourless
V = 1207.36 (14) Å³	0.40 × 0.35 × 0.20 mm
Z = 4

Data collection top

Bruker SMART APEXII area-detector diffractometer	2615 independent reflections
Radiation source: fine-focus sealed tube	2328 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ω and ϕ scans	θ_max = 28.4°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −17→17
T_min = 0.964, T_max = 0.982	k = −15→16
5692 measured reflections	l = −9→9

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.035	H-atom parameters constrained
wR(F²) = 0.097	w = 1/[σ²(F_o²) + (0.0544P)² + 0.1677P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
2615 reflections	Δρ_max = 0.12 e Å⁻³
156 parameters	Δρ_min = −0.16 e Å⁻³
2 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0149 (15)

Crystal data top

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

Data collection top

Bruker SMART APEXII area-detector diffractometer	2615 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	2328 reflections with I > 2σ(I)
T_min = 0.964, T_max = 0.982	R_int = 0.024
5692 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	2 restraints
wR(F²) = 0.097	H-atom parameters constrained
S = 1.02	Δρ_max = 0.12 e Å⁻³
2615 reflections	Δρ_min = −0.16 e Å⁻³
156 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.95763 (19)	0.43725 (18)	1.0655 (3)	0.0832 (6)
H1A	0.9806	0.4494	0.9452	0.125*
H1B	1.0043	0.4716	1.1487	0.125*
H1C	0.8890	0.4657	1.0789	0.125*
C2	0.90109 (11)	0.26275 (13)	0.9852 (2)	0.0485 (3)
C3	0.91325 (14)	0.15484 (15)	1.0131 (2)	0.0633 (4)
H3	0.9582	0.1300	1.1025	0.076*
C4	0.85800 (17)	0.08476 (14)	0.9071 (3)	0.0695 (5)
H4	0.8652	0.0121	0.9261	0.083*
C5	0.79213 (14)	0.12096 (13)	0.7730 (2)	0.0609 (4)
H5	0.7552	0.0726	0.7026	0.073*
C6	0.78069 (11)	0.22844 (13)	0.74273 (18)	0.0472 (3)
C7	0.83541 (11)	0.29992 (12)	0.85029 (19)	0.0450 (3)
H7	0.8280	0.3726	0.8317	0.054*
C8	0.70939 (12)	0.26805 (15)	0.5942 (2)	0.0564 (4)
H8A	0.6893	0.3408	0.6193	0.068*
H8B	0.6468	0.2251	0.5907	0.068*
C9	0.76102 (13)	0.26346 (15)	0.4132 (2)	0.0565 (4)
H9A	0.8161	0.3159	0.4094	0.068*
H9B	0.7920	0.1939	0.3972	0.068*
C10	0.63151 (13)	0.20320 (14)	0.1850 (2)	0.0573 (4)
C11	0.56115 (15)	0.25110 (19)	0.0462 (3)	0.0737 (6)
H11A	0.4891	0.2352	0.0712	0.088*
H11B	0.5774	0.2247	−0.0724	0.088*
C12	0.58151 (16)	0.36961 (19)	0.0592 (3)	0.0777 (6)
H12A	0.6066	0.3969	−0.0540	0.093*
H12B	0.5185	0.4073	0.0896	0.093*
C13	0.66250 (15)	0.38270 (13)	0.2046 (2)	0.0609 (4)
N1	0.68700 (9)	0.28356 (10)	0.26754 (15)	0.0475 (3)
O1	0.95629 (10)	0.32628 (11)	1.10049 (17)	0.0690 (3)
O2	0.70187 (17)	0.46337 (11)	0.2584 (2)	0.0967 (5)
O3	0.64082 (15)	0.11124 (11)	0.2245 (2)	0.0906 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0866 (14)	0.0787 (13)	0.0843 (14)	−0.0200 (11)	−0.0031 (11)	−0.0264 (11)
C2	0.0412 (7)	0.0623 (8)	0.0421 (7)	0.0004 (7)	0.0000 (6)	−0.0038 (7)
C3	0.0629 (10)	0.0683 (10)	0.0585 (10)	0.0098 (8)	−0.0075 (8)	0.0138 (8)
C4	0.0825 (12)	0.0484 (9)	0.0773 (12)	0.0001 (8)	−0.0032 (10)	0.0119 (8)
C5	0.0636 (10)	0.0534 (9)	0.0658 (11)	−0.0099 (7)	−0.0003 (8)	−0.0074 (7)
C6	0.0405 (7)	0.0586 (8)	0.0425 (7)	−0.0008 (6)	0.0019 (6)	−0.0018 (6)
C7	0.0429 (7)	0.0486 (7)	0.0437 (7)	0.0016 (6)	0.0014 (6)	−0.0002 (6)
C8	0.0444 (7)	0.0769 (10)	0.0478 (8)	0.0049 (7)	−0.0064 (6)	−0.0044 (8)
C9	0.0434 (7)	0.0776 (11)	0.0483 (8)	0.0044 (7)	−0.0084 (6)	0.0034 (8)
C10	0.0570 (9)	0.0649 (11)	0.0502 (8)	−0.0133 (7)	0.0058 (7)	−0.0053 (7)
C11	0.0508 (9)	0.1229 (19)	0.0473 (8)	−0.0130 (10)	−0.0052 (7)	0.0007 (10)
C12	0.0687 (12)	0.1047 (16)	0.0596 (10)	0.0264 (11)	0.0000 (9)	0.0204 (10)
C13	0.0717 (11)	0.0584 (9)	0.0529 (10)	0.0049 (8)	0.0093 (8)	0.0062 (7)
N1	0.0448 (6)	0.0538 (7)	0.0439 (7)	−0.0009 (5)	−0.0041 (5)	−0.0004 (5)
O1	0.0654 (7)	0.0838 (9)	0.0573 (7)	−0.0055 (6)	−0.0185 (5)	−0.0104 (6)
O2	0.1454 (15)	0.0532 (7)	0.0917 (10)	−0.0170 (9)	0.0081 (10)	−0.0025 (7)
O3	0.1184 (13)	0.0569 (8)	0.0962 (12)	−0.0184 (7)	−0.0033 (10)	−0.0054 (7)

Geometric parameters (Å, º) top

C1—O1	1.421 (3)	C8—H8A	0.9700
C1—H1A	0.9600	C8—H8B	0.9700
C1—H1B	0.9600	C9—N1	1.4562 (19)
C1—H1C	0.9600	C9—H9A	0.9700
C2—O1	1.3654 (19)	C9—H9B	0.9700
C2—C3	1.383 (2)	C10—O3	1.200 (2)
C2—C7	1.386 (2)	C10—N1	1.378 (2)
C3—C4	1.376 (3)	C10—C11	1.492 (3)
C3—H3	0.9300	C11—C12	1.517 (3)
C4—C5	1.379 (3)	C11—H11A	0.9700
C4—H4	0.9300	C11—H11B	0.9700
C5—C6	1.379 (2)	C12—C13	1.502 (3)
C5—H5	0.9300	C12—H12A	0.9700
C6—C7	1.390 (2)	C12—H12B	0.9700
C6—C8	1.512 (2)	C13—O2	1.201 (2)
C7—H7	0.9300	C13—N1	1.368 (2)
C8—C9	1.513 (2)

O1—C1—H1A	109.5	H8A—C8—H8B	107.9
O1—C1—H1B	109.5	N1—C9—C8	111.51 (13)
H1A—C1—H1B	109.5	N1—C9—H9A	109.3
O1—C1—H1C	109.5	C8—C9—H9A	109.3
H1A—C1—H1C	109.5	N1—C9—H9B	109.3
H1B—C1—H1C	109.5	C8—C9—H9B	109.3
O1—C2—C3	115.10 (14)	H9A—C9—H9B	108.0
O1—C2—C7	124.41 (14)	O3—C10—N1	123.31 (18)
C3—C2—C7	120.48 (14)	O3—C10—C11	128.13 (18)
C4—C3—C2	119.16 (15)	N1—C10—C11	108.56 (15)
C4—C3—H3	120.4	C10—C11—C12	104.51 (15)
C2—C3—H3	120.4	C10—C11—H11A	110.8
C3—C4—C5	120.78 (16)	C12—C11—H11A	110.9
C3—C4—H4	119.6	C10—C11—H11B	110.8
C5—C4—H4	119.6	C12—C11—H11B	110.9
C4—C5—C6	120.39 (16)	H11A—C11—H11B	108.9
C4—C5—H5	119.8	C13—C12—C11	105.73 (15)
C6—C5—H5	119.8	C13—C12—H12A	110.6
C5—C6—C7	119.25 (14)	C11—C12—H12A	110.6
C5—C6—C8	120.36 (14)	C13—C12—H12B	110.6
C7—C6—C8	120.39 (15)	C11—C12—H12B	110.6
C2—C7—C6	119.91 (14)	H12A—C12—H12B	108.7
C2—C7—H7	120.0	O2—C13—N1	124.25 (18)
C6—C7—H7	120.0	O2—C13—C12	128.20 (19)
C6—C8—C9	111.72 (12)	N1—C13—C12	107.54 (16)
C6—C8—H8A	109.3	C13—N1—C10	113.65 (14)
C9—C8—H8A	109.3	C13—N1—C9	123.99 (15)
C6—C8—H8B	109.3	C10—N1—C9	122.31 (15)
C9—C8—H8B	109.3	C2—O1—C1	117.90 (14)

O1—C2—C3—C4	177.92 (17)	C10—C11—C12—C13	0.1 (2)
C7—C2—C3—C4	−1.1 (3)	C11—C12—C13—O2	179.5 (2)
C2—C3—C4—C5	0.8 (3)	C11—C12—C13—N1	0.5 (2)
C3—C4—C5—C6	0.1 (3)	O2—C13—N1—C10	−179.95 (18)
C4—C5—C6—C7	−0.7 (3)	C12—C13—N1—C10	−0.94 (19)
C4—C5—C6—C8	179.27 (16)	O2—C13—N1—C9	2.7 (3)
O1—C2—C7—C6	−178.43 (15)	C12—C13—N1—C9	−178.33 (15)
C3—C2—C7—C6	0.4 (2)	O3—C10—N1—C13	−178.52 (19)
C5—C6—C7—C2	0.5 (2)	C11—C10—N1—C13	1.00 (19)
C8—C6—C7—C2	−179.55 (14)	O3—C10—N1—C9	−1.1 (2)
C5—C6—C8—C9	−80.96 (19)	C11—C10—N1—C9	178.43 (16)
C7—C6—C8—C9	99.05 (18)	C8—C9—N1—C13	87.3 (2)
C6—C8—C9—N1	169.92 (15)	C8—C9—N1—C10	−89.88 (19)
O3—C10—C11—C12	178.89 (19)	C3—C2—O1—C1	172.27 (18)
N1—C10—C11—C12	−0.6 (2)	C7—C2—O1—C1	−8.8 (2)

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) x+1/2, y+1/2, z+1; (ii) x−1/2, −y+1/2, z−1/2; (iii) x, −y+1, z−1/2.

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) x+1/2, y+1/2, z+1; (ii) x−1/2, −y+1/2, z−1/2; (iii) x, −y+1, z−1/2.

Acknowledgements

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.

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