1-[2-(3-Meth-oxy-phen-yl)eth-yl]pyrroli-dine-2,5-dione.

In the title compound, C13H15NO3, the pyrrolidine ring makes a dihedral angle of 4.69 (9)° with the 3-meth-oxy-phenyl ring. In the crystal, hydrogen-bonded chains running along [101] are generated by connecting neighbouring mol-ecules 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 = 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

Δρmax = 0.12 e Å−3

Δρmin = −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 ▶).

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

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

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813023751/su2640Isup3.cml

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

C13H15NO3	F(000) = 496
Mr = 233.26	Dx = 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

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

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(Fo2) + (0.0544P)2 + 0.1677P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
2615 reflections	Δρmax = 0.12 e Å−3
156 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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) ; (ii) ; (iii) .