1-(4-Meth-oxy-phen-yl)pyrrolidine-2,5-dione.

In the title compound, C11H11NO3, the di-hydro-furan-2,5-dione ring has a shallow envelope conformation, with one of the methyl-ene C atoms displaced by 0.216 (1) Å from the other atoms. These near-planar atoms subtend a dihedral angle of 55.88 (8)° with the benzene ring. In the crystal, C-H⋯O hydrogen bonds link the mol-ecules into [010] chains.

Related literature

For related structures, see: Sirajuddin et al. (2012 ▶); Tahir et al. (2012 ▶).

Experimental

Crystal data

C11H11NO3

M = 205.21

Monoclinic,

a = 9.3684 (7) Å

b = 6.6146 (4) Å

c = 16.0720 (11) Å

β = 99.939 (4)°

V = 981.01 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.32 × 0.25 × 0.22 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.968, T max = 0.978

7585 measured reflections

1927 independent reflections

1626 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.094

S = 1.04

1927 reflections

138 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.14 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813022460/hb7117sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813022460/hb7117Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813022460/hb7117Isup3.cml

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

C11H11NO3	Z = 4
Mr = 205.21	F(000) = 432
Monoclinic, P21/n	Dx = 1.389 Mg m−3
a = 9.3684 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 6.6146 (4) Å	µ = 0.10 mm−1
c = 16.0720 (11) Å	T = 296 K
β = 99.939 (4)°	Prism, colourless
V = 981.01 (12) Å3	0.32 × 0.25 × 0.22 mm

Bruker Kappa APEXII CCD diffractometer	1927 independent reflections
Radiation source: fine-focus sealed tube	1626 reflections with I > 2σ(I)
Detector resolution: 8 pixels mm-1	Rint = 0.018
ω scans	θmax = 26.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −11→11
Tmin = 0.968, Tmax = 0.978	k = −8→7
7585 measured reflections	l = −19→19

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.034	w = 1/[σ2(Fo2) + (0.0409P)2 + 0.2498P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.094	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.14 e Å−3
1927 reflections	Δρmin = −0.14 e Å−3
138 parameters	Extinction correction: SHELXL2012 (Sheldrick, 2012), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.047 (4)

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.

	x	y	z	Uiso*/Ueq
O1	0.73798 (12)	−0.12759 (16)	0.03467 (7)	0.0594 (3)
O2	0.52321 (14)	−0.03671 (17)	0.38782 (7)	0.0685 (4)
O3	0.38050 (12)	0.48906 (15)	0.21179 (6)	0.0588 (3)
N1	0.48031 (11)	0.21443 (15)	0.28804 (6)	0.0397 (3)
C1	0.54572 (13)	0.12100 (19)	0.22333 (7)	0.0378 (3)
C2	0.50543 (14)	−0.0707 (2)	0.19526 (8)	0.0418 (3)
H2	0.4367	−0.1412	0.2192	0.050*
C3	0.56658 (14)	−0.1592 (2)	0.13165 (8)	0.0441 (3)
H3	0.5385	−0.2882	0.1125	0.053*
C4	0.66963 (14)	−0.0546 (2)	0.09689 (8)	0.0427 (3)
C5	0.71239 (14)	0.1368 (2)	0.12663 (9)	0.0461 (3)
H5	0.7830	0.2061	0.1039	0.055*
C6	0.65080 (14)	0.2246 (2)	0.18962 (8)	0.0427 (3)
H6	0.6797	0.3529	0.2094	0.051*
C7	0.6833 (2)	−0.3084 (2)	−0.00666 (10)	0.0639 (4)
H7A	0.6941	−0.4177	0.0333	0.096*
H7B	0.7362	−0.3386	−0.0512	0.096*
H7C	0.5825	−0.2911	−0.0299	0.096*
C8	0.47536 (15)	0.1275 (2)	0.36638 (8)	0.0471 (3)
C9	0.39873 (18)	0.2721 (2)	0.41557 (9)	0.0556 (4)
H9A	0.4574	0.3009	0.4701	0.067*
H9B	0.3067	0.2164	0.4244	0.067*
C10	0.37563 (16)	0.4609 (2)	0.36233 (9)	0.0494 (4)
H10A	0.2764	0.5078	0.3572	0.059*
H10B	0.4402	0.5679	0.3869	0.059*
C11	0.40880 (14)	0.39934 (19)	0.27787 (8)	0.0418 (3)

	U11	U22	U33	U12	U13	U23
O1	0.0720 (7)	0.0563 (6)	0.0574 (6)	−0.0022 (5)	0.0327 (5)	−0.0108 (5)
O2	0.0974 (9)	0.0604 (7)	0.0501 (6)	0.0251 (6)	0.0192 (6)	0.0146 (5)
O3	0.0802 (7)	0.0454 (6)	0.0510 (6)	0.0083 (5)	0.0116 (5)	0.0074 (5)
N1	0.0446 (6)	0.0388 (6)	0.0366 (6)	0.0017 (4)	0.0099 (4)	−0.0006 (4)
C1	0.0399 (6)	0.0397 (6)	0.0337 (6)	0.0018 (5)	0.0065 (5)	−0.0006 (5)
C2	0.0427 (7)	0.0406 (7)	0.0440 (7)	−0.0038 (5)	0.0125 (5)	0.0014 (5)
C3	0.0488 (7)	0.0380 (7)	0.0458 (7)	−0.0034 (6)	0.0090 (6)	−0.0048 (6)
C4	0.0447 (7)	0.0458 (7)	0.0388 (7)	0.0036 (6)	0.0110 (5)	−0.0010 (6)
C5	0.0450 (7)	0.0468 (8)	0.0494 (8)	−0.0058 (6)	0.0163 (6)	0.0017 (6)
C6	0.0453 (7)	0.0392 (7)	0.0436 (7)	−0.0054 (5)	0.0079 (5)	−0.0033 (5)
C7	0.0837 (11)	0.0598 (10)	0.0514 (9)	0.0052 (8)	0.0207 (8)	−0.0129 (7)
C8	0.0540 (8)	0.0498 (8)	0.0377 (7)	0.0036 (6)	0.0088 (6)	0.0021 (6)
C9	0.0657 (9)	0.0614 (9)	0.0430 (8)	0.0048 (7)	0.0183 (7)	−0.0035 (7)
C10	0.0496 (8)	0.0492 (8)	0.0502 (8)	0.0003 (6)	0.0110 (6)	−0.0116 (6)
C11	0.0440 (7)	0.0363 (6)	0.0447 (7)	−0.0034 (5)	0.0066 (5)	−0.0023 (6)

O1—C4	1.3654 (16)	C5—C6	1.3773 (18)
O1—C7	1.4203 (18)	C5—H5	0.9300
O2—C8	1.2028 (17)	C6—H6	0.9300
O3—C11	1.2055 (16)	C7—H7A	0.9600
N1—C11	1.3905 (16)	C7—H7B	0.9600
N1—C8	1.3920 (17)	C7—H7C	0.9600
N1—C1	1.4350 (15)	C8—C9	1.5002 (19)
C1—C2	1.3766 (18)	C9—C10	1.508 (2)
C1—C6	1.3844 (18)	C9—H9A	0.9700
C2—C3	1.3850 (18)	C9—H9B	0.9700
C2—H2	0.9300	C10—C11	1.5003 (18)
C3—C4	1.3819 (18)	C10—H10A	0.9700
C3—H3	0.9300	C10—H10B	0.9700
C4—C5	1.3873 (19)
C4—O1—C7	117.61 (11)	O1—C7—H7B	109.5
C11—N1—C8	112.27 (11)	H7A—C7—H7B	109.5
C11—N1—C1	123.43 (10)	O1—C7—H7C	109.5
C8—N1—C1	124.25 (11)	H7A—C7—H7C	109.5
C2—C1—C6	120.06 (11)	H7B—C7—H7C	109.5
C2—C1—N1	120.46 (11)	O2—C8—N1	124.27 (13)
C6—C1—N1	119.47 (11)	O2—C8—C9	127.83 (13)
C1—C2—C3	120.42 (12)	N1—C8—C9	107.89 (12)
C1—C2—H2	119.8	C8—C9—C10	105.29 (11)
C3—C2—H2	119.8	C8—C9—H9A	110.7
C4—C3—C2	119.58 (12)	C10—C9—H9A	110.7
C4—C3—H3	120.2	C8—C9—H9B	110.7
C2—C3—H3	120.2	C10—C9—H9B	110.7
O1—C4—C3	124.58 (12)	H9A—C9—H9B	108.8
O1—C4—C5	115.53 (12)	C11—C10—C9	104.87 (11)
C3—C4—C5	119.87 (12)	C11—C10—H10A	110.8
C6—C5—C4	120.36 (12)	C9—C10—H10A	110.8
C6—C5—H5	119.8	C11—C10—H10B	110.8
C4—C5—H5	119.8	C9—C10—H10B	110.8
C5—C6—C1	119.69 (12)	H10A—C10—H10B	108.8
C5—C6—H6	120.2	O3—C11—N1	124.39 (12)
C1—C6—H6	120.2	O3—C11—C10	127.96 (13)
O1—C7—H7A	109.5	N1—C11—C10	107.65 (11)
C11—N1—C1—C2	−123.12 (13)	N1—C1—C6—C5	−179.05 (11)
C8—N1—C1—C2	53.95 (17)	C11—N1—C8—O2	176.06 (14)
C11—N1—C1—C6	57.37 (16)	C1—N1—C8—O2	−1.3 (2)
C8—N1—C1—C6	−125.55 (14)	C11—N1—C8—C9	−2.76 (16)
C6—C1—C2—C3	−1.76 (19)	C1—N1—C8—C9	179.88 (12)
N1—C1—C2—C3	178.74 (11)	O2—C8—C9—C10	174.72 (15)
C1—C2—C3—C4	0.6 (2)	N1—C8—C9—C10	−6.52 (16)
C7—O1—C4—C3	10.8 (2)	C8—C9—C10—C11	12.49 (15)
C7—O1—C4—C5	−170.72 (13)	C8—N1—C11—O3	−168.93 (13)
C2—C3—C4—O1	179.31 (12)	C1—N1—C11—O3	8.5 (2)
C2—C3—C4—C5	0.8 (2)	C8—N1—C11—C10	11.02 (15)
O1—C4—C5—C6	−179.76 (12)	C1—N1—C11—C10	−171.59 (11)
C3—C4—C5—C6	−1.2 (2)	C9—C10—C11—O3	165.50 (14)
C4—C5—C6—C1	0.0 (2)	C9—C10—C11—N1	−14.44 (14)
C2—C1—C6—C5	1.44 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O3i	0.93	2.50	3.1666 (17)	129
C5—H5···O2ii	0.93	2.47	3.3245 (17)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O3i	0.93	2.50	3.1666 (17)	129
C5—H5⋯O2ii	0.93	2.47	3.3245 (17)	152

Symmetry codes: (i) ; (ii) .