1-(4-Meth­oxy­phen­yl)pyrrolidine-2,5-dione

Sirajuddin, M.; Ali, S.

doi:10.1107/S1600536813022460

organic compounds

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ISSN: 2056-9890

Volume 69| Part 9| September 2013| Page o1439

doi:10.1107/S1600536813022460

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1-(4-Methoxyphenyl)pyrrolidine-2,5-dione

Muhammad Sirajuddin ^a ^* and Saqib Ali ^a

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad, Pakistan
^*Correspondence e-mail: m.siraj09@yahoo.com

(Received 5 August 2013; accepted 9 August 2013; online 17 August 2013)

In the title compound, C₁₁H₁₁NO₃, the dihydrofuran-2,5-dione ring has a shallow envelope conformation, with one of the methylene 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 molecules into [010] chains.

Related literature

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

Experimental

Crystal data

C₁₁H₁₁NO₃
M_r = 205.21
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.034
wR(F²) = 0.094
S = 1.04
1927 reflections
138 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.14 e Å⁻³

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) x, y-1, z; (ii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813022460/hb7117sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536813022460/hb7117Isup3.cml

checkCIF report

Related literature top

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

Experimental top

Equimolar quantities of 4-methoxyaniline and dihydrofuran-2,5-dione were stirred and refluxed in acetic acid for 4 h. The solution was kept at room temperature for 24 h which afforded colourless prisms of the title compound.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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 (Spek, 2009).

Figures top

	Fig. 1. View of the title compound with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. The partial packing, which shows that molecules form dimers due to C—H···O bondings.

1-(4-Methoxyphenyl)pyrrolidine-2,5-dione top

Crystal data top

C₁₁H₁₁NO₃	Z = 4
M_r = 205.21	F(000) = 432
Monoclinic, P2₁/n	D_x = 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

Data collection top

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	R_int = 0.018
ω scans	θ_max = 26.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −11→11
T_min = 0.968, T_max = 0.978	k = −8→7
7585 measured reflections	l = −19→19

Refinement top

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(F_o²) + (0.0409P)² + 0.2498P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.094	(Δ/σ)_max < 0.001
S = 1.04	Δρ_max = 0.14 e Å⁻³
1927 reflections	Δρ_min = −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)

Crystal data top

C₁₁H₁₁NO₃	V = 981.01 (12) Å³
M_r = 205.21	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.3684 (7) Å	µ = 0.10 mm⁻¹
b = 6.6146 (4) Å	T = 296 K
c = 16.0720 (11) Å	0.32 × 0.25 × 0.22 mm
β = 99.939 (4)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	1927 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1626 reflections with I > 2σ(I)
T_min = 0.968, T_max = 0.978	R_int = 0.018
7585 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.094	H-atom parameters constrained
S = 1.04	Δρ_max = 0.14 e Å⁻³
1927 reflections	Δρ_min = −0.14 e Å⁻³
138 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.

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

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, y−1, z; (ii) −x+3/2, y+1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

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) x, y−1, z; (ii) −x+3/2, y+1/2, −z+1/2.

Acknowledgements

The authors acknowledge Quaid-i-Azam University, Islamabad, Pakistan, for providing research facilities, and the University Research Fund (URF) for financial support.

References

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