Crystal structure of 1,3-dimethyl-3-phenyl-pyrrolidine-2,5-dione: a clinically used anti-convulsant.

In the title compound, C12H13NO2, the five-membered ring has an envelope conformation; the disubstituted C atom lies out of the mean plane through the four other ring atoms (r.m.s. deviation = 0.0038 Å) by 0.1877 (18) Å. The plane of the phenyl substituent is practically perpendicular to that of the planar part of the five-membered ring, with a dihedral angle of 87.01 (5)°. In the crystal, mol-ecules are linked by weak C-H⋯O hydrogen bonds, forming inversion dimers. The dimers are linked by further C-H⋯O hydrogen bonds, as well as carbon-yl-carbonyl attractive inter-actions [O⋯C = 3.2879 (19) Å], forming a three-dimensional framework structure.

Related literature

For general background to the properties of α-substituted cyclic imides, see: Chen et al. (1951 ▶, 2014 ▶); Vida & Gerry (1977 ▶); Kuhnert-Brandstätter & Bösch (1978 ▶); Sigler et al. (2001 ▶); Lin et al. (2012 ▶). For the crystal structures of some succinimide derivatives, see: Argay & Carstensen-Oeser (1973 ▶); Argay & Kálmán (1973 ▶); Argay & Seres (1973 ▶); Kwiatkowski & Karolak-Wojciechowska (1992 ▶); Khrustalev et al. (2014 ▶). For carbon­yl–carbonyl inter­actions, see: Allen et al. (1998 ▶).

Experimental

Crystal data

C12H13NO2

M = 203.23

Monoclinic,

a = 10.517 (5) Å

b = 7.383 (3) Å

c = 13.568 (6) Å

β = 102.332 (6)°

V = 1029.2 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.45 × 0.35 × 0.25 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.961, T max = 0.978

11948 measured reflections

3170 independent reflections

2401 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.117

S = 1.04

3170 reflections

138 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.20 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: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814016717/su2755sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814016717/su2755Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814016717/su2755Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814016717/su2755fig1.tif

Mol­ecular structure of the title mol­ecule, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

Click here for additional data file.

. DOI: 10.1107/S1600536814016717/su2755fig2.tif

A view along the b axis of the crystal packing of the title compound. The C–H⋯O hydrogen bonds (see Table 1 for details) and attractive C=O⋯C=O inter­actions are shown as dashed lines.

CCDC reference: 1015037

Additional supporting information: crystallographic information; 3D view; checkCIF report

C12H13NO2	F(000) = 432
Mr = 203.23	Dx = 1.312 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2487 reflections
a = 10.517 (5) Å	θ = 4.3–30.4°
b = 7.383 (3) Å	µ = 0.09 mm−1
c = 13.568 (6) Å	T = 100 K
β = 102.332 (6)°	Prism, colourless
V = 1029.2 (8) Å3	0.45 × 0.35 × 0.25 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	3170 independent reflections
Radiation source: fine-focus sealed tube	2401 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
φ and ω scans	θmax = 30.7°, θmin = 4.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −14→15
Tmin = 0.961, Tmax = 0.978	k = −10→10
11948 measured reflections	l = −19→19

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.051P)2 + 0.2557P] where P = (Fo2 + 2Fc2)/3
3170 reflections	(Δ/σ)max < 0.001
138 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
O1	0.22108 (8)	0.49025 (12)	0.54547 (6)	0.0254 (2)
O2	0.05261 (9)	−0.03777 (14)	0.63342 (7)	0.0329 (2)
N1	0.12281 (9)	0.24733 (15)	0.60341 (7)	0.0230 (2)
C2	0.21177 (11)	0.32854 (16)	0.55604 (8)	0.0197 (2)
C3	0.29566 (11)	0.18081 (15)	0.52209 (8)	0.0178 (2)
C4	0.22286 (11)	0.00564 (16)	0.53825 (9)	0.0213 (2)
H4A	0.1797	−0.0476	0.4726	0.026*
H4B	0.2840	−0.0846	0.5761	0.026*
C5	0.12347 (11)	0.06034 (18)	0.59769 (8)	0.0232 (2)
C6	0.03228 (12)	0.3509 (2)	0.64901 (10)	0.0320 (3)
H6A	0.0782	0.4530	0.6870	0.048*
H6B	−0.0035	0.2726	0.6948	0.048*
H6C	−0.0387	0.3967	0.5960	0.048*
C7	0.43011 (10)	0.19242 (14)	0.59288 (8)	0.0165 (2)
C8	0.53672 (11)	0.26871 (15)	0.56295 (9)	0.0207 (2)
H8	0.5273	0.3141	0.4963	0.025*
C9	0.65706 (11)	0.27933 (16)	0.62961 (10)	0.0236 (3)
H9	0.7288	0.3323	0.6081	0.028*
C10	0.67313 (12)	0.21356 (16)	0.72690 (10)	0.0233 (2)
H10	0.7558	0.2194	0.7718	0.028*
C11	0.56728 (11)	0.13896 (16)	0.75822 (9)	0.0214 (2)
H11	0.5772	0.0940	0.8250	0.026*
C12	0.44715 (11)	0.12992 (15)	0.69216 (8)	0.0186 (2)
H12	0.3750	0.0803	0.7147	0.022*
C13	0.29842 (13)	0.21253 (17)	0.41107 (9)	0.0240 (3)
H13A	0.3302	0.3352	0.4027	0.036*
H13B	0.2104	0.1988	0.3697	0.036*
H13C	0.3564	0.1239	0.3897	0.036*

	U11	U22	U33	U12	U13	U23
O1	0.0279 (5)	0.0234 (4)	0.0231 (4)	0.0064 (3)	0.0012 (3)	−0.0014 (3)
O2	0.0212 (4)	0.0458 (6)	0.0329 (5)	−0.0032 (4)	0.0084 (4)	0.0098 (4)
N1	0.0173 (5)	0.0324 (6)	0.0196 (5)	0.0046 (4)	0.0046 (4)	0.0000 (4)
C2	0.0172 (5)	0.0258 (6)	0.0147 (5)	0.0035 (4)	0.0002 (4)	0.0000 (4)
C3	0.0188 (5)	0.0192 (5)	0.0159 (5)	0.0011 (4)	0.0047 (4)	0.0008 (4)
C4	0.0189 (5)	0.0236 (6)	0.0214 (5)	−0.0023 (4)	0.0041 (4)	−0.0010 (4)
C5	0.0160 (5)	0.0340 (6)	0.0186 (5)	−0.0003 (4)	0.0016 (4)	0.0034 (5)
C6	0.0210 (6)	0.0474 (8)	0.0292 (6)	0.0099 (5)	0.0086 (5)	−0.0032 (6)
C7	0.0173 (5)	0.0153 (5)	0.0179 (5)	0.0017 (4)	0.0058 (4)	−0.0001 (4)
C8	0.0221 (6)	0.0193 (5)	0.0232 (5)	0.0014 (4)	0.0102 (4)	0.0031 (4)
C9	0.0186 (5)	0.0186 (5)	0.0358 (7)	−0.0012 (4)	0.0113 (5)	−0.0025 (5)
C10	0.0193 (5)	0.0196 (5)	0.0295 (6)	0.0026 (4)	0.0023 (4)	−0.0066 (4)
C11	0.0232 (6)	0.0215 (5)	0.0189 (5)	0.0034 (4)	0.0033 (4)	−0.0015 (4)
C12	0.0190 (5)	0.0183 (5)	0.0195 (5)	−0.0002 (4)	0.0061 (4)	0.0000 (4)
C13	0.0316 (6)	0.0249 (6)	0.0158 (5)	0.0015 (5)	0.0061 (5)	0.0000 (4)

O1—C2	1.2089 (15)	C7—C8	1.3907 (16)
O2—C5	1.2122 (15)	C7—C12	1.3987 (16)
N1—C2	1.3802 (15)	C8—C9	1.3918 (18)
N1—C5	1.3828 (18)	C8—H8	0.9500
N1—C6	1.4580 (16)	C9—C10	1.3826 (19)
C2—C3	1.5342 (16)	C9—H9	0.9500
C3—C13	1.5308 (17)	C10—C11	1.3876 (17)
C3—C7	1.5328 (16)	C10—H10	0.9500
C3—C4	1.5422 (16)	C11—C12	1.3859 (16)
C4—C5	1.5055 (17)	C11—H11	0.9500
C4—H4A	0.9900	C12—H12	0.9500
C4—H4B	0.9900	C13—H13A	0.9800
C6—H6A	0.9800	C13—H13B	0.9800
C6—H6B	0.9800	C13—H13C	0.9800
C6—H6C	0.9800
C2—N1—C5	113.30 (10)	H6B—C6—H6C	109.5
C2—N1—C6	122.61 (11)	C8—C7—C12	118.00 (10)
C5—N1—C6	123.98 (11)	C8—C7—C3	122.21 (10)
O1—C2—N1	124.36 (11)	C12—C7—C3	119.76 (10)
O1—C2—C3	126.88 (11)	C7—C8—C9	120.73 (11)
N1—C2—C3	108.76 (10)	C7—C8—H8	119.6
C13—C3—C7	113.53 (9)	C9—C8—H8	119.6
C13—C3—C2	108.64 (9)	C10—C9—C8	120.63 (11)
C7—C3—C2	106.55 (9)	C10—C9—H9	119.7
C13—C3—C4	112.49 (9)	C8—C9—H9	119.7
C7—C3—C4	112.17 (9)	C9—C10—C11	119.29 (11)
C2—C3—C4	102.63 (9)	C9—C10—H10	120.4
C5—C4—C3	105.90 (10)	C11—C10—H10	120.4
C5—C4—H4A	110.6	C12—C11—C10	120.09 (11)
C3—C4—H4A	110.6	C12—C11—H11	120.0
C5—C4—H4B	110.6	C10—C11—H11	120.0
C3—C4—H4B	110.6	C11—C12—C7	121.24 (10)
H4A—C4—H4B	108.7	C11—C12—H12	119.4
O2—C5—N1	124.28 (12)	C7—C12—H12	119.4
O2—C5—C4	127.63 (12)	C3—C13—H13A	109.5
N1—C5—C4	108.07 (10)	C3—C13—H13B	109.5
N1—C6—H6A	109.5	H13A—C13—H13B	109.5
N1—C6—H6B	109.5	C3—C13—H13C	109.5
H6A—C6—H6B	109.5	H13A—C13—H13C	109.5
N1—C6—H6C	109.5	H13B—C13—H13C	109.5
H6A—C6—H6C	109.5
C5—N1—C2—O1	174.37 (10)	C3—C4—C5—O2	−173.64 (11)
C6—N1—C2—O1	−2.00 (17)	C3—C4—C5—N1	7.94 (12)
C5—N1—C2—C3	−6.64 (13)	C13—C3—C7—C8	15.33 (15)
C6—N1—C2—C3	176.99 (10)	C2—C3—C7—C8	−104.22 (12)
O1—C2—C3—C13	−50.84 (15)	C4—C3—C7—C8	144.23 (10)
N1—C2—C3—C13	130.20 (10)	C13—C3—C7—C12	−166.67 (10)
O1—C2—C3—C7	71.83 (14)	C2—C3—C7—C12	73.78 (12)
N1—C2—C3—C7	−107.13 (10)	C4—C3—C7—C12	−37.77 (13)
O1—C2—C3—C4	−170.14 (11)	C12—C7—C8—C9	1.08 (16)
N1—C2—C3—C4	10.91 (11)	C3—C7—C8—C9	179.11 (10)
C13—C3—C4—C5	−127.64 (10)	C7—C8—C9—C10	0.25 (17)
C7—C3—C4—C5	102.92 (10)	C8—C9—C10—C11	−0.98 (17)
C2—C3—C4—C5	−11.07 (11)	C9—C10—C11—C12	0.36 (17)
C2—N1—C5—O2	−179.41 (11)	C10—C11—C12—C7	1.00 (17)
C6—N1—C5—O2	−3.10 (18)	C8—C7—C12—C11	−1.70 (16)
C2—N1—C5—C4	−0.93 (13)	C3—C7—C12—C11	−179.79 (10)
C6—N1—C5—C4	175.39 (10)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6C···O1i	0.98	2.55	3.5264 (19)	178
C11—H11···O1ii	0.95	2.57	3.2744 (17)	132

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6C⋯O1i	0.98	2.55	3.5264 (19)	178
C11—H11⋯O1ii	0.95	2.57	3.2744 (17)	132

Symmetry codes: (i) ; (ii) .