Crystal structure of 1,3-dimethyl-3-phenyl­pyrrolidine-2,5-dione: a clinically used anti­convulsant

Ordonez, C.; Pavlovetc, I.M.; Khrustalev, V.N.

doi:10.1107/S1600536814016717

organic compounds

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ISSN: 2056-9890

Volume 70| Part 9| September 2014| Pages o942-o943

doi:10.1107/S1600536814016717

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Crystal structure of 1,3-dimethyl-3-phenylpyrrolidine-2,5-dione: a clinically used anticonvulsant

Carlos Ordonez,^a ^* Ilia M. Pavlovetc ^b and Victor N. Khrustalev ^c

^aDepartment of Chemistry & Biology, New Mexico Highlands University, 803 University Avenue, Las Vegas, NM 87701, USA, ^bDepartment of Engineering Photonics, St Petersburg National Research University of Information Technologies, Mechanics and Optics (ITMO University), 49 Kronverkskiy Avenue, St Petersburg 197101, Russian Federation, and ^cX-Ray Structural Centre, A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Street, B-334, Moscow 119991, Russian Federation
^*Correspondence e-mail: carloso14@msn.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 12 July 2014; accepted 18 July 2014; online 1 August 2014)

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, molecules 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 carbonyl–carbonyl attractive interactions [O⋯C = 3.2879 (19) Å], forming a three-dimensional framework structure.

Keywords: crystal structure; methsuximide; anticonvulsant; α-substituted cyclic imide; succinimide.

CCDC reference: 1015037

1. 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 ).

2. Experimental

2.1. Crystal data

C₁₂H₁₃NO₂
M_r = 203.23
Monoclinic, P 2₁ /c
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

2.2. 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

2.3. Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.117
S = 1.04
3170 reflections
138 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.20 e Å⁻³

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

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: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

CCDC reference: 1015037

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814016717/su2755sup1.cif

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

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

checkCIF report

Comment top

The potent antiepileptic properties of α-substituted cyclic imides have been known for over fifty years (Chen et al., 1951; Vida & Gerry, 1977). For instance, 1,3-dimethyl-3-phenylpyrrolidine-2,5-dione (methsuximide) is a broad-spectrum anticonvulsant, valuable in the treatment of medically intractable epilepsy (Sigler et al., 2001). In vivo, methsuximide is rapidly converted into its active metabolite, 3-methyl-3-phenylpyrrolidine-2,5-dione (α-methyl-α-phenylsuccinimide). Very recently we have studied the solid-state properties and crystal structures of racemic and homochiral forms of α-methyl-α-phenylsuccinimide (Khrustalev et al., 2014; Chen et al., 2014). Moreover, we have found and described the different polymorphic modifications of this compound (Khrustalev et al., 2014). In this paper we report crystal structure of 1,3-dimethyl-3-phenylpyrrolidine-2,5-dione (methsuximide, trade-mark is Celontin).

The molecule of the title compound, C₁₂H₁₃NO₂, contains the five-membered ring in a flattened envelope conformation; the C3 carbon atom is out of the mean plane passed through the other atoms of the ring (r.m.s. deviation is 0.0038) by 0.1877 (18) Å (Fig. 1). A similar conformation of the five-membered ring was also observed in other N-substituted succinimide derivatives (Argay & Seres, 1973; Kwiatkowski & Karolak-Wojciechowska, 1992). It should be noted that the five-membered ring in the N-unsubstituted succinimide derivatives adopts almost planar conformation (Argay & Kálmán, 1973; Argay & Carstensen-Oeser, 1973; Khrustalev et al., 2014). The phenyl substituent is practically perpendicular to the five-membered ring; the dihedral angle between the planar part of the five-membered ring and the phenyl plane is 87.01 (5) °.

In the crystal, the molecules are linked by weak intermolecular C–H···O hydrogen bonds (Table 1) as well as carbonyl-carbonyl C5═ O2···C5ⁱ═O2ⁱ [C5···O2ⁱ and O2···C5ⁱ distances are 3.2879 (19) Å; symmetry code: (i) - x, - y, - z+1] attractive interactions (Allen et al., 1998) into a three-dimensional framework (Fig. 2).

It is important to point out that atom O2 does not form any intermolecular C–H···O hydrogen bonds due to the above-mentioned carbonyl-carbonyl interactions. Interestingly, molecular docking indicates that methsuximide seems to be incapable of forming hydrogen bonds with its protein target(s), which may explain why methsuximide, unlike 3-methyl-3-phenylpyrrolidine-2,5-dione, does not inhibit the nicotinic acetylcholine receptor (Chen et al., 2014).

Previously, the different polymorphic modifications for close analogs of the ethosuximide (Lin et al., 2012) and phensuximide (Kuhnert-Brandstätter & Bösch, 1978) derivatives were found by powder X-ray diffraction, IR spectroscopy and DSC methods. In search of polymorphic modifications for methsuximide we have carried out the DSC study of the title compound. However, no peaks that correspond to phase transitions, except for melting, were observed.

Related literature top

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 top

1,3-Dimethyl-3-phenylpyrrolidine-2,5-dione (methsuximide, reference standard grade) was obtained under a Material Transfer Agreement with Pfizer Inc. and used without any further purification. The single crystals of the title compound were grown by slow evaporation of an EtOH/H₂O (3:1) solvent mixture at room temperature; m.p. = 328-332 K.

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: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title molecule, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. 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.

1,3-Dimethyl-3-phenylpyrrolidine-2,5-dione top

Crystal data top

C₁₂H₁₃NO₂	F(000) = 432
M_r = 203.23	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.051P)² + 0.2557P] where P = (F_o² + 2F_c²)/3
3170 reflections	(Δ/σ)_max < 0.001
138 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₂H₁₃NO₂	V = 1029.2 (8) Å³
M_r = 203.23	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.517 (5) Å	µ = 0.09 mm⁻¹
b = 7.383 (3) Å	T = 100 K
c = 13.568 (6) Å	0.45 × 0.35 × 0.25 mm
β = 102.332 (6)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3170 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2401 reflections with I > 2σ(I)
T_min = 0.961, T_max = 0.978	R_int = 0.039
11948 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.117	H-atom parameters constrained
S = 1.04	Δρ_max = 0.31 e Å⁻³
3170 reflections	Δρ_min = −0.20 e Å⁻³
138 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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

Acknowledgements

Funding from the US National Science Foundation (PREM DMR-0934212 and IIA-1301346) and the 2013–2020 Program aimed at maximizing the ITMO University's competitive advantage among the world's leading education centers 5/100 is gratefully acknowledged. We thank Dr Arcadius V. Krivoshein (Albany College of Pharmacy & Health Sciences, Albany, New York) for providing us with methsuximide and help in obtaining the single crystals for this investigation.

References

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Volume 70| Part 9| September 2014| Pages o942-o943

doi:10.1107/S1600536814016717

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of 1,3-di­methyl-3-phenyl­pyrrolidine-2,5-dione: a clinically used anti­convulsant

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of 1,3-dimethyl-3-phenylpyrrolidine-2,5-dione: a clinically used anticonvulsant