3-Methyl-5,5-di­phenyl­imidazolidine-2,4-dione

Guerrab, W.; Akrad, R.; Ansar, M.; Taoufik, J.; Mague, J.T.; Ramli, Y.

doi:10.1107/S2414314617015346

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 10| October 2017| x171534

https://doi.org/10.1107/S2414314617015346

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3-Methyl-5,5-diphenylimidazolidine-2,4-dione

Walid Guerrab,^a ^* Rachida Akrad,^a Mhammed Ansar,^a Jamal Taoufik,^a Joel T. Mague ^b and Youssef Ramli ^a

^aLaboratory of Medicinal Chemistry, Faculty of Medicine and Pharmacy, Mohammed V University, Rabat, Morocco, and ^bDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
^*Correspondence e-mail: gerrab_walid@yahoo.com

Edited by J. Simpson, University of Otago, New Zealand (Received 14 October 2017; accepted 21 October 2017; online 27 October 2017)

In the title molecule, C₁₆H₁₄N₂O₂, the imidazolidine-2,4-dione ring carries two phenyl substituents at the 5-position inclined to the five-membered ring plane by 59.17 (6) and 53.21 (6)°. In the crystal, the molecules form chains parallel to the a-axis direction through N—H⋯O hydrogen bonds. These chains are linked into a three-dimensional network of molecules stacked along a through C—H⋯π(ring) interactions.

Keywords: crystal structure; hydantoin; imidazolidine-2,4-dione; hydrogen bonding; C—H⋯π(ring) interactions.

CCDC reference: 1581286

Structure description

Hydantoin, also known as imidazolidin-2,4-dione, is an important nucleus found in numerous natural products and in several clinically important medicines. One the best known examples of such a derivative is phenytoine (5,5-diphenylimidazolidine-2,4-dion), a drug widely prescribed as an anticonvulsant agent and for the treatment of many other diseases including HIV (Weichet, 1974 ; Havera & Strycker, 1976 ; Khodair et al., 1997 ; Thenmozhiyal et al., 2004 ). As a continuation of our work in this area (Ramli et al., 2017a ,b ; Akrad et al. 2017 ), the compound N-methyl-5,5-diphenylimidazolidine-2,4-dion (Fig. 1) was prepared and its crystal structure is reported here.

Figure 1
The title molecule with the labelling scheme and 50% probability displacement ellipsoids.

The C1,N2,C3,N1,C2 imidazolidine-2,4-dione ring carries two phenyl substituents on C1. These are inclined to the five-membered ring plane by 59.17 (6)° (C5–C10) and 53.21 (6)° (C11–C16). In the crystal, molecules forms chains parallel to the a-axis direction through N2—H2⋯O1 hydrogen bonds. These chains form a three-dimensional network of molecules stacked along a through a series of C—H⋯π interactions, Table 1, Figs. 2 and 3.

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C5–C10 and C11–C16 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1ⁱ	0.928 (19)	1.922 (19)	2.8482 (13)	175.9 (16)
C4—H4E⋯Cg3ⁱⁱ	0.98	2.87	3.5883 (14)	131
C8—H8⋯Cg3ⁱⁱⁱ	0.922 (19)	2.915 (19)	3.7061 (14)	144.7 (14)
C13—H15⋯Cg2^iv	0.997 (19)	2.809 (19)	139.8 (14)	3.6255 (15)
Symmetry codes: (i) x+1, y, z; (ii) $[x-{\script{3\over 2}}, -y-{\script{1\over 2}}, z-{\script{3\over 2}}]$ ; (iii) $[x-{\script{1\over 2}}, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iv) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Figure 2
C—H⋯π(ring) contacts in the title structure, shown as green dashed lines.

Figure 3
Packing of the title compound viewed along the b-axis direction, with N—H⋯O hydrogen drawn as blue dashed lines.

Synthesis and crystallization

To a solution of 5,5-diphenylimidazolidine-2,4-dione (1 g, 3.96 mmol) was added one equivalent of methyl bromide (0.37 g) in absolute DMF and the solution was heated under reflux for 3 h in the presence of 1.3 equivalents of K₂CO₃. The reaction mixture was filtered while hot, and the solvent was distilled off under reduced pressure. The residue obtained was dried and recrystallized from ethanol solution.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The C4 methyl group is rotationally disordered over two sets of sites of equal occupancy.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₆H₁₄N₂O₂
M_r	266.29
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	150
a, b, c (Å)	6.2328 (3), 15.7965 (7), 13.4448 (6)
β (°)	95.256 (1)
V (Å³)	1318.16 (10)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	0.73
Crystal size (mm)	0.27 × 0.17 × 0.11

Data collection
Diffractometer	Bruker D8 VENTURE PHOTON 100 CMOS
Absorption correction	Multi-scan (SADABS; Bruker, 2016 )
T_min, T_max	0.84, 0.93
No. of measured, independent and observed [I > 2σ(I)] reflections	10021, 2636, 2455
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.094, 1.07
No. of reflections	2636
No. of parameters	226
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.16
Computer programs: APEX3 and SAINT (Bruker, 2016), SHELXT (Sheldrick, 2015a ), SHELXL2016 (Sheldrick, 2015b ), DIAMOND (Brandenburg & Putz, 2012 ) and SHELXTL (Sheldrick, 2008 ).

Structural data

CCDC reference: 1581286

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314617015346/sj4141sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617015346/sj4141Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617015346/sj4141Isup3.cml

checkCIF report

Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

3-Methyl-5,5-diphenylimidazolidine-2,4-dione top

Crystal data top

C₁₆H₁₄N₂O₂	F(000) = 560
M_r = 266.29	D_x = 1.342 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54178 Å
a = 6.2328 (3) Å	Cell parameters from 8452 reflections
b = 15.7965 (7) Å	θ = 3.3–74.3°
c = 13.4448 (6) Å	µ = 0.73 mm⁻¹
β = 95.256 (1)°	T = 150 K
V = 1318.16 (10) Å³	Block, colourless
Z = 4	0.27 × 0.17 × 0.11 mm

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	2636 independent reflections
Radiation source: INCOATEC IµS micro-focus source	2455 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.029
Detector resolution: 10.4167 pixels mm^-1	θ_max = 74.3°, θ_min = 4.3°
ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −18→15
T_min = 0.84, T_max = 0.93	l = −16→16
10021 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.094	w = 1/[σ²(F_o²) + (0.0432P)² + 0.4502P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
2636 reflections	Δρ_max = 0.22 e Å⁻³
226 parameters	Δρ_min = −0.16 e Å⁻³
0 restraints	Extinction correction: SHELXL2016 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0076 (7)

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. The methyl group is rotationally disordered over two approximately equal sites. These hydrogen atoms were included as riding contributions with an HFIX 123 instruction.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.13255 (13)	0.20890 (6)	0.18291 (6)	0.0256 (2)
O2	0.66323 (15)	0.11602 (7)	−0.00232 (7)	0.0357 (3)
N1	0.35876 (15)	0.15080 (7)	0.07600 (7)	0.0229 (2)
N2	0.67715 (16)	0.19646 (6)	0.14190 (7)	0.0223 (2)
H2	0.826 (3)	0.1992 (11)	0.1523 (13)	0.040 (4)*
C1	0.52715 (17)	0.22587 (7)	0.21171 (8)	0.0191 (2)
C2	0.31218 (18)	0.19529 (7)	0.15712 (8)	0.0202 (2)
C3	0.58171 (19)	0.15088 (8)	0.06526 (9)	0.0237 (3)
C4	0.2018 (2)	0.11254 (9)	0.00207 (10)	0.0327 (3)
H4A	0.277440	0.083919	−0.049134	0.049*	0.5
H4B	0.114417	0.071292	0.034962	0.049*	0.5
H4C	0.108029	0.156724	−0.029217	0.049*	0.5
H4D	0.055817	0.124037	0.020207	0.049*	0.5
H4E	0.218840	0.136665	−0.063888	0.049*	0.5
H4F	0.225229	0.051233	0.000291	0.049*	0.5
C5	0.57456 (18)	0.18436 (7)	0.31480 (8)	0.0204 (3)
C6	0.7833 (2)	0.19301 (8)	0.36193 (9)	0.0243 (3)
H6	0.890 (3)	0.2240 (10)	0.3288 (12)	0.036 (4)*
C7	0.8360 (2)	0.15792 (8)	0.45565 (9)	0.0296 (3)
H7	0.987 (3)	0.1627 (10)	0.4875 (12)	0.035 (4)*
C8	0.6822 (2)	0.11504 (9)	0.50429 (10)	0.0318 (3)
H8	0.716 (3)	0.0918 (11)	0.5667 (14)	0.044 (5)*
C9	0.4749 (2)	0.10690 (9)	0.45810 (10)	0.0313 (3)
H9	0.361 (3)	0.0771 (11)	0.4909 (13)	0.040 (4)*
C10	0.4207 (2)	0.14135 (8)	0.36395 (9)	0.0258 (3)
H10	0.275 (3)	0.1368 (10)	0.3333 (12)	0.034 (4)*
C11	0.52751 (18)	0.32217 (7)	0.22487 (8)	0.0202 (2)
C12	0.6895 (2)	0.37174 (8)	0.19058 (9)	0.0274 (3)
H12	0.257 (3)	0.3252 (10)	0.3030 (12)	0.032 (4)*
C13	0.6913 (2)	0.45887 (9)	0.20707 (11)	0.0349 (3)
H13	0.254 (3)	0.4735 (11)	0.3275 (12)	0.039 (4)*
C14	0.5318 (2)	0.49661 (8)	0.25678 (10)	0.0328 (3)
H14	0.537 (3)	0.5566 (13)	0.2694 (13)	0.047 (5)*
C15	0.3708 (2)	0.44727 (8)	0.29156 (10)	0.0295 (3)
H15	0.809 (3)	0.4931 (12)	0.1821 (14)	0.050 (5)*
C16	0.3694 (2)	0.36034 (8)	0.27661 (9)	0.0246 (3)
H16	0.807 (3)	0.3452 (11)	0.1544 (12)	0.038 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0165 (4)	0.0345 (5)	0.0258 (4)	−0.0012 (3)	0.0014 (3)	−0.0014 (3)
O2	0.0294 (5)	0.0497 (6)	0.0285 (5)	−0.0012 (4)	0.0061 (4)	−0.0156 (4)
N1	0.0190 (5)	0.0295 (5)	0.0197 (5)	−0.0030 (4)	−0.0007 (4)	−0.0035 (4)
N2	0.0165 (5)	0.0309 (5)	0.0194 (5)	0.0003 (4)	0.0016 (4)	−0.0044 (4)
C1	0.0156 (5)	0.0240 (6)	0.0177 (5)	0.0000 (4)	0.0011 (4)	−0.0006 (4)
C2	0.0187 (5)	0.0232 (6)	0.0182 (5)	−0.0010 (4)	0.0000 (4)	0.0017 (4)
C3	0.0215 (6)	0.0285 (6)	0.0211 (6)	−0.0002 (4)	0.0021 (4)	−0.0020 (4)
C4	0.0284 (7)	0.0433 (8)	0.0251 (6)	−0.0095 (5)	−0.0042 (5)	−0.0069 (5)
C5	0.0222 (6)	0.0203 (5)	0.0183 (5)	0.0025 (4)	0.0010 (4)	−0.0014 (4)
C6	0.0234 (6)	0.0270 (6)	0.0221 (6)	0.0009 (5)	−0.0006 (4)	−0.0008 (4)
C7	0.0319 (7)	0.0320 (7)	0.0234 (6)	0.0041 (5)	−0.0055 (5)	−0.0025 (5)
C8	0.0446 (8)	0.0304 (7)	0.0193 (6)	0.0048 (5)	−0.0019 (5)	0.0022 (5)
C9	0.0378 (7)	0.0320 (7)	0.0247 (6)	−0.0010 (5)	0.0064 (5)	0.0042 (5)
C10	0.0243 (6)	0.0293 (6)	0.0236 (6)	−0.0001 (5)	0.0013 (5)	0.0017 (5)
C11	0.0206 (5)	0.0237 (6)	0.0157 (5)	−0.0004 (4)	−0.0020 (4)	0.0008 (4)
C12	0.0279 (6)	0.0286 (7)	0.0259 (6)	−0.0033 (5)	0.0044 (5)	0.0020 (5)
C13	0.0405 (8)	0.0284 (7)	0.0364 (7)	−0.0084 (6)	0.0059 (6)	0.0040 (5)
C14	0.0448 (8)	0.0219 (7)	0.0308 (7)	−0.0005 (5)	−0.0015 (6)	0.0008 (5)
C15	0.0343 (7)	0.0279 (7)	0.0257 (6)	0.0056 (5)	0.0003 (5)	−0.0025 (5)
C16	0.0251 (6)	0.0269 (6)	0.0216 (6)	0.0003 (5)	0.0012 (4)	−0.0004 (4)

Geometric parameters (Å, º) top

O1—C2	1.2211 (14)	C6—H6	0.969 (17)
O2—C3	1.2130 (15)	C7—C8	1.386 (2)
N1—C2	1.3513 (15)	C7—H7	0.999 (17)
N1—C3	1.4102 (15)	C8—C9	1.387 (2)
N1—C4	1.4603 (15)	C8—H8	0.922 (19)
N2—C3	1.3497 (15)	C9—C10	1.3908 (18)
N2—C1	1.4600 (14)	C9—H9	0.987 (17)
N2—H2	0.928 (19)	C10—H10	0.965 (16)
C1—C11	1.5314 (16)	C11—C12	1.3894 (16)
C1—C5	1.5374 (15)	C11—C16	1.3944 (16)
C1—C2	1.5450 (15)	C12—C13	1.3940 (19)
C4—H4A	0.9800	C12—H16	1.007 (17)
C4—H4B	0.9800	C13—C14	1.383 (2)
C4—H4C	0.9800	C13—H15	0.997 (19)
C4—H4D	0.9800	C14—C15	1.386 (2)
C4—H4E	0.9800	C14—H14	0.96 (2)
C4—H4F	0.9800	C15—C16	1.3878 (18)
C5—C10	1.3905 (17)	C15—H13	0.999 (16)
C5—C6	1.4004 (16)	C16—H12	0.987 (16)
C6—C7	1.3883 (17)

C2—N1—C3	111.64 (9)	H4E—C4—H4F	109.5
C2—N1—C4	125.77 (10)	C10—C5—C6	119.02 (11)
C3—N1—C4	122.41 (10)	C10—C5—C1	123.56 (10)
C3—N2—C1	113.40 (9)	C6—C5—C1	117.39 (10)
C3—N2—H2	120.4 (10)	C7—C6—C5	120.30 (12)
C1—N2—H2	125.4 (10)	C7—C6—H6	120.2 (10)
N2—C1—C11	113.33 (9)	C5—C6—H6	119.5 (10)
N2—C1—C5	111.24 (9)	C8—C7—C6	120.47 (12)
C11—C1—C5	108.75 (9)	C8—C7—H7	119.9 (9)
N2—C1—C2	100.01 (9)	C6—C7—H7	119.6 (9)
C11—C1—C2	110.95 (9)	C7—C8—C9	119.36 (12)
C5—C1—C2	112.43 (9)	C7—C8—H8	120.9 (11)
O1—C2—N1	126.24 (10)	C9—C8—H8	119.8 (11)
O1—C2—C1	126.01 (10)	C8—C9—C10	120.64 (12)
N1—C2—C1	107.75 (9)	C8—C9—H9	121.3 (10)
O2—C3—N2	128.93 (11)	C10—C9—H9	118.0 (10)
O2—C3—N1	124.09 (11)	C5—C10—C9	120.22 (12)
N2—C3—N1	106.97 (10)	C5—C10—H10	119.7 (9)
N1—C4—H4A	109.5	C9—C10—H10	120.0 (9)
N1—C4—H4B	109.5	C12—C11—C16	119.35 (11)
H4A—C4—H4B	109.5	C12—C11—C1	120.99 (10)
N1—C4—H4C	109.5	C16—C11—C1	119.57 (10)
H4A—C4—H4C	109.5	C11—C12—C13	119.94 (12)
H4B—C4—H4C	109.5	C11—C12—H16	120.6 (10)
N1—C4—H4D	109.5	C13—C12—H16	119.5 (10)
H4A—C4—H4D	141.1	C14—C13—C12	120.47 (12)
H4B—C4—H4D	56.3	C14—C13—H15	121.0 (11)
H4C—C4—H4D	56.3	C12—C13—H15	118.6 (11)
N1—C4—H4E	109.5	C13—C14—C15	119.71 (12)
H4A—C4—H4E	56.3	C13—C14—H14	119.7 (11)
H4B—C4—H4E	141.1	C15—C14—H14	120.6 (11)
H4C—C4—H4E	56.3	C14—C15—C16	120.18 (12)
H4D—C4—H4E	109.5	C14—C15—H13	120.7 (10)
N1—C4—H4F	109.5	C16—C15—H13	119.1 (10)
H4A—C4—H4F	56.3	C15—C16—C11	120.32 (12)
H4B—C4—H4F	56.3	C15—C16—H12	120.0 (9)
H4C—C4—H4F	141.1	C11—C16—H12	119.7 (9)
H4D—C4—H4F	109.5

C3—N2—C1—C11	−122.82 (11)	C2—C1—C5—C6	166.81 (10)
C3—N2—C1—C5	114.28 (11)	C10—C5—C6—C7	1.00 (17)
C3—N2—C1—C2	−4.69 (12)	C1—C5—C6—C7	179.22 (11)
C3—N1—C2—O1	176.95 (11)	C5—C6—C7—C8	−0.96 (19)
C4—N1—C2—O1	1.9 (2)	C6—C7—C8—C9	0.5 (2)
C3—N1—C2—C1	−3.13 (13)	C7—C8—C9—C10	−0.1 (2)
C4—N1—C2—C1	−178.20 (11)	C6—C5—C10—C9	−0.59 (18)
N2—C1—C2—O1	−175.55 (11)	C1—C5—C10—C9	−178.69 (11)
C11—C1—C2—O1	−55.66 (15)	C8—C9—C10—C5	0.1 (2)
C5—C1—C2—O1	66.36 (15)	N2—C1—C11—C12	−13.45 (15)
N2—C1—C2—N1	4.54 (11)	C5—C1—C11—C12	110.82 (11)
C11—C1—C2—N1	124.42 (10)	C2—C1—C11—C12	−125.02 (11)
C5—C1—C2—N1	−113.55 (10)	N2—C1—C11—C16	169.94 (10)
C1—N2—C3—O2	−177.48 (13)	C5—C1—C11—C16	−65.79 (13)
C1—N2—C3—N1	3.15 (14)	C2—C1—C11—C16	58.36 (13)
C2—N1—C3—O2	−179.23 (12)	C16—C11—C12—C13	−0.74 (18)
C4—N1—C3—O2	−4.0 (2)	C1—C11—C12—C13	−177.36 (11)
C2—N1—C3—N2	0.17 (14)	C11—C12—C13—C14	−0.5 (2)
C4—N1—C3—N2	175.43 (11)	C12—C13—C14—C15	0.8 (2)
N2—C1—C5—C10	−126.29 (12)	C13—C14—C15—C16	0.0 (2)
C11—C1—C5—C10	108.21 (12)	C14—C15—C16—C11	−1.23 (19)
C2—C1—C5—C10	−15.06 (15)	C12—C11—C16—C15	1.58 (17)
N2—C1—C5—C6	55.57 (13)	C1—C11—C16—C15	178.25 (11)
C11—C1—C5—C6	−69.93 (12)

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg3 are the centroids of the C5–C10 and C11–C16 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1ⁱ	0.928 (19)	1.922 (19)	2.8482 (13)	175.9 (16)
C4—H4E···Cg3ⁱⁱ	0.98	2.87	3.5883 (14)	131
C8—H8···Cg3ⁱⁱⁱ	0.922 (19)	2.915 (19)	3.7061 (14)	144.7 (14)
C13—H15···Cg2^iv	0.997 (19)	2.809 (19)	139.8 (14)	3.6255 (15)

Symmetry codes: (i) x+1, y, z; (ii) x−3/2, −y−1/2, z−3/2; (iii) x−1/2, −y−1/2, z−1/2; (iv) −x+3/2, y+1/2, −z+1/2.

Acknowledgements

The support of NSF–MRI Grant No. 1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged.

References

Akrad, R., Mague, J. T., Guerrab, W., Taoufik, J., Ansar, M. & Ramli, Y. (2017). IUCrData, 2, x170033. Google Scholar
Brandenburg, K. & Putz, H. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2016). APEX3, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Havera, H. J. & Strycker, W. G. (1976). US Patent 3 904 909. Google Scholar
Khodair, A. I., el-Subbagh, H. I. & el-Emam, A. A. (1997). Boll. Chim. Farm. 136, 561–567. CAS PubMed Google Scholar
Ramli, Y., Akrad, R., Guerrab, W., Taoufik, J., Ansar, M. & Mague, J. T. (2017a). IUCrData, 2, x170098. Google Scholar
Ramli, Y., Guerrab, W., Moussaif, A., Taoufik, J., Essassi, E. M. & Mague, J. T. (2017b). IUCrData, 2, x171041. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Thenmozhiyal, J. C., Wong, P. T. H. & Chui, W.-K. (2004). J. Med. Chem. 47, 1527–1535. Web of Science CrossRef PubMed CAS Google Scholar
Weichet, B. L. (1974). Czech Patent 151,744–747. Google Scholar

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

3-Methyl-5,5-di­phenyl­imidazolidine-2,4-dione

Structure description

Synthesis and crystallization

Refinement

Structural data

Acknowledgements

References

organic compounds

3-Methyl-5,5-diphenylimidazolidine-2,4-dione