1-(4-Methoxy­phen­yl)imidazolidine-2,4-dione

Sun, S.-X.; Zhang, H.; Cheng, X.-C.; Wang, R.-L.; Dong, W.-L.

doi:10.1107/S1600536810016478

organic compounds

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ISSN: 2056-9890

Volume 66| Part 6| June 2010| Page o1308

https://doi.org/10.1107/S1600536810016478

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1-(4-Methoxyphenyl)imidazolidine-2,4-dione

Su-Xia Sun,^a Hao Zhang,^a Xian-Chao Cheng,^a Run-Ling Wang ^a ^* and Wei-Li Dong ^a

^aSchool of Pharmacy, Tianjin Medical University, Tianjin 300070, People's Republic of China
^*Correspondence e-mail: wangrunling2008@yahoo.cn

(Received 28 April 2010; accepted 5 May 2010; online 12 May 2010)

In the title compound, C₁₀H₁₀N₂O₃, the dihedral angle between the benzene and imidazolidine rings is 6.0 (4)°, consistent with an essentially planar molecule. In the crystal, intermolecular N—H⋯O hydrogen bonding between centrosymmetrically related molecules leads to loosely associated dimeric aggregates. These are connected into a three-dimensional network by C—H⋯O interactions, as well as π–π interactions [centroid–centroid distances = 3.705 (3) and 3.622 (3) Å] between the imidazolidine and benzene rings.

Related literature

For related structures, see: Gerdil (1960 ). For the synthesis, see: Niwata et al. (1997 ); Kurzer et al. (1963 ).

Experimental

Crystal data

C₁₀H₁₀N₂O₃
M_r = 206.20
Monoclinic, P 2₁ /c
a = 4.9993 (10) Å
b = 6.1566 (12) Å
c = 30.052 (6) Å
β = 93.91 (3)°
V = 922.8 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 113 K
0.24 × 0.12 × 0.10 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ) T_min = 0.974, T_max = 0.989
6955 measured reflections
2203 independent reflections
1507 reflections with I > 2σ(I)
R_int = 0.078

Refinement

R[F² > 2σ(F²)] = 0.064
wR(F²) = 0.151
S = 1.05
2203 reflections
142 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.91 (1)	1.95 (1)	2.8512 (19)	172 (2)
C2—H2A⋯O2ⁱⁱ	0.99	2.34	3.291 (2)	160
C8—H8⋯O2ⁱⁱⁱ	0.95	2.42	3.203 (2)	140
Symmetry codes: (i) -x, -y, -z+1; (ii) x, y+1, z; (iii) x+1, y+1, z.

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810016478/tk2669sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810016478/tk2669Isup2.hkl

checkCIF report

Comment top

During an investigation of new anti-diabetic drugs, we found that imidazolidinediones (IZD's) have good anti-diabetic activities. The crystal structure determination of the title compound, (I), was undertaken to investigate the relationship between structure and anti-diabetic activity.

In title compound, C₁₀H₁₀N₂O₃, bond lengths and angles are normal and in a good agreement with those reported previously (Gerdil, 1960). The dihedral angle between the benzene ring (C4—C9) and imidazolidine ring (C1—C3/N1/N2) is 6.0 (4) °. In the crystal packing, intermolecular N—H···O hydrogen bonding between centrosymmetrically related molecules lead to loosely associated dimeric aggregates, Table 1. These aggregates are connected into the 3-D crystal structure by C—H···O and π–π interactions, the latter occurring between the imidazolidine and benzene rings, Table 1.

Related literature top

For related structures, see: Gerdil (1960). For the synthesis, see: Niwata et al. (1997); Kurzer et al. (1963).

Experimental top

Compound (I) (1.13 g, 55% yield) was prepared according to the reported procedure of (Niwata et al., 1997), using 1-(4-methoxyphenyl)urea (0.010 mol; Kurzer et al., 1963), sodium hydride (0.022 mol), N,N-dimethylformamide (20 ml), and ethyl chloroacetate (0.0120 mol. Colourless single crystals suitable for X-ray diffraction analysis were obtained by recrystallization from a mixture of methanol and water (1:1 V/V).

Structure description top

For related structures, see: Gerdil (1960). For the synthesis, see: Niwata et al. (1997); Kurzer et al. (1963).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. View of the title compound showing atom labelling, with displacement ellipsoids drawn at the 40% probability level.

1-(4-Methoxyphenyl)imidazolidine-2,4-dione top

Crystal data top

C₁₀H₁₀N₂O₃	F(000) = 432
M_r = 206.20	D_x = 1.484 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 196 reflections
a = 4.9993 (10) Å	θ = 2.0–27.9°
b = 6.1566 (12) Å	µ = 0.11 mm⁻¹
c = 30.052 (6) Å	T = 113 K
β = 93.91 (3)°	Prism, colourless
V = 922.8 (3) Å³	0.24 × 0.12 × 0.10 mm
Z = 4

Data collection top

Rigaku Saturn CCD area-detector diffractometer	2203 independent reflections
Radiation source: rotating anode	1507 reflections with I > 2σ(I)
Multilayer monochromator	R_int = 0.078
Detector resolution: 7.31 pixels mm^-1	θ_max = 27.9°, θ_min = 2.7°
ω and φ scans	h = −6→4
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −8→7
T_min = 0.974, T_max = 0.989	l = −34→39
6955 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.064	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.151	w = 1/[σ²(F_o²) + (0.0718P)²] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
2203 reflections	Δρ_max = 0.44 e Å⁻³
142 parameters	Δρ_min = −0.40 e Å⁻³
1 restraint	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 1.95 (8)

Crystal data top

C₁₀H₁₀N₂O₃	V = 922.8 (3) Å³
M_r = 206.20	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 4.9993 (10) Å	µ = 0.11 mm⁻¹
b = 6.1566 (12) Å	T = 113 K
c = 30.052 (6) Å	0.24 × 0.12 × 0.10 mm
β = 93.91 (3)°

Data collection top

Rigaku Saturn CCD area-detector diffractometer	2203 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	1507 reflections with I > 2σ(I)
T_min = 0.974, T_max = 0.989	R_int = 0.078
6955 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	1 restraint
wR(F²) = 0.151	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.44 e Å⁻³
2203 reflections	Δρ_min = −0.40 e Å⁻³
142 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 > σ(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	0.1590 (2)	0.2744 (2)	0.50596 (4)	0.0270 (4)
O2	0.4023 (2)	−0.2177 (2)	0.40235 (4)	0.0286 (4)
O3	1.2460 (3)	0.2947 (2)	0.28363 (4)	0.0303 (4)
N1	0.2393 (3)	−0.0069 (2)	0.45821 (5)	0.0232 (4)
N2	0.5536 (3)	0.1341 (2)	0.41800 (5)	0.0217 (4)
C1	0.2749 (3)	0.1953 (3)	0.47530 (6)	0.0221 (4)
C2	0.4866 (3)	0.3027 (3)	0.44955 (5)	0.0213 (4)
H2A	0.4155	0.4340	0.4338	0.026*
H2B	0.6448	0.3433	0.4694	0.026*
C3	0.4027 (3)	−0.0471 (3)	0.42284 (6)	0.0221 (4)
C4	0.7341 (3)	0.1737 (3)	0.38439 (5)	0.0209 (4)
C5	0.7790 (3)	0.0195 (3)	0.35134 (6)	0.0265 (4)
H5	0.6900	−0.1168	0.3514	0.032*
C6	0.9526 (3)	0.0659 (3)	0.31876 (6)	0.0272 (5)
H6	0.9814	−0.0391	0.2964	0.033*
C7	1.0854 (3)	0.2637 (3)	0.31826 (6)	0.0236 (4)
C8	1.0464 (3)	0.4155 (3)	0.35116 (6)	0.0244 (4)
H8	1.1385	0.5505	0.3513	0.029*
C9	0.8710 (3)	0.3692 (3)	0.38415 (6)	0.0230 (4)
H9	0.8452	0.4735	0.4068	0.028*
C10	1.3963 (4)	0.4914 (3)	0.28380 (7)	0.0339 (5)
H10A	1.2732	0.6153	0.2811	0.051*
H10B	1.5108	0.4915	0.2586	0.051*
H10C	1.5082	0.5027	0.3118	0.051*
H1	0.113 (3)	−0.100 (3)	0.4673 (7)	0.045 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0294 (7)	0.0210 (8)	0.0312 (7)	−0.0022 (5)	0.0070 (5)	−0.0019 (6)
O2	0.0365 (7)	0.0170 (8)	0.0321 (7)	−0.0036 (5)	0.0020 (5)	−0.0035 (5)
O3	0.0331 (7)	0.0295 (9)	0.0295 (7)	−0.0001 (5)	0.0103 (5)	−0.0008 (6)
N1	0.0260 (7)	0.0171 (9)	0.0264 (8)	−0.0035 (5)	0.0012 (6)	0.0003 (6)
N2	0.0269 (8)	0.0151 (8)	0.0232 (8)	−0.0022 (5)	0.0035 (6)	−0.0020 (6)
C1	0.0243 (8)	0.0183 (10)	0.0231 (8)	−0.0002 (6)	−0.0027 (6)	0.0020 (7)
C2	0.0263 (8)	0.0152 (9)	0.0226 (9)	−0.0019 (6)	0.0031 (6)	−0.0019 (7)
C3	0.0253 (8)	0.0171 (10)	0.0235 (9)	−0.0010 (6)	−0.0022 (6)	0.0001 (7)
C4	0.0226 (8)	0.0184 (10)	0.0212 (8)	0.0021 (6)	−0.0006 (6)	0.0015 (7)
C5	0.0320 (9)	0.0181 (10)	0.0295 (10)	−0.0007 (7)	0.0022 (7)	−0.0018 (7)
C6	0.0339 (10)	0.0229 (10)	0.0249 (9)	0.0025 (7)	0.0026 (7)	−0.0038 (8)
C7	0.0219 (9)	0.0259 (11)	0.0229 (9)	0.0041 (6)	0.0011 (6)	0.0022 (7)
C8	0.0256 (9)	0.0216 (10)	0.0259 (9)	−0.0029 (6)	−0.0004 (7)	0.0004 (7)
C9	0.0267 (9)	0.0193 (10)	0.0226 (8)	−0.0008 (6)	−0.0001 (6)	−0.0020 (7)
C10	0.0310 (10)	0.0359 (13)	0.0353 (11)	−0.0048 (8)	0.0067 (8)	0.0036 (9)

Geometric parameters (Å, º) top

O1—C1	1.223 (2)	C4—C9	1.385 (2)
O2—C3	1.217 (2)	C4—C5	1.403 (2)
O3—C7	1.370 (2)	C5—C6	1.382 (2)
O3—C10	1.425 (2)	C5—H5	0.9500
N1—C1	1.354 (2)	C6—C7	1.388 (3)
N1—C3	1.406 (2)	C6—H6	0.9500
N1—H1	0.911 (10)	C7—C8	1.384 (2)
N2—C3	1.360 (2)	C8—C9	1.397 (2)
N2—C4	1.420 (2)	C8—H8	0.9500
N2—C2	1.460 (2)	C9—H9	0.9500
C1—C2	1.506 (2)	C10—H10A	0.9800
C2—H2A	0.9900	C10—H10B	0.9800
C2—H2B	0.9900	C10—H10C	0.9800

C7—O3—C10	116.85 (14)	C6—C5—C4	120.02 (17)
C1—N1—C3	112.37 (14)	C6—C5—H5	120.0
C1—N1—H1	122.9 (15)	C4—C5—H5	120.0
C3—N1—H1	124.5 (15)	C5—C6—C7	120.87 (17)
C3—N2—C4	126.92 (15)	C5—C6—H6	119.6
C3—N2—C2	111.09 (14)	C7—C6—H6	119.6
C4—N2—C2	121.66 (14)	O3—C7—C8	124.53 (17)
O1—C1—N1	126.52 (17)	O3—C7—C6	115.84 (16)
O1—C1—C2	126.75 (17)	C8—C7—C6	119.62 (16)
N1—C1—C2	106.72 (15)	C7—C8—C9	119.67 (17)
N2—C2—C1	102.84 (14)	C7—C8—H8	120.2
N2—C2—H2A	111.2	C9—C8—H8	120.2
C1—C2—H2A	111.2	C4—C9—C8	121.02 (16)
N2—C2—H2B	111.2	C4—C9—H9	119.5
C1—C2—H2B	111.2	C8—C9—H9	119.5
H2A—C2—H2B	109.1	O3—C10—H10A	109.5
O2—C3—N2	129.43 (17)	O3—C10—H10B	109.5
O2—C3—N1	123.60 (16)	H10A—C10—H10B	109.5
N2—C3—N1	106.95 (14)	O3—C10—H10C	109.5
C9—C4—C5	118.78 (16)	H10A—C10—H10C	109.5
C9—C4—N2	119.40 (15)	H10B—C10—H10C	109.5
C5—C4—N2	121.82 (16)

C3—N1—C1—O1	179.61 (16)	C3—N2—C4—C5	−0.8 (3)
C3—N1—C1—C2	−0.94 (18)	C2—N2—C4—C5	−173.66 (15)
C3—N2—C2—C1	1.19 (18)	C9—C4—C5—C6	−1.4 (2)
C4—N2—C2—C1	175.05 (14)	N2—C4—C5—C6	178.85 (15)
O1—C1—C2—N2	179.32 (16)	C4—C5—C6—C7	0.3 (3)
N1—C1—C2—N2	−0.13 (17)	C10—O3—C7—C8	4.6 (2)
C4—N2—C3—O2	6.1 (3)	C10—O3—C7—C6	−176.52 (15)
C2—N2—C3—O2	179.53 (17)	C5—C6—C7—O3	−178.02 (15)
C4—N2—C3—N1	−175.22 (14)	C5—C6—C7—C8	0.9 (3)
C2—N2—C3—N1	−1.77 (19)	O3—C7—C8—C9	177.92 (14)
C1—N1—C3—O2	−179.49 (15)	C6—C7—C8—C9	−0.9 (2)
C1—N1—C3—N2	1.71 (19)	C5—C4—C9—C8	1.4 (3)
C3—N2—C4—C9	179.43 (16)	N2—C4—C9—C8	−178.85 (14)
C2—N2—C4—C9	6.6 (2)	C7—C8—C9—C4	−0.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.91 (1)	1.95 (1)	2.8512 (19)	172 (2)
C2—H2A···O2ⁱⁱ	0.99	2.34	3.291 (2)	160
C8—H8···O2ⁱⁱⁱ	0.95	2.42	3.203 (2)	140
Cg1···Cg1^iv			3.705 (3)
Cg1···Cg2^v			3.622 (3)

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

Experimental details

Crystal data
Chemical formula	C₁₀H₁₀N₂O₃
M_r	206.20
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	113
a, b, c (Å)	4.9993 (10), 6.1566 (12), 30.052 (6)
β (°)	93.91 (3)
V (Å³)	922.8 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.24 × 0.12 × 0.10

Data collection
Diffractometer	Rigaku Saturn CCD area-detector
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.974, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	6955, 2203, 1507
R_int	0.078
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.151, 1.05
No. of reflections	2203
No. of parameters	142
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.40

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.911 (10)	1.946 (10)	2.8512 (19)	172 (2)
C2—H2A···O2ⁱⁱ	0.99	2.34	3.291 (2)	160
C8—H8···O2ⁱⁱⁱ	0.95	2.42	3.203 (2)	140
Cg1···Cg1^iv	.	.	3.705 (3)	.
Cg1···Cg2^v	.	.	3.622 (3)	.

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

Acknowledgements

This project was supported by the National Natural Science Foundation of China under contract No. 20972112 and the Tianjin Key Program of Natural Science Foundation of China under contract No. 09JCZDJC21600.

References

Gerdil, R. (1960). Acta Cryst. 13, 165–166. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Kurzer, F., Arnold, R. T. & Krogh, L. C. (1963). Org. Synth. 4, 49. Google Scholar
Niwata, S., Fukami, H., Sumida, M., Ito, A., Kakutani, S., Saitoh, M., Suzuki, K., Imoto, M., Shibata, H., Imajo, S., Kiso, Y., Tanaka, T., Nakazato, H., Ishihara, T., Takai, S., Yamamoto, D., Shiota, N., Miyazaki, M., Okunishi, H., Kinoshita, A., Urata, H. & Arakawa, K. (1997). J. Med. Chem. 40, 2156–2163. CrossRef CAS PubMed Web of Science Google Scholar
Rigaku/MSC (2005). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar