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

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.

Key indicators

• Single-crystal X-ray study
• T = 113 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.064
• wR factor = 0.151
• Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          1
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          7
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          2
PLAT716_ALERT_1_C H...A   Unknown or Inconsistent Label ..........          .
PLAT716_ALERT_1_C H...A   Unknown or Inconsistent Label ..........          .

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

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

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

S2. Experimental

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).

S3. Refinement

All C-bound H atoms were found on difference maps, but included in the final cycles of refinement using a riding model with C—H = 0.95–0.99 Å, and with U_iso(H) = 1.2U_eq(C) for aryl- and methylene-H atoms, and 1.5U_eq(C) for the methyl H atoms. The N–H1 atom was refined freely.

Computing details

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

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

Crystal data

C10H10N2O3	F(000) = 432
Mr = 206.20	Dx = 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) Å^3	0.24 × 0.12 × 0.10 mm
Z = 4

Data collection

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

Refinement

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

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^i	0.91 (1)	1.95 (1)	2.8512 (19)	172 (2)
C2—H2A···O2^ii	0.99	2.34	3.291 (2)	160
C8—H8···O2^iii	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.