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

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ISSN: 2056-9890

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

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 ππ 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[Gerdil, R. (1960). Acta Cryst. 13, 165-166.]). For the synthesis, see: Niwata et al. (1997[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.]); Kurzer et al. (1963[Kurzer, F., Arnold, R. T. & Krogh, L. C. (1963). Org. Synth. 4, 49.]).

[Scheme 1]

Experimental

Crystal data
  • C10H10N2O3

  • Mr = 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[Rigaku/MSC (2005). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.]) Tmin = 0.974, Tmax = 0.989

  • 6955 measured reflections

  • 2203 independent reflections

  • 1507 reflections with I > 2σ(I)

  • Rint = 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

  • Δρmax = 0.44 e Å−3

  • Δρmin = −0.40 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Rigaku/MSC (2005). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


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 ππ 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).

Refinement top

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 Uiso(H) = 1.2Ueq(C) for aryl- and methylene-H atoms, and 1.5Ueq(C) for the methyl H atoms. The N–H1 atom was refined freely.

Structure description 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 ππ interactions, the latter occurring between the imidazolidine and benzene rings, Table 1.

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
[Figure 1] 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
C10H10N2O3F(000) = 432
Mr = 206.20Dx = 1.484 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 196 reflections
a = 4.9993 (10) Åθ = 2.0–27.9°
b = 6.1566 (12) ŵ = 0.11 mm1
c = 30.052 (6) ÅT = 113 K
β = 93.91 (3)°Prism, colourless
V = 922.8 (3) Å30.24 × 0.12 × 0.10 mm
Z = 4
Data collection top
Rigaku Saturn CCD area-detector
diffractometer
2203 independent reflections
Radiation source: rotating anode1507 reflections with I > 2σ(I)
Multilayer monochromatorRint = 0.078
Detector resolution: 7.31 pixels mm-1θmax = 27.9°, θmin = 2.7°
ω and φ scansh = 64
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)
k = 87
Tmin = 0.974, Tmax = 0.989l = 3439
6955 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.064H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.151 w = 1/[σ2(Fo2) + (0.0718P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
2203 reflectionsΔρmax = 0.44 e Å3
142 parametersΔρmin = 0.40 e Å3
1 restraintExtinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 1.95 (8)
Crystal data top
C10H10N2O3V = 922.8 (3) Å3
Mr = 206.20Z = 4
Monoclinic, P21/cMo Kα radiation
a = 4.9993 (10) ŵ = 0.11 mm1
b = 6.1566 (12) ÅT = 113 K
c = 30.052 (6) Å0.24 × 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)
Tmin = 0.974, Tmax = 0.989Rint = 0.078
6955 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0641 restraint
wR(F2) = 0.151H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.44 e Å3
2203 reflectionsΔρmin = 0.40 e Å3
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
xyzUiso*/Ueq
O10.1590 (2)0.2744 (2)0.50596 (4)0.0270 (4)
O20.4023 (2)0.2177 (2)0.40235 (4)0.0286 (4)
O31.2460 (3)0.2947 (2)0.28363 (4)0.0303 (4)
N10.2393 (3)0.0069 (2)0.45821 (5)0.0232 (4)
N20.5536 (3)0.1341 (2)0.41800 (5)0.0217 (4)
C10.2749 (3)0.1953 (3)0.47530 (6)0.0221 (4)
C20.4866 (3)0.3027 (3)0.44955 (5)0.0213 (4)
H2A0.41550.43400.43380.026*
H2B0.64480.34330.46940.026*
C30.4027 (3)0.0471 (3)0.42284 (6)0.0221 (4)
C40.7341 (3)0.1737 (3)0.38439 (5)0.0209 (4)
C50.7790 (3)0.0195 (3)0.35134 (6)0.0265 (4)
H50.69000.11680.35140.032*
C60.9526 (3)0.0659 (3)0.31876 (6)0.0272 (5)
H60.98140.03910.29640.033*
C71.0854 (3)0.2637 (3)0.31826 (6)0.0236 (4)
C81.0464 (3)0.4155 (3)0.35116 (6)0.0244 (4)
H81.13850.55050.35130.029*
C90.8710 (3)0.3692 (3)0.38415 (6)0.0230 (4)
H90.84520.47350.40680.028*
C101.3963 (4)0.4914 (3)0.28380 (7)0.0339 (5)
H10A1.27320.61530.28110.051*
H10B1.51080.49150.25860.051*
H10C1.50820.50270.31180.051*
H10.113 (3)0.100 (3)0.4673 (7)0.045 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0294 (7)0.0210 (8)0.0312 (7)0.0022 (5)0.0070 (5)0.0019 (6)
O20.0365 (7)0.0170 (8)0.0321 (7)0.0036 (5)0.0020 (5)0.0035 (5)
O30.0331 (7)0.0295 (9)0.0295 (7)0.0001 (5)0.0103 (5)0.0008 (6)
N10.0260 (7)0.0171 (9)0.0264 (8)0.0035 (5)0.0012 (6)0.0003 (6)
N20.0269 (8)0.0151 (8)0.0232 (8)0.0022 (5)0.0035 (6)0.0020 (6)
C10.0243 (8)0.0183 (10)0.0231 (8)0.0002 (6)0.0027 (6)0.0020 (7)
C20.0263 (8)0.0152 (9)0.0226 (9)0.0019 (6)0.0031 (6)0.0019 (7)
C30.0253 (8)0.0171 (10)0.0235 (9)0.0010 (6)0.0022 (6)0.0001 (7)
C40.0226 (8)0.0184 (10)0.0212 (8)0.0021 (6)0.0006 (6)0.0015 (7)
C50.0320 (9)0.0181 (10)0.0295 (10)0.0007 (7)0.0022 (7)0.0018 (7)
C60.0339 (10)0.0229 (10)0.0249 (9)0.0025 (7)0.0026 (7)0.0038 (8)
C70.0219 (9)0.0259 (11)0.0229 (9)0.0041 (6)0.0011 (6)0.0022 (7)
C80.0256 (9)0.0216 (10)0.0259 (9)0.0029 (6)0.0004 (7)0.0004 (7)
C90.0267 (9)0.0193 (10)0.0226 (8)0.0008 (6)0.0001 (6)0.0020 (7)
C100.0310 (10)0.0359 (13)0.0353 (11)0.0048 (8)0.0067 (8)0.0036 (9)
Geometric parameters (Å, º) top
O1—C11.223 (2)C4—C91.385 (2)
O2—C31.217 (2)C4—C51.403 (2)
O3—C71.370 (2)C5—C61.382 (2)
O3—C101.425 (2)C5—H50.9500
N1—C11.354 (2)C6—C71.388 (3)
N1—C31.406 (2)C6—H60.9500
N1—H10.911 (10)C7—C81.384 (2)
N2—C31.360 (2)C8—C91.397 (2)
N2—C41.420 (2)C8—H80.9500
N2—C21.460 (2)C9—H90.9500
C1—C21.506 (2)C10—H10A0.9800
C2—H2A0.9900C10—H10B0.9800
C2—H2B0.9900C10—H10C0.9800
C7—O3—C10116.85 (14)C6—C5—C4120.02 (17)
C1—N1—C3112.37 (14)C6—C5—H5120.0
C1—N1—H1122.9 (15)C4—C5—H5120.0
C3—N1—H1124.5 (15)C5—C6—C7120.87 (17)
C3—N2—C4126.92 (15)C5—C6—H6119.6
C3—N2—C2111.09 (14)C7—C6—H6119.6
C4—N2—C2121.66 (14)O3—C7—C8124.53 (17)
O1—C1—N1126.52 (17)O3—C7—C6115.84 (16)
O1—C1—C2126.75 (17)C8—C7—C6119.62 (16)
N1—C1—C2106.72 (15)C7—C8—C9119.67 (17)
N2—C2—C1102.84 (14)C7—C8—H8120.2
N2—C2—H2A111.2C9—C8—H8120.2
C1—C2—H2A111.2C4—C9—C8121.02 (16)
N2—C2—H2B111.2C4—C9—H9119.5
C1—C2—H2B111.2C8—C9—H9119.5
H2A—C2—H2B109.1O3—C10—H10A109.5
O2—C3—N2129.43 (17)O3—C10—H10B109.5
O2—C3—N1123.60 (16)H10A—C10—H10B109.5
N2—C3—N1106.95 (14)O3—C10—H10C109.5
C9—C4—C5118.78 (16)H10A—C10—H10C109.5
C9—C4—N2119.40 (15)H10B—C10—H10C109.5
C5—C4—N2121.82 (16)
C3—N1—C1—O1179.61 (16)C3—N2—C4—C50.8 (3)
C3—N1—C1—C20.94 (18)C2—N2—C4—C5173.66 (15)
C3—N2—C2—C11.19 (18)C9—C4—C5—C61.4 (2)
C4—N2—C2—C1175.05 (14)N2—C4—C5—C6178.85 (15)
O1—C1—C2—N2179.32 (16)C4—C5—C6—C70.3 (3)
N1—C1—C2—N20.13 (17)C10—O3—C7—C84.6 (2)
C4—N2—C3—O26.1 (3)C10—O3—C7—C6176.52 (15)
C2—N2—C3—O2179.53 (17)C5—C6—C7—O3178.02 (15)
C4—N2—C3—N1175.22 (14)C5—C6—C7—C80.9 (3)
C2—N2—C3—N11.77 (19)O3—C7—C8—C9177.92 (14)
C1—N1—C3—O2179.49 (15)C6—C7—C8—C90.9 (2)
C1—N1—C3—N21.71 (19)C5—C4—C9—C81.4 (3)
C3—N2—C4—C9179.43 (16)N2—C4—C9—C8178.85 (14)
C2—N2—C4—C96.6 (2)C7—C8—C9—C40.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.91 (1)1.95 (1)2.8512 (19)172 (2)
C2—H2A···O2ii0.992.343.291 (2)160
C8—H8···O2iii0.952.423.203 (2)140
Cg1···Cg1iv3.705 (3)
Cg1···Cg2v3.622 (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 formulaC10H10N2O3
Mr206.20
Crystal system, space groupMonoclinic, P21/c
Temperature (K)113
a, b, c (Å)4.9993 (10), 6.1566 (12), 30.052 (6)
β (°) 93.91 (3)
V3)922.8 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.24 × 0.12 × 0.10
Data collection
DiffractometerRigaku Saturn CCD area-detector
Absorption correctionMulti-scan
(CrystalClear; Rigaku/MSC, 2005)
Tmin, Tmax0.974, 0.989
No. of measured, independent and
observed [I > 2σ(I)] reflections
6955, 2203, 1507
Rint0.078
(sin θ/λ)max1)0.658
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.064, 0.151, 1.05
No. of reflections2203
No. of parameters142
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.44, 0.40

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

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.911 (10)1.946 (10)2.8512 (19)172 (2)
C2—H2A···O2ii0.992.343.291 (2)160
C8—H8···O2iii0.952.423.203 (2)140
Cg1···Cg1iv..3.705 (3).
Cg1···Cg2v..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

First citationGerdil, R. (1960). Acta Cryst. 13, 165–166.  CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
First citationKurzer, F., Arnold, R. T. & Krogh, L. C. (1963). Org. Synth. 4, 49.  Google Scholar
First citationNiwata, 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
First citationRigaku/MSC (2005). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890
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