3-Hy­droxy­methyl-1-(4-meth­oxy­phen­yl)imidazolidine-2,4-dione

Cheng, X.-C.; Hou, J.-J.; Wang, R.-L.; Dong, W.-L.

doi:10.1107/S1600536810026838

organic compounds

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ISSN: 2056-9890

Volume 66| Part 8| August 2010| Page o2027

https://doi.org/10.1107/S1600536810026838

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3-Hydroxymethyl-1-(4-methoxyphenyl)imidazolidine-2,4-dione

Xian-Chao Cheng,^a Jing-Jing Hou,^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 4 July 2010; accepted 7 July 2010; online 14 July 2010)

In the title molecule, C₁₁H₁₂N₂O₄, the dihedral angle between the benzene ring and imidazolidine ring is 7.1 (5)°. In the crystal structure, the hydroxy groups are involved in the formation of intermolecular O—H⋯O hydrogen bonds, which link the molecules related by translation into C(2) chains along the b axis.

Related literature

For related structures, see: Gerdil (1960 ); Sun et al. (2010 ). For details of the synthesis, see Niwata et al. (1997 ).

Experimental

Crystal data

C₁₁H₁₂N₂O₄
M_r = 236.23
Monoclinic, P 2₁ /c
a = 21.280 (4) Å
b = 6.3309 (13) Å
c = 7.8813 (16) Å
β = 100.52 (3)°
V = 1043.9 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 113 K
0.20 × 0.18 × 0.12 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.977, T_max = 0.986
7503 measured reflections
1841 independent reflections
1540 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.112
S = 1.09
1841 reflections
156 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O4ⁱ	0.82	1.92	2.7346 (17)	174
Symmetry code: (i) x, y+1, z.

Data collection: CrystalClear (Rigaku, 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/S1600536810026838/cv2742sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810026838/cv2742Isup2.hkl

checkCIF report

Comment top

During the research of novel antidiabetic agents, we found that imidazolidine-2,4-dione derivatives had potent antidiabetic activities. The crystal structure of the title compound was determined to investigate the relationship between structure and antidiabetic activity.

In the title compound, all bond lengths and angles are normal and in a good agreement with those reported previously (Gerdil, 1960; Sun et al., 2010). The dihedral angle between the benzene ring (C2—C7) and imidazolidine ring (C9—C10/N1/N2) is 7.1 (5)°. In the crystal structure, the hydroxy groups are involved in formaton of intermolecular O—H···O hydrogen bonds (Table 1), which link the molecules related by translation along axis b into linear chains.

Related literature top

For related structures, see: Gerdil (1960); Sun et al. (2010). For details of the synthesis, see Niwata et al. (1997).

Experimental top

A mixture of 1-(4-methoxyphenyl)imidazolidine-2,4-dione (0.27 g, 1.32 mmol), 37% formaldehyde (2.1 ml, 27.9 mmol), and methanol (8 ml) was stirred at 70 ° C for 2 h. After the reaction, water (8 ml) was added and the precipitate was filtered and washed with water to give 3-(hydroxymethyl)-1-(4-methoxyphenyl)imidazolidine-2,4-dione (0.27 g, 90% yield) (Niwata et al., 1997). Crystals suitable for X-ray diffraction were obtained through slow evaporation of a solution of the pure title compound in dichloromethane/methanol (1/1 by volume).

Structure description top

For related structures, see: Gerdil (1960); Sun et al. (2010). For details of the synthesis, see Niwata et al. (1997).

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 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, with displacement ellipsoids drawn at the 40% probability level.

3-Hydroxymethyl-1-(4-methoxyphenyl)imidazolidine-2,4-dione top

Crystal data top

C₁₁H₁₂N₂O₄	F(000) = 496
M_r = 236.23	D_x = 1.503 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2988 reflections
a = 21.280 (4) Å	θ = 2.0–27.9°
b = 6.3309 (13) Å	µ = 0.12 mm⁻¹
c = 7.8813 (16) Å	T = 113 K
β = 100.52 (3)°	Platelet, colorless
V = 1043.9 (4) Å³	0.20 × 0.18 × 0.12 mm
Z = 4

Data collection top

Rigaku Saturn CCD area-detector diffractometer	1841 independent reflections
Radiation source: rotating anode	1540 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.042
Detector resolution: 7.31 pixels mm^-1	θ_max = 25.0°, θ_min = 2.0°
ω and φ scans	h = −25→23
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −7→7
T_min = 0.977, T_max = 0.986	l = −7→9
7503 measured reflections

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0696P)² + 0.0281P] where P = (F_o² + 2F_c²)/3
1841 reflections	(Δ/σ)_max < 0.001
156 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₁H₁₂N₂O₄	V = 1043.9 (4) Å³
M_r = 236.23	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 21.280 (4) Å	µ = 0.12 mm⁻¹
b = 6.3309 (13) Å	T = 113 K
c = 7.8813 (16) Å	0.20 × 0.18 × 0.12 mm
β = 100.52 (3)°

Data collection top

Rigaku Saturn CCD area-detector diffractometer	1841 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	1540 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.986	R_int = 0.042
7503 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.112	H-atom parameters constrained
S = 1.09	Δρ_max = 0.18 e Å⁻³
1841 reflections	Δρ_min = −0.23 e Å⁻³
156 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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	0.06206 (5)	0.43299 (18)	0.14946 (13)	0.0262 (3)
O2	0.31479 (5)	0.92240 (17)	0.56402 (13)	0.0239 (3)
O3	0.41891 (6)	0.98695 (18)	0.93286 (14)	0.0310 (3)
H3	0.4247	1.1116	0.9119	0.046*
O4	0.43355 (5)	0.41010 (18)	0.88227 (13)	0.0263 (3)
N1	0.29378 (6)	0.5666 (2)	0.60155 (15)	0.0189 (3)
N2	0.38408 (6)	0.7058 (2)	0.74760 (15)	0.0198 (3)
C1	0.02888 (8)	0.2377 (3)	0.1525 (2)	0.0333 (4)
H1A	0.0536	0.1259	0.1151	0.050*
H1B	−0.0118	0.2463	0.0767	0.050*
H1C	0.0225	0.2095	0.2679	0.050*
C2	0.11895 (7)	0.4547 (3)	0.26381 (19)	0.0207 (4)
C3	0.14827 (7)	0.6511 (3)	0.26585 (19)	0.0229 (4)
H3A	0.1292	0.7568	0.1921	0.027*
C4	0.20547 (7)	0.6918 (3)	0.37598 (19)	0.0216 (4)
H4	0.2243	0.8244	0.3768	0.026*
C5	0.23490 (7)	0.5332 (3)	0.48603 (18)	0.0188 (4)
C6	0.20577 (7)	0.3369 (3)	0.48223 (18)	0.0208 (4)
H6	0.2252	0.2302	0.5544	0.025*
C7	0.14802 (7)	0.2966 (3)	0.3726 (2)	0.0234 (4)
H7	0.1290	0.1644	0.3722	0.028*
C8	0.32780 (7)	0.7496 (2)	0.62781 (19)	0.0188 (4)
C9	0.38857 (7)	0.4969 (3)	0.78904 (18)	0.0208 (4)
C10	0.32821 (7)	0.3927 (3)	0.69862 (18)	0.0208 (4)
H10A	0.3374	0.2813	0.6222	0.025*
H10B	0.3041	0.3342	0.7807	0.025*
C11	0.43450 (7)	0.8604 (3)	0.79990 (19)	0.0237 (4)
H11A	0.4748	0.7887	0.8400	0.028*
H11B	0.4392	0.9482	0.7021	0.028*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0191 (6)	0.0278 (7)	0.0292 (6)	−0.0026 (5)	−0.0022 (5)	−0.0004 (5)
O2	0.0255 (6)	0.0176 (6)	0.0282 (6)	−0.0021 (5)	0.0038 (5)	0.0026 (5)
O3	0.0468 (8)	0.0223 (7)	0.0258 (6)	−0.0109 (6)	0.0117 (5)	−0.0066 (5)
O4	0.0242 (6)	0.0259 (7)	0.0264 (6)	0.0028 (5)	−0.0021 (5)	−0.0016 (5)
N1	0.0182 (7)	0.0165 (7)	0.0207 (7)	−0.0004 (5)	0.0000 (5)	0.0008 (5)
N2	0.0198 (7)	0.0196 (7)	0.0196 (7)	−0.0036 (5)	0.0026 (5)	−0.0025 (5)
C1	0.0251 (9)	0.0371 (11)	0.0347 (9)	−0.0111 (8)	−0.0024 (7)	0.0010 (8)
C2	0.0170 (8)	0.0262 (9)	0.0189 (8)	0.0003 (6)	0.0029 (6)	−0.0035 (7)
C3	0.0215 (8)	0.0233 (9)	0.0234 (8)	0.0019 (7)	0.0028 (6)	0.0033 (7)
C4	0.0213 (8)	0.0189 (8)	0.0247 (8)	−0.0008 (6)	0.0046 (6)	0.0014 (7)
C5	0.0180 (8)	0.0214 (8)	0.0175 (8)	−0.0004 (6)	0.0048 (6)	−0.0021 (6)
C6	0.0207 (8)	0.0195 (9)	0.0216 (8)	0.0005 (6)	0.0024 (6)	0.0019 (6)
C7	0.0231 (8)	0.0208 (9)	0.0262 (8)	−0.0049 (7)	0.0040 (6)	−0.0017 (7)
C8	0.0188 (8)	0.0205 (8)	0.0182 (8)	−0.0021 (6)	0.0063 (6)	−0.0023 (6)
C9	0.0224 (8)	0.0222 (9)	0.0182 (8)	0.0012 (7)	0.0049 (6)	−0.0027 (6)
C10	0.0222 (8)	0.0181 (8)	0.0211 (8)	0.0004 (6)	0.0017 (6)	−0.0001 (6)
C11	0.0206 (8)	0.0267 (9)	0.0235 (8)	−0.0069 (7)	0.0032 (6)	−0.0034 (7)

Geometric parameters (Å, º) top

O1—C2	1.3778 (18)	C2—C7	1.388 (2)
O1—C1	1.426 (2)	C2—C3	1.390 (2)
O2—C8	1.2147 (19)	C3—C4	1.384 (2)
O3—C11	1.406 (2)	C3—H3A	0.9300
O3—H3	0.8200	C4—C5	1.398 (2)
O4—C9	1.2252 (19)	C4—H4	0.9300
N1—C8	1.3614 (19)	C5—C6	1.387 (2)
N1—C5	1.4238 (19)	C6—C7	1.391 (2)
N1—C10	1.460 (2)	C6—H6	0.9300
N2—C9	1.361 (2)	C7—H7	0.9300
N2—C8	1.411 (2)	C9—C10	1.503 (2)
N2—C11	1.4556 (19)	C10—H10A	0.9700
C1—H1A	0.9600	C10—H10B	0.9700
C1—H1B	0.9600	C11—H11A	0.9700
C1—H1C	0.9600	C11—H11B	0.9700

C2—O1—C1	117.01 (13)	C4—C5—N1	122.16 (14)
C11—O3—H3	109.5	C5—C6—C7	121.23 (15)
C8—N1—C5	127.24 (13)	C5—C6—H6	119.4
C8—N1—C10	111.11 (12)	C7—C6—H6	119.4
C5—N1—C10	121.46 (13)	C2—C7—C6	119.68 (15)
C9—N2—C8	111.44 (12)	C2—C7—H7	120.2
C9—N2—C11	124.73 (13)	C6—C7—H7	120.2
C8—N2—C11	123.31 (13)	O2—C8—N1	128.95 (14)
O1—C1—H1A	109.5	O2—C8—N2	123.76 (14)
O1—C1—H1B	109.5	N1—C8—N2	107.30 (13)
H1A—C1—H1B	109.5	O4—C9—N2	126.35 (15)
O1—C1—H1C	109.5	O4—C9—C10	126.42 (16)
H1A—C1—H1C	109.5	N2—C9—C10	107.23 (12)
H1B—C1—H1C	109.5	N1—C10—C9	102.77 (13)
O1—C2—C7	124.84 (15)	N1—C10—H10A	111.2
O1—C2—C3	115.85 (14)	C9—C10—H10A	111.2
C7—C2—C3	119.31 (15)	N1—C10—H10B	111.2
C4—C3—C2	121.01 (15)	C9—C10—H10B	111.2
C4—C3—H3A	119.5	H10A—C10—H10B	109.1
C2—C3—H3A	119.5	O3—C11—N2	109.40 (12)
C3—C4—C5	119.91 (15)	O3—C11—H11A	109.8
C3—C4—H4	120.0	N2—C11—H11A	109.8
C5—C4—H4	120.0	O3—C11—H11B	109.8
C6—C5—C4	118.84 (14)	N2—C11—H11B	109.8
C6—C5—N1	119.00 (14)	H11A—C11—H11B	108.2

C1—O1—C2—C7	4.5 (2)	C10—N1—C8—O2	177.46 (15)
C1—O1—C2—C3	−176.06 (14)	C5—N1—C8—N2	−177.40 (13)
O1—C2—C3—C4	179.71 (13)	C10—N1—C8—N2	−2.44 (17)
C7—C2—C3—C4	−0.8 (2)	C9—N2—C8—O2	−175.85 (14)
C2—C3—C4—C5	0.7 (2)	C11—N2—C8—O2	−3.8 (2)
C3—C4—C5—C6	0.0 (2)	C9—N2—C8—N1	4.06 (17)
C3—C4—C5—N1	179.89 (14)	C11—N2—C8—N1	176.11 (12)
C8—N1—C5—C6	−177.26 (14)	C8—N2—C9—O4	175.87 (14)
C10—N1—C5—C6	8.2 (2)	C11—N2—C9—O4	4.0 (2)
C8—N1—C5—C4	2.8 (2)	C8—N2—C9—C10	−3.93 (17)
C10—N1—C5—C4	−171.66 (14)	C11—N2—C9—C10	−175.84 (12)
C4—C5—C6—C7	−0.5 (2)	C8—N1—C10—C9	0.15 (15)
N1—C5—C6—C7	179.56 (14)	C5—N1—C10—C9	175.45 (13)
O1—C2—C7—C6	179.69 (13)	O4—C9—C10—N1	−177.52 (15)
C3—C2—C7—C6	0.2 (2)	N2—C9—C10—N1	2.27 (15)
C5—C6—C7—C2	0.4 (2)	C9—N2—C11—O3	−105.04 (16)
C5—N1—C8—O2	2.5 (3)	C8—N2—C11—O3	83.98 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O4ⁱ	0.82	1.92	2.7346 (17)	174

Symmetry code: (i) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₂N₂O₄
M_r	236.23
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	113
a, b, c (Å)	21.280 (4), 6.3309 (13), 7.8813 (16)
β (°)	100.52 (3)
V (Å³)	1043.9 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.20 × 0.18 × 0.12

Data collection
Diffractometer	Rigaku Saturn CCD area-detector
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.977, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	7503, 1841, 1540
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.112, 1.09
No. of reflections	1841
No. of parameters	156
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.23

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O4ⁱ	0.82	1.92	2.7346 (17)	174.0

Symmetry code: (i) x, y+1, z.

Acknowledgements

This research was supported by the National Natural Science Foundation of China (grant No. 20972112), the Key Program of Tianjin Natural Science Foundation (grant No. 09JCZDJC21600), the Specialized Research Fund for the Doctoral Program of Higher Education of China (grant No. 20091202110010) and the Tianjin Medical University Science Foundation (grant No. 2009ky16).

References

Gerdil, R. (1960). Acta Cryst. 13, 165–166. CSD CrossRef CAS IUCr Journals Web of Science 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. (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sun, S.-X., Zhang, H., Cheng, X.-C., Wang, R.-L. & Dong, W.-L. (2010). Acta Cryst. E66, o1308. Web of Science CSD CrossRef IUCr Journals Google Scholar