5-(4-Hy­droxy­phen­yl)imidazolidine-2,4-dione

Xue, J.; Qin, Y.; Zhang, Z.; Qiao, Y.

doi:10.1107/S1600536814010034

organic compounds

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COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 6| June 2014| Page o649

doi:10.1107/S1600536814010034

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5-(4-Hydroxyphenyl)imidazolidine-2,4-dione

Jin-hui Xue,^a Yong-qi Qin,^b Zi-feng Zhang ^a and Yuan-biao Qiao ^b ^*

^aDepartment of Chemistry and Chemical Engineering, Lvliang University, Lvliang, Shanxi 033001, People's Republic of China, and ^bLaboratory of Medicinal Chemistry, Lvliang University, Lvliang, Shanxi 033001, People's Republic of China
^*Correspondence e-mail: qinyq2003@163.com

Edited by V. Khrustalev, Russian Academy of Sciences, Russia (Received 10 April 2014; accepted 5 May 2014; online 10 May 2014)

The title compound, C₉H₈N₂O₃, was prepared by reaction of phenol, glyoxylic acid and urea in water. The imidazolidine ring adopts an almost planar conformation (r.m.s. deviation = 0.012 Å) and is twisted by 89.3 (1)° relative to the benzene ring. In the crystal, molecules are linked by N—H⋯O and O—H⋯O hydrogen bonds into a three-dimensional framework.

CCDC reference: 1000728

Related literature

For general background to the synthesis and applications of hydantoin derivatives, see: Liu & Zhao (2001 ); Dhar et al. (2002 ); Goodnow & Kang (2003 ). For related compounds, see: Ji et al. (2002 ).

Experimental

Crystal data

C₉H₈N₂O₃
M_r = 192.17
Monoclinic, P 2₁ /c
a = 10.3694 (11) Å
b = 6.9914 (8) Å
c = 12.3857 (13) Å
β = 105.619 (2)°
V = 864.76 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 296 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
4721 measured reflections
1558 independent reflections
1100 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.091
S = 1.02
1558 reflections
137 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O4ⁱ	0.883 (18)	1.952 (19)	2.8180 (19)	166.7 (17)
N1—H1⋯O4ⁱⁱ	0.85 (2)	2.535 (19)	3.204 (2)	136.5 (16)
N1—H1⋯O6ⁱⁱⁱ	0.85 (2)	2.36 (2)	3.067 (2)	141.1 (17)
O6—H6⋯O5^iv	0.95 (2)	1.78 (2)	2.7223 (18)	169.0 (18)
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) -x, -y, -z+1; (iv) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

CCDC reference: 1000728

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814010034/kq2013sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814010034/kq2013Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814010034/kq2013Isup3.cml

checkCIF report

Comment top

Hydantoin derivatives can be used as intermediates in pharmaceutical products, pesticides and photosensitive material. It is very important to the development of hydantoins compounds. Pharmacological functions of hydantoin derivatives are mainly shown in antibacterial (Liu & Zhao, 2001), diminishing inflammation (Dhar et al., 2002), relieving cough and asthma, lowering blood sugar (Goodnow & Kang, 2003), and inhibiting agent of uremic toxin. Different substituted hydantoin and its derivatives show good application future, such as the treatment of diabetes, kidney disease, autoimmune disease and blood disease. The spectrum of hydantoin derivatives is broad as bacterial disinfectant. They are widely used in aquaculture, pest and disease control, disinfection treatment of health equipment, mildew prevention and control of crops, preservation of vegetable & Fruit, and mildew anti-corrosion of industrial products and living goods.

In the molecule of the title compound, C₉H₈N₂O₃, I (Fig. 1) bond lengths and angles are generally normal (Ji et al., 2002). The imidazolidine ring adopts a planar conformation (r.m.s. deviation is 0.012 Å) and is twisted by 89.3 (1)° relative to the benzene plane.

In the crystal, molecules are bound by intermolecular N—H···O and O—H···O hydrogen bonds (Table 1) into three-dimensional framework (Fig. 2).

Related literature top

For general background to the synthesis and applications of hydantoin derivatives, see: Liu & Zhao (2001); Dhar et al. (2002); Goodnow & Kang (2003). For related compounds, see: Ji et al. (2002).

Experimental top

The title compound was prepared by reaction of phenol (0.05 mol), glyoxylic acid (0.06 mol) and urea (0.06 mol) in hydrochloric acid (37%, 80 ml) at 370 K for 6 h, cooling, filtering, affording the tile compound by recrystallization in water. Single crystals of the title compound suitable for X-ray measurements was obtained by recrystallization from ethanol at room temperature.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of I. Displacement ellipsoids are presented at the 40% probability level. H atoms are depicted as small spheres of arbitrary radius.
	Fig. 2. A portion of the crystal structure of I viewed along [001]. The intermolecular hydrogen bonding interactions are depicted by dashed lines.

5-(4-Hydroxyphenyl)imidazolidine-2,4-dione top

Crystal data top

C₉H₈N₂O₃	F(000) = 400
M_r = 192.17	D_x = 1.476 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.3694 (11) Å	Cell parameters from 933 reflections
b = 6.9914 (8) Å	θ = 2.0–25.0°
c = 12.3857 (13) Å	µ = 0.11 mm⁻¹
β = 105.619 (2)°	T = 296 K
V = 864.76 (16) Å³	Rectangle, colourless
Z = 4	0.30 × 0.20 × 0.20 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	1100 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.035
Graphite monochromator	θ_max = 25.2°, θ_min = 2.0°
phi and ω scans	h = −12→12
4721 measured reflections	k = −8→8
1558 independent reflections	l = −7→14

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.091	w = 1/[σ²(F_o²) + (0.0426P)² + 0.0206P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
1558 reflections	Δρ_max = 0.15 e Å⁻³
137 parameters	Δρ_min = −0.14 e Å⁻³
0 restraints	Extinction correction: SHELXL2013 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.024 (3)

Crystal data top

C₉H₈N₂O₃	V = 864.76 (16) Å³
M_r = 192.17	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.3694 (11) Å	µ = 0.11 mm⁻¹
b = 6.9914 (8) Å	T = 296 K
c = 12.3857 (13) Å	0.30 × 0.20 × 0.20 mm
β = 105.619 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	1100 reflections with I > 2σ(I)
4721 measured reflections	R_int = 0.035
1558 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.15 e Å⁻³
1558 reflections	Δρ_min = −0.14 e Å⁻³
137 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.

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

	x	y	z	U_iso*/U_eq
N1	0.36582 (16)	0.1852 (2)	0.60788 (13)	0.0438 (4)
H1	0.3651 (18)	0.070 (3)	0.6298 (15)	0.053*
N2	0.39496 (14)	0.4952 (2)	0.61795 (12)	0.0394 (4)
H2	0.4272 (18)	0.605 (3)	0.6494 (15)	0.047*
O4	0.46179 (12)	0.32043 (18)	0.78108 (10)	0.0464 (4)
O5	0.32237 (12)	0.58433 (19)	0.43383 (10)	0.0508 (4)
O6	−0.23743 (12)	0.1408 (2)	0.29172 (11)	0.0512 (4)
H6	−0.2595 (19)	0.108 (3)	0.2145 (17)	0.061*
C1	0.41256 (16)	0.3268 (3)	0.67946 (15)	0.0360 (4)
C2	0.34366 (16)	0.4631 (3)	0.50733 (15)	0.0362 (4)
C3	0.31532 (17)	0.2501 (2)	0.49270 (14)	0.0385 (5)
H3	0.3691	0.1943	0.4466	0.046*
C4	0.16868 (17)	0.2098 (2)	0.43983 (14)	0.0353 (4)
C5	0.07338 (17)	0.2567 (3)	0.49525 (15)	0.0410 (5)
H5	0.1009	0.3060	0.5676	0.049*
C6	−0.06081 (18)	0.2319 (3)	0.44558 (15)	0.0417 (5)
H6A	−0.1233	0.2633	0.4842	0.050*
C7	−0.10245 (17)	0.1601 (2)	0.33802 (14)	0.0366 (4)
C8	−0.00956 (17)	0.1091 (3)	0.28186 (14)	0.0413 (5)
H8	−0.0374	0.0583	0.2099	0.050*
C9	0.12569 (18)	0.1341 (3)	0.33336 (14)	0.0414 (5)
H9	0.1883	0.0992	0.2955	0.050*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0489 (10)	0.0338 (9)	0.0412 (10)	−0.0001 (8)	−0.0011 (7)	0.0047 (7)
N2	0.0423 (9)	0.0360 (9)	0.0336 (9)	−0.0046 (7)	−0.0009 (7)	0.0005 (7)
O4	0.0472 (8)	0.0544 (9)	0.0312 (8)	0.0075 (6)	−0.0002 (6)	0.0051 (6)
O5	0.0534 (9)	0.0547 (9)	0.0394 (8)	−0.0061 (7)	0.0038 (6)	0.0111 (7)
O6	0.0360 (8)	0.0701 (10)	0.0427 (8)	−0.0081 (6)	0.0023 (6)	−0.0054 (7)
C1	0.0277 (9)	0.0427 (11)	0.0348 (11)	0.0036 (8)	0.0035 (8)	0.0016 (8)
C2	0.0281 (9)	0.0437 (11)	0.0340 (11)	−0.0025 (8)	0.0036 (8)	0.0027 (9)
C3	0.0357 (10)	0.0431 (11)	0.0342 (10)	0.0011 (8)	0.0054 (8)	−0.0028 (8)
C4	0.0374 (10)	0.0326 (10)	0.0338 (10)	−0.0025 (8)	0.0063 (8)	−0.0021 (8)
C5	0.0433 (12)	0.0468 (11)	0.0310 (10)	−0.0035 (9)	0.0068 (8)	−0.0100 (8)
C6	0.0394 (11)	0.0483 (12)	0.0385 (11)	−0.0017 (9)	0.0126 (8)	−0.0076 (9)
C7	0.0330 (10)	0.0377 (11)	0.0359 (10)	−0.0036 (8)	0.0040 (8)	0.0007 (8)
C8	0.0460 (11)	0.0463 (11)	0.0297 (10)	−0.0078 (9)	0.0071 (8)	−0.0090 (8)
C9	0.0399 (11)	0.0489 (12)	0.0368 (11)	−0.0028 (9)	0.0124 (8)	−0.0078 (9)

Geometric parameters (Å, º) top

N1—C1	1.330 (2)	C3—H3	0.9800
N1—C3	1.454 (2)	C4—C9	1.379 (2)
N1—H1	0.85 (2)	C4—C5	1.386 (3)
N2—C2	1.348 (2)	C5—C6	1.373 (2)
N2—C1	1.387 (2)	C5—H5	0.9300
N2—H2	0.883 (18)	C6—C7	1.380 (2)
O4—C1	1.2251 (18)	C6—H6A	0.9300
O5—C2	1.220 (2)	C7—C8	1.378 (3)
O6—C7	1.3690 (19)	C8—C9	1.387 (2)
O6—H6	0.95 (2)	C8—H8	0.9300
C2—C3	1.519 (2)	C9—H9	0.9300
C3—C4	1.511 (2)

C1—N1—C3	113.08 (15)	C9—C4—C5	118.33 (16)
C1—N1—H1	121.6 (13)	C9—C4—C3	120.95 (17)
C3—N1—H1	125.3 (13)	C5—C4—C3	120.65 (16)
C2—N2—C1	111.98 (15)	C6—C5—C4	121.34 (17)
C2—N2—H2	126.3 (12)	C6—C5—H5	119.3
C1—N2—H2	121.0 (12)	C4—C5—H5	119.3
C7—O6—H6	112.8 (12)	C5—C6—C7	119.65 (17)
O4—C1—N1	129.33 (17)	C5—C6—H6A	120.2
O4—C1—N2	123.50 (17)	C7—C6—H6A	120.2
N1—C1—N2	107.17 (15)	O6—C7—C8	122.53 (16)
O5—C2—N2	125.82 (17)	O6—C7—C6	117.33 (16)
O5—C2—C3	127.01 (16)	C8—C7—C6	120.13 (15)
N2—C2—C3	107.16 (15)	C7—C8—C9	119.54 (16)
N1—C3—C4	114.94 (15)	C7—C8—H8	120.2
N1—C3—C2	100.48 (13)	C9—C8—H8	120.2
C4—C3—C2	111.97 (14)	C4—C9—C8	120.98 (17)
N1—C3—H3	109.7	C4—C9—H9	119.5
C4—C3—H3	109.7	C8—C9—H9	119.5
C2—C3—H3	109.7

C3—N1—C1—O4	−179.77 (17)	C2—C3—C4—C9	112.19 (19)
C3—N1—C1—N2	0.8 (2)	N1—C3—C4—C5	49.1 (2)
C2—N2—C1—O4	177.58 (16)	C2—C3—C4—C5	−64.7 (2)
C2—N2—C1—N1	−3.0 (2)	C9—C4—C5—C6	−1.0 (3)
C1—N2—C2—O5	−177.36 (17)	C3—C4—C5—C6	175.96 (17)
C1—N2—C2—C3	3.78 (19)	C4—C5—C6—C7	−0.5 (3)
C1—N1—C3—C4	−119.10 (17)	C5—C6—C7—O6	−179.04 (16)
C1—N1—C3—C2	1.27 (19)	C5—C6—C7—C8	1.6 (3)
O5—C2—C3—N1	178.20 (17)	O6—C7—C8—C9	179.43 (16)
N2—C2—C3—N1	−2.96 (17)	C6—C7—C8—C9	−1.3 (3)
O5—C2—C3—C4	−59.3 (2)	C5—C4—C9—C8	1.4 (3)
N2—C2—C3—C4	119.51 (16)	C3—C4—C9—C8	−175.60 (17)
N1—C3—C4—C9	−133.99 (17)	C7—C8—C9—C4	−0.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O4ⁱ	0.883 (18)	1.952 (19)	2.8180 (19)	166.7 (17)
N1—H1···O4ⁱⁱ	0.85 (2)	2.535 (19)	3.204 (2)	136.5 (16)
N1—H1···O6ⁱⁱⁱ	0.85 (2)	2.36 (2)	3.067 (2)	141.1 (17)
O6—H6···O5^iv	0.95 (2)	1.78 (2)	2.7223 (18)	169.0 (18)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O4ⁱ	0.883 (18)	1.952 (19)	2.8180 (19)	166.7 (17)
N1—H1···O4ⁱⁱ	0.85 (2)	2.535 (19)	3.204 (2)	136.5 (16)
N1—H1···O6ⁱⁱⁱ	0.85 (2)	2.36 (2)	3.067 (2)	141.1 (17)
O6—H6···O5^iv	0.95 (2)	1.78 (2)	2.7223 (18)	169.0 (18)

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

Acknowledgements

The authors thank the Colleges and Universities Technology Project of Shanxi Provine (20121033), and the Natural Science Fund of Lvliang University (contracts ZRXN201206 and ZRXN201210).

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dhar, T. G., Iwanowicz, E., Launay, M., Maillet, M., Nicolai, E. & Potin, D. (2002). Hydantoin compounds useful as anti-inflammatory agents. US Patent US2002/0143035A1[P]. Google Scholar
Goodnow, J. R. & Kang, L. (2003). Hydantoin-containing glucokinase activators. US Patent US2003/0225286A1[P]. Google Scholar
Ji, B. M., Du, C. X., Zhu, Y. & Wang, Y. (2002). Chin. J. Struct. Chem. 21, 252–255. CAS Google Scholar
Liu, J. & Zhao, Y. (2001). Chin. J. Disinfect. 18, 218–222. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar