5-Isopropyl-imidazolidine-2,4-dione monohydrate.

In the title compound, C(6)H(10)N(2)O(2)·H(2)O, the imidazole ring is essentially planar, with a maximum deviation of 0.012 (2) Å. In the crystal, mol-ecules are connected via N-H⋯O and O-H⋯O hydrogen bonds, forming a supra-molecular tape along the a axis.

Related literature

For details and applications of hydantoins, see: El-Deeb et al. (2010 ▶); Rajic et al. (2006 ▶); Carmi et al. (2006 ▶); Sergent et al., (2008 ▶); Yu et al. (2004 ▶). For related structues, see: Delgado et al. (2007 ▶); Ciechanowicz-Rutkowska et al. (1994 ▶). For the synthetic procedure, see: Abdel-Aziz (2007 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C6H10N2O2·H2O

M = 160.18

Orthorhombic,

a = 6.2688 (3) Å

b = 9.2387 (4) Å

c = 14.8280 (7) Å

V = 858.77 (7) Å3

Z = 4

Cu Kα radiation

μ = 0.84 mm−1

T = 296 K

0.90 × 0.21 × 0.16 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.518, T max = 0.879

5702 measured reflections

1497 independent reflections

1378 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.098

S = 1.09

1497 reflections

117 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.12 e Å−3

Δρmin = −0.18 e Å−3

Absolute structure: Flack (1983 ▶), with 592 Friedel pairs

Flack parameter: 0.2 (3)

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812002838/is5056sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812002838/is5056Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812002838/is5056Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C6H10N2O2·H2O	F(000) = 344
Mr = 160.18	Dx = 1.239 Mg m−3
Orthorhombic, P212121	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2281 reflections
a = 6.2688 (3) Å	θ = 5.6–65.9°
b = 9.2387 (4) Å	µ = 0.84 mm−1
c = 14.8280 (7) Å	T = 296 K
V = 858.77 (7) Å3	Needle, colourless
Z = 4	0.90 × 0.21 × 0.16 mm

Bruker SMART APEXII CCD area-detector diffractometer	1497 independent reflections
Radiation source: fine-focus sealed tube	1378 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ and ω scans	θmax = 67.3°, θmin = 5.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −7→5
Tmin = 0.518, Tmax = 0.879	k = −11→10
5702 measured reflections	l = −17→17

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)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.098	w = 1/[σ2(Fo2) + (0.0552P)2 + 0.0813P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max = 0.001
1497 reflections	Δρmax = 0.12 e Å−3
117 parameters	Δρmin = −0.18 e Å−3
0 restraints	Absolute structure: Flack (1983), 592 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.2 (3)

Experimental. 1H NMR (DMSO–d6): 10.54 (s, 1H, NH), 7.87 (s, 1H, NH), 3.89 (s, 1H), 2.01–1.97 (m, 1H), 0.94–0.92 (d, 3H, J = 7.0 Hz), 0.80–0.78 (d, 3H, J = 6.5 Hz). 13C NMR (DMSO–d6): 175.87, 158.28, 63.22, 30.01, 18.93, 16.31.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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.

	x	y	z	Uiso*/Ueq
O1	0.6583 (2)	0.56794 (15)	0.46328 (11)	0.0679 (5)
O2	1.2150 (2)	0.27203 (15)	0.39487 (11)	0.0590 (4)
N1	0.6703 (3)	0.34173 (17)	0.39871 (11)	0.0472 (4)
N2	0.9719 (2)	0.44507 (16)	0.43611 (11)	0.0503 (4)
C1	0.7524 (3)	0.46070 (19)	0.43523 (13)	0.0481 (4)
C2	1.0337 (3)	0.31526 (19)	0.40226 (13)	0.0440 (4)
C3	0.8324 (3)	0.23514 (18)	0.37618 (12)	0.0436 (4)
H3A	0.8156	0.1507	0.4156	0.052*
C4	0.8317 (3)	0.1851 (2)	0.27789 (14)	0.0534 (5)
H4A	0.9533	0.1196	0.2701	0.064*
C5	0.6312 (4)	0.0986 (3)	0.25796 (19)	0.0828 (8)
H5A	0.6202	0.0197	0.2998	0.124*
H5B	0.6381	0.0613	0.1976	0.124*
H5C	0.5086	0.1602	0.2639	0.124*
C6	0.8624 (5)	0.3102 (3)	0.21256 (16)	0.0810 (7)
H6A	0.9926	0.3600	0.2266	0.122*
H6B	0.7446	0.3760	0.2177	0.122*
H6C	0.8694	0.2736	0.1520	0.122*
H1N1	0.543 (4)	0.329 (2)	0.3981 (13)	0.045 (5)*
H1N2	1.059 (5)	0.509 (3)	0.4591 (17)	0.078 (8)*
O1W	0.2489 (3)	0.63212 (17)	0.52044 (13)	0.0665 (4)
H1W1	0.374 (6)	0.617 (3)	0.507 (2)	0.096 (11)*
H2W2	0.214 (6)	0.721 (4)	0.531 (3)	0.122 (13)*

	U11	U22	U33	U12	U13	U23
O1	0.0438 (9)	0.0566 (8)	0.1033 (12)	0.0068 (6)	−0.0017 (7)	−0.0302 (8)
O2	0.0292 (8)	0.0607 (8)	0.0871 (11)	0.0039 (6)	−0.0030 (6)	−0.0086 (7)
N1	0.0246 (8)	0.0507 (8)	0.0662 (10)	−0.0020 (6)	−0.0013 (6)	−0.0127 (7)
N2	0.0309 (9)	0.0475 (8)	0.0725 (11)	−0.0035 (6)	−0.0045 (7)	−0.0147 (8)
C1	0.0372 (10)	0.0474 (9)	0.0597 (12)	0.0028 (8)	−0.0024 (8)	−0.0079 (8)
C2	0.0312 (9)	0.0468 (9)	0.0541 (10)	−0.0018 (7)	−0.0011 (7)	−0.0001 (8)
C3	0.0323 (9)	0.0394 (8)	0.0591 (10)	−0.0025 (6)	0.0003 (7)	−0.0028 (7)
C4	0.0443 (11)	0.0491 (9)	0.0667 (12)	−0.0016 (8)	0.0028 (8)	−0.0161 (8)
C5	0.0645 (16)	0.0895 (17)	0.0945 (18)	−0.0206 (13)	−0.0049 (14)	−0.0376 (14)
C6	0.098 (2)	0.0838 (16)	0.0617 (14)	−0.0079 (15)	0.0041 (13)	−0.0044 (12)
O1W	0.0438 (10)	0.0557 (8)	0.1000 (12)	−0.0042 (7)	−0.0067 (8)	−0.0203 (8)

O1—C1	1.226 (2)	C4—C5	1.518 (3)
O2—C2	1.210 (2)	C4—C6	1.520 (3)
N1—C1	1.329 (2)	C4—H4A	0.9800
N1—C3	1.454 (2)	C5—H5A	0.9600
N1—H1N1	0.80 (2)	C5—H5B	0.9600
N2—C2	1.357 (2)	C5—H5C	0.9600
N2—C1	1.383 (3)	C6—H6A	0.9600
N2—H1N2	0.87 (3)	C6—H6B	0.9600
C2—C3	1.513 (2)	C6—H6C	0.9600
C3—C4	1.529 (3)	O1W—H1W1	0.82 (4)
C3—H3A	0.9800	O1W—H2W2	0.87 (4)
C1—N1—C3	112.51 (15)	C5—C4—C3	110.30 (17)
C1—N1—H1N1	120.6 (15)	C6—C4—C3	112.16 (16)
C3—N1—H1N1	126.2 (15)	C5—C4—H4A	107.2
C2—N2—C1	111.89 (15)	C6—C4—H4A	107.2
C2—N2—H1N2	124.4 (19)	C3—C4—H4A	107.2
C1—N2—H1N2	123.6 (19)	C4—C5—H5A	109.5
O1—C1—N1	128.32 (19)	C4—C5—H5B	109.5
O1—C1—N2	124.05 (17)	H5A—C5—H5B	109.5
N1—C1—N2	107.63 (16)	C4—C5—H5C	109.5
O2—C2—N2	126.42 (17)	H5A—C5—H5C	109.5
O2—C2—C3	126.79 (16)	H5B—C5—H5C	109.5
N2—C2—C3	106.79 (15)	C4—C6—H6A	109.5
N1—C3—C2	101.12 (13)	C4—C6—H6B	109.5
N1—C3—C4	114.95 (15)	H6A—C6—H6B	109.5
C2—C3—C4	113.19 (15)	C4—C6—H6C	109.5
N1—C3—H3A	109.1	H6A—C6—H6C	109.5
C2—C3—H3A	109.1	H6B—C6—H6C	109.5
C4—C3—H3A	109.1	H1W1—O1W—H2W2	116 (3)
C5—C4—C6	112.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O2i	0.81 (2)	2.12 (2)	2.927 (2)	174.0 (19)
N2—H1N2···O1Wii	0.87 (3)	1.88 (3)	2.751 (2)	173 (2)
O1W—H1W1···O1	0.82 (4)	1.95 (4)	2.767 (2)	173 (3)
O1W—H2W2···O1iii	0.86 (4)	1.98 (4)	2.839 (2)	171 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O2i	0.81 (2)	2.12 (2)	2.927 (2)	174.0 (19)
N2—H1N2⋯O1Wii	0.87 (3)	1.88 (3)	2.751 (2)	173 (2)
O1W—H1W1⋯O1	0.82 (4)	1.95 (4)	2.767 (2)	173 (3)
O1W—H2W2⋯O1iii	0.86 (4)	1.98 (4)	2.839 (2)	171 (4)

Symmetry codes: (i) ; (ii) ; (iii) .