1,3-Dicyclo-hexyl-imidazolidine-2,4,5-trione.

The title compound, C(15)H(22)N(2)O(3), has been isolated as a by-product of an oxidative cleavage of the C-C bond linking two five-membered rings of 1,3-dicyclo-hexyl-5-(3-oxo-2,3-dihydro-benzofuran-2-yl)imidazolidine-2,4-dione. Individual mol-ecular units are engaged in weak C=O⋯C=O inter-actions [O⋯C = 2.814 (10) and 2.871 (11) Å], leading to the formation of supra-molecular chains which close pack, mediated by van der Waals contacts, in the bc plane.

Related literature

For the synthesis of parabanic acid and its derivatives, see: Murray (1957 ▶, 1963 ▶); Ulrichan & Sayigh (1965 ▶); Richter et al. (1984 ▶); Orazi et al. (1977 ▶); Zarzyka-Niemiec & Lubczak (2004 ▶). For biological applications of parabanic acid and its derivatives, see: Ishii et al. (1991 ▶); Kotani et al. (1997 ▶); Sato et al. (2011 ▶). For the synthesis, characterization and biological studies of the title compound, see: Xia et al. (2011 ▶). For general background to crystallographic studies of compounds having biological activity from our research group, see: Fernandes et al. (2010 ▶, 2011 ▶); Loughzail et al. (2011 ▶). For the synthesis of a precursor mol­ecule, see: Talhi et al. (2011 ▶).

Experimental

Crystal data

C15H22N2O3

M = 278.35

Orthorhombic,

a = 6.5539 (8) Å

b = 11.5029 (15) Å

c = 19.524 (3) Å

V = 1471.9 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 150 K

0.05 × 0.03 × 0.02 mm

Data collection

Bruker X8 KappaCCD APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ▶) T min = 0.996, T max = 0.998

8292 measured reflections

1558 independent reflections

1028 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.106

wR(F 2) = 0.320

S = 1.06

1558 reflections

181 parameters

72 restraints

H-atom parameters constrained

Δρmax = 0.74 e Å−3

Δρmin = −0.42 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT-Plus (Bruker, 2005 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2009 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811046253/tk5010sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811046253/tk5010Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811046253/tk5010Isup3.cml

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

C15H22N2O3	F(000) = 600
Mr = 278.35	Dx = 1.256 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1312 reflections
a = 6.5539 (8) Å	θ = 2.7–19.0°
b = 11.5029 (15) Å	µ = 0.09 mm−1
c = 19.524 (3) Å	T = 150 K
V = 1471.9 (3) Å3	Block, yellow
Z = 4	0.05 × 0.03 × 0.02 mm

Bruker X8 KappaCCD APEXII diffractometer	1558 independent reflections
Radiation source: fine-focus sealed tube	1028 reflections with I > 2σ(I)
graphite	Rint = 0.047
ω and φ scans	θmax = 25.4°, θmin = 3.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −7→7
Tmin = 0.996, Tmax = 0.998	k = −13→10
8292 measured reflections	l = −23→23

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)] = 0.106	H-atom parameters constrained
wR(F2) = 0.320	w = 1/[σ2(Fo2) + (0.1747P)2 + 2.7021P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
1558 reflections	Δρmax = 0.74 e Å−3
181 parameters	Δρmin = −0.42 e Å−3
72 restraints	Absolute structure: nd
Primary atom site location: structure-invariant direct methods

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.

	x	y	z	Uiso*/Ueq
N1	0.2051 (11)	0.2826 (7)	0.6061 (4)	0.0494 (19)
N2	0.3789 (12)	0.4457 (7)	0.5865 (5)	0.061 (2)
O1	0.4234 (13)	0.3500 (10)	0.6889 (4)	0.103 (4)
O2	0.0437 (9)	0.2643 (6)	0.5014 (4)	0.0559 (17)
O3	0.2667 (13)	0.4828 (6)	0.4759 (4)	0.070 (2)
C1	0.3461 (15)	0.3562 (10)	0.6341 (5)	0.056 (3)
C2	0.1559 (11)	0.3133 (7)	0.5403 (4)	0.0366 (18)
C3	0.2743 (14)	0.4269 (7)	0.5262 (5)	0.046 (2)
C4	0.128 (2)	0.1759 (12)	0.6392 (7)	0.092 (4)
H4	0.0608	0.1463	0.5967	0.110*
C5	−0.0635 (16)	0.1903 (9)	0.6766 (5)	0.061 (3)
H5A	−0.1679	0.2213	0.6448	0.073*
H5B	−0.0430	0.2486	0.7133	0.073*
C6	−0.143 (2)	0.0794 (15)	0.7083 (7)	0.101 (4)
H6A	−0.1945	0.0989	0.7545	0.122*
H6B	−0.2615	0.0539	0.6808	0.122*
C7	−0.014 (3)	−0.0147 (13)	0.7150 (8)	0.107 (5)
H7A	−0.0962	−0.0843	0.7036	0.128*
H7B	0.0191	−0.0206	0.7644	0.128*
C8	0.1714 (19)	−0.0265 (11)	0.6797 (6)	0.075 (3)
H8A	0.1537	−0.0871	0.6442	0.091*
H8B	0.2753	−0.0552	0.7124	0.091*
C9	0.255 (2)	0.0814 (9)	0.6454 (6)	0.078 (3)
H9A	0.3775	0.1063	0.6712	0.094*
H9B	0.3010	0.0593	0.5989	0.094*
C10	0.5293 (19)	0.5375 (11)	0.5983 (8)	0.094 (4)
H10	0.5748	0.5134	0.6451	0.112*
C11	0.4542 (15)	0.6494 (8)	0.6151 (5)	0.054 (2)
H11A	0.3762	0.6429	0.6583	0.065*
H11B	0.3568	0.6729	0.5789	0.065*
C12	0.6092 (17)	0.7462 (9)	0.6235 (6)	0.066 (3)
H12A	0.5468	0.8193	0.6070	0.080*
H12B	0.6370	0.7559	0.6730	0.080*
C13	0.8030 (18)	0.7306 (10)	0.5885 (7)	0.080 (3)
H13A	0.7986	0.7795	0.5468	0.096*
H13B	0.9097	0.7639	0.6185	0.096*
C14	0.8732 (18)	0.6172 (11)	0.5677 (7)	0.083 (3)
H14A	0.9797	0.5925	0.6006	0.099*
H14B	0.9405	0.6258	0.5226	0.099*
C15	0.7265 (14)	0.5231 (8)	0.5621 (5)	0.050 (2)
H15A	0.7920	0.4513	0.5793	0.060*
H15B	0.6970	0.5109	0.5128	0.060*

	U11	U22	U33	U12	U13	U23
N1	0.034 (3)	0.061 (5)	0.054 (4)	0.001 (4)	0.008 (3)	0.011 (4)
N2	0.034 (4)	0.048 (5)	0.101 (6)	−0.008 (3)	−0.002 (4)	−0.043 (5)
O1	0.077 (5)	0.183 (10)	0.049 (4)	0.053 (6)	−0.018 (4)	−0.041 (5)
O2	0.043 (3)	0.048 (4)	0.077 (4)	0.003 (3)	−0.011 (3)	−0.021 (3)
O3	0.090 (5)	0.044 (4)	0.075 (4)	0.031 (4)	0.034 (4)	0.019 (3)
C1	0.041 (5)	0.072 (7)	0.056 (6)	0.014 (5)	−0.005 (5)	−0.020 (5)
C2	0.028 (4)	0.038 (4)	0.044 (4)	0.001 (3)	−0.007 (3)	−0.002 (3)
C3	0.046 (5)	0.027 (4)	0.063 (5)	0.008 (4)	0.007 (5)	−0.006 (4)
C4	0.061 (6)	0.097 (8)	0.118 (8)	0.019 (6)	0.030 (6)	0.053 (7)
C5	0.051 (5)	0.064 (6)	0.066 (5)	−0.007 (5)	0.015 (4)	−0.017 (5)
C6	0.067 (6)	0.137 (9)	0.100 (7)	−0.004 (7)	0.025 (6)	0.043 (7)
C7	0.120 (9)	0.078 (7)	0.122 (8)	−0.027 (7)	0.034 (8)	−0.003 (7)
C8	0.073 (6)	0.081 (7)	0.073 (6)	−0.014 (6)	−0.005 (5)	0.016 (5)
C9	0.079 (7)	0.052 (6)	0.103 (7)	−0.005 (6)	0.035 (6)	−0.007 (5)
C10	0.061 (6)	0.075 (7)	0.145 (9)	−0.023 (6)	0.017 (7)	−0.046 (7)
C11	0.049 (5)	0.043 (5)	0.071 (5)	−0.005 (4)	0.013 (4)	−0.003 (4)
C12	0.062 (6)	0.056 (6)	0.080 (6)	−0.016 (5)	0.011 (5)	−0.022 (5)
C13	0.070 (6)	0.054 (6)	0.117 (7)	−0.020 (5)	0.027 (6)	−0.001 (6)
C14	0.050 (5)	0.079 (7)	0.119 (7)	−0.012 (5)	0.016 (6)	−0.021 (6)
C15	0.037 (4)	0.051 (5)	0.061 (5)	0.005 (4)	0.005 (4)	−0.011 (4)

N1—C1	1.367 (12)	C8—C9	1.512 (16)
N1—C2	1.372 (10)	C8—H8A	0.9900
N1—C4	1.475 (14)	C8—H8B	0.9900
N2—C3	1.379 (12)	C9—H9A	0.9900
N2—C1	1.404 (14)	C9—H9B	0.9900
N2—C10	1.463 (13)	C10—C11	1.416 (15)
O1—C1	1.185 (11)	C10—C15	1.482 (15)
O2—C2	1.199 (10)	C10—H10	1.0000
O3—C3	1.176 (10)	C11—C12	1.516 (13)
C2—C3	1.544 (12)	C11—H11A	0.9900
C4—C9	1.373 (16)	C11—H11B	0.9900
C4—C5	1.464 (15)	C12—C13	1.453 (16)
C4—H4	1.0000	C12—H12A	0.9900
C5—C6	1.510 (18)	C12—H12B	0.9900
C5—H5A	0.9900	C13—C14	1.442 (16)
C5—H5B	0.9900	C13—H13A	0.9900
C6—C7	1.38 (2)	C13—H13B	0.9900
C6—H6A	0.9900	C14—C15	1.452 (14)
C6—H6B	0.9900	C14—H14A	0.9900
C7—C8	1.405 (19)	C14—H14B	0.9900
C7—H7A	0.9900	C15—H15A	0.9900
C7—H7B	0.9900	C15—H15B	0.9900
C1—N1—C2	111.9 (8)	H8A—C8—H8B	107.3
C1—N1—C4	124.8 (9)	C4—C9—C8	118.0 (10)
C2—N1—C4	123.0 (9)	C4—C9—H9A	107.8
C3—N2—C1	112.0 (7)	C8—C9—H9A	107.8
C3—N2—C10	125.6 (11)	C4—C9—H9B	107.8
C1—N2—C10	121.9 (10)	C8—C9—H9B	107.8
O1—C1—N1	127.8 (12)	H9A—C9—H9B	107.1
O1—C1—N2	125.2 (11)	C11—C10—N2	117.3 (10)
N1—C1—N2	107.0 (7)	C11—C10—C15	121.0 (10)
O2—C2—N1	128.1 (8)	N2—C10—C15	115.5 (9)
O2—C2—C3	126.5 (8)	C11—C10—H10	98.3
N1—C2—C3	105.5 (7)	N2—C10—H10	98.3
O3—C3—N2	130.5 (9)	C15—C10—H10	98.3
O3—C3—C2	126.1 (9)	C10—C11—C12	117.3 (9)
N2—C3—C2	103.3 (7)	C10—C11—H11A	108.0
C9—C4—C5	124.4 (10)	C12—C11—H11A	108.0
C9—C4—N1	119.4 (9)	C10—C11—H11B	108.0
C5—C4—N1	114.6 (10)	C12—C11—H11B	108.0
C9—C4—H4	94.1	H11A—C11—H11B	107.2
C5—C4—H4	94.1	C13—C12—C11	116.4 (9)
N1—C4—H4	94.1	C13—C12—H12A	108.2
C4—C5—C6	113.8 (10)	C11—C12—H12A	108.2
C4—C5—H5A	108.8	C13—C12—H12B	108.2
C6—C5—H5A	108.8	C11—C12—H12B	108.2
C4—C5—H5B	108.8	H12A—C12—H12B	107.3
C6—C5—H5B	108.8	C14—C13—C12	121.5 (9)
H5A—C5—H5B	107.7	C14—C13—H13A	106.9
C7—C6—C5	119.5 (11)	C12—C13—H13A	106.9
C7—C6—H6A	107.4	C14—C13—H13B	106.9
C5—C6—H6A	107.4	C12—C13—H13B	106.9
C7—C6—H6B	107.4	H13A—C13—H13B	106.7
C5—C6—H6B	107.4	C13—C14—C15	119.0 (9)
H6A—C6—H6B	107.0	C13—C14—H14A	107.6
C6—C7—C8	123.9 (13)	C15—C14—H14A	107.6
C6—C7—H7A	106.4	C13—C14—H14B	107.6
C8—C7—H7A	106.4	C15—C14—H14B	107.6
C6—C7—H7B	106.4	H14A—C14—H14B	107.0
C8—C7—H7B	106.4	C14—C15—C10	117.3 (8)
H7A—C7—H7B	106.4	C14—C15—H15A	108.0
C7—C8—C9	116.9 (12)	C10—C15—H15A	108.0
C7—C8—H8A	108.1	C14—C15—H15B	108.0
C9—C8—H8A	108.1	C10—C15—H15B	108.0
C7—C8—H8B	108.1	H15A—C15—H15B	107.2
C9—C8—H8B	108.1
C2—N1—C1—O1	−177.2 (9)	C1—N1—C4—C5	95.6 (13)
C4—N1—C1—O1	−2.9 (15)	C2—N1—C4—C5	−90.7 (13)
C2—N1—C1—N2	5.0 (10)	C9—C4—C5—C6	−16 (2)
C4—N1—C1—N2	179.4 (8)	N1—C4—C5—C6	178.3 (11)
C3—N2—C1—O1	177.6 (9)	C4—C5—C6—C7	16 (2)
C10—N2—C1—O1	5.2 (15)	C5—C6—C7—C8	−17 (3)
C3—N2—C1—N1	−4.6 (10)	C6—C7—C8—C9	14 (2)
C10—N2—C1—N1	−177.0 (8)	C5—C4—C9—C8	15 (2)
C1—N1—C2—O2	177.1 (8)	N1—C4—C9—C8	179.9 (11)
C4—N1—C2—O2	2.6 (13)	C7—C8—C9—C4	−12.7 (19)
C1—N1—C2—C3	−3.5 (9)	C3—N2—C10—C11	82.0 (15)
C4—N1—C2—C3	−178.0 (8)	C1—N2—C10—C11	−106.7 (14)
C1—N2—C3—O3	−179.9 (9)	C3—N2—C10—C15	−70.7 (15)
C10—N2—C3—O3	−7.8 (15)	C1—N2—C10—C15	100.6 (13)
C1—N2—C3—C2	2.4 (9)	N2—C10—C11—C12	−176.7 (11)
C10—N2—C3—C2	174.4 (9)	C15—C10—C11—C12	−25.6 (18)
O2—C2—C3—O3	2.2 (13)	C10—C11—C12—C13	23.8 (16)
N1—C2—C3—O3	−177.3 (9)	C11—C12—C13—C14	−20.9 (19)
O2—C2—C3—N2	−179.9 (8)	C12—C13—C14—C15	19 (2)
N1—C2—C3—N2	0.6 (8)	C13—C14—C15—C10	−19.0 (19)
C1—N1—C4—C9	−70.9 (17)	C11—C10—C15—C14	23.2 (19)
C2—N1—C4—C9	102.8 (14)	N2—C10—C15—C14	174.9 (11)