1,3-Dicyclo-hexyl-imidazolidine-2,4,5-trione: a second polymorph.

The title compound, C(15)H(22)N(2)O(3), was obtained as a by-product of oxidative cleavage of 1,3-dicyclo-hexyl-(3-oxo-2,3-dihydro-benzofuran-2-yl)imidazolidine-2,4-dione. Herein, we report the crystal structure of a second polymorph, which was obtained by crystallization from an ethanol solution at 253 K, instead of slow evaporation of the same solvent at room temperature. While the first polymorph [Talhi et al. (2011). Acta Cryst. E67, o3243] crystallized in the non-centrosymmetric space group P2(1)2(1)2(1), this second polymorph crystallizes in the centrosymmetric space group P2(1)/n. Compared to the first polymorph, in the crystal no C=O⋯C=O inter-actions were found (C⋯O inter-molecular distance longer than 3.15 Å) and instead, close packing of individual mol-ecular units is mediated by C-H⋯π and weak C-H⋯O inter-actions.

Related literature

For the structure of the ortho­rhom­bic polymorph and further background information to the study, see: Talhi et al. (2011 ▶). For general background on crystallographic studies by our research group of related compounds having biological activity, see: Fernandes et al. (2011 ▶); Loughzail et al. (2011 ▶). For determination of the melting point, see: Ulrichan & Sayigh (1965 ▶).

Experimental

Crystal data

C15H22N2O3

M = 278.35

Monoclinic,

a = 5.1980 (2) Å

b = 21.7123 (10) Å

c = 13.0244 (6) Å

β = 100.163 (2)°

V = 1446.88 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 150 K

0.13 × 0.06 × 0.06 mm

Data collection

Bruker X8 Kappa CCD APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1998 ▶) T min = 0.989, T max = 0.995

38115 measured reflections

3876 independent reflections

2999 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.104

S = 1.04

3876 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.18 e Å−3

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

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812043619/nk2188sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812043619/nk2188Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812043619/nk2188Isup3.cdx

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812043619/nk2188Isup4.cml

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

C15H22N2O3	F(000) = 600
Mr = 278.35	Dx = 1.278 Mg m−3
Monoclinic, P21/n	Melting point: 175 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 5.1980 (2) Å	Cell parameters from 3876 reflections
b = 21.7123 (10) Å	θ = 3.7–29.1°
c = 13.0244 (6) Å	µ = 0.09 mm−1
β = 100.163 (2)°	T = 150 K
V = 1446.88 (11) Å3	Block, yellow
Z = 4	0.13 × 0.06 × 0.06 mm

Bruker X8 Kappa CCD APEXII diffractometer	3876 independent reflections
Radiation source: fine-focus sealed tube	2999 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
ω and φ scans	θmax = 29.1°, θmin = 3.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	h = −6→7
Tmin = 0.989, Tmax = 0.995	k = −29→29
38115 measured reflections	l = −17→17

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0374P)2 + 0.6588P] where P = (Fo2 + 2Fc2)/3
3876 reflections	(Δ/σ)max = 0.001
181 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

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
C1	0.9734 (2)	0.59882 (5)	0.12018 (9)	0.0179 (2)
C2	0.7011 (2)	0.59707 (6)	0.23971 (10)	0.0187 (2)
C3	0.6479 (2)	0.65531 (6)	0.17166 (10)	0.0189 (2)
C4	0.8265 (2)	0.69411 (5)	0.01391 (9)	0.0182 (2)
H4	0.9641	0.6788	−0.0245	0.022*
C5	0.9020 (3)	0.75914 (6)	0.05202 (10)	0.0225 (3)
H5A	1.0763	0.7585	0.0973	0.027*
H5B	0.7740	0.7748	0.0937	0.027*
C6	0.9077 (3)	0.80176 (6)	−0.04117 (11)	0.0246 (3)
H6A	0.9480	0.8442	−0.0157	0.030*
H6B	1.0482	0.7883	−0.0785	0.030*
C7	0.6476 (3)	0.80154 (6)	−0.11652 (10)	0.0224 (3)
H7A	0.5098	0.8190	−0.0815	0.027*
H7B	0.6613	0.8278	−0.1775	0.027*
C8	0.5724 (3)	0.73639 (6)	−0.15326 (10)	0.0255 (3)
H8A	0.7001	0.7208	−0.1951	0.031*
H8B	0.3982	0.7371	−0.1986	0.031*
C9	0.5654 (3)	0.69293 (6)	−0.06145 (10)	0.0235 (3)
H9A	0.4236	0.7056	−0.0242	0.028*
H9B	0.5282	0.6505	−0.0877	0.028*
C10	1.0256 (2)	0.50852 (5)	0.24346 (10)	0.0185 (2)
H10	1.1926	0.5048	0.2158	0.022*
C11	1.0949 (3)	0.50699 (6)	0.36255 (10)	0.0227 (3)
H11A	0.9339	0.5107	0.3929	0.027*
H11B	1.2105	0.5421	0.3876	0.027*
C12	1.2335 (3)	0.44639 (6)	0.39731 (11)	0.0257 (3)
H12A	1.4008	0.4443	0.3711	0.031*
H12B	1.2733	0.4448	0.4744	0.031*
C13	1.0635 (3)	0.39147 (6)	0.35622 (13)	0.0334 (3)
H13A	0.9026	0.3916	0.3871	0.040*
H13B	1.1593	0.3528	0.3773	0.040*
C14	0.9900 (3)	0.39390 (6)	0.23745 (13)	0.0351 (4)
H14A	0.8732	0.3589	0.2129	0.042*
H14B	1.1499	0.3897	0.2065	0.042*
C15	0.8525 (3)	0.45432 (6)	0.20050 (11)	0.0263 (3)
H15A	0.8176	0.4558	0.1233	0.032*
H15B	0.6832	0.4569	0.2251	0.032*
N1	0.9031 (2)	0.56747 (5)	0.20531 (8)	0.0185 (2)
N2	0.8172 (2)	0.65170 (5)	0.10196 (8)	0.0182 (2)
O1	1.13883 (18)	0.58316 (4)	0.07174 (7)	0.0244 (2)
O2	0.58424 (18)	0.58220 (4)	0.30792 (7)	0.0260 (2)
O3	0.49016 (18)	0.69488 (4)	0.18021 (8)	0.0259 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0198 (6)	0.0174 (5)	0.0157 (6)	−0.0008 (4)	0.0015 (5)	0.0002 (4)
C2	0.0183 (6)	0.0194 (5)	0.0182 (6)	−0.0008 (4)	0.0023 (5)	−0.0007 (4)
C3	0.0186 (6)	0.0201 (6)	0.0178 (6)	−0.0009 (5)	0.0025 (5)	0.0005 (5)
C4	0.0201 (6)	0.0183 (5)	0.0160 (6)	0.0007 (4)	0.0031 (5)	0.0049 (4)
C5	0.0232 (7)	0.0206 (6)	0.0215 (6)	−0.0030 (5)	−0.0022 (5)	0.0030 (5)
C6	0.0228 (7)	0.0216 (6)	0.0283 (7)	−0.0030 (5)	0.0012 (5)	0.0060 (5)
C7	0.0218 (6)	0.0223 (6)	0.0227 (6)	0.0025 (5)	0.0030 (5)	0.0060 (5)
C8	0.0282 (7)	0.0262 (6)	0.0198 (6)	−0.0003 (5)	−0.0019 (5)	0.0037 (5)
C9	0.0244 (7)	0.0227 (6)	0.0213 (6)	−0.0048 (5)	−0.0022 (5)	0.0024 (5)
C10	0.0209 (6)	0.0165 (5)	0.0182 (6)	0.0023 (4)	0.0041 (5)	0.0021 (4)
C11	0.0272 (7)	0.0213 (6)	0.0189 (6)	0.0027 (5)	0.0023 (5)	0.0016 (5)
C12	0.0277 (7)	0.0278 (6)	0.0210 (6)	0.0061 (5)	0.0026 (5)	0.0055 (5)
C13	0.0327 (8)	0.0228 (7)	0.0434 (9)	0.0033 (6)	0.0036 (7)	0.0134 (6)
C14	0.0391 (8)	0.0171 (6)	0.0442 (9)	0.0011 (6)	−0.0062 (7)	−0.0031 (6)
C15	0.0297 (7)	0.0187 (6)	0.0279 (7)	0.0001 (5)	−0.0025 (6)	−0.0008 (5)
N1	0.0214 (5)	0.0175 (5)	0.0176 (5)	0.0015 (4)	0.0059 (4)	0.0019 (4)
N2	0.0196 (5)	0.0176 (5)	0.0178 (5)	0.0020 (4)	0.0044 (4)	0.0027 (4)
O1	0.0287 (5)	0.0242 (4)	0.0225 (5)	0.0060 (4)	0.0105 (4)	0.0031 (4)
O2	0.0259 (5)	0.0288 (5)	0.0255 (5)	0.0017 (4)	0.0110 (4)	0.0057 (4)
O3	0.0251 (5)	0.0254 (5)	0.0284 (5)	0.0074 (4)	0.0079 (4)	0.0030 (4)

C1—O1	1.2017 (15)	C8—H8A	0.9900
C1—N2	1.4022 (15)	C8—H8B	0.9900
C1—N1	1.4033 (15)	C9—H9A	0.9900
C2—O2	1.2052 (15)	C9—H9B	0.9900
C2—N1	1.3723 (16)	C10—N1	1.4760 (15)
C2—C3	1.5409 (17)	C10—C15	1.5262 (17)
C3—O3	1.2062 (15)	C10—C11	1.5296 (17)
C3—N2	1.3734 (16)	C10—H10	1.0000
C4—N2	1.4781 (15)	C11—C12	1.5297 (18)
C4—C5	1.5250 (17)	C11—H11A	0.9900
C4—C9	1.5284 (18)	C11—H11B	0.9900
C4—H4	1.0000	C12—C13	1.524 (2)
C5—C6	1.5307 (18)	C12—H12A	0.9900
C5—H5A	0.9900	C12—H12B	0.9900
C5—H5B	0.9900	C13—C14	1.527 (2)
C6—C7	1.5239 (18)	C13—H13A	0.9900
C6—H6A	0.9900	C13—H13B	0.9900
C6—H6B	0.9900	C14—C15	1.5302 (19)
C7—C8	1.5220 (18)	C14—H14A	0.9900
C7—H7A	0.9900	C14—H14B	0.9900
C7—H7B	0.9900	C15—H15A	0.9900
C8—C9	1.5288 (18)	C15—H15B	0.9900
O1—C1—N2	126.12 (11)	H9A—C9—H9B	108.1
O1—C1—N1	126.00 (11)	N1—C10—C15	110.74 (10)
N2—C1—N1	107.88 (10)	N1—C10—C11	111.77 (10)
O2—C2—N1	129.00 (12)	C15—C10—C11	111.92 (10)
O2—C2—C3	125.55 (11)	N1—C10—H10	107.4
N1—C2—C3	105.45 (10)	C15—C10—H10	107.4
O3—C3—N2	128.81 (12)	C11—C10—H10	107.4
O3—C3—C2	125.96 (11)	C10—C11—C12	109.47 (10)
N2—C3—C2	105.22 (10)	C10—C11—H11A	109.8
N2—C4—C5	111.47 (10)	C12—C11—H11A	109.8
N2—C4—C9	109.93 (10)	C10—C11—H11B	109.8
C5—C4—C9	111.89 (10)	C12—C11—H11B	109.8
N2—C4—H4	107.8	H11A—C11—H11B	108.2
C5—C4—H4	107.8	C13—C12—C11	110.82 (11)
C9—C4—H4	107.8	C13—C12—H12A	109.5
C4—C5—C6	109.97 (10)	C11—C12—H12A	109.5
C4—C5—H5A	109.7	C13—C12—H12B	109.5
C6—C5—H5A	109.7	C11—C12—H12B	109.5
C4—C5—H5B	109.7	H12A—C12—H12B	108.1
C6—C5—H5B	109.7	C12—C13—C14	110.77 (12)
H5A—C5—H5B	108.2	C12—C13—H13A	109.5
C7—C6—C5	111.69 (11)	C14—C13—H13A	109.5
C7—C6—H6A	109.3	C12—C13—H13B	109.5
C5—C6—H6A	109.3	C14—C13—H13B	109.5
C7—C6—H6B	109.3	H13A—C13—H13B	108.1
C5—C6—H6B	109.3	C13—C14—C15	111.56 (12)
H6A—C6—H6B	107.9	C13—C14—H14A	109.3
C8—C7—C6	110.79 (11)	C15—C14—H14A	109.3
C8—C7—H7A	109.5	C13—C14—H14B	109.3
C6—C7—H7A	109.5	C15—C14—H14B	109.3
C8—C7—H7B	109.5	H14A—C14—H14B	108.0
C6—C7—H7B	109.5	C10—C15—C14	109.49 (11)
H7A—C7—H7B	108.1	C10—C15—H15A	109.8
C7—C8—C9	111.59 (11)	C14—C15—H15A	109.8
C7—C8—H8A	109.3	C10—C15—H15B	109.8
C9—C8—H8A	109.3	C14—C15—H15B	109.8
C7—C8—H8B	109.3	H15A—C15—H15B	108.2
C9—C8—H8B	109.3	C2—N1—C1	110.60 (10)
H8A—C8—H8B	108.0	C2—N1—C10	127.27 (10)
C4—C9—C8	110.55 (11)	C1—N1—C10	121.98 (10)
C4—C9—H9A	109.5	C3—N2—C1	110.76 (10)
C8—C9—H9A	109.5	C3—N2—C4	126.14 (10)
C4—C9—H9B	109.5	C1—N2—C4	122.96 (10)
C8—C9—H9B	109.5
O2—C2—C3—O3	3.1 (2)	O2—C2—N1—C10	1.1 (2)
N1—C2—C3—O3	−177.10 (12)	C3—C2—N1—C10	−178.71 (11)
O2—C2—C3—N2	−177.10 (12)	O1—C1—N1—C2	−177.91 (12)
N1—C2—C3—N2	2.67 (13)	N2—C1—N1—C2	2.28 (14)
N2—C4—C5—C6	−179.59 (10)	O1—C1—N1—C10	−1.95 (19)
C9—C4—C5—C6	−56.03 (14)	N2—C1—N1—C10	178.24 (10)
C4—C5—C6—C7	56.11 (15)	C15—C10—N1—C2	76.87 (15)
C5—C6—C7—C8	−56.18 (15)	C11—C10—N1—C2	−48.64 (16)
C6—C7—C8—C9	55.57 (15)	C15—C10—N1—C1	−98.38 (13)
N2—C4—C9—C8	−179.76 (10)	C11—C10—N1—C1	136.10 (12)
C5—C4—C9—C8	55.82 (14)	O3—C3—N2—C1	178.39 (13)
C7—C8—C9—C4	−55.24 (15)	C2—C3—N2—C1	−1.36 (13)
N1—C10—C11—C12	−177.09 (10)	O3—C3—N2—C4	−5.9 (2)
C15—C10—C11—C12	58.05 (14)	C2—C3—N2—C4	174.36 (11)
C10—C11—C12—C13	−57.32 (15)	O1—C1—N2—C3	179.78 (12)
C11—C12—C13—C14	57.00 (16)	N1—C1—N2—C3	−0.41 (14)
C12—C13—C14—C15	−56.42 (17)	O1—C1—N2—C4	3.89 (19)
N1—C10—C15—C14	177.51 (12)	N1—C1—N2—C4	−176.29 (10)
C11—C10—C15—C14	−57.06 (15)	C5—C4—N2—C3	64.30 (16)
C13—C14—C15—C10	55.77 (17)	C9—C4—N2—C3	−60.36 (15)
O2—C2—N1—C1	176.75 (13)	C5—C4—N2—C1	−120.46 (12)
C3—C2—N1—C1	−3.01 (13)	C9—C4—N2—C1	114.87 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7B···Cgi	0.99	2.78	3.5511 (14)	135
C11—H11B···O2ii	0.99	2.51	3.2065 (18)	127

Table 1

Short intermolecular interactions (Å, °)

Cg is the centroid of the N1/N2/C1–C3 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7B⋯Cg i	0.99	2.78	3.5511 (14)	135
C11—H11B⋯O2ii	0.99	2.51	3.2065 (18)	127

Symmetry codes: (i) ; (ii) .