Bis[N-cyclohexyl-1-(2-{1-[(cyclohexyl­amino)carbonyl]cyclohexyl}-3,5-dioxo-1,2-oxazolidin-4-yl)cyclopentanecarbox­amide] monohydrate

Enayatollah Sheikhhosseini; Fahime Vafadarnejad; Azizollah Habibi

doi:10.1107/S1600536811028868

. 2011 Aug 2;67(Pt 9):o2239. doi: 10.1107/S1600536811028868

Bis[N-cyclohexyl-1-(2-{1-[(cyclohexylamino)carbonyl]cyclohexyl}-3,5-dioxo-1,2-oxazolidin-4-yl)cyclopentanecarboxamide] monohydrate

Enayatollah Sheikhhosseini ^a, Fahime Vafadarnejad ^b, Azizollah Habibi ^b,^*

PMCID: PMC3200895 PMID: 22058907

Abstract

The reaction of cyclohexyl isocyanide and alkylidene Meldrum’s acid (systematic name 2,2-dimethyl-1,3-dioxane-4,6-dione) in the presence of cyclohexyl ketoxime and dichloromethane as solvent resulted in the title compound, 2C₂₈H₄₃N₃O₅·H₂O. One methylene group of the cyclopentane ring was found to be disordered and was refined with occupancies 0.75:0.25. Intramolecular N—H⋯O hydrogen bonds occur. The crystal structure is stabilized by intermolecular N—H⋯O and O—H⋯O hydrogen bonds.

Related literature

For the biological activity of isoxazoles, see: Conti et al. (1998 ▶); Kang et al. (2000 ▶); Ko et al. (1998 ▶); Mishra et al. (1998 ▶).

Experimental

Crystal data

2C₂₈H₄₃N₃O₅·H₂O
M _r = 1021.32
Triclinic,
a = 11.3084 (6) Å
b = 12.3119 (7) Å
c = 20.7904 (11) Å
α = 102.686 (1)°
β = 103.104 (1)°
γ = 93.100 (1)°
V = 2733.9 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.60 × 0.50 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer
28848 measured reflections
11931 independent reflections
9099 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.120
S = 1.03
11931 reflections
675 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811028868/vm2097sup1.cif

e-67-o2239-sup1.cif^{(48KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811028868/vm2097Isup2.hkl

e-67-o2239-Isup2.hkl^{(583.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811028868/vm2097Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2A—H2AA⋯O5A	0.88	2.09	2.9371 (18)	161
N3A—H3AA⋯O1W	0.88	2.00	2.8662 (19)	170
N2B—H2BA⋯O5B	0.88	2.10	2.9330 (18)	157
N3B—H3BA⋯O3A	0.88	2.07	2.9238 (17)	163
O1W—H1WA⋯O4Bⁱ	0.85 (3)	1.90 (3)	2.7433 (18)	169 (2)
O1W—H1WB⋯O4Aⁱⁱ	0.89 (2)	1.88 (2)	2.7569 (18)	170 (2)

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Symmetry codes: (i) Inline graphic ; (ii) .

supplementary crystallographic information

Comment

Isoxazoles play an important role in heterocyclic chemistry and have served as versatile building blocks in organic synthesis. They have long been targeted in synthetic investigations for their known biological activities and pharmacological properties such as hypoglycemic, analgesic, anti-inflammatory and anti-bacterial activities (Conti et al., 1998; Mishra et al., 1998; Ko et al., 1998; Kang et al., 2000). The title compound was formed by reaction of cyclohexyl isocyanide and alkylidene Meldrum's acid in the presence of cyclohexyl ketoxime in dichloromethane as solvent. Fig. 1 shows the crystal structure of the title compound. The cyclohexyl and cyclopentyl rings have the normal shape (chair conformation for cyclohexyl and twisted envelope conformation for cyclopentyl ring), bond lengths and angles. Their planes align almost perpendicular in respect to the isoxazole core. The crystal structure is stabilized by N— H···O and O— H···O hydrogen bonds (Table 1, Fig. 2). Both molecules in the asymmetric unit interact by N3B—H3BA···O3A hydrogen bonding with D···A distance of 2.9238 (17) Å. There is also a N2B—H2BA···O5B intermolecular hydrogen bonding with D···A distance of 2.9330 (18) Å. The water molecule connects the molecules by N3A—H3AA···O1W, O1W—H1WA···O4B (-x + 1, -y + 2, -z + 1) and O1W—H1WB···O4A (x + 1, y, z) hydrogen bonds with D···A distances of 2.8662 (19), 2.7433 (18) and 2.7569 (18) Å respectively.

Experimental

The title compound was prepared by reaction of cyclohexyl isocyanide (4 mmol, 0.439 g) and alkylidene Meldrum's acid (2 mmol, 0.421 g) in the presence of cyclohexyl ketoxime (2 mmol, 0.226 g) in dichloromethane at room temperature within four hours. After evaporating the solvent, a white powder was separated from the reaction mixture.Crystallization and single-crystal preparation was done from an ethanol solution. Colorless crystals were obtained after two weeks at room temperature.