1,3-Dicyclo­hexyl-1-isonicotinoylurea monohydrate

Cun-Kuan Wang; Feng-Yan Zhou

doi:10.1107/S1600536808019430

. 2008 Jul 9;64(Pt 8):o1451. doi: 10.1107/S1600536808019430

1,3-Dicyclohexyl-1-isonicotinoylurea monohydrate

Cun-Kuan Wang ^a,^*, Feng-Yan Zhou ^b

PMCID: PMC2962082 PMID: 21203166

Abstract

The title organic compound, C₁₉H₂₇N₃O₂·H₂O, was synthesized from methylene dicyclohexylamine, 4-pyridinecarboxylic acid and N,N′-dicyclohexylcarbodiimide. The water molecule is involved in intermolecular hydrogen bonds, linking symmetry-related urea molecules into a two-dimensional supramolecular ladder-like structure.

Related literature

For related literature, see: Iyer et al. (1971 ▶); Jew et al. (2003 ▶); Li et al. (2006 ▶); Mu & Qin (2003 ▶); Wachter et al. (1998 ▶).

Experimental

Crystal data

C₁₉H₂₇N₃O₂·H₂O
M _r = 347.45
Triclinic,
a = 6.6694 (13) Å
b = 11.106 (2) Å
c = 13.248 (3) Å
α = 98.55 (3)°
β = 94.11 (3)°
γ = 97.49 (3)°
V = 958.0 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 (2) K
0.40 × 0.33 × 0.28 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.968, T _max = 0.977
9385 measured reflections
4284 independent reflections
2948 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.119
S = 1.04
4284 reflections
342 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: APEX2 (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); 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 datablocks global, I. DOI: 10.1107/S1600536808019430/cs2080sup1.cif

e-64-o1451-sup1.cif^{(20.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808019430/cs2080Isup2.hkl

e-64-o1451-Isup2.hkl^{(209.9KB, hkl)}

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
O3—H6⋯O1	0.89 (3)	1.95 (3)	2.7959 (18)	158 (2)
N2—H10⋯O3ⁱ	0.91 (2)	1.89 (2)	2.7949 (19)	170 (2)
O3—H12⋯O2ⁱⁱ	0.89 (2)	1.95 (3)	2.8319 (19)	171 (2)

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

Acknowledgments

The authors are grateful to the K. C. Wong Magna Fund of Ningbo University.

supplementary crystallographic information

Comment

Pyridine derivatives are important intermediates widely used in the synthesis of drugs (Wachter et al., 1998; Jew et al., 2003) and pesticides (Li et al., 2006; Mu & Qin, 2003). The title organic compound, 1,3-dicyclohexyl-1-isonicotinoyl-urea, is an intermediate for the synthesis of an anti-tuberculosis drug (Iyer et al., 1971). We report here its synthesis and the crystal structure of its hydrate.

The title compound was synthesized from methylene dicyclohexylamine, 4-pyridinecarboxylic acid and N,N'-dicyclohexylcarbodiimide. Asymmetric unit of the crystal structure consists of the organic molecule and one H₂O molecule, C₁₉H₂₇N₃O₂.H₂O. As shown in Fig. 1 and Table 1, the cyclohexyl groups display chair-type conformation. Interestingly, there are some strong intermolecular hydrogen bonds between the organic molecules and the crystal water. Thus each water effectively links two molecules as O–H···O donor to their O=C groups and accepts one N–H···O hydrogen bridge from a third molecule into a novel two-dimensional supramolecular ladder-like structure through both O—H···O and N—H···O hydrogen bonds (Fig.2 and Table 2).

Experimental

Methylene dicyclohexylamine (0.21 g, 1 mmol), 4-pyridinecarboxylic acid (0.12 g, 1 mmol) and N,N'-dicyclohexylcarbodiimide (0.25 g, 1.2 mmol) were added to a 50 ml round bottom flask, then added dichloromethane (25 ml). The mixture was stirred for 12 h at 298 K, after that the reaction mixture was washed with water (10 ml × 3). The organic layer was dried with anhydrous Na₂SO₄ and evaporated in vacuo to give a residue. The crude product was purified by column chromatography (SiO₂–EtOAc and hexane, 1:10) to afford the title compound as a colorless solid (yield 69%). ¹H NMR (400 MHz, CDCl₃): d 8.57 (d, J = 5.6 Hz, 2 H), 7.37 (d, J = 5.6 Hz, 2 H), 4.16–4.11 (m, 1 H), 3.27–3.22 (m, 1 H), 1.81–1.64 (m, 8 H), 1.60–1.57 (m, 2 H), 1.51–1.22 (m, 4 H), 1.17–1.08 (m, 2 H), 1.00–0.94 (m, 2 H), 0.85–0.76 (m, 2 H).