N-(4-Bromo­benzo­yl)-N,N′-dicyclo­hexyl­urea

Ya-Wen Wang; Yu Peng

doi:10.1107/S1600536807064756

. 2007 Dec 6;64(Pt 1):o160. doi: 10.1107/S1600536807064756

N-(4-Bromobenzoyl)-N,N′-dicyclohexylurea

Ya-Wen Wang ^a, Yu Peng ^a,^*

PMCID: PMC2915228 PMID: 21200726

Abstract

In the title compound, C₂₀H₂₇BrN₂O₂, molecules are linked into one-dimensional chains through (amide)N—H⋯O=C(amide) intermolecular hydrogen bonds.

Related literature

For related literature, see: Bohne et al. (2005 ▶); Bondy et al. (2004 ▶); Bruker (2000 ▶); Ślebioda (1995 ▶). For literature on related crystal structures, see: Ball et al. (1990 ▶); Chérioux et al. (2002 ▶); Gallagher et al. (1999 ▶); Govindasamy & Subramanian (1997 ▶); Toniolo et al. (1990 ▶); Wu et al. (2006 ▶).

Experimental

Crystal data

C₂₀H₂₇BrN₂O₂
M _r = 407.35
Monoclinic,
a = 13.501 (2) Å
b = 9.5621 (10) Å
c = 16.306 (2) Å
β = 114.443 (6)°
V = 1916.3 (4) Å³
Z = 4
Mo Kα radiation
μ = 2.16 mm⁻¹
T = 113 (2) K
0.38 × 0.16 × 0.14 mm

Data collection

Rigaku Saturn CCD diffractometer
Absorption correction: multi-scan (REQABS; Jacobson, 1998 ▶) T _min = 0.484, T _max = 0.739
17461 measured reflections
4526 independent reflections
3651 reflections with I > 2σ(I)
R _int = 0.044

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.078
S = 1.06
4526 reflections
231 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Data collection: CrystalClear (Jacobson, 1999 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: CrystalStructure (Rigaku, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807064756/pk2071sup1.cif

e-64-0o160-sup1.cif^{(20.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807064756/pk2071Isup2.hkl

e-64-0o160-Isup2.hkl^{(221.8KB, 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
N2—H2A⋯O2ⁱ	0.898 (10)	2.072 (11)	2.961 (2)	170 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors acknowledge financial support from the Research Fund for New Faculty at the State Key Laboratory of Applied Organic Chemistry.

supplementary crystallographic information

Comment

The first conscious total synthesis of a natural product was that of urea in 1828 by Wohler, which marks the beginnings of organic synthesis. Since then, many urea derivatives have been prepared and have demonstrated a wide range of uses, including fluorescence probes (Bohne et al., 2005) and anion receptors (Bondy et al., 2004).

The title compound, an N-acylurea derivative, can be conveniently prepared from dicyclohexylcarbodiimide (DCC) and p-bromobenzoic acid according to reported methods (Ślebioda, 1995). The molecular structure is shown in Fig.1. Each cyclohexyl group adopts the chair conformation, as is required for energy minimization. The two carbonyl groups are twisted substantially at the central atom, N1, with a dihedral angle of 66.43 (10)° between the O1/C7/N1 and O2/C14/N2 planes, which increases the distance between atoms O1 and N2. As a result, no intramolecular N2–H2A···O1 hydrogen bond is formed. However, molecules are linked into chains through (amide) N–H···O=C (amide) intermolecular hydrogen bonds, reinforced by C–H···O=C interactions. Surprisingly, this supramolecular arrangement is not observed in a closely related X-ray structure (Gallagher et al., 1999).

Experimental

p-bromobenzoic acid (201 mg, 1 mmol) was dissolved in CHCl₃ (5 ml) and DCC (206 mg, 1 mmol) and N,N-dimethylpyridin-4-amine (122 mg, 1 mmol) were added to the solution. The resulting mixture was stirred for 1 h at 298 K. After evaporation of the solvent, a colorless solid was isolated. Single crystals suitable for X-ray structure determination were obtained by slow evaporation of a EtOAc solution over a period of several days.