1,3-Dicyclo­hexyl-1-(4-nitro­benzo­yl)urea

A N Dhinaa; R Jagan; K Sivakumar; K Chinnakali

doi:10.1107/S1600536810016107

. 2010 May 8;66(Pt 6):o1291. doi: 10.1107/S1600536810016107

1,3-Dicyclohexyl-1-(4-nitrobenzoyl)urea

A N Dhinaa ^a, R Jagan ^a, K Sivakumar ^a, K Chinnakali ^a,^*

PMCID: PMC2979486 PMID: 21579388

Abstract

In the title compound, C₂₀H₂₇N₃O₄, both cyclohexane rings adopt chair conformations. The benzene ring and the amide group are oriented at a dihedral angle of 62.1 (2)°. In the crystal structure, intermolecular N—H⋯O and C—H⋯O hydrogen bonds link the molecules into chains propagating in [010], which contain R ₂ ²(12) ring motifs.

Related literature

For the biological activity of benzoylurea and N-aroylurea derivatives, see: Song et al. (2008 ▶, 2009 ▶); Amornraksa et al. (2009 ▶). For related N-benzoyl-N,N′-dicyclohexylurea structures, see: Orea Flores et al. (2006 ▶); Wang & Peng (2008 ▶).

Experimental

Crystal data

C₂₀H₂₇N₃O₄
M _r = 373.45
Monoclinic,
a = 25.294 (2) Å
b = 9.5757 (7) Å
c = 16.6943 (14) Å
β = 105.140 (2)°
V = 3903.1 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 292 K
0.25 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker 1999 ▶) T _min = 0.836, T _max = 0.982
22623 measured reflections
5012 independent reflections
3152 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.138
S = 1.02
5012 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810016107/hb5432sup1.cif

e-66-o1291-sup1.cif^{(21.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810016107/hb5432Isup2.hkl

e-66-o1291-Isup2.hkl^{(245.6KB, 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
N1—H1A⋯O1ⁱ	0.86	2.10	2.9396 (15)	166
C1—H1⋯O2ⁱⁱ	0.98	2.43	3.3636 (18)	160

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

Acknowledgments

The authors thank Dr Babu Varghese, SAIF, IIT-Madras, Chennai, for providing data-collection facilities.

supplementary crystallographic information

Comment

Benzoylurea derivatives act as antimitotic (Song et al., 2008) and antiproliferative (Song et al., 2009) agents. Some of the N-aroylurea analogs have been found to exhibit antioxidant activity (Amornraksa et al., 2009). We report here the crystal structure of the title compound, (I), an aroylurea.

In the title molecule (Fig. 1), both cyclohexane rings adopt chair conformations. The benzoyl carbonyl group is twisted away from the N–H group and as a result no intramolecular N—H···O hydrogen bond is formed. The dihedral angle between the N1/C7/O1 and N2/C14/O2 planes is 65.0 (2)°. The amide group (C7/O1/N1) and the benzene ring (C15–C20) are oriented at a dihedral angle of 62.1 (1)°. The nitro group is almost coplanar with the attached benzene ring [C19—C18—N3—O3 = -0.8 (3)° and C17—C18—N3—O4 = -1.6 (3)°]. Bond lengths and angles are comparable to those observed in N-benzoyl-N,N'-dicyclohexylurea (Orea Flores et al., 2006) and N-(4-bromobenzoyl)-N,N-dicyclohexylurea (Wang & Peng, 2008).

In the crystal structure, N1—H1A···O1ⁱ and C1—H1···O2ⁱⁱ hydrogen bonds (symmetry codes as in Table 1) generate R²₂(12) ring motifs which are fused into a ribbon-like structure along the b axis (Fig.2).

Experimental

4-Nitrobenzoic acid (1 g, 5.9 mmol) and dicyclohexylcarbodiimide (1.203 g, 5.9 mmol) were dissolved in dichloromethane (30 ml). The resulting mixture was stirred overnight and then the solvent was removed by rotary evaporator. The product was isolated by column chromatography by using ethyl acetate-hexane (1:9) as eluent. Pale yellow blocks of (I) were obtained by slow evaporation of an ethanolic solution over a period of two weeks.