1-(3-Chloro­phen­yl)-3-(4-nitro­phen­yl)urea

Ting Sun; Jing Li; Feng-Ling Yang

doi:10.1107/S1600536810040201

. 2010 Oct 13;66(Pt 11):o2812. doi: 10.1107/S1600536810040201

1-(3-Chlorophenyl)-3-(4-nitrophenyl)urea

Ting Sun ^a, Jing Li ^b, Feng-Ling Yang ^a,^*

PMCID: PMC3009072 PMID: 21589003

Abstract

In the title compound, C₁₃H₁₀ClN₃O₃, prepared by the reaction of 1-chloro-3-isocyanatobenzene with 4-nitrobenzenamine, the two substituent benzene rings are roughly coplanar [inter-ring dihedral angle = 8.70 (7)°]. In the crystal, molecules make cyclic intermolecular associations through two urea–nitro N—H⋯O hydrogen bonds, forming a chain structure [give chain direction] in which there are also weak intermolecular C—H⋯Cl interactions. The urea O atom has only intramolecular aromatic ring C—H⋯O associations.

Related literature

For the bioactivity of urea derivatives, see: Wang et al. (2001 ▶); Song et al. (2008 ▶); Yip et al. (1986 ▶); Liu et al. (2005 ▶).

Experimental

Crystal data

C₁₃H₁₀ClN₃O₃
M _r = 291.69
Monoclinic,
a = 8.3410 (13) Å
b = 12.5410 (18) Å
c = 12.1120 (16) Å
β = 99.866 (5)°
V = 1248.2 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 113 K
0.24 × 0.22 × 0.20 mm

Data collection

Rigaku Saturn724 CCD diffractometer
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2009 ▶) T _min = 0.928, T _max = 0.939
15672 measured reflections
2964 independent reflections
2396 reflections with I > 2σ(I)
R _int = 0.041

Refinement

R[F ² > 2σ(F ²)] = 0.033
wR(F ²) = 0.092
S = 1.04
2964 reflections
189 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: CrystalClear-SM Expert (Rigaku, 2009 ▶); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: CrystalStructure (Rigaku, 2009 ▶); software used to prepare material for publication: CrystalStructure.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810040201/zs2070sup1.cif

e-66-o2812-sup1.cif^{(17.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810040201/zs2070Isup2.hkl

e-66-o2812-Isup2.hkl^{(145.5KB, 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—H1⋯O3ⁱ	0.807 (16)	2.211 (16)	3.0131 (14)	172.8 (16)
N2—H2⋯O2ⁱ	0.832 (14)	2.136 (14)	2.9448 (14)	164.1 (14)
C3—H3⋯O1	0.95	2.26	2.8720 (15)	121
C9—H9⋯O1	0.95	2.31	2.8833 (15)	118
C12—H12⋯Cl1ⁱⁱ	0.95	2.83	3.5465 (13)	133

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

Acknowledgments

This work was supported by the Natural Science Foundation of Henan Province, China (grant No. 082300420110) and the Natural Science Foundation of Henan Province Education Department, China (grant No. 2007150036).

supplementary crystallographic information

Comment

Previous studies have shown that urea derivatives have important medical and biological applications, e.g. N, N'-diarylurea derivatives have cytokinin activity (Wang et al., 2001) and bacteriostatic activity. Compounds bearing a urea linkage to benzothiazole were also investigated for their ability to inhibit Raf-1 activity (Song et al.. 2008). Thidiazuron, a substituted heterocyclic urea compound, mimicked the effect of benzyladenine (BA) in the Ca²⁺ and cytokinin systems or on the IAA and cytokinin systems (Yip et al.. 1986). Recently, better activity was achieved with benzoyl urea derivatives (Liu et al.. 2005). In order to discover further biologically active urea compounds, the title compound C₁₃H₁₀ClN₃O₃ (I) was synthesized and its crystal structure is reported here.

In the structure of title compound (Fig. 1), the molecule is almost planar [torsion angles C1–N1–C2–C7 and C1–N2–C8–C13, 178.39 (11)° and -165.69 (11)°] with a dihedral angle between two phenyl rings of 8.70 (7)°. In the crystal structure, the molecules give cyclic intermolecular associations through two urea N–H···O_nitro hydrogen bonds (Table 1) giving a one-dimensional chain structure (Fig. 2) in which there are also weak intermolecular C—H···Cl interactions [C12–H12···Cl1ⁱⁱⁱ, 3.5465 (13) Å] [symmetry code (iii): x, y + 1, z]. The urea O atom has only intramolecular aromatic ring C–H···O associations [C3–H3···O1, 2.8720 (15) Å; C9–H9···O1, 2.8833 (15) Å].

Experimental

1-Chloro-3-isocyanatobenzene (0.153 g, 1 mmol) and 4-nitrobenzenamine (0.138 g, 1 mmol) were mixed and ground in an agate mortar, then irradiated by microwave for 1 min. After the reaction was completed, the resulting product was dissolved in 95% ethanol with warming and immediately filtered. The product obtained was recrystallized from ethanol and single crystals of the title compound were obtained by slow evaporation.