N,N′-Bis(4-fluoro­phen­yl)urea

Wan-Sin Loh; Hoong-Kun Fun; S Sarveswari; V Vijayakumar; R Venkat Ragavan

doi:10.1107/S1600536810016399

. 2010 May 12;66(Pt 6):o1319. doi: 10.1107/S1600536810016399

N,N′-Bis(4-fluorophenyl)urea

Wan-Sin Loh ^a,^‡, Hoong-Kun Fun ^a,^*,^§, S Sarveswari ^b, V Vijayakumar ^b, R Venkat Ragavan ^b

PMCID: PMC2979587 PMID: 21579412

Abstract

The asymmetric unit of the title compound, C₁₃H₁₀F₂N₂O, contains one and a half N,N′-bis(4-fluorophenyl)urea molecules. One of the molecules has crystallographic twofold rotation symmetry. The benzene rings are twisted from each other by dihedral angles of 29.69 (6)° for the molecule in a general position and 89.83 (6)° for the symmetry-generated molecule. In the crystal structure, a pair of intermolecular N—H⋯O hydrogen bonds link symmetry-related molecules into chains along the b axis, forming R ₂ ¹(6) ring motifs.

Related literature

For background to and the biological activity of bis-arylureas, see: Khire et al. (2004 ▶); McDonnell et al. (2008 ▶); Francisco et al. (2004 ▶); Bigi et al. (1998 ▶). For the synthetic method, see: Sarveswari & Raja (2006 ▶). For a related structure, see: Jai-nhuknan et al. (1997 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₁₃H₁₀F₂N₂O
M _r = 248.23
Monoclinic,
a = 67.541 (4) Å
b = 4.5750 (3) Å
c = 10.7098 (6) Å
β = 95.969 (2)°
V = 3291.4 (3) Å³
Z = 12
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 100 K
0.59 × 0.12 × 0.09 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.932, T _max = 0.990
21915 measured reflections
5986 independent reflections
4304 reflections with I > 2σ(I)
R _int = 0.050

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.159
S = 1.05
5986 reflections
257 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.69 e Å⁻³
Δρ_min = −0.51 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810016399/lh5040sup1.cif

e-66-o1319-sup1.cif^{(19.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810016399/lh5040Isup2.hkl

e-66-o1319-Isup2.hkl^{(293.1KB, 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
N1A—H1NA⋯O1Aⁱ	0.83 (2)	2.08 (2)	2.8331 (13)	151.7 (18)
N1B—H1NB⋯O1Bⁱ	0.89 (3)	2.02 (3)	2.8392 (18)	153.3 (19)
N2A—H2NA⋯O1Aⁱ	0.855 (18)	2.080 (17)	2.8547 (16)	150.5 (13)

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Symmetry code: (i) Inline graphic .

Acknowledgments

HKF and WSL thank Universiti Sains Malaysia (USM) for the Research University Golden Goose Grant (1001/PFIZIK/811012). WSL thanks the Malaysian Government and USM for the award of Research Fellowship. VV is grateful to the DST-India for funding through the Young Scientist Scheme (Fast Track Proposal).

supplementary crystallographic information

Comment

The synthesis of bis-arylureas has received considerable attention due to their wide range of biological applications. They act as potential Raf kinase inhibitors (Khire et al., 2004) and antagonists of human vanilloid receptor 1 (VR 1) (McDonnell et al., 2008). Phenyl thiazolylurea derivatives have been reported as inhibitors of Murine receptor A and Murine receptor B (Francisco et al., 2004). Some substituted ureas are used as antidiabetic and tranquilizing drugs, antioxidants in gasoline, corrosion inhibitor and herbicides (Bigi et al., 1998).

The asymmetric unit of the title compound (Fig. 1), comprises of one and a half N,N'-bis-(4-fluorophenyl)urea molecules. The half molecule has a twofold rotation symmetry, generated by symmetry code -x, y, -z+3/2. In the molecule with suffix A, both benzene rings (C1A–C6A and C8A–C13A) are twisted from each other with a dihedral angle of 29.69 (6)° whereas in molecule with suffix B, the dihedral angle between the benzene rings (C1B–C6B and C1BA–C6BA) is 89.83 (6)°. The structure is comparable to the related structure (Jai-nhuknan et al., 1997).

In the crystal packing (Fig. 2), intermolecular N1A—H1NA···O1A and N2A—H2NA···O1A hydrogen bonds (Table 1) link the adjacent molecules into chains along the b axis, forming R₂¹(6) ring motifs (Bernstein et al., 1995).

Experimental

The compound N,N'-bis-(4-fluorophenyl)urea was synthesized using the method available in the literature (Sarveswari & Raja, 2006) and the obtained crude product was recrystallized from absolute ethanol. M.P.: 519 K. Yield: 56%.