Crystal structure of 1-(2-amino­phen­yl)-3-phenyl­urea

Joel T Mague; Shaaban K Mohamed; Mehmet Akkurt; Omran A Omran; Mustafa R Albayati

doi:10.1107/S2056989014028175

. 2015 Jan 10;71(Pt 2):o88–o89. doi: 10.1107/S2056989014028175

Crystal structure of 1-(2-aminophenyl)-3-phenylurea

Joel T Mague ^a, Shaaban K Mohamed ^b,^c, Mehmet Akkurt ^d, Omran A Omran ^e, Mustafa R Albayati ^f,^*

PMCID: PMC4384537 PMID: 25878886

Abstract

In the title compound, C₁₃H₁₃N₃O, the phenyl ring makes a dihedral angle of 47.0 (1)° with the mean plane of the –NC(=O)N– unit, while the dihedral angle between the latter mean plane and the aminophenyl ring is 84.43 (7)°. In the crystal, molecules are linked via N—H⋯O hydrogen bonds involving the central –NHC(=O)NH– units, forming chains running parallel to the b axis. These chains associate with one another via N—H⋯O and N—H⋯N hydrogen bonds, from the pendant amino groups to the –NHC(=O)NH– units of adjacent molecules, forming columns propagating along [010]. The structure was refined as a two-component twin with a 0.933 (3):0.067 (3) domain ratio.

Keywords: crystal structure, urea derivatives, N—H⋯N hydrogen bonds, N—H⋯O hydrogen bonds, twinned structure

Related literature

For industrial applications of urea-containing compounds, see: Kapuscinska & Nowak (2014 ▸); Doyle & Jacobsen (2007 ▸); Helm et al. (1989 ▸). For the wide spectrum of biological activities of urea scaffold compounds, see: Upadhayaya et al. (2009 ▸); Khan et al. (2008 ▸), Seth et al. (2004 ▸); Kaymakçıoğlu et al. (2005 ▸); Yip & Yang (1986 ▸). For details of the use of the TWINROTMAT routine in PLATON, see: Spek (2009 ▸). graphic file with name e-71-00o88-scheme1.jpg

Experimental

Crystal data

C₁₃H₁₃N₃O
M _r = 227.26
Monoclinic,
a = 16.1742 (4) Å
b = 4.5667 (1) Å
c = 16.3259 (4) Å
β = 106.548 (1)°
V = 1155.93 (5) Å³
Z = 4
Cu Kα radiation
μ = 0.69 mm⁻¹
T = 150 K
0.20 × 0.12 × 0.09 mm

Data collection

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2014 ▸) T _min = 0.89, T _max = 0.94
21843 measured reflections
2282 independent reflections
2084 reflections with I > 2σ(I)
R _int = 0.035

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.136
S = 1.11
2282 reflections
155 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: APEX2 (Bruker, 2014 ▸); cell refinement: SAINT (Bruker, 2014 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXT (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008 ▸); molecular graphics: DIAMOND (Brandenburg & Putz, 2012 ▸); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▸) and PLATON (Spek, 2009 ▸).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989014028175/su5051sup1.cif

e-71-00o88-sup1.cif^{(640.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989014028175/su5051Isup2.hkl

e-71-00o88-Isup2.hkl^{(125.5KB, hkl)}

Click here for additional data file.^{(4.6KB, cml)}

Supporting information file. DOI: 10.1107/S2056989014028175/su5051Isup3.cml

Click here for additional data file.^{(1.2MB, tif)}

. DOI: 10.1107/S2056989014028175/su5051fig1.tif

The molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

Click here for additional data file.^{(1.3MB, tif)}

c . DOI: 10.1107/S2056989014028175/su5051fig2.tif

A view along the c axis of the crystal packing of the title compound. The N—H⋯O and N—H⋯N hydrogen bonds are shown by blue and violet dashed lines, respectively (see Table 1 for details).

CCDC reference: 1041048

Additional supporting information: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (, ).

DHA	DH	HA	D A	DHA
N2H2AO1ⁱ	0.91	2.13	2.932(2)	147
N1H1AO1ⁱ	0.91	1.94	2.771(2)	151
N3H3AN3ⁱⁱ	0.91	2.19	3.057(3)	160
N3H3BO1ⁱⁱ	0.91	2.24	3.004(2)	141

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

Acknowledgments

The support of NSF–MRI grant No. 1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged.

supplementary crystallographic information

S1. Comment

Compounds bearing a urea linkage have attracted the interest of many researchers due to the variety of their applications in both of medicinal and industrial fields. One of the most important class of compounds that are used in the cosmetic industry are urea-containing compounds due to their effective moisturizing properties (Kapuscinska & Nowak, 2014). Urea-linked glycosides serve as small-molecule H-bond donors in asymmetric catalysis (Doyle & Jacobsen, 2007), and are currently employed in the forestry product industry, for example as adhesive mixtures to reduce the level of toxic phenol in furniture and building materials (Helm et al., 1989). Some urea derivatives possess valuable antituberculosis, antibacterial and anticonvulsant properties (Upadhayaya et al., 2009; Khan et al., 2008, Sett et al., 2004; Koçyiğit-Kaymakçıoğlu et al., 2005). Compounds such as Thidiazuron have mimicked the effect of benzyladenine (BA) in the Ca²⁺ and cytokinin systems (Yip et al., 1986). Based on such findings we report in this study the synthesis and crystal structure of the title compound.

The phenyl ring makes a dihedral angle of 47.0 (1)° with the mean plane of atoms N1/N2/C7/O1 while the dihedral angle between the latter unit and the aminophenyl ring is 84.43 (7)°.

In the crystal, N1—H1A···O1ⁱ and N2—H2a···O1ⁱ hydrogen bonds link chains of molecules running parallel to the b axis (Fig. 2 and Table 1). Pairs of chains are further associated through N3—H3A···N3ⁱⁱ and N3—H3B···O1ⁱⁱ hydrogen bonds (Table 1 and Fig. 2), forming columns propagating along [010].

S2. Experimental

A mixture of 0.01 mol (2.06 g m) of N-phenylmorpholine-4-carboxamide and 0.01 mol (1.08 g m) benzene-1,2-diamine in 20 ml of ethanol was heated under reflux for 10 h. On cooling, the resulting solid product was collected by filtration, washed with a little cold ethanol and dried under vacuum. Colourless crystals suitable for X-ray diffraction were obtained by recrystallization of the product from ethanol (m.p.: 495 K; yield: 73%).