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

Mague, J.T.; Mohamed, S.K.; Akkurt, M.; Omran, O.A.; Albayati, M.R.

doi:10.1107/S2056989014028175

organic compounds

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ISSN: 2056-9890

Volume 71| Part 2| February 2015| Pages o88-o89

doi:10.1107/S2056989014028175

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

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

^aDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, ^bChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, ^cChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, ^dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^eChemistry Department, Faculty of Science, Sohag University, 82524 Sohag, Egypt, and ^fKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
^*Correspondence e-mail: shaabankamel@yahoo.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 21 December 2014; accepted 26 December 2014; online 10 January 2015)

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.

CCDC reference: 1041048

1. 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 ).

2. Experimental

2.1. Crystal data

C₁₃H₁₃N₃O
M_r = 227.26
Monoclinic, P 2₁ /n
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

2.2. 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

2.3. Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1ⁱ	0.91	2.13	2.932 (2)	147
N1—H1A⋯O1ⁱ	0.91	1.94	2.771 (2)	151
N3—H3A⋯N3ⁱⁱ	0.91	2.19	3.057 (3)	160
N3—H3B⋯O1ⁱⁱ	0.91	2.24	3.004 (2)	141
Symmetry codes: (i) x, y-1, z; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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).

Supporting information

CCDC reference: 1041048

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2056989014028175/su5051sup1.cif

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

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

checkCIF report

Comment top

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].

Related literature top

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).

Experimental top

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%).

Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); 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).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. 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).

1-(2-Aminophenyl)-3-phenylurea top

Crystal data top

C₁₃H₁₃N₃O	F(000) = 480
M_r = 227.26	D_x = 1.306 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54178 Å
a = 16.1742 (4) Å	Cell parameters from 9955 reflections
b = 4.5667 (1) Å	θ = 3.4–72.4°
c = 16.3259 (4) Å	µ = 0.69 mm⁻¹
β = 106.548 (1)°	T = 150 K
V = 1155.93 (5) Å³	Column, colourless
Z = 4	0.20 × 0.12 × 0.09 mm

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	2282 independent reflections
Radiation source: INCOATEC IµS micro–focus source	2084 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.035
Detector resolution: 10.4167 pixels mm^-1	θ_max = 72.5°, θ_min = 2.8°
ω scans	h = −19→17
Absorption correction: multi-scan (SADABS; Bruker, 2014)	k = −5→5
T_min = 0.89, T_max = 0.94	l = −20→20
21843 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.049	Hydrogen site location: mixed
wR(F²) = 0.136	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.054P)² + 0.8485P] where P = (F_o² + 2F_c²)/3
2282 reflections	(Δ/σ)_max < 0.001
155 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₃H₁₃N₃O	V = 1155.93 (5) Å³
M_r = 227.26	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 16.1742 (4) Å	µ = 0.69 mm⁻¹
b = 4.5667 (1) Å	T = 150 K
c = 16.3259 (4) Å	0.20 × 0.12 × 0.09 mm
β = 106.548 (1)°

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	2282 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2014)	2084 reflections with I > 2σ(I)
T_min = 0.89, T_max = 0.94	R_int = 0.035
21843 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.136	H-atom parameters constrained
S = 1.11	Δρ_max = 0.30 e Å⁻³
2282 reflections	Δρ_min = −0.22 e Å⁻³
155 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)

are estimated using the full covariance matrix. The cell e.s.d.'s are taken

into account individually in the estimation of e.s.d.'s in distances, angles

and torsion angles; correlations between e.s.d.'s in cell parameters are only

used when they are defined by crystal symmetry. An approximate (isotropic)

treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 Å) while those attached to nitrogen were placed in locations derived from a difference map and their parameters adjusted to give N—H = 0.91 Å. All were included as riding contributions with isotropic displacement parameters 1.2 times those of the attached atoms. In the final stages of the refinement, analysis of the data with the TWINROTMAT routine in PLATON (Spek, 2014) indicated the presence of a minor twin component rotated by approximately 180° about b and the data were finally refined as a 2-component twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.44188 (9)	0.4790 (3)	0.32769 (9)	0.0300 (3)
N1	0.48770 (11)	0.0380 (4)	0.29093 (11)	0.0309 (4)
H1A	0.4911	−0.1584	0.3007	0.037*
N2	0.40020 (11)	0.0618 (3)	0.38000 (10)	0.0277 (4)
H2A	0.3974	−0.1368	0.3754	0.033*
N3	0.22413 (12)	0.1572 (4)	0.29992 (12)	0.0413 (5)
H3A	0.2521	0.0112	0.2807	0.050*
H3B	0.1655	0.1521	0.2808	0.050*
C1	0.53488 (14)	0.1492 (4)	0.23655 (13)	0.0305 (4)
C2	0.49906 (16)	0.3542 (5)	0.17311 (13)	0.0383 (5)
H2	0.4428	0.4293	0.1667	0.046*
C3	0.5467 (2)	0.4474 (6)	0.11924 (16)	0.0510 (7)
H3	0.5235	0.5916	0.0770	0.061*
C4	0.6271 (2)	0.3331 (6)	0.12642 (18)	0.0551 (7)
H4	0.6587	0.3957	0.0886	0.066*
C5	0.66188 (18)	0.1280 (6)	0.18846 (17)	0.0499 (6)
H5	0.7171	0.0472	0.1929	0.060*
C6	0.61656 (15)	0.0386 (5)	0.24462 (15)	0.0396 (5)
H6	0.6415	−0.0982	0.2885	0.048*
C7	0.44317 (12)	0.2076 (4)	0.33236 (11)	0.0255 (4)
C8	0.34822 (13)	0.2198 (4)	0.42286 (12)	0.0269 (4)
C9	0.38565 (15)	0.3407 (5)	0.50231 (13)	0.0371 (5)
H9	0.4453	0.3114	0.5294	0.045*
C10	0.33681 (18)	0.5047 (6)	0.54293 (15)	0.0464 (6)
H10	0.3628	0.5887	0.5974	0.056*
C11	0.25015 (18)	0.5444 (5)	0.50347 (16)	0.0464 (6)
H11	0.2164	0.6563	0.5310	0.056*
C12	0.21204 (15)	0.4233 (5)	0.42441 (15)	0.0412 (5)
H12	0.1521	0.4522	0.3982	0.049*
C13	0.26029 (13)	0.2584 (5)	0.38210 (13)	0.0317 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0377 (8)	0.0201 (7)	0.0356 (7)	−0.0009 (6)	0.0158 (6)	0.0009 (5)
N1	0.0379 (9)	0.0210 (8)	0.0393 (9)	0.0002 (7)	0.0199 (8)	0.0012 (7)
N2	0.0328 (9)	0.0195 (7)	0.0337 (8)	−0.0002 (6)	0.0139 (7)	0.0009 (7)
N3	0.0359 (10)	0.0442 (11)	0.0404 (10)	0.0007 (8)	0.0052 (8)	−0.0010 (9)
C1	0.0385 (11)	0.0244 (9)	0.0318 (10)	−0.0071 (8)	0.0154 (9)	−0.0064 (8)
C2	0.0501 (13)	0.0326 (11)	0.0342 (11)	0.0000 (10)	0.0153 (10)	−0.0020 (9)
C3	0.083 (2)	0.0362 (12)	0.0401 (12)	−0.0022 (13)	0.0283 (13)	0.0036 (10)
C4	0.0785 (19)	0.0447 (14)	0.0600 (16)	−0.0137 (13)	0.0486 (15)	−0.0063 (12)
C5	0.0494 (14)	0.0487 (14)	0.0619 (16)	−0.0061 (12)	0.0327 (13)	−0.0065 (12)
C6	0.0407 (12)	0.0385 (12)	0.0431 (12)	−0.0007 (10)	0.0174 (10)	−0.0010 (10)
C7	0.0259 (9)	0.0230 (9)	0.0269 (9)	−0.0003 (7)	0.0065 (7)	0.0004 (7)
C8	0.0330 (10)	0.0206 (9)	0.0297 (9)	0.0011 (8)	0.0131 (8)	0.0035 (7)
C9	0.0405 (12)	0.0368 (11)	0.0336 (11)	−0.0022 (9)	0.0099 (9)	−0.0012 (9)
C10	0.0632 (16)	0.0434 (13)	0.0363 (11)	−0.0043 (12)	0.0199 (11)	−0.0097 (10)
C11	0.0632 (16)	0.0364 (12)	0.0520 (14)	0.0065 (11)	0.0361 (13)	−0.0019 (11)
C12	0.0373 (12)	0.0406 (13)	0.0505 (13)	0.0083 (10)	0.0201 (10)	0.0076 (10)
C13	0.0346 (11)	0.0300 (10)	0.0322 (10)	−0.0003 (8)	0.0120 (8)	0.0053 (8)

Geometric parameters (Å, º) top

O1—C7	1.241 (2)	C4—C5	1.377 (4)
N1—C7	1.362 (2)	C4—H4	0.9500
N1—C1	1.419 (2)	C5—C6	1.388 (3)
N1—H1A	0.9099	C5—H5	0.9500
N2—C7	1.356 (2)	C6—H6	0.9500
N2—C8	1.433 (2)	C8—C9	1.381 (3)
N2—H2A	0.9099	C8—C13	1.399 (3)
N3—C13	1.381 (3)	C9—C10	1.387 (3)
N3—H3A	0.9101	C9—H9	0.9500
N3—H3B	0.9101	C10—C11	1.378 (4)
C1—C6	1.385 (3)	C10—H10	0.9500
C1—C2	1.394 (3)	C11—C12	1.378 (4)
C2—C3	1.391 (3)	C11—H11	0.9500
C2—H2	0.9500	C12—C13	1.400 (3)
C3—C4	1.375 (4)	C12—H12	0.9500
C3—H3	0.9500

C7—N1—C1	124.19 (16)	C1—C6—C5	119.9 (2)
C7—N1—H1A	119.2	C1—C6—H6	120.0
C1—N1—H1A	116.5	C5—C6—H6	120.0
C7—N2—C8	120.03 (15)	O1—C7—N2	121.53 (17)
C7—N2—H2A	117.6	O1—C7—N1	122.64 (17)
C8—N2—H2A	121.4	N2—C7—N1	115.82 (16)
C13—N3—H3A	117.7	C9—C8—C13	120.72 (18)
C13—N3—H3B	117.0	C9—C8—N2	119.93 (18)
H3A—N3—H3B	115.7	C13—C8—N2	119.31 (17)
C6—C1—C2	119.93 (19)	C8—C9—C10	120.5 (2)
C6—C1—N1	118.56 (19)	C8—C9—H9	119.7
C2—C1—N1	121.43 (19)	C10—C9—H9	119.7
C3—C2—C1	119.2 (2)	C11—C10—C9	119.3 (2)
C3—C2—H2	120.4	C11—C10—H10	120.3
C1—C2—H2	120.4	C9—C10—H10	120.3
C4—C3—C2	120.7 (2)	C12—C11—C10	120.6 (2)
C4—C3—H3	119.6	C12—C11—H11	119.7
C2—C3—H3	119.6	C10—C11—H11	119.7
C3—C4—C5	119.9 (2)	C11—C12—C13	121.0 (2)
C3—C4—H4	120.0	C11—C12—H12	119.5
C5—C4—H4	120.0	C13—C12—H12	119.5
C4—C5—C6	120.3 (2)	N3—C13—C8	120.78 (18)
C4—C5—H5	119.9	N3—C13—C12	121.2 (2)
C6—C5—H5	119.9	C8—C13—C12	117.83 (19)

C7—N1—C1—C6	135.3 (2)	C7—N2—C8—C9	−84.9 (2)
C7—N1—C1—C2	−48.0 (3)	C7—N2—C8—C13	92.9 (2)
C6—C1—C2—C3	−0.8 (3)	C13—C8—C9—C10	−0.5 (3)
N1—C1—C2—C3	−177.4 (2)	N2—C8—C9—C10	177.3 (2)
C1—C2—C3—C4	2.0 (4)	C8—C9—C10—C11	0.5 (4)
C2—C3—C4—C5	−1.2 (4)	C9—C10—C11—C12	−0.1 (4)
C3—C4—C5—C6	−0.9 (4)	C10—C11—C12—C13	−0.3 (4)
C2—C1—C6—C5	−1.2 (3)	C9—C8—C13—N3	174.9 (2)
N1—C1—C6—C5	175.5 (2)	N2—C8—C13—N3	−2.9 (3)
C4—C5—C6—C1	2.1 (4)	C9—C8—C13—C12	0.1 (3)
C8—N2—C7—O1	3.2 (3)	N2—C8—C13—C12	−177.65 (17)
C8—N2—C7—N1	−177.12 (17)	C11—C12—C13—N3	−174.5 (2)
C1—N1—C7—O1	−1.9 (3)	C11—C12—C13—C8	0.2 (3)
C1—N1—C7—N2	178.46 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1ⁱ	0.91	2.13	2.932 (2)	147
N1—H1A···O1ⁱ	0.91	1.94	2.771 (2)	151
N3—H3A···N3ⁱⁱ	0.91	2.19	3.057 (3)	160
N3—H3B···O1ⁱⁱ	0.91	2.24	3.004 (2)	141

Symmetry codes: (i) x, y−1, z; (ii) −x+1/2, y−1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1ⁱ	0.91	2.13	2.932 (2)	147
N1—H1A···O1ⁱ	0.91	1.94	2.771 (2)	151
N3—H3A···N3ⁱⁱ	0.91	2.19	3.057 (3)	160
N3—H3B···O1ⁱⁱ	0.91	2.24	3.004 (2)	141

Symmetry codes: (i) x, y−1, z; (ii) −x+1/2, y−1/2, −z+1/2.

Acknowledgements

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.

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