Crystal structure of 1-(2-amino-phen-yl)-3-phenyl-urea.

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 amino-phenyl ring is 84.43 (7)°. In the crystal, mol-ecules 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 mol-ecules, forming columns propagating along [010]. The structure was refined as a two-component twin with a 0.933 (3):0.067 (3) domain ratio.

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 ▸).

Experimental

Crystal data

C13H13N3O

M = 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

Δρmax = 0.30 e Å−3

Δρmin = −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 ▸).

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

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

Click here for additional data file.

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

Click here for additional data file.

. 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.

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

C13H13N3O	F(000) = 480
Mr = 227.26	Dx = 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

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	Rint = 0.035
Detector resolution: 10.4167 pixels mm-1	θmax = 72.5°, θmin = 2.8°
ω scans	h = −19→17
Absorption correction: multi-scan (SADABS; Bruker, 2014)	k = −5→5
Tmin = 0.89, Tmax = 0.94	l = −20→20
21843 measured reflections

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(Fo2) + (0.054P)2 + 0.8485P] where P = (Fo2 + 2Fc2)/3
2282 reflections	(Δ/σ)max < 0.001
155 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused 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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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

Symmetry codes: (i) ; (ii) .