1-[3-(Hy-droxy-meth-yl)phen-yl]-3-phenyl-urea.

In the title compound, C(14)H(14)N(2)O(2), the dihedral angle between the benzene rings is 23.6 (1)°. The H atoms of the urea NH groups are positioned syn to each other. In the crystal, inter-molecular N-H⋯O and O-H⋯O hydrogen bonds link the mol-ecules into a three-dimensional network.

Related literature

For general background to melanin, see: Kubo et al. (2000 ▶); Claus & Decker (2006 ▶). For the development of tyrosinase inhibitors, see: Khan et al. (2006 ▶); Kojima et al. (1995 ▶); Cabanes et al. (1994 ▶); Casañola-Martin et al. (2006 ▶); Son et al. (2000 ▶); Hong et al. (2008 ▶); Lee et al. (2007 ▶); Yi et al. (2010 ▶); Choi et al. (2010 ▶).

Experimental

Crystal data

C14H14N2O2

M = 242.27

Monoclinic,

a = 14.6207 (8) Å

b = 7.0692 (4) Å

c = 12.4019 (5) Å

β = 109.818 (3)°

V = 1205.90 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.22 × 0.21 × 0.05 mm

Data collection

Bruker SMART CCD area-detector diffractometer

9960 measured reflections

2694 independent reflections

1664 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.111

S = 0.93

2694 reflections

175 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811028315/im2305sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811028315/im2305Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811028315/im2305Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C14H14N2O2	F(000) = 512
Mr = 242.27	Dx = 1.334 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2624 reflections
a = 14.6207 (8) Å	θ = 3.2–28.0°
b = 7.0692 (4) Å	µ = 0.09 mm−1
c = 12.4019 (5) Å	T = 296 K
β = 109.818 (3)°	Plate, colourless
V = 1205.90 (11) Å3	0.22 × 0.21 × 0.05 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	Rint = 0.052
φ and ω scans	θmax = 27.5°, θmin = 3.0°
9960 measured reflections	h = −15→18
2694 independent reflections	k = −9→6
1664 reflections with I > 2σ(I)	l = −16→9

Refinement on F2	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.041	w = 1/[σ2(Fo2) + (0.0584P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.111	(Δ/σ)max < 0.001
S = 0.93	Δρmax = 0.14 e Å−3
2694 reflections	Δρmin = −0.21 e Å−3
175 parameters

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.

	x	y	z	Uiso*/Ueq
C1	0.13667 (11)	0.36148 (19)	0.11590 (11)	0.0385 (3)
C2	0.07277 (11)	0.2820 (2)	0.01677 (13)	0.0471 (4)
H2	0.0933	0.2595	−0.0453	0.057*
C3	−0.02094 (12)	0.2359 (2)	0.00922 (14)	0.0546 (4)
H3	−0.0632	0.1839	−0.0581	0.066*
C4	−0.05198 (12)	0.2664 (2)	0.10023 (15)	0.0581 (5)
H4	−0.1149	0.2343	0.0955	0.07*
C5	0.01144 (13)	0.3456 (3)	0.19916 (15)	0.0619 (5)
H5	−0.0093	0.3672	0.2611	0.074*
C6	0.10517 (12)	0.3932 (2)	0.20757 (12)	0.0524 (4)
H6	0.147	0.4464	0.2748	0.063*
N7	0.22912 (9)	0.41144 (18)	0.11382 (11)	0.0442 (3)
H7	0.2359 (11)	0.410 (2)	0.0471 (14)	0.049 (4)*
C8	0.31390 (11)	0.42001 (18)	0.20514 (11)	0.0381 (3)
O9	0.31723 (8)	0.41011 (14)	0.30535 (8)	0.0495 (3)
N10	0.39322 (9)	0.44032 (17)	0.17245 (10)	0.0436 (3)
H10	0.3815 (11)	0.444 (2)	0.0964 (15)	0.057 (5)*
C11	0.49231 (11)	0.43970 (18)	0.24098 (11)	0.0369 (3)
C12	0.52658 (11)	0.44241 (19)	0.35949 (12)	0.0454 (4)
H12	0.4834	0.4428	0.3999	0.055*
C13	0.62598 (12)	0.4446 (2)	0.41732 (13)	0.0516 (4)
H13	0.6491	0.4462	0.497	0.062*
C14	0.69114 (12)	0.4444 (2)	0.35936 (13)	0.0481 (4)
H14	0.7576	0.4466	0.3997	0.058*
C15	0.65760 (11)	0.44079 (19)	0.24059 (12)	0.0426 (4)
C16	0.55875 (11)	0.43755 (19)	0.18285 (12)	0.0423 (4)
H16	0.5359	0.4338	0.1032	0.051*
C17	0.72705 (12)	0.4432 (2)	0.17456 (14)	0.0554 (4)
H17A	0.7921	0.4684	0.2272	0.066*
H17B	0.7276	0.319	0.1415	0.066*
O18	0.70325 (8)	0.58030 (19)	0.08550 (9)	0.0559 (3)
H18	0.6949 (15)	0.685 (3)	0.1155 (18)	0.094 (8)*

	U11	U22	U33	U12	U13	U23
C1	0.0402 (9)	0.0407 (8)	0.0384 (7)	0.0035 (6)	0.0184 (6)	0.0040 (6)
C2	0.0471 (10)	0.0508 (9)	0.0476 (8)	0.0011 (7)	0.0216 (7)	−0.0047 (7)
C3	0.0484 (11)	0.0514 (10)	0.0634 (10)	−0.0044 (8)	0.0181 (8)	−0.0058 (8)
C4	0.0434 (11)	0.0665 (11)	0.0697 (11)	0.0000 (8)	0.0260 (9)	0.0141 (9)
C5	0.0524 (12)	0.0909 (13)	0.0525 (10)	0.0108 (10)	0.0309 (9)	0.0147 (9)
C6	0.0459 (11)	0.0747 (11)	0.0400 (8)	0.0060 (8)	0.0190 (7)	0.0029 (8)
N7	0.0395 (8)	0.0641 (9)	0.0327 (6)	−0.0023 (6)	0.0169 (6)	0.0007 (6)
C8	0.0433 (9)	0.0383 (8)	0.0361 (7)	−0.0014 (6)	0.0176 (6)	−0.0006 (6)
O9	0.0509 (7)	0.0673 (7)	0.0339 (5)	−0.0055 (5)	0.0193 (5)	−0.0011 (5)
N10	0.0411 (8)	0.0609 (8)	0.0315 (6)	−0.0035 (6)	0.0159 (5)	0.0003 (6)
C11	0.0389 (9)	0.0362 (8)	0.0353 (7)	−0.0021 (6)	0.0121 (6)	−0.0006 (6)
C12	0.0494 (11)	0.0538 (9)	0.0361 (7)	−0.0015 (7)	0.0185 (7)	−0.0032 (7)
C13	0.0521 (11)	0.0638 (11)	0.0354 (7)	0.0000 (8)	0.0103 (7)	−0.0011 (7)
C14	0.0424 (10)	0.0532 (10)	0.0452 (8)	0.0018 (7)	0.0103 (7)	−0.0009 (7)
C15	0.0436 (10)	0.0410 (8)	0.0455 (8)	0.0011 (7)	0.0181 (7)	−0.0005 (6)
C16	0.0421 (10)	0.0507 (9)	0.0354 (7)	−0.0029 (7)	0.0148 (6)	−0.0011 (6)
C17	0.0457 (11)	0.0697 (11)	0.0539 (9)	0.0013 (8)	0.0210 (8)	−0.0028 (8)
O18	0.0630 (8)	0.0707 (9)	0.0428 (6)	−0.0048 (6)	0.0294 (6)	−0.0059 (6)

C1—C6	1.3820 (19)	N10—H10	0.900 (17)
C1—C2	1.386 (2)	C11—C12	1.3829 (19)
C1—N7	1.4058 (19)	C11—C16	1.392 (2)
C2—C3	1.380 (2)	C12—C13	1.386 (2)
C2—H2	0.93	C12—H12	0.93
C3—C4	1.369 (2)	C13—C14	1.374 (2)
C3—H3	0.93	C13—H13	0.93
C4—C5	1.381 (2)	C14—C15	1.386 (2)
C4—H4	0.93	C14—H14	0.93
C5—C6	1.380 (2)	C15—C16	1.379 (2)
C5—H5	0.93	C15—C17	1.505 (2)
C6—H6	0.93	C16—H16	0.93
N7—C8	1.3678 (19)	C17—O18	1.421 (2)
N7—H7	0.866 (17)	C17—H17A	0.97
C8—O9	1.2291 (15)	C17—H17B	0.97
C8—N10	1.3597 (18)	O18—H18	0.86 (2)
N10—C11	1.4094 (18)
C6—C1—C2	118.88 (14)	C11—N10—H10	115.1 (10)
C6—C1—N7	124.41 (14)	C12—C11—C16	119.05 (14)
C2—C1—N7	116.66 (12)	C12—C11—N10	124.67 (13)
C3—C2—C1	120.73 (14)	C16—C11—N10	116.28 (12)
C3—C2—H2	119.6	C11—C12—C13	119.26 (14)
C1—C2—H2	119.6	C11—C12—H12	120.4
C4—C3—C2	120.39 (16)	C13—C12—H12	120.4
C4—C3—H3	119.8	C14—C13—C12	121.38 (14)
C2—C3—H3	119.8	C14—C13—H13	119.3
C3—C4—C5	119.08 (15)	C12—C13—H13	119.3
C3—C4—H4	120.5	C13—C14—C15	119.84 (15)
C5—C4—H4	120.5	C13—C14—H14	120.1
C6—C5—C4	121.08 (15)	C15—C14—H14	120.1
C6—C5—H5	119.5	C16—C15—C14	118.90 (14)
C4—C5—H5	119.5	C16—C15—C17	119.96 (13)
C5—C6—C1	119.84 (15)	C14—C15—C17	121.13 (14)
C5—C6—H6	120.1	C15—C16—C11	121.56 (13)
C1—C6—H6	120.1	C15—C16—H16	119.2
C8—N7—C1	127.08 (12)	C11—C16—H16	119.2
C8—N7—H7	115.2 (10)	O18—C17—C15	113.44 (13)
C1—N7—H7	116.0 (10)	O18—C17—H17A	108.9
O9—C8—N10	124.20 (14)	C15—C17—H17A	108.9
O9—C8—N7	123.29 (13)	O18—C17—H17B	108.9
N10—C8—N7	112.51 (12)	C15—C17—H17B	108.9
C8—N10—C11	128.77 (12)	H17A—C17—H17B	107.7
C8—N10—H10	115.9 (10)	C17—O18—H18	106.6 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N7—H7···O18i	0.87 (2)	2.12 (2)	2.958 (2)	163 (1)
N10—H10···O18i	0.90 (2)	2.18 (2)	3.031 (2)	157 (1)
O18—H18···O9ii	0.86 (2)	1.91 (2)	2.763 (2)	175 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N7—H7⋯O18i	0.87 (2)	2.12 (2)	2.958 (2)	163 (1)
N10—H10⋯O18i	0.90 (2)	2.18 (2)	3.031 (2)	157 (1)
O18—H18⋯O9ii	0.86 (2)	1.91 (2)	2.763 (2)	175 (2)

Symmetry codes: (i) ; (ii) .