1-(2-Hy-droxy-2-phenyl-eth-yl)-3-(4-meth-oxy-phen-yl)urea.

In the title compound, C(16)H(18)N(2)O(3), the dihedral angle between the 4-meth-oxy-phenyl ring and the urea group is 35.6 (2) °. 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 two-dimensional array in the ac plane; the carbonyl-O atom is trifurcated.

Related literature

For general background to melanin, see: Prota (1988 ▶). For the development of potent inhibitory agents of tyrosinase, see: Khan et al. (2006 ▶); Kojima et al. (1995 ▶); Cabanes et al. (1994 ▶); Son et al. (2000 ▶); Iida et al. (1995 ▶).

Experimental

Crystal data

C16H18N2O3

M = 286.32

Monoclinic,

a = 6.8120 (6) Å

b = 8.7659 (7) Å

c = 12.1393 (10) Å

β = 97.009 (3)°

V = 719.46 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.07 × 0.05 × 0.03 mm

Data collection

Bruker SMART CCD area-detector diffractometer

5017 measured reflections

1947 independent reflections

1782 reflections with I > 2σ(I)

R int = 0.073

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.166

S = 1.05

1947 reflections

201 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.71 e Å−3

Δρmin = −0.26 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 publication routines (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811036464/tk2785sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811036464/tk2785Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811036464/tk2785Isup3.cml

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

C16H18N2O3	F(000) = 304
Mr = 286.32	Dx = 1.322 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 4535 reflections
a = 6.8120 (6) Å	θ = 2.9–28.1°
b = 8.7659 (7) Å	µ = 0.09 mm−1
c = 12.1393 (10) Å	T = 296 K
β = 97.009 (3)°	Block, colourless
V = 719.46 (10) Å3	0.07 × 0.05 × 0.03 mm
Z = 2

Bruker SMART CCD area-detector diffractometer	Rint = 0.073
graphite	θmax = 25.5°, θmin = 1.7°
φ and ω scans	h = −7→8
5017 measured reflections	k = −5→10
1947 independent reflections	l = −7→14
1782 reflections with I > 2σ(I)

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.166	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0819P)2 + 0.6912P] where P = (Fo2 + 2Fc2)/3
1947 reflections	(Δ/σ)max < 0.001
201 parameters	Δρmax = 0.71 e Å−3
1 restraint	Δρmin = −0.26 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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.

	x	y	z	Uiso*/Ueq
C1	0.3090 (6)	0.9178 (6)	−0.2016 (4)	0.0461 (12)
C2	0.2104 (7)	0.7832 (7)	−0.1959 (4)	0.0533 (14)
H2	0.2401	0.7201	−0.1345	0.064*
C3	0.0666 (8)	0.7396 (7)	−0.2805 (4)	0.0542 (13)
H3	0.0017	0.6469	−0.2758	0.065*
C4	0.0191 (7)	0.8310 (7)	−0.3707 (4)	0.0505 (13)
H4	−0.0787	0.8012	−0.4268	0.061*
C5	0.1151 (7)	0.9660 (7)	−0.3783 (4)	0.0530 (14)
H5	0.0838	1.0293	−0.4394	0.064*
C6	0.2616 (7)	1.0081 (7)	−0.2929 (5)	0.0571 (14)
H6	0.3285	1.0998	−0.2983	0.069*
C7	0.4712 (7)	0.9574 (7)	−0.1086 (5)	0.0613 (16)
H7	0.4519	0.8924	−0.0451	0.074*
O8	0.4713 (6)	1.1060 (5)	−0.0726 (3)	0.0631 (11)
H8	0.347 (10)	1.118 (8)	−0.071 (5)	0.076*
C9	0.6694 (6)	0.9180 (6)	−0.1428 (3)	0.0378 (10)
H9A	0.6796	0.8079	−0.1485	0.045*
H9B	0.6782	0.9604	−0.2159	0.045*
N10	0.8347 (5)	0.9736 (5)	−0.0668 (3)	0.0369 (9)
H10	0.876 (8)	1.060 (7)	−0.072 (4)	0.052 (17)*
C11	0.9310 (5)	0.8900 (5)	0.0159 (3)	0.0309 (9)
O12	0.8885 (4)	0.7545 (3)	0.0342 (2)	0.0365 (7)
N13	1.0818 (5)	0.9640 (5)	0.0765 (3)	0.0345 (8)
H13	1.108 (7)	1.048 (7)	0.060 (4)	0.036 (14)*
C14	1.2036 (6)	0.9091 (5)	0.1709 (3)	0.0305 (9)
C15	1.3978 (6)	0.9599 (5)	0.1905 (3)	0.0351 (10)
H15	1.4482	1.0223	0.1387	0.042*
C16	1.5166 (6)	0.9188 (5)	0.2859 (3)	0.0349 (10)
H16	1.6459	0.9546	0.2983	0.042*
C17	1.4460 (6)	0.8252 (5)	0.3630 (3)	0.0345 (10)
C18	1.2540 (6)	0.7706 (6)	0.3442 (3)	0.0383 (10)
H18	1.2069	0.705	0.3951	0.046*
C19	1.1310 (6)	0.8140 (5)	0.2487 (3)	0.0369 (10)
H19	1.001	0.7795	0.237	0.044*
O20	1.5764 (4)	0.7926 (4)	0.4554 (2)	0.0435 (9)
C21	1.5099 (8)	0.6908 (7)	0.5350 (4)	0.0520 (13)
H21A	1.6131	0.6768	0.5954	0.078*
H21B	1.4764	0.5942	0.5005	0.078*
H21C	1.3954	0.7331	0.5626	0.078*

	U11	U22	U33	U12	U13	U23
C1	0.029 (2)	0.051 (3)	0.057 (3)	0.014 (2)	0.0003 (18)	−0.010 (3)
C2	0.045 (3)	0.067 (4)	0.048 (2)	0.015 (3)	0.010 (2)	0.003 (3)
C3	0.042 (3)	0.054 (3)	0.069 (3)	−0.007 (2)	0.016 (2)	0.004 (3)
C4	0.029 (2)	0.071 (4)	0.049 (2)	−0.004 (2)	−0.0010 (18)	−0.006 (3)
C5	0.041 (3)	0.062 (4)	0.056 (3)	0.013 (3)	0.008 (2)	0.014 (3)
C6	0.035 (3)	0.044 (3)	0.094 (4)	0.000 (2)	0.015 (3)	−0.002 (3)
C7	0.044 (3)	0.070 (4)	0.067 (3)	0.006 (3)	−0.002 (2)	−0.025 (3)
O8	0.0414 (18)	0.065 (3)	0.080 (2)	0.0104 (19)	−0.0049 (17)	−0.033 (2)
C9	0.029 (2)	0.040 (3)	0.042 (2)	0.0025 (19)	−0.0037 (16)	−0.006 (2)
N10	0.0314 (19)	0.034 (2)	0.0427 (19)	−0.0011 (17)	−0.0043 (14)	−0.0009 (18)
C11	0.0236 (18)	0.033 (2)	0.0371 (19)	0.0026 (17)	0.0090 (15)	−0.0025 (19)
O12	0.0340 (15)	0.0310 (18)	0.0438 (15)	−0.0032 (13)	0.0016 (11)	−0.0008 (13)
N13	0.0353 (19)	0.031 (2)	0.0355 (17)	−0.0055 (17)	−0.0031 (14)	0.0057 (17)
C14	0.030 (2)	0.030 (2)	0.0311 (18)	−0.0019 (18)	0.0014 (15)	−0.0015 (18)
C15	0.037 (2)	0.037 (3)	0.0305 (18)	−0.006 (2)	0.0044 (15)	−0.0015 (19)
C16	0.031 (2)	0.039 (3)	0.0342 (19)	−0.0056 (19)	0.0017 (15)	−0.0048 (19)
C17	0.039 (2)	0.035 (2)	0.0292 (18)	0.004 (2)	0.0013 (16)	−0.0045 (19)
C18	0.038 (2)	0.043 (3)	0.0347 (19)	−0.005 (2)	0.0052 (16)	0.007 (2)
C19	0.029 (2)	0.040 (3)	0.041 (2)	−0.0039 (19)	0.0045 (16)	0.000 (2)
O20	0.0412 (17)	0.049 (2)	0.0375 (15)	−0.0036 (15)	−0.0045 (12)	0.0146 (15)
C21	0.049 (3)	0.065 (4)	0.041 (2)	−0.003 (3)	−0.001 (2)	0.021 (2)

C1—C2	1.363 (8)	N10—H10	0.81 (6)
C1—C6	1.369 (7)	C11—O12	1.249 (5)
C1—C7	1.520 (7)	C11—N13	1.354 (5)
C2—C3	1.384 (7)	N13—C14	1.415 (5)
C2—H2	0.93	N13—H13	0.79 (5)
C3—C4	1.364 (8)	C14—C15	1.389 (5)
C3—H3	0.93	C14—C19	1.395 (6)
C4—C5	1.361 (8)	C15—C16	1.377 (6)
C4—H4	0.93	C15—H15	0.93
C5—C6	1.398 (7)	C16—C17	1.375 (6)
C5—H5	0.93	C16—H16	0.93
C6—H6	0.93	C17—O20	1.374 (4)
C7—O8	1.374 (7)	C17—C18	1.385 (6)
C7—C9	1.501 (7)	C18—C19	1.398 (6)
C7—H7	0.98	C18—H18	0.93
O8—H8	0.86 (7)	C19—H19	0.93
C9—N10	1.450 (5)	O20—C21	1.429 (6)
C9—H9A	0.97	C21—H21A	0.96
C9—H9B	0.97	C21—H21B	0.96
N10—C11	1.347 (5)	C21—H21C	0.96
C2—C1—C6	118.2 (4)	C9—N10—H10	121 (4)
C2—C1—C7	118.5 (5)	O12—C11—N10	123.2 (4)
C6—C1—C7	123.2 (5)	O12—C11—N13	122.4 (4)
C1—C2—C3	120.7 (5)	N10—C11—N13	114.4 (4)
C1—C2—H2	119.7	C11—N13—C14	127.5 (4)
C3—C2—H2	119.7	C11—N13—H13	119 (3)
C4—C3—C2	120.7 (5)	C14—N13—H13	113 (3)
C4—C3—H3	119.6	C15—C14—C19	119.0 (3)
C2—C3—H3	119.6	C15—C14—N13	118.8 (4)
C5—C4—C3	119.8 (5)	C19—C14—N13	122.0 (3)
C5—C4—H4	120.1	C16—C15—C14	120.7 (4)
C3—C4—H4	120.1	C16—C15—H15	119.7
C4—C5—C6	119.0 (5)	C14—C15—H15	119.7
C4—C5—H5	120.5	C17—C16—C15	120.7 (4)
C6—C5—H5	120.5	C17—C16—H16	119.7
C1—C6—C5	121.6 (5)	C15—C16—H16	119.7
C1—C6—H6	119.2	O20—C17—C16	115.8 (4)
C5—C6—H6	119.2	O20—C17—C18	124.5 (4)
O8—C7—C9	109.9 (5)	C16—C17—C18	119.7 (3)
O8—C7—C1	115.1 (4)	C17—C18—C19	120.1 (4)
C9—C7—C1	109.8 (4)	C17—C18—H18	120
O8—C7—H7	107.2	C19—C18—H18	120
C9—C7—H7	107.2	C14—C19—C18	119.8 (4)
C1—C7—H7	107.2	C14—C19—H19	120.1
C7—O8—H8	100 (5)	C18—C19—H19	120.1
N10—C9—C7	113.6 (4)	C17—O20—C21	117.1 (3)
N10—C9—H9A	108.8	O20—C21—H21A	109.5
C7—C9—H9A	108.8	O20—C21—H21B	109.5
N10—C9—H9B	108.8	H21A—C21—H21B	109.5
C7—C9—H9B	108.8	O20—C21—H21C	109.5
H9A—C9—H9B	107.7	H21A—C21—H21C	109.5
C11—N10—C9	124.1 (4)	H21B—C21—H21C	109.5
C11—N10—H10	115 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O8—H8···O12i	0.86 (7)	2.09 (7)	2.863 (5)	150 (6)
N10—H10···O12ii	0.81 (6)	2.35 (6)	3.098 (5)	153 (5)
N13—H13···O12ii	0.79 (5)	2.14 (5)	2.898 (5)	161 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O8—H8⋯O12i	0.86 (7)	2.09 (7)	2.863 (5)	150 (6)
N10—H10⋯O12ii	0.81 (6)	2.35 (6)	3.098 (5)	153 (5)
N13—H13⋯O12ii	0.79 (5)	2.14 (5)	2.898 (5)	161 (4)

Symmetry codes: (i) ; (ii) .