N-(2,5-Dimeth-oxy-phen-yl)-N'-(4-hy-droxy-pheneth-yl)urea.

In the title compound, C(17)H(20)N(2)O(4), the 2,5-dimeth-oxy-phenyl unit is almost planar, with an r.m.s. deviation of 0.015 Å. The dihedral angle between the 2,5-dimeth-oxy-phenyl ring and the urea plane is 20.95 (8)°. The H atoms of the urea NH groups are positioned syn to each other. The mol-ecular structure is stabilized by a short intra-molecular N-H⋯O hydrogen bond. 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 tyrosinase, see: Kubo et al. (2000 ▶); Perez-Gilbert & Garcia-Carmona (2001 ▶). For the development of tyrosinase inhibitors, see: Shiino et al. (2001 ▶); Khan et al. (2006 ▶); Garcia & Fulrton (1996 ▶); Kojima et al. (1995 ▶); Cabanes et al. (1994 ▶); Lemic-Stojcevic et al. 1995 ▶); Casanola-Martin et al. (2006 ▶); Thanigaimalai et al. (2010 ▶); Passi & Nazzaro-Porro (1981 ▶).

Experimental

Crystal data

C17H20N2O4

M = 316.35

Monoclinic,

a = 10.7275 (6) Å

b = 9.6016 (5) Å

c = 16.9388 (10) Å

β = 107.838 (2)°

V = 1660.84 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.31 × 0.27 × 0.13 mm

Data collection

Bruker SMART CCD area-detector diffractometer

13358 measured reflections

3184 independent reflections

2296 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.186

S = 1.06

3184 reflections

218 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.46 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: DIAMOND (Brandenburg, 2010 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810038535/jh2214sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810038535/jh2214Isup2.hkl

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

C17H20N2O4	F(000) = 672
Mr = 316.35	Dx = 1.265 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5519 reflections
a = 10.7275 (6) Å	θ = 2.5–27.8°
b = 9.6016 (5) Å	µ = 0.09 mm−1
c = 16.9388 (10) Å	T = 296 K
β = 107.838 (2)°	Needle, colourless
V = 1660.84 (16) Å3	0.31 × 0.27 × 0.13 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	Rint = 0.044
φ and ω scans	θmax = 26.0°, θmin = 2.0°
13358 measured reflections	h = −13→6
3184 independent reflections	k = −11→9
2296 reflections with I > 2σ(I)	l = −20→16

Refinement on F2	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.059	w = 1/[σ2(Fo2) + (0.0966P)2 + 0.4089P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.186	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.32 e Å−3
3184 reflections	Δρmin = −0.46 e Å−3
218 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	0.3898 (2)	0.5854 (2)	0.12845 (14)	0.0581 (5)
C2	0.5212 (2)	0.6136 (3)	0.13837 (16)	0.0698 (7)
C3	0.5565 (3)	0.6644 (3)	0.0720 (2)	0.0856 (8)
H3	0.644	0.6835	0.0783	0.103*
C4	0.4643 (3)	0.6869 (3)	−0.00277 (19)	0.0845 (8)
H4	0.4896	0.7201	−0.0471	0.101*
C5	0.3347 (3)	0.6610 (3)	−0.01298 (15)	0.0724 (7)
C6	0.2967 (2)	0.6085 (2)	0.05238 (14)	0.0636 (6)
H6	0.209	0.589	0.0452	0.076*
N7	0.35963 (18)	0.5297 (2)	0.19699 (12)	0.0639 (5)
H7	0.423 (3)	0.498 (3)	0.2325 (16)	0.068 (7)*
C8	0.24229 (19)	0.5317 (2)	0.21258 (12)	0.0540 (5)
O9	0.14248 (14)	0.58188 (19)	0.16417 (9)	0.0701 (5)
N10	0.24242 (19)	0.4718 (2)	0.28412 (11)	0.0638 (5)
H10	0.315 (3)	0.441 (3)	0.3168 (16)	0.075 (8)*
C11	0.1271 (2)	0.4629 (3)	0.31035 (13)	0.0683 (7)
H11A	0.1342	0.3814	0.3453	0.082*
H11B	0.0514	0.4501	0.2618	0.082*
C12	0.1046 (2)	0.5896 (3)	0.35756 (13)	0.0684 (7)
H12A	0.0949	0.6706	0.322	0.082*
H12B	0.0231	0.5774	0.3703	0.082*
C13	0.21277 (19)	0.6172 (2)	0.43716 (13)	0.0558 (5)
C14	0.2326 (3)	0.5296 (3)	0.50382 (15)	0.0820 (8)
H14	0.1792	0.4519	0.4992	0.098*
C15	0.3299 (3)	0.5540 (3)	0.57772 (16)	0.0874 (9)
H15	0.3413	0.4926	0.6219	0.105*
C16	0.40944 (19)	0.6679 (2)	0.58626 (13)	0.0597 (6)
C17	0.3892 (2)	0.7585 (2)	0.52187 (14)	0.0638 (6)
H17	0.4404	0.8383	0.5274	0.077*
C18	0.2917 (2)	0.7315 (2)	0.44770 (14)	0.0654 (6)
H18	0.2798	0.7935	0.4038	0.078*
O19	0.50449 (17)	0.6876 (2)	0.66089 (11)	0.0816 (6)
H19	0.552 (3)	0.759 (4)	0.658 (2)	0.122*
O20	0.60539 (16)	0.5880 (3)	0.21599 (12)	0.0954 (7)
C21	0.7414 (3)	0.6140 (7)	0.2294 (2)	0.1518 (19)
H21A	0.7898	0.5914	0.2857	0.228*
H21B	0.7541	0.7105	0.2192	0.228*
H21C	0.7719	0.5574	0.1923	0.228*
O22	0.2495 (2)	0.6902 (3)	−0.08960 (12)	0.0991 (7)
C23	0.1155 (4)	0.6852 (3)	−0.10046 (19)	0.1056 (11)
H23A	0.0681	0.7078	−0.1569	0.158*
H23B	0.094	0.7512	−0.064	0.158*
H23C	0.0919	0.5933	−0.0879	0.158*

	U11	U22	U33	U12	U13	U23
C1	0.0566 (11)	0.0614 (13)	0.0551 (12)	0.0002 (9)	0.0154 (10)	−0.0068 (10)
C2	0.0567 (13)	0.0777 (16)	0.0735 (15)	−0.0004 (11)	0.0175 (12)	−0.0106 (12)
C3	0.0665 (15)	0.097 (2)	0.100 (2)	−0.0084 (14)	0.0355 (15)	−0.0010 (17)
C4	0.0879 (18)	0.0901 (19)	0.0855 (19)	−0.0109 (15)	0.0411 (16)	0.0065 (15)
C5	0.0828 (16)	0.0724 (16)	0.0603 (14)	−0.0089 (12)	0.0195 (12)	0.0028 (11)
C6	0.0610 (12)	0.0702 (15)	0.0565 (13)	−0.0088 (10)	0.0135 (10)	−0.0019 (11)
N7	0.0488 (10)	0.0852 (14)	0.0512 (11)	0.0095 (9)	0.0059 (8)	0.0050 (9)
C8	0.0531 (11)	0.0588 (12)	0.0426 (10)	0.0045 (9)	0.0037 (9)	−0.0033 (9)
O9	0.0538 (8)	0.0941 (12)	0.0551 (9)	0.0151 (8)	0.0057 (7)	0.0144 (8)
N10	0.0603 (11)	0.0815 (13)	0.0453 (10)	0.0137 (9)	0.0100 (8)	0.0071 (9)
C11	0.0644 (13)	0.0858 (17)	0.0483 (12)	−0.0152 (11)	0.0079 (10)	−0.0045 (11)
C12	0.0465 (11)	0.1008 (18)	0.0511 (12)	0.0057 (11)	0.0050 (9)	−0.0050 (12)
C13	0.0456 (10)	0.0698 (14)	0.0466 (11)	0.0055 (9)	0.0061 (8)	−0.0026 (10)
C14	0.0843 (17)	0.0838 (17)	0.0614 (14)	−0.0297 (14)	−0.0020 (12)	0.0050 (13)
C15	0.1003 (19)	0.0795 (17)	0.0587 (14)	−0.0219 (15)	−0.0109 (13)	0.0176 (13)
C16	0.0501 (11)	0.0611 (13)	0.0541 (12)	0.0033 (9)	−0.0044 (9)	0.0008 (10)
C17	0.0597 (12)	0.0574 (12)	0.0646 (13)	−0.0045 (10)	0.0047 (10)	0.0023 (10)
C18	0.0679 (14)	0.0651 (14)	0.0544 (12)	0.0060 (11)	0.0056 (10)	0.0120 (10)
O19	0.0738 (11)	0.0760 (12)	0.0659 (10)	−0.0059 (8)	−0.0214 (8)	0.0041 (8)
O20	0.0496 (9)	0.1491 (19)	0.0801 (12)	0.0044 (10)	0.0088 (8)	−0.0044 (12)
C21	0.0506 (16)	0.283 (6)	0.114 (3)	−0.004 (2)	0.0139 (17)	−0.020 (3)
O22	0.0948 (14)	0.1328 (18)	0.0650 (11)	−0.0083 (12)	0.0173 (10)	0.0177 (11)
C23	0.136 (3)	0.073	0.0813 (19)	−0.0271 (17)	−0.0063 (19)	0.0146 (15)

C1—C6	1.385 (3)	C12—H12A	0.97
C1—C2	1.394 (3)	C12—H12B	0.97
C1—N7	1.403 (3)	C13—C18	1.364 (3)
C2—O20	1.370 (3)	C13—C14	1.371 (3)
C2—C3	1.381 (4)	C14—C15	1.382 (3)
C3—C4	1.364 (4)	C14—H14	0.93
C3—H3	0.93	C15—C16	1.367 (3)
C4—C5	1.370 (4)	C15—H15	0.93
C4—H4	0.93	C16—C17	1.360 (3)
C5—O22	1.368 (3)	C16—O19	1.373 (2)
C5—C6	1.387 (3)	C17—C18	1.391 (3)
C6—H6	0.93	C17—H17	0.93
N7—C8	1.363 (3)	C18—H18	0.93
N7—H7	0.82 (3)	O19—H19	0.86 (4)
C8—O9	1.230 (2)	O20—C21	1.429 (3)
C8—N10	1.341 (3)	C21—H21A	0.96
N10—C11	1.440 (3)	C21—H21B	0.96
N10—H10	0.86 (3)	C21—H21C	0.96
C11—C12	1.515 (4)	O22—C23	1.394 (4)
C11—H11A	0.97	C23—H23A	0.96
C11—H11B	0.97	C23—H23B	0.96
C12—C13	1.509 (3)	C23—H23C	0.96
C6—C1—C2	119.7 (2)	C13—C12—H12B	108.7
C6—C1—N7	123.2 (2)	C11—C12—H12B	108.7
C2—C1—N7	117.1 (2)	H12A—C12—H12B	107.6
O20—C2—C3	125.5 (2)	C18—C13—C14	116.88 (19)
O20—C2—C1	115.2 (2)	C18—C13—C12	122.3 (2)
C3—C2—C1	119.3 (2)	C14—C13—C12	120.8 (2)
C4—C3—C2	120.7 (2)	C13—C14—C15	121.7 (2)
C4—C3—H3	119.7	C13—C14—H14	119.1
C2—C3—H3	119.7	C15—C14—H14	119.1
C3—C4—C5	120.5 (3)	C16—C15—C14	120.3 (2)
C3—C4—H4	119.7	C16—C15—H15	119.8
C5—C4—H4	119.7	C14—C15—H15	119.8
O22—C5—C4	116.1 (2)	C17—C16—C15	119.08 (19)
O22—C5—C6	123.9 (2)	C17—C16—O19	122.8 (2)
C4—C5—C6	120.0 (2)	C15—C16—O19	118.1 (2)
C1—C6—C5	119.8 (2)	C16—C17—C18	119.7 (2)
C1—C6—H6	120.1	C16—C17—H17	120.1
C5—C6—H6	120.1	C18—C17—H17	120.1
C8—N7—C1	127.99 (19)	C13—C18—C17	122.2 (2)
C8—N7—H7	118.4 (18)	C13—C18—H18	118.9
C1—N7—H7	113.4 (18)	C17—C18—H18	118.9
O9—C8—N10	122.0 (2)	C16—O19—H19	110 (2)
O9—C8—N7	122.9 (2)	C2—O20—C21	117.5 (3)
N10—C8—N7	115.05 (18)	O20—C21—H21A	109.5
C8—N10—C11	122.76 (19)	O20—C21—H21B	109.5
C8—N10—H10	118.8 (17)	H21A—C21—H21B	109.5
C11—N10—H10	118.4 (17)	O20—C21—H21C	109.5
N10—C11—C12	114.0 (2)	H21A—C21—H21C	109.5
N10—C11—H11A	108.8	H21B—C21—H21C	109.5
C12—C11—H11A	108.8	C5—O22—C23	118.7 (2)
N10—C11—H11B	108.8	O22—C23—H23A	109.5
C12—C11—H11B	108.8	O22—C23—H23B	109.5
H11A—C11—H11B	107.7	H23A—C23—H23B	109.5
C13—C12—C11	114.19 (19)	O22—C23—H23C	109.5
C13—C12—H12A	108.7	H23A—C23—H23C	109.5
C11—C12—H12A	108.7	H23B—C23—H23C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N7—H7···O20	0.82 (3)	2.23 (2)	2.617 (3)	109 (2)
N7—H7···O19i	0.82 (3)	2.48 (3)	3.182 (3)	144 (2)
N10—H10···O19i	0.86 (3)	2.23 (3)	3.005 (3)	150 (2)
O19—H19···O9ii	0.86 (4)	1.80 (4)	2.654 (3)	172 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N7—H7⋯O20	0.82 (3)	2.23 (2)	2.617 (3)	109 (2)
N7—H7⋯O19i	0.82 (3)	2.48 (3)	3.182 (3)	144 (2)
N10—H10⋯O19i	0.86 (3)	2.23 (3)	3.005 (3)	150 (2)
O19—H19⋯O9ii	0.86 (4)	1.80 (4)	2.654 (3)	172 (4)

Symmetry codes: (i) ; (ii) .