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

In the title compound, C(17)H(20)N(2)O(4), the 2,5-dimeth-oxy-phenyl unit is essentially planar, with an r.m.s. deviation of 0.015 Å. The dihedral angle between the benzene rings is 43.66 (4)°. 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 melanin synthesis, melanogenesis and tyrosinase, see: Francisco et al. (2006 ▶); Hearing & Jimenez (1987 ▶); Prota (1988 ▶); Grimes et al. (2006 ▶); Maeda & Fukuda (1991 ▶). For the development of potent inhibitory agents of tyrosinase and melanin formation as whitening agents, see: Ohguchi et al. (2003 ▶); Lemic-Stojcevic et al. (1995 ▶); Battaini et al. (2000 ▶); Cabanes et al. (1994 ▶); Liangli (2003 ▶); Thanigaimalai et al. (2010 ▶); Hong et al. (2008 ▶); Lee et al. (2007 ▶); Yi et al. (2009 ▶, 2010 ▶); Kwak et al. (2010 ▶); Choi et al. (2010 ▶); Germanas et al. (2007 ▶); Briganti et al. (2003 ▶).

Experimental

Crystal data

C17H20N2O4

M = 316.35

Monoclinic,

a = 18.7551 (18) Å

b = 6.8095 (6) Å

c = 12.6881 (12) Å

β = 98.930 (3)°

V = 1600.8 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.31 × 0.28 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer

13398 measured reflections

3563 independent reflections

2473 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.108

S = 1.03

3563 reflections

222 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.16 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/S1600536810033520/vm2041sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810033520/vm2041Isup2.hkl

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

C17H20N2O4	F(000) = 672
Mr = 316.35	Dx = 1.313 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4670 reflections
a = 18.7551 (18) Å	θ = 2.9–28.0°
b = 6.8095 (6) Å	µ = 0.09 mm−1
c = 12.6881 (12) Å	T = 296 K
β = 98.930 (3)°	Plate, colourless
V = 1600.8 (3) Å3	0.31 × 0.28 × 0.08 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	Rint = 0.045
φ and ω scans	θmax = 27.5°, θmin = 2.2°
13398 measured reflections	h = −20→24
3563 independent reflections	k = −8→5
2473 reflections with I > 2σ(I)	l = −16→7

Refinement on F2	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.038	w = 1/[σ2(Fo2) + (0.0527P)2 + 0.087P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.108	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.15 e Å−3
3563 reflections	Δρmin = −0.16 e Å−3
222 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	0.81571 (7)	0.4546 (2)	0.70224 (10)	0.0478 (3)
C2	0.85245 (8)	0.6263 (2)	0.68225 (10)	0.0512 (3)
C3	0.91672 (8)	0.6722 (2)	0.74533 (12)	0.0594 (4)
H3	0.9415	0.7852	0.7315	0.071*
C4	0.94471 (8)	0.5516 (2)	0.82909 (12)	0.0603 (4)
H4	0.9877	0.5848	0.8723	0.072*
C5	0.90884 (8)	0.3820 (2)	0.84865 (11)	0.0533 (3)
C6	0.84471 (8)	0.3320 (2)	0.78530 (11)	0.0515 (3)
H6	0.8211	0.2166	0.7983	0.062*
N7	0.75121 (7)	0.41428 (19)	0.63308 (9)	0.0557 (3)
H7	0.7438 (8)	0.482 (2)	0.5747 (12)	0.061 (4)*
C8	0.69226 (7)	0.31819 (18)	0.65892 (10)	0.0456 (3)
O9	0.69222 (6)	0.23814 (17)	0.74516 (8)	0.0696 (3)
N10	0.63478 (6)	0.32245 (17)	0.58002 (9)	0.0483 (3)
H10	0.6403 (7)	0.3846 (19)	0.5222 (11)	0.049 (4)*
C11	0.56284 (7)	0.26392 (17)	0.58430 (10)	0.0420 (3)
C12	0.51483 (8)	0.26886 (18)	0.48941 (10)	0.0461 (3)
H12	0.5314	0.3014	0.4263	0.055*
C13	0.44293 (8)	0.22611 (18)	0.48762 (11)	0.0475 (3)
H13	0.4118	0.2295	0.423	0.057*
C14	0.41582 (7)	0.17787 (17)	0.58034 (11)	0.0460 (3)
C15	0.46477 (8)	0.1691 (2)	0.67378 (11)	0.0542 (4)
H15	0.4483	0.134	0.7366	0.065*
C16	0.53723 (8)	0.2105 (2)	0.67713 (10)	0.0519 (3)
H16	0.5687	0.2026	0.7413	0.062*
C17	0.33652 (8)	0.1382 (2)	0.57897 (12)	0.0567 (4)
H17A	0.3309	0.0088	0.6086	0.068*
H17B	0.3124	0.1373	0.5056	0.068*
C18	0.30012 (9)	0.2874 (2)	0.64108 (12)	0.0585 (4)
H18A	0.2503	0.2494	0.6416	0.07*
H18B	0.3245	0.2921	0.7143	0.07*
O19	0.30252 (6)	0.47658 (15)	0.59305 (8)	0.0582 (3)
H19	0.3042 (9)	0.563 (3)	0.6438 (15)	0.085 (6)*
O20	0.81964 (6)	0.73557 (16)	0.59742 (9)	0.0684 (3)
C21	0.85404 (10)	0.9101 (3)	0.57235 (14)	0.0816 (5)
H21A	0.8596	0.9967	0.6328	0.122*
H21B	0.8253	0.9731	0.5127	0.122*
H21C	0.9007	0.8792	0.5545	0.122*
O22	0.94077 (6)	0.27125 (18)	0.93408 (9)	0.0717 (3)
C23	0.90471 (10)	0.1000 (3)	0.96033 (14)	0.0786 (5)
H23A	0.8569	0.1336	0.9725	0.118*
H23B	0.931	0.0422	1.0237	0.118*
H23C	0.9017	0.0077	0.9026	0.118*

	U11	U22	U33	U12	U13	U23
C1	0.0455 (8)	0.0566 (8)	0.0415 (7)	−0.0014 (6)	0.0072 (6)	−0.0008 (6)
C2	0.0520 (9)	0.0562 (8)	0.0455 (7)	−0.0027 (7)	0.0075 (7)	0.0017 (6)
C3	0.0537 (9)	0.0628 (9)	0.0619 (9)	−0.0110 (7)	0.0099 (8)	−0.0016 (7)
C4	0.0474 (9)	0.0749 (10)	0.0567 (9)	−0.0025 (7)	0.0017 (7)	−0.0022 (8)
C5	0.0476 (8)	0.0672 (9)	0.0445 (7)	0.0075 (7)	0.0051 (6)	0.0014 (7)
C6	0.0512 (9)	0.0565 (8)	0.0468 (7)	−0.0010 (6)	0.0073 (7)	0.0019 (6)
N7	0.0557 (8)	0.0655 (8)	0.0434 (6)	−0.0115 (6)	−0.0001 (6)	0.0129 (6)
C8	0.0517 (8)	0.0435 (7)	0.0408 (7)	0.0000 (6)	0.0049 (6)	0.0041 (5)
O9	0.0631 (7)	0.0879 (8)	0.0550 (6)	−0.0102 (5)	0.0000 (5)	0.0303 (6)
N10	0.0527 (7)	0.0535 (6)	0.0381 (6)	−0.0037 (5)	0.0048 (5)	0.0070 (5)
C11	0.0501 (8)	0.0355 (6)	0.0400 (6)	0.0001 (5)	0.0053 (6)	−0.0010 (5)
C12	0.0579 (9)	0.0431 (7)	0.0368 (6)	0.0010 (6)	0.0062 (6)	0.0032 (5)
C13	0.0566 (9)	0.0420 (6)	0.0409 (7)	0.0016 (6)	−0.0017 (6)	−0.0002 (5)
C14	0.0530 (8)	0.0362 (6)	0.0482 (7)	−0.0004 (6)	0.0057 (6)	−0.0019 (5)
C15	0.0608 (10)	0.0614 (8)	0.0416 (7)	−0.0048 (7)	0.0118 (7)	0.0031 (6)
C16	0.0558 (9)	0.0613 (8)	0.0369 (7)	−0.0025 (7)	0.0012 (6)	0.0023 (6)
C17	0.0572 (9)	0.0500 (7)	0.0623 (9)	−0.0067 (7)	0.0070 (7)	0.0022 (7)
C18	0.0607 (10)	0.0674 (9)	0.0497 (8)	−0.0025 (7)	0.0154 (7)	0.0092 (7)
O19	0.0772 (7)	0.0569 (6)	0.0417 (5)	0.0039 (5)	0.0133 (5)	−0.0018 (5)
O20	0.0651 (7)	0.0690 (7)	0.0666 (7)	−0.0169 (5)	−0.0045 (6)	0.0212 (5)
C21	0.0899 (13)	0.0691 (10)	0.0816 (12)	−0.0219 (9)	0.0003 (10)	0.0213 (9)
O22	0.0582 (7)	0.0874 (8)	0.0647 (7)	0.0025 (6)	−0.0060 (5)	0.0186 (6)
C23	0.0776 (12)	0.0815 (12)	0.0741 (11)	0.0069 (9)	0.0035 (9)	0.0232 (10)

C1—C6	1.3875 (19)	C13—C14	1.3913 (18)
C1—C2	1.4000 (19)	C13—H13	0.93
C1—N7	1.4069 (18)	C14—C15	1.3835 (19)
C2—O20	1.3731 (17)	C14—C17	1.5090 (19)
C2—C3	1.375 (2)	C15—C16	1.382 (2)
C3—C4	1.381 (2)	C15—H15	0.93
C3—H3	0.93	C16—H16	0.93
C4—C5	1.378 (2)	C17—C18	1.512 (2)
C4—H4	0.93	C17—H17A	0.97
C5—O22	1.3787 (17)	C17—H17B	0.97
C5—C6	1.381 (2)	C18—O19	1.4286 (17)
C6—H6	0.93	C18—H18A	0.97
N7—C8	1.3677 (17)	C18—H18B	0.97
N7—H7	0.865 (15)	O19—H19	0.867 (18)
C8—O9	1.2226 (15)	O20—C21	1.4122 (18)
C8—N10	1.3528 (17)	C21—H21A	0.96
N10—C11	1.4159 (17)	C21—H21B	0.96
N10—H10	0.867 (14)	C21—H21C	0.96
C11—C12	1.3874 (19)	O22—C23	1.414 (2)
C11—C16	1.3878 (18)	C23—H23A	0.96
C12—C13	1.3764 (19)	C23—H23B	0.96
C12—H12	0.93	C23—H23C	0.96
C6—C1—C2	119.60 (13)	C15—C14—C13	116.99 (13)
C6—C1—N7	123.65 (13)	C15—C14—C17	121.59 (12)
C2—C1—N7	116.72 (12)	C13—C14—C17	121.42 (13)
O20—C2—C3	125.36 (13)	C16—C15—C14	122.41 (12)
O20—C2—C1	114.92 (12)	C16—C15—H15	118.8
C3—C2—C1	119.72 (13)	C14—C15—H15	118.8
C2—C3—C4	120.47 (14)	C15—C16—C11	119.71 (13)
C2—C3—H3	119.8	C15—C16—H16	120.1
C4—C3—H3	119.8	C11—C16—H16	120.1
C5—C4—C3	119.93 (14)	C14—C17—C18	113.43 (12)
C5—C4—H4	120	C14—C17—H17A	108.9
C3—C4—H4	120	C18—C17—H17A	108.9
C4—C5—O22	115.81 (13)	C14—C17—H17B	108.9
C4—C5—C6	120.46 (14)	C18—C17—H17B	108.9
O22—C5—C6	123.73 (14)	H17A—C17—H17B	107.7
C5—C6—C1	119.80 (13)	O19—C18—C17	109.69 (11)
C5—C6—H6	120.1	O19—C18—H18A	109.7
C1—C6—H6	120.1	C17—C18—H18A	109.7
C8—N7—C1	126.35 (11)	O19—C18—H18B	109.7
C8—N7—H7	115.6 (10)	C17—C18—H18B	109.7
C1—N7—H7	116.0 (10)	H18A—C18—H18B	108.2
O9—C8—N10	124.10 (13)	C18—O19—H19	107.0 (12)
O9—C8—N7	122.73 (13)	C2—O20—C21	117.91 (12)
N10—C8—N7	113.16 (11)	O20—C21—H21A	109.5
C8—N10—C11	128.33 (11)	O20—C21—H21B	109.5
C8—N10—H10	116.8 (9)	H21A—C21—H21B	109.5
C11—N10—H10	114.2 (9)	O20—C21—H21C	109.5
C12—C11—C16	118.65 (12)	H21A—C21—H21C	109.5
C12—C11—N10	116.99 (11)	H21B—C21—H21C	109.5
C16—C11—N10	124.31 (12)	C5—O22—C23	118.12 (12)
C13—C12—C11	120.76 (12)	O22—C23—H23A	109.5
C13—C12—H12	119.6	O22—C23—H23B	109.5
C11—C12—H12	119.6	H23A—C23—H23B	109.5
C12—C13—C14	121.44 (13)	O22—C23—H23C	109.5
C12—C13—H13	119.3	H23A—C23—H23C	109.5
C14—C13—H13	119.3	H23B—C23—H23C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N7—H7···O20	0.865 (15)	2.227 (14)	2.6113 (16)	106.7 (11)
O19—H19···O9i	0.867 (18)	1.841 (19)	2.7080 (14)	178.0 (17)
N10—H10···O19ii	0.867 (14)	2.161 (14)	2.9799 (15)	157.4 (12)
N7—H7···O19ii	0.865 (15)	2.189 (15)	2.9837 (15)	152.6 (13)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N7—H7⋯O20	0.865 (15)	2.227 (14)	2.6113 (16)	106.7 (11)
O19—H19⋯O9i	0.867 (18)	1.841 (19)	2.7080 (14)	178.0 (17)
N10—H10⋯O19ii	0.867 (14)	2.161 (14)	2.9799 (15)	157.4 (12)
N7—H7⋯O19ii	0.865 (15)	2.189 (15)	2.9837 (15)	152.6 (13)

Symmetry codes: (i) ; (ii) .