1-(2,5-Dimeth-oxy-phen-yl)-3-(2-hy-droxy-eth-yl)urea.

In the title compound, C(11)H(16)N(2)O(4), the 2,5-dimeth-oxy-phenyl moiety is almost planar, with an r.m.s. deviation of 0.026 Å. The dihedral angle between the benzene ring and the plane of the urea moiety is 13.86 (5)°. 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, see: Francisco et al. (2006 ▶); Jimenez et al. (2001 ▶); Korner & Pawelek (1982 ▶); Urabe et al. (1998 ▶). For the development of potent inhibitory agents of tyrosinase and melanin formation as whitening agents, see: Battaini et al. (2000 ▶); Cabanes et al. (1994 ▶); Choi et al. (2010 ▶); Germanas et al. (2007 ▶); Hong et al. (2008 ▶); Kwak et al. (2010 ▶); Lemic-Stojcevic et al. (1995 ▶); Lee et al. (2007 ▶); Liangli (2003 ▶); Thanigaimalai et al. (2010 ▶); Yi et al. (2009 ▶, 2010 ▶).

Experimental

Crystal data

C11H16N2O4

M = 240.26

Monoclinic,

a = 10.8571 (9) Å

b = 11.5559 (10) Å

c = 9.9337 (8) Å

β = 109.514 (4)°

V = 1174.73 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 173 K

0.21 × 0.18 × 0.09 mm

Data collection

Bruker SMART CCD area-detector diffractometer

9411 measured reflections

2352 independent reflections

1982 reflections with I > 2σ(I)

R int = 0.062

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.090

S = 1.07

2352 reflections

168 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.25 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 ▶) and DIAMOND (Brandenburg, 2010 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810028436/jh2184sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810028436/jh2184Isup2.hkl

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

C11H16N2O4	F(000) = 512
Mr = 240.26	Dx = 1.358 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4246 reflections
a = 10.8571 (9) Å	θ = 2.8–28.2°
b = 11.5559 (10) Å	µ = 0.10 mm−1
c = 9.9337 (8) Å	T = 173 K
β = 109.514 (4)°	Block, colourless
V = 1174.73 (17) Å3	0.21 × 0.18 × 0.09 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	Rint = 0.062
φ and ω scans	θmax = 26.5°, θmin = 2.7°
9411 measured reflections	h = −6→13
2352 independent reflections	k = −14→9
1982 reflections with I > 2σ(I)	l = −12→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)] = 0.034	w = 1/[σ2(Fo2) + (0.0526P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.090	(Δ/σ)max < 0.001
S = 1.07	Δρmax = 0.19 e Å−3
2352 reflections	Δρmin = −0.25 e Å−3
168 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	0.26322 (10)	0.50237 (9)	0.48181 (12)	0.0208 (2)
C2	0.15431 (11)	0.43224 (9)	0.47055 (12)	0.0220 (3)
C3	0.05312 (11)	0.42372 (9)	0.34222 (12)	0.0252 (3)
H3	−0.019	0.3778	0.3357	0.03*
C4	0.05831 (11)	0.48333 (9)	0.22288 (13)	0.0264 (3)
H4	−0.0101	0.4778	0.1366	0.032*
C5	0.16604 (11)	0.55102 (9)	0.23333 (12)	0.0242 (3)
C6	0.26888 (11)	0.56150 (9)	0.36195 (12)	0.0228 (3)
H6	0.3407	0.6076	0.3677	0.027*
N7	0.36023 (9)	0.50709 (8)	0.61700 (10)	0.0234 (2)
H7	0.3458 (12)	0.4616 (12)	0.6799 (15)	0.035 (4)*
C8	0.45894 (10)	0.58708 (9)	0.66522 (12)	0.0205 (2)
O9	0.48440 (8)	0.65994 (6)	0.58761 (8)	0.0260 (2)
N10	0.52601 (9)	0.57919 (8)	0.80586 (11)	0.0250 (2)
H10	0.5012 (13)	0.5293 (11)	0.8553 (15)	0.033 (3)*
C11	0.62695 (11)	0.66229 (10)	0.87792 (12)	0.0268 (3)
H11A	0.5892	0.7391	0.8696	0.032*
H11B	0.6936	0.6631	0.8329	0.032*
C12	0.68773 (11)	0.63093 (10)	1.03317 (13)	0.0271 (3)
H12A	0.7315	0.5568	1.0407	0.032*
H12B	0.7531	0.6884	1.0801	0.032*
O13	0.59367 (8)	0.62435 (7)	1.10450 (9)	0.0260 (2)
H13	0.5628 (15)	0.6954 (15)	1.1048 (16)	0.054 (5)*
O14	0.15906 (8)	0.37701 (6)	0.59484 (9)	0.0274 (2)
C15	0.05328 (12)	0.30175 (10)	0.58780 (14)	0.0312 (3)
H15A	−0.0265	0.3454	0.5619	0.047*
H15B	0.0686	0.2662	0.6793	0.047*
H15C	0.0465	0.2429	0.5175	0.047*
O16	0.16393 (8)	0.60560 (7)	0.10891 (9)	0.0329 (2)
C17	0.26678 (12)	0.68455 (11)	0.11745 (14)	0.0343 (3)
H17A	0.267	0.7454	0.1833	0.051*
H17B	0.2539	0.717	0.0248	0.051*
H17C	0.3489	0.6445	0.15	0.051*

	U11	U22	U33	U12	U13	U23
C1	0.0197 (5)	0.0189 (5)	0.0216 (6)	0.0014 (4)	0.0039 (5)	−0.0032 (4)
C2	0.0235 (6)	0.0185 (5)	0.0240 (6)	0.0011 (4)	0.0078 (5)	−0.0006 (4)
C3	0.0214 (6)	0.0238 (6)	0.0283 (7)	−0.0040 (5)	0.0057 (5)	−0.0044 (5)
C4	0.0232 (6)	0.0288 (6)	0.0226 (7)	−0.0007 (5)	0.0013 (5)	−0.0040 (5)
C5	0.0259 (6)	0.0244 (6)	0.0207 (6)	0.0029 (5)	0.0058 (5)	−0.0004 (4)
C6	0.0213 (6)	0.0227 (5)	0.0234 (6)	−0.0017 (4)	0.0063 (5)	−0.0010 (5)
N7	0.0239 (5)	0.0238 (5)	0.0197 (5)	−0.0049 (4)	0.0034 (5)	0.0027 (4)
C8	0.0192 (6)	0.0200 (5)	0.0215 (6)	0.0012 (4)	0.0058 (5)	−0.0016 (4)
O9	0.0280 (5)	0.0256 (4)	0.0225 (5)	−0.0062 (3)	0.0061 (4)	0.0023 (3)
N10	0.0258 (5)	0.0261 (5)	0.0200 (6)	−0.0075 (4)	0.0034 (5)	0.0014 (4)
C11	0.0240 (6)	0.0309 (6)	0.0237 (7)	−0.0082 (5)	0.0054 (5)	−0.0030 (5)
C12	0.0223 (6)	0.0321 (6)	0.0241 (7)	−0.0023 (5)	0.0042 (5)	−0.0035 (5)
O13	0.0307 (5)	0.0228 (4)	0.0247 (5)	−0.0005 (3)	0.0095 (4)	0.0010 (3)
O14	0.0259 (4)	0.0278 (4)	0.0264 (5)	−0.0069 (3)	0.0060 (4)	0.0041 (3)
C15	0.0289 (6)	0.0268 (6)	0.0378 (7)	−0.0076 (5)	0.0111 (6)	0.0028 (5)
O16	0.0316 (5)	0.0406 (5)	0.0220 (5)	−0.0059 (4)	0.0031 (4)	0.0058 (4)
C17	0.0330 (7)	0.0360 (7)	0.0326 (7)	−0.0024 (5)	0.0092 (6)	0.0094 (6)

C1—C6	1.3918 (15)	N10—H10	0.856 (14)
C1—N7	1.4039 (15)	C11—C12	1.5051 (16)
C1—C2	1.4068 (15)	C11—H11A	0.97
C2—O14	1.3754 (13)	C11—H11B	0.97
C2—C3	1.3806 (17)	C12—O13	1.4262 (13)
C3—C4	1.3883 (16)	C12—H12A	0.97
C3—H3	0.93	C12—H12B	0.97
C4—C5	1.3819 (16)	O13—H13	0.887 (17)
C4—H4	0.93	O14—C15	1.4236 (13)
C5—O16	1.3809 (13)	C15—H15A	0.96
C5—C6	1.3931 (17)	C15—H15B	0.96
C6—H6	0.93	C15—H15C	0.96
N7—C8	1.3746 (14)	O16—C17	1.4224 (14)
N7—H7	0.870 (14)	C17—H17A	0.96
C8—O9	1.2337 (12)	C17—H17B	0.96
C8—N10	1.3457 (15)	C17—H17C	0.96
N10—C11	1.4531 (14)
C6—C1—N7	124.46 (10)	N10—C11—C12	110.24 (9)
C6—C1—C2	119.40 (10)	N10—C11—H11A	109.6
N7—C1—C2	116.14 (10)	C12—C11—H11A	109.6
O14—C2—C3	125.13 (9)	N10—C11—H11B	109.6
O14—C2—C1	114.68 (10)	C12—C11—H11B	109.6
C3—C2—C1	120.19 (10)	H11A—C11—H11B	108.1
C2—C3—C4	120.42 (10)	O13—C12—C11	112.35 (10)
C2—C3—H3	119.8	O13—C12—H12A	109.1
C4—C3—H3	119.8	C11—C12—H12A	109.1
C5—C4—C3	119.44 (11)	O13—C12—H12B	109.1
C5—C4—H4	120.3	C11—C12—H12B	109.1
C3—C4—H4	120.3	H12A—C12—H12B	107.9
O16—C5—C4	115.51 (10)	C12—O13—H13	106.6 (10)
O16—C5—C6	123.35 (10)	C2—O14—C15	116.85 (9)
C4—C5—C6	121.13 (10)	O14—C15—H15A	109.5
C1—C6—C5	119.41 (10)	O14—C15—H15B	109.5
C1—C6—H6	120.3	H15A—C15—H15B	109.5
C5—C6—H6	120.3	O14—C15—H15C	109.5
C8—N7—C1	127.44 (9)	H15A—C15—H15C	109.5
C8—N7—H7	117.6 (9)	H15B—C15—H15C	109.5
C1—N7—H7	114.0 (9)	C5—O16—C17	117.49 (9)
O9—C8—N10	122.59 (10)	O16—C17—H17A	109.5
O9—C8—N7	123.54 (10)	O16—C17—H17B	109.5
N10—C8—N7	113.87 (9)	H17A—C17—H17B	109.5
C8—N10—C11	121.61 (9)	O16—C17—H17C	109.5
C8—N10—H10	118.4 (9)	H17A—C17—H17C	109.5
C11—N10—H10	119.5 (9)	H17B—C17—H17C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N7—H7···O14	0.870 (14)	2.153 (13)	2.5995 (12)	111.4 (11)
N7—H7···O13i	0.870 (14)	2.251 (14)	3.0473 (13)	152.3 (12)
N10—H10···O13i	0.856 (14)	2.156 (14)	2.9642 (12)	157.1 (12)
O13—H13···O9ii	0.887 (17)	1.858 (18)	2.7417 (11)	174.0 (15)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N7—H7⋯O14	0.870 (14)	2.153 (13)	2.5995 (12)	111.4 (11)
N7—H7⋯O13i	0.870 (14)	2.251 (14)	3.0473 (13)	152.3 (12)
N10—H10⋯O13i	0.856 (14)	2.156 (14)	2.9642 (12)	157.1 (12)
O13—H13⋯O9ii	0.887 (17)	1.858 (18)	2.7417 (11)	174.0 (15)

Symmetry codes: (i) ; (ii) .