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

In the title compound, C(10)H(14)N(2)O(3)S, the 3-meth-oxy-phenyl unit is almost planar, with an r.m.s. deviation of 0.013 Å. The dihedral angle between the benzene ring and the plane of the thio-urea unit is 62.57 (4)°. In the crystal, N-H⋯O and O-H⋯S hydrogen bonds link the mol-ecules into a three-dimensional network.

Related literature

For general background to melanin, see: Ha et al. (2007 ▶). For the development of potent inhibitory agents of tyrosinase, see: Kojima et al. (1995 ▶); Cabanes et al. (1994 ▶); Casanola-Martin et al. (2006 ▶); Son et al. (2000 ▶); Iida et al. (1995 ▶). For thio­urea derivatives, see: Thanigaimalai et al. (2010 ▶); Klabunde et al. (1998 ▶); Criton (2006 ▶); Daniel (2006 ▶); Yi et al. (2009 ▶); Liu et al. (2009 ▶).

Experimental

Crystal data

C10H14N2O2S

M = 226.29

Monoclinic,

a = 10.9894 (3) Å

b = 8.0759 (2) Å

c = 12.8067 (4) Å

β = 102.920 (1)°

V = 1107.81 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 296 K

0.37 × 0.21 × 0.2 mm

Data collection

Bruker SMART CCD area-detector diffractometer

8965 measured reflections

2478 independent reflections

2013 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.107

S = 1.08

2478 reflections

148 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.36 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/S1600536810034665/tk2706sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810034665/tk2706Isup2.hkl

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

C10H14N2O2S	F(000) = 480
Mr = 226.29	Dx = 1.357 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4441 reflections
a = 10.9894 (3) Å	θ = 2.8–28.1°
b = 8.0759 (2) Å	µ = 0.27 mm−1
c = 12.8067 (4) Å	T = 296 K
β = 102.920 (1)°	Block, colorless
V = 1107.81 (5) Å3	0.37 × 0.21 × 0.2 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	Rint = 0.059
φ and ω scans	θmax = 27.5°, θmin = 2.2°
8965 measured reflections	h = −10→14
2478 independent reflections	k = −4→10
2013 reflections with I > 2σ(I)	l = −15→15

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) + (0.0621P)2 + 0.0837P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.107	(Δ/σ)max = 0.001
S = 1.08	Δρmax = 0.22 e Å−3
2478 reflections	Δρmin = −0.36 e Å−3
148 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	0.47197 (11)	0.63459 (15)	0.77190 (10)	0.0330 (3)
C2	0.46149 (11)	0.49103 (15)	0.83014 (10)	0.0330 (3)
H2	0.5124	0.4001	0.8268	0.04*
C3	0.37377 (11)	0.48652 (16)	0.89296 (10)	0.0350 (3)
C4	0.29844 (13)	0.62354 (19)	0.89796 (13)	0.0463 (4)
H4	0.2409	0.621	0.9413	0.056*
C5	0.30915 (14)	0.7629 (2)	0.83859 (14)	0.0532 (4)
H5	0.2576	0.8534	0.8412	0.064*
C6	0.39582 (13)	0.76975 (19)	0.77507 (13)	0.0464 (4)
H6	0.4027	0.864	0.7351	0.056*
N7	0.55784 (11)	0.64047 (14)	0.70312 (10)	0.0377 (3)
H7	0.5267 (16)	0.658 (2)	0.6393 (16)	0.051 (5)*
C8	0.68277 (12)	0.62256 (14)	0.73143 (11)	0.0341 (3)
S9	0.76633 (4)	0.61967 (5)	0.63478 (3)	0.05057 (15)
N10	0.73496 (11)	0.60801 (14)	0.83569 (10)	0.0364 (3)
H10	0.6920 (16)	0.6201 (17)	0.8796 (14)	0.040 (4)*
C11	0.86769 (12)	0.57980 (18)	0.87843 (13)	0.0426 (3)
H11A	0.9014	0.5185	0.8262	0.051*
H11B	0.8782	0.5124	0.9425	0.051*
C12	0.94037 (12)	0.73800 (18)	0.90533 (12)	0.0443 (3)
H12A	1.0289	0.7127	0.9243	0.053*
H12B	0.9253	0.8091	0.8427	0.053*
O13	0.90658 (11)	0.82309 (17)	0.99133 (9)	0.0553 (3)
H13	0.865 (2)	0.906 (3)	0.973 (2)	0.092 (8)*
O14	0.35374 (10)	0.35339 (12)	0.95322 (9)	0.0469 (3)
C15	0.40934 (16)	0.1998 (2)	0.93648 (14)	0.0546 (4)
H15A	0.3879	0.1178	0.9836	0.082*
H15B	0.4984	0.2123	0.9511	0.082*
H15C	0.3793	0.1655	0.8635	0.082*

	U11	U22	U33	U12	U13	U23
C1	0.0284 (6)	0.0451 (7)	0.0251 (7)	−0.0024 (5)	0.0048 (5)	0.0000 (5)
C2	0.0314 (6)	0.0387 (6)	0.0299 (7)	−0.0006 (5)	0.0092 (5)	−0.0023 (5)
C3	0.0319 (6)	0.0455 (7)	0.0283 (7)	−0.0063 (5)	0.0079 (5)	−0.0037 (5)
C4	0.0348 (7)	0.0624 (9)	0.0460 (9)	0.0024 (6)	0.0182 (6)	−0.0052 (6)
C5	0.0439 (8)	0.0553 (9)	0.0624 (11)	0.0153 (7)	0.0162 (7)	0.0019 (7)
C6	0.0431 (7)	0.0482 (7)	0.0479 (9)	0.0066 (6)	0.0099 (6)	0.0096 (6)
N7	0.0354 (6)	0.0528 (7)	0.0256 (7)	−0.0022 (5)	0.0084 (5)	0.0063 (5)
C8	0.0372 (7)	0.0328 (6)	0.0348 (8)	−0.0040 (5)	0.0134 (6)	0.0013 (5)
S9	0.0494 (2)	0.0667 (3)	0.0431 (3)	−0.01090 (17)	0.02646 (18)	−0.00218 (16)
N10	0.0307 (5)	0.0481 (6)	0.0321 (7)	−0.0006 (4)	0.0105 (5)	0.0030 (5)
C11	0.0339 (7)	0.0469 (7)	0.0472 (9)	0.0064 (5)	0.0092 (6)	0.0105 (6)
C12	0.0313 (6)	0.0598 (8)	0.0420 (8)	−0.0017 (6)	0.0089 (6)	0.0081 (6)
O13	0.0546 (7)	0.0724 (8)	0.0347 (6)	−0.0015 (6)	0.0011 (5)	−0.0046 (5)
O14	0.0517 (6)	0.0520 (6)	0.0440 (6)	−0.0067 (4)	0.0255 (5)	0.0017 (4)
C15	0.0634 (10)	0.0484 (8)	0.0561 (11)	−0.0017 (7)	0.0223 (8)	0.0085 (7)

C1—C6	1.3815 (18)	C8—S9	1.6983 (14)
C1—C2	1.3972 (17)	N10—C11	1.4567 (17)
C1—N7	1.4284 (18)	N10—H10	0.817 (19)
C2—C3	1.3874 (18)	C11—C12	1.505 (2)
C2—H2	0.93	C11—H11A	0.97
C3—O14	1.3696 (16)	C11—H11B	0.97
C3—C4	1.392 (2)	C12—O13	1.4163 (19)
C4—C5	1.378 (2)	C12—H12A	0.97
C4—H4	0.93	C12—H12B	0.97
C5—C6	1.385 (2)	O13—H13	0.81 (2)
C5—H5	0.93	O14—C15	1.4200 (19)
C6—H6	0.93	C15—H15A	0.96
N7—C8	1.3471 (17)	C15—H15B	0.96
N7—H7	0.824 (19)	C15—H15C	0.96
C8—N10	1.3353 (18)
C6—C1—C2	121.14 (12)	C8—N10—C11	124.03 (13)
C6—C1—N7	118.68 (12)	C8—N10—H10	119.6 (12)
C2—C1—N7	120.10 (11)	C11—N10—H10	116.3 (12)
C3—C2—C1	118.83 (11)	N10—C11—C12	112.87 (11)
C3—C2—H2	120.6	N10—C11—H11A	109
C1—C2—H2	120.6	C12—C11—H11A	109
O14—C3—C2	124.57 (12)	N10—C11—H11B	109
O14—C3—C4	115.21 (12)	C12—C11—H11B	109
C2—C3—C4	120.22 (13)	H11A—C11—H11B	107.8
C5—C4—C3	119.92 (14)	O13—C12—C11	111.83 (12)
C5—C4—H4	120	O13—C12—H12A	109.2
C3—C4—H4	120	C11—C12—H12A	109.2
C4—C5—C6	120.77 (14)	O13—C12—H12B	109.2
C4—C5—H5	119.6	C11—C12—H12B	109.2
C6—C5—H5	119.6	H12A—C12—H12B	107.9
C1—C6—C5	119.10 (14)	C12—O13—H13	113.9 (18)
C1—C6—H6	120.5	C3—O14—C15	118.15 (11)
C5—C6—H6	120.5	O14—C15—H15A	109.5
C8—N7—C1	127.20 (12)	O14—C15—H15B	109.5
C8—N7—H7	117.2 (13)	H15A—C15—H15B	109.5
C1—N7—H7	115.6 (13)	O14—C15—H15C	109.5
N10—C8—N7	117.55 (13)	H15A—C15—H15C	109.5
N10—C8—S9	123.11 (10)	H15B—C15—H15C	109.5
N7—C8—S9	119.34 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N7—H7···O13i	0.824 (19)	2.059 (19)	2.8619 (16)	164.6 (17)
N10—H10···O14ii	0.817 (19)	2.316 (19)	3.0877 (17)	157.8 (15)
O13—H13···S9iii	0.81 (2)	2.47 (2)	3.2532 (14)	163 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N7—H7⋯O13i	0.824 (19)	2.059 (19)	2.8619 (16)	164.6 (17)
N10—H10⋯O14ii	0.817 (19)	2.316 (19)	3.0877 (17)	157.8 (15)
O13—H13⋯S9iii	0.81 (2)	2.47 (2)	3.2532 (14)	163 (2)

Symmetry codes: (i) ; (ii) ; (iii) .