1-(2-Hy­droxy­eth­yl)-3-(3-meth­oxy­phen­yl)thio­urea

Choi, H.; Shim, Y.S.; Han, B.H.; Kang, S.K.; Sung, C.K.

doi:10.1107/S1600536810034665

Volume 66
Part 10
Pages o2487-o2488
October 2010

Received 24 August 2010
Accepted 28 August 2010
Online 4 September 2010

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.002 Å
R = 0.038
wR = 0.107
Data-to-parameter ratio = 16.7
Details

1-(2-Hydroxyethyl)-3-(3-methoxyphenyl)thiourea

Hyeong Choi,^a Yong Suk Shim,^a Byung Hee Han,^a Sung Kwon Kang ^a ^* and Chang Keun Sung ^b

^aDepartment of Chemistry, Chungnam National University, Daejeon 305-764, Republic of Korea, and ^bDepartment of Food Science and Technology, Chungnam National University, Daejeon 305-764, Republic of Korea
Correspondence e-mail: skkang@cnu.ac.kr

In the title compound, C₁₀H₁₄N₂O₃S, the 3-methoxyphenyl 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 thiourea unit is 62.57 (4)°. In the crystal, N-HO and O-HS hydrogen bonds link the molecules 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_r = 226.29
Monoclinic, P 2₁ /n
a = 10.9894 (3) Å
b = 8.0759 (2) Å
c = 12.8067 (4) Å
= 102.920 (1)°
V = 1107.81 (5) Å³
Z = 4
Mo K radiation
= 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 > 2(I)
R_int = 0.059

Refinement

R[F² > 2(F²)] = 0.038
wR(F²) = 0.107
S = 1.08
2478 reflections
148 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.22 e Å^-3
_min = -0.36 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N7-H7O13ⁱ	0.824 (19)	2.059 (19)	2.8619 (16)	164.6 (17)
N10-H10O14ⁱⁱ	0.817 (19)	2.316 (19)	3.0877 (17)	157.8 (15)
O13-H13S9ⁱⁱⁱ	0.81 (2)	2.47 (2)	3.2532 (14)	163 (2)
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z+2; (iii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2706 ).

Acknowledgements

This work is the result of a study performed under the "Human Resource Development Center for Economic Region Leading Industry" Project, supported by the Ministry of Education, Science & Technology (MEST) and the National Research Foundation of Korea (NRF).

References

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organic compounds