1-(2-Hy­droxy-2-phenyl­eth­yl)-3-(4-meth­oxy­phen­yl)urea

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

doi:10.1107/S1600536811036464

Volume 67
Part 10
Page o2632
October 2011

Received 30 August 2011
Accepted 7 September 2011
Online 14 September 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.007 Å
R = 0.060
wR = 0.166
Data-to-parameter ratio = 9.7
Details

1-(2-Hydroxy-2-phenylethyl)-3-(4-methoxyphenyl)urea

Hyeong Choi,^a Yong Suk Shim,^a Sung Chun Lee,^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, C₁₆H₁₈N₂O₃, the dihedral angle between the 4-methoxyphenyl ring and the urea group is 35.6 (2) °. The H atoms of the urea NH groups are positioned syn to each other. In the crystal, intermolecular N-HO and O-HO hydrogen bonds link the molecules into a two-dimensional array in the ac plane; the carbonyl-O atom is trifurcated.

Related literature

For general background to melanin, see: Prota (1988). For the development of potent inhibitory agents of tyrosinase, see: Khan et al. (2006); Kojima et al. (1995); Cabanes et al. (1994); Son et al. (2000); Iida et al. (1995).

Experimental

Crystal data

C₁₆H₁₈N₂O₃
M_r = 286.32
Monoclinic, P 2₁
a = 6.8120 (6) Å
b = 8.7659 (7) Å
c = 12.1393 (10) Å
= 97.009 (3)°
V = 719.46 (10) Å³
Z = 2
Mo K radiation
= 0.09 mm^-1
T = 296 K
0.07 × 0.05 × 0.03 mm

Data collection

Bruker SMART CCD area-detector diffractometer
5017 measured reflections
1947 independent reflections
1782 reflections with I > 2(I)
R_int = 0.073

Refinement

R[F² > 2(F²)] = 0.060
wR(F²) = 0.166
S = 1.05
1947 reflections
201 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.71 e Å^-3
_min = -0.26 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O8-H8O12ⁱ	0.86 (7)	2.09 (7)	2.863 (5)	150 (6)
N10-H10O12ⁱⁱ	0.81 (6)	2.35 (6)	3.098 (5)	153 (5)
N13-H13O12ⁱⁱ	0.79 (5)	2.14 (5)	2.898 (5)	161 (4)
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z]$ ; (ii) $[-x+2, y+{\script{1\over 2}}, -z]$ .

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); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2785 ).

Acknowledgements

We wish to thank the DBIO company for partial support of this work.

References

Bruker (2002). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Cabanes, J., Chazarra, S. & Garcia-Carmona, F. (1994). J. Pharm. Pharmacol. 46, 982-985.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Iida, K., Hase, K., Shimomura, K., Sudo, S. & Kadota, S. (1995). Planta Med. 61, 425-428.
Khan, K. M., Mughal, U. R., Khan, M. T. H., Perveen, S., Ullah, Z. & Choudhary, M. I. (2006). Bioorg. Med. Chem. 14, 344-351.
Kojima, S., Yamaguch, K., Morita, K., Ueno, Y. & Paolo, R. (1995). Biol. Pharm. Bull. 18, 1076-1080.
Prota, G. (1988). Med. Res. Rev. 8, 525-556.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Son, S. M., Moon, K. D. & Lee, C. Y. (2000). J. Agric. Food Chem. 48, 2071-2074.

organic compounds