1-[3-(Hy­droxy­meth­yl)phen­yl]-3-phenyl­urea

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

doi:10.1107/S1600536811028315

Volume 67
Part 8
Page o2094
August 2011

Received 8 July 2011
Accepted 14 July 2011
Online 23 July 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.002 Å
R = 0.041
wR = 0.111
Data-to-parameter ratio = 15.4
Details

1-[3-(Hydroxymethyl)phenyl]-3-phenylurea

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, C₁₄H₁₄N₂O₂, the dihedral angle between the benzene rings is 23.6 (1)°. 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 three-dimensional network.

Related literature

For general background to melanin, see: Kubo et al. (2000); Claus & Decker (2006). For the development of tyrosinase inhibitors, see: Khan et al. (2006); Kojima et al. (1995); Cabanes et al. (1994); Casañola-Martin et al. (2006); Son et al. (2000); Hong et al. (2008); Lee et al. (2007); Yi et al. (2010); Choi et al. (2010).

Experimental

Crystal data

C₁₄H₁₄N₂O₂
M_r = 242.27
Monoclinic, P 2₁ /c
a = 14.6207 (8) Å
b = 7.0692 (4) Å
c = 12.4019 (5) Å
= 109.818 (3)°
V = 1205.90 (11) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 296 K
0.22 × 0.21 × 0.05 mm

Data collection

Bruker SMART CCD area-detector diffractometer
9960 measured reflections
2694 independent reflections
1664 reflections with I > 2(I)
R_int = 0.052

Refinement

R[F² > 2(F²)] = 0.041
wR(F²) = 0.111
S = 0.93
2694 reflections
175 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.14 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N7-H7O18ⁱ	0.87 (2)	2.12 (2)	2.958 (2)	163 (1)
N10-H10O18ⁱ	0.90 (2)	2.18 (2)	3.031 (2)	157 (1)
O18-H18O9ⁱⁱ	0.86 (2)	1.91 (2)	2.763 (2)	175 (2)
Symmetry codes: (i) -x+1, -y+1, -z; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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: ORTEP-3 for Windows (Farrugia, 1997); 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: IM2305 ).

Acknowledgements

This work was undertaked 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). Also, we wish to thank the DBIO company for partial support of this work.

References

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Casañola-Martin, G. M., Khan, M. T. H., Marrero-Ponce, Y., Ather, A., Sultankhodzhaev, F. & Torrens, F. (2006). Bioorg. Med. Chem. Lett. 16, 324-330.
Choi, H., Lee, T., Han, B. H., Kang, S. K. & Sung, C. K. (2010). Acta Cryst. E66, o2088-o2089.
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organic compounds