N-(2,5-Dimeth­oxy­phen­yl)-N′-[4-(2-hy­droxy­eth­yl)phen­yl]urea

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

doi:10.1107/S1600536810033520

Volume 66
Part 9
Pages o2388-o2389
September 2010

Received 17 August 2010
Accepted 19 August 2010
Online 25 August 2010

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.002 Å
R = 0.038
wR = 0.108
Data-to-parameter ratio = 16.0
Details

N-(2,5-Dimethoxyphenyl)-N'-[4-(2-hydroxyethyl)phenyl]urea

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, C₁₇H₂₀N₂O₄, the 2,5-dimethoxyphenyl unit is essentially planar, with an r.m.s. deviation of 0.015 Å. The dihedral angle between the benzene rings is 43.66 (4)°. The molecular structure is stabilized by a short intramolecular N-HO hydrogen bond. 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 synthesis, melanogenesis and tyrosinase, see: Francisco et al. (2006); Hearing & Jimenez (1987); Prota (1988); Grimes et al. (2006); Maeda & Fukuda (1991). For the development of potent inhibitory agents of tyrosinase and melanin formation as whitening agents, see: Ohguchi et al. (2003); Lemic-Stojcevic et al. (1995); Battaini et al. (2000); Cabanes et al. (1994); Liangli (2003); Thanigaimalai et al. (2010); Hong et al. (2008); Lee et al. (2007); Yi et al. (2009, 2010); Kwak et al. (2010); Choi et al. (2010); Germanas et al. (2007); Briganti et al. (2003).

Experimental

Crystal data

C₁₇H₂₀N₂O₄
M_r = 316.35
Monoclinic, P 2₁ /c
a = 18.7551 (18) Å
b = 6.8095 (6) Å
c = 12.6881 (12) Å
= 98.930 (3)°
V = 1600.8 (3) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 296 K
0.31 × 0.28 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer
13398 measured reflections
3563 independent reflections
2473 reflections with I > 2(I)
R_int = 0.045

Refinement

R[F² > 2(F²)] = 0.038
wR(F²) = 0.108
S = 1.03
3563 reflections
222 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.15 e Å^-3
_min = -0.16 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N7-H7O20	0.865 (15)	2.227 (14)	2.6113 (16)	106.7 (11)
O19-H19O9ⁱ	0.867 (18)	1.841 (19)	2.7080 (14)	178.0 (17)
N10-H10O19ⁱⁱ	0.867 (14)	2.161 (14)	2.9799 (15)	157.4 (12)
N7-H7O19ⁱⁱ	0.865 (15)	2.189 (15)	2.9837 (15)	152.6 (13)
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) -x+1, -y+1, -z+1.

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: VM2041 ).

Acknowledgements

This work is the result of a study on 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