Methyl 2-[(tert-but­oxy­carbon­yl)amino]-3-(3-methyl-2-sulfanyl­idene-2,3-dihydro-1H-imidazol-1-yl)propano­ate

Chan, C.-F.; Guo, Y.-C.; Huang, B.-H.; Chen, M.-J.

doi:10.1107/S1600536812043486

Volume 68
Part 11
Page o3206
November 2012

Received 12 October 2012
Accepted 19 October 2012
Online 24 October 2012

Key indicators
Single-crystal X-ray study
T = 110 K
Mean (C-C) = 0.002 Å
R = 0.036
wR = 0.137
Data-to-parameter ratio = 16.3
Details

Methyl 2-[(tert-butoxycarbonyl)amino]-3-(3-methyl-2-sulfanylidene-2,3-dihydro-1H-imidazol-1-yl)propanoate

Chin-Feng Chan,^a Yi-Cin Guo,^a Bor-Hunn Huang ^b and Ming-Jen Chen ^a ^*

^aDepartment of Applied Cosmetology and Graduate Institute of Cosmetic Science, Hungkuang University, Taichung 433, Taiwan, and ^bDepartment of Chemistry, National Chung Hsing University, Taichung 402, Taiwan
Correspondence e-mail: mjchen@sunrise.hk.edu.tw

In the title compound, C₁₃H₂₁N₃O₄S, the mean plane of the -N(H)-C(=O)-O- group of the carbamate unit forms a dihedral angle of 64.7 (2)° with the mean plane of the -C-C(=O)-O- group of the ester unit. In the crystal, molecules are linked by N-HO=C hydrogen bonds, forming chains along the c-axis direction.

Related literature

The title compound is a mercaptoimidazole derivative. For applications of mercaptoimidazole derivatives in the treatment of hyperpigmentation, see: Kasraee (2002); Kasraee et al. (2005) and for inhibiting tyrosinase, see: Liao et al. (2012). For typical bond lengths of intermolecular N-HO=C hydrogen bonds, see: Taylor et al. (1984).

Experimental

Crystal data

C₁₃H₂₁N₃O₄S
M_r = 315.39
Monoclinic, P 2₁ /c
a = 8.7636 (1) Å
b = 19.1184 (2) Å
c = 9.6735 (2) Å
= 98.485 (1)°
V = 1603.02 (4) Å³
Z = 4
Cu K radiation
= 1.97 mm^-1
T = 110 K
0.60 × 0.50 × 0.30 mm

Data collection

Agilent Xcalibur (Sapphire3, Gemini) diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010) T_min = 0.550, T_max = 1.000
12262 measured reflections
3093 independent reflections
2923 reflections with I > 2(I)
R_int = 0.019

Refinement

R[F² > 2(F²)] = 0.036
wR(F²) = 0.137
S = 1.05
3093 reflections
190 parameters
H-atom parameters constrained
_max = 0.39 e Å^-3
_min = -0.53 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N3-H3AO1ⁱ	0.88	2.25	2.9819 (14)	140
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5544 ).

Acknowledgements

We gratefully acknowledge financial support in part from the National Science Council, Taiwan (NSC 99-2119-M-241-001-MY2). Helpful comments from the reviewers are also greatly appreciated.

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Kasraee, B. (2002). J. Invest. Dermatol. 118, 205-207.
Kasraee, B., Handjani, F., Parhizgar, A., Omrani, G. R., Fallahi, M. R., Amini, M., Nikbakhsh, M., Tran, C., Hügin, A., Sorg, O. & Saurat, J.-H. (2005). Dermatology, 211, 360-362.
Liao, W. C., Wu, W. H., Tsai, P.-C., Wang, H.-F., Liu, Y.-H. & Chan, C.-F. (2012). Appl. Biochem. Biotechnol. 166, 259-267.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Taylor, R., Kennard, O. & Versichel, W. (1984). Acta Cryst. B40, 280-288.

organic compounds