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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 [sigma](C-C) = 0.002 Å
R = 0.036
wR = 0.137
Data-to-parameter ratio = 16.3
Details
Open access

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

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-H...O=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, B. (2002). J. Invest. Dermatol. 118, 205-207.]); Kasraee et al. (2005[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.]) and for inhibiting tyrosinase, see: Liao et al. (2012[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.]). For typical bond lengths of intermolecular N-H...O=C hydrogen bonds, see: Taylor et al. (1984[Taylor, R., Kennard, O. & Versichel, W. (1984). Acta Cryst. B40, 280-288.]).

[Scheme 1]

Experimental

Crystal data
  • C13H21N3O4S

  • Mr = 315.39

  • Monoclinic, P 21 /c

  • a = 8.7636 (1) Å

  • b = 19.1184 (2) Å

  • c = 9.6735 (2) Å

  • [beta] = 98.485 (1)°

  • V = 1603.02 (4) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 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[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.550, Tmax = 1.000

  • 12262 measured reflections

  • 3093 independent reflections

  • 2923 reflections with I > 2[sigma](I)

  • Rint = 0.019

Refinement
  • R[F2 > 2[sigma](F2)] = 0.036

  • wR(F2) = 0.137

  • S = 1.05

  • 3093 reflections

  • 190 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.39 e Å-3

  • [Delta][rho]min = -0.53 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H3A...O1i 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[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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.  [CrossRef] [PubMed] [ChemPort]
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.  [CrossRef] [PubMed] [ChemPort]
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.  [ISI] [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Taylor, R., Kennard, O. & Versichel, W. (1984). Acta Cryst. B40, 280-288.  [CrossRef] [ISI] [details]


Acta Cryst (2012). E68, o3206  [ doi:10.1107/S1600536812043486 ]

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