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Volume 69 
Part 12 
Page o1779  
December 2013  

Received 7 November 2013
Accepted 11 November 2013
Online 16 November 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.002 Å
R = 0.038
wR = 0.109
Data-to-parameter ratio = 17.3
Details
Open access

Methyl 2-amino-4,5-di­meth­oxy­benzoate

aMolecular Sciences Institute, School of Chemistry, University of the Witwatersrand, PO WITS 2050, Johannesburg, South Africa
Correspondence e-mail: tania.hill@gmail.com

The title compound, C10H13NO4, is essentially planar, with an r.m.s. deviation of 0.049 Å. An intra­molecular C-H...O hydrogen bond occurs and the amino group forms an intra­molecular N-H...Oester hydrogen bond; the other H atom forms an inter­molecular N-H...Ocarbon­yl hydrogen bond, leading to the formation of a helical chain that runs along the b-axis direction.

Related literature

For similar crystal structures, see: Zhang et al. (2009[Zhang, M., Lu, R., Han, L., Wei, W. & Wang, H. (2009). Acta Cryst. E65, o942.]); Smith & Elsegood (2002[Smith, M. B. & Elsegood, M. R. J. (2002). Tetrahedron Lett. 43, 1299-1301.]).

[Scheme 1]

Experimental

Crystal data
  • C10H13NO4

  • Mr = 211.21

  • Monoclinic, P 21 /c

  • a = 11.1933 (4) Å

  • b = 7.7564 (3) Å

  • c = 13.7728 (5) Å

  • [beta] = 121.741 (2)°

  • V = 1016.91 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 173 K

  • 0.5 × 0.29 × 0.25 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). SAINT-Plus, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin. USA.]) Tmin = 0.948, Tmax = 0.974

  • 9994 measured reflections

  • 2543 independent reflections

  • 2080 reflections with I > 2[sigma](I)

  • Rint = 0.035

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.109

  • S = 1.05

  • 2543 reflections

  • 147 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.27 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C6-H6...O2 0.95 2.37 2.7131 (14) 101
N1-H1A...O1 0.90 (2) 2.03 (2) 2.702 (2) 131 (2)
N1-H1B...O1i 0.88 (2) 2.10 (2) 2.947 (1) 162 (1)
Symmetry code: (i) [-x, y+{\script{1\over 2}}, -z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2004[Bruker (2004). SAINT-Plus, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin. USA.]); data reduction: SAINT-Plus and XPREP (Bruker, 2004[Bruker (2004). SAINT-Plus, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin. USA.]); 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: DIAMOND (Brandenburg & Putz, 2005[Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Imapct GbR, Bonn, Germany.]); software used to prepare material for publication: WinGX (Farrugia, 2012)[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.].


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG5347 ).


Acknowledgements

The University of the Witwatersrand and the Mol­ecular Sciences Institute are thanked for providing the infrastructure and financial support. Special thanks go to Dr Andreas Lemmerer of the University of the Witwatersrand for his contributions and insights toward this project. TNH wishes to thank the University of the Witwatersrand research committee for a postdoctoral fellowship.

References

Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Imapct GbR, Bonn, Germany.
Bruker (2004). SAINT-Plus, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin. USA.
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Smith, M. B. & Elsegood, M. R. J. (2002). Tetrahedron Lett. 43, 1299-1301.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Zhang, M., Lu, R., Han, L., Wei, W. & Wang, H. (2009). Acta Cryst. E65, o942.  [CSD] [CrossRef] [IUCr Journals]


Acta Cryst (2013). E69, o1779  [ doi:10.1107/S1600536813030894 ]

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