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Volume 69 
Part 9 
Page o1404  
September 2013  

Received 31 July 2013
Accepted 4 August 2013
Online 10 August 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.040
wR = 0.107
Data-to-parameter ratio = 13.6
Details
Open access

2-(3,5-Dioxo-4-azatricyclo[5.2.1.02,6]dec-8-en-4-yl)acetic acid

aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey,bDepartment of Chemistry, College of Sciences, Shiraz University, 71454 Shiraz, Iran, and cDepartment of Physics, University of Sargodha, Sargodha, Pakistan
Correspondence e-mail: dmntahir_uos@yahoo.com

The asymmetric unit of the title compound, C11H11NO4, contains two molecules, A and B, with different conformations: in molecule A, the norborne and carboxylic acid groups lie to the same side of the heterocycle, whereas in a molecule B, they lie on opposite sides. In the crystal, the A molecules form R22(8) carboxylic acid inversion dimers, linked by pairs of O-H...O hydrogen bonds. The B molecules link to one of the ketone O atoms of the A molecule by an O-H...O interaction, resulting in tetramers (two A and two B molecules). The tetramers are linked by weak C-H...O interactions, generating a three-dimensional network.

Related literature

For a related structure, see: Bartkowska et al. (1997[Bartkowska, B., Bohnen, F. M., Krüger, C. & Maier, W. F. (1997). Acta Cryst. C53, 521-522.]). For further synthetic details, see: Biagini et al. (1995[Biagini, S. C. G., Bush, S. M., Gibson, V. C., Mazzariol, L., North, M., Teasdale, W. G., Williams, C. M., Zagotto, G. & Zamuner, D. (1995). Tetrahedron, 51, 7247-7262.]).

[Scheme 1]

Experimental

Crystal data
  • C11H11NO4

  • Mr = 221.21

  • Triclinic, [P \overline 1]

  • a = 6.5060 (3) Å

  • b = 11.8417 (4) Å

  • c = 14.1794 (5) Å

  • [alpha] = 104.385 (2)°

  • [beta] = 97.905 (2)°

  • [gamma] = 99.549 (2)°

  • V = 1025.07 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 296 K

  • 0.28 × 0.20 × 0.16 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.970, Tmax = 0.983

  • 15543 measured reflections

  • 3985 independent reflections

  • 3245 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.107

  • S = 1.03

  • 3985 reflections

  • 292 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...O2i 0.82 1.84 2.6504 (18) 170
O5-H5A...O3ii 0.82 1.86 2.6509 (18) 163
C11-H11...O8iii 0.93 2.57 3.440 (2) 156
C15-H15...O8iv 0.98 2.33 3.201 (2) 147
C16-H16...O1iv 0.98 2.48 3.1473 (19) 125
Symmetry codes: (i) -x-1, -y+1, -z+1; (ii) -x, -y+2, -z+1; (iii) -x, -y+1, -z+1; (iv) x+1, y, z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7113 ).


Acknowledgements

The authors acknowledge the provision of funds for the purchase of a diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan. AJ and PS thanks Shiraz University Research Council for financial support (grant No. 91-GR-SC-23).

References

Bartkowska, B., Bohnen, F. M., Krüger, C. & Maier, W. F. (1997). Acta Cryst. C53, 521-522.  [CSD] [CrossRef] [details]
Biagini, S. C. G., Bush, S. M., Gibson, V. C., Mazzariol, L., North, M., Teasdale, W. G., Williams, C. M., Zagotto, G. & Zamuner, D. (1995). Tetrahedron, 51, 7247-7262.  [CrossRef] [ChemPort] [ISI]
Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o1404  [ doi:10.1107/S1600536813021764 ]

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