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Volume 67 
Part 6 
Page m786  
June 2011  

Received 21 March 2011
Accepted 17 May 2011
Online 25 May 2011

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Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.003 Å
Disorder in main residue
R = 0.054
wR = 0.149
Data-to-parameter ratio = 16.3
Details
Open access

Poly[([mu]3-rac-5-ethoxycarbonyl-6-hydroxy-6-methyl-4-phenyl-4,5,6,7-tetrahydrobenzo[c]isoxazol-3-olato)potassium]

Abel M. Maharramov,a* Arif I. Ismiyeva and Bahruz A. Rashidova

aBaku State University, Z. Khalilov St. 23, Baku AZ-1148, Azerbaijan
Correspondence e-mail: orglab@mail.ru

The title compound, [K(C17H18NO5)]n, reveals the relative configuration (4R*,5S*,6R*) whereas its crystals are racemic. The cyclohexane ring adopts a half-chair conformation and the isoxazole ring has an envelope conformation. The ethyl fragment of the ethoxycarbonyl group at position 5 is disordered in a 0.547 (7):0.453 (7) ratio. The K+ ion is surrounded by five O atoms from three ligands at distances ranging from 2.606 (2) to 3.028 (2) Å, generating a three-dimensional network. The crystal packing displays intermolecular O-H...N and O-H...O hydrogen bonds in which the hydroxy group acts as a double proton donor.

Related literature

For background to the microbiological activity of 2-azetidinone derivatives, see: Wadher et al. (2009[Wadher, S. J., Puranik, M. P., Karande, N. A. & Yeole, P. G. (2009). Int. J. PharmTech Res. 1, 22-33.]).

[Scheme 1]

Experimental

Crystal data

  • [K(C17H18NO5)]

  • Mr = 355.42

  • Monoclinic, P 21 /c

  • a = 12.4811 (18) Å

  • b = 15.411 (2) Å

  • c = 8.6647 (12) Å

  • [beta] = 94.388 (5)°

  • V = 1661.7 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.35 mm-1

  • T = 100 K

  • 0.30 × 0.30 × 0.20 mm
Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1998[Sheldrick, G. M. (1998). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.903, Tmax = 0.934

  • 16716 measured reflections

  • 3594 independent reflections

  • 2977 reflections with I > 2[sigma](I)

  • Rint = 0.042
Refinement

  • R[F2 > 2[sigma](F2)] = 0.054

  • wR(F2) = 0.149

  • S = 0.99

  • 3594 reflections

  • 221 parameters

  • 6 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.68 e Å-3

  • [Delta][rho]min = -0.64 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O6-H6O...N1i 0.91 1.88 2.784 (3) 177
O6-H6O...O2i 0.91 2.55 3.336 (3) 145
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, 2001[Bruker (2001). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KP2318 ).

Acknowledgements

We thank Professor Victor N. Khrustalev for fruitful discussions and help with this work.

References

Bruker (2001). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (1998). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Wadher, S. J., Puranik, M. P., Karande, N. A. & Yeole, P. G. (2009). Int. J. PharmTech Res. 1, 22-33.  [ChemPort]

Acta Cryst (2011). E67, m786  [ doi:10.1107/S160053681101868X ]

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