[Journal logo]

Volume 65 
Part 2 
Page o303  
February 2009  

Received 20 November 2008
Accepted 7 January 2009
Online 14 January 2009

[gw2057sup1]
[3d view]

[Cited in]
[Download citation]
Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.004 Å
Disorder in solvent or counterion
R = 0.081
wR = 0.218
Data-to-parameter ratio = 12.8
Details
Open access

Norfloxacin sesquihydrate

Nittala V. Ravindra,a Gopal M. Panpaliaa and A. R. P. Sarma Jagarlapudib*

aBirla Institute of Technology, Department of Pharmaceutical Sciences, Mesra, Ranchi 835 215, India, and bGVK Biosciences Private Limited, S-1, Phase-1 Technocrats Industrial Estate, Balanagar, Hyderabad 500 037, India
Correspondence e-mail: sarma@gvkbio.com

In the crystal structure of the title compound [systematic name: 1-ethyl-6-fluoro-4-oxo-7-(piperazin-4-ium-1-yl)-1,4-dihydroquinoline-3-carboxylate sesquihydrate], C16H18FN3O3·1.42H2O, N-H...O and O-H...O hydrogen bonds assemble the molecules in a two-dimensional layered corrugated sheet structure parallel to the b axis. The water molecules are disordered [occupancies 0.741 (11) and 0.259 (11)].

Related literature

For related structures, see: Yuasa et al. (1982[Yuasa, R., Imai, J., Morikawa, H., Kusajima, H., Uchida, H. & Irikura, T. (1982). Yakugaku Zasshi, 102, 469-476.]); Windholz et al. (1983[Windholz, M., Budavari, S., Blumetti, R. F. & Otterbein, E. S. (1983). Editors. The Merck Index, 10th ed. Rahway, NJ, USA: Merck and Co. Inc.]); Katdare et al. (1986[Katdare, A. V., Ryan, J. A., Bavitz, J. F., Erb, D. M. & Guillory, J. K. (1986). Mikrochim. Acta Wien III, 90, 1-12.]); Sustar et al. (1993[Sustar, B., Bukovec, N. & Bukovec, P. (1993). J. Therm. Anal. 40, 475-481.]); Florence et al. (2000[Florence, A. J., Kennedy, A. R., Shankland, N., Wright, E. & Al-Rubayi, A. (2000). Acta Cryst. C56, 1372-1373.]); Barbas et al. (2006[Barbas, R., Martí, F., Prohens, R. & Puigjaner, C. (2006). Cryst. Growth Des. 6, 1463-1467.]); Basavoju et al. (2006[Basavoju, S., Boström, D. & Velaga, S. P. (2006). Cryst. Growth Des. 6, 2699-2708.]); Barbas et al. (2007[Barbas, R., Prohens, R. & Puigjaner, C. (2007). J. Therm. Anal. Calorim. 89, 687-692.]); Chongcharoen et al. (2008[Chongcharoen, W., Byrn, S. R. & Sutanthavibul, N. (2008). J. Pharm. Sci. 97, 473-489.])

[Scheme 1]

Experimental

Crystal data

  • C16H18FN3O3·1.42H2O

  • Mr = 344.12

  • Monoclinic, P 21 /c

  • a = 8.8434 (18) Å

  • b = 22.312 (5) Å

  • c = 8.7564 (18) Å

  • [beta] = 109.35 (3)°

  • V = 1630.2 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 298 (2) K

  • 0.20 × 0.20 × 0.10 mm
Data collection

  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: none

  • 16819 measured reflections

  • 3228 independent reflections

  • 2553 reflections with I > 2[sigma](I)

  • Rint = 0.044
Refinement

  • R[F2 > 2[sigma](F2)] = 0.081

  • wR(F2) = 0.218

  • S = 1.03

  • 3228 reflections

  • 253 parameters

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

  • [Delta][rho]max = 0.37 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H3A...O4A 0.90 1.88 (1) 2.741 160
N3-H3A...O4B 0.90 2.10 (1) 2.952 157
N3-H3B...O2i 0.90 1.99 2.777 (4) 145
N3-H3B...O3i 0.90 2.15 2.793 (4) 128
O4B-H4B...O1ii 0.912 (7) 2.02 (7) 2.793 141
O4A-H4A...O2iii 0.933 (10) 1.90 (9) 2.811 165
Symmetry codes: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iii) [x-1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}].

Data collection: SMART (Bruker, 1997[Bruker (1997). SMART and SAINT. Bruker AXS Inc.,Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1997[Bruker (1997). SMART 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GW2057 ).

Acknowledgements

NVR thanks the Birla Institute of Technology for financial support. NVR also thanks Jagadeesh Babu and Professor Ashwini Nangia, University of Hyderabad, for help in X-ray diffraction.

References

Barbas, R., Martí, F., Prohens, R. & Puigjaner, C. (2006). Cryst. Growth Des. 6, 1463-1467.  [CrossRef] [ChemPort]
Barbas, R., Prohens, R. & Puigjaner, C. (2007). J. Therm. Anal. Calorim. 89, 687-692.  [ISI] [CSD] [CrossRef] [ChemPort]
Basavoju, S., Boström, D. & Velaga, S. P. (2006). Cryst. Growth Des. 6, 2699-2708.  [CSD] [CrossRef] [ChemPort]
Bruker (1997). SMART and SAINT. Bruker AXS Inc.,Madison, Wisconsin, USA.
Chongcharoen, W., Byrn, S. R. & Sutanthavibul, N. (2008). J. Pharm. Sci. 97, 473-489.  [ISI] [CrossRef] [PubMed] [ChemPort]
Florence, A. J., Kennedy, A. R., Shankland, N., Wright, E. & Al-Rubayi, A. (2000). Acta Cryst. C56, 1372-1373.  [CrossRef] [details]
Katdare, A. V., Ryan, J. A., Bavitz, J. F., Erb, D. M. & Guillory, J. K. (1986). Mikrochim. Acta Wien III, 90, 1-12.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Sustar, B., Bukovec, N. & Bukovec, P. (1993). J. Therm. Anal. 40, 475-481.
Windholz, M., Budavari, S., Blumetti, R. F. & Otterbein, E. S. (1983). Editors. The Merck Index, 10th ed. Rahway, NJ, USA: Merck and Co. Inc.
Yuasa, R., Imai, J., Morikawa, H., Kusajima, H., Uchida, H. & Irikura, T. (1982). Yakugaku Zasshi, 102, 469-476.  [ChemPort] [PubMed] [ISI]

Acta Cryst (2009). E65, o303  [ doi:10.1107/S160053680900066X ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.