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Volume 67 
Part 10 
Pages o2773-o2774  
October 2011  

Received 5 September 2011
Accepted 13 September 2011
Online 30 September 2011

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Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.005 Å
R = 0.039
wR = 0.118
Data-to-parameter ratio = 14.3
Details
Open access

Moxifloxacinium chloride monohydrate

Jing-Jing Qian,a Jian-Ming Gu,b Jin Shen,a Xiu-Rong Huc* and Su-Xiang Wua

aCollege of Pharmaceutical Science, Zhejiang Chinese Medical University, Hangzhou, Zhejiang 310053, People's Republic of China,bCenter of Analysis and Measurement, Zhejiang University, Hangzhou, Zhejiang 310028, People's Republic of China, and cChemistry Department, Zhejiang University, Hangzhou, Zhejiang 310028, People's Republic of China
Correspondence e-mail: huxiurong@yahoo.com.cn

The title compound {systematic name: 7-[(1S,6S)-8-aza-2-azoniabicyclo[4.3.0]non-8-yl]-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid chloride monohydrate}, C21H25FN3O4+·Cl-·H2O, crystallizes with two moxifloxacinium cations, two chloride ions and two uncoordinated water molecules in the unit cell. The crystal structure has a pseudo-inversion center except for the chloride ions. In both moxifloxacinium cations, the quinoline rings are approximately planar, the maximum atomic deviations being 0.107 (3) and 0.118 (3) Å. The piperidine rings adopt a chair conformation while the pyrrolidine rings display a half-chair conformation. In the crystal, the carboxyl groups, the protonated piperidyl groups, the uncoordinated water molecule and chloride anions participate in O-H...O, O-H...Cl and N-H...Cl hydrogen bonding; weak intermolecular C-H...O and C-H...Cl hydrogen bonding is also present in the crystal structure.

Related literature

For applications of moxifloxacin hydrochloride in the medicine field, see: Seidel et al. (2000[Seidel, D., Conrad, M., Brehmer, P., Mohrs, K. & Petersen, U. (2000). J. Labelled Compd Radiopharm. 43, 795-805.]); Talib et al. (2002[Talib, S. H., Arshad, M., Chauhan, H., Jain, R. & Vaya, L. (2002). J. Indian Acad. Clin. Med. 3, 360-366.]); Culley et al. (2001[Culley, C. M., Lacy, M. K., Klutman, N. & Edwards, B. (2001). Am. J. Health Syst. Pharm. 58, 379-388.]); Liu & Sun (2008[Liu, H. & Sun, F. G. (2008). Adverse Drug React. J. 10, 141-142.]). For the tolerability, solubility, safety and pharmacodynamics of moxifloxacin hydrochloride, see: Stass et al. (1998[Stass, H., Dalhoff, A., Kubitza, D. & Schuhly, U. (1998). Antimicrob. Agents Chemother. 42, 2060-2065.]); Noel et al. (2005[Noel, A. R., Bowker, K. E. & MacGowan, A. P. (2005). Antimicrob. Agents Chemother. 49, 4234-4239.]); Varanda et al. (2006[Varanda, F., Pratas de Melo, M. J., Cac\,o, A. I., Dohrn, R., Makrydaki, F. A., Voutsas, E., Tassios, D. & Marrucho, I. M. (2006). Ind. Eng. Chem. Res. 45, 6368-6374.]). For a related structure of moxifloxacin hydrochloride methanol solvate, see: Ravikumar & Sridhar (2006[Ravikumar, K. & Sridhar, B. (2006). Acta Cryst. C62, o478-o482.]).

[Scheme 1]

Experimental

Crystal data

  • C21H25FN3O4+·Cl-·H2O

  • Mr = 455.91

  • Triclinic, P 1

  • a = 6.7280 (3) Å

  • b = 10.6406 (5) Å

  • c = 15.3127 (7) Å

  • [alpha] = 91.7293 (14)°

  • [beta] = 91.1313 (13)°

  • [gamma] = 100.8823 (13)°

  • V = 1075.67 (9) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.23 mm-1

  • T = 296 K

  • 0.49 × 0.37 × 0.22 mm
Data collection

  • Rigaku R-AXIS RAPID/ZJUG diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.898, Tmax = 0.952

  • 10677 measured reflections

  • 8038 independent reflections

  • 5933 reflections with I > 2[sigma](I)

  • Rint = 0.024
Refinement

  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.118

  • S = 1.10

  • 8038 reflections

  • 563 parameters

  • 3 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.25 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 3107 Friedel pairs

  • Flack parameter: 0.00 (6)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1A-H12A...Cl1Bi 0.90 2.26 3.113 (3) 158
N1A-H13A...Cl1A 0.90 2.43 3.234 (3) 150
N1B-H12B...Cl1Aii 0.90 2.22 3.109 (3) 170
N1B-H13B...Cl1B 0.90 2.25 3.114 (2) 162
O3A-H3A...O2A 0.82 1.74 2.512 (4) 156
O3B-H3B...O2B 0.82 1.74 2.508 (4) 155
O5A-H51A...O4A 0.82 2.24 3.011 (5) 157
O5A-H52A...Cl1B 0.82 2.72 3.422 (5) 144
O5B-H51B...O4B 0.82 2.12 2.911 (5) 161
O5B-H52B...Cl1Biii 0.82 2.41 3.208 (4) 163
C1A-H1A...O3B 0.98 2.53 3.373 (4) 144
C2A-H21A...Cl1Aiv 0.97 2.80 3.742 (4) 163
C3A-H31A...Cl1A 0.97 2.74 3.518 (5) 138
C3A-H32A...O1Bv 0.97 2.59 3.450 (5) 148
C6A-H61A...O3Bvi 0.97 2.49 3.340 (6) 146
C18B-H18B...O5Avii 0.98 2.58 3.564 (7) 179
Symmetry codes: (i) x, y+1, z+1; (ii) x, y, z-1; (iii) x+1, y+1, z+1; (iv) x+1, y, z; (v) x, y, z+1; (vi) x-1, y, z; (vii) x+1, y+1, z.

Data collection: PROCESS-AUTO (Rigaku, 2006[Rigaku (2006). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku, 2007[Rigaku (2007). CrystalStructure. Rigaku, Tokyo, Japan.]); 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, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5322 ).

Acknowledgements

The project was supported by the Zhejiang Provincial Natural Science Foundation of China (J200801).

References

Culley, C. M., Lacy, M. K., Klutman, N. & Edwards, B. (2001). Am. J. Health Syst. Pharm. 58, 379-388.  [ChemPort]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Liu, H. & Sun, F. G. (2008). Adverse Drug React. J. 10, 141-142.
Noel, A. R., Bowker, K. E. & MacGowan, A. P. (2005). Antimicrob. Agents Chemother. 49, 4234-4239.  [ISI] [CrossRef] [ChemPort]
Ravikumar, K. & Sridhar, B. (2006). Acta Cryst. C62, o478-o482.  [CSD] [CrossRef] [details]
Rigaku (2006). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.
Rigaku (2007). CrystalStructure. Rigaku, Tokyo, Japan.
Seidel, D., Conrad, M., Brehmer, P., Mohrs, K. & Petersen, U. (2000). J. Labelled Compd Radiopharm. 43, 795-805.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Stass, H., Dalhoff, A., Kubitza, D. & Schuhly, U. (1998). Antimicrob. Agents Chemother. 42, 2060-2065.  [ChemPort]
Talib, S. H., Arshad, M., Chauhan, H., Jain, R. & Vaya, L. (2002). J. Indian Acad. Clin. Med. 3, 360-366.
Varanda, F., Pratas de Melo, M. J., Cac\,o, A. I., Dohrn, R., Makrydaki, F. A., Voutsas, E., Tassios, D. & Marrucho, I. M. (2006). Ind. Eng. Chem. Res. 45, 6368-6374.

Acta Cryst (2011). E67, o2773-o2774   [ doi:10.1107/S160053681103707X ]

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