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Volume 69 
Part 4 
Page o512  
April 2013  

Received 16 February 2013
Accepted 26 February 2013
Online 9 March 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.006 Å
R = 0.070
wR = 0.200
Data-to-parameter ratio = 15.6
Details
Open access

[2-Acetoxy-3-(naphthalen-1-yloxy)propyl](propan-2-yl)azanium chloride monohydrate

aDepartment of Chemical and Pharmaceutical Engineering, Southeast University ChengXian College, Nanjing 210088, People's Republic of China
Correspondence e-mail: liuyuanyuan1985419@163.com

The title compound, C18H24NO3+·Cl-·H2O, was synthesized by the reaction of propranolol hydrochloride with acetyl chloride in chloroform followed by slow evaporation in air. In the cation, the dihedral angle between the planes of the naphthalene ring system and the acetate group is 71.1 (2)°. An intramolecular N-H...O hydrogen bond results in the formation of a non-planar pseudo-ring, with the ether O and the H atom displaced by -1.328 (2) and 0.65 Å, respectively, from the plane of the other ring atoms. The cation and anion are linked by an N-H...Cl hydrogen bond. The water molecule is linked to a methyl H atom by C-H...O hydrogen bond.

Related literature

The applications of the title compound, see: Barbosa et al. (2010[Barbosa, O., Ariza, C., Ortiz, C. & Torres, R. (2010). New Biotechnol. 27, 844-850.]). For the synthetic procedure, see: Irwin & Belaid (1987[Irwin, W. J. & Belaid, K. A. (1987). Drug Dev. Ind. Pharm. 13, 2017-2031.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C18H24NO3+·Cl-·H2O

  • Mr = 355.85

  • Monoclinic, P 21 /c

  • a = 15.559 (3) Å

  • b = 8.2120 (16) Å

  • c = 14.665 (3) Å

  • [beta] = 93.23 (3)°

  • V = 1870.8 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.23 mm-1

  • T = 293 K

  • 0.30 × 0.20 × 0.10 mm

Data collection
  • Enraf-Nonius CAD-4 diffractometer

  • Absorption correction: [psi] scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.936, Tmax = 0.978

  • 3424 measured reflections

  • 3424 independent reflections

  • 1948 reflections with I > 2[sigma](I)

  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.070

  • wR(F2) = 0.200

  • S = 0.99

  • 3424 reflections

  • 219 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.60 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N-H0A...Cl 0.90 2.37 3.194 (3) 152
N-H0A...O2 0.90 2.59 2.948 (3) 105
C15-H15B...O1Wi 0.96 2.53 3.469 (9) 166
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: CAD-4 Software (Enraf-Nonius, 1985[Enraf-Nonius (1985). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); 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: BQ2383 ).


Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for the data collection.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Barbosa, O., Ariza, C., Ortiz, C. & Torres, R. (2010). New Biotechnol. 27, 844-850.  [CrossRef] [ChemPort]
Enraf-Nonius (1985). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Irwin, W. J. & Belaid, K. A. (1987). Drug Dev. Ind. Pharm. 13, 2017-2031.  [CrossRef] [ChemPort] [ISI]
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2013). E69, o512  [ doi:10.1107/S1600536813005515 ]

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