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Volume 69 
Part 2 
Page o248  
February 2013  

Received 11 January 2013
Accepted 12 January 2013
Online 19 January 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.004 Å
R = 0.056
wR = 0.161
Data-to-parameter ratio = 14.7
Details
Open access

Orphenadrinium dihydrogen citrate

aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India,bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, and cDepartment of Chemistry, G. Madegowda Institute of Technology, Bharathinagara 571 442, India
Correspondence e-mail: jjasinski@keene.edu

In the title salt, C18H24NO+·C6H7O7-, the dihedral angle between the benzene rings in the cation is 74.2 (5)°. In the crystal, anion-anion O-H...O hydrogen bonds and weak O-H...O interactions form infinite chains along [100]. Between these chains, cation-anion N-H-O hydrogen bonds are observed, forming an alternate pattern of cation and anion layers and leading to a two-dimensional network parallel to (100).

Related literature

For a clinical and pharmacological review of the efficacy of orphenadrine, see: Hunskaar & Donnel (1991[Hunskaar, S. & Donnel, D. (1991). J. Int. Med. Res. 19, 71-87.]). For related structures, see: Fun et al. (2010[Fun, H.-K., Hemamalini, M., Siddaraju, B. P., Yathirajan, H. S. & Narayana, B. (2010). Acta Cryst. E66, o682-o683.]); Glaser et al. (1992[Glaser, R., Donnel, D. & Maartmann-Moe, K. (1992). J. Pharm. Sci. 81, 858-862.]); Jasinski et al. (2011[Jasinski, J. P., Butcher, R. J., Siddaraju, B. P., Yathirajan, H. S. & Narayana, B. (2011). Acta Cryst. E67, o190-o191.]). For standard bond lengths, 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
  • C18H24NO+·C6H7O7-

  • Mr = 461.50

  • Triclinic, [P \overline 1]

  • a = 9.9515 (8) Å

  • b = 10.7382 (9) Å

  • c = 12.625 (1) Å

  • [alpha] = 98.863 (7)°

  • [beta] = 104.391 (7)°

  • [gamma] = 111.498 (8)°

  • V = 1170.0 (2) Å3

  • Z = 2

  • Cu K[alpha] radiation

  • [mu] = 0.82 mm-1

  • T = 173 K

  • 0.32 × 0.28 × 0.14 mm

Data collection
  • Agilent Xcalibur (Eos, Gemini) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]) Tmin = 0.854, Tmax = 1.000

  • 7161 measured reflections

  • 4471 independent reflections

  • 3795 reflections with I > 2[sigma](I)

  • Rint = 0.029

Refinement
  • R[F2 > 2[sigma](F2)] = 0.056

  • wR(F2) = 0.161

  • S = 1.03

  • 4471 reflections

  • 305 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.67 e Å-3

  • [Delta][rho]min = -0.27 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O6i 0.91 1.83 2.725 (2) 167
O4-H4A...O8ii 0.82 2.30 3.067 (2) 156
O7-H7A...O5ii 0.82 1.81 2.634 (2) 178
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x+1, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); 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: HG5283 ).


Acknowledgements

MK and HSY thank the University of Mysore for research facilities. JPJ acknowledges the NSF-MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

References

Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.
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.
Fun, H.-K., Hemamalini, M., Siddaraju, B. P., Yathirajan, H. S. & Narayana, B. (2010). Acta Cryst. E66, o682-o683.  [CSD] [CrossRef] [details]
Glaser, R., Donnel, D. & Maartmann-Moe, K. (1992). J. Pharm. Sci. 81, 858-862.  [CrossRef] [PubMed] [ChemPort] [ISI]
Hunskaar, S. & Donnel, D. (1991). J. Int. Med. Res. 19, 71-87.  [PubMed] [ChemPort]
Jasinski, J. P., Butcher, R. J., Siddaraju, B. P., Yathirajan, H. S. & Narayana, B. (2011). Acta Cryst. E67, o190-o191.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2013). E69, o248  [ doi:10.1107/S1600536813001207 ]

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