Orphenadrinium dihydrogen citrate

Kaur, M.; Jasinski, J.P.; Keeley, A.C.; Yathirajan, H.S.; Siddaraju, B.P.

doi:10.1107/S1600536813001207

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 (C-C) = 0.004 Å
R = 0.056
wR = 0.161
Data-to-parameter ratio = 14.7
Details

Orphenadrinium dihydrogen citrate

Manpreet Kaur,^a Jerry P. Jasinski,^b ^* Amanda C. Keeley,^b H. S. Yathirajan ^a and B. P. Siddaraju ^c

^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-HO hydrogen bonds and weak O-HO 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). For related structures, see: Fun et al. (2010); Glaser et al. (1992); Jasinski et al. (2011). For standard bond lengths, see Allen et al. (1987).

Experimental

Crystal data

C₁₈H₂₄NO⁺·C₆H₇O₇^-
M_r = 461.50
Triclinic, $[P \overline 1]$
a = 9.9515 (8) Å
b = 10.7382 (9) Å
c = 12.625 (1) Å
= 98.863 (7)°
= 104.391 (7)°
= 111.498 (8)°
V = 1170.0 (2) Å³
Z = 2
Cu K radiation
= 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) T_min = 0.854, T_max = 1.000
7161 measured reflections
4471 independent reflections
3795 reflections with I > 2(I)
R_int = 0.029

Refinement

R[F² > 2(F²)] = 0.056
wR(F²) = 0.161
S = 1.03
4471 reflections
305 parameters
H-atom parameters constrained
_max = 0.67 e Å^-3
_min = -0.27 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O6ⁱ	0.91	1.83	2.725 (2)	167
O4-H4AO8ⁱⁱ	0.82	2.30	3.067 (2)	156
O7-H7AO5ⁱⁱ	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); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); 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.
Glaser, R., Donnel, D. & Maartmann-Moe, K. (1992). J. Pharm. Sci. 81, 858-862.
Hunskaar, S. & Donnel, D. (1991). J. Int. Med. Res. 19, 71-87.
Jasinski, J. P., Butcher, R. J., Siddaraju, B. P., Yathirajan, H. S. & Narayana, B. (2011). Acta Cryst. E67, o190-o191.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds

Orphenadrinium dihydrogen citrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Acknowledgements

References