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Volume 69 
Part 8 
Pages o1264-o1265  
August 2013  

Received 4 July 2013
Accepted 8 July 2013
Online 17 July 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.003 Å
R = 0.050
wR = 0.145
Data-to-parameter ratio = 12.8
Details
Open access

Carbinoxaminium dipicrate

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 cSri Mahadeshwara Government First Grade College, Affiliated to University of Mysore, Kollegal 571 440, India
Correspondence e-mail: jjasinski@keene.edu

In the dication of the title salt, C16H21ClN2O2+·2C6H2N3O7- [systematic name: 2-{(4-chlorophenyl)[2-(dimethylazaniumyl)ethoxy]methyl}pyridinium bis(2,4,6-trinitrophenolate), contains a carbinoxaminium dication and two picrate anions, which are held together through intermolecular N-H...O hydrogen bonds. In the dication, the two aromatic rings form a dihedral angle of 80.1 (1)°. In the two independent picrate anions, the nitro groups are twisted from the benzene plane, the largest dihedral angle in each ion being 42.8 (1) and 81.1 (5)°. In the crystal, in addition to the classical N-H...O hydrogen bonds, weak C-H...O hydrogen bonds and [pi]-[pi] interactions between the aromatic rings of the anions [centroid-centroid distances of 3.5768 (15) and 3.7436 (15) Å] help to establish the packing.

Related literature

For the pharmacological importance of antihistamines, see: Wagner (1962[Wagner, H. J. (1962). Arzneim.-Forsch. 12, 1065-1070.]). For the effect of antihistamines on psychomotor performance, see: Seppala et al. (1981[Seppala, T., Nuotto, E. & Korttila, K. (1981). Br. J. Clin. Pharmacol. 12, 179-188.]). For related structures, see: Bertolasi et al. (1980[Bertolasi, V., Borea, P. A., Gilli, G. & Sacerdoti, M. (1980). Acta Cryst. B36, 2287-2291.]); Parvez et al. (2001[Parvez, M., Dalrymple, S. & Cote, A. (2001). Acta Cryst. E57, o163-o165.]); Fun et al. (2010[Fun, H.-K., Hemamalini, M., Siddaraju, B. P., Yathirajan, H. S. & Narayana, B. (2010). Acta Cryst. E66, o682-o683.]); Kaur et al. (2013[Kaur, M., Jasinski, J. P., Keeley, A. C., Yathirajan, H. S. & Siddaraju, B. P. (2013). Acta Cryst. E69, o248.]). 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
  • C16H21ClN2O2+·2C6H2N3O7-

  • Mr = 749.01

  • Triclinic, [P \overline 1]

  • a = 8.1719 (6) Å

  • b = 8.5341 (6) Å

  • c = 23.5868 (16) Å

  • [alpha] = 83.771 (6)°

  • [beta] = 85.484 (6)°

  • [gamma] = 74.827 (6)°

  • V = 1576.1 (2) Å3

  • Z = 2

  • Cu K[alpha] radiation

  • [mu] = 1.87 mm-1

  • T = 173 K

  • 0.24 × 0.16 × 0.12 mm

Data collection
  • Agilent Xcalibur (Eos, Gemini) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.871, Tmax = 1.000

  • 9838 measured reflections

  • 6071 independent reflections

  • 4958 reflections with I > 2[sigma](I)

  • Rint = 0.036

Refinement
  • R[F2 > 2[sigma](F2)] = 0.050

  • wR(F2) = 0.145

  • S = 1.02

  • 6071 reflections

  • 476 parameters

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

  • [Delta][rho]max = 0.42 e Å-3

  • [Delta][rho]min = -0.38 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O1B 0.83 (3) 1.81 (3) 2.628 (2) 167 (3)
N2-H2...O1A 1.00 1.78 2.737 (3) 159
C1-H1A...O1B 1.00 2.43 3.183 (2) 132
C3-H3...O7A 0.95 2.53 3.366 (3) 148
C9-H9...O2Bi 0.95 2.38 3.137 (3) 136
C9-H9...O7B 0.95 2.36 2.956 (3) 120
C11-H11...O5Aii 0.95 2.49 3.309 (3) 144
C12-H12...O1A 0.95 2.59 3.430 (3) 148
C14-H14B...O5Aiii 0.99 2.46 3.253 (3) 137
C15-H15B...O4Aiv 0.98 2.59 3.400 (3) 140
C16-H16A...O5Bv 0.98 2.58 3.483 (3) 154
Symmetry codes: (i) x, y-1, z; (ii) -x+1, -y+1, -z+1; (iii) -x+1, -y+2, -z+1; (iv) -x+2, -y+1, -z+1; (v) -x+2, -y+2, -z.

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007[Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.]); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: OLEX2.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV5423 ).


Acknowledgements

VR thanks the UOM for research facilities to complete the MSc dissertation work. JPJ acknowledges the NSF-MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

References

Agilent (2012). CrysAlis PRO. 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.
Bertolasi, V., Borea, P. A., Gilli, G. & Sacerdoti, M. (1980). Acta Cryst. B36, 2287-2291.  [CrossRef] [IUCr Journals]
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Fun, H.-K., Hemamalini, M., Siddaraju, B. P., Yathirajan, H. S. & Narayana, B. (2010). Acta Cryst. E66, o682-o683.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Kaur, M., Jasinski, J. P., Keeley, A. C., Yathirajan, H. S. & Siddaraju, B. P. (2013). Acta Cryst. E69, o248.  [CSD] [CrossRef] [IUCr Journals]
Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Parvez, M., Dalrymple, S. & Cote, A. (2001). Acta Cryst. E57, o163-o165.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Seppala, T., Nuotto, E. & Korttila, K. (1981). Br. J. Clin. Pharmacol. 12, 179-188.  [ChemPort] [PubMed] [Web of Science]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Wagner, H. J. (1962). Arzneim.-Forsch. 12, 1065-1070.  [ChemPort]


Acta Cryst (2013). E69, o1264-o1265   [ doi:10.1107/S1600536813018886 ]

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