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Volume 66 
Part 8 
Page o2150  
August 2010  

Received 20 July 2010
Accepted 26 July 2010
Online 31 July 2010

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.003 Å
R = 0.047
wR = 0.113
Data-to-parameter ratio = 18.7
Details
Open access

2-Amino-6-(2,6-difluorobenzamido)pyridinium chloride

aSchool of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia,bMalaysian Institute of Pharmaceuticals and Nutraceuticals, Ministry of Science, Technology and Innovation, Block A, 10 Persiaran Bukit Jambul, 11900 Bayan Lepas, Penang, Malaysia, and cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: hkfun@usm.my

In the cation of the title compound, C12H10F2N3O+·Cl-, the dihedral angle between the pyridine and benzene rings is 16.1 (1)°. In the crystal structure, molecules linked into two-dimensional sheets parallel to the bc plane by intermolecular N-H...Cl, C-H...Cl and C-H...F hydrogen bonds.

Related literature

For general background to 2,6-diflorobenzylchloride derivatives, see: Beavo (1995[Beavo, J. A. (1995). Physiol. Rev. 75, 725-748.]); Beavo & Reifsnyder (1990[Beavo, J. A. & Reifsnyder, D. H. (1990). Trends Pharmacol. Sci. 11, 150-155.]); Hidaka & Asano (1976[Hidaka, H. & Asano, T. (1976). Biochim. Biophys. Acta, 429, 485-497.]); Nicholson et al. (1991[Nicholson, C. D., Chaliss, R. A. & Shalid, M. (1991). Trends Pharmacol. Sci. 12, 19-27.]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • C12H10F2N3O+·Cl-

  • Mr = 285.68

  • Monoclinic, P 21 /c

  • a = 7.3196 (2) Å

  • b = 13.6314 (3) Å

  • c = 12.2892 (3) Å

  • [beta] = 99.755 (1)°

  • V = 1208.44 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.34 mm-1

  • T = 100 K

  • 0.34 × 0.12 × 0.08 mm

Data collection
  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.895, Tmax = 0.972

  • 11996 measured reflections

  • 3524 independent reflections

  • 2628 reflections with I > 2[sigma](I)

  • Rint = 0.041

Refinement
  • R[F2 > 2[sigma](F2)] = 0.047

  • wR(F2) = 0.113

  • S = 1.07

  • 3524 reflections

  • 188 parameters

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

  • [Delta][rho]max = 0.37 e Å-3

  • [Delta][rho]min = -0.35 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1N1...Cl1i 0.84 (3) 2.35 (2) 3.1622 (18) 163 (2)
N2-H1N2...Cl1 0.87 (2) 2.41 (2) 3.1678 (17) 146 (2)
N3-H1N3...Cl1ii 0.84 (2) 2.39 (2) 3.2140 (17) 166 (2)
N3-H2N3...Cl1 0.84 (2) 2.51 (2) 3.2346 (18) 145 (2)
C3-H3A...F2iii 0.93 2.52 3.414 (3) 162
C10-H10A...Cl1iv 0.93 2.74 3.581 (2) 151
Symmetry codes: (i) -x, -y+1, -z+1; (ii) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (iii) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (iv) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5090 ).


Acknowledgements

NM gratefully acknowledges funding from Universiti Sains Malaysia (USM) under the University Research Grant (No. 1001/PFARMASI/815025). HKF and CSY thank USM for the Research University Golden Goose Grant (No. 1001/PFIZIK/811012). CSY also thanks USM for the award of a USM Fellowship.

References

Beavo, J. A. (1995). Physiol. Rev. 75, 725-748.  [ChemPort] [PubMed] [ISI]
Beavo, J. A. & Reifsnyder, D. H. (1990). Trends Pharmacol. Sci. 11, 150-155.  [CrossRef] [ChemPort] [PubMed] [ISI]
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.  [CrossRef] [ChemPort] [ISI] [details]
Hidaka, H. & Asano, T. (1976). Biochim. Biophys. Acta, 429, 485-497.  [PubMed] [ISI]
Nicholson, C. D., Chaliss, R. A. & Shalid, M. (1991). Trends Pharmacol. Sci. 12, 19-27.  [CrossRef] [PubMed] [ChemPort] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2010). E66, o2150  [ doi:10.1107/S1600536810029624 ]

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