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

Al-Dajani, M.T.M.; Mohamed, N.; Wahab, H.A.; Yeap, C.S.; Fun, H.-K.

doi:10.1107/S1600536810029624

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 (C-C) = 0.003 Å
R = 0.047
wR = 0.113
Data-to-parameter ratio = 18.7
Details

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

Mohammad T. M. Al-Dajani,^a Nornisah Mohamed,^a Habibah A. Wahab,^b Chin Sing Yeap ^c ⁺ and Hoong-Kun Fun ^c ^*⁺⁺

^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-HCl, C-HCl and C-HF hydrogen bonds.

Related literature

For general background to 2,6-diflorobenzylchloride derivatives, see: Beavo (1995); Beavo & Reifsnyder (1990); Hidaka & Asano (1976); Nicholson et al. (1991). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental

Crystal data

C₁₂H₁₀F₂N₃O⁺·Cl^-
M_r = 285.68
Monoclinic, P 2₁ /c
a = 7.3196 (2) Å
b = 13.6314 (3) Å
c = 12.2892 (3) Å
= 99.755 (1)°
V = 1208.44 (5) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.895, T_max = 0.972
11996 measured reflections
3524 independent reflections
2628 reflections with I > 2(I)
R_int = 0.041

Refinement

R[F² > 2(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
_max = 0.37 e Å^-3
_min = -0.35 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1N1Cl1ⁱ	0.84 (3)	2.35 (2)	3.1622 (18)	163 (2)
N2-H1N2Cl1	0.87 (2)	2.41 (2)	3.1678 (17)	146 (2)
N3-H1N3Cl1ⁱⁱ	0.84 (2)	2.39 (2)	3.2140 (17)	166 (2)
N3-H2N3Cl1	0.84 (2)	2.51 (2)	3.2346 (18)	145 (2)
C3-H3AF2ⁱⁱⁱ	0.93	2.52	3.414 (3)	162
C10-H10ACl1^iv	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); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).

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

organic compounds