4-Carboxy­pyridazin-1-ium chloride

Starosta, W.; Leciejewicz, J.

doi:10.1107/S1600536808022319

Volume 64
Part 8
Page o1553
August 2008

Received 4 July 2008
Accepted 16 July 2008
Online 19 July 2008

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R = 0.030
wR = 0.105
Data-to-parameter ratio = 19.4
Details

4-Carboxypyridazin-1-ium chloride

Wojciech Starosta ^a and Janusz Leciejewicz ^a ^*

^aInstitute of Nuclear Chemistry and Technology, ulica Dorodna 16, 03-195 Warszawa, Poland
Correspondence e-mail: jlec@ichtj.waw.pl

The structure of the title compound, C₅H₅N₂O₂⁺·Cl^-, is composed of chloride anions and 4-carboxypyridazin-1-ium cations. Chloride anions bridge the cations via O-HCl and N-HCl hydrogen bonds to form ribbons. The latter, linked by van der Waals forces with lengths in the range 3.254 (2)-3.497 (2) Å, form coplanar layers. Very weak interactions operate also between adjacent layers, as indicated by their spacing of 3.339 (1) Å.

Related literature

For the crystal structure of pyridazine-3-carboxylic acid hydrochloride, see: Gryz et al. (2003). For a report of molecular layers in the structure of pyrazine-2-carboxylic acid, see: Takusagawa et al. (1974).

Experimental

Crystal data

C₅H₅N₂O₂⁺·Cl^-
M_r = 160.56
Monoclinic, P 2₁ /n
a = 6.8505 (14) Å
b = 6.5905 (13) Å
c = 14.561 (3) Å
= 97.65 (3)°
V = 651.6 (2) Å³
Z = 4
Mo K radiation
= 0.52 mm^-1
T = 293 (2) K
0.39 × 0.16 × 0.12 mm

Data collection

Kuma KM-4 four-circle diffractometer
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ) T_min = 0.942, T_max = 0.952
2062 measured reflections
1917 independent reflections
1318 reflections with I > 2(I)
R_int = 0.024
3 standard reflections every 200 reflections intensity decay: 1.1%

Refinement

R[F² > 2(F²)] = 0.030
wR(F²) = 0.104
S = 1.03
1917 reflections
99 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.35 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H2Cl1	0.91 (3)	2.05 (3)	2.9464 (14)	169 (2)
N1-H1Cl1ⁱ	0.92 (3)	2.15 (3)	3.0373 (15)	160 (2)
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: KM-4 Software (Kuma, 1996 $[Kuma (1996). KM-4 Software. Kuma Diffraction Ltd, Wroclaw, Poland.]$ ); cell refinement: KM-4 Software; data reduction: DATAPROC (Kuma, 2001 $[Kuma (2001). DATAPROC. Kuma Diffraction Ltd, Wroclaw, Poland.]$ ); 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: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RK2101 ).

References

Gryz, M., Starosta, W., Ptasiewicz-Bak, H. & Leciejewicz, J. (2003). J. Coord. Chem. 56, 1505-1511.
Kuma (1996). KM-4 Software. Kuma Diffraction Ltd, Wroclaw, Poland.
Kuma (2001). DATAPROC. Kuma Diffraction Ltd, Wroclaw, Poland.
Oxford Diffraction (2008). CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Takusagawa, F., Higuchi, T. & Shimada, A. (1974). Bull. Chem. Soc. Jpn, 47, 1409-1414.

organic compounds