Acta Cryst. (2008). E64, o1553 [ doi:10.1107/S1600536808022319 ]
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-H
Cl 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.
Single crystals of I were obtained by recrystallization of pyridazine–4–carboxylic acid (ALDRICH) from warm 1M solution of hydrochloric acid. Attempts to recrystallize from water and alcohols yielded specimens unsuitable for collecting X–ray data.
All H atoms bonded with C atoms were positioned geometrically and refined in riding model approximation with C—H = 0.93Å and Uiso(H) = 1.2Ueq(C). The H atoms connected with N and O atoms were located in difference Fourier map and refined isotropically.
Data collection: KM-4 Software (Kuma, 1996); cell refinement: KM-4 Software (Kuma, 1996); data reduction: DATAPROC (Kuma, 2001); 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 (Sheldrick, 2008).
![[Figure 1]](./rk2101fig1thm.gif)
| Fig. 1. A molecular structure of I with the atom labelling scheme. The displacement ellipsoids are drawn at 50% probability level. H atoms are presented as a small spheres of arbitrary radius. |
![[Figure 2]](./rk2101fig2thm.gif)
| Fig. 2. The structure packing diagram of I. |
| C5H5N2O2+·Cl– | F000 = 328 |
| Mr = 160.56 | Dx = 1.637 Mg m−3 |
| Monoclinic, P21/n | Mo Kα radiation λ = 0.71073 Å |
| a = 6.8505 (14) Å | Cell parameters from 6 reflections |
| b = 6.5905 (13) Å | θ = 6–15º |
| c = 14.561 (3) Å | µ = 0.52 mm−1 |
| β = 97.65 (3)º | T = 293 (2) K |
| V = 651.6 (2) Å3 | Block, colourless |
| Z = 4 | 0.39 × 0.16 × 0.12 mm |
| Kuma KM-4 four-circle diffractometer | Rint = 0.024 |
| Radiation source: Fine–focus sealed tube | θmax = 30.1º |
| Monochromator: Graphite | θmin = 2.8º |
| T = 293(2) K | h = −9→0 |
| Profile data from ω/2θ scans | k = 0→9 |
| Absorption correction: Analytical (CrysAlis RED; Oxford Diffraction, 2008) | l = −20→20 |
| Tmin = 0.942, Tmax = 0.952 | 3 standard reflections |
| 2062 measured reflections | every 200 reflections |
| 1917 independent reflections | intensity decay: 1.2% |
| 1318 reflections with I > 2σ(I) |
| Refinement on F2 | Secondary atom site location: Difmap |
| Least-squares matrix: Full | Hydrogen site location: Geom |
| R[F2 > 2σ(F2)] = 0.030 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.104 | w = 1/[σ2(Fo2) + (0.0577P)2 + 0.1527P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.03 | (Δ/σ)max = 0.001 |
| 1917 reflections | Δρmax = 0.36 e Å−3 |
| 99 parameters | Δρmin = −0.21 e Å−3 |
| Primary atom site location: Direct | Extinction correction: None |
| C5H5N2O2+·Cl– | V = 651.6 (2) Å3 |
| Mr = 160.56 | Z = 4 |
| Monoclinic, P21/n | Mo Kα |
| a = 6.8505 (14) Å | µ = 0.52 mm−1 |
| b = 6.5905 (13) Å | T = 293 (2) K |
| c = 14.561 (3) Å | 0.39 × 0.16 × 0.12 mm |
| β = 97.65 (3)º |
| Kuma KM-4 four-circle diffractometer | 1318 reflections with I > 2σ(I) |
| Absorption correction: Analytical (CrysAlis RED; Oxford Diffraction, 2008) | Rint = 0.024 |
| Tmin = 0.942, Tmax = 0.952 | 3 standard reflections |
| 2062 measured reflections | every 200 reflections |
| 1917 independent reflections | intensity decay: 1.2% |
| R[F2 > 2σ(F2)] = 0.030 | 99 parameters |
| wR(F2) = 0.104 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.03 | Δρmax = 0.36 e Å−3 |
| 1917 reflections | Δρmin = −0.21 e Å−3 |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. |
Refinement. Refinement of F^2^ against ALL reflections. The weighted R–factor wR and goodness of fit S are based on F^2^, conventional R–factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > σ(F^2^) is used only for calculating R–factors(gt) etc. and is not relevant to the choice of reflections for refinement. R–factors based on F^2^ are statistically about twice as large as those based on F, and R–factors based on ALL data will be even larger. |
| x | y | z | Uiso*/Ueq | ||
| Cl1 | 0.61082 (6) | 0.18289 (6) | 0.39362 (3) | 0.03696 (13) | |
| O1 | 0.8041 (2) | 0.6663 (2) | 0.46266 (8) | 0.0485 (3) | |
| C3 | 0.8870 (3) | 0.9337 (3) | 0.61752 (11) | 0.0382 (4) | |
| H3 | 0.8395 | 0.9943 | 0.5613 | 0.046* | |
| C4 | 0.8811 (2) | 0.7225 (2) | 0.62339 (10) | 0.0296 (3) | |
| O2 | 0.7273 (2) | 0.4276 (2) | 0.56133 (8) | 0.0414 (3) | |
| C7 | 0.7988 (2) | 0.6028 (3) | 0.53974 (10) | 0.0330 (3) | |
| C5 | 0.9550 (2) | 0.6321 (2) | 0.70515 (11) | 0.0337 (3) | |
| H5 | 0.9548 | 0.4918 | 0.7120 | 0.040* | |
| N2 | 0.9559 (2) | 1.0516 (2) | 0.68707 (10) | 0.0414 (3) | |
| C6 | 1.0306 (3) | 0.7589 (3) | 0.77771 (11) | 0.0376 (4) | |
| H6 | 1.0841 | 0.7045 | 0.8345 | 0.045* | |
| N1 | 1.0257 (2) | 0.9555 (2) | 0.76522 (10) | 0.0368 (3) | |
| H1 | 1.063 (3) | 1.042 (4) | 0.8143 (17) | 0.063 (7)* | |
| H2 | 0.675 (4) | 0.358 (4) | 0.5097 (19) | 0.069 (8)* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cl1 | 0.0472 (2) | 0.02641 (19) | 0.0353 (2) | 0.00189 (16) | −0.00212 (15) | −0.00355 (14) |
| O1 | 0.0698 (9) | 0.0472 (8) | 0.0264 (6) | 0.0011 (7) | −0.0010 (5) | 0.0038 (5) |
| C3 | 0.0507 (10) | 0.0319 (8) | 0.0309 (7) | 0.0058 (7) | 0.0017 (7) | 0.0058 (6) |
| C4 | 0.0313 (7) | 0.0310 (7) | 0.0259 (6) | 0.0027 (6) | 0.0021 (5) | 0.0015 (5) |
| O2 | 0.0567 (8) | 0.0354 (6) | 0.0303 (6) | −0.0046 (6) | −0.0010 (5) | −0.0028 (5) |
| C7 | 0.0371 (8) | 0.0336 (8) | 0.0267 (7) | 0.0064 (6) | −0.0017 (6) | 0.0005 (6) |
| C5 | 0.0406 (8) | 0.0291 (7) | 0.0295 (7) | 0.0003 (6) | −0.0025 (6) | 0.0030 (5) |
| N2 | 0.0554 (9) | 0.0296 (7) | 0.0386 (7) | 0.0022 (7) | 0.0041 (6) | 0.0022 (5) |
| C6 | 0.0463 (9) | 0.0349 (8) | 0.0288 (7) | −0.0010 (7) | −0.0045 (6) | 0.0028 (6) |
| N1 | 0.0443 (8) | 0.0340 (7) | 0.0315 (6) | −0.0034 (6) | 0.0023 (5) | −0.0034 (5) |
| O1—C7 | 1.203 (2) | O2—H2 | 0.91 (3) |
| C3—N2 | 1.313 (2) | C5—C6 | 1.392 (2) |
| C3—C4 | 1.395 (2) | C5—H5 | 0.9300 |
| C3—H3 | 0.9300 | N2—N1 | 1.334 (2) |
| C4—C5 | 1.367 (2) | C6—N1 | 1.308 (2) |
| C4—C7 | 1.497 (2) | C6—H6 | 0.9300 |
| O2—C7 | 1.309 (2) | N1—H1 | 0.92 (3) |
| N2—C3—C4 | 123.60 (15) | C4—C5—C6 | 117.17 (16) |
| N2—C3—H3 | 118.2 | C4—C5—H5 | 121.4 |
| C4—C3—H3 | 118.2 | C6—C5—H5 | 121.4 |
| C5—C4—C3 | 118.55 (15) | C3—N2—N1 | 115.32 (14) |
| C5—C4—C7 | 122.31 (15) | N1—C6—C5 | 119.27 (15) |
| C3—C4—C7 | 119.12 (14) | N1—C6—H6 | 120.4 |
| C7—O2—H2 | 111.4 (17) | C5—C6—H6 | 120.4 |
| O1—C7—O2 | 126.14 (16) | C6—N1—N2 | 126.06 (15) |
| O1—C7—C4 | 121.39 (16) | C6—N1—H1 | 120.2 (16) |
| O2—C7—C4 | 112.47 (13) | N2—N1—H1 | 113.5 (16) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O2—H2···Cl1 | 0.91 (3) | 2.05 (3) | 2.9464 (14) | 169 (2) |
| N1—H1···Cl1i | 0.92 (3) | 2.15 (3) | 3.0373 (15) | 160 (2) |
| Symmetry codes: (i) x+1/2, −y+3/2, z+1/2. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O2—H2···Cl1 | 0.91 (3) | 2.05 (3) | 2.9464 (14) | 169 (2) |
| N1—H1···Cl1i | 0.92 (3) | 2.15 (3) | 3.0373 (15) | 160 (2) |
| Symmetry codes: (i) x+1/2, −y+3/2, z+1/2. |
Gryz, M., Starosta, W., Ptasiewicz-Bąk, H. & Leciejewicz, J. (2003). J. Coord. Chem. 56, 1505–1511.
Kuma (1996). KM-4 Software. Kuma Diffraction Ltd, Wrocław, Poland.
Kuma (2001). DATAPROC. Kuma Diffraction Ltd, Wrocław, 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.
The structure of the title compound (C5H5N2O2)+ Cl-, I, is built from chloride anions and heterocycle cations. Chloride anions bridge the cations via hydrogen bonds O2—H2···Cl1 2.05 (3)Å and N1—H1···Cl1i 2.15 (3)Å to form ribbons; symmetry code: (i) x+1/2, -y+3/2, z+1/2. The ribbons linked by van der Waals forces with lengths in the range from 3.254 (2) to 3.497 (2)Å make coplanar layers. The shortest distance between pyridazine rings belonging to adjacent layers is 3.339 (1)Å. The pyridazine ring are planar (r.m.s. 0.0060Å) and formes with the carboxylate group (C7/O1/O2) dihedral angle 27.7 (1)°. Bond lengths and bond angles within the cation agree well with those reported in the structure of pyridazine–3–carboxylic acid hydrochloride (Gryz et al., 2003).