(IUCr) 2-(1H-Pyrazol-3-yl)pyridinium chloride monohydrate

Volume 65
Part 8
Pages o1962-o1963
August 2009

Received 15 July 2009
Accepted 17 July 2009
Online 25 July 2009

Key indicators
Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.002 Å
R = 0.048
wR = 0.162
Data-to-parameter ratio = 35.7
Details

2-(1H-Pyrazol-3-yl)pyridinium chloride monohydrate

Tatiana R. Amarante,^a Isabel S. Gonçalves ^a and Filipe A. Almeida Paz ^a ^*

^aDepartment of Chemistry, University of Aveiro, CICECO, 3810-193 Aveiro, Portugal
Correspondence e-mail: filipe.paz@ua.pt

The title organic salt, C₈H₈N₃⁺·Cl^-·H₂O, exhibits a rich hydrogen-bonding network involving all constituent species. The water molecules are engaged in strong O-HCl interactions with the chloride anions, two neighboring protonated 2-(1H-pyrazol-3-yl)pyridinium species interact via N-HN bonds with two pyrazole rings. Further, a short and highly directional C-HO interaction is observed connecting the pyridinium ring to the water molecule of crystallization. Weak C-HCl and N-HCl interactions contribute to the stabilization of the crystal structure.

Related literature

For related structures with 2-(3-pyrazolyl)pyridine or its derivatives, see: Coelho et al. (2006, 2007); Fleming et al. (1998); Jones et al. (1997); Lam et al. (1997); Leita et al. (2004); Li (2007); Liu et al. (2006); Mokuolu et al. (2007); Hu, Li et al. (2006); Hu, Wang et al. (2006); Hu et al. (2008); Huo et al. (2006); Ward, Fleming et al. (1998); Ward, Mann et al. (1998). For detailed background to the role of hydrogen bonds in the supramolecular organization of organic crystals, see: Nangia & Desiraju (1998). For general background studies on crystal engineering approaches from our research group, see: Paz & Klinowski (2003); Paz et al. (2002). For a description of the graph-set notation for hydrogen-bonded aggregates, see: Bernstein et al. (1995). For a description of the Cambridge Structural Database, see: Allen (2002).

Experimental

Crystal data

C₈H₈N₃⁺·Cl^-·H₂O
M_r = 199.64
Triclinic, $[P \overline 1]$
a = 6.8487 (2) Å
b = 8.3523 (3) Å
c = 9.0843 (3) Å
= 114.693 (1)°
= 99.867 (2)°
= 91.097 (2)°
V = 462.75 (3) Å³
Z = 2
Mo K radiation
= 0.38 mm^-1
T = 150 K
0.18 × 0.15 × 0.09 mm

Data collection

Bruker X8 Kappa CCD APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1997) T_min = 0.930, T_max = 0.951
26245 measured reflections
4422 independent reflections
3687 reflections with I > 2(I)
R_int = 0.024

Refinement

R[F² > 2(F²)] = 0.048
wR(F²) = 0.162
S = 1.07
4422 reflections
124 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 1.26 e Å^-3
_min = -0.99 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1N2ⁱ	0.88	2.25	2.9502 (16)	137
O1W-H1ACl1ⁱⁱ	0.940 (19)	2.176 (10)	3.1113 (13)	173 (2)
O1W-H1BCl1	0.95 (2)	2.279 (11)	3.2106 (12)	170 (2)
C5-H5O1Wⁱⁱⁱ	0.95	0	2.7203 (16)	156
C8-H8Cl1^iv	0.95	0	3.5862 (18)	137
N3-H3Cl1^v	0.88	2.94	3.7915 (15)	162
C2-H2Cl1^v	0.95	0	3.5604 (13)	159
C6-H6Cl1^vi	0.95	0	3.5329 (14)	127
C7-H7Cl1^vi	0.95	0	3.5649 (14)	123
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x+1, -y+1, -z; (iii) x, y-1, z; (iv) x+1, y, z; (v) -x+2, -y+1, -z+1; (vi) -x+2, -y, -z.

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT-Plus (Bruker, 2005); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2009); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2502 ).

Acknowledgements

We are grateful to Fundação para a Ciência e a Tecnologia (FCT, Portugal) for their general financial support (Project PTDC/QUI/71198/2006) and also for specific funding toward the purchase of the single-crystal diffractometer.

References

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organic compounds