Pyridine-4-carboximidamidate chloride

Ping Fan; Lei Wang; Huidong Zhang

doi:10.1107/S160053680903517X

. 2009 Sep 9;65(Pt 10):o2408. doi: 10.1107/S160053680903517X

Pyridine-4-carboximidamidate chloride

Ping Fan ^a,^*, Lei Wang ^a, Huidong Zhang ^b

PMCID: PMC2970348 PMID: 21577868

Abstract

In the title salt, C₆H₈N₃ ⁺·Cl⁻, each pyridinecarboximidamidate cation is linked to two symmetry-related cations through N—H⋯N hydrogen bonds, and to two chloride ions by N—H⋯Cl hydrogen bonds. The N—H⋯N hydrogen bonds involve the pyridine N atom and one NH₂ group. In the crystal, N—H⋯N and N—H⋯Cl hydrogen bonds extend the structure into two-dimensional layers. Weak C—H⋯Cl interactions further connect these layers into a three-dimensional network.

Related literature

For background, see: Chudinov et al. (2005 ▶); Kamei et al. (2005 ▶).

Experimental

Crystal data

C₆H₈N₃ ⁺·Cl⁻
M _r = 157.60
Orthorhombic,
a = 7.3928 (13) Å
b = 10.4467 (16) Å
c = 18.925 (3) Å
V = 1461.6 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.44 mm⁻¹
T = 293 K
0.37 × 0.32 × 0.21 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.853, T _max = 0.911
1949 measured reflections
1435 independent reflections
1215 reflections with I > 2σ(I)
R _int = 0.018

Refinement

R[F ² > 2σ(F ²)] = 0.033
wR(F ²) = 0.092
S = 1.04
1435 reflections
124 parameters
All H-atom parameters refined
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; 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 Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680903517X/bh2242sup1.cif

e-65-o2408-sup1.cif^{(12.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680903517X/bh2242Isup2.hkl

e-65-o2408-Isup2.hkl^{(70.9KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯N1ⁱ	0.88 (2)	2.22 (2)	3.058 (2)	160 (2)
N2—H2B⋯Cl1	0.83 (2)	2.79 (2)	3.476 (2)	142 (2)
N3—H3A⋯Cl1	0.93 (2)	2.19 (2)	3.100 (2)	167 (2)
N3—H3B⋯Cl1ⁱⁱ	0.89 (2)	2.41 (2)	3.270 (2)	161 (2)
C5—H5⋯Cl1ⁱⁱⁱ	0.90 (2)	2.68 (2)	3.556 (2)	166 (2)

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

supplementary crystallographic information

Comment

The title compound, also known as isonicotinamidine hydrochloride, served as a key intermediate in the synthesis of pharmacologically active compounds. It had attracted a great deal of interest during recent years. A series of new piperidinyl- and 1,2,3,6-tetrahydropyridinylpyrimidine derivatives was synthesized by using isonicotinamidine as an important intermediate. Isonicotinamidine has a unique structure and exists in the form of hydrochloride or acetate (Chudinov et al., 2005; Kamei et al., 2005).

The title compound is an organic salt (Fig. 1). In the cation, dihedral angle between the pyridyl ring and the plane confined by N2, N3 and C6 is 42.1°. Each isonicotinamidine cation is connected to two other cations by N—H···N hydrogen bonds, and to two Cl^- anions by N—H···Cl hydrogen bonds (Fig. 2), to form two dimensional layers including one-dimensional zigzag chains (Fig. 3). Weak C—H···Cl interactions [C···Cl = 3.556 (2) Å] link these layers to provide a three-dimensional supramolecular network.

Experimental

The title compound was prepared according to the method of Kamei et al. (2005). Block-shaped crystals suitable for X-ray diffraction were obtained from ethanol/acetone.