8-Quinolylguanidinium chloride

Chang-Mei Wei

doi:10.1107/S1600536808013640

. 2008 Jun 7;64(Pt 7):o1244. doi: 10.1107/S1600536808013640

8-Quinolylguanidinium chloride

Chang-Mei Wei ^a,^*

PMCID: PMC2961674 PMID: 21202879

Abstract

The title compound, C₁₀H₁₁N₄ ⁺·Cl⁻, has been synthesized by the reaction of 8-aminoquinoline and cyanamide. The dihedral angle between the plane of the guanidine group and the quinoline ring system is 68.64 (13)°. The crystal structure is stabilized by intermolecular N—H⋯Cl hydrogen bonds.

Related literature

For related literature, see: Hughes & Liu (1976 ▶); Juyal & Anand (2003 ▶); Knhla et al. (1986 ▶); Orner & Hamilton (2001 ▶).

Experimental

Crystal data

C₁₀H₁₁N₄ ⁺·Cl⁻
M _r = 222.68
Orthorhombic,
a = 8.7410 (17) Å
b = 9.0230 (18) Å
c = 13.942 (3) Å
V = 1099.6 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 293 (2) K
0.20 × 0.20 × 0.20 mm

Data collection

Siemens P4 diffractometer
Absorption correction: multi-scan (XPREP in SHELXTL; Sheldrick, 2008 ▶) T _min = 0.939, T _max = 0.969
3398 measured reflections
2398 independent reflections
2340 reflections with I > 2σ(I)
R _int = 0.0301
3 standard reflections every 97 reflections intensity decay: 2.1%

Refinement

R[F ² > 2σ(F ²)] = 0.062
wR(F ²) = 0.108
S = 0.99
2398 reflections
136 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.28 e Å⁻³
Absolute structure: Flack (1983 ▶), 500 Friedel pairs
Flack parameter: 0.02 (10)

Data collection: XSCANS (Bruker, 2000 ▶); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 2008 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808013640/rz2213sup1.cif

e-64-o1244-sup1.cif^{(14.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808013640/rz2213Isup2.hkl

e-64-o1244-Isup2.hkl^{(117.9KB, 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
N1—H1A⋯Cl1ⁱ	0.86	2.34	3.171 (3)	162
N2—H2A⋯Cl1ⁱ	0.86	2.65	3.401 (3)	146
N2—H2B⋯Cl1ⁱⁱ	0.86	2.64	3.405 (3)	149
N3—H3A⋯Cl1ⁱⁱ	0.86	2.39	3.198 (3)	158
N3—H3B⋯Cl1	0.86	2.46	3.269 (3)	156

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

Acknowledgments

The author is grateful to the Science Foundation of Jiangsu Education Bureau (05KJD 150039), the Professor Foundation of Huaiyin Teachers College (05 HSJS018) and the Science Foundation of Jangsu Key Laboratory for the Chemistry of Low-Dimensional Materials (JSKC 06028) for financial support.

supplementary crystallographic information

Comment

Guanidine is used in variety of supramolecular recognition processes across the spectrum of organic, biological and medicinal chemistry (Orner & Hamilton, 2001). Guanidine compounds containing a quinolyl ring are used as decongestive agents (Hughes & Liu, 1976) and in the treatment of gastrointestinal motility disorders (Knhla et al., 1986). Guanidine derivatives are also employed as inhibitors of the reactions responsible for sedimentation in fuels as they efficiently disperse the gum and sediments formed (Juyal & Anand, 2003). These important compounds are therefore of interest from a structural viewpoint. In this paper, we report the crystal structure of the title compound, (I), which, to our knowledge, represents the first structure containing the 8-quinolylguanidium cation. A perspective view of (I) is shown in Fig.1. In (I), bond lengths and angles within the 8-quinolylguanidium cation (Table 1) indicate a partial conjugation between the guanidine group and the quinoline ring. The dihedral angle formed by the plane of the guanidine group and the quinoline ring is 68.64 (13)°. In the crystal packing, The chloride anion interacts with the cations though N—H···Cl hydrogen bonds forming a three dimensions network (Fig. 2, Table 2).

Experimental

The title compound was synthesized as following. A mixture of 8-aminoquinoline (68.06 mmol), cyanamide (83.3 mmol) and ethanol (50 ml) was heated under reflux for 3 h with stirring. The reaction mixture was evaporated to give a residue. Singles crystals suitable for X-ray analysis were obtained by slow evaporation of an aqueous solution.