3-(2,6-Dimethyl­anilino)imidazo[1,2-a]pyridin-1-ium perchlorate

Gary S Nichol; Anuj Sharma; Hong-Yu Li

doi:10.1107/S1600536811014735

. 2011 Apr 29;67(Pt 5):o1224. doi: 10.1107/S1600536811014735

3-(2,6-Dimethylanilino)imidazo[1,2-a]pyridin-1-ium perchlorate

Gary S Nichol ^a,^*, Anuj Sharma ^b, Hong-Yu Li ^b

PMCID: PMC3089197 PMID: 21754522

Abstract

The structure of the organic cation in the title compound, C₁₅H₁₆N₃ ⁺·ClO₄ ⁻, contains two essentially planar rings. Mean planes fitted through all non-H atoms of each ring system have an r.m.s. deviation of 0.019 Å for the imidazole-based ring and 0.016 Å for the 2,6-dimethylphenyl ring. The angle between the two planes is 86.76 (2)°. In the crystal structure, N—H⋯O interactions form a one-dimensional chain, which propagates in the b-axis direction. C—H⋯O interactions are also found in the crystal packing.

Related literature

For background information on the Groebke–Blackburn synthesis, see: Bienaymé & Bouzid (1998 ▶); Blackburn et al. (1998 ▶); Groebke et al. (1998 ▶). For details of the chemical synthesis, see: Nichol et al. (2011 ▶); Sharma & Li (2011 ▶). For information on graph-set notation to describe hydrogen-bonding motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₅H₁₆N₃ ⁺·ClO₄ ⁻
M _r = 337.76
Triclinic,
a = 8.6347 (3) Å
b = 8.7663 (3) Å
c = 11.5155 (4) Å
α = 70.668 (2)°
β = 73.131 (2)°
γ = 72.679 (2)°
V = 767.24 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 100 K
0.26 × 0.16 × 0.16 mm

Data collection

Bruker Kappa APEXII DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.932, T _max = 0.957
27864 measured reflections
8640 independent reflections
6871 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.111
S = 1.05
8640 reflections
272 parameters
All H-atom parameters refined
Δρ_max = 0.61 e Å⁻³
Δρ_min = −0.51 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXTL and publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811014735/kj2175sup1.cif

e-67-o1224-sup1.cif^{(24.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811014735/kj2175Isup2.hkl

e-67-o1224-Isup2.hkl^{(422.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811014735/kj2175Isup3.cdx

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—H2N⋯O1ⁱ	0.869 (16)	1.955 (17)	2.8169 (10)	170.8 (15)
N3—H3N⋯O3	0.832 (16)	2.216 (15)	2.8899 (10)	138.3 (14)
C2—H2⋯O2ⁱⁱ	0.911 (14)	2.547 (14)	3.3826 (11)	152.8 (12)
C3—H3⋯O4ⁱⁱ	0.971 (15)	2.559 (15)	3.2893 (12)	132.0 (11)

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

Acknowledgments

The diffractometer was purchased with funding from NSF grant No. CHE-0741837.

supplementary crystallographic information

Comment

The Groebke–Blackburn reaction is the most popular way to prepare imidazo-azines from 2-aminoazines in a single-step (Groebke et al., 1998; Bienaymé & Bouzid, 1998; Blackburn et al., 1998). We have recently reported developments on this synthetic method (Nichol et al., 2011; Sharma & Li, 2011) and present here the crystal structure of the title compound, determined as part of a larger study.

The asymmetric unit of the title compound is shown in Fig. 1. Molecular dimensions are unexceptional. Both ring systems are essentially planar (a mean plane fitted through atoms N1, N2, N3 C1 > C7 has an r.m.s. deviation of 0.019 Å; a mean plane fitted through atoms N3, C8 > C15 has an r.m.s. deviation of 0.016 Å) and the angle between both planes is 86.76 (2)°.

In the crystal, N—H···O interactions form a one-dimensional C²₂(9) chain (Bernstein et al. 1995), which propagates in the b-axis direction (Fig. 2). C—H···O interactions are also found in the crystal packing.

Experimental

The synthesis is described in Sharma & Li (2011).