N,N,N′,N′-Tetra­isobutyl­pyridine-2,6-dicarboxamide

Michaela Pojarová; Michal Dušek; Emanuel Makrlík; Vasily A Babain; Petr Vaňura

doi:10.1107/S1600536811040608

. 2011 Oct 8;67(Pt 11):o2896–o2897. doi: 10.1107/S1600536811040608

N,N,N′,N′-Tetraisobutylpyridine-2,6-dicarboxamide

Michaela Pojarová ^a,^*, Michal Dušek ^a, Emanuel Makrlík ^b, Vasily A Babain ^c, Petr Vaňura ^d

PMCID: PMC3247313 PMID: 22219931

Abstract

In the title compound, C₂₃H₃₉N₃O₂, the amide O atoms are displaced by 1.020 (1) and 1.211 (1) Å from the mean plane of the central pyridine ring. In the crystal, molecules are connected by weak C—H⋯O hydrogen bonds between methylene groups in the isobutyl substituents and the amide O atoms.

Related literature

The title compound has been investigated for its extractive properties towards trivalent metals in a synergistic mixture with chlorinated cobalt dicarbollide. For further information, see: Alyapyshev et al. (2004 ▶, 2006 ▶); Romanovskiy et al. (2006 ▶); Babain et al. (2007 ▶); Makrlík et al. (2009 ▶, 2011 ▶). For further synthetic details, see: Nikitskaya et al. (1958 ▶); Shimada et al. (2004 ▶).

Experimental

Crystal data

C₂₃H₃₉N₃O₂
M _r = 389.57
Monoclinic,
a = 10.5247 (2) Å
b = 17.7765 (3) Å
c = 12.8773 (2) Å
β = 96.877 (2)°
V = 2391.91 (7) Å³
Z = 4
Cu Kα radiation
μ = 0.54 mm⁻¹
T = 120 K
0.49 × 0.42 × 0.23 mm

Data collection

Agilent Xcalibur Atlas Gemini ultra diffractometer
Absorption correction: analytical (CrysAlis PRO; Agilent, 2011 ▶) T _min = 0.929, T _max = 0.962
31214 measured reflections
4272 independent reflections
3867 reflections with I > 2σ(I)
R _int = 0.039

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.112
S = 1.05
4272 reflections
261 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶) and DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811040608/hb6423sup1.cif

e-67-o2896-sup1.cif^{(21.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811040608/hb6423Isup2.hkl

e-67-o2896-Isup2.hkl^{(209.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811040608/hb6423Isup3.cml

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
C7—H7A⋯O2ⁱ	0.97	2.57	3.5226 (15)	166
C11—H11A⋯O1ⁱⁱ	0.97	2.55	3.4790 (15)	160

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

Acknowledgments

This study was supported financially by the Institutional Research Plan No. AVOZ10100521 of the Institute of Physics, the project Praemium Academiae of the Academy of Science of the Czech Republic and by the Grant Agency of Faculty of Environmental Sciences, Czech University of Life Sciences, Prague (project No. 42900/1312/3114 "Environmental Aspects of Sustainable Developement of Society") and by the Czech Ministry of Education, Youth and Sports (project MSM 6046137307).

supplementary crystallographic information

Comment

The title compound, (I), shown in Figure 1 and Scheme 1, has been investigated in a synergistic mixtures with the dicarbollylcobaltate anion and its halogen derivatives for significant extraction properties towards trivalent metal cations (Alyapyshev et al.,2004). It consists of pyridine ring with a di-isobutylamide groups in position 2 and 6. This molecule lacks of crystallographic symmetry and the asymmetric unit contains one molecule. While at first impression, the amide groups seem to be related by a mirror plane, closer look reveales their differences. The carbon atoms of carbonyl groups do not lay in a plane of the pyridine ring and they differ in the distance to this plane (0.062 Å for C6 and 0.234 Å for C15). The molecules form bands along the c axis (Fig. 2) via system of hydrogen bonds (Table 1).

Experimental

The title compound was synthesized as described in Shimada et al. (2004), and Nikitskaya et al. (1958). Colourless prisms were prepared by slow evaporation from an acetonitrile solution.