Crystal structure of 2,2-dimethyl-N-(pyridin-3-yl)propanamide

Gamal A El-Hiti; Keith Smith; Amany S Hegazy; Saud A Alanazi; Benson M Kariuki

doi:10.1107/S2056989015005289

. 2015 Mar 21;71(Pt 4):o246–o247. doi: 10.1107/S2056989015005289

Crystal structure of 2,2-dimethyl-N-(pyridin-3-yl)propanamide

Gamal A El-Hiti ^a,^*, Keith Smith ^b, Amany S Hegazy ^b, Saud A Alanazi ^a, Benson M Kariuki ^b,^*

PMCID: PMC4438820 PMID: 26029437

Abstract

In the title compound, C₁₀H₁₄N₂O, the pyridine ring is inclined to the mean plane of the amide moiety [N—C(=O)C] by 17.60 (8)°. There is an intramolecular C—H⋯O hydrogen bond present involving the carbonyl O atom. In the crystal, molecules are linked via N—H⋯N hydrogen bonds, forming chains propagating along [100]. The tert-butyl group is disordered over two sets of sites with a refined occupancy ratio of 0.758 (12):0.242 (12).

Keywords: crystal structure, pyridine, propanamide, N—H⋯N hydrogen bonds

Related literature

For related biologically active pyridine derivatives, see: de Candia et al. (2013 ▸); Thorat et al. (2013 ▸); Abdel-Megeed et al. (2012 ▸). For pyridine ring-system modifications, see: El-Hiti et al. (2015 ▸); Smith et al. (2012 ▸, 2013 ▸); Londregan et al. (2009 ▸); Joule & Mills (2000 ▸); Turner (1983 ▸). For the crystal structures of related compounds, see: El-Hiti et al. (2014 ▸); Seidler et al. (2011 ▸); Koch et al. (2008 ▸); Mazik et al. (2004 ▸). graphic file with name e-71-0o246-scheme1.jpg

Experimental

Crystal data

C₁₀H₁₄N₂O
M _r = 178.23
Orthorhombic,
a = 11.2453 (3) Å
b = 10.5272 (3) Å
c = 17.5339 (6) Å
V = 2075.69 (11) Å³
Z = 8
Cu Kα radiation
μ = 0.60 mm⁻¹
T = 293 K
0.23 × 0.19 × 0.06 mm

Data collection

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014 ▸) T _min = 0.840, T _max = 1.000
7164 measured reflections
2065 independent reflections
1722 reflections with I > 2σ(I)
R _int = 0.017

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.127
S = 1.05
2065 reflections
153 parameters
114 restraints
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2014 ▸); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: WinGX (Farrugia, 2012 ▸).

Supplementary Material

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S2056989015005289/su5094sup1.cif

e-71-0o246-sup1.cif^{(273.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015005289/su5094Isup2.hkl

e-71-0o246-Isup2.hkl^{(113.7KB, hkl)}

Click here for additional data file.^{(4KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015005289/su5094Isup3.cml

Click here for additional data file.^{(1.1MB, tif)}

t . DOI: 10.1107/S2056989015005289/su5094fig1.tif

The molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level. Only the major component of the disordered t-butyl group is shown.

Click here for additional data file.^{(1.9MB, tif)}

b t . DOI: 10.1107/S2056989015005289/su5094fig2.tif

Crystal packing of the title compound, viewed along the b axis, with the N—H⋯N interactions shown as dashed lines (see Table 1 for details). The minor component of the disordered t-butyl group has been omitted for clarity.

CCDC reference: 1054113

Additional supporting information: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (, ).

DHA	DH	HA	D A	DHA
C2H2O1	0.93	2.25	2.8263(18)	119
N1H1N2ⁱ	0.86	2.17	3.0012(15)	164

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors extend their appreciation to the Cornea Research Chair, Department of Optometry, College of Applied Medical Sciences, King Saud University, for funding this research, and to Cardiff University for continued support.

supplementary crystallographic information

S1. Introduction

Pyridine derivatives are interesting compounds (Joule & Mills, 2000) since they show a range of biological activities (Thorat et al., 2013) such as anticoagulant (de Candia et al., 2013) and antimicrobial (Abdel-Megeed et al., 2012) properties. Various simple and efficient processes have been developed for modification of the pyridine ring system (El-Hiti et al., 2015; Smith et al., 2013, Smith et al., 2012, Londregan et al., 2009; Turner, 1983). The X-ray crystal structures of related compounds have been reported (El-Hiti et al., 2014; Seidler et al., 2011; Koch et al., 2008; Mazik et al., 2004).

S2. Experimental

The title compound was obtained in 73% yield from the reaction of 3-aminopyridine with pivaloyl chloride in the presence of triethylamine in dichloromethane at 273 K for 15 min and then at room temperature for 2 h (Turner, 1983). Crystallization from a mixture of ethyl acetate and hexane gave colourless crystals of the title compound. The spectroscopic and analytical data for the title compound were identical with those reported previously (Turner, 1983)

S2.1. Refinement

The N- and C-bound H atoms were included in calculated positions and refined as riding: N—H = 0.86 Å, C—H = 0.93 - 0.98 Å with U_iso(H) = 1.5U_eq(C) for methyl H atoms and = 1.2U_eq(C) for other H atoms. The t-butyl group is disordered over two sites and was refined with bond length constraints to give a refined occupancy ratio of 0.758 (12):0.242 (12).

S3. Results and discussion

The molecular structure of the title compound is illustrated in Fig. 1. The pyridine ring is inclined to the mean plane of the amide moiety [N1—C6(═ O1)—C7] by 17.60 (8) °. There is an intramolecular C—H···O hydrogen bond present involving the carbonyl O atom (Table 1).

In the crystal, molecules are linked via N—H···N hydrogen bonds forming chains propagating along [100]; see Table 1 and Fig. 2.