2,2-Bis(pyridin-2-yl)-1,3-diazinane

Salim F Haddad; Ismail Warad; Shehdeh Jodeh; Taibi Ben Hadda

doi:10.1107/S1600536813007459

. 2013 Mar 23;69(Pt 4):o569. doi: 10.1107/S1600536813007459

2,2-Bis(pyridin-2-yl)-1,3-diazinane

Salim F Haddad ^a,^*, Ismail Warad ^b, Shehdeh Jodeh ^b, Taibi Ben Hadda ^c

PMCID: PMC3629617 PMID: 23634104

Abstract

In the title compound, C₁₄H₁₆N₄, the six-membered hexahydropyrimidine ring adopts a chair conformation. In the crystal, one of the two pyrimidine N atoms engages in N—H⋯N hydrogen bonding with one of the pyridine N atoms, generating a helical chain running along the c axis. The helical pitch is the length of the c axis.

Related literature

For related structures, see: Song et al. (2010 ▶); Jayaratna & Norman (2010 ▶); Fun & Kia (2008 ▶); Warad et al. (2012 ▶). For competition between cyclization and bisimine formation, see: Locke et al. (2009 ▶). For the use of hexahydropyrimidines as polydentate ligands for the synthesis of transition metal coordination complexes, see: Schmidt et al. (2011 ▶).

Experimental

Crystal data

C₁₄H₁₆N₄
M _r = 240.31
Monoclinic,
a = 14.2372 (14) Å
b = 8.0302 (8) Å
c = 11.3277 (9) Å
β = 103.075 (8)°
V = 1261.5 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.3 × 0.2 × 0.15 mm

Data collection

Agilent Xcalibur Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T _min = 0.98, T _max = 0.99
4640 measured reflections
2238 independent reflections
1656 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.108
S = 1.05
2238 reflections
171 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.15 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: SHELXTL (Sheldrick, 2008 ▶) and ORTEP (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Click here for additional data file.^{(23KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813007459/nk2200sup1.cif

e-69-0o569-sup1.cif^{(23KB, cif)}

Click here for additional data file.^{(110KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813007459/nk2200Isup2.hkl

e-69-0o569-Isup2.hkl^{(110KB, hkl)}

Click here for additional data file.^{(5.2KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813007459/nk2200Isup3.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
N3—H3⋯N2ⁱ	0.878 (17)	2.425 (18)	3.2845 (19)	166.4 (15)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The X-ray structural work was done at Hamdi Mango Center for Scientific research at The University of Jordan, Amman 11942, Jordan.

supplementary crystallographic information

Comment

Condensation of 1,3-diamines with 2-dipyridlketone is a well documented reaction for two potential products, hexahydropyrimidine and classical Schiff bases compounds (Warad et al., 2012; Song et al., 2010; Jayaratna & Norman, 2010; Fun & Kia, 2008). Both of these products are extensively utilized as polydentate ligands to synthesize coordination metal complexes. The title compound was obtained during our attempt to synthesize novel ligands in order to study their coordination chemistry.

The pyrimidine ring in the molecule assumes a chair configuration allowing better disposition for H-bonding. The molecular units are connected via hydrogen bonding between one pyrimidine nitrogen atom, N3 and one pyridinic nitrogen atom, N2 in adjacent molecule as shown in Fig. 2. Hydrogen bond values are tabulated.

Experimental

A solution of 2-dipyridlketone (0.25 g, 1.45 mmol) in anhydrous ethanol (20 ml) was mixed with 1,3-propanediamine (0.16 ml, 1.5 mmoL) and allowed to reflux for about four hours. The resulting mixture was concentrated under reduced pressure and the title compound was precipitated by the addition of 40 ml of ice cool distilled water. The precipitate was filtered off, washed three times with 40 ml of distilled water, recrystallized in ethanol and allowed to stand at room temperature. After three days, colourless crystals suitable for single-crystal X-ray data collection were obtained (0.24 g, yield 77%).