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Volume 69 
Part 4 
Page o569  
April 2013  

Received 10 February 2013
Accepted 18 March 2013
Online 23 March 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.041
wR = 0.108
Data-to-parameter ratio = 13.1
Details
Open access

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

aDepartment of Chemistry, The University of Jordan, Amman 11942, Jordan,bDepartment of Chemistry, An-Najah National University, Nablus, Palestinian Territories, and cLaboratoire LCM, Faculté Sciences, Université Mohammed Ier, Oujda 60000, Morocco
Correspondence e-mail: hadsal2003@yahoo.com

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[Song, X.-P., Li, G.-C., Wu, C.-Z. & Yang, F.-L. (2010). Acta Cryst. E66, o1083.]); Jayaratna & Norman (2010[Jayaratna, N. B. & Norman, R. E. (2010). Acta Cryst. E66, o3149.]); Fun & Kia (2008[Fun, H.-K. & Kia, R. (2008). Acta Cryst. E64, o1840-o1841.]); Warad et al. (2012[Warad, I., Alruwaili, A., Al-Resayes, S. I., Choudhary, M. I. & Yousuf, S. (2012). Acta Cryst. E68, o1786.]). For competition between cyclization and bisimine formation, see: Locke et al. (2009[Locke, J., Griffith, R., Bailey, T. & Crumbie, R. (2009). Tetrahedron, 65, 10685-10692.]). For the use of hexahydropyrimidines as polydentate ligands for the synthesis of transition metal coordination complexes, see: Schmidt et al. (2011[Schmidt, M., Wiedemann, D. & Grohmann, A. (2011). Inorg. Chim. Acta, 374, 514-520.]).

[Scheme 1]

Experimental

Crystal data
  • C14H16N4

  • Mr = 240.31

  • Monoclinic, P 21 /c

  • a = 14.2372 (14) Å

  • b = 8.0302 (8) Å

  • c = 11.3277 (9) Å

  • [beta] = 103.075 (8)°

  • V = 1261.5 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Agilent (2011). CrysAlis PRO. Agilent Technologies UK Ltd, Yarnton, Enngland.]) Tmin = 0.98, Tmax = 0.99

  • 4640 measured reflections

  • 2238 independent reflections

  • 1656 reflections with I > 2[sigma](I)

  • Rint = 0.023

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.108

  • S = 1.05

  • 2238 reflections

  • 171 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.14 e Å-3

  • [Delta][rho]min = -0.15 e Å-3

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)
Symmetry code: (i) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies UK Ltd, Yarnton, Enngland.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and ORTEP (Burnett & Johnson, 1996[Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NK2200 ).


Acknowledgements

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

References

Agilent (2011). CrysAlis PRO. Agilent Technologies UK Ltd, Yarnton, Enngland.
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.
Fun, H.-K. & Kia, R. (2008). Acta Cryst. E64, o1840-o1841.  [CSD] [CrossRef] [details]
Jayaratna, N. B. & Norman, R. E. (2010). Acta Cryst. E66, o3149.  [CSD] [CrossRef] [details]
Locke, J., Griffith, R., Bailey, T. & Crumbie, R. (2009). Tetrahedron, 65, 10685-10692.  [ISI] [CrossRef] [ChemPort]
Schmidt, M., Wiedemann, D. & Grohmann, A. (2011). Inorg. Chim. Acta, 374, 514-520.  [ISI] [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Song, X.-P., Li, G.-C., Wu, C.-Z. & Yang, F.-L. (2010). Acta Cryst. E66, o1083.  [CSD] [CrossRef] [details]
Warad, I., Alruwaili, A., Al-Resayes, S. I., Choudhary, M. I. & Yousuf, S. (2012). Acta Cryst. E68, o1786.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o569  [ doi:10.1107/S1600536813007459 ]

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