2,2′-(1,3-Diazinane-1,3-di­yl)diaceto­nitrile: a second monoclinic polymorph

Rivera, A.; Maldonado, M.; Ríos-Motta, J.; Fejfarová, K.; Dušek, M.

doi:10.1107/S1600536811038013

Volume 67
Part 10
Page o2734
October 2011

Received 15 August 2011
Accepted 16 September 2011
Online 30 September 2011

Key indicators
Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.003 Å
R = 0.039
wR = 0.093
Data-to-parameter ratio = 12.9
Details

2,2'-(1,3-Diazinane-1,3-diyl)diacetonitrile: a second monoclinic polymorph

Augusto Rivera,^a ^* Mauricio Maldonado,^a Jaime Ríos-Motta,^a Karla Fejfarová ^b and Michal Dusek ^b

^aDepartamento de Química, Universidad Nacional de Colombia, Ciudad Universitaria, Bogotá, Colombia, and ^bInstitute of Physics ASCR, v.v.i., Na Slovance 2, 182 21 Praha 8, Czech Republic
Correspondence e-mail: ariverau@unal.edu.co

A new monoclinic polymorph of the title compound, C₈H₁₂N₄, in the space group P2₁/n (Z = 4) is reported. The previously known form was also monoclinic, P2₁/c (Z = 4), but the unit-cell parameters and crystal packing were different [Shoja & Saba (1993). Acta Cryst. C49, 354-355]. The hexahydropyrimidine ring of the title compound adopts a chair conformation with a diequatorial substitution and with the CH₂-C [triple bond] N groups oriented nearly parallel and in the same direction [NC-CH₂CH₂-CN pseudo torsion angle = -6.27 (18)°]. In the crystal, intermolecular C-H N hydrogen bonds connects the molecules into a chain along the b axis.

Related literature

For the original monoclinic polymorph, see: Shoja & Saba (1993). For the synthesis of the title compound, see: Rivera et al. (2004); Katritzky et al. (1990). For the use of nitriles in synthesis, see: Prasad & Bhalla (2010).

Experimental

Crystal data

C₈H₁₂N₄
M_r = 164.2
Monoclinic, P 2₁ /n
a = 11.1300 (6) Å
b = 6.3501 (3) Å
c = 13.1373 (7) Å
= 102.066 (6)°
V = 907.99 (8) Å³
Z = 4
Cu K radiation
= 0.63 mm^-1
T = 120 K
0.16 × 0.09 × 0.01 mm

Data collection

Agilent Gemini Ultra diffractometer with an Atlas CCD detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010) T_min = 0.864, T_max = 1.000
2863 measured reflections
1404 independent reflections
929 reflections with I > 3(I)
R_int = 0.027

Refinement

R[F² > 2(F²)] = 0.039
wR(F²) = 0.093
S = 1.30
1404 reflections
109 parameters
H-atom parameters constrained
_max = 0.18 e Å^-3
_min = -0.18 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C7-H7BN4ⁱ	0.96	2.59	3.396 (3)	141
Symmetry code: (i) $[-x-{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: JANA2006 (Petrícek et al. 2006); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: JANA2006.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2401 ).

Acknowledgements

We acknowledge the Dirección de Investigaciones, Sede Bogotá (DIB) de la Universidad Nacional de Colombia, for financial support of this work, as well as the Institutional research plan No. AVOZ10100521 of the Institute of Physics and the Praemium Academiae project of the Academy of Sciences of the Czech Republic.

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact, Bonn, Germany.
Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.
Katritzky, A. R., Pilarski, B. & Urogdi, L. (1990). J. Chem. Soc. Perkin Trans. 1, pp. 541-547.
Petrícek, V., Dusek, M. & Palatinus, L. (2006). JANA2006. Institute of Physics, Praha, Czech Republic.
Prasad, S. & Bhalla, T. C. (2010). Biotechnol. Adv. 28, 725-741.
Rivera, A., Núñez, M. E., Maldonado, M. & Joseph-Nathan, P. (2004). Heterocycl. Commun. 10, 77-80.
Shoja, M. & Saba, S. (1993). Acta Cryst. C49, 354-355.

organic compounds