6H,13H-5,12:7,14-Dimethano­dinaphtho­[2,3-d:2,3-i][1,3,6,8]tetra­azecine

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

doi:10.1107/S1600536812010185

Volume 68
Part 4
Page o1061
April 2012

Received 11 January 2012
Accepted 7 March 2012
Online 14 March 2012

Key indicators
Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.002 Å
R = 0.027
wR = 0.077
Data-to-parameter ratio = 5.4
Details

6H,13H-5,12:7,14-Dimethanodinaphtho[2,3-d:2,3-i][1,3,6,8]tetraazecine

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

^aUniversidad Nacional de Colombia, Sede Bogotá, Facultad de Ciencias, Departamento de Química, Grupo de Investigación Síntesis de Heterociclos, Cra 30 No.45-03, Bogotá, Código Postal 111321, 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

In the title compound, C₂₄H₂₀N₄, obtained through the condensation of naphthalene-2,3-diamine with formaldehyde in methanol, the molecule is located on a special position of site symmetry -4. Due to symmetry considerations, the aromatic rings are strictly perpendicular to each other. In the crystal, molecules are linked by pairs of C-H [pi] interactions into columns along [110].

Related literature

For chemical background to the synthesis of the title compound, see: Volpp (1962). For related structures, see: Murray-Rust & Smith (1975); Rivera et al. (2009, 2011). For bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₂₄H₂₀N₄
M_r = 364.5
Tetragonal, $[I \overline 42m ]$
a = 7.1996 (2) Å
c = 17.4511 (5) Å
V = 904.56 (6) Å³
Z = 2
Cu K radiation
= 0.63 mm^-1
T = 120 K
0.45 × 0.22 × 0.15 mm

Data collection

Agilent Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010) T_min = 0.50, T_max = 0.90
4873 measured reflections
273 independent reflections
268 reflections with I > 3(I)
R_int = 0.025

Refinement

R[F² > 2(F²)] = 0.027
wR(F²) = 0.077
S = 1.85
273 reflections
51 parameters
Only H-atom coordinates refined
_max = 0.08 e Å^-3
_min = -0.15 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C2-C4/C2'-C4' and C4-C6/C4'-C6' rings, respectively.

D-HA	D-H	HA	DA	D-HA
C3-H3Cg2ⁱ	1.042 (18)	2.648 (14)	3.6921 (14)	178.2 (15)
C5-H5Cg1ⁱ	1.047 (18)	2.652 (14)	3.6979 (14)	178.0 (16)
Symmetry code: (i) $[-y+{\script{1\over 2}}, x-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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: BG2445 ).

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.
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
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.
Murray-Rust, P. & Smith, I. (1975). Acta Cryst. B31, 587-589.
Petrícek, V., Dusek, M. & Palatinus, L. (2006). JANA2006. Institute of Physics, Prague, Czech Republic.
Rivera, A., Maldonado, M., Ríos-Motta, J., Fejfarová, K. & Dusek, M. (2011). Acta Cryst. E67, o2395.
Rivera, A., Maldonado, M., Ríos-Motta, J., González-Salas, D. & Dacunha-Marinho, B. (2009). Acta Cryst. E65, o2553.
Volpp, G. (1962). Chem. Ber. 95, 1493-1494.

organic compounds