[Journal logo]

Volume 69 
Part 7 
Pages o1133-o1134  
July 2013  

Received 12 June 2013
Accepted 17 June 2013
Online 22 June 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.005 Å
R = 0.065
wR = 0.142
Data-to-parameter ratio = 12.5
Details
Open access

Naphthalene-1,8-diamine-2-(pyrimidin-2-yl)-1H-perimidine (2/1)

aDipartimento di Scienze Chimiche, Università degli Studi di Napoli 'Federico II', Complesso di Monte S. Angelo, Via Cinthia, 80126 Napoli, Italy, and bDipartimento di Agraria, Università degli Studi di Napoli 'Federico II', Via Università 100, 80055 Portici, Italy
Correspondence e-mail: angela.tuzi@unina.it

In the title adduct, C15H10N4·2C10H10N2, the pyrimidine ring is nearly co-planar with the heteroatomic perimidine ring, as indicated dihedral angle between their mean planes of 3.21 (11)°. The diaminonaphthalene molecules are slightly twisted [dihedral angles = 4.2 (2) and 3.0 (2)°] because of the steric encumbrance of NH2 groups. The perimidine and diaminonaphthalene molecules are linked by N-H...N hydrogen bonds, forming an R44(12) graph-set motif across an inversion center. In the crystal, alternating layers of the perimidine and diaminonaphthalene molecules are formed along [100]. In the perimidine layer, molecules are [pi]-[pi] stacked along the c-axis direction with an interplane separation of approximately 3.4 Å.

Related literature

For the coordination properties of perimidines, see: Morita et al. (2003[Morita, Y., Suzuki, S., Fukui, K., Nakazawa, S., Sato, K., Shiomi, D., Takui, T. & Nakasuji, K. (2003). Polyhedron, 39, 2215-2218.]); Cucciolito et al. (2013[Cucciolito, M. E., Panunzi, B., Ruffo, F. & Tuzi, A. (2013). Tetrahedron Lett. 54, 1503-1506.]). For structural data on perimidines, see: Foces-Foces et al. (1993[Foces-Foces, C., Llamas-Saiz, A. L., Claramunt, R. M., Sanz, D., Dotor, J. & Elguero, J. (1993). J. Crystallogr. Spectrosc. Res. 23, 305-312.]); Llamas-Saiz et al. (1995[Llamas-Saiz, A. L., Foces-Foces, C., Sanz, D., Claramunt, R. M., Dotor, J., Elguero, J., Catalàn, J. & Carlos del Valle, J. (1995). J. Chem. Soc. Perkin Trans. 2, pp. 1389-1398.]); Filatova et al. (2000[Filatova, E. A., Borovlev, I. V., Pozharskii, A. F., Starikova, Z. A. & Vistorobskii, N. V. (2000). Mendeleev Commun. pp. 178-180.]); Murata et al. (2006[Murata, T., Morita, Y., Fukui, K., Tamaki, K., Yamochi, H., Saito, G. & Nakasuji, K. (2006). Bull. Chem. Soc. Jpn, 79, 894-913.]); Smellie et al. (2011[Smellie, I. A. S., Fromm, A. & Paton, R. M. (2011). Carbohydr. Res. 346, 43-49.]). For structural data on naphthalene-1,8-diamine, see: Llamas-Saiz et al. (1991[Llamas-Saiz, A. L., Foces-Foces, C., Molina, P., Alajarin, M., Vidal, A., Claramunt, R. M. & Elguero, J. (1991). J. Chem. Soc. Perkin Trans. 2, pp. 1025-1031.]); Basaran et al. (1993[Basaran, R., Dou, S. & Weiss, A. (1993). Struct. Chem. 4, 219-233.]); Batsanov et al. (2001[Batsanov, A. S., Collings, J. C., Howard, J. A. K. & Marder, T. B. (2001). Acta Cryst. E57, o950-o952.]). For N-rich aromatic heterocycles in organic electronics and photonics, see: Goswami et al. (2010[Goswami, S., Sen, D. & Das, N. K. (2010). Org. Lett. 12, 856-859.]); Carella et al. (2012[Carella, A., Borbone, F., Roviello, A., Roviello, G., Tuzi, A., Kravinsky, A., Shikler, R., Cantele, G. & Ninno, G. (2012). Dyes Pigments, 95, 116-125.]); Centore et al. (2012[Centore, R., Ricciotti, L., Carella, A., Roviello, A., Causà, M., Barra, M., Ciccullo, F. & Cassinese, A. (2012). Org. Electron. 132083-2093.]). For a general survey of hydrogen bonding in crystals, see: Desiraju & Steiner (1999[Desiraju, G. R. & Steiner, T. (1999). In The Weak Hydrogen Bond. New York: Oxford University Press Inc.]); Steiner (2002[Steiner, T. (2002). Angew. Chem. Int. Ed. 41, 48-76.]). For hydrogen-bonding patterns in nitrogen-containing heterocycles, see: Centore et al. (2013a[Centore, R., Piccialli, V. & Tuzi, A. (2013a). Acta Cryst. E69, o667-o668.],b[Centore, R., Piccialli, V. & Tuzi, A. (2013b). Acta Cryst. E69, o802-o803.]).

[Scheme 1]

Experimental

Crystal data
  • C15H10N4·2C10H10N2

  • Mr = 562.67

  • Monoclinic, P 21 /c

  • a = 17.083 (2) Å

  • b = 12.139 (3) Å

  • c = 13.597 (2) Å

  • [beta] = 90.76 (1)°

  • V = 2819.4 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 173 K

  • 0.50 × 0.45 × 0.10 mm

Data collection
  • Bruker-Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.960, Tmax = 0.992

  • 22722 measured reflections

  • 5184 independent reflections

  • 2799 reflections with I > 2[sigma](I)

  • Rint = 0.080

Refinement
  • R[F2 > 2[sigma](F2)] = 0.065

  • wR(F2) = 0.142

  • S = 1.06

  • 5184 reflections

  • 415 parameters

  • 2 restraints

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

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...N2Ai 0.86 (3) 2.30 (3) 3.077 (4) 151 (2)
N1A-H1C...N2ii 0.87 (3) 2.42 (3) 3.153 (4) 142 (3)
N2A-H2C...N2 0.92 (3) 2.27 (3) 3.092 (4) 149 (3)
N2A-H2D...N1A 0.87 (3) 2.27 (3) 2.753 (5) 115 (2)
N1B-H1F...N2B 0.98 (4) 2.12 (3) 2.710 (5) 117 (2)
Symmetry codes: (i) -x, -y, -z+1; (ii) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: COLLECT (Nonius, 1999[Nonius (1999). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DIRAX/LSQ (Duisenberg et al., 2000[Duisenberg, A. J. M., Hooft, R. W. W., Schreurs, A. M. M. & Kroon, J. (2000). J. Appl. Cryst. 33, 893-898.]); data reduction: EVALCCD (Duisenberg et al., 2003[Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003). J. Appl. Cryst. 36, 220-229.]); program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GO2093 ).


Acknowledgements

The authors thank the Centro Interdipartimentale di Metodologie Chimico-Fisiche, Università degli Studi di Napoli "Federico II" for the X-ray facilities.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Basaran, R., Dou, S. & Weiss, A. (1993). Struct. Chem. 4, 219-233.  [CrossRef] [ChemPort] [Web of Science]
Batsanov, A. S., Collings, J. C., Howard, J. A. K. & Marder, T. B. (2001). Acta Cryst. E57, o950-o952.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Carella, A., Borbone, F., Roviello, A., Roviello, G., Tuzi, A., Kravinsky, A., Shikler, R., Cantele, G. & Ninno, G. (2012). Dyes Pigments, 95, 116-125.  [CSD] [CrossRef] [ChemPort]
Centore, R., Piccialli, V. & Tuzi, A. (2013a). Acta Cryst. E69, o667-o668.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Centore, R., Piccialli, V. & Tuzi, A. (2013b). Acta Cryst. E69, o802-o803.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Centore, R., Ricciotti, L., Carella, A., Roviello, A., Causà, M., Barra, M., Ciccullo, F. & Cassinese, A. (2012). Org. Electron. 132083-2093.
Cucciolito, M. E., Panunzi, B., Ruffo, F. & Tuzi, A. (2013). Tetrahedron Lett. 54, 1503-1506.
Desiraju, G. R. & Steiner, T. (1999). In The Weak Hydrogen Bond. New York: Oxford University Press Inc.
Duisenberg, A. J. M., Hooft, R. W. W., Schreurs, A. M. M. & Kroon, J. (2000). J. Appl. Cryst. 33, 893-898.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003). J. Appl. Cryst. 36, 220-229.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Filatova, E. A., Borovlev, I. V., Pozharskii, A. F., Starikova, Z. A. & Vistorobskii, N. V. (2000). Mendeleev Commun. pp. 178-180.  [CSD] [CrossRef]
Foces-Foces, C., Llamas-Saiz, A. L., Claramunt, R. M., Sanz, D., Dotor, J. & Elguero, J. (1993). J. Crystallogr. Spectrosc. Res. 23, 305-312.  [ChemPort]
Goswami, S., Sen, D. & Das, N. K. (2010). Org. Lett. 12, 856-859.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Llamas-Saiz, A. L., Foces-Foces, C., Molina, P., Alajarin, M., Vidal, A., Claramunt, R. M. & Elguero, J. (1991). J. Chem. Soc. Perkin Trans. 2, pp. 1025-1031.
Llamas-Saiz, A. L., Foces-Foces, C., Sanz, D., Claramunt, R. M., Dotor, J., Elguero, J., Catalàn, J. & Carlos del Valle, J. (1995). J. Chem. Soc. Perkin Trans. 2, pp. 1389-1398.
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Morita, Y., Suzuki, S., Fukui, K., Nakazawa, S., Sato, K., Shiomi, D., Takui, T. & Nakasuji, K. (2003). Polyhedron, 39, 2215-2218.  [Web of Science] [CrossRef]
Murata, T., Morita, Y., Fukui, K., Tamaki, K., Yamochi, H., Saito, G. & Nakasuji, K. (2006). Bull. Chem. Soc. Jpn, 79, 894-913.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Nonius (1999). COLLECT. Nonius BV, Delft, The Netherlands.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Smellie, I. A. S., Fromm, A. & Paton, R. M. (2011). Carbohydr. Res. 346, 43-49.  [Web of Science] [CSD] [CrossRef] [ChemPort] [PubMed]
Steiner, T. (2002). Angew. Chem. Int. Ed. 41, 48-76.  [Web of Science] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o1133-o1134   [ doi:10.1107/S1600536813016796 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.