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Volume 66 
Part 8 
Pages o1958-o1959  
August 2010  

Received 8 June 2010
Accepted 30 June 2010
Online 10 July 2010

Key indicators
Single-crystal X-ray study
T = 300 K
Mean [sigma](C-C) = 0.004 Å
R = 0.056
wR = 0.157
Data-to-parameter ratio = 13.5
Details
Open access

5,11-Diisopropyl-2,8-dimethyl-1H,7H-diimidazo[c,h][1,6]diazecine dihydrate

aUniversidad de Guanajuato, División de Ciencias e Ingeniería, Departamento de Ingeniería Física, Lomas del Bosque No. 103, Col. Lomas del Campestre, 37150 Leon, Gto., Mexico,bUniversidad de Guanajuato, División de Ciencias Naturales y Exactas, Departamento de Química, Noria Alta s/n, 36050 Guanajuato, Gto., Mexico, and cDEP Facultad de Ciencias Químicas, UANL, Guerrero y Progreso S/N, Col. Treviño, 64570 Monterrey, N.L., Mexico
Correspondence e-mail: mendozag@quijote.ugto.mx

Crystals of the title compound, C18H30N6·2H2O, are composed of units of diimidazo[c,h][1,6]diazecine and two water molecules. The asymmetric unit contains one half-molecule of diazecine and one uncoordinated water molecule in a general position. The complete ten-membered heterocycle is generated by an inversion center.The organic residue and water molecules form a two-dimensional hydrogen-bonded network. The 1,6-diazecine ring shows a chair conformation, with angles and distances in normal ranges.

Related literature

For background to imidazoles, see: Bouwman et al. (1990[Bouwman, E., Driessen, W. L. & Reedijk, J. (1990). Coord. Chem. Rev. 104, 143-172.]). For the Mannich reaction, see: Stocker et al. (1970[Stocker, F. B., Kurtz, J. L., Byron, L. G. & Forsyth, D. A. (1970). J. Org. Chem. 35, 883-887.]). The reaction of formaldehyde, or other aldehydes, with different substrates and conditions has been widely used in organic synthesis, see: Teo et al. (1993[Teo, S.-B., Ng, C.-H. & Tiekink, E. R. T. (1993). J. Coord. Chem. 29, 57-63.]); Berndt (1970[Berndt, D. C. (1970). J. Org. Chem. 35, 1129-1131.]); Geue et al. (1994[Geue, R. J., Höhn, A., Ralph, S. F., Sargeson, A. M. & Willis, A. C. (1994). J. Chem. Soc. Chem. Commun. pp. 1513-1515.]); Karunakaran & Kandaswamy (1994[Karunakaran, S. & Kandaswamy, M. (1994). J. Chem. Soc. Dalton Trans. pp. 1595-1598.]); Baumann et al. (1984[Baumann, G. C., Summers, M. F., Hutchinson, J. P., Zubieta, J. & Marzilli, L. G. (1984). Inorg. Chem. 23, 3104-3108.]); Stocker et al. (1970[Stocker, F. B., Kurtz, J. L., Byron, L. G. & Forsyth, D. A. (1970). J. Org. Chem. 35, 883-887.]); Mendoza-Díaz et al. (1996[Mendoza-Díaz, G., Driessen, W. L. & Reedijk, J. (1996). Acta Cryst. C52, 960-962.]). For a similar structure, see: Mendoza-Díaz et al. (2002[Mendoza-Díaz, G., Driessen, W. L., Reedijk, J., Gorter, S., Gasque, L. & Thomson, K. R. (2002). Inorg. Chim. Acta, 339, 51-59.]). For the structures of copper complexes with different diazecine derivatives, see: Gasque, Mijangos & Ortiz-Frade (2005[Gasque, L., Mijangos, E. & Ortiz-Frade, L. (2005). Acta Cryst. E61, m673-m676.]); Gasque, Olguín & Bernès (2005[Gasque, L., Olguín, J. & Bernès, S. (2005). Acta Cryst. E61, m274-m276.]); Luna-Ramírez et al. (2008[Luna-Ramírez, K. S., Bernès, S. & Gasque, L. (2008). Acta Cryst. E64, m1135-m1136.]).

[Scheme 1]

Experimental

Crystal data
  • C18H30N6·2H2O

  • Mr = 366.51

  • Orthorhombic, P b c n

  • a = 12.571 (3) Å

  • b = 14.665 (3) Å

  • c = 10.877 (4) Å

  • V = 2005.3 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 300 K

  • 0.6 × 0.2 × 0.2 mm

Data collection
  • Siemens P4 diffractometer

  • 2495 measured reflections

  • 1768 independent reflections

  • 1126 reflections with I > 2[sigma](I)

  • Rint = 0.022

  • 3 standard reflections every 97 reflections intensity decay: 1%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.056

  • wR(F2) = 0.157

  • S = 1.72

  • 1768 reflections

  • 131 parameters

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

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O1ii 0.92 (2) 1.94 (2) 2.815 (3) 159 (2)
O1-H11...N3iii 0.99 (3) 1.91 (3) 2.890 (3) 169 (3)
O1-H12...N7iv 0.94 (3) 2.07 (3) 2.943 (2) 155 (3)
Symmetry codes: (ii) [-x+{\script{3\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (iii) [x, -y+1, z+{\script{1\over 2}}]; (iv) [-x+{\script{3\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: XSCANS (Siemens, 1996[Siemens (1996). XSCANS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: XSCANS; data reduction: XSCANS; 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: 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.]), PLUTON (Spek, 1992[Spek, A. L. (1992). PLUTON92. Utrecht University, The Netherlands.], 1993[Spek, A. L. (1993). PLUTON93. Utrecht University, The Netherlands.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); ; software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PB2033 ).


Acknowledgements

The authors are grateful to Dirección de Investigación y Posgrado de la Universidad de Guanajuato for financial support.

References

Baumann, G. C., Summers, M. F., Hutchinson, J. P., Zubieta, J. & Marzilli, L. G. (1984). Inorg. Chem. 23, 3104-3108.  [CrossRef] [ChemPort] [ISI]
Berndt, D. C. (1970). J. Org. Chem. 35, 1129-1131.  [CrossRef] [ChemPort]
Bouwman, E., Driessen, W. L. & Reedijk, J. (1990). Coord. Chem. Rev. 104, 143-172.  [CrossRef] [ChemPort] [ISI]
Gasque, L., Mijangos, E. & Ortiz-Frade, L. (2005). Acta Cryst. E61, m673-m676.  [CSD] [CrossRef] [details]
Gasque, L., Olguín, J. & Bernès, S. (2005). Acta Cryst. E61, m274-m276.  [CrossRef] [details]
Geue, R. J., Höhn, A., Ralph, S. F., Sargeson, A. M. & Willis, A. C. (1994). J. Chem. Soc. Chem. Commun. pp. 1513-1515.  [CrossRef] [ISI]
Karunakaran, S. & Kandaswamy, M. (1994). J. Chem. Soc. Dalton Trans. pp. 1595-1598.  [CrossRef]
Luna-Ramírez, K. S., Bernès, S. & Gasque, L. (2008). Acta Cryst. E64, m1135-m1136.  [CSD] [CrossRef] [details]
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.  [ISI] [CrossRef] [ChemPort] [details]
Mendoza-Díaz, G., Driessen, W. L. & Reedijk, J. (1996). Acta Cryst. C52, 960-962.  [CrossRef] [details]
Mendoza-Díaz, G., Driessen, W. L., Reedijk, J., Gorter, S., Gasque, L. & Thomson, K. R. (2002). Inorg. Chim. Acta, 339, 51-59.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Siemens (1996). XSCANS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
Spek, A. L. (1992). PLUTON92. Utrecht University, The Netherlands.
Spek, A. L. (1993). PLUTON93. Utrecht University, The Netherlands.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Stocker, F. B., Kurtz, J. L., Byron, L. G. & Forsyth, D. A. (1970). J. Org. Chem. 35, 883-887.  [CrossRef] [ChemPort]
Teo, S.-B., Ng, C.-H. & Tiekink, E. R. T. (1993). J. Coord. Chem. 29, 57-63.  [CrossRef] [ChemPort] [ISI]


Acta Cryst (2010). E66, o1958-o1959   [ doi:10.1107/S1600536810025808 ]

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