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Volume 69 
Part 7 
Page o1166  
July 2013  

Received 18 June 2013
Accepted 20 June 2013
Online 29 June 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.010 Å
R = 0.119
wR = 0.324
Data-to-parameter ratio = 14.4
Details
Open access

4,4'-Di-tert-butyl-2,2'-[imidazolidine-1,3-diylbis(methylene)]diphenol

aUniversidad Nacional de Colombia, Sede Bogotá, Facultad de Ciencias, Departamento de Química, Cra 30 No. 45-03, Bogotá, Código Postal 111321, Colombia, and bInstitut für Anorganische Chemie, J. W. Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt/Main, Germany
Correspondence e-mail: ariverau@unal.edu.co

In the title compound, C25H36N2O2, the two tert-butyl-substituted benzene rings are inclined at an angle of 53.5 (3)° to one another. The imidazolidine ring has an envelope conformation with with one of the C atoms of the ethylene fragment as the flap. The structure displays two intramolecular O-H...N hydrogen bonds that generate S(6) ring motifs. The crystal studied was a non-merohedral twin with a fractional contribution of 0.281(6) for the minor domain.

Related literature

For related structures, see: Rivera et al. (2011[Rivera, A., Sadat-Bernal, J., Ríos-Motta, J., Pojarová, M. & Dusek, M. (2011). Acta Cryst. E67, o2581.], 2012a[Rivera, A., Nerio, L. S., Ríos-Motta, J., Kuceráková, M. & Dusek, M. (2012a). Acta Cryst. E68, o3043-o3044.],b[Rivera, A., Nerio, L. S., Ríos-Motta, J., Kuceraková, M. & Dusek, M. (2012b). Acta Cryst. E68, o3172.]); Rivera, Nerio, Ríos-Motta, Fejfarová et al. (2012[Rivera, A., Nerio, L. S., Ríos-Motta, J., Fejfarová, K. & Dusek, M. (2012). Acta Cryst. E68, o170-o171.]). For the use of the 2,2'-[imidazolidine-1,3-diylbis(methylene)]diphenol system as a ligand in the synthesis of a variety of coordination compounds, see: Kober et al. (2012[Kober, E., Nerkowski, T., Janas, Z. & Jerzykiewicz, L. B. (2012). Dalton Trans. 41, 5188-5192.]); Xu et al. (2007[Xu, X., Yao, Y., Zhang, Y. & Shen, Q. (2007). Inorg. Chem. 46, 3743-3751.]); Zhang et al. (2009[Zhang, Z., Xu, X., Li, W., Yao, Y., Zhang, Y., Shen, Q. & Luo, Y. (2009). Inorg. Chem. 48, 5715-5724.]). For the original synthesis of the title compound, see: Rivera et al. (1993[Rivera, A., Gallo, G. I., Gayón, M. E. & Joseph-Nathan, P. (1993). Synth. Commun. 23, 2921-2929.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C25H36N2O2

  • Mr = 396.56

  • Monoclinic, P 21 /c

  • a = 21.0879 (16) Å

  • b = 6.2110 (4) Å

  • c = 17.9086 (16) Å

  • [beta] = 109.168 (6)°

  • V = 2215.6 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 173 K

  • 0.24 × 0.22 × 0.19 mm

Data collection
  • Stoe IPDS II two-circle diffractometer

  • 22835 measured reflections

  • 3909 independent reflections

  • 3131 reflections with I > 2[sigma](I)

  • Rint = 0.101

Refinement
  • R[F2 > 2[sigma](F2)] = 0.119

  • wR(F2) = 0.324

  • S = 1.13

  • 3909 reflections

  • 272 parameters

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

  • [Delta][rho]max = 0.42 e Å-3

  • [Delta][rho]min = -0.39 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...N1 1.00 (10) 1.70 (10) 2.655 (7) 157 (8)
O2-H2...N2 0.95 (8) 1.83 (8) 2.656 (7) 144 (7)

Data collection: X-AREA (Stoe & Cie, 2001[Stoe & Cie (2001). X-AREA and XRED-32. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: XRED-32 (Stoe & Cie, 2001[Stoe & Cie (2001). X-AREA and XRED-32. Stoe & Cie, Darmstadt, Germany.]); 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: DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5337 ).


Acknowledgements

The authors acknowledge the Dirección de Investigaciones, Sede Bogotá (DIB) de la Universidad Nacional de Colombia, for financial support of this work. LSN thanks COLCIENCIAS for a fellowship.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [Web of Science]
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Kober, E., Nerkowski, T., Janas, Z. & Jerzykiewicz, L. B. (2012). Dalton Trans. 41, 5188-5192.  [CSD] [CrossRef] [ChemPort] [PubMed]
Rivera, A., Gallo, G. I., Gayón, M. E. & Joseph-Nathan, P. (1993). Synth. Commun. 23, 2921-2929.  [CrossRef] [ChemPort] [Web of Science]
Rivera, A., Nerio, L. S., Ríos-Motta, J., Fejfarová, K. & Dusek, M. (2012). Acta Cryst. E68, o170-o171.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Rivera, A., Nerio, L. S., Ríos-Motta, J., Kuceráková, M. & Dusek, M. (2012a). Acta Cryst. E68, o3043-o3044.  [CrossRef] [ChemPort] [IUCr Journals]
Rivera, A., Nerio, L. S., Ríos-Motta, J., Kuceraková, M. & Dusek, M. (2012b). Acta Cryst. E68, o3172.  [CrossRef] [IUCr Journals]
Rivera, A., Sadat-Bernal, J., Ríos-Motta, J., Pojarová, M. & Dusek, M. (2011). Acta Cryst. E67, o2581.  [CSD] [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Stoe & Cie (2001). X-AREA and XRED-32. Stoe & Cie, Darmstadt, Germany.
Xu, X., Yao, Y., Zhang, Y. & Shen, Q. (2007). Inorg. Chem. 46, 3743-3751.  [Web of Science] [CSD] [CrossRef] [PubMed] [ChemPort]
Zhang, Z., Xu, X., Li, W., Yao, Y., Zhang, Y., Shen, Q. & Luo, Y. (2009). Inorg. Chem. 48, 5715-5724.  [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o1166  [ doi:10.1107/S1600536813017157 ]

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