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Volume 69 
Part 7 
Pages o1057-o1058  
July 2013  

Received 23 May 2013
Accepted 31 May 2013
Online 8 June 2013

Key indicators
Single-crystal X-ray study
T = 120 K
Mean [sigma](C-C) = 0.003 Å
R = 0.031
wR = 0.080
Data-to-parameter ratio = 13.0
Details
Open access

meso-4,4'-Dimethoxy-2,2'-{[(3aR,7aS)-2,3,3a,4,5,6,7,7a-octahydro-1H-benzimidazole-1,3-diyl]bis(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 bInstitute of Physics ASCR, v.v.i., Na Slovance 2, 182 21 Praha 8, Czech Republic
Correspondence e-mail: ariverau@unal.edu.co

The title compound, C23H30N2O4, a di-Mannich base derived from 4-methoxyphenol and cis-1,2-diaminecyclohexane, has a perhydrobenzimidazolidine nucleus, in which the cyclohexane ring adopts a chair conformation and the heterocyclic ring has a half-chair conformation with a C-N-C-C torsion angles of -48.14 (15) and -14.57 (16)°. The mean plane of the heterocycle makes dihedral angles of 86.29 (6) and 78.92 (6)° with the pendant benzene rings. The molecular structure of the title compound shows the presence of two interactions between the N atoms of the imidazolidine ring and the hydroxyl groups through intramolecular O-H...N hydrogen bonds with graph-set motif S(6). The unobserved lone pairs of the N atoms are presumed to be disposed in a syn conformation, being only the second example of an exception to the typical `rabbit-ears' effect in 1,2-diamines.

Related literature

For related structures, see: Rivera et al. (2011[Rivera, A., Quiroga, D., Ríos-Motta, J., Fejfarová, K. & Dusek, M. (2011). Acta Cryst. E67, o2298-o2299.], 2013a[Rivera, A., Quiroga, D., Ríos-Motta, J., Kuceraková, M. & Dusek, M. (2013a). Acta Cryst. E69, o217.]). For the preparation of the title compound, see: Rivera et al. (2013b[Rivera, A., Quiroga, D., Ríos-Motta, J., Václav, E. & Dusek, M. (2013b). Chem. Cent. J. Accepted for publication.]). For standard bond lengths, see: Allen et al. (1987[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.]). For hydrogen-bond graph-set nomenclature, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For a discussion of the `rabbit-ear' effect in 1,2-diamines, see: Hutchins et al. (1968[Hutchins, R. O., Kopp, L. D. & Eliel, E. L. (1968). J. Am. Chem. Soc. 90, 7174-7175.]). For background to this work, see: Van den Enden & Geise (1981[Van den Enden, L. & Geise, H. J. (1981). J. Mol. Struct. 74, 309-320.]); Geise et al. (1971[Geise, H. J., Buys, H. R. & Mijlhoff, F. C. (1971). J. Mol. Struct. 9, 447-454.]). For the extinction correction, see: Becker & Coppens (1974[Becker, P. J. & Coppens, P. (1974). Acta Cryst. A30, 129-147.]).

[Scheme 1]

Experimental

Crystal data
  • C23H30N2O4

  • Mr = 398.5

  • Orthorhombic, P 21 21 21

  • a = 6.4135 (3) Å

  • b = 11.4099 (6) Å

  • c = 27.8249 (14) Å

  • V = 2036.15 (18) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 0.72 mm-1

  • T = 120 K

  • 0.21 × 0.13 × 0.13 mm

Data collection
  • Agilent Xcalibur (Atlas, Gemini ultra) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.341, Tmax = 1

  • 5920 measured reflections

  • 3491 independent reflections

  • 3103 reflections with I > 3[sigma](I)

  • Rint = 0.023

Refinement
  • R[F2 > 2[sigma](F2)] = 0.031

  • wR(F2) = 0.080

  • S = 1.13

  • 3491 reflections

  • 269 parameters

  • 1 restraint

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

  • [Delta][rho]max = 0.11 e Å-3

  • [Delta][rho]min = -0.09 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O3-H1o3...N2 0.93 (2) 1.78 (2) 2.6443 (19) 154.4 (19)
O1-H1o1...N1 0.93 (2) 1.83 (2) 2.6638 (19) 148.8 (18)

Data collection: CrysAlis PRO (Agilent, 2010[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis 2007[Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.]); program(s) used to refine structure: JANA2006 (Petrícek et al., 2006[Petrícek, V., Dusek, M. & Palatinus, L. (2006). JANA2006. Institute of Physics, Praha, Czech Republic.]); molecular graphics: DIAMOND (Brandenburg & Putz, 2005[Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact, Bonn, Germany.]); software used to prepare material for publication: JANA2006.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5324 ).


Acknowledgements

We acknowledge the Dirección de Investigaciones, Sede Bogotá (DIB) de laUniversidad Nacional de Colombia, for financial support of this work and the Praemium Academiae project of the Academy of Sciences of the Czech Republic. DQ acknowledges the Vicerrectoría Académica de la Universidad Nacional de Colombia for a fellowship.

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.
Becker, P. J. & Coppens, P. (1974). Acta Cryst. A30, 129-147.  [CrossRef] [IUCr Journals]
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. & Putz, H. (2005). DIAMOND. Crystal Impact, Bonn, Germany.
Geise, H. J., Buys, H. R. & Mijlhoff, F. C. (1971). J. Mol. Struct. 9, 447-454.  [CrossRef] [ChemPort] [Web of Science]
Hutchins, R. O., Kopp, L. D. & Eliel, E. L. (1968). J. Am. Chem. Soc. 90, 7174-7175.  [CrossRef] [ChemPort] [Web of Science]
Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Petrícek, V., Dusek, M. & Palatinus, L. (2006). JANA2006. Institute of Physics, Praha, Czech Republic.
Rivera, A., Quiroga, D., Ríos-Motta, J., Fejfarová, K. & Dusek, M. (2011). Acta Cryst. E67, o2298-o2299.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Rivera, A., Quiroga, D., Ríos-Motta, J., Kuceraková, M. & Dusek, M. (2013a). Acta Cryst. E69, o217.  [CSD] [CrossRef] [IUCr Journals]
Rivera, A., Quiroga, D., Ríos-Motta, J., Václav, E. & Dusek, M. (2013b). Chem. Cent. J. Accepted for publication.
Van den Enden, L. & Geise, H. J. (1981). J. Mol. Struct. 74, 309-320.  [CrossRef] [ChemPort] [Web of Science]


Acta Cryst (2013). E69, o1057-o1058   [ doi:10.1107/S1600536813015092 ]

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