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Volume 69 
Part 7 
Page o1059  
July 2013  

Received 28 May 2013
Accepted 1 June 2013
Online 8 June 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.003 Å
R = 0.034
wR = 0.090
Data-to-parameter ratio = 16.8
Details
Open access

4,4'-Dimethyl-2,2'-{[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,bUniversidad Nacional de Colombia, Sede Manizales, Colombia, and cInstitut für Anorganische Chemie, J. W. Goethe-Universität Frankfurt, Max-von-Laue-Str. 7, 60438 Frankfurt/Main, Germany
Correspondence e-mail: ariverau@unal.edu.co

The asymmetric unit of the title compound, C23H30N2O2, contains one half-molecule, with a twofold axis splitting the molecule in two identical halves. The structure of the racemic mixture has been reported previously [Rivera et al. (2009[Rivera, A., Quiroga, D., Rios-Motta, J., Carda, J. & Peris, G. (2009). J. Chem. Crystallogr. 39, 827-830.]) J. Chem. Crystallogr. 39, 827-830] but the enantiomer reported here crystallized in the orthorhombic space group P21212 (Z = 2), whereas the racemate occurs in the triclinic space group P-1 (Z = 2). The observed molecular conformation is stabilized by two intramolecular O-H...N hydrogen bonds, which generate rings with graph-set motif S(6). In the crystal, molecules are linked via non-classical C-H...O interactions, which stack the molecules along the b axis.

Related literature

For the structure of the original racemate, see: Rivera et al. (2009[Rivera, A., Quiroga, D., Rios-Motta, J., Carda, J. & Peris, G. (2009). J. Chem. Crystallogr. 39, 827-830.]). For the use of 1,3-diazaheterocyclic-bridged bis(phenols) in coordination chemistry, 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.]). For the synthesis of the precursor, (2R,7R)- 1,8,10,12-tetraazatetracyclo[8.3.118,12.02,7]pentadecane, see: Rivera et al. (2012[Rivera, A., Quiroga, D., Jiménez-Cruz, L., Fejfarová, K. & Dusek, M. (2012). Tetrahedron Lett. 53, 345-348.]). For bond-length data, 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 graph-set analysis, 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
  • C23H30N2O2

  • Mr = 366.49

  • Orthorhombic, P 21 21 2

  • a = 18.5417 (9) Å

  • b = 6.0597 (4) Å

  • c = 8.9415 (5) Å

  • V = 1004.64 (10) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 173 K

  • 0.31 × 0.27 × 0.12 mm

Data collection
  • STOE IPDS II two-circle-diffractometer

  • Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001[Stoe & Cie (2001). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]) Tmin = 0.976, Tmax = 0.991

  • 12723 measured reflections

  • 2168 independent reflections

  • 2058 reflections with I > 2[sigma](I)

  • Rint = 0.053

Refinement
  • R[F2 > 2[sigma](F2)] = 0.034

  • wR(F2) = 0.090

  • S = 1.04

  • 2168 reflections

  • 129 parameters

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

  • [Delta][rho]max = 0.14 e Å-3

  • [Delta][rho]min = -0.13 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...N1 1.03 (4) 1.73 (4) 2.667 (2) 150 (3)
C4-H4...O1i 0.99 2.63 3.3749 (13) 133
C5-H5B...O1ii 0.99 2.63 3.522 (2) 150
Symmetry codes: (i) -x+1, -y+1, z; (ii) x, y-1, z.

Data collection: X-AREA (Stoe & Cie, 2001[Stoe & Cie (2001). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2001[Stoe & Cie (2001). X-AREA and X-RED32. 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: SHELXL2012 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL2012.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5327 ).


Acknowledgements

We acknowledge the Dirección de Investigaciones, Sede Bogotá (DIB) y Sede Manizales (DIMA) de la Universidad Nacional de Colombia, for financial support of this work

References

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.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [Web of Science]
Kober, E., Nerkowski, T., Janas, Z. & Jerzykiewicz, L. B. (2012). Dalton Trans. 41, 5188-5192.  [CSD] [CrossRef] [ChemPort] [PubMed]
Rivera, A., Quiroga, D., Jiménez-Cruz, L., Fejfarová, K. & Dusek, M. (2012). Tetrahedron Lett. 53, 345-348.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Rivera, A., Quiroga, D., Rios-Motta, J., Carda, J. & Peris, G. (2009). J. Chem. Crystallogr. 39, 827-830.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Stoe & Cie (2001). X-AREA and X-RED32. 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]


Acta Cryst (2013). E69, o1059  [ doi:10.1107/S1600536813015237 ]

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