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Volume 69 
Part 8 
Pages o1221-o1222  
August 2013  

Received 28 May 2013
Accepted 28 June 2013
Online 10 July 2013

Key indicators
Single-crystal X-ray study
T = 120 K
Mean [sigma](C-C) = 0.004 Å
R = 0.057
wR = 0.081
Data-to-parameter ratio = 13.9
Details
Open access

2,2'-{[2-(2-Chlorophenyl)-4-methylimidazolidine-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

In the title compound, C24H25ClN2O2, the 2-hydroxybenzyl substituents and the 2-chlorophenyl group occupy the sterically preferred equatorial positions, whereas the methyl group occupies the axial position. The imidazolidine ring adopts an envelope conformation with one of the N atoms adjacent to the methylene group as the flap. The chlorophenyl substituent approaches a nearly perpendicular orientation relative to the mean plane of the imidazolidine ring, making a dihedral angle of 73.44 (12)° and the Cl atom is almost coplanar with the C atom bearing the chlorophenyl substituent [Cl-C-C-C torsion angle = 1.1 (3)°]. The hydroxybenzyl groups make dihedral angles of 71.23 (15) and 69.13 (19)° with the mean plane of the heterocyclic ring. The dihedral angle between the two hydroxybenzyl groups is 69.61 (12)°. The molecular structure features two intramolecular O-H...N hydrogen bonds with graph-set motif S(6) between the phenolic hydroxyl groups and N atoms.

Related literature

For related structures, see: Rivera et al. (2012a[Rivera, A., Cardenas, L., Ríos-Motta, J., Eigner, V. & Dusek, M. (2012a). Acta Cryst. E68, o3427-o3428.],b[Rivera, A., Pacheco, D., Ríos-Motta, J., Fejfarová, K. & Dusek, M. (2012b). Tetrahedron Lett. 53, 6132-6135.]). For the synthesis of the title compound, see: Rivera et al. (2013[Rivera, A., Cárdenas, L. & Ríos-Motta, J. (2013). Curr. Org. Chem. Accepted.]). 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 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.]).

[Scheme 1]

Experimental

Crystal data
  • C24H25ClN2O2

  • Mr = 408.9

  • Monoclinic, P 21 /c

  • a = 7.0281 (2) Å

  • b = 9.7903 (3) Å

  • c = 30.3813 (6) Å

  • [beta] = 94.168 (2)°

  • V = 2084.92 (10) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.21 mm-1

  • T = 120 K

  • 0.24 × 0.15 × 0.08 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 = 0.392, Tmax = 1

  • 25057 measured reflections

  • 3732 independent reflections

  • 3164 reflections with I > 3[sigma](I)

  • Rint = 0.034

Refinement
  • R[F2 > 2[sigma](F2)] = 0.057

  • wR(F2) = 0.081

  • S = 2.66

  • 3732 reflections

  • 268 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 1.29 e Å-3

  • [Delta][rho]min = -0.33 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...N2 1.01 (3) 1.79 (3) 2.721 (3) 152 (3)
O2-H2...N1 1.01 (3) 1.79 (3) 2.723 (3) 152 (3)

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: BX2443 ).


Acknowledgements

We acknowledge the Dirección de Investigaciones, Sede Bogotá (DIB), and the Praemium Academiae project of the Academy of Sciences of the Czech Republic.

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.
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.
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., Cárdenas, L. & Ríos-Motta, J. (2013). Curr. Org. Chem. Accepted.
Rivera, A., Cardenas, L., Ríos-Motta, J., Eigner, V. & Dusek, M. (2012a). Acta Cryst. E68, o3427-o3428.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Rivera, A., Pacheco, D., Ríos-Motta, J., Fejfarová, K. & Dusek, M. (2012b). Tetrahedron Lett. 53, 6132-6135.  [Web of Science] [CSD] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o1221-o1222   [ doi:10.1107/S1600536813017923 ]

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