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Volume 69 
Part 8 
Page o1198  
August 2013  

Received 27 June 2013
Accepted 28 June 2013
Online 3 July 2013

Key indicators
Single-crystal X-ray study
T = 120 K
Mean [sigma](C-C) = 0.002 Å
Disorder in main residue
R = 0.042
wR = 0.113
Data-to-parameter ratio = 12.6
Details
Open access

2,2'-[(4-Methyl-2-phenylimidazolidine-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,bDepartment of Solid State Chemistry, Institute of Chemical Technology, Technická 5, 166 28 Prague, Czech Republic, and cInstitute of Physics AS CR, v.v.i., Na Slovance 2, 182 21 Prague 8, Czech Republic
Correspondence e-mail: ariverau@unal.edu.co

The methyl-substituted imidazolidine ring of the title compound, C24H26N2O2, adopts an envelope conformation with the N atom adjacent to the methylene group as the flap. The methyl-ethylene fragment in this ring is disordered over two positions with an occupancy ratio of 0.899 (4):0.101 (4). The hydroxybenzyl groups are inclined at 71.57 (15) and 69.97 (19)° to the mean plane of major disorder component of the heterocyclic ring with an interplanar angle between the two hydroxybenzyl groups of 66.00 (5)°. The phenyl substituent approaches a nearly perpendicular orientation relative to the mean plane of the imidazolidine ring, making a dihedral angle of 75.60 (12)°. This conformation is stabilized by two intramolecular O-H...N bonds, which generate S(6) ring motifs.

Related literature

For related structures, see: Rivera et al. (2012a[Rivera, A., Nerio, L. S., Ríos-Motta, J., Fejfarová, K. & Dusek, M. (2012a). Acta Cryst. E68, o170-o171.],b[Rivera, A., Pacheco, D., Ríos-Motta, J., Fejfarová, K. & Dusek, M. (2012b). Tetrahedron Lett. 53, 6132-6135.]). For the synthesis of the precursor, 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 puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For hydrogen-bond graph-set 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
  • C24H26N2O2

  • Mr = 374.5

  • Monoclinic, P 21 /c

  • a = 16.8974 (8) Å

  • b = 9.4893 (5) Å

  • c = 12.5287 (6) Å

  • [beta] = 92.928 (4)°

  • V = 2006.29 (17) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 0.62 mm-1

  • T = 120 K

  • 0.35 × 0.25 × 0.09 mm

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

  • Absorption correction: analytical (CrysAlis PRO; Agilent, 2010[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.886, Tmax = 0.952

  • 8259 measured reflections

  • 3491 independent reflections

  • 2704 reflections with I > 3[sigma](I)

  • Rint = 0.03

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.113

  • S = 1.51

  • 3491 reflections

  • 276 parameters

  • 5 restraints

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

  • [Delta][rho]max = 0.25 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1o1...N9 0.98 (2) 1.88 (2) 2.7569 (18) 147.7 (19)
O19-H1o19...N11 1.00 (2) 1.79 (2) 2.709 (2) 152 (2)

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: SJ5339 ).


Acknowledgements

We acknowledge the Dirección de Investigaciones, Sede Bogotá (DIB), and the Institutional research plan No. AVOZ10100521 of the Institute of Physics and the Praemium Academiae project of the Academy of Sciences (ASCR).

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.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [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., Cárdenas, L. & Ríos-Motta, J. (2013). Curr. Org. Chem. Accepted.
Rivera, A., Nerio, L. S., Ríos-Motta, J., Fejfarová, K. & Dusek, M. (2012a). Acta Cryst. E68, o170-o171.  [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, o1198  [ doi:10.1107/S1600536813017893 ]

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