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Volume 68 
Part 11 
Page o3172  
November 2012  

Received 15 September 2012
Accepted 12 October 2012
Online 20 October 2012

Key indicators
Single-crystal X-ray study
T = 120 K
Mean [sigma](C-C) = 0.002 Å
R = 0.033
wR = 0.104
Data-to-parameter ratio = 14.0
Details
Open access

4,4'-Dimethyl-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 bInstitute of Physics ASCR, v.v.i., Na Slovance 2, 182 21 Praha 8, Czech Republic
Correspondence e-mail: ariverau@unal.edu.co

The imidazolidine ring in the title compound, C19H24N2O2, adopts a twist conformation and its mean plane (r.m.s. deviation = 0.19 Å) makes dihedral angles of 72.38 (9) and 71.64 (9)° with the two pendant aromatic rings. The dihedral angle between the phenyl rings is 55.94 (8)°. The molecular structure shows the presence of two intramolecular O-H...N hydrogen bonds between the phenolic hydroxyl groups and N atoms with graph-set motif S(6). In the crystal, C-H...O hydrogen bonds lead to the formation of chains along the b-axis direction.

Related literature

For the anti-inflammatory and analgesic properties of imidazolidines, see: Sharma & Khan (2001[Sharma, V. & Khan, M. S. Y. (2001). Eur. J. Med. Chem. 36, 651-658.]). 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.], 2012[Rivera, A., Nerio, L. S., Ríos-Motta, J., Fejfarová, K. & Dusek, M. (2012). Acta Cryst. E68, o170-o171.]). For the preparation 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 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 ring conformations, see Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). 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
  • C19H24N2O2

  • Mr = 312.4

  • Monoclinic, P 21 /n

  • a = 11.5029 (4) Å

  • b = 9.5001 (3) Å

  • c = 16.1874 (6) Å

  • [beta] = 107.078 (3)°

  • V = 1690.94 (10) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 0.63 mm-1

  • T = 120 K

  • 0.25 × 0.22 × 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 = 0.573, Tmax = 1

  • 12982 measured reflections

  • 3007 independent reflections

  • 2648 reflections with I > 3[sigma](I)

  • Rint = 0.021

Refinement
  • R[F2 > 2[sigma](F2)] = 0.033

  • wR(F2) = 0.104

  • S = 1.93

  • 3007 reflections

  • 215 parameters

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

  • [Delta][rho]max = 0.16 e Å-3

  • [Delta][rho]min = -0.14 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H2...N2 0.912 (17) 1.869 (16) 2.6893 (13) 148.6 (16)
O2-H1...N1 0.923 (17) 1.825 (15) 2.6807 (12) 153.0 (15)
C17-H1c17...O1i 0.96 2.48 3.4286 (14) 168.38
Symmetry code: (i) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z-{\script{1\over 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: LR2083 ).


Acknowledgements

We acknowledge the Dirección de Investigaciones, Sede Bogotá (DIB) de la Universidad Nacional de Colombia, for financial support of this work as well as the Praemium Academiae project of the Academy of Sciences of the Czech Republic. LSN thanks COLCIENCIAS 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.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
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] [ISI]
Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.  [ISI] [CrossRef] [ChemPort] [details]
Petrícek, V., Dusek, M. & Palatinus, L. (2006). JANA2006. Institute of Physics, Praha, Czech Republic.
Rivera, A., Gallo, G. I., Gayón, M. E. & Joseph-Nathan, P. (1993). Synth. Commun. 23, 2921-2929.  [CrossRef] [ChemPort] [ISI]
Rivera, A., Nerio, L. S., Ríos-Motta, J., Fejfarová, K. & Dusek, M. (2012). Acta Cryst. E68, o170-o171.  [CSD] [CrossRef] [details]
Rivera, A., Sadat-Bernal, J., Ríos-Motta, J., Pojarová, M. & Dusek, M. (2011). Acta Cryst. E67, o2581.  [CSD] [CrossRef] [details]
Sharma, V. & Khan, M. S. Y. (2001). Eur. J. Med. Chem. 36, 651-658.  [ISI] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2012). E68, o3172  [ doi:10.1107/S1600536812042808 ]

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