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Volume 69 
Part 8 
Pages o1295-o1296  
August 2013  

Received 11 July 2013
Accepted 14 July 2013
Online 20 July 2013

Key indicators
Single-crystal X-ray study
T = 120 K
Mean [sigma](C-C) = 0.003 Å
Disorder in main residue
R = 0.040
wR = 0.048
Data-to-parameter ratio = 12.7
Details
Open access

2,2'-{[2-(2-Hydroxyphenyl)-4-methylimidazolidine-1,3-diyl]bis(methylene)}diphenol

aDepartamento de Química, Facultad de Ciencias, Universidad Nacional de Colombia, Sede Bogotá, Cra 30 No. 45-03, Bogotá, Código Postal 111321, Colombia, and bInstitute of Physics, Academy of Sciences of the Czech Republic v.v.i., Na Slovance 2, 182 21 Praha 8, Czech Republic
Correspondence e-mail: ariverau@unal.edu.co

The asymmetric unit in the title compound, C24H26N2O3, comprises two independent molecules (A and B). In molecule A, the central 2-hydroxyphenyl ring is inclined to the mean plane of the major component of the imidazolidine ring by 84.52 (14)°, and by 68.08 (9) and 47.48 (9)° to the outer phenol rings. The later are inclined to one another by 66.76 (9)° and by 78.12 (14) and 80.20 (14)° to the imidazoline ring mean plane. In molecule B, the central 2-hydroxyphenyl ring is inclined to the mean plane of the imidazolidine ring by 73.64 (10)°, and by 75.60 (8) and 38.32 (9)° to the outer phenol rings. The later are inclined to one another by 69.47 (9)° and by 82.60 (10) and 64.26 (10)° to the imidazolidine ring mean plane. In each of the independent molecules, two intramolecular O-H...N hydrogen bond form S(6) ring motifs. In disordered molecule A, the O-H groups of the 2-hydroxybenzyl groups are also involved in intramolecular O-H...O hydrogen bonds, with the O atom of the hydroxyphenyl group acting as the acceptor. In the crystal, A molecules are linked by pairs of O-H...O hydrogen bonds forming inversion dimers. These dimers are linked to the B molecules via O-H...O hydrogen bonds forming double-layered slabs lying parallel to the bc plane.

Related literature

For related structures, see: Rivera et al. (2012[Rivera, A., Pacheco, D., Ríos-Motta, J., Fejfarová, K. & Dusek, M. (2012). Tetrahedron Lett. 53, 6132-6135.], 2013b[Rivera, A., Cárdenas, L., Ríos-Motta, J., Eigner, V. & Dusek, M. (2013b). Acta Cryst. E69, o1198.],c[Rivera, A., Cárdenas, L., Ríos-Motta, J., Kuceraková, M. & Dusek, M. (2013c). Acta Cryst. E69, o1221-o1222.]). For the synthesis of the title compound, see: Rivera et al. (2013a[Rivera, A., Cárdenas, L. & Ríos-Motta, J. (2013a). Curr. Org. Chem. In the press.]). For reference 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.]). For Cremer-Pople ring-puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C24H26N2O3

  • Mr = 390.47

  • Monoclinic, C 2/c

  • a = 24.2482 (10) Å

  • b = 9.8145 (3) Å

  • c = 35.1675 (15) Å

  • [beta] = 102.450 (4)°

  • V = 8172.5 (6) Å3

  • Z = 16

  • Cu K[alpha] radiation

  • [mu] = 0.67 mm-1

  • T = 120 K

  • 0.20 × 0.11 × 0.05 mm

Data collection
  • Agilent Xcalibur Gemini ultra diffractometer with Atlas detector

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.]) Tmin = 0.505, Tmax = 1.000

  • 15999 measured reflections

  • 7053 independent reflections

  • 5315 reflections with I > 3[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.048

  • S = 1.68

  • 7053 reflections

  • 556 parameters

  • 7 restraints

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

  • [Delta][rho]max = 0.31 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...N3 0.883 (14) 1.838 (16) 2.6344 (17) 148.9 (19)
O2-H2...N4 0.883 (15) 1.937 (16) 2.7360 (17) 149.7 (18)
O3-H3...N2 0.883 (16) 1.839 (17) 2.6680 (17) 155.5 (19)
O4-H4...N1 0.883 (19) 1.849 (19) 2.646 (2) 149.0 (14)
O1-H1...O5 0.883 (14) 2.472 (19) 3.0381 (18) 122.4 (16)
O4-H4...O5 0.883 (14) 2.523 (17) 3.1167 (15) 125.3 (15)
O5-H5...O1i 0.883 (14) 1.930 (15) 2.8108 (18) 174.9 (16)
O6-H6...O4ii 0.883 (16) 1.907 (14) 2.746 (2) 157.9 (18)
Symmetry codes: (i) -x+2, -y, -z; (ii) [x, -y, z+{\script{1\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2010[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, 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, Prague, 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: SJ5345 ).


Acknowledgements

The authors 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, Oxfordshire, 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, Prague, Czech Republic.
Rivera, A., Cárdenas, L. & Ríos-Motta, J. (2013a). Curr. Org. Chem. In the press.
Rivera, A., Cárdenas, L., Ríos-Motta, J., Eigner, V. & Dusek, M. (2013b). Acta Cryst. E69, o1198.  [CrossRef] [IUCr Journals]
Rivera, A., Cárdenas, L., Ríos-Motta, J., Kuceraková, M. & Dusek, M. (2013c). Acta Cryst. E69, o1221-o1222.  [CrossRef] [IUCr Journals]
Rivera, A., Pacheco, D., Ríos-Motta, J., Fejfarová, K. & Dusek, M. (2012). Tetrahedron Lett. 53, 6132-6135.  [Web of Science] [CSD] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o1295-o1296   [ doi:10.1107/S1600536813019417 ]

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