4,4′-Dimethyl-2,2′-[imidazolidine-1,3-diylbis(methyl­ene)]diphenol

Rivera, A.; Nerio, L.S.; Ríos-Motta, J.; Kučeraková, M.; Dušek, M.

doi:10.1107/S1600536812042808

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 (C-C) = 0.002 Å
R = 0.033
wR = 0.104
Data-to-parameter ratio = 14.0
Details

4,4'-Dimethyl-2,2'-[imidazolidine-1,3-diylbis(methylene)]diphenol

Augusto Rivera,^a ^* Luz Stella Nerio,^a Jaime Ríos-Motta,^a Monika Kuceraková ^b and Michal Dusek ^b

^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-HN hydrogen bonds between the phenolic hydroxyl groups and N atoms with graph-set motif S(6). In the crystal, C-HO 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). For related structures, see: Rivera et al. (2011, 2012). For the preparation of the title compound, see: Rivera et al. (1993). For standard bond lengths, see: Allen et al. (1987). For ring conformations, see Cremer & Pople (1975). For hydrogen-bond graph-set nomenclature, see: Bernstein et al. (1995).

Experimental

Crystal data

C₁₉H₂₄N₂O₂
M_r = 312.4
Monoclinic, P 2₁ /n
a = 11.5029 (4) Å
b = 9.5001 (3) Å
c = 16.1874 (6) Å
= 107.078 (3)°
V = 1690.94 (10) Å³
Z = 4
Cu K radiation
= 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) T_min = 0.573, T_max = 1
12982 measured reflections
3007 independent reflections
2648 reflections with I > 3(I)
R_int = 0.021

Refinement

R[F² > 2(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
_max = 0.16 e Å^-3
_min = -0.14 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H2N2	0.912 (17)	1.869 (16)	2.6893 (13)	148.6 (16)
O2-H1N1	0.923 (17)	1.825 (15)	2.6807 (12)	153.0 (15)
C17-H1c17O1ⁱ	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); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: Superflip (Palatinus & Chapuis 2007); program(s) used to refine structure: JANA2006 (Petrícek et al., 2006); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); 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.
Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact, Bonn, Germany.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.
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.
Rivera, A., Nerio, L. S., Ríos-Motta, J., Fejfarová, K. & Dusek, M. (2012). Acta Cryst. E68, o170-o171.
Rivera, A., Sadat-Bernal, J., Ríos-Motta, J., Pojarová, M. & Dusek, M. (2011). Acta Cryst. E67, o2581.
Sharma, V. & Khan, M. S. Y. (2001). Eur. J. Med. Chem. 36, 651-658.

organic compounds