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

Rivera, A.; Sadat-Bernal, J.; Ríos-Motta, J.; Pojarová, M.; Dušek, M.

doi:10.1107/S1600536811035677

Volume 67
Part 10
Page o2581
October 2011

Received 25 August 2011
Accepted 1 September 2011
Online 14 September 2011

Key indicators
Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.002 Å
R = 0.035
wR = 0.101
Data-to-parameter ratio = 14.4
Details

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

Augusto Rivera,^a ^* John Sadat-Bernal,^a Jaime Ríos-Motta,^a Michaela Pojarová ^b and Michal Dusek ^b

^aDepartamento de Química, Universidad Nacional de Colombia, Ciudad Universitaria, Bogotá, Colombia, and ^bInstitute of Physics, AS CR, 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, C₁₇H₁₈Cl₂N₂O₂, adopts a twist conformation. The observed conformation is stabilized by two intramolecular O-HN hydrogen bonds, with both N atoms acting as hydrogen-bond acceptors. The phenyl substituents are aligned at 70.0 (1) and 76.6 (1)° with respect to the best plane through the five atoms of the imidazolidine ring. Weak intermolecular C-HO interactions stabilize the crystal packing.

Related literature

For the preparation of the title compound, see: Rivera et al. (1993). For synthetic applications of these di-Mannich bases, see: Rivera & Quevedo (2004); Rivera et al. (2004). For a closely related structure, see: Rivera et al. (2010). For puckering parameters, see: Cremer & Pople (1975). For applications of tetrahydrosalens and heterocalixarenes in medicine and metal-complex catalysis, see: Balsells & Walsh (2000); Weber et al. (1996).

Experimental

Crystal data

C₁₇H₁₈Cl₂N₂O₂
M_r = 353.23
Monoclinic, P 2₁ /n
a = 10.8640 (2) Å
b = 9.6125 (2) Å
c = 16.7242 (4) Å
= 106.608 (2)°
V = 1673.65 (6) Å³
Z = 4
Cu K radiation
= 3.58 mm^-1
T = 120 K
0.42 × 0.37 × 0.25 mm

Data collection

Oxford Diffraction Xcalibur Atlas Gemini ultra diffractometer
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis PRO CCD. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.669, T_max = 0.777
19547 measured reflections
2994 independent reflections
2772 reflections with I > 2(I)'
R_int = 0.040

Refinement

R[F² > 2(F²)] = 0.035
wR(F²) = 0.101
S = 1.04
2994 reflections
208 parameters
H-atom parameters constrained
_max = 0.29 e Å^-3
_min = -0.30 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1O1N1	0.97	1.77	2.6524 (17)	149
O2-H1O2N2	0.96	1.77	2.6515 (17)	150
C4-H4BO2ⁱ	0.97	2.52	3.466 (2)	163
C9-H9O2ⁱⁱ	0.93	2.47	3.395 (2)	172
C11-H11BO1ⁱⁱⁱ	0.97	2.58	3.482 (2)	154
Symmetry codes: (i) -x+1, -y, -z+1; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis PRO CCD. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: publCIF (Westrip, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5631 ).

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 Institutional research plan No. AVOZ10100521 of the Institute of Physics and the project Praemium Academiae of the Academy of Science of the Czech Republic. JSB acknowledges the Vicerrectoría Académica de la Universidad Nacional de Colombia for a fellowship.

References

Balsells, J. & Walsh, P. J. (2000). J. Am. Chem. Soc. 122, 1802-1803.
Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact, Bonn, Germany.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Oxford Diffraction (2010). CrysAlis PRO and CrysAlis PRO CCD. Oxford Diffraction Ltd, Yarnton, England.
Rivera, A., Gallo, G. I., Gayón, M. E. & Joseph-Nathan, P. (1993). Synth. Commun. 23, 2921-2929.
Rivera, A. & Quevedo, R. (2004). Tetrahedron Lett. 45, 8335-8338.
Rivera, A., Quevedo, R., Navarro, M. A. & Maldonado, M. (2004). Synth. Commun. 34, 2479-2485.
Rivera, A., Quiroga, D., Ríos-Motta, J., Dusek, M. & Fejfarová, K. (2010). Acta Cryst. E66, o2643.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Weber, E., Trepte, J., Piel, M., Czugler, M., Kravtsov, V. Ch., Somonov, Y. A., Lipkowski, J. & Ganin, E. V. (1996). J. Chem. Soc. Perkin Trans 2, pp. 2359-2366.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds