2,2′-[Imidazolidine-1,3-diylbis(methyl­ene)]diphenol

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

doi:10.1107/S1600536811053748

Volume 68
Part 1
Pages o170-o171
January 2012

Received 12 December 2011
Accepted 13 December 2011
Online 17 December 2011

Key indicators
Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.002 Å
R = 0.032
wR = 0.102
Data-to-parameter ratio = 13.2
Details

2,2'-[Imidazolidine-1,3-diylbis(methylene)]diphenol

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

^aDepartamento de Química, Universidad Nacional de Colombia, Ciudad Universitaria, Bogotá, 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

In the title molecule, C₁₇H₂₀N₂O₂, the imidazolidine ring adopts a twist conformation. The mean plane through the five atoms of the imidazolidine ring makes dihedral angles of 70.18 (4) and 74.14 (4)° with the planes of the two aromatic rings. The dihedral angle between the benzene rings is 53.11 (5)°. Both phenol -OH groups form intramolecular hydrogen bonds to the N atoms, with graph-set motif S(6). In the crystal, pairs of O-HO hydrogen bonds link the molecules into dimers with R₄⁴(18) ring motifs. The crystal packing is further stabilized by C-HO and weak C-H [pi] interactions.

Related literature

For a related structure, see: Rivera et al. (2011). For the preparation of the title compound, see: Rivera et al. (1993). For ring conformations, see Cremer & Pople (1975). For hydrogen-bond graph-set nomenclature, see: Bernstein et al. (1995). For details of hydrogen bonding in Mannich bases, see: Koll et al. (2006); Filarowski et al. (1997).

Experimental

Crystal data

C₁₇H₂₀N₂O₂
M_r = 284.4
Monoclinic, P 2₁ /n
a = 9.6541 (6) Å
b = 9.5198 (11) Å
c = 16.0007 (19) Å
= 97.321 (7)°
V = 1458.6 (3) Å³
Z = 4
Cu K radiation
= 0.68 mm^-1
T = 120 K
0.56 × 0.46 × 0.35 mm

Data collection

Agilent Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010) T_min = 0.684, T_max = 1
16045 measured reflections
2592 independent reflections
2323 reflections with I > 3(I)
R_int = 0.029

Refinement

R[F² > 2(F²)] = 0.032
wR(F²) = 0.102
S = 1.84
2592 reflections
197 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.18 e Å^-3
_min = -0.16 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C12-C17 benzene rings.

D-HA	D-H	HA	DA	D-HA
O1-H1oN1	0.88 (1)	1.83 (1)	2.6394 (13)	152 (2)
O2-H2oN2	0.88 (1)	1.84 (1)	2.6557 (13)	154 (2)
O1-H1oO1ⁱ	0.88 (1)	2.60 (2)	3.0232 (12)	111 (1)
C11-H11aO1ⁱ	0.96	2.58	3.4961 (15)	159
C14-H14O1ⁱⁱ	0.96	2.50	3.4561 (15)	172
C6-H6Cg3ⁱⁱⁱ	0.96	2.97	3.7868 (14)	143
C10-H10bCg3ⁱⁱ	0.96	2.83	3.6718 (13)	148
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2002 (Burla et al., 2003); 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: BT5752 ).

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 Praemium Academiae project of the Academy of Sciences of the Czech Republic.

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.
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.
Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Filarowski, A., Szemik-Hojniak, A., Glowiak, T. & Koll, A. (1997). J. Mol. Struct. 404, 67-74.
Koll, A., Karpfen, A. & Wolschann, P. (2006). J. Mol. Struct. 790, 55-64.
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., Sadat-Bernal, J., Ríos-Motta, J., Pojarová, M. & Dusek, M. (2011). Acta Cryst. E67, o2581.

organic compounds