1,3-Dibenzyl-2-(2-chloro­phen­yl)-4-methyl­imidazolidine

Rivera, A.; Cardenas, L.; Ríos-Motta, J.; Eigner, V.; Dušek, M.

doi:10.1107/S1600536812047575

Volume 68
Part 12
Pages o3427-o3428
December 2012

Received 8 November 2012
Accepted 19 November 2012
Online 24 November 2012

Key indicators
Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.003 Å
Disorder in main residue
R = 0.043
wR = 0.144
Data-to-parameter ratio = 14.1
Details

1,3-Dibenzyl-2-(2-chlorophenyl)-4-methylimidazolidine

Augusto Rivera,^a ^* Lorena Cardenas,^a Jaime Ríos-Motta,^a Václav Eigner ^b,^c and Michal Dusek ^c

^aUniversidad Nacional de Colombia, Sede Bogotá, Facultad de Ciencias, Departamento de Química, Cra 30 No. 45-03, Bogotá, Código Postal 111321, Colombia,^bDepartment of Solid State Chemistry, Institute of Chemical Technology, Technická 5, 166 28 Prague, Czech Republic, and ^cInstitute of Physics AS CR, v.v.i., Na Slovance 2, 182 21 Prague 8, Czech Republic
Correspondence e-mail: ariverau@unal.edu.co

In the title compound, C₂₄H₂₅ClN₂, the methine, methylene and methyl C atoms of the methyl-substituted imidazolidine ring are disordered over two sets of sites with a refined occupancy ratio of 0.834 (4):0.166 (4). Each disordered ring assumes an envelope conformation with an N atom as the flap. The pendant benzyl rings are oriented equatorially with respect to the imidazolidine ring. The chlorophenyl ring is inclined to the mean plane of the four planar atoms of the major component of the imidazolidine ring by 76.27 (12)°. The dihedral angles between the chlorophenyl ring and the two benzyl rings are 55.31 (9) and 57.50 (8)°; the dihedral angle between these latter rings is 71.59 (9)°. In the crystal, molecules are linked by C-HCl interactions and a number of weak C-H [pi] interactions, involving all three aromatic rings, forming a three-dimensional structure.

Related literature

For uses of imidazolidine-bridged bis(phenol) derivatives in coordination chemistry, see: Xu et al. (2007). For related structures, see: Yang et al. (2009); Xia et al. (2007). For standard bond lengths, see: Allen et al. (1987). For ring conformations, see: Cremer & Pople (1975).

Experimental

Crystal data

C₂₄H₂₅ClN₂
M_r = 376.9
Monoclinic, P 2₁ /c
a = 7.1858 (1) Å
b = 9.8577 (2) Å
c = 29.3310 (5) Å
= 96.8591 (15)°
V = 2062.80 (6) Å³
Z = 4
Cu K radiation
= 1.70 mm^-1
T = 120 K
0.44 × 0.32 × 0.21 mm

Data collection

Agilent Xcalibur (Atlas, Gemini ultra) diffractometer
Absorption correction: analytical (CrysAlis PRO; Agilent, 2010) T_min = 0.62, T_max = 0.751
39415 measured reflections
3665 independent reflections
3464 reflections with I > 3(I)
R_int = 0.029

Refinement

R[F² > 2(F²)] = 0.043
wR(F²) = 0.144
S = 2.91
3665 reflections
260 parameters
4 restraints
H-atom parameters constrained
_max = 0.24 e Å^-3
_min = -0.35 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C1-C6, C12-C17 and C18-C23 rings, respectively.

D-HA	D-H	HA	DA	D-HA
C9-H1C9Cl24	0.96	2.58	3.1596 (16)	119
C21-H1c21Cg2ⁱ	0.96	2.87	3.6324 (19)	137
C11-H2c11Cg2ⁱⁱ	0.96	2.82	3.6192 (19)	142
C4-H1c4Cg3ⁱⁱⁱ	0.96	2.79	3.695 (2)	157
C26-H1c26Cg1ⁱⁱⁱ	0.96	2.91	3.688 (2)	139
Symmetry codes: (i) x, y-1, z; (ii) -x+1, -y, -z; (iii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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: SU2527 ).

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. VE and MD acknowledge the suport provided by the project Praemium Academiae of the Academy of Sciences (ASCR), Czech Republic.

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.
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.
Xia, H.-T., Liu, Y.-F., Wang, D.-Q. & Li, B. (2007). Acta Cryst. E63, o3666.
Xu, X., Yao, Y., Zhang, Y. & Shen, Q. (2007). Inorg. Chem. 46, 3743-3751.
Yang, S.-P., Han, L.-J., Wen, A.-P. & Wang, D.-Q. (2009). Acta Cryst. E65, o3049.

organic compounds