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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 [sigma](C-C) = 0.003 Å
Disorder in main residue
R = 0.043
wR = 0.144
Data-to-parameter ratio = 14.1
Details
Open access

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

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-H...Cl 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[Xu, X., Yao, Y., Zhang, Y. & Shen, Q. (2007). Inorg. Chem. 46, 3743-3751.]). For related structures, see: Yang et al. (2009[Yang, S.-P., Han, L.-J., Wen, A.-P. & Wang, D.-Q. (2009). Acta Cryst. E65, o3049.]); Xia et al. (2007[Xia, H.-T., Liu, Y.-F., Wang, D.-Q. & Li, B. (2007). Acta Cryst. E63, o3666.]). For standard bond lengths, 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 ring conformations, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C24H25ClN2

  • Mr = 376.9

  • Monoclinic, P 21 /c

  • a = 7.1858 (1) Å

  • b = 9.8577 (2) Å

  • c = 29.3310 (5) Å

  • [beta] = 96.8591 (15)°

  • V = 2062.80 (6) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 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[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.62, Tmax = 0.751

  • 39415 measured reflections

  • 3665 independent reflections

  • 3464 reflections with I > 3[sigma](I)

  • Rint = 0.029

Refinement
  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.144

  • S = 2.91

  • 3665 reflections

  • 260 parameters

  • 4 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]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-H...A D-H H...A D...A D-H...A
C9-H1C9...Cl24 0.96 2.58 3.1596 (16) 119
C21-H1c21...Cg2i 0.96 2.87 3.6324 (19) 137
C11-H2c11...Cg2ii 0.96 2.82 3.6192 (19) 142
C4-H1c4...Cg3iii 0.96 2.79 3.695 (2) 157
C26-H1c26...Cg1iii 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[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, 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, Praha, 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: 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.  [CrossRef] [ChemPort] [ISI]
Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.  [ISI] [CrossRef] [ChemPort] [details]
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.  [CrossRef] [details]
Xu, X., Yao, Y., Zhang, Y. & Shen, Q. (2007). Inorg. Chem. 46, 3743-3751.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Yang, S.-P., Han, L.-J., Wen, A.-P. & Wang, D.-Q. (2009). Acta Cryst. E65, o3049.  [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o3427-o3428   [ doi:10.1107/S1600536812047575 ]

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