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Volume 70 
Part 1 
Page o5  
January 2014  

Received 11 November 2013
Accepted 19 November 2013
Online 4 December 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.020
wR = 0.049
Data-to-parameter ratio = 19.1
Details
Open access

Benzyl­tris­[2-(di­benzyl­amino)­eth­yl]ammonium iodide

aDepartment of Chemistry, 1253 University of Oregon, Eugene, Oregon 97403-1253, USA, and bCAMCOR, University of Oregon, 1443 E. 13th Avenue, Eugene, Oregon 97403, USA
Correspondence e-mail: dtyler@uoregon.edu

In the title quaternary ammonium salt, C55H61N4+·I-, all three N,N-di­benzyl­ethanamine, -(CH2)2N(CH2C6H5)2, groups have different conformations. The N-C-C-N torsion angles are significantly different [89.86 (13), 162.61 (10) and 175.70 (10)°] and the dihedral angles between the phenyl rings in these groups are different as well [58.21 (4), 43.73 (4) and 76.72 (5)°]. In the crystal, the I- anions fill empty spaces between the bulky cations. The cations and anions are linked by weak C-H...I inter­actions, forming a chain along [110].

Related literature

For related ligand structures, see: Farrell et al. (2003[Farrell, D., Gloe, K., Gloe, K., Goretzki, G., McKee, V., Nelson, J., Nieuwenhuyzen, M., Pal, I., Stephan, H. & Town, R. M. (2003). Dalton Trans. pp. 1961-1968.]). For the application of similar ligands coordinating to copper in the catalysis of atom-transfer radical polymerization or click reactions, see: Barré et al. (2004[Barré, G., Taton, D., Lastécouères, D. & Vincent, J.-M. (2004). J. Am. Chem. Soc. 126, 7764-7765.]); Candelon et al. (2008[Candelon, N., Lastécouères, D., Diallo, A. K., Ruiz Aranzaes, J., Astruc, D. & Vincent, J.-M. (2008). Chem. Commun. pp. 741-743.]); Liang et al. (2011[Liang, L., Ruiz, J. & Astruc, D. (2011). Adv. Synth. Catal. 353, 3434-3450.]); Brady & Tyler (2012[Brady, S. E. & Tyler, D. R. (2012). J. Inorg. Organomet. Polym. Mater. 23, 158-166.]).

[Scheme 1]

Experimental

Crystal data
  • C55H61N4+·I-

  • Mr = 904.98

  • Triclinic, [P \overline 1]

  • a = 11.1254 (10) Å

  • b = 14.3871 (13) Å

  • c = 15.9525 (15) Å

  • [alpha] = 94.491 (3)°

  • [beta] = 101.972 (3)°

  • [gamma] = 106.229 (3)°

  • V = 2372.9 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.72 mm-1

  • T = 100 K

  • 0.25 × 0.24 × 0.11 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.842, Tmax = 0.926

  • 53881 measured reflections

  • 10377 independent reflections

  • 9802 reflections with I > 2[sigma](I)

  • Rint = 0.030

Refinement
  • R[F2 > 2[sigma](F2)] = 0.020

  • wR(F2) = 0.049

  • S = 1.04

  • 10377 reflections

  • 542 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.38 e Å-3

  • [Delta][rho]min = -0.42 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C39-H39A...I1i 0.95 3.01 3.893 (2) 154
C49-H49B...I1ii 0.99 2.86 3.8187 (13) 162
Symmetry codes: (i) -x, -y, -z+1; (ii) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5322 ).


Acknowledgements

SEB would like to acknowledge the NSF Graduate STEM Fellows in K-12 Education (GK-12) program (DGE-0742540) for support. This work was also partially supported by NSF grant CHE-0809393.

References

Barré, G., Taton, D., Lastécouères, D. & Vincent, J.-M. (2004). J. Am. Chem. Soc. 126, 7764-7765.  [Web of Science] [PubMed]
Brady, S. E. & Tyler, D. R. (2012). J. Inorg. Organomet. Polym. Mater. 23, 158-166.  [CrossRef]
Bruker (2000). SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2008). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Candelon, N., Lastécouères, D., Diallo, A. K., Ruiz Aranzaes, J., Astruc, D. & Vincent, J.-M. (2008). Chem. Commun. pp. 741-743.  [CrossRef]
Farrell, D., Gloe, K., Gloe, K., Goretzki, G., McKee, V., Nelson, J., Nieuwenhuyzen, M., Pal, I., Stephan, H. & Town, R. M. (2003). Dalton Trans. pp. 1961-1968.  [CSD] [CrossRef]
Liang, L., Ruiz, J. & Astruc, D. (2011). Adv. Synth. Catal. 353, 3434-3450.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2014). E70, o5  [ doi:10.1107/S1600536813031607 ]

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