2-[(2-Hydr­oxy-2,2-diphenyl­ethyl)(meth­yl)amino]-N,N-dimethyl­ethanaminium bromide

Gessner, V.H.; Däschlein, C.; Strohmann, C.

doi:10.1107/S1600536809002414

Volume 65
Part 2
Page o383
February 2009

Received 19 December 2008
Accepted 19 January 2009
Online 23 January 2009

Key indicators
Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.004 Å
R = 0.037
wR = 0.099
Data-to-parameter ratio = 16.6
Details

2-[(2-Hydroxy-2,2-diphenylethyl)(methyl)amino]-N,N-dimethylethanaminium bromide

Viktoria H. Gessner,^a Christian Däschlein ^a and Carsten Strohmann ^a ^*

^aAnorganische Chemie, Technische Universität Dortmund, Otto-Hahn-Strasse 6, 44227 Dortmund, Germany
Correspondence e-mail: mail@carsten-strohmann.de

The title compound, C₁₉H₂₇N₂O⁺·Br^-, is the hydrobromide of the trapping product of lithiated N,N,N',N'-tetramethylethylenediamine (TMEDA) with benzophenone. Thereby, the N atom of the NMe₂ group is selectively protonated and the respective trapping product represents a potential tridentate ligand with one O and two N donor atoms. The H atoms at N (H2N) and O (H1O) are involved in hydrogen bonds with the Br^-. The molecular structure shows all donor atoms to be arranged on one side of the molecule, thus indicating a potential threefold coordination of a Lewis acid.

Related literature

For related literature on direct deprotonation of tertiary amines, see: Strohmann & Gessner (2007a,b,c, 2008a,b), Gessner & Strohmann (2008); Bojer et al. (2007); Karsch (1996); Strohmann et al. (2008); Köhler et al. (1987); Arnold et al. (2002).

Experimental

Crystal data

C₁₉H₂₇N₂O⁺·Br^-
M_r = 379.34
Orthorhombic, P b c a
a = 7.119 (2) Å
b = 15.515 (3) Å
c = 33.585 (7) Å
V = 3710 (1) Å³
Z = 8
Mo K radiation
= 2.22 mm^-1
T = 173 (2) K
0.4 × 0.2 × 0.2 mm

Data collection

Bruker APEX CCD diffractometer
Absorption correction: empirical (using intensity measurements) (SADABS; Bruker, 1999) T_min = 0.440, T_max = 0.635
78737 measured reflections
3640 independent reflections
3200 reflections with I > 2(I)
R_int = 0.064

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.099
S = 1.07
3640 reflections
219 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.49 e Å^-3
_min = -0.43 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2NBr	0.87 (4)	2.52 (4)	3.276 (3)	145 (4)
O-H1OBr	0.69 (3)	2.76 (3)	3.398 (2)	156 (3)

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS90 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IM2095 ).

Acknowledgements

The authors are grateful to the Deutsche Forschungsgemeinschaft and the Fonds der Chemischen Industrie for financial support and the award of a scholarship (VHG). CD thanks the Studienstiftung des Deutschen Volkes for a doctoral scholarship.

References

Arnold, J., Knapp, V., Schmidt, J. A. R. & Shafir, A. (2002). J. Chem. Soc. Dalton Trans. pp. 3273-3274.
Bojer, D., Kamps, I., Tian, X., Hepp, A., Pape, T., Fröhlich, R. & Mitzel, N. W. (2007). Angew. Chem. Int. Ed. 46, 4176-4178.
Bruker (1999). SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2001). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Gessner, V. H. & Strohmann, C. (2008). J. Am. Chem. Soc. 130, 14412-14413.
Karsch, H. H. (1996). Chem. Ber. 129, 483-484.
Köhler, F. H., Hertkorn, N. & Blümel, J. (1987). Chem. Ber. 120, 2081-2082.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Strohmann, C., Damme, A. & Gessner, V. (2008). Chem. Commun. pp. 3381-3383.
Strohmann, C. & Gessner, V. H. (2007a). J. Am. Chem. Soc. 129, 8952-8953.
Strohmann, C. & Gessner, V. H. (2007b). Angew. Chem. Int. Ed. 46, 4566-4569.
Strohmann, C. & Gessner, V. H. (2007c). Angew. Chem. Int. Ed. 46, 8281-8283.
Strohmann, C. & Gessner, V. H. (2008a). J. Am. Chem. Soc. 130, 11719-11725.
Strohmann, C. & Gessner, V. H. (2008b). Chem. Asian J. 3, 1929-1934.

organic compounds