[2,6-Bis(dimethyl­amino­meth­yl)phen­yl]selenium bromide monohydrate

Varga, R.A.; Kulcsar, M.; Silvestru, A.

doi:10.1107/S1600536810008019

Volume 66
Part 4
Page o771
April 2010

Received 4 February 2010
Accepted 2 March 2010
Online 6 March 2010

Key indicators
Single-crystal X-ray study
T = 297 K
Mean (C-C) = 0.005 Å
R = 0.039
wR = 0.086
Data-to-parameter ratio = 18.5
Details

[2,6-Bis(dimethylaminomethyl)phenyl]selenium bromide monohydrate

Richard A. Varga,^a ^* Monica Kulcsar ^b and Anca Silvestru ^a

^aFaculty of Chemistry and Chemical Engineering, Babes-Bolyai University, Arany Janos Str. no. 11, RO-400028, Cluj Napoca, Romania, and ^bDepartamento de Química Inorgánica, Instituto de Ciencia de, Materiales de Aragón, Universidad de Zaragoza-CSIC, E-50009 Zaragoza, Spain
Correspondence e-mail: richy@chem.ubbcluj.ro

In the title hydrated molecular salt, C₁₂H₁₉N₂Se⁺·Br^-·H₂O, the two independent bromide anions lie on a twofold rotation axis. Strong intramolecular N [rightwards arrow] Se interactions [2.185 (3) and 2.181 (3) Å] are established by both N atoms of the organic group in the cation, in trans positions to each other, with an N-Se-N angle of 161.6 (1)°, resulting in a T-shaped (C,N,N')Se core. In the crystal, dimeric associations are formed by BrSe [3.662 (2) Å] and BrH interactions [2.56 (6) and 2.63 (7) Å] involving two bromide anions, two cations and two water molecules.

Related literature

For related selenium and tellurium compounds, see: Drake et al. (2001a,b); Deleanu et al. (2002); Kulcsar et al. (2005, 2007); Beleaga et al. (2009); Fujihara et al. (1995). For van der Waals radii, see: Emsley (1994).

Experimental

Crystal data

C₁₂H₁₉N₂Se⁺·Br^-·H₂O
M_r = 368.18
Monoclinic, C 2/c
a = 15.1494 (14) Å
b = 11.3182 (10) Å
c = 18.8083 (17) Å
= 110.475 (2)°
V = 3021.2 (5) Å³
Z = 8
Mo K radiation
= 5.12 mm^-1
T = 297 K
0.31 × 0.29 × 0.09 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000) T_min = 0.300, T_max = 0.656
11856 measured reflections
3093 independent reflections
2696 reflections with I > 2/s(I)
R_int = 0.050

Refinement

R[F² > 2(F²)] = 0.039
wR(F²) = 0.086
S = 1.09
3093 reflections
167 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.49 e Å^-3
_min = -0.53 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1Br2	0.78 (6)	2.56 (6)	3.340 (5)	175 (5)
O1-H2Br1	0.78 (6)	2.63 (7)	3.406 (5)	176 (7)

Data collection: SMART (Bruker, 2000); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND 3 (Brandenburg & Putz, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: DN2538 ).

Acknowledgements

This work was supported by the Romanian Ministery of Education and Research (PNII Program, grant 2404/2008). We also thank the National Center for X-ray Diffraction, Cluj-Napoca, for the structure determination.

References

Beleaga, A., Kulcsar, M., Deleanu, C., Nicolescu, A., Silvestru, C. & Silvestru, A. (2009). J. Organomet. Chem. 694, 1308-1316.
Brandenburg, K. & Putz, H. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2000). SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2001). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.
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Kulcsar, M., Silvestru, A., Silvestru, C., Drake, J. E., Macdonald, C. L. B., Hursthouse, M. B. & Leight, M. E. (2005). J. Organomet. Chem. 690, 3217-3228.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2010). publCIF. In preparation.

organic compounds