2,8,9-Tris(2-methyl­prop­yl)-2,5,8,9-tetra­aza-1λ5-phosphatricyclo­[3.3.3.01,5]undecan-5-ium chloride dihydrate

Lee, J.; Kim, Y.

doi:10.1107/S1600536812045618

Volume 68
Part 12
Page o3317
December 2012

Received 23 October 2012
Accepted 5 November 2012
Online 10 November 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.006 Å
Disorder in main residue
R = 0.068
wR = 0.212
Data-to-parameter ratio = 17.4
Details

2,8,9-Tris(2-methylpropyl)-2,5,8,9-tetraaza-1⁵-phosphatricyclo[3.3.3.0^1,5]undecan-5-ium chloride dihydrate

Junseong Lee ^a and Youngjo Kim ^b ^*

^aDepartment of Chemistry, Chonnam National University, Gwangju 500-757, Republic of Korea, and ^bDepartment of Chemistry, Chungbuk National University, Cheongju, Chungbuk 361-763, Republic of Korea
Correspondence e-mail: ykim@chungbuk.ac.kr

The asymmetric unit of the title hydrated salt, C₁₈H₄₀N₄P⁺·Cl^-·2H₂O, consists of two ionic molecules and four water molecules. The molecular geometry around the pentacoordinate P atom is trigonal-bipyramidal, with a H atom and an apical N atom in axial positions and three N atoms with isobutyl substituents in equatorial positions. The Cl^- ions and water molecules are connected via O-HCl hydrogen bonds, forming chains along [100]. The ethylene bridging groups are disordered with refined site-occupancy ratios of 0.578 (9):0.422 (9).

Related literature

For background to the applications of related compounds, see: Raders & Verkade (2010); Tang et al. (1993); Verkade & Kisang (2003); Zhou et al. (2011). For similar structure types, see: Kingston & Verkade (2005); Kisanga & Verkade (2001); Liu et al. (1999, 2000); Mohan et al. (1996); Thirupathi et al. (2003); Wroblewski et al. (1995).

Experimental

Crystal data

C₁₈H₄₀N₄P⁺·Cl^-·2H₂O
M_r = 414.99
Triclinic, $[P \overline 1]$
a = 10.0945 (19) Å
b = 15.759 (3) Å
c = 16.122 (3) Å
= 106.720 (8)°
= 92.259 (8)°
= 90.616 (8)°
V = 2453.6 (8) Å³
Z = 4
Mo K radiation
= 0.24 mm^-1
T = 296 K
0.20 × 0.15 × 0.14 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004) T_min = 0.954, T_max = 0.967
35181 measured reflections
9856 independent reflections
5364 reflections with I > 2(I)
R_int = 0.063

Refinement

R[F² > 2(F²)] = 0.068
wR(F²) = 0.212
S = 1.01
9856 reflections
568 parameters
18 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.39 e Å^-3
_min = -0.31 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H101Cl2ⁱ	0.84 (6)	2.61 (6)	3.426 (6)	164 (5)
O1-H102Cl2ⁱⁱ	0.93 (9)	2.32 (9)	3.208 (6)	159 (7)
O2-H103Cl2ⁱⁱⁱ	0.85 (7)	2.60 (7)	3.412 (7)	161 (5)
O2-H104Cl2ⁱⁱ	0.81 (8)	2.38 (9)	3.188 (6)	177 (8)
O3-H105Cl1ⁱⁱⁱ	0.86 (5)	2.45 (5)	3.263 (6)	159 (4)
O3-H106Cl1^iv	0.85 (4)	2.45 (4)	3.286 (6)	165 (4)
O4-H108Cl1ⁱⁱⁱ	0.73 (5)	2.56 (5)	3.286 (6)	175 (4)
Symmetry codes: (i) -x, -y+1, -z+1; (ii) x, y-1, z; (iii) -x+1, -y+1, -z+1; (iv) x-1, y, z.

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FF2086 ).

Acknowledgements

This work was supported by a research grant from Chungbuk Nation University in 2012.

References

Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Kingston, J. V. & Verkade, J. G. (2005). Inorg. Chem. Commun. 8, 643-646.
Kisanga, P. B. & Verkade, J. G. (2001). Tetrahedron, 57, 467-475.
Liu, X., Bai, Y. & Verkade, J. G. (1999). J. Organomet. Chem. 582, 16-24.
Liu, X., Ilankumaran, P., Guzei, I. A. & Verkade, J. G. (2000). J. Org. Chem. 65, 701-706.
Mohan, T., Arumugam, S., Wang, T., Jacobson, R. A. & Verkade, J. G. (1996). Heteroatom Chem. 7, 455-460.
Raders, M. R. & Verkade, J. G. (2010). J. Org. Chem. 75, 5308-5311.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Tang, J.-S., Dopke, J. & Verkade, J. G. (1993). J. Am. Chem. Soc. 115, 5015-5020.
Thirupathi, N., Liu, X. & Verkade, J. G. (2003). Inorg. Chem. 42, 389-397.
Verkade, J. G. & Kisanga, P. (2003). Tetrahedron, 59, 7819-7858.
Wroblewski, A., Pinkas, J. & Verkade, J. G. (1995). Main Group Chem. 1, 69-79.
Zhou, Y., Armstrong, D. W., Zhang, Y. & Verkade, J. G. (2011). Tetrahedron Lett. 52, 1545-1548.

organic compounds

2,8,9-Tris(2-methylpropyl)-2,5,8,9-tetraaza-15-phosphatricyclo[3.3.3.01,5]undecan-5-ium chloride dihydrate