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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 [sigma](C-C) = 0.006 Å
Disorder in main residue
R = 0.068
wR = 0.212
Data-to-parameter ratio = 17.4
Details
Open access

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

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-H...Cl 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[Raders, M. R. & Verkade, J. G. (2010). J. Org. Chem. 75, 5308-5311.]); Tang et al. (1993[Tang, J.-S., Dopke, J. & Verkade, J. G. (1993). J. Am. Chem. Soc. 115, 5015-5020.]); Verkade & Kisang (2003[Verkade, J. G. & Kisanga, P. (2003). Tetrahedron, 59, 7819-7858.]); Zhou et al. (2011[Zhou, Y., Armstrong, D. W., Zhang, Y. & Verkade, J. G. (2011). Tetrahedron Lett. 52, 1545-1548.]). For similar structure types, see: Kingston & Verkade (2005[Kingston, J. V. & Verkade, J. G. (2005). Inorg. Chem. Commun. 8, 643-646.]); Kisanga & Verkade (2001[Kisanga, P. B. & Verkade, J. G. (2001). Tetrahedron, 57, 467-475.]); Liu et al. (1999[Liu, X., Bai, Y. & Verkade, J. G. (1999). J. Organomet. Chem. 582, 16-24.], 2000[Liu, X., Ilankumaran, P., Guzei, I. A. & Verkade, J. G. (2000). J. Org. Chem. 65, 701-706.]); Mohan et al. (1996[Mohan, T., Arumugam, S., Wang, T., Jacobson, R. A. & Verkade, J. G. (1996). Heteroatom Chem. 7, 455-460.]); Thirupathi et al. (2003[Thirupathi, N., Liu, X. & Verkade, J. G. (2003). Inorg. Chem. 42, 389-397.]); Wroblewski et al. (1995[Wroblewski, A., Pinkas, J. & Verkade, J. G. (1995). Main Group Chem. 1, 69-79.]).

[Scheme 1]

Experimental

Crystal data
  • C18H40N4P+·Cl-·2H2O

  • Mr = 414.99

  • Triclinic, [P \overline 1]

  • a = 10.0945 (19) Å

  • b = 15.759 (3) Å

  • c = 16.122 (3) Å

  • [alpha] = 106.720 (8)°

  • [beta] = 92.259 (8)°

  • [gamma] = 90.616 (8)°

  • V = 2453.6 (8) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.954, Tmax = 0.967

  • 35181 measured reflections

  • 9856 independent reflections

  • 5364 reflections with I > 2[sigma](I)

  • Rint = 0.063

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.39 e Å-3

  • [Delta][rho]min = -0.31 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H101...Cl2i 0.84 (6) 2.61 (6) 3.426 (6) 164 (5)
O1-H102...Cl2ii 0.93 (9) 2.32 (9) 3.208 (6) 159 (7)
O2-H103...Cl2iii 0.85 (7) 2.60 (7) 3.412 (7) 161 (5)
O2-H104...Cl2ii 0.81 (8) 2.38 (9) 3.188 (6) 177 (8)
O3-H105...Cl1iii 0.86 (5) 2.45 (5) 3.263 (6) 159 (4)
O3-H106...Cl1iv 0.85 (4) 2.45 (4) 3.286 (6) 165 (4)
O4-H108...Cl1iii 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[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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.  [ISI] [CSD] [CrossRef] [ChemPort]
Kisanga, P. B. & Verkade, J. G. (2001). Tetrahedron, 57, 467-475.  [ISI] [CrossRef] [ChemPort]
Liu, X., Bai, Y. & Verkade, J. G. (1999). J. Organomet. Chem. 582, 16-24.  [CrossRef] [ChemPort]
Liu, X., Ilankumaran, P., Guzei, I. A. & Verkade, J. G. (2000). J. Org. Chem. 65, 701-706.  [CrossRef] [ChemPort]
Mohan, T., Arumugam, S., Wang, T., Jacobson, R. A. & Verkade, J. G. (1996). Heteroatom Chem. 7, 455-460.  [CrossRef] [ChemPort]
Raders, M. R. & Verkade, J. G. (2010). J. Org. Chem. 75, 5308-5311.  [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Tang, J.-S., Dopke, J. & Verkade, J. G. (1993). J. Am. Chem. Soc. 115, 5015-5020.  [CrossRef] [ChemPort] [ISI]
Thirupathi, N., Liu, X. & Verkade, J. G. (2003). Inorg. Chem. 42, 389-397.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Verkade, J. G. & Kisanga, P. (2003). Tetrahedron, 59, 7819-7858.  [ISI] [CrossRef] [ChemPort]
Wroblewski, A., Pinkas, J. & Verkade, J. G. (1995). Main Group Chem. 1, 69-79.  [ChemPort]
Zhou, Y., Armstrong, D. W., Zhang, Y. & Verkade, J. G. (2011). Tetrahedron Lett. 52, 1545-1548.  [ISI] [CrossRef] [ChemPort]


Acta Cryst (2012). E68, o3317  [ doi:10.1107/S1600536812045618 ]

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