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Volume 69 
Part 12 
Pages o1739-o1740  
December 2013  

Received 17 October 2013
Accepted 27 October 2013
Online 6 November 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.003 Å
Disorder in main residue
R = 0.044
wR = 0.125
Data-to-parameter ratio = 15.6
Details
Open access

N1-(Thio­phen-2-ylmeth­yl)-N3,N3-bis­[3-(thio­phen-2-yl­methyl­ammonio)­prop­yl]propane-1,3-di­ammonium hexa­fluorido­silicate methanol tris­olvate

aDepartment of Chemistry and Biochemistry, Jackson State University, Jackson, MS 39217, USA, and bDepartment of Chemistry and Biochemistry, University of Oklahoma, Norman, OK 73019, USA
Correspondence e-mail: alamgir.hossain@jsums.edu

In the title compound, C24H40N4S34+·2SiF62-·3CH3OH, the central tertiary amine function is protonated and is connected to three thio­phen-2-yl­methyl­amino-n-propyl groups, forming the arms of a T-shaped cation that has two pockets. Each arm contains one protonated secondary amine function, and each pocket is occupied by one SiF62- anion bonded via two N-H...F inter­actions with the protonated amine group on the middle arm, while two methanol solvent mol­ecules are N-H...O hydrogen-bonded with the other secondary protonated amine groups on the side arms. Weak O-H...O and O-H...F hydrogen bonds between the solvent mol­ecules and between the solvent mol­ecules and the anions, respectively, are also observed. All three thio­phene groups in the arms are disordered over two sets of sites, with occupancy ratios of 0.828 (3):0.172 (3), 0.910 (2):0.090 (2) and 0.890 (3):0.110 (3).

Related literature

For background to polyamine-based mol­ecules, see: McKee et al. (2003[McKee, V., Nelson, J. & Town, R. M. (2003). Chem. Soc. Rev., 32, 309-325.]); Hossain (2008[Hossain, M. A. (2008). Curr. Org. Chem. 12, 1231-1256.]); Mendy et al. (2010[Mendy, J. S., Pilate, M. L., Horne, T., Day, V. W. & Hossain, M. A. (2010). Chem. Commun. 46, 6084-6086.]). For our previous work on this class of compound, see: Isiklan et al. (2011[Isiklan, M., Saeed, M. A., Pramanik, A., Wong, B. M., Fronczek, F. R. & Hossain, M. A. (2011). Cryst. Growth Des. 11, 959-963.]); Hossain et al. (2011[Hossain, M. A., Isiklan, M., Pramanik, A., Saeed, M. A. & Fronczek, F. R. (2011). Cryst. Growth Des. 12, 567-571.]). For related structures, see: Hossain et al. (2012[Hossain, M. A., Saeed, M. A., Pramanik, A., Wong, B. M., Haque, S. A. & Powell, D. R. (2012). J. Am. Chem. Soc. 134, 11892-11895.]); Pilate et al. (2010[Pilate, M. L., Blount, H., Fronczek, F. R. & Hossain, M. A. (2010). Acta Cryst. E66, o1833-o1834.]).

[Scheme 1]

Experimental

Crystal data
  • C24H40N4S34+·2SiF62-·3CH4O

  • Mr = 861.09

  • Triclinic, [P \overline 1]

  • a = 8.4854 (4) Å

  • b = 12.5107 (6) Å

  • c = 18.9003 (10) Å

  • [alpha] = 89.024 (2)°

  • [beta] = 87.750 (2)°

  • [gamma] = 72.206 (3)°

  • V = 1908.94 (16) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.35 mm-1

  • T = 100 K

  • 0.58 × 0.16 × 0.03 mm

Data collection
  • Bruker APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2002[Bruker (2002). SADABS. Bruker AXS, Inc., Madison, Wisconsin, USA.]) Tmin = 0.822, Tmax = 0.990

  • 25975 measured reflections

  • 9447 independent reflections

  • 7815 reflections with I > 2[sigma](I)

  • Rint = 0.021

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.125

  • S = 1.00

  • 9447 reflections

  • 604 parameters

  • 642 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.94 e Å-3

  • [Delta][rho]min = -0.80 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...F4Di 0.90 (3) 2.51 (2) 3.171 (2) 131.3 (18)
N1-H1...F5Di 0.90 (3) 2.54 (2) 3.2005 (19) 131.1 (19)
N1-H1...F6Di 0.90 (2) 1.91 (2) 2.7810 (18) 162 (2)
N5A-H5A1...F1D 0.82 (2) 2.02 (2) 2.775 (2) 153 (2)
N5A-H5A1...F6D 0.82 (2) 2.44 (2) 2.985 (2) 125 (2)
N5A-H5A2...F3E 0.83 (2) 1.94 (2) 2.759 (2) 172 (2)
N5A-H5A2...F4E 0.83 (2) 2.63 (2) 3.029 (2) 111 (2)
N5B-H5B1...F1Eii 0.82 (2) 1.92 (2) 2.736 (2) 170 (2)
N5B-H5B1...F2Eii 0.82 (2) 2.47 (2) 2.969 (2) 120 (2)
N5B-H5B2...O1F 0.84 (2) 1.98 (2) 2.790 (2) 163 (2)
N5C-H5C1...F5Ei 0.84 (2) 2.00 (2) 2.828 (2) 171 (3)
N5C-H5C1...F1Ei 0.84 (2) 2.41 (2) 2.932 (2) 121 (2)
N5C-H5C2...O3F 0.86 (2) 1.92 (2) 2.758 (3) 168 (3)
O1F-H1F...F3Di 0.84 1.95 2.7374 (19) 156
O1F-H1F...F4Di 0.84 2.43 3.144 (2) 139
O3F-H3F...F6E 0.84 2.13 2.974 (3) 180
O3F-H3F...F4E 0.84 2.61 3.118 (3) 120
O5F-H5F...O3F 0.84 2.39 3.226 (5) 179
Symmetry codes: (i) x-1, y, z; (ii) -x+1, -y, -z+1.

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS, Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART and SAINT. 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: WM2779 ).


Acknowledgements

The National Science Foundation is acknowledged for a CAREER award (CHE-1056927) to MAH. The NMR core facility at Jackson State University was supported by the National Institutes of Health (G12RR013459). DNC was supported by the National Institutes of Health (NIH)-Minority Access to Research Careers/Undergraduate Student Training in Academic Research (NIH-MARC/U*STAR) Program (Grant No. 5 T34GM007672-34). The authors thank the National Science Foundation (CHE-0130835) and the University of Oklahoma for funds to acquire the diffractometer used in this work.

References

Bruker (2002). SADABS. Bruker AXS, Inc., Madison, Wisconsin, USA.
Bruker (2007). SMART and SAINT. Bruker AXS, Inc., Madison, Wisconsin, USA.
Hossain, M. A. (2008). Curr. Org. Chem. 12, 1231-1256.  [Web of Science] [CrossRef] [ChemPort]
Hossain, M. A., Isiklan, M., Pramanik, A., Saeed, M. A. & Fronczek, F. R. (2011). Cryst. Growth Des. 12, 567-571.  [CSD] [CrossRef]
Hossain, M. A., Saeed, M. A., Pramanik, A., Wong, B. M., Haque, S. A. & Powell, D. R. (2012). J. Am. Chem. Soc. 134, 11892-11895.  [Web of Science] [CSD] [CrossRef] [ChemPort] [PubMed]
Isiklan, M., Saeed, M. A., Pramanik, A., Wong, B. M., Fronczek, F. R. & Hossain, M. A. (2011). Cryst. Growth Des. 11, 959-963.  [PubMed]
McKee, V., Nelson, J. & Town, R. M. (2003). Chem. Soc. Rev., 32, 309-325.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Mendy, J. S., Pilate, M. L., Horne, T., Day, V. W. & Hossain, M. A. (2010). Chem. Commun. 46, 6084-6086.  [CSD] [CrossRef] [ChemPort]
Pilate, M. L., Blount, H., Fronczek, F. R. & Hossain, M. A. (2010). Acta Cryst. E66, o1833-o1834.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1739-o1740   [ doi:10.1107/S1600536813029565 ]

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