4,7,13,18-Tetra­oxa-1,10-diazo­nia­bicyclo­[8.5.5]icosane hexa­fluorido­silicate

Sen Gupta, N.; Wragg, D.S.; Tilset, M.; Omtvedt, J.P.

doi:10.1107/S1600536811026006

organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Pages o1958-o1959

doi:10.1107/S1600536811026006

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4,7,13,18-Tetraoxa-1,10-diazoniabicyclo[8.5.5]icosane hexafluoridosilicate

Nalinava Sen Gupta,^a ^* David S. Wragg,^b Mats Tilset ^c and Jon Petter Omtvedt ^a

^aCentre for Accelerator Based Research and Energy Physics (SAFE), Department of Chemistry, University of Oslo, PO Box 1038 Blindern, Oslo 0318, Norway, ^binGAP Centre for Research Based Innovation, Center for Materials Science and Nanotechnology, Department of Chemistry, University of Oslo, PO Box 1033 Blindern, Oslo 0315, Norway, and ^cDepartment of Chemistry, University of Oslo, PO Box 1033 Blindern, Oslo 0315, Norway
^*Correspondence e-mail: n.s.gupta@kjemi.uio.no

(Received 29 March 2011; accepted 30 June 2011; online 9 July 2011)

The asymmetric unit of the title molecular salt, C₁₄H₃₀N₂O₄²⁺·SiF₆²⁻, contains half of both the anion and the cation, both ions being completed by a crystallographic twofold axis passing through the Si atom. The cation has a cage structure with the ammonium H atoms pointing into the cage. These H atoms are shielded from intermolecular interactions and form only intramolecular contacts. There are short intermolecular C—H⋯F interactions in the structure, but no conventional intermolecular hydrogen bonds.

Related literature

For related structures, see: Cos et al. (1982 ); Rehder & Wang (2003 ); Luger et al. (1991 ); Sen Gupta et al. (2011 ); Anderson et al. (2006 ); Braband et al. (2003 ); Llusar et al. (2001 ). For discussion of a cryptand as a molecular automatic titrator, see: Alibrandi et al. (2009 ). For NMR data, see: Macchioni et al. (2001 ); Christe & Wilson (1990 ).

Experimental

Crystal data

C₁₄H₃₀N₂O₄²⁺·SiF₆²⁻
M_r = 432.49
Orthorhombic, P b c n
a = 10.050 (5) Å
b = 23.218 (5) Å
c = 8.031 (5) Å
V = 1874.0 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 293 K
0.11 × 0.10 × 0.05 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.977, T_max = 0.990
9809 measured reflections
2305 independent reflections
1467 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.116
S = 1.02
2305 reflections
123 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2	0.91	2.19	2.701 (2)	115
N1—H1⋯O1	0.91	2.30	2.813 (2)	115
N1—H1⋯O1ⁱ	0.91	2.37	2.826 (2)	111
C1—H1B⋯F004ⁱⁱ	0.97	2.37	3.277 (3)	156
C011—H01B⋯F3ⁱⁱⁱ	0.97	2.50	3.381 (3)	151
C2—H2A⋯F005^iv	0.97	2.39	3.289 (3)	155
C014—H01C⋯F005	0.97	2.41	3.257 (3)	146
C3—H3A⋯F004^v	0.97	2.41	3.189 (3)	137
C3—H3B⋯F3ⁱⁱⁱ	0.97	2.17	3.129 (3)	169
C014—H01D⋯F3	0.97	2.50	3.039 (3)	115
C4—H4B⋯F005^v	0.97	2.52	3.368 (3)	147
Symmetry codes: (i) $[-x+2, y, -z+{\script{3\over 2}}]$ ; (ii) $[-x+1, y, -z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{3\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iv) $[x, -y, z+{\script{1\over 2}}]$ ; (v) x, y, z+1.

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Berndt, 1999 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811026006/fy2006sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811026006/fy2006Isup2.hkl

checkCIF report

Comment top

Compound (I) was obtained unintentionally as the product of the attempted synthesis of a metal-encrypted tungsten(VI) complex with the [2.1.1]cryptand, 4,7,13,18-tetraoxa-1,10-diazabicyclo[8.5.5]icosane. We suspect that WCl₆, being susceptable to hydrolysis, reacted with water that was present as a contaminant. Compound (I) was obtained by recrystallization of the crude reaction product from acetone. When the same product was recrystalized from methanol, a similar diprotonated cryptand salt with PF₆^- as the anion formed (Sen Gupta et al., 2011). The solvent used for recystallization was the only difference between the methods to obtain the two different crystals.

This structure was originally solved as a hexafluorophosphate salt, but the P—F bond lengths appeared unusually long and corresponded to typical Si—F rather than P—F bonds. The highest difference peak was close to H—N⁺, indicating that the occupancy of the H atom was higher than 0.5, which would be required to ensure charge neutrality in a PF₆^- salt. The most negative difference density was observed near the central P atom, showing that in reality there are less electrons there. Furthermore, refinement of the data with Si gave slightly lower R factors than with P. Though similar long P—F bonds are not unprecedented (Braband et al., 2003; Llusar et al., 2001), the above observations very strongly suggested that this was a diprotonated SiF₆^2- salt rather than a monoprotonated PF₆^- salt.

The presence of both anions in the reaction product was confirmed by ¹⁹F NMR data collected in a CD₃OD solution. The presence of the PF₆^- anion was indicated by a doublet at δ = -74.7 p.p.m. with ¹J(¹⁹F–³¹P) = 754 Hz (Macchioni et al., 2001). A small singlet peak at δ = -130.6 p.p.m. and a heteronuclear coupling constant ¹J(²⁹Si–¹⁹F) = 109 Hz were also observed and correspond to the SiF₆^2- anion (Christe & Wilson, 1990).

SiF₆^2- is assumed to be generated by the formation of HF upon the hydrolysis of PF₆^- and by the consequent reaction of HF with the silica of the glass. A smilar case was reported by Anderson et al. (2006).

In the crystal of compound (I), the two ammonium hydrogen atoms of the diprotonated cryptand cage are pointing inwards. Cryptands are known to form proton crypts, in which the protons are very efficiently concealed inside a tight molecular cavity. No exception is observed here: the ammonium hydrogen atoms are not involved in intermolecular hydrogen bonding. They only form intramolecular contacts with the oxygen atoms of the cryptand.

Related literature top

For related structures, see: Cos et al. (1982); Rehder & Wang (2003); Luger et al. (1991); Sen Gupta et al. (2011); Anderson et al. (2006); Braband et al. (2003); Llusar et al. (2001). For discussion of a cryptand as a molecular automatic titrator, see: Alibrandi et al. (2009). For NMR data, see: Macchioni et al. (2001); Christe & Wilson (1990).

Experimental top

Reagents were purchased from Sigma-Aldrich and were used without further purification. Reactions were carried out under inert conditions by Schlenk-line techniques. The metal chloride (WCl₆, 100 mg, 0.25 mmol) was allowed to stir for a minute in 10 ml toluene and then was reacted with a small excess of of AgPF₆ (381 mg, 1.51 mmol) to give AgCl as a precipitate and W(PF₆)₆ dissolved in solution. After 30 minutes stirring, the precipitate was allowed to settle. The solution was transferred under inert conditions by cannula technique and treated with the solution of [2.1.1]cryptand (66 µl, 0.25 mmol) in 5 ml toluene for 30 minutes. The crude reaction product was obtained as dirty yellow mass after drying the solvent. Portions of the product were recrystallized from acetone which produced crystal (I).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Berndt, 1999); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms. The hydrogen atoms attached to the carbons are omitted for clarity. Symmetry codes: (i) -x+1, y, -z+1/2; (ii) -x+2, y, -z+3/2.
	Fig. 2. Packing diagram for (I) viewed along the a axis. H atoms omitted for clarity.

4,7,13,18-Tetraoxa-1,10-diazoniabicyclo[8.5.5]icosane hexafluoridosilicate top

Crystal data top

C₁₄H₃₀N₂O₄²⁺·SiF₆²⁻	F(000) = 912
M_r = 432.49	D_x = 1.533 Mg m⁻³
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 2312 reflections
a = 10.050 (5) Å	θ = 2.2–28.0°
b = 23.218 (5) Å	µ = 0.21 mm⁻¹
c = 8.031 (5) Å	T = 293 K
V = 1874.0 (15) Å³	Block, colourless
Z = 4	0.11 × 0.10 × 0.05 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2305 independent reflections
Radiation source: sealed tube	1467 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ϕ and ω scans	θ_max = 28.8°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −11→13
T_min = 0.977, T_max = 0.990	k = −29→31
9809 measured reflections	l = −10→10

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0509P)² + 0.6523P] where P = (F_o² + 2F_c²)/3
2305 reflections	(Δ/σ)_max < 0.001
123 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₄H₃₀N₂O₄²⁺·SiF₆²⁻	V = 1874.0 (15) Å³
M_r = 432.49	Z = 4
Orthorhombic, Pbcn	Mo Kα radiation
a = 10.050 (5) Å	µ = 0.21 mm⁻¹
b = 23.218 (5) Å	T = 293 K
c = 8.031 (5) Å	0.11 × 0.10 × 0.05 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2305 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1467 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.990	R_int = 0.028
9809 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.116	H-atom parameters constrained
S = 1.02	Δρ_max = 0.32 e Å⁻³
2305 reflections	Δρ_min = −0.26 e Å⁻³
123 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Si1	0.5000	0.14596 (3)	0.2500	0.02931 (19)
F3	0.61848 (13)	0.19715 (5)	0.25800 (17)	0.0524 (3)
O2	0.86157 (15)	0.02390 (6)	0.76498 (17)	0.0421 (4)
F004	0.50972 (13)	0.14736 (7)	0.04208 (16)	0.0729 (5)
F005	0.61920 (12)	0.09635 (5)	0.2602 (2)	0.0668 (4)
O1	0.97909 (13)	0.14163 (5)	0.97904 (18)	0.0391 (3)
N1	0.79018 (16)	0.13502 (6)	0.72125 (19)	0.0341 (4)
H1	0.8702	0.1174	0.7367	0.041*
C5	0.9322 (2)	−0.02623 (8)	0.7128 (3)	0.0403 (5)
H5A	0.9389	−0.0267	0.5923	0.048*
H5B	0.8844	−0.0605	0.7477	0.048*
C1	0.6852 (2)	0.08871 (8)	0.7376 (3)	0.0450 (5)
H1A	0.6581	0.0853	0.8531	0.054*
H1B	0.6076	0.0991	0.6722	0.054*
C3	0.7786 (2)	0.18006 (8)	0.8537 (3)	0.0394 (5)
H3A	0.6854	0.1879	0.8757	0.047*
H3B	0.8200	0.2155	0.8160	0.047*
C011	0.9254 (2)	0.18663 (9)	0.5104 (2)	0.0412 (5)
H01A	0.9253	0.2032	0.3996	0.049*
H01B	0.9459	0.2168	0.5901	0.049*
C4	0.8453 (2)	0.15967 (10)	1.0105 (3)	0.0429 (5)
H4A	0.8456	0.1906	1.0917	0.051*
H4B	0.7952	0.1278	1.0569	0.051*
C2	0.7402 (2)	0.03213 (9)	0.6775 (3)	0.0483 (6)
H2A	0.6785	0.0011	0.7013	0.058*
H2B	0.7560	0.0333	0.5584	0.058*
C014	0.7927 (2)	0.16036 (9)	0.5484 (2)	0.0424 (5)
H01C	0.7736	0.1304	0.4677	0.051*
H01D	0.7241	0.1896	0.5391	0.051*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Si1	0.0274 (4)	0.0258 (3)	0.0347 (4)	0.000	0.0017 (3)	0.000
F3	0.0491 (8)	0.0408 (6)	0.0671 (8)	−0.0155 (6)	−0.0126 (6)	0.0053 (6)
O2	0.0468 (8)	0.0332 (7)	0.0463 (8)	0.0034 (6)	−0.0072 (7)	−0.0068 (6)
F004	0.0457 (8)	0.1356 (14)	0.0373 (7)	−0.0124 (8)	0.0033 (6)	−0.0186 (8)
F005	0.0401 (7)	0.0406 (7)	0.1199 (13)	0.0122 (6)	−0.0051 (8)	−0.0097 (8)
O1	0.0357 (8)	0.0381 (8)	0.0435 (8)	−0.0003 (6)	0.0016 (6)	0.0001 (6)
N1	0.0268 (8)	0.0330 (8)	0.0426 (9)	0.0010 (6)	0.0007 (7)	0.0030 (7)
C5	0.0537 (13)	0.0267 (9)	0.0406 (11)	−0.0044 (9)	0.0065 (9)	−0.0041 (7)
C1	0.0293 (10)	0.0426 (12)	0.0632 (14)	−0.0069 (9)	−0.0008 (10)	0.0046 (11)
C3	0.0383 (11)	0.0346 (10)	0.0454 (11)	0.0042 (9)	0.0074 (9)	0.0007 (8)
C011	0.0448 (12)	0.0429 (11)	0.0358 (10)	0.0049 (9)	0.0023 (9)	0.0081 (9)
C4	0.0388 (11)	0.0510 (13)	0.0390 (11)	0.0033 (9)	0.0084 (9)	0.0014 (9)
C2	0.0457 (13)	0.0414 (12)	0.0578 (13)	−0.0097 (10)	−0.0078 (11)	−0.0001 (10)
C014	0.0380 (11)	0.0505 (12)	0.0386 (11)	0.0045 (9)	−0.0064 (9)	0.0067 (9)

Geometric parameters (Å, º) top

Si1—F005ⁱ	1.6640 (13)	C1—C2	1.505 (3)
Si1—F005	1.6640 (13)	C1—H1A	0.9700
Si1—F004ⁱ	1.6730 (17)	C1—H1B	0.9700
Si1—F004	1.6730 (17)	C3—C4	1.503 (3)
Si1—F3	1.6836 (13)	C3—H3A	0.9700
Si1—F3ⁱ	1.6836 (13)	C3—H3B	0.9700
O2—C2	1.421 (3)	C011—O1ⁱⁱ	1.421 (2)
O2—C5	1.426 (2)	C011—C014	1.498 (3)
O1—C011ⁱⁱ	1.421 (2)	C011—H01A	0.9700
O1—C4	1.431 (2)	C011—H01B	0.9700
N1—C3	1.496 (2)	C4—H4A	0.9700
N1—C014	1.508 (2)	C4—H4B	0.9700
N1—C1	1.512 (2)	C2—H2A	0.9700
N1—H1	0.9100	C2—H2B	0.9700
C5—C5ⁱⁱ	1.488 (4)	C014—H01C	0.9700
C5—H5A	0.9700	C014—H01D	0.9700
C5—H5B	0.9700

F005ⁱ—Si1—F005	92.38 (10)	N1—C1—H1B	109.7
F005ⁱ—Si1—F004ⁱ	91.18 (8)	H1A—C1—H1B	108.2
F005—Si1—F004ⁱ	90.36 (8)	N1—C3—C4	109.91 (16)
F005ⁱ—Si1—F004	90.36 (8)	N1—C3—H3A	109.7
F005—Si1—F004	91.18 (8)	C4—C3—H3A	109.7
F004ⁱ—Si1—F004	177.77 (13)	N1—C3—H3B	109.7
F005ⁱ—Si1—F3	178.75 (7)	C4—C3—H3B	109.7
F005—Si1—F3	88.72 (7)	H3A—C3—H3B	108.2
F004ⁱ—Si1—F3	89.40 (7)	O1ⁱⁱ—C011—C014	106.85 (16)
F004—Si1—F3	89.03 (7)	O1ⁱⁱ—C011—H01A	110.4
F005ⁱ—Si1—F3ⁱ	88.72 (7)	C014—C011—H01A	110.4
F005—Si1—F3ⁱ	178.75 (7)	O1ⁱⁱ—C011—H01B	110.4
F004ⁱ—Si1—F3ⁱ	89.03 (7)	C014—C011—H01B	110.4
F004—Si1—F3ⁱ	89.40 (7)	H01A—C011—H01B	108.6
F3—Si1—F3ⁱ	90.18 (10)	O1—C4—C3	111.31 (16)
C2—O2—C5	113.08 (16)	O1—C4—H4A	109.4
C011ⁱⁱ—O1—C4	114.14 (15)	C3—C4—H4A	109.4
C3—N1—C014	112.51 (15)	O1—C4—H4B	109.4
C3—N1—C1	112.39 (16)	C3—C4—H4B	109.4
C014—N1—C1	111.66 (16)	H4A—C4—H4B	108.0
C3—N1—H1	106.6	O2—C2—C1	105.91 (17)
C014—N1—H1	106.6	O2—C2—H2A	110.6
C1—N1—H1	106.6	C1—C2—H2A	110.6
O2—C5—C5ⁱⁱ	109.75 (13)	O2—C2—H2B	110.6
O2—C5—H5A	109.7	C1—C2—H2B	110.6
C5ⁱⁱ—C5—H5A	109.7	H2A—C2—H2B	108.7
O2—C5—H5B	109.7	C011—C014—N1	111.18 (16)
C5ⁱⁱ—C5—H5B	109.7	C011—C014—H01C	109.4
H5A—C5—H5B	108.2	N1—C014—H01C	109.4
C2—C1—N1	109.68 (17)	C011—C014—H01D	109.4
C2—C1—H1A	109.7	N1—C014—H01D	109.4
N1—C1—H1A	109.7	H01C—C014—H01D	108.0
C2—C1—H1B	109.7

C2—O2—C5—C5ⁱⁱ	169.93 (19)	N1—C3—C4—O1	53.0 (2)
C3—N1—C1—C2	−148.05 (17)	C5—O2—C2—C1	−175.52 (16)
C014—N1—C1—C2	84.4 (2)	N1—C1—C2—O2	52.4 (2)
C014—N1—C3—C4	−150.55 (16)	O1ⁱⁱ—C011—C014—N1	60.8 (2)
C1—N1—C3—C4	82.4 (2)	C3—N1—C014—C011	76.0 (2)
C011ⁱⁱ—O1—C4—C3	88.0 (2)	C1—N1—C014—C011	−156.55 (16)

Symmetry codes: (i) −x+1, y, −z+1/2; (ii) −x+2, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.91	2.19	2.701 (2)	115
N1—H1···O1	0.91	2.30	2.813 (2)	115
N1—H1···O1ⁱⁱ	0.91	2.37	2.826 (2)	111
C1—H1B···F004ⁱ	0.97	2.37	3.277 (3)	156
C011—H01B···F3ⁱⁱⁱ	0.97	2.50	3.381 (3)	151
C2—H2A···F005^iv	0.97	2.39	3.289 (3)	155
C014—H01C···F005	0.97	2.41	3.257 (3)	146
C3—H3A···F004^v	0.97	2.41	3.189 (3)	137
C3—H3B···F3ⁱⁱⁱ	0.97	2.17	3.129 (3)	169
C014—H01D···F3	0.97	2.50	3.039 (3)	115
C4—H4B···F005^v	0.97	2.52	3.368 (3)	147

Symmetry codes: (i) −x+1, y, −z+1/2; (ii) −x+2, y, −z+3/2; (iii) −x+3/2, −y+1/2, z+1/2; (iv) x, −y, z+1/2; (v) x, y, z+1.

Experimental details

Crystal data
Chemical formula	C₁₄H₃₀N₂O₄²⁺·SiF₆²⁻
M_r	432.49
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	293
a, b, c (Å)	10.050 (5), 23.218 (5), 8.031 (5)
V (Å³)	1874.0 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.11 × 0.10 × 0.05

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.977, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	9809, 2305, 1467
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.677

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.116, 1.02
No. of reflections	2305
No. of parameters	123
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.26

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Berndt, 1999), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.91	2.19	2.701 (2)	115
N1—H1···O1	0.91	2.30	2.813 (2)	115
N1—H1···O1ⁱ	0.91	2.37	2.826 (2)	111
C1—H1B···F004ⁱⁱ	0.97	2.37	3.277 (3)	156
C011—H01B···F3ⁱⁱⁱ	0.97	2.50	3.381 (3)	151
C2—H2A···F005^iv	0.97	2.39	3.289 (3)	155
C014—H01C···F005	0.97	2.41	3.257 (3)	146
C3—H3A···F004^v	0.97	2.41	3.189 (3)	137
C3—H3B···F3ⁱⁱⁱ	0.97	2.17	3.129 (3)	169
C014—H01D···F3	0.97	2.50	3.039 (3)	115
C4—H4B···F005^v	0.97	2.52	3.368 (3)	147

Symmetry codes: (i) −x+2, y, −z+3/2; (ii) −x+1, y, −z+1/2; (iii) −x+3/2, −y+1/2, z+1/2; (iv) x, −y, z+1/2; (v) x, y, z+1.

Acknowledgements

The authors thank the Norwegian Research Council for financial support (project No. 177538).

References

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Volume 67| Part 8| August 2011| Pages o1958-o1959

doi:10.1107/S1600536811026006

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

4,7,13,18-Tetra­oxa-1,10-diazo­nia­bi­cyclo­[8.5.5]i­cosane hexa­fluorido­silicate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4,7,13,18-Tetraoxa-1,10-diazoniabicyclo[8.5.5]icosane hexafluoridosilicate