1-Methyl-1-azonia-3,5-diaza-7-phosphatricyclo­[3.3.1.13,7]decane tetra­fluoro­borate

Smoleński, P.; Kirillov, A.M.; Guedes da Silva, M.F.C.; Pombeiro, A.J.L.

doi:10.1107/S1600536808003401

organic compounds

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ISSN: 2056-9890

Volume 64| Part 3| March 2008| Page o556

doi:10.1107/S1600536808003401

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1-Methyl-1-azonia-3,5-diaza-7-phosphatricyclo[3.3.1.1^3,7]decane tetrafluoroborate

Piotr Smoleński,^a Alexander M. Kirillov,^a M. Fátima C. Guedes da Silva ^a,^b ^* and Armando J. L. Pombeiro ^a

^aCentro de Química Estrutural, Complexo Interdisciplinar, Instituto Superior Técnico, TU Lisbon, Av. Rovisco Pais, 1049-001 Lisbon, Portugal, and ^bUniversidade Lusófona de Humanidades e Tecnologias, ULHT Lisbon, Av. do Campo Grande, 376, 1749-024, Lisbon, Portugal
^*Correspondence e-mail: fatima.guedes@ist.utl.pt

(Received 24 January 2008; accepted 31 January 2008; online 6 February 2008)

The title compound, C₇H₁₅N₃P⁺·BF₄⁻ or [PTA-Me][BF₄], is the N-methylated derivative of the well known water-soluble aminophosphine 1,3,5-triaza-7-phosphaadamantane (PTA). The asymmetric unit consists of a cage-like cation [PTA-Me]⁺ and a disordered tetrafluoroborate anion; two F atoms are disordered equally over two sites. A network of weak intermolecular C—H⋯F hydrogen bonds results in a three-dimensional supramolecular assembly.

Related literature

For general background, see: Kirillov et al. (2007 ); Smoleński & Pombeiro (2008 ). For a comprehensive review of PTA chemistry, see: Phillips et al. (2004 ). For the synthesis of PTA and [PTA-Me]I, see: Daigle et al. (1974 ); Daigle (1998 ). For related organic structures, see: Jogun et al. (1978 ); Forward et al. (1996 ); Otto et al. (2005 ); Kirillov et al. (2008 ). For related metal–organic structures, see: Kovacs et al. (2004 ); Smoleński et al. (2003 ); Pruchnik et al. (1999 ).

Experimental

Crystal data

C₇H₁₅N₃P⁺·BF₄⁻
M_r = 259.00
Orthorhombic, P b c a
a = 11.994 (2) Å
b = 11.6933 (18) Å
c = 15.569 (2) Å
V = 2183.5 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 150 (2) K
0.16 × 0.12 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.956, T_max = 0.972
10402 measured reflections
1948 independent reflections
1391 reflections with I > 2σ(I)
R_int = 0.061

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.121
S = 1.05
1948 reflections
164 parameters
H-atom parameters constrained
Δρ_max = 0.55 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯F2ⁱ	0.99	2.54	3.438 (3)	151
C5—H5A⋯F4ⁱⁱ	0.99	2.35	3.314 (3)	166
C6—H6B⋯F4	0.99	2.46	3.364 (3)	152
C11—H11B⋯F2ⁱⁱⁱ	0.98	2.43	3.350 (4)	156
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+1, z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (iii) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: Mercury (Macrae et al., 2006 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808003401/hb2695sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808003401/hb2695Isup2.hkl

checkCIF report

Comment top

Being interested in the coordination chemistry of aminophosphine 1,3,5-triaza-7-phospha-adamantane (PTA) and related ligands (Kirillov et al., 2007; Smoleński & Pombeiro, 2008), we have prepared compound (I) from the analogous salt, [PTA-Me]I (Daigle et al., 1974; Daigle, 1998), to determine the coordination behaviour of the [PTA-Me]⁺ species in the absence of iodide ions.

Compound (I) crystallizes in an orthorhombic crystal system and its unit cell is composed of a cage-like N-methylated [PTA-Me]⁺ cation whose positive charge is balanced by a disordered tetrafluoroborate anion (Fig. 1). The title compound appears to be isostructural to the related salt (Jogun et al., 1978) that possesses the same anion but the P-methylated [PTA-Me]⁺ cation. The geometrical parameters for (I) are comparable to those of other compounds with N-methylated PTA cores, either free (Kirillov et al., 2008; Otto et al., 2005; Forward et al., 1996) or coordinated to the metal centres (Kovacs et al., 2004; Smoleński et al., 2003; Pruchnik et al., 1999).

In (I), the [PTA-Me]⁺ units are disposed relatively close to the [BF₄]^- anions, thus allowing their extensive assembling via weak intermolecular C—H···F hydrogen bonds [mean C···F separation = 3.366 (3) Å], resulting in the formation of a three-dimensional supramolecular framework (Table 1, Fig. 2).

Related literature top

For general background, see: Kirillov et al. (2007); Smoleński & Pombeiro (2008). For a comprehensive review of PTA chemistry, see: Phillips et al. (2004). For the synthesis of PTA and [PTA-Me]I, see: Daigle et al. (1974); Daigle (1998). For related organic structures, see: Jogun et al. (1978); Forward et al. (1996); Otto et al. (2005); Kirillov et al. (2008). For related metal–organic structures, see: Kovacs et al. (2004); Smoleński et al. (2003); Pruchnik et al. (1999).

Experimental top

An aqueous solution (25 ml) of [PTA-Me]I (1.00 mmol, 300 mg) and a methanolic (25 ml) solution of Tl[BF₄] (1.00 mmol, 300 mg) were combined at ambient temperature [Caution: Thallium compounds are highly toxic and thus must be handled with extreme caution]. The resulting white suspension was stirred for 15 min and then filtered off, giving a white powder of thallium iodide that was discarded. The colourless filtrate was evaporated in vacuo, resulting in a white solid. It was recrystallized from MeOH to furnish colourless plates of (I) in ca 80% yield (after isolation by filtration and drying in vacuo).

[PTA-Me][BF₄] is very soluble in middle-range polar solvents like Me₂CO, CHCl₃ and CH₂Cl₂, less soluble in H₂O, MeOH, EtOH and DMSO, and insoluble in C₆H₆, and Et₂O. FT–IR (KBr pellet), cm^-1: 2965 w, 2908 w, 1461 s, 1407 s, 1347 w, 1313 s, 1292 s, 1249 s, 1120 s, 1094 s br, 1023 s, 983 s, 920 s, 899 s, 815 s, 769 s, 748 m, 732 m, 687 w, 635 w, 557 s, 534 w and 440 w. ¹H NMR (300 MHz, D₂O, 25°C, Me₄Si): 4.86 and 4.75 (J(H^AH^B) = 11.4 Hz, 4H, NCH^AH^BN⁺), 4.52 and 4.36 (J(H^AH^B) = 13.8 Hz, 2H, NCH^AH^BN), 4.25 (d, ²J (H—P) = 6.8 Hz, 2H, PCH₂N⁺), 3.88 and 3.75 (J(H^AH^B) = 15.3 Hz, ³J(H^A—P) = 15.3 Hz, ³J(H^B—P) = 8.7 Hz, 4H, PCH^AH^BN), 2.66 (s, 3H, N⁺CH₃). ³¹P{¹H} NMR (121.4 MHz, D₂O, 25°C, 85% H₃PO₄): -85.7 (s).

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at the 20% probability level. H atoms are represented as spheres of arbitrary radius. The disordered F1 and F3 atoms are shown over their two positions.
	Fig. 2. Partial representation (view along the b axis) of the crystal packing diagram of (I) showing the generation of the three-dimensional supramolecular assembly via C—H···F hydrogen bonds and C···F short contacts (blue dotted lines). Hydrogen atoms and disordered F1B and F3B atoms are omitted for clarity. C, grey; N, blue; P, orange; F, light green; B, pink.

1-Methyl-1-azonia-3,5-diaza-7-phosphatricyclo[3.3.1.1^3,7]decane tetrafluoroborate top

Crystal data top

C₇H₁₅N₃P⁺·BF₄⁻	F(000) = 1072
M_r = 259.00	D_x = 1.576 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1323 reflections
a = 11.994 (2) Å	θ = 3.4–25.2°
b = 11.6933 (18) Å	µ = 0.28 mm⁻¹
c = 15.569 (2) Å	T = 150 K
V = 2183.5 (6) Å³	Plate, colourless
Z = 8	0.16 × 0.12 × 0.10 mm

Data collection top

Bruker SMART CCD diffractometer	1948 independent reflections
Radiation source: fine-focus sealed tube	1391 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.061
ω scans	θ_max = 25.3°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −14→14
T_min = 0.956, T_max = 0.972	k = −14→13
10402 measured reflections	l = −18→15

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.121	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0512P)² + 1.8936P] where P = (F_o² + 2F_c²)/3
1948 reflections	(Δ/σ)_max < 0.001
164 parameters	Δρ_max = 0.55 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³
0 constraints

Crystal data top

C₇H₁₅N₃P⁺·BF₄⁻	V = 2183.5 (6) Å³
M_r = 259.00	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 11.994 (2) Å	µ = 0.28 mm⁻¹
b = 11.6933 (18) Å	T = 150 K
c = 15.569 (2) Å	0.16 × 0.12 × 0.10 mm

Data collection top

Bruker SMART CCD diffractometer	1948 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	1391 reflections with I > 2σ(I)
T_min = 0.956, T_max = 0.972	R_int = 0.061
10402 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.121	H-atom parameters constrained
S = 1.05	Δρ_max = 0.55 e Å⁻³
1948 reflections	Δρ_min = −0.36 e Å⁻³
164 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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	Occ. (<1)
C1	0.5509 (2)	0.7943 (2)	0.68018 (19)	0.0248 (7)
H1A	0.5329	0.8736	0.6627	0.030*
H1B	0.6303	0.7806	0.6663	0.030*
C2	0.3782 (2)	0.7850 (2)	0.79565 (18)	0.0245 (7)
H2A	0.3505	0.7667	0.8539	0.029*
H2B	0.3533	0.8635	0.7815	0.029*
C3	0.5459 (2)	0.6251 (2)	0.80269 (18)	0.0253 (7)
H3A	0.6251	0.6043	0.7937	0.030*
H3B	0.5247	0.5997	0.8611	0.030*
C4	0.5074 (2)	0.5884 (2)	0.65244 (18)	0.0219 (6)
H4A	0.4671	0.5360	0.6133	0.026*
H4B	0.5883	0.5749	0.6448	0.026*
C5	0.3552 (2)	0.7325 (2)	0.64672 (18)	0.0211 (6)
H5A	0.3364	0.8136	0.6357	0.025*
H5B	0.3100	0.6848	0.6074	0.025*
C6	0.3583 (2)	0.5857 (2)	0.75217 (18)	0.0216 (6)
H6A	0.3384	0.5678	0.8124	0.026*
H6B	0.3146	0.5344	0.7145	0.026*
C11	0.5016 (3)	0.7311 (3)	0.53413 (18)	0.0295 (7)
H11A	0.4557	0.6780	0.5006	0.044*
H11B	0.5806	0.7173	0.5217	0.044*
H11C	0.4824	0.8099	0.5187	0.044*
B1	0.2262 (3)	0.4814 (3)	0.4904 (2)	0.0266 (8)
N1	0.48031 (17)	0.71288 (17)	0.62773 (13)	0.0146 (5)
N2	0.32749 (18)	0.70450 (19)	0.73373 (14)	0.0199 (5)
N3	0.47713 (18)	0.56276 (18)	0.73947 (14)	0.0190 (5)
F1A	0.1098 (3)	0.5043 (4)	0.4732 (3)	0.0580 (13)	0.59
F2	0.23739 (16)	0.37060 (14)	0.46049 (11)	0.0376 (5)
F3A	0.2858 (5)	0.5568 (4)	0.4471 (3)	0.0634 (14)	0.59
F4	0.2252 (2)	0.48727 (18)	0.57697 (12)	0.0627 (7)
P1	0.53278 (7)	0.78233 (7)	0.79717 (5)	0.0275 (2)
F1B	0.3444 (5)	0.5214 (6)	0.4871 (5)	0.071 (2)	0.41
F3B	0.1703 (10)	0.5502 (6)	0.4431 (5)	0.096 (3)	0.41

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0204 (14)	0.0198 (15)	0.0343 (18)	−0.0049 (12)	−0.0006 (13)	0.0022 (12)
C2	0.0265 (15)	0.0223 (15)	0.0246 (16)	0.0008 (12)	0.0046 (13)	−0.0034 (12)
C3	0.0204 (15)	0.0314 (16)	0.0240 (16)	−0.0016 (12)	−0.0053 (13)	0.0056 (13)
C4	0.0266 (15)	0.0158 (14)	0.0233 (17)	0.0058 (12)	0.0027 (12)	0.0003 (11)
C5	0.0187 (14)	0.0220 (15)	0.0225 (16)	0.0024 (11)	−0.0058 (12)	0.0006 (12)
C6	0.0184 (14)	0.0244 (16)	0.0219 (15)	−0.0034 (12)	0.0007 (12)	0.0028 (12)
C11	0.0391 (17)	0.0301 (17)	0.0193 (17)	0.0029 (14)	0.0054 (13)	0.0036 (13)
B1	0.039 (2)	0.0219 (18)	0.0187 (19)	0.0019 (16)	0.0014 (15)	−0.0018 (14)
N1	0.0174 (11)	0.0138 (11)	0.0126 (12)	−0.0002 (9)	0.0006 (9)	0.0028 (8)
N2	0.0176 (11)	0.0219 (12)	0.0203 (12)	−0.0006 (9)	0.0009 (10)	0.0008 (10)
N3	0.0215 (12)	0.0179 (12)	0.0177 (13)	0.0010 (10)	−0.0011 (10)	0.0039 (9)
F1A	0.039 (2)	0.044 (3)	0.091 (4)	0.0133 (19)	−0.020 (2)	−0.007 (2)
F2	0.0468 (12)	0.0268 (10)	0.0393 (12)	0.0008 (8)	−0.0028 (9)	−0.0112 (8)
F3A	0.085 (4)	0.045 (3)	0.060 (3)	−0.027 (3)	0.034 (3)	0.009 (2)
F4	0.120 (2)	0.0407 (12)	0.0273 (12)	−0.0117 (13)	−0.0007 (12)	−0.0048 (9)
P1	0.0306 (4)	0.0273 (4)	0.0244 (5)	−0.0070 (3)	−0.0052 (3)	−0.0014 (3)
F1B	0.044 (4)	0.075 (5)	0.094 (6)	−0.032 (3)	0.031 (4)	−0.057 (4)
F3B	0.165 (10)	0.047 (5)	0.075 (6)	0.046 (6)	−0.072 (6)	−0.005 (4)

Geometric parameters (Å, º) top

C1—N1	1.514 (3)	C5—N1	1.547 (3)
C1—P1	1.840 (3)	C5—H5A	0.9900
C1—H1A	0.9900	C5—H5B	0.9900
C1—H1B	0.9900	C6—N3	1.463 (3)
C2—N2	1.479 (3)	C6—N2	1.466 (3)
C2—P1	1.854 (3)	C6—H6A	0.9900
C2—H2A	0.9900	C6—H6B	0.9900
C2—H2B	0.9900	C11—N1	1.495 (3)
C3—N3	1.477 (3)	C11—H11A	0.9800
C3—P1	1.847 (3)	C11—H11B	0.9800
C3—H3A	0.9900	C11—H11C	0.9800
C3—H3B	0.9900	B1—F3B	1.281 (7)
C4—N3	1.434 (3)	B1—F3A	1.319 (5)
C4—N1	1.540 (3)	B1—F4	1.350 (4)
C4—H4A	0.9900	B1—F2	1.383 (4)
C4—H4B	0.9900	B1—F1A	1.447 (5)
C5—N2	1.433 (4)	B1—F1B	1.493 (7)

N1—C1—P1	114.83 (18)	N1—C11—H11A	109.5
N1—C1—H1A	108.6	N1—C11—H11B	109.5
P1—C1—H1A	108.6	H11A—C11—H11B	109.5
N1—C1—H1B	108.6	N1—C11—H11C	109.5
P1—C1—H1B	108.6	H11A—C11—H11C	109.5
H1A—C1—H1B	107.5	H11B—C11—H11C	109.5
N2—C2—P1	114.14 (18)	F3B—B1—F3A	64.6 (6)
N2—C2—H2A	108.7	F3B—B1—F4	122.5 (5)
P1—C2—H2A	108.7	F3A—B1—F4	118.7 (4)
N2—C2—H2B	108.7	F3B—B1—F2	116.5 (4)
P1—C2—H2B	108.7	F3A—B1—F2	113.7 (3)
H2A—C2—H2B	107.6	F4—B1—F2	112.6 (3)
N3—C3—P1	114.38 (18)	F3B—B1—F1A	43.2 (5)
N3—C3—H3A	108.7	F3A—B1—F1A	107.7 (4)
P1—C3—H3A	108.7	F4—B1—F1A	99.6 (3)
N3—C3—H3B	108.7	F2—B1—F1A	101.8 (3)
P1—C3—H3B	108.7	F3B—B1—F1B	106.3 (7)
H3A—C3—H3B	107.6	F3A—B1—F1B	42.2 (3)
N3—C4—N1	112.3 (2)	F4—B1—F1B	91.5 (4)
N3—C4—H4A	109.1	F2—B1—F1B	101.0 (3)
N1—C4—H4A	109.1	F1A—B1—F1B	148.4 (5)
N3—C4—H4B	109.1	C11—N1—C1	109.9 (2)
N1—C4—H4B	109.1	C11—N1—C4	110.0 (2)
H4A—C4—H4B	107.9	C1—N1—C4	110.0 (2)
N2—C5—N1	111.8 (2)	C11—N1—C5	109.3 (2)
N2—C5—H5A	109.2	C1—N1—C5	110.3 (2)
N1—C5—H5A	109.2	C4—N1—C5	107.28 (19)
N2—C5—H5B	109.2	C5—N2—C6	110.1 (2)
N1—C5—H5B	109.2	C5—N2—C2	112.1 (2)
H5A—C5—H5B	107.9	C6—N2—C2	111.8 (2)
N3—C6—N2	113.1 (2)	C4—N3—C6	109.6 (2)
N3—C6—H6A	109.0	C4—N3—C3	112.6 (2)
N2—C6—H6A	109.0	C6—N3—C3	111.3 (2)
N3—C6—H6B	109.0	C1—P1—C3	96.42 (13)
N2—C6—H6B	109.0	C1—P1—C2	95.98 (13)
H6A—C6—H6B	107.8	C3—P1—C2	95.91 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···F2ⁱ	0.99	2.54	3.438 (3)	151
C5—H5A···F4ⁱⁱ	0.99	2.35	3.314 (3)	166
C6—H6B···F4	0.99	2.46	3.364 (3)	152
C11—H11B···F2ⁱⁱⁱ	0.98	2.43	3.350 (4)	156

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

Experimental details

Crystal data
Chemical formula	C₇H₁₅N₃P⁺·BF₄⁻
M_r	259.00
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	150
a, b, c (Å)	11.994 (2), 11.6933 (18), 15.569 (2)
V (Å³)	2183.5 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.16 × 0.12 × 0.10

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.956, 0.972
No. of measured, independent and observed [I > 2σ(I)] reflections	10402, 1948, 1391
R_int	0.061
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.121, 1.05
No. of reflections	1948
No. of parameters	164
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.55, −0.36

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2006).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···F2ⁱ	0.99	2.54	3.438 (3)	151
C5—H5A···F4ⁱⁱ	0.99	2.35	3.314 (3)	166
C6—H6B···F4	0.99	2.46	3.364 (3)	152
C11—H11B···F2ⁱⁱⁱ	0.98	2.43	3.350 (4)	156

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

Acknowledgements

This work was supported by the Foundation for Science and Technology (FCT) and its POCI 2010 programme (FEDER funded).

References

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

1-Methyl-1-azonia-3,5-di­aza-7-phosphatri­cyclo­[3.3.1.13,7]decane tetra­fluoro­borate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1-Methyl-1-azonia-3,5-diaza-7-phosphatricyclo[3.3.1.1^3,7]decane tetrafluoroborate