1-Methyl-1-azonia-3,5-diaza-7-phosphatricyclo-[3.3.1.1]decane tetra-fluoro-borate.

The title compound, C(7)H(15)N(3)P(+)·BF(4) (-) or [PTA-Me][BF(4)], is the N-methyl-ated derivative of the well known water-soluble amino-phosphine 1,3,5-triaza-7-phosphaadamantane (PTA). The asymmetric unit consists of a cage-like cation [PTA-Me](+) and a disordered tetra-fluoro-borate anion; two F atoms are disordered equally over two sites. A network of weak inter-molecular C-H⋯F hydrogen bonds results in a three-dimensional supra-molecular 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 = 259.00

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.121

S = 1.05

1948 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.55 e Å−3

Δρmin = −0.36 e Å−3

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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C7H15N3P+·BF4–	F000 = 1072
Mr = 259.00	Dx = 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 = 3.4–25.2º
b = 11.6933 (18) Å	µ = 0.28 mm−1
c = 15.569 (2) Å	T = 150 (2) K
V = 2183.5 (6) Å3	Plate, colourless
Z = 8	0.16 × 0.12 × 0.10 mm

Bruker SMART CCD diffractometer	1948 independent reflections
Radiation source: fine-focus sealed tube	1391 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.061
T = 150(2) K	θmax = 25.3º
ω scans	θmin = 2.6º
Absorption correction: multi-scan(SADABS; Bruker, 2004)	h = −14→14
Tmin = 0.956, Tmax = 0.972	k = −14→13
10402 measured reflections	l = −18→15

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045	H-atom parameters constrained
wR(F2) = 0.121	w = 1/[σ2(Fo2) + (0.0512P)2 + 1.8936P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
1948 reflections	Δρmax = 0.55 e Å−3
164 parameters	Δρmin = −0.36 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq	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

	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)

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)

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

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) ; (ii) ; (iii) .