Tetra-n-butyl­ammonium hexa­fluoro­phosphate

The structure of the title compound, C₁₆H₃₆N⁺·PF₆^-, has been reported previously by Angaridis, Cotton & Petrukhina [Inorg. Chim. Acta (2001), 324, 318-323]. However, these authors found the PF₆^- ion to be heavily disordered and they did not publish any coordinates. We present here a redetermination of this structure, based on new intensity data and exhibiting no disorder.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.057
• wR factor = 0.159
• Data-to-parameter ratio = 15.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT244_ALERT_4_C Low  Solvent U(eq) as Compared to Neighbors  for         P1
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

Tetra-n-butylammonium hexafluorophosphate

Crystal data

C16H36N^+·PF6^−	F(000) = 832
Mr = 387.43	Dx = 1.344 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7863 reflections
a = 9.4057 (19) Å	θ = 2.6–24.8°
b = 13.593 (2) Å	µ = 0.20 mm^−1
c = 14.982 (3) Å	T = 173 K
β = 91.367 (16)°	Plate, colourless
V = 1914.9 (6) Å^3	0.29 × 0.14 × 0.12 mm
Z = 4

Data collection

Stoe IPDS-II two-circle diffractometer	1764 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.081
Graphite monochromator	θmax = 25.0°, θmin = 2.6°
ω scans	h = −11→11
13397 measured reflections	k = −16→16
3379 independent reflections	l = −17→16

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.159	H-atom parameters constrained
S = 0.91	w = 1/[σ^2(Fo^2) + (0.0896P)^2] where P = (Fo^2 + 2Fc^2)/3
3379 reflections	(Δ/σ)max < 0.001
217 parameters	Δρmax = 0.50 e Å^−3
0 restraints	Δρmin = −0.49 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
P1	0.24443 (10)	0.12522 (7)	0.31137 (7)	0.0441 (3)
F1	0.2138 (4)	0.0587 (3)	0.3918 (2)	0.1219 (13)
F2	0.2750 (4)	0.1899 (2)	0.2327 (2)	0.1228 (14)
F3	0.3726 (3)	0.1656 (3)	0.3637 (3)	0.1207 (14)
F4	0.1472 (3)	0.20655 (18)	0.35007 (19)	0.0761 (8)
F5	0.1156 (3)	0.0791 (2)	0.2639 (2)	0.1021 (11)
F6	0.3413 (2)	0.04459 (16)	0.27204 (15)	0.0609 (6)
N1	0.2683 (3)	0.47318 (19)	0.18806 (18)	0.0370 (6)
C11	0.1561 (4)	0.4550 (2)	0.1184 (2)	0.0404 (8)
H11A	0.0703	0.4928	0.1342	0.049*
H11B	0.1897	0.4812	0.0609	0.049*
C12	0.1151 (4)	0.3510 (3)	0.1053 (2)	0.0452 (8)
H12A	0.0999	0.3200	0.1641	0.054*
H12B	0.1933	0.3154	0.0762	0.054*
C13	−0.0166 (4)	0.3421 (3)	0.0494 (2)	0.0451 (8)
H13A	−0.0936	0.3802	0.0772	0.054*
H13B	0.0001	0.3708	−0.0102	0.054*
C14	−0.0625 (4)	0.2387 (3)	0.0387 (3)	0.0560 (10)
H14A	−0.1509	0.2362	0.0028	0.084*
H14B	−0.0786	0.2099	0.0976	0.084*
H14C	0.0116	0.2013	0.0086	0.084*
C21	0.2050 (4)	0.4524 (3)	0.2766 (2)	0.0415 (8)
H21A	0.1133	0.4879	0.2793	0.050*
H21B	0.1839	0.3812	0.2797	0.050*
C22	0.2921 (4)	0.4793 (3)	0.3566 (2)	0.0487 (9)
H22A	0.3105	0.5510	0.3570	0.058*
H22B	0.3846	0.4447	0.3557	0.058*
C23	0.2138 (5)	0.4510 (3)	0.4378 (3)	0.0622 (11)
H23A	0.1182	0.4814	0.4348	0.075*
H23B	0.2009	0.3787	0.4379	0.075*
C24	0.2860 (6)	0.4806 (3)	0.5226 (3)	0.0714 (13)
H24A	0.2289	0.4595	0.5730	0.107*
H24B	0.2968	0.5522	0.5239	0.107*
H24C	0.3799	0.4495	0.5268	0.107*
C31	0.3182 (4)	0.5769 (2)	0.1823 (2)	0.0395 (8)
H31A	0.3977	0.5859	0.2260	0.047*
H31B	0.3566	0.5875	0.1221	0.047*
C32	0.2098 (4)	0.6537 (2)	0.1987 (2)	0.0437 (8)
H32A	0.1738	0.6470	0.2600	0.052*
H32B	0.1286	0.6458	0.1560	0.052*
C33	0.2748 (4)	0.7528 (2)	0.1875 (3)	0.0465 (9)
H33A	0.3569	0.7596	0.2296	0.056*
H33B	0.3107	0.7588	0.1261	0.056*
C34	0.1719 (4)	0.8336 (3)	0.2037 (3)	0.0539 (10)
H34A	0.2192	0.8972	0.1961	0.081*
H34B	0.1371	0.8285	0.2646	0.081*
H34C	0.0917	0.8283	0.1610	0.081*
C41	0.3931 (3)	0.4071 (2)	0.1757 (2)	0.0381 (8)
H41A	0.4645	0.4210	0.2237	0.046*
H41B	0.3615	0.3382	0.1829	0.046*
C42	0.4629 (4)	0.4166 (2)	0.0883 (2)	0.0405 (8)
H42A	0.5051	0.4830	0.0833	0.049*
H42B	0.3907	0.4090	0.0396	0.049*
C43	0.5767 (4)	0.3408 (3)	0.0780 (3)	0.0472 (9)
H43A	0.6344	0.3582	0.0259	0.057*
H43B	0.6402	0.3420	0.1316	0.057*
C44	0.5203 (5)	0.2391 (3)	0.0655 (3)	0.0641 (11)
H44A	0.5998	0.1930	0.0600	0.096*
H44B	0.4603	0.2366	0.0112	0.096*
H44C	0.4639	0.2209	0.1171	0.096*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.0349 (5)	0.0445 (5)	0.0531 (6)	0.0009 (4)	0.0051 (4)	0.0012 (4)
F1	0.165 (3)	0.111 (3)	0.092 (2)	0.036 (2)	0.057 (2)	0.0431 (19)
F2	0.170 (3)	0.086 (2)	0.116 (3)	0.036 (2)	0.076 (2)	0.0587 (19)
F3	0.0566 (16)	0.148 (3)	0.157 (3)	0.0055 (18)	−0.0202 (18)	−0.091 (3)
F4	0.0586 (15)	0.0616 (15)	0.109 (2)	0.0122 (12)	0.0167 (14)	−0.0220 (14)
F5	0.0430 (14)	0.110 (2)	0.152 (3)	0.0030 (14)	−0.0113 (16)	−0.060 (2)
F6	0.0428 (12)	0.0596 (13)	0.0805 (16)	0.0147 (10)	0.0022 (11)	−0.0138 (12)
N1	0.0323 (14)	0.0387 (15)	0.0400 (15)	−0.0001 (12)	0.0040 (12)	0.0014 (12)
C11	0.0331 (17)	0.0470 (19)	0.0410 (18)	−0.0009 (15)	−0.0032 (15)	0.0002 (15)
C12	0.0388 (19)	0.0438 (19)	0.053 (2)	−0.0002 (15)	−0.0005 (16)	−0.0027 (16)
C13	0.0346 (17)	0.052 (2)	0.048 (2)	−0.0016 (16)	−0.0022 (16)	−0.0041 (16)
C14	0.048 (2)	0.060 (2)	0.060 (2)	−0.0044 (19)	−0.0014 (19)	−0.0142 (19)
C21	0.0377 (18)	0.0472 (19)	0.0399 (18)	−0.0042 (16)	0.0084 (15)	0.0002 (15)
C22	0.052 (2)	0.053 (2)	0.041 (2)	−0.0038 (18)	0.0053 (17)	−0.0011 (16)
C23	0.074 (3)	0.069 (3)	0.044 (2)	−0.009 (2)	0.012 (2)	0.001 (2)
C24	0.101 (4)	0.070 (3)	0.043 (2)	−0.006 (3)	0.004 (2)	0.000 (2)
C31	0.0370 (17)	0.0354 (17)	0.0462 (19)	−0.0032 (15)	0.0032 (15)	0.0025 (15)
C32	0.0390 (18)	0.0423 (19)	0.050 (2)	0.0004 (15)	0.0033 (16)	0.0009 (16)
C33	0.047 (2)	0.0400 (19)	0.052 (2)	−0.0037 (16)	0.0024 (18)	−0.0015 (16)
C34	0.060 (2)	0.044 (2)	0.058 (2)	0.0022 (19)	0.005 (2)	−0.0032 (17)
C41	0.0295 (16)	0.0421 (18)	0.0428 (18)	0.0055 (14)	0.0007 (14)	0.0022 (14)
C42	0.0381 (18)	0.0422 (18)	0.0414 (19)	0.0013 (15)	0.0033 (15)	−0.0001 (14)
C43	0.0376 (19)	0.055 (2)	0.050 (2)	0.0045 (17)	0.0062 (16)	0.0050 (17)
C44	0.066 (3)	0.052 (2)	0.075 (3)	0.009 (2)	0.017 (2)	−0.002 (2)

Geometric parameters (Å, º)

P1—F2	1.504 (3)	C23—H23A	0.9900
P1—F3	1.525 (3)	C23—H23B	0.9900
P1—F5	1.526 (3)	C24—H24A	0.9800
P1—F1	1.540 (3)	C24—H24B	0.9800
P1—F6	1.550 (2)	C24—H24C	0.9800
P1—F4	1.556 (2)	C31—C32	1.485 (5)
N1—C11	1.486 (4)	C31—H31A	0.9900
N1—C31	1.489 (4)	C31—H31B	0.9900
N1—C41	1.493 (4)	C32—C33	1.490 (5)
N1—C21	1.493 (4)	C32—H32A	0.9900
C11—C12	1.478 (5)	C32—H32B	0.9900
C11—H11A	0.9900	C33—C34	1.488 (5)
C11—H11B	0.9900	C33—H33A	0.9900
C12—C13	1.484 (5)	C33—H33B	0.9900
C12—H12A	0.9900	C34—H34A	0.9800
C12—H12B	0.9900	C34—H34B	0.9800
C13—C14	1.479 (5)	C34—H34C	0.9800
C13—H13A	0.9900	C41—C42	1.485 (5)
C13—H13B	0.9900	C41—H41A	0.9900
C14—H14A	0.9800	C41—H41B	0.9900
C14—H14B	0.9800	C42—C43	1.497 (5)
C14—H14C	0.9800	C42—H42A	0.9900
C21—C22	1.482 (5)	C42—H42B	0.9900
C21—H21A	0.9900	C43—C44	1.490 (5)
C21—H21B	0.9900	C43—H43A	0.9900
C22—C23	1.487 (5)	C43—H43B	0.9900
C22—H22A	0.9900	C44—H44A	0.9800
C22—H22B	0.9900	C44—H44B	0.9800
C23—C24	1.481 (6)	C44—H44C	0.9800
F2—P1—F3	91.7 (3)	C22—C23—H23A	108.8
F2—P1—F5	92.2 (2)	C24—C23—H23B	108.8
F3—P1—F5	176.0 (2)	C22—C23—H23B	108.8
F2—P1—F1	179.7 (2)	H23A—C23—H23B	107.7
F3—P1—F1	88.2 (3)	C23—C24—H24A	109.5
F5—P1—F1	87.8 (2)	C23—C24—H24B	109.5
F2—P1—F6	89.43 (16)	H24A—C24—H24B	109.5
F3—P1—F6	89.14 (15)	C23—C24—H24C	109.5
F5—P1—F6	89.98 (14)	H24A—C24—H24C	109.5
F1—P1—F6	90.29 (17)	H24B—C24—H24C	109.5
F2—P1—F4	90.12 (18)	C32—C31—N1	116.0 (3)
F3—P1—F4	91.00 (16)	C32—C31—H31A	108.3
F5—P1—F4	89.92 (15)	N1—C31—H31A	108.3
F1—P1—F4	90.16 (18)	C32—C31—H31B	108.3
F6—P1—F4	179.53 (16)	N1—C31—H31B	108.3
C11—N1—C31	109.6 (2)	H31A—C31—H31B	107.4
C11—N1—C41	111.1 (2)	C31—C32—C33	109.4 (3)
C31—N1—C41	108.2 (2)	C31—C32—H32A	109.8
C11—N1—C21	107.5 (2)	C33—C32—H32A	109.8
C31—N1—C21	111.3 (3)	C31—C32—H32B	109.8
C41—N1—C21	109.1 (2)	C33—C32—H32B	109.8
C12—C11—N1	115.5 (3)	H32A—C32—H32B	108.2
C12—C11—H11A	108.4	C34—C33—C32	112.2 (3)
N1—C11—H11A	108.4	C34—C33—H33A	109.2
C12—C11—H11B	108.4	C32—C33—H33A	109.2
N1—C11—H11B	108.4	C34—C33—H33B	109.2
H11A—C11—H11B	107.5	C32—C33—H33B	109.2
C11—C12—C13	111.4 (3)	H33A—C33—H33B	107.9
C11—C12—H12A	109.4	C33—C34—H34A	109.5
C13—C12—H12A	109.4	C33—C34—H34B	109.5
C11—C12—H12B	109.4	H34A—C34—H34B	109.5
C13—C12—H12B	109.4	C33—C34—H34C	109.5
H12A—C12—H12B	108.0	H34A—C34—H34C	109.5
C14—C13—C12	112.1 (3)	H34B—C34—H34C	109.5
C14—C13—H13A	109.2	C42—C41—N1	115.0 (3)
C12—C13—H13A	109.2	C42—C41—H41A	108.5
C14—C13—H13B	109.2	N1—C41—H41A	108.5
C12—C13—H13B	109.2	C42—C41—H41B	108.5
H13A—C13—H13B	107.9	N1—C41—H41B	108.5
C13—C14—H14A	109.5	H41A—C41—H41B	107.5
C13—C14—H14B	109.5	C41—C42—C43	111.4 (3)
H14A—C14—H14B	109.5	C41—C42—H42A	109.4
C13—C14—H14C	109.5	C43—C42—H42A	109.4
H14A—C14—H14C	109.5	C41—C42—H42B	109.4
H14B—C14—H14C	109.5	C43—C42—H42B	109.4
C22—C21—N1	116.6 (3)	H42A—C42—H42B	108.0
C22—C21—H21A	108.1	C44—C43—C42	113.5 (3)
N1—C21—H21A	108.1	C44—C43—H43A	108.9
C22—C21—H21B	108.1	C42—C43—H43A	108.9
N1—C21—H21B	108.1	C44—C43—H43B	108.9
H21A—C21—H21B	107.3	C42—C43—H43B	108.9
C21—C22—C23	108.9 (3)	H43A—C43—H43B	107.7
C21—C22—H22A	109.9	C43—C44—H44A	109.5
C23—C22—H22A	109.9	C43—C44—H44B	109.5
C21—C22—H22B	109.9	H44A—C44—H44B	109.5
C23—C22—H22B	109.9	C43—C44—H44C	109.5
H22A—C22—H22B	108.3	H44A—C44—H44C	109.5
C24—C23—C22	113.9 (4)	H44B—C44—H44C	109.5
C24—C23—H23A	108.8
C31—N1—C11—C12	169.3 (3)	C11—N1—C31—C32	62.3 (4)
C41—N1—C11—C12	49.8 (4)	C41—N1—C31—C32	−176.3 (3)
C21—N1—C11—C12	−69.6 (4)	C21—N1—C31—C32	−56.5 (4)
N1—C11—C12—C13	167.9 (3)	N1—C31—C32—C33	−178.1 (3)
C11—C12—C13—C14	−177.6 (3)	C31—C32—C33—C34	−179.6 (3)
C11—N1—C21—C22	−171.6 (3)	C11—N1—C41—C42	59.0 (3)
C31—N1—C21—C22	−51.5 (4)	C31—N1—C41—C42	−61.4 (4)
C41—N1—C21—C22	67.8 (4)	C21—N1—C41—C42	177.3 (3)
N1—C21—C22—C23	−178.5 (3)	N1—C41—C42—C43	−174.1 (3)
C21—C22—C23—C24	−176.0 (4)	C41—C42—C43—C44	71.0 (4)