Ammonium 2,5,8,11,21,24,27-octaoxatri­cyclo[26.4.0.012,17]­dotriaconta-1(32),12(17),13,15,28,30-hexaene hexa­fluoro­phosphate

Fallon, G.D.; Lau, V.-L.; Langford, S.J.

doi:10.1107/S1600536802003100

Ammonium 2,5,8,11,21,24,27-octaoxatricyclo[26.4.0.0^12,17]dotriaconta-1(32),12(17),13,15,28,30-hexaene hexafluorophosphate

G. D. Fallon, V.-L. Lau and S. J. Langford

Dibenzo-24-crown-8 crystallizes with ammonium hexafluorophosphate to produce a complex in which the ammonium ion is encapsulated by the crown ether, NH₄⁺·C₂₄H₃₂O₈·PF₆^-.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802003100/ww6007sup1.cif Contains datablocks k55_01, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536802003100/ww6007Isup2.hkl Contains datablock I

CCDC reference: 182635

checkCIF report

Key indicators

Single-crystal X-ray study
T = 123 K
Mean (C-C) = 0.003 Å
R factor = 0.051
wR factor = 0.132
Data-to-parameter ratio = 17.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

Comment top

The host–guest relationship between crown ethers and ammonium-based cationic components is an important concept in the generation of a number of supramolecular assemblies. From our perspective, this relationship may be useful in providing electronic and structural roles towards the self-assembly of supramolecular photosynthetic mimics (Duggan, 2001). Here, we report on the solid-state structure obtained between ammonium hexafluorophosphate and dibenzo-24-crown-8, (I).

The molecular structure of [(I)·NH₄]PF₆ is shown in Fig. 1 and 2. The ammonium cation lies within the cavity of the crown ether (Fig. 1) and is stabilized by a series of single (N1—H1d···O6 = 1.90 Å and N1—H1a···O2 = 1.91 Å) and bifocated (N1—H1b···O8 and N1—H1b···O1 2.11 and 2.48 Å, respectively; N1—H1c···O4 and N1—H1c···O5 = 2.08 and 2.48 Å, respectively) hydrogen-bonding interactions. The difference in size complementarity between the radius of the ammonium cation and the 24 C8 cavity causes the macrocycle to adopt a folded and twisted conformation, effectively encapsulating the ammonium cation (Fig. 2). This encapsulation is similar to that observed for Na⁺ with DB24C8 (Dapporto, 1998), but differs from the large volume of work now published on the interactions of DB24C8 with dialkylammonium salts (Ashton, 1997, 1998), or other alkali metal ions (Gallagher, 1991) in which relatively flat conformations are observed.

Experimental top

Colourless crystals of [(I)·NH₄]PF₆ suitable for X-ray analysis were grown by slow evaporation from a CD₃COCD₃ solution of ammonium hexafluorophosphate (1.6 mg, 9.82 mmol) and dibenzo-24-crown-8 (4.2 mg, 9.36 mmol).

Computing details top

Data collection: COLLECT (Nonius, 1997-2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor 1997); data reduction: HKL DENZO and SCALEPACK (Otwinowski & Minor 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. View of (I·NH₄)PF₆ (50% probability displacement ellipsoids)
	Fig. 2. Side view illustrating the encapsulating nature of the crown ether around the ammonium guest.

(I) top

Crystal data top

NH₄⁺·C₂₄H₃₂O₈·PF₆⁻	Z = 2
M_r = 611.51	F(000) = 640
Triclinic, P1	D_x = 1.461 Mg m⁻³
a = 10.1950 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.6379 (2) Å	Cell parameters from 16366 reflections
c = 14.5447 (3) Å	θ = 0.4–28.3°
α = 69.371 (1)°	µ = 0.19 mm⁻¹
β = 71.536 (1)°	T = 123 K
γ = 89.670 (1)°	Tabular, colourless
V = 1390.30 (5) Å³	0.2 × 0.12 × 0.08 mm

Data collection top

KappaCCD diffractometer	R_int = 0.044
CCD rotation images, thick slices [scan type available ?]	θ_max = 28.3°, θ_min = 2.8°
16366 measured reflections	h = −12→13
6721 independent reflections	k = −13→14
3813 reflections with I > 2σ(I)	l = −18→19

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.051	w = 1/[σ²(F_o²) + (0.0619P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.133	(Δ/σ)_max = 0.009
S = 0.97	Δρ_max = 0.64 e Å⁻³
6721 reflections	Δρ_min = −0.55 e Å⁻³
377 parameters

Crystal data top

NH₄⁺·C₂₄H₃₂O₈·PF₆⁻	γ = 89.670 (1)°
M_r = 611.51	V = 1390.30 (5) Å³
Triclinic, P1	Z = 2
a = 10.1950 (2) Å	Mo Kα radiation
b = 10.6379 (2) Å	µ = 0.19 mm⁻¹
c = 14.5447 (3) Å	T = 123 K
α = 69.371 (1)°	0.2 × 0.12 × 0.08 mm
β = 71.536 (1)°

Data collection top

KappaCCD diffractometer	3813 reflections with I > 2σ(I)
16366 measured reflections	R_int = 0.044
6721 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	Δρ_max = 0.64 e Å⁻³
6721 reflections	Δρ_min = −0.55 e Å⁻³
377 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.

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

	x	y	z	U_iso*/U_eq
C1	0.3129 (2)	−0.1603 (2)	0.46349 (16)	0.0207 (5)
C2	0.2641 (2)	−0.2965 (2)	0.50646 (17)	0.0258 (5)
H2	0.2659	−0.3447	0.4622	0.031*
C3	0.2125 (2)	−0.3635 (2)	0.61440 (18)	0.0285 (5)
H3	0.1785	−0.457	0.6436	0.034*
C4	0.2107 (2)	−0.2941 (2)	0.67843 (18)	0.0284 (5)
H4	0.1769	−0.3404	0.752	0.034*
C5	0.2579 (2)	−0.1570 (2)	0.63661 (17)	0.0254 (5)
H5	0.2555	−0.1097	0.6816	0.031*
C6	0.3086 (2)	−0.0886 (2)	0.52907 (16)	0.0220 (5)
C7	0.3315 (2)	0.1256 (2)	0.54566 (16)	0.0231 (5)
H7A	0.3773	0.0918	0.599	0.028*
H7B	0.2301	0.118	0.5819	0.028*
C8	0.3872 (2)	0.2705 (2)	0.47824 (17)	0.0264 (5)
H8A	0.3657	0.325	0.5229	0.032*
H8B	0.4898	0.2768	0.4486	0.032*
C9	0.1858 (2)	0.3367 (2)	0.42397 (18)	0.0289 (5)
H9A	0.1675	0.4266	0.3821	0.035*
H9B	0.1485	0.3255	0.4984	0.035*
C10	0.1133 (2)	0.2282 (2)	0.40712 (17)	0.0293 (5)
H10A	0.1347	0.1381	0.446	0.035*
H10B	0.0112	0.2296	0.4324	0.035*
C11	0.1237 (2)	0.1419 (2)	0.27621 (18)	0.0278 (5)
H11A	0.0239	0.1087	0.3152	0.033*
H11B	0.179	0.0674	0.2985	0.033*
C12	0.1506 (2)	0.1856 (2)	0.16160 (17)	0.0254 (5)
H12A	0.1222	0.1093	0.1454	0.03*
H12B	0.0959	0.2606	0.1392	0.03*
C13	0.3387 (2)	0.2886 (2)	−0.00041 (16)	0.0203 (5)
C14	0.2543 (2)	0.2851 (2)	−0.05749 (17)	0.0251 (5)
H14	0.1628	0.2383	−0.0231	0.03*
C15	0.3036 (2)	0.3505 (2)	−0.16579 (18)	0.0279 (5)
H15	0.2454	0.348	−0.205	0.033*
C16	0.4359 (2)	0.4185 (2)	−0.21610 (17)	0.0256 (5)
H16	0.4686	0.4636	−0.2898	0.031*
C17	0.5221 (2)	0.4209 (2)	−0.15839 (17)	0.0241 (5)
H17	0.6135	0.468	−0.1931	0.029*
C18	0.4754 (2)	0.3556 (2)	−0.05178 (16)	0.0206 (5)
C19	0.6980 (2)	0.4006 (2)	−0.04130 (16)	0.0227 (5)
H19A	0.7107	0.4966	−0.0884	0.027*
H19B	0.7409	0.3465	−0.0837	0.027*
C20	0.7664 (2)	0.3860 (2)	0.03955 (17)	0.0251 (5)
H20A	0.8675	0.4148	0.0032	0.03*
H20B	0.7292	0.4487	0.0756	0.03*
C21	0.8072 (2)	0.1501 (2)	0.07834 (18)	0.0269 (5)
H21A	0.8561	0.0941	0.1244	0.032*
H21B	0.8763	0.1936	0.0075	0.032*
C22	0.6964 (2)	0.0610 (2)	0.07462 (17)	0.0283 (5)
H22A	0.6451	0.1162	0.0302	0.034*
H22B	0.7392	−0.0061	0.045	0.034*
C23	0.4812 (2)	−0.0731 (2)	0.18246 (17)	0.0266 (5)
H23A	0.5059	−0.1257	0.1364	0.032*
H23B	0.4204	−0.0059	0.1578	0.032*
C24	0.4062 (2)	−0.1658 (2)	0.29223 (16)	0.0253 (5)
H24A	0.3213	−0.2147	0.2957	0.03*
H24B	0.4668	−0.2333	0.3168	0.03*
N1	0.4623 (2)	0.2082 (2)	0.24701 (16)	0.0218 (4)
O1	0.35901 (15)	0.04659 (14)	0.48033 (11)	0.0225 (3)
O2	0.33418 (14)	0.32964 (15)	0.39406 (11)	0.0254 (4)
O3	0.16171 (15)	0.25410 (15)	0.29787 (11)	0.0271 (4)
O4	0.29767 (14)	0.22981 (15)	0.10713 (11)	0.0232 (3)
O5	0.55144 (14)	0.35355 (15)	0.01218 (11)	0.0215 (3)
O6	0.74804 (15)	0.25306 (15)	0.11655 (11)	0.0237 (3)
O7	0.60376 (15)	−0.00615 (15)	0.17881 (11)	0.0264 (4)
O8	0.36844 (15)	−0.08689 (14)	0.35784 (11)	0.0234 (3)
F1	0.01733 (15)	0.67182 (18)	0.18470 (12)	0.0529 (5)
F2	0.17876 (14)	0.82921 (16)	0.17226 (11)	0.0459 (4)
F3	0.02872 (17)	0.86009 (18)	0.30988 (14)	0.0668 (5)
F4	−0.13337 (13)	0.70644 (15)	0.32083 (10)	0.0400 (4)
F5	−0.03158 (18)	0.88075 (17)	0.16863 (15)	0.0735 (6)
F6	0.07863 (18)	0.65261 (17)	0.32354 (14)	0.0674 (6)
P1	0.02327 (6)	0.76736 (6)	0.24695 (5)	0.02525 (17)
H1C	0.418 (3)	0.227 (3)	0.199 (2)	0.058 (9)*
H1D	0.562 (3)	0.224 (3)	0.211 (2)	0.042 (7)*
H1A	0.429 (3)	0.266 (3)	0.287 (2)	0.053 (8)*
H1B	0.436 (3)	0.122 (3)	0.288 (2)	0.043 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0187 (11)	0.0226 (13)	0.0177 (11)	0.0043 (9)	−0.0052 (9)	−0.0047 (10)
C2	0.0259 (12)	0.0245 (13)	0.0263 (13)	0.0026 (10)	−0.0088 (10)	−0.0086 (10)
C3	0.0271 (12)	0.0211 (13)	0.0295 (13)	0.0002 (10)	−0.0082 (11)	−0.0013 (11)
C4	0.0257 (12)	0.0279 (14)	0.0218 (12)	0.0005 (10)	−0.0054 (10)	−0.0001 (11)
C5	0.0238 (11)	0.0303 (14)	0.0229 (12)	0.0069 (10)	−0.0091 (10)	−0.0096 (10)
C6	0.0187 (11)	0.0194 (12)	0.0256 (12)	0.0043 (9)	−0.0080 (10)	−0.0053 (10)
C7	0.0268 (12)	0.0244 (13)	0.0207 (11)	0.0060 (10)	−0.0082 (10)	−0.0114 (10)
C8	0.0277 (12)	0.0283 (14)	0.0254 (12)	0.0051 (10)	−0.0103 (10)	−0.0112 (10)
C9	0.0267 (12)	0.0344 (14)	0.0243 (12)	0.0149 (11)	−0.0064 (11)	−0.0116 (11)
C10	0.0217 (11)	0.0398 (15)	0.0194 (12)	0.0055 (11)	−0.0016 (10)	−0.0074 (11)
C11	0.0216 (11)	0.0257 (13)	0.0305 (13)	0.0003 (10)	−0.0056 (10)	−0.0066 (11)
C12	0.0182 (11)	0.0265 (13)	0.0272 (13)	−0.0001 (10)	−0.0062 (10)	−0.0063 (10)
C13	0.0241 (11)	0.0163 (12)	0.0190 (11)	0.0049 (9)	−0.0050 (10)	−0.0067 (9)
C14	0.0240 (11)	0.0226 (13)	0.0304 (13)	0.0050 (10)	−0.0102 (11)	−0.0107 (11)
C15	0.0338 (13)	0.0273 (13)	0.0298 (13)	0.0077 (11)	−0.0185 (11)	−0.0121 (11)
C16	0.0359 (13)	0.0239 (13)	0.0197 (12)	0.0075 (10)	−0.0126 (11)	−0.0084 (10)
C17	0.0267 (12)	0.0215 (12)	0.0232 (12)	0.0049 (10)	−0.0078 (10)	−0.0079 (10)
C18	0.0230 (11)	0.0197 (12)	0.0220 (12)	0.0047 (9)	−0.0095 (10)	−0.0095 (10)
C19	0.0199 (11)	0.0238 (13)	0.0210 (11)	0.0022 (9)	−0.0040 (10)	−0.0068 (10)
C20	0.0238 (12)	0.0225 (13)	0.0290 (13)	0.0035 (10)	−0.0094 (10)	−0.0091 (10)
C21	0.0280 (12)	0.0248 (13)	0.0252 (12)	0.0087 (10)	−0.0056 (11)	−0.0092 (10)
C22	0.0345 (13)	0.0234 (13)	0.0205 (12)	0.0053 (10)	−0.0002 (11)	−0.0087 (10)
C23	0.0316 (13)	0.0269 (14)	0.0245 (12)	0.0050 (10)	−0.0102 (11)	−0.0124 (11)
C24	0.0313 (12)	0.0234 (13)	0.0234 (12)	0.0042 (10)	−0.0089 (11)	−0.0115 (10)
N1	0.0226 (11)	0.0204 (12)	0.0184 (10)	0.0037 (9)	−0.0038 (9)	−0.0051 (9)
O1	0.0263 (8)	0.0192 (8)	0.0200 (8)	0.0043 (7)	−0.0059 (7)	−0.0066 (7)
O2	0.0249 (8)	0.0265 (9)	0.0221 (8)	0.0060 (7)	−0.0053 (7)	−0.0081 (7)
O3	0.0286 (8)	0.0279 (9)	0.0211 (8)	0.0029 (7)	−0.0057 (7)	−0.0069 (7)
O4	0.0202 (8)	0.0248 (9)	0.0210 (8)	0.0008 (6)	−0.0051 (7)	−0.0056 (7)
O5	0.0192 (7)	0.0250 (9)	0.0195 (8)	0.0017 (6)	−0.0064 (6)	−0.0073 (7)
O6	0.0266 (8)	0.0221 (9)	0.0223 (8)	0.0058 (7)	−0.0079 (7)	−0.0083 (7)
O7	0.0268 (8)	0.0268 (9)	0.0215 (8)	0.0000 (7)	−0.0041 (7)	−0.0074 (7)
O8	0.0286 (8)	0.0205 (8)	0.0195 (8)	0.0042 (7)	−0.0061 (7)	−0.0073 (7)
F1	0.0375 (8)	0.0759 (12)	0.0536 (10)	−0.0070 (8)	0.0012 (8)	−0.0481 (9)
F2	0.0294 (8)	0.0660 (11)	0.0357 (8)	−0.0117 (7)	−0.0008 (7)	−0.0197 (8)
F3	0.0626 (11)	0.0683 (12)	0.0683 (12)	−0.0244 (9)	0.0108 (9)	−0.0524 (10)
F4	0.0315 (7)	0.0495 (10)	0.0339 (8)	−0.0119 (7)	0.0070 (6)	−0.0253 (7)
F5	0.0589 (11)	0.0520 (12)	0.0856 (14)	0.0115 (9)	−0.0358 (11)	0.0125 (10)
F6	0.0682 (12)	0.0492 (11)	0.0782 (13)	0.0054 (9)	−0.0482 (11)	0.0049 (9)
P1	0.0258 (3)	0.0247 (4)	0.0232 (3)	0.0022 (3)	−0.0058 (3)	−0.0086 (3)

Geometric parameters (Å, º) top

C1—O8	1.378 (2)	C15—C16	1.375 (3)
C1—C2	1.382 (3)	C15—H15	0.95
C1—C6	1.407 (3)	C16—C17	1.401 (3)
C2—C3	1.394 (3)	C16—H16	0.95
C2—H2	0.95	C17—C18	1.375 (3)
C3—C4	1.373 (3)	C17—H17	0.95
C3—H3	0.95	C18—O5	1.382 (2)
C4—C5	1.388 (3)	C19—O5	1.445 (2)
C4—H4	0.95	C19—C20	1.511 (3)
C5—C6	1.390 (3)	C19—H19A	0.99
C5—H5	0.95	C19—H19B	0.99
C6—O1	1.376 (3)	C20—O6	1.429 (3)
C7—O1	1.442 (2)	C20—H20A	0.99
C7—C8	1.501 (3)	C20—H20B	0.99
C7—H7A	0.99	C21—O6	1.443 (3)
C7—H7B	0.99	C21—C22	1.504 (3)
C8—O2	1.435 (2)	C21—H21A	0.99
C8—H8A	0.99	C21—H21B	0.99
C8—H8B	0.99	C22—O7	1.427 (3)
C9—O2	1.445 (2)	C22—H22A	0.99
C9—C10	1.504 (3)	C22—H22B	0.99
C9—H9A	0.99	C23—O7	1.419 (3)
C9—H9B	0.99	C23—C24	1.494 (3)
C10—O3	1.429 (3)	C23—H23A	0.99
C10—H10A	0.99	C23—H23B	0.99
C10—H10B	0.99	C24—O8	1.446 (2)
C11—O3	1.421 (3)	C24—H24A	0.99
C11—C12	1.495 (3)	C24—H24B	0.99
C11—H11A	0.99	N1—H1C	0.90 (3)
C11—H11B	0.99	N1—H1D	0.97 (3)
C12—O4	1.445 (2)	N1—H1A	0.97 (3)
C12—H12A	0.99	N1—H1B	0.88 (3)
C12—H12B	0.99	F1—P1	1.5938 (15)
C13—C14	1.381 (3)	F2—P1	1.5949 (14)
C13—O4	1.383 (2)	F3—P1	1.5758 (15)
C13—C18	1.409 (3)	F4—P1	1.5998 (14)
C14—C15	1.396 (3)	F5—P1	1.5789 (15)
C14—H14	0.95	F6—P1	1.5753 (15)

O8—C1—C2	124.16 (19)	C17—C18—O5	124.86 (19)
O8—C1—C6	116.02 (19)	C17—C18—C13	119.57 (18)
C2—C1—C6	119.82 (19)	O5—C18—C13	115.53 (18)
C1—C2—C3	120.3 (2)	O5—C19—C20	108.30 (17)
C1—C2—H2	119.8	O5—C19—H19A	110
C3—C2—H2	119.8	C20—C19—H19A	110
C4—C3—C2	119.9 (2)	O5—C19—H19B	110
C4—C3—H3	120.1	C20—C19—H19B	110
C2—C3—H3	120.1	H19A—C19—H19B	108.4
C3—C4—C5	120.6 (2)	O6—C20—C19	115.54 (18)
C3—C4—H4	119.7	O6—C20—H20A	108.4
C5—C4—H4	119.7	C19—C20—H20A	108.4
C4—C5—C6	120.1 (2)	O6—C20—H20B	108.4
C4—C5—H5	119.9	C19—C20—H20B	108.4
C6—C5—H5	119.9	H20A—C20—H20B	107.5
O1—C6—C5	124.42 (19)	O6—C21—C22	111.23 (17)
O1—C6—C1	116.31 (18)	O6—C21—H21A	109.4
C5—C6—C1	119.3 (2)	C22—C21—H21A	109.4
O1—C7—C8	108.56 (17)	O6—C21—H21B	109.4
O1—C7—H7A	110	C22—C21—H21B	109.4
C8—C7—H7A	110	H21A—C21—H21B	108
O1—C7—H7B	110	O7—C22—C21	107.73 (18)
C8—C7—H7B	110	O7—C22—H22A	110.2
H7A—C7—H7B	108.4	C21—C22—H22A	110.2
O2—C8—C7	115.49 (17)	O7—C22—H22B	110.2
O2—C8—H8A	108.4	C21—C22—H22B	110.2
C7—C8—H8A	108.4	H22A—C22—H22B	108.5
O2—C8—H8B	108.4	O7—C23—C24	108.98 (17)
C7—C8—H8B	108.4	O7—C23—H23A	109.9
H8A—C8—H8B	107.5	C24—C23—H23A	109.9
O2—C9—C10	110.67 (18)	O7—C23—H23B	109.9
O2—C9—H9A	109.5	C24—C23—H23B	109.9
C10—C9—H9A	109.5	H23A—C23—H23B	108.3
O2—C9—H9B	109.5	O8—C24—C23	109.02 (18)
C10—C9—H9B	109.5	O8—C24—H24A	109.9
H9A—C9—H9B	108.1	C23—C24—H24A	109.9
O3—C10—C9	107.83 (19)	O8—C24—H24B	109.9
O3—C10—H10A	110.1	C23—C24—H24B	109.9
C9—C10—H10A	110.1	H24A—C24—H24B	108.3
O3—C10—H10B	110.1	H1C—N1—H1D	109 (2)
C9—C10—H10B	110.1	H1C—N1—H1A	106 (2)
H10A—C10—H10B	108.5	H1D—N1—H1A	114 (2)
O3—C11—C12	108.88 (18)	H1C—N1—H1B	107 (2)
O3—C11—H11A	109.9	H1D—N1—H1B	111 (2)
C12—C11—H11A	109.9	H1A—N1—H1B	110 (2)
O3—C11—H11B	109.9	C6—O1—C7	116.35 (16)
C12—C11—H11B	109.9	C8—O2—C9	115.79 (16)
H11A—C11—H11B	108.3	C11—O3—C10	111.97 (17)
O4—C12—C11	108.60 (16)	C13—O4—C12	116.32 (15)
O4—C12—H12A	110	C18—O5—C19	115.06 (15)
C11—C12—H12A	110	C20—O6—C21	115.92 (16)
O4—C12—H12B	110	C23—O7—C22	112.34 (16)
C11—C12—H12B	110	C1—O8—C24	115.60 (16)
H12A—C12—H12B	108.4	F6—P1—F3	89.39 (11)
C14—C13—O4	123.93 (19)	F6—P1—F5	178.84 (11)
C14—C13—C18	119.9 (2)	F3—P1—F5	91.74 (11)
O4—C13—C18	116.13 (17)	F6—P1—F1	89.95 (10)
C13—C14—C15	119.9 (2)	F3—P1—F1	179.23 (10)
C13—C14—H14	120.1	F5—P1—F1	88.92 (10)
C15—C14—H14	120.1	F6—P1—F2	90.85 (9)
C16—C15—C14	120.4 (2)	F3—P1—F2	89.38 (9)
C16—C15—H15	119.8	F5—P1—F2	88.90 (9)
C14—C15—H15	119.8	F1—P1—F2	91.02 (8)
C15—C16—C17	119.8 (2)	F6—P1—F4	89.82 (9)
C15—C16—H16	120.1	F3—P1—F4	90.76 (8)
C17—C16—H16	120.1	F5—P1—F4	90.44 (9)
C18—C17—C16	120.4 (2)	F1—P1—F4	88.85 (8)
C18—C17—H17	119.8	F2—P1—F4	179.32 (9)
C16—C17—H17	119.8

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O1	0.88 (3)	2.48 (3)	3.038 (2)	122 (2)
N1—H1A···O2	0.97 (3)	1.91 (3)	2.848 (2)	163 (2)
N1—H1C···O4	0.90 (3)	2.08 (3)	2.973 (2)	168 (3)
N1—H1C···O5	0.90 (3)	2.48 (3)	3.035 (2)	120 (2)
N1—H1D···O6	0.97 (3)	1.90 (3)	2.862 (2)	168 (2)
N1—H1B···O8	0.88 (3)	2.11 (3)	2.977 (3)	168 (2)

Experimental details

Crystal data
Chemical formula	NH₄⁺·C₂₄H₃₂O₈·PF₆⁻
M_r	611.51
Crystal system, space group	Triclinic, P1
Temperature (K)	123
a, b, c (Å)	10.1950 (2), 10.6379 (2), 14.5447 (3)
α, β, γ (°)	69.371 (1), 71.536 (1), 89.670 (1)
V (Å³)	1390.30 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.2 × 0.12 × 0.08

Data collection
Diffractometer	KappaCCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	16366, 6721, 3813
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.133, 0.97
No. of reflections	6721
No. of parameters	377
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.64, −0.55

Computer programs: COLLECT (Nonius, 1997-2000), HKL SCALEPACK (Otwinowski & Minor 1997), HKL DENZO and SCALEPACK (Otwinowski & Minor 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).