Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802003100/ww6007sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802003100/ww6007Isup2.hkl |
CCDC reference: 182635
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
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).
The H atoms were included in the riding-model approximation, except those of the ammonium ion which were located by difference fourier and refined.
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).
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. |
NH4+·C24H32O8·PF6− | Z = 2 |
Mr = 611.51 | F(000) = 640 |
Triclinic, P1 | Dx = 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 |
KappaCCD diffractometer | Rint = 0.044 |
CCD rotation images, thick slices [scan type available ?] | θmax = 28.3°, θmin = 2.8° |
16366 measured reflections | h = −12→13 |
6721 independent reflections | k = −13→14 |
3813 reflections with I > 2σ(I) | l = −18→19 |
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(Fo2) + (0.0619P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.133 | (Δ/σ)max = 0.009 |
S = 0.97 | Δρmax = 0.64 e Å−3 |
6721 reflections | Δρmin = −0.55 e Å−3 |
377 parameters |
NH4+·C24H32O8·PF6− | γ = 89.670 (1)° |
Mr = 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)° |
KappaCCD diffractometer | 3813 reflections with I > 2σ(I) |
16366 measured reflections | Rint = 0.044 |
6721 independent reflections |
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 | Δρmax = 0.64 e Å−3 |
6721 reflections | Δρmin = −0.55 e Å−3 |
377 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
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)* |
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) |
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 |
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− |
Mr | 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 |
Rint | 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 |
Δρmax, Δρmin (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).
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) |
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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.