organic compounds
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N,N,2,4,6-Pentamethylanilinium hexafluorophosphate–1,4,7,10,13,16-hexaoxacyclooctadecane (2/1)
aDepartment of Applied Chemistry, Nanjing College of Chemical Technology, Nanjing 210048, People's Republic of China
*Correspondence e-mail: 75104209@qq.com
In the title compound, 2C11H18N+·2PF6−·C12H24O6, the 18-crown-6 molecule has crystallographically imposed inversion symmetry. In the crystal, it interacts with the cation through weak C—H⋯O hydrogen bonds. The cations and anions are further linked via N—H⋯F and C—H⋯F hydrogen bonds, leading to a sandwich structure .
CCDC reference: 976922
Related literature
For background to the development of ferroelectric pure organic or inorganic compounds, see: Haertling (1999); Homes et al. (2001). For the structure of a related compound, see: Zhang (2013).
Experimental
Crystal data
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Data collection: CrystalClear (Rigaku, 2005); cell CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supporting information
CCDC reference: 976922
https://doi.org/10.1107/S1600536813033734/rz5098sup1.cif
contains datablocks I, New_Global_Publ_Block. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813033734/rz5098Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536813033734/rz5098Isup3.cml
A mixture of N,N,2,4,6-pentamethylbenzenamine (1.36 g, 10 mmol), hexafluorophosphoric acid(1.90 g, 10 mmol) and 1,4,7,10,13,16-hexaoxacyclooctadecane (2.64, 10 mmol) in methanol(30 ml) was stirred until clear. After several days, the title compound was formed and recrystallized from a methanol solution to afford colourless prismatic crystals suitable for X-ray analysis.
H atoms were positioned geometrically and refined using a riding model, with C—H = 0.97 Å, N—H = 0.91 Å, and Uiso(H) = 1.2 Ueq(C, N) or 1.5 Ueq(C) for methyl H atoms
As a continuation of our studies on the development of novel ferroelectric pure organic or inorganic compounds (Haertling et al., 1999; Homes et al., 2001), we investigated the physical properties of the title compound. Recently the
of the strictly related compound N,N,2,4,6-pentamethylanilinium hexafluorophosphate was reported by our group (Zhang, 2013). The of the title compound as a function of the temperature indicates that the permittivity is basically temperature-independent (dielectric constant equaling to 4.1 to 6.1), suggesting that this compound should be not a real or there may be no distinct occurring within the measured temperature range. Similarly, below the melting point (180°C) of the compound, the as a function of temperature also goes smoothly, and there is no dielectric anomaly observed (dielectric constant equaling to 4.1 to 6.1). Herein, we report the synthesis and of the title compound.The
of the title compound (Fig. 1) consists of one N,N,2,4,6-pentamethylanilinium cation, one hexafluorophosphate anion and one half of a 1,4,7,10,13,16-hexaoxacyclooctadecane molecule. Bond distances and bond angles are not unusual. In the (Fig. 2), the 18-crown-6 molecule interacts with the cation through weak C—H···O hydrogen bonds (Table 1). Cation and anion are further linked via N—H···F and C—H···F hydrogen bonds. Dipole–dipole and van der Waals interactions are effective in stabilizing the molecular packing.For background to the development of ferroelectric pure organic or inorganic compounds, see: Haertling (1999); Homes et al. (2001). For the structure of a related compound, see: Zhang (2013).
Data collection: CrystalClear (Rigaku, 2005); cell
CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).Fig. 1. Perspective view of the title compound, showing the displacement ellipsoids drawn at the 30% probability level. Atoms with the suffix A are generated by symmetry code -x, 2-y, 1-z. | |
Fig. 2. Crystal packing of the title compound viewed along the b axis, showing the hydrogen bonding network (dashed lines). |
2C11H18N+·2PF6−·C12H24O6 | F(000) = 928 |
Mr = 882.78 | Dx = 1.334 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3858 reflections |
a = 8.9122 (18) Å | θ = 2.6–25.0° |
b = 16.775 (3) Å | µ = 0.19 mm−1 |
c = 15.136 (3) Å | T = 293 K |
β = 103.71 (3)° | Prism, colourless |
V = 2198.4 (8) Å3 | 0.40 × 0.30 × 0.20 mm |
Z = 2 |
Rigaku Mercury2 (2x2 bin mode) diffractometer | 3858 independent reflections |
Radiation source: fine-focus sealed tube | 2524 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.053 |
Detector resolution: 13.6612 pixels mm-1 | θmax = 25.0°, θmin = 3.0° |
CCD_Profile_fitting scans | h = −10→10 |
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) | k = −19→19 |
Tmin = 0.832, Tmax = 1.000 | l = −17→17 |
18170 measured reflections |
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)] = 0.083 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.195 | H-atom parameters constrained |
S = 1.20 | w = 1/[σ2(Fo2) + (0.0528P)2 + 2.P] where P = (Fo2 + 2Fc2)/3 |
3858 reflections | (Δ/σ)max = 0.003 |
253 parameters | Δρmax = 0.49 e Å−3 |
0 restraints | Δρmin = −0.30 e Å−3 |
2C11H18N+·2PF6−·C12H24O6 | V = 2198.4 (8) Å3 |
Mr = 882.78 | Z = 2 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.9122 (18) Å | µ = 0.19 mm−1 |
b = 16.775 (3) Å | T = 293 K |
c = 15.136 (3) Å | 0.40 × 0.30 × 0.20 mm |
β = 103.71 (3)° |
Rigaku Mercury2 (2x2 bin mode) diffractometer | 3858 independent reflections |
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) | 2524 reflections with I > 2σ(I) |
Tmin = 0.832, Tmax = 1.000 | Rint = 0.053 |
18170 measured reflections |
R[F2 > 2σ(F2)] = 0.083 | 0 restraints |
wR(F2) = 0.195 | H-atom parameters constrained |
S = 1.20 | Δρmax = 0.49 e Å−3 |
3858 reflections | Δρmin = −0.30 e Å−3 |
253 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. |
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 | ||
P1 | 0.47256 (14) | 0.24011 (8) | 0.74636 (8) | 0.0722 (4) | |
F6 | 0.4805 (5) | 0.2762 (2) | 0.6529 (2) | 0.1280 (12) | |
F5 | 0.3159 (4) | 0.2840 (2) | 0.7412 (3) | 0.1289 (12) | |
F4 | 0.3770 (4) | 0.16651 (18) | 0.6942 (2) | 0.1268 (12) | |
F3 | 0.4597 (5) | 0.2030 (2) | 0.8388 (2) | 0.1461 (15) | |
F2 | 0.5602 (5) | 0.3133 (2) | 0.7981 (3) | 0.1507 (15) | |
F1 | 0.6268 (5) | 0.1971 (3) | 0.7510 (3) | 0.1725 (19) | |
O3 | 0.2823 (3) | 1.00490 (16) | 0.45178 (17) | 0.0589 (7) | |
O2 | 0.1340 (3) | 0.85340 (16) | 0.45499 (17) | 0.0612 (7) | |
O1 | −0.1059 (3) | 0.85014 (16) | 0.55077 (17) | 0.0609 (7) | |
C6 | 0.2987 (5) | 1.0742 (3) | 0.4023 (3) | 0.0651 (11) | |
H6A | 0.2276 | 1.0722 | 0.3429 | 0.078* | |
H6B | 0.4029 | 1.0771 | 0.3936 | 0.078* | |
C4 | 0.2945 (5) | 0.8633 (3) | 0.4624 (3) | 0.0673 (11) | |
H4A | 0.3358 | 0.8166 | 0.4386 | 0.081* | |
H4B | 0.3480 | 0.8696 | 0.5257 | 0.081* | |
C5 | 0.3191 (5) | 0.9355 (3) | 0.4095 (3) | 0.0647 (11) | |
H5A | 0.4261 | 0.9378 | 0.4056 | 0.078* | |
H5B | 0.2548 | 0.9321 | 0.3482 | 0.078* | |
C2 | −0.0682 (5) | 0.7856 (2) | 0.5001 (3) | 0.0616 (11) | |
H2A | −0.1249 | 0.7899 | 0.4371 | 0.074* | |
H2B | −0.0961 | 0.7357 | 0.5243 | 0.074* | |
C3 | 0.1010 (5) | 0.7875 (2) | 0.5061 (3) | 0.0630 (11) | |
H3A | 0.1573 | 0.7927 | 0.5691 | 0.076* | |
H3B | 0.1329 | 0.7384 | 0.4821 | 0.076* | |
C1 | −0.2661 (5) | 0.8535 (3) | 0.5475 (3) | 0.0664 (11) | |
H1A | −0.2971 | 0.8060 | 0.5751 | 0.080* | |
H1B | −0.3247 | 0.8560 | 0.4848 | 0.080* | |
C7 | 0.0742 (4) | 0.0080 (2) | 0.7882 (2) | 0.0501 (9) | |
N1 | 0.1899 (4) | 0.0220 (2) | 0.7330 (2) | 0.0679 (10) | |
H1C | 0.1970 | 0.0761 | 0.7327 | 0.081* | |
C9 | −0.1049 (5) | 0.0657 (3) | 0.8628 (3) | 0.0647 (11) | |
H9A | −0.1532 | 0.1104 | 0.8797 | 0.078* | |
C12 | 0.0381 (5) | −0.0678 (2) | 0.8125 (3) | 0.0616 (11) | |
C11 | −0.0714 (6) | −0.0732 (3) | 0.8639 (3) | 0.0726 (13) | |
H11A | −0.0971 | −0.1235 | 0.8816 | 0.087* | |
C8 | 0.0030 (4) | 0.0760 (2) | 0.8112 (2) | 0.0537 (10) | |
C10 | −0.1433 (5) | −0.0085 (3) | 0.8899 (3) | 0.0675 (12) | |
C13 | 0.0349 (6) | 0.1585 (2) | 0.7817 (3) | 0.0774 (13) | |
H13A | −0.0270 | 0.1963 | 0.8049 | 0.116* | |
H13B | 0.0099 | 0.1611 | 0.7164 | 0.116* | |
H13C | 0.1422 | 0.1709 | 0.8048 | 0.116* | |
C16 | 0.1342 (6) | 0.0025 (3) | 0.6344 (3) | 0.0709 (12) | |
H16A | 0.2140 | 0.0142 | 0.6035 | 0.106* | |
H16B | 0.0443 | 0.0338 | 0.6087 | 0.106* | |
H16C | 0.1085 | −0.0531 | 0.6277 | 0.106* | |
C17 | 0.3506 (5) | −0.0026 (3) | 0.7753 (4) | 0.0873 (15) | |
H17A | 0.3774 | 0.0142 | 0.8377 | 0.131* | |
H17B | 0.4196 | 0.0217 | 0.7433 | 0.131* | |
H17C | 0.3588 | −0.0595 | 0.7724 | 0.131* | |
C15 | 0.1046 (7) | −0.1451 (3) | 0.7880 (4) | 0.1037 (18) | |
H15A | 0.0592 | −0.1889 | 0.8131 | 0.156* | |
H15B | 0.2144 | −0.1452 | 0.8123 | 0.156* | |
H15C | 0.0827 | −0.1503 | 0.7230 | 0.156* | |
C14 | −0.2611 (6) | −0.0173 (4) | 0.9466 (3) | 0.109 (2) | |
H14A | −0.2989 | 0.0344 | 0.9579 | 0.164* | |
H14B | −0.2137 | −0.0423 | 1.0034 | 0.164* | |
H14C | −0.3455 | −0.0496 | 0.9144 | 0.164* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.0737 (8) | 0.0786 (9) | 0.0619 (7) | 0.0147 (7) | 0.0115 (6) | −0.0153 (6) |
F6 | 0.166 (3) | 0.134 (3) | 0.090 (2) | −0.004 (2) | 0.044 (2) | 0.010 (2) |
F5 | 0.105 (2) | 0.129 (3) | 0.155 (3) | 0.044 (2) | 0.035 (2) | −0.003 (2) |
F4 | 0.177 (3) | 0.088 (2) | 0.106 (2) | −0.022 (2) | 0.017 (2) | −0.0247 (18) |
F3 | 0.202 (4) | 0.166 (4) | 0.074 (2) | 0.046 (3) | 0.041 (2) | 0.022 (2) |
F2 | 0.155 (3) | 0.151 (3) | 0.140 (3) | −0.030 (3) | 0.023 (2) | −0.065 (3) |
F1 | 0.126 (3) | 0.232 (5) | 0.158 (3) | 0.101 (3) | 0.031 (3) | −0.019 (3) |
O3 | 0.0604 (17) | 0.0714 (18) | 0.0509 (15) | −0.0010 (14) | 0.0253 (13) | −0.0022 (14) |
O2 | 0.0529 (16) | 0.0711 (18) | 0.0599 (16) | 0.0049 (14) | 0.0138 (12) | 0.0084 (14) |
O1 | 0.0557 (17) | 0.0676 (18) | 0.0605 (16) | −0.0109 (14) | 0.0164 (13) | −0.0133 (14) |
C6 | 0.053 (2) | 0.090 (3) | 0.057 (2) | −0.012 (2) | 0.0249 (19) | 0.003 (2) |
C4 | 0.054 (3) | 0.079 (3) | 0.070 (3) | 0.011 (2) | 0.019 (2) | −0.001 (2) |
C5 | 0.050 (2) | 0.092 (3) | 0.058 (2) | 0.004 (2) | 0.0234 (19) | −0.004 (2) |
C2 | 0.076 (3) | 0.054 (2) | 0.054 (2) | −0.009 (2) | 0.013 (2) | 0.0014 (19) |
C3 | 0.075 (3) | 0.055 (2) | 0.056 (2) | 0.007 (2) | 0.011 (2) | −0.003 (2) |
C1 | 0.061 (3) | 0.074 (3) | 0.066 (3) | −0.019 (2) | 0.018 (2) | 0.000 (2) |
C7 | 0.054 (2) | 0.059 (2) | 0.0350 (18) | −0.0008 (19) | 0.0063 (16) | 0.0018 (17) |
N1 | 0.065 (2) | 0.083 (3) | 0.055 (2) | 0.0083 (18) | 0.0140 (17) | 0.0001 (18) |
C9 | 0.067 (3) | 0.078 (3) | 0.046 (2) | 0.014 (2) | 0.006 (2) | −0.008 (2) |
C12 | 0.081 (3) | 0.053 (2) | 0.046 (2) | 0.001 (2) | 0.005 (2) | −0.0007 (19) |
C11 | 0.089 (3) | 0.069 (3) | 0.052 (2) | −0.019 (3) | 0.002 (2) | 0.008 (2) |
C8 | 0.061 (2) | 0.055 (2) | 0.040 (2) | 0.0030 (19) | 0.0023 (18) | −0.0010 (17) |
C10 | 0.052 (2) | 0.105 (4) | 0.040 (2) | −0.010 (3) | 0.0013 (18) | 0.006 (2) |
C13 | 0.110 (4) | 0.049 (3) | 0.075 (3) | 0.005 (2) | 0.026 (3) | 0.001 (2) |
C16 | 0.087 (3) | 0.085 (3) | 0.045 (2) | −0.004 (2) | 0.023 (2) | −0.006 (2) |
C17 | 0.067 (3) | 0.090 (4) | 0.100 (4) | 0.011 (3) | 0.010 (3) | 0.010 (3) |
C15 | 0.164 (6) | 0.057 (3) | 0.091 (4) | 0.021 (3) | 0.032 (4) | 0.001 (3) |
C14 | 0.073 (3) | 0.187 (6) | 0.070 (3) | −0.025 (4) | 0.024 (3) | 0.011 (3) |
P1—F1 | 1.539 (3) | C7—C8 | 1.390 (5) |
P1—F6 | 1.556 (3) | C7—N1 | 1.492 (5) |
P1—F3 | 1.560 (3) | N1—C17 | 1.482 (5) |
P1—F2 | 1.562 (4) | N1—C16 | 1.493 (5) |
P1—F5 | 1.564 (3) | N1—H1C | 0.9100 |
P1—F4 | 1.598 (3) | C9—C10 | 1.380 (6) |
O3—C5 | 1.404 (5) | C9—C8 | 1.385 (6) |
O3—C6 | 1.409 (5) | C9—H9A | 0.9300 |
O2—C4 | 1.418 (4) | C12—C11 | 1.389 (6) |
O2—C3 | 1.419 (4) | C12—C15 | 1.507 (6) |
O1—C2 | 1.412 (4) | C11—C10 | 1.364 (6) |
O1—C1 | 1.418 (4) | C11—H11A | 0.9300 |
C6—C1i | 1.495 (6) | C8—C13 | 1.503 (5) |
C6—H6A | 0.9700 | C10—C14 | 1.512 (6) |
C6—H6B | 0.9700 | C13—H13A | 0.9600 |
C4—C5 | 1.497 (6) | C13—H13B | 0.9600 |
C4—H4A | 0.9700 | C13—H13C | 0.9600 |
C4—H4B | 0.9700 | C16—H16A | 0.9600 |
C5—H5A | 0.9700 | C16—H16B | 0.9600 |
C5—H5B | 0.9700 | C16—H16C | 0.9600 |
C2—C3 | 1.490 (6) | C17—H17A | 0.9600 |
C2—H2A | 0.9700 | C17—H17B | 0.9600 |
C2—H2B | 0.9700 | C17—H17C | 0.9600 |
C3—H3A | 0.9700 | C15—H15A | 0.9600 |
C3—H3B | 0.9700 | C15—H15B | 0.9600 |
C1—C6i | 1.495 (6) | C15—H15C | 0.9600 |
C1—H1A | 0.9700 | C14—H14A | 0.9600 |
C1—H1B | 0.9700 | C14—H14B | 0.9600 |
C7—C12 | 1.382 (5) | C14—H14C | 0.9600 |
F1—P1—F6 | 89.5 (2) | C12—C7—C8 | 122.7 (4) |
F1—P1—F3 | 91.6 (2) | C12—C7—N1 | 122.0 (4) |
F6—P1—F3 | 178.3 (2) | C8—C7—N1 | 115.4 (3) |
F1—P1—F2 | 90.6 (3) | C17—N1—C7 | 116.1 (3) |
F6—P1—F2 | 91.4 (2) | C17—N1—C16 | 115.4 (4) |
F3—P1—F2 | 89.9 (2) | C7—N1—C16 | 114.5 (3) |
F1—P1—F5 | 179.7 (2) | C17—N1—H1C | 102.6 |
F6—P1—F5 | 90.2 (2) | C7—N1—H1C | 102.6 |
F3—P1—F5 | 88.7 (2) | C16—N1—H1C | 102.6 |
F2—P1—F5 | 89.4 (2) | C10—C9—C8 | 122.3 (4) |
F1—P1—F4 | 91.5 (2) | C10—C9—H9A | 118.9 |
F6—P1—F4 | 89.15 (19) | C8—C9—H9A | 118.9 |
F3—P1—F4 | 89.5 (2) | C7—C12—C11 | 116.6 (4) |
F2—P1—F4 | 177.8 (2) | C7—C12—C15 | 126.6 (4) |
F5—P1—F4 | 88.5 (2) | C11—C12—C15 | 116.9 (4) |
C5—O3—C6 | 112.2 (3) | C10—C11—C12 | 123.4 (4) |
C4—O2—C3 | 112.6 (3) | C10—C11—H11A | 118.3 |
C2—O1—C1 | 112.3 (3) | C12—C11—H11A | 118.3 |
O3—C6—C1i | 110.0 (3) | C9—C8—C7 | 117.3 (4) |
O3—C6—H6A | 109.7 | C9—C8—C13 | 119.2 (4) |
C1i—C6—H6A | 109.7 | C7—C8—C13 | 123.5 (4) |
O3—C6—H6B | 109.7 | C11—C10—C9 | 117.7 (4) |
C1i—C6—H6B | 109.7 | C11—C10—C14 | 121.5 (5) |
H6A—C6—H6B | 108.2 | C9—C10—C14 | 120.7 (5) |
O2—C4—C5 | 109.0 (3) | C8—C13—H13A | 109.5 |
O2—C4—H4A | 109.9 | C8—C13—H13B | 109.5 |
C5—C4—H4A | 109.9 | H13A—C13—H13B | 109.5 |
O2—C4—H4B | 109.9 | C8—C13—H13C | 109.5 |
C5—C4—H4B | 109.9 | H13A—C13—H13C | 109.5 |
H4A—C4—H4B | 108.3 | H13B—C13—H13C | 109.5 |
O3—C5—C4 | 110.4 (3) | N1—C16—H16A | 109.5 |
O3—C5—H5A | 109.6 | N1—C16—H16B | 109.5 |
C4—C5—H5A | 109.6 | H16A—C16—H16B | 109.5 |
O3—C5—H5B | 109.6 | N1—C16—H16C | 109.5 |
C4—C5—H5B | 109.6 | H16A—C16—H16C | 109.5 |
H5A—C5—H5B | 108.1 | H16B—C16—H16C | 109.5 |
O1—C2—C3 | 108.6 (3) | N1—C17—H17A | 109.5 |
O1—C2—H2A | 110.0 | N1—C17—H17B | 109.5 |
C3—C2—H2A | 110.0 | H17A—C17—H17B | 109.5 |
O1—C2—H2B | 110.0 | N1—C17—H17C | 109.5 |
C3—C2—H2B | 110.0 | H17A—C17—H17C | 109.5 |
H2A—C2—H2B | 108.4 | H17B—C17—H17C | 109.5 |
O2—C3—C2 | 108.7 (3) | C12—C15—H15A | 109.5 |
O2—C3—H3A | 109.9 | C12—C15—H15B | 109.5 |
C2—C3—H3A | 109.9 | H15A—C15—H15B | 109.5 |
O2—C3—H3B | 109.9 | C12—C15—H15C | 109.5 |
C2—C3—H3B | 109.9 | H15A—C15—H15C | 109.5 |
H3A—C3—H3B | 108.3 | H15B—C15—H15C | 109.5 |
O1—C1—C6i | 109.3 (3) | C10—C14—H14A | 109.5 |
O1—C1—H1A | 109.8 | C10—C14—H14B | 109.5 |
C6i—C1—H1A | 109.8 | H14A—C14—H14B | 109.5 |
O1—C1—H1B | 109.8 | C10—C14—H14C | 109.5 |
C6i—C1—H1B | 109.8 | H14A—C14—H14C | 109.5 |
H1A—C1—H1B | 108.3 | H14B—C14—H14C | 109.5 |
Symmetry code: (i) −x, −y+2, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1C···F4 | 0.91 | 2.38 | 3.077 (5) | 134 |
C16—H16A···O3ii | 0.96 | 2.52 | 3.334 (5) | 143 |
C16—H16B···O2iii | 0.96 | 2.51 | 3.443 (5) | 164 |
C16—H16C···O1ii | 0.96 | 2.57 | 3.381 (5) | 143 |
C17—H17B···F4 | 0.96 | 2.54 | 3.122 (6) | 119 |
Symmetry codes: (ii) x, y−1, z; (iii) −x, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1C···F4 | 0.91 | 2.38 | 3.077 (5) | 133.6 |
C16—H16A···O3i | 0.96 | 2.52 | 3.334 (5) | 143.1 |
C16—H16B···O2ii | 0.96 | 2.51 | 3.443 (5) | 163.6 |
C16—H16C···O1i | 0.96 | 2.57 | 3.381 (5) | 142.8 |
C17—H17B···F4 | 0.96 | 2.54 | 3.122 (6) | 118.9 |
Symmetry codes: (i) x, y−1, z; (ii) −x, −y+1, −z+1. |
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
As a continuation of our studies on the development of novel ferroelectric pure organic or inorganic compounds (Haertling et al., 1999; Homes et al., 2001), we investigated the physical properties of the title compound. Recently the crystal structure of the strictly related compound N,N,2,4,6-pentamethylanilinium hexafluorophosphate was reported by our group (Zhang, 2013). The dielectric constant of the title compound as a function of the temperature indicates that the permittivity is basically temperature-independent (dielectric constant equaling to 4.1 to 6.1), suggesting that this compound should be not a real ferroelectrics or there may be no distinct phase transition occurring within the measured temperature range. Similarly, below the melting point (180°C) of the compound, the dielectric constant as a function of temperature also goes smoothly, and there is no dielectric anomaly observed (dielectric constant equaling to 4.1 to 6.1). Herein, we report the synthesis and crystal structure of the title compound.
The asymmetric unit of the title compound (Fig. 1) consists of one N,N,2,4,6-pentamethylanilinium cation, one hexafluorophosphate anion and one half of a 1,4,7,10,13,16-hexaoxacyclooctadecane molecule. Bond distances and bond angles are not unusual. In the crystal structure (Fig. 2), the 18-crown-6 molecule interacts with the cation through weak C—H···O hydrogen bonds (Table 1). Cation and anion are further linked via N—H···F and C—H···F hydrogen bonds. Dipole–dipole and van der Waals interactions are effective in stabilizing the molecular packing.