Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805041814/kp6073sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805041814/kp6073Isup2.hkl |
CCDC reference: 296599
The title compound was prepared in 43% yield by the one-pot reaction of diphenylcyclopropenone with Meerwein reagent followed by diethylamine in dichloromethane at room temperature. Single crystals of (I) were obtained by slow cooling of a solution in dichloromethane.
H atoms were treated in a riding mode (C—H = 0.93–0.97 Å). Three free variables for Uiso(H) were refined according to the procedure given in SHELXL97 (Sheldrick, 1997).
Data collection: DARCH Package (Burevestnik, 1991); cell refinement: DARCH Package; data reduction: DARCH Package; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia,1997); software used to prepare material for publication: SHELXL97.
Fig. 1. The constituent ions of (I), showing the atom numbering and displacement ellipsoids drawn at the 50% probability level. | |
Fig. 2. The crystal packing, viewed along the a axis. |
C19H20N+·BF4− | F(000) = 728 |
Mr = 349.17 | Dx = 1.288 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -P 2ybc | Cell parameters from 30 reflections |
a = 14.216 (3) Å | θ = 5–15° |
b = 8.004 (2) Å | µ = 0.10 mm−1 |
c = 18.501 (1) Å | T = 293 K |
β = 121.19 (3)° | Tabular, colourless |
V = 1800.9 (8) Å3 | 0.50 × 0.34 × 0.08 mm |
Z = 4 |
DARCH-1 diffractometer | 2076 reflections with I > 2σ(I) |
Radiation source: BSW x-ray tube | Rint = 0.000 |
Graphite monochromator | θmax = 27.5°, θmin = 1.7° |
w–2θ scan | h = −18→15 |
Absorption correction: part of the refinement model (ΔF) (DIFABS; Walker & Stuart,1983) | k = 0→10 |
Tmin = 0.979, Tmax = 0.997 | l = 0→23 |
4116 measured reflections | 3 standard reflections every 100 reflections |
4116 independent reflections | intensity decay: 2.5% |
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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.121 | H-atom parameters constrained |
S = 0.81 | w = 1/[σ2(Fo2) + (0.0553P)2] where P = (Fo2 + 2Fc2)/3 |
4116 reflections | (Δ/σ)max < 0.001 |
231 parameters | Δρmax = 0.11 e Å−3 |
0 restraints | Δρmin = −0.13 e Å−3 |
C19H20N+·BF4− | V = 1800.9 (8) Å3 |
Mr = 349.17 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 14.216 (3) Å | µ = 0.10 mm−1 |
b = 8.004 (2) Å | T = 293 K |
c = 18.501 (1) Å | 0.50 × 0.34 × 0.08 mm |
β = 121.19 (3)° |
DARCH-1 diffractometer | 2076 reflections with I > 2σ(I) |
Absorption correction: part of the refinement model (ΔF) (DIFABS; Walker & Stuart,1983) | Rint = 0.000 |
Tmin = 0.979, Tmax = 0.997 | 3 standard reflections every 100 reflections |
4116 measured reflections | intensity decay: 2.5% |
4116 independent reflections |
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.121 | H-atom parameters constrained |
S = 0.81 | Δρmax = 0.11 e Å−3 |
4116 reflections | Δρmin = −0.13 e Å−3 |
231 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 | ||
N1 | 0.30027 (10) | −0.01960 (16) | 0.09064 (8) | 0.0956 (3) | |
F1 | 0.29763 (11) | 0.42283 (19) | 0.10553 (8) | 0.1647 (5) | |
F2 | 0.23338 (12) | 0.58715 (16) | 0.16939 (9) | 0.1581 (5) | |
F3 | 0.15700 (11) | 0.34008 (18) | 0.11690 (9) | 0.1723 (6) | |
F4 | 0.32390 (12) | 0.35936 (18) | 0.23299 (9) | 0.1663 (5) | |
B1 | 0.2528 (2) | 0.4276 (3) | 0.15461 (18) | 0.1312 (7) | |
C1 | 0.38796 (12) | 0.15154 (17) | 0.02016 (9) | 0.0902 (4) | |
C2 | 0.27902 (12) | 0.17673 (18) | −0.02842 (9) | 0.0910 (4) | |
C3 | 0.31844 (12) | 0.07670 (18) | 0.04246 (9) | 0.0906 (4) | |
C4 | 0.39081 (14) | −0.1018 (2) | 0.16554 (10) | 0.1054 (5) | |
H4A | 0.4552 | −0.1043 | 0.1603 | 0.156 (4)* | |
H4B | 0.3702 | −0.2163 | 0.1677 | 0.156 (4)* | |
C5 | 0.41936 (16) | −0.0166 (3) | 0.24561 (11) | 0.1329 (6) | |
H5A | 0.4390 | 0.0974 | 0.2437 | 0.170 (3)* | |
H5B | 0.4803 | −0.0727 | 0.2922 | 0.170 (3)* | |
H5C | 0.3572 | −0.0192 | 0.2528 | 0.170 (3)* | |
C6 | 0.18597 (13) | −0.0468 (2) | 0.07090 (11) | 0.1075 (5) | |
H6A | 0.1884 | −0.0962 | 0.1197 | 0.156 (4)* | |
H6B | 0.1494 | 0.0605 | 0.0603 | 0.156 (4)* | |
C7 | 0.12173 (14) | −0.1547 (3) | −0.00214 (12) | 0.1311 (7) | |
H7A | 0.1124 | −0.1012 | −0.0519 | 0.170 (3)* | |
H7B | 0.0510 | −0.1750 | −0.0090 | 0.170 (3)* | |
H7C | 0.1595 | −0.2589 | 0.0064 | 0.170 (3)* | |
C8 | 0.49724 (12) | 0.19413 (17) | 0.03963 (9) | 0.0884 (4) | |
C9 | 0.58897 (13) | 0.1518 (2) | 0.11714 (10) | 0.1013 (4) | |
H9 | 0.5807 | 0.0869 | 0.1552 | 0.144 (2)* | |
C10 | 0.69187 (14) | 0.2058 (2) | 0.13773 (12) | 0.1121 (5) | |
H10 | 0.7528 | 0.1788 | 0.1900 | 0.144 (2)* | |
C11 | 0.70464 (15) | 0.2987 (2) | 0.08153 (13) | 0.1119 (5) | |
H11 | 0.7744 | 0.3349 | 0.0959 | 0.144 (2)* | |
C12 | 0.61567 (17) | 0.3394 (2) | 0.00420 (13) | 0.1137 (5) | |
H12 | 0.6250 | 0.4015 | −0.0341 | 0.144 (2)* | |
C13 | 0.51191 (14) | 0.2872 (2) | −0.01647 (11) | 0.1025 (4) | |
H13 | 0.4514 | 0.3153 | −0.0688 | 0.144 (2)* | |
C14 | 0.18897 (11) | 0.26034 (19) | −0.10059 (9) | 0.0895 (4) | |
C15 | 0.19179 (13) | 0.2839 (2) | −0.17372 (9) | 0.0998 (4) | |
H15 | 0.2515 | 0.2459 | −0.1767 | 0.144 (2)* | |
C16 | 0.10669 (15) | 0.3629 (2) | −0.24119 (11) | 0.1141 (5) | |
H16 | 0.1077 | 0.3764 | −0.2907 | 0.144 (2)* | |
C17 | 0.02026 (15) | 0.4222 (2) | −0.23651 (11) | 0.1211 (6) | |
H17 | −0.0369 | 0.4768 | −0.2829 | 0.144 (2)* | |
C18 | 0.01606 (14) | 0.4031 (2) | −0.16545 (12) | 0.1192 (6) | |
H18 | −0.0428 | 0.4462 | −0.1628 | 0.144 (2)* | |
C19 | 0.09981 (13) | 0.3190 (2) | −0.09676 (10) | 0.1049 (5) | |
H19 | 0.0963 | 0.3021 | −0.0485 | 0.144 (2)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0873 (7) | 0.1041 (8) | 0.0976 (8) | −0.0010 (6) | 0.0494 (6) | 0.0060 (6) |
F1 | 0.1708 (11) | 0.2200 (14) | 0.1524 (10) | −0.0298 (10) | 0.1184 (9) | −0.0280 (9) |
F2 | 0.1905 (12) | 0.1177 (8) | 0.1863 (12) | −0.0036 (8) | 0.1117 (10) | −0.0107 (8) |
F3 | 0.1585 (11) | 0.1870 (12) | 0.1892 (13) | −0.0661 (9) | 0.1026 (10) | −0.0508 (10) |
F4 | 0.1741 (11) | 0.1873 (12) | 0.1388 (10) | 0.0247 (9) | 0.0820 (9) | 0.0215 (9) |
B1 | 0.1379 (19) | 0.1298 (19) | 0.1359 (19) | −0.0120 (16) | 0.0780 (17) | −0.0004 (15) |
C1 | 0.0983 (10) | 0.0870 (8) | 0.0908 (9) | −0.0028 (7) | 0.0528 (8) | −0.0039 (7) |
C2 | 0.0899 (9) | 0.0954 (9) | 0.0923 (9) | −0.0054 (7) | 0.0505 (8) | −0.0089 (7) |
C3 | 0.0909 (9) | 0.0934 (9) | 0.0901 (9) | −0.0009 (7) | 0.0488 (7) | 0.0002 (7) |
C4 | 0.1013 (10) | 0.1062 (11) | 0.1076 (11) | 0.0026 (8) | 0.0534 (9) | 0.0159 (9) |
C5 | 0.1291 (15) | 0.1427 (15) | 0.1110 (13) | 0.0035 (12) | 0.0509 (11) | 0.0077 (12) |
C6 | 0.0964 (10) | 0.1135 (12) | 0.1198 (12) | −0.0030 (9) | 0.0611 (9) | 0.0042 (10) |
C7 | 0.0925 (11) | 0.1751 (19) | 0.1237 (14) | −0.0114 (11) | 0.0547 (10) | −0.0070 (13) |
C8 | 0.0923 (9) | 0.0832 (8) | 0.0955 (9) | −0.0022 (7) | 0.0527 (8) | −0.0048 (7) |
C9 | 0.0948 (10) | 0.1100 (11) | 0.0989 (10) | −0.0041 (8) | 0.0501 (8) | 0.0004 (8) |
C10 | 0.0918 (10) | 0.1287 (13) | 0.1088 (11) | −0.0003 (9) | 0.0470 (9) | −0.0045 (10) |
C11 | 0.0996 (11) | 0.1136 (12) | 0.1355 (15) | −0.0104 (9) | 0.0699 (11) | −0.0147 (11) |
C12 | 0.1349 (15) | 0.1004 (11) | 0.1356 (14) | −0.0105 (10) | 0.0911 (13) | −0.0017 (10) |
C13 | 0.1019 (10) | 0.1087 (10) | 0.1026 (10) | 0.0021 (8) | 0.0570 (9) | 0.0018 (8) |
C14 | 0.0808 (8) | 0.1007 (9) | 0.0835 (8) | 0.0011 (7) | 0.0401 (7) | 0.0013 (7) |
C15 | 0.0926 (9) | 0.1095 (11) | 0.0957 (10) | 0.0058 (8) | 0.0477 (8) | 0.0013 (8) |
C16 | 0.1145 (12) | 0.1331 (14) | 0.0909 (10) | 0.0092 (10) | 0.0505 (10) | 0.0074 (9) |
C17 | 0.1073 (12) | 0.1378 (15) | 0.0960 (11) | 0.0217 (11) | 0.0369 (9) | 0.0171 (10) |
C18 | 0.0968 (11) | 0.1390 (14) | 0.1181 (13) | 0.0242 (10) | 0.0531 (10) | 0.0061 (11) |
C19 | 0.0997 (10) | 0.1253 (12) | 0.0941 (10) | 0.0051 (9) | 0.0533 (9) | 0.0011 (9) |
N1—C3 | 1.3014 (18) | C7—H7B | 0.9600 |
N1—C4 | 1.470 (2) | C7—H7C | 0.9600 |
N1—C6 | 1.4855 (19) | C8—C13 | 1.379 (2) |
F1—B1 | 1.354 (3) | C8—C9 | 1.391 (2) |
F2—B1 | 1.364 (3) | C9—C10 | 1.376 (2) |
F3—F3 | 0.000 (3) | C9—H9 | 0.9300 |
F3—B1 | 1.359 (3) | C10—C11 | 1.365 (2) |
F4—B1 | 1.380 (3) | C10—H10 | 0.9300 |
B1—F3 | 1.359 (3) | C11—C12 | 1.370 (3) |
C1—C2 | 1.344 (2) | C11—H11 | 0.9300 |
C1—C3 | 1.388 (2) | C12—C13 | 1.383 (2) |
C1—C8 | 1.442 (2) | C12—H12 | 0.9300 |
C2—C3 | 1.383 (2) | C13—H13 | 0.9300 |
C2—C14 | 1.449 (2) | C14—C15 | 1.3870 (19) |
C4—C5 | 1.484 (2) | C14—C19 | 1.388 (2) |
C4—H4A | 0.9700 | C15—C16 | 1.363 (2) |
C4—H4B | 0.9700 | C15—H15 | 0.9300 |
C5—H5A | 0.9600 | C16—C17 | 1.361 (3) |
C5—H5B | 0.9600 | C16—H16 | 0.9300 |
C5—H5C | 0.9600 | C17—C18 | 1.355 (2) |
C6—C7 | 1.459 (2) | C17—H17 | 0.9300 |
C6—H6A | 0.9700 | C18—C19 | 1.385 (2) |
C6—H6B | 0.9700 | C18—H18 | 0.9300 |
C7—H7A | 0.9600 | C19—H19 | 0.9300 |
C3—N1—C4 | 121.53 (13) | C6—C7—H7B | 109.5 |
C3—N1—C6 | 119.89 (13) | H7A—C7—H7B | 109.5 |
C4—N1—C6 | 118.57 (13) | C6—C7—H7C | 109.5 |
F3—F3—B1 | 0 (10) | H7A—C7—H7C | 109.5 |
F1—B1—F3 | 109.6 (2) | H7B—C7—H7C | 109.5 |
F1—B1—F3 | 109.6 (2) | C13—C8—C9 | 118.76 (14) |
F3—B1—F3 | 0.00 (16) | C13—C8—C1 | 120.22 (14) |
F1—B1—F2 | 112.0 (2) | C9—C8—C1 | 120.90 (14) |
F3—B1—F2 | 109.4 (2) | C10—C9—C8 | 120.25 (16) |
F3—B1—F2 | 109.4 (2) | C10—C9—H9 | 119.9 |
F1—B1—F4 | 110.5 (2) | C8—C9—H9 | 119.9 |
F3—B1—F4 | 109.2 (2) | C11—C10—C9 | 120.11 (17) |
F3—B1—F4 | 109.2 (2) | C11—C10—H10 | 119.9 |
F2—B1—F4 | 105.9 (2) | C9—C10—H10 | 119.9 |
C2—C1—C3 | 60.82 (11) | C10—C11—C12 | 120.64 (17) |
C2—C1—C8 | 148.32 (14) | C10—C11—H11 | 119.7 |
C3—C1—C8 | 150.25 (14) | C12—C11—H11 | 119.7 |
C1—C2—C3 | 61.20 (11) | C11—C12—C13 | 119.52 (17) |
C1—C2—C14 | 148.01 (14) | C11—C12—H12 | 120.2 |
C3—C2—C14 | 150.67 (14) | C13—C12—H12 | 120.2 |
N1—C3—C2 | 149.92 (15) | C8—C13—C12 | 120.71 (16) |
N1—C3—C1 | 152.04 (15) | C8—C13—H13 | 119.6 |
C2—C3—C1 | 57.99 (10) | C12—C13—H13 | 119.6 |
N1—C4—C5 | 112.87 (15) | C15—C14—C19 | 119.50 (14) |
N1—C4—H4A | 109.0 | C15—C14—C2 | 120.24 (13) |
C5—C4—H4A | 109.0 | C19—C14—C2 | 120.26 (13) |
N1—C4—H4B | 109.0 | C16—C15—C14 | 119.74 (15) |
C5—C4—H4B | 109.0 | C16—C15—H15 | 120.1 |
H4A—C4—H4B | 107.8 | C14—C15—H15 | 120.1 |
C4—C5—H5A | 109.5 | C17—C16—C15 | 120.39 (17) |
C4—C5—H5B | 109.5 | C17—C16—H16 | 119.8 |
H5A—C5—H5B | 109.5 | C15—C16—H16 | 119.8 |
C4—C5—H5C | 109.5 | C18—C17—C16 | 121.13 (17) |
H5A—C5—H5C | 109.5 | C18—C17—H17 | 119.4 |
H5B—C5—H5C | 109.5 | C16—C17—H17 | 119.4 |
C7—C6—N1 | 113.26 (14) | C17—C18—C19 | 119.76 (17) |
C7—C6—H6A | 108.9 | C17—C18—H18 | 120.1 |
N1—C6—H6A | 108.9 | C19—C18—H18 | 120.1 |
C7—C6—H6B | 108.9 | C18—C19—C14 | 119.44 (15) |
N1—C6—H6B | 108.9 | C18—C19—H19 | 120.3 |
H6A—C6—H6B | 107.7 | C14—C19—H19 | 120.3 |
C6—C7—H7A | 109.5 | ||
F3—F3—B1—F1 | 0.00 (5) | C2—C1—C8—C9 | 162.5 (2) |
F3—F3—B1—F2 | 0.00 (3) | C3—C1—C8—C9 | −2.0 (3) |
F3—F3—B1—F4 | 0.00 (2) | C13—C8—C9—C10 | 1.5 (2) |
C8—C1—C2—C3 | −171.3 (3) | C1—C8—C9—C10 | −174.36 (14) |
C3—C1—C2—C14 | 176.1 (3) | C8—C9—C10—C11 | −1.1 (3) |
C8—C1—C2—C14 | 4.8 (4) | C9—C10—C11—C12 | −0.1 (3) |
C4—N1—C3—C2 | 177.9 (2) | C10—C11—C12—C13 | 0.8 (3) |
C6—N1—C3—C2 | −2.8 (4) | C9—C8—C13—C12 | −0.7 (2) |
C4—N1—C3—C1 | 2.5 (4) | C1—C8—C13—C12 | 175.15 (14) |
C6—N1—C3—C1 | −178.2 (3) | C11—C12—C13—C8 | −0.4 (3) |
C1—C2—C3—N1 | −177.5 (3) | C1—C2—C14—C15 | 38.2 (3) |
C14—C2—C3—N1 | 6.8 (5) | C3—C2—C14—C15 | −148.8 (2) |
C14—C2—C3—C1 | −175.8 (3) | C1—C2—C14—C19 | −141.1 (2) |
C2—C1—C3—N1 | 177.3 (3) | C3—C2—C14—C19 | 31.9 (3) |
C8—C1—C3—N1 | −12.0 (5) | C19—C14—C15—C16 | −0.6 (2) |
C8—C1—C3—C2 | 170.7 (3) | C2—C14—C15—C16 | −179.92 (15) |
C3—N1—C4—C5 | 101.73 (18) | C14—C15—C16—C17 | 1.5 (3) |
C6—N1—C4—C5 | −77.56 (19) | C15—C16—C17—C18 | −0.6 (3) |
C3—N1—C6—C7 | 73.2 (2) | C16—C17—C18—C19 | −1.3 (3) |
C4—N1—C6—C7 | −107.45 (18) | C17—C18—C19—C14 | 2.2 (3) |
C2—C1—C8—C13 | −13.4 (3) | C15—C14—C19—C18 | −1.2 (2) |
C3—C1—C8—C13 | −177.8 (2) | C2—C14—C19—C18 | 178.08 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4B···F2i | 0.97 | 2.51 | 3.373 (2) | 148 |
C6—H6B···F3 | 0.97 | 2.45 | 3.293 (2) | 145 |
C12—H12···F1ii | 0.93 | 2.54 | 3.443 (2) | 165 |
C15—H15···F4iii | 0.93 | 2.52 | 3.343 (2) | 148 |
Symmetry codes: (i) x, y−1, z; (ii) −x+1, −y+1, −z; (iii) x, −y+1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C19H20N+·BF4− |
Mr | 349.17 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 14.216 (3), 8.004 (2), 18.501 (1) |
β (°) | 121.19 (3) |
V (Å3) | 1800.9 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.50 × 0.34 × 0.08 |
Data collection | |
Diffractometer | DARCH-1 diffractometer |
Absorption correction | Part of the refinement model (ΔF) (DIFABS; Walker & Stuart,1983) |
Tmin, Tmax | 0.979, 0.997 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4116, 4116, 2076 |
Rint | 0.000 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.121, 0.81 |
No. of reflections | 4116 |
No. of parameters | 231 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.11, −0.13 |
Computer programs: DARCH Package (Burevestnik, 1991), DARCH Package, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia,1997), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4B···F2i | 0.97 | 2.51 | 3.373 (2) | 148 |
C6—H6B···F3 | 0.97 | 2.45 | 3.293 (2) | 145 |
C12—H12···F1ii | 0.93 | 2.54 | 3.443 (2) | 165 |
C15—H15···F4iii | 0.93 | 2.52 | 3.343 (2) | 148 |
Symmetry codes: (i) x, y−1, z; (ii) −x+1, −y+1, −z; (iii) x, −y+1/2, z−1/2. |
Small unsaturated carbon fragments are important in fields ranging from organometallic chemistry (Bruce, 1998) to materials science (Dresselhaus et al., 1996) and astrophysics (Weltner & Van Zee, 1989). The cyclopropenylium ion is the another Huckel aromatic cation and would be a candidate for the cationic component of such unusual hydrocarbons (Kitagawa et al., 2001). Although numerous derivatives of the cyclopropenylium ion have been prepared over the past decades (Komatsu & Yoshida, 1996), there are very few cyclopropenylium ions that are conjugated with amino moieties (Yoshida et al., 1985; Matsumoto et al., 2002, 2003). Recently, we have synthesized and solved the structure of the title compound, (I).
The asymmetric unit of (I) consists of an aminodiphenylcyclopropenylium cation and a tetrafluoroborate anion (Fig. 1). The F atoms of the anion revealed high displacement parameters. The cation contains a planar cyclopropene ring. The plane of cyclopropene ring is inclined to the C8–C13 and C14–C19 phenyl rings at angles of 12.14 (13) and 35.78 (14)°, respectively. The dihedral angle between two phenyl rings is 45.23 (8)°. The N atom of the diethylamine group is displaced by 0.029 (1) Å from the plane defined by atoms C1–C3. In the crystal structure, each cation is linked by four anions via C—H···F hydrogen bonds (Table 1).