The synthesis, characterization and structural analysis of triphenylphosphoniummethylenetrifluoroborate are presented.
Keywords: crystal structure, trifluoroborates, zwitterions, phosphonium
Abstract
The title compound, C19H17BF3P {alternative name: triphenyl[(trifluoroboranyl)methyl]phosphanium}, was formed by the reaction of triphenylphosphine with potassium iodomethyltrifluoroborate. The molecule features a nearly staggered conformation along the P—C bond and a less than staggered conformation along the C—B bond. In the crystal, weak C—H⋯F hydrogen bonds between the meta-phenyl C—H groups and the trifluoroborate B—F groups form chains of R 2 2(16) rings along [100]. These chains are are further stabilized by weak C—H⋯π interactions. A weak intramolecular C—H⋯F hydrogen bond is also observed.
Chemical context
Alkyltriphenylphosphonium (Ph3PRX) salts are widely used as precursors in the preparation of phosphorus ylides for Wittig-type olefination (Julia, 1985 ▸). Such olefination reactions continue to be one of the most important means of alkene generation. Potassium organotrifluoroborates (KRBF3) are common substrates used in Suzuki–Miyaura coupling as stable boronic acid precursors. Additionally, they may be used to produce organodihaloboranes (RBX
2) (Darses & Genet, 2008 ▸). Seyferth & Grim (1961 ▸) showed that reaction of triphenylphosphinemethylene ylide (Ph3PCH2
−) with boron trifluoride diethyletherate (BF3-OEt2) yields triphenyl[(trifluoroboranyl)methyl]phosphonium (Ph3PCH2BF3). We have synthesized Ph3PCH2BF3
via an alternate route, by reacting triphenylphosphine (PPh3) with potassium iodomethyltrifluoroborate (ICH2BF3K) in 45% yield.
There are many examples of zwitterionic organotrifluoroborates containing ammonium moieties, but very few containing phosphonium groups have been reported (see Database survey). Phosphonium trifluoroborates have been shown to enhance the hydrolytic stability of the RBF3 moiety (Wade et al., 2010 ▸.) In this context we synthesized Ph3PCH2BF3 and report herein its crystal structure.
Structural commentary
The molecular structure of the title compound is shown in Fig. 1 ▸. A weak intramolecular C—H⋯F hydrogen bond forms an S(7) ring (Table 1 ▸). The molecule features a nearly anti conformation along the P1—C1 bond [B1—C1—P1—C8 torsion angle = 172.4 (2)°] and a less staggered conformation along the C1—B1 bond [F2—B1—C1—P1 torsion angle = 158.3 (2)°].
Figure 1.
The molecular structure of the title compound, with displacement ellipsoids drawn at the 50% probability level.
Table 1. Hydrogen-bond geometry (Å, °).
Cg1 is the centroid of the C2–C7 ring.
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| C4—H4⋯F1i | 0.95 (3) | 2.44 (2) | 3.293 (4) | 149.7 (17) |
| C12—H12⋯F1ii | 0.96 (3) | 2.37 (3) | 3.084 (3) | 131 (2) |
| C19—H19⋯F1 | 0.97 (2) | 2.43 (2) | 3.263 (3) | 143.9 (18) |
| C11—H11⋯Cg ii | 0.89 (3) | 2.77 (3) | 3.639 (3) | 165 (2) |
Symmetry codes: (i) 
; (ii) 
.
The B-F bond lengths fall within normal ranges for organotrifluoroborate compounds. The methylene C—P bond length [1.787 (4) Å] and the C—B bond length [1.636 (4) Å] also fall within the normal range for similar compounds (Allen et al., 1987 ▸). In terms of the surrounding angles, the B and P atoms appear to be sp3 hybridized. The methylene carbon is predominantly sp3 hybridized, but has a distorted tetrahedral geometry with a P1—C1—B1 angle of 119.7 (2)°.
Supramolecular features
In the crystal, two weak C—H⋯F hydrogen bonds between the meta hydrogen atoms on the triphenylphosphonium rings and the trifluoroborate moiety (Table 1 ▸) fall within the range of distances observed in other triphenylphosphonium trifluoroborates (Wade et al., 2010 ▸) and form chains of 
(16) rings along the [100] axis (Fig. 2 ▸). These chains are further stabilized by herringbone edge-to-face weak C—H⋯π interactions (Fig. 3 ▸).
Figure 2.
Part of the crystal structure, showing weak C—H⋯F hydrogen bonds as dashed lines.
Figure 3.
Part of the crystal structure, showing weak C—H⋯π interactions along [100] as dashed lines. Only the H atoms involved in these interactions are shown.
Database survey
A search of the Cambridge Structural Database (Version 5.37, update February 2017; Groom et al., 2016 ▸) for phosphonium-containing trifluoroborates yielded only five structures: FUYDIN (Wade et al., 2010 ▸), OZOJOD (Gott et al., 2011 ▸), PUXWEL (Piskunov et al., 2010 ▸), ZEKLEI (Li et al., 2012 ▸) and ZEKLOS (Zibo et al., 2012 ▸).
Synthesis and crystallization
Potassium iodomethyltrifluoroborate (1.00 g, 4.04 mmol) and triphenylphosphine (1.11 g, 4.23 mmol) were combined in a pressure flask containing a stir bar under nitrogen, and anhydrous THF (25.0 mL) was added. The flask was sealed and heated to 343 K for 18 h. The reaction was cooled to room temperature and the solvent was removed in vacuo. The residue was washed with Et2O (3 x 10 mL) and the resulting solid was dissolved in a minimal amount of acetone and the product was precipitated with water and collected by filtration, to afford a white solid (0.63 g, 1.82 mmol, 45%.) X-ray quality crystals were grown by slow diffusion of pentane into a solution of the title compound dissolved in dichloromethane.
1H NMR (500 MHz, CDCl3) δ (ppm): 7.66 (m, 9H), 7.56 (m, 6H), 2.07 (br d, 2H, J = 15 Hz). 13C NMR (126 MHz, CDCl3) δ (ppm): 133.7 (d, J = 3 Hz), 133.5 (d, J = 10 Hz), 129.6 (d, J = 12 Hz) 123.2 (d, J = 87 Hz) (C—B not observed). 11B NMR (160 MHz, CDCl3) δ (ppm): 2.49 (q, J = 47 Hz). 19F NMR (470 MHz, CDCl3) δ (ppm): −138.9 (q, J = 37 Hz). FTIR (ATR, cm−1): 3070, 2960, 1587, 1484, 1438, 1146, 1104, 1025, 994, 969, 824, 754, 725, 691, 511, 497.
Refinement details
Crystal data, data collection and structure refinement details are summarized in Table 2 ▸. All H atoms were refined independently with isotropic displacement parameters.
Table 2. Experimental details.
| Crystal data | |
| Chemical formula | C19H17BF3P |
| M r | 344.10 |
| Crystal system, space group | Triclinic, P
|
| Temperature (K) | 173 |
| a, b, c (Å) | 9.514 (2), 9.870 (3), 9.883 (3) |
| α, β, γ (°) | 64.609 (6), 87.539 (7), 86.660 (7) |
| V (Å3) | 836.8 (4) |
| Z | 2 |
| Radiation type | Mo Kα |
| μ (mm−1) | 0.19 |
| Crystal size (mm) | 0.13 × 0.07 × 0.01 |
| Data collection | |
| Diffractometer | Bruker APEXII CCD |
| Absorption correction | Multi-scan (SADABS; Bruker, 2012 ▸) |
| T min, T max | 0.925, 1.000 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 11811, 2953, 2090 |
| R int | 0.061 |
| (sin θ/λ)max (Å−1) | 0.595 |
| Refinement | |
| R[F 2 > 2σ(F 2)], wR(F 2), S | 0.041, 0.094, 1.02 |
| No. of reflections | 2953 |
| No. of parameters | 285 |
| H-atom treatment | All H-atom parameters refined |
| Δρmax, Δρmin (e Å−3) | 0.26, −0.29 |
Supplementary Material
Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989017009884/lh5846sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989017009884/lh5846Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989017009884/lh5846Isup3.cml
CCDC reference: 1560028
Additional supporting information: crystallographic information; 3D view; checkCIF report
supplementary crystallographic information
Crystal data
| C19H17BF3P | Z = 2 |
| Mr = 344.10 | F(000) = 356 |
| Triclinic, P1 | Dx = 1.366 Mg m−3 |
| a = 9.514 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
| b = 9.870 (3) Å | Cell parameters from 2126 reflections |
| c = 9.883 (3) Å | θ = 2.3–23.9° |
| α = 64.609 (6)° | µ = 0.19 mm−1 |
| β = 87.539 (7)° | T = 173 K |
| γ = 86.660 (7)° | Plate, colorless |
| V = 836.8 (4) Å3 | 0.13 × 0.07 × 0.01 mm |
Data collection
| Bruker APEXII CCD diffractometer | 2090 reflections with I > 2σ(I) |
| Radiation source: sealed tube | Rint = 0.061 |
| φ and ω scans | θmax = 25.0°, θmin = 2.2° |
| Absorption correction: multi-scan (SADABS; Bruker, 2012) | h = −11→11 |
| Tmin = 0.925, Tmax = 1.000 | k = −10→11 |
| 11811 measured reflections | l = −11→11 |
| 2953 independent reflections |
Refinement
| Refinement on F2 | 0 restraints |
| Least-squares matrix: full | Hydrogen site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.041 | All H-atom parameters refined |
| wR(F2) = 0.094 | w = 1/[σ2(Fo2) + (0.0458P)2] where P = (Fo2 + 2Fc2)/3 |
| S = 1.02 | (Δ/σ)max < 0.001 |
| 2953 reflections | Δρmax = 0.26 e Å−3 |
| 285 parameters | Δρmin = −0.29 e Å−3 |
Special details
| Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| P1 | 0.88100 (6) | 0.18041 (7) | 0.68950 (7) | 0.01697 (18) | |
| B1 | 0.6884 (3) | 0.2752 (3) | 0.8793 (3) | 0.0230 (7) | |
| F1 | 0.58103 (14) | 0.26765 (16) | 0.79007 (15) | 0.0321 (4) | |
| F2 | 0.66153 (16) | 0.40289 (16) | 0.90564 (16) | 0.0385 (4) | |
| F3 | 0.68558 (16) | 0.14803 (16) | 1.01567 (15) | 0.0381 (4) | |
| C1 | 0.8421 (3) | 0.2870 (3) | 0.7950 (3) | 0.0208 (6) | |
| C2 | 0.7769 (2) | 0.2468 (2) | 0.5241 (2) | 0.0159 (5) | |
| C3 | 0.7246 (3) | 0.3952 (3) | 0.4576 (3) | 0.0244 (6) | |
| C4 | 0.6496 (3) | 0.4457 (3) | 0.3269 (3) | 0.0290 (6) | |
| C5 | 0.6268 (3) | 0.3508 (3) | 0.2611 (3) | 0.0260 (6) | |
| C6 | 0.6785 (3) | 0.2042 (3) | 0.3260 (3) | 0.0270 (6) | |
| C7 | 0.7526 (3) | 0.1511 (3) | 0.4578 (3) | 0.0227 (6) | |
| C8 | 1.0645 (2) | 0.1992 (2) | 0.6332 (2) | 0.0177 (5) | |
| C9 | 1.1081 (3) | 0.2542 (3) | 0.4834 (3) | 0.0208 (6) | |
| C10 | 1.2509 (3) | 0.2685 (3) | 0.4467 (3) | 0.0271 (6) | |
| C11 | 1.3487 (3) | 0.2274 (3) | 0.5571 (3) | 0.0282 (6) | |
| C12 | 1.3064 (3) | 0.1730 (3) | 0.7066 (3) | 0.0249 (6) | |
| C13 | 1.1648 (2) | 0.1596 (3) | 0.7452 (3) | 0.0224 (6) | |
| C14 | 0.8521 (2) | −0.0170 (3) | 0.7952 (2) | 0.0175 (5) | |
| C15 | 0.9617 (3) | −0.1247 (3) | 0.8201 (3) | 0.0221 (6) | |
| C16 | 0.9361 (3) | −0.2760 (3) | 0.8966 (3) | 0.0276 (6) | |
| C17 | 0.8011 (3) | −0.3208 (3) | 0.9478 (3) | 0.0296 (6) | |
| C18 | 0.6919 (3) | −0.2144 (3) | 0.9237 (3) | 0.0293 (6) | |
| C19 | 0.7161 (3) | −0.0636 (3) | 0.8475 (3) | 0.0234 (6) | |
| H1A | 0.860 (3) | 0.389 (3) | 0.727 (3) | 0.034 (8)* | |
| H1B | 0.913 (3) | 0.256 (3) | 0.864 (3) | 0.036 (8)* | |
| H3 | 0.736 (3) | 0.457 (3) | 0.510 (3) | 0.048 (8)* | |
| H4 | 0.616 (2) | 0.547 (3) | 0.282 (2) | 0.024 (7)* | |
| H5 | 0.578 (2) | 0.385 (3) | 0.171 (3) | 0.029 (7)* | |
| H6 | 0.662 (3) | 0.139 (3) | 0.281 (3) | 0.032 (7)* | |
| H7 | 0.785 (2) | 0.043 (3) | 0.508 (2) | 0.022 (6)* | |
| H9 | 1.043 (2) | 0.282 (2) | 0.404 (2) | 0.019 (6)* | |
| H10 | 1.279 (2) | 0.310 (3) | 0.342 (3) | 0.030 (7)* | |
| H11 | 1.441 (3) | 0.233 (3) | 0.535 (3) | 0.028 (7)* | |
| H12 | 1.374 (3) | 0.148 (3) | 0.784 (3) | 0.039 (8)* | |
| H13 | 1.135 (2) | 0.119 (2) | 0.851 (3) | 0.024 (6)* | |
| H15 | 1.055 (2) | −0.099 (2) | 0.789 (2) | 0.020 (6)* | |
| H16 | 1.014 (3) | −0.352 (3) | 0.915 (3) | 0.036 (7)* | |
| H17 | 0.785 (3) | −0.429 (3) | 1.000 (3) | 0.042 (8)* | |
| H18 | 0.603 (3) | −0.246 (3) | 0.958 (3) | 0.032 (7)* | |
| H19 | 0.639 (2) | 0.011 (3) | 0.829 (2) | 0.023 (6)* |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| P1 | 0.0150 (3) | 0.0181 (4) | 0.0176 (3) | −0.0004 (2) | −0.0011 (2) | −0.0073 (3) |
| B1 | 0.0240 (16) | 0.0278 (18) | 0.0209 (15) | 0.0002 (13) | −0.0003 (12) | −0.0141 (13) |
| F1 | 0.0175 (7) | 0.0438 (10) | 0.0395 (9) | 0.0008 (6) | −0.0033 (6) | −0.0220 (8) |
| F2 | 0.0425 (9) | 0.0369 (10) | 0.0466 (10) | −0.0011 (7) | 0.0079 (7) | −0.0287 (8) |
| F3 | 0.0475 (10) | 0.0350 (9) | 0.0237 (8) | 0.0007 (7) | 0.0056 (7) | −0.0058 (7) |
| C1 | 0.0199 (13) | 0.0252 (16) | 0.0203 (13) | −0.0003 (11) | −0.0050 (11) | −0.0123 (12) |
| C2 | 0.0132 (12) | 0.0185 (14) | 0.0163 (12) | −0.0006 (10) | 0.0006 (9) | −0.0078 (10) |
| C3 | 0.0286 (14) | 0.0200 (15) | 0.0252 (13) | −0.0005 (11) | −0.0048 (11) | −0.0100 (12) |
| C4 | 0.0344 (16) | 0.0198 (16) | 0.0270 (14) | 0.0022 (12) | −0.0058 (12) | −0.0044 (12) |
| C5 | 0.0255 (14) | 0.0309 (17) | 0.0167 (13) | −0.0010 (12) | −0.0047 (11) | −0.0051 (12) |
| C6 | 0.0273 (14) | 0.0368 (17) | 0.0250 (14) | −0.0013 (12) | −0.0035 (11) | −0.0205 (13) |
| C7 | 0.0283 (14) | 0.0198 (15) | 0.0220 (13) | 0.0021 (11) | −0.0040 (11) | −0.0108 (12) |
| C8 | 0.0173 (12) | 0.0140 (13) | 0.0212 (12) | −0.0012 (10) | −0.0003 (10) | −0.0069 (10) |
| C9 | 0.0215 (13) | 0.0191 (14) | 0.0224 (13) | −0.0003 (10) | −0.0006 (11) | −0.0093 (11) |
| C10 | 0.0301 (15) | 0.0254 (16) | 0.0269 (15) | −0.0053 (12) | 0.0085 (12) | −0.0124 (12) |
| C11 | 0.0174 (14) | 0.0246 (16) | 0.0433 (17) | −0.0053 (11) | 0.0070 (13) | −0.0153 (13) |
| C12 | 0.0182 (14) | 0.0222 (15) | 0.0332 (15) | −0.0034 (11) | −0.0032 (12) | −0.0102 (12) |
| C13 | 0.0190 (13) | 0.0228 (14) | 0.0221 (13) | −0.0027 (10) | 0.0001 (11) | −0.0063 (11) |
| C14 | 0.0188 (12) | 0.0195 (14) | 0.0152 (12) | −0.0023 (10) | −0.0021 (9) | −0.0081 (10) |
| C15 | 0.0210 (14) | 0.0238 (15) | 0.0205 (13) | −0.0042 (11) | −0.0007 (11) | −0.0082 (11) |
| C16 | 0.0343 (16) | 0.0196 (15) | 0.0277 (14) | 0.0022 (12) | −0.0050 (12) | −0.0091 (12) |
| C17 | 0.0448 (18) | 0.0187 (16) | 0.0238 (14) | −0.0086 (13) | 0.0007 (12) | −0.0070 (12) |
| C18 | 0.0292 (16) | 0.0316 (17) | 0.0293 (15) | −0.0142 (13) | 0.0073 (12) | −0.0145 (13) |
| C19 | 0.0192 (13) | 0.0257 (15) | 0.0264 (14) | −0.0030 (12) | 0.0012 (11) | −0.0120 (12) |
Geometric parameters (Å, º)
| P1—C1 | 1.787 (2) | C8—C13 | 1.401 (3) |
| P1—C2 | 1.796 (2) | C9—C10 | 1.390 (3) |
| P1—C8 | 1.805 (2) | C9—H9 | 0.96 (2) |
| P1—C14 | 1.804 (2) | C10—C11 | 1.373 (4) |
| B1—F3 | 1.394 (3) | C10—H10 | 0.96 (2) |
| B1—F2 | 1.400 (3) | C11—C12 | 1.388 (4) |
| B1—F1 | 1.404 (3) | C11—H11 | 0.89 (2) |
| B1—C1 | 1.636 (4) | C12—C13 | 1.383 (3) |
| C1—H1A | 0.96 (3) | C12—H12 | 0.95 (3) |
| C1—H1B | 0.92 (3) | C13—H13 | 0.99 (2) |
| C2—C3 | 1.394 (3) | C14—C15 | 1.395 (3) |
| C2—C7 | 1.395 (3) | C14—C19 | 1.401 (3) |
| C3—C4 | 1.383 (3) | C15—C16 | 1.385 (3) |
| C3—H3 | 0.97 (3) | C15—H15 | 0.94 (2) |
| C4—C5 | 1.380 (4) | C16—C17 | 1.385 (4) |
| C4—H4 | 0.95 (2) | C16—H16 | 0.99 (3) |
| C5—C6 | 1.377 (4) | C17—C18 | 1.385 (4) |
| C5—H5 | 0.94 (2) | C17—H17 | 0.99 (3) |
| C6—C7 | 1.385 (3) | C18—C19 | 1.378 (3) |
| C6—H6 | 0.95 (2) | C18—H18 | 0.92 (3) |
| C7—H7 | 1.00 (2) | C19—H19 | 0.97 (2) |
| C8—C9 | 1.394 (3) | ||
| C1—P1—C2 | 111.67 (12) | C9—C8—C13 | 119.8 (2) |
| C1—P1—C8 | 108.25 (11) | C9—C8—P1 | 122.17 (18) |
| C2—P1—C8 | 108.48 (10) | C13—C8—P1 | 118.04 (17) |
| C1—P1—C14 | 113.04 (12) | C10—C9—C8 | 119.6 (2) |
| C2—P1—C14 | 107.54 (10) | C10—C9—H9 | 117.9 (13) |
| C8—P1—C14 | 107.70 (11) | C8—C9—H9 | 122.5 (13) |
| F3—B1—F2 | 109.0 (2) | C11—C10—C9 | 120.4 (2) |
| F3—B1—F1 | 108.4 (2) | C11—C10—H10 | 121.1 (14) |
| F2—B1—F1 | 108.5 (2) | C9—C10—H10 | 118.5 (14) |
| F3—B1—C1 | 110.9 (2) | C10—C11—C12 | 120.6 (2) |
| F2—B1—C1 | 109.1 (2) | C10—C11—H11 | 121.3 (15) |
| F1—B1—C1 | 110.84 (19) | C12—C11—H11 | 118.1 (15) |
| B1—C1—P1 | 119.66 (17) | C13—C12—C11 | 119.9 (2) |
| B1—C1—H1A | 111.2 (15) | C13—C12—H12 | 119.0 (15) |
| P1—C1—H1A | 105.1 (15) | C11—C12—H12 | 121.1 (15) |
| B1—C1—H1B | 110.3 (16) | C12—C13—C8 | 119.8 (2) |
| P1—C1—H1B | 103.3 (16) | C12—C13—H13 | 120.1 (13) |
| H1A—C1—H1B | 106 (2) | C8—C13—H13 | 120.1 (13) |
| C3—C2—C7 | 119.4 (2) | C15—C14—C19 | 119.2 (2) |
| C3—C2—P1 | 120.63 (17) | C15—C14—P1 | 121.19 (17) |
| C7—C2—P1 | 119.90 (17) | C19—C14—P1 | 119.50 (18) |
| C4—C3—C2 | 119.7 (2) | C16—C15—C14 | 120.3 (2) |
| C4—C3—H3 | 122.1 (16) | C16—C15—H15 | 117.2 (14) |
| C2—C3—H3 | 118.0 (16) | C14—C15—H15 | 122.5 (14) |
| C5—C4—C3 | 120.6 (3) | C17—C16—C15 | 120.0 (3) |
| C5—C4—H4 | 120.7 (14) | C17—C16—H16 | 120.0 (15) |
| C3—C4—H4 | 118.7 (14) | C15—C16—H16 | 120.0 (15) |
| C6—C5—C4 | 120.0 (2) | C16—C17—C18 | 120.1 (3) |
| C6—C5—H5 | 118.9 (15) | C16—C17—H17 | 118.8 (15) |
| C4—C5—H5 | 121.1 (15) | C18—C17—H17 | 121.2 (15) |
| C5—C6—C7 | 120.3 (2) | C19—C18—C17 | 120.4 (3) |
| C5—C6—H6 | 119.8 (15) | C19—C18—H18 | 120.3 (16) |
| C7—C6—H6 | 119.9 (15) | C17—C18—H18 | 119.2 (16) |
| C6—C7—C2 | 120.0 (2) | C18—C19—C14 | 120.0 (2) |
| C6—C7—H7 | 120.3 (13) | C18—C19—H19 | 120.6 (13) |
| C2—C7—H7 | 119.6 (13) | C14—C19—H19 | 119.4 (13) |
| F3—B1—C1—P1 | 81.6 (2) | C2—P1—C8—C13 | 177.28 (18) |
| F2—B1—C1—P1 | −158.33 (17) | C14—P1—C8—C13 | −66.6 (2) |
| F1—B1—C1—P1 | −38.9 (3) | C13—C8—C9—C10 | 0.4 (3) |
| C2—P1—C1—B1 | 68.2 (2) | P1—C8—C9—C10 | 178.94 (18) |
| C8—P1—C1—B1 | −172.42 (19) | C8—C9—C10—C11 | 0.6 (4) |
| C14—P1—C1—B1 | −53.2 (2) | C9—C10—C11—C12 | −0.8 (4) |
| C1—P1—C2—C3 | 25.8 (2) | C10—C11—C12—C13 | 0.1 (4) |
| C8—P1—C2—C3 | −93.4 (2) | C11—C12—C13—C8 | 0.8 (4) |
| C14—P1—C2—C3 | 150.38 (18) | C9—C8—C13—C12 | −1.1 (3) |
| C1—P1—C2—C7 | −156.73 (19) | P1—C8—C13—C12 | −179.71 (19) |
| C8—P1—C2—C7 | 84.1 (2) | C1—P1—C14—C15 | −119.9 (2) |
| C14—P1—C2—C7 | −32.2 (2) | C2—P1—C14—C15 | 116.40 (19) |
| C7—C2—C3—C4 | −0.1 (4) | C8—P1—C14—C15 | −0.3 (2) |
| P1—C2—C3—C4 | 177.32 (19) | C1—P1—C14—C19 | 63.0 (2) |
| C2—C3—C4—C5 | −0.3 (4) | C2—P1—C14—C19 | −60.7 (2) |
| C3—C4—C5—C6 | 0.2 (4) | C8—P1—C14—C19 | −177.42 (18) |
| C4—C5—C6—C7 | 0.5 (4) | C19—C14—C15—C16 | −0.4 (3) |
| C5—C6—C7—C2 | −1.0 (4) | P1—C14—C15—C16 | −177.49 (18) |
| C3—C2—C7—C6 | 0.8 (4) | C14—C15—C16—C17 | 0.4 (4) |
| P1—C2—C7—C6 | −176.70 (18) | C15—C16—C17—C18 | −0.5 (4) |
| C1—P1—C8—C9 | −122.6 (2) | C16—C17—C18—C19 | 0.6 (4) |
| C2—P1—C8—C9 | −1.3 (2) | C17—C18—C19—C14 | −0.6 (4) |
| C14—P1—C8—C9 | 114.8 (2) | C15—C14—C19—C18 | 0.5 (3) |
| C1—P1—C8—C13 | 55.9 (2) |
Hydrogen-bond geometry (Å, º)
Cg1 is the centroid of the C2–C7 ring.
| D—H···A | D—H | H···A | D···A | D—H···A |
| C4—H4···F1i | 0.95 (3) | 2.44 (2) | 3.293 (4) | 149.7 (17) |
| C12—H12···F1ii | 0.96 (3) | 2.37 (3) | 3.084 (3) | 131 (2) |
| C19—H19···F1 | 0.97 (2) | 2.43 (2) | 3.263 (3) | 143.9 (18) |
| C11—H11···Cgii | 0.89 (3) | 2.77 (3) | 3.639 (3) | 165 (2) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, y, z.
Funding Statement
This work was funded by Eastern Washington University Faculty Grants for Research and Creative Works grant .
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989017009884/lh5846sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989017009884/lh5846Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989017009884/lh5846Isup3.cml
CCDC reference: 1560028
Additional supporting information: crystallographic information; 3D view; checkCIF report