The bulky tert-butyl groups of the dbbpy ligand do not preclude the formation of head-to-head dimers in the crystal structure of bis(acetonitrile)(4,4′-di-tert-butyl-2,2′-bipyridine)platinum(II) tetrafluoridoborate.
Keywords: supramolecular, platinum(II), crystal structure
Abstract
The crystal structure of a platinum(II) supramolecular building block, [Pt(dbbpy)(NCCH3)2](BF4)2 (dbbpy = 4,4′-di-tert-butyl-2,2′-bipyridine, C18H24N2) is an example of a rare head-to-head dimer, even with the bulky tert-butyl groups of the bipyridine. This packing motif still enables significant π–π interactions between two pyridyl groups, and may result from the close proximity of the tetrafluoridoborate ions to the platinum(II) complexes, resulting in intramolecular H⋯F distances between 2.156 and 2.573 Å.
Chemical context
The title compound is soluble in a diverse range of solvents and possesses exchangeable acetonitrile ligands for facile incorporation of novel ligands to develop new and diverse behaviors of platinum(II) complexes. The solubility and apt geometry of the (dbbpy)platinum(II) complex make it a desirable building block for coordination-driven self-assembly of homo-metallic (Zhang, et al., 2017 ▸) and hetero-metallic (Bera et al., 2001 ▸) supramolecular complexes. This platinum(II) diimine can also be combined with dithiolene ligands to study methylation kinetics (Stace, et al., 2016 ▸), generate charge-transfer materials (Smucker, et al., 2003 ▸), or make model complexes for examining photophysical properties (Lazarides, et al., 2011 ▸; Yang et al., 2014 ▸).
Structural commentary
The platinum–nitrogen distances for the bipyridyl N1 and N2 of the +2 cation are 1.994 (4) and 1.995 (4) Å, respectively, with a bond angle of 80.5 (2)°. These are shorter than those affected by the stronger trans-influence of chloride in two structures of the neutral (dbbpy)PtCl2 molecule: one with Pt—N distances of 2.013 (2) and 2.011 (2) Å and a 79.79 (6)° N—Pt—N angle (Day, 2009 ▸), and the other having Pt—N distances of 2.010 (12) and 2.019 (10) Å and a 78.7 (5)° N—Pt—N angle (Achar & Catalano, 1997 ▸). The Pt—N distances of the title compound are longer than those having the weaker trans-influence of water in the +2 cation of [(dbbpy)Pt(OH2)2](OTf)2 (Singh et al., 2008 ▸), which exhibits Pt—N distances of 1.966 (5) and 1.974 (5) Å and the resulting wider bond angle of 81.1 (2)° for N—Pt—N. The trans-influence of the ligand is, indeed, on par with that of the related mono-cation [(dbbpy)Pt(NCCH3)(Ph)] [BAr’4], containing a Pt—N distance of 2.000 (4) Å, located trans to the acetonitrile, while the phenyl ligand causes an elongation to 2.092 (4) Å for the other Pt—N bond (McKeown, et al., 2011 ▸).
Supramolecular features
Most platinum(II) compounds containing the bulky dbbpy ligand pack as head-to-tail dimers, such as the aforementioned (dbbpy)PtCl2 (Day, 2009 ▸; Achar & Catalano, 1997 ▸), [(dbbpy)Pt(OH2)2](OTf)2 (Singh et al., 2008 ▸), [(dbbpy)Pt(NCCH3)(Ph)][BAr′4] (Ar′ = 3,5-bis(trifluoromethyl)phenyl; McKeown et al., 2011 ▸), and (dbbpy)Pt(dmid) (dmid = 1,3-dithiole-2-one-4,5-dithiolate; Smucker et al., 2003 ▸). The cations in the title compound, however, pack as head-to-head dimers (Figs. 1 ▸ and 2 ▸). In these dimers, the molecules are offset (translation by half a molecule)and slightly canted [the planes composed of all non-H atoms except the tert-butly groups for the (dbbpy)Pt(NCCH3)2 cation and its corresponding dimer (−x, y, 
− z) are at an angle of 10.82°], both of which accommodate the bulky tert-butyl groups of the dbbpy ligands. The intramolecular Pt—Pt distance is quite long at 4.5123 (3) Å, yet the pyridyl rings of the dbbpy are positioned for π–π interactions with distances between 3.616 (5) Å (N1⋯N1i) and 4.032 (7) Å (C4⋯C4i) [symmetry code: (i) −x, y, − z] occurring between the two rings (Fig. 2 ▸). This atypical head-to-head packing may be partly explained through the favorable non-polar interactions between the tert-butyl groups. Another viable explanation comes through the intermolecular interactions between fluorine atoms of the BF4
− ions and the hydrogen atoms on the pyridine and acetonitrile ligands on multiple cations. Indeed, all eight fluorine atoms of the two unique BF4
− anions are in close proximity to hydrogen atoms on the cation with intermolecular H⋯F distances between 2.16 and 2.57 Å (Fig. 1 ▸ and Table 1 ▸). Changing the anion in related bis(acetonitrile)(diimine) platinum(II) cations seems to have a significant influence, as observed in the structures of 2,2′-bipyridine in [(bpy)Pt(NCCH3)2](OTf)2 (Field et al., 2003 ▸) or 1,10-phenanthroline in [(phen)Pt(NCCh3)2](ClO4)2 (Ha, 2010 ▸), which do not form dimers as the positions of the triflate or perchlorate anions minimize the close proximity of the two platinum-containing cations.
Figure 1.
Displacement ellipsoid plot (50% probability of all non-H atoms), illustrating the head-to-head dimer with selected H⋯F intermolecular distances (Å) between a BF4 − anion and acetonitrile molecules on adjacent molecules.
Figure 2.
Displacement ellipsoid plot (50% probability of all non-H atoms), illustrating the slightly canted head-to-head dimer with selected intramolecular distances shown.
Table 1. Intermolecular H⋯F distances (Å) between all eight fluorine atoms of the two BF4 − anions.
| F1⋯H1A | 2.16 | F5iii⋯H7A iv | 2.30 |
| F1⋯H20B | 2.43 | F5iii⋯H4A iv | 2.35 |
| F2⋯H9A ii | 2.43 | F6iii⋯H20C i | 2.28 |
| F3⋯H9A ii | 2.57 | F7iii⋯H20A | 2.34 |
| F4⋯H2A | 2.43 (4) | F8iii⋯H22C | 2.34 |
Symmetry codes: (i) −x, y, 
− z; (ii) x, 1 − y, + z; (iii) − x, + y, z; (iv) x, 1 + y, z.
Synthesis
The synthesis of the title compound used a method which replaced the chloride from Pt(dbbpy)Cl2 (Tzeng et al., 2001 ▸) with acetonitrile using excess AgBF4 by following the general syntheses of (dbbpy)Pt(SO3CF3)2 (Hill et al., 1996 ▸) and [Pt(NCCH3)4](BF4)2 (de Renzi et al., 1976 ▸).
[Pt(dbbpy)(NCCH3)2](BF4)2 A solution containing 25 mL of acetonitrile, 200.7 mg (0.2500 mmol) of Pt(dbbpy)Cl2, and 164 mg (0.8425 mmol) of AgBF4 was refluxed under stirring until a yellow solution formed. The solution was isolated, via cannula, from the AgCl precipitate and condensed under reduced pressure until ∼5 mL of orange solution remained. This was combined with 25 ml of Et2O and the resulting precipitate was washed with 3 × 20 mL Et2O to give 206.9 mg (83.8% yield) of product. UV–vis λmax (∊ Lmol−1cm−1): 211 (4.6 × 104), 249 (4.2 × 104), 306 (2.0 × 104), 319 (2.4 × 104) and 346 (6.0 × 103) nm.
Yellow crystals of the title compound were grown from liquid diffusion of hexanes into a dilute acetone solution.
Refinement
Crystal data, data collection and structure refinement details are summarized in Table 2 ▸. H atoms were attached to C atoms and ideally positioned (C—H = 0.95–0.98 Å) and refined as riding with U iso(H) = 1.2U eq(CH) or U iso(H) = 1.2U eq(CH3).
Table 2. Experimental details.
| Crystal data | |
| Chemical formula | [Pt(C18H24N2)(C2H3N)2](BF4)2 |
| M r | 719.21 |
| Crystal system, space group | Orthorhombic, P b c n |
| Temperature (K) | 100 |
| a, b, c (Å) | 16.3409 (10), 13.0447 (8), 25.1105 (16) |
| V (Å3) | 5352.6 (6) |
| Z | 8 |
| Radiation type | Mo Kα |
| μ (mm−1) | 5.32 |
| Crystal size (mm) | 0.14 × 0.14 × 0.08 |
| Data collection | |
| Diffractometer | Bruker APEXII CCD |
| Absorption correction | Multi-scan (SADABS; Bruker, 2001 ▸) |
| T min, T max | 0.515, 0.682 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 61655, 5919, 4823 |
| R int | 0.048 |
| (sin θ/λ)max (Å−1) | 0.641 |
| Refinement | |
| R[F 2 > 2σ(F 2)], wR(F 2), S | 0.033, 0.113, 1.01 |
| No. of reflections | 5919 |
| No. of parameters | 342 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 1.39, −1.56 |
Supplementary Material
Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989018005923/jj2198sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989018005923/jj2198Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989018005923/jj2198Isup3.mol
CCDC reference: 1837532
Additional supporting information: crystallographic information; 3D view; checkCIF report
Acknowledgments
X-ray data were collected at the University of North Texas using a Bruker APEXII CCD diffractometer.
supplementary crystallographic information
Crystal data
| [Pt(C18H24N2)(C2H3N)2](BF4)2 | F(000) = 2800 |
| Mr = 719.21 | Dx = 1.785 Mg m−3 |
| Orthorhombic, Pbcn | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2n 2ab | Cell parameters from 9946 reflections |
| a = 16.3409 (10) Å | θ = 2.2–27.1° |
| b = 13.0447 (8) Å | µ = 5.32 mm−1 |
| c = 25.1105 (16) Å | T = 100 K |
| V = 5352.6 (6) Å3 | Plate, yellow |
| Z = 8 | 0.14 × 0.14 × 0.08 mm |
Data collection
| Bruker APEXII CCD diffractometer | 5919 independent reflections |
| Radiation source: fine-focus sealed tube | 4823 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.048 |
| ω scans | θmax = 27.1°, θmin = 1.6° |
| Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −20→20 |
| Tmin = 0.515, Tmax = 0.682 | k = −16→16 |
| 61655 measured reflections | l = −32→32 |
Refinement
| 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)] = 0.033 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.113 | H-atom parameters constrained |
| S = 1.01 | w = 1/[σ2(Fo2) + (0.080P)2 + 5.P] where P = (Fo2 + 2Fc2)/3 |
| 5919 reflections | (Δ/σ)max = 0.001 |
| 342 parameters | Δρmax = 1.39 e Å−3 |
| 0 restraints | Δρmin = −1.55 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. |
| 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 > 2sigma(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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| Pt1 | 0.098683 (11) | 0.487050 (15) | 0.187162 (8) | 0.02001 (9) | |
| N1 | 0.1092 (2) | 0.3711 (3) | 0.23845 (16) | 0.0200 (8) | |
| C1 | 0.1088 (3) | 0.3805 (4) | 0.29169 (19) | 0.0230 (10) | |
| H1A | 0.1042 | 0.4469 | 0.3070 | 0.028* | |
| N2 | 0.1029 (2) | 0.3703 (3) | 0.13593 (17) | 0.0227 (9) | |
| C2 | 0.1149 (3) | 0.2965 (4) | 0.3246 (2) | 0.0261 (11) | |
| H2A | 0.1140 | 0.3054 | 0.3622 | 0.031* | |
| N3 | 0.1005 (2) | 0.5974 (3) | 0.24244 (18) | 0.0247 (9) | |
| C3 | 0.1223 (3) | 0.1981 (4) | 0.30320 (17) | 0.0188 (9) | |
| N4 | 0.0870 (2) | 0.5961 (3) | 0.13214 (18) | 0.0261 (9) | |
| C4 | 0.1233 (3) | 0.1908 (3) | 0.24737 (17) | 0.0203 (9) | |
| H4A | 0.1280 | 0.1254 | 0.2310 | 0.024* | |
| C5 | 0.1174 (3) | 0.2771 (4) | 0.21635 (17) | 0.0197 (9) | |
| C6 | 0.1182 (3) | 0.2775 (4) | 0.15764 (18) | 0.0214 (10) | |
| C7 | 0.1341 (3) | 0.1931 (3) | 0.12624 (17) | 0.0197 (9) | |
| H7A | 0.1449 | 0.1288 | 0.1425 | 0.024* | |
| C8 | 0.1346 (3) | 0.2010 (4) | 0.07074 (18) | 0.0235 (10) | |
| C9 | 0.1159 (3) | 0.2968 (4) | 0.0501 (2) | 0.0282 (11) | |
| H9A | 0.1142 | 0.3057 | 0.0125 | 0.034* | |
| C10 | 0.0999 (3) | 0.3787 (4) | 0.08242 (19) | 0.0281 (12) | |
| H10A | 0.0864 | 0.4429 | 0.0669 | 0.034* | |
| C11 | 0.1265 (3) | 0.1023 (4) | 0.33750 (18) | 0.0224 (10) | |
| C12 | 0.2078 (3) | 0.0461 (4) | 0.32623 (19) | 0.0261 (10) | |
| H12A | 0.2115 | 0.0299 | 0.2882 | 0.039* | |
| H12B | 0.2099 | −0.0174 | 0.3470 | 0.039* | |
| H12C | 0.2538 | 0.0903 | 0.3364 | 0.039* | |
| C13 | 0.0557 (3) | 0.0306 (4) | 0.3229 (2) | 0.0274 (11) | |
| H13A | 0.0624 | 0.0069 | 0.2861 | 0.041* | |
| H13B | 0.0038 | 0.0675 | 0.3263 | 0.041* | |
| H13C | 0.0557 | −0.0285 | 0.3470 | 0.041* | |
| C14 | 0.1207 (3) | 0.1287 (4) | 0.39695 (19) | 0.0315 (12) | |
| H14A | 0.0716 | 0.1698 | 0.4034 | 0.047* | |
| H14B | 0.1693 | 0.1677 | 0.4076 | 0.047* | |
| H14C | 0.1177 | 0.0653 | 0.4178 | 0.047* | |
| C15 | 0.1569 (3) | 0.1088 (4) | 0.03663 (18) | 0.0249 (10) | |
| C16 | 0.0911 (4) | 0.0262 (4) | 0.0438 (2) | 0.0344 (13) | |
| H16A | 0.0875 | 0.0072 | 0.0815 | 0.052* | |
| H16B | 0.1057 | −0.0344 | 0.0227 | 0.052* | |
| H16C | 0.0382 | 0.0528 | 0.0317 | 0.052* | |
| C17 | 0.2397 (3) | 0.0657 (5) | 0.0539 (2) | 0.0389 (13) | |
| H17A | 0.2383 | 0.0504 | 0.0921 | 0.058* | |
| H17B | 0.2826 | 0.1163 | 0.0468 | 0.058* | |
| H17C | 0.2512 | 0.0027 | 0.0340 | 0.058* | |
| C18 | 0.1638 (4) | 0.1369 (4) | −0.02260 (19) | 0.0379 (14) | |
| H18A | 0.1101 | 0.1584 | −0.0359 | 0.057* | |
| H18B | 0.1826 | 0.0771 | −0.0428 | 0.057* | |
| H18C | 0.2029 | 0.1932 | −0.0269 | 0.057* | |
| C19 | 0.1018 (3) | 0.6625 (4) | 0.2714 (2) | 0.0249 (11) | |
| C20 | 0.1019 (3) | 0.7449 (5) | 0.3107 (2) | 0.0320 (13) | |
| H20A | 0.1448 | 0.7945 | 0.3019 | 0.048* | |
| H20B | 0.1124 | 0.7162 | 0.3461 | 0.048* | |
| H20C | 0.0486 | 0.7793 | 0.3106 | 0.048* | |
| C21 | 0.0799 (3) | 0.6560 (4) | 0.1006 (2) | 0.0282 (11) | |
| C22 | 0.0702 (4) | 0.7321 (4) | 0.0583 (2) | 0.0435 (15) | |
| H22B | 0.0863 | 0.7018 | 0.0241 | 0.065* | |
| H22C | 0.1049 | 0.7916 | 0.0659 | 0.065* | |
| H22A | 0.0129 | 0.7538 | 0.0565 | 0.065* | |
| F5 | 0.3387 (3) | 0.4742 (3) | 0.18538 (12) | 0.0439 (9) | |
| F1 | 0.0964 (2) | 0.5412 (3) | 0.37735 (13) | 0.0444 (9) | |
| F6 | 0.4162 (2) | 0.3323 (3) | 0.18232 (14) | 0.0466 (9) | |
| F7 | 0.2907 (2) | 0.3270 (3) | 0.22056 (14) | 0.0499 (9) | |
| F8 | 0.3013 (2) | 0.3445 (3) | 0.13080 (14) | 0.0481 (9) | |
| F2 | 0.0499 (2) | 0.5587 (3) | 0.46122 (13) | 0.0498 (9) | |
| F3 | 0.1841 (2) | 0.5745 (3) | 0.44502 (13) | 0.0519 (10) | |
| F4 | 0.1237 (3) | 0.4179 (3) | 0.43888 (16) | 0.0742 (14) | |
| B1 | 0.1145 (5) | 0.5186 (6) | 0.4330 (2) | 0.0345 (16) | |
| B2 | 0.3361 (4) | 0.3695 (5) | 0.1792 (2) | 0.0293 (13) |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Pt1 | 0.02479 (13) | 0.01503 (13) | 0.02021 (13) | −0.00068 (6) | −0.00068 (7) | 0.00112 (6) |
| N1 | 0.025 (2) | 0.018 (2) | 0.018 (2) | −0.0017 (15) | −0.0023 (15) | −0.0012 (15) |
| C1 | 0.034 (3) | 0.018 (2) | 0.017 (2) | −0.0026 (19) | −0.0004 (19) | −0.0040 (19) |
| N2 | 0.031 (2) | 0.016 (2) | 0.022 (2) | −0.0061 (15) | −0.0026 (16) | 0.0006 (16) |
| C2 | 0.037 (3) | 0.023 (3) | 0.019 (2) | −0.001 (2) | −0.003 (2) | −0.002 (2) |
| N3 | 0.026 (2) | 0.021 (2) | 0.028 (2) | 0.0024 (15) | −0.0013 (16) | 0.0027 (18) |
| C3 | 0.021 (2) | 0.018 (2) | 0.018 (2) | −0.0039 (18) | 0.0009 (18) | 0.0024 (17) |
| N4 | 0.030 (2) | 0.018 (2) | 0.031 (2) | 0.0031 (16) | −0.0006 (17) | −0.0011 (18) |
| C4 | 0.023 (2) | 0.022 (2) | 0.016 (2) | −0.0032 (18) | −0.0004 (18) | −0.0033 (18) |
| C5 | 0.022 (2) | 0.019 (2) | 0.018 (2) | −0.0040 (17) | 0.0009 (18) | −0.0023 (17) |
| C6 | 0.022 (2) | 0.022 (2) | 0.020 (2) | −0.0055 (18) | −0.0032 (18) | 0.0021 (18) |
| C7 | 0.023 (2) | 0.017 (2) | 0.019 (2) | −0.0040 (18) | −0.0039 (18) | 0.0020 (17) |
| C8 | 0.030 (3) | 0.020 (2) | 0.021 (2) | −0.0075 (19) | −0.002 (2) | 0.0024 (18) |
| C9 | 0.044 (3) | 0.027 (3) | 0.013 (2) | −0.003 (2) | −0.003 (2) | 0.0052 (19) |
| C10 | 0.043 (3) | 0.023 (3) | 0.018 (3) | −0.005 (2) | −0.008 (2) | 0.0033 (19) |
| C11 | 0.029 (2) | 0.022 (2) | 0.017 (2) | 0.002 (2) | −0.0029 (19) | 0.0013 (18) |
| C12 | 0.029 (3) | 0.024 (2) | 0.026 (2) | 0.007 (2) | 0.003 (2) | 0.009 (2) |
| C13 | 0.031 (3) | 0.022 (2) | 0.029 (3) | −0.006 (2) | 0.001 (2) | 0.007 (2) |
| C14 | 0.046 (3) | 0.027 (3) | 0.021 (3) | 0.000 (2) | 0.000 (2) | 0.009 (2) |
| C15 | 0.034 (3) | 0.025 (2) | 0.016 (2) | −0.003 (2) | −0.0014 (19) | −0.0013 (19) |
| C16 | 0.049 (4) | 0.024 (3) | 0.030 (3) | 0.001 (2) | −0.003 (2) | −0.007 (2) |
| C17 | 0.037 (3) | 0.051 (4) | 0.028 (3) | 0.006 (3) | 0.006 (2) | 0.006 (3) |
| C18 | 0.066 (4) | 0.035 (3) | 0.013 (2) | 0.006 (3) | −0.002 (2) | −0.003 (2) |
| C19 | 0.029 (3) | 0.023 (3) | 0.023 (3) | 0.0030 (19) | 0.002 (2) | −0.002 (2) |
| C20 | 0.041 (3) | 0.022 (3) | 0.032 (3) | 0.001 (2) | 0.000 (2) | −0.006 (2) |
| C21 | 0.032 (3) | 0.023 (3) | 0.029 (3) | 0.008 (2) | 0.005 (2) | 0.005 (2) |
| C22 | 0.057 (4) | 0.032 (3) | 0.041 (4) | 0.009 (3) | −0.006 (3) | 0.022 (3) |
| F5 | 0.056 (2) | 0.033 (2) | 0.042 (2) | 0.0095 (17) | 0.0005 (15) | 0.0018 (15) |
| F1 | 0.054 (2) | 0.052 (2) | 0.0273 (18) | 0.0104 (16) | −0.0050 (14) | −0.0065 (17) |
| F6 | 0.0295 (17) | 0.041 (2) | 0.070 (3) | 0.0038 (15) | 0.0019 (15) | −0.0015 (17) |
| F7 | 0.0379 (19) | 0.060 (2) | 0.052 (2) | −0.0054 (16) | 0.0043 (16) | 0.0274 (19) |
| F8 | 0.049 (2) | 0.049 (2) | 0.046 (2) | −0.0100 (17) | −0.0084 (16) | −0.0111 (16) |
| F2 | 0.051 (2) | 0.064 (3) | 0.0348 (19) | −0.0122 (19) | 0.0087 (16) | −0.0163 (17) |
| F3 | 0.046 (2) | 0.074 (3) | 0.0358 (19) | −0.0100 (19) | 0.0048 (15) | −0.0153 (18) |
| F4 | 0.132 (4) | 0.035 (2) | 0.056 (3) | 0.012 (2) | −0.024 (3) | −0.004 (2) |
| B1 | 0.035 (3) | 0.046 (4) | 0.023 (3) | 0.014 (3) | −0.009 (3) | −0.026 (3) |
| B2 | 0.023 (3) | 0.022 (3) | 0.043 (4) | −0.005 (2) | 0.003 (2) | 0.005 (2) |
Geometric parameters (Å, º)
| Pt1—N4 | 1.992 (4) | C13—H13B | 0.9800 |
| Pt1—N1 | 1.994 (4) | C13—H13C | 0.9800 |
| Pt1—N2 | 1.995 (4) | C14—H14A | 0.9800 |
| Pt1—N3 | 2.000 (5) | C14—H14B | 0.9800 |
| N1—C1 | 1.343 (6) | C14—H14C | 0.9800 |
| N1—C5 | 1.353 (6) | C15—C17 | 1.528 (7) |
| C1—C2 | 1.377 (7) | C15—C16 | 1.533 (7) |
| C1—H1A | 0.9500 | C15—C18 | 1.536 (6) |
| N2—C10 | 1.349 (6) | C16—H16A | 0.9800 |
| N2—C6 | 1.350 (6) | C16—H16B | 0.9800 |
| C2—C3 | 1.396 (7) | C16—H16C | 0.9800 |
| C2—H2A | 0.9500 | C17—H17A | 0.9800 |
| N3—C19 | 1.118 (7) | C17—H17B | 0.9800 |
| C3—C4 | 1.405 (6) | C17—H17C | 0.9800 |
| C3—C11 | 1.520 (6) | C18—H18A | 0.9800 |
| N4—C21 | 1.119 (7) | C18—H18B | 0.9800 |
| C4—C5 | 1.372 (6) | C18—H18C | 0.9800 |
| C4—H4A | 0.9500 | C19—C20 | 1.460 (7) |
| C5—C6 | 1.474 (6) | C20—H20A | 0.9800 |
| C6—C7 | 1.379 (6) | C20—H20B | 0.9800 |
| C7—C8 | 1.398 (6) | C20—H20C | 0.9800 |
| C7—H7A | 0.9500 | C21—C22 | 1.462 (7) |
| C8—C9 | 1.386 (7) | C22—H22B | 0.9800 |
| C8—C15 | 1.521 (7) | C22—H22C | 0.9800 |
| C9—C10 | 1.368 (8) | C22—H22A | 0.9800 |
| C9—H9A | 0.9500 | F5—B2 | 1.375 (7) |
| C10—H10A | 0.9500 | F1—B1 | 1.459 (7) |
| C11—C13 | 1.532 (7) | F6—B2 | 1.398 (7) |
| C11—C14 | 1.535 (6) | F7—B2 | 1.392 (6) |
| C11—C12 | 1.544 (7) | F8—B2 | 1.381 (7) |
| C12—H12A | 0.9800 | F2—B1 | 1.374 (7) |
| C12—H12B | 0.9800 | F3—B1 | 1.385 (8) |
| C12—H12C | 0.9800 | F4—B1 | 1.330 (8) |
| C13—H13A | 0.9800 | ||
| N4—Pt1—N1 | 176.23 (16) | C11—C13—H13C | 109.5 |
| N4—Pt1—N2 | 95.81 (18) | H13A—C13—H13C | 109.5 |
| N1—Pt1—N2 | 80.47 (18) | H13B—C13—H13C | 109.5 |
| N4—Pt1—N3 | 88.22 (19) | C11—C14—H14A | 109.5 |
| N1—Pt1—N3 | 95.53 (18) | C11—C14—H14B | 109.5 |
| N2—Pt1—N3 | 175.27 (16) | H14A—C14—H14B | 109.5 |
| C1—N1—C5 | 119.5 (4) | C11—C14—H14C | 109.5 |
| C1—N1—Pt1 | 125.0 (3) | H14A—C14—H14C | 109.5 |
| C5—N1—Pt1 | 115.6 (3) | H14B—C14—H14C | 109.5 |
| N1—C1—C2 | 121.7 (5) | C8—C15—C17 | 110.1 (4) |
| N1—C1—H1A | 119.2 | C8—C15—C16 | 108.8 (4) |
| C2—C1—H1A | 119.2 | C17—C15—C16 | 109.2 (4) |
| C10—N2—C6 | 118.8 (4) | C8—C15—C18 | 112.0 (4) |
| C10—N2—Pt1 | 125.4 (4) | C17—C15—C18 | 107.4 (4) |
| C6—N2—Pt1 | 115.5 (3) | C16—C15—C18 | 109.4 (4) |
| C1—C2—C3 | 120.4 (5) | C15—C16—H16A | 109.5 |
| C1—C2—H2A | 119.8 | C15—C16—H16B | 109.5 |
| C3—C2—H2A | 119.8 | H16A—C16—H16B | 109.5 |
| C19—N3—Pt1 | 176.6 (4) | C15—C16—H16C | 109.5 |
| C2—C3—C4 | 116.7 (4) | H16A—C16—H16C | 109.5 |
| C2—C3—C11 | 122.8 (4) | H16B—C16—H16C | 109.5 |
| C4—C3—C11 | 120.6 (4) | C15—C17—H17A | 109.5 |
| C21—N4—Pt1 | 178.7 (5) | C15—C17—H17B | 109.5 |
| C5—C4—C3 | 120.6 (4) | H17A—C17—H17B | 109.5 |
| C5—C4—H4A | 119.7 | C15—C17—H17C | 109.5 |
| C3—C4—H4A | 119.7 | H17A—C17—H17C | 109.5 |
| N1—C5—C4 | 121.2 (4) | H17B—C17—H17C | 109.5 |
| N1—C5—C6 | 114.0 (4) | C15—C18—H18A | 109.5 |
| C4—C5—C6 | 124.8 (4) | C15—C18—H18B | 109.5 |
| N2—C6—C7 | 121.3 (4) | H18A—C18—H18B | 109.5 |
| N2—C6—C5 | 114.0 (4) | C15—C18—H18C | 109.5 |
| C7—C6—C5 | 124.7 (4) | H18A—C18—H18C | 109.5 |
| C6—C7—C8 | 120.8 (4) | H18B—C18—H18C | 109.5 |
| C6—C7—H7A | 119.6 | N3—C19—C20 | 177.7 (6) |
| C8—C7—H7A | 119.6 | C19—C20—H20A | 109.5 |
| C9—C8—C7 | 116.0 (4) | C19—C20—H20B | 109.5 |
| C9—C8—C15 | 123.7 (4) | H20A—C20—H20B | 109.5 |
| C7—C8—C15 | 120.3 (4) | C19—C20—H20C | 109.5 |
| C10—C9—C8 | 121.6 (5) | H20A—C20—H20C | 109.5 |
| C10—C9—H9A | 119.2 | H20B—C20—H20C | 109.5 |
| C8—C9—H9A | 119.2 | N4—C21—C22 | 178.4 (6) |
| N2—C10—C9 | 121.4 (5) | C21—C22—H22B | 109.5 |
| N2—C10—H10A | 119.3 | C21—C22—H22C | 109.5 |
| C9—C10—H10A | 119.3 | H22B—C22—H22C | 109.5 |
| C3—C11—C13 | 109.4 (4) | C21—C22—H22A | 109.5 |
| C3—C11—C14 | 111.3 (4) | H22B—C22—H22A | 109.5 |
| C13—C11—C14 | 108.9 (4) | H22C—C22—H22A | 109.5 |
| C3—C11—C12 | 109.0 (4) | F4—B1—F2 | 113.9 (7) |
| C13—C11—C12 | 108.5 (4) | F4—B1—F3 | 113.8 (5) |
| C14—C11—C12 | 109.7 (4) | F2—B1—F3 | 108.6 (4) |
| C11—C12—H12A | 109.5 | F4—B1—F1 | 109.1 (5) |
| C11—C12—H12B | 109.5 | F2—B1—F1 | 105.1 (5) |
| H12A—C12—H12B | 109.5 | F3—B1—F1 | 105.6 (6) |
| C11—C12—H12C | 109.5 | F5—B2—F8 | 110.2 (5) |
| H12A—C12—H12C | 109.5 | F5—B2—F7 | 109.1 (5) |
| H12B—C12—H12C | 109.5 | F8—B2—F7 | 110.0 (4) |
| C11—C13—H13A | 109.5 | F5—B2—F6 | 108.0 (5) |
| C11—C13—H13B | 109.5 | F8—B2—F6 | 110.7 (5) |
| H13A—C13—H13B | 109.5 | F7—B2—F6 | 108.7 (5) |
Funding Statement
This work was funded by Welch Foundation grant AD-0007 to the Chemistry Department at Austin College for Undergraduate Research.
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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/S2056989018005923/jj2198sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989018005923/jj2198Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989018005923/jj2198Isup3.mol
CCDC reference: 1837532
Additional supporting information: crystallographic information; 3D view; checkCIF report