research communications
A five-coordinate cobalt bis(dithiolene)–phosphine complex [Co(pdt)2(PTA)] (pdt = phenyldithiolene; PTA = 1,3,5-triaza-7-phosphaadamantane)
aDepartment of Chemistry & Biochemistry, Lamar University, 4400 S. M.L.K. King Jr. Pkwy, Beaumont, TX 77705, USA, and bDepartment of Chemistry & Biochemistry, California State Polytechnic University, Pomona, 3801 W. Temple Ave., Pomona, CA 91768, USA
*Correspondence e-mail: pchandraseka@lamar.edu, sestieber@cpp.edu
The title compound, bis(1,2-diphenyl-2-sulfanylideneethanethiolato-κ2S,S′)(1,3,5-triaza-7-phosphaadamantane-κP)cobalt(II) dichloromethane hemisolvate, [Co(pdt)2(PTA)]·0.5C2H4Cl2 or [Co(C14H10S2)2(C6H12N3P)]·0.5C2H4Cl2, contains two phenyldithiolene (pdt) ligands and a 1,3,5-triaza-7-phosphaadamantane (PTA) ligand bound to cobalt with the solvent 1,2-dichloroethane molecule located on an inversion center. The cobalt core exhibits an approximately square-pyramidal geometry with partially reduced thienyl radical monoanionic ligands. The supramolecular network is consolidated by hydrogen-bonding interactions primarily with nitrogen, sulfur and chlorine atoms, as well as parallel displaced π-stacking of the aryl rings. The UV–vis, IR, and CV data are also consistent with monoanionic dithiolene ligands and an overall CoII oxidation state.
Keywords: cobalt complex; dithiolene; redox-active; non-innocent ligand; PTA ligand; crystal structure.
CCDC reference: 1986931
1. Chemical context
Transition-metal complexes of 1,3,5-triaza-7-phosphaadamantane (PTA) and related ligands have attracted much attention because of their potential as water-soluble catalysts, materials, and therapeutic agents (Guerriero et al., 2018). The small cone angle (103°) of the PTA ligand combined with the high thermal and chemical stability, and high hydrophilicity makes it unique among phosphine ligands (Phillips et al., 2004). Electronically, the PTA ligand is much less electron donating than PMe3, while a slightly better than PPh3 (Darensbourg et al., 1999). However, the formation of heteroleptic dithiolene-phosphine complexes from the corresponding homoleptic metal-dithiolene has not been fully explored (Natarajan et al., 2017). Reactions of homoleptic metal-dithiolenes with to produce heteroleptic complexes have exhibited interesting metal–ligand redox interplay as a result of the redox-active or non-innocent nature of dithiolene ligands (Chandrasekaran et al., 2014). In this context, phosphine-induced cleavage of the iron and cobalt bis(dithiolene) dimer to yield five-coordinate bis(dithiolene)phosphine has been explored in depth with PPh3 and PMe3 ligands (Selby-Karney et al., 2017; Yu et al., 2007). These complexes were all synthesized from the corresponding bis(dithiolene) metal dimer complexes followed by addition of an excess of phosphine ligand to form bis(dithiolene) metal complexes bound to an additional phosphine ligand. The resulting [M(adt)2(PR3)] (M = Co, Fe; adt = para-anisylphenyldithiolene; PR3 = PMe3 or PPh3) complexes have approximately square-pyramidal geometries at the metal center.
Herein, we report the synthesis and 2(PTA)] (pdt = phenyldithiolene, S2C2Ph2), produced by PTA ligand-induced cleavage of the cobalt bis(dithiolene) dimer [Co2(pdt)4].
of a five-coordinate cobalt dithiolene-phosphine complex [Co(pdt)2. Structural commentary
[Co(pdt)2(PTA)] co-crystallizes with one molecule of 1,2-dichloroethane where half of the solvent molecule is symmetry generated, as shown in Fig. 1. The structure without hydrogen atoms is depicted in Fig. 2 for clarity. Each dithiolene ligand coordinates to the cobalt center in a κ2 fashion via the sulfur atoms, and PTA coordinates via the apical phosphorous atom. The cobalt dithiolene core is approximately planar, with angles of 89.73 (2)° for S1—Co1—S2, 88.93 (2)° for S1—Co1—S3, 88.41 (2)° for S2—Co1—S4, and 89.90 (2)° for S3—Co1—S4. The sum of the angles is 356.97 (4)°, consistent with only a slight distortion from planarity. The PTA ligand occupies a 5th coordination site with angles of 101.94 (2)° for P1—Co1—S1, 98.12 (2)° for P1—Co1—S2, 90.97 (2)° for P1—Co1—S3, and 97.22 (2)° for P1–Co1—S4. Therefore, the overall geometry of [Co(pdt)2(PTA)] is approximately square pyramidal.
The distances from the cobalt atom to the sulfur ligands are 2.1620 (5) Å for Co1—S1, 2.1669 (6) Å for Co1—S2, 2.1685 (5) Å for Co1—S3, and 2.1487 (5) Å for Co1—S4. These are mostly within the range of Co—S distances of 2.1659 (9)–2.1765 (9) Å reported for the p-anisyl-substituted analogues with PMe3 and PPh3 (Selby-Karney et al., 2017; Yu et al., 2007). The Co1—P1 distance is 2.1424 (5) Å, which is shorter than the distances of 2.163 (1) and 2.192 (1) Å reported for the p-anisyl-substituted analogues with PMe3 and PPh3, respectively (Selby-Karney et al., 2017; Yu et al., 2007). The decreasing length of the Co1—P1 bond for PPh3 > PMe3 > PTA is not consistent with the σ-donating ability of the phosphine which increases from PPh3 < PTA < PMe3. Instead, the short Co1—P1 bond for [Co(pdt)2(PTA)] is attributed to the small cone angle of 103° (Phillips et al., 2004) as compared to the cone angle of 118° for PMe3 and 145° for PPh3 (Bilbrey et al., 2013).
The sulfur–carbon distances are consistent with a partially reduced ligand thienyl radical monoanion with distances of 1.728 (2) Å for S1—C7, 1.719 (2) Å for S2—C8, 1.729 (2) Å for S3—C21, and 1.731 (2) Å for S4—C22. These are mostly within the range of S—C distances of 1.721 (2)–1.726 (3) and 1.730 (3)–1.742 (3) Å reported for the p-anisyl-substituted analogues with PMe3 and PPh3, respectively (Selby-Karney et al., 2017; Yu et al., 2007). The C7—C8 distance of 1.372 (3) Å and the C21—C22 distance of 1.365 (3) Å are also consistent with this description.
3. Supramolecular features
Two molecules of [Co(pdt)2(PTA)] and one molecule of 1,2-dicholorethane are present in the as depicted in Fig. 3. The two metal complexes in the are related by an inversion operation with the inversion center on the 1,2-dichloroethane and the cobalt dithiolene cores being approximately parallel to each other. Six close contacts within the supramolecular framework were identified (Fig. 3, Table 1), resulting primarily from hydrogen-bonding interactions with nitrogen, sulfur and chlorine. Hydrogen bonds with sulfur and nitrogen include the C19—H19⋯S4ii distance of 2.78 Å (Figs. 3, #2) and the C35—H35a⋯N2 distance of 2.69 Å (Figs. 3, #4). Weaker hydrogen bonds with chlorine include the C2—H2a⋯Cl1iii distance of 2.88 Å (Figs. 3, #3) and the C26—H26⋯Cl1iv distance of 2.95 Å (Figs. 3, #5). Close contacts with carbon and hydrogen atoms include a C28—H28⋯C11i distance of 2.83 Å (Figs. 3, #1; see Table 1 for symmetry operators).
When the b axis, parallel displaced π-stacking of the aryl rings is revealed (Fig. 4). Planes defined by atoms C15–C20 (Fig. 4, blue) and C15v–C20v [Fig. 4, purple; symmetry code: (v) 1 − x, −y, 1 − z] within the are parallel, with a distance of 2.928 Å between planes and a distance of 4.961 Å between the respective centroids defined by the same atoms. The shortest atomic distance is between the carbon atoms of the aryl rings between unit cells with C17⋯C18v being 3.343 (3) Å apart (Figs. 3, #6; Fig. 4).
is grown along the4. Database survey
A survey of the Cambridge Structural Database (Web accessed March 26, 2020; Groom et al., 2016) and SciFinder (SciFinder, 2020) yielded no exact matches for reported structures of this complex. Structures with two dithiolene ligands with p-anisyl substitution bound to Co and an additional coordinated phosphine ligand were reported with PMe3 coordination (Selby-Karney et al., 2017), and PPh3 coordination (Yu et al., 2007). Both reported complexes also have approximately square pyramidal geometry at the cobalt center with slight deviations. The PPh3 complex exhibits the largest distortion from planarity with a sum of angles around cobalt of 353.89 (6)°, while the sum of the angles is 356.97 (6)° for the PMe3 complex. Similarly, the phosphine in PPh3 is axially distorted because of the steric bulk of the phenyl groups, resulting in two more obtuse bond angles for S2—Co1—P1 and S3—Co1—P1 of 101.31 (3) and 106.6 (3)°, respectively. The other bond angles of 92.81 (3)° for S1—Co1–P1 and 97.13 (3)° for S4—Co1—P1 are within the range of S—Co1—P1 angles of 91.19 (3) to 99.65 (3)° observed for the PMe3 complex.
5. Spectroscopic analysis
The UV–vis characterization of [Co(pdt)2(PTA)] was conducted in dichloromethane (Fig. 5) and revealed a strong absorption at 877 nm with a molar absorptivitiy of 6428 M−1cm−1. In the related p-anisyl-substituted cobalt complex bound to PMe3 a similar absorption was observed at 905 nm. This is attributed to a ligand-to-ligand charge-transfer (LLCT) transition, based on comparison with the related iron complex with PPh3 (Yu et al., 2007) and related dithiolene metal complexes (Ray et al., 2005). In the iron PPh3 complex, the absorption occurred at 720 nm and disappeared upon conversion to the homoleptic iron bis(dithiolene) complex. The IR signal for [Co(pdt)2(PTA)] at 1157.61 cm−1 is characteristic of monoanionic dithiolenes with a π-radical when coordinated to metals, and is attributed to ν(C=S·) (Patra et al., 2006). Combined, the IR and UV–vis characterization are consistent with two monoanionic dithiolene ligands bound to a CoII center.
6. Electrochemical analysis
The cyclic voltammogram (CV) of [Co(pdt)2(PTA)] was collected in a solution of dichoromethane with a platinum (Fig. 6) and a glassy carbon (Fig. 7). Both CVs display two reversible waves with the first one at E1/2 = +0.62 with both electrodes, and a second one at E1/2 = −0.17 V with the platinum electrode and E1/2 = −0.16 V with the glassy The reversible oxidation wave at +0.62 V is attributed to a metal-centered redox event. The second oxidation at −0.17 V is attributed to ligand oxidation, by comparison to other metal dithiolene complexes (Patra et al., 2006).
7. Synthesis and crystallization
A 50 mL Schlenk flask containing a stir bar was charged with [Co2(pdt)4] (0.300 g, 0.275 mmol) and PTA (0.144 g; 0.551 mmol) under an N2 atmosphere. To this mixture of solids, 20 mL of CH2Cl2 were added and stirred for 4 h at room temperature. The solvent was removed under reduced pressure and the resulting dark-orange solid was washed with 3 × 5 mL of Et2O and dried under vacuum. The product was stable under reduced pressure and at room temperature. Yield: 92% (0.357 g, 0.509 mmol). Crystals suitable for X-ray diffraction were grown by the vapor diffusion method with diffusion of pentane over a 1,2-dichloroethane solution of the compound. UV–Vis spectra were obtained at ambient temperature with a Varian Cary 50 diode array spectrometer, while IR spectra were taken neat with an ALPHA FTIR instrument. Electrochemical measurements were performed with a CHI600E electroanalyzer workstation using an Ag/AgCl a platinum disk a platinum wire and [nBu4N][PF6] as the in CH2Cl2. Under these conditions, the [Cp2Fe]+/ Cp2Fe couple consistently occurred at +440 mV. UV–vis in CH2Cl2: [λmax, nm (∊M, M−1cm−1)]: 301 nm (17881), 877 nm (6428). IR spectroscopy (cm−1): 3366.53 (w), 3054.34 (w), 2928.02 (w), 2869.68 (w), 1592.50 (w), 1440.63 (m), 1415.07 (s), 1275.25 (m), 1240.54 (w), 1157.61 (m), 1091.56 (s), 1012.49 (m), 969.10 (s), 940.65 (vs), 739.50 (s), 693.31 (s).
8. Refinement
Crystal data, data collection and structure . Hydrogen atoms were placed in calculated positions with C—H distances of 0.95 and 0.99 Å for CH and CH2, respectively, and refined using a riding model with Uiso(H) = 1.2 Ueq(C) for CH and CH2.
details are summarized in Table 2
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Supporting information
CCDC reference: 1986931
https://doi.org/10.1107/S2056989020005447/zl2776sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989020005447/zl2776Isup2.hkl
Data collection: APEX3 (Bruker, 2017); cell
SAINT (Bruker, 2017); data reduction: SAINT (Bruker, 2017); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: OLEX2 (Dolomanov et al., 2009) and SHELXL2017 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2020); software used to prepare material for publication: publCIF (Westrip, 2010).[Co(C14H10S2)2(C6H12N3P)·0.5C2H4Cl2 | Z = 2 |
Mr = 750.24 | F(000) = 776 |
Triclinic, P1 | Dx = 1.467 Mg m−3 |
a = 9.0954 (7) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 13.4319 (9) Å | Cell parameters from 9901 reflections |
c = 14.7905 (10) Å | θ = 3.5–34.9° |
α = 97.074 (3)° | µ = 0.91 mm−1 |
β = 94.680 (3)° | T = 113 K |
γ = 107.354 (3)° | Prism, black |
V = 1698.1 (2) Å3 | 0.57 × 0.32 × 0.14 mm |
Bruker D8 Venture Kappa diffractometer | 6778 reflections with I > 2σ(I) |
Radiation source: microfocus sealed tube | Rint = 0.045 |
φ and ω scans | θmax = 27.1°, θmin = 2.6° |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −11→11 |
Tmin = 0.661, Tmax = 0.746 | k = −17→17 |
46909 measured reflections | l = −18→18 |
7487 independent 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)] = 0.031 | Hydrogen site location: mixed |
wR(F2) = 0.083 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0327P)2 + 1.8472P] where P = (Fo2 + 2Fc2)/3 |
7487 reflections | (Δ/σ)max = 0.002 |
406 parameters | Δρmax = 0.73 e Å−3 |
0 restraints | Δρmin = −0.40 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.2841 (2) | 0.44175 (16) | 0.13148 (14) | 0.0238 (4) | |
H1A | 0.327954 | 0.444029 | 0.072381 | 0.029* | |
H1B | 0.262644 | 0.369103 | 0.145884 | 0.029* | |
Co1 | 0.64640 (3) | 0.50794 (2) | 0.24515 (2) | 0.01404 (7) | |
N1 | 0.1384 (2) | 0.46794 (14) | 0.12245 (13) | 0.0265 (4) | |
Cl1 | −0.03998 (7) | 0.64232 (4) | 0.56103 (4) | 0.03132 (12) | |
S1 | 0.59835 (5) | 0.34986 (3) | 0.17196 (3) | 0.01709 (10) | |
P1 | 0.42620 (5) | 0.53418 (4) | 0.22219 (3) | 0.01466 (10) | |
C2 | 0.3048 (2) | 0.52908 (19) | 0.31626 (14) | 0.0262 (4) | |
H2A | 0.284600 | 0.459895 | 0.337846 | 0.031* | |
H2B | 0.360251 | 0.584927 | 0.368404 | 0.031* | |
S2 | 0.61456 (5) | 0.44452 (3) | 0.37252 (3) | 0.01757 (10) | |
N2 | 0.1566 (2) | 0.54440 (16) | 0.28436 (13) | 0.0279 (4) | |
C3 | 0.0688 (2) | 0.46267 (18) | 0.20808 (17) | 0.0319 (5) | |
H3A | 0.058232 | 0.392641 | 0.226358 | 0.038* | |
H3B | −0.036915 | 0.468504 | 0.196775 | 0.038* | |
S3 | 0.71513 (5) | 0.56935 (3) | 0.12089 (3) | 0.01568 (10) | |
N3 | 0.25473 (19) | 0.65989 (13) | 0.17147 (12) | 0.0225 (3) | |
C4 | 0.1799 (2) | 0.64750 (18) | 0.25548 (15) | 0.0276 (4) | |
H4A | 0.244268 | 0.702669 | 0.305799 | 0.033* | |
H4B | 0.077805 | 0.659288 | 0.245456 | 0.033* | |
S4 | 0.76992 (5) | 0.65936 (3) | 0.32479 (3) | 0.01744 (10) | |
C20 | 0.4388 (3) | 0.24991 (15) | 0.47931 (13) | 0.0238 (4) | |
H20 | 0.373511 | 0.292452 | 0.470978 | 0.029* | |
C21 | 0.8023 (2) | 0.70357 (14) | 0.15445 (13) | 0.0156 (3) | |
C22 | 0.8262 (2) | 0.74384 (14) | 0.24571 (12) | 0.0150 (3) | |
C23 | 0.8953 (2) | 0.85744 (14) | 0.28453 (13) | 0.0169 (3) | |
C24 | 1.0120 (2) | 0.88975 (16) | 0.35854 (15) | 0.0265 (4) | |
H24 | 1.051162 | 0.839134 | 0.382873 | 0.032* | |
C25 | 1.0716 (3) | 0.99529 (17) | 0.39707 (17) | 0.0330 (5) | |
H25 | 1.151905 | 1.016440 | 0.447350 | 0.040* | |
C26 | 1.0157 (3) | 1.06997 (16) | 0.36321 (16) | 0.0291 (5) | |
H26 | 1.057262 | 1.142228 | 0.389814 | 0.035* | |
C27 | 0.8984 (3) | 1.03871 (16) | 0.29017 (15) | 0.0279 (4) | |
H27 | 0.858604 | 1.089600 | 0.266868 | 0.033* | |
C28 | 0.8388 (2) | 0.93339 (16) | 0.25086 (14) | 0.0228 (4) | |
H28 | 0.758727 | 0.912696 | 0.200497 | 0.027* | |
C29 | 0.8531 (2) | 0.76591 (14) | 0.07994 (12) | 0.0159 (3) | |
C30 | 0.7460 (2) | 0.78816 (16) | 0.01894 (14) | 0.0229 (4) | |
H30 | 0.638499 | 0.763550 | 0.025136 | 0.027* | |
C31 | 0.7949 (3) | 0.84572 (17) | −0.05041 (14) | 0.0293 (5) | |
H31 | 0.721373 | 0.861822 | −0.090688 | 0.035* | |
C32 | 0.9510 (3) | 0.87993 (17) | −0.06125 (15) | 0.0300 (5) | |
H32 | 0.984506 | 0.918433 | −0.109521 | 0.036* | |
C33 | 1.0578 (3) | 0.85777 (18) | −0.00151 (16) | 0.0311 (5) | |
H33 | 1.164953 | 0.881375 | −0.008711 | 0.037* | |
C34 | 1.0094 (2) | 0.80118 (16) | 0.06902 (14) | 0.0240 (4) | |
H34 | 1.083649 | 0.786567 | 0.109948 | 0.029* | |
C35 | 0.0253 (2) | 0.55372 (15) | 0.48550 (14) | 0.0226 (4) | |
H35A | −0.019761 | 0.549633 | 0.421409 | 0.027* | |
H35B | 0.139845 | 0.579612 | 0.488730 | 0.027* | |
C5 | 0.1638 (2) | 0.57416 (17) | 0.09845 (14) | 0.0252 (4) | |
H5A | 0.217909 | 0.579321 | 0.042966 | 0.030* | |
H5B | 0.061620 | 0.584021 | 0.082845 | 0.030* | |
C8 | 0.5691 (2) | 0.30997 (14) | 0.34348 (13) | 0.0173 (4) | |
C7 | 0.5610 (2) | 0.26674 (14) | 0.25345 (13) | 0.0173 (4) | |
C6 | 0.4165 (2) | 0.65983 (16) | 0.18756 (15) | 0.0232 (4) | |
H6A | 0.474959 | 0.719078 | 0.236339 | 0.028* | |
H6B | 0.465750 | 0.670512 | 0.130753 | 0.028* | |
C9 | 0.5189 (2) | 0.15214 (14) | 0.21930 (13) | 0.0183 (4) | |
C19 | 0.4218 (3) | 0.18900 (17) | 0.54991 (15) | 0.0341 (5) | |
H19 | 0.342685 | 0.188436 | 0.588150 | 0.041* | |
C10 | 0.5971 (2) | 0.11500 (15) | 0.15203 (14) | 0.0215 (4) | |
H10 | 0.680174 | 0.163381 | 0.129720 | 0.026* | |
C11 | 0.5548 (3) | 0.00803 (16) | 0.11733 (14) | 0.0252 (4) | |
H11 | 0.608667 | −0.016269 | 0.071427 | 0.030* | |
C12 | 0.4341 (3) | −0.06324 (16) | 0.14966 (15) | 0.0273 (4) | |
H12 | 0.405635 | −0.136409 | 0.126284 | 0.033* | |
C14 | 0.3962 (2) | 0.07902 (15) | 0.25086 (13) | 0.0216 (4) | |
H14 | 0.340984 | 0.102673 | 0.296318 | 0.026* | |
C13 | 0.3552 (2) | −0.02763 (16) | 0.21590 (14) | 0.0260 (4) | |
H13 | 0.272179 | −0.076569 | 0.237726 | 0.031* | |
C15 | 0.5509 (2) | 0.24862 (14) | 0.42110 (13) | 0.0190 (4) | |
C16 | 0.6491 (2) | 0.18828 (16) | 0.43625 (15) | 0.0268 (4) | |
H16 | 0.726843 | 0.187116 | 0.397345 | 0.032* | |
C17 | 0.6331 (3) | 0.12979 (17) | 0.50830 (17) | 0.0356 (6) | |
H17 | 0.701147 | 0.089642 | 0.518871 | 0.043* | |
C18 | 0.5191 (3) | 0.12967 (17) | 0.56452 (15) | 0.0367 (6) | |
H18 | 0.507881 | 0.088833 | 0.613074 | 0.044* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0212 (10) | 0.0219 (10) | 0.0265 (10) | 0.0092 (8) | −0.0051 (8) | −0.0047 (8) |
Co1 | 0.01191 (12) | 0.01288 (12) | 0.01779 (13) | 0.00396 (9) | 0.00186 (9) | 0.00394 (9) |
N1 | 0.0189 (8) | 0.0249 (9) | 0.0342 (10) | 0.0091 (7) | −0.0055 (7) | −0.0012 (7) |
Cl1 | 0.0363 (3) | 0.0239 (2) | 0.0365 (3) | 0.0108 (2) | 0.0142 (2) | 0.0052 (2) |
S1 | 0.0180 (2) | 0.0140 (2) | 0.0196 (2) | 0.00467 (17) | 0.00375 (16) | 0.00368 (16) |
P1 | 0.0124 (2) | 0.0152 (2) | 0.0172 (2) | 0.00534 (17) | 0.00227 (16) | 0.00254 (17) |
C2 | 0.0196 (10) | 0.0406 (12) | 0.0239 (10) | 0.0142 (9) | 0.0075 (8) | 0.0103 (9) |
S2 | 0.0199 (2) | 0.0142 (2) | 0.0185 (2) | 0.00479 (17) | 0.00112 (16) | 0.00396 (16) |
N2 | 0.0189 (8) | 0.0421 (11) | 0.0296 (9) | 0.0159 (8) | 0.0089 (7) | 0.0117 (8) |
C3 | 0.0133 (9) | 0.0310 (11) | 0.0524 (14) | 0.0047 (8) | 0.0036 (9) | 0.0160 (10) |
S3 | 0.0155 (2) | 0.0135 (2) | 0.0172 (2) | 0.00298 (16) | 0.00296 (16) | 0.00246 (16) |
N3 | 0.0173 (8) | 0.0213 (8) | 0.0319 (9) | 0.0101 (7) | 0.0027 (7) | 0.0054 (7) |
C4 | 0.0239 (10) | 0.0323 (11) | 0.0301 (11) | 0.0168 (9) | 0.0034 (8) | −0.0021 (9) |
S4 | 0.0192 (2) | 0.0150 (2) | 0.0166 (2) | 0.00298 (17) | 0.00080 (16) | 0.00396 (16) |
C20 | 0.0338 (11) | 0.0164 (9) | 0.0207 (9) | 0.0071 (8) | 0.0032 (8) | 0.0027 (7) |
C21 | 0.0110 (8) | 0.0146 (8) | 0.0216 (9) | 0.0036 (6) | 0.0026 (6) | 0.0051 (7) |
C22 | 0.0114 (8) | 0.0152 (8) | 0.0195 (8) | 0.0049 (7) | 0.0010 (6) | 0.0062 (7) |
C23 | 0.0160 (8) | 0.0154 (8) | 0.0196 (9) | 0.0047 (7) | 0.0046 (7) | 0.0031 (7) |
C24 | 0.0269 (11) | 0.0174 (9) | 0.0332 (11) | 0.0077 (8) | −0.0063 (8) | 0.0012 (8) |
C25 | 0.0308 (12) | 0.0231 (11) | 0.0394 (12) | 0.0082 (9) | −0.0120 (9) | −0.0053 (9) |
C26 | 0.0332 (12) | 0.0160 (9) | 0.0352 (12) | 0.0065 (8) | 0.0022 (9) | −0.0030 (8) |
C27 | 0.0390 (12) | 0.0203 (10) | 0.0285 (10) | 0.0154 (9) | 0.0035 (9) | 0.0043 (8) |
C28 | 0.0264 (10) | 0.0210 (9) | 0.0216 (9) | 0.0093 (8) | −0.0003 (8) | 0.0028 (7) |
C29 | 0.0183 (9) | 0.0123 (8) | 0.0166 (8) | 0.0043 (7) | 0.0022 (7) | 0.0016 (6) |
C30 | 0.0187 (9) | 0.0226 (10) | 0.0248 (10) | 0.0028 (8) | −0.0016 (7) | 0.0063 (8) |
C31 | 0.0363 (12) | 0.0249 (10) | 0.0236 (10) | 0.0059 (9) | −0.0063 (9) | 0.0072 (8) |
C32 | 0.0417 (13) | 0.0224 (10) | 0.0240 (10) | 0.0036 (9) | 0.0089 (9) | 0.0099 (8) |
C33 | 0.0280 (11) | 0.0315 (11) | 0.0359 (12) | 0.0067 (9) | 0.0150 (9) | 0.0125 (9) |
C34 | 0.0205 (10) | 0.0249 (10) | 0.0288 (10) | 0.0076 (8) | 0.0063 (8) | 0.0091 (8) |
C35 | 0.0228 (10) | 0.0240 (10) | 0.0227 (9) | 0.0088 (8) | 0.0051 (7) | 0.0046 (8) |
C5 | 0.0224 (10) | 0.0319 (11) | 0.0250 (10) | 0.0152 (9) | −0.0013 (8) | 0.0039 (8) |
C8 | 0.0125 (8) | 0.0162 (8) | 0.0234 (9) | 0.0038 (7) | 0.0010 (7) | 0.0061 (7) |
C7 | 0.0127 (8) | 0.0168 (9) | 0.0230 (9) | 0.0042 (7) | 0.0029 (7) | 0.0061 (7) |
C6 | 0.0177 (9) | 0.0201 (9) | 0.0355 (11) | 0.0091 (8) | 0.0042 (8) | 0.0093 (8) |
C9 | 0.0162 (9) | 0.0159 (9) | 0.0215 (9) | 0.0037 (7) | −0.0025 (7) | 0.0040 (7) |
C19 | 0.0601 (16) | 0.0197 (10) | 0.0189 (10) | 0.0064 (10) | 0.0093 (10) | 0.0010 (8) |
C10 | 0.0213 (9) | 0.0178 (9) | 0.0260 (10) | 0.0070 (7) | 0.0012 (7) | 0.0047 (7) |
C11 | 0.0294 (11) | 0.0217 (10) | 0.0260 (10) | 0.0123 (8) | −0.0012 (8) | 0.0020 (8) |
C12 | 0.0326 (11) | 0.0147 (9) | 0.0305 (11) | 0.0051 (8) | −0.0091 (9) | 0.0019 (8) |
C14 | 0.0208 (9) | 0.0193 (9) | 0.0221 (9) | 0.0029 (8) | −0.0011 (7) | 0.0044 (7) |
C13 | 0.0260 (10) | 0.0186 (9) | 0.0284 (10) | −0.0010 (8) | −0.0035 (8) | 0.0085 (8) |
C15 | 0.0210 (9) | 0.0131 (8) | 0.0194 (9) | 0.0017 (7) | −0.0033 (7) | 0.0027 (7) |
C16 | 0.0234 (10) | 0.0191 (9) | 0.0358 (11) | 0.0065 (8) | −0.0075 (8) | 0.0038 (8) |
C17 | 0.0423 (13) | 0.0186 (10) | 0.0405 (13) | 0.0081 (9) | −0.0213 (11) | 0.0045 (9) |
C18 | 0.0674 (17) | 0.0159 (10) | 0.0187 (10) | 0.0045 (10) | −0.0094 (10) | 0.0036 (8) |
C1—H1A | 0.9900 | C27—H27 | 0.9500 |
C1—H1B | 0.9900 | C27—C28 | 1.386 (3) |
C1—N1 | 1.469 (3) | C28—H28 | 0.9500 |
C1—P1 | 1.833 (2) | C29—C30 | 1.396 (3) |
Co1—S1 | 2.1620 (5) | C29—C34 | 1.388 (3) |
Co1—P1 | 2.1424 (5) | C30—H30 | 0.9500 |
Co1—S2 | 2.1669 (5) | C30—C31 | 1.383 (3) |
Co1—S3 | 2.1685 (5) | C31—H31 | 0.9500 |
Co1—S4 | 2.1487 (5) | C31—C32 | 1.385 (3) |
N1—C3 | 1.462 (3) | C32—H32 | 0.9500 |
N1—C5 | 1.469 (3) | C32—C33 | 1.382 (3) |
Cl1—C35 | 1.794 (2) | C33—H33 | 0.9500 |
S1—C7 | 1.7282 (18) | C33—C34 | 1.389 (3) |
P1—C2 | 1.841 (2) | C34—H34 | 0.9500 |
P1—C6 | 1.847 (2) | C35—C35i | 1.506 (4) |
C2—H2A | 0.9900 | C35—H35A | 0.9900 |
C2—H2B | 0.9900 | C35—H35B | 0.9900 |
C2—N2 | 1.472 (3) | C5—H5A | 0.9900 |
S2—C8 | 1.7192 (19) | C5—H5B | 0.9900 |
N2—C3 | 1.463 (3) | C8—C7 | 1.372 (3) |
N2—C4 | 1.460 (3) | C8—C15 | 1.486 (2) |
C3—H3A | 0.9900 | C7—C9 | 1.482 (3) |
C3—H3B | 0.9900 | C6—H6A | 0.9900 |
S3—C21 | 1.7286 (18) | C6—H6B | 0.9900 |
N3—C4 | 1.468 (3) | C9—C10 | 1.396 (3) |
N3—C5 | 1.468 (3) | C9—C14 | 1.405 (3) |
N3—C6 | 1.471 (2) | C19—H19 | 0.9500 |
C4—H4A | 0.9900 | C19—C18 | 1.377 (4) |
C4—H4B | 0.9900 | C10—H10 | 0.9500 |
S4—C22 | 1.7307 (18) | C10—C11 | 1.390 (3) |
C20—H20 | 0.9500 | C11—H11 | 0.9500 |
C20—C19 | 1.395 (3) | C11—C12 | 1.386 (3) |
C20—C15 | 1.390 (3) | C12—H12 | 0.9500 |
C21—C22 | 1.365 (3) | C12—C13 | 1.381 (3) |
C21—C29 | 1.486 (2) | C14—H14 | 0.9500 |
C22—C23 | 1.485 (2) | C14—C13 | 1.388 (3) |
C23—C24 | 1.390 (3) | C13—H13 | 0.9500 |
C23—C28 | 1.396 (3) | C15—C16 | 1.395 (3) |
C24—H24 | 0.9500 | C16—H16 | 0.9500 |
C24—C25 | 1.386 (3) | C16—C17 | 1.392 (3) |
C25—H25 | 0.9500 | C17—H17 | 0.9500 |
C25—C26 | 1.379 (3) | C17—C18 | 1.380 (4) |
C26—H26 | 0.9500 | C18—H18 | 0.9500 |
C26—C27 | 1.383 (3) | ||
H1A—C1—H1B | 108.0 | C27—C28—C23 | 120.67 (19) |
N1—C1—H1A | 109.4 | C27—C28—H28 | 119.7 |
N1—C1—H1B | 109.4 | C30—C29—C21 | 121.23 (17) |
N1—C1—P1 | 111.30 (13) | C34—C29—C21 | 119.85 (17) |
P1—C1—H1A | 109.4 | C34—C29—C30 | 118.91 (17) |
P1—C1—H1B | 109.4 | C29—C30—H30 | 119.7 |
S1—Co1—S2 | 89.729 (19) | C31—C30—C29 | 120.58 (19) |
S1—Co1—S3 | 88.927 (19) | C31—C30—H30 | 119.7 |
P1—Co1—S1 | 101.94 (2) | C30—C31—H31 | 119.9 |
P1—Co1—S2 | 98.12 (2) | C30—C31—C32 | 120.1 (2) |
P1—Co1—S3 | 90.975 (19) | C32—C31—H31 | 119.9 |
P1—Co1—S4 | 97.22 (2) | C31—C32—H32 | 120.2 |
S2—Co1—S3 | 170.88 (2) | C33—C32—C31 | 119.68 (19) |
S4—Co1—S1 | 160.81 (2) | C33—C32—H32 | 120.2 |
S4—Co1—S2 | 88.415 (19) | C32—C33—H33 | 119.8 |
S4—Co1—S3 | 89.895 (19) | C32—C33—C34 | 120.4 (2) |
C3—N1—C1 | 110.66 (17) | C34—C33—H33 | 119.8 |
C3—N1—C5 | 108.76 (17) | C29—C34—C33 | 120.29 (19) |
C5—N1—C1 | 111.36 (16) | C29—C34—H34 | 119.9 |
C7—S1—Co1 | 106.05 (7) | C33—C34—H34 | 119.9 |
C1—P1—Co1 | 116.49 (7) | Cl1—C35—H35A | 110.0 |
C1—P1—C2 | 99.60 (10) | Cl1—C35—H35B | 110.0 |
C1—P1—C6 | 99.16 (10) | C35i—C35—Cl1 | 108.53 (18) |
C2—P1—Co1 | 119.19 (7) | C35i—C35—H35A | 110.0 |
C2—P1—C6 | 98.56 (10) | C35i—C35—H35B | 110.0 |
C6—P1—Co1 | 119.84 (6) | H35A—C35—H35B | 108.4 |
P1—C2—H2A | 109.6 | N1—C5—H5A | 108.7 |
P1—C2—H2B | 109.6 | N1—C5—H5B | 108.7 |
H2A—C2—H2B | 108.2 | N3—C5—N1 | 114.18 (16) |
N2—C2—P1 | 110.06 (14) | N3—C5—H5A | 108.7 |
N2—C2—H2A | 109.6 | N3—C5—H5B | 108.7 |
N2—C2—H2B | 109.6 | H5A—C5—H5B | 107.6 |
C8—S2—Co1 | 105.84 (7) | C7—C8—S2 | 119.61 (14) |
C3—N2—C2 | 111.82 (17) | C7—C8—C15 | 124.29 (17) |
C4—N2—C2 | 111.77 (17) | C15—C8—S2 | 115.98 (14) |
C4—N2—C3 | 108.62 (17) | C8—C7—S1 | 118.77 (14) |
N1—C3—N2 | 114.42 (17) | C8—C7—C9 | 124.82 (17) |
N1—C3—H3A | 108.7 | C9—C7—S1 | 116.40 (14) |
N1—C3—H3B | 108.7 | P1—C6—H6A | 109.4 |
N2—C3—H3A | 108.7 | P1—C6—H6B | 109.4 |
N2—C3—H3B | 108.7 | N3—C6—P1 | 111.14 (13) |
H3A—C3—H3B | 107.6 | N3—C6—H6A | 109.4 |
C21—S3—Co1 | 105.31 (6) | N3—C6—H6B | 109.4 |
C4—N3—C6 | 110.70 (16) | H6A—C6—H6B | 108.0 |
C5—N3—C4 | 108.50 (16) | C10—C9—C7 | 120.40 (17) |
C5—N3—C6 | 111.41 (16) | C10—C9—C14 | 118.51 (18) |
N2—C4—N3 | 114.23 (16) | C14—C9—C7 | 121.05 (17) |
N2—C4—H4A | 108.7 | C20—C19—H19 | 119.8 |
N2—C4—H4B | 108.7 | C18—C19—C20 | 120.4 (2) |
N3—C4—H4A | 108.7 | C18—C19—H19 | 119.8 |
N3—C4—H4B | 108.7 | C9—C10—H10 | 119.6 |
H4A—C4—H4B | 107.6 | C11—C10—C9 | 120.75 (19) |
C22—S4—Co1 | 105.61 (6) | C11—C10—H10 | 119.6 |
C19—C20—H20 | 119.9 | C10—C11—H11 | 120.0 |
C15—C20—H20 | 119.9 | C12—C11—C10 | 120.1 (2) |
C15—C20—C19 | 120.3 (2) | C12—C11—H11 | 120.0 |
C22—C21—S3 | 119.00 (13) | C11—C12—H12 | 120.1 |
C22—C21—C29 | 124.87 (16) | C13—C12—C11 | 119.86 (19) |
C29—C21—S3 | 116.05 (13) | C13—C12—H12 | 120.1 |
C21—C22—S4 | 119.29 (14) | C9—C14—H14 | 119.9 |
C21—C22—C23 | 125.07 (16) | C13—C14—C9 | 120.25 (19) |
C23—C22—S4 | 115.62 (13) | C13—C14—H14 | 119.9 |
C24—C23—C22 | 120.60 (17) | C12—C13—C14 | 120.58 (19) |
C24—C23—C28 | 118.51 (18) | C12—C13—H13 | 119.7 |
C28—C23—C22 | 120.80 (17) | C14—C13—H13 | 119.7 |
C23—C24—H24 | 119.8 | C20—C15—C8 | 121.69 (17) |
C25—C24—C23 | 120.45 (19) | C20—C15—C16 | 119.03 (18) |
C25—C24—H24 | 119.8 | C16—C15—C8 | 119.29 (18) |
C24—C25—H25 | 119.6 | C15—C16—H16 | 120.0 |
C26—C25—C24 | 120.7 (2) | C17—C16—C15 | 120.1 (2) |
C26—C25—H25 | 119.6 | C17—C16—H16 | 120.0 |
C25—C26—H26 | 120.3 | C16—C17—H17 | 119.7 |
C25—C26—C27 | 119.41 (19) | C18—C17—C16 | 120.5 (2) |
C27—C26—H26 | 120.3 | C18—C17—H17 | 119.7 |
C26—C27—H27 | 119.9 | C19—C18—C17 | 119.7 (2) |
C26—C27—C28 | 120.24 (19) | C19—C18—H18 | 120.1 |
C28—C27—H27 | 119.9 | C17—C18—H18 | 120.1 |
C23—C28—H28 | 119.7 | ||
C1—N1—C3—N2 | 68.0 (2) | C21—C29—C34—C33 | 178.76 (19) |
C1—N1—C5—N3 | −67.8 (2) | C22—C21—C29—C30 | −108.8 (2) |
C1—P1—C2—N2 | −49.64 (17) | C22—C21—C29—C34 | 72.5 (2) |
C1—P1—C6—N3 | 49.67 (16) | C22—C23—C24—C25 | −177.3 (2) |
Co1—S1—C7—C8 | −0.88 (16) | C22—C23—C28—C27 | 176.84 (19) |
Co1—S1—C7—C9 | 177.96 (12) | C23—C24—C25—C26 | 0.5 (4) |
Co1—P1—C2—N2 | −177.43 (12) | C24—C23—C28—C27 | 0.3 (3) |
Co1—P1—C6—N3 | 177.50 (11) | C24—C25—C26—C27 | 0.2 (4) |
Co1—S2—C8—C7 | 0.23 (16) | C25—C26—C27—C28 | −0.6 (3) |
Co1—S2—C8—C15 | 176.41 (12) | C26—C27—C28—C23 | 0.4 (3) |
Co1—S3—C21—C22 | 6.17 (16) | C28—C23—C24—C25 | −0.7 (3) |
Co1—S3—C21—C29 | −176.88 (12) | C29—C21—C22—S4 | −176.22 (14) |
Co1—S4—C22—C21 | −6.88 (16) | C29—C21—C22—C23 | 5.2 (3) |
Co1—S4—C22—C23 | 171.84 (12) | C29—C30—C31—C32 | 1.4 (3) |
N1—C1—P1—Co1 | 179.98 (12) | C30—C29—C34—C33 | 0.1 (3) |
N1—C1—P1—C2 | 50.42 (17) | C30—C31—C32—C33 | −1.1 (3) |
N1—C1—P1—C6 | −49.96 (16) | C31—C32—C33—C34 | 0.2 (3) |
S1—C7—C9—C10 | 41.3 (2) | C32—C33—C34—C29 | 0.3 (3) |
S1—C7—C9—C14 | −136.15 (16) | C34—C29—C30—C31 | −0.9 (3) |
P1—C1—N1—C3 | −60.4 (2) | C5—N1—C3—N2 | −54.7 (2) |
P1—C1—N1—C5 | 60.7 (2) | C5—N3—C4—N2 | 55.1 (2) |
P1—C2—N2—C3 | 60.2 (2) | C5—N3—C6—P1 | −59.98 (19) |
P1—C2—N2—C4 | −61.8 (2) | C8—C7—C9—C10 | −140.0 (2) |
C2—P1—C6—N3 | −51.58 (16) | C8—C7—C9—C14 | 42.6 (3) |
C2—N2—C3—N1 | −68.7 (2) | C8—C15—C16—C17 | −179.60 (18) |
C2—N2—C4—N3 | 68.5 (2) | C7—C8—C15—C20 | −123.2 (2) |
S2—C8—C7—S1 | 0.4 (2) | C7—C8—C15—C16 | 57.0 (3) |
S2—C8—C7—C9 | −178.29 (14) | C7—C9—C10—C11 | −177.73 (18) |
S2—C8—C15—C20 | 60.8 (2) | C7—C9—C14—C13 | 177.89 (18) |
S2—C8—C15—C16 | −119.02 (17) | C6—P1—C2—N2 | 51.23 (17) |
C3—N1—C5—N3 | 54.4 (2) | C6—N3—C4—N2 | −67.4 (2) |
C3—N2—C4—N3 | −55.3 (2) | C6—N3—C5—N1 | 67.6 (2) |
S3—C21—C22—S4 | 0.4 (2) | C9—C10—C11—C12 | −0.2 (3) |
S3—C21—C22—C23 | −178.16 (14) | C9—C14—C13—C12 | −0.1 (3) |
S3—C21—C29—C30 | 74.4 (2) | C19—C20—C15—C8 | 178.12 (18) |
S3—C21—C29—C34 | −104.22 (18) | C19—C20—C15—C16 | −2.0 (3) |
C4—N2—C3—N1 | 55.1 (2) | C10—C9—C14—C13 | 0.4 (3) |
C4—N3—C5—N1 | −54.5 (2) | C10—C11—C12—C13 | 0.5 (3) |
C4—N3—C6—P1 | 60.85 (19) | C11—C12—C13—C14 | −0.3 (3) |
S4—C22—C23—C24 | 48.6 (2) | C14—C9—C10—C11 | −0.2 (3) |
S4—C22—C23—C28 | −127.87 (17) | C15—C20—C19—C18 | 2.1 (3) |
C20—C19—C18—C17 | −0.6 (3) | C15—C8—C7—S1 | −175.40 (14) |
C20—C15—C16—C17 | 0.5 (3) | C15—C8—C7—C9 | 5.9 (3) |
C21—C22—C23—C24 | −132.7 (2) | C15—C16—C17—C18 | 0.9 (3) |
C21—C22—C23—C28 | 50.8 (3) | C16—C17—C18—C19 | −0.9 (3) |
C21—C29—C30—C31 | −179.60 (18) |
Symmetry code: (i) −x, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C28—H28···C11ii | 0.95 | 2.83 | 3.575 (3) | 136 |
C19—H19···S4iii | 0.95 | 2.78 | 3.513 (3) | 135 |
C2—H2a···Cl1i | 0.99 | 2.88 | 3.582 (2) | 129 |
C35—H35a···N2 | 0.99 | 2.69 | 3.297 (3) | 120 |
C26—H26···Cl1iv | 0.95 | 2.95 | 3.824 (2) | 154 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x, y+1, z; (iii) −x+1, −y+1, −z+1; (iv) −x+1, −y+2, −z+1. |
Funding information
Funding for this research was provided by: National Science Foundation, Directorate for Mathematical and Physical Sciences (grant No. 1847926 to S. Chantal E. Stieber); U.S. Department of Defense, U.S. Army (grant No. W911NF-17-1-0537 to S. Chantal E. Stieber); MENTORES PPOHA (scholarship to Jacob P. Brannon); Lamar University [the Welch Foundation (V-0004) award to Perumalreddy Chandrasekaran].
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