metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2414-3146

Bis(4′-chloro-2,2′:6′,2′′-terpyridine-κ3N,N′,N′′)zinc(II) bis­­(tri­fluoro­methane­sulfonate)

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aDepartment of Chemistry and Biochemistry, University of the Incarnate Word, San Antonio, Texas 78209, USA, and bDepartment of Chemistry, The University of Texas at San Antonio, San Antonio, Texas 78249, USA
*Correspondence e-mail: adrian@uiwtx.edu

Edited by L. Van Meervelt, Katholieke Universiteit Leuven, Belgium (Received 12 November 2022; accepted 15 November 2022; online 24 November 2022)

In the title complex, [Zn(C15H10ClN3)2](CF3SO3)2, the ZnII metal center is sixfold coordinated by three nitro­gen atoms of each 4-chloro­terpyridine ligand in a distorted octa­hedral geometry with triflouro­methane­sulfonate ions completing the outer coordination sphere of the complex. ππ stacking inter­actions between the pyridyl rings in adjacent mol­ecules contribute to the alignment of the complexes in layers along the c axis.

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

Terpyridine and its substituted derivatives continue to be versatile chelating ligands with several applications in areas as diverse as catalysis (Rupp et al., 2019[Rupp, M., Auvray, T., Rousset, E., Mercier, G. M., Marvaud, V., Kurth, D. G. & Hanan, G. S. (2019). Inorg. Chem. 58, 9127-9134.]; Kobayashi & Nakazawa, 2021[Kobayashi, K. & Nakazawa, H. (2021). Chem. Asian J. 16, 3695-3701.]), supra­molecular design (Kuai et al., 2019[Kuai, Y., Li, W., Dong, Y., Wong, W. Y., Yan, S., Dai, Y. & Zhang, C. (2019). Dalton Trans. 48, 15121-15126.]; Ma et al., 2021[Ma, J., Lu, T., Duan, X., Xu, Y., Li, Z., Li, K., Shi, J., Bai, Q., Zhang, Z., Hao, X.-Q., Chen, Z., Wang, P. & Wang, M. (2021). Commun. Chem. 4, article number: 136 (2021).]), and drug design (Qin et al., 2019[Qin, Q. P., Wang, Z. F., Wang, S. L., Luo, D. M., Zou, B. Q., Yao, P. F., Tan, M. X. & Liang, H. (2019). Eur. J. Med. Chem. 170, 195-202.]; Savic et al., 2020[Savic, M., Arsenijevic, A., Milovanovic, J., Stojanovic, B., Stankovic, V., Rilak Simovic, A., Lazic, D., Arsenijevic, N. & Milovanovic, M. (2020). Molecules, 25, 4699.]). Recently, zinc(II) terpyridine complexes with phenyl-based substituents in the 4′-position of the terpyridine ring have shown excellent anti­cancer activity against several human carcinoma cell lines (Li et al., 2019[Li, J., Liu, R., Jiang, J., Liang, X., Huang, L., Huang, G., Chen, H., Pan, L. & Ma, Z. (2019). Molecules, 24, 4519.]). Our research group inter­est currently lies in synthesizing metal complexes with applications in biological systems; as part of our research in this area, herein, we describe the synthesis and structure of the title zinc(II) complex.

The asymmetric unit of the title complex shows the 4-chloro­terpyridine ligands surrounding the zinc metal center, with two tri­fluoro­sulfonate ions in the outer coord­ination sphere. The zinc(II) atom lies in an octa­hedral geometry defined by six pyridine nitro­gen atoms from the two 4-chloro­terpyridine ligands (Fig. 1[link]). All the Zn—N bond distances are in good agreement with comparable bis­(4-chloro­terpyridine)­zinc(II) complexes currently available in the Cambridge Structural Database (CSD, Groom et al., 2016[Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171-179.]; version 5.43 with update June 2022; refcodes MOZHAL and MOZHEP; You et al., 2009[You, W., Huang, W., Fan, Y. & Yao, C. (2009). J. Coord. Chem. 62, 2125-2137.]), but differ, by more than 0.1 Å in most cases, from those observed in complexes where only one 4-chloro­terpyridine is coordinated to the zinc(II) metal center (Adrian & Arman, 2020[Adrian, R. A. & Arman, H. D. (2020). IUCrData, 5, x201292.]; refcode JABDID; Adrian et al., 2020[Adrian, R. A., Canales, D. & Arman, H. D. (2020). IUCrData, 5, x201344.]; refcode PADBUV; Huang & Qian, 2008[Huang, W. & Qian, H. (2008). J. Mol. Struct. 874, 64-76.]; refcode HIVPOS; Dutta et al., 2019[Dutta, B., Das, D., Datta, J., Chandra, A., Jana, S., Sinha, C., Ray, P. P. & Mir, M. H. (2019). Inorg. Chem. Front. 6, 1245-1252.]; refcode DOHJES). The N—Zn—N angles also concur with the values reported in the previously referenced bis(4-chloroterpyridine)zinc(II) complexes. All relevant bonds and angles are presented in Table 1[link].

Table 1
Selected geometric parameters (Å, °)

Zn1—N4 2.109 (5) Zn1—N5 2.181 (6)
Zn1—N1 2.079 (5) Zn1—N6 2.163 (6)
Zn1—N3 2.196 (6) Zn1—N2 2.194 (6)
       
N4—Zn1—N3 106.9 (2) N1—Zn1—N2 75.1 (2)
N4—Zn1—N5 74.8 (2) N5—Zn1—N3 93.6 (2)
N4—Zn1—N6 75.1 (2) N5—Zn1—N2 94.0 (2)
N4—Zn1—N2 102.3 (2) N6—Zn1—N3 95.9 (2)
N1—Zn1—N4 177.4 (2) N6—Zn1—N5 149.97 (18)
N1—Zn1—N3 75.7 (2) N6—Zn1—N2 91.3 (2)
N1—Zn1—N5 105.4 (2) N2—Zn1—N3 150.86 (18)
N1—Zn1—N6 104.5 (2)    
[Figure 1]
Figure 1
The mol­ecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level; H atoms are omitted for clarity.

The packing diagram reveals the stacking of the asymmetric unit in alternating layers along the c axis (Fig. 2[link]). ππ stacking inter­actions occur between the N5 and N6 pyridyl rings of adjacent mol­ecules, with a centroid-to-centroid (Cg⋯Cg) distance of 3.826 (4) Å and an offset distance of 1.379 (10) Å (Fig. 3[link]). No other directional supra­molecular inter­actions are present in the crystal packing of the title compound.

[Figure 2]
Figure 2
Packing for the title complex; H atoms are omitted for clarity.
[Figure 3]
Figure 3
Capped stick representation of the title mol­ecule showing the ππ stacking inter­actions (red).

Synthesis and crystallization

Silver tri­fluoro­methane­sulfonate (0.377 g, 14.7 mmol) was added to an aceto­nitrile solution of zinc chloride (0.100 g, 7.34 mmol). The resulting solution was filtrated using a 0.45 mm PTFE syringe filter to remove silver chloride, and 4′-chloro-2,2′:6′,2′′-terpyridine (0.393 g, 14.7 mmol) was added to yield the title compound. Crystals suitable for X-ray diffraction were obtained by vapor diffusion of diethyl ether over the resulting aceto­nitrile solution at 277 K.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. The structure was refined as a two-component twin with a final BASF parameter of 0.4619 (17).

Table 2
Experimental details

Crystal data
Chemical formula [Zn(C15H10ClN3)2](CF3O3S)2
Mr 898.93
Crystal system, space group Monoclinic, P21/c
Temperature (K) 100
a, b, c (Å) 8.9259 (2), 17.0711 (4), 22.0466 (5)
β (°) 90.287 (2)
V3) 3359.31 (13)
Z 4
Radiation type Cu Kα
μ (mm−1) 4.46
Crystal size (mm) 0.22 × 0.07 × 0.04
 
Data collection
Diffractometer XtaLAB Synergy, Dualflex, HyPix
Absorption correction Gaussian (CrysAlis PRO; Rigaku OD, 2019[Rigaku OD (2019). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.])
Tmin, Tmax 0.995, 0.999
No. of measured, independent and observed [I > 2σ(I)] reflections 8675, 8675, 8049
Rint 0.065
(sin θ/λ)max−1) 0.600
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.069, 0.145, 1.15
No. of reflections 8675
No. of parameters 497
H-atom treatment H-atom parameters constrained
   
Δρmax, Δρmin (e Å−3) 0.93, −0.71
Computer programs: CrysAlis PRO (Rigaku OD, 2019[Rigaku OD (2019). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]), SHELXT (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL2018/3 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]) and OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]).

Structural data


Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2019); cell refinement: CrysAlis PRO (Rigaku OD, 2019); data reduction: CrysAlis PRO (Rigaku OD, 2019); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: Olex2 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 (Dolomanov et al., 2009).

Bis(4'-chloro-2,2':6',2''-terpyridine-κ3N,N',N'')zinc(II) bis(trifluoromethanesulfonate) top
Crystal data top
[Zn(C15H10ClN3)2](CF3O3S)2F(000) = 1808
Mr = 898.93Dx = 1.777 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54184 Å
a = 8.9259 (2) ÅCell parameters from 10902 reflections
b = 17.0711 (4) Åθ = 5.0–67.4°
c = 22.0466 (5) ŵ = 4.46 mm1
β = 90.287 (2)°T = 100 K
V = 3359.31 (13) Å3Needle, clear colourless
Z = 40.22 × 0.07 × 0.04 mm
Data collection top
XtaLAB Synergy, Dualflex, HyPix
diffractometer
8675 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source8049 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.065
Detector resolution: 10.0000 pixels mm-1θmax = 67.8°, θmin = 3.3°
ω scansh = 1010
Absorption correction: gaussian
(CrysAlisPro; Rigaku OD, 2019)
k = 2020
Tmin = 0.995, Tmax = 0.999l = 2626
8675 measured reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.069H-atom parameters constrained
wR(F2) = 0.145 w = 1/[σ2(Fo2) + (0.010P)2 + 25.P]
where P = (Fo2 + 2Fc2)/3
S = 1.15(Δ/σ)max < 0.001
8675 reflectionsΔρmax = 0.93 e Å3
497 parametersΔρmin = 0.71 e Å3
0 restraints
Special details top

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. Refined as a 2-component twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Zn10.73770 (11)0.49335 (5)0.28538 (3)0.01471 (19)
S11.0279 (2)0.23997 (10)0.39877 (7)0.0239 (4)
Cl20.7635 (3)0.50475 (11)0.01113 (6)0.0255 (4)
S20.5232 (3)0.25502 (11)0.60978 (8)0.0295 (4)
Cl10.7454 (3)0.50507 (12)0.58105 (6)0.0373 (5)
N40.7432 (7)0.4932 (3)0.1897 (2)0.0153 (10)
N10.7376 (8)0.4982 (3)0.3796 (2)0.0180 (12)
F10.9720 (6)0.1766 (3)0.50582 (18)0.0368 (11)
F30.7919 (6)0.1670 (3)0.4403 (2)0.0482 (14)
C180.7554 (10)0.4998 (4)0.0672 (2)0.0176 (12)
N30.6338 (6)0.3825 (3)0.3132 (2)0.0174 (12)
F60.5121 (6)0.1630 (3)0.51400 (19)0.0411 (12)
N50.5255 (7)0.5454 (3)0.2570 (2)0.0150 (11)
F40.4119 (7)0.1162 (3)0.5956 (2)0.0442 (13)
N60.9532 (7)0.4437 (3)0.2627 (2)0.0161 (11)
F20.8370 (6)0.2769 (3)0.4839 (2)0.0384 (11)
O60.4198 (7)0.2660 (3)0.6583 (2)0.0303 (13)
N20.8412 (7)0.6064 (3)0.3076 (2)0.0163 (11)
F50.2979 (7)0.2035 (4)0.5441 (3)0.0618 (18)
O10.9262 (7)0.2684 (3)0.3526 (2)0.0333 (13)
C120.5253 (9)0.3153 (4)0.3973 (3)0.0197 (14)
H120.5071010.3125680.4387780.024*
C50.6718 (8)0.4400 (4)0.4114 (3)0.0174 (13)
O21.1243 (7)0.2976 (4)0.4263 (2)0.0369 (14)
C200.8656 (8)0.4685 (4)0.1615 (3)0.0162 (13)
C281.2298 (8)0.3884 (4)0.2245 (3)0.0212 (14)
H281.3220730.3695200.2116540.025*
C291.1960 (7)0.3915 (4)0.2852 (3)0.0189 (14)
H291.2652850.3752020.3142580.023*
C240.2846 (8)0.6020 (4)0.2747 (3)0.0229 (15)
H240.2130800.6194380.3021290.027*
C160.6264 (8)0.5214 (4)0.1585 (3)0.0165 (13)
C170.6272 (8)0.5258 (4)0.0961 (3)0.0175 (13)
H170.5456380.5452770.0744630.021*
C10.7991 (8)0.5595 (4)0.4083 (3)0.0185 (14)
C60.8651 (8)0.6192 (4)0.3676 (3)0.0160 (13)
O31.0984 (9)0.1662 (3)0.3834 (3)0.0455 (17)
C220.3669 (8)0.5775 (4)0.1736 (3)0.0180 (14)
H220.3499750.5783900.1319820.022*
C150.5834 (8)0.3253 (4)0.2760 (3)0.0187 (14)
H150.6050540.3283220.2348020.022*
C260.9879 (8)0.4410 (3)0.2022 (3)0.0139 (13)
C90.9789 (8)0.7236 (4)0.2867 (3)0.0196 (13)
H91.0152820.7588180.2581900.023*
C210.5004 (8)0.5490 (4)0.1966 (3)0.0149 (13)
C230.2574 (8)0.6051 (4)0.2134 (3)0.0203 (13)
H230.1675470.6251300.1985810.024*
C30.7381 (11)0.5025 (5)0.5027 (3)0.0248 (16)
C110.6082 (8)0.3759 (4)0.3733 (3)0.0171 (14)
C190.8777 (8)0.4698 (4)0.0988 (3)0.0174 (13)
H190.9627400.4516170.0790140.021*
C40.6738 (9)0.4398 (4)0.4739 (3)0.0210 (15)
H40.6329680.3984900.4957910.025*
C20.8041 (9)0.5644 (4)0.4712 (3)0.0241 (16)
H20.8487640.6064710.4911010.029*
C301.0565 (8)0.4192 (4)0.3022 (3)0.0178 (14)
H301.0338840.4209370.3433560.021*
C100.8965 (8)0.6589 (4)0.2685 (3)0.0171 (13)
H100.8786630.6516260.2273010.021*
C81.0062 (8)0.7350 (4)0.3471 (3)0.0222 (15)
H81.0636140.7772590.3602150.027*
C140.4998 (8)0.2620 (4)0.2971 (3)0.0232 (15)
H140.4655690.2233320.2707480.028*
C130.4697 (8)0.2586 (4)0.3584 (3)0.0181 (14)
H130.4116360.2179430.3736120.022*
C250.4210 (8)0.5724 (4)0.2951 (3)0.0206 (14)
H250.4403340.5712810.3365360.025*
C70.9467 (8)0.6822 (4)0.3889 (3)0.0209 (15)
H70.9617690.6893240.4303300.025*
O50.6589 (7)0.2185 (5)0.6262 (3)0.059 (2)
O40.5307 (13)0.3215 (4)0.5698 (3)0.074 (3)
C271.1232 (8)0.4142 (4)0.1825 (3)0.0192 (14)
H271.1443980.4132310.1412030.023*
C310.9012 (9)0.2133 (5)0.4603 (3)0.0294 (17)
C320.4313 (9)0.1828 (5)0.5623 (3)0.0294 (17)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0177 (4)0.0154 (4)0.0110 (3)0.0014 (3)0.0032 (4)0.0000 (3)
S10.0294 (9)0.0212 (9)0.0211 (8)0.0002 (8)0.0055 (7)0.0027 (6)
Cl20.0317 (10)0.0332 (9)0.0115 (7)0.0024 (8)0.0014 (7)0.0009 (6)
S20.0413 (11)0.0276 (10)0.0195 (8)0.0150 (8)0.0009 (8)0.0006 (6)
Cl10.0641 (14)0.0379 (10)0.0099 (7)0.0228 (10)0.0019 (9)0.0015 (6)
N40.012 (3)0.017 (3)0.017 (2)0.000 (2)0.003 (2)0.0054 (19)
N10.028 (3)0.013 (2)0.013 (2)0.001 (2)0.006 (3)0.0007 (19)
F10.049 (3)0.036 (3)0.026 (2)0.000 (2)0.006 (2)0.0077 (17)
F30.056 (4)0.050 (3)0.039 (3)0.031 (3)0.014 (2)0.011 (2)
C180.023 (3)0.016 (3)0.013 (3)0.003 (3)0.002 (3)0.001 (2)
N30.014 (3)0.015 (3)0.023 (3)0.003 (2)0.006 (2)0.003 (2)
F60.054 (3)0.045 (3)0.025 (2)0.006 (3)0.011 (2)0.0151 (19)
N50.017 (3)0.012 (3)0.016 (2)0.001 (2)0.000 (2)0.0013 (18)
F40.064 (4)0.027 (3)0.043 (3)0.015 (2)0.007 (3)0.0049 (19)
N60.019 (3)0.015 (3)0.014 (2)0.001 (2)0.002 (2)0.0011 (19)
F20.037 (3)0.045 (3)0.034 (2)0.008 (2)0.002 (2)0.0034 (19)
O60.047 (4)0.025 (3)0.019 (2)0.000 (2)0.004 (2)0.0014 (19)
N20.020 (3)0.016 (3)0.012 (3)0.005 (2)0.000 (2)0.0016 (19)
F50.049 (4)0.076 (4)0.061 (3)0.022 (3)0.032 (3)0.030 (3)
O10.036 (3)0.034 (3)0.030 (3)0.000 (3)0.009 (2)0.008 (2)
C120.027 (4)0.016 (3)0.015 (3)0.000 (3)0.004 (3)0.003 (2)
C50.013 (3)0.018 (3)0.021 (3)0.002 (3)0.004 (3)0.003 (2)
O20.038 (3)0.040 (4)0.032 (3)0.019 (3)0.005 (3)0.001 (2)
C200.020 (4)0.009 (3)0.020 (3)0.000 (3)0.003 (3)0.002 (2)
C280.021 (4)0.019 (3)0.024 (3)0.002 (3)0.006 (3)0.002 (2)
C290.018 (3)0.015 (3)0.024 (3)0.003 (3)0.006 (3)0.002 (3)
C240.016 (3)0.020 (3)0.033 (4)0.002 (3)0.006 (3)0.000 (3)
C160.016 (3)0.015 (3)0.019 (3)0.004 (3)0.008 (3)0.001 (2)
C170.017 (3)0.017 (3)0.018 (3)0.001 (3)0.007 (3)0.000 (2)
C10.024 (4)0.016 (3)0.015 (3)0.003 (3)0.002 (3)0.001 (2)
C60.018 (3)0.017 (3)0.012 (3)0.003 (3)0.000 (2)0.000 (2)
O30.072 (5)0.028 (3)0.036 (3)0.022 (3)0.002 (3)0.010 (2)
C220.019 (4)0.015 (3)0.019 (3)0.002 (3)0.000 (3)0.000 (2)
C150.025 (4)0.015 (3)0.016 (3)0.005 (3)0.010 (3)0.004 (2)
C260.021 (3)0.008 (3)0.012 (3)0.002 (3)0.003 (3)0.003 (2)
C90.017 (3)0.016 (3)0.025 (3)0.004 (3)0.003 (3)0.006 (2)
C210.017 (3)0.012 (3)0.016 (3)0.001 (3)0.002 (3)0.000 (2)
C230.017 (3)0.021 (3)0.024 (3)0.004 (3)0.002 (3)0.002 (3)
C30.036 (4)0.027 (3)0.012 (3)0.005 (3)0.001 (3)0.001 (2)
C110.019 (4)0.014 (3)0.018 (3)0.001 (3)0.004 (3)0.002 (2)
C190.022 (4)0.017 (3)0.014 (3)0.000 (3)0.002 (3)0.001 (2)
C40.024 (4)0.022 (4)0.018 (3)0.006 (3)0.000 (3)0.003 (3)
C20.037 (5)0.020 (4)0.016 (3)0.001 (3)0.003 (3)0.002 (2)
C300.023 (4)0.017 (3)0.013 (3)0.001 (3)0.006 (3)0.002 (2)
C100.019 (4)0.015 (3)0.017 (3)0.005 (3)0.000 (3)0.003 (2)
C80.014 (3)0.017 (4)0.035 (4)0.000 (3)0.002 (3)0.002 (3)
C140.027 (4)0.016 (3)0.027 (4)0.003 (3)0.014 (3)0.006 (2)
C130.024 (3)0.012 (3)0.018 (3)0.000 (3)0.001 (3)0.004 (2)
C250.029 (4)0.016 (3)0.017 (3)0.001 (3)0.003 (3)0.001 (2)
C70.028 (4)0.018 (3)0.017 (3)0.001 (3)0.007 (3)0.003 (2)
O50.018 (3)0.110 (7)0.049 (4)0.002 (4)0.001 (3)0.025 (4)
O40.162 (9)0.027 (3)0.032 (3)0.033 (5)0.030 (4)0.004 (2)
C270.023 (4)0.016 (3)0.019 (3)0.000 (3)0.003 (3)0.001 (2)
C310.026 (4)0.032 (4)0.030 (4)0.007 (3)0.012 (3)0.001 (3)
C320.029 (4)0.032 (4)0.027 (4)0.002 (3)0.002 (3)0.010 (3)
Geometric parameters (Å, º) top
Zn1—N42.109 (5)C20—C261.486 (9)
Zn1—N12.079 (5)C20—C191.387 (9)
Zn1—N32.196 (6)C28—H280.9300
Zn1—N52.181 (6)C28—C291.375 (10)
Zn1—N62.163 (6)C28—C271.396 (9)
Zn1—N22.194 (6)C29—H290.9300
S1—O11.445 (6)C29—C301.386 (10)
S1—O21.439 (6)C24—H240.9300
S1—O31.449 (6)C24—C231.373 (10)
S1—C311.827 (8)C24—C251.391 (10)
Cl2—C181.730 (5)C16—C171.378 (9)
S2—O61.428 (6)C16—C211.483 (9)
S2—O51.408 (8)C17—H170.9300
S2—O41.439 (6)C1—C61.482 (9)
S2—C321.810 (8)C1—C21.389 (9)
Cl1—C31.728 (6)C6—C71.380 (10)
N4—C201.329 (9)C22—H220.9300
N4—C161.336 (9)C22—C211.381 (10)
N1—C51.353 (9)C22—C231.398 (9)
N1—C11.339 (9)C15—H150.9300
F1—C311.340 (9)C15—C141.395 (10)
F3—C311.328 (9)C26—C271.365 (10)
C18—C171.386 (10)C9—H90.9300
C18—C191.390 (10)C9—C101.385 (10)
N3—C151.351 (8)C9—C81.367 (10)
N3—C111.351 (9)C23—H230.9300
F6—C321.333 (9)C3—C41.369 (11)
N5—C211.352 (8)C3—C21.398 (11)
N5—C251.339 (9)C19—H190.9300
F4—C321.365 (10)C4—H40.9300
N6—C261.372 (8)C2—H20.9300
N6—C301.333 (9)C30—H300.9300
F2—C311.335 (9)C10—H100.9300
N2—C61.355 (8)C8—H80.9300
N2—C101.340 (8)C8—C71.395 (10)
F5—C321.303 (10)C14—H140.9300
C12—H120.9300C14—C131.380 (10)
C12—C111.380 (10)C13—H130.9300
C12—C131.384 (10)C25—H250.9300
C5—C111.490 (9)C7—H70.9300
C5—C41.378 (9)C27—H270.9300
N4—Zn1—N3106.9 (2)C2—C1—C6123.5 (6)
N4—Zn1—N574.8 (2)N2—C6—C1114.7 (6)
N4—Zn1—N675.1 (2)N2—C6—C7122.6 (6)
N4—Zn1—N2102.3 (2)C7—C6—C1122.7 (6)
N1—Zn1—N4177.4 (2)C21—C22—H22120.2
N1—Zn1—N375.7 (2)C21—C22—C23119.6 (6)
N1—Zn1—N5105.4 (2)C23—C22—H22120.2
N1—Zn1—N6104.5 (2)N3—C15—H15118.9
N1—Zn1—N275.1 (2)N3—C15—C14122.3 (6)
N5—Zn1—N393.6 (2)C14—C15—H15118.9
N5—Zn1—N294.0 (2)N6—C26—C20114.1 (6)
N6—Zn1—N395.9 (2)C27—C26—N6121.7 (6)
N6—Zn1—N5149.97 (18)C27—C26—C20124.2 (5)
N6—Zn1—N291.3 (2)C10—C9—H9120.4
N2—Zn1—N3150.86 (18)C8—C9—H9120.4
O1—S1—O3113.6 (4)C8—C9—C10119.2 (6)
O1—S1—C31102.6 (4)N5—C21—C16115.0 (6)
O2—S1—O1116.1 (4)N5—C21—C22121.0 (6)
O2—S1—O3115.6 (4)C22—C21—C16124.0 (6)
O2—S1—C31103.2 (3)C24—C23—C22119.0 (7)
O3—S1—C31103.2 (4)C24—C23—H23120.5
O6—S2—O4112.7 (4)C22—C23—H23120.5
O6—S2—C32103.3 (4)C4—C3—Cl1119.8 (6)
O5—S2—O6115.1 (4)C4—C3—C2122.5 (6)
O5—S2—O4117.6 (6)C2—C3—Cl1117.6 (6)
O5—S2—C32103.5 (4)N3—C11—C12122.2 (6)
O4—S2—C32101.9 (4)N3—C11—C5115.3 (6)
C20—N4—Zn1119.5 (4)C12—C11—C5122.5 (6)
C20—N4—C16120.9 (5)C18—C19—H19121.9
C16—N4—Zn1119.5 (5)C20—C19—C18116.1 (6)
C5—N1—Zn1119.4 (4)C20—C19—H19121.9
C1—N1—Zn1120.1 (4)C5—C4—H4121.1
C1—N1—C5120.5 (5)C3—C4—C5117.7 (7)
C17—C18—Cl2118.8 (6)C3—C4—H4121.1
C17—C18—C19122.4 (5)C1—C2—C3116.1 (7)
C19—C18—Cl2118.8 (6)C1—C2—H2122.0
C15—N3—Zn1126.4 (5)C3—C2—H2122.0
C15—N3—C11118.6 (6)N6—C30—C29123.3 (6)
C11—N3—Zn1114.8 (4)N6—C30—H30118.3
C21—N5—Zn1116.1 (5)C29—C30—H30118.3
C25—N5—Zn1124.6 (4)N2—C10—C9122.9 (6)
C25—N5—C21119.3 (6)N2—C10—H10118.5
C26—N6—Zn1116.3 (4)C9—C10—H10118.5
C30—N6—Zn1125.8 (4)C9—C8—H8120.5
C30—N6—C26117.9 (6)C9—C8—C7119.0 (7)
C6—N2—Zn1115.1 (4)C7—C8—H8120.5
C10—N2—Zn1126.9 (4)C15—C14—H14121.1
C10—N2—C6117.6 (6)C13—C14—C15117.8 (6)
C11—C12—H12120.7C13—C14—H14121.1
C11—C12—C13118.5 (6)C12—C13—H13119.8
C13—C12—H12120.7C14—C13—C12120.5 (7)
N1—C5—C11114.3 (6)C14—C13—H13119.8
N1—C5—C4121.1 (6)N5—C25—C24122.3 (6)
C4—C5—C11124.4 (6)N5—C25—H25118.8
N4—C20—C26114.8 (5)C24—C25—H25118.8
N4—C20—C19122.1 (6)C6—C7—C8118.7 (6)
C19—C20—C26123.1 (6)C6—C7—H7120.7
C29—C28—H28120.6C8—C7—H7120.7
C29—C28—C27118.9 (7)C28—C27—H27120.2
C27—C28—H28120.6C26—C27—C28119.7 (6)
C28—C29—H29120.7C26—C27—H27120.2
C28—C29—C30118.6 (6)F1—C31—S1112.4 (6)
C30—C29—H29120.7F3—C31—S1111.0 (5)
C23—C24—H24120.6F3—C31—F1108.2 (6)
C23—C24—C25118.8 (7)F3—C31—F2107.3 (7)
C25—C24—H24120.6F2—C31—S1110.9 (5)
N4—C16—C17121.8 (7)F2—C31—F1106.8 (6)
N4—C16—C21114.5 (5)F6—C32—S2112.9 (6)
C17—C16—C21123.8 (6)F6—C32—F4106.8 (6)
C18—C17—H17121.6F4—C32—S2108.3 (5)
C16—C17—C18116.8 (6)F5—C32—S2113.9 (6)
C16—C17—H17121.6F5—C32—F6108.7 (6)
N1—C1—C6114.5 (5)F5—C32—F4105.8 (7)
N1—C1—C2122.0 (6)
Zn1—N4—C20—C261.4 (7)C16—N4—C20—C26178.3 (5)
Zn1—N4—C20—C19177.6 (5)C16—N4—C20—C190.8 (10)
Zn1—N4—C16—C17177.1 (5)C17—C18—C19—C201.1 (11)
Zn1—N4—C16—C211.3 (8)C17—C16—C21—N5175.0 (6)
Zn1—N1—C5—C111.6 (8)C17—C16—C21—C224.1 (11)
Zn1—N1—C5—C4177.8 (6)C1—N1—C5—C11179.9 (6)
Zn1—N1—C1—C60.8 (9)C1—N1—C5—C43.9 (11)
Zn1—N1—C1—C2178.7 (6)C1—C6—C7—C8179.2 (7)
Zn1—N3—C15—C14170.6 (5)C6—N2—C10—C91.7 (10)
Zn1—N3—C11—C12170.7 (5)C6—C1—C2—C3179.2 (7)
Zn1—N3—C11—C57.4 (8)O3—S1—C31—F154.5 (6)
Zn1—N5—C21—C163.7 (7)O3—S1—C31—F366.9 (7)
Zn1—N5—C21—C22177.1 (5)O3—S1—C31—F2174.0 (5)
Zn1—N5—C25—C24177.2 (5)C15—N3—C11—C123.7 (10)
Zn1—N6—C26—C203.7 (7)C15—N3—C11—C5178.1 (6)
Zn1—N6—C26—C27177.0 (5)C15—C14—C13—C122.0 (11)
Zn1—N6—C30—C29176.6 (5)C26—N6—C30—C290.1 (10)
Zn1—N2—C6—C17.7 (7)C26—C20—C19—C18177.8 (6)
Zn1—N2—C6—C7171.2 (5)C9—C8—C7—C61.5 (11)
Zn1—N2—C10—C9170.5 (5)C21—N5—C25—C242.1 (10)
Cl2—C18—C17—C16179.4 (5)C21—C16—C17—C18178.0 (6)
Cl2—C18—C19—C20178.9 (5)C21—C22—C23—C240.9 (10)
Cl1—C3—C4—C5179.5 (6)C23—C24—C25—N51.3 (10)
Cl1—C3—C2—C1178.6 (6)C23—C22—C21—N51.7 (10)
N4—C20—C26—N61.6 (8)C23—C22—C21—C16177.4 (6)
N4—C20—C26—C27179.1 (6)C11—N3—C15—C143.2 (10)
N4—C20—C19—C181.1 (10)C11—C12—C13—C141.4 (11)
N4—C16—C17—C180.2 (10)C11—C5—C4—C3179.1 (7)
N4—C16—C21—N53.3 (8)C19—C18—C17—C160.6 (11)
N4—C16—C21—C22177.5 (6)C19—C20—C26—N6179.4 (6)
N1—C5—C11—N34.1 (9)C19—C20—C26—C270.1 (10)
N1—C5—C11—C12174.1 (7)C4—C5—C11—N3172.0 (7)
N1—C5—C4—C33.3 (12)C4—C5—C11—C129.9 (11)
N1—C1—C6—N25.8 (9)C4—C3—C2—C10.9 (13)
N1—C1—C6—C7173.1 (7)C2—C1—C6—N2176.4 (7)
N1—C1—C2—C31.4 (12)C2—C1—C6—C74.8 (11)
N3—C15—C14—C130.3 (10)C2—C3—C4—C51.8 (13)
N6—C26—C27—C280.3 (10)C30—N6—C26—C20179.4 (5)
O6—S2—C32—F6179.0 (6)C30—N6—C26—C270.1 (9)
O6—S2—C32—F460.9 (6)C10—N2—C6—C1179.1 (6)
O6—S2—C32—F556.5 (7)C10—N2—C6—C72.0 (10)
N2—C6—C7—C80.4 (11)C10—C9—C8—C71.7 (10)
O1—S1—C31—F1172.7 (5)C8—C9—C10—N20.1 (10)
O1—S1—C31—F351.3 (7)C13—C12—C11—N31.5 (11)
O1—S1—C31—F267.8 (5)C13—C12—C11—C5179.5 (7)
C5—N1—C1—C6179.1 (6)C25—N5—C21—C16176.9 (6)
C5—N1—C1—C22.9 (11)C25—N5—C21—C222.3 (9)
O2—S1—C31—F166.3 (6)C25—C24—C23—C220.7 (10)
O2—S1—C31—F3172.3 (6)O5—S2—C32—F658.6 (7)
O2—S1—C31—F253.2 (6)O5—S2—C32—F459.5 (6)
C20—N4—C16—C170.3 (10)O5—S2—C32—F5176.9 (7)
C20—N4—C16—C21178.1 (5)O4—S2—C32—F663.9 (8)
C20—C26—C27—C28178.9 (6)O4—S2—C32—F4178.0 (6)
C28—C29—C30—N60.3 (10)O4—S2—C32—F560.6 (8)
C29—C28—C27—C260.7 (10)C27—C28—C29—C300.7 (10)
 

Acknowledgements

We are thankful for the support of the Department of Chemistry and Biochemistry at the University of the Incarnate Word and the X-ray Diffraction Laboratory at the University of Texas at San Antonio.

Funding information

Funding for this research was provided by: National Science Foundation (award No. 1920059); Welch Foundation (award No. BN0032).

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