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ISSN: 2056-9890

Crystal structure of {(R)-N2-[(benzo[h]quinolin-2-yl)meth­yl]-N2′-[(benzo[h]quinolin-2-yl)methyl­­idene]-1,1′-bi­naphthyl-2,2′-di­amine-κ4N,N′,N′′,N′′′}(tri­fluoro­methane­sulfonato-κO)zinc(II)} tri­fluoro­methane­sulfonate di­chloro­methane 1.5-solvate

aDepartment of Chemistry, Creighton University, Omaha, NE 68102, USA, bDepartment of Chemistry, University of Wisconsin, Madison, WI 53558, USA, and cDepartment of Chemistry, Kansas State University, Manhattan, KS 66506, USA
*Correspondence e-mail: kayodeoshin@creighton.edu

Edited by W. Imhof, University Koblenz-Landau, Germany (Received 11 April 2017; accepted 30 May 2017; online 2 June 2017)

The zinc(II) atom in the title compound, [Zn(C48H31N4)(CF3SO3)](CF3SO3)·1.5CH2Cl2, adopts a distorted five-coordinate square-pyramidal geometry. It is coordinated by one tri­fluoro­methane­sulfonate ligand and four N atoms of the N2-[(benzo[h]quinolin-2-yl)meth­yl]-N2′-[(benzo[h]quinolin-2-yl)methyl­idene]-1,1′-binaphthyl-2,2′-di­amine ligand. The complex is present as a single-stranded P-helimer monohelical structure incorporating ππ and/or σπ inter­actions. One of the imine bonds present in the original ligand framework is reduced, leading to variations in bond lengths and torsion angles for each side of the ligand motif. The imine-bond reduction also affects the bond lengths involving the metal atom with the N-donor atoms located on the imine bond. There are two mol­ecules of the complex in the asymmetric unit. One of the mol­ecules exhibits positional disorder within the coordinating tri­fluoro­methane­sulfonate ion making the mol­ecules symmetric­ally non-equivalent.

1. Chemical context

Stereochemistry plays a very important role in the chemical inter­actions that dominate several fields of chemistry (North, 1998[North, M. (1998). In Principles and Applications of Stereochemistry. Cheltenham: Stanley Thornes Publishers.]). For example, in pharmacology enanti­omers of chiral drugs exhibit marked differences in toxicology, metabolism, immune response, and pharmacokinetics (Nguyen et al., 2006[Nguyen, L. A., He, H. & Pham-Huy, C. (2006). Int. J. Biomed. Sci. 2, 85-100.]). As a result, there is increased demand to design practical methods to synthesize monohelical chiral compounds for use as catalysts (Aspinall, 2002[Aspinall, H. C. (2002). Chem. Rev. 102, 1807-1850.]). Many factors contribute to the efficiency of a catalyst such as the type of metal employed, the presence of electron-donating or withdrawing functional groups, the number of chiral centers present, and regeneration capabilities (Amendola et al., 1999[Amendola, V., Fabbrizzi, L. M., Linati, L., Mangano, C., Pallavicini, P., Pedrazzini, V. & Zema, M. (1999). Chem. Eur. J. 5, 3679-3688.]). In addition, substrate accessibility to the metal atom plays an important role in catalytic reactions (French, 2007[French, S. A. (2007). Plat. Met. Rev. 51, 54-62.]). Using bulky ligands in catalyst design may result in steric hindrance of the active site, a reduction in enanti­omeric excess values, and lower yields (French, 2007[French, S. A. (2007). Plat. Met. Rev. 51, 54-62.]). Studies of catalytic mechanisms show that substrates generally approach the active site through the least hindered quadrant during a reaction (French, 2007[French, S. A. (2007). Plat. Met. Rev. 51, 54-62.]). Designing catalysts with increased flexibility which undergo slight conformation changes as substrates approach should result in increased efficiency. This concept can be observed in nature where some enzymes can adopt flexible active sites, unlike the typical `lock and key' model commonly used, allowing them to shape those active sites to accommodate bulkier substrates leading to improving efficiency (Tsou, 1993[Tsou, C. (1993). Science, 262, 380-381.]). Given the significance and application of flexible single-stranded monohelical complexes in asymmetric catalysis, we report on the synthesis and crystal structure of the solvated title compound, [Zn(C48H32N4)(CF3O3S)](CF3O3S)·1.5CH2Cl2 (1).

[Scheme 1]

2. Structural commentary

X-ray analysis revealed a monohelical structure (Fig. 1[link]) with ππ and/or σπ inter­actions between the locked side-arms of complex (1). The ZnII cation is coordinated by four N-donor atoms from the N2-[(benzo[h]quinolin-2-yl)meth­yl]-N2′-[(benzo[h]quinolin-2-yl)methyl­idene]-1,1′-binaphthyl-2,2′-di­amine (BQMB) ligand and one triflate anion in a distorted square-pyramidal geometry (τ5 = 0.49; Addison et al., 1984[Addison, A. W., Rao, T. N., Reedijk, J., van Rijn, J. & Verschoor, G. C. (1984). J. Chem. Soc. Dalton Trans. pp. 1349-1356.]). We observed the reduction of one imine double bond as the C—N bond length of the unreduced imine is 1.281 (6) Å while the C—N bond length of the reduced imine is 1.433 (6) Å. We also observed the effect of the reduction in the torsion angle as the amine side (C33—C34—N3—C36) is −22.6 (5)° while the torsion angle for the imine side (C16—C15—N2—C13) is 33.0 (7)°. The reduction of the imine bond also affects the bond lengths of the zinc metal center with the N-donor atoms on the imine bond. As a result of the flexibility of the amine side, we observe a longer bond length for the Zn—N bond [2.253 (4) Å] compared to a shorter Zn—N bond length with the more rigid imine nitro­gen atom [2.056 (4) Å]. The bi­naphthalene backbone displays a twist to a degree of 76.54 (6)°.

[Figure 1]
Figure 1
The mol­ecular structure for one of the mol­ecules of complex (1). Atomic displacement ellipsoids are depicted at the 50% probability level and H atoms are shown as spheres of arbitrary radius. All non-imine/amino H atoms and solvent mol­ecules have been omitted for clarity.

3. Supra­molecular features

The mol­ecules of the crystal structure are related only by a twofold screw axis running along the b-axis direction (Fig. 2[link]). The resulting space group P21 is chiral. The Flack x and the Hooft y parameters were determined to be −0.008 (4) and 0.003 (4), respectively, indicating that the absolute structure was unequivocally established. Anomalous dispersion was used to determine the absolute structure. There are two mol­ecules of complex (1) in the asymmetric unit. As seen in Fig. 3[link], the difference in the two mol­ecules arises due to the orientation of the coordinating triflate. In addition, one of the mol­ecules exhibits positional disorder within the coordinating triflate ion. As a result, the two mol­ecules are not symmetry equivalent. Minimal intra­molecular inter­actions are observed between the mol­ecules of (1). The two mol­ecules of (1) in the asymmetric unit propagate along the b-axis direction via the twofold screw axis. The counter-ions and the solvent mol­ecules fill the void spaces between symmetry-related asymmetric units.

[Figure 2]
Figure 2
Packing diagram for complex (1), viewed along the a-axis direction. Minimal inter­actions are observed between the packed mol­ecules.
[Figure 3]
Figure 3
Overlay of the two mol­ecules of complex (1) in the asymmetric unit. Atomic displacement ellipsoids are depicted at the 50% probability and H atoms shown as spheres of arbitrary radius. All hydrogen atoms, counter-ions, solvent mol­ecules, and minor-disorder components have been omitted for clarity.

4. Database survey

The survey of Cambridge Structural Database (Groom et al., 2016[Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171-179.]) revealed five instances of five-coordinate Zn complexes bonding through four amine groups and one triflate. Of the five complexes, two assume a trigonal–bipyramidal geometry (with τ5 values of 0.86 and 0.93), two structures have a square-pyramidal geometry (τ5 values of 0.02 and 0.11), and the last structure assumes a distorted square-pyramidal geometry as evidenced by the τ5 value of 0.48. The Zn­—O bond length for (1) falls on the shorter end of the distance spectrum. Meanwhile the Zn—N distances for three of the contacts agree well with those in the previously reported structures. The fourth contact at a distance of 2.253 (4) Å falls above the average Zn—N distance by 0.176 Å, presumably due to the greater flexibility within the ligand framework resulting from the imine reduction.

5. Synthesis and crystallization

The synthetic scheme for (1) is given in Fig. 4[link].

[Figure 4]
Figure 4
Synthetic scheme for complex (1)

Synthesis of (R)-N,N′-bis­[(2-benzo[h]quinolin­yl)methylene][1,1′-bi­naphthalene]-2,2′-di­amine (BQMB) ligand: the BQMB ligand was synthesized following established literature procedures (Prema et al., 2012[Prema, D., Oshin, K., Desper, J. & Levy, C. J. (2012). Dalton Trans. 41, 4998-5009.]). In a 100 ml round-bottom flask, (R)-[1,1′-binapthalene]-2,2′-di­amine (0.52 g, 1.8 mmol) and 2-formyl­benzo­quinoline (0.75 g, 3.6 mmol) were refluxed in ethanol (25 ml) for 2 h. A yellow precipitate was obtained, which was filtered and washed twice with 10 ml aliquots of ethanol. The resulting yellow mixture was dried under vacuum for 30 minutes to afford BQMB as a yellow solid (1.11 g, 92% yield). 1H NMR (CD2Cl2, 800 MHz): 7.32 (t, 2 H, J = 8.00 Hz, CH), 7.35 (d, 2 H, J = 8.06 Hz, CH), 7.40 (t, 2 H, J = 7.05 Hz, CH), 7.46 (t, 2 H, J = 7.00 Hz, CH), 7.55 (t, 2 H, J = 7.00 Hz, CH), 7.58 (d, 2 H, J = 8.56 Hz, CH), 7.63 (d, 2 H, J = 9.06 Hz, CH), 7.72 (d, 2 H, J = 8.56 Hz, CH), 7.77 (d, 2 H, J = 7.55 Hz, CH), 7.81 (d, 2 H, J = 8.06 Hz, CH), 8.01 (d, 2 H, J = 8.06 Hz, CH), 8.07 (d, 2 H, J = 8.06 Hz, CH), 8.10 (d, 2 H, J = 8.56 Hz, CH), 8.70 (s, 2 H, CH), 8.80 (d, 2 H, J = 8.06 Hz, CH). 13C NMR (CD2Cl2, 200 MHz): δ 119.16, 119.33, 124.39, 125.54, 125.76, 127.05, 127.35, 127.46, 127.62, 128.19, 128.34, 128.56, 128.67, 129.23, 130.04, 131.68, 132.76, 134.01, 134.04, 136.67, 146.35, 148.72, 153.89, 162.82. Elemental analysis for (C48H30N4): calculated C 86.98, H 4.56, N 8.45; found C 86.97, H 4.85, N 8.45.

Synthesis of {(R)-N2-[(benzo[h]quinolin-2-yl)meth­yl]-N2′-[(benzo[h]quinolin-2-yl)methyl­idene]-1,1′-binaphthyl-2,2′-di­amine-κ4N,N,N′′,N′′′}(trifluoromethane­sulfonato-κO)zinc(II)} trifluoromethane­sulfonate di­chloro­methane 1.5-solvate: the BQMB ligand (0.100 g, 0.151 mmol) was dissolved in a mixture of 15 ml ethanol and 10 ml tetra­hydro­furan in a 100 ml round-bottom flask. Sodium borohydride (0.010 g, 0.23 mmol) and zinc(II) trifluoromethanesulfonate (0.055 g, 0.15 mmol) were added to the flask to give an orange-colored solution. The reaction was allowed to reflux for 15 h and then cooled, producing a reddish-orange-colored precipitate which was filtered and washed twice with a cold solvent mixture. The precipitate was dried under vacuum for 30 minutes to yield a reddish-orange-colored solid (0.112 g, 72%). Reddish-orange-colored single crystals suitable for X-ray analysis were obtained by slow solvent diffusion of hexane into a concentrated complex solution in di­chloro­methane.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1[link]. Direct methods were used for identify positions of most of the non-hydrogen atoms and a procedure of alternating rounds between least-squares cycles and difference-Fourier maps, located the missing non-hydrogen atoms. All hydrogen atoms, except for the amine hydrogens bonded to N3 and N3A were refined at idealized positions and allowed to ride on neighboring atoms with relative isotropic displacement parameters. The amine hydrogen atoms were refined as riding freely. The asymmetric unit contains two mol­ecules of (1), two triflate counter-ions, and three mol­ecules of di­chloro­methane solvent. One of the mol­ecules of (1) exhibited positional disorder within the coordinating triflate ion. The positional disorder was modeled over two positions with the major component contributing 88.1 (4)%. Due to the low occupancy of the minor component, idealized geometry was used to stabilize the refinement and the component was refined isotropically. Additional disorder was observed in one of the solvent mol­ecules of di­chloro­methane. Two positions were used to model the positional disorder and the major component refined to occupancy of 50 (4)%. The bond lengths C54A—Cl5A and C54A—Cl6A were restrained to be similar.

Table 1
Experimental details

Crystal data
Chemical formula [Zn(C48H32N4)(CF3O3S)](CF3O3S)·1.5CH2Cl2
Mr 1155.70
Crystal system, space group Monoclinic, P21
Temperature (K) 120
a, b, c (Å) 11.837 (4), 23.126 (7), 17.836 (5)
β (°) 94.165 (10)
V3) 4870 (3)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.83
Crystal size (mm) 0.24 × 0.2 × 0.16
 
Data collection
Diffractometer Bruker APEXII CCD
Absorption correction Multi-scan (SADABS; Bruker, 2016[Bruker (2016). APEX2, SAINT, and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.691, 0.744
No. of measured, independent and observed [I > 2σ(I)] reflections 100143, 19958, 17492
Rint 0.073
(sin θ/λ)max−1) 0.627
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.092, 1.03
No. of reflections 19958
No. of parameters 1373
No. of restraints 2
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 0.61, −0.46
Absolute structure Flack x determined using 7334 quotients [(I+)−(I)]/[(I+)+(I)] (Parsons et al., 2013[Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249-259.])
Absolute structure parameter −0.008 (4)
Computer programs: APEX2 and SAINT (Bruker, 2016[Bruker (2016). APEX2, SAINT, and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXT (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL (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.]).

Supporting information


Computing details top

Data collection: APEX2 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

{(R)-N2-[(Benzo[h]quinolin-2-yl)methyl]-N2'-[(benzo[h]quinolin-2-yl)methylidene]-1,1'-binaphthyl-2,2'-diamine-κ4N,N',N'',N'''}(trifluoromethanesulfonato-κO)zinc(II)} trifluoromethanesulfonate dichloromethane 1.5-solvate top
Crystal data top
[Zn(C48H32N4)(CF3O3S)](CF3O3S)·1.5CH2Cl2F(000) = 2348
Mr = 1155.70Dx = 1.576 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 11.837 (4) ÅCell parameters from 9757 reflections
b = 23.126 (7) Åθ = 2.2–25.8°
c = 17.836 (5) ŵ = 0.83 mm1
β = 94.165 (10)°T = 120 K
V = 4870 (3) Å3Prism, orange
Z = 40.24 × 0.2 × 0.16 mm
Data collection top
Bruker APEXII CCD
diffractometer
19958 independent reflections
Radiation source: fine-focus sealed tube17492 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.073
φ and ω scansθmax = 26.5°, θmin = 1.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
h = 1414
Tmin = 0.691, Tmax = 0.744k = 2828
100143 measured reflectionsl = 2222
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.039 w = 1/[σ2(Fo2) + (0.0435P)2 + 1.1811P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.092(Δ/σ)max < 0.001
S = 1.03Δρmax = 0.61 e Å3
19958 reflectionsΔρmin = 0.46 e Å3
1373 parametersAbsolute structure: Flack x determined using 7334 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
2 restraintsAbsolute structure parameter: 0.008 (4)
Primary atom site location: dual
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Zn10.43047 (4)0.36244 (2)1.02612 (3)0.01811 (12)
S10.64940 (9)0.34588 (5)1.13414 (6)0.0201 (2)
F10.7184 (3)0.23936 (13)1.14727 (19)0.0488 (9)
F20.7876 (2)0.29519 (14)1.23511 (17)0.0387 (7)
F30.6145 (3)0.26621 (14)1.23408 (19)0.0430 (8)
O10.5515 (3)0.31988 (14)1.09083 (19)0.0281 (8)
O20.7407 (3)0.35829 (17)1.08853 (19)0.0328 (8)
O30.6167 (3)0.38875 (14)1.18579 (18)0.0302 (8)
N10.3008 (3)0.37869 (16)1.1026 (2)0.0191 (8)
N20.4550 (3)0.44962 (16)1.04307 (19)0.0185 (7)
N30.5612 (3)0.35750 (17)0.9406 (2)0.0220 (8)
H30.620 (4)0.370 (2)0.962 (3)0.026*
N40.3657 (3)0.30238 (16)0.9493 (2)0.0210 (8)
C10.2150 (4)0.3443 (2)1.1236 (2)0.0197 (9)
C20.2297 (4)0.28197 (19)1.1269 (2)0.0188 (9)
C30.3357 (4)0.2555 (2)1.1252 (3)0.0245 (10)
H3B0.4014410.2788441.1230020.029*
C40.3467 (4)0.1964 (2)1.1265 (3)0.0299 (11)
H40.4193110.1792511.1243310.036*
C50.2510 (4)0.1613 (2)1.1312 (3)0.0307 (11)
H50.2579360.1203391.1303600.037*
C60.1469 (4)0.1866 (2)1.1369 (3)0.0283 (11)
H60.0825950.1626601.1418130.034*
C70.1334 (4)0.2468 (2)1.1357 (2)0.0231 (10)
C80.0258 (4)0.2736 (2)1.1455 (3)0.0275 (11)
H80.0394180.2499241.1479350.033*
C90.0149 (4)0.3310 (2)1.1513 (3)0.0279 (11)
H90.0559990.3471231.1618020.033*
C100.1100 (4)0.3686 (2)1.1416 (2)0.0232 (10)
C110.1017 (4)0.4291 (2)1.1479 (3)0.0294 (11)
H110.0331690.4462611.1614580.035*
C120.1930 (4)0.4635 (2)1.1343 (3)0.0250 (10)
H120.1911020.5040751.1422140.030*
C130.2883 (4)0.4367 (2)1.1087 (2)0.0206 (10)
C140.3840 (4)0.4718 (2)1.0856 (3)0.0213 (10)
H140.3927860.5106791.1023080.026*
C150.5583 (4)0.47927 (18)1.0293 (3)0.0185 (9)
C160.6218 (4)0.50475 (19)1.0905 (3)0.0223 (10)
H160.5913090.5067031.1382590.027*
C170.7265 (4)0.52656 (19)1.0813 (3)0.0231 (10)
H170.7693020.5429361.1231300.028*
C180.7727 (4)0.52526 (19)1.0105 (3)0.0216 (10)
C190.8835 (4)0.5465 (2)1.0002 (3)0.0257 (10)
H190.9283590.5618841.0418060.031*
C200.9259 (4)0.5450 (2)0.9310 (3)0.0291 (11)
H200.9989160.5605440.9246490.035*
C210.8624 (4)0.5207 (2)0.8691 (3)0.0282 (11)
H210.8934430.5190830.8214520.034*
C220.7555 (4)0.4994 (2)0.8773 (3)0.0245 (10)
H220.7132790.4832530.8350520.029*
C230.7072 (4)0.50106 (19)0.9479 (3)0.0218 (10)
C240.5969 (4)0.47783 (18)0.9588 (2)0.0184 (9)
C250.5274 (3)0.4541 (2)0.8923 (2)0.0203 (9)
C260.4747 (3)0.4929 (2)0.8380 (2)0.0202 (9)
C270.4758 (4)0.5536 (2)0.8479 (3)0.0243 (10)
H270.5129910.5698230.8919410.029*
C280.4236 (4)0.5895 (2)0.7944 (3)0.0290 (11)
H280.4229960.6301070.8026960.035*
C290.3715 (4)0.5667 (2)0.7278 (3)0.0326 (12)
H290.3392280.5919000.6900460.039*
C300.3669 (4)0.5083 (2)0.7171 (3)0.0288 (11)
H300.3294840.4930490.6724720.035*
C310.4175 (4)0.4701 (2)0.7722 (3)0.0257 (11)
C320.4100 (4)0.4093 (2)0.7635 (3)0.0278 (11)
H320.3713490.3936180.7195590.033*
C330.4575 (4)0.3728 (2)0.8172 (3)0.0290 (11)
H330.4499150.3321990.8108900.035*
C340.5173 (4)0.3951 (2)0.8816 (2)0.0219 (10)
C350.5659 (4)0.2948 (2)0.9268 (3)0.0252 (10)
H35C0.6194320.2765690.9649820.030*
H35D0.5938980.2876680.8766770.030*
C360.4498 (4)0.2679 (2)0.9304 (3)0.0230 (10)
C370.4318 (4)0.2093 (2)0.9137 (3)0.0280 (11)
H370.4924640.1854720.9002410.034*
C380.3253 (4)0.1870 (2)0.9173 (3)0.0285 (11)
H380.3130620.1467230.9098210.034*
C390.2335 (4)0.2231 (2)0.9319 (2)0.0251 (10)
C400.1194 (4)0.2022 (2)0.9355 (3)0.0313 (12)
H400.1039690.1621150.9289790.038*
C410.0348 (4)0.2387 (2)0.9481 (3)0.0305 (11)
H410.0389150.2237870.9535970.037*
C420.0537 (4)0.3001 (2)0.9532 (3)0.0271 (11)
C430.0380 (4)0.3386 (2)0.9599 (3)0.0332 (12)
H430.1118390.3238510.9652190.040*
C440.0203 (4)0.3968 (2)0.9586 (3)0.0335 (12)
H440.0821850.4222750.9637800.040*
C450.0879 (4)0.4197 (2)0.9497 (3)0.0291 (11)
H450.0985820.4603810.9480530.035*
C460.1785 (4)0.3830 (2)0.9434 (3)0.0236 (10)
H460.2511540.3984200.9357250.028*
C470.1634 (4)0.3225 (2)0.9484 (2)0.0222 (10)
C480.2560 (4)0.2821 (2)0.9441 (2)0.0206 (9)
C490.6944 (4)0.2830 (2)1.1909 (3)0.0289 (11)
Zn1A0.02835 (4)0.44769 (2)0.46179 (3)0.02053 (12)
S1A0.21493 (10)0.42631 (6)0.37632 (7)0.0202 (4)0.881 (4)
S1B0.1362 (10)0.4504 (6)0.3140 (7)0.051 (4)*0.119 (4)
O2B0.1035 (17)0.5099 (7)0.3037 (15)0.06 (3)*0.119 (4)
O3B0.1420 (17)0.4151 (11)0.2470 (10)0.07 (2)*0.119 (4)
O1B0.0874 (14)0.4228 (11)0.3815 (11)0.033 (16)*0.119 (4)
C49B0.2872 (10)0.4572 (8)0.3335 (10)0.025 (9)*0.119 (4)
F3B0.3344 (14)0.4057 (10)0.3449 (14)0.052 (9)*0.119 (4)
F1B0.3005 (18)0.4892 (12)0.3948 (14)0.093 (14)*0.119 (4)
F2B0.3486 (14)0.4823 (12)0.2764 (15)0.092 (19)*0.119 (4)
F1A0.1634 (3)0.4350 (2)0.23597 (18)0.0307 (8)0.881 (4)
F2A0.2972 (3)0.49270 (15)0.26654 (19)0.0329 (8)0.881 (4)
F3A0.1221 (6)0.51012 (15)0.3023 (2)0.034 (2)0.881 (4)
O1A0.0970 (3)0.4083 (3)0.3952 (3)0.0241 (10)0.881 (4)
O2A0.2888 (3)0.37945 (17)0.3551 (2)0.0284 (9)0.881 (4)
O3A0.2536 (3)0.46808 (16)0.4291 (2)0.0246 (9)0.881 (4)
N1A0.1442 (3)0.46738 (17)0.3768 (2)0.0229 (8)
N2A0.0042 (3)0.53509 (17)0.4579 (2)0.0230 (8)
N3A0.0818 (3)0.43485 (16)0.5559 (2)0.0206 (8)
H3A0.144 (4)0.449 (2)0.541 (3)0.025*
N4A0.1127 (3)0.38621 (16)0.5288 (2)0.0198 (8)
C1A0.2263 (4)0.4357 (2)0.3459 (2)0.0242 (10)
C2A0.2189 (4)0.3726 (2)0.3428 (2)0.0230 (10)
C3A0.1199 (4)0.3420 (2)0.3550 (3)0.0268 (11)
H3AA0.0532650.3626860.3647520.032*
C4A0.1170 (5)0.2822 (2)0.3531 (3)0.0314 (12)
H4A0.0489670.2622960.3617580.038*
C5A0.2147 (5)0.2511 (2)0.3385 (3)0.0342 (12)
H5A0.2139240.2100590.3390040.041*
C6A0.3113 (5)0.2802 (2)0.3235 (3)0.0342 (13)
H6A0.3766370.2588360.3126190.041*
C7A0.3162 (4)0.3412 (2)0.3239 (3)0.0317 (12)
C8A0.4150 (4)0.3714 (3)0.3031 (3)0.0371 (13)
H8A0.4808200.3499950.2931740.044*
C9A0.4164 (5)0.4295 (3)0.2973 (3)0.0408 (14)
H9A0.4805010.4481800.2792750.049*
C10A0.3222 (5)0.4634 (2)0.3181 (3)0.0319 (12)
C11A0.3224 (5)0.5238 (3)0.3122 (3)0.0375 (13)
H11A0.3832160.5429560.2905750.045*
C12A0.2350 (5)0.5550 (2)0.3374 (3)0.0338 (12)
H12A0.2319040.5957920.3310000.041*
C13A0.1504 (4)0.5260 (2)0.3729 (3)0.0261 (11)
C14A0.0658 (4)0.5595 (2)0.4099 (3)0.0261 (10)
H14A0.0560590.5994490.3986540.031*
C15A0.0902 (4)0.56502 (19)0.4856 (3)0.0219 (10)
C16A0.1630 (4)0.59740 (19)0.4338 (3)0.0266 (11)
H16A0.1428960.6028080.3837120.032*
C17A0.2602 (4)0.6203 (2)0.4557 (3)0.0286 (11)
H17A0.3078770.6414030.4203110.034*
C18A0.2928 (4)0.6138 (2)0.5303 (3)0.0259 (10)
C19A0.3957 (4)0.6369 (2)0.5535 (3)0.0315 (12)
H19A0.4448400.6575520.5185380.038*
C20A0.4245 (4)0.6296 (2)0.6254 (3)0.0340 (12)
H20A0.4931610.6455920.6406090.041*
C21A0.3532 (4)0.5988 (2)0.6769 (3)0.0336 (12)
H21A0.3743280.5937850.7268220.040*
C22A0.2541 (4)0.5758 (2)0.6567 (3)0.0254 (10)
H22A0.2071710.5549620.6927540.030*
C23A0.2197 (4)0.58237 (19)0.5825 (3)0.0217 (10)
C24A0.1163 (4)0.55782 (19)0.5587 (3)0.0207 (9)
C25A0.0401 (4)0.5272 (2)0.6162 (2)0.0193 (9)
C26A0.0183 (4)0.5602 (2)0.6746 (2)0.0197 (9)
C27A0.0178 (4)0.6223 (2)0.6739 (3)0.0232 (10)
H27A0.0215130.6423180.6333850.028*
C28A0.0726 (4)0.6526 (2)0.7302 (3)0.0275 (11)
H28A0.0727310.6936400.7281830.033*
C29A0.1296 (4)0.6244 (2)0.7918 (3)0.0295 (11)
H29A0.1655900.6464160.8317090.035*
C30A0.1332 (4)0.5655 (2)0.7943 (3)0.0257 (11)
H30A0.1723470.5466850.8357240.031*
C31A0.0788 (4)0.5322 (2)0.7353 (3)0.0220 (10)
C32A0.0826 (4)0.4708 (2)0.7355 (3)0.0228 (10)
H32A0.1220360.4512170.7763270.027*
C33A0.0308 (4)0.4395 (2)0.6784 (2)0.0225 (10)
H33A0.0361880.3985460.6791220.027*
C34A0.0312 (4)0.4674 (2)0.6179 (2)0.0202 (9)
C35A0.0815 (4)0.37141 (19)0.5611 (3)0.0230 (10)
H35A0.1371920.3551860.5226080.028*
H35B0.1037730.3594010.6111950.028*
C36A0.0354 (4)0.34837 (19)0.5489 (2)0.0224 (10)
C37A0.0612 (4)0.2899 (2)0.5614 (3)0.0282 (11)
H37A0.0051540.2636670.5761180.034*
C38A0.1693 (4)0.2714 (2)0.5518 (3)0.0313 (12)
H38A0.1871520.2314090.5563150.038*
C39A0.2545 (4)0.3115 (2)0.5353 (3)0.0284 (11)
C40A0.3686 (4)0.2939 (2)0.5261 (3)0.0332 (12)
H40A0.3890130.2542750.5304740.040*
C41A0.4472 (5)0.3338 (3)0.5111 (3)0.0379 (14)
H41A0.5214890.3212380.5021620.045*
C42A0.4223 (4)0.3936 (2)0.5082 (3)0.0312 (12)
C43A0.5066 (4)0.4352 (3)0.4960 (3)0.0386 (14)
H43A0.5805110.4226200.4862820.046*
C44A0.4837 (5)0.4929 (3)0.4979 (3)0.0430 (15)
H44A0.5414600.5200910.4891140.052*
C45A0.3751 (5)0.5123 (3)0.5127 (3)0.0362 (13)
H45A0.3602530.5526430.5152520.043*
C46A0.2905 (4)0.4734 (2)0.5236 (3)0.0267 (11)
H46A0.2178260.4870370.5345060.032*
C47A0.3097 (4)0.4134 (2)0.5188 (2)0.0227 (10)
C48A0.2244 (3)0.3701 (2)0.5274 (2)0.0226 (10)
C49A0.1989 (5)0.4679 (2)0.2906 (3)0.0262 (12)0.881 (4)
Cl10.58159 (12)0.61215 (6)0.26355 (8)0.0438 (3)
Cl20.5759 (2)0.73553 (7)0.29120 (10)0.0718 (6)
C520.4935 (5)0.6722 (3)0.2787 (3)0.0453 (14)
H52A0.4377620.6771080.2349830.054*
H52B0.4513320.6654050.3237850.054*
Cl30.0760 (2)0.65839 (12)0.25389 (12)0.1000 (9)
Cl40.0606 (2)0.78324 (10)0.24111 (10)0.0820 (7)
C530.0145 (6)0.7184 (3)0.2463 (4)0.0556 (17)
H53A0.0702640.7193940.2904100.067*
H53B0.0568290.7140860.2006940.067*
Cl50.766 (2)0.3383 (10)0.7706 (14)0.116 (6)0.50 (4)
Cl60.6838 (15)0.4281 (7)0.6701 (10)0.051 (3)0.50 (4)
C540.672 (4)0.3528 (14)0.691 (2)0.078 (14)0.50 (4)
H54A0.5927940.3433860.7017130.094*0.50 (4)
H54B0.6919460.3292290.6475250.094*0.50 (4)
Cl5A0.7225 (10)0.3115 (9)0.7495 (4)0.076 (4)0.50 (4)
Cl6A0.6937 (17)0.4266 (7)0.6793 (10)0.062 (4)0.50 (4)
C54A0.654 (3)0.3534 (9)0.678 (2)0.037 (6)0.50 (4)
H54C0.5712510.3509140.6822580.045*0.50 (4)
H54D0.6702130.3366520.6287930.045*0.50 (4)
S30.26214 (10)0.71026 (5)0.44855 (7)0.0279 (3)
F70.3110 (4)0.7034 (2)0.5944 (2)0.0800 (14)
F80.1374 (3)0.72046 (18)0.5629 (2)0.0651 (11)
F90.2069 (4)0.63445 (17)0.5491 (2)0.0727 (13)
O70.2765 (3)0.77162 (16)0.4520 (2)0.0439 (10)
O80.1623 (3)0.69187 (18)0.4047 (2)0.0445 (10)
O90.3614 (3)0.67666 (19)0.4381 (2)0.0446 (10)
C510.2293 (5)0.6917 (3)0.5441 (3)0.0492 (16)
S20.24274 (11)0.63536 (5)0.11069 (7)0.0278 (3)
F40.1672 (4)0.65490 (19)0.0282 (2)0.0742 (13)
F50.3472 (4)0.6473 (2)0.0134 (2)0.0760 (13)
F60.2426 (3)0.57099 (16)0.0104 (2)0.0601 (10)
O40.2534 (4)0.69671 (15)0.1215 (2)0.0440 (10)
O50.3366 (3)0.60187 (17)0.1411 (2)0.0480 (11)
O60.1339 (3)0.6118 (2)0.1215 (3)0.0539 (11)
C500.2519 (5)0.6268 (3)0.0102 (3)0.0416 (14)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0164 (2)0.0137 (2)0.0242 (3)0.0006 (2)0.00162 (19)0.0021 (2)
S10.0161 (5)0.0186 (6)0.0254 (5)0.0008 (4)0.0008 (4)0.0015 (5)
F10.064 (2)0.0269 (17)0.055 (2)0.0211 (16)0.0039 (17)0.0070 (16)
F20.0262 (15)0.048 (2)0.0407 (17)0.0057 (14)0.0051 (13)0.0107 (15)
F30.0340 (17)0.0387 (19)0.058 (2)0.0033 (14)0.0110 (15)0.0240 (16)
O10.0205 (16)0.0248 (18)0.0381 (19)0.0011 (14)0.0041 (14)0.0048 (15)
O20.0213 (16)0.040 (2)0.0380 (19)0.0007 (16)0.0061 (14)0.0058 (18)
O30.0378 (19)0.0225 (18)0.0302 (18)0.0035 (15)0.0026 (15)0.0044 (14)
N10.0202 (19)0.018 (2)0.0188 (18)0.0003 (15)0.0011 (15)0.0011 (15)
N20.0191 (18)0.0145 (18)0.0217 (17)0.0013 (16)0.0008 (14)0.0014 (16)
N30.0179 (18)0.016 (2)0.032 (2)0.0003 (17)0.0040 (16)0.0043 (18)
N40.024 (2)0.016 (2)0.0233 (19)0.0019 (16)0.0003 (15)0.0009 (16)
C10.020 (2)0.022 (2)0.017 (2)0.0022 (18)0.0003 (17)0.0016 (18)
C20.022 (2)0.016 (2)0.018 (2)0.0040 (18)0.0011 (18)0.0033 (18)
C30.021 (2)0.022 (3)0.031 (3)0.0028 (19)0.001 (2)0.005 (2)
C40.026 (3)0.024 (3)0.040 (3)0.001 (2)0.001 (2)0.010 (2)
C50.035 (3)0.020 (3)0.037 (3)0.000 (2)0.002 (2)0.006 (2)
C60.025 (3)0.024 (3)0.036 (3)0.008 (2)0.003 (2)0.005 (2)
C70.024 (2)0.023 (3)0.022 (2)0.003 (2)0.0021 (19)0.002 (2)
C80.020 (2)0.031 (3)0.033 (3)0.007 (2)0.007 (2)0.006 (2)
C90.021 (2)0.032 (3)0.032 (3)0.001 (2)0.011 (2)0.004 (2)
C100.022 (2)0.026 (3)0.023 (2)0.001 (2)0.0062 (17)0.000 (2)
C110.028 (3)0.031 (3)0.031 (3)0.001 (2)0.013 (2)0.001 (2)
C120.029 (3)0.018 (2)0.029 (2)0.003 (2)0.010 (2)0.002 (2)
C130.020 (2)0.019 (2)0.024 (2)0.0016 (19)0.0002 (18)0.0015 (19)
C140.025 (2)0.014 (2)0.025 (2)0.0026 (19)0.0001 (19)0.0008 (19)
C150.016 (2)0.011 (2)0.028 (2)0.0001 (17)0.0002 (18)0.0022 (18)
C160.029 (3)0.013 (2)0.025 (2)0.0014 (19)0.0039 (19)0.0006 (19)
C170.020 (2)0.015 (2)0.033 (3)0.0024 (19)0.0046 (19)0.001 (2)
C180.021 (2)0.011 (2)0.032 (3)0.0010 (18)0.0016 (19)0.0007 (19)
C190.020 (2)0.014 (2)0.043 (3)0.0001 (18)0.001 (2)0.002 (2)
C200.015 (2)0.020 (3)0.053 (3)0.0034 (19)0.004 (2)0.008 (2)
C210.024 (2)0.026 (3)0.036 (3)0.006 (2)0.010 (2)0.011 (2)
C220.023 (2)0.019 (2)0.032 (3)0.004 (2)0.0023 (19)0.005 (2)
C230.020 (2)0.013 (2)0.033 (2)0.0051 (18)0.0053 (19)0.0062 (19)
C240.018 (2)0.011 (2)0.026 (2)0.0000 (17)0.0002 (18)0.0022 (18)
C250.016 (2)0.022 (2)0.023 (2)0.0033 (19)0.0041 (17)0.0002 (19)
C260.013 (2)0.024 (2)0.024 (2)0.0001 (19)0.0064 (17)0.001 (2)
C270.018 (2)0.027 (3)0.028 (2)0.002 (2)0.0035 (18)0.002 (2)
C280.021 (2)0.030 (3)0.036 (3)0.000 (2)0.001 (2)0.009 (2)
C290.023 (3)0.041 (3)0.034 (3)0.002 (2)0.004 (2)0.015 (2)
C300.021 (2)0.043 (3)0.022 (2)0.000 (2)0.0008 (19)0.005 (2)
C310.021 (2)0.034 (3)0.023 (2)0.002 (2)0.0079 (19)0.001 (2)
C320.025 (2)0.036 (3)0.022 (2)0.004 (2)0.0018 (19)0.006 (2)
C330.030 (3)0.027 (3)0.031 (3)0.005 (2)0.007 (2)0.005 (2)
C340.019 (2)0.025 (3)0.023 (2)0.0012 (19)0.0074 (18)0.0022 (19)
C350.026 (2)0.016 (2)0.034 (3)0.0040 (19)0.006 (2)0.006 (2)
C360.030 (3)0.016 (2)0.024 (2)0.000 (2)0.002 (2)0.0006 (19)
C370.032 (3)0.019 (2)0.033 (3)0.003 (2)0.001 (2)0.004 (2)
C380.043 (3)0.015 (2)0.027 (3)0.006 (2)0.000 (2)0.003 (2)
C390.033 (3)0.019 (2)0.022 (2)0.007 (2)0.0050 (19)0.0006 (19)
C400.039 (3)0.024 (3)0.030 (3)0.012 (2)0.005 (2)0.002 (2)
C410.027 (3)0.033 (3)0.031 (3)0.011 (2)0.004 (2)0.006 (2)
C420.027 (3)0.032 (3)0.021 (2)0.005 (2)0.0018 (19)0.005 (2)
C430.018 (2)0.045 (3)0.036 (3)0.002 (2)0.001 (2)0.012 (3)
C440.024 (3)0.036 (3)0.041 (3)0.006 (2)0.002 (2)0.009 (3)
C450.027 (3)0.023 (3)0.037 (3)0.003 (2)0.002 (2)0.008 (2)
C460.024 (2)0.024 (3)0.023 (2)0.005 (2)0.0020 (19)0.0047 (19)
C470.024 (2)0.023 (2)0.019 (2)0.001 (2)0.0021 (18)0.0046 (19)
C480.022 (2)0.019 (2)0.020 (2)0.0044 (19)0.0015 (18)0.0016 (19)
C490.025 (3)0.027 (3)0.035 (3)0.006 (2)0.004 (2)0.004 (2)
Zn1A0.0228 (3)0.0172 (3)0.0216 (2)0.0004 (2)0.0015 (2)0.0015 (2)
S1A0.0182 (7)0.0222 (7)0.0202 (6)0.0023 (5)0.0003 (5)0.0024 (5)
F1A0.0333 (18)0.036 (2)0.0239 (16)0.0029 (19)0.0075 (14)0.0064 (16)
F2A0.036 (2)0.0283 (19)0.0333 (18)0.0085 (17)0.0054 (16)0.0015 (15)
F3A0.043 (2)0.030 (3)0.028 (3)0.0183 (16)0.0003 (15)0.0001 (14)
O1A0.020 (2)0.027 (2)0.025 (2)0.0004 (18)0.0012 (16)0.002 (2)
O2A0.026 (2)0.028 (2)0.030 (2)0.0095 (18)0.0012 (16)0.0027 (17)
O3A0.0201 (19)0.028 (2)0.0259 (19)0.0029 (16)0.0045 (15)0.0077 (16)
N1A0.030 (2)0.022 (2)0.0171 (18)0.0005 (17)0.0033 (16)0.0027 (16)
N2A0.028 (2)0.019 (2)0.0209 (19)0.0006 (17)0.0020 (16)0.0047 (16)
N3A0.0195 (19)0.018 (2)0.0243 (19)0.0005 (16)0.0011 (16)0.0007 (16)
N4A0.0222 (19)0.0180 (19)0.0193 (18)0.0006 (16)0.0015 (15)0.0037 (15)
C1A0.027 (2)0.028 (3)0.017 (2)0.000 (2)0.0024 (18)0.0004 (19)
C2A0.026 (2)0.023 (3)0.020 (2)0.003 (2)0.0022 (18)0.0051 (19)
C3A0.031 (3)0.024 (3)0.025 (2)0.003 (2)0.003 (2)0.008 (2)
C4A0.036 (3)0.028 (3)0.030 (3)0.003 (2)0.001 (2)0.010 (2)
C5A0.045 (3)0.025 (3)0.033 (3)0.006 (2)0.002 (2)0.008 (2)
C6A0.038 (3)0.036 (3)0.029 (3)0.015 (3)0.005 (2)0.007 (2)
C7A0.033 (3)0.038 (3)0.024 (2)0.004 (2)0.005 (2)0.004 (2)
C8A0.033 (3)0.045 (4)0.035 (3)0.008 (3)0.014 (2)0.006 (3)
C9A0.034 (3)0.051 (4)0.040 (3)0.004 (3)0.017 (2)0.008 (3)
C10A0.041 (3)0.032 (3)0.024 (2)0.001 (2)0.009 (2)0.003 (2)
C11A0.039 (3)0.042 (3)0.034 (3)0.011 (3)0.017 (2)0.004 (3)
C12A0.044 (3)0.028 (3)0.031 (3)0.010 (2)0.009 (2)0.001 (2)
C13A0.035 (3)0.024 (3)0.020 (2)0.005 (2)0.003 (2)0.001 (2)
C14A0.031 (3)0.021 (2)0.026 (2)0.003 (2)0.000 (2)0.000 (2)
C15A0.021 (2)0.015 (2)0.030 (2)0.0022 (18)0.0004 (19)0.0025 (19)
C16A0.039 (3)0.014 (2)0.026 (2)0.001 (2)0.002 (2)0.002 (2)
C17A0.030 (3)0.015 (2)0.039 (3)0.002 (2)0.009 (2)0.001 (2)
C18A0.026 (2)0.014 (2)0.037 (3)0.002 (2)0.005 (2)0.002 (2)
C19A0.021 (2)0.023 (3)0.050 (3)0.004 (2)0.004 (2)0.005 (2)
C20A0.024 (3)0.025 (3)0.054 (3)0.001 (2)0.009 (2)0.000 (2)
C21A0.024 (3)0.036 (3)0.042 (3)0.001 (2)0.009 (2)0.000 (2)
C22A0.022 (2)0.019 (2)0.035 (3)0.0002 (19)0.001 (2)0.001 (2)
C23A0.021 (2)0.013 (2)0.030 (2)0.0022 (18)0.0013 (19)0.0028 (19)
C24A0.022 (2)0.013 (2)0.026 (2)0.0009 (18)0.0017 (18)0.0019 (19)
C25A0.017 (2)0.019 (2)0.022 (2)0.0028 (18)0.0040 (17)0.0024 (19)
C26A0.018 (2)0.022 (2)0.021 (2)0.0015 (18)0.0058 (17)0.0014 (19)
C27A0.020 (2)0.025 (3)0.026 (2)0.0008 (19)0.0055 (18)0.004 (2)
C28A0.029 (3)0.019 (2)0.036 (3)0.003 (2)0.008 (2)0.008 (2)
C29A0.025 (2)0.036 (3)0.027 (2)0.005 (2)0.000 (2)0.015 (2)
C30A0.018 (2)0.037 (3)0.022 (2)0.001 (2)0.0002 (18)0.001 (2)
C31A0.016 (2)0.027 (3)0.023 (2)0.0001 (19)0.0070 (18)0.003 (2)
C32A0.018 (2)0.027 (3)0.024 (2)0.0008 (19)0.0009 (18)0.003 (2)
C33A0.020 (2)0.020 (3)0.029 (2)0.0029 (19)0.0076 (18)0.003 (2)
C34A0.020 (2)0.021 (2)0.021 (2)0.0039 (18)0.0068 (18)0.0036 (18)
C35A0.025 (2)0.015 (2)0.029 (2)0.0066 (19)0.0028 (19)0.000 (2)
C36A0.027 (2)0.019 (2)0.021 (2)0.0040 (19)0.0018 (18)0.0018 (19)
C37A0.035 (3)0.021 (3)0.029 (3)0.006 (2)0.005 (2)0.000 (2)
C38A0.040 (3)0.021 (3)0.032 (3)0.003 (2)0.002 (2)0.001 (2)
C39A0.034 (3)0.028 (3)0.023 (2)0.008 (2)0.001 (2)0.006 (2)
C40A0.032 (3)0.037 (3)0.031 (3)0.013 (2)0.002 (2)0.001 (2)
C41A0.026 (3)0.057 (4)0.031 (3)0.014 (3)0.003 (2)0.004 (3)
C42A0.031 (3)0.042 (3)0.020 (2)0.001 (2)0.001 (2)0.004 (2)
C43A0.021 (2)0.056 (4)0.039 (3)0.005 (3)0.005 (2)0.009 (3)
C44A0.035 (3)0.056 (4)0.039 (3)0.019 (3)0.008 (2)0.014 (3)
C45A0.041 (3)0.038 (3)0.031 (3)0.016 (3)0.006 (2)0.010 (2)
C46A0.024 (3)0.035 (3)0.021 (2)0.007 (2)0.0039 (19)0.006 (2)
C47A0.023 (2)0.030 (3)0.015 (2)0.002 (2)0.0007 (18)0.0058 (19)
C48A0.019 (2)0.027 (3)0.021 (2)0.002 (2)0.0001 (17)0.002 (2)
C49A0.030 (3)0.022 (3)0.026 (3)0.001 (2)0.003 (2)0.004 (2)
Cl10.0474 (8)0.0329 (7)0.0511 (8)0.0016 (6)0.0038 (7)0.0014 (6)
Cl20.1357 (18)0.0293 (8)0.0479 (9)0.0008 (10)0.0115 (10)0.0003 (7)
C520.052 (4)0.047 (4)0.038 (3)0.010 (3)0.005 (3)0.002 (3)
Cl30.1141 (18)0.125 (2)0.0597 (12)0.0453 (16)0.0013 (12)0.0457 (13)
Cl40.1173 (17)0.0904 (16)0.0369 (9)0.0320 (13)0.0048 (10)0.0103 (10)
C530.057 (4)0.070 (5)0.039 (3)0.004 (4)0.000 (3)0.012 (3)
Cl50.129 (10)0.105 (9)0.117 (8)0.056 (8)0.044 (9)0.051 (7)
Cl60.045 (4)0.056 (6)0.052 (4)0.003 (4)0.009 (3)0.007 (4)
C540.08 (2)0.061 (19)0.10 (3)0.029 (14)0.07 (2)0.027 (14)
Cl5A0.070 (5)0.111 (8)0.048 (3)0.046 (4)0.021 (2)0.022 (3)
Cl6A0.069 (7)0.056 (7)0.063 (6)0.025 (5)0.031 (5)0.035 (5)
C54A0.044 (10)0.031 (12)0.038 (8)0.014 (9)0.009 (8)0.001 (8)
S30.0268 (6)0.0253 (7)0.0321 (6)0.0048 (5)0.0046 (5)0.0052 (5)
F70.083 (3)0.116 (4)0.038 (2)0.036 (3)0.015 (2)0.008 (2)
F80.064 (2)0.078 (3)0.058 (2)0.031 (2)0.0326 (19)0.017 (2)
F90.106 (3)0.048 (2)0.069 (3)0.016 (2)0.037 (2)0.029 (2)
O70.048 (2)0.028 (2)0.057 (3)0.0015 (18)0.009 (2)0.0033 (19)
O80.044 (2)0.040 (2)0.048 (2)0.0005 (19)0.0057 (19)0.0010 (19)
O90.037 (2)0.055 (3)0.043 (2)0.020 (2)0.0119 (17)0.003 (2)
C510.048 (4)0.056 (4)0.045 (4)0.024 (3)0.013 (3)0.006 (3)
S20.0325 (7)0.0196 (6)0.0313 (6)0.0007 (5)0.0032 (5)0.0001 (5)
F40.093 (3)0.083 (3)0.043 (2)0.035 (3)0.017 (2)0.001 (2)
F50.076 (3)0.099 (4)0.057 (2)0.019 (3)0.034 (2)0.009 (2)
F60.075 (3)0.052 (2)0.051 (2)0.012 (2)0.0135 (18)0.0237 (18)
O40.062 (3)0.0195 (19)0.051 (2)0.0061 (18)0.005 (2)0.0048 (18)
O50.059 (3)0.038 (2)0.043 (2)0.020 (2)0.0187 (19)0.0133 (19)
O60.046 (2)0.052 (3)0.066 (3)0.016 (2)0.018 (2)0.002 (2)
C500.048 (3)0.039 (3)0.037 (3)0.002 (3)0.001 (3)0.004 (3)
Geometric parameters (Å, º) top
Zn1—O12.028 (3)F3A—C49A1.340 (7)
Zn1—N12.160 (4)N1A—C1A1.365 (6)
Zn1—N22.056 (4)N1A—C13A1.361 (6)
Zn1—N32.253 (4)N2A—C14A1.295 (6)
Zn1—N42.059 (4)N2A—C15A1.433 (6)
S1—O11.473 (3)N3A—H3A0.83 (5)
S1—O21.428 (3)N3A—C34A1.432 (6)
S1—O31.426 (3)N3A—C35A1.470 (6)
S1—C491.829 (5)N4A—C36A1.334 (6)
F1—C491.318 (6)N4A—C48A1.376 (5)
F2—C491.339 (6)C1A—C2A1.463 (7)
F3—C491.321 (6)C1A—C10A1.424 (7)
N1—C11.362 (6)C2A—C3A1.400 (7)
N1—C131.354 (6)C2A—C7A1.422 (7)
N2—C141.281 (6)C3A—H3AA0.9500
N2—C151.439 (5)C3A—C4A1.382 (7)
N3—H30.82 (5)C4A—H4A0.9500
N3—C341.433 (6)C4A—C5A1.403 (7)
N3—C351.473 (6)C5A—H5A0.9500
N4—C361.337 (6)C5A—C6A1.369 (8)
N4—C481.377 (6)C6A—H6A0.9500
C1—C21.453 (6)C6A—C7A1.410 (8)
C1—C101.422 (6)C7A—C8A1.435 (7)
C2—C31.399 (6)C8A—H8A0.9500
C2—C71.418 (6)C8A—C9A1.348 (8)
C3—H3B0.9500C9A—H9A0.9500
C3—C41.373 (7)C9A—C10A1.434 (8)
C4—H40.9500C10A—C11A1.401 (8)
C4—C51.402 (7)C11A—H11A0.9500
C5—H50.9500C11A—C12A1.365 (8)
C5—C61.374 (7)C12A—H12A0.9500
C6—H60.9500C12A—C13A1.394 (7)
C6—C71.403 (7)C13A—C14A1.460 (7)
C7—C81.439 (7)C14A—H14A0.9500
C8—H80.9500C15A—C16A1.429 (6)
C8—C91.338 (7)C15A—C24A1.370 (6)
C9—H90.9500C16A—H16A0.9500
C9—C101.442 (6)C16A—C17A1.349 (7)
C10—C111.408 (7)C17A—H17A0.9500
C11—H110.9500C17A—C18A1.420 (7)
C11—C121.377 (7)C18A—C19A1.419 (7)
C12—H120.9500C18A—C23A1.423 (6)
C12—C131.393 (6)C19A—H19A0.9500
C13—C141.476 (6)C19A—C20A1.362 (8)
C14—H140.9500C20A—H20A0.9500
C15—C161.408 (6)C20A—C21A1.397 (7)
C15—C241.369 (6)C21A—H21A0.9500
C16—H160.9500C21A—C22A1.360 (7)
C16—C171.360 (6)C22A—H22A0.9500
C17—H170.9500C22A—C23A1.421 (7)
C17—C181.412 (7)C23A—C24A1.441 (6)
C18—C191.425 (6)C24A—C25A1.495 (6)
C18—C231.428 (6)C25A—C26A1.427 (6)
C19—H190.9500C25A—C34A1.388 (6)
C19—C201.365 (7)C26A—C27A1.437 (6)
C20—H200.9500C26A—C31A1.413 (6)
C20—C211.407 (7)C27A—H27A0.9500
C21—H210.9500C27A—C28A1.352 (7)
C21—C221.377 (7)C28A—H28A0.9500
C22—H220.9500C28A—C29A1.407 (7)
C22—C231.420 (7)C29A—H29A0.9500
C23—C241.438 (6)C29A—C30A1.362 (7)
C24—C251.499 (6)C30A—H30A0.9500
C25—C261.430 (6)C30A—C31A1.420 (6)
C25—C341.381 (7)C31A—C32A1.420 (7)
C26—C271.414 (7)C32A—H32A0.9500
C26—C311.415 (6)C32A—C33A1.358 (6)
C27—H270.9500C33A—H33A0.9500
C27—C281.376 (7)C33A—C34A1.415 (6)
C28—H280.9500C35A—H35A0.9900
C28—C291.402 (7)C35A—H35B0.9900
C29—H290.9500C35A—C36A1.513 (6)
C29—C301.364 (7)C36A—C37A1.401 (7)
C30—H300.9500C37A—H37A0.9500
C30—C311.421 (7)C37A—C38A1.372 (7)
C31—C321.417 (7)C38A—H38A0.9500
C32—H320.9500C38A—C39A1.416 (7)
C32—C331.366 (7)C39A—C40A1.432 (7)
C33—H330.9500C39A—C48A1.407 (7)
C33—C341.403 (6)C40A—H40A0.9500
C35—H35C0.9900C40A—C41A1.350 (8)
C35—H35D0.9900C41A—H41A0.9500
C35—C361.514 (7)C41A—C42A1.416 (8)
C36—C371.401 (7)C42A—C43A1.413 (8)
C37—H370.9500C42A—C47A1.435 (7)
C37—C381.368 (7)C43A—H43A0.9500
C38—H380.9500C43A—C44A1.363 (9)
C38—C391.409 (7)C44A—H44A0.9500
C39—C401.440 (7)C44A—C45A1.405 (8)
C39—C481.404 (6)C45A—H45A0.9500
C40—H400.9500C45A—C46A1.372 (7)
C40—C411.342 (7)C46A—H46A0.9500
C41—H410.9500C46A—C47A1.410 (7)
C41—C421.440 (7)C47A—C48A1.437 (6)
C42—C431.415 (7)Cl1—C521.770 (6)
C42—C471.406 (7)Cl2—C521.764 (7)
C43—H430.9500C52—H52A0.9900
C43—C441.361 (8)C52—H52B0.9900
C44—H440.9500Cl3—C531.765 (7)
C44—C451.406 (7)Cl4—C531.743 (7)
C45—H450.9500C53—H53A0.9900
C45—C461.378 (7)C53—H53B0.9900
C46—H460.9500Cl5—C541.77 (4)
C46—C471.416 (7)Cl6—C541.79 (3)
C47—C481.447 (6)C54—H54A0.9900
Zn1A—O1B1.994 (19)C54—H54B0.9900
Zn1A—O1A2.045 (4)Cl5A—C54A1.75 (2)
Zn1A—N1A2.165 (4)Cl6A—C54A1.76 (2)
Zn1A—N2A2.042 (4)C54A—H54C0.9900
Zn1A—N3A2.219 (4)C54A—H54D0.9900
Zn1A—N4A2.068 (4)S3—O71.430 (4)
S1A—O1A1.472 (4)S3—O81.434 (4)
S1A—O2A1.426 (4)S3—O91.432 (4)
S1A—O3A1.447 (4)S3—C511.827 (6)
S1A—C49A1.827 (6)F7—C511.299 (8)
S1B—O2B1.4453F8—C511.338 (7)
S1B—O3B1.4440F9—C511.355 (8)
S1B—O1B1.4452S2—O41.436 (4)
S1B—C49B1.8517S2—O51.429 (4)
C49B—F3B1.3392S2—O61.424 (4)
C49B—F1B1.3389S2—C501.815 (6)
C49B—F2B1.3388F4—C501.341 (7)
F1A—C49A1.328 (6)F5—C501.320 (7)
F2A—C49A1.341 (7)F6—C501.343 (7)
O1—Zn1—N1103.31 (14)S1A—O1A—Zn1A130.0 (3)
O1—Zn1—N2107.79 (14)C1A—N1A—Zn1A132.5 (3)
O1—Zn1—N382.47 (14)C13A—N1A—Zn1A106.6 (3)
O1—Zn1—N4105.35 (14)C13A—N1A—C1A118.2 (4)
N1—Zn1—N3172.38 (14)C14A—N2A—Zn1A111.7 (3)
N2—Zn1—N180.55 (14)C14A—N2A—C15A120.6 (4)
N2—Zn1—N393.01 (14)C15A—N2A—Zn1A125.3 (3)
N2—Zn1—N4143.22 (14)Zn1A—N3A—H3A105 (3)
N4—Zn1—N1106.87 (14)C34A—N3A—Zn1A106.2 (3)
N4—Zn1—N375.90 (15)C34A—N3A—H3A111 (4)
O1—S1—C4998.8 (2)C34A—N3A—C35A118.5 (4)
O2—S1—O1112.5 (2)C35A—N3A—Zn1A100.5 (3)
O2—S1—C49105.8 (2)C35A—N3A—H3A114 (4)
O3—S1—O1112.5 (2)C36A—N4A—Zn1A107.1 (3)
O3—S1—O2118.7 (2)C36A—N4A—C48A120.5 (4)
O3—S1—C49106.1 (2)C48A—N4A—Zn1A126.8 (3)
S1—O1—Zn1126.6 (2)N1A—C1A—C2A120.6 (4)
C1—N1—Zn1130.5 (3)N1A—C1A—C10A120.5 (4)
C13—N1—Zn1108.0 (3)C10A—C1A—C2A118.9 (4)
C13—N1—C1117.9 (4)C3A—C2A—C1A123.1 (4)
C14—N2—Zn1112.8 (3)C3A—C2A—C7A118.7 (5)
C14—N2—C15120.9 (4)C7A—C2A—C1A118.1 (4)
C15—N2—Zn1123.7 (3)C2A—C3A—H3AA119.3
Zn1—N3—H3105 (4)C4A—C3A—C2A121.4 (5)
C34—N3—Zn1103.6 (3)C4A—C3A—H3AA119.3
C34—N3—H3112 (4)C3A—C4A—H4A120.1
C34—N3—C35119.4 (4)C3A—C4A—C5A119.8 (5)
C35—N3—Zn1101.5 (3)C5A—C4A—H4A120.1
C35—N3—H3113 (4)C4A—C5A—H5A120.1
C36—N4—Zn1108.8 (3)C6A—C5A—C4A119.7 (5)
C36—N4—C48119.7 (4)C6A—C5A—H5A120.1
C48—N4—Zn1125.4 (3)C5A—C6A—H6A119.2
N1—C1—C2120.1 (4)C5A—C6A—C7A121.6 (5)
N1—C1—C10120.8 (4)C7A—C6A—H6A119.2
C10—C1—C2119.1 (4)C2A—C7A—C8A120.1 (5)
C3—C2—C1122.6 (4)C6A—C7A—C2A118.6 (5)
C3—C2—C7118.8 (4)C6A—C7A—C8A121.3 (5)
C7—C2—C1118.6 (4)C7A—C8A—H8A119.3
C2—C3—H3B119.4C9A—C8A—C7A121.3 (5)
C4—C3—C2121.3 (4)C9A—C8A—H8A119.3
C4—C3—H3B119.4C8A—C9A—H9A119.6
C3—C4—H4119.9C8A—C9A—C10A120.8 (5)
C3—C4—C5120.2 (5)C10A—C9A—H9A119.6
C5—C4—H4119.9C1A—C10A—C9A119.9 (5)
C4—C5—H5120.3C11A—C10A—C1A118.8 (5)
C6—C5—C4119.4 (5)C11A—C10A—C9A121.3 (5)
C6—C5—H5120.3C10A—C11A—H11A120.1
C5—C6—H6119.2C12A—C11A—C10A119.8 (5)
C5—C6—C7121.6 (4)C12A—C11A—H11A120.1
C7—C6—H6119.2C11A—C12A—H12A120.6
C2—C7—C8119.5 (4)C11A—C12A—C13A118.8 (5)
C6—C7—C2118.6 (4)C13A—C12A—H12A120.6
C6—C7—C8121.8 (4)N1A—C13A—C12A123.1 (5)
C7—C8—H8119.1N1A—C13A—C14A117.6 (4)
C9—C8—C7121.8 (4)C12A—C13A—C14A119.2 (5)
C9—C8—H8119.1N2A—C14A—C13A120.4 (4)
C8—C9—H9119.7N2A—C14A—H14A119.8
C8—C9—C10120.6 (5)C13A—C14A—H14A119.8
C10—C9—H9119.7C16A—C15A—N2A118.6 (4)
C1—C10—C9119.4 (4)C24A—C15A—N2A120.3 (4)
C11—C10—C1118.5 (4)C24A—C15A—C16A120.7 (4)
C11—C10—C9122.1 (4)C15A—C16A—H16A119.8
C10—C11—H11120.0C17A—C16A—C15A120.4 (5)
C12—C11—C10120.0 (4)C17A—C16A—H16A119.8
C12—C11—H11120.0C16A—C17A—H17A119.2
C11—C12—H12121.1C16A—C17A—C18A121.6 (5)
C11—C12—C13117.8 (4)C18A—C17A—H17A119.2
C13—C12—H12121.1C17A—C18A—C23A118.2 (4)
N1—C13—C12124.2 (4)C19A—C18A—C17A122.0 (4)
N1—C13—C14115.7 (4)C19A—C18A—C23A119.7 (5)
C12—C13—C14120.2 (4)C18A—C19A—H19A119.8
N2—C14—C13119.6 (4)C20A—C19A—C18A120.5 (5)
N2—C14—H14120.2C20A—C19A—H19A119.8
C13—C14—H14120.2C19A—C20A—H20A120.0
C16—C15—N2118.6 (4)C19A—C20A—C21A120.1 (5)
C24—C15—N2119.3 (4)C21A—C20A—H20A120.0
C24—C15—C16121.8 (4)C20A—C21A—H21A119.4
C15—C16—H16120.0C22A—C21A—C20A121.2 (5)
C17—C16—C15120.1 (4)C22A—C21A—H21A119.4
C17—C16—H16120.0C21A—C22A—H22A119.5
C16—C17—H17119.5C21A—C22A—C23A121.0 (5)
C16—C17—C18121.1 (4)C23A—C22A—H22A119.5
C18—C17—H17119.5C18A—C23A—C24A119.9 (4)
C17—C18—C19121.9 (4)C22A—C23A—C18A117.5 (4)
C17—C18—C23118.9 (4)C22A—C23A—C24A122.6 (4)
C19—C18—C23119.1 (4)C15A—C24A—C23A119.1 (4)
C18—C19—H19119.7C15A—C24A—C25A122.9 (4)
C20—C19—C18120.7 (5)C23A—C24A—C25A117.9 (4)
C20—C19—H19119.7C26A—C25A—C24A119.0 (4)
C19—C20—H20119.7C34A—C25A—C24A121.8 (4)
C19—C20—C21120.6 (4)C34A—C25A—C26A119.0 (4)
C21—C20—H20119.7C25A—C26A—C27A121.7 (4)
C20—C21—H21119.9C31A—C26A—C25A120.4 (4)
C22—C21—C20120.1 (5)C31A—C26A—C27A117.9 (4)
C22—C21—H21119.9C26A—C27A—H27A119.7
C21—C22—H22119.4C28A—C27A—C26A120.6 (5)
C21—C22—C23121.2 (5)C28A—C27A—H27A119.7
C23—C22—H22119.4C27A—C28A—H28A119.4
C18—C23—C24119.2 (4)C27A—C28A—C29A121.2 (5)
C22—C23—C18118.2 (4)C29A—C28A—H28A119.4
C22—C23—C24122.6 (4)C28A—C29A—H29A120.0
C15—C24—C23118.8 (4)C30A—C29A—C28A120.0 (4)
C15—C24—C25122.4 (4)C30A—C29A—H29A120.0
C23—C24—C25118.7 (4)C29A—C30A—H30A119.7
C26—C25—C24119.5 (4)C29A—C30A—C31A120.6 (5)
C34—C25—C24120.5 (4)C31A—C30A—H30A119.7
C34—C25—C26119.9 (4)C26A—C31A—C30A119.7 (4)
C27—C26—C25122.7 (4)C26A—C31A—C32A118.3 (4)
C27—C26—C31118.2 (4)C30A—C31A—C32A122.0 (4)
C31—C26—C25119.1 (4)C31A—C32A—H32A119.4
C26—C27—H27119.6C33A—C32A—C31A121.2 (4)
C28—C27—C26120.9 (5)C33A—C32A—H32A119.4
C28—C27—H27119.6C32A—C33A—H33A119.6
C27—C28—H28119.8C32A—C33A—C34A120.7 (4)
C27—C28—C29120.5 (5)C34A—C33A—H33A119.6
C29—C28—H28119.8C25A—C34A—N3A118.7 (4)
C28—C29—H29119.9C25A—C34A—C33A120.3 (4)
C30—C29—C28120.2 (5)C33A—C34A—N3A121.0 (4)
C30—C29—H29119.9N3A—C35A—H35A109.7
C29—C30—H30119.7N3A—C35A—H35B109.7
C29—C30—C31120.5 (5)N3A—C35A—C36A109.9 (4)
C31—C30—H30119.7H35A—C35A—H35B108.2
C26—C31—C30119.6 (5)C36A—C35A—H35A109.7
C26—C31—C32118.9 (5)C36A—C35A—H35B109.7
C32—C31—C30121.4 (5)N4A—C36A—C35A117.4 (4)
C31—C32—H32119.5N4A—C36A—C37A122.0 (4)
C33—C32—C31121.1 (5)C37A—C36A—C35A120.6 (4)
C33—C32—H32119.5C36A—C37A—H37A120.8
C32—C33—H33119.8C38A—C37A—C36A118.5 (5)
C32—C33—C34120.4 (5)C38A—C37A—H37A120.8
C34—C33—H33119.8C37A—C38A—H38A119.8
C25—C34—N3118.4 (4)C37A—C38A—C39A120.4 (5)
C25—C34—C33120.5 (4)C39A—C38A—H38A119.8
C33—C34—N3120.9 (4)C38A—C39A—C40A122.0 (5)
N3—C35—H35C109.5C48A—C39A—C38A118.3 (4)
N3—C35—H35D109.5C48A—C39A—C40A119.7 (5)
N3—C35—C36110.6 (4)C39A—C40A—H40A120.0
H35C—C35—H35D108.1C41A—C40A—C39A120.0 (5)
C36—C35—H35C109.5C41A—C40A—H40A120.0
C36—C35—H35D109.5C40A—C41A—H41A119.0
N4—C36—C35117.4 (4)C40A—C41A—C42A122.0 (5)
N4—C36—C37121.7 (4)C42A—C41A—H41A119.0
C37—C36—C35120.8 (4)C41A—C42A—C47A120.0 (5)
C36—C37—H37120.6C43A—C42A—C41A121.5 (5)
C38—C37—C36118.8 (5)C43A—C42A—C47A118.5 (5)
C38—C37—H37120.6C42A—C43A—H43A119.4
C37—C38—H38119.7C44A—C43A—C42A121.2 (5)
C37—C38—C39120.7 (4)C44A—C43A—H43A119.4
C39—C38—H38119.7C43A—C44A—H44A119.9
C38—C39—C40123.2 (4)C43A—C44A—C45A120.3 (5)
C48—C39—C38117.6 (4)C45A—C44A—H44A119.9
C48—C39—C40119.2 (4)C44A—C45A—H45A119.9
C39—C40—H40119.7C46A—C45A—C44A120.2 (5)
C41—C40—C39120.7 (5)C46A—C45A—H45A119.9
C41—C40—H40119.7C45A—C46A—H46A119.5
C40—C41—H41119.4C45A—C46A—C47A121.1 (5)
C40—C41—C42121.1 (5)C47A—C46A—H46A119.5
C42—C41—H41119.4C42A—C47A—C48A117.3 (4)
C43—C42—C41120.6 (5)C46A—C47A—C42A118.5 (5)
C47—C42—C41119.9 (5)C46A—C47A—C48A124.1 (4)
C47—C42—C43119.4 (5)N4A—C48A—C39A119.7 (4)
C42—C43—H43120.0N4A—C48A—C47A119.8 (4)
C44—C43—C42120.0 (5)C39A—C48A—C47A120.5 (4)
C44—C43—H43120.0F1A—C49A—S1A111.8 (4)
C43—C44—H44119.5F1A—C49A—F2A108.9 (4)
C43—C44—C45121.1 (5)F1A—C49A—F3A106.5 (5)
C45—C44—H44119.5F2A—C49A—S1A110.7 (4)
C44—C45—H45120.1F3A—C49A—S1A111.4 (4)
C46—C45—C44119.9 (5)F3A—C49A—F2A107.5 (5)
C46—C45—H45120.1Cl1—C52—H52A109.6
C45—C46—H46120.0Cl1—C52—H52B109.6
C45—C46—C47120.1 (5)Cl2—C52—Cl1110.1 (3)
C47—C46—H46120.0Cl2—C52—H52A109.6
C42—C47—C46119.2 (4)Cl2—C52—H52B109.6
C42—C47—C48118.2 (4)H52A—C52—H52B108.1
C46—C47—C48122.4 (4)Cl3—C53—H53A109.3
N4—C48—C39120.6 (4)Cl3—C53—H53B109.3
N4—C48—C47119.4 (4)Cl4—C53—Cl3111.7 (4)
C39—C48—C47120.0 (4)Cl4—C53—H53A109.3
F1—C49—S1110.4 (3)Cl4—C53—H53B109.3
F1—C49—F2107.8 (4)H53A—C53—H53B107.9
F1—C49—F3108.3 (4)Cl5—C54—Cl6107 (2)
F2—C49—S1110.7 (4)Cl5—C54—H54A110.3
F3—C49—S1111.4 (3)Cl5—C54—H54B110.3
F3—C49—F2108.2 (4)Cl6—C54—H54A110.3
O1B—Zn1A—N1A89.7 (6)Cl6—C54—H54B110.3
O1B—Zn1A—N2A100.0 (7)H54A—C54—H54B108.5
O1B—Zn1A—N3A95.4 (6)Cl5A—C54A—Cl6A114 (2)
O1B—Zn1A—N4A119.7 (7)Cl5A—C54A—H54C108.7
O1A—Zn1A—N1A99.02 (19)Cl5A—C54A—H54D108.7
O1A—Zn1A—N3A86.49 (18)Cl6A—C54A—H54C108.7
O1A—Zn1A—N4A109.2 (2)Cl6A—C54A—H54D108.7
N1A—Zn1A—N3A174.03 (14)H54C—C54A—H54D107.6
N2A—Zn1A—O1A109.05 (19)O7—S3—O8114.1 (2)
N2A—Zn1A—N1A82.08 (15)O7—S3—O9116.6 (3)
N2A—Zn1A—N3A94.00 (15)O7—S3—C51103.0 (3)
N2A—Zn1A—N4A139.56 (14)O8—S3—C51102.5 (3)
N4A—Zn1A—N1A104.21 (15)O9—S3—O8114.8 (3)
N4A—Zn1A—N3A75.87 (15)O9—S3—C51103.1 (3)
O1A—S1A—C49A100.7 (3)F7—C51—S3113.4 (5)
O2A—S1A—O1A113.5 (3)F7—C51—F8107.5 (5)
O2A—S1A—O3A117.6 (2)F7—C51—F9107.4 (5)
O2A—S1A—C49A106.1 (2)F8—C51—S3110.5 (4)
O3A—S1A—O1A112.3 (2)F8—C51—F9107.6 (5)
O3A—S1A—C49A104.5 (2)F9—C51—S3110.2 (4)
O2B—S1B—C49B102.3O4—S2—C50103.3 (3)
O3B—S1B—O2B115.5O5—S2—O4115.2 (3)
O3B—S1B—O1B115.6O5—S2—C50102.5 (3)
O3B—S1B—C49B102.4O6—S2—O4115.5 (3)
O1B—S1B—O2B115.5O6—S2—O5115.3 (3)
O1B—S1B—C49B102.4O6—S2—C50102.2 (3)
S1B—O1B—Zn1A133.2 (14)F4—C50—S2110.8 (4)
F3B—C49B—S1B111.8F4—C50—F6106.5 (5)
F1B—C49B—S1B111.9F5—C50—S2112.9 (4)
F1B—C49B—F3B106.9F5—C50—F4106.7 (5)
F2B—C49B—S1B111.9F5—C50—F6108.2 (5)
F2B—C49B—F3B106.9F6—C50—S2111.4 (4)
F2B—C49B—F1B107.0
Zn1—N1—C1—C231.6 (6)O2B—S1B—C49B—F3B180.0
Zn1—N1—C1—C10147.7 (3)O2B—S1B—C49B—F1B60.0
Zn1—N1—C13—C12160.4 (4)O2B—S1B—C49B—F2B60.0
Zn1—N1—C13—C1419.4 (4)O3B—S1B—O1B—Zn1A133.3 (16)
Zn1—N2—C14—C137.6 (5)O3B—S1B—C49B—F3B60.0
Zn1—N2—C15—C16116.0 (4)O3B—S1B—C49B—F1B180.0
Zn1—N2—C15—C2458.6 (5)O3B—S1B—C49B—F2B59.9
Zn1—N3—C34—C2576.6 (4)O1B—S1B—C49B—F3B60.0
Zn1—N3—C34—C3398.4 (4)O1B—S1B—C49B—F1B60.0
Zn1—N3—C35—C3635.4 (4)O1B—S1B—C49B—F2B180.0
Zn1—N4—C36—C3534.5 (5)C49B—S1B—O1B—Zn1A116.3 (16)
Zn1—N4—C36—C37146.0 (4)O1A—S1A—C49A—F1A63.5 (4)
Zn1—N4—C48—C39137.9 (4)O1A—S1A—C49A—F2A175.0 (4)
Zn1—N4—C48—C4744.4 (5)O1A—S1A—C49A—F3A55.5 (5)
O1—S1—C49—F158.8 (4)O2A—S1A—O1A—Zn1A155.7 (4)
O1—S1—C49—F2178.1 (3)O2A—S1A—C49A—F1A55.0 (4)
O1—S1—C49—F361.5 (4)O2A—S1A—C49A—F2A66.5 (4)
O2—S1—O1—Zn180.9 (3)O2A—S1A—C49A—F3A174.0 (5)
O2—S1—C49—F157.7 (4)O3A—S1A—O1A—Zn1A19.3 (6)
O2—S1—C49—F261.6 (4)O3A—S1A—C49A—F1A180.0 (4)
O2—S1—C49—F3178.0 (3)O3A—S1A—C49A—F2A58.4 (4)
O3—S1—O1—Zn156.3 (3)O3A—S1A—C49A—F3A61.0 (5)
O3—S1—C49—F1175.3 (3)N1A—C1A—C2A—C3A14.3 (7)
O3—S1—C49—F265.4 (4)N1A—C1A—C2A—C7A167.9 (4)
O3—S1—C49—F355.0 (4)N1A—C1A—C10A—C9A169.7 (4)
N1—C1—C2—C314.0 (6)N1A—C1A—C10A—C11A9.9 (7)
N1—C1—C2—C7168.9 (4)N1A—C13A—C14A—N2A14.8 (7)
N1—C1—C10—C9169.6 (4)N2A—C15A—C16A—C17A171.9 (4)
N1—C1—C10—C119.0 (6)N2A—C15A—C24A—C23A172.0 (4)
N1—C13—C14—N219.6 (6)N2A—C15A—C24A—C25A10.2 (7)
N2—C15—C16—C17171.6 (4)N3A—C35A—C36A—N4A6.4 (6)
N2—C15—C24—C23172.0 (4)N3A—C35A—C36A—C37A171.1 (4)
N2—C15—C24—C259.3 (6)N4A—C36A—C37A—C38A0.6 (7)
N3—C35—C36—N44.0 (6)C1A—N1A—C13A—C12A1.4 (7)
N3—C35—C36—C37175.4 (4)C1A—N1A—C13A—C14A176.6 (4)
N4—C36—C37—C380.2 (7)C1A—C2A—C3A—C4A178.6 (4)
C1—N1—C13—C120.6 (6)C1A—C2A—C7A—C6A177.6 (4)
C1—N1—C13—C14179.6 (4)C1A—C2A—C7A—C8A4.7 (7)
C1—C2—C3—C4178.4 (4)C1A—C10A—C11A—C12A4.2 (8)
C1—C2—C7—C6178.3 (4)C2A—C1A—C10A—C9A8.6 (7)
C1—C2—C7—C83.7 (6)C2A—C1A—C10A—C11A171.8 (4)
C1—C10—C11—C122.0 (7)C2A—C3A—C4A—C5A0.2 (7)
C2—C1—C10—C99.7 (6)C2A—C7A—C8A—C9A3.3 (8)
C2—C1—C10—C11171.7 (4)C3A—C2A—C7A—C6A4.4 (7)
C2—C3—C4—C51.2 (8)C3A—C2A—C7A—C8A173.2 (4)
C2—C7—C8—C94.2 (7)C3A—C4A—C5A—C6A2.3 (8)
C3—C2—C7—C64.5 (7)C4A—C5A—C6A—C7A1.4 (8)
C3—C2—C7—C8173.5 (4)C5A—C6A—C7A—C2A2.0 (8)
C3—C4—C5—C62.2 (8)C5A—C6A—C7A—C8A175.6 (5)
C4—C5—C6—C72.2 (8)C6A—C7A—C8A—C9A174.4 (5)
C5—C6—C7—C21.2 (7)C7A—C2A—C3A—C4A3.6 (7)
C5—C6—C7—C8176.8 (5)C7A—C8A—C9A—C10A5.4 (9)
C6—C7—C8—C9173.7 (5)C8A—C9A—C10A—C1A0.6 (8)
C7—C2—C3—C44.5 (7)C8A—C9A—C10A—C11A179.8 (5)
C7—C8—C9—C105.1 (8)C9A—C10A—C11A—C12A175.3 (5)
C8—C9—C10—C11.9 (7)C10A—C1A—C2A—C3A167.4 (4)
C8—C9—C10—C11179.5 (5)C10A—C1A—C2A—C7A10.4 (6)
C9—C10—C11—C12176.6 (4)C10A—C11A—C12A—C13A3.8 (8)
C10—C1—C2—C3166.7 (4)C11A—C12A—C13A—N1A6.9 (8)
C10—C1—C2—C710.4 (6)C11A—C12A—C13A—C14A171.0 (5)
C10—C11—C12—C135.2 (7)C12A—C13A—C14A—N2A163.2 (4)
C11—C12—C13—N16.2 (7)C13A—N1A—C1A—C2A174.7 (4)
C11—C12—C13—C14173.6 (4)C13A—N1A—C1A—C10A7.0 (6)
C12—C13—C14—N2160.2 (4)C14A—N2A—C15A—C16A42.5 (6)
C13—N1—C1—C2172.5 (4)C14A—N2A—C15A—C24A144.0 (4)
C13—N1—C1—C108.2 (6)C15A—N2A—C14A—C13A170.4 (4)
C14—N2—C15—C1644.5 (6)C15A—C16A—C17A—C18A0.6 (7)
C14—N2—C15—C24140.8 (4)C15A—C24A—C25A—C26A108.6 (5)
C15—N2—C14—C13170.1 (4)C15A—C24A—C25A—C34A76.5 (6)
C15—C16—C17—C181.3 (7)C16A—C15A—C24A—C23A1.2 (7)
C15—C24—C25—C26104.5 (5)C16A—C15A—C24A—C25A176.5 (4)
C15—C24—C25—C3477.8 (6)C16A—C17A—C18A—C19A178.9 (4)
C16—C15—C24—C232.4 (6)C16A—C17A—C18A—C23A0.4 (7)
C16—C15—C24—C25176.2 (4)C17A—C18A—C19A—C20A179.9 (5)
C16—C17—C18—C19178.3 (4)C17A—C18A—C23A—C22A179.5 (4)
C16—C17—C18—C230.6 (7)C17A—C18A—C23A—C24A0.7 (7)
C17—C18—C19—C20179.6 (4)C18A—C19A—C20A—C21A0.6 (8)
C17—C18—C23—C22179.2 (4)C18A—C23A—C24A—C15A0.2 (7)
C17—C18—C23—C241.0 (6)C18A—C23A—C24A—C25A177.7 (4)
C18—C19—C20—C212.1 (7)C19A—C18A—C23A—C22A0.1 (7)
C18—C23—C24—C150.5 (6)C19A—C18A—C23A—C24A178.7 (4)
C18—C23—C24—C25178.3 (4)C19A—C20A—C21A—C22A0.4 (8)
C19—C18—C23—C220.2 (6)C20A—C21A—C22A—C23A0.0 (8)
C19—C18—C23—C24177.9 (4)C21A—C22A—C23A—C18A0.2 (7)
C19—C20—C21—C221.5 (7)C21A—C22A—C23A—C24A178.9 (4)
C20—C21—C22—C230.3 (7)C22A—C23A—C24A—C15A178.6 (4)
C21—C22—C23—C180.3 (7)C22A—C23A—C24A—C25A3.6 (6)
C21—C22—C23—C24178.4 (4)C23A—C18A—C19A—C20A0.5 (7)
C22—C23—C24—C15177.6 (4)C23A—C24A—C25A—C26A69.2 (5)
C22—C23—C24—C253.7 (6)C23A—C24A—C25A—C34A105.8 (5)
C23—C18—C19—C201.4 (7)C24A—C15A—C16A—C17A1.5 (7)
C23—C24—C25—C2674.2 (5)C24A—C25A—C26A—C27A8.4 (6)
C23—C24—C25—C34103.5 (5)C24A—C25A—C26A—C31A171.5 (4)
C24—C15—C16—C172.9 (7)C24A—C25A—C34A—N3A10.4 (6)
C24—C25—C26—C276.4 (6)C24A—C25A—C34A—C33A172.2 (4)
C24—C25—C26—C31174.5 (4)C25A—C26A—C27A—C28A179.2 (4)
C24—C25—C34—N38.6 (6)C25A—C26A—C31A—C30A177.8 (4)
C24—C25—C34—C33176.4 (4)C25A—C26A—C31A—C32A1.8 (6)
C25—C26—C27—C28179.8 (4)C26A—C25A—C34A—N3A174.6 (4)
C25—C26—C31—C30178.7 (4)C26A—C25A—C34A—C33A2.7 (6)
C25—C26—C31—C322.7 (6)C26A—C27A—C28A—C29A1.4 (7)
C26—C25—C34—N3173.7 (4)C26A—C31A—C32A—C33A0.8 (7)
C26—C25—C34—C331.3 (6)C27A—C26A—C31A—C30A2.1 (6)
C26—C27—C28—C292.1 (7)C27A—C26A—C31A—C32A178.3 (4)
C26—C31—C32—C330.4 (7)C27A—C28A—C29A—C30A2.1 (7)
C27—C26—C31—C302.2 (6)C28A—C29A—C30A—C31A0.6 (7)
C27—C26—C31—C32176.4 (4)C29A—C30A—C31A—C26A1.5 (7)
C27—C28—C29—C303.4 (7)C29A—C30A—C31A—C32A178.9 (4)
C28—C29—C30—C311.8 (7)C30A—C31A—C32A—C33A179.5 (4)
C29—C30—C31—C261.0 (7)C31A—C26A—C27A—C28A0.7 (6)
C29—C30—C31—C32177.6 (5)C31A—C32A—C33A—C34A1.7 (7)
C30—C31—C32—C33179.0 (4)C32A—C33A—C34A—N3A177.2 (4)
C31—C26—C27—C280.7 (6)C32A—C33A—C34A—C25A0.1 (6)
C31—C32—C33—C341.5 (7)C34A—N3A—C35A—C36A75.9 (5)
C32—C33—C34—N3176.0 (4)C34A—C25A—C26A—C27A176.5 (4)
C32—C33—C34—C251.1 (7)C34A—C25A—C26A—C31A3.6 (6)
C34—N3—C35—C3677.6 (5)C35A—N3A—C34A—C25A174.4 (4)
C34—C25—C26—C27175.9 (4)C35A—N3A—C34A—C33A8.3 (6)
C34—C25—C26—C313.2 (6)C35A—C36A—C37A—C38A178.0 (4)
C35—N3—C34—C25171.6 (4)C36A—N4A—C48A—C39A10.2 (6)
C35—N3—C34—C3313.5 (6)C36A—N4A—C48A—C47A169.0 (4)
C35—C36—C37—C38179.6 (4)C36A—C37A—C38A—C39A4.7 (7)
C36—N4—C48—C3911.2 (6)C37A—C38A—C39A—C40A179.1 (5)
C36—N4—C48—C47166.5 (4)C37A—C38A—C39A—C48A1.4 (7)
C36—C37—C38—C394.7 (7)C38A—C39A—C40A—C41A179.4 (5)
C37—C38—C39—C40179.4 (5)C38A—C39A—C48A—N4A6.0 (7)
C37—C38—C39—C481.3 (7)C38A—C39A—C48A—C47A173.2 (4)
C38—C39—C40—C41178.6 (5)C39A—C40A—C41A—C42A3.6 (8)
C38—C39—C48—N46.7 (6)C40A—C39A—C48A—N4A173.5 (4)
C38—C39—C48—C47171.0 (4)C40A—C39A—C48A—C47A7.3 (7)
C39—C40—C41—C424.2 (7)C40A—C41A—C42A—C43A176.9 (5)
C40—C39—C48—N4172.7 (4)C40A—C41A—C42A—C47A2.2 (8)
C40—C39—C48—C479.6 (6)C41A—C42A—C43A—C44A175.9 (5)
C40—C41—C42—C43174.4 (5)C41A—C42A—C47A—C46A173.3 (5)
C40—C41—C42—C472.8 (7)C41A—C42A—C47A—C48A3.9 (7)
C41—C42—C43—C44174.7 (5)C42A—C43A—C44A—C45A0.5 (9)
C41—C42—C47—C46171.6 (4)C42A—C47A—C48A—N4A172.3 (4)
C41—C42—C47—C484.7 (7)C42A—C47A—C48A—C39A8.5 (6)
C42—C43—C44—C450.9 (8)C43A—C42A—C47A—C46A5.8 (7)
C42—C47—C48—N4171.4 (4)C43A—C42A—C47A—C48A177.0 (4)
C42—C47—C48—C3910.8 (6)C43A—C44A—C45A—C46A1.6 (8)
C43—C42—C47—C465.7 (7)C44A—C45A—C46A—C47A1.2 (8)
C43—C42—C47—C48178.1 (4)C45A—C46A—C47A—C42A4.8 (7)
C43—C44—C45—C461.1 (8)C45A—C46A—C47A—C48A178.2 (4)
C44—C45—C46—C472.1 (7)C46A—C47A—C48A—N4A10.7 (7)
C45—C46—C47—C425.5 (7)C46A—C47A—C48A—C39A168.5 (4)
C45—C46—C47—C48178.4 (4)C47A—C42A—C43A—C44A3.2 (8)
C46—C47—C48—N412.4 (7)C48A—N4A—C36A—C35A170.6 (4)
C46—C47—C48—C39165.3 (4)C48A—N4A—C36A—C37A6.9 (6)
C47—C42—C43—C442.5 (8)C48A—C39A—C40A—C41A1.1 (7)
C48—N4—C36—C35171.7 (4)C49A—S1A—O1A—Zn1A91.3 (5)
C48—N4—C36—C377.7 (7)O7—S3—C51—F763.0 (5)
C48—C39—C40—C412.1 (7)O7—S3—C51—F857.8 (5)
C49—S1—O1—Zn1167.8 (3)O7—S3—C51—F9176.6 (4)
Zn1A—N1A—C1A—C2A26.9 (6)O8—S3—C51—F7178.3 (5)
Zn1A—N1A—C1A—C10A151.3 (4)O8—S3—C51—F860.9 (5)
Zn1A—N1A—C13A—C12A164.9 (4)O8—S3—C51—F957.9 (5)
Zn1A—N1A—C13A—C14A13.1 (5)O9—S3—C51—F758.7 (5)
Zn1A—N2A—C14A—C13A7.1 (5)O9—S3—C51—F8179.5 (5)
Zn1A—N2A—C15A—C16A118.4 (4)O9—S3—C51—F961.6 (5)
Zn1A—N2A—C15A—C24A55.0 (5)O4—S2—C50—F461.3 (5)
Zn1A—N3A—C34A—C25A73.7 (4)O4—S2—C50—F558.4 (5)
Zn1A—N3A—C34A—C33A103.6 (4)O4—S2—C50—F6179.6 (4)
Zn1A—N3A—C35A—C36A39.2 (4)O5—S2—C50—F4178.7 (4)
Zn1A—N4A—C36A—C35A34.1 (4)O5—S2—C50—F561.7 (5)
Zn1A—N4A—C36A—C37A148.4 (4)O5—S2—C50—F660.3 (5)
Zn1A—N4A—C48A—C39A139.9 (4)O6—S2—C50—F459.0 (5)
Zn1A—N4A—C48A—C47A40.9 (5)O6—S2—C50—F5178.6 (4)
O2B—S1B—O1B—Zn1A6.0 (16)O6—S2—C50—F659.3 (5)
 

Acknowledgements

The authors would like to thank Kansas State University for instrument support.

Funding information

Funding for this research was provided by: Creighton University; Cambridge Isotope Laboratories, Inc.; National Science Foundation, Division of Chemistry (award No. CHE-0349258).

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