Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270113021148/yp3040sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270113021148/yp3040compound1sup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270113021148/yp3040compound2sup3.hkl |
CCDC references: 964754; 964755
Crystal data, data collection and structure refinement details are summarized in Table 1.
The synthesis of (1) was achieved following the procedure described for Li[bdmpzdta] (Otero et al., 2002). This procedure is almost identical to the procedures reported by others previously (Bassanetti et al., 2010; Spiropulos et al., 2011). Bis(3,5-di-tert-butylpyrazol-1-yl)methane (bdtbpzm) was treated with an equimolar amount of n-butyllithium at low temperature in tetrahydrofuran. Upon warming, an excess of carbon disulfide was added inducing an instant colour change to deep red (Fig. 6). Upon standing overnight the product separated from the solution as the red lithium salt [Li(bdtbpzdta)(THF)].THF. Precipitation was completed by partial removal of the solvent and cooling to 243 K. No attempts were made to obtain the solvent free product. The 1H NMR spectrum displays two multiplet signals for the two tetrahydrofuran molecules (1.76 and 3.60 p.p.m.). The appropriate signals are also present in the 13C NMR spectrum (25.1 and 67.0 p.p.m.). Signals at 1.24 and 1.76 p.p.m. (1H) and at 30.4, 30.6, 31.4, and 31.6 p.p.m. (13C) are assigned to the tert-butyl substituents. In the IR spectrum, the C—S vibrations occur at ν(CS2)asym = 1085 cm-1 and ν(CS2)sym = 801 cm-1. In the MS, the [Li(bdtbpzdta)]+ ion is detected at m/z = 455. The spectroscopic data agrees well with that reported in the literature (Bassanetti et al., 2010; Spiropulos et al., 2011).
The zinc-dependent metalloprotein peptide deformylase in eubacteria is essential for bacterial survival. The active site of this class of enzymes features a tetrahedral N,N,S-coordination of the coenzyme zinc by two histidine and one cysteine residues (Fig. 1) (Dirk et al., 2008). These enzymes catalyse the hydrolysis of an N-terminal formyl group of methionine (Fig. 2), which is essential for the bacterial protein synthesis, growth, and survival (Goldberg et al., 2005). The high activity of anti-PDF drugs on bacterial PDF and the low effect on mammal and vegetal PDFs, make inhibitors for PDFs interesting for potential anti-bacterial drugs. Derivatives of hydroxamic acids are widely used as model inhibitors for these enzymes (Guay, 2007). Several model complexes have been established to mimic the active site of zinc PDFs, such as Zinc Tp or bis(pyrazol-1-yl)acetato complexes (Ruf et al., 1996; Hammes et al., 2003). Furthermore, heteroscorpionate N,N,S ligands were employed, such as (2-methylethanethiol-bis(3,5-dimethylpyrazol-1-yl)methane, because these due to higher similarity appear more suitable to model the active site of the zinc PDFs. Complexes thereof include acetohydroxamato derived inhibitors or acetate as ligands as well as halogenido donors (Figure 3) (Hammes et al., 2003; Galardon et al., 2007; Hammes & Carrano, 2000, 2001). So far, only little research has been done on bis(pyrazol-1-yl)dithioacetato ligands, although some complexes of Cu, Ru as well as of the early transition metals titanium, hafnium, zirconium, scandium, and yttrium have been described (Ortiz et al., 2005; Otero et al., 2002, 2004a, 2004b, 2005). Under similar conditions, the bulkier lithium bis(3,5-diphenylpyrazol-1-yl)dithioacetate Li[bdphpzdt] was isolated as a water and tetrahydrofuran adduct [Li(bdphpzdta)(THF)(H2O)], as well as [Li(bdphpza)(THF)(H2O)] [bdphpza = bis(3,5-diphenylpyrazol-1-yl)acetate]. Although structural data is only available for [Li(bdphpzdta)(THF)(H2O)] (Figure 5), the lithium ion in all three salts is most likely coordinated tetrahedrally by the two pyrazolyl moieties and the tetrahydrofuran/water molecules (Otero et al., 2002). In case of the bis(3,5-di-tert-butylpyrazol-1-yl)dithioacetate (bdtbpzdta) the molecular structure gained by X-ray structure determination revealed formation of a trinuclear complex [Li(bdtbpzdta)]3.2.25THF (Bassanetti et al., 2010). Nevertheless, in contrast to this N2S2 coordination mode also an ?3-N2S coordination was recently reported for [Zn(bdtbpzdta)Br] (Spiropulos et al., 2011).
Crystals suitable for single-crystal X-ray structure analysis were obtained from the mother liquor. A presentation of the molecular structure is given in Fig. 7. Selected bond lengths and angles are summarized in Table 1. The substance crystallises in the space group P21/c with Z = 4. The final structural model shows rotational disorder for the two tert-butyl groups of the pyrazole ring containing atom N1 with a ratio of 51:49 and 81:19, respectively. Fig. 7 depicts the fragment with the higher occupancy. Also a non coordinated THF molecule is disordered and was refined on two different positions with an occupancy ratio of 66:33. SIMU restraints (SIMU 0.01 0.02) have been applied for each of the disordered tert-butyl groups and the disordered THF as well, resulting in 180 restraints. An additional 30 restraints were applied by linking the disordered noncoordinated THF to the coordinated THF (via SAME O1 > C28) to ensure chemical reasonable distances and angles in the disordered THF.
The lithium ion is coordinated by the bdtbpzdta ligand and the tetrahydrofuran molecule in a tetrahedral geometry. Thus, the bdtbpzdta ligand features an N,N',S-coordination, whereas the aforementioned ligand bdphpzdta coordinates to the Li atom in [Li(bdphpzdta)(THF)(H2O)] in a N,N'-mode,. The bond lengths involving sulfur are 1.675 (3) (C—S), 1.660 (2) (C═S), and 2.492 (4) Å (Li—S). In contrast to these findings, the CS2 group in [Li(bdphpzdta)(THF)(H2O)] remains nonbonded, and the C—S bond lengths are slightly shorter [1.663 (7) and 1.655 (7) Å]. The Li—O distance is 1.957 (3)Å. The Li—N distances are 2.085 (4) and 2.060 (5)Å. These bond lengths are comparable to the values of [Li(bdphpzdta)(THF)(H2O)] [Li—N = 2.07 (1) and 2.06 (1)Å and Li—O = 1.94 (1)Å; Otero et al., 2002].
For the syntheses of [Zn(bdtbpzdta)Cl], (2), [Li(bdtbpzdta)(THF)].THF, (1), was treated with a slight excess of anhydrous zinc chloride at room temperature. In order to separate any unreacted zinc chloride, the crude product was dried and re-dissolved in dichloromethane, the salts were filtered off, and the product was precipitated with pentane (Fig. 8).
Compared to the starting lithium compound the 1H NMR spectra of the zinc complex 2 shows considerable down-field shifts of the resonances. Thus, the signals arising from the tert-butyl groups are shifted from 1.11 and 1.24 p.p.m. to 1.44 and 1.49 p.p.m. (CD2Cl2) and to 1.46 and 1.52 p.p.m. (CDCl3), respectively. In the 13C NMR spectrum, coordination of the dithiocarboxylate moiety to zinc caused an up-field shift of the CS2- carbon signal from 248.4 to 238.3 p.p.m. (CDCl3). In the IR spectra, the dithiocarboxylate resonances were assigned to bands at νasym = 1084cm-1 (KBr) and 1082cm-1 (CH2Cl2).
Red crystals suitable for an X-ray single-crystal structure determination could be obtained from a dichloromethane solution. The molecular structure is shown in Fig. 9. Relevant bond lengths and angles are given in Table 3. The substance crystallizes in the space group P21/n with Z = 4. The [Zn(bdtbpzdta)Cl] molecule features the expected tetrahedral coordination geometry. The two pyrazole donors are tilted to each other by 41.2°. The dithioacetate group displays an almost coplanar or linear coordination with respect to the zinc dithioacetate plane compared to the lithium compound [Li(bdtbpzdta)(THF)], (1), and the complexes [Zn(bdtbpza)Cl], [Zn(bdmpzEtMe2S)Cl], [Zn(bdmpzEtMe2S)(PhN(O)C(O)H)], and [Zn(b3campzEtMe2S)Cl], where the O- or S-donor groups are tilted (Galardon et al., 2007; Hammes & Carrano, 2000; Beck et al., 2001; Godau et al., 2009). The Zn—S bond length is 2.3335 (5)Å, and is thus comparable to that of [Zn(HBpz23tBuim2S)Cl] [2.323 (1) Å; Benkmil et al., 2004] and [Zn(bdtbpzdta)Br] [2.334 (2) Å; Spiropulos et al., 2011]. The two Zn—N distances differ by 0.08 Å [2.0490 (13) and 2.1338 (13) Å], which contrasts to the data of complexes known from the literature, where Zn–pyrazole bonds are of almost identical in length (2.1 Å). The Zn—Cl bond length is 2.1832 (5) Å. The valence angles at the zinc centre differ only marginally from those reported for related complexes, apart from the rather small N—Zn—N angle of 86.49 (5)° which again agrees well with that of [Zn(bdtbpzdta)Br] [86.8 (3)°; Spiropulos et al., 2011].
In summary, we observed an coordination mode of the bis(di-tert-butylpyrazol-1-yl)dithioacetate ligand in the molecular structures of [Li(bdtbpzdta)THF].THF, (1), and [Zn(bdtbpzdta)Cl], (2). This coordination mode resembles nicely the metal ion coordination reported for the peptide deformylases (PDFs) and makes this ligand a promising candidate for more advanced structural models regarding these enzymes.
To a tetrahydrofuran solution (200 ml) of bdtbpzm (14.85 g, 40.1 mmol), one equivalent of n-BuLi (25.1 ml, 40.1 mmol, 1.6 M in n-hexane) was added at 193 K. After warming to 233 K within 3 h, 1.5 equivalents of CS2 (3.6 ml, 40.1 mmol) were added. The turbid solution instantly turned deep red and was stirred for an additional 18h reaching ambient temperature. Half of the solvent was removed in vacuo. After storing the solution in a refrigerator at 243 K overnight, the light-red product was filtered off and washed twice with a small amount of THF (2 × 10 ml) yielding 16.7 g (27.9 mmol, 69.6%) as a first crop of [Li(bdtbpzdta)(THF)].THF, (1).
1H NMR (300 K, 300 MHz, DMSO-d6): δ 1.11 (s, 18H, t-Bu), 1.24 (s, 18H, t-Bu), 1.76 (m, 8H, THF), 3.60 (m, 8H, THF), 5.81 (s, 2H, CH), 7.48 (s, 1H, CH); 13C{1H} NMR (300 K, 75.5 MHz, DMSO-d6): δ 25.1 (THF), 30.4 (s, Me), 30.6 (s, Me), 31.4 (s, Ct-Bu), 31.6 (s, Ct-Bu), 67.0 (THF), 99.8 (s, CH), 150.9 (s, Cpz), 155.8 (s, Cpz), 245.4 (s, CS2-); 13C{1H} NMR (300 K, 75.5 MHz, CDCl3): δ 25.5 (THF), 30.3 (s, Me), 30.9 (s, Me), 31.8 (s, Ct-Bu), 31.9 (s, Ct-Bu), 67.8 (THF), 83.7 (s, CH), 101.7 (s, Cpz), 153.5 (s, Cpz), 161.1 (s, Cpz), 248.4 (s, CS2-). FD+ MS: m/z (%) 455 (100) [Li(bdtbpzdta)+H]+. IR (KBr): ν (cm-1) = 2965 (s), 2872 (m), 1653 (w), 1542 (m), 1462 (m), 1443 (m), 1364 (m), 1317 (m), 1253 (m), 1224 (m), 1085 (s), 1057 (m), 1036 (m), 1009 (m), 878 (m), 853 (w), 801 (m), 744 (m), 622 (w), 445 (w). IR (CH2Cl2): ν? (cm-1) = 2971 (s), 2909 (w), 2874 (w), 1543 (w), 1464 (w), 1364 (m), 1226 (w), 1083 (m),1063m, 1037 (m), 1037 (w), 1006 (w). CHN analysis calculated for C32H55LiN4O2S2, (1): C 64.18, H 9.26, N 9.36, S 10.71%; found: C 63.86, H 9.21, N 9.41, S 10.79%.
To an acetonitrile solution (100 ml) of anhydrous ZnCl2 (590 mg, 4.33 mmol) [Li(bdtbpzdta)(THF)].THF, (1) (2.59 g, 4.33 mmol), was added and stirred overnight. All volatiles were removed in vacuo and dichloromethane (50 ml) was added. The solution was filtered through celite and the solvent was removed in vacuo to yield 1.91 g (3.47 mmol, 80.1%) of [Zn(bdtbpzdta)Cl], (2), as a light-red solid (m.p. ~452 K (decomposition). 1H NMR (298 K, 300 MHz, CD2Cl2): δ 1.44 (s, 18H, t-Bu), 1.49 (s, 18H, t-Bu), 6.24 (s, 2H, pz), 8.07 (s, 1H, CH). 1H NMR (298 K, 300 MHz, CDCl3): δ 1.46 (s, 18H, t-Bu), 1.52 (s, 18H, t-Bu'), 6.20 (s, 2H, pz), 8.09 (s, 1H, CH). 13C{1H} NMR (298 K, 75.5 MHz, CD2Cl2): δ 30.4 (s, Me), 31.4 (s, Me), 32.8 (s, Ct-Bu), 33.2 (s, Ct-Bu), 81.6 (s, CH), 105.0 (s, Cpz), 157.3 (s, Cpz), 165.6 (s, Cpz), 239.0 (s, CS2-); 13C{1H} NMR (298 K, 75.5 MHz, CDCl3): δ 30.3 (s, Me), 31.2 (s, Me), 32.5 (s, Ct-Bu), 32.8 (s, Ct-Bu), 81.1 (s, CH), 104.3 (s, Cpz), 156.6 (s, Cpz), 165.1 (s, Cpz), 238.3 (s, CS2-). FD+ MS: m/z (%) 549 (100) [MH]+. IR (KBr): ν? (cm-1) = 2965 (s), 2872 (w), 1543 (m), 1533 (m), 1369 (m), 1339 (w), 1309 (w), 1253 (m), 1223 (m), 1136 (w), 1084 (s), 1058 (m), 1025 (w), 1010 (w), 879 (w), 827 (m), 790 (m), 720 (m), 690 (w), 625 (w). IR (CH2Cl2): ν?(cm–1) = 1543 (m), 1466 (w), 1439 (w), 1368 (m), 1249 (m), 1219 (s), 1082 (s), 1051 (m), 1026 (w). CHN analysis calculated for C24H39ClN4S2Zn: C 52.55, H 7.17, N 10.21, S 11.69%; found: C 52.42, H 7.39, N 10.27, S 11.45%.
Data collection: APEX2 (Bruker, 2008) for compound1; COLLECT (Hooft, 1999) for compound2. Cell refinement: SAINT (Bruker, 2008) for compound1; EVALCCD (Duisenberg et al., 2003) for compound2. Data reduction: SAINT (Bruker, 2008) for compound1; EVALCCD (Duisenberg et al., 2003) for compound2. Program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) for compound1; SHELXS86 (Sheldrick, 2008) for compound2. For both compounds, program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).
(a) Zinc-dependent peptide deformylase (PDF) and (b) the
N,N',S-coordination motif of the active site (PDB: 3CPM)
(Dirk et al., 2008). The deformylation reaction of PDF in the peptide biosynthesis. Zinc complexes bearing bispyrazolyl-based thiolate and thioether ligands. The synthesis of [Li(bdmpzdta)] according to the literature. Conditions: (i) n-BuLi; (ii) CS2. The molecular structure of [Li(bdphpzdta)(H2O)(THF)]. Cocrystallised solvent has been omitted for clarity (Otero et al., 2002). The synthesis of [Li(bdtbpzdta)(THF)].THF, (1). Conditions: (i) n-BuLi, 353 K; (ii) CS2. The molecular structure of [Li(bdtbpzdta)(THF)].THF, (1) (main orientation of the disordered t-Bu group depicted). Displacement ellipsoids are drawn at the 50% probability level. H atoms and cocrystallised solvent have been omitted for clarity. The synthesis of [Zn(bdtbpzdta)Cl], (2). Conditions: (i) ZnCl2; (ii) CH2Cl2/pentane The molecular structure of [Zn(bdtbpzdta)Cl], (2), Displacement ellipsoids are drawn at the 50% probability level. H atoms have been omitted for clarity. |
[Li(C24H39N4S2)(C4H8O)]·C4H8O | F(000) = 1304 |
Mr = 598.86 | Dx = 1.132 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4077 reflections |
a = 12.4026 (3) Å | θ = 2.5–23.8° |
b = 16.3932 (4) Å | µ = 0.18 mm−1 |
c = 17.8867 (4) Å | T = 220 K |
β = 105.013 (2)° | Block, orange |
V = 3512.56 (14) Å3 | 0.34 × 0.3 × 0.2 mm |
Z = 4 |
Bruker SMART APEXII diffractometer | 7066 independent reflections |
Graphite monochromator | 4549 reflections with I > 2σ(I) |
Detector resolution: 83.33 pixels mm-1 | Rint = 0.050 |
ϕ and ω scans | θmax = 26.4°, θmin = 2.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −15→15 |
Tmin = 0.687, Tmax = 0.746 | k = −20→20 |
25289 measured reflections | l = −22→22 |
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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.155 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0709P)2 + 0.7204P] where P = (Fo2 + 2Fc2)/3 |
7066 reflections | (Δ/σ)max = 0.037 |
490 parameters | Δρmax = 0.42 e Å−3 |
210 restraints | Δρmin = −0.29 e Å−3 |
[Li(C24H39N4S2)(C4H8O)]·C4H8O | V = 3512.56 (14) Å3 |
Mr = 598.86 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.4026 (3) Å | µ = 0.18 mm−1 |
b = 16.3932 (4) Å | T = 220 K |
c = 17.8867 (4) Å | 0.34 × 0.3 × 0.2 mm |
β = 105.013 (2)° |
Bruker SMART APEXII diffractometer | 7066 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | 4549 reflections with I > 2σ(I) |
Tmin = 0.687, Tmax = 0.746 | Rint = 0.050 |
25289 measured reflections |
R[F2 > 2σ(F2)] = 0.054 | 210 restraints |
wR(F2) = 0.155 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.42 e Å−3 |
7066 reflections | Δρmin = −0.29 e Å−3 |
490 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The final structural model shows rotational disorder for the two tert-butyl groups of the pyrazolyl ring containing N1 with a ratio of 51:49 and 81:19, respectively. Figure 7 depicts the fragment with the higher occupancy. Also a non coordinated THF molecule is disordered and was refined on two different positions with an occupancy ratio of 66:33. SIMU restraints (SIMU 0.01 0.02 C5 > C7A; SIMU 0.01 0.02 C9 > C11A; SIMU 0.01 0.02 O2 > C32A) have been applied for each of the disordered tert-butyl groups and the disordered THF as well, resulting in 180 restraints. Additional 30 restraints were applied by linking the disordered THF to the coordinated THF (via SAME O1 > C28) to ensure chemical reasonable distances and angles in the disordered THF. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
S1 | 0.50049 (5) | 0.82629 (4) | 0.04498 (4) | 0.0456 (2) | |
S2 | 0.50893 (6) | 0.65679 (5) | 0.10867 (4) | 0.0542 (2) | |
N1 | 0.70873 (15) | 0.81874 (11) | −0.04239 (10) | 0.0334 (4) | |
N2 | 0.64554 (15) | 0.74906 (11) | −0.05018 (10) | 0.0328 (4) | |
N3 | 0.74992 (15) | 0.70770 (11) | 0.07637 (10) | 0.0320 (4) | |
N4 | 0.77524 (15) | 0.77819 (12) | 0.11917 (10) | 0.0343 (4) | |
C1 | 0.69882 (18) | 0.84496 (14) | −0.11427 (13) | 0.0351 (5) | |
C2 | 0.6279 (2) | 0.79386 (16) | −0.16745 (13) | 0.0421 (6) | |
H2A | 0.6076 | 0.7998 | −0.2216 | 0.051* | |
C3 | 0.59315 (19) | 0.73333 (15) | −0.12613 (13) | 0.0377 (6) | |
C4 | 0.7610 (2) | 0.91937 (15) | −0.12973 (13) | 0.0408 (6) | |
C5 | 0.8587 (8) | 0.8871 (4) | −0.1622 (7) | 0.093 (3) | 0.513 (7) |
H5A | 0.8286 | 0.8539 | −0.2077 | 0.139* | 0.513 (7) |
H5B | 0.909 | 0.8544 | −0.123 | 0.139* | 0.513 (7) |
H5C | 0.8992 | 0.9329 | −0.176 | 0.139* | 0.513 (7) |
C6 | 0.6905 (7) | 0.9699 (5) | −0.1922 (6) | 0.091 (3) | 0.513 (7) |
H6A | 0.6232 | 0.9859 | −0.1779 | 0.137* | 0.513 (7) |
H6B | 0.6705 | 0.9386 | −0.2398 | 0.137* | 0.513 (7) |
H6C | 0.7316 | 1.0182 | −0.1997 | 0.137* | 0.513 (7) |
C7 | 0.8116 (12) | 0.9678 (6) | −0.0588 (5) | 0.107 (4) | 0.513 (7) |
H7A | 0.7529 | 0.9938 | −0.0406 | 0.161* | 0.513 (7) |
H7B | 0.8605 | 1.0091 | −0.0708 | 0.161* | 0.513 (7) |
H7C | 0.8542 | 0.9319 | −0.0188 | 0.161* | 0.513 (7) |
C5A | 0.7753 (10) | 0.9194 (6) | −0.2101 (5) | 0.096 (3) | 0.487 (7) |
H5AA | 0.7029 | 0.9149 | −0.2469 | 0.144* | 0.487 (7) |
H5AB | 0.8215 | 0.8734 | −0.2164 | 0.144* | 0.487 (7) |
H5AC | 0.8111 | 0.9697 | −0.2191 | 0.144* | 0.487 (7) |
C6A | 0.6860 (6) | 0.9945 (4) | −0.1231 (6) | 0.081 (3) | 0.487 (7) |
H6AA | 0.6617 | 0.9902 | −0.0758 | 0.121* | 0.487 (7) |
H6AB | 0.6213 | 0.9955 | −0.1673 | 0.121* | 0.487 (7) |
H6AC | 0.7285 | 1.0444 | −0.1219 | 0.121* | 0.487 (7) |
C7A | 0.8691 (6) | 0.9301 (6) | −0.0697 (6) | 0.074 (3) | 0.487 (7) |
H7AA | 0.8563 | 0.9262 | −0.0186 | 0.112* | 0.487 (7) |
H7AB | 0.9002 | 0.9832 | −0.0759 | 0.112* | 0.487 (7) |
H7AC | 0.921 | 0.8879 | −0.0758 | 0.112* | 0.487 (7) |
C8 | 0.5074 (2) | 0.66674 (16) | −0.15768 (14) | 0.0472 (7) | |
C9 | 0.4641 (7) | 0.6814 (5) | −0.2452 (4) | 0.088 (3) | 0.808 (13) |
H9A | 0.5252 | 0.6756 | −0.2694 | 0.132* | 0.808 (13) |
H9B | 0.4334 | 0.736 | −0.2543 | 0.132* | 0.808 (13) |
H9C | 0.4065 | 0.6418 | −0.2671 | 0.132* | 0.808 (13) |
C10 | 0.5547 (6) | 0.5816 (3) | −0.1453 (4) | 0.0743 (18) | 0.808 (13) |
H10A | 0.6199 | 0.5779 | −0.1655 | 0.111* | 0.808 (13) |
H10B | 0.4989 | 0.5428 | −0.172 | 0.111* | 0.808 (13) |
H10C | 0.5758 | 0.5693 | −0.0903 | 0.111* | 0.808 (13) |
C11 | 0.4073 (5) | 0.6752 (4) | −0.1228 (4) | 0.0714 (17) | 0.808 (13) |
H11A | 0.3833 | 0.7317 | −0.1257 | 0.107* | 0.808 (13) |
H11B | 0.4288 | 0.6579 | −0.0691 | 0.107* | 0.808 (13) |
H11C | 0.3465 | 0.6413 | −0.1515 | 0.107* | 0.808 (13) |
C9A | 0.512 (4) | 0.644 (2) | −0.2394 (16) | 0.095 (8) | 0.192 (13) |
H9A1 | 0.4507 | 0.6074 | −0.262 | 0.143* | 0.192 (13) |
H9A2 | 0.5822 | 0.6176 | −0.2377 | 0.143* | 0.192 (13) |
H9A3 | 0.5049 | 0.6932 | −0.2707 | 0.143* | 0.192 (13) |
C10A | 0.518 (2) | 0.5825 (13) | −0.1102 (17) | 0.068 (6) | 0.192 (13) |
H10D | 0.4814 | 0.5881 | −0.0686 | 0.102* | 0.192 (13) |
H10E | 0.5961 | 0.5695 | −0.0886 | 0.102* | 0.192 (13) |
H10F | 0.4825 | 0.539 | −0.1447 | 0.102* | 0.192 (13) |
C11A | 0.397 (2) | 0.6983 (19) | −0.163 (2) | 0.079 (7) | 0.192 (13) |
H11D | 0.3975 | 0.7281 | −0.1159 | 0.118* | 0.192 (13) |
H11E | 0.3446 | 0.6534 | −0.1689 | 0.118* | 0.192 (13) |
H11F | 0.3751 | 0.7345 | −0.207 | 0.118* | 0.192 (13) |
C12 | 0.64205 (18) | 0.70426 (15) | 0.01973 (12) | 0.0333 (5) | |
H12A | 0.6282 | 0.6463 | 0.0046 | 0.04* | |
C13 | 0.54890 (18) | 0.73052 (15) | 0.05815 (13) | 0.0366 (6) | |
C14 | 0.83005 (19) | 0.64977 (15) | 0.09937 (13) | 0.0359 (5) | |
C15 | 0.90923 (19) | 0.68445 (16) | 0.15871 (14) | 0.0412 (6) | |
H15A | 0.9756 | 0.6597 | 0.1871 | 0.049* | |
C16 | 0.87333 (18) | 0.76334 (15) | 0.16942 (12) | 0.0364 (6) | |
C17 | 0.8319 (2) | 0.56637 (16) | 0.06327 (14) | 0.0446 (6) | |
C18 | 0.8322 (2) | 0.57615 (18) | −0.02235 (15) | 0.0520 (7) | |
H18A | 0.9002 | 0.6034 | −0.0256 | 0.078* | |
H18B | 0.7682 | 0.6084 | −0.049 | 0.078* | |
H18C | 0.8283 | 0.5228 | −0.0464 | 0.078* | |
C19 | 0.7354 (3) | 0.51225 (17) | 0.07224 (17) | 0.0583 (8) | |
H19A | 0.7387 | 0.5063 | 0.1267 | 0.087* | |
H19B | 0.7414 | 0.459 | 0.05 | 0.087* | |
H19C | 0.665 | 0.5372 | 0.0457 | 0.087* | |
C20 | 0.9405 (3) | 0.52413 (19) | 0.10463 (18) | 0.0653 (8) | |
H20A | 0.9432 | 0.5176 | 0.159 | 0.098* | |
H20B | 1.0034 | 0.557 | 0.0997 | 0.098* | |
H20C | 0.9441 | 0.471 | 0.0816 | 0.098* | |
C21 | 0.9301 (2) | 0.82853 (17) | 0.22574 (14) | 0.0442 (6) | |
C22 | 1.0347 (2) | 0.7935 (2) | 0.28147 (17) | 0.0706 (9) | |
H22A | 1.0142 | 0.7477 | 0.3092 | 0.106* | |
H22B | 1.07 | 0.8353 | 0.3181 | 0.106* | |
H22C | 1.0864 | 0.7753 | 0.2524 | 0.106* | |
C23 | 0.8492 (2) | 0.8597 (2) | 0.27062 (17) | 0.0606 (8) | |
H23A | 0.8284 | 0.8152 | 0.2998 | 0.091* | |
H23B | 0.7829 | 0.8813 | 0.2347 | 0.091* | |
H23C | 0.8848 | 0.9024 | 0.3059 | 0.091* | |
C24 | 0.9652 (2) | 0.89896 (19) | 0.18110 (17) | 0.0610 (8) | |
H24A | 0.8995 | 0.923 | 0.1465 | 0.091* | |
H24B | 1.0146 | 0.8786 | 0.1512 | 0.091* | |
H24C | 1.0039 | 0.94 | 0.2173 | 0.091* | |
Li1 | 0.6941 (3) | 0.8768 (3) | 0.0583 (2) | 0.0407 (9) | |
O1 | 0.69211 (15) | 0.98799 (11) | 0.09766 (11) | 0.0536 (5) | |
C25 | 0.6046 (3) | 1.00941 (19) | 0.1326 (2) | 0.0699 (9) | |
H25A | 0.5801 | 0.9613 | 0.1564 | 0.084* | |
H25B | 0.5405 | 1.0314 | 0.0936 | 0.084* | |
C26 | 0.6508 (4) | 1.0724 (3) | 0.1928 (3) | 0.1142 (16) | |
H26A | 0.665 | 1.0492 | 0.2449 | 0.137* | |
H26B | 0.5992 | 1.1184 | 0.1886 | 0.137* | |
C27 | 0.7588 (3) | 1.0993 (2) | 0.1756 (2) | 0.0983 (13) | |
H27A | 0.7624 | 1.1589 | 0.1726 | 0.118* | |
H27B | 0.8234 | 1.0799 | 0.2157 | 0.118* | |
C28 | 0.7557 (3) | 1.06179 (18) | 0.0999 (2) | 0.0676 (9) | |
H28A | 0.7195 | 1.0983 | 0.0574 | 0.081* | |
H28B | 0.8314 | 1.0495 | 0.0958 | 0.081* | |
O2 | 0.1078 (4) | 0.8440 (3) | −0.4725 (3) | 0.1200 (17) | 0.665 (5) |
C29 | 0.2012 (7) | 0.8312 (5) | −0.4191 (6) | 0.117 (2) | 0.665 (5) |
H29A | 0.1982 | 0.8578 | −0.3706 | 0.141* | 0.665 (5) |
H29B | 0.2645 | 0.8537 | −0.4357 | 0.141* | 0.665 (5) |
C30 | 0.2151 (8) | 0.7404 (5) | −0.4072 (5) | 0.115 (2) | 0.665 (5) |
H30A | 0.1874 | 0.7212 | −0.3637 | 0.138* | 0.665 (5) |
H30B | 0.2926 | 0.7229 | −0.4002 | 0.138* | 0.665 (5) |
C31 | 0.1351 (8) | 0.7118 (6) | −0.4905 (6) | 0.127 (2) | 0.665 (5) |
H31A | 0.1723 | 0.7182 | −0.5322 | 0.152* | 0.665 (5) |
H31B | 0.1101 | 0.6552 | −0.4891 | 0.152* | 0.665 (5) |
C32 | 0.0458 (7) | 0.7678 (5) | −0.4978 (5) | 0.122 (2) | 0.665 (5) |
H32A | −0.0021 | 0.7532 | −0.4641 | 0.147* | 0.665 (5) |
H32B | 0.0004 | 0.7716 | −0.5514 | 0.147* | 0.665 (5) |
O2A | 0.1108 (10) | 0.6896 (7) | −0.4520 (8) | 0.134 (3) | 0.335 (5) |
C29A | 0.2054 (16) | 0.7054 (10) | −0.3954 (11) | 0.125 (4) | 0.335 (5) |
H29C | 0.2716 | 0.6853 | −0.4099 | 0.15* | 0.335 (5) |
H29D | 0.2022 | 0.6801 | −0.3463 | 0.15* | 0.335 (5) |
C30A | 0.2070 (15) | 0.7973 (10) | −0.3891 (9) | 0.110 (3) | 0.335 (5) |
H30C | 0.2786 | 0.8193 | −0.3589 | 0.132* | 0.335 (5) |
H30D | 0.1451 | 0.8196 | −0.3709 | 0.132* | 0.335 (5) |
C31A | 0.1889 (14) | 0.8052 (10) | −0.4830 (9) | 0.122 (3) | 0.335 (5) |
H31C | 0.1663 | 0.8607 | −0.5005 | 0.147* | 0.335 (5) |
H31D | 0.2581 | 0.7919 | −0.4972 | 0.147* | 0.335 (5) |
C32A | 0.1075 (17) | 0.7512 (12) | −0.5154 (9) | 0.130 (3) | 0.335 (5) |
H32C | 0.1227 | 0.7252 | −0.5609 | 0.156* | 0.335 (5) |
H32D | 0.0346 | 0.7782 | −0.5308 | 0.156* | 0.335 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0427 (3) | 0.0420 (4) | 0.0534 (4) | 0.0048 (3) | 0.0147 (3) | −0.0002 (3) |
S2 | 0.0589 (4) | 0.0542 (5) | 0.0580 (4) | 0.0000 (4) | 0.0307 (3) | 0.0137 (3) |
N1 | 0.0386 (10) | 0.0296 (11) | 0.0328 (10) | −0.0045 (9) | 0.0108 (8) | −0.0004 (8) |
N2 | 0.0418 (10) | 0.0280 (11) | 0.0286 (10) | −0.0057 (9) | 0.0089 (8) | −0.0009 (8) |
N3 | 0.0378 (10) | 0.0273 (11) | 0.0307 (10) | 0.0003 (9) | 0.0086 (8) | −0.0001 (8) |
N4 | 0.0397 (10) | 0.0319 (11) | 0.0307 (10) | 0.0008 (9) | 0.0080 (8) | −0.0010 (9) |
C1 | 0.0395 (12) | 0.0350 (14) | 0.0324 (12) | 0.0002 (11) | 0.0121 (10) | 0.0016 (11) |
C2 | 0.0567 (14) | 0.0410 (15) | 0.0281 (12) | −0.0073 (13) | 0.0100 (11) | 0.0000 (11) |
C3 | 0.0458 (13) | 0.0361 (14) | 0.0300 (12) | −0.0068 (11) | 0.0076 (10) | −0.0049 (11) |
C4 | 0.0500 (13) | 0.0368 (15) | 0.0371 (13) | −0.0082 (12) | 0.0139 (11) | 0.0052 (11) |
C5 | 0.099 (6) | 0.054 (4) | 0.155 (9) | −0.009 (4) | 0.086 (6) | 0.019 (5) |
C6 | 0.091 (5) | 0.060 (5) | 0.111 (7) | −0.008 (4) | 0.005 (5) | 0.045 (5) |
C7 | 0.180 (11) | 0.086 (8) | 0.061 (4) | −0.091 (7) | 0.040 (6) | −0.018 (5) |
C5A | 0.138 (8) | 0.096 (7) | 0.070 (5) | −0.057 (6) | 0.055 (5) | 0.000 (5) |
C6A | 0.069 (4) | 0.045 (4) | 0.129 (8) | −0.006 (3) | 0.026 (5) | 0.027 (5) |
C7A | 0.057 (4) | 0.062 (6) | 0.092 (7) | −0.028 (4) | −0.001 (4) | 0.025 (5) |
C8 | 0.0622 (16) | 0.0404 (16) | 0.0346 (14) | −0.0175 (14) | 0.0048 (12) | −0.0045 (12) |
C9 | 0.140 (6) | 0.063 (4) | 0.043 (2) | −0.054 (4) | −0.011 (3) | −0.006 (3) |
C10 | 0.097 (4) | 0.039 (2) | 0.076 (4) | −0.015 (3) | 0.002 (3) | −0.013 (3) |
C11 | 0.062 (3) | 0.078 (4) | 0.071 (4) | −0.037 (3) | 0.011 (3) | −0.014 (3) |
C9A | 0.168 (19) | 0.085 (17) | 0.043 (10) | −0.054 (14) | 0.047 (12) | −0.007 (12) |
C10A | 0.067 (11) | 0.046 (9) | 0.087 (14) | −0.029 (9) | 0.013 (9) | −0.016 (10) |
C11A | 0.057 (9) | 0.087 (15) | 0.088 (15) | −0.030 (11) | 0.012 (12) | −0.029 (13) |
C12 | 0.0405 (12) | 0.0279 (13) | 0.0310 (12) | −0.0041 (11) | 0.0087 (9) | 0.0005 (10) |
C13 | 0.0359 (11) | 0.0409 (15) | 0.0316 (12) | −0.0033 (11) | 0.0064 (9) | −0.0007 (11) |
C14 | 0.0454 (12) | 0.0348 (14) | 0.0318 (12) | 0.0075 (11) | 0.0177 (10) | 0.0075 (10) |
C15 | 0.0395 (12) | 0.0477 (16) | 0.0361 (13) | 0.0109 (12) | 0.0093 (10) | 0.0075 (12) |
C16 | 0.0372 (11) | 0.0422 (15) | 0.0297 (12) | 0.0005 (11) | 0.0083 (9) | 0.0047 (11) |
C17 | 0.0598 (15) | 0.0334 (14) | 0.0457 (14) | 0.0108 (13) | 0.0228 (12) | 0.0032 (12) |
C18 | 0.0650 (16) | 0.0486 (17) | 0.0494 (15) | 0.0071 (14) | 0.0275 (13) | −0.0029 (13) |
C19 | 0.085 (2) | 0.0341 (15) | 0.0644 (19) | 0.0000 (15) | 0.0342 (16) | 0.0019 (14) |
C20 | 0.077 (2) | 0.0505 (19) | 0.070 (2) | 0.0268 (17) | 0.0221 (16) | 0.0036 (15) |
C21 | 0.0429 (13) | 0.0508 (17) | 0.0340 (13) | −0.0039 (12) | 0.0009 (10) | −0.0022 (12) |
C22 | 0.0620 (18) | 0.079 (2) | 0.0555 (19) | −0.0047 (18) | −0.0114 (14) | −0.0011 (17) |
C23 | 0.0673 (18) | 0.066 (2) | 0.0502 (17) | −0.0158 (16) | 0.0183 (14) | −0.0203 (15) |
C24 | 0.0610 (17) | 0.062 (2) | 0.0560 (18) | −0.0190 (16) | 0.0076 (14) | −0.0020 (15) |
Li1 | 0.047 (2) | 0.035 (2) | 0.037 (2) | 0.0016 (19) | 0.0061 (17) | −0.0006 (18) |
O1 | 0.0607 (11) | 0.0361 (11) | 0.0650 (12) | −0.0033 (9) | 0.0183 (9) | −0.0049 (9) |
C25 | 0.074 (2) | 0.0506 (19) | 0.092 (2) | 0.0029 (17) | 0.0345 (18) | −0.0121 (18) |
C26 | 0.142 (4) | 0.070 (3) | 0.155 (4) | −0.035 (3) | 0.084 (3) | −0.057 (3) |
C27 | 0.103 (3) | 0.063 (2) | 0.122 (3) | −0.011 (2) | 0.017 (3) | −0.044 (2) |
C28 | 0.0710 (19) | 0.0408 (18) | 0.089 (2) | −0.0121 (16) | 0.0166 (17) | 0.0008 (17) |
O2 | 0.110 (3) | 0.076 (3) | 0.164 (4) | 0.023 (3) | 0.017 (3) | 0.032 (3) |
C29 | 0.084 (3) | 0.092 (5) | 0.172 (6) | 0.001 (4) | 0.025 (4) | 0.011 (4) |
C30 | 0.087 (3) | 0.094 (5) | 0.161 (4) | 0.010 (4) | 0.025 (3) | 0.045 (4) |
C31 | 0.123 (4) | 0.098 (5) | 0.157 (5) | 0.026 (4) | 0.033 (4) | 0.018 (4) |
C32 | 0.119 (4) | 0.111 (4) | 0.129 (5) | 0.036 (4) | 0.018 (4) | −0.007 (4) |
O2A | 0.123 (5) | 0.122 (5) | 0.156 (5) | 0.002 (4) | 0.036 (4) | 0.018 (5) |
C29A | 0.105 (6) | 0.112 (7) | 0.156 (6) | 0.005 (6) | 0.031 (5) | 0.027 (7) |
C30A | 0.081 (5) | 0.094 (7) | 0.155 (6) | −0.001 (6) | 0.030 (5) | 0.020 (6) |
C31A | 0.109 (4) | 0.094 (5) | 0.162 (5) | 0.002 (4) | 0.032 (4) | 0.039 (5) |
C32A | 0.117 (5) | 0.118 (5) | 0.149 (5) | 0.031 (5) | 0.022 (5) | 0.017 (5) |
S1—Li1 | 2.492 (4) | C14—C15 | 1.369 (3) |
N1—Li1 | 2.085 (4) | C14—C17 | 1.515 (3) |
N4—Li1 | 2.060 (5) | C15—C16 | 1.397 (3) |
Li1—O1 | 1.957 (5) | C15—H15A | 0.94 |
S1—C13 | 1.675 (3) | C16—C21 | 1.512 (3) |
S2—C13 | 1.660 (2) | C17—C20 | 1.525 (4) |
N1—C1 | 1.331 (3) | C17—C19 | 1.531 (4) |
N1—N2 | 1.372 (2) | C17—C18 | 1.541 (3) |
N2—C3 | 1.370 (3) | C18—H18A | 0.97 |
N2—C12 | 1.460 (3) | C18—H18B | 0.97 |
N3—C14 | 1.359 (3) | C18—H18C | 0.97 |
N3—N4 | 1.377 (3) | C19—H19A | 0.97 |
N3—C12 | 1.455 (3) | C19—H19B | 0.97 |
N4—C16 | 1.334 (3) | C19—H19C | 0.97 |
C1—C2 | 1.396 (3) | C20—H20A | 0.97 |
C1—C4 | 1.506 (3) | C20—H20B | 0.97 |
C2—C3 | 1.371 (3) | C20—H20C | 0.97 |
C2—H2A | 0.94 | C21—C23 | 1.526 (4) |
C3—C8 | 1.527 (3) | C21—C22 | 1.529 (4) |
C4—C6 | 1.480 (7) | C21—C24 | 1.530 (4) |
C4—C7 | 1.490 (8) | C22—H22A | 0.97 |
C4—C5A | 1.493 (7) | C22—H22B | 0.97 |
C4—C7A | 1.496 (8) | C22—H22C | 0.97 |
C4—C5 | 1.566 (7) | C23—H23A | 0.97 |
C4—C6A | 1.567 (8) | C23—H23B | 0.97 |
C5—H5A | 0.97 | C23—H23C | 0.97 |
C5—H5B | 0.97 | C24—H24A | 0.97 |
C5—H5C | 0.97 | C24—H24B | 0.97 |
C6—H6A | 0.97 | C24—H24C | 0.97 |
C6—H6B | 0.97 | O1—C25 | 1.430 (3) |
C6—H6C | 0.97 | O1—C28 | 1.439 (3) |
C7—H7A | 0.97 | C25—C26 | 1.495 (5) |
C7—H7B | 0.97 | C25—H25A | 0.98 |
C7—H7C | 0.97 | C25—H25B | 0.98 |
C5A—H5AA | 0.97 | C26—C27 | 1.515 (5) |
C5A—H5AB | 0.97 | C26—H26A | 0.98 |
C5A—H5AC | 0.97 | C26—H26B | 0.98 |
C6A—H6AA | 0.97 | C27—C28 | 1.479 (5) |
C6A—H6AB | 0.97 | C27—H27A | 0.98 |
C6A—H6AC | 0.97 | C27—H27B | 0.98 |
C7A—H7AA | 0.97 | C28—H28A | 0.98 |
C7A—H7AB | 0.97 | C28—H28B | 0.98 |
C7A—H7AC | 0.97 | O2—C29 | 1.314 (8) |
C8—C11A | 1.44 (3) | O2—C32 | 1.475 (8) |
C8—C10 | 1.509 (6) | C29—C30 | 1.507 (8) |
C8—C9A | 1.52 (3) | C29—H29A | 0.98 |
C8—C11 | 1.533 (7) | C29—H29B | 0.98 |
C8—C9 | 1.536 (6) | C30—C31 | 1.630 (10) |
C8—C10A | 1.61 (2) | C30—H30A | 0.98 |
C9—H9A | 0.97 | C30—H30B | 0.98 |
C9—H9B | 0.97 | C31—C32 | 1.418 (10) |
C9—H9C | 0.97 | C31—H31A | 0.98 |
C10—H10A | 0.97 | C31—H31B | 0.98 |
C10—H10B | 0.97 | C32—H32A | 0.98 |
C10—H10C | 0.97 | C32—H32B | 0.98 |
C11—H11A | 0.97 | O2A—C29A | 1.361 (14) |
C11—H11B | 0.97 | O2A—C32A | 1.511 (15) |
C11—H11C | 0.97 | C29A—C30A | 1.511 (14) |
C9A—H9A1 | 0.97 | C29A—H29C | 0.98 |
C9A—H9A2 | 0.97 | C29A—H29D | 0.98 |
C9A—H9A3 | 0.97 | C30A—C31A | 1.641 (15) |
C10A—H10D | 0.97 | C30A—H30C | 0.98 |
C10A—H10E | 0.97 | C30A—H30D | 0.98 |
C10A—H10F | 0.97 | C31A—C32A | 1.354 (15) |
C11A—H11D | 0.97 | C31A—H31C | 0.98 |
C11A—H11E | 0.97 | C31A—H31D | 0.98 |
C11A—H11F | 0.97 | C32A—H32C | 0.98 |
C12—C13 | 1.550 (3) | C32A—H32D | 0.98 |
C12—H12A | 0.99 | ||
C13—S1—Li1 | 89.79 (12) | N4—C16—C21 | 120.4 (2) |
C1—N1—N2 | 105.28 (17) | C15—C16—C21 | 129.5 (2) |
C1—N1—Li1 | 132.83 (19) | C14—C17—C20 | 108.2 (2) |
N2—N1—Li1 | 106.99 (17) | C14—C17—C19 | 112.3 (2) |
C3—N2—N1 | 111.66 (17) | C20—C17—C19 | 107.6 (2) |
C3—N2—C12 | 130.00 (19) | C14—C17—C18 | 109.5 (2) |
N1—N2—C12 | 118.33 (17) | C20—C17—C18 | 107.5 (2) |
C14—N3—N4 | 112.00 (18) | C19—C17—C18 | 111.6 (2) |
C14—N3—C12 | 130.7 (2) | C17—C18—H18A | 109.5 |
N4—N3—C12 | 117.12 (18) | C17—C18—H18B | 109.5 |
C16—N4—N3 | 104.96 (19) | H18A—C18—H18B | 109.5 |
C16—N4—Li1 | 137.3 (2) | C17—C18—H18C | 109.5 |
N3—N4—Li1 | 110.76 (17) | H18A—C18—H18C | 109.5 |
N1—C1—C2 | 110.4 (2) | H18B—C18—H18C | 109.5 |
N1—C1—C4 | 121.0 (2) | C17—C19—H19A | 109.5 |
C2—C1—C4 | 128.6 (2) | C17—C19—H19B | 109.5 |
C3—C2—C1 | 107.3 (2) | H19A—C19—H19B | 109.5 |
C3—C2—H2A | 126.3 | C17—C19—H19C | 109.5 |
C1—C2—H2A | 126.3 | H19A—C19—H19C | 109.5 |
N2—C3—C2 | 105.3 (2) | H19B—C19—H19C | 109.5 |
N2—C3—C8 | 127.4 (2) | C17—C20—H20A | 109.5 |
C2—C3—C8 | 127.2 (2) | C17—C20—H20B | 109.5 |
C6—C4—C7 | 112.4 (6) | H20A—C20—H20B | 109.5 |
C6—C4—C5A | 57.9 (6) | C17—C20—H20C | 109.5 |
C7—C4—C5A | 133.7 (5) | H20A—C20—H20C | 109.5 |
C6—C4—C7A | 136.1 (5) | H20B—C20—H20C | 109.5 |
C7—C4—C7A | 39.2 (5) | C16—C21—C23 | 109.3 (2) |
C5A—C4—C7A | 112.5 (6) | C16—C21—C22 | 109.8 (2) |
C6—C4—C1 | 111.2 (3) | C23—C21—C22 | 110.2 (2) |
C7—C4—C1 | 113.4 (4) | C16—C21—C24 | 109.4 (2) |
C5A—C4—C1 | 111.8 (4) | C23—C21—C24 | 109.7 (2) |
C7A—C4—C1 | 111.7 (4) | C22—C21—C24 | 108.4 (2) |
C6—C4—C5 | 105.8 (6) | C21—C22—H22A | 109.5 |
C7—C4—C5 | 107.5 (6) | C21—C22—H22B | 109.5 |
C5A—C4—C5 | 49.2 (5) | H22A—C22—H22B | 109.5 |
C7A—C4—C5 | 70.7 (5) | C21—C22—H22C | 109.5 |
C1—C4—C5 | 106.1 (3) | H22A—C22—H22C | 109.5 |
C6—C4—C6A | 51.1 (5) | H22B—C22—H22C | 109.5 |
C7—C4—C6A | 69.1 (6) | C21—C23—H23A | 109.5 |
C5A—C4—C6A | 107.1 (6) | C21—C23—H23B | 109.5 |
C7A—C4—C6A | 107.0 (5) | H23A—C23—H23B | 109.5 |
C1—C4—C6A | 106.3 (3) | C21—C23—H23C | 109.5 |
C5—C4—C6A | 145.7 (4) | H23A—C23—H23C | 109.5 |
C4—C5—H5A | 109.5 | H23B—C23—H23C | 109.5 |
C4—C5—H5B | 109.5 | C21—C24—H24A | 109.5 |
C4—C5—H5C | 109.5 | C21—C24—H24B | 109.5 |
C4—C6—H6A | 109.5 | H24A—C24—H24B | 109.5 |
C4—C6—H6B | 109.5 | C21—C24—H24C | 109.5 |
C4—C6—H6C | 109.5 | H24A—C24—H24C | 109.5 |
C4—C7—H7A | 109.5 | H24B—C24—H24C | 109.5 |
C4—C7—H7B | 109.5 | O1—Li1—N4 | 126.2 (2) |
C4—C7—H7C | 109.5 | O1—Li1—N1 | 138.4 (2) |
C4—C5A—H5AA | 109.5 | N4—Li1—N1 | 87.65 (17) |
C4—C5A—H5AB | 109.5 | O1—Li1—S1 | 104.01 (17) |
H5AA—C5A—H5AB | 109.5 | N4—Li1—S1 | 96.71 (17) |
C4—C5A—H5AC | 109.5 | N1—Li1—S1 | 93.64 (16) |
H5AA—C5A—H5AC | 109.5 | C25—O1—C28 | 104.7 (2) |
H5AB—C5A—H5AC | 109.5 | C25—O1—Li1 | 117.9 (2) |
C4—C6A—H6AA | 109.5 | C28—O1—Li1 | 137.3 (2) |
C4—C6A—H6AB | 109.5 | O1—C25—C26 | 106.9 (3) |
H6AA—C6A—H6AB | 109.5 | O1—C25—H25A | 110.3 |
C4—C6A—H6AC | 109.5 | C26—C25—H25A | 110.3 |
H6AA—C6A—H6AC | 109.5 | O1—C25—H25B | 110.3 |
H6AB—C6A—H6AC | 109.5 | C26—C25—H25B | 110.3 |
C4—C7A—H7AA | 109.5 | H25A—C25—H25B | 108.6 |
C4—C7A—H7AB | 109.5 | C25—C26—C27 | 104.5 (3) |
H7AA—C7A—H7AB | 109.5 | C25—C26—H26A | 110.9 |
C4—C7A—H7AC | 109.5 | C27—C26—H26A | 110.9 |
H7AA—C7A—H7AC | 109.5 | C25—C26—H26B | 110.9 |
H7AB—C7A—H7AC | 109.5 | C27—C26—H26B | 110.9 |
C11A—C8—C10 | 131.9 (12) | H26A—C26—H26B | 108.9 |
C11A—C8—C9A | 107.1 (17) | C28—C27—C26 | 104.5 (3) |
C10—C8—C9A | 78.9 (14) | C28—C27—H27A | 110.9 |
C11A—C8—C3 | 109.0 (11) | C26—C27—H27A | 110.9 |
C10—C8—C3 | 113.6 (3) | C28—C27—H27B | 110.9 |
C9A—C8—C3 | 109.5 (12) | C26—C27—H27B | 110.9 |
C11A—C8—C11 | 30.6 (13) | H27A—C27—H27B | 108.9 |
C10—C8—C11 | 110.4 (4) | O1—C28—C27 | 105.0 (3) |
C9A—C8—C11 | 130.3 (15) | O1—C28—H28A | 110.8 |
C3—C8—C11 | 110.2 (3) | C27—C28—H28A | 110.8 |
C11A—C8—C9 | 78.7 (13) | O1—C28—H28B | 110.8 |
C10—C8—C9 | 108.3 (4) | C27—C28—H28B | 110.8 |
C9A—C8—C9 | 31.7 (15) | H28A—C28—H28B | 108.8 |
C3—C8—C9 | 106.9 (3) | C29—O2—C32 | 112.3 (5) |
C11—C8—C9 | 107.2 (4) | O2—C29—C30 | 107.9 (7) |
C11A—C8—C10A | 106.7 (14) | O2—C29—H29A | 110.1 |
C10—C8—C10A | 32.1 (9) | C30—C29—H29A | 110.1 |
C9A—C8—C10A | 106.3 (13) | O2—C29—H29B | 110.1 |
C3—C8—C10A | 117.7 (8) | C30—C29—H29B | 110.1 |
C11—C8—C10A | 80.0 (10) | H29A—C29—H29B | 108.4 |
C9—C8—C10A | 129.1 (9) | C29—C30—C31 | 97.7 (6) |
C8—C9—H9A | 109.5 | C29—C30—H30A | 112.2 |
C8—C9—H9B | 109.5 | C31—C30—H30A | 112.2 |
C8—C9—H9C | 109.5 | C29—C30—H30B | 112.2 |
C8—C10—H10A | 109.5 | C31—C30—H30B | 112.2 |
C8—C10—H10B | 109.5 | H30A—C30—H30B | 109.8 |
C8—C10—H10C | 109.5 | C32—C31—C30 | 100.1 (7) |
C8—C11—H11A | 109.5 | C32—C31—H31A | 111.7 |
C8—C11—H11B | 109.5 | C30—C31—H31A | 111.8 |
C8—C11—H11C | 109.5 | C32—C31—H31B | 111.8 |
C8—C9A—H9A1 | 109.5 | C30—C31—H31B | 111.8 |
C8—C9A—H9A2 | 109.5 | H31A—C31—H31B | 109.5 |
H9A1—C9A—H9A2 | 109.5 | C31—C32—O2 | 100.8 (7) |
C8—C9A—H9A3 | 109.5 | C31—C32—H32A | 111.6 |
H9A1—C9A—H9A3 | 109.5 | O2—C32—H32A | 111.6 |
H9A2—C9A—H9A3 | 109.5 | C31—C32—H32B | 111.6 |
C8—C10A—H10D | 109.5 | O2—C32—H32B | 111.6 |
C8—C10A—H10E | 109.5 | H32A—C32—H32B | 109.4 |
H10D—C10A—H10E | 109.5 | C29A—O2A—C32A | 106.4 (11) |
C8—C10A—H10F | 109.5 | O2A—C29A—C30A | 103.7 (12) |
H10D—C10A—H10F | 109.5 | O2A—C29A—H29C | 111 |
H10E—C10A—H10F | 109.5 | C30A—C29A—H29C | 111 |
C8—C11A—H11D | 109.5 | O2A—C29A—H29D | 111 |
C8—C11A—H11E | 109.5 | C30A—C29A—H29D | 111 |
H11D—C11A—H11E | 109.5 | H29C—C29A—H29D | 109 |
C8—C11A—H11F | 109.5 | C29A—C30A—C31A | 90.4 (11) |
H11D—C11A—H11F | 109.5 | C29A—C30A—H30C | 113.6 |
H11E—C11A—H11F | 109.5 | C31A—C30A—H30C | 113.6 |
N3—C12—N2 | 110.54 (17) | C29A—C30A—H30D | 113.6 |
N3—C12—C13 | 109.69 (17) | C31A—C30A—H30D | 113.6 |
N2—C12—C13 | 115.51 (19) | H30C—C30A—H30D | 110.8 |
N3—C12—H12A | 106.9 | C32A—C31A—C30A | 106.0 (11) |
N2—C12—H12A | 106.9 | C32A—C31A—H31C | 110.6 |
C13—C12—H12A | 106.9 | C30A—C31A—H31C | 110.5 |
C12—C13—S2 | 113.64 (17) | C32A—C31A—H31D | 110.5 |
C12—C13—S1 | 118.61 (17) | C30A—C31A—H31D | 110.5 |
S2—C13—S1 | 127.75 (14) | H31C—C31A—H31D | 108.7 |
N3—C14—C15 | 105.4 (2) | C31A—C32A—O2A | 104.1 (11) |
N3—C14—C17 | 126.3 (2) | C31A—C32A—H32C | 110.9 |
C15—C14—C17 | 128.2 (2) | O2A—C32A—H32C | 110.9 |
C14—C15—C16 | 107.5 (2) | C31A—C32A—H32D | 110.9 |
C14—C15—H15A | 126.3 | O2A—C32A—H32D | 110.9 |
C16—C15—H15A | 126.3 | H32C—C32A—H32D | 109 |
N4—C16—C15 | 110.1 (2) |
[Zn(C24H39N4S2)Cl] | F(000) = 1160 |
Mr = 548.53 | Dx = 1.314 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 238 reflections |
a = 14.2713 (19) Å | θ = 6–20° |
b = 11.9298 (17) Å | µ = 1.15 mm−1 |
c = 16.8543 (12) Å | T = 150 K |
β = 104.919 (8)° | Prism, clear light red |
V = 2772.8 (6) Å3 | 0.18 × 0.18 × 0.14 mm |
Z = 4 |
Bruker–Nonius KappaCCD diffractometer | 7007 independent reflections |
Graphite monochromator | 5579 reflections with I > 2σ(I) |
Detector resolution: 9 pixels mm-1 | Rint = 0.040 |
ϕ– and ω–rotations with 2.00 ° and 120 sec per frame scans | θmax = 28.5°, θmin = 3.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −19→19 |
Tmin = 0.740, Tmax = 0.85 | k = −16→16 |
68182 measured reflections | l = −22→22 |
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)] = 0.027 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.075 | H-atom parameters constrained |
S = 1.12 | w = 1/[σ2(Fo2) + (0.0322P)2 + 1.3233P] where P = (Fo2 + 2Fc2)/3 |
7007 reflections | (Δ/σ)max = 0.001 |
289 parameters | Δρmax = 0.41 e Å−3 |
0 restraints | Δρmin = −0.38 e Å−3 |
[Zn(C24H39N4S2)Cl] | V = 2772.8 (6) Å3 |
Mr = 548.53 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 14.2713 (19) Å | µ = 1.15 mm−1 |
b = 11.9298 (17) Å | T = 150 K |
c = 16.8543 (12) Å | 0.18 × 0.18 × 0.14 mm |
β = 104.919 (8)° |
Bruker–Nonius KappaCCD diffractometer | 7007 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | 5579 reflections with I > 2σ(I) |
Tmin = 0.740, Tmax = 0.85 | Rint = 0.040 |
68182 measured reflections |
R[F2 > 2σ(F2)] = 0.027 | 0 restraints |
wR(F2) = 0.075 | H-atom parameters constrained |
S = 1.12 | Δρmax = 0.41 e Å−3 |
7007 reflections | Δρmin = −0.38 e Å−3 |
289 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
Zn | 0.399158 (13) | 0.002463 (16) | 0.179063 (11) | 0.01772 (6) | |
S1 | 0.50065 (3) | 0.14913 (3) | 0.23984 (3) | 0.02247 (9) | |
Cl1 | 0.28048 (3) | 0.03791 (4) | 0.07121 (3) | 0.02954 (10) | |
S2 | 0.62476 (4) | 0.13051 (4) | 0.41197 (3) | 0.02826 (10) | |
N12 | 0.58399 (9) | −0.08936 (11) | 0.23786 (8) | 0.0147 (2) | |
N21 | 0.39162 (10) | −0.06311 (11) | 0.28961 (8) | 0.0179 (3) | |
C14 | 0.66718 (11) | −0.09750 (12) | 0.21208 (9) | 0.0154 (3) | |
N22 | 0.48081 (9) | −0.10527 (11) | 0.33078 (8) | 0.0165 (3) | |
C2 | 0.56349 (11) | 0.07628 (13) | 0.32396 (10) | 0.0180 (3) | |
C12 | 0.53931 (11) | −0.16156 (13) | 0.11602 (9) | 0.0171 (3) | |
C23 | 0.37361 (12) | −0.19120 (14) | 0.38172 (10) | 0.0204 (3) | |
H23 | 0.3435 | −0.2389 | 0.413 | 0.024* | |
C21 | 0.21892 (12) | −0.08815 (14) | 0.29195 (10) | 0.0200 (3) | |
N11 | 0.50429 (9) | −0.12432 (11) | 0.17799 (8) | 0.0170 (3) | |
C22 | 0.32635 (11) | −0.11457 (13) | 0.32109 (9) | 0.0171 (3) | |
C15B | 0.80332 (14) | −0.08969 (18) | 0.34548 (11) | 0.0323 (4) | |
H15A | 0.7644 | −0.0525 | 0.3779 | 0.048* | |
H15B | 0.8716 | −0.0686 | 0.3667 | 0.048* | |
H15C | 0.7968 | −0.1711 | 0.3494 | 0.048* | |
C13 | 0.63954 (12) | −0.14540 (14) | 0.13506 (10) | 0.0194 (3) | |
H13 | 0.6811 | −0.164 | 0.1012 | 0.023* | |
C15 | 0.76767 (11) | −0.05344 (13) | 0.25537 (10) | 0.0181 (3) | |
C11 | 0.47595 (12) | −0.22017 (15) | 0.04136 (10) | 0.0226 (3) | |
C21B | 0.20337 (13) | 0.03817 (15) | 0.27724 (12) | 0.0282 (4) | |
H21A | 0.2334 | 0.0789 | 0.3279 | 0.042* | |
H21B | 0.1337 | 0.0544 | 0.2607 | 0.042* | |
H21C | 0.2331 | 0.062 | 0.2337 | 0.042* | |
C24 | 0.47132 (12) | −0.18433 (13) | 0.38740 (9) | 0.0175 (3) | |
C25 | 0.55343 (12) | −0.25046 (14) | 0.44289 (10) | 0.0215 (3) | |
C15C | 0.76737 (12) | 0.07563 (14) | 0.24991 (11) | 0.0224 (3) | |
H15D | 0.7421 | 0.0987 | 0.1926 | 0.034* | |
H15E | 0.8337 | 0.1038 | 0.2707 | 0.034* | |
H15F | 0.7261 | 0.1064 | 0.283 | 0.034* | |
C25A | 0.61589 (14) | −0.30780 (16) | 0.39239 (12) | 0.0296 (4) | |
H25A | 0.575 | −0.3574 | 0.3514 | 0.044* | |
H25B | 0.6671 | −0.3518 | 0.4291 | 0.044* | |
H25C | 0.6452 | −0.2506 | 0.3646 | 0.044* | |
C3 | 0.56773 (11) | −0.05290 (13) | 0.31698 (9) | 0.0156 (3) | |
H3 | 0.6242 | −0.0795 | 0.3614 | 0.019* | |
C15A | 0.83961 (12) | −0.09765 (16) | 0.20881 (13) | 0.0300 (4) | |
H15G | 0.8396 | −0.1798 | 0.2096 | 0.045* | |
H15H | 0.9048 | −0.07 | 0.2353 | 0.045* | |
H15I | 0.8203 | −0.0713 | 0.1518 | 0.045* | |
C25B | 0.61513 (13) | −0.17492 (16) | 0.51056 (10) | 0.0276 (4) | |
H25D | 0.6452 | −0.1155 | 0.4854 | 0.041* | |
H25E | 0.6658 | −0.2199 | 0.5471 | 0.041* | |
H25F | 0.5737 | −0.1413 | 0.5423 | 0.041* | |
C25C | 0.50885 (14) | −0.34436 (16) | 0.48452 (11) | 0.0300 (4) | |
H25G | 0.4716 | −0.311 | 0.5199 | 0.045* | |
H25H | 0.5608 | −0.3912 | 0.5177 | 0.045* | |
H25I | 0.4658 | −0.3905 | 0.4424 | 0.045* | |
C21A | 0.17509 (13) | −0.15255 (16) | 0.21164 (11) | 0.0266 (4) | |
H21D | 0.2068 | −0.1285 | 0.1694 | 0.04* | |
H21E | 0.1054 | −0.137 | 0.1932 | 0.04* | |
H21F | 0.1852 | −0.2332 | 0.2213 | 0.04* | |
C21C | 0.16894 (13) | −0.12494 (18) | 0.35828 (11) | 0.0296 (4) | |
H21G | 0.1766 | −0.206 | 0.3668 | 0.044* | |
H21H | 0.0998 | −0.1063 | 0.3406 | 0.044* | |
H21I | 0.1986 | −0.0859 | 0.4098 | 0.044* | |
C11A | 0.38321 (16) | −0.2628 (2) | 0.05872 (13) | 0.0405 (5) | |
H11A | 0.3991 | −0.3137 | 0.1059 | 0.061* | |
H11B | 0.3449 | −0.303 | 0.0105 | 0.061* | |
H11C | 0.3457 | −0.1993 | 0.071 | 0.061* | |
C11B | 0.45095 (19) | −0.1394 (2) | −0.03125 (12) | 0.0526 (7) | |
H11D | 0.4125 | −0.077 | −0.0186 | 0.079* | |
H11E | 0.4134 | −0.179 | −0.0801 | 0.079* | |
H11F | 0.5109 | −0.1103 | −0.0417 | 0.079* | |
C11C | 0.53461 (19) | −0.3171 (3) | 0.01992 (18) | 0.0717 (10) | |
H11G | 0.5943 | −0.2881 | 0.009 | 0.108* | |
H11H | 0.4962 | −0.3557 | −0.029 | 0.108* | |
H11I | 0.551 | −0.3699 | 0.066 | 0.108* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn | 0.01461 (9) | 0.02165 (10) | 0.01642 (9) | 0.00101 (7) | 0.00313 (7) | 0.00275 (7) |
S1 | 0.0210 (2) | 0.01768 (19) | 0.0272 (2) | 0.00017 (15) | 0.00355 (16) | 0.00220 (16) |
Cl1 | 0.0225 (2) | 0.0390 (2) | 0.0228 (2) | 0.00450 (18) | −0.00179 (16) | 0.00517 (18) |
S2 | 0.0370 (3) | 0.0275 (2) | 0.0197 (2) | −0.00485 (19) | 0.00642 (18) | −0.00877 (17) |
N12 | 0.0139 (6) | 0.0174 (6) | 0.0125 (6) | 0.0006 (5) | 0.0025 (5) | −0.0007 (5) |
N21 | 0.0150 (6) | 0.0221 (7) | 0.0165 (6) | 0.0002 (5) | 0.0042 (5) | 0.0007 (5) |
C14 | 0.0152 (7) | 0.0137 (7) | 0.0174 (7) | 0.0006 (6) | 0.0046 (6) | 0.0019 (6) |
N22 | 0.0154 (6) | 0.0203 (6) | 0.0140 (6) | 0.0005 (5) | 0.0042 (5) | 0.0010 (5) |
C2 | 0.0167 (8) | 0.0211 (8) | 0.0183 (7) | −0.0007 (6) | 0.0081 (6) | −0.0023 (6) |
C12 | 0.0199 (8) | 0.0166 (7) | 0.0146 (7) | 0.0000 (6) | 0.0042 (6) | −0.0001 (6) |
C23 | 0.0236 (8) | 0.0214 (8) | 0.0182 (7) | −0.0029 (6) | 0.0090 (6) | −0.0005 (6) |
C21 | 0.0160 (8) | 0.0248 (8) | 0.0202 (8) | −0.0028 (6) | 0.0065 (6) | −0.0036 (6) |
N11 | 0.0152 (6) | 0.0201 (6) | 0.0146 (6) | −0.0010 (5) | 0.0015 (5) | −0.0024 (5) |
C22 | 0.0183 (8) | 0.0191 (7) | 0.0153 (7) | −0.0029 (6) | 0.0067 (6) | −0.0051 (6) |
C15B | 0.0225 (9) | 0.0400 (11) | 0.0280 (9) | −0.0056 (8) | −0.0051 (7) | 0.0127 (8) |
C13 | 0.0192 (8) | 0.0230 (8) | 0.0171 (7) | −0.0002 (6) | 0.0067 (6) | −0.0012 (6) |
C15 | 0.0132 (7) | 0.0186 (8) | 0.0213 (8) | −0.0002 (6) | 0.0021 (6) | 0.0019 (6) |
C11 | 0.0214 (8) | 0.0284 (9) | 0.0173 (7) | −0.0037 (7) | 0.0034 (6) | −0.0060 (7) |
C21B | 0.0212 (9) | 0.0268 (9) | 0.0382 (10) | 0.0025 (7) | 0.0106 (8) | −0.0042 (8) |
C24 | 0.0229 (8) | 0.0172 (7) | 0.0129 (7) | −0.0012 (6) | 0.0056 (6) | −0.0013 (6) |
C25 | 0.0242 (8) | 0.0219 (8) | 0.0192 (8) | 0.0039 (6) | 0.0071 (7) | 0.0034 (6) |
C15C | 0.0183 (8) | 0.0209 (8) | 0.0292 (9) | −0.0028 (6) | 0.0081 (7) | −0.0002 (7) |
C25A | 0.0354 (10) | 0.0253 (9) | 0.0315 (9) | 0.0090 (8) | 0.0146 (8) | 0.0036 (8) |
C3 | 0.0160 (7) | 0.0185 (7) | 0.0126 (7) | 0.0002 (6) | 0.0040 (6) | −0.0009 (6) |
C15A | 0.0152 (8) | 0.0308 (9) | 0.0446 (11) | 0.0014 (7) | 0.0089 (8) | −0.0065 (8) |
C25B | 0.0263 (9) | 0.0350 (10) | 0.0196 (8) | 0.0035 (8) | 0.0026 (7) | 0.0040 (7) |
C25C | 0.0357 (11) | 0.0265 (9) | 0.0293 (9) | 0.0034 (8) | 0.0111 (8) | 0.0101 (7) |
C21A | 0.0227 (9) | 0.0333 (9) | 0.0228 (8) | −0.0071 (7) | 0.0040 (7) | −0.0045 (7) |
C21C | 0.0209 (9) | 0.0439 (11) | 0.0263 (9) | −0.0042 (8) | 0.0104 (7) | −0.0015 (8) |
C11A | 0.0413 (12) | 0.0524 (13) | 0.0291 (10) | −0.0285 (10) | 0.0117 (9) | −0.0126 (9) |
C11B | 0.0663 (16) | 0.0640 (16) | 0.0189 (9) | −0.0350 (13) | −0.0044 (10) | 0.0052 (10) |
C11C | 0.0425 (14) | 0.0786 (19) | 0.0775 (19) | 0.0162 (13) | −0.0143 (13) | −0.0620 (17) |
Zn—N21 | 2.0490 (13) | C21B—H21B | 0.98 |
Zn—N11 | 2.1338 (13) | C21B—H21C | 0.98 |
Zn—Cl1 | 2.1832 (5) | C24—C25 | 1.519 (2) |
Zn—S1 | 2.3335 (5) | C25—C25B | 1.540 (2) |
S1—C2 | 1.7073 (17) | C25—C25A | 1.542 (2) |
S2—C2 | 1.6480 (16) | C25—C25C | 1.543 (2) |
N12—C14 | 1.3686 (19) | C15C—H15D | 0.98 |
N12—N11 | 1.3766 (17) | C15C—H15E | 0.98 |
N12—C3 | 1.4768 (19) | C15C—H15F | 0.98 |
N21—C22 | 1.334 (2) | C25A—H25A | 0.98 |
N21—N22 | 1.3784 (18) | C25A—H25B | 0.98 |
C14—C13 | 1.380 (2) | C25A—H25C | 0.98 |
C14—C15 | 1.525 (2) | C3—H3 | 1 |
N22—C24 | 1.373 (2) | C15A—H15G | 0.98 |
N22—C3 | 1.460 (2) | C15A—H15H | 0.98 |
C2—C3 | 1.548 (2) | C15A—H15I | 0.98 |
C12—N11 | 1.344 (2) | C25B—H25D | 0.98 |
C12—C13 | 1.396 (2) | C25B—H25E | 0.98 |
C12—C11 | 1.518 (2) | C25B—H25F | 0.98 |
C23—C24 | 1.375 (2) | C25C—H25G | 0.98 |
C23—C22 | 1.407 (2) | C25C—H25H | 0.98 |
C23—H23 | 0.95 | C25C—H25I | 0.98 |
C21—C22 | 1.518 (2) | C21A—H21D | 0.98 |
C21—C21B | 1.534 (2) | C21A—H21E | 0.98 |
C21—C21C | 1.537 (2) | C21A—H21F | 0.98 |
C21—C21A | 1.542 (2) | C21C—H21G | 0.98 |
C15B—C15 | 1.534 (2) | C21C—H21H | 0.98 |
C15B—H15A | 0.98 | C21C—H21I | 0.98 |
C15B—H15B | 0.98 | C11A—H11A | 0.98 |
C15B—H15C | 0.98 | C11A—H11B | 0.98 |
C13—H13 | 0.95 | C11A—H11C | 0.98 |
C15—C15A | 1.537 (2) | C11B—H11D | 0.98 |
C15—C15C | 1.542 (2) | C11B—H11E | 0.98 |
C11—C11A | 1.515 (3) | C11B—H11F | 0.98 |
C11—C11C | 1.525 (3) | C11C—H11G | 0.98 |
C11—C11B | 1.526 (3) | C11C—H11H | 0.98 |
C21B—H21A | 0.98 | C11C—H11I | 0.98 |
N21—Zn—N11 | 86.49 (5) | C24—C25—C25A | 110.77 (13) |
N21—Zn—S1 | 93.39 (4) | C25B—C25—C25A | 111.53 (15) |
N11—Zn—S1 | 100.19 (4) | C24—C25—C25C | 108.30 (14) |
Cl1—Zn—S1 | 118.76 (2) | C25B—C25—C25C | 108.19 (14) |
N21—Zn—Cl1 | 128.32 (4) | C25A—C25—C25C | 107.07 (14) |
N11—Zn—Cl1 | 121.78 (4) | C15—C15C—H15D | 109.5 |
C2—S1—Zn | 96.71 (6) | C15—C15C—H15E | 109.5 |
C14—N12—N11 | 111.49 (12) | H15D—C15C—H15E | 109.5 |
C14—N12—C3 | 131.18 (13) | C15—C15C—H15F | 109.5 |
N11—N12—C3 | 117.31 (12) | H15D—C15C—H15F | 109.5 |
C22—N21—N22 | 106.31 (13) | H15E—C15C—H15F | 109.5 |
C22—N21—Zn | 137.95 (11) | C25—C25A—H25A | 109.5 |
N22—N21—Zn | 109.83 (9) | C25—C25A—H25B | 109.5 |
N12—C14—C13 | 105.47 (13) | H25A—C25A—H25B | 109.5 |
N12—C14—C15 | 127.54 (14) | C25—C25A—H25C | 109.5 |
C13—C14—C15 | 126.77 (14) | H25A—C25A—H25C | 109.5 |
C24—N22—N21 | 110.91 (12) | H25B—C25A—H25C | 109.5 |
C24—N22—C3 | 130.14 (13) | N22—C3—N12 | 110.81 (12) |
N21—N22—C3 | 118.43 (12) | N22—C3—C2 | 111.26 (13) |
C3—C2—S2 | 115.92 (11) | N12—C3—C2 | 112.34 (12) |
C3—C2—S1 | 117.79 (11) | N22—C3—H3 | 107.4 |
S2—C2—S1 | 126.24 (10) | N12—C3—H3 | 107.4 |
N11—C12—C13 | 109.86 (14) | C2—C3—H3 | 107.4 |
N11—C12—C11 | 122.35 (14) | C15—C15A—H15G | 109.5 |
C13—C12—C11 | 127.62 (14) | C15—C15A—H15H | 109.5 |
C24—C23—C22 | 107.43 (14) | H15G—C15A—H15H | 109.5 |
C24—C23—H23 | 126.3 | C15—C15A—H15I | 109.5 |
C22—C23—H23 | 126.3 | H15G—C15A—H15I | 109.5 |
C22—C21—C21B | 110.38 (13) | H15H—C15A—H15I | 109.5 |
C22—C21—C21C | 108.95 (14) | C25—C25B—H25D | 109.5 |
C21B—C21—C21C | 108.86 (14) | C25—C25B—H25E | 109.5 |
C22—C21—C21A | 109.16 (13) | H25D—C25B—H25E | 109.5 |
C21B—C21—C21A | 109.78 (15) | C25—C25B—H25F | 109.5 |
C21C—C21—C21A | 109.69 (14) | H25D—C25B—H25F | 109.5 |
C12—N11—N12 | 105.50 (12) | H25E—C25B—H25F | 109.5 |
C12—N11—Zn | 130.08 (11) | C25—C25C—H25G | 109.5 |
N12—N11—Zn | 103.25 (9) | C25—C25C—H25H | 109.5 |
N21—C22—C23 | 109.54 (14) | H25G—C25C—H25H | 109.5 |
N21—C22—C21 | 121.76 (14) | C25—C25C—H25I | 109.5 |
C23—C22—C21 | 128.70 (14) | H25G—C25C—H25I | 109.5 |
C15—C15B—H15A | 109.5 | H25H—C25C—H25I | 109.5 |
C15—C15B—H15B | 109.5 | C21—C21A—H21D | 109.5 |
H15A—C15B—H15B | 109.5 | C21—C21A—H21E | 109.5 |
C15—C15B—H15C | 109.5 | H21D—C21A—H21E | 109.5 |
H15A—C15B—H15C | 109.5 | C21—C21A—H21F | 109.5 |
H15B—C15B—H15C | 109.5 | H21D—C21A—H21F | 109.5 |
C14—C13—C12 | 107.53 (14) | H21E—C21A—H21F | 109.5 |
C14—C13—H13 | 126.2 | C21—C21C—H21G | 109.5 |
C12—C13—H13 | 126.2 | C21—C21C—H21H | 109.5 |
C14—C15—C15B | 114.06 (13) | H21G—C21C—H21H | 109.5 |
C14—C15—C15A | 107.87 (13) | C21—C21C—H21I | 109.5 |
C15B—C15—C15A | 108.29 (15) | H21G—C21C—H21I | 109.5 |
C14—C15—C15C | 109.12 (13) | H21H—C21C—H21I | 109.5 |
C15B—C15—C15C | 109.60 (14) | C11—C11A—H11A | 109.5 |
C15A—C15—C15C | 107.70 (14) | C11—C11A—H11B | 109.5 |
C11A—C11—C12 | 110.99 (14) | H11A—C11A—H11B | 109.5 |
C11A—C11—C11C | 110.56 (19) | C11—C11A—H11C | 109.5 |
C12—C11—C11C | 107.44 (15) | H11A—C11A—H11C | 109.5 |
C11A—C11—C11B | 109.36 (17) | H11B—C11A—H11C | 109.5 |
C12—C11—C11B | 109.89 (15) | C11—C11B—H11D | 109.5 |
C11C—C11—C11B | 108.6 (2) | C11—C11B—H11E | 109.5 |
C21—C21B—H21A | 109.5 | H11D—C11B—H11E | 109.5 |
C21—C21B—H21B | 109.5 | C11—C11B—H11F | 109.5 |
H21A—C21B—H21B | 109.5 | H11D—C11B—H11F | 109.5 |
C21—C21B—H21C | 109.5 | H11E—C11B—H11F | 109.5 |
H21A—C21B—H21C | 109.5 | C11—C11C—H11G | 109.5 |
H21B—C21B—H21C | 109.5 | C11—C11C—H11H | 109.5 |
N22—C24—C23 | 105.80 (14) | H11G—C11C—H11H | 109.5 |
N22—C24—C25 | 125.89 (14) | C11—C11C—H11I | 109.5 |
C23—C24—C25 | 128.30 (14) | H11G—C11C—H11I | 109.5 |
C24—C25—C25B | 110.83 (14) | H11H—C11C—H11I | 109.5 |
S1—Li1 | 2.492 (4) | Li1—O1 | 1.957 (5) |
N1—Li1 | 2.085 (4) | S1—C13 | 1.675 (3) |
N4—Li1 | 2.060 (5) | S2—C13 | 1.660 (2) |
O1—Li1—N4 | 126.2 (2) | O1—Li1—S1 | 104.01 (17) |
O1—Li1—N1 | 138.4 (2) | N4—Li1—S1 | 96.71 (17) |
N4—Li1—N1 | 87.65 (17) | N1—Li1—S1 | 93.64 (16) |
Zn—N21 | 2.0490 (13) | Zn—Cl1 | 2.1832 (5) |
Zn—N11 | 2.1338 (13) | Zn—S1 | 2.3335 (5) |
N21—Zn—N11 | 86.49 (5) | Cl1—Zn—S1 | 118.76 (2) |
N21—Zn—S1 | 93.39 (4) | N21—Zn—Cl1 | 128.32 (4) |
N11—Zn—S1 | 100.19 (4) | N11—Zn—Cl1 | 121.78 (4) |