Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270113023524/sk3509sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270113023524/sk3509Isup2.hkl |
CCDC reference: 969446
Bis(benzthiazolines) undergo rearrangement by certain metal ions to yield a Schiff base chelate (Jadamus et al., 1964). The synthesis of the complex bis(diacetyl)bis(2-mercaptoanil)zinc(II) or {2,2'-[(butane-2,3-diylidene)bis(azanylylidene)]dibenzenethiolato}zinc(II), Zn(o-SPhNCMe)2, was reported on the basis of elemental analysis and electronic absorption spectra to result in a monomeric complex consisting of a Schiff base chelated to a metal atom (Jadamus et al., 1964). The structure of the closely related complex Zn(o-SPhNHCHMe).MeOH, for which the solid-state structure had been obtained, was also reported as being monomeric (Tsagkalidis & Rehder, 1996). This complex displayed an S—Zn—S angle of 141.15 (7)° and a hydrogen bond between one of the Zn-coordinated thiolate S atoms and the –OH group of the methanol solvent molecule. It was noted that `biologically active zinc sites in enzymes tend to vary between tetra- and pentacoordination in geometrical arrangements largely deviating from ideal polyhedral' (Tsagkalidis & Rehder, 1996). A monomer was also evident in the crystal structure of Zn(o-SPhNHCH2)2 (Shaban, 2011) and this complex did feature an S—Zn—S angle of 138.20 (3)°. The reason for this, in both cases, is probably the twisted nature of the ethylenic group which can accommodate the aforementioned large S—Zn—S angle.
The title zinc complex was prepared according to the literature method of Jadamus et al. (1964) resulting in a fibrous red precipitate. Crystals of the material were grown by slow diffusion of methanol into a saturated solution of the compound in a mixture of DMSO and MeOH (1:1 v/v) using a straight glass tube.
Crystal data, data collection and structure refinement details are summarized in Table 1. The nature of the disordered solvent molecules was discerned via difference maps and the molecules (dimethyl sulfoxide and methanol) were refined with the sum of their occupancies constrained to unity. The O—H distance was restrained to be 0.84 (1) Å, with Uiso(H) = 1.5Ueq(O). Other H atoms were placed in calculated positions, with C—H distances of 0.98 and 0.95 Å for aromatic and methyl H atoms, and with Uiso(H) = 1.2Ueq(aromatic C) or 1.5Ueq(methyl C).
Crystals of the title compound, bis{µ-2,2'-[(butane-2,3-diylidene)bis(azanylylidene)]dibenzenethiolato}dizinc(II)–dimethyl sulfoxide–methanol (2/0.18/0.82), (I), were obtained during our examination of the Zn2+-ion-induced rearrangement of 2,2'-bis(2-methylbenzothiazoline) (see Scheme). The IR spectra of the ligand (after washing with H2O2) and that of (I) (Fig. 1), illustrate the disappearance of the ν(NH) stretch at 3387 cm-1, together with slight changes in the fingerprint region of the spectrum. We found that crystals of (I) had limited solubility which hindered characterization in solution.
In contrast to the findings for compounds closely related to Zn(o-SPhNCMe)2, and somewhat in disagreement with the claims that had been put forward for the complex itself in the report of Jadamus et al. (1964), we find that the title compound consists in the solid state of two Schiff base complexes linked together forming a dimeric Zn2S2 rhomboid, with the Zn atoms displaying distorted trigonal bipyramidal geometries (Fig. 2 and Table 2). The axial atoms and the angle for each Zn atom in the molecules are: N1—Zn1—S2 = 157.93 (12)°, N4—Zn2—S3 = 159.75 (12)°, N6—Zn3—S5 = 160.63 (11)° and N8—Zn4—S8 = 160.73 (12)° (Table 2). The τ parameters (a way of estimating the distortion with a perfect square-pyramidal geometry being 0 and trigonal bipyramidal being 1; Addison et al., 1984) for the Zn atoms are not equal, with the values for Zn1 and Zn2 being 0.36 and 0.37, respectively, whereas the values for Zn3 and Zn4 are 0.46 and 0.43, respectively. The equivalent S—Zn—S bond angles to those mentioned above are 115.47 (5), 111.68 (5), 112.05 (5) and 111.50 (5)° for Zn1–Zn4, respectively, and much smaller. These differences result in different orientations of the ligands in the two structures, as is evident in the imprecise overlay presented in Fig. 3. The Zn—S bond lengths within the Zn2S2 rhomboids in the two molecules average from 2.380 (9) and 2.49 (1) Å for the shorter and longer sides, respectively. The Zn—S(bidentate) distances are shorter and average 2.306 (7) Å (Table 2).
Similar to the structure of a related monomer (Tsagkalidis & Rehder, 1996), one of these S atoms, i.e., S6 is hydrogen bonded to a methanol solvent molecule refined to 81.9 (7)% occupancy with 18.1 (7)% occupied by a dimethyl sulfoxide molecule Table 3. The methanol O atom (O1B) is also involved in weak interactions with two other H atoms of an adjacent dimer (Table 3). The DMSO solvent molecule is also secured by weak hydrogen-bonding interactions, with atom O1A linked to H50 and H28 of adjacent dimers and atom S1A linked to H28. Additional weak interactions are also observed between adjacent dimers, as evidenced in the listings for atoms S1, S3 and S7 in Table 3. The acute and obtuse angles within the squares average 87.4 (3) and 92.6 (4)°, respectively, for the S- and Zn-centered angles in Zn1—S2—Zn2—S3, and are slightly more distorted at 86.1 (3) and 93.9 (6)° for the S- and Zn-centered angles in Zn3—S5—Zn4—S8. The two Zn—N bond lengths were significantly different at each Zn atom (Table 2). An intriguing aspect of the two molecules in the asymmetric unit is the fact that the two 2,2'-[(butane-2,3-diylidene)bis(azanylylidene)]dibenzenethiolate ligands are bonded on the same side (i.e. cis) to one another with respect to the Zn2S2 rhomboid. In this arrangement, there is a C2 axis located perpendicular to the Zn2S2 rhomboid. This is in contrast to other related structures where a trans arrangement, due to a center of inversion in the middle of the rhomboid, was observed (Anselmo et al., 2012; Almaraz et al., 2008; Buncic et al., 2010; Cowley et al., 2002; Shaban, 2011; Tuntulani et al., 1992).
Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SADABS (Bruker, 2008); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL-2013 (Sheldrick, 2013); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).
[Zn2(C16H14N2S2)2]2·0.18C2H6OS·0.82CH4O | Z = 2 |
Mr = 1495.4 | F(000) = 1532.7 |
Triclinic, P1 | Dx = 1.611 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71069 Å |
a = 11.757 (4) Å | Cell parameters from 5099 reflections |
b = 16.145 (6) Å | θ = 2.2–28.3° |
c = 17.376 (6) Å | µ = 1.87 mm−1 |
α = 92.254 (5)° | T = 100 K |
β = 91.897 (6)° | Plate, colorless |
γ = 110.427 (5)° | 0.25 × 0.23 × 0.01 mm |
V = 3084.6 (19) Å3 |
Bruker SMART APEX CCD diffractometer | 15164 independent reflections |
Radiation source: sealed x-ray tube | 10524 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.067 |
ω scans | θmax = 28.4°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −15→15 |
Tmin = 0.654, Tmax = 0.746 | k = −21→21 |
37532 measured reflections | l = −23→23 |
Refinement on F2 | 7 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.066 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.116 | w = 1/[σ2(Fo2) + 12.0817P] where P = (Fo2 + 2Fc2)/3 |
S = 1.11 | (Δ/σ)max = 0.001 |
15164 reflections | Δρmax = 0.73 e Å−3 |
814 parameters | Δρmin = −0.81 e Å−3 |
[Zn2(C16H14N2S2)2]2·0.18C2H6OS·0.82CH4O | γ = 110.427 (5)° |
Mr = 1495.4 | V = 3084.6 (19) Å3 |
Triclinic, P1 | Z = 2 |
a = 11.757 (4) Å | Mo Kα radiation |
b = 16.145 (6) Å | µ = 1.87 mm−1 |
c = 17.376 (6) Å | T = 100 K |
α = 92.254 (5)° | 0.25 × 0.23 × 0.01 mm |
β = 91.897 (6)° |
Bruker SMART APEX CCD diffractometer | 15164 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | 10524 reflections with I > 2σ(I) |
Tmin = 0.654, Tmax = 0.746 | Rint = 0.067 |
37532 measured reflections |
R[F2 > 2σ(F2)] = 0.066 | 7 restraints |
wR(F2) = 0.116 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | w = 1/[σ2(Fo2) + 12.0817P] where P = (Fo2 + 2Fc2)/3 |
15164 reflections | Δρmax = 0.73 e Å−3 |
814 parameters | Δρmin = −0.81 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Zn1 | 0.77100 (5) | 0.12340 (4) | 0.55796 (3) | 0.01389 (12) | |
Zn2 | 0.97449 (5) | 0.32972 (4) | 0.59098 (3) | 0.01453 (13) | |
N1 | 0.6854 (4) | 0.0531 (3) | 0.4533 (2) | 0.0137 (8) | |
N2 | 0.6109 (4) | 0.1590 (3) | 0.5387 (2) | 0.0128 (8) | |
N3 | 0.8779 (4) | 0.3881 (3) | 0.5159 (2) | 0.0137 (8) | |
N4 | 0.9705 (4) | 0.4426 (3) | 0.6570 (2) | 0.0137 (8) | |
S1 | 0.80927 (12) | −0.00491 (8) | 0.58078 (7) | 0.0170 (3) | |
S2 | 0.80970 (12) | 0.22695 (8) | 0.66511 (7) | 0.0152 (3) | |
S3 | 0.93968 (12) | 0.22249 (8) | 0.48562 (7) | 0.0150 (2) | |
S4 | 1.16690 (12) | 0.36639 (9) | 0.64742 (8) | 0.0195 (3) | |
C1 | 0.8038 (5) | −0.0362 (3) | 0.4821 (3) | 0.0164 (10) | |
C2 | 0.8652 (5) | −0.0926 (3) | 0.4576 (3) | 0.0198 (11) | |
H2 | 0.9088 | −0.1133 | 0.4946 | 0.024* | |
C3 | 0.8629 (5) | −0.1186 (4) | 0.3795 (3) | 0.0258 (13) | |
H3 | 0.9035 | −0.1576 | 0.3638 | 0.031* | |
C4 | 0.8017 (5) | −0.0874 (4) | 0.3256 (3) | 0.0248 (12) | |
H4 | 0.801 | −0.1045 | 0.2726 | 0.03* | |
C5 | 0.7413 (5) | −0.0317 (3) | 0.3478 (3) | 0.0201 (11) | |
H5 | 0.7021 | −0.0089 | 0.3097 | 0.024* | |
C6 | 0.7370 (4) | −0.0084 (3) | 0.4257 (3) | 0.0150 (10) | |
C7 | 0.5944 (4) | 0.0695 (3) | 0.4247 (3) | 0.0140 (10) | |
C8 | 0.5121 (5) | 0.0234 (3) | 0.3568 (3) | 0.0174 (11) | |
H8A | 0.5406 | 0.0557 | 0.3105 | 0.026* | |
H8B | 0.4293 | 0.0213 | 0.3658 | 0.026* | |
H8C | 0.5125 | −0.037 | 0.3496 | 0.026* | |
C9 | 0.5660 (4) | 0.1424 (3) | 0.4682 (3) | 0.0124 (9) | |
C10 | 0.4964 (5) | 0.1880 (3) | 0.4247 (3) | 0.0163 (10) | |
H10A | 0.5168 | 0.1895 | 0.3705 | 0.024* | |
H10B | 0.5172 | 0.2487 | 0.4466 | 0.024* | |
H10C | 0.4091 | 0.156 | 0.4285 | 0.024* | |
C11 | 0.5911 (5) | 0.2222 (3) | 0.5909 (3) | 0.0133 (10) | |
C12 | 0.4839 (5) | 0.2405 (3) | 0.5919 (3) | 0.0177 (11) | |
H12 | 0.4188 | 0.2096 | 0.556 | 0.021* | |
C13 | 0.4701 (5) | 0.3026 (3) | 0.6440 (3) | 0.0194 (11) | |
H13 | 0.3963 | 0.3143 | 0.6438 | 0.023* | |
C14 | 0.5652 (5) | 0.3482 (3) | 0.6970 (3) | 0.0177 (11) | |
H14 | 0.5583 | 0.3937 | 0.7308 | 0.021* | |
C15 | 0.6695 (5) | 0.3272 (3) | 0.7004 (3) | 0.0169 (11) | |
H15 | 0.7329 | 0.3578 | 0.7375 | 0.02* | |
C16 | 0.6840 (5) | 0.2614 (3) | 0.6501 (3) | 0.0148 (10) | |
C17 | 0.8560 (4) | 0.2667 (3) | 0.4245 (3) | 0.0150 (10) | |
C18 | 0.8134 (4) | 0.2240 (3) | 0.3520 (3) | 0.0159 (10) | |
H18 | 0.8256 | 0.17 | 0.3393 | 0.019* | |
C19 | 0.7545 (5) | 0.2577 (4) | 0.2986 (3) | 0.0201 (11) | |
H19 | 0.7256 | 0.2266 | 0.2502 | 0.024* | |
C20 | 0.7375 (5) | 0.3372 (4) | 0.3155 (3) | 0.0217 (12) | |
H20 | 0.6997 | 0.3618 | 0.2781 | 0.026* | |
C21 | 0.7756 (5) | 0.3799 (4) | 0.3866 (3) | 0.0193 (11) | |
H21 | 0.7638 | 0.4344 | 0.3978 | 0.023* | |
C22 | 0.8316 (4) | 0.3453 (3) | 0.4432 (3) | 0.0136 (10) | |
C23 | 0.8361 (4) | 0.4416 (3) | 0.5533 (3) | 0.0151 (10) | |
C24 | 0.7245 (5) | 0.4620 (4) | 0.5322 (3) | 0.0197 (11) | |
H24A | 0.7461 | 0.5128 | 0.4995 | 0.029* | |
H24B | 0.6895 | 0.4761 | 0.5792 | 0.029* | |
H24C | 0.6649 | 0.4105 | 0.5041 | 0.029* | |
C25 | 0.9080 (4) | 0.4853 (3) | 0.6267 (3) | 0.0147 (10) | |
C26 | 0.9015 (5) | 0.5728 (3) | 0.6539 (3) | 0.0216 (11) | |
H26A | 0.8823 | 0.6025 | 0.6098 | 0.032* | |
H26B | 0.9799 | 0.6099 | 0.6786 | 0.032* | |
H26C | 0.8379 | 0.5633 | 0.6912 | 0.032* | |
C27 | 1.0491 (5) | 0.4672 (3) | 0.7237 (3) | 0.0163 (10) | |
C28 | 1.0337 (5) | 0.5174 (3) | 0.7869 (3) | 0.0224 (12) | |
H28 | 0.9673 | 0.538 | 0.7865 | 0.027* | |
C29 | 1.1155 (5) | 0.5374 (3) | 0.8506 (3) | 0.0230 (12) | |
H29 | 1.1067 | 0.5733 | 0.8929 | 0.028* | |
C30 | 1.2102 (5) | 0.5045 (3) | 0.8521 (3) | 0.0228 (12) | |
H30 | 1.2664 | 0.5187 | 0.8953 | 0.027* | |
C31 | 1.2232 (5) | 0.4513 (3) | 0.7910 (3) | 0.0202 (11) | |
H31 | 1.2866 | 0.4275 | 0.7939 | 0.024* | |
Zn3 | 0.41800 (6) | 0.30363 (4) | 0.16001 (3) | 0.01718 (13) | |
Zn4 | 0.57297 (5) | 0.18855 (4) | 0.07942 (3) | 0.01522 (13) | |
N5 | 0.2625 (4) | 0.2490 (3) | 0.0825 (2) | 0.0175 (9) | |
N6 | 0.2693 (4) | 0.2633 (3) | 0.2340 (2) | 0.0135 (8) | |
N7 | 0.4144 (4) | 0.0818 (3) | 0.0343 (2) | 0.0145 (9) | |
N8 | 0.6096 (4) | 0.1704 (3) | −0.0377 (2) | 0.0155 (9) | |
S5 | 0.53022 (12) | 0.32299 (9) | 0.04626 (7) | 0.0178 (3) | |
S6 | 0.48520 (13) | 0.42718 (9) | 0.24273 (8) | 0.0218 (3) | |
S7 | 0.77557 (12) | 0.20710 (9) | 0.10127 (7) | 0.0172 (3) | |
S8 | 0.46991 (12) | 0.17128 (8) | 0.19587 (7) | 0.0165 (3) | |
C32 | 1.1447 (5) | 0.4317 (3) | 0.7248 (3) | 0.0162 (10) | |
C33 | 0.4037 (5) | 0.2820 (3) | −0.0205 (3) | 0.0165 (10) | |
C34 | 0.4249 (5) | 0.2865 (3) | −0.0992 (3) | 0.0204 (11) | |
H34 | 0.5061 | 0.3052 | −0.1151 | 0.024* | |
C35 | 0.3300 (5) | 0.2642 (3) | −0.1545 (3) | 0.0224 (12) | |
H35 | 0.3463 | 0.2666 | −0.2077 | 0.027* | |
C36 | 0.2114 (5) | 0.2384 (4) | −0.1320 (3) | 0.0253 (12) | |
H36 | 0.1463 | 0.2257 | −0.1696 | 0.03* | |
C37 | 0.1877 (5) | 0.2310 (4) | −0.0542 (3) | 0.0228 (12) | |
H37 | 0.106 | 0.213 | −0.0391 | 0.027* | |
C38 | 0.2821 (5) | 0.2497 (3) | 0.0022 (3) | 0.0170 (11) | |
C39 | 0.1666 (5) | 0.2015 (3) | 0.1152 (3) | 0.0155 (10) | |
C40 | 0.0580 (5) | 0.1277 (4) | 0.0798 (3) | 0.0211 (11) | |
H40A | −0.0076 | 0.1502 | 0.0682 | 0.032* | |
H40B | 0.0305 | 0.0805 | 0.1161 | 0.032* | |
H40C | 0.0803 | 0.1041 | 0.0321 | 0.032* | |
C41 | 0.1642 (5) | 0.2219 (3) | 0.2011 (3) | 0.0161 (10) | |
C42 | 0.0443 (5) | 0.1980 (4) | 0.2372 (3) | 0.0234 (12) | |
H42A | −0.016 | 0.2056 | 0.2005 | 0.035* | |
H42B | 0.052 | 0.2366 | 0.2836 | 0.035* | |
H42C | 0.018 | 0.1362 | 0.2513 | 0.035* | |
C43 | 0.3002 (4) | 0.2968 (3) | 0.3113 (3) | 0.0143 (10) | |
C44 | 0.2396 (5) | 0.2566 (3) | 0.3756 (3) | 0.0167 (10) | |
H44 | 0.1707 | 0.2037 | 0.3689 | 0.02* | |
C45 | 0.2803 (5) | 0.2942 (3) | 0.4486 (3) | 0.0183 (11) | |
H45 | 0.2379 | 0.2677 | 0.4921 | 0.022* | |
C46 | 0.3826 (5) | 0.3701 (3) | 0.4591 (3) | 0.0197 (11) | |
H46 | 0.4101 | 0.3956 | 0.5096 | 0.024* | |
C47 | 0.4440 (5) | 0.4082 (3) | 0.3966 (3) | 0.0183 (11) | |
H47 | 0.5155 | 0.4592 | 0.4045 | 0.022* | |
C48 | 0.4040 (5) | 0.3739 (3) | 0.3211 (3) | 0.0160 (10) | |
C49 | 0.8146 (5) | 0.2436 (3) | 0.0087 (3) | 0.0154 (10) | |
C50 | 0.9351 (5) | 0.2970 (3) | −0.0031 (3) | 0.0188 (11) | |
H50 | 0.9937 | 0.3134 | 0.039 | 0.023* | |
C51 | 0.9688 (5) | 0.3259 (4) | −0.0757 (3) | 0.0230 (12) | |
H51 | 1.0508 | 0.3617 | −0.0829 | 0.028* | |
C52 | 0.8861 (5) | 0.3037 (4) | −0.1378 (3) | 0.0262 (13) | |
H52 | 0.9106 | 0.3243 | −0.1872 | 0.031* | |
C53 | 0.7669 (5) | 0.2512 (4) | −0.1275 (3) | 0.0212 (11) | |
H53 | 0.7096 | 0.2363 | −0.1702 | 0.025* | |
C54 | 0.7292 (5) | 0.2195 (3) | −0.0555 (3) | 0.0185 (11) | |
C55 | 0.5228 (5) | 0.1159 (3) | −0.0802 (3) | 0.0160 (10) | |
C56 | 0.5272 (5) | 0.0860 (4) | −0.1628 (3) | 0.0231 (12) | |
H56A | 0.4988 | 0.1224 | −0.197 | 0.035* | |
H56B | 0.4748 | 0.0239 | −0.1713 | 0.035* | |
H56C | 0.611 | 0.0924 | −0.1739 | 0.035* | |
C57 | 0.4049 (5) | 0.0767 (3) | −0.0401 (3) | 0.0159 (10) | |
C58 | 0.2908 (5) | 0.0402 (3) | −0.0902 (3) | 0.0191 (11) | |
H58A | 0.3007 | 0.0723 | −0.1377 | 0.029* | |
H58B | 0.223 | 0.047 | −0.0627 | 0.029* | |
H58C | 0.274 | −0.0227 | −0.1032 | 0.029* | |
C59 | 0.3217 (5) | 0.0453 (3) | 0.0852 (3) | 0.0145 (10) | |
C60 | 0.2216 (5) | −0.0329 (3) | 0.0670 (3) | 0.0194 (11) | |
H60 | 0.2116 | −0.0603 | 0.0166 | 0.023* | |
C61 | 0.1376 (5) | −0.0706 (4) | 0.1212 (3) | 0.0229 (12) | |
H61 | 0.0707 | −0.1233 | 0.1076 | 0.028* | |
C62 | 0.1506 (5) | −0.0317 (4) | 0.1952 (3) | 0.0250 (12) | |
H62 | 0.0917 | −0.0569 | 0.2318 | 0.03* | |
C63 | 0.2497 (5) | 0.0441 (3) | 0.2157 (3) | 0.0198 (11) | |
H63 | 0.2581 | 0.0706 | 0.2663 | 0.024* | |
C64 | 0.3386 (5) | 0.0823 (3) | 0.1617 (3) | 0.0167 (10) | |
C1B | 0.2468 (16) | 0.4851 (11) | 0.0939 (8) | 0.049 (4) | 0.819 (7) |
H1B1 | 0.1839 | 0.5102 | 0.0821 | 0.073* | 0.819 (7) |
H1B2 | 0.238 | 0.4356 | 0.057 | 0.073* | 0.819 (7) |
H1B3 | 0.3272 | 0.5307 | 0.0903 | 0.073* | 0.819 (7) |
O1B | 0.2346 (7) | 0.4548 (6) | 0.1692 (5) | 0.062 (2) | 0.819 (7) |
H1B | 0.302 (5) | 0.453 (7) | 0.185 (6) | 0.093* | 0.819 (7) |
O1A | 0.172 (2) | 0.3999 (15) | 0.1380 (16) | 0.062 (2) | 0.181 (7) |
S1A | 0.2543 (16) | 0.4906 (12) | 0.1232 (8) | 0.036 (4) | 0.181 (7) |
C1A | 0.357 (3) | 0.469 (2) | 0.0575 (18) | 0.054 (10) | 0.181 (7) |
H1A1 | 0.4382 | 0.4875 | 0.0824 | 0.08* | 0.181 (7) |
H1A2 | 0.3587 | 0.5022 | 0.0112 | 0.08* | 0.181 (7) |
H1A3 | 0.3285 | 0.4056 | 0.043 | 0.08* | 0.181 (7) |
C2A | 0.164 (3) | 0.523 (2) | 0.0528 (16) | 0.054 (10) | 0.181 (7) |
H2A1 | 0.125 | 0.4733 | 0.0154 | 0.08* | 0.181 (7) |
H2A2 | 0.2169 | 0.5735 | 0.026 | 0.08* | 0.181 (7) |
H2A3 | 0.1022 | 0.5398 | 0.0787 | 0.08* | 0.181 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.0144 (3) | 0.0116 (3) | 0.0150 (3) | 0.0040 (2) | 0.0000 (2) | −0.0006 (2) |
Zn2 | 0.0145 (3) | 0.0118 (3) | 0.0176 (3) | 0.0054 (2) | −0.0008 (2) | −0.0017 (2) |
N1 | 0.017 (2) | 0.0089 (19) | 0.0128 (19) | 0.0014 (17) | 0.0025 (16) | 0.0006 (15) |
N2 | 0.012 (2) | 0.0113 (19) | 0.0157 (19) | 0.0052 (17) | 0.0014 (16) | 0.0004 (16) |
N3 | 0.016 (2) | 0.011 (2) | 0.0141 (19) | 0.0043 (17) | 0.0009 (16) | 0.0045 (16) |
N4 | 0.010 (2) | 0.012 (2) | 0.020 (2) | 0.0045 (17) | 0.0024 (16) | −0.0012 (16) |
S1 | 0.0167 (7) | 0.0134 (6) | 0.0217 (6) | 0.0058 (5) | 0.0005 (5) | 0.0031 (5) |
S2 | 0.0169 (7) | 0.0163 (6) | 0.0134 (5) | 0.0069 (5) | 0.0012 (5) | 0.0006 (5) |
S3 | 0.0148 (7) | 0.0150 (6) | 0.0158 (6) | 0.0059 (5) | 0.0014 (5) | −0.0001 (5) |
S4 | 0.0139 (7) | 0.0202 (7) | 0.0247 (7) | 0.0073 (5) | −0.0027 (5) | −0.0050 (5) |
C1 | 0.016 (3) | 0.014 (2) | 0.018 (2) | 0.003 (2) | 0.006 (2) | 0.0001 (19) |
C2 | 0.017 (3) | 0.009 (2) | 0.033 (3) | 0.005 (2) | 0.004 (2) | 0.001 (2) |
C3 | 0.024 (3) | 0.018 (3) | 0.038 (3) | 0.012 (2) | 0.005 (2) | −0.008 (2) |
C4 | 0.024 (3) | 0.025 (3) | 0.026 (3) | 0.011 (3) | 0.002 (2) | −0.009 (2) |
C5 | 0.018 (3) | 0.020 (3) | 0.022 (3) | 0.006 (2) | −0.003 (2) | −0.003 (2) |
C6 | 0.012 (3) | 0.009 (2) | 0.021 (2) | 0.002 (2) | −0.0021 (19) | −0.0062 (19) |
C7 | 0.009 (2) | 0.015 (2) | 0.013 (2) | −0.001 (2) | −0.0011 (18) | −0.0011 (19) |
C8 | 0.014 (3) | 0.020 (3) | 0.016 (2) | 0.004 (2) | −0.0074 (19) | −0.001 (2) |
C9 | 0.009 (2) | 0.008 (2) | 0.019 (2) | −0.0003 (19) | 0.0053 (18) | 0.0038 (18) |
C10 | 0.014 (3) | 0.020 (3) | 0.016 (2) | 0.008 (2) | 0.0009 (19) | 0.000 (2) |
C11 | 0.017 (3) | 0.011 (2) | 0.012 (2) | 0.005 (2) | 0.0014 (18) | 0.0009 (18) |
C12 | 0.018 (3) | 0.016 (3) | 0.018 (2) | 0.006 (2) | 0.003 (2) | −0.001 (2) |
C13 | 0.019 (3) | 0.019 (3) | 0.023 (3) | 0.010 (2) | 0.008 (2) | 0.003 (2) |
C14 | 0.022 (3) | 0.014 (2) | 0.017 (2) | 0.007 (2) | 0.005 (2) | 0.0019 (19) |
C15 | 0.023 (3) | 0.016 (2) | 0.014 (2) | 0.010 (2) | 0.001 (2) | −0.0001 (19) |
C16 | 0.016 (3) | 0.013 (2) | 0.016 (2) | 0.004 (2) | 0.0063 (19) | 0.0015 (19) |
C17 | 0.013 (3) | 0.016 (2) | 0.013 (2) | 0.001 (2) | 0.0028 (18) | 0.0024 (19) |
C18 | 0.009 (2) | 0.017 (3) | 0.020 (2) | 0.002 (2) | 0.0048 (19) | 0.003 (2) |
C19 | 0.010 (3) | 0.031 (3) | 0.016 (2) | 0.003 (2) | 0.0022 (19) | 0.003 (2) |
C20 | 0.015 (3) | 0.028 (3) | 0.020 (3) | 0.003 (2) | 0.003 (2) | 0.013 (2) |
C21 | 0.015 (3) | 0.021 (3) | 0.024 (3) | 0.009 (2) | 0.002 (2) | 0.008 (2) |
C22 | 0.009 (2) | 0.014 (2) | 0.018 (2) | 0.003 (2) | −0.0004 (18) | 0.0037 (19) |
C23 | 0.010 (2) | 0.010 (2) | 0.026 (3) | 0.0034 (19) | 0.004 (2) | 0.0047 (19) |
C24 | 0.013 (3) | 0.023 (3) | 0.029 (3) | 0.012 (2) | 0.009 (2) | 0.005 (2) |
C25 | 0.012 (3) | 0.014 (2) | 0.021 (2) | 0.007 (2) | 0.0095 (19) | 0.0041 (19) |
C26 | 0.023 (3) | 0.017 (3) | 0.024 (3) | 0.006 (2) | 0.003 (2) | 0.000 (2) |
C27 | 0.015 (3) | 0.010 (2) | 0.020 (2) | −0.001 (2) | 0.004 (2) | −0.0004 (19) |
C28 | 0.025 (3) | 0.014 (3) | 0.024 (3) | 0.002 (2) | 0.003 (2) | −0.001 (2) |
C29 | 0.033 (3) | 0.010 (2) | 0.021 (3) | 0.001 (2) | 0.002 (2) | 0.000 (2) |
C30 | 0.019 (3) | 0.015 (3) | 0.024 (3) | −0.008 (2) | −0.004 (2) | 0.003 (2) |
C31 | 0.015 (3) | 0.016 (3) | 0.024 (3) | −0.001 (2) | −0.002 (2) | 0.006 (2) |
Zn3 | 0.0150 (3) | 0.0170 (3) | 0.0166 (3) | 0.0023 (2) | 0.0028 (2) | −0.0039 (2) |
Zn4 | 0.0135 (3) | 0.0171 (3) | 0.0125 (3) | 0.0025 (2) | 0.0006 (2) | −0.0024 (2) |
N5 | 0.017 (2) | 0.019 (2) | 0.018 (2) | 0.0082 (19) | 0.0001 (17) | −0.0036 (17) |
N6 | 0.017 (2) | 0.012 (2) | 0.0143 (19) | 0.0079 (17) | 0.0001 (16) | −0.0009 (16) |
N7 | 0.015 (2) | 0.013 (2) | 0.0140 (19) | 0.0027 (17) | −0.0001 (16) | −0.0010 (16) |
N8 | 0.019 (2) | 0.015 (2) | 0.0122 (19) | 0.0048 (18) | 0.0017 (16) | −0.0024 (16) |
S5 | 0.0155 (7) | 0.0172 (6) | 0.0173 (6) | 0.0017 (5) | 0.0025 (5) | −0.0013 (5) |
S6 | 0.0210 (7) | 0.0156 (6) | 0.0229 (6) | −0.0006 (5) | 0.0055 (5) | −0.0056 (5) |
S7 | 0.0150 (7) | 0.0220 (7) | 0.0135 (6) | 0.0050 (5) | 0.0014 (5) | −0.0004 (5) |
S8 | 0.0156 (7) | 0.0180 (6) | 0.0125 (5) | 0.0019 (5) | 0.0000 (5) | −0.0016 (5) |
C32 | 0.017 (3) | 0.013 (2) | 0.015 (2) | −0.001 (2) | 0.0004 (19) | 0.0005 (19) |
C33 | 0.015 (3) | 0.010 (2) | 0.023 (3) | 0.002 (2) | −0.001 (2) | −0.0027 (19) |
C34 | 0.021 (3) | 0.019 (3) | 0.020 (3) | 0.004 (2) | 0.007 (2) | 0.004 (2) |
C35 | 0.031 (3) | 0.021 (3) | 0.014 (2) | 0.007 (2) | 0.004 (2) | 0.003 (2) |
C36 | 0.031 (3) | 0.021 (3) | 0.021 (3) | 0.005 (3) | −0.005 (2) | −0.002 (2) |
C37 | 0.024 (3) | 0.022 (3) | 0.022 (3) | 0.009 (2) | 0.001 (2) | −0.003 (2) |
C38 | 0.019 (3) | 0.013 (2) | 0.018 (2) | 0.003 (2) | 0.004 (2) | −0.0007 (19) |
C39 | 0.014 (3) | 0.015 (2) | 0.017 (2) | 0.006 (2) | −0.0006 (19) | −0.0038 (19) |
C40 | 0.017 (3) | 0.024 (3) | 0.021 (3) | 0.006 (2) | −0.002 (2) | −0.002 (2) |
C41 | 0.011 (3) | 0.017 (3) | 0.016 (2) | 0.001 (2) | 0.0029 (19) | −0.0003 (19) |
C42 | 0.012 (3) | 0.036 (3) | 0.024 (3) | 0.009 (2) | 0.000 (2) | −0.001 (2) |
C43 | 0.011 (2) | 0.016 (2) | 0.016 (2) | 0.006 (2) | −0.0028 (19) | −0.0050 (19) |
C44 | 0.013 (3) | 0.016 (2) | 0.025 (3) | 0.010 (2) | −0.003 (2) | −0.001 (2) |
C45 | 0.018 (3) | 0.021 (3) | 0.021 (3) | 0.012 (2) | 0.005 (2) | 0.004 (2) |
C46 | 0.025 (3) | 0.018 (3) | 0.019 (2) | 0.013 (2) | −0.004 (2) | −0.004 (2) |
C47 | 0.018 (3) | 0.012 (2) | 0.025 (3) | 0.006 (2) | −0.003 (2) | 0.000 (2) |
C48 | 0.017 (3) | 0.014 (2) | 0.015 (2) | 0.005 (2) | 0.0006 (19) | −0.0073 (19) |
C49 | 0.015 (3) | 0.014 (2) | 0.017 (2) | 0.004 (2) | 0.0038 (19) | −0.0022 (19) |
C50 | 0.019 (3) | 0.018 (3) | 0.019 (2) | 0.005 (2) | 0.002 (2) | 0.001 (2) |
C51 | 0.021 (3) | 0.021 (3) | 0.027 (3) | 0.007 (2) | 0.007 (2) | 0.005 (2) |
C52 | 0.033 (4) | 0.022 (3) | 0.019 (3) | 0.003 (3) | 0.008 (2) | 0.008 (2) |
C53 | 0.025 (3) | 0.021 (3) | 0.019 (3) | 0.010 (2) | −0.001 (2) | 0.003 (2) |
C54 | 0.024 (3) | 0.019 (3) | 0.013 (2) | 0.008 (2) | 0.005 (2) | 0.001 (2) |
C55 | 0.019 (3) | 0.019 (3) | 0.011 (2) | 0.009 (2) | 0.0002 (19) | −0.0015 (19) |
C56 | 0.031 (3) | 0.027 (3) | 0.011 (2) | 0.009 (3) | 0.003 (2) | 0.000 (2) |
C57 | 0.015 (3) | 0.016 (2) | 0.016 (2) | 0.006 (2) | −0.0042 (19) | −0.0026 (19) |
C58 | 0.023 (3) | 0.018 (3) | 0.015 (2) | 0.006 (2) | −0.003 (2) | −0.001 (2) |
C59 | 0.014 (3) | 0.011 (2) | 0.016 (2) | 0.001 (2) | 0.0014 (19) | 0.0016 (18) |
C60 | 0.022 (3) | 0.018 (3) | 0.016 (2) | 0.005 (2) | −0.003 (2) | −0.004 (2) |
C61 | 0.014 (3) | 0.019 (3) | 0.029 (3) | −0.003 (2) | 0.002 (2) | 0.003 (2) |
C62 | 0.019 (3) | 0.020 (3) | 0.033 (3) | 0.001 (2) | 0.004 (2) | 0.007 (2) |
C63 | 0.017 (3) | 0.022 (3) | 0.019 (2) | 0.004 (2) | 0.006 (2) | 0.004 (2) |
C64 | 0.017 (3) | 0.013 (2) | 0.019 (2) | 0.003 (2) | 0.002 (2) | 0.0019 (19) |
C1B | 0.050 (7) | 0.035 (6) | 0.053 (10) | 0.008 (5) | −0.012 (8) | −0.008 (7) |
O1B | 0.052 (5) | 0.115 (7) | 0.043 (4) | 0.055 (5) | 0.019 (3) | 0.036 (4) |
O1A | 0.052 (5) | 0.115 (7) | 0.043 (4) | 0.055 (5) | 0.019 (3) | 0.036 (4) |
S1A | 0.031 (7) | 0.037 (7) | 0.038 (10) | 0.012 (5) | −0.001 (7) | −0.007 (7) |
C1A | 0.09 (3) | 0.08 (2) | 0.025 (13) | 0.07 (2) | 0.012 (14) | 0.022 (14) |
C2A | 0.09 (3) | 0.08 (2) | 0.025 (13) | 0.07 (2) | 0.012 (14) | 0.022 (14) |
Zn1—N1 | 2.128 (4) | Zn4—S7 | 2.3111 (16) |
Zn1—N2 | 2.171 (4) | Zn4—S8 | 2.3689 (15) |
Zn1—S1 | 2.3139 (16) | Zn4—S5 | 2.4773 (17) |
Zn1—S2 | 2.3742 (14) | N5—C39 | 1.286 (6) |
Zn1—S3 | 2.4861 (15) | N5—C38 | 1.423 (6) |
Zn2—N4 | 2.130 (4) | N6—C41 | 1.282 (6) |
Zn2—N3 | 2.151 (4) | N6—C43 | 1.415 (6) |
Zn2—S4 | 2.3027 (16) | N7—C57 | 1.291 (6) |
Zn2—S3 | 2.3922 (15) | N7—C59 | 1.405 (6) |
Zn2—S2 | 2.5011 (15) | N8—C55 | 1.279 (6) |
N1—C7 | 1.278 (6) | N8—C54 | 1.404 (7) |
N1—C6 | 1.410 (6) | S5—C33 | 1.770 (5) |
N2—C9 | 1.299 (6) | S6—C48 | 1.763 (5) |
N2—C11 | 1.422 (6) | S7—C49 | 1.755 (5) |
N3—C23 | 1.298 (6) | S8—C64 | 1.767 (5) |
N3—C22 | 1.412 (6) | C33—C34 | 1.398 (7) |
N4—C25 | 1.284 (6) | C33—C38 | 1.415 (7) |
N4—C27 | 1.412 (6) | C34—C35 | 1.385 (7) |
S1—C1 | 1.761 (5) | C34—H34 | 0.95 |
S2—C16 | 1.766 (5) | C35—C36 | 1.383 (8) |
S3—C17 | 1.756 (5) | C35—H35 | 0.95 |
S4—C32 | 1.759 (5) | C36—C37 | 1.391 (7) |
C1—C2 | 1.406 (7) | C36—H36 | 0.95 |
C1—C6 | 1.419 (7) | C37—C38 | 1.398 (7) |
C2—C3 | 1.402 (7) | C37—H37 | 0.95 |
C2—H2 | 0.95 | C39—C40 | 1.502 (7) |
C3—C4 | 1.377 (8) | C39—C41 | 1.519 (6) |
C3—H3 | 0.95 | C40—H40A | 0.98 |
C4—C5 | 1.378 (7) | C40—H40B | 0.98 |
C4—H4 | 0.95 | C40—H40C | 0.98 |
C5—C6 | 1.397 (7) | C41—C42 | 1.493 (7) |
C5—H5 | 0.95 | C42—H42A | 0.98 |
C7—C8 | 1.496 (6) | C42—H42B | 0.98 |
C7—C9 | 1.512 (6) | C42—H42C | 0.98 |
C8—H8A | 0.98 | C43—C44 | 1.401 (7) |
C8—H8B | 0.98 | C43—C48 | 1.406 (7) |
C8—H8C | 0.98 | C44—C45 | 1.381 (7) |
C9—C10 | 1.486 (7) | C44—H44 | 0.95 |
C10—H10A | 0.98 | C45—C46 | 1.386 (7) |
C10—H10B | 0.98 | C45—H45 | 0.95 |
C10—H10C | 0.98 | C46—C47 | 1.370 (7) |
C11—C12 | 1.393 (7) | C46—H46 | 0.95 |
C11—C16 | 1.430 (7) | C47—C48 | 1.403 (7) |
C12—C13 | 1.379 (6) | C47—H47 | 0.95 |
C12—H12 | 0.95 | C49—C50 | 1.405 (7) |
C13—C14 | 1.394 (7) | C49—C54 | 1.422 (7) |
C13—H13 | 0.95 | C50—C51 | 1.385 (7) |
C14—C15 | 1.382 (7) | C50—H50 | 0.95 |
C14—H14 | 0.95 | C51—C52 | 1.376 (8) |
C15—C16 | 1.408 (6) | C51—H51 | 0.95 |
C15—H15 | 0.95 | C52—C53 | 1.383 (8) |
C17—C18 | 1.401 (6) | C52—H52 | 0.95 |
C17—C22 | 1.423 (7) | C53—C54 | 1.396 (7) |
C18—C19 | 1.379 (7) | C53—H53 | 0.95 |
C18—H18 | 0.95 | C55—C56 | 1.503 (6) |
C19—C20 | 1.387 (8) | C55—C57 | 1.515 (7) |
C19—H19 | 0.95 | C56—H56A | 0.98 |
C20—C21 | 1.373 (7) | C56—H56B | 0.98 |
C20—H20 | 0.95 | C56—H56C | 0.98 |
C21—C22 | 1.404 (7) | C57—C58 | 1.495 (7) |
C21—H21 | 0.95 | C58—H58A | 0.98 |
C23—C24 | 1.498 (7) | C58—H58B | 0.98 |
C23—C25 | 1.510 (7) | C58—H58C | 0.98 |
C24—H24A | 0.98 | C59—C60 | 1.409 (7) |
C24—H24B | 0.98 | C59—C64 | 1.414 (6) |
C24—H24C | 0.98 | C60—C61 | 1.386 (7) |
C25—C26 | 1.501 (6) | C60—H60 | 0.95 |
C26—H26A | 0.98 | C61—C62 | 1.389 (7) |
C26—H26B | 0.98 | C61—H61 | 0.95 |
C26—H26C | 0.98 | C62—C63 | 1.387 (7) |
C27—C28 | 1.393 (7) | C62—H62 | 0.95 |
C27—C32 | 1.428 (7) | C63—C64 | 1.419 (7) |
C28—C29 | 1.393 (8) | C63—H63 | 0.95 |
C28—H28 | 0.95 | C1B—O1B | 1.408 (14) |
C29—C30 | 1.390 (8) | C1B—H1B1 | 0.98 |
C29—H29 | 0.95 | C1B—H1B2 | 0.98 |
C30—C31 | 1.386 (7) | C1B—H1B3 | 0.98 |
C30—H30 | 0.95 | O1B—H1B | 0.850 (15) |
C31—C32 | 1.404 (7) | O1A—S1A | 1.484 (10) |
C31—H31 | 0.95 | S1A—C1A | 1.795 (10) |
Zn3—N5 | 2.134 (4) | S1A—C2A | 1.799 (10) |
Zn3—N6 | 2.134 (4) | C1A—H1A1 | 0.98 |
Zn3—S6 | 2.2952 (15) | C1A—H1A2 | 0.98 |
Zn3—S5 | 2.3831 (15) | C1A—H1A3 | 0.98 |
Zn3—S8 | 2.5133 (17) | C2A—H2A1 | 0.98 |
Zn4—N8 | 2.125 (4) | C2A—H2A2 | 0.98 |
Zn4—N7 | 2.148 (4) | C2A—H2A3 | 0.98 |
N1—Zn1—N2 | 74.85 (15) | N7—Zn4—S8 | 84.74 (11) |
N1—Zn1—S1 | 83.74 (12) | S7—Zn4—S8 | 111.50 (5) |
N2—Zn1—S1 | 136.24 (11) | N8—Zn4—S5 | 89.08 (12) |
N1—Zn1—S2 | 157.93 (12) | N7—Zn4—S5 | 103.73 (12) |
N2—Zn1—S2 | 83.41 (11) | S7—Zn4—S5 | 115.80 (5) |
S1—Zn1—S2 | 115.47 (5) | S8—Zn4—S5 | 94.51 (5) |
N1—Zn1—S3 | 90.45 (11) | C39—N5—C38 | 126.7 (4) |
N2—Zn1—S3 | 108.88 (11) | C39—N5—Zn3 | 113.6 (3) |
S1—Zn1—S3 | 109.00 (5) | C38—N5—Zn3 | 117.5 (3) |
S2—Zn1—S3 | 93.03 (5) | C41—N6—C43 | 129.3 (4) |
N4—Zn2—N3 | 76.04 (16) | C41—N6—Zn3 | 116.2 (3) |
N4—Zn2—S4 | 84.31 (12) | C43—N6—Zn3 | 113.8 (3) |
N3—Zn2—S4 | 137.85 (12) | C57—N7—C59 | 127.3 (4) |
N4—Zn2—S3 | 159.75 (12) | C57—N7—Zn4 | 112.7 (3) |
N3—Zn2—S3 | 83.72 (11) | C59—N7—Zn4 | 117.3 (3) |
S4—Zn2—S3 | 111.68 (5) | C55—N8—C54 | 130.0 (4) |
N4—Zn2—S2 | 92.08 (12) | C55—N8—Zn4 | 116.5 (3) |
N3—Zn2—S2 | 103.25 (12) | C54—N8—Zn4 | 113.4 (3) |
S4—Zn2—S2 | 114.53 (6) | C33—S5—Zn3 | 96.89 (17) |
S3—Zn2—S2 | 92.22 (5) | C33—S5—Zn4 | 103.54 (17) |
C7—N1—C6 | 128.5 (4) | Zn3—S5—Zn4 | 86.33 (5) |
C7—N1—Zn1 | 117.7 (3) | C48—S6—Zn3 | 94.82 (16) |
C6—N1—Zn1 | 113.8 (3) | C49—S7—Zn4 | 93.55 (18) |
C9—N2—C11 | 123.9 (4) | C64—S8—Zn4 | 96.85 (17) |
C9—N2—Zn1 | 113.4 (3) | C64—S8—Zn3 | 102.24 (18) |
C11—N2—Zn1 | 118.7 (3) | Zn4—S8—Zn3 | 85.82 (5) |
C23—N3—C22 | 125.1 (4) | C31—C32—C27 | 117.4 (5) |
C23—N3—Zn2 | 112.1 (3) | C31—C32—S4 | 119.9 (4) |
C22—N3—Zn2 | 118.8 (3) | C27—C32—S4 | 122.7 (4) |
C25—N4—C27 | 128.0 (4) | C34—C33—C38 | 118.6 (5) |
C25—N4—Zn2 | 116.0 (3) | C34—C33—S5 | 118.3 (4) |
C27—N4—Zn2 | 115.5 (3) | C38—C33—S5 | 123.0 (4) |
C1—S1—Zn1 | 93.75 (18) | C35—C34—C33 | 121.5 (5) |
C16—S2—Zn1 | 98.49 (16) | C35—C34—H34 | 119.3 |
C16—S2—Zn2 | 104.77 (17) | C33—C34—H34 | 119.3 |
Zn1—S2—Zn2 | 87.36 (5) | C36—C35—C34 | 119.8 (5) |
C17—S3—Zn2 | 97.14 (17) | C36—C35—H35 | 120.1 |
C17—S3—Zn1 | 99.37 (17) | C34—C35—H35 | 120.1 |
Zn2—S3—Zn1 | 87.31 (5) | C35—C36—C37 | 119.9 (5) |
C32—S4—Zn2 | 95.79 (18) | C35—C36—H36 | 120.1 |
C2—C1—C6 | 118.0 (4) | C37—C36—H36 | 120.1 |
C2—C1—S1 | 119.5 (4) | C36—C37—C38 | 121.0 (5) |
C6—C1—S1 | 122.5 (4) | C36—C37—H37 | 119.5 |
C3—C2—C1 | 121.0 (5) | C38—C37—H37 | 119.5 |
C3—C2—H2 | 119.5 | C37—C38—C33 | 119.0 (5) |
C1—C2—H2 | 119.5 | C37—C38—N5 | 122.7 (5) |
C4—C3—C2 | 119.7 (5) | C33—C38—N5 | 117.7 (4) |
C4—C3—H3 | 120.1 | N5—C39—C40 | 128.5 (4) |
C2—C3—H3 | 120.1 | N5—C39—C41 | 115.5 (4) |
C3—C4—C5 | 120.6 (5) | C40—C39—C41 | 116.0 (4) |
C3—C4—H4 | 119.7 | C39—C40—H40A | 109.5 |
C5—C4—H4 | 119.7 | C39—C40—H40B | 109.5 |
C4—C5—C6 | 120.7 (5) | H40A—C40—H40B | 109.5 |
C4—C5—H5 | 119.6 | C39—C40—H40C | 109.5 |
C6—C5—H5 | 119.6 | H40A—C40—H40C | 109.5 |
C5—C6—N1 | 124.6 (5) | H40B—C40—H40C | 109.5 |
C5—C6—C1 | 119.8 (4) | N6—C41—C42 | 127.0 (4) |
N1—C6—C1 | 114.9 (4) | N6—C41—C39 | 114.1 (4) |
N1—C7—C8 | 128.0 (4) | C42—C41—C39 | 118.8 (4) |
N1—C7—C9 | 114.5 (4) | C41—C42—H42A | 109.5 |
C8—C7—C9 | 117.5 (4) | C41—C42—H42B | 109.5 |
C7—C8—H8A | 109.5 | H42A—C42—H42B | 109.5 |
C7—C8—H8B | 109.5 | C41—C42—H42C | 109.5 |
H8A—C8—H8B | 109.5 | H42A—C42—H42C | 109.5 |
C7—C8—H8C | 109.5 | H42B—C42—H42C | 109.5 |
H8A—C8—H8C | 109.5 | C44—C43—C48 | 120.3 (4) |
H8B—C8—H8C | 109.5 | C44—C43—N6 | 124.9 (4) |
N2—C9—C10 | 128.5 (4) | C48—C43—N6 | 114.7 (4) |
N2—C9—C7 | 114.5 (4) | C45—C44—C43 | 119.8 (5) |
C10—C9—C7 | 116.9 (4) | C45—C44—H44 | 120.1 |
C9—C10—H10A | 109.5 | C43—C44—H44 | 120.1 |
C9—C10—H10B | 109.5 | C44—C45—C46 | 120.5 (5) |
H10A—C10—H10B | 109.5 | C44—C45—H45 | 119.7 |
C9—C10—H10C | 109.5 | C46—C45—H45 | 119.7 |
H10A—C10—H10C | 109.5 | C47—C46—C45 | 119.9 (5) |
H10B—C10—H10C | 109.5 | C47—C46—H46 | 120.1 |
C12—C11—N2 | 124.1 (4) | C45—C46—H46 | 120.1 |
C12—C11—C16 | 119.4 (4) | C46—C47—C48 | 121.6 (5) |
N2—C11—C16 | 116.2 (4) | C46—C47—H47 | 119.2 |
C13—C12—C11 | 121.4 (5) | C48—C47—H47 | 119.2 |
C13—C12—H12 | 119.3 | C47—C48—C43 | 117.9 (5) |
C11—C12—H12 | 119.3 | C47—C48—S6 | 119.6 (4) |
C12—C13—C14 | 119.6 (5) | C43—C48—S6 | 122.5 (4) |
C12—C13—H13 | 120.2 | C50—C49—C54 | 118.5 (5) |
C14—C13—H13 | 120.2 | C50—C49—S7 | 119.0 (4) |
C15—C14—C13 | 120.0 (5) | C54—C49—S7 | 122.5 (4) |
C15—C14—H14 | 120 | C51—C50—C49 | 120.3 (5) |
C13—C14—H14 | 120 | C51—C50—H50 | 119.9 |
C14—C15—C16 | 121.6 (5) | C49—C50—H50 | 119.9 |
C14—C15—H15 | 119.2 | C52—C51—C50 | 121.3 (5) |
C16—C15—H15 | 119.2 | C52—C51—H51 | 119.3 |
C15—C16—C11 | 117.4 (5) | C50—C51—H51 | 119.3 |
C15—C16—S2 | 119.6 (4) | C51—C52—C53 | 119.4 (5) |
C11—C16—S2 | 122.9 (4) | C51—C52—H52 | 120.3 |
C18—C17—C22 | 117.6 (5) | C53—C52—H52 | 120.3 |
C18—C17—S3 | 118.5 (4) | C52—C53—C54 | 121.2 (5) |
C22—C17—S3 | 124.0 (4) | C52—C53—H53 | 119.4 |
C19—C18—C17 | 122.1 (5) | C54—C53—H53 | 119.4 |
C19—C18—H18 | 118.9 | C53—C54—N8 | 125.9 (5) |
C17—C18—H18 | 118.9 | C53—C54—C49 | 119.3 (5) |
C18—C19—C20 | 119.9 (5) | N8—C54—C49 | 114.7 (4) |
C18—C19—H19 | 120 | N8—C55—C56 | 127.3 (5) |
C20—C19—H19 | 120 | N8—C55—C57 | 114.4 (4) |
C21—C20—C19 | 119.6 (5) | C56—C55—C57 | 118.3 (4) |
C21—C20—H20 | 120.2 | C55—C56—H56A | 109.5 |
C19—C20—H20 | 120.2 | C55—C56—H56B | 109.5 |
C20—C21—C22 | 121.7 (5) | H56A—C56—H56B | 109.5 |
C20—C21—H21 | 119.2 | C55—C56—H56C | 109.5 |
C22—C21—H21 | 119.2 | H56A—C56—H56C | 109.5 |
C21—C22—N3 | 124.3 (4) | H56B—C56—H56C | 109.5 |
C21—C22—C17 | 119.0 (4) | N7—C57—C58 | 127.3 (5) |
N3—C22—C17 | 116.4 (4) | N7—C57—C55 | 115.7 (4) |
N3—C23—C24 | 127.0 (5) | C58—C57—C55 | 117.0 (4) |
N3—C23—C25 | 115.1 (4) | C57—C58—H58A | 109.5 |
C24—C23—C25 | 117.9 (4) | C57—C58—H58B | 109.5 |
C23—C24—H24A | 109.5 | H58A—C58—H58B | 109.5 |
C23—C24—H24B | 109.5 | C57—C58—H58C | 109.5 |
H24A—C24—H24B | 109.5 | H58A—C58—H58C | 109.5 |
C23—C24—H24C | 109.5 | H58B—C58—H58C | 109.5 |
H24A—C24—H24C | 109.5 | N7—C59—C60 | 123.2 (4) |
H24B—C24—H24C | 109.5 | N7—C59—C64 | 117.8 (4) |
N4—C25—C26 | 128.1 (5) | C60—C59—C64 | 118.5 (4) |
N4—C25—C23 | 114.4 (4) | C61—C60—C59 | 121.2 (5) |
C26—C25—C23 | 117.4 (4) | C61—C60—H60 | 119.4 |
C25—C26—H26A | 109.5 | C59—C60—H60 | 119.4 |
C25—C26—H26B | 109.5 | C60—C61—C62 | 120.3 (5) |
H26A—C26—H26B | 109.5 | C60—C61—H61 | 119.9 |
C25—C26—H26C | 109.5 | C62—C61—H61 | 119.9 |
H26A—C26—H26C | 109.5 | C63—C62—C61 | 120.0 (5) |
H26B—C26—H26C | 109.5 | C63—C62—H62 | 120 |
C28—C27—N4 | 124.4 (5) | C61—C62—H62 | 120 |
C28—C27—C32 | 120.7 (5) | C62—C63—C64 | 120.6 (5) |
N4—C27—C32 | 114.8 (4) | C62—C63—H63 | 119.7 |
C27—C28—C29 | 120.1 (5) | C64—C63—H63 | 119.7 |
C27—C28—H28 | 119.9 | C59—C64—C63 | 119.2 (5) |
C29—C28—H28 | 119.9 | C59—C64—S8 | 123.3 (4) |
C30—C29—C28 | 119.8 (5) | C63—C64—S8 | 117.4 (4) |
C30—C29—H29 | 120.1 | O1B—C1B—H1B1 | 109.5 |
C28—C29—H29 | 120.1 | O1B—C1B—H1B2 | 109.5 |
C31—C30—C29 | 120.6 (5) | H1B1—C1B—H1B2 | 109.5 |
C31—C30—H30 | 119.7 | O1B—C1B—H1B3 | 109.5 |
C29—C30—H30 | 119.7 | H1B1—C1B—H1B3 | 109.5 |
C30—C31—C32 | 121.3 (5) | H1B2—C1B—H1B3 | 109.5 |
C30—C31—H31 | 119.3 | C1B—O1B—H1B | 108 (7) |
C32—C31—H31 | 119.3 | O1A—S1A—C1A | 101.9 (8) |
N5—Zn3—N6 | 76.04 (16) | O1A—S1A—C2A | 101.5 (8) |
N5—Zn3—S6 | 133.08 (12) | C1A—S1A—C2A | 96.9 (19) |
N6—Zn3—S6 | 83.58 (11) | S1A—C1A—H1A1 | 109.5 |
N5—Zn3—S5 | 84.75 (12) | S1A—C1A—H1A2 | 109.5 |
N6—Zn3—S5 | 160.63 (11) | H1A1—C1A—H1A2 | 109.5 |
S6—Zn3—S5 | 112.05 (5) | S1A—C1A—H1A3 | 109.5 |
N5—Zn3—S8 | 103.73 (12) | H1A1—C1A—H1A3 | 109.5 |
N6—Zn3—S8 | 88.98 (11) | H1A2—C1A—H1A3 | 109.5 |
S6—Zn3—S8 | 117.84 (6) | S1A—C2A—H2A1 | 109.5 |
S5—Zn3—S8 | 93.23 (5) | S1A—C2A—H2A2 | 109.5 |
N8—Zn4—N7 | 76.02 (16) | H2A1—C2A—H2A2 | 109.5 |
N8—Zn4—S7 | 83.59 (12) | S1A—C2A—H2A3 | 109.5 |
N7—Zn4—S7 | 134.94 (12) | H2A1—C2A—H2A3 | 109.5 |
N8—Zn4—S8 | 160.73 (12) | H2A2—C2A—H2A3 | 109.5 |
Zn1—S1—C1—C2 | 155.8 (4) | Zn3—S5—C33—C34 | 175.2 (4) |
Zn1—S1—C1—C6 | −25.7 (4) | Zn4—S5—C33—C34 | −96.9 (4) |
C6—C1—C2—C3 | 1.6 (8) | Zn3—S5—C33—C38 | −1.1 (4) |
S1—C1—C2—C3 | −179.8 (4) | Zn4—S5—C33—C38 | 86.7 (4) |
C1—C2—C3—C4 | 1.2 (8) | C38—C33—C34—C35 | 3.2 (8) |
C2—C3—C4—C5 | −0.8 (9) | S5—C33—C34—C35 | −173.3 (4) |
C3—C4—C5—C6 | −2.4 (9) | C33—C34—C35—C36 | 1.2 (8) |
C4—C5—C6—N1 | 175.0 (5) | C34—C35—C36—C37 | −2.9 (8) |
C4—C5—C6—C1 | 5.2 (8) | C35—C36—C37—C38 | 0.3 (8) |
C7—N1—C6—C5 | 33.0 (8) | C36—C37—C38—C33 | 4.1 (8) |
Zn1—N1—C6—C5 | −148.8 (4) | C36—C37—C38—N5 | 175.5 (5) |
C7—N1—C6—C1 | −156.8 (5) | C34—C33—C38—C37 | −5.7 (7) |
Zn1—N1—C6—C1 | 21.4 (5) | S5—C33—C38—C37 | 170.6 (4) |
C2—C1—C6—C5 | −4.7 (7) | C34—C33—C38—N5 | −177.6 (5) |
S1—C1—C6—C5 | 176.7 (4) | S5—C33—C38—N5 | −1.3 (7) |
C2—C1—C6—N1 | −175.5 (4) | C39—N5—C38—C37 | 29.5 (8) |
S1—C1—C6—N1 | 6.0 (6) | Zn3—N5—C38—C37 | −168.1 (4) |
C6—N1—C7—C8 | 4.6 (9) | C39—N5—C38—C33 | −159.0 (5) |
Zn1—N1—C7—C8 | −173.6 (4) | Zn3—N5—C38—C33 | 3.4 (6) |
C6—N1—C7—C9 | −178.0 (4) | C38—N5—C39—C40 | 8.2 (9) |
Zn1—N1—C7—C9 | 3.8 (5) | Zn3—N5—C39—C40 | −154.9 (4) |
C11—N2—C9—C10 | 5.8 (8) | C38—N5—C39—C41 | −173.1 (5) |
Zn1—N2—C9—C10 | −151.6 (4) | Zn3—N5—C39—C41 | 23.9 (5) |
C11—N2—C9—C7 | −177.2 (4) | C43—N6—C41—C42 | 0.0 (9) |
Zn1—N2—C9—C7 | 25.4 (5) | Zn3—N6—C41—C42 | −170.6 (4) |
N1—C7—C9—N2 | −20.0 (6) | C43—N6—C41—C39 | 176.1 (4) |
C8—C7—C9—N2 | 157.7 (4) | Zn3—N6—C41—C39 | 5.4 (6) |
N1—C7—C9—C10 | 157.4 (4) | N5—C39—C41—N6 | −20.0 (7) |
C8—C7—C9—C10 | −24.9 (6) | C40—C39—C41—N6 | 158.9 (5) |
C9—N2—C11—C12 | 33.9 (7) | N5—C39—C41—C42 | 156.4 (5) |
Zn1—N2—C11—C12 | −169.8 (4) | C40—C39—C41—C42 | −24.7 (7) |
C9—N2—C11—C16 | −152.6 (5) | C41—N6—C43—C44 | 35.5 (8) |
Zn1—N2—C11—C16 | 3.7 (6) | Zn3—N6—C43—C44 | −153.7 (4) |
N2—C11—C12—C13 | −180.0 (5) | C41—N6—C43—C48 | −148.0 (5) |
C16—C11—C12—C13 | 6.7 (8) | Zn3—N6—C43—C48 | 22.8 (5) |
C11—C12—C13—C14 | −0.1 (8) | C48—C43—C44—C45 | 1.6 (7) |
C12—C13—C14—C15 | −4.1 (8) | N6—C43—C44—C45 | 178.0 (4) |
C13—C14—C15—C16 | 1.4 (8) | C43—C44—C45—C46 | −1.7 (7) |
C14—C15—C16—C11 | 5.2 (7) | C44—C45—C46—C47 | −0.1 (8) |
C14—C15—C16—S2 | −171.6 (4) | C45—C46—C47—C48 | 1.9 (8) |
C12—C11—C16—C15 | −9.1 (7) | C46—C47—C48—C43 | −1.9 (8) |
N2—C11—C16—C15 | 177.1 (4) | C46—C47—C48—S6 | 178.8 (4) |
C12—C11—C16—S2 | 167.6 (4) | C44—C43—C48—C47 | 0.1 (7) |
N2—C11—C16—S2 | −6.2 (6) | N6—C43—C48—C47 | −176.6 (4) |
Zn1—S2—C16—C15 | −178.3 (4) | C44—C43—C48—S6 | 179.4 (4) |
Zn2—S2—C16—C15 | −88.8 (4) | N6—C43—C48—S6 | 2.7 (6) |
Zn1—S2—C16—C11 | 5.1 (4) | Zn3—S6—C48—C47 | 156.4 (4) |
Zn2—S2—C16—C11 | 94.6 (4) | Zn3—S6—C48—C43 | −22.9 (4) |
Zn2—S3—C17—C18 | −180.0 (4) | Zn4—S7—C49—C50 | 155.6 (4) |
Zn1—S3—C17—C18 | −91.5 (4) | Zn4—S7—C49—C54 | −25.8 (4) |
Zn2—S3—C17—C22 | 2.0 (4) | C54—C49—C50—C51 | 0.5 (7) |
Zn1—S3—C17—C22 | 90.5 (4) | S7—C49—C50—C51 | 179.2 (4) |
C22—C17—C18—C19 | 2.7 (7) | C49—C50—C51—C52 | 0.3 (8) |
S3—C17—C18—C19 | −175.4 (4) | C50—C51—C52—C53 | −0.3 (8) |
C17—C18—C19—C20 | 1.0 (8) | C51—C52—C53—C54 | −0.6 (8) |
C18—C19—C20—C21 | −2.4 (8) | C52—C53—C54—N8 | 176.0 (5) |
C19—C20—C21—C22 | −0.1 (8) | C52—C53—C54—C49 | 1.5 (8) |
C20—C21—C22—N3 | 176.9 (5) | C55—N8—C54—C53 | 30.6 (9) |
C20—C21—C22—C17 | 3.9 (8) | Zn4—N8—C54—C53 | −151.5 (4) |
C23—N3—C22—C21 | 29.6 (8) | C55—N8—C54—C49 | −154.7 (5) |
Zn2—N3—C22—C21 | −174.7 (4) | Zn4—N8—C54—C49 | 23.2 (5) |
C23—N3—C22—C17 | −157.3 (5) | C50—C49—C54—C53 | −1.4 (7) |
Zn2—N3—C22—C17 | −1.6 (6) | S7—C49—C54—C53 | 180.0 (4) |
C18—C17—C22—C21 | −5.1 (7) | C50—C49—C54—N8 | −176.5 (4) |
S3—C17—C22—C21 | 172.9 (4) | S7—C49—C54—N8 | 4.9 (6) |
C18—C17—C22—N3 | −178.6 (4) | C54—N8—C55—C56 | 2.7 (9) |
S3—C17—C22—N3 | −0.6 (6) | Zn4—N8—C55—C56 | −175.1 (4) |
C22—N3—C23—C24 | 6.8 (8) | C54—N8—C55—C57 | −179.1 (5) |
Zn2—N3—C23—C24 | −150.3 (4) | Zn4—N8—C55—C57 | 3.1 (6) |
C22—N3—C23—C25 | −174.8 (4) | C59—N7—C57—C58 | 7.9 (8) |
Zn2—N3—C23—C25 | 28.1 (5) | Zn4—N7—C57—C58 | −152.6 (4) |
C27—N4—C25—C26 | 0.0 (8) | C59—N7—C57—C55 | −174.9 (4) |
Zn2—N4—C25—C26 | −171.2 (4) | Zn4—N7—C57—C55 | 24.6 (5) |
C27—N4—C25—C23 | 177.9 (4) | N8—C55—C57—N7 | −19.1 (7) |
Zn2—N4—C25—C23 | 6.7 (5) | C56—C55—C57—N7 | 159.2 (5) |
N3—C23—C25—N4 | −24.0 (6) | N8—C55—C57—C58 | 158.4 (5) |
C24—C23—C25—N4 | 154.5 (5) | C56—C55—C57—C58 | −23.3 (7) |
N3—C23—C25—C26 | 154.1 (5) | C57—N7—C59—C60 | 30.2 (8) |
C24—C23—C25—C26 | −27.3 (6) | Zn4—N7—C59—C60 | −170.2 (4) |
C25—N4—C27—C28 | 31.0 (8) | C57—N7—C59—C64 | −158.6 (5) |
Zn2—N4—C27—C28 | −157.7 (4) | Zn4—N7—C59—C64 | 1.0 (6) |
C25—N4—C27—C32 | −152.9 (5) | N7—C59—C60—C61 | 174.6 (5) |
Zn2—N4—C27—C32 | 18.4 (5) | C64—C59—C60—C61 | 3.4 (8) |
N4—C27—C28—C29 | 179.2 (5) | C59—C60—C61—C62 | −0.1 (9) |
C32—C27—C28—C29 | 3.3 (8) | C60—C61—C62—C63 | −1.5 (9) |
C27—C28—C29—C30 | −2.2 (8) | C61—C62—C63—C64 | −0.3 (8) |
C28—C29—C30—C31 | −0.6 (8) | N7—C59—C64—C63 | −176.8 (5) |
C29—C30—C31—C32 | 2.5 (8) | C60—C59—C64—C63 | −5.1 (8) |
C30—C31—C32—C27 | −1.4 (7) | N7—C59—C64—S8 | −0.2 (7) |
C30—C31—C32—S4 | 178.2 (4) | C60—C59—C64—S8 | 171.5 (4) |
C28—C27—C32—C31 | −1.5 (7) | C62—C63—C64—C59 | 3.6 (8) |
N4—C27—C32—C31 | −177.8 (4) | C62—C63—C64—S8 | −173.2 (4) |
C28—C27—C32—S4 | 178.9 (4) | Zn4—S8—C64—C59 | −0.6 (5) |
N4—C27—C32—S4 | 2.7 (6) | Zn3—S8—C64—C59 | 86.6 (4) |
Zn2—S4—C32—C31 | 161.6 (4) | Zn4—S8—C64—C63 | 176.0 (4) |
Zn2—S4—C32—C27 | −18.9 (4) | Zn3—S8—C64—C63 | −96.8 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1B—H1B···S6 | 0.850 (15) | 2.507 (10) | 3.350 (7) | 172 (9) |
C26—H26C···O1Bi | 0.98 | 2.59 | 3.484 (9) | 151 |
C28—H28···O1Bi | 0.95 | 2.56 | 3.444 (9) | 155 |
C28—H28···O1Ai | 0.95 | 2.57 | 3.42 (3) | 149 |
C50—H50···O1Aii | 0.95 | 2.62 | 3.54 (3) | 165 |
C28—H28···S1Ai | 0.95 | 2.99 | 3.740 (18) | 137 |
C8—H8B···S1iii | 0.98 | 2.91 | 3.880 (5) | 170 |
C10—H10C···S1iii | 0.98 | 2.85 | 3.768 (5) | 156 |
C63—H63···S1iii | 0.95 | 2.93 | 3.663 (5) | 135 |
C2—H2···S3iv | 0.95 | 2.93 | 3.742 (6) | 144 |
C42—H42A···S7v | 0.98 | 2.96 | 3.929 (6) | 172 |
C58—H58C···S7vi | 0.98 | 2.83 | 3.787 (5) | 166 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, y, z; (iii) −x+1, −y, −z+1; (iv) −x+2, −y, −z+1; (v) x−1, y, z; (vi) −x+1, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | [Zn2(C16H14N2S2)2]2·0.18C2H6OS·0.82CH4O |
Mr | 1495.4 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 100 |
a, b, c (Å) | 11.757 (4), 16.145 (6), 17.376 (6) |
α, β, γ (°) | 92.254 (5), 91.897 (6), 110.427 (5) |
V (Å3) | 3084.6 (19) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.87 |
Crystal size (mm) | 0.25 × 0.23 × 0.01 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2008) |
Tmin, Tmax | 0.654, 0.746 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 37532, 15164, 10524 |
Rint | 0.067 |
(sin θ/λ)max (Å−1) | 0.669 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.066, 0.116, 1.11 |
No. of reflections | 15164 |
No. of parameters | 814 |
No. of restraints | 7 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
w = 1/[σ2(Fo2) + 12.0817P] where P = (Fo2 + 2Fc2)/3 | |
Δρmax, Δρmin (e Å−3) | 0.73, −0.81 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SADABS (Bruker, 2008), SIR97 (Altomare et al., 1999), SHELXL-2013 (Sheldrick, 2013), ORTEP-3 for Windows (Farrugia, 2012), WinGX (Farrugia, 2012).
Zn1—N1 | 2.128 (4) | Zn3—N5 | 2.134 (4) |
Zn1—N2 | 2.171 (4) | Zn3—N6 | 2.134 (4) |
Zn1—S1 | 2.3139 (16) | Zn3—S6 | 2.2952 (15) |
Zn1—S2 | 2.3742 (14) | Zn3—S5 | 2.3831 (15) |
Zn1—S3 | 2.4861 (15) | Zn3—S8 | 2.5133 (17) |
Zn2—N4 | 2.130 (4) | Zn4—N8 | 2.125 (4) |
Zn2—N3 | 2.151 (4) | Zn4—N7 | 2.148 (4) |
Zn2—S4 | 2.3027 (16) | Zn4—S7 | 2.3111 (16) |
Zn2—S3 | 2.3922 (15) | Zn4—S8 | 2.3689 (15) |
Zn2—S2 | 2.5011 (15) | Zn4—S5 | 2.4773 (17) |
N1—Zn1—N2 | 74.85 (15) | N5—Zn3—N6 | 76.04 (16) |
N1—Zn1—S1 | 83.74 (12) | N5—Zn3—S6 | 133.08 (12) |
N2—Zn1—S1 | 136.24 (11) | N6—Zn3—S6 | 83.58 (11) |
N1—Zn1—S2 | 157.93 (12) | N5—Zn3—S5 | 84.75 (12) |
N2—Zn1—S2 | 83.41 (11) | N6—Zn3—S5 | 160.63 (11) |
S1—Zn1—S2 | 115.47 (5) | S6—Zn3—S5 | 112.05 (5) |
N1—Zn1—S3 | 90.45 (11) | N5—Zn3—S8 | 103.73 (12) |
N2—Zn1—S3 | 108.88 (11) | N6—Zn3—S8 | 88.98 (11) |
S1—Zn1—S3 | 109.00 (5) | S6—Zn3—S8 | 117.84 (6) |
S2—Zn1—S3 | 93.03 (5) | S5—Zn3—S8 | 93.23 (5) |
N4—Zn2—N3 | 76.04 (16) | N8—Zn4—N7 | 76.02 (16) |
N4—Zn2—S4 | 84.31 (12) | N8—Zn4—S7 | 83.59 (12) |
N3—Zn2—S4 | 137.85 (12) | N7—Zn4—S7 | 134.94 (12) |
N4—Zn2—S3 | 159.75 (12) | N8—Zn4—S8 | 160.73 (12) |
N3—Zn2—S3 | 83.72 (11) | N7—Zn4—S8 | 84.74 (11) |
S4—Zn2—S3 | 111.68 (5) | S7—Zn4—S8 | 111.50 (5) |
N4—Zn2—S2 | 92.08 (12) | N8—Zn4—S5 | 89.08 (12) |
N3—Zn2—S2 | 103.25 (12) | N7—Zn4—S5 | 103.73 (12) |
S4—Zn2—S2 | 114.53 (6) | S7—Zn4—S5 | 115.80 (5) |
S3—Zn2—S2 | 92.22 (5) | S8—Zn4—S5 | 94.51 (5) |
Zn1—S2—Zn2 | 87.36 (5) | Zn3—S5—Zn4 | 86.33 (5) |
Zn2—S3—Zn1 | 87.31 (5) | Zn4—S8—Zn3 | 85.82 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1B—H1B···S6 | 0.850 (15) | 2.507 (10) | 3.350 (7) | 172 (9) |
C26—H26C···O1Bi | 0.98 | 2.59 | 3.484 (9) | 151 |
C28—H28···O1Bi | 0.95 | 2.56 | 3.444 (9) | 155 |
C28—H28···O1Ai | 0.95 | 2.57 | 3.42 (3) | 149 |
C50—H50···O1Aii | 0.95 | 2.62 | 3.54 (3) | 165 |
C28—H28···S1Ai | 0.95 | 2.99 | 3.740 (18) | 137 |
C8—H8B···S1iii | 0.98 | 2.91 | 3.880 (5) | 170 |
C10—H10C···S1iii | 0.98 | 2.85 | 3.768 (5) | 156 |
C63—H63···S1iii | 0.95 | 2.93 | 3.663 (5) | 135 |
C2—H2···S3iv | 0.95 | 2.93 | 3.742 (6) | 144 |
C42—H42A···S7v | 0.98 | 2.96 | 3.929 (6) | 172 |
C58—H58C···S7vi | 0.98 | 2.83 | 3.787 (5) | 166 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, y, z; (iii) −x+1, −y, −z+1; (iv) −x+2, −y, −z+1; (v) x−1, y, z; (vi) −x+1, −y, −z. |