metal-organic compounds
Bis[N-benzyl-N-(2-phenylethyl)dithiocarbamato-κ2S,S′](1,10-phenanthroline-κ2N,N′)zinc(II)
aDepartment of Chemistry, Annamalai University, Annamalainagar, Chidambaram 608 002, India, bDepartment of Studies in Physics, University of Mysore, Mysore 570 006, India, and cPG & Research Department of Physics, Government Arts College, Melur 625 106, India
*Correspondence e-mail: rbaskaran54@gmail.com
In the title compound, [Zn(C16H16NS2)2(C12H8N2)], the ZnII atom exists within an N2S4 donor set that defines a distorted octahedral geometry; weak intramolecular C—H⋯S hydrogen bonds are noted. In the crystal, molecules are linked via weak C—H⋯π interactions, forming C(11) chains propagating along [001].
CCDC reference: 1550885
Structure description
Dithiocarbamates are long known to be versatile ligands (Coucouvanis, 1979; Hogarth, 2005) due to their binding capacity to metal atoms, and they can also be used as chemotherapeutics, pesticides and fungicides (Hulanicki, 1967; Ivanov et al., 1999). Dithiocarbamates are the most frequently used bidentate sulfur ligands. In recent years, zinc dithiocarbamates have continued to attract attention on account of their industrial applications (Jones & Jones, 1983). The affinity of zinc towards sulfur-containing ligands leads to many structurally novel complexes (Tiekink, 2003). Metal dithiocarbamate complexes and their nitrogen-donor adducts are useful precursors for the synthesis of metal–sulfide nanoparticles (Srinivasan & Thirumaran, 2012; Yan et al., 1999). In view of the above importance of dithiocarbamate derivatives, we have undertaken the single-crystal X-ray diffraction study of the title compound, and the results are presented herein.
The molecular structure of the title compound is illustrated in Fig. 1. The Zn—S bond lengths are in good agreement with other zinc dithiocarbamate complexes (Kant et al., 2012; Ivanov et al., 2006). The short thiouriede C—N bond lengths indicate that these have significant double-bond character. Similarly, the C—S distances lie between single- and double-bond lengths and prove that these bonds to have partial double-bond character. The zinc metal ion exists within an N2S4 donor set that defines a distorted octahedral geometry. The distortion is due in part to the acute bond angles subtended at zinc by the chelating ligands.
The molecular structure maybe influenced by weak intramolecular C—H⋯S hydrogen bonds (Table 1). In the crystal packing, C—H⋯π interactions link the molecules into C(11) chains propagating along [001]; see Fig. 2 and Table 1. In addition to this, intermolecular π–π interactions are also observed between the centroid of the rings (N4/C33–C36/C44) and (C36–C39/C43–C44) at (−x, −y, 1 − z) with a centroid–centroid distance of 3.766 (2) Å.
Synthesis and crystallization
The title compound was prepared according to the literature procedure (Rani & Thirumaran, 2013). Single crystals were obtained by slow evaporation of dichloromethane and ethyl acetate (2:1) solution of the title compound.
Refinement
Crystal data, data collection and structure . The maximum and minimum residual electron density peaks of 1.11 and 0.39 e Å−3, respectively, are located 0.03 and 0.83 Å from the Zn1 atom.
details are summarized in Table 2Structural data
CCDC reference: 1550885
https://doi.org/10.1107/S2414314617007349/tk4032sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617007349/tk4032Isup2.hkl
Data collection: APEX2 (Bruker, 2004); cell
APEX2/SAINT (Bruker, 2004); data reduction: SAINT/XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).[Zn(C16H16NS2)2(C12H8N2)] | F(000) = 1704 |
Mr = 818.41 | Dx = 1.362 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 16.076 (3) Å | Cell parameters from 12234 reflections |
b = 14.572 (2) Å | θ = 3.3–26.4° |
c = 17.151 (2) Å | µ = 0.86 mm−1 |
β = 96.629 (8)° | T = 298 K |
V = 3990.9 (10) Å3 | Block, brown |
Z = 4 | 0.24 × 0.22 × 0.20 mm |
Bruker Kappa APEXII CCD diffractometer | 6001 reflections with I > 2σ(I) |
Radiation source: Sealed tube | Rint = 0.044 |
ω and φ scan | θmax = 27.5°, θmin = 3.0° |
Absorption correction: multi-scan (SADABS; Bruker, 1999) | h = −20→18 |
Tmin = 0.84, Tmax = 0.85 | k = −18→13 |
18230 measured reflections | l = −12→22 |
9051 independent reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.055 | H-atom parameters constrained |
wR(F2) = 0.181 | w = 1/[σ2(Fo2) + (0.0923P)2 + 1.0518P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
9051 reflections | Δρmax = 1.11 e Å−3 |
478 parameters | Δρmin = −0.39 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
Zn1 | 0.44340 (2) | 0.78266 (2) | 0.11581 (2) | 0.05327 (14) | |
S1 | 0.60074 (5) | 0.76988 (6) | 0.15144 (5) | 0.0606 (2) | |
S2 | 0.47447 (5) | 0.77993 (6) | 0.26228 (5) | 0.0595 (2) | |
S3 | 0.42542 (6) | 0.95155 (6) | 0.09034 (6) | 0.0682 (3) | |
S4 | 0.28729 (6) | 0.81866 (6) | 0.08990 (5) | 0.0601 (2) | |
N1 | 0.63881 (16) | 0.77183 (19) | 0.30803 (16) | 0.0554 (6) | |
N2 | 0.26299 (18) | 0.99571 (19) | 0.05570 (16) | 0.0577 (7) | |
N3 | 0.45893 (16) | 0.7483 (2) | −0.00687 (16) | 0.0556 (6) | |
N4 | 0.41053 (16) | 0.63575 (16) | 0.10380 (14) | 0.0491 (6) | |
C1 | 0.57767 (19) | 0.7727 (2) | 0.2472 (2) | 0.0520 (7) | |
C2 | 0.7285 (2) | 0.7759 (2) | 0.2971 (2) | 0.0591 (8) | |
H2A | 0.7580 | 0.8101 | 0.3403 | 0.071* | |
H2B | 0.7345 | 0.8092 | 0.2491 | 0.071* | |
C3 | 0.76887 (18) | 0.6826 (2) | 0.29289 (19) | 0.0534 (7) | |
C4 | 0.7812 (2) | 0.6460 (3) | 0.2216 (2) | 0.0738 (10) | |
H4 | 0.7627 | 0.6777 | 0.1759 | 0.089* | |
C5 | 0.8207 (3) | 0.5627 (4) | 0.2169 (3) | 0.0990 (15) | |
H5 | 0.8286 | 0.5388 | 0.1680 | 0.119* | |
C6 | 0.8485 (3) | 0.5147 (3) | 0.2834 (3) | 0.0891 (13) | |
H6 | 0.8757 | 0.4587 | 0.2798 | 0.107* | |
C7 | 0.8362 (3) | 0.5492 (3) | 0.3547 (3) | 0.0843 (12) | |
H7 | 0.8542 | 0.5163 | 0.3999 | 0.101* | |
C8 | 0.7970 (2) | 0.6334 (3) | 0.3603 (2) | 0.0717 (10) | |
H8 | 0.7895 | 0.6570 | 0.4094 | 0.086* | |
C9 | 0.6197 (2) | 0.7765 (2) | 0.3904 (2) | 0.0579 (8) | |
H9A | 0.6610 | 0.7417 | 0.4239 | 0.070* | |
H9B | 0.5651 | 0.7498 | 0.3943 | 0.070* | |
C10 | 0.6205 (3) | 0.8758 (3) | 0.4175 (2) | 0.0709 (10) | |
H10A | 0.5821 | 0.9108 | 0.3812 | 0.085* | |
H10B | 0.6762 | 0.9007 | 0.4158 | 0.085* | |
C11 | 0.5962 (2) | 0.8882 (2) | 0.5000 (2) | 0.0620 (8) | |
C12 | 0.6528 (3) | 0.9198 (3) | 0.5598 (2) | 0.0834 (12) | |
H12 | 0.7085 | 0.9280 | 0.5516 | 0.100* | |
C13 | 0.6276 (4) | 0.9396 (4) | 0.6319 (3) | 0.1032 (17) | |
H13 | 0.6661 | 0.9629 | 0.6716 | 0.124* | |
C14 | 0.5475 (5) | 0.9255 (3) | 0.6458 (3) | 0.1020 (17) | |
H14 | 0.5310 | 0.9391 | 0.6947 | 0.122* | |
C15 | 0.4910 (4) | 0.8914 (4) | 0.5876 (4) | 0.1061 (17) | |
H15 | 0.4361 | 0.8805 | 0.5972 | 0.127* | |
C16 | 0.5147 (3) | 0.8730 (3) | 0.5151 (3) | 0.0905 (13) | |
H16 | 0.4756 | 0.8502 | 0.4757 | 0.109* | |
C17 | 0.3196 (2) | 0.9295 (2) | 0.07673 (19) | 0.0549 (7) | |
C18 | 0.1722 (2) | 0.9789 (3) | 0.0535 (2) | 0.0612 (8) | |
H18A | 0.1588 | 0.9197 | 0.0294 | 0.073* | |
H18B | 0.1419 | 1.0255 | 0.0213 | 0.073* | |
C19 | 0.1441 (2) | 0.9805 (3) | 0.1350 (2) | 0.0713 (10) | |
H19A | 0.1762 | 0.9356 | 0.1676 | 0.086* | |
H19B | 0.1561 | 1.0405 | 0.1581 | 0.086* | |
C20 | 0.0524 (2) | 0.9604 (3) | 0.13529 (19) | 0.0609 (8) | |
C21 | 0.0215 (3) | 0.8714 (3) | 0.1240 (2) | 0.0761 (11) | |
H21 | 0.0574 | 0.8239 | 0.1140 | 0.091* | |
C22 | −0.0627 (3) | 0.8534 (4) | 0.1278 (3) | 0.0906 (14) | |
H22 | −0.0831 | 0.7941 | 0.1193 | 0.109* | |
C23 | −0.1160 (3) | 0.9227 (5) | 0.1439 (2) | 0.0968 (16) | |
H23 | −0.1720 | 0.9100 | 0.1480 | 0.116* | |
C24 | −0.0866 (3) | 1.0097 (4) | 0.1540 (2) | 0.0877 (14) | |
H24 | −0.1229 | 1.0568 | 0.1640 | 0.105* | |
C25 | −0.0040 (2) | 1.0288 (3) | 0.1495 (2) | 0.0709 (10) | |
H25 | 0.0147 | 1.0889 | 0.1561 | 0.085* | |
C26 | 0.2877 (2) | 1.0887 (2) | 0.0327 (2) | 0.0646 (9) | |
H26A | 0.2597 | 1.1024 | −0.0191 | 0.078* | |
H26B | 0.3476 | 1.0893 | 0.0295 | 0.078* | |
C27 | 0.2670 (2) | 1.1634 (2) | 0.0890 (2) | 0.0592 (8) | |
C28 | 0.2173 (2) | 1.2358 (3) | 0.0622 (3) | 0.0720 (10) | |
H28 | 0.1962 | 1.2395 | 0.0094 | 0.086* | |
C29 | 0.1986 (3) | 1.3047 (3) | 0.1149 (3) | 0.0844 (12) | |
H29 | 0.1658 | 1.3546 | 0.0968 | 0.101* | |
C30 | 0.2283 (3) | 1.2984 (3) | 0.1924 (3) | 0.0787 (11) | |
H30 | 0.2147 | 1.3434 | 0.2273 | 0.094* | |
C31 | 0.2776 (3) | 1.2270 (3) | 0.2188 (3) | 0.0806 (12) | |
H31 | 0.2984 | 1.2237 | 0.2716 | 0.097* | |
C32 | 0.2970 (3) | 1.1591 (3) | 0.1679 (2) | 0.0747 (10) | |
H32 | 0.3305 | 1.1101 | 0.1867 | 0.090* | |
C33 | 0.3880 (2) | 0.5807 (2) | 0.1593 (2) | 0.0621 (8) | |
H33 | 0.3874 | 0.6039 | 0.2098 | 0.075* | |
C34 | 0.3651 (2) | 0.4894 (3) | 0.1449 (3) | 0.0725 (10) | |
H34 | 0.3509 | 0.4524 | 0.1855 | 0.087* | |
C35 | 0.3637 (2) | 0.4550 (3) | 0.0712 (3) | 0.0726 (10) | |
H35 | 0.3477 | 0.3944 | 0.0611 | 0.087* | |
C36 | 0.3863 (2) | 0.5104 (2) | 0.0104 (2) | 0.0625 (9) | |
C37 | 0.3880 (2) | 0.4803 (3) | −0.0691 (3) | 0.0794 (12) | |
H37 | 0.3716 | 0.4207 | −0.0830 | 0.095* | |
C38 | 0.4129 (3) | 0.5371 (3) | −0.1234 (3) | 0.0816 (12) | |
H38 | 0.4130 | 0.5157 | −0.1745 | 0.098* | |
C39 | 0.4390 (2) | 0.6287 (3) | −0.1058 (2) | 0.0690 (10) | |
C40 | 0.4692 (3) | 0.6887 (4) | −0.1596 (2) | 0.0883 (14) | |
H40 | 0.4731 | 0.6696 | −0.2107 | 0.106* | |
C41 | 0.4930 (3) | 0.7753 (4) | −0.1366 (3) | 0.0898 (15) | |
H41 | 0.5135 | 0.8155 | −0.1720 | 0.108* | |
C42 | 0.4863 (2) | 0.8031 (3) | −0.0601 (2) | 0.0728 (10) | |
H42 | 0.5016 | 0.8628 | −0.0456 | 0.087* | |
C43 | 0.43604 (18) | 0.6620 (2) | −0.02923 (18) | 0.0525 (7) | |
C44 | 0.40974 (17) | 0.6017 (2) | 0.02984 (18) | 0.0486 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.0580 (2) | 0.0468 (2) | 0.0536 (2) | −0.00002 (15) | 0.00018 (17) | −0.00421 (16) |
S1 | 0.0571 (5) | 0.0653 (5) | 0.0581 (5) | 0.0045 (4) | 0.0014 (4) | −0.0148 (4) |
S2 | 0.0494 (4) | 0.0664 (5) | 0.0614 (5) | 0.0048 (4) | 0.0010 (4) | −0.0096 (4) |
S3 | 0.0610 (5) | 0.0534 (5) | 0.0898 (7) | −0.0001 (4) | 0.0067 (5) | 0.0041 (5) |
S4 | 0.0629 (5) | 0.0519 (5) | 0.0657 (5) | 0.0007 (4) | 0.0082 (4) | 0.0078 (4) |
N1 | 0.0489 (14) | 0.0607 (17) | 0.0551 (15) | 0.0023 (12) | −0.0001 (12) | −0.0111 (12) |
N2 | 0.0642 (16) | 0.0549 (15) | 0.0533 (15) | 0.0067 (13) | 0.0033 (12) | 0.0009 (12) |
N3 | 0.0543 (14) | 0.0599 (16) | 0.0518 (15) | −0.0003 (13) | 0.0029 (12) | 0.0055 (13) |
N4 | 0.0557 (14) | 0.0428 (13) | 0.0490 (14) | −0.0008 (11) | 0.0073 (11) | −0.0019 (11) |
C1 | 0.0513 (16) | 0.0419 (16) | 0.0604 (19) | −0.0001 (12) | −0.0037 (14) | −0.0103 (13) |
C2 | 0.0492 (16) | 0.059 (2) | 0.066 (2) | −0.0035 (14) | −0.0030 (15) | −0.0088 (16) |
C3 | 0.0407 (14) | 0.0590 (19) | 0.0592 (18) | −0.0035 (13) | 0.0008 (13) | −0.0049 (15) |
C4 | 0.080 (2) | 0.079 (3) | 0.062 (2) | 0.018 (2) | 0.0058 (18) | −0.0100 (19) |
C5 | 0.107 (3) | 0.093 (3) | 0.097 (3) | 0.033 (3) | 0.011 (3) | −0.028 (3) |
C6 | 0.078 (3) | 0.058 (2) | 0.131 (4) | 0.011 (2) | 0.008 (3) | 0.004 (3) |
C7 | 0.070 (2) | 0.086 (3) | 0.097 (3) | 0.010 (2) | 0.011 (2) | 0.034 (3) |
C8 | 0.060 (2) | 0.089 (3) | 0.065 (2) | 0.0057 (19) | 0.0032 (17) | 0.003 (2) |
C9 | 0.0608 (18) | 0.0516 (18) | 0.0596 (19) | 0.0034 (14) | −0.0007 (15) | −0.0028 (15) |
C10 | 0.089 (3) | 0.059 (2) | 0.064 (2) | −0.0055 (19) | 0.0059 (19) | −0.0022 (17) |
C11 | 0.074 (2) | 0.0536 (18) | 0.0574 (19) | −0.0016 (16) | 0.0024 (16) | −0.0027 (15) |
C12 | 0.086 (3) | 0.099 (3) | 0.062 (2) | −0.015 (2) | −0.005 (2) | −0.008 (2) |
C13 | 0.153 (5) | 0.100 (4) | 0.053 (2) | −0.022 (3) | −0.003 (3) | −0.005 (2) |
C14 | 0.165 (5) | 0.077 (3) | 0.072 (3) | 0.016 (3) | 0.050 (3) | 0.000 (2) |
C15 | 0.103 (4) | 0.104 (4) | 0.120 (4) | 0.006 (3) | 0.051 (4) | 0.001 (3) |
C16 | 0.078 (3) | 0.098 (3) | 0.096 (3) | −0.004 (2) | 0.011 (2) | −0.016 (3) |
C17 | 0.0644 (18) | 0.0510 (17) | 0.0501 (17) | 0.0059 (15) | 0.0098 (14) | 0.0010 (14) |
C18 | 0.0623 (19) | 0.065 (2) | 0.0545 (19) | 0.0067 (16) | −0.0006 (15) | 0.0010 (16) |
C19 | 0.074 (2) | 0.085 (3) | 0.054 (2) | 0.005 (2) | 0.0047 (17) | −0.0108 (18) |
C20 | 0.0639 (19) | 0.068 (2) | 0.0490 (17) | 0.0059 (17) | 0.0014 (14) | −0.0074 (16) |
C21 | 0.083 (3) | 0.073 (3) | 0.071 (2) | 0.005 (2) | 0.002 (2) | −0.003 (2) |
C22 | 0.091 (3) | 0.101 (3) | 0.075 (3) | −0.026 (3) | −0.009 (2) | 0.010 (2) |
C23 | 0.066 (2) | 0.167 (6) | 0.055 (2) | 0.001 (3) | −0.0039 (19) | 0.016 (3) |
C24 | 0.074 (3) | 0.123 (4) | 0.063 (2) | 0.030 (3) | −0.004 (2) | −0.005 (3) |
C25 | 0.073 (2) | 0.074 (2) | 0.064 (2) | 0.0131 (19) | −0.0002 (18) | −0.0025 (19) |
C26 | 0.081 (2) | 0.0561 (19) | 0.0562 (19) | 0.0052 (17) | 0.0066 (17) | 0.0082 (16) |
C27 | 0.0578 (18) | 0.0548 (19) | 0.064 (2) | −0.0002 (15) | 0.0053 (15) | −0.0006 (16) |
C28 | 0.073 (2) | 0.060 (2) | 0.080 (3) | 0.0028 (18) | −0.0090 (19) | −0.0021 (19) |
C29 | 0.074 (2) | 0.057 (2) | 0.121 (4) | 0.0095 (19) | 0.008 (3) | −0.010 (2) |
C30 | 0.075 (2) | 0.070 (3) | 0.092 (3) | −0.012 (2) | 0.018 (2) | −0.023 (2) |
C31 | 0.088 (3) | 0.082 (3) | 0.073 (3) | −0.010 (2) | 0.012 (2) | −0.020 (2) |
C32 | 0.086 (3) | 0.072 (2) | 0.064 (2) | 0.010 (2) | 0.0000 (19) | −0.0037 (19) |
C33 | 0.071 (2) | 0.0561 (19) | 0.0590 (19) | 0.0010 (16) | 0.0060 (16) | 0.0014 (16) |
C34 | 0.072 (2) | 0.055 (2) | 0.091 (3) | −0.0109 (17) | 0.010 (2) | 0.010 (2) |
C35 | 0.062 (2) | 0.0501 (19) | 0.104 (3) | −0.0102 (16) | 0.000 (2) | −0.010 (2) |
C36 | 0.0527 (17) | 0.0552 (19) | 0.077 (2) | 0.0012 (15) | −0.0032 (16) | −0.0199 (18) |
C37 | 0.068 (2) | 0.077 (3) | 0.089 (3) | 0.006 (2) | −0.008 (2) | −0.044 (2) |
C38 | 0.079 (3) | 0.100 (3) | 0.063 (2) | 0.015 (2) | −0.004 (2) | −0.037 (2) |
C39 | 0.0568 (19) | 0.098 (3) | 0.0502 (19) | 0.0176 (19) | −0.0021 (15) | −0.0117 (19) |
C40 | 0.077 (3) | 0.139 (4) | 0.049 (2) | 0.025 (3) | 0.0095 (19) | −0.001 (3) |
C41 | 0.078 (3) | 0.129 (5) | 0.065 (3) | 0.008 (3) | 0.019 (2) | 0.029 (3) |
C42 | 0.065 (2) | 0.082 (3) | 0.072 (2) | −0.0064 (19) | 0.0103 (18) | 0.020 (2) |
C43 | 0.0453 (15) | 0.0644 (19) | 0.0468 (16) | 0.0036 (14) | 0.0005 (12) | −0.0076 (15) |
C44 | 0.0427 (14) | 0.0475 (16) | 0.0536 (17) | 0.0002 (12) | −0.0029 (12) | −0.0077 (13) |
Zn1—N3 | 2.205 (3) | C18—C19 | 1.519 (5) |
Zn1—N4 | 2.209 (2) | C18—H18A | 0.9700 |
Zn1—S2 | 2.5043 (10) | C18—H18B | 0.9700 |
Zn1—S3 | 2.5103 (11) | C19—C20 | 1.504 (5) |
Zn1—S1 | 2.5394 (10) | C19—H19A | 0.9700 |
Zn1—S4 | 2.5522 (10) | C19—H19B | 0.9700 |
S1—C1 | 1.725 (3) | C20—C25 | 1.387 (5) |
S2—C1 | 1.712 (3) | C20—C21 | 1.395 (6) |
S3—C17 | 1.721 (4) | C21—C22 | 1.386 (6) |
S4—C17 | 1.719 (3) | C21—H21 | 0.9300 |
N1—C1 | 1.349 (4) | C22—C23 | 1.373 (7) |
N1—C2 | 1.476 (4) | C22—H22 | 0.9300 |
N1—C9 | 1.482 (4) | C23—C24 | 1.358 (7) |
N2—C17 | 1.347 (4) | C23—H23 | 0.9300 |
N2—C18 | 1.475 (4) | C24—C25 | 1.366 (6) |
N2—C26 | 1.478 (4) | C24—H24 | 0.9300 |
N3—C42 | 1.326 (4) | C25—H25 | 0.9300 |
N3—C43 | 1.353 (4) | C26—C27 | 1.518 (5) |
N4—C33 | 1.327 (4) | C26—H26A | 0.9700 |
N4—C44 | 1.361 (4) | C26—H26B | 0.9700 |
C2—C3 | 1.512 (5) | C27—C28 | 1.371 (5) |
C2—H2A | 0.9700 | C27—C32 | 1.383 (5) |
C2—H2B | 0.9700 | C28—C29 | 1.407 (6) |
C3—C4 | 1.369 (5) | C28—H28 | 0.9300 |
C3—C8 | 1.391 (5) | C29—C30 | 1.363 (6) |
C4—C5 | 1.377 (6) | C29—H29 | 0.9300 |
C4—H4 | 0.9300 | C30—C31 | 1.354 (6) |
C5—C6 | 1.369 (7) | C30—H30 | 0.9300 |
C5—H5 | 0.9300 | C31—C32 | 1.380 (5) |
C6—C7 | 1.357 (6) | C31—H31 | 0.9300 |
C6—H6 | 0.9300 | C32—H32 | 0.9300 |
C7—C8 | 1.387 (6) | C33—C34 | 1.394 (5) |
C7—H7 | 0.9300 | C33—H33 | 0.9300 |
C8—H8 | 0.9300 | C34—C35 | 1.359 (6) |
C9—C10 | 1.519 (5) | C34—H34 | 0.9300 |
C9—H9A | 0.9700 | C35—C36 | 1.399 (5) |
C9—H9B | 0.9700 | C35—H35 | 0.9300 |
C10—C11 | 1.520 (5) | C36—C44 | 1.413 (4) |
C10—H10A | 0.9700 | C36—C37 | 1.435 (5) |
C10—H10B | 0.9700 | C37—C38 | 1.342 (6) |
C11—C12 | 1.371 (5) | C37—H37 | 0.9300 |
C11—C16 | 1.382 (6) | C38—C39 | 1.421 (6) |
C12—C13 | 1.375 (6) | C38—H38 | 0.9300 |
C12—H12 | 0.9300 | C39—C40 | 1.398 (6) |
C13—C14 | 1.352 (8) | C39—C43 | 1.407 (4) |
C13—H13 | 0.9300 | C40—C41 | 1.363 (7) |
C14—C15 | 1.364 (8) | C40—H40 | 0.9300 |
C14—H14 | 0.9300 | C41—C42 | 1.389 (6) |
C15—C16 | 1.368 (7) | C41—H41 | 0.9300 |
C15—H15 | 0.9300 | C42—H42 | 0.9300 |
C16—H16 | 0.9300 | C43—C44 | 1.441 (5) |
N3—Zn1—N4 | 75.10 (10) | N2—C18—C19 | 111.9 (3) |
N3—Zn1—S2 | 157.24 (8) | N2—C18—H18A | 109.2 |
N4—Zn1—S2 | 95.51 (7) | C19—C18—H18A | 109.2 |
N3—Zn1—S3 | 94.60 (8) | N2—C18—H18B | 109.2 |
N4—Zn1—S3 | 155.83 (7) | C19—C18—H18B | 109.2 |
S2—Zn1—S3 | 101.29 (3) | H18A—C18—H18B | 107.9 |
N3—Zn1—S1 | 89.63 (7) | C20—C19—C18 | 113.4 (3) |
N4—Zn1—S1 | 99.92 (7) | C20—C19—H19A | 108.9 |
S2—Zn1—S1 | 71.32 (3) | C18—C19—H19A | 108.9 |
S3—Zn1—S1 | 101.84 (3) | C20—C19—H19B | 108.9 |
N3—Zn1—S4 | 95.62 (7) | C18—C19—H19B | 108.9 |
N4—Zn1—S4 | 87.89 (7) | H19A—C19—H19B | 107.7 |
S2—Zn1—S4 | 104.85 (3) | C25—C20—C21 | 117.5 (4) |
S3—Zn1—S4 | 71.16 (3) | C25—C20—C19 | 121.5 (4) |
S1—Zn1—S4 | 171.52 (3) | C21—C20—C19 | 121.0 (3) |
C1—S1—Zn1 | 84.82 (11) | C22—C21—C20 | 120.2 (4) |
C1—S2—Zn1 | 86.19 (12) | C22—C21—H21 | 119.9 |
C17—S3—Zn1 | 86.12 (11) | C20—C21—H21 | 119.9 |
C17—S4—Zn1 | 84.84 (12) | C23—C22—C21 | 120.4 (5) |
C1—N1—C2 | 122.4 (3) | C23—C22—H22 | 119.8 |
C1—N1—C9 | 121.7 (3) | C21—C22—H22 | 119.8 |
C2—N1—C9 | 115.6 (3) | C24—C23—C22 | 119.7 (4) |
C17—N2—C18 | 121.6 (3) | C24—C23—H23 | 120.1 |
C17—N2—C26 | 122.3 (3) | C22—C23—H23 | 120.1 |
C18—N2—C26 | 116.2 (3) | C23—C24—C25 | 120.6 (4) |
C42—N3—C43 | 117.7 (3) | C23—C24—H24 | 119.7 |
C42—N3—Zn1 | 127.1 (3) | C25—C24—H24 | 119.7 |
C43—N3—Zn1 | 115.1 (2) | C24—C25—C20 | 121.5 (4) |
C33—N4—C44 | 118.3 (3) | C24—C25—H25 | 119.2 |
C33—N4—Zn1 | 126.9 (2) | C20—C25—H25 | 119.2 |
C44—N4—Zn1 | 114.61 (19) | N2—C26—C27 | 113.7 (3) |
N1—C1—S2 | 121.0 (3) | N2—C26—H26A | 108.8 |
N1—C1—S1 | 121.3 (2) | C27—C26—H26A | 108.8 |
S2—C1—S1 | 117.67 (19) | N2—C26—H26B | 108.8 |
N1—C2—C3 | 113.6 (3) | C27—C26—H26B | 108.8 |
N1—C2—H2A | 108.8 | H26A—C26—H26B | 107.7 |
C3—C2—H2A | 108.8 | C28—C27—C32 | 119.1 (4) |
N1—C2—H2B | 108.8 | C28—C27—C26 | 120.0 (3) |
C3—C2—H2B | 108.8 | C32—C27—C26 | 120.8 (3) |
H2A—C2—H2B | 107.7 | C27—C28—C29 | 119.5 (4) |
C4—C3—C8 | 118.3 (3) | C27—C28—H28 | 120.2 |
C4—C3—C2 | 120.1 (3) | C29—C28—H28 | 120.2 |
C8—C3—C2 | 121.6 (3) | C30—C29—C28 | 120.2 (4) |
C3—C4—C5 | 120.8 (4) | C30—C29—H29 | 119.9 |
C3—C4—H4 | 119.6 | C28—C29—H29 | 119.9 |
C5—C4—H4 | 119.6 | C31—C30—C29 | 120.2 (4) |
C6—C5—C4 | 120.6 (4) | C31—C30—H30 | 119.9 |
C6—C5—H5 | 119.7 | C29—C30—H30 | 119.9 |
C4—C5—H5 | 119.7 | C30—C31—C32 | 120.4 (4) |
C7—C6—C5 | 119.6 (4) | C30—C31—H31 | 119.8 |
C7—C6—H6 | 120.2 | C32—C31—H31 | 119.8 |
C5—C6—H6 | 120.2 | C31—C32—C27 | 120.5 (4) |
C6—C7—C8 | 120.4 (4) | C31—C32—H32 | 119.7 |
C6—C7—H7 | 119.8 | C27—C32—H32 | 119.7 |
C8—C7—H7 | 119.8 | N4—C33—C34 | 122.5 (3) |
C7—C8—C3 | 120.3 (4) | N4—C33—H33 | 118.7 |
C7—C8—H8 | 119.8 | C34—C33—H33 | 118.7 |
C3—C8—H8 | 119.8 | C35—C34—C33 | 119.5 (4) |
N1—C9—C10 | 109.9 (3) | C35—C34—H34 | 120.2 |
N1—C9—H9A | 109.7 | C33—C34—H34 | 120.2 |
C10—C9—H9A | 109.7 | C34—C35—C36 | 120.2 (3) |
N1—C9—H9B | 109.7 | C34—C35—H35 | 119.9 |
C10—C9—H9B | 109.7 | C36—C35—H35 | 119.9 |
H9A—C9—H9B | 108.2 | C35—C36—C44 | 116.9 (3) |
C9—C10—C11 | 113.8 (3) | C35—C36—C37 | 124.5 (4) |
C9—C10—H10A | 108.8 | C44—C36—C37 | 118.6 (4) |
C11—C10—H10A | 108.8 | C38—C37—C36 | 120.7 (4) |
C9—C10—H10B | 108.8 | C38—C37—H37 | 119.6 |
C11—C10—H10B | 108.8 | C36—C37—H37 | 119.6 |
H10A—C10—H10B | 107.7 | C37—C38—C39 | 122.4 (4) |
C12—C11—C16 | 118.3 (4) | C37—C38—H38 | 118.8 |
C12—C11—C10 | 121.1 (4) | C39—C38—H38 | 118.8 |
C16—C11—C10 | 120.5 (4) | C40—C39—C43 | 116.8 (4) |
C11—C12—C13 | 120.3 (5) | C40—C39—C38 | 124.4 (4) |
C11—C12—H12 | 119.8 | C43—C39—C38 | 118.8 (4) |
C13—C12—H12 | 119.8 | C41—C40—C39 | 119.8 (4) |
C14—C13—C12 | 120.8 (5) | C41—C40—H40 | 120.1 |
C14—C13—H13 | 119.6 | C39—C40—H40 | 120.1 |
C12—C13—H13 | 119.6 | C40—C41—C42 | 119.5 (4) |
C13—C14—C15 | 119.6 (4) | C40—C41—H41 | 120.2 |
C13—C14—H14 | 120.2 | C42—C41—H41 | 120.2 |
C15—C14—H14 | 120.2 | N3—C42—C41 | 122.9 (4) |
C14—C15—C16 | 120.3 (5) | N3—C42—H42 | 118.6 |
C14—C15—H15 | 119.8 | C41—C42—H42 | 118.6 |
C16—C15—H15 | 119.8 | N3—C43—C39 | 123.2 (3) |
C15—C16—C11 | 120.6 (5) | N3—C43—C44 | 117.4 (3) |
C15—C16—H16 | 119.7 | C39—C43—C44 | 119.4 (3) |
C11—C16—H16 | 119.7 | N4—C44—C36 | 122.5 (3) |
N2—C17—S4 | 120.2 (3) | N4—C44—C43 | 117.5 (3) |
N2—C17—S3 | 121.9 (3) | C36—C44—C43 | 120.0 (3) |
S4—C17—S3 | 117.83 (19) | ||
C2—N1—C1—S2 | −173.1 (2) | C21—C20—C25—C24 | 1.4 (5) |
C9—N1—C1—S2 | 0.4 (4) | C19—C20—C25—C24 | −176.4 (4) |
C2—N1—C1—S1 | 5.0 (4) | C17—N2—C26—C27 | −114.4 (4) |
C9—N1—C1—S1 | 178.5 (2) | C18—N2—C26—C27 | 66.2 (4) |
Zn1—S2—C1—N1 | 177.3 (3) | N2—C26—C27—C28 | −122.9 (4) |
Zn1—S2—C1—S1 | −0.82 (16) | N2—C26—C27—C32 | 56.6 (5) |
Zn1—S1—C1—N1 | −177.3 (3) | C32—C27—C28—C29 | 0.6 (6) |
Zn1—S1—C1—S2 | 0.81 (16) | C26—C27—C28—C29 | −180.0 (4) |
C1—N1—C2—C3 | −92.6 (4) | C27—C28—C29—C30 | −1.2 (6) |
C9—N1—C2—C3 | 93.6 (3) | C28—C29—C30—C31 | 1.5 (7) |
N1—C2—C3—C4 | 100.2 (4) | C29—C30—C31—C32 | −1.1 (7) |
N1—C2—C3—C8 | −82.0 (4) | C30—C31—C32—C27 | 0.5 (6) |
C8—C3—C4—C5 | −0.2 (6) | C28—C27—C32—C31 | −0.2 (6) |
C2—C3—C4—C5 | 177.6 (4) | C26—C27—C32—C31 | −179.7 (4) |
C3—C4—C5—C6 | 0.0 (7) | C44—N4—C33—C34 | 1.1 (5) |
C4—C5—C6—C7 | 0.7 (8) | Zn1—N4—C33—C34 | 177.3 (3) |
C5—C6—C7—C8 | −1.1 (7) | N4—C33—C34—C35 | −1.5 (6) |
C6—C7—C8—C3 | 0.9 (6) | C33—C34—C35—C36 | 0.9 (6) |
C4—C3—C8—C7 | −0.2 (5) | C34—C35—C36—C44 | −0.1 (5) |
C2—C3—C8—C7 | −178.0 (3) | C34—C35—C36—C37 | 179.1 (4) |
C1—N1—C9—C10 | −92.1 (4) | C35—C36—C37—C38 | −177.9 (4) |
C2—N1—C9—C10 | 81.8 (4) | C44—C36—C37—C38 | 1.3 (5) |
N1—C9—C10—C11 | 176.4 (3) | C36—C37—C38—C39 | 0.3 (6) |
C9—C10—C11—C12 | 114.3 (4) | C37—C38—C39—C40 | 176.8 (4) |
C9—C10—C11—C16 | −69.7 (5) | C37—C38—C39—C43 | −2.2 (6) |
C16—C11—C12—C13 | −2.8 (7) | C43—C39—C40—C41 | −0.9 (6) |
C10—C11—C12—C13 | 173.3 (4) | C38—C39—C40—C41 | −179.8 (4) |
C11—C12—C13—C14 | 2.0 (8) | C39—C40—C41—C42 | −0.4 (7) |
C12—C13—C14—C15 | 0.0 (8) | C43—N3—C42—C41 | −0.7 (5) |
C13—C14—C15—C16 | −1.3 (9) | Zn1—N3—C42—C41 | −179.2 (3) |
C14—C15—C16—C11 | 0.5 (8) | C40—C41—C42—N3 | 1.3 (7) |
C12—C11—C16—C15 | 1.5 (7) | C42—N3—C43—C39 | −0.8 (5) |
C10—C11—C16—C15 | −174.6 (4) | Zn1—N3—C43—C39 | 177.9 (2) |
C18—N2—C17—S4 | 8.2 (4) | C42—N3—C43—C44 | 177.5 (3) |
C26—N2—C17—S4 | −171.1 (2) | Zn1—N3—C43—C44 | −3.8 (3) |
C18—N2—C17—S3 | −172.5 (2) | C40—C39—C43—N3 | 1.5 (5) |
C26—N2—C17—S3 | 8.3 (4) | C38—C39—C43—N3 | −179.5 (3) |
Zn1—S4—C17—N2 | 177.3 (3) | C40—C39—C43—C44 | −176.7 (3) |
Zn1—S4—C17—S3 | −2.12 (17) | C38—C39—C43—C44 | 2.3 (5) |
Zn1—S3—C17—N2 | −177.2 (3) | C33—N4—C44—C36 | −0.3 (4) |
Zn1—S3—C17—S4 | 2.15 (17) | Zn1—N4—C44—C36 | −176.9 (2) |
C17—N2—C18—C19 | 77.9 (4) | C33—N4—C44—C43 | −178.8 (3) |
C26—N2—C18—C19 | −102.8 (4) | Zn1—N4—C44—C43 | 4.6 (3) |
N2—C18—C19—C20 | −178.0 (3) | C35—C36—C44—N4 | −0.2 (5) |
C18—C19—C20—C25 | −107.5 (4) | C37—C36—C44—N4 | −179.5 (3) |
C18—C19—C20—C21 | 74.8 (5) | C35—C36—C44—C43 | 178.2 (3) |
C25—C20—C21—C22 | −0.5 (6) | C37—C36—C44—C43 | −1.1 (5) |
C19—C20—C21—C22 | 177.3 (4) | N3—C43—C44—N4 | −0.5 (4) |
C20—C21—C22—C23 | −1.2 (6) | C39—C43—C44—N4 | 177.8 (3) |
C21—C22—C23—C24 | 2.0 (7) | N3—C43—C44—C36 | −179.1 (3) |
C22—C23—C24—C25 | −1.1 (7) | C39—C43—C44—C36 | −0.8 (4) |
C23—C24—C25—C20 | −0.6 (6) |
Cg is the centroid of the N1/C33–C36/C44 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2B···S1 | 0.97 | 2.63 | 3.046 (4) | 106 |
C9—H9B···S2 | 0.97 | 2.59 | 3.016 (4) | 107 |
C18—H18A···S4 | 0.97 | 2.65 | 3.000 (4) | 102 |
C26—H26B···S3 | 0.97 | 2.53 | 3.060 (4) | 115 |
C12—H12···Cgi | 0.93 | 2.89 | 3.777 (5) | 160 |
Symmetry code: (i) x−3/2, −y−1/2, z−3/2. |
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