In the title compound, [Zn(C
16H
16NS
2)
2(C
12H
8N
2)], the Zn
II atom exists within an N
2S
4 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].
Supporting information
CCDC reference: 1550885
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean
(C-C) = 0.006 Å
- R factor = 0.055
- wR factor = 0.181
- Data-to-parameter ratio = 18.9
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT910_ALERT_3_B Missing # of FCF Reflection(s) Below Theta(Min) 12 Note
Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.83 Report
PLAT230_ALERT_2_C Hirshfeld Test Diff for N4 -- C33 .. 5.5 s.u.
PLAT230_ALERT_2_C Hirshfeld Test Diff for C23 -- C24 .. 5.7 s.u.
PLAT241_ALERT_2_C High 'MainMol' Ueq as Compared to Neighbors of C5 Check
PLAT242_ALERT_2_C Low 'MainMol' Ueq as Compared to Neighbors of C11 Check
PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.00614 Ang.
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ...... 4.264 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 24 Report
PLAT973_ALERT_2_C Check Calcd Positive Residual Density on Zn1 1.19 eA-3
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density. 0 Note
Alert level G
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X) Zn1 -- S2 .. 15.6 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X) Zn1 -- S3 .. 8.2 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X) Zn1 -- S4 .. 10.4 s.u.
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 57 Note
0 ALERT level A = Most likely a serious problem - resolve or explain
1 ALERT level B = A potentially serious problem, consider carefully
10 ALERT level C = Check. Ensure it is not caused by an omission or oversight
4 ALERT level G = General information/check it is not something unexpected
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
10 ALERT type 2 Indicator that the structure model may be wrong or deficient
4 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: APEX2 (Bruker, 2004); cell refinement: 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).
Bis[
N-benzyl-
N-(2-phenylethyl)dithiocarbamato-
κ2S,
S'](1,10-phenanthroline
κ2-
N,
N')zinc(II)
top
Crystal data top
[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 |
Data collection top
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 top
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 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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) | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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) | | |
Hydrogen-bond geometry (Å, º) topCg 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. |