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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].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314617007349/tk4032sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2414314617007349/tk4032Isup2.hkl
Contains datablock I

CCDC reference: 1550885

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.055
  • wR factor = 0.181
  • Data-to-parameter ratio = 18.9

checkCIF/PLATON results

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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

Computing details top

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-phenanthrolineκ2-N,N')zinc(II) top
Crystal data top
[Zn(C16H16NS2)2(C12H8N2)]F(000) = 1704
Mr = 818.41Dx = 1.362 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 16.076 (3) ÅCell parameters from 12234 reflections
b = 14.572 (2) Åθ = 3.3–26.4°
c = 17.151 (2) ŵ = 0.86 mm1
β = 96.629 (8)°T = 298 K
V = 3990.9 (10) Å3Block, brown
Z = 40.24 × 0.22 × 0.20 mm
Data collection top
Bruker Kappa APEXII CCD
diffractometer
6001 reflections with I > 2σ(I)
Radiation source: Sealed tubeRint = 0.044
ω and φ scanθmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan
(SADABS; Bruker, 1999)
h = 2018
Tmin = 0.84, Tmax = 0.85k = 1813
18230 measured reflectionsl = 1222
9051 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.055H-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 reflectionsΔρmax = 1.11 e Å3
478 parametersΔρmin = 0.39 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Zn10.44340 (2)0.78266 (2)0.11581 (2)0.05327 (14)
S10.60074 (5)0.76988 (6)0.15144 (5)0.0606 (2)
S20.47447 (5)0.77993 (6)0.26228 (5)0.0595 (2)
S30.42542 (6)0.95155 (6)0.09034 (6)0.0682 (3)
S40.28729 (6)0.81866 (6)0.08990 (5)0.0601 (2)
N10.63881 (16)0.77183 (19)0.30803 (16)0.0554 (6)
N20.26299 (18)0.99571 (19)0.05570 (16)0.0577 (7)
N30.45893 (16)0.7483 (2)0.00687 (16)0.0556 (6)
N40.41053 (16)0.63575 (16)0.10380 (14)0.0491 (6)
C10.57767 (19)0.7727 (2)0.2472 (2)0.0520 (7)
C20.7285 (2)0.7759 (2)0.2971 (2)0.0591 (8)
H2A0.75800.81010.34030.071*
H2B0.73450.80920.24910.071*
C30.76887 (18)0.6826 (2)0.29289 (19)0.0534 (7)
C40.7812 (2)0.6460 (3)0.2216 (2)0.0738 (10)
H40.76270.67770.17590.089*
C50.8207 (3)0.5627 (4)0.2169 (3)0.0990 (15)
H50.82860.53880.16800.119*
C60.8485 (3)0.5147 (3)0.2834 (3)0.0891 (13)
H60.87570.45870.27980.107*
C70.8362 (3)0.5492 (3)0.3547 (3)0.0843 (12)
H70.85420.51630.39990.101*
C80.7970 (2)0.6334 (3)0.3603 (2)0.0717 (10)
H80.78950.65700.40940.086*
C90.6197 (2)0.7765 (2)0.3904 (2)0.0579 (8)
H9A0.66100.74170.42390.070*
H9B0.56510.74980.39430.070*
C100.6205 (3)0.8758 (3)0.4175 (2)0.0709 (10)
H10A0.58210.91080.38120.085*
H10B0.67620.90070.41580.085*
C110.5962 (2)0.8882 (2)0.5000 (2)0.0620 (8)
C120.6528 (3)0.9198 (3)0.5598 (2)0.0834 (12)
H120.70850.92800.55160.100*
C130.6276 (4)0.9396 (4)0.6319 (3)0.1032 (17)
H130.66610.96290.67160.124*
C140.5475 (5)0.9255 (3)0.6458 (3)0.1020 (17)
H140.53100.93910.69470.122*
C150.4910 (4)0.8914 (4)0.5876 (4)0.1061 (17)
H150.43610.88050.59720.127*
C160.5147 (3)0.8730 (3)0.5151 (3)0.0905 (13)
H160.47560.85020.47570.109*
C170.3196 (2)0.9295 (2)0.07673 (19)0.0549 (7)
C180.1722 (2)0.9789 (3)0.0535 (2)0.0612 (8)
H18A0.15880.91970.02940.073*
H18B0.14191.02550.02130.073*
C190.1441 (2)0.9805 (3)0.1350 (2)0.0713 (10)
H19A0.17620.93560.16760.086*
H19B0.15611.04050.15810.086*
C200.0524 (2)0.9604 (3)0.13529 (19)0.0609 (8)
C210.0215 (3)0.8714 (3)0.1240 (2)0.0761 (11)
H210.05740.82390.11400.091*
C220.0627 (3)0.8534 (4)0.1278 (3)0.0906 (14)
H220.08310.79410.11930.109*
C230.1160 (3)0.9227 (5)0.1439 (2)0.0968 (16)
H230.17200.91000.14800.116*
C240.0866 (3)1.0097 (4)0.1540 (2)0.0877 (14)
H240.12291.05680.16400.105*
C250.0040 (2)1.0288 (3)0.1495 (2)0.0709 (10)
H250.01471.08890.15610.085*
C260.2877 (2)1.0887 (2)0.0327 (2)0.0646 (9)
H26A0.25971.10240.01910.078*
H26B0.34761.08930.02950.078*
C270.2670 (2)1.1634 (2)0.0890 (2)0.0592 (8)
C280.2173 (2)1.2358 (3)0.0622 (3)0.0720 (10)
H280.19621.23950.00940.086*
C290.1986 (3)1.3047 (3)0.1149 (3)0.0844 (12)
H290.16581.35460.09680.101*
C300.2283 (3)1.2984 (3)0.1924 (3)0.0787 (11)
H300.21471.34340.22730.094*
C310.2776 (3)1.2270 (3)0.2188 (3)0.0806 (12)
H310.29841.22370.27160.097*
C320.2970 (3)1.1591 (3)0.1679 (2)0.0747 (10)
H320.33051.11010.18670.090*
C330.3880 (2)0.5807 (2)0.1593 (2)0.0621 (8)
H330.38740.60390.20980.075*
C340.3651 (2)0.4894 (3)0.1449 (3)0.0725 (10)
H340.35090.45240.18550.087*
C350.3637 (2)0.4550 (3)0.0712 (3)0.0726 (10)
H350.34770.39440.06110.087*
C360.3863 (2)0.5104 (2)0.0104 (2)0.0625 (9)
C370.3880 (2)0.4803 (3)0.0691 (3)0.0794 (12)
H370.37160.42070.08300.095*
C380.4129 (3)0.5371 (3)0.1234 (3)0.0816 (12)
H380.41300.51570.17450.098*
C390.4390 (2)0.6287 (3)0.1058 (2)0.0690 (10)
C400.4692 (3)0.6887 (4)0.1596 (2)0.0883 (14)
H400.47310.66960.21070.106*
C410.4930 (3)0.7753 (4)0.1366 (3)0.0898 (15)
H410.51350.81550.17200.108*
C420.4863 (2)0.8031 (3)0.0601 (2)0.0728 (10)
H420.50160.86280.04560.087*
C430.43604 (18)0.6620 (2)0.02923 (18)0.0525 (7)
C440.40974 (17)0.6017 (2)0.02984 (18)0.0486 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0580 (2)0.0468 (2)0.0536 (2)0.00002 (15)0.00018 (17)0.00421 (16)
S10.0571 (5)0.0653 (5)0.0581 (5)0.0045 (4)0.0014 (4)0.0148 (4)
S20.0494 (4)0.0664 (5)0.0614 (5)0.0048 (4)0.0010 (4)0.0096 (4)
S30.0610 (5)0.0534 (5)0.0898 (7)0.0001 (4)0.0067 (5)0.0041 (5)
S40.0629 (5)0.0519 (5)0.0657 (5)0.0007 (4)0.0082 (4)0.0078 (4)
N10.0489 (14)0.0607 (17)0.0551 (15)0.0023 (12)0.0001 (12)0.0111 (12)
N20.0642 (16)0.0549 (15)0.0533 (15)0.0067 (13)0.0033 (12)0.0009 (12)
N30.0543 (14)0.0599 (16)0.0518 (15)0.0003 (13)0.0029 (12)0.0055 (13)
N40.0557 (14)0.0428 (13)0.0490 (14)0.0008 (11)0.0073 (11)0.0019 (11)
C10.0513 (16)0.0419 (16)0.0604 (19)0.0001 (12)0.0037 (14)0.0103 (13)
C20.0492 (16)0.059 (2)0.066 (2)0.0035 (14)0.0030 (15)0.0088 (16)
C30.0407 (14)0.0590 (19)0.0592 (18)0.0035 (13)0.0008 (13)0.0049 (15)
C40.080 (2)0.079 (3)0.062 (2)0.018 (2)0.0058 (18)0.0100 (19)
C50.107 (3)0.093 (3)0.097 (3)0.033 (3)0.011 (3)0.028 (3)
C60.078 (3)0.058 (2)0.131 (4)0.011 (2)0.008 (3)0.004 (3)
C70.070 (2)0.086 (3)0.097 (3)0.010 (2)0.011 (2)0.034 (3)
C80.060 (2)0.089 (3)0.065 (2)0.0057 (19)0.0032 (17)0.003 (2)
C90.0608 (18)0.0516 (18)0.0596 (19)0.0034 (14)0.0007 (15)0.0028 (15)
C100.089 (3)0.059 (2)0.064 (2)0.0055 (19)0.0059 (19)0.0022 (17)
C110.074 (2)0.0536 (18)0.0574 (19)0.0016 (16)0.0024 (16)0.0027 (15)
C120.086 (3)0.099 (3)0.062 (2)0.015 (2)0.005 (2)0.008 (2)
C130.153 (5)0.100 (4)0.053 (2)0.022 (3)0.003 (3)0.005 (2)
C140.165 (5)0.077 (3)0.072 (3)0.016 (3)0.050 (3)0.000 (2)
C150.103 (4)0.104 (4)0.120 (4)0.006 (3)0.051 (4)0.001 (3)
C160.078 (3)0.098 (3)0.096 (3)0.004 (2)0.011 (2)0.016 (3)
C170.0644 (18)0.0510 (17)0.0501 (17)0.0059 (15)0.0098 (14)0.0010 (14)
C180.0623 (19)0.065 (2)0.0545 (19)0.0067 (16)0.0006 (15)0.0010 (16)
C190.074 (2)0.085 (3)0.054 (2)0.005 (2)0.0047 (17)0.0108 (18)
C200.0639 (19)0.068 (2)0.0490 (17)0.0059 (17)0.0014 (14)0.0074 (16)
C210.083 (3)0.073 (3)0.071 (2)0.005 (2)0.002 (2)0.003 (2)
C220.091 (3)0.101 (3)0.075 (3)0.026 (3)0.009 (2)0.010 (2)
C230.066 (2)0.167 (6)0.055 (2)0.001 (3)0.0039 (19)0.016 (3)
C240.074 (3)0.123 (4)0.063 (2)0.030 (3)0.004 (2)0.005 (3)
C250.073 (2)0.074 (2)0.064 (2)0.0131 (19)0.0002 (18)0.0025 (19)
C260.081 (2)0.0561 (19)0.0562 (19)0.0052 (17)0.0066 (17)0.0082 (16)
C270.0578 (18)0.0548 (19)0.064 (2)0.0002 (15)0.0053 (15)0.0006 (16)
C280.073 (2)0.060 (2)0.080 (3)0.0028 (18)0.0090 (19)0.0021 (19)
C290.074 (2)0.057 (2)0.121 (4)0.0095 (19)0.008 (3)0.010 (2)
C300.075 (2)0.070 (3)0.092 (3)0.012 (2)0.018 (2)0.023 (2)
C310.088 (3)0.082 (3)0.073 (3)0.010 (2)0.012 (2)0.020 (2)
C320.086 (3)0.072 (2)0.064 (2)0.010 (2)0.0000 (19)0.0037 (19)
C330.071 (2)0.0561 (19)0.0590 (19)0.0010 (16)0.0060 (16)0.0014 (16)
C340.072 (2)0.055 (2)0.091 (3)0.0109 (17)0.010 (2)0.010 (2)
C350.062 (2)0.0501 (19)0.104 (3)0.0102 (16)0.000 (2)0.010 (2)
C360.0527 (17)0.0552 (19)0.077 (2)0.0012 (15)0.0032 (16)0.0199 (18)
C370.068 (2)0.077 (3)0.089 (3)0.006 (2)0.008 (2)0.044 (2)
C380.079 (3)0.100 (3)0.063 (2)0.015 (2)0.004 (2)0.037 (2)
C390.0568 (19)0.098 (3)0.0502 (19)0.0176 (19)0.0021 (15)0.0117 (19)
C400.077 (3)0.139 (4)0.049 (2)0.025 (3)0.0095 (19)0.001 (3)
C410.078 (3)0.129 (5)0.065 (3)0.008 (3)0.019 (2)0.029 (3)
C420.065 (2)0.082 (3)0.072 (2)0.0064 (19)0.0103 (18)0.020 (2)
C430.0453 (15)0.0644 (19)0.0468 (16)0.0036 (14)0.0005 (12)0.0076 (15)
C440.0427 (14)0.0475 (16)0.0536 (17)0.0002 (12)0.0029 (12)0.0077 (13)
Geometric parameters (Å, º) top
Zn1—N32.205 (3)C18—C191.519 (5)
Zn1—N42.209 (2)C18—H18A0.9700
Zn1—S22.5043 (10)C18—H18B0.9700
Zn1—S32.5103 (11)C19—C201.504 (5)
Zn1—S12.5394 (10)C19—H19A0.9700
Zn1—S42.5522 (10)C19—H19B0.9700
S1—C11.725 (3)C20—C251.387 (5)
S2—C11.712 (3)C20—C211.395 (6)
S3—C171.721 (4)C21—C221.386 (6)
S4—C171.719 (3)C21—H210.9300
N1—C11.349 (4)C22—C231.373 (7)
N1—C21.476 (4)C22—H220.9300
N1—C91.482 (4)C23—C241.358 (7)
N2—C171.347 (4)C23—H230.9300
N2—C181.475 (4)C24—C251.366 (6)
N2—C261.478 (4)C24—H240.9300
N3—C421.326 (4)C25—H250.9300
N3—C431.353 (4)C26—C271.518 (5)
N4—C331.327 (4)C26—H26A0.9700
N4—C441.361 (4)C26—H26B0.9700
C2—C31.512 (5)C27—C281.371 (5)
C2—H2A0.9700C27—C321.383 (5)
C2—H2B0.9700C28—C291.407 (6)
C3—C41.369 (5)C28—H280.9300
C3—C81.391 (5)C29—C301.363 (6)
C4—C51.377 (6)C29—H290.9300
C4—H40.9300C30—C311.354 (6)
C5—C61.369 (7)C30—H300.9300
C5—H50.9300C31—C321.380 (5)
C6—C71.357 (6)C31—H310.9300
C6—H60.9300C32—H320.9300
C7—C81.387 (6)C33—C341.394 (5)
C7—H70.9300C33—H330.9300
C8—H80.9300C34—C351.359 (6)
C9—C101.519 (5)C34—H340.9300
C9—H9A0.9700C35—C361.399 (5)
C9—H9B0.9700C35—H350.9300
C10—C111.520 (5)C36—C441.413 (4)
C10—H10A0.9700C36—C371.435 (5)
C10—H10B0.9700C37—C381.342 (6)
C11—C121.371 (5)C37—H370.9300
C11—C161.382 (6)C38—C391.421 (6)
C12—C131.375 (6)C38—H380.9300
C12—H120.9300C39—C401.398 (6)
C13—C141.352 (8)C39—C431.407 (4)
C13—H130.9300C40—C411.363 (7)
C14—C151.364 (8)C40—H400.9300
C14—H140.9300C41—C421.389 (6)
C15—C161.368 (7)C41—H410.9300
C15—H150.9300C42—H420.9300
C16—H160.9300C43—C441.441 (5)
N3—Zn1—N475.10 (10)N2—C18—C19111.9 (3)
N3—Zn1—S2157.24 (8)N2—C18—H18A109.2
N4—Zn1—S295.51 (7)C19—C18—H18A109.2
N3—Zn1—S394.60 (8)N2—C18—H18B109.2
N4—Zn1—S3155.83 (7)C19—C18—H18B109.2
S2—Zn1—S3101.29 (3)H18A—C18—H18B107.9
N3—Zn1—S189.63 (7)C20—C19—C18113.4 (3)
N4—Zn1—S199.92 (7)C20—C19—H19A108.9
S2—Zn1—S171.32 (3)C18—C19—H19A108.9
S3—Zn1—S1101.84 (3)C20—C19—H19B108.9
N3—Zn1—S495.62 (7)C18—C19—H19B108.9
N4—Zn1—S487.89 (7)H19A—C19—H19B107.7
S2—Zn1—S4104.85 (3)C25—C20—C21117.5 (4)
S3—Zn1—S471.16 (3)C25—C20—C19121.5 (4)
S1—Zn1—S4171.52 (3)C21—C20—C19121.0 (3)
C1—S1—Zn184.82 (11)C22—C21—C20120.2 (4)
C1—S2—Zn186.19 (12)C22—C21—H21119.9
C17—S3—Zn186.12 (11)C20—C21—H21119.9
C17—S4—Zn184.84 (12)C23—C22—C21120.4 (5)
C1—N1—C2122.4 (3)C23—C22—H22119.8
C1—N1—C9121.7 (3)C21—C22—H22119.8
C2—N1—C9115.6 (3)C24—C23—C22119.7 (4)
C17—N2—C18121.6 (3)C24—C23—H23120.1
C17—N2—C26122.3 (3)C22—C23—H23120.1
C18—N2—C26116.2 (3)C23—C24—C25120.6 (4)
C42—N3—C43117.7 (3)C23—C24—H24119.7
C42—N3—Zn1127.1 (3)C25—C24—H24119.7
C43—N3—Zn1115.1 (2)C24—C25—C20121.5 (4)
C33—N4—C44118.3 (3)C24—C25—H25119.2
C33—N4—Zn1126.9 (2)C20—C25—H25119.2
C44—N4—Zn1114.61 (19)N2—C26—C27113.7 (3)
N1—C1—S2121.0 (3)N2—C26—H26A108.8
N1—C1—S1121.3 (2)C27—C26—H26A108.8
S2—C1—S1117.67 (19)N2—C26—H26B108.8
N1—C2—C3113.6 (3)C27—C26—H26B108.8
N1—C2—H2A108.8H26A—C26—H26B107.7
C3—C2—H2A108.8C28—C27—C32119.1 (4)
N1—C2—H2B108.8C28—C27—C26120.0 (3)
C3—C2—H2B108.8C32—C27—C26120.8 (3)
H2A—C2—H2B107.7C27—C28—C29119.5 (4)
C4—C3—C8118.3 (3)C27—C28—H28120.2
C4—C3—C2120.1 (3)C29—C28—H28120.2
C8—C3—C2121.6 (3)C30—C29—C28120.2 (4)
C3—C4—C5120.8 (4)C30—C29—H29119.9
C3—C4—H4119.6C28—C29—H29119.9
C5—C4—H4119.6C31—C30—C29120.2 (4)
C6—C5—C4120.6 (4)C31—C30—H30119.9
C6—C5—H5119.7C29—C30—H30119.9
C4—C5—H5119.7C30—C31—C32120.4 (4)
C7—C6—C5119.6 (4)C30—C31—H31119.8
C7—C6—H6120.2C32—C31—H31119.8
C5—C6—H6120.2C31—C32—C27120.5 (4)
C6—C7—C8120.4 (4)C31—C32—H32119.7
C6—C7—H7119.8C27—C32—H32119.7
C8—C7—H7119.8N4—C33—C34122.5 (3)
C7—C8—C3120.3 (4)N4—C33—H33118.7
C7—C8—H8119.8C34—C33—H33118.7
C3—C8—H8119.8C35—C34—C33119.5 (4)
N1—C9—C10109.9 (3)C35—C34—H34120.2
N1—C9—H9A109.7C33—C34—H34120.2
C10—C9—H9A109.7C34—C35—C36120.2 (3)
N1—C9—H9B109.7C34—C35—H35119.9
C10—C9—H9B109.7C36—C35—H35119.9
H9A—C9—H9B108.2C35—C36—C44116.9 (3)
C9—C10—C11113.8 (3)C35—C36—C37124.5 (4)
C9—C10—H10A108.8C44—C36—C37118.6 (4)
C11—C10—H10A108.8C38—C37—C36120.7 (4)
C9—C10—H10B108.8C38—C37—H37119.6
C11—C10—H10B108.8C36—C37—H37119.6
H10A—C10—H10B107.7C37—C38—C39122.4 (4)
C12—C11—C16118.3 (4)C37—C38—H38118.8
C12—C11—C10121.1 (4)C39—C38—H38118.8
C16—C11—C10120.5 (4)C40—C39—C43116.8 (4)
C11—C12—C13120.3 (5)C40—C39—C38124.4 (4)
C11—C12—H12119.8C43—C39—C38118.8 (4)
C13—C12—H12119.8C41—C40—C39119.8 (4)
C14—C13—C12120.8 (5)C41—C40—H40120.1
C14—C13—H13119.6C39—C40—H40120.1
C12—C13—H13119.6C40—C41—C42119.5 (4)
C13—C14—C15119.6 (4)C40—C41—H41120.2
C13—C14—H14120.2C42—C41—H41120.2
C15—C14—H14120.2N3—C42—C41122.9 (4)
C14—C15—C16120.3 (5)N3—C42—H42118.6
C14—C15—H15119.8C41—C42—H42118.6
C16—C15—H15119.8N3—C43—C39123.2 (3)
C15—C16—C11120.6 (5)N3—C43—C44117.4 (3)
C15—C16—H16119.7C39—C43—C44119.4 (3)
C11—C16—H16119.7N4—C44—C36122.5 (3)
N2—C17—S4120.2 (3)N4—C44—C43117.5 (3)
N2—C17—S3121.9 (3)C36—C44—C43120.0 (3)
S4—C17—S3117.83 (19)
C2—N1—C1—S2173.1 (2)C21—C20—C25—C241.4 (5)
C9—N1—C1—S20.4 (4)C19—C20—C25—C24176.4 (4)
C2—N1—C1—S15.0 (4)C17—N2—C26—C27114.4 (4)
C9—N1—C1—S1178.5 (2)C18—N2—C26—C2766.2 (4)
Zn1—S2—C1—N1177.3 (3)N2—C26—C27—C28122.9 (4)
Zn1—S2—C1—S10.82 (16)N2—C26—C27—C3256.6 (5)
Zn1—S1—C1—N1177.3 (3)C32—C27—C28—C290.6 (6)
Zn1—S1—C1—S20.81 (16)C26—C27—C28—C29180.0 (4)
C1—N1—C2—C392.6 (4)C27—C28—C29—C301.2 (6)
C9—N1—C2—C393.6 (3)C28—C29—C30—C311.5 (7)
N1—C2—C3—C4100.2 (4)C29—C30—C31—C321.1 (7)
N1—C2—C3—C882.0 (4)C30—C31—C32—C270.5 (6)
C8—C3—C4—C50.2 (6)C28—C27—C32—C310.2 (6)
C2—C3—C4—C5177.6 (4)C26—C27—C32—C31179.7 (4)
C3—C4—C5—C60.0 (7)C44—N4—C33—C341.1 (5)
C4—C5—C6—C70.7 (8)Zn1—N4—C33—C34177.3 (3)
C5—C6—C7—C81.1 (7)N4—C33—C34—C351.5 (6)
C6—C7—C8—C30.9 (6)C33—C34—C35—C360.9 (6)
C4—C3—C8—C70.2 (5)C34—C35—C36—C440.1 (5)
C2—C3—C8—C7178.0 (3)C34—C35—C36—C37179.1 (4)
C1—N1—C9—C1092.1 (4)C35—C36—C37—C38177.9 (4)
C2—N1—C9—C1081.8 (4)C44—C36—C37—C381.3 (5)
N1—C9—C10—C11176.4 (3)C36—C37—C38—C390.3 (6)
C9—C10—C11—C12114.3 (4)C37—C38—C39—C40176.8 (4)
C9—C10—C11—C1669.7 (5)C37—C38—C39—C432.2 (6)
C16—C11—C12—C132.8 (7)C43—C39—C40—C410.9 (6)
C10—C11—C12—C13173.3 (4)C38—C39—C40—C41179.8 (4)
C11—C12—C13—C142.0 (8)C39—C40—C41—C420.4 (7)
C12—C13—C14—C150.0 (8)C43—N3—C42—C410.7 (5)
C13—C14—C15—C161.3 (9)Zn1—N3—C42—C41179.2 (3)
C14—C15—C16—C110.5 (8)C40—C41—C42—N31.3 (7)
C12—C11—C16—C151.5 (7)C42—N3—C43—C390.8 (5)
C10—C11—C16—C15174.6 (4)Zn1—N3—C43—C39177.9 (2)
C18—N2—C17—S48.2 (4)C42—N3—C43—C44177.5 (3)
C26—N2—C17—S4171.1 (2)Zn1—N3—C43—C443.8 (3)
C18—N2—C17—S3172.5 (2)C40—C39—C43—N31.5 (5)
C26—N2—C17—S38.3 (4)C38—C39—C43—N3179.5 (3)
Zn1—S4—C17—N2177.3 (3)C40—C39—C43—C44176.7 (3)
Zn1—S4—C17—S32.12 (17)C38—C39—C43—C442.3 (5)
Zn1—S3—C17—N2177.2 (3)C33—N4—C44—C360.3 (4)
Zn1—S3—C17—S42.15 (17)Zn1—N4—C44—C36176.9 (2)
C17—N2—C18—C1977.9 (4)C33—N4—C44—C43178.8 (3)
C26—N2—C18—C19102.8 (4)Zn1—N4—C44—C434.6 (3)
N2—C18—C19—C20178.0 (3)C35—C36—C44—N40.2 (5)
C18—C19—C20—C25107.5 (4)C37—C36—C44—N4179.5 (3)
C18—C19—C20—C2174.8 (5)C35—C36—C44—C43178.2 (3)
C25—C20—C21—C220.5 (6)C37—C36—C44—C431.1 (5)
C19—C20—C21—C22177.3 (4)N3—C43—C44—N40.5 (4)
C20—C21—C22—C231.2 (6)C39—C43—C44—N4177.8 (3)
C21—C22—C23—C242.0 (7)N3—C43—C44—C36179.1 (3)
C22—C23—C24—C251.1 (7)C39—C43—C44—C360.8 (4)
C23—C24—C25—C200.6 (6)
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the N1/C33–C36/C44 ring.
D—H···AD—HH···AD···AD—H···A
C2—H2B···S10.972.633.046 (4)106
C9—H9B···S20.972.593.016 (4)107
C18—H18A···S40.972.653.000 (4)102
C26—H26B···S30.972.533.060 (4)115
C12—H12···Cgi0.932.893.777 (5)160
Symmetry code: (i) x3/2, y1/2, z3/2.
 

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