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Both zinc di­thio­carbamates and sterically hindered phenols are known to exhibit antioxidant activity. As part of an investigation on the effect of both moieties being combined in one mol­ecule, the title compound, [Zn(C17H26NOS2)2], has been prepared and its crystal structure determined.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803007372/bt6255sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803007372/bt6255Isup2.hkl
Contains datablock I

CCDC reference: 214559

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.038
  • wR factor = 0.101
  • Data-to-parameter ratio = 16.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
WEIGH_01 Alert C Extra text has been found in the _refine_ls_weighting_scheme field. This should be in the _refine_ls_weighting_details field. Weighting scheme given as calc w = 1/[\s^2^(Fo^2^)+(0.0517P)^2^+0.948 Weighting scheme identified as calc PLAT_731 Alert C Bond Calc 0.85(3), Rep 0.846(10) .... 3.00 su-Ratio O1A -H51 1.555 1.555
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check

Comment top

Zinc dithiocarbamates have been investigated as antioxidant additives to plastics (Al-Malaika et al., 1986) and hydrocarbon-based lubricants (Shelkova et al., 1990) and their mechanism of action received some attention. In an investigation to optimize antioxidant efficiency of additives to vegetable oils to be utilized as lubricants the zinc dithiocarbamate moiety was combined with a sterically hindered phenol (Becker & Knorr, 1996; Becker, Knorr & Kelm, 1996). The preparation followed a known pathway for insertion of CS2 into 4-hydroxyphenylmethylamines (Fitton at al., 1969) with subsequent alkaline hydrolysis and teatment of the dithiocarbamic acid with ZnSO4. Due to the voluminous groups in ortho positions the phenolic hydroxy groups do not form hydrogen bonds.

Experimental top

A solution of bis(3,5-di-tert-butyl-2-hydroxybenzyl)-n-butylamine in ethanol was treated with sodium hydroxide solution and excess CS2 and stirred for 2 h at ambient temperature. After addition of water, a yellow oil could be separated with diethyl ether. The diethyl ether solution was stirred for 3 h with aqueous ZnSO4. The precipitate formed after evaporaion of organic solvent was recrystallized from n-hexane/ethanol to yield colourless crystals, m.p. 436 K. IR (cm−1): 3300, 2970, 2935, 1475, 1425, 1385, 1355, 1335, 1290, 1235, 1210, 1195, 1160, 1125, 1095, 1085, 965, 925, 875, 855, 810, 790, 760, 735, 715, 675, 640.

Refinement top

The hydroxyl H atoms were refined freely and all other H atoms were refined as riding.

Computing details top

Data collection: CAD-4 (Enraf-Nonius, 1977); cell refinement: CAD-4; data reduction: PROCESS in MolEN (Fair, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1999); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids (SHELXTL; Sheldrick, 1999). H atoms have been omitted for clarity.
Bis[N-n-butyl-N-(3,5-di-tert-butyl-2-hydroxybenzyl)dithiocarbamato- κ2S,S']zinc(II) top
Crystal data top
[Zn(C17H26NOS2)2]Z = 2
Mr = 714.39F(000) = 760
Triclinic, P1Dx = 1.273 Mg m3
a = 8.936 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.762 (2) ÅCell parameters from 25 reflections
c = 19.740 (3) Åθ = 12–20°
α = 80.63 (1)°µ = 0.91 mm1
β = 88.39 (2)°T = 293 K
γ = 84.11 (2)°Prismatic, colourless
V = 1863.0 (8) Å30.35 × 0.28 × 0.25 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
5755 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.008
Graphite monochromatorθmax = 25.0°, θmin = 1.9°
2θω scansh = 010
Absorption correction: ψ scan
(North et al., 1968)
k = 1212
Tmin = 0.683, Tmax = 0.796l = 2323
6539 measured reflections3 standard reflections every 120 min
6517 independent reflections intensity decay: 1.5%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.101Calculated w = 1/[σ2(Fo2) + (0.0517P)2 + 0.9487P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
6517 reflectionsΔρmax = 0.37 e Å3
397 parametersΔρmin = 0.44 e Å3
118 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0021 (5)
Crystal data top
[Zn(C17H26NOS2)2]γ = 84.11 (2)°
Mr = 714.39V = 1863.0 (8) Å3
Triclinic, P1Z = 2
a = 8.936 (3) ÅMo Kα radiation
b = 10.762 (2) ŵ = 0.91 mm1
c = 19.740 (3) ÅT = 293 K
α = 80.63 (1)°0.35 × 0.28 × 0.25 mm
β = 88.39 (2)°
Data collection top
Enraf-Nonius CAD-4
diffractometer
5755 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.008
Tmin = 0.683, Tmax = 0.7963 standard reflections every 120 min
6539 measured reflections intensity decay: 1.5%
6517 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.038118 restraints
wR(F2) = 0.101H atoms treated by a mixture of independent and constrained refinement
S = 1.07Δρmax = 0.37 e Å3
6517 reflectionsΔρmin = 0.44 e Å3
397 parameters
Special details top

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Zn0.18643 (3)0.78001 (3)0.047980 (14)0.05466 (12)
S1A0.13501 (7)0.78407 (6)0.16598 (3)0.05060 (16)
S2A0.02705 (9)0.62218 (7)0.07508 (3)0.0619 (2)
O1A0.24499 (19)0.52297 (19)0.28275 (9)0.0594 (5)
N1A0.0495 (2)0.60536 (17)0.20710 (9)0.0433 (4)
C1A0.0039 (2)0.5404 (2)0.33196 (11)0.0411 (5)
C2A0.1429 (2)0.4836 (2)0.33291 (10)0.0427 (5)
C3A0.1924 (3)0.3836 (2)0.38413 (11)0.0443 (5)
C4A0.0885 (3)0.3488 (2)0.43597 (11)0.0466 (5)
H10.11910.28360.47130.056*
C5A0.0566 (3)0.4051 (2)0.43806 (11)0.0443 (5)
C6A0.1021 (3)0.5002 (2)0.38519 (11)0.0438 (5)
H20.20030.53830.38500.053*
C7A0.0598 (3)0.6442 (2)0.27526 (11)0.0460 (5)
H30.16390.67200.28480.055*
H40.00160.71570.27480.055*
C8A0.0277 (3)0.6636 (2)0.15531 (11)0.0425 (5)
C9A0.1378 (3)0.5005 (2)0.19823 (13)0.0501 (6)
H50.14570.44540.24200.060*
H60.08510.45120.16630.060*
C10A0.2942 (3)0.5469 (3)0.17167 (17)0.0655 (7)
H70.34890.59070.20540.079*
H80.28590.60760.13000.079*
C11A0.3825 (4)0.4446 (3)0.1568 (2)0.0844 (10)
H90.32440.39660.12580.101*
H100.39780.38750.19920.101*
C12A0.5314 (4)0.4917 (3)0.1257 (2)0.1028 (13)
H110.58170.42140.11690.123*
H120.51740.54760.08340.123*
H130.59130.53670.15680.123*
C13A0.3514 (3)0.3152 (3)0.38312 (13)0.0558 (6)
C14A0.3742 (3)0.2542 (3)0.31875 (16)0.0689 (7)
H140.30010.19600.31780.083*
H150.47290.20950.31900.083*
H160.36410.31850.27890.083*
C15A0.4705 (3)0.4069 (4)0.38605 (19)0.0797 (9)
H170.45820.47460.34780.096*
H180.56900.36260.38400.096*
H190.45890.44090.42810.096*
C16A0.3757 (4)0.2091 (4)0.44475 (18)0.0927 (11)
H200.30320.14940.44400.111*
H210.36390.24440.48650.111*
H220.47530.16700.44240.111*
C17A0.1615 (3)0.3630 (3)0.49651 (12)0.0571 (6)
H230.25780.41130.48940.069*
H240.12050.37600.53890.069*
H250.17310.27470.49850.069*
S1B0.42852 (7)0.78399 (6)0.00006 (3)0.05168 (17)
S2B0.15922 (6)0.96083 (6)0.03641 (3)0.05032 (16)
O1B0.14910 (19)0.97115 (17)0.20215 (8)0.0516 (4)
N1B0.42762 (19)0.98616 (16)0.09759 (9)0.0384 (4)
C1B0.3598 (2)1.0957 (2)0.21509 (11)0.0396 (5)
C2B0.2536 (2)1.03269 (19)0.24255 (11)0.0388 (5)
C3B0.2507 (2)1.0278 (2)0.31290 (11)0.0396 (5)
C4B0.3596 (3)1.0871 (2)0.35363 (11)0.0473 (5)
H260.36081.08390.40040.057*
C5B0.4683 (3)1.1519 (2)0.32792 (12)0.0501 (6)
C6B0.4653 (3)1.1555 (2)0.25899 (12)0.0461 (5)
H270.53541.19880.24090.055*
C7B0.3633 (3)1.1038 (2)0.13974 (11)0.0423 (5)
H280.42191.17200.13340.051*
H290.26151.12440.12380.051*
C8B0.3484 (2)0.9183 (2)0.05065 (10)0.0385 (5)
C9B0.5908 (2)0.9535 (2)0.10700 (12)0.0454 (5)
H300.63500.92100.06250.055*
H310.63661.02990.12560.055*
C10B0.6276 (3)0.8570 (3)0.15376 (13)0.0569 (6)
H320.58910.89070.19920.068*
H330.57900.78140.13650.068*
C11B0.7977 (3)0.8228 (4)0.15838 (17)0.0805 (9)
H340.81800.77200.19450.097*
H350.84540.90030.17170.097*
C12B0.8670 (4)0.7542 (4)0.0956 (2)0.0976 (12)
H360.97300.73630.10330.117*
H370.82240.67630.08230.117*
H380.85120.80490.05970.117*
C13B0.1301 (3)0.9610 (2)0.34360 (12)0.0470 (5)
C14B0.1359 (3)0.8221 (2)0.31077 (15)0.0613 (7)
H390.06010.78250.33050.074*
H400.11810.81630.26220.074*
H410.23320.78010.31890.074*
C15B0.0251 (3)1.0287 (3)0.33246 (15)0.0625 (7)
H420.02731.11610.35300.075*
H430.04581.02290.28410.075*
H440.09990.98960.35330.075*
C16B0.1525 (4)0.9658 (3)0.42087 (14)0.0697 (8)
H450.14971.05240.44290.084*
H460.07380.92620.43860.084*
H470.24810.92170.42980.084*
C17B0.5842 (3)1.2135 (3)0.37498 (15)0.0747 (9)
H480.56871.19990.42100.090*
H490.68291.17710.36040.090*
H500.57491.30270.37360.090*
H510.205 (4)0.590 (2)0.2584 (15)0.089 (12)*
H520.150 (4)0.981 (3)0.1608 (7)0.086 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn0.0602 (2)0.0636 (2)0.03891 (17)0.02071 (14)0.00768 (12)0.00313 (13)
S1A0.0630 (4)0.0513 (3)0.0395 (3)0.0252 (3)0.0044 (3)0.0018 (2)
S2A0.0820 (5)0.0693 (4)0.0395 (3)0.0353 (4)0.0035 (3)0.0072 (3)
O1A0.0434 (9)0.0785 (13)0.0482 (10)0.0085 (9)0.0107 (8)0.0131 (9)
N1A0.0502 (11)0.0407 (10)0.0374 (9)0.0128 (8)0.0016 (8)0.0038 (8)
C1A0.0438 (12)0.0464 (12)0.0332 (10)0.0121 (9)0.0030 (9)0.0023 (9)
C2A0.0419 (12)0.0562 (13)0.0298 (10)0.0150 (10)0.0049 (9)0.0008 (9)
C3A0.0439 (12)0.0558 (13)0.0335 (11)0.0099 (10)0.0031 (9)0.0040 (9)
C4A0.0536 (13)0.0541 (13)0.0312 (11)0.0155 (11)0.0040 (9)0.0029 (9)
C5A0.0506 (13)0.0546 (13)0.0303 (10)0.0200 (10)0.0040 (9)0.0056 (9)
C6A0.0410 (12)0.0534 (13)0.0377 (11)0.0118 (10)0.0043 (9)0.0058 (10)
C7A0.0502 (13)0.0449 (12)0.0409 (12)0.0072 (10)0.0067 (10)0.0005 (9)
C8A0.0474 (12)0.0393 (11)0.0387 (11)0.0097 (9)0.0031 (9)0.0038 (9)
C9A0.0594 (14)0.0417 (12)0.0479 (13)0.0184 (10)0.0007 (11)0.0053 (10)
C10A0.0619 (16)0.0521 (15)0.082 (2)0.0156 (12)0.0024 (14)0.0033 (14)
C11A0.073 (2)0.0599 (17)0.118 (3)0.0246 (15)0.0251 (19)0.0067 (17)
C12A0.085 (2)0.067 (2)0.152 (4)0.0225 (18)0.036 (2)0.010 (2)
C13A0.0467 (13)0.0702 (16)0.0470 (13)0.0011 (12)0.0054 (11)0.0012 (12)
C14A0.0583 (16)0.0737 (18)0.0740 (18)0.0001 (14)0.0057 (14)0.0149 (15)
C15A0.0467 (15)0.103 (2)0.093 (2)0.0083 (15)0.0136 (15)0.0243 (19)
C16A0.075 (2)0.110 (3)0.074 (2)0.0233 (19)0.0068 (17)0.0229 (19)
C17A0.0608 (15)0.0730 (17)0.0384 (12)0.0259 (13)0.0104 (11)0.0011 (11)
S1B0.0528 (3)0.0509 (3)0.0440 (3)0.0021 (3)0.0049 (3)0.0087 (3)
S2B0.0386 (3)0.0663 (4)0.0402 (3)0.0002 (3)0.0055 (2)0.0048 (3)
O1B0.0513 (10)0.0674 (11)0.0390 (9)0.0290 (8)0.0077 (7)0.0036 (8)
N1B0.0371 (9)0.0419 (9)0.0344 (9)0.0070 (7)0.0002 (7)0.0004 (7)
C1B0.0411 (11)0.0373 (11)0.0377 (11)0.0056 (9)0.0027 (9)0.0038 (9)
C2B0.0373 (11)0.0374 (11)0.0383 (11)0.0055 (8)0.0018 (9)0.0042 (9)
C3B0.0415 (11)0.0377 (11)0.0373 (11)0.0051 (9)0.0021 (9)0.0020 (9)
C4B0.0515 (13)0.0536 (13)0.0331 (11)0.0084 (10)0.0016 (9)0.0053 (10)
C5B0.0464 (13)0.0562 (14)0.0434 (12)0.0146 (11)0.0023 (10)0.0101 (10)
C6B0.0433 (12)0.0463 (12)0.0467 (12)0.0157 (10)0.0050 (10)0.0068 (10)
C7B0.0479 (12)0.0383 (11)0.0395 (11)0.0093 (9)0.0024 (9)0.0008 (9)
C8B0.0415 (11)0.0441 (11)0.0293 (10)0.0044 (9)0.0001 (8)0.0036 (8)
C9B0.0418 (12)0.0504 (13)0.0431 (12)0.0127 (10)0.0007 (9)0.0002 (10)
C10B0.0537 (14)0.0690 (16)0.0484 (14)0.0018 (12)0.0017 (11)0.0130 (12)
C11B0.0616 (18)0.100 (2)0.079 (2)0.0047 (17)0.0140 (15)0.0205 (18)
C12B0.072 (2)0.102 (3)0.122 (3)0.0200 (19)0.035 (2)0.039 (2)
C13B0.0503 (13)0.0492 (13)0.0419 (12)0.0112 (10)0.0044 (10)0.0045 (10)
C14B0.0704 (17)0.0487 (14)0.0672 (17)0.0160 (12)0.0054 (13)0.0096 (12)
C15B0.0488 (14)0.0686 (17)0.0708 (17)0.0101 (12)0.0126 (13)0.0091 (14)
C16B0.081 (2)0.087 (2)0.0466 (14)0.0271 (16)0.0089 (13)0.0134 (14)
C17B0.0660 (18)0.097 (2)0.0587 (17)0.0364 (16)0.0106 (14)0.0109 (15)
Geometric parameters (Å, º) top
Zn—S2A2.3147 (9)C17A—H240.9600
Zn—S1B2.3382 (10)C17A—H250.9600
Zn—S2B2.3433 (8)S1B—C8B1.720 (2)
Zn—S1A2.3680 (7)S2B—C8B1.733 (2)
S1A—C8A1.732 (2)O1B—C2B1.364 (3)
S2A—C8A1.714 (2)O1B—H520.840 (10)
O1A—C2A1.373 (3)N1B—C8B1.320 (3)
O1A—H510.846 (10)N1B—C7B1.469 (3)
N1A—C8A1.324 (3)N1B—C9B1.479 (3)
N1A—C7A1.471 (3)C1B—C2B1.391 (3)
N1A—C9A1.477 (3)C1B—C6B1.396 (3)
C1A—C2A1.389 (3)C1B—C7B1.505 (3)
C1A—C6A1.393 (3)C2B—C3B1.399 (3)
C1A—C7A1.504 (3)C3B—C4B1.385 (3)
C2A—C3A1.396 (3)C3B—C13B1.543 (3)
C3A—C4A1.394 (3)C4B—C5B1.403 (3)
C3A—C13A1.532 (3)C4B—H260.9300
C4A—C5A1.376 (3)C5B—C6B1.367 (3)
C4A—H10.9300C5B—C17B1.504 (3)
C5A—C6A1.375 (3)C6B—H270.9300
C5A—C17A1.507 (3)C7B—H280.9700
C6A—H20.9300C7B—H290.9700
C7A—H30.9700C9B—C10B1.504 (3)
C7A—H40.9700C9B—H300.9700
C9A—C10A1.514 (4)C9B—H310.9700
C9A—H50.9700C10B—C11B1.530 (4)
C9A—H60.9700C10B—H320.9700
C10A—C11A1.489 (4)C10B—H330.9700
C10A—H70.9700C11B—C12B1.455 (5)
C10A—H80.9700C11B—H340.9700
C11A—C12A1.486 (5)C11B—H350.9700
C11A—H90.9700C12B—H360.9600
C11A—H100.9700C12B—H370.9600
C12A—H110.9600C12B—H380.9600
C12A—H120.9600C13B—C14B1.526 (3)
C12A—H130.9600C13B—C16B1.526 (3)
C13A—C14A1.522 (4)C13B—C15B1.527 (4)
C13A—C16A1.530 (4)C14B—H390.9600
C13A—C15A1.532 (4)C14B—H400.9600
C14A—H140.9600C14B—H410.9600
C14A—H150.9600C15B—H420.9600
C14A—H160.9600C15B—H430.9600
C15A—H170.9600C15B—H440.9600
C15A—H180.9600C16B—H450.9600
C15A—H190.9600C16B—H460.9600
C16A—H200.9600C16B—H470.9600
C16A—H210.9600C17B—H480.9600
C16A—H220.9600C17B—H490.9600
C17A—H230.9600C17B—H500.9600
S2A—Zn—S1B133.24 (3)C5A—C17A—H25109.5
S2A—Zn—S2B128.80 (3)H23—C17A—H25109.5
S1B—Zn—S2B77.80 (3)H24—C17A—H25109.5
S2A—Zn—S1A77.78 (3)C8B—S1B—Zn82.94 (8)
S1B—Zn—S1A123.11 (3)C8B—S2B—Zn82.54 (8)
S2B—Zn—S1A123.28 (3)C2B—O1B—H52114 (2)
C8A—S1A—Zn81.55 (8)C8B—N1B—C7B122.63 (18)
C8A—S2A—Zn83.53 (8)C8B—N1B—C9B121.54 (18)
C2A—O1A—H51108 (2)C7B—N1B—C9B115.65 (17)
C8A—N1A—C7A122.86 (19)C2B—C1B—C6B119.0 (2)
C8A—N1A—C9A121.22 (19)C2B—C1B—C7B122.22 (19)
C7A—N1A—C9A115.84 (18)C6B—C1B—C7B118.8 (2)
C2A—C1A—C6A119.0 (2)O1B—C2B—C1B121.68 (19)
C2A—C1A—C7A121.94 (19)O1B—C2B—C3B116.86 (19)
C6A—C1A—C7A119.1 (2)C1B—C2B—C3B121.45 (19)
O1A—C2A—C1A121.0 (2)C4B—C3B—C2B116.8 (2)
O1A—C2A—C3A117.3 (2)C4B—C3B—C13B121.7 (2)
C1A—C2A—C3A121.70 (19)C2B—C3B—C13B121.43 (19)
C4A—C3A—C2A116.1 (2)C3B—C4B—C5B123.4 (2)
C4A—C3A—C13A121.9 (2)C3B—C4B—H26118.3
C2A—C3A—C13A122.0 (2)C5B—C4B—H26118.3
C5A—C4A—C3A124.0 (2)C6B—C5B—C4B117.6 (2)
C5A—C4A—H1118.0C6B—C5B—C17B121.8 (2)
C3A—C4A—H1118.0C4B—C5B—C17B120.6 (2)
C6A—C5A—C4A117.8 (2)C5B—C6B—C1B121.7 (2)
C6A—C5A—C17A121.5 (2)C5B—C6B—H27119.1
C4A—C5A—C17A120.7 (2)C1B—C6B—H27119.1
C5A—C6A—C1A121.3 (2)N1B—C7B—C1B113.36 (18)
C5A—C6A—H2119.4N1B—C7B—H28108.9
C1A—C6A—H2119.4C1B—C7B—H28108.9
N1A—C7A—C1A113.22 (18)N1B—C7B—H29108.9
N1A—C7A—H3108.9C1B—C7B—H29108.9
C1A—C7A—H3108.9H28—C7B—H29107.7
N1A—C7A—H4108.9N1B—C8B—S1B121.57 (16)
C1A—C7A—H4108.9N1B—C8B—S2B121.71 (16)
H3—C7A—H4107.7S1B—C8B—S2B116.73 (12)
N1A—C8A—S2A121.48 (17)N1B—C9B—C10B113.69 (19)
N1A—C8A—S1A121.38 (17)N1B—C9B—H30108.8
S2A—C8A—S1A117.14 (13)C10B—C9B—H30108.8
N1A—C9A—C10A112.4 (2)N1B—C9B—H31108.8
N1A—C9A—H5109.1C10B—C9B—H31108.8
C10A—C9A—H5109.1H30—C9B—H31107.7
N1A—C9A—H6109.1C9B—C10B—C11B110.9 (2)
C10A—C9A—H6109.1C9B—C10B—H32109.5
H5—C9A—H6107.8C11B—C10B—H32109.5
C11A—C10A—C9A114.0 (2)C9B—C10B—H33109.5
C11A—C10A—H7108.7C11B—C10B—H33109.5
C9A—C10A—H7108.7H32—C10B—H33108.0
C11A—C10A—H8108.7C12B—C11B—C10B115.2 (3)
C9A—C10A—H8108.7C12B—C11B—H34108.5
H7—C10A—H8107.6C10B—C11B—H34108.5
C12A—C11A—C10A113.7 (3)C12B—C11B—H35108.5
C12A—C11A—H9108.8C10B—C11B—H35108.5
C10A—C11A—H9108.8H34—C11B—H35107.5
C12A—C11A—H10108.8C11B—C12B—H36109.5
C10A—C11A—H10108.8C11B—C12B—H37109.5
H9—C11A—H10107.7H36—C12B—H37109.5
C11A—C12A—H11109.5C11B—C12B—H38109.5
C11A—C12A—H12109.5H36—C12B—H38109.5
H11—C12A—H12109.5H37—C12B—H38109.5
C11A—C12A—H13109.5C14B—C13B—C16B107.7 (2)
H11—C12A—H13109.5C14B—C13B—C15B110.2 (2)
H12—C12A—H13109.5C16B—C13B—C15B107.1 (2)
C14A—C13A—C16A107.1 (3)C14B—C13B—C3B110.85 (19)
C14A—C13A—C15A110.2 (2)C16B—C13B—C3B111.6 (2)
C16A—C13A—C15A107.5 (3)C15B—C13B—C3B109.31 (19)
C14A—C13A—C3A109.8 (2)C13B—C14B—H39109.5
C16A—C13A—C3A111.2 (2)C13B—C14B—H40109.5
C15A—C13A—C3A110.9 (2)H39—C14B—H40109.5
C13A—C14A—H14109.5C13B—C14B—H41109.5
C13A—C14A—H15109.5H39—C14B—H41109.5
H14—C14A—H15109.5H40—C14B—H41109.5
C13A—C14A—H16109.5C13B—C15B—H42109.5
H14—C14A—H16109.5C13B—C15B—H43109.5
H15—C14A—H16109.5H42—C15B—H43109.5
C13A—C15A—H17109.5C13B—C15B—H44109.5
C13A—C15A—H18109.5H42—C15B—H44109.5
H17—C15A—H18109.5H43—C15B—H44109.5
C13A—C15A—H19109.5C13B—C16B—H45109.5
H17—C15A—H19109.5C13B—C16B—H46109.5
H18—C15A—H19109.5H45—C16B—H46109.5
C13A—C16A—H20109.5C13B—C16B—H47109.5
C13A—C16A—H21109.5H45—C16B—H47109.5
H20—C16A—H21109.5H46—C16B—H47109.5
C13A—C16A—H22109.5C5B—C17B—H48109.5
H20—C16A—H22109.5C5B—C17B—H49109.5
H21—C16A—H22109.5H48—C17B—H49109.5
C5A—C17A—H23109.5C5B—C17B—H50109.5
C5A—C17A—H24109.5H48—C17B—H50109.5
H23—C17A—H24109.5H49—C17B—H50109.5

Experimental details

Crystal data
Chemical formula[Zn(C17H26NOS2)2]
Mr714.39
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)8.936 (3), 10.762 (2), 19.740 (3)
α, β, γ (°)80.63 (1), 88.39 (2), 84.11 (2)
V3)1863.0 (8)
Z2
Radiation typeMo Kα
µ (mm1)0.91
Crystal size (mm)0.35 × 0.28 × 0.25
Data collection
DiffractometerEnraf-Nonius CAD-4
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.683, 0.796
No. of measured, independent and
observed [I > 2σ(I)] reflections
6539, 6517, 5755
Rint0.008
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.101, 1.07
No. of reflections6517
No. of parameters397
No. of restraints118
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.37, 0.44

Computer programs: CAD-4 (Enraf-Nonius, 1977), CAD-4, PROCESS in MolEN (Fair, 1990), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL (Sheldrick, 1999), SHELXL97.

 

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