Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803007372/bt6255sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803007372/bt6255Isup2.hkl |
CCDC reference: 214559
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.
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.
Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids (SHELXTL; Sheldrick, 1999). H atoms have been omitted for clarity. |
[Zn(C17H26NOS2)2] | Z = 2 |
Mr = 714.39 | F(000) = 760 |
Triclinic, P1 | Dx = 1.273 Mg m−3 |
a = 8.936 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.762 (2) Å | Cell parameters from 25 reflections |
c = 19.740 (3) Å | θ = 12–20° |
α = 80.63 (1)° | µ = 0.91 mm−1 |
β = 88.39 (2)° | T = 293 K |
γ = 84.11 (2)° | Prismatic, colourless |
V = 1863.0 (8) Å3 | 0.35 × 0.28 × 0.25 mm |
Enraf-Nonius CAD-4 diffractometer | 5755 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.008 |
Graphite monochromator | θmax = 25.0°, θmin = 1.9° |
2θ–ω scans | h = 0→10 |
Absorption correction: ψ scan (North et al., 1968) | k = −12→12 |
Tmin = 0.683, Tmax = 0.796 | l = −23→23 |
6539 measured reflections | 3 standard reflections every 120 min |
6517 independent reflections | intensity decay: 1.5% |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.038 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.101 | Calculated w = 1/[σ2(Fo2) + (0.0517P)2 + 0.9487P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max = 0.001 |
6517 reflections | Δρmax = 0.37 e Å−3 |
397 parameters | Δρmin = −0.44 e Å−3 |
118 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0021 (5) |
[Zn(C17H26NOS2)2] | γ = 84.11 (2)° |
Mr = 714.39 | V = 1863.0 (8) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.936 (3) Å | Mo Kα radiation |
b = 10.762 (2) Å | µ = 0.91 mm−1 |
c = 19.740 (3) Å | T = 293 K |
α = 80.63 (1)° | 0.35 × 0.28 × 0.25 mm |
β = 88.39 (2)° |
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 = 0.796 | 3 standard reflections every 120 min |
6539 measured reflections | intensity decay: 1.5% |
6517 independent reflections |
R[F2 > 2σ(F2)] = 0.038 | 118 restraints |
wR(F2) = 0.101 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | Δρmax = 0.37 e Å−3 |
6517 reflections | Δρmin = −0.44 e Å−3 |
397 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Zn | 0.18643 (3) | 0.78001 (3) | 0.047980 (14) | 0.05466 (12) | |
S1A | 0.13501 (7) | 0.78407 (6) | 0.16598 (3) | 0.05060 (16) | |
S2A | 0.02705 (9) | 0.62218 (7) | 0.07508 (3) | 0.0619 (2) | |
O1A | 0.24499 (19) | 0.52297 (19) | 0.28275 (9) | 0.0594 (5) | |
N1A | −0.0495 (2) | 0.60536 (17) | 0.20710 (9) | 0.0433 (4) | |
C1A | −0.0039 (2) | 0.5404 (2) | 0.33196 (11) | 0.0411 (5) | |
C2A | 0.1429 (2) | 0.4836 (2) | 0.33291 (10) | 0.0427 (5) | |
C3A | 0.1924 (3) | 0.3836 (2) | 0.38413 (11) | 0.0443 (5) | |
C4A | 0.0885 (3) | 0.3488 (2) | 0.43597 (11) | 0.0466 (5) | |
H1 | 0.1191 | 0.2836 | 0.4713 | 0.056* | |
C5A | −0.0566 (3) | 0.4051 (2) | 0.43806 (11) | 0.0443 (5) | |
C6A | −0.1021 (3) | 0.5002 (2) | 0.38519 (11) | 0.0438 (5) | |
H2 | −0.2003 | 0.5383 | 0.3850 | 0.053* | |
C7A | −0.0598 (3) | 0.6442 (2) | 0.27526 (11) | 0.0460 (5) | |
H3 | −0.1639 | 0.6720 | 0.2848 | 0.055* | |
H4 | −0.0016 | 0.7157 | 0.2748 | 0.055* | |
C8A | 0.0277 (3) | 0.6636 (2) | 0.15531 (11) | 0.0425 (5) | |
C9A | −0.1378 (3) | 0.5005 (2) | 0.19823 (13) | 0.0501 (6) | |
H5 | −0.1457 | 0.4454 | 0.2420 | 0.060* | |
H6 | −0.0851 | 0.4512 | 0.1663 | 0.060* | |
C10A | −0.2942 (3) | 0.5469 (3) | 0.17167 (17) | 0.0655 (7) | |
H7 | −0.3489 | 0.5907 | 0.2054 | 0.079* | |
H8 | −0.2859 | 0.6076 | 0.1300 | 0.079* | |
C11A | −0.3825 (4) | 0.4446 (3) | 0.1568 (2) | 0.0844 (10) | |
H9 | −0.3244 | 0.3966 | 0.1258 | 0.101* | |
H10 | −0.3978 | 0.3875 | 0.1992 | 0.101* | |
C12A | −0.5314 (4) | 0.4917 (3) | 0.1257 (2) | 0.1028 (13) | |
H11 | −0.5817 | 0.4214 | 0.1169 | 0.123* | |
H12 | −0.5174 | 0.5476 | 0.0834 | 0.123* | |
H13 | −0.5913 | 0.5367 | 0.1568 | 0.123* | |
C13A | 0.3514 (3) | 0.3152 (3) | 0.38312 (13) | 0.0558 (6) | |
C14A | 0.3742 (3) | 0.2542 (3) | 0.31875 (16) | 0.0689 (7) | |
H14 | 0.3001 | 0.1960 | 0.3178 | 0.083* | |
H15 | 0.4729 | 0.2095 | 0.3190 | 0.083* | |
H16 | 0.3641 | 0.3185 | 0.2789 | 0.083* | |
C15A | 0.4705 (3) | 0.4069 (4) | 0.38605 (19) | 0.0797 (9) | |
H17 | 0.4582 | 0.4746 | 0.3478 | 0.096* | |
H18 | 0.5690 | 0.3626 | 0.3840 | 0.096* | |
H19 | 0.4589 | 0.4409 | 0.4281 | 0.096* | |
C16A | 0.3757 (4) | 0.2091 (4) | 0.44475 (18) | 0.0927 (11) | |
H20 | 0.3032 | 0.1494 | 0.4440 | 0.111* | |
H21 | 0.3639 | 0.2444 | 0.4865 | 0.111* | |
H22 | 0.4753 | 0.1670 | 0.4424 | 0.111* | |
C17A | −0.1615 (3) | 0.3630 (3) | 0.49651 (12) | 0.0571 (6) | |
H23 | −0.2578 | 0.4113 | 0.4894 | 0.069* | |
H24 | −0.1205 | 0.3760 | 0.5389 | 0.069* | |
H25 | −0.1731 | 0.2747 | 0.4985 | 0.069* | |
S1B | 0.42852 (7) | 0.78399 (6) | 0.00006 (3) | 0.05168 (17) | |
S2B | 0.15922 (6) | 0.96083 (6) | −0.03641 (3) | 0.05032 (16) | |
O1B | 0.14910 (19) | 0.97115 (17) | −0.20215 (8) | 0.0516 (4) | |
N1B | 0.42762 (19) | 0.98616 (16) | −0.09759 (9) | 0.0384 (4) | |
C1B | 0.3598 (2) | 1.0957 (2) | −0.21509 (11) | 0.0396 (5) | |
C2B | 0.2536 (2) | 1.03269 (19) | −0.24255 (11) | 0.0388 (5) | |
C3B | 0.2507 (2) | 1.0278 (2) | −0.31290 (11) | 0.0396 (5) | |
C4B | 0.3596 (3) | 1.0871 (2) | −0.35363 (11) | 0.0473 (5) | |
H26 | 0.3608 | 1.0839 | −0.4004 | 0.057* | |
C5B | 0.4683 (3) | 1.1519 (2) | −0.32792 (12) | 0.0501 (6) | |
C6B | 0.4653 (3) | 1.1555 (2) | −0.25899 (12) | 0.0461 (5) | |
H27 | 0.5354 | 1.1988 | −0.2409 | 0.055* | |
C7B | 0.3633 (3) | 1.1038 (2) | −0.13974 (11) | 0.0423 (5) | |
H28 | 0.4219 | 1.1720 | −0.1334 | 0.051* | |
H29 | 0.2615 | 1.1244 | −0.1238 | 0.051* | |
C8B | 0.3484 (2) | 0.9183 (2) | −0.05065 (10) | 0.0385 (5) | |
C9B | 0.5908 (2) | 0.9535 (2) | −0.10700 (12) | 0.0454 (5) | |
H30 | 0.6350 | 0.9210 | −0.0625 | 0.055* | |
H31 | 0.6366 | 1.0299 | −0.1256 | 0.055* | |
C10B | 0.6276 (3) | 0.8570 (3) | −0.15376 (13) | 0.0569 (6) | |
H32 | 0.5891 | 0.8907 | −0.1992 | 0.068* | |
H33 | 0.5790 | 0.7814 | −0.1365 | 0.068* | |
C11B | 0.7977 (3) | 0.8228 (4) | −0.15838 (17) | 0.0805 (9) | |
H34 | 0.8180 | 0.7720 | −0.1945 | 0.097* | |
H35 | 0.8454 | 0.9003 | −0.1717 | 0.097* | |
C12B | 0.8670 (4) | 0.7542 (4) | −0.0956 (2) | 0.0976 (12) | |
H36 | 0.9730 | 0.7363 | −0.1033 | 0.117* | |
H37 | 0.8224 | 0.6763 | −0.0823 | 0.117* | |
H38 | 0.8512 | 0.8049 | −0.0597 | 0.117* | |
C13B | 0.1301 (3) | 0.9610 (2) | −0.34360 (12) | 0.0470 (5) | |
C14B | 0.1359 (3) | 0.8221 (2) | −0.31077 (15) | 0.0613 (7) | |
H39 | 0.0601 | 0.7825 | −0.3305 | 0.074* | |
H40 | 0.1181 | 0.8163 | −0.2622 | 0.074* | |
H41 | 0.2332 | 0.7801 | −0.3189 | 0.074* | |
C15B | −0.0251 (3) | 1.0287 (3) | −0.33246 (15) | 0.0625 (7) | |
H42 | −0.0273 | 1.1161 | −0.3530 | 0.075* | |
H43 | −0.0458 | 1.0229 | −0.2841 | 0.075* | |
H44 | −0.0999 | 0.9896 | −0.3533 | 0.075* | |
C16B | 0.1525 (4) | 0.9658 (3) | −0.42087 (14) | 0.0697 (8) | |
H45 | 0.1497 | 1.0524 | −0.4429 | 0.084* | |
H46 | 0.0738 | 0.9262 | −0.4386 | 0.084* | |
H47 | 0.2481 | 0.9217 | −0.4298 | 0.084* | |
C17B | 0.5842 (3) | 1.2135 (3) | −0.37498 (15) | 0.0747 (9) | |
H48 | 0.5687 | 1.1999 | −0.4210 | 0.090* | |
H49 | 0.6829 | 1.1771 | −0.3604 | 0.090* | |
H50 | 0.5749 | 1.3027 | −0.3736 | 0.090* | |
H51 | 0.205 (4) | 0.590 (2) | 0.2584 (15) | 0.089 (12)* | |
H52 | 0.150 (4) | 0.981 (3) | −0.1608 (7) | 0.086 (11)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn | 0.0602 (2) | 0.0636 (2) | 0.03891 (17) | −0.02071 (14) | 0.00768 (12) | 0.00313 (13) |
S1A | 0.0630 (4) | 0.0513 (3) | 0.0395 (3) | −0.0252 (3) | 0.0044 (3) | −0.0018 (2) |
S2A | 0.0820 (5) | 0.0693 (4) | 0.0395 (3) | −0.0353 (4) | 0.0035 (3) | −0.0072 (3) |
O1A | 0.0434 (9) | 0.0785 (13) | 0.0482 (10) | −0.0085 (9) | 0.0107 (8) | 0.0131 (9) |
N1A | 0.0502 (11) | 0.0407 (10) | 0.0374 (9) | −0.0128 (8) | −0.0016 (8) | 0.0038 (8) |
C1A | 0.0438 (12) | 0.0464 (12) | 0.0332 (10) | −0.0121 (9) | 0.0030 (9) | −0.0023 (9) |
C2A | 0.0419 (12) | 0.0562 (13) | 0.0298 (10) | −0.0150 (10) | 0.0049 (9) | −0.0008 (9) |
C3A | 0.0439 (12) | 0.0558 (13) | 0.0335 (11) | −0.0099 (10) | −0.0031 (9) | −0.0040 (9) |
C4A | 0.0536 (13) | 0.0541 (13) | 0.0312 (11) | −0.0155 (11) | −0.0040 (9) | 0.0029 (9) |
C5A | 0.0506 (13) | 0.0546 (13) | 0.0303 (10) | −0.0200 (10) | 0.0040 (9) | −0.0056 (9) |
C6A | 0.0410 (12) | 0.0534 (13) | 0.0377 (11) | −0.0118 (10) | 0.0043 (9) | −0.0058 (10) |
C7A | 0.0502 (13) | 0.0449 (12) | 0.0409 (12) | −0.0072 (10) | 0.0067 (10) | −0.0005 (9) |
C8A | 0.0474 (12) | 0.0393 (11) | 0.0387 (11) | −0.0097 (9) | −0.0031 (9) | 0.0038 (9) |
C9A | 0.0594 (14) | 0.0417 (12) | 0.0479 (13) | −0.0184 (10) | −0.0007 (11) | 0.0053 (10) |
C10A | 0.0619 (16) | 0.0521 (15) | 0.082 (2) | −0.0156 (12) | −0.0024 (14) | −0.0033 (14) |
C11A | 0.073 (2) | 0.0599 (17) | 0.118 (3) | −0.0246 (15) | −0.0251 (19) | 0.0067 (17) |
C12A | 0.085 (2) | 0.067 (2) | 0.152 (4) | −0.0225 (18) | −0.036 (2) | 0.010 (2) |
C13A | 0.0467 (13) | 0.0702 (16) | 0.0470 (13) | −0.0011 (12) | −0.0054 (11) | −0.0012 (12) |
C14A | 0.0583 (16) | 0.0737 (18) | 0.0740 (18) | 0.0001 (14) | 0.0057 (14) | −0.0149 (15) |
C15A | 0.0467 (15) | 0.103 (2) | 0.093 (2) | −0.0083 (15) | −0.0136 (15) | −0.0243 (19) |
C16A | 0.075 (2) | 0.110 (3) | 0.074 (2) | 0.0233 (19) | −0.0068 (17) | 0.0229 (19) |
C17A | 0.0608 (15) | 0.0730 (17) | 0.0384 (12) | −0.0259 (13) | 0.0104 (11) | −0.0011 (11) |
S1B | 0.0528 (3) | 0.0509 (3) | 0.0440 (3) | 0.0021 (3) | 0.0049 (3) | 0.0087 (3) |
S2B | 0.0386 (3) | 0.0663 (4) | 0.0402 (3) | −0.0002 (3) | 0.0055 (2) | 0.0048 (3) |
O1B | 0.0513 (10) | 0.0674 (11) | 0.0390 (9) | −0.0290 (8) | 0.0077 (7) | −0.0036 (8) |
N1B | 0.0371 (9) | 0.0419 (9) | 0.0344 (9) | −0.0070 (7) | −0.0002 (7) | 0.0004 (7) |
C1B | 0.0411 (11) | 0.0373 (11) | 0.0377 (11) | −0.0056 (9) | −0.0027 (9) | 0.0038 (9) |
C2B | 0.0373 (11) | 0.0374 (11) | 0.0383 (11) | −0.0055 (8) | 0.0018 (9) | 0.0042 (9) |
C3B | 0.0415 (11) | 0.0377 (11) | 0.0373 (11) | −0.0051 (9) | −0.0021 (9) | 0.0020 (9) |
C4B | 0.0515 (13) | 0.0536 (13) | 0.0331 (11) | −0.0084 (10) | 0.0016 (9) | 0.0053 (10) |
C5B | 0.0464 (13) | 0.0562 (14) | 0.0434 (12) | −0.0146 (11) | 0.0023 (10) | 0.0101 (10) |
C6B | 0.0433 (12) | 0.0463 (12) | 0.0467 (12) | −0.0157 (10) | −0.0050 (10) | 0.0068 (10) |
C7B | 0.0479 (12) | 0.0383 (11) | 0.0395 (11) | −0.0093 (9) | −0.0024 (9) | 0.0008 (9) |
C8B | 0.0415 (11) | 0.0441 (11) | 0.0293 (10) | −0.0044 (9) | 0.0001 (8) | −0.0036 (8) |
C9B | 0.0418 (12) | 0.0504 (13) | 0.0431 (12) | −0.0127 (10) | 0.0007 (9) | 0.0002 (10) |
C10B | 0.0537 (14) | 0.0690 (16) | 0.0484 (14) | −0.0018 (12) | −0.0017 (11) | −0.0130 (12) |
C11B | 0.0616 (18) | 0.100 (2) | 0.079 (2) | 0.0047 (17) | 0.0140 (15) | −0.0205 (18) |
C12B | 0.072 (2) | 0.102 (3) | 0.122 (3) | 0.0200 (19) | −0.035 (2) | −0.039 (2) |
C13B | 0.0503 (13) | 0.0492 (13) | 0.0419 (12) | −0.0112 (10) | −0.0044 (10) | −0.0045 (10) |
C14B | 0.0704 (17) | 0.0487 (14) | 0.0672 (17) | −0.0160 (12) | −0.0054 (13) | −0.0096 (12) |
C15B | 0.0488 (14) | 0.0686 (17) | 0.0708 (17) | −0.0101 (12) | −0.0126 (13) | −0.0091 (14) |
C16B | 0.081 (2) | 0.087 (2) | 0.0466 (14) | −0.0271 (16) | −0.0089 (13) | −0.0134 (14) |
C17B | 0.0660 (18) | 0.097 (2) | 0.0587 (17) | −0.0364 (16) | 0.0106 (14) | 0.0109 (15) |
Zn—S2A | 2.3147 (9) | C17A—H24 | 0.9600 |
Zn—S1B | 2.3382 (10) | C17A—H25 | 0.9600 |
Zn—S2B | 2.3433 (8) | S1B—C8B | 1.720 (2) |
Zn—S1A | 2.3680 (7) | S2B—C8B | 1.733 (2) |
S1A—C8A | 1.732 (2) | O1B—C2B | 1.364 (3) |
S2A—C8A | 1.714 (2) | O1B—H52 | 0.840 (10) |
O1A—C2A | 1.373 (3) | N1B—C8B | 1.320 (3) |
O1A—H51 | 0.846 (10) | N1B—C7B | 1.469 (3) |
N1A—C8A | 1.324 (3) | N1B—C9B | 1.479 (3) |
N1A—C7A | 1.471 (3) | C1B—C2B | 1.391 (3) |
N1A—C9A | 1.477 (3) | C1B—C6B | 1.396 (3) |
C1A—C2A | 1.389 (3) | C1B—C7B | 1.505 (3) |
C1A—C6A | 1.393 (3) | C2B—C3B | 1.399 (3) |
C1A—C7A | 1.504 (3) | C3B—C4B | 1.385 (3) |
C2A—C3A | 1.396 (3) | C3B—C13B | 1.543 (3) |
C3A—C4A | 1.394 (3) | C4B—C5B | 1.403 (3) |
C3A—C13A | 1.532 (3) | C4B—H26 | 0.9300 |
C4A—C5A | 1.376 (3) | C5B—C6B | 1.367 (3) |
C4A—H1 | 0.9300 | C5B—C17B | 1.504 (3) |
C5A—C6A | 1.375 (3) | C6B—H27 | 0.9300 |
C5A—C17A | 1.507 (3) | C7B—H28 | 0.9700 |
C6A—H2 | 0.9300 | C7B—H29 | 0.9700 |
C7A—H3 | 0.9700 | C9B—C10B | 1.504 (3) |
C7A—H4 | 0.9700 | C9B—H30 | 0.9700 |
C9A—C10A | 1.514 (4) | C9B—H31 | 0.9700 |
C9A—H5 | 0.9700 | C10B—C11B | 1.530 (4) |
C9A—H6 | 0.9700 | C10B—H32 | 0.9700 |
C10A—C11A | 1.489 (4) | C10B—H33 | 0.9700 |
C10A—H7 | 0.9700 | C11B—C12B | 1.455 (5) |
C10A—H8 | 0.9700 | C11B—H34 | 0.9700 |
C11A—C12A | 1.486 (5) | C11B—H35 | 0.9700 |
C11A—H9 | 0.9700 | C12B—H36 | 0.9600 |
C11A—H10 | 0.9700 | C12B—H37 | 0.9600 |
C12A—H11 | 0.9600 | C12B—H38 | 0.9600 |
C12A—H12 | 0.9600 | C13B—C14B | 1.526 (3) |
C12A—H13 | 0.9600 | C13B—C16B | 1.526 (3) |
C13A—C14A | 1.522 (4) | C13B—C15B | 1.527 (4) |
C13A—C16A | 1.530 (4) | C14B—H39 | 0.9600 |
C13A—C15A | 1.532 (4) | C14B—H40 | 0.9600 |
C14A—H14 | 0.9600 | C14B—H41 | 0.9600 |
C14A—H15 | 0.9600 | C15B—H42 | 0.9600 |
C14A—H16 | 0.9600 | C15B—H43 | 0.9600 |
C15A—H17 | 0.9600 | C15B—H44 | 0.9600 |
C15A—H18 | 0.9600 | C16B—H45 | 0.9600 |
C15A—H19 | 0.9600 | C16B—H46 | 0.9600 |
C16A—H20 | 0.9600 | C16B—H47 | 0.9600 |
C16A—H21 | 0.9600 | C17B—H48 | 0.9600 |
C16A—H22 | 0.9600 | C17B—H49 | 0.9600 |
C17A—H23 | 0.9600 | C17B—H50 | 0.9600 |
S2A—Zn—S1B | 133.24 (3) | C5A—C17A—H25 | 109.5 |
S2A—Zn—S2B | 128.80 (3) | H23—C17A—H25 | 109.5 |
S1B—Zn—S2B | 77.80 (3) | H24—C17A—H25 | 109.5 |
S2A—Zn—S1A | 77.78 (3) | C8B—S1B—Zn | 82.94 (8) |
S1B—Zn—S1A | 123.11 (3) | C8B—S2B—Zn | 82.54 (8) |
S2B—Zn—S1A | 123.28 (3) | C2B—O1B—H52 | 114 (2) |
C8A—S1A—Zn | 81.55 (8) | C8B—N1B—C7B | 122.63 (18) |
C8A—S2A—Zn | 83.53 (8) | C8B—N1B—C9B | 121.54 (18) |
C2A—O1A—H51 | 108 (2) | C7B—N1B—C9B | 115.65 (17) |
C8A—N1A—C7A | 122.86 (19) | C2B—C1B—C6B | 119.0 (2) |
C8A—N1A—C9A | 121.22 (19) | C2B—C1B—C7B | 122.22 (19) |
C7A—N1A—C9A | 115.84 (18) | C6B—C1B—C7B | 118.8 (2) |
C2A—C1A—C6A | 119.0 (2) | O1B—C2B—C1B | 121.68 (19) |
C2A—C1A—C7A | 121.94 (19) | O1B—C2B—C3B | 116.86 (19) |
C6A—C1A—C7A | 119.1 (2) | C1B—C2B—C3B | 121.45 (19) |
O1A—C2A—C1A | 121.0 (2) | C4B—C3B—C2B | 116.8 (2) |
O1A—C2A—C3A | 117.3 (2) | C4B—C3B—C13B | 121.7 (2) |
C1A—C2A—C3A | 121.70 (19) | C2B—C3B—C13B | 121.43 (19) |
C4A—C3A—C2A | 116.1 (2) | C3B—C4B—C5B | 123.4 (2) |
C4A—C3A—C13A | 121.9 (2) | C3B—C4B—H26 | 118.3 |
C2A—C3A—C13A | 122.0 (2) | C5B—C4B—H26 | 118.3 |
C5A—C4A—C3A | 124.0 (2) | C6B—C5B—C4B | 117.6 (2) |
C5A—C4A—H1 | 118.0 | C6B—C5B—C17B | 121.8 (2) |
C3A—C4A—H1 | 118.0 | C4B—C5B—C17B | 120.6 (2) |
C6A—C5A—C4A | 117.8 (2) | C5B—C6B—C1B | 121.7 (2) |
C6A—C5A—C17A | 121.5 (2) | C5B—C6B—H27 | 119.1 |
C4A—C5A—C17A | 120.7 (2) | C1B—C6B—H27 | 119.1 |
C5A—C6A—C1A | 121.3 (2) | N1B—C7B—C1B | 113.36 (18) |
C5A—C6A—H2 | 119.4 | N1B—C7B—H28 | 108.9 |
C1A—C6A—H2 | 119.4 | C1B—C7B—H28 | 108.9 |
N1A—C7A—C1A | 113.22 (18) | N1B—C7B—H29 | 108.9 |
N1A—C7A—H3 | 108.9 | C1B—C7B—H29 | 108.9 |
C1A—C7A—H3 | 108.9 | H28—C7B—H29 | 107.7 |
N1A—C7A—H4 | 108.9 | N1B—C8B—S1B | 121.57 (16) |
C1A—C7A—H4 | 108.9 | N1B—C8B—S2B | 121.71 (16) |
H3—C7A—H4 | 107.7 | S1B—C8B—S2B | 116.73 (12) |
N1A—C8A—S2A | 121.48 (17) | N1B—C9B—C10B | 113.69 (19) |
N1A—C8A—S1A | 121.38 (17) | N1B—C9B—H30 | 108.8 |
S2A—C8A—S1A | 117.14 (13) | C10B—C9B—H30 | 108.8 |
N1A—C9A—C10A | 112.4 (2) | N1B—C9B—H31 | 108.8 |
N1A—C9A—H5 | 109.1 | C10B—C9B—H31 | 108.8 |
C10A—C9A—H5 | 109.1 | H30—C9B—H31 | 107.7 |
N1A—C9A—H6 | 109.1 | C9B—C10B—C11B | 110.9 (2) |
C10A—C9A—H6 | 109.1 | C9B—C10B—H32 | 109.5 |
H5—C9A—H6 | 107.8 | C11B—C10B—H32 | 109.5 |
C11A—C10A—C9A | 114.0 (2) | C9B—C10B—H33 | 109.5 |
C11A—C10A—H7 | 108.7 | C11B—C10B—H33 | 109.5 |
C9A—C10A—H7 | 108.7 | H32—C10B—H33 | 108.0 |
C11A—C10A—H8 | 108.7 | C12B—C11B—C10B | 115.2 (3) |
C9A—C10A—H8 | 108.7 | C12B—C11B—H34 | 108.5 |
H7—C10A—H8 | 107.6 | C10B—C11B—H34 | 108.5 |
C12A—C11A—C10A | 113.7 (3) | C12B—C11B—H35 | 108.5 |
C12A—C11A—H9 | 108.8 | C10B—C11B—H35 | 108.5 |
C10A—C11A—H9 | 108.8 | H34—C11B—H35 | 107.5 |
C12A—C11A—H10 | 108.8 | C11B—C12B—H36 | 109.5 |
C10A—C11A—H10 | 108.8 | C11B—C12B—H37 | 109.5 |
H9—C11A—H10 | 107.7 | H36—C12B—H37 | 109.5 |
C11A—C12A—H11 | 109.5 | C11B—C12B—H38 | 109.5 |
C11A—C12A—H12 | 109.5 | H36—C12B—H38 | 109.5 |
H11—C12A—H12 | 109.5 | H37—C12B—H38 | 109.5 |
C11A—C12A—H13 | 109.5 | C14B—C13B—C16B | 107.7 (2) |
H11—C12A—H13 | 109.5 | C14B—C13B—C15B | 110.2 (2) |
H12—C12A—H13 | 109.5 | C16B—C13B—C15B | 107.1 (2) |
C14A—C13A—C16A | 107.1 (3) | C14B—C13B—C3B | 110.85 (19) |
C14A—C13A—C15A | 110.2 (2) | C16B—C13B—C3B | 111.6 (2) |
C16A—C13A—C15A | 107.5 (3) | C15B—C13B—C3B | 109.31 (19) |
C14A—C13A—C3A | 109.8 (2) | C13B—C14B—H39 | 109.5 |
C16A—C13A—C3A | 111.2 (2) | C13B—C14B—H40 | 109.5 |
C15A—C13A—C3A | 110.9 (2) | H39—C14B—H40 | 109.5 |
C13A—C14A—H14 | 109.5 | C13B—C14B—H41 | 109.5 |
C13A—C14A—H15 | 109.5 | H39—C14B—H41 | 109.5 |
H14—C14A—H15 | 109.5 | H40—C14B—H41 | 109.5 |
C13A—C14A—H16 | 109.5 | C13B—C15B—H42 | 109.5 |
H14—C14A—H16 | 109.5 | C13B—C15B—H43 | 109.5 |
H15—C14A—H16 | 109.5 | H42—C15B—H43 | 109.5 |
C13A—C15A—H17 | 109.5 | C13B—C15B—H44 | 109.5 |
C13A—C15A—H18 | 109.5 | H42—C15B—H44 | 109.5 |
H17—C15A—H18 | 109.5 | H43—C15B—H44 | 109.5 |
C13A—C15A—H19 | 109.5 | C13B—C16B—H45 | 109.5 |
H17—C15A—H19 | 109.5 | C13B—C16B—H46 | 109.5 |
H18—C15A—H19 | 109.5 | H45—C16B—H46 | 109.5 |
C13A—C16A—H20 | 109.5 | C13B—C16B—H47 | 109.5 |
C13A—C16A—H21 | 109.5 | H45—C16B—H47 | 109.5 |
H20—C16A—H21 | 109.5 | H46—C16B—H47 | 109.5 |
C13A—C16A—H22 | 109.5 | C5B—C17B—H48 | 109.5 |
H20—C16A—H22 | 109.5 | C5B—C17B—H49 | 109.5 |
H21—C16A—H22 | 109.5 | H48—C17B—H49 | 109.5 |
C5A—C17A—H23 | 109.5 | C5B—C17B—H50 | 109.5 |
C5A—C17A—H24 | 109.5 | H48—C17B—H50 | 109.5 |
H23—C17A—H24 | 109.5 | H49—C17B—H50 | 109.5 |
Experimental details
Crystal data | |
Chemical formula | [Zn(C17H26NOS2)2] |
Mr | 714.39 |
Crystal system, space group | Triclinic, 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) |
V (Å3) | 1863.0 (8) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.91 |
Crystal size (mm) | 0.35 × 0.28 × 0.25 |
Data collection | |
Diffractometer | Enraf-Nonius CAD-4 diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.683, 0.796 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6539, 6517, 5755 |
Rint | 0.008 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.101, 1.07 |
No. of reflections | 6517 |
No. of parameters | 397 |
No. of restraints | 118 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 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.
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.