metal-organic compounds
In the title compound, (C16H36N2)2[Pd(C4N2S2)2], the PdII ion, located on an inversion centre, is coordinated by the four S atoms of the two ligands, giving a coordination geometry very close to ideal square-planar.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807015541/bh2096sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807015541/bh2096Isup2.hkl |
CCDC reference: 646727
Computing details top
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1994); data reduction: XPREP (Siemens, 1994); program(s) used to solve structure: SHELXTL (Siemens, 1994); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Crystal data top
(C16H36N2)2[Pd(C4N2S2)2] | Z = 1 |
Mr = 871.74 | F(000) = 464 |
Triclinic, P1 | Dx = 1.215 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.7986 (11) Å | Cell parameters from 2635 reflections |
b = 10.8084 (12) Å | θ = 1.7–25.1° |
c = 12.4030 (13) Å | µ = 0.60 mm−1 |
α = 85.631 (2)° | T = 293 K |
β = 87.964 (2)° | Prism, green |
γ = 65.476 (2)° | 0.56 × 0.26 × 0.22 mm |
V = 1191.6 (2) Å3 |
Data collection top
Siemens SMART CCD diffractometer | 4181 independent reflections |
Radiation source: fine-focus sealed tube | 3178 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
φ and ω scans | θmax = 25.1°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −7→11 |
Tmin = 0.713, Tmax = 0.877 | k = −12→12 |
6213 measured reflections | l = −14→14 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.065 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.148 | H-atom parameters constrained |
S = 1.15 | w = 1/[σ2(Fo2) + (0.0377P)2 + 2.3236P] where P = (Fo2 + 2Fc2)/3 |
4181 reflections | (Δ/σ)max < 0.001 |
232 parameters | Δρmax = 0.47 e Å−3 |
0 restraints | Δρmin = −0.64 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Pd1 | 1.5000 | −1.0000 | 1.5000 | 0.0542 (2) | |
S1 | 1.38629 (18) | −0.77325 (16) | 1.53277 (14) | 0.0704 (5) | |
S2 | 1.34516 (17) | −0.95959 (15) | 1.35469 (13) | 0.0628 (4) | |
N1 | 1.3909 (8) | −0.5371 (7) | 1.7292 (7) | 0.132 (3) | |
N2 | 1.2810 (7) | −1.1325 (7) | 1.1311 (5) | 0.0892 (18) | |
N11 | 1.2083 (5) | −1.0866 (4) | 0.7782 (3) | 0.0533 (11) | |
C1 | 1.3412 (7) | −1.1296 (6) | 1.2076 (5) | 0.0664 (16) | |
C2 | 1.4106 (6) | −1.1202 (6) | 1.3043 (5) | 0.0564 (14) | |
C3 | 1.4780 (6) | −0.7688 (6) | 1.6478 (5) | 0.0584 (14) | |
C4 | 1.4313 (7) | −0.6401 (8) | 1.6925 (6) | 0.083 (2) | |
C11 | 1.2052 (7) | −1.0010 (6) | 0.8701 (4) | 0.0610 (15) | |
H11A | 1.2280 | −1.0589 | 0.9367 | 0.073* | |
H11B | 1.1041 | −0.9313 | 0.8768 | 0.073* | |
C12 | 1.3124 (8) | −0.9320 (7) | 0.8594 (6) | 0.0809 (19) | |
H12A | 1.3012 | −0.8845 | 0.7885 | 0.097* | |
H12B | 1.4147 | −1.0006 | 0.8658 | 0.097* | |
C13 | 1.2821 (9) | −0.8301 (7) | 0.9468 (6) | 0.091 (2) | |
H13A | 1.2761 | −0.8742 | 1.0167 | 0.109* | |
H13B | 1.3658 | −0.8044 | 0.9487 | 0.109* | |
C14 | 1.1425 (11) | −0.7059 (9) | 0.9283 (8) | 0.127 (3) | |
H14A | 1.1284 | −0.6467 | 0.9855 | 0.191* | |
H14B | 1.0590 | −0.7304 | 0.9269 | 0.191* | |
H14C | 1.1491 | −0.6597 | 0.8604 | 0.191* | |
C21 | 1.1580 (6) | −0.9990 (6) | 0.6738 (4) | 0.0590 (14) | |
H21A | 1.1622 | −1.0575 | 0.6170 | 0.071* | |
H21B | 1.2294 | −0.9598 | 0.6550 | 0.071* | |
C22 | 1.0018 (7) | −0.8838 (7) | 0.6745 (6) | 0.084 (2) | |
H22A | 0.9283 | −0.9224 | 0.6823 | 0.101* | |
H22B | 0.9922 | −0.8314 | 0.7367 | 0.101* | |
C23 | 0.9692 (8) | −0.7932 (8) | 0.5774 (6) | 0.101 (3) | |
H23A | 0.9815 | −0.8468 | 0.5156 | 0.122* | |
H23B | 1.0429 | −0.7547 | 0.5705 | 0.122* | |
C24 | 0.8150 (8) | −0.6777 (8) | 0.5724 (6) | 0.101 (3) | |
H24A | 0.8046 | −0.6230 | 0.5059 | 0.151* | |
H24B | 0.8017 | −0.6224 | 0.6323 | 0.151* | |
H24C | 0.7406 | −0.7140 | 0.5758 | 0.151* | |
C31 | 1.3672 (6) | −1.1915 (6) | 0.7584 (5) | 0.0572 (14) | |
H31A | 1.3654 | −1.2409 | 0.6968 | 0.069* | |
H31B | 1.4296 | −1.1431 | 0.7387 | 0.069* | |
C32 | 1.4407 (6) | −1.2937 (6) | 0.8512 (5) | 0.0609 (15) | |
H32A | 1.3889 | −1.3528 | 0.8648 | 0.073* | |
H32B | 1.4338 | −1.2464 | 0.9160 | 0.073* | |
C33 | 1.6041 (7) | −1.3785 (7) | 0.8252 (7) | 0.090 (2) | |
H33A | 1.6580 | −1.3207 | 0.8216 | 0.108* | |
H33B | 1.6109 | −1.4138 | 0.7546 | 0.108* | |
C34 | 1.6782 (8) | −1.4969 (8) | 0.9084 (7) | 0.110 (3) | |
H34A | 1.7809 | −1.5479 | 0.8881 | 0.165* | |
H34B | 1.6260 | −1.5552 | 0.9117 | 0.165* | |
H34C | 1.6746 | −1.4625 | 0.9781 | 0.165* | |
C41 | 1.1043 (6) | −1.1553 (6) | 0.8100 (5) | 0.0583 (14) | |
H41A | 1.1433 | −1.2139 | 0.8751 | 0.070* | |
H41B | 1.0071 | −1.0854 | 0.8281 | 0.070* | |
C42 | 1.0813 (6) | −1.2396 (6) | 0.7266 (5) | 0.0635 (15) | |
H42A | 1.1777 | −1.2979 | 0.6970 | 0.076* | |
H42B | 1.0210 | −1.1796 | 0.6678 | 0.076* | |
C43 | 1.0041 (7) | −1.3267 (7) | 0.7752 (6) | 0.0759 (18) | |
H43A | 1.0652 | −1.3870 | 0.8335 | 0.091* | |
H43B | 0.9086 | −1.2681 | 0.8059 | 0.091* | |
C44 | 0.9774 (8) | −1.4111 (7) | 0.6932 (6) | 0.089 (2) | |
H44A | 0.9290 | −1.4647 | 0.7280 | 0.133* | |
H44B | 1.0717 | −1.4704 | 0.6634 | 0.133* | |
H44C | 0.9147 | −1.3518 | 0.6363 | 0.133* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Pd1 | 0.0468 (4) | 0.0486 (4) | 0.0631 (4) | −0.0165 (3) | 0.0000 (3) | 0.0016 (3) |
S1 | 0.0651 (10) | 0.0511 (9) | 0.0857 (12) | −0.0138 (8) | −0.0196 (9) | −0.0021 (8) |
S2 | 0.0562 (9) | 0.0532 (9) | 0.0703 (10) | −0.0140 (7) | −0.0094 (8) | 0.0013 (8) |
N1 | 0.098 (5) | 0.087 (5) | 0.192 (8) | −0.007 (4) | −0.044 (5) | −0.058 (5) |
N2 | 0.096 (4) | 0.105 (5) | 0.061 (4) | −0.035 (4) | −0.010 (3) | −0.003 (3) |
N11 | 0.048 (2) | 0.057 (3) | 0.052 (3) | −0.020 (2) | 0.004 (2) | −0.002 (2) |
C1 | 0.059 (4) | 0.067 (4) | 0.066 (4) | −0.019 (3) | 0.003 (3) | −0.003 (3) |
C2 | 0.049 (3) | 0.063 (4) | 0.058 (4) | −0.023 (3) | 0.000 (3) | −0.005 (3) |
C3 | 0.050 (3) | 0.055 (3) | 0.071 (4) | −0.021 (3) | −0.001 (3) | −0.007 (3) |
C4 | 0.064 (4) | 0.075 (5) | 0.105 (6) | −0.018 (4) | −0.022 (4) | −0.023 (4) |
C11 | 0.065 (4) | 0.060 (3) | 0.051 (3) | −0.019 (3) | 0.002 (3) | 0.001 (3) |
C12 | 0.078 (4) | 0.087 (5) | 0.085 (5) | −0.040 (4) | 0.008 (4) | −0.018 (4) |
C13 | 0.111 (6) | 0.075 (5) | 0.084 (5) | −0.034 (4) | −0.009 (4) | −0.014 (4) |
C14 | 0.141 (8) | 0.084 (6) | 0.138 (8) | −0.025 (6) | −0.009 (7) | −0.019 (6) |
C21 | 0.065 (4) | 0.063 (4) | 0.049 (3) | −0.029 (3) | −0.005 (3) | 0.011 (3) |
C22 | 0.063 (4) | 0.091 (5) | 0.078 (5) | −0.017 (4) | 0.005 (3) | 0.022 (4) |
C23 | 0.084 (5) | 0.099 (6) | 0.093 (6) | −0.016 (5) | −0.005 (4) | 0.025 (5) |
C24 | 0.081 (5) | 0.092 (5) | 0.103 (6) | −0.016 (4) | −0.013 (4) | 0.034 (5) |
C31 | 0.048 (3) | 0.062 (3) | 0.060 (3) | −0.021 (3) | 0.006 (3) | −0.011 (3) |
C32 | 0.054 (3) | 0.056 (3) | 0.068 (4) | −0.018 (3) | −0.005 (3) | −0.001 (3) |
C33 | 0.056 (4) | 0.079 (5) | 0.125 (6) | −0.019 (4) | −0.005 (4) | 0.001 (4) |
C34 | 0.066 (5) | 0.085 (5) | 0.155 (8) | −0.011 (4) | −0.021 (5) | 0.023 (5) |
C41 | 0.046 (3) | 0.064 (4) | 0.061 (3) | −0.021 (3) | 0.003 (3) | 0.009 (3) |
C42 | 0.057 (3) | 0.066 (4) | 0.070 (4) | −0.029 (3) | −0.004 (3) | 0.008 (3) |
C43 | 0.062 (4) | 0.071 (4) | 0.096 (5) | −0.032 (3) | −0.006 (4) | 0.011 (4) |
C44 | 0.080 (5) | 0.080 (5) | 0.115 (6) | −0.043 (4) | −0.013 (4) | 0.002 (4) |
Geometric parameters (Å, º) top
Pd1—S1 | 2.2947 (16) | C22—H22A | 0.9700 |
Pd1—S1i | 2.2947 (16) | C22—H22B | 0.9700 |
Pd1—S2i | 2.2945 (15) | C23—C24 | 1.508 (9) |
Pd1—S2 | 2.2945 (16) | C23—H23A | 0.9700 |
S1—C3 | 1.727 (6) | C23—H23B | 0.9700 |
S2—C2 | 1.740 (6) | C24—H24A | 0.9600 |
N1—C4 | 1.141 (8) | C24—H24B | 0.9600 |
N2—C1 | 1.144 (8) | C24—H24C | 0.9600 |
N11—C21 | 1.512 (6) | C31—C32 | 1.506 (8) |
N11—C11 | 1.514 (7) | C31—H31A | 0.9700 |
N11—C41 | 1.518 (7) | C31—H31B | 0.9700 |
N11—C31 | 1.524 (6) | C32—C33 | 1.516 (8) |
C1—C2 | 1.431 (9) | C32—H32A | 0.9700 |
C2—C3i | 1.355 (8) | C32—H32B | 0.9700 |
C3—C2i | 1.355 (8) | C33—C34 | 1.521 (10) |
C3—C4 | 1.422 (9) | C33—H33A | 0.9700 |
C11—C12 | 1.517 (8) | C33—H33B | 0.9700 |
C11—H11A | 0.9700 | C34—H34A | 0.9600 |
C11—H11B | 0.9700 | C34—H34B | 0.9600 |
C12—C13 | 1.538 (9) | C34—H34C | 0.9600 |
C12—H12A | 0.9700 | C41—C42 | 1.511 (8) |
C12—H12B | 0.9700 | C41—H41A | 0.9700 |
C13—C14 | 1.476 (10) | C41—H41B | 0.9700 |
C13—H13A | 0.9700 | C42—C43 | 1.515 (8) |
C13—H13B | 0.9700 | C42—H42A | 0.9700 |
C14—H14A | 0.9600 | C42—H42B | 0.9700 |
C14—H14B | 0.9600 | C43—C44 | 1.515 (9) |
C14—H14C | 0.9600 | C43—H43A | 0.9700 |
C21—C22 | 1.521 (8) | C43—H43B | 0.9700 |
C21—H21A | 0.9700 | C44—H44A | 0.9600 |
C21—H21B | 0.9700 | C44—H44B | 0.9600 |
C22—C23 | 1.449 (9) | C44—H44C | 0.9600 |
S2i—Pd1—S2 | 180.000 (1) | C22—C23—H23A | 108.4 |
S2i—Pd1—S1 | 90.10 (6) | C24—C23—H23A | 108.4 |
S2—Pd1—S1 | 89.90 (6) | C22—C23—H23B | 108.4 |
S2i—Pd1—S1i | 89.90 (6) | C24—C23—H23B | 108.4 |
S2—Pd1—S1i | 90.10 (6) | H23A—C23—H23B | 107.4 |
S1—Pd1—S1i | 180.000 (1) | C23—C24—H24A | 109.5 |
C3—S1—Pd1 | 101.8 (2) | C23—C24—H24B | 109.5 |
C2—S2—Pd1 | 101.8 (2) | H24A—C24—H24B | 109.5 |
C21—N11—C11 | 110.9 (4) | C23—C24—H24C | 109.5 |
C21—N11—C41 | 110.9 (4) | H24A—C24—H24C | 109.5 |
C11—N11—C41 | 106.9 (4) | H24B—C24—H24C | 109.5 |
C21—N11—C31 | 106.4 (4) | C32—C31—N11 | 116.3 (4) |
C11—N11—C31 | 110.7 (4) | C32—C31—H31A | 108.2 |
C41—N11—C31 | 111.1 (4) | N11—C31—H31A | 108.2 |
N2—C1—C2 | 177.3 (7) | C32—C31—H31B | 108.2 |
C3i—C2—C1 | 121.0 (5) | N11—C31—H31B | 108.2 |
C3i—C2—S2 | 122.7 (4) | H31A—C31—H31B | 107.4 |
C1—C2—S2 | 116.3 (4) | C31—C32—C33 | 110.2 (5) |
C2i—C3—C4 | 119.8 (6) | C31—C32—H32A | 109.6 |
C2i—C3—S1 | 123.5 (5) | C33—C32—H32A | 109.6 |
C4—C3—S1 | 116.7 (5) | C31—C32—H32B | 109.6 |
N1—C4—C3 | 178.4 (9) | C33—C32—H32B | 109.6 |
N11—C11—C12 | 115.8 (5) | H32A—C32—H32B | 108.1 |
N11—C11—H11A | 108.3 | C32—C33—C34 | 112.6 (6) |
C12—C11—H11A | 108.3 | C32—C33—H33A | 109.1 |
N11—C11—H11B | 108.3 | C34—C33—H33A | 109.1 |
C12—C11—H11B | 108.3 | C32—C33—H33B | 109.1 |
H11A—C11—H11B | 107.4 | C34—C33—H33B | 109.1 |
C11—C12—C13 | 111.3 (6) | H33A—C33—H33B | 107.8 |
C11—C12—H12A | 109.4 | C33—C34—H34A | 109.5 |
C13—C12—H12A | 109.4 | C33—C34—H34B | 109.5 |
C11—C12—H12B | 109.4 | H34A—C34—H34B | 109.5 |
C13—C12—H12B | 109.4 | C33—C34—H34C | 109.5 |
H12A—C12—H12B | 108.0 | H34A—C34—H34C | 109.5 |
C14—C13—C12 | 113.0 (7) | H34B—C34—H34C | 109.5 |
C14—C13—H13A | 109.0 | C42—C41—N11 | 116.3 (4) |
C12—C13—H13A | 109.0 | C42—C41—H41A | 108.2 |
C14—C13—H13B | 109.0 | N11—C41—H41A | 108.2 |
C12—C13—H13B | 109.0 | C42—C41—H41B | 108.2 |
H13A—C13—H13B | 107.8 | N11—C41—H41B | 108.2 |
C13—C14—H14A | 109.5 | H41A—C41—H41B | 107.4 |
C13—C14—H14B | 109.5 | C41—C42—C43 | 111.3 (5) |
H14A—C14—H14B | 109.5 | C41—C42—H42A | 109.4 |
C13—C14—H14C | 109.5 | C43—C42—H42A | 109.4 |
H14A—C14—H14C | 109.5 | C41—C42—H42B | 109.4 |
H14B—C14—H14C | 109.5 | C43—C42—H42B | 109.4 |
N11—C21—C22 | 116.1 (5) | H42A—C42—H42B | 108.0 |
N11—C21—H21A | 108.3 | C44—C43—C42 | 112.7 (6) |
C22—C21—H21A | 108.3 | C44—C43—H43A | 109.1 |
N11—C21—H21B | 108.3 | C42—C43—H43A | 109.1 |
C22—C21—H21B | 108.3 | C44—C43—H43B | 109.1 |
H21A—C21—H21B | 107.4 | C42—C43—H43B | 109.1 |
C23—C22—C21 | 113.0 (5) | H43A—C43—H43B | 107.8 |
C23—C22—H22A | 109.0 | C43—C44—H44A | 109.5 |
C21—C22—H22A | 109.0 | C43—C44—H44B | 109.5 |
C23—C22—H22B | 109.0 | H44A—C44—H44B | 109.5 |
C21—C22—H22B | 109.0 | C43—C44—H44C | 109.5 |
H22A—C22—H22B | 107.8 | H44A—C44—H44C | 109.5 |
C22—C23—C24 | 115.7 (6) | H44B—C44—H44C | 109.5 |
Symmetry code: (i) −x+3, −y−2, −z+3. |