In the title compound, [Pd(C7H12N2)4]Cl2·2CH2Cl2, the Pd atom lies on an inversion center and has a square-planar coordination involving the S atoms of the four 1-tert-butyl-imidazoline-2(3H)-thione ligands. The two chloride ions are not involved in coordination, but are engaged in hydrogen bonding.
Supporting information
CCDC reference: 239117
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.007 Å
- R factor = 0.044
- wR factor = 0.106
- Data-to-parameter ratio = 17.6
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors .... C15
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Tetrakis[1-
tert-butyl-1
H-imidazole-2(3
H)-thione-
κS]palladium(II) dichloride dichloromethane disolvate
top
Crystal data top
[Pd(C7H12N2)4]l2·2CH2Cl2 | F(000) = 1000 |
Mr = 972.14 | Dx = 1.473 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 7773 reflections |
a = 9.3724 (2) Å | θ = 1.9–25.2° |
b = 21.9527 (4) Å | µ = 1.01 mm−1 |
c = 11.4474 (2) Å | T = 293 K |
β = 111.493 (1)° | Block, red |
V = 2191.51 (7) Å3 | 0.48 × 0.32 × 0.10 mm |
Z = 2 | |
Data collection top
Siemens SMART CCD area-detector diffractometer | 3927 independent reflections |
Radiation source: fine-focus sealed tube | 3378 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
φ and ω scans | θmax = 25.2°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→11 |
Tmin = 0.685, Tmax = 0.904 | k = −16→26 |
11352 measured reflections | l = −13→13 |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.106 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0401P)2 + 4.8056P] where P = (Fo2 + 2Fc2)/3 |
3927 reflections | (Δ/σ)max = 0.001 |
223 parameters | Δρmax = 0.57 e Å−3 |
0 restraints | Δρmin = −0.97 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Pd1 | 0.5000 | 0.5000 | 0.5000 | 0.03574 (13) | |
S1 | 0.75992 (12) | 0.51230 (5) | 0.54211 (11) | 0.0530 (3) | |
S2 | 0.51971 (12) | 0.39949 (4) | 0.56852 (8) | 0.0422 (2) | |
Cl1 | 0.1490 (2) | 0.27944 (9) | 0.35042 (17) | 0.1009 (5) | |
Cl2 | 0.0167 (4) | 0.34124 (18) | 0.1183 (3) | 0.2114 (16) | |
Cl3 | 0.50597 (14) | 0.40002 (5) | 0.21970 (11) | 0.0611 (3) | |
N1 | 0.9638 (3) | 0.41683 (15) | 0.6436 (3) | 0.0463 (8) | |
N2 | 0.8010 (4) | 0.40199 (15) | 0.4560 (3) | 0.0502 (8) | |
N3 | 0.5672 (3) | 0.36214 (14) | 0.8103 (3) | 0.0381 (7) | |
N4 | 0.5508 (4) | 0.45935 (14) | 0.7834 (3) | 0.0418 (7) | |
C1 | 0.8432 (4) | 0.44165 (17) | 0.5511 (4) | 0.0428 (9) | |
C2 | 0.9940 (5) | 0.3612 (2) | 0.6013 (5) | 0.0629 (13) | |
C3 | 0.8931 (5) | 0.3523 (2) | 0.4869 (5) | 0.0610 (12) | |
C4 | 1.0509 (5) | 0.4435 (2) | 0.7707 (4) | 0.0523 (10) | |
C5 | 1.1725 (6) | 0.3981 (3) | 0.8454 (5) | 0.0817 (16) | |
C6 | 1.1274 (6) | 0.5018 (2) | 0.7535 (5) | 0.0683 (13) | |
C7 | 0.9389 (6) | 0.4537 (3) | 0.8363 (4) | 0.0713 (14) | |
C8 | 0.5449 (4) | 0.40710 (15) | 0.7234 (3) | 0.0340 (7) | |
C9 | 0.5893 (5) | 0.3892 (2) | 0.9249 (4) | 0.0527 (11) | |
C10 | 0.5797 (5) | 0.4492 (2) | 0.9070 (4) | 0.0532 (11) | |
C11 | 0.5709 (5) | 0.29471 (17) | 0.7876 (4) | 0.0441 (9) | |
C12 | 0.5845 (6) | 0.2613 (2) | 0.9077 (4) | 0.0656 (13) | |
C13 | 0.7092 (5) | 0.2807 (2) | 0.7533 (4) | 0.0565 (11) | |
C14 | 0.4212 (5) | 0.27542 (19) | 0.6840 (4) | 0.0596 (12) | |
C15 | 0.1554 (7) | 0.3434 (3) | 0.2638 (7) | 0.103 (2) | |
H2A | 0.7264 | 0.4072 | 0.3856 | 0.060* | |
H2B | 1.0721 | 0.3346 | 0.6458 | 0.075* | |
H3A | 0.8865 | 0.3183 | 0.4368 | 0.073* | |
H4A | 0.5381 | 0.4947 | 0.7488 | 0.050* | |
H5A | 1.1238 | 0.3614 | 0.8573 | 0.123* | |
H5B | 1.2320 | 0.4152 | 0.9256 | 0.123* | |
H5C | 1.2384 | 0.3889 | 0.8003 | 0.123* | |
H6A | 1.0505 | 0.5306 | 0.7069 | 0.102* | |
H6B | 1.1937 | 0.4932 | 0.7085 | 0.102* | |
H6C | 1.1865 | 0.5186 | 0.8342 | 0.102* | |
H7A | 0.8633 | 0.4831 | 0.7903 | 0.107* | |
H7B | 0.9931 | 0.4685 | 0.9198 | 0.107* | |
H7C | 0.8892 | 0.4159 | 0.8404 | 0.107* | |
H9A | 0.6076 | 0.3692 | 1.0006 | 0.063* | |
H10A | 0.5906 | 0.4788 | 0.9679 | 0.064* | |
H12A | 0.6785 | 0.2727 | 0.9736 | 0.098* | |
H12B | 0.5843 | 0.2181 | 0.8939 | 0.098* | |
H12C | 0.4994 | 0.2719 | 0.9312 | 0.098* | |
H13A | 0.7000 | 0.3020 | 0.6776 | 0.085* | |
H13B | 0.7142 | 0.2377 | 0.7405 | 0.085* | |
H13C | 0.8008 | 0.2937 | 0.8201 | 0.085* | |
H14A | 0.4108 | 0.2962 | 0.6076 | 0.089* | |
H14B | 0.3363 | 0.2857 | 0.7082 | 0.089* | |
H14C | 0.4224 | 0.2322 | 0.6712 | 0.089* | |
H15A | 0.1421 | 0.3796 | 0.3074 | 0.123* | |
H15B | 0.2550 | 0.3458 | 0.2564 | 0.123* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Pd1 | 0.0464 (2) | 0.0260 (2) | 0.0331 (2) | 0.00232 (16) | 0.01250 (16) | 0.00382 (15) |
S2 | 0.0655 (6) | 0.0266 (4) | 0.0352 (5) | 0.0029 (4) | 0.0193 (4) | 0.0039 (4) |
Cl3 | 0.0716 (7) | 0.0438 (6) | 0.0562 (6) | −0.0059 (5) | 0.0094 (5) | −0.0059 (5) |
S1 | 0.0490 (6) | 0.0360 (5) | 0.0686 (7) | −0.0013 (4) | 0.0153 (5) | −0.0037 (5) |
Cl1 | 0.0954 (11) | 0.1065 (13) | 0.1058 (12) | 0.0117 (9) | 0.0429 (10) | −0.0049 (10) |
N4 | 0.0450 (18) | 0.0376 (17) | 0.0415 (17) | 0.0034 (14) | 0.0142 (14) | −0.0023 (14) |
N3 | 0.0423 (17) | 0.0386 (17) | 0.0340 (15) | 0.0057 (13) | 0.0145 (13) | 0.0048 (13) |
C8 | 0.0349 (18) | 0.0316 (18) | 0.0345 (18) | 0.0032 (14) | 0.0114 (15) | 0.0018 (15) |
N1 | 0.0355 (16) | 0.0424 (18) | 0.057 (2) | −0.0001 (14) | 0.0128 (15) | −0.0106 (16) |
N2 | 0.0483 (19) | 0.0444 (19) | 0.053 (2) | −0.0042 (16) | 0.0134 (16) | −0.0128 (16) |
C11 | 0.051 (2) | 0.037 (2) | 0.045 (2) | 0.0051 (17) | 0.0188 (18) | 0.0115 (17) |
C1 | 0.039 (2) | 0.036 (2) | 0.052 (2) | −0.0010 (16) | 0.0144 (18) | −0.0053 (17) |
C9 | 0.055 (2) | 0.071 (3) | 0.0322 (19) | 0.010 (2) | 0.0158 (18) | 0.0009 (19) |
C14 | 0.065 (3) | 0.039 (2) | 0.068 (3) | −0.004 (2) | 0.015 (2) | 0.010 (2) |
C10 | 0.050 (2) | 0.065 (3) | 0.043 (2) | 0.005 (2) | 0.0156 (19) | −0.016 (2) |
C4 | 0.040 (2) | 0.057 (3) | 0.054 (2) | −0.0051 (19) | 0.0094 (19) | −0.008 (2) |
C3 | 0.055 (3) | 0.051 (3) | 0.074 (3) | 0.000 (2) | 0.021 (2) | −0.025 (2) |
C2 | 0.047 (2) | 0.050 (3) | 0.085 (3) | 0.008 (2) | 0.017 (2) | −0.017 (2) |
C13 | 0.065 (3) | 0.045 (2) | 0.064 (3) | 0.018 (2) | 0.028 (2) | 0.013 (2) |
C7 | 0.064 (3) | 0.095 (4) | 0.052 (3) | −0.009 (3) | 0.017 (2) | −0.011 (3) |
C6 | 0.058 (3) | 0.064 (3) | 0.072 (3) | −0.023 (2) | 0.011 (2) | −0.016 (3) |
C12 | 0.082 (3) | 0.059 (3) | 0.059 (3) | 0.011 (2) | 0.029 (3) | 0.029 (2) |
C5 | 0.061 (3) | 0.083 (4) | 0.077 (4) | 0.003 (3) | −0.005 (3) | 0.002 (3) |
Cl2 | 0.192 (3) | 0.243 (4) | 0.132 (2) | −0.029 (3) | −0.020 (2) | 0.065 (2) |
C15 | 0.088 (4) | 0.059 (3) | 0.157 (7) | −0.009 (3) | 0.040 (4) | −0.037 (4) |
Geometric parameters (Å, º) top
Pd1—S1 | 2.3193 (11) | C14—H14C | 0.9600 |
Pd1—S1i | 2.3193 (11) | C10—H10A | 0.9300 |
Pd1—S2i | 2.3263 (9) | C4—C7 | 1.514 (6) |
Pd1—S2 | 2.3263 (9) | C4—C6 | 1.515 (6) |
Pd1—Cl3 | 3.9048 (11) | C4—C5 | 1.521 (6) |
S2—C8 | 1.709 (3) | C3—C2 | 1.318 (6) |
S1—C1 | 1.723 (4) | C3—H3A | 0.9300 |
Cl1—C15 | 1.732 (7) | C2—H2B | 0.9300 |
N4—C8 | 1.328 (4) | C13—H13A | 0.9600 |
N4—C10 | 1.358 (5) | C13—H13B | 0.9600 |
N4—H4A | 0.8600 | C13—H13C | 0.9600 |
N3—C8 | 1.362 (4) | C7—H7A | 0.9600 |
N3—C9 | 1.385 (5) | C7—H7B | 0.9600 |
N3—C11 | 1.505 (5) | C7—H7C | 0.9600 |
N1—C1 | 1.348 (5) | C6—H6A | 0.9600 |
N1—C2 | 1.380 (5) | C6—H6B | 0.9600 |
N1—C4 | 1.502 (5) | C6—H6C | 0.9600 |
N2—C1 | 1.336 (5) | C12—H12A | 0.9600 |
N2—C3 | 1.354 (6) | C12—H12B | 0.9600 |
N2—H2A | 0.8600 | C12—H12C | 0.9600 |
C11—C13 | 1.517 (6) | C5—H5A | 0.9600 |
C11—C14 | 1.528 (6) | C5—H5B | 0.9600 |
C11—C12 | 1.521 (5) | C5—H5C | 0.9600 |
C9—C10 | 1.331 (6) | Cl2—C15 | 1.697 (7) |
C9—H9A | 0.9300 | C15—H15A | 0.9700 |
C14—H14A | 0.9600 | C15—H15B | 0.9700 |
C14—H14B | 0.9600 | | |
| | | |
S1—Pd1—S1i | 180.00 (6) | N4—C10—H10A | 126.3 |
S1—Pd1—S2i | 84.68 (4) | N1—C4—C7 | 108.0 (3) |
S1i—Pd1—S2i | 95.32 (4) | N1—C4—C6 | 108.6 (4) |
S1—Pd1—S2 | 95.32 (4) | C7—C4—C6 | 112.8 (4) |
S1i—Pd1—S2 | 84.68 (4) | N1—C4—C5 | 108.5 (4) |
S2i—Pd1—S2 | 180.000 (14) | C7—C4—C5 | 109.4 (4) |
S1—Pd1—Cl3 | 84.61 (3) | C6—C4—C5 | 109.5 (4) |
S1i—Pd1—Cl3 | 95.39 (3) | C2—C3—N2 | 107.2 (4) |
S2i—Pd1—Cl3 | 106.22 (3) | C2—C3—H3A | 126.4 |
S2—Pd1—Cl3 | 73.78 (3) | N2—C3—H3A | 126.4 |
C8—S2—Pd1 | 102.76 (12) | C3—C2—N1 | 108.4 (4) |
C1—S1—Pd1 | 109.04 (13) | C11—C13—H13A | 109.5 |
C8—N4—C10 | 110.6 (3) | C11—C13—H13B | 109.5 |
C8—N4—H4A | 124.7 | H13A—C13—H13B | 109.5 |
C10—N4—H4A | 124.7 | C11—C13—H13C | 109.5 |
C8—N3—C9 | 108.1 (3) | H13A—C13—H13C | 109.5 |
C8—N3—C11 | 126.4 (3) | H13B—C13—H13C | 109.5 |
C9—N3—C11 | 125.5 (3) | C4—C7—H7A | 109.5 |
N4—C8—N3 | 106.4 (3) | C4—C7—H7B | 109.5 |
N4—C8—S2 | 125.8 (3) | H7A—C7—H7B | 109.5 |
N3—C8—S2 | 127.8 (3) | C4—C7—H7C | 109.5 |
C1—N1—C2 | 107.6 (3) | H7A—C7—H7C | 109.5 |
C1—N1—C4 | 127.2 (3) | H7B—C7—H7C | 109.5 |
C2—N1—C4 | 125.2 (4) | C4—C6—H6A | 109.5 |
C1—N2—C3 | 110.0 (4) | C4—C6—H6B | 109.5 |
C1—N2—H2A | 125.0 | H6A—C6—H6B | 109.5 |
C3—N2—H2A | 125.0 | C4—C6—H6C | 109.5 |
N3—C11—C13 | 108.6 (3) | H6A—C6—H6C | 109.5 |
N3—C11—C14 | 109.5 (3) | H6B—C6—H6C | 109.5 |
C13—C11—C14 | 111.8 (4) | C11—C12—H12A | 109.5 |
N3—C11—C12 | 108.6 (3) | C11—C12—H12B | 109.5 |
C13—C11—C12 | 109.8 (3) | H12A—C12—H12B | 109.5 |
C14—C11—C12 | 108.5 (4) | C11—C12—H12C | 109.5 |
N2—C1—N1 | 106.8 (3) | H12A—C12—H12C | 109.5 |
N2—C1—S1 | 123.1 (3) | H12B—C12—H12C | 109.5 |
N1—C1—S1 | 130.0 (3) | C4—C5—H5A | 109.5 |
C10—C9—N3 | 107.5 (4) | C4—C5—H5B | 109.5 |
C10—C9—H9A | 126.2 | H5A—C5—H5B | 109.5 |
N3—C9—H9A | 126.2 | C4—C5—H5C | 109.5 |
C11—C14—H14A | 109.5 | H5A—C5—H5C | 109.5 |
C11—C14—H14B | 109.5 | H5B—C5—H5C | 109.5 |
H14A—C14—H14B | 109.5 | Cl2—C15—Cl1 | 111.4 (3) |
C11—C14—H14C | 109.5 | Cl2—C15—H15A | 109.3 |
H14A—C14—H14C | 109.5 | Cl1—C15—H15A | 109.3 |
H14B—C14—H14C | 109.5 | Cl2—C15—H15B | 109.3 |
C9—C10—N4 | 107.4 (4) | Cl1—C15—H15B | 109.3 |
C9—C10—H10A | 126.3 | H15A—C15—H15B | 108.0 |
| | | |
S1—Pd1—S2—C8 | 91.02 (13) | C3—N2—C1—S1 | 175.8 (3) |
S1i—Pd1—S2—C8 | −88.98 (13) | C2—N1—C1—N2 | 0.4 (5) |
S2—Pd1—S2—C8 | 20.04 (15) | C4—N1—C1—N2 | −179.1 (4) |
Cl3i—Pd1—S2—C8 | −6.19 (15) | C2—N1—C1—S1 | −174.9 (3) |
S2i—Pd1—S1—C1 | −159.70 (15) | C4—N1—C1—S1 | 5.6 (6) |
S2—Pd1—S1—C1 | 20.30 (15) | Pd1—S1—C1—N2 | 59.8 (4) |
Cl3—Pd1—S1—C1 | −52.81 (15) | Pd1—S1—C1—N1 | −125.5 (4) |
C10—N4—C8—N3 | 1.4 (4) | C8—N3—C9—C10 | 0.3 (5) |
C10—N4—C8—S2 | −176.9 (3) | C11—N3—C9—C10 | 179.1 (4) |
C9—N3—C8—N4 | −1.0 (4) | N3—C9—C10—N4 | 0.5 (5) |
C11—N3—C8—N4 | −179.8 (3) | C8—N4—C10—C9 | −1.2 (5) |
C9—N3—C8—S2 | 177.2 (3) | C1—N1—C4—C7 | 58.9 (6) |
C11—N3—C8—S2 | −1.5 (5) | C2—N1—C4—C7 | −120.5 (5) |
Pd1—S2—C8—N4 | −0.1 (3) | C1—N1—C4—C6 | −63.6 (5) |
Pd1—S2—C8—N3 | −178.0 (3) | C2—N1—C4—C6 | 116.9 (5) |
C8—N3—C11—C13 | 65.6 (5) | C1—N1—C4—C5 | 177.4 (4) |
C9—N3—C11—C13 | −112.9 (4) | C2—N1—C4—C5 | −2.1 (6) |
C8—N3—C11—C14 | −56.8 (5) | C1—N2—C3—C2 | −0.5 (5) |
C9—N3—C11—C14 | 124.7 (4) | N2—C3—C2—N1 | 0.8 (6) |
C8—N3—C11—C12 | −175.0 (4) | C1—N1—C2—C3 | −0.8 (5) |
C9—N3—C11—C12 | 6.5 (5) | C4—N1—C2—C3 | 178.8 (4) |
C3—N2—C1—N1 | 0.0 (5) | | |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2a···Cl3 | 0.86 | 2.24 | 3.080 (4) | 165 |
N4—H4a···Cl3i | 0.86 | 2.40 | 3.131 (3) | 143 |
Symmetry code: (i) −x+1, −y+1, −z+1. |