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In the title compound, [PdCl2(C18H14S2)], the two Cl atoms and the two S atoms are in a slightly disorted square-planar arrangement around the Pd atom. The two phenyl groups are on the same side of the PdCl2S2 plane. Close contacts between the Cl and S atoms suggest weak intermolecular interactions.
Supporting information
CCDC reference: 277727
Key indicators
- Single-crystal X-ray study
- T = 103 K
- Mean (C-C) = 0.003 Å
- R factor = 0.017
- wR factor = 0.043
- Data-to-parameter ratio = 15.0
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Pd1 - S2 .. 5.20 su
PLAT431_ALERT_2_C Short Inter HL..A Contact Cl1 .. S2 .. 3.53 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact Cl2 .. S1 .. 3.33 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CrystalClear (Rigaku, 2004); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: DIRDIF99 (Beurskens et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97.
dichloro[1,2-bis(phenylsulfanyl)benzene]palladium
top
Crystal data top
[PdCl2(C18H14S2)] | Z = 2 |
Mr = 471.71 | F(000) = 468 |
Triclinic, P1 | Dx = 1.787 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71070 Å |
a = 9.9145 (14) Å | Cell parameters from 3041 reflections |
b = 10.214 (2) Å | θ = 3.0–25.5° |
c = 10.521 (2) Å | µ = 1.60 mm−1 |
α = 76.905 (10)° | T = 103 K |
β = 63.051 (9)° | Prism, orange |
γ = 67.639 (10)° | 0.45 × 0.30 × 0.28 mm |
V = 876.4 (3) Å3 | |
Data collection top
Rigaku Mercury diffractometer | 3140 independent reflections |
Radiation source: fine-focus sealed tube | 2982 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.012 |
Detector resolution: 7.31 pixels mm-1 | θmax = 25.5°, θmin = 3.0° |
ω scans | h = −10→12 |
Absorption correction: multi-scan (Jacobson, 1998) | k = −12→12 |
Tmin = 0.534, Tmax = 0.646 | l = −9→12 |
5768 measured reflections | |
Refinement top
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)] = 0.017 | H-atom parameters constrained |
wR(F2) = 0.043 | w = 1/[σ2(Fo2) + (0.0179P)2 + 0.6226P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max = 0.002 |
3140 reflections | Δρmax = 0.34 e Å−3 |
209 parameters | Δρmin = −0.47 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0058 (6) |
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 | x | y | z | Uiso*/Ueq | |
Pd1 | 0.160038 (16) | 0.351156 (13) | 0.983833 (13) | 0.00798 (7) | |
Cl1 | 0.04224 (6) | 0.23695 (5) | 1.20125 (5) | 0.01444 (11) | |
Cl2 | 0.21687 (5) | 0.49290 (4) | 1.08310 (5) | 0.01212 (10) | |
S1 | 0.10134 (5) | 0.21948 (5) | 0.88101 (5) | 0.00895 (10) | |
S2 | 0.28534 (5) | 0.44949 (5) | 0.76502 (5) | 0.00928 (10) | |
C1 | 0.1561 (2) | 0.29199 (19) | 0.69950 (19) | 0.0106 (4) | |
C2 | 0.1229 (2) | 0.2452 (2) | 0.6058 (2) | 0.0149 (4) | |
H1 | 0.0820 | 0.1680 | 0.6345 | 0.018* | |
C3 | 0.1498 (2) | 0.3121 (2) | 0.4703 (2) | 0.0183 (4) | |
H2 | 0.1304 | 0.2787 | 0.4050 | 0.022* | |
C4 | 0.2049 (2) | 0.4278 (2) | 0.4299 (2) | 0.0175 (4) | |
H3 | 0.2188 | 0.4755 | 0.3383 | 0.021* | |
C5 | 0.2396 (2) | 0.4740 (2) | 0.5219 (2) | 0.0145 (4) | |
H4 | 0.2774 | 0.5531 | 0.4942 | 0.017* | |
C6 | 0.2185 (2) | 0.40306 (19) | 0.65582 (19) | 0.0106 (4) | |
C7 | 0.2427 (2) | 0.04404 (19) | 0.86291 (19) | 0.0109 (4) | |
C8 | 0.1953 (2) | −0.0608 (2) | 0.8468 (2) | 0.0141 (4) | |
H5 | 0.0941 | −0.0374 | 0.8444 | 0.017* | |
C9 | 0.2972 (2) | −0.1998 (2) | 0.8343 (2) | 0.0172 (4) | |
H6 | 0.2665 | −0.2722 | 0.8223 | 0.021* | |
C10 | 0.4437 (2) | −0.2325 (2) | 0.8393 (2) | 0.0178 (4) | |
H7 | 0.5128 | −0.3278 | 0.8317 | 0.021* | |
C11 | 0.4909 (2) | −0.1276 (2) | 0.8553 (2) | 0.0170 (4) | |
H8 | 0.5922 | −0.1511 | 0.8576 | 0.020* | |
C12 | 0.3894 (2) | 0.0122 (2) | 0.8679 (2) | 0.0140 (4) | |
H9 | 0.4201 | 0.0846 | 0.8797 | 0.017* | |
C13 | 0.4855 (2) | 0.32451 (19) | 0.71152 (19) | 0.0110 (4) | |
C14 | 0.5671 (2) | 0.3127 (2) | 0.7943 (2) | 0.0156 (4) | |
H10 | 0.5192 | 0.3709 | 0.8721 | 0.019* | |
C15 | 0.7185 (2) | 0.2154 (2) | 0.7619 (2) | 0.0204 (4) | |
H11 | 0.7742 | 0.2055 | 0.8187 | 0.024* | |
C16 | 0.7896 (2) | 0.1318 (2) | 0.6464 (2) | 0.0227 (5) | |
H12 | 0.8928 | 0.0637 | 0.6256 | 0.027* | |
C17 | 0.7098 (2) | 0.1481 (2) | 0.5620 (2) | 0.0214 (5) | |
H13 | 0.7602 | 0.0932 | 0.4814 | 0.026* | |
C18 | 0.5569 (2) | 0.2437 (2) | 0.5939 (2) | 0.0158 (4) | |
H14 | 0.5018 | 0.2539 | 0.5364 | 0.019* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Pd1 | 0.00908 (10) | 0.00771 (9) | 0.00704 (9) | −0.00171 (6) | −0.00356 (6) | −0.00142 (5) |
Cl1 | 0.0172 (3) | 0.0182 (2) | 0.0091 (2) | −0.00876 (19) | −0.00512 (19) | 0.00186 (17) |
Cl2 | 0.0155 (2) | 0.0112 (2) | 0.0120 (2) | −0.00241 (18) | −0.00774 (19) | −0.00375 (17) |
S1 | 0.0092 (2) | 0.0080 (2) | 0.0098 (2) | −0.00266 (17) | −0.00358 (18) | −0.00151 (16) |
S2 | 0.0114 (2) | 0.0084 (2) | 0.0091 (2) | −0.00368 (18) | −0.00445 (18) | −0.00094 (16) |
C1 | 0.0085 (9) | 0.0112 (9) | 0.0094 (9) | 0.0014 (7) | −0.0043 (8) | −0.0028 (7) |
C2 | 0.0123 (10) | 0.0147 (9) | 0.0196 (10) | −0.0019 (8) | −0.0075 (8) | −0.0068 (8) |
C3 | 0.0147 (11) | 0.0248 (11) | 0.0171 (10) | 0.0007 (8) | −0.0093 (9) | −0.0105 (8) |
C4 | 0.0124 (11) | 0.0232 (10) | 0.0108 (9) | 0.0019 (8) | −0.0048 (8) | −0.0033 (8) |
C5 | 0.0113 (10) | 0.0152 (9) | 0.0129 (9) | −0.0018 (8) | −0.0040 (8) | −0.0002 (7) |
C6 | 0.0081 (9) | 0.0128 (9) | 0.0098 (9) | −0.0001 (7) | −0.0038 (7) | −0.0043 (7) |
C7 | 0.0114 (10) | 0.0087 (9) | 0.0093 (9) | −0.0022 (7) | −0.0022 (8) | −0.0009 (7) |
C8 | 0.0133 (10) | 0.0140 (9) | 0.0148 (9) | −0.0051 (8) | −0.0050 (8) | −0.0009 (7) |
C9 | 0.0224 (11) | 0.0116 (9) | 0.0176 (10) | −0.0071 (8) | −0.0061 (9) | −0.0026 (8) |
C10 | 0.0192 (11) | 0.0103 (9) | 0.0161 (10) | 0.0015 (8) | −0.0052 (9) | −0.0019 (8) |
C11 | 0.0121 (10) | 0.0175 (10) | 0.0181 (10) | −0.0015 (8) | −0.0069 (9) | 0.0008 (8) |
C12 | 0.0148 (10) | 0.0128 (9) | 0.0149 (9) | −0.0060 (8) | −0.0056 (8) | 0.0003 (7) |
C13 | 0.0082 (9) | 0.0107 (9) | 0.0122 (9) | −0.0047 (7) | −0.0019 (8) | 0.0008 (7) |
C14 | 0.0148 (11) | 0.0201 (10) | 0.0116 (9) | −0.0077 (8) | −0.0029 (8) | −0.0018 (8) |
C15 | 0.0133 (11) | 0.0290 (11) | 0.0191 (10) | −0.0061 (9) | −0.0081 (9) | 0.0001 (9) |
C16 | 0.0108 (11) | 0.0238 (11) | 0.0276 (12) | −0.0014 (9) | −0.0048 (9) | −0.0049 (9) |
C17 | 0.0163 (11) | 0.0220 (11) | 0.0227 (11) | −0.0044 (9) | −0.0026 (9) | −0.0104 (9) |
C18 | 0.0148 (10) | 0.0178 (10) | 0.0167 (10) | −0.0066 (8) | −0.0057 (8) | −0.0040 (8) |
Geometric parameters (Å, º) top
Pd1—S1 | 2.2679 (5) | C7—C8 | 1.389 (3) |
Pd1—S2 | 2.2719 (6) | C8—C9 | 1.388 (3) |
Pd1—Cl2 | 2.3116 (5) | C8—H5 | 0.9500 |
Pd1—Cl1 | 2.3159 (6) | C9—C10 | 1.384 (3) |
S1—C7 | 1.7924 (18) | C9—H6 | 0.9500 |
S1—C1 | 1.7932 (19) | C10—C11 | 1.390 (3) |
S1—Cl2i | 3.3311 (9) | C10—H7 | 0.9500 |
S2—C6 | 1.7774 (18) | C11—C12 | 1.393 (3) |
S2—C13 | 1.8085 (19) | C11—H8 | 0.9500 |
S2—Cl1i | 3.5338 (9) | C12—H9 | 0.9500 |
C1—C6 | 1.386 (3) | C13—C18 | 1.392 (3) |
C1—C2 | 1.391 (3) | C13—C14 | 1.394 (3) |
C2—C3 | 1.387 (3) | C14—C15 | 1.383 (3) |
C2—H1 | 0.9500 | C14—H10 | 0.9500 |
C3—C4 | 1.389 (3) | C15—C16 | 1.392 (3) |
C3—H2 | 0.9500 | C15—H11 | 0.9500 |
C4—C5 | 1.383 (3) | C16—C17 | 1.383 (3) |
C4—H3 | 0.9500 | C16—H12 | 0.9500 |
C5—C6 | 1.393 (3) | C17—C18 | 1.388 (3) |
C5—H4 | 0.9500 | C17—H13 | 0.9500 |
C7—C12 | 1.388 (3) | C18—H14 | 0.9500 |
| | | |
S1—Pd1—S2 | 89.86 (2) | C12—C7—C8 | 121.26 (17) |
S1—Pd1—Cl2 | 177.782 (16) | C12—C7—S1 | 122.77 (14) |
S2—Pd1—Cl2 | 88.56 (2) | C8—C7—S1 | 115.96 (14) |
S1—Pd1—Cl1 | 87.95 (2) | C9—C8—C7 | 119.44 (18) |
S2—Pd1—Cl1 | 176.378 (17) | C9—C8—H5 | 120.3 |
Cl2—Pd1—Cl1 | 93.70 (2) | C7—C8—H5 | 120.3 |
C7—S1—C1 | 102.47 (8) | C10—C9—C8 | 119.65 (18) |
C7—S1—Pd1 | 109.26 (6) | C10—C9—H6 | 120.2 |
C1—S1—Pd1 | 103.51 (6) | C8—C9—H6 | 120.2 |
C7—S1—Cl2i | 166.57 (6) | C9—C10—C11 | 120.85 (18) |
C1—S1—Cl2i | 79.63 (6) | C9—C10—H7 | 119.6 |
Pd1—S1—Cl2i | 82.80 (2) | C11—C10—H7 | 119.6 |
C6—S2—C13 | 100.23 (9) | C10—C11—C12 | 119.82 (18) |
C6—S2—Pd1 | 102.86 (6) | C10—C11—H8 | 120.1 |
C13—S2—Pd1 | 101.01 (6) | C12—C11—H8 | 120.1 |
C6—S2—Cl1i | 83.45 (6) | C7—C12—C11 | 118.98 (18) |
C13—S2—Cl1i | 162.70 (6) | C7—C12—H9 | 120.5 |
Pd1—S2—Cl1i | 94.54 (2) | C11—C12—H9 | 120.5 |
C6—C1—C2 | 119.81 (17) | C18—C13—C14 | 120.88 (18) |
C6—C1—S1 | 120.08 (14) | C18—C13—S2 | 122.61 (15) |
C2—C1—S1 | 119.87 (15) | C14—C13—S2 | 116.51 (14) |
C3—C2—C1 | 119.60 (18) | C15—C14—C13 | 119.27 (18) |
C3—C2—H1 | 120.2 | C15—C14—H10 | 120.4 |
C1—C2—H1 | 120.2 | C13—C14—H10 | 120.4 |
C2—C3—C4 | 120.21 (18) | C14—C15—C16 | 120.34 (19) |
C2—C3—H2 | 119.9 | C14—C15—H11 | 119.8 |
C4—C3—H2 | 119.9 | C16—C15—H11 | 119.8 |
C5—C4—C3 | 120.49 (18) | C17—C16—C15 | 119.83 (19) |
C5—C4—H3 | 119.8 | C17—C16—H12 | 120.1 |
C3—C4—H3 | 119.8 | C15—C16—H12 | 120.1 |
C4—C5—C6 | 119.10 (18) | C16—C17—C18 | 120.72 (19) |
C4—C5—H4 | 120.5 | C16—C17—H13 | 119.6 |
C6—C5—H4 | 120.5 | C18—C17—H13 | 119.6 |
C1—C6—C5 | 120.65 (17) | C17—C18—C13 | 118.90 (18) |
C1—C6—S2 | 120.43 (14) | C17—C18—H14 | 120.5 |
C5—C6—S2 | 118.79 (15) | C13—C18—H14 | 120.5 |
| | | |
S2—Pd1—S1—C7 | 99.18 (6) | C13—S2—C6—C5 | −91.62 (16) |
Cl1—Pd1—S1—C7 | −77.93 (7) | Pd1—S2—C6—C5 | 164.48 (14) |
S2—Pd1—S1—C1 | −9.44 (6) | Cl1i—S2—C6—C5 | 71.29 (15) |
Cl1—Pd1—S1—C1 | 173.45 (6) | C1—S1—C7—C12 | 90.40 (17) |
S2—Pd1—S1—Cl2i | −86.91 (2) | Pd1—S1—C7—C12 | −18.92 (17) |
Cl1—Pd1—S1—Cl2i | 95.98 (2) | Cl2i—S1—C7—C12 | −171.98 (17) |
S1—Pd1—S2—C6 | 14.66 (6) | C1—S1—C7—C8 | −91.11 (15) |
Cl2—Pd1—S2—C6 | −163.78 (6) | Pd1—S1—C7—C8 | 159.58 (13) |
S1—Pd1—S2—C13 | −88.64 (6) | Cl2i—S1—C7—C8 | 6.5 (4) |
Cl2—Pd1—S2—C13 | 92.92 (6) | C12—C7—C8—C9 | −0.5 (3) |
S1—Pd1—S2—Cl1i | 98.96 (2) | S1—C7—C8—C9 | −179.05 (15) |
Cl2—Pd1—S2—Cl1i | −79.48 (2) | C7—C8—C9—C10 | 0.6 (3) |
C7—S1—C1—C6 | −113.41 (16) | C8—C9—C10—C11 | −0.6 (3) |
Pd1—S1—C1—C6 | 0.21 (16) | C9—C10—C11—C12 | 0.6 (3) |
Cl2i—S1—C1—C6 | 80.13 (15) | C8—C7—C12—C11 | 0.5 (3) |
C7—S1—C1—C2 | 72.25 (16) | S1—C7—C12—C11 | 178.93 (14) |
Pd1—S1—C1—C2 | −174.13 (14) | C10—C11—C12—C7 | −0.6 (3) |
Cl2i—S1—C1—C2 | −94.22 (15) | C6—S2—C13—C18 | 11.13 (17) |
C6—C1—C2—C3 | −1.2 (3) | Pd1—S2—C13—C18 | 116.53 (15) |
S1—C1—C2—C3 | 173.13 (15) | Cl1i—S2—C13—C18 | −89.8 (3) |
C1—C2—C3—C4 | −2.0 (3) | C6—S2—C13—C14 | −169.13 (14) |
C2—C3—C4—C5 | 2.6 (3) | Pd1—S2—C13—C14 | −63.73 (14) |
C3—C4—C5—C6 | 0.0 (3) | Cl1i—S2—C13—C14 | 90.0 (2) |
C2—C1—C6—C5 | 3.8 (3) | C18—C13—C14—C15 | −2.5 (3) |
S1—C1—C6—C5 | −170.53 (14) | S2—C13—C14—C15 | 177.73 (15) |
C2—C1—C6—S2 | −171.97 (14) | C13—C14—C15—C16 | 1.1 (3) |
S1—C1—C6—S2 | 13.7 (2) | C14—C15—C16—C17 | 1.2 (3) |
C4—C5—C6—C1 | −3.2 (3) | C15—C16—C17—C18 | −2.2 (3) |
C4—C5—C6—S2 | 172.68 (15) | C16—C17—C18—C13 | 0.7 (3) |
C13—S2—C6—C1 | 84.25 (16) | C14—C13—C18—C17 | 1.6 (3) |
Pd1—S2—C6—C1 | −19.65 (16) | S2—C13—C18—C17 | −178.65 (15) |
Cl1i—S2—C6—C1 | −112.84 (15) | | |
Symmetry code: (i) −x, −y+1, −z+2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H2···Cl1ii | 0.95 | 2.82 | 3.753 (2) | 169 |
C4—H3···Cl2ii | 0.95 | 2.66 | 3.513 (2) | 150 |
Symmetry code: (ii) x, y, z−1. |
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