metal-organic compounds
(Benzyl isocyanide-κC1)chlorido(2-chloro-3-dimethylamino-1-phenylprop-1-en-1-yl-κ2C1,N)palladium(II)
aInstituto de Fisica de Sao Carlos, Av. do Trabalhador Saocarlense, 400, Sao Carlos, SP, Brazil, and bInstituto de Quimica de Sao Carlos, Av. do Trabalhador Saocarlense, 400, Sao Carlos, SP, Brazil
*Correspondence e-mail: mafud@usp.br
In the title compound, [Pd(C11H13ClN)Cl(C8H7N)], which crystallized in the P212121, the PdII atom is coordinated by two C atoms, a Csp2 atom of the 2-chloro-3-dimethylamino-1-phenylprop-1-en-1-yl ligand and a Csp atom from the benzyl isocyanide ligand, as well as an N atom of the ligand and a Cl atom, in a square-planar geometry. In the complex, there is a short C—H⋯Cl hydrogen bond and a C—H⋯π interaction. In the crystal, molecules are linked via C—H⋯Cl hydrogen bonds, forming chains along the a-axis direction.
Related literature
For the crystal structures of similar compounds, see: Moro et al. (2004); Caires et al. (2006); Mafud et al. (2013).
Experimental
Crystal data
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Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 2012).
Supporting information
https://doi.org/10.1107/S1600536812049768/su2529sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812049768/su2529Isup2.hkl
The title compound is the product of a cleavage reaction. It was obtained from the reaction between the dimer [Pd (DMBA)(µX)]2 [where X = Cl, N3, NCO, and DMBA = 7,12-dimethylbenz(a)anthracene] and thiourea, in a 1:2 stoichiometric ratio in chloroform. The solution was stirred during 1 h and then the mixture was left for the solvent to slowly evaporate at room temperature. Large yellow needle-shaped crystals, suitable for X-ray
were obtained.The C-bound H-atoms were included in calculated positions and treated as riding atoms: C—H = 0.93, 0.96 and 0.97 Å, for CH, CH3 and CH2 H atoms, respectively, with Uiso(H) = k × Ueq(parent C-atom), were k = 1.5 for CH3 H atoms, and = 1.2 for other H atoms.
The title compound was obtained from the reaction between the dimer [Pd(DMBA)(µX)]2 [where X = Cl, N3, NCO, and DMBA = 7,12-dimethylbenz(a)anthracene] and thiourea, being the product of a cleavage reaction. As a palladium complex it could be of interest with respect to anticancer activity.
In the title compound, Fig. 1, the palladium atom coordinates to two C atoms, a Csp2 and a Csp atom [Pd1—C9 2.006 (5) Å, Pd1—C1 1.928 (6) Å, respectively], the amine N atom [Pd1—N2 2.098 (4) Å] and an atom of chlorine [Pd1—Cl1 2.3929 (2) Å], with a square planar geometry. The distances and angles in the title compound are close to those reported for similar compounds (Moro et al., 2004; Caires et al., 2006; Mafud et al., 2013). In the molecule there is a short C-H···Cl contact and a C-H···π interaction (Table 1).
In the crystal, molecules are linked via C-H···Cl hydrogen bonds (Fig. 2 and Table 1) forming chains along the a axis.
For the crystal structures of similar compounds, see: Moro et al. (2004); Caires et al. (2006); Mafud et al. (2013).
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell
CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 2012).[Pd(C11H13ClN)Cl(C8H7N)] | F(000) = 912 |
Mr = 453.67 | Dx = 1.572 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 25 reflections |
a = 6.2529 (7) Å | θ = 11.2–18.2° |
b = 11.0931 (10) Å | µ = 1.25 mm−1 |
c = 27.640 (2) Å | T = 290 K |
V = 1917.2 (3) Å3 | Prism, yellow |
Z = 4 | 0.63 × 0.08 × 0.05 mm |
Enraf–Nonius TurboCAD-4 diffractometer | 2420 reflections with I > 2σ(I) |
Radiation source: Enraf Nonius FR590 | Rint = 0.019 |
Graphite monochromator | θmax = 29.9°, θmin = 2.9° |
non–profiled ω scans | h = −8→1 |
Absorption correction: ψ scan (North et al., 1968) | k = −15→0 |
Tmin = 0.871, Tmax = 0.928 | l = 0→38 |
3421 measured reflections | 3 standard reflections every 120 min |
3358 independent reflections | intensity decay: 1% |
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)] = 0.039 | H-atom parameters constrained |
wR(F2) = 0.085 | w = 1/[σ2(Fo2) + (0.0337P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
3358 reflections | Δρmax = 0.67 e Å−3 |
219 parameters | Δρmin = −1.07 e Å−3 |
0 restraints | Absolute structure: Flack (1983), 161 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.10 (5) |
[Pd(C11H13ClN)Cl(C8H7N)] | V = 1917.2 (3) Å3 |
Mr = 453.67 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 6.2529 (7) Å | µ = 1.25 mm−1 |
b = 11.0931 (10) Å | T = 290 K |
c = 27.640 (2) Å | 0.63 × 0.08 × 0.05 mm |
Enraf–Nonius TurboCAD-4 diffractometer | 2420 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.019 |
Tmin = 0.871, Tmax = 0.928 | 3 standard reflections every 120 min |
3421 measured reflections | intensity decay: 1% |
3358 independent reflections |
R[F2 > 2σ(F2)] = 0.039 | H-atom parameters constrained |
wR(F2) = 0.085 | Δρmax = 0.67 e Å−3 |
S = 1.03 | Δρmin = −1.07 e Å−3 |
3358 reflections | Absolute structure: Flack (1983), 161 Friedel pairs |
219 parameters | Absolute structure parameter: −0.10 (5) |
0 restraints |
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 | ||
Pd1 | 0.69687 (7) | 0.16519 (4) | 0.302107 (14) | 0.03072 (10) | |
Cl2 | 0.1519 (3) | 0.35671 (17) | 0.37641 (6) | 0.0620 (5) | |
Cl1 | 0.9388 (3) | 0.12673 (13) | 0.23683 (5) | 0.0460 (4) | |
N1 | 0.8931 (9) | −0.0511 (5) | 0.35548 (17) | 0.0432 (12) | |
N2 | 0.5455 (8) | 0.3051 (4) | 0.26417 (15) | 0.0336 (11) | |
C1 | 0.8195 (11) | 0.0332 (5) | 0.33801 (18) | 0.0374 (13) | |
C2 | 0.9749 (11) | −0.1613 (6) | 0.3763 (2) | 0.0584 (18) | |
H2A | 1.0798 | −0.1418 | 0.4009 | 0.07* | |
H2B | 1.0462 | −0.2078 | 0.3513 | 0.07* | |
C3 | 0.7989 (12) | −0.2368 (5) | 0.39854 (19) | 0.0420 (13) | |
C4 | 0.6530 (14) | −0.1880 (7) | 0.4296 (2) | 0.062 (2) | |
H4 | 0.6605 | −0.1065 | 0.4373 | 0.075* | |
C5 | 0.4955 (16) | −0.2581 (9) | 0.4496 (3) | 0.084 (3) | |
H5 | 0.3979 | −0.2247 | 0.4712 | 0.1* | |
C6 | 0.4832 (18) | −0.3770 (9) | 0.4377 (3) | 0.087 (3) | |
H6 | 0.3748 | −0.4244 | 0.4507 | 0.104* | |
C7 | 0.6277 (17) | −0.4276 (7) | 0.4068 (3) | 0.082 (3) | |
H7 | 0.6188 | −0.509 | 0.3991 | 0.098* | |
C8 | 0.7869 (14) | −0.3574 (6) | 0.3870 (2) | 0.0608 (19) | |
H8 | 0.886 | −0.3913 | 0.366 | 0.073* | |
C9 | 0.4927 (9) | 0.2110 (5) | 0.35497 (18) | 0.0325 (13) | |
C10 | 0.4966 (9) | 0.1640 (6) | 0.40531 (18) | 0.0364 (12) | |
C11 | 0.6694 (11) | 0.1801 (6) | 0.43592 (19) | 0.0458 (15) | |
H11 | 0.7911 | 0.2193 | 0.4247 | 0.055* | |
C12 | 0.6627 (11) | 0.1380 (6) | 0.4833 (2) | 0.0514 (17) | |
H12 | 0.7784 | 0.1514 | 0.5037 | 0.062* | |
C13 | 0.4896 (14) | 0.0777 (6) | 0.4999 (2) | 0.0551 (19) | |
H13 | 0.4885 | 0.0486 | 0.5314 | 0.066* | |
C14 | 0.3175 (13) | 0.0594 (6) | 0.4709 (2) | 0.0538 (17) | |
H14 | 0.198 | 0.0186 | 0.4825 | 0.065* | |
C15 | 0.3225 (12) | 0.1027 (5) | 0.4235 (2) | 0.0463 (15) | |
H15 | 0.2048 | 0.0898 | 0.4036 | 0.056* | |
C16 | 0.3523 (9) | 0.2918 (5) | 0.3399 (2) | 0.0388 (14) | |
C17 | 0.3425 (9) | 0.3377 (6) | 0.28883 (18) | 0.0449 (14) | |
H17A | 0.2222 | 0.3018 | 0.272 | 0.054* | |
H17B | 0.3242 | 0.4246 | 0.2888 | 0.054* | |
C18 | 0.6951 (13) | 0.4088 (5) | 0.2648 (2) | 0.0585 (18) | |
H18A | 0.6372 | 0.4732 | 0.2457 | 0.088* | |
H18B | 0.8305 | 0.3845 | 0.2517 | 0.088* | |
H18C | 0.7144 | 0.4359 | 0.2975 | 0.088* | |
C19 | 0.4974 (12) | 0.2744 (6) | 0.21329 (19) | 0.0564 (19) | |
H19A | 0.4008 | 0.2072 | 0.2123 | 0.085* | |
H19B | 0.6275 | 0.2535 | 0.1969 | 0.085* | |
H19C | 0.4327 | 0.3425 | 0.1976 | 0.085* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Pd1 | 0.02745 (18) | 0.02875 (17) | 0.03597 (17) | −0.0004 (2) | −0.0021 (2) | 0.00213 (19) |
Cl2 | 0.0515 (11) | 0.0667 (12) | 0.0677 (10) | 0.0150 (10) | 0.0197 (9) | 0.0015 (9) |
Cl1 | 0.0411 (9) | 0.0440 (8) | 0.0529 (8) | 0.0055 (7) | 0.0090 (7) | −0.0006 (7) |
N1 | 0.041 (3) | 0.037 (3) | 0.052 (3) | −0.001 (3) | −0.009 (3) | 0.008 (2) |
N2 | 0.028 (2) | 0.033 (3) | 0.039 (2) | 0.001 (2) | −0.001 (2) | 0.004 (2) |
C1 | 0.038 (3) | 0.037 (3) | 0.037 (3) | −0.011 (3) | −0.005 (3) | 0.000 (2) |
C2 | 0.058 (4) | 0.042 (3) | 0.075 (4) | 0.014 (4) | −0.010 (4) | 0.017 (4) |
C3 | 0.048 (4) | 0.033 (3) | 0.045 (3) | −0.001 (4) | −0.006 (4) | 0.012 (2) |
C4 | 0.074 (6) | 0.049 (4) | 0.064 (4) | 0.004 (4) | 0.012 (4) | 0.002 (3) |
C5 | 0.068 (6) | 0.094 (7) | 0.088 (6) | 0.018 (6) | 0.021 (5) | 0.027 (6) |
C6 | 0.083 (8) | 0.073 (6) | 0.104 (7) | −0.016 (6) | 0.001 (6) | 0.040 (5) |
C7 | 0.109 (9) | 0.047 (4) | 0.089 (6) | −0.018 (5) | −0.017 (6) | 0.015 (4) |
C8 | 0.082 (5) | 0.051 (4) | 0.049 (3) | 0.004 (5) | −0.011 (4) | −0.002 (3) |
C9 | 0.029 (3) | 0.031 (3) | 0.037 (3) | −0.005 (2) | −0.001 (2) | 0.002 (2) |
C10 | 0.035 (3) | 0.035 (3) | 0.039 (3) | −0.006 (3) | 0.000 (2) | 0.001 (3) |
C11 | 0.040 (4) | 0.050 (4) | 0.047 (3) | −0.008 (4) | −0.004 (3) | −0.001 (3) |
C12 | 0.052 (4) | 0.059 (4) | 0.043 (3) | 0.006 (4) | −0.014 (3) | −0.002 (3) |
C13 | 0.077 (5) | 0.054 (4) | 0.034 (3) | −0.001 (4) | 0.010 (4) | 0.005 (3) |
C14 | 0.053 (4) | 0.057 (4) | 0.052 (3) | −0.015 (4) | 0.008 (4) | 0.012 (3) |
C15 | 0.037 (4) | 0.053 (4) | 0.048 (3) | −0.012 (4) | −0.001 (3) | 0.004 (3) |
C16 | 0.030 (3) | 0.040 (3) | 0.046 (3) | −0.003 (3) | 0.002 (3) | −0.005 (3) |
C17 | 0.034 (3) | 0.048 (3) | 0.053 (3) | 0.011 (3) | 0.004 (2) | 0.003 (3) |
C18 | 0.051 (4) | 0.034 (3) | 0.091 (5) | −0.006 (4) | −0.009 (5) | 0.015 (3) |
C19 | 0.056 (5) | 0.068 (5) | 0.044 (3) | 0.006 (4) | −0.010 (3) | 0.012 (3) |
Pd1—C1 | 1.928 (6) | C8—H8 | 0.93 |
Pd1—C9 | 2.006 (5) | C9—C16 | 1.322 (8) |
Pd1—N2 | 2.099 (4) | C9—C10 | 1.486 (7) |
Pd1—Cl1 | 2.3927 (15) | C10—C15 | 1.379 (8) |
Cl2—C16 | 1.762 (6) | C10—C11 | 1.384 (8) |
N1—C1 | 1.148 (7) | C11—C12 | 1.390 (8) |
N1—C2 | 1.445 (8) | C11—H11 | 0.93 |
N2—C19 | 1.478 (7) | C12—C13 | 1.353 (9) |
N2—C18 | 1.483 (8) | C12—H12 | 0.93 |
N2—C17 | 1.485 (7) | C13—C14 | 1.357 (10) |
C2—C3 | 1.513 (9) | C13—H13 | 0.93 |
C2—H2A | 0.97 | C14—C15 | 1.396 (7) |
C2—H2B | 0.97 | C14—H14 | 0.93 |
C3—C4 | 1.365 (9) | C15—H15 | 0.93 |
C3—C8 | 1.377 (8) | C16—C17 | 1.503 (8) |
C4—C5 | 1.371 (11) | C17—H17A | 0.97 |
C4—H4 | 0.93 | C17—H17B | 0.97 |
C5—C6 | 1.363 (11) | C18—H18A | 0.96 |
C5—H5 | 0.93 | C18—H18B | 0.96 |
C6—C7 | 1.364 (12) | C18—H18C | 0.96 |
C6—H6 | 0.93 | C19—H19A | 0.96 |
C7—C8 | 1.376 (11) | C19—H19B | 0.96 |
C7—H7 | 0.93 | C19—H19C | 0.96 |
C1—Pd1—C9 | 94.0 (2) | C10—C9—Pd1 | 125.7 (4) |
C1—Pd1—N2 | 176.6 (2) | C15—C10—C11 | 117.2 (5) |
C9—Pd1—N2 | 83.7 (2) | C15—C10—C9 | 120.1 (5) |
C1—Pd1—Cl1 | 90.08 (18) | C11—C10—C9 | 122.7 (5) |
C9—Pd1—Cl1 | 175.44 (16) | C10—C11—C12 | 120.6 (6) |
N2—Pd1—Cl1 | 92.31 (12) | C10—C11—H11 | 119.7 |
C1—N1—C2 | 176.5 (6) | C12—C11—H11 | 119.7 |
C19—N2—C18 | 108.6 (5) | C13—C12—C11 | 120.7 (6) |
C19—N2—C17 | 108.6 (5) | C13—C12—H12 | 119.7 |
C18—N2—C17 | 110.1 (5) | C11—C12—H12 | 119.7 |
C19—N2—Pd1 | 113.4 (4) | C12—C13—C14 | 120.6 (6) |
C18—N2—Pd1 | 106.5 (4) | C12—C13—H13 | 119.7 |
C17—N2—Pd1 | 109.7 (3) | C14—C13—H13 | 119.7 |
N1—C1—Pd1 | 173.8 (5) | C13—C14—C15 | 119.0 (7) |
N1—C2—C3 | 111.9 (5) | C13—C14—H14 | 120.5 |
N1—C2—H2A | 109.2 | C15—C14—H14 | 120.5 |
C3—C2—H2A | 109.2 | C10—C15—C14 | 122.0 (7) |
N1—C2—H2B | 109.2 | C10—C15—H15 | 119 |
C3—C2—H2B | 109.2 | C14—C15—H15 | 119 |
H2A—C2—H2B | 107.9 | C9—C16—C17 | 123.6 (5) |
C4—C3—C8 | 119.6 (7) | C9—C16—Cl2 | 124.7 (5) |
C4—C3—C2 | 121.5 (6) | C17—C16—Cl2 | 111.7 (4) |
C8—C3—C2 | 118.9 (7) | N2—C17—C16 | 108.3 (5) |
C3—C4—C5 | 120.6 (7) | N2—C17—H17A | 110 |
C3—C4—H4 | 119.7 | C16—C17—H17A | 110 |
C5—C4—H4 | 119.7 | N2—C17—H17B | 110 |
C6—C5—C4 | 119.4 (9) | C16—C17—H17B | 110 |
C6—C5—H5 | 120.3 | H17A—C17—H17B | 108.4 |
C4—C5—H5 | 120.3 | N2—C18—H18A | 109.5 |
C5—C6—C7 | 120.8 (9) | N2—C18—H18B | 109.5 |
C5—C6—H6 | 119.6 | H18A—C18—H18B | 109.5 |
C7—C6—H6 | 119.6 | N2—C18—H18C | 109.5 |
C6—C7—C8 | 119.7 (8) | H18A—C18—H18C | 109.5 |
C6—C7—H7 | 120.2 | H18B—C18—H18C | 109.5 |
C8—C7—H7 | 120.2 | N2—C19—H19A | 109.5 |
C7—C8—C3 | 119.8 (8) | N2—C19—H19B | 109.5 |
C7—C8—H8 | 120.1 | H19A—C19—H19B | 109.5 |
C3—C8—H8 | 120.1 | N2—C19—H19C | 109.5 |
C16—C9—C10 | 122.9 (5) | H19A—C19—H19C | 109.5 |
C16—C9—Pd1 | 111.4 (4) | H19B—C19—H19C | 109.5 |
C1—Pd1—N2—C19 | −90 (3) | Cl1—Pd1—C9—C16 | 35 (2) |
C9—Pd1—N2—C19 | −136.9 (4) | C1—Pd1—C9—C10 | 10.9 (5) |
Cl1—Pd1—N2—C19 | 45.2 (4) | N2—Pd1—C9—C10 | −171.6 (5) |
C1—Pd1—N2—C18 | 151 (3) | Cl1—Pd1—C9—C10 | −144.0 (18) |
C9—Pd1—N2—C18 | 103.8 (4) | C16—C9—C10—C15 | 61.4 (8) |
Cl1—Pd1—N2—C18 | −74.1 (4) | Pd1—C9—C10—C15 | −119.9 (6) |
C1—Pd1—N2—C17 | 32 (3) | C16—C9—C10—C11 | −117.9 (7) |
C9—Pd1—N2—C17 | −15.3 (4) | Pd1—C9—C10—C11 | 60.8 (8) |
Cl1—Pd1—N2—C17 | 166.8 (3) | C15—C10—C11—C12 | −1.5 (9) |
C2—N1—C1—Pd1 | −56 (14) | C9—C10—C11—C12 | 177.8 (6) |
C9—Pd1—C1—N1 | 142 (5) | C10—C11—C12—C13 | 1.8 (10) |
N2—Pd1—C1—N1 | 95 (6) | C11—C12—C13—C14 | −1.3 (11) |
Cl1—Pd1—C1—N1 | −40 (5) | C12—C13—C14—C15 | 0.6 (11) |
C1—N1—C2—C3 | −42 (11) | C11—C10—C15—C14 | 0.8 (10) |
N1—C2—C3—C4 | −49.3 (9) | C9—C10—C15—C14 | −178.6 (6) |
N1—C2—C3—C8 | 130.8 (6) | C13—C14—C15—C10 | −0.3 (10) |
C8—C3—C4—C5 | 0.3 (11) | C10—C9—C16—C17 | −178.3 (6) |
C2—C3—C4—C5 | −179.6 (7) | Pd1—C9—C16—C17 | 2.9 (7) |
C3—C4—C5—C6 | −1.0 (13) | C10—C9—C16—Cl2 | 0.5 (8) |
C4—C5—C6—C7 | 1.2 (15) | Pd1—C9—C16—Cl2 | −178.3 (3) |
C5—C6—C7—C8 | −0.7 (14) | C19—N2—C17—C16 | 143.6 (5) |
C6—C7—C8—C3 | −0.1 (12) | C18—N2—C17—C16 | −97.6 (6) |
C4—C3—C8—C7 | 0.2 (11) | Pd1—N2—C17—C16 | 19.2 (6) |
C2—C3—C8—C7 | −179.8 (6) | C9—C16—C17—N2 | −15.7 (8) |
C1—Pd1—C9—C16 | −170.3 (4) | Cl2—C16—C17—N2 | 165.4 (4) |
N2—Pd1—C9—C16 | 7.2 (4) |
Cg1 is the centroid of the C10–C15 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C19—H19B···Cl1 | 0.96 | 2.65 | 3.275 (8) | 123 |
C17—H17A···Cl1i | 0.97 | 2.80 | 3.729 (6) | 160 |
C4—H4···Cg1 | 0.93 | 2.76 | 3.622 (8) | 155 |
Symmetry code: (i) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | [Pd(C11H13ClN)Cl(C8H7N)] |
Mr | 453.67 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 290 |
a, b, c (Å) | 6.2529 (7), 11.0931 (10), 27.640 (2) |
V (Å3) | 1917.2 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.25 |
Crystal size (mm) | 0.63 × 0.08 × 0.05 |
Data collection | |
Diffractometer | Enraf–Nonius TurboCAD-4 |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.871, 0.928 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3421, 3358, 2420 |
Rint | 0.019 |
(sin θ/λ)max (Å−1) | 0.702 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.085, 1.03 |
No. of reflections | 3358 |
No. of parameters | 219 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.67, −1.07 |
Absolute structure | Flack (1983), 161 Friedel pairs |
Absolute structure parameter | −0.10 (5) |
Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008), WinGX (Farrugia, 2012).
Cg1 is the centroid of the C10–C15 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C19—H19B···Cl1 | 0.96 | 2.65 | 3.275 (8) | 123 |
C17—H17A···Cl1i | 0.97 | 2.80 | 3.729 (6) | 160 |
C4—H4···Cg1 | 0.93 | 2.76 | 3.622 (8) | 155 |
Symmetry code: (i) x−1, y, z. |
Acknowledgements
We are extremely grateful to the late Professor Antonio Carlos Favero Caires for supplying us with the sample used, and to the CNPq National Council for Technological and Scientific Development for supporting this study.
References
Caires, A. C. F., Mauro, A. E., Moro, A. C., de Oliveira Legendre, A. & Ananias, S. R. (2006). Quim. Nova, 29, 750–754. CrossRef CAS Google Scholar
Enraf–Nonius (1994). CAD-4 EXPRESS. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Mafud, A. C., Oliviera, M. A. R. & Gambardella, M. T. P. (2013). Acta Cryst. E69, m15. CSD CrossRef IUCr Journals Google Scholar
Moro, A. C., Mauro, A. E. & Ananias, S. R. (2004). Eclet. Quim. 29, 57–61. CrossRef CAS Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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The title compound was obtained from the reaction between the dimer [Pd(DMBA)(µX)]2 [where X = Cl, N3, NCO, and DMBA = 7,12-dimethylbenz(a)anthracene] and thiourea, being the product of a cleavage reaction. As a palladium complex it could be of interest with respect to anticancer activity.
In the title compound, Fig. 1, the palladium atom coordinates to two C atoms, a Csp2 and a Csp atom [Pd1—C9 2.006 (5) Å, Pd1—C1 1.928 (6) Å, respectively], the amine N atom [Pd1—N2 2.098 (4) Å] and an atom of chlorine [Pd1—Cl1 2.3929 (2) Å], with a square planar geometry. The distances and angles in the title compound are close to those reported for similar compounds (Moro et al., 2004; Caires et al., 2006; Mafud et al., 2013). In the molecule there is a short C-H···Cl contact and a C-H···π interaction (Table 1).
In the crystal, molecules are linked via C-H···Cl hydrogen bonds (Fig. 2 and Table 1) forming chains along the a axis.