metal-organic compounds
Dichlorido{N-[(5-methylthiophen-2-yl)methylidene]-2-(pyridin-2-yl)ethanamine-κ2N,N′}palladium(II)
aChemistry Department, University of the Western Cape, Private Bag X17, Bellville 7535, South Africa
*Correspondence e-mail: monani@uwc.ac.za
In the title compound, [PdCl2(C13H14N2S)], the PdII ion is coordinated by two N atoms of the chelating bidentate ligand and two chloride anions, giving rise to a distorted square-planar geometry. The methyl-substituted thiophene arm and the pyridine ring are connected to the metal cation through N atoms to form a six-membered chelate ring with a boat conformation, making the complex stable.
Related literature
For the synthesis of imino-pyridyl ligands and their transition metal-based complexes, see: Onani & Motswainyana (2011); Motswainyana et al. (2011); Bianchini et al. (2010). For related structures, see: Motswainyana et al. (2012); Chen et al. (2007). For applications of these complexes, see: Ardizzoia et al. (2009); Tianpengfei et al. (2011).
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2006); cell SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97.
Supporting information
https://doi.org/10.1107/S1600536812049240/bh2466sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812049240/bh2466Isup2.hkl
To a suspension of PdCl2(cod) (0.0970 g, 0.34 mmol) in CH2Cl2 (5 ml) was added a solution of the ligand N-(5-methyl-thiophen-2-ylmethylene)-2-pyridineethanamine (0.0666 g, 0.34 mmol) in CH2Cl2 (10 ml). The yellow solution was stirred at room temperature for 8 h., resulting in the formation of a yellow precipitate. The precipitate was filtered, and recrystallization of the product from CH2Cl2 and an excess of C6H14 solution gave single crystals suitable for X-ray diffraction studies. The product yield was 76%.
All non-H atoms were refined anisotropically. All H atoms were placed in idealized positions and refined with constrained C—H distances of 0.95 (aromatic CH), 0.99 (methylene CH2) or 0.98 Å (methyl CH3). Isotropic displacement parameters for H atoms were calculated as Uiso(H) = 1.2Ueq(carrier C), except in the case of the methyl group, for which Uiso(H) = 1.5Ueq(C13).
The imino-pyridyl ligands coordinate as neutral, bidentate species when they are reacted with labile transition metal precursors to form air stable complexes, which show hemilability due to the weakly coordinating N atoms. The complexes could be investigated in various catalytic applications (Bianchini et al., 2010; Motswainyana et al., 2011; Ardizzoia et al., 2009; Tianpengfei et al., 2011).
In our study of imino-pyridyl Pd(II) complexes which could replace the expensive, air and moisture unstable
for catalytic processes, we synthesized and crystallized the title compound (Fig. 1). The Pd atom is coordinated through the two N atoms of the ligand and two chloride anions, generating a distorted square planar coordination geometry around the Pd centre. The bond angles around the Pd metal atom of Cl2—Pd1—Cl1 [92.34 (2)°] and N2—Pd1—N1 [81.73 (7)°] show significant deviations from 90°, which confirms the distortion in the square planar geometry. The angles agree with those of similar compounds (Onani & Motswainyana, 2011; Motswainyana et al., 2012). The Pd1—C11 bond lengths of 2.3016 (6) Å and Pd1—Cl2 of 2.3027 (6) Å are within the limits of the average Pd—Cl bond distance of 2.298 (15) Å for known palladium complexes (Chen et al., 2007). The Pd—Cl bond distances are rather equal, indicating the absence of a trans-influence in the molecule.For the synthesis of imino-pyridyl ligands and their transition metal-based complexes, see: Onani & Motswainyana (2011); Motswainyana et al. (2011); Bianchini et al. (2010). For related structures, see: Motswainyana et al. (2012); Chen et al. (2007). For applications of these complexes, see: Ardizzoia et al. (2009); Tianpengfei et al. (2011).
Data collection: SAINT [or APEX2?] (Bruker, 2006); cell
SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).Fig. 1. Molecular structure of the title complex showing 50% probability displacement ellipsoids for non-H atoms. |
[PdCl2(C13H14N2S)] | F(000) = 808 |
Mr = 407.62 | Dx = 1.820 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 14701 reflections |
a = 12.0110 (5) Å | θ = 1.7–28.3° |
b = 9.1633 (4) Å | µ = 1.73 mm−1 |
c = 13.6456 (6) Å | T = 173 K |
β = 97.930 (1)° | Needle, yellow |
V = 1487.48 (11) Å3 | 0.15 × 0.07 × 0.04 mm |
Z = 4 |
Bruker Kappa DUO APEXII diffractometer | 3706 independent reflections |
Radiation source: fine-focus sealed tube | 3129 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
0.5° φ scans and ω scans | θmax = 28.3°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1997) | h = −16→16 |
Tmin = 0.781, Tmax = 0.934 | k = −12→12 |
14701 measured reflections | l = −18→18 |
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)] = 0.025 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.056 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0227P)2 + 0.6596P] where P = (Fo2 + 2Fc2)/3 |
3706 reflections | (Δ/σ)max = 0.001 |
173 parameters | Δρmax = 0.39 e Å−3 |
0 restraints | Δρmin = −0.62 e Å−3 |
0 constraints |
[PdCl2(C13H14N2S)] | V = 1487.48 (11) Å3 |
Mr = 407.62 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.0110 (5) Å | µ = 1.73 mm−1 |
b = 9.1633 (4) Å | T = 173 K |
c = 13.6456 (6) Å | 0.15 × 0.07 × 0.04 mm |
β = 97.930 (1)° |
Bruker Kappa DUO APEXII diffractometer | 3706 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1997) | 3129 reflections with I > 2σ(I) |
Tmin = 0.781, Tmax = 0.934 | Rint = 0.038 |
14701 measured reflections |
R[F2 > 2σ(F2)] = 0.025 | 0 restraints |
wR(F2) = 0.056 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.39 e Å−3 |
3706 reflections | Δρmin = −0.62 e Å−3 |
173 parameters |
x | y | z | Uiso*/Ueq | ||
Pd1 | 0.253855 (14) | 0.164855 (19) | 0.101073 (12) | 0.01838 (6) | |
Cl1 | 0.35052 (5) | 0.08399 (7) | 0.24845 (4) | 0.02846 (14) | |
Cl2 | 0.08238 (5) | 0.11869 (7) | 0.15214 (4) | 0.02567 (13) | |
S1 | 0.18709 (5) | 0.48733 (6) | 0.13240 (4) | 0.02374 (13) | |
N1 | 0.39778 (16) | 0.2026 (2) | 0.04460 (14) | 0.0229 (4) | |
N2 | 0.18590 (15) | 0.2349 (2) | −0.03402 (14) | 0.0200 (4) | |
C1 | 0.4789 (2) | 0.2919 (3) | 0.0894 (2) | 0.0276 (5) | |
H1 | 0.4720 | 0.3299 | 0.1531 | 0.033* | |
C2 | 0.5710 (2) | 0.3293 (3) | 0.0452 (2) | 0.0356 (6) | |
H2 | 0.6260 | 0.3947 | 0.0768 | 0.043* | |
C3 | 0.5820 (2) | 0.2704 (4) | −0.0453 (2) | 0.0397 (7) | |
H3 | 0.6455 | 0.2940 | −0.0768 | 0.048* | |
C4 | 0.5005 (2) | 0.1767 (3) | −0.0909 (2) | 0.0346 (6) | |
H4 | 0.5085 | 0.1342 | −0.1530 | 0.042* | |
C5 | 0.4071 (2) | 0.1452 (3) | −0.04537 (18) | 0.0248 (5) | |
C6 | 0.3119 (2) | 0.0495 (3) | −0.08966 (18) | 0.0295 (6) | |
H6A | 0.3029 | −0.0311 | −0.0431 | 0.035* | |
H6B | 0.3316 | 0.0057 | −0.1513 | 0.035* | |
C7 | 0.1988 (2) | 0.1301 (3) | −0.11346 (17) | 0.0260 (5) | |
H7A | 0.1962 | 0.1824 | −0.1772 | 0.031* | |
H7B | 0.1363 | 0.0588 | −0.1196 | 0.031* | |
C8 | 0.15436 (18) | 0.3656 (3) | −0.05905 (17) | 0.0208 (5) | |
H8 | 0.1332 | 0.3829 | −0.1277 | 0.025* | |
C9 | 0.14775 (18) | 0.4873 (3) | 0.00534 (16) | 0.0203 (5) | |
C10 | 0.10937 (19) | 0.6228 (3) | −0.02615 (18) | 0.0240 (5) | |
H10 | 0.0836 | 0.6448 | −0.0935 | 0.029* | |
C11 | 0.11169 (19) | 0.7260 (3) | 0.05032 (18) | 0.0248 (5) | |
H11 | 0.0878 | 0.8244 | 0.0401 | 0.030* | |
C12 | 0.15202 (19) | 0.6694 (3) | 0.14103 (18) | 0.0235 (5) | |
C13 | 0.1685 (2) | 0.7445 (3) | 0.23892 (19) | 0.0337 (6) | |
H13A | 0.1380 | 0.8436 | 0.2315 | 0.051* | |
H13B | 0.2490 | 0.7490 | 0.2638 | 0.051* | |
H13C | 0.1295 | 0.6900 | 0.2858 | 0.051* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Pd1 | 0.02171 (9) | 0.01803 (9) | 0.01521 (9) | 0.00063 (7) | 0.00192 (6) | 0.00031 (7) |
Cl1 | 0.0322 (3) | 0.0323 (3) | 0.0194 (3) | 0.0027 (2) | −0.0018 (2) | 0.0039 (2) |
Cl2 | 0.0246 (3) | 0.0253 (3) | 0.0277 (3) | 0.0007 (2) | 0.0059 (2) | 0.0051 (2) |
S1 | 0.0342 (3) | 0.0184 (3) | 0.0181 (3) | 0.0019 (2) | 0.0018 (2) | 0.0024 (2) |
N1 | 0.0241 (10) | 0.0231 (10) | 0.0212 (10) | 0.0031 (8) | 0.0020 (8) | 0.0018 (8) |
N2 | 0.0226 (9) | 0.0210 (10) | 0.0162 (9) | 0.0002 (8) | 0.0017 (7) | −0.0010 (8) |
C1 | 0.0250 (12) | 0.0270 (13) | 0.0300 (14) | 0.0025 (10) | 0.0011 (10) | 0.0013 (11) |
C2 | 0.0246 (12) | 0.0367 (16) | 0.0445 (17) | 0.0001 (11) | 0.0011 (11) | 0.0089 (13) |
C3 | 0.0240 (13) | 0.0556 (19) | 0.0410 (17) | 0.0075 (13) | 0.0104 (12) | 0.0203 (15) |
C4 | 0.0353 (14) | 0.0474 (17) | 0.0226 (13) | 0.0178 (13) | 0.0094 (11) | 0.0080 (12) |
C5 | 0.0291 (12) | 0.0252 (12) | 0.0203 (12) | 0.0087 (10) | 0.0036 (9) | 0.0031 (10) |
C6 | 0.0392 (14) | 0.0271 (13) | 0.0220 (13) | 0.0062 (11) | 0.0034 (10) | −0.0071 (10) |
C7 | 0.0345 (13) | 0.0254 (13) | 0.0171 (12) | −0.0009 (10) | −0.0005 (10) | −0.0060 (9) |
C8 | 0.0203 (10) | 0.0273 (13) | 0.0150 (11) | −0.0006 (9) | 0.0025 (8) | 0.0022 (9) |
C9 | 0.0204 (11) | 0.0247 (12) | 0.0163 (11) | 0.0007 (9) | 0.0039 (8) | 0.0038 (9) |
C10 | 0.0231 (11) | 0.0264 (12) | 0.0226 (12) | 0.0010 (9) | 0.0033 (9) | 0.0077 (10) |
C11 | 0.0232 (11) | 0.0204 (12) | 0.0318 (14) | 0.0027 (9) | 0.0073 (10) | 0.0045 (10) |
C12 | 0.0251 (11) | 0.0186 (11) | 0.0281 (13) | −0.0014 (9) | 0.0083 (9) | 0.0018 (10) |
C13 | 0.0490 (16) | 0.0222 (13) | 0.0319 (15) | −0.0002 (12) | 0.0123 (12) | −0.0023 (11) |
Pd1—N2 | 2.0152 (18) | C5—C6 | 1.500 (3) |
Pd1—N1 | 2.017 (2) | C6—C7 | 1.541 (3) |
Pd1—Cl1 | 2.3016 (6) | C6—H6A | 0.9900 |
Pd1—Cl2 | 2.3027 (6) | C6—H6B | 0.9900 |
S1—C12 | 1.729 (2) | C7—H7A | 0.9900 |
S1—C9 | 1.733 (2) | C7—H7B | 0.9900 |
N1—C1 | 1.352 (3) | C8—C9 | 1.429 (3) |
N1—C5 | 1.355 (3) | C8—H8 | 0.9500 |
N2—C8 | 1.288 (3) | C9—C10 | 1.373 (3) |
N2—C7 | 1.472 (3) | C10—C11 | 1.406 (3) |
C1—C2 | 1.374 (4) | C10—H10 | 0.9500 |
C1—H1 | 0.9500 | C11—C12 | 1.368 (3) |
C2—C3 | 1.371 (4) | C11—H11 | 0.9500 |
C2—H2 | 0.9500 | C12—C13 | 1.491 (3) |
C3—C4 | 1.384 (4) | C13—H13A | 0.9800 |
C3—H3 | 0.9500 | C13—H13B | 0.9800 |
C4—C5 | 1.385 (4) | C13—H13C | 0.9800 |
C4—H4 | 0.9500 | ||
N2—Pd1—N1 | 81.73 (7) | C5—C6—H6B | 108.8 |
N2—Pd1—Cl1 | 173.54 (6) | C7—C6—H6B | 108.8 |
N1—Pd1—Cl1 | 91.91 (6) | H6A—C6—H6B | 107.7 |
N2—Pd1—Cl2 | 93.96 (5) | N2—C7—C6 | 109.68 (19) |
N1—Pd1—Cl2 | 175.20 (6) | N2—C7—H7A | 109.7 |
Cl1—Pd1—Cl2 | 92.34 (2) | C6—C7—H7A | 109.7 |
C12—S1—C9 | 91.90 (12) | N2—C7—H7B | 109.7 |
C1—N1—C5 | 120.0 (2) | C6—C7—H7B | 109.7 |
C1—N1—Pd1 | 122.21 (17) | H7A—C7—H7B | 108.2 |
C5—N1—Pd1 | 117.53 (16) | N2—C8—C9 | 127.0 (2) |
C8—N2—C7 | 117.9 (2) | N2—C8—H8 | 116.5 |
C8—N2—Pd1 | 127.30 (16) | C9—C8—H8 | 116.5 |
C7—N2—Pd1 | 113.28 (15) | C10—C9—C8 | 123.9 (2) |
N1—C1—C2 | 121.7 (3) | C10—C9—S1 | 110.26 (18) |
N1—C1—H1 | 119.1 | C8—C9—S1 | 125.80 (17) |
C2—C1—H1 | 119.1 | C9—C10—C11 | 113.9 (2) |
C3—C2—C1 | 118.7 (3) | C9—C10—H10 | 123.1 |
C3—C2—H2 | 120.6 | C11—C10—H10 | 123.1 |
C1—C2—H2 | 120.6 | C12—C11—C10 | 112.6 (2) |
C2—C3—C4 | 119.9 (3) | C12—C11—H11 | 123.7 |
C2—C3—H3 | 120.0 | C10—C11—H11 | 123.7 |
C4—C3—H3 | 120.0 | C11—C12—C13 | 128.5 (2) |
C3—C4—C5 | 119.6 (3) | C11—C12—S1 | 111.32 (18) |
C3—C4—H4 | 120.2 | C13—C12—S1 | 120.16 (18) |
C5—C4—H4 | 120.2 | C12—C13—H13A | 109.5 |
N1—C5—C4 | 119.9 (2) | C12—C13—H13B | 109.5 |
N1—C5—C6 | 116.0 (2) | H13A—C13—H13B | 109.5 |
C4—C5—C6 | 124.1 (2) | C12—C13—H13C | 109.5 |
C5—C6—C7 | 114.0 (2) | H13A—C13—H13C | 109.5 |
C5—C6—H6A | 108.8 | H13B—C13—H13C | 109.5 |
C7—C6—H6A | 108.8 | ||
N2—Pd1—N1—C1 | 124.39 (19) | N1—C5—C6—C7 | 64.5 (3) |
Cl1—Pd1—N1—C1 | −56.80 (18) | C4—C5—C6—C7 | −115.2 (3) |
N2—Pd1—N1—C5 | −49.93 (17) | C8—N2—C7—C6 | 132.5 (2) |
Cl1—Pd1—N1—C5 | 128.88 (16) | Pd1—N2—C7—C6 | −34.5 (2) |
N1—Pd1—N2—C8 | −94.6 (2) | C5—C6—C7—N2 | −39.7 (3) |
Cl2—Pd1—N2—C8 | 87.59 (19) | C7—N2—C8—C9 | −173.1 (2) |
N1—Pd1—N2—C7 | 71.03 (16) | Pd1—N2—C8—C9 | −8.1 (3) |
Cl2—Pd1—N2—C7 | −106.83 (15) | N2—C8—C9—C10 | −177.5 (2) |
C5—N1—C1—C2 | 1.3 (4) | N2—C8—C9—S1 | 3.0 (4) |
Pd1—N1—C1—C2 | −172.90 (19) | C12—S1—C9—C10 | −0.28 (18) |
N1—C1—C2—C3 | −2.0 (4) | C12—S1—C9—C8 | 179.2 (2) |
C1—C2—C3—C4 | 0.7 (4) | C8—C9—C10—C11 | −179.3 (2) |
C2—C3—C4—C5 | 1.2 (4) | S1—C9—C10—C11 | 0.2 (3) |
C1—N1—C5—C4 | 0.7 (3) | C9—C10—C11—C12 | 0.0 (3) |
Pd1—N1—C5—C4 | 175.19 (18) | C10—C11—C12—C13 | 179.1 (2) |
C1—N1—C5—C6 | −179.0 (2) | C10—C11—C12—S1 | −0.2 (3) |
Pd1—N1—C5—C6 | −4.5 (3) | C9—S1—C12—C11 | 0.27 (19) |
C3—C4—C5—N1 | −2.0 (4) | C9—S1—C12—C13 | −179.1 (2) |
C3—C4—C5—C6 | 177.7 (2) |
Experimental details
Crystal data | |
Chemical formula | [PdCl2(C13H14N2S)] |
Mr | 407.62 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 173 |
a, b, c (Å) | 12.0110 (5), 9.1633 (4), 13.6456 (6) |
β (°) | 97.930 (1) |
V (Å3) | 1487.48 (11) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.73 |
Crystal size (mm) | 0.15 × 0.07 × 0.04 |
Data collection | |
Diffractometer | Bruker Kappa DUO APEXII |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1997) |
Tmin, Tmax | 0.781, 0.934 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14701, 3706, 3129 |
Rint | 0.038 |
(sin θ/λ)max (Å−1) | 0.668 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.025, 0.056, 1.02 |
No. of reflections | 3706 |
No. of parameters | 173 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.39, −0.62 |
Computer programs: SAINT [or APEX2?] (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001).
Acknowledgements
The authors acknowledge financial support from the University of the Western Cape Senate Research, NRF and CSIR.
References
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The imino-pyridyl ligands coordinate as neutral, bidentate species when they are reacted with labile transition metal precursors to form air stable complexes, which show hemilability due to the weakly coordinating N atoms. The complexes could be investigated in various catalytic applications (Bianchini et al., 2010; Motswainyana et al., 2011; Ardizzoia et al., 2009; Tianpengfei et al., 2011).
In our study of imino-pyridyl Pd(II) complexes which could replace the expensive, air and moisture unstable phosphines for catalytic processes, we synthesized and crystallized the title compound (Fig. 1). The Pd atom is coordinated through the two N atoms of the ligand and two chloride anions, generating a distorted square planar coordination geometry around the Pd centre. The bond angles around the Pd metal atom of Cl2—Pd1—Cl1 [92.34 (2)°] and N2—Pd1—N1 [81.73 (7)°] show significant deviations from 90°, which confirms the distortion in the square planar geometry. The angles agree with those of similar compounds (Onani & Motswainyana, 2011; Motswainyana et al., 2012). The Pd1—C11 bond lengths of 2.3016 (6) Å and Pd1—Cl2 of 2.3027 (6) Å are within the limits of the average Pd—Cl bond distance of 2.298 (15) Å for known palladium complexes (Chen et al., 2007). The Pd—Cl bond distances are rather equal, indicating the absence of a trans-influence in the molecule.