metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

Chlorido{N-[2-(di­phenylphosphanyl)benz­yl­idene]-2-(2-thienyl)ethanamine-κ2N,P}methylpalladium(II) di­chloro­methane hemisolvate

aUniversity of the Western Cape, Cape Town, Bellville 7535, South Africa, bUniversity of Johannesburg, Auckland Park Kingsway Campus, Johannesburg 2006, South Africa, and cDepartment of Chemistry, Rutgers State University, 73 Warren St, Newark, NJ 07102, USA
*Correspondence e-mail: monani@uwc.ac.za

(Received 26 April 2010; accepted 14 May 2010; online 22 May 2010)

In the title compound, [Pd(CH3)Cl(C25H22NPS)]·0.5C2H2Cl2, the PdII atom is coordinated by the N,P-bidentate ligand, a methyl group and a chloride ion, generating a distorted square-planar PdCClNS coordination geometry, with the N and Cl atoms trans. The thio­phene ring is equally disordered over two orientations and the dichloro­methane solvent mol­ecule is disordered about an inversion centre.

Related literature

For metal-organic compounds with ligands containing both pyridyl and phosphine donor groups and for typical Pd—C, Pd—Cl, Pd—P and Pd—N bond lengths, see: Shaffer & Schmidt (2009[Shaffer, A. R. & Schmidt, J. A. (2009). Organometallica, 28, 2494-2504.]). For the properties of related compounds, see: Tongwa et al. (2009[Tongwa, P., Kinnibrugh, T. L., Kicchaiahgari, G. R., Khrustalev, V. N. & Timofeeva, T. V. (2009). Acta Cryst. C65, o155-o159.]); Jun-Gill et al. (2009[Jun-Gill, K., Sung-Il, O., Dong-Hee, C., Min-Kook, N., Changmoon, P., Young Ju, B., Woo, T. H., Young, J. P., Sang, W. L. & In, T. K. (2009). Bull. Korean Chem. Soc. 30, 1157-1163]).

[Scheme 1]

Experimental

Crystal data
  • [Pd(CH3)Cl(C25H22NPS)]·0.5C2H2Cl2

  • Mr = 598.81

  • Monoclinic, P 21 /n

  • a = 9.9960 (6) Å

  • b = 18.6584 (11) Å

  • c = 13.8167 (8) Å

  • β = 94.517 (1)°

  • V = 2568.9 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 1.09 mm−1

  • T = 173 K

  • 0.16 × 0.15 × 0.14 mm

Data collection
  • Bruker Kappa DUO APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2006[Bruker (2006). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.683, Tmax = 0.746

  • 31867 measured reflections

  • 6376 independent reflections

  • 5600 reflections with I > 2σ(I)

  • Rint = 0.028

Refinement
  • R[F2 > 2σ(F2)] = 0.029

  • wR(F2) = 0.074

  • S = 1.03

  • 6376 reflections

  • 321 parameters

  • 2 restraints

  • H-atom parameters constrained

  • Δρmax = 1.34 e Å−3

  • Δρmin = −1.04 e Å−3

Table 1
Selected bond lengths (Å)

Pd1—C1 2.045 (2)
Pd1—N1 2.158 (2)
Pd1—P1 2.2039 (6)
Pd1—Cl1 2.3628 (6)

Data collection: SMART (Bruker, 2006[Bruker (2006). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

The stucture of the title compound, (I), is shown below. Dimensions are available in the archived CIF. The solvent molecule dichloromethane exhibits high thermal motions and were refined isotropically with temperature factors in the range of 0.101 – 0.122. It is situated close to a centre of inversion. The five-membered ring was disordered and shows two orientations each at 50% s.o.f.: the first ring C7, C8A, C9A, C10A and S1A (ring A) and the second ring C7, C8B, C9B, C10B and S1B (ring B). Ring A and ring B share two common atom sites at C7 and C10A (or C10B). C10A and C10B are on the same site and refined anisotropically with the same temperature factors. The maximum and minimum deviations from the least-squares planes of both rings are 0.086 (4) Å and -0.084 (3) Å for C7 and S1A in ring A, 0.095 (5) Å and -0.090 (3) Å for C7 and S1B in ring B. Angle from the least-square plane of ring A to that of ring B is 36.2 (3)°.

Related literature top

For metal-organic compounds with ligands containing both pyridyl and phosphine donor groups and for typical Pd—C, Pd—Cl, Pd—P and Pd—N bond distances, see: Shaffer & Schmidt (2009). For the properties of related compounds, see: Tongwa et al. (2009); Jun-Gill et al. (2009).

Experimental top

The iminophosphine heterocyclic ligand was prepared via the condensation reaction of 2-(diphenylphosphino)benzaldehyde with 2-thien-2-ylethanamine. The ligand was further refluxed with an equimolar Pd(cod)Cl2 in dichloromethane and gave over 80% yield of a yellow complex. Light-yellow blocks of (I) were grown via slow diffusion of a dichloromethane solution of the complex in hexane a 4

Refinement top

The solvent molecule dichloromethane exhibits high thermal motions and were refined isotropically with temperature factors in the range of 0.101 – 0.122. It is situated on the centre of inversion. Therefore only half of the molecule is in the asymmetric unit and it is modelled as a whole molecule with 50% site occupancy factor (s.o.f.). The 5 member ring was disordered and shows two preferred orientations each at 50% s.o.f.: the first ring C7, C8A, C9A, C10A and S1A (ring A) and the second ring C7, C8B, C9B, C10B and S1B (ring B). Ring A and ring B share two common atom sites at C7 and C10A (or C10B). C10A and C10B are on the same site and refined anisotropically with the same temperature factors. The maximum and minimum deviations from the least-squares planes of both rings are 0.086 (4) Å and -0.084 (3) Å for C7 and S1A in ring A, 0.095 (5) Å and -0.090 (3) Å for C7 and S1B in ring B. Angle from the least-square plane of ring A to that of ring B is 36.2 (3)o. All hydrogen atoms were positioned geometrically with C—H = 0.95 – 0.99 Å and refined as riding on their parent atoms with Uiso (H) = 1.2 - 1.5 Ueq (C).

Structure description top

The following shortfalls have been scrutinized and corrected. 1. ABSTRACT usually does not contain the description of synthesis and crystal preparation, which should be included in _publ_section_exptl_prep section. ABSTRACT should not contain the space group. true

2. _publ_section_exptl_prep section is missing.included

3. _publ_section_exptl_refinement section is missing, in which the treatment of H atoms should be given. rectified

4. _publ_section_figure_captions is missing. Avaialable

5. The solvent molecule in Scheme1 is incorrectly shown. rectified

6. References to published work must be cited in the correct format detailed in Notes for authors. sorted

7. Fig. 2 should show the cell-axis directions (labelled a, b, c) and the cell origin (labelled O). rectified

8. In CIF, the software for data collection is SAINT, and that for cell refinement and data reduction is DENZO-SMN; is it right?

SAINT

Computing details top

Data collection: SMART (Bruker, 2006); cell refinement: 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).

Figures top
[Figure 1] Fig. 1. : The molecular structure of (I) showing 30% displacement ellipsoids (all hydrogen atoms omitted for clarity). The solvent dichloromethane molecule is excluded.
Chlorido{N-[2-(diphenylphosphanyl)benzylidene]-2-(2-thienyl)ethanamine- κ2N,P}methylpalladium(II) dichloromethane hemisolvate top
Crystal data top
[Pd(CH3)Cl(C25H22NPS)]·0.5C2H2Cl2F(000) = 1212
Mr = 598.81Dx = 1.548 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 31867 reflections
a = 9.9960 (6) Åθ = 2.2–28.3°
b = 18.6584 (11) ŵ = 1.09 mm1
c = 13.8167 (8) ÅT = 173 K
β = 94.517 (1)°Needle, light-yellow
V = 2568.9 (3) Å30.16 × 0.15 × 0.14 mm
Z = 4
Data collection top
Bruker Kappa DUO APEXII CCD
diffractometer
6376 independent reflections
Radiation source: fine-focus sealed tube5600 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
0.5° φ scans and ω scansθmax = 28.3°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2006)
h = 1313
Tmin = 0.683, Tmax = 0.746k = 2424
31867 measured reflectionsl = 1818
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.029Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.074H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0301P)2 + 3.2924P]
where P = (Fo2 + 2Fc2)/3
6376 reflections(Δ/σ)max = 0.002
321 parametersΔρmax = 1.34 e Å3
2 restraintsΔρmin = 1.04 e Å3
Crystal data top
[Pd(CH3)Cl(C25H22NPS)]·0.5C2H2Cl2V = 2568.9 (3) Å3
Mr = 598.81Z = 4
Monoclinic, P21/nMo Kα radiation
a = 9.9960 (6) ŵ = 1.09 mm1
b = 18.6584 (11) ÅT = 173 K
c = 13.8167 (8) Å0.16 × 0.15 × 0.14 mm
β = 94.517 (1)°
Data collection top
Bruker Kappa DUO APEXII CCD
diffractometer
6376 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2006)
5600 reflections with I > 2σ(I)
Tmin = 0.683, Tmax = 0.746Rint = 0.028
31867 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0292 restraints
wR(F2) = 0.074H-atom parameters constrained
S = 1.03Δρmax = 1.34 e Å3
6376 reflectionsΔρmin = 1.04 e Å3
321 parameters
Special details top

Experimental. Half sphere of data collected using SAINT strategy (Bruker, 2006). Crystal to detector distance = 50 mm; combination of φ and ω scans of 0.5°, 50 s per °, 2 iterations.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. The solvent molecule dichloromethane exhibits high thermal motions and were refined isotropically with temperature factors in the range of 0.101 C 0.122. It is modelled as a whole molecule with 50% s.o.f. The 5 member ring was disordered and shows two preferred orientations each at 50% s.o.f. All hydrogen atoms were positioned geometrically with C—H = 0.95 C 0.99 A and refined as riding on their parent atoms with Uiso (H) = 1.2 - 1.5 Ueq (C). 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
xyzUiso*/UeqOcc. (<1)
Pd10.636610 (16)0.296906 (8)0.583217 (12)0.02079 (5)
Cl10.51346 (6)0.20048 (3)0.64253 (6)0.03899 (15)
Cl2A1.0260 (4)0.55967 (18)1.0814 (2)0.1066 (9)*0.50
Cl2B0.9080 (4)0.4537 (2)0.9486 (3)0.1223 (11)*0.50
S1A0.3721 (8)0.3256 (4)0.9098 (5)0.0464 (12)0.50
S1B0.3499 (8)0.3404 (4)0.8969 (6)0.0443 (12)0.50
P10.76594 (5)0.38331 (3)0.53464 (4)0.01817 (11)
N10.7551 (2)0.30566 (11)0.72019 (14)0.0289 (4)
C10.5273 (2)0.28695 (14)0.45247 (18)0.0316 (5)
H1A0.57950.26020.40740.047*
H1B0.50620.33470.42590.047*
H1C0.44380.26120.46150.047*
C20.9364 (2)0.34988 (11)0.56117 (16)0.0214 (4)
C30.9725 (2)0.31802 (13)0.65212 (17)0.0268 (5)
C40.8828 (3)0.31090 (14)0.73071 (18)0.0315 (5)
H40.92350.31010.79520.038*
C50.6819 (3)0.30364 (16)0.80910 (18)0.0374 (6)
H5A0.74650.30370.86720.045*
H5B0.62750.25940.81000.045*
C60.5910 (3)0.36912 (17)0.81044 (19)0.0402 (6)
H6A0.64670.41300.80890.048*
H6B0.52840.36890.75130.048*
C70.5115 (3)0.37153 (19)0.8982 (2)0.0455 (7)
C8A0.5216 (8)0.4289 (5)0.9701 (5)0.0549 (18)0.50
H8A0.58390.46740.97080.066*0.50
C8B0.5611 (7)0.3773 (5)0.9925 (5)0.059 (2)0.50
H8B0.65370.38451.01130.070*0.50
C9A0.4239 (8)0.4189 (5)1.0396 (5)0.0569 (19)0.50
H9A0.41640.44921.09420.068*0.50
C9B0.4608 (7)0.3717 (5)1.0608 (4)0.0522 (17)0.50
H9B0.47910.37671.12900.063*0.50
C10A0.3397 (3)0.35877 (19)1.0181 (2)0.0497 (8)0.50
H10A0.27530.34031.05860.060*0.50
C10B0.3397 (3)0.35877 (19)1.0181 (2)0.0497 (8)0.50
H10B0.25890.35951.04990.060*0.50
C111.0318 (2)0.35515 (12)0.49348 (17)0.0263 (5)
H111.00840.37700.43240.032*
C121.1615 (2)0.32884 (14)0.5141 (2)0.0323 (5)
H121.22500.33200.46660.039*
C131.1980 (3)0.29822 (14)0.6033 (2)0.0380 (6)
H131.28630.28030.61750.046*
C141.1042 (3)0.29394 (14)0.6720 (2)0.0358 (6)
H141.13010.27420.73400.043*
C150.7553 (2)0.46247 (11)0.61019 (15)0.0195 (4)
C160.8684 (2)0.49563 (12)0.65553 (16)0.0250 (4)
H160.95520.47700.64730.030*
C170.8542 (3)0.55604 (13)0.71283 (17)0.0306 (5)
H170.93130.57820.74440.037*
C180.7276 (3)0.58398 (13)0.72402 (17)0.0309 (5)
H180.71850.62580.76210.037*
C190.6147 (3)0.55098 (13)0.67984 (17)0.0300 (5)
H190.52810.56990.68830.036*
C200.6280 (2)0.49029 (12)0.62321 (16)0.0249 (4)
H200.55040.46760.59320.030*
C210.7591 (2)0.41830 (11)0.41116 (15)0.0203 (4)
C220.7452 (2)0.49174 (12)0.39294 (16)0.0243 (4)
H220.74240.52440.44550.029*
C230.7355 (3)0.51719 (13)0.29770 (17)0.0312 (5)
H230.72630.56710.28560.037*
C240.7393 (3)0.46996 (15)0.22089 (17)0.0328 (5)
H240.73100.48740.15610.039*
C250.7550 (3)0.39725 (15)0.23840 (17)0.0320 (5)
H250.75930.36500.18550.038*
C260.7644 (2)0.37123 (13)0.33299 (17)0.0268 (5)
H260.77440.32120.34450.032*
C270.9815 (11)0.5338 (5)0.9658 (6)0.101 (3)*0.50
H27A0.91990.57050.93580.121*0.50
H27B1.06320.53420.92970.121*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pd10.01711 (8)0.01957 (8)0.02575 (9)0.00040 (6)0.00207 (6)0.00374 (6)
Cl10.0251 (3)0.0310 (3)0.0611 (4)0.0026 (2)0.0048 (3)0.0200 (3)
S1A0.058 (3)0.0360 (18)0.048 (3)0.0159 (16)0.022 (2)0.0098 (16)
S1B0.0410 (17)0.061 (4)0.0305 (10)0.0139 (19)0.0016 (10)0.0018 (19)
P10.0166 (2)0.0187 (2)0.0192 (2)0.00054 (19)0.00097 (18)0.00085 (19)
N10.0272 (10)0.0343 (11)0.0252 (10)0.0028 (8)0.0030 (8)0.0106 (8)
C10.0256 (11)0.0375 (13)0.0310 (12)0.0099 (10)0.0026 (9)0.0016 (10)
C20.0186 (9)0.0199 (9)0.0257 (10)0.0007 (8)0.0004 (8)0.0008 (8)
C30.0216 (11)0.0281 (11)0.0303 (12)0.0032 (9)0.0013 (9)0.0041 (9)
C40.0290 (12)0.0395 (13)0.0254 (11)0.0054 (10)0.0024 (9)0.0104 (10)
C50.0343 (13)0.0532 (16)0.0253 (12)0.0016 (12)0.0052 (10)0.0140 (11)
C60.0427 (15)0.0537 (17)0.0254 (12)0.0045 (13)0.0099 (11)0.0064 (11)
C70.0359 (14)0.074 (2)0.0269 (13)0.0073 (14)0.0076 (11)0.0028 (13)
C8A0.054 (4)0.072 (5)0.042 (4)0.028 (4)0.018 (3)0.014 (3)
C8B0.032 (3)0.114 (7)0.031 (3)0.017 (4)0.010 (2)0.018 (4)
C9A0.065 (5)0.075 (5)0.034 (3)0.019 (4)0.022 (3)0.016 (3)
C9B0.045 (4)0.089 (6)0.024 (3)0.014 (4)0.010 (2)0.010 (3)
C10A0.0469 (17)0.067 (2)0.0378 (15)0.0110 (15)0.0179 (13)0.0025 (14)
C10B0.0469 (17)0.067 (2)0.0378 (15)0.0110 (15)0.0179 (13)0.0025 (14)
C110.0225 (11)0.0270 (11)0.0295 (11)0.0006 (9)0.0025 (9)0.0015 (9)
C120.0209 (11)0.0333 (12)0.0434 (14)0.0029 (9)0.0072 (10)0.0065 (11)
C130.0214 (11)0.0363 (13)0.0559 (17)0.0080 (10)0.0001 (11)0.0021 (12)
C140.0263 (12)0.0386 (14)0.0413 (14)0.0075 (10)0.0057 (10)0.0095 (11)
C150.0212 (10)0.0198 (9)0.0178 (9)0.0001 (8)0.0030 (7)0.0008 (7)
C160.0220 (10)0.0264 (11)0.0265 (11)0.0005 (8)0.0025 (8)0.0032 (9)
C170.0325 (12)0.0308 (12)0.0285 (12)0.0069 (10)0.0022 (9)0.0070 (9)
C180.0439 (14)0.0256 (11)0.0246 (11)0.0011 (10)0.0107 (10)0.0051 (9)
C190.0307 (12)0.0294 (11)0.0310 (12)0.0074 (10)0.0097 (10)0.0001 (9)
C200.0211 (10)0.0277 (11)0.0261 (11)0.0021 (8)0.0029 (8)0.0011 (9)
C210.0165 (9)0.0240 (10)0.0204 (10)0.0002 (8)0.0012 (7)0.0012 (8)
C220.0262 (11)0.0237 (10)0.0228 (10)0.0029 (8)0.0009 (8)0.0007 (8)
C230.0344 (13)0.0294 (12)0.0295 (12)0.0015 (10)0.0008 (10)0.0079 (9)
C240.0313 (12)0.0450 (14)0.0224 (11)0.0006 (11)0.0041 (9)0.0051 (10)
C250.0310 (12)0.0434 (14)0.0219 (11)0.0052 (11)0.0032 (9)0.0050 (10)
C260.0258 (11)0.0279 (11)0.0267 (11)0.0052 (9)0.0027 (9)0.0022 (9)
Geometric parameters (Å, º) top
Pd1—C12.045 (2)C9A—H9A0.9500
Pd1—N12.158 (2)C9B—H9B0.9500
Pd1—P12.2039 (6)C10A—H10A0.9500
Pd1—Cl12.3628 (6)C11—C121.394 (3)
Cl2A—C271.695 (7)C11—H110.9500
Cl2B—C271.673 (8)C12—C131.381 (4)
S1A—C71.655 (9)C12—H120.9500
S1A—C10A1.673 (9)C13—C141.388 (4)
S1B—C71.715 (9)C13—H130.9500
P1—C151.817 (2)C14—H140.9500
P1—C211.823 (2)C15—C161.394 (3)
P1—C21.825 (2)C15—C201.398 (3)
N1—C41.278 (3)C16—C171.391 (3)
N1—C51.479 (3)C16—H160.9500
C1—H1A0.9800C17—C181.388 (4)
C1—H1B0.9800C17—H170.9500
C1—H1C0.9800C18—C191.384 (4)
C2—C111.391 (3)C18—H180.9500
C2—C31.411 (3)C19—C201.389 (3)
C3—C141.397 (3)C19—H190.9500
C3—C41.467 (3)C20—H200.9500
C4—H40.9500C21—C261.396 (3)
C5—C61.523 (4)C21—C221.398 (3)
C5—H5A0.9900C22—C231.395 (3)
C5—H5B0.9900C22—H220.9500
C6—C71.502 (4)C23—C241.382 (4)
C6—H6A0.9900C23—H230.9500
C6—H6B0.9900C24—C251.385 (4)
C7—C8B1.362 (7)C24—H240.9500
C7—C8A1.459 (8)C25—C261.390 (3)
C8A—C9A1.434 (9)C25—H250.9500
C8A—H8A0.9500C26—H260.9500
C8B—C9B1.434 (8)C27—H27A0.9900
C8B—H8B0.9500C27—H27B0.9900
C9A—C10A1.420 (8)
C1—Pd1—N1178.73 (9)C10A—C9A—H9A123.7
C1—Pd1—P194.76 (7)C8A—C9A—H9A123.7
N1—Pd1—P185.25 (6)C8B—C9B—H9B123.8
C1—Pd1—Cl188.88 (7)C9A—C10A—S1A109.1 (4)
N1—Pd1—Cl191.05 (6)C9A—C10A—H10A125.5
P1—Pd1—Cl1175.36 (2)S1A—C10A—H10A125.5
C7—S1A—C10A96.8 (4)C2—C11—C12120.9 (2)
C15—P1—C21104.30 (10)C2—C11—H11119.6
C15—P1—C2104.99 (10)C12—C11—H11119.6
C21—P1—C2106.03 (10)C13—C12—C11120.3 (2)
C15—P1—Pd1110.94 (7)C13—C12—H12119.9
C21—P1—Pd1124.56 (7)C11—C12—H12119.9
C2—P1—Pd1104.47 (7)C12—C13—C14119.3 (2)
C4—N1—C5117.6 (2)C12—C13—H13120.4
C4—N1—Pd1125.45 (17)C14—C13—H13120.4
C5—N1—Pd1116.96 (16)C13—C14—C3121.6 (2)
Pd1—C1—H1A109.5C13—C14—H14119.2
Pd1—C1—H1B109.5C3—C14—H14119.2
H1A—C1—H1B109.5C16—C15—C20119.4 (2)
Pd1—C1—H1C109.5C16—C15—P1122.46 (16)
H1A—C1—H1C109.5C20—C15—P1118.09 (16)
H1B—C1—H1C109.5C17—C16—C15120.0 (2)
C11—C2—C3119.2 (2)C17—C16—H16120.0
C11—C2—P1121.32 (17)C15—C16—H16120.0
C3—C2—P1119.46 (17)C18—C17—C16120.2 (2)
C14—C3—C2118.7 (2)C18—C17—H17119.9
C14—C3—C4116.5 (2)C16—C17—H17119.9
C2—C3—C4124.7 (2)C19—C18—C17120.2 (2)
N1—C4—C3125.9 (2)C19—C18—H18119.9
N1—C4—H4117.1C17—C18—H18119.9
C3—C4—H4117.1C18—C19—C20120.0 (2)
N1—C5—C6108.9 (2)C18—C19—H19120.0
N1—C5—H5A109.9C20—C19—H19120.0
C6—C5—H5A109.9C19—C20—C15120.2 (2)
N1—C5—H5B109.9C19—C20—H20119.9
C6—C5—H5B109.9C15—C20—H20119.9
H5A—C5—H5B108.3C26—C21—C22119.1 (2)
C7—C6—C5112.8 (2)C26—C21—P1119.85 (17)
C7—C6—H6A109.0C22—C21—P1121.03 (16)
C5—C6—H6A109.0C23—C22—C21120.1 (2)
C7—C6—H6B109.0C23—C22—H22119.9
C5—C6—H6B109.0C21—C22—H22119.9
H6A—C6—H6B107.8C24—C23—C22120.2 (2)
C8B—C7—C8A44.7 (4)C24—C23—H23119.9
C8B—C7—C6126.8 (4)C22—C23—H23119.9
C8A—C7—C6124.0 (4)C23—C24—C25120.0 (2)
C8B—C7—S1A101.2 (4)C23—C24—H24120.0
C8A—C7—S1A109.1 (4)C25—C24—H24120.0
C6—C7—S1A124.5 (4)C24—C25—C26120.3 (2)
C8B—C7—S1B108.0 (4)C24—C25—H25119.8
C8A—C7—S1B105.6 (4)C26—C25—H25119.8
C6—C7—S1B122.7 (4)C25—C26—C21120.2 (2)
S1A—C7—S1B13.1 (3)C25—C26—H26119.9
C9A—C8A—C7110.3 (6)C21—C26—H26119.9
C9A—C8A—H8A124.8Cl2B—C27—Cl2A117.9 (6)
C7—C8A—H8A124.8Cl2B—C27—H27A107.8
C7—C8B—C9B113.8 (5)Cl2A—C27—H27A107.8
C7—C8B—H8B123.1Cl2B—C27—H27B107.8
C9B—C8B—H8B123.1Cl2A—C27—H27B107.8
C10A—C9A—C8A112.7 (6)H27A—C27—H27B107.2
C1—Pd1—P1—C15122.52 (11)S1B—C7—C8A—C9A24.7 (8)
N1—Pd1—P1—C1558.75 (9)C8A—C7—C8B—C9B81.6 (9)
Cl1—Pd1—P1—C1596.0 (3)C6—C7—C8B—C9B174.7 (6)
C1—Pd1—P1—C213.25 (11)S1A—C7—C8B—C9B24.3 (9)
N1—Pd1—P1—C21175.47 (10)S1B—C7—C8B—C9B12.7 (10)
Cl1—Pd1—P1—C21138.3 (3)C7—C8A—C9A—C10A2.9 (10)
C1—Pd1—P1—C2124.85 (11)C8A—C9A—C10A—S1A6.9 (9)
N1—Pd1—P1—C253.87 (9)C7—S1A—C10A—C9A12.1 (6)
Cl1—Pd1—P1—C216.7 (3)C3—C2—C11—C120.6 (3)
C1—Pd1—N1—C446 (4)P1—C2—C11—C12179.39 (18)
P1—Pd1—N1—C444.6 (2)C2—C11—C12—C131.2 (4)
Cl1—Pd1—N1—C4132.6 (2)C11—C12—C13—C140.0 (4)
C1—Pd1—N1—C5133 (4)C12—C13—C14—C31.9 (4)
P1—Pd1—N1—C5136.99 (18)C2—C3—C14—C132.5 (4)
Cl1—Pd1—N1—C545.81 (17)C4—C3—C14—C13179.8 (2)
C15—P1—C2—C11109.01 (19)C21—P1—C15—C1696.92 (19)
C21—P1—C2—C111.0 (2)C2—P1—C15—C1614.4 (2)
Pd1—P1—C2—C11134.17 (17)Pd1—P1—C15—C16126.67 (17)
C15—P1—C2—C370.99 (19)C21—P1—C15—C2083.53 (18)
C21—P1—C2—C3178.95 (18)C2—P1—C15—C20165.18 (17)
Pd1—P1—C2—C345.83 (19)Pd1—P1—C15—C2052.88 (18)
C11—C2—C3—C141.2 (3)C20—C15—C16—C170.3 (3)
P1—C2—C3—C14178.79 (19)P1—C15—C16—C17179.81 (18)
C11—C2—C3—C4178.3 (2)C15—C16—C17—C180.8 (4)
P1—C2—C3—C41.7 (3)C16—C17—C18—C191.3 (4)
C5—N1—C4—C3176.1 (2)C17—C18—C19—C200.8 (4)
Pd1—N1—C4—C35.4 (4)C18—C19—C20—C150.3 (4)
C14—C3—C4—N1154.4 (3)C16—C15—C20—C190.8 (3)
C2—C3—C4—N128.5 (4)P1—C15—C20—C19179.61 (17)
C4—N1—C5—C6116.9 (3)C15—P1—C21—C26179.72 (17)
Pd1—N1—C5—C664.6 (3)C2—P1—C21—C2669.74 (19)
N1—C5—C6—C7179.6 (2)Pd1—P1—C21—C2651.2 (2)
C5—C6—C7—C8B63.5 (7)C15—P1—C21—C221.3 (2)
C5—C6—C7—C8A119.0 (5)C2—P1—C21—C22111.86 (18)
C5—C6—C7—S1A80.4 (4)Pd1—P1—C21—C22127.25 (16)
C5—C6—C7—S1B96.0 (4)C26—C21—C22—C230.6 (3)
C10A—S1A—C7—C8B32.0 (5)P1—C21—C22—C23177.78 (18)
C10A—S1A—C7—C8A13.7 (5)C21—C22—C23—C240.1 (4)
C10A—S1A—C7—C6176.8 (3)C22—C23—C24—C251.1 (4)
C10A—S1A—C7—S1B90 (3)C23—C24—C25—C261.3 (4)
C8B—C7—C8A—C9A75.3 (8)C24—C25—C26—C210.5 (4)
C6—C7—C8A—C9A174.6 (6)C22—C21—C26—C250.5 (3)
S1A—C7—C8A—C9A11.4 (8)P1—C21—C26—C25177.97 (18)

Experimental details

Crystal data
Chemical formula[Pd(CH3)Cl(C25H22NPS)]·0.5C2H2Cl2
Mr598.81
Crystal system, space groupMonoclinic, P21/n
Temperature (K)173
a, b, c (Å)9.9960 (6), 18.6584 (11), 13.8167 (8)
β (°) 94.517 (1)
V3)2568.9 (3)
Z4
Radiation typeMo Kα
µ (mm1)1.09
Crystal size (mm)0.16 × 0.15 × 0.14
Data collection
DiffractometerBruker Kappa DUO APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2006)
Tmin, Tmax0.683, 0.746
No. of measured, independent and
observed [I > 2σ(I)] reflections
31867, 6376, 5600
Rint0.028
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.029, 0.074, 1.03
No. of reflections6376
No. of parameters321
No. of restraints2
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.34, 1.04

Computer programs: SMART (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001).

Selected bond lengths (Å) top
Pd1—C12.045 (2)Pd1—P12.2039 (6)
Pd1—N12.158 (2)Pd1—Cl12.3628 (6)
 

Acknowledgements

We acknowledge the University of the Western Cape and the Ministry of Health of Botswana (WMM) for funding.

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191  CrossRef CAS Google Scholar
First citationBruker (2006). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationJun-Gill, K., Sung-Il, O., Dong-Hee, C., Min-Kook, N., Changmoon, P., Young Ju, B., Woo, T. H., Young, J. P., Sang, W. L. & In, T. K. (2009). Bull. Korean Chem. Soc. 30, 1157–1163  Google Scholar
First citationShaffer, A. R. & Schmidt, J. A. (2009). Organometallica, 28, 2494–2504.  Web of Science CSD CrossRef CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationTongwa, P., Kinnibrugh, T. L., Kicchaiahgari, G. R., Khrustalev, V. N. & Timofeeva, T. V. (2009). Acta Cryst. C65, o155–o159.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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