cis-Dichloridobis(2-isocyano­phenyl 4-meth­oxy­benzoate)palladium(II) chloro­form monosolvate

Tskhovrebov, A.; Haukka, M.

doi:10.1107/S1600536812045801

Volume 68
Part 12
Pages m1476-m1477
December 2012

Received 25 September 2012
Accepted 6 November 2012
Online 14 November 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.004 Å
R = 0.037
wR = 0.067
Data-to-parameter ratio = 22.6
Details

cis-Dichloridobis(2-isocyanophenyl 4-methoxybenzoate)palladium(II) chloroform monosolvate

Alexander Tskhovrebov ^a and Matti Haukka ^b ^*

^aDepartment of Chemistry, Saint-Petersburg State University, Universitetsky Pr. 26, 198504 Stary Petergof, Russian Federation, and ^bUniversity of Jyväskylä, Department of Chemistry, PO Box 35, 40014 University of Jyväskylä, Finland
Correspondence e-mail: matti.o.haukka@jyu.fi

In the title compound, [PdCl₂(C₁₅H₁₁NO₃)₂]·CHCl₃, the Pd^II atom adopts a slightly distorted square-planar coordination geometry composed of two Cl atoms in cis positions and two C atoms from isocyanophenyl ligands. The molecular conformation is stabilized by [pi] - [pi] stacking interactions [shortest centroid-centroid distance = 3.600 (1) Å] between substituted benzene rings of different ligands. The crystal packing is characterized by C-HO and C-HCl interactions involving the chloroform solvent molecules.

Related literature

For further information on acyclic diaminocarbenes, see: Slaughter (2012); Boyarskiy et al. (2012). For background to the Passerini reaction, see: Banfi & Riva (2005). For novel metal-mediated coupling as a route to cyclic carbenes and aminocarbene complexes, see: Luzyanin et al. (2009a,b); Tskhovrebov et al. (2011); Chay et al. (2012). For related structures, see: Davies et al. (1996); Bertani et al. (1991); Bonati & Minghetti (1970); Luzyanin et al. (2009a,b); Michelin et al. (1988a,b); Rourke (2007). For bond lengths in coordination complexes, see: Orpen et al. (1989).

Experimental

Crystal data

[PdCl₂(C₁₅H₁₁NO₃)₂]·CHCl₃
M_r = 803.16
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.4457 (1) Å
b = 12.1352 (4) Å
c = 36.1109 (11) Å
V = 3262.80 (15) Å³
Z = 4
Mo K radiation
= 1.02 mm^-1
T = 100 K
0.35 × 0.23 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)T_min = 0.717, T_max = 0.903
24908 measured reflections
9228 independent reflections
7397 reflections with I > 2(I)
R_int = 0.046

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.067
S = 1.01
9228 reflections
408 parameters
H-atom parameters constrained
_max = 0.61 e Å^-3
_min = -0.79 e Å^-3
Absolute structure: Flack (1983), 3936 Friedel pairs
Flack parameter: -0.011 (17)

Table 1
Selected bond lengths (Å)

Pd1-C16	1.935 (3)
Pd1-C1	1.947 (3)
Pd1-Cl2	2.2979 (7)
Pd1-Cl1	2.2994 (7)

Table 2
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C4-H4O2ⁱ	0.95	2.53	3.193 (4)	127
C6-H6O6ⁱⁱ	0.95	2.53	3.433 (4)	158
C19-H19O5ⁱⁱⁱ	0.95	2.37	3.182 (3)	143
C20-H20Cl1^iv	0.95	2.80	3.622 (3)	145
C31-H31Cl1^v	1.00	2.77	3.607 (3)	141
C31-H31Cl2^v	1.00	2.67	3.513 (3)	142
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+2]$ ; (iv) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+2]$ ; (v) x-1, y+1, z.

Data collection: COLLECT (Nonius, 1997); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2009); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZQ2184 ).

Acknowledgements

This work was supported by the Russian Fund for Basic Research (grant 12-03-00076).

References

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metal-organic compounds