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

Tskhovrebov, A.; Haukka, M.

doi:10.1107/S1600536812045801

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Pages m1476-m1477

doi:10.1107/S1600536812045801

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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

(Received 25 September 2012; accepted 6 November 2012; online 14 November 2012)

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 π–π stacking interactions [shortest centroid–centroid distance = 3.600 (1) Å] between substituted benzene rings of different ligands. The crystal packing is characterized by C—H⋯O and C—H⋯Cl 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 Kα radiation
μ = 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 > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.067
S = 1.01
9228 reflections
408 parameters
H-atom parameters constrained
Δρ_max = 0.61 e Å⁻³
Δρ_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—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O2ⁱ	0.95	2.53	3.193 (4)	127
C6—H6⋯O6ⁱⁱ	0.95	2.53	3.433 (4)	158
C19—H19⋯O5ⁱⁱⁱ	0.95	2.37	3.182 (3)	143
C20—H20⋯Cl1^iv	0.95	2.80	3.622 (3)	145
C31—H31⋯Cl1^v	1.00	2.77	3.607 (3)	141
C31—H31⋯Cl2^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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812045801/zq2184sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812045801/zq2184Isup2.hkl

checkCIF report

Comment top

Isocyanides are important organic reagents used in multicomponent reactions such as, e.g., Ugi and Passerini reactions (Banfi & Riva, 2005). Metal complexes of isocyanides could be used as precursors for the generation of coordinated N-heterocyclic carbenes (NHC's) and acyclic diaminocarbenes (ADS's) (Slaughter, 2012). In turn, Pd^II-NHC and Pd^II-ADC systems are particularly interesting since they are used as catalysts in a wide range of cross-coupling reactions (Boyarskiy et al., 2012). Recently, it was observed that the coupling of Pd^II-bound isocyanides and various nucleophiles leads to the formation of cyclic carbenes (Luzyanin et al., 2009b) and ADC complexes (Luzyanin et al., 2009a; Tskhovrebov et al., 2011; Chay et al., 2012), which could not be obtained by the common methods for the generation of metal carbenes. Here we report the structure of a new isocyanide complex that could be used as a starting material for generation of various palladium carbenes.

In the title compound, the isocyanide ligands are mutually in the cis-position (Fig. 1) insofar as the ligated RNC species exhibit higher trans-effect than the chlorides (Davies et al., 1996). The fragments C–N–C–Pd in both complexes are almost linear, viz., the angles N1–C1–Pd1 and N2–C16–Pd1 are 174.2 (2)° and 177.4 (3)°, respectively. The angles C2–N1–C1 and C17–N2–C16 are 174.3 (3)° and 172.0 (3)°, correspondingly. In the isocyanide moieties, the C≡N triple bonds [C1–N1 1.141 (3) Å and C16–N2 1.150 (3) Å] are close to those in some other palladium-isocyanide complexes (Bertani et al., 1991; Bonati & Minghetti, 1970; Luzyanin et al., 2009a,b; Michelin et al., 1988a,b; Orpen et al., 1989; Rourke, 2007). The molecular conformation is stabilized by π-π stacking interactions [shortest centroid-centroid distance = 3.600 (1) Å] between the substituted benzene rings C9–C15 and C17–C22 of different ligands. The crystal packing is characterized by intermolecular C-H···O and C-H···Cl interactions involving the chloroform solvent molecules (Table 1).

Related literature top

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 top

The title compound was synthesized by the addition of 2 equiv of 2-isocyanophenyl-4-methoxybenzoate into a chloroform solution of [PdCl₂(MeCN)₂]. The solid product was dissolved and recrystallized by slow evaporation from a solution of Et₂O/CHCl₃ (1:1, v/v).

Computing details top

Data collection: COLLECT (Nonius, 1997); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.

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

Crystal data top

[PdCl₂(C₁₅H₁₁NO₃)₂]·CHCl₃	F(000) = 1608
M_r = 803.16	D_x = 1.635 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 24908 reflections
a = 7.4457 (1) Å	θ = 3.2–30.0°
b = 12.1352 (4) Å	µ = 1.02 mm⁻¹
c = 36.1109 (11) Å	T = 100 K
V = 3262.80 (15) Å³	Block, colourless
Z = 4	0.35 × 0.23 × 0.10 mm

Data collection top

Nonius KappaCCD diffractometer	9228 independent reflections
Radiation source: fine-focus sealed tube	7397 reflections with I > 2σ(I)
Horizontally mounted graphite crystal monochromator	R_int = 0.046
Detector resolution: 9 pixels mm^-1	θ_max = 30.0°, θ_min = 3.2°
ϕ scans and ω scans with κ offset	h = −10→10
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	k = −17→15
T_min = 0.717, T_max = 0.903	l = −50→41
24908 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)] = 0.037	H-atom parameters constrained
wR(F²) = 0.067	w = 1/[σ²(F_o²) + (0.0262P)²] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.004
9228 reflections	Δρ_max = 0.61 e Å⁻³
408 parameters	Δρ_min = −0.79 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 3936 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.011 (17)

Crystal data top

[PdCl₂(C₁₅H₁₁NO₃)₂]·CHCl₃	V = 3262.80 (15) Å³
M_r = 803.16	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.4457 (1) Å	µ = 1.02 mm⁻¹
b = 12.1352 (4) Å	T = 100 K
c = 36.1109 (11) Å	0.35 × 0.23 × 0.10 mm

Data collection top

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

Refinement top

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

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	U_iso*/U_eq
Pd1	0.70069 (3)	0.468290 (17)	0.888077 (5)	0.01742 (5)
Cl1	0.77179 (10)	0.36814 (6)	0.940105 (18)	0.02588 (17)
Cl2	0.78655 (11)	0.32749 (5)	0.849385 (18)	0.02437 (15)
Cl3	0.19677 (12)	1.19482 (6)	0.947449 (18)	0.02811 (16)
Cl4	0.16546 (10)	1.10483 (7)	0.873361 (19)	0.03021 (18)
Cl5	0.30198 (14)	1.32462 (7)	0.88439 (2)	0.0512 (2)
O1	0.7349 (2)	0.81404 (15)	0.82187 (5)	0.0201 (4)
O2	0.5584 (2)	0.96590 (18)	0.81736 (5)	0.0243 (4)
O3	0.8859 (2)	0.99125 (16)	0.98090 (5)	0.0236 (5)
O4	0.3493 (2)	0.79408 (15)	0.89629 (5)	0.0176 (4)
O5	0.1775 (3)	0.65489 (16)	0.91802 (5)	0.0243 (5)
O6	0.0757 (3)	0.58547 (17)	0.74567 (5)	0.0231 (5)
N1	0.6421 (3)	0.60184 (19)	0.81643 (6)	0.0197 (5)
N2	0.5755 (3)	0.66170 (19)	0.93709 (6)	0.0181 (5)
C1	0.6542 (3)	0.5533 (2)	0.84336 (8)	0.0202 (6)
C2	0.6443 (3)	0.6656 (2)	0.78406 (7)	0.0181 (6)
C3	0.6047 (4)	0.6183 (3)	0.75010 (7)	0.0213 (6)
H3	0.5760	0.5422	0.7484	0.026*
C4	0.6076 (4)	0.6834 (3)	0.71872 (8)	0.0242 (7)
H4	0.5802	0.6522	0.6953	0.029*
C5	0.6502 (4)	0.7939 (3)	0.72142 (8)	0.0246 (7)
H5	0.6505	0.8383	0.6997	0.030*
C6	0.6925 (4)	0.8410 (2)	0.75529 (7)	0.0220 (6)
H6	0.7245	0.9166	0.7567	0.026*
C7	0.6877 (4)	0.7772 (2)	0.78685 (7)	0.0175 (6)
C8	0.6627 (4)	0.9124 (2)	0.83496 (7)	0.0175 (6)
C9	0.7281 (3)	0.9349 (2)	0.87254 (7)	0.0158 (6)
C10	0.6814 (3)	1.0340 (2)	0.88931 (7)	0.0187 (5)
H10	0.6137	1.0867	0.8758	0.022*
C11	0.7323 (3)	1.0570 (2)	0.92547 (7)	0.0186 (6)
H11	0.7003	1.1252	0.9366	0.022*
C12	0.8307 (3)	0.9794 (2)	0.94535 (7)	0.0185 (6)
C13	0.8259 (4)	1.0869 (2)	1.00095 (7)	0.0293 (7)
H13A	0.8686	1.1536	0.9884	0.044*
H13B	0.8739	1.0847	1.0262	0.044*
H13C	0.6944	1.0875	1.0019	0.044*
C14	0.8794 (3)	0.8798 (2)	0.92857 (7)	0.0176 (6)
H14	0.9465	0.8267	0.9421	0.021*
C15	0.8303 (3)	0.8586 (2)	0.89253 (7)	0.0173 (6)
H15	0.8662	0.7916	0.8811	0.021*
C16	0.6242 (4)	0.5885 (2)	0.91953 (7)	0.0194 (6)
C17	0.5048 (4)	0.7558 (2)	0.95387 (7)	0.0165 (6)
C18	0.5512 (3)	0.7851 (2)	0.98970 (7)	0.0176 (6)
H18	0.6306	0.7403	1.0038	0.021*
C19	0.4803 (3)	0.8805 (2)	1.00472 (7)	0.0173 (6)
H19	0.5105	0.9015	1.0293	0.021*
C20	0.3652 (3)	0.9456 (2)	0.98394 (7)	0.0176 (6)
H20	0.3170	1.0110	0.9944	0.021*
C21	0.3197 (4)	0.9165 (2)	0.94812 (7)	0.0171 (6)
H21	0.2407	0.9617	0.9341	0.021*
C22	0.3893 (3)	0.8223 (2)	0.93303 (7)	0.0152 (6)
C23	0.2352 (3)	0.7055 (2)	0.89214 (8)	0.0182 (6)
C24	0.1980 (4)	0.6801 (2)	0.85274 (7)	0.0153 (5)
C25	0.1211 (4)	0.5787 (2)	0.84476 (7)	0.0198 (6)
H25	0.0940	0.5293	0.8644	0.024*
C26	0.0834 (3)	0.5485 (2)	0.80881 (7)	0.0203 (6)
H26	0.0349	0.4778	0.8035	0.024*
C27	0.1174 (3)	0.6232 (2)	0.78018 (7)	0.0185 (6)
C28	0.1047 (4)	0.6582 (3)	0.71486 (7)	0.0269 (7)
H28A	0.0354	0.7260	0.7185	0.040*
H28B	0.0658	0.6221	0.6920	0.040*
H28C	0.2327	0.6763	0.7131	0.040*
C29	0.1902 (4)	0.7258 (2)	0.78777 (7)	0.0185 (6)
H29	0.2117	0.7765	0.7682	0.022*
C30	0.2316 (3)	0.7546 (2)	0.82398 (7)	0.0182 (6)
H30	0.2825	0.8247	0.8292	0.022*
C31	0.1513 (4)	1.2255 (2)	0.90068 (7)	0.0237 (7)
H31	0.0267	1.2557	0.8988	0.028*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pd1	0.02268 (10)	0.01504 (10)	0.01454 (9)	0.00299 (10)	0.00058 (9)	−0.00068 (9)
Cl1	0.0409 (4)	0.0209 (4)	0.0159 (3)	0.0074 (3)	−0.0020 (3)	−0.0008 (3)
Cl2	0.0353 (4)	0.0195 (3)	0.0184 (3)	0.0051 (4)	0.0003 (3)	−0.0039 (3)
Cl3	0.0448 (4)	0.0220 (4)	0.0175 (3)	0.0023 (4)	−0.0028 (4)	0.0009 (3)
Cl4	0.0401 (4)	0.0340 (4)	0.0165 (3)	0.0044 (4)	−0.0049 (3)	−0.0018 (3)
Cl5	0.0628 (5)	0.0512 (6)	0.0397 (5)	−0.0301 (5)	−0.0031 (6)	0.0165 (4)
O1	0.0291 (11)	0.0193 (10)	0.0119 (9)	0.0024 (9)	−0.0041 (8)	−0.0030 (8)
O2	0.0310 (11)	0.0232 (11)	0.0186 (11)	0.0062 (11)	−0.0058 (8)	0.0005 (10)
O3	0.0283 (10)	0.0287 (13)	0.0139 (10)	0.0011 (9)	−0.0028 (8)	−0.0068 (9)
O4	0.0247 (10)	0.0177 (10)	0.0104 (10)	−0.0043 (8)	−0.0010 (7)	0.0006 (7)
O5	0.0324 (11)	0.0296 (12)	0.0109 (9)	−0.0083 (10)	0.0024 (9)	−0.0012 (8)
O6	0.0312 (11)	0.0284 (12)	0.0097 (10)	−0.0021 (10)	−0.0025 (8)	−0.0009 (9)
N1	0.0214 (12)	0.0170 (13)	0.0207 (13)	0.0035 (10)	0.0028 (10)	0.0013 (10)
N2	0.0240 (12)	0.0146 (13)	0.0157 (12)	0.0036 (10)	0.0030 (10)	0.0016 (10)
C1	0.0197 (14)	0.0167 (16)	0.0240 (15)	0.0023 (11)	0.0033 (11)	−0.0053 (12)
C2	0.0170 (13)	0.0228 (16)	0.0145 (14)	0.0005 (12)	0.0000 (11)	0.0000 (12)
C3	0.0226 (14)	0.0219 (16)	0.0194 (15)	−0.0021 (13)	0.0001 (12)	−0.0042 (13)
C4	0.0263 (15)	0.0324 (19)	0.0138 (15)	−0.0011 (14)	0.0004 (12)	−0.0041 (13)
C5	0.0286 (16)	0.0288 (17)	0.0165 (15)	−0.0035 (14)	0.0008 (12)	0.0008 (13)
C6	0.0283 (14)	0.0202 (15)	0.0176 (14)	−0.0023 (15)	0.0017 (14)	−0.0017 (11)
C7	0.0188 (13)	0.0208 (14)	0.0128 (12)	0.0011 (13)	−0.0010 (12)	−0.0037 (11)
C8	0.0210 (15)	0.0163 (14)	0.0150 (13)	−0.0017 (12)	0.0016 (11)	0.0010 (11)
C9	0.0185 (13)	0.0153 (13)	0.0137 (12)	−0.0027 (11)	0.0008 (11)	−0.0002 (10)
C10	0.0196 (12)	0.0157 (12)	0.0207 (13)	0.0019 (13)	−0.0011 (13)	0.0053 (13)
C11	0.0232 (14)	0.0135 (14)	0.0190 (13)	−0.0018 (11)	0.0029 (11)	−0.0015 (10)
C12	0.0182 (13)	0.0235 (15)	0.0138 (13)	−0.0040 (13)	−0.0001 (10)	−0.0022 (12)
C13	0.0363 (18)	0.0322 (18)	0.0192 (15)	−0.0030 (16)	0.0014 (14)	−0.0105 (13)
C14	0.0184 (13)	0.0176 (15)	0.0169 (14)	0.0011 (12)	−0.0009 (11)	0.0029 (12)
C15	0.0167 (13)	0.0175 (14)	0.0177 (14)	−0.0002 (11)	0.0003 (11)	−0.0001 (11)
C16	0.0210 (14)	0.0214 (16)	0.0158 (14)	0.0002 (13)	0.0001 (11)	0.0043 (12)
C17	0.0188 (13)	0.0155 (14)	0.0152 (14)	0.0003 (12)	0.0039 (11)	0.0017 (12)
C18	0.0159 (13)	0.0190 (15)	0.0180 (15)	0.0010 (12)	0.0002 (11)	0.0040 (12)
C19	0.0202 (14)	0.0214 (16)	0.0103 (13)	−0.0052 (13)	0.0006 (11)	−0.0004 (12)
C20	0.0220 (13)	0.0147 (15)	0.0160 (13)	0.0004 (11)	0.0026 (11)	−0.0011 (11)
C21	0.0196 (13)	0.0166 (14)	0.0153 (13)	0.0003 (12)	0.0002 (11)	0.0005 (11)
C22	0.0204 (13)	0.0166 (15)	0.0087 (13)	−0.0034 (12)	0.0002 (10)	0.0009 (11)
C23	0.0189 (13)	0.0194 (14)	0.0162 (14)	0.0025 (11)	0.0020 (11)	0.0006 (12)
C24	0.0158 (12)	0.0183 (13)	0.0118 (12)	−0.0001 (13)	−0.0002 (12)	0.0015 (10)
C25	0.0218 (14)	0.0222 (16)	0.0154 (14)	−0.0002 (12)	0.0018 (11)	0.0032 (12)
C26	0.0214 (13)	0.0196 (17)	0.0198 (14)	−0.0043 (13)	0.0008 (11)	0.0002 (13)
C27	0.0157 (13)	0.0248 (16)	0.0151 (14)	0.0033 (13)	−0.0006 (11)	−0.0011 (12)
C28	0.0300 (16)	0.038 (2)	0.0127 (14)	0.0025 (15)	−0.0032 (13)	0.0035 (13)
C29	0.0196 (13)	0.0231 (15)	0.0128 (12)	0.0003 (14)	−0.0006 (12)	0.0032 (11)
C30	0.0205 (14)	0.0184 (14)	0.0157 (13)	−0.0004 (12)	0.0012 (11)	−0.0024 (11)
C31	0.0267 (15)	0.0252 (17)	0.0192 (15)	0.0005 (13)	−0.0039 (12)	0.0044 (12)

Geometric parameters (Å, º) top

Pd1—C16	1.935 (3)	C10—H10	0.9500
Pd1—C1	1.947 (3)	C11—C12	1.393 (4)
Pd1—Cl2	2.2979 (7)	C11—H11	0.9500
Pd1—Cl1	2.2994 (7)	C12—C14	1.400 (4)
Cl3—C31	1.762 (3)	C13—H13A	0.9800
Cl4—C31	1.768 (3)	C13—H13B	0.9800
Cl5—C31	1.747 (3)	C13—H13C	0.9800
O1—C7	1.387 (3)	C14—C15	1.376 (4)
O1—C8	1.392 (3)	C14—H14	0.9500
O2—C8	1.195 (3)	C15—H15	0.9500
O3—C12	1.356 (3)	C17—C18	1.386 (4)
O3—C13	1.439 (3)	C17—C22	1.400 (4)
O4—C23	1.379 (3)	C18—C19	1.383 (4)
O4—C22	1.402 (3)	C18—H18	0.9500
O5—C23	1.198 (3)	C19—C20	1.386 (4)
O6—C27	1.364 (3)	C19—H19	0.9500
O6—C28	1.437 (3)	C20—C21	1.383 (3)
N1—C1	1.141 (3)	C20—H20	0.9500
N1—C2	1.402 (3)	C21—C22	1.368 (3)
N2—C16	1.150 (3)	C21—H21	0.9500
N2—C17	1.395 (3)	C23—C24	1.482 (3)
C2—C3	1.386 (4)	C24—C25	1.387 (4)
C2—C7	1.396 (4)	C24—C30	1.400 (3)
C3—C4	1.382 (4)	C25—C26	1.378 (3)
C3—H3	0.9500	C25—H25	0.9500
C4—C5	1.381 (4)	C26—C27	1.398 (4)
C4—H4	0.9500	C26—H26	0.9500
C5—C6	1.386 (4)	C27—C29	1.385 (4)
C5—H5	0.9500	C28—H28A	0.9800
C6—C7	1.378 (3)	C28—H28B	0.9800
C6—H6	0.9500	C28—H28C	0.9800
C8—C9	1.467 (3)	C29—C30	1.388 (3)
C9—C10	1.391 (3)	C29—H29	0.9500
C9—C15	1.399 (4)	C30—H30	0.9500
C10—C11	1.388 (3)	C31—H31	1.0000

C16—Pd1—C1	92.00 (12)	C14—C15—C9	120.6 (3)
C16—Pd1—Cl2	178.37 (8)	C14—C15—H15	119.7
C1—Pd1—Cl2	86.52 (8)	C9—C15—H15	119.7
C16—Pd1—Cl1	89.24 (8)	N2—C16—Pd1	177.4 (3)
C1—Pd1—Cl1	176.91 (8)	C18—C17—N2	121.4 (2)
Cl2—Pd1—Cl1	92.28 (3)	C18—C17—C22	120.5 (3)
C7—O1—C8	119.2 (2)	N2—C17—C22	118.1 (2)
C12—O3—C13	117.9 (2)	C19—C18—C17	119.1 (3)
C23—O4—C22	115.11 (19)	C19—C18—H18	120.5
C27—O6—C28	117.8 (2)	C17—C18—H18	120.5
C1—N1—C2	174.3 (3)	C18—C19—C20	120.0 (3)
C16—N2—C17	172.0 (3)	C18—C19—H19	120.0
N1—C1—Pd1	174.2 (2)	C20—C19—H19	120.0
C3—C2—C7	121.0 (3)	C21—C20—C19	120.8 (3)
C3—C2—N1	120.5 (3)	C21—C20—H20	119.6
C7—C2—N1	118.5 (2)	C19—C20—H20	119.6
C4—C3—C2	119.1 (3)	C22—C21—C20	119.5 (2)
C4—C3—H3	120.5	C22—C21—H21	120.2
C2—C3—H3	120.5	C20—C21—H21	120.2
C5—C4—C3	120.1 (3)	C21—C22—C17	120.0 (2)
C5—C4—H4	120.0	C21—C22—O4	120.1 (2)
C3—C4—H4	120.0	C17—C22—O4	119.9 (2)
C4—C5—C6	120.9 (3)	O5—C23—O4	122.4 (3)
C4—C5—H5	119.5	O5—C23—C24	125.2 (2)
C6—C5—H5	119.5	O4—C23—C24	112.4 (2)
C7—C6—C5	119.5 (3)	C25—C24—C30	119.5 (2)
C7—C6—H6	120.2	C25—C24—C23	117.4 (2)
C5—C6—H6	120.2	C30—C24—C23	123.0 (2)
C6—C7—O1	124.5 (2)	C26—C25—C24	121.1 (3)
C6—C7—C2	119.4 (2)	C26—C25—H25	119.5
O1—C7—C2	115.9 (2)	C24—C25—H25	119.5
O2—C8—O1	122.4 (2)	C25—C26—C27	119.1 (3)
O2—C8—C9	127.3 (3)	C25—C26—H26	120.4
O1—C8—C9	110.2 (2)	C27—C26—H26	120.4
C10—C9—C15	118.9 (2)	O6—C27—C29	124.9 (2)
C10—C9—C8	118.7 (2)	O6—C27—C26	114.6 (2)
C15—C9—C8	122.3 (2)	C29—C27—C26	120.5 (2)
C11—C10—C9	121.0 (2)	O6—C28—H28A	109.5
C11—C10—H10	119.5	O6—C28—H28B	109.5
C9—C10—H10	119.5	H28A—C28—H28B	109.5
C10—C11—C12	119.5 (2)	O6—C28—H28C	109.5
C10—C11—H11	120.3	H28A—C28—H28C	109.5
C12—C11—H11	120.3	H28B—C28—H28C	109.5
O3—C12—C11	125.1 (2)	C27—C29—C30	120.0 (2)
O3—C12—C14	115.0 (2)	C27—C29—H29	120.0
C11—C12—C14	119.8 (2)	C30—C29—H29	120.0
O3—C13—H13A	109.5	C29—C30—C24	119.8 (3)
O3—C13—H13B	109.5	C29—C30—H30	120.1
H13A—C13—H13B	109.5	C24—C30—H30	120.1
O3—C13—H13C	109.5	Cl5—C31—Cl3	110.17 (15)
H13A—C13—H13C	109.5	Cl5—C31—Cl4	110.14 (15)
H13B—C13—H13C	109.5	Cl3—C31—Cl4	110.39 (16)
C15—C14—C12	120.1 (3)	Cl5—C31—H31	108.7
C15—C14—H14	119.9	Cl3—C31—H31	108.7
C12—C14—H14	119.9	Cl4—C31—H31	108.7

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O2ⁱ	0.95	2.53	3.193 (4)	127
C6—H6···O6ⁱⁱ	0.95	2.53	3.433 (4)	158
C19—H19···O5ⁱⁱⁱ	0.95	2.37	3.182 (3)	143
C20—H20···Cl1^iv	0.95	2.80	3.622 (3)	145
C31—H31···Cl1^v	1.00	2.77	3.607 (3)	141
C31—H31···Cl2^v	1.00	2.67	3.513 (3)	142

Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x+1, y+1/2, −z+3/2; (iii) x+1/2, −y+3/2, −z+2; (iv) x−1/2, −y+3/2, −z+2; (v) x−1, y+1, z.

Experimental details

Crystal data
Chemical formula	[PdCl₂(C₁₅H₁₁NO₃)₂]·CHCl₃
M_r	803.16
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	7.4457 (1), 12.1352 (4), 36.1109 (11)
V (Å³)	3262.80 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.02
Crystal size (mm)	0.35 × 0.23 × 0.10

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2008)
T_min, T_max	0.717, 0.903
No. of measured, independent and observed [I > 2σ(I)] reflections	24908, 9228, 7397
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.704

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.067, 1.01
No. of reflections	9228
No. of parameters	408
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.61, −0.79
Absolute structure	Flack (1983), 3936 Friedel pairs
Absolute structure parameter	−0.011 (17)

Computer programs: COLLECT (Nonius, 1997), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2009).

Selected bond lengths (Å) top

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O2ⁱ	0.95	2.53	3.193 (4)	127.3
C6—H6···O6ⁱⁱ	0.95	2.53	3.433 (4)	158.0
C19—H19···O5ⁱⁱⁱ	0.95	2.37	3.182 (3)	142.7
C20—H20···Cl1^iv	0.95	2.80	3.622 (3)	145.0
C31—H31···Cl1^v	1.00	2.77	3.607 (3)	141.2
C31—H31···Cl2^v	1.00	2.67	3.513 (3)	141.8

Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x+1, y+1/2, −z+3/2; (iii) x+1/2, −y+3/2, −z+2; (iv) x−1/2, −y+3/2, −z+2; (v) x−1, y+1, z.

Acknowledgements

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

References

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Volume 68| Part 12| December 2012| Pages m1476-m1477

doi:10.1107/S1600536812045801

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

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

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