μ-Azido-κ2N1:N1-μ-chlorido-bis­[(2-chloro-3-dimethyl­amino-1-phenyl­prop-1-en-1-yl-κ2C1,N)palladium(II)] chloro­form monosolvate

Mafud, A.C.; Oliviera, M.A.R.; Gambardella, M.T.P.

doi:10.1107/S1600536812047927

metal-organic compounds

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ISSN: 2056-9890

Volume 69| Part 1| January 2013| Page m15

https://doi.org/10.1107/S1600536812047927

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μ-Azido-κ²N¹:N¹-μ-chlorido-bis[(2-chloro-3-dimethylamino-1-phenylprop-1-en-1-yl-κ²C¹,N)palladium(II)] chloroform monosolvate

Ana C. Mafud,^a ^* Milene A. R. Oliviera ^b and Maria T. P. Gambardella ^b

^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

(Received 11 November 2012; accepted 21 November 2012; online 8 December 2012)

In the binuclear title complex, [Pd₂(C₁₁H₁₃ClN)₂Cl(N₃)]·CHCl₃, each Pd^II atom has a slightly distorted square-planar geometry being coordinated by a C and an N atom of the 2-chloro-3-dimethylamino-1-phenylpropyl ligand, a bridging Cl atom and an N atom of a bridging end-on azide group. There is a short intramolecular C—H⋯Cl contact in the complex molecule. In the crystal, the chloroform solvent molecule is linked to the complex via a C—H⋯π interaction.

Related literature

For the crystal structures of similar compounds, see: Moro et al. (2004 ); Caires et al. (2006 ).

Experimental

Crystal data

[Pd₂(C₁₁H₁₃ClN)₂Cl(N₃)]·CHCl₃
M_r = 799
Monoclinic, P 2₁ /c
a = 15.416 (3) Å
b = 11.474 (3) Å
c = 17.094 (4) Å
β = 97.14 (2)°
V = 3000.2 (12) Å³
Z = 4
Mo Kα radiation
μ = 1.76 mm⁻¹
T = 293 K
0.2 × 0.1 × 0.1 mm

Data collection

Enraf–Nonius TurboCAD4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.691, T_max = 0.832
7536 measured reflections
7278 independent reflections
2686 reflections with I > 2σ(I)
R_int = 0.066
3 standard reflections every 120 min intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.063
wR(F²) = 0.170
S = 0.93
7278 reflections
329 parameters
H-atom parameters constrained
Δρ_max = 0.75 e Å⁻³
Δρ_min = −0.60 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1A–C6A ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11A—H11B⋯Cl1	0.96	2.74	3.299 (11)	118
C12—H12⋯Cg1ⁱ	0.98	2.77	3.713 (13)	163
Symmetry code: (i) -x+2, -y, -z+1.

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ); cell refinement: 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 ); software used to prepare material for publication: WinGX (Farrugia, 2012).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812047927/su2528sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812047927/su2528Isup2.hkl

checkCIF report

Comment top

In the title compound, Fig. 1, the palladium atoms have distorted square planar geometry. Each palladium atom is connected to two N atoms. One is an N atom of the end-on bridging azide group [Pd1—N1 2.060 (7) and Pd2—N1 2.054 (8) Å] and the other one is the ligand amine group [Pd1—N4 2.064 (7) and Pd2—N5 2.086 (7) Å]. They are also connected to a C atom [Pd1—C7a 1.979 (9) and Pd2—C7b 1.988 (9) Å] and a bridging Cl atom [Pd1—Cl1 2.454 (3) and Pd2—Cl1 2.457 (3) Å]. These distances and angles are close to those reported for similar compounds (Moro et al., 2004; Caires et al., 2006). There is a short intramolecular C-H···Cl interaction (Table 1) in the complex. In the solid state, the title compound crystallized with one molecule of CHCl₃.

In the crystal, the chloroform molecule is linked to the complex via a C-H···π interaction.

Related literature top

For the crystal structures of similar compounds, see: Moro et al. (2004); Caires et al. (2006).

Experimental top

The title compound was synthesized from the interaction between the dimer [Pd(DMBA)(µX)]₂ (where X = Cl, N₃, NCO) and thiourea, being the product of the cleavage reaction. The reaction was performed by mixing a 1:2 stoichiometric amount of[Pd(DMBA)(µN₃)]₂ and thiourea in chloroform at room temperature with constant stirring during 1 h. After the reaction mixture was left for the solvent to slowly evaporate at room temperature. Large yellow needle-like crystals suitable for X-ray diffraction analysis were obtained.

Structure description top

In the crystal, the chloroform molecule is linked to the complex via a C-H···π interaction.

For the crystal structures of similar compounds, see: Moro et al. (2004); Caires et al. (2006).

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: 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); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top

Fig. 1. A view of the molecular structure of the title compound, with the atom numbering. The displacement ellipsoids are drawn at the 50% probability level.

µ-Azido-κ²N¹:N¹-µ-chlorido-bis[(2-chloro-3- dimethylamino-1-phenylprop-1-en-1-yl-κ²C¹,N)palladium(II)] chloroform monosolvate top

Crystal data top

[Pd₂(C₁₁H₁₃ClN)₂Cl(N₃)]·CHCl₃	F(000) = 1576
M_r = 799	D_x = 1.769 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 15 reflections
a = 15.416 (3) Å	θ = 3.5–10.8°
b = 11.474 (3) Å	µ = 1.76 mm⁻¹
c = 17.094 (4) Å	T = 293 K
β = 97.14 (2)°	Prism, red
V = 3000.2 (12) Å³	0.2 × 0.1 × 0.1 mm
Z = 4

Data collection top

Enraf–Nonius TurboCAD4 diffractometer	2686 reflections with I > 2σ(I)
Radiation source: Enraf–Nonius FR590	R_int = 0.066
Graphite monochromator	θ_max = 28.1°, θ_min = 2.9°
non–profiled ω scans	h = −20→0
Absorption correction: ψ scan (North et al., 1968)	k = 0→15
T_min = 0.691, T_max = 0.832	l = −22→22
7536 measured reflections	3 standard reflections every 120 min
7278 independent reflections	intensity decay: 1%

Refinement top

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.170	H-atom parameters constrained
S = 0.93	w = 1/[σ²(F_o²) + (0.0614P)²] where P = (F_o² + 2F_c²)/3
7278 reflections	(Δ/σ)_max = 0.001
329 parameters	Δρ_max = 0.75 e Å⁻³
0 restraints	Δρ_min = −0.60 e Å⁻³

Crystal data top

[Pd₂(C₁₁H₁₃ClN)₂Cl(N₃)]·CHCl₃	V = 3000.2 (12) Å³
M_r = 799	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.416 (3) Å	µ = 1.76 mm⁻¹
b = 11.474 (3) Å	T = 293 K
c = 17.094 (4) Å	0.2 × 0.1 × 0.1 mm
β = 97.14 (2)°

Data collection top

Enraf–Nonius TurboCAD4 diffractometer	2686 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.066
T_min = 0.691, T_max = 0.832	3 standard reflections every 120 min
7536 measured reflections	intensity decay: 1%
7278 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.063	0 restraints
wR(F²) = 0.170	H-atom parameters constrained
S = 0.93	Δρ_max = 0.75 e Å⁻³
7278 reflections	Δρ_min = −0.60 e Å⁻³
329 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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	0.74282 (5)	−0.05511 (7)	0.64046 (4)	0.0494 (3)
Pd2	0.61088 (5)	0.04133 (7)	0.75721 (4)	0.0477 (3)
Cl1	0.58807 (19)	0.0000 (3)	0.61517 (15)	0.0748 (11)
Cl2	1.00891 (19)	−0.1565 (3)	0.58511 (18)	0.0912 (14)
Cl3	0.5788 (2)	0.2278 (3)	0.98230 (18)	0.0847 (11)
N1	0.7132 (5)	−0.0720 (8)	0.7541 (5)	0.060 (3)
N2	0.7335 (7)	−0.1516 (10)	0.7953 (6)	0.072 (4)
N3	0.7551 (7)	−0.2286 (10)	0.8356 (7)	0.097 (5)
N4	0.7701 (6)	−0.0231 (7)	0.5275 (4)	0.056 (3)
N5	0.5100 (6)	0.1623 (7)	0.7548 (5)	0.056 (3)
C1A	0.9152 (6)	−0.1204 (9)	0.7375 (6)	0.052 (4)
C1B	0.6717 (7)	0.0011 (8)	0.9329 (5)	0.049 (3)
C2A	0.9345 (6)	−0.0278 (10)	0.7880 (6)	0.067 (4)
C2B	0.6278 (8)	−0.0717 (10)	0.9781 (6)	0.073 (5)
C3A	0.9793 (8)	−0.0472 (15)	0.8636 (7)	0.098 (6)
C3B	0.6714 (13)	−0.1406 (12)	1.0365 (7)	0.107 (7)
C4A	1.0045 (9)	−0.1571 (17)	0.8864 (7)	0.100 (7)
C4B	0.7603 (14)	−0.1320 (14)	1.0537 (8)	0.112 (8)
C5A	0.9832 (8)	−0.2477 (13)	0.8361 (9)	0.089 (6)
C5B	0.8043 (9)	−0.0626 (14)	1.0078 (9)	0.100 (6)
C6A	0.9400 (8)	−0.2308 (11)	0.7619 (7)	0.077 (5)
C6B	0.7623 (8)	0.0030 (11)	0.9476 (7)	0.082 (5)
C7A	0.8672 (6)	−0.1010 (8)	0.6573 (5)	0.050 (3)
C7B	0.6233 (6)	0.0737 (8)	0.8724 (5)	0.047 (3)
C8A	0.9010 (7)	−0.1115 (9)	0.5911 (6)	0.058 (4)
C8B	0.5814 (7)	0.1672 (10)	0.8879 (6)	0.061 (4)
C9A	0.8470 (7)	−0.0941 (10)	0.5124 (5)	0.066 (4)
C9B	0.5306 (7)	0.2395 (10)	0.8233 (6)	0.076 (5)
C10A	0.7924 (8)	0.1028 (10)	0.5224 (7)	0.082 (5)
C10B	0.4982 (8)	0.2349 (10)	0.6818 (6)	0.086 (5)
C11A	0.6979 (7)	−0.0499 (11)	0.4648 (6)	0.080 (5)
C11B	0.4299 (7)	0.0972 (10)	0.7599 (7)	0.081 (5)
Cl4	0.8090 (3)	−0.0041 (3)	0.2711 (2)	0.1048 (16)
Cl5	0.7771 (3)	0.2344 (3)	0.3010 (3)	0.131 (2)
Cl6	0.7452 (3)	0.1444 (4)	0.1462 (2)	0.147 (2)
C12	0.8118 (8)	0.1356 (10)	0.2348 (7)	0.082 (5)
H9A1	0.88070	−0.05380	0.47650	0.0800*
H9A2	0.82820	−0.16860	0.48940	0.0800*
H2A	0.91790	0.04730	0.77210	0.0800*
H2B	0.56700	−0.07460	0.96930	0.0880*
H9B1	0.47730	0.26910	0.84080	0.0910*
H3A	0.99170	0.01500	0.89810	0.1180*
H3B	0.64050	−0.19280	1.06410	0.1290*
H9B2	0.56550	0.30510	0.80970	0.0910*
H4A	1.03600	−0.17020	0.93560	0.1200*
H4B	0.78980	−0.17290	1.09580	0.1340*
H5A	0.99830	−0.32300	0.85260	0.1070*
H5B	0.86500	−0.05930	1.01760	0.1200*
H6A	0.92760	−0.29390	0.72820	0.0920*
H6B	0.79440	0.04870	0.91660	0.0980*
H10A	0.80110	0.12150	0.46920	0.1220*
H10B	0.84490	0.11890	0.55700	0.1220*
H10C	0.74540	0.14900	0.53770	0.1220*
H10D	0.47440	0.18770	0.63790	0.1290*
H10E	0.55370	0.26580	0.67200	0.1290*
H10F	0.45880	0.29790	0.68860	0.1290*
H11A	0.71670	−0.03560	0.41420	0.1210*
H11B	0.64860	−0.00120	0.47110	0.1210*
H11C	0.68150	−0.13030	0.46850	0.1210*
H11D	0.38130	0.15010	0.75590	0.1220*
H11E	0.43420	0.05700	0.80940	0.1220*
H11F	0.42130	0.04180	0.71760	0.1220*
H12	0.87190	0.15450	0.22620	0.0990*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pd1	0.0517 (5)	0.0582 (5)	0.0388 (4)	−0.0015 (5)	0.0081 (3)	−0.0009 (4)
Pd2	0.0481 (5)	0.0501 (5)	0.0452 (4)	0.0042 (4)	0.0068 (3)	0.0059 (4)
Cl1	0.0710 (19)	0.097 (2)	0.0568 (16)	0.0006 (17)	0.0095 (14)	0.0031 (15)
Cl2	0.0608 (19)	0.135 (3)	0.082 (2)	0.008 (2)	0.0257 (16)	−0.008 (2)
Cl3	0.096 (2)	0.083 (2)	0.0741 (19)	0.0033 (19)	0.0066 (17)	−0.0234 (18)
N1	0.063 (6)	0.061 (7)	0.055 (5)	0.017 (5)	0.009 (4)	0.008 (5)
N2	0.078 (7)	0.062 (7)	0.078 (8)	−0.001 (6)	0.015 (6)	0.006 (6)
N3	0.099 (9)	0.082 (9)	0.113 (9)	0.000 (7)	0.021 (7)	0.025 (7)
N4	0.072 (6)	0.057 (6)	0.040 (4)	−0.001 (5)	0.011 (4)	0.001 (4)
N5	0.063 (6)	0.052 (6)	0.049 (5)	0.008 (5)	−0.005 (4)	0.011 (4)
C1A	0.054 (6)	0.050 (7)	0.054 (6)	−0.005 (5)	0.012 (5)	0.008 (5)
C1B	0.065 (7)	0.045 (6)	0.038 (5)	−0.004 (5)	0.010 (5)	−0.004 (4)
C2A	0.058 (7)	0.078 (9)	0.060 (7)	0.000 (6)	−0.010 (5)	−0.011 (6)
C2B	0.097 (9)	0.074 (9)	0.049 (6)	−0.004 (7)	0.013 (6)	0.012 (6)
C3A	0.079 (9)	0.139 (13)	0.070 (8)	−0.015 (10)	−0.017 (7)	−0.027 (10)
C3B	0.185 (17)	0.083 (10)	0.055 (8)	0.015 (12)	0.024 (10)	0.025 (7)
C4A	0.087 (10)	0.157 (16)	0.053 (8)	0.023 (11)	−0.003 (7)	0.016 (10)
C4B	0.171 (18)	0.097 (12)	0.056 (9)	0.053 (13)	−0.030 (11)	−0.006 (8)
C5A	0.078 (9)	0.094 (11)	0.095 (10)	−0.001 (8)	0.009 (8)	0.031 (9)
C5B	0.076 (9)	0.128 (13)	0.091 (10)	0.013 (10)	−0.011 (8)	0.013 (10)
C6A	0.072 (8)	0.075 (9)	0.080 (9)	−0.015 (7)	−0.005 (7)	0.014 (7)
C6B	0.077 (9)	0.092 (10)	0.071 (8)	0.000 (7)	−0.014 (7)	0.006 (7)
C7A	0.054 (6)	0.053 (6)	0.044 (5)	0.002 (5)	0.010 (5)	−0.001 (5)
C7B	0.037 (5)	0.049 (7)	0.054 (6)	0.003 (5)	0.003 (4)	0.009 (5)
C8A	0.060 (7)	0.053 (7)	0.065 (7)	−0.008 (6)	0.020 (6)	−0.004 (6)
C8B	0.065 (7)	0.061 (8)	0.055 (6)	−0.008 (6)	0.002 (6)	0.002 (6)
C9A	0.065 (7)	0.089 (9)	0.048 (6)	0.002 (6)	0.018 (6)	−0.010 (6)
C9B	0.072 (8)	0.081 (9)	0.074 (8)	0.010 (7)	0.003 (6)	−0.004 (7)
C10A	0.105 (10)	0.074 (9)	0.068 (8)	0.014 (8)	0.020 (7)	0.011 (7)
C10B	0.109 (10)	0.078 (9)	0.073 (8)	0.044 (8)	0.020 (7)	0.021 (7)
C11A	0.080 (8)	0.108 (10)	0.050 (6)	0.008 (8)	−0.005 (6)	0.004 (7)
C11B	0.049 (7)	0.101 (10)	0.091 (9)	0.011 (7)	0.002 (6)	−0.003 (8)
Cl4	0.135 (3)	0.073 (2)	0.108 (3)	0.008 (2)	0.022 (2)	0.015 (2)
Cl5	0.145 (4)	0.102 (3)	0.144 (4)	0.046 (3)	0.007 (3)	−0.038 (3)
Cl6	0.206 (5)	0.143 (4)	0.087 (3)	0.024 (4)	0.004 (3)	0.021 (3)
C12	0.087 (9)	0.066 (8)	0.097 (9)	0.007 (7)	0.022 (7)	0.011 (7)

Geometric parameters (Å, º) top

Pd1—Cl1	2.454 (3)	C5A—C6A	1.371 (19)
Pd1—N1	2.059 (8)	C5B—C6B	1.37 (2)
Pd1—N4	2.060 (7)	C7A—C8A	1.309 (14)
Pd1—C7A	1.975 (9)	C7B—C8B	1.297 (15)
Pd2—Cl1	2.456 (3)	C8A—C9A	1.505 (14)
Pd2—N1	2.050 (8)	C8B—C9B	1.519 (15)
Pd2—N5	2.081 (9)	C2A—H2A	0.9300
Pd2—C7B	1.990 (9)	C2B—H2B	0.9300
Cl2—C8A	1.757 (11)	C3A—H3A	0.9300
Cl3—C8B	1.762 (11)	C3B—H3B	0.9300
Cl4—C12	1.721 (12)	C4A—H4A	0.9300
Cl5—C12	1.733 (13)	C4B—H4B	0.9300
Cl6—C12	1.724 (13)	C5A—H5A	0.9300
N1—N2	1.172 (14)	C5B—H5B	0.9300
N2—N3	1.144 (16)	C6A—H6A	0.9300
N4—C9A	1.487 (14)	C6B—H6B	0.9300
N4—C10A	1.490 (14)	C9A—H9A1	0.9700
N4—C11A	1.478 (13)	C9A—H9A2	0.9700
N5—C9B	1.471 (14)	C9B—H9B2	0.9700
N5—C11B	1.455 (14)	C9B—H9B1	0.9700
N5—C10B	1.493 (14)	C10A—H10B	0.9600
C1A—C7A	1.491 (13)	C10A—H10A	0.9600
C1A—C6A	1.373 (16)	C10A—H10C	0.9600
C1A—C2A	1.378 (15)	C10B—H10D	0.9600
C1B—C2B	1.372 (15)	C10B—H10E	0.9600
C1B—C6B	1.388 (16)	C10B—H10F	0.9600
C1B—C7B	1.459 (13)	C11A—H11C	0.9600
C2A—C3A	1.405 (16)	C11A—H11A	0.9600
C2B—C3B	1.381 (18)	C11A—H11B	0.9600
C3A—C4A	1.36 (2)	C11B—H11D	0.9600
C3B—C4B	1.37 (3)	C11B—H11E	0.9600
C4A—C5A	1.36 (2)	C11B—H11F	0.9600
C4B—C5B	1.36 (2)	C12—H12	0.9800

Cl1—Pd1—N1	82.3 (2)	C3A—C2A—H2A	120.00
Cl1—Pd1—N4	95.5 (3)	C1B—C2B—H2B	119.00
Cl1—Pd1—C7A	178.2 (3)	C3B—C2B—H2B	119.00
N1—Pd1—N4	175.1 (3)	C2A—C3A—H3A	120.00
N1—Pd1—C7A	99.4 (3)	C4A—C3A—H3A	120.00
N4—Pd1—C7A	82.9 (4)	C2B—C3B—H3B	120.00
Cl1—Pd2—N1	82.4 (3)	C4B—C3B—H3B	120.00
Cl1—Pd2—N5	95.4 (2)	C3A—C4A—H4A	120.00
Cl1—Pd2—C7B	177.3 (3)	C5A—C4A—H4A	120.00
N1—Pd2—N5	176.4 (3)	C3B—C4B—H4B	121.00
N1—Pd2—C7B	99.5 (4)	C5B—C4B—H4B	121.00
N5—Pd2—C7B	82.8 (4)	C4A—C5A—H5A	119.00
Pd1—Cl1—Pd2	81.89 (9)	C6A—C5A—H5A	119.00
Pd1—N1—Pd2	103.1 (4)	C4B—C5B—H5B	119.00
Pd1—N1—N2	124.5 (8)	C6B—C5B—H5B	119.00
Pd2—N1—N2	128.9 (8)	C1A—C6A—H6A	120.00
N1—N2—N3	178.6 (12)	C5A—C6A—H6A	120.00
Pd1—N4—C9A	109.0 (5)	C1B—C6B—H6B	120.00
Pd1—N4—C10A	107.7 (6)	C5B—C6B—H6B	120.00
Pd1—N4—C11A	114.8 (7)	N4—C9A—H9A1	110.00
C9A—N4—C10A	109.0 (9)	N4—C9A—H9A2	110.00
C9A—N4—C11A	107.8 (7)	C8A—C9A—H9A1	110.00
C10A—N4—C11A	108.5 (8)	C8A—C9A—H9A2	110.00
Pd2—N5—C9B	107.4 (6)	H9A1—C9A—H9A2	109.00
Pd2—N5—C10B	113.7 (7)	N5—C9B—H9B1	110.00
Pd2—N5—C11B	107.1 (6)	N5—C9B—H9B2	110.00
C9B—N5—C10B	108.7 (8)	C8B—C9B—H9B1	110.00
C9B—N5—C11B	111.2 (8)	C8B—C9B—H9B2	110.00
C10B—N5—C11B	108.7 (9)	H9B1—C9B—H9B2	109.00
C2A—C1A—C6A	119.4 (10)	N4—C10A—H10A	109.00
C2A—C1A—C7A	120.3 (9)	N4—C10A—H10B	109.00
C6A—C1A—C7A	120.3 (9)	N4—C10A—H10C	109.00
C2B—C1B—C6B	117.6 (10)	H10A—C10A—H10B	110.00
C2B—C1B—C7B	120.2 (10)	H10A—C10A—H10C	109.00
C6B—C1B—C7B	122.3 (9)	H10B—C10A—H10C	109.00
C1A—C2A—C3A	119.8 (11)	N5—C10B—H10D	109.00
C1B—C2B—C3B	121.7 (13)	N5—C10B—H10E	109.00
C2A—C3A—C4A	120.0 (13)	N5—C10B—H10F	109.00
C2B—C3B—C4B	119.9 (14)	H10D—C10B—H10E	110.00
C3A—C4A—C5A	119.2 (12)	H10D—C10B—H10F	109.00
C3B—C4B—C5B	118.5 (14)	H10E—C10B—H10F	110.00
C4A—C5A—C6A	121.8 (14)	N4—C11A—H11A	109.00
C4B—C5B—C6B	122.2 (14)	N4—C11A—H11B	109.00
C1A—C6A—C5A	119.8 (12)	N4—C11A—H11C	109.00
C1B—C6B—C5B	119.9 (11)	H11A—C11A—H11B	109.00
Pd1—C7A—C1A	122.4 (6)	H11A—C11A—H11C	110.00
Pd1—C7A—C8A	112.5 (7)	H11B—C11A—H11C	109.00
C1A—C7A—C8A	125.1 (9)	N5—C11B—H11D	109.00
Pd2—C7B—C1B	125.0 (7)	N5—C11B—H11E	109.00
Pd2—C7B—C8B	111.6 (7)	N5—C11B—H11F	109.00
C1B—C7B—C8B	123.5 (9)	H11D—C11B—H11E	110.00
Cl2—C8A—C7A	124.0 (8)	H11D—C11B—H11F	109.00
Cl2—C8A—C9A	114.2 (7)	H11E—C11B—H11F	110.00
C7A—C8A—C9A	121.7 (10)	Cl4—C12—Cl5	110.5 (7)
Cl3—C8B—C7B	125.6 (8)	Cl4—C12—Cl6	109.4 (7)
Cl3—C8B—C9B	112.5 (8)	Cl5—C12—Cl6	109.7 (7)
C7B—C8B—C9B	121.9 (9)	Cl4—C12—H12	109.00
N4—C9A—C8A	106.4 (7)	Cl5—C12—H12	109.00
N5—C9B—C8B	106.9 (9)	Cl6—C12—H12	109.00
C1A—C2A—H2A	120.00

N1—Pd1—Cl1—Pd2	21.6 (3)	C11B—N5—C9B—C8B	85.9 (10)
N4—Pd1—Cl1—Pd2	−153.9 (2)	C6A—C1A—C2A—C3A	0.1 (15)
Cl1—Pd1—N1—Pd2	−26.6 (3)	C7A—C1A—C2A—C3A	179.6 (9)
Cl1—Pd1—N1—N2	133.7 (9)	C2A—C1A—C6A—C5A	0.3 (17)
C7A—Pd1—N1—Pd2	154.1 (4)	C7A—C1A—C6A—C5A	−179.2 (10)
C7A—Pd1—N1—N2	−45.6 (10)	C2A—C1A—C7A—Pd1	−69.6 (11)
Cl1—Pd1—N4—C9A	−155.7 (6)	C2A—C1A—C7A—C8A	110.2 (12)
Cl1—Pd1—N4—C10A	86.2 (7)	C6A—C1A—C7A—Pd1	110.0 (10)
Cl1—Pd1—N4—C11A	−34.8 (7)	C6A—C1A—C7A—C8A	−70.3 (14)
C7A—Pd1—N4—C9A	23.4 (7)	C6B—C1B—C2B—C3B	0.3 (16)
C7A—Pd1—N4—C10A	−94.7 (7)	C7B—C1B—C2B—C3B	−179.2 (10)
C7A—Pd1—N4—C11A	144.4 (8)	C2B—C1B—C6B—C5B	−2.8 (17)
N1—Pd1—C7A—C1A	−7.9 (8)	C7B—C1B—C6B—C5B	176.7 (11)
N1—Pd1—C7A—C8A	172.3 (7)	C2B—C1B—C7B—Pd2	−103.3 (10)
N4—Pd1—C7A—C1A	167.7 (8)	C2B—C1B—C7B—C8B	75.4 (13)
N4—Pd1—C7A—C8A	−12.1 (7)	C6B—C1B—C7B—Pd2	77.3 (12)
N1—Pd2—Cl1—Pd1	−21.7 (3)	C6B—C1B—C7B—C8B	−104.1 (13)
N5—Pd2—Cl1—Pd1	155.4 (2)	C1A—C2A—C3A—C4A	0.8 (17)
Cl1—Pd2—N1—Pd1	26.6 (3)	C1B—C2B—C3B—C4B	4.0 (19)
Cl1—Pd2—N1—N2	−132.5 (10)	C2A—C3A—C4A—C5A	−2.1 (19)
C7B—Pd2—N1—Pd1	−155.4 (4)	C2B—C3B—C4B—C5B	−6 (2)
C7B—Pd2—N1—N2	45.5 (11)	C3A—C4A—C5A—C6A	3 (2)
Cl1—Pd2—N5—C9B	−155.6 (6)	C3B—C4B—C5B—C6B	3 (2)
Cl1—Pd2—N5—C10B	−35.3 (7)	C4A—C5A—C6A—C1A	−1.6 (19)
Cl1—Pd2—N5—C11B	84.8 (7)	C4B—C5B—C6B—C1B	1 (2)
C7B—Pd2—N5—C9B	26.5 (7)	Pd1—C7A—C8A—Cl2	−177.5 (6)
C7B—Pd2—N5—C10B	146.8 (7)	Pd1—C7A—C8A—C9A	−2.2 (13)
C7B—Pd2—N5—C11B	−93.1 (7)	C1A—C7A—C8A—Cl2	2.7 (15)
N1—Pd2—C7B—C1B	−18.8 (9)	C1A—C7A—C8A—C9A	178.0 (9)
N1—Pd2—C7B—C8B	162.4 (8)	Pd2—C7B—C8B—Cl3	−178.0 (6)
N5—Pd2—C7B—C1B	164.0 (9)	Pd2—C7B—C8B—C9B	−0.2 (13)
N5—Pd2—C7B—C8B	−14.8 (8)	C1B—C7B—C8B—Cl3	3.2 (16)
Pd1—N4—C9A—C8A	−28.3 (9)	C1B—C7B—C8B—C9B	−179.1 (10)
C10A—N4—C9A—C8A	88.9 (9)	Cl2—C8A—C9A—N4	−162.9 (7)
C11A—N4—C9A—C8A	−153.5 (8)	C7A—C8A—C9A—N4	21.4 (14)
Pd2—N5—C9B—C8B	−31.1 (9)	Cl3—C8B—C9B—N5	−159.5 (7)
C10B—N5—C9B—C8B	−154.5 (9)	C7B—C8B—C9B—N5	22.5 (14)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1A–C6A ring.

D—H···A	D—H	H···A	D···A	D—H···A
C11A—H11B···Cl1	0.96	2.74	3.299 (11)	118
C12—H12···Cg1ⁱ	0.98	2.77	3.713 (13)	163

Symmetry code: (i) −x+2, −y, −z+1.

Experimental details

Crystal data
Chemical formula	[Pd₂(C₁₁H₁₃ClN)₂Cl(N₃)]·CHCl₃
M_r	799
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	15.416 (3), 11.474 (3), 17.094 (4)
β (°)	97.14 (2)
V (Å³)	3000.2 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.76
Crystal size (mm)	0.2 × 0.1 × 0.1

Data collection
Diffractometer	Enraf–Nonius TurboCAD4
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.691, 0.832
No. of measured, independent and observed [I > 2σ(I)] reflections	7536, 7278, 2686
R_int	0.066
(sin θ/λ)_max (Å⁻¹)	0.662

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.170, 0.93
No. of reflections	7278
No. of parameters	329
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.75, −0.60

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), WinGX (Farrugia, 2012).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1A–C6A ring.

D—H···A	D—H	H···A	D···A	D—H···A
C11A—H11B···Cl1	0.96	2.74	3.299 (11)	118
C12—H12···Cg1ⁱ	0.98	2.77	3.713 (13)	163

Symmetry code: (i) −x+2, −y, −z+1.

Acknowledgements

We are extremely grateful to the late Professor Antonio Carlos Favero Caires for suppling 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). Quím. 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
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Moro, A. C., Mauro, A. E. & Ananias, S. R. (2004). Eclet. Quím. 29, 57–61. 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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