Dichloridobis[(ferrocenyl­methyl­idene)(furan-2-ylmeth­yl)amine-κN]palladium(II)

Motswainyana, W.M.; Onani, M.O.; Lalancette, R.A.

doi:10.1107/S1600536812009191

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Page m387

doi:10.1107/S1600536812009191

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Dichloridobis[(ferrocenylmethylidene)(furan-2-ylmethyl)amine-κN]palladium(II)

William M. Motswainyana,^a Martin O. Onani ^a and Roger A. Lalancette ^b ^*

^aChemistry Department, University of the Western Cape, Modderdam Road, Private bag X17, Bellville, 7535, South Africa, and ^bCarl A. Olson Memorial Laboratories, Department of Chemistry, Rutgers University, Newark, NJ 07102 USA
^*Correspondence e-mail: rogerlal@andromeda.rutgers.edu

(Received 16 February 2012; accepted 1 March 2012; online 7 March 2012)

The title compound, [Fe₂Pd(C₅H₅)₂(C₁₁H₁₀NO)₂Cl₂], exhibits a square-planar geometry at the Pd^II atom, which is determined by inversion-related chlorine and ferrocenylimine molecules across a center of symmetry. The ferrocenylimine moieties are trans to each other.

Related literature

For the synthesis of ferrocenylimine ligands and their transition metal-based complexes, see: Mu et al. (2007 ); Lu et al. (2007 ); Pou et al. (2007 ); Neuse et al. (1988 ). For related structures, see: Rajput et al. (2004 , 2006 ); Nelana et al. (2008 ). For related applications, see: Stang et al. (1996 ); Pou et al. (2007). For Pd—Cl bond lengths, see: Allen (2002 ). For the preparation of the precursor molecule, see: Salo & Guan (2003 ).

Experimental

Crystal data

[Fe₂Pd(C₅H₅)₂(C₁₁H₁₀NO)₂Cl₂]
M_r = 763.58
Monoclinic, P 2₁ /n
a = 12.2113 (7) Å
b = 7.3439 (5) Å
c = 16.365 (1) Å
β = 100.616 (4)°
V = 1442.44 (16) Å³
Z = 2
Cu Kα radiation
μ = 14.91 mm⁻¹
T = 100 K
0.44 × 0.07 × 0.04 mm

Data collection

Bruker SMART CCD APEXII area-detector diffractometer
Absorption correction: numerical (SADABS; Sheldrick, 2008a ; Parkin et al., 1995 ) T_min = 0.059, T_max = 0.560
12086 measured reflections
2598 independent reflections
1886 reflections with I > 2σ(I)
R_int = 0.088

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.109
S = 1.02
2598 reflections
187 parameters
H-atom parameters constrained
Δρ_max = 0.85 e Å⁻³
Δρ_min = −1.01 e Å⁻³

Data collection: APEX2 (Bruker, 2006 ); cell refinement: SAINT (Bruker, 2005 ); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008b ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, New_Global_Publ_Block, global. DOI: 10.1107/S1600536812009191/pk2391sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812009191/pk2391Isup2.hkl

checkCIF report

Comment top

Ferrocenyl derivatives containing good donor atoms have evoked research interest because their coordination to another metal produces multicentered molecules where the two metals are in close proximity but in different environments. This property may influence the mutual cooperation of the metals in a variety of application processes (Stang et al., 1996; Rajput et al., 2004; Rajput et al., 2006; Neuse et al., 1988; Pou et al., 2007). For instance, some ferrocenyl complexes have displayed promising cytotoxicity profiles (Neuse et al., 1988; Pou et al., 2007). Preference for these complexes is derived from their convenience of preparation, facile modification and handling (Mu et al., 2007; Lu et al., 2007). In an attempt to prepare new bulky bis(ferrocenylimine) palladium^II complexes which could induce apoptosis on tumor cells, the title compound was obtained.

The molecular structure contains one molecule of the Pd^II complex (Fig. 1) across a center of symmetry (one-half of the molecule is the asymmetric unit). All bond lengths and angles are normal and comparable with those reported for similar structures (Rajput et al., 2004; Nelana et al., 2008; Pou et al., 2007). The Pd^II ion has square planar coordination geometry around the metal center coordinated to two ferrocenylimine ligands via the imine nitrogen atoms and the chloride ions. The ferrocenylimine molecules are trans to each other across the center of symmetry. There is no trans influence observed for the chloride ligands: the Pd–Cl bond length is in agreement with known Pd–Cl bond distances for palladium complexes (Allen, 2002).

Related literature top

For the synthesis of ferrocenylimine ligands and their transition metal-based complexes, see: Mu et al. (2007); Lu et al. (2007); Pou et al. (2007); Neuse et al. (1988). For related structures, see: Rajput et al. (2004, 2006); Nelana et al. (2008). For related applications see: Stang et al. (1996); Pou et al. (2007). For Pd—Cl bond distances, see: Allen (2002). For the preparation of the precursor molecule, see: Salo & Guan (2003).

Experimental top

[PdCl₂(cod)] was prepared following literature method (Salo & Guan, 2003). To a suspension of PdCl₂(cod) [0.0394 g, 0.138 mmol] in a mixture of CH₂Cl₂/Et₂O (20 ml) was added a solution of ferrocenyl-2-furylmethyl)imine (0.0801 g, 0.2732 mmol) in CH₂Cl₂ (5 ml). An orange precipitate was observed immediately. The reaction was stirred at room temperature for 12 hrs. The precipitate was filtered off, washed with dry hexane (2 x 5 ml) and dried under vacuum to yield an orange solid. Recrystallization of the product was done from a mixture of CH₂Cl₂:C₆H₁₄ which gave single crystals which were used for the X-ray diffraction studies. The yield of the product was 0.0738 g which translates to 70%.

Structure description top

For the synthesis of ferrocenylimine ligands and their transition metal-based complexes, see: Mu et al. (2007); Lu et al. (2007); Pou et al. (2007); Neuse et al. (1988). For related structures, see: Rajput et al. (2004, 2006); Nelana et al. (2008). For related applications see: Stang et al. (1996); Pou et al. (2007). For Pd—Cl bond distances, see: Allen (2002). For the preparation of the precursor molecule, see: Salo & Guan (2003).

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008b); program(s) used to refine structure: SHELXTL (Sheldrick, 2008b); molecular graphics: SHELXTL (Sheldrick, 2008b); software used to prepare material for publication: SHELXTL (Sheldrick, 2008b).

Figures top

Fig. 1. A view of the molecular structure with displacement ellipsoids drawn at the 30% probability level for non-H atoms.

Dichloridobis[(ferrocenylmethylidene)(furan-2-ylmethyl)amine-κN] palladium(II) top

Crystal data top

[Fe₂Pd(C₅H₅)₂(C₁₁H₁₀NO)₂Cl₂]	F(000) = 768
M_r = 763.58	D_x = 1.758 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2yn	Cell parameters from 5083 reflections
a = 12.2113 (7) Å	θ = 4.2–71.6°
b = 7.3439 (5) Å	µ = 14.91 mm⁻¹
c = 16.365 (1) Å	T = 100 K
β = 100.616 (4)°	Needle, red
V = 1442.44 (16) Å³	0.44 × 0.07 × 0.04 mm
Z = 2

Data collection top

Bruker SMART CCD APEXII area-detector diffractometer	2598 independent reflections
Radiation source: fine-focus sealed tube	1886 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.088
φ and ω scans	θ_max = 71.6°, θ_min = 4.2°
Absorption correction: numerical (SADABS; Sheldrick, 2008a; Parkin et al., 1995)	h = −14→14
T_min = 0.059, T_max = 0.560	k = −7→8
12086 measured reflections	l = −18→19

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.053P)²] where P = (F_o² + 2F_c²)/3
2598 reflections	(Δ/σ)_max < 0.001
187 parameters	Δρ_max = 0.85 e Å⁻³
0 restraints	Δρ_min = −1.01 e Å⁻³

Crystal data top

[Fe₂Pd(C₅H₅)₂(C₁₁H₁₀NO)₂Cl₂]	V = 1442.44 (16) Å³
M_r = 763.58	Z = 2
Monoclinic, P2₁/n	Cu Kα radiation
a = 12.2113 (7) Å	µ = 14.91 mm⁻¹
b = 7.3439 (5) Å	T = 100 K
c = 16.365 (1) Å	0.44 × 0.07 × 0.04 mm
β = 100.616 (4)°

Data collection top

Bruker SMART CCD APEXII area-detector diffractometer	2598 independent reflections
Absorption correction: numerical (SADABS; Sheldrick, 2008a; Parkin et al., 1995)	1886 reflections with I > 2σ(I)
T_min = 0.059, T_max = 0.560	R_int = 0.088
12086 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.109	H-atom parameters constrained
S = 1.02	Δρ_max = 0.85 e Å⁻³
2598 reflections	Δρ_min = −1.01 e Å⁻³
187 parameters

Special details top

Experimental. 'Crystal mounted on a Cryoloop using Paratone-N.'

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	0.5000	0.0000	0.5000	0.01970 (17)
Fe1	0.16463 (7)	0.24226 (12)	0.38773 (5)	0.0222 (2)
Cl1	0.50057 (10)	−0.24917 (19)	0.41448 (8)	0.0259 (3)
O1	0.6314 (3)	0.0915 (7)	0.2825 (3)	0.0447 (12)
N1	0.4827 (3)	0.1692 (6)	0.4011 (3)	0.0216 (10)
C1	0.3939 (4)	0.2003 (7)	0.3462 (3)	0.0237 (12)
H1	0.4004	0.2900	0.3055	0.028*
C2	0.2862 (4)	0.1145 (7)	0.3395 (3)	0.0212 (12)
C3	0.2431 (4)	−0.0047 (8)	0.3950 (3)	0.0221 (11)
H3	0.2866	−0.0615	0.4464	0.026*
C4	0.1275 (4)	−0.0274 (8)	0.3641 (3)	0.0247 (13)
H4	0.0752	−0.1019	0.3907	0.030*
C5	0.0977 (5)	0.0775 (8)	0.2905 (3)	0.0243 (13)
H5	0.0211	0.0886	0.2565	0.029*
C6	0.1943 (4)	0.1658 (8)	0.2740 (3)	0.0243 (12)
H6	0.1985	0.2483	0.2260	0.029*
C7	0.2220 (5)	0.4917 (9)	0.4320 (4)	0.0366 (14)
H7	0.2929	0.5502	0.4233	0.044*
C8	0.2098 (5)	0.3762 (8)	0.4999 (3)	0.0333 (15)
H8	0.2702	0.3391	0.5468	0.040*
C9	0.0967 (5)	0.3196 (8)	0.4873 (4)	0.0327 (14)
H9	0.0629	0.2367	0.5243	0.039*
C10	0.0392 (5)	0.4038 (8)	0.4125 (4)	0.0330 (15)
H10	−0.0417	0.3902	0.3882	0.040*
C11	0.1169 (5)	0.5103 (9)	0.3793 (3)	0.0347 (14)
H11	0.1008	0.5841	0.3271	0.042*
C12	0.5830 (4)	0.2729 (8)	0.3932 (3)	0.0263 (13)
H12A	0.6173	0.3222	0.4482	0.032*
H12B	0.5617	0.3770	0.3551	0.032*
C13	0.6655 (4)	0.1593 (8)	0.3610 (3)	0.0285 (13)
C14	0.7705 (5)	0.1052 (10)	0.3911 (4)	0.0394 (16)
H14	0.8138	0.1352	0.4437	0.047*
C15	0.8039 (5)	−0.0051 (11)	0.3289 (4)	0.0503 (18)
H15	0.8741	−0.0634	0.3322	0.060*
C16	0.7198 (6)	−0.0120 (10)	0.2654 (5)	0.0526 (19)
H16	0.7197	−0.0781	0.2155	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pd1	0.0167 (3)	0.0232 (3)	0.0167 (3)	0.0001 (2)	−0.00344 (19)	−0.0002 (2)
Fe1	0.0187 (4)	0.0246 (5)	0.0207 (5)	0.0013 (4)	−0.0032 (3)	−0.0016 (4)
Cl1	0.0254 (7)	0.0275 (8)	0.0216 (7)	0.0012 (6)	−0.0039 (5)	−0.0054 (6)
O1	0.022 (2)	0.071 (3)	0.038 (3)	0.004 (2)	−0.0021 (19)	−0.019 (2)
N1	0.019 (2)	0.022 (3)	0.023 (3)	−0.0030 (19)	−0.0002 (19)	0.0001 (19)
C1	0.026 (3)	0.026 (3)	0.019 (3)	0.002 (2)	0.003 (2)	−0.001 (2)
C2	0.021 (3)	0.023 (3)	0.018 (3)	0.001 (2)	0.001 (2)	−0.003 (2)
C3	0.019 (3)	0.026 (3)	0.019 (3)	0.006 (3)	−0.002 (2)	0.000 (3)
C4	0.019 (3)	0.028 (4)	0.025 (3)	−0.001 (2)	−0.002 (2)	−0.001 (2)
C5	0.022 (3)	0.024 (3)	0.023 (3)	0.003 (2)	−0.006 (2)	−0.007 (2)
C6	0.022 (3)	0.030 (3)	0.018 (3)	0.006 (2)	−0.004 (2)	−0.004 (2)
C7	0.039 (3)	0.031 (4)	0.039 (4)	−0.011 (3)	0.006 (3)	−0.018 (3)
C8	0.032 (3)	0.040 (4)	0.022 (3)	0.002 (3)	−0.010 (3)	−0.012 (3)
C9	0.035 (3)	0.032 (4)	0.035 (4)	0.003 (3)	0.015 (3)	−0.005 (3)
C10	0.023 (3)	0.029 (4)	0.043 (4)	0.009 (3)	−0.004 (3)	−0.010 (3)
C11	0.049 (4)	0.027 (3)	0.026 (3)	0.014 (3)	−0.002 (3)	0.003 (3)
C12	0.027 (3)	0.031 (4)	0.019 (3)	−0.005 (2)	0.001 (2)	−0.003 (2)
C13	0.019 (3)	0.040 (4)	0.026 (3)	−0.004 (3)	0.002 (2)	0.002 (3)
C14	0.023 (3)	0.066 (5)	0.027 (4)	−0.001 (3)	0.003 (3)	0.009 (3)
C15	0.027 (3)	0.074 (5)	0.052 (4)	0.011 (4)	0.012 (3)	0.017 (4)
C16	0.035 (4)	0.070 (5)	0.054 (4)	0.011 (4)	0.011 (3)	−0.026 (4)

Geometric parameters (Å, º) top

Pd1—N1	2.021 (4)	C4—C5	1.420 (7)
Pd1—N1ⁱ	2.021 (4)	C4—H4	1.0000
Pd1—Cl1	2.3045 (13)	C5—C6	1.415 (8)
Pd1—Cl1ⁱ	2.3045 (13)	C5—H5	1.0000
Fe1—C2	2.034 (5)	C6—H6	1.0000
Fe1—C10	2.036 (6)	C7—C11	1.415 (8)
Fe1—C6	2.040 (5)	C7—C8	1.427 (8)
Fe1—C9	2.041 (6)	C7—H7	1.0000
Fe1—C3	2.044 (5)	C8—C9	1.421 (8)
Fe1—C5	2.046 (5)	C8—H8	1.0000
Fe1—C7	2.046 (6)	C9—C10	1.434 (8)
Fe1—C11	2.050 (6)	C9—H9	1.0000
Fe1—C4	2.053 (6)	C10—C11	1.413 (9)
Fe1—C8	2.065 (5)	C10—H10	1.0000
O1—C13	1.369 (6)	C11—H11	1.0000
O1—C16	1.390 (7)	C12—C13	1.478 (8)
N1—C1	1.295 (6)	C12—H12A	0.9900
N1—C12	1.468 (7)	C12—H12B	0.9900
C1—C2	1.445 (7)	C13—C14	1.346 (8)
C1—H1	0.9500	C14—C15	1.419 (9)
C2—C3	1.430 (7)	C14—H14	0.9500
C2—C6	1.451 (7)	C15—C16	1.320 (9)
C3—C4	1.420 (7)	C15—H15	0.9500
C3—H3	1.0000	C16—H16	0.9500

N1—Pd1—N1ⁱ	180.0 (2)	C2—C3—H3	126.2
N1—Pd1—Cl1	90.75 (13)	Fe1—C3—H3	126.2
N1ⁱ—Pd1—Cl1	89.25 (13)	C5—C4—C3	108.7 (5)
N1—Pd1—Cl1ⁱ	89.25 (13)	C5—C4—Fe1	69.5 (3)
N1ⁱ—Pd1—Cl1ⁱ	90.75 (13)	C3—C4—Fe1	69.4 (3)
Cl1—Pd1—Cl1ⁱ	180.0	C5—C4—H4	125.6
C2—Fe1—C10	167.2 (2)	C3—C4—H4	125.6
C2—Fe1—C6	41.74 (19)	Fe1—C4—H4	125.6
C10—Fe1—C6	127.5 (2)	C6—C5—C4	108.6 (4)
C2—Fe1—C9	150.6 (2)	C6—C5—Fe1	69.5 (3)
C10—Fe1—C9	41.2 (2)	C4—C5—Fe1	70.0 (3)
C6—Fe1—C9	166.4 (2)	C6—C5—H5	125.7
C2—Fe1—C3	41.0 (2)	C4—C5—H5	125.7
C10—Fe1—C3	150.1 (2)	Fe1—C5—H5	125.7
C6—Fe1—C3	69.4 (2)	C5—C6—C2	107.3 (5)
C9—Fe1—C3	117.1 (2)	C5—C6—Fe1	70.0 (3)
C2—Fe1—C5	68.9 (2)	C2—C6—Fe1	68.9 (3)
C10—Fe1—C5	107.0 (2)	C5—C6—H6	126.3
C6—Fe1—C5	40.5 (2)	C2—C6—H6	126.3
C9—Fe1—C5	128.5 (2)	Fe1—C6—H6	126.3
C3—Fe1—C5	68.7 (2)	C11—C7—C8	108.6 (5)
C2—Fe1—C7	108.9 (2)	C11—C7—Fe1	70.0 (3)
C10—Fe1—C7	68.2 (2)	C8—C7—Fe1	70.4 (3)
C6—Fe1—C7	117.6 (2)	C11—C7—H7	125.7
C9—Fe1—C7	68.4 (2)	C8—C7—H7	125.7
C3—Fe1—C7	130.3 (2)	Fe1—C7—H7	125.7
C5—Fe1—C7	150.1 (2)	C9—C8—C7	107.4 (5)
C2—Fe1—C11	129.4 (2)	C9—C8—Fe1	68.8 (3)
C10—Fe1—C11	40.5 (3)	C7—C8—Fe1	68.9 (3)
C6—Fe1—C11	107.4 (2)	C9—C8—H8	126.3
C9—Fe1—C11	68.6 (2)	C7—C8—H8	126.3
C3—Fe1—C11	168.5 (2)	Fe1—C8—H8	126.3
C5—Fe1—C11	116.6 (2)	C8—C9—C10	107.9 (5)
C7—Fe1—C11	40.4 (2)	C8—C9—Fe1	70.7 (3)
C2—Fe1—C4	68.5 (2)	C10—C9—Fe1	69.2 (3)
C10—Fe1—C4	116.8 (2)	C8—C9—H9	126.1
C6—Fe1—C4	68.5 (2)	C10—C9—H9	126.1
C9—Fe1—C4	108.1 (2)	Fe1—C9—H9	126.1
C3—Fe1—C4	40.5 (2)	C11—C10—C9	108.0 (5)
C5—Fe1—C4	40.5 (2)	C11—C10—Fe1	70.3 (4)
C7—Fe1—C4	168.6 (2)	C9—C10—Fe1	69.6 (3)
C11—Fe1—C4	149.7 (2)	C11—C10—H10	126.0
C2—Fe1—C8	118.0 (2)	C9—C10—H10	126.0
C10—Fe1—C8	68.5 (2)	Fe1—C10—H10	126.0
C6—Fe1—C8	151.5 (2)	C10—C11—C7	108.1 (5)
C9—Fe1—C8	40.5 (2)	C10—C11—Fe1	69.2 (4)
C3—Fe1—C8	109.0 (2)	C7—C11—Fe1	69.6 (3)
C5—Fe1—C8	167.4 (2)	C10—C11—H11	126.0
C7—Fe1—C8	40.6 (2)	C7—C11—H11	126.0
C11—Fe1—C8	68.2 (2)	Fe1—C11—H11	126.0
C4—Fe1—C8	129.8 (2)	N1—C12—C13	111.9 (5)
C13—O1—C16	105.9 (5)	N1—C12—H12A	109.2
C1—N1—C12	116.9 (5)	C13—C12—H12A	109.2
C1—N1—Pd1	127.9 (4)	N1—C12—H12B	109.2
C12—N1—Pd1	115.1 (3)	C13—C12—H12B	109.2
N1—C1—C2	127.6 (5)	H12A—C12—H12B	107.9
N1—C1—H1	116.2	C14—C13—O1	109.9 (5)
C2—C1—H1	116.2	C14—C13—C12	134.6 (6)
C3—C2—C1	130.9 (5)	O1—C13—C12	115.5 (4)
C3—C2—C6	107.7 (5)	C13—C14—C15	106.6 (5)
C1—C2—C6	120.8 (5)	C13—C14—H14	126.7
C3—C2—Fe1	69.9 (3)	C15—C14—H14	126.7
C1—C2—Fe1	119.3 (4)	C16—C15—C14	107.5 (6)
C6—C2—Fe1	69.3 (3)	C16—C15—H15	126.2
C4—C3—C2	107.7 (4)	C14—C15—H15	126.2
C4—C3—Fe1	70.0 (3)	C15—C16—O1	110.0 (6)
C2—C3—Fe1	69.1 (3)	C15—C16—H16	125.0
C4—C3—H3	126.2	O1—C16—H16	125.0

Cl1—Pd1—N1—C1	75.8 (5)	C5—Fe1—C6—C2	−118.7 (5)
Cl1ⁱ—Pd1—N1—C1	−104.2 (5)	C7—Fe1—C6—C2	87.9 (4)
Cl1—Pd1—N1—C12	−106.5 (4)	C11—Fe1—C6—C2	130.4 (3)
Cl1ⁱ—Pd1—N1—C12	73.5 (4)	C4—Fe1—C6—C2	−81.4 (3)
C12—N1—C1—C2	178.8 (5)	C8—Fe1—C6—C2	54.2 (6)
Pd1—N1—C1—C2	−3.5 (8)	C2—Fe1—C7—C11	129.3 (4)
N1—C1—C2—C3	9.7 (10)	C10—Fe1—C7—C11	−37.4 (4)
N1—C1—C2—C6	179.8 (5)	C6—Fe1—C7—C11	84.6 (4)
N1—C1—C2—Fe1	97.6 (6)	C9—Fe1—C7—C11	−81.9 (4)
C10—Fe1—C2—C3	−154.9 (9)	C3—Fe1—C7—C11	170.3 (3)
C6—Fe1—C2—C3	−118.9 (4)	C5—Fe1—C7—C11	48.9 (6)
C9—Fe1—C2—C3	51.3 (6)	C4—Fe1—C7—C11	−155.9 (11)
C5—Fe1—C2—C3	−81.3 (3)	C8—Fe1—C7—C11	−119.3 (5)
C7—Fe1—C2—C3	130.5 (3)	C2—Fe1—C7—C8	−111.3 (4)
C11—Fe1—C2—C3	171.0 (3)	C10—Fe1—C7—C8	81.9 (4)
C4—Fe1—C2—C3	−37.7 (3)	C6—Fe1—C7—C8	−156.0 (3)
C8—Fe1—C2—C3	87.1 (3)	C9—Fe1—C7—C8	37.4 (3)
C10—Fe1—C2—C1	78.6 (11)	C3—Fe1—C7—C8	−70.4 (4)
C6—Fe1—C2—C1	114.6 (6)	C5—Fe1—C7—C8	168.3 (4)
C9—Fe1—C2—C1	−75.2 (7)	C11—Fe1—C7—C8	119.3 (5)
C3—Fe1—C2—C1	−126.5 (5)	C4—Fe1—C7—C8	−36.5 (14)
C5—Fe1—C2—C1	152.2 (5)	C11—C7—C8—C9	1.6 (7)
C7—Fe1—C2—C1	4.0 (5)	Fe1—C7—C8—C9	−58.2 (4)
C11—Fe1—C2—C1	44.5 (5)	C11—C7—C8—Fe1	59.8 (4)
C4—Fe1—C2—C1	−164.1 (5)	C2—Fe1—C8—C9	−153.7 (3)
C8—Fe1—C2—C1	−39.4 (5)	C10—Fe1—C8—C9	38.4 (4)
C10—Fe1—C2—C6	−36.0 (11)	C6—Fe1—C8—C9	168.5 (4)
C9—Fe1—C2—C6	170.2 (4)	C3—Fe1—C8—C9	−109.8 (4)
C3—Fe1—C2—C6	118.9 (4)	C5—Fe1—C8—C9	−32.8 (12)
C5—Fe1—C2—C6	37.6 (3)	C7—Fe1—C8—C9	119.6 (5)
C7—Fe1—C2—C6	−110.6 (4)	C11—Fe1—C8—C9	82.1 (4)
C11—Fe1—C2—C6	−70.1 (4)	C4—Fe1—C8—C9	−69.3 (4)
C4—Fe1—C2—C6	81.3 (3)	C2—Fe1—C8—C7	86.7 (4)
C8—Fe1—C2—C6	−154.0 (3)	C10—Fe1—C8—C7	−81.2 (4)
C1—C2—C3—C4	171.5 (5)	C6—Fe1—C8—C7	49.0 (6)
C6—C2—C3—C4	0.4 (6)	C9—Fe1—C8—C7	−119.6 (5)
Fe1—C2—C3—C4	59.6 (4)	C3—Fe1—C8—C7	130.6 (3)
C1—C2—C3—Fe1	111.8 (6)	C5—Fe1—C8—C7	−152.4 (9)
C6—C2—C3—Fe1	−59.3 (4)	C11—Fe1—C8—C7	−37.5 (4)
C2—Fe1—C3—C4	−119.0 (4)	C4—Fe1—C8—C7	171.2 (3)
C10—Fe1—C3—C4	50.1 (5)	C7—C8—C9—C10	−1.2 (6)
C6—Fe1—C3—C4	−80.5 (3)	Fe1—C8—C9—C10	−59.5 (4)
C9—Fe1—C3—C4	86.5 (4)	C7—C8—C9—Fe1	58.3 (4)
C5—Fe1—C3—C4	−37.0 (3)	C2—Fe1—C9—C8	52.8 (6)
C7—Fe1—C3—C4	170.2 (3)	C10—Fe1—C9—C8	−118.7 (5)
C11—Fe1—C3—C4	−156.4 (10)	C6—Fe1—C9—C8	−156.1 (9)
C8—Fe1—C3—C4	129.8 (3)	C3—Fe1—C9—C8	87.9 (4)
C10—Fe1—C3—C2	169.1 (4)	C5—Fe1—C9—C8	171.3 (3)
C6—Fe1—C3—C2	38.5 (3)	C7—Fe1—C9—C8	−37.5 (4)
C9—Fe1—C3—C2	−154.5 (3)	C11—Fe1—C9—C8	−81.1 (4)
C5—Fe1—C3—C2	82.0 (3)	C4—Fe1—C9—C8	130.9 (3)
C7—Fe1—C3—C2	−70.8 (4)	C2—Fe1—C9—C10	171.5 (4)
C11—Fe1—C3—C2	−37.4 (11)	C6—Fe1—C9—C10	−37.4 (12)
C4—Fe1—C3—C2	119.0 (4)	C3—Fe1—C9—C10	−153.4 (3)
C8—Fe1—C3—C2	−111.2 (3)	C5—Fe1—C9—C10	−70.0 (4)
C2—C3—C4—C5	−0.6 (6)	C7—Fe1—C9—C10	81.2 (4)
Fe1—C3—C4—C5	58.5 (4)	C11—Fe1—C9—C10	37.6 (4)
C2—C3—C4—Fe1	−59.0 (4)	C4—Fe1—C9—C10	−110.4 (4)
C2—Fe1—C4—C5	−82.3 (3)	C8—Fe1—C9—C10	118.7 (5)
C10—Fe1—C4—C5	84.9 (4)	C8—C9—C10—C11	0.4 (7)
C6—Fe1—C4—C5	−37.3 (3)	Fe1—C9—C10—C11	−60.0 (4)
C9—Fe1—C4—C5	128.7 (3)	C8—C9—C10—Fe1	60.4 (4)
C3—Fe1—C4—C5	−120.4 (5)	C2—Fe1—C10—C11	−41.9 (11)
C7—Fe1—C4—C5	−161.3 (11)	C6—Fe1—C10—C11	−71.4 (4)
C11—Fe1—C4—C5	50.5 (6)	C9—Fe1—C10—C11	118.9 (5)
C8—Fe1—C4—C5	168.5 (3)	C3—Fe1—C10—C11	172.1 (4)
C2—Fe1—C4—C3	38.1 (3)	C5—Fe1—C10—C11	−111.3 (4)
C10—Fe1—C4—C3	−154.6 (3)	C7—Fe1—C10—C11	37.4 (3)
C6—Fe1—C4—C3	83.1 (3)	C4—Fe1—C10—C11	−153.9 (3)
C9—Fe1—C4—C3	−110.8 (3)	C8—Fe1—C10—C11	81.2 (4)
C5—Fe1—C4—C3	120.4 (5)	C2—Fe1—C10—C9	−160.8 (9)
C7—Fe1—C4—C3	−40.8 (13)	C6—Fe1—C10—C9	169.6 (3)
C11—Fe1—C4—C3	170.9 (4)	C3—Fe1—C10—C9	53.2 (6)
C8—Fe1—C4—C3	−71.1 (4)	C5—Fe1—C10—C9	129.8 (4)
C3—C4—C5—C6	0.5 (6)	C7—Fe1—C10—C9	−81.6 (4)
Fe1—C4—C5—C6	59.0 (4)	C11—Fe1—C10—C9	−118.9 (5)
C3—C4—C5—Fe1	−58.5 (4)	C4—Fe1—C10—C9	87.2 (4)
C2—Fe1—C5—C6	−38.7 (3)	C8—Fe1—C10—C9	−37.7 (4)
C10—Fe1—C5—C6	128.5 (3)	C9—C10—C11—C7	0.6 (7)
C9—Fe1—C5—C6	168.8 (3)	Fe1—C10—C11—C7	−59.0 (4)
C3—Fe1—C5—C6	−82.9 (3)	C9—C10—C11—Fe1	59.6 (4)
C7—Fe1—C5—C6	52.8 (6)	C8—C7—C11—C10	−1.3 (7)
C11—Fe1—C5—C6	85.9 (4)	Fe1—C7—C11—C10	58.7 (4)
C4—Fe1—C5—C6	−119.9 (4)	C8—C7—C11—Fe1	−60.1 (4)
C8—Fe1—C5—C6	−164.5 (9)	C2—Fe1—C11—C10	169.0 (3)
C2—Fe1—C5—C4	81.2 (3)	C6—Fe1—C11—C10	128.0 (3)
C10—Fe1—C5—C4	−111.7 (4)	C9—Fe1—C11—C10	−38.3 (3)
C6—Fe1—C5—C4	119.9 (4)	C3—Fe1—C11—C10	−159.9 (9)
C9—Fe1—C5—C4	−71.3 (4)	C5—Fe1—C11—C10	85.2 (4)
C3—Fe1—C5—C4	37.0 (3)	C7—Fe1—C11—C10	−119.6 (5)
C7—Fe1—C5—C4	172.7 (4)	C4—Fe1—C11—C10	51.1 (6)
C11—Fe1—C5—C4	−154.2 (3)	C8—Fe1—C11—C10	−82.0 (4)
C8—Fe1—C5—C4	−44.6 (11)	C2—Fe1—C11—C7	−71.4 (4)
C4—C5—C6—C2	−0.3 (6)	C10—Fe1—C11—C7	119.6 (5)
Fe1—C5—C6—C2	59.0 (4)	C6—Fe1—C11—C7	−112.4 (4)
C4—C5—C6—Fe1	−59.3 (4)	C9—Fe1—C11—C7	81.4 (4)
C3—C2—C6—C5	−0.1 (6)	C3—Fe1—C11—C7	−40.3 (12)
C1—C2—C6—C5	−172.2 (5)	C5—Fe1—C11—C7	−155.2 (4)
Fe1—C2—C6—C5	−59.7 (4)	C4—Fe1—C11—C7	170.8 (4)
C3—C2—C6—Fe1	59.6 (4)	C8—Fe1—C11—C7	37.7 (4)
C1—C2—C6—Fe1	−112.6 (5)	C1—N1—C12—C13	−105.6 (6)
C2—Fe1—C6—C5	118.7 (5)	Pd1—N1—C12—C13	76.5 (5)
C10—Fe1—C6—C5	−70.7 (4)	C16—O1—C13—C14	1.4 (7)
C9—Fe1—C6—C5	−40.4 (11)	C16—O1—C13—C12	−179.1 (5)
C3—Fe1—C6—C5	80.9 (3)	N1—C12—C13—C14	−117.7 (7)
C7—Fe1—C6—C5	−153.4 (3)	N1—C12—C13—O1	62.9 (7)
C11—Fe1—C6—C5	−110.8 (3)	O1—C13—C14—C15	−1.0 (7)
C4—Fe1—C6—C5	37.3 (3)	C12—C13—C14—C15	179.6 (7)
C8—Fe1—C6—C5	173.0 (4)	C13—C14—C15—C16	0.2 (8)
C10—Fe1—C6—C2	170.6 (3)	C14—C15—C16—O1	0.7 (9)
C9—Fe1—C6—C2	−159.1 (9)	C13—O1—C16—C15	−1.3 (8)
C3—Fe1—C6—C2	−37.9 (3)

Symmetry code: (i) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	[Fe₂Pd(C₅H₅)₂(C₁₁H₁₀NO)₂Cl₂]
M_r	763.58
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	12.2113 (7), 7.3439 (5), 16.365 (1)
β (°)	100.616 (4)
V (Å³)	1442.44 (16)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	14.91
Crystal size (mm)	0.44 × 0.07 × 0.04

Data collection
Diffractometer	Bruker SMART CCD APEXII area-detector
Absorption correction	Numerical (SADABS; Sheldrick, 2008a; Parkin et al., 1995)
T_min, T_max	0.059, 0.560
No. of measured, independent and observed [I > 2σ(I)] reflections	12086, 2598, 1886
R_int	0.088
(sin θ/λ)_max (Å⁻¹)	0.616

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.109, 1.02
No. of reflections	2598
No. of parameters	187
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.85, −1.01

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008b).

Acknowledgements

The authors acknowledge support by NSF–CRIF grant No. 0443538, NRF Thuthuka and Mobility Travel Grant and UWC Senate Research.

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