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In the title compound, [PdCl2{(η5-C4H4N)(η5-C5H5)Fe}2], the PdII atom lies on an inversion center in a slightly distorted square-planar arrangement of cis Cl and N ligands. The aza­ferrocene ligands display a typical sandwich structure with practically parallel Cp and pyrrolyl rings. Weak hydrogen-bond inter­actions (C—H...Cl) are found in the structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806026729/jh2024sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806026729/jh2024Isup2.hkl
Contains datablock I

CCDC reference: 618249

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.032
  • wR factor = 0.087
  • Data-to-parameter ratio = 16.9

checkCIF/PLATON results

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Alert level G ABSTM02_ALERT_3_G The ratio of expected to reported Tmax/Tmin(RR) is > 1.10 Tmin and Tmax reported: 0.674 0.896 Tmin and Tmax expected: 0.547 0.880 RR = 1.209 Please check that your absorption correction is appropriate.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2004); program(s) used to solve structure: XS in SHELXTL (Bruker, 1999); program(s) used to refine structure: XL in SHELXTL; molecular graphics: XP in SHELXTL; software used to prepare material for publication: SHELXTL.

trans-Bis(azaferrocene)dichloropalladium(II) top
Crystal data top
[Fe2Pd(C5H5)2(C4H4N)2]F(000) = 1088
Mr = 551.34Dx = 2.055 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 5832 reflections
a = 9.574 (4) Åθ = 2–26°
b = 11.592 (5) ŵ = 2.91 mm1
c = 16.060 (5) ÅT = 100 K
V = 1782.4 (12) Å3Plate, black
Z = 40.21 × 0.18 × 0.04 mm
Data collection top
Kuma KM-4 CCD kappa-axis
diffractometer
1940 independent reflections
Radiation source: fine-focus sealed tube1788 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.075
ω scansθmax = 27.0°, θmin = 3.3°
Absorption correction: analytical
(CrysAlis CCD; Oxford Diffraction, 2004)
h = 1212
Tmin = 0.674, Tmax = 0.896k = 149
10701 measured reflectionsl = 2020
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)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087H-atom parameters constrained
S = 1.14 w = 1/[σ2(Fo2) + (0.0517P)2 + 1.2026P]
where P = (Fo2 + 2Fc2)/3
1940 reflections(Δ/σ)max < 0.001
115 parametersΔρmax = 1.33 e Å3
0 restraintsΔρmin = 0.70 e Å3
Special details top

Experimental. 1H NMR (200 MHz, CDCl3): δ 6.67 (s, 2H, pyrrolyl), 4.68 (s, 2H, pyrrolyl), 4.61 (s, 5H, Cp).

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
xyzUiso*/Ueq
Pd0.00000.00000.00000.01211 (13)
Fe0.16824 (4)0.22393 (3)0.11756 (2)0.01327 (14)
Cl0.13919 (8)0.01980 (6)0.11628 (5)0.02414 (19)
N0.0333 (2)0.16912 (19)0.03032 (15)0.0156 (4)
C110.0379 (3)0.2334 (2)0.09077 (18)0.0172 (5)
H110.10960.20590.12440.021*
C120.0167 (3)0.3473 (3)0.0926 (2)0.0205 (6)
H120.01220.40700.12720.025*
C130.1233 (3)0.3528 (2)0.03179 (18)0.0198 (6)
H130.17750.41690.01870.024*
C140.1321 (3)0.2423 (2)0.00551 (16)0.0171 (6)
H140.19430.22170.04750.020*
C210.2518 (3)0.0795 (2)0.17301 (17)0.0207 (6)
H210.23060.00310.16080.025*
C220.1841 (3)0.1491 (3)0.23261 (17)0.0232 (6)
H220.10980.12660.26610.028*
C230.2485 (3)0.2592 (2)0.2328 (2)0.0234 (7)
H230.22410.32120.26660.028*
C240.3574 (3)0.2581 (3)0.1722 (2)0.0231 (6)
H240.41680.31910.15950.028*
C250.3587 (3)0.1468 (2)0.13462 (18)0.0203 (6)
H250.41860.12230.09260.024*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pd0.01166 (19)0.0112 (2)0.01351 (19)0.00282 (9)0.00122 (9)0.00050 (9)
Fe0.0128 (2)0.0110 (2)0.0161 (2)0.00033 (13)0.00126 (14)0.00128 (13)
Cl0.0315 (4)0.0178 (3)0.0231 (4)0.0048 (3)0.0134 (3)0.0013 (3)
N0.0150 (10)0.0145 (11)0.0174 (11)0.0020 (9)0.0012 (9)0.0012 (9)
C110.0142 (12)0.0147 (13)0.0226 (14)0.0019 (10)0.0027 (10)0.0037 (11)
C120.0189 (13)0.0143 (13)0.0282 (15)0.0033 (10)0.0066 (11)0.0017 (11)
C130.0218 (13)0.0146 (13)0.0231 (14)0.0030 (10)0.0081 (11)0.0021 (11)
C140.0168 (13)0.0157 (13)0.0187 (13)0.0051 (11)0.0031 (10)0.0023 (10)
C210.0215 (13)0.0158 (13)0.0248 (13)0.0034 (11)0.0034 (11)0.0017 (11)
C220.0263 (14)0.0249 (15)0.0184 (13)0.0080 (12)0.0008 (11)0.0071 (11)
C230.0270 (17)0.0218 (16)0.0214 (14)0.0092 (12)0.0105 (11)0.0057 (11)
C240.0205 (14)0.0159 (13)0.0331 (16)0.0007 (11)0.0138 (12)0.0010 (12)
C250.0143 (12)0.0195 (13)0.0271 (15)0.0035 (10)0.0018 (10)0.0007 (11)
Geometric parameters (Å, º) top
Pd—Ni2.045 (2)C11—H110.9300
Pd—N2.045 (2)C12—C131.413 (4)
Pd—Cli2.3057 (9)C12—H120.9300
Pd—Cl2.3057 (9)C13—C141.417 (4)
Fe—N2.009 (2)C13—H130.9300
Fe—C142.018 (3)C14—H140.9300
Fe—C112.023 (3)C21—C221.410 (4)
Fe—C232.046 (3)C21—C251.426 (4)
Fe—C222.047 (3)C21—H210.9300
Fe—C252.050 (3)C22—C231.417 (4)
Fe—C242.051 (3)C22—H220.9300
Fe—C212.058 (3)C23—C241.427 (4)
Fe—C122.076 (3)C23—H230.9300
Fe—C132.077 (3)C24—C251.425 (4)
N—C141.394 (4)C24—H240.9300
N—C111.401 (4)C25—H250.9300
C11—C121.420 (4)
Ni—Pd—N180.00 (13)Fe—N—Pd124.73 (12)
Ni—Pd—Cli89.58 (7)N—C11—C12109.2 (3)
N—Pd—Cli90.42 (7)N—C11—Fe69.14 (15)
Ni—Pd—Cl90.42 (7)C12—C11—Fe71.76 (16)
N—Pd—Cl89.58 (7)N—C11—H11125.4
Cli—Pd—Cl180.00 (2)C12—C11—H11125.4
N—Fe—C1440.52 (10)Fe—C11—H11125.3
N—Fe—C1140.67 (10)C13—C12—C11107.1 (3)
C14—Fe—C1167.58 (12)C13—C12—Fe70.14 (16)
N—Fe—C23159.37 (12)C11—C12—Fe67.71 (16)
C14—Fe—C23158.42 (12)C13—C12—H12126.5
C11—Fe—C23123.24 (11)C11—C12—H12126.5
N—Fe—C22122.92 (11)Fe—C12—H12127.2
C14—Fe—C22160.33 (12)C12—C13—C14107.1 (2)
C11—Fe—C22106.72 (12)C12—C13—Fe70.07 (16)
C23—Fe—C2240.50 (12)C14—C13—Fe67.53 (15)
N—Fe—C25121.82 (11)C12—C13—H13126.4
C14—Fe—C25109.23 (12)C14—C13—H13126.4
C11—Fe—C25156.95 (11)Fe—C13—H13127.5
C23—Fe—C2568.40 (11)N—C14—C13109.6 (3)
C22—Fe—C2568.17 (11)N—C14—Fe69.39 (14)
N—Fe—C24158.02 (11)C13—C14—Fe72.02 (16)
C14—Fe—C24123.38 (13)N—C14—H14125.2
C11—Fe—C24160.37 (12)C13—C14—H14125.2
C23—Fe—C2440.76 (12)Fe—C14—H14125.0
C22—Fe—C2468.28 (13)C22—C21—C25108.1 (2)
C25—Fe—C2440.68 (11)C22—C21—Fe69.48 (15)
N—Fe—C21107.13 (10)C25—C21—Fe69.36 (16)
C14—Fe—C21125.18 (12)C22—C21—H21126.0
C11—Fe—C21121.04 (11)C25—C21—H21126.0
C23—Fe—C2167.95 (11)Fe—C21—H21126.8
C22—Fe—C2140.16 (11)C21—C22—C23108.5 (3)
C25—Fe—C2140.64 (11)C21—C22—Fe70.35 (16)
C24—Fe—C2168.21 (11)C23—C22—Fe69.70 (17)
N—Fe—C1268.52 (11)C21—C22—H22125.8
C14—Fe—C1267.57 (12)C23—C22—H22125.8
C11—Fe—C1240.53 (11)Fe—C22—H22125.8
C23—Fe—C12107.45 (12)C22—C23—C24108.0 (3)
C22—Fe—C12121.22 (12)C22—C23—Fe69.79 (16)
C25—Fe—C12161.46 (11)C24—C23—Fe69.83 (17)
C24—Fe—C12124.50 (12)C22—C23—H23126.0
C21—Fe—C12156.29 (12)C24—C23—H23126.0
N—Fe—C1368.39 (10)Fe—C23—H23125.9
C14—Fe—C1340.45 (11)C25—C24—C23107.6 (3)
C11—Fe—C1367.53 (11)C25—C24—Fe69.60 (16)
C23—Fe—C13122.31 (11)C23—C24—Fe69.41 (16)
C22—Fe—C13156.76 (11)C25—C24—H24126.2
C25—Fe—C13125.93 (11)C23—C24—H24126.2
C24—Fe—C13109.12 (12)Fe—C24—H24126.4
C21—Fe—C13162.26 (12)C24—C25—C21107.8 (3)
C12—Fe—C1339.80 (12)C24—C25—Fe69.72 (16)
C14—N—C11107.0 (2)C21—C25—Fe70.00 (16)
C14—N—Fe70.08 (14)C24—C25—H25126.1
C11—N—Fe70.20 (15)C21—C25—H25126.1
C14—N—Pd126.19 (19)Fe—C25—H25125.7
C11—N—Pd126.81 (18)
C11—Fe—N—C14117.5 (2)C13—Fe—C14—N119.9 (2)
C23—Fe—N—C14162.7 (3)N—Fe—C14—C13119.9 (2)
C22—Fe—N—C14165.70 (17)C11—Fe—C14—C1381.17 (18)
C25—Fe—N—C1482.57 (19)C23—Fe—C14—C1343.5 (4)
C24—Fe—N—C1450.5 (3)C22—Fe—C14—C13157.9 (3)
C21—Fe—N—C14124.56 (17)C25—Fe—C14—C13123.28 (18)
C12—Fe—N—C1480.16 (18)C24—Fe—C14—C1380.3 (2)
C13—Fe—N—C1437.23 (17)C21—Fe—C14—C13165.77 (17)
C14—Fe—N—C11117.5 (2)C12—Fe—C14—C1337.17 (17)
C23—Fe—N—C1145.2 (3)N—Fe—C21—C22121.09 (17)
C22—Fe—N—C1176.84 (18)C14—Fe—C21—C22161.99 (17)
C25—Fe—N—C11159.97 (16)C11—Fe—C21—C2278.9 (2)
C24—Fe—N—C11167.9 (3)C23—Fe—C21—C2237.62 (18)
C21—Fe—N—C11117.98 (17)C25—Fe—C21—C22119.7 (2)
C12—Fe—N—C1137.30 (16)C24—Fe—C21—C2281.72 (19)
C13—Fe—N—C1180.22 (17)C12—Fe—C21—C2245.6 (4)
C14—Fe—N—Pd120.9 (2)C13—Fe—C21—C22166.4 (3)
C11—Fe—N—Pd121.7 (2)N—Fe—C21—C25119.21 (17)
C23—Fe—N—Pd76.5 (3)C14—Fe—C21—C2578.3 (2)
C22—Fe—N—Pd44.84 (19)C11—Fe—C21—C25161.41 (16)
C25—Fe—N—Pd38.29 (19)C23—Fe—C21—C2582.07 (18)
C24—Fe—N—Pd70.4 (3)C22—Fe—C21—C25119.7 (2)
C21—Fe—N—Pd3.70 (17)C24—Fe—C21—C2537.98 (17)
C12—Fe—N—Pd158.98 (18)C12—Fe—C21—C25165.3 (3)
C13—Fe—N—Pd158.10 (17)C13—Fe—C21—C2546.7 (4)
Cli—Pd—N—C1411.4 (2)C25—C21—C22—C230.7 (3)
Cl—Pd—N—C14168.6 (2)Fe—C21—C22—C2359.49 (19)
Cli—Pd—N—C11168.7 (2)C25—C21—C22—Fe58.78 (19)
Cl—Pd—N—C1111.3 (2)N—Fe—C22—C2177.12 (19)
Cli—Pd—N—Fe101.06 (13)C14—Fe—C22—C2148.7 (4)
Cl—Pd—N—Fe78.94 (13)C11—Fe—C22—C21118.61 (17)
C14—N—C11—C120.1 (3)C23—Fe—C22—C21119.4 (2)
Fe—N—C11—C1260.80 (19)C25—Fe—C22—C2137.55 (17)
Pd—N—C11—C12179.93 (18)C24—Fe—C22—C2181.51 (18)
C14—N—C11—Fe60.74 (18)C12—Fe—C22—C21160.37 (17)
Pd—N—C11—Fe119.13 (19)C13—Fe—C22—C21169.6 (3)
C14—Fe—C11—N38.59 (15)N—Fe—C22—C23163.47 (16)
C23—Fe—C11—N162.61 (15)C14—Fe—C22—C23168.1 (3)
C22—Fe—C11—N121.41 (16)C11—Fe—C22—C23121.98 (17)
C25—Fe—C11—N48.0 (4)C25—Fe—C22—C2381.86 (18)
C24—Fe—C11—N166.5 (3)C24—Fe—C22—C2337.90 (17)
C21—Fe—C11—N80.04 (18)C21—Fe—C22—C23119.4 (2)
C12—Fe—C11—N119.8 (2)C12—Fe—C22—C2380.23 (19)
C13—Fe—C11—N82.52 (17)C13—Fe—C22—C2350.2 (3)
N—Fe—C11—C12119.8 (2)C21—C22—C23—C240.3 (3)
C14—Fe—C11—C1281.21 (19)Fe—C22—C23—C2459.6 (2)
C23—Fe—C11—C1277.6 (2)C21—C22—C23—Fe59.89 (19)
C22—Fe—C11—C12118.79 (19)N—Fe—C23—C2242.7 (4)
C25—Fe—C11—C12167.8 (3)C14—Fe—C23—C22169.1 (3)
C24—Fe—C11—C1246.7 (4)C11—Fe—C23—C2276.24 (19)
C21—Fe—C11—C12160.16 (17)C25—Fe—C23—C2281.24 (17)
C13—Fe—C11—C1237.28 (18)C24—Fe—C23—C22119.1 (2)
N—C11—C12—C130.2 (3)C21—Fe—C23—C2237.32 (16)
Fe—C11—C12—C1359.34 (19)C12—Fe—C23—C22117.94 (17)
N—C11—C12—Fe59.19 (18)C13—Fe—C23—C22158.99 (16)
N—Fe—C12—C1381.60 (17)N—Fe—C23—C24161.7 (3)
C14—Fe—C12—C1337.76 (17)C14—Fe—C23—C2450.0 (4)
C11—Fe—C12—C13119.0 (2)C11—Fe—C23—C24164.70 (16)
C23—Fe—C12—C13119.87 (18)C22—Fe—C23—C24119.1 (2)
C22—Fe—C12—C13162.01 (16)C25—Fe—C23—C2437.81 (17)
C25—Fe—C12—C1345.9 (4)C21—Fe—C23—C2481.74 (18)
C24—Fe—C12—C1378.2 (2)C12—Fe—C23—C24123.00 (17)
C21—Fe—C12—C13165.4 (2)C13—Fe—C23—C2481.95 (19)
N—Fe—C12—C1137.42 (16)C22—C23—C24—C250.3 (3)
C14—Fe—C12—C1181.26 (18)Fe—C23—C24—C2559.33 (19)
C23—Fe—C12—C11121.10 (18)C22—C23—C24—Fe59.6 (2)
C22—Fe—C12—C1179.0 (2)N—Fe—C24—C2543.8 (4)
C25—Fe—C12—C11164.9 (3)C14—Fe—C24—C2580.7 (2)
C24—Fe—C12—C11162.74 (18)C11—Fe—C24—C25160.1 (3)
C21—Fe—C12—C1146.3 (4)C23—Fe—C24—C25119.0 (2)
C13—Fe—C12—C11119.0 (2)C22—Fe—C24—C2581.34 (19)
C11—C12—C13—C140.3 (3)C21—Fe—C24—C2537.94 (17)
Fe—C12—C13—C1457.51 (19)C12—Fe—C24—C25164.88 (17)
C11—C12—C13—Fe57.81 (19)C13—Fe—C24—C25123.33 (18)
N—Fe—C13—C1281.97 (18)N—Fe—C24—C23162.8 (3)
C14—Fe—C13—C12119.3 (2)C14—Fe—C24—C23160.27 (17)
C11—Fe—C13—C1237.94 (17)C11—Fe—C24—C2341.1 (4)
C23—Fe—C13—C1278.2 (2)C22—Fe—C24—C2337.67 (17)
C22—Fe—C13—C1242.0 (4)C25—Fe—C24—C23119.0 (2)
C25—Fe—C13—C12163.62 (17)C21—Fe—C24—C2381.07 (18)
C24—Fe—C13—C12121.35 (18)C12—Fe—C24—C2376.1 (2)
C21—Fe—C13—C12160.5 (3)C13—Fe—C24—C23117.66 (18)
N—Fe—C13—C1437.30 (17)C23—C24—C25—C210.7 (3)
C11—Fe—C13—C1481.32 (18)Fe—C24—C25—C2159.91 (19)
C23—Fe—C13—C14162.56 (17)C23—C24—C25—Fe59.21 (19)
C22—Fe—C13—C14161.3 (3)C22—C21—C25—C240.9 (3)
C25—Fe—C13—C1477.1 (2)Fe—C21—C25—C2459.73 (19)
C24—Fe—C13—C14119.39 (19)C22—C21—C25—Fe58.86 (19)
C21—Fe—C13—C1441.3 (4)N—Fe—C25—C24162.24 (17)
C12—Fe—C13—C14119.3 (2)C14—Fe—C25—C24119.21 (19)
C11—N—C14—C130.3 (3)C11—Fe—C25—C24163.0 (3)
Fe—N—C14—C1361.07 (19)C23—Fe—C25—C2437.88 (18)
Pd—N—C14—C13179.87 (18)C22—Fe—C25—C2481.6 (2)
C11—N—C14—Fe60.81 (18)C21—Fe—C25—C24118.8 (2)
Pd—N—C14—Fe119.06 (19)C12—Fe—C25—C2442.6 (4)
C12—C13—C14—N0.4 (3)C13—Fe—C25—C2477.1 (2)
Fe—C13—C14—N59.46 (19)N—Fe—C25—C2179.00 (18)
C12—C13—C14—Fe59.1 (2)C14—Fe—C25—C21122.04 (17)
C11—Fe—C14—N38.72 (15)C11—Fe—C25—C2144.3 (4)
C23—Fe—C14—N163.4 (3)C23—Fe—C25—C2180.87 (18)
C22—Fe—C14—N38.0 (4)C22—Fe—C25—C2137.12 (17)
C25—Fe—C14—N116.83 (17)C24—Fe—C25—C21118.8 (2)
C24—Fe—C14—N159.77 (15)C12—Fe—C25—C21161.3 (3)
C21—Fe—C14—N74.34 (19)C13—Fe—C25—C21164.10 (16)
C12—Fe—C14—N82.73 (17)
Symmetry code: (i) x, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C23—H23···Clii0.932.763.678 (3)171
Symmetry code: (ii) x, y1/2, z+1/2.
 

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