In the title compound, [PdCl
2{(η5-C
4H
4N)(η5-C
5H
5)Fe}
2], the Pd
II 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
CCDC reference: 618249
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.004 Å
- R factor = 0.032
- wR factor = 0.087
- Data-to-parameter ratio = 16.9
checkCIF/PLATON results
No syntax errors found
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
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 = 551.34 | Dx = 2.055 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 5832 reflections |
a = 9.574 (4) Å | θ = 2–26° |
b = 11.592 (5) Å | µ = 2.91 mm−1 |
c = 16.060 (5) Å | T = 100 K |
V = 1782.4 (12) Å3 | Plate, black |
Z = 4 | 0.21 × 0.18 × 0.04 mm |
Data collection top
Kuma KM-4 CCD kappa-axis diffractometer | 1940 independent reflections |
Radiation source: fine-focus sealed tube | 1788 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.075 |
ω scans | θmax = 27.0°, θmin = 3.3° |
Absorption correction: analytical (CrysAlis CCD; Oxford Diffraction, 2004) | h = −12→12 |
Tmin = 0.674, Tmax = 0.896 | k = −14→9 |
10701 measured reflections | l = −20→20 |
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)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.087 | H-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 parameters | Δρmax = 1.33 e Å−3 |
0 restraints | Δρmin = −0.70 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
Pd | 0.0000 | 0.0000 | 0.0000 | 0.01211 (13) | |
Fe | −0.16824 (4) | −0.22393 (3) | 0.11756 (2) | 0.01327 (14) | |
Cl | 0.13919 (8) | 0.01980 (6) | 0.11628 (5) | 0.02414 (19) | |
N | −0.0333 (2) | −0.16912 (19) | 0.03032 (15) | 0.0156 (4) | |
C11 | 0.0379 (3) | −0.2334 (2) | 0.09077 (18) | 0.0172 (5) | |
H11 | 0.1096 | −0.2059 | 0.1244 | 0.021* | |
C12 | −0.0167 (3) | −0.3473 (3) | 0.0926 (2) | 0.0205 (6) | |
H12 | 0.0122 | −0.4070 | 0.1272 | 0.025* | |
C13 | −0.1233 (3) | −0.3528 (2) | 0.03179 (18) | 0.0198 (6) | |
H13 | −0.1775 | −0.4169 | 0.0187 | 0.024* | |
C14 | −0.1321 (3) | −0.2423 (2) | −0.00551 (16) | 0.0171 (6) | |
H14 | −0.1943 | −0.2217 | −0.0475 | 0.020* | |
C21 | −0.2518 (3) | −0.0795 (2) | 0.17301 (17) | 0.0207 (6) | |
H21 | −0.2306 | −0.0031 | 0.1608 | 0.025* | |
C22 | −0.1841 (3) | −0.1491 (3) | 0.23261 (17) | 0.0232 (6) | |
H22 | −0.1098 | −0.1266 | 0.2661 | 0.028* | |
C23 | −0.2485 (3) | −0.2592 (2) | 0.2328 (2) | 0.0234 (7) | |
H23 | −0.2241 | −0.3212 | 0.2666 | 0.028* | |
C24 | −0.3574 (3) | −0.2581 (3) | 0.1722 (2) | 0.0231 (6) | |
H24 | −0.4168 | −0.3191 | 0.1595 | 0.028* | |
C25 | −0.3587 (3) | −0.1468 (2) | 0.13462 (18) | 0.0203 (6) | |
H25 | −0.4186 | −0.1223 | 0.0926 | 0.024* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Pd | 0.01166 (19) | 0.0112 (2) | 0.01351 (19) | −0.00282 (9) | −0.00122 (9) | 0.00050 (9) |
Fe | 0.0128 (2) | 0.0110 (2) | 0.0161 (2) | 0.00033 (13) | 0.00126 (14) | 0.00128 (13) |
Cl | 0.0315 (4) | 0.0178 (3) | 0.0231 (4) | −0.0048 (3) | −0.0134 (3) | 0.0013 (3) |
N | 0.0150 (10) | 0.0145 (11) | 0.0174 (11) | −0.0020 (9) | 0.0012 (9) | 0.0012 (9) |
C11 | 0.0142 (12) | 0.0147 (13) | 0.0226 (14) | 0.0019 (10) | 0.0027 (10) | 0.0037 (11) |
C12 | 0.0189 (13) | 0.0143 (13) | 0.0282 (15) | 0.0033 (10) | 0.0066 (11) | 0.0017 (11) |
C13 | 0.0218 (13) | 0.0146 (13) | 0.0231 (14) | −0.0030 (10) | 0.0081 (11) | −0.0021 (11) |
C14 | 0.0168 (13) | 0.0157 (13) | 0.0187 (13) | −0.0051 (11) | 0.0031 (10) | −0.0023 (10) |
C21 | 0.0215 (13) | 0.0158 (13) | 0.0248 (13) | 0.0034 (11) | 0.0034 (11) | −0.0017 (11) |
C22 | 0.0263 (14) | 0.0249 (15) | 0.0184 (13) | 0.0080 (12) | 0.0008 (11) | −0.0071 (11) |
C23 | 0.0270 (17) | 0.0218 (16) | 0.0214 (14) | 0.0092 (12) | 0.0105 (11) | 0.0057 (11) |
C24 | 0.0205 (14) | 0.0159 (13) | 0.0331 (16) | 0.0007 (11) | 0.0138 (12) | 0.0010 (12) |
C25 | 0.0143 (12) | 0.0195 (13) | 0.0271 (15) | 0.0035 (10) | 0.0018 (10) | 0.0007 (11) |
Geometric parameters (Å, º) top
Pd—Ni | 2.045 (2) | C11—H11 | 0.9300 |
Pd—N | 2.045 (2) | C12—C13 | 1.413 (4) |
Pd—Cli | 2.3057 (9) | C12—H12 | 0.9300 |
Pd—Cl | 2.3057 (9) | C13—C14 | 1.417 (4) |
Fe—N | 2.009 (2) | C13—H13 | 0.9300 |
Fe—C14 | 2.018 (3) | C14—H14 | 0.9300 |
Fe—C11 | 2.023 (3) | C21—C22 | 1.410 (4) |
Fe—C23 | 2.046 (3) | C21—C25 | 1.426 (4) |
Fe—C22 | 2.047 (3) | C21—H21 | 0.9300 |
Fe—C25 | 2.050 (3) | C22—C23 | 1.417 (4) |
Fe—C24 | 2.051 (3) | C22—H22 | 0.9300 |
Fe—C21 | 2.058 (3) | C23—C24 | 1.427 (4) |
Fe—C12 | 2.076 (3) | C23—H23 | 0.9300 |
Fe—C13 | 2.077 (3) | C24—C25 | 1.425 (4) |
N—C14 | 1.394 (4) | C24—H24 | 0.9300 |
N—C11 | 1.401 (4) | C25—H25 | 0.9300 |
C11—C12 | 1.420 (4) | | |
| | | |
Ni—Pd—N | 180.00 (13) | Fe—N—Pd | 124.73 (12) |
Ni—Pd—Cli | 89.58 (7) | N—C11—C12 | 109.2 (3) |
N—Pd—Cli | 90.42 (7) | N—C11—Fe | 69.14 (15) |
Ni—Pd—Cl | 90.42 (7) | C12—C11—Fe | 71.76 (16) |
N—Pd—Cl | 89.58 (7) | N—C11—H11 | 125.4 |
Cli—Pd—Cl | 180.00 (2) | C12—C11—H11 | 125.4 |
N—Fe—C14 | 40.52 (10) | Fe—C11—H11 | 125.3 |
N—Fe—C11 | 40.67 (10) | C13—C12—C11 | 107.1 (3) |
C14—Fe—C11 | 67.58 (12) | C13—C12—Fe | 70.14 (16) |
N—Fe—C23 | 159.37 (12) | C11—C12—Fe | 67.71 (16) |
C14—Fe—C23 | 158.42 (12) | C13—C12—H12 | 126.5 |
C11—Fe—C23 | 123.24 (11) | C11—C12—H12 | 126.5 |
N—Fe—C22 | 122.92 (11) | Fe—C12—H12 | 127.2 |
C14—Fe—C22 | 160.33 (12) | C12—C13—C14 | 107.1 (2) |
C11—Fe—C22 | 106.72 (12) | C12—C13—Fe | 70.07 (16) |
C23—Fe—C22 | 40.50 (12) | C14—C13—Fe | 67.53 (15) |
N—Fe—C25 | 121.82 (11) | C12—C13—H13 | 126.4 |
C14—Fe—C25 | 109.23 (12) | C14—C13—H13 | 126.4 |
C11—Fe—C25 | 156.95 (11) | Fe—C13—H13 | 127.5 |
C23—Fe—C25 | 68.40 (11) | N—C14—C13 | 109.6 (3) |
C22—Fe—C25 | 68.17 (11) | N—C14—Fe | 69.39 (14) |
N—Fe—C24 | 158.02 (11) | C13—C14—Fe | 72.02 (16) |
C14—Fe—C24 | 123.38 (13) | N—C14—H14 | 125.2 |
C11—Fe—C24 | 160.37 (12) | C13—C14—H14 | 125.2 |
C23—Fe—C24 | 40.76 (12) | Fe—C14—H14 | 125.0 |
C22—Fe—C24 | 68.28 (13) | C22—C21—C25 | 108.1 (2) |
C25—Fe—C24 | 40.68 (11) | C22—C21—Fe | 69.48 (15) |
N—Fe—C21 | 107.13 (10) | C25—C21—Fe | 69.36 (16) |
C14—Fe—C21 | 125.18 (12) | C22—C21—H21 | 126.0 |
C11—Fe—C21 | 121.04 (11) | C25—C21—H21 | 126.0 |
C23—Fe—C21 | 67.95 (11) | Fe—C21—H21 | 126.8 |
C22—Fe—C21 | 40.16 (11) | C21—C22—C23 | 108.5 (3) |
C25—Fe—C21 | 40.64 (11) | C21—C22—Fe | 70.35 (16) |
C24—Fe—C21 | 68.21 (11) | C23—C22—Fe | 69.70 (17) |
N—Fe—C12 | 68.52 (11) | C21—C22—H22 | 125.8 |
C14—Fe—C12 | 67.57 (12) | C23—C22—H22 | 125.8 |
C11—Fe—C12 | 40.53 (11) | Fe—C22—H22 | 125.8 |
C23—Fe—C12 | 107.45 (12) | C22—C23—C24 | 108.0 (3) |
C22—Fe—C12 | 121.22 (12) | C22—C23—Fe | 69.79 (16) |
C25—Fe—C12 | 161.46 (11) | C24—C23—Fe | 69.83 (17) |
C24—Fe—C12 | 124.50 (12) | C22—C23—H23 | 126.0 |
C21—Fe—C12 | 156.29 (12) | C24—C23—H23 | 126.0 |
N—Fe—C13 | 68.39 (10) | Fe—C23—H23 | 125.9 |
C14—Fe—C13 | 40.45 (11) | C25—C24—C23 | 107.6 (3) |
C11—Fe—C13 | 67.53 (11) | C25—C24—Fe | 69.60 (16) |
C23—Fe—C13 | 122.31 (11) | C23—C24—Fe | 69.41 (16) |
C22—Fe—C13 | 156.76 (11) | C25—C24—H24 | 126.2 |
C25—Fe—C13 | 125.93 (11) | C23—C24—H24 | 126.2 |
C24—Fe—C13 | 109.12 (12) | Fe—C24—H24 | 126.4 |
C21—Fe—C13 | 162.26 (12) | C24—C25—C21 | 107.8 (3) |
C12—Fe—C13 | 39.80 (12) | C24—C25—Fe | 69.72 (16) |
C14—N—C11 | 107.0 (2) | C21—C25—Fe | 70.00 (16) |
C14—N—Fe | 70.08 (14) | C24—C25—H25 | 126.1 |
C11—N—Fe | 70.20 (15) | C21—C25—H25 | 126.1 |
C14—N—Pd | 126.19 (19) | Fe—C25—H25 | 125.7 |
C11—N—Pd | 126.81 (18) | | |
| | | |
C11—Fe—N—C14 | 117.5 (2) | C13—Fe—C14—N | −119.9 (2) |
C23—Fe—N—C14 | 162.7 (3) | N—Fe—C14—C13 | 119.9 (2) |
C22—Fe—N—C14 | −165.70 (17) | C11—Fe—C14—C13 | 81.17 (18) |
C25—Fe—N—C14 | −82.57 (19) | C23—Fe—C14—C13 | −43.5 (4) |
C24—Fe—N—C14 | −50.5 (3) | C22—Fe—C14—C13 | 157.9 (3) |
C21—Fe—N—C14 | −124.56 (17) | C25—Fe—C14—C13 | −123.28 (18) |
C12—Fe—N—C14 | 80.16 (18) | C24—Fe—C14—C13 | −80.3 (2) |
C13—Fe—N—C14 | 37.23 (17) | C21—Fe—C14—C13 | −165.77 (17) |
C14—Fe—N—C11 | −117.5 (2) | C12—Fe—C14—C13 | 37.17 (17) |
C23—Fe—N—C11 | 45.2 (3) | N—Fe—C21—C22 | −121.09 (17) |
C22—Fe—N—C11 | 76.84 (18) | C14—Fe—C21—C22 | −161.99 (17) |
C25—Fe—N—C11 | 159.97 (16) | C11—Fe—C21—C22 | −78.9 (2) |
C24—Fe—N—C11 | −167.9 (3) | C23—Fe—C21—C22 | 37.62 (18) |
C21—Fe—N—C11 | 117.98 (17) | C25—Fe—C21—C22 | 119.7 (2) |
C12—Fe—N—C11 | −37.30 (16) | C24—Fe—C21—C22 | 81.72 (19) |
C13—Fe—N—C11 | −80.22 (17) | C12—Fe—C21—C22 | −45.6 (4) |
C14—Fe—N—Pd | 120.9 (2) | C13—Fe—C21—C22 | 166.4 (3) |
C11—Fe—N—Pd | −121.7 (2) | N—Fe—C21—C25 | 119.21 (17) |
C23—Fe—N—Pd | −76.5 (3) | C14—Fe—C21—C25 | 78.3 (2) |
C22—Fe—N—Pd | −44.84 (19) | C11—Fe—C21—C25 | 161.41 (16) |
C25—Fe—N—Pd | 38.29 (19) | C23—Fe—C21—C25 | −82.07 (18) |
C24—Fe—N—Pd | 70.4 (3) | C22—Fe—C21—C25 | −119.7 (2) |
C21—Fe—N—Pd | −3.70 (17) | C24—Fe—C21—C25 | −37.98 (17) |
C12—Fe—N—Pd | −158.98 (18) | C12—Fe—C21—C25 | −165.3 (3) |
C13—Fe—N—Pd | 158.10 (17) | C13—Fe—C21—C25 | 46.7 (4) |
Cli—Pd—N—C14 | −11.4 (2) | C25—C21—C22—C23 | −0.7 (3) |
Cl—Pd—N—C14 | 168.6 (2) | Fe—C21—C22—C23 | −59.49 (19) |
Cli—Pd—N—C11 | 168.7 (2) | C25—C21—C22—Fe | 58.78 (19) |
Cl—Pd—N—C11 | −11.3 (2) | N—Fe—C22—C21 | 77.12 (19) |
Cli—Pd—N—Fe | −101.06 (13) | C14—Fe—C22—C21 | 48.7 (4) |
Cl—Pd—N—Fe | 78.94 (13) | C11—Fe—C22—C21 | 118.61 (17) |
C14—N—C11—C12 | 0.1 (3) | C23—Fe—C22—C21 | −119.4 (2) |
Fe—N—C11—C12 | 60.80 (19) | C25—Fe—C22—C21 | −37.55 (17) |
Pd—N—C11—C12 | 179.93 (18) | C24—Fe—C22—C21 | −81.51 (18) |
C14—N—C11—Fe | −60.74 (18) | C12—Fe—C22—C21 | 160.37 (17) |
Pd—N—C11—Fe | 119.13 (19) | C13—Fe—C22—C21 | −169.6 (3) |
C14—Fe—C11—N | 38.59 (15) | N—Fe—C22—C23 | −163.47 (16) |
C23—Fe—C11—N | −162.61 (15) | C14—Fe—C22—C23 | 168.1 (3) |
C22—Fe—C11—N | −121.41 (16) | C11—Fe—C22—C23 | −121.98 (17) |
C25—Fe—C11—N | −48.0 (4) | C25—Fe—C22—C23 | 81.86 (18) |
C24—Fe—C11—N | 166.5 (3) | C24—Fe—C22—C23 | 37.90 (17) |
C21—Fe—C11—N | −80.04 (18) | C21—Fe—C22—C23 | 119.4 (2) |
C12—Fe—C11—N | 119.8 (2) | C12—Fe—C22—C23 | −80.23 (19) |
C13—Fe—C11—N | 82.52 (17) | C13—Fe—C22—C23 | −50.2 (3) |
N—Fe—C11—C12 | −119.8 (2) | C21—C22—C23—C24 | 0.3 (3) |
C14—Fe—C11—C12 | −81.21 (19) | Fe—C22—C23—C24 | −59.6 (2) |
C23—Fe—C11—C12 | 77.6 (2) | C21—C22—C23—Fe | 59.89 (19) |
C22—Fe—C11—C12 | 118.79 (19) | N—Fe—C23—C22 | 42.7 (4) |
C25—Fe—C11—C12 | −167.8 (3) | C14—Fe—C23—C22 | −169.1 (3) |
C24—Fe—C11—C12 | 46.7 (4) | C11—Fe—C23—C22 | 76.24 (19) |
C21—Fe—C11—C12 | 160.16 (17) | C25—Fe—C23—C22 | −81.24 (17) |
C13—Fe—C11—C12 | −37.28 (18) | C24—Fe—C23—C22 | −119.1 (2) |
N—C11—C12—C13 | 0.2 (3) | C21—Fe—C23—C22 | −37.32 (16) |
Fe—C11—C12—C13 | 59.34 (19) | C12—Fe—C23—C22 | 117.94 (17) |
N—C11—C12—Fe | −59.19 (18) | C13—Fe—C23—C22 | 158.99 (16) |
N—Fe—C12—C13 | −81.60 (17) | N—Fe—C23—C24 | 161.7 (3) |
C14—Fe—C12—C13 | −37.76 (17) | C14—Fe—C23—C24 | −50.0 (4) |
C11—Fe—C12—C13 | −119.0 (2) | C11—Fe—C23—C24 | −164.70 (16) |
C23—Fe—C12—C13 | 119.87 (18) | C22—Fe—C23—C24 | 119.1 (2) |
C22—Fe—C12—C13 | 162.01 (16) | C25—Fe—C23—C24 | 37.81 (17) |
C25—Fe—C12—C13 | 45.9 (4) | C21—Fe—C23—C24 | 81.74 (18) |
C24—Fe—C12—C13 | 78.2 (2) | C12—Fe—C23—C24 | −123.00 (17) |
C21—Fe—C12—C13 | −165.4 (2) | C13—Fe—C23—C24 | −81.95 (19) |
N—Fe—C12—C11 | 37.42 (16) | C22—C23—C24—C25 | 0.3 (3) |
C14—Fe—C12—C11 | 81.26 (18) | Fe—C23—C24—C25 | −59.33 (19) |
C23—Fe—C12—C11 | −121.10 (18) | C22—C23—C24—Fe | 59.6 (2) |
C22—Fe—C12—C11 | −79.0 (2) | N—Fe—C24—C25 | −43.8 (4) |
C25—Fe—C12—C11 | 164.9 (3) | C14—Fe—C24—C25 | −80.7 (2) |
C24—Fe—C12—C11 | −162.74 (18) | C11—Fe—C24—C25 | 160.1 (3) |
C21—Fe—C12—C11 | −46.3 (4) | C23—Fe—C24—C25 | 119.0 (2) |
C13—Fe—C12—C11 | 119.0 (2) | C22—Fe—C24—C25 | 81.34 (19) |
C11—C12—C13—C14 | −0.3 (3) | C21—Fe—C24—C25 | 37.94 (17) |
Fe—C12—C13—C14 | 57.51 (19) | C12—Fe—C24—C25 | −164.88 (17) |
C11—C12—C13—Fe | −57.81 (19) | C13—Fe—C24—C25 | −123.33 (18) |
N—Fe—C13—C12 | 81.97 (18) | N—Fe—C24—C23 | −162.8 (3) |
C14—Fe—C13—C12 | 119.3 (2) | C14—Fe—C24—C23 | 160.27 (17) |
C11—Fe—C13—C12 | 37.94 (17) | C11—Fe—C24—C23 | 41.1 (4) |
C23—Fe—C13—C12 | −78.2 (2) | C22—Fe—C24—C23 | −37.67 (17) |
C22—Fe—C13—C12 | −42.0 (4) | C25—Fe—C24—C23 | −119.0 (2) |
C25—Fe—C13—C12 | −163.62 (17) | C21—Fe—C24—C23 | −81.07 (18) |
C24—Fe—C13—C12 | −121.35 (18) | C12—Fe—C24—C23 | 76.1 (2) |
C21—Fe—C13—C12 | 160.5 (3) | C13—Fe—C24—C23 | 117.66 (18) |
N—Fe—C13—C14 | −37.30 (17) | C23—C24—C25—C21 | −0.7 (3) |
C11—Fe—C13—C14 | −81.32 (18) | Fe—C24—C25—C21 | −59.91 (19) |
C23—Fe—C13—C14 | 162.56 (17) | C23—C24—C25—Fe | 59.21 (19) |
C22—Fe—C13—C14 | −161.3 (3) | C22—C21—C25—C24 | 0.9 (3) |
C25—Fe—C13—C14 | 77.1 (2) | Fe—C21—C25—C24 | 59.73 (19) |
C24—Fe—C13—C14 | 119.39 (19) | C22—C21—C25—Fe | −58.86 (19) |
C21—Fe—C13—C14 | 41.3 (4) | N—Fe—C25—C24 | 162.24 (17) |
C12—Fe—C13—C14 | −119.3 (2) | C14—Fe—C25—C24 | 119.21 (19) |
C11—N—C14—C13 | −0.3 (3) | C11—Fe—C25—C24 | −163.0 (3) |
Fe—N—C14—C13 | −61.07 (19) | C23—Fe—C25—C24 | −37.88 (18) |
Pd—N—C14—C13 | 179.87 (18) | C22—Fe—C25—C24 | −81.6 (2) |
C11—N—C14—Fe | 60.81 (18) | C21—Fe—C25—C24 | −118.8 (2) |
Pd—N—C14—Fe | −119.06 (19) | C12—Fe—C25—C24 | 42.6 (4) |
C12—C13—C14—N | 0.4 (3) | C13—Fe—C25—C24 | 77.1 (2) |
Fe—C13—C14—N | 59.46 (19) | N—Fe—C25—C21 | −79.00 (18) |
C12—C13—C14—Fe | −59.1 (2) | C14—Fe—C25—C21 | −122.04 (17) |
C11—Fe—C14—N | −38.72 (15) | C11—Fe—C25—C21 | −44.3 (4) |
C23—Fe—C14—N | −163.4 (3) | C23—Fe—C25—C21 | 80.87 (18) |
C22—Fe—C14—N | 38.0 (4) | C22—Fe—C25—C21 | 37.12 (17) |
C25—Fe—C14—N | 116.83 (17) | C24—Fe—C25—C21 | 118.8 (2) |
C24—Fe—C14—N | 159.77 (15) | C12—Fe—C25—C21 | 161.3 (3) |
C21—Fe—C14—N | 74.34 (19) | C13—Fe—C25—C21 | −164.10 (16) |
C12—Fe—C14—N | −82.73 (17) | | |
Symmetry code: (i) −x, −y, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C23—H23···Clii | 0.93 | 2.76 | 3.678 (3) | 171 |
Symmetry code: (ii) −x, y−1/2, −z+1/2. |