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Acta Cryst. (2007). E63, m1790    [ doi:10.1107/S1600536807021915 ]

Tetraethylammonium dichlorido[N,N'-(4,5-dichloro-o-phenylene)bis(4-tert-butylpyridine-2-carboxamide)-[kappa]4N]ferrate(III) acetonitrile solvate

X.-B. Xu, L. Yang, Y.-Y. Qu, L.-X. Li and X.-G. Zhou

Abstract top

In the title compound, (C8H20N)[Fe(C26H26Cl2N4O2)Cl2]·CHCl3, conventionally abbreviated as [NEt4][Fe(bbpc)Cl2]·CHCl3 [H2bbpc = N,N'-(4,5-dichloro-o-phenylene)bis(4-tert-butylpyridine-2-carboxamide)], the FeIII ion is six-coordinate, forming a distorted octahedron with two pyridine and two deprotonated amide N atoms in the equatorial plane, while the two axial sites are occupied by two Cl atoms.

Comment top

There has been a growing interest in the coordination chemistry of peptide complexes of iron in a +3 or higher oxidation state (Marlin et al., 1999; Che et al., 1992). Mascharak and Collins have provided examples of structurally characterized complexes with coordinated carboxamido N atoms as a part of macrocyclic and nonmacrocyclic ligand framework, while high valent iron species have been proposed on the basis of catalytic studies for a variety of oxidation systems (Marlin et al., 1999; Collins et al., 1992; Bartos et al., 1995). As part of our studies on catalysis by N4 non-porphyrin complexes (Liu et al., 2006; Yan et al., 2006), we report here the synthesis and structures of the ironIII complex with 1,2-bis(4'-tert-butylpyridine-2'-carboxamido)-4,5-dichlorobenzene (H2bbpc).

In the title compound, the ironIII ion is six-coordinated forming a distorted octahedron. Two pyridine and two deprotonated amide nitrogen atoms of the ligand are in the equatorial plane whereas the two axial sites are occupied by Cl atoms (Fig. 1) as usually observed with a Cl(1)—Fe(1)—Cl(2) angle of 151.33°, which is similar to 152.3° of [Et3NH][Fe(III)(bpb)Cl2] (Yang et al., 1991). The Fe—N(amide) and Fe—N(pyridine) distances at 2.0455 (19) Å and 2.170 (2) Å are also comparable to those of [Et3NH][Fe(III)(bpb)Cl2] (Yang et al., 1991) and [Fe(III)(bpc)Cl(DMF)] (Patra et al., 1999).

Related literature top

For related literature, see: Bartos et al. (1995); Che et al. (1992); Collins et al. (1992); Liu et al. (2006); Marlin et al. (1999); Patra & Mukherjee (1999); Ray et al. (1993); Yan et al. (2006); Yang et al. (1991).

Experimental top

The ironIII complex [NEt4][Fe(bbpc)Cl2] was prepared according to the literature (Ray et al., 1993). Single crystals suitable for X-ray analysis were obtained by slow diffusion of ether into chloroform solution. Selected IR data (KBr, cm-1): 2968 (m), 1626 (amide I band, s), 1596 (amide II band, s), 1375 (s), 1171 (m), 957 (m), 853 (m). Anal calculated for C34H46Cl4N5O2Fe: C, 54.13; H, 6.15; N, 9.28. Found: C, 53.87; H, 6.36; N, 9.05. MS (FAB): 624 ([Fe(bbpc)Cl2]+).

Refinement top

All H atoms were fixed geometrically and treated as riding on their parent C atoms with C—H = 0.93 Å (aromatic), 0.97 Å (methylene) and 0.96Å (methyl) with Uiso(H) = 1.2Ueq(aromatic, methylene) or Uiso(H) = 1.5Ueq(methyl). One of the tertiobutyl group is disordered over two positions with occupancy in the ratio 0.39/0.61. This disorder was treated applying restraints to keep a reasonable chemical structure. The Cl atoms in the solvent molecule present large ellipsoids components but any attempts to modelize a reasonable model failed.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1998); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. A view of compound (I) including the complex anion and the cation. The chlrophorm solvent molecule and the H atoms were omitted for clarity. Displacement ellipsoids are drawn at the 30% propability level.
Tetraethylammonium dichlorido[N,N'-(4,5-dichloro-o-phenylene)bis(4-tert- butylpyridine-2-carboxamide)-κ4N]iron(III) acetonitrile solvate top
Crystal data top
(C8H20N)[Fe(C26H26Cl2N4O2)Cl2]·CHCl3F000 = 1812
Mr = 873.78Dx = 1.372 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 8783 reflections
a = 11.1740 (17) Åθ = 1–27.5º
b = 26.598 (4) ŵ = 0.84 mm−1
c = 15.000 (2) ÅT = 294 (2) K
β = 108.380 (3)ºNeedle, green
V = 4230.9 (11) Å30.38 × 0.16 × 0.12 mm
Z = 4
Data collection top
Bruker CCD area-detector
diffractometer		9757 independent reflections
Radiation source: fine-focus sealed tube4586 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.082
T = 294(2) Kθmax = 27.6º
φ and ω scansh = −14→14
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		k = −34→24
Tmin = 0.742, Tmax = 0.906l = −19→19
28612 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.064H-atom parameters constrained
wR(F2) = 0.202  w = 1/[σ2(Fo2) + (0.0902P)2 + 1.0929P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
9757 reflectionsΔρmax = 0.82 e Å−3
461 parametersΔρmin = −0.72 e Å−3
6 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
(C8H20N)[Fe(C26H26Cl2N4O2)Cl2]·CHCl3V = 4230.9 (11) Å3
Mr = 873.78Z = 4
Monoclinic, P21/cMo Kα
a = 11.1740 (17) ŵ = 0.84 mm−1
b = 26.598 (4) ÅT = 294 (2) K
c = 15.000 (2) Å0.38 × 0.16 × 0.12 mm
β = 108.380 (3)º
Data collection top
Bruker CCD area-detector
diffractometer		9757 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		4586 reflections with I > 2σ(I)
Tmin = 0.742, Tmax = 0.906Rint = 0.082
28612 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0646 restraints
wR(F2) = 0.202H-atom parameters constrained
S = 1.01Δρmax = 0.82 e Å−3
9757 reflectionsΔρmin = −0.72 e Å−3
461 parameters
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
xyzUiso*/UeqOcc. (<1)
Fe10.51046 (6)0.68484 (2)0.42776 (4)0.03555 (19)
Cl10.69772 (11)0.66071 (5)0.40275 (9)0.0552 (3)
Cl20.33154 (12)0.73891 (5)0.39800 (10)0.0592 (4)
Cl30.39772 (15)0.47520 (5)0.66487 (10)0.0738 (4)
Cl40.56072 (17)0.54520 (5)0.82960 (9)0.0791 (5)
O10.2920 (4)0.55604 (14)0.3533 (2)0.0769 (12)
O20.6434 (4)0.71324 (13)0.7157 (2)0.0691 (11)
N10.4310 (3)0.61699 (13)0.4378 (2)0.0403 (9)
N20.4232 (3)0.66324 (13)0.2817 (2)0.0384 (8)
N30.5568 (3)0.67498 (12)0.5709 (2)0.0394 (9)
N40.6103 (3)0.75347 (13)0.4854 (2)0.0389 (9)
C10.4538 (4)0.59680 (16)0.5284 (3)0.0392 (10)
C20.4177 (5)0.54949 (17)0.5499 (3)0.0486 (12)
H20.37160.52840.50190.058*
C30.4497 (5)0.53371 (17)0.6416 (3)0.0469 (12)
C40.5199 (5)0.56432 (17)0.7140 (3)0.0494 (12)
C50.5564 (5)0.61223 (16)0.6936 (3)0.0455 (11)
H50.60240.63310.74210.055*
C60.5243 (4)0.62872 (15)0.6015 (3)0.0377 (10)
C70.3580 (5)0.59411 (18)0.3598 (3)0.0487 (12)
C80.3598 (4)0.61986 (16)0.2707 (3)0.0403 (11)
C90.3016 (5)0.59894 (18)0.1842 (3)0.0491 (12)
H90.25680.56910.18000.059*
C100.3088 (4)0.62196 (17)0.1025 (3)0.0460 (11)
C110.3735 (5)0.66710 (18)0.1158 (3)0.0504 (12)
H110.37910.68470.06380.060*
C120.4295 (4)0.68648 (18)0.2039 (3)0.0456 (11)
H120.47330.71670.20990.055*
C130.2490 (5)0.59941 (19)0.0053 (3)0.0570 (13)
C140.1764 (6)0.5507 (2)0.0082 (4)0.083 (2)
H14A0.14230.5374−0.05420.124*
H14B0.10900.55770.03320.124*
H14C0.23260.52650.04740.124*
C150.1525 (6)0.6372 (2)−0.0550 (4)0.0752 (17)
H15A0.10970.6225−0.11500.113*
H15B0.19550.6671−0.06380.113*
H15C0.09220.6455−0.02380.113*
C160.3521 (6)0.5890 (3)−0.0374 (5)0.110 (3)
H16A0.40690.5633−0.00190.166*
H16B0.39970.6192−0.03640.166*
H16C0.31530.5780−0.10110.166*
C170.6155 (4)0.71209 (16)0.6296 (3)0.0424 (11)
C180.6447 (4)0.75677 (15)0.5787 (3)0.0384 (10)
C190.7036 (4)0.79860 (16)0.6265 (3)0.0416 (11)
H190.72530.79960.69170.050*
C200.7311 (4)0.83949 (16)0.5783 (3)0.0405 (10)
C210.6945 (5)0.83492 (18)0.4817 (3)0.0506 (12)
H210.71030.86120.44600.061*
C220.6354 (5)0.79231 (17)0.4377 (3)0.0500 (12)
H220.61210.79040.37250.060*
C230.7961 (5)0.88641 (18)0.6282 (3)0.0519 (13)
C24A0.9179 (14)0.8686 (6)0.7044 (11)0.0870 (19)0.39
H24A0.97330.85320.67480.131*0.39
H24B0.89660.84460.74480.131*0.39
H24C0.95930.89690.74090.131*0.39
C25A0.7102 (15)0.9105 (6)0.6776 (12)0.0870 (19)0.39
H25A0.71300.89120.73220.131*0.39
H25B0.62530.91140.63550.131*0.39
H25C0.73830.94420.69600.131*0.39
C26A0.8306 (18)0.9228 (6)0.5640 (11)0.0870 (19)0.39
H26A0.87340.90520.52710.131*0.39
H26B0.88490.94830.60070.131*0.39
H26C0.75540.93810.52320.131*0.39
C24B0.8573 (12)0.8799 (4)0.7337 (6)0.0870 (19)0.61
H24D0.91550.90690.75760.131*0.61
H24E0.90160.84840.74590.131*0.61
H24F0.79340.88020.76400.131*0.61
C25B0.6950 (10)0.9287 (4)0.6160 (8)0.0870 (19)0.61
H25D0.73330.95760.65240.131*0.61
H25E0.62770.91670.63720.131*0.61
H25F0.66210.93790.55090.131*0.61
C26B0.8916 (10)0.9059 (4)0.5842 (8)0.0870 (19)0.61
H26D0.85130.91110.51820.131*0.61
H26E0.95840.88180.59330.131*0.61
H26F0.92580.93710.61330.131*0.61
N51.0897 (4)0.69071 (17)0.5774 (3)0.0616 (12)
C271.0491 (7)0.6444 (3)0.5164 (6)0.098 (2)
H27A1.05200.61560.55680.117*
H27B0.96220.64880.47730.117*
C281.1258 (8)0.6334 (4)0.4559 (6)0.139 (3)
H28A1.21260.63010.49370.208*
H28B1.11780.66040.41180.208*
H28C1.09760.60260.42250.208*
C291.2224 (6)0.6877 (3)0.6422 (5)0.093 (2)
H29A1.27850.68600.60440.112*
H29B1.24130.71870.67820.112*
C301.2517 (8)0.6448 (3)0.7091 (6)0.125 (3)
H30A1.23130.61390.67480.188*
H30B1.20290.64770.75130.188*
H30C1.33990.64520.74440.188*
C310.9954 (6)0.6931 (3)0.6309 (6)0.108 (3)
H31A0.91150.69510.58570.129*
H31B1.00040.66180.66520.129*
C321.0105 (10)0.7346 (5)0.6971 (8)0.196 (6)
H32A0.93160.74100.70790.294*
H32B1.03670.76420.67160.294*
H32C1.07310.72600.75540.294*
C331.0820 (6)0.7370 (3)0.5178 (5)0.094 (2)
H33A1.10560.76580.55920.112*
H33B1.14380.73390.48510.112*
C340.9560 (7)0.7475 (3)0.4466 (6)0.118 (3)
H34A0.89350.75110.47780.177*
H34B0.93310.72020.40270.177*
H34C0.96060.77800.41360.177*
Cl110.19736 (18)0.43278 (9)0.41748 (17)0.1219 (8)
C35A0.1169 (9)0.4704 (3)0.3228 (7)0.162 (5)
H35A0.16030.50280.32770.194*
Cl2A−0.0355 (3)0.48061 (12)0.3158 (4)0.248 (2)
Cl3A0.1157 (4)0.4405 (2)0.2175 (3)0.271 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0450 (4)0.0311 (3)0.0310 (3)−0.0062 (3)0.0126 (3)−0.0013 (3)
Cl10.0479 (7)0.0577 (8)0.0614 (8)−0.0011 (6)0.0194 (6)−0.0077 (6)
Cl20.0567 (8)0.0543 (8)0.0667 (9)0.0088 (6)0.0197 (7)−0.0022 (6)
Cl30.1042 (12)0.0443 (8)0.0731 (10)−0.0178 (7)0.0286 (9)0.0186 (7)
Cl40.1320 (14)0.0584 (9)0.0447 (8)−0.0082 (8)0.0248 (9)0.0152 (6)
O10.109 (3)0.065 (2)0.050 (2)−0.056 (2)0.016 (2)−0.0018 (18)
O20.128 (3)0.048 (2)0.0294 (18)−0.022 (2)0.021 (2)−0.0039 (15)
N10.048 (2)0.038 (2)0.033 (2)−0.0066 (17)0.0103 (17)0.0019 (16)
N20.043 (2)0.039 (2)0.034 (2)−0.0063 (17)0.0134 (17)−0.0026 (16)
N30.052 (2)0.030 (2)0.038 (2)−0.0045 (16)0.0169 (18)−0.0001 (15)
N40.052 (2)0.035 (2)0.0294 (19)−0.0059 (16)0.0126 (17)0.0005 (15)
C10.047 (3)0.035 (2)0.037 (2)−0.001 (2)0.016 (2)0.002 (2)
C20.064 (3)0.039 (3)0.044 (3)−0.011 (2)0.019 (2)0.002 (2)
C30.060 (3)0.033 (3)0.052 (3)−0.005 (2)0.024 (3)0.006 (2)
C40.071 (3)0.038 (3)0.042 (3)0.009 (2)0.023 (3)0.010 (2)
C50.065 (3)0.034 (3)0.038 (3)−0.003 (2)0.017 (2)0.001 (2)
C60.048 (3)0.029 (2)0.040 (2)0.0003 (19)0.019 (2)0.0040 (19)
C70.057 (3)0.045 (3)0.044 (3)−0.020 (2)0.015 (2)−0.005 (2)
C80.046 (3)0.036 (3)0.037 (2)−0.008 (2)0.010 (2)0.0014 (19)
C90.060 (3)0.042 (3)0.042 (3)−0.015 (2)0.012 (2)−0.006 (2)
C100.053 (3)0.044 (3)0.038 (3)0.001 (2)0.010 (2)−0.003 (2)
C110.065 (3)0.048 (3)0.036 (3)−0.006 (2)0.014 (2)0.003 (2)
C120.052 (3)0.045 (3)0.038 (3)−0.013 (2)0.012 (2)0.002 (2)
C130.070 (4)0.053 (3)0.039 (3)0.004 (3)0.005 (3)−0.008 (2)
C140.120 (5)0.049 (4)0.055 (4)−0.005 (3)−0.007 (3)−0.006 (3)
C150.091 (4)0.067 (4)0.051 (3)−0.007 (3)−0.002 (3)−0.001 (3)
C160.094 (5)0.171 (8)0.068 (4)0.013 (5)0.029 (4)−0.047 (5)
C170.058 (3)0.035 (3)0.035 (3)−0.004 (2)0.015 (2)−0.004 (2)
C180.048 (3)0.033 (2)0.033 (2)−0.0030 (19)0.012 (2)0.0000 (19)
C190.054 (3)0.038 (3)0.033 (2)−0.002 (2)0.014 (2)−0.0028 (19)
C200.049 (3)0.030 (2)0.043 (3)−0.0030 (19)0.014 (2)−0.002 (2)
C210.072 (3)0.038 (3)0.042 (3)−0.017 (2)0.018 (2)0.001 (2)
C220.074 (3)0.043 (3)0.032 (2)−0.015 (2)0.015 (2)0.001 (2)
C230.066 (3)0.040 (3)0.050 (3)−0.017 (2)0.019 (3)−0.004 (2)
C24A0.117 (5)0.056 (4)0.085 (4)−0.029 (3)0.027 (4)−0.025 (3)
C25A0.117 (5)0.056 (4)0.085 (4)−0.029 (3)0.027 (4)−0.025 (3)
C26A0.117 (5)0.056 (4)0.085 (4)−0.029 (3)0.027 (4)−0.025 (3)
C24B0.117 (5)0.056 (4)0.085 (4)−0.029 (3)0.027 (4)−0.025 (3)
C25B0.117 (5)0.056 (4)0.085 (4)−0.029 (3)0.027 (4)−0.025 (3)
C26B0.117 (5)0.056 (4)0.085 (4)−0.029 (3)0.027 (4)−0.025 (3)
N50.052 (3)0.065 (3)0.068 (3)−0.004 (2)0.020 (2)0.002 (2)
C270.077 (5)0.086 (5)0.122 (6)−0.009 (4)0.020 (5)0.009 (5)
C280.107 (6)0.184 (9)0.121 (7)0.043 (6)0.030 (6)−0.041 (6)
C290.067 (4)0.111 (6)0.099 (5)0.012 (4)0.023 (4)0.001 (4)
C300.111 (6)0.156 (8)0.107 (6)0.049 (6)0.030 (5)0.034 (6)
C310.073 (5)0.147 (8)0.108 (6)0.016 (5)0.035 (5)0.013 (5)
C320.133 (9)0.295 (16)0.146 (9)0.091 (9)0.024 (7)−0.072 (10)
C330.081 (5)0.080 (5)0.117 (6)−0.013 (4)0.026 (4)0.016 (4)
C340.089 (5)0.107 (6)0.135 (7)−0.014 (4)0.001 (5)0.051 (5)
Cl110.0844 (13)0.1178 (17)0.1413 (19)−0.0121 (11)0.0038 (12)0.0392 (14)
C35A0.135 (8)0.128 (7)0.158 (9)−0.092 (6)−0.047 (6)0.059 (6)
Cl2A0.136 (2)0.145 (3)0.414 (6)0.027 (2)0.017 (3)0.137 (3)
Cl3A0.187 (4)0.410 (7)0.150 (3)−0.071 (4)−0.040 (3)−0.039 (4)
Geometric parameters (Å, °) top
Fe1—N12.038 (3)C23—C26A1.498 (13)
Fe1—N32.060 (3)C23—C26B1.512 (10)
Fe1—N42.172 (3)C23—C24B1.522 (10)
Fe1—N22.176 (3)C23—C25A1.526 (13)
Fe1—Cl12.3294 (14)C23—C24A1.550 (13)
Fe1—Cl22.3879 (14)C23—C25B1.564 (10)
Cl3—C31.735 (5)C24A—H24A0.9600
Cl4—C41.724 (5)C24A—H24B0.9600
O1—C71.238 (5)C24A—H24C0.9600
O2—C171.231 (5)C25A—H25A0.9600
N1—C71.342 (5)C25A—H25B0.9600
N1—C11.407 (5)C25A—H25C0.9600
N2—C81.337 (5)C26A—H26A0.9600
N2—C121.342 (5)C26A—H26B0.9600
N3—C171.347 (5)C26A—H26C0.9600
N3—C61.401 (5)C24B—H24D0.9600
N4—C181.331 (5)C24B—H24E0.9600
N4—C221.336 (5)C24B—H24F0.9600
C1—C21.390 (6)C25B—H25D0.9600
C1—C61.415 (6)C25B—H25E0.9600
C2—C31.373 (6)C25B—H25F0.9600
C2—H20.9300C26B—H26D0.9600
C3—C41.387 (7)C26B—H26E0.9600
C4—C51.401 (6)C26B—H26F0.9600
C5—C61.384 (6)N5—C291.497 (7)
C5—H50.9300N5—C331.508 (7)
C7—C81.507 (6)N5—C311.513 (8)
C8—C91.374 (6)N5—C271.516 (8)
C9—C101.394 (6)C27—C281.461 (10)
C9—H90.9300C27—H27A0.9700
C10—C111.383 (6)C27—H27B0.9700
C10—C131.523 (6)C28—H28A0.9600
C11—C121.372 (6)C28—H28B0.9600
C11—H110.9300C28—H28C0.9600
C12—H120.9300C29—C301.485 (9)
C13—C161.510 (8)C29—H29A0.9700
C13—C141.537 (7)C29—H29B0.9700
C13—C151.542 (7)C30—H30A0.9600
C14—H14A0.9600C30—H30B0.9600
C14—H14B0.9600C30—H30C0.9600
C14—H14C0.9600C31—C321.459 (11)
C15—H15A0.9600C31—H31A0.9700
C15—H15B0.9600C31—H31B0.9700
C15—H15C0.9600C32—H32A0.9600
C16—H16A0.9600C32—H32B0.9600
C16—H16B0.9600C32—H32C0.9600
C16—H16C0.9600C33—C341.502 (9)
C17—C181.503 (6)C33—H33A0.9700
C18—C191.374 (6)C33—H33B0.9700
C19—C201.393 (6)C34—H34A0.9600
C19—H190.9300C34—H34B0.9600
C20—C211.381 (6)C34—H34C0.9600
C20—C231.517 (6)Cl11—C35A1.738 (8)
C21—C221.372 (6)C35A—Cl2A1.694 (11)
C21—H210.9300C35A—Cl3A1.764 (12)
C22—H220.9300C35A—H35A0.9800
N1—Fe1—N377.44 (13)C26B—C23—C20111.1 (5)
N1—Fe1—N4153.65 (13)C26A—C23—C24B128.2 (9)
N3—Fe1—N476.30 (13)C26B—C23—C24B110.2 (7)
N1—Fe1—N276.90 (13)C20—C23—C24B114.0 (5)
N3—Fe1—N2154.33 (14)C26A—C23—C25A111.6 (10)
N4—Fe1—N2129.33 (13)C26B—C23—C25A134.9 (8)
N1—Fe1—Cl1101.69 (11)C20—C23—C25A107.9 (7)
N3—Fe1—Cl1100.91 (11)C24B—C23—C25A71.9 (9)
N4—Fe1—Cl185.46 (10)C26A—C23—C24A109.1 (10)
N2—Fe1—Cl184.56 (10)C26B—C23—C24A81.4 (9)
N1—Fe1—Cl2100.86 (11)C20—C23—C24A106.5 (7)
N3—Fe1—Cl2101.07 (11)C24B—C23—C24A36.6 (7)
N4—Fe1—Cl282.12 (10)C25A—C23—C24A108.1 (10)
N2—Fe1—Cl283.56 (10)C26A—C23—C25B77.4 (9)
Cl1—Fe1—Cl2151.34 (5)C26B—C23—C25B106.6 (7)
C7—N1—C1122.9 (4)C20—C23—C25B108.6 (5)
C7—N1—Fe1119.8 (3)C24B—C23—C25B105.9 (7)
C1—N1—Fe1117.3 (3)C25A—C23—C25B38.1 (7)
C8—N2—C12117.5 (4)C24A—C23—C25B137.7 (8)
C8—N2—Fe1113.8 (3)C23—C24A—H24A109.5
C12—N2—Fe1128.6 (3)C23—C24A—H24B109.5
C17—N3—C6123.5 (4)C23—C24A—H24C109.5
C17—N3—Fe1119.9 (3)C23—C25A—H25A109.5
C6—N3—Fe1116.6 (3)C23—C25A—H25B109.5
C18—N4—C22118.2 (4)C23—C25A—H25C109.5
C18—N4—Fe1114.6 (3)C23—C26A—H26A109.5
C22—N4—Fe1127.2 (3)C23—C26A—H26B109.5
C2—C1—N1126.3 (4)C23—C26A—H26C109.5
C2—C1—C6119.7 (4)C23—C24B—H24D109.5
N1—C1—C6114.0 (4)C23—C24B—H24E109.5
C3—C2—C1120.4 (4)H24D—C24B—H24E109.5
C3—C2—H2119.8C23—C24B—H24F109.5
C1—C2—H2119.8H24D—C24B—H24F109.5
C2—C3—C4120.7 (4)H24E—C24B—H24F109.5
C2—C3—Cl3118.6 (4)C23—C25B—H25D109.5
C4—C3—Cl3120.7 (4)C23—C25B—H25E109.5
C3—C4—C5119.6 (4)H25D—C25B—H25E109.5
C3—C4—Cl4121.3 (4)C23—C25B—H25F109.5
C5—C4—Cl4119.1 (4)H25D—C25B—H25F109.5
C6—C5—C4120.4 (4)H25E—C25B—H25F109.5
C6—C5—H5119.8C23—C26B—H26D109.5
C4—C5—H5119.8C23—C26B—H26E109.5
C5—C6—N3126.4 (4)H26D—C26B—H26E109.5
C5—C6—C1119.3 (4)C23—C26B—H26F109.5
N3—C6—C1114.3 (4)H26D—C26B—H26F109.5
O1—C7—N1128.5 (4)H26E—C26B—H26F109.5
O1—C7—C8118.4 (4)C29—N5—C33106.8 (5)
N1—C7—C8113.1 (4)C29—N5—C31111.8 (5)
N2—C8—C9122.7 (4)C33—N5—C31111.1 (5)
N2—C8—C7116.0 (4)C29—N5—C27113.3 (5)
C9—C8—C7121.3 (4)C33—N5—C27110.8 (5)
C8—C9—C10120.8 (4)C31—N5—C27103.2 (5)
C8—C9—H9119.6C28—C27—N5114.5 (6)
C10—C9—H9119.6C28—C27—H27A108.6
C11—C10—C9115.3 (4)N5—C27—H27A108.6
C11—C10—C13122.1 (4)C28—C27—H27B108.6
C9—C10—C13122.6 (4)N5—C27—H27B108.6
C12—C11—C10121.7 (4)H27A—C27—H27B107.6
C12—C11—H11119.2C27—C28—H28A109.5
C10—C11—H11119.2C27—C28—H28B109.5
N2—C12—C11122.0 (4)H28A—C28—H28B109.5
N2—C12—H12119.0C27—C28—H28C109.5
C11—C12—H12119.0H28A—C28—H28C109.5
C16—C13—C10108.4 (5)H28B—C28—H28C109.5
C16—C13—C14109.7 (5)C30—C29—N5116.2 (6)
C10—C13—C14112.4 (4)C30—C29—H29A108.2
C16—C13—C15110.9 (5)N5—C29—H29A108.2
C10—C13—C15108.6 (4)C30—C29—H29B108.2
C14—C13—C15106.8 (5)N5—C29—H29B108.2
C13—C14—H14A109.5H29A—C29—H29B107.4
C13—C14—H14B109.5C29—C30—H30A109.5
H14A—C14—H14B109.5C29—C30—H30B109.5
C13—C14—H14C109.5H30A—C30—H30B109.5
H14A—C14—H14C109.5C29—C30—H30C109.5
H14B—C14—H14C109.5H30A—C30—H30C109.5
C13—C15—H15A109.5H30B—C30—H30C109.5
C13—C15—H15B109.5C32—C31—N5116.3 (8)
H15A—C15—H15B109.5C32—C31—H31A108.2
C13—C15—H15C109.5N5—C31—H31A108.2
H15A—C15—H15C109.5C32—C31—H31B108.2
H15B—C15—H15C109.5N5—C31—H31B108.2
C13—C16—H16A109.5H31A—C31—H31B107.4
C13—C16—H16B109.5C31—C32—H32A109.5
H16A—C16—H16B109.5C31—C32—H32B109.5
C13—C16—H16C109.5H32A—C32—H32B109.5
H16A—C16—H16C109.5C31—C32—H32C109.5
H16B—C16—H16C109.5H32A—C32—H32C109.5
O2—C17—N3127.9 (4)H32B—C32—H32C109.5
O2—C17—C18119.3 (4)C34—C33—N5116.1 (5)
N3—C17—C18112.7 (4)C34—C33—H33A108.3
N4—C18—C19122.3 (4)N5—C33—H33A108.3
N4—C18—C17116.4 (4)C34—C33—H33B108.3
C19—C18—C17121.3 (4)N5—C33—H33B108.3
C18—C19—C20120.6 (4)H33A—C33—H33B107.4
C18—C19—H19119.7C33—C34—H34A109.5
C20—C19—H19119.7C33—C34—H34B109.5
C21—C20—C19115.8 (4)H34A—C34—H34B109.5
C21—C20—C23121.8 (4)C33—C34—H34C109.5
C19—C20—C23122.4 (4)H34A—C34—H34C109.5
C22—C21—C20121.1 (4)H34B—C34—H34C109.5
C22—C21—H21119.5Cl2A—C35A—Cl11113.2 (6)
C20—C21—H21119.5Cl2A—C35A—Cl3A107.0 (5)
N4—C22—C21122.1 (4)Cl11—C35A—Cl3A109.2 (7)
N4—C22—H22119.0Cl2A—C35A—H35A109.1
C21—C22—H22119.0Cl11—C35A—H35A109.1
C26A—C23—C26B30.5 (8)Cl3A—C35A—H35A109.1
C26A—C23—C20113.2 (8)
Acknowledgements top

The Project was sponsored by the Scientific Research Foundation for

Returned Overseas Chinese Scholars, State Education Ministry of China. We also thank the State Key Laboratory of Coordination Chemistry of Nanjing University and Sichuan University for financial support.

references
References top

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