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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807021915/dn2152sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807021915/dn2152Isup2.hkl
Contains datablock I

CCDC reference: 288283

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.007 Å
  • Disorder in main residue
  • R factor = 0.064
  • wR factor = 0.202
  • Data-to-parameter ratio = 21.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 47 Perc. PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.91 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.32 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C13 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C23 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N5 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C31 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C35A PLAT301_ALERT_3_C Main Residue Disorder ......................... 8.00 Perc. PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 7 PLAT432_ALERT_2_C Short Inter X...Y Contact O1 .. C35A .. 2.94 Ang. PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 30.50 Deg. C26A -C23 -C26B 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 36.60 Deg. C24B -C23 -C24A 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 38.10 Deg. C25A -C23 -C25B 1.555 1.555 1.555
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 6
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 16 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 7 ALERT type 2 Indicator that the structure model may be wrong or deficient 6 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

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.

Structure description 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).

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).

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]·CHCl3F(000) = 1812
Mr = 873.78Dx = 1.372 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 8783 reflections
a = 11.1740 (17) Åθ = 1–27.5°
b = 26.598 (4) ŵ = 0.84 mm1
c = 15.000 (2) ÅT = 294 K
β = 108.380 (3)°Needle, 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)
Graphite monochromatorRint = 0.082
φ and ω scansθmax = 27.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1414
Tmin = 0.742, Tmax = 0.906k = 3424
28612 measured reflectionsl = 1919
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)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.202H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0902P)2 + 1.0929P]
where P = (Fo2 + 2Fc2)/3
9757 reflections(Δ/σ)max = 0.001
461 parametersΔρmax = 0.82 e Å3
6 restraintsΔρmin = 0.72 e Å3
Crystal data top
(C8H20N)[Fe(C26H26Cl2N4O2)Cl2]·CHCl3V = 4230.9 (11) Å3
Mr = 873.78Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.1740 (17) ŵ = 0.84 mm1
b = 26.598 (4) ÅT = 294 K
c = 15.000 (2) Å0.38 × 0.16 × 0.12 mm
β = 108.380 (3)°
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 Å3
9757 reflectionsΔρmin = 0.72 e Å3
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)
H14A0.14230.53740.05420.124*
H14B0.10900.55770.03320.124*
H14C0.23260.52650.04740.124*
C150.1525 (6)0.6372 (2)0.0550 (4)0.0752 (17)
H15A0.10970.62250.11500.113*
H15B0.19550.66710.06380.113*
H15C0.09220.64550.02380.113*
C160.3521 (6)0.5890 (3)0.0374 (5)0.110 (3)
H16A0.40690.56330.00190.166*
H16B0.39970.61920.03640.166*
H16C0.31530.57800.10110.166*
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*
Cl2A0.0355 (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, º) 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)

Experimental details

Crystal data
Chemical formula(C8H20N)[Fe(C26H26Cl2N4O2)Cl2]·CHCl3
Mr873.78
Crystal system, space groupMonoclinic, P21/c
Temperature (K)294
a, b, c (Å)11.1740 (17), 26.598 (4), 15.000 (2)
β (°) 108.380 (3)
V3)4230.9 (11)
Z4
Radiation typeMo Kα
µ (mm1)0.84
Crystal size (mm)0.38 × 0.16 × 0.12
Data collection
DiffractometerBruker CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.742, 0.906
No. of measured, independent and
observed [I > 2σ(I)] reflections
28612, 9757, 4586
Rint0.082
(sin θ/λ)max1)0.651
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.064, 0.202, 1.01
No. of reflections9757
No. of parameters461
No. of restraints6
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.82, 0.72

Computer programs: SMART (Bruker, 1997), SMART, SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Sheldrick, 1998), SHELXTL.

 

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