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Acta Cryst. (2009). E65, m828    [ doi:10.1107/S1600536809023423 ]

Dichlorido[tris(1H-benzimidazol-2-ylmethyl)amine-[kappa]4N,N3,N3',N3'']iron(III) chloride tetrahydrofuran monosolvate monohydrate

D. Wang

Abstract top

In the title compound, [FeCl2(C24H21N7)]Cl·C4H8O·H2O, the FeIII atom is coordinated by four N atoms of the polybenzimidazole ligand and two Cl atoms in a distorted octahedral environment. The cation, anion, the uncoordinated water molecule and the THF solvent molecule are linked by hydrogen bonds into a three-dimensional network structure. The THF molecule is disordered with two sets of sites in a 0.58 (1):0.42 (2) ratio..

Comment top

Tris(1-H-benzimidazol-2-ylmethl)amine-N, H3ntb, is a typical heterocyclic ligand with nitrogen as the donor atom. Over the past decades, there has been an interest in the FeIII ions coordinated to benzimidazole-rich ligands in particular with respect to relationships between the activity and structural properties of metalloenzymes such as superoxide dismutases (SOD) (Moon & Soo Lah, 2002). Here, we report our findings in the title compound (I).

In compound (I) (Fig.1), the asymmetric unit consists of one [Fe(H3ntb).Cl2]+ cation, one Cl- anion and each one water and tetrahydrofuran molecules. The FeIII is coordinated by four nitrogen atoms of a tetradentate liangd ntb, and two chloride anions, forming a distorted octahedron. The Fe—Namine bond length (2.355 (2) Å) is more longer than the mean bond length of Fe—Nbenzimidazole (2.101 (2) Å), which is owing to the steric requirement. No other abnormal bond lengths and bond angles are observed in (I).

In the crystal, the ions are joined together by extensive hydrogen bondings and and π-π interactions, which lead to the formation of a three dimensional network (Fig.2).

Related literature top

For the synthesis of the ligand, see: Hendriks et al. (1982). For benzimidazole-like ligands, see: Moon & Soo Lah (2002); Sheldrick (2001).

Experimental top

All reagants and solvents were used as obtained without further purification. H3ntb was synthesized according to the literature (Hendriks et al.,1982). A mixture of FeCl3 (0.0324 g, 0.2 mmol), H3ntb(0.0814 g, 0.2 mmol), tetrahydrofuran (5 ml)was transferred to and sealed in a Parr Teflon-lined stainless steel vessel (15 ml), which was heated at 393 K for 3 days. After cooling to room temperature, the red block crystals of I were filtered off, washed with distilled water, and dried at ambient temperature (39 mg, yield 28.7% based on FeCl3).

Refinement top

During the refinement, C27 and C28 atoms were founded to be disordered over two positions and their occupancies were refined by using 'PART' command and some C–O and C–C distance of the THF molecule were refined by using command of 'DFIX'. The final satisfactory outcome was 0.58 (1):0.45 (2) for the major and minor components, respectively. H atoms bonded to carbon atoms were located at the geometrical positions with C—H=0.93Å (aromatic), 0.97 Å (methylene) and Uiso(H) =1.2Ueq(C) (aromatic and methlene). H atoms bonded N and O atoms were found from the difference maps with the constraints of N—H=0.86 (1) Å, O—H=0.82 (1) Å and H—H=1.35 (1) Å, with the thermal factors being set k times of their carrier atoms (k=1.2 for N and 1.5 for O atoms).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. A view of the structure of (I), with displacement ellipsoids drawn at the 30% probability level. Hydrogen bonds are shown as dashed lines.
[Figure 2] Fig. 2. Plot of the crystal packing showing the linkage of the molecules by H-bonding shown as dashed lines.
Dichlorido[tris(1H-benzimidazol-2-ylmethyl)amine- κ4N,N3,N3',N3'']iron(III) chloride tetrahydrofuran monosolvate monohydrate top
Crystal data top
[FeCl2(C24H21N7)]Cl·C4H8O·H2OF(000) = 1364
Mr = 659.80Dx = 1.469 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3638 reflections
a = 10.2898 (4) Åθ = 2.4–22.2°
b = 13.7475 (5) ŵ = 0.81 mm−1
c = 21.5271 (7) ÅT = 292 K
β = 101.614 (1)°Block, red
V = 2982.85 (19) Å30.20 × 0.15 × 0.10 mm
Z = 4
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		5527 independent reflections
Radiation source: fine focus sealed Siemens Mo tube3999 reflections with I > 2σ(I)
graphiteRint = 0.046
0.3° wide ω exposures scansθmax = 25.5°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)		h = −12→12
Tmin = 0.844, Tmax = 0.923k = −16→15
17337 measured reflectionsl = −26→24
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.0587P)2]
where P = (Fo2 + 2Fc2)/3
5527 reflections(Δ/σ)max < 0.001
404 parametersΔρmax = 0.33 e Å−3
21 restraintsΔρmin = −0.25 e Å−3
Crystal data top
[FeCl2(C24H21N7)]Cl·C4H8O·H2OV = 2982.85 (19) Å3
Mr = 659.80Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.2898 (4) ŵ = 0.81 mm−1
b = 13.7475 (5) ÅT = 292 K
c = 21.5271 (7) Å0.20 × 0.15 × 0.10 mm
β = 101.614 (1)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		5527 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)		3999 reflections with I > 2σ(I)
Tmin = 0.844, Tmax = 0.923Rint = 0.046
17337 measured reflectionsθmax = 25.5°
Refinement top
R[F2 > 2σ(F2)] = 0.047H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.116Δρmax = 0.33 e Å−3
S = 1.00Δρmin = −0.25 e Å−3
5527 reflectionsAbsolute structure: ?
404 parametersFlack parameter: ?
21 restraintsRogers parameter: ?
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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)
Fe10.94620 (4)0.27332 (3)0.810133 (19)0.03211 (14)
Cl11.00873 (8)0.17478 (6)0.73359 (4)0.0445 (2)
Cl20.86507 (8)0.39490 (6)0.74462 (4)0.0476 (2)
N10.7813 (2)0.18448 (19)0.81255 (12)0.0369 (6)
N20.6965 (3)0.0441 (2)0.83683 (14)0.0482 (7)
H20.694 (3)−0.0126 (16)0.8535 (15)0.058*
N30.9114 (2)0.33689 (18)0.89433 (11)0.0367 (6)
N40.9099 (3)0.3256 (2)0.99701 (12)0.0439 (7)
H40.924 (3)0.296 (2)1.0330 (11)0.053*
N51.1468 (2)0.30502 (18)0.84551 (11)0.0342 (6)
N61.3466 (2)0.2668 (2)0.89915 (13)0.0446 (7)
H61.413 (2)0.237 (2)0.9213 (14)0.054*
N71.0223 (2)0.15132 (18)0.88547 (11)0.0361 (6)
C10.5896 (3)0.0998 (3)0.80784 (15)0.0452 (8)
C20.4545 (3)0.0799 (3)0.79198 (18)0.0604 (10)
H2A0.41910.02100.80190.072*
C30.3760 (4)0.1536 (3)0.76056 (18)0.0635 (11)
H30.28510.14330.74870.076*
C40.4273 (3)0.2419 (3)0.74607 (18)0.0596 (10)
H4A0.37030.28930.72510.071*
C50.5621 (3)0.2610 (3)0.76226 (16)0.0508 (9)
H50.59680.32030.75260.061*
C60.6426 (3)0.1889 (2)0.79315 (14)0.0392 (8)
C70.8062 (3)0.0962 (2)0.83803 (15)0.0407 (8)
C80.9449 (3)0.0627 (2)0.86263 (16)0.0428 (8)
H8A0.94770.01670.89700.051*
H8B0.98060.03150.82920.051*
C90.9971 (3)0.1834 (3)0.94789 (15)0.0483 (9)
H9A0.93720.13760.96190.058*
H9B1.08000.18250.97870.058*
C100.9390 (3)0.2821 (2)0.94594 (14)0.0368 (7)
C110.8612 (3)0.4177 (3)0.97900 (15)0.0424 (8)
C120.8176 (3)0.4915 (3)1.01283 (17)0.0539 (9)
H120.81510.48521.05560.065*
C130.7781 (3)0.5753 (3)0.9795 (2)0.0586 (10)
H130.74790.62711.00050.070*
C140.7816 (3)0.5853 (3)0.91592 (18)0.0516 (9)
H140.75550.64380.89550.062*
C150.8229 (3)0.5102 (2)0.88240 (16)0.0451 (8)
H150.82390.51660.83950.054*
C160.8624 (3)0.4259 (2)0.91432 (15)0.0378 (7)
C171.1664 (3)0.1394 (2)0.88752 (16)0.0412 (8)
H17A1.20990.11260.92810.049*
H17B1.18070.09560.85420.049*
C181.2211 (3)0.2369 (2)0.87831 (14)0.0349 (7)
C191.3560 (3)0.3620 (2)0.87884 (14)0.0402 (8)
C201.4596 (3)0.4284 (3)0.88702 (17)0.0552 (10)
H201.54440.41240.90890.066*
C211.4307 (3)0.5183 (3)0.86141 (17)0.0568 (10)
H211.49790.56450.86570.068*
C221.3051 (3)0.5433 (3)0.82922 (16)0.0514 (9)
H221.28980.60620.81360.062*
C231.2022 (3)0.4777 (2)0.81965 (15)0.0421 (8)
H231.11810.49440.79730.051*
C241.2294 (3)0.3859 (2)0.84485 (14)0.0361 (7)
O1W0.9939 (3)0.2955 (2)0.60165 (12)0.0715 (8)
H1A1.073 (2)0.302 (4)0.599 (2)0.107*
H1B0.984 (4)0.283 (4)0.6383 (12)0.107*
Cl31.26515 (10)0.36822 (8)0.57345 (5)0.0690 (3)
O10.5693 (3)0.2940 (2)0.48243 (13)0.0781 (9)
C250.5735 (5)0.2366 (3)0.5376 (2)0.0854 (14)
H25A0.62370.17760.53490.102*
H25B0.48420.21840.54130.102*
C260.6369 (5)0.2936 (4)0.5937 (2)0.0999 (17)
H26A0.72680.27140.60980.120*0.58
H26B0.58670.28880.62720.120*0.58
H26C0.71380.25980.61740.120*0.42
H26D0.57540.30580.62150.120*0.42
C270.6360 (17)0.3975 (6)0.5690 (5)0.088 (6)0.58
H27A0.71140.43450.59130.106*0.58
H27B0.55450.43120.57170.106*0.58
C280.6462 (10)0.3772 (7)0.4990 (5)0.084 (4)0.58
H28A0.61150.43140.47190.101*0.58
H28B0.73760.36570.49560.101*0.58
C28'0.5865 (15)0.3944 (7)0.4996 (6)0.085 (5)0.42
H28C0.50240.42470.50180.102*0.42
H28D0.62770.42990.46980.102*0.42
C27'0.679 (2)0.3894 (9)0.5661 (6)0.084 (7)0.42
H27C0.77170.38730.56260.101*0.42
H27D0.66530.44470.59200.101*0.42
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0333 (2)0.0318 (3)0.0293 (2)0.00082 (18)0.00167 (17)0.00084 (19)
Cl10.0463 (4)0.0451 (5)0.0424 (5)0.0001 (4)0.0096 (3)−0.0090 (4)
Cl20.0550 (5)0.0437 (5)0.0397 (5)0.0064 (4)−0.0010 (4)0.0092 (4)
N10.0365 (14)0.0339 (16)0.0391 (15)−0.0016 (11)0.0046 (11)0.0021 (12)
N20.0503 (17)0.0416 (18)0.0534 (19)−0.0107 (15)0.0116 (14)0.0037 (15)
N30.0415 (14)0.0363 (16)0.0308 (14)0.0033 (11)0.0037 (11)−0.0003 (12)
N40.0504 (16)0.052 (2)0.0296 (15)0.0020 (14)0.0084 (13)0.0017 (14)
N50.0340 (13)0.0291 (14)0.0363 (15)−0.0007 (11)−0.0006 (11)−0.0004 (12)
N60.0359 (15)0.0472 (19)0.0453 (17)0.0058 (13)−0.0050 (12)0.0021 (14)
N70.0405 (14)0.0316 (15)0.0348 (14)0.0048 (11)0.0041 (11)0.0013 (12)
C10.0414 (18)0.055 (2)0.0401 (19)−0.0032 (16)0.0109 (15)−0.0033 (17)
C20.049 (2)0.078 (3)0.058 (2)−0.020 (2)0.0176 (18)−0.010 (2)
C30.0372 (19)0.098 (3)0.056 (2)−0.004 (2)0.0101 (17)−0.018 (2)
C40.042 (2)0.077 (3)0.057 (2)0.0144 (19)0.0026 (17)0.000 (2)
C50.049 (2)0.054 (2)0.050 (2)0.0040 (17)0.0093 (17)−0.0025 (18)
C60.0365 (17)0.047 (2)0.0348 (18)0.0014 (15)0.0079 (14)−0.0036 (15)
C70.0407 (17)0.040 (2)0.0416 (19)−0.0035 (15)0.0084 (14)−0.0015 (16)
C80.0458 (18)0.0325 (19)0.048 (2)0.0013 (14)0.0037 (15)0.0033 (16)
C90.061 (2)0.047 (2)0.0361 (19)0.0098 (17)0.0095 (16)0.0042 (16)
C100.0384 (16)0.040 (2)0.0309 (17)−0.0004 (14)0.0047 (13)0.0000 (15)
C110.0401 (17)0.044 (2)0.043 (2)−0.0008 (15)0.0082 (15)−0.0065 (16)
C120.057 (2)0.058 (3)0.050 (2)−0.0008 (18)0.0179 (17)−0.016 (2)
C130.056 (2)0.049 (2)0.074 (3)0.0028 (18)0.0196 (19)−0.023 (2)
C140.0475 (19)0.043 (2)0.062 (2)0.0049 (16)0.0045 (17)−0.0037 (19)
C150.0487 (19)0.037 (2)0.048 (2)0.0072 (15)0.0054 (15)−0.0022 (17)
C160.0340 (16)0.040 (2)0.0391 (19)0.0007 (14)0.0059 (13)−0.0056 (15)
C170.0386 (17)0.0341 (19)0.048 (2)0.0068 (14)0.0005 (14)0.0033 (16)
C180.0360 (16)0.0300 (18)0.0352 (17)0.0039 (13)−0.0010 (13)−0.0027 (14)
C190.0375 (17)0.041 (2)0.0401 (19)−0.0015 (14)0.0025 (14)−0.0003 (16)
C200.0357 (18)0.070 (3)0.054 (2)−0.0071 (17)−0.0051 (16)0.000 (2)
C210.051 (2)0.056 (3)0.061 (2)−0.0186 (18)0.0048 (18)0.004 (2)
C220.058 (2)0.047 (2)0.048 (2)−0.0103 (17)0.0088 (17)0.0069 (18)
C230.0450 (18)0.042 (2)0.0383 (18)−0.0008 (15)0.0056 (14)0.0053 (16)
C240.0380 (16)0.039 (2)0.0295 (16)−0.0019 (14)0.0038 (13)−0.0051 (14)
O1W0.082 (2)0.088 (2)0.0449 (16)−0.0061 (18)0.0147 (14)−0.0079 (16)
Cl30.0691 (6)0.0644 (7)0.0706 (7)−0.0083 (5)0.0075 (5)−0.0187 (5)
O10.081 (2)0.082 (2)0.0597 (19)−0.0229 (17)−0.0139 (14)−0.0003 (17)
C250.083 (3)0.075 (3)0.093 (4)−0.005 (2)0.006 (3)0.013 (3)
C260.102 (4)0.119 (5)0.072 (3)−0.026 (3)0.002 (3)−0.006 (3)
C270.083 (9)0.089 (10)0.086 (10)−0.010 (7)0.001 (6)−0.027 (7)
C280.072 (7)0.078 (7)0.105 (9)−0.002 (5)0.024 (6)0.026 (6)
C28'0.088 (12)0.079 (11)0.091 (11)−0.024 (8)0.023 (9)0.000 (8)
C27'0.087 (14)0.069 (11)0.080 (13)0.020 (7)−0.021 (8)−0.021 (8)
Geometric parameters (Å, °) top
Fe1—N52.097 (2)C13—C141.384 (5)
Fe1—N12.100 (2)C13—H130.9300
Fe1—N32.107 (2)C14—C151.375 (4)
Fe1—Cl22.2373 (9)C14—H140.9300
Fe1—Cl12.3219 (9)C15—C161.367 (4)
Fe1—N72.355 (2)C15—H150.9300
Cl1—H1B2.51 (3)C17—C181.482 (4)
N1—C71.335 (4)C17—H17A0.9700
N1—C61.405 (4)C17—H17B0.9700
N2—C71.333 (4)C19—C201.387 (4)
N2—C11.382 (4)C19—C241.399 (4)
N2—H20.859 (18)C20—C211.361 (5)
N3—C101.325 (4)C20—H200.9300
N3—C161.422 (4)C21—C221.381 (5)
N4—C101.338 (4)C21—H210.9300
N4—C111.388 (4)C22—C231.375 (4)
N4—H40.862 (18)C22—H220.9300
N5—C181.320 (4)C23—C241.379 (4)
N5—C241.402 (4)C23—H230.9300
N6—C181.343 (4)O1W—H1A0.828 (18)
N6—C191.389 (4)O1W—H1B0.831 (19)
N6—H60.852 (18)Cl3—H1A2.34 (2)
N7—C81.484 (4)O1—C281.395 (8)
N7—C171.484 (4)O1—C251.420 (5)
N7—C91.486 (4)O1—C28'1.430 (9)
C1—C21.391 (4)C25—C261.476 (5)
C1—C61.403 (4)C25—H25A0.9700
C2—C31.384 (5)C25—H25B0.9700
C2—H2A0.9300C26—C271.523 (8)
C3—C41.385 (6)C26—C27'1.544 (9)
C3—H30.9300C26—H26A0.9700
C4—C51.386 (5)C26—H26B0.9700
C4—H4A0.9300C26—H26C0.9700
C5—C61.374 (5)C26—H26D0.9700
C5—H50.9300C27—C281.556 (9)
C7—C81.492 (4)C27—H27A0.9700
C8—H8A0.9700C27—H27B0.9700
C8—H8B0.9700C28—H28A0.9700
C9—C101.479 (4)C28—H28B0.9700
C9—H9A0.9700C28'—C27'1.553 (10)
C9—H9B0.9700C28'—H28C0.9700
C11—C121.376 (5)C28'—H28D0.9700
C11—C161.400 (4)C27'—H27C0.9700
C12—C131.374 (5)C27'—H27D0.9700
C12—H120.9300
N5—Fe1—N1148.56 (10)C15—C14—H14119.4
N5—Fe1—N385.80 (9)C13—C14—H14119.4
N1—Fe1—N386.65 (10)C16—C15—C14117.7 (3)
N5—Fe1—Cl2106.78 (7)C16—C15—H15121.1
N1—Fe1—Cl2104.43 (7)C14—C15—H15121.1
N3—Fe1—Cl297.23 (7)C15—C16—C11120.4 (3)
N5—Fe1—Cl189.19 (7)C15—C16—N3131.7 (3)
N1—Fe1—Cl191.09 (7)C11—C16—N3107.9 (3)
N3—Fe1—Cl1166.40 (7)C18—C17—N7107.5 (2)
Cl2—Fe1—Cl196.32 (3)C18—C17—H17A110.2
N5—Fe1—N774.41 (9)N7—C17—H17A110.2
N1—Fe1—N774.16 (9)C18—C17—H17B110.2
N3—Fe1—N778.09 (9)N7—C17—H17B110.2
Cl2—Fe1—N7175.13 (7)H17A—C17—H17B108.5
Cl1—Fe1—N788.40 (6)N5—C18—N6112.1 (3)
Fe1—Cl1—H1B103.7 (10)N5—C18—C17121.2 (3)
C7—N1—C6105.1 (2)N6—C18—C17126.7 (3)
C7—N1—Fe1116.72 (19)C20—C19—N6132.9 (3)
C6—N1—Fe1138.1 (2)C20—C19—C24121.5 (3)
C7—N2—C1107.7 (3)N6—C19—C24105.6 (3)
C7—N2—H2125 (2)C21—C20—C19116.5 (3)
C1—N2—H2127 (2)C21—C20—H20121.8
C10—N3—C16105.4 (2)C19—C20—H20121.8
C10—N3—Fe1116.1 (2)C20—C21—C22122.4 (3)
C16—N3—Fe1138.5 (2)C20—C21—H21118.8
C10—N4—C11107.9 (3)C22—C21—H21118.8
C10—N4—H4120 (2)C23—C22—C21121.8 (3)
C11—N4—H4132 (2)C23—C22—H22119.1
C18—N5—C24106.3 (2)C21—C22—H22119.1
C18—N5—Fe1118.0 (2)C22—C23—C24116.8 (3)
C24—N5—Fe1135.7 (2)C22—C23—H23121.6
C18—N6—C19107.9 (2)C24—C23—H23121.6
C18—N6—H6130 (2)C23—C24—C19121.0 (3)
C19—N6—H6122 (2)C23—C24—N5130.9 (3)
C8—N7—C17112.7 (2)C19—C24—N5108.1 (3)
C8—N7—C9111.3 (2)H1A—O1W—H1B113 (3)
C17—N7—C9111.2 (2)C28—O1—C25108.8 (5)
C8—N7—Fe1105.93 (17)C25—O1—C28'109.8 (6)
C17—N7—Fe1106.90 (17)C28—O1—H4A93.5
C9—N7—Fe1108.49 (18)O1—C25—C26108.8 (3)
N2—C1—C2131.9 (3)O1—C25—H25A109.9
N2—C1—C6106.0 (3)C26—C25—H25A109.9
C2—C1—C6122.0 (3)O1—C25—H25B109.9
C3—C2—C1115.6 (4)C26—C25—H25B109.9
C3—C2—H2A122.2H25A—C25—H25B108.3
C1—C2—H2A122.2C25—C26—C27104.0 (5)
C2—C3—C4122.7 (3)C25—C26—C27'104.5 (6)
C2—C3—H3118.6C25—C26—H26A111.0
C4—C3—H3118.6C27—C26—H26A111.0
C3—C4—C5121.1 (4)C27'—C26—H26A94.8
C3—C4—H4A119.4C25—C26—H26B111.0
C5—C4—H4A119.4C27—C26—H26B111.0
C6—C5—C4117.4 (4)C27'—C26—H26B125.4
C6—C5—H5121.3H26A—C26—H26B109.0
C4—C5—H5121.3C25—C26—H26C110.8
C5—C6—C1121.1 (3)C27—C26—H26C125.4
C5—C6—N1130.7 (3)C27'—C26—H26C110.4
C1—C6—N1108.2 (3)H26B—C26—H26C94.3
N2—C7—N1112.9 (3)C25—C26—H26D111.2
N2—C7—C8126.0 (3)C27'—C26—H26D111.1
N1—C7—C8121.1 (3)H26A—C26—H26D121.8
N7—C8—C7106.0 (2)H26C—C26—H26D108.7
N7—C8—H8A110.5C26—C27—C28100.0 (7)
C7—C8—H8A110.5C26—C27—H27A111.8
N7—C8—H8B110.5C28—C27—H27A111.8
C7—C8—H8B110.5C26—C27—H27B111.8
H8A—C8—H8B108.7C28—C27—H27B111.8
C10—C9—N7112.9 (3)H27A—C27—H27B109.5
C10—C9—H9A109.0O1—C28—C27104.4 (7)
N7—C9—H9A109.0O1—C28—H28A110.9
C10—C9—H9B109.0C27—C28—H28A110.9
N7—C9—H9B109.0O1—C28—H28B110.9
H9A—C9—H9B107.8C27—C28—H28B110.9
N3—C10—N4112.9 (3)H28A—C28—H28B108.9
N3—C10—C9124.3 (3)O1—C28'—C27'102.5 (8)
N4—C10—C9122.9 (3)O1—C28'—H28C111.3
C12—C11—N4131.5 (3)C27'—C28'—H28C111.3
C12—C11—C16122.5 (3)O1—C28'—H28D111.3
N4—C11—C16106.0 (3)C27'—C28'—H28D111.3
C13—C12—C11115.9 (3)H28C—C28'—H28D109.2
C13—C12—H12122.1C26—C27'—C28'102.9 (8)
C11—C12—H12122.1C26—C27'—H27C111.2
C12—C13—C14122.4 (3)C28'—C27'—H27C111.2
C12—C13—H13118.8C26—C27'—H27D111.2
C14—C13—H13118.8C28'—C27'—H27D111.2
C15—C14—C13121.1 (4)H27C—C27'—H27D109.1
N5—Fe1—Cl1—H1B−96.2 (10)N1—C7—C8—N730.8 (4)
N1—Fe1—Cl1—H1B115.2 (10)C8—N7—C9—C10−118.9 (3)
N3—Fe1—Cl1—H1B−164.5 (10)C17—N7—C9—C10114.5 (3)
Cl2—Fe1—Cl1—H1B10.6 (10)Fe1—N7—C9—C10−2.7 (3)
N7—Fe1—Cl1—H1B−170.7 (10)C16—N3—C10—N41.5 (3)
N5—Fe1—N1—C7−20.2 (3)Fe1—N3—C10—N4−177.65 (19)
N3—Fe1—N1—C7−96.6 (2)C16—N3—C10—C9−177.9 (3)
Cl2—Fe1—N1—C7166.8 (2)Fe1—N3—C10—C92.9 (4)
Cl1—Fe1—N1—C770.0 (2)C11—N4—C10—N3−1.2 (3)
N7—Fe1—N1—C7−18.0 (2)C11—N4—C10—C9178.3 (3)
N5—Fe1—N1—C6161.4 (3)N7—C9—C10—N30.2 (5)
N3—Fe1—N1—C685.1 (3)N7—C9—C10—N4−179.2 (3)
Cl2—Fe1—N1—C6−11.6 (3)C10—N4—C11—C12−179.8 (3)
Cl1—Fe1—N1—C6−108.4 (3)C10—N4—C11—C160.4 (3)
N7—Fe1—N1—C6163.6 (3)N4—C11—C12—C13178.6 (3)
N5—Fe1—N3—C10−78.2 (2)C16—C11—C12—C13−1.5 (5)
N1—Fe1—N3—C1071.3 (2)C11—C12—C13—C140.0 (5)
Cl2—Fe1—N3—C10175.4 (2)C12—C13—C14—C151.3 (5)
Cl1—Fe1—N3—C10−9.5 (4)C13—C14—C15—C16−1.0 (5)
N7—Fe1—N3—C10−3.2 (2)C14—C15—C16—C11−0.5 (5)
N5—Fe1—N3—C16103.0 (3)C14—C15—C16—N3−179.0 (3)
N1—Fe1—N3—C16−107.5 (3)C12—C11—C16—C151.8 (5)
Cl2—Fe1—N3—C16−3.4 (3)N4—C11—C16—C15−178.3 (3)
Cl1—Fe1—N3—C16171.7 (2)C12—C11—C16—N3−179.3 (3)
N7—Fe1—N3—C16178.0 (3)N4—C11—C16—N30.5 (3)
N1—Fe1—N5—C1816.6 (3)C10—N3—C16—C15177.4 (3)
N3—Fe1—N5—C1893.2 (2)Fe1—N3—C16—C15−3.7 (5)
Cl2—Fe1—N5—C18−170.5 (2)C10—N3—C16—C11−1.2 (3)
Cl1—Fe1—N5—C18−74.2 (2)Fe1—N3—C16—C11177.6 (2)
N7—Fe1—N5—C1814.4 (2)C8—N7—C17—C18151.7 (3)
N1—Fe1—N5—C24−161.7 (2)C9—N7—C17—C18−82.5 (3)
N3—Fe1—N5—C24−85.1 (3)Fe1—N7—C17—C1835.7 (3)
Cl2—Fe1—N5—C2411.2 (3)C24—N5—C18—N6−0.2 (3)
Cl1—Fe1—N5—C24107.6 (3)Fe1—N5—C18—N6−178.9 (2)
N7—Fe1—N5—C24−163.9 (3)C24—N5—C18—C17−178.6 (3)
N5—Fe1—N7—C8−148.3 (2)Fe1—N5—C18—C172.7 (4)
N1—Fe1—N7—C832.90 (18)C19—N6—C18—N50.2 (4)
N3—Fe1—N7—C8122.78 (19)C19—N6—C18—C17178.5 (3)
Cl1—Fe1—N7—C8−58.69 (18)N7—C17—C18—N5−28.4 (4)
N5—Fe1—N7—C17−27.88 (18)N7—C17—C18—N6153.5 (3)
N1—Fe1—N7—C17153.3 (2)C18—N6—C19—C20179.1 (4)
N3—Fe1—N7—C17−116.80 (19)C18—N6—C19—C24−0.2 (3)
Cl1—Fe1—N7—C1761.73 (17)N6—C19—C20—C21−177.9 (4)
N5—Fe1—N7—C992.1 (2)C24—C19—C20—C211.3 (5)
N1—Fe1—N7—C9−86.7 (2)C19—C20—C21—C220.4 (6)
N3—Fe1—N7—C93.18 (19)C20—C21—C22—C23−1.7 (6)
Cl1—Fe1—N7—C9−178.29 (19)C21—C22—C23—C241.2 (5)
C7—N2—C1—C2176.9 (3)C22—C23—C24—C190.5 (5)
C7—N2—C1—C6−1.2 (4)C22—C23—C24—N5177.4 (3)
N2—C1—C2—C3−177.6 (3)C20—C19—C24—C23−1.8 (5)
C6—C1—C2—C30.3 (5)N6—C19—C24—C23177.6 (3)
C1—C2—C3—C4−0.6 (5)C20—C19—C24—N5−179.3 (3)
C2—C3—C4—C50.4 (6)N6—C19—C24—N50.1 (3)
C3—C4—C5—C60.0 (5)C18—N5—C24—C23−177.2 (3)
C4—C5—C6—C1−0.3 (5)Fe1—N5—C24—C231.3 (5)
C4—C5—C6—N1176.4 (3)C18—N5—C24—C190.0 (3)
N2—C1—C6—C5178.5 (3)Fe1—N5—C24—C19178.5 (2)
C2—C1—C6—C50.1 (5)C28—O1—C25—C2610.0 (7)
N2—C1—C6—N11.2 (3)C28'—O1—C25—C26−18.6 (8)
C2—C1—C6—N1−177.2 (3)H4A—O1—C25—C26−61.4
C7—N1—C6—C5−177.6 (3)O1—C25—C26—C2714.7 (8)
Fe1—N1—C6—C50.9 (5)O1—C25—C26—C27'−3.7 (11)
C7—N1—C6—C1−0.6 (3)C25—C26—C27—C28−30.5 (10)
Fe1—N1—C6—C1177.9 (2)C27'—C26—C27—C2864 (2)
C1—N2—C7—N10.9 (4)C25—O1—C28—C27−30.0 (10)
C1—N2—C7—C8−177.3 (3)C28'—O1—C28—C2767.0 (18)
C6—N1—C7—N2−0.1 (4)H4A—O1—C28—C276.6
Fe1—N1—C7—N2−179.0 (2)C26—C27—C28—O137.2 (11)
C6—N1—C7—C8178.1 (3)C28—O1—C28'—C27'−60.6 (18)
Fe1—N1—C7—C8−0.8 (4)C25—O1—C28'—C27'32.1 (13)
C17—N7—C8—C7−157.2 (2)H4A—O1—C28'—C27'57.8
C9—N7—C8—C777.1 (3)C25—C26—C27'—C28'22.1 (15)
Fe1—N7—C8—C7−40.6 (3)C27—C26—C27'—C28'−68 (2)
N2—C7—C8—N7−151.2 (3)O1—C28'—C27'—C26−32.6 (16)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1W—H1A···Cl30.83 (2)2.34 (2)3.136 (3)160 (4)
O1W—H1B···Cl10.83 (2)2.51 (3)3.267 (3)152 (4)
C23—H23···Cl1i0.932.823.516 (3)133
N2—H2···Cl3ii0.86 (2)2.25 (2)3.070 (3)159 (3)
N4—H4···O1Wiii0.86 (2)1.96 (2)2.795 (4)162 (3)
N6—H6···O1iv0.85 (2)1.91 (2)2.741 (4)163 (3)
C9—H9B···Cl3iii0.972.593.523 (3)162
C3—H3···Cl1v0.932.833.718 (4)160
C15—H15···Cl20.932.743.466 (3)136
Symmetry codes: (i) −x+2, y+1/2, −z+3/2; (ii) −x+2, y−1/2, −z+3/2; (iii) x, −y+1/2, z+1/2; (iv) x+1, −y+1/2, z+1/2; (v) x−1, y, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1W—H1A···Cl30.83 (2)2.34 (2)3.136 (3)160 (4)
O1W—H1B···Cl10.83 (2)2.51 (3)3.267 (3)152 (4)
N2—H2···Cl3i0.86 (2)2.25 (2)3.070 (3)159 (3)
N4—H4···O1Wii0.86 (2)1.96 (2)2.795 (4)162 (3)
N6—H6···O1iii0.85 (2)1.91 (2)2.741 (4)163 (3)
Symmetry codes: (i) −x+2, y−1/2, −z+3/2; (ii) x, −y+1/2, z+1/2; (iii) x+1, −y+1/2, z+1/2.
references
References top

Bruker (2001). SAINT-Plus and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.

Hendriks, M. J., Birker, J. M. W. L., van Rijn, J., Verschoor, G. C. & Reedijk, J. (1982). J. Am. Chem. Soc. 104, 3607–3617.

Moon, D. & Soo Lah, M. (2002). Inorg. Chem. 41, 4708–4714.

Sheldrick, G. M. (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Spek, A. L. (2009). Acta Cryst. D65, 148–155.