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Acta Crystallogr Sect E Struct Rep Online. 2009 July 1; 65(Pt 7): m828.
Published online 2009 June 27. doi:  10.1107/S1600536809023423
PMCID: PMC2969328

Dichlorido[tris­(1H-benzimidazol-2-ylmeth­yl)amine-κ4 N,N 3,N 3′,N 3′′]iron(III) chloride tetra­hydro­furan monosolvate monohydrate

Abstract

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..

Related literature

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

An external file that holds a picture, illustration, etc.
Object name is e-65-0m828-scheme1.jpg

Experimental

Crystal data

  • [FeCl2(C24H21N7)]Cl·C4H8O·H2O
  • M r = 659.80
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m828-efi1.jpg
  • a = 10.2898 (4) Å
  • b = 13.7475 (5) Å
  • c = 21.5271 (7) Å
  • β = 101.614 (1)°
  • V = 2982.85 (19) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.81 mm−1
  • T = 292 K
  • 0.20 × 0.15 × 0.10 mm

Data collection

  • Bruker SMART APEX CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2001 [triangle]) T min = 0.844, T max = 0.923
  • 17337 measured reflections
  • 5527 independent reflections
  • 3999 reflections with I > 2σ(I)
  • R int = 0.046

Refinement

  • R[F 2 > 2σ(F 2)] = 0.047
  • wR(F 2) = 0.116
  • S = 1.00
  • 5527 reflections
  • 404 parameters
  • 21 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.33 e Å−3
  • Δρmin = −0.25 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809023423/ng2597sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809023423/ng2597Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

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).

Experimental

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

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).

Figures

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.
Fig. 2.
Plot of the crystal packing showing the linkage of the molecules by H-bonding shown as dashed lines.

Crystal data

[FeCl2(C24H21N7)]Cl·C4H8O·H2OF(000) = 1364
Mr = 659.80Dx = 1.469 Mg m3
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 mm1
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

Bruker SMART APEX CCD area-detector diffractometer5527 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

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 = 1.00w = 1/[σ2(Fo2) + (0.0587P)2] where P = (Fo2 + 2Fc2)/3
5527 reflections(Δ/σ)max < 0.001
404 parametersΔρmax = 0.33 e Å3
21 restraintsΔρmin = −0.25 e Å3

Special details

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)

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)

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, °)

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, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG2597).

References

  • Bruker (2001). SAINT-Plus, SMART and SADABS 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. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]

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