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Acta Crystallogr Sect E Struct Rep Online. 2010 June 1; 66(Pt 6): m711–m712.
Published online 2010 May 26. doi:  10.1107/S1600536810018787
PMCID: PMC2979518

[2,2′-(2,6,9,13-Tetra­azatetra­decane-1,14-di­yl)diphenolato]iron(III) iodide

Abstract

The title FeIII complex, [Fe(C22H32N4O2)]I, contains a six-coordinate FeN4O2 cation in which the ligand is a reduced Schiff base resulting from the NaBH4 reduction of the condensation product between salicylaldehyde and 1,5,8,12-tetra­azadodecane. In spite of the increased flexibility of the saturated backbone of the ligand compared to the Schiff base from which it was synthesized, the complex adopts a cis-FeN4O2 conformation for the phenolic O-atom donors, which contrasts with the trans conformation adopted by the analogous ClO4 salt [Yisgedu et al. (2009 [triangle]). J. Chem. Crystallogr. 39, 315–319]. In addition to extensive N—H(...)I hydrogen bonding between the amine H atoms and the anion there is a weak C—H(...)I inter­action.

Related literature

For early literature related to hexa­dentate ligands, see: Dwyer & Lions (1947 [triangle]); Das Sarma & Bailar (1955 [triangle]). For geometric changes from cis to trans, see: Bera et al. (2005 [triangle]); Boinnard et al. (1994 [triangle]); Dorbes et al. (2005 [triangle]); Floquet et al. (2004 [triangle]); Hayami et al. (1997 [triangle]); Ito et al. (1983 [triangle]); Maeda et al. (1991 [triangle]); McPartlin et al. (1978 [triangle]); Nishida et al. (1987 [triangle]); Salmon et al. (1999 [triangle]); Sinn et al. (1978 [triangle]). For complexes of reduced Schiff bases, see: Harpstrite et al. (2003 [triangle]). For the analogous ClO4 salt, see: Yisgedu et al. (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m711-scheme1.jpg

Experimental

Crystal data

  • [Fe(C22H32N4O2)]I
  • M r = 567.27
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m711-efi1.jpg
  • a = 9.3958 (1) Å
  • b = 13.0509 (1) Å
  • c = 19.4047 (3) Å
  • V = 2379.48 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.96 mm−1
  • T = 200 K
  • 0.51 × 0.47 × 0.39 mm

Data collection

  • Oxford Diffraction Gemini R diffractometer
  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 [triangle]) T min = 0.428, T max = 0.466
  • 43714 measured reflections
  • 9836 independent reflections
  • 7672 reflections with I > 2σ(I)
  • R int = 0.036

Refinement

  • R[F 2 > 2σ(F 2)] = 0.033
  • wR(F 2) = 0.066
  • S = 0.94
  • 9836 reflections
  • 271 parameters
  • H-atom parameters constrained
  • Δρmax = 1.32 e Å−3
  • Δρmin = −0.45 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 4113 Friedel pairs
  • Flack parameter: −0.018 (11)

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 [triangle]); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 [triangle]); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810018787/zl2278sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810018787/zl2278Isup2.hkl

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

Acknowledgments

RJB wishes to acknowledge the NSF–MRI program (grant CHE-0619278) for funds to purchase the diffractometer.

supplementary crystallographic information

Comment

Metal complexes of linear hexadentate ligands have fascinated inorganic chemists since their first report in 1947 (Dwyer & Lions, 1947). The first such report of an Fe complex of a linear FeN4O2 ligand derived from the Schiff base condensation of salicylaldehyde and triethylenetetraamine was in 1955 (Das Sarma & Bailar, 1955). However, this interest lapsed for several years until the discovery that such complexes exhibited spin-crossover magnetic behavior (Sinn et al., 1978). Hexadentate linear FeN4O2 ligands derived from the Schiff base condensation of salicylaldehyde and linear tetramines can be characterized by the number of linking carbon atoms in the tetramine backbone (from 222 to 333). The structures of Fe complexes of Sal222 (Sinn et al., 1978; Hayami et al., 1997; Floquet et al., 2004; Dorbes et al., 2005; Bera et al., 2005; Nishida et al., 1987; Salmon et al., 1999; McPartlin et al., 1978; Maeda et al., 1991; Boinnard et al., 1994), Sal232 (Hayami et al., 1997), Sal323 (Hayami et al., 1997; Ito, et al., 1983), and Sal333 (Ito, et al., 1983) derivatives have been reported. When chelating to Fe, as the number of carbon atoms in the tetramine backbone increases from 6 to 9, the conformation adopted by the ligand changes from a cis-FeN4O2 to a trans-FeN4O2 arrangement for the phenolic O donors. All structurally characterized Fe complexes with Sal222 have adopted the cis-FeN4O2 conformation while all those with either Sal323 or Sal333 have adopted the trans-FeN4O2 conformation. For Sal232, both conformations have been observed (Hayami et al., 1997). Further, it has been observed that, in addition to the usual reduction in metal ligand bond distances when going from high spin to low spin, the angles subtended at the Fe center reflect the magnetic properties of the compound (Hayami et al., 1997; Nishida et al., 1987) with low-spin compounds having such angles closer to 90° and 180°.

Despite the interest shown in salicylaldimine complexes with FeIII due to their interesting structural and magnetic properties, there have been very few structures reported on related complexes where the C=N imine groups have been reduced to C–N–H amine groups (Harpstrite et al., 2003; Yisgedu et al., 2009). One of these is the perchlorate analog of the title compound (Harpstrite et al., 2003). As expected, due to increased flexibility of the saturated amine, compared to the more rigid Schiff base, and also the length of the carbon backbone, this compound has adopted a trans-FeN4O2 conformation. To further characterize such compounds and determine the conformation adopted the structure of an FeIII complex of the iodide salt of reduced Sal323 is reported.

The title compound, [1,12-bis(2-hydroxybenzyl)-1,5,8,12-tetraazadodecane]iron(III) iodide, C22H32FeIN4O6, contains a six-coordinate FeN4O2 cation where the ligand (H2L) is the NaBH4 reduction product of the Schiff base resulting from the condensation of salicylaldehyde and 1,4,8,12-tetraazadodecane. In marked contrast to the perchlorate salt with the same 323 backbone, the title compound has adopted a cis FeN4O2 conformation. It is of interest to compare the metrical parameters of both the cis and trans structures with the same central Schiff base core. In the title compound, the Fe—O distances are shorter [1.8898 (13)/1.8999 (14) Å versus 1.9575 (10)/1.9142 (10) Å] while the Fe—N distances are longer [Fe—N average of 2.202 (1) Å versus 2.162 (1) Å]. Thus, even though they adopt different conformations, the bond distances and angles of both the perchlorate and iodide salts are more indicative of a high spin FeIII complex compared to the similar reduced 232 complex (Yisgedu et al., 2009).

In addition to extensive hydrogen bonding between the amine H atoms and the anion there is a weak C—H···I interaction (see table 1).

Experimental

Synthesis of ligand: The procedure for the synthesis of the ligand 1,12-bis(2-hydroxybenzyl)-1,4,8,12-tetraazaundecane (H2L) (Yisgedu et al., 2009) is as follows: A solution of 6.1 g (50 mmol) of salicylaldehyde in 10 ml ethanol was added drop-wise to a solution of 4.0 g (25 mmol) of 1,5,8,12-tetraazadodecane in 15 ml of ethanol. A deep yellow solution was obtained and was stirred for half an hour. To this yellow solution was added a NaBH4 solution (3.0 g NaBH4, 0.4 g NaOH, and 40 ml H2O). The volume of the solution was reduced to 20 ml and extracted with chloroform (3 x 40 ml). The extracts were combined and dried with Na2SO4. The Na2SO4 was filtered and the filtrate concentrated to a colorless thick oil (8.1 g, 87%).

Synthesis of [FeIIIL](ClO4): The synthesis of the above complex (Yisgedu et al., 2009) is as follows: To 0.85 g (2 mmol) of H2L dissolved in 10.0 ml of methanol was added 0.58 g (1 mmol) of Fe(ClO4)2.xH2O. The solution became violet and red-purple solids precipitated. This was stirred overnight, the solids filtered, washed with methanol and dried to give 1.65 g of red powder. Crystallization was effected by evaporation of a DMF solution of the complex (yield, 0.96 g, 67%).

Synthesis of [C22H32FeN4O2]I complex: A solution of 0.05 g (0.088 mmol) of the complex [FeIIIL]ClO4 was mixed with a solution of 10 % w/v aqueous solution of iodine and potassium iodide. 0.095 g of the aqueous solution of iodine/KI mixture in 5 ml methanol was mixed with the complex. The mixture was then stirred at room temperature for 24 hours. The solution was then evaporated, dissolved in DMF and filtered. The filtrate was layered with diethyl ether. After the diffusion process, brownish red crystals suitable for x-ray diffraction were obtained.

Figures

Fig. 1.
Diagram of C22H32FeIN4O6 showing atom labeling. Thermal ellipsoids are at the 50% probability level.
Fig. 2.
The molecular packing for C22H32FeIN4O6 viewed down the a axis. Hydrogen bonds are shown by dashed lines.

Crystal data

[Fe(C22H32N4O2)]IF(000) = 1148
Mr = 567.27Dx = 1.583 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 18399 reflections
a = 9.3958 (1) Åθ = 4.6–34.7°
b = 13.0509 (1) ŵ = 1.96 mm1
c = 19.4047 (3) ÅT = 200 K
V = 2379.48 (5) Å3Chunk, dark brown-red
Z = 40.51 × 0.47 × 0.39 mm

Data collection

Oxford Diffraction Gemini R diffractometer9836 independent reflections
Radiation source: fine-focus sealed tube7672 reflections with I > 2σ(I)
graphiteRint = 0.036
Detector resolution: 10.5081 pixels mm-1θmax = 34.8°, θmin = 4.7°
[var phi] and ω scansh = −14→14
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)k = −20→20
Tmin = 0.428, Tmax = 0.466l = −30→31
43714 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033H-atom parameters constrained
wR(F2) = 0.066w = 1/[σ2(Fo2) + (0.0354P)2] where P = (Fo2 + 2Fc2)/3
S = 0.94(Δ/σ)max = 0.001
9836 reflectionsΔρmax = 1.32 e Å3
271 parametersΔρmin = −0.45 e Å3
0 restraintsAbsolute structure: Flack (1983), 4113 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.018 (11)

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 > 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)

xyzUiso*/Ueq
I0.773383 (17)−0.160323 (12)0.264361 (9)0.04200 (5)
Fe0.82534 (3)0.15269 (2)0.131418 (12)0.01814 (5)
O1A0.79828 (16)0.08061 (11)0.04737 (7)0.0277 (3)
O1B0.71110 (15)0.26909 (10)0.11418 (7)0.0254 (3)
N1A0.64230 (16)0.07176 (12)0.17734 (8)0.0203 (3)
H1AA0.67630.01950.20540.024*
N2A0.86624 (18)0.20378 (12)0.23797 (9)0.0247 (3)
H2AA0.93440.25510.23420.030*
N1B1.01197 (16)0.23195 (12)0.09118 (8)0.0199 (3)
H1BA1.06390.25790.12810.024*
N2B0.97740 (18)0.03588 (13)0.16943 (9)0.0250 (3)
H2BA0.9218−0.02070.18050.030*
C1A0.7469 (2)−0.01336 (15)0.03747 (10)0.0243 (4)
C2A0.8057 (3)−0.07758 (19)−0.01269 (12)0.0385 (5)
H2AB0.8846−0.0551−0.03930.046*
C3A0.7485 (3)−0.17422 (19)−0.02343 (14)0.0450 (6)
H3AA0.7890−0.2178−0.05740.054*
C4A0.6331 (3)−0.20817 (18)0.01467 (13)0.0447 (6)
H4AA0.5944−0.27440.00680.054*
C5A0.5753 (3)−0.14535 (17)0.06366 (11)0.0352 (5)
H5AA0.4969−0.16910.09020.042*
C6A0.6286 (2)−0.04757 (15)0.07560 (10)0.0253 (4)
C7A0.5530 (2)0.02586 (16)0.12218 (10)0.0250 (4)
H7AA0.51300.08190.09380.030*
H7AB0.4722−0.01040.14400.030*
C8A0.5495 (2)0.14035 (17)0.21940 (11)0.0293 (4)
H8AA0.46210.10250.23220.035*
H8AB0.52060.19960.19080.035*
C9A0.6201 (3)0.17974 (17)0.28458 (11)0.0327 (5)
H9AA0.54730.21580.31240.039*
H9AB0.65300.12010.31170.039*
C10A0.7452 (2)0.25153 (15)0.27417 (10)0.0305 (4)
H10A0.71290.31180.24750.037*
H10B0.77800.27620.31970.037*
C11A0.9351 (3)0.12131 (18)0.27913 (12)0.0338 (5)
H11A0.86240.07160.29480.041*
H11B0.98140.15120.32030.041*
C1B0.74548 (19)0.36819 (14)0.10896 (9)0.0226 (4)
C2B0.6501 (2)0.44332 (17)0.13160 (11)0.0310 (4)
H2BB0.56320.42390.15290.037*
C3B0.6827 (3)0.54589 (17)0.12298 (12)0.0352 (5)
H3BA0.61610.59650.13710.042*
C4B0.8109 (2)0.57591 (16)0.09400 (12)0.0329 (5)
H4BA0.83260.64660.08870.040*
C5B0.9073 (2)0.50167 (15)0.07286 (11)0.0273 (4)
H5BA0.99630.52190.05400.033*
C6B0.8749 (2)0.39720 (14)0.07890 (10)0.0216 (4)
C7B0.9688 (2)0.31914 (15)0.04574 (10)0.0247 (4)
H7BA1.05600.35390.02910.030*
H7BB0.91890.29100.00500.030*
C8B1.1072 (2)0.16359 (18)0.04945 (10)0.0285 (4)
H8BA1.18040.20630.02660.034*
H8BB1.04980.13060.01290.034*
C9B1.1806 (2)0.08143 (18)0.09064 (12)0.0332 (5)
H9BA1.23070.11420.12970.040*
H9BB1.25340.04870.06110.040*
C10B1.0824 (2)−0.00223 (16)0.11913 (12)0.0315 (5)
H10C1.0311−0.03470.08030.038*
H10D1.1413−0.05570.14140.038*
C11B1.0443 (2)0.06764 (17)0.23547 (12)0.0322 (4)
H11C1.12520.11430.22620.039*
H11D1.08100.00670.26010.039*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
I0.03535 (8)0.03358 (7)0.05708 (10)−0.00127 (7)−0.00778 (7)0.01797 (7)
Fe0.01560 (10)0.02019 (11)0.01862 (11)0.00004 (10)0.00055 (9)0.00102 (10)
O1A0.0264 (8)0.0351 (7)0.0216 (7)−0.0061 (6)0.0031 (5)−0.0040 (5)
O1B0.0174 (6)0.0267 (6)0.0321 (7)0.0016 (5)0.0029 (5)0.0081 (5)
N1A0.0186 (7)0.0219 (7)0.0203 (7)−0.0002 (6)0.0024 (6)0.0010 (6)
N2A0.0264 (8)0.0245 (7)0.0233 (8)−0.0040 (6)−0.0009 (7)0.0012 (6)
N1B0.0131 (7)0.0245 (7)0.0219 (7)0.0000 (6)0.0008 (6)0.0021 (6)
N2B0.0220 (8)0.0217 (7)0.0314 (9)−0.0003 (6)−0.0027 (7)0.0021 (6)
C1A0.0229 (10)0.0284 (9)0.0215 (8)0.0018 (7)−0.0041 (7)−0.0035 (7)
C2A0.0375 (13)0.0475 (13)0.0305 (11)0.0073 (10)−0.0024 (9)−0.0118 (9)
C3A0.0488 (16)0.0396 (12)0.0466 (13)0.0141 (11)−0.0102 (11)−0.0189 (10)
C4A0.0655 (18)0.0248 (10)0.0439 (14)0.0010 (11)−0.0180 (13)−0.0027 (9)
C5A0.0441 (13)0.0296 (11)0.0318 (11)−0.0085 (10)−0.0093 (9)0.0050 (9)
C6A0.0268 (10)0.0275 (9)0.0217 (9)−0.0018 (8)−0.0071 (7)0.0017 (7)
C7A0.0169 (8)0.0316 (9)0.0264 (10)−0.0027 (7)0.0000 (7)0.0002 (7)
C8A0.0231 (9)0.0333 (11)0.0314 (10)0.0005 (8)0.0099 (7)−0.0013 (8)
C9A0.0370 (12)0.0345 (11)0.0267 (10)−0.0021 (9)0.0115 (8)−0.0040 (8)
C10A0.0400 (13)0.0268 (9)0.0246 (9)−0.0037 (8)0.0064 (8)−0.0060 (7)
C11A0.0376 (12)0.0371 (11)0.0267 (11)−0.0007 (9)−0.0071 (9)0.0059 (8)
C1B0.0217 (10)0.0257 (8)0.0204 (8)0.0031 (6)−0.0008 (6)0.0043 (6)
C2B0.0251 (10)0.0347 (10)0.0331 (10)0.0072 (8)0.0044 (9)0.0054 (9)
C3B0.0404 (12)0.0304 (10)0.0350 (12)0.0141 (9)−0.0024 (10)−0.0017 (9)
C4B0.0372 (13)0.0243 (9)0.0373 (12)0.0035 (9)−0.0072 (9)0.0026 (8)
C5B0.0262 (10)0.0298 (10)0.0260 (10)−0.0022 (8)−0.0030 (8)0.0049 (8)
C6B0.0206 (9)0.0242 (8)0.0201 (9)0.0007 (7)−0.0009 (7)0.0041 (7)
C7B0.0211 (9)0.0297 (10)0.0233 (9)0.0015 (7)0.0028 (7)0.0083 (7)
C8B0.0195 (8)0.0346 (10)0.0315 (10)0.0057 (9)0.0086 (7)0.0007 (9)
C9B0.0188 (9)0.0382 (11)0.0427 (13)0.0100 (9)0.0023 (9)−0.0006 (9)
C10B0.0285 (11)0.0273 (10)0.0388 (12)0.0089 (8)−0.0002 (9)0.0005 (8)
C11B0.0325 (11)0.0343 (10)0.0296 (11)0.0014 (8)−0.0115 (9)0.0047 (9)

Geometric parameters (Å, °)

Fe—O1B1.8898 (13)C8A—H8AA0.9900
Fe—O1A1.8999 (14)C8A—H8AB0.9900
Fe—N1B2.1805 (15)C9A—C10A1.517 (3)
Fe—N1A2.2062 (15)C9A—H9AA0.9900
Fe—N2A2.2062 (17)C9A—H9AB0.9900
Fe—N2B2.2158 (17)C10A—H10A0.9900
O1A—C1A1.332 (2)C10A—H10B0.9900
O1B—C1B1.337 (2)C11A—C11B1.504 (3)
N1A—C7A1.486 (2)C11A—H11A0.9900
N1A—C8A1.493 (2)C11A—H11B0.9900
N1A—H1AA0.9300C1B—C2B1.399 (3)
N2A—C10A1.475 (3)C1B—C6B1.401 (3)
N2A—C11A1.488 (3)C2B—C3B1.383 (3)
N2A—H2AA0.9300C2B—H2BB0.9500
N1B—C7B1.496 (2)C3B—C4B1.386 (3)
N1B—C8B1.501 (2)C3B—H3BA0.9500
N1B—H1BA0.9300C4B—C5B1.388 (3)
N2B—C10B1.474 (3)C4B—H4BA0.9500
N2B—C11B1.486 (3)C5B—C6B1.402 (3)
N2B—H2BA0.9300C5B—H5BA0.9500
C1A—C2A1.398 (3)C6B—C7B1.493 (3)
C1A—C6A1.408 (3)C7B—H7BA0.9900
C2A—C3A1.387 (3)C7B—H7BB0.9900
C2A—H2AB0.9500C8B—C9B1.505 (3)
C3A—C4A1.385 (4)C8B—H8BA0.9900
C3A—H3AA0.9500C8B—H8BB0.9900
C4A—C5A1.368 (4)C9B—C10B1.533 (3)
C4A—H4AA0.9500C9B—H9BA0.9900
C5A—C6A1.390 (3)C9B—H9BB0.9900
C5A—H5AA0.9500C10B—H10C0.9900
C6A—C7A1.497 (3)C10B—H10D0.9900
C7A—H7AA0.9900C11B—H11C0.9900
C7A—H7AB0.9900C11B—H11D0.9900
C8A—C9A1.518 (3)
O1B—Fe—O1A99.79 (6)C9A—C8A—H8AB108.8
O1B—Fe—N1B90.69 (6)H8AA—C8A—H8AB107.7
O1A—Fe—N1B92.02 (6)C10A—C9A—C8A115.90 (17)
O1B—Fe—N1A90.78 (6)C10A—C9A—H9AA108.3
O1A—Fe—N1A90.31 (6)C8A—C9A—H9AA108.3
N1B—Fe—N1A177.01 (6)C10A—C9A—H9AB108.3
O1B—Fe—N2A91.25 (6)C8A—C9A—H9AB108.3
O1A—Fe—N2A167.81 (6)H9AA—C9A—H9AB107.4
N1B—Fe—N2A92.99 (6)N2A—C10A—C9A113.59 (16)
N1A—Fe—N2A84.37 (6)N2A—C10A—H10A108.8
O1B—Fe—N2B168.01 (6)C9A—C10A—H10A108.8
O1A—Fe—N2B91.80 (6)N2A—C10A—H10B108.8
N1B—Fe—N2B85.82 (6)C9A—C10A—H10B108.8
N1A—Fe—N2B92.22 (6)H10A—C10A—H10B107.7
N2A—Fe—N2B77.50 (6)N2A—C11A—C11B109.34 (17)
C1A—O1A—Fe128.92 (12)N2A—C11A—H11A109.8
C1B—O1B—Fe130.83 (12)C11B—C11A—H11A109.8
C7A—N1A—C8A107.79 (15)N2A—C11A—H11B109.8
C7A—N1A—Fe110.01 (11)C11B—C11A—H11B109.8
C8A—N1A—Fe112.91 (12)H11A—C11A—H11B108.3
C7A—N1A—H1AA108.7O1B—C1B—C2B119.97 (17)
C8A—N1A—H1AA108.7O1B—C1B—C6B120.18 (16)
Fe—N1A—H1AA108.7C2B—C1B—C6B119.82 (17)
C10A—N2A—C11A112.66 (17)C3B—C2B—C1B119.9 (2)
C10A—N2A—Fe116.09 (13)C3B—C2B—H2BB120.0
C11A—N2A—Fe111.11 (13)C1B—C2B—H2BB120.0
C10A—N2A—H2AA105.3C2B—C3B—C4B121.0 (2)
C11A—N2A—H2AA105.3C2B—C3B—H3BA119.5
Fe—N2A—H2AA105.3C4B—C3B—H3BA119.5
C7B—N1B—C8B107.20 (15)C3B—C4B—C5B119.31 (19)
C7B—N1B—Fe110.74 (11)C3B—C4B—H4BA120.3
C8B—N1B—Fe112.99 (12)C5B—C4B—H4BA120.3
C7B—N1B—H1BA108.6C4B—C5B—C6B120.9 (2)
C8B—N1B—H1BA108.6C4B—C5B—H5BA119.6
Fe—N1B—H1BA108.6C6B—C5B—H5BA119.6
C10B—N2B—C11B112.46 (17)C1B—C6B—C5B119.06 (18)
C10B—N2B—Fe116.31 (13)C1B—C6B—C7B120.53 (17)
C11B—N2B—Fe111.58 (12)C5B—C6B—C7B119.96 (18)
C10B—N2B—H2BA105.1C6B—C7B—N1B115.16 (15)
C11B—N2B—H2BA105.1C6B—C7B—H7BA108.5
Fe—N2B—H2BA105.1N1B—C7B—H7BA108.5
O1A—C1A—C2A120.62 (19)C6B—C7B—H7BB108.5
O1A—C1A—C6A120.15 (17)N1B—C7B—H7BB108.5
C2A—C1A—C6A119.18 (19)H7BA—C7B—H7BB107.5
C3A—C2A—C1A119.8 (2)N1B—C8B—C9B114.22 (16)
C3A—C2A—H2AB120.1N1B—C8B—H8BA108.7
C1A—C2A—H2AB120.1C9B—C8B—H8BA108.7
C4A—C3A—C2A120.9 (2)N1B—C8B—H8BB108.7
C4A—C3A—H3AA119.5C9B—C8B—H8BB108.7
C2A—C3A—H3AA119.5H8BA—C8B—H8BB107.6
C5A—C4A—C3A119.3 (2)C8B—C9B—C10B115.07 (18)
C5A—C4A—H4AA120.3C8B—C9B—H9BA108.5
C3A—C4A—H4AA120.3C10B—C9B—H9BA108.5
C4A—C5A—C6A121.5 (2)C8B—C9B—H9BB108.5
C4A—C5A—H5AA119.2C10B—C9B—H9BB108.5
C6A—C5A—H5AA119.2H9BA—C9B—H9BB107.5
C5A—C6A—C1A119.21 (19)N2B—C10B—C9B113.66 (17)
C5A—C6A—C7A121.14 (19)N2B—C10B—H10C108.8
C1A—C6A—C7A119.29 (17)C9B—C10B—H10C108.8
N1A—C7A—C6A115.14 (16)N2B—C10B—H10D108.8
N1A—C7A—H7AA108.5C9B—C10B—H10D108.8
C6A—C7A—H7AA108.5H10C—C10B—H10D107.7
N1A—C7A—H7AB108.5N2B—C11B—C11A109.10 (17)
C6A—C7A—H7AB108.5N2B—C11B—H11C109.9
H7AA—C7A—H7AB107.5C11A—C11B—H11C109.9
N1A—C8A—C9A113.79 (17)N2B—C11B—H11D109.9
N1A—C8A—H8AA108.8C11A—C11B—H11D109.9
C9A—C8A—H8AA108.8H11C—C11B—H11D108.3
N1A—C8A—H8AB108.8
O1B—Fe—O1A—C1A−121.63 (16)C6A—C1A—C2A—C3A−1.0 (3)
N1B—Fe—O1A—C1A147.32 (16)C1A—C2A—C3A—C4A0.3 (4)
N1A—Fe—O1A—C1A−30.79 (16)C2A—C3A—C4A—C5A−0.2 (4)
N2A—Fe—O1A—C1A33.1 (4)C3A—C4A—C5A—C6A0.8 (4)
N2B—Fe—O1A—C1A61.45 (16)C4A—C5A—C6A—C1A−1.5 (3)
O1A—Fe—O1B—C1B−116.70 (15)C4A—C5A—C6A—C7A171.5 (2)
N1B—Fe—O1B—C1B−24.54 (15)O1A—C1A—C6A—C5A178.97 (18)
N1A—Fe—O1B—C1B152.85 (15)C2A—C1A—C6A—C5A1.6 (3)
N2A—Fe—O1B—C1B68.47 (16)O1A—C1A—C6A—C7A5.8 (3)
N2B—Fe—O1B—C1B48.3 (4)C2A—C1A—C6A—C7A−171.55 (19)
O1B—Fe—N1A—C7A82.12 (12)C8A—N1A—C7A—C6A−178.68 (16)
O1A—Fe—N1A—C7A−17.68 (12)Fe—N1A—C7A—C6A57.82 (18)
N2A—Fe—N1A—C7A173.30 (13)C5A—C6A—C7A—N1A127.69 (19)
N2B—Fe—N1A—C7A−109.49 (12)C1A—C6A—C7A—N1A−59.3 (2)
O1B—Fe—N1A—C8A−38.34 (13)C7A—N1A—C8A—C9A170.82 (17)
O1A—Fe—N1A—C8A−138.14 (13)Fe—N1A—C8A—C9A−67.46 (19)
N2A—Fe—N1A—C8A52.85 (13)N1A—C8A—C9A—C10A66.2 (2)
N2B—Fe—N1A—C8A130.06 (13)C11A—N2A—C10A—C9A−66.6 (2)
O1B—Fe—N2A—C10A38.47 (13)Fe—N2A—C10A—C9A63.1 (2)
O1A—Fe—N2A—C10A−116.6 (3)C8A—C9A—C10A—N2A−62.7 (3)
N1B—Fe—N2A—C10A129.23 (13)C10A—N2A—C11A—C11B172.73 (16)
N1A—Fe—N2A—C10A−52.18 (13)Fe—N2A—C11A—C11B40.5 (2)
N2B—Fe—N2A—C10A−145.72 (14)Fe—O1B—C1B—C2B−146.23 (16)
O1B—Fe—N2A—C11A168.93 (14)Fe—O1B—C1B—C6B35.7 (2)
O1A—Fe—N2A—C11A13.8 (4)O1B—C1B—C2B—C3B−176.72 (19)
N1B—Fe—N2A—C11A−100.31 (14)C6B—C1B—C2B—C3B1.3 (3)
N1A—Fe—N2A—C11A78.27 (14)C1B—C2B—C3B—C4B−2.0 (3)
N2B—Fe—N2A—C11A−15.27 (14)C2B—C3B—C4B—C5B0.6 (3)
O1B—Fe—N1B—C7B−20.81 (13)C3B—C4B—C5B—C6B1.6 (3)
O1A—Fe—N1B—C7B79.02 (13)O1B—C1B—C6B—C5B178.81 (17)
N2A—Fe—N1B—C7B−112.10 (12)C2B—C1B—C6B—C5B0.8 (3)
N2B—Fe—N1B—C7B170.67 (13)O1B—C1B—C6B—C7B6.5 (3)
O1B—Fe—N1B—C8B−141.09 (13)C2B—C1B—C6B—C7B−171.54 (18)
O1A—Fe—N1B—C8B−41.26 (13)C4B—C5B—C6B—C1B−2.2 (3)
N2A—Fe—N1B—C8B127.62 (12)C4B—C5B—C6B—C7B170.12 (19)
N2B—Fe—N1B—C8B50.39 (13)C1B—C6B—C7B—N1B−56.4 (2)
O1B—Fe—N2B—C10B−122.7 (3)C5B—C6B—C7B—N1B131.38 (19)
O1A—Fe—N2B—C10B42.58 (14)C8B—N1B—C7B—C6B−178.95 (16)
N1B—Fe—N2B—C10B−49.31 (14)Fe—N1B—C7B—C6B57.38 (19)
N1A—Fe—N2B—C10B132.95 (14)C7B—N1B—C8B—C9B170.13 (18)
N2A—Fe—N2B—C10B−143.31 (15)Fe—N1B—C8B—C9B−67.59 (19)
O1B—Fe—N2B—C11B8.1 (4)N1B—C8B—C9B—C10B68.4 (2)
O1A—Fe—N2B—C11B173.41 (14)C11B—N2B—C10B—C9B−69.6 (2)
N1B—Fe—N2B—C11B81.52 (14)Fe—N2B—C10B—C9B60.8 (2)
N1A—Fe—N2B—C11B−96.21 (13)C8B—C9B—C10B—N2B−63.9 (3)
N2A—Fe—N2B—C11B−12.48 (13)C10B—N2B—C11B—C11A170.70 (16)
Fe—O1A—C1A—C2A−141.17 (18)Fe—N2B—C11B—C11A37.91 (19)
Fe—O1A—C1A—C6A41.5 (2)N2A—C11A—C11B—N2B−51.6 (2)
O1A—C1A—C2A—C3A−178.4 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1A—H1AA···I0.932.773.6800 (16)168
N2A—H2AA···Ii0.932.963.8227 (17)155
N1B—H1BA···Ii0.932.803.7285 (16)178
N2B—H2BA···I0.932.813.6911 (17)158
C11B—H11C···Ii0.993.103.942 (2)144

Symmetry codes: (i) −x+2, y+1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZL2278).

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