Download citation
Download citation
link to html
The title compound, tris­[2-(4,5-dihydrooxazol-2-yl-κN)phenolato-κO]­iron(III), [Fe(C9H8NO2)3], is disordered over a non-crystallographic twofold rotation axis perpendicular to the crystallographic threefold rotation axis. The disorder can be a pure rotational disorder of an iron complex in the facial configuration, or the consequence of a mixture of facial and meridional configurations. In the latter case, at least 25% of the iron complexes must adopt the facial configuration in order to obtain the disorder ratio observed in the crystal.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270102009435/fg1649sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270102009435/fg1649Isup2.hkl
Contains datablock I

CCDC reference: 192946

Comment top

The title compound, (I), was prepared in the course of our investigation aimed at producing new epoxidation catalysts (Hoogenraad et al., 2002). The crystal structure, abbreviated as [Fe(phox)3], shows the FeIII ion located on a crystallographic threefold rotation axis. The distribution of the FeIII ions over the unit cell follows space group P3m1, which is a supergroup of P3, the actual space group of (I). The higher symmetry only holds for the iron substructure.

The phox ligand is found to be disordered over two orientations, hereafter indicated by A [occupancy factor refined to 0.758 (5)] and B [occupancy factor 0.242 (5)]. Orientations A and B are related by a non-crystallographic twofold rotation axis perpendicular to the crystallographic threefold rotation axis. In Fig. 1, a displacement ellipsoid plot of the major component is given. Fig. 2 shows both orientations of the ligand in ball-and-stick model.

The crystal packing can accommodate both orientations of the ligand in the ratio found during refinement. Only when the contact ligands of two neighbouring complexes are in the minor disorder component orientations (B), interatomic distances that are shorter than the Van der Waals radii are found.

Exact analysis of the configuration of the coordinating phox ligands to the central cation is very difficult due to the presence of disorder in the crystal structure. We expected Fe(phox)3 to assume the meridional configuration, as all other previous reported FeIIIN3O3 species [Cambridge Structural Database (CSD), February 2002 update; Allen & Kennard, 1993; the only exception to found is the mixed valence FeII/FeIII complex reported by Mashuta et al., 1992) and as the related manganese(III) complex Mn(phox)3 (Hoogenraad et al., 1998). A complex in the meridional configuration would have its three phox ligands in an AAB orientation. The threefold crystallographic symmetry would generate the permutations ABA and BAA, resulting in an occupancy of 2/3 for the major component. However, the Fe(phox)3 complex as a whole can also be rotated by the local twofold axis that causes the disorder, resulting in the BBA orientation of the ligands (and permutations thereof). The observed occupation factor of component A could therefore lie between the values 2/3 and 1/3, depending on the amount of disorder of the complete molecule over the local twofold rotation axis.

The observed value of 0.758 (5) for the occupancy of A clearly lies outside of the expected range. If this is not an artifact caused by effects unaccounted for in the present model [FOOTNOTE: There is no indication of twinning over one of the symmetry elements of the supergroup of the iron substructure, as is illustrated by the averaging index Rint, which amounts to 0.359 for P3m1 as opposed to 0.057 for P3. Systematic deviations of Fcalc from Fobs, another indicator of twinning, were not found.], the high value found for the occupancy of the major component would suggest that at least a fraction of 0.25 of the molecules has its three ligands in the AAA (or BBB) configuration. AAA represents a structure with facial configuration of the ligands. The disorder model can also be interpreted as consisting of 75.8% AAA configuration and 24.2% BBB configuration, i.e. 100% facial configuration distributed over two orientations which are related by the disorder operation. It should be noted that according to the CSD, the facial configuration only occurs if the ligands are forced by covalent or coordinating bonds to adopt this orientation. Since the facial configuration has not been corroborated with other techniques, further study is necessary to unequivocally assign this configuration to a part of the complex molecules present in the crystal.

The Cremer & Pople (1975) total puckering amplitude amounts to 0.077 (9) Å for the oxazolinyl ring and to 0.020 (10) Å for the phenyl ring of the major disorder component, indicating that the former ring deviates slightly more from planarity than the latter. For the minor disorder component, the puckering parameters are 0.05 (2) and 0.03 (3) for the oxazolinyl and phenyl rings, respectively, showing a less pronounced difference. The acute angle between the least-squares planes through the oxazolinyl and phenyl rings amounts to 6.1 (4) and 3.0 (12)° for the major and the minor disorder components, respectively. The six-membered chelate rings deviate significantly from planarity, as is indicated by a total puckering amplitude of 0.167 (6) Å for the major disorder component and 0.263 (18) Å for the minor disorder component.

The crystal structure displays a close C—H···O contact for each disorder component. Geometry details are given in Table 2. These interactions link the molecules into infinite chains parallel to c. An illustration is given in Fig. 3.

In the IR spectrum of [Fe(phox)3] the effect of complexation on the CN bond is demonstrated by the shift from 1644 cm-1 in the free ligand to 1617 cm-1 in the complex. The UV–vis–NIR spectrum of the solid compound shows a broad absorption in the range between 700 and 230 nm. The UV–vis–NIR spectrum of [Fe(phox)3] in a methanol solution shows an absorption band at 461 nm, which can be assigned to the phenolate to FeIII ligand to metal charge transfer (LMCT) band. Bands observed at 307 and 222 nm, which are also present in the free ligand, can be assigned to π π* transitions of the ligand. The magnetic moment of [Fe(phox)3] (5.70 µB) is close to the spin-only value of 5.92µB expected for an S = 5/2 system of an octahedral high-spin FeIII ion. During variable temperature measurements, the compound shows a strict Curie–Weiss behaviour, indicating an isolated paramagnetic ion as the plot of 1/χ against T can be extrapolated to zero.

Experimental top

For the synthesis of [Fe(phox)3], FeCl3·6H2O (0.27 g, 1.0 mmol) dissolved in water (10 ml) was added to a stirred solution of Hphox (0.49 g, 3.0 mmol) and triethylamine (0.30 g, 3.0 mmol) in methanol (10 ml). A dark-red product precipitated within a number of days and was collected by filtration. The complex was recrystallized from acetonitrile to yield 0.40 g (0.74 mmol, 74%) of [Fe(phox)3]. X-ray quality crystals were obtained after recrystallization from MeOH/MeCN (3:1). IR (cm-1): 1617 (s), 1589 (w), 1545 (m), 1470 (s), 1441 (m), 1390 (m), 1336 (m), 1260 (m), 1239 (m), 1154 (m), 1071 (m), 947 (w), 928 (w), 856 (m), 759 (m), 688 (m), 660 (w), 601 (w). Analysis calculated for C27H24FeN3O6: C 59.80, H 4.46, N 7,75%; found: C 59.38, H 4.63, N 7.75%. ES—MS: m/z: 543 ([Fe(phox)3]+H+), 380 ([Fe(phox)2]+), 164 (Hphox+H+). Electronic absorption spectrum in MeOH, λmax/nm (ε/M-1 × cm-1) 461 (4.1 × 103), 307 (1.4 × 104), 222 (5.1 × 104). µeff = 5.70µB (at 290.6 K).

Refinement top

The phox ligand was found to be disordered over two positions, related by a non-crystallographic twofold rotation axis. The smallest angle of the disorder axis to a translation axis is approximately 9°. The coordinates of both components and their occupation ratio were refined. Corresponding distances and 1–3 distances of the disorder components were restrained to be equal within an s.u. of 0.02 Å. H atoms were included in the model on calculated positions, riding on their carrier atoms. The minor component non-H atoms were refined with an isotropic displacement parameter. The isotropic displacement parameters of H atoms bonded to C atoms were coupled to the equivalent isotropic displacement parameter of their carrier atoms by a fixed factor of 1.2.

Computing details top

Data collection: locally modified CAD-4 Software (Enraf-Nonius, 1989); cell refinement: SET4 (de Boer & Duisenberg, 1984); data reduction: HELENA (Spek, 1997); program(s) used to solve structure: SHELXS86 (Sheldrick, 1985); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2002); software used to prepare material for publication: PLATON.

Figures top
[Figure 1] Fig. 1. View of [Fe(phox)3] with the atom-numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level. The minor disorder component has been omitted for clarity. The labels for the minor disorder component are obtained by replacing the first digit of the atom label by "2". [Symmetry codes: (i) 1 - y, x-y, z; (ii) 1 - x + y, 1 - x, z.]
[Figure 2] Fig. 2. The major (solid lines) and minor (dashed lines) disorder components of [Fe(phox)3], which are related by a non-crystallographic twofold rotation axis. H atoms have been omitted for clarity.
[Figure 3] Fig. 3. The C—H···O interactions in [Fe(phox)3]. H atoms, with the exception of the CH2 moiety involved in the interaction, have been omitted for clarity. Only the major disorder component is shown.
Tris[2-(2'-oxazolinyl)-phenolato]iron(II) top
Crystal data top
[Fe(C9H8NO2)3]Least Squares Treatment of 25 SET4 setting angles.
Mr = 542.34Dx = 1.466 Mg m3
Trigonal, P3Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 3Cell parameters from 25 reflections
a = 14.882 (2) Åθ = 10.2–15.3°
c = 6.4052 (11) ŵ = 0.66 mm1
V = 1228.5 (3) Å3T = 150 K
Z = 2Block, dark red
F(000) = 5620.30 × 0.15 × 0.05 mm
Data collection top
Enraf-Nonius CAD-4 Turbo
diffractometer
Rint = 0.057
Radiation source: Rotating Anodeθmax = 25.0°, θmin = 1.6°
Graphite monochromatorh = 1917
ω scans with Δω = 1.26+0.35 tan θk = 1719
1686 measured reflectionsl = 80
1448 independent reflections3 standard reflections every 60 min
970 reflections with I > 2σ(I) intensity decay: 3%
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)] = 0.074Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.168H-atom parameters not refined
S = 1.19 w = 1/[σ2(Fo2) + (0.0615P)2 + 1.78P]
where P = (Fo2 + 2Fc2)/3
1448 reflections(Δ/σ)max < 0.001
161 parametersΔρmax = 0.51 e Å3
31 restraintsΔρmin = 0.53 e Å3
Crystal data top
[Fe(C9H8NO2)3]Z = 2
Mr = 542.34Mo Kα radiation
Trigonal, P3µ = 0.66 mm1
a = 14.882 (2) ÅT = 150 K
c = 6.4052 (11) Å0.30 × 0.15 × 0.05 mm
V = 1228.5 (3) Å3
Data collection top
Enraf-Nonius CAD-4 Turbo
diffractometer
Rint = 0.057
1686 measured reflections3 standard reflections every 60 min
1448 independent reflections intensity decay: 3%
970 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.07431 restraints
wR(F2) = 0.168H-atom parameters not refined
S = 1.19Δρmax = 0.51 e Å3
1448 reflectionsΔρmin = 0.53 e Å3
161 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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)
Fe10.666670.333330.6262 (2)0.0197 (3)
O110.5362 (4)0.2853 (5)0.7719 (9)0.038 (2)0.758 (5)
O120.4886 (4)0.4313 (5)0.2576 (8)0.0422 (19)0.758 (5)
N110.6037 (5)0.3974 (5)0.4131 (10)0.026 (2)0.758 (5)
C110.4433 (6)0.2738 (6)0.7262 (13)0.029 (3)0.758 (5)
C120.3603 (6)0.2190 (7)0.8634 (14)0.046 (3)0.758 (5)
C130.2650 (6)0.2047 (7)0.8198 (15)0.052 (3)0.758 (5)
C140.2473 (6)0.2461 (7)0.6441 (15)0.049 (3)0.758 (5)
C150.3269 (7)0.3022 (7)0.5106 (13)0.043 (3)0.758 (5)
C160.4262 (5)0.3181 (6)0.5502 (11)0.027 (3)0.758 (5)
C170.5089 (6)0.3822 (6)0.4104 (11)0.029 (3)0.758 (5)
C180.6614 (6)0.4711 (7)0.2434 (12)0.039 (3)0.758 (5)
C190.5807 (6)0.4849 (6)0.1292 (11)0.038 (3)0.758 (5)
C250.3080 (15)0.2456 (17)0.640 (3)0.032 (6)*0.242 (5)
C260.4148 (15)0.278 (2)0.648 (4)0.039 (9)*0.242 (5)
C270.4501 (14)0.2350 (17)0.808 (3)0.029 (6)*0.242 (5)
C280.5430 (13)0.1883 (16)1.012 (3)0.027 (5)*0.242 (5)
C290.4328 (14)0.1337 (16)1.082 (3)0.027 (5)*0.242 (5)
C220.4453 (16)0.3961 (18)0.370 (4)0.035 (6)*0.242 (5)
C230.3417 (16)0.3622 (19)0.361 (3)0.044 (7)*0.242 (5)
C240.2745 (18)0.287 (2)0.491 (4)0.051 (9)*0.242 (5)
O210.5853 (11)0.3846 (13)0.513 (3)0.027 (5)*0.242 (5)
O220.3783 (11)0.1634 (12)0.938 (2)0.035 (4)*0.242 (5)
N210.5443 (14)0.2542 (16)0.839 (3)0.037 (7)*0.242 (5)
C210.4833 (14)0.3543 (16)0.515 (3)0.017 (5)*0.242 (5)
H18B0.716300.538000.300600.0470*0.758 (5)
H19A0.602600.559400.115900.0460*0.758 (5)
H19B0.568200.453800.012000.0460*0.758 (5)
H120.371000.191400.988700.0560*0.758 (5)
H130.209200.165200.913000.0630*0.758 (5)
H140.180000.235600.615900.0580*0.758 (5)
H150.315000.331000.388600.0520*0.758 (5)
H18A0.693700.442500.149400.0470*0.758 (5)
H220.491600.448400.276600.0420*0.242 (5)
H230.316400.391600.261500.0530*0.242 (5)
H240.202400.263200.478900.0610*0.242 (5)
H250.260600.196000.736200.0380*0.242 (5)
H28A0.590100.230701.125600.0330*0.242 (5)
H28B0.563800.138200.962700.0330*0.242 (5)
H29A0.403700.057601.079900.0330*0.242 (5)
H29B0.427300.155001.225800.0330*0.242 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0173 (5)0.0173 (5)0.0244 (7)0.0086 (2)0.00000.0000
O110.026 (3)0.060 (4)0.043 (4)0.032 (3)0.009 (2)0.021 (3)
O120.044 (3)0.061 (4)0.040 (3)0.040 (3)0.001 (3)0.017 (3)
N110.025 (4)0.032 (4)0.024 (4)0.017 (3)0.004 (3)0.009 (3)
C110.025 (4)0.032 (5)0.032 (5)0.015 (4)0.006 (4)0.007 (4)
C120.032 (5)0.058 (6)0.058 (6)0.029 (4)0.009 (4)0.021 (5)
C130.025 (5)0.045 (6)0.081 (7)0.014 (4)0.005 (4)0.014 (5)
C140.013 (4)0.057 (6)0.082 (7)0.022 (4)0.002 (4)0.003 (5)
C150.036 (6)0.058 (6)0.043 (5)0.029 (5)0.010 (4)0.001 (4)
C160.015 (4)0.034 (5)0.030 (4)0.010 (4)0.001 (3)0.004 (4)
C170.037 (5)0.040 (5)0.024 (4)0.029 (4)0.001 (4)0.004 (4)
C180.042 (5)0.048 (5)0.038 (5)0.031 (4)0.018 (4)0.023 (4)
C190.052 (5)0.044 (5)0.030 (4)0.032 (4)0.007 (4)0.010 (4)
Geometric parameters (Å, º) top
Fe1—O111.940 (7)C21—C261.38 (3)
Fe1—N112.132 (7)C22—C231.36 (4)
Fe1—O211.870 (19)C23—C241.35 (3)
Fe1—N212.10 (2)C24—C251.36 (4)
O11—C111.338 (12)C25—C261.41 (4)
O12—C171.343 (10)C26—C271.44 (3)
O12—C191.448 (11)C28—C291.49 (3)
O21—C211.35 (3)C12—H120.9506
O22—C271.35 (3)C13—H130.9505
O22—C291.44 (3)C14—H140.9506
N11—C171.313 (13)C15—H150.9495
N11—C181.476 (11)C18—H18A0.9896
N21—C271.30 (3)C18—H18B0.9897
N21—C281.47 (3)C19—H19A0.9906
C11—C121.398 (13)C19—H19B0.9903
C11—C161.392 (11)C22—H220.9498
C12—C131.354 (15)C23—H230.9508
C13—C141.370 (14)C24—H240.9501
C14—C151.357 (14)C25—H250.9494
C15—C161.398 (14)C28—H28A0.9882
C16—C171.433 (11)C28—H28B0.9911
C18—C191.505 (14)C29—H29A0.9899
C21—C221.39 (3)C29—H29B0.9907
Fe1···C26i3.41 (2)C17···H18Aix2.9204
Fe1···C27i3.028 (18)C18···H18Aix2.8988
Fe1···C17i3.108 (10)C18···H12iv2.8674
Fe1···C18i3.222 (11)C19···H19Avi2.9227
Fe1···C21i2.98 (2)C19···H19Bvi2.8858
Fe1···C28i3.19 (2)C21···H22x3.0734
Fe1···H18Ai3.3874C22···H22x3.0312
Fe1···H18Bi3.4529C23···H29Axi2.8845
Fe1···H28Aii3.4889C24···H29Bxii2.7784
Fe1···H28Aiii3.4889C25···H24vii2.5989
Fe1···H28Aiv3.4889C25···H29Axii2.7825
Fe1···H28Ai3.4818C26···H24vii2.9843
Fe1···H28Bi3.3131C26···H29Axii3.0814
O11···C18v3.313 (10)C26···H23vii2.9192
O12···C19vi3.169 (10)C27···H28Bi2.7983
O21···C28iv3.36 (3)C27···H23vii2.1310
O22···C24vii3.37 (3)C28···H22v2.7979
O22···C23vii2.78 (3)C28···H28Ai2.9538
O11···H19Bviii2.6901C28···H23vii2.6807
O11···H18Av2.5230C29···H22v2.9790
O12···H19Bvi2.7493C29···H23vii2.3326
O12···H152.3980H12···H18Bv2.4753
O12···H19Avi2.7879H12···C18v2.8674
O21···H28Aiv2.5819H15···O122.3980
O22···H252.4133H18A···N11i2.5619
O22···H23vii1.9117H18A···C17i2.9204
N21···C23vii3.41 (4)H18A···C18i2.8988
N11···H18Aix2.5619H18A···H18Ai2.5383
N21···H28Ai2.7335H18A···O11iv2.5230
N21···H23vii2.5732H18A···H18Aix2.5383
N21···H28Bi2.6365H18B···C17i2.8411
C15···C19x3.591 (12)H18B···C16i2.8769
C16···C18ix3.567 (14)H18B···C14x3.0003
C17···C18ix3.200 (14)H18B···C15x3.0100
C18···C16i3.567 (14)H18B···H12iv2.4753
C18···O11iv3.313 (11)H19A···O12vi2.7879
C18···C17i3.200 (16)H19A···C12x3.0623
C19···O12vi3.169 (10)H19A···C13x3.0756
C19···C19vi3.129 (13)H19A···C11x3.0573
C19···C15x3.591 (12)H19A···H19Bvi2.5383
C21···C22x3.39 (3)H19A···C19vi2.9227
C22···C21x3.39 (3)H19A···C16x2.9770
C22···C22x3.15 (3)H19A···C14x3.0439
C22···C28iv3.50 (4)H19A···C15x2.9842
C23···C29xi3.20 (3)H19B···C11ii2.9092
C23···N21xi3.41 (4)H19B···O12vi2.7493
C23···C28xi3.53 (3)H19B···C19vi2.8858
C23···O22xi2.78 (3)H19B···H19Avi2.5383
C23···C27xi2.98 (4)H19B···O11ii2.6901
C23···C26xi3.51 (5)H22···C28iv2.7979
C24···C29xii3.40 (3)H22···C29iv2.9790
C24···C26xi3.54 (5)H22···H28Biv2.4120
C24···O22xi3.37 (3)H22···C21x3.0734
C24···C25xi3.43 (5)H22···C22x3.0312
C24···C27xi3.53 (4)H23···O22xi1.9117
C25···C24vii3.43 (4)H23···N21xi2.5732
C25···C29xii3.36 (3)H23···C26xi2.9192
C26···C23vii3.51 (4)H23···C27xi2.1310
C26···C24vii3.54 (4)H23···C28xi2.6807
C27···C23vii2.98 (4)H23···C29xi2.3326
C27···C28i3.38 (3)H23···H29Axi2.2204
C27···C24vii3.53 (4)H24···C25xi2.5989
C28···C22v3.50 (4)H24···C26xi2.9843
C28···C27ix3.39 (4)H24···H25xi2.4548
C28···O21v3.36 (3)H25···O222.4133
C28···C28ix3.50 (4)H25···H24vii2.4548
C28···C23vii3.53 (3)H28A···Fe1viii3.4889
C28···C28i3.50 (3)H28A···Fe1v3.4889
C29···C23vii3.20 (3)H28A···O21v2.5819
C29···C25xiii3.36 (3)H28A···N21ix2.7337
C29···C24xiii3.40 (4)H28A···C28ix2.9541
C11···H19Ax3.0573H28A···H28Aix2.3817
C11···H19Bviii2.9092H28A···Fe1xiv3.4889
C12···H19Ax3.0623H28A···H28Ai2.3817
C13···H19Ax3.0756H28B···N21ix2.6360
C14···H19Ax3.0439H28B···C27ix2.7985
C14···H18Bx3.0003H28B···H22v2.4120
C15···H19Ax2.9842H29A···C23vii2.8845
C15···H18Bx3.0100H29A···C25xiii2.7825
C16···H19Ax2.9770H29A···C26xiii3.0814
C16···H18Bix2.8769H29A···H23vii2.2204
C17···H18Bix2.8411H29B···C24xiii2.7784
O11—Fe1—N1183.7 (3)C22—C23—C24121 (2)
O11—Fe1—O11ix98.8 (3)C23—C24—C25121 (3)
O11—Fe1—N11ix93.4 (3)C24—C25—C26118 (2)
O11—Fe1—O11i98.8 (3)C21—C26—C25120 (2)
O11—Fe1—N11i167.0 (3)C21—C26—C27122 (2)
O11ix—Fe1—N11167.0 (3)C25—C26—C27118 (2)
N11—Fe1—N11ix83.4 (3)O22—C27—N21114.8 (19)
O11i—Fe1—N1193.4 (3)O22—C27—C26118 (2)
N11—Fe1—N11i83.4 (3)N21—C27—C26127 (2)
O21—Fe1—N2185.6 (8)N21—C28—C29103.5 (18)
O21—Fe1—O21ix105.9 (9)O22—C29—C28106.0 (16)
O21—Fe1—N21ix162.3 (9)C11—C12—H12119.51
O21—Fe1—O21i105.9 (9)C13—C12—H12119.66
O21—Fe1—N21i83.0 (10)C12—C13—H13119.36
O21ix—Fe1—N2183.0 (9)C14—C13—H13119.27
N21—Fe1—N21ix82.5 (9)C13—C14—H14120.38
O21i—Fe1—N21162.3 (9)C15—C14—H14120.34
N21—Fe1—N21i82.5 (8)C14—C15—H15119.58
Fe1—O11—C11136.2 (5)C16—C15—H15119.53
C17—O12—C19107.8 (7)N11—C18—H18A110.83
Fe1—O21—C21135.2 (15)N11—C18—H18B110.84
C27—O22—C29107.0 (18)C19—C18—H18A110.81
C17—N11—C18107.1 (7)C19—C18—H18B110.87
Fe1—N11—C17127.3 (5)H18A—C18—H18B108.89
Fe1—N11—C18125.5 (6)O12—C19—H19A110.88
Fe1—N21—C27124.2 (15)O12—C19—H19B110.87
Fe1—N21—C28125.5 (17)C18—C19—H19A110.85
C27—N21—C28108.4 (19)C18—C19—H19B110.87
O11—C11—C12119.5 (8)H19A—C19—H19B108.93
O11—C11—C16122.6 (8)C21—C22—H22119.88
C12—C11—C16117.9 (9)C23—C22—H22119.98
C11—C12—C13120.8 (9)C22—C23—H23119.54
C12—C13—C14121.4 (9)C24—C23—H23119.65
C13—C14—C15119.3 (10)C23—C24—H24119.25
C14—C15—C16120.9 (8)C25—C24—H24119.36
C11—C16—C15119.7 (8)C24—C25—H25120.66
C15—C16—C17118.9 (7)C26—C25—H25120.91
C11—C16—C17121.5 (8)N21—C28—H28A111.08
O12—C17—N11115.5 (7)N21—C28—H28B110.86
N11—C17—C16126.7 (7)C29—C28—H28A111.26
O12—C17—C16117.8 (8)C29—C28—H28B111.00
N11—C18—C19104.6 (8)H28A—C28—H28B109.05
O12—C19—C18104.4 (6)O22—C29—H29A110.61
O21—C21—C22119 (2)O22—C29—H29B110.42
O21—C21—C26122 (2)C28—C29—H29A110.65
C22—C21—C26119 (2)C28—C29—H29B110.48
C21—C22—C23120 (2)H29A—C29—H29B108.65
N11—Fe1—O11—C1116.1 (8)C17—N11—C18—C196.5 (8)
O11ix—Fe1—O11—C11150.9 (8)Fe1—N11—C17—O12179.4 (5)
N11ix—Fe1—O11—C1166.8 (8)Fe1—N11—C17—C160.5 (11)
O11i—Fe1—O11—C11108.7 (8)O11—C11—C12—C13179.0 (8)
O11—Fe1—N11—C178.4 (7)O11—C11—C16—C15179.4 (8)
O11—Fe1—N11—C18169.4 (6)O11—C11—C16—C172.2 (12)
N11ix—Fe1—N11—C1785.9 (7)C16—C11—C12—C133.7 (13)
N11ix—Fe1—N11—C1896.4 (6)C12—C11—C16—C17175.1 (8)
O11i—Fe1—N11—C17106.8 (7)C12—C11—C16—C153.3 (12)
O11i—Fe1—N11—C1870.9 (6)C11—C12—C13—C142.2 (14)
N11i—Fe1—N11—C17169.9 (7)C12—C13—C14—C150.3 (14)
N11i—Fe1—N11—C1812.3 (6)C13—C14—C15—C160.0 (14)
Fe1—O11—C11—C12169.0 (6)C14—C15—C16—C111.6 (13)
Fe1—O11—C11—C1613.8 (13)C14—C15—C16—C17176.9 (8)
C19—O12—C17—N112.9 (9)C11—C16—C17—O12172.7 (7)
C19—O12—C17—C16176.1 (6)C15—C16—C17—N11173.2 (8)
C17—O12—C19—C186.7 (8)C11—C16—C17—N118.4 (12)
C18—N11—C17—O122.5 (9)C15—C16—C17—O125.7 (11)
C18—N11—C17—C16178.6 (7)N11—C18—C19—O127.9 (8)
Fe1—N11—C18—C19175.4 (5)
Symmetry codes: (i) x+y+1, x+1, z; (ii) x, y, z1; (iii) y+1, xy, z1; (iv) x+y+1, x+1, z1; (v) y+1, xy, z+1; (vi) x+1, y+1, z; (vii) y, x+y, z+1; (viii) x, y, z+1; (ix) y+1, xy, z; (x) x+1, y+1, z+1; (xi) xy, x, z+1; (xii) xy, x, z+2; (xiii) y, x+y, z+2; (xiv) x+y+1, x+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C15—H15···O120.952.402.736 (11)101
C18—H18A···O11iv0.992.523.313 (11)137
C18—H18A···N11i0.992.562.914 (14)101
C28—H28A···O21v0.992.583.36 (3)136
Symmetry codes: (i) x+y+1, x+1, z; (iv) x+y+1, x+1, z1; (v) y+1, xy, z+1.

Experimental details

Crystal data
Chemical formula[Fe(C9H8NO2)3]
Mr542.34
Crystal system, space groupTrigonal, P3
Temperature (K)150
a, c (Å)14.882 (2), 6.4052 (11)
V3)1228.5 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.66
Crystal size (mm)0.30 × 0.15 × 0.05
Data collection
DiffractometerEnraf-Nonius CAD-4 Turbo
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
1686, 1448, 970
Rint0.057
(sin θ/λ)max1)0.594
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.074, 0.168, 1.19
No. of reflections1448
No. of parameters161
No. of restraints31
H-atom treatmentH-atom parameters not refined
Δρmax, Δρmin (e Å3)0.51, 0.53

Computer programs: locally modified CAD-4 Software (Enraf-Nonius, 1989), SET4 (de Boer & Duisenberg, 1984), HELENA (Spek, 1997), SHELXS86 (Sheldrick, 1985), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2002), PLATON.

Selected geometric parameters (Å, º) top
Fe1—O111.940 (7)O22—C271.35 (3)
Fe1—N112.132 (7)O22—C291.44 (3)
Fe1—O211.870 (19)N11—C171.313 (13)
Fe1—N212.10 (2)N11—C181.476 (11)
O11—C111.338 (12)N21—C271.30 (3)
O12—C171.343 (10)N21—C281.47 (3)
O12—C191.448 (11)C18—C191.505 (14)
O21—C211.35 (3)C28—C291.49 (3)
O11—Fe1—N1183.7 (3)O21—Fe1—N2185.6 (8)
O11—Fe1—O11i98.8 (3)O21—Fe1—O21i105.9 (9)
O11—Fe1—N11i93.4 (3)O21—Fe1—N21i162.3 (9)
O11—Fe1—N11ii167.0 (3)O21—Fe1—N21ii83.0 (10)
N11—Fe1—N11i83.4 (3)N21—Fe1—N21i82.5 (9)
Symmetry codes: (i) y+1, xy, z; (ii) x+y+1, x+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C18—H18A···O11iii0.992.523.313 (11)137
C28—H28A···O21iv0.992.583.36 (3)136
Symmetry codes: (iii) x+y+1, x+1, z1; (iv) y+1, xy, z+1.
 

Follow Acta Cryst. C
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds