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The title compound, [FeCl(C14H11NO2)]2, represents the first structurally characterized complex of the N-(2-oxy­methyl­phenyl)­salicyl­idene­iminate tridentate ligand. The mol­ecule of the binuclear iron complex occupies a special position on a crystallographic inversion centre. The Fe atoms are bridged by two O atoms originating from the alcohol, rather than the phenolic hydroxyl groups, with an Fe...Fe separation of 3.1282 (7) Å. The coordination polyhedron of the Fe atoms can be described as square pyramidal, with an O3N basal plane and an apical Cl atom or, alternatively, as trigonal bipyramidal, with the N atom and one of the bridging O atoms in the axial positions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804001709/ya6192sup1.cif
Contains datablocks General, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804001709/ya6192Isup2.hkl
Contains datablock I

CCDC reference: 234830

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.040
  • wR factor = 0.123
  • Data-to-parameter ratio = 16.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
Alert level G FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the _chemical_formula_sum and _chemical_formula_moiety. This is usually due to the moiety formula being in the wrong format. Atom count from _chemical_formula_sum: C28 H22 Cl2 Fe2 N2 O4 Atom count from _chemical_formula_moiety:
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: MSC/AFC Diffractometer Control (Molecular Structure Corporation, 1991); cell refinement: MSC/AFC Diffractometer Control; data reduction: CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2003); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Watkin et al., 1996); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.

(I) top
Crystal data top
[Fe2(C28H22N2O4)Cl2]F(000) = 644.00
Mr = 633.09Dx = 1.568 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ynCell parameters from 25 reflections
a = 10.182 (2) Åθ = 10.1–12.4°
b = 12.131 (2) ŵ = 1.32 mm1
c = 11.300 (2) ÅT = 296 K
β = 106.11 (1)°Prism, dark brown
V = 1340.9 (4) Å30.30 × 0.20 × 0.20 mm
Z = 2
Data collection top
Rigaku AFC5S
diffractometer
Rint = 0.041
ω–2θ scansθmax = 27.5°
Absorption correction: ψ scan
(North et al., 1968)
h = 013
Tmin = 0.724, Tmax = 0.768k = 015
3405 measured reflectionsl = 1414
3081 independent reflections3 standard reflections every 150 reflections
1809 reflections with I > 2σ(I) intensity decay: 1.2%
Refinement top
Refinement on F2H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.040 w = (1/[σ(Fo2) + 0.0006Fo2])/(4Fo2)
wR(F2) = 0.123(Δ/σ)max < 0.001
S = 1.00Δρmax = 1.02 e Å3
3079 reflectionsΔρmin = 1.65 e Å3
183 parameters
Special details top

Geometry. ————– Plane number 1 —————

Atoms Defining Plane Distance e.s.d. O1 [1;0;0;0] 0.2073 0.0014 O2 [1;0;0;0] 0.2246 0.0015 N1 [1;0;0;0] -0.2150 0.0014 O1 [2;1;0;1] -0.2007 0.0013

Additional Atoms Distance e.s.d. Fe1 (1) -0.5473 0.0015

Mean deviation from plane is 0.2119 angstrom Chi-squared: 22704.244

————– Plane number 2 —————

Atoms Defining Plane Distance e.s.d. O1 [1;0;0;0] -0.0277 0.0016 O2 [1;0;0;0] -0.0364 0.0021 Cl1 [1;0;0;0] -0.0041 0.0002 Fe1 [1;0;0;0] 0.0028 0.0002

Additional Atoms Distance e.s.d. Fe1 (1) 0.0028 0.0007

Mean deviation from plane is 0.0177 angstrom Chi-squared: 470.910

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Fe10.61814 (5)0.08380 (4)0.55417 (4)0.0323 (1)
Cl10.5506 (1)0.24033 (9)0.6207 (1)0.0565 (3)
O10.5356 (3)0.0526 (2)0.5934 (2)0.0400 (7)
O20.7415 (3)0.1125 (3)0.4634 (2)0.0473 (8)
N10.7818 (3)0.0481 (2)0.7076 (3)0.0316 (7)
C10.5874 (4)0.1264 (3)0.6939 (3)0.041 (1)
C20.6494 (4)0.0640 (3)0.8113 (3)0.0362 (9)
C30.6136 (4)0.0896 (4)0.9181 (3)0.045 (1)
C40.6745 (5)0.0384 (4)1.0280 (4)0.054 (1)
C50.7722 (5)0.0409 (4)1.0341 (4)0.051 (1)
C60.8099 (4)0.0692 (3)0.9291 (3)0.044 (1)
C70.7500 (4)0.0165 (3)0.8185 (3)0.0338 (9)
C80.9091 (4)0.0673 (3)0.7120 (4)0.039 (1)
C90.9594 (4)0.1078 (3)0.6153 (4)0.040 (1)
C101.1003 (4)0.1287 (4)0.6401 (5)0.057 (1)
C111.1561 (5)0.1701 (4)0.5539 (5)0.065 (2)
C121.0731 (5)0.1924 (4)0.4372 (5)0.055 (1)
C130.9348 (4)0.1731 (4)0.4070 (4)0.050 (1)
C140.8749 (4)0.1310 (3)0.4952 (4)0.042 (1)
H10.51480.17100.70440.047*
H20.65540.17200.67620.047*
H30.54540.14380.91500.053*
H40.64900.05801.10000.065*
H50.81400.07651.11010.057*
H60.87680.12480.93310.049*
H70.97510.05250.78820.044*
H81.15820.11330.72010.066*
H91.25160.18360.57340.081*
H101.11230.22160.37680.072*
H110.87970.18820.32590.063*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0268 (2)0.0341 (3)0.0318 (3)0.0050 (2)0.0012 (2)0.0005 (3)
Cl10.0540 (6)0.0481 (6)0.0592 (7)0.0133 (5)0.0024 (5)0.0072 (5)
O10.037 (1)0.041 (1)0.033 (1)0.013 (1)0.005 (1)0.005 (1)
O20.035 (1)0.068 (2)0.038 (1)0.007 (1)0.009 (1)0.000 (1)
N10.027 (1)0.032 (2)0.032 (1)0.003 (1)0.002 (1)0.003 (1)
C10.045 (2)0.036 (2)0.036 (2)0.007 (2)0.001 (2)0.009 (2)
C20.034 (2)0.037 (2)0.033 (2)0.004 (2)0.001 (1)0.006 (1)
C30.039 (2)0.050 (2)0.044 (2)0.003 (2)0.009 (2)0.014 (2)
C40.062 (3)0.066 (3)0.035 (2)0.008 (2)0.014 (2)0.007 (2)
C50.064 (3)0.047 (2)0.032 (2)0.005 (2)0.001 (2)0.006 (2)
C60.047 (2)0.037 (2)0.039 (2)0.000 (2)0.005 (2)0.001 (2)
C70.032 (2)0.032 (2)0.033 (2)0.004 (1)0.000 (1)0.003 (1)
C80.029 (2)0.037 (2)0.045 (2)0.001 (2)0.000 (2)0.006 (2)
C90.030 (2)0.037 (2)0.053 (2)0.002 (2)0.011 (2)0.001 (2)
C100.033 (2)0.058 (3)0.073 (3)0.002 (2)0.006 (2)0.011 (2)
C110.035 (2)0.062 (3)0.105 (4)0.007 (2)0.033 (3)0.007 (3)
C120.056 (3)0.055 (3)0.068 (3)0.010 (2)0.039 (2)0.004 (2)
C130.056 (3)0.056 (3)0.047 (2)0.010 (2)0.025 (2)0.009 (2)
C140.039 (2)0.041 (2)0.048 (2)0.004 (2)0.017 (2)0.011 (2)
Geometric parameters (Å, º) top
Fe1—Cl12.220 (1)C9—C141.419 (5)
Fe1—O11.962 (3)C10—C111.354 (8)
Fe1—O1i1.981 (2)C11—C121.381 (7)
Fe1—O21.862 (3)C12—C131.374 (6)
Fe1—N12.090 (2)C13—C141.402 (7)
O1—C11.428 (4)Fe1—Fe1i3.1282 (7)
O2—C141.324 (5)C1—H10.950
N1—C71.431 (5)C1—H20.950
N1—C81.303 (5)C3—H30.950
C1—C21.506 (5)C4—H40.950
C2—C31.388 (6)C5—H50.950
C2—C71.401 (5)C6—H60.950
C3—C41.373 (6)C8—H70.950
C4—C51.372 (7)C10—H80.950
C5—C61.387 (6)C11—H90.950
C6—C71.386 (5)C12—H100.950
C8—C91.418 (6)C13—H110.950
C9—C101.406 (6)
Cl1—Fe1—O1116.90 (9)C14—C9—C8123.6 (3)
Cl1—Fe1—O2110.3 (1)C11—C10—C9122.1 (4)
Cl1—Fe1—N198.46 (9)C12—C11—C10119.5 (4)
Cl1—Fe1—O1i101.64 (3)C13—C12—C11121.2 (5)
O1—Fe1—O2132.8 (1)C14—C13—C12120.3 (4)
O1—Fe1—N186.0 (1)O2—C14—C9122.0 (4)
O1—Fe1—O1i74.99 (7)O2—C14—C13119.0 (3)
O2—Fe1—N189.5 (1)C9—C14—C13118.9 (4)
O2—Fe1—O1i93.90 (8)C2—C1—H1109.1
N1—Fe1—O1i157.00 (8)C2—C1—H2109.1
C1—O1—Fe1128.5 (2)H1—C1—H2109.5
C1—O1—Fe1i125.5 (2)H1—C1—O1109.1
Fe1—O1—Fe1i105.0 (1)H2—C1—O1109.1
C14—O2—Fe1132.8 (3)C4—C3—H3119.2
C7—N1—C8118.6 (3)H3—C3—C2119.2
C7—N1—Fe1117.3 (2)C5—C4—H4120.0
C8—N1—Fe1123.4 (3)H4—C4—C3119.9
C2—C1—O1110.9 (3)C6—C5—H5120.0
C3—C2—C7118.0 (3)H5—C5—C4120.0
C3—C2—C1120.4 (3)C7—C6—H6120.0
C7—C2—C1121.5 (4)H6—C6—C5120.0
C4—C3—C2121.6 (4)C9—C8—H7116.6
C5—C4—C3120.1 (4)H7—C8—N1116.6
C6—C5—C4120.0 (4)C11—C10—H8118.9
C7—C6—C5120.0 (4)H8—C10—C9118.9
N1—C7—C2118.4 (3)C12—C11—H9120.3
N1—C7—C6121.1 (3)H9—C11—C10120.3
C2—C7—C6120.4 (4)C13—C12—H10119.4
C9—C8—N1126.9 (3)H10—C12—C11119.4
C10—C9—C14118.0 (4)C14—C13—H11119.9
C10—C9—C8118.4 (4)H11—C13—C12119.9
Symmetry code: (i) x+1, y, z+1.
 

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