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The title compound, [FeCl(C
14H
11NO
2)]
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 O
3N 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
CCDC reference: 234830
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (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
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.
Crystal data top
[Fe2(C28H22N2O4)Cl2] | F(000) = 644.00 |
Mr = 633.09 | Dx = 1.568 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.7107 Å |
Hall symbol: -P 2yn | Cell parameters from 25 reflections |
a = 10.182 (2) Å | θ = 10.1–12.4° |
b = 12.131 (2) Å | µ = 1.32 mm−1 |
c = 11.300 (2) Å | T = 296 K |
β = 106.11 (1)° | Prism, dark brown |
V = 1340.9 (4) Å3 | 0.30 × 0.20 × 0.20 mm |
Z = 2 | |
Data collection top
Rigaku AFC5S diffractometer | Rint = 0.041 |
ω–2θ scans | θmax = 27.5° |
Absorption correction: ψ scan (North et al., 1968) | h = 0→13 |
Tmin = 0.724, Tmax = 0.768 | k = 0→15 |
3405 measured reflections | l = −14→14 |
3081 independent reflections | 3 standard reflections every 150 reflections |
1809 reflections with I > 2σ(I) | intensity decay: 1.2% |
Refinement top
Refinement on F2 | H-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 = 1.00 | Δρmax = 1.02 e Å−3 |
3079 reflections | Δρmin = −1.65 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
Fe1 | 0.61814 (5) | 0.08380 (4) | 0.55417 (4) | 0.0323 (1) | |
Cl1 | 0.5506 (1) | 0.24033 (9) | 0.6207 (1) | 0.0565 (3) | |
O1 | 0.5356 (3) | −0.0526 (2) | 0.5934 (2) | 0.0400 (7) | |
O2 | 0.7415 (3) | 0.1125 (3) | 0.4634 (2) | 0.0473 (8) | |
N1 | 0.7818 (3) | 0.0481 (2) | 0.7076 (3) | 0.0316 (7) | |
C1 | 0.5874 (4) | −0.1264 (3) | 0.6939 (3) | 0.041 (1) | |
C2 | 0.6494 (4) | −0.0640 (3) | 0.8113 (3) | 0.0362 (9) | |
C3 | 0.6136 (4) | −0.0896 (4) | 0.9181 (3) | 0.045 (1) | |
C4 | 0.6745 (5) | −0.0384 (4) | 1.0280 (4) | 0.054 (1) | |
C5 | 0.7722 (5) | 0.0409 (4) | 1.0341 (4) | 0.051 (1) | |
C6 | 0.8099 (4) | 0.0692 (3) | 0.9291 (3) | 0.044 (1) | |
C7 | 0.7500 (4) | 0.0165 (3) | 0.8185 (3) | 0.0338 (9) | |
C8 | 0.9091 (4) | 0.0673 (3) | 0.7120 (4) | 0.039 (1) | |
C9 | 0.9594 (4) | 0.1078 (3) | 0.6153 (4) | 0.040 (1) | |
C10 | 1.1003 (4) | 0.1287 (4) | 0.6401 (5) | 0.057 (1) | |
C11 | 1.1561 (5) | 0.1701 (4) | 0.5539 (5) | 0.065 (2) | |
C12 | 1.0731 (5) | 0.1924 (4) | 0.4372 (5) | 0.055 (1) | |
C13 | 0.9348 (4) | 0.1731 (4) | 0.4070 (4) | 0.050 (1) | |
C14 | 0.8749 (4) | 0.1310 (3) | 0.4952 (4) | 0.042 (1) | |
H1 | 0.5148 | −0.1710 | 0.7044 | 0.047* | |
H2 | 0.6554 | −0.1720 | 0.6762 | 0.047* | |
H3 | 0.5454 | −0.1438 | 0.9150 | 0.053* | |
H4 | 0.6490 | −0.0580 | 1.1000 | 0.065* | |
H5 | 0.8140 | 0.0765 | 1.1101 | 0.057* | |
H6 | 0.8768 | 0.1248 | 0.9331 | 0.049* | |
H7 | 0.9751 | 0.0525 | 0.7882 | 0.044* | |
H8 | 1.1582 | 0.1133 | 0.7201 | 0.066* | |
H9 | 1.2516 | 0.1836 | 0.5734 | 0.081* | |
H10 | 1.1123 | 0.2216 | 0.3768 | 0.072* | |
H11 | 0.8797 | 0.1882 | 0.3259 | 0.063* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Fe1 | 0.0268 (2) | 0.0341 (3) | 0.0318 (3) | −0.0050 (2) | 0.0012 (2) | 0.0005 (3) |
Cl1 | 0.0540 (6) | 0.0481 (6) | 0.0592 (7) | 0.0133 (5) | 0.0024 (5) | −0.0072 (5) |
O1 | 0.037 (1) | 0.041 (1) | 0.033 (1) | −0.013 (1) | −0.005 (1) | 0.005 (1) |
O2 | 0.035 (1) | 0.068 (2) | 0.038 (1) | −0.007 (1) | 0.009 (1) | 0.000 (1) |
N1 | 0.027 (1) | 0.032 (2) | 0.032 (1) | −0.003 (1) | 0.002 (1) | 0.003 (1) |
C1 | 0.045 (2) | 0.036 (2) | 0.036 (2) | −0.007 (2) | 0.001 (2) | 0.009 (2) |
C2 | 0.034 (2) | 0.037 (2) | 0.033 (2) | 0.004 (2) | 0.001 (1) | 0.006 (1) |
C3 | 0.039 (2) | 0.050 (2) | 0.044 (2) | −0.003 (2) | 0.009 (2) | 0.014 (2) |
C4 | 0.062 (3) | 0.066 (3) | 0.035 (2) | 0.008 (2) | 0.014 (2) | 0.007 (2) |
C5 | 0.064 (3) | 0.047 (2) | 0.032 (2) | 0.005 (2) | −0.001 (2) | −0.006 (2) |
C6 | 0.047 (2) | 0.037 (2) | 0.039 (2) | 0.000 (2) | −0.005 (2) | −0.001 (2) |
C7 | 0.032 (2) | 0.032 (2) | 0.033 (2) | 0.004 (1) | 0.000 (1) | 0.003 (1) |
C8 | 0.029 (2) | 0.037 (2) | 0.045 (2) | 0.001 (2) | −0.000 (2) | 0.006 (2) |
C9 | 0.030 (2) | 0.037 (2) | 0.053 (2) | −0.002 (2) | 0.011 (2) | 0.001 (2) |
C10 | 0.033 (2) | 0.058 (3) | 0.073 (3) | −0.002 (2) | 0.006 (2) | 0.011 (2) |
C11 | 0.035 (2) | 0.062 (3) | 0.105 (4) | −0.007 (2) | 0.033 (3) | 0.007 (3) |
C12 | 0.056 (3) | 0.055 (3) | 0.068 (3) | −0.010 (2) | 0.039 (2) | −0.004 (2) |
C13 | 0.056 (3) | 0.056 (3) | 0.047 (2) | −0.010 (2) | 0.025 (2) | −0.009 (2) |
C14 | 0.039 (2) | 0.041 (2) | 0.048 (2) | −0.004 (2) | 0.017 (2) | −0.011 (2) |
Geometric parameters (Å, º) top
Fe1—Cl1 | 2.220 (1) | C9—C14 | 1.419 (5) |
Fe1—O1 | 1.962 (3) | C10—C11 | 1.354 (8) |
Fe1—O1i | 1.981 (2) | C11—C12 | 1.381 (7) |
Fe1—O2 | 1.862 (3) | C12—C13 | 1.374 (6) |
Fe1—N1 | 2.090 (2) | C13—C14 | 1.402 (7) |
O1—C1 | 1.428 (4) | Fe1—Fe1i | 3.1282 (7) |
O2—C14 | 1.324 (5) | C1—H1 | 0.950 |
N1—C7 | 1.431 (5) | C1—H2 | 0.950 |
N1—C8 | 1.303 (5) | C3—H3 | 0.950 |
C1—C2 | 1.506 (5) | C4—H4 | 0.950 |
C2—C3 | 1.388 (6) | C5—H5 | 0.950 |
C2—C7 | 1.401 (5) | C6—H6 | 0.950 |
C3—C4 | 1.373 (6) | C8—H7 | 0.950 |
C4—C5 | 1.372 (7) | C10—H8 | 0.950 |
C5—C6 | 1.387 (6) | C11—H9 | 0.950 |
C6—C7 | 1.386 (5) | C12—H10 | 0.950 |
C8—C9 | 1.418 (6) | C13—H11 | 0.950 |
C9—C10 | 1.406 (6) | | |
| | | |
Cl1—Fe1—O1 | 116.90 (9) | C14—C9—C8 | 123.6 (3) |
Cl1—Fe1—O2 | 110.3 (1) | C11—C10—C9 | 122.1 (4) |
Cl1—Fe1—N1 | 98.46 (9) | C12—C11—C10 | 119.5 (4) |
Cl1—Fe1—O1i | 101.64 (3) | C13—C12—C11 | 121.2 (5) |
O1—Fe1—O2 | 132.8 (1) | C14—C13—C12 | 120.3 (4) |
O1—Fe1—N1 | 86.0 (1) | O2—C14—C9 | 122.0 (4) |
O1—Fe1—O1i | 74.99 (7) | O2—C14—C13 | 119.0 (3) |
O2—Fe1—N1 | 89.5 (1) | C9—C14—C13 | 118.9 (4) |
O2—Fe1—O1i | 93.90 (8) | C2—C1—H1 | 109.1 |
N1—Fe1—O1i | 157.00 (8) | C2—C1—H2 | 109.1 |
C1—O1—Fe1 | 128.5 (2) | H1—C1—H2 | 109.5 |
C1—O1—Fe1i | 125.5 (2) | H1—C1—O1 | 109.1 |
Fe1—O1—Fe1i | 105.0 (1) | H2—C1—O1 | 109.1 |
C14—O2—Fe1 | 132.8 (3) | C4—C3—H3 | 119.2 |
C7—N1—C8 | 118.6 (3) | H3—C3—C2 | 119.2 |
C7—N1—Fe1 | 117.3 (2) | C5—C4—H4 | 120.0 |
C8—N1—Fe1 | 123.4 (3) | H4—C4—C3 | 119.9 |
C2—C1—O1 | 110.9 (3) | C6—C5—H5 | 120.0 |
C3—C2—C7 | 118.0 (3) | H5—C5—C4 | 120.0 |
C3—C2—C1 | 120.4 (3) | C7—C6—H6 | 120.0 |
C7—C2—C1 | 121.5 (4) | H6—C6—C5 | 120.0 |
C4—C3—C2 | 121.6 (4) | C9—C8—H7 | 116.6 |
C5—C4—C3 | 120.1 (4) | H7—C8—N1 | 116.6 |
C6—C5—C4 | 120.0 (4) | C11—C10—H8 | 118.9 |
C7—C6—C5 | 120.0 (4) | H8—C10—C9 | 118.9 |
N1—C7—C2 | 118.4 (3) | C12—C11—H9 | 120.3 |
N1—C7—C6 | 121.1 (3) | H9—C11—C10 | 120.3 |
C2—C7—C6 | 120.4 (4) | C13—C12—H10 | 119.4 |
C9—C8—N1 | 126.9 (3) | H10—C12—C11 | 119.4 |
C10—C9—C14 | 118.0 (4) | C14—C13—H11 | 119.9 |
C10—C9—C8 | 118.4 (4) | H11—C13—C12 | 119.9 |
Symmetry code: (i) −x+1, −y, −z+1. |
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