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In the title mononuclear iron(II) complex, [Fe(C13H14ClNO)2], the FeII cation lies on a twofold rotation axis. It is four-coordinated in a tetra­hedral geometry by the imino N and phenolate O atoms of the two chelating Schiff base ligands.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806017247/sj2064sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806017247/sj2064Isup2.hkl
Contains datablock I

CCDC reference: 610901

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C)= 0.005 Å
  • R factor = 0.052
  • wR factor = 0.108
  • Data-to-parameter ratio = 15.4

checkCIF/PLATON results

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Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Bis{2-[(4-chlorophenylimino)methyl]phenolato}iron(II) top
Crystal data top
[Fe(C13H9ClNO)2]F(000) = 1056
Mr = 517.17Dx = 1.529 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 953 reflections
a = 21.870 (5) Åθ = 2.5–25.2°
b = 8.762 (2) ŵ = 0.94 mm1
c = 11.788 (3) ÅT = 298 K
β = 95.964 (3)°Needle, brown
V = 2246.8 (9) Å30.18 × 0.09 × 0.09 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
2313 independent reflections
Radiation source: fine-focus sealed tube1589 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.058
ω scansθmax = 26.5°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2726
Tmin = 0.850, Tmax = 0.921k = 1010
8075 measured reflectionsl = 1414
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)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0392P)2 + 0.3814P]
where P = (Fo2 + 2Fc2)/3
2313 reflections(Δ/σ)max < 0.001
150 parametersΔρmax = 0.38 e Å3
0 restraintsΔρmin = 0.26 e Å3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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) top
xyzUiso*/Ueq
Fe10.00000.01709 (7)0.75000.0408 (2)
Cl10.15534 (5)0.56807 (11)0.39168 (9)0.0766 (4)
O10.07521 (9)0.0872 (3)0.78785 (18)0.0535 (6)
N10.02530 (11)0.1303 (3)0.6155 (2)0.0402 (6)
C10.12393 (14)0.0042 (4)0.6253 (3)0.0449 (8)
C20.12186 (14)0.0897 (4)0.7262 (3)0.0438 (8)
C30.17180 (15)0.1847 (4)0.7610 (3)0.0536 (9)
H30.17120.24170.82750.064*
C40.22144 (16)0.1959 (5)0.6998 (3)0.0637 (11)
H40.25400.25980.72520.076*
C50.22357 (17)0.1133 (5)0.6011 (4)0.0717 (12)
H50.25740.12190.55980.086*
C60.17623 (15)0.0187 (4)0.5637 (3)0.0613 (10)
H60.17810.03710.49700.074*
C70.07757 (14)0.0979 (4)0.5764 (3)0.0460 (8)
H70.08540.14680.50950.055*
C80.01572 (13)0.2392 (4)0.5574 (3)0.0412 (8)
C90.01230 (15)0.2894 (4)0.4467 (3)0.0470 (8)
H90.01900.25390.40600.056*
C100.05462 (17)0.3907 (4)0.3965 (3)0.0538 (9)
H100.05220.42340.32210.065*
C110.10065 (16)0.4436 (4)0.4573 (3)0.0515 (9)
C120.10401 (15)0.4003 (4)0.5679 (3)0.0568 (9)
H120.13440.43970.60910.068*
C130.06166 (14)0.2975 (4)0.6174 (3)0.0510 (9)
H130.06390.26680.69240.061*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0367 (4)0.0524 (4)0.0348 (4)0.0000.0112 (3)0.000
Cl10.0751 (7)0.0658 (7)0.0841 (8)0.0062 (5)0.0142 (6)0.0165 (5)
O10.0432 (13)0.0749 (16)0.0449 (14)0.0088 (12)0.0164 (11)0.0038 (12)
N10.0351 (15)0.0537 (17)0.0324 (14)0.0057 (12)0.0058 (12)0.0046 (12)
C10.0331 (17)0.061 (2)0.0416 (19)0.0063 (16)0.0060 (14)0.0106 (17)
C20.0388 (19)0.055 (2)0.0377 (19)0.0025 (16)0.0041 (16)0.0116 (16)
C30.044 (2)0.063 (2)0.053 (2)0.0037 (17)0.0013 (17)0.0089 (18)
C40.039 (2)0.078 (3)0.072 (3)0.0048 (19)0.001 (2)0.022 (2)
C50.040 (2)0.100 (3)0.077 (3)0.008 (2)0.019 (2)0.024 (3)
C60.044 (2)0.081 (3)0.061 (2)0.010 (2)0.0144 (18)0.006 (2)
C70.044 (2)0.058 (2)0.0359 (18)0.0117 (17)0.0068 (16)0.0037 (16)
C80.0365 (18)0.0489 (19)0.0383 (18)0.0103 (15)0.0039 (15)0.0018 (15)
C90.054 (2)0.055 (2)0.0324 (18)0.0087 (17)0.0043 (16)0.0034 (16)
C100.068 (2)0.056 (2)0.0364 (19)0.012 (2)0.0009 (18)0.0018 (17)
C110.052 (2)0.047 (2)0.053 (2)0.0088 (16)0.0058 (18)0.0044 (17)
C120.041 (2)0.071 (2)0.059 (2)0.0002 (18)0.0120 (18)0.008 (2)
C130.0409 (19)0.070 (2)0.043 (2)0.0012 (17)0.0043 (16)0.0117 (18)
Geometric parameters (Å, º) top
Fe1—O1i1.894 (2)C4—H40.9300
Fe1—O11.894 (2)C5—C61.364 (5)
Fe1—N1i1.996 (3)C5—H50.9300
Fe1—N11.996 (3)C6—H60.9300
Cl1—C111.740 (3)C7—H70.9300
O1—C21.313 (3)C8—C131.385 (4)
N1—C71.307 (4)C8—C91.386 (4)
N1—C81.434 (4)C9—C101.372 (4)
C1—C21.411 (4)C9—H90.9300
C1—C61.423 (4)C10—C111.375 (5)
C1—C71.428 (4)C10—H100.9300
C2—C31.400 (4)C11—C121.367 (5)
C3—C41.368 (5)C12—C131.378 (4)
C3—H30.9300C12—H120.9300
C4—C51.375 (5)C13—H130.9300
O1i—Fe1—O1122.30 (14)C5—C6—C1120.8 (4)
O1i—Fe1—N1i96.97 (10)C5—C6—H6119.6
O1—Fe1—N1i111.00 (9)C1—C6—H6119.6
O1i—Fe1—N1111.00 (9)N1—C7—C1127.2 (3)
O1—Fe1—N196.97 (10)N1—C7—H7116.4
N1i—Fe1—N1120.39 (15)C1—C7—H7116.4
C2—O1—Fe1125.7 (2)C13—C8—C9118.5 (3)
C7—N1—C8120.2 (3)C13—C8—N1116.9 (3)
C7—N1—Fe1119.8 (2)C9—C8—N1124.7 (3)
C8—N1—Fe1119.93 (19)C10—C9—C8120.8 (3)
C2—C1—C6118.8 (3)C10—C9—H9119.6
C2—C1—C7126.1 (3)C8—C9—H9119.6
C6—C1—C7115.1 (3)C9—C10—C11119.4 (3)
O1—C2—C3118.4 (3)C9—C10—H10120.3
O1—C2—C1123.6 (3)C11—C10—H10120.3
C3—C2—C1118.1 (3)C12—C11—C10121.2 (3)
C4—C3—C2121.7 (4)C12—C11—Cl1119.7 (3)
C4—C3—H3119.1C10—C11—Cl1119.1 (3)
C2—C3—H3119.1C11—C12—C13119.0 (3)
C3—C4—C5120.5 (4)C11—C12—H12120.5
C3—C4—H4119.8C13—C12—H12120.5
C5—C4—H4119.8C12—C13—C8121.1 (3)
C6—C5—C4120.2 (4)C12—C13—H13119.5
C6—C5—H5119.9C8—C13—H13119.5
C4—C5—H5119.9
Symmetry code: (i) x, y, z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9···O1ii0.932.443.324 (3)160
C13—H13···N1i0.932.623.488 (3)155
Symmetry codes: (i) x, y, z+3/2; (ii) x, y, z1/2.
 

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