Bis[(E)-4-chloro-2-(2-furylmethyl­imino­meth­yl)phenolato]iron(II)

The Fe atom of the title compound, [Fe(C₁₂H₉ClNO₂)₂], lies on a crystallographic twofold rotation axis. The Fe^II atom is four-coordinated in a tetra­hedral geometry by the O and N atoms of the two Schiff base ligands. The O atom of the furan substituent in the ligand unit is not involved in coordination to the Fe atom.

Related literature

For related structures, see: Chen & Wang (2006); Chen et al. (2007); Ran et al. (2006); Ye et al. (2007); Zhu et al. (2003).

Experimental

Crystal data

• [Fe(C₁₂H₉ClNO₂)₂]

• M_r = 525.15

• Monoclinic, C 2

• a = 22.550 (4) Å

• b = 4.6270 (6) Å

• c = 13.822 (3) Å

• β = 127.73 (3)°

• V = 1140.6 (4) ų

• Z = 2

• Mo Kα radiation

• μ = 0.93 mm⁻¹

• T = 298 (2) K

• 0.21 × 0.21 × 0.20 mm

Data collection

• Bruker SMART CCD area-detector diffractometer

• Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.829, T_max = 0.836

• 1314 measured reflections

• 1262 independent reflections

• 973 reflections with I > 2σ(I)

• R_int = 0.035

Refinement

• R[F² > 2σ(F²)] = 0.060

• wR(F²) = 0.203

• S = 1.06

• 1262 reflections

• 151 parameters

• 1 restraint

• H-atom parameters constrained

• Δρ_max = 0.60 e Å⁻³

• Δρ_min = −0.40 e Å⁻³

• Absolute structure: Flack (1983), with no Friedel pairs

• Flack parameter: −0.02 (9)

Table 1
Selected geometric parameters (Å, °)

Fe1—O1	1.888 (8)
Fe1—N1	1.992 (8)

O1—Fe1—O1^i	124.0 (6)
O1—Fe1—N1	95.2 (3)
O1—Fe1—N1^i	113.5 (3)
N1—Fe1—N1^i	117.3 (5)
Symmetry code: (i) -x+1, y, -z+1.

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL .

Supporting information

S1. Comment

As part of our ongoing interest in the structure of iron complexes (Zhu et al., 2003), we report herein the crystal structure of the title compound, a new mononuclear iron(II) complex, (I), Fig. 1, derived from the Schiff base ligand 4-chloro-2-[(furan-2-ylmethylimino)methyl]phenol.

Compound (I) possesses crystallographic two-fold symmetry. The Fe^II atom in (I) is four-coordinate in a tetrahedral geometry, binding to the O and N atoms of two Schiff base ligands. The O atom of the furan substituent in the ligand lies well away from the coordination sphere of the Fe atom. The coordinate bond values (Table 1) are comparable to values observed in other iron(II) complexes (Chen & Wang, 2006; Chen et al., 2007; Ran et al., 2006; Ye et al., 2007).

Related literature

For related structures, see: Chen & Wang (2006); Chen et al. (2007); Ran et al. (2006); Ye et al. (2007); Zhu et al. (2003).

S2. Experimental

5-Chlorosalicylaldehyde (62.4 mg, 0.2 mmol), furan-2-ylmethylamine (19.4 mg, 0.2 mmol), and FeCl₂ (12.6 mg, 0.1 mmol) were dissolved in methanol (30 ml). The mixture was stirred for 30 min at room temperature. The resulting solution was kept still in air for a few days, yielding brown crystals.

S3. Refinement

H atoms were placed in idealized positions and constrained to ride on their parent atoms with C–H distances in the range 0.93–0.97 Å, and with U_iso(H) set at 1.2U_eq(C).

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures

Fig. 1. The structure of (I) showing 30% probability displacement ellipsoids and the atom-numbering scheme. Numbered atoms are related to un-numbered atoms by the symmetry code 1-x, y, 1-z.

Bis[(E)-4-chloro-2-(2-furylmethyliminomethyl)phenolato]iron(II)

Crystal data

[Fe(C12H9ClNO2)2]	F(000) = 536
Mr = 525.15	Dx = 1.529 Mg m^−3
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 823 reflections
a = 22.550 (4) Å	θ = 2.4–26.2°
b = 4.6270 (6) Å	µ = 0.93 mm^−1
c = 13.822 (3) Å	T = 298 K
β = 127.73 (3)°	Block, brown
V = 1140.6 (4) Å^3	0.21 × 0.21 × 0.20 mm
Z = 2

Data collection

Bruker SMART CCD area-detector diffractometer	1262 independent reflections
Radiation source: fine-focus sealed tube	973 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
ω scans	θmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −21→27
Tmin = 0.829, Tmax = 0.836	k = −5→0
1314 measured reflections	l = −17→0

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.060	w = 1/[σ^2(Fo^2) + (0.1149P)^2 + 2.2051P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.203	(Δ/σ)max = 0.001
S = 1.06	Δρmax = 0.60 e Å^−3
1262 reflections	Δρmin = −0.40 e Å^−3
151 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.011 (3)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 0 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.02 (9)

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 > 2sigma(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 (Ų)

	x	y	z	Uiso*/Ueq
Fe1	0.5000	0.5044 (3)	0.5000	0.0419 (6)
Cl1	0.87863 (17)	0.7649 (11)	1.0179 (3)	0.0929 (13)
N1	0.5246 (5)	0.728 (2)	0.6435 (8)	0.055 (2)
O1	0.5933 (4)	0.313 (2)	0.5865 (7)	0.067 (2)
O2	0.4619 (6)	0.600 (3)	0.7844 (9)	0.102 (4)
C1	0.6584 (5)	0.630 (3)	0.7611 (9)	0.053 (2)
C2	0.6554 (5)	0.419 (2)	0.6848 (9)	0.053 (3)
C3	0.7253 (6)	0.309 (3)	0.7192 (11)	0.069 (3)
H3	0.7250	0.1686	0.6709	0.083*
C4	0.7929 (6)	0.406 (3)	0.8218 (11)	0.068 (3)
H4	0.8377	0.3317	0.8429	0.081*
C5	0.7933 (6)	0.620 (3)	0.8943 (10)	0.065 (3)
C6	0.7284 (6)	0.737 (3)	0.8663 (10)	0.070 (3)
H6	0.7300	0.8824	0.9145	0.084*
C7	0.5937 (6)	0.759 (3)	0.7390 (10)	0.066 (3)
H7	0.6021	0.8786	0.8003	0.079*
C8	0.4677 (6)	0.890 (3)	0.6455 (11)	0.067 (3)
H8A	0.4926	1.0336	0.7100	0.080*
H8B	0.4329	0.9882	0.5681	0.080*
C9	0.4259 (6)	0.683 (3)	0.6671 (10)	0.061 (3)
C10	0.4146 (12)	0.427 (6)	0.786 (2)	0.137 (10)
H10	0.4242	0.3498	0.8560	0.164*
C11	0.3509 (10)	0.381 (4)	0.6710 (18)	0.105 (6)
H11	0.3109	0.2606	0.6466	0.126*
C12	0.3594 (7)	0.555 (4)	0.5982 (13)	0.087 (5)
H12	0.3238	0.5781	0.5141	0.104*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0384 (9)	0.0462 (11)	0.0399 (9)	0.000	0.0233 (7)	0.000
Cl1	0.0661 (17)	0.122 (3)	0.0664 (18)	−0.012 (2)	0.0279 (15)	0.017 (2)
N1	0.062 (5)	0.047 (5)	0.065 (5)	0.000 (5)	0.044 (4)	−0.005 (4)
O1	0.065 (4)	0.068 (6)	0.066 (4)	−0.001 (4)	0.040 (4)	−0.017 (4)
O2	0.093 (6)	0.136 (12)	0.089 (6)	0.016 (7)	0.062 (5)	0.022 (7)
C1	0.052 (5)	0.054 (6)	0.053 (5)	0.001 (5)	0.032 (5)	0.006 (5)
C2	0.053 (5)	0.050 (8)	0.053 (5)	0.005 (5)	0.031 (5)	0.009 (5)
C3	0.061 (6)	0.062 (8)	0.088 (8)	−0.007 (6)	0.048 (6)	−0.008 (7)
C4	0.056 (6)	0.070 (9)	0.081 (7)	0.012 (6)	0.043 (6)	0.019 (7)
C5	0.048 (6)	0.081 (9)	0.055 (6)	0.001 (6)	0.026 (5)	0.013 (6)
C6	0.071 (7)	0.077 (9)	0.059 (6)	−0.001 (7)	0.038 (6)	0.010 (7)
C7	0.074 (7)	0.067 (8)	0.054 (6)	−0.004 (7)	0.038 (6)	0.002 (6)
C8	0.070 (7)	0.059 (7)	0.079 (7)	0.019 (6)	0.049 (6)	0.009 (6)
C9	0.061 (6)	0.067 (8)	0.070 (7)	0.011 (6)	0.048 (6)	0.005 (6)
C10	0.161 (17)	0.15 (3)	0.199 (19)	0.037 (18)	0.158 (17)	0.06 (2)
C11	0.112 (12)	0.085 (11)	0.167 (17)	0.000 (11)	0.110 (13)	−0.004 (13)
C12	0.080 (8)	0.088 (14)	0.102 (9)	−0.001 (9)	0.061 (8)	−0.007 (9)

Geometric parameters (Å, º)

Fe1—O1	1.888 (8)	C3—H3	0.9300
Fe1—O1^i	1.888 (8)	C4—C5	1.402 (17)
Fe1—N1	1.992 (8)	C4—H4	0.9300
Fe1—N1^i	1.992 (8)	C5—C6	1.377 (16)
Cl1—C5	1.746 (12)	C6—H6	0.9300
N1—C7	1.294 (13)	C7—H7	0.9300
N1—C8	1.499 (12)	C8—C9	1.493 (16)
O1—C2	1.310 (12)	C8—H8A	0.9700
O2—C10	1.34 (2)	C8—H8B	0.9700
O2—C9	1.352 (14)	C9—C12	1.328 (18)
C1—C2	1.411 (14)	C10—C11	1.35 (2)
C1—C7	1.424 (15)	C10—H10	0.9300
C1—C6	1.429 (15)	C11—C12	1.39 (2)
C2—C3	1.431 (15)	C11—H11	0.9300
C3—C4	1.374 (16)	C12—H12	0.9300
O1—Fe1—O1^i	124.0 (6)	C4—C5—Cl1	119.4 (9)
O1—Fe1—N1	95.2 (3)	C5—C6—C1	118.1 (13)
O1^i—Fe1—N1	113.5 (3)	C5—C6—H6	121.0
O1—Fe1—N1^i	113.5 (3)	C1—C6—H6	121.0
O1^i—Fe1—N1^i	95.2 (3)	N1—C7—C1	127.6 (11)
N1—Fe1—N1^i	117.3 (5)	N1—C7—H7	116.2
C7—N1—C8	115.9 (9)	C1—C7—H7	116.2
C7—N1—Fe1	120.0 (8)	C9—C8—N1	109.7 (10)
C8—N1—Fe1	123.9 (7)	C9—C8—H8A	109.7
C2—O1—Fe1	123.4 (7)	N1—C8—H8A	109.7
C10—O2—C9	106.7 (14)	C9—C8—H8B	109.7
C2—C1—C7	123.7 (10)	N1—C8—H8B	109.7
C2—C1—C6	121.3 (10)	H8A—C8—H8B	108.2
C7—C1—C6	115.0 (11)	C12—C9—O2	108.5 (12)
O1—C2—C1	124.5 (9)	C12—C9—C8	135.8 (12)
O1—C2—C3	118.3 (10)	O2—C9—C8	115.7 (11)
C1—C2—C3	117.3 (9)	O2—C10—C11	111.3 (16)
C4—C3—C2	121.8 (12)	O2—C10—H10	124.4
C4—C3—H3	119.1	C11—C10—H10	124.4
C2—C3—H3	119.1	C10—C11—C12	103.7 (16)
C3—C4—C5	119.1 (10)	C10—C11—H11	128.2
C3—C4—H4	120.5	C12—C11—H11	128.2
C5—C4—H4	120.5	C9—C12—C11	109.7 (14)
C6—C5—C4	122.4 (11)	C9—C12—H12	125.2
C6—C5—Cl1	117.9 (11)	C11—C12—H12	125.2

Symmetry code: (i) −x+1, y, −z+1.