Bis(2-benzyl­imino­methyl-4,6-dihydro­seleno­phenolato)iron(II)

Li, H.-Y.; Wang, L.-J.; Hou, J.; Zeng, Q.-F.

doi:10.1107/S1600536809032413

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page m1112

doi:10.1107/S1600536809032413

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Bis(2-benzyliminomethyl-4,6-dihydroselenophenolato)iron(II)

Hai-Yan Li,^a Li-Jun Wang,^a Jian Hou ^a and Qing-Fu Zeng ^a ^*

^aEngineering Research Center for Clean Production of Textile Dyeing and Printing, Ministry of Education, Wuhan 430073, People's Republic of China
^*Correspondence e-mail: qfzeng@wuse.edu.cn

(Received 14 August 2009; accepted 15 August 2009; online 22 August 2009)

In the title compound, [Fe(C₁₄H₁₂NOSe₂)₂], the Fe^II ion (site symmetry $[\overline{1}]$ ) is four-coordinated by two N,O-bidentate Schiff base ligands, resulting in a slightly distorted trans-FeN₂O₂ square-planar coordination for the metal ion.

Related literature

For background, see: Shi et al. (2008 ); Xu et al. (2009 ). For reference structural data, see: Allen et al. (1987 ).

Experimental

Crystal data

[Fe(C₁₄H₁₂NOSe₂)₂]
M_r = 792.18
Monoclinic, P 2₁ /c
a = 10.6065 (5) Å
b = 6.1055 (5) Å
c = 20.7125 (15) Å
β = 102.435 (5)°
V = 1309.83 (16) Å³
Z = 2
Mo Kα radiation
μ = 6.16 mm⁻¹
T = 296 K
0.32 × 0.26 × 0.24 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.243, T_max = 0.319 (expected range = 0.174–0.228)
8208 measured reflections
3231 independent reflections
2133 reflections with I > 2σ(I)
R_int = 0.044
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.105
S = 1.05
3231 reflections
175 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.68 e Å⁻³
Δρ_min = −0.61 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Fe1—O1	1.845 (2)
Fe1—N1	1.945 (3)

O1—Fe1—N1	91.85 (12)

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); 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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809032413/hb5048sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809032413/hb5048Isup2.hkl

checkCIF report

Comment top

There has been much research interest in Schiff base metal complexes due to their molecular architectures and biological activities (Shi et al., 2008; Xu et al., 2009). In this work, we report here the crystal structure of the title compound, (I). In (I), all bond lengths are within normal ranges (Allen et al., 1987) (Fig. 1). The Fe^II is four-coordinated in a slightly distort square-planar configuration by two N atoms and two O atoms of the Schiff base ligands.

Related literature top

For background, see: Shi et al. (2008); Xu et al. (2009). For reference structural data, see: Allen et al. (1987).

Experimental top

A mixture of 3,5-dihydroseleno-2-hydroxybenzaldehyde (564 mg, 2 mmol), phenylmethanamine (107 mg, 2 mmol) and FeCl₂.4H₂O (1 mmol, 198 mg) in methanol (10 ml) was stirred for 1 h. After keeping the filtrate in air for 7 d, green blocks of (I) were formed.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); 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 top

Fig. 1. The molecular structure of (I) showing 30% probability displacement ellipsoids, Atoms with an A suffix to their labels are generated by the symmetry operation (1–x, 1–y, –z).

Bis(2-benzyliminomethyl-4,6-dihydroselenophenolato)iron(II) top

Crystal data top

[Fe(C₁₄H₁₂NOSe₂)₂]	F(000) = 768
M_r = 792.18	D_x = 2.009 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 10.6065 (5) Å	θ = 9–12°
b = 6.1055 (5) Å	µ = 6.16 mm⁻¹
c = 20.7125 (15) Å	T = 296 K
β = 102.435 (5)°	Block, green
V = 1309.83 (16) Å³	0.32 × 0.26 × 0.24 mm
Z = 2

Data collection top

Enraf–Nonius CAD-4 diffractometer	2133 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.044
Graphite monochromator	θ_max = 28.6°, θ_min = 2.0°
ω/2θ scans	h = −13→12
Absorption correction: ψ scan (North et al., 1968)	k = −8→8
T_min = 0.243, T_max = 0.319	l = −27→24
8208 measured reflections	3 standard reflections every 200 reflections
3231 independent reflections	intensity decay: 1%

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0464P)²] where P = (F_o² + 2F_c²)/3
3231 reflections	(Δ/σ)_max = 0.015
175 parameters	Δρ_max = 0.68 e Å⁻³
2 restraints	Δρ_min = −0.61 e Å⁻³

Crystal data top

[Fe(C₁₄H₁₂NOSe₂)₂]	V = 1309.83 (16) Å³
M_r = 792.18	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.6065 (5) Å	µ = 6.16 mm⁻¹
b = 6.1055 (5) Å	T = 296 K
c = 20.7125 (15) Å	0.32 × 0.26 × 0.24 mm
β = 102.435 (5)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2133 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.044
T_min = 0.243, T_max = 0.319	3 standard reflections every 200 reflections
8208 measured reflections	intensity decay: 1%
3231 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	2 restraints
wR(F²) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.68 e Å⁻³
3231 reflections	Δρ_min = −0.61 e Å⁻³
175 parameters

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

	x	y	z	U_iso*/U_eq
Fe1	0.5000	0.5000	0.0000	0.02627 (19)
Se1	0.39624 (5)	1.46692 (8)	0.19627 (3)	0.06046 (19)
Se2	0.11313 (4)	0.76022 (9)	0.06333 (3)	0.05734 (19)
N1	0.6354 (3)	0.6850 (5)	0.05035 (16)	0.0338 (7)
O1	0.3733 (2)	0.6579 (5)	0.02791 (13)	0.0383 (7)
C3	0.6153 (4)	0.8701 (7)	0.0771 (2)	0.0370 (9)
H3	0.6877	0.9562	0.0930	0.044*
C4	0.4943 (3)	0.9565 (6)	0.08496 (19)	0.0333 (9)
C5	0.8814 (4)	0.1903 (9)	0.2276 (2)	0.0519 (12)
H5	0.9044	0.0960	0.2635	0.062*
C6	0.3792 (3)	0.8364 (6)	0.06265 (18)	0.0322 (9)
C7	0.8111 (3)	0.4726 (6)	0.12025 (19)	0.0339 (9)
C8	0.8905 (4)	0.2934 (7)	0.1180 (2)	0.0433 (10)
H8	0.9206	0.2664	0.0798	0.052*
C9	0.3884 (4)	1.2227 (6)	0.1388 (2)	0.0393 (9)
C10	0.2727 (4)	1.1107 (7)	0.11830 (19)	0.0403 (10)
H10	0.1978	1.1635	0.1293	0.048*
C12	0.7746 (3)	0.6234 (7)	0.0611 (2)	0.0359 (9)
H12A	0.8275	0.7544	0.0684	0.043*
H12B	0.7905	0.5504	0.0220	0.043*
C13	0.2689 (4)	0.9232 (7)	0.08202 (19)	0.0370 (9)
C14	0.4963 (4)	1.1457 (6)	0.1226 (2)	0.0398 (10)
H14	0.5737	1.2204	0.1368	0.048*
C15	0.7687 (4)	0.5074 (7)	0.1783 (2)	0.0425 (10)
H15	0.7167	0.6274	0.1820	0.051*
C16	0.8040 (4)	0.3632 (8)	0.2308 (2)	0.0504 (12)
H16	0.7734	0.3864	0.2691	0.061*
C17	0.9257 (4)	0.1547 (8)	0.1713 (2)	0.0498 (11)
H17	0.9798	0.0364	0.1689	0.060*
H1	0.318 (3)	1.461 (7)	0.2300 (18)	0.060*
H2	0.064 (4)	0.795 (7)	0.1091 (14)	0.060*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.0184 (3)	0.0306 (4)	0.0295 (4)	−0.0017 (3)	0.0046 (3)	−0.0018 (3)
Se1	0.0802 (4)	0.0432 (3)	0.0599 (4)	0.0061 (2)	0.0195 (3)	−0.0142 (2)
Se2	0.0286 (2)	0.0838 (4)	0.0631 (4)	−0.0073 (2)	0.0177 (2)	−0.0260 (3)
N1	0.0228 (15)	0.0406 (19)	0.0364 (19)	0.0003 (13)	0.0028 (13)	0.0025 (15)
O1	0.0262 (13)	0.0458 (17)	0.0436 (17)	−0.0017 (11)	0.0092 (12)	−0.0112 (14)
C3	0.0283 (19)	0.035 (2)	0.047 (3)	−0.0040 (16)	0.0069 (18)	0.004 (2)
C4	0.0310 (19)	0.032 (2)	0.037 (2)	−0.0006 (15)	0.0079 (17)	0.0007 (18)
C5	0.047 (3)	0.066 (3)	0.039 (3)	0.003 (2)	0.000 (2)	0.006 (2)
C6	0.0314 (19)	0.035 (2)	0.030 (2)	0.0012 (16)	0.0070 (16)	0.0023 (18)
C7	0.0201 (16)	0.044 (2)	0.035 (2)	−0.0050 (16)	−0.0009 (15)	−0.0045 (18)
C8	0.037 (2)	0.055 (3)	0.038 (2)	0.0061 (19)	0.0076 (18)	−0.005 (2)
C9	0.051 (2)	0.034 (2)	0.035 (2)	0.0071 (18)	0.0113 (19)	0.0010 (18)
C10	0.040 (2)	0.048 (3)	0.035 (2)	0.0138 (19)	0.0132 (19)	0.006 (2)
C12	0.0211 (17)	0.041 (2)	0.046 (2)	−0.0033 (15)	0.0070 (17)	−0.0012 (19)
C13	0.033 (2)	0.046 (3)	0.034 (2)	0.0039 (17)	0.0106 (17)	0.0013 (19)
C14	0.042 (2)	0.034 (2)	0.043 (2)	−0.0020 (18)	0.0059 (19)	0.003 (2)
C15	0.040 (2)	0.046 (3)	0.041 (3)	0.0009 (19)	0.0073 (19)	−0.011 (2)
C16	0.048 (3)	0.072 (3)	0.030 (2)	−0.009 (2)	0.007 (2)	−0.005 (2)
C17	0.046 (2)	0.054 (3)	0.046 (3)	0.010 (2)	0.003 (2)	0.003 (2)

Geometric parameters (Å, º) top

Fe1—O1	1.845 (2)	C6—C13	1.419 (5)
Fe1—O1ⁱ	1.845 (2)	C7—C8	1.387 (5)
Fe1—N1ⁱ	1.945 (3)	C7—C15	1.388 (5)
Fe1—N1	1.945 (3)	C7—C12	1.516 (5)
Se1—C9	1.898 (4)	C8—C17	1.378 (6)
Se1—H1	1.191 (10)	C8—H8	0.9300
Se2—C13	1.896 (4)	C9—C14	1.345 (5)
Se2—H2	1.196 (10)	C9—C10	1.390 (6)
N1—C3	1.296 (5)	C10—C13	1.365 (6)
N1—C12	1.493 (4)	C10—H10	0.9300
O1—C6	1.300 (4)	C12—H12A	0.9700
C3—C4	1.429 (5)	C12—H12B	0.9700
C3—H3	0.9300	C14—H14	0.9300
C4—C14	1.391 (5)	C15—C16	1.387 (6)
C4—C6	1.414 (5)	C15—H15	0.9300
C5—C16	1.348 (6)	C16—H16	0.9300
C5—C17	1.366 (6)	C17—H17	0.9300
C5—H5	0.9300

O1—Fe1—O1ⁱ	180.0	C7—C8—H8	119.3
O1—Fe1—N1ⁱ	88.15 (12)	C14—C9—C10	119.6 (4)
O1ⁱ—Fe1—N1ⁱ	91.85 (12)	C14—C9—Se1	120.5 (3)
O1—Fe1—N1	91.85 (12)	C10—C9—Se1	119.7 (3)
O1ⁱ—Fe1—N1	88.15 (12)	C13—C10—C9	120.1 (4)
N1ⁱ—Fe1—N1	180.0	C13—C10—H10	120.0
C9—Se1—H1	114 (2)	C9—C10—H10	120.0
C13—Se2—H2	105 (2)	N1—C12—C7	110.2 (3)
C3—N1—C12	113.9 (3)	N1—C12—H12A	109.6
C3—N1—Fe1	124.4 (3)	C7—C12—H12A	109.6
C12—N1—Fe1	121.7 (3)	N1—C12—H12B	109.6
C6—O1—Fe1	131.3 (2)	C7—C12—H12B	109.6
N1—C3—C4	127.2 (4)	H12A—C12—H12B	108.1
N1—C3—H3	116.4	C10—C13—C6	122.7 (4)
C4—C3—H3	116.4	C10—C13—Se2	118.3 (3)
C14—C4—C6	121.4 (3)	C6—C13—Se2	118.8 (3)
C14—C4—C3	117.7 (3)	C9—C14—C4	121.3 (4)
C6—C4—C3	120.4 (3)	C9—C14—H14	119.4
C16—C5—C17	119.4 (4)	C4—C14—H14	119.4
C16—C5—H5	120.3	C16—C15—C7	119.9 (4)
C17—C5—H5	120.3	C16—C15—H15	120.0
O1—C6—C4	123.4 (3)	C7—C15—H15	120.0
O1—C6—C13	121.7 (3)	C5—C16—C15	121.6 (4)
C4—C6—C13	114.9 (4)	C5—C16—H16	119.2
C8—C7—C15	117.5 (4)	C15—C16—H16	119.2
C8—C7—C12	120.2 (3)	C5—C17—C8	120.2 (4)
C15—C7—C12	122.2 (3)	C5—C17—H17	119.9
C17—C8—C7	121.3 (4)	C8—C17—H17	119.9
C17—C8—H8	119.3

Symmetry code: (i) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	[Fe(C₁₄H₁₂NOSe₂)₂]
M_r	792.18
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	10.6065 (5), 6.1055 (5), 20.7125 (15)
β (°)	102.435 (5)
V (Å³)	1309.83 (16)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	6.16
Crystal size (mm)	0.32 × 0.26 × 0.24

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.243, 0.319
No. of measured, independent and observed [I > 2σ(I)] reflections	8208, 3231, 2133
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.672

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.105, 1.05
No. of reflections	3231
No. of parameters	175
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.68, −0.61

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Fe1—O1	1.845 (2)	Fe1—N1	1.945 (3)

O1—Fe1—N1	91.85 (12)

Acknowledgements

The project was supported by the Scientific Research Foundation for Returned Overseas Chinese Scholars, State Education Ministry, Educational Commission of Hubei Province (D20091703) and the Natural Science Foundation of Hubei Province (2008CDB038).

References

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