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The title complex, trans,trans,trans-[FeII(C10H6NO2)2(C2H6O)2], is centrosymmetric and the quinaldinate ligands form five-membered chelate rings. The geometry of the complex is distorted octahedral, with a trans-FeN2O4 chromo­phore. The hydroxy H atom forms an intermolecular hydrogen bond with the carbonyl O atom of the quinaldinate ligand.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803009607/tk6101sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803009607/tk6101Isup2.hkl
Contains datablock I

CCDC reference: 214772

Key indicators

  • Single-crystal X-ray study
  • T = 123 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.039
  • wR factor = 0.069
  • Data-to-parameter ratio = 16.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
PLAT_712 Alert C ANGLE Unknown or Inconsistent Label ........ FE1 FE1 O1 C1 PLAT_712 Alert C ANGLE Unknown or Inconsistent Label ........ FE1 FE1 O3 C11 PLAT_712 Alert C ANGLE Unknown or Inconsistent Label ........ FE1 FE1 O3 H7 PLAT_712 Alert C ANGLE Unknown or Inconsistent Label ........ FE1 FE1 N1 C2 PLAT_712 Alert C ANGLE Unknown or Inconsistent Label ........ FE1 FE1 N1 C10 PLAT_713 Alert C TORSION Unknown or Inconsistent Label ........ FE1 FE1 O1 C1 O2 PLAT_713 Alert C TORSION Unknown or Inconsistent Label ........ FE1 FE1 O1 C1 C2 PLAT_713 Alert C TORSION Unknown or Inconsistent Label ........ FE1 FE1 O3 C11 C12 PLAT_713 Alert C TORSION Unknown or Inconsistent Label ........ FE1 FE1 N1 C2 C1 PLAT_713 Alert C TORSION Unknown or Inconsistent Label ........ FE1 FE1 N1 C2 C3 PLAT_713 Alert C TORSION Unknown or Inconsistent Label ........ FE1 FE1 N1 C10 C5 PLAT_713 Alert C TORSION Unknown or Inconsistent Label ........ FE1 FE1 N1 C10 C9 PLAT_713 Alert C TORSION Unknown or Inconsistent Label ........ FE1 O1 FE1 O3 C11 PLAT_713 Alert C TORSION Unknown or Inconsistent Label ........ FE1 O1 FE1 N1 C2 PLAT_713 Alert C TORSION Unknown or Inconsistent Label ........ FE1 O1 FE1 N1 C10 PLAT_713 Alert C TORSION Unknown or Inconsistent Label ........ FE1 O3 FE1 O1 C1 PLAT_713 Alert C TORSION Unknown or Inconsistent Label ........ FE1 O3 FE1 N1 C2 PLAT_713 Alert C TORSION Unknown or Inconsistent Label ........ FE1 O3 FE1 N1 C10 PLAT_713 Alert C TORSION Unknown or Inconsistent Label ........ FE1 N1 FE1 O1 C1 PLAT_713 Alert C TORSION Unknown or Inconsistent Label ........ FE1 N1 FE1 O3 C11
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
20 Alert Level C = Please check

Comment top

Quinaldic acid is associated with tryptophan metabolism (Zhou et al., 1989) and is used as a reagent for solvent extraction of divalent transition metal ions (Högberg et al., 1985). There are few structural studies of quialdinate complexes in spite of numerous studies of related picolinato complexes. Only the Cu2+ (Hanendler, 1986), Rh+ (Lamprecht et al., 1986) and Ga3+ (Li et al., 1996) complexes have been structurally characterized. Therefore, structural information of another transition metal ion is desired.

The title complex, (I), is monomeric and has a distorted octahedral structure, with the central atom lying on an inversion center (Fig. 1 and Table 1). The complex has a trans,trans,trans-geometry with respect to three kinds of donors. The quinaldinate acts as a planar N,O-bidentate ligand and forms a five-membered chelate ring upon coordination. Two quinaldinato ligands are connected with weak intramolecular hydrogen bonds; the distance between atoms C9 and O1i is 3.152 (3) Å [symmetry code: (i) −x, 1 − y,-z].

There exists a strong hydrogen bond between an ethanol molecule and the uncoordinated O atom of a neighbouring quinaldinate ligand. The distance between atoms O3 and O2ii is 2.694 (3) Å [symmetry code: (ii) 1 − x, 1 − y, −z]. The hydrogen bonds form one-dimensional molecular chains parallel to the a axis. The chains are connected by weak hydrogen bonds (Table 2).

Experimental top

The title complex was prepared under an N2 atmosphere using Schlenk techniques. To a solution of Fe(BF4)2·6H2O (0.134 g, 0.397 mmol) in 1.6 ml e thanol was added a solution containing quinaldic acid (0.173 g, 0.999 mmol) in ethanol (6 ml) and trietylamine (140 ml, 0.100 mmol). After vigorous stirring, the solution was allowed to stand for 2 d to afford red–violet crystals suitable for X-ray analysis. The IR spectrum showed a ν(CO2) band at 1628 cm−1. The electronic spectrum in DMF exhibits an absorption maximum at 527 nm (ε = 795).

Refinement top

H atoms were included at calculated positions (0.96 Å), with isotropic displacement parameters of 1.2Ueq(parent atom).

Computing details top

Data collection: CrystalClear (Molecular Structure Corporation/Rigaku, 2001); cell refinement: CrystalClear; data reduction: TEXSAN (Molecular Structure Corporation/Rigaku, 2000); program(s) used to solve structure: SHELXS86 (Sheldrick, 1985); program(s) used to refine structure: TEXSAN; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: TEXSAN.

Figures top
[Figure 1] Fig. 1. ORTEP-3 drawing (Farrugia, 1997) of (I), half of which defines the asymmetric unit, showing the atomic numbering scheme. Displacement ellipsoids for the non-H atoms are shown at the 50% probability level.
[Figure 2] Fig. 2. Packing diagram of the title complex. Dotted lines show hydrogen bonding, which forms molecular chains parallel to the a axis.
(I) top
Crystal data top
[Fe(C10H6NO2)2(C2H6O)2]F(000) = 512
Mr = 492.30Dx = 1.475 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ynCell parameters from 4502 reflections
a = 5.816 (2) Åθ = 3.1–27.5°
b = 9.557 (3) ŵ = 0.72 mm1
c = 19.948 (5) ÅT = 123 K
β = 91.461 (7)°Prism, red-violet
V = 1108.4 (6) Å30.20 × 0.05 × 0.05 mm
Z = 2
Data collection top
Rigaku/MSC Mercury CCD
diffractometer
2006 reflections with F2 > 2σ(F2)
Detector resolution: 14.62 pixels mm-1Rint = 0.039
ω scansθmax = 27.5°
Absorption correction: multi-scan
(Jacobson, 1998)
h = 77
Tmin = 0.783, Tmax = 0.964k = 1212
8886 measured reflectionsl = 2525
2511 independent reflections
Refinement top
Refinement on FH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.039 w = 1/[σ2(Fo) + 0.00168|Fo|2]
wR(F2) = 0.069(Δ/σ)max < 0.001
S = 1.07Δρmax = 0.33 e Å3
2506 reflectionsΔρmin = 0.27 e Å3
151 parameters
Crystal data top
[Fe(C10H6NO2)2(C2H6O)2]V = 1108.4 (6) Å3
Mr = 492.30Z = 2
Monoclinic, P21/nMo Kα radiation
a = 5.816 (2) ŵ = 0.72 mm1
b = 9.557 (3) ÅT = 123 K
c = 19.948 (5) Å0.20 × 0.05 × 0.05 mm
β = 91.461 (7)°
Data collection top
Rigaku/MSC Mercury CCD
diffractometer
2511 independent reflections
Absorption correction: multi-scan
(Jacobson, 1998)
2006 reflections with F2 > 2σ(F2)
Tmin = 0.783, Tmax = 0.964Rint = 0.039
8886 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.039151 parameters
wR(F2) = 0.069H-atom parameters constrained
S = 1.07Δρmax = 0.33 e Å3
2506 reflectionsΔρmin = 0.27 e Å3
Special details top

Refinement. Refinement using reflections with F2 > 0.0 σ(F2). The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative 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
Fe0.00000.50000.00000.0124 (1)
O10.2962 (3)0.5645 (2)0.04657 (9)0.0163 (5)
O20.5102 (3)0.5625 (2)0.14098 (9)0.0187 (5)
O30.1775 (3)0.3408 (2)0.0549 (1)0.0222 (5)
N10.0041 (4)0.3768 (2)0.0955 (1)0.0133 (5)
C10.3426 (4)0.5231 (3)0.1055 (1)0.0142 (6)
C20.1781 (4)0.4176 (3)0.1355 (1)0.0150 (6)
C30.2155 (5)0.3673 (3)0.2011 (1)0.0189 (7)
C40.0674 (5)0.2709 (3)0.2259 (1)0.0186 (7)
C50.1196 (5)0.2224 (3)0.1852 (1)0.0161 (6)
C60.2785 (5)0.1198 (3)0.2075 (1)0.0194 (7)
C70.4522 (5)0.0759 (3)0.1655 (1)0.0209 (7)
C80.4797 (5)0.1324 (3)0.1004 (1)0.0190 (7)
C90.3308 (5)0.2325 (3)0.0773 (1)0.0181 (7)
C100.1463 (4)0.2783 (3)0.1193 (1)0.0148 (6)
C110.1449 (5)0.1934 (3)0.0572 (2)0.0232 (7)
C120.0132 (6)0.1495 (4)0.1137 (2)0.0386 (10)
H10.34340.40030.22810.0227*
H20.08950.23590.27070.0224*
H30.26320.08190.25200.0233*
H40.55730.00560.18030.0250*
H50.60410.10060.07170.0228*
H60.35210.27090.03310.0217*
H70.29850.37500.08240.0267*
H80.08090.16350.01570.0278*
H90.29150.14920.06270.0278*
H100.16070.19270.10860.0463*
H110.05000.17790.15550.0463*
H120.03050.04960.11320.0463*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe0.0144 (3)0.0130 (3)0.0097 (3)0.0022 (2)0.0006 (2)0.0002 (2)
O10.0147 (8)0.021 (1)0.0130 (9)0.0040 (8)0.0011 (7)0.0016 (8)
O20.0158 (9)0.025 (1)0.0152 (9)0.0049 (8)0.0003 (7)0.0019 (8)
O30.0197 (9)0.019 (1)0.028 (1)0.0048 (8)0.0090 (8)0.0074 (9)
N10.0156 (10)0.013 (1)0.012 (1)0.0006 (8)0.0006 (8)0.0004 (8)
C10.014 (1)0.011 (1)0.018 (1)0.0014 (9)0.0026 (9)0.0025 (10)
C20.015 (1)0.015 (1)0.015 (1)0.002 (1)0.0029 (9)0.002 (1)
C30.019 (1)0.023 (1)0.015 (1)0.002 (1)0.003 (1)0.001 (1)
C40.026 (1)0.017 (1)0.012 (1)0.003 (1)0.000 (1)0.002 (1)
C50.019 (1)0.016 (1)0.013 (1)0.002 (1)0.0038 (10)0.001 (1)
C60.025 (1)0.017 (1)0.016 (1)0.001 (1)0.005 (1)0.006 (1)
C70.024 (1)0.014 (1)0.024 (1)0.003 (1)0.005 (1)0.006 (1)
C80.019 (1)0.019 (1)0.019 (1)0.002 (1)0.000 (1)0.002 (1)
C90.021 (1)0.017 (1)0.016 (1)0.001 (1)0.001 (1)0.002 (1)
C100.015 (1)0.013 (1)0.017 (1)0.0006 (10)0.0034 (10)0.000 (1)
C110.025 (1)0.016 (1)0.028 (2)0.001 (1)0.003 (1)0.002 (1)
C120.033 (2)0.027 (2)0.055 (2)0.004 (1)0.009 (2)0.020 (2)
Geometric parameters (Å, º) top
Fe—O12.032 (2)C5—C101.425 (4)
Fe—O32.154 (2)C6—C71.363 (4)
Fe—N12.240 (2)C6—H30.960
O1—C11.263 (3)C7—C81.412 (4)
O2—C11.248 (3)C7—H40.960
O3—C111.422 (4)C8—C91.377 (4)
O3—H70.960C8—H50.960
N1—C21.331 (3)C9—C101.413 (4)
N1—C101.376 (4)C9—H60.960
C1—C21.523 (4)C11—C121.496 (4)
C2—C31.406 (4)C11—H80.960
C3—C41.363 (4)C11—H90.960
C3—H10.960C12—H100.960
C4—C51.418 (4)C12—H110.960
C4—H20.960C12—H120.960
C5—C61.426 (4)
O1···O3i3.192 (3)O2···C9iii3.532 (4)
O1···O1i3.289 (4)O3···C1i3.263 (3)
O2···O3i2.694 (3)C1···C9iii3.420 (4)
O2···C4ii3.359 (3)C2···C8iii3.457 (4)
O2···C10iii3.406 (3)C2···C9iii3.578 (4)
O2···C6ii3.410 (3)C3···C7iii3.473 (4)
O2···N1iii3.515 (3)C3···C8iii3.522 (4)
O2···C11i3.525 (4)C4···C7iii3.592 (4)
O1—Fe—O392.01 (8)C5—C6—H3120.1
O1—Fe—N177.30 (8)C7—C6—H3120.1
O3—Fe—N193.82 (8)C6—C7—C8120.9 (3)
FE1—O1—C1119.3 (2)C6—C7—H4119.6
FE1—O3—C11130.6 (2)C8—C7—H4119.6
FE1—O3—H7114.7C7—C8—C9121.0 (2)
C11—O3—H7114.7C7—C8—H5119.5
FE1—N1—C2110.3 (2)C9—C8—H5119.5
FE1—N1—C10131.2 (2)C8—C9—C10119.5 (2)
C2—N1—C10118.3 (2)C8—C9—H6120.3
O1—C1—O2125.3 (2)C10—C9—H6120.3
O1—C1—C2116.8 (2)N1—C10—C5121.2 (2)
O2—C1—C2117.8 (2)N1—C10—C9119.2 (2)
N1—C2—C1115.8 (2)C5—C10—C9119.6 (2)
N1—C2—C3123.7 (2)O3—C11—C12112.4 (3)
C1—C2—C3120.5 (2)O3—C11—H8108.7
C2—C3—C4119.0 (2)O3—C11—H9108.7
C2—C3—H1120.5C12—C11—H8108.7
C4—C3—H1120.5C12—C11—H9108.7
C3—C4—C5119.7 (2)H8—C11—H9109.5
C3—C4—H2120.1C11—C12—H10109.5
C5—C4—H2120.1C11—C12—H11109.5
C4—C5—C6122.6 (2)C11—C12—H12109.5
C4—C5—C10118.0 (2)H10—C12—H11109.5
C6—C5—C10119.3 (2)H10—C12—H12109.5
C5—C6—C7119.7 (3)H11—C12—H12109.5
FE1—O1—C1—O2174.9 (2)N1—C10—C5—C40.2 (4)
FE1—O1—C1—C24.5 (3)N1—C10—C5—C6179.5 (2)
FE1—O3—C11—C1293.2 (3)N1—C10—C9—C8179.0 (3)
FE1—N1—C2—C16.0 (3)C1—C2—N1—C10178.1 (2)
FE1—N1—C2—C3175.0 (2)C1—C2—C3—C4178.7 (2)
FE1—N1—C10—C5174.0 (2)C2—N1—C10—C50.9 (4)
FE1—N1—C10—C95.8 (4)C2—N1—C10—C9179.3 (2)
O1—FE1—O3—C11122.1 (2)C2—C3—C4—C50.5 (4)
O1—FE1—N1—C26.3 (2)C3—C2—N1—C100.9 (4)
O1—FE1—N1—C10178.5 (2)C3—C4—C5—C6178.8 (3)
O1—C1—C2—N11.7 (3)C3—C4—C5—C100.5 (4)
O1—C1—C2—C3179.3 (2)C4—C5—C6—C7178.8 (3)
O2—C1—C2—N1178.9 (2)C4—C5—C10—C9180.0 (3)
O2—C1—C2—C30.1 (4)C5—C6—C7—C81.1 (4)
O3—FE1—O1—C199.3 (2)C5—C10—C9—C81.2 (4)
O3—FE1—N1—C297.5 (2)C6—C5—C10—C90.7 (4)
O3—FE1—N1—C1087.3 (2)C6—C7—C8—C90.6 (5)
N1—FE1—O1—C15.9 (2)C7—C6—C5—C100.5 (4)
N1—FE1—O3—C1144.7 (2)C7—C8—C9—C100.6 (4)
N1—C2—C3—C40.2 (4)C7—C8—C9—C100.6 (4)
Symmetry codes: (i) x+1, y+1, z; (ii) x+1/2, y+1/2, z+1/2; (iii) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H6···O1iv0.962.273.152 (3)153
O3—H7···O1i0.962.513.192 (3)128
O3—H7···O2i0.961.742.694 (3)172
C4—H2···O2v0.962.503.359 (3)149
C6—H3···O2v0.962.573.410 (3)146
Symmetry codes: (i) x+1, y+1, z; (iv) x, y+1, z; (v) x+1/2, y1/2, z+1/2.

Experimental details

Crystal data
Chemical formula[Fe(C10H6NO2)2(C2H6O)2]
Mr492.30
Crystal system, space groupMonoclinic, P21/n
Temperature (K)123
a, b, c (Å)5.816 (2), 9.557 (3), 19.948 (5)
β (°) 91.461 (7)
V3)1108.4 (6)
Z2
Radiation typeMo Kα
µ (mm1)0.72
Crystal size (mm)0.20 × 0.05 × 0.05
Data collection
DiffractometerRigaku/MSC Mercury CCD
diffractometer
Absorption correctionMulti-scan
(Jacobson, 1998)
Tmin, Tmax0.783, 0.964
No. of measured, independent and
observed [F2 > 2σ(F2)] reflections
8886, 2511, 2006
Rint0.039
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.069, 1.07
No. of reflections2506
No. of parameters151
No. of restraints?
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.33, 0.27

Computer programs: CrystalClear (Molecular Structure Corporation/Rigaku, 2001), CrystalClear, TEXSAN (Molecular Structure Corporation/Rigaku, 2000), SHELXS86 (Sheldrick, 1985), TEXSAN, ORTEP-3 for Windows (Farrugia, 1997).

Selected geometric parameters (Å, º) top
Fe—O12.032 (2)Fe—N12.240 (2)
Fe—O32.154 (2)
O1—Fe—O392.01 (8)O3—Fe—N193.82 (8)
O1—Fe—N177.30 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H6···O1i0.962.273.152 (3)153
O3—H7···O1ii0.962.513.192 (3)128
O3—H7···O2ii0.961.742.694 (3)172
C4—H2···O2iii0.962.503.359 (3)149
C6—H3···O2iii0.962.573.410 (3)146
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1, z; (iii) x+1/2, y1/2, z+1/2.
 

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