trans,trans,trans-Diethano­ldiquinaldinatoiron(II)

The title complex, trans,trans,trans-[Fe^II(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.

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


 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

---

S1. Comment

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).

S2. Experimental

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).

S3. Refinement

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

Computing details

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

	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.
	Fig. 2. Packing diagram of the title complex. Dotted lines show hydrogen bonding, which forms molecular chains parallel to the a axis.

(I)

Crystal data

[Fe(C10H6NO2)2(C2H6O)2]	F(000) = 512
Mr = 492.30	Dx = 1.475 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2yn	Cell parameters from 4502 reflections
a = 5.816 (2) Å	θ = 3.1–27.5°
b = 9.557 (3) Å	µ = 0.72 mm^−1
c = 19.948 (5) Å	T = 123 K
β = 91.461 (7)°	Prism, red-violet
V = 1108.4 (6) Å^3	0.20 × 0.05 × 0.05 mm
Z = 2

Data collection

Rigaku/MSC Mercury CCD diffractometer	2006 reflections with F^2 > 2σ(F^2)
Detector resolution: 14.62 pixels mm^-1	Rint = 0.039
ω scans	θmax = 27.5°
Absorption correction: multi-scan (Jacobson, 1998)	h = −7→7
Tmin = 0.783, Tmax = 0.964	k = −12→12
8886 measured reflections	l = −25→25
2511 independent reflections

Refinement

Refinement on F	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.039	w = 1/[σ^2(Fo) + 0.00168|Fo|^2]
wR(F^2) = 0.069	(Δ/σ)max < 0.001
S = 1.07	Δρmax = 0.33 e Å^−3
2506 reflections	Δρmin = −0.27 e Å^−3
151 parameters

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Fe	0.0000	0.5000	0.0000	0.0124 (1)
O1	0.2962 (3)	0.5645 (2)	0.04657 (9)	0.0163 (5)
O2	0.5102 (3)	0.5625 (2)	0.14098 (9)	0.0187 (5)
O3	0.1775 (3)	0.3408 (2)	−0.0549 (1)	0.0222 (5)
N1	0.0041 (4)	0.3768 (2)	0.0955 (1)	0.0133 (5)
C1	0.3426 (4)	0.5231 (3)	0.1055 (1)	0.0142 (6)
C2	0.1781 (4)	0.4176 (3)	0.1355 (1)	0.0150 (6)
C3	0.2155 (5)	0.3673 (3)	0.2011 (1)	0.0189 (7)
C4	0.0674 (5)	0.2709 (3)	0.2259 (1)	0.0186 (7)
C5	−0.1196 (5)	0.2224 (3)	0.1852 (1)	0.0161 (6)
C6	−0.2785 (5)	0.1198 (3)	0.2075 (1)	0.0194 (7)
C7	−0.4522 (5)	0.0759 (3)	0.1655 (1)	0.0209 (7)
C8	−0.4797 (5)	0.1324 (3)	0.1004 (1)	0.0190 (7)
C9	−0.3308 (5)	0.2325 (3)	0.0773 (1)	0.0181 (7)
C10	−0.1463 (4)	0.2783 (3)	0.1193 (1)	0.0148 (6)
C11	0.1449 (5)	0.1934 (3)	−0.0572 (2)	0.0232 (7)
C12	−0.0132 (6)	0.1495 (4)	−0.1137 (2)	0.0386 (10)
H1	0.3434	0.4003	0.2281	0.0227*
H2	0.0895	0.2359	0.2707	0.0224*
H3	−0.2632	0.0819	0.2520	0.0233*
H4	−0.5573	0.0056	0.1803	0.0250*
H5	−0.6041	0.1006	0.0717	0.0228*
H6	−0.3521	0.2709	0.0331	0.0217*
H7	0.2985	0.3750	−0.0824	0.0267*
H8	0.0809	0.1635	−0.0157	0.0278*
H9	0.2915	0.1492	−0.0627	0.0278*
H10	−0.1607	0.1927	−0.1086	0.0463*
H11	0.0500	0.1779	−0.1555	0.0463*
H12	−0.0305	0.0496	−0.1132	0.0463*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe	0.0144 (3)	0.0130 (3)	0.0097 (3)	−0.0022 (2)	−0.0006 (2)	0.0002 (2)
O1	0.0147 (8)	0.021 (1)	0.0130 (9)	−0.0040 (8)	−0.0011 (7)	0.0016 (8)
O2	0.0158 (9)	0.025 (1)	0.0152 (9)	−0.0049 (8)	−0.0003 (7)	−0.0019 (8)
O3	0.0197 (9)	0.019 (1)	0.028 (1)	−0.0048 (8)	0.0090 (8)	−0.0074 (9)
N1	0.0156 (10)	0.013 (1)	0.012 (1)	0.0006 (8)	0.0006 (8)	−0.0004 (8)
C1	0.014 (1)	0.011 (1)	0.018 (1)	0.0014 (9)	0.0026 (9)	−0.0025 (10)
C2	0.015 (1)	0.015 (1)	0.015 (1)	0.002 (1)	0.0029 (9)	−0.002 (1)
C3	0.019 (1)	0.023 (1)	0.015 (1)	0.002 (1)	−0.003 (1)	−0.001 (1)
C4	0.026 (1)	0.017 (1)	0.012 (1)	0.003 (1)	0.000 (1)	0.002 (1)
C5	0.019 (1)	0.016 (1)	0.013 (1)	0.002 (1)	0.0038 (10)	0.001 (1)
C6	0.025 (1)	0.017 (1)	0.016 (1)	0.001 (1)	0.005 (1)	0.006 (1)
C7	0.024 (1)	0.014 (1)	0.024 (1)	−0.003 (1)	0.005 (1)	0.006 (1)
C8	0.019 (1)	0.019 (1)	0.019 (1)	−0.002 (1)	0.000 (1)	0.002 (1)
C9	0.021 (1)	0.017 (1)	0.016 (1)	−0.001 (1)	0.001 (1)	0.002 (1)
C10	0.015 (1)	0.013 (1)	0.017 (1)	0.0006 (10)	0.0034 (10)	0.000 (1)
C11	0.025 (1)	0.016 (1)	0.028 (2)	0.001 (1)	0.003 (1)	−0.002 (1)
C12	0.033 (2)	0.027 (2)	0.055 (2)	0.004 (1)	−0.009 (2)	−0.020 (2)

Geometric parameters (Å, º)

Fe—O1	2.032 (2)	C5—C10	1.425 (4)
Fe—O3	2.154 (2)	C6—C7	1.363 (4)
Fe—N1	2.240 (2)	C6—H3	0.960
O1—C1	1.263 (3)	C7—C8	1.412 (4)
O2—C1	1.248 (3)	C7—H4	0.960
O3—C11	1.422 (4)	C8—C9	1.377 (4)
O3—H7	0.960	C8—H5	0.960
N1—C2	1.331 (3)	C9—C10	1.413 (4)
N1—C10	1.376 (4)	C9—H6	0.960
C1—C2	1.523 (4)	C11—C12	1.496 (4)
C2—C3	1.406 (4)	C11—H8	0.960
C3—C4	1.363 (4)	C11—H9	0.960
C3—H1	0.960	C12—H10	0.960
C4—C5	1.418 (4)	C12—H11	0.960
C4—H2	0.960	C12—H12	0.960
C5—C6	1.426 (4)
O1···O3^i	3.192 (3)	O2···C9^iii	3.532 (4)
O1···O1^i	3.289 (4)	O3···C1^i	3.263 (3)
O2···O3^i	2.694 (3)	C1···C9^iii	3.420 (4)
O2···C4^ii	3.359 (3)	C2···C8^iii	3.457 (4)
O2···C10^iii	3.406 (3)	C2···C9^iii	3.578 (4)
O2···C6^ii	3.410 (3)	C3···C7^iii	3.473 (4)
O2···N1^iii	3.515 (3)	C3···C8^iii	3.522 (4)
O2···C11^i	3.525 (4)	C4···C7^iii	3.592 (4)
O1—Fe—O3	92.01 (8)	C5—C6—H3	120.1
O1—Fe—N1	77.30 (8)	C7—C6—H3	120.1
O3—Fe—N1	93.82 (8)	C6—C7—C8	120.9 (3)
FE1—O1—C1	119.3 (2)	C6—C7—H4	119.6
FE1—O3—C11	130.6 (2)	C8—C7—H4	119.6
FE1—O3—H7	114.7	C7—C8—C9	121.0 (2)
C11—O3—H7	114.7	C7—C8—H5	119.5
FE1—N1—C2	110.3 (2)	C9—C8—H5	119.5
FE1—N1—C10	131.2 (2)	C8—C9—C10	119.5 (2)
C2—N1—C10	118.3 (2)	C8—C9—H6	120.3
O1—C1—O2	125.3 (2)	C10—C9—H6	120.3
O1—C1—C2	116.8 (2)	N1—C10—C5	121.2 (2)
O2—C1—C2	117.8 (2)	N1—C10—C9	119.2 (2)
N1—C2—C1	115.8 (2)	C5—C10—C9	119.6 (2)
N1—C2—C3	123.7 (2)	O3—C11—C12	112.4 (3)
C1—C2—C3	120.5 (2)	O3—C11—H8	108.7
C2—C3—C4	119.0 (2)	O3—C11—H9	108.7
C2—C3—H1	120.5	C12—C11—H8	108.7
C4—C3—H1	120.5	C12—C11—H9	108.7
C3—C4—C5	119.7 (2)	H8—C11—H9	109.5
C3—C4—H2	120.1	C11—C12—H10	109.5
C5—C4—H2	120.1	C11—C12—H11	109.5
C4—C5—C6	122.6 (2)	C11—C12—H12	109.5
C4—C5—C10	118.0 (2)	H10—C12—H11	109.5
C6—C5—C10	119.3 (2)	H10—C12—H12	109.5
C5—C6—C7	119.7 (3)	H11—C12—H12	109.5
FE1—O1—C1—O2	−174.9 (2)	N1—C10—C5—C4	−0.2 (4)
FE1—O1—C1—C2	4.5 (3)	N1—C10—C5—C6	−179.5 (2)
FE1—O3—C11—C12	93.2 (3)	N1—C10—C9—C8	179.0 (3)
FE1—N1—C2—C1	−6.0 (3)	C1—C2—N1—C10	178.1 (2)
FE1—N1—C2—C3	175.0 (2)	C1—C2—C3—C4	−178.7 (2)
FE1—N1—C10—C5	−174.0 (2)	C2—N1—C10—C5	0.9 (4)
FE1—N1—C10—C9	5.8 (4)	C2—N1—C10—C9	−179.3 (2)
O1—FE1—O3—C11	122.1 (2)	C2—C3—C4—C5	0.5 (4)
O1—FE1—N1—C2	6.3 (2)	C3—C2—N1—C10	−0.9 (4)
O1—FE1—N1—C10	−178.5 (2)	C3—C4—C5—C6	178.8 (3)
O1—C1—C2—N1	1.7 (3)	C3—C4—C5—C10	−0.5 (4)
O1—C1—C2—C3	−179.3 (2)	C4—C5—C6—C7	−178.8 (3)
O2—C1—C2—N1	−178.9 (2)	C4—C5—C10—C9	−180.0 (3)
O2—C1—C2—C3	0.1 (4)	C5—C6—C7—C8	−1.1 (4)
O3—FE1—O1—C1	−99.3 (2)	C5—C10—C9—C8	−1.2 (4)
O3—FE1—N1—C2	97.5 (2)	C6—C5—C10—C9	0.7 (4)
O3—FE1—N1—C10	−87.3 (2)	C6—C7—C8—C9	0.6 (5)
N1—FE1—O1—C1	−5.9 (2)	C7—C6—C5—C10	0.5 (4)
N1—FE1—O3—C11	44.7 (2)	C7—C8—C9—C10	0.6 (4)
N1—C2—C3—C4	0.2 (4)	C7—C8—C9—C10	0.6 (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)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H6···O1^iv	0.96	2.27	3.152 (3)	153
O3—H7···O1^i	0.96	2.51	3.192 (3)	128
O3—H7···O2^i	0.96	1.74	2.694 (3)	172
C4—H2···O2^v	0.96	2.50	3.359 (3)	149
C6—H3···O2^v	0.96	2.57	3.410 (3)	146

Symmetry codes: (i) −x+1, −y+1, −z; (iv) −x, −y+1, −z; (v) −x+1/2, y−1/2, −z+1/2.