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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): m1585.
Published online 2010 November 17. doi:  10.1107/S1600536810046623
PMCID: PMC3011765

Dichlorido{1-[(2-hy­droxy­eth­yl)imino­meth­yl]-2-naphtho­lato}pyridine­iron(III) pyridine monosolvate

Abstract

In the title complex, [Fe(C13H12NO2)Cl2(C5H5N)]·C5H5N, the iron(III) atom is six-coordinated by the N and O atoms from the Schiff base ligand, the N atom from a pyridine mol­ecule and two chloride anions in a distorted octa­hedral geometry. The crystal packing is stabilized by inter­molecular O—H(...)N hydrogen bonds and C—H(...)π inter­actions.

Related literature

For the synthesis and applications of magnetic complexes, see: Oshio et al. (2004 [triangle]); Aromí & Brechin (2006 [triangle]). For related structures, see: Goodwin et al. (2000 [triangle]); Qian et al. (2008 [triangle]); Hoshino et al. (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1585-scheme1.jpg

Experimental

Crystal data

  • [Fe(C13H12NO2)Cl2(C5H5N)]·C5H5N
  • M r = 499.19
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1585-efi1.jpg
  • a = 7.8590 (6) Å
  • b = 10.0153 (11) Å
  • c = 14.4884 (16) Å
  • β = 90.123 (1)°
  • V = 1140.4 (2) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.92 mm−1
  • T = 298 K
  • 0.48 × 0.44 × 0.37 mm

Data collection

  • Bruker SMART 1000 CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Siemens, 1996 [triangle]) T min = 0.666, T max = 0.727
  • 5726 measured reflections
  • 3395 independent reflections
  • 3143 reflections with I > 2σ(I)
  • R int = 0.021

Refinement

  • R[F 2 > 2σ(F 2)] = 0.032
  • wR(F 2) = 0.085
  • S = 1.00
  • 3395 reflections
  • 281 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.25 e Å−3
  • Δρmin = −0.19 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 1265 Friedel pairs
  • Flack parameter: 0.02 (2)

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810046623/rz2519sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810046623/rz2519Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

This work was supported by the National Natural Science Foundation of China (No. 20671048, 21041002)

supplementary crystallographic information

Comment

The considerable current interest in magnetic complexes arises from their relevance in diverse fields ranging from bioinorganic chemistry to molecular magnetic materials (Oshio et al., 2004; Aromí et al., 2006). We report here the synthesis and crystal structure of the title compound.

In the title complex (Fig. 1), the tridentate Schiff base ligand is derived from the condensation of 2-hydroxy-1-naphthaldehyde and ethanolamine. The iron(III) metal centre is six-coordinate by the N and O atoms from the Schiff base ligand, the N atom from a pyridine molecule and two chloride anions in a distorted octahedral geometry. The Fe–O(alkoxo) bond length [Fe1–O1 = 2.105 (2) Å] is longer than the Fe–O(phenoxo) distance [Fe1–O2 = 1.897 (2) Å], which lies well within the range of values reported in the literature (Goodwin et al., 2000; Qian et al., 2008; Hoshino et al., 2009). In the crystal structure, complex molecules and pyridine solvent molecules are linked into a three-dimensional network by O—H···N hydrogen bonds and C—H···π interactions (Table 1).

Experimental

Ethanolamine (1 mmol, 61.08 mg) was dissolved in methanol (10 ml) and added dropwise to a methanol solution of 2-hydroxy-1-naphthaldehyde (1 mmol, 172.19 mg). The mixture was then stirred at 323 K for 2 h. Subsequently, an MeCN/Py solution "(3:1 v/v, 4 ml) of FeCl3.6H2O(1 mmol, 270.29 mg) was added dropwise and stirred for another 7 h. The resulting black solution was filtrated and was allowed to stand at room temperature for about one week, whereupon block crystals suitable for X-ray diffraction analysis were obtained.

Refinement

All H atoms were placed in geometrically idealized positions and treated as riding on their parent atoms, with C—H = 0.93–0.97 Å, O—H = 0.82 Å, and with Uiso(H) = 1.2 Ueq(C) or 1.5 Ueq(O).

Figures

Fig. 1.
The molecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids.

Crystal data

[Fe(C13H12NO2)Cl2(C5H5N)]·C5H5NF(000) = 514
Mr = 499.19Dx = 1.454 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 3504 reflections
a = 7.8590 (6) Åθ = 2.5–28.0°
b = 10.0153 (11) ŵ = 0.92 mm1
c = 14.4884 (16) ÅT = 298 K
β = 90.123 (1)°Block, black
V = 1140.4 (2) Å30.48 × 0.44 × 0.37 mm
Z = 2

Data collection

Bruker SMART 1000 CCD diffractometer3395 independent reflections
Radiation source: fine-focus sealed tube3143 reflections with I > 2σ(I)
graphiteRint = 0.021
phi and ω scansθmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Siemens, 1996)h = −8→9
Tmin = 0.666, Tmax = 0.727k = −11→8
5726 measured reflectionsl = −17→17

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032H-atom parameters constrained
wR(F2) = 0.085w = 1/[σ2(Fo2) + (0.0476P)2 + 0.5289P] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.001
3395 reflectionsΔρmax = 0.25 e Å3
281 parametersΔρmin = −0.19 e Å3
1 restraintAbsolute structure: Flack (1983), 1265 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.02 (2)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Fe10.54656 (5)0.51232 (5)0.28032 (3)0.03179 (13)
Cl10.81839 (12)0.59516 (12)0.27394 (7)0.0505 (3)
Cl20.61339 (13)0.29636 (11)0.33678 (7)0.0486 (3)
N10.2862 (3)0.4752 (3)0.30300 (17)0.0321 (7)
N20.4541 (4)0.7190 (4)0.2447 (2)0.0386 (7)
N30.7698 (4)0.5286 (4)0.52783 (19)0.0458 (8)
O10.5126 (3)0.5757 (3)0.41754 (15)0.0374 (6)
H10.59680.55240.44690.056*
O20.5074 (3)0.4537 (3)0.15755 (16)0.0386 (6)
C10.3621 (4)0.5234 (5)0.4608 (2)0.0434 (9)
H1A0.33300.57570.51490.052*
H1B0.37980.43150.47960.052*
C20.2222 (4)0.5320 (5)0.3892 (2)0.0409 (10)
H2A0.12310.48270.40980.049*
H2B0.18940.62440.37980.049*
C30.1855 (4)0.4104 (4)0.2498 (2)0.0331 (8)
H30.07340.40060.26900.040*
C40.2316 (4)0.3513 (4)0.1627 (2)0.0309 (8)
C50.3927 (4)0.3731 (4)0.1223 (2)0.0334 (8)
C60.4347 (5)0.3075 (5)0.0381 (2)0.0440 (10)
H60.54030.32270.01130.053*
C70.3239 (5)0.2239 (5)−0.0032 (2)0.0505 (11)
H70.35640.1808−0.05720.061*
C80.1613 (5)0.1997 (4)0.0327 (2)0.0419 (10)
C90.1090 (5)0.2669 (4)0.1152 (2)0.0330 (8)
C10−0.0580 (5)0.2445 (4)0.1469 (3)0.0431 (9)
H10−0.09680.29110.19820.052*
C11−0.1640 (6)0.1561 (5)0.1041 (3)0.0566 (12)
H11−0.27330.14260.12680.068*
C12−0.1089 (6)0.0855 (6)0.0261 (3)0.0632 (14)
H12−0.17960.0221−0.00110.076*
C130.0459 (6)0.1095 (5)−0.0094 (3)0.0576 (12)
H130.07830.0656−0.06310.069*
C140.3280 (5)0.7367 (5)0.1839 (3)0.0496 (10)
H140.27860.66220.15650.060*
C150.2690 (7)0.8615 (6)0.1604 (3)0.0659 (14)
H150.18140.87080.11770.079*
C160.3409 (7)0.9727 (5)0.2009 (4)0.0731 (16)
H160.30431.05800.18510.088*
C170.4661 (7)0.9548 (5)0.2644 (4)0.0635 (13)
H170.51471.02790.29400.076*
C180.5204 (5)0.8271 (5)0.2843 (3)0.0509 (10)
H180.60710.81600.32740.061*
C190.8321 (6)0.4104 (5)0.5477 (3)0.0588 (13)
H190.78210.33550.52110.071*
C200.9701 (7)0.3926 (6)0.6070 (4)0.0650 (14)
H201.01130.30770.62000.078*
C211.0421 (5)0.5014 (8)0.6448 (3)0.0656 (14)
H211.13340.49290.68520.079*
C220.9803 (7)0.6227 (7)0.6233 (4)0.0805 (19)
H221.03060.69910.64760.097*
C230.8438 (7)0.6334 (6)0.5658 (4)0.0663 (14)
H230.80090.71780.55270.080*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Fe10.0295 (2)0.0306 (3)0.0353 (2)0.0020 (2)−0.00537 (16)−0.0014 (2)
Cl10.0305 (4)0.0524 (7)0.0685 (6)−0.0014 (4)−0.0044 (4)−0.0056 (5)
Cl20.0574 (6)0.0332 (5)0.0551 (6)0.0102 (5)−0.0071 (4)0.0020 (4)
N10.0296 (14)0.038 (2)0.0290 (13)0.0046 (12)−0.0029 (11)−0.0044 (12)
N20.0401 (17)0.034 (2)0.0420 (16)0.0029 (15)−0.0066 (13)0.0025 (15)
N30.0476 (17)0.046 (2)0.0432 (16)−0.0030 (18)−0.0118 (13)0.0028 (18)
O10.0377 (13)0.0390 (16)0.0354 (12)0.0012 (11)−0.0105 (10)−0.0038 (11)
O20.0354 (13)0.0449 (17)0.0355 (12)−0.0024 (11)−0.0012 (10)−0.0040 (11)
C10.0451 (18)0.053 (3)0.0323 (16)0.001 (2)0.0004 (13)−0.005 (2)
C20.0336 (17)0.051 (3)0.0381 (17)0.0047 (18)−0.0013 (13)−0.0170 (19)
C30.0307 (17)0.032 (2)0.0366 (18)0.0043 (16)−0.0019 (14)0.0004 (16)
C40.0349 (18)0.028 (2)0.0294 (16)0.0088 (15)−0.0046 (14)0.0009 (14)
C50.0358 (18)0.033 (2)0.0313 (17)0.0065 (16)−0.0076 (14)0.0028 (15)
C60.0405 (19)0.060 (3)0.0319 (18)0.006 (2)0.0015 (15)−0.0043 (19)
C70.060 (2)0.060 (3)0.0319 (19)0.011 (2)−0.0023 (17)−0.014 (2)
C80.050 (2)0.042 (3)0.0339 (18)0.002 (2)−0.0114 (16)−0.0019 (17)
C90.0387 (18)0.029 (2)0.0310 (16)0.0043 (15)−0.0086 (14)−0.0003 (14)
C100.040 (2)0.047 (3)0.042 (2)−0.0033 (18)−0.0111 (16)−0.0038 (18)
C110.049 (2)0.066 (3)0.056 (2)−0.011 (2)−0.016 (2)0.001 (2)
C120.071 (3)0.064 (3)0.055 (3)−0.020 (3)−0.026 (2)−0.010 (2)
C130.074 (3)0.054 (3)0.044 (2)−0.002 (2)−0.019 (2)−0.018 (2)
C140.053 (2)0.046 (3)0.049 (2)0.010 (2)−0.0076 (19)0.007 (2)
C150.070 (3)0.069 (4)0.058 (3)0.027 (3)−0.006 (2)0.012 (3)
C160.094 (4)0.047 (4)0.078 (3)0.028 (3)0.015 (3)0.021 (3)
C170.076 (3)0.029 (2)0.085 (3)0.000 (2)0.011 (3)0.000 (2)
C180.051 (2)0.037 (3)0.065 (3)−0.001 (2)−0.0052 (19)−0.001 (2)
C190.060 (3)0.049 (3)0.067 (3)−0.008 (2)−0.017 (2)0.001 (2)
C200.063 (3)0.058 (4)0.074 (3)0.005 (3)−0.011 (2)0.018 (3)
C210.042 (2)0.099 (5)0.056 (2)0.012 (3)−0.0130 (17)−0.011 (3)
C220.061 (3)0.091 (5)0.089 (4)−0.002 (3)−0.021 (3)−0.036 (4)
C230.066 (3)0.049 (3)0.084 (3)0.009 (3)−0.018 (3)−0.012 (3)

Geometric parameters (Å, °)

Fe1—O21.897 (2)C8—C131.417 (6)
Fe1—O12.105 (2)C8—C91.433 (5)
Fe1—N12.106 (3)C9—C101.409 (5)
Fe1—N22.254 (3)C10—C111.364 (6)
Fe1—Cl12.2938 (10)C10—H100.9300
Fe1—Cl22.3709 (12)C11—C121.403 (7)
N1—C31.280 (4)C11—H110.9300
N1—C21.462 (4)C12—C131.344 (7)
N2—C181.331 (6)C12—H120.9300
N2—C141.336 (5)C13—H130.9300
N3—C191.312 (7)C14—C151.375 (7)
N3—C231.319 (6)C14—H140.9300
O1—C11.439 (4)C15—C161.379 (8)
O1—H10.8200C15—H150.9300
O2—C51.313 (4)C16—C171.357 (7)
C1—C21.513 (4)C16—H160.9300
C1—H1A0.9700C17—C181.379 (6)
C1—H1B0.9700C17—H170.9300
C2—H2A0.9700C18—H180.9300
C2—H2B0.9700C19—C201.393 (7)
C3—C41.440 (5)C19—H190.9300
C3—H30.9300C20—C211.344 (9)
C4—C51.414 (5)C20—H200.9300
C4—C91.455 (5)C21—C221.345 (9)
C5—C61.424 (5)C21—H210.9300
C6—C71.348 (6)C22—C231.361 (8)
C6—H60.9300C22—H220.9300
C7—C81.402 (6)C23—H230.9300
C7—H70.9300
O2—Fe1—O1163.37 (10)C6—C7—H7119.0
O2—Fe1—N186.33 (10)C8—C7—H7119.0
O1—Fe1—N177.32 (9)C7—C8—C13122.2 (4)
O2—Fe1—N291.01 (11)C7—C8—C9119.5 (3)
O1—Fe1—N284.14 (11)C13—C8—C9118.3 (4)
N1—Fe1—N283.39 (11)C10—C9—C8117.8 (3)
O2—Fe1—Cl1102.90 (8)C10—C9—C4123.7 (3)
O1—Fe1—Cl192.81 (7)C8—C9—C4118.5 (3)
N1—Fe1—Cl1167.24 (9)C11—C10—C9121.6 (4)
N2—Fe1—Cl187.61 (8)C11—C10—H10119.2
O2—Fe1—Cl294.40 (9)C9—C10—H10119.2
O1—Fe1—Cl288.73 (8)C10—C11—C12120.3 (4)
N1—Fe1—Cl290.00 (9)C10—C11—H11119.9
N2—Fe1—Cl2171.18 (9)C12—C11—H11119.9
Cl1—Fe1—Cl297.95 (4)C13—C12—C11119.9 (4)
C3—N1—C2119.9 (3)C13—C12—H12120.0
C3—N1—Fe1126.5 (2)C11—C12—H12120.0
C2—N1—Fe1113.6 (2)C12—C13—C8121.9 (4)
C18—N2—C14117.8 (4)C12—C13—H13119.0
C18—N2—Fe1121.5 (3)C8—C13—H13119.0
C14—N2—Fe1120.7 (3)N2—C14—C15122.2 (5)
C19—N3—C23117.5 (3)N2—C14—H14118.9
C1—O1—Fe1114.1 (2)C15—C14—H14118.9
C1—O1—H1109.5C14—C15—C16119.4 (4)
Fe1—O1—H1107.4C14—C15—H15120.3
C5—O2—Fe1131.7 (2)C16—C15—H15120.3
O1—C1—C2106.1 (3)C17—C16—C15118.5 (5)
O1—C1—H1A110.5C17—C16—H16120.7
C2—C1—H1A110.5C15—C16—H16120.7
O1—C1—H1B110.5C16—C17—C18119.2 (5)
C2—C1—H1B110.5C16—C17—H17120.4
H1A—C1—H1B108.7C18—C17—H17120.4
N1—C2—C1108.3 (3)N2—C18—C17122.9 (4)
N1—C2—H2A110.0N2—C18—H18118.6
C1—C2—H2A110.0C17—C18—H18118.6
N1—C2—H2B110.0N3—C19—C20122.7 (5)
C1—C2—H2B110.0N3—C19—H19118.7
H2A—C2—H2B108.4C20—C19—H19118.7
N1—C3—C4125.4 (3)C21—C20—C19118.3 (5)
N1—C3—H3117.3C21—C20—H20120.8
C4—C3—H3117.3C19—C20—H20120.8
C5—C4—C3121.8 (3)C20—C21—C22119.1 (4)
C5—C4—C9119.1 (3)C20—C21—H21120.5
C3—C4—C9119.1 (3)C22—C21—H21120.5
O2—C5—C4123.2 (3)C21—C22—C23119.8 (6)
O2—C5—C6117.2 (3)C21—C22—H22120.1
C4—C5—C6119.6 (3)C23—C22—H22120.1
C7—C6—C5121.1 (4)N3—C23—C22122.6 (5)
C7—C6—H6119.5N3—C23—H23118.7
C5—C6—H6119.5C22—C23—H23118.7
C6—C7—C8122.1 (4)
O2—Fe1—N1—C312.9 (3)C3—C4—C5—O2−4.1 (5)
O1—Fe1—N1—C3−170.2 (3)C9—C4—C5—O2176.0 (3)
N2—Fe1—N1—C3104.4 (3)C3—C4—C5—C6177.2 (3)
Cl1—Fe1—N1—C3149.8 (3)C9—C4—C5—C6−2.8 (5)
Cl2—Fe1—N1—C3−81.5 (3)O2—C5—C6—C7−179.5 (4)
O2—Fe1—N1—C2−167.0 (3)C4—C5—C6—C7−0.7 (6)
O1—Fe1—N1—C29.8 (2)C5—C6—C7—C81.7 (7)
N2—Fe1—N1—C2−75.6 (3)C6—C7—C8—C13−178.5 (4)
Cl1—Fe1—N1—C2−30.2 (5)C6—C7—C8—C90.8 (7)
Cl2—Fe1—N1—C298.5 (3)C7—C8—C9—C10177.3 (4)
O2—Fe1—N2—C18−146.3 (3)C13—C8—C9—C10−3.4 (5)
O1—Fe1—N2—C1849.6 (3)C7—C8—C9—C4−4.2 (5)
N1—Fe1—N2—C18127.5 (3)C13—C8—C9—C4175.1 (4)
Cl1—Fe1—N2—C18−43.5 (3)C5—C4—C9—C10−176.5 (3)
O2—Fe1—N2—C1434.9 (3)C3—C4—C9—C103.6 (5)
O1—Fe1—N2—C14−129.1 (3)C5—C4—C9—C85.1 (5)
N1—Fe1—N2—C14−51.3 (3)C3—C4—C9—C8−174.8 (3)
Cl1—Fe1—N2—C14137.8 (3)C8—C9—C10—C113.8 (6)
O2—Fe1—O1—C129.9 (5)C4—C9—C10—C11−174.6 (4)
N1—Fe1—O1—C119.0 (3)C9—C10—C11—C12−0.6 (7)
N2—Fe1—O1—C1103.5 (3)C10—C11—C12—C13−3.2 (8)
Cl1—Fe1—O1—C1−169.2 (3)C11—C12—C13—C83.5 (8)
Cl2—Fe1—O1—C1−71.3 (3)C7—C8—C13—C12179.1 (5)
O1—Fe1—O2—C5−36.4 (6)C9—C8—C13—C12−0.2 (7)
N1—Fe1—O2—C5−25.7 (3)C18—N2—C14—C151.4 (6)
N2—Fe1—O2—C5−109.0 (3)Fe1—N2—C14—C15−179.8 (3)
Cl1—Fe1—O2—C5163.2 (3)N2—C14—C15—C16−0.3 (7)
Cl2—Fe1—O2—C564.0 (3)C14—C15—C16—C17−1.3 (8)
Fe1—O1—C1—C2−42.2 (4)C15—C16—C17—C181.8 (8)
C3—N1—C2—C1145.1 (4)C14—N2—C18—C17−0.9 (6)
Fe1—N1—C2—C1−34.9 (4)Fe1—N2—C18—C17−179.7 (3)
O1—C1—C2—N148.7 (5)C16—C17—C18—N2−0.7 (7)
C2—N1—C3—C4179.1 (4)C23—N3—C19—C200.5 (7)
Fe1—N1—C3—C4−0.9 (5)N3—C19—C20—C21−0.3 (8)
N1—C3—C4—C5−7.3 (6)C19—C20—C21—C22−0.8 (7)
N1—C3—C4—C9172.6 (4)C20—C21—C22—C231.7 (8)
Fe1—O2—C5—C425.9 (5)C19—N3—C23—C220.3 (8)
Fe1—O2—C5—C6−155.4 (3)C21—C22—C23—N3−1.5 (10)

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C4–C9 ring.
D—H···AD—HH···AD···AD—H···A
O1—H1···N30.821.812.617 (4)168
C12—H12···Cgi0.932.713.594 (5)159
C16—H16···Cgii0.932.783.653 (6)157

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2519).

References

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