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Acta Crystallogr Sect E Struct Rep Online. 2008 June 1; 64(Pt 6): m823.
Published online 2008 May 17. doi:  10.1107/S1600536808014074
PMCID: PMC2961544

Tris[2-(propyl­imino­meth­yl)phenolato-κ2 N,O]cobalt(III)

Abstract

The title compound, [Co(C10H12NO)3], was synthesized from cobalt(III) fluoride and 2-(propyl­imino­meth­yl)phenol in refluxing methanol. The CoIII ion is hexa­coordinated by three N and three O atoms from three bidentate Schiff base ligands in an octa­hedral geometry.

Related literature

For related literature, see: Chung et al. (1971 [triangle]); Church & Halvorson (1959 [triangle]); Okabe & Oya (2000 [triangle]); Serre et al. (2005 [triangle]); Pocker & Fong (1980 [triangle]); Scapin et al. (1997 [triangle]).

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Object name is e-64-0m823-scheme1.jpg

Experimental

Crystal data

  • [Co(C10H12NO)3]
  • M r = 545.55
  • Tetragonal, An external file that holds a picture, illustration, etc.
Object name is e-64-0m823-efi1.jpg
  • a = 19.588 (3) Å
  • c = 29.877 (6) Å
  • V = 11464 (3) Å3
  • Z = 16
  • Mo Kα radiation
  • μ = 0.63 mm−1
  • T = 293 (2) K
  • 0.43 × 0.28 × 0.22 mm

Data collection

  • Bruker APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2001 [triangle]) T min = 0.773, T max = 0.873
  • 41404 measured reflections
  • 5133 independent reflections
  • 3104 reflections with I > 2σ(I)
  • R int = 0.075

Refinement

  • R[F 2 > 2σ(F 2)] = 0.047
  • wR(F 2) = 0.092
  • S = 1.00
  • 5133 reflections
  • 337 parameters
  • H-atom parameters constrained
  • Δρmax = 0.29 e Å−3
  • Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: SAINT-Plus (Bruker, 2001 [triangle]); data reduction: SAINT-Plus; 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.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808014074/cf2198sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808014074/cf2198Isup2.hkl

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

Acknowledgments

The authors are grateful for financial support from the Scientific Research Foundation of Outstanding Talented Persons of Henan Province (grant No. 74200510014).

supplementary crystallographic information

Comment

In recent years, Schiff base ligands have been widely used as polydentate ligands, which can coordinate to transition or rare earth ions yielding complexes with interesting properties that are useful in materials science (Church & Halvorson, 1959) and in biological systems (Okabe & Oya, 2000; Serre et al., 2005; Pocker & Fong, 1980; Scapin et al., 1997). Here we report the synthesis and X-ray crystal structure analysis of the title compound, tris(N-n-propylsalicylaldiminato)cobalt(III).

The molecular structure of the title compound is shown in Fig.1. The CoIII ion is hexacoordinated by three N and three O atoms from three bidentate Schiff base ligands, in an octahedral geometry. The Co—N and Co—O bond lengths are in the ranges 1.941 (2)–1.955 (2) and 1.8681 (19)–1.8999 (19) Å, respectively.

Experimental

A mixture of cobalt(III) fluoride (0.5 mmol) and N-n-propylsalicylaldimine (0.5 mmol) in 40 ml methanol solution was refluxed for 5 h. The filtrate from the resulting soution was allowed to evaporate at room temperature for three days. Red crystals were obtained with a yield of 21%. Anal. Calc. for C30H36CoN3O3: C 65.99, H 6.60, N 7.70%; Found: C 65.91, H 6.53, N 7.64%.

Refinement

All H atoms were placed in calculated positions with C—H = 0.93Å and refined as riding with Uiso(H) = 1.2Ueq(carrier).

Figures

Fig. 1.
The molecular structure of (I), drawn with 30% probability displacement ellipsoids for the non-hydrogen atoms.

Crystal data

[Co(C10H12N1O1)3]Z = 16
Mr = 545.55F000 = 4608
Tetragonal, I41/aDx = 1.264 Mg m3
Hall symbol: -I 4adMo Kα radiation λ = 0.71073 Å
a = 19.588 (3) ÅCell parameters from 5133 reflections
b = 19.588 (3) Åθ = 1.2–25.3º
c = 29.877 (6) ŵ = 0.63 mm1
α = 90ºT = 293 (2) K
β = 90ºBlock, red
γ = 90º0.43 × 0.28 × 0.22 mm
V = 11464 (3) Å3

Data collection

Bruker APEXII CCD diffractometer5133 independent reflections
Radiation source: fine-focus sealed tube3104 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.075
T = 293(2) Kθmax = 25.3º
[var phi] and ω scansθmin = 1.2º
Absorption correction: multi-scan(SADABS; Bruker, 2001)h = −23→22
Tmin = 0.773, Tmax = 0.873k = −23→23
41404 measured reflectionsl = −35→35

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047H-atom parameters constrained
wR(F2) = 0.092  w = 1/[σ2(Fo2) + (0.0331P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
5133 reflectionsΔρmax = 0.29 e Å3
337 parametersΔρmin = −0.22 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

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)

xyzUiso*/Ueq
Co10.226327 (19)0.48151 (2)0.006993 (12)0.05600 (15)
C10.12898 (15)0.41326 (14)0.06122 (9)0.0523 (7)
C20.06948 (15)0.37334 (14)0.06292 (10)0.0618 (8)
H20.05620.34900.03760.074*
C30.03038 (16)0.36939 (16)0.10098 (12)0.0729 (9)
H3−0.00900.34290.10100.087*
C40.04897 (19)0.40445 (17)0.13924 (11)0.0760 (10)
H40.02200.40190.16480.091*
C50.10674 (18)0.44248 (16)0.13916 (9)0.0674 (8)
H50.12000.46480.16520.081*
C60.14739 (15)0.44903 (14)0.10029 (9)0.0547 (7)
C70.20795 (17)0.48916 (16)0.10226 (10)0.0664 (9)
H70.22250.50260.13050.080*
C80.3095 (2)0.5453 (3)0.07921 (14)0.1220 (15)
H8A0.33710.51420.09680.146*
H8B0.33310.55160.05100.146*
C90.3108 (3)0.6025 (3)0.0992 (2)0.1486 (18)
H9A0.28880.59680.12810.235*
H9B0.28320.63430.08210.235*
C100.3811 (2)0.6360 (2)0.10728 (15)0.1317 (16)
H10A0.41460.60110.11240.198*
H10B0.37860.66530.13300.198*
H10C0.39370.66230.08150.198*
C110.34024 (18)0.54969 (19)−0.03344 (10)0.0704 (9)
C120.36719 (19)0.6075 (2)−0.05589 (12)0.0967 (12)
H120.34050.6465−0.05880.116*
C130.4318 (2)0.6068 (3)−0.07339 (13)0.1169 (15)
H130.44820.6453−0.08810.140*
C140.4726 (2)0.5506 (3)−0.06963 (14)0.1170 (16)
H140.51620.5507−0.08190.140*
C150.44864 (19)0.4935 (3)−0.04758 (13)0.1026 (13)
H150.47670.4554−0.04480.123*
C160.38243 (17)0.4920 (2)−0.02915 (11)0.0738 (9)
C170.36155 (18)0.43177 (19)−0.00564 (10)0.0754 (10)
H170.39440.3979−0.00250.090*
C180.29465 (17)0.35230 (18)0.03437 (11)0.0838 (10)
H18A0.26670.35850.06090.101*
H18B0.33910.33610.04400.101*
C190.2619 (2)0.29876 (19)0.00453 (14)0.1015 (12)
H19A0.25420.25800.02220.122*
H19B0.21760.3156−0.00500.122*
C200.3010 (2)0.2796 (2)−0.03554 (17)0.1486 (18)
H20A0.30960.3195−0.05330.223*
H20B0.27530.2472−0.05280.223*
H20C0.34360.2595−0.02670.223*
C210.15472 (16)0.43302 (15)−0.06742 (9)0.0538 (7)
C220.14576 (18)0.37797 (15)−0.09769 (10)0.0669 (9)
H220.18290.3508−0.10530.080*
C230.0827 (2)0.36426 (17)−0.11598 (10)0.0717 (9)
H230.07810.3272−0.13520.086*
C240.02697 (18)0.40319 (16)−0.10686 (10)0.0719 (9)
H24−0.01490.3937−0.12020.086*
C250.03369 (16)0.45678 (16)−0.07764 (10)0.0674 (9)
H25−0.00410.4838−0.07130.081*
C260.09572 (16)0.47160 (14)−0.05731 (9)0.0554 (7)
C270.09995 (15)0.52896 (15)−0.02763 (10)0.0632 (8)
H270.06360.5595−0.02840.076*
C280.14549 (16)0.60718 (16)0.02585 (11)0.0804 (10)
H28A0.18960.62930.02320.096*
H28B0.13960.59520.05710.096*
C290.09207 (19)0.65893 (16)0.01440 (11)0.0851 (10)
H29A0.04710.63900.01820.102*
H29B0.09700.6726−0.01670.102*
C300.0990 (2)0.72063 (16)0.04423 (12)0.0996 (12)
H30A0.08630.70870.07430.149*
H30B0.06960.75630.03350.149*
H30C0.14550.73620.04390.149*
N10.24463 (13)0.50871 (13)0.06881 (8)0.0667 (7)
N20.30289 (13)0.41897 (13)0.01157 (8)0.0649 (7)
N30.14848 (12)0.54281 (12)−0.00012 (8)0.0595 (6)
O10.16488 (9)0.41360 (9)0.02443 (6)0.0589 (5)
O20.27882 (10)0.55441 (10)−0.01683 (7)0.0712 (6)
O30.21526 (10)0.44676 (10)−0.05193 (6)0.0622 (5)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Co10.0519 (3)0.0672 (3)0.0489 (2)0.0033 (2)−0.00188 (19)0.0004 (2)
C10.058 (2)0.0494 (18)0.0493 (18)0.0086 (15)−0.0039 (15)0.0060 (14)
C20.065 (2)0.060 (2)0.060 (2)0.0047 (17)−0.0069 (17)0.0039 (16)
C30.062 (2)0.076 (2)0.080 (2)−0.0011 (18)0.0054 (19)0.020 (2)
C40.087 (3)0.082 (3)0.059 (2)0.004 (2)0.012 (2)0.0108 (19)
C50.087 (3)0.069 (2)0.0460 (19)0.009 (2)−0.0033 (18)0.0024 (15)
C60.064 (2)0.0570 (19)0.0434 (17)0.0091 (16)−0.0052 (15)0.0019 (14)
C70.077 (2)0.076 (2)0.0454 (18)0.0046 (19)−0.0104 (17)−0.0060 (17)
C80.127 (4)0.149 (4)0.089 (3)−0.038 (3)0.005 (3)−0.034 (3)
C90.145 (4)0.137 (4)0.164 (5)0.003 (3)0.043 (4)−0.037 (3)
C100.123 (4)0.114 (3)0.158 (4)−0.065 (3)−0.028 (3)0.001 (3)
C110.057 (2)0.093 (3)0.061 (2)−0.010 (2)−0.0089 (18)0.0071 (19)
C120.067 (3)0.124 (3)0.099 (3)−0.012 (2)−0.004 (2)0.030 (2)
C130.075 (3)0.169 (5)0.107 (3)−0.030 (3)−0.002 (3)0.050 (3)
C140.065 (3)0.183 (5)0.103 (3)−0.014 (3)0.017 (2)0.025 (3)
C150.060 (3)0.155 (4)0.093 (3)0.005 (3)−0.002 (2)−0.005 (3)
C160.052 (2)0.108 (3)0.062 (2)0.002 (2)−0.0023 (17)−0.001 (2)
C170.064 (2)0.095 (3)0.067 (2)0.021 (2)−0.0136 (19)−0.001 (2)
C180.079 (2)0.090 (3)0.082 (2)0.021 (2)−0.0080 (19)0.019 (2)
C190.107 (3)0.075 (3)0.122 (3)0.013 (2)−0.001 (3)−0.002 (2)
C200.145 (4)0.137 (4)0.164 (5)0.003 (3)0.043 (4)−0.037 (3)
C210.066 (2)0.0570 (19)0.0383 (16)0.0073 (17)−0.0011 (15)0.0092 (14)
C220.089 (3)0.063 (2)0.0491 (18)0.0159 (19)0.0059 (18)0.0077 (16)
C230.103 (3)0.060 (2)0.0524 (19)−0.006 (2)−0.012 (2)−0.0017 (15)
C240.086 (3)0.067 (2)0.063 (2)−0.006 (2)−0.0177 (18)0.0015 (18)
C250.069 (2)0.065 (2)0.069 (2)0.0059 (17)−0.0114 (17)0.0030 (18)
C260.063 (2)0.0517 (18)0.0515 (18)0.0050 (16)−0.0064 (15)0.0026 (15)
C270.057 (2)0.063 (2)0.069 (2)0.0084 (16)−0.0028 (17)−0.0052 (17)
C280.072 (2)0.080 (2)0.090 (2)0.006 (2)−0.0137 (19)−0.023 (2)
C290.102 (3)0.070 (2)0.084 (2)0.005 (2)0.005 (2)−0.0036 (19)
C300.125 (3)0.063 (2)0.110 (3)0.003 (2)0.007 (2)−0.019 (2)
N10.0612 (17)0.0784 (19)0.0604 (17)−0.0057 (14)−0.0059 (14)−0.0099 (14)
N20.0602 (17)0.0818 (19)0.0527 (15)0.0094 (15)−0.0065 (13)0.0049 (14)
N30.0533 (15)0.0673 (17)0.0578 (16)0.0018 (13)−0.0015 (12)−0.0110 (13)
O10.0628 (13)0.0681 (13)0.0459 (11)−0.0031 (10)0.0027 (10)−0.0061 (10)
O20.0530 (13)0.0765 (14)0.0840 (15)0.0001 (11)0.0039 (11)0.0079 (12)
O30.0566 (13)0.0831 (14)0.0468 (12)0.0152 (11)0.0020 (10)0.0057 (10)

Geometric parameters (Å, °)

Co1—O11.8681 (19)C15—C161.409 (4)
Co1—O21.898 (2)C15—H150.930
Co1—O31.8999 (19)C16—C171.432 (4)
Co1—N21.941 (2)C17—N21.283 (4)
Co1—N31.952 (2)C17—H170.930
Co1—N11.955 (2)C18—N21.482 (4)
C1—O11.305 (3)C18—C191.519 (4)
C1—C21.405 (4)C18—H18A0.970
C1—C61.409 (4)C18—H18B0.970
C2—C31.373 (4)C19—C201.470 (5)
C2—H20.930C19—H19A0.970
C3—C41.383 (4)C19—H19B0.970
C3—H30.930C20—H20A0.960
C4—C51.355 (4)C20—H20B0.960
C4—H40.930C20—H20C0.960
C5—C61.414 (4)C21—O31.301 (3)
C5—H50.930C21—C221.418 (4)
C6—C71.424 (4)C21—C261.414 (4)
C7—N11.289 (3)C22—C231.377 (4)
C7—H70.930C22—H220.930
C8—C91.271 (5)C23—C241.359 (4)
C8—N11.492 (4)C23—H230.930
C8—H8A0.970C24—C251.372 (4)
C8—H8B0.970C24—H240.930
C9—C101.544 (6)C25—C261.389 (4)
C9—H9A0.970C25—H250.930
C9—H9B0.970C26—C271.434 (4)
C10—H10A0.960C27—N31.286 (3)
C10—H10B0.960C27—H270.930
C10—H10C0.960C28—N31.482 (3)
C11—O21.305 (3)C28—C291.497 (4)
C11—C121.418 (4)C28—H28A0.970
C11—C161.407 (4)C28—H28B0.970
C12—C131.369 (5)C29—C301.508 (4)
C12—H120.930C29—H29A0.970
C13—C141.366 (5)C29—H29B0.970
C13—H130.930C30—H30A0.960
C14—C151.380 (5)C30—H30B0.960
C14—H140.930C30—H30C0.960
O1—Co1—O2171.62 (8)N2—C17—C16127.8 (3)
O1—Co1—O385.97 (8)N2—C17—H17116.1
O2—Co1—O389.08 (9)C16—C17—H17116.1
O1—Co1—N291.64 (10)N2—C18—C19112.6 (3)
O2—Co1—N294.74 (10)N2—C18—H18A109.1
O3—Co1—N285.83 (9)C19—C18—H18A109.1
O1—Co1—N388.00 (9)N2—C18—H18B109.1
O2—Co1—N385.39 (9)C19—C18—H18B109.1
O3—Co1—N391.74 (9)H18A—C18—H18B107.8
N2—Co1—N3177.56 (10)C20—C19—C18115.7 (3)
O1—Co1—N192.80 (10)C20—C19—H19A108.3
O2—Co1—N192.85 (10)C18—C19—H19A108.3
O3—Co1—N1173.60 (9)C20—C19—H19B108.4
N2—Co1—N187.93 (10)C18—C19—H19B108.4
N3—Co1—N194.50 (10)H19A—C19—H19B107.4
O1—C1—C2118.7 (3)C19—C20—H20A109.5
O1—C1—C6123.9 (3)C19—C20—H20B109.5
C2—C1—C6117.4 (3)H20A—C20—H20B109.5
C3—C2—C1121.6 (3)C19—C20—H20C109.5
C3—C2—H2119.2H20A—C20—H20C109.5
C1—C2—H2119.2H20B—C20—H20C109.5
C4—C3—C2120.7 (3)O3—C21—C22119.8 (3)
C4—C3—H3119.7O3—C21—C26124.0 (3)
C2—C3—H3119.7C22—C21—C26116.2 (3)
C5—C4—C3119.5 (3)C23—C22—C21120.8 (3)
C5—C4—H4120.3C23—C22—H22119.6
C3—C4—H4120.3C21—C22—H22119.6
C4—C5—C6121.5 (3)C24—C23—C22122.1 (3)
C4—C5—H5119.3C24—C23—H23119.0
C6—C5—H5119.3C22—C23—H23118.9
C5—C6—C1119.4 (3)C25—C24—C23118.7 (3)
C5—C6—C7119.0 (3)C25—C24—H24120.7
C1—C6—C7121.5 (3)C23—C24—H24120.7
N1—C7—C6126.6 (3)C24—C25—C26121.5 (3)
N1—C7—H7116.7C24—C25—H25119.3
C6—C7—H7116.7C26—C25—H25119.3
C9—C8—N1122.6 (5)C25—C26—C21120.7 (3)
C9—C8—H8A106.7C25—C26—C27119.0 (3)
N1—C8—H8A106.7C21—C26—C27120.3 (3)
C9—C8—H8B106.7N3—C27—C26127.1 (3)
N1—C8—H8B106.7N3—C27—H27116.4
H8A—C8—H8B106.6C26—C27—H27116.4
C8—C9—C10117.7 (5)N3—C28—C29119.0 (3)
C8—C9—H9A107.9N3—C28—H28A107.6
C10—C9—H9A107.9C29—C28—H28A107.6
C8—C9—H9B107.9N3—C28—H28B107.6
C10—C9—H9B107.9C29—C28—H28B107.6
H9A—C9—H9B107.2H28A—C28—H28B107.0
C9—C10—H10A109.5C28—C29—C30110.2 (3)
C9—C10—H10B109.5C28—C29—H29A109.6
H10A—C10—H10B109.5C30—C29—H29A109.6
C9—C10—H10C109.5C28—C29—H29B109.6
H10A—C10—H10C109.5C30—C29—H29B109.6
H10B—C10—H10C109.5H29A—C29—H29B108.1
O2—C11—C12117.8 (3)C29—C30—H30A109.5
O2—C11—C16124.4 (3)C29—C30—H30B109.5
C12—C11—C16117.8 (3)H30A—C30—H30B109.5
C13—C12—C11121.1 (4)C29—C30—H30C109.5
C13—C12—H12119.4H30A—C30—H30C109.5
C11—C12—H12119.4H30B—C30—H30C109.5
C14—C13—C12121.1 (4)C7—N1—C8117.1 (3)
C14—C13—H13119.4C7—N1—Co1123.3 (2)
C12—C13—H13119.4C8—N1—Co1118.9 (2)
C15—C14—C13119.6 (4)C17—N2—C18117.0 (3)
C15—C14—H14120.2C17—N2—Co1122.7 (2)
C13—C14—H14120.2C18—N2—Co1120.3 (2)
C14—C15—C16121.1 (4)C27—N3—C28119.0 (2)
C14—C15—H15119.4C27—N3—Co1121.2 (2)
C16—C15—H15119.4C28—N3—Co1119.82 (19)
C15—C16—C11119.2 (4)C1—O1—Co1125.85 (17)
C15—C16—C17118.2 (4)C11—O2—Co1126.1 (2)
C11—C16—C17122.6 (3)C21—O3—Co1120.51 (17)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CF2198).

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