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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): m1633.
Published online 2010 November 24. doi:  10.1107/S1600536810047793
PMCID: PMC3011786

Bis(4-chloro­pyridine){2,2′-[ethane-1,2-diylbis(nitrilo­methyl­idyne)]diphenolato}cobalt(III) perchlorate methanol monosolvate

Abstract

In the title complex, [Co(C16H14N2O2)(C5H4ClN)2]ClO4·CH3OH, the CoIII ion is in a slightly distorted octa­hedral CoN4O2 coordination environment with the two 4-chloro­pyridine ligands in a trans arrangement.

Related literature

For related structures, see: Chen (2008 [triangle]); Kitaura et al. (1987 [triangle]); Shi et al. (1995 [triangle]); Zhou (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1633-scheme1.jpg

Experimental

Crystal data

  • [Co(C16H14N2O2)(C5H4ClN)2]ClO4·CH4O
  • M r = 683.80
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1633-efi1.jpg
  • a = 9.0244 (12) Å
  • b = 11.2625 (16) Å
  • c = 15.052 (2) Å
  • α = 92.757 (2)°
  • β = 103.843 (2)°
  • γ = 95.396 (2)°
  • V = 1474.9 (3) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.91 mm−1
  • T = 293 K
  • 0.31 × 0.29 × 0.25 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2008a [triangle]) T min = 0.767, T max = 0.805
  • 7378 measured reflections
  • 5144 independent reflections
  • 4213 reflections with I > 2σ(I)
  • R int = 0.016

Refinement

  • R[F 2 > 2σ(F 2)] = 0.052
  • wR(F 2) = 0.160
  • S = 1.05
  • 5144 reflections
  • 380 parameters
  • H-atom parameters constrained
  • Δρmax = 1.21 e Å−3
  • Δρmin = −0.49 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, 2008b [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008b [triangle]); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810047793/hg2742sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810047793/hg2742Isup2.hkl

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

Acknowledgments

The author thanks the Doctoral Starting Fund of Shandong University of Technology for support.

supplementary crystallographic information

Comment

Tetradentate Schiff-base ligands, due to their excellent chelating ability for metal atoms, have been widely used to synthsize transition metal complexes. Here, we report the crystal structure of a CoIII complex based on tetradentate Schiff base ligand N,N'-bis(salicylidene)-1,2-diphenyl-1,2-ethanediamine.

The cation structure of the title complex is shown in Fig. 1. The CoIII ion is six coordinated by a N4O2 unit, in which the four equational sites are occupied by two N atoms and two O atoms from the tetradentate Schiff base ligand and the two axial sites are occupied by the N atoms of two 4-chloro-pyridine ligands, therefore forming a slightly distorted octahedral coordination environment. The Co—O, Co—NSchiff-base and Co—Npyridinebond lengths are 1.891 (2), 1.898 (2),1.892 (3), 1.897 (3), 1.977 (3) and 1.995 (3)A%, respectively, which are all comparable to the corresponding bond lengths found in the previously reported CoIII Schiff-base complexes (Chen, 2008; Kitaura, et al., 1987; Shi, et al., 1995; Zhou, 2009).

Experimental

The synthesis of the title complex was carried out by mixing Co(ClO4)2.6H2O (0.1 mmol, 36.6 mg), 4-chloro-pyridine (0.2 mm mol, 22.8 mg) and the Schiff-base ligand (0.1 mmol, 26.8 mg) in methanol. After the mixture was stirred for about half an hour at room temperature in air, it was filtered, and the filtrate was allowed to partially evaporate for one week to produce crystals suitable for X-ray diffraction with an yield about 51%. Anal. Calcd for C27H26Cl3CoN4O7: C, 47.42; H, 3.83; N, 8.19. Found: C, 47.54; H, 3.75; N, 8.095. Main IR bands (cm-1): 3020 (s, C—H),1618 (m, C=N), 1093 (s, Cl=O).

Refinement

All the H atoms bonded to the C atoms were placed using the HFIX commands in SHELXL-97 with C—H distances of 0.93 and 0.96 Å, and were allowed for as riding atoms with Uiso(H) = 1.2Ueq(C) or Uiso(H) = 1.5Ueq(C), respectively. For the H atoms bonded to O atom, it was found from difference Fourier maps with the bond lengths restrained to 0.82 Å, and was allowed for as riding atoms with Uiso(H) = 1.5Ueq(O).

Figures

Fig. 1.
The cation of the title complex with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. All the H atoms, the balanced ClO4- anion and the solvent methanol are not shown.

Crystal data

[Co(C16H14N2O2)(C5H4ClN)2]ClO4·CH4OZ = 2
Mr = 683.80F(000) = 700
Triclinic, P1Dx = 1.540 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.0244 (12) ÅCell parameters from 1564 reflections
b = 11.2625 (16) Åθ = 2.7–27.9°
c = 15.052 (2) ŵ = 0.91 mm1
α = 92.757 (2)°T = 293 K
β = 103.843 (2)°Block, red-brown
γ = 95.396 (2)°0.31 × 0.29 × 0.25 mm
V = 1474.9 (3) Å3

Data collection

Bruker APEXII CCD area-detector diffractometer5144 independent reflections
Radiation source: fine-focus sealed tube4213 reflections with I > 2σ(I)
graphiteRint = 0.016
[var phi] and ω scansθmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)h = −10→10
Tmin = 0.767, Tmax = 0.805k = −12→13
7378 measured reflectionsl = −12→17

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.160H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0871P)2 + 1.6441P] where P = (Fo2 + 2Fc2)/3
5144 reflections(Δ/σ)max < 0.001
380 parametersΔρmax = 1.21 e Å3
0 restraintsΔρmin = −0.49 e Å3

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
Co10.86908 (5)0.11688 (4)0.27546 (3)0.03389 (18)
Cl10.7528 (2)−0.42638 (12)0.38879 (11)0.0922 (5)
Cl21.12614 (17)0.66668 (11)0.25101 (11)0.0786 (4)
Cl30.18397 (16)0.27636 (12)0.02468 (9)0.0665 (3)
O11.0710 (3)0.1026 (2)0.34504 (16)0.0395 (6)
O20.8300 (3)0.1686 (2)0.38825 (16)0.0390 (6)
O30.0318 (7)0.2275 (8)−0.0063 (5)0.186 (3)
O40.2366 (8)0.3413 (8)−0.0360 (5)0.178 (3)
O50.2650 (11)0.1777 (7)0.0309 (7)0.222 (4)
O60.2264 (10)0.3178 (9)0.1133 (4)0.205 (4)
O70.5606 (10)0.2638 (9)0.9505 (7)0.221 (5)
H70.54170.27681.00050.332*
N10.9058 (4)0.0653 (3)0.1619 (2)0.0401 (7)
N20.6671 (3)0.1307 (3)0.2060 (2)0.0374 (7)
N30.8215 (3)−0.0521 (3)0.3026 (2)0.0384 (7)
N40.9340 (3)0.2864 (3)0.2621 (2)0.0390 (7)
C11.1544 (4)−0.0002 (3)0.2244 (3)0.0397 (8)
C21.1695 (4)0.0401 (3)0.3167 (2)0.0357 (8)
C31.2979 (4)0.0125 (4)0.3825 (3)0.0471 (9)
H31.30990.03750.44380.056*
C41.4067 (5)−0.0514 (4)0.3574 (3)0.0563 (11)
H41.4909−0.06870.40220.068*
C51.3924 (5)−0.0902 (4)0.2664 (3)0.0554 (11)
H51.4667−0.13270.25020.066*
C61.2690 (5)−0.0655 (4)0.2015 (3)0.0511 (10)
H61.2590−0.09180.14070.061*
C71.0261 (5)0.0194 (4)0.1520 (3)0.0448 (9)
H7A1.0303−0.00310.09240.054*
C80.5817 (4)0.2362 (3)0.3251 (3)0.0392 (8)
C90.7113 (4)0.2225 (3)0.3977 (2)0.0358 (8)
C100.7089 (5)0.2673 (4)0.4864 (3)0.0456 (9)
H100.79150.25890.53540.055*
C110.5884 (5)0.3226 (4)0.5022 (3)0.0516 (10)
H110.59000.35040.56160.062*
C120.4637 (5)0.3381 (4)0.4310 (3)0.0577 (11)
H120.38310.37730.44230.069*
C130.4607 (5)0.2947 (4)0.3435 (3)0.0509 (10)
H130.37680.30430.29570.061*
C140.5654 (4)0.1835 (3)0.2337 (3)0.0413 (9)
H140.47290.18840.19120.050*
C150.7786 (5)0.0764 (4)0.0805 (3)0.0520 (11)
H15A0.77190.01100.03480.062*
H15B0.79670.15110.05330.062*
C160.6310 (5)0.0731 (4)0.1120 (3)0.0495 (10)
H16A0.55710.11530.07110.059*
H16B0.5870−0.00900.11140.059*
C170.7805 (5)−0.1467 (4)0.2413 (3)0.0454 (9)
H170.7667−0.13330.17950.055*
C180.7576 (5)−0.2624 (4)0.2642 (3)0.0541 (11)
H180.7278−0.32530.21920.065*
C190.7798 (5)−0.2828 (4)0.3555 (3)0.0534 (11)
C200.8241 (6)−0.1875 (4)0.4200 (3)0.0570 (11)
H200.8399−0.19920.48220.068*
C210.8445 (5)−0.0751 (4)0.3914 (3)0.0470 (9)
H210.8760−0.01130.43560.056*
C220.8877 (5)0.3475 (4)0.1886 (3)0.0533 (11)
H220.81440.30900.13880.064*
C230.9419 (6)0.4633 (4)0.1823 (3)0.0620 (12)
H230.90670.50220.12940.074*
C241.0492 (5)0.5210 (4)0.2553 (3)0.0522 (10)
C251.0946 (5)0.4621 (4)0.3331 (3)0.0609 (12)
H251.16420.50030.38460.073*
C261.0355 (5)0.3463 (4)0.3333 (3)0.0548 (11)
H261.06760.30660.38620.066*
C270.6289 (12)0.3621 (9)0.9273 (7)0.150 (4)
H27A0.61900.42890.96660.225*
H27B0.58190.37520.86470.225*
H27C0.73570.35370.93350.225*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Co10.0333 (3)0.0412 (3)0.0266 (3)0.0087 (2)0.00415 (19)0.0042 (2)
Cl10.1540 (16)0.0488 (7)0.0981 (11)0.0199 (8)0.0718 (11)0.0204 (7)
Cl20.0851 (9)0.0531 (7)0.0944 (10)−0.0081 (6)0.0192 (8)0.0193 (7)
Cl30.0745 (8)0.0669 (8)0.0580 (7)0.0084 (6)0.0148 (6)0.0113 (6)
O10.0356 (13)0.0489 (15)0.0327 (13)0.0113 (11)0.0038 (10)0.0019 (11)
O20.0367 (13)0.0500 (15)0.0303 (13)0.0143 (11)0.0048 (10)0.0017 (11)
O30.092 (4)0.272 (9)0.165 (6)−0.034 (5)−0.003 (4)0.019 (6)
O40.154 (6)0.236 (8)0.141 (5)−0.011 (5)0.026 (4)0.103 (5)
O50.214 (8)0.129 (6)0.277 (10)0.069 (6)−0.044 (7)−0.029 (6)
O60.208 (8)0.300 (11)0.093 (4)0.056 (7)0.013 (5)−0.048 (5)
O70.202 (8)0.219 (9)0.301 (12)0.090 (7)0.123 (8)0.146 (9)
N10.0430 (17)0.0515 (19)0.0262 (15)0.0089 (15)0.0073 (13)0.0070 (13)
N20.0361 (16)0.0439 (17)0.0302 (15)0.0077 (13)0.0028 (12)0.0022 (13)
N30.0360 (16)0.0485 (18)0.0307 (16)0.0098 (14)0.0061 (13)0.0040 (14)
N40.0352 (16)0.0464 (18)0.0351 (16)0.0082 (13)0.0062 (13)0.0068 (14)
C10.041 (2)0.042 (2)0.041 (2)0.0057 (16)0.0176 (17)0.0097 (16)
C20.0358 (19)0.0339 (18)0.0392 (19)0.0043 (15)0.0116 (15)0.0068 (15)
C30.039 (2)0.056 (2)0.047 (2)0.0102 (18)0.0079 (17)0.0071 (19)
C40.036 (2)0.066 (3)0.068 (3)0.017 (2)0.009 (2)0.013 (2)
C50.041 (2)0.055 (3)0.079 (3)0.0165 (19)0.027 (2)0.014 (2)
C60.054 (2)0.054 (2)0.054 (2)0.011 (2)0.028 (2)0.009 (2)
C70.053 (2)0.053 (2)0.0327 (19)0.0087 (19)0.0177 (17)0.0069 (17)
C80.0362 (19)0.038 (2)0.044 (2)0.0060 (15)0.0088 (16)0.0048 (16)
C90.0383 (19)0.0320 (18)0.0374 (19)0.0025 (15)0.0101 (15)0.0024 (15)
C100.048 (2)0.048 (2)0.041 (2)0.0070 (18)0.0107 (18)−0.0025 (17)
C110.055 (2)0.053 (2)0.050 (2)0.006 (2)0.020 (2)−0.0059 (19)
C120.048 (2)0.060 (3)0.071 (3)0.016 (2)0.023 (2)−0.005 (2)
C130.041 (2)0.053 (2)0.057 (3)0.0109 (19)0.0073 (19)0.001 (2)
C140.0317 (18)0.046 (2)0.042 (2)0.0060 (16)0.0003 (16)0.0062 (17)
C150.055 (2)0.073 (3)0.0266 (19)0.019 (2)0.0024 (17)0.0043 (19)
C160.048 (2)0.062 (3)0.033 (2)0.0135 (19)−0.0048 (17)−0.0018 (18)
C170.050 (2)0.049 (2)0.038 (2)0.0106 (18)0.0089 (17)0.0044 (18)
C180.064 (3)0.047 (2)0.054 (3)0.009 (2)0.018 (2)−0.002 (2)
C190.065 (3)0.041 (2)0.066 (3)0.016 (2)0.032 (2)0.012 (2)
C200.077 (3)0.057 (3)0.043 (2)0.018 (2)0.021 (2)0.014 (2)
C210.057 (2)0.048 (2)0.036 (2)0.0127 (19)0.0097 (18)0.0051 (17)
C220.064 (3)0.052 (2)0.040 (2)0.003 (2)0.0029 (19)0.0099 (19)
C230.079 (3)0.061 (3)0.046 (3)0.008 (2)0.012 (2)0.019 (2)
C240.045 (2)0.048 (2)0.066 (3)0.0067 (19)0.017 (2)0.013 (2)
C250.053 (3)0.050 (3)0.067 (3)−0.001 (2)−0.009 (2)0.007 (2)
C260.053 (2)0.053 (3)0.048 (2)0.006 (2)−0.008 (2)0.011 (2)
C270.172 (10)0.128 (7)0.158 (9)−0.036 (7)0.078 (8)−0.001 (7)

Geometric parameters (Å, °)

Co1—O21.891 (2)C8—C131.402 (5)
Co1—N11.892 (3)C8—C91.423 (5)
Co1—N21.897 (3)C8—C141.440 (5)
Co1—O11.898 (2)C9—C101.410 (5)
Co1—N41.977 (3)C10—C111.365 (6)
Co1—N31.995 (3)C10—H100.9300
Cl1—C191.728 (4)C11—C121.387 (6)
Cl2—C241.730 (4)C11—H110.9300
Cl3—O41.342 (6)C12—C131.376 (6)
Cl3—O61.344 (6)C12—H120.9300
Cl3—O51.382 (7)C13—H130.9300
Cl3—O31.391 (6)C14—H140.9300
O1—C21.318 (4)C15—C161.515 (6)
O2—C91.312 (4)C15—H15A0.9700
O7—C271.319 (10)C15—H15B0.9700
O7—H70.8200C16—H16A0.9700
N1—C71.282 (5)C16—H16B0.9700
N1—C151.485 (5)C17—C181.373 (6)
N2—C141.278 (5)C17—H170.9300
N2—C161.477 (5)C18—C191.374 (6)
N3—C171.339 (5)C18—H180.9300
N3—C211.344 (5)C19—C201.375 (6)
N4—C221.334 (5)C20—C211.366 (6)
N4—C261.337 (5)C20—H200.9300
C1—C21.412 (5)C21—H210.9300
C1—C61.420 (5)C22—C231.365 (6)
C1—C71.430 (5)C22—H220.9300
C2—C31.403 (5)C23—C241.369 (6)
C3—C41.381 (6)C23—H230.9300
C3—H30.9300C24—C251.369 (6)
C4—C51.390 (7)C25—C261.363 (6)
C4—H40.9300C25—H250.9300
C5—C61.355 (6)C26—H260.9300
C5—H50.9300C27—H27A0.9600
C6—H60.9300C27—H27B0.9600
C7—H7A0.9300C27—H27C0.9600
O2—Co1—N1179.33 (12)C11—C10—C9121.7 (4)
O2—Co1—N294.28 (12)C11—C10—H10119.2
N1—Co1—N285.06 (13)C9—C10—H10119.2
O2—Co1—O185.71 (10)C10—C11—C12121.1 (4)
N1—Co1—O194.95 (12)C10—C11—H11119.5
N2—Co1—O1179.83 (13)C12—C11—H11119.5
O2—Co1—N487.07 (12)C13—C12—C11119.2 (4)
N1—Co1—N492.94 (13)C13—C12—H12120.4
N2—Co1—N491.30 (13)C11—C12—H12120.4
O1—Co1—N488.86 (12)C12—C13—C8121.3 (4)
O2—Co1—N389.24 (12)C12—C13—H13119.4
N1—Co1—N390.81 (13)C8—C13—H13119.4
N2—Co1—N394.37 (13)N2—C14—C8125.6 (3)
O1—Co1—N385.46 (12)N2—C14—H14117.2
N4—Co1—N3173.45 (12)C8—C14—H14117.2
O4—Cl3—O6117.6 (6)N1—C15—C16107.9 (3)
O4—Cl3—O5104.2 (7)N1—C15—H15A110.1
O6—Cl3—O598.6 (6)C16—C15—H15A110.1
O4—Cl3—O3114.2 (5)N1—C15—H15B110.1
O6—Cl3—O3115.2 (5)C16—C15—H15B110.1
O5—Cl3—O3103.6 (6)H15A—C15—H15B108.4
C2—O1—Co1124.5 (2)N2—C16—C15108.2 (3)
C9—O2—Co1125.6 (2)N2—C16—H16A110.1
C27—O7—H7109.5C15—C16—H16A110.1
C7—N1—C15119.9 (3)N2—C16—H16B110.1
C7—N1—Co1125.3 (3)C15—C16—H16B110.1
C15—N1—Co1114.8 (2)H16A—C16—H16B108.4
C14—N2—C16119.9 (3)N3—C17—C18123.9 (4)
C14—N2—Co1126.0 (3)N3—C17—H17118.1
C16—N2—Co1114.1 (2)C18—C17—H17118.1
C17—N3—C21116.5 (3)C17—C18—C19118.3 (4)
C17—N3—Co1126.2 (3)C17—C18—H18120.8
C21—N3—Co1117.1 (3)C19—C18—H18120.8
C22—N4—C26116.2 (4)C18—C19—C20119.0 (4)
C22—N4—Co1126.6 (3)C18—C19—Cl1120.5 (4)
C26—N4—Co1117.2 (3)C20—C19—Cl1120.4 (4)
C2—C1—C6119.3 (4)C21—C20—C19119.0 (4)
C2—C1—C7122.9 (3)C21—C20—H20120.5
C6—C1—C7117.8 (4)C19—C20—H20120.5
O1—C2—C3117.9 (3)N3—C21—C20123.3 (4)
O1—C2—C1124.1 (3)N3—C21—H21118.3
C3—C2—C1118.0 (3)C20—C21—H21118.3
C4—C3—C2120.9 (4)N4—C22—C23123.7 (4)
C4—C3—H3119.5N4—C22—H22118.1
C2—C3—H3119.5C23—C22—H22118.1
C3—C4—C5121.1 (4)C22—C23—C24118.7 (4)
C3—C4—H4119.5C22—C23—H23120.7
C5—C4—H4119.5C24—C23—H23120.7
C6—C5—C4119.2 (4)C23—C24—C25119.0 (4)
C6—C5—H5120.4C23—C24—Cl2121.1 (3)
C4—C5—H5120.4C25—C24—Cl2119.9 (4)
C5—C6—C1121.5 (4)C26—C25—C24118.5 (4)
C5—C6—H6119.3C26—C25—H25120.7
C1—C6—H6119.3C24—C25—H25120.7
N1—C7—C1125.7 (3)N4—C26—C25123.9 (4)
N1—C7—H7A117.2N4—C26—H26118.1
C1—C7—H7A117.2C25—C26—H26118.1
C13—C8—C9119.7 (4)O7—C27—H27A109.5
C13—C8—C14118.4 (3)O7—C27—H27B109.5
C9—C8—C14121.7 (3)H27A—C27—H27B109.5
O2—C9—C10118.1 (3)O7—C27—H27C109.5
O2—C9—C8124.7 (3)H27A—C27—H27C109.5
C10—C9—C8117.2 (3)H27B—C27—H27C109.5

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2742).

References

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