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Acta Crystallogr Sect E Struct Rep Online. 2009 April 1; 65(Pt 4): m468.
Published online 2009 March 31. doi:  10.1107/S1600536809011167
PMCID: PMC2968959

Aqua­chlorido{6,6′-dimeth­oxy-2,2′-[ethane-1,2-diylbis(nitrilo­dimethyl­idyne)]diphenolato-κ2 O 1,N,N′,O 1′}cobalt(III) monohydrate

Abstract

The title compound, [Co(C18H18N2O4)Cl(H2O)]·H2O, contains a distorted octa­hedral cobalt(III) complex with a 6,6′-dimeth­oxy-2,2′-[ethane-1,2-diylbis(nitrilo­dimethyl­idyne)]diphenolate ligand, a chloride and an aqua ligand, and also a disordered water solvent mol­ecule (half-occupancy). The CoIII ion is coordinated in an N2O3Cl manner. Weak O—H(...)O hydrogen bonds may help to stabilize the crystal packing.

Related literature

For related literature, see: Aurangzeb et al. (1994 [triangle]); Hulme et al. (1997 [triangle]); Li et al. (2008 [triangle]); Fei & Fang (2008 [triangle]); Wang et al. (1979 [triangle]); Xia et al. (2007 [triangle]); Zhang & Janiak (2001 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0m468-scheme1.jpg

Experimental

Crystal data

  • [Co(C18H18N2O4)Cl(H2O)]·H2O
  • M r = 456.76
  • Trigonal, An external file that holds a picture, illustration, etc.
Object name is e-65-0m468-efi1.jpg
  • a = 26.490 (2) Å
  • c = 15.6234 (17) Å
  • V = 9494.5 (14) Å3
  • Z = 18
  • Mo Kα radiation
  • μ = 0.98 mm−1
  • T = 293 K
  • 0.15 × 0.13 × 0.09 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003 [triangle]) T min = 0.868, T max = 0.917
  • 13737 measured reflections
  • 4116 independent reflections
  • 2834 reflections with I > 2σ(I)
  • R int = 0.062

Refinement

  • R[F 2 > 2σ(F 2)] = 0.074
  • wR(F 2) = 0.259
  • S = 1.03
  • 4116 reflections
  • 274 parameters
  • H-atom parameters constrained
  • Δρmax = 1.55 e Å−3
  • Δρmin = −1.03 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: XP (Sheldrick, 1998 [triangle]); software used to prepare material for publication: XP.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809011167/hg2491sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809011167/hg2491Isup2.hkl

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

supplementary crystallographic information

Comment

The synthesis and structural investigation of Schiff base complexes have attracted much attention due to their interesting structures and wide potential applications. They play an important role in the development of coordination chemistry as well as inorganic biochemistry, catalysis, optical materials and so on (Aurangzeb et al., 1994, Hulme et al., 1997; Li et al., 2008; Fei & Fang, 2008; Zhang & Janiak, 2001). Here, we report a new Schiff base cobalt complex based on the tetradentate Schiff base ligand 6,6'-dimethoxy-2,2'-(ethane-1,2-diyldiiminodimethylene)diphenol.

The molecular structure of title compound is shown in Fig. 1. The coordination sphere for the CoIII ion in the title complex is a distorted octahedron, in which four equational positions come from two N atoms, two O atoms of the Schiff base ligand, and the other two trans ones are occupied by one chloro ion and the O atom of water molecule. The Co—O and Co—N bond lengths are basically consistent with the corresponding distances in the similar cobalt tetradentate Schiff base complex bis[[µ-bis(salicylaldehyde)ethylenediimine]-dicobalt(III) dichloride chloroform solvate(Wang, et al., 1979), while the Co—O (H2O) and the Co—Cl bond lengths are slightly longer than those found in the same complex. Additional, molecules are held together via intermolecular O—H···O and intramolecular O—H···Cl and O—H···O hydrogen bonds.

Experimental

6,6'-dimethoxy-2,2'-(ethane-1,2-diyldiiminodimethylene)diphenol was synthesized according to a modified reported method (Xia, et al., 2007). A mixture of CoCl2.6H2O (1 mmol, 237 mg), 6,6'-dimethoxy-2,2'-(ethane-1,2-diyldiiminodimethylene)diphenol (1 mmol, 326.4 mg) and 40 ml methanol was stirred for 30 min at 323 K, before it was filtered to remove the insolvable materials. Crystals suitable for X-ray diffraction analysis were obtained by slow evaparation at room temperature for three weeks with a yield about 40%.

Refinement

All H atoms bonded to the C atoms were placed in geometrically calculated positions with C—H = 0.96 Å for methyl H atoms, C—H = 0.97 Å for methylene H atoms, C—H = 0.93 Å for aromatic H atoms and were refined isotropic with Uiso(H) = 1.2Ueq(C) or Uiso(H) = 1.5Ueq(C) of parent atom using a riding model. The H atoms of the disordered H2O were located from difference maps, in which the H2B and H2C were also disordered with the individual occupancy of 25%, and the O—H bond lengths were constrained to the value of 0.85 (1)Å with Uiso(H) = 1.2Ueq(O).

Figures

Fig. 1.
A view of complex (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme. The solvate water molecule and all the H atoms have been omitted for clarity.

Crystal data

[Co(C18H18N2O4)Cl(H2O)]·H2ODx = 1.438 Mg m3Dm = 1.438 Mg m3Dm measured by not measured
Mr = 456.76Mo Kα radiation, λ = 0.71073 Å
Trigonal, R3Cell parameters from 5356 reflections
Hall symbol: -R 3θ = 2.7–26.9°
a = 26.490 (2) ŵ = 0.98 mm1
c = 15.6234 (17) ÅT = 293 K
V = 9494.5 (14) Å3Block, orange
Z = 180.15 × 0.13 × 0.09 mm
F(000) = 4248

Data collection

Bruker APEXII CCD area-detector diffractometer4116 independent reflections
Radiation source: fine-focus sealed tube2834 reflections with I > 2σ(I)
graphiteRint = 0.062
[var phi] and ω scansθmax = 26.2°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)h = −28→32
Tmin = 0.868, Tmax = 0.917k = −32→25
13737 measured reflectionsl = −19→12

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)] = 0.074Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.259H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.1835P)2] where P = (Fo2 + 2Fc2)/3
4116 reflections(Δ/σ)max = 0.001
274 parametersΔρmax = 1.55 e Å3
0 restraintsΔρmin = −1.03 e Å3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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*/UeqOcc. (<1)
Co10.73792 (3)0.12280 (3)0.59262 (4)0.0357 (3)
Cl10.62851 (7)0.08016 (8)0.61355 (10)0.0637 (5)
O10.5945 (14)0.144 (3)0.478 (3)0.057 (16)0.15 (3)
H1C0.61270.16360.43550.068*0.15 (3)
H1D0.61440.13050.50140.068*0.15 (3)
O80.5817 (6)0.1059 (11)0.4435 (11)0.058 (7)0.35 (3)
H8E0.59710.14060.42410.069*0.35 (3)
H8D0.59900.10680.48870.069*0.35 (3)
O20.7381 (4)0.2826 (4)0.3172 (5)0.055 (2)0.50
H2C0.75320.27730.27350.066*0.25
H2D0.75390.31930.32580.066*0.50
H2B0.70120.26750.31090.066*0.25
O30.74870 (15)0.07928 (14)0.6768 (2)0.0349 (8)
O40.76146 (16)0.18833 (15)0.6619 (2)0.0404 (8)
O50.77398 (18)0.04171 (17)0.8092 (2)0.0481 (9)
O60.78604 (19)0.25833 (17)0.7866 (3)0.0552 (10)
O70.83443 (14)0.15912 (15)0.5522 (2)0.0401 (8)
H7C0.85520.15390.58810.048*
H7D0.84990.19580.54340.048*
N10.71890 (18)0.06087 (19)0.5088 (2)0.0376 (9)
N20.73614 (19)0.1675 (2)0.4961 (3)0.0422 (10)
C10.7312 (2)−0.0054 (2)0.5961 (3)0.0417 (12)
C20.7457 (2)0.0273 (2)0.6710 (3)0.0352 (10)
C30.7579 (3)0.0050 (2)0.7421 (3)0.0429 (12)
C40.7545 (3)−0.0489 (3)0.7403 (4)0.0608 (17)
H40.7633−0.06280.78940.073*
C50.7387 (4)−0.0815 (3)0.6683 (5)0.074 (2)
H50.7354−0.11810.66850.088*
C60.7280 (3)−0.0612 (3)0.5979 (5)0.0592 (16)
H60.7182−0.08350.54820.071*
C70.7192 (2)0.0129 (2)0.5214 (3)0.0399 (11)
H70.7102−0.01180.47450.048*
C80.7796 (3)0.0185 (4)0.8876 (4)0.070 (2)
H8A0.7445−0.01770.89880.104*
H8B0.78610.04560.93290.104*
H8C0.81200.01180.88440.104*
C90.7448 (2)0.2507 (3)0.5713 (4)0.0462 (12)
C100.7583 (2)0.2354 (2)0.6479 (3)0.0406 (12)
C110.7708 (3)0.2746 (2)0.7164 (4)0.0473 (13)
C120.7685 (3)0.3254 (3)0.7061 (5)0.0666 (18)
H120.77660.35030.75250.080*
C130.7547 (4)0.3394 (3)0.6299 (6)0.079 (2)
H130.75270.37330.62430.095*
C140.7439 (3)0.3038 (3)0.5620 (5)0.0635 (17)
H140.73580.31400.50890.076*
C150.8063 (3)0.2980 (3)0.8565 (4)0.0628 (18)
H15A0.84270.33180.84150.094*
H15B0.81170.27950.90560.094*
H15C0.77810.30960.86950.094*
C160.7376 (3)0.2170 (3)0.4987 (4)0.0477 (13)
H160.73340.23170.44680.057*
C170.7351 (3)0.1387 (3)0.4155 (3)0.0537 (15)
H17A0.77450.15080.39750.064*
H17B0.71660.14960.37120.064*
C180.7020 (3)0.0749 (3)0.4289 (3)0.0537 (14)
H18A0.66060.06130.42940.064*
H18B0.70990.05550.38240.064*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Co10.0441 (5)0.0379 (4)0.0280 (4)0.0226 (3)−0.0021 (3)−0.0013 (2)
Cl10.0478 (9)0.0909 (12)0.0596 (10)0.0402 (9)0.0133 (7)0.0135 (8)
O10.053 (18)0.08 (3)0.05 (2)0.04 (2)0.001 (14)0.02 (2)
O80.054 (8)0.079 (15)0.050 (9)0.041 (9)0.001 (6)0.023 (9)
O20.059 (5)0.064 (5)0.038 (4)0.028 (4)−0.016 (3)−0.006 (4)
O30.048 (2)0.0316 (17)0.0316 (16)0.0247 (16)−0.0040 (14)−0.0019 (13)
O40.055 (2)0.0358 (19)0.0366 (18)0.0271 (17)−0.0075 (15)−0.0045 (14)
O50.067 (3)0.050 (2)0.0366 (19)0.036 (2)−0.0030 (17)0.0073 (16)
O60.070 (3)0.041 (2)0.052 (2)0.025 (2)−0.0006 (19)−0.0114 (17)
O70.039 (2)0.0397 (19)0.0370 (19)0.0165 (16)−0.0023 (14)0.0003 (14)
N10.035 (2)0.044 (2)0.031 (2)0.0166 (19)−0.0035 (16)−0.0091 (17)
N20.043 (2)0.052 (3)0.033 (2)0.025 (2)−0.0031 (18)0.0039 (18)
C10.040 (3)0.033 (3)0.051 (3)0.018 (2)−0.001 (2)−0.009 (2)
C20.032 (2)0.033 (2)0.043 (3)0.018 (2)0.0029 (19)0.0007 (19)
C30.052 (3)0.040 (3)0.041 (3)0.027 (3)0.004 (2)0.008 (2)
C40.083 (5)0.048 (4)0.063 (4)0.041 (4)−0.004 (3)0.008 (3)
C50.100 (6)0.042 (4)0.091 (6)0.044 (4)−0.014 (4)−0.005 (3)
C60.072 (4)0.038 (3)0.070 (4)0.029 (3)−0.002 (3)−0.013 (3)
C70.035 (3)0.037 (3)0.041 (3)0.014 (2)−0.004 (2)−0.015 (2)
C80.096 (5)0.088 (5)0.038 (3)0.056 (5)0.000 (3)0.018 (3)
C90.044 (3)0.047 (3)0.055 (3)0.028 (3)−0.001 (2)0.007 (2)
C100.040 (3)0.035 (3)0.052 (3)0.021 (2)0.004 (2)0.002 (2)
C110.047 (3)0.038 (3)0.057 (3)0.021 (3)0.002 (2)−0.005 (2)
C120.082 (5)0.046 (4)0.080 (5)0.039 (4)−0.002 (4)−0.011 (3)
C130.093 (6)0.051 (4)0.108 (6)0.047 (4)−0.005 (5)0.003 (4)
C140.068 (4)0.055 (4)0.079 (4)0.040 (3)−0.003 (3)0.008 (3)
C150.060 (4)0.053 (4)0.056 (4)0.014 (3)0.002 (3)−0.023 (3)
C160.047 (3)0.053 (3)0.046 (3)0.026 (3)−0.005 (2)0.013 (2)
C170.064 (4)0.063 (4)0.029 (3)0.028 (3)−0.005 (2)−0.001 (2)
C180.062 (4)0.066 (4)0.033 (3)0.032 (3)−0.008 (2)−0.009 (3)

Geometric parameters (Å, °)

Co1—O31.863 (3)C2—C31.370 (7)
Co1—O41.868 (3)C3—C41.385 (8)
Co1—N21.932 (4)C4—C51.350 (9)
Co1—N11.957 (4)C4—H40.9300
Co1—O72.324 (3)C5—C61.315 (10)
Co1—Cl12.5513 (17)C5—H50.9300
O1—H1C0.8381C6—H60.9300
O1—H1D0.8514C7—H70.9300
O1—H8E0.8596C8—H8A0.9600
O1—H8D1.0649C8—H8B0.9600
O8—H1D1.1965C8—H8C0.9600
O8—H8E0.8530C9—C101.367 (8)
O8—H8D0.8360C9—C161.396 (8)
O2—H2C0.8374C9—C141.426 (8)
O2—H2D0.8561C10—C111.411 (8)
O2—H2B0.8563C11—C121.385 (9)
O3—C21.342 (6)C12—C131.350 (11)
O4—C101.309 (6)C12—H120.9300
O5—C31.347 (7)C13—C141.352 (10)
O5—C81.412 (7)C13—H130.9300
O6—C111.314 (7)C14—H140.9300
O6—C151.422 (7)C15—H15A0.9600
O7—H7C0.8439C15—H15B0.9600
O7—H7D0.8561C15—H15C0.9600
N1—C71.290 (7)C16—H160.9300
N1—C181.436 (7)C17—C181.480 (9)
N2—C161.294 (8)C17—H17A0.9700
N2—C171.465 (7)C17—H17B0.9700
C1—C71.362 (7)C18—H18A0.9700
C1—C21.391 (7)C18—H18B0.9700
C1—C61.438 (8)
O3—Co1—O494.76 (14)C6—C5—C4119.7 (6)
O3—Co1—N2171.32 (17)C6—C5—H5120.1
O4—Co1—N288.92 (18)C4—C5—H5120.1
O3—Co1—N190.48 (16)C5—C6—C1121.5 (6)
O4—Co1—N1172.92 (17)C5—C6—H6119.3
N2—Co1—N185.24 (18)C1—C6—H6119.3
O3—Co1—O788.31 (14)N1—C7—C1126.8 (5)
O4—Co1—O789.17 (15)N1—C7—H7116.6
N2—Co1—O783.87 (16)C1—C7—H7116.6
N1—Co1—O786.23 (15)O5—C8—H8A109.5
O3—Co1—Cl197.31 (12)O5—C8—H8B109.5
O4—Co1—Cl196.58 (13)H8A—C8—H8B109.5
N2—Co1—Cl190.05 (14)O5—C8—H8C109.5
N1—Co1—Cl187.44 (13)H8A—C8—H8C109.5
O7—Co1—Cl1171.56 (10)H8B—C8—H8C109.5
H1C—O1—H1D108.1C10—C9—C16119.6 (5)
H1C—O1—H8E39.0C10—C9—C14121.2 (6)
H1D—O1—H8E105.8C16—C9—C14118.9 (5)
H1C—O1—H8D113.4O4—C10—C9125.4 (5)
H1D—O1—H8D33.5O4—C10—C11118.2 (5)
H8E—O1—H8D89.9C9—C10—C11116.4 (5)
H1C—O8—H1D65.3O6—C11—C12125.9 (6)
H1C—O8—H8E16.5O6—C11—C10112.8 (5)
H1D—O8—H8E81.6C12—C11—C10121.2 (6)
H1C—O8—H8D91.9C13—C12—C11121.3 (6)
H1D—O8—H8D26.9C13—C12—H12119.4
H8E—O8—H8D108.1C11—C12—H12119.4
H2C—O2—H2D108.4C12—C13—C14119.5 (6)
H2C—O2—H2B111.0C12—C13—H13120.2
H2D—O2—H2B110.1C14—C13—H13120.2
C2—O3—Co1129.7 (3)C13—C14—C9120.3 (7)
C10—O4—Co1129.6 (3)C13—C14—H14119.8
C3—O5—C8115.2 (5)C9—C14—H14119.8
C11—O6—C15117.5 (5)O6—C15—H15A109.5
Co1—O7—H7C115.1O6—C15—H15B109.5
Co1—O7—H7D108.4H15A—C15—H15B109.5
H7C—O7—H7D108.2O6—C15—H15C109.5
C7—N1—C18122.9 (4)H15A—C15—H15C109.5
C7—N1—Co1126.7 (3)H15B—C15—H15C109.5
C18—N1—Co1110.4 (4)N2—C16—C9126.8 (5)
C16—N2—C17122.5 (5)N2—C16—H16116.6
C16—N2—Co1126.9 (4)C9—C16—H16116.6
C17—N2—Co1110.6 (4)N2—C17—C18108.7 (5)
C7—C1—C2122.6 (5)N2—C17—H17A110.0
C7—C1—C6118.7 (5)C18—C17—H17A110.0
C2—C1—C6118.7 (5)N2—C17—H17B110.0
O3—C2—C3118.8 (4)C18—C17—H17B110.0
O3—C2—C1123.6 (5)H17A—C17—H17B108.3
C3—C2—C1117.6 (5)N1—C18—C17109.6 (5)
O5—C3—C2112.2 (4)N1—C18—H18A109.7
O5—C3—C4126.4 (5)C17—C18—H18A109.7
C2—C3—C4121.4 (5)N1—C18—H18B109.7
C5—C4—C3121.0 (6)C17—C18—H18B109.7
C5—C4—H4119.5H18A—C18—H18B108.2
C3—C4—H4119.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O7—H7D···O3i0.862.442.883 (5)113
O7—H7D···O5i0.862.223.078 (5)178
O7—H7C···O6i0.842.583.033 (6)115
O7—H7C···O4i0.841.952.798 (5)178
O2—H2D···O2ii0.862.012.861 (9)178
O2—H2C···O8ii0.842.132.868 (19)147
O2—H2C···O1ii0.841.722.56 (3)175
O8—H8E···O2iii0.852.042.868 (19)163
O8—H8D···Cl10.842.343.147 (12)163
O1—H1D···Cl10.852.343.11 (3)150

Symmetry codes: (i) −x+5/3, −y+1/3, −z+4/3; (ii) xy+1/3, x−1/3, −z+2/3; (iii) y+1/3, −x+y+2/3, −z+2/3.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2491).

References

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