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Acta Crystallogr Sect E Struct Rep Online. 2010 April 1; 66(Pt 4): m366–m367.
Published online 2010 March 6. doi:  10.1107/S1600536810007622
PMCID: PMC2983841

{6,6′-Dieth­oxy-2,2′-[2,2-dimethyl­propane-1,3-diylbis(nitrilo­methyl­idyne)]diphenolato}(2-eth­oxy-6-formyl­phenolato)cobalt(III)–ethanol–water (1/1/1)

Abstract

The asymmetric unit of the title compound, [Co(C23H28N2O4)(C9H9O3)]·C2H5OH·H2O, comprises one complex mol­ecule, a water mol­ecule of crystallization and an ethanol mol­ecule of crystallization, which is disordered over two positions with a ratio of refined site occupancies of 0.567 (10):0.433 (10). The CoIII ion is in a slightly distorted octa­hedral geometry involving an N2O2 atom set of the tetra­denate Schiff base ligand and two O atoms of 2-eth­oxy-6-formyl­phenolate. The H atoms of the water mol­ecule act as donors in the formation of bifurcated inter­molecular O—H(...)(O,O) hydrogen bonds with the O atoms of the hydr­oxy and eth­oxy groups with R 1 2(5) ring motifs, which may influence the mol­ecular conformation. The crystal structure is further stabilized by inter­molecular O—H(...)O and C—H(...)O inter­actions.

Related literature

For hydrogen-bond motifs, see: Bernstein et al. (1995 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]). For background to Schiff base–metal complexes, see: Granovski et al. (1993 [triangle]); Blower et al. (1998 [triangle]); Elmali et al. (2000 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m366-scheme1.jpg

Experimental

Crystal data

  • [Co(C23H28N2O4)(C9H9O3)]·C2H6O·H2O
  • M r = 684.65
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m366-efi1.jpg
  • a = 13.2827 (17) Å
  • b = 14.0158 (17) Å
  • c = 19.602 (2) Å
  • β = 106.491 (7)°
  • V = 3499.1 (8) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.54 mm−1
  • T = 298 K
  • 0.42 × 0.21 × 0.15 mm

Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.804, T max = 0.923
  • 69893 measured reflections
  • 6159 independent reflections
  • 3652 reflections with I > 2σ(I)
  • R int = 0.115

Refinement

  • R[F 2 > 2σ(F 2)] = 0.051
  • wR(F 2) = 0.138
  • S = 1.05
  • 6159 reflections
  • 424 parameters
  • 6 restraints
  • H-atom parameters constrained
  • Δρmax = 0.35 e Å−3
  • Δρmin = −0.38 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810007622/jh2132sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810007622/jh2132Isup2.hkl

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

Acknowledgments

HK and RK thank PNU for the financial support. RK and KZ also thank the Science and Research Branch, Islamic Azad University. IUK thanks GC University of Lahore, for the research facilities.

supplementary crystallographic information

Comment

Schiff base complexes are one of the most important stereochemical models in transition metal coordination chemistry, with the ease of preparation and structural variations (Granovski et al., 1993). Metal derivatives of the Schiff bases have been studied extensively, and they play a major role in both synthetic and structurel research (Elmali et al., 2000; Blower et al., 1998). The structure of the title compound was determined to clarify the identity of the synthesis product.

The asymmetric unit of the title compound, Fig. 1, [Co(C32H37N2O7)]. C2H6O. H2O, comprises a unit of the complex, a water molecule of crystallization and an ethanol of crystallization. The H atoms of the water molecule act as donors in the formation of bifurcated O—H···(O,O) intermolecular hydrogen bonds with the O atoms of the hydroxy and ethoxy groups with R21(5) ring motifs (Bernstein et al., 1995) which may influence the molecular conformation. The crystal structure is further stabilized by the intermolecular C—H···O and O—H···O interactions (Table 1).

Experimental

The title compound was synthesized by adding 6,6'-Diethoxy-2,2'- [2,3-dimethyl-propylenebis(nitrilomethylidyne)]-diphenol (2 mmol) to a solution of CoCl2. 6 H2O (2 mmol) in ethanol (30 ml). The mixture was refluxed with stirring for half an hour. The resultant red solution was filtered. Brown single crystals of the title compound suitable for X-ray structure determination were recrystallized from ethanol by slow evaporation of the solvents at room temperature over several days.

Refinement

The H atoms of the water molecule were located in a difference Fourier map and constrained to refine with the parent atom with Uiso(H) = 1.5 Ueq(O). The H atoms of the ethanol molecules were positioned geometrically and constrained to refine with the parent atoms with Uiso(H) = 1.5 Ueq(O). The rest of the H atoms were positioned geometrically and refined using a riding model with Uiso(H) = 1.2 or 1.5 Ueq(C). Distant restraints were applied to the ethanol molecules.

Figures

Fig. 1.
The asymmetric unit of the title compound, showing 30% probability displacement ellipsoids and the atomic numbering. All H atoms except those of water and ethanol molecules were omitted for clarity. Intramolecular hydrogen bonds are drawn as dashed lines. ...

Crystal data

[Co(C23H28N2O4)(C9H9O3)]·C2H6O·H2OF(000) = 1448
Mr = 684.65Dx = 1.300 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6054 reflections
a = 13.2827 (17) Åθ = 2.6–18.8°
b = 14.0158 (17) ŵ = 0.54 mm1
c = 19.602 (2) ÅT = 298 K
β = 106.491 (7)°Block, brown
V = 3499.1 (8) Å30.42 × 0.21 × 0.15 mm
Z = 4

Data collection

Bruker SMART APEXII CCD area-detector diffractometer6159 independent reflections
Radiation source: fine-focus sealed tube3652 reflections with I > 2σ(I)
graphiteRint = 0.115
[var phi] and ω scansθmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)h = −15→15
Tmin = 0.804, Tmax = 0.923k = −16→16
69893 measured reflectionsl = −23→23

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)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0534P)2 + 2.3725P] where P = (Fo2 + 2Fc2)/3
6159 reflections(Δ/σ)max = 0.001
424 parametersΔρmax = 0.35 e Å3
6 restraintsΔρmin = −0.38 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)
Co10.08603 (4)0.66689 (3)0.10882 (3)0.03716 (18)
O10.16611 (19)0.55376 (17)0.11696 (13)0.0400 (6)
O20.1630 (2)0.71434 (17)0.04880 (13)0.0420 (7)
O30.0100 (2)0.78205 (17)0.09545 (13)0.0440 (7)
O40.3340 (2)0.4494 (2)0.13168 (16)0.0633 (8)
O50.2931 (2)0.7862 (2)−0.01411 (17)0.0634 (9)
O6−0.1080 (2)0.92553 (19)0.04635 (16)0.0558 (8)
N10.0146 (3)0.6214 (2)0.17440 (16)0.0411 (8)
N2−0.0255 (2)0.6182 (2)0.03404 (16)0.0360 (7)
O70.1986 (2)0.71601 (19)0.18559 (13)0.0471 (7)
C10.1982 (3)0.5046 (3)0.1762 (2)0.0401 (9)
C170.1290 (3)0.7202 (2)−0.0207 (2)0.0390 (10)
C300.0521 (3)0.8646 (3)0.1149 (2)0.0409 (10)
C10−0.1038 (3)0.5570 (3)0.0523 (2)0.0441 (10)
H10A−0.06820.50280.07940.053*
H10B−0.15170.53280.00870.053*
C120.0297 (3)0.6901 (2)−0.0623 (2)0.0400 (10)
C60.1477 (3)0.5041 (3)0.2303 (2)0.0463 (10)
C11−0.0402 (3)0.6393 (2)−0.0321 (2)0.0399 (10)
H11−0.10320.6192−0.06340.048*
C32−0.1803 (4)1.0022 (3)0.0196 (3)0.0634 (13)
H32A−0.15571.0412−0.01320.076*
H32B−0.18701.04220.05850.076*
C160.1978 (4)0.7582 (3)−0.0578 (2)0.0477 (11)
C25−0.0104 (4)0.9476 (3)0.0882 (2)0.0450 (10)
C8−0.0929 (3)0.6532 (3)0.1644 (2)0.0487 (11)
H8C−0.09600.72220.16070.058*
H8B−0.11590.63480.20530.058*
C70.0531 (3)0.5571 (3)0.2221 (2)0.0492 (11)
H70.01540.54410.25440.059*
C290.1529 (3)0.8801 (3)0.1619 (2)0.0471 (10)
C20.2861 (3)0.4432 (3)0.1853 (2)0.0527 (11)
C130.0010 (4)0.6986 (3)−0.1375 (2)0.0547 (12)
H13−0.06540.6791−0.16420.066*
C280.1908 (4)0.9753 (3)0.1800 (2)0.0575 (12)
H280.25710.98530.21140.069*
C140.0689 (4)0.7348 (3)−0.1707 (2)0.0604 (13)
H140.04940.7397−0.22010.073*
C9−0.1676 (3)0.6083 (3)0.0956 (2)0.0484 (11)
C310.2158 (3)0.8032 (3)0.1952 (2)0.0521 (11)
H310.27840.81940.22880.063*
C50.1836 (4)0.4445 (4)0.2893 (2)0.0670 (14)
H50.14930.44440.32460.080*
C30.3193 (4)0.3866 (3)0.2438 (3)0.0720 (14)
H3A0.37730.34730.24890.086*
C270.1302 (4)1.0495 (3)0.1514 (3)0.0645 (14)
H270.15581.11100.16230.077*
C150.1682 (4)0.7648 (3)−0.1310 (2)0.0622 (13)
H150.21480.7895−0.15400.075*
C22−0.2350 (4)0.5316 (4)0.1163 (3)0.0779 (16)
H22D−0.28050.50350.07410.117*
H22E−0.27640.55980.14390.117*
H22C−0.19040.48330.14400.117*
C40.2673 (5)0.3872 (4)0.2957 (3)0.0826 (17)
H40.29020.34780.33530.099*
C260.0291 (4)1.0369 (3)0.1054 (2)0.0570 (12)
H26−0.01131.08990.08640.068*
C23−0.2355 (4)0.6871 (4)0.0513 (3)0.0736 (15)
H23A−0.28140.66000.00880.110*
H23B−0.19110.73390.03880.110*
H23C−0.27650.71690.07860.110*
C180.4309 (4)0.3987 (4)0.1404 (3)0.0895 (17)
H18A0.41710.33090.13360.107*
H18B0.47670.40850.18810.107*
C33−0.2833 (4)0.9583 (4)−0.0174 (3)0.0921 (18)
H33E−0.33251.0074−0.03880.138*
H33D−0.30910.92340.01630.138*
H33C−0.27470.9156−0.05370.138*
C190.4820 (5)0.4348 (5)0.0872 (4)0.1229 (17)
H19D0.54390.39800.08990.184*
H19E0.50100.50060.09700.184*
H19C0.43420.42930.04040.184*
C200.3736 (4)0.8077 (4)−0.0458 (3)0.099 (2)
H20C0.35760.8665−0.07300.119*
H20B0.38050.7568−0.07770.119*
C210.4742 (5)0.8185 (5)0.0139 (4)0.1229 (17)
H21D0.53270.8221−0.00560.184*
H21B0.48280.76440.04510.184*
H21E0.47100.87570.04010.184*
O1W0.3766 (3)0.6483 (3)0.1020 (2)0.1109 (15)
H1WA0.34380.59750.10610.166*
H1WB0.33310.68570.07440.166*
O7B0.500 (3)0.7112 (17)0.2156 (14)0.187 (8)0.433 (10)
H7B0.51100.70290.17690.281*0.433 (10)
C34B0.483 (2)0.614 (2)0.3126 (16)0.226 (9)0.433 (10)
H34H0.51000.64870.35610.338*0.433 (10)
H34G0.48720.54660.32260.338*0.433 (10)
H34C0.41050.63100.29160.338*0.433 (10)
C35B0.5463 (16)0.6375 (16)0.2612 (12)0.138 (5)0.433 (10)
H35E0.61680.65600.28800.166*0.433 (10)
H35B0.55150.58130.23350.166*0.433 (10)
O7A0.4612 (19)0.7350 (11)0.2408 (10)0.187 (8)0.567 (10)
H7A0.43790.72120.19860.281*0.567 (10)
C34A0.5407 (18)0.5896 (16)0.2956 (15)0.226 (9)0.567 (10)
H34B0.54350.55130.33670.338*0.567 (10)
H34D0.60490.62490.30350.338*0.567 (10)
H34A0.53170.54910.25490.338*0.567 (10)
C35A0.4496 (10)0.6580 (10)0.2828 (9)0.138 (5)0.567 (10)
H35A0.38520.62450.25960.166*0.567 (10)
H35C0.44400.68150.32820.166*0.567 (10)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Co10.0447 (3)0.0301 (3)0.0365 (3)−0.0004 (3)0.0113 (2)−0.0034 (2)
O10.0476 (17)0.0347 (14)0.0375 (15)0.0035 (12)0.0118 (13)−0.0009 (12)
O20.0439 (17)0.0405 (15)0.0408 (16)−0.0030 (13)0.0109 (13)0.0034 (12)
O30.0494 (18)0.0260 (14)0.0538 (17)−0.0013 (12)0.0101 (14)−0.0069 (12)
O40.056 (2)0.066 (2)0.071 (2)0.0214 (16)0.0230 (18)0.0092 (17)
O50.054 (2)0.067 (2)0.077 (2)−0.0061 (17)0.0308 (19)0.0121 (17)
O60.059 (2)0.0381 (16)0.070 (2)0.0076 (15)0.0171 (17)0.0010 (14)
N10.046 (2)0.0384 (18)0.0389 (19)0.0002 (16)0.0124 (16)−0.0070 (16)
N20.044 (2)0.0275 (16)0.0386 (19)0.0012 (15)0.0144 (16)−0.0034 (14)
O70.0524 (18)0.0415 (17)0.0427 (16)−0.0020 (14)0.0058 (14)−0.0032 (13)
C10.045 (3)0.035 (2)0.037 (2)−0.0011 (19)0.006 (2)0.0004 (18)
C170.055 (3)0.025 (2)0.040 (2)0.0093 (18)0.017 (2)0.0008 (17)
C300.051 (3)0.034 (2)0.044 (2)−0.0012 (19)0.024 (2)−0.0052 (18)
C100.049 (3)0.037 (2)0.045 (2)−0.0064 (19)0.011 (2)−0.0042 (19)
C120.058 (3)0.024 (2)0.038 (2)0.0021 (18)0.014 (2)0.0007 (16)
C60.054 (3)0.044 (2)0.041 (2)0.005 (2)0.015 (2)0.005 (2)
C110.047 (3)0.028 (2)0.039 (2)0.0034 (18)0.003 (2)−0.0072 (17)
C320.077 (4)0.047 (3)0.074 (3)0.021 (3)0.034 (3)0.015 (2)
C160.054 (3)0.036 (2)0.057 (3)0.005 (2)0.022 (2)0.004 (2)
C250.056 (3)0.035 (2)0.051 (3)0.002 (2)0.027 (2)−0.0046 (19)
C80.048 (3)0.052 (3)0.051 (2)0.001 (2)0.022 (2)−0.006 (2)
C70.061 (3)0.053 (3)0.038 (2)−0.008 (2)0.021 (2)−0.005 (2)
C290.061 (3)0.042 (2)0.041 (2)−0.005 (2)0.019 (2)−0.007 (2)
C20.053 (3)0.047 (3)0.058 (3)0.002 (2)0.013 (2)0.006 (2)
C130.080 (3)0.038 (2)0.044 (3)0.005 (2)0.014 (2)0.002 (2)
C280.065 (3)0.043 (3)0.068 (3)−0.018 (2)0.026 (3)−0.014 (2)
C140.090 (4)0.048 (3)0.044 (3)0.006 (3)0.020 (3)0.005 (2)
C90.040 (3)0.048 (3)0.059 (3)−0.002 (2)0.017 (2)−0.007 (2)
C310.055 (3)0.055 (3)0.042 (2)−0.012 (2)0.007 (2)−0.010 (2)
C50.076 (4)0.076 (3)0.050 (3)0.006 (3)0.019 (3)0.020 (3)
C30.072 (4)0.066 (3)0.074 (3)0.022 (3)0.013 (3)0.024 (3)
C270.087 (4)0.037 (3)0.075 (3)−0.018 (3)0.033 (3)−0.020 (2)
C150.089 (4)0.052 (3)0.057 (3)0.008 (3)0.039 (3)0.013 (2)
C220.067 (4)0.089 (4)0.089 (4)−0.028 (3)0.042 (3)−0.018 (3)
C40.089 (4)0.086 (4)0.067 (4)0.020 (3)0.013 (3)0.044 (3)
C260.075 (4)0.031 (2)0.075 (3)−0.002 (2)0.037 (3)−0.003 (2)
C230.064 (3)0.078 (4)0.071 (3)0.014 (3)0.007 (3)−0.014 (3)
C180.073 (4)0.087 (4)0.111 (5)0.029 (3)0.030 (4)0.005 (4)
C330.064 (4)0.086 (4)0.112 (5)0.017 (3)0.001 (3)0.011 (4)
C190.069 (3)0.137 (4)0.172 (5)−0.002 (3)0.050 (3)−0.001 (4)
C200.079 (4)0.098 (5)0.134 (5)0.000 (4)0.055 (4)0.016 (4)
C210.069 (3)0.137 (4)0.172 (5)−0.002 (3)0.050 (3)−0.001 (4)
O1W0.074 (3)0.105 (3)0.148 (4)0.000 (2)0.022 (3)0.045 (3)
O7B0.201 (19)0.138 (10)0.179 (14)−0.046 (8)−0.017 (10)−0.026 (10)
C34B0.20 (3)0.23 (2)0.21 (2)0.105 (17)−0.010 (18)−0.023 (16)
C35B0.119 (10)0.118 (11)0.142 (12)0.006 (9)−0.021 (9)−0.004 (8)
O7A0.201 (19)0.138 (10)0.179 (14)−0.046 (8)−0.017 (10)−0.026 (10)
C34A0.20 (3)0.23 (2)0.21 (2)0.105 (17)−0.010 (18)−0.023 (16)
C35A0.119 (10)0.118 (11)0.142 (12)0.006 (9)−0.021 (9)−0.004 (8)

Geometric parameters (Å, °)

Co1—O31.882 (2)C9—C221.525 (6)
Co1—O21.885 (3)C9—C231.531 (6)
Co1—O11.891 (2)C31—H310.9300
Co1—N21.891 (3)C5—C41.348 (6)
Co1—N11.910 (3)C5—H50.9300
Co1—O71.923 (3)C3—C41.382 (7)
O1—C11.313 (4)C3—H3A0.9300
O2—C171.311 (4)C27—C261.400 (6)
O3—C301.294 (4)C27—H270.9300
O4—C21.378 (5)C15—H150.9300
O4—C181.436 (5)C22—H22D0.9600
O5—C161.369 (5)C22—H22E0.9600
O5—C201.414 (6)C22—H22C0.9600
O6—C251.358 (5)C4—H40.9300
O6—C321.437 (5)C26—H260.9300
N1—C71.295 (5)C23—H23A0.9600
N1—C81.456 (5)C23—H23B0.9600
N2—C111.288 (4)C23—H23C0.9600
N2—C101.468 (5)C18—C191.486 (8)
O7—C311.247 (5)C18—H18A0.9700
C1—C61.405 (5)C18—H18B0.9700
C1—C21.421 (5)C33—H33E0.9600
C17—C121.404 (5)C33—H33D0.9600
C17—C161.423 (5)C33—H33C0.9600
C30—C291.410 (6)C19—H19D0.9600
C30—C251.440 (5)C19—H19E0.9600
C10—C91.538 (5)C19—H19C0.9600
C10—H10A0.9700C20—C211.514 (8)
C10—H10B0.9700C20—H20C0.9700
C12—C131.418 (5)C20—H20B0.9700
C12—C111.427 (5)C21—H21D0.9600
C6—C51.397 (6)C21—H21B0.9600
C6—C71.429 (6)C21—H21E0.9600
C11—H110.9300O1W—H1WA0.8508
C32—C331.487 (6)O1W—H1WB0.8508
C32—H32A0.9700O7B—C35B1.390 (10)
C32—H32B0.9700O7B—H7B0.8202
C16—C151.379 (6)O7B—H7A0.8084
C25—C261.361 (5)C34B—C35B1.526 (10)
C8—C91.561 (5)C34B—H34H0.9600
C8—H8C0.9700C34B—H34G0.9600
C8—H8B0.9700C34B—H34C0.9600
C7—H70.9300C35B—H35E0.9700
C29—C311.407 (6)C35B—H35B0.9700
C29—C281.434 (5)O7A—C35A1.392 (9)
C2—C31.360 (6)O7A—H7A0.8200
C13—C141.353 (6)C34A—C35A1.508 (9)
C13—H130.9300C34A—H34B0.9600
C28—C271.338 (6)C34A—H34D0.9600
C28—H280.9300C34A—H34A0.9600
C14—C151.392 (6)C35A—H35A0.9700
C14—H140.9300C35A—H35C0.9700
O3—Co1—O288.56 (11)C23—C9—C10110.6 (3)
O3—Co1—O1175.99 (11)C22—C9—C8109.4 (4)
O2—Co1—O187.52 (11)C23—C9—C8109.1 (3)
O3—Co1—N286.00 (12)C10—C9—C8110.5 (3)
O2—Co1—N295.04 (12)O7—C31—C29128.4 (4)
O1—Co1—N293.50 (11)O7—C31—H31115.8
O3—Co1—N191.77 (13)C29—C31—H31115.8
O2—Co1—N1176.57 (12)C4—C5—C6120.8 (5)
O1—Co1—N192.20 (12)C4—C5—H5119.6
N2—Co1—N188.39 (13)C6—C5—H5119.6
O3—Co1—O793.96 (11)C2—C3—C4120.5 (5)
O2—Co1—O785.60 (11)C2—C3—H3A119.8
O1—Co1—O786.58 (11)C4—C3—H3A119.8
N2—Co1—O7179.36 (13)C28—C27—C26121.7 (4)
N1—Co1—O790.97 (12)C28—C27—H27119.2
C1—O1—Co1123.2 (2)C26—C27—H27119.2
C17—O2—Co1125.7 (2)C16—C15—C14120.4 (4)
C30—O3—Co1123.8 (2)C16—C15—H15119.8
C2—O4—C18118.0 (4)C14—C15—H15119.8
C16—O5—C20117.8 (4)C9—C22—H22D109.5
C25—O6—C32118.3 (3)C9—C22—H22E109.5
C7—N1—C8118.8 (4)H22D—C22—H22E109.5
C7—N1—Co1123.3 (3)C9—C22—H22C109.5
C8—N1—Co1117.6 (3)H22D—C22—H22C109.5
C11—N2—C10117.6 (3)H22E—C22—H22C109.5
C11—N2—Co1123.9 (3)C5—C4—C3120.4 (4)
C10—N2—Co1118.4 (2)C5—C4—H4119.8
C31—O7—Co1122.5 (3)C3—C4—H4119.8
O1—C1—C6124.4 (4)C25—C26—C27120.5 (4)
O1—C1—C2118.5 (4)C25—C26—H26119.8
C6—C1—C2116.9 (4)C27—C26—H26119.8
O2—C17—C12125.1 (4)C9—C23—H23A109.5
O2—C17—C16118.3 (4)C9—C23—H23B109.5
C12—C17—C16116.6 (4)H23A—C23—H23B109.5
O3—C30—C29125.5 (4)C9—C23—H23C109.5
O3—C30—C25117.4 (4)H23A—C23—H23C109.5
C29—C30—C25117.1 (4)H23B—C23—H23C109.5
N2—C10—C9113.7 (3)O4—C18—C19108.7 (5)
N2—C10—H10A108.8O4—C18—H18A110.0
C9—C10—H10A108.8C19—C18—H18A110.0
N2—C10—H10B108.8O4—C18—H18B110.0
C9—C10—H10B108.8C19—C18—H18B110.0
H10A—C10—H10B107.7H18A—C18—H18B108.3
C17—C12—C13120.6 (4)C32—C33—H33E109.5
C17—C12—C11121.6 (3)C32—C33—H33D109.5
C13—C12—C11117.3 (4)H33E—C33—H33D109.5
C5—C6—C1120.3 (4)C32—C33—H33C109.5
C5—C6—C7119.0 (4)H33E—C33—H33C109.5
C1—C6—C7120.4 (4)H33D—C33—H33C109.5
N2—C11—C12127.0 (4)C18—C19—H19D109.5
N2—C11—H11116.5C18—C19—H19E109.5
C12—C11—H11116.5H19D—C19—H19E109.5
O6—C32—C33107.2 (4)C18—C19—H19C109.5
O6—C32—H32A110.3H19D—C19—H19C109.5
C33—C32—H32A110.3H19E—C19—H19C109.5
O6—C32—H32B110.3O5—C20—C21107.0 (5)
C33—C32—H32B110.3O5—C20—H20C110.3
H32A—C32—H32B108.5C21—C20—H20C110.3
O5—C16—C15124.9 (4)O5—C20—H20B110.3
O5—C16—C17113.6 (4)C21—C20—H20B110.3
C15—C16—C17121.5 (4)H20C—C20—H20B108.6
O6—C25—C26126.4 (4)C20—C21—H21D109.5
O6—C25—C30112.8 (3)C20—C21—H21B109.5
C26—C25—C30120.7 (4)H21D—C21—H21B109.5
N1—C8—C9110.7 (3)C20—C21—H21E109.5
N1—C8—H8C109.5H21D—C21—H21E109.5
C9—C8—H8C109.5H21B—C21—H21E109.5
N1—C8—H8B109.5H1WA—O1W—H1WB107.5
C9—C8—H8B109.5C35B—O7B—H7B109.1
H8C—C8—H8B108.1C35B—O7B—H7A127.3
N1—C7—C6126.6 (4)H7B—O7B—H7A94.1
N1—C7—H7116.7C35B—C34B—H34H109.5
C6—C7—H7116.7C35B—C34B—H34G109.5
C31—C29—C30120.9 (4)H34H—C34B—H34G109.5
C31—C29—C28118.5 (4)C35B—C34B—H34C109.5
C30—C29—C28120.5 (4)H34H—C34B—H34C109.5
C3—C2—O4124.8 (4)H34G—C34B—H34C109.5
C3—C2—C1121.1 (4)O7B—C35B—C34B111.1 (10)
O4—C2—C1114.0 (4)O7B—C35B—H35E109.4
C14—C13—C12120.8 (4)C34B—C35B—H35E109.4
C14—C13—H13119.6O7B—C35B—H35B109.4
C12—C13—H13119.6C34B—C35B—H35B109.4
C27—C28—C29119.5 (4)H35E—C35B—H35B108.0
C27—C28—H28120.3C35A—O7A—H7A109.9
C29—C28—H28120.3O7A—C35A—C34A111.9 (10)
C13—C14—C15119.9 (4)O7A—C35A—H35A109.2
C13—C14—H14120.0C34A—C35A—H35A109.2
C15—C14—H14120.0O7A—C35A—H35C109.2
C22—C9—C23111.4 (4)C34A—C35A—H35C109.2
C22—C9—C10105.9 (3)H35A—C35A—H35C107.9
O2—Co1—O1—C1142.6 (3)O2—C17—C16—O5−1.2 (5)
N2—Co1—O1—C1−122.5 (3)C12—C17—C16—O5179.9 (3)
N1—Co1—O1—C1−34.0 (3)O2—C17—C16—C15178.8 (4)
O7—Co1—O1—C156.8 (3)C12—C17—C16—C15−0.1 (5)
O3—Co1—O2—C17−76.0 (3)C32—O6—C25—C26−3.4 (6)
O1—Co1—O2—C17103.2 (3)C32—O6—C25—C30176.5 (3)
N2—Co1—O2—C179.9 (3)O3—C30—C25—O61.2 (5)
O7—Co1—O2—C17−170.1 (3)C29—C30—C25—O6−176.7 (3)
O2—Co1—O3—C30−62.5 (3)O3—C30—C25—C26−178.9 (4)
N2—Co1—O3—C30−157.7 (3)C29—C30—C25—C263.2 (6)
N1—Co1—O3—C30114.0 (3)C7—N1—C8—C9−103.9 (4)
O7—Co1—O3—C3022.9 (3)Co1—N1—C8—C969.2 (4)
O3—Co1—N1—C7−156.5 (3)C8—N1—C7—C6166.9 (4)
O1—Co1—N1—C724.1 (3)Co1—N1—C7—C6−5.8 (6)
N2—Co1—N1—C7117.5 (3)C5—C6—C7—N1173.3 (4)
O7—Co1—N1—C7−62.6 (3)C1—C6—C7—N1−12.9 (6)
O3—Co1—N1—C830.7 (3)O3—C30—C29—C31−3.1 (6)
O1—Co1—N1—C8−148.7 (3)C25—C30—C29—C31174.6 (4)
N2—Co1—N1—C8−55.3 (3)O3—C30—C29—C28−179.5 (4)
O7—Co1—N1—C8124.7 (3)C25—C30—C29—C28−1.8 (6)
O3—Co1—N2—C1174.6 (3)C18—O4—C2—C3−5.3 (7)
O2—Co1—N2—C11−13.6 (3)C18—O4—C2—C1172.6 (4)
O1—Co1—N2—C11−101.4 (3)O1—C1—C2—C3−176.3 (4)
N1—Co1—N2—C11166.5 (3)C6—C1—C2—C30.1 (6)
O3—Co1—N2—C10−101.8 (3)O1—C1—C2—O45.6 (5)
O2—Co1—N2—C10170.0 (2)C6—C1—C2—O4−178.0 (4)
O1—Co1—N2—C1082.2 (3)C17—C12—C13—C140.8 (6)
N1—Co1—N2—C10−9.9 (3)C11—C12—C13—C14−171.5 (4)
O3—Co1—O7—C31−20.5 (3)C31—C29—C28—C27−177.0 (4)
O2—Co1—O7—C3167.8 (3)C30—C29—C28—C27−0.6 (6)
O1—Co1—O7—C31155.5 (3)C12—C13—C14—C15−0.4 (6)
N1—Co1—O7—C31−112.3 (3)N2—C10—C9—C22−173.8 (3)
Co1—O1—C1—C626.2 (5)N2—C10—C9—C2365.4 (4)
Co1—O1—C1—C2−157.7 (3)N2—C10—C9—C8−55.5 (4)
Co1—O2—C17—C12−1.3 (5)N1—C8—C9—C22107.1 (4)
Co1—O2—C17—C16179.9 (2)N1—C8—C9—C23−130.9 (4)
Co1—O3—C30—C29−15.0 (5)N1—C8—C9—C10−9.2 (5)
Co1—O3—C30—C25167.2 (2)Co1—O7—C31—C2910.0 (6)
C11—N2—C10—C9−112.7 (4)C30—C29—C31—O75.7 (7)
Co1—N2—C10—C964.0 (4)C28—C29—C31—O7−177.9 (4)
O2—C17—C12—C13−179.3 (3)C1—C6—C5—C40.5 (7)
C16—C17—C12—C13−0.5 (5)C7—C6—C5—C4174.2 (5)
O2—C17—C12—C11−7.4 (6)O4—C2—C3—C4178.3 (5)
C16—C17—C12—C11171.4 (3)C1—C2—C3—C40.5 (7)
O1—C1—C6—C5175.6 (4)C29—C28—C27—C261.6 (7)
C2—C1—C6—C5−0.5 (6)O5—C16—C15—C14−179.6 (4)
O1—C1—C6—C72.0 (6)C17—C16—C15—C140.5 (6)
C2—C1—C6—C7−174.2 (4)C13—C14—C15—C16−0.2 (7)
C10—N2—C11—C12−174.1 (3)C6—C5—C4—C30.1 (8)
Co1—N2—C11—C129.5 (5)C2—C3—C4—C5−0.6 (8)
C17—C12—C11—N22.9 (6)O6—C25—C26—C27177.6 (4)
C13—C12—C11—N2175.1 (4)C30—C25—C26—C27−2.3 (6)
C25—O6—C32—C33−174.0 (4)C28—C27—C26—C25−0.2 (7)
C20—O5—C16—C15−11.7 (6)C2—O4—C18—C19−165.4 (4)
C20—O5—C16—C17168.2 (4)C16—O5—C20—C21−169.8 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1W—H1WA···O10.852.513.182 (5)137
O1W—H1WA···O40.852.152.936 (5)154
O1W—H1WB···O20.852.212.883 (5)136
O1W—H1WB···O50.852.182.952 (5)151
O7A—H7A···O1W0.822.102.899 (19)164
C8—H8C···O30.972.312.829 (5)113

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: JH2132).

References

  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
  • Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl.34, 1555–1573.
  • Blower, P. J. (1998). Transition Met. Chem.23, 109–112.
  • Bruker (2005). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Elmali, A., Elerman, Y. & Svoboda, I. (2000). Acta Cryst. C56, 423–424. [PubMed]
  • Granovski, A. D., Nivorozhkin, A. L. & Minkin, V. I. (1993). Coord. Chem. Rev.126, 1–69.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]

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