Literature DB >> 21582391

Bis(2-hydroxy-N'-isopropylidenebenzo-hydrazidato-κN',O)bis-(pyridine-κN)cobalt(II).

Xiaojuan Zhao1, Dacheng Li, Yupeng Pan.   

Abstract

In the title complex, [Co(C(10)H(11)N(2)O(2))(2)(C(5)H(5)N)(2)], the Co(II) atom lies on a centre of symmetry and adopts a distorted cis-CoO(2)N(4) octa-hedral geometry. The two acetone salicyloylhydrazone ligands are deprotonated and act as N,O-bidentate monoanionic ligands, forming the equatorial plane, while the axial positions are occupied by two N atoms of two pyridine mol-ecules. The complex presents O-H⋯N and C-H⋯N intra-molecular hydrogen bonds. Inter-molecular C-H⋯N and C-H⋯O inter-actions are also present in the crystal.

Entities:  

Year:  2009        PMID： 21582391      PMCID： PMC2968839          DOI： 10.1107/S1600536809011015

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For the crystal structure of acetone salicylhydrazone, see: Kraudelt et al. (1996 ▶). For the crystal structure of iron and nickel complexes with related aroylhydrazone derivatives, see: Matoga et al. (2007 ▶) and Liu et al. (2005 ▶), respectively. For the biological activity of aroylhydrazones, see: Armstrong et al. (2003 ▶). For the crystal structure of 3-hydr­oxy-N-[phen­yl(2-pyrid­yl)methyl­ene]-2-naphthohydrazide, see: Kang et al. (2007 ▶).

Experimental

Crystal data

[Co(C10H11N2O2)2(C5H5N)2] M = 599.55 Monoclinic, a = 7.7751 (9) Å b = 10.0168 (15) Å c = 18.751 (2) Å β = 96.621 (2)° V = 1450.6 (3) Å3 Z = 2 Mo Kα radiation μ = 0.64 mm−1 T = 298 K 0.34 × 0.19 × 0.16 mm

Data collection

Siemens SMART CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.813, T max = 0.905 7087 measured reflections 2547 independent reflections 1675 reflections with I > 2σ(I) R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.041 wR(F 2) = 0.106 S = 1.00 2547 reflections 187 parameters H-atom parameters constrained Δρmax = 0.30 e Å−3 Δρmin = −0.24 e Å−3 Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL. Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809011015/bg2240sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809011015/bg2240Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Co(C10H11N2O2)2(C5H5N)2]F(000) = 626
Mr = 599.55Dx = 1.373 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1792 reflections
a = 7.7751 (9) Åθ = 2.3–21.6°
b = 10.0168 (15) ŵ = 0.64 mm−1
c = 18.751 (2) ÅT = 298 K
β = 96.621 (2)°Block, brown
V = 1450.6 (3) Å30.34 × 0.19 × 0.16 mm
Z = 2
Siemens SMART CCD area-detector diffractometer2547 independent reflections
Radiation source: fine-focus sealed tube1675 reflections with I > 2σ(I)
graphiteRint = 0.039
φ and ω scansθmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −9→9
Tmin = 0.813, Tmax = 0.905k = −11→11
7087 measured reflectionsl = −11→22
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106H-atom parameters constrained
S = 1.00w = 1/[σ2(Fo2) + (0.046P)2 + 0.3767P] where P = (Fo2 + 2Fc2)/3
2547 reflections(Δ/σ)max < 0.001
187 parametersΔρmax = 0.30 e Å−3
0 restraintsΔρmin = −0.23 e Å−3
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.
xyzUiso*/Ueq
Co10.00000.50000.00000.0385 (2)
N10.0380 (3)0.7734 (2)0.06265 (13)0.0414 (6)
N20.1297 (3)0.6915 (2)0.01957 (13)0.0423 (6)
N30.1601 (3)0.4115 (2)0.09485 (13)0.0437 (6)
O1−0.1480 (2)0.59481 (19)0.06648 (11)0.0461 (5)
O2−0.0353 (3)0.9926 (2)0.11969 (14)0.0671 (7)
H20.01620.94150.09540.101*
C1−0.1001 (4)0.7132 (3)0.08301 (15)0.0386 (7)
C2−0.2036 (4)0.7937 (3)0.12879 (16)0.0413 (7)
C3−0.1665 (5)0.9282 (3)0.14443 (18)0.0517 (9)
C4−0.2665 (5)0.9984 (4)0.1888 (2)0.0663 (10)
H4−0.24361.08810.19850.080*
C5−0.3972 (6)0.9365 (4)0.2178 (2)0.0767 (12)
H5−0.46190.98410.24790.092*
C6−0.4357 (5)0.8035 (4)0.2032 (2)0.0748 (11)
H6−0.52540.76150.22330.090*
C7−0.3389 (4)0.7348 (3)0.15852 (18)0.0564 (9)
H7−0.36550.64590.14800.068*
C80.2667 (4)0.7445 (3)0.00010 (18)0.0499 (8)
C90.3747 (5)0.6670 (4)−0.0454 (2)0.0804 (12)
H9A0.32730.5790−0.05300.121*
H9B0.49070.6608−0.02180.121*
H9C0.37600.7111−0.09080.121*
C100.3260 (5)0.8822 (3)0.0211 (2)0.0697 (11)
H10A0.24580.9461−0.00180.105*
H10B0.43860.89720.00640.105*
H10C0.33170.89180.07230.105*
C110.2490 (4)0.4881 (3)0.14411 (17)0.0553 (9)
H110.24100.58030.13880.066*
C120.3514 (4)0.4381 (4)0.20208 (19)0.0621 (10)
H120.41030.49570.23530.074*
C130.3666 (4)0.3029 (3)0.21092 (19)0.0620 (10)
H130.43650.26690.24980.074*
C140.2763 (4)0.2223 (3)0.16120 (18)0.0593 (9)
H140.28330.12990.16550.071*
C150.1749 (4)0.2803 (3)0.10463 (18)0.0520 (9)
H150.11310.22450.07130.062*
U11U22U33U12U13U23
Co10.0379 (3)0.0375 (3)0.0410 (4)−0.0085 (3)0.0080 (2)−0.0035 (3)
N10.0431 (15)0.0393 (13)0.0413 (15)−0.0086 (12)0.0032 (12)−0.0028 (13)
N20.0413 (15)0.0419 (14)0.0440 (15)−0.0102 (12)0.0055 (12)−0.0017 (12)
N30.0434 (15)0.0448 (15)0.0427 (16)−0.0065 (12)0.0039 (12)0.0008 (13)
O10.0472 (12)0.0390 (12)0.0549 (14)−0.0114 (10)0.0177 (10)−0.0065 (11)
O20.0715 (16)0.0431 (13)0.0864 (18)−0.0074 (12)0.0079 (14)−0.0139 (13)
C10.0430 (18)0.0383 (17)0.0333 (17)−0.0019 (14)−0.0011 (14)0.0028 (14)
C20.0469 (18)0.0400 (17)0.0357 (17)0.0033 (14)−0.0002 (14)−0.0022 (15)
C30.057 (2)0.049 (2)0.046 (2)0.0038 (17)−0.0061 (17)−0.0022 (17)
C40.081 (3)0.052 (2)0.064 (2)0.016 (2)0.000 (2)−0.017 (2)
C50.086 (3)0.086 (3)0.060 (3)0.034 (3)0.016 (2)−0.009 (2)
C60.081 (3)0.070 (3)0.079 (3)0.015 (2)0.035 (2)0.005 (2)
C70.063 (2)0.050 (2)0.059 (2)0.0054 (17)0.0165 (18)0.0016 (18)
C80.0446 (19)0.051 (2)0.054 (2)−0.0164 (16)0.0066 (16)0.0036 (17)
C90.064 (2)0.077 (3)0.106 (3)−0.024 (2)0.035 (2)−0.010 (3)
C100.064 (2)0.057 (2)0.089 (3)−0.0276 (18)0.011 (2)0.001 (2)
C110.061 (2)0.0479 (19)0.053 (2)−0.0063 (17)−0.0081 (17)−0.0033 (19)
C120.067 (2)0.064 (2)0.051 (2)−0.0071 (19)−0.0117 (19)−0.0052 (19)
C130.065 (2)0.066 (2)0.052 (2)−0.0037 (19)−0.0074 (18)0.009 (2)
C140.065 (2)0.050 (2)0.061 (2)−0.0064 (17)−0.0011 (19)0.0112 (19)
C150.057 (2)0.048 (2)0.050 (2)−0.0099 (16)−0.0015 (17)−0.0015 (17)
Co1—O12.028 (2)C5—H50.9300
Co1—O1i2.028 (2)C6—C71.374 (5)
Co1—N2i2.179 (2)C6—H60.9300
Co1—N22.179 (2)C7—H70.9300
Co1—N32.233 (2)C8—C91.483 (5)
Co1—N3i2.233 (2)C8—C101.492 (4)
N1—C11.326 (3)C9—H9A0.9600
N1—N21.403 (3)C9—H9B0.9600
N2—C81.280 (4)C9—H9C0.9600
N3—C151.330 (4)C10—H10A0.9600
N3—C111.332 (3)C10—H10B0.9600
O1—C11.270 (3)C10—H10C0.9600
O2—C31.335 (4)C11—C121.366 (4)
O2—H20.8200C11—H110.9300
C1—C21.481 (4)C12—C131.368 (5)
C2—C71.379 (4)C12—H120.9300
C2—C31.402 (4)C13—C141.365 (4)
C3—C41.392 (5)C13—H130.9300
C4—C51.357 (5)C14—C151.375 (4)
C4—H40.9300C14—H140.9300
C5—C61.386 (5)C15—H150.9300
O1—Co1—O1i180.00 (9)C6—C5—H5119.5
O1—Co1—N2i103.38 (8)C7—C6—C5118.7 (4)
O1i—Co1—N2i76.62 (8)C7—C6—H6120.6
O1—Co1—N276.62 (8)C5—C6—H6120.6
O1i—Co1—N2103.38 (8)C6—C7—C2122.0 (3)
N2i—Co1—N2180.00 (13)C6—C7—H7119.0
O1—Co1—N390.00 (9)C2—C7—H7119.0
O1i—Co1—N390.00 (9)N2—C8—C9119.4 (3)
N2i—Co1—N389.38 (9)N2—C8—C10123.4 (3)
N2—Co1—N390.62 (9)C9—C8—C10117.2 (3)
O1—Co1—N3i90.00 (9)C8—C9—H9A109.5
O1i—Co1—N3i90.00 (9)C8—C9—H9B109.5
N2i—Co1—N3i90.62 (9)H9A—C9—H9B109.5
N2—Co1—N3i89.38 (9)C8—C9—H9C109.5
N3—Co1—N3i180.0H9A—C9—H9C109.5
C1—N1—N2112.5 (2)H9B—C9—H9C109.5
C8—N2—N1114.6 (2)C8—C10—H10A109.5
C8—N2—Co1134.5 (2)C8—C10—H10B109.5
N1—N2—Co1110.84 (16)H10A—C10—H10B109.5
C15—N3—C11116.4 (3)C8—C10—H10C109.5
C15—N3—Co1122.3 (2)H10A—C10—H10C109.5
C11—N3—Co1121.4 (2)H10B—C10—H10C109.5
C1—O1—Co1114.58 (18)N3—C11—C12123.3 (3)
C3—O2—H2109.5N3—C11—H11118.4
O1—C1—N1125.4 (3)C12—C11—H11118.4
O1—C1—C2119.1 (3)C11—C12—C13119.6 (3)
N1—C1—C2115.5 (3)C11—C12—H12120.2
C7—C2—C3118.3 (3)C13—C12—H12120.2
C7—C2—C1119.5 (3)C14—C13—C12118.2 (3)
C3—C2—C1122.2 (3)C14—C13—H13120.9
O2—C3—C4117.8 (3)C12—C13—H13120.9
O2—C3—C2122.6 (3)C13—C14—C15118.7 (3)
C4—C3—C2119.6 (4)C13—C14—H14120.6
C5—C4—C3120.3 (4)C15—C14—H14120.6
C5—C4—H4119.8N3—C15—C14123.8 (3)
C3—C4—H4119.8N3—C15—H15118.1
C4—C5—C6121.0 (4)C14—C15—H15118.1
C4—C5—H5119.5
C1—N1—N2—C8−178.4 (3)N1—C1—C2—C7−173.4 (3)
C1—N1—N2—Co12.4 (3)O1—C1—C2—C3−174.8 (3)
O1—Co1—N2—C8178.1 (3)N1—C1—C2—C35.3 (4)
O1i—Co1—N2—C8−1.9 (3)C7—C2—C3—O2178.2 (3)
N3—Co1—N2—C888.3 (3)C1—C2—C3—O2−0.5 (5)
N3i—Co1—N2—C8−91.7 (3)C7—C2—C3—C4−0.3 (5)
O1—Co1—N2—N1−2.81 (16)C1—C2—C3—C4−179.0 (3)
O1i—Co1—N2—N1177.19 (16)O2—C3—C4—C5−177.3 (3)
N3—Co1—N2—N1−92.66 (17)C2—C3—C4—C51.2 (5)
N3i—Co1—N2—N187.34 (17)C3—C4—C5—C6−1.0 (6)
O1—Co1—N3—C15120.1 (2)C4—C5—C6—C7−0.1 (6)
O1i—Co1—N3—C15−59.9 (2)C5—C6—C7—C21.0 (6)
N2i—Co1—N3—C1516.7 (2)C3—C2—C7—C6−0.8 (5)
N2—Co1—N3—C15−163.3 (2)C1—C2—C7—C6177.9 (3)
O1—Co1—N3—C11−61.3 (2)N1—N2—C8—C9179.7 (3)
O1i—Co1—N3—C11118.7 (2)Co1—N2—C8—C9−1.2 (5)
N2i—Co1—N3—C11−164.6 (2)N1—N2—C8—C100.0 (4)
N2—Co1—N3—C1115.4 (2)Co1—N2—C8—C10179.1 (2)
N2i—Co1—O1—C1−177.13 (19)C15—N3—C11—C120.1 (5)
N2—Co1—O1—C12.87 (19)Co1—N3—C11—C12−178.6 (3)
N3—Co1—O1—C193.5 (2)N3—C11—C12—C130.5 (6)
N3i—Co1—O1—C1−86.5 (2)C11—C12—C13—C14−0.6 (6)
Co1—O1—C1—N1−2.7 (4)C12—C13—C14—C150.1 (5)
Co1—O1—C1—C2177.38 (18)C11—N3—C15—C14−0.7 (5)
N2—N1—C1—O10.0 (4)Co1—N3—C15—C14178.0 (3)
N2—N1—C1—C2180.0 (2)C13—C14—C15—N30.6 (5)
O1—C1—C2—C76.5 (4)
D—H···AD—HH···AD···AD—H···A
O2—H2···N10.821.812.536 (3)147
C7—H7···O10.932.462.782 (4)100
C11—H11···N20.932.563.157 (4)123
C9—H9A···O1i0.962.233.159 (4)164
C15—H15···N2i0.932.543.137 (4)123
Table 1

Selected bond lengths (Å)

Co1—O12.028 (2)
Co1—O1i2.028 (2)
Co1—N2i2.179 (2)
Co1—N22.179 (2)
Co1—N32.233 (2)
Co1—N3i2.233 (2)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
O2—H2⋯N10.821.812.536 (3)147
C11—H11⋯N20.932.563.157 (4)123
C9—H9A⋯O1i0.962.233.159 (4)164
C15—H15⋯N2i0.932.543.137 (4)123

Symmetry code: (i) .

  2 in total

1.  Iron(III) complexes with a biologically relevant aroylhydrazone: crystallographic evidence for coordination versatility.

Authors:  Dariusz Matoga; Janusz Szklarzewicz; Katarzyna Stadnicka; Musa S Shongwe
Journal:  Inorg Chem       Date:  2007-09-25       Impact factor: 5.165

2.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290
  2 in total

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