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Acta Cryst. (2009). E65, m770    [ doi:10.1107/S1600536809021540 ]

{2,2'-[6,6'-Dimethoxycyclohexane-1,2-diylbis(nitrilomethylidyne)]diphenolato-[kappa]4O1,N,N',O1'}cobalt(II) monohydrate

Y. Bao, H.-F. Li, P.-F. Yan, G.-M. Li and G.-F. Hou

Abstract top

In the title complex, [Co(C22H24N2O4)]·H2O, the CoII atom is in an almost square-planar coordination environment involving two O and two N atoms from the Schiff base ligand. A water molecule cocrystallizes with the coordination compound and may be held in the crystal by O-H...O hydrogen bonds. Heteroatomic [pi]-[pi] ring interactions may be present between symmetry-related complexes, with centroid-centroid distances of 3.5661 (8) Å.

Comment top

As shown in Fig. 1, CoII is four-coordinated in a square planar environment as the ligating Schiff base is a tetradentate ligand (Table 1). The co-crystallized water molecule does not coordinate to the Co ion. Its position is stabilized by bifurcated O—H···O hydrogen bonds (Table 2). It is also worth noting that stabilizing π–π ring interactions may occur between symmetry center related phenyl C1 -> C6 and C7 -> O1 heteroatomic rings, as show in Fig. 2. The π–π center to center distance is 3.5661 (8) Å. Together with an almost perfect rings-to-rings matching this may indicate appreciable interactions.

Related literature top

For related platinum complexes of a similar Schiff base, see: Lu et al. (2008).

Experimental top

The title complex was obtained by the treatment of cobalt(II) acetate tetrahydrate with the neutral Schiff base in methanol/acetone (1:2). The yellow clear mixture turned to salmon pink precipitation after stirred for 4 h; diethyl ether was allowed to diffuse slowly into the solution of the filtrate. Red single crystals were obtained after several days.Analysis calculated for C22H26CoN2O5: C, 57.77; H, 5.73; N, 6.12; Co, 12.88; found: C, 57.56; H, 5.23; N, 6.77; Co, 12.79%.

Refinement top

All H atoms were located in difference Fourier maps and freely refined, but water H atoms was set Uiso(H) = 1.5Ueq(O).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: RAPID-AUTO (Rigaku, 1998); 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: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title complex, showing 30% probability displacement ellipsoids for non-H atoms. Dashed lines indicate the hydrogen-bonding interactions between the water and the host.
[Figure 2] Fig. 2. Heteroatomic π–π ring interactions across an inversion center, indicated by broken lines.
{2,2'-[6,6'-Dimethoxycyclohexane-1,2-diylbis(nitrilomethylidyne)]diphenolato- κ4O1,N,N',O1'}cobalt(II) monohydrate top
Crystal data top
[Co(C22H24N2O4)]·H2OF(000) = 956
Mr = 457.38Dx = 1.493 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 15295 reflections
a = 11.241 (3) Åθ = 3.1–27.5°
b = 10.605 (3) ŵ = 0.88 mm−1
c = 17.864 (7) ÅT = 291 K
β = 107.158 (14)°Block, red
V = 2034.9 (12) Å30.20 × 0.19 × 0.17 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID
diffractometer		4647 independent reflections
Radiation source: fine-focus sealed tube3840 reflections with I > 2σ(I)
graphiteRint = 0.034
ω scansθmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		h = −14→14
Tmin = 0.826, Tmax = 0.851k = −11→13
19221 measured reflectionsl = −23→23
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.029Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.069H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0317P)2 + 0.4P]
where P = (Fo2 + 2Fc2)/3
4647 reflections(Δ/σ)max = 0.001
373 parametersΔρmax = 0.36 e Å−3
0 restraintsΔρmin = −0.24 e Å−3
Crystal data top
[Co(C22H24N2O4)]·H2OV = 2034.9 (12) Å3
Mr = 457.38Z = 4
Monoclinic, P21/nMo Kα radiation
a = 11.241 (3) ŵ = 0.88 mm−1
b = 10.605 (3) ÅT = 291 K
c = 17.864 (7) Å0.20 × 0.19 × 0.17 mm
β = 107.158 (14)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer		4647 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		3840 reflections with I > 2σ(I)
Tmin = 0.826, Tmax = 0.851Rint = 0.034
19221 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.029H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.069Δρmax = 0.36 e Å−3
S = 1.04Δρmin = −0.24 e Å−3
4647 reflectionsAbsolute structure: ?
373 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.55207 (14)0.17711 (15)0.02619 (9)0.0336 (3)
C20.47583 (15)0.27964 (16)−0.01173 (10)0.0397 (4)
C30.46233 (17)0.30829 (18)−0.08877 (11)0.0450 (4)
C40.52295 (17)0.23721 (19)−0.13239 (11)0.0476 (4)
C50.59830 (16)0.13964 (19)−0.09779 (10)0.0427 (4)
C60.61536 (14)0.10945 (15)−0.01824 (9)0.0336 (3)
C70.69932 (14)0.00941 (16)0.01550 (10)0.0346 (3)
C80.81705 (14)−0.13254 (16)0.11525 (10)0.0349 (3)
C90.91820 (16)−0.1510 (2)0.07467 (11)0.0448 (4)
C101.01669 (18)−0.0482 (2)0.09542 (13)0.0548 (5)
C111.07198 (18)−0.0338 (3)0.18328 (13)0.0588 (6)
C120.97012 (17)−0.0087 (2)0.22218 (12)0.0462 (4)
C130.87250 (15)−0.11292 (17)0.20283 (10)0.0364 (4)
C140.75527 (16)−0.12574 (16)0.29443 (10)0.0385 (4)
C150.65495 (15)−0.09883 (17)0.32630 (10)0.0386 (4)
C160.6452 (2)−0.1711 (2)0.39057 (12)0.0509 (5)
C170.5519 (2)−0.1499 (2)0.42283 (13)0.0629 (6)
C180.4652 (2)−0.0550 (2)0.39271 (13)0.0602 (6)
C190.47299 (17)0.01755 (19)0.33093 (11)0.0447 (4)
C200.56884 (15)−0.00204 (16)0.29425 (10)0.0365 (4)
C210.2944 (2)0.1401 (3)0.33174 (16)0.0633 (6)
C220.3317 (2)0.4392 (2)0.00145 (17)0.0610 (6)
N10.73023 (11)−0.02450 (13)0.08792 (8)0.0322 (3)
N20.76520 (12)−0.07817 (13)0.23028 (8)0.0351 (3)
Co10.656300 (17)0.030194 (19)0.162807 (12)0.02751 (7)
O10.55821 (10)0.15217 (11)0.09913 (7)0.0371 (3)
O20.42054 (14)0.34365 (13)0.03579 (9)0.0586 (4)
O30.57104 (11)0.06922 (11)0.23491 (7)0.0400 (3)
O40.39176 (12)0.11321 (15)0.29806 (8)0.0559 (4)
O50.30979 (18)0.1993 (3)0.13719 (12)0.0994 (7)
H250.370 (4)0.239 (4)0.122 (2)0.149*
H260.354 (4)0.176 (4)0.185 (2)0.149*
H50.7650 (15)−0.2112 (17)0.1078 (10)0.034 (4)*
H40.7370 (17)−0.0353 (16)−0.0216 (11)0.042 (5)*
H150.8198 (16)−0.1865 (17)0.3229 (10)0.038 (5)*
H140.9086 (16)−0.1919 (17)0.2269 (11)0.039 (5)*
H60.8798 (17)−0.1612 (17)0.0162 (12)0.047 (5)*
H10.4088 (17)0.3782 (18)−0.1147 (11)0.047 (5)*
H130.9278 (18)0.077 (2)0.2029 (12)0.053 (6)*
H121.0042 (19)−0.0036 (18)0.2804 (13)0.051 (6)*
H20.5101 (18)0.2573 (19)−0.1860 (13)0.057 (6)*
H230.261 (2)0.402 (2)−0.0407 (14)0.062 (6)*
H160.704 (2)−0.237 (2)0.4099 (13)0.060 (6)*
H30.6401 (19)0.087 (2)−0.1280 (12)0.058 (6)*
H70.9564 (18)−0.235 (2)0.0946 (12)0.054 (6)*
H90.978 (2)0.038 (2)0.0714 (14)0.065 (7)*
H190.329 (2)0.168 (2)0.3868 (16)0.077 (7)*
H180.396 (2)−0.039 (2)0.4151 (15)0.079 (8)*
H111.132 (2)0.044 (2)0.1943 (14)0.071 (7)*
H170.541 (2)−0.207 (2)0.4636 (15)0.078 (7)*
H200.247 (2)0.060 (2)0.3337 (14)0.068 (7)*
H220.301 (2)0.471 (2)0.0463 (17)0.087 (9)*
H81.082 (2)−0.065 (2)0.0701 (13)0.063 (6)*
H101.116 (2)−0.111 (2)0.2077 (14)0.064 (7)*
H240.368 (2)0.504 (3)−0.0252 (16)0.087 (9)*
H210.245 (2)0.210 (2)0.2927 (16)0.083 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0289 (7)0.0366 (8)0.0335 (9)−0.0053 (6)0.0065 (6)0.0020 (7)
C20.0366 (8)0.0387 (9)0.0430 (10)−0.0011 (7)0.0104 (7)0.0043 (8)
C30.0400 (9)0.0438 (10)0.0466 (11)−0.0021 (8)0.0054 (8)0.0121 (8)
C40.0482 (10)0.0565 (12)0.0349 (10)−0.0083 (9)0.0072 (8)0.0100 (9)
C50.0422 (9)0.0514 (11)0.0341 (9)−0.0054 (8)0.0105 (8)−0.0002 (8)
C60.0292 (7)0.0386 (9)0.0319 (8)−0.0049 (7)0.0074 (6)0.0008 (7)
C70.0323 (7)0.0409 (9)0.0315 (8)−0.0029 (7)0.0110 (7)−0.0045 (7)
C80.0307 (7)0.0358 (9)0.0381 (9)0.0020 (7)0.0099 (7)−0.0035 (7)
C90.0385 (9)0.0572 (12)0.0393 (10)0.0107 (8)0.0125 (8)−0.0032 (9)
C100.0384 (9)0.0813 (16)0.0489 (12)−0.0047 (10)0.0194 (9)0.0004 (11)
C110.0355 (9)0.0888 (17)0.0521 (13)−0.0097 (11)0.0130 (9)−0.0079 (12)
C120.0381 (9)0.0593 (12)0.0386 (10)−0.0060 (8)0.0075 (8)−0.0066 (9)
C130.0319 (8)0.0415 (9)0.0360 (9)0.0060 (7)0.0105 (7)0.0040 (7)
C140.0409 (9)0.0395 (9)0.0337 (9)0.0009 (7)0.0092 (7)0.0034 (7)
C150.0404 (8)0.0454 (10)0.0303 (8)−0.0045 (8)0.0111 (7)−0.0004 (7)
C160.0575 (11)0.0561 (12)0.0401 (11)−0.0021 (10)0.0162 (9)0.0087 (9)
C170.0711 (14)0.0784 (16)0.0467 (12)−0.0038 (12)0.0292 (11)0.0157 (11)
C180.0566 (12)0.0860 (17)0.0480 (12)−0.0035 (11)0.0309 (10)0.0033 (11)
C190.0411 (9)0.0589 (11)0.0367 (9)−0.0019 (8)0.0157 (8)−0.0045 (8)
C200.0385 (8)0.0438 (9)0.0280 (8)−0.0046 (7)0.0109 (7)−0.0039 (7)
C210.0442 (11)0.0938 (19)0.0601 (15)−0.0018 (13)0.0281 (11)−0.0154 (14)
C220.0524 (12)0.0483 (12)0.0757 (17)0.0146 (10)0.0088 (12)0.0001 (12)
N10.0286 (6)0.0357 (7)0.0324 (7)−0.0002 (6)0.0091 (5)−0.0018 (6)
N20.0345 (7)0.0380 (7)0.0335 (7)0.0013 (6)0.0112 (6)0.0013 (6)
Co10.02730 (10)0.03082 (12)0.02579 (11)0.00243 (8)0.00995 (8)0.00088 (8)
O10.0373 (6)0.0411 (6)0.0344 (6)0.0063 (5)0.0128 (5)0.0035 (5)
O20.0652 (8)0.0561 (8)0.0584 (9)0.0267 (7)0.0244 (7)0.0140 (7)
O30.0448 (6)0.0445 (7)0.0350 (6)0.0063 (5)0.0186 (5)0.0036 (5)
O40.0476 (7)0.0772 (10)0.0513 (8)0.0127 (7)0.0277 (6)0.0003 (7)
O50.0700 (12)0.161 (2)0.0736 (13)0.0206 (13)0.0315 (10)0.0263 (14)
Geometric parameters (Å, °) top
C1—O11.3112 (19)C13—N21.477 (2)
C1—C61.409 (2)C13—H140.974 (18)
C1—C21.426 (2)C14—N21.287 (2)
C2—O21.371 (2)C14—C151.434 (2)
C2—C31.373 (3)C14—H150.991 (18)
C3—C41.398 (3)C15—C201.411 (2)
C3—H10.980 (19)C15—C161.411 (2)
C4—C51.364 (3)C16—C171.356 (3)
C4—H20.95 (2)C16—H160.96 (2)
C5—C61.413 (2)C17—C181.394 (3)
C5—H30.99 (2)C17—H170.98 (2)
C6—C71.430 (2)C18—C191.369 (3)
C7—N11.288 (2)C18—H180.99 (3)
C7—H41.005 (19)C19—O41.375 (2)
C8—N11.491 (2)C19—C201.432 (2)
C8—C131.518 (2)C20—O31.308 (2)
C8—C91.531 (2)C21—O41.425 (2)
C8—H51.005 (17)C21—H190.99 (3)
C9—C101.519 (3)C21—H201.01 (2)
C9—H61.01 (2)C21—H211.06 (3)
C9—H71.01 (2)C22—O21.427 (2)
C10—C111.516 (3)C22—H231.00 (2)
C10—H91.05 (2)C22—H221.02 (3)
C10—H80.98 (2)C22—H240.99 (3)
C11—C121.528 (3)N1—Co11.8635 (14)
C11—H111.04 (2)N2—Co11.8443 (14)
C11—H100.99 (2)Co1—O11.8556 (12)
C12—C131.524 (3)Co1—O31.8647 (12)
C12—H131.04 (2)O5—H250.90 (4)
C12—H121.00 (2)O5—H260.89 (4)
O1—C1—C6124.74 (15)N2—C13—H14110.1 (10)
O1—C1—C2118.30 (15)C8—C13—H14109.1 (11)
C6—C1—C2116.96 (15)C12—C13—H14110.2 (10)
O2—C2—C3125.08 (16)N2—C14—C15124.09 (16)
O2—C2—C1113.72 (15)N2—C14—H15118.0 (10)
C3—C2—C1121.20 (16)C15—C14—H15117.9 (10)
C2—C3—C4120.77 (17)C20—C15—C16121.09 (16)
C2—C3—H1120.7 (11)C20—C15—C14120.62 (15)
C4—C3—H1118.5 (11)C16—C15—C14118.29 (17)
C5—C4—C3119.74 (18)C17—C16—C15120.7 (2)
C5—C4—H2121.1 (12)C17—C16—H16120.3 (13)
C3—C4—H2119.2 (12)C15—C16—H16118.9 (13)
C4—C5—C6120.62 (17)C16—C17—C18119.7 (2)
C4—C5—H3121.0 (12)C16—C17—H17119.7 (14)
C6—C5—H3118.3 (12)C18—C17—H17120.3 (14)
C1—C6—C5120.65 (16)C19—C18—C17120.92 (18)
C1—C6—C7121.38 (15)C19—C18—H18118.5 (15)
C5—C6—C7117.96 (15)C17—C18—H18120.6 (14)
N1—C7—C6125.43 (15)C18—C19—O4124.51 (17)
N1—C7—H4119.3 (11)C18—C19—C20121.53 (19)
C6—C7—H4115.2 (11)O4—C19—C20113.96 (16)
N1—C8—C13105.21 (13)O3—C20—C15125.06 (14)
N1—C8—C9116.68 (14)O3—C20—C19118.93 (16)
C13—C8—C9111.66 (14)C15—C20—C19116.01 (15)
N1—C8—H5107.2 (9)O4—C21—H19110.8 (14)
C13—C8—H5107.2 (10)O4—C21—H20108.8 (13)
C9—C8—H5108.5 (9)H19—C21—H20105.9 (19)
C10—C9—C8112.49 (16)O4—C21—H21100.6 (14)
C10—C9—H6112.8 (11)H19—C21—H21115 (2)
C8—C9—H6110.6 (10)H20—C21—H21115.9 (19)
C10—C9—H7110.1 (11)O2—C22—H23109.8 (13)
C8—C9—H7104.1 (11)O2—C22—H22104.5 (15)
H6—C9—H7106.1 (16)H23—C22—H22110.4 (19)
C11—C10—C9111.82 (18)O2—C22—H24111.5 (15)
C11—C10—H9109.3 (13)H23—C22—H24105 (2)
C9—C10—H9110.1 (12)H22—C22—H24116 (2)
C11—C10—H8111.3 (13)C7—N1—C8120.01 (13)
C9—C10—H8110.0 (13)C7—N1—Co1126.08 (11)
H9—C10—H8104.2 (17)C8—N1—Co1113.06 (10)
C10—C11—C12110.80 (17)C14—N2—C13119.46 (14)
C10—C11—H11108.6 (13)C14—N2—Co1127.67 (12)
C12—C11—H11108.0 (13)C13—N2—Co1112.85 (11)
C10—C11—H10111.9 (14)N2—Co1—O1174.19 (6)
C12—C11—H10106.9 (13)N2—Co1—N185.67 (6)
H11—C11—H10110.6 (18)O1—Co1—N195.00 (6)
C13—C12—C11110.88 (17)N2—Co1—O393.68 (6)
C13—C12—H13109.3 (11)O1—Co1—O386.28 (5)
C11—C12—H13109.5 (11)N1—Co1—O3173.66 (5)
C13—C12—H12107.7 (11)C1—O1—Co1126.68 (10)
C11—C12—H12112.0 (12)C2—O2—C22118.21 (17)
H13—C12—H12107.3 (16)C20—O3—Co1124.61 (11)
N2—C13—C8104.42 (13)C19—O4—C21117.60 (18)
N2—C13—C12110.35 (14)H25—O5—H2699 (3)
C8—C13—C12112.49 (15)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O5—H25···O20.90 (4)2.11 (4)2.916 (3)149 (3)
O5—H25···O10.90 (4)2.45 (4)3.103 (2)129 (3)
O5—H26···O40.89 (4)2.05 (4)2.895 (3)159 (4)
O5—H26···O30.89 (4)2.59 (4)3.248 (2)131 (3)
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O5—H25···O20.90 (4)2.11 (4)2.916 (3)149 (3)
O5—H25···O10.90 (4)2.45 (4)3.103 (2)129 (3)
O5—H26···O40.89 (4)2.05 (4)2.895 (3)159 (4)
O5—H26···O30.89 (4)2.59 (4)3.248 (2)131 (3)
Acknowledgements top

The authors gratefully acknowledge financial support from the National Natural Science Foundation of China (Nos. 20572018 and 20672032), Heilongjiang Province (Nos. 1055HZ001, ZJG0504 and JC200605) and Heilongjiang University.

references
References top

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Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.