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Acta Crystallogr Sect E Struct Rep Online. 2009 July 1; 65(Pt 7): m770.
Published online 2009 June 13. doi:  10.1107/S1600536809021540
PMCID: PMC2969264

{2,2′-[6,6′-Dimethoxy­cyclo­hexane-1,2-diylbis(nitrilo­methyl­idyne)]diphenolato-κ4 O 1,N,N′,O 1′}cobalt(II) monohydrate

Abstract

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 π–π ring inter­actions may be present between symmetry-related complexes, with centroid–centroid distances of 3.5661 (8) Å.

Related literature

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

An external file that holds a picture, illustration, etc.
Object name is e-65-0m770-scheme1.jpg

Experimental

Crystal data

  • [Co(C22H24N2O4)]·H2O
  • M r = 457.38
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m770-efi1.jpg
  • a = 11.241 (3) Å
  • b = 10.605 (3) Å
  • c = 17.864 (7) Å
  • β = 107.158 (14)°
  • V = 2034.9 (12) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.88 mm−1
  • T = 291 K
  • 0.20 × 0.19 × 0.17 mm

Data collection

  • Rigaku R-AXIS RAPID diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.826, T max = 0.851
  • 19221 measured reflections
  • 4647 independent reflections
  • 3840 reflections with I > 2σ(I)
  • R int = 0.034

Refinement

  • R[F 2 > 2σ(F 2)] = 0.029
  • wR(F 2) = 0.069
  • S = 1.04
  • 4647 reflections
  • 373 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.36 e Å−3
  • Δρmin = −0.24 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 [triangle]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809021540/cs2106sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809021540/cs2106Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Comment

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.

Experimental

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

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

Figures

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.
Fig. 2.
Heteroatomic π–π ring interactions across an inversion center, indicated by broken lines.

Crystal data

[Co(C22H24N2O4)]·H2OF(000) = 956
Mr = 457.38Dx = 1.493 Mg m3
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 mm1
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

Rigaku R-AXIS RAPID diffractometer4647 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

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 = 1.04w = 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 Å3
0 restraintsΔρmin = −0.24 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

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)

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, °)

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, °)

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)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CS2106).

References

  • Higashi, T. (1995). ABSCOR Rigaku Corporation, Tokyo, Japan.
  • Lu, X. P., Wong, W. Y. & Wong, W. K. (2008). J. Eur. Inorg. Chem. pp. 523-–528.
  • Rigaku (1998). RAPID-AUTO Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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