supplementary materials


xu2418 scheme

Acta Cryst. (2008). E64, m795    [ doi:10.1107/S1600536808013135 ]

(Aminoacetato-[kappa]2O,N)bis(quinolin-8-olato-[kappa]2O,N)cobalt(III) methanol solvate

B.-Q. Jing, S.-M. Meng, J. Han, B. Wang and X.-M. Li

Abstract top

In the crystal structure of the title compound, [Co(C2H4NO2)(C9H6NO)2]·CH3OH, the CoIII atom is chelated by two quinolin-8-olate and one glycinate anions in a distorted octahedral coordination geometry. The five-membered chelating glycinate ring assumes an envelope conformation. The complex molecules are assembled by intermolecular N-H...O hydrogen bonding.

Comment top

The 8–hydroxyquinoline (HQ) is a very good ligand, forms complex compounds with various metal ions in solution. The strong chelating action of HQ in solution has been extensively studied and widely used in analytical chemistry. In this work, we use glycin and 8–hydroxyquinoline as bidedtate ligand to synthesize the title complex, (I).

The molecular structure of the title compound is shown in Fig. 1. The CoIII atom is chelated by two 8-hydroxyquinoline and one glycin anions in a distorted octahedral coordination geometry. The Co—N bond distances are longer than Co—O bond distances (Table 1), which agrees with that found in a related structure, tris(8-quinolinolato)-cobalt(III) methanol solvate (Li et al. 2003). The two 8-hydroxyquinolate rings are almost perpendicular to each other with a dihedral angle of 81.0°. The five-membered chelating ring of the glycin assumes an envelope conformation, with N3 atom at the flap position. The complex molecules are assembled by intermolecular N–H···O hydrogen bonding (Table 2). Lattice methanol molecule is linked with complex via O—H···O and N—H···O hydrogen bonding (Fig. 2).

Related literature top

For a related structure, see: Li et al. (2003).

Refinement top

Amino H atoms were located in a difference Fourier map and refined isotropically. Other H atoms were placed in calculated positions and allowed to ride on their attached atoms, with C—H = 0.93–0.97 Å, O–H = 0.82 Å, Uiso(H) = 1.2 or 1.5Ueq(C,O).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The atomic labeling scheme of (I) with displacement ellipsoids at the 30% probability level.
[Figure 2] Fig. 2. A packing diagram of the unit cell showing hydrogen bonds as dashed lines. H atoms, except for those involved in hydrogen bonds, are not included.
[Figure 3] Fig. 3. Interactive view of the complex.
(Aminoacetato-κ2O,N)bis(quinolin-8-olato- κ2O,N)cobalt(III) methanol solvate top
Crystal data top
[Co(C2H4NO2)(C9H6NO)2]·CH4OZ = 2
Mr = 453.33F000 = 468
Triclinic, P1Dx = 1.522 Mg m3
Hall symbol: -P 1Mo Kα radiation
λ = 0.71073 Å
a = 9.8377 (4) ÅCell parameters from 7882 reflections
b = 10.6526 (4) Åθ = 2.4–28.2º
c = 10.7369 (4) ŵ = 0.91 mm1
α = 82.047 (1)ºT = 273 (2) K
β = 76.289 (1)ºBlock, purple
γ = 64.941 (1)º0.20 × 0.15 × 0.12 mm
V = 989.32 (7) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
3261 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.017
Monochromator: graphiteθmax = 25.1º
φ and ω scansθmin = 2.0º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 9→11
Tmin = 0.840, Tmax = 0.899k = 12→12
11346 measured reflectionsl = 12→12
3486 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.028H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.094  w = 1/[σ2(Fo2) + (0.073P)2 + 0.17P]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.001
3486 reflectionsΔρmax = 0.28 e Å3
281 parametersΔρmin = 0.36 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Co(C2H4NO2)(C9H6NO)2]·CH4Oγ = 64.941 (1)º
Mr = 453.33V = 989.32 (7) Å3
Triclinic, P1Z = 2
a = 9.8377 (4) ÅMo Kα
b = 10.6526 (4) ŵ = 0.91 mm1
c = 10.7369 (4) ÅT = 273 (2) K
α = 82.047 (1)º0.20 × 0.15 × 0.12 mm
β = 76.289 (1)º
Data collection top
Bruker SMART CCD area-detector
diffractometer
3486 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
3261 reflections with I > 2σ(I)
Tmin = 0.840, Tmax = 0.899Rint = 0.017
11346 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.028281 parameters
wR(F2) = 0.094H atoms treated by a mixture of
independent and constrained refinement
S = 1.00Δρmax = 0.28 e Å3
3486 reflectionsΔρmin = 0.36 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Co10.21615 (2)0.26369 (2)0.46144 (2)0.03237 (12)
O10.36577 (14)0.20861 (13)0.56554 (12)0.0381 (3)
O20.46440 (17)0.29619 (16)0.67761 (14)0.0553 (4)
O30.05933 (15)0.33761 (13)0.60596 (13)0.0418 (3)
O40.06935 (14)0.32742 (13)0.35430 (13)0.0421 (3)
O50.4828 (3)0.4912 (3)0.2562 (2)0.1083 (9)
H50.49330.55730.27700.162*
N10.18775 (16)0.09298 (15)0.50938 (14)0.0348 (3)
N20.36569 (17)0.19377 (15)0.30857 (14)0.0349 (3)
N30.23374 (19)0.43960 (16)0.43835 (17)0.0397 (4)
C10.0225 (2)0.23999 (19)0.67578 (17)0.0391 (4)
C20.0769 (2)0.2598 (2)0.7924 (2)0.0539 (5)
H20.12310.34650.82790.065*
C30.1088 (3)0.1483 (3)0.8583 (2)0.0683 (7)
H30.17350.16260.93860.082*
C40.0487 (3)0.0206 (3)0.8091 (2)0.0656 (6)
H40.07440.04980.85430.079*
C50.0530 (2)0.0043 (2)0.6888 (2)0.0460 (5)
C60.1205 (2)0.1297 (2)0.6232 (2)0.0528 (5)
H60.09990.20570.66000.063*
C70.2144 (2)0.1391 (2)0.5076 (2)0.0504 (5)
H70.25670.22100.46420.060*
C80.2488 (2)0.02614 (18)0.45221 (19)0.0413 (4)
H80.31620.03540.37350.050*
C90.08930 (19)0.10617 (18)0.62504 (17)0.0364 (4)
C100.1360 (2)0.30635 (18)0.23300 (19)0.0422 (4)
C110.0622 (3)0.3473 (2)0.1301 (2)0.0590 (6)
H110.04350.39650.14390.071*
C120.1463 (4)0.3150 (3)0.0052 (2)0.0690 (7)
H120.09390.34450.06220.083*
C130.3015 (4)0.2421 (3)0.0224 (2)0.0657 (7)
H130.35300.22300.10680.079*
C140.3826 (3)0.1964 (2)0.07908 (19)0.0500 (5)
C150.5417 (3)0.1158 (2)0.0668 (2)0.0576 (5)
H150.60260.09030.01390.069*
C160.6059 (2)0.0755 (2)0.1726 (2)0.0558 (5)
H160.71010.02050.16450.067*
C170.5149 (2)0.1171 (2)0.29365 (19)0.0438 (4)
H170.56020.09040.36530.053*
C180.2987 (2)0.23139 (18)0.20409 (18)0.0393 (4)
C190.3819 (2)0.31043 (19)0.60261 (16)0.0392 (4)
C200.2899 (2)0.45316 (19)0.5487 (2)0.0452 (4)
H20A0.20400.50390.61440.054*
H20B0.35380.50470.52210.054*
C210.5849 (6)0.4394 (5)0.1517 (4)0.1377 (19)
H21A0.53430.43210.08850.207*
H21B0.65790.34900.17220.207*
H21C0.63670.49930.11830.207*
H220.143 (3)0.502 (3)0.436 (2)0.060 (7)*
H210.295 (3)0.444 (2)0.369 (2)0.048 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Co10.02705 (16)0.02604 (16)0.04380 (17)0.01193 (11)0.00651 (10)0.00211 (10)
O10.0359 (7)0.0324 (7)0.0464 (7)0.0132 (5)0.0107 (5)0.0006 (5)
O20.0585 (9)0.0602 (9)0.0529 (8)0.0229 (7)0.0185 (7)0.0116 (7)
O30.0365 (7)0.0317 (6)0.0529 (7)0.0144 (5)0.0006 (5)0.0027 (5)
O40.0315 (6)0.0366 (7)0.0594 (8)0.0142 (5)0.0147 (6)0.0056 (6)
O50.1061 (17)0.1167 (19)0.1255 (19)0.0846 (16)0.0328 (15)0.0453 (15)
N10.0294 (7)0.0310 (7)0.0468 (8)0.0139 (6)0.0126 (6)0.0036 (6)
N20.0330 (8)0.0318 (7)0.0431 (8)0.0165 (6)0.0089 (6)0.0020 (6)
N30.0316 (8)0.0305 (8)0.0567 (10)0.0144 (7)0.0078 (7)0.0035 (7)
C10.0321 (9)0.0415 (10)0.0468 (10)0.0187 (7)0.0087 (7)0.0023 (8)
C20.0489 (12)0.0610 (13)0.0523 (11)0.0273 (10)0.0013 (9)0.0072 (10)
C30.0685 (15)0.0868 (18)0.0532 (12)0.0460 (14)0.0061 (11)0.0020 (12)
C40.0710 (15)0.0741 (16)0.0641 (14)0.0506 (13)0.0070 (12)0.0173 (12)
C50.0414 (10)0.0463 (11)0.0589 (11)0.0272 (9)0.0163 (9)0.0131 (9)
C60.0506 (11)0.0379 (10)0.0813 (15)0.0285 (9)0.0242 (11)0.0152 (9)
C70.0458 (11)0.0330 (9)0.0788 (14)0.0189 (8)0.0193 (10)0.0011 (9)
C80.0377 (9)0.0336 (9)0.0547 (11)0.0146 (7)0.0135 (8)0.0003 (8)
C90.0310 (9)0.0374 (9)0.0461 (9)0.0185 (7)0.0135 (7)0.0070 (7)
C100.0461 (10)0.0310 (9)0.0590 (12)0.0226 (8)0.0218 (9)0.0108 (8)
C110.0656 (14)0.0484 (12)0.0783 (15)0.0302 (11)0.0415 (12)0.0196 (11)
C120.101 (2)0.0613 (15)0.0661 (15)0.0430 (15)0.0491 (15)0.0208 (12)
C130.104 (2)0.0626 (14)0.0471 (12)0.0481 (15)0.0239 (12)0.0099 (10)
C140.0691 (14)0.0482 (12)0.0451 (10)0.0369 (11)0.0115 (10)0.0026 (9)
C150.0618 (14)0.0653 (14)0.0516 (12)0.0374 (11)0.0071 (10)0.0148 (10)
C160.0408 (11)0.0627 (13)0.0630 (13)0.0224 (10)0.0013 (9)0.0159 (10)
C170.0340 (9)0.0455 (10)0.0523 (10)0.0160 (8)0.0078 (8)0.0051 (8)
C180.0472 (10)0.0330 (9)0.0463 (10)0.0241 (8)0.0143 (8)0.0062 (7)
C190.0337 (9)0.0423 (10)0.0383 (9)0.0145 (8)0.0010 (7)0.0084 (7)
C200.0412 (10)0.0362 (9)0.0614 (12)0.0182 (8)0.0087 (9)0.0070 (8)
C210.197 (5)0.142 (4)0.116 (3)0.129 (4)0.030 (3)0.047 (3)
Geometric parameters (Å, °) top
Co1—O11.9045 (12)C5—C61.417 (3)
Co1—O31.8926 (13)C6—C71.348 (3)
Co1—O41.9002 (13)C6—H60.9300
Co1—N11.9373 (14)C7—C81.403 (3)
Co1—N21.9179 (15)C7—H70.9300
Co1—N31.9309 (15)C8—H80.9300
O1—C191.287 (2)C10—C111.384 (3)
O2—C191.225 (2)C10—C181.431 (3)
O3—C11.323 (2)C11—C121.400 (4)
O4—C101.314 (2)C11—H110.9300
O5—C211.319 (4)C12—C131.367 (4)
O5—H50.8200C12—H120.9300
N1—C81.320 (2)C13—C141.413 (3)
N1—C91.365 (2)C13—H130.9300
N2—C171.326 (2)C14—C181.405 (3)
N2—C181.362 (2)C14—C151.413 (3)
N3—C201.468 (3)C15—C161.361 (3)
N3—H220.86 (3)C15—H150.9300
N3—H210.85 (2)C16—C171.399 (3)
C1—C21.374 (3)C16—H160.9300
C1—C91.419 (3)C17—H170.9300
C2—C31.410 (3)C19—C201.518 (3)
C2—H20.9300C20—H20A0.9700
C3—C41.359 (4)C20—H20B0.9700
C3—H30.9300C21—H21A0.9600
C4—C51.414 (3)C21—H21B0.9600
C4—H40.9300C21—H21C0.9600
C5—C91.414 (2)
O3—Co1—O490.60 (6)C6—C7—H7119.8
O3—Co1—O189.93 (6)C8—C7—H7119.8
O4—Co1—O1176.81 (5)N1—C8—C7121.45 (18)
O3—Co1—N2176.47 (5)N1—C8—H8119.3
O4—Co1—N285.88 (6)C7—C8—H8119.3
O1—Co1—N293.56 (6)N1—C9—C5122.64 (17)
O3—Co1—N387.07 (7)N1—C9—C1115.27 (15)
O4—Co1—N391.14 (6)C5—C9—C1122.07 (17)
O1—Co1—N385.75 (6)O4—C10—C11125.8 (2)
N2—Co1—N392.71 (7)O4—C10—C18117.56 (16)
O3—Co1—N185.82 (6)C11—C10—C18116.6 (2)
O4—Co1—N192.39 (6)C10—C11—C12120.2 (2)
O1—Co1—N190.79 (6)C10—C11—H11119.9
N2—Co1—N194.60 (6)C12—C11—H11119.9
N3—Co1—N1172.09 (7)C13—C12—C11123.2 (2)
C19—O1—Co1113.96 (11)C13—C12—H12118.4
C1—O3—Co1111.40 (11)C11—C12—H12118.4
C10—O4—Co1111.26 (11)C12—C13—C14119.0 (2)
C21—O5—H5109.5C12—C13—H13120.5
C8—N1—C9119.18 (15)C14—C13—H13120.5
C8—N1—Co1131.33 (13)C18—C14—C13117.7 (2)
C9—N1—Co1109.46 (12)C18—C14—C15116.45 (19)
C17—N2—C18119.37 (17)C13—C14—C15125.8 (2)
C17—N2—Co1129.99 (13)C16—C15—C14120.2 (2)
C18—N2—Co1110.63 (12)C16—C15—H15119.9
C20—N3—Co1107.24 (11)C14—C15—H15119.9
C20—N3—H22111.7 (16)C15—C16—C17119.9 (2)
Co1—N3—H22106.0 (17)C15—C16—H16120.1
C20—N3—H21110.4 (15)C17—C16—H16120.1
Co1—N3—H21111.4 (15)N2—C17—C16121.50 (18)
H22—N3—H21110 (2)N2—C17—H17119.3
O3—C1—C2124.64 (18)C16—C17—H17119.3
O3—C1—C9117.25 (15)N2—C18—C14122.54 (18)
C2—C1—C9118.10 (17)N2—C18—C10114.32 (17)
C1—C2—C3119.9 (2)C14—C18—C10123.13 (18)
C1—C2—H2120.1O2—C19—O1123.35 (17)
C3—C2—H2120.1O2—C19—C20120.82 (17)
C4—C3—C2122.5 (2)O1—C19—C20115.83 (15)
C4—C3—H3118.7N3—C20—C19109.90 (15)
C2—C3—H3118.7N3—C20—H20A109.7
C3—C4—C5119.62 (19)C19—C20—H20A109.7
C3—C4—H4120.2N3—C20—H20B109.7
C5—C4—H4120.2C19—C20—H20B109.7
C4—C5—C9117.7 (2)H20A—C20—H20B108.2
C4—C5—C6126.22 (19)O5—C21—H21A109.5
C9—C5—C6116.04 (18)O5—C21—H21B109.5
C7—C6—C5120.19 (17)H21A—C21—H21B109.5
C7—C6—H6119.9O5—C21—H21C109.5
C5—C6—H6119.9H21A—C21—H21C109.5
C6—C7—C8120.45 (19)H21B—C21—H21C109.5
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O5—H5···O2i0.821.922.743 (3)175
N3—H21···O50.85 (2)2.17 (3)2.950 (3)153 (2)
N3—H22···O3ii0.86 (3)2.10 (3)2.952 (2)169 (2)
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z+1.
Table 1
Selected geometric parameters (Å, °)
top
Co1—O11.9045 (12)Co1—N11.9373 (14)
Co1—O31.8926 (13)Co1—N21.9179 (15)
Co1—O41.9002 (13)Co1—N31.9309 (15)
O3—Co1—O490.60 (6)O1—Co1—N385.75 (6)
O3—Co1—O189.93 (6)N2—Co1—N392.71 (7)
O4—Co1—O1176.81 (5)O3—Co1—N185.82 (6)
O3—Co1—N2176.47 (5)O4—Co1—N192.39 (6)
O4—Co1—N285.88 (6)O1—Co1—N190.79 (6)
O1—Co1—N293.56 (6)N2—Co1—N194.60 (6)
O3—Co1—N387.07 (7)N3—Co1—N1172.09 (7)
O4—Co1—N391.14 (6)
Table 2
Hydrogen-bond geometry (Å, °)
top
D—H···AD—HH···AD···AD—H···A
O5—H5···O2i0.821.922.743 (3)175
N3—H21···O50.85 (2)2.17 (3)2.950 (3)153 (2)
N3—H22···O3ii0.86 (3)2.10 (3)2.952 (2)169 (2)
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z+1.
Acknowledgements top

This work was supported by the Youth Science Foundation of Shanxi Datong University, China (No. 2007Q08).

references
References top

Li, D.-X., Xu, D.-J., Gu, J.-M. & Xu, Y.-Z. (2003). Acta Cryst. E59, m543–m545.

Sheldrick, G. M. (1996). SADABS. University of GÖttingen, Germany.

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

Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.