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In the mol­ecule of the title compound, [Co(C9H6NO)3]·0.5C2H2O2·H2O, the Co atom has an octa­hedral coordination formed by three O and three N atoms from three quinolin-8-olate ligands. In the crystal structure, mol­ecules are linked into a three-dimensional framework by O—H...O hydrogen bonds. The supra­molecular structure is also consolidated by π–π stacking inter­actions. The glyoxal molecule lies on an inversion centre.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806050240/hk2166sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806050240/hk2166Isup2.hkl
Contains datablock I

CCDC reference: 1211235

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.045
  • wR factor = 0.144
  • Data-to-parameter ratio = 17.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for C10 - C18 .. 5.37 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Co1 - N1 .. 5.67 su
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXTL.

Tris(quinolin-8-olato-κ2N,O)cobalt(III) glyoxal hemisolvate monohydrate top
Crystal data top
[Co(C9H6NO)3]·0.5C2H2O2·H2OF(000) = 1108
Mr = 538.41Dx = 1.489 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 4873 reflections
a = 11.2532 (10) Åθ = 2.4–23.6°
b = 12.8237 (11) ŵ = 0.76 mm1
c = 16.7247 (14) ÅT = 273 K
β = 95.593 (1)°Prism, brown
V = 2402.0 (4) Å30.30 × 0.17 × 0.16 mm
Z = 4
Data collection top
Bruker APEX-II area-detector
diffractometer
5924 independent reflections
Radiation source: fine-focus sealed tube3137 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
φ and ω scansθmax = 28.3°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1515
Tmin = 0.804, Tmax = 0.888k = 1617
21478 measured reflectionsl = 2222
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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144H atoms treated by a mixture of independent and constrained refinement
S = 0.97 w = 1/[σ2(Fo2) + (0.1P)2 + 0.5743P]
where P = (Fo2 + 2Fc2)/3
5924 reflections(Δ/σ)max = 0.001
342 parametersΔρmax = 0.44 e Å3
6 restraintsΔρmin = 0.45 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
Co10.57352 (3)1.02143 (3)0.75742 (2)0.04898 (14)
O10.40732 (17)1.02488 (14)0.76898 (12)0.0545 (5)
O20.73908 (17)1.01380 (15)0.74154 (11)0.0566 (5)
O30.58694 (18)1.16328 (15)0.78873 (12)0.0593 (5)
O40.4108 (6)0.6382 (6)0.3070 (4)0.280 (4)
H4A0.4448 (16)0.5681 (10)0.3113 (11)0.280 (4)*
H4B0.436 (2)0.6425 (16)0.3595 (9)0.280 (6)*
O50.5293 (14)0.5690 (10)0.4149 (7)0.433 (7)
N10.5464 (2)0.87834 (18)0.72584 (13)0.0511 (5)
N20.5502 (2)1.06908 (19)0.64817 (13)0.0574 (6)
N30.61066 (19)0.98943 (17)0.87022 (13)0.0496 (5)
C10.3553 (2)0.9353 (2)0.74966 (15)0.0535 (7)
C20.2337 (3)0.9150 (3)0.74906 (19)0.0678 (8)
H20.18180.96770.76140.081*
C30.1896 (3)0.8148 (3)0.7299 (2)0.0778 (10)
H30.10840.80250.73140.093*
C40.2598 (3)0.7352 (3)0.70913 (19)0.0741 (9)
H40.22670.67010.69640.089*
C50.3841 (3)0.7520 (2)0.70707 (16)0.0592 (7)
C60.4683 (3)0.6782 (2)0.68503 (19)0.0696 (9)
H60.44350.61090.67100.083*
C70.5847 (3)0.7047 (2)0.6841 (2)0.0708 (9)
H70.63950.65540.66990.085*
C80.6227 (3)0.8059 (2)0.70465 (17)0.0602 (7)
H80.70280.82320.70350.072*
C90.4287 (2)0.8526 (2)0.72669 (15)0.0497 (6)
C100.7569 (3)1.0436 (2)0.66725 (18)0.0584 (7)
C110.8675 (3)1.0472 (2)0.6375 (2)0.0735 (9)
H110.93631.02870.66970.088*
C120.8740 (4)1.0798 (3)0.5569 (2)0.0861 (11)
H120.94831.08090.53700.103*
C130.7770 (4)1.1093 (3)0.5075 (2)0.0874 (11)
H130.78571.12990.45500.105*
C140.6633 (4)1.1085 (3)0.53581 (19)0.0740 (9)
C150.5562 (4)1.1399 (3)0.4933 (2)0.0885 (11)
H150.55651.16320.44060.106*
C160.4528 (4)1.1370 (3)0.5272 (2)0.0916 (11)
H160.38251.15930.49840.110*
C170.4512 (3)1.1004 (3)0.60588 (19)0.0747 (9)
H170.37921.09800.62880.090*
C180.6561 (3)1.0742 (2)0.61526 (16)0.0567 (7)
C190.6075 (2)1.1729 (2)0.86776 (17)0.0531 (7)
C200.6155 (3)1.2667 (2)0.90830 (19)0.0629 (8)
H200.60331.32900.88030.076*
C210.6421 (3)1.2675 (3)0.9922 (2)0.0701 (9)
H210.64801.33141.01860.084*
C220.6598 (3)1.1785 (3)1.0366 (2)0.0688 (8)
H220.67791.18231.09200.083*
C230.6504 (2)1.0809 (2)0.99785 (16)0.0558 (7)
C240.6630 (3)0.9833 (3)1.03614 (18)0.0653 (8)
H240.67980.97951.09160.078*
C250.6505 (3)0.8947 (3)0.99180 (18)0.0652 (8)
H250.65920.83031.01710.078*
C260.6246 (3)0.8993 (2)0.90842 (16)0.0572 (7)
H260.61700.83760.87920.069*
C270.6239 (2)1.0801 (2)0.91335 (16)0.0498 (6)
C280.4961 (17)0.5454 (10)0.4809 (9)0.336 (10)
H280.46060.59890.50760.403*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Co10.0512 (2)0.0511 (2)0.0456 (2)0.00072 (16)0.00968 (16)0.00169 (16)
O10.0549 (11)0.0539 (12)0.0563 (11)0.0034 (9)0.0139 (9)0.0056 (9)
O20.0523 (11)0.0658 (12)0.0530 (11)0.0048 (9)0.0109 (9)0.0041 (9)
O30.0744 (13)0.0490 (11)0.0552 (11)0.0020 (9)0.0097 (9)0.0067 (9)
O40.244 (7)0.367 (10)0.213 (6)0.154 (7)0.067 (5)0.112 (6)
O50.55 (2)0.425 (16)0.337 (15)0.126 (13)0.115 (14)0.041 (13)
N10.0537 (13)0.0585 (14)0.0425 (12)0.0049 (11)0.0116 (10)0.0002 (10)
N20.0647 (15)0.0589 (15)0.0494 (13)0.0024 (12)0.0089 (11)0.0041 (11)
N30.0516 (13)0.0512 (13)0.0472 (12)0.0005 (10)0.0112 (10)0.0011 (10)
C10.0557 (17)0.0614 (17)0.0446 (15)0.0015 (14)0.0113 (12)0.0010 (13)
C20.0490 (17)0.083 (2)0.073 (2)0.0034 (16)0.0116 (14)0.0068 (17)
C30.0591 (19)0.105 (3)0.071 (2)0.020 (2)0.0106 (16)0.005 (2)
C40.081 (2)0.075 (2)0.067 (2)0.0242 (19)0.0121 (17)0.0025 (17)
C50.0711 (19)0.0593 (18)0.0483 (15)0.0093 (15)0.0115 (14)0.0039 (13)
C60.095 (3)0.0508 (17)0.064 (2)0.0022 (17)0.0135 (17)0.0007 (14)
C70.087 (2)0.0553 (19)0.072 (2)0.0133 (17)0.0157 (18)0.0063 (16)
C80.0616 (17)0.0666 (19)0.0539 (17)0.0094 (15)0.0128 (14)0.0003 (14)
C90.0512 (15)0.0571 (17)0.0419 (14)0.0029 (12)0.0106 (12)0.0010 (11)
C100.0685 (18)0.0485 (16)0.0619 (18)0.0109 (13)0.0255 (15)0.0077 (13)
C110.069 (2)0.0615 (19)0.094 (3)0.0125 (15)0.0305 (18)0.0129 (17)
C120.095 (3)0.081 (2)0.092 (3)0.023 (2)0.057 (2)0.014 (2)
C130.125 (3)0.072 (2)0.071 (2)0.018 (2)0.040 (2)0.0011 (19)
C140.108 (3)0.0618 (19)0.0561 (18)0.0058 (18)0.0294 (19)0.0011 (15)
C150.124 (3)0.088 (3)0.055 (2)0.006 (2)0.012 (2)0.0159 (19)
C160.100 (3)0.111 (3)0.063 (2)0.024 (2)0.003 (2)0.021 (2)
C170.073 (2)0.088 (2)0.0620 (19)0.0122 (18)0.0044 (16)0.0061 (17)
C180.073 (2)0.0498 (16)0.0495 (15)0.0037 (14)0.0165 (14)0.0020 (13)
C190.0514 (15)0.0530 (16)0.0571 (17)0.0022 (12)0.0160 (13)0.0002 (13)
C200.0618 (18)0.0509 (17)0.078 (2)0.0017 (14)0.0148 (15)0.0005 (15)
C210.069 (2)0.066 (2)0.077 (2)0.0034 (16)0.0132 (16)0.0241 (18)
C220.070 (2)0.081 (2)0.0559 (18)0.0018 (17)0.0105 (15)0.0131 (16)
C230.0550 (16)0.0644 (19)0.0497 (16)0.0013 (14)0.0136 (12)0.0054 (14)
C240.073 (2)0.078 (2)0.0453 (15)0.0060 (16)0.0085 (14)0.0059 (15)
C250.080 (2)0.0643 (19)0.0528 (17)0.0038 (16)0.0125 (15)0.0136 (15)
C260.0686 (18)0.0499 (16)0.0548 (17)0.0008 (14)0.0141 (14)0.0040 (13)
C270.0463 (14)0.0543 (16)0.0507 (15)0.0010 (12)0.0134 (12)0.0001 (13)
C280.50 (2)0.233 (14)0.321 (19)0.003 (18)0.263 (19)0.038 (13)
Geometric parameters (Å, º) top
Co1—O11.8994 (19)C10—C111.386 (4)
Co1—O21.9099 (19)C10—C181.415 (4)
Co1—O31.895 (2)C11—C121.420 (5)
Co1—N11.926 (2)C11—H110.9300
Co1—N21.920 (2)C12—C131.357 (6)
Co1—N31.936 (2)C12—H120.9300
O1—C11.315 (3)C13—C141.408 (5)
O2—C101.333 (3)C13—H130.9300
O3—C191.325 (3)C14—C151.397 (5)
O4—H4A0.977 (11)C14—C181.409 (4)
O4—H4B0.897 (12)C15—C161.344 (5)
O5—C281.238 (12)C15—H150.9300
N1—C81.336 (3)C16—C171.399 (5)
N1—C91.366 (3)C16—H160.9300
N2—C171.322 (4)C17—H170.9300
N2—C181.363 (3)C19—C201.380 (4)
N3—C261.322 (3)C19—C271.415 (4)
N3—C271.369 (3)C20—C211.406 (4)
C1—C21.392 (4)C20—H200.9300
C1—C91.420 (4)C21—C221.365 (5)
C2—C31.403 (5)C21—H210.9300
C2—H20.9300C22—C231.409 (4)
C3—C41.357 (5)C22—H220.9300
C3—H30.9300C23—C241.407 (4)
C4—C51.420 (4)C23—C271.416 (4)
C4—H40.9300C24—C251.356 (4)
C5—C91.412 (4)C24—H240.9300
C5—C61.413 (4)C25—C261.398 (4)
C6—C71.356 (4)C25—H250.9300
C6—H60.9300C26—H260.9300
C7—C81.399 (4)C28—C28i1.33 (2)
C7—H70.9300C28—H280.9300
C8—H80.9300
O1—Co1—O2177.32 (8)O2—C10—C18117.9 (3)
O1—Co1—O390.13 (8)C11—C10—C18117.6 (3)
O2—Co1—O392.01 (8)C10—C11—C12118.8 (3)
O1—Co1—N185.33 (9)C10—C11—H11120.6
O1—Co1—N292.56 (9)C12—C11—H11120.6
O1—Co1—N391.54 (9)C13—C12—C11123.2 (3)
O2—Co1—N192.51 (9)C13—C12—H12118.4
O2—Co1—N285.92 (9)C11—C12—H12118.4
O2—Co1—N390.22 (9)C12—C13—C14119.8 (3)
O3—Co1—N1175.44 (9)C12—C13—H13120.1
O3—Co1—N287.56 (9)C14—C13—H13120.1
O3—Co1—N386.01 (9)C15—C14—C13126.4 (3)
N1—Co1—N292.23 (10)C15—C14—C18116.4 (3)
N1—Co1—N394.51 (9)C13—C14—C18117.2 (3)
N2—Co1—N3172.38 (10)C16—C15—C14121.1 (3)
C1—O1—Co1111.97 (16)C16—C15—H15119.5
C10—O2—Co1110.60 (18)C14—C15—H15119.5
C19—O3—Co1111.47 (16)C15—C16—C17119.8 (4)
H4A—O4—H4B84.3 (13)C15—C16—H16120.1
C8—N1—C9118.9 (3)C17—C16—H16120.1
C8—N1—Co1130.3 (2)N2—C17—C16121.2 (3)
C9—N1—Co1110.81 (18)N2—C17—H17119.4
C17—N2—C18119.6 (3)C16—C17—H17119.4
C17—N2—Co1129.5 (2)N2—C18—C14121.9 (3)
C18—N2—Co1110.83 (18)N2—C18—C10114.7 (2)
C26—N3—C27119.1 (2)C14—C18—C10123.4 (3)
C26—N3—Co1131.3 (2)O3—C19—C20124.6 (3)
C27—N3—Co1109.60 (17)O3—C19—C27117.4 (2)
O1—C1—C2125.4 (3)C20—C19—C27118.0 (3)
O1—C1—C9117.5 (2)C19—C20—C21119.6 (3)
C2—C1—C9117.1 (3)C19—C20—H20120.2
C1—C2—C3120.0 (3)C21—C20—H20120.2
C1—C2—H2120.0C22—C21—C20122.9 (3)
C3—C2—H2120.0C22—C21—H21118.6
C4—C3—C2123.1 (3)C20—C21—H21118.6
C4—C3—H3118.5C21—C22—C23119.4 (3)
C2—C3—H3118.5C21—C22—H22120.3
C3—C4—C5119.5 (3)C23—C22—H22120.3
C3—C4—H4120.3C24—C23—C22125.5 (3)
C5—C4—H4120.3C24—C23—C27116.7 (3)
C9—C5—C6116.1 (3)C22—C23—C27117.7 (3)
C9—C5—C4117.5 (3)C25—C24—C23119.7 (3)
C6—C5—C4126.3 (3)C25—C24—H24120.1
C7—C6—C5120.6 (3)C23—C24—H24120.1
C7—C6—H6119.7C24—C25—C26120.7 (3)
C5—C6—H6119.7C24—C25—H25119.6
C6—C7—C8120.1 (3)C26—C25—H25119.6
C6—C7—H7119.9N3—C26—C25121.5 (3)
C8—C7—H7119.9N3—C26—H26119.3
N1—C8—C7121.4 (3)C25—C26—H26119.3
N1—C8—H8119.3N3—C27—C19115.4 (2)
C7—C8—H8119.3N3—C27—C23122.2 (2)
N1—C9—C5122.8 (3)C19—C27—C23122.4 (3)
N1—C9—C1114.4 (2)O5—C28—C28i129 (2)
C5—C9—C1122.8 (2)O5—C28—H28115.4
O2—C10—C11124.4 (3)C28i—C28—H28115.4
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4B···O50.90 (1)1.63 (2)2.314 (16)130 (2)
 

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