Retracted: Tris(quinolin-8-olato-κ²N,O)cobalt(III) glyoxal hemisolvate monohydrate

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.

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

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Computing details

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

Crystal data

[Co(C9H6NO)3]·0.5C2H2O2·H2O	F(000) = 1108
Mr = 538.41	Dx = 1.489 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4873 reflections
a = 11.2532 (10) Å	θ = 2.4–23.6°
b = 12.8237 (11) Å	µ = 0.76 mm^−1
c = 16.7247 (14) Å	T = 273 K
β = 95.593 (1)°	Prism, brown
V = 2402.0 (4) Å^3	0.30 × 0.17 × 0.16 mm
Z = 4

Data collection

Bruker APEX-II area-detector diffractometer	5924 independent reflections
Radiation source: fine-focus sealed tube	3137 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
φ and ω scans	θmax = 28.3°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
Tmin = 0.804, Tmax = 0.888	k = −16→17
21478 measured reflections	l = −22→22

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.144	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	w = 1/[σ^2(Fo^2) + (0.1P)^2 + 0.5743P] where P = (Fo^2 + 2Fc^2)/3
5924 reflections	(Δ/σ)max = 0.001
342 parameters	Δρmax = 0.44 e Å^−3
6 restraints	Δρmin = −0.45 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Co1	0.57352 (3)	1.02143 (3)	0.75742 (2)	0.04898 (14)
O1	0.40732 (17)	1.02488 (14)	0.76898 (12)	0.0545 (5)
O2	0.73908 (17)	1.01380 (15)	0.74154 (11)	0.0566 (5)
O3	0.58694 (18)	1.16328 (15)	0.78873 (12)	0.0593 (5)
O4	0.4108 (6)	0.6382 (6)	0.3070 (4)	0.280 (4)
H4A	0.4448 (16)	0.5681 (10)	0.3113 (11)	0.280 (4)*
H4B	0.436 (2)	0.6425 (16)	0.3595 (9)	0.280 (6)*
O5	0.5293 (14)	0.5690 (10)	0.4149 (7)	0.433 (7)
N1	0.5464 (2)	0.87834 (18)	0.72584 (13)	0.0511 (5)
N2	0.5502 (2)	1.06908 (19)	0.64817 (13)	0.0574 (6)
N3	0.61066 (19)	0.98943 (17)	0.87022 (13)	0.0496 (5)
C1	0.3553 (2)	0.9353 (2)	0.74966 (15)	0.0535 (7)
C2	0.2337 (3)	0.9150 (3)	0.74906 (19)	0.0678 (8)
H2	0.1818	0.9677	0.7614	0.081*
C3	0.1896 (3)	0.8148 (3)	0.7299 (2)	0.0778 (10)
H3	0.1084	0.8025	0.7314	0.093*
C4	0.2598 (3)	0.7352 (3)	0.70913 (19)	0.0741 (9)
H4	0.2267	0.6701	0.6964	0.089*
C5	0.3841 (3)	0.7520 (2)	0.70707 (16)	0.0592 (7)
C6	0.4683 (3)	0.6782 (2)	0.68503 (19)	0.0696 (9)
H6	0.4435	0.6109	0.6710	0.083*
C7	0.5847 (3)	0.7047 (2)	0.6841 (2)	0.0708 (9)
H7	0.6395	0.6554	0.6699	0.085*
C8	0.6227 (3)	0.8059 (2)	0.70465 (17)	0.0602 (7)
H8	0.7028	0.8232	0.7035	0.072*
C9	0.4287 (2)	0.8526 (2)	0.72669 (15)	0.0497 (6)
C10	0.7569 (3)	1.0436 (2)	0.66725 (18)	0.0584 (7)
C11	0.8675 (3)	1.0472 (2)	0.6375 (2)	0.0735 (9)
H11	0.9363	1.0287	0.6697	0.088*
C12	0.8740 (4)	1.0798 (3)	0.5569 (2)	0.0861 (11)
H12	0.9483	1.0809	0.5370	0.103*
C13	0.7770 (4)	1.1093 (3)	0.5075 (2)	0.0874 (11)
H13	0.7857	1.1299	0.4550	0.105*
C14	0.6633 (4)	1.1085 (3)	0.53581 (19)	0.0740 (9)
C15	0.5562 (4)	1.1399 (3)	0.4933 (2)	0.0885 (11)
H15	0.5565	1.1632	0.4406	0.106*
C16	0.4528 (4)	1.1370 (3)	0.5272 (2)	0.0916 (11)
H16	0.3825	1.1593	0.4984	0.110*
C17	0.4512 (3)	1.1004 (3)	0.60588 (19)	0.0747 (9)
H17	0.3792	1.0980	0.6288	0.090*
C18	0.6561 (3)	1.0742 (2)	0.61526 (16)	0.0567 (7)
C19	0.6075 (2)	1.1729 (2)	0.86776 (17)	0.0531 (7)
C20	0.6155 (3)	1.2667 (2)	0.90830 (19)	0.0629 (8)
H20	0.6033	1.3290	0.8803	0.076*
C21	0.6421 (3)	1.2675 (3)	0.9922 (2)	0.0701 (9)
H21	0.6480	1.3314	1.0186	0.084*
C22	0.6598 (3)	1.1785 (3)	1.0366 (2)	0.0688 (8)
H22	0.6779	1.1823	1.0920	0.083*
C23	0.6504 (2)	1.0809 (2)	0.99785 (16)	0.0558 (7)
C24	0.6630 (3)	0.9833 (3)	1.03614 (18)	0.0653 (8)
H24	0.6798	0.9795	1.0916	0.078*
C25	0.6505 (3)	0.8947 (3)	0.99180 (18)	0.0652 (8)
H25	0.6592	0.8303	1.0171	0.078*
C26	0.6246 (3)	0.8993 (2)	0.90842 (16)	0.0572 (7)
H26	0.6170	0.8376	0.8792	0.069*
C27	0.6239 (2)	1.0801 (2)	0.91335 (16)	0.0498 (6)
C28	0.4961 (17)	0.5454 (10)	0.4809 (9)	0.336 (10)
H28	0.4606	0.5989	0.5076	0.403*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.0512 (2)	0.0511 (2)	0.0456 (2)	−0.00072 (16)	0.00968 (16)	0.00169 (16)
O1	0.0549 (11)	0.0539 (12)	0.0563 (11)	0.0034 (9)	0.0139 (9)	−0.0056 (9)
O2	0.0523 (11)	0.0658 (12)	0.0530 (11)	−0.0048 (9)	0.0109 (9)	0.0041 (9)
O3	0.0744 (13)	0.0490 (11)	0.0552 (11)	−0.0020 (9)	0.0097 (9)	0.0067 (9)
O4	0.244 (7)	0.367 (10)	0.213 (6)	−0.154 (7)	−0.067 (5)	0.112 (6)
O5	0.55 (2)	0.425 (16)	0.337 (15)	−0.126 (13)	0.115 (14)	0.041 (13)
N1	0.0537 (13)	0.0585 (14)	0.0425 (12)	0.0049 (11)	0.0116 (10)	0.0002 (10)
N2	0.0647 (15)	0.0589 (15)	0.0494 (13)	0.0024 (12)	0.0089 (11)	0.0041 (11)
N3	0.0516 (13)	0.0512 (13)	0.0472 (12)	−0.0005 (10)	0.0112 (10)	0.0011 (10)
C1	0.0557 (17)	0.0614 (17)	0.0446 (15)	−0.0015 (14)	0.0113 (12)	−0.0010 (13)
C2	0.0490 (17)	0.083 (2)	0.073 (2)	0.0034 (16)	0.0116 (14)	−0.0068 (17)
C3	0.0591 (19)	0.105 (3)	0.071 (2)	−0.020 (2)	0.0106 (16)	−0.005 (2)
C4	0.081 (2)	0.075 (2)	0.067 (2)	−0.0242 (19)	0.0121 (17)	−0.0025 (17)
C5	0.0711 (19)	0.0593 (18)	0.0483 (15)	−0.0093 (15)	0.0115 (14)	0.0039 (13)
C6	0.095 (3)	0.0508 (17)	0.064 (2)	−0.0022 (17)	0.0135 (17)	−0.0007 (14)
C7	0.087 (2)	0.0553 (19)	0.072 (2)	0.0133 (17)	0.0157 (18)	−0.0063 (16)
C8	0.0616 (17)	0.0666 (19)	0.0539 (17)	0.0094 (15)	0.0128 (14)	−0.0003 (14)
C9	0.0512 (15)	0.0571 (17)	0.0419 (14)	−0.0029 (12)	0.0106 (12)	0.0010 (11)
C10	0.0685 (18)	0.0485 (16)	0.0619 (18)	−0.0109 (13)	0.0255 (15)	−0.0077 (13)
C11	0.069 (2)	0.0615 (19)	0.094 (3)	−0.0125 (15)	0.0305 (18)	−0.0129 (17)
C12	0.095 (3)	0.081 (2)	0.092 (3)	−0.023 (2)	0.057 (2)	−0.014 (2)
C13	0.125 (3)	0.072 (2)	0.071 (2)	−0.018 (2)	0.040 (2)	−0.0011 (19)
C14	0.108 (3)	0.0618 (19)	0.0561 (18)	−0.0058 (18)	0.0294 (19)	−0.0011 (15)
C15	0.124 (3)	0.088 (3)	0.055 (2)	0.006 (2)	0.012 (2)	0.0159 (19)
C16	0.100 (3)	0.111 (3)	0.063 (2)	0.024 (2)	0.003 (2)	0.021 (2)
C17	0.073 (2)	0.088 (2)	0.0620 (19)	0.0122 (18)	0.0044 (16)	0.0061 (17)
C18	0.073 (2)	0.0498 (16)	0.0495 (15)	−0.0037 (14)	0.0165 (14)	−0.0020 (13)
C19	0.0514 (15)	0.0530 (16)	0.0571 (17)	−0.0022 (12)	0.0160 (13)	−0.0002 (13)
C20	0.0618 (18)	0.0509 (17)	0.078 (2)	−0.0017 (14)	0.0148 (15)	−0.0005 (15)
C21	0.069 (2)	0.066 (2)	0.077 (2)	−0.0034 (16)	0.0132 (16)	−0.0241 (18)
C22	0.070 (2)	0.081 (2)	0.0559 (18)	−0.0018 (17)	0.0105 (15)	−0.0131 (16)
C23	0.0550 (16)	0.0644 (19)	0.0497 (16)	−0.0013 (14)	0.0136 (12)	−0.0054 (14)
C24	0.073 (2)	0.078 (2)	0.0453 (15)	0.0060 (16)	0.0085 (14)	0.0059 (15)
C25	0.080 (2)	0.0643 (19)	0.0528 (17)	0.0038 (16)	0.0125 (15)	0.0136 (15)
C26	0.0686 (18)	0.0499 (16)	0.0548 (17)	−0.0008 (14)	0.0141 (14)	0.0040 (13)
C27	0.0463 (14)	0.0543 (16)	0.0507 (15)	−0.0010 (12)	0.0134 (12)	−0.0001 (13)
C28	0.50 (2)	0.233 (14)	0.321 (19)	−0.003 (18)	0.263 (19)	0.038 (13)

Geometric parameters (Å, º)

Co1—O1	1.8994 (19)	C10—C11	1.386 (4)
Co1—O2	1.9099 (19)	C10—C18	1.415 (4)
Co1—O3	1.895 (2)	C11—C12	1.420 (5)
Co1—N1	1.926 (2)	C11—H11	0.9300
Co1—N2	1.920 (2)	C12—C13	1.357 (6)
Co1—N3	1.936 (2)	C12—H12	0.9300
O1—C1	1.315 (3)	C13—C14	1.408 (5)
O2—C10	1.333 (3)	C13—H13	0.9300
O3—C19	1.325 (3)	C14—C15	1.397 (5)
O4—H4A	0.977 (11)	C14—C18	1.409 (4)
O4—H4B	0.897 (12)	C15—C16	1.344 (5)
O5—C28	1.238 (12)	C15—H15	0.9300
N1—C8	1.336 (3)	C16—C17	1.399 (5)
N1—C9	1.366 (3)	C16—H16	0.9300
N2—C17	1.322 (4)	C17—H17	0.9300
N2—C18	1.363 (3)	C19—C20	1.380 (4)
N3—C26	1.322 (3)	C19—C27	1.415 (4)
N3—C27	1.369 (3)	C20—C21	1.406 (4)
C1—C2	1.392 (4)	C20—H20	0.9300
C1—C9	1.420 (4)	C21—C22	1.365 (5)
C2—C3	1.403 (5)	C21—H21	0.9300
C2—H2	0.9300	C22—C23	1.409 (4)
C3—C4	1.357 (5)	C22—H22	0.9300
C3—H3	0.9300	C23—C24	1.407 (4)
C4—C5	1.420 (4)	C23—C27	1.416 (4)
C4—H4	0.9300	C24—C25	1.356 (4)
C5—C9	1.412 (4)	C24—H24	0.9300
C5—C6	1.413 (4)	C25—C26	1.398 (4)
C6—C7	1.356 (4)	C25—H25	0.9300
C6—H6	0.9300	C26—H26	0.9300
C7—C8	1.399 (4)	C28—C28^i	1.33 (2)
C7—H7	0.9300	C28—H28	0.9300
C8—H8	0.9300
O1—Co1—O2	177.32 (8)	O2—C10—C18	117.9 (3)
O1—Co1—O3	90.13 (8)	C11—C10—C18	117.6 (3)
O2—Co1—O3	92.01 (8)	C10—C11—C12	118.8 (3)
O1—Co1—N1	85.33 (9)	C10—C11—H11	120.6
O1—Co1—N2	92.56 (9)	C12—C11—H11	120.6
O1—Co1—N3	91.54 (9)	C13—C12—C11	123.2 (3)
O2—Co1—N1	92.51 (9)	C13—C12—H12	118.4
O2—Co1—N2	85.92 (9)	C11—C12—H12	118.4
O2—Co1—N3	90.22 (9)	C12—C13—C14	119.8 (3)
O3—Co1—N1	175.44 (9)	C12—C13—H13	120.1
O3—Co1—N2	87.56 (9)	C14—C13—H13	120.1
O3—Co1—N3	86.01 (9)	C15—C14—C13	126.4 (3)
N1—Co1—N2	92.23 (10)	C15—C14—C18	116.4 (3)
N1—Co1—N3	94.51 (9)	C13—C14—C18	117.2 (3)
N2—Co1—N3	172.38 (10)	C16—C15—C14	121.1 (3)
C1—O1—Co1	111.97 (16)	C16—C15—H15	119.5
C10—O2—Co1	110.60 (18)	C14—C15—H15	119.5
C19—O3—Co1	111.47 (16)	C15—C16—C17	119.8 (4)
H4A—O4—H4B	84.3 (13)	C15—C16—H16	120.1
C8—N1—C9	118.9 (3)	C17—C16—H16	120.1
C8—N1—Co1	130.3 (2)	N2—C17—C16	121.2 (3)
C9—N1—Co1	110.81 (18)	N2—C17—H17	119.4
C17—N2—C18	119.6 (3)	C16—C17—H17	119.4
C17—N2—Co1	129.5 (2)	N2—C18—C14	121.9 (3)
C18—N2—Co1	110.83 (18)	N2—C18—C10	114.7 (2)
C26—N3—C27	119.1 (2)	C14—C18—C10	123.4 (3)
C26—N3—Co1	131.3 (2)	O3—C19—C20	124.6 (3)
C27—N3—Co1	109.60 (17)	O3—C19—C27	117.4 (2)
O1—C1—C2	125.4 (3)	C20—C19—C27	118.0 (3)
O1—C1—C9	117.5 (2)	C19—C20—C21	119.6 (3)
C2—C1—C9	117.1 (3)	C19—C20—H20	120.2
C1—C2—C3	120.0 (3)	C21—C20—H20	120.2
C1—C2—H2	120.0	C22—C21—C20	122.9 (3)
C3—C2—H2	120.0	C22—C21—H21	118.6
C4—C3—C2	123.1 (3)	C20—C21—H21	118.6
C4—C3—H3	118.5	C21—C22—C23	119.4 (3)
C2—C3—H3	118.5	C21—C22—H22	120.3
C3—C4—C5	119.5 (3)	C23—C22—H22	120.3
C3—C4—H4	120.3	C24—C23—C22	125.5 (3)
C5—C4—H4	120.3	C24—C23—C27	116.7 (3)
C9—C5—C6	116.1 (3)	C22—C23—C27	117.7 (3)
C9—C5—C4	117.5 (3)	C25—C24—C23	119.7 (3)
C6—C5—C4	126.3 (3)	C25—C24—H24	120.1
C7—C6—C5	120.6 (3)	C23—C24—H24	120.1
C7—C6—H6	119.7	C24—C25—C26	120.7 (3)
C5—C6—H6	119.7	C24—C25—H25	119.6
C6—C7—C8	120.1 (3)	C26—C25—H25	119.6
C6—C7—H7	119.9	N3—C26—C25	121.5 (3)
C8—C7—H7	119.9	N3—C26—H26	119.3
N1—C8—C7	121.4 (3)	C25—C26—H26	119.3
N1—C8—H8	119.3	N3—C27—C19	115.4 (2)
C7—C8—H8	119.3	N3—C27—C23	122.2 (2)
N1—C9—C5	122.8 (3)	C19—C27—C23	122.4 (3)
N1—C9—C1	114.4 (2)	O5—C28—C28^i	129 (2)
C5—C9—C1	122.8 (2)	O5—C28—H28	115.4
O2—C10—C11	124.4 (3)	C28^i—C28—H28	115.4

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4B···O5	0.90 (1)	1.63 (2)	2.314 (16)	130 (2)