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The NiII atom in the title complex, [Ni(C9H6NO)2(C9H7NO)]·0.5C2H2O2·H2O, has an octa­hedral coordination geometry defined by three O and three N atoms from one 8-hydoxyquinoline and two 8-oxoquinaoline ligands. The glyoxal molecule lies on an inversion centre. In the crystal structure, mol­ecules are linked into a three-dimensional framework by O—H...O hydrogen bonds and π–π stacking inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806053232/ci2229sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806053232/ci2229Isup2.hkl
Contains datablock I

CCDC reference: 1211535

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.052
  • wR factor = 0.162
  • Data-to-parameter ratio = 16.9

checkCIF/PLATON results

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Alert level B PLAT417_ALERT_2_B Short Inter D-H..H-D H2A .. H4A .. 1.80 Ang.
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 0 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 1 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.

(8-Quinolinol-κ2N,O)bis(8-quinolinolato-κ2N,O)nickel(II) glyoxal hemisolvate monohydrate top
Crystal data top
[Ni(C9H6NO)2(C9H7NO)]·0.5C2H2O2·H2OF(000) = 1116
Mr = 539.20Dx = 1.491 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 4883 reflections
a = 11.2532 (10) Åθ = 2.4–23.6°
b = 12.8237 (11) ŵ = 0.85 mm1
c = 16.7247 (14) ÅT = 273 K
β = 95.593 (1)°Prism, green
V = 2402.0 (4) Å30.30 × 0.17 × 0.16 mm
Z = 4
Data collection top
Bruker APEX-II area-detector
diffractometer
5764 independent reflections
Radiation source: fine-focus sealed tube3135 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
φ and ω scansθmax = 27.9°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1414
Tmin = 0.832, Tmax = 0.876k = 1616
21232 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)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.162H atoms treated by a mixture of independent and constrained refinement
S = 0.99 w = 1/[σ2(Fo2) + (0.1P)2 + 0.5743P]
where P = (Fo2 + 2Fc2)/3
5764 reflections(Δ/σ)max = 0.001
342 parametersΔρmax = 0.49 e Å3
3 restraintsΔρmin = 0.48 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
Ni10.57355 (4)1.02141 (3)0.75746 (2)0.05061 (17)
O10.40720 (19)1.02488 (16)0.76903 (13)0.0515 (5)
O20.73853 (19)1.01424 (17)0.74095 (13)0.0535 (5)
H2A0.79840.99280.77970.064*
O30.5870 (2)1.16325 (16)0.78887 (13)0.0565 (6)
O40.4118 (7)0.6359 (7)0.3081 (5)0.108 (5)
O50.5276 (15)0.5702 (11)0.4177 (8)0.116 (8)
N10.5462 (2)0.8785 (2)0.72585 (14)0.0487 (6)
N20.5499 (2)1.0691 (2)0.64806 (15)0.0545 (7)
N30.6107 (2)0.98950 (19)0.87020 (15)0.0466 (6)
C10.3553 (3)0.9358 (3)0.74962 (17)0.0509 (8)
C20.2337 (3)0.9148 (3)0.7488 (2)0.0652 (9)
H20.18160.96760.76090.078*
C30.1893 (3)0.8150 (4)0.7298 (2)0.0751 (11)
H30.10810.80280.73140.090*
C40.2594 (4)0.7354 (3)0.7092 (2)0.0715 (10)
H40.22640.67030.69660.086*
C50.3841 (3)0.7522 (3)0.70711 (19)0.0569 (8)
C60.4685 (4)0.6781 (3)0.6850 (2)0.0666 (10)
H60.44370.61090.67090.080*
C70.5846 (4)0.7042 (3)0.6840 (2)0.0676 (10)
H70.63930.65490.66980.081*
C80.6228 (3)0.8062 (3)0.70460 (19)0.0580 (8)
H80.70290.82350.70340.070*
C90.4289 (3)0.8527 (3)0.72675 (17)0.0468 (7)
C100.7571 (3)1.0437 (2)0.6673 (2)0.0550 (8)
C110.8675 (4)1.0473 (3)0.6377 (3)0.0707 (10)
H110.93631.02880.66990.085*
C120.8738 (4)1.0801 (3)0.5569 (3)0.0831 (13)
H120.94821.08140.53700.100*
C130.7770 (5)1.1096 (3)0.5076 (3)0.0839 (13)
H130.78561.13040.45520.101*
C140.6636 (4)1.1086 (3)0.5360 (2)0.0711 (10)
C150.5553 (5)1.1394 (3)0.4929 (2)0.0846 (12)
H150.55511.16200.44000.102*
C160.4533 (4)1.1366 (4)0.5271 (2)0.0871 (13)
H160.38291.15890.49850.104*
C170.4514 (3)1.1003 (3)0.6058 (2)0.0711 (10)
H170.37931.09810.62860.085*
C180.6564 (3)1.0742 (2)0.61523 (19)0.0544 (8)
C190.6073 (3)1.1728 (2)0.86768 (19)0.0506 (7)
C200.6155 (3)1.2669 (3)0.9082 (2)0.0604 (9)
H200.60361.32930.88030.072*
C210.6422 (3)1.2673 (3)0.9923 (2)0.0674 (10)
H210.64811.33121.01880.081*
C220.6596 (3)1.1785 (3)1.0365 (2)0.0656 (9)
H220.67751.18211.09190.079*
C230.6505 (3)1.0811 (3)0.99771 (19)0.0531 (8)
C240.6630 (3)0.9831 (3)1.0360 (2)0.0629 (9)
H240.67980.97931.09150.075*
C250.6505 (3)0.8945 (3)0.9917 (2)0.0617 (9)
H250.65930.83001.01700.074*
C260.6244 (3)0.8993 (3)0.90843 (19)0.0544 (8)
H260.61660.83760.87910.065*
C270.6240 (3)1.0800 (2)0.91327 (18)0.0476 (7)
C280.495 (2)0.5454 (12)0.4831 (10)0.105 (12)
H280.45970.59740.51140.376*
H4A0.440 (2)0.5699 (12)0.3069 (14)0.271 (6)*
H4B0.434 (3)0.650 (2)0.3579 (10)0.272 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0529 (3)0.0528 (3)0.0472 (3)0.00078 (19)0.00994 (18)0.00169 (18)
O10.0520 (12)0.0515 (13)0.0528 (12)0.0041 (10)0.0146 (10)0.0052 (10)
O20.0469 (12)0.0649 (14)0.0489 (12)0.0029 (10)0.0062 (10)0.0058 (10)
O30.0723 (15)0.0454 (12)0.0523 (13)0.0020 (10)0.0093 (11)0.0064 (10)
O40.247 (8)0.364 (11)0.214 (7)0.180 (8)0.057 (6)0.084 (8)
O50.54 (2)0.403 (18)0.315 (15)0.132 (14)0.099 (16)0.014 (14)
N10.0521 (15)0.0549 (15)0.0404 (13)0.0056 (12)0.0113 (11)0.0006 (12)
N20.0621 (17)0.0559 (17)0.0459 (15)0.0023 (13)0.0081 (13)0.0043 (12)
N30.0484 (14)0.0481 (14)0.0446 (13)0.0002 (11)0.0107 (11)0.0013 (11)
C10.0526 (19)0.060 (2)0.0411 (16)0.0026 (15)0.0117 (14)0.0019 (14)
C20.0465 (19)0.079 (3)0.071 (2)0.0047 (18)0.0117 (16)0.008 (2)
C30.056 (2)0.103 (3)0.067 (2)0.019 (2)0.0107 (18)0.005 (2)
C40.078 (3)0.072 (3)0.065 (2)0.025 (2)0.0116 (19)0.0026 (19)
C50.068 (2)0.058 (2)0.0457 (17)0.0094 (17)0.0114 (15)0.0038 (15)
C60.093 (3)0.048 (2)0.061 (2)0.0015 (19)0.012 (2)0.0008 (16)
C70.084 (3)0.052 (2)0.069 (2)0.0125 (19)0.016 (2)0.0065 (17)
C80.059 (2)0.065 (2)0.0513 (19)0.0093 (17)0.0123 (15)0.0004 (16)
C90.0483 (17)0.0534 (19)0.0397 (16)0.0027 (14)0.0097 (13)0.0010 (13)
C100.064 (2)0.0467 (18)0.058 (2)0.0106 (15)0.0246 (17)0.0076 (14)
C110.067 (2)0.058 (2)0.092 (3)0.0124 (17)0.029 (2)0.013 (2)
C120.092 (3)0.078 (3)0.088 (3)0.024 (2)0.056 (3)0.015 (2)
C130.121 (4)0.069 (3)0.067 (3)0.017 (3)0.038 (3)0.001 (2)
C140.106 (3)0.057 (2)0.054 (2)0.006 (2)0.030 (2)0.0017 (17)
C150.118 (4)0.084 (3)0.052 (2)0.006 (3)0.011 (2)0.016 (2)
C160.094 (3)0.105 (3)0.061 (2)0.021 (3)0.001 (2)0.020 (2)
C170.070 (2)0.083 (3)0.060 (2)0.012 (2)0.0052 (18)0.0055 (19)
C180.071 (2)0.0466 (18)0.0475 (17)0.0031 (16)0.0168 (16)0.0022 (14)
C190.0482 (17)0.0507 (18)0.0548 (19)0.0019 (14)0.0157 (14)0.0001 (15)
C200.058 (2)0.0489 (19)0.076 (2)0.0013 (16)0.0149 (17)0.0003 (17)
C210.065 (2)0.064 (2)0.074 (3)0.0027 (18)0.0116 (18)0.025 (2)
C220.067 (2)0.077 (3)0.053 (2)0.0019 (19)0.0104 (17)0.0129 (18)
C230.0515 (18)0.062 (2)0.0467 (17)0.0016 (15)0.0119 (14)0.0048 (15)
C240.069 (2)0.077 (2)0.0429 (17)0.0066 (19)0.0080 (16)0.0067 (18)
C250.075 (2)0.060 (2)0.0505 (19)0.0037 (18)0.0112 (17)0.0127 (17)
C260.066 (2)0.0477 (18)0.0513 (19)0.0011 (15)0.0141 (15)0.0029 (15)
C270.0438 (16)0.0526 (19)0.0483 (17)0.0012 (14)0.0134 (13)0.0007 (14)
C280.58 (3)0.232 (17)0.31 (2)0.02 (2)0.29 (2)0.054 (15)
Geometric parameters (Å, º) top
Ni1—O11.901 (2)C8—H80.93
Ni1—O21.906 (2)C10—C111.383 (5)
Ni1—O31.895 (2)C10—C181.415 (5)
Ni1—N11.923 (3)C11—C121.423 (6)
Ni1—N21.923 (3)C11—H110.93
Ni1—N31.935 (3)C12—C131.355 (6)
O1—C11.309 (4)C12—H120.93
O2—C101.324 (4)C13—C141.404 (6)
O2—H2A0.93C13—H130.93
O3—C191.321 (4)C14—C181.406 (5)
O4—H4A0.904 (10)C14—C151.411 (6)
O4—H4B0.865 (10)C15—C161.332 (6)
O5—C281.228 (13)C15—H150.93
N1—C81.339 (4)C16—C171.397 (5)
N1—C91.363 (4)C16—H160.93
N2—C171.318 (4)C17—H170.93
N2—C181.367 (4)C19—C201.383 (4)
N3—C261.323 (4)C19—C271.416 (4)
N3—C271.366 (4)C20—C211.408 (5)
C1—C21.393 (4)C20—H200.93
C1—C91.425 (4)C21—C221.363 (5)
C2—C31.399 (5)C21—H210.93
C2—H20.93C22—C231.406 (5)
C3—C41.355 (6)C22—H220.93
C3—H30.93C23—C241.411 (5)
C4—C51.423 (5)C23—C271.415 (4)
C4—H40.93C24—C251.357 (5)
C5—C91.411 (5)C24—H240.93
C5—C61.418 (5)C25—C261.396 (4)
C6—C71.350 (5)C25—H250.93
C6—H60.93C26—H260.93
C7—C81.408 (5)C28—C28i1.29 (3)
C7—H70.93C28—H280.93
O1—Ni1—O2177.14 (9)O2—C10—C11124.8 (3)
O1—Ni1—O390.12 (9)O2—C10—C18117.5 (3)
O2—Ni1—O391.94 (10)C11—C10—C18117.6 (3)
O1—Ni1—N185.26 (10)C10—C11—C12118.7 (4)
O1—Ni1—N292.48 (10)C10—C11—H11120.7
O1—Ni1—N391.56 (10)C12—C11—H11120.7
O2—Ni1—N192.66 (10)C13—C12—C11123.3 (4)
O2—Ni1—N285.62 (10)C13—C12—H12118.4
O2—Ni1—N390.57 (10)C11—C12—H12118.4
O3—Ni1—N1175.36 (10)C12—C13—C14119.7 (4)
O3—Ni1—N287.60 (11)C12—C13—H13120.2
O3—Ni1—N385.93 (10)C14—C13—H13120.2
N1—Ni1—N292.18 (11)C13—C14—C18117.4 (4)
N1—Ni1—N394.59 (11)C13—C14—C15126.3 (4)
N2—Ni1—N3172.38 (11)C18—C14—C15116.3 (4)
C1—O1—Ni1111.99 (19)C16—C15—C14120.7 (4)
C10—O2—Ni1111.4 (2)C16—C15—H15119.7
C10—O2—H2A124.3C14—C15—H15119.7
Ni1—O2—H2A124.3C15—C16—C17120.4 (4)
C19—O3—Ni1111.50 (19)C15—C16—H16119.8
H4A—O4—H4B98 (2)C17—C16—H16119.8
C8—N1—C9119.0 (3)N2—C17—C16121.1 (4)
C8—N1—Ni1130.0 (2)N2—C17—H17119.4
C9—N1—Ni1111.0 (2)C16—C17—H17119.4
C17—N2—C18119.6 (3)N2—C18—C14121.8 (3)
C17—N2—Ni1129.7 (2)N2—C18—C10114.8 (3)
C18—N2—Ni1110.6 (2)C14—C18—C10123.4 (3)
C26—N3—C27119.1 (3)O3—C19—C20124.5 (3)
C26—N3—Ni1131.3 (2)O3—C19—C27117.4 (3)
C27—N3—Ni1109.7 (2)C20—C19—C27118.0 (3)
O1—C1—C2125.8 (3)C19—C20—C21119.4 (3)
O1—C1—C9117.5 (3)C19—C20—H20120.3
C2—C1—C9116.6 (3)C21—C20—H20120.3
C1—C2—C3120.5 (3)C22—C21—C20122.9 (3)
C1—C2—H2119.7C22—C21—H21118.5
C3—C2—H2119.7C20—C21—H21118.5
C4—C3—C2122.9 (4)C21—C22—C23119.5 (3)
C4—C3—H3118.6C21—C22—H22120.3
C2—C3—H3118.6C23—C22—H22120.3
C3—C4—C5119.5 (4)C22—C23—C24125.5 (3)
C3—C4—H4120.3C22—C23—C27117.9 (3)
C5—C4—H4120.3C24—C23—C27116.5 (3)
C9—C5—C6116.0 (3)C25—C24—C23119.8 (3)
C9—C5—C4117.6 (3)C25—C24—H24120.1
C6—C5—C4126.4 (3)C23—C24—H24120.1
C7—C6—C5120.7 (3)C24—C25—C26120.6 (3)
C7—C6—H6119.6C24—C25—H25119.7
C5—C6—H6119.6C26—C25—H25119.7
C6—C7—C8120.0 (3)N3—C26—C25121.6 (3)
C6—C7—H7120.0N3—C26—H26119.2
C8—C7—H7120.0C25—C26—H26119.2
N1—C8—C7121.3 (3)N3—C27—C23122.5 (3)
N1—C8—H8119.4N3—C27—C19115.3 (3)
C7—C8—H8119.4C23—C27—C19122.2 (3)
N1—C9—C5123.0 (3)O5—C28—C28i127 (2)
N1—C9—C1114.2 (3)O5—C28—H28116.5
C5—C9—C1122.8 (3)C28i—C28—H28116.5
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···O50.87 (1)1.72 (3)2.302 (17)123 (2)
O2—H2A···O4ii0.932.112.888 (8)140
Symmetry code: (ii) x+1/2, y+3/2, z+1/2.
 

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