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metal-organic compounds
Bis(methanol-κO)bis(quinoline-2-carboxylato-κ2N,O)nickel(II)
aDepartment of Fine Chemistry, Seoul National University of Science and Technology, Seoul 139-743, Republic of Korea, bDepartment of Forest Genetic Resources, Korea Forest Research Institute, Suwon 441-847, Republic of Korea, cDepartment of Forest & Environment Resources, Kyungpook National University, Sangju 742-711, Republic of Korea, and dDeaprtment of Chemistry and Nano Science, Ewha Womans University, Seoul 120-750, Republic of Korea
*Correspondence e-mail: chealkim@sunt.ac.kr, ymeekim@ewha.ac.kr
In the title complex, [Ni(C10H6NO2)2(CH3OH)2], the NiII ion lies on an inversion center and is coordinated by two quinoline-2-carboxylate ligands in the equatorial sites and two axial methanol ligands, forming a distorted octahedral environment. In the crystal, molecules are linked via O—H⋯O hydrogen bonds into a two-dimensional network parallel to (10).
Related literature
For interactions of metal ions with amino acids, see: Daniele et al. (2008); Parkin (2004
); Tshuva & Lippard (2004
); Stoumpos et al. (2009
). For related structures, see: Lee et al. (2008
); Park et al. (2008
); Shin et al. (2009
); Song et al. (2009
); Yu et al. (2008
, 2009
, 2010
); Kim et al. (2011
).
Experimental
Crystal data
|
Refinement
|
|
Data collection: SMART (Bruker, 1997); cell SAINT (Bruker, 1997
); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008
); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008
); molecular graphics: SHELXTL (Sheldrick, 2008
); software used to prepare material for publication: SHELXTL.
Supporting information
10.1107/S1600536811041134/lh5343sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536811041134/lh5343Isup2.hkl
Quinaldic acid (17.7 mg, 0.1 mmol) and NH4OH (13.9 ml, 0.1 mmol) were dissolved in 4 ml methanol and carefully layered with 4 ml methanol solution of nickel(II) chloride hexahydrate (11.9 mg, 0.05 mmol). Suitable crystals of the title compound for X-ray analysis were obtained in two weeks.
H atoms bonded to C atoms were placed in calculated positions with C—H distances of 0.93-0.96Å. They were included in the
in a riding-motion approximation with Uiso(H)= 1.2Ueq(C) or Uiso(H) = 1.5Ueq(Cmethyl). The positions of O—H atoms of the methanol ligands were refined with O—H restraints (0.86 Å) and Uiso(H)= 1.2Ueq(O).Data collection: SMART (Bruker, 1997); cell
SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008). ![]() | Fig. 1. The molecular structure of the title compound with displacement ellipsoids shown at the 30% probability level. Unlabeled atoms are related by the symmetry operator (-x+2, -y, -z+1). |
[Ni(C10H6NO2)2(CH4O)2] | F(000) = 484 |
Mr = 467.11 | Dx = 1.569 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 3640 reflections |
a = 10.411 (2) Å | θ = 2.6–28.1° |
b = 7.3910 (15) Å | µ = 1.03 mm−1 |
c = 13.556 (3) Å | T = 293 K |
β = 108.57 (3)° | Rod, colorless |
V = 988.8 (3) Å3 | 0.40 × 0.10 × 0.10 mm |
Z = 2 |
Bruker SMART CCD area-detector diffractometer | 1929 independent reflections |
Radiation source: fine-focus sealed tube | 1666 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.018 |
ϕ and ω scans | θmax = 26.0°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −12→12 |
Tmin = 0.884, Tmax = 0.903 | k = −9→9 |
5292 measured reflections | l = −9→16 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.027 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.076 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0451P)2 + 0.2296P] where P = (Fo2 + 2Fc2)/3 |
1929 reflections | (Δ/σ)max = 0.001 |
146 parameters | Δρmax = 0.22 e Å−3 |
1 restraint | Δρmin = −0.31 e Å−3 |
[Ni(C10H6NO2)2(CH4O)2] | V = 988.8 (3) Å3 |
Mr = 467.11 | Z = 2 |
Monoclinic, P21/n | Mo Kα radiation |
a = 10.411 (2) Å | µ = 1.03 mm−1 |
b = 7.3910 (15) Å | T = 293 K |
c = 13.556 (3) Å | 0.40 × 0.10 × 0.10 mm |
β = 108.57 (3)° |
Bruker SMART CCD area-detector diffractometer | 1929 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | 1666 reflections with I > 2σ(I) |
Tmin = 0.884, Tmax = 0.903 | Rint = 0.018 |
5292 measured reflections |
R[F2 > 2σ(F2)] = 0.027 | 1 restraint |
wR(F2) = 0.076 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | Δρmax = 0.22 e Å−3 |
1929 reflections | Δρmin = −0.31 e Å−3 |
146 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Ni1 | 1.0000 | 0.0000 | 0.5000 | 0.02463 (12) | |
N1 | 0.79816 (13) | 0.10618 (19) | 0.48009 (11) | 0.0270 (3) | |
O1 | 0.94209 (12) | 0.07175 (19) | 0.35013 (9) | 0.0314 (3) | |
O2 | 0.78467 (15) | 0.2090 (2) | 0.22280 (11) | 0.0530 (4) | |
O3 | 0.91781 (13) | −0.25715 (18) | 0.45429 (10) | 0.0362 (3) | |
H3O | 0.8599 (16) | −0.259 (3) | 0.3928 (7) | 0.043* | |
C1 | 0.72490 (17) | 0.1223 (2) | 0.54860 (13) | 0.0296 (4) | |
C2 | 0.77500 (19) | 0.0457 (3) | 0.64897 (15) | 0.0360 (4) | |
H2 | 0.8589 | −0.0116 | 0.6698 | 0.043* | |
C3 | 0.7003 (2) | 0.0554 (3) | 0.71576 (16) | 0.0427 (5) | |
H3 | 0.7331 | 0.0020 | 0.7811 | 0.051* | |
C4 | 0.5748 (2) | 0.1451 (3) | 0.68685 (17) | 0.0453 (5) | |
H4 | 0.5257 | 0.1514 | 0.7333 | 0.054* | |
C5 | 0.5250 (2) | 0.2221 (3) | 0.59184 (17) | 0.0429 (5) | |
H5 | 0.4425 | 0.2826 | 0.5740 | 0.051* | |
C6 | 0.59717 (18) | 0.2118 (2) | 0.51872 (15) | 0.0347 (4) | |
C7 | 0.54761 (19) | 0.2841 (3) | 0.41796 (17) | 0.0414 (5) | |
H7 | 0.4653 | 0.3455 | 0.3971 | 0.050* | |
C8 | 0.61990 (19) | 0.2645 (3) | 0.35068 (15) | 0.0385 (4) | |
H8 | 0.5871 | 0.3101 | 0.2833 | 0.046* | |
C9 | 0.74535 (17) | 0.1737 (2) | 0.38513 (14) | 0.0300 (4) | |
C10 | 0.82890 (17) | 0.1504 (3) | 0.31228 (14) | 0.0315 (4) | |
C11 | 0.8677 (2) | −0.3714 (3) | 0.51879 (17) | 0.0481 (5) | |
H11A | 0.9424 | −0.4196 | 0.5740 | 0.072* | |
H11B | 0.8167 | −0.4690 | 0.4779 | 0.072* | |
H11C | 0.8102 | −0.3025 | 0.5478 | 0.072* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.02223 (18) | 0.03058 (19) | 0.01837 (18) | 0.00163 (12) | 0.00265 (12) | −0.00029 (12) |
N1 | 0.0236 (7) | 0.0301 (8) | 0.0250 (7) | 0.0008 (6) | 0.0045 (6) | −0.0006 (6) |
O1 | 0.0268 (6) | 0.0448 (7) | 0.0206 (6) | 0.0047 (6) | 0.0045 (5) | 0.0017 (6) |
O2 | 0.0390 (7) | 0.0871 (12) | 0.0295 (7) | 0.0141 (8) | 0.0060 (6) | 0.0189 (8) |
O3 | 0.0352 (7) | 0.0369 (7) | 0.0291 (7) | −0.0050 (6) | 0.0000 (5) | −0.0025 (6) |
C1 | 0.0267 (8) | 0.0299 (9) | 0.0320 (10) | −0.0015 (7) | 0.0089 (7) | −0.0048 (7) |
C2 | 0.0307 (9) | 0.0458 (11) | 0.0317 (10) | 0.0052 (8) | 0.0105 (8) | −0.0009 (8) |
C3 | 0.0430 (11) | 0.0562 (12) | 0.0317 (10) | 0.0024 (10) | 0.0158 (9) | −0.0019 (9) |
C4 | 0.0414 (11) | 0.0561 (13) | 0.0459 (12) | −0.0013 (10) | 0.0246 (10) | −0.0108 (10) |
C5 | 0.0323 (10) | 0.0456 (12) | 0.0539 (13) | 0.0064 (9) | 0.0182 (9) | −0.0057 (10) |
C6 | 0.0292 (9) | 0.0328 (10) | 0.0419 (11) | 0.0019 (8) | 0.0110 (8) | −0.0035 (8) |
C7 | 0.0288 (9) | 0.0418 (11) | 0.0511 (12) | 0.0112 (8) | 0.0094 (9) | 0.0063 (9) |
C8 | 0.0304 (9) | 0.0429 (11) | 0.0366 (10) | 0.0061 (8) | 0.0027 (8) | 0.0114 (9) |
C9 | 0.0249 (8) | 0.0317 (9) | 0.0302 (9) | −0.0013 (7) | 0.0043 (7) | 0.0015 (8) |
C10 | 0.0275 (8) | 0.0384 (10) | 0.0241 (9) | −0.0002 (8) | 0.0017 (7) | 0.0025 (8) |
C11 | 0.0544 (13) | 0.0428 (12) | 0.0447 (12) | −0.0066 (10) | 0.0124 (10) | 0.0000 (10) |
Ni1—O1i | 1.9979 (12) | C3—C4 | 1.405 (3) |
Ni1—O1 | 1.9980 (12) | C3—H3 | 0.9300 |
Ni1—O3i | 2.0954 (13) | C4—C5 | 1.351 (3) |
Ni1—O3 | 2.0954 (13) | C4—H4 | 0.9300 |
Ni1—N1 | 2.1779 (14) | C5—C6 | 1.423 (3) |
Ni1—N1i | 2.1779 (14) | C5—H5 | 0.9300 |
N1—C9 | 1.326 (2) | C6—C7 | 1.403 (3) |
N1—C1 | 1.382 (2) | C7—C8 | 1.363 (3) |
O1—C10 | 1.267 (2) | C7—H7 | 0.9300 |
O2—C10 | 1.231 (2) | C8—C9 | 1.409 (3) |
O3—C11 | 1.429 (3) | C8—H8 | 0.9300 |
O3—H3O | 0.859 (2) | C9—C10 | 1.519 (3) |
C1—C2 | 1.411 (3) | C11—H11A | 0.9600 |
C1—C6 | 1.424 (2) | C11—H11B | 0.9600 |
C2—C3 | 1.371 (3) | C11—H11C | 0.9600 |
C2—H2 | 0.9300 | ||
O1i—Ni1—O1 | 180.0 | C2—C3—H3 | 119.5 |
O1i—Ni1—O3i | 88.71 (6) | C4—C3—H3 | 119.5 |
O1—Ni1—O3i | 91.29 (6) | C5—C4—C3 | 120.31 (19) |
O1i—Ni1—O3 | 91.29 (6) | C5—C4—H4 | 119.8 |
O1—Ni1—O3 | 88.71 (6) | C3—C4—H4 | 119.8 |
O3i—Ni1—O3 | 180.00 (7) | C4—C5—C6 | 120.93 (18) |
O1i—Ni1—N1 | 100.86 (6) | C4—C5—H5 | 119.5 |
O1—Ni1—N1 | 79.14 (6) | C6—C5—H5 | 119.5 |
O3i—Ni1—N1 | 89.82 (5) | C7—C6—C5 | 123.07 (17) |
O3—Ni1—N1 | 90.18 (5) | C7—C6—C1 | 118.33 (17) |
O1i—Ni1—N1i | 79.14 (6) | C5—C6—C1 | 118.60 (17) |
O1—Ni1—N1i | 100.86 (6) | C8—C7—C6 | 120.06 (17) |
O3i—Ni1—N1i | 90.18 (5) | C8—C7—H7 | 120.0 |
O3—Ni1—N1i | 89.82 (5) | C6—C7—H7 | 120.0 |
N1—Ni1—N1i | 180.0 | C7—C8—C9 | 118.69 (18) |
C9—N1—C1 | 118.24 (14) | C7—C8—H8 | 120.7 |
C9—N1—Ni1 | 109.96 (11) | C9—C8—H8 | 120.7 |
C1—N1—Ni1 | 131.69 (11) | N1—C9—C8 | 123.71 (17) |
C10—O1—Ni1 | 118.31 (11) | N1—C9—C10 | 116.25 (15) |
C11—O3—Ni1 | 123.34 (12) | C8—C9—C10 | 120.04 (16) |
C11—O3—H3O | 107.6 (15) | O2—C10—O1 | 124.64 (18) |
Ni1—O3—H3O | 113.5 (15) | O2—C10—C9 | 119.26 (16) |
N1—C1—C2 | 119.98 (15) | O1—C10—C9 | 116.09 (15) |
N1—C1—C6 | 120.95 (16) | O3—C11—H11A | 109.5 |
C2—C1—C6 | 119.06 (17) | O3—C11—H11B | 109.5 |
C3—C2—C1 | 120.16 (18) | H11A—C11—H11B | 109.5 |
C3—C2—H2 | 119.9 | O3—C11—H11C | 109.5 |
C1—C2—H2 | 119.9 | H11A—C11—H11C | 109.5 |
C2—C3—C4 | 120.9 (2) | H11B—C11—H11C | 109.5 |
O1i—Ni1—N1—C9 | 175.65 (12) | C2—C3—C4—C5 | 0.6 (3) |
O1—Ni1—N1—C9 | −4.35 (12) | C3—C4—C5—C6 | 1.0 (3) |
O3i—Ni1—N1—C9 | 87.00 (12) | C4—C5—C6—C7 | 177.7 (2) |
O3—Ni1—N1—C9 | −93.00 (12) | C4—C5—C6—C1 | −1.5 (3) |
O1i—Ni1—N1—C1 | −0.27 (16) | N1—C1—C6—C7 | −0.3 (3) |
O1—Ni1—N1—C1 | 179.73 (16) | C2—C1—C6—C7 | −178.75 (18) |
O3i—Ni1—N1—C1 | −88.92 (15) | N1—C1—C6—C5 | 179.02 (16) |
O3—Ni1—N1—C1 | 91.08 (15) | C2—C1—C6—C5 | 0.5 (3) |
O3i—Ni1—O1—C10 | −85.58 (14) | C5—C6—C7—C8 | −177.88 (19) |
O3—Ni1—O1—C10 | 94.42 (14) | C1—C6—C7—C8 | 1.4 (3) |
N1—Ni1—O1—C10 | 3.98 (13) | C6—C7—C8—C9 | −1.1 (3) |
N1i—Ni1—O1—C10 | −176.02 (13) | C1—N1—C9—C8 | 1.4 (3) |
O1i—Ni1—O3—C11 | 27.49 (15) | Ni1—N1—C9—C8 | −175.15 (15) |
O1—Ni1—O3—C11 | −152.51 (15) | C1—N1—C9—C10 | −179.23 (14) |
N1—Ni1—O3—C11 | −73.38 (15) | Ni1—N1—C9—C10 | 4.23 (18) |
N1i—Ni1—O3—C11 | 106.62 (15) | C7—C8—C9—N1 | −0.3 (3) |
C9—N1—C1—C2 | 177.39 (17) | C7—C8—C9—C10 | −179.64 (18) |
Ni1—N1—C1—C2 | −7.0 (2) | Ni1—O1—C10—O2 | 176.36 (16) |
C9—N1—C1—C6 | −1.1 (2) | Ni1—O1—C10—C9 | −2.9 (2) |
Ni1—N1—C1—C6 | 174.56 (12) | N1—C9—C10—O2 | 179.42 (18) |
N1—C1—C2—C3 | −177.54 (18) | C8—C9—C10—O2 | −1.2 (3) |
C6—C1—C2—C3 | 1.0 (3) | N1—C9—C10—O1 | −1.3 (2) |
C1—C2—C3—C4 | −1.5 (3) | C8—C9—C10—O1 | 178.12 (17) |
Symmetry code: (i) −x+2, −y, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3O···O2ii | 0.86 (1) | 1.81 (1) | 2.655 (2) | 167 (2) |
Symmetry code: (ii) −x+3/2, y−1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [Ni(C10H6NO2)2(CH4O)2] |
Mr | 467.11 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 10.411 (2), 7.3910 (15), 13.556 (3) |
β (°) | 108.57 (3) |
V (Å3) | 988.8 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.03 |
Crystal size (mm) | 0.40 × 0.10 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 1997) |
Tmin, Tmax | 0.884, 0.903 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5292, 1929, 1666 |
Rint | 0.018 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.027, 0.076, 1.07 |
No. of reflections | 1929 |
No. of parameters | 146 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.22, −0.31 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3O···O2i | 0.859 (11) | 1.810 (12) | 2.655 (2) | 167.2 (18) |
Symmetry code: (i) −x+3/2, y−1/2, −z+1/2. |
Acknowledgements
Financial support from the Forest Science & Technology Projects (S121011L080120) and the Cooperative Research Program for Agricultural Science & Technology Developments (20070301–036-019–02) is gratefully acknowledged.
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The interaction of transition metal ions with biologically active molecules such as amino acids, proteins, sugars, and various acids is of great importance in biological systems (Daniele, et al., 2008; Parkin, 2004; Tshuva & Lippard, 2004; Stoumpos, et al., 2009). As models to examine the interaction, we have intensively studied the interaction of transition metal ions with various acids such as benzoic acid, fulvic acids and humic acids and have reported a variety of structures of copper(II), cadmium(II), and zinc(II) benzoates with quinoxaline,6-methylquinoline, 3-methylquinoline, trans-1-(2-pyridyl)-2-(4-pyridyl)ethylene, and di-2-pyridyl ketone (Lee, et al., 2008; Yu, et al., 2008; Park, et al., 2008; Shin, et al., 2009; Song, et al., 2009; Yu, et al., 2008,2009,2010; Kim, et al., 2011). In this work, we have employed nickel(II) chloride as a building block and quinaldic acid as a ligand. We report herin the structure of the title complex.
In the crystal structure of the title compound, [Ni(C10H6NO2)2(CH3OH)2], the NiII ion occupies a crystallographic inversion center. Two quinoline-2-carboxylate ligands coordinate the NiII ion in the equatorial sites and two methanol ligands coordinate the NiII ion in axial sites to form a distorted octahedral environment (Fig. 1). In the crystal, molecules are linked via O—H···O hydrogen bonds to form a two-dimensional network parallel to [1 0 -1].