metal-organic compounds
(Di-2-pyridylamine-κ2N1,N1′)bis(methacrylato-κO)nickel(II) sesquihydrate
aDepartment of Chemistry and Chemical Engineering, Daqing Normal University, 163712 Daqing, Heilongjiang, People's Republic of China, bThe No. 4 Middle School of Liaocheng, 252000 Liaocheng, Shandong, People's Republic of China, and cTaishan University, 271021 Taian, Shandong, People's Republic of China
*Correspondence e-mail: klsz79@163.com
In the title mononuclear complex, [Ni(C4H5O2)2(C10H9N3)]·1.5H2O, the NiII ion is in a distorted square-planar coordination environment, formed by two O atoms from two methacrylate ligands and two N atoms from a bis-chelating dipyridylamine ligand. In the intermolecular O—H⋯O and N—H⋯O hydrogen bonds link complex molecules and water molecules into one-dimensional chains.
Related literature
For the Cu analog of the title compound, see: Liu, et al. (2006). For related literature, see: Carabias-Martínez et al. (2006); Matsui et al. (1997); Wang et al. (1997); Wu et al. (2002).
Experimental
Crystal data
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Refinement
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Data collection: SMART (Bruker, 1996); cell SAINT (Bruker, 1996); 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/S1600536808009008/lh2600sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808009008/lh2600Isup2.hkl
Methacrylic acid and dipyridin-2-ylamine are commercially available, and they were used without further purification. The reaction was carried out under an air atmoshpere. Methacrylic acid (2 mmol), dipyridin-2-ylamine (1 mmol) and nickel(II)chloride (1 mmol) were added to water and the mixture was stirred for 4 h at 323 K. After cooling to room temperature, the solution was filtered. The solvent was removed from the filtrate under vacuum, and the solid residue was recrystallized from ethanol to form yellow crystals which were suitable for X-Ray diffraction study. Yield, 78%. m.p. 547 K. Analysis, calculated for C18H22N3NiO5.50: C 50.62, H 5.19, N 9.84; found: C 50.38, H 5.43, N 9.52. The elemental analyses were performed with a Perkine Elemer PE2400II instrument.
Methyl H atoms were included in calculated positions with C—H = 0.96Å and Uiso(H) = 1.5Ueq(C). H atoms bonded to N3 and O6 were included in calculations with N—H = 0.6 Å, O—H = 0.85Å and Uiso(H) = 1.2Ueq(O,N). All other H atoms were refined independently with isotropic displacement parameters. The C—H distances refined to 0.90 (3) - 1.01 (3) Å.
Data collection: SMART (Bruker, 1996); cell
SAINT (Bruker, 1996); data reduction: SAINT (Bruker, 1996); 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).[Ni(C4H5O2)2(C10H9N3)]·1.5H2O | F(000) = 892 |
Mr = 427.10 | Dx = 1.416 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 4631 reflections |
a = 8.3686 (9) Å | θ = 1.9–28.3° |
b = 15.7235 (16) Å | µ = 1.00 mm−1 |
c = 15.5396 (17) Å | T = 293 K |
β = 101.483 (2)° | Block, blue |
V = 2003.8 (4) Å3 | 0.29 × 0.22 × 0.18 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 3512 independent reflections |
Radiation source: fine-focus sealed tube | 2720 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.077 |
ϕ and ω scans | θmax = 25.0°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→9 |
Tmin = 0.740, Tmax = 0.872 | k = −18→17 |
9960 measured reflections | l = −15→18 |
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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.084 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | w = 1/[σ2(Fo2) + (0.03P)2] where P = (Fo2 + 2Fc2)/3 |
3512 reflections | (Δ/σ)max = 0.013 |
311 parameters | Δρmax = 0.32 e Å−3 |
13 restraints | Δρmin = −0.24 e Å−3 |
[Ni(C4H5O2)2(C10H9N3)]·1.5H2O | V = 2003.8 (4) Å3 |
Mr = 427.10 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 8.3686 (9) Å | µ = 1.00 mm−1 |
b = 15.7235 (16) Å | T = 293 K |
c = 15.5396 (17) Å | 0.29 × 0.22 × 0.18 mm |
β = 101.483 (2)° |
Bruker SMART CCD area-detector diffractometer | 3512 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2720 reflections with I > 2σ(I) |
Tmin = 0.740, Tmax = 0.872 | Rint = 0.077 |
9960 measured reflections |
R[F2 > 2σ(F2)] = 0.036 | 13 restraints |
wR(F2) = 0.084 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | Δρmax = 0.32 e Å−3 |
3512 reflections | Δρmin = −0.24 e Å−3 |
311 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 | Occ. (<1) | |
Ni1 | 0.71669 (3) | 0.166235 (18) | 0.635377 (19) | 0.05233 (13) | |
O1 | 0.6953 (2) | 0.18663 (11) | 0.75859 (11) | 0.0676 (5) | |
O2 | 0.4520 (2) | 0.16405 (13) | 0.68304 (14) | 0.0869 (6) | |
O3 | 0.6959 (2) | 0.28811 (11) | 0.60684 (13) | 0.0744 (5) | |
O4 | 0.9584 (2) | 0.26650 (12) | 0.62783 (14) | 0.0866 (6) | |
O5 | 0.1555 (3) | 0.13886 (13) | 0.58041 (14) | 0.0871 (6) | |
O6 | 0.1576 (18) | 0.8401 (6) | 0.9099 (9) | 0.365 (9) | 0.50 |
H6A | 0.2379 | 0.8070 | 0.9103 | 0.437* | 0.50 |
H6B | 0.0724 | 0.8139 | 0.8846 | 0.437* | 0.50 |
N1 | 0.8388 (2) | 0.05866 (11) | 0.66380 (12) | 0.0554 (5) | |
N2 | 0.6341 (2) | 0.13116 (12) | 0.51218 (13) | 0.0555 (5) | |
N3 | 0.7837 (2) | 0.00393 (12) | 0.51996 (13) | 0.0599 (5) | |
H19 | 0.8113 | −0.0357 | 0.4877 | 0.072* | |
C1 | 0.9209 (4) | 0.0486 (2) | 0.74736 (19) | 0.0786 (8) | |
C2 | 1.0198 (4) | −0.0173 (2) | 0.7755 (2) | 0.0922 (10) | |
C3 | 1.0384 (4) | −0.0799 (2) | 0.7157 (2) | 0.0857 (9) | |
C4 | 0.9597 (3) | −0.07131 (17) | 0.63130 (19) | 0.0682 (7) | |
C5 | 0.8605 (3) | −0.00130 (14) | 0.60641 (16) | 0.0530 (6) | |
C6 | 0.6718 (3) | 0.05967 (14) | 0.47463 (15) | 0.0514 (5) | |
C7 | 0.5986 (3) | 0.03930 (18) | 0.38840 (17) | 0.0659 (7) | |
C8 | 0.4874 (4) | 0.0926 (2) | 0.34175 (19) | 0.0745 (8) | |
C9 | 0.4470 (4) | 0.1665 (2) | 0.38006 (19) | 0.0724 (8) | |
C10 | 0.5214 (3) | 0.18320 (18) | 0.4632 (2) | 0.0693 (7) | |
C11 | 0.5437 (3) | 0.18002 (14) | 0.75381 (19) | 0.0612 (7) | |
C12 | 0.4763 (4) | 0.18975 (16) | 0.8346 (2) | 0.0745 (8) | |
C13 | 0.5788 (7) | 0.1974 (2) | 0.9112 (3) | 0.1023 (12) | |
C14 | 0.3001 (5) | 0.1899 (3) | 0.8252 (3) | 0.1299 (14) | |
H13 | 0.2721 | 0.2052 | 0.8801 | 0.195* | |
H11 | 0.2583 | 0.1342 | 0.8081 | 0.195* | |
H12 | 0.2534 | 0.2304 | 0.7810 | 0.195* | |
C15 | 0.8403 (4) | 0.31425 (16) | 0.60955 (16) | 0.0606 (6) | |
C16 | 0.8616 (4) | 0.40609 (18) | 0.58992 (18) | 0.0745 (7) | |
C17 | 1.0179 (7) | 0.4399 (3) | 0.6099 (3) | 0.1124 (13) | |
C18 | 0.7233 (5) | 0.4528 (2) | 0.5499 (3) | 0.1287 (14) | |
H17 | 0.7563 | 0.5083 | 0.5343 | 0.193* | |
H18 | 0.6504 | 0.4584 | 0.5901 | 0.193* | |
H16 | 0.6688 | 0.4237 | 0.4980 | 0.193* | |
H1 | 0.913 (3) | 0.0917 (18) | 0.7842 (18) | 0.083 (9)* | |
H2 | 1.086 (3) | −0.0193 (18) | 0.8329 (14) | 0.099 (10)* | |
H3 | 1.108 (4) | −0.131 (2) | 0.733 (2) | 0.117 (11)* | |
H4 | 0.964 (3) | −0.1118 (14) | 0.5870 (14) | 0.066 (7)* | |
H5 | 0.630 (2) | −0.0103 (11) | 0.3650 (14) | 0.058 (7)* | |
H6 | 0.430 (3) | 0.0750 (19) | 0.281 (2) | 0.106 (10)* | |
H7 | 0.373 (3) | 0.2059 (16) | 0.3503 (17) | 0.076 (8)* | |
H8 | 0.495 (3) | 0.2368 (17) | 0.4916 (17) | 0.084 (8)* | |
H9 | 0.690 (2) | 0.187 (2) | 0.919 (2) | 0.118 (16)* | |
H10 | 0.523 (5) | 0.207 (2) | 0.958 (3) | 0.153 (15)* | |
H14 | 1.099 (4) | 0.403 (2) | 0.633 (2) | 0.133 (17)* | |
H15 | 1.031 (4) | 0.4937 (15) | 0.592 (2) | 0.134 (14)* | |
H20 | 0.257 (3) | 0.1554 (17) | 0.6173 (18) | 0.099 (11)* | |
H21 | 0.082 (4) | 0.1753 (18) | 0.598 (2) | 0.128 (14)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.0512 (2) | 0.0530 (2) | 0.0534 (2) | 0.00317 (13) | 0.01212 (15) | −0.00762 (14) |
O1 | 0.0629 (12) | 0.0792 (12) | 0.0624 (11) | −0.0013 (9) | 0.0162 (9) | −0.0175 (9) |
O2 | 0.0608 (12) | 0.1171 (17) | 0.0832 (14) | −0.0144 (11) | 0.0152 (11) | −0.0286 (12) |
O3 | 0.0689 (12) | 0.0613 (11) | 0.0941 (13) | 0.0041 (9) | 0.0191 (10) | −0.0042 (10) |
O4 | 0.0766 (13) | 0.0790 (13) | 0.1072 (16) | 0.0182 (10) | 0.0254 (12) | 0.0057 (11) |
O5 | 0.0704 (13) | 0.0955 (14) | 0.0905 (15) | 0.0182 (11) | 0.0041 (12) | −0.0320 (12) |
O6 | 0.410 (19) | 0.215 (11) | 0.395 (19) | −0.049 (10) | −0.096 (16) | 0.069 (10) |
N1 | 0.0556 (12) | 0.0580 (12) | 0.0519 (11) | 0.0019 (9) | 0.0089 (10) | −0.0038 (9) |
N2 | 0.0527 (12) | 0.0598 (12) | 0.0546 (12) | 0.0037 (10) | 0.0121 (10) | 0.0011 (10) |
N3 | 0.0686 (13) | 0.0582 (12) | 0.0528 (12) | 0.0107 (10) | 0.0121 (10) | −0.0075 (10) |
C1 | 0.084 (2) | 0.086 (2) | 0.0597 (18) | 0.0167 (17) | −0.0003 (15) | −0.0109 (16) |
C2 | 0.096 (2) | 0.105 (2) | 0.0633 (19) | 0.030 (2) | −0.0122 (18) | −0.0020 (18) |
C3 | 0.088 (2) | 0.078 (2) | 0.084 (2) | 0.0213 (17) | −0.0027 (18) | 0.0054 (18) |
C4 | 0.0713 (17) | 0.0595 (16) | 0.0708 (18) | 0.0055 (13) | 0.0066 (15) | −0.0046 (14) |
C5 | 0.0500 (13) | 0.0518 (13) | 0.0579 (15) | −0.0019 (11) | 0.0125 (11) | 0.0015 (12) |
C6 | 0.0490 (13) | 0.0567 (14) | 0.0504 (13) | −0.0009 (11) | 0.0146 (11) | 0.0006 (11) |
C7 | 0.0716 (17) | 0.0738 (18) | 0.0531 (16) | 0.0097 (14) | 0.0147 (14) | −0.0050 (14) |
C8 | 0.0739 (19) | 0.098 (2) | 0.0507 (16) | −0.0005 (17) | 0.0103 (15) | 0.0084 (16) |
C9 | 0.0701 (19) | 0.081 (2) | 0.0639 (18) | 0.0116 (16) | 0.0085 (15) | 0.0116 (16) |
C10 | 0.0681 (18) | 0.0674 (18) | 0.0710 (19) | 0.0138 (14) | 0.0101 (15) | 0.0034 (14) |
C11 | 0.0621 (17) | 0.0529 (15) | 0.0728 (18) | −0.0060 (12) | 0.0234 (15) | −0.0125 (12) |
C12 | 0.104 (2) | 0.0500 (14) | 0.0812 (19) | −0.0052 (14) | 0.0472 (18) | −0.0095 (14) |
C13 | 0.155 (4) | 0.084 (2) | 0.081 (2) | −0.020 (3) | 0.056 (3) | −0.0093 (19) |
C14 | 0.119 (3) | 0.144 (3) | 0.153 (4) | 0.010 (2) | 0.089 (3) | 0.005 (3) |
C15 | 0.0705 (18) | 0.0624 (16) | 0.0520 (14) | 0.0061 (14) | 0.0193 (14) | −0.0061 (12) |
C16 | 0.101 (2) | 0.0637 (17) | 0.0669 (17) | −0.0049 (15) | 0.0361 (16) | −0.0069 (14) |
C17 | 0.147 (4) | 0.093 (3) | 0.104 (3) | −0.034 (3) | 0.044 (3) | 0.000 (2) |
C18 | 0.160 (3) | 0.080 (2) | 0.161 (4) | 0.039 (2) | 0.067 (3) | 0.030 (2) |
Ni1—O3 | 1.9669 (18) | C4—H4 | 0.944 (16) |
Ni1—N2 | 1.980 (2) | C6—C7 | 1.395 (3) |
Ni1—N1 | 1.9801 (18) | C7—C8 | 1.351 (4) |
Ni1—O1 | 1.9843 (17) | C7—H5 | 0.921 (15) |
O1—C11 | 1.260 (3) | C8—C9 | 1.378 (4) |
O2—C11 | 1.235 (3) | C8—H6 | 1.01 (3) |
O3—C15 | 1.269 (3) | C9—C10 | 1.343 (4) |
O4—C15 | 1.228 (3) | C9—H7 | 0.93 (3) |
O5—H20 | 0.961 (18) | C10—H8 | 1.00 (3) |
O5—H21 | 0.921 (18) | C11—C12 | 1.483 (4) |
O6—H6A | 0.8498 | C12—C13 | 1.327 (5) |
O6—H6B | 0.8497 | C12—C14 | 1.453 (4) |
N1—C5 | 1.335 (3) | C13—H9 | 0.930 (18) |
N1—C1 | 1.352 (3) | C13—H10 | 0.95 (4) |
N2—C6 | 1.333 (3) | C14—H13 | 0.9600 |
N2—C10 | 1.361 (3) | C14—H11 | 0.9600 |
N3—C6 | 1.371 (3) | C14—H12 | 0.9600 |
N3—C5 | 1.371 (3) | C15—C16 | 1.494 (4) |
N3—H19 | 0.8600 | C16—C17 | 1.389 (5) |
C1—C2 | 1.344 (4) | C16—C18 | 1.407 (4) |
C1—H1 | 0.90 (3) | C17—H14 | 0.911 (18) |
C2—C3 | 1.383 (4) | C17—H15 | 0.906 (19) |
C2—H2 | 0.954 (18) | C18—H17 | 0.9600 |
C3—C4 | 1.353 (4) | C18—H18 | 0.9600 |
C3—H3 | 1.00 (3) | C18—H16 | 0.9600 |
C4—C5 | 1.387 (3) | ||
O3—Ni1—N2 | 93.16 (8) | C7—C8—C9 | 119.6 (3) |
O3—Ni1—N1 | 154.32 (8) | C7—C8—H6 | 118.8 (17) |
N2—Ni1—N1 | 92.47 (8) | C9—C8—H6 | 121.5 (17) |
O3—Ni1—O1 | 92.24 (8) | C10—C9—C8 | 118.3 (3) |
N2—Ni1—O1 | 153.74 (8) | C10—C9—H7 | 118.8 (16) |
N1—Ni1—O1 | 93.70 (7) | C8—C9—H7 | 122.9 (16) |
C11—O1—Ni1 | 102.29 (16) | C9—C10—N2 | 123.9 (3) |
C15—O3—Ni1 | 105.48 (16) | C9—C10—H8 | 119.4 (15) |
H20—O5—H21 | 103 (3) | N2—C10—H8 | 116.7 (15) |
H6A—O6—H6B | 107.1 | O2—C11—O1 | 120.6 (2) |
C5—N1—C1 | 116.6 (2) | O2—C11—C12 | 120.0 (3) |
C5—N1—Ni1 | 125.95 (16) | O1—C11—C12 | 119.3 (3) |
C1—N1—Ni1 | 117.08 (18) | C13—C12—C14 | 123.5 (4) |
C6—N2—C10 | 117.4 (2) | C13—C12—C11 | 118.8 (3) |
C6—N2—Ni1 | 126.19 (16) | C14—C12—C11 | 117.7 (3) |
C10—N2—Ni1 | 116.32 (18) | C12—C13—H9 | 124 (2) |
C6—N3—C5 | 132.90 (19) | C12—C13—H10 | 112 (3) |
C6—N3—H19 | 113.5 | H9—C13—H10 | 124 (4) |
C5—N3—H19 | 113.5 | C12—C14—H13 | 109.5 |
C2—C1—N1 | 124.4 (3) | C12—C14—H11 | 109.5 |
C2—C1—H1 | 119.6 (17) | H13—C14—H11 | 109.5 |
N1—C1—H1 | 115.9 (18) | C12—C14—H12 | 109.5 |
C1—C2—C3 | 118.4 (3) | H13—C14—H12 | 109.5 |
C1—C2—H2 | 122.5 (18) | H11—C14—H12 | 109.5 |
C3—C2—H2 | 118.8 (17) | O4—C15—O3 | 121.8 (2) |
C4—C3—C2 | 118.8 (3) | O4—C15—C16 | 121.0 (3) |
C4—C3—H3 | 119 (2) | O3—C15—C16 | 117.2 (2) |
C2—C3—H3 | 122 (2) | C17—C16—C18 | 123.6 (4) |
C3—C4—C5 | 119.9 (3) | C17—C16—C15 | 118.1 (3) |
C3—C4—H4 | 123.9 (15) | C18—C16—C15 | 118.3 (3) |
C5—C4—H4 | 116.1 (15) | C16—C17—H14 | 116 (3) |
N1—C5—N3 | 120.8 (2) | C16—C17—H15 | 117 (3) |
N1—C5—C4 | 121.9 (2) | H14—C17—H15 | 126 (4) |
N3—C5—C4 | 117.3 (2) | C16—C18—H17 | 109.5 |
N2—C6—N3 | 120.8 (2) | C16—C18—H18 | 109.5 |
N2—C6—C7 | 121.1 (2) | H17—C18—H18 | 109.5 |
N3—C6—C7 | 118.1 (2) | C16—C18—H16 | 109.5 |
C8—C7—C6 | 119.8 (3) | H17—C18—H16 | 109.5 |
C8—C7—H5 | 122.3 (14) | H18—C18—H16 | 109.5 |
C6—C7—H5 | 117.9 (14) | ||
O3—Ni1—O1—C11 | 90.93 (15) | C6—N3—C5—C4 | 175.2 (2) |
N2—Ni1—O1—C11 | −10.8 (3) | C3—C4—C5—N1 | −0.4 (4) |
N1—Ni1—O1—C11 | −114.07 (15) | C3—C4—C5—N3 | −179.9 (3) |
N2—Ni1—O3—C15 | −105.33 (17) | C10—N2—C6—N3 | −179.7 (2) |
N1—Ni1—O3—C15 | −2.9 (3) | Ni1—N2—C6—N3 | −3.6 (3) |
O1—Ni1—O3—C15 | 100.38 (17) | C10—N2—C6—C7 | 0.1 (3) |
O3—Ni1—N1—C5 | −94.3 (2) | Ni1—N2—C6—C7 | 176.25 (17) |
N2—Ni1—N1—C5 | 8.28 (19) | C5—N3—C6—N2 | 9.6 (4) |
O1—Ni1—N1—C5 | 162.74 (18) | C5—N3—C6—C7 | −170.3 (2) |
O3—Ni1—N1—C1 | 78.9 (3) | N2—C6—C7—C8 | 0.0 (4) |
N2—Ni1—N1—C1 | −178.6 (2) | N3—C6—C7—C8 | 179.8 (2) |
O1—Ni1—N1—C1 | −24.1 (2) | C6—C7—C8—C9 | −0.3 (4) |
O3—Ni1—N2—C6 | 151.52 (18) | C7—C8—C9—C10 | 0.5 (4) |
N1—Ni1—N2—C6 | −3.41 (19) | C8—C9—C10—N2 | −0.4 (4) |
O1—Ni1—N2—C6 | −106.9 (2) | C6—N2—C10—C9 | 0.1 (4) |
O3—Ni1—N2—C10 | −32.28 (19) | Ni1—N2—C10—C9 | −176.4 (2) |
N1—Ni1—N2—C10 | 172.79 (18) | Ni1—O1—C11—O2 | 0.2 (3) |
O1—Ni1—N2—C10 | 69.3 (3) | Ni1—O1—C11—C12 | 178.91 (18) |
C5—N1—C1—C2 | −0.7 (4) | O2—C11—C12—C13 | 172.6 (3) |
Ni1—N1—C1—C2 | −174.4 (3) | O1—C11—C12—C13 | −6.1 (4) |
N1—C1—C2—C3 | −0.7 (5) | O2—C11—C12—C14 | −7.1 (4) |
C1—C2—C3—C4 | 1.6 (5) | O1—C11—C12—C14 | 174.2 (3) |
C2—C3—C4—C5 | −1.1 (5) | Ni1—O3—C15—O4 | −0.5 (3) |
C1—N1—C5—N3 | −179.3 (2) | Ni1—O3—C15—C16 | 179.79 (18) |
Ni1—N1—C5—N3 | −6.1 (3) | O4—C15—C16—C17 | −12.7 (4) |
C1—N1—C5—C4 | 1.2 (4) | O3—C15—C16—C17 | 167.0 (3) |
Ni1—N1—C5—C4 | 174.35 (18) | O4—C15—C16—C18 | 165.4 (3) |
C6—N3—C5—N1 | −4.3 (4) | O3—C15—C16—C18 | −14.9 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O6—H6B···O2i | 0.85 | 2.57 | 3.172 | 129 |
O6—H6B···O3i | 0.85 | 2.31 | 3.030 | 143 |
N3—H19···O5ii | 0.86 | 1.99 | 2.837 (3) | 170 |
O5—H20···O2 | 0.96 (3) | 1.75 (3) | 2.698 (3) | 169 (2) |
O5—H21···O4iii | 0.92 (3) | 1.88 (3) | 2.789 (3) | 169 (3) |
Symmetry codes: (i) −x+1/2, y+1/2, −z+3/2; (ii) −x+1, −y, −z+1; (iii) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | [Ni(C4H5O2)2(C10H9N3)]·1.5H2O |
Mr | 427.10 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 8.3686 (9), 15.7235 (16), 15.5396 (17) |
β (°) | 101.483 (2) |
V (Å3) | 2003.8 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.00 |
Crystal size (mm) | 0.29 × 0.22 × 0.18 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.740, 0.872 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9960, 3512, 2720 |
Rint | 0.077 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.036, 0.084, 1.00 |
No. of reflections | 3512 |
No. of parameters | 311 |
No. of restraints | 13 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.32, −0.24 |
Computer programs: SMART (Bruker, 1996), SAINT (Bruker, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
Ni1—O3 | 1.9669 (18) | Ni1—N1 | 1.9801 (18) |
Ni1—N2 | 1.980 (2) | Ni1—O1 | 1.9843 (17) |
O3—Ni1—N2 | 93.16 (8) | O3—Ni1—O1 | 92.24 (8) |
O3—Ni1—N1 | 154.32 (8) | N2—Ni1—O1 | 153.74 (8) |
N2—Ni1—N1 | 92.47 (8) | N1—Ni1—O1 | 93.70 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
O6—H6B···O3i | 0.85 | 2.31 | 3.030 | 143 |
N3—H19···O5ii | 0.86 | 1.99 | 2.837 (3) | 170 |
O5—H20···O2 | 0.96 (3) | 1.75 (3) | 2.698 (3) | 169 (2) |
O5—H21···O4iii | 0.92 (3) | 1.88 (3) | 2.789 (3) | 169 (3) |
Symmetry codes: (i) −x+1/2, y+1/2, −z+3/2; (ii) −x+1, −y, −z+1; (iii) x−1, y, z. |
Acknowledgements
The authors thank the Postgraduate Foundation of Daqing Normal University for financial support.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Methacrylic acid and its derivatives are biologically active compounds which are widely used as herbicides and plantgrowth substances (Matsui et al., 1997; Carabias-Martínez et al., 2006). Due to their versatile bonding modes with metal ions, they have also been used in the synthesis of mononuclear or multi-nuclear compounds (Wang et al., 1997; Wu et al., 2002). In order to develop some new topological structures, the reaction system of a nickel(II)chloride with methacrylic acid and dipyridin-2-ylamine has been explored.
Herein we report the structure of the title compound (Fig. 1). It is isostructural with the Cu analog (Liu et al., 2006) but we have located and refined an addtional half of a water solvent molecule. The NiII ion is in a distorted square-planar coordination environment, formed by two O atoms from two methacrylate ligands and two N atoms from a bis-chelataing dipyridin-2-ylamine ligand. In the crystal structure, intermolecular O—H···O and N—H···O hydrogen bonds link complex molecules and water molecules into a to form one-dimensional chains (Fig. 2).