metal-organic compounds
Diaqua{2,2′-dimethoxy-6,6′-[(1E,1′E)-propane-1,3-diylbis(azanylylidene)bis(methanylylidene)]diphenolato}nickel(II)
aDepartment of Chemistry, National Changhua University of Education, Changhua 50058, Taiwan, bDepartment of Inorganic and Radiation Chemistry, Institute of Chemistry, University of Silesia, 9th Szkolna Street, 40-006 Katowice, Poland, and cDepartment of Occupational Health and Safety, Chang Jung Christian University, Tainan City 71101, Taiwan
*Correspondence e-mail: scschem@mail.cjcu.edu.tw
In the molecule of the title compound, [Ni(C19H20N2O4)(H2O)2], the central NiII ion lies on a mirror plane and is surrounded by an N2O4 coordination set in the form of a distorted octahedron defined by the O atoms of two water molecules and by two phenolic O and two imine N atoms of the tetradentate Schiff base ligand. In the crystal, O—H⋯O hydrogen bonds between the water molecules and the phenolic and methoxy O atoms of neighbouring molecules lead to the formation of rods propagating parallel to [100].
Related literature
For related complexes with similar ligands, see: Sen et al. (2006); Thakurta et al. (2009a,b, 2010a,b).
Experimental
Crystal data
|
|
Data collection: APEX2 (Bruker, 2007); cell SAINT (Bruker, 2007); 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: publCIF (Westrip, 2010).
Supporting information
https://doi.org/10.1107/S1600536813016188/wm2747sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813016188/wm2747Isup2.hkl
The tetradentate Schiff base precursor was prepared according to the literature procedure (Sen et al., 2006). To a hot methanolic solution (20 ml) of Ni(CH3COO)2.4H2O (0.248 g, 1.0 mmol), the ligand (1.0 mmol) was added, which produced immediately an intensely brown solution. The mixture was then kept at room temperature. After slow evaporation of the brown solution, dark chocolate-brown single crystals with a rectangular form were separated out in 5 days. The crystals were filtered off and washed with water and dried in air.
Carbon-bound H-atoms were placed in calculated positions (C—H 0.93 to 0.97 Å) and were included in the
in the riding model approximation. The H atoms of the water molecules were located in a difference map and were refined with an O—H distances restraint of 0.85 (1) Å.In the title compound, [Ni(C19H20N2O4)(H2O)2], the Ni(II) ion has
m and exhibits a distorted octahedral coordination environment defined by two water molecules and the tetradentate ligand, 6,6'-(1E,1'E)-(propane-1,3-diylbis(azan-1-yl-1-ylidene)bis(methan-1-yl-1-ylidene)bis(2-methoxyphenol) (L) that coordinates via two phenolic O and two imine N atoms (Fig. 1). The bond angles around the Ni(II) ion are slightly distorted from those of a regular octahedron and range from 85.57 (7)° to 175.62 (8)°. The two Owater molecules lie at the trans position of the octahedron. The cis Ni—Ophenolic bond lengths [2.0131 (13) Å] is considerably smaller than the trans Ni—Owater bond lengths [2.113 (2) and 2.1048 (19) Å] (Table 1). In the molecule, the dihedral angle between the (C1—C7, N1) plane and its symmetry-related counterpart (C1A—C7A, N1A) is 27.58 (7)° [A) x, 1/2 - y, z].The resulting coordination geometry around the metal cation is comparable to that of complexes with similar Schiff-bases. See, for example: Thakurta et al. (2009a,b,2010a,b).
In the
of the title comound, intermolecular O—H···O hydrogen bonds between water molecules as donor groups and phenolic O and methoxy O atoms of neighbouring molecules as acceptor groups are observed (Table 2). The hydrogen bonding interactions lead to the formation of rods propagating parallel to [100] (Fig. 2).For related complexes with similar ligands, see: Sen et al. (2006); Thakurta et al. (2009a,b, 2010a,b).
Data collection: APEX2 (Bruker, 2007); cell
SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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: publCIF (Westrip, 2010).Fig. 1. The molecular structure of the title complex, showing displacement ellipsoids at the 50% probability level. [Symmetry code: (A) x, 1/2 - y, z]. | |
Fig. 2. Packing diagram of the title compound as viewed down the a axis. Intermolecular O—H···O hydrogen bonds are shown as dashed lines. |
[Ni(C19H20N2O4)(H2O)2] | F(000) = 912 |
Mr = 435.11 | Dx = 1.501 Mg m−3 |
Orthorhombic, Pnma | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2n | Cell parameters from 8168 reflections |
a = 7.4920 (2) Å | θ = 3.4–29.2° |
b = 22.1442 (6) Å | µ = 1.05 mm−1 |
c = 11.6045 (3) Å | T = 295 K |
V = 1925.24 (9) Å3 | Rectangular, brown |
Z = 4 | 0.30 × 0.25 × 0.20 mm |
Bruker SMART CCD diffractometer | 1745 independent reflections |
Radiation source: fine-focus sealed tube | 1578 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
phi and ω scans | θmax = 25.0°, θmin = 3.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2007) | h = −8→8 |
Tmin = 0.782, Tmax = 1.000 | k = −26→26 |
20064 measured reflections | l = −13→13 |
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)] = 0.025 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.073 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0386P)2 + 0.966P] where P = (Fo2 + 2Fc2)/3 |
1745 reflections | (Δ/σ)max < 0.001 |
142 parameters | Δρmax = 0.80 e Å−3 |
2 restraints | Δρmin = −0.31 e Å−3 |
[Ni(C19H20N2O4)(H2O)2] | V = 1925.24 (9) Å3 |
Mr = 435.11 | Z = 4 |
Orthorhombic, Pnma | Mo Kα radiation |
a = 7.4920 (2) Å | µ = 1.05 mm−1 |
b = 22.1442 (6) Å | T = 295 K |
c = 11.6045 (3) Å | 0.30 × 0.25 × 0.20 mm |
Bruker SMART CCD diffractometer | 1745 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2007) | 1578 reflections with I > 2σ(I) |
Tmin = 0.782, Tmax = 1.000 | Rint = 0.035 |
20064 measured reflections |
R[F2 > 2σ(F2)] = 0.025 | 2 restraints |
wR(F2) = 0.073 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.80 e Å−3 |
1745 reflections | Δρmin = −0.31 e Å−3 |
142 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 | 0.47233 (4) | 0.2500 | 0.10284 (3) | 0.02817 (13) | |
N1 | 0.4635 (2) | 0.31989 (7) | −0.01527 (14) | 0.0375 (4) | |
O1 | 0.48285 (18) | 0.31175 (5) | 0.22998 (11) | 0.0359 (3) | |
O2 | 0.4497 (2) | 0.36489 (7) | 0.42580 (13) | 0.0531 (4) | |
O3 | 0.7532 (3) | 0.2500 | 0.08662 (18) | 0.0406 (5) | |
O4 | 0.1914 (3) | 0.2500 | 0.10516 (17) | 0.0376 (4) | |
C1 | 0.4402 (2) | 0.36858 (8) | 0.22558 (17) | 0.0324 (4) | |
C2 | 0.4123 (3) | 0.40152 (8) | 0.12334 (18) | 0.0378 (4) | |
C3 | 0.3675 (3) | 0.46364 (9) | 0.1292 (2) | 0.0512 (6) | |
H3 | 0.3515 | 0.4853 | 0.0613 | 0.061* | |
C4 | 0.3474 (3) | 0.49203 (10) | 0.2318 (2) | 0.0605 (7) | |
H4 | 0.3166 | 0.5327 | 0.2339 | 0.073* | |
C5 | 0.3728 (3) | 0.46043 (9) | 0.3339 (2) | 0.0527 (6) | |
H5 | 0.3581 | 0.4799 | 0.4042 | 0.063* | |
C6 | 0.4197 (3) | 0.40052 (8) | 0.33109 (18) | 0.0396 (5) | |
C7 | 0.4323 (3) | 0.37529 (9) | 0.01098 (18) | 0.0423 (5) | |
H7 | 0.4212 | 0.4018 | −0.0508 | 0.051* | |
C8 | 0.4391 (4) | 0.39102 (12) | 0.5356 (2) | 0.0696 (8) | |
H8A | 0.5251 | 0.4230 | 0.5417 | 0.104* | |
H8B | 0.4636 | 0.3609 | 0.5930 | 0.104* | |
H8C | 0.3214 | 0.4070 | 0.5474 | 0.104* | |
C9 | 0.4892 (4) | 0.30703 (12) | −0.1376 (2) | 0.0594 (6) | |
H9A | 0.6162 | 0.3042 | −0.1531 | 0.071* | |
H9B | 0.4428 | 0.3406 | −0.1822 | 0.071* | |
C10 | 0.4007 (5) | 0.2500 | −0.1775 (3) | 0.0624 (9) | |
H10A | 0.2782 | 0.2500 | −0.1504 | 0.075* | |
H10B | 0.3976 | 0.2500 | −0.2610 | 0.075* | |
H4O | 0.150 (3) | 0.2810 (7) | 0.1357 (19) | 0.059 (7)* | |
H3O | 0.802 (3) | 0.2808 (8) | 0.113 (2) | 0.067 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.0280 (2) | 0.0281 (2) | 0.0284 (2) | 0.000 | −0.00017 (12) | 0.000 |
N1 | 0.0365 (9) | 0.0418 (9) | 0.0342 (9) | 0.0008 (7) | 0.0009 (7) | 0.0074 (7) |
O1 | 0.0469 (8) | 0.0247 (6) | 0.0360 (7) | 0.0037 (5) | −0.0038 (6) | −0.0011 (5) |
O2 | 0.0838 (12) | 0.0355 (8) | 0.0401 (8) | −0.0063 (7) | 0.0054 (8) | −0.0076 (6) |
O3 | 0.0287 (10) | 0.0336 (11) | 0.0596 (13) | 0.000 | −0.0046 (9) | 0.000 |
O4 | 0.0288 (10) | 0.0396 (12) | 0.0443 (11) | 0.000 | 0.0044 (8) | 0.000 |
C1 | 0.0260 (9) | 0.0251 (8) | 0.0461 (11) | −0.0024 (7) | 0.0001 (8) | −0.0005 (7) |
C2 | 0.0306 (10) | 0.0315 (10) | 0.0514 (12) | 0.0004 (8) | −0.0014 (8) | 0.0058 (8) |
C3 | 0.0481 (13) | 0.0344 (11) | 0.0711 (16) | 0.0043 (9) | −0.0079 (11) | 0.0100 (10) |
C4 | 0.0610 (15) | 0.0280 (10) | 0.093 (2) | 0.0089 (10) | −0.0026 (13) | −0.0029 (12) |
C5 | 0.0551 (13) | 0.0333 (11) | 0.0698 (16) | −0.0011 (9) | 0.0075 (11) | −0.0142 (10) |
C6 | 0.0383 (10) | 0.0310 (10) | 0.0494 (12) | −0.0057 (8) | 0.0040 (9) | −0.0036 (8) |
C7 | 0.0406 (11) | 0.0406 (11) | 0.0457 (12) | 0.0008 (9) | −0.0037 (9) | 0.0154 (9) |
C8 | 0.099 (2) | 0.0630 (16) | 0.0469 (14) | −0.0099 (15) | 0.0072 (13) | −0.0182 (12) |
C9 | 0.0818 (18) | 0.0607 (16) | 0.0357 (12) | 0.0025 (13) | 0.0073 (11) | 0.0096 (11) |
C10 | 0.076 (2) | 0.077 (2) | 0.0342 (17) | 0.000 | −0.0113 (16) | 0.000 |
Ni1—O1i | 2.0131 (13) | C3—C4 | 1.355 (3) |
Ni1—O1 | 2.0131 (13) | C3—H3 | 0.9300 |
Ni1—N1 | 2.0684 (16) | C4—C5 | 1.389 (3) |
Ni1—N1i | 2.0684 (16) | C4—H4 | 0.9300 |
Ni1—O4 | 2.1048 (19) | C5—C6 | 1.373 (3) |
Ni1—O3 | 2.113 (2) | C5—H5 | 0.9300 |
N1—C7 | 1.286 (3) | C7—H7 | 0.9300 |
N1—C9 | 1.461 (3) | C8—H8A | 0.9600 |
O1—C1 | 1.299 (2) | C8—H8B | 0.9600 |
O2—C6 | 1.372 (3) | C8—H8C | 0.9600 |
O2—C8 | 1.402 (3) | C9—C10 | 1.500 (3) |
O3—H3O | 0.830 (10) | C9—H9A | 0.9700 |
O4—H4O | 0.833 (9) | C9—H9B | 0.9700 |
C1—C2 | 1.408 (3) | C10—C9i | 1.500 (3) |
C1—C6 | 1.422 (3) | C10—H10A | 0.9700 |
C2—C3 | 1.418 (3) | C10—H10B | 0.9700 |
C2—C7 | 1.435 (3) | ||
O1i—Ni1—O1 | 85.57 (7) | C3—C4—C5 | 120.0 (2) |
O1i—Ni1—N1 | 174.34 (6) | C3—C4—H4 | 120.0 |
O1—Ni1—N1 | 88.78 (6) | C5—C4—H4 | 120.0 |
O1i—Ni1—N1i | 88.78 (6) | C6—C5—C4 | 120.1 (2) |
O1—Ni1—N1i | 174.34 (6) | C6—C5—H5 | 119.9 |
N1—Ni1—N1i | 96.88 (9) | C4—C5—H5 | 119.9 |
O1i—Ni1—O4 | 91.71 (6) | O2—C6—C5 | 125.4 (2) |
O1—Ni1—O4 | 91.71 (6) | O2—C6—C1 | 112.71 (16) |
N1—Ni1—O4 | 88.65 (6) | C5—C6—C1 | 121.9 (2) |
N1i—Ni1—O4 | 88.65 (6) | N1—C7—C2 | 128.35 (18) |
O1i—Ni1—O3 | 91.51 (6) | N1—C7—H7 | 115.8 |
O1—Ni1—O3 | 91.51 (6) | C2—C7—H7 | 115.8 |
N1—Ni1—O3 | 88.44 (6) | O2—C8—H8A | 109.5 |
N1i—Ni1—O3 | 88.44 (6) | O2—C8—H8B | 109.5 |
O4—Ni1—O3 | 175.62 (8) | H8A—C8—H8B | 109.5 |
C7—N1—C9 | 116.12 (18) | O2—C8—H8C | 109.5 |
C7—N1—Ni1 | 124.25 (14) | H8A—C8—H8C | 109.5 |
C9—N1—Ni1 | 119.60 (15) | H8B—C8—H8C | 109.5 |
C1—O1—Ni1 | 128.27 (12) | N1—C9—C10 | 113.9 (2) |
C6—O2—C8 | 118.81 (18) | N1—C9—H9A | 108.8 |
Ni1—O3—H3O | 113.9 (19) | C10—C9—H9A | 108.8 |
Ni1—O4—H4O | 112.4 (17) | N1—C9—H9B | 108.8 |
O1—C1—C2 | 124.84 (17) | C10—C9—H9B | 108.8 |
O1—C1—C6 | 118.32 (17) | H9A—C9—H9B | 107.7 |
C2—C1—C6 | 116.85 (16) | C9i—C10—C9 | 114.7 (3) |
C1—C2—C3 | 119.82 (19) | C9i—C10—H10A | 108.6 |
C1—C2—C7 | 122.70 (17) | C9—C10—H10A | 108.6 |
C3—C2—C7 | 117.45 (19) | C9i—C10—H10B | 108.6 |
C4—C3—C2 | 121.2 (2) | C9—C10—H10B | 108.6 |
C4—C3—H3 | 119.4 | H10A—C10—H10B | 107.6 |
C2—C3—H3 | 119.4 |
Symmetry code: (i) x, −y+1/2, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4O···O2ii | 0.83 (1) | 2.49 (2) | 3.1433 (19) | 136 (2) |
O4—H4O···O1ii | 0.83 (1) | 2.11 (2) | 2.823 (2) | 143 (2) |
O3—H3O···O1iii | 0.83 (1) | 2.37 (2) | 3.059 (2) | 140 (2) |
O3—H3O···O2iii | 0.83 (1) | 2.21 (2) | 2.9432 (18) | 147 (2) |
Symmetry codes: (ii) x−1/2, y, −z+1/2; (iii) x+1/2, y, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [Ni(C19H20N2O4)(H2O)2] |
Mr | 435.11 |
Crystal system, space group | Orthorhombic, Pnma |
Temperature (K) | 295 |
a, b, c (Å) | 7.4920 (2), 22.1442 (6), 11.6045 (3) |
V (Å3) | 1925.24 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.05 |
Crystal size (mm) | 0.30 × 0.25 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2007) |
Tmin, Tmax | 0.782, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 20064, 1745, 1578 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.025, 0.073, 1.06 |
No. of reflections | 1745 |
No. of parameters | 142 |
No. of restraints | 2 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.80, −0.31 |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), publCIF (Westrip, 2010).
Ni1—O1i | 2.0131 (13) | Ni1—N1i | 2.0684 (16) |
Ni1—O1 | 2.0131 (13) | Ni1—O4 | 2.1048 (19) |
Ni1—N1 | 2.0684 (16) | Ni1—O3 | 2.113 (2) |
Symmetry code: (i) x, −y+1/2, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4O···O2ii | 0.833 (9) | 2.491 (18) | 3.1433 (19) | 136 (2) |
O4—H4O···O1ii | 0.833 (9) | 2.111 (17) | 2.823 (2) | 143 (2) |
O3—H3O···O1iii | 0.830 (10) | 2.374 (18) | 3.059 (2) | 140 (2) |
O3—H3O···O2iii | 0.830 (10) | 2.214 (16) | 2.9432 (18) | 147 (2) |
Symmetry codes: (ii) x−1/2, y, −z+1/2; (iii) x+1/2, y, −z+1/2. |
Acknowledgements
We are grateful to the National Science Council of Taiwan for financial support.
References
Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc. Madison, Wisconsin, USA. Google Scholar
Sen, S., Mitra, S., Luneau, D., El Fallah, M. S. & Ribas, J. (2006). Polyhedron, 25, 2737–2744. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Thakurta, S., Butcher, R. J., Gómez-García, C. J., Garribba, E. & Mitra, S. (2010b). Inorg. Chim. Acta, 363, 3981–3986. Web of Science CSD CrossRef CAS Google Scholar
Thakurta, S., Butcher, R. J., Pilet, G. & Mitra, S. (2009b). J. Mol. Struct. 929, 112–119. Web of Science CSD CrossRef CAS Google Scholar
Thakurta, S., Chakraborty, J., Rosair, G. M., Butcher, R. J. & Mitra, S. (2009a). Inorg. Chim. Acta, 362, 2828–2836. Web of Science CSD CrossRef CAS Google Scholar
Thakurta, S., Rizzoli, C., Butcher, R. J., Gómez-García, C. J., Garribba, E. & Mitra, S. (2010a). Inorg. Chim. Acta, 363, 2395–1403. Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
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.
In the title compound, [Ni(C19H20N2O4)(H2O)2], the Ni(II) ion has site symmetry m and exhibits a distorted octahedral coordination environment defined by two water molecules and the tetradentate ligand, 6,6'-(1E,1'E)-(propane-1,3-diylbis(azan-1-yl-1-ylidene)bis(methan-1-yl-1-ylidene)bis(2-methoxyphenol) (L) that coordinates via two phenolic O and two imine N atoms (Fig. 1). The bond angles around the Ni(II) ion are slightly distorted from those of a regular octahedron and range from 85.57 (7)° to 175.62 (8)°. The two Owater molecules lie at the trans position of the octahedron. The cis Ni—Ophenolic bond lengths [2.0131 (13) Å] is considerably smaller than the trans Ni—Owater bond lengths [2.113 (2) and 2.1048 (19) Å] (Table 1). In the molecule, the dihedral angle between the (C1—C7, N1) plane and its symmetry-related counterpart (C1A—C7A, N1A) is 27.58 (7)° [A) x, 1/2 - y, z].
The resulting coordination geometry around the metal cation is comparable to that of complexes with similar Schiff-bases. See, for example: Thakurta et al. (2009a,b,2010a,b).
In the crystal structure of the title comound, intermolecular O—H···O hydrogen bonds between water molecules as donor groups and phenolic O and methoxy O atoms of neighbouring molecules as acceptor groups are observed (Table 2). The hydrogen bonding interactions lead to the formation of rods propagating parallel to [100] (Fig. 2).