metal-organic compounds
Bis{4-[(Z)-(4-fluorobenzylamino)(phenyl)methylene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-onato-κ2N4,O}nickel(II)
aCollege of Chemistry and Life Sciences, Tianjin Normal University, Tianjin 300074, People's Republic of China
*Correspondence e-mail: zxin_tj@126.com
The molecule of the title compound, [Ni(C24H19FN3O)2], has twofold rotation symmetry. The NiII ion is in a square-planar coordination geometry which is distorted towards tetrahedral and is coordinated by two N atoms of imine and two O atoms of pyrazolone from two Schiff base 4-[(Z)-(4-fluorobenzylamino)phenylmethylene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-onate ligands.
Related literature
For related literature, see: Sesser et al. (1993); Smith et al. (1989); Padhy et al. (1985); Yu et al. (1993); Wu et al. (1993); Zhao (2007); Peng et al. (2006); Xu et al. (2006); Bao et al. (2005); Ma et al. (2006); Wang (2006); Li & Wang (2007).
Experimental
Crystal data
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Data collection: SMART (Bruker, 1998); cell SAINT (Bruker, 1998); 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/S1600536808009197/lx2051sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808009197/lx2051Isup2.hkl
(4Z)-4-[(4-Fluorobenzylamino)(phenyl)-methylene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one (1.0 mmol) and Ni(Ac)2 (1.0 mmol) were dissolved in MeOH (10 ml). The mixture was stirred at room temperature for about 1 h, then heated to reflux for 3 h. After allowing the solution to stand in air for 7 d, green lock-shaped crystals were formed with a yield of 40%.
Although all H atoms were visible in difference maps, they were placed in geometrically calculated positions, with C—H distances in the range 0.93–0.97 Å, and included in the final
in the riding model approximation,with Uiso(H) = 1.2Ueq(C) for aromatic and methylene H atoms,with Uiso(H) = 1.5Ueq(C) for methylic H atomsData collection: SMART (Bruker, 1998); cell
SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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 (I), with anisotropic displacement ellipsoids drawn at the 30% probability level [Symmetry code: (i) -x + 1,y,-z + 1/2.] |
[Ni(C24H19FN3O)2] | F(000) = 1720 |
Mr = 827.55 | Dx = 1.352 Mg m−3 |
Orthorhombic, Pbcn | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2n 2ab | Cell parameters from 3309 reflections |
a = 25.475 (2) Å | θ = 2.5–22.0° |
b = 10.1620 (8) Å | µ = 0.54 mm−1 |
c = 15.700 (1) Å | T = 293 K |
V = 4064.4 (5) Å3 | BLOCK, red |
Z = 4 | 0.24 × 0.22 × 0.18 mm |
Bruker SMART CCD diffractometer | 4867 independent reflections |
Radiation source: fine-focus sealed tube | 2916 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
Detector resolution: 10.0 pixels mm-1 | θmax = 27.9°, θmin = 2.2° |
ϕ and ω scans | h = −21→33 |
Absorption correction: multi-scan (SADABS; Bruker, 1998) | k = −13→12 |
Tmin = 0.866, Tmax = 0.910 | l = −20→18 |
26008 measured reflections |
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) = 0.076 | H-atom parameters constrained |
S = 1.42 | w = 1/[σ2(Fo2)] where P = (Fo2 + 2Fc2)/3 |
4867 reflections | (Δ/σ)max = 0.001 |
268 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−3 |
[Ni(C24H19FN3O)2] | V = 4064.4 (5) Å3 |
Mr = 827.55 | Z = 4 |
Orthorhombic, Pbcn | Mo Kα radiation |
a = 25.475 (2) Å | µ = 0.54 mm−1 |
b = 10.1620 (8) Å | T = 293 K |
c = 15.700 (1) Å | 0.24 × 0.22 × 0.18 mm |
Bruker SMART CCD diffractometer | 4867 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1998) | 2916 reflections with I > 2σ(I) |
Tmin = 0.866, Tmax = 0.910 | Rint = 0.043 |
26008 measured reflections |
R[F2 > 2σ(F2)] = 0.036 | 0 restraints |
wR(F2) = 0.076 | H-atom parameters constrained |
S = 1.42 | Δρmax = 0.20 e Å−3 |
4867 reflections | Δρmin = −0.25 e Å−3 |
268 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 | ||
Ni | 0.5000 | 0.74902 (3) | 0.2500 | 0.03705 (9) | |
F | 0.60501 (7) | 1.27896 (15) | 0.15762 (10) | 0.1420 (6) | |
O | 0.45522 (4) | 0.67156 (10) | 0.33499 (7) | 0.0455 (3) | |
N1 | 0.37188 (5) | 0.64453 (14) | 0.39135 (9) | 0.0521 (4) | |
N2 | 0.31974 (6) | 0.66922 (18) | 0.36965 (10) | 0.0710 (5) | |
N3 | 0.44445 (5) | 0.80468 (13) | 0.17239 (8) | 0.0445 (3) | |
C1 | 0.42626 (7) | 0.53082 (17) | 0.49505 (12) | 0.0615 (5) | |
H1 | 0.4466 | 0.4956 | 0.4514 | 0.074* | |
C2 | 0.43833 (8) | 0.50343 (19) | 0.57895 (14) | 0.0728 (6) | |
H2 | 0.4672 | 0.4508 | 0.5915 | 0.087* | |
C3 | 0.40835 (9) | 0.5529 (2) | 0.64395 (13) | 0.0712 (6) | |
H3 | 0.4169 | 0.5348 | 0.7003 | 0.085* | |
C4 | 0.36580 (8) | 0.6288 (2) | 0.62491 (12) | 0.0736 (6) | |
H4 | 0.3448 | 0.6611 | 0.6686 | 0.088* | |
C5 | 0.35365 (7) | 0.65816 (18) | 0.54168 (11) | 0.0612 (5) | |
H5 | 0.3247 | 0.7106 | 0.5296 | 0.073* | |
C6 | 0.38418 (6) | 0.61033 (16) | 0.47621 (11) | 0.0473 (4) | |
C7 | 0.32123 (7) | 0.7208 (2) | 0.29336 (13) | 0.0677 (6) | |
C8 | 0.37393 (6) | 0.73431 (16) | 0.26211 (10) | 0.0466 (4) | |
C9 | 0.40520 (6) | 0.68240 (16) | 0.32787 (10) | 0.0428 (4) | |
C10 | 0.26929 (8) | 0.7559 (2) | 0.25261 (14) | 0.1213 (12) | |
H10A | 0.2666 | 0.7134 | 0.1982 | 0.182* | |
H10B | 0.2672 | 0.8496 | 0.2451 | 0.182* | |
H10C | 0.2411 | 0.7272 | 0.2886 | 0.182* | |
C11 | 0.39386 (6) | 0.79288 (16) | 0.18624 (10) | 0.0446 (4) | |
C12 | 0.35452 (6) | 0.84084 (18) | 0.12212 (11) | 0.0498 (4) | |
C13 | 0.33603 (7) | 0.75812 (19) | 0.05954 (11) | 0.0587 (5) | |
H13 | 0.3490 | 0.6728 | 0.0555 | 0.070* | |
C14 | 0.29816 (7) | 0.8014 (2) | 0.00249 (13) | 0.0735 (6) | |
H14 | 0.2860 | 0.7452 | −0.0399 | 0.088* | |
C15 | 0.27871 (8) | 0.9262 (3) | 0.00842 (16) | 0.0874 (8) | |
H15 | 0.2533 | 0.9549 | −0.0298 | 0.105* | |
C16 | 0.29663 (8) | 1.0086 (2) | 0.07052 (18) | 0.0909 (8) | |
H16 | 0.2833 | 1.0936 | 0.0744 | 0.109* | |
C17 | 0.33442 (7) | 0.9671 (2) | 0.12765 (14) | 0.0735 (6) | |
H17 | 0.3464 | 1.0240 | 0.1698 | 0.088* | |
C18 | 0.46406 (6) | 0.86510 (17) | 0.09264 (10) | 0.0527 (5) | |
H18A | 0.4346 | 0.8985 | 0.0601 | 0.063* | |
H18B | 0.4814 | 0.7984 | 0.0586 | 0.063* | |
C19 | 0.50202 (7) | 0.97610 (18) | 0.11001 (10) | 0.0507 (4) | |
C20 | 0.48434 (9) | 1.0994 (2) | 0.13394 (13) | 0.0776 (6) | |
H20 | 0.4485 | 1.1140 | 0.1399 | 0.093* | |
C21 | 0.51909 (13) | 1.2011 (3) | 0.14913 (16) | 0.0981 (8) | |
H21 | 0.5070 | 1.2840 | 0.1647 | 0.118* | |
C22 | 0.57081 (12) | 1.1778 (3) | 0.14100 (14) | 0.0883 (8) | |
C23 | 0.59040 (9) | 1.0606 (3) | 0.11648 (14) | 0.0788 (7) | |
H23 | 0.6264 | 1.0477 | 0.1113 | 0.095* | |
C24 | 0.55516 (7) | 0.95964 (19) | 0.09921 (12) | 0.0612 (5) | |
H24 | 0.5678 | 0.8791 | 0.0799 | 0.073* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni | 0.02468 (14) | 0.06300 (18) | 0.02347 (13) | 0.000 | 0.00016 (12) | 0.000 |
F | 0.1785 (15) | 0.1505 (13) | 0.0970 (12) | −0.1026 (12) | −0.0011 (10) | −0.0095 (10) |
O | 0.0322 (6) | 0.0664 (7) | 0.0379 (7) | 0.0036 (6) | 0.0040 (5) | 0.0071 (6) |
N1 | 0.0325 (8) | 0.0818 (10) | 0.0421 (9) | −0.0017 (7) | 0.0053 (6) | 0.0073 (8) |
N2 | 0.0316 (9) | 0.1299 (15) | 0.0514 (11) | −0.0065 (9) | 0.0032 (7) | 0.0108 (10) |
N3 | 0.0349 (8) | 0.0695 (9) | 0.0291 (7) | −0.0051 (7) | −0.0005 (6) | 0.0011 (7) |
C1 | 0.0614 (13) | 0.0680 (13) | 0.0551 (13) | 0.0088 (10) | 0.0174 (9) | 0.0123 (11) |
C2 | 0.0678 (14) | 0.0820 (15) | 0.0686 (15) | 0.0128 (11) | 0.0094 (12) | 0.0304 (12) |
C3 | 0.0771 (16) | 0.0885 (15) | 0.0480 (13) | −0.0108 (12) | 0.0019 (11) | 0.0194 (11) |
C4 | 0.0771 (16) | 0.0996 (16) | 0.0442 (13) | 0.0030 (13) | 0.0142 (10) | −0.0034 (12) |
C5 | 0.0516 (12) | 0.0838 (14) | 0.0482 (12) | 0.0107 (10) | 0.0091 (9) | 0.0030 (10) |
C6 | 0.0410 (10) | 0.0609 (11) | 0.0400 (11) | −0.0061 (9) | 0.0066 (8) | 0.0055 (8) |
C7 | 0.0327 (10) | 0.1215 (18) | 0.0488 (12) | −0.0031 (10) | −0.0004 (9) | 0.0073 (12) |
C8 | 0.0312 (8) | 0.0730 (12) | 0.0357 (11) | −0.0037 (8) | −0.0012 (7) | 0.0015 (9) |
C9 | 0.0341 (9) | 0.0583 (10) | 0.0359 (10) | −0.0038 (8) | 0.0052 (8) | −0.0020 (8) |
C10 | 0.0306 (11) | 0.260 (4) | 0.0731 (16) | −0.0052 (15) | −0.0036 (10) | 0.0410 (19) |
C11 | 0.0332 (9) | 0.0644 (11) | 0.0360 (10) | 0.0005 (8) | −0.0043 (7) | −0.0042 (8) |
C12 | 0.0321 (10) | 0.0721 (13) | 0.0452 (11) | −0.0058 (9) | −0.0051 (8) | 0.0063 (10) |
C13 | 0.0461 (11) | 0.0822 (13) | 0.0479 (11) | −0.0086 (10) | −0.0115 (8) | 0.0055 (11) |
C14 | 0.0585 (14) | 0.1094 (17) | 0.0527 (13) | −0.0275 (12) | −0.0213 (10) | 0.0174 (12) |
C15 | 0.0522 (14) | 0.113 (2) | 0.097 (2) | −0.0190 (14) | −0.0315 (12) | 0.0466 (16) |
C16 | 0.0561 (14) | 0.0820 (16) | 0.134 (2) | 0.0067 (11) | −0.0280 (14) | 0.0224 (16) |
C17 | 0.0502 (13) | 0.0788 (14) | 0.0915 (17) | 0.0026 (11) | −0.0198 (11) | −0.0045 (12) |
C18 | 0.0408 (10) | 0.0854 (13) | 0.0319 (10) | −0.0046 (9) | −0.0045 (8) | 0.0085 (9) |
C19 | 0.0462 (11) | 0.0744 (12) | 0.0316 (9) | −0.0046 (10) | −0.0041 (8) | 0.0125 (8) |
C20 | 0.0710 (15) | 0.0945 (17) | 0.0675 (16) | −0.0001 (13) | 0.0161 (11) | −0.0024 (13) |
C21 | 0.130 (2) | 0.0836 (16) | 0.0808 (19) | −0.0205 (17) | 0.0294 (17) | −0.0168 (14) |
C22 | 0.108 (2) | 0.104 (2) | 0.0527 (14) | −0.0481 (19) | −0.0053 (14) | 0.0039 (14) |
C23 | 0.0555 (14) | 0.1039 (18) | 0.0770 (17) | −0.0236 (13) | −0.0132 (11) | 0.0407 (15) |
C24 | 0.0466 (12) | 0.0723 (13) | 0.0646 (13) | −0.0031 (10) | −0.0003 (9) | 0.0268 (11) |
Ni—Oi | 1.924 (1) | C10—H10B | 0.9600 |
Ni—O | 1.924 (1) | C10—H10C | 0.9600 |
Ni—N3i | 1.951 (1) | C11—C12 | 1.502 (2) |
Ni—N3 | 1.951 (1) | C12—C13 | 1.376 (2) |
F—C22 | 1.373 (2) | C12—C17 | 1.384 (2) |
O—C9 | 1.284 (2) | C13—C14 | 1.388 (2) |
N1—C9 | 1.365 (2) | C13—H13 | 0.9300 |
N1—N2 | 1.394 (2) | C14—C15 | 1.365 (3) |
N1—C6 | 1.412 (2) | C14—H14 | 0.9300 |
N2—C7 | 1.308 (2) | C15—C16 | 1.364 (3) |
N3—C11 | 1.313 (2) | C15—H15 | 0.9300 |
N3—C18 | 1.481 (2) | C16—C17 | 1.382 (3) |
C1—C6 | 1.375 (2) | C16—H16 | 0.9300 |
C1—C2 | 1.381 (2) | C17—H17 | 0.9300 |
C1—H1 | 0.9300 | C18—C19 | 1.511 (2) |
C2—C3 | 1.370 (3) | C18—H18A | 0.9700 |
C2—H2 | 0.9300 | C18—H18B | 0.9700 |
C3—C4 | 1.364 (3) | C19—C24 | 1.374 (2) |
C3—H3 | 0.9300 | C19—C20 | 1.383 (3) |
C4—C5 | 1.376 (2) | C20—C21 | 1.381 (3) |
C4—H4 | 0.9300 | C20—H20 | 0.9300 |
C5—C6 | 1.378 (2) | C21—C22 | 1.345 (3) |
C5—H5 | 0.9300 | C21—H21 | 0.9300 |
C7—C8 | 1.436 (2) | C22—C23 | 1.347 (3) |
C7—C10 | 1.513 (3) | C23—C24 | 1.390 (3) |
C8—C9 | 1.407 (2) | C23—H23 | 0.9300 |
C8—C11 | 1.425 (2) | C24—H24 | 0.9300 |
C10—H10A | 0.9600 | ||
Oi—Ni—O | 131.70 (6) | H10B—C10—H10C | 109.5 |
Oi—Ni—N3i | 96.99 (5) | N3—C11—C8 | 121.8 (1) |
O—Ni—N3i | 96.63 (5) | N3—C11—C12 | 121.0 (1) |
Oi—Ni—N3 | 96.63 (5) | C8—C11—C12 | 117.27 (14) |
O—Ni—N3 | 96.99 (5) | C13—C12—C17 | 119.0 (2) |
N3i—Ni—N3 | 146.30 (8) | C13—C12—C11 | 120.6 (2) |
C9—O—Ni | 119.5 (1) | C17—C12—C11 | 120.4 (2) |
C9—N1—N2 | 111.3 (1) | C12—C13—C14 | 120.4 (2) |
C9—N1—C6 | 128.4 (1) | C12—C13—H13 | 119.8 |
N2—N1—C6 | 119.1 (1) | C14—C13—H13 | 119.8 |
C7—N2—N1 | 105.6 (1) | C15—C14—C13 | 120.2 (2) |
C11—N3—C18 | 120.6 (1) | C15—C14—H14 | 119.9 |
C11—N3—Ni | 125.6 (1) | C13—C14—H14 | 119.9 |
C18—N3—Ni | 113.79 (9) | C14—C15—C16 | 119.9 (2) |
C6—C1—C2 | 119.8 (2) | C14—C15—H15 | 120.1 |
C6—C1—H1 | 120.1 | C16—C15—H15 | 120.1 |
C2—C1—H1 | 120.1 | C15—C16—C17 | 120.6 (2) |
C3—C2—C1 | 120.8 (2) | C15—C16—H16 | 119.7 |
C3—C2—H2 | 119.6 | C17—C16—H16 | 119.7 |
C1—C2—H2 | 119.6 | C12—C17—C16 | 120.0 (2) |
C4—C3—C2 | 119.2 (2) | C12—C17—H17 | 120.0 |
C4—C3—H3 | 120.4 | C16—C17—H17 | 120.0 |
C2—C3—H3 | 120.4 | N3—C18—C19 | 111.9 (1) |
C3—C4—C5 | 120.6 (2) | N3—C18—H18A | 109.2 |
C3—C4—H4 | 119.7 | C19—C18—H18A | 109.2 |
C5—C4—H4 | 119.7 | N3—C18—H18B | 109.2 |
C6—C5—C4 | 120.3 (2) | C19—C18—H18B | 109.2 |
C6—C5—H5 | 119.8 | H18A—C18—H18B | 107.9 |
C4—C5—H5 | 119.8 | C24—C19—C20 | 117.7 (2) |
C1—C6—C5 | 119.2 (2) | C24—C19—C18 | 121.2 (2) |
C1—C6—N1 | 121.4 (2) | C20—C19—C18 | 121.1 (2) |
C5—C6—N1 | 119.5 (2) | C21—C20—C19 | 121.0 (2) |
N2—C7—C8 | 112.2 (2) | C21—C20—H20 | 119.5 |
N2—C7—C10 | 117.2 (2) | C19—C20—H20 | 119.5 |
C8—C7—C10 | 130.6 (2) | C22—C21—C20 | 118.7 (2) |
C9—C8—C11 | 124.6 (2) | C22—C21—H21 | 120.7 |
C9—C8—C7 | 104.1 (2) | C20—C21—H21 | 120.7 |
C11—C8—C7 | 131.2 (2) | C21—C22—C23 | 123.1 (2) |
O—C9—N1 | 122.0 (2) | C21—C22—F | 118.2 (3) |
O—C9—C8 | 131.2 (2) | C23—C22—F | 118.8 (3) |
N1—C9—C8 | 106.8 (1) | C22—C23—C24 | 118.0 (2) |
C7—C10—H10A | 109.5 | C22—C23—H23 | 121.0 |
C7—C10—H10B | 109.5 | C24—C23—H23 | 121.0 |
H10A—C10—H10B | 109.5 | C19—C24—C23 | 121.5 (2) |
C7—C10—H10C | 109.5 | C19—C24—H24 | 119.3 |
H10A—C10—H10C | 109.5 | C23—C24—H24 | 119.3 |
Oi—Ni—O—C9 | −111.23 (12) | C11—C8—C9—N1 | 175.72 (15) |
N3i—Ni—O—C9 | 143.24 (12) | C7—C8—C9—N1 | −0.71 (18) |
N3—Ni—O—C9 | −5.86 (12) | C18—N3—C11—C8 | 179.54 (14) |
C9—N1—N2—C7 | 0.5 (2) | Ni—N3—C11—C8 | −0.8 (2) |
C6—N1—N2—C7 | 168.80 (16) | C18—N3—C11—C12 | −0.4 (2) |
Oi—Ni—N3—C11 | 137.19 (14) | Ni—N3—C11—C12 | 179.28 (12) |
O—Ni—N3—C11 | 3.64 (14) | C9—C8—C11—N3 | −1.0 (3) |
N3i—Ni—N3—C11 | −109.53 (14) | C7—C8—C11—N3 | 174.36 (17) |
Oi—Ni—N3—C18 | −43.14 (11) | C9—C8—C11—C12 | 178.89 (16) |
O—Ni—N3—C18 | −176.69 (11) | C7—C8—C11—C12 | −5.7 (3) |
N3i—Ni—N3—C18 | 70.14 (10) | N3—C11—C12—C13 | 90.9 (2) |
C6—C1—C2—C3 | 1.0 (3) | C8—C11—C12—C13 | −89.0 (2) |
C1—C2—C3—C4 | 0.7 (3) | N3—C11—C12—C17 | −92.2 (2) |
C2—C3—C4—C5 | −1.4 (3) | C8—C11—C12—C17 | 87.9 (2) |
C3—C4—C5—C6 | 0.4 (3) | C17—C12—C13—C14 | 0.6 (3) |
C2—C1—C6—C5 | −2.0 (3) | C11—C12—C13—C14 | 177.48 (16) |
C2—C1—C6—N1 | 177.55 (16) | C12—C13—C14—C15 | −0.4 (3) |
C4—C5—C6—C1 | 1.3 (3) | C13—C14—C15—C16 | 0.1 (3) |
C4—C5—C6—N1 | −178.28 (17) | C14—C15—C16—C17 | 0.1 (4) |
C9—N1—C6—C1 | −43.5 (3) | C13—C12—C17—C16 | −0.4 (3) |
N2—N1—C6—C1 | 150.35 (16) | C11—C12—C17—C16 | −177.32 (19) |
C9—N1—C6—C5 | 136.03 (18) | C15—C16—C17—C12 | 0.1 (4) |
N2—N1—C6—C5 | −30.1 (2) | C11—N3—C18—C19 | 126.69 (16) |
N1—N2—C7—C8 | −0.9 (2) | Ni—N3—C18—C19 | −53.00 (16) |
N1—N2—C7—C10 | 179.03 (17) | N3—C18—C19—C24 | 104.07 (18) |
N2—C7—C8—C9 | 1.1 (2) | N3—C18—C19—C20 | −78.6 (2) |
C10—C7—C8—C9 | −178.9 (2) | C24—C19—C20—C21 | −2.1 (3) |
N2—C7—C8—C11 | −175.04 (18) | C18—C19—C20—C21 | −179.47 (19) |
C10—C7—C8—C11 | 5.0 (4) | C19—C20—C21—C22 | −0.6 (4) |
Ni—O—C9—N1 | −171.42 (12) | C20—C21—C22—C23 | 1.8 (4) |
Ni—O—C9—C8 | 6.3 (2) | C20—C21—C22—F | −178.94 (19) |
N2—N1—C9—O | 178.37 (15) | C21—C22—C23—C24 | −0.2 (4) |
C6—N1—C9—O | 11.4 (3) | F—C22—C23—C24 | −179.45 (17) |
N2—N1—C9—C8 | 0.20 (19) | C20—C19—C24—C23 | 3.7 (3) |
C6—N1—C9—C8 | −166.79 (16) | C18—C19—C24—C23 | −178.87 (16) |
C11—C8—C9—O | −2.2 (3) | C22—C23—C24—C19 | −2.7 (3) |
C7—C8—C9—O | −178.65 (18) |
Symmetry code: (i) −x+1, y, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [Ni(C24H19FN3O)2] |
Mr | 827.55 |
Crystal system, space group | Orthorhombic, Pbcn |
Temperature (K) | 293 |
a, b, c (Å) | 25.475 (2), 10.1620 (8), 15.700 (1) |
V (Å3) | 4064.4 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.54 |
Crystal size (mm) | 0.24 × 0.22 × 0.18 |
Data collection | |
Diffractometer | Bruker SMART CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 1998) |
Tmin, Tmax | 0.866, 0.910 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 26008, 4867, 2916 |
Rint | 0.043 |
(sin θ/λ)max (Å−1) | 0.658 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.036, 0.076, 1.42 |
No. of reflections | 4867 |
No. of parameters | 268 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.20, −0.25 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
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.
Complexes of Schiff bases with paramagnetic metal ions have received the much attention as a new class of potential magnetic resonance imaging (MRI) contrast agent [Sesser et al., 1993; Smith et al., 1989]. In addition, a great many Schiff base complexes with metals have also provoked wide interest because they possess a diverse spectrum of biological and pharmaceutical activities and catalytic properties, such as antitumor and antioxidative activities, as well as the inhibition of lipid peroxidation and so on [Padhy et al., 1985; Yu et al., 1993; Wu et al., 1993]. In this paper, we report the synthesis and crystal structure of the title compound, (I), containing β-ketoamine ligand with organic fluorine based on pyrazolone derivatives.
The molecular structure of (I) is shown in Fig. 1. The molecule has approximate twofold rotation symmetry. The NiII ion is in a distorted square-planar coordination geometry which is different from other square-planar geometry (Wang, 2006; Li & Wang, 2007) and is coordinated by two N atoms of imine and two O atoms of pyrazoylone from two Schiff base ligands L. The geometry is distorted towards tetrahedral. The bond angles around NiII center range from 96.63 (5) to 146.30 (8)° and the Ni—N [1.951 (1) Å] and Ni—O [1.924 (1) Å] bond lengths in (I) are in the expected range for such complexes (Zhao, 2007; Peng et al., 2006).
In the crystal structure of (I), the exocyclic C═O bond [1.284 (2) Å for C9═O1] is lengthened relative to that in the free ligand [1.252 (3) Å; Xu et al., 2006], indicating the ligands in the complex have partially changed into enol form from keto form. Mean devation of 0.049 Å from the least-square plane defined by the nine constituent atoms (Ni O1 C9 N1 N2 C7 C8 C11 N3). The pyrazolone ring is nearly coplanar with the C1—C6 benzene ring and nearly perpendicular to the other two benzene rings (C12—C17 and C19–C24); the dihedral angles are 40.54 (5), 87.78 (5) and 80.99 (5)°, respectively. There are no significant intermolecular interactions in the crystal structure.
The structures of metal complexes with ligands in which the 4-fluorophenyl group of L is replaced by Ph in Cu(L1)2 (distorted square-planar coordination geometry; Bao et al., 2005) and Co(L2)2 (distorted tetrahedral coordination geometry; Ma et al., 2006) have been reported.