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A novel complex has been prepared using the (
E)-4-nitro-
N-(pyridin-2-ylmethylidene)aniline bidentate Schiff base ligand and PtCl
2, namely, dichlorido[(
E)-4-nitro-
N-(pyridin-2-ylmethylidene)aniline-κ
2N,
N′]platinum(II) acetonitrile hemisolvate, [PtCl
2(C
12H
9N
3O
2)]·0.5CH
3CN,
1. According to the X-ray measurements of the crystal structure, the Pt
II ion adopts a PtCl
2N
2 square-planar coordination. The coordination of the Schiff base ligand to the Pt
II ion occurs in a cyclic bidentate fashion, as a result of which a five-membered metallacycle is formed. Furthermore, in the structure of
1, the neutral molecules form a one-dimensional chain structure through C—H
Cl and C—H
O hydrogen bonds. The characterization of the complex was performed
via single-crystal X-ray diffraction, IR spectroscopy and elemental analysis, and the antioxidant activity of the complex was evaluated using spectrophotometry by the 1,1-diphenyl-2-picrylhydrazyl (DPPH) method.
Supporting information
CCDC reference: 1544210
Data collection: COLLECT (Nonius, 2002); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2020); software used to prepare material for publication: SHELXL.
Dichlorido[(
E)-4-nitro-
N-(pyridin-2-ylmethylidene)aniline]platinum(II) acetonitrile hemisolvate
top
Crystal data top
[PtCl2(C12H9N3O2)]·0.5C2H3N | Dx = 2.293 Mg m−3 |
Mr = 513.74 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, C2221 | Cell parameters from 15181 reflections |
a = 7.4469 (2) Å | θ = 2.8–27.5° |
b = 27.9271 (11) Å | µ = 9.80 mm−1 |
c = 14.3092 (5) Å | T = 147 K |
V = 2975.89 (18) Å3 | Needle, red |
Z = 8 | 0.10 × 0.06 × 0.06 mm |
F(000) = 1928 | |
Data collection top
Nonius KappaCCD diffractometer | 3418 independent reflections |
Radiation source: fine-focus sealed tube | 2830 reflections with I > 2σ(I) |
Detector resolution: 9 pixels mm-1 | Rint = 0.072 |
φ scans and ω scans with κ offsets | θmax = 27.5°, θmin = 2.8° |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | h = −9→9 |
Tmin = 0.385, Tmax = 0.570 | k = −36→36 |
15181 measured reflections | l = −18→18 |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.039 | w = 1/[σ2(Fo2) + (0.0106P)2 + 24.5578P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.069 | (Δ/σ)max < 0.001 |
S = 1.08 | Δρmax = 1.78 e Å−3 |
3418 reflections | Δρmin = −0.81 e Å−3 |
227 parameters | Absolute structure: Flack x determined using 1041 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al., 2013) |
30 restraints | Absolute structure parameter: −0.030 (8) |
Primary atom site location: structure-invariant direct methods | |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. X-ray diffraction data were measured at 147K with a Mo K? radiation (? = 0.7107
) using a Rigaku SuperNova E (dual source) four-circle diffractometer equipped
with an Eos CCD detector. For all operations (data collection, cell
refinement, data reduction, and multi-scan absorption correction), the
CrysAlis PRO software was used (Agilent, 2014). The structure was solved by
direct methods and refined by a full-matrix least-squares technique on F2 data
using SHELXTL programs (Sheldrick, 2015). All non-hydrogen atoms were refined
anisotropically. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Pt1 | 0.31897 (6) | 0.81317 (2) | 0.15900 (3) | 0.02861 (13) | |
Cl1 | 0.3837 (5) | 0.87583 (12) | 0.0619 (2) | 0.0435 (9) | |
Cl2 | 0.4380 (4) | 0.76332 (12) | 0.04850 (19) | 0.0339 (7) | |
O1 | 0.313 (5) | 0.5360 (8) | 0.2850 (18) | 0.065 (7) | 0.60 (4) |
O2 | 0.154 (4) | 0.5415 (8) | 0.155 (2) | 0.070 (7) | 0.60 (4) |
O1A | 0.206 (7) | 0.5368 (14) | 0.274 (3) | 0.066 (8) | 0.40 (4) |
O2A | 0.247 (6) | 0.5498 (11) | 0.131 (2) | 0.066 (9) | 0.40 (4) |
N1 | 0.2324 (12) | 0.8557 (4) | 0.2639 (6) | 0.028 (2) | |
N2 | 0.2458 (11) | 0.7621 (3) | 0.2534 (6) | 0.022 (2) | |
N3 | 0.2263 (18) | 0.5612 (5) | 0.2186 (10) | 0.059 (4) | |
C1 | 0.2284 (17) | 0.9030 (5) | 0.2676 (9) | 0.041 (3) | |
H1A | 0.264033 | 0.920798 | 0.214200 | 0.049* | |
C2 | 0.1730 (18) | 0.9275 (4) | 0.3478 (9) | 0.043 (3) | |
H2A | 0.173181 | 0.961510 | 0.348509 | 0.051* | |
C3 | 0.1189 (17) | 0.9029 (5) | 0.4249 (9) | 0.042 (3) | |
H3A | 0.077882 | 0.919350 | 0.478955 | 0.051* | |
C4 | 0.1249 (16) | 0.8529 (4) | 0.4229 (8) | 0.032 (3) | |
H4A | 0.090668 | 0.834780 | 0.476228 | 0.039* | |
C5 | 0.1813 (15) | 0.8303 (3) | 0.3423 (8) | 0.029 (2) | |
C6 | 0.1893 (14) | 0.7798 (4) | 0.3320 (7) | 0.027 (2) | |
H6A | 0.153921 | 0.759318 | 0.381733 | 0.032* | |
C8 | 0.3035 (14) | 0.6822 (4) | 0.3167 (7) | 0.031 (2) | |
H8A | 0.346746 | 0.696473 | 0.372599 | 0.037* | |
C9 | 0.2971 (17) | 0.6333 (4) | 0.3091 (8) | 0.036 (3) | |
H9A | 0.333057 | 0.613405 | 0.359668 | 0.043* | |
C10 | 0.2366 (16) | 0.6133 (4) | 0.2253 (9) | 0.034 (3) | |
C11 | 0.1787 (16) | 0.6409 (4) | 0.1522 (8) | 0.034 (2) | |
H11A | 0.134526 | 0.626370 | 0.096726 | 0.041* | |
C12 | 0.1855 (13) | 0.6899 (4) | 0.1604 (7) | 0.028 (2) | |
H12A | 0.148294 | 0.709494 | 0.109675 | 0.034* | |
C13 | 0.2472 (14) | 0.7110 (4) | 0.2433 (8) | 0.027 (3) | |
C1S | −0.398 (3) | 1.003 (5) | 0.503 (13) | 0.060 (10) | 0.5 |
H1S1 | −0.463091 | 0.972649 | 0.492814 | 0.090* | 0.5 |
H1S2 | −0.413320 | 1.023625 | 0.448778 | 0.090* | 0.5 |
H1S3 | −0.446101 | 1.018662 | 0.558883 | 0.090* | 0.5 |
C2S | −0.214 (4) | 0.9929 (19) | 0.516 (4) | 0.065 (10) | 0.5 |
N1S | −0.059 (4) | 0.9897 (12) | 0.537 (2) | 0.081 (10) | 0.5 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Pt1 | 0.0293 (2) | 0.0323 (2) | 0.02423 (19) | 0.0004 (2) | −0.0009 (2) | 0.0042 (2) |
Cl1 | 0.054 (2) | 0.038 (2) | 0.0379 (18) | 0.0005 (15) | 0.0075 (15) | 0.0145 (16) |
Cl2 | 0.0364 (17) | 0.0437 (19) | 0.0216 (15) | 0.0011 (14) | 0.0008 (12) | 0.0010 (13) |
O1 | 0.11 (2) | 0.027 (9) | 0.061 (12) | 0.004 (15) | −0.009 (16) | 0.006 (8) |
O2 | 0.110 (18) | 0.036 (10) | 0.066 (14) | −0.025 (11) | −0.021 (14) | −0.003 (11) |
O1A | 0.11 (2) | 0.039 (13) | 0.046 (13) | −0.010 (19) | −0.014 (19) | 0.011 (11) |
O2A | 0.11 (2) | 0.023 (14) | 0.069 (18) | 0.009 (14) | 0.051 (16) | 0.022 (12) |
N1 | 0.032 (6) | 0.027 (6) | 0.025 (5) | 0.008 (4) | −0.006 (4) | 0.003 (4) |
N2 | 0.019 (5) | 0.033 (6) | 0.014 (5) | −0.004 (4) | −0.003 (4) | 0.001 (4) |
N3 | 0.065 (9) | 0.050 (8) | 0.062 (9) | −0.002 (7) | 0.025 (8) | 0.005 (8) |
C1 | 0.046 (9) | 0.044 (9) | 0.033 (7) | 0.004 (6) | −0.002 (6) | 0.006 (6) |
C2 | 0.053 (7) | 0.036 (7) | 0.039 (7) | −0.001 (7) | 0.002 (9) | −0.001 (6) |
C3 | 0.045 (8) | 0.046 (9) | 0.036 (7) | 0.009 (6) | −0.008 (6) | −0.011 (7) |
C4 | 0.036 (7) | 0.035 (8) | 0.026 (6) | −0.006 (6) | −0.007 (5) | 0.004 (6) |
C5 | 0.028 (5) | 0.031 (6) | 0.027 (5) | 0.001 (5) | 0.012 (7) | 0.000 (5) |
C6 | 0.019 (5) | 0.041 (6) | 0.019 (5) | −0.005 (5) | −0.010 (6) | 0.007 (5) |
C8 | 0.026 (5) | 0.037 (6) | 0.029 (6) | 0.001 (6) | −0.004 (5) | 0.004 (5) |
C9 | 0.041 (7) | 0.035 (7) | 0.033 (7) | 0.001 (6) | 0.008 (6) | 0.005 (5) |
C10 | 0.041 (8) | 0.028 (7) | 0.035 (7) | −0.007 (5) | 0.009 (5) | 0.001 (6) |
C11 | 0.031 (5) | 0.034 (6) | 0.038 (6) | −0.005 (6) | 0.003 (8) | −0.004 (6) |
C12 | 0.024 (4) | 0.038 (6) | 0.023 (4) | 0.003 (6) | 0.002 (5) | 0.004 (6) |
C13 | 0.029 (6) | 0.031 (7) | 0.020 (6) | −0.006 (5) | 0.002 (4) | 0.008 (5) |
C1S | 0.077 (14) | 0.02 (3) | 0.08 (2) | −0.01 (3) | 0.00 (3) | −0.004 (15) |
C2S | 0.073 (15) | 0.03 (2) | 0.09 (2) | −0.015 (18) | 0.00 (2) | −0.035 (16) |
N1S | 0.069 (16) | 0.07 (2) | 0.10 (3) | −0.010 (16) | 0.003 (16) | −0.055 (19) |
Geometric parameters (Å, º) top
Pt1—N1 | 2.021 (10) | C4—C5 | 1.381 (15) |
Pt1—N2 | 2.039 (9) | C4—H4A | 0.9500 |
Pt1—Cl1 | 2.286 (3) | C5—C6 | 1.418 (14) |
Pt1—Cl2 | 2.286 (3) | C6—H6A | 0.9500 |
O1—N3 | 1.35 (3) | C8—C9 | 1.372 (16) |
O2—N3 | 1.19 (2) | C8—C13 | 1.389 (15) |
O1A—N3 | 1.06 (4) | C8—H8A | 0.9500 |
O2A—N3 | 1.30 (4) | C9—C10 | 1.397 (16) |
N1—C1 | 1.320 (15) | C9—H9A | 0.9500 |
N1—C5 | 1.382 (14) | C10—C11 | 1.369 (16) |
N2—C6 | 1.298 (13) | C11—C12 | 1.375 (15) |
N2—C13 | 1.434 (15) | C11—H11A | 0.9500 |
N3—C10 | 1.459 (18) | C12—C13 | 1.403 (15) |
C1—C2 | 1.399 (17) | C12—H12A | 0.9500 |
C1—H1A | 0.9500 | C1S—C2S | 1.41 (5) |
C2—C3 | 1.361 (17) | C1S—H1S1 | 0.9800 |
C2—H2A | 0.9500 | C1S—H1S2 | 0.9800 |
C3—C4 | 1.397 (17) | C1S—H1S3 | 0.9800 |
C3—H3A | 0.9500 | C2S—N1S | 1.19 (4) |
| | | |
N1—Pt1—N2 | 80.4 (4) | C4—C5—C6 | 123.7 (11) |
N1—Pt1—Cl1 | 93.9 (3) | N1—C5—C6 | 114.6 (10) |
N2—Pt1—Cl1 | 174.1 (3) | N2—C6—C5 | 118.8 (10) |
N1—Pt1—Cl2 | 174.9 (3) | N2—C6—H6A | 120.6 |
N2—Pt1—Cl2 | 97.8 (3) | C5—C6—H6A | 120.6 |
Cl1—Pt1—Cl2 | 87.94 (12) | C9—C8—C13 | 120.5 (11) |
C1—N1—C5 | 118.4 (10) | C9—C8—H8A | 119.8 |
C1—N1—Pt1 | 128.7 (9) | C13—C8—H8A | 119.8 |
C5—N1—Pt1 | 112.8 (7) | C8—C9—C10 | 118.5 (11) |
C6—N2—C13 | 118.0 (9) | C8—C9—H9A | 120.8 |
C6—N2—Pt1 | 113.3 (8) | C10—C9—H9A | 120.8 |
C13—N2—Pt1 | 128.8 (7) | C11—C10—C9 | 122.2 (12) |
O1A—N3—O2A | 126 (3) | C11—C10—N3 | 119.6 (12) |
O2—N3—O1 | 120.8 (19) | C9—C10—N3 | 118.1 (12) |
O1A—N3—C10 | 127 (3) | C10—C11—C12 | 118.9 (11) |
O2—N3—C10 | 122.3 (17) | C10—C11—H11A | 120.5 |
O2A—N3—C10 | 107.6 (19) | C12—C11—H11A | 120.5 |
O1—N3—C10 | 116.8 (16) | C11—C12—C13 | 120.2 (11) |
N1—C1—C2 | 121.9 (12) | C11—C12—H12A | 119.9 |
N1—C1—H1A | 119.0 | C13—C12—H12A | 119.9 |
C2—C1—H1A | 119.0 | C8—C13—C12 | 119.7 (11) |
C3—C2—C1 | 120.3 (12) | C8—C13—N2 | 120.1 (10) |
C3—C2—H2A | 119.8 | C12—C13—N2 | 120.2 (10) |
C1—C2—H2A | 119.8 | C2S—C1S—H1S1 | 109.5 |
C2—C3—C4 | 118.6 (12) | C2S—C1S—H1S2 | 109.5 |
C2—C3—H3A | 120.7 | H1S1—C1S—H1S2 | 109.5 |
C4—C3—H3A | 120.7 | C2S—C1S—H1S3 | 109.5 |
C5—C4—C3 | 119.0 (11) | H1S1—C1S—H1S3 | 109.5 |
C5—C4—H4A | 120.5 | H1S2—C1S—H1S3 | 109.5 |
C3—C4—H4A | 120.5 | N1S—C2S—C1S | 171 (9) |
C4—C5—N1 | 121.7 (10) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1A···Cl1 | 0.95 | 2.67 | 3.252 (14) | 120 |
C2—H2A···O2i | 0.95 | 2.58 | 3.44 (3) | 150 |
C2—H2A···O2Ai | 0.95 | 2.55 | 3.48 (3) | 165 |
C4—H4A···Cl2ii | 0.95 | 2.94 | 3.739 (13) | 143 |
C6—H6A···Cl2ii | 0.95 | 2.56 | 3.456 (11) | 157 |
C8—H8A···Cl2iii | 0.95 | 2.71 | 3.544 (12) | 147 |
C11—H11A···Cl1iv | 0.95 | 2.94 | 3.799 (13) | 151 |
C12—H12A···Cl2iv | 0.95 | 2.86 | 3.746 (11) | 157 |
C1S—H1S1···Cl1v | 0.98 | 2.88 | 3.67 (14) | 138 |
C1S—H1S3···Cl1vi | 0.98 | 2.98 | 3.50 (14) | 114 |
C1S—H1S2···O2vii | 0.97 | 2.38 | 3.15 (15) | 135 |
Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) −x+1/2, −y+3/2, z+1/2; (iii) −x+1, y, −z+1/2; (iv) x−1/2, −y+3/2, −z; (v) −x, y, −z+1/2; (vi) −x, −y+2, z+1/2; (vii) −x−1/2, y+1/2, −z+1/2. |
Radical scavenging abilities (IC50±SD, µM) of compound
1 and standard drugs [What does * represent] topCompound | DPPH radical scavenging activity | | ABTS radical scavenging activity | |
| IC50 (µM) | R2 | IC50 (µM) | R2 |
PtII complex | 1.98±1.05 | 0.991 | 4.27±1.17 | 0.808 |
Rutin* | 2.52±1.60 | 0.798 | 2.83±1.84 | 0.983 |
Vitamin C* | 1.92±1.07 | 0.978 | - | - |
BHT* | - | - | 1.64±1.54 | 0.919 |
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