research communications
Crystal structures of organoplatinum complexes containing alkyleugenoxyacetate and p-chloroaniline
aChemistry Department, Hanoi National University of Education, 136 - Xuan Thuy - Cau Giay, Hanoi, Vietnam, and bKU Leuven - University of Leuven, Department of Chemistry, Celestijnenlaan 200F - bus 2404, B-3001 Heverlee, Belgium
*Correspondence e-mail: luc.vanmeervelt@kuleuven.be
In the title complexes, trans-dichlorido(4-chloroaniline-κN){3-methoxy-4-methoxycarbonylmethoxy-1-[(2,3-η)-prop-2-en-1-yl]benzene}platinum(II) 0.1-hydrate, [PtCl2(C6H6ClN)(C13H16O4)]·0.1H2O, (I), and trans-dichlorido(4-chloroaniline-κN){4-ethoxycarbonylmethoxy-3-methoxy-1-[(2,3-η)-prop-2-en-1-yl]benzene}platinum(II), [PtCl2(C6H6ClN)(C14H18O4)], (II), the PtII metal atom displays a slightly distorted square-planar coordination geometry defined by the aniline N atom, two chloride anions (trans-positioned) and one ethylenic double bond. The least-squares planes through the two aromatic ring systems make an angle of 47.3 (3)° for (I) and 38.6 (2)° for (II). Both structures show disorder for the PtCl2 fragment, in the case of (I) even further extended towards the CH2—CH=CH2 ligand. An intramolecular C—H⋯Cl hydrogen bond occurs in (I). In the crystal packing of (I), which is dominated by N—H⋯O and C—H⋯Cl interactions, a partially occupied water molecule is observed on a twofold rotation axis with a refined site occupancy of 0.10 (1). A C—H⋯π interaction is also present. In (II), inversion dimers form chains along the b-axis direction by N—H⋯O hydrogen bonds.
1. Chemical context
Complexes of platinum(II) such as cisplatin, carboplatin and oxaliplatin have been known to exhibit inhibitory activities on several human cancer cells and are widely used in pharmacy (Zhang et al., 2006). However, many side effects and drug-resistant phenomena have been reported for the use of these complexes (Von Hoff et al., 1979; Coates et al., 1983; Griffin et al., 1996). Therefore, it is necessary to design new complexes with high activities but low toxicity (Chabner & Roberts, 2005; Johnstone et al., 2014). For this purpose, we have recently synthesized several PtII complexes containing natural arylolefines as ligand, i.e. derivatives of eugenol (4-allyl-2-methoxylphenol) such as methyleugenol and alkyleugenoxyacetate, with high toxicity towards human cancerous cells (IC50 values < 5 µg/mL; Da et al., 2012; Da, Chi et al., 2015; Da, Hai et al., 2015). Interestingly, these complexes represent special arrangements in which the PtII atoms are coordinated by arylolefines through the C=C bond of the allyl group. Complexes of PtII containing methyl- or ethyleugenoxylacetate and p-chloroaniline were synthesized and their crystal and molecular structures characterized and reported here.
2. Structural commentary
The complexes crystallize in different space groups, C2/c for the methyleugenoxyacetate derivative (I) and P for the ethyleugenoxyacetate derivative (II). The central PtII metal atom displays a distorted square-planar coordination with the PtII atom coordinated by two Cl atoms, the NH2-group of p-chloroaniline and the C=C double bond of the eugenol ligand. In both complexes, the Cl atoms are trans with respect to each other (Fig. 1). The eugenol ligand only interacts via the C=C double bond and not by a C atom of the phenyl ring. Both structures show some disorder of the PtII atom and its environment. In (I) the PtCl2CH2=CH—CH2 fragment is disordered over two positions [population parameters 0.679 (8) and 0.321 (8)], while in (II) only the PtCl2 fragment is disordered over two positions [population parameters 0.872 (6) and 0.128 (6)]. The angles between the best planes through the two aromatic rings are 47.3 (3) and 38.6 (2)° for (I) and (II), respectively. An intramolecular C—H⋯Cl interaction is observed for (II) with a H26A⋯Cl9 distance of 2.73 Å. In (I) the shortest intramolecular H⋯Cl contact distance is 3.13 Å for H29A⋯Cl9.
3. Supramolecular features
The crystal packing of (I) is built up by N—H⋯O and C—H⋯Cl interactions (Table 1, Fig. 2). A water molecule O34 was identified at a special position [on a twofold rotation axis, occupancy factor 0.10 (1)] where it interacts with atoms N2, O28 and O31 linking four molecules together (Fig. 3).
The crystal packing of (II) is dominated by hydrogen-bonding interactions (Table 2). Inversion dimers created by N2—H2AB⋯O28i hydrogen bonds are further linked into chains in the b-axis direction by N2—H2AA⋯(O23ii,O25ii) hydrogen bonds [Figs. 4 and 5; symmetry codes: (i) − x + 1, −y, − z + 1; (ii) x, y + 1, z].
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No π–π interactions are observed in the packing of either structure. For (I) a C—H⋯π interaction is present [C27—H27B⋯Cg1iii, H27B⋯Cg1iii = 2.72 Å; Cg1 is the centroid of the C20-C25 ring; symmetry code: (iii) −x + 1, y, −z + ].
4. Database survey
The Pt—N distances in (I) and (II) vary from 2.033 (6) to 2.273 (8) Å and deviate for the minor parts (Pt1B) due to the disorder from the average Pt—N distance of 2.09 (5) Å for Pt—NH2—phenyl fragments present in the Cambridge Structural Database (CSD, Version 5.37; Groom et al., 2016). The Pt1A—Cl distances are between 2.288 (4) and 2.305 (2) Å and agree well with the average Pt—Cl distance of 2.32 (3) Å for trans complexes present in the CSD. One Pt1B—Cl distance [2.151 (2) Å] deviates significantly from this average.
A search in the CSD for Pt complexes with Pt coordinated by Cl, NH2 and C=C shows 11 hits. As fourth ligand we notice an additional Cl atom (eight hits, five trans and three cis coordinations) or C atom (two hits) or O atom (one hit). In the complex [PtCl(methyleugenol)(o-toluidine)] (CSD refcode GOYJEL; Da, Chi et al., 2015), the central Pt atom coordinated by only one Cl atom, the NH2 group of o-toluidine, the C=C double bond of the eugenol ligand and also a C atom of the eugenol ligand. In (I) and (II) this last interaction is not present and is replaced by an additional Cl atom.
5. Synthesis and crystallization
Synthesis of K[Pt(Alkeug)Cl3]:
The mononuclear complexes K[Pt(Alkeug)Cl3] (Alkeug are methyleugenoxylacetate or Meteug, and ethyleugenoxylacetate or Eteug) were synthesized following the protocol of Da and coworkers (Da et al., 2012; Da, Chi et al., 2015; Da, Hai et al., 2015).
Synthesis of trans-[PtCl2(Alkeug)(C6H6NCl)]:
A solution of 127.0 mg (1.0 mmol) p-chloroaniline in 10 mL acetone/ethanol (1:1 v/v) was added to a mixture of 1.0 mmol [K[Pt(Alkeug)Cl3] and 10 mL acetone/ethanol (1:1 v/v). After two h stirring, a white precipitate of KCl was separated out. The remaining solution was stirred for two h at room temperature to obtain a yellow precipitate, which was collected by filtration, washed with ethanol and diethyl ether and dried in vacuum. The obtained crystals are soluble in chloroform and acetone, slightly soluble in ethanol and insoluble in water. The yield was 70–80%. Single crystals suitable for X-ray investigation were obtained by slow evaporation from a chloroform/ethanol (1:2 v/v) solution at room temperature.
Data for [PtCl2(Meteug)(C6H6NCl)] (I):
IR (Impack-410 Nicolet spectrometer, KBr, cm−1): 3243, 3164 (νNH); 3060, 2958, 2836 (νCH); 1746 (νC=O); 1592, 1517 (aromatic, νC=C, νC=N); 545 (νPt-N).
1H NMR (δ p.p.m; 500 MHz, CDCl3): 3.07 (br, 1H, –CH2a); 3.40 (dd, 2J = 15.0 Hz, 3J = 8.0 Hz, –CH2b); 5.54 (br, 1H, allyl); 4.54 (br, 1H, cis-alkene); 4.65 (d, J = 13.0 Hz, 1H, trans-alkene); 6.85 (ov, 1H, Ar); 6.83 (ov, 1H, Ar); 6.71 (d, J = 8.0 Hz, 1H, Ar); 3.82 (ov, 3H, –OCH3); 4.69 (s, 2H, –CH2–); 7.32 (ov, 4H, Ar), 6.10 (br, NH2).
Data for [PtCl2(Eteug)(C6H6NCl)] (II):
IR (KBr, cm−1): 3239, 3160 (νNH); 3060, 2921, 2823 (νCH); 1746 (νC=O); 1595, 1516 (aromatic, νC=C, νC=N); 550 (νPt-N).
1H NMR (δ p.p.m; 500 MHz, CDCl3): 3.08 (br, 1H, –CH2a); 3.39 (dd, 2J = 15.5 Hz, 3J = 7.5 Hz, 1H, –CH2b); 5.53 (br, 1H, allyl); 4.63 (d, J = 9.5 Hz, 1H, cis-alkene); 4.52 (br, 1H, trans-alkene); 6.78 (ov, 1H, Ar); 6.82 (d, J = 8.0 Hz, 1H, Ar); 6.70 (d, J = 8.0 Hz, 1H, Ar); 3.82 (s, 3H, –OCH3); 4.28 (q, J = 7.0 Hz, 2H, –CH2); 1.30 (t, J = 7.0 Hz, 3H, –CH3); 4.67 (s, 2H, –CH2–); 7.30 (ov, 4H, Ar), 6.20 (br, NH2).
6. Refinement
Crystal data, data collection and structure . Both structures show disorder which was modelled as good as possible, but still some larger peaks are present in the difference maps.
details are summarized in Table 3
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In (I) the PtCl2CH2=CH—CH2 fragment is disordered over two positions [population parameters 0.679 (8) and 0.321 (8)] and refined with constraints for the bond lengths present in this fragment. of the population parameter of oxygen atom O34 (at special position) converged to 0.10 (1). Water H atoms were not located.
In (II) only the PtCl2 fragment is disordered over two positions [population parameters 0.872 (6) and 0.128 (6)].
All H atoms were placed in idealized positions and refined in riding mode, with Uiso(H) values assigned as 1.2Ueq of the parent atoms (1.5 times for methyl groups), with C—H distances of 0.95 (aromatic and =CH2), 0.98 (CH3), 0.99 (CH2) and 1.00 Å (CH), and N—H distances of 0.91 Å (NH2). Enhanced rigid bond restraints were used for the anisotropic temperature factors of the non-H atoms. In the final cycles of 7 and 15 outliers were omitted for (I) and (II), respectively.
Supporting information
https://doi.org/10.1107/S2056989016008872/rz5189sup1.cif
contains datablocks I, II. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989016008872/rz5189Isup2.hkl
Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S2056989016008872/rz5189IIsup3.hkl
For both compounds, data collection: CrysAlis PRO (Agilent, 2012); cell
CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012). Program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) for (I); olex2.solve (Bourhis et al., 2015) for (II). For both compounds, program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).[PtCl2(C6H6ClN)(C13H16O4)]·0.1H2O | F(000) = 2440.0 |
Mr = 631.61 | Dx = 1.997 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 13.8322 (6) Å | Cell parameters from 22209 reflections |
b = 15.0753 (4) Å | θ = 3.3–28.6° |
c = 21.0367 (9) Å | µ = 7.09 mm−1 |
β = 106.683 (5)° | T = 100 K |
V = 4202.0 (3) Å3 | Block, yellow |
Z = 8 | 0.2 × 0.1 × 0.1 mm |
Agilent SuperNova diffractometer (single source at offset, Eos detector) | 4295 independent reflections |
Radiation source: SuperNova (Mo) X-ray Source | 4033 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.032 |
Detector resolution: 15.9631 pixels mm-1 | θmax = 26.4°, θmin = 2.9° |
ω scans | h = −17→17 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) | k = −18→18 |
Tmin = 0.715, Tmax = 1.000 | l = −26→26 |
44052 measured reflections |
Refinement on F2 | Primary atom site location: heavy-atom method |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.032 | H-atom parameters constrained |
wR(F2) = 0.064 | w = 1/[σ2(Fo2) + 46.5817P] where P = (Fo2 + 2Fc2)/3 |
S = 1.22 | (Δ/σ)max < 0.001 |
4295 reflections | Δρmax = 1.28 e Å−3 |
315 parameters | Δρmin = −0.92 e Å−3 |
291 restraints |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Pt1A | 0.75061 (14) | 0.49179 (7) | 0.82720 (10) | 0.0213 (2) | 0.679 (8) |
Pt1B | 0.7676 (3) | 0.4904 (2) | 0.8417 (2) | 0.0349 (6) | 0.321 (8) |
N2 | 0.8940 (3) | 0.5396 (3) | 0.8235 (2) | 0.0369 (10) | |
H2AA | 0.9427 | 0.4996 | 0.8432 | 0.044* | 0.679 (8) |
H2AB | 0.8938 | 0.5459 | 0.7805 | 0.044* | 0.679 (8) |
H2BC | 0.9465 | 0.5015 | 0.8389 | 0.044* | 0.321 (8) |
H2BD | 0.8835 | 0.5469 | 0.7791 | 0.044* | 0.321 (8) |
C3 | 0.9164 (4) | 0.6242 (3) | 0.8573 (3) | 0.0328 (11) | |
C4 | 0.9600 (5) | 0.6278 (4) | 0.9245 (3) | 0.0457 (14) | |
H4 | 0.9792 | 0.5743 | 0.9487 | 0.055* | |
C5 | 0.9763 (5) | 0.7077 (4) | 0.9572 (3) | 0.0491 (15) | |
H5 | 1.0047 | 0.7096 | 1.0040 | 0.059* | |
C6 | 0.9509 (4) | 0.7856 (4) | 0.9213 (3) | 0.0390 (12) | |
C7 | 0.9087 (4) | 0.7838 (4) | 0.8539 (3) | 0.0327 (11) | |
H7 | 0.8915 | 0.8374 | 0.8295 | 0.039* | |
C8 | 0.8913 (4) | 0.7023 (3) | 0.8218 (3) | 0.0303 (11) | |
H8 | 0.8621 | 0.7002 | 0.7751 | 0.036* | |
Cl9 | 0.97029 (14) | 0.88741 (11) | 0.96197 (8) | 0.0557 (4) | |
Cl10 | 0.8612 (7) | 0.4286 (5) | 0.9395 (3) | 0.0395 (16) | 0.321 (8) |
Cl11 | 0.6918 (4) | 0.5297 (5) | 0.7175 (2) | 0.0425 (11) | 0.679 (8) |
Cl12 | 0.8205 (3) | 0.4484 (2) | 0.93519 (14) | 0.0337 (6) | 0.679 (8) |
Cl13 | 0.6770 (6) | 0.5272 (9) | 0.7318 (4) | 0.036 (2) | 0.321 (8) |
C14 | 0.6190 (7) | 0.4194 (5) | 0.8275 (4) | 0.0265 (19) | 0.679 (8) |
H14A | 0.6296 | 0.3818 | 0.8652 | 0.032* | 0.679 (8) |
H14B | 0.6241 | 0.3962 | 0.7867 | 0.032* | 0.679 (8) |
C15 | 0.5959 (5) | 0.5080 (4) | 0.8322 (3) | 0.0213 (15) | 0.679 (8) |
H15 | 0.5489 | 0.5324 | 0.7905 | 0.026* | 0.679 (8) |
C16 | 0.5856 (7) | 0.5525 (4) | 0.8945 (4) | 0.0271 (18) | 0.679 (8) |
H16A | 0.6411 | 0.5339 | 0.9335 | 0.032* | 0.679 (8) |
H16B | 0.5205 | 0.5363 | 0.9022 | 0.032* | 0.679 (8) |
C17 | 0.6445 (18) | 0.4012 (12) | 0.8481 (11) | 0.041 (5) | 0.321 (8) |
H17A | 0.5949 | 0.3889 | 0.8073 | 0.050* | 0.321 (8) |
H17B | 0.6967 | 0.3596 | 0.8662 | 0.050* | 0.321 (8) |
C18 | 0.6407 (13) | 0.4798 (11) | 0.8811 (10) | 0.046 (4) | 0.321 (8) |
H18 | 0.6633 | 0.4711 | 0.9302 | 0.055* | 0.321 (8) |
C19 | 0.5657 (13) | 0.5548 (7) | 0.8620 (10) | 0.042 (4) | 0.321 (8) |
H19A | 0.5071 | 0.5376 | 0.8774 | 0.051* | 0.321 (8) |
H19B | 0.5416 | 0.5552 | 0.8129 | 0.051* | 0.321 (8) |
C20 | 0.5902 (4) | 0.6522 (4) | 0.8837 (3) | 0.0424 (13) | |
C21 | 0.5064 (4) | 0.7011 (3) | 0.8465 (3) | 0.0339 (11) | |
H21 | 0.4456 | 0.6712 | 0.8242 | 0.041* | |
C22 | 0.5118 (4) | 0.7926 (3) | 0.8422 (2) | 0.0282 (10) | |
C23 | 0.6008 (4) | 0.8361 (3) | 0.8764 (3) | 0.0313 (11) | |
C24 | 0.6828 (4) | 0.7872 (4) | 0.9122 (3) | 0.0395 (12) | |
H24 | 0.7435 | 0.8167 | 0.9352 | 0.047* | |
C25 | 0.6774 (4) | 0.6956 (4) | 0.9150 (3) | 0.0440 (13) | |
H25 | 0.7349 | 0.6627 | 0.9389 | 0.053* | |
O26 | 0.4355 (3) | 0.8454 (2) | 0.80566 (18) | 0.0324 (8) | |
C27 | 0.3460 (4) | 0.8027 (4) | 0.7673 (3) | 0.0343 (12) | |
H27A | 0.3117 | 0.7750 | 0.7970 | 0.051* | |
H27B | 0.3635 | 0.7571 | 0.7393 | 0.051* | |
H27C | 0.3012 | 0.8465 | 0.7393 | 0.051* | |
O28 | 0.5993 (3) | 0.9267 (2) | 0.86886 (19) | 0.0372 (9) | |
C29 | 0.6894 (5) | 0.9716 (4) | 0.9030 (3) | 0.0446 (14) | |
H29A | 0.7479 | 0.9457 | 0.8914 | 0.054* | |
H29B | 0.7014 | 0.9667 | 0.9515 | 0.054* | |
C30 | 0.6754 (5) | 1.0688 (4) | 0.8813 (3) | 0.0480 (14) | |
O31 | 0.6176 (4) | 1.0965 (3) | 0.8301 (3) | 0.0582 (12) | |
O32 | 0.7487 (5) | 1.1132 (3) | 0.9246 (2) | 0.0740 (16) | |
C33 | 0.7493 (9) | 1.2074 (5) | 0.9135 (5) | 0.102 (3) | |
H33A | 0.7428 | 1.2188 | 0.8666 | 0.154* | |
H33B | 0.8128 | 1.2327 | 0.9410 | 0.154* | |
H33C | 0.6926 | 1.2349 | 0.9253 | 0.154* | |
O34 | 1.0000 | 0.5000 | 0.7500 | 0.10 (2) | 0.10 (1) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Pt1A | 0.0216 (4) | 0.0167 (3) | 0.0252 (5) | −0.00062 (18) | 0.0064 (4) | −0.0012 (2) |
Pt1B | 0.0269 (10) | 0.0479 (9) | 0.0288 (12) | −0.0027 (5) | 0.0061 (9) | −0.0021 (6) |
N2 | 0.028 (2) | 0.029 (2) | 0.054 (3) | 0.0035 (17) | 0.0125 (19) | 0.0060 (19) |
C3 | 0.022 (2) | 0.033 (2) | 0.043 (3) | −0.0006 (19) | 0.008 (2) | 0.006 (2) |
C4 | 0.045 (3) | 0.039 (3) | 0.046 (3) | −0.014 (2) | 0.001 (2) | 0.013 (2) |
C5 | 0.052 (4) | 0.052 (3) | 0.039 (3) | −0.020 (3) | 0.005 (3) | 0.009 (2) |
C6 | 0.034 (3) | 0.041 (3) | 0.042 (3) | −0.018 (2) | 0.011 (2) | 0.001 (2) |
C7 | 0.027 (3) | 0.033 (2) | 0.040 (3) | −0.003 (2) | 0.012 (2) | 0.008 (2) |
C8 | 0.022 (2) | 0.032 (2) | 0.036 (3) | 0.0006 (19) | 0.008 (2) | 0.0055 (19) |
Cl9 | 0.0722 (11) | 0.0515 (9) | 0.0477 (9) | −0.0338 (8) | 0.0242 (8) | −0.0125 (7) |
Cl10 | 0.049 (4) | 0.037 (3) | 0.029 (2) | −0.003 (3) | 0.005 (3) | 0.008 (2) |
Cl11 | 0.058 (3) | 0.0403 (18) | 0.0382 (14) | 0.0123 (18) | 0.0281 (13) | 0.0128 (11) |
Cl12 | 0.0287 (15) | 0.0273 (13) | 0.0359 (12) | 0.0024 (10) | −0.0052 (11) | 0.0095 (9) |
Cl13 | 0.015 (2) | 0.035 (3) | 0.054 (5) | −0.005 (2) | 0.004 (3) | 0.016 (4) |
C14 | 0.025 (4) | 0.027 (4) | 0.028 (4) | −0.001 (3) | 0.008 (3) | 0.001 (3) |
C15 | 0.015 (3) | 0.027 (3) | 0.020 (3) | 0.000 (2) | 0.002 (2) | 0.003 (2) |
C16 | 0.036 (4) | 0.029 (3) | 0.018 (4) | 0.005 (3) | 0.011 (3) | 0.007 (3) |
C17 | 0.032 (8) | 0.039 (7) | 0.051 (10) | 0.004 (5) | 0.010 (7) | 0.009 (6) |
C18 | 0.042 (7) | 0.041 (6) | 0.058 (9) | 0.002 (5) | 0.019 (6) | 0.010 (6) |
C19 | 0.042 (8) | 0.041 (5) | 0.057 (11) | 0.008 (4) | 0.033 (7) | 0.022 (5) |
C20 | 0.041 (3) | 0.035 (2) | 0.061 (3) | 0.007 (2) | 0.030 (3) | 0.013 (2) |
C21 | 0.030 (2) | 0.030 (2) | 0.049 (3) | 0.0014 (19) | 0.022 (2) | 0.001 (2) |
C22 | 0.031 (2) | 0.028 (2) | 0.030 (2) | 0.0048 (18) | 0.0156 (19) | −0.0011 (18) |
C23 | 0.034 (2) | 0.033 (2) | 0.028 (2) | 0.0011 (19) | 0.012 (2) | 0.0007 (19) |
C24 | 0.037 (3) | 0.047 (3) | 0.034 (3) | 0.002 (2) | 0.010 (2) | 0.006 (2) |
C25 | 0.035 (3) | 0.047 (3) | 0.052 (3) | 0.009 (2) | 0.016 (3) | 0.017 (2) |
O26 | 0.0293 (18) | 0.0261 (17) | 0.040 (2) | 0.0027 (14) | 0.0081 (15) | −0.0015 (15) |
C27 | 0.030 (3) | 0.038 (3) | 0.035 (3) | 0.002 (2) | 0.010 (2) | −0.004 (2) |
O28 | 0.037 (2) | 0.0302 (18) | 0.041 (2) | −0.0044 (15) | 0.0062 (17) | −0.0065 (15) |
C29 | 0.046 (3) | 0.049 (3) | 0.039 (3) | −0.015 (2) | 0.011 (3) | −0.004 (2) |
C30 | 0.061 (4) | 0.042 (3) | 0.050 (3) | −0.017 (3) | 0.029 (3) | −0.005 (2) |
O31 | 0.052 (3) | 0.051 (3) | 0.076 (3) | 0.001 (2) | 0.026 (2) | 0.007 (2) |
O32 | 0.110 (4) | 0.066 (3) | 0.050 (3) | −0.052 (3) | 0.030 (3) | −0.011 (2) |
C33 | 0.171 (10) | 0.062 (4) | 0.100 (7) | −0.063 (5) | 0.081 (7) | −0.018 (4) |
O34 | 0.06 (3) | 0.21 (6) | 0.04 (2) | 0.000 | 0.015 (18) | 0.000 |
Pt1A—N2 | 2.132 (5) | C17—H17A | 0.9500 |
Pt1A—Cl11 | 2.288 (4) | C17—H17B | 0.9500 |
Pt1A—Cl12 | 2.294 (3) | C17—C18 | 1.381 (12) |
Pt1A—C14 | 2.124 (9) | C18—H18 | 1.0000 |
Pt1A—C15 | 2.187 (6) | C18—C19 | 1.508 (11) |
Pt1B—N2 | 2.033 (6) | C19—H19A | 0.9900 |
Pt1B—Cl10 | 2.291 (5) | C19—H19B | 0.9900 |
Pt1B—Cl13 | 2.357 (7) | C19—C20 | 1.546 (11) |
Pt1B—C17 | 2.20 (2) | C20—C21 | 1.407 (8) |
Pt1B—C18 | 2.151 (18) | C20—C25 | 1.364 (9) |
N2—H2AA | 0.9100 | C21—H21 | 0.9500 |
N2—H2AB | 0.9100 | C21—C22 | 1.386 (7) |
N2—H2BC | 0.9100 | C22—C23 | 1.398 (7) |
N2—H2BD | 0.9100 | C22—O26 | 1.369 (6) |
N2—C3 | 1.450 (7) | C23—C24 | 1.381 (8) |
C3—C4 | 1.370 (8) | C23—O28 | 1.374 (6) |
C3—C8 | 1.384 (7) | C24—H24 | 0.9500 |
C4—H4 | 0.9500 | C24—C25 | 1.385 (8) |
C4—C5 | 1.374 (9) | C25—H25 | 0.9500 |
C5—H5 | 0.9500 | O26—C27 | 1.422 (6) |
C5—C6 | 1.386 (8) | C27—H27A | 0.9800 |
C6—C7 | 1.370 (8) | C27—H27B | 0.9800 |
C6—Cl9 | 1.741 (6) | C27—H27C | 0.9800 |
C7—H7 | 0.9500 | O28—C29 | 1.419 (7) |
C7—C8 | 1.389 (7) | C29—H29A | 0.9900 |
C8—H8 | 0.9500 | C29—H29B | 0.9900 |
C14—H14A | 0.9500 | C29—C30 | 1.530 (9) |
C14—H14B | 0.9500 | C30—O31 | 1.218 (8) |
C14—C15 | 1.383 (9) | C30—O32 | 1.332 (8) |
C15—H15 | 1.0000 | O32—C33 | 1.440 (9) |
C15—C16 | 1.514 (8) | C33—H33A | 0.9800 |
C16—H16A | 0.9900 | C33—H33B | 0.9800 |
C16—H16B | 0.9900 | C33—H33C | 0.9800 |
C16—C20 | 1.523 (8) | ||
N2—Pt1A—Cl11 | 86.8 (2) | H16A—C16—H16B | 108.6 |
N2—Pt1A—Cl12 | 90.03 (16) | C20—C16—H16A | 110.4 |
N2—Pt1A—C15 | 153.8 (2) | C20—C16—H16B | 110.4 |
Cl11—Pt1A—Cl12 | 175.35 (16) | Pt1B—C17—H17A | 115.8 |
C14—Pt1A—N2 | 168.7 (2) | Pt1B—C17—H17B | 85.2 |
C14—Pt1A—Cl11 | 94.3 (3) | H17A—C17—H17B | 120.0 |
C14—Pt1A—Cl12 | 88.2 (3) | C18—C17—Pt1B | 69.4 (12) |
C14—Pt1A—C15 | 37.4 (3) | C18—C17—H17A | 120.0 |
C15—Pt1A—Cl11 | 87.2 (2) | C18—C17—H17B | 120.0 |
C15—Pt1A—Cl12 | 97.1 (2) | Pt1B—C18—H18 | 111.2 |
N2—Pt1B—Cl10 | 91.2 (2) | C17—C18—Pt1B | 73.6 (13) |
N2—Pt1B—Cl13 | 88.5 (3) | C17—C18—H18 | 111.2 |
N2—Pt1B—C17 | 162.7 (5) | C17—C18—C19 | 129.1 (17) |
N2—Pt1B—C18 | 160.0 (5) | C19—C18—Pt1B | 114.6 (12) |
Cl10—Pt1B—Cl13 | 168.6 (4) | C19—C18—H18 | 111.2 |
C17—Pt1B—Cl10 | 86.8 (6) | C18—C19—H19A | 106.4 |
C17—Pt1B—Cl13 | 90.1 (6) | C18—C19—H19B | 106.4 |
C18—Pt1B—Cl10 | 86.4 (6) | C18—C19—C20 | 123.8 (13) |
C18—Pt1B—Cl13 | 97.6 (6) | H19A—C19—H19B | 106.4 |
C18—Pt1B—C17 | 36.9 (4) | C20—C19—H19A | 106.4 |
Pt1A—N2—H2AA | 109.5 | C20—C19—H19B | 106.4 |
Pt1A—N2—H2AB | 109.5 | C21—C20—C16 | 122.4 (6) |
Pt1B—N2—H2BC | 110.2 | C21—C20—C19 | 104.9 (8) |
Pt1B—N2—H2BD | 110.2 | C25—C20—C16 | 118.1 (6) |
H2AA—N2—H2AB | 108.1 | C25—C20—C19 | 133.4 (8) |
H2BC—N2—H2BD | 108.5 | C25—C20—C21 | 119.3 (5) |
C3—N2—Pt1A | 110.5 (3) | C20—C21—H21 | 119.8 |
C3—N2—Pt1B | 107.7 (3) | C22—C21—C20 | 120.4 (5) |
C3—N2—H2AA | 109.5 | C22—C21—H21 | 119.8 |
C3—N2—H2AB | 109.5 | C21—C22—C23 | 119.3 (5) |
C3—N2—H2BC | 110.2 | O26—C22—C21 | 124.6 (5) |
C3—N2—H2BD | 110.2 | O26—C22—C23 | 116.1 (4) |
C4—C3—N2 | 120.5 (5) | C24—C23—C22 | 119.7 (5) |
C4—C3—C8 | 119.5 (5) | O28—C23—C22 | 115.1 (5) |
C8—C3—N2 | 120.0 (5) | O28—C23—C24 | 125.2 (5) |
C3—C4—H4 | 119.6 | C23—C24—H24 | 119.7 |
C3—C4—C5 | 120.8 (6) | C23—C24—C25 | 120.6 (6) |
C5—C4—H4 | 119.6 | C25—C24—H24 | 119.7 |
C4—C5—H5 | 120.3 | C20—C25—C24 | 120.7 (6) |
C4—C5—C6 | 119.3 (6) | C20—C25—H25 | 119.7 |
C6—C5—H5 | 120.3 | C24—C25—H25 | 119.7 |
C5—C6—Cl9 | 119.9 (5) | C22—O26—C27 | 117.5 (4) |
C7—C6—C5 | 121.0 (6) | O26—C27—H27A | 109.5 |
C7—C6—Cl9 | 119.1 (4) | O26—C27—H27B | 109.5 |
C6—C7—H7 | 120.6 | O26—C27—H27C | 109.5 |
C6—C7—C8 | 118.9 (5) | H27A—C27—H27B | 109.5 |
C8—C7—H7 | 120.6 | H27A—C27—H27C | 109.5 |
C3—C8—C7 | 120.5 (5) | H27B—C27—H27C | 109.5 |
C3—C8—H8 | 119.7 | C23—O28—C29 | 115.7 (4) |
C7—C8—H8 | 119.7 | O28—C29—H29A | 110.4 |
Pt1A—C14—H14A | 112.4 | O28—C29—H29B | 110.4 |
Pt1A—C14—H14B | 84.2 | O28—C29—C30 | 106.8 (5) |
H14A—C14—H14B | 120.0 | H29A—C29—H29B | 108.6 |
C15—C14—Pt1A | 73.8 (4) | C30—C29—H29A | 110.4 |
C15—C14—H14A | 120.0 | C30—C29—H29B | 110.4 |
C15—C14—H14B | 120.0 | O31—C30—C29 | 125.9 (6) |
Pt1A—C15—H15 | 113.4 | O31—C30—O32 | 127.7 (6) |
C14—C15—Pt1A | 68.9 (5) | O32—C30—C29 | 105.7 (6) |
C14—C15—H15 | 113.4 | C30—O32—C33 | 115.0 (7) |
C14—C15—C16 | 124.8 (6) | O32—C33—H33A | 109.5 |
C16—C15—Pt1A | 115.3 (5) | O32—C33—H33B | 109.5 |
C16—C15—H15 | 113.4 | O32—C33—H33C | 109.5 |
C15—C16—H16A | 110.4 | H33A—C33—H33B | 109.5 |
C15—C16—H16B | 110.4 | H33A—C33—H33C | 109.5 |
C15—C16—C20 | 106.8 (5) | H33B—C33—H33C | 109.5 |
Pt1A—N2—C3—C4 | 85.5 (5) | C18—C19—C20—C21 | 170.4 (16) |
Pt1A—N2—C3—C8 | −92.9 (5) | C18—C19—C20—C25 | 9 (3) |
Pt1A—C14—C15—C16 | −106.8 (7) | C19—C20—C21—C22 | −165.6 (9) |
Pt1A—C15—C16—C20 | 83.1 (6) | C19—C20—C25—C24 | 161.9 (12) |
Pt1B—N2—C3—C4 | 76.9 (6) | C20—C21—C22—C23 | −1.4 (8) |
Pt1B—N2—C3—C8 | −101.5 (5) | C20—C21—C22—O26 | 177.9 (5) |
Pt1B—C17—C18—C19 | 109 (2) | C21—C20—C25—C24 | 2.1 (9) |
Pt1B—C18—C19—C20 | −65 (2) | C21—C22—C23—C24 | 1.9 (7) |
N2—C3—C4—C5 | −176.4 (5) | C21—C22—C23—O28 | 179.7 (4) |
N2—C3—C8—C7 | 177.4 (5) | C21—C22—O26—C27 | −2.8 (7) |
C3—C4—C5—C6 | −1.9 (10) | C22—C23—C24—C25 | −0.5 (8) |
C4—C3—C8—C7 | −1.0 (8) | C22—C23—O28—C29 | −179.6 (5) |
C4—C5—C6—C7 | 0.9 (9) | C23—C22—O26—C27 | 176.5 (4) |
C4—C5—C6—Cl9 | 179.6 (5) | C23—C24—C25—C20 | −1.6 (9) |
C5—C6—C7—C8 | 0.1 (8) | C23—O28—C29—C30 | 173.5 (4) |
C6—C7—C8—C3 | 0.0 (8) | C24—C23—O28—C29 | −2.0 (8) |
C8—C3—C4—C5 | 2.0 (9) | C25—C20—C21—C22 | −0.6 (8) |
Cl9—C6—C7—C8 | −178.7 (4) | O26—C22—C23—C24 | −177.4 (5) |
C14—C15—C16—C20 | 164.0 (7) | O26—C22—C23—O28 | 0.3 (6) |
C15—C16—C20—C21 | 80.3 (8) | O28—C23—C24—C25 | −178.0 (5) |
C15—C16—C20—C25 | −104.0 (7) | O28—C29—C30—O31 | −23.3 (9) |
C16—C20—C21—C22 | 175.0 (5) | O28—C29—C30—O32 | 165.6 (5) |
C16—C20—C25—C24 | −173.7 (6) | C29—C30—O32—C33 | −179.7 (6) |
C17—C18—C19—C20 | −153 (2) | O31—C30—O32—C33 | 9.4 (11) |
Cg1 is the centroid of the C20–C25 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2AA···O26i | 0.91 | 2.45 | 3.027 (5) | 122 |
N2—H2AA···O28i | 0.91 | 2.35 | 3.212 (6) | 158 |
N2—H2AB···O31ii | 0.91 | 2.41 | 3.302 (3) | 167 |
C16—H16A···Cl12 | 0.99 | 2.79 | 3.487 (10) | 128 |
C16—H16B···Cl9iii | 0.99 | 2.76 | 3.472 (8) | 129 |
C21—H21···Cl11iv | 0.95 | 2.82 | 3.726 (8) | 159 |
C29—H29B···Cl12v | 0.99 | 2.80 | 3.651 (7) | 145 |
C27—H27B···Cg1iv | 0.98 | 2.72 | 3.523 (6) | 139 |
Symmetry codes: (i) x+1/2, y−1/2, z; (ii) −x+3/2, y−1/2, −z+3/2; (iii) x−1/2, y−1/2, z; (iv) −x+1, y, −z+3/2; (v) −x+3/2, −y+3/2, −z+2. |
[PtCl2(C6H6ClN)(C14H18O4)] | Z = 2 |
Mr = 643.84 | F(000) = 624 |
Triclinic, P1 | Dx = 1.984 Mg m−3 |
a = 9.9093 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.0102 (3) Å | Cell parameters from 10730 reflections |
c = 11.1414 (4) Å | θ = 3.2–29.0° |
α = 97.302 (3)° | µ = 6.91 mm−1 |
β = 99.706 (3)° | T = 100 K |
γ = 92.572 (2)° | Block, yellow |
V = 1078.01 (6) Å3 | 0.3 × 0.3 × 0.15 mm |
Agilent SuperNova diffractometer (single source at offset, Eos detector) | 4378 independent reflections |
Radiation source: SuperNova (Mo) X-ray Source | 4177 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.044 |
Detector resolution: 15.9631 pixels mm-1 | θmax = 26.4°, θmin = 2.8° |
ω scans | h = −12→12 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) | k = −12→12 |
Tmin = 0.547, Tmax = 1.000 | l = −13→13 |
22329 measured reflections |
Refinement on F2 | Primary atom site location: iterative |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.026 | H-atom parameters constrained |
wR(F2) = 0.057 | w = 1/[σ2(Fo2) + (0.0056P)2 + 3.1214P] where P = (Fo2 + 2Fc2)/3 |
S = 1.20 | (Δ/σ)max < 0.001 |
4378 reflections | Δρmax = 0.97 e Å−3 |
292 parameters | Δρmin = −0.96 e Å−3 |
264 restraints |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Pt1A | 0.69549 (11) | 0.29586 (10) | 0.25083 (7) | 0.01218 (14) | 0.872 (6) |
Pt1B | 0.6572 (11) | 0.2618 (9) | 0.2299 (6) | 0.0263 (11) | 0.128 (6) |
N2 | 0.6352 (4) | 0.3773 (4) | 0.4142 (3) | 0.0175 (7) | |
H2AA | 0.6687 | 0.4649 | 0.4346 | 0.021* | 0.872 (6) |
H2AB | 0.5420 | 0.3754 | 0.4033 | 0.021* | 0.872 (6) |
H2BC | 0.6834 | 0.4588 | 0.4258 | 0.021* | 0.128 (6) |
H2BD | 0.5454 | 0.3921 | 0.4147 | 0.021* | 0.128 (6) |
C3 | 0.6861 (4) | 0.3007 (4) | 0.5131 (4) | 0.0172 (9) | |
C4 | 0.8223 (4) | 0.3217 (4) | 0.5704 (4) | 0.0191 (9) | |
H4 | 0.8815 | 0.3854 | 0.5446 | 0.023* | |
C5 | 0.8722 (4) | 0.2504 (4) | 0.6650 (4) | 0.0194 (9) | |
H5 | 0.9653 | 0.2646 | 0.7049 | 0.023* | |
C6 | 0.7836 (4) | 0.1577 (4) | 0.7002 (4) | 0.0182 (9) | |
C7 | 0.6483 (4) | 0.1340 (4) | 0.6433 (4) | 0.0191 (9) | |
H7 | 0.5897 | 0.0692 | 0.6685 | 0.023* | |
C8 | 0.5994 (4) | 0.2062 (4) | 0.5490 (4) | 0.0199 (9) | |
H8 | 0.5065 | 0.1912 | 0.5088 | 0.024* | |
Cl9 | 0.84620 (12) | 0.06618 (11) | 0.81957 (10) | 0.0252 (2) | |
Cl10 | 0.88980 (15) | 0.4404 (2) | 0.30141 (16) | 0.0170 (4) | 0.872 (6) |
Cl11 | 0.4916 (2) | 0.1647 (2) | 0.20164 (18) | 0.0173 (4) | 0.872 (6) |
Cl12 | 0.8689 (13) | 0.377 (2) | 0.2675 (13) | 0.037 (3) | 0.128 (6) |
Cl13 | 0.4387 (19) | 0.1586 (18) | 0.1984 (16) | 0.034 (3) | 0.128 (6) |
C14 | 0.7274 (5) | 0.2580 (5) | 0.0645 (4) | 0.0236 (10) | |
H14A | 0.6473 | 0.2280 | 0.0057 | 0.028* | |
H14B | 0.7579 | 0.3509 | 0.0794 | 0.028* | |
C15 | 0.8002 (5) | 0.1655 (5) | 0.1289 (4) | 0.0242 (10) | |
H15 | 0.9021 | 0.1839 | 0.1437 | 0.029* | 0.872 (6) |
H15A | 0.9000 | 0.1894 | 0.1608 | 0.029* | 0.128 (6) |
C16 | 0.7539 (5) | 0.0195 (4) | 0.1067 (4) | 0.0245 (10) | |
H16A | 0.8108 | −0.0272 | 0.0517 | 0.029* | |
H16B | 0.6582 | 0.0106 | 0.0616 | 0.029* | |
C17 | 0.7586 (5) | −0.0551 (4) | 0.2180 (4) | 0.0186 (9) | |
C18 | 0.6816 (4) | −0.1797 (4) | 0.1979 (4) | 0.0187 (9) | |
H18 | 0.6308 | −0.2117 | 0.1184 | 0.022* | |
C19 | 0.6787 (4) | −0.2565 (4) | 0.2923 (4) | 0.0161 (8) | |
C20 | 0.7528 (4) | −0.2097 (4) | 0.4101 (4) | 0.0143 (8) | |
C21 | 0.8282 (4) | −0.0865 (4) | 0.4312 (4) | 0.0174 (9) | |
H21 | 0.8780 | −0.0536 | 0.5108 | 0.021* | |
C22 | 0.8303 (4) | −0.0106 (4) | 0.3335 (4) | 0.0196 (9) | |
H22 | 0.8827 | 0.0736 | 0.3480 | 0.023* | |
O23 | 0.6053 (3) | −0.3770 (3) | 0.2818 (3) | 0.0183 (6) | |
C24 | 0.5250 (5) | −0.4260 (4) | 0.1644 (4) | 0.0241 (10) | |
H24A | 0.5845 | −0.4341 | 0.1023 | 0.036* | |
H24B | 0.4549 | −0.3629 | 0.1430 | 0.036* | |
H24C | 0.4805 | −0.5147 | 0.1672 | 0.036* | |
O25 | 0.7390 (3) | −0.2930 (3) | 0.4975 (3) | 0.0168 (6) | |
C26 | 0.8067 (4) | −0.2464 (4) | 0.6172 (4) | 0.0183 (9) | |
H26A | 0.7842 | −0.1526 | 0.6418 | 0.022* | |
H26B | 0.9072 | −0.2473 | 0.6214 | 0.022* | |
C27 | 0.7604 (4) | −0.3380 (4) | 0.7025 (4) | 0.0157 (8) | |
O28 | 0.6689 (3) | −0.4258 (3) | 0.6725 (3) | 0.0176 (6) | |
O29 | 0.8362 (3) | −0.3074 (3) | 0.8142 (3) | 0.0180 (6) | |
C30 | 0.8025 (5) | −0.3861 (5) | 0.9070 (4) | 0.0212 (10) | |
H30A | 0.8025 | −0.4837 | 0.8776 | 0.025* | |
H30B | 0.7103 | −0.3668 | 0.9249 | 0.025* | |
C31 | 0.9091 (4) | −0.3475 (4) | 1.0205 (4) | 0.0200 (9) | |
H31A | 0.9993 | −0.3714 | 1.0028 | 0.030* | |
H31B | 0.8865 | −0.3960 | 1.0864 | 0.030* | |
H31C | 0.9112 | −0.2501 | 1.0465 | 0.030* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Pt1A | 0.0123 (3) | 0.0118 (2) | 0.01192 (18) | −0.00266 (15) | 0.00058 (15) | 0.00299 (14) |
Pt1B | 0.030 (2) | 0.030 (2) | 0.0207 (16) | −0.0011 (19) | 0.0073 (16) | 0.0081 (15) |
N2 | 0.0171 (17) | 0.0194 (18) | 0.0155 (19) | −0.0007 (14) | 0.0029 (14) | 0.0010 (14) |
C3 | 0.020 (2) | 0.017 (2) | 0.015 (2) | 0.0008 (16) | 0.0050 (16) | 0.0017 (16) |
C4 | 0.021 (2) | 0.020 (2) | 0.016 (2) | −0.0049 (17) | 0.0044 (17) | 0.0020 (17) |
C5 | 0.018 (2) | 0.024 (2) | 0.015 (2) | −0.0034 (17) | 0.0022 (17) | 0.0002 (18) |
C6 | 0.025 (2) | 0.018 (2) | 0.012 (2) | 0.0003 (16) | 0.0033 (17) | 0.0014 (17) |
C7 | 0.022 (2) | 0.017 (2) | 0.019 (2) | −0.0041 (16) | 0.0076 (17) | 0.0024 (17) |
C8 | 0.0146 (19) | 0.026 (2) | 0.019 (2) | −0.0033 (17) | 0.0030 (17) | 0.0048 (18) |
Cl9 | 0.0379 (6) | 0.0240 (6) | 0.0123 (6) | −0.0029 (5) | 0.0008 (5) | 0.0041 (4) |
Cl10 | 0.0148 (6) | 0.0174 (8) | 0.0176 (8) | −0.0065 (5) | 0.0010 (5) | 0.0032 (6) |
Cl11 | 0.0124 (8) | 0.0174 (7) | 0.0201 (8) | −0.0054 (7) | 0.0009 (7) | −0.0005 (5) |
Cl12 | 0.034 (5) | 0.049 (8) | 0.026 (6) | −0.013 (5) | 0.010 (4) | 0.003 (5) |
Cl13 | 0.033 (7) | 0.036 (6) | 0.034 (7) | −0.002 (6) | 0.011 (6) | 0.002 (5) |
C14 | 0.030 (2) | 0.025 (2) | 0.017 (2) | 0.0025 (19) | 0.0043 (18) | 0.0060 (18) |
C15 | 0.028 (2) | 0.025 (2) | 0.022 (2) | −0.0012 (18) | 0.0084 (19) | 0.0056 (18) |
C16 | 0.040 (3) | 0.020 (2) | 0.014 (2) | −0.0026 (19) | 0.008 (2) | 0.0022 (17) |
C17 | 0.031 (2) | 0.0151 (19) | 0.012 (2) | 0.0047 (17) | 0.0083 (17) | 0.0035 (16) |
C18 | 0.027 (2) | 0.018 (2) | 0.011 (2) | 0.0009 (17) | 0.0024 (17) | 0.0029 (16) |
C19 | 0.018 (2) | 0.0155 (19) | 0.015 (2) | 0.0009 (15) | 0.0048 (16) | 0.0033 (15) |
C20 | 0.0158 (19) | 0.0154 (19) | 0.013 (2) | 0.0009 (15) | 0.0025 (15) | 0.0052 (15) |
C21 | 0.019 (2) | 0.019 (2) | 0.013 (2) | −0.0031 (16) | 0.0016 (16) | 0.0022 (16) |
C22 | 0.024 (2) | 0.015 (2) | 0.020 (2) | −0.0035 (17) | 0.0058 (17) | 0.0041 (17) |
O23 | 0.0226 (15) | 0.0182 (15) | 0.0127 (16) | −0.0043 (12) | −0.0018 (12) | 0.0046 (12) |
C24 | 0.034 (3) | 0.020 (2) | 0.016 (2) | −0.0050 (19) | −0.0040 (19) | 0.0067 (18) |
O25 | 0.0236 (15) | 0.0160 (14) | 0.0098 (15) | −0.0047 (12) | −0.0009 (12) | 0.0054 (12) |
C26 | 0.019 (2) | 0.019 (2) | 0.015 (2) | −0.0050 (17) | −0.0003 (16) | 0.0048 (17) |
C27 | 0.0174 (19) | 0.016 (2) | 0.014 (2) | 0.0026 (16) | 0.0029 (15) | 0.0020 (16) |
O28 | 0.0221 (15) | 0.0177 (15) | 0.0112 (16) | −0.0046 (12) | 0.0005 (12) | 0.0009 (12) |
O29 | 0.0186 (15) | 0.0225 (16) | 0.0123 (15) | −0.0057 (12) | −0.0003 (12) | 0.0063 (12) |
C30 | 0.027 (2) | 0.024 (2) | 0.013 (2) | −0.0056 (18) | 0.0030 (18) | 0.0045 (18) |
C31 | 0.025 (2) | 0.023 (2) | 0.012 (2) | −0.0006 (18) | 0.0004 (17) | 0.0040 (18) |
Pt1A—N2 | 2.089 (4) | C16—H16A | 0.9900 |
Pt1A—Cl10 | 2.3011 (14) | C16—H16B | 0.9900 |
Pt1A—Cl11 | 2.3050 (15) | C16—C17 | 1.522 (6) |
Pt1A—C14 | 2.142 (5) | C17—C18 | 1.406 (6) |
Pt1A—C15 | 2.184 (5) | C17—C22 | 1.371 (6) |
Pt1B—N2 | 2.273 (8) | C18—H18 | 0.9500 |
Pt1B—Cl12 | 2.297 (12) | C18—C19 | 1.382 (6) |
Pt1B—Cl13 | 2.309 (14) | C19—C20 | 1.403 (6) |
Pt1B—C14 | 2.073 (6) | C19—O23 | 1.362 (5) |
Pt1B—C15 | 2.142 (6) | C20—C21 | 1.385 (6) |
N2—H2AA | 0.9100 | C20—O25 | 1.380 (5) |
N2—H2AB | 0.9100 | C21—H21 | 0.9500 |
N2—H2BC | 0.9100 | C21—C22 | 1.406 (6) |
N2—H2BD | 0.9100 | C22—H22 | 0.9500 |
N2—C3 | 1.455 (5) | O23—C24 | 1.427 (5) |
C3—C4 | 1.387 (6) | C24—H24A | 0.9800 |
C3—C8 | 1.390 (6) | C24—H24B | 0.9800 |
C4—H4 | 0.9500 | C24—H24C | 0.9800 |
C4—C5 | 1.383 (6) | O25—C26 | 1.399 (5) |
C5—H5 | 0.9500 | C26—H26A | 0.9900 |
C5—C6 | 1.387 (6) | C26—H26B | 0.9900 |
C6—C7 | 1.379 (6) | C26—C27 | 1.512 (5) |
C6—Cl9 | 1.754 (4) | C27—O28 | 1.207 (5) |
C7—H7 | 0.9500 | C27—O29 | 1.332 (5) |
C7—C8 | 1.384 (6) | O29—C30 | 1.449 (5) |
C8—H8 | 0.9500 | C30—H30A | 0.9900 |
C14—H14A | 0.9500 | C30—H30B | 0.9900 |
C14—H14B | 0.9500 | C30—C31 | 1.501 (6) |
C14—C15 | 1.396 (6) | C31—H31A | 0.9800 |
C15—H15 | 1.0000 | C31—H31B | 0.9800 |
C15—H15A | 1.0000 | C31—H31C | 0.9800 |
C15—C16 | 1.489 (6) | ||
N2—Pt1A—Cl10 | 88.86 (10) | C14—C15—H15 | 114.2 |
N2—Pt1A—Cl11 | 88.77 (11) | C14—C15—H15A | 117.2 |
N2—Pt1A—C14 | 163.99 (15) | C14—C15—C16 | 120.7 (4) |
N2—Pt1A—C15 | 158.31 (16) | C16—C15—Pt1A | 116.5 (3) |
Cl10—Pt1A—Cl11 | 175.82 (7) | C16—C15—Pt1B | 105.3 (4) |
C14—Pt1A—Cl10 | 90.53 (14) | C16—C15—H15 | 114.2 |
C14—Pt1A—Cl11 | 90.80 (15) | C16—C15—H15A | 117.2 |
C14—Pt1A—C15 | 37.62 (17) | C15—C16—H16A | 107.9 |
C15—Pt1A—Cl10 | 89.13 (14) | C15—C16—H16B | 107.9 |
C15—Pt1A—Cl11 | 94.33 (15) | C15—C16—C17 | 117.8 (4) |
N2—Pt1B—Cl12 | 83.8 (4) | H16A—C16—H16B | 107.2 |
N2—Pt1B—Cl13 | 93.1 (5) | C17—C16—H16A | 107.9 |
Cl12—Pt1B—Cl13 | 176.1 (6) | C17—C16—H16B | 107.9 |
C14—Pt1B—N2 | 149.1 (6) | C18—C17—C16 | 115.9 (4) |
C14—Pt1B—Cl12 | 71.8 (5) | C22—C17—C16 | 125.5 (4) |
C14—Pt1B—Cl13 | 110.3 (7) | C22—C17—C18 | 118.6 (4) |
C14—Pt1B—C15 | 38.62 (18) | C17—C18—H18 | 119.6 |
C15—Pt1B—N2 | 143.8 (6) | C19—C18—C17 | 120.8 (4) |
C15—Pt1B—Cl12 | 67.1 (6) | C19—C18—H18 | 119.6 |
C15—Pt1B—Cl13 | 116.7 (7) | C18—C19—C20 | 119.9 (4) |
Pt1A—N2—H2AA | 109.6 | O23—C19—C18 | 124.8 (4) |
Pt1A—N2—H2AB | 109.6 | O23—C19—C20 | 115.2 (3) |
Pt1B—N2—H2BC | 109.6 | C21—C20—C19 | 119.7 (4) |
Pt1B—N2—H2BD | 109.6 | O25—C20—C19 | 114.7 (3) |
H2AA—N2—H2AB | 108.1 | O25—C20—C21 | 125.6 (4) |
H2BC—N2—H2BD | 108.2 | C20—C21—H21 | 120.3 |
C3—N2—Pt1A | 110.4 (3) | C20—C21—C22 | 119.4 (4) |
C3—N2—Pt1B | 110.1 (3) | C22—C21—H21 | 120.3 |
C3—N2—H2AA | 109.6 | C17—C22—C21 | 121.5 (4) |
C3—N2—H2AB | 109.6 | C17—C22—H22 | 119.2 |
C3—N2—H2BC | 109.6 | C21—C22—H22 | 119.2 |
C3—N2—H2BD | 109.6 | C19—O23—C24 | 117.0 (3) |
C4—C3—N2 | 119.5 (4) | O23—C24—H24A | 109.5 |
C4—C3—C8 | 120.2 (4) | O23—C24—H24B | 109.5 |
C8—C3—N2 | 120.4 (4) | O23—C24—H24C | 109.5 |
C3—C4—H4 | 119.9 | H24A—C24—H24B | 109.5 |
C5—C4—C3 | 120.3 (4) | H24A—C24—H24C | 109.5 |
C5—C4—H4 | 119.9 | H24B—C24—H24C | 109.5 |
C4—C5—H5 | 120.7 | C20—O25—C26 | 116.1 (3) |
C4—C5—C6 | 118.6 (4) | O25—C26—H26A | 110.0 |
C6—C5—H5 | 120.7 | O25—C26—H26B | 110.0 |
C5—C6—Cl9 | 118.9 (3) | O25—C26—C27 | 108.3 (3) |
C7—C6—C5 | 122.1 (4) | H26A—C26—H26B | 108.4 |
C7—C6—Cl9 | 119.0 (3) | C27—C26—H26A | 110.0 |
C6—C7—H7 | 120.6 | C27—C26—H26B | 110.0 |
C6—C7—C8 | 118.7 (4) | O28—C27—C26 | 124.6 (4) |
C8—C7—H7 | 120.6 | O28—C27—O29 | 125.8 (4) |
C3—C8—H8 | 119.9 | O29—C27—C26 | 109.7 (3) |
C7—C8—C3 | 120.1 (4) | C27—O29—C30 | 116.1 (3) |
C7—C8—H8 | 119.9 | O29—C30—H30A | 110.2 |
Pt1A—C14—H14A | 115.0 | O29—C30—H30B | 110.2 |
Pt1A—C14—H14B | 82.6 | O29—C30—C31 | 107.6 (3) |
H14A—C14—H14B | 120.0 | H30A—C30—H30B | 108.5 |
C15—C14—Pt1A | 72.9 (3) | C31—C30—H30A | 110.2 |
C15—C14—Pt1B | 73.4 (3) | C31—C30—H30B | 110.2 |
C15—C14—H14A | 120.0 | C30—C31—H31A | 109.5 |
C15—C14—H14B | 120.0 | C30—C31—H31B | 109.5 |
Pt1A—C15—H15 | 114.2 | C30—C31—H31C | 109.5 |
Pt1B—C15—H15A | 117.2 | H31A—C31—H31B | 109.5 |
C14—C15—Pt1A | 69.5 (3) | H31A—C31—H31C | 109.5 |
C14—C15—Pt1B | 68.0 (3) | H31B—C31—H31C | 109.5 |
Pt1A—N2—C3—C4 | 78.3 (4) | C16—C17—C22—C21 | 179.8 (4) |
Pt1A—N2—C3—C8 | −101.0 (4) | C17—C18—C19—C20 | 0.3 (6) |
Pt1A—C14—C15—C16 | 109.4 (4) | C17—C18—C19—O23 | 178.8 (4) |
Pt1A—C15—C16—C17 | −56.7 (5) | C18—C17—C22—C21 | 0.0 (7) |
Pt1B—N2—C3—C4 | 91.5 (5) | C18—C19—C20—C21 | 0.2 (6) |
Pt1B—N2—C3—C8 | −87.8 (5) | C18—C19—C20—O25 | 178.3 (4) |
Pt1B—C14—C15—C16 | 95.3 (6) | C18—C19—O23—C24 | −0.5 (6) |
Pt1B—C15—C16—C17 | −64.4 (5) | C19—C20—C21—C22 | −0.6 (6) |
N2—C3—C4—C5 | 179.7 (4) | C19—C20—O25—C26 | −177.2 (3) |
N2—C3—C8—C7 | −179.8 (4) | C20—C19—O23—C24 | 178.1 (4) |
C3—C4—C5—C6 | 0.3 (7) | C20—C21—C22—C17 | 0.5 (7) |
C4—C3—C8—C7 | 0.9 (7) | C20—O25—C26—C27 | 170.4 (3) |
C4—C5—C6—C7 | 0.6 (7) | C21—C20—O25—C26 | 0.7 (6) |
C4—C5—C6—Cl9 | 179.7 (3) | C22—C17—C18—C19 | −0.4 (6) |
C5—C6—C7—C8 | −0.7 (7) | O23—C19—C20—C21 | −178.5 (4) |
C6—C7—C8—C3 | 0.0 (7) | O23—C19—C20—O25 | −0.4 (5) |
C8—C3—C4—C5 | −1.0 (7) | O25—C20—C21—C22 | −178.4 (4) |
Cl9—C6—C7—C8 | −179.8 (3) | O25—C26—C27—O28 | −7.9 (6) |
C14—C15—C16—C17 | −137.6 (5) | O25—C26—C27—O29 | 171.8 (3) |
C15—C16—C17—C18 | 163.5 (4) | C26—C27—O29—C30 | 179.3 (3) |
C15—C16—C17—C22 | −16.3 (7) | C27—O29—C30—C31 | 173.4 (4) |
C16—C17—C18—C19 | 179.8 (4) | O28—C27—O29—C30 | −1.1 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2AA···O23i | 0.91 | 2.49 | 3.025 (5) | 118 |
N2—H2AA···O25i | 0.91 | 2.47 | 3.377 (5) | 174 |
N2—H2AB···O28ii | 0.91 | 2.22 | 3.085 (5) | 158 |
C26—H26A···Cl9 | 0.99 | 2.73 | 3.581 (4) | 144 |
Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y, −z+1. |
Acknowledgements
The authors thank VLIR–UOS (project ZEIN2014Z182) for financial support and the Hercules Foundation for supporting the purchase of the diffractometer through project AKUL/09/0035.
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