Mixed natural aryl­olefin–quinoline platinum(II) complexes: synthesis, structural characterization and in vitro cytotoxicity studies

Chi, N.T.T.; Thong, P.V.; Mai, T.T.C.; Van Meervelt, L.

doi:10.1107/S2053229618015978

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Mixed natural arylolefin–quinoline platinum(II) complexes: synthesis, structural characterization and in vitro cytotoxicity studies

N. T. T. Chi, P. V. Thong, T. T. C. Mai and L. Van Meervelt

Five new platinum(II) complexes bearing a eugenol and a quinoline derivative, namely [η²-4-allyl-2-methoxy-1-(propoxycarbonylmethoxy)benzene]-trans-dichlorido(quinoline-κN)platinum(II), [PtCl₂(C₁₅H₂₀O₄)(C₉H₇N)], (2), {η²-4-allyl-2-methoxy-1-[(propan-2-yloxy)carbonylmethoxy]benzene}-trans-dichlorido(quinoline-κN)platinum(II), [PtCl₂(C₁₅H₁₉O₄)(C₉H₇N)], (3), [η²-4-allyl-2-methoxy-1-(propoxycarbonylmethoxy)benzene]chlorido(quinolin-8-olato-κ²N,O)platinum(II), [Pt(C₉H₆NO)Cl(C₁₅H₂₀O₄)], (4), {η²-4-allyl-2-methoxy-1-[(propan-2-yloxy)carbonylmethoxy]benzene}chlorido(quinolin-8-olato-κ²N,O)platinum(II), [Pt(C₉H₆NO)Cl(C₁₅H₂₀O₄)], (5), and [η²-4-allyl-2-methoxy-1-(propoxycarbonylmethoxy)benzene]chlorido(quinolin-2-carboxylato-κ²N,O)platinum(II), [Pt(C₁₀H₆NO₂)Cl(C₁₅H₂₀O₄)], (6), have been synthesized and fully characterized spectroscopically. A single-crystal X-ray diffraction study was carried out for complexes (2) and (4)–(6). PrEug [or 4-allyl-2-methoxy-1-(propoxycarbonylmethoxy)benzene] in (2), (4) and (6), and ⁱPrEug (the propan-2-yloxy analogue of PrEug) in (3) and (5) coordinate with Pt^II at the ethylenic double bond of the allyl group. In (2)–(6), the donor N atom of the amine group occupies a trans position with respect to the double bond. A comparison of the IC₅₀ values of 0.38–29.23 µM for (2)–(6) with cisplatin, as well as other platinum(II) complexes, indicates an excellent in vitro cytotoxicity against the KB, LU, Hep-G2 and MCF-7 cancer cell lines, with the highest cytotoxic effect (IC₅₀ = 0.38–1.99 µM) being for complexes (4) and (5) bearing a quinolin-8-olate ligand.

Keywords: platinum(II) complexes; crystal structure; anticancer activity; eugenol derivatives; quinoline.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229618015978/ly3081sup1.cif Contains datablocks chi29, chi30, chi9, chi33, global
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229618015978/ly3081chi30sup2.hkl Contains datablock chi30
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229618015978/ly3081chi9sup3.hkl Contains datablock chi9
	Portable Document Format (PDF) file https://doi.org/10.1107/S2053229618015978/ly3081sup4.pdf ESI-MS and NMR spectra

CCDC references: 1878366; 1878365; 1878364; 1878363

Computing details top

For all structures, data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

[η²-4-Allyl-2-methoxy-1-(propoxycarbonylmethoxy)benzene]-trans-dichlorido(quinoline-κN)platinum(II) (chi29) top

Crystal data top

[PtCl₂(C₁₅H₂₀O₄)(C₉H₇N)]	Z = 2
M_r = 659.45	F(000) = 644
Triclinic, P1	D_x = 1.845 Mg m⁻³
a = 8.1252 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.7042 (4) Å	Cell parameters from 9524 reflections
c = 13.7340 (5) Å	θ = 3.1–28.7°
α = 65.864 (4)°	µ = 6.17 mm⁻¹
β = 84.716 (3)°	T = 100 K
γ = 88.191 (3)°	Needle, yellow
V = 1186.82 (9) Å³	0.35 × 0.1 × 0.1 mm

Data collection top

Agilent SuperNova Dual Source diffractometer with an Eos detector	4867 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	4458 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.036
Detector resolution: 15.9631 pixels mm^-1	θ_max = 26.4°, θ_min = 2.9°
ω scans	h = −10→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	k = −14→14
T_min = 0.432, T_max = 1.000	l = −16→17
19752 measured reflections

Refinement top

Refinement on F²	14 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.036	H-atom parameters constrained
wR(F²) = 0.073	w = 1/[σ²(F_o²) + (0.0079P)² + 5.6087P] where P = (F_o² + 2F_c²)/3
S = 1.12	(Δ/σ)_max < 0.001
4867 reflections	Δρ_max = 3.21 e Å⁻³
337 parameters	Δρ_min = −1.79 e Å⁻³

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Pt1A	0.7798 (3)	1.14396 (15)	0.16089 (7)	0.0218 (2)	0.656 (8)
Pt1B	0.8263 (6)	1.1211 (3)	0.15616 (15)	0.0265 (4)	0.344 (8)
Cl2A	0.5445 (3)	1.2493 (3)	0.1821 (2)	0.0266 (6)	0.656 (8)
Cl2B	0.5661 (6)	1.1993 (8)	0.1688 (4)	0.0363 (13)	0.344 (8)
Cl3A	1.0244 (5)	1.0451 (3)	0.1445 (2)	0.0277 (6)	0.656 (8)
Cl3B	1.0943 (11)	1.0535 (7)	0.1458 (5)	0.0387 (15)	0.344 (8)
N4	0.8817 (5)	1.1787 (4)	0.2779 (3)	0.0304 (9)
C5	0.9845 (6)	1.2744 (4)	0.2488 (4)	0.0270 (10)
H5	1.017631	1.317137	0.174624	0.032*
C6	1.0480 (6)	1.3173 (5)	0.3183 (4)	0.0291 (11)
H6	1.121358	1.387069	0.292850	0.035*
C7	0.9996 (6)	1.2538 (5)	0.4266 (4)	0.0331 (12)
H7	1.038101	1.280591	0.477129	0.040*
C8	0.8923 (5)	1.1485 (4)	0.4616 (4)	0.0220 (9)
C9	0.8457 (6)	1.0762 (5)	0.5707 (4)	0.0329 (12)
H9	0.886544	1.098149	0.623483	0.039*
C10	0.7439 (6)	0.9763 (5)	0.6016 (4)	0.0360 (12)
H10	0.711827	0.929103	0.675353	0.043*
C11	0.6863 (6)	0.9429 (5)	0.5240 (4)	0.0292 (11)
H11	0.614478	0.872448	0.546956	0.035*
C12	0.7277 (5)	1.0061 (4)	0.4171 (4)	0.0263 (10)
H12	0.687704	0.980387	0.366333	0.032*
C13	0.8345 (6)	1.1133 (5)	0.3841 (4)	0.0266 (10)
C14A	0.7271 (13)	1.1640 (9)	0.0050 (8)	0.027 (2)	0.656 (8)
H14A	0.818330	1.150443	−0.037382	0.033*	0.656 (8)
H14B	0.699529	1.246656	−0.002897	0.033*	0.656 (8)
C14B	0.783 (3)	1.1440 (12)	−0.0069 (16)	0.025 (5)	0.344 (8)
H14C	0.682405	1.183980	−0.033108	0.030*	0.344 (8)
H14D	0.883222	1.190307	−0.027753	0.030*	0.344 (8)
C15A	0.6335 (8)	1.0627 (6)	0.0787 (5)	0.0219 (17)	0.656 (8)
H15A	0.514099	1.084817	0.083641	0.026*	0.656 (8)
C15B	0.7818 (15)	1.0182 (12)	0.0618 (10)	0.030 (4)	0.344 (8)
H15B	0.885328	0.976909	0.047701	0.036*	0.344 (8)
C16	0.6538 (8)	0.9333 (5)	0.1026 (4)	0.0433 (15)
H16A	0.764296	0.922215	0.070763	0.052*	0.656 (8)
H16B	0.571023	0.909066	0.065743	0.052*	0.656 (8)
H16C	0.658121	0.882998	0.059340	0.052*	0.344 (8)
H16D	0.549857	0.981538	0.089099	0.052*	0.344 (8)
C17	0.6386 (7)	0.8423 (5)	0.2189 (4)	0.0303 (11)
C18	0.7735 (6)	0.7702 (4)	0.2630 (4)	0.0263 (10)
H18	0.873913	0.778617	0.219332	0.032*
C19	0.7647 (6)	0.6864 (4)	0.3692 (4)	0.0247 (10)
C20	0.6174 (6)	0.6750 (4)	0.4348 (4)	0.0259 (10)
C21	0.4818 (6)	0.7449 (5)	0.3906 (4)	0.0306 (11)
H21	0.380501	0.735833	0.433631	0.037*
C22	0.4930 (7)	0.8286 (5)	0.2830 (4)	0.0347 (12)
H22	0.399386	0.876730	0.253642	0.042*
O23	0.8917 (4)	0.6111 (3)	0.4178 (3)	0.0280 (7)
C24	1.0443 (6)	0.6212 (5)	0.3527 (4)	0.0331 (12)
H24A	1.024473	0.600999	0.292203	0.050*
H24B	1.124805	0.562539	0.395878	0.050*
H24C	1.087552	0.706805	0.325834	0.050*
O25	0.6212 (4)	0.5923 (3)	0.5400 (3)	0.0294 (8)
C26	0.4797 (6)	0.5859 (5)	0.6092 (4)	0.0271 (10)
H26A	0.385482	0.550928	0.589158	0.032*
H26B	0.449664	0.670725	0.604002	0.032*
C27	0.5177 (6)	0.5029 (4)	0.7221 (4)	0.0269 (10)
O28	0.6508 (4)	0.4610 (3)	0.7501 (3)	0.0340 (8)
O29	0.3804 (4)	0.4862 (3)	0.7874 (3)	0.0296 (8)
C30	0.3997 (6)	0.4167 (5)	0.9005 (4)	0.0313 (11)
H30A	0.497099	0.447884	0.920848	0.038*
H30B	0.415443	0.326622	0.917035	0.038*
C31	0.2440 (6)	0.4356 (5)	0.9611 (4)	0.0334 (12)
H31A	0.229895	0.526173	0.943080	0.040*
H31B	0.255733	0.392959	1.038969	0.040*
C32	0.0907 (6)	0.3855 (5)	0.9357 (4)	0.0331 (12)
H32A	0.076437	0.429307	0.859105	0.050*
H32B	−0.006417	0.399117	0.977384	0.050*
H32C	0.103443	0.295626	0.954158	0.050*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pt1A	0.0224 (5)	0.0218 (4)	0.02258 (19)	0.0050 (3)	−0.0097 (2)	−0.00915 (19)
Pt1B	0.0303 (10)	0.0276 (6)	0.0235 (4)	0.0092 (6)	−0.0126 (5)	−0.0109 (4)
Cl2A	0.0234 (10)	0.0243 (13)	0.0346 (11)	0.0062 (9)	−0.0088 (8)	−0.0136 (10)
Cl2B	0.034 (2)	0.040 (3)	0.035 (2)	0.010 (2)	−0.0070 (17)	−0.015 (2)
Cl3A	0.0237 (15)	0.0344 (12)	0.0284 (11)	0.0061 (13)	−0.0057 (12)	−0.0161 (9)
Cl3B	0.034 (4)	0.053 (3)	0.036 (2)	0.012 (3)	−0.010 (3)	−0.024 (2)
N4	0.027 (2)	0.033 (2)	0.031 (2)	0.0013 (18)	−0.0066 (18)	−0.0131 (19)
C5	0.025 (2)	0.025 (3)	0.028 (2)	−0.004 (2)	−0.001 (2)	−0.008 (2)
C6	0.027 (3)	0.026 (3)	0.038 (3)	0.003 (2)	−0.008 (2)	−0.016 (2)
C7	0.028 (3)	0.036 (3)	0.044 (3)	0.009 (2)	−0.009 (2)	−0.024 (3)
C8	0.016 (2)	0.026 (2)	0.026 (2)	0.0102 (18)	−0.0037 (18)	−0.014 (2)
C9	0.030 (3)	0.038 (3)	0.026 (3)	0.014 (2)	0.000 (2)	−0.011 (2)
C10	0.031 (3)	0.038 (3)	0.032 (3)	0.013 (2)	0.003 (2)	−0.009 (2)
C11	0.019 (2)	0.027 (3)	0.036 (3)	0.006 (2)	−0.002 (2)	−0.008 (2)
C12	0.019 (2)	0.027 (3)	0.029 (2)	0.0057 (19)	−0.0062 (19)	−0.007 (2)
C13	0.021 (2)	0.031 (3)	0.027 (2)	0.013 (2)	−0.0087 (19)	−0.010 (2)
C14A	0.035 (6)	0.035 (5)	0.015 (4)	−0.001 (4)	0.000 (4)	−0.013 (4)
C14B	0.028 (8)	0.032 (8)	0.013 (7)	−0.010 (6)	0.001 (6)	−0.007 (6)
C15A	0.022 (4)	0.024 (4)	0.022 (3)	0.000 (3)	−0.011 (3)	−0.009 (3)
C15B	0.035 (7)	0.038 (7)	0.022 (6)	0.003 (5)	−0.008 (5)	−0.017 (5)
C16	0.078 (4)	0.025 (3)	0.027 (3)	−0.005 (3)	−0.020 (3)	−0.006 (2)
C17	0.043 (3)	0.021 (3)	0.028 (3)	−0.003 (2)	−0.011 (2)	−0.008 (2)
C18	0.033 (3)	0.021 (2)	0.024 (2)	0.000 (2)	−0.002 (2)	−0.010 (2)
C19	0.027 (2)	0.021 (2)	0.027 (2)	0.0047 (19)	−0.0043 (19)	−0.010 (2)
C20	0.023 (2)	0.021 (2)	0.030 (3)	0.0009 (19)	0.0007 (19)	−0.008 (2)
C21	0.024 (2)	0.023 (3)	0.041 (3)	0.004 (2)	−0.003 (2)	−0.009 (2)
C22	0.035 (3)	0.026 (3)	0.045 (3)	0.008 (2)	−0.017 (2)	−0.014 (2)
O23	0.0241 (17)	0.0315 (19)	0.0235 (17)	0.0103 (14)	0.0027 (13)	−0.0079 (15)
C24	0.026 (3)	0.040 (3)	0.028 (3)	0.006 (2)	0.006 (2)	−0.011 (2)
O25	0.0275 (18)	0.0244 (18)	0.0228 (17)	0.0054 (14)	0.0111 (14)	0.0009 (14)
C26	0.019 (2)	0.024 (3)	0.034 (3)	0.0021 (19)	0.0087 (19)	−0.010 (2)
C27	0.027 (3)	0.019 (2)	0.033 (3)	−0.004 (2)	0.007 (2)	−0.010 (2)
O28	0.0217 (18)	0.036 (2)	0.035 (2)	0.0053 (15)	0.0056 (15)	−0.0076 (16)
O29	0.0236 (17)	0.037 (2)	0.0259 (17)	0.0019 (15)	0.0049 (14)	−0.0126 (15)
C30	0.024 (2)	0.037 (3)	0.029 (3)	0.005 (2)	0.001 (2)	−0.011 (2)
C31	0.025 (3)	0.044 (3)	0.030 (3)	0.001 (2)	0.006 (2)	−0.015 (2)
C32	0.031 (3)	0.034 (3)	0.032 (3)	0.001 (2)	0.005 (2)	−0.013 (2)

Geometric parameters (Å, º) top

PT1Aa—Cl2A	2.303 (2)	C12—C13	1.437 (7)
PT1Bb—Cl2B	2.298 (5)	C16—H16A	0.9900
PT1Aa—Cl3A	2.307 (3)	C16—H16B	0.9900
PT1Bb—Cl3B	2.305 (6)	C16—H16C	0.9900
PT1Aa—N4	2.058 (4)	C16—H16D	0.9900
PT1Bb—N4	2.129 (5)	C16—C17	1.510 (7)
PT1Aa—C14A	2.139 (11)	C17—C18	1.388 (7)
C14Aa—H14A	0.9500	C17—C22	1.381 (8)
C14Aa—H14B	0.9500	C18—H18	0.9500
PT1Bb—C14B	2.20 (2)	C18—C19	1.382 (6)
C14Bb—H14C	0.9500	C19—C20	1.406 (7)
C14Bb—H14D	0.9500	C19—O23	1.369 (5)
C14Aa—C15A	1.394 (9)	C20—C21	1.382 (7)
PT1Aa—C15A	2.188 (6)	C20—O25	1.374 (6)
C15Aa—H15A	1.0000	C21—H21	0.9500
PT1Bb—C15B	2.157 (13)	C21—C22	1.396 (7)
C14Bb—C15B	1.386 (11)	C22—H22	0.9500
C15Bb—H15B	1.0000	O23—C24	1.438 (5)
C15Bb—C16	1.373 (10)	C24—H24A	0.9800
C15Aa—C16	1.420 (8)	C24—H24B	0.9800
N4—C5	1.320 (6)	C24—H24C	0.9800
N4—C13	1.365 (6)	O25—C26	1.406 (5)
C5—H5	0.9500	C26—H26A	0.9900
C5—C6	1.389 (7)	C26—H26B	0.9900
C6—H6	0.9500	C26—C27	1.510 (7)
C6—C7	1.388 (7)	C27—O28	1.203 (6)
C7—H7	0.9500	C27—O29	1.332 (6)
C7—C8	1.419 (7)	O29—C30	1.450 (6)
C8—C9	1.409 (7)	C30—H30A	0.9900
C8—C13	1.408 (6)	C30—H30B	0.9900
C9—H9	0.9500	C30—C31	1.511 (6)
C9—C10	1.350 (8)	C31—H31A	0.9900
C10—H10	0.9500	C31—H31B	0.9900
C10—C11	1.398 (7)	C31—C32	1.521 (7)
C11—H11	0.9500	C32—H32A	0.9800
C11—C12	1.361 (7)	C32—H32B	0.9800
C12—H12	0.9500	C32—H32C	0.9800

C14Aa—C15Aa—Pt1A	69.3 (6)	C15Bb—C16—H16D	107.1
C15Aa—C14Aa—Pt1A	73.1 (5)	H16Cb—C16—H16D	106.8
C5—N4—Pt1A	118.8 (3)	C15Aa—C16—C17	117.9 (5)
C5—N4—Pt1B	116.7 (3)	C15Bb—C16—C17	121.0 (7)
C5—N4—C13	119.0 (4)	C18—C17—C16	119.7 (5)
C13—N4—Pt1A	121.9 (3)	C22—C17—C16	121.6 (5)
C13—N4—Pt1B	123.7 (3)	C22—C17—C18	118.7 (5)
N4—C5—H5	117.5	C17—C18—H18	119.3
C14Bb—C15Bb—Pt1B	73.4 (11)	C19—C18—C17	121.4 (5)
C15Bb—C14Bb—Pt1B	69.6 (10)	C19—C18—H18	119.3
C15Aa—PT1Aa—Cl2A	87.0 (2)	C18—C19—C20	119.6 (4)
C14Aa—PT1Aa—Cl2A	92.7 (3)	O23—C19—C18	124.7 (4)
C15Bb—PT1Bb—Cl2B	99.5 (5)	O23—C19—C20	115.8 (4)
C14Bb—PT1Bb—Cl2B	87.8 (5)	C21—C20—C19	119.2 (4)
C15Aa—PT1Aa—Cl3A	96.6 (2)	O25—C20—C19	115.7 (4)
CL2Aa—PT1Aa—Cl3A	176.37 (10)	O25—C20—C21	125.1 (4)
C14Aa—PT1Aa—Cl3A	90.0 (3)	C20—C21—H21	119.9
CL2Bb—PT1Bb—Cl3B	176.1 (2)	C20—C21—C22	120.3 (5)
C14Bb—PT1Bb—Cl3B	94.2 (5)	C22—C21—H21	119.9
C15Bb—PT1Bb—Cl3B	84.1 (5)	C17—C22—C21	120.8 (5)
C15Aa—C14Aa—H14A	120.0	C17—C22—H22	119.6
PT1Aa—C14Aa—H14A	115.0	C21—C22—H22	119.6
H14Aa—C14Aa—H14B	120.0	C19—O23—C24	117.0 (4)
C15Aa—C14Aa—H14B	120.0	O23—C24—H24A	109.5
PT1Aa—C14Aa—H14B	82.4	N4—PT1Aa—Cl2A	90.11 (14)
C15Bb—PT1Bb—C14B	37.0 (4)	N4—PT1Bb—Cl2B	86.73 (18)
C15Bb—C14Bb—H14C	120.0	N4—PT1Aa—Cl3A	86.51 (14)
PT1Bb—C14Bb—H14C	116.1	N4—PT1Bb—Cl3B	90.1 (2)
PT1Bb—C14Bb—H14D	84.8	N4—PT1Aa—C14A	159.7 (3)
C15Bb—C14Bb—H14D	120.0	N4—PT1Bb—C14B	156.6 (4)
N4—C5—C6	125.1 (5)	N4—PT1Aa—C15A	162.7 (2)
C6—C5—H5	117.5	N4—PT1Bb—C15B	166.1 (4)
C5—C6—H6	121.5	C16—C15Aa—Pt1A	117.7 (4)
C7—C6—C5	117.0 (5)	C16—C15Bb—Pt1B	115.1 (8)
C7—C6—H6	121.5	C16—C15Bb—C14B	130.5 (14)
C6—C7—H7	120.1	C16—C15Aa—H15A	111.4
C6—C7—C8	119.7 (5)	C16—C15Bb—H15B	110.6
C8—C7—H7	120.1	O23—C24—H24B	109.5
C9—C8—C7	122.4 (5)	O23—C24—H24C	109.5
C13—C8—C7	118.5 (4)	H24A—C24—H24B	109.5
C13—C8—C9	119.0 (5)	H24A—C24—H24C	109.5
C8—C9—H9	119.5	H24B—C24—H24C	109.5
C10—C9—C8	121.1 (5)	C20—O25—C26	116.9 (4)
C10—C9—H9	119.5	O25—C26—H26A	110.1
C9—C10—H10	120.3	O25—C26—H26B	110.1
C9—C10—C11	119.4 (5)	O25—C26—C27	108.2 (4)
C11—C10—H10	120.3	H26A—C26—H26B	108.4
C10—C11—H11	118.4	C27—C26—H26A	110.1
C12—C11—C10	123.3 (5)	C27—C26—H26B	110.1
C12—C11—H11	118.4	O28—C27—C26	126.1 (4)
C11—C12—H12	121.3	O28—C27—O29	124.9 (5)
C11—C12—C13	117.4 (5)	O29—C27—C26	109.0 (4)
C13—C12—H12	121.3	C27—O29—C30	115.7 (4)
N4—C13—C8	120.6 (5)	O29—C30—H30A	110.3
N4—C13—C12	119.5 (4)	O29—C30—H30B	110.3
C8—C13—C12	119.9 (4)	O29—C30—C31	107.1 (4)
C17—C16—H16A	107.8	H30A—C30—H30B	108.6
C17—C16—H16B	107.8	C31—C30—H30A	110.3
C17—C16—H16C	107.1	C31—C30—H30B	110.3
C17—C16—H16D	107.1	C30—C31—H31A	109.1
H14Cb—C14Bb—H14D	120.0	C30—C31—H31B	109.1
C14Aa—PT1Aa—C15A	37.6 (3)	C30—C31—C32	112.6 (4)
C14Aa—C15Aa—H15A	111.4	H31A—C31—H31B	107.8
PT1Aa—C15Aa—H15A	111.4	C32—C31—H31A	109.1
C14Bb—C15Bb—H15B	110.6	C32—C31—H31B	109.1
PT1Bb—C15Bb—H15B	110.6	C31—C32—H32A	109.5
C14Aa—C15Aa—C16	128.8 (7)	C31—C32—H32B	109.5
C15Aa—C16—H16A	107.8	C31—C32—H32C	109.5
C15Aa—C16—H16B	107.8	H32A—C32—H32B	109.5
H16Aa—C16—H16B	107.2	H32A—C32—H32C	109.5
C15Bb—C16—H16C	107.1	H32B—C32—H32C	109.5

PT1Aa—N4—C5—C6	172.5 (4)	C10—C11—C12—C13	−0.9 (7)
PT1Bb—N4—C5—C6	−173.3 (4)	C11—C12—C13—N4	179.0 (4)
PT1Aa—N4—C13—C8	−172.7 (3)	C11—C12—C13—C8	0.3 (7)
PT1Bb—C14Bb—C15Bb—C16	109.1 (16)	C13—N4—C5—C6	−1.5 (8)
PT1Bb—N4—C13—C8	172.2 (4)	C13—C8—C9—C10	−1.6 (7)
PT1Aa—N4—C13—C12	8.6 (6)	C16—C17—C18—C19	179.7 (4)
PT1Bb—N4—C13—C12	−6.4 (6)	C16—C17—C22—C21	−179.4 (5)
C15Bb—C16—C17—C18	−51.0 (10)	C17—C18—C19—C20	−1.1 (7)
PT1Aa—C14Aa—C15Aa—C16	−109.6 (7)	C17—C18—C19—O23	179.1 (4)
PT1Aa—C15Aa—C16—C17	51.4 (7)	C18—C17—C22—C21	0.7 (7)
C14Bb—C15Bb—C16—C17	−136.9 (16)	C18—C19—C20—C21	2.3 (7)
C14Aa—C15Aa—C16—C17	136.3 (9)	C18—C19—C20—O25	−178.1 (4)
PT1Bb—C15Bb—C16—C17	−47.8 (11)	C18—C19—O23—C24	0.1 (7)
C15Aa—C16—C17—C18	−117.4 (6)	C19—C20—C21—C22	−2.1 (7)
N4—C5—C6—C7	0.3 (8)	C19—C20—O25—C26	175.4 (4)
C5—N4—C13—C8	1.0 (7)	C20—C19—O23—C24	−179.7 (4)
C5—N4—C13—C12	−177.6 (4)	C20—C21—C22—C17	0.6 (8)
C5—C6—C7—C8	1.2 (7)	C20—O25—C26—C27	−172.9 (4)
C6—C7—C8—C9	176.6 (5)	C21—C20—O25—C26	−5.0 (7)
C6—C7—C8—C13	−1.5 (7)	C22—C17—C18—C19	−0.4 (7)
C7—C8—C9—C10	−179.7 (5)	O23—C19—C20—C21	−177.8 (4)
C7—C8—C13—N4	0.4 (7)	O23—C19—C20—O25	1.8 (6)
C7—C8—C13—C12	179.1 (4)	O25—C20—C21—C22	178.4 (5)
C8—C9—C10—C11	1.1 (7)	O25—C26—C27—O28	7.9 (7)
C9—C8—C13—N4	−177.8 (4)	O25—C26—C27—O29	−174.2 (4)
C9—C8—C13—C12	0.9 (6)	C26—C27—O29—C30	−175.1 (4)
C9—C10—C11—C12	0.2 (8)	C27—O29—C30—C31	166.3 (4)
C15Bb—C16—C17—C22	129.1 (9)	O28—C27—O29—C30	2.9 (7)
C15Aa—C16—C17—C22	62.7 (7)	O29—C30—C31—C32	61.8 (6)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of ring C17–C22.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O28ⁱⁱ	0.95	2.47	3.404 (7)	169
C7—H7···O23ⁱⁱ	0.95	2.39	3.324 (7)	168
C24—H24B···O23ⁱⁱⁱⁱ	0.98	2.53	3.287 (6)	134
C12—H12···Cg1	0.95	2.93	3.732 (6)	142

Symmetry codes: (i) −x+2, −y+2, −z+1; (ii) −x+2, −y+1, −z+1.

[η²-4-Allyl-2-methoxy-1-(propoxycarbonylmethoxy)benzene]chlorido(quinolin-8-olato-κ²N,O)platinum(II) (chi30) top

Crystal data top

[Pt(C₉H₆NO)Cl(C₁₅H₂₀O₄)]	Z = 2
M_r = 639.00	F(000) = 624
Triclinic, P1	D_x = 1.900 Mg m⁻³
a = 8.3447 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.9191 (4) Å	Cell parameters from 12015 reflections
c = 12.9315 (5) Å	θ = 3.0–29.0°
α = 63.296 (4)°	µ = 6.44 mm⁻¹
β = 84.618 (3)°	T = 100 K
γ = 76.484 (3)°	Block, orange
V = 1117.09 (7) Å³	0.25 × 0.25 × 0.1 mm

Data collection top

Agilent SuperNova Dual Source diffractometer with an Eos detector	4564 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	4417 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.029
Detector resolution: 15.9631 pixels mm^-1	θ_max = 26.4°, θ_min = 2.8°
ω scans	h = −10→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	k = −14→14
T_min = 0.411, T_max = 1.000	l = −16→16
18255 measured reflections

Refinement top

Refinement on F²	Primary atom site location: heavy-atom method
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.021	H-atom parameters constrained
wR(F²) = 0.048	w = 1/[σ²(F_o²) + (0.0163P)² + 2.8225P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max = 0.002
4564 reflections	Δρ_max = 2.18 e Å⁻³
291 parameters	Δρ_min = −1.45 e Å⁻³
0 restraints

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Pt1	0.04044 (2)	0.99699 (2)	0.32891 (2)	0.01151 (5)
Cl13	0.16523 (10)	1.14992 (8)	0.18856 (7)	0.01867 (17)
O12	−0.0616 (3)	0.8637 (2)	0.4578 (2)	0.0154 (5)
O23	0.2621 (3)	0.5145 (2)	0.3564 (2)	0.0176 (5)
O25	0.2664 (3)	0.5075 (2)	0.1596 (2)	0.0146 (5)
O28	0.4923 (3)	0.3181 (3)	0.1420 (2)	0.0255 (6)
O29	0.3771 (3)	0.3538 (2)	−0.02330 (19)	0.0153 (5)
N2	0.2441 (3)	0.9061 (2)	0.4345 (2)	0.0112 (5)
C3	0.3926 (4)	0.9321 (3)	0.4188 (3)	0.0146 (7)
H3	0.4123	1.0059	0.3522	0.017*
C4	0.5220 (4)	0.8532 (3)	0.4986 (3)	0.0154 (7)
H4	0.6274	0.8743	0.4859	0.018*
C5	0.4963 (4)	0.7459 (3)	0.5946 (3)	0.0136 (7)
H5	0.5837	0.6924	0.6485	0.016*
C6	0.3385 (4)	0.7147 (3)	0.6136 (3)	0.0123 (6)
C7	0.2995 (4)	0.6068 (3)	0.7088 (3)	0.0151 (7)
H7	0.3812	0.5480	0.7655	0.018*
C8	0.1415 (4)	0.5875 (3)	0.7187 (3)	0.0179 (7)
H8	0.1156	0.5142	0.7830	0.022*
C9	0.0163 (4)	0.6730 (3)	0.6365 (3)	0.0167 (7)
H9	−0.0917	0.6570	0.6465	0.020*
C10	0.0502 (4)	0.7797 (3)	0.5419 (3)	0.0125 (6)
C11	0.2137 (4)	0.7999 (3)	0.5310 (3)	0.0112 (6)
C14	−0.1965 (4)	1.1023 (3)	0.2518 (3)	0.0168 (7)
H14A	−0.2815	1.0850	0.3047	0.020*
H14B	−0.1540	1.1746	0.2327	0.020*
C15	−0.1322 (4)	1.0206 (3)	0.2011 (3)	0.0145 (7)
H15	−0.0979	1.0643	0.1209	0.017*
C16	−0.1942 (4)	0.9026 (3)	0.2278 (3)	0.0160 (7)
H16A	−0.2944	0.9280	0.1802	0.019*
H16B	−0.2267	0.8654	0.3100	0.019*
C17	−0.0716 (4)	0.7992 (3)	0.2064 (3)	0.0136 (7)
C18	0.0381 (4)	0.7055 (3)	0.2943 (3)	0.0144 (7)
H18	0.0358	0.7070	0.3673	0.017*
C19	0.1504 (4)	0.6104 (3)	0.2758 (3)	0.0132 (7)
C20	0.1528 (4)	0.6070 (3)	0.1684 (3)	0.0116 (6)
C21	0.0445 (4)	0.6995 (3)	0.0812 (3)	0.0140 (7)
H21	0.0452	0.6976	0.0085	0.017*
C22	−0.0659 (4)	0.7957 (3)	0.1008 (3)	0.0144 (7)
H22	−0.1385	0.8602	0.0402	0.017*
C24	0.2638 (5)	0.5115 (4)	0.4676 (3)	0.0289 (9)
H24A	0.3460	0.4367	0.5173	0.043*
H24B	0.1547	0.5054	0.5022	0.043*
H24C	0.2919	0.5902	0.4598	0.043*
C26	0.2514 (4)	0.4874 (3)	0.0616 (3)	0.0146 (7)
H26A	0.2601	0.5658	−0.0102	0.018*
H26B	0.1429	0.4673	0.0611	0.018*
C27	0.3883 (4)	0.3763 (3)	0.0677 (3)	0.0134 (7)
C30	0.5000 (5)	0.2451 (3)	−0.0251 (3)	0.0227 (8)
H30A	0.4733	0.1632	0.0331	0.027*
H30B	0.6105	0.2487	−0.0065	0.027*
C31	0.4988 (5)	0.2527 (4)	−0.1449 (3)	0.0252 (8)
H31A	0.3863	0.2547	−0.1651	0.030*
H31B	0.5313	0.3327	−0.2023	0.030*
C32	0.6175 (5)	0.1375 (4)	−0.1479 (4)	0.0294 (9)
H32A	0.7285	0.1359	−0.1276	0.044*
H32B	0.6177	0.1431	−0.2259	0.044*
H32C	0.5833	0.0588	−0.0922	0.044*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pt1	0.01206 (7)	0.01043 (7)	0.01114 (7)	0.00036 (5)	−0.00234 (5)	−0.00484 (5)
Cl13	0.0219 (4)	0.0151 (4)	0.0148 (4)	−0.0047 (3)	−0.0009 (3)	−0.0023 (3)
O12	0.0083 (11)	0.0158 (12)	0.0217 (13)	−0.0014 (9)	−0.0011 (9)	−0.0082 (10)
O23	0.0211 (12)	0.0163 (12)	0.0153 (12)	0.0041 (10)	−0.0066 (10)	−0.0094 (10)
O25	0.0152 (11)	0.0143 (11)	0.0150 (12)	0.0034 (9)	−0.0024 (9)	−0.0097 (10)
O28	0.0191 (13)	0.0301 (15)	0.0315 (15)	0.0090 (11)	−0.0115 (11)	−0.0217 (13)
O29	0.0192 (12)	0.0137 (11)	0.0117 (12)	0.0025 (9)	−0.0004 (9)	−0.0074 (9)
N2	0.0153 (13)	0.0102 (13)	0.0099 (13)	−0.0015 (11)	0.0012 (11)	−0.0068 (11)
C3	0.0163 (16)	0.0157 (16)	0.0138 (17)	−0.0052 (13)	0.0020 (13)	−0.0078 (14)
C4	0.0112 (15)	0.0200 (17)	0.0183 (18)	−0.0039 (13)	0.0015 (13)	−0.0113 (14)
C5	0.0122 (15)	0.0149 (16)	0.0144 (17)	0.0028 (13)	−0.0034 (13)	−0.0090 (13)
C6	0.0155 (16)	0.0113 (15)	0.0121 (16)	0.0004 (12)	−0.0016 (12)	−0.0082 (13)
C7	0.0202 (17)	0.0131 (16)	0.0108 (16)	−0.0003 (13)	−0.0024 (13)	−0.0054 (13)
C8	0.0253 (18)	0.0150 (16)	0.0125 (17)	−0.0065 (14)	0.0029 (14)	−0.0048 (14)
C9	0.0168 (16)	0.0188 (17)	0.0161 (17)	−0.0062 (14)	0.0031 (13)	−0.0085 (14)
C10	0.0144 (15)	0.0127 (15)	0.0120 (16)	−0.0006 (12)	0.0002 (12)	−0.0078 (13)
C11	0.0139 (15)	0.0120 (15)	0.0108 (16)	−0.0022 (12)	0.0011 (12)	−0.0081 (13)
C14	0.0139 (16)	0.0171 (17)	0.0195 (18)	0.0022 (13)	−0.0071 (13)	−0.0095 (14)
C15	0.0115 (15)	0.0162 (16)	0.0143 (17)	0.0014 (13)	−0.0057 (13)	−0.0063 (14)
C16	0.0114 (15)	0.0185 (17)	0.0169 (17)	0.0014 (13)	−0.0015 (13)	−0.0085 (14)
C17	0.0099 (15)	0.0116 (15)	0.0199 (18)	−0.0019 (12)	0.0000 (13)	−0.0076 (14)
C18	0.0147 (16)	0.0158 (16)	0.0157 (17)	−0.0031 (13)	−0.0003 (13)	−0.0094 (14)
C19	0.0117 (15)	0.0114 (15)	0.0173 (17)	−0.0024 (12)	−0.0013 (13)	−0.0067 (13)
C20	0.0102 (14)	0.0095 (15)	0.0152 (17)	−0.0028 (12)	0.0030 (12)	−0.0056 (13)
C21	0.0143 (15)	0.0151 (16)	0.0126 (16)	−0.0032 (13)	0.0010 (13)	−0.0063 (13)
C22	0.0125 (15)	0.0109 (15)	0.0167 (17)	−0.0007 (12)	−0.0022 (13)	−0.0037 (13)
C24	0.035 (2)	0.030 (2)	0.021 (2)	0.0109 (18)	−0.0132 (17)	−0.0170 (17)
C26	0.0141 (16)	0.0143 (16)	0.0141 (17)	0.0002 (13)	−0.0007 (13)	−0.0065 (14)
C27	0.0122 (15)	0.0121 (15)	0.0163 (17)	−0.0036 (13)	0.0020 (13)	−0.0065 (13)
C30	0.0223 (18)	0.0186 (18)	0.027 (2)	−0.0013 (15)	0.0014 (15)	−0.0112 (16)
C31	0.0216 (19)	0.029 (2)	0.030 (2)	−0.0067 (16)	0.0041 (16)	−0.0184 (18)
C32	0.028 (2)	0.030 (2)	0.037 (2)	−0.0081 (17)	0.0065 (18)	−0.0201 (19)

Geometric parameters (Å, º) top

Pt1—Cl13	2.2935 (8)	C14—H14B	0.9296
Pt1—O12	2.003 (2)	C14—C15	1.389 (5)
Pt1—N2	2.042 (3)	C15—H15	0.9789
Pt1—C14	2.136 (3)	C15—C16	1.495 (5)
Pt1—C15	2.174 (3)	C16—H16A	0.9900
O12—C10	1.353 (4)	C16—H16B	0.9900
O23—C19	1.370 (4)	C16—C17	1.519 (4)
O23—C24	1.423 (4)	C17—C18	1.398 (5)
O25—C20	1.376 (4)	C17—C22	1.380 (5)
O25—C26	1.413 (4)	C18—H18	0.9500
O28—C27	1.198 (4)	C18—C19	1.388 (5)
O29—C27	1.334 (4)	C19—C20	1.405 (5)
O29—C30	1.461 (4)	C20—C21	1.383 (4)
N2—C3	1.323 (4)	C21—H21	0.9500
N2—C11	1.376 (4)	C21—C22	1.397 (5)
C3—H3	0.9500	C22—H22	0.9500
C3—C4	1.406 (5)	C24—H24A	0.9800
C4—H4	0.9500	C24—H24B	0.9800
C4—C5	1.369 (5)	C24—H24C	0.9800
C5—H5	0.9500	C26—H26A	0.9900
C5—C6	1.421 (5)	C26—H26B	0.9900
C6—C7	1.404 (5)	C26—C27	1.510 (4)
C6—C11	1.413 (4)	C30—H30A	0.9900
C7—H7	0.9500	C30—H30B	0.9900
C7—C8	1.376 (5)	C30—C31	1.511 (5)
C8—H8	0.9500	C31—H31A	0.9900
C8—C9	1.413 (5)	C31—H31B	0.9900
C9—H9	0.9500	C31—C32	1.508 (5)
C9—C10	1.378 (5)	C32—H32A	0.9800
C10—C11	1.423 (4)	C32—H32B	0.9800
C14—H14A	0.9291	C32—H32C	0.9800

O12—Pt1—Cl13	176.98 (7)	C15—C16—H16B	108.6
O12—Pt1—N2	82.92 (10)	C15—C16—C17	114.8 (3)
O12—Pt1—C14	90.86 (12)	H16A—C16—H16B	107.5
O12—Pt1—C15	92.59 (11)	C17—C16—H16A	108.6
N2—Pt1—Cl13	94.62 (8)	C17—C16—H16B	108.6
N2—Pt1—C14	166.29 (12)	C18—C17—C16	120.0 (3)
N2—Pt1—C15	154.39 (11)	C22—C17—C16	121.1 (3)
C14—Pt1—Cl13	91.17 (10)	C22—C17—C18	118.9 (3)
C14—Pt1—C15	37.59 (13)	C17—C18—H18	119.8
C15—Pt1—Cl13	90.38 (9)	C19—C18—C17	120.5 (3)
C10—O12—Pt1	111.51 (19)	C19—C18—H18	119.8
C19—O23—C24	118.0 (3)	O23—C19—C18	124.8 (3)
C20—O25—C26	116.5 (2)	O23—C19—C20	115.3 (3)
C27—O29—C30	114.8 (3)	C18—C19—C20	119.9 (3)
C3—N2—Pt1	129.5 (2)	O25—C20—C19	115.4 (3)
C3—N2—C11	119.8 (3)	O25—C20—C21	124.8 (3)
C11—N2—Pt1	110.6 (2)	C21—C20—C19	119.8 (3)
N2—C3—H3	119.2	C20—C21—H21	120.2
N2—C3—C4	121.5 (3)	C20—C21—C22	119.5 (3)
C4—C3—H3	119.2	C22—C21—H21	120.2
C3—C4—H4	120.0	C17—C22—C21	121.4 (3)
C5—C4—C3	120.0 (3)	C17—C22—H22	119.3
C5—C4—H4	120.0	C21—C22—H22	119.3
C4—C5—H5	120.1	O23—C24—H24A	109.5
C4—C5—C6	119.9 (3)	O23—C24—H24B	109.5
C6—C5—H5	120.1	O23—C24—H24C	109.5
C7—C6—C5	124.3 (3)	H24A—C24—H24B	109.5
C7—C6—C11	118.8 (3)	H24A—C24—H24C	109.5
C11—C6—C5	116.9 (3)	H24B—C24—H24C	109.5
C6—C7—H7	120.5	O25—C26—H26A	110.1
C8—C7—C6	119.1 (3)	O25—C26—H26B	110.1
C8—C7—H7	120.5	O25—C26—C27	108.0 (3)
C7—C8—H8	118.9	H26A—C26—H26B	108.4
C7—C8—C9	122.2 (3)	C27—C26—H26A	110.1
C9—C8—H8	118.9	C27—C26—H26B	110.1
C8—C9—H9	119.8	O28—C27—O29	125.1 (3)
C10—C9—C8	120.3 (3)	O28—C27—C26	125.3 (3)
C10—C9—H9	119.8	O29—C27—C26	109.6 (3)
O12—C10—C9	123.7 (3)	O29—C30—H30A	110.1
O12—C10—C11	118.5 (3)	O29—C30—H30B	110.1
C9—C10—C11	117.7 (3)	O29—C30—C31	108.1 (3)
N2—C11—C6	121.8 (3)	H30A—C30—H30B	108.4
N2—C11—C10	116.2 (3)	C31—C30—H30A	110.1
C6—C11—C10	121.9 (3)	C31—C30—H30B	110.1
Pt1—C14—H14A	112.7	C30—C31—H31A	109.8
Pt1—C14—H14B	84.8	C30—C31—H31B	109.8
H14A—C14—H14B	120.0	H31A—C31—H31B	108.2
C15—C14—Pt1	72.67 (19)	C32—C31—C30	109.5 (3)
C15—C14—H14A	120.4	C32—C31—H31A	109.8
C15—C14—H14B	119.7	C32—C31—H31B	109.8
Pt1—C15—H15	114.1	C31—C32—H32A	109.5
C14—C15—Pt1	69.75 (19)	C31—C32—H32B	109.5
C14—C15—H15	114.2	C31—C32—H32C	109.5
C14—C15—C16	122.6 (3)	H32A—C32—H32B	109.5
C16—C15—Pt1	114.4 (2)	H32A—C32—H32C	109.5
C16—C15—H15	114.2	H32B—C32—H32C	109.5
C15—C16—H16A	108.6

Pt1—O12—C10—C9	−175.2 (3)	C8—C9—C10—O12	177.9 (3)
Pt1—O12—C10—C11	3.0 (3)	C8—C9—C10—C11	−0.3 (5)
Pt1—N2—C3—C4	−175.9 (2)	C9—C10—C11—N2	178.9 (3)
Pt1—N2—C11—C6	175.2 (2)	C9—C10—C11—C6	−0.1 (5)
Pt1—N2—C11—C10	−3.8 (3)	C11—N2—C3—C4	0.4 (5)
Pt1—C14—C15—C16	106.6 (3)	C11—C6—C7—C8	−0.1 (5)
Pt1—C15—C16—C17	−75.3 (3)	C14—C15—C16—C17	−156.0 (3)
O12—C10—C11—N2	0.6 (4)	C15—C16—C17—C18	88.9 (4)
O12—C10—C11—C6	−178.4 (3)	C15—C16—C17—C22	−91.0 (4)
O23—C19—C20—O25	0.3 (4)	C16—C17—C18—C19	179.9 (3)
O23—C19—C20—C21	179.9 (3)	C16—C17—C22—C21	−178.8 (3)
O25—C20—C21—C22	179.7 (3)	C17—C18—C19—O23	−179.8 (3)
O25—C26—C27—O28	−1.3 (5)	C17—C18—C19—C20	−0.8 (5)
O25—C26—C27—O29	179.5 (3)	C18—C17—C22—C21	1.3 (5)
O29—C30—C31—C32	−176.7 (3)	C18—C19—C20—O25	−178.7 (3)
N2—C3—C4—C5	0.5 (5)	C18—C19—C20—C21	0.8 (5)
C3—N2—C11—C6	−1.7 (5)	C19—C20—C21—C22	0.2 (5)
C3—N2—C11—C10	179.3 (3)	C20—O25—C26—C27	179.0 (3)
C3—C4—C5—C6	−0.1 (5)	C20—C21—C22—C17	−1.3 (5)
C4—C5—C6—C7	179.7 (3)	C22—C17—C18—C19	−0.3 (5)
C4—C5—C6—C11	−1.1 (5)	C24—O23—C19—C18	0.1 (5)
C5—C6—C7—C8	179.1 (3)	C24—O23—C19—C20	−178.9 (3)
C5—C6—C11—N2	2.0 (5)	C26—O25—C20—C19	168.6 (3)
C5—C6—C11—C10	−179.0 (3)	C26—O25—C20—C21	−10.9 (4)
C6—C7—C8—C9	−0.3 (5)	C27—O29—C30—C31	−166.0 (3)
C7—C6—C11—N2	−178.7 (3)	C30—O29—C27—O28	2.8 (5)
C7—C6—C11—C10	0.3 (5)	C30—O29—C27—C26	−178.0 (3)
C7—C8—C9—C10	0.5 (5)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of ring C6–C11, Cg2 is the centroid of ring N2/C3–C6/C11 and Cg3 is the centroid of ring C17–C22.

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16B···O12	0.99	2.45	3.070 (4)	120
C18—H18···O12	0.95	2.57	3.352 (5)	140
C4—H4···O12ⁱ	0.95	2.57	3.488 (4)	163
C14—H14A···Cg2ⁱⁱ	0.93	2.94	3.581 (4)	127
C14—H14B···Cg1ⁱⁱ	0.93	2.88	3.493 (4)	125
C24—H24C···Cg1	0.98	2.91	3.513 (5)	121
C32—H32A···Cg3ⁱⁱⁱ	0.98	2.84	3.655 (5)	141

Symmetry codes: (i) x+1, y, z; (ii) −x, −y+2, −z+1; (iii) −x+1, −y+1, −z.

{η²-4-Allyl-2-methoxy-1-[(propan-2-yloxy)carbonylmethoxy]benzene}chlorido(quinolin-8-olato-κ²N,O)platinum(II) (chi9) top

Crystal data top

[Pt(C₉H₆NO)Cl(C₁₅H₂₀O₄)]	Z = 2
M_r = 639.00	F(000) = 624
Triclinic, P1	D_x = 1.830 Mg m⁻³
a = 9.7858 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.0447 (2) Å	Cell parameters from 30804 reflections
c = 11.8117 (3) Å	θ = 3.3–29.2°
α = 85.059 (2)°	µ = 6.20 mm⁻¹
β = 73.685 (3)°	T = 200 K
γ = 71.139 (2)°	Block, yellow
V = 1159.41 (6) Å³	0.3 × 0.25 × 0.15 mm

Data collection top

Agilent SuperNova Dual Source diffractometer with an Eos detector	4738 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	4534 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.037
Detector resolution: 15.9631 pixels mm^-1	θ_max = 26.4°, θ_min = 2.7°
ω scans	h = −12→12
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	k = −13→13
T_min = 0.369, T_max = 1.000	l = −14→14
47800 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.017	H-atom parameters constrained
wR(F²) = 0.041	w = 1/[σ²(F_o²) + (0.0139P)² + 1.3246P] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max = 0.001
4738 reflections	Δρ_max = 1.46 e Å⁻³
292 parameters	Δρ_min = −1.01 e Å⁻³
0 restraints

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C3	−0.1859 (3)	0.5736 (3)	0.8919 (3)	0.0312 (6)
H3	−0.136026	0.551246	0.952579	0.037*
C4	−0.1698 (3)	0.6780 (3)	0.8191 (3)	0.0371 (7)
H4	−0.109806	0.725613	0.831437	0.044*
C5	−0.2395 (3)	0.7118 (3)	0.7307 (3)	0.0325 (6)
H5	−0.228789	0.782996	0.681875	0.039*
C6	−0.3279 (3)	0.6399 (3)	0.7125 (2)	0.0291 (6)
C7	−0.4021 (4)	0.6640 (3)	0.6226 (3)	0.0375 (7)
H7	−0.392972	0.730819	0.567552	0.045*
C8	−0.4877 (4)	0.5894 (3)	0.6156 (3)	0.0428 (8)
H8	−0.538702	0.606963	0.555603	0.051*
C9	−0.5029 (4)	0.4884 (3)	0.6935 (3)	0.0391 (7)
H9	−0.563451	0.439284	0.685632	0.047*
C10	−0.4298 (3)	0.4602 (3)	0.7819 (2)	0.0283 (6)
C11	−0.3416 (3)	0.5375 (2)	0.7905 (2)	0.0241 (5)
C14	−0.3857 (4)	0.2014 (3)	1.0626 (3)	0.0399 (7)
H14A	−0.378315	0.190373	1.144981	0.048*
H14B	−0.482399	0.198555	1.054109	0.048*
C15	−0.2573 (4)	0.1376 (3)	0.9756 (3)	0.0346 (7)
H15	−0.168809	0.090147	1.005924	0.042*
C16	−0.2630 (3)	0.0802 (3)	0.8671 (3)	0.0365 (7)
H16A	−0.351713	0.134864	0.842030	0.044*
H16B	−0.276076	−0.005014	0.886936	0.044*
C17	−0.1239 (3)	0.0657 (3)	0.7646 (3)	0.0311 (6)
C18	−0.1177 (3)	0.1623 (3)	0.6802 (3)	0.0325 (6)
H18	−0.201221	0.237708	0.687036	0.039*
C19	0.0092 (3)	0.1488 (3)	0.5867 (2)	0.0300 (6)
C20	0.1327 (3)	0.0372 (3)	0.5753 (2)	0.0289 (6)
C21	0.1276 (3)	−0.0571 (3)	0.6586 (3)	0.0342 (6)
H21	0.210996	−0.132599	0.652078	0.041*
C22	−0.0004 (4)	−0.0419 (3)	0.7529 (3)	0.0354 (7)
H22	−0.002276	−0.107384	0.810518	0.042*
C24	−0.0978 (4)	0.3521 (3)	0.5056 (3)	0.0555 (10)
H24A	−0.073160	0.405287	0.436914	0.083*
H24B	−0.117973	0.399543	0.577958	0.083*
H24C	−0.186798	0.329817	0.505151	0.083*
C26	0.3687 (3)	−0.0846 (3)	0.4582 (3)	0.0316 (6)
H26A	0.329614	−0.150676	0.439842	0.038*
H26B	0.404777	−0.111460	0.529549	0.038*
C27	0.4958 (3)	−0.0715 (3)	0.3562 (3)	0.0294 (6)
C30	0.7357 (3)	−0.1960 (3)	0.2374 (3)	0.0379 (7)
H30	0.772178	−0.124178	0.248467	0.046*
C31	0.7087 (4)	−0.1866 (4)	0.1172 (3)	0.0512 (9)
H31A	0.803987	−0.198775	0.056507	0.077*
H31B	0.639097	−0.102057	0.108053	0.077*
H31C	0.665597	−0.252856	0.108640	0.077*
C32	0.8458 (4)	−0.3219 (3)	0.2587 (4)	0.0555 (10)
H32A	0.815462	−0.392474	0.240074	0.083*
H32B	0.847282	−0.327029	0.341567	0.083*
H32C	0.946136	−0.327789	0.208108	0.083*
Cl13	−0.14543 (9)	0.33203 (8)	1.08003 (7)	0.04446 (19)
N2	−0.2692 (2)	0.5055 (2)	0.87781 (19)	0.0254 (5)
O12	−0.4363 (2)	0.36373 (18)	0.85739 (18)	0.0314 (4)
O23	0.0252 (2)	0.23816 (19)	0.50069 (18)	0.0411 (5)
O25	0.2535 (2)	0.03400 (18)	0.47921 (18)	0.0354 (5)
O28	0.5090 (3)	0.0266 (2)	0.3106 (2)	0.0453 (6)
O29	0.5949 (2)	−0.18764 (18)	0.32815 (18)	0.0323 (4)
Pt1	−0.29907 (2)	0.34304 (2)	0.96161 (2)	0.02646 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C3	0.0306 (15)	0.0285 (14)	0.0353 (16)	−0.0075 (12)	−0.0114 (12)	−0.0024 (12)
C4	0.0318 (16)	0.0302 (15)	0.0499 (19)	−0.0122 (13)	−0.0086 (14)	−0.0014 (13)
C5	0.0315 (15)	0.0225 (14)	0.0339 (16)	−0.0042 (12)	0.0009 (12)	0.0019 (11)
C6	0.0298 (14)	0.0228 (13)	0.0235 (13)	0.0014 (11)	−0.0005 (11)	−0.0017 (10)
C7	0.0478 (19)	0.0263 (15)	0.0299 (15)	0.0003 (13)	−0.0120 (14)	0.0033 (12)
C8	0.050 (2)	0.0377 (17)	0.0386 (18)	0.0019 (15)	−0.0258 (16)	−0.0024 (14)
C9	0.0384 (17)	0.0368 (17)	0.0458 (19)	−0.0071 (14)	−0.0209 (15)	−0.0047 (14)
C10	0.0250 (14)	0.0243 (14)	0.0309 (15)	−0.0011 (11)	−0.0071 (11)	−0.0020 (11)
C11	0.0217 (13)	0.0198 (12)	0.0241 (13)	0.0002 (10)	−0.0024 (10)	−0.0034 (10)
C14	0.0438 (18)	0.0311 (16)	0.0331 (16)	−0.0125 (14)	0.0061 (14)	0.0092 (13)
C15	0.0405 (17)	0.0235 (14)	0.0291 (15)	−0.0068 (12)	0.0012 (13)	0.0080 (11)
C16	0.0381 (17)	0.0280 (15)	0.0395 (17)	−0.0132 (13)	−0.0015 (14)	0.0031 (12)
C17	0.0365 (16)	0.0249 (14)	0.0298 (15)	−0.0122 (12)	−0.0025 (12)	−0.0010 (11)
C18	0.0339 (16)	0.0245 (14)	0.0315 (15)	−0.0041 (12)	−0.0025 (12)	−0.0013 (11)
C19	0.0344 (15)	0.0239 (14)	0.0250 (14)	−0.0040 (12)	−0.0040 (12)	0.0008 (11)
C20	0.0315 (15)	0.0267 (14)	0.0236 (14)	−0.0054 (12)	−0.0038 (11)	−0.0014 (11)
C21	0.0393 (17)	0.0234 (14)	0.0335 (16)	−0.0037 (12)	−0.0072 (13)	0.0013 (12)
C22	0.0471 (18)	0.0239 (14)	0.0315 (15)	−0.0127 (13)	−0.0044 (13)	0.0046 (12)
C24	0.047 (2)	0.0341 (18)	0.055 (2)	0.0089 (15)	0.0041 (17)	0.0179 (16)
C26	0.0308 (15)	0.0239 (14)	0.0321 (15)	−0.0009 (12)	−0.0045 (12)	−0.0012 (11)
C27	0.0280 (14)	0.0255 (14)	0.0327 (15)	−0.0040 (11)	−0.0090 (12)	−0.0045 (12)
C30	0.0269 (15)	0.0352 (16)	0.0465 (18)	−0.0092 (13)	0.0004 (13)	−0.0089 (14)
C31	0.043 (2)	0.063 (2)	0.0398 (19)	−0.0156 (17)	0.0024 (15)	−0.0077 (17)
C32	0.0304 (18)	0.046 (2)	0.079 (3)	−0.0011 (15)	−0.0075 (18)	−0.0070 (19)
Cl13	0.0453 (4)	0.0485 (5)	0.0394 (4)	−0.0074 (4)	−0.0220 (4)	0.0084 (3)
N2	0.0240 (11)	0.0230 (11)	0.0254 (11)	−0.0037 (9)	−0.0051 (9)	−0.0001 (9)
O12	0.0292 (10)	0.0289 (10)	0.0366 (11)	−0.0113 (8)	−0.0084 (9)	0.0047 (8)
O23	0.0392 (12)	0.0298 (11)	0.0312 (11)	0.0048 (9)	0.0052 (9)	0.0103 (9)
O25	0.0327 (11)	0.0249 (10)	0.0319 (11)	0.0027 (8)	0.0027 (9)	0.0035 (8)
O28	0.0419 (13)	0.0243 (11)	0.0556 (15)	−0.0047 (9)	0.0018 (11)	0.0018 (10)
O29	0.0286 (10)	0.0247 (10)	0.0363 (11)	−0.0037 (8)	−0.0018 (9)	−0.0033 (8)
Pt1	0.02589 (6)	0.02385 (6)	0.02392 (6)	−0.00394 (4)	−0.00313 (4)	0.00299 (4)

Geometric parameters (Å, º) top

C3—H3	0.9500	C18—C19	1.387 (4)
C3—C4	1.401 (4)	C19—C20	1.404 (4)
C3—N2	1.323 (3)	C19—O23	1.367 (3)
C4—H4	0.9500	C20—C21	1.374 (4)
C4—C5	1.365 (4)	C20—O25	1.383 (3)
C5—H5	0.9500	C21—H21	0.9500
C5—C6	1.416 (4)	C21—C22	1.397 (4)
C6—C7	1.410 (4)	C22—H22	0.9500
C6—C11	1.413 (4)	C24—H24A	0.9800
C7—H7	0.9500	C24—H24B	0.9800
C7—C8	1.372 (5)	C24—H24C	0.9800
C8—H8	0.9500	C24—O23	1.424 (4)
C8—C9	1.403 (5)	C26—H26A	0.9900
C9—H9	0.9500	C26—H26B	0.9900
C9—C10	1.385 (4)	C26—C27	1.505 (4)
C10—C11	1.423 (4)	C26—O25	1.411 (3)
C10—O12	1.335 (3)	C27—O28	1.196 (3)
C11—N2	1.370 (3)	C27—O29	1.336 (3)
C14—H14A	0.9900	C30—H30	1.0000
C14—H14B	0.9900	C30—C31	1.505 (5)
C14—C15	1.400 (4)	C30—C32	1.510 (5)
C14—Pt1	2.134 (3)	C30—O29	1.470 (3)
C15—H15	1.0000	C31—H31A	0.9800
C15—C16	1.501 (4)	C31—H31B	0.9800
C15—Pt1	2.172 (3)	C31—H31C	0.9800
C16—H16A	0.9900	C32—H32A	0.9800
C16—H16B	0.9900	C32—H32B	0.9800
C16—C17	1.520 (4)	C32—H32C	0.9800
C17—C18	1.400 (4)	Cl13—Pt1	2.2947 (8)
C17—C22	1.378 (4)	N2—Pt1	2.039 (2)
C18—H18	0.9500	O12—Pt1	2.0135 (19)

C4—C3—H3	119.3	C20—C21—H21	120.1
N2—C3—H3	119.3	C20—C21—C22	119.9 (3)
N2—C3—C4	121.5 (3)	C22—C21—H21	120.1
C3—C4—H4	119.7	C17—C22—C21	121.6 (3)
C5—C4—C3	120.5 (3)	C17—C22—H22	119.2
C5—C4—H4	119.7	C21—C22—H22	119.2
C4—C5—H5	120.3	H24A—C24—H24B	109.5
C4—C5—C6	119.4 (3)	H24A—C24—H24C	109.5
C6—C5—H5	120.3	H24B—C24—H24C	109.5
C7—C6—C5	124.4 (3)	O23—C24—H24A	109.5
C7—C6—C11	118.5 (3)	O23—C24—H24B	109.5
C11—C6—C5	117.1 (3)	O23—C24—H24C	109.5
C6—C7—H7	120.5	H26A—C26—H26B	108.3
C8—C7—C6	119.0 (3)	C27—C26—H26A	109.8
C8—C7—H7	120.5	C27—C26—H26B	109.8
C7—C8—H8	118.7	O25—C26—H26A	109.8
C7—C8—C9	122.7 (3)	O25—C26—H26B	109.8
C9—C8—H8	118.7	O25—C26—C27	109.3 (2)
C8—C9—H9	119.9	O28—C27—C26	125.9 (3)
C10—C9—C8	120.2 (3)	O28—C27—O29	125.6 (3)
C10—C9—H9	119.9	O29—C27—C26	108.4 (2)
C9—C10—C11	117.6 (3)	C31—C30—H30	109.5
O12—C10—C9	123.4 (3)	C31—C30—C32	113.5 (3)
O12—C10—C11	118.9 (2)	C32—C30—H30	109.5
C6—C11—C10	122.0 (2)	O29—C30—H30	109.5
N2—C11—C6	122.0 (2)	O29—C30—C31	109.4 (3)
N2—C11—C10	116.0 (2)	O29—C30—C32	105.4 (3)
H14A—C14—H14B	113.3	C30—C31—H31A	109.5
C15—C14—H14A	116.3	C30—C31—H31B	109.5
C15—C14—H14B	116.3	C30—C31—H31C	109.5
C15—C14—Pt1	72.51 (16)	H31A—C31—H31B	109.5
Pt1—C14—H14A	116.3	H31A—C31—H31C	109.5
Pt1—C14—H14B	116.3	H31B—C31—H31C	109.5
C14—C15—H15	114.5	C30—C32—H32A	109.5
C14—C15—C16	123.1 (3)	C30—C32—H32B	109.5
C14—C15—Pt1	69.57 (16)	C30—C32—H32C	109.5
C16—C15—H15	114.5	H32A—C32—H32B	109.5
C16—C15—Pt1	112.57 (19)	H32A—C32—H32C	109.5
Pt1—C15—H15	114.5	H32B—C32—H32C	109.5
C15—C16—H16A	108.8	C3—N2—C11	119.5 (2)
C15—C16—H16B	108.8	C3—N2—Pt1	129.50 (19)
C15—C16—C17	113.6 (3)	C11—N2—Pt1	110.82 (17)
H16A—C16—H16B	107.7	C10—O12—Pt1	111.41 (16)
C17—C16—H16A	108.8	C19—O23—C24	118.1 (2)
C17—C16—H16B	108.8	C20—O25—C26	115.3 (2)
C18—C17—C16	120.7 (3)	C27—O29—C30	117.6 (2)
C22—C17—C16	121.0 (3)	C14—Pt1—C15	37.92 (11)
C22—C17—C18	118.3 (3)	C14—Pt1—Cl13	92.02 (10)
C17—C18—H18	119.7	C15—Pt1—Cl13	90.47 (9)
C19—C18—C17	120.6 (3)	N2—Pt1—C14	166.07 (11)
C19—C18—H18	119.7	N2—Pt1—C15	153.86 (10)
C18—C19—C20	120.2 (3)	N2—Pt1—Cl13	94.65 (7)
O23—C19—C18	124.5 (3)	O12—Pt1—C14	90.51 (11)
O23—C19—C20	115.3 (2)	O12—Pt1—C15	92.84 (10)
C21—C20—C19	119.4 (3)	O12—Pt1—Cl13	176.69 (6)
C21—C20—O25	125.2 (3)	O12—Pt1—N2	82.43 (8)
O25—C20—C19	115.4 (2)

C3—C4—C5—C6	−0.4 (4)	C17—C18—C19—C20	0.5 (4)
C4—C3—N2—C11	−0.1 (4)	C17—C18—C19—O23	−179.8 (3)
C4—C3—N2—Pt1	174.8 (2)	C18—C17—C22—C21	−1.3 (4)
C4—C5—C6—C7	−178.5 (3)	C18—C19—C20—C21	−1.2 (4)
C4—C5—C6—C11	1.5 (4)	C18—C19—C20—O25	−179.7 (3)
C5—C6—C7—C8	−178.4 (3)	C18—C19—O23—C24	−1.3 (5)
C5—C6—C11—C10	178.8 (2)	C19—C20—C21—C22	0.6 (4)
C5—C6—C11—N2	−2.1 (4)	C19—C20—O25—C26	−171.4 (2)
C6—C7—C8—C9	−1.0 (5)	C20—C19—O23—C24	178.4 (3)
C6—C11—N2—C3	1.3 (4)	C20—C21—C22—C17	0.7 (5)
C6—C11—N2—Pt1	−174.45 (19)	C21—C20—O25—C26	10.1 (4)
C7—C6—C11—C10	−1.2 (4)	C22—C17—C18—C19	0.7 (4)
C7—C6—C11—N2	178.0 (2)	C26—C27—O29—C30	−174.5 (2)
C7—C8—C9—C10	−0.1 (5)	C27—C26—O25—C20	−176.6 (2)
C8—C9—C10—C11	0.5 (4)	C31—C30—O29—C27	−79.9 (3)
C8—C9—C10—O12	−178.4 (3)	C32—C30—O29—C27	157.7 (3)
C9—C10—C11—C6	0.1 (4)	N2—C3—C4—C5	−0.4 (5)
C9—C10—C11—N2	−179.1 (2)	O12—C10—C11—C6	179.1 (2)
C9—C10—O12—Pt1	174.3 (2)	O12—C10—C11—N2	−0.1 (4)
C10—C11—N2—C3	−179.5 (2)	O23—C19—C20—C21	179.1 (3)
C10—C11—N2—Pt1	4.7 (3)	O23—C19—C20—O25	0.5 (4)
C11—C6—C7—C8	1.6 (4)	O25—C20—C21—C22	179.0 (3)
C11—C10—O12—Pt1	−4.7 (3)	O25—C26—C27—O28	10.2 (4)
C14—C15—C16—C17	156.2 (3)	O25—C26—C27—O29	−172.3 (2)
C15—C16—C17—C18	−92.4 (3)	O28—C27—O29—C30	3.0 (4)
C15—C16—C17—C22	86.9 (3)	Pt1—C14—C15—C16	−104.3 (3)
C16—C17—C18—C19	−180.0 (3)	Pt1—C15—C16—C17	76.6 (3)
C16—C17—C22—C21	179.4 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of ring N2/C3–C6/C11, Cg2 is the centroid of ring C6–C11 and Cg3 is the centroid of ring C17–C22.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O23ⁱ	0.95	2.46	3.073 (4)	122
C16—H16A···O12	0.99	2.40	3.051 (4)	123
C14—H14B···Cg1ⁱⁱ	0.99	2.94	3.454 (4)	114
C24—H24B···Cg2	0.98	2.93	3.564 (4)	124
C30—H30···Cg3ⁱⁱⁱ	1.00	2.96	3.827 (4)	145

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x−1, −y, −z+1; (iii) −x+1, −y, −z+1.

[η²-4-Allyl-2-methoxy-1-(propoxycarbonylmethoxy)benzene]chlorido(quinolin-2-carboxylato-κ²N,O)platinum(II) (chi33) top

Crystal data top

[Pt(C₁₀H₆O₂)Cl(C₁₅H₂₀O₄)]	F(000) = 1304
M_r = 667.01	D_x = 1.879 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 15.6457 (13) Å	Cell parameters from 6260 reflections
b = 9.7291 (4) Å	θ = 3.4–28.0°
c = 16.6062 (8) Å	µ = 6.11 mm⁻¹
β = 111.150 (8)°	T = 100 K
V = 2357.5 (3) Å³	Needle, yellow
Z = 4	0.3 × 0.15 × 0.10 mm

Data collection top

Agilent SuperNova Dual Source diffractometer with an Eos detector	4030 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	3348 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.066
Detector resolution: 15.9631 pixels mm^-1	θ_max = 24.7°, θ_min = 2.8°
ω scans	h = −18→18
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	k = −11→11
T_min = 0.522, T_max = 1.000	l = −19→19
21714 measured reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.038	H-atom parameters constrained
wR(F²) = 0.086	w = 1/[σ²(F_o²) + (0.0209P)² + 13.4203P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max = 0.001
4030 reflections	Δρ_max = 2.22 e Å⁻³
316 parameters	Δρ_min = −1.13 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Pt1A	0.69372 (3)	0.90310 (4)	0.69364 (2)	0.02742 (15)	0.9298 (13)
Pt1B	0.6573 (5)	0.9379 (6)	0.7023 (3)	0.02742 (15)	0.0702 (13)
Cl2A	0.74945 (19)	1.1196 (2)	0.69048 (14)	0.0519 (7)	0.9298 (13)
Cl2B	0.710 (3)	1.143 (4)	0.711 (2)	0.0519 (7)	0.0702 (13)
N3	0.6096 (4)	0.8677 (6)	0.5632 (3)	0.0261 (13)
C4	0.5626 (5)	0.7531 (7)	0.5569 (4)	0.0281 (16)
C5	0.5000 (5)	0.7022 (8)	0.4798 (4)	0.0380 (18)
H5	0.466660	0.620352	0.479342	0.046*
C6	0.4873 (6)	0.7711 (9)	0.4056 (5)	0.045 (2)
H6	0.444434	0.738369	0.352463	0.054*
C7	0.5374 (5)	0.8902 (8)	0.4075 (5)	0.0399 (19)
C8	0.5288 (6)	0.9618 (9)	0.3313 (5)	0.049 (2)
H8	0.486090	0.930261	0.277779	0.058*
C9	0.5800 (6)	1.0743 (10)	0.3325 (5)	0.052 (2)
H9	0.573686	1.121077	0.280497	0.063*
C10	0.6428 (6)	1.1212 (8)	0.4123 (5)	0.048 (2)
H10	0.678626	1.200557	0.413662	0.058*
C11	0.6532 (6)	1.0544 (8)	0.4881 (5)	0.0403 (19)
H11	0.696339	1.087252	0.541004	0.048*
C12	0.6004 (5)	0.9381 (7)	0.4874 (4)	0.0302 (16)
C13	0.5797 (5)	0.6706 (8)	0.6392 (4)	0.0326 (17)
O14	0.6441 (4)	0.7167 (5)	0.7062 (3)	0.0403 (13)
O15	0.5356 (4)	0.5679 (5)	0.6383 (3)	0.0402 (13)
C16	0.8065 (5)	0.8737 (8)	0.8114 (4)	0.0360 (18)
H16A	0.820957	0.779283	0.823459	0.043*
H16B	0.839552	0.927213	0.784616	0.043*
C17	0.7365 (5)	0.9339 (8)	0.8331 (4)	0.041 (2)
H17	0.747581	1.031930	0.852165	0.049*	0.9298 (13)
H17A	0.752705	1.027924	0.858348	0.049*	0.0702 (13)
C18	0.6843 (6)	0.8543 (9)	0.8744 (5)	0.047 (2)
H18A	0.688324	0.755037	0.863072	0.057*
H18B	0.618940	0.881693	0.850753	0.057*
C19	0.7245 (5)	0.8821 (9)	0.9717 (4)	0.041 (2)
C20	0.7935 (5)	0.7966 (8)	1.0248 (4)	0.0373 (18)
H20	0.814797	0.721662	1.000530	0.045*
C21	0.8313 (5)	0.8211 (8)	1.1136 (4)	0.0323 (17)
C22	0.7985 (5)	0.9311 (7)	1.1495 (4)	0.0304 (17)
C23	0.7315 (5)	1.0157 (8)	1.0962 (4)	0.0358 (17)
H23	0.710572	1.092086	1.119598	0.043*
C24	0.6942 (5)	0.9891 (8)	1.0073 (4)	0.0396 (19)
H24	0.646899	1.046700	0.971174	0.047*
O25	0.8981 (3)	0.7447 (5)	1.1711 (3)	0.0414 (13)
C26	0.9278 (6)	0.6241 (9)	1.1385 (5)	0.054 (2)
H26A	0.949783	0.650355	1.092396	0.081*
H26B	0.876367	0.560041	1.115666	0.081*
H26C	0.977560	0.579745	1.185385	0.081*
O27	0.8385 (3)	0.9431 (5)	1.2376 (3)	0.0336 (12)
C28	0.8073 (5)	1.0523 (7)	1.2750 (4)	0.0345 (18)
H28A	0.739919	1.046870	1.258444	0.041*
H28B	0.822518	1.141173	1.254417	0.041*
C29	0.8532 (5)	1.0422 (8)	1.3717 (4)	0.0305 (16)
O30	0.8787 (4)	0.9389 (5)	1.4110 (3)	0.0367 (12)
O31	0.8578 (3)	1.1679 (5)	1.4060 (3)	0.0366 (12)
C32	0.8972 (5)	1.1747 (8)	1.4997 (4)	0.0414 (19)
H32A	0.952958	1.116983	1.521270	0.050*
H32B	0.852620	1.139311	1.524470	0.050*
C33	0.9208 (6)	1.3209 (8)	1.5269 (5)	0.050 (2)
H33A	0.866320	1.380139	1.500989	0.060*
H33B	0.969642	1.353675	1.506787	0.060*
C34	0.9536 (7)	1.3289 (11)	1.6247 (5)	0.066 (3)
H34A	0.972162	1.423355	1.643341	0.099*
H34B	1.005973	1.267105	1.649891	0.099*
H34C	0.903806	1.301305	1.643904	0.099*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pt1A	0.0359 (3)	0.0302 (2)	0.01614 (15)	0.00021 (17)	0.00946 (13)	0.00123 (13)
Pt1B	0.0359 (3)	0.0302 (2)	0.01614 (15)	0.00021 (17)	0.00946 (13)	0.00123 (13)
Cl2A	0.0799 (19)	0.0368 (13)	0.0309 (12)	−0.0187 (12)	0.0103 (11)	0.0034 (9)
Cl2B	0.0799 (19)	0.0368 (13)	0.0309 (12)	−0.0187 (12)	0.0103 (11)	0.0034 (9)
N3	0.030 (3)	0.034 (4)	0.017 (3)	0.006 (3)	0.012 (2)	0.001 (2)
C4	0.031 (4)	0.036 (4)	0.020 (3)	0.004 (3)	0.011 (3)	0.001 (3)
C5	0.039 (4)	0.053 (5)	0.021 (4)	−0.007 (4)	0.010 (3)	−0.009 (3)
C6	0.057 (5)	0.055 (6)	0.022 (4)	0.008 (4)	0.012 (4)	−0.004 (4)
C7	0.051 (5)	0.052 (5)	0.025 (4)	0.018 (4)	0.023 (4)	0.002 (3)
C8	0.072 (6)	0.058 (6)	0.020 (4)	0.015 (5)	0.022 (4)	0.009 (4)
C9	0.072 (6)	0.067 (6)	0.028 (4)	0.031 (5)	0.030 (4)	0.016 (4)
C10	0.061 (6)	0.042 (5)	0.053 (5)	0.010 (4)	0.033 (5)	0.019 (4)
C11	0.054 (5)	0.043 (5)	0.028 (4)	0.010 (4)	0.020 (4)	0.007 (3)
C12	0.036 (4)	0.038 (4)	0.021 (4)	0.010 (3)	0.015 (3)	0.006 (3)
C13	0.037 (4)	0.041 (5)	0.022 (4)	0.000 (4)	0.013 (3)	0.002 (3)
O14	0.064 (4)	0.041 (3)	0.013 (2)	−0.013 (3)	0.010 (2)	0.004 (2)
O15	0.051 (3)	0.048 (3)	0.025 (3)	−0.022 (3)	0.018 (2)	−0.005 (2)
C16	0.043 (4)	0.041 (5)	0.022 (4)	0.004 (4)	0.009 (3)	0.004 (3)
C17	0.056 (5)	0.049 (5)	0.010 (3)	0.003 (4)	0.003 (3)	−0.002 (3)
C18	0.050 (5)	0.062 (6)	0.030 (4)	−0.013 (4)	0.016 (4)	−0.008 (4)
C19	0.047 (5)	0.059 (6)	0.019 (4)	−0.013 (4)	0.015 (4)	0.002 (4)
C20	0.048 (5)	0.042 (5)	0.031 (4)	−0.013 (4)	0.026 (4)	−0.013 (3)
C21	0.034 (4)	0.038 (4)	0.029 (4)	−0.005 (3)	0.015 (3)	−0.003 (3)
C22	0.037 (4)	0.037 (4)	0.019 (3)	−0.012 (3)	0.013 (3)	0.000 (3)
C23	0.040 (4)	0.042 (5)	0.026 (4)	−0.001 (4)	0.013 (3)	0.003 (3)
C24	0.041 (5)	0.055 (5)	0.020 (4)	−0.005 (4)	0.009 (3)	−0.001 (3)
O25	0.049 (3)	0.048 (3)	0.030 (3)	0.005 (3)	0.017 (3)	−0.009 (2)
C26	0.066 (6)	0.054 (6)	0.046 (5)	0.011 (5)	0.027 (5)	−0.009 (4)
O27	0.041 (3)	0.036 (3)	0.022 (2)	0.001 (2)	0.009 (2)	−0.005 (2)
C28	0.052 (5)	0.033 (4)	0.016 (3)	0.000 (3)	0.009 (3)	−0.001 (3)
C29	0.035 (4)	0.030 (4)	0.031 (4)	−0.002 (3)	0.017 (3)	−0.003 (3)
O30	0.053 (3)	0.032 (3)	0.023 (3)	0.000 (2)	0.011 (2)	−0.001 (2)
O31	0.056 (3)	0.030 (3)	0.020 (2)	0.003 (2)	0.010 (2)	−0.003 (2)
C32	0.048 (5)	0.053 (5)	0.022 (4)	0.003 (4)	0.012 (4)	−0.004 (3)
C33	0.067 (6)	0.045 (5)	0.032 (4)	0.012 (4)	0.008 (4)	−0.018 (4)
C34	0.067 (7)	0.085 (7)	0.039 (5)	0.011 (5)	0.011 (5)	−0.023 (5)

Geometric parameters (Å, º) top

PT1Aa—Cl2A	2.287 (2)	C17—C18	1.464 (11)
PT1Bb—Cl2B	2.14 (3)	C18—H18A	0.9900
PT1Aa—N3	2.118 (5)	C18—H18B	0.9900
PT1Bb—N3	2.262 (7)	C18—C19	1.533 (10)
PT1Aa—O14	2.013 (5)	C19—C20	1.396 (11)
PT1Bb—O14	2.166 (7)	C19—C24	1.363 (11)
PT1Bb—C16	2.464 (9)	C20—H20	0.9500
PT1Aa—C16	2.128 (7)	C20—C21	1.397 (9)
PT1Aa—C17	2.186 (6)	C21—C22	1.409 (10)
PT1Bb—C17	2.077 (8)	C21—O25	1.355 (8)
N3—C4	1.320 (9)	C22—C23	1.374 (10)
N3—C12	1.393 (8)	C22—O27	1.373 (7)
C4—C5	1.392 (9)	C23—H23	0.9500
C4—C13	1.522 (9)	C23—C24	1.402 (9)
C5—H5	0.9500	C24—H24	0.9500
C5—C6	1.353 (10)	O25—C26	1.437 (9)
C6—H6	0.9500	C26—H26A	0.9800
C6—C7	1.393 (11)	C26—H26B	0.9800
C7—C8	1.408 (10)	C26—H26C	0.9800
C7—C12	1.416 (10)	O27—C28	1.405 (8)
C8—H8	0.9500	C28—H28A	0.9900
C8—C9	1.352 (12)	C28—H28B	0.9900
C9—H9	0.9500	C28—C29	1.508 (9)
C9—C10	1.411 (12)	C29—O30	1.186 (8)
C10—H10	0.9500	C29—O31	1.340 (8)
C10—C11	1.372 (10)	O31—C32	1.453 (8)
C11—H11	0.9500	C32—H32A	0.9900
C11—C12	1.399 (10)	C32—H32B	0.9900
C13—O14	1.283 (8)	C32—C33	1.498 (11)
C13—O15	1.212 (8)	C33—H33A	0.9900
C16—H16A	0.9500	C33—H33B	0.9900
C16—H16B	0.9500	C33—C34	1.518 (10)
C16—C17	1.399 (10)	C34—H34A	0.9800
C17—H17	1.0000	C34—H34B	0.9800
C17—H17A	1.0000	C34—H34C	0.9800

CL2Bb—PT1Bb—N3	108.9 (9)	C17—PT1Bb—N3	156.2 (5)
CL2Bb—PT1Bb—O14	163.9 (12)	C17—PT1Bb—O14	88.7 (3)
CL2Bb—PT1Bb—C16	87.0 (10)	C17—PT1Bb—C16	34.6 (3)
PT1Aa—C16—H16A	112.3	C18—C17—Pt1A	114.5 (5)
PT1Aa—C16—H16B	84.7	C18—C17—Pt1B	106.1 (5)
H16Aa—C16—H16B	120.0	C18—C17—H17	114.7
PT1Aa—C17—H17	114.7	C18—C17—H17A	112.8
PT1Bb—C17—H17A	112.8	C17—C18—H18A	110.0
N3—PT1Aa—Cl2A	103.13 (16)	C17—C18—H18B	110.0
N3—PT1Bb—C16	123.4 (4)	C17—C18—C19	108.3 (6)
N3—PT1Aa—C16	157.1 (2)	H18A—C18—H18B	108.4
N3—PT1Aa—C17	161.0 (3)	C19—C18—H18A	110.0
C4—N3—Pt1A	109.9 (4)	C19—C18—H18B	110.0
C4—N3—Pt1B	107.7 (4)	C20—C19—C18	119.4 (7)
C4—N3—C12	118.1 (6)	C24—C19—C18	121.2 (7)
C12—N3—Pt1A	131.9 (5)	C24—C19—C20	119.5 (7)
C12—N3—Pt1B	131.5 (5)	C19—C20—H20	120.0
N3—C4—C5	124.0 (6)	C19—C20—C21	120.1 (7)
N3—C4—C13	117.5 (6)	C21—C20—H20	120.0
C5—C4—C13	118.4 (7)	C20—C21—C22	119.7 (7)
C4—C5—H5	120.5	O25—C21—C20	125.1 (7)
C6—C5—C4	119.0 (8)	O25—C21—C22	115.2 (6)
C6—C5—H5	120.5	C23—C22—C21	119.5 (6)
C5—C6—H6	120.2	O27—C22—C21	114.8 (6)
C5—C6—C7	119.6 (7)	O27—C22—C23	125.7 (7)
C7—C6—H6	120.2	C22—C23—H23	120.1
C6—C7—C8	121.4 (8)	C22—C23—C24	119.9 (7)
C6—C7—C12	119.4 (7)	C24—C23—H23	120.1
C8—C7—C12	119.2 (8)	C19—C24—C23	121.3 (7)
C7—C8—H8	119.2	C19—C24—H24	119.3
C9—C8—C7	121.5 (8)	C23—C24—H24	119.3
C9—C8—H8	119.2	C21—O25—C26	117.1 (6)
C8—C9—H9	120.5	O25—C26—H26A	109.5
C8—C9—C10	118.9 (7)	O25—C26—H26B	109.5
C10—C9—H9	120.5	O25—C26—H26C	109.5
C9—C10—H10	119.3	H26A—C26—H26B	109.5
C11—C10—C9	121.3 (8)	H26A—C26—H26C	109.5
C11—C10—H10	119.3	H26B—C26—H26C	109.5
C10—C11—H11	119.9	C22—O27—C28	115.9 (5)
C10—C11—C12	120.1 (8)	O27—C28—H28A	110.0
C12—C11—H11	119.9	O27—C28—H28B	110.0
N3—C12—C7	119.6 (7)	O27—C28—C29	108.3 (6)
N3—C12—C11	121.5 (6)	H28A—C28—H28B	108.4
C11—C12—C7	118.8 (6)	C29—C28—H28A	110.0
O14—C13—C4	115.1 (6)	C29—C28—H28B	110.0
O15—C13—C4	120.6 (6)	O30—C29—C28	125.3 (7)
O15—C13—O14	124.3 (6)	O30—C29—O31	125.7 (6)
C13—O14—Pt1A	115.8 (4)	O31—C29—C28	109.0 (6)
C13—O14—Pt1B	112.0 (5)	C29—O31—C32	115.7 (6)
C17—C16—Pt1A	73.4 (4)	O31—C32—H32A	109.8
O14—PT1Aa—Cl2A	175.13 (14)	O31—C32—H32B	109.8
O14—PT1Aa—N3	80.8 (2)	O31—C32—C33	109.2 (6)
O14—PT1Bb—N3	74.4 (2)	H32A—C32—H32B	108.3
O14—PT1Aa—C16	90.4 (2)	C33—C32—H32A	109.8
O14—PT1Bb—C16	78.5 (3)	C33—C32—H32B	109.8
O14—PT1Aa—C17	89.8 (3)	C32—C33—H33A	109.9
C16—PT1Aa—Cl2A	87.0 (2)	C32—C33—H33B	109.9
C16—PT1Aa—C17	37.8 (3)	C32—C33—C34	108.8 (7)
C17—C16—Pt1B	57.4 (4)	H33A—C33—H33B	108.3
C17—C16—H16A	120.0	C34—C33—H33A	109.9
C17—C16—H16B	120.0	C34—C33—H33B	109.9
C16—C17—Pt1A	68.8 (4)	C33—C34—H34A	109.5
C16—C17—Pt1B	88.0 (5)	C33—C34—H34B	109.5
C16—C17—H17	114.7	C33—C34—H34C	109.5
C16—C17—H17A	112.8	H34A—C34—H34B	109.5
C16—C17—C18	121.3 (7)	H34A—C34—H34C	109.5
C17—PT1Aa—Cl2A	85.7 (2)	H34B—C34—H34C	109.5
C17—PT1Bb—Cl2B	83.1 (9)

PT1Aa—N3—C4—C5	179.0 (6)	O15—C13—O14—PT1Bb	−150.9 (7)
PT1Bb—N3—C4—C5	159.5 (6)	O15—C13—O14—PT1Aa	−171.7 (6)
PT1Aa—N3—C4—C13	−2.3 (7)	PT1Aa—C16—C17—C18	106.5 (7)
PT1Bb—N3—C4—C13	−21.8 (7)	PT1Bb—C16—C17—C18	107.7 (7)
PT1Bb—N3—C12—C7	−155.0 (6)	PT1Aa—C17—C18—C19	177.7 (5)
PT1Aa—N3—C12—C7	−180.0 (5)	PT1Bb—C17—C18—C19	−163.8 (6)
PT1Bb—N3—C12—C11	26.1 (10)	C16—C17—C18—C19	98.5 (8)
PT1Aa—N3—C12—C11	1.2 (10)	C17—C18—C19—C20	−91.5 (9)
N3—C4—C5—C6	1.8 (11)	C17—C18—C19—C24	88.3 (9)
N3—C4—C13—O14	−4.9 (9)	C18—C19—C20—C21	179.6 (6)
N3—C4—C13—O15	176.6 (6)	C18—C19—C24—C23	−179.3 (7)
C4—N3—C12—C7	3.8 (9)	C19—C20—C21—C22	1.0 (10)
C4—N3—C12—C11	−175.0 (6)	C19—C20—C21—O25	179.7 (7)
C4—C5—C6—C7	0.6 (11)	C20—C19—C24—C23	0.5 (11)
C4—C13—O14—PT1Bb	30.8 (8)	C20—C21—C22—C23	−2.1 (10)
C4—C13—O14—PT1Aa	10.0 (8)	C20—C21—C22—O27	178.1 (6)
C5—C4—C13—O14	173.9 (6)	C20—C21—O25—C26	−4.3 (10)
C5—C4—C13—O15	−4.6 (10)	C21—C22—C23—C24	2.3 (11)
C5—C6—C7—C8	177.5 (7)	C21—C22—O27—C28	179.7 (6)
C5—C6—C7—C12	−0.6 (11)	C22—C21—O25—C26	174.5 (6)
C6—C7—C8—C9	−177.4 (8)	C22—C23—C24—C19	−1.6 (11)
C6—C7—C12—N3	−1.7 (10)	C22—O27—C28—C29	175.6 (6)
C6—C7—C12—C11	177.3 (7)	C23—C22—O27—C28	−0.1 (10)
C7—C8—C9—C10	−0.5 (12)	C24—C19—C20—C21	−0.2 (11)
C8—C7—C12—N3	−179.8 (6)	O25—C21—C22—C23	179.1 (6)
C8—C7—C12—C11	−0.9 (10)	O25—C21—C22—O27	−0.7 (9)
C8—C9—C10—C11	0.4 (12)	O27—C22—C23—C24	−177.9 (6)
C9—C10—C11—C12	−0.6 (12)	O27—C28—C29—O30	−28.6 (10)
C10—C11—C12—N3	179.7 (7)	O27—C28—C29—O31	153.3 (6)
C10—C11—C12—C7	0.8 (11)	C28—C29—O31—C32	177.5 (6)
C12—N3—C4—C5	−4.0 (10)	C29—O31—C32—C33	164.9 (7)
C12—N3—C4—C13	174.7 (6)	O30—C29—O31—C32	−0.5 (10)
C12—C7—C8—C9	0.7 (12)	O31—C32—C33—C34	174.8 (7)
C13—C4—C5—C6	−176.9 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···Cl2A	0.95	2.34	3.211 (8)	153
C11—H11···Cl2B	0.95	2.81	3.59 (3)	140
C16—H16A···O30ⁱ	0.95	2.55	3.452 (9)	159
C20—H20···O30ⁱ	0.95	2.59	3.524 (9)	167
C28—H28B···Cl2Aⁱⁱ	0.99	2.64	3.473 (7)	142
C32—H32A···O30ⁱⁱⁱ	0.99	2.52	3.459 (10)	158

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x, −y+5/2, z+1/2; (iii) −x+2, −y+2, −z+3.

Cations and anions detected by ESI mass spectroscopy (m/z, %) for complexes (2)–(6) and several other platinum(II) complexes top

Complexes	[M – Cl]⁺	[M + H]⁺	[M – H]^-	[M – AlkEug + Cl]^-	[2(M–Qui–HCl) + Cl]^-
[PtCl₂(PrEug)(Qui)] (2)	-	-	-	-	1022 (100)
[PtCl₂(ⁱPrEug)(Qui)] (3)	-	-	-	-	1022 (100)
[PtCl(Qui-O)(PrEug)] (4)	603 (100)	640 (50)	637 (45)	409 (40)	-
[PtCl(Qui-O)(ⁱPrEug)] (5)	603 (100)	640 (35)	637 (100)	409 (75)	-
[PtCl(Qui-COO)(PrEug)] (6)	631 (100)	667 (25)	666 (10)	438 (25)	-
[PtCl(Qui-O)(Eug)]^a	503 (100)	540 (25)	-	-	-
[PtCl(MeQui-O)(Eug)]^b	517 (100)	553 (10)	-	-	-
[PtCl(NO₂Qui-O)(Eug)]^b	548 (100)	584 (80)	-	-	-
[PtCl(ClQui-O)(Eug)]^b	571 (100)	607 (20)	-	-	-

References: (a) Chi et al. (2017a); (b) Chi et al. (2017b).

Chemical shift (ppm), multiplicity and coupling constant J_Pt-H (Hz) of H8, H9, H10, H12 and H18 in free AlkEug and in (1)–(6)^a top

Compound	H8a	H8b	H9	H10trans	H10cis	H12	H18
Free PrEug	3.32 d		5.96 m	5.06 dd	5.01 dd
Free ⁱPrEug	3.32 d		5.96 m	5.08–5.00 ov
(1a)^b	2.98 dd	3.49 dd	5.05 m	4.30 dd	4.13 ov
			²J_Pt-H 70	²J_Pt-H 70
(1b)^c	2.87 dd	3.48 dd	5.00 m	4.27 dd	4.10 dd
			²J_Pt-H 70	²J_Pt-H 70	²J_Pt-H 70
(2)	3.31 dd	3.61 dd	5.91 m	4.83 dd	4.72 dd	9.03 d	8.82 br
			²J_Pt-H 70	²J_Pt-H 70	²J_Pt-H 70
(3)	3.31 dd	3.61 dd	5.91 m	4.83 dd	4.72 dd	9.02 d	8.82 br
	³J_Pt-H 50		²J_Pt-H 70	²J_Pt-H 70	²J_Pt-H 70
(4)^d	3.27 dd	3.59 dd	5.59 m	4.76 d	4.73 d	9.07 d
	³J_Pt-H 50		²J_Pt-H 70	²J_Pt-H 70	²J_Pt-H 70	³J_Pt-H 34
(5)	3.27 dd	3.60 dd	5.61 m	4.76 d	4.74 d	9.07 d
	³J_Pt-H 50		²J_Pt-H 70	²J_Pt-H 70	²J_Pt-H 70	³J_Pt-H 34
(6)^e	3.22 br	3.57 br	5.90 m	4.88–4.91 ov	4.88–4.91 ov		9.58 d
			²J_Pt-H 70

Notes/references: (a) acetone-d₆; (b) Chi et al. (2013); (c) Thong & Chi (2014); (d) Chi et al. (2014); (e) chloroform-d₁.

Cytotoxic effects of the examined compounds (IC₅₀^a in µM) and some reference compounds top

Compound	KB	LU	Hep-G2	MCF-7
trans-[PtCl₂(Preug)(Qui)] (2)	4.27±0.09	7.02±0.28	6.64±0.20	6.47±0.32
trans-[PtCl₂(ⁱPreug)(Qui)] (3)	5.09±0.18	4.64±0.12	5.96±0.30	5.93±0.12
[PtCl(Qui-O)(Preug)] (4)	0.39±0.02	1.25±0.05	1.99±0.10	1.55±0.06
[PtCl(Qui-O)(ⁱPreug)] (5)	0.41±0.01	0.44±0.02	0.38±0.01	0.61±0.03
[PtCl(Qui-COO)(Preug)] (6)	7.27±0.32	18.60±0.37	14.68±0.45	29.23±1.24
Ellipcitine	1.26±0.03	1.42±0.07	2.15±0.09	1.83±0.06
[PtCl(Qui-O)(olefin)]^b	0.43-1.39	2.95-8.17	5.29–9.58	1.84–9.04
Other Pt^II	5.98-22.54^c		3.4–85.37^d	4.65–90.79^e
Qui-OH^f	37.89	62.96	43.54	40.37
Cisplatin^g	15.2	42.9	13.3	45.7

Notes: (a) IC₅₀ is the concentration of the compound required to inhibit cell growth by 50%. Mean values of IC₅₀ (in µM) ±S.D. from three experiments are presented. References: (b) Chi et al. (2017a) and Da et al. (2015); (c) Li et al. (2013); (d) Qin et al. (2015), Liu et al. (2014), Fang et al. (2016) and Meng et al. (2016); (e) Nakatake et al. (2011), Liu et al. (2014) and Abu-Safieh et al. (2016); (f) Da et al. (2015); (g) Chi et al. (2017a).

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Mixed natural aryl­olefin–quinoline platinum(II) complexes: synthesis, structural characterization and in vitro cytotoxicity studies

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Mixed natural arylolefin–quinoline platinum(II) complexes: synthesis, structural characterization and in vitro cytotoxicity studies