Synthesis, structure and in vitro cytotoxicity of platinum(II) complexes containing eugenol and a quinolin-8-ol-derived chelator

The synthesis of potassium (η²-4-allyl-2-meth­oxy­phenol)tri­chlorido­platin­ate(II), K[PtCl₃(C₁₀H₁₂O₂)], (1), starting from Zeise's salt and Ocimum sanctum L. oil has been optimized. Starting from (1), three new platinum(II) complexes, namely (η²-4-allyl-2-meth­oxy­phenol)chlorido­(2-methyl­quinolin-8-olato-κ²N,O)platinum(II), (2), (η²-4-allyl-2-meth­oxy­phenol)chlorido­(5-nitro­quinolin-8-olato-κ²N,O)platinum(II), (3), and (η²-4-allyl-2-meth­oxy­phenol)chlorido­(5,7-di­chloro­quinolin-8-olato-κ²N,O)platinum(II), [Pt(C₉H₄Cl₂NO)Cl(C₁₀H₁₂O₂)], (4), con­taining eugenol and a quinolin-8-ol derivative (R-OQ), have been synthesized and characterized by elemental analyses, MS, IR, ¹H NMR and NOESY spectra. For (1) and (4), single-crystal X-ray diffraction studies were also carried out. Complexes (2)–(4) show good inhibiting abilities on three human cancer cell lines, i.e. KB, Hep-G2 and LU, with IC₅₀ values of 1.42–17.8 µM. Complex (3) gives an impressively high activity against KB, Hep-G2, LU and MCF-7, with IC₅₀ values of 1.42–4.91 µM, which are much lower than those of cisplatin and some other platinum(II) complexes.

Computing details

For both structures, data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); 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).

Potassium [2-methoxy-4-(prop-2-en-1-yl)phenol]trichloridoplatinate (chi46-bis)

Crystal data

K[PtCl3(C10H12O2)]	F(000) = 944
Mr = 504.74	Dx = 2.230 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.0312 (6) Å	Cell parameters from 7771 reflections
b = 16.1528 (8) Å	θ = 2.9–28.9°
c = 8.1007 (4) Å	µ = 10.13 mm^−1
β = 107.295 (6)°	T = 100 K
V = 1503.09 (14) Å^3	Block, orange
Z = 4	0.4 × 0.4 × 0.3 mm

Data collection

Agilent SuperNova Single Source diffractometer with an Eos detector	3068 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source	2937 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.040
Detector resolution: 15.9631 pixels mm^-1	θmax = 26.4°, θmin = 2.5°
ω scans	h = −15→15
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	k = −20→20
Tmin = 0.548, Tmax = 1.000	l = −10→10
15723 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.023	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.042	w = 1/[σ^2(Fo^2) + (0.0018P)^2 + 2.9267P] where P = (Fo^2 + 2Fc^2)/3
S = 1.20	(Δ/σ)max = 0.001
3068 reflections	Δρmax = 0.84 e Å^−3
223 parameters	Δρmin = −0.92 e Å^−3
86 restraints

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Pt1	0.03063 (2)	0.61876 (2)	0.61000 (2)	0.01116 (5)
Cl2	0.00007 (9)	0.52042 (7)	0.79589 (13)	0.0170 (2)
Cl3	0.05273 (9)	0.71258 (7)	0.40833 (13)	0.0170 (2)
Cl4	−0.16013 (8)	0.66642 (7)	0.57359 (13)	0.0157 (2)
C5	0.1855 (3)	0.5583 (3)	0.5979 (6)	0.0182 (10)
H5AA	0.190091	0.502123	0.634271	0.022*	0.660 (7)
H5AB	0.159096	0.571387	0.478275	0.022*	0.660 (7)
H5BC	0.208644	0.576818	0.501798	0.022*	0.340 (7)
H5BD	0.143483	0.507948	0.590767	0.022*	0.340 (7)
C6A	0.2179 (7)	0.6218 (7)	0.7211 (12)	0.019 (2)	0.660 (7)
H6A	0.255879	0.670123	0.682536	0.022*	0.660 (7)
C6B	0.2138 (13)	0.6057 (12)	0.752 (2)	0.024 (6)	0.340 (7)
H6B	0.229669	0.572319	0.860608	0.029*	0.340 (7)
C7A	0.2599 (5)	0.6066 (5)	0.9099 (8)	0.0218 (17)	0.660 (7)
H7AA	0.241063	0.549019	0.933938	0.026*	0.660 (7)
H7AB	0.219363	0.644363	0.969129	0.026*	0.660 (7)
C7B	0.2795 (9)	0.6850 (9)	0.7706 (17)	0.021 (3)	0.340 (7)
H7BA	0.241636	0.727150	0.824511	0.026*	0.340 (7)
H7BB	0.278844	0.705422	0.655138	0.026*	0.340 (7)
C8A	0.3914 (5)	0.6201 (5)	0.9814 (9)	0.0191 (17)	0.660 (7)
C8B	0.4047 (10)	0.6719 (9)	0.8824 (17)	0.022 (3)	0.340 (7)
C9A	0.4377 (6)	0.6569 (5)	1.1405 (10)	0.0260 (19)	0.660 (7)
H9A	0.388045	0.677607	1.202752	0.031*	0.660 (7)
C9B	0.4420 (10)	0.7014 (10)	1.0501 (19)	0.025 (4)	0.340 (7)
H9B	0.387507	0.729390	1.094352	0.030*	0.340 (7)
C10A	0.5587 (7)	0.6635 (7)	1.2095 (12)	0.027 (2)	0.660 (7)
H10A	0.594 (9)	0.693 (7)	1.326 (12)	0.032*	0.660 (7)
C10B	0.5561 (12)	0.6919 (10)	1.158 (2)	0.021 (4)	0.340 (7)
H10B	0.580 (17)	0.708 (13)	1.28 (3)	0.025*	0.340 (7)
C11	0.6324 (4)	0.6398 (3)	1.1107 (6)	0.0258 (11)
C12	0.5895 (4)	0.6071 (4)	0.9453 (7)	0.0385 (15)
C13A	0.4661 (6)	0.5932 (5)	0.8894 (10)	0.0225 (18)	0.660 (7)
H13A	0.433527	0.564059	0.784180	0.027*	0.660 (7)
C13B	0.4833 (11)	0.6285 (10)	0.816 (2)	0.019 (3)	0.340 (7)
H13B	0.451 (11)	0.620 (8)	0.676 (18)	0.023*	0.340 (7)
O14	0.6714 (3)	0.5793 (2)	0.8717 (4)	0.0346 (9)
C15	0.6306 (5)	0.5409 (4)	0.7064 (7)	0.0557 (19)
H15A	0.586848	0.490800	0.715270	0.084*
H15B	0.697057	0.526185	0.665823	0.084*
H15C	0.579774	0.579406	0.624329	0.084*
O16	0.7498 (3)	0.6391 (2)	1.1804 (4)	0.0234 (8)
K17	−0.09497 (8)	0.64632 (6)	1.00825 (12)	0.0173 (2)
H16	0.763 (4)	0.653 (3)	1.271 (6)	0.019 (15)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pt1	0.01111 (8)	0.01302 (10)	0.00792 (9)	0.00074 (7)	0.00064 (6)	−0.00023 (7)
Cl2	0.0220 (5)	0.0151 (6)	0.0135 (5)	0.0025 (4)	0.0048 (4)	0.0051 (4)
Cl3	0.0189 (5)	0.0183 (6)	0.0140 (5)	0.0008 (4)	0.0055 (4)	0.0046 (4)
Cl4	0.0118 (5)	0.0198 (6)	0.0140 (5)	0.0019 (4)	0.0015 (4)	−0.0004 (4)
C5	0.012 (2)	0.023 (3)	0.016 (2)	0.0063 (18)	−0.0003 (17)	0.0012 (19)
C6A	0.010 (5)	0.026 (5)	0.018 (4)	0.002 (4)	0.001 (3)	0.000 (3)
C6B	0.006 (8)	0.028 (9)	0.033 (10)	0.004 (6)	−0.001 (7)	−0.013 (8)
C7A	0.016 (3)	0.034 (5)	0.014 (3)	−0.003 (3)	0.002 (3)	−0.007 (3)
C7B	0.012 (5)	0.031 (7)	0.018 (7)	0.003 (5)	0.000 (5)	−0.006 (6)
C8A	0.013 (3)	0.027 (4)	0.014 (3)	−0.001 (3)	0.000 (2)	−0.001 (3)
C8B	0.008 (5)	0.032 (9)	0.021 (6)	−0.003 (5)	0.000 (4)	−0.005 (6)
C9A	0.015 (3)	0.042 (5)	0.018 (4)	0.003 (3)	0.001 (3)	−0.010 (4)
C9B	0.015 (5)	0.037 (10)	0.022 (6)	0.009 (6)	0.004 (5)	−0.007 (6)
C10A	0.016 (3)	0.033 (7)	0.024 (5)	0.001 (4)	−0.004 (3)	−0.007 (4)
C10B	0.023 (6)	0.014 (9)	0.019 (8)	0.005 (6)	−0.004 (5)	0.003 (6)
C11	0.013 (2)	0.029 (3)	0.030 (3)	−0.001 (2)	−0.0027 (19)	−0.008 (2)
C12	0.016 (2)	0.045 (4)	0.044 (3)	0.009 (2)	−0.006 (2)	−0.026 (3)
C13A	0.018 (4)	0.032 (5)	0.015 (4)	0.001 (3)	0.001 (3)	−0.005 (4)
C13B	0.013 (7)	0.026 (9)	0.019 (8)	0.001 (6)	0.004 (6)	0.000 (7)
O14	0.0207 (17)	0.052 (3)	0.026 (2)	−0.0032 (17)	−0.0019 (15)	−0.0183 (18)
C15	0.041 (3)	0.084 (5)	0.038 (4)	−0.015 (3)	0.005 (3)	−0.038 (4)
O16	0.0127 (16)	0.043 (2)	0.0118 (18)	−0.0013 (15)	−0.0005 (14)	−0.0029 (17)
K17	0.0186 (5)	0.0157 (5)	0.0187 (5)	0.0007 (4)	0.0071 (4)	0.0009 (4)

Geometric parameters (Å, º)

Pt1—Cl2	2.2924 (10)	Cl2—K17	3.0940 (14)
Pt1—Cl3	2.3010 (10)	Cl2—K17^ii	3.1619 (14)
Pt1—Cl4	2.3547 (10)	Cl3—K17^i	3.1405 (14)
Pt1—C5	2.132 (4)	Cl3—K17^iii	3.3738 (14)
Pt1—C6A	2.164 (8)	Cl4—K17^i	3.2078 (14)
C6A—H6A	1.0000	Cl4—K17	3.3878 (14)
Pt1—C6B	2.172 (14)	C5—H5AA	0.9500
C6B—H6B	1.0000	C5—H5AB	0.9500
C6A—C7A	1.482 (11)	C5—H5BC	0.9500
C7A—H7AA	0.9900	C5—H5BD	0.9500
C7A—H7AB	0.9900	C5—C6A	1.404 (9)
C6B—C7B	1.490 (17)	C5—C6B	1.417 (14)
C7B—H7BA	0.9900	C11—C12	1.389 (7)
C7B—H7BB	0.9900	C11—O16	1.356 (5)
C7A—C8A	1.529 (8)	C12—C13A	1.435 (8)
C7B—C8B	1.524 (13)	C12—C13B	1.433 (15)
C8A—C9A	1.378 (9)	C12—O14	1.371 (6)
C9A—H9A	0.9500	O14—C15	1.424 (6)
C8B—C9B	1.382 (18)	O14—K17^iv	2.906 (3)
C9B—H9B	0.9500	C15—H15A	0.9800
C9A—C10A	1.400 (9)	C15—H15B	0.9800
C10A—H10A	1.02 (12)	C15—H15C	0.9800
C9B—C10B	1.399 (13)	O16—K17^iv	2.645 (3)
C10B—H10B	1.0 (2)	O16—H16	0.74 (4)
C10A—C11	1.412 (8)	K17—Pt1^v	4.0769 (10)
C10B—C11	1.380 (12)	K17—Cl2^ii	3.1619 (14)
C8A—C13A	1.397 (9)	K17—Cl3^vi	3.3738 (14)
C13A—H13A	0.9500	K17—Cl3^v	3.1404 (14)
C8B—C13B	1.407 (18)	K17—Cl4^v	3.2078 (14)
C13B—H13B	1.09 (13)	K17—O14^vii	2.906 (3)
Pt1—K17^i	4.0769 (10)	K17—O16^vii	2.645 (3)
Pt1—K17	3.9734 (9)
Cl2—Pt1—Cl3	176.11 (4)	C6B—C5—H5BC	120.0
Cl2—Pt1—Cl4	88.18 (4)	H5BC—C5—H5BD	120.0
Cl2—Pt1—K17^i	130.96 (3)	C6B—C5—H5BD	120.0
C7A—C6A—Pt1	114.8 (6)	C10B—C11—C12	114.3 (8)
C7B—C6B—Pt1	113.2 (12)	C12—C11—C10A	122.3 (5)
C6B—Pt1—Cl2	85.4 (6)	O16—C11—C10A	121.2 (5)
C6A—Pt1—Cl2	95.3 (3)	O16—C11—C10B	125.9 (8)
C6B—Pt1—Cl3	97.3 (6)	O16—C11—C12	116.1 (4)
C6A—Pt1—Cl3	87.4 (3)	C11—C12—C13A	114.7 (5)
C6A—Pt1—Cl4	154.2 (2)	C11—C12—C13B	127.5 (7)
C6B—Pt1—Cl4	153.6 (4)	O14—C12—C11	115.8 (4)
C7A—C6A—H6A	113.9	O14—C12—C13A	128.4 (5)
Pt1—C6A—H6A	113.9	O14—C12—C13B	111.1 (7)
Pt1—C6B—H6B	114.7	C12—O14—C15	117.4 (4)
C7B—C6B—H6B	114.7	C12—O14—K17^iv	116.8 (3)
C9A—C8A—C7A	120.1 (6)	C15—O14—K17^iv	123.0 (3)
Cl2—Pt1—K17	50.98 (3)	O14—C15—H15A	109.5
Cl3—Pt1—Cl4	90.56 (4)	O14—C15—H15B	109.5
Cl3—Pt1—K17	130.90 (3)	O14—C15—H15C	109.5
Cl3—Pt1—K17^i	50.03 (3)	H15A—C15—H15B	109.5
Cl4—Pt1—K17	58.22 (3)	H15A—C15—H15C	109.5
Cl4—Pt1—K17^i	51.79 (3)	H15B—C15—H15C	109.5
C5—Pt1—Cl2	91.46 (13)	C11—O16—K17^iv	126.3 (3)
C5—Pt1—Cl3	88.98 (13)	C11—O16—H16	107 (4)
C5—Pt1—Cl4	167.63 (12)	K17^iv—O16—H16	123 (4)
C5—Pt1—C6A	38.1 (3)	Pt1—K17—Pt1^v	93.488 (19)
C5—Pt1—C6B	38.4 (4)	Cl2—K17—Pt1	35.14 (2)
C5—Pt1—K17	129.58 (12)	Cl2—K17—Pt1^v	123.24 (3)
C13A—C8A—C7A	120.7 (6)	Cl2^ii—K17—Pt1	98.29 (3)
C6A—C7A—H7AA	109.4	Cl2^ii—K17—Pt1^v	129.38 (3)
C8A—C7A—H7AA	109.4	Cl2—K17—Cl2^ii	65.23 (4)
C6A—C7A—H7AB	109.4	Cl2—K17—Cl3^v	90.16 (3)
C8A—C7A—H7AB	109.4	Cl2^ii—K17—Cl3^vi	77.27 (3)
H7AA—C7A—H7AB	108.0	Cl2—K17—Cl3^vi	124.50 (4)
C13B—C8B—C7B	120.0 (12)	Cl2^ii—K17—Cl4^v	142.17 (4)
C9B—C8B—C7B	120.7 (11)	Cl2^ii—K17—Cl4	122.73 (4)
C8B—C7B—H7BA	109.7	Cl2—K17—Cl4^v	149.36 (4)
C5—Pt1—K17^i	133.93 (13)	Cl2—K17—Cl4	59.65 (3)
K17—Pt1—K17^i	81.506 (18)	Cl3^vi—K17—Pt1^v	56.83 (2)
Pt1—Cl2—K17	93.88 (4)	Cl3^v—K17—Pt1^v	34.16 (2)
Pt1—Cl2—K17^ii	144.62 (4)	Cl3^vi—K17—Pt1	126.63 (3)
K17—Cl2—K17^ii	114.77 (4)	Cl3^v—K17—Pt1	59.41 (2)
Pt1—Cl3—K17^iii	109.52 (4)	Cl3^v—K17—Cl2^ii	126.86 (4)
Pt1—Cl3—K17^i	95.81 (4)	Cl3^v—K17—Cl3^vi	80.83 (3)
K17^i—Cl3—K17^iii	107.52 (4)	Cl3^v—K17—Cl4^v	62.81 (3)
Pt1—Cl4—K17^i	92.98 (4)	Cl3^v—K17—Cl4	68.68 (3)
Pt1—Cl4—K17	85.57 (3)	Cl3^vi—K17—Cl4	149.44 (4)
K17^i—Cl4—K17	105.63 (4)	Cl4—K17—Pt1^v	94.49 (3)
Pt1—C5—H5AA	113.2	Cl4^v—K17—Pt1	114.22 (3)
Pt1—C5—H5AB	85.0	Cl4—K17—Pt1	36.216 (19)
Pt1—C5—H5BC	111.5	Cl4^v—K17—Pt1^v	35.23 (2)
Pt1—C5—H5BD	86.5	Cl4^v—K17—Cl3^vi	68.11 (3)
C6B—C7B—H7BA	109.7	Cl4^v—K17—Cl4	95.09 (3)
C6B—C7B—H7BB	109.7	C5—C6B—Pt1	69.3 (5)
H7BA—C7B—H7BB	108.2	C5—C6A—Pt1	69.7 (3)
C8B—C7B—H7BB	109.7	O14^vii—K17—Pt1	101.97 (7)
C6A—C7A—C8A	111.4 (6)	C5—C6A—H6A	113.9
C6B—C7B—C8B	110.0 (11)	O14^vii—K17—Pt1^v	133.01 (8)
C10A—C9A—H9A	120.3	O14^vii—K17—Cl2^ii	92.16 (8)
C8A—C9A—H9A	120.3	O14^vii—K17—Cl2	91.08 (7)
C8B—C9B—H9B	118.4	O14^vii—K17—Cl3^v	136.85 (8)
C10B—C9B—H9B	118.4	O14^vii—K17—Cl3^vi	131.10 (7)
C8A—C9A—C10A	119.4 (7)	O14^vii—K17—Cl4	75.01 (7)
C9A—C10A—H10A	120 (6)	C5—C6B—H6B	114.7
C8B—C9B—C10B	123.1 (12)	C5—C6A—C7A	123.3 (9)
C9B—C10B—H10B	122 (10)	C5—C6B—C7B	122.3 (17)
C9A—C10A—C11	120.4 (7)	C11—C10B—C9B	120.4 (13)
C8A—C13A—C12	123.5 (6)	C11—C10A—H10A	119 (6)
C8B—C13B—C12	113.2 (12)	C11—C10B—H10B	115 (10)
C9A—C8A—C13A	119.2 (6)	C12—C13A—H13A	118.2
C8A—C13A—H13A	118.2	C12—C13B—H13B	134 (7)
C9B—C8B—C13B	119.3 (11)	O14^vii—K17—Cl4^v	99.09 (8)
C8B—C13B—H13B	113 (7)	O16^vii—K17—Pt1	157.17 (8)
C6A—Pt1—K17	105.1 (3)	O16^vii—K17—Pt1^v	102.25 (8)
C6B—Pt1—K17	98.7 (5)	O16^vii—K17—Cl2	134.40 (9)
C6B—Pt1—K17^i	117.0 (5)	O16^vii—K17—Cl2^ii	84.49 (8)
C6A—Pt1—K17^i	109.9 (3)	O16^vii—K17—Cl3^v	135.28 (9)
C6B—C5—Pt1	72.3 (7)	O16^vii—K17—Cl3^vi	76.15 (8)
C6A—C5—Pt1	72.1 (4)	O16^vii—K17—Cl4	124.80 (8)
C6A—C5—H5AA	120.0	O16^vii—K17—Cl4^v	73.10 (9)
H5AA—C5—H5AB	120.0	O16^vii—K17—O14^vii	55.21 (10)
C6A—C5—H5AB	120.0
Pt1—C6A—C7A—C8A	−173.1 (5)	C9B—C8B—C13B—C12	11 (2)
C10B—C11—C12—O14	158.7 (9)	C7A—C8A—C13A—C12	177.2 (7)
C7A—C8A—C9A—C10A	175.5 (8)	C9B—C10B—C11—C12	6.5 (18)
C10A—C11—C12—O14	−173.7 (7)	C9A—C10A—C11—C12	−2.0 (13)
C13A—C12—O14—C15	9.3 (10)	C9B—C10B—C11—O16	164.0 (11)
Pt1—C6B—C7B—C8B	175.9 (9)	C9A—C10A—C11—O16	−174.3 (7)
C13B—C12—O14—C15	−27.8 (10)	Pt1—C5—C6B—C7B	−105.0 (14)
C13A—C8A—C9A—C10A	−2.5 (12)	Pt1—C5—C6A—C7A	107.0 (8)
C13B—C8B—C9B—C10B	2 (2)	O16—C11—C12—C13A	167.8 (6)
C13A—C12—O14—K17^iv	171.0 (6)	O16—C11—C12—C13B	−152.2 (9)
C13B—C12—O14—K17^iv	133.9 (7)	C10B—C11—C12—C13B	7.6 (14)
C10A—C11—O16—K17^iv	−158.4 (6)	C10A—C11—C12—C13A	−4.8 (10)
C10B—C11—O16—K17^iv	−128.2 (10)	C5—C6A—C7A—C8A	105.7 (9)
C6A—C7A—C8A—C9A	141.5 (8)	C5—C6B—C7B—C8B	−104.7 (15)
C7B—C8B—C9B—C10B	−179.3 (14)	C11—C12—C13B—C8B	−16.3 (17)
C6B—C7B—C8B—C9B	−106.4 (17)	C11—C12—C13A—C8A	8.3 (11)
C6A—C7A—C8A—C13A	−40.6 (10)	C11—C12—O14—C15	176.4 (5)
C6B—C7B—C8B—C13B	72.7 (17)	C11—C12—O14—K17^iv	−21.9 (7)
C8B—C9B—C10B—C11	−11 (2)	C12—C11—O16—K17^iv	28.9 (6)
C8A—C9A—C10A—C11	5.9 (13)	O14—C12—C13B—C8B	−168.5 (10)
C9A—C8A—C13A—C12	−4.8 (13)	O14—C12—C13A—C8A	175.6 (7)
C7B—C8B—C13B—C12	−168.3 (11)	O16—C11—C12—O14	−1.1 (8)

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

Chlorido(5,7-dichloroquinolin-8-olato-κ²N,O)[η²-2-methoxy4-(prop-2-en-1-yl)phenol]platinum(II) (chi47)

Crystal data

[Pt(C9H4Cl2NO)Cl(C10H12O2)]	Z = 2
Mr = 607.77	F(000) = 580
Triclinic, P1	Dx = 2.105 Mg m^−3
a = 8.1313 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.2960 (5) Å	Cell parameters from 8641 reflections
c = 11.4294 (7) Å	θ = 2.7–28.7°
α = 88.793 (4)°	µ = 7.75 mm^−1
β = 76.567 (4)°	T = 100 K
γ = 70.219 (4)°	Block, red
V = 958.93 (8) Å^3	0.4 × 0.4 × 0.3 mm

Data collection

Agilent SuperNova Single Source diffractometer with an Eos detector	3916 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source	3594 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.075
Detector resolution: 15.9631 pixels mm^-1	θmax = 26.4°, θmin = 2.6°
ω scans	h = −10→10
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)'	k = −14→14
Tmin = 0.427, Tmax = 1.000	l = −14→14
19518 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.036	H-atom parameters constrained
wR(F^2) = 0.088	w = 1/[σ^2(Fo^2) + (0.0357P)^2 + 3.4074P] where P = (Fo^2 + 2Fc^2)/3
S = 1.11	(Δ/σ)max = 0.001
3916 reflections	Δρmax = 2.51 e Å^−3
301 parameters	Δρmin = −1.82 e Å^−3
133 restraints

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Pt1	0.14705 (3)	0.96032 (2)	0.26050 (2)	0.02811 (10)
Cl2	0.0222 (2)	1.11888 (15)	0.14588 (16)	0.0345 (3)
N3	0.1551 (6)	1.0774 (5)	0.3907 (5)	0.0262 (11)
C4	0.1051 (9)	1.2027 (6)	0.3969 (6)	0.0330 (14)
H4	0.047134	1.248354	0.338451	0.040*
C5	0.1352 (10)	1.2685 (6)	0.4864 (7)	0.0400 (17)
H5	0.100651	1.357709	0.487104	0.048*
C6	0.2139 (9)	1.2058 (6)	0.5728 (6)	0.0355 (15)
H6	0.235347	1.251198	0.633300	0.043*
C7	0.2646 (8)	1.0718 (6)	0.5730 (6)	0.0308 (14)
C8	0.2319 (8)	1.0114 (6)	0.4770 (6)	0.0281 (13)
C9	0.3429 (8)	0.9951 (6)	0.6578 (6)	0.0310 (14)
C10	0.3859 (8)	0.8670 (7)	0.6481 (6)	0.0374 (16)
H10	0.438456	0.816484	0.706339	0.045*
C11	0.3528 (9)	0.8103 (6)	0.5528 (7)	0.0366 (15)
C12	0.2794 (8)	0.8787 (6)	0.4643 (6)	0.0321 (14)
Cl13	0.3868 (2)	1.06459 (19)	0.77586 (17)	0.0451 (4)
Cl14	0.4066 (3)	0.64855 (16)	0.5444 (2)	0.0515 (5)
O15	0.2484 (6)	0.8261 (4)	0.3718 (4)	0.0293 (10)
C16	0.0992 (8)	0.8260 (5)	0.1543 (6)	0.0275 (13)
H16A	0.028415	0.865219	0.099486	0.033*	0.642 (14)
H16B	0.044563	0.800448	0.228535	0.033*	0.642 (14)
H16C	0.119883	0.751658	0.197415	0.033*	0.358 (14)
H16D	−0.020384	0.880995	0.158895	0.033*	0.358 (14)
C17A	0.2824 (11)	0.8061 (9)	0.1258 (9)	0.023 (2)	0.642 (14)
H17A	0.359776	0.726697	0.153591	0.027*	0.642 (14)
C18A	0.3650 (13)	0.8478 (8)	0.0073 (8)	0.026 (2)	0.642 (14)
H18A	0.441328	0.895982	0.020389	0.031*	0.642 (14)
H18B	0.268854	0.903299	−0.028744	0.031*	0.642 (14)
C17B	0.248 (2)	0.8553 (18)	0.0823 (17)	0.032 (4)	0.358 (14)
H17B	0.221031	0.907729	0.012979	0.038*	0.358 (14)
C18B	0.443 (2)	0.7762 (17)	0.0675 (16)	0.033 (5)	0.358 (14)
H18C	0.456357	0.725518	0.138688	0.039*	0.358 (14)
H18D	0.514423	0.832591	0.064764	0.039*	0.358 (14)
C19A	0.4779 (13)	0.7327 (10)	−0.0775 (9)	0.022 (2)	0.642 (14)
C19B	0.520 (2)	0.6883 (18)	−0.0453 (15)	0.023 (4)	0.358 (14)
C20A	0.3996 (19)	0.6476 (11)	−0.1080 (11)	0.033 (3)	0.642 (14)
H20A	0.274710	0.664134	−0.075862	0.040*	0.642 (14)
C20B	0.419 (3)	0.6252 (17)	−0.0844 (17)	0.050 (9)	0.358 (14)
H20B	0.297018	0.640626	−0.043390	0.060*	0.358 (14)
C21	0.4993 (8)	0.5401 (6)	−0.1837 (6)	0.0299 (13)
C22	0.6812 (8)	0.5156 (6)	−0.2377 (6)	0.0293 (13)
C23A	0.762 (4)	0.600 (2)	−0.203 (2)	0.033 (4)	0.642 (14)
H23A	0.886790	0.583737	−0.234774	0.040*	0.642 (14)
C23B	0.775 (8)	0.576 (4)	−0.208 (4)	0.033 (8)	0.358 (14)
H23B	0.894799	0.561564	−0.252360	0.039*	0.358 (14)
C24A	0.6623 (15)	0.7057 (13)	−0.1242 (14)	0.026 (3)	0.642 (14)
H24A	0.719814	0.759358	−0.102246	0.031*	0.642 (14)
C24B	0.698 (3)	0.664 (2)	−0.110 (3)	0.031 (6)	0.358 (14)
H24B	0.767578	0.707108	−0.085722	0.037*	0.358 (14)
O25	0.4277 (6)	0.4582 (4)	−0.2227 (4)	0.0329 (10)
C26	0.2421 (10)	0.4809 (8)	−0.1717 (9)	0.058 (3)
H26A	0.203159	0.421892	−0.210399	0.087*
H26B	0.171820	0.567540	−0.184504	0.087*
H26C	0.223374	0.468880	−0.085070	0.087*
O27	0.7760 (6)	0.4213 (4)	−0.3243 (5)	0.0380 (11)
H27	0.711748	0.379066	−0.332794	0.057*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pt1	0.01719 (13)	0.03008 (14)	0.03482 (17)	−0.00513 (9)	−0.00551 (10)	−0.00864 (10)
Cl2	0.0328 (8)	0.0408 (8)	0.0348 (9)	−0.0167 (7)	−0.0116 (7)	0.0031 (7)
N3	0.016 (2)	0.034 (3)	0.024 (3)	−0.002 (2)	−0.002 (2)	−0.006 (2)
C4	0.027 (3)	0.030 (3)	0.037 (4)	−0.007 (3)	0.000 (3)	−0.004 (3)
C5	0.036 (4)	0.035 (3)	0.043 (4)	−0.007 (3)	−0.003 (3)	−0.014 (3)
C6	0.035 (4)	0.041 (4)	0.027 (4)	−0.014 (3)	0.005 (3)	−0.018 (3)
C7	0.016 (3)	0.042 (3)	0.028 (3)	−0.006 (3)	0.002 (2)	−0.008 (3)
C8	0.014 (3)	0.034 (3)	0.030 (3)	−0.006 (2)	0.004 (2)	−0.008 (3)
C9	0.019 (3)	0.046 (4)	0.030 (4)	−0.013 (3)	−0.006 (3)	−0.005 (3)
C10	0.016 (3)	0.057 (4)	0.037 (4)	−0.008 (3)	−0.007 (3)	0.002 (3)
C11	0.024 (3)	0.034 (3)	0.047 (4)	−0.005 (3)	−0.007 (3)	−0.002 (3)
C12	0.016 (3)	0.038 (3)	0.040 (4)	−0.007 (2)	−0.004 (3)	−0.006 (3)
Cl13	0.0286 (8)	0.0715 (12)	0.0349 (10)	−0.0157 (8)	−0.0075 (7)	−0.0130 (8)
Cl14	0.0568 (12)	0.0340 (9)	0.0632 (13)	−0.0055 (8)	−0.0288 (10)	0.0048 (8)
O15	0.022 (2)	0.028 (2)	0.039 (3)	−0.0065 (17)	−0.0110 (19)	−0.0055 (18)
C16	0.020 (3)	0.027 (3)	0.033 (3)	−0.003 (2)	−0.009 (2)	−0.009 (2)
C17A	0.017 (4)	0.026 (5)	0.021 (5)	−0.001 (3)	−0.008 (3)	0.001 (4)
C18A	0.031 (5)	0.025 (4)	0.025 (5)	−0.012 (4)	−0.010 (4)	0.003 (3)
C17B	0.025 (7)	0.043 (11)	0.033 (11)	−0.014 (6)	−0.011 (6)	−0.016 (8)
C18B	0.023 (7)	0.049 (10)	0.027 (9)	−0.014 (7)	−0.003 (6)	−0.012 (7)
C19A	0.021 (5)	0.030 (5)	0.017 (5)	−0.011 (4)	−0.004 (4)	0.004 (4)
C19B	0.024 (8)	0.030 (9)	0.014 (8)	−0.008 (6)	−0.010 (6)	0.004 (6)
C20A	0.019 (5)	0.043 (5)	0.038 (7)	−0.015 (4)	−0.001 (5)	−0.009 (4)
C20B	0.033 (11)	0.077 (17)	0.041 (12)	−0.030 (11)	0.007 (9)	−0.030 (12)
C21	0.024 (3)	0.038 (3)	0.027 (3)	−0.010 (2)	−0.006 (2)	−0.005 (2)
C22	0.024 (3)	0.032 (3)	0.028 (3)	−0.004 (2)	−0.007 (2)	0.005 (2)
C23A	0.020 (6)	0.037 (8)	0.038 (9)	−0.008 (6)	−0.001 (5)	0.003 (6)
C23B	0.025 (10)	0.034 (15)	0.032 (13)	−0.005 (10)	−0.003 (8)	−0.004 (10)
C24A	0.019 (5)	0.030 (7)	0.032 (6)	−0.012 (5)	−0.009 (4)	0.008 (5)
C24B	0.027 (9)	0.035 (14)	0.033 (11)	−0.013 (9)	−0.007 (8)	−0.001 (9)
O25	0.026 (2)	0.036 (2)	0.037 (3)	−0.0098 (19)	−0.008 (2)	−0.0086 (19)
C26	0.030 (4)	0.065 (5)	0.082 (7)	−0.025 (4)	−0.003 (4)	−0.032 (5)
O27	0.027 (2)	0.030 (2)	0.047 (3)	−0.0040 (19)	0.003 (2)	−0.004 (2)

Geometric parameters (Å, º)

Pt1—Cl2	2.2898 (17)	C4—H4	0.9500
Pt1—N3	2.038 (5)	C4—C5	1.389 (9)
Pt1—O15	2.039 (5)	C5—H5	0.9500
Pt1—C16	2.150 (5)	C5—C6	1.358 (10)
Pt1—C17A	2.155 (10)	C6—H6	0.9500
C17A—H17A	1.0000	C6—C7	1.428 (9)
C17A—C18A	1.507 (12)	C7—C8	1.425 (9)
C18A—H18A	0.9900	C7—C9	1.405 (10)
C18A—H18B	0.9900	C8—C12	1.417 (9)
Pt1—C17B	2.213 (18)	C9—C10	1.370 (10)
C17B—H17B	1.0000	C9—Cl13	1.737 (6)
C17B—C18B	1.506 (17)	C10—H10	0.9500
C18B—H18C	0.9900	C10—C11	1.397 (10)
C18B—H18D	0.9900	C11—C12	1.383 (10)
C18A—C19A	1.518 (11)	C11—Cl14	1.728 (7)
C18B—C19B	1.516 (16)	C12—O15	1.336 (8)
C19A—C20A	1.408 (11)	C16—H16A	0.9500
C20A—H20A	0.9500	C16—H16B	0.9500
C19B—C20B	1.402 (15)	C16—H16C	0.9500
C20B—H20B	0.9500	C16—H16D	0.9500
C20B—C21	1.384 (15)	C16—C17A	1.388 (10)
C20A—C21	1.390 (11)	C16—C17B	1.432 (16)
C23A—H23A	0.9500	C21—C22	1.397 (9)
C23B—H23B	0.9500	C21—O25	1.377 (7)
C19A—C24A	1.397 (11)	C22—C23A	1.44 (3)
C23A—C24A	1.393 (13)	C22—C23B	1.28 (5)
C24A—H24A	0.9500	C22—O27	1.357 (7)
C19B—C24B	1.398 (15)	O25—C26	1.420 (8)
C23B—C24B	1.388 (16)	C26—H26A	0.9800
C24B—H24B	0.9500	C26—H26B	0.9800
N3—C4	1.331 (8)	C26—H26C	0.9800
N3—C8	1.364 (8)	O27—H27	0.8400
C18A—C17A—Pt1	112.3 (6)	N3—C8—C12	115.8 (6)
C18B—C17B—Pt1	109.0 (12)	C12—C8—C7	122.1 (6)
C17A—Pt1—Cl2	100.9 (3)	C7—C9—Cl13	119.2 (5)
N3—Pt1—Cl2	95.07 (15)	C10—C9—C7	120.9 (6)
C17B—Pt1—Cl2	80.9 (6)	C10—C9—Cl13	119.9 (5)
N3—Pt1—O15	82.14 (19)	C9—C10—H10	119.9
C18A—C17A—H17A	115.7	C9—C10—C11	120.2 (7)
N3—Pt1—C16	167.6 (2)	C11—C10—H10	119.9
N3—Pt1—C17A	150.1 (3)	C10—C11—Cl14	118.9 (6)
Pt1—C17A—H17A	115.7	C12—C11—C10	122.5 (6)
C24A—C19A—C18A	121.5 (10)	C12—C11—Cl14	118.6 (5)
N3—Pt1—C17B	153.8 (4)	C11—C12—C8	116.6 (6)
C20A—C19A—C18A	120.4 (8)	O15—C12—C8	120.0 (6)
O15—Pt1—Cl2	176.45 (12)	O15—C12—C11	123.4 (6)
C19A—C18A—H18A	109.8	C12—O15—Pt1	110.4 (4)
O15—Pt1—C16	91.8 (2)	Pt1—C16—H16A	112.4
O15—Pt1—C17A	82.5 (3)	Pt1—C16—H16B	86.5
O15—Pt1—C17B	102.6 (6)	Pt1—C16—H16C	105.6
C17A—C18A—H18A	109.8	C23A—C24A—H24A	120.0
H18A—C18A—H18B	108.3	C19B—C24B—H24B	119.5
C19A—C18A—H18B	109.8	C23B—C24B—H24B	119.5
C16—Pt1—Cl2	90.53 (18)	C17A—C16—Pt1	71.4 (5)
C16—Pt1—C17A	37.6 (3)	C17B—C16—Pt1	73.2 (7)
C16—Pt1—C17B	38.3 (4)	C17A—C16—H16A	120.0
C4—N3—Pt1	129.0 (5)	C17A—C16—H16B	120.0
C17A—C18A—H18B	109.8	H16A—C16—H16B	120.0
C18B—C17B—H17B	114.8	C17B—C16—H16C	120.0
Pt1—C17B—H17B	114.8	C17B—C16—H16D	120.0
C24B—C19B—C18B	120.1 (18)	H16C—C16—H16D	120.0
C4—N3—C8	119.4 (5)	Pt1—C16—H16D	91.2
C8—N3—Pt1	111.5 (4)	C20B—C21—C22	118.7 (12)
C20B—C19B—C18B	121.4 (14)	O25—C21—C20A	124.5 (7)
C17B—C18B—H18C	108.9	O25—C21—C20B	125.8 (12)
N3—C4—H4	119.0	O25—C21—C22	114.4 (5)
N3—C4—C5	122.0 (7)	C20A—C21—C22	120.8 (8)
C5—C4—H4	119.0	C21—C22—C23A	116.8 (11)
C19B—C18B—H18C	108.9	C23B—C22—C21	123.7 (19)
H18C—C18B—H18D	107.8	C23B—C22—O27	114.1 (19)
C17B—C18B—H18D	108.9	C16—C17A—Pt1	71.0 (4)
C4—C5—H5	119.9	C16—C17B—Pt1	68.5 (7)
C6—C5—C4	120.3 (6)	C16—C17A—H17A	115.7
C6—C5—H5	119.9	C16—C17A—C18A	118.7 (8)
C5—C6—H6	119.9	C16—C17B—H17B	114.8
C5—C6—C7	120.2 (6)	C16—C17B—C18B	125.2 (17)
C7—C6—H6	119.9	C21—C20A—C19A	122.1 (11)
C8—C7—C6	116.0 (6)	C21—C20B—C19B	118.9 (18)
C9—C7—C6	126.4 (6)	C21—C20A—H20A	119.0
C9—C7—C8	117.6 (6)	C21—C20B—H20B	120.5
C19B—C18B—H18D	108.9	O27—C22—C21	122.2 (6)
C17A—C18A—C19A	109.3 (7)	O27—C22—C23A	120.8 (10)
C23A—C24A—C19A	120.1 (17)	C21—O25—C26	116.3 (5)
C23B—C24B—C19B	121 (3)	C22—C23A—H23A	119.0
C17B—C18B—C19B	113.2 (14)	C22—C23B—H23B	120.5
C24A—C19A—C20A	118.1 (11)	C22—C23B—C24B	119 (4)
C19A—C20A—H20A	119.0	O25—C26—H26A	109.5
C24B—C19B—C20B	118.4 (19)	O25—C26—H26B	109.5
C19B—C20B—H20B	120.5	O25—C26—H26C	109.5
C24A—C23A—C22	122 (2)	H26A—C26—H26B	109.5
C24A—C23A—H23A	119.0	H26A—C26—H26C	109.5
C24B—C23B—H23B	120.5	H26B—C26—H26C	109.5
C19A—C24A—H24A	120.0	C22—O27—H27	109.5
N3—C8—C7	122.1 (6)
Pt1—C17A—C18A—C19A	172.6 (6)	C6—C7—C9—C10	−179.9 (6)
Pt1—C17B—C18B—C19B	173.0 (13)	C6—C7—C9—Cl13	−0.3 (9)
C18A—C19A—C24A—C23A	−179.1 (18)	C7—C8—C12—C11	2.7 (9)
C20B—C19B—C24B—C23B	−2 (4)	C7—C8—C12—O15	−179.0 (5)
C17A—C18A—C19A—C24A	−119.8 (11)	C7—C9—C10—C11	0.2 (10)
C20A—C19A—C24A—C23A	3 (2)	C8—N3—C4—C5	2.6 (9)
C17A—C18A—C19A—C20A	58.2 (12)	C8—C7—C9—C10	0.0 (9)
C18B—C19B—C24B—C23B	175 (3)	C8—C7—C9—Cl13	179.6 (4)
C17B—C18B—C19B—C20B	−39 (2)	C8—C12—O15—Pt1	3.6 (7)
C17B—C18B—C19B—C24B	144.0 (19)	C9—C7—C8—N3	179.5 (5)
C18A—C19A—C20A—C21	−178.9 (11)	C9—C7—C8—C12	−1.5 (9)
C24B—C19B—C20B—C21	0.8 (18)	C9—C10—C11—C12	1.1 (10)
C18B—C19B—C20B—C21	−176.0 (19)	C9—C10—C11—Cl14	−179.3 (5)
C24A—C19A—C20A—C21	−0.9 (15)	C10—C11—C12—C8	−2.5 (10)
C19B—C20B—C21—C22	3.1 (17)	C10—C11—C12—O15	179.3 (6)
C19A—C20A—C21—C22	−3.3 (14)	C11—C12—O15—Pt1	−178.2 (5)
C19B—C20B—C21—O25	170.2 (11)	Cl13—C9—C10—C11	−179.4 (5)
C19A—C20A—C21—O25	−175.6 (9)	Cl14—C11—C12—C8	178.0 (5)
Pt1—N3—C4—C5	−173.6 (5)	Cl14—C11—C12—O15	−0.3 (9)
Pt1—N3—C8—C7	175.4 (4)	C20A—C21—C22—O27	−170.9 (8)
Pt1—N3—C8—C12	−3.7 (6)	C20B—C21—C22—O27	170.7 (11)
Pt1—C16—C17A—C18A	−105.6 (8)	O25—C21—C22—C23A	178.3 (16)
Pt1—C16—C17B—C18B	98.6 (16)	O25—C21—C22—C23B	−175 (3)
C20B—C21—C22—C23B	−7 (4)	C20B—C21—O25—C26	13.5 (14)
C20A—C21—C22—C23A	5 (2)	C20A—C21—O25—C26	−6.1 (11)
N3—C4—C5—C6	−1.6 (11)	C16—C17A—C18A—C19A	−107.5 (9)
N3—C8—C12—C11	−178.2 (6)	C16—C17B—C18B—C19B	96 (2)
N3—C8—C12—O15	0.1 (8)	C21—C22—C23A—C24A	−3 (3)
C4—N3—C8—C7	−1.5 (9)	C21—C22—C23B—C24B	6 (6)
C4—N3—C8—C12	179.4 (6)	C22—C23B—C24B—C19B	−2 (6)
C4—C5—C6—C7	−0.6 (10)	C22—C23A—C24A—C19A	−1 (3)
C5—C6—C7—C8	1.6 (9)	C22—C21—O25—C26	−178.9 (7)
C5—C6—C7—C9	−178.4 (6)	O25—C21—C22—O27	2.2 (9)
C6—C7—C8—N3	−0.6 (9)	O27—C22—C23A—C24A	172.9 (18)
C6—C7—C8—C12	178.4 (6)	O27—C22—C23B—C24B	−172 (3)