{4,5-Dimeth­oxy-2-[(2,3-η)-2-prop-2-en-1-yl]phenyl-κC1}(8-hy­droxy­quinolinato-κN,O)platinum(II)

Bui, T.Y.H.; Nguyen Thi Thanh, C.; Van Meervelt, L.

doi:10.1107/S2414314615024281

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 1| January 2016| x152428

doi:10.1107/S2414314615024281

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{4,5-Dimethoxy-2-[(2,3-η)-2-prop-2-en-1-yl]phenyl-κC¹}(8-hydroxyquinolinato-κN,O)platinum(II)

Thi Yen Hang Bui,^a Chi Nguyen Thi Thanh ^a and Luc Van Meervelt ^b ^*

^aChemistry Department, Hanoi National University of Education, 136 – Xuan Thuy – Cau Giay, Hanoi, Vietnam, and ^bChemistry Department, KU Leuven, Celestijnenlaan 200F, B-3001 Leuven (Heverlee), Belgium
^*Correspondence e-mail: luc.vanmeervelt@chem.kuleuven.be

Edited by M. Weil, Vienna University of Technology, Austria (Received 29 October 2015; accepted 17 December 2015; online 16 January 2016)

The crystal structure of the organoplatinum(II) title complex, [Pt(C₉H₆NO)(C₁₁H₁₃O₂)] or [Pt(methyleugenol)(8-hydroxyquinolinato)], has been determined in order to verify the coordination environment of the Pt^II cation, which was found to be square-planar with the N and O atoms of the quinolinate ligand cis and trans, respectively, with respect to the ethylenic double bond. The least-squares planes through the two aromatic ring systems make an angle of 39.87 (10)°. In the crystal, chains are formed parallel to [100] sustained by C—H⋯O hydrogen bonds. Parallel chains further interact via C—H⋯O and C—H⋯π contacts. The complex shows interesting activity on four human cancer cell lines with IC₅₀ values between 1.92 and 4.86 µM.

Keywords: crystal structure; platinum(II) complex; eugenol; 8-hydroxyquinoline; anticancer complex.

CCDC reference: 1443086

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Chemical scheme

Structure description

The title compound is shown in Fig. 1. Numerical details of the hydrogen-bonding interactions are given in Table 1 and the packing is shown in Fig. 2. For the synthesis and antitumor activity of organoplatinum(II) complexes containing aryl olefins and quinolines, see: Da et al. (2015b ). For similar structures of organoplatinum(II) complexes containing eugenol, see: Da et al. (2008 , 2015a ); Mangwala Kimpende et al. (2014 ).

Table 1
Hydrogen-bond geometry (Å, °)

Cg5 and Cg6 are the centroids of the N2–C11 and C6–C11 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O22ⁱ	0.95	2.39	3.330 (3)	169
C15—H15B⋯O12ⁱⁱ	0.99	2.51	3.425 (3)	153
C8—H8⋯Cg5ⁱⁱⁱ	0.95	2.82	3.389 (3)	119
C8—H8⋯Cg6ⁱⁱⁱ	0.95	2.89	3.745 (3)	150
Symmetry codes: (i) x-1, y, z; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Figure 1
Molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level.

Figure 2
Partial packing diagram showing C—H⋯O interactions (red dotted lines) and C—H⋯π interactions (blue dotted lines).

Synthesis and crystallization

The title compound was synthesized according to Da et al. (2015b) and recrystallized in acetone/water (5/1 v/v) to obtain brown crystals.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	[Pt(C₉H₆NO)(C₁₁H₁₃O₂)]
M_r	516.45
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	13.2250 (5), 15.0844 (6), 8.4294 (3)
β (°)	93.951 (3)
V (Å³)	1677.59 (11)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	8.38
Crystal size (mm)	0.2 × 0.1 × 0.1

Data collection
Diffractometer	Agilent SuperNova (single source at offset, Eos detector) diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2012 )
T_min, T_max	0.715, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	17650, 3429, 3106
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.015, 0.034, 1.05
No. of reflections	3429
No. of parameters	228
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.44
Computer programs: CrysAlis PRO (Agilent, 2012), SHELXS97 (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ), OLEX2 (Dolomanov et al., 2009 ).

Structural data

CCDC reference: 1443086

Crystal structure: contains datablock I. DOI: 10.1107/S2414314615024281/wm4002sup1.cif

Structure factors: contains datablock chi40. DOI: 10.1107/S2414314615024281/wm4002Isup2.hkl

checkCIF report

Synthesis and crystallization top

The title compound was synthesized according to Da et al. (2015b) and re-crystallized in acetone/water (5/1 v/v) to obtain brown crystals.

Refinement top

All H atoms were placed in idealized positions and refined in riding mode, with U_iso(H) values assigned as 1.2U_eq of the parent atoms (1.5 times for methyl groups) and with C—H distances of 0.95 (aromatic), 0.99 (CH₂), 1.00 (CH) or 0.98 Å (CH₃).

Related literature top

For the synthesis and antitumor activity of organoplatinum(II) complexes containing aryl olefins and quinolines, see: Da et al. (2015b). For similar structures of organoplatinum(II) complexes containing eugenol, see: Da et al. (2008); Mangwala Kimpende et al. (2014); Da et al. (2015a).

Experimental top

The title compound was synthesized according to Da et al. (2015b) and re-crystallized in acetone/water (5/1 v/v) to obtain brown crystals.

Structure description top

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); 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).

Figures top

	Fig. 1. Molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Partial packing diagram showing C—H···O interactions (red dotted lines) and C—H···π interactions (blue dotted lines).

{4,5-Dimethoxy-2-[(2,3-η)-2-prop-2-en-1-yl]phenyl-κC¹}(8-hydroxyquinolinato-κN,O)platinum(II) top

Crystal data top

[Pt(C₉H₆NO)(C₁₁H₁₃O₂)]	F(000) = 992
M_r = 516.45	D_x = 2.045 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.2250 (5) Å	Cell parameters from 9136 reflections
b = 15.0844 (6) Å	θ = 3.1–29.1°
c = 8.4294 (3) Å	µ = 8.38 mm⁻¹
β = 93.951 (3)°	T = 100 K
V = 1677.59 (11) Å³	Block, brown
Z = 4	0.2 × 0.1 × 0.1 mm

Data collection top

Agilent SuperNova (single source at offset, Eos detector) diffractometer	3429 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	3106 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.030
Detector resolution: 15.9631 pixels mm^-1	θ_max = 26.4°, θ_min = 2.7°
ω scans	h = −16→16
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −18→18
T_min = 0.715, T_max = 1.000	l = −10→10
17650 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)] = 0.015	H-atom parameters constrained
wR(F²) = 0.034	w = 1/[σ²(F_o²) + (0.0116P)² + 1.0756P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
3429 reflections	Δρ_max = 0.41 e Å⁻³
228 parameters	Δρ_min = −0.44 e Å⁻³
0 restraints

Crystal data top

[Pt(C₉H₆NO)(C₁₁H₁₃O₂)]	V = 1677.59 (11) Å³
M_r = 516.45	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.2250 (5) Å	µ = 8.38 mm⁻¹
b = 15.0844 (6) Å	T = 100 K
c = 8.4294 (3) Å	0.2 × 0.1 × 0.1 mm
β = 93.951 (3)°

Data collection top

Agilent SuperNova (single source at offset, Eos detector) diffractometer	3429 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	3106 reflections with I > 2σ(I)
T_min = 0.715, T_max = 1.000	R_int = 0.030
17650 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.015	0 restraints
wR(F²) = 0.034	H-atom parameters constrained
S = 1.05	Δρ_max = 0.41 e Å⁻³
3429 reflections	Δρ_min = −0.44 e Å⁻³
228 parameters

Special details top

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

Refinement. All H atoms were placed in idealized positions and refined in riding mode, with U_iso(H) values assigned as 1.2U_eq of the parent atoms (1.5 times for methyl groups) and with C—H distances of 0.95 (aromatic), 0.99 (CH₂), 1.00 (CH) or 0.98 Å (CH₃).

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

	x	y	z	U_iso*/U_eq
Pt1	0.12790 (2)	0.09931 (2)	0.17780 (2)	0.01039 (4)
O12	0.11032 (14)	0.14501 (12)	−0.0478 (2)	0.0135 (4)
O24	0.58770 (14)	0.16254 (13)	0.2776 (2)	0.0196 (4)
C25	0.6319 (2)	0.1692 (2)	0.4370 (3)	0.0202 (6)
H25A	0.7059	0.1712	0.4355	0.030*
H25B	0.6122	0.1176	0.4984	0.030*
H25C	0.6078	0.2234	0.4863	0.030*
C10	0.0132 (2)	0.15209 (17)	−0.0999 (3)	0.0132 (6)
N2	−0.02987 (17)	0.08111 (14)	0.1373 (3)	0.0127 (5)
C5	−0.2370 (2)	0.08998 (17)	0.0501 (3)	0.0176 (6)
H5	−0.3079	0.0932	0.0231	0.021*
C17	0.2759 (2)	0.12436 (17)	0.2018 (3)	0.0116 (5)
C14	0.1447 (2)	0.10721 (18)	0.4297 (3)	0.0155 (6)
H14	0.0826	0.1244	0.4836	0.019*
C21	0.4200 (2)	0.16086 (17)	0.3832 (3)	0.0147 (6)
H21	0.4465	0.1767	0.4869	0.018*
O22	0.51395 (14)	0.12214 (13)	−0.0056 (2)	0.0175 (4)
C15	0.2403 (2)	0.15860 (18)	0.4792 (3)	0.0156 (6)
H15A	0.2697	0.1365	0.5829	0.019*
H15B	0.2240	0.2222	0.4908	0.019*
C16	0.3160 (2)	0.14691 (17)	0.3533 (3)	0.0135 (6)
C23	0.4760 (2)	0.0986 (2)	−0.1624 (3)	0.0223 (7)
H23A	0.5325	0.0939	−0.2313	0.033*
H23B	0.4286	0.1442	−0.2041	0.033*
H23C	0.4409	0.0414	−0.1595	0.033*
C13	0.1492 (2)	0.01869 (18)	0.3798 (3)	0.0164 (6)
H13A	0.0915	−0.0197	0.4042	0.020*
H13B	0.2159	−0.0110	0.3963	0.020*
C6	−0.1675 (2)	0.12442 (17)	−0.0548 (3)	0.0146 (6)
C18	0.3412 (2)	0.11678 (17)	0.0781 (3)	0.0125 (6)
H18	0.3145	0.1026	−0.0263	0.015*
C20	0.4843 (2)	0.15159 (18)	0.2610 (3)	0.0154 (6)
C11	−0.0634 (2)	0.11804 (16)	−0.0059 (3)	0.0120 (6)
C8	−0.1220 (2)	0.19969 (18)	−0.2892 (3)	0.0200 (6)
H8	−0.1416	0.2278	−0.3874	0.024*
C7	−0.1953 (2)	0.16732 (18)	−0.1991 (3)	0.0197 (6)
H7	−0.2648	0.1737	−0.2337	0.024*
C3	−0.0977 (2)	0.04905 (18)	0.2309 (3)	0.0177 (6)
H3	−0.0747	0.0229	0.3294	0.021*
C19	0.4443 (2)	0.12990 (17)	0.1077 (3)	0.0129 (6)
C9	−0.0180 (2)	0.19275 (17)	−0.2414 (3)	0.0164 (6)
H9	0.0310	0.2163	−0.3072	0.020*
C4	−0.2018 (2)	0.05227 (18)	0.1900 (3)	0.0190 (6)
H4	−0.2480	0.0281	0.2597	0.023*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pt1	0.00723 (6)	0.01203 (6)	0.01194 (6)	0.00009 (4)	0.00097 (4)	0.00022 (4)
O12	0.0096 (9)	0.0165 (10)	0.0144 (10)	−0.0013 (8)	0.0002 (7)	0.0027 (8)
O24	0.0080 (10)	0.0366 (12)	0.0139 (10)	−0.0025 (9)	−0.0016 (8)	−0.0010 (9)
C25	0.0111 (14)	0.0314 (17)	0.0171 (15)	−0.0003 (12)	−0.0057 (11)	−0.0027 (13)
C10	0.0133 (14)	0.0099 (13)	0.0164 (14)	−0.0022 (11)	0.0003 (11)	−0.0037 (11)
N2	0.0110 (12)	0.0150 (12)	0.0121 (11)	−0.0016 (9)	0.0009 (9)	−0.0015 (9)
C5	0.0094 (14)	0.0155 (14)	0.0278 (16)	−0.0006 (11)	0.0004 (12)	−0.0071 (12)
C17	0.0085 (13)	0.0128 (13)	0.0132 (14)	0.0011 (11)	−0.0004 (10)	−0.0003 (11)
C14	0.0143 (14)	0.0225 (15)	0.0097 (14)	−0.0016 (12)	0.0016 (11)	0.0017 (11)
C21	0.0143 (14)	0.0183 (14)	0.0108 (14)	0.0006 (12)	−0.0035 (11)	−0.0021 (11)
O22	0.0099 (10)	0.0315 (11)	0.0113 (10)	−0.0018 (9)	0.0009 (8)	−0.0013 (8)
C15	0.0137 (14)	0.0183 (14)	0.0149 (14)	0.0015 (12)	0.0028 (11)	−0.0028 (12)
C16	0.0124 (14)	0.0149 (14)	0.0137 (14)	0.0020 (11)	0.0048 (11)	0.0005 (11)
C23	0.0178 (16)	0.0365 (18)	0.0129 (15)	−0.0030 (13)	0.0035 (12)	−0.0037 (13)
C13	0.0175 (15)	0.0193 (15)	0.0121 (14)	0.0004 (12)	−0.0002 (11)	0.0058 (11)
C6	0.0128 (14)	0.0093 (13)	0.0215 (15)	−0.0004 (11)	−0.0001 (11)	−0.0049 (11)
C18	0.0111 (14)	0.0145 (13)	0.0117 (14)	0.0005 (11)	−0.0009 (11)	0.0009 (11)
C20	0.0079 (14)	0.0184 (14)	0.0198 (15)	0.0001 (11)	0.0001 (11)	0.0006 (12)
C11	0.0115 (14)	0.0092 (13)	0.0151 (14)	0.0008 (10)	0.0001 (11)	−0.0035 (10)
C8	0.0258 (16)	0.0117 (13)	0.0210 (15)	0.0002 (12)	−0.0091 (12)	0.0034 (12)
C7	0.0154 (15)	0.0140 (14)	0.0289 (17)	0.0003 (12)	−0.0042 (12)	−0.0046 (12)
C3	0.0154 (15)	0.0178 (15)	0.0201 (15)	−0.0009 (12)	0.0025 (12)	−0.0028 (12)
C19	0.0130 (14)	0.0139 (13)	0.0121 (14)	0.0013 (11)	0.0023 (11)	0.0014 (11)
C9	0.0185 (15)	0.0118 (13)	0.0184 (14)	−0.0035 (12)	−0.0013 (11)	0.0002 (11)
C4	0.0111 (14)	0.0206 (15)	0.0260 (16)	−0.0017 (12)	0.0067 (12)	−0.0045 (13)

Geometric parameters (Å, º) top

Pt1—O12	2.0214 (17)	C21—C20	1.388 (4)
Pt1—N2	2.109 (2)	O22—C23	1.425 (3)
Pt1—C17	1.990 (3)	O22—C19	1.377 (3)
Pt1—C14	2.123 (3)	C15—H15A	0.9900
Pt1—C13	2.096 (3)	C15—H15B	0.9900
O12—C10	1.333 (3)	C15—C16	1.519 (3)
O24—C25	1.431 (3)	C23—H23A	0.9800
O24—C20	1.375 (3)	C23—H23B	0.9800
C25—H25A	0.9800	C23—H23C	0.9800
C25—H25B	0.9800	C13—H13A	0.9900
C25—H25C	0.9800	C13—H13B	0.9900
C10—C11	1.424 (4)	C6—C11	1.413 (4)
C10—C9	1.379 (4)	C6—C7	1.404 (4)
N2—C11	1.375 (3)	C18—H18	0.9500
N2—C3	1.327 (3)	C18—C19	1.383 (4)
C5—H5	0.9500	C20—C19	1.401 (4)
C5—C6	1.418 (4)	C8—H8	0.9500
C5—C4	1.362 (4)	C8—C7	1.362 (4)
C17—C16	1.391 (4)	C8—C9	1.411 (4)
C17—C18	1.403 (4)	C7—H7	0.9500
C14—H14	1.0000	C3—H3	0.9500
C14—C15	1.516 (4)	C3—C4	1.396 (4)
C14—C13	1.402 (4)	C9—H9	0.9500
C21—H21	0.9500	C4—H4	0.9500
C21—C16	1.396 (4)

O12—Pt1—N2	81.01 (8)	C17—C16—C21	120.7 (2)
O12—Pt1—C14	156.82 (9)	C17—C16—C15	116.2 (2)
O12—Pt1—C13	164.32 (9)	C21—C16—C15	123.0 (2)
N2—Pt1—C14	101.75 (9)	O22—C23—H23A	109.5
C17—Pt1—O12	94.56 (9)	O22—C23—H23B	109.5
C17—Pt1—N2	175.14 (9)	O22—C23—H23C	109.5
C17—Pt1—C14	81.55 (11)	H23A—C23—H23B	109.5
C17—Pt1—C13	87.21 (11)	H23A—C23—H23C	109.5
C13—Pt1—N2	97.60 (10)	H23B—C23—H23C	109.5
C13—Pt1—C14	38.82 (10)	Pt1—C13—H13A	116.4
C10—O12—Pt1	112.50 (15)	Pt1—C13—H13B	116.4
C20—O24—C25	116.3 (2)	C14—C13—Pt1	71.63 (15)
O24—C25—H25A	109.5	C14—C13—H13A	116.4
O24—C25—H25B	109.5	C14—C13—H13B	116.4
O24—C25—H25C	109.5	H13A—C13—H13B	113.4
H25A—C25—H25B	109.5	C11—C6—C5	117.0 (3)
H25A—C25—H25C	109.5	C7—C6—C5	124.6 (3)
H25B—C25—H25C	109.5	C7—C6—C11	118.4 (2)
O12—C10—C11	119.6 (2)	C17—C18—H18	119.9
O12—C10—C9	122.9 (2)	C19—C18—C17	120.2 (2)
C9—C10—C11	117.4 (3)	C19—C18—H18	119.9
C11—N2—Pt1	110.18 (16)	O24—C20—C21	124.7 (2)
C3—N2—Pt1	130.82 (19)	O24—C20—C19	115.6 (2)
C3—N2—C11	118.6 (2)	C21—C20—C19	119.7 (2)
C6—C5—H5	120.2	N2—C11—C10	115.9 (2)
C4—C5—H5	120.2	N2—C11—C6	122.2 (2)
C4—C5—C6	119.7 (3)	C6—C11—C10	122.0 (2)
C16—C17—Pt1	116.74 (19)	C7—C8—H8	118.9
C16—C17—C18	119.1 (2)	C7—C8—C9	122.1 (3)
C18—C17—Pt1	124.07 (19)	C9—C8—H8	118.9
Pt1—C14—H14	115.9	C6—C7—H7	120.2
C15—C14—Pt1	109.38 (17)	C8—C7—C6	119.6 (3)
C15—C14—H14	115.9	C8—C7—H7	120.2
C13—C14—Pt1	69.55 (15)	N2—C3—H3	118.8
C13—C14—H14	115.9	N2—C3—C4	122.4 (3)
C13—C14—C15	121.2 (2)	C4—C3—H3	118.8
C16—C21—H21	120.1	O22—C19—C18	124.1 (2)
C20—C21—H21	120.1	O22—C19—C20	115.5 (2)
C20—C21—C16	119.8 (2)	C18—C19—C20	120.3 (2)
C19—O22—C23	117.0 (2)	C10—C9—C8	120.5 (3)
C14—C15—H15A	109.9	C10—C9—H9	119.8
C14—C15—H15B	109.9	C8—C9—H9	119.8
C14—C15—C16	109.0 (2)	C5—C4—C3	120.1 (3)
H15A—C15—H15B	108.3	C5—C4—H4	120.0
C16—C15—H15A	109.9	C3—C4—H4	120.0
C16—C15—H15B	109.9

Pt1—O12—C10—C11	−7.8 (3)	C15—C14—C13—Pt1	−100.9 (2)
Pt1—O12—C10—C9	171.0 (2)	C16—C17—C18—C19	1.3 (4)
Pt1—N2—C11—C10	5.4 (3)	C16—C21—C20—O24	−179.1 (2)
Pt1—N2—C11—C6	−172.66 (19)	C16—C21—C20—C19	1.2 (4)
Pt1—N2—C3—C4	171.8 (2)	C23—O22—C19—C18	−0.4 (4)
Pt1—C17—C16—C21	176.5 (2)	C23—O22—C19—C20	178.9 (2)
Pt1—C17—C16—C15	−5.8 (3)	C13—C14—C15—C16	48.9 (3)
Pt1—C17—C18—C19	−175.8 (2)	C6—C5—C4—C3	1.2 (4)
Pt1—C14—C15—C16	−28.4 (3)	C18—C17—C16—C21	−0.8 (4)
O12—C10—C11—N2	1.4 (4)	C18—C17—C16—C15	176.9 (2)
O12—C10—C11—C6	179.5 (2)	C20—C21—C16—C17	−0.5 (4)
O12—C10—C9—C8	−178.9 (2)	C20—C21—C16—C15	−178.0 (2)
O24—C20—C19—O22	0.2 (3)	C11—C10—C9—C8	0.0 (4)
O24—C20—C19—C18	179.5 (2)	C11—N2—C3—C4	−0.7 (4)
C25—O24—C20—C21	10.9 (4)	C11—C6—C7—C8	1.4 (4)
C25—O24—C20—C19	−169.4 (2)	C7—C6—C11—C10	−1.3 (4)
N2—C3—C4—C5	−0.6 (4)	C7—C6—C11—N2	176.7 (2)
C5—C6—C11—C10	−178.6 (2)	C7—C8—C9—C10	0.2 (4)
C5—C6—C11—N2	−0.7 (4)	C3—N2—C11—C10	179.3 (2)
C5—C6—C7—C8	178.5 (3)	C3—N2—C11—C6	1.3 (4)
C17—C18—C19—O22	178.7 (2)	C9—C10—C11—N2	−177.5 (2)
C17—C18—C19—C20	−0.5 (4)	C9—C10—C11—C6	0.6 (4)
C14—C15—C16—C17	23.3 (3)	C9—C8—C7—C6	−0.9 (4)
C14—C15—C16—C21	−159.1 (3)	C4—C5—C6—C11	−0.6 (4)
C21—C20—C19—O22	180.0 (2)	C4—C5—C6—C7	−177.7 (3)
C21—C20—C19—C18	−0.7 (4)

Hydrogen-bond geometry (Å, º) top

Cg5 and Cg6 are the centroids of the N2–C11 and C6–C11 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O22ⁱ	0.95	2.39	3.330 (3)	169
C15—H15B···O12ⁱⁱ	0.99	2.51	3.425 (3)	153
C8—H8···Cg5ⁱⁱⁱ	0.95	2.82	3.389 (3)	119
C8—H8···Cg6ⁱⁱⁱ	0.95	2.89	3.745 (3)	150

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

Hydrogen-bond geometry (Å, º) top

Cg5 and Cg6 are the centroids of the N2–C11 and C6–C11 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O22ⁱ	0.95	2.39	3.330 (3)	169
C15—H15B···O12ⁱⁱ	0.99	2.51	3.425 (3)	153
C8—H8···Cg5ⁱⁱⁱ	0.95	2.82	3.389 (3)	119
C8—H8···Cg6ⁱⁱⁱ	0.95	2.89	3.745 (3)	150

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

Experimental details

Crystal data
Chemical formula	[Pt(C₉H₆NO)(C₁₁H₁₃O₂)]
M_r	516.45
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	13.2250 (5), 15.0844 (6), 8.4294 (3)
β (°)	93.951 (3)
V (Å³)	1677.59 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	8.38
Crystal size (mm)	0.2 × 0.1 × 0.1

Data collection
Diffractometer	Agilent SuperNova (single source at offset, Eos detector)
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2012)
T_min, T_max	0.715, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	17650, 3429, 3106
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.015, 0.034, 1.05
No. of reflections	3429
No. of parameters	228
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.44

Computer programs: CrysAlis PRO (Agilent, 2012), SHELXS97 (Sheldrick, 2008), SHELXL2014 (Sheldrick, 2015), OLEX2 (Dolomanov et al., 2009).

Acknowledgements

The authors thank VLIR–UOS for financial support through project ZEIN2014Z182 and the Hercules Foundation for supporting the purchase of the diffractometer through project AKUL/09/0035.

References

Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Da, T. T., Chi, N. T. T., Van Meervelt, L., Mangwala Kimpende, P. M. & Dinh, N. H. (2015a). Polyhedron, 85, 104–109. CSD CrossRef Google Scholar
Da, T. T., Hai, L. T. H., Van Meervelt, L. & Dinh, N. H. (2015b). J. Coord. Chem. 68, 3525–3536. CrossRef Google Scholar
Da, T. T., Kim, Y.-M., Chi, N. T. T., Chien, L. X., Minh, N. V. & Dinh, N. H. (2008). Organometallics, 27, 3611–3613. Web of Science CSD CrossRef CAS Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Mangwala Kimpende, P., Thi Da, T., Nguyen Huu, D. & Van Meervelt, L. (2014). Acta Cryst. E70, 435–437. CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar

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Volume 1| Part 1| January 2016| x152428

doi:10.1107/S2414314615024281

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