Dichloridobis[3-(4-meth­oxy­phen­yl)-2-methyl-5-(piperidin-1-yl)-2,3-di­hydro-1,2,4-oxa­diazole-κN4]platinum(II)

Kritchenkov, A.S.; Lavnevich, L.V.; Starova, G.L.; Bokach, N.A.; Kalibabchuk, V.A.

doi:10.1107/S1600536813018059

metal-organic compounds

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ISSN: 2056-9890

Volume 69| Part 8| August 2013| Pages m435-m436

doi:10.1107/S1600536813018059

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Dichloridobis[3-(4-methoxyphenyl)-2-methyl-5-(piperidin-1-yl)-2,3-dihydro-1,2,4-oxadiazole-κN⁴]platinum(II)

Andreii S. Kritchenkov,^a Leonid V. Lavnevich,^a Galina L. Starova,^a Nadezhda A. Bokach ^a and Valentina A. Kalibabchuk ^b ^*

^aDepartment of Chemistry, Saint Petersburg State University, Universitetsky Pr. 26, 198504 Stary Petergof, Russian Federation, and ^bO.O. Bohomolets National Medical University, Department of General Chemistry, Shevchenko blvd. 13, 01004 Kiev, Ukraine
^*Correspondence e-mail: kalibabchuk@ukr.net

(Received 22 June 2013; accepted 1 July 2013; online 6 July 2013)

In title compound, [PtCl₂(C₁₅H₂₁N₃O₂)₂], the Pt^II cation, located on an inversion center, is coordinated by two Cl⁻ anions and two 3-(4-methoxyphenyl)-2-methyl-5-(piperidin-1-yl)-2,3-dihydro-1,2,4-oxadiazole ligands in a distorted Cl₂N₂ square-planar geometry. The dihydrooxadiazole and piperidine rings display envelope (with the non-coordinating N atom as the flap atom) and chair conformations, respectively. In the crystal, weak C—H⋯Cl hydrogen bonds link the molecules into supramolecular chains running along the b axis. The piperidine ring is disordered over two positions with the occupancy ratio of 0.528 (4):0.472 (4).

Related literature

For applications of platinum species bearing N-bound 2,3-dihydro-1,2,4-oxadiazoles, see: Coley et al. (2008 ); Wagner et al. (2010 ). For the synthesis of platinum complexes bearing 2,3-dihydro-1,2,4-oxadiazole ligands, see: Kritchenkov et al. (2011 ). For related structures, see: Bokach & Kukushkin (2006 ); Bokach et al. (2011 ); Fritsky et al. (2006 ); Penkova et al. (2009 ). For standard bond lengths, see: Allen et al. (1987 ).

Experimental

Crystal data

[PtCl₂(C₁₅H₂₁N₃O₂)₂]
M_r = 816.69
Monoclinic, P 2₁ /n
a = 12.77795 (19) Å
b = 8.57581 (15) Å
c = 15.1086 (3) Å
β = 95.0717 (17)°
V = 1649.13 (5) Å³
Z = 2
Mo Kα radiation
μ = 4.46 mm⁻¹
T = 100 K
0.22 × 0.18 × 0.15 mm

Data collection

Agilent Xcalibur Eos diffractometer
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997 ) T_min = 0.617, T_max = 1.000
13705 measured reflections
5072 independent reflections
3997 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.020
wR(F²) = 0.042
S = 1.05
5072 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 1.00 e Å⁻³
Δρ_min = −0.64 e Å⁻³

Table 1
Selected bond lengths (Å)

Pt1—N3	2.0293 (16)
Pt1—Cl1	2.3108 (5)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14C⋯Cl1ⁱ	0.96	2.76	3.423 (3)	127
Symmetry code: (i) $[-x-{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2012 ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: DIAMOND (Brandenburg, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813018059/xu5715sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813018059/xu5715Isup2.hkl

checkCIF report

Comment top

In the past decade, a great attention has been paid to metal-mediated cycloaddition (CA) of dipoles to nitriles because the activation of nitrile substrates by a suitable metal center often results in promotion of CAs, which are not feasible in so-called pure organic chemistry (Coley et al., 2008, Wagner et al., 2010). Thus, the metal-mediated CA represents an efficient route to free and/or coordinated heterocycles that could be either difficult to obtain or even inaccessible via metal-free protocols (Bokach et al., 2006, 2011). Furthermore, an interest in 2,3-dihydro-1,2,4-oxadiazole and their platinum complexes is caused by their potential application in medicine. Despite 2,3-dihydro-1,2,4-oxadiazoles are known, examples of 5-dialkylamino-2,3-dihydro-1,2,4-oxadiazoles and, in particular, their metal complexes are rare. Therefore, the synthesis of new complexes bearing the rare heterocycles as ligands and investigation of their properties, including their biological activity, are of interest. As an amplification of our project focused on metal-mediated CA and reactivity of metal-bound dialkylcyanamides (Kritchenkov et al., 2011)) we synthesized and characterized the title compound by a single-crystal X-ray diffraction.

In the crystal structure of the title compound, the Pt atom is in the inversion center and coordinated by two Cl atoms and two N atoms (Fig. 1) of the heterocycles in trans-position. The Pt(1)–N(3) bond length (Table 1) is typical for (imine)Pt^II species (Allen et al., 1987). The N(3)–C(2) (1.307 (3) Å) distance is characteristic for the N=C double bond (Fritsky et al., 2006; Penkova et al., 2009), while the N(3)–C(4) and N(5)–C(4) (1.472 (3) and 1.480 (3) Å), correspondingly, are specific for the N–C single bonds (Allen et al., 1987). In the complex, the C(4) atom of the heterocyclic ligand exhibits the RR/SS configuration.

In the crystal structure, the complexes interact with each other via the weak C—H···Cl hydrogen bond (Table 2), forming the supramolecular chains running along the b axis.

Related literature top

For applications of platinum species bearing N-bound 2,3-dihydro-1,2,4-oxadiazoles, see: Coley et al. (2008); Wagner et al. (2010). For the synthesis of platinum complexes bearing 2,3-dihydro-1,2,4-oxadiazole ligands, see: Kritchenkov et al. (2011). For related structures, see: Bokach & Kukushkin (2006); Bokach et al. (2011); Fritsky et al. (2006); Penkova et al. (2009). For standard bond lengths, see: Allen et al. (1987).

Experimental top

Title compound was synthesized and isolated as pure solid by the described method (Kritchenkov et al., 2011). The crystal was obtained by a slow evaporation of chloroform (RT) solution of the title compound. Hexane was added to the solution for improvement of crystallization of the complex.

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: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. View to the C₃₀H₄₂Cl₂N₆O₄Pt complex in the structure of 1. Thermal ellipsoids are drawn at the 50% probability level.

Dichloridobis[3-(4-methoxyphenyl)-2-methyl-5-(piperidin-1-yl)-2,3-dihydro-1,2,4-oxadiazole-κN⁴]platinum(II) top

Crystal data top

[PtCl₂(C₁₅H₂₁N₃O₂)₂]	F(000) = 816
M_r = 816.69	D_x = 1.645 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6284 reflections
a = 12.77795 (19) Å	θ = 2.7–31.7°
b = 8.57581 (15) Å	µ = 4.46 mm⁻¹
c = 15.1086 (3) Å	T = 100 K
β = 95.0717 (17)°	Prizm, light-yellow
V = 1649.13 (5) Å³	0.22 × 0.18 × 0.15 mm
Z = 2

Data collection top

Agilent Xcalibur Eos diffractometer	5072 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3997 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
Detector resolution: 16.2096 pixels mm^-1	θ_max = 31.8°, θ_min = 2.7°
ω scans	h = −18→17
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)	k = −11→11
T_min = 0.617, T_max = 1.000	l = −21→21
13705 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.020	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.042	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0128P)²] where P = (F_o² + 2F_c²)/3
5072 reflections	(Δ/σ)_max = 0.001
253 parameters	Δρ_max = 1.00 e Å⁻³
0 restraints	Δρ_min = −0.64 e Å⁻³

Crystal data top

[PtCl₂(C₁₅H₂₁N₃O₂)₂]	V = 1649.13 (5) Å³
M_r = 816.69	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.77795 (19) Å	µ = 4.46 mm⁻¹
b = 8.57581 (15) Å	T = 100 K
c = 15.1086 (3) Å	0.22 × 0.18 × 0.15 mm
β = 95.0717 (17)°

Data collection top

Agilent Xcalibur Eos diffractometer	5072 independent reflections
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)	3997 reflections with I > 2σ(I)
T_min = 0.617, T_max = 1.000	R_int = 0.026
13705 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.020	0 restraints
wR(F²) = 0.042	H-atom parameters constrained
S = 1.05	Δρ_max = 1.00 e Å⁻³
5072 reflections	Δρ_min = −0.64 e Å⁻³
253 parameters

Special details top

Experimental. The piperidine ring was found to be disordered over two positions with the occupancies 0.528/0.472. The non-hydrogen atoms were refined anisotropically. Carbon- and nitrogen-bonded H atoms were placed in calculated positions and were included in the refinement in the "riding" model approximation, with U_iso(H) set to 1.5U_eq(C) and C—H 0.96 Å for the methyl groups, 1.2U_eq(C) and C—H 0.98 Å for the tertiary CH groups, 1.2U_eq(C) and C—H 0.93 Å for the carbon atoms of the benzene rings, and 1.2Ueq(N) and N—H 0.91 Å for the tertiary NH groups.

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Pt1	0.0000	0.5000	0.0000	0.01251 (3)
Cl1	−0.01009 (4)	0.73071 (6)	0.07781 (3)	0.02001 (11)
N3	0.13951 (13)	0.4505 (2)	0.06907 (11)	0.0160 (4)
N5	0.24273 (14)	0.3416 (2)	0.18442 (12)	0.0217 (4)
O1	0.30566 (12)	0.4436 (2)	0.12999 (11)	0.0321 (4)
O13	−0.17565 (13)	0.0800 (2)	0.31245 (12)	0.0383 (4)
C2	0.23174 (17)	0.5175 (3)	0.07460 (16)	0.0246 (5)
C4	0.15295 (15)	0.3037 (2)	0.11921 (13)	0.0177 (4)
H4	0.1726	0.2199	0.0798	0.021*
C6	0.31081 (18)	0.2079 (3)	0.20773 (16)	0.0315 (6)
H6A	0.2708	0.1275	0.2334	0.047*
H6B	0.3674	0.2397	0.2499	0.047*
H6C	0.3389	0.1687	0.1552	0.047*
C7	0.06220 (15)	0.2522 (2)	0.16910 (13)	0.0164 (4)
C8	0.04130 (17)	0.0942 (3)	0.17501 (14)	0.0215 (5)
H8	0.0805	0.0232	0.1451	0.026*
C9	−0.03721 (18)	0.0406 (3)	0.22485 (16)	0.0251 (5)
H9	−0.0492	−0.0659	0.2295	0.030*
C10	−0.09774 (17)	0.1454 (3)	0.26766 (14)	0.0239 (5)
C11	−0.07848 (17)	0.3051 (3)	0.26166 (13)	0.0229 (5)
H11	−0.1193	0.3761	0.2899	0.027*
C12	0.00224 (17)	0.3571 (3)	0.21309 (13)	0.0201 (5)
H12	0.0162	0.4633	0.2100	0.024*
C14	−0.2437 (2)	0.1821 (4)	0.3538 (2)	0.0573 (9)
H14A	−0.2750	0.2542	0.3106	0.086*
H14B	−0.2043	0.2386	0.4004	0.086*
H14C	−0.2978	0.1226	0.3783	0.086*
N1A	0.2753 (9)	0.6289 (16)	0.0262 (9)	0.024 (2)	0.528 (4)
C16A	0.2130 (12)	0.7065 (14)	−0.0497 (9)	0.0144 (16)	0.528 (4)
H16A	0.1405	0.6719	−0.0531	0.017*	0.528 (4)
H16B	0.2417	0.6808	−0.1052	0.017*	0.528 (4)
C17A	0.2194 (3)	0.8876 (5)	−0.0328 (3)	0.0284 (12)	0.528 (4)
H17A	0.1838	0.9418	−0.0832	0.034*	0.528 (4)
H17B	0.1837	0.9130	0.0194	0.034*	0.528 (4)
C18A	0.3334 (4)	0.9427 (6)	−0.0193 (3)	0.0326 (13)	0.528 (4)
H18A	0.3667	0.9297	−0.0740	0.039*	0.528 (4)
H18B	0.3353	1.0526	−0.0040	0.039*	0.528 (4)
C19A	0.3931 (5)	0.8491 (7)	0.0547 (4)	0.0465 (18)	0.528 (4)
H19A	0.4664	0.8797	0.0595	0.056*	0.528 (4)
H19B	0.3650	0.8729	0.1107	0.056*	0.528 (4)
C20A	0.3849 (4)	0.6741 (7)	0.0376 (4)	0.0412 (16)	0.528 (4)
H20A	0.4188	0.6479	−0.0154	0.049*	0.528 (4)
H20B	0.4202	0.6178	0.0873	0.049*	0.528 (4)
N1B	0.2575 (10)	0.6571 (17)	0.0444 (10)	0.0193 (18)	0.472 (4)
C16B	0.2104 (14)	0.7419 (16)	−0.0325 (10)	0.022 (2)	0.472 (4)
H16C	0.1836	0.8409	−0.0133	0.026*	0.472 (4)
H16D	0.1518	0.6825	−0.0602	0.026*	0.472 (4)
C17B	0.2883 (4)	0.7704 (7)	−0.0991 (3)	0.0319 (14)	0.472 (4)
H17C	0.2550	0.8296	−0.1485	0.038*	0.472 (4)
H17D	0.3109	0.6714	−0.1219	0.038*	0.472 (4)
C18B	0.3841 (4)	0.8600 (7)	−0.0579 (4)	0.0354 (15)	0.472 (4)
H18C	0.3632	0.9635	−0.0406	0.043*	0.472 (4)
H18D	0.4355	0.8707	−0.1010	0.043*	0.472 (4)
C19B	0.4330 (5)	0.7707 (9)	0.0244 (4)	0.0401 (17)	0.472 (4)
H19C	0.4602	0.6712	0.0062	0.048*	0.472 (4)
H19D	0.4910	0.8302	0.0531	0.048*	0.472 (4)
C20B	0.3518 (4)	0.7444 (7)	0.0884 (4)	0.0313 (15)	0.472 (4)
H20C	0.3290	0.8440	0.1102	0.038*	0.472 (4)
H20D	0.3823	0.6848	0.1388	0.038*	0.472 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pt1	0.00901 (5)	0.01308 (6)	0.01504 (5)	−0.00236 (4)	−0.00124 (3)	−0.00214 (5)
Cl1	0.0188 (2)	0.0172 (3)	0.0235 (2)	−0.00130 (19)	−0.00079 (19)	−0.0069 (2)
N3	0.0136 (8)	0.0151 (8)	0.0185 (9)	−0.0028 (6)	−0.0025 (7)	0.0011 (7)
N5	0.0157 (9)	0.0199 (10)	0.0283 (10)	−0.0044 (7)	−0.0048 (8)	0.0064 (8)
O1	0.0148 (8)	0.0358 (9)	0.0435 (10)	−0.0079 (7)	−0.0099 (7)	0.0215 (8)
O13	0.0265 (10)	0.0429 (11)	0.0482 (11)	−0.0006 (8)	0.0184 (8)	0.0072 (9)
C2	0.0170 (10)	0.0261 (13)	0.0292 (12)	−0.0034 (9)	−0.0059 (9)	0.0084 (10)
C4	0.0147 (10)	0.0155 (11)	0.0223 (11)	0.0003 (8)	−0.0016 (8)	−0.0010 (8)
C6	0.0219 (12)	0.0269 (13)	0.0441 (15)	0.0002 (10)	−0.0059 (11)	0.0114 (11)
C7	0.0116 (9)	0.0200 (11)	0.0166 (10)	−0.0031 (8)	−0.0033 (7)	0.0008 (8)
C8	0.0200 (11)	0.0199 (12)	0.0249 (11)	−0.0012 (9)	0.0038 (9)	−0.0053 (9)
C9	0.0225 (12)	0.0213 (12)	0.0318 (13)	−0.0069 (9)	0.0037 (10)	−0.0019 (9)
C10	0.0182 (11)	0.0328 (14)	0.0207 (11)	−0.0034 (9)	0.0028 (9)	0.0021 (10)
C11	0.0215 (11)	0.0296 (13)	0.0176 (10)	0.0065 (9)	0.0023 (9)	−0.0039 (9)
C12	0.0229 (11)	0.0172 (11)	0.0189 (11)	−0.0002 (8)	−0.0047 (9)	−0.0023 (9)
C14	0.0452 (19)	0.067 (2)	0.065 (2)	0.0210 (16)	0.0385 (16)	0.0228 (17)
N1A	0.005 (3)	0.029 (5)	0.038 (6)	0.001 (2)	−0.001 (3)	0.013 (4)
C16A	0.015 (2)	0.011 (4)	0.016 (4)	−0.006 (3)	−0.007 (3)	−0.002 (3)
C17A	0.025 (2)	0.027 (3)	0.033 (3)	−0.0048 (18)	0.0040 (19)	0.004 (2)
C18A	0.033 (3)	0.029 (3)	0.033 (3)	−0.018 (2)	−0.008 (2)	0.009 (2)
C19A	0.039 (4)	0.048 (4)	0.047 (4)	−0.029 (3)	−0.025 (3)	0.023 (3)
C20A	0.018 (2)	0.047 (4)	0.056 (4)	−0.010 (2)	−0.010 (2)	0.031 (3)
N1B	0.006 (4)	0.023 (5)	0.029 (5)	−0.007 (3)	−0.002 (3)	0.006 (3)
C16B	0.019 (3)	0.021 (7)	0.026 (6)	−0.010 (4)	−0.005 (4)	−0.002 (4)
C17B	0.025 (3)	0.045 (3)	0.025 (3)	−0.014 (2)	−0.004 (2)	0.010 (2)
C18B	0.023 (3)	0.042 (4)	0.041 (3)	−0.019 (2)	−0.002 (2)	0.009 (3)
C19B	0.026 (3)	0.054 (5)	0.038 (4)	−0.020 (3)	−0.011 (3)	0.016 (3)
C20B	0.033 (3)	0.030 (3)	0.028 (3)	−0.022 (2)	−0.014 (2)	0.008 (2)

Geometric parameters (Å, º) top

Pt1—N3ⁱ	2.0293 (16)	N1A—C20A	1.449 (14)
Pt1—N3	2.0293 (16)	N1A—C16A	1.49 (2)
Pt1—Cl1ⁱ	2.3108 (5)	C16A—C17A	1.574 (11)
Pt1—Cl1	2.3108 (5)	C16A—H16A	0.9700
N3—C2	1.307 (3)	C16A—H16B	0.9700
N3—C4	1.471 (3)	C17A—C18A	1.528 (6)
N5—C6	1.463 (3)	C17A—H17A	0.9700
N5—C4	1.481 (2)	C17A—H17B	0.9700
N5—O1	1.485 (2)	C18A—C19A	1.525 (7)
O1—C2	1.362 (2)	C18A—H18A	0.9700
O13—C10	1.372 (3)	C18A—H18B	0.9700
O13—C14	1.417 (3)	C19A—C20A	1.525 (9)
C2—N1B	1.333 (17)	C19A—H19A	0.9700
C2—N1A	1.353 (16)	C19A—H19B	0.9700
C4—C7	1.504 (3)	C20A—H20A	0.9700
C4—H4	0.9800	C20A—H20B	0.9700
C6—H6A	0.9600	N1B—C16B	1.45 (2)
C6—H6B	0.9600	N1B—C20B	1.520 (16)
C6—H6C	0.9600	C16B—C17B	1.496 (18)
C7—C8	1.386 (3)	C16B—H16C	0.9700
C7—C12	1.389 (3)	C16B—H16D	0.9700
C8—C9	1.385 (3)	C17B—C18B	1.530 (6)
C8—H8	0.9300	C17B—H17C	0.9700
C9—C10	1.383 (3)	C17B—H17D	0.9700
C9—H9	0.9300	C18B—C19B	1.544 (8)
C10—C11	1.395 (3)	C18B—H18C	0.9700
C11—C12	1.391 (3)	C18B—H18D	0.9700
C11—H11	0.9300	C19B—C20B	1.497 (10)
C12—H12	0.9300	C19B—H19C	0.9700
C14—H14A	0.9600	C19B—H19D	0.9700
C14—H14B	0.9600	C20B—H20C	0.9700
C14—H14C	0.9600	C20B—H20D	0.9700

N3ⁱ—Pt1—N3	180.0	C17A—C16A—H16A	110.2
N3ⁱ—Pt1—Cl1ⁱ	90.20 (5)	N1A—C16A—H16B	110.2
N3—Pt1—Cl1ⁱ	89.80 (5)	C17A—C16A—H16B	110.2
N3ⁱ—Pt1—Cl1	89.80 (5)	H16A—C16A—H16B	108.5
N3—Pt1—Cl1	90.20 (5)	C18A—C17A—C16A	111.2 (7)
Cl1ⁱ—Pt1—Cl1	180.0	C18A—C17A—H17A	109.4
C2—N3—C4	106.24 (16)	C16A—C17A—H17A	109.4
C2—N3—Pt1	133.39 (15)	C18A—C17A—H17B	109.4
C4—N3—Pt1	120.06 (12)	C16A—C17A—H17B	109.4
C6—N5—C4	113.41 (17)	H17A—C17A—H17B	108.0
C6—N5—O1	104.81 (17)	C19A—C18A—C17A	110.2 (4)
C4—N5—O1	100.75 (14)	C19A—C18A—H18A	109.6
C2—O1—N5	103.55 (16)	C17A—C18A—H18A	109.6
C10—O13—C14	117.7 (2)	C19A—C18A—H18B	109.6
N3—C2—N1B	128.4 (6)	C17A—C18A—H18B	109.6
N3—C2—N1A	133.4 (6)	H18A—C18A—H18B	108.1
N1B—C2—N1A	19.0 (6)	C20A—C19A—C18A	111.8 (4)
N3—C2—O1	114.03 (19)	C20A—C19A—H19A	109.3
N1B—C2—O1	116.7 (6)	C18A—C19A—H19A	109.3
N1A—C2—O1	111.4 (6)	C20A—C19A—H19B	109.3
N3—C4—N5	101.72 (15)	C18A—C19A—H19B	109.3
N3—C4—C7	116.68 (17)	H19A—C19A—H19B	107.9
N5—C4—C7	108.50 (16)	N1A—C20A—C19A	109.5 (7)
N3—C4—H4	109.8	N1A—C20A—H20A	109.8
N5—C4—H4	109.8	C19A—C20A—H20A	109.8
C7—C4—H4	109.8	N1A—C20A—H20B	109.8
N5—C6—H6A	109.5	C19A—C20A—H20B	109.8
N5—C6—H6B	109.5	H20A—C20A—H20B	108.2
H6A—C6—H6B	109.5	C2—N1B—C16B	128.7 (13)
N5—C6—H6C	109.5	C2—N1B—C20B	120.2 (12)
H6A—C6—H6C	109.5	C16B—N1B—C20B	111.1 (12)
H6B—C6—H6C	109.5	N1B—C16B—C17B	111.5 (12)
C8—C7—C12	119.0 (2)	N1B—C16B—H16C	109.3
C8—C7—C4	118.74 (19)	C17B—C16B—H16C	109.3
C12—C7—C4	122.15 (19)	N1B—C16B—H16D	109.3
C9—C8—C7	120.8 (2)	C17B—C16B—H16D	109.3
C9—C8—H8	119.6	H16C—C16B—H16D	108.0
C7—C8—H8	119.6	C16B—C17B—C18B	111.4 (6)
C10—C9—C8	120.0 (2)	C16B—C17B—H17C	109.4
C10—C9—H9	120.0	C18B—C17B—H17C	109.4
C8—C9—H9	120.0	C16B—C17B—H17D	109.4
O13—C10—C9	115.2 (2)	C18B—C17B—H17D	109.4
O13—C10—C11	125.0 (2)	H17C—C17B—H17D	108.0
C9—C10—C11	119.9 (2)	C17B—C18B—C19B	109.3 (4)
C12—C11—C10	119.5 (2)	C17B—C18B—H18C	109.8
C12—C11—H11	120.2	C19B—C18B—H18C	109.8
C10—C11—H11	120.2	C17B—C18B—H18D	109.8
C7—C12—C11	120.7 (2)	C19B—C18B—H18D	109.8
C7—C12—H12	119.6	H18C—C18B—H18D	108.3
C11—C12—H12	119.6	C20B—C19B—C18B	109.9 (5)
O13—C14—H14A	109.5	C20B—C19B—H19C	109.7
O13—C14—H14B	109.5	C18B—C19B—H19C	109.7
H14A—C14—H14B	109.5	C20B—C19B—H19D	109.7
O13—C14—H14C	109.5	C18B—C19B—H19D	109.7
H14A—C14—H14C	109.5	H19C—C19B—H19D	108.2
H14B—C14—H14C	109.5	C19B—C20B—N1B	111.0 (7)
C2—N1A—C20A	124.3 (11)	C19B—C20B—H20C	109.4
C2—N1A—C16A	120.9 (11)	N1B—C20B—H20C	109.4
C20A—N1A—C16A	114.6 (12)	C19B—C20B—H20D	109.4
N1A—C16A—C17A	107.4 (8)	N1B—C20B—H20D	109.4
N1A—C16A—H16A	110.2	H20C—C20B—H20D	108.0

N3ⁱ—Pt1—N3—C2	−49 (15)	C8—C9—C10—C11	−1.0 (3)
Cl1ⁱ—Pt1—N3—C2	116.2 (2)	O13—C10—C11—C12	−179.11 (19)
Cl1—Pt1—N3—C2	−63.8 (2)	C9—C10—C11—C12	−0.5 (3)
N3ⁱ—Pt1—N3—C4	138 (15)	C8—C7—C12—C11	−0.7 (3)
Cl1ⁱ—Pt1—N3—C4	−56.47 (15)	C4—C7—C12—C11	−177.36 (17)
Cl1—Pt1—N3—C4	123.53 (15)	C10—C11—C12—C7	1.4 (3)
C6—N5—O1—C2	150.49 (18)	N3—C2—N1A—C20A	−172.2 (6)
C4—N5—O1—C2	32.6 (2)	N1B—C2—N1A—C20A	105 (4)
C4—N3—C2—N1B	−175.5 (7)	O1—C2—N1A—C20A	−5.4 (10)
Pt1—N3—C2—N1B	11.1 (8)	N3—C2—N1A—C16A	2.7 (12)
C4—N3—C2—N1A	160.1 (6)	N1B—C2—N1A—C16A	−80 (4)
Pt1—N3—C2—N1A	−13.3 (7)	O1—C2—N1A—C16A	169.5 (7)
C4—N3—C2—O1	−6.4 (3)	C2—N1A—C16A—C17A	125.3 (10)
Pt1—N3—C2—O1	−179.78 (15)	C20A—N1A—C16A—C17A	−59.3 (12)
N5—O1—C2—N3	−17.2 (3)	N1A—C16A—C17A—C18A	55.0 (11)
N5—O1—C2—N1B	153.3 (5)	C16A—C17A—C18A—C19A	−54.4 (8)
N5—O1—C2—N1A	173.3 (5)	C17A—C18A—C19A—C20A	54.6 (8)
C2—N3—C4—N5	27.1 (2)	C2—N1A—C20A—C19A	−124.4 (8)
Pt1—N3—C4—N5	−158.46 (13)	C16A—N1A—C20A—C19A	60.3 (10)
C2—N3—C4—C7	144.93 (19)	C18A—C19A—C20A—N1A	−56.2 (9)
Pt1—N3—C4—C7	−40.6 (2)	N3—C2—N1B—C16B	−30.5 (13)
C6—N5—C4—N3	−146.99 (18)	N1A—C2—N1B—C16B	83 (4)
O1—N5—C4—N3	−35.54 (19)	O1—C2—N1B—C16B	160.6 (9)
C6—N5—C4—C7	89.4 (2)	N3—C2—N1B—C20B	153.6 (5)
O1—N5—C4—C7	−159.12 (16)	N1A—C2—N1B—C20B	−93 (4)
N3—C4—C7—C8	144.73 (18)	O1—C2—N1B—C20B	−15.2 (9)
N5—C4—C7—C8	−101.2 (2)	C2—N1B—C16B—C17B	−118.6 (11)
N3—C4—C7—C12	−38.6 (3)	C20B—N1B—C16B—C17B	57.6 (10)
N5—C4—C7—C12	75.5 (2)	N1B—C16B—C17B—C18B	−57.4 (11)
C12—C7—C8—C9	−0.8 (3)	C16B—C17B—C18B—C19B	55.5 (9)
C4—C7—C8—C9	175.95 (18)	C17B—C18B—C19B—C20B	−55.6 (7)
C7—C8—C9—C10	1.7 (3)	C18B—C19B—C20B—N1B	56.9 (9)
C14—O13—C10—C9	−176.8 (2)	C2—N1B—C20B—C19B	118.3 (8)
C14—O13—C10—C11	1.8 (3)	C16B—N1B—C20B—C19B	−58.2 (10)
C8—C9—C10—O13	177.74 (19)

Symmetry code: (i) −x, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14C···Cl1ⁱⁱ	0.96	2.76	3.423 (3)	127

Symmetry code: (ii) −x−1/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[PtCl₂(C₁₅H₂₁N₃O₂)₂]
M_r	816.69
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	12.77795 (19), 8.57581 (15), 15.1086 (3)
β (°)	95.0717 (17)
V (Å³)	1649.13 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	4.46
Crystal size (mm)	0.22 × 0.18 × 0.15

Data collection
Diffractometer	Agilent Xcalibur Eos diffractometer
Absorption correction	Multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)
T_min, T_max	0.617, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	13705, 5072, 3997
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.742

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.020, 0.042, 1.05
No. of reflections	5072
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.00, −0.64

Computer programs: CrysAlis PRO (Agilent, 2012), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2009).

Selected bond lengths (Å) top

Pt1—N3

2.0293 (16)

Pt1—Cl1

2.3108 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14C···Cl1ⁱ	0.96	2.76	3.423 (3)	127

Symmetry code: (i) −x−1/2, y−1/2, −z+1/2.

Acknowledgements

This work was supported by a Saint Petersburg State University research grant (2013–2015, 12.38.781.2013) and the RFBR 12–03–33071. The XRD study was performed at the X-ray Diffraction Centre of Saint Petersburg State University.

References

Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bokach, N. A., Balova, I. A., Haukka, M. & Kukushkin, V. Y. (2011). Organometallics, 30, 595–602. Web of Science CSD CrossRef CAS Google Scholar
Bokach, N. A. & Kukushkin, V. Y. (2006). Russ. Chem. Bull. 55, 1869–1882. Web of Science CrossRef CAS Google Scholar
Brandenburg, K. (2009). Diamond. Crystal Impact GbR, Bonn, Germany. Google Scholar
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Coley, H. M., Sarju, J. & Wagner, G. (2008). J. Med. Chem. 51, 135–141. Web of Science CrossRef PubMed CAS Google Scholar
Fritsky, I. O., Kozłowski, H., Kanderal, O. M., Haukka, M., Świątek-Kozłowska, J., Gumienna-Kontecka, E. & Meyer, F. (2006). Chem. Commun. pp. 4125–4127. Web of Science CSD CrossRef Google Scholar
Kritchenkov, A. S., Bokach, N. A., Haukka, M. & Kukushkin, V. Y. (2011). Dalton Trans. 40, 4175–4182. Web of Science CSD CrossRef CAS PubMed Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Penkova, L. V., Maciąg, A., Rybak-Akimova, E. V., Haukka, M., Pavlenko, V. A., Iskenderov, T. S., Kozłowski, H., Meyer, F. & Fritsky, I. O. (2009). Inorg. Chem. 48, 6960–6971. Web of Science CSD CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wagner, G., Marchant, A. & Sayer, J. (2010). Dalton Trans. 39, 7747–7759. Web of Science CrossRef CAS PubMed Google Scholar

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