Trichlorido[4-meth­oxy-2,6-bis­(2-pyrimidin-2-yl-κN)phenyl-κC1]platinum(IV) acetonitrile monosolvate

Wu, Y.; Xie, D.; Zhang, D.; Li, X.; Jin, W.

doi:10.1107/S1600536812036410

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 9| September 2012| Pages m1210-m1211

doi:10.1107/S1600536812036410

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Trichlorido[4-methoxy-2,6-bis(2-pyrimidin-2-yl-κN)phenyl-κC¹]platinum(IV) acetonitrile monosolvate

Yang Wu,^a Dahai Xie,^a Dengqing Zhang,^a Xianying Li ^b and Wusong Jin ^a ^*

^aCollege of Chemistry, Chemical Engineering and Biotechnology, Donghua University, 2999 North Renmin Road, Songjiang, Shanghai 201620, People's Republic of China, and ^bSchool of Environmental Science and Engineering, Donghua University, 2999 North Renmin Road, Songjiang, Shanghai 201620, People's Republic of China
^*Correspondence e-mail: wsjin@dhu.edu.cn

(Received 8 June 2012; accepted 21 August 2012; online 25 August 2012)

In the title complex, [Pt(C₁₅H₁₁N₄O)Cl₃]·CH₃CN, the Pt^IV ion adopts a distorted octahedral coordination geometry defined by a tridentate cyclometalated NCN ligand and three Cl atoms. In the crystal, individual molecules are aggregated into a three-dimensional network by C—H⋯Cl hydrogen-bonding interactions and π–π stacking interactions between the tridentate ligands, the shortest ring centroid–centroid distance being 3.613 Å.

Related literature

For general background to the chemistry of the tridentate NCN ligand and its complexes, see: Williams (2009 ); Wang et al. (2010 ); Chen et al. (2009 ); Lu et al. (2009 ). For the synthesis of related ligand, see: Avitia et al. (2011 ); Wakioka et al. (2010 ). For Pt^II complexes with tridentate NCN ligands, see: Kozhevnikov et al. (2008 ); Tam et al. (2011 ). For Pt—Cl bond lengths in other Pt^IV complexes, see: Bagchi et al. (2007 ); Bokach et al. (2012 ). For details of the preparation, see: Cardenas & Echavarren (1999 ).

Experimental

Crystal data

[Pt(C₁₅H₁₁N₄O)Cl₃]·C₂H₃N
M_r = 605.77
Triclinic, $[P \overline 1]$
a = 8.5739 (8) Å
b = 10.3371 (10) Å
c = 12.6610 (12) Å
α = 68.955 (2)°
β = 80.033 (2)°
γ = 70.619 (2)°
V = 986.09 (16) Å³
Z = 2
Mo Kα radiation
μ = 7.54 mm⁻¹
T = 293 K
0.21 × 0.16 × 0.13 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.346, T_max = 1.000
5788 measured reflections
3666 independent reflections
3442 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.085
S = 1.04
3666 reflections
246 parameters
H-atom parameters constrained
Δρ_max = 1.63 e Å⁻³
Δρ_min = −1.61 e Å⁻³

Table 1
Selected bond lengths (Å)

Pt1—C5	1.944 (5)
Pt1—N3	2.038 (4)
Pt1—N1	2.046 (4)
Pt1—Cl3	2.3018 (16)
Pt1—Cl2	2.3528 (15)
Pt1—Cl1	2.4160 (15)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯Cl1ⁱ	0.93	2.61	3.330 (6)	135
C4—H4⋯Cl2ⁱⁱ	0.93	2.84	3.680 (6)	151
C12—H12⋯Cl3ⁱⁱⁱ	0.93	2.78	3.509 (6)	136
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) -x+2, -y+1, -z+2; (iii) x-1, y, z.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812036410/hp2041sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812036410/hp2041Isup2.hkl

checkCIF report

Comment top

Square planar Pt^II complexes with tridentate cyclometalating NCN ligands [e.g., m-di(2-pyridinyl)benzene (dpb) derivatives (Wang et al., 2010)] have attracted a great attention due to their potential application in wide ranges such as chemosensors, luminescent materials, as well as photovoltaic cells (Williams 2009; Chen et al., 2009; Lu et al., 2009). Recently, some Pt^II complex with novel tridentate NCN ligands have been reported (Tam et al., 2011; Kozhevnikov et al., 2008). In this point of view, we develop a novel tridentate NCN ligand (Avitia et al., 2011; Wakioka et al., 2010), 1,3-di(2'-pyrimidyl)-5-methoxybenzene. Interestingly, in an attempt to prepare square Pt^II complex by the reaction of K₂PtCl₄ with newly synthesized ligand, the neutral Pt^IV complex, [Pt(C₁₅H₁₁N₄O)Cl₃].CH₃CN, was unexpected obtained as a byproduct along with the Pt^II complex, [Pt(C₁₅H₁₁N₄O)Cl].

The asymmetric unit of the title compound, contains a neutral Pt^IV complex and one acetonitrile molecule (Fig. 1). The central platinum(IV) atom is coordinated by two nitrogen atoms and one carbon atom from tridentate ligand, and three chlorine atoms forming a distorted octahedral geometry. The angles C5—Pt1—Cl3, N3—Pt1—Cl3, N1—Pt1—Cl3, C5—Pt1—Cl2, Cl3—Pt1—Cl1, N3—Pt1—Cl2, N1—Pt1—Cl2 and Cl2—Pt1—Cl1 (88.14 (13)—92.288 (13)°, Table 1) are very close to the ideal 90°, the deviation from 90° of the angles C5—Pt1—N3 (80.3 (2)°) and C5—Pt1—N1 (80.7 (2)°) are owing to the formation of five-membered chelating rings. The bond lengths of Pt–N1, Pt–C5, Pt–N3, and Pt–Cl1 (Table 1) are similar to the literature reported Pt(II)dpbCl complexes (Wang et al., 2010). The bond lengths of Pt–Cl2 and Pt–Cl3 (Table 1) resemble those in other Pt^IV complexes, which have been published (Bagchi et al., 2007; Bokach et al., 2012). The title complex packed as head-to-tail dimers in the crystal, each molecular unit of the dimer related to the other by a center of inversion. They are further connected into three-dimension crystal structure via C—H···Cl hydrogen-bonding interactions and π–π stacking interactions between tridentate ligands, the shortest ring centroid-centroid distance is 3.613 Å (Table 2).

Related literature top

For general background to the chemistry of the tridentate NCN ligand and its complexes, see: Williams (2009); Wang et al. (2010); Chen et al. (2009); Lu et al. (2009). For the synthesis of related ligand, see: Avitia et al. (2011); Wakioka et al. (2010). For Pt^II complexes with tridentate NCN ligands, see: Kozhevnikov et al. (2008); Tam et al. (2011). For Pt—Cl bond lengths in other Pt^IV complexes, see: Bagchi et al. (2007); Bokach et al. (2012). For details of the preparation, see: Cardenas & Echavarren (1999).

Experimental top

A mixture of 1,3-di(2'-pyrimidyl)-5-methoxybenzene 200 mg (0.756 mmol) and K₂PtCl₄ 314 mg (0.756 mmol) in CH₃CN/H₂O (v/v, 1/1, 60 ml) was stirred under reflux for 24 h in an argon atmosphere (Cardenas & Echavarren,, 1999). The resulted red solution was evaporated and the residue was extracted with CH₂Cl₂. The title complex was separated by flash column chromatography (SiO₂, CH₂Cl₂ as eluent) from the mixture. The single-crystal was obtained by slow evaporation of an acetonitrile solution of the title complex.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Perspective view of the title compound with displacement ellipsoids at the 30% probability level.
	Fig. 2. A view of the unit-cell contents of the title complex.

Trichlorido[4-methoxy-2,6-bis(2-pyrimidin-2-yl-κN)phenyl- κC¹]platinum(IV) acetonitrile monosolvate top

Crystal data top

[Pt(C₁₅H₁₁N₄O)Cl₃]·C₂H₃N	Z = 2
M_r = 605.77	F(000) = 576
Triclinic, P1	D_x = 2.040 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5739 (8) Å	Cell parameters from 3770 reflections
b = 10.3371 (10) Å	θ = 4.6–56.4°
c = 12.6610 (12) Å	µ = 7.54 mm⁻¹
α = 68.955 (2)°	T = 293 K
β = 80.033 (2)°	Prismatic, red
γ = 70.619 (2)°	0.21 × 0.16 × 0.13 mm
V = 986.09 (16) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	3666 independent reflections
Radiation source: fine-focus sealed tube	3442 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
phi and ω scans	θ_max = 25.5°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −9→10
T_min = 0.346, T_max = 1.000	k = −12→11
5788 measured reflections	l = −15→9

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.085	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0539P)²] where P = (F_o² + 2F_c²)/3
3666 reflections	(Δ/σ)_max = 0.002
246 parameters	Δρ_max = 1.63 e Å⁻³
0 restraints	Δρ_min = −1.61 e Å⁻³

Crystal data top

[Pt(C₁₅H₁₁N₄O)Cl₃]·C₂H₃N	γ = 70.619 (2)°
M_r = 605.77	V = 986.09 (16) Å³
Triclinic, P1	Z = 2
a = 8.5739 (8) Å	Mo Kα radiation
b = 10.3371 (10) Å	µ = 7.54 mm⁻¹
c = 12.6610 (12) Å	T = 293 K
α = 68.955 (2)°	0.21 × 0.16 × 0.13 mm
β = 80.033 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3666 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	3442 reflections with I > 2σ(I)
T_min = 0.346, T_max = 1.000	R_int = 0.026
5788 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.085	H-atom parameters constrained
S = 1.04	Δρ_max = 1.63 e Å⁻³
3666 reflections	Δρ_min = −1.61 e Å⁻³
246 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. 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 > σ(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
Pt1	0.69455 (2)	0.665972 (19)	0.713419 (15)	0.03224 (10)
Cl1	0.6637 (2)	0.92214 (17)	0.62623 (15)	0.0597 (5)
Cl2	0.52290 (17)	0.70939 (16)	0.87099 (12)	0.0391 (3)
Cl3	0.8607 (2)	0.6190 (2)	0.55999 (15)	0.0585 (4)
N1	0.9051 (5)	0.6081 (5)	0.7956 (4)	0.0329 (9)
N2	1.1004 (5)	0.4043 (5)	0.9078 (4)	0.0388 (10)
N3	0.5022 (5)	0.6499 (5)	0.6493 (4)	0.0371 (10)
N4	0.3832 (6)	0.4766 (6)	0.6415 (4)	0.0440 (11)
N5	0.0658 (16)	0.0090 (12)	0.7024 (13)	0.160 (5)
O1	0.7849 (6)	0.0280 (4)	0.9438 (4)	0.0601 (13)
C1	0.9599 (6)	0.4644 (6)	0.8559 (4)	0.0356 (11)
C2	0.9942 (6)	0.6958 (6)	0.7895 (4)	0.0374 (12)
H2	0.9576	0.7943	0.7494	0.045*
C3	1.1408 (7)	0.6384 (7)	0.8433 (5)	0.0443 (14)
H3	1.2042	0.6970	0.8410	0.053*
C4	1.1898 (7)	0.4928 (7)	0.9001 (5)	0.0453 (14)
H4	1.2896	0.4530	0.9351	0.054*
C5	0.7221 (7)	0.4595 (5)	0.7844 (5)	0.0355 (12)
C6	0.8542 (6)	0.3786 (6)	0.8534 (5)	0.0368 (11)
C7	0.8712 (7)	0.2321 (6)	0.9065 (5)	0.0444 (13)
H7	0.9557	0.1741	0.9551	0.053*
C8	0.7599 (8)	0.1731 (6)	0.8860 (5)	0.0451 (13)
C9	0.6325 (7)	0.2562 (6)	0.8115 (5)	0.0442 (13)
H9	0.5622	0.2138	0.7965	0.053*
C10	0.6146 (7)	0.4025 (6)	0.7612 (5)	0.0381 (12)
C11	0.4924 (6)	0.5123 (6)	0.6806 (5)	0.0360 (11)
C12	0.2798 (7)	0.5850 (7)	0.5684 (5)	0.0483 (14)
H12	0.2031	0.5635	0.5387	0.058*
C13	0.2806 (8)	0.7262 (8)	0.5348 (5)	0.0498 (15)
H13	0.2053	0.7991	0.4846	0.060*
C14	0.3954 (7)	0.7570 (6)	0.5772 (5)	0.0422 (13)
H14	0.3991	0.8519	0.5560	0.051*
C15	0.7049 (9)	−0.0469 (6)	0.9062 (7)	0.0591 (17)
H15A	0.5871	−0.0096	0.9179	0.089*
H15B	0.7401	−0.1485	0.9485	0.089*
H15C	0.7336	−0.0331	0.8270	0.089*
C16	0.2570 (14)	0.1329 (11)	0.7295 (10)	0.100 (3)
H16A	0.2050	0.2357	0.7068	0.150*
H16B	0.3587	0.1123	0.6845	0.150*
H16C	0.2800	0.0975	0.8081	0.150*
C17	0.1486 (13)	0.0629 (10)	0.7132 (9)	0.092 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pt1	0.03207 (14)	0.03471 (14)	0.03470 (14)	−0.01178 (9)	−0.01267 (9)	−0.01011 (9)
Cl1	0.0748 (11)	0.0444 (8)	0.0617 (10)	−0.0267 (8)	−0.0317 (8)	0.0017 (7)
Cl2	0.0331 (6)	0.0485 (8)	0.0416 (7)	−0.0113 (6)	−0.0103 (5)	−0.0183 (6)
Cl3	0.0460 (8)	0.0979 (13)	0.0518 (9)	−0.0305 (9)	0.0021 (7)	−0.0415 (9)
N1	0.033 (2)	0.038 (2)	0.032 (2)	−0.0095 (18)	−0.0098 (17)	−0.0137 (18)
N2	0.033 (2)	0.048 (3)	0.038 (2)	−0.008 (2)	−0.0151 (18)	−0.015 (2)
N3	0.035 (2)	0.040 (2)	0.041 (2)	−0.0109 (19)	−0.0124 (19)	−0.012 (2)
N4	0.037 (2)	0.054 (3)	0.049 (3)	−0.011 (2)	−0.014 (2)	−0.024 (2)
N5	0.174 (11)	0.130 (9)	0.227 (14)	−0.102 (9)	0.068 (10)	−0.101 (9)
O1	0.077 (3)	0.035 (2)	0.078 (3)	−0.019 (2)	−0.037 (3)	−0.012 (2)
C1	0.035 (3)	0.042 (3)	0.036 (3)	−0.008 (2)	−0.010 (2)	−0.020 (2)
C2	0.036 (3)	0.042 (3)	0.040 (3)	−0.016 (2)	−0.005 (2)	−0.014 (2)
C3	0.040 (3)	0.066 (4)	0.044 (3)	−0.026 (3)	−0.006 (2)	−0.027 (3)
C4	0.031 (3)	0.064 (4)	0.045 (3)	−0.009 (3)	−0.010 (2)	−0.025 (3)
C5	0.038 (3)	0.027 (2)	0.043 (3)	−0.008 (2)	−0.012 (2)	−0.011 (2)
C6	0.034 (3)	0.037 (3)	0.043 (3)	−0.006 (2)	−0.015 (2)	−0.015 (2)
C7	0.048 (3)	0.040 (3)	0.048 (3)	−0.008 (3)	−0.024 (3)	−0.014 (2)
C8	0.050 (3)	0.032 (3)	0.056 (4)	−0.009 (2)	−0.011 (3)	−0.017 (2)
C9	0.046 (3)	0.039 (3)	0.057 (4)	−0.017 (2)	−0.018 (3)	−0.016 (3)
C10	0.037 (3)	0.041 (3)	0.042 (3)	−0.012 (2)	−0.013 (2)	−0.014 (2)
C11	0.033 (3)	0.040 (3)	0.040 (3)	−0.012 (2)	−0.010 (2)	−0.014 (2)
C12	0.036 (3)	0.069 (4)	0.052 (4)	−0.021 (3)	−0.010 (3)	−0.026 (3)
C13	0.042 (3)	0.061 (4)	0.048 (3)	−0.011 (3)	−0.021 (3)	−0.014 (3)
C14	0.043 (3)	0.043 (3)	0.042 (3)	−0.013 (2)	−0.019 (2)	−0.008 (2)
C15	0.071 (4)	0.032 (3)	0.083 (5)	−0.014 (3)	−0.025 (4)	−0.022 (3)
C16	0.088 (6)	0.098 (7)	0.120 (8)	−0.039 (5)	−0.007 (6)	−0.033 (6)
C17	0.100 (7)	0.063 (5)	0.118 (8)	−0.041 (5)	0.021 (6)	−0.032 (5)

Geometric parameters (Å, º) top

Pt1—C5	1.944 (5)	C4—H4	0.9300
Pt1—N3	2.038 (4)	C5—C10	1.364 (8)
Pt1—N1	2.046 (4)	C5—C6	1.391 (7)
Pt1—Cl3	2.3018 (16)	C6—C7	1.387 (8)
Pt1—Cl2	2.3528 (15)	C7—C8	1.391 (8)
Pt1—Cl1	2.4160 (15)	C7—H7	0.9300
N1—C2	1.342 (7)	C8—C9	1.405 (8)
N1—C1	1.363 (7)	C9—C10	1.380 (8)
N2—C1	1.324 (6)	C9—H9	0.9300
N2—C4	1.345 (8)	C10—C11	1.475 (7)
N3—C14	1.337 (7)	C12—C13	1.368 (9)
N3—C11	1.360 (7)	C12—H12	0.9300
N4—C11	1.334 (7)	C13—C14	1.368 (8)
N4—C12	1.334 (8)	C13—H13	0.9300
N5—C17	1.088 (14)	C14—H14	0.9300
O1—C8	1.373 (7)	C15—H15A	0.9600
O1—C15	1.422 (8)	C15—H15B	0.9600
C1—C6	1.474 (7)	C15—H15C	0.9600
C2—C3	1.381 (8)	C16—C17	1.431 (14)
C2—H2	0.9300	C16—H16A	0.9600
C3—C4	1.366 (9)	C16—H16B	0.9600
C3—H3	0.9300	C16—H16C	0.9600

C5—Pt1—N3	80.3 (2)	C7—C6—C1	129.5 (5)
C5—Pt1—N1	80.7 (2)	C5—C6—C1	113.2 (5)
N3—Pt1—N1	160.70 (19)	C6—C7—C8	119.1 (5)
C5—Pt1—Cl3	89.32 (18)	C6—C7—H7	120.5
N3—Pt1—Cl3	88.69 (14)	C8—C7—H7	120.5
N1—Pt1—Cl3	88.14 (13)	O1—C8—C7	114.8 (5)
C5—Pt1—Cl2	89.57 (17)	O1—C8—C9	122.9 (5)
N3—Pt1—Cl2	90.54 (14)	C7—C8—C9	122.3 (5)
N1—Pt1—Cl2	92.28 (13)	C10—C9—C8	118.0 (5)
Cl3—Pt1—Cl2	178.74 (5)	C10—C9—H9	121.0
C5—Pt1—Cl1	179.24 (16)	C8—C9—H9	121.0
N3—Pt1—Cl1	100.49 (13)	C5—C10—C9	118.9 (5)
N1—Pt1—Cl1	98.58 (13)	C5—C10—C11	112.4 (5)
Cl3—Pt1—Cl1	90.63 (7)	C9—C10—C11	128.6 (5)
Cl2—Pt1—Cl1	90.48 (6)	N4—C11—N3	123.5 (5)
C2—N1—C1	119.4 (4)	N4—C11—C10	121.6 (5)
C2—N1—Pt1	126.1 (4)	N3—C11—C10	114.8 (5)
C1—N1—Pt1	114.4 (3)	N4—C12—C13	123.4 (5)
C1—N2—C4	116.8 (5)	N4—C12—H12	118.3
C14—N3—C11	119.1 (5)	C13—C12—H12	118.3
C14—N3—Pt1	126.8 (4)	C12—C13—C14	118.1 (6)
C11—N3—Pt1	114.0 (3)	C12—C13—H13	120.9
C11—N4—C12	116.2 (5)	C14—C13—H13	120.9
C8—O1—C15	117.5 (5)	N3—C14—C13	119.6 (6)
N2—C1—N1	123.3 (5)	N3—C14—H14	120.2
N2—C1—C6	122.2 (5)	C13—C14—H14	120.2
N1—C1—C6	114.4 (4)	O1—C15—H15A	109.5
N1—C2—C3	119.4 (5)	O1—C15—H15B	109.5
N1—C2—H2	120.3	H15A—C15—H15B	109.5
C3—C2—H2	120.3	O1—C15—H15C	109.5
C4—C3—C2	118.0 (5)	H15A—C15—H15C	109.5
C4—C3—H3	121.0	H15B—C15—H15C	109.5
C2—C3—H3	121.0	C17—C16—H16A	109.5
N2—C4—C3	123.1 (5)	C17—C16—H16B	109.5
N2—C4—H4	118.5	H16A—C16—H16B	109.5
C3—C4—H4	118.5	C17—C16—H16C	109.5
C10—C5—C6	124.2 (5)	H16A—C16—H16C	109.5
C10—C5—Pt1	118.4 (4)	H16B—C16—H16C	109.5
C6—C5—Pt1	117.3 (4)	N5—C17—C16	179.0 (14)
C7—C6—C5	117.3 (5)

C5—Pt1—N1—C2	176.2 (5)	Cl2—Pt1—C5—C6	−90.5 (4)
N3—Pt1—N1—C2	167.2 (5)	Cl1—Pt1—C5—C6	4 (14)
Cl3—Pt1—N1—C2	86.5 (4)	C10—C5—C6—C7	−3.6 (9)
Cl2—Pt1—N1—C2	−94.6 (4)	Pt1—C5—C6—C7	178.3 (4)
Cl1—Pt1—N1—C2	−3.8 (4)	C10—C5—C6—C1	174.7 (5)
C5—Pt1—N1—C1	0.1 (4)	Pt1—C5—C6—C1	−3.4 (7)
N3—Pt1—N1—C1	−8.9 (7)	N2—C1—C6—C7	4.6 (9)
Cl3—Pt1—N1—C1	−89.6 (4)	N1—C1—C6—C7	−178.6 (6)
Cl2—Pt1—N1—C1	89.2 (4)	N2—C1—C6—C5	−173.4 (5)
Cl1—Pt1—N1—C1	−179.9 (3)	N1—C1—C6—C5	3.4 (7)
C5—Pt1—N3—C14	−178.9 (5)	C5—C6—C7—C8	1.8 (9)
N1—Pt1—N3—C14	−169.9 (5)	C1—C6—C7—C8	−176.2 (6)
Cl3—Pt1—N3—C14	−89.3 (5)	C15—O1—C8—C7	−164.5 (6)
Cl2—Pt1—N3—C14	91.7 (5)	C15—O1—C8—C9	15.3 (10)
Cl1—Pt1—N3—C14	1.1 (5)	C6—C7—C8—O1	−178.9 (6)
C5—Pt1—N3—C11	−2.8 (4)	C6—C7—C8—C9	1.2 (10)
N1—Pt1—N3—C11	6.2 (8)	O1—C8—C9—C10	177.5 (6)
Cl3—Pt1—N3—C11	86.8 (4)	C7—C8—C9—C10	−2.7 (9)
Cl2—Pt1—N3—C11	−92.3 (4)	C6—C5—C10—C9	2.2 (9)
Cl1—Pt1—N3—C11	177.2 (4)	Pt1—C5—C10—C9	−179.8 (4)
C4—N2—C1—N1	0.8 (8)	C6—C5—C10—C11	−176.8 (5)
C4—N2—C1—C6	177.2 (5)	Pt1—C5—C10—C11	1.3 (7)
C2—N1—C1—N2	−1.5 (8)	C8—C9—C10—C5	1.0 (9)
Pt1—N1—C1—N2	174.9 (4)	C8—C9—C10—C11	179.8 (6)
C2—N1—C1—C6	−178.2 (5)	C12—N4—C11—N3	−0.3 (8)
Pt1—N1—C1—C6	−1.9 (6)	C12—N4—C11—C10	−179.5 (5)
C1—N1—C2—C3	0.7 (8)	C14—N3—C11—N4	1.4 (8)
Pt1—N1—C2—C3	−175.2 (4)	Pt1—N3—C11—N4	−175.0 (4)
N1—C2—C3—C4	0.7 (8)	C14—N3—C11—C10	−179.4 (5)
C1—N2—C4—C3	0.7 (8)	Pt1—N3—C11—C10	4.2 (6)
C2—C3—C4—N2	−1.5 (9)	C5—C10—C11—N4	175.7 (5)
N3—Pt1—C5—C10	0.7 (5)	C9—C10—C11—N4	−3.2 (9)
N1—Pt1—C5—C10	−176.3 (5)	C5—C10—C11—N3	−3.6 (7)
Cl3—Pt1—C5—C10	−88.0 (5)	C9—C10—C11—N3	177.5 (6)
Cl2—Pt1—C5—C10	91.4 (5)	C11—N4—C12—C13	−0.9 (9)
Cl1—Pt1—C5—C10	−175 (25)	N4—C12—C13—C14	1.1 (10)
N3—Pt1—C5—C6	178.9 (5)	C11—N3—C14—C13	−1.2 (9)
N1—Pt1—C5—C6	1.9 (4)	Pt1—N3—C14—C13	174.7 (5)
Cl3—Pt1—C5—C6	90.1 (4)	C12—C13—C14—N3	0.0 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···Cl1ⁱ	0.93	2.61	3.330 (6)	135
C4—H4···Cl2ⁱⁱ	0.93	2.84	3.680 (6)	151
C12—H12···Cl3ⁱⁱⁱ	0.93	2.78	3.509 (6)	136

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

Experimental details

Crystal data
Chemical formula	[Pt(C₁₅H₁₁N₄O)Cl₃]·C₂H₃N
M_r	605.77
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.5739 (8), 10.3371 (10), 12.6610 (12)
α, β, γ (°)	68.955 (2), 80.033 (2), 70.619 (2)
V (Å³)	986.09 (16)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	7.54
Crystal size (mm)	0.21 × 0.16 × 0.13

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.346, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	5788, 3666, 3442
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.085, 1.04
No. of reflections	3666
No. of parameters	246
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.63, −1.61

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Pt1—C5	1.944 (5)	Pt1—Cl3	2.3018 (16)
Pt1—N3	2.038 (4)	Pt1—Cl2	2.3528 (15)
Pt1—N1	2.046 (4)	Pt1—Cl1	2.4160 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···Cl1ⁱ	0.93	2.61	3.330 (6)	135.1
C4—H4···Cl2ⁱⁱ	0.93	2.84	3.680 (6)	151.4
C12—H12···Cl3ⁱⁱⁱ	0.93	2.78	3.509 (6)	135.7

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

Acknowledgements

This work was sponsored by the Shanghai Pujiang Program (10PJ1400100).

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