Chlorido[1,1'-(5-methyl-1,3-phenyl-ene)bis-(3,5-dimethyl-1H-imidazol-2-yl-idene)]platinum(II).

In the title compound, [Pt(C17H19N4)Cl], the Pt(II) cation is C,C',C''-chelated by the 1,1'-(5-methyl-1,3-phenyl-ene)bis-(3,5-dimethyl-1H-imidazolyl-idene) anion and coordinated by a Cl(-) anion in a distorted square-planar coordination geometry. π-π stacking is observed between nearly parallel imidazole and benzene rings of adjacent mol-ecules, the centroid-centroid distance being 3.802 (4) Å.

Related literature

For the application of PtII complexes in organic light-emitting diodes, see: Yang et al. (2008 ▶); Bakken et al. (2012 ▶); Fleetham et al. (2012 ▶). For a related compound, see: Wang et al. (2010 ▶).

Experimental

Crystal data

[Pt(C17H19N4)Cl]

M = 509.90

Monoclinic,

a = 11.042 (5) Å

b = 14.552 (6) Å

c = 11.524 (5) Å

β = 116.049 (4)°

V = 1663.6 (12) Å3

Z = 4

Mo Kα radiation

μ = 8.60 mm−1

T = 296 K

0.16 × 0.13 × 0.07 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.340, T max = 0.584

8411 measured reflections

2958 independent reflections

2579 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.080

S = 1.07

2958 reflections

189 parameters

H-atom parameters constrained

Δρmax = 1.78 e Å−3

Δρmin = −2.04 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813006545/xu5680sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813006545/xu5680Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Pt(C17H19N4)Cl]	F(000) = 976
Mr = 509.90	Dx = 2.036 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4377 reflections
a = 11.042 (5) Å	θ = 2.4–27.5°
b = 14.552 (6) Å	µ = 8.60 mm−1
c = 11.524 (5) Å	T = 296 K
β = 116.049 (4)°	Block, colorless
V = 1663.6 (12) Å3	0.16 × 0.13 × 0.07 mm
Z = 4

Bruker APEXII CCD diffractometer	2958 independent reflections
Radiation source: fine-focus sealed tube	2579 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
Detector resolution: 10 pixels mm-1	θmax = 25.0°, θmin = 2.1°
φ and ω scans	h = −12→13
Absorption correction: multi-scan (SADABS; Bruker, 2001)	k = −16→17
Tmin = 0.340, Tmax = 0.584	l = −12→13
8411 measured reflections

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0412P)2 + 5.3708P] where P = (Fo2 + 2Fc2)/3
2958 reflections	(Δ/σ)max = 0.001
189 parameters	Δρmax = 1.78 e Å−3
0 restraints	Δρmin = −2.04 e Å−3

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.

	x	y	z	Uiso*/Ueq
Pt1	0.48107 (2)	0.137708 (16)	0.63220 (2)	0.02999 (11)
C1	0.6140 (6)	0.1354 (4)	0.5684 (6)	0.0310 (14)
C2	0.6974 (6)	0.0590 (4)	0.5917 (6)	0.0296 (13)
C3	0.7964 (6)	0.0559 (4)	0.5471 (6)	0.0345 (14)
H3	0.8522	0.0049	0.5631	0.041*
C4	0.8098 (7)	0.1319 (4)	0.4772 (7)	0.0390 (16)
C5	0.7255 (6)	0.2074 (4)	0.4513 (6)	0.0335 (14)
H5	0.7340	0.2566	0.4039	0.040*
C6	0.6260 (6)	0.2085 (4)	0.4978 (6)	0.0287 (13)
C7	0.5042 (7)	0.3599 (4)	0.4217 (7)	0.0387 (16)
C8	0.3955 (7)	0.3958 (5)	0.4341 (7)	0.0450 (17)
H8	0.3540	0.4519	0.4023	0.054*
C9	0.4420 (6)	0.2595 (4)	0.5339 (6)	0.0340 (7)
C10	0.5694 (6)	0.0138 (4)	0.7018 (6)	0.0362 (7)
C11	0.6528 (8)	−0.1257 (5)	0.7757 (7)	0.0462 (18)
H11	0.6655	−0.1825	0.8164	0.055*
C12	0.7198 (7)	−0.0930 (4)	0.7090 (6)	0.0362 (14)
C13	0.9173 (9)	0.1298 (6)	0.4307 (10)	0.060 (2)
H13A	0.9079	0.1825	0.3773	0.091*
H13B	0.9082	0.0749	0.3815	0.091*
H13C	1.0045	0.1308	0.5035	0.091*
C14	0.2445 (8)	0.3377 (6)	0.5408 (9)	0.056 (2)
H14A	0.1713	0.2998	0.4838	0.084*
H14B	0.2146	0.4003	0.5341	0.084*
H14C	0.2744	0.3167	0.6281	0.084*
C15	0.5829 (8)	0.4025 (5)	0.3576 (8)	0.053 (2)
H15A	0.6767	0.4044	0.4175	0.080*
H15B	0.5510	0.4639	0.3308	0.080*
H15C	0.5714	0.3667	0.2836	0.080*
C16	0.4651 (9)	−0.0611 (6)	0.8318 (8)	0.057 (2)
H16A	0.4607	−0.0018	0.8661	0.085*
H16B	0.4962	−0.1056	0.9003	0.085*
H16C	0.3771	−0.0783	0.7677	0.085*
C17	0.8297 (8)	−0.1388 (4)	0.6863 (8)	0.0439 (17)
H17A	0.8081	−0.1359	0.5961	0.066*
H17B	0.8375	−0.2019	0.7130	0.066*
H17C	0.9136	−0.1078	0.7353	0.066*
Cl1	0.3130 (2)	0.14031 (13)	0.7148 (2)	0.0560 (5)
N1	0.5316 (5)	0.2784 (4)	0.4818 (5)	0.0340 (7)
N2	0.3591 (5)	0.3319 (4)	0.5039 (5)	0.0340 (7)
N3	0.6696 (5)	−0.0091 (4)	0.6648 (5)	0.0362 (7)
N4	0.5613 (5)	−0.0576 (4)	0.7712 (5)	0.0362 (7)

	U11	U22	U33	U12	U13	U23
Pt1	0.02833 (16)	0.03514 (16)	0.03016 (16)	−0.00059 (10)	0.01622 (11)	−0.00590 (10)
C1	0.025 (3)	0.035 (3)	0.033 (3)	0.000 (3)	0.013 (3)	−0.007 (3)
C2	0.032 (3)	0.027 (3)	0.029 (3)	0.003 (3)	0.013 (3)	0.000 (2)
C3	0.032 (3)	0.036 (3)	0.037 (4)	0.008 (3)	0.017 (3)	0.003 (3)
C4	0.034 (4)	0.048 (4)	0.041 (4)	0.007 (3)	0.021 (3)	0.002 (3)
C5	0.035 (3)	0.033 (3)	0.035 (3)	0.002 (3)	0.018 (3)	0.004 (3)
C6	0.031 (3)	0.026 (3)	0.027 (3)	0.005 (2)	0.012 (3)	−0.001 (2)
C7	0.041 (4)	0.039 (4)	0.035 (4)	0.004 (3)	0.016 (3)	0.002 (3)
C8	0.048 (4)	0.038 (4)	0.049 (4)	0.014 (3)	0.022 (4)	0.004 (3)
C9	0.0303 (17)	0.0384 (17)	0.0344 (18)	0.0063 (14)	0.0151 (14)	−0.0035 (14)
C10	0.0376 (18)	0.0386 (18)	0.0329 (18)	−0.0016 (15)	0.0159 (15)	−0.0006 (14)
C11	0.051 (4)	0.041 (4)	0.039 (4)	0.000 (3)	0.012 (4)	0.008 (3)
C12	0.040 (4)	0.032 (3)	0.030 (3)	0.002 (3)	0.009 (3)	0.001 (3)
C13	0.053 (5)	0.069 (6)	0.081 (6)	0.021 (4)	0.050 (5)	0.019 (4)
C14	0.052 (5)	0.061 (5)	0.064 (5)	0.024 (4)	0.033 (4)	0.002 (4)
C15	0.067 (5)	0.046 (4)	0.062 (5)	0.017 (4)	0.042 (4)	0.024 (4)
C16	0.071 (5)	0.067 (5)	0.044 (4)	−0.012 (4)	0.036 (4)	0.001 (4)
C17	0.045 (4)	0.038 (4)	0.048 (4)	0.003 (3)	0.019 (4)	0.003 (3)
Cl1	0.0584 (12)	0.0608 (12)	0.0749 (14)	0.0069 (9)	0.0531 (12)	−0.0027 (9)
N1	0.0303 (17)	0.0384 (17)	0.0344 (18)	0.0063 (14)	0.0151 (14)	−0.0035 (14)
N2	0.0303 (17)	0.0384 (17)	0.0344 (18)	0.0063 (14)	0.0151 (14)	−0.0035 (14)
N3	0.0376 (18)	0.0386 (18)	0.0329 (18)	−0.0016 (15)	0.0159 (15)	−0.0006 (14)
N4	0.0376 (18)	0.0386 (18)	0.0329 (18)	−0.0016 (15)	0.0159 (15)	−0.0006 (14)

Pt1—C1	1.909 (6)	C10—N3	1.389 (8)
Pt1—C9	2.045 (6)	C11—C12	1.366 (10)
Pt1—C10	2.040 (6)	C11—N4	1.400 (9)
Pt1—Cl1	2.4295 (19)	C11—H11	0.9300
C1—C6	1.380 (8)	C12—N3	1.345 (8)
C1—C2	1.392 (8)	C12—C17	1.504 (10)
C2—C3	1.398 (8)	C13—H13A	0.9600
C2—N3	1.419 (8)	C13—H13B	0.9600
C3—C4	1.414 (9)	C13—H13C	0.9600
C3—H3	0.9300	C14—N2	1.504 (9)
C4—C5	1.385 (9)	C14—H14A	0.9600
C4—C13	1.502 (10)	C14—H14B	0.9600
C5—C6	1.419 (8)	C14—H14C	0.9600
C5—H5	0.9300	C15—H15A	0.9600
C6—N1	1.409 (7)	C15—H15B	0.9600
C7—N1	1.339 (8)	C15—H15C	0.9600
C7—C8	1.372 (10)	C16—N4	1.507 (9)
C7—C15	1.499 (10)	C16—H16A	0.9600
C8—N2	1.399 (9)	C16—H16B	0.9600
C8—H8	0.9300	C16—H16C	0.9600
C9—N2	1.337 (8)	C17—H17A	0.9600
C9—N1	1.393 (8)	C17—H17B	0.9600
C10—N4	1.338 (8)	C17—H17C	0.9600
C1—Pt1—C10	79.6 (3)	C4—C13—H13A	109.5
C1—Pt1—C9	79.2 (2)	C4—C13—H13B	109.5
C10—Pt1—C9	158.8 (2)	H13A—C13—H13B	109.5
C1—Pt1—Cl1	179.6 (2)	C4—C13—H13C	109.5
C10—Pt1—Cl1	100.12 (18)	H13A—C13—H13C	109.5
C9—Pt1—Cl1	101.06 (17)	H13B—C13—H13C	109.5
C6—C1—C2	120.2 (6)	N2—C14—H14A	109.5
C6—C1—Pt1	120.1 (4)	N2—C14—H14B	109.5
C2—C1—Pt1	119.6 (5)	H14A—C14—H14B	109.5
C1—C2—C3	120.9 (6)	N2—C14—H14C	109.5
C1—C2—N3	112.1 (5)	H14A—C14—H14C	109.5
C3—C2—N3	127.1 (5)	H14B—C14—H14C	109.5
C2—C3—C4	118.5 (6)	C7—C15—H15A	109.5
C2—C3—H3	120.7	C7—C15—H15B	109.5
C4—C3—H3	120.7	H15A—C15—H15B	109.5
C5—C4—C3	121.0 (6)	C7—C15—H15C	109.5
C5—C4—C13	120.0 (6)	H15A—C15—H15C	109.5
C3—C4—C13	119.0 (6)	H15B—C15—H15C	109.5
C4—C5—C6	119.1 (6)	N4—C16—H16A	109.5
C4—C5—H5	120.4	N4—C16—H16B	109.5
C6—C5—H5	120.4	H16A—C16—H16B	109.5
C1—C6—N1	112.2 (5)	N4—C16—H16C	109.5
C1—C6—C5	120.2 (5)	H16A—C16—H16C	109.5
N1—C6—C5	127.6 (5)	H16B—C16—H16C	109.5
N1—C7—C8	107.0 (6)	C12—C17—H17A	109.5
N1—C7—C15	124.9 (6)	C12—C17—H17B	109.5
C8—C7—C15	128.1 (6)	H17A—C17—H17B	109.5
C7—C8—N2	107.0 (6)	C12—C17—H17C	109.5
C7—C8—H8	126.5	H17A—C17—H17C	109.5
N2—C8—H8	126.5	H17B—C17—H17C	109.5
N2—C9—N1	105.5 (5)	C7—N1—C9	110.9 (5)
N2—C9—Pt1	141.3 (5)	C7—N1—C6	133.9 (6)
N1—C9—Pt1	113.2 (4)	C9—N1—C6	115.1 (5)
N4—C10—N3	105.6 (5)	C9—N2—C8	109.6 (5)
N4—C10—Pt1	140.8 (5)	C9—N2—C14	122.4 (6)
N3—C10—Pt1	113.5 (4)	C8—N2—C14	128.0 (6)
C12—C11—N4	107.0 (6)	C12—N3—C10	110.7 (5)
C12—C11—H11	126.5	C12—N3—C2	134.3 (5)
N4—C11—H11	126.5	C10—N3—C2	115.1 (5)
N3—C12—C11	107.1 (6)	C10—N4—C11	109.6 (6)
N3—C12—C17	124.5 (6)	C10—N4—C16	123.4 (6)
C11—C12—C17	128.4 (6)	C11—N4—C16	127.0 (6)

Table 1

Selected bond lengths (Å)

Pt1—C1	1.909 (6)
Pt1—C9	2.045 (6)
Pt1—C10	2.040 (6)
Pt1—Cl1	2.4295 (19)