Trichlorido[4-meth-oxy-2,6-bis-(2-pyrimidin-2-yl-κN)phenyl-κC(1)]platinum(IV) acetonitrile monosolvate.

In the title complex, [Pt(C(15)H(11)N(4)O)Cl(3)]·CH(3)CN, the Pt(IV) ion adopts a distorted octa-hedral coordination geometry defined by a tridentate cyclo-metalated NCN ligand and three Cl atoms. In the crystal, individual mol-ecules are aggregated into a three-dimensional network by C-H⋯Cl hydrogen-bonding inter-actions and π-π stacking inter-actions 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 PtII complexes with tridentate NCN ligands, see: Kozhevnikov et al. (2008 ▶); Tam et al. (2011 ▶). For Pt—Cl bond lengths in other PtIV 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 = 605.77

Triclinic,

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[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.085

S = 1.04

3666 reflections

246 parameters

H-atom parameters constrained

Δρmax = 1.63 e Å−3

Δρmin = −1.61 e Å−3

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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812036410/hp2041sup1.cif

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

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

[Pt(C15H11N4O)Cl3]·C2H3N	Z = 2
Mr = 605.77	F(000) = 576
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0539P)2] where P = (Fo2 + 2Fc2)/3
3666 reflections	(Δ/σ)max = 0.002
246 parameters	Δρmax = 1.63 e Å−3
0 restraints	Δρmin = −1.61 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	0.69455 (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)

	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)

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)

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

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) ; (ii) ; (iii) .