(2,2'-Bipyrimidine-κ(2)N(1),N(1'))bis-(thio-cyanato-κN)platinum(II).

In the title complex, [Pt(NCS)(2)(C(8)H(6)N(4))], the Pt(II) ion is four-coordinated in a distorted square-planar environment defined by two pyrimidine N atoms derived from a chelating 2,2'-bipyrimidine (bpym) ligand and two mutually cis N atoms from two SCN(-) anions. The thio-cyanate ligands are almost linear, displaying N-C-S bond angles of 178.6 (11) and 173.7 (11)°, and the N atoms are slightly bent coordinated to the Pt atom with Pt-N-C bond angles of 172.7 (9) and 160.4 (10)°. In the crystal, mol-ecules are held together by C-H⋯S hydrogen bonds. Intra-molecular C-H⋯N hydrogen bonds are also observed.

Related literature

For the crystal structures of related PtII complexes [PtX 2(bpym)] (X = Cl, I or Br), see: Kaim et al. (2002 ▶); Ha (2010 ▶, 2011 ▶).

Experimental

Crystal data

[Pt(NCS)2(C8H6N4)]

M = 469.42

Monoclinic,

a = 11.0871 (8) Å

b = 9.8779 (7) Å

c = 12.8790 (9) Å

β = 115.135 (1)°

V = 1276.91 (16) Å3

Z = 4

Mo Kα radiation

μ = 11.31 mm−1

T = 200 K

0.34 × 0.28 × 0.28 mm

Data collection

Bruker SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.680, T max = 1.000

7611 measured reflections

2467 independent reflections

2179 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.105

S = 1.09

2467 reflections

172 parameters

H-atom parameters constrained

Δρmax = 4.86 e Å−3

Δρmin = −1.72 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: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812017552/bt5882sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812017552/bt5882Isup2.hkl

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

[Pt(NCS)2(C8H6N4)]	F(000) = 872
Mr = 469.42	Dx = 2.442 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5056 reflections
a = 11.0871 (8) Å	θ = 2.7–26.0°
b = 9.8779 (7) Å	µ = 11.31 mm−1
c = 12.8790 (9) Å	T = 200 K
β = 115.135 (1)°	Block, orange
V = 1276.91 (16) Å3	0.34 × 0.28 × 0.28 mm
Z = 4

Bruker SMART 1000 CCD diffractometer	2467 independent reflections
Radiation source: fine-focus sealed tube	2179 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
φ and ω scans	θmax = 26.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −13→13
Tmin = 0.680, Tmax = 1.000	k = −12→11
7611 measured reflections	l = −15→12

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.030P)2 + 21.4936P] where P = (Fo2 + 2Fc2)/3
2467 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 4.86 e Å−3
0 restraints	Δρmin = −1.72 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	0.16191 (4)	0.40380 (4)	0.58301 (3)	0.04005 (15)
S1	−0.0058 (3)	0.6087 (4)	0.8261 (3)	0.0601 (8)
S2	0.0260 (3)	−0.0068 (3)	0.6854 (3)	0.0519 (7)
N1	0.2144 (8)	0.5882 (9)	0.5497 (7)	0.0382 (18)
N2	0.3270 (10)	0.6962 (9)	0.4524 (8)	0.050 (2)
N3	0.3600 (10)	0.4377 (10)	0.3743 (8)	0.049 (2)
N4	0.2425 (8)	0.3496 (9)	0.4767 (7)	0.0385 (18)
N5	0.0853 (9)	0.4748 (10)	0.6838 (8)	0.048 (2)
N6	0.1173 (10)	0.2136 (11)	0.6120 (8)	0.058 (3)
C1	0.1920 (10)	0.7047 (11)	0.5879 (8)	0.042 (2)
H1	0.1456	0.7078	0.6352	0.051*
C2	0.2375 (11)	0.8237 (12)	0.5579 (9)	0.048 (3)
H2	0.2214	0.9091	0.5835	0.057*
C3	0.3061 (12)	0.8148 (11)	0.4906 (9)	0.049 (3)
H3	0.3390	0.8950	0.4711	0.059*
C4	0.2822 (10)	0.5887 (11)	0.4827 (8)	0.041 (2)
C5	0.2989 (10)	0.4514 (11)	0.4419 (9)	0.041 (2)
C6	0.3601 (12)	0.3115 (12)	0.3349 (10)	0.054 (3)
H6	0.4017	0.2973	0.2848	0.064*
C7	0.3040 (13)	0.2034 (12)	0.3627 (10)	0.055 (3)
H7	0.3042	0.1161	0.3317	0.066*
C8	0.2465 (11)	0.2250 (11)	0.4376 (9)	0.047 (2)
H8	0.2097	0.1511	0.4615	0.056*
C9	0.0462 (10)	0.5294 (12)	0.7422 (9)	0.046 (3)
C10	0.0757 (10)	0.1268 (10)	0.6445 (9)	0.038 (2)

	U11	U22	U33	U12	U13	U23
Pt1	0.0392 (2)	0.0493 (3)	0.0308 (2)	−0.00470 (17)	0.01392 (16)	0.00473 (17)
S1	0.0539 (17)	0.082 (2)	0.0512 (17)	0.0017 (16)	0.0284 (14)	−0.0038 (16)
S2	0.0481 (15)	0.0567 (17)	0.0519 (16)	−0.0078 (13)	0.0222 (13)	0.0038 (13)
N1	0.035 (4)	0.052 (5)	0.025 (4)	0.000 (4)	0.010 (3)	0.002 (4)
N2	0.068 (6)	0.040 (5)	0.051 (5)	−0.003 (4)	0.034 (5)	0.000 (4)
N3	0.059 (6)	0.050 (6)	0.047 (5)	−0.002 (4)	0.030 (5)	−0.001 (4)
N4	0.041 (4)	0.043 (5)	0.030 (4)	−0.005 (4)	0.014 (4)	0.002 (4)
N5	0.052 (5)	0.058 (6)	0.040 (5)	−0.004 (5)	0.025 (4)	−0.007 (4)
N6	0.062 (6)	0.072 (7)	0.039 (5)	−0.018 (5)	0.020 (5)	0.003 (5)
C1	0.046 (6)	0.045 (6)	0.032 (5)	0.003 (5)	0.013 (4)	−0.009 (4)
C2	0.049 (6)	0.056 (7)	0.032 (5)	0.002 (5)	0.012 (5)	−0.008 (5)
C3	0.062 (7)	0.043 (6)	0.047 (6)	−0.012 (5)	0.028 (5)	−0.007 (5)
C4	0.036 (5)	0.055 (6)	0.029 (5)	−0.003 (5)	0.011 (4)	0.004 (4)
C5	0.040 (5)	0.043 (6)	0.040 (6)	−0.005 (4)	0.016 (5)	0.000 (4)
C6	0.066 (7)	0.050 (7)	0.052 (7)	0.003 (6)	0.032 (6)	−0.005 (5)
C7	0.072 (8)	0.044 (6)	0.047 (6)	0.008 (6)	0.021 (6)	−0.002 (5)
C8	0.053 (6)	0.043 (6)	0.043 (6)	−0.007 (5)	0.019 (5)	−0.002 (5)
C9	0.043 (6)	0.048 (6)	0.041 (6)	−0.006 (5)	0.011 (5)	0.009 (5)
C10	0.048 (6)	0.028 (5)	0.041 (5)	−0.006 (4)	0.023 (5)	0.001 (4)

Pt1—N1	2.014 (9)	N5—C9	1.151 (14)
Pt1—N4	1.999 (8)	N6—C10	1.135 (13)
Pt1—N5	1.958 (9)	C1—C2	1.397 (16)
Pt1—N6	2.017 (11)	C1—H1	0.9500
S1—C9	1.625 (13)	C2—C3	1.378 (15)
S2—C10	1.602 (10)	C2—H2	0.9500
N1—C1	1.316 (13)	C3—H3	0.9500
N1—C4	1.363 (13)	C4—C5	1.494 (15)
N2—C4	1.301 (13)	C6—C7	1.359 (17)
N2—C3	1.328 (14)	C6—H6	0.9500
N3—C5	1.318 (14)	C7—C8	1.380 (16)
N3—C6	1.346 (14)	C7—H7	0.9500
N4—C8	1.338 (13)	C8—H8	0.9500
N4—C5	1.357 (13)
N5—Pt1—N4	174.5 (4)	C1—C2—H2	120.6
N5—Pt1—N1	93.6 (4)	N2—C3—C2	121.3 (11)
N4—Pt1—N1	80.9 (3)	N2—C3—H3	119.4
N5—Pt1—N6	90.1 (4)	C2—C3—H3	119.4
N4—Pt1—N6	95.4 (4)	N2—C4—N1	125.1 (10)
N1—Pt1—N6	176.2 (4)	N2—C4—C5	121.0 (9)
C1—N1—C4	118.5 (9)	N1—C4—C5	113.8 (9)
C1—N1—Pt1	126.4 (7)	N3—C5—N4	125.5 (10)
C4—N1—Pt1	115.1 (7)	N3—C5—C4	120.1 (9)
C4—N2—C3	117.4 (9)	N4—C5—C4	114.4 (9)
C5—N3—C6	115.3 (10)	N3—C6—C7	123.7 (11)
C8—N4—C5	117.6 (9)	N3—C6—H6	118.1
C8—N4—Pt1	126.9 (7)	C7—C6—H6	118.1
C5—N4—Pt1	115.5 (7)	C6—C7—C8	117.5 (11)
C9—N5—Pt1	172.7 (9)	C6—C7—H7	121.3
C10—N6—Pt1	160.4 (10)	C8—C7—H7	121.3
N1—C1—C2	118.9 (10)	N4—C8—C7	120.3 (10)
N1—C1—H1	120.5	N4—C8—H8	119.8
C2—C1—H1	120.5	C7—C8—H8	119.8
C3—C2—C1	118.8 (10)	N5—C9—S1	178.6 (11)
C3—C2—H2	120.6	N6—C10—S2	173.7 (11)
N5—Pt1—N1—C1	−1.9 (8)	Pt1—N1—C4—N2	−178.9 (8)
N4—Pt1—N1—C1	177.6 (9)	C1—N1—C4—C5	−178.5 (8)
N5—Pt1—N1—C4	176.6 (7)	Pt1—N1—C4—C5	2.8 (10)
N4—Pt1—N1—C4	−3.9 (7)	C6—N3—C5—N4	2.6 (16)
N1—Pt1—N4—C8	−175.8 (9)	C6—N3—C5—C4	−174.8 (10)
N6—Pt1—N4—C8	5.2 (9)	C8—N4—C5—N3	−1.5 (16)
N1—Pt1—N4—C5	4.4 (7)	Pt1—N4—C5—N3	178.3 (9)
N6—Pt1—N4—C5	−174.5 (7)	C8—N4—C5—C4	176.0 (9)
N5—Pt1—N6—C10	5 (3)	Pt1—N4—C5—C4	−4.2 (11)
N4—Pt1—N6—C10	−174 (3)	N2—C4—C5—N3	0.2 (16)
C4—N1—C1—C2	0.4 (14)	N1—C4—C5—N3	178.5 (9)
Pt1—N1—C1—C2	178.9 (7)	N2—C4—C5—N4	−177.5 (9)
N1—C1—C2—C3	−0.9 (15)	N1—C4—C5—N4	0.9 (13)
C4—N2—C3—C2	−1.2 (17)	C5—N3—C6—C7	−1.1 (18)
C1—C2—C3—N2	1.3 (17)	N3—C6—C7—C8	−1.4 (19)
C3—N2—C4—N1	0.7 (16)	C5—N4—C8—C7	−1.3 (15)
C3—N2—C4—C5	178.8 (10)	Pt1—N4—C8—C7	178.9 (8)
C1—N1—C4—N2	−0.3 (15)	C6—C7—C8—N4	2.6 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···N5	0.95	2.55	3.053 (15)	114
C8—H8···N6	0.95	2.62	3.138 (15)	115
C8—H8···S2i	0.95	2.87	3.496 (11)	124

Table 1

Selected bond lengths (Å)

Pt1—N1	2.014 (9)
Pt1—N4	1.999 (8)
Pt1—N5	1.958 (9)
Pt1—N6	2.017 (11)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯N5	0.95	2.55	3.053 (15)	114
C8—H8⋯N6	0.95	2.62	3.138 (15)	115
C8—H8⋯S2i	0.95	2.87	3.496 (11)	124

Symmetry code: (i) .