An acetonitrile solvatomorph of di-chlorido-(1,10-phenanthroline-5,6-dione)platinum(II).

In the title complex, [PtCl2(C12H6N2O2)]·CH3CN, the Pt(II) atom lies in a slightly distorted square-planar arrangement defined by an N2Cl2 donor set. In the packed structure, columns of complex moieties are stacked such that the neighboring units are oriented at 180° and laterally displaced with respect to each other. This prevents any overlap of the phenanthroline rings and thus there is no possibility of any π-π inter-actions between aromatic rings.

Related literature

For condensation of the free and complexed phendione ligand with primary amines, see: Dickerson & Summers (1970 ▶); MacDonnell & Bodige (1996 ▶); Moucheron et al. (1997 ▶); Westerlund et al. (2005 ▶); Williams et al. (2012 ▶). For use of the ligand in the construction of multinuclear homo- and heterometallic complexes as well as dendritic polynuclear metal structures, see: Fox et al. (1991 ▶); MacDonnell & Bodige (1996 ▶); Paw & Eisenberg (1997 ▶); Calderazzo et al. (1999 ▶); Campagna et al. (1999 ▶); Calucci et al. (2006 ▶). For anti­microbial activity of the free ligand and the title complex, see: Roy et al. (2008 ▶). For previous structural studies related to the title complex, see: Granger et al. (2005 ▶); Okamura et al. (2006 ▶); Roy et al. (2008 ▶). For synthesis of Pt(DMSO)2Cl2, see: Romeo & Scolaro (1998 ▶).

Experimental

Crystal data

[PtCl2(C12H6N2O2)]·C2H3N

M = 517.23

Monoclinic,

a = 6.7285 (2) Å

b = 22.6380 (6) Å

c = 9.7561 (3) Å

β = 98.0740 (17)°

V = 1471.32 (7) Å3

Z = 4

Mo Kα radiation

μ = 9.91 mm−1

T = 298 K

0.40 × 0.06 × 0.05 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: gaussian (XPREP in SHELXL/PC; Sheldrick, 2008 ▶) T min = 0.174, T max = 0.629

11801 measured reflections

3345 independent reflections

2837 reflections with I > 2σ(I)

R int = 0.081

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.094

S = 1.16

3345 reflections

201 parameters

H-atom parameters constrained

Δρmax = 1.48 e Å−3

Δρmin = −1.30 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: COLLECT; data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997) ▶; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL/PC (Sheldrick, 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S160053681303256X/mw2118sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681303256X/mw2118Isup2.hkl

Additional supporting information: crystallographic information; 3D view; checkCIF report

[PtCl2(C12H6N2O2)]·C2H3N	F(000) = 968
Mr = 517.23	Dx = 2.335 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 6.7285 (2) Å	Cell parameters from 3185 reflections
b = 22.6380 (6) Å	θ = 1.0–27.5°
c = 9.7561 (3) Å	µ = 9.91 mm−1
β = 98.0740 (17)°	T = 298 K
V = 1471.32 (7) Å3	Needle, yellow
Z = 4	0.40 × 0.06 × 0.05 mm

Nonius KappaCCD diffractometer	2837 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.081
φ and ω scans	θmax = 27.5°, θmin = 2.3°
Absorption correction: gaussian (XPREP in SHELXL/PC; Sheldrick, 2008)	h = −7→8
Tmin = 0.174, Tmax = 0.629	k = −29→26
11801 measured reflections	l = −12→9
3345 independent reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039	H-atom parameters constrained
wR(F2) = 0.094	w = 1/[σ2(Fo2) + (0.0216P)2 + 7.4291P] where P = (Fo2 + 2Fc2)/3
S = 1.16	(Δ/σ)max = 0.002
3345 reflections	Δρmax = 1.48 e Å−3
201 parameters	Δρmin = −1.30 e Å−3
0 restraints	Extinction correction: SHELXL2013 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0038 (4)

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.

	x	y	z	Uiso*/Ueq
Pt1	0.22275 (4)	0.538338 (12)	0.35597 (3)	0.03226 (13)
Cl1	0.2456 (3)	0.63727 (10)	0.4031 (2)	0.0535 (5)
Cl2	0.1736 (3)	0.55973 (11)	0.12469 (18)	0.0490 (5)
O1	0.2795 (12)	0.3386 (4)	0.8277 (7)	0.078 (2)
O2	0.2372 (13)	0.2739 (4)	0.5941 (9)	0.088 (2)
N1	0.2643 (8)	0.5130 (3)	0.5574 (5)	0.0332 (13)
C2	0.2906 (10)	0.5475 (4)	0.6672 (8)	0.0413 (18)
H2A	0.2927	0.5882	0.6548	0.050*
C3	0.3157 (11)	0.5248 (4)	0.8018 (8)	0.047 (2)
H3A	0.3346	0.5501	0.8777	0.057*
C4	0.3120 (12)	0.4655 (4)	0.8204 (8)	0.050 (2)
H4A	0.3290	0.4496	0.9093	0.060*
C5	0.2831 (11)	0.4291 (4)	0.7071 (8)	0.0437 (19)
C6	0.2705 (13)	0.3630 (5)	0.7205 (10)	0.060 (3)
C7	0.2476 (13)	0.3264 (5)	0.5856 (10)	0.055 (2)
C8	0.2270 (12)	0.3572 (4)	0.4480 (9)	0.0442 (18)
C9	0.2042 (13)	0.3274 (4)	0.3234 (9)	0.055 (2)
H9A	0.2025	0.2864	0.3205	0.066*
C10	0.1843 (13)	0.3600 (5)	0.2043 (9)	0.056 (2)
H10A	0.1715	0.3409	0.1192	0.067*
C11	0.1828 (11)	0.4203 (4)	0.2087 (8)	0.0428 (18)
H11A	0.1639	0.4414	0.1262	0.051*
N12	0.2080 (8)	0.4498 (3)	0.3291 (6)	0.0339 (13)
C13	0.2300 (10)	0.4186 (4)	0.4489 (7)	0.0342 (15)
C14	0.2592 (11)	0.4543 (3)	0.5756 (7)	0.0335 (16)
N1A	0.328 (2)	0.6730 (6)	−0.1587 (14)	0.109 (4)
C2A	0.2973 (18)	0.6945 (6)	−0.0552 (13)	0.076 (3)
C3A	0.2662 (19)	0.7226 (6)	0.0677 (12)	0.085 (3)
H3A1	0.3414	0.7588	0.0775	0.127*
H3A2	0.3099	0.6972	0.1448	0.127*
H3A3	0.1259	0.7312	0.0650	0.127*

	U11	U22	U33	U12	U13	U23
Pt1	0.03263 (17)	0.03434 (19)	0.03048 (17)	−0.00009 (12)	0.00674 (10)	−0.00010 (11)
Cl1	0.0700 (14)	0.0367 (11)	0.0542 (11)	−0.0022 (10)	0.0102 (9)	−0.0047 (9)
Cl2	0.0597 (12)	0.0558 (13)	0.0317 (9)	−0.0014 (10)	0.0069 (8)	0.0063 (8)
O1	0.095 (5)	0.081 (6)	0.060 (4)	0.013 (4)	0.015 (4)	0.039 (4)
O2	0.127 (7)	0.042 (5)	0.094 (6)	0.005 (4)	0.018 (5)	0.027 (4)
N1	0.024 (3)	0.048 (4)	0.029 (3)	−0.003 (3)	0.006 (2)	−0.001 (3)
C2	0.033 (4)	0.051 (5)	0.041 (4)	−0.002 (3)	0.010 (3)	−0.007 (3)
C3	0.041 (4)	0.071 (7)	0.030 (4)	0.003 (4)	0.009 (3)	−0.010 (4)
C4	0.040 (4)	0.076 (7)	0.034 (4)	0.006 (4)	0.006 (3)	0.009 (4)
C5	0.031 (4)	0.062 (6)	0.039 (4)	0.005 (4)	0.008 (3)	0.007 (4)
C6	0.050 (5)	0.074 (7)	0.057 (5)	0.012 (5)	0.009 (4)	0.024 (5)
C7	0.056 (5)	0.050 (6)	0.060 (5)	0.007 (4)	0.017 (4)	0.018 (4)
C8	0.045 (4)	0.030 (4)	0.058 (5)	0.009 (3)	0.009 (3)	0.008 (3)
C9	0.068 (6)	0.036 (5)	0.063 (5)	−0.002 (4)	0.012 (4)	−0.010 (4)
C10	0.061 (5)	0.056 (6)	0.051 (5)	−0.003 (5)	0.010 (4)	−0.015 (4)
C11	0.042 (4)	0.044 (5)	0.042 (4)	−0.005 (4)	0.007 (3)	−0.009 (3)
N12	0.035 (3)	0.037 (4)	0.031 (3)	0.001 (3)	0.007 (2)	−0.001 (2)
C13	0.028 (3)	0.040 (4)	0.035 (3)	0.002 (3)	0.005 (3)	−0.003 (3)
C14	0.033 (3)	0.037 (4)	0.033 (3)	0.000 (3)	0.005 (3)	0.001 (3)
N1A	0.131 (10)	0.094 (10)	0.105 (9)	−0.019 (8)	0.023 (7)	−0.019 (7)
C2A	0.090 (8)	0.056 (7)	0.086 (8)	−0.001 (6)	0.021 (6)	0.003 (6)
C3A	0.106 (9)	0.074 (9)	0.076 (8)	0.006 (7)	0.019 (6)	0.010 (6)

Pt1—N12	2.022 (7)	C7—C8	1.503 (12)
Pt1—N1	2.028 (5)	C8—C9	1.380 (12)
Pt1—Cl2	2.2860 (18)	C8—C13	1.389 (11)
Pt1—Cl1	2.287 (2)	C9—C10	1.367 (13)
O1—C6	1.177 (11)	C9—H9A	0.9300
O2—C7	1.192 (13)	C10—C11	1.365 (13)
N1—C2	1.318 (10)	C10—H10A	0.9300
N1—C14	1.341 (10)	C11—N12	1.341 (9)
C2—C3	1.398 (11)	C11—H11A	0.9300
C2—H2A	0.9300	N12—C13	1.356 (9)
C3—C4	1.356 (13)	C13—C14	1.466 (10)
C3—H3A	0.9300	N1A—C2A	1.166 (16)
C4—C5	1.370 (12)	C2A—C3A	1.399 (17)
C4—H4A	0.9300	C3A—H3A1	0.9600
C5—C14	1.395 (11)	C3A—H3A2	0.9600
C5—C6	1.506 (14)	C3A—H3A3	0.9600
C6—C7	1.545 (15)
N12—Pt1—N1	81.0 (2)	C9—C8—C7	123.0 (8)
N12—Pt1—Cl2	94.83 (17)	C13—C8—C7	117.4 (8)
N1—Pt1—Cl2	175.8 (2)	C10—C9—C8	118.1 (9)
N12—Pt1—Cl1	175.87 (16)	C10—C9—H9A	121.0
N1—Pt1—Cl1	94.9 (2)	C8—C9—H9A	121.0
Cl2—Pt1—Cl1	89.27 (8)	C11—C10—C9	120.8 (8)
C2—N1—C14	118.9 (7)	C11—C10—H10A	119.6
C2—N1—Pt1	127.2 (6)	C9—C10—H10A	119.6
C14—N1—Pt1	113.8 (5)	N12—C11—C10	121.6 (8)
N1—C2—C3	122.0 (9)	N12—C11—H11A	119.2
N1—C2—H2A	119.0	C10—C11—H11A	119.2
C3—C2—H2A	119.0	C11—N12—C13	118.7 (7)
C4—C3—C2	119.2 (8)	C11—N12—Pt1	127.2 (5)
C4—C3—H3A	120.4	C13—N12—Pt1	114.0 (5)
C2—C3—H3A	120.4	N12—C13—C8	121.1 (7)
C3—C4—C5	119.4 (8)	N12—C13—C14	115.0 (7)
C3—C4—H4A	120.3	C8—C13—C14	123.9 (7)
C5—C4—H4A	120.3	N1—C14—C5	121.6 (7)
C4—C5—C14	118.9 (8)	N1—C14—C13	116.1 (6)
C4—C5—C6	122.0 (8)	C5—C14—C13	122.3 (7)
C14—C5—C6	119.1 (8)	N1A—C2A—C3A	177.3 (14)
O1—C6—C5	123.2 (10)	C2A—C3A—H3A1	109.5
O1—C6—C7	119.4 (11)	C2A—C3A—H3A2	109.5
C5—C6—C7	117.4 (7)	H3A1—C3A—H3A2	109.5
O2—C7—C8	121.7 (10)	C2A—C3A—H3A3	109.5
O2—C7—C6	118.4 (9)	H3A1—C3A—H3A3	109.5
C8—C7—C6	119.8 (9)	H3A2—C3A—H3A3	109.5
C9—C8—C13	119.6 (8)
N12—Pt1—N1—C2	−179.6 (6)	C10—C11—N12—C13	−1.8 (11)
Cl1—Pt1—N1—C2	0.9 (6)	C10—C11—N12—Pt1	177.0 (6)
N12—Pt1—N1—C14	−1.0 (5)	N1—Pt1—N12—C11	−178.5 (6)
Cl1—Pt1—N1—C14	179.4 (4)	Cl2—Pt1—N12—C11	1.6 (6)
C14—N1—C2—C3	0.8 (10)	N1—Pt1—N12—C13	0.3 (5)
Pt1—N1—C2—C3	179.3 (5)	Cl2—Pt1—N12—C13	−179.6 (4)
N1—C2—C3—C4	−0.3 (11)	C11—N12—C13—C8	0.1 (10)
C2—C3—C4—C5	−0.3 (12)	Pt1—N12—C13—C8	−178.9 (5)
C3—C4—C5—C14	0.3 (12)	C11—N12—C13—C14	179.3 (6)
C3—C4—C5—C6	−177.9 (7)	Pt1—N12—C13—C14	0.4 (7)
C4—C5—C6—O1	2.0 (13)	C9—C8—C13—N12	1.0 (11)
C14—C5—C6—O1	−176.2 (8)	C7—C8—C13—N12	−178.6 (7)
C4—C5—C6—C7	−177.2 (7)	C9—C8—C13—C14	−178.2 (7)
C14—C5—C6—C7	4.6 (11)	C7—C8—C13—C14	2.2 (11)
O1—C6—C7—O2	0.9 (14)	C2—N1—C14—C5	−0.8 (10)
C5—C6—C7—O2	−179.9 (9)	Pt1—N1—C14—C5	−179.4 (5)
O1—C6—C7—C8	177.3 (8)	C2—N1—C14—C13	−179.8 (6)
C5—C6—C7—C8	−3.5 (12)	Pt1—N1—C14—C13	1.5 (7)
O2—C7—C8—C9	−3.1 (14)	C4—C5—C14—N1	0.2 (11)
C6—C7—C8—C9	−179.4 (8)	C6—C5—C14—N1	178.5 (7)
O2—C7—C8—C13	176.5 (9)	C4—C5—C14—C13	179.2 (7)
C6—C7—C8—C13	0.1 (11)	C6—C5—C14—C13	−2.6 (11)
C13—C8—C9—C10	−0.4 (12)	N12—C13—C14—N1	−1.3 (9)
C7—C8—C9—C10	179.2 (8)	C8—C13—C14—N1	178.0 (7)
C8—C9—C10—C11	−1.3 (13)	N12—C13—C14—C5	179.7 (6)
C9—C10—C11—N12	2.4 (13)	C8—C13—C14—C5	−1.1 (11)