3,3'-{Ethane-1,2-diylbis[carbonylbis(azanediyl)]}dipyridinium tetra-chloridoplatinate(II).

In the crystal structure of the title compound, (C(14)H(18)N(6)O(2))·[PtCl(4)], the cation and square-planar anion are located on special positions (on a twofold axis and an inversion centre, respectively). In the crystal structure, N-H⋯Cl hydrogen bonds lead to a staircase-like motif. The central ethane backbone of the cation is disordered over two positions of equal occupancy.

Related literature

For organic–inorganic hybrid compounds displaying N—H⋯Cl—metal hydrogen bonds, see: Adams et al. (2007 ▶); Deifela & Cahill (2009 ▶). Orpen et al. (2004 ▶); Krishna Kumar et al. (2005 ▶, 2006 ▶).

Experimental

Crystal data

(C14H18N6O2)[PtCl4]

M = 639.23

Monoclinic,

a = 17.8126 (13) Å

b = 7.0799 (5) Å

c = 15.5765 (12) Å

β = 103.332 (1)°

V = 1911.4 (2) Å3

Z = 4

Mo Kα radiation

μ = 7.92 mm−1

T = 100 K

0.22 × 0.14 × 0.05 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2006 ▶) T min = 0.275, T max = 0.693

7045 measured reflections

1877 independent reflections

1693 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.064

S = 0.97

1877 reflections

132 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.51 e Å−3

Δρmin = −0.89 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: APEX2 and SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶) and ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97, publCIF (Westrip, 2010 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810004253/bt5171sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810004253/bt5171Isup2.hkl

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

(C14H18N6O2)[PtCl4]	F(000) = 1224
Mr = 639.23	Dx = 2.221 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 17.8126 (13) Å	Cell parameters from 566 reflections
b = 7.0799 (5) Å	θ = 2.4–27.8°
c = 15.5765 (12) Å	µ = 7.92 mm−1
β = 103.332 (1)°	T = 100 K
V = 1911.4 (2) Å3	Plate, yellow
Z = 4	0.22 × 0.14 × 0.05 mm

Bruker APEXII CCD area-detector diffractometer	1877 independent reflections
Radiation source: fine-focus sealed tube	1693 reflections with I > 2σ(I)
graphite	Rint = 0.044
φ–ω scan	θmax = 26.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −21→21
Tmin = 0.275, Tmax = 0.693	k = −8→8
7045 measured reflections	l = −19→19

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.064	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	w = 1/[σ2(Fo2) + (0.0343P)2 + 6.3133P] where P = (Fo2 + 2Fc2)/3
1877 reflections	(Δ/σ)max < 0.001
132 parameters	Δρmax = 1.51 e Å−3
0 restraints	Δρmin = −0.89 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	Occ. (<1)
Pt1	0.5000	0.5000	0.0000	0.01584 (10)
Cl1	0.39171 (5)	0.65021 (15)	−0.07921 (6)	0.0228 (2)
Cl2	0.50224 (6)	0.69911 (14)	0.11747 (7)	0.0226 (2)
N1	0.1742 (2)	−0.0639 (6)	−0.1087 (3)	0.0250 (8)
H1	0.139 (3)	−0.108 (7)	−0.096 (3)	0.030*
C2	0.2331 (3)	−0.0133 (5)	−0.0434 (3)	0.0193 (9)
H2	0.2297	−0.0254	0.0163	0.023*
C3	0.3001 (2)	0.0577 (6)	−0.0639 (2)	0.0160 (8)
C4	0.3007 (2)	0.0717 (7)	−0.1528 (3)	0.0223 (8)
H4	0.3455	0.1183	−0.1690	0.027*
C5	0.2379 (3)	0.0195 (6)	−0.2176 (3)	0.0305 (12)
H5	0.2391	0.0310	−0.2781	0.037*
C6	0.1730 (3)	−0.0497 (7)	−0.1941 (3)	0.0304 (10)
H6	0.1288	−0.0861	−0.2378	0.036*
N7	0.36384 (19)	0.1145 (5)	−0.0011 (2)	0.0176 (7)
C8	0.3757 (2)	0.0918 (6)	0.0896 (3)	0.0214 (9)
O9	0.3290 (2)	0.0132 (4)	0.1240 (3)	0.0367 (10)
N10	0.4417 (2)	0.1661 (6)	0.1358 (2)	0.0275 (9)
C11A	0.4643 (5)	0.2153 (13)	0.2283 (5)	0.0202 (16)*	0.50
H11A	0.4227	0.1819	0.2582	0.024*	0.50
H11B	0.4740	0.3528	0.2351	0.024*	0.50
C11B	0.4631 (5)	0.1063 (12)	0.2315 (5)	0.0185 (16)*	0.50
H11C	0.4728	−0.0314	0.2365	0.022*	0.50
H11D	0.4213	0.1381	0.2614	0.022*	0.50
H7	0.400 (3)	0.164 (6)	−0.020 (3)	0.022*
H10	0.467 (3)	0.219 (7)	0.116 (3)	0.032*

	U11	U22	U33	U12	U13	U23
Pt1	0.01344 (14)	0.01733 (15)	0.01748 (14)	−0.00161 (7)	0.00507 (9)	−0.00225 (7)
Cl1	0.0172 (5)	0.0302 (5)	0.0211 (5)	0.0044 (4)	0.0046 (4)	0.0037 (4)
Cl2	0.0192 (5)	0.0254 (5)	0.0239 (5)	−0.0025 (4)	0.0062 (4)	−0.0096 (4)
N1	0.0220 (19)	0.0246 (19)	0.030 (2)	−0.0071 (16)	0.0105 (16)	−0.0072 (17)
C2	0.019 (2)	0.019 (2)	0.021 (2)	−0.0005 (14)	0.0066 (19)	−0.0024 (15)
C3	0.020 (2)	0.0134 (17)	0.0147 (19)	0.0009 (16)	0.0045 (16)	−0.0006 (16)
C4	0.020 (2)	0.030 (2)	0.018 (2)	−0.0010 (18)	0.0067 (17)	−0.0012 (18)
C5	0.023 (3)	0.050 (3)	0.018 (2)	0.0020 (19)	0.004 (2)	−0.0089 (18)
C6	0.023 (2)	0.040 (2)	0.026 (3)	−0.002 (2)	0.003 (2)	−0.017 (2)
N7	0.0184 (17)	0.0221 (18)	0.0135 (16)	−0.0055 (13)	0.0064 (14)	0.0016 (13)
C8	0.019 (2)	0.033 (2)	0.0128 (19)	0.0068 (17)	0.0043 (16)	0.0044 (17)
O9	0.028 (2)	0.063 (3)	0.0219 (18)	−0.0011 (14)	0.0108 (16)	0.0151 (14)
N10	0.022 (2)	0.046 (2)	0.0143 (18)	−0.0013 (16)	0.0037 (15)	−0.0045 (16)

Pt1—Cl1i	2.2971 (9)	C6—H6	0.9500
Pt1—Cl1	2.2971 (9)	N7—C8	1.389 (5)
Pt1—Cl2i	2.3028 (9)	N7—H7	0.83 (5)
Pt1—Cl2	2.3028 (9)	C8—O9	1.223 (5)
N1—C6	1.330 (6)	C8—N10	1.337 (6)
N1—C2	1.331 (6)	N10—C11A	1.447 (8)
N1—H1	0.76 (5)	N10—C11B	1.511 (9)
C2—C3	1.397 (6)	N10—H10	0.71 (5)
C2—H2	0.9500	C11A—C11Bii	1.513 (10)
C3—N7	1.377 (5)	C11A—H11A	0.9900
C3—C4	1.392 (5)	C11A—H11B	0.9900
C4—C5	1.374 (7)	C11B—C11Aii	1.513 (10)
C4—H4	0.9500	C11B—H11C	0.9900
C5—C6	1.380 (7)	C11B—H11D	0.9900
C5—H5	0.9500
Cl1i—Pt1—Cl1	180.0	C3—N7—C8	126.6 (3)
Cl1i—Pt1—Cl2i	90.11 (4)	C3—N7—H7	116 (3)
Cl1—Pt1—Cl2i	89.89 (4)	C8—N7—H7	117 (3)
Cl1i—Pt1—Cl2	89.89 (4)	O9—C8—N10	123.1 (4)
Cl1—Pt1—Cl2	90.11 (4)	O9—C8—N7	122.6 (4)
Cl2i—Pt1—Cl2	180.0	N10—C8—N7	114.3 (4)
C6—N1—C2	124.9 (4)	C8—N10—C11A	129.8 (5)
C6—N1—H1	118 (4)	C8—N10—C11B	114.3 (4)
C2—N1—H1	117 (4)	C11A—N10—C11B	30.3 (4)
N1—C2—C3	119.0 (4)	C8—N10—H10	122 (4)
N1—C2—H2	120.5	C11A—N10—H10	105 (4)
C3—C2—H2	120.5	C11B—N10—H10	123 (4)
N7—C3—C4	119.4 (4)	N10—C11A—C11Bii	107.6 (6)
N7—C3—C2	123.4 (4)	N10—C11A—H11A	110.2
C4—C3—C2	117.2 (4)	C11Bii—C11A—H11A	110.2
C5—C4—C3	121.3 (4)	N10—C11A—H11B	110.2
C5—C4—H4	119.3	C11Bii—C11A—H11B	110.2
C3—C4—H4	119.3	H11A—C11A—H11B	108.5
C4—C5—C6	119.4 (5)	N10—C11B—C11Aii	105.2 (5)
C4—C5—H5	120.3	N10—C11B—H11C	110.7
C6—C5—H5	120.3	C11Aii—C11B—H11C	110.7
N1—C6—C5	118.1 (4)	N10—C11B—H11D	110.7
N1—C6—H6	121.0	C11Aii—C11B—H11D	110.7
C5—C6—H6	121.0	H11C—C11B—H11D	108.8
C6—N1—C2—C3	−1.1 (7)	C3—N7—C8—O9	1.0 (7)
N1—C2—C3—N7	179.7 (4)	C3—N7—C8—N10	−177.7 (4)
N1—C2—C3—C4	0.2 (6)	O9—C8—N10—C11A	−17.3 (8)
N7—C3—C4—C5	−178.9 (4)	N7—C8—N10—C11A	161.5 (6)
C2—C3—C4—C5	0.6 (6)	O9—C8—N10—C11B	13.7 (7)
C3—C4—C5—C6	−0.5 (7)	N7—C8—N10—C11B	−167.5 (5)
C2—N1—C6—C5	1.2 (7)	C8—N10—C11A—C11Bii	122.2 (6)
C4—C5—C6—N1	−0.3 (7)	C11B—N10—C11A—C11Bii	53.4 (10)
C4—C3—N7—C8	−172.8 (4)	C8—N10—C11B—C11Aii	−176.5 (5)
C2—C3—N7—C8	7.7 (6)	C11A—N10—C11B—C11Aii	−48.3 (10)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl2iii	0.76 (5)	2.55 (5)	3.259 (4)	156 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯Cl2i	0.76 (5)	2.55 (5)	3.259 (4)	156 (5)

Symmetry code: (i) .