Literature DB >> 23476502

(1RS,2RS)-4,4'-(1-Aza-niumyl-2-hy-droxy-ethane-1,2-di-yl)dipyridinium tetra-chlorido-platinate(II) chloride.

José J Campos-Gaxiola1, Jorge L Almaral-Sanchez, Adriana Cruz-Enríquez, Herbert Höpfl, Miguel Parra-Hake.   

Abstract

The title compound, (C12H16N3O)[PtCl4]Cl, consists of a 4,4'-(1-aza-niumyl-2-hy-droxy-ethane-1,2-di-yl)dipyridinium trication, a square-planar tetra-chloridoplatinate(II) dianion and a chloride ion. In the cation, the pyridinium rings attached to the central 1-aza-niumyl-2-hy-droxy-ethane fragment have an anti conformation, as indicated by the central C-C-C-C torsion angle of -166.5 (6)°, and they are inclined to one another by 63.5 (4)°. In the crystal, the cations and anions are linked through N-H⋯Cl and O-H⋯Cl hydrogen bonds. There are also π-π contacts [centroid-centroid distances = 3.671 (4) and 3.851 (4) Å] and a number of C-H⋯Cl inter-actions present, consolidating the formation of a three-dimensional supra-molecular structure.

Entities:  

Year:  2013        PMID： 23476502      PMCID： PMC3588516          DOI： 10.1107/S160053681300425X

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For potential applications of organic-inorganic hybrid materials with magnetic, optical and electrical properties, see: Yao et al. (2010 ▶); Sanchez et al. (2011 ▶); Pardo et al. (2011 ▶); Piecha et al. (2012 ▶). For related tetra­chloro­platinate(II) compounds, see: Fusi et al. (2012 ▶); Adarsh et al. (2010 ▶); Campos-Gaxiola et al. (2010 ▶); Adams et al. (2005 ▶). For the synthesis of the title ligand, see: Campos-Gaxiola et al. (2012 ▶).

Experimental

Crystal data

(C12H16N3O)[n class="Chemical">PtCl4]Cl M = 590.62 Triclinic, a = 7.636 (2) Å b = 8.082 (2) Å c = 14.599 (4) Å α = 88.689 (4)° β = 84.240 (4)° γ = 70.148 (4)° V = 843.1 (4) Å3 Z = 2 Mo Kα radiation μ = 9.12 mm−1 T = 100 K 0.50 × 0.26 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.092, T max = 0.408 5093 measured reflections 2911 independent reflections 2726 reflections with I > 2σ(I) R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.038 wR(F 2) = 0.091 S = 1.05 2911 reflections 217 parameters 6 restraints H atoms treated by a mixture of independent and constrained refinement Δρmax = 2.34 e Å−3 Δρmin = −1.98 e Å−3 Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT-Plus-n class="Chemical">NT (Bruker 2001 ▶); data reduction: SAINT-Plus-NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶). Click here for additional data file. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681300425X/su2560sup1.cif Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681300425X/su2560Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
(C12H16N3O)[PtCl4]ClZ = 2
Mr = 590.62F(000) = 560
Triclinic, P1Dx = 2.326 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.636 (2) ÅCell parameters from 926 reflections
b = 8.082 (2) Åθ = 2.7–27.5°
c = 14.599 (4) ŵ = 9.12 mm−1
α = 88.689 (4)°T = 100 K
β = 84.240 (4)°Rectangular prism, orange
γ = 70.148 (4)°0.50 × 0.26 × 0.12 mm
V = 843.1 (4) Å3
Bruker SMART CCD area-detector diffractometer2911 independent reflections
Radiation source: fine-focus sealed tube2726 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
phi and ω scansθmax = 25.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −8→9
Tmin = 0.092, Tmax = 0.408k = −8→9
5093 measured reflectionsl = −17→16
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091H atoms treated by a mixture of independent and constrained refinement
S = 1.05w = 1/[σ2(Fo2) + (0.043P)2] where P = (Fo2 + 2Fc2)/3
2911 reflections(Δ/σ)max < 0.001
217 parametersΔρmax = 2.34 e Å−3
6 restraintsΔρmin = −1.98 e Å−3
Experimental. Spectroscopic and other analytical data for the title compound: IR (KBr, cm-1): 3409, 3198, 3071, 2882, 2825, 1706, 1620, 1500, 1417, 1331, 1295, 1232, 1031, 857 and 693. TGA: Calcd. for HCl: 4.32. Found: 4.75% (310–398 K); Calcd. for 2HCl: 8.65. Found: 8.23% (398–498 K).
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles
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.
xyzUiso*/Ueq
O1−0.0077 (7)0.6320 (7)0.1932 (4)0.0269 (17)
N10.3686 (8)0.5578 (8)0.1506 (4)0.0204 (17)
N20.0968 (8)1.1792 (8)0.0449 (4)0.0209 (19)
N30.2400 (9)0.3227 (9)0.4748 (4)0.025 (2)
C10.2559 (9)0.7175 (9)0.2054 (5)0.018 (2)
C20.0855 (10)0.6886 (9)0.2597 (5)0.021 (2)
C30.1431 (9)0.5553 (9)0.3366 (5)0.019 (2)
C40.2175 (10)0.5946 (10)0.4125 (5)0.023 (2)
C50.2658 (10)0.4784 (10)0.4820 (5)0.024 (2)
C60.1694 (11)0.2782 (10)0.4047 (5)0.027 (3)
C70.1181 (10)0.3947 (9)0.3338 (5)0.022 (2)
C80.1965 (9)0.8788 (9)0.1453 (5)0.019 (2)
C90.0633 (10)1.0334 (9)0.1822 (5)0.022 (2)
C100.0133 (10)1.1822 (9)0.1300 (5)0.022 (2)
C110.2254 (10)1.0358 (9)0.0076 (5)0.022 (2)
C120.2759 (10)0.8818 (9)0.0559 (5)0.020 (2)
Pt10.63165 (3)0.09264 (3)0.31275 (2)0.0146 (1)
Cl10.6085 (3)−0.1851 (2)0.32558 (12)0.0222 (6)
Cl20.4705 (3)0.1426 (2)0.18394 (12)0.0226 (5)
Cl30.6558 (2)0.3685 (2)0.30103 (12)0.0192 (5)
Cl40.8053 (3)0.0399 (2)0.43690 (13)0.0259 (6)
Cl50.2607 (2)0.4569 (2)0.96236 (11)0.0201 (5)
H10.334500.737900.249900.0210*
H1'−0.117 (5)0.650 (12)0.218 (5)0.0400*
H1A0.317 (10)0.528 (10)0.107 (4)0.0310*
H1B0.480 (4)0.560 (11)0.137 (5)0.0310*
H1C0.407 (11)0.467 (6)0.185 (4)0.0310*
H20.002000.801000.286800.0250*
H2'0.071 (11)1.280 (4)0.022 (5)0.0320*
H3'0.273 (11)0.258 (9)0.520 (4)0.0370*
H40.234800.702700.416000.0270*
H50.315200.505500.532900.0290*
H60.154200.169000.403000.0320*
H70.066700.364900.284200.0270*
H90.008401.035500.242200.0260*
H10−0.078101.284700.153800.0270*
H110.281601.03940−0.051600.0270*
H120.363100.780100.028900.0240*
U11U22U33U12U13U23
O10.026 (3)0.035 (3)0.023 (3)−0.015 (3)−0.001 (2)−0.001 (2)
N10.020 (3)0.021 (3)0.018 (3)−0.005 (3)0.001 (3)0.002 (3)
N20.022 (3)0.013 (3)0.027 (4)−0.006 (3)0.000 (3)0.002 (3)
N30.020 (3)0.029 (4)0.020 (4)−0.003 (3)0.004 (3)0.005 (3)
C10.015 (3)0.019 (4)0.018 (4)−0.005 (3)−0.002 (3)0.000 (3)
C20.021 (4)0.021 (4)0.019 (4)−0.004 (3)−0.002 (3)0.000 (3)
C30.018 (4)0.024 (4)0.011 (3)−0.006 (3)0.006 (3)0.000 (3)
C40.027 (4)0.022 (4)0.019 (4)−0.010 (3)0.005 (3)−0.007 (3)
C50.025 (4)0.032 (4)0.016 (4)−0.012 (3)0.001 (3)−0.006 (3)
C60.036 (5)0.023 (4)0.023 (4)−0.016 (4)0.008 (3)−0.003 (3)
C70.029 (4)0.026 (4)0.014 (4)−0.012 (3)−0.002 (3)−0.004 (3)
C80.020 (4)0.022 (4)0.017 (4)−0.011 (3)0.001 (3)−0.005 (3)
C90.026 (4)0.020 (4)0.020 (4)−0.010 (3)0.004 (3)0.000 (3)
C100.030 (4)0.018 (4)0.017 (4)−0.007 (3)0.004 (3)−0.003 (3)
C110.032 (4)0.022 (4)0.016 (4)−0.013 (3)−0.002 (3)0.002 (3)
C120.021 (4)0.020 (4)0.018 (4)−0.007 (3)0.003 (3)−0.003 (3)
Pt10.0164 (2)0.0135 (2)0.0136 (2)−0.0049 (1)−0.0005 (1)−0.0017 (1)
Cl10.0271 (10)0.0188 (9)0.0244 (10)−0.0119 (8)−0.0050 (7)0.0010 (7)
Cl20.0248 (10)0.0238 (9)0.0193 (9)−0.0077 (8)−0.0047 (7)−0.0010 (7)
Cl30.0255 (9)0.0136 (8)0.0182 (9)−0.0068 (7)0.0000 (7)−0.0018 (6)
Cl40.0365 (11)0.0214 (9)0.0243 (10)−0.0127 (8)−0.0144 (8)0.0043 (7)
Cl50.0198 (9)0.0204 (9)0.0201 (9)−0.0076 (7)0.0006 (7)0.0024 (7)
Pt1—Cl22.303 (2)C3—C41.384 (11)
Pt1—Cl32.2999 (17)C3—C71.377 (10)
Pt1—Cl12.3127 (18)C4—C51.358 (11)
Pt1—Cl42.300 (2)C6—C71.378 (10)
O1—C21.428 (10)C8—C121.386 (10)
O1—H1'0.84 (6)C8—C91.394 (10)
N1—C11.484 (9)C9—C101.370 (10)
N2—C111.324 (9)C11—C121.372 (10)
N2—C101.335 (9)C1—H10.9800
N3—C61.314 (10)C2—H20.9800
N3—C51.346 (10)C4—H40.9300
N1—H1B0.86 (5)C5—H50.9300
N1—H1C0.86 (5)C6—H60.9300
N1—H1A0.86 (7)C7—H70.9300
N2—H2'0.84 (4)C9—H90.9300
N3—H3'0.84 (6)C10—H100.9300
C1—C21.539 (11)C11—H110.9300
C1—C81.517 (10)C12—H120.9300
C2—C31.529 (10)
Cl3—Pt1—Cl489.28 (6)C3—C7—C6119.8 (7)
Cl1—Pt1—Cl490.27 (7)C9—C8—C12118.2 (6)
Cl1—Pt1—Cl290.20 (6)C1—C8—C9119.2 (6)
Cl1—Pt1—Cl3179.55 (7)C1—C8—C12122.6 (6)
Cl2—Pt1—Cl390.24 (6)C8—C9—C10119.9 (7)
Cl2—Pt1—Cl4177.33 (8)N2—C10—C9119.6 (7)
C2—O1—H1'105 (5)N2—C11—C12120.3 (7)
C10—N2—C11122.4 (6)C8—C12—C11119.6 (7)
C5—N3—C6123.5 (7)C8—C1—H1108.00
C1—N1—H1C112 (4)N1—C1—H1108.00
H1A—N1—H1B117 (7)C2—C1—H1108.00
C1—N1—H1A117 (5)C3—C2—H2109.00
H1B—N1—H1C93 (8)O1—C2—H2109.00
C1—N1—H1B109 (5)C1—C2—H2109.00
H1A—N1—H1C107 (7)C3—C4—H4119.00
C11—N2—H2'125 (5)C5—C4—H4119.00
C10—N2—H2'112 (5)N3—C5—H5121.00
C6—N3—H3'124 (5)C4—C5—H5121.00
C5—N3—H3'113 (5)C7—C6—H6120.00
N1—C1—C8111.6 (6)N3—C6—H6120.00
N1—C1—C2110.4 (6)C3—C7—H7120.00
C2—C1—C8111.2 (6)C6—C7—H7120.00
O1—C2—C1105.6 (6)C8—C9—H9120.00
O1—C2—C3112.3 (6)C10—C9—H9120.00
C1—C2—C3111.8 (6)C9—C10—H10120.00
C2—C3—C7121.2 (7)N2—C10—H10120.00
C2—C3—C4120.9 (6)N2—C11—H11120.00
C4—C3—C7118.0 (7)C12—C11—H11120.00
C3—C4—C5121.3 (7)C11—C12—H12120.00
N3—C5—C4118.0 (7)C8—C12—H12120.00
N3—C6—C7119.5 (7)
C11—N2—C10—C91.2 (12)C1—C2—C3—C468.4 (9)
C10—N2—C11—C121.0 (12)C1—C2—C3—C7−113.4 (8)
C6—N3—C5—C4−0.6 (12)C2—C3—C4—C5178.7 (7)
C5—N3—C6—C70.1 (12)C7—C3—C4—C50.4 (12)
N1—C1—C2—O1−53.4 (7)C2—C3—C7—C6−179.2 (7)
N1—C1—C2—C369.1 (7)C4—C3—C7—C6−0.9 (11)
C8—C1—C2—O171.1 (7)C3—C4—C5—N30.3 (12)
C8—C1—C2—C3−166.5 (6)N3—C6—C7—C30.7 (12)
N1—C1—C8—C9168.8 (7)C1—C8—C9—C10177.5 (7)
N1—C1—C8—C12−14.3 (10)C12—C8—C9—C100.5 (11)
C2—C1—C8—C945.1 (9)C1—C8—C12—C11−175.3 (7)
C2—C1—C8—C12−138.1 (7)C9—C8—C12—C111.6 (11)
O1—C2—C3—C4−173.2 (7)C8—C9—C10—N2−1.9 (12)
O1—C2—C3—C75.1 (10)N2—C11—C12—C8−2.4 (12)
D—H···AD—HH···AD···AD—H···A
O1—H1′···Cl1i0.84 (6)2.49 (7)3.250 (6)152 (6)
N1—H1A···Cl5ii0.86 (7)2.32 (6)3.148 (6)162 (7)
N1—H1B···Cl5iii0.86 (5)2.30 (6)3.097 (7)154 (7)
N1—H1C···Cl20.86 (5)2.50 (5)3.214 (6)141 (6)
N1—H1C···Cl30.86 (5)2.58 (7)3.242 (6)134 (6)
N2—H2′···Cl5iv0.84 (4)2.45 (7)3.088 (6)134 (7)
N2—H2′···Cl5v0.84 (4)2.69 (6)3.272 (6)128 (7)
N3—H3′···Cl1vi0.84 (6)2.50 (6)3.275 (6)155 (6)
N3—H3′···Cl4vi0.84 (6)2.72 (7)3.286 (7)127 (7)
C1—H1···Cl1vii0.982.713.660 (8)163
C5—H5···Cl3iii0.932.713.604 (8)162
C10—H10···Cl3i0.932.733.459 (8)136
C10—H10···Cl5v0.932.743.308 (7)120
C11—H11···Cl2viii0.932.643.449 (8)145
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
O1—H1′⋯Cl1i 0.84 (6)2.49 (7)3.250 (6)152 (6)
N1—H1A⋯Cl5ii 0.86 (7)2.32 (6)3.148 (6)162 (7)
N1—H1B⋯Cl5iii 0.86 (5)2.30 (6)3.097 (7)154 (7)
N1—H1C⋯Cl20.86 (5)2.50 (5)3.214 (6)141 (6)
N1—H1C⋯Cl30.86 (5)2.58 (7)3.242 (6)134 (6)
N2—H2′⋯Cl5iv 0.84 (4)2.45 (7)3.088 (6)134 (7)
N2—H2′⋯Cl5v 0.84 (4)2.69 (6)3.272 (6)128 (7)
N3—H3′⋯Cl1vi 0.84 (6)2.50 (6)3.275 (6)155 (6)
N3—H3′⋯Cl4vi 0.84 (6)2.72 (7)3.286 (7)127 (7)
C1—H1⋯Cl1vii 0.982.713.660 (8)163
C5—H5⋯Cl3iii 0.932.713.604 (8)162
C10—H10⋯Cl3i 0.932.733.459 (8)136
C10—H10⋯Cl5v 0.932.743.308 (7)120
C11—H11⋯Cl2viii 0.932.643.449 (8)145

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) ; (viii) .

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