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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 6| June 2013| Pages m300-m301
doi:10.1107/S1600536813011665

Bis{2-[2,5-bis­­(pyridin-2-yl)-1H-imidazol-4-yl]pyridinium} tetra­cyanidoplatinate(II) tetra­hydrate

Raquel Gámez-Heredia,a Rosa E. Navarro,a Herbert Höpfl,b Adriana Cruz-Enríquezc and José J. Campos-Gaxiolac*

aDepartamento de Investigación en Polimeros y Materiales, Universidad de Sonora, Rosales y Blvd. Luis Encinas S/N, Col. Centro, Edificio 3G, CP 83000, Hermosillo, Sonora, México, bCentro de Investigaciones Quimicas, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001, CP 62210, Cuernavaca, Morelos, México, and cFacultad de Ingenieria Mochis, Universidad Autónoma de Sinaloa, Fuente Poseidon y Prol. A. Flores S/N, CP 81223, C.U. Los Mochis, Sinaloa, México
*Correspondence e-mail: gaxiolajose@yahoo.com.mx

(Received 22 April 2013; accepted 29 April 2013; online 4 May 2013)

The asymmetric unit of the title hydrated complex salt, (C18H14N5)2[Pt(CN)4]·4H2O, consists of one 2-[2,5-bis­(pyridin-2-yl)-1H-imidazol-4-yl]pyridinium cation, half a tetra­cyanidoplatinate(II) dianion, which is located about a crystallographic inversion center, and two water mol­ecules of crystallization. The PtII atom has a square-planar coordination environment, with Pt—CCN distances of 1.992 (4) and 2.000 (4) Å. In the cation, there is an N—H⋯N hydrogen bond linking adjacent pyridinium and pyridine rings in positions 4 and 5. Despite this, the organic component is non-planar, as shown by the dihedral angles of 10.3 (2), 6.60 (19) and 15.66 (18)° between the planes of the central imidazole ring and the pyridine/pyridinium substituents in the 2-, 4- and 5-positions. In the crystal, cations and anions are linked via O—H⋯O, O—H⋯N and N—H⋯O hydrogen bonds, forming a three-dimensional network. Additional π–π, C—H⋯O and C—H⋯N contacts provide stabilization to the crystal lattice.

Related literature

For the structural, magnetic, optical and electrical properties of hydrogen-bonded inorganic–organic hybrid materials, see: Anastassiadou et al. (2000[Anastassiadou, M., Baziard-Mouysset, G. & &Payard, M. (2000). Synthesis, 13, 1814-1816.]); Crawford et al. (2004[Crawford, P. C., Gillon, A. L., Green, J., Orpen, A. G., Podesta, T. J. & Pritchard, S. V. (2004). CrystEngComm, 6, 419-428.]); Dechambenoit et al. (2006[Dechambenoit, P., Ferlay, S., Hosseini, M. W., Planeix, J. M. & Kyritsakas, N. (2006). New J. Chem. 30, 1403-1410.]); Du et al. (2013[Du, F., Zhang, H., Tian, C. & Du, S. (2013). Cryst. Growth Des. 13, 1736-1742.]); Lebeau & Innocenzi (2011[Lebeau, B. & Innocenzi, P. (2011). Chem. Soc. Rev. 40, 886-906.]); Maynard & Sykora (2008[Maynard, B. A. & Sykora, R. E. (2008). Acta Cryst. E64, m138-m139.]); Pardo et al. (2011[Pardo, R., Zayat, M. & Levy, D. (2011). Chem. Soc. Rev. 40, 672-687.]); Sanchez et al. (2005[Sanchez, C., Julián, B., Belleville, P. & Popall, M. (2005). J. Mater. Chem. 15, 3559-3592.]); Wang et al. (2010[Wang, M. S., Xu, G., Zhang, Z. J. & &Guo, G. C. (2010). Chem. Commun. 46, 361-376.]); Yao et al. (2010[Yao, H. B., Gao, M. R. & Yu, S. H. (2010). Nanoscale, 2, 323-334.]).

[Scheme 1]

Experimental

Crystal data

  • (C18H14N5)2[Pt(CN)4]·4H2O

  • Mr = 971.92

  • Monoclinic, C 2/c

  • a = 20.958 (5) Å

  • b = 12.048 (3) Å

  • c = 15.403 (3) Å

  • β = 95.483 (3)°

  • V = 3871.6 (14) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 3.69 mm−1

  • T = 100 K

  • 0.50 × 0.34 × 0.28 mm
Data collection

  • Bruker SMART CCD area detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.26, Tmax = 0.43

  • 17095 measured reflections

  • 3418 independent reflections

  • 2726 reflections with I > 2σ(I)

  • Rint = 0.066
Refinement

  • R[F2 > 2σ(F2)] = 0.032

  • wR(F2) = 0.078

  • S = 1.00

  • 3418 reflections

  • 286 parameters

  • 8 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 3.10 e Å−3

  • Δρmin = −2.27 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N5—H5′⋯N4 0.84 1.83 2.609 (4) 154
N1—H1′⋯O31i 0.84 1.94 2.771 (4) 169
O31—H31B⋯O32ii 0.84 2.02 2.778 (4) 151
O32—H32A⋯N6iii 0.84 2.12 2.937 (4) 164
O31—H31A⋯N3iv 0.84 2.05 2.822 (5) 152
O32—H32B⋯N7v 0.84 2.02 2.854 (5) 170
C6—H6⋯O32vi 0.95 2.68 3.564 (5) 155
C17—H17⋯O32vii 0.95 2.88 3.459 (5) 120
C18—H18⋯O32vii 0.95 2.70 3.375 (5) 129
C18—H18⋯N6viii 0.95 2.50 3.406 (5) 161
Symmetry codes: (i) x, y+1, z; (ii) [-x+1, y, -z+{\script{1\over 2}}]; (iii) [-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]; (iv) x, y-1, z; (v) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (vi) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (vii) x+1, y, z; (viii) [-x+{\script{3\over 2}}, -y+{\script{3\over 2}}, -z+1].

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2001[Bruker (2001). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813011665/su2593sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813011665/su2593Isup2.hkl

checkCIF report


Comment top

Hydrogen bond based inorganic–organic hybrid materials are receiving continuous interest because of their structural, magnetic, optical and electrical properties (Sanchez et al., 2005; Yao et al., 2010; Wang et al., 2010; Lebeau et al., 2011; Pardo et al., 2011; Du et al., 2013). An interesting approach for the preparation of such materials consists in the utilization of supramolecular synthons capable of forming O—H···O, O—H···N and N—H···O hydrogen bonds, through which organic cations and anionic metal complexes are linked to form crystalline inorganic–organic hybrid solids (Crawford et al., 2004; Dechambenoit et al., 2006; Maynard & Sykora, 2008). As a further contribution to this filed of research we report herein on the synthesis and crystal structure of the title compound.

The asymmetric unit of the title compound consists of one organic cation of the composition [(C18H14N5)]+, which is located in a general position, half of an independent [Pt(CN)4]2- anion, which is located on a crystallographic inversion center, and two water molecules of crystallization (Fig. 1). The Pt atom has a square-planar coordination environment with Pt—C(cyanido) distances ranging from 1.992 (4) to 2.000 (4) Å. Although two of the three pyridine substituents are linked by an intramolecular N5+—H5'···N4 hydrogen bond (Table 1), the organic component is essentially nonplanar, as shown by the dihedral angles of 10.3 (2), 6.60 (19) and 15.66 (18)°, respectively, formed between the central imidazole ring plane and the pyridine substituents in the 2-, 4- and 5-positions.

In the crystal, the cations and anions are linked by O—H···O, O—H···N and N—H···O hydrogen bonds forming a three-dimensional network (Table 1 and Fig. 2). Within the network, the organic cations are stacked through a series of π—π interactions involving the imidazole and pyridinium rings [Cg1···Cg1i distance = 3.359 (2) Å; Cg1···Cg2ii distance = 3.559 (2) Å; Cg3···Cg3iii distance = 4.023 (3) Å; Cg2···Cg3i distance = 3.929 (2) Å; Cg1= N1/C1/N2/C3/C2; Cg2 = N4/C9-C13 and Cg3 = N3/C4—C8; symmetry codes: (i) –x+1, -y+1, -z; (ii) –x+1, y, 1- z+1/2; (iii)-x+1/2, - y+3/2, -z]. Additionally, there are a number of C—H···O and C—H···N contacts present, thus providing additional stabilization to the crystal lattice (Table 1 and Fig. 2).

Related literature top

For the structural, magnetic, optical and electrical properties of hydrogen-bonded inorganic–organic hybrid materials, see: Anastassiadou et al. (2000); Crawford et al. (2004); Dechambenoit et al. (2006); Du et al. (2013); Lebeau & Innocenzi (2011); Maynard & Sykora (2008); Pardo et al. (2011); Sanchez et al. (2005); Wang et al. (2010); Yao et al. (2010).

Experimental top

The organic component in the title compound, 2-(2,5-di(pyridin-2-yl)-1H-imidazol-4-yl)pyridine, was synthesized according to a previously reported procedure (Anastassiadou et al., 2000). Single crystals of the platinum complex were prepared at room temperature by slow diffusion of a CH3CN/H2O (2 ml, 1:1 v/v) solution containing both Eu(NO3)3 . 6H2O (0.034 g, 0.08 mmol) and K2Pt(CN)4 (0.030 g, 0.08 mmol) into a CH2Cl2 (2 ml) solution of 2-(2,5-di(pyridin-2-yl)-1H-imidazol-4-yl)pyridine (0.024 g, 0.08 mmol). After two weeks, pale yellow crystals were obtained [Yield: 40%]. IR and TGA details are given in the archived CIF.

Refinement top

The C-bound H atoms were positioned geometrically and refined as riding atoms [aryl C—H = 0.95 Å and Uiso(H) = 1.2Ueq(C)]. The pyridinium N—H+ and water H atoms were located in difference Fourier maps. They were refined with distance restraints of 0.840 (1)Å, with Uiso(H) = 1.5Ueq(O, N). For the refinement of the water molecules a constraint has also been employed for the H—O—H bond angles (DANG = 1.35 (1) Å). In the final difference Fourier map a large residual density peak, 3.10 eÅ-3, and hole, -2.26 eÅ-3, were found near the Pt atom.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker 2001); data reduction: SAINT-Plus (Bruker 2001); 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: SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level [symmetry code: (i) -x + 1/2, -y + 3/2, -z + 1].
[Figure 2] Fig. 2. A view along the b axis of the crystal packing of the title compound, showing the O—H···O, O—H···N, N—H···O, C—H···O and C—H···N hydrogen bonded three-dimensional supramolecular network (hydrogen bonds are shown as dashed lines; see Table 1 for details).
Bis{2-[2,5-bis(pyridin-2-yl)-1H-imidazol-4-yl]pyridinium} tetracyanidoplatinate(II) tetrahydrate top
Crystal data top
(C18H14N5)2[Pt(CN)4]·4H2OF(000) = 1936
Mr = 971.92Dx = 1.667 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 9440 reflections
a = 20.958 (5) Åθ = 2.3–27.7°
b = 12.048 (3) ŵ = 3.69 mm−1
c = 15.403 (3) ÅT = 100 K
β = 95.483 (3)°Rectangular prism, yellow
V = 3871.6 (14) Å30.50 × 0.34 × 0.28 mm
Z = 4
Data collection top
Bruker SMART CCD area detector
diffractometer		3418 independent reflections
Radiation source: fine-focus sealed tube2726 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.066
phi and ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −24→24
Tmin = 0.26, Tmax = 0.43k = −14→14
17095 measured reflectionsl = −18→18
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.078H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.0497P)2]
where P = (Fo2 + 2Fc2)/3
3418 reflections(Δ/σ)max < 0.001
286 parametersΔρmax = 3.10 e Å−3
8 restraintsΔρmin = −2.27 e Å−3
Crystal data top
(C18H14N5)2[Pt(CN)4]·4H2OV = 3871.6 (14) Å3
Mr = 971.92Z = 4
Monoclinic, C2/cMo Kα radiation
a = 20.958 (5) ŵ = 3.69 mm−1
b = 12.048 (3) ÅT = 100 K
c = 15.403 (3) Å0.50 × 0.34 × 0.28 mm
β = 95.483 (3)°
Data collection top
Bruker SMART CCD area detector
diffractometer		3418 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2726 reflections with I > 2σ(I)
Tmin = 0.26, Tmax = 0.43Rint = 0.066
17095 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0328 restraints
wR(F2) = 0.078H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 3.10 e Å−3
3418 reflectionsΔρmin = −2.27 e Å−3
286 parameters
Special details top

Experimental. IR and TGA details for the title compound: IR(KBr, cm-1): 3406, 3385, 3268, 3100, 2129, 1661, 1596, 1501, 1447, 1235, 1139, 1096, 777, 703. TGA: Calcd. for 4H2O: 7.42. Found: 7.69% (298 - 385 K).

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Pt10.25000.75000.50000.01672 (10)
N10.96962 (15)1.0885 (2)0.10252 (19)0.0173 (7)
H1'0.973 (2)1.1564 (9)0.114 (3)0.026*
N20.92075 (14)0.9356 (2)0.05054 (18)0.0179 (7)
N30.87601 (18)1.2211 (3)−0.0001 (2)0.0226 (8)
N41.09913 (14)0.9336 (2)0.22311 (18)0.0171 (7)
N51.03998 (19)0.7543 (2)0.1645 (2)0.0189 (8)
H5'1.0631 (17)0.798 (3)0.196 (2)0.028*
N60.31880 (15)0.8613 (3)0.6676 (2)0.0256 (8)
N70.32877 (17)0.9085 (3)0.3882 (2)0.0320 (8)
C10.91839 (17)1.0457 (3)0.0535 (2)0.0181 (8)
C21.00799 (17)1.0022 (3)0.1331 (2)0.0168 (8)
C30.97619 (18)0.9069 (3)0.1007 (2)0.0170 (9)
C40.86797 (17)1.1094 (3)0.0042 (2)0.0188 (8)
C50.81594 (17)1.0555 (3)−0.0383 (2)0.0238 (9)
H50.81090.9777−0.03210.029*
C60.77141 (19)1.1165 (3)−0.0900 (2)0.0286 (10)
H60.73551.0812−0.12060.034*
C70.7798 (3)1.2285 (4)−0.0962 (3)0.0325 (11)
H70.75021.2718−0.13250.039*
C80.8316 (2)1.2785 (4)−0.0496 (3)0.0290 (10)
H80.83581.3568−0.05280.035*
C91.07022 (17)1.0222 (3)0.1828 (2)0.0172 (8)
C101.09906 (18)1.1263 (3)0.1866 (2)0.0201 (8)
H101.07801.18840.15880.024*
C111.15875 (19)1.1376 (3)0.2316 (2)0.0218 (9)
H111.17941.20790.23440.026*
C121.18881 (19)1.0470 (3)0.2727 (2)0.0225 (9)
H121.23011.05350.30370.027*
C131.15672 (18)0.9468 (3)0.2671 (2)0.0218 (9)
H131.17650.88420.29590.026*
C140.99006 (18)0.7888 (3)0.1090 (2)0.0155 (8)
C150.95298 (19)0.7094 (3)0.0622 (2)0.0196 (9)
H150.91770.73140.02260.023*
C160.9678 (2)0.5986 (3)0.0734 (3)0.0241 (9)
H160.94240.54390.04200.029*
C171.01988 (19)0.5669 (3)0.1306 (2)0.0230 (9)
H171.03060.49070.13860.028*
C181.05545 (19)0.6473 (3)0.1752 (2)0.0215 (9)
H181.09140.62690.21410.026*
C190.29365 (18)0.8199 (3)0.6075 (2)0.0204 (9)
C200.29937 (19)0.8513 (3)0.4291 (2)0.0220 (9)
O310.96490 (15)0.3159 (2)0.1280 (2)0.0341 (7)
H31A0.9379 (13)0.310 (4)0.0842 (14)0.051*
H32A0.1394 (19)0.481 (2)0.304 (2)0.051*
O320.12373 (15)0.4241 (2)0.27892 (18)0.0324 (7)
H31B0.9448 (15)0.334 (4)0.1704 (15)0.049*
H32B0.135 (2)0.426 (3)0.2280 (11)0.049*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pt10.01960 (15)0.01288 (15)0.01807 (14)0.00058 (8)0.00385 (8)−0.00070 (7)
N10.0203 (18)0.0123 (16)0.0202 (16)0.0003 (15)0.0066 (13)−0.0003 (14)
N20.0202 (18)0.0155 (17)0.0191 (16)−0.0003 (14)0.0083 (13)0.0013 (13)
N30.027 (2)0.0138 (16)0.029 (2)0.0015 (16)0.0114 (15)0.0038 (15)
N40.0224 (18)0.0111 (16)0.0184 (16)0.0006 (14)0.0048 (13)0.0000 (13)
N50.021 (2)0.016 (2)0.0201 (19)−0.0058 (14)0.0047 (14)−0.0014 (13)
N60.026 (2)0.0281 (19)0.0228 (18)−0.0027 (16)0.0053 (15)−0.0046 (15)
N70.035 (2)0.031 (2)0.031 (2)−0.0065 (17)0.0077 (16)0.0025 (16)
C10.019 (2)0.018 (2)0.0183 (19)0.0004 (17)0.0099 (16)0.0001 (16)
C20.022 (2)0.013 (2)0.0169 (19)0.0014 (17)0.0098 (15)0.0005 (16)
C30.020 (2)0.018 (2)0.0152 (19)−0.0019 (17)0.0090 (16)0.0016 (16)
C40.020 (2)0.018 (2)0.0200 (19)0.0058 (17)0.0117 (16)0.0013 (16)
C50.023 (2)0.024 (2)0.025 (2)−0.0002 (19)0.0073 (17)−0.0027 (17)
C60.026 (2)0.030 (2)0.030 (2)0.006 (2)0.0015 (17)−0.0021 (19)
C70.033 (3)0.034 (3)0.030 (3)0.011 (2)0.002 (2)0.006 (2)
C80.035 (3)0.021 (2)0.033 (3)0.005 (2)0.014 (2)0.008 (2)
C90.022 (2)0.016 (2)0.0156 (19)0.0004 (17)0.0100 (15)−0.0019 (15)
C100.028 (2)0.0115 (19)0.022 (2)0.0001 (18)0.0067 (16)0.0003 (16)
C110.025 (2)0.015 (2)0.026 (2)−0.0034 (18)0.0045 (17)−0.0038 (17)
C120.026 (2)0.019 (2)0.022 (2)−0.0032 (18)0.0025 (17)−0.0033 (17)
C130.028 (2)0.017 (2)0.021 (2)0.0022 (18)0.0054 (17)0.0052 (16)
C140.018 (2)0.0142 (17)0.016 (2)−0.0009 (18)0.0092 (16)0.0017 (16)
C150.021 (2)0.0181 (19)0.020 (2)0.0000 (19)0.0057 (16)0.0009 (17)
C160.029 (2)0.019 (2)0.025 (2)−0.0070 (19)0.0061 (18)−0.0042 (17)
C170.028 (2)0.012 (2)0.030 (2)−0.0029 (19)0.0095 (18)0.0008 (17)
C180.025 (2)0.018 (2)0.023 (2)−0.0006 (18)0.0058 (16)0.0064 (17)
C190.024 (2)0.019 (2)0.020 (2)0.0026 (18)0.0069 (17)0.0014 (17)
C200.025 (2)0.019 (2)0.022 (2)−0.0011 (18)0.0024 (17)−0.0068 (17)
O310.0371 (19)0.0219 (17)0.0444 (19)−0.0019 (15)0.0096 (14)−0.0049 (15)
O320.046 (2)0.0254 (16)0.0277 (16)−0.0057 (15)0.0115 (14)−0.0006 (13)
Geometric parameters (Å, º) top
Pt1—C201.992 (4)C6—C71.365 (5)
Pt1—C20i1.992 (4)C6—H60.9500
Pt1—C192.000 (4)C7—C81.381 (7)
Pt1—C19i2.000 (4)C7—H70.9500
N1—C11.354 (5)C8—H80.9500
N1—C21.370 (5)C9—C101.391 (5)
N1—H1'0.8400 (11)C10—C111.378 (5)
N2—C11.328 (4)C10—H100.9500
N2—C31.377 (5)C11—C121.383 (5)
N3—C81.338 (6)C11—H110.9500
N3—C41.358 (5)C12—C131.381 (5)
N4—C131.336 (5)C12—H120.9500
N4—C91.349 (4)C13—H130.9500
N5—C181.336 (4)C14—C151.391 (6)
N5—C141.351 (6)C15—C161.377 (6)
N5—H5'0.8400 (11)C15—H150.9500
N6—C191.135 (5)C16—C171.390 (6)
N7—C201.151 (4)C16—H160.9500
C1—C41.459 (5)C17—C181.367 (5)
C2—C31.396 (5)C17—H170.9500
C2—C91.467 (5)C18—H180.9500
C3—C141.455 (5)O31—H31A0.8401 (11)
C4—C51.380 (5)O31—H31B0.8400 (11)
C5—C61.379 (5)O32—H32A0.8401 (11)
C5—H50.9500O32—H32B0.8400 (11)
C20—Pt1—C20i180.00 (17)N3—C8—H8118.6
C20—Pt1—C1988.59 (15)C7—C8—H8118.6
C20i—Pt1—C1991.41 (14)N4—C9—C10121.3 (3)
C20—Pt1—C19i91.41 (14)N4—C9—C2116.6 (3)
C20i—Pt1—C19i88.59 (15)C10—C9—C2122.1 (3)
C19—Pt1—C19i180.000 (1)C11—C10—C9118.7 (3)
C1—N1—C2108.2 (3)C11—C10—H10120.6
C1—N1—H1'123 (3)C9—C10—H10120.6
C2—N1—H1'129 (3)C10—C11—C12120.3 (4)
C1—N2—C3105.3 (3)C10—C11—H11119.8
C8—N3—C4117.2 (4)C12—C11—H11119.8
C13—N4—C9118.9 (3)C13—C12—C11117.6 (4)
C18—N5—C14122.6 (4)C13—C12—H12121.2
C18—N5—H5'115 (3)C11—C12—H12121.2
C14—N5—H5'123 (3)N4—C13—C12123.1 (3)
N2—C1—N1111.6 (3)N4—C13—H13118.4
N2—C1—C4122.3 (3)C12—C13—H13118.4
N1—C1—C4125.9 (3)N5—C14—C15118.5 (4)
N1—C2—C3104.9 (3)N5—C14—C3119.5 (4)
N1—C2—C9121.2 (3)C15—C14—C3122.0 (4)
C3—C2—C9133.8 (3)C16—C15—C14119.6 (4)
N2—C3—C2110.0 (3)C16—C15—H15120.2
N2—C3—C14116.5 (3)C14—C15—H15120.2
C2—C3—C14133.5 (4)C15—C16—C17120.0 (4)
N3—C4—C5122.6 (4)C15—C16—H16120.0
N3—C4—C1117.4 (3)C17—C16—H16120.0
C5—C4—C1120.0 (3)C18—C17—C16118.8 (4)
C6—C5—C4118.9 (4)C18—C17—H17120.6
C6—C5—H5120.5C16—C17—H17120.6
C4—C5—H5120.5N5—C18—C17120.5 (4)
C7—C6—C5118.8 (4)N5—C18—H18119.7
C7—C6—H6120.6C17—C18—H18119.7
C5—C6—H6120.6N6—C19—Pt1178.6 (3)
C6—C7—C8119.6 (5)N7—C20—Pt1178.8 (3)
C6—C7—H7120.2H31A—O31—H31B107.2 (12)
C8—C7—H7120.2H32A—O32—H32B106.3 (12)
N3—C8—C7122.7 (4)
C3—N2—C1—N10.4 (4)C13—N4—C9—C10−0.4 (5)
C3—N2—C1—C4176.7 (3)C13—N4—C9—C2178.1 (3)
C2—N1—C1—N20.4 (4)N1—C2—C9—N4168.6 (3)
C2—N1—C1—C4−175.8 (3)C3—C2—C9—N4−17.0 (5)
C1—N1—C2—C3−0.9 (4)N1—C2—C9—C10−12.9 (5)
C1—N1—C2—C9175.0 (3)C3—C2—C9—C10161.5 (4)
C1—N2—C3—C2−1.0 (4)N4—C9—C10—C111.1 (5)
C1—N2—C3—C14179.5 (3)C2—C9—C10—C11−177.4 (3)
N1—C2—C3—N21.2 (4)C9—C10—C11—C12−0.7 (5)
C9—C2—C3—N2−173.9 (3)C10—C11—C12—C13−0.3 (5)
N1—C2—C3—C14−179.4 (4)C9—N4—C13—C12−0.7 (5)
C9—C2—C3—C145.5 (7)C11—C12—C13—N41.0 (5)
C8—N3—C4—C5−1.4 (5)C18—N5—C14—C150.8 (6)
C8—N3—C4—C1176.1 (3)C18—N5—C14—C3−179.9 (3)
N2—C1—C4—N3−168.9 (3)N2—C3—C14—N5−173.1 (3)
N1—C1—C4—N36.9 (5)C2—C3—C14—N57.4 (6)
N2—C1—C4—C58.7 (5)N2—C3—C14—C156.1 (5)
N1—C1—C4—C5−175.5 (3)C2—C3—C14—C15−173.3 (4)
N3—C4—C5—C62.5 (5)N5—C14—C15—C160.1 (5)
C1—C4—C5—C6−175.0 (3)C3—C14—C15—C16−179.1 (4)
C4—C5—C6—C7−1.0 (6)C14—C15—C16—C17−0.7 (5)
C5—C6—C7—C8−1.4 (7)C15—C16—C17—C180.3 (6)
C4—N3—C8—C7−1.1 (6)C14—N5—C18—C17−1.2 (6)
C6—C7—C8—N32.6 (7)C16—C17—C18—N50.6 (6)
Symmetry code: (i) −x+1/2, −y+3/2, −z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5′···N40.841.832.609 (4)154
N1—H1′···O31ii0.841.942.771 (4)169
O31—H31B···O32iii0.842.022.778 (4)151
O32—H32A···N6i0.842.122.937 (4)164
O31—H31A···N3iv0.842.052.822 (5)152
O32—H32B···N7v0.842.022.854 (5)170
C6—H6···O32vi0.952.683.564 (5)155
C17—H17···O32vii0.952.883.459 (5)120
C18—H18···O32vii0.952.703.375 (5)129
C18—H18···N6viii0.952.503.406 (5)161
Symmetry codes: (i) −x+1/2, −y+3/2, −z+1; (ii) x, y+1, z; (iii) −x+1, y, −z+1/2; (iv) x, y−1, z; (v) −x+1/2, y−1/2, −z+1/2; (vi) x+1/2, −y+3/2, z−1/2; (vii) x+1, y, z; (viii) −x+3/2, −y+3/2, −z+1.

Experimental details

Crystal data
Chemical formula(C18H14N5)2[Pt(CN)4]·4H2O
Mr971.92
Crystal system, space groupMonoclinic, C2/c
Temperature (K)100
a, b, c (Å)20.958 (5), 12.048 (3), 15.403 (3)
β (°) 95.483 (3)
V (Å3)3871.6 (14)
Z4
Radiation typeMo Kα
µ (mm−1)3.69
Crystal size (mm)0.50 × 0.34 × 0.28
Data collection
DiffractometerBruker SMART CCD area detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.26, 0.43
No. of measured, independent and
observed [I > 2σ(I)] reflections		17095, 3418, 2726
Rint0.066
(sin θ/λ)max (Å−1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.078, 1.00
No. of reflections3418
No. of parameters286
No. of restraints8
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)3.10, −2.27

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008), SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5'···N40.841.832.609 (4)154
N1—H1'···O31i0.841.942.771 (4)169
O31—H31B···O32ii0.842.022.778 (4)151
O32—H32A···N6iii0.842.122.937 (4)164
O31—H31A···N3iv0.842.052.822 (5)152
O32—H32B···N7v0.842.022.854 (5)170
C6—H6···O32vi0.952.683.564 (5)155
C17—H17···O32vii0.952.883.459 (5)120
C18—H18···O32vii0.952.703.375 (5)129
C18—H18···N6viii0.952.503.406 (5)161
Symmetry codes: (i) x, y+1, z; (ii) −x+1, y, −z+1/2; (iii) −x+1/2, −y+3/2, −z+1; (iv) x, y−1, z; (v) −x+1/2, y−1/2, −z+1/2; (vi) x+1/2, −y+3/2, z−1/2; (vii) x+1, y, z; (viii) −x+3/2, −y+3/2, −z+1.
 

Acknowledgements

This work was supported financially by the Universidad Autónoma de Sinaloa (PROFAPI 2012/032). RGH thanks the Consejo Nacional de Ciencia y Tecnologia (CONACYT) for support in the form of a scholarship.

References

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Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 69| Part 6| June 2013| Pages m300-m301
doi:10.1107/S1600536813011665
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