4,4′-(Ethene-1,2-di­yl)dipyridinium 4-[2-(pyridin-4-yl)ethen­yl]pyridinium octa­cyanidomolybdate(V) tetra­hydrate

Yang, X.-Z.; Hu, A.-Y.; Yuan, A.-H.

doi:10.1107/S1600536813002985

metal-organic compounds

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4,4′-(Ethene-1,2-diyl)dipyridinium 4-[2-(pyridin-4-yl)ethenyl]pyridinium octacyanidomolybdate(V) tetrahydrate

Xiao-Zhen Yang,^a Ai-Yun Hu ^b and Ai-Hua Yuan ^b ^*

^aSchool of Material Science and Engineering, Jiangsu University of Science and Technology, Zhenjiang 212003, People's Republic of China, and ^bSchool of Biology and Chemical Engineering, Jiangsu University of Science and Technology, Zhenjiang 212003, People's Republic of China
^*Correspondence e-mail: aihuayuan@163.com

(Received 24 January 2013; accepted 29 January 2013; online 2 February 2013)

The crystal structure of the title compound, (C₁₂H₁₂N₂)(C₁₂H₁₁N₂)[Mo(CN)₈]·4H₂O, consists of 4,4′-(ethene-1,2-diyl)dipyridinium and 4-[2-(pyridin-4-yl)ethenyl]pyridinium cations disordered over the same site, an [Mo(CN)₈]³⁻ anion and four water molecules of crystallization. The eight-coordinate [Mo(CN)₈]³⁻ unit exhibits a slightly distorted square-antiprismatic geometry. In the structure, the cations (crystallographic symmetry, 2) and anions (crystallographic symmetry, 222) are arranged alternately by N—H⋯O and O—H⋯N hydrogen bonds, forming layers parallel to the bc plane. These layers are further linked through O—H⋯N hydrogen bonds, generating a three-dimensional supramolecular network.

Related literature

For general background to the design and construction of multi-functional materials, see: Nowicka et al. (2012 ); Prins et al. (2007 ); Sieklucka et al. (2011 ); Tanase et al. (2008 ); Zhou et al. (2012 ). For related structures, see: Liu et al. (2008 ); Qian et al. (2009 ).

Experimental

Crystal data

(C₁₂H₁₂N₂)(C₁₂H₁₁N₂)[Mo(CN)₈]·4H₂O
M_r = 743.63
Orthorhombic, C c c a
a = 12.403 (3) Å
b = 16.534 (3) Å
c = 15.370 (3) Å
V = 3151.8 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.48 mm⁻¹
T = 291 K
0.18 × 0.15 × 0.13 mm

Data collection

Bruker SMART APEXII diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.919, T_max = 0.941
6789 measured reflections
1442 independent reflections
1388 reflections with I > 2σ(I)
R_int = 0.016

Refinement

R[F² > 2σ(F²)] = 0.021
wR(F²) = 0.052
S = 1.09
1442 reflections
112 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N1ⁱ	0.85	2.11	2.9524 (19)	174
O1—H1B⋯N2ⁱⁱ	0.85	2.00	2.8195 (18)	162
N3—H3X⋯O1	0.89	1.86	2.7342 (17)	166
Symmetry codes: (i) $[x+1, y-{\script{1\over 2}}, -z]$ ; (ii) $[-x+{\script{1\over 2}}, -y, z]$ .

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813002985/rz5039sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813002985/rz5039Isup2.hkl

checkCIF report

Comment top

In the past few years, much attention has been put into the design and construction of multi-functional materials (Zhou et al., 2012). Octacyanometallates [M(CN)₈]ⁿ^- (M = Mo, W; n = 3, 4) with flexible coordination modes and lower symmetries have been aggressively studied recently (Nowicka et al., 2012), because these building blocks can adopt various geometries, e.g., square antiprismatic, dodecahedral or bicapped trigonal prismatic, depending on the external environments. The combination of the [M(CN)₈]ⁿ^- precusors and the second metal centers has produced various dimensional molecular structures and the resulting materials have displayed intriguing properties (Sieklucka et al., 2011). However, the development of octacyano- and lanthanide-based assemblies has been somewhat hampered by the tendency of the lanthanide ions to adopt higher coordination numbers, their ability to easily adapt to a given environment, and in the absence of design strategies for 4f-4d/5d networks. Recently, we used [Mo^V(CN)₈]^3- as building block to react with the lanthanide ion Ce³⁺ and dpe ligand (dpe = 1,2-di(pyridin-4-yl)ethylene), in order to obtain new octacyanide-based 4f/4 d compound with open structure. Unfortunately, a new ion-pair compound without Ce³⁺ ions was isolated. The asymmetric unit of the title compound contains 4,4'-ethene-1,2-diyldipyridinium, [H₂dpe]²⁺, and 4-(2-(pyridin-4-yl)ethenyl)pyridinium, [Hdpe]⁺, cations, one [Mo(CN)₈]^3- anion, and four crystallized water molecules (Fig. 1). Both the [H₂dpe]²⁺ and [Hdpe]⁺ cations are disordered over the same site. The eight-coordinated [Mo(CN)₈] unit exhibits a distorted slightly square antiprismatic geometry, typical of octacyanometalates (Prins et al., 2007; Tanase et al., 2008). The average distances of Mo1—C and C—N bonds are 2.1682 and 1.156 Å, respectively, while the Mo1—CN bonds are almost linear with the maximum deviation from linearity of 3.8°.

In the structure, [H₂dpe]²⁺ cation, [Hdpe]⁺ cation and [Mo(CN)₈]^3- unit are arranged alternatively through N3—H3X···O1 and O1—H1B···N2^v (symmetric code: (v) -x + 1/2, -y, z) hydrogen bonds (Table 1) to generate a two-dimensional layer. These layers are further interlinked through O1—H1A···N1^iv (symmetric code: (iv) x + 1, y - 1/2, -z) hydrogen bonds, forming a three-dimensional supramolecular network (Fig. 2). This structural feature has also been observed in related octacyanide-based compounds (C₁₀H₁₀N₄)(C₁₀H₉N₄)[M(CN)₈].nH₂O (M = Mo, W) (Qian et al., 2009; Liu et al., 2008).

Related literature top

For general background to the design and construction of multi-functional materials, see: Nowicka et al. (2012); Prins et al. (2007); Sieklucka et al. (2011); Tanase et al. (2008); Zhou et al. (2012). For related structures, see: Liu et al. (2008); Qian et al. (2009).

Experimental top

Single crystals of the title compound were prepared at room temperature by slow diffusion of a CH₃CN/H₂O (1:1 v/v) solution containing both Ce^III(NO₃)₃.6H₂O (0.05 mmol) and dpe (0.15 mmol) in a CH₃CN/H₂O (1:1 v/v) solution of [HN(n-C₄H₉)₃]₃[Mo^V(CN)₈].4H₂O (0.05 mmol). After four weeks, dark-blue rod-like crystals were obtained.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with thermal ellipsoids at the 30% probability level. All H atoms were removed for clarity. Symmetry codes: (i) x, -y + 1/2, -z + 1/2; (ii) -x, -y + 1/2, z; (iii) -x, y, -z + 1/2
	Fig. 2. The three-dimensional supramolecular network of the title compound.

4,4'-(Ethene-1,2-diyl)dipyridinium 4-[2-(pyridin-4-yl)ethenyl]pyridinium octacyanidomolybdate(V) tetrahydrate top

Crystal data top

(C₁₂H₁₂N₂)(C₁₂H₁₁N₂)[Mo(CN)₈]·4H₂O	F(000) = 1524
M_r = 743.63	D_x = 1.567 Mg m⁻³
Orthorhombic, Ccca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2b 2bc	Cell parameters from 6602 reflections
a = 12.403 (3) Å	θ = 3.4–29.0°
b = 16.534 (3) Å	µ = 0.48 mm⁻¹
c = 15.370 (3) Å	T = 291 K
V = 3151.8 (11) Å³	Rod, dark blue
Z = 4	0.18 × 0.15 × 0.13 mm

Data collection top

Bruker SMART APEXII diffractometer	1442 independent reflections
Radiation source: fine-focus sealed tube	1388 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.016
phi and ω scans	θ_max = 25.3°, θ_min = 3.4°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −14→14
T_min = 0.919, T_max = 0.941	k = −15→19
6789 measured reflections	l = −18→16

Refinement top

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)] = 0.021	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.052	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0237P)² + 4.1639P] where P = (F_o² + 2F_c²)/3
1442 reflections	(Δ/σ)_max < 0.001
112 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

(C₁₂H₁₂N₂)(C₁₂H₁₁N₂)[Mo(CN)₈]·4H₂O	V = 3151.8 (11) Å³
M_r = 743.63	Z = 4
Orthorhombic, Ccca	Mo Kα radiation
a = 12.403 (3) Å	µ = 0.48 mm⁻¹
b = 16.534 (3) Å	T = 291 K
c = 15.370 (3) Å	0.18 × 0.15 × 0.13 mm

Data collection top

Bruker SMART APEXII diffractometer	1442 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	1388 reflections with I > 2σ(I)
T_min = 0.919, T_max = 0.941	R_int = 0.016
6789 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.021	0 restraints
wR(F²) = 0.052	H-atom parameters constrained
S = 1.09	Δρ_max = 0.28 e Å⁻³
1442 reflections	Δρ_min = −0.31 e Å⁻³
112 parameters

Special details top

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Mo1	0.0000	0.2500	0.2500	0.01026 (10)
O1	0.65008 (10)	−0.07739 (7)	−0.07004 (7)	0.0222 (3)
H1A	0.7081	−0.0819	−0.0991	0.033*
H1B	0.6515	−0.1156	−0.0330	0.033*
N1	−0.15776 (12)	0.39926 (8)	0.18061 (8)	0.0217 (3)
N2	−0.12604 (11)	0.18087 (8)	0.07447 (9)	0.0214 (3)
N3	0.61502 (11)	0.04861 (9)	0.04165 (9)	0.0222 (3)
H3X	0.6177	0.0114	−0.0001	0.027*	0.75
C1	−0.10315 (12)	0.34816 (9)	0.20714 (9)	0.0153 (3)
C2	−0.08556 (13)	0.20481 (9)	0.13705 (10)	0.0153 (3)
C3	0.61146 (13)	0.12818 (10)	0.02559 (10)	0.0226 (4)
H3	0.6063	0.1466	−0.0314	0.027*
C4	0.61534 (13)	0.18237 (10)	0.09245 (10)	0.0197 (3)
H4	0.6125	0.2375	0.0809	0.024*
C5	0.62366 (12)	0.15508 (9)	0.17825 (10)	0.0171 (3)
C6	0.62332 (13)	0.07142 (10)	0.19249 (11)	0.0212 (4)
H6	0.6258	0.0511	0.2489	0.025*
C7	0.61929 (14)	0.01956 (10)	0.12305 (11)	0.0239 (4)
H7	0.6195	−0.0360	0.1324	0.029*
C8	0.62950 (13)	0.20979 (10)	0.25268 (10)	0.0177 (3)
H8	0.6335	0.1868	0.3078	0.021*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mo1	0.01259 (15)	0.00997 (14)	0.00822 (14)	0.000	0.000	0.000
O1	0.0281 (6)	0.0209 (6)	0.0175 (6)	0.0004 (5)	0.0046 (5)	−0.0005 (5)
N1	0.0279 (8)	0.0213 (7)	0.0158 (7)	0.0060 (6)	−0.0014 (6)	−0.0007 (6)
N2	0.0263 (8)	0.0205 (7)	0.0175 (7)	−0.0032 (6)	−0.0032 (6)	−0.0003 (6)
N3	0.0209 (7)	0.0244 (8)	0.0213 (7)	0.0016 (6)	0.0000 (6)	−0.0098 (6)
C1	0.0185 (8)	0.0168 (8)	0.0107 (7)	−0.0012 (6)	0.0010 (6)	−0.0029 (6)
C2	0.0168 (8)	0.0125 (8)	0.0166 (8)	−0.0007 (6)	0.0011 (7)	0.0027 (6)
C3	0.0219 (8)	0.0295 (10)	0.0164 (8)	0.0023 (7)	0.0000 (7)	−0.0004 (7)
C4	0.0222 (8)	0.0181 (8)	0.0188 (8)	0.0018 (6)	0.0005 (7)	0.0007 (6)
C5	0.0141 (7)	0.0187 (8)	0.0186 (8)	0.0013 (6)	0.0003 (6)	−0.0010 (6)
C6	0.0253 (9)	0.0193 (8)	0.0190 (8)	0.0005 (7)	−0.0006 (7)	0.0013 (6)
C7	0.0255 (9)	0.0182 (9)	0.0281 (9)	0.0005 (7)	−0.0011 (8)	−0.0028 (7)
C8	0.0184 (8)	0.0199 (8)	0.0149 (8)	0.0019 (7)	−0.0011 (6)	0.0002 (6)

Geometric parameters (Å, º) top

Mo1—C2	2.1674 (16)	N3—C7	1.341 (2)
Mo1—C2ⁱ	2.1674 (16)	N3—H3X	0.8896
Mo1—C2ⁱⁱ	2.1674 (16)	C3—C4	1.364 (2)
Mo1—C2ⁱⁱⁱ	2.1674 (16)	C3—H3	0.9300
Mo1—C1ⁱ	2.1690 (16)	C4—C5	1.398 (2)
Mo1—C1ⁱⁱⁱ	2.1690 (16)	C4—H4	0.9300
Mo1—C1	2.1690 (16)	C5—C6	1.400 (2)
Mo1—C1ⁱⁱ	2.1690 (16)	C5—C8	1.460 (2)
O1—H1A	0.8501	C6—C7	1.370 (2)
O1—H1B	0.8505	C6—H6	0.9300
N1—C1	1.157 (2)	C7—H7	0.9300
N2—C2	1.155 (2)	C8—C8ⁱ	1.332 (3)
N3—C3	1.339 (2)	C8—H8	0.9300

C2—Mo1—C2ⁱ	121.37 (8)	C1ⁱⁱⁱ—Mo1—C1ⁱⁱ	107.72 (8)
C2—Mo1—C2ⁱⁱ	73.57 (8)	C1—Mo1—C1ⁱⁱ	144.64 (8)
C2ⁱ—Mo1—C2ⁱⁱ	139.67 (8)	H1A—O1—H1B	105.6
C2—Mo1—C2ⁱⁱⁱ	139.67 (8)	C3—N3—C7	121.66 (14)
C2ⁱ—Mo1—C2ⁱⁱⁱ	73.57 (8)	C3—N3—H3X	123.2
C2ⁱⁱ—Mo1—C2ⁱⁱⁱ	121.37 (8)	C7—N3—H3X	115.1
C2—Mo1—C1ⁱ	72.33 (5)	N1—C1—Mo1	177.01 (13)
C2ⁱ—Mo1—C1ⁱ	74.09 (6)	N2—C2—Mo1	176.36 (14)
C2ⁱⁱ—Mo1—C1ⁱ	142.18 (5)	N3—C3—C4	120.35 (15)
C2ⁱⁱⁱ—Mo1—C1ⁱ	77.74 (6)	N3—C3—H3	119.8
C2—Mo1—C1ⁱⁱⁱ	142.18 (5)	C4—C3—H3	119.8
C2ⁱ—Mo1—C1ⁱⁱⁱ	77.74 (6)	C3—C4—C5	120.08 (15)
C2ⁱⁱ—Mo1—C1ⁱⁱⁱ	72.33 (5)	C3—C4—H4	120.0
C2ⁱⁱⁱ—Mo1—C1ⁱⁱⁱ	74.09 (6)	C5—C4—H4	120.0
C1ⁱ—Mo1—C1ⁱⁱⁱ	144.64 (8)	C4—C5—C6	117.78 (14)
C2—Mo1—C1	74.09 (6)	C4—C5—C8	122.88 (14)
C2ⁱ—Mo1—C1	72.33 (5)	C6—C5—C8	119.32 (14)
C2ⁱⁱ—Mo1—C1	77.74 (6)	C7—C6—C5	119.78 (15)
C2ⁱⁱⁱ—Mo1—C1	142.18 (5)	C7—C6—H6	120.1
C1ⁱ—Mo1—C1	107.72 (8)	C5—C6—H6	120.1
C1ⁱⁱⁱ—Mo1—C1	83.12 (8)	N3—C7—C6	120.27 (15)
C2—Mo1—C1ⁱⁱ	77.74 (6)	N3—C7—H7	119.9
C2ⁱ—Mo1—C1ⁱⁱ	142.18 (5)	C6—C7—H7	119.9
C2ⁱⁱ—Mo1—C1ⁱⁱ	74.09 (6)	C8ⁱ—C8—C5	124.74 (18)
C2ⁱⁱⁱ—Mo1—C1ⁱⁱ	72.33 (5)	C8ⁱ—C8—H8	117.6
C1ⁱ—Mo1—C1ⁱⁱ	83.12 (8)	C5—C8—H8	117.6

Symmetry codes: (i) x, −y+1/2, −z+1/2; (ii) −x, −y+1/2, z; (iii) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1^iv	0.85	2.11	2.9524 (19)	174
O1—H1B···N2^v	0.85	2.00	2.8195 (18)	162
N3—H3X···O1	0.89	1.86	2.7342 (17)	166

Symmetry codes: (iv) x+1, y−1/2, −z; (v) −x+1/2, −y, z.

Experimental details

Crystal data
Chemical formula	(C₁₂H₁₂N₂)(C₁₂H₁₁N₂)[Mo(CN)₈]·4H₂O
M_r	743.63
Crystal system, space group	Orthorhombic, Ccca
Temperature (K)	291
a, b, c (Å)	12.403 (3), 16.534 (3), 15.370 (3)
V (Å³)	3151.8 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.48
Crystal size (mm)	0.18 × 0.15 × 0.13

Data collection
Diffractometer	Bruker SMART APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.919, 0.941
No. of measured, independent and observed [I > 2σ(I)] reflections	6789, 1442, 1388
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.021, 0.052, 1.09
No. of reflections	1442
No. of parameters	112
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.31

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SAINT (Bruker, 2004, SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2006), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1ⁱ	0.85	2.11	2.9524 (19)	173.9
O1—H1B···N2ⁱⁱ	0.85	2.00	2.8195 (18)	162.0
N3—H3X···O1	0.89	1.86	2.7342 (17)	165.7

Symmetry codes: (i) x+1, y−1/2, −z; (ii) −x+1/2, −y, z.

References

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

4,4′-(Ethene-1,2-di­yl)dipyridinium 4-[2-(pyridin-4-yl)ethen­yl]pyridinium octa­cyanidomolybdate(V) tetra­hydrate

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Experimental

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Refinement

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References

metal-organic compounds

4,4′-(Ethene-1,2-diyl)dipyridinium 4-[2-(pyridin-4-yl)ethenyl]pyridinium octacyanidomolybdate(V) tetrahydrate