4,4′-Diazenediyldipyridinium (4-pyridyldiazen­yl)pyridinium octa­cyanidomolyb­date(V) tetra­hydrate

Liu, W.-Y.; Zhou, H.; Yuan, A.-H.

doi:10.1107/S160053680802494X

metal-organic compounds

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Volume 64| Part 9| September 2008| Page m1151

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4,4′-Diazenediyldipyridinium (4-pyridyldiazenyl)pyridinium octacyanidomolybdate(V) tetrahydrate

Wen-Yan Liu,^a Hu Zhou ^a and Ai-Hua Yuan ^a ^*

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

(Received 23 June 2008; accepted 3 August 2008; online 13 August 2008)

The structure of the title complex, (C₁₀H₁₀N₄)(C₁₀H₉N₄)[Mo(CN)₈]·4H₂O, consists of 4,4′-diazenediyldipyridinium and (4-pyridyldiazenyl)pyridinium cations disordered over the same site, an [Mo(CN)₈]³⁻ anion and four uncoordinated water molecules. The cations (crystallographic symmetry, 2) and the [Mo(CN)₈]³⁻ anion (crystallographic symmetry, 222) are arranged in an alternating fashion, forming a two-dimensional layered structure through hydrogen bonds. Hydrogen bonds, π–π stacking interactions (shortest distance = 4.7872 Å) and van der Waals forces between adjacent layers generate a three-dimensional supramolecular structure.

Related literature

For information on octacyanidometalate-based compounds complexes, see: Chelebaeva et al. (2008 ); Ikeda et al. (2005 ); Kosaka et al. (2007 ); Matoga et al. (2005 ); Prins et al. (2007 ); Przychodzeń et al. (2007 ); Wang et al. (2006 ).

Experimental

Crystal data

(C₁₀H₁₀N₄)(C₁₀H₉N₄)[Mo(CN)₈]·4H₂O
M_r = 747.60
Orthorhombic, C c c a
a = 16.259 (5) Å
b = 12.787 (4) Å
c = 15.442 (5) Å
V = 3210.5 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.47 mm⁻¹
T = 291 (2) K
0.28 × 0.26 × 0.24 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.879, T_max = 0.895
13328 measured reflections
1851 independent reflections
1540 reflections with I > 2σ(I)
R_int = 0.050

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.065
S = 1.06
1851 reflections
121 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O1	0.86 (4)	1.86 (4)	2.675 (3)	157 (3)
O1—H1A⋯N2ⁱ	0.85 (3)	2.06 (3)	2.809 (3)	147 (3)
O1—H1B⋯N1ⁱⁱ	0.85 (3)	2.40 (3)	3.164 (3)	150 (3)
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680802494X/br2078sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680802494X/br2078Isup2.hkl

checkCIF report

Comment top

Recently, the design and synthesis of multifunctional materials with lanthanide octacyanometalate-based metal assemblies are attracting much more interest (Chelebaeva et al., 2008; Przychodzeń et al., 2007; Ikeda et al., 2005; Kosaka et al., 2007; Matoga et al., 2005; Wang et al., 2006). The combination of the octacyanometalate [M(CN)₈]^3-/4- (M = Mo,W) building blocks with the lanthanide ions plays an important part in the construction of new supramolecular magnetic materials (Prins et al., 2007). In search of a new lanthanide-containing octacyanometalate-based magnet using [Mo^V(CN)₈]^3-and Ce³⁺as the building blocks, we tired to employ 4,4'-azpy (4,4'-azobispyridine) as the primary ligand for coordination. However, the unexpected octacyanomolybdate(V)-based supramolecular complex [H₃(4,4'-azpy)₂][Mo(CN)₈].4H₂O without Ce³⁺ was obtained instead.

The title complex consists of [H₂(4,4'-azpy)]²⁺ and [H(4,4'-azpy)]⁺ cations disordered over the same site, [Mo(CN)₈]^3- anion and crystallized water molecules (Fig. 1). It is worth noting that [H₂(4,4'-azpy)]²⁺ and [H(4,4'-azpy)]⁺ cations are both disordered over the same site.

In the structure, the eight CN groups are all terminal ones and the average distance of Mo—C is 2.1582 Å. The center Mo atom is coordinated by eight cyano groups in a distorted square antiprism. [H₂(4,4'-azpy)]²⁺ cation, [H(4,4'-azpy)]⁺ cation (crystallographic symmetry, 2), and [Mo(CN)₈]^3- anion (crystallographic symmetry, 222) arranged in an alternating fashion to form a two-dimensional layered structure (Fig. 2) through O1—H1A···N2 and N3—H3A···O1 hydrogen-bonds. Then, a three-dimension supramolecular structure (Fig. 3) was formed through O1—H1B···N1 hydrogen-bonds, π-π packing and Van der Waals forces between adjacent layers.

Related literature top

For information based on octacyanometalate-based compounds complexes see: Chelebaeva et al. (2008); Ikeda et al. (2005); Kosaka et al. (2007); Matoga et al. (2005); Prins et al. (2007); Przychodzeń et al. (2007); Wang et al. (2006).

Experimental top

Single crystals of the title complex were prepared at room temperature in the dark by slow diffusion of anacetonitrile solution (2 ml) containing both Ce(NO₃)₃.6H₂O (21.71 mg, 0.05 mmol) and 4,4'-azpy (9.21 mg, 0.05 mmol) into an acetonitrile solution (20 ml) of [HN(n—C₄H₉)₃]₃[Mo(CN)₈].4H₂O (46.60 mg, 0.05 mmol). After two weeks, pale yellow crystals were obtained.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title complex showing 30% probability displacement ellipsoids. H atoms are not shown for clarity.
	Fig. 2. View in the ac plane of the hydrogen-bonding interactions in the title complex. [Symmetry codes: A: 0.5 - x, 1.5 - y, 1 - z; B: 1/2 + x, y, 1 - z; C: 1 - x,1.5 - y, z; D: 0.5 - x, -1/2 + y, 1.5 - z; E: 0.5 - x, 1 - y, z; F: x, 1.5 - y, 1.5 - z; G: 1 - x, 1 - y, 1 - z; H: 1/2 + x, 1.5 - y, -1/2 + z.]
	Fig. 3. The hydrogen-bonding interactions between adjacent layers in the title complex. [Symmetry codes: A: 0.5 - x, 1.5 - y, 1 - z; B: 1/2 + x, y, 1 - z; C: 1 - x, 1.5 - y, z; D: 0.5 - x,-1/2 + y, 1.5 - z; E: 0.5 - x, 1 - y, z; F: x, 1.5 - y, 1.5 - z; G: 1 - x, 1 - y, 1 - z; H:1/2 + x, 1.5 - y, -1/2 + z.]

4,4'-Diazenediyldipyridinium (4-pyridyldiazenyl)pyridinium octacyanidomolybdate(V) tetrahydrate top

Crystal data top

(C₁₀H₁₀N₄)(C₁₀H₉N₄)[Mo(CN)₈]·4H₂O	F(000) = 1524
M_r = 747.60	D_x = 1.547 Mg m⁻³
Orthorhombic, Ccca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2b 2bc	Cell parameters from 13328 reflections
a = 16.259 (5) Å	θ = 2.4–27.5°
b = 12.787 (4) Å	µ = 0.47 mm⁻¹
c = 15.442 (5) Å	T = 291 K
V = 3210.5 (18) Å³	Block, pale yellow
Z = 4	0.28 × 0.26 × 0.24 mm

Data collection top

Bruker SMART APEX CCD diffractometer	1851 independent reflections
Radiation source: fine-focus sealed tube	1540 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.050
ϕ and ω scans	θ_max = 27.6°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −21→21
T_min = 0.879, T_max = 0.895	k = −16→16
13328 measured reflections	l = −19→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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.065	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0235P)² + 2.9147P] where P = (F_o² + 2F_c²)/3
1851 reflections	(Δ/σ)_max < 0.001
121 parameters	Δρ_max = 0.52 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

(C₁₀H₁₀N₄)(C₁₀H₉N₄)[Mo(CN)₈]·4H₂O	V = 3210.5 (18) Å³
M_r = 747.60	Z = 4
Orthorhombic, Ccca	Mo Kα radiation
a = 16.259 (5) Å	µ = 0.47 mm⁻¹
b = 12.787 (4) Å	T = 291 K
c = 15.442 (5) Å	0.28 × 0.26 × 0.24 mm

Data collection top

Bruker SMART APEX CCD diffractometer	1851 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	1540 reflections with I > 2σ(I)
T_min = 0.879, T_max = 0.895	R_int = 0.050
13328 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.065	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.52 e Å⁻³
1851 reflections	Δρ_min = −0.28 e Å⁻³
121 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)
C1	0.39870 (13)	0.84531 (17)	0.79366 (15)	0.0382 (5)
C2	0.45460 (14)	0.83539 (19)	0.63923 (15)	0.0427 (5)
C3	0.41341 (15)	0.62509 (19)	0.31466 (17)	0.0461 (6)
C4	0.43896 (15)	0.63527 (19)	0.40018 (17)	0.0447 (6)
H4	0.4948	0.6385	0.4132	0.054*
C5	0.38109 (14)	0.64066 (18)	0.46624 (17)	0.0450 (6)
H5	0.3982	0.6474	0.5234	0.054*
C6	0.27215 (16)	0.62570 (19)	0.36140 (16)	0.0464 (6)
H6	0.2163	0.6225	0.3484	0.056*
C7	0.33002 (14)	0.62029 (19)	0.29530 (16)	0.0441 (6)
H7	0.3129	0.6135	0.2381	0.053*
Mo1	0.5000	0.7500	0.7500	0.02552 (10)
N1	0.34570 (12)	0.89415 (16)	0.81824 (14)	0.0468 (5)
N2	0.43040 (13)	0.87856 (16)	0.57871 (13)	0.0462 (5)
N3	0.29771 (12)	0.63591 (16)	0.44687 (13)	0.0437 (5)
H3A	0.262 (2)	0.639 (3)	0.488 (2)	0.052*	0.75
N4	0.46326 (12)	0.62255 (16)	0.24043 (15)	0.0495 (5)
O1	0.17847 (11)	0.59099 (14)	0.56028 (11)	0.0457 (4)
H1A	0.1323 (19)	0.593 (2)	0.535 (2)	0.069*
H1B	0.1865 (18)	0.530 (2)	0.5803 (19)	0.069*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0371 (11)	0.0422 (12)	0.0353 (12)	0.0130 (9)	−0.0141 (9)	−0.0110 (9)
C2	0.0442 (13)	0.0452 (13)	0.0387 (13)	0.0103 (10)	−0.0093 (10)	0.0096 (10)
C3	0.0477 (13)	0.0468 (14)	0.0438 (14)	0.0125 (10)	0.0088 (11)	0.0055 (11)
C4	0.0376 (11)	0.0457 (13)	0.0510 (15)	0.0007 (9)	0.0096 (11)	0.0065 (11)
C5	0.0437 (13)	0.0476 (13)	0.0436 (14)	0.0068 (10)	0.0092 (11)	0.0120 (11)
C6	0.0499 (13)	0.0449 (13)	0.0443 (14)	0.0183 (10)	0.0102 (11)	−0.0136 (10)
C7	0.0453 (13)	0.0482 (14)	0.0388 (14)	0.0139 (10)	−0.0010 (11)	0.0019 (11)
Mo1	0.02788 (16)	0.02590 (16)	0.02278 (16)	0.000	0.000	0.000
N1	0.0505 (12)	0.0483 (11)	0.0417 (12)	0.0182 (9)	−0.0095 (9)	−0.0131 (9)
N2	0.0595 (13)	0.0422 (11)	0.0371 (11)	0.0099 (9)	−0.0119 (10)	0.0020 (9)
N3	0.0438 (11)	0.0452 (11)	0.0420 (12)	0.0206 (9)	0.0038 (9)	−0.0123 (9)
N4	0.0492 (10)	0.0498 (11)	0.0496 (13)	0.0047 (9)	0.0063 (11)	−0.0067 (10)
O1	0.0429 (9)	0.0484 (10)	0.0459 (11)	0.0129 (8)	0.0064 (8)	0.0155 (8)

Geometric parameters (Å, º) top

C1—N1	1.130 (3)	C6—H6	0.9300
C1—Mo1	2.157 (2)	C7—H7	0.9300
C2—N2	1.155 (3)	Mo1—C1ⁱ	2.157 (2)
C2—Mo1	2.159 (2)	Mo1—C1ⁱⁱ	2.157 (2)
C3—C7	1.390 (3)	Mo1—C1ⁱⁱⁱ	2.157 (2)
C3—C4	1.391 (4)	Mo1—C2ⁱⁱⁱ	2.159 (2)
C3—N4	1.404 (3)	Mo1—C2ⁱⁱ	2.159 (2)
C4—C5	1.389 (3)	Mo1—C2ⁱ	2.159 (2)
C4—H4	0.9300	N3—H3A	0.86 (4)
C5—N3	1.390 (3)	N4—N4^iv	1.231 (4)
C5—H5	0.9300	O1—H1A	0.85 (3)
C6—N3	1.390 (3)	O1—H1B	0.85 (3)
C6—C7	1.390 (3)

N1—C1—Mo1	178.5 (2)	C1ⁱⁱ—Mo1—C2ⁱⁱⁱ	77.12 (10)
N2—C2—Mo1	178.1 (2)	C1ⁱⁱⁱ—Mo1—C2ⁱⁱⁱ	72.59 (9)
C7—C3—C4	120.0 (2)	C1ⁱ—Mo1—C2	77.12 (10)
C7—C3—N4	112.7 (2)	C1—Mo1—C2	72.59 (9)
C4—C3—N4	127.2 (2)	C1ⁱⁱ—Mo1—C2	74.20 (9)
C5—C4—C3	120.0 (2)	C1ⁱⁱⁱ—Mo1—C2	142.59 (9)
C5—C4—H4	120.0	C2ⁱⁱⁱ—Mo1—C2	75.23 (13)
C3—C4—H4	120.0	C1ⁱ—Mo1—C2ⁱⁱ	142.59 (9)
C4—C5—N3	120.0 (2)	C1—Mo1—C2ⁱⁱ	74.20 (9)
C4—C5—H5	120.0	C1ⁱⁱ—Mo1—C2ⁱⁱ	72.59 (9)
N3—C5—H5	120.0	C1ⁱⁱⁱ—Mo1—C2ⁱⁱ	77.12 (10)
N3—C6—C7	120.0 (2)	C2ⁱⁱⁱ—Mo1—C2ⁱⁱ	140.02 (13)
N3—C6—H6	120.0	C2—Mo1—C2ⁱⁱ	119.25 (14)
C7—C6—H6	120.0	C1ⁱ—Mo1—C2ⁱ	72.59 (9)
C3—C7—C6	120.0 (2)	C1—Mo1—C2ⁱ	77.12 (10)
C3—C7—H7	120.0	C1ⁱⁱ—Mo1—C2ⁱ	142.59 (9)
C6—C7—H7	120.0	C1ⁱⁱⁱ—Mo1—C2ⁱ	74.20 (9)
C1ⁱ—Mo1—C1	80.44 (12)	C2ⁱⁱⁱ—Mo1—C2ⁱ	119.25 (14)
C1ⁱ—Mo1—C1ⁱⁱ	143.57 (12)	C2—Mo1—C2ⁱ	140.02 (13)
C1—Mo1—C1ⁱⁱ	111.19 (13)	C2ⁱⁱ—Mo1—C2ⁱ	75.23 (13)
C1ⁱ—Mo1—C1ⁱⁱⁱ	111.19 (13)	C5—N3—C6	120.0 (2)
C1—Mo1—C1ⁱⁱⁱ	143.57 (12)	C5—N3—H3A	120 (2)
C1ⁱⁱ—Mo1—C1ⁱⁱⁱ	80.44 (12)	C6—N3—H3A	120 (2)
C1ⁱ—Mo1—C2ⁱⁱⁱ	74.20 (9)	N4^iv—N4—C3	111.4 (3)
C1—Mo1—C2ⁱⁱⁱ	142.59 (9)	H1A—O1—H1B	109 (3)

Symmetry codes: (i) x, −y+3/2, −z+3/2; (ii) −x+1, y, −z+3/2; (iii) −x+1, −y+3/2, z; (iv) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1	0.86 (4)	1.86 (4)	2.675 (3)	157 (3)
O1—H1A···N2^v	0.85 (3)	2.06 (3)	2.809 (3)	147 (3)
O1—H1B···N1^vi	0.85 (3)	2.40 (3)	3.164 (3)	150 (3)

Symmetry codes: (v) −x+1/2, −y+3/2, −z+1; (vi) −x+1/2, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	(C₁₀H₁₀N₄)(C₁₀H₉N₄)[Mo(CN)₈]·4H₂O
M_r	747.60
Crystal system, space group	Orthorhombic, Ccca
Temperature (K)	291
a, b, c (Å)	16.259 (5), 12.787 (4), 15.442 (5)
V (Å³)	3210.5 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.47
Crystal size (mm)	0.28 × 0.26 × 0.24

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.879, 0.895
No. of measured, independent and observed [I > 2σ(I)] reflections	13328, 1851, 1540
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.065, 1.06
No. of reflections	1851
No. of parameters	121
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.52, −0.28

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1	0.86 (4)	1.86 (4)	2.675 (3)	157 (3)
O1—H1A···N2ⁱ	0.85 (3)	2.06 (3)	2.809 (3)	147 (3)
O1—H1B···N1ⁱⁱ	0.85 (3)	2.40 (3)	3.164 (3)	150 (3)

Symmetry codes: (i) −x+1/2, −y+3/2, −z+1; (ii) −x+1/2, y−1/2, −z+3/2.

Acknowledgements

The work is supported by the University Natural Science Foundation of Jiangsu Province (No. 07KJB150030).

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

4,4′-Diazenediyldipyridinium (4-pyridyldiazen­yl)pyridinium octa­cyanidomolyb­date(V) tetra­hydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

4,4′-Diazenediyldipyridinium (4-pyridyldiazenyl)pyridinium octacyanidomolybdate(V) tetrahydrate