catena-Poly[2-methyl­pyridinium [tungstate-di-μ-selenido-silver-di-μ-selenido] 2-methyl­pyridine monosolvate]

Zhou, L.-J.; Shi, H.-T.; Xu, C.; Chen, Q.; Zhang, Q.-F.

doi:10.1107/S1600536813028213

metal-organic compounds

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catena-Poly[2-methylpyridinium [tungstate-di-μ-selenido-silver-di-μ-selenido] 2-methylpyridine monosolvate]

Lu-Jun Zhou,^a Hua-Tian Shi,^b Chao Xu,^b Qun Chen ^a and Qian-Feng Zhang ^b,^a ^*

^aDepartment of Applied Chemistry, School of Petrochemical Engineering, Changzhou University, Jiangsu 213164, People's Republic of China, and ^bInstitute of Molecular Engineering and Applied Chemistry, Anhui University of Technology, Ma'anshan, Anhui 243002, People's Republic of China
^*Correspondence e-mail: zhangqf@ahut.edu.cn

(Received 7 October 2013; accepted 14 October 2013; online 19 October 2013)

The title compound, {(C₆H₈N)[AgWSe₄]·C₆H₇N}_n, consists of anionic [WAgSe₄]_n chains, 2-methylpyridinium cations and neutral 2-methylpyridine molecules. The Se atoms bridge the Ag and W atoms, forming a polymeric chain extending along the b-axis direction. Both the Ag and W atoms are located on a twofold rotation axis and each metal atom is coordinated by four Se atoms in distorted tetrahedral geometry. In the crystal, the 2-methylpyridinium cation and 2-methylpyridine molecule are linked via N—H⋯N hydrogen bonding. Weak C—H⋯Se interactions link the organic components and polymeric anions into a three-dimensional architecture.

CCDC reference: 938862

Related literature

For applications of compounds with [M,M′Se₄] anions (M,M′ = transition metals), see: Zhang et al. (2002 , 2006 ). For related structures, see: Huang et al. (1997 ); Lang et al. (1993 ); Müller et al. (1983 ); Yu et al. (1998 ); Dai et al. (2007 ); Zhang et al. (2000 ).

Experimental

Crystal data

(C₆H₈N)[AgWSe₄]·C₆H₇N
M_r = 794.82
Monoclinic, P 2/c
a = 7.859 (2) Å
b = 5.9448 (15) Å
c = 19.830 (5) Å
β = 100.962 (3)°
V = 909.5 (4) Å³
Z = 2
Mo Kα radiation
μ = 15.39 mm⁻¹
T = 296 K
0.15 × 0.12 × 0.03 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.206, T_max = 0.655
5398 measured reflections
2051 independent reflections
1565 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.078
S = 0.97
2051 reflections
93 parameters
H-atom parameters constrained
Δρ_max = 0.86 e Å⁻³
Δρ_min = −1.06 e Å⁻³

Table 1
Selected bond lengths (Å)

W1—Se1	2.3347 (9)
W1—Se2	2.3379 (9)
Ag1—Se1ⁱ	2.6224 (11)
Ag1—Se2	2.6210 (10)
Symmetry code: (i) x, y+1, z.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯N1ⁱⁱ	0.86	1.93	2.786 (12)	172
C1—H1⋯Se1	0.93	2.96	3.732 (8)	141
C4—H4⋯Se1ⁱⁱⁱ	0.93	2.90	3.832 (8)	176
Symmetry codes: (ii) -x, -y+1, -z+1; (iii) $[x, -y, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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

CCDC reference: 938862

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813028213/xu5746sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813028213/xu5746Isup2.hkl

checkCIF report

Comment top

Tetraselenometalates [MSe₄]^2- (M =Mo, W) have been extensively used in the synthesis of heterselenometallic clusters with third-order nonlinear properties (Zhang et al., 2002). Of special which argentoselenometallic clusters are of good photostability and relatively stable optical limiting effects (Zhang et al., 2006). It has been found that the assembling of [MS₄]^2- (M =Mo, W) and Ag⁺ is flexible through non-bonding interactions with complementary small molecules (or cations) and the solvent, which can assemble into polymeric heterothiometallic clusters with different configurations, such as single linear, zigzag and helical and double chains (Huang et al., 1997; Lang et al., 1993; Müller et al., 1983; Yu et al., 1998). However, it has been noted that the difficulty in the synthesis of argentoselenometallic clusters is probably due to the low solubility of Ag⁺ species that are involved in the self-assembly with the [MSe₄]^2- (M =Mo, W) anion. It is thus understood that only two examples of structurally characterized argentoselenometallic clusters including one-dimensional linear {[Et₄N][(µ-WSe₄)Ag]}_n (Dai et al., 2007) and helical {[La(Me₂SO)₈][(µ₃-WSe₄)₃Ag₃]}_n (Zhang et al., 2000) have been appeared up to date. The one-dimensional chain structure of the title heteroselenometallic polymer {[(2-MepyH)(2-Mepy)][(µ-WSe₄)Ag]}_n is herein described as an addition of this family.

The title heteroselenometallic complex crystallizes in the monoclinic with P2/c space group. An analogous heterothiometallic complex, {[\>a-MepyH][MoS₄Ag]}_n, has been reported, which crystallizes in a monoclinic Pc space group (Lang et al., 1993). The structure determination shows that the title heteroselenometallic complex consists of [(2-MepyH)(2-Mepy)]₊ (py = pyridine) cations with the N—H···N hydrogen bonds and polymeric linear chain of [(µ-WSe₄)Ag]^- anions, as shown in Fig. 1. The anion chain is composed of extended rhombic networks of co-planar [Ag(µ-Se₂)W] units and the neighbouring rhombi in the chain are alternately almost perpendicular to each other. Both metal atoms display tetrahedron coordination in a selenium-rich environment, comparatively, the coordination geometry of the silver atoms (Se—Ag—Se: 97.67 (5)—115.91 (3)°) is more distorted than the tungsten atoms (Se—W—Se: 106.25 (3)—115.47 (5)°). The chain has a straight linear configuration with an Ag—W—Ag angle of 180°. The average W—µ-Se and Ag—µ-Se bond lengths are 2.3363 (9) and 2.6217 (10) Å, respectively. The average W···Ag distance of 2.9725 (11) Å in the title heteroselenometallic complex is comparable to those in {[Et₄N][(µ-WSe₄)Ag]}_n (av. 3.0169 (2) Å) (Dai et al., 2007), {[La(Me₂SO)₈][(µ₃-WSe₄)₃Ag₃]}_n (av. 3.0038 (12) Å) (Zhang, et al., 2000), and [(µ-WSe₄)(AgPPh₃){Ag(PPh₃)₂}] (av. 2.996 (1) Å) (Zhang et al., 2002). The hydrogen-bonding interactions exist between the nitrogen atom of pyridinium caion and the nitrogen atom of the pyridine molecule, forming a molecular [(2-MepyH)(2-Mepy)]⁺ cation with the N—H···N distance and angle of 2.786 (12) Å and 171.9 (3)°, respectively. Relatively weak interactions exist between organic cations and polymeric anions via the C—H···Se hydrogen-bonds with the C—H···Se distance and angle of 3.731 (2) Å and 141.9 (3)°, respectively, as shown in Fig. 1.

Related literature top

For applications of tetraselenometal compounds, see: Zhang et al. (2002, 2006). For related structures, see: Huang et al. (1997); Lang et al. (1993); Müller et al. (1983); Yu et al. (1998); Dai et al. (2007); Zhang et al. (2000).

Experimental top

A solution of AgNO₃ (42.5 mg, 0.25 mmol) in MeCN (5 ml) was added dropwise to a solution of [Et₄N]₂[WSe₄] (190 mg, 0.25 mmol) in DMF (5 ml). The mixture was stirred for 30 min at room temperature, resulting in a large amount of black precipitate. Upon addition of 2 ml 2-picoline solution, the black precipitate was re-dissolved. The resultant solution was stirred for additional 30 min at room temperature and filtered to afford a dark red filtrate. Dark-red prism crystals of the title complex were obtained after allowing the filtrate to stand at room temperature for three days. Anal. Calc. for C₁₂H₁₅N₂Se₄WAg: C, 18.13; H, 1.90; N, 3.53%. Found: C, 18.05; H, 1.87; N, 3.49%.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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. A perspective view of molecular structure of heteroselenometallic polymeric complex {[(2-MepyH)(2-Mepy)][(µ-WSe₄)Ag]}_n. The ellipsoids are drawn at the 50% probability level. Hydrogen bonds are shown in the dash lines.

catena-Poly[2-methylpyridinium [tungstate-di-µ-selenido-silver-di-µ-selenido] 2-methylpyridine monosolvate] top

Crystal data top

(C₆H₈N)[AgWSe₄]·C₆H₇N	F(000) = 716
M_r = 794.82	D_x = 2.902 Mg m⁻³
Monoclinic, P2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yc	Cell parameters from 1243 reflections
a = 7.859 (2) Å	θ = 2.6–24.5°
b = 5.9448 (15) Å	µ = 15.39 mm⁻¹
c = 19.830 (5) Å	T = 296 K
β = 100.962 (3)°	Prism, dark red
V = 909.5 (4) Å³	0.15 × 0.12 × 0.03 mm
Z = 2

Data collection top

Bruker APEXII CCD area-detector diffractometer	2051 independent reflections
Radiation source: fine-focus sealed tube	1565 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
phi and ω scans	θ_max = 27.4°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −10→6
T_min = 0.206, T_max = 0.655	k = −7→7
5398 measured reflections	l = −24→25

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.078	H-atom parameters constrained
S = 0.97	w = 1/[σ²(F_o²) + (0.0357P)²] where P = (F_o² + 2F_c²)/3
2051 reflections	(Δ/σ)_max = 0.001
93 parameters	Δρ_max = 0.86 e Å⁻³
0 restraints	Δρ_min = −1.06 e Å⁻³

Crystal data top

(C₆H₈N)[AgWSe₄]·C₆H₇N	V = 909.5 (4) Å³
M_r = 794.82	Z = 2
Monoclinic, P2/c	Mo Kα radiation
a = 7.859 (2) Å	µ = 15.39 mm⁻¹
b = 5.9448 (15) Å	T = 296 K
c = 19.830 (5) Å	0.15 × 0.12 × 0.03 mm
β = 100.962 (3)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	2051 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1565 reflections with I > 2σ(I)
T_min = 0.206, T_max = 0.655	R_int = 0.041
5398 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.078	H-atom parameters constrained
S = 0.97	Δρ_max = 0.86 e Å⁻³
2051 reflections	Δρ_min = −1.06 e Å⁻³
93 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)
W1	0.5000	0.30930 (6)	0.7500	0.03027 (13)
Ag1	0.5000	0.80929 (13)	0.7500	0.0524 (2)
Se1	0.24423 (10)	0.09964 (13)	0.72794 (4)	0.0417 (2)
Se2	0.50518 (11)	0.51956 (12)	0.65078 (4)	0.0434 (2)
N1	0.0998 (7)	0.3192 (10)	0.4854 (3)	0.0389 (14)
H1N	0.0423	0.4382	0.4914	0.047*	0.50
C1	0.1778 (10)	0.1984 (14)	0.5389 (4)	0.0478 (19)
H1	0.1711	0.2486	0.5828	0.057*
C2	0.2676 (11)	0.0041 (13)	0.5329 (5)	0.053 (2)
H2	0.3163	−0.0786	0.5716	0.064*
C3	0.2838 (12)	−0.0653 (16)	0.4690 (5)	0.062 (2)
H3	0.3473	−0.1938	0.4635	0.075*
C4	0.2043 (11)	0.0586 (15)	0.4116 (4)	0.053 (2)
H4	0.2133	0.0114	0.3677	0.064*
C5	0.1125 (10)	0.2507 (14)	0.4203 (4)	0.0447 (19)
C6	0.0282 (12)	0.3915 (15)	0.3622 (4)	0.059 (2)
H6A	0.0500	0.3291	0.3200	0.088*
H6B	0.0741	0.5414	0.3678	0.088*
H6C	−0.0945	0.3955	0.3610	0.088*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
W1	0.0371 (2)	0.0225 (2)	0.0303 (2)	0.000	0.00409 (16)	0.000
Ag1	0.0704 (6)	0.0280 (4)	0.0565 (5)	0.000	0.0061 (5)	0.000
Se1	0.0412 (4)	0.0389 (4)	0.0425 (4)	−0.0057 (3)	0.0020 (3)	0.0049 (3)
Se2	0.0587 (5)	0.0342 (4)	0.0377 (4)	−0.0027 (4)	0.0101 (4)	0.0051 (3)
N1	0.035 (3)	0.046 (4)	0.035 (3)	−0.005 (3)	0.004 (3)	−0.005 (3)
C1	0.049 (5)	0.060 (5)	0.034 (4)	−0.001 (4)	0.005 (4)	−0.005 (4)
C2	0.056 (5)	0.039 (5)	0.064 (5)	0.005 (4)	0.010 (5)	0.010 (4)
C3	0.053 (5)	0.053 (6)	0.089 (7)	0.004 (5)	0.032 (5)	−0.007 (5)
C4	0.052 (5)	0.059 (6)	0.051 (5)	−0.009 (5)	0.016 (4)	−0.015 (4)
C5	0.040 (4)	0.054 (5)	0.040 (4)	−0.008 (4)	0.007 (3)	−0.004 (4)
C6	0.062 (6)	0.078 (6)	0.033 (4)	−0.006 (5)	−0.001 (4)	−0.008 (4)

Geometric parameters (Å, º) top

W1—Se1	2.3347 (9)	N1—H1N	0.8600
W1—Se1ⁱ	2.3347 (9)	C1—C2	1.371 (10)
W1—Se2ⁱ	2.3379 (9)	C1—H1	0.9300
W1—Se2	2.3379 (9)	C2—C3	1.361 (12)
W1—Ag1	2.9723 (11)	C2—H2	0.9300
W1—Ag1ⁱⁱ	2.9725 (11)	C3—C4	1.400 (12)
Ag1—Se1ⁱⁱⁱ	2.6224 (11)	C3—H3	0.9300
Ag1—Se1^iv	2.6224 (11)	C4—C5	1.380 (11)
Ag1—Se2	2.6210 (10)	C4—H4	0.9300
Ag1—Se2ⁱ	2.6210 (10)	C5—C6	1.475 (11)
Ag1—W1^iv	2.9725 (11)	C6—H6A	0.9600
N1—C1	1.330 (9)	C6—H6B	0.9600
N1—C5	1.376 (9)	C6—H6C	0.9600

Se1—W1—Se1ⁱ	115.47 (5)	Se1^iv—Ag1—W1^iv	48.84 (2)
Se1—W1—Se2ⁱ	106.92 (3)	W1—Ag1—W1^iv	180.0
Se1ⁱ—W1—Se2ⁱ	106.25 (3)	W1—Se1—Ag1ⁱⁱ	73.43 (3)
Se1—W1—Se2	106.25 (3)	W1—Se2—Ag1	73.40 (3)
Se1ⁱ—W1—Se2	106.92 (3)	C1—N1—C5	119.0 (6)
Se2ⁱ—W1—Se2	115.36 (4)	C1—N1—H1N	120.5
Se1—W1—Ag1	122.27 (2)	C5—N1—H1N	120.5
Se1ⁱ—W1—Ag1	122.27 (2)	N1—C1—C2	123.5 (7)
Se2ⁱ—W1—Ag1	57.68 (2)	N1—C1—H1	118.2
Se2—W1—Ag1	57.68 (2)	C2—C1—H1	118.2
Se1—W1—Ag1ⁱⁱ	57.73 (2)	C3—C2—C1	118.5 (8)
Se1ⁱ—W1—Ag1ⁱⁱ	57.73 (2)	C3—C2—H2	120.7
Se2ⁱ—W1—Ag1ⁱⁱ	122.32 (2)	C1—C2—H2	120.7
Se2—W1—Ag1ⁱⁱ	122.32 (2)	C2—C3—C4	119.4 (8)
Ag1—W1—Ag1ⁱⁱ	180.000 (1)	C2—C3—H3	120.3
Se2—Ag1—Se2ⁱ	97.84 (4)	C4—C3—H3	120.3
Se2—Ag1—Se1ⁱⁱⁱ	115.91 (3)	C5—C4—C3	119.8 (7)
Se2ⁱ—Ag1—Se1ⁱⁱⁱ	115.35 (3)	C5—C4—H4	120.1
Se2—Ag1—Se1^iv	115.35 (3)	C3—C4—H4	120.1
Se2ⁱ—Ag1—Se1^iv	115.91 (3)	N1—C5—C4	119.7 (7)
Se1ⁱⁱⁱ—Ag1—Se1^iv	97.67 (5)	N1—C5—C6	117.6 (7)
Se2—Ag1—W1	48.92 (2)	C4—C5—C6	122.7 (7)
Se2ⁱ—Ag1—W1	48.92 (2)	C5—C6—H6A	109.5
Se1ⁱⁱⁱ—Ag1—W1	131.16 (2)	C5—C6—H6B	109.5
Se1^iv—Ag1—W1	131.16 (2)	H6A—C6—H6B	109.5
Se2—Ag1—W1^iv	131.08 (2)	C5—C6—H6C	109.5
Se2ⁱ—Ag1—W1^iv	131.08 (2)	H6A—C6—H6C	109.5
Se1ⁱⁱⁱ—Ag1—W1^iv	48.84 (2)	H6B—C6—H6C	109.5

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N1^v	0.86	1.93	2.786 (12)	172
C1—H1···Se1	0.93	2.96	3.732 (8)	141
C4—H4···Se1^vi	0.93	2.90	3.832 (8)	176

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

Selected bond lengths (Å) top

W1—Se1	2.3347 (9)	Ag1—Se1ⁱ	2.6224 (11)
W1—Se2	2.3379 (9)	Ag1—Se2	2.6210 (10)

Symmetry code: (i) x, y+1, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N1ⁱⁱ	0.86	1.93	2.786 (12)	172
C1—H1···Se1	0.93	2.96	3.732 (8)	141
C4—H4···Se1ⁱⁱⁱ	0.93	2.90	3.832 (8)	176

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

Acknowledgements

This work was supported by the Natural Science Foundation of China (20871002) and the Program for New Century Excellent Talents in Universities of China (NCET-08–0618). QFZ is grateful to the State Key Laboratory of Coordination Chemistry at Nanjing University for assistance with the data collection.

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catena-Poly[2-methyl­pyridinium [tungstate-di-μ-selenido-silver-di-μ-selenido] 2-methyl­pyridine monosolvate]

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

catena-Poly[2-methylpyridinium [tungstate-di-μ-selenido-silver-di-μ-selenido] 2-methylpyridine monosolvate]