Poly[bis­{3,3′-[(biphenyl-4,4′-di­yl)dimethyl­ene]diimidazol-1-ium} γ-octa­molybdate(VI)]

Liu, H.; Su, L.; Wang, L.; Li, W.

doi:10.1107/S1600536810010111

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Pages m443-m444

doi:10.1107/S1600536810010111

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Poly[bis{3,3′-[(biphenyl-4,4′-diyl)dimethylene]diimidazol-1-ium} γ-octamolybdate(VI)]

Hongsheng Liu,^a ^* Lianjiang Su,^a Limin Wang ^a and Weihong Li ^a

^aSchool of Chemistry and Chemical Engineering, Daqing Normal University, Daqing 163712, People's Republic of China
^*Correspondence e-mail: liuhsdqnu@yahoo.cn

(Received 28 February 2010; accepted 17 March 2010; online 24 March 2010)

In the title compound, {(C₂₀H₂₀N₄)₂[Mo₈O₂₆]}_n, the asymmetric unit contains half of an [Mo₈O₂₆]⁴⁻ anion and one 3,3′-[(biphenyl-4,4′-diyl)dimethylene]diimidazol-1-ium dication. In the anion, four distorted [MoO₆] octahedra are connected via edge-sharing, forming an [Mo₄O₁₃]²⁻ building block, composed of Mo—O(t), Mo—O(μ2), Mo—O(μ3) and Mo—O(μ4) units, with Mo—O distances ranging from 1.6858 (15) to 2.4785 (13) Å. The γ-type [Mo₈O₂₆]⁴⁻ anion is completed by crystallographic inversion symmetry and is linked into an infinite chain along [100] by corner-sharing. The anionic chains and the cations are joined by N—H⋯O hydrogen bonds, generating layers extending parallel to (001).

Related literature

For backgroud to polyoxomolybdates, see: Zaworotko (1998 ); Hong & Do (1998 ); Carlucci et al. (2003 ); Moulton & Zaworotko (2001 ). For a similar structure, see: Modec et al. (2003 ). For the synthesis of 3,3′-(p-biphenylenedimethylene)diimidazole, see: Fei et al. (2000 ).

Experimental

Crystal data

(C₂₀H₂₀N₄)₂[Mo₈O₂₆]
M_r = 1816.32
Monoclinic, P 2₁ /n
a = 9.6460 (4) Å
b = 17.3370 (6) Å
c = 16.6620 (6) Å
β = 106.145 (1)°
V = 2676.54 (17) Å³
Z = 2
Mo Kα radiation
μ = 1.90 mm⁻¹
T = 293 K
0.28 × 0.27 × 0.23 mm

Data collection

Bruker APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.559, T_max = 0.616
16209 measured reflections
6405 independent reflections
5716 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.021
wR(F²) = 0.051
S = 1.03
6405 reflections
378 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.01 e Å⁻³
Δρ_min = −0.57 e Å⁻³

Table 1
Selected bond lengths (Å)

Mo3—O7	1.6929 (15)
Mo3—O8	1.7365 (14)
Mo3—O6	1.8705 (13)
Mo3—O9	1.9774 (13)
Mo3—O3	2.1723 (14)
Mo3—O9ⁱ	2.4785 (13)
Mo1—O1	1.6958 (16)
Mo1—O2	1.6996 (15)
Mo1—O13	1.8952 (13)
Mo1—O3	1.9789 (13)
Mo1—O9	2.2882 (14)
Mo1—O8ⁱ	2.4032 (14)
Mo2—O10	1.6858 (15)
Mo2—O11	1.7665 (15)
Mo2—O12	1.8428 (14)
Mo2—O13	2.0340 (14)
Mo2—O9	2.0869 (12)
Mo2—O6ⁱ	2.4210 (14)
Mo4—O5	1.6870 (16)
Mo4—O4	1.7163 (16)
Mo4—O12ⁱⁱ	1.9289 (14)
Mo4—O3	1.9958 (13)
Mo4—O6	2.1806 (14)
Mo4—O11ⁱ	2.2857 (15)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x+1, y, z.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O4ⁱⁱⁱ	0.92 (3)	1.96 (3)	2.854 (4)	165 (3)
N4—H4N⋯O13^iv	0.92 (3)	1.77 (2)	2.658 (3)	163 (3)
Symmetry codes: (iii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iv) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Crystal Impact, 2008 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810010111/wm2312sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810010111/wm2312Isup2.hkl

checkCIF report

Comment top

Polyoxometalates of molybdenum are an interesting class of metal-oxido compounds. Recently, many organic-inorganic hybrids have been reported (Zaworotko, 1998; Hong & Do, 1998) because they possess unique architectures and their cooperative functional properties have attracted considerable attention (Carlucci et al., 2003; Moulton & Zaworotko, 2001). In this paper, we present the hydrothermal synthesis and crystal structure of the title compound, (C₂₀H₂₀N₄)₂[Mo₈O₂₆], (I), based on the protonated 3,3'-(p-biphenylenedimethylene)diimidazole ligand (hereafter L), and a γ-type [Mo₈O₂₆]^4- POM anion.

In the structure of compound (I), the asymmetric unit contains half of a γ-type [Mo₈O₂₆]^4- anion, which is completed by inversion symmetry, and one H₂L²⁺ cation (Fig. 1). The four unique [MoO₆] octahedra are considerably distorted. They are connected via edge-sharing to form the [Mo₄O₁₃]^2- unit, which is further linked together by edge-sharing to give rise to γ-[Mo₈O₂₆]^4- octamolybdate units. Four sets of Mo-O distances, corresponding to their function as Mo-O(t), Mo-O(µ2), Mo-O(µ3) and Mo-O(µ4) units, are observed and range from 1.6858 (15) Å to 2.4785 (13) Å. These distances are similar to those in comparable structures (Modec et al., 2003). The γ-octamolybdate units are finally linked together through sharing common vertices to form infinite chains extending along [100] (Fig. 2). These chains are linked through N—H···O hydrogen bonding to generate layers extending parallel to (001) (Fig. 3).

Related literature top

For backgroud to polyoxomolybdates, see: Zaworotko (1998); Hong & Do (1998); Carlucci et al. (2003); Moulton & Zaworotko (2001). For a similar structure, see: Modec et al. (2003). For the synthesis of 3,3'-(p-biphenylenedimethylene)diimidazole, see: Fei et al. (2000).

Experimental top

A mixture of (NH₄)₆Mo₇O₂₄^.4H₂O (0.12 g, 0.1 mmol), L (0.031 g, 0.2 mmol) (Fei et al., 2000) and H₂O (10 ml) was adjusted with HCl (6M) to pH = 4-5. Then the mixture was placed in a 23 ml Teflon-lined stainless steel container. The container was heated to 423 K and held at that temperature for 72 h, and cooled to room temperature. Colorless crystals were collected in 67% yield.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Crystal Impact, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. A displacement ellipsoids view of the building units of (I), drawn at the 30% probability level.
	Fig. 2. Part of the [Mo₈O₂₆]_n^4n- chain.
	Fig. 3. View of the layer structure formed by N-H···O hydrogen bonds.

Poly[bis{3,3'-[(biphenyl-4,4'-diyl)dimethylene]diimidazol-1-ium} γ-octamolybdate(VI)] top

Crystal data top

(C₂₀H₂₀N₄)₂[Mo₈O₂₆]	F(000) = 1760
M_r = 1816.32	D_x = 2.254 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2yn	Cell parameters from 139 reflections
a = 9.6460 (4) Å	θ = 1.7–28.3°
b = 17.3370 (6) Å	µ = 1.90 mm⁻¹
c = 16.6620 (6) Å	T = 293 K
β = 106.145 (1)°	Block, colorless
V = 2676.54 (17) Å³	0.28 × 0.27 × 0.23 mm
Z = 2

Data collection top

Bruker APEX CCD area-detector diffractometer	6405 independent reflections
Radiation source: fine-focus sealed tube	5716 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ω scans	θ_max = 28.3°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→12
T_min = 0.559, T_max = 0.616	k = −23→23
16209 measured reflections	l = −21→21

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) = 0.051	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0254P)² + 0.027P] where P = (F_o² + 2F_c²)/3
6405 reflections	(Δ/σ)_max = 0.001
378 parameters	Δρ_max = 1.01 e Å⁻³
2 restraints	Δρ_min = −0.57 e Å⁻³

Crystal data top

(C₂₀H₂₀N₄)₂[Mo₈O₂₆]	V = 2676.54 (17) Å³
M_r = 1816.32	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.6460 (4) Å	µ = 1.90 mm⁻¹
b = 17.3370 (6) Å	T = 293 K
c = 16.6620 (6) Å	0.28 × 0.27 × 0.23 mm
β = 106.145 (1)°

Data collection top

Bruker APEX CCD area-detector diffractometer	6405 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	5716 reflections with I > 2σ(I)
T_min = 0.559, T_max = 0.616	R_int = 0.020
16209 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.021	2 restraints
wR(F²) = 0.051	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 1.01 e Å⁻³
6405 reflections	Δρ_min = −0.57 e Å⁻³
378 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Mo3	0.589310 (17)	0.411089 (9)	0.498376 (10)	0.02082 (5)
Mo1	0.363467 (17)	0.472925 (10)	0.320138 (10)	0.02348 (5)
Mo2	0.172190 (17)	0.433192 (10)	0.449319 (11)	0.02298 (5)
Mo4	0.773555 (17)	0.457531 (10)	0.370756 (11)	0.02573 (5)
C8	0.1996 (3)	0.51860 (14)	0.97308 (16)	0.0430 (6)
O11	0.20748 (15)	0.42795 (8)	0.55905 (9)	0.0297 (3)
O7	0.56742 (16)	0.31831 (8)	0.46558 (10)	0.0361 (4)
O8	0.60243 (15)	0.40726 (8)	0.60437 (9)	0.0287 (3)
C14	0.4967 (3)	0.33842 (16)	1.08281 (18)	0.0495 (7)
O9	0.39012 (13)	0.45144 (8)	0.45911 (8)	0.0226 (3)
O2	0.34754 (16)	0.38200 (9)	0.28046 (10)	0.0388 (4)
O4	0.74877 (17)	0.51414 (10)	0.28339 (10)	0.0410 (4)
C7	0.1760 (3)	0.57956 (18)	1.02188 (17)	0.0569 (8)
H7	0.2222	0.5799	1.0789	0.068*
O10	0.17148 (18)	0.33876 (9)	0.42508 (11)	0.0420 (4)
O5	0.76131 (17)	0.36631 (10)	0.33422 (11)	0.0441 (4)
C17	0.6025 (3)	0.27601 (17)	1.1218 (2)	0.0643 (9)
H17A	0.6299	0.2481	1.0781	0.077*
H17B	0.6888	0.2995	1.1578	0.077*
O6	0.77906 (14)	0.43579 (8)	0.50051 (9)	0.0251 (3)
C11	0.3006 (3)	0.45522 (15)	1.01032 (16)	0.0420 (6)
O12	−0.01976 (15)	0.46101 (10)	0.41738 (10)	0.0375 (4)
O13	0.18052 (14)	0.48333 (8)	0.34039 (9)	0.0264 (3)
O3	0.57176 (14)	0.46661 (8)	0.37908 (9)	0.0253 (3)
N2	−0.0262 (2)	0.75613 (12)	0.81224 (14)	0.0502 (6)
C19	0.4540 (3)	0.17163 (17)	1.2659 (2)	0.0614 (8)
H19	0.4247	0.1639	1.3139	0.074*
C18	0.4929 (3)	0.15197 (14)	1.14441 (19)	0.0488 (7)
H18	0.4954	0.1293	1.0942	0.059*
C12	0.4210 (3)	0.46984 (15)	1.07717 (16)	0.0471 (6)
H12	0.4371	0.5196	1.0985	0.057*
N3	0.5424 (2)	0.22120 (11)	1.17101 (14)	0.0443 (5)
C10	0.0366 (3)	0.57963 (16)	0.85391 (17)	0.0501 (7)
H10	−0.0108	0.5790	0.7971	0.060*
C20	0.5186 (3)	0.23459 (16)	1.24635 (19)	0.0596 (8)
H20	0.5426	0.2791	1.2784	0.071*
C6	0.0857 (3)	0.63925 (18)	0.98732 (18)	0.0605 (8)
H6	0.0726	0.6796	1.0213	0.073*
N1	0.1007 (3)	0.84206 (16)	0.7726 (3)	0.0811 (9)
C16	0.2814 (3)	0.37990 (17)	0.9806 (2)	0.0592 (7)
H16	0.2019	0.3682	0.9360	0.071*
C2	0.0738 (3)	0.81019 (17)	0.8382 (2)	0.0602 (8)
H2	0.1175	0.8233	0.8936	0.072*
C4	−0.0864 (3)	0.70583 (17)	0.86535 (18)	0.0559 (7)
H4A	−0.1776	0.6847	0.8322	0.067*
H4B	−0.1054	0.7363	0.9100	0.067*
C15	0.3770 (3)	0.32231 (17)	1.0156 (2)	0.0640 (8)
H15	0.3619	0.2724	0.9944	0.077*
N4	0.4398 (2)	0.12085 (13)	1.20108 (16)	0.0506 (6)
C3	−0.0639 (4)	0.7547 (2)	0.7282 (2)	0.0794 (10)
H3	−0.1323	0.7225	0.6938	0.095*
C5	0.0136 (3)	0.64072 (15)	0.90269 (17)	0.0473 (6)
O1	0.35190 (17)	0.53203 (10)	0.23743 (10)	0.0406 (4)
C13	0.5162 (3)	0.41255 (16)	1.11222 (17)	0.0496 (6)
H13	0.5957	0.4242	1.1569	0.059*
C9	0.1282 (3)	0.52027 (15)	0.88812 (17)	0.0493 (6)
H9	0.1428	0.4805	0.8539	0.059*
C1	0.0152 (5)	0.8082 (2)	0.7031 (3)	0.0932 (12)
H1	0.0120	0.8199	0.6482	0.112*
H4N	0.396 (3)	0.0737 (9)	1.1971 (17)	0.057 (8)*
H1N	0.163 (3)	0.8830 (14)	0.777 (2)	0.102 (14)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mo3	0.01444 (8)	0.02311 (9)	0.02444 (10)	−0.00012 (6)	0.00463 (6)	0.00029 (7)
Mo1	0.01472 (8)	0.03481 (10)	0.02030 (9)	−0.00007 (7)	0.00384 (6)	−0.00334 (7)
Mo2	0.01459 (8)	0.02982 (9)	0.02530 (10)	−0.00497 (6)	0.00681 (7)	−0.00595 (7)
Mo4	0.01425 (8)	0.03941 (10)	0.02425 (10)	−0.00371 (7)	0.00657 (7)	−0.00845 (8)
C8	0.0415 (14)	0.0504 (14)	0.0407 (14)	−0.0023 (11)	0.0170 (11)	−0.0041 (12)
O11	0.0254 (8)	0.0355 (8)	0.0298 (8)	−0.0068 (6)	0.0105 (6)	−0.0017 (6)
O7	0.0346 (9)	0.0276 (7)	0.0442 (10)	−0.0007 (7)	0.0079 (7)	−0.0045 (7)
O8	0.0253 (7)	0.0331 (8)	0.0274 (8)	−0.0014 (6)	0.0068 (6)	0.0033 (6)
C14	0.0369 (14)	0.0525 (16)	0.0620 (18)	−0.0001 (12)	0.0186 (13)	0.0083 (14)
O9	0.0146 (6)	0.0288 (7)	0.0237 (7)	−0.0016 (5)	0.0045 (5)	−0.0018 (6)
O2	0.0276 (8)	0.0468 (9)	0.0410 (10)	−0.0002 (7)	0.0080 (7)	−0.0174 (8)
O4	0.0357 (9)	0.0605 (11)	0.0289 (9)	−0.0051 (8)	0.0127 (7)	−0.0036 (8)
C7	0.0601 (19)	0.075 (2)	0.0342 (15)	0.0158 (15)	0.0107 (13)	−0.0071 (14)
O10	0.0454 (10)	0.0343 (8)	0.0469 (11)	−0.0085 (8)	0.0140 (8)	−0.0126 (8)
O5	0.0322 (9)	0.0491 (10)	0.0513 (11)	−0.0022 (7)	0.0119 (8)	−0.0216 (8)
C17	0.0440 (17)	0.0597 (18)	0.092 (3)	0.0050 (14)	0.0239 (16)	0.0152 (17)
O6	0.0139 (6)	0.0326 (7)	0.0282 (8)	−0.0001 (5)	0.0047 (5)	−0.0022 (6)
C11	0.0411 (14)	0.0490 (14)	0.0395 (14)	−0.0016 (11)	0.0175 (11)	0.0023 (11)
O12	0.0154 (7)	0.0637 (11)	0.0346 (9)	−0.0039 (7)	0.0088 (6)	−0.0116 (8)
O13	0.0152 (6)	0.0377 (8)	0.0248 (8)	0.0013 (6)	0.0034 (5)	−0.0035 (6)
O3	0.0149 (7)	0.0379 (8)	0.0235 (7)	−0.0012 (6)	0.0061 (5)	−0.0010 (6)
N2	0.0476 (13)	0.0443 (12)	0.0503 (14)	0.0066 (10)	−0.0002 (10)	−0.0195 (11)
C19	0.068 (2)	0.0582 (18)	0.059 (2)	0.0014 (16)	0.0190 (16)	0.0012 (15)
C18	0.0382 (14)	0.0418 (14)	0.0654 (19)	0.0008 (11)	0.0128 (13)	−0.0155 (13)
C12	0.0548 (17)	0.0480 (15)	0.0405 (15)	−0.0017 (13)	0.0166 (13)	−0.0030 (12)
N3	0.0352 (11)	0.0356 (10)	0.0589 (14)	0.0023 (9)	0.0079 (10)	−0.0045 (10)
C10	0.0451 (16)	0.0588 (17)	0.0380 (15)	−0.0015 (13)	−0.0023 (11)	−0.0092 (12)
C20	0.072 (2)	0.0412 (14)	0.062 (2)	−0.0015 (14)	0.0122 (16)	−0.0134 (14)
C6	0.065 (2)	0.071 (2)	0.0432 (17)	0.0190 (16)	0.0125 (14)	−0.0144 (15)
N1	0.066 (2)	0.0483 (16)	0.135 (3)	0.0127 (15)	0.039 (2)	−0.0014 (19)
C16	0.0421 (16)	0.0581 (18)	0.069 (2)	−0.0050 (13)	0.0012 (13)	−0.0070 (15)
C2	0.0354 (15)	0.0547 (17)	0.085 (2)	0.0081 (13)	0.0071 (15)	−0.0322 (17)
C4	0.0434 (16)	0.0637 (18)	0.0559 (18)	0.0078 (13)	0.0058 (13)	−0.0137 (15)
C15	0.0540 (19)	0.0477 (16)	0.084 (2)	−0.0041 (14)	0.0095 (16)	−0.0063 (16)
N4	0.0356 (12)	0.0392 (12)	0.0733 (17)	−0.0051 (10)	0.0089 (11)	−0.0091 (12)
C3	0.116 (3)	0.059 (2)	0.051 (2)	0.000 (2)	0.0034 (19)	−0.0105 (17)
C5	0.0365 (14)	0.0552 (16)	0.0483 (16)	0.0029 (12)	0.0084 (11)	−0.0095 (13)
O1	0.0363 (9)	0.0583 (11)	0.0261 (9)	0.0010 (8)	0.0067 (7)	0.0061 (8)
C13	0.0428 (15)	0.0604 (17)	0.0438 (16)	−0.0044 (13)	0.0091 (12)	0.0008 (13)
C9	0.0518 (16)	0.0482 (15)	0.0462 (16)	−0.0018 (12)	0.0107 (13)	−0.0136 (13)
C1	0.129 (4)	0.078 (3)	0.072 (3)	0.014 (3)	0.027 (3)	0.007 (2)

Geometric parameters (Å, º) top

Mo3—O7	1.6929 (15)	O6—Mo2ⁱ	2.4210 (14)
Mo3—O8	1.7365 (14)	C11—C12	1.390 (4)
Mo3—O6	1.8705 (13)	C11—C16	1.391 (4)
Mo3—O9	1.9774 (13)	O12—Mo4ⁱⁱⁱ	1.9289 (14)
Mo3—O3	2.1723 (14)	N2—C2	1.328 (3)
Mo3—O9ⁱ	2.4785 (13)	N2—C3	1.346 (4)
Mo1—O1	1.6958 (16)	N2—C4	1.472 (4)
Mo1—O2	1.6996 (15)	C19—C20	1.341 (4)
Mo1—O13	1.8952 (13)	C19—N4	1.370 (4)
Mo1—O3	1.9789 (13)	C19—H19	0.9300
Mo1—O9	2.2882 (14)	C18—N4	1.309 (4)
Mo1—O8ⁱ	2.4032 (14)	C18—N3	1.322 (3)
Mo2—O10	1.6858 (15)	C18—H18	0.9300
Mo2—O11	1.7665 (15)	C12—C13	1.369 (4)
Mo2—O12	1.8428 (14)	C12—H12	0.9300
Mo2—O13	2.0340 (14)	N3—C20	1.357 (3)
Mo2—O9	2.0869 (12)	C10—C9	1.373 (4)
Mo2—O6ⁱ	2.4210 (14)	C10—C5	1.390 (4)
Mo4—O5	1.6870 (16)	C10—H10	0.9300
Mo4—O4	1.7163 (16)	C20—H20	0.9300
Mo4—O12ⁱⁱ	1.9289 (14)	C6—C5	1.388 (4)
Mo4—O3	1.9958 (13)	C6—H6	0.9300
Mo4—O6	2.1806 (14)	N1—C2	1.314 (4)
Mo4—O11ⁱ	2.2857 (15)	N1—C1	1.354 (5)
C8—C7	1.390 (3)	N1—H1N	0.92 (3)
C8—C9	1.392 (4)	C16—C15	1.374 (4)
C8—C11	1.485 (4)	C16—H16	0.9300
O11—Mo4ⁱ	2.2857 (15)	C2—H2	0.9300
O8—Mo1ⁱ	2.4032 (14)	C4—C5	1.503 (4)
C14—C13	1.370 (4)	C4—H4A	0.9700
C14—C15	1.396 (4)	C4—H4B	0.9700
C14—C17	1.505 (4)	C15—H15	0.9300
O9—Mo3ⁱ	2.4785 (13)	N4—H4N	0.92 (3)
C7—C6	1.372 (4)	C3—C1	1.339 (5)
C7—H7	0.9300	C3—H3	0.9300
C17—N3	1.475 (3)	C13—H13	0.9300
C17—H17A	0.9700	C9—H9	0.9300
C17—H17B	0.9700	C1—H1	0.9300

O7—Mo3—O8	105.02 (7)	N3—C17—C14	112.3 (2)
O7—Mo3—O6	104.90 (7)	N3—C17—H17A	109.1
O8—Mo3—O6	101.26 (6)	C14—C17—H17A	109.1
O7—Mo3—O9	101.94 (7)	N3—C17—H17B	109.1
O8—Mo3—O9	98.01 (6)	C14—C17—H17B	109.1
O6—Mo3—O9	141.35 (6)	H17A—C17—H17B	107.9
O7—Mo3—O3	98.90 (7)	Mo3—O6—Mo4	105.48 (6)
O8—Mo3—O3	155.88 (6)	Mo3—O6—Mo2ⁱ	108.45 (6)
O6—Mo3—O3	75.10 (6)	Mo4—O6—Mo2ⁱ	97.41 (5)
O9—Mo3—O3	73.69 (5)	C12—C11—C16	117.1 (3)
O7—Mo3—O9ⁱ	177.09 (6)	C12—C11—C8	120.3 (2)
O8—Mo3—O9ⁱ	76.63 (6)	C16—C11—C8	122.6 (3)
O6—Mo3—O9ⁱ	76.95 (5)	Mo2—O12—Mo4ⁱⁱⁱ	162.00 (10)
O9—Mo3—O9ⁱ	75.38 (5)	Mo1—O13—Mo2	112.83 (7)
O3—Mo3—O9ⁱ	79.34 (5)	Mo1—O3—Mo4	147.69 (8)
O1—Mo1—O2	105.42 (8)	Mo1—O3—Mo3	106.78 (6)
O1—Mo1—O13	103.48 (7)	Mo4—O3—Mo3	101.50 (6)
O2—Mo1—O13	99.76 (6)	C2—N2—C3	108.3 (3)
O1—Mo1—O3	105.37 (7)	C2—N2—C4	126.5 (3)
O2—Mo1—O3	96.38 (7)	C3—N2—C4	125.3 (3)
O13—Mo1—O3	141.63 (6)	C20—C19—N4	106.5 (3)
O1—Mo1—O9	152.15 (7)	C20—C19—H19	126.8
O2—Mo1—O9	102.43 (7)	N4—C19—H19	126.8
O13—Mo1—O9	71.54 (5)	N4—C18—N3	108.0 (2)
O3—Mo1—O9	71.09 (5)	N4—C18—H18	126.0
O1—Mo1—O8ⁱ	82.62 (7)	N3—C18—H18	126.0
O2—Mo1—O8ⁱ	171.74 (7)	C13—C12—C11	121.4 (2)
O13—Mo1—O8ⁱ	79.82 (5)	C13—C12—H12	119.3
O3—Mo1—O8ⁱ	79.38 (5)	C11—C12—H12	119.3
O9—Mo1—O8ⁱ	69.54 (5)	C18—N3—C20	109.1 (2)
O10—Mo2—O11	100.65 (8)	C18—N3—C17	124.0 (3)
O10—Mo2—O12	104.37 (8)	C20—N3—C17	126.7 (2)
O11—Mo2—O12	101.62 (7)	C9—C10—C5	121.2 (2)
O10—Mo2—O13	101.52 (7)	C9—C10—H10	119.4
O11—Mo2—O13	154.35 (6)	C5—C10—H10	119.4
O12—Mo2—O13	85.20 (6)	C19—C20—N3	107.1 (3)
O10—Mo2—O9	95.90 (7)	C19—C20—H20	126.4
O11—Mo2—O9	91.54 (6)	N3—C20—H20	126.4
O12—Mo2—O9	153.16 (7)	C7—C6—C5	121.4 (3)
O13—Mo2—O9	73.51 (5)	C7—C6—H6	119.3
O10—Mo2—O6ⁱ	168.92 (7)	C5—C6—H6	119.3
O11—Mo2—O6ⁱ	74.21 (6)	C2—N1—C1	108.3 (3)
O12—Mo2—O6ⁱ	86.40 (6)	C2—N1—H1N	123 (3)
O13—Mo2—O6ⁱ	81.67 (5)	C1—N1—H1N	129 (3)
O9—Mo2—O6ⁱ	74.69 (5)	C15—C16—C11	121.6 (3)
O5—Mo4—O4	104.52 (8)	C15—C16—H16	119.2
O5—Mo4—O12ⁱⁱ	97.79 (7)	C11—C16—H16	119.2
O4—Mo4—O12ⁱⁱ	102.02 (7)	N1—C2—N2	108.6 (3)
O5—Mo4—O3	97.31 (7)	N1—C2—H2	125.7
O4—Mo4—O3	96.05 (7)	N2—C2—H2	125.7
O12ⁱⁱ—Mo4—O3	152.67 (6)	N2—C4—C5	112.3 (2)
O5—Mo4—O6	100.12 (7)	N2—C4—H4A	109.2
O4—Mo4—O6	154.02 (7)	C5—C4—H4A	109.2
O12ⁱⁱ—Mo4—O6	82.45 (6)	N2—C4—H4B	109.2
O3—Mo4—O6	72.55 (5)	C5—C4—H4B	109.2
O5—Mo4—O11ⁱ	170.62 (7)	H4A—C4—H4B	107.9
O4—Mo4—O11ⁱ	84.82 (7)	C16—C15—C14	120.2 (3)
O12ⁱⁱ—Mo4—O11ⁱ	80.80 (6)	C16—C15—H15	119.9
O3—Mo4—O11ⁱ	80.61 (5)	C14—C15—H15	119.9
O6—Mo4—O11ⁱ	70.51 (5)	C18—N4—C19	109.3 (2)
C7—C8—C9	117.6 (2)	C18—N4—H4N	125.6 (17)
C7—C8—C11	120.9 (2)	C19—N4—H4N	125.0 (17)
C9—C8—C11	121.5 (2)	C1—C3—N2	107.4 (3)
Mo2—O11—Mo4ⁱ	116.73 (7)	C1—C3—H3	126.3
Mo3—O8—Mo1ⁱ	117.38 (7)	N2—C3—H3	126.3
C13—C14—C15	118.4 (3)	C6—C5—C10	117.6 (3)
C13—C14—C17	120.7 (3)	C6—C5—C4	121.1 (2)
C15—C14—C17	120.9 (3)	C10—C5—C4	121.3 (2)
Mo3—O9—Mo2	146.85 (7)	C12—C13—C14	121.3 (3)
Mo3—O9—Mo1	102.58 (5)	C12—C13—H13	119.4
Mo2—O9—Mo1	96.79 (5)	C14—C13—H13	119.4
Mo3—O9—Mo3ⁱ	104.62 (5)	C10—C9—C8	121.2 (2)
Mo2—O9—Mo3ⁱ	99.61 (5)	C10—C9—H9	119.4
Mo1—O9—Mo3ⁱ	96.33 (5)	C8—C9—H9	119.4
C6—C7—C8	121.1 (3)	C3—C1—N1	107.4 (4)
C6—C7—H7	119.5	C3—C1—H1	126.3
C8—C7—H7	119.5	N1—C1—H1	126.3

O10—Mo2—O11—Mo4ⁱ	178.62 (8)	O10—Mo2—O12—Mo4ⁱⁱⁱ	−5.7 (3)
O12—Mo2—O11—Mo4ⁱ	−74.14 (8)	O11—Mo2—O12—Mo4ⁱⁱⁱ	−110.1 (3)
O13—Mo2—O11—Mo4ⁱ	29.20 (17)	O13—Mo2—O12—Mo4ⁱⁱⁱ	94.9 (3)
O9—Mo2—O11—Mo4ⁱ	82.32 (7)	O9—Mo2—O12—Mo4ⁱⁱⁱ	132.1 (3)
O6ⁱ—Mo2—O11—Mo4ⁱ	8.70 (5)	O6ⁱ—Mo2—O12—Mo4ⁱⁱⁱ	176.9 (3)
O7—Mo3—O8—Mo1ⁱ	179.62 (7)	O1—Mo1—O13—Mo2	−170.08 (8)
O6—Mo3—O8—Mo1ⁱ	70.66 (8)	O2—Mo1—O13—Mo2	81.34 (8)
O9—Mo3—O8—Mo1ⁱ	−75.66 (7)	O3—Mo1—O13—Mo2	−32.19 (13)
O3—Mo3—O8—Mo1ⁱ	−7.98 (18)	O9—Mo1—O13—Mo2	−18.61 (6)
O9ⁱ—Mo3—O8—Mo1ⁱ	−2.85 (6)	O8ⁱ—Mo1—O13—Mo2	−90.29 (7)
O7—Mo3—O9—Mo2	45.50 (14)	O10—Mo2—O13—Mo1	−72.56 (9)
O8—Mo3—O9—Mo2	−61.79 (14)	O11—Mo2—O13—Mo1	76.76 (15)
O6—Mo3—O9—Mo2	178.76 (10)	O12—Mo2—O13—Mo1	−176.27 (8)
O3—Mo3—O9—Mo2	141.41 (14)	O9—Mo2—O13—Mo1	20.25 (6)
O9ⁱ—Mo3—O9—Mo2	−135.65 (16)	O6ⁱ—Mo2—O13—Mo1	96.67 (7)
O7—Mo3—O9—Mo1	−78.78 (7)	O1—Mo1—O3—Mo4	−41.21 (16)
O8—Mo3—O9—Mo1	173.93 (6)	O2—Mo1—O3—Mo4	66.75 (15)
O6—Mo3—O9—Mo1	54.48 (11)	O13—Mo1—O3—Mo4	−178.65 (11)
O3—Mo3—O9—Mo1	17.13 (5)	O9—Mo1—O3—Mo4	167.74 (16)
O9ⁱ—Mo3—O9—Mo1	100.07 (6)	O8ⁱ—Mo1—O3—Mo4	−120.42 (15)
O7—Mo3—O9—Mo3ⁱ	−178.85 (6)	O1—Mo1—O3—Mo3	168.78 (7)
O8—Mo3—O9—Mo3ⁱ	73.85 (6)	O2—Mo1—O3—Mo3	−83.27 (8)
O6—Mo3—O9—Mo3ⁱ	−45.59 (11)	O13—Mo1—O3—Mo3	31.33 (12)
O3—Mo3—O9—Mo3ⁱ	−82.95 (6)	O9—Mo1—O3—Mo3	17.72 (5)
O9ⁱ—Mo3—O9—Mo3ⁱ	0.0	O8ⁱ—Mo1—O3—Mo3	89.56 (6)
O10—Mo2—O9—Mo3	−40.83 (14)	O5—Mo4—O3—Mo1	−68.50 (15)
O11—Mo2—O9—Mo3	60.04 (13)	O4—Mo4—O3—Mo1	37.03 (15)
O12—Mo2—O9—Mo3	179.98 (11)	O12ⁱⁱ—Mo4—O3—Mo1	168.42 (12)
O13—Mo2—O9—Mo3	−141.13 (14)	O6—Mo4—O3—Mo1	−166.86 (15)
O6ⁱ—Mo2—O9—Mo3	133.21 (14)	O11ⁱ—Mo4—O3—Mo1	120.74 (15)
O10—Mo2—O9—Mo1	84.87 (7)	O5—Mo4—O3—Mo3	82.27 (8)
O11—Mo2—O9—Mo1	−174.26 (6)	O4—Mo4—O3—Mo3	−172.19 (7)
O12—Mo2—O9—Mo1	−54.32 (15)	O12ⁱⁱ—Mo4—O3—Mo3	−40.81 (17)
O13—Mo2—O9—Mo1	−15.43 (5)	O6—Mo4—O3—Mo3	−16.09 (5)
O6ⁱ—Mo2—O9—Mo1	−101.10 (6)	O11ⁱ—Mo4—O3—Mo3	−88.48 (6)
O10—Mo2—O9—Mo3ⁱ	−177.51 (7)	O7—Mo3—O3—Mo1	79.61 (7)
O11—Mo2—O9—Mo3ⁱ	−76.64 (6)	O8—Mo3—O3—Mo1	−92.96 (14)
O12—Mo2—O9—Mo3ⁱ	43.30 (15)	O6—Mo3—O3—Mo1	−177.22 (7)
O13—Mo2—O9—Mo3ⁱ	82.19 (6)	O9—Mo3—O3—Mo1	−20.31 (6)
O6ⁱ—Mo2—O9—Mo3ⁱ	−3.47 (4)	O9ⁱ—Mo3—O3—Mo1	−98.04 (6)
O1—Mo1—O9—Mo3	−106.35 (13)	O7—Mo3—O3—Mo4	−84.57 (7)
O2—Mo1—O9—Mo3	73.42 (7)	O8—Mo3—O3—Mo4	102.86 (14)
O13—Mo1—O9—Mo3	169.71 (7)	O6—Mo3—O3—Mo4	18.60 (6)
O3—Mo1—O9—Mo3	−19.15 (6)	O9—Mo3—O3—Mo4	175.51 (7)
O8ⁱ—Mo1—O9—Mo3	−104.55 (6)	O9ⁱ—Mo3—O3—Mo4	97.78 (6)
O1—Mo1—O9—Mo2	100.72 (13)	C16—C11—C12—C13	−0.1 (4)
O2—Mo1—O9—Mo2	−79.51 (7)	C8—C11—C12—C13	−179.6 (2)
O13—Mo1—O9—Mo2	16.78 (5)	N4—C18—N3—C20	−0.6 (3)
O3—Mo1—O9—Mo2	−172.08 (7)	N4—C18—N3—C17	−176.1 (2)
O8ⁱ—Mo1—O9—Mo2	102.52 (6)	C14—C17—N3—C18	101.9 (3)
O1—Mo1—O9—Mo3ⁱ	0.21 (15)	C14—C17—N3—C20	−72.8 (4)
O2—Mo1—O9—Mo3ⁱ	179.98 (6)	N4—C19—C20—N3	−0.1 (3)
O13—Mo1—O9—Mo3ⁱ	−83.73 (6)	C18—N3—C20—C19	0.4 (3)
O3—Mo1—O9—Mo3ⁱ	87.41 (5)	C17—N3—C20—C19	175.7 (3)
O8ⁱ—Mo1—O9—Mo3ⁱ	2.01 (4)	C8—C7—C6—C5	0.6 (5)
C9—C8—C7—C6	−0.1 (4)	C12—C11—C16—C15	−0.1 (4)
C11—C8—C7—C6	178.2 (3)	C8—C11—C16—C15	179.4 (3)
C13—C14—C17—N3	108.2 (3)	C1—N1—C2—N2	0.6 (4)
C15—C14—C17—N3	−72.2 (4)	C3—N2—C2—N1	−0.7 (3)
O7—Mo3—O6—Mo4	78.17 (8)	C4—N2—C2—N1	179.3 (2)
O8—Mo3—O6—Mo4	−172.77 (6)	C2—N2—C4—C5	−78.1 (3)
O9—Mo3—O6—Mo4	−54.32 (11)	C3—N2—C4—C5	101.9 (3)
O3—Mo3—O6—Mo4	−17.26 (5)	C11—C16—C15—C14	0.3 (5)
O9ⁱ—Mo3—O6—Mo4	−99.52 (6)	C13—C14—C15—C16	−0.3 (4)
O7—Mo3—O6—Mo2ⁱ	−178.32 (7)	C17—C14—C15—C16	−180.0 (3)
O8—Mo3—O6—Mo2ⁱ	−69.27 (7)	N3—C18—N4—C19	0.6 (3)
O9—Mo3—O6—Mo2ⁱ	49.18 (12)	C20—C19—N4—C18	−0.3 (3)
O3—Mo3—O6—Mo2ⁱ	86.24 (6)	C2—N2—C3—C1	0.5 (4)
O9ⁱ—Mo3—O6—Mo2ⁱ	3.98 (5)	C4—N2—C3—C1	−179.4 (3)
O5—Mo4—O6—Mo3	−75.45 (8)	C7—C6—C5—C10	−0.4 (5)
O4—Mo4—O6—Mo3	85.95 (15)	C7—C6—C5—C4	179.3 (3)
O12ⁱⁱ—Mo4—O6—Mo3	−172.07 (8)	C9—C10—C5—C6	−0.4 (4)
O3—Mo4—O6—Mo3	19.10 (6)	C9—C10—C5—C4	179.9 (3)
O11ⁱ—Mo4—O6—Mo3	105.07 (7)	N2—C4—C5—C6	108.8 (3)
O5—Mo4—O6—Mo2ⁱ	173.01 (6)	N2—C4—C5—C10	−71.5 (3)
O4—Mo4—O6—Mo2ⁱ	−25.59 (16)	C11—C12—C13—C14	0.0 (4)
O12ⁱⁱ—Mo4—O6—Mo2ⁱ	76.39 (6)	C15—C14—C13—C12	0.2 (4)
O3—Mo4—O6—Mo2ⁱ	−92.44 (6)	C17—C14—C13—C12	179.9 (2)
O11ⁱ—Mo4—O6—Mo2ⁱ	−6.47 (4)	C5—C10—C9—C8	0.9 (4)
C7—C8—C11—C12	−31.8 (4)	C7—C8—C9—C10	−0.7 (4)
C9—C8—C11—C12	146.5 (3)	C11—C8—C9—C10	−179.0 (2)
C7—C8—C11—C16	148.8 (3)	N2—C3—C1—N1	−0.1 (4)
C9—C8—C11—C16	−32.9 (4)	C2—N1—C1—C3	−0.3 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O4^iv	0.92 (3)	1.96 (3)	2.854 (4)	165 (3)
N4—H4N···O13^v	0.92 (3)	1.77 (2)	2.658 (3)	163 (3)

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

Experimental details

Crystal data
Chemical formula	(C₂₀H₂₀N₄)₂[Mo₈O₂₆]
M_r	1816.32
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	9.6460 (4), 17.3370 (6), 16.6620 (6)
β (°)	106.145 (1)
V (Å³)	2676.54 (17)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.90
Crystal size (mm)	0.28 × 0.27 × 0.23

Data collection
Diffractometer	Bruker APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.559, 0.616
No. of measured, independent and observed [I > 2σ(I)] reflections	16209, 6405, 5716
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.021, 0.051, 1.03
No. of reflections	6405
No. of parameters	378
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.01, −0.57

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Crystal Impact, 2008).

Selected bond lengths (Å) top

Mo3—O7	1.6929 (15)	Mo2—O10	1.6858 (15)
Mo3—O8	1.7365 (14)	Mo2—O11	1.7665 (15)
Mo3—O6	1.8705 (13)	Mo2—O12	1.8428 (14)
Mo3—O9	1.9774 (13)	Mo2—O13	2.0340 (14)
Mo3—O3	2.1723 (14)	Mo2—O9	2.0869 (12)
Mo3—O9ⁱ	2.4785 (13)	Mo2—O6ⁱ	2.4210 (14)
Mo1—O1	1.6958 (16)	Mo4—O5	1.6870 (16)
Mo1—O2	1.6996 (15)	Mo4—O4	1.7163 (16)
Mo1—O13	1.8952 (13)	Mo4—O12ⁱⁱ	1.9289 (14)
Mo1—O3	1.9789 (13)	Mo4—O3	1.9958 (13)
Mo1—O9	2.2882 (14)	Mo4—O6	2.1806 (14)
Mo1—O8ⁱ	2.4032 (14)	Mo4—O11ⁱ	2.2857 (15)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O4ⁱⁱⁱ	0.92 (3)	1.96 (3)	2.854 (4)	165 (3)
N4—H4N···O13^iv	0.92 (3)	1.77 (2)	2.658 (3)	163 (3)

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

References

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Volume 66| Part 4| April 2010| Pages m443-m444

doi:10.1107/S1600536810010111

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

Poly[bis­­{3,3′-[(bi­phenyl-4,4′-di­yl)di­methyl­ene]diimidazol-1-ium} γ-octa­molybdate(VI)]

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Experimental

Crystal data

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Refinement

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metal-organic compounds

Poly[bis{3,3′-[(biphenyl-4,4′-diyl)dimethylene]diimidazol-1-ium} γ-octamolybdate(VI)]