Poly[[μ2-1,4-bis­(imidazol-1-ylmethyl)­benzene](μ4-3,5,9,11-tetra­oxo-4,10-diaza­tetra­cyclo­[5.5.2.02,6.08,12]tetra­dec-13-ene-4,10-diido)disilver(I)]

Zhang, Y.

doi:10.1107/S1600536812039669

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 10| October 2012| Pages m1289-m1290

https://doi.org/10.1107/S1600536812039669

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Poly[[μ₂-1,4-bis(imidazol-1-ylmethyl)benzene](μ₄-3,5,9,11-tetraoxo-4,10-diazatetracyclo[5.5.2.0^2,6.0^8,12]tetradec-13-ene-4,10-diido)disilver(I)]

Yongmei Zhang ^a ^*

^aSchool of Chemistry and Life Science, Anshan Normal University, Anshan, Liaoning 114000, People's Republic of China
^*Correspondence e-mail: chemzhangym@163.com

(Received 4 September 2012; accepted 18 September 2012; online 22 September 2012)

In the title complex, [Ag₂(C₁₂H₈N₂O₄)(C₁₄H₁₄N₄)]_n, one Ag^I ion, lying on a twofold rotation axis, is coordinated by two N atoms from two 3,5,9,11-tetraoxo-4,10-diazatetracyclo[5.5.2.0^2,6.0^8,12]tetradec-13-ene-4,10-diide (L) ligands in a nearly linear arrangement. The other Ag^I ion, lying on an inversion center, is coordinated by two O atoms from two L ligands and two N atoms from two 1,4-bis(imidazol-1-ylmethyl)benzene ligands in a distorted square-planar geometry. An additional Ag⋯Ag [3.0119 (3) Å] interaction links the Ag^I ions into a chain along [010]. The two types of ligands have mirror symmetry and connect the Ag^I ions into a layer parallel to (100).

Related literature

For the design and synthesis of coordination polymers, see: Liao et al. (2008 ); Song et al. (2012 ); Wang et al. (2009 ). For the van der Waals radius of the Ag atom, see: Bondi (1964 ).

Experimental

Crystal data

[Ag₂(C₁₂H₈N₂O₄)(C₁₄H₁₄N₄)]
M_r = 698.24
Orthorhombic, P b c m
a = 10.1480 (11) Å
b = 11.0016 (11) Å
c = 21.183 (2) Å
V = 2365.0 (4) Å³
Z = 4
Mo Kα radiation
μ = 1.71 mm⁻¹
T = 296 K
0.27 × 0.21 × 0.17 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.656, T_max = 0.760
12177 measured reflections
2402 independent reflections
1454 reflections with I > 2σ(I)
R_int = 0.056

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.094
S = 1.00
2402 reflections
180 parameters
H-atom parameters constrained
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.59 e Å⁻³

Table 1
Selected bond lengths (Å)

Ag1—N1	2.078 (4)
Ag2—N2	2.141 (4)
Ag2—O2	2.693 (3)

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999 ); software used to prepare material for publication: SHELXTL .

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812039669/ng5293sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812039669/ng5293Isup2.hkl

checkCIF report

Comment top

Metal-organic frameworks (MOFs) are an emerging class of periodic crystalline solid-state materials constructed from metal ions or polynuclear metal-oxygen clusters and multidentate organic ligands. Recently, chemists have devoted themselves to the design and syntheses of coordination polymers, not only owing to their potential applications in the realm of gas adsorption and separation, catalysis, magnetism, luminescence and host–guest chemistry and etc, but also for their aesthetic and often complicated architectures and topologies (Liao et al., 2008; Song et al., 2012; Wang et al., 2009). Bicyclo[2.2.2]oct-7-ene-2,3,5,6-tetracarboxydiimide (H₂L), prepared by the ammonolysis of bicyclo[2.2.2]oct-7-ene-2,3,5,6-tetracarboxylic dianhydride, contains two kinds of possible coordination donors (N and O) to ligate metal atoms. Herein, we report a coordination polymer by simultaneous use of the H₂L ligand and a neutral ligand, 1,4-bis(imidazol-l-ylmethyl)benzene.

As shown in Fig. 1 and Table 1, the title complex contains two crystallographically unique Ag^I ions. The Ag1 atom, lying on a twofold rotation axis, is coordinated by two N atoms from two 3,5,9,11-tetraoxo-4,10-diazatetracyclo [5.5.2.0^2,6.0^8,12]tetradec-13-ene-4,10-diido (L₁) ligands in a nearly linear arrangement. The Ag2 atom, lying on an inversion center, is coordinated by two O atoms from two L₁ ligands and two N atoms from two 1,4-bis(imidazol-1-ylmethyl)benzene (L₂) ligands in a distorted square-planar geometry. The Ag···Ag separation [3.0119 (3) Å] is shorter than the sum of van der Waals radii for two silver atoms (3.44 Å) (Bondi, 1964), which indicates relatively strong argentophilicity. The L₁ and L₂ ligands, both have a mirror symmetry, connect the Ag^I ions into a layer structure parallel to (1 0 0) (Fig. 2).

Related literature top

For the design and synthesis of coordination polymers, see: Liao et al. (2008); Song et al. (2012); Wang et al. (2009). For the van der Waals radius of the Ag atom, see: Bondi (1964).

Experimental top

A mixture of bicyclo[2,2,2]oct-7-ene-2,3,5,6-tetracarboxylic dianhydride (0.2 mmol, 0.050 g), 1,4-bis(imidazol-l-ylmethyl)benzene (0.2 mmol, 0.048 g), silver nitrate (0.4 mmol, 0.068 g) and H₂O (25 ml) was stirred for ten minutes. Dilute ammonia was dropwised into the mixture until the mixture turned to transparent. Colorless block crystals of the title compound were isolated after evaporation of ammonia.

Structure description top

For the design and synthesis of coordination polymers, see: Liao et al. (2008); Song et al. (2012); Wang et al. (2009). For the van der Waals radius of the Ag atom, see: Bondi (1964).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 30% probability level. [Symmetry codes: (i) x, y, 1/2 - z; (ii) x, y, 3/2 - z; (iii) -x, -y, 1 - z.]
	Fig. 2. View of the layer structure of the title compound.

Poly[[µ₂-1,4-bis(imidazol-1-ylmethyl)benzene](µ₄-3,5,9,11-tetraoxo- 4,10-diazatetracyclo[5.5.2.0^2,6.0^8,12]tetradec-13-ene-4,10- diido)disilver(I)] top

Crystal data top

[Ag₂(C₁₂H₈N₂O₄)(C₁₄H₁₄N₄)]	F(000) = 1384
M_r = 698.24	D_x = 1.961 Mg m⁻³
Orthorhombic, Pbcm	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2c 2b	Cell parameters from 3256 reflections
a = 10.1480 (11) Å	θ = 2.8–25.9°
b = 11.0016 (11) Å	µ = 1.71 mm⁻¹
c = 21.183 (2) Å	T = 296 K
V = 2365.0 (4) Å³	Block, colorless
Z = 4	0.27 × 0.21 × 0.17 mm

Data collection top

Bruker APEXII CCD diffractometer	2402 independent reflections
Radiation source: fine-focus sealed tube	1454 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.056
φ and ω scans	θ_max = 26.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −12→12
T_min = 0.656, T_max = 0.760	k = −6→13
12177 measured reflections	l = −26→24

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) = 0.094	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0389P)² + 3.7137P] where P = (F_o² + 2F_c²)/3
2402 reflections	(Δ/σ)_max < 0.001
180 parameters	Δρ_max = 0.58 e Å⁻³
0 restraints	Δρ_min = −0.59 e Å⁻³

Crystal data top

[Ag₂(C₁₂H₈N₂O₄)(C₁₄H₁₄N₄)]	V = 2365.0 (4) Å³
M_r = 698.24	Z = 4
Orthorhombic, Pbcm	Mo Kα radiation
a = 10.1480 (11) Å	µ = 1.71 mm⁻¹
b = 11.0016 (11) Å	T = 296 K
c = 21.183 (2) Å	0.27 × 0.21 × 0.17 mm

Data collection top

Bruker APEXII CCD diffractometer	2402 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1454 reflections with I > 2σ(I)
T_min = 0.656, T_max = 0.760	R_int = 0.056
12177 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.094	H-atom parameters constrained
S = 1.00	Δρ_max = 0.58 e Å⁻³
2402 reflections	Δρ_min = −0.59 e Å⁻³
180 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
C1	−0.2448 (5)	0.2484 (5)	0.3711 (2)	0.0310 (10)
C2	−0.2537 (5)	0.1795 (4)	0.3080 (2)	0.0280 (11)
H2	−0.3320	0.1274	0.3076	0.034*
C3	−0.2545 (7)	0.2650 (6)	0.2500	0.0272 (16)
H3	−0.3315	0.3188	0.2500	0.033*
C4	−0.1301 (8)	0.3340 (7)	0.2500	0.0347 (18)
H4	−0.1280	0.4185	0.2500	0.042*
C5	−0.0208 (7)	0.2669 (7)	0.2500	0.0340 (19)
H5	0.0633	0.3006	0.2500	0.041*
C6	−0.0445 (7)	0.1334 (7)	0.2500	0.0281 (17)
H6	0.0385	0.0879	0.2500	0.034*
C7	−0.1291 (5)	0.1015 (4)	0.3074 (2)	0.0272 (11)
H7	−0.1521	0.0150	0.3070	0.033*
C8	−0.0604 (5)	0.1346 (5)	0.3690 (2)	0.0301 (12)
C9	0.1964 (5)	0.1716 (5)	0.5666 (2)	0.0318 (13)
H9	0.1268	0.2226	0.5772	0.038*
C10	0.3079 (5)	0.0219 (5)	0.5312 (3)	0.0331 (13)
H10	0.3296	−0.0512	0.5118	0.040*
C11	0.3947 (5)	0.0980 (5)	0.5586 (3)	0.0352 (13)
H11	0.4853	0.0874	0.5619	0.042*
C12	0.3719 (5)	0.3029 (5)	0.6131 (2)	0.0289 (11)
H12A	0.3208	0.3726	0.5994	0.035*
H12B	0.4625	0.3164	0.6003	0.035*
C13	0.3669 (4)	0.2965 (4)	0.6840 (2)	0.0236 (10)
C14	0.3774 (5)	0.1894 (5)	0.7176 (2)	0.0308 (12)
H14	0.3845	0.1161	0.6960	0.037*
C15	0.3563 (5)	0.4041 (4)	0.7176 (2)	0.0308 (12)
H15	0.3490	0.4774	0.6959	0.037*
N1	−0.1358 (4)	0.2134 (4)	0.40402 (18)	0.0290 (10)
N2	0.1828 (4)	0.0679 (4)	0.53608 (19)	0.0276 (10)
N3	0.3223 (4)	0.1942 (4)	0.58061 (18)	0.0267 (9)
O1	−0.3267 (4)	0.3211 (4)	0.38995 (17)	0.0445 (10)
O2	0.0466 (3)	0.0946 (3)	0.38487 (16)	0.0346 (9)
Ag1	−0.12096 (5)	0.2500	0.5000	0.02695 (15)
Ag2	0.0000	0.0000	0.5000	0.03030 (16)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.030 (2)	0.043 (3)	0.020 (2)	−0.001 (3)	0.005 (2)	−0.005 (3)
C2	0.028 (3)	0.030 (3)	0.026 (3)	−0.005 (2)	−0.001 (2)	0.000 (2)
C3	0.029 (4)	0.038 (5)	0.015 (3)	0.014 (4)	0.000	0.000
C4	0.042 (5)	0.027 (4)	0.036 (5)	−0.005 (4)	0.000	0.000
C5	0.030 (4)	0.046 (6)	0.026 (4)	−0.006 (4)	0.000	0.000
C6	0.030 (4)	0.038 (5)	0.017 (4)	0.008 (4)	0.000	0.000
C7	0.035 (3)	0.022 (3)	0.024 (3)	0.000 (2)	−0.001 (2)	0.000 (2)
C8	0.040 (3)	0.035 (3)	0.015 (3)	0.000 (3)	0.001 (2)	0.006 (2)
C9	0.030 (3)	0.035 (3)	0.031 (3)	0.002 (2)	−0.010 (2)	0.001 (2)
C10	0.033 (3)	0.035 (3)	0.032 (3)	−0.005 (2)	0.003 (2)	−0.007 (2)
C11	0.020 (3)	0.044 (3)	0.042 (3)	−0.004 (2)	0.000 (2)	−0.008 (3)
C12	0.033 (3)	0.029 (3)	0.024 (3)	−0.008 (2)	−0.008 (2)	0.001 (2)
C13	0.018 (2)	0.029 (3)	0.024 (2)	−0.002 (2)	−0.003 (2)	0.000 (2)
C14	0.038 (3)	0.023 (3)	0.031 (3)	−0.002 (2)	0.004 (2)	−0.011 (2)
C15	0.041 (3)	0.022 (3)	0.029 (3)	0.004 (2)	0.000 (2)	0.003 (2)
N1	0.032 (2)	0.040 (3)	0.015 (2)	0.0025 (19)	0.0010 (18)	−0.0032 (17)
N2	0.031 (2)	0.029 (2)	0.022 (2)	−0.0052 (19)	−0.0065 (18)	0.0016 (19)
N3	0.030 (2)	0.029 (2)	0.020 (2)	−0.0038 (19)	−0.0018 (19)	−0.0005 (19)
O1	0.036 (2)	0.065 (3)	0.033 (2)	0.016 (2)	0.0056 (18)	−0.014 (2)
O2	0.033 (2)	0.047 (2)	0.0235 (19)	0.0068 (18)	−0.0057 (16)	0.0033 (17)
Ag1	0.0308 (3)	0.0334 (3)	0.0167 (3)	0.000	0.000	−0.0039 (2)
Ag2	0.0293 (3)	0.0300 (3)	0.0316 (3)	−0.0038 (2)	−0.0104 (3)	0.0022 (3)

Geometric parameters (Å, º) top

C1—O1	1.221 (6)	C9—N3	1.334 (6)
C1—N1	1.363 (6)	C9—H9	0.9300
C1—C2	1.538 (6)	C10—C11	1.347 (7)
C2—C7	1.527 (7)	C10—N2	1.370 (6)
C2—C3	1.548 (6)	C10—H10	0.9300
C2—H2	0.9800	C11—N3	1.370 (6)
C3—C4	1.473 (10)	C11—H11	0.9300
C3—C2ⁱ	1.548 (6)	C12—N3	1.469 (6)
C3—H3	0.9800	C12—C13	1.505 (6)
C4—C5	1.333 (10)	C12—H12A	0.9700
C4—H4	0.9300	C12—H12B	0.9700
C5—C6	1.487 (9)	C13—C14	1.381 (7)
C5—H5	0.9300	C13—C15	1.385 (7)
C6—C7ⁱ	1.530 (6)	C14—C14ⁱⁱ	1.372 (10)
C6—C7	1.530 (6)	C14—H14	0.9300
C6—H6	0.9800	C15—C15ⁱⁱ	1.373 (10)
C7—C8	1.524 (7)	C15—H15	0.9300
C7—H7	0.9800	Ag1—N1	2.078 (4)
C8—O2	1.218 (6)	Ag2—N2	2.141 (4)
C8—N1	1.374 (6)	Ag2—O2	2.693 (3)
C9—N2	1.319 (6)	Ag1—Ag2	3.0119 (3)

O1—C1—N1	124.7 (4)	N2—C10—H10	124.9
O1—C1—C2	124.5 (5)	C10—C11—N3	106.0 (5)
N1—C1—C2	110.7 (4)	C10—C11—H11	127.0
C7—C2—C1	103.6 (4)	N3—C11—H11	127.0
C7—C2—C3	109.8 (4)	N3—C12—C13	114.7 (4)
C1—C2—C3	113.0 (4)	N3—C12—H12A	108.6
C7—C2—H2	110.1	C13—C12—H12A	108.6
C1—C2—H2	110.1	N3—C12—H12B	108.6
C3—C2—H2	110.1	C13—C12—H12B	108.6
C4—C3—C2ⁱ	108.0 (4)	H12A—C12—H12B	107.6
C4—C3—C2	108.0 (4)	C14—C13—C15	118.1 (5)
C2ⁱ—C3—C2	105.1 (5)	C14—C13—C12	123.5 (5)
C4—C3—H3	111.8	C15—C13—C12	118.4 (4)
C2ⁱ—C3—H3	111.8	C14ⁱⁱ—C14—C13	121.0 (3)
C2—C3—H3	111.8	C14ⁱⁱ—C14—H14	119.5
C5—C4—C3	115.3 (7)	C13—C14—H14	119.5
C5—C4—H4	122.3	C15ⁱⁱ—C15—C13	120.9 (3)
C3—C4—H4	122.3	C15ⁱⁱ—C15—H15	119.6
C4—C5—C6	114.3 (7)	C13—C15—H15	119.6
C4—C5—H5	122.8	C1—N1—C8	110.7 (4)
C6—C5—H5	122.8	C1—N1—Ag1	120.4 (3)
C5—C6—C7ⁱ	108.5 (4)	C8—N1—Ag1	127.6 (3)
C5—C6—C7	108.5 (4)	C9—N2—C10	105.0 (4)
C7ⁱ—C6—C7	105.4 (6)	C9—N2—Ag2	124.6 (3)
C5—C6—H6	111.4	C10—N2—Ag2	130.3 (3)
C7ⁱ—C6—H6	111.4	C9—N3—C11	107.1 (4)
C7—C6—H6	111.4	C9—N3—C12	125.8 (4)
C8—C7—C2	103.8 (4)	C11—N3—C12	127.2 (4)
C8—C7—C6	111.7 (4)	N1—Ag1—N1ⁱⁱⁱ	171.7 (2)
C2—C7—C6	110.0 (4)	N1—Ag1—Ag2ⁱⁱⁱ	101.91 (12)
C8—C7—H7	110.4	N1ⁱⁱⁱ—Ag1—Ag2ⁱⁱⁱ	81.53 (11)
C2—C7—H7	110.4	N1—Ag1—Ag2	81.53 (11)
C6—C7—H7	110.4	N1ⁱⁱⁱ—Ag1—Ag2	101.91 (11)
O2—C8—N1	125.1 (5)	Ag2ⁱⁱⁱ—Ag1—Ag2	131.898 (18)
O2—C8—C7	123.9 (5)	N2—Ag2—N2^iv	180.00 (11)
N1—C8—C7	110.9 (4)	N2—Ag2—Ag1^iv	88.01 (11)
N2—C9—N3	111.7 (5)	N2^iv—Ag2—Ag1^iv	91.99 (11)
N2—C9—H9	124.1	N2—Ag2—Ag1	91.99 (11)
N3—C9—H9	124.1	N2^iv—Ag2—Ag1	88.01 (11)
C11—C10—N2	110.1 (5)	N2—Ag2—O2	92.08 (13)
C11—C10—H10	124.9	O2—Ag2—N2^iv	87.92 (13)

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

Experimental details

Crystal data
Chemical formula	[Ag₂(C₁₂H₈N₂O₄)(C₁₄H₁₄N₄)]
M_r	698.24
Crystal system, space group	Orthorhombic, Pbcm
Temperature (K)	296
a, b, c (Å)	10.1480 (11), 11.0016 (11), 21.183 (2)
V (Å³)	2365.0 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.71
Crystal size (mm)	0.27 × 0.21 × 0.17

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.656, 0.760
No. of measured, independent and observed [I > 2σ(I)] reflections	12177, 2402, 1454
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.094, 1.00
No. of reflections	2402
No. of parameters	180
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.58, −0.59

Computer programs: APEX2 (Bruker, 2007), SAINT-Plus (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Ag1—N1	2.078 (4)	Ag2—O2	2.693 (3)
Ag2—N2	2.141 (4)

Acknowledgements

The author thanks Anshan Normal University, Liaoning, China, for supporting this work.

References

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