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Acta Cryst. (2007). E63, m2911    [ doi:10.1107/S1600536807054591 ]

Poly[[[mu]2-1,4-bis(3-pyridylmethoxy)benzene-hemi-[mu]2-fumarato-silver(I)] monohydrate]

S.-L. Li, H.-Y. Bai and J. Yang

Abstract top

The asymmetric unit of the title structure, {[Ag(C18H16N2O2)(C4H2O4)0.5]·H2O}n, contains one AgI cation, one 1,4-bis(3-pyridylmethoxy)benzene (L) ligand, half of a fumarate ligand and one solvent water molecule. The AgI ion is in a distorted tetrahedral coordination geometry. Each L ligand bridges two symmetry-related AgI cations to form extended one-dimensional chains, which are, in turn, bridged by fumarate ligands to create chains of rings. The solvent water molecules donate hydrogen bonds to the carboxylate O atoms of fumarate ligands, generating a two-dimensional supramolecular structure.

Comment top

The design and synthesis of supramolecular complexes exhibiting novel structures and properties has provided exciting new prospects for chemists (Fujita et al., 1995; Yaghi et al., 1995; Zaworotko & Moulton, 2001). Among various supramolecular compounds, Ag(I) compounds are attractive because of their diverse structural types (Corespo et al., 1998). In this paper, we isolated a new Ag supramolecular compound, {[Ag(L)(fum)0.5].H2O}n, constructed using 1,4-bis(pyridin-3-ylmethoxy)benzene (L) and fumarate (fum) ligands.

In the title structure, each AgI cation is four-coordinated and shows a tetrahedral geometry, surrounded by two N atoms from different L ligands and two carboxylate oxygen atoms from different fum anions (Fig. 1). The dihedral angle between two pyridine rings in the same L ligand is 23.6 (5)°. All bond distances and angles are normal (Allen et al., 1987). The L ligands exhibit bis-monodentate coordination modes and links AgI cations to generate an extended chain, which is further linked by fumarate anions to generate a double chainlike structure (Fig. 2). The lattice water molecules donate hydrogen bonds to carboxylate oxygen atoms of fumarate anions from adjacent double-chains, thus forming an intereting two-dimensional supramolecular structure (Fig. 3).

Related literature top

For related literature, see: Allen et al. (1987); Fujita et al. (1995); Yaghi et al. (1995; Zaworotko & Moulton (2001); Corespo et al. (1998).

Experimental top

A mixture of L (0.30 g, 1 mmol), AgNO3 (0.17 g, 1 mmol), fumaric acid (0.12 g, 1 mmol) and H2O (10 ml) was stirred for 1 h and then sealed in a 25 ml Teflonlined stainless steel container. The container was heated to 423 K and held at that temperature for 72 h, then cooled to room temperature at a rate of 10 K h−1. Colorless crystals of the title compound were collected in 56% yield based on Ag.

Refinement top

All H atoms bonded to C atoms were positioned geometrically and refined as riding atoms with C—H = 0.93 A ° and Uiso(H) = 1.2Ueq(C). The water H-atoms were located in a difference Fourier map, and were refined freely with Uiso(H) = 1.5Ueq(O).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top
[Figure 1] Fig. 1. View of the coordination enviroment of an Ag atom. Displacement ellipsoids are drawn at the 30% probability level. Symmetry codes: (i) x + 2, y − 1, z − 1; (ii) 1 − x, −y, 1 − z.
[Figure 2] Fig. 2. Ball-stick representation of part of an extended chain of rings.
[Figure 3] Fig. 3. Ball-stick representation of part of the two-dimensional supramolecular structure. Hydrogen bonds are shown as dashed lines.
Poly[[µ2-1,4-bis(3-pyridylmethoxy)benzene-hemi-µ2-fumarato-silver(I)] hydrate] top
Crystal data top
[Ag(C18H16N2O2)(C4H2O4)0.5]·H2OZ = 2
Mr = 475.24F000 = 480
Triclinic, P1Dx = 1.694 Mg m−3
Hall symbol: -P 1Mo Kα radiation
λ = 0.71069 Å
a = 8.5730 (8) ÅCell parameters from 4127 reflections
b = 9.7120 (9) Åθ = 1.8–28.5º
c = 12.0990 (11) ŵ = 1.12 mm−1
α = 88.845 (2)ºT = 293 (2) K
β = 71.8670 (10)ºBlock, colorless
γ = 77.047 (2)º0.42 × 0.36 × 0.35 mm
V = 931.65 (15) Å3
Data collection top
Bruker APEX CCD area-detector
diffractometer		4127 independent reflections
Radiation source: fine-focus sealed tube3629 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.018
T = 293(2) Kθmax = 28.5º
ω scansθmin = 1.8º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −11→11
Tmin = 0.632, Tmax = 0.676k = −12→12
5611 measured reflectionsl = −15→8
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.107  w = 1/[σ2(Fo2) + (0.0611P)2 + 0.3593P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.001
4127 reflectionsΔρmax = 1.17 e Å−3
259 parametersΔρmin = −0.57 e Å−3
3 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
[Ag(C18H16N2O2)(C4H2O4)0.5]·H2Oγ = 77.047 (2)º
Mr = 475.24V = 931.65 (15) Å3
Triclinic, P1Z = 2
a = 8.5730 (8) ÅMo Kα
b = 9.7120 (9) ŵ = 1.12 mm−1
c = 12.0990 (11) ÅT = 293 (2) K
α = 88.845 (2)º0.42 × 0.36 × 0.35 mm
β = 71.8670 (10)º
Data collection top
Bruker APEX CCD area-detector
diffractometer		4127 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3629 reflections with I > 2σ(I)
Tmin = 0.632, Tmax = 0.676Rint = 0.018
5611 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0343 restraints
wR(F2) = 0.107H atoms treated by a mixture of
independent and constrained refinement
S = 1.09Δρmax = 1.17 e Å−3
4127 reflectionsΔρmin = −0.57 e Å−3
259 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
xyzUiso*/Ueq
Ag10.64106 (3)0.45095 (3)0.55161 (2)0.04642 (11)
C10.4381 (4)0.4066 (3)0.8046 (3)0.0479 (8)
H10.51870.32150.78710.058*
C20.3196 (5)0.4286 (4)0.9124 (3)0.0547 (9)
H20.32240.36130.96800.066*
C30.1954 (4)0.5524 (4)0.9376 (3)0.0476 (7)
H30.11270.56871.01010.057*
C40.1949 (3)0.6511 (3)0.8549 (3)0.0352 (6)
C50.3232 (3)0.6225 (3)0.7493 (3)0.0362 (6)
H50.32620.69020.69370.043*
C60.0622 (4)0.7879 (3)0.8736 (3)0.0391 (6)
H6A0.11430.86820.86400.047*
H6B0.00160.79160.81750.047*
C7−0.1839 (4)0.9076 (3)1.0236 (3)0.0416 (7)
C8−0.2800 (4)0.9094 (3)1.1393 (3)0.0470 (8)
H8−0.25090.83721.18580.056*
C9−0.4204 (4)1.0199 (3)1.1857 (3)0.0448 (7)
H9−0.48611.02091.26310.054*
C10−0.4615 (4)1.1267 (3)1.1173 (3)0.0378 (6)
C11−0.3624 (4)1.1257 (3)1.0023 (3)0.0427 (7)
H11−0.38941.19980.95660.051*
C12−0.2235 (4)1.0157 (3)0.9544 (3)0.0418 (7)
H12−0.15811.01480.87690.050*
C13−0.7012 (4)1.2405 (3)1.2734 (3)0.0409 (7)
H13A−0.63491.24221.32520.049*
H13B−0.74481.15561.28560.049*
C14−0.8441 (3)1.3692 (3)1.2985 (3)0.0354 (6)
C15−0.9936 (3)1.3643 (3)1.3841 (3)0.0356 (6)
H15−1.00211.28011.42080.043*
C16−0.8321 (4)1.4946 (3)1.2444 (3)0.0444 (7)
H16−0.73421.50141.18580.053*
C17−0.9688 (4)1.6107 (4)1.2789 (3)0.0515 (8)
H17−0.96281.69671.24440.062*
C18−1.1126 (4)1.5963 (3)1.3645 (3)0.0457 (7)
H18−1.20371.67401.38700.055*
C190.6094 (4)0.1537 (3)0.5074 (3)0.0428 (7)
C200.5740 (4)0.0108 (3)0.4968 (3)0.0416 (7)
H200.6633−0.06790.48470.050*
N10.4431 (3)0.5020 (3)0.7234 (2)0.0388 (5)
N2−1.1269 (3)1.4750 (3)1.4167 (2)0.0372 (5)
O10.7521 (4)0.1564 (3)0.5123 (4)0.0778 (10)
O20.4997 (3)0.2597 (2)0.5080 (3)0.0596 (7)
O3−0.0494 (3)0.7919 (2)0.9878 (2)0.0562 (7)
O4−0.5989 (3)1.2410 (2)1.15538 (19)0.0470 (5)
O1W1.0451 (6)−0.0306 (5)0.3447 (3)0.0956 (12)
H1A1.107 (6)−0.084 (7)0.378 (5)0.143*
H1B0.946 (3)−0.015 (8)0.392 (5)0.143*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ag10.02882 (14)0.05097 (17)0.04432 (17)−0.00020 (10)0.00425 (10)−0.00846 (11)
C10.0378 (16)0.0375 (15)0.0535 (19)0.0032 (12)−0.0014 (14)−0.0017 (14)
C20.0462 (18)0.0487 (18)0.051 (2)0.0015 (15)0.0014 (15)0.0091 (15)
C30.0387 (16)0.0505 (18)0.0394 (16)−0.0026 (14)0.0027 (13)−0.0011 (13)
C40.0270 (13)0.0354 (14)0.0377 (15)−0.0021 (11)−0.0054 (11)−0.0094 (11)
C50.0308 (13)0.0347 (14)0.0372 (15)−0.0031 (11)−0.0051 (12)−0.0056 (11)
C60.0317 (14)0.0396 (14)0.0357 (15)0.0029 (11)−0.0032 (12)−0.0101 (11)
C70.0293 (14)0.0362 (14)0.0451 (17)0.0034 (11)0.0011 (12)−0.0083 (12)
C80.0381 (16)0.0410 (16)0.0443 (17)0.0069 (13)0.0009 (14)0.0013 (13)
C90.0352 (15)0.0450 (16)0.0370 (16)0.0042 (13)0.0036 (13)−0.0042 (13)
C100.0260 (13)0.0372 (14)0.0393 (15)0.0046 (11)−0.0023 (11)−0.0095 (11)
C110.0346 (15)0.0451 (16)0.0386 (16)0.0049 (12)−0.0072 (13)−0.0017 (13)
C120.0309 (14)0.0505 (17)0.0320 (14)0.0004 (12)0.0010 (12)−0.0076 (12)
C130.0269 (13)0.0400 (15)0.0434 (16)0.0025 (11)−0.0002 (12)−0.0058 (12)
C140.0253 (12)0.0361 (14)0.0371 (15)0.0008 (10)−0.0038 (11)−0.0090 (11)
C150.0259 (13)0.0349 (13)0.0384 (15)−0.0008 (10)−0.0031 (11)−0.0072 (11)
C160.0296 (14)0.0473 (17)0.0466 (17)−0.0040 (12)−0.0017 (13)−0.0006 (13)
C170.0450 (18)0.0400 (16)0.057 (2)−0.0034 (14)−0.0036 (16)0.0044 (14)
C180.0321 (15)0.0407 (16)0.0528 (19)0.0047 (12)−0.0058 (14)−0.0073 (13)
C190.0439 (17)0.0377 (15)0.0421 (17)−0.0125 (13)−0.0046 (13)0.0008 (12)
C200.0426 (16)0.0311 (13)0.0450 (17)−0.0042 (12)−0.0079 (14)0.0014 (12)
N10.0284 (11)0.0365 (12)0.0400 (13)−0.0002 (9)0.0010 (10)−0.0059 (10)
N20.0257 (11)0.0378 (12)0.0397 (13)0.0001 (9)−0.0027 (10)−0.0107 (10)
O10.0632 (18)0.0588 (17)0.124 (3)−0.0218 (14)−0.043 (2)0.0142 (18)
O20.0475 (14)0.0339 (11)0.0852 (19)−0.0040 (10)−0.0071 (13)−0.0046 (11)
O30.0423 (13)0.0443 (12)0.0509 (14)0.0131 (10)0.0132 (11)0.0001 (10)
O40.0330 (11)0.0467 (12)0.0403 (12)0.0127 (9)0.0029 (9)−0.0047 (9)
O1W0.093 (3)0.109 (3)0.073 (2)−0.005 (2)−0.022 (2)0.010 (2)
Geometric parameters (Å, °) top
Ag1—N2i2.202 (2)C10—O41.388 (3)
Ag1—N12.217 (2)C11—C121.386 (4)
Ag1—O22.577 (3)C11—H110.9300
Ag1—Ag1ii3.0193 (5)C12—H120.9300
C1—N11.335 (4)C13—O41.425 (4)
C1—C21.367 (5)C13—C141.501 (4)
C1—H10.9300C13—H13A0.9700
C2—C31.382 (5)C13—H13B0.9700
C2—H20.9300C14—C161.379 (4)
C3—C41.372 (4)C14—C151.384 (4)
C3—H30.9300C15—N21.343 (3)
C4—C51.386 (4)C15—H150.9300
C4—C61.512 (4)C16—C171.393 (4)
C5—N11.341 (4)C16—H160.9300
C5—H50.9300C17—C181.375 (5)
C6—O31.411 (4)C17—H170.9300
C6—H6A0.9700C18—N21.337 (4)
C6—H6B0.9700C18—H180.9300
C7—C121.377 (5)C19—O21.228 (4)
C7—O31.382 (3)C19—O11.250 (4)
C7—C81.384 (4)C19—C201.502 (4)
C8—C91.393 (4)C20—C20iii1.309 (6)
C8—H80.9300C20—H200.9300
C9—C101.366 (4)N2—Ag1iv2.202 (2)
C9—H90.9300O1W—H1A0.85 (6)
C10—C111.386 (4)O1W—H1B0.85 (5)
N2i—Ag1—N1153.76 (10)C10—C11—H11119.6
N2i—Ag1—O2116.46 (9)C7—C12—C11118.9 (3)
N1—Ag1—O289.76 (9)C7—C12—H12120.5
N2i—Ag1—Ag1ii106.01 (7)C11—C12—H12120.5
N1—Ag1—Ag1ii85.94 (7)O4—C13—C14108.2 (2)
O2—Ag1—Ag1ii63.49 (6)O4—C13—H13A110.1
N1—C1—C2122.8 (3)C14—C13—H13A110.1
N1—C1—H1118.6O4—C13—H13B110.1
C2—C1—H1118.6C14—C13—H13B110.1
C1—C2—C3119.0 (3)H13A—C13—H13B108.4
C1—C2—H2120.5C16—C14—C15118.0 (3)
C3—C2—H2120.5C16—C14—C13123.5 (3)
C4—C3—C2119.5 (3)C15—C14—C13118.4 (3)
C4—C3—H3120.2N2—C15—C14123.4 (3)
C2—C3—H3120.2N2—C15—H15118.3
C3—C4—C5117.7 (3)C14—C15—H15118.3
C3—C4—C6123.3 (3)C14—C16—C17119.1 (3)
C5—C4—C6119.0 (3)C14—C16—H16120.5
N1—C5—C4123.3 (3)C17—C16—H16120.5
N1—C5—H5118.4C18—C17—C16119.0 (3)
C4—C5—H5118.4C18—C17—H17120.5
O3—C6—C4107.4 (2)C16—C17—H17120.5
O3—C6—H6A110.2N2—C18—C17122.6 (3)
C4—C6—H6A110.2N2—C18—H18118.7
O3—C6—H6B110.2C17—C18—H18118.7
C4—C6—H6B110.2O2—C19—O1124.1 (3)
H6A—C6—H6B108.5O2—C19—C20118.8 (3)
C12—C7—O3125.2 (3)O1—C19—C20117.1 (3)
C12—C7—C8120.7 (3)C20iii—C20—C19124.6 (4)
O3—C7—C8114.1 (3)C20iii—C20—H20117.7
C7—C8—C9119.7 (3)C19—C20—H20117.7
C7—C8—H8120.1C1—N1—C5117.7 (3)
C9—C8—H8120.1C1—N1—Ag1118.8 (2)
C10—C9—C8120.0 (3)C5—N1—Ag1123.5 (2)
C10—C9—H9120.0C18—N2—C15117.9 (3)
C8—C9—H9120.0C18—N2—Ag1iv122.60 (19)
C9—C10—C11119.9 (3)C15—N2—Ag1iv119.5 (2)
C9—C10—O4124.3 (3)C19—O2—Ag199.6 (2)
C11—C10—O4115.8 (3)C7—O3—C6117.5 (2)
C12—C11—C10120.8 (3)C10—O4—C13115.5 (2)
C12—C11—H11119.6H1A—O1W—H1B106 (6)
N1—C1—C2—C32.4 (6)O1—C19—C20—C20iii172.3 (4)
C1—C2—C3—C4−0.9 (6)C2—C1—N1—C5−1.6 (5)
C2—C3—C4—C5−1.3 (5)C2—C1—N1—Ag1−179.4 (3)
C2—C3—C4—C6178.6 (3)C4—C5—N1—C1−0.8 (5)
C3—C4—C5—N12.2 (5)C4—C5—N1—Ag1176.9 (2)
C6—C4—C5—N1−177.7 (3)N2i—Ag1—N1—C1−109.7 (3)
C3—C4—C6—O31.5 (4)O2—Ag1—N1—C168.1 (3)
C5—C4—C6—O3−178.6 (3)Ag1ii—Ag1—N1—C1131.5 (3)
C12—C7—C8—C91.5 (5)N2i—Ag1—N1—C572.7 (3)
O3—C7—C8—C9−179.3 (3)O2—Ag1—N1—C5−109.5 (2)
C7—C8—C9—C10−0.8 (5)Ag1ii—Ag1—N1—C5−46.1 (2)
C8—C9—C10—C11−0.7 (5)C17—C18—N2—C150.8 (5)
C8—C9—C10—O4179.9 (3)C17—C18—N2—Ag1iv−178.9 (3)
C9—C10—C11—C121.5 (5)C14—C15—N2—C18−0.9 (5)
O4—C10—C11—C12−179.0 (3)C14—C15—N2—Ag1iv178.7 (2)
O3—C7—C12—C11−179.8 (3)O1—C19—O2—Ag1−7.9 (4)
C8—C7—C12—C11−0.7 (5)C20—C19—O2—Ag1173.8 (2)
C10—C11—C12—C7−0.8 (5)N2i—Ag1—O2—C1965.7 (2)
O4—C13—C14—C16−30.1 (4)N1—Ag1—O2—C19−113.2 (2)
O4—C13—C14—C15152.9 (3)Ag1ii—Ag1—O2—C19161.2 (2)
C16—C14—C15—N20.1 (5)C12—C7—O3—C64.0 (5)
C13—C14—C15—N2177.3 (3)C8—C7—O3—C6−175.2 (3)
C15—C14—C16—C170.9 (5)C4—C6—O3—C7−178.9 (3)
C13—C14—C16—C17−176.2 (3)C9—C10—O4—C13−1.1 (5)
C14—C16—C17—C18−1.0 (6)C11—C10—O4—C13179.4 (3)
C16—C17—C18—N20.2 (6)C14—C13—O4—C10−179.0 (3)
O2—C19—C20—C20iii−9.4 (6)
Symmetry codes: (i) x+2, y−1, z−1; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y, −z+1; (iv) x−2, y+1, z+1.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1W—H1B···O10.85 (5)2.23 (5)2.941 (6)141 (7)
O1W—H1A···O1v0.85 (6)2.07 (3)2.888 (5)162 (8)
Symmetry codes: (v) −x+2, −y, −z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1W—H1B···O10.85 (5)2.23 (5)2.941 (6)141 (7)
O1W—H1A···O1i0.85 (6)2.07 (3)2.888 (5)162 (8)
Symmetry codes: (i) −x+2, −y, −z+1.
Acknowledgements top

We thank the Science Foundation for Young Teachers of Northeast Normal University (No. 20060304) for supporting this work.

references
References top

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.

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