Poly[(μ-benzene-1,2,4,5-tetra­carboxyl­ato)tetra­silver(I)]

Tahir, M.N.; Atakol, O.; Tariq, M.I.

doi:10.1107/S1600536809015074

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page m580

doi:10.1107/S1600536809015074

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Poly[(μ-benzene-1,2,4,5-tetracarboxylato)tetrasilver(I)]

M. Nawaz Tahir,^a ^* Orhan Atakol ^b and Muhammad Ilyas Tariq ^c

^aDepartment of Physics, University of Sargodha, Sargodha, Pakistan, ^bDepartment of Chemistry, Faculty of Science, University of Ankara, Ankara, Turkey, and ^cDepartment of Chemistry, University of Sargodha, Sargodha, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 14 February 2009; accepted 22 April 2009; online 30 April 2009)

In the centrosymmetric title compound, [Ag₄(C₁₀H₂O₈)]_n, the benzene ring has irregular bond lengths but remains planar (r.m.s. deviation 0.0002 Å). The Ag—O bond lengths are in the range 2.153 (3)–2.615 (4) Å. The carboxylate groups are oriented at dihedral angles of 26.4 (5) and 74.9 (4)° to the benzene ring. The coordination behaviour of each carboxylate O atom is different: in one carboxylate, the O atoms are coordinated to a single and two Ag atoms; in the other carboxylate, the O atoms are coordinated to two and three Ag atoms. Non-classical intermolecular C—H⋯O hydrogen bonding is present in the crystal structure. The title compound forms a three-dimensional polymeric network due to the coordination of the Ag atoms.

Related literature

For related structures, see: Jaber et al. (1997 ); Tahir et al. (1996 ); Ülkü et al. (1996 ).

Experimental

Crystal data

[Ag₄(C₁₀H₂O₈)]
M_r = 340.80
Monoclinic, P 2₁ /c
a = 8.328 (1) Å
b = 6.317 (1) Å
c = 10.945 (2) Å
β = 94.36 (2)°
V = 574.13 (16) Å³
Z = 4
Mo Kα radiation
μ = 6.76 mm⁻¹
T = 296 K
0.30 × 0.10 × 0.08 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (MolEN; Fair, 1990 ) T_min = 0.448, T_max = 0.578
1680 measured reflections
1308 independent reflections
1268 reflections with I > 2σ(I)
R_int = 0.012
3 standard reflections frequency: 120 min intensity decay: 0.1%

Refinement

R[F² > 2σ(F²)] = 0.026
wR(F²) = 0.089
S = 1.01
1308 reflections
101 parameters
H-atom parameters constrained
Δρ_max = 1.20 e Å⁻³
Δρ_min = −0.79 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O3ⁱ	0.93	2.5400	3.422 (6)	158
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1993 ); cell refinement: CAD-4 EXPRESS; data reduction: MolEN (Fair, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXS97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809015074/rk2131sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809015074/rk2131Isup2.hkl

checkCIF report

Comment top

The crystal structures of poly[bis(p–nitrosalicylato–O:O')disilver(I)] (Tahir et al., 1996) and poly[bis(3,5–dinitrobenzoato–O1:O2) disilver(I)–O2:Ag;Ag':O2'] (Ülkü et al., 1996) have been reported. In continuation to the interest relating to the chemistry of silver coordination with carboxylates, the title compound (I), (Fig. 1) was synthesized.

Crystal structure of silver(I) with 1,2,4,5–benzenetetracarboxylic acid (II) (Jaber et al., 1997) has also been reported. The present complex (I) has been prepared by different method with same ligand as in (II). Due to the change in reaction mechanism, the coordination of O atoms of all carboxylates with Ag atoms has been affected very much. In this centrosymmetric complex, the C–O bond lengths of the carboxylato–groups vary in the range of 1.224 (3) to 1.298 (5) Å. In the benzene ring, the bond lengths of opposite sides are equal having values of 1.359 (6), 1.368 (7) and 1.414 (7) Å. The largest bond is in between the C atoms bearing carboxylate–groups. Although the bond lengths in benzene ring are irregular but it remains planar. In (I), the metallic bond is of 3.0140 (8) Å. The carboxylato–group (O1/C4/O2) makes a dihedral angle of 26.37 (51)° with the benzene ring, while the group (O3/C5/O4) is oriented at 74.90 (37)°. Non–classical intermolecular C2—H2···O3 hydrogen bond was found in the molecular structure. The crystal structure of title compound is stabilized through three dimensional polymeric network.

Related literature top

For related structures, see: Jaber et al. (1997); Tahir et al. (1996); Ülkü et al. (1996).

Experimental top

To the aqueous solution of sodium 1,2,4,5–benzenetetracarboxylate, freshly prepared solution of AgNO₃ was added dropwise with constant stirring until the color was changed. The product was filtered and the filtrate was kept in darkness for the crystallization by slow evaporation. Needle like crystals were obtained after 72 h.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1993); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1993); data reduction: MolEN (Fair, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXS97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. A view of part of polimeric structure of title compound with the atom numbering scheme. Displacement ellipsoids are drawn at 50% probability level. H atom is presented as a small sphere of arbitrary radius. The symmetry codes in labeling are i = -x+1, -y+1, -z+1; ii = -x, -y+1, -z+1; iii = x, -y+1/2, z-1/2; iv = x, -y+3/2, z-1/2; v = -x, y+1/2, -z+1/2; vi = x, -y+1/2, z+1/2; vii = -x, y-1/2, -z+1/2; viii = x, -y+3/2, z+1/2.

Poly[(µ-benzene-1,2,4,5-tetracarboxylato)tetrasilver(I)] top

Crystal data top

[Ag₄(C₁₀H₂O₈)]	F(000) = 628
M_r = 340.80	D_x = 3.943 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 8.328 (1) Å	θ = 11.7–21.0°
b = 6.317 (1) Å	µ = 6.76 mm⁻¹
c = 10.945 (2) Å	T = 296 K
β = 94.36 (2)°	Needle, pale yellow
V = 574.13 (16) Å³	0.30 × 0.10 × 0.08 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.012
ω/2θ scans	θ_max = 28.2°, θ_min = 3.7°
Absorption correction: ψ scan (MolEN; Fair, 1990)	h = 0→10
T_min = 0.448, T_max = 0.578	k = 0→8
1680 measured reflections	l = −14→14
1308 independent reflections	3 standard reflections every 120 min
1268 reflections with I > 2σ(I)	intensity decay: 0.1%

Refinement top

Refinement on F²	Primary atom site location: Patterson
Least-squares matrix: Full	Secondary atom site location: Difmap
R[F² > 2σ(F²)] = 0.026	H-atom parameters constrained
wR(F²) = 0.089	w = 1/[σ²(F_o²) + (0.0599P)² + 3.6455P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
1308 reflections	Δρ_max = 1.20 e Å⁻³
101 parameters	Δρ_min = −0.79 e Å⁻³
0 restraints

Crystal data top

[Ag₄(C₁₀H₂O₈)]	V = 574.13 (16) Å³
M_r = 340.80	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.328 (1) Å	µ = 6.76 mm⁻¹
b = 6.317 (1) Å	T = 296 K
c = 10.945 (2) Å	0.30 × 0.10 × 0.08 mm
β = 94.36 (2)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1268 reflections with I > 2σ(I)
Absorption correction: ψ scan (MolEN; Fair, 1990)	R_int = 0.012
T_min = 0.448, T_max = 0.578	3 standard reflections every 120 min
1680 measured reflections	intensity decay: 0.1%
1308 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	0 restraints
wR(F²) = 0.089	H-atom parameters constrained
S = 1.01	Δρ_max = 1.20 e Å⁻³
1308 reflections	Δρ_min = −0.79 e Å⁻³
101 parameters

Special details top

Experimental. The structure was solved by Patterson method using SHELX86. The whole molecule was recognized.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.s is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Ag1	0.09967 (6)	0.44769 (6)	0.70351 (4)	0.0316 (2)
Ag2	−0.15558 (4)	0.16471 (6)	0.44813 (3)	0.0250 (2)
O1	0.1054 (4)	0.2412 (6)	0.5218 (3)	0.0238 (10)
O2	0.1422 (4)	0.3437 (6)	0.3300 (3)	0.0264 (10)
O3	0.3520 (4)	0.6473 (6)	0.1913 (3)	0.0246 (10)
O4	0.2066 (5)	0.8108 (6)	0.3346 (3)	0.0273 (11)
C1	0.3498 (5)	0.4182 (8)	0.4710 (4)	0.0169 (11)
C2	0.4363 (6)	0.3358 (7)	0.5701 (4)	0.0184 (12)
C3	0.4135 (5)	0.5821 (8)	0.4012 (4)	0.0167 (11)
C4	0.1874 (5)	0.3273 (7)	0.4386 (4)	0.0191 (12)
C5	0.3167 (5)	0.6850 (8)	0.2996 (4)	0.0186 (12)
H2	0.39517	0.22806	0.61643	0.0221*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.0447 (3)	0.0225 (3)	0.0247 (3)	−0.0009 (2)	−0.0155 (2)	−0.0012 (1)
Ag2	0.0254 (3)	0.0282 (3)	0.0195 (3)	−0.0047 (1)	−0.0097 (2)	0.0011 (1)
O1	0.0201 (16)	0.0262 (18)	0.0240 (17)	−0.0079 (13)	−0.0045 (13)	−0.0005 (14)
O2	0.0254 (18)	0.0292 (19)	0.0221 (17)	−0.0027 (14)	−0.0152 (14)	−0.0006 (14)
O3	0.0222 (17)	0.035 (2)	0.0156 (16)	0.0058 (14)	−0.0048 (13)	0.0024 (14)
O4	0.0291 (19)	0.033 (2)	0.0187 (16)	0.0134 (16)	−0.0057 (14)	0.0017 (14)
C1	0.0131 (18)	0.020 (2)	0.0164 (19)	−0.0001 (16)	−0.0070 (15)	0.0001 (16)
C2	0.017 (2)	0.020 (2)	0.017 (2)	−0.0003 (16)	−0.0064 (16)	0.0033 (16)
C3	0.0150 (19)	0.021 (2)	0.0130 (18)	0.0022 (16)	−0.0058 (14)	0.0001 (16)
C4	0.016 (2)	0.016 (2)	0.024 (2)	0.0017 (16)	−0.0059 (17)	−0.0050 (16)
C5	0.015 (2)	0.022 (2)	0.018 (2)	−0.0005 (16)	−0.0046 (16)	0.0013 (16)

Geometric parameters (Å, º) top

Ag1—O1	2.382 (3)	O2—C4	1.224 (5)
Ag1—Ag2ⁱ	3.0140 (8)	O3—C5	1.265 (5)
Ag1—O2ⁱ	2.412 (4)	O4—C5	1.293 (6)
Ag1—O2ⁱⁱ	2.314 (4)	C1—C2	1.359 (6)
Ag1—O4ⁱⁱⁱ	2.233 (4)	C1—C3	1.414 (7)
Ag2—O1	2.311 (3)	C1—C4	1.487 (6)
Ag2—O3^iv	2.153 (3)	C2—C3^vi	1.368 (7)
Ag2—O1^v	2.615 (4)	C3—C5	1.474 (6)
Ag2—O4ⁱ	2.452 (3)	C2—H2	0.9300
O1—C4	1.298 (5)

Ag1···C2	3.334 (5)	O1···O4ⁱ	3.154 (5)
Ag1···C4ⁱ	3.097 (4)	O2···C5	2.635 (6)
Ag1···Ag1^vii	3.7449 (9)	O2···O3	3.072 (5)
Ag1···Ag1^viii	3.7449 (9)	O2···O4	2.999 (5)
Ag1···Ag2^viii	4.0452 (9)	O2···Ag2^xii	3.666 (4)
Ag1···O1^viii	4.022 (4)	O2···Ag2ⁱ	3.939 (4)
Ag1···O1ⁱ	3.495 (4)	O3···O2	3.072 (5)
Ag1···O3ⁱ	4.061 (3)	O3···Ag1ⁱ	4.061 (3)
Ag1···O3ⁱⁱⁱ	3.320 (4)	O4···C4	3.268 (6)
Ag1···C5ⁱ	3.565 (4)	O4···Ag2^xiii	4.026 (4)
Ag1···Ag2ⁱⁱ	3.6134 (9)	O4···O2	2.999 (5)
Ag1···C5ⁱⁱⁱ	3.077 (5)	O4···Ag1ⁱ	3.031 (4)
Ag2···O1ⁱ	3.788 (4)	O4···O1ⁱ	3.155 (5)
Ag2···O4^ix	4.026 (4)	O1···H2	2.5500
Ag2···C2^x	3.898 (5)	O3···H2^xi	2.5400
Ag2···Ag1^vii	4.0452 (9)	C2···Ag1	3.334 (5)
Ag2···C2ⁱ	3.923 (5)	C2···Ag2^xiv	3.898 (5)
Ag2···C1ⁱ	3.250 (5)	C2···Ag2^v	3.928 (5)
Ag2···C2^v	3.928 (5)	C2···Ag2ⁱ	3.923 (5)
Ag2···Ag1^xi	3.6134 (9)	C4···O4	3.268 (6)
Ag2···C4ⁱ	3.458 (4)	C5···O2	2.635 (6)
Ag1···H2	3.0400	C5···Ag1ⁱ	3.565 (4)
Ag2···H2^v	3.2300	H2···Ag1	3.0400
O1···O2	2.240 (5)	H2···O1	2.5500
O1···Ag2ⁱ	3.788 (4)	H2···Ag2^v	3.2300
O1···Ag1^vii	4.022 (4)	H2···O3ⁱⁱ	2.5400
O1···Ag1ⁱ	3.496 (4)

Ag2ⁱ—Ag1—O1	88.36 (9)	Ag2—O1—Ag2^v	88.62 (12)
O1—Ag1—O2ⁱ	103.99 (12)	Ag2^v—O1—C4	114.3 (3)
O1—Ag1—O2ⁱⁱ	92.98 (12)	Ag1ⁱ—O2—C4	112.7 (3)
O1—Ag1—O4ⁱⁱⁱ	151.46 (13)	Ag1^xi—O2—C4	122.4 (3)
Ag2ⁱ—Ag1—O2ⁱ	68.57 (9)	Ag1ⁱ—O2—Ag1^xi	104.81 (13)
Ag2ⁱ—Ag1—O2ⁱⁱ	162.28 (9)	Ag2^xii—O3—C5	115.9 (3)
Ag2ⁱ—Ag1—O4ⁱⁱⁱ	74.22 (9)	Ag2ⁱ—O4—C5	120.3 (3)
O2ⁱ—Ag1—O2ⁱⁱ	127.86 (12)	Ag1^xv—O4—C5	119.1 (3)
O2ⁱ—Ag1—O4ⁱⁱⁱ	90.69 (14)	Ag1^xv—O4—Ag2ⁱ	119.34 (17)
O2ⁱⁱ—Ag1—O4ⁱⁱⁱ	97.10 (13)	C2—C1—C3	120.9 (4)
O1—Ag2—O3^iv	154.36 (13)	C2—C1—C4	117.4 (4)
O1—Ag2—O1^v	91.37 (12)	C3—C1—C4	121.7 (4)
Ag1ⁱ—Ag2—O1	80.89 (9)	C1—C2—C3^vi	117.2 (4)
O1—Ag2—O4ⁱ	82.89 (13)	C1—C3—C5	121.6 (4)
O1^v—Ag2—O3^iv	98.33 (13)	C1—C3—C2^vi	121.8 (4)
Ag1ⁱ—Ag2—O3^iv	78.00 (10)	C2^vi—C3—C5	116.4 (4)
O3^iv—Ag2—O4ⁱ	120.81 (13)	O1—C4—O2	125.3 (4)
Ag1ⁱ—Ag2—O1^v	146.75 (8)	O1—C4—C1	120.8 (4)
O1^v—Ag2—O4ⁱ	88.69 (12)	O2—C4—C1	114.0 (4)
Ag1ⁱ—Ag2—O4ⁱ	121.88 (9)	O3—C5—O4	127.9 (4)
Ag1—O1—Ag2	109.14 (14)	O3—C5—C3	118.1 (4)
Ag1—O1—C4	113.7 (3)	O4—C5—C3	114.0 (4)
Ag1—O1—Ag2^v	116.43 (13)	C1—C2—H2	121.00
Ag2—O1—C4	111.9 (3)	C3^vi—C2—H2	121.00

Ag2ⁱ—Ag1—O1—Ag2	−100.23 (13)	O1—Ag2—O1^v—C4^v	113.6 (3)
Ag2ⁱ—Ag1—O1—C4	25.5 (3)	O1—Ag2—O4ⁱ—C5ⁱ	125.7 (4)
Ag2ⁱ—Ag1—O1—Ag2^v	161.49 (13)	Ag1—O1—C4—O2	−132.9 (4)
O2ⁱ—Ag1—O1—Ag2	−32.80 (17)	Ag1—O1—C4—C1	46.7 (5)
O2ⁱ—Ag1—O1—C4	92.9 (3)	Ag2—O1—C4—O2	−8.7 (6)
O2ⁱ—Ag1—O1—Ag2^v	−131.09 (14)	Ag2—O1—C4—C1	170.9 (3)
O2ⁱⁱ—Ag1—O1—Ag2	97.46 (15)	Ag2^v—O1—C4—O2	90.2 (5)
O2ⁱⁱ—Ag1—O1—C4	−136.8 (3)	Ag2^v—O1—C4—C1	−90.3 (4)
O2ⁱⁱ—Ag1—O1—Ag2^v	−0.82 (15)	Ag1ⁱ—O2—C4—O1	61.0 (5)
O4ⁱⁱⁱ—Ag1—O1—Ag2	−151.8 (2)	Ag1ⁱ—O2—C4—C1	−118.5 (3)
O4ⁱⁱⁱ—Ag1—O1—C4	−26.0 (5)	Ag1^xi—O2—C4—O1	−65.4 (6)
O4ⁱⁱⁱ—Ag1—O1—Ag2^v	110.0 (3)	Ag1^xi—O2—C4—C1	115.1 (4)
O1—Ag1—Ag2ⁱ—O4	−5.35 (14)	Ag2^xii—O3—C5—O4	−31.4 (7)
O1—Ag1—Ag2ⁱ—O1ⁱ	70.34 (12)	Ag2^xii—O3—C5—C3	151.0 (3)
O1—Ag1—Ag2ⁱ—O3ⁱⁱⁱ	−124.33 (13)	Ag2ⁱ—O4—C5—O3	176.4 (4)
O2ⁱ—Ag1—Ag2ⁱ—O4	−111.08 (15)	Ag2ⁱ—O4—C5—C3	−5.9 (5)
O4ⁱⁱⁱ—Ag1—Ag2ⁱ—O4	151.77 (16)	Ag1^xv—O4—C5—O3	−16.2 (7)
O1—Ag1—O2ⁱ—C4ⁱ	−21.4 (3)	Ag1^xv—O4—C5—C3	161.5 (3)
O1—Ag1—O2ⁱⁱ—C4ⁱⁱ	162.7 (3)	C3—C1—C2—C3^vi	−0.1 (7)
O1—Ag1—O4ⁱⁱⁱ—C5ⁱⁱⁱ	17.6 (5)	C4—C1—C2—C3^vi	179.2 (4)
O3^iv—Ag2—O1—Ag1	129.8 (3)	C2—C1—C3—C5	−175.0 (4)
O3^iv—Ag2—O1—C4	3.1 (5)	C2—C1—C3—C2^vi	0.1 (7)
O3^iv—Ag2—O1—Ag2^v	−112.6 (3)	C4—C1—C3—C5	5.7 (7)
O1^v—Ag2—O1—Ag1	−117.55 (14)	C4—C1—C3—C2^vi	−179.2 (4)
O1^v—Ag2—O1—C4	115.8 (3)	C2—C1—C4—O1	27.0 (6)
O1^v—Ag2—O1—Ag2^v	0.03 (10)	C2—C1—C4—O2	−153.5 (4)
Ag1ⁱ—Ag2—O1—Ag1	94.95 (13)	C3—C1—C4—O1	−153.8 (4)
Ag1ⁱ—Ag2—O1—C4	−31.8 (3)	C3—C1—C4—O2	25.8 (6)
Ag1ⁱ—Ag2—O1—Ag2^v	−147.47 (8)	C1—C2—C3^vi—C1^vi	0.1 (7)
O4ⁱ—Ag2—O1—Ag1	−29.04 (15)	C1—C2—C3^vi—C5^vi	−175.3 (4)
O4ⁱ—Ag2—O1—C4	−155.7 (3)	C1—C3—C5—O3	−109.0 (5)
O4ⁱ—Ag2—O1—Ag2^v	88.54 (12)	C1—C3—C5—O4	73.0 (6)
O1—Ag2—O3^iv—C5^iv	8.6 (6)	C2^vi—C3—C5—O3	75.6 (6)
O1—Ag2—O1^v—Ag1^v	−110.74 (15)	C2^vi—C3—C5—O4	−102.3 (5)
O1—Ag2—O1^v—Ag2^v	−0.03 (11)

Symmetry codes: (i) −x, −y+1, −z+1; (ii) x, −y+1/2, z+1/2; (iii) x, −y+3/2, z+1/2; (iv) −x, y−1/2, −z+1/2; (v) −x, −y, −z+1; (vi) −x+1, −y+1, −z+1; (vii) −x, y−1/2, −z+3/2; (viii) −x, y+1/2, −z+3/2; (ix) x, y−1, z; (x) x−1, y, z; (xi) x, −y+1/2, z−1/2; (xii) −x, y+1/2, −z+1/2; (xiii) x, y+1, z; (xiv) x+1, y, z; (xv) x, −y+3/2, z−1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O3ⁱⁱ	0.9300	2.5400	3.422 (6)	158.00

Symmetry code: (ii) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	[Ag₄(C₁₀H₂O₈)]
M_r	340.80
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	8.328 (1), 6.317 (1), 10.945 (2)
β (°)	94.36 (2)
V (Å³)	574.13 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	6.76
Crystal size (mm)	0.30 × 0.10 × 0.08

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (MolEN; Fair, 1990)
T_min, T_max	0.448, 0.578
No. of measured, independent and observed [I > 2σ(I)] reflections	1680, 1308, 1268
R_int	0.012
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.089, 1.01
No. of reflections	1308
No. of parameters	101
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.20, −0.79

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1993), MolEN (Fair, 1990), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O3ⁱ	0.9300	2.5400	3.422 (6)	158.00

Symmetry code: (i) x, −y+1/2, z+1/2.

References

Enraf–Nonius (1993). CAD–4 EXPRESS. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Fair, C. K. (1990). MolEN. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Jaber, F., Charbonnier, F. & Faure, R. (1997). J. Chem. Crystallogr. 27, 397–400. CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tahir, M. N., Ülkü, D. & Muvsumov, E. M. (1996). Acta Cryst. C52, 593–595. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Ülkü, D., Tahir, M. N. & Movsumov, E. M. (1996). Acta Cryst. C52, 2678–2680. CSD CrossRef Web of Science IUCr Journals Google Scholar

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page m580

doi:10.1107/S1600536809015074

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