catena-Poly[bis­(μ3-2-methyl­benzoato)disilver(I)]

Danish, M.; Tahir, M.N.; Ghafoor, S.; Ahmad, N.; Nisa, M.

doi:10.1107/S1600536811016801

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 6| June 2011| Pages m734-m735

doi:10.1107/S1600536811016801

Open

access

catena-Poly[bis(μ₃-2-methylbenzoato)disilver(I)]

Muhammad Danish,^a M. Nawaz Tahir,^b ^* Sabiha Ghafoor,^c Nazir Ahmad ^c and Mehwish Nisa ^c

^aDepartment of Chemistry, University of Gujrat, Department of Chemistry, Hafiz Hayat Campus, Gujrat, Pakistan, ^bDepartment of Physics, University of Sargodha, Sargodha, Pakistan, and ^cDepartment of Chemistry, University of Sargodha, Sargodha, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 27 March 2011; accepted 4 May 2011; online 7 May 2011)

The crystal structure of the title compound, [Ag₂(C₈H₇O₂)₂]_n, features polymeric chains extending along the a axis, with the two Ag⁺ cations in a distorted trigonal coordination. The range of Ag—O bond lengths is 2.169 (2)–2.433 (2) Å, whereas the Ag⋯Ag separations are in the range 2.8674 (4)–3.6256 (5) Å. The 2-methylbenzoate groups are oriented at a dihedral angle of 60.7 (1)° with respect to each other.

Related literature

For metal complexes of o-toluic acid, see: Danish et al. (2010a ,b ,c ). For the crystal structures of related silver complexes, see: Tahir et al. (1996 , 2009 ); Ülkü et al. (1996 ).

Experimental

Crystal data

[Ag₂(C₈H₇O₂)₂]
M_r = 486.01
Monoclinic, P 2₁ /c
a = 5.6607 (3) Å
b = 27.1493 (18) Å
c = 10.2455 (7) Å
β = 100.538 (3)°
V = 1548.01 (17) Å³
Z = 4
Mo Kα radiation
μ = 2.54 mm⁻¹
T = 296 K
0.28 × 0.15 × 0.13 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.465, T_max = 0.555
12447 measured reflections
3486 independent reflections
2487 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.061
S = 1.04
3486 reflections
201 parameters
H-atom parameters constrained
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.54 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Ag1—O1	2.433 (2)
Ag1—O3	2.268 (2)
Ag1—O2ⁱ	2.169 (2)
Ag2—O1	2.305 (2)
Ag2—O3	2.414 (2)
Ag2—O4ⁱⁱ	2.186 (3)

O1—Ag1—O3	79.34 (8)
O1—Ag1—O2ⁱ	121.02 (8)
O2ⁱ—Ag1—O3	153.38 (10)
O1—Ag2—O3	79.04 (8)
O1—Ag2—O4ⁱⁱ	149.80 (9)
O3—Ag2—O4ⁱⁱ	122.08 (9)
Ag1—O1—Ag2	99.83 (9)
Ag1—O3—Ag2	101.47 (9)
Symmetry codes: (i) x+1, y, z; (ii) x-1, y, z.

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811016801/ez2241sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811016801/ez2241Isup2.hkl

checkCIF report

Comment top

The title compound (I, Fig. 1) is a continuation of our work on the synthesis of metal complexes of o-toluic acid, where we have reported the crystal structures of (II), catena-poly[[trimethyltin(IV)]-µ-2-methylbenzoato-κ²O:O^'] (Danish et al., 2010a), (III), tetrakis(-2-methylbenzoato-κ²O:O^')bis[(methanol-κO)copper(II)] (Danish et al., 2010b) and (IV), octamethylbis(2–2-methylbenzoato-κ²O:O^')bis(2-methylbenzoato-κO) di-µ₃-oxido-tetratin(IV) (Danish et al., 2010c).

We have also reported the crystal structures of silver complexes such as (V), poly[bis(p-nitrosalicylato-O:O^')disilver(I)—O³:Ag';Ag:O^3'] (Tahir et al., 1996), (VI), poly[bis(3,5-dinitrobenzoato-O¹:O²)disilver(I)—O²:Ag;Ag^':O^2'] (Ülkü et al., 1996) and (VII), poly[(µ-benzene-1,2,4,5-tetracarboxylato)tetrasilver(I)] (Tahir et al., 2009).

In the title compound, the toluine groups A (C2—C8) and B (C10—C16) are planar with r.m.s. deviation of 0.0063 and 0.0086 Å. The carboxylate groups C (O1/C1/O2) and D (O3/C9/O4) are of course planar with dihedral angles between A/C, B/D & A/B of 34.6 (3)°, 37.5 (3)° and 60.7 (1)°, respectively. The title compound essentially consists of non-centrosymmetric dimers with central core E (Ag1/O2/C1/O1/Ag2/O4/C9/O3) which is not planar (Fig. 1). These dimers are interlinked via Ag—O bonds to form one-dimensional polymeric chains extending along the a-axis (Fig. 2). The parallel polymeric chains are further interlinked by Ag—O bonds into dimeric polymeric chains. In the central core the range of Ag—O bond distances is 2.268 (2)–2.433 (2) Å whereas to adjacent units they are 2.169 (2) and 2.186 (3) Å. The Ag···Ag distance for the central core is 2.8674 (4) Å, whereas it is 3.6256 (5) Å for the symmetry related adjacent units forming the four membered ring F (Ag₂O₂). The Ag···Ag separations for adjacent chains are 3.1292 (6) and 3.2314 (6) Å. The important bond distances and angles are given in Table 1.

Related literature top

For metal complexes of o-toluic acid, see: Danish et al. (2010a,b,c). For the crystal structures of related silver complexes, see: Tahir et al. (1996, 2009); Ülkü et al. (1996).

Experimental top

Aqueous solutions of silver nitrate (0.17 g, 1.0 mmol) and the sodium salt of o-toluic acid (0.122 g, 1.0 mmol) were prepared separately in 5.0 and 10.0 ml of water, respectively. The aqueous silver nitrate was added dropwise to the solution of the sodium salt of o-toluic acid with continuous stirring until a white precipitate appeared. The reaction mixture was filtered after treatment with liquid ammonia. It was concentrated and kept in the dark for crystallization. White needle-like crystals appeared within two months.

Melting point: 473 K.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. View of the title compound with the atom numbering scheme. The thermal ellipsoids are drawn at the 50% probability level.
	Fig. 2. A partial packing diagram (PLATON; Spek, 2009) which shows that the molecules are interlinked to form polymeric chains.
	Fig. 3. A partial packing diagram (PLATON; Spek, 2009) which shows that the polymeric chains are linked into pairs.

catena-Poly[bis(µ₃-2-methylbenzoato)disilver(I)] top

Crystal data top

[Ag₂(C₈H₇O₂)₂]	F(000) = 944
M_r = 486.01	D_x = 2.085 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2487 reflections
a = 5.6607 (3) Å	θ = 3.0–27.6°
b = 27.1493 (18) Å	µ = 2.54 mm⁻¹
c = 10.2455 (7) Å	T = 296 K
β = 100.538 (3)°	Needle, colorless
V = 1548.01 (17) Å³	0.28 × 0.15 × 0.13 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	3486 independent reflections
Radiation source: fine-focus sealed tube	2487 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
Detector resolution: 7.60 pixels mm^-1	θ_max = 27.6°, θ_min = 3.0°
ω scans	h = −6→7
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −30→35
T_min = 0.465, T_max = 0.555	l = −13→13
12447 measured reflections

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) = 0.061	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0203P)²] where P = (F_o² + 2F_c²)/3
3486 reflections	(Δ/σ)_max = 0.001
201 parameters	Δρ_max = 0.44 e Å⁻³
0 restraints	Δρ_min = −0.54 e Å⁻³

Crystal data top

[Ag₂(C₈H₇O₂)₂]	V = 1548.01 (17) Å³
M_r = 486.01	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.6607 (3) Å	µ = 2.54 mm⁻¹
b = 27.1493 (18) Å	T = 296 K
c = 10.2455 (7) Å	0.28 × 0.15 × 0.13 mm
β = 100.538 (3)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3486 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2487 reflections with I > 2σ(I)
T_min = 0.465, T_max = 0.555	R_int = 0.036
12447 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.061	H-atom parameters constrained
S = 1.04	Δρ_max = 0.44 e Å⁻³
3486 reflections	Δρ_min = −0.54 e Å⁻³
201 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
Ag1	1.07402 (5)	0.04830 (1)	0.59037 (3)	0.0523 (1)
Ag2	0.51817 (5)	−0.00478 (1)	0.65370 (3)	0.0479 (1)
O1	0.6443 (4)	0.06445 (8)	0.5558 (3)	0.0400 (9)
O2	0.3299 (4)	0.10785 (8)	0.5914 (3)	0.0575 (12)
O3	0.9407 (4)	−0.02228 (8)	0.6706 (3)	0.0422 (9)
O4	1.3029 (4)	−0.03844 (9)	0.7865 (3)	0.0552 (10)
C1	0.5350 (6)	0.10473 (12)	0.5654 (3)	0.0377 (12)
C2	0.6596 (5)	0.15172 (11)	0.5403 (3)	0.0342 (11)
C3	0.8070 (6)	0.15067 (13)	0.4455 (4)	0.0464 (14)
C4	0.9228 (7)	0.19266 (16)	0.4135 (4)	0.0632 (17)
C5	0.8928 (8)	0.23558 (16)	0.4780 (6)	0.075 (2)
C6	0.7493 (7)	0.23710 (14)	0.5728 (5)	0.0678 (18)
C7	0.6290 (6)	0.19559 (13)	0.6056 (4)	0.0496 (14)
C8	0.4769 (7)	0.19959 (15)	0.7121 (5)	0.078 (2)
C9	1.0825 (6)	−0.04380 (12)	0.7643 (4)	0.0347 (12)
C10	0.9718 (6)	−0.07847 (12)	0.8498 (4)	0.0362 (11)
C11	0.7793 (6)	−0.10729 (12)	0.7884 (4)	0.0491 (14)
C12	0.6741 (7)	−0.14127 (14)	0.8585 (5)	0.0678 (19)
C13	0.7550 (8)	−0.14592 (16)	0.9913 (6)	0.076 (2)
C14	0.9405 (9)	−0.11792 (16)	1.0530 (5)	0.0698 (19)
C15	1.0591 (7)	−0.08369 (13)	0.9848 (4)	0.0482 (16)
C16	1.2646 (8)	−0.05403 (15)	1.0582 (5)	0.0762 (19)
H3	0.82809	0.12119	0.40290	0.0558*
H4	1.01920	0.19166	0.34913	0.0756*
H5	0.97014	0.26403	0.45779	0.0903*
H6	0.73227	0.26667	0.61591	0.0815*
H8A	0.51961	0.17373	0.77593	0.1167*
H8B	0.31020	0.19663	0.67235	0.1167*
H8C	0.50419	0.23095	0.75550	0.1167*
H11	0.72115	−0.10338	0.69809	0.0586*
H12	0.54878	−0.16090	0.81582	0.0812*
H13	0.68275	−0.16843	1.04006	0.0910*
H14	0.99129	−0.12151	1.14409	0.0837*
H16A	1.23586	−0.01969	1.03935	0.1139*
H16B	1.41064	−0.06385	1.03049	0.1139*
H16C	1.27876	−0.05956	1.15189	0.1139*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.0348 (2)	0.0527 (2)	0.0712 (3)	−0.0063 (1)	0.0144 (2)	0.0106 (2)
Ag2	0.0333 (2)	0.0541 (2)	0.0570 (2)	−0.0083 (1)	0.0100 (1)	0.0043 (2)
O1	0.0319 (13)	0.0331 (13)	0.0546 (18)	−0.0010 (10)	0.0068 (11)	0.0059 (11)
O2	0.0373 (15)	0.0417 (15)	0.098 (3)	−0.0036 (11)	0.0243 (14)	0.0008 (14)
O3	0.0315 (13)	0.0450 (14)	0.0498 (18)	−0.0013 (11)	0.0068 (12)	0.0130 (12)
O4	0.0298 (14)	0.0739 (19)	0.060 (2)	−0.0071 (12)	0.0036 (12)	0.0187 (14)
C1	0.038 (2)	0.037 (2)	0.036 (2)	−0.0049 (16)	0.0015 (16)	0.0030 (16)
C2	0.0287 (18)	0.0309 (19)	0.040 (2)	−0.0002 (14)	−0.0016 (15)	0.0043 (16)
C3	0.046 (2)	0.040 (2)	0.053 (3)	−0.0019 (17)	0.0085 (18)	0.0061 (19)
C4	0.058 (3)	0.061 (3)	0.074 (3)	−0.003 (2)	0.021 (2)	0.022 (2)
C5	0.073 (3)	0.043 (3)	0.110 (5)	−0.018 (2)	0.016 (3)	0.015 (3)
C6	0.074 (3)	0.037 (2)	0.089 (4)	−0.007 (2)	0.006 (3)	−0.007 (2)
C7	0.053 (2)	0.040 (2)	0.053 (3)	−0.0025 (18)	0.002 (2)	−0.0024 (19)
C8	0.093 (4)	0.072 (3)	0.073 (4)	−0.004 (3)	0.028 (3)	−0.027 (3)
C9	0.032 (2)	0.035 (2)	0.037 (2)	0.0027 (16)	0.0064 (16)	0.0004 (16)
C10	0.0333 (19)	0.036 (2)	0.041 (2)	0.0093 (16)	0.0114 (16)	0.0070 (17)
C11	0.043 (2)	0.043 (2)	0.062 (3)	−0.0039 (18)	0.0111 (19)	0.011 (2)
C12	0.057 (3)	0.054 (3)	0.095 (4)	−0.006 (2)	0.021 (3)	0.019 (3)
C13	0.080 (4)	0.062 (3)	0.097 (5)	0.005 (3)	0.044 (3)	0.032 (3)
C14	0.099 (4)	0.069 (3)	0.047 (3)	0.026 (3)	0.028 (3)	0.026 (2)
C15	0.062 (3)	0.043 (2)	0.041 (3)	0.0166 (19)	0.013 (2)	0.0033 (19)
C16	0.102 (4)	0.081 (3)	0.040 (3)	0.007 (3)	−0.002 (3)	−0.007 (2)

Geometric parameters (Å, º) top

Ag1—O1	2.433 (2)	C10—C15	1.388 (6)
Ag1—O3	2.268 (2)	C11—C12	1.370 (6)
Ag1—O2ⁱ	2.169 (2)	C12—C13	1.360 (8)
Ag2—O1	2.305 (2)	C13—C14	1.356 (7)
Ag2—O3	2.414 (2)	C14—C15	1.405 (6)
Ag2—O4ⁱⁱ	2.186 (3)	C15—C16	1.499 (6)
O1—C1	1.269 (4)	C3—H3	0.9300
O2—C1	1.241 (4)	C4—H4	0.9300
O3—C9	1.275 (5)	C5—H5	0.9300
O4—C9	1.235 (4)	C6—H6	0.9300
C1—C2	1.503 (4)	C8—H8A	0.9600
C2—C3	1.392 (5)	C8—H8B	0.9600
C2—C7	1.392 (5)	C8—H8C	0.9600
C3—C4	1.384 (6)	C11—H11	0.9300
C4—C5	1.365 (6)	C12—H12	0.9300
C5—C6	1.376 (7)	C13—H13	0.9300
C6—C7	1.389 (5)	C14—H14	0.9300
C7—C8	1.512 (6)	C16—H16A	0.9600
C9—C10	1.499 (5)	C16—H16B	0.9600
C10—C11	1.395 (5)	C16—H16C	0.9600

O1—Ag1—O3	79.34 (8)	C11—C12—C13	119.2 (4)
O1—Ag1—O2ⁱ	121.02 (8)	C12—C13—C14	120.3 (5)
O2ⁱ—Ag1—O3	153.38 (10)	C13—C14—C15	122.6 (5)
O1—Ag2—O3	79.04 (8)	C10—C15—C14	116.6 (4)
O1—Ag2—O4ⁱⁱ	149.80 (9)	C10—C15—C16	123.2 (4)
O3—Ag2—O4ⁱⁱ	122.08 (9)	C14—C15—C16	120.2 (4)
Ag1—O1—Ag2	99.83 (9)	C2—C3—H3	119.00
Ag1—O1—C1	129.2 (2)	C4—C3—H3	119.00
Ag2—O1—C1	118.4 (2)	C3—C4—H4	121.00
Ag1ⁱⁱ—O2—C1	126.8 (2)	C5—C4—H4	121.00
Ag1—O3—Ag2	101.47 (9)	C4—C5—H5	120.00
Ag1—O3—C9	117.0 (2)	C6—C5—H5	120.00
Ag2—O3—C9	128.6 (2)	C5—C6—H6	119.00
Ag2ⁱ—O4—C9	126.4 (3)	C7—C6—H6	119.00
O1—C1—O2	124.3 (3)	C7—C8—H8A	109.00
O1—C1—C2	117.9 (3)	C7—C8—H8B	109.00
O2—C1—C2	117.8 (3)	C7—C8—H8C	109.00
C1—C2—C3	117.5 (3)	H8A—C8—H8B	109.00
C1—C2—C7	122.7 (3)	H8A—C8—H8C	110.00
C3—C2—C7	119.7 (3)	H8B—C8—H8C	109.00
C2—C3—C4	121.3 (3)	C10—C11—H11	119.00
C3—C4—C5	118.8 (4)	C12—C11—H11	119.00
C4—C5—C6	120.6 (4)	C11—C12—H12	120.00
C5—C6—C7	121.7 (4)	C13—C12—H12	120.00
C2—C7—C6	117.9 (3)	C12—C13—H13	120.00
C2—C7—C8	123.1 (3)	C14—C13—H13	120.00
C6—C7—C8	119.0 (3)	C13—C14—H14	119.00
O3—C9—O4	124.1 (3)	C15—C14—H14	119.00
O3—C9—C10	117.1 (3)	C15—C16—H16A	109.00
O4—C9—C10	118.9 (3)	C15—C16—H16B	109.00
C9—C10—C11	117.7 (3)	C15—C16—H16C	109.00
C9—C10—C15	122.4 (3)	H16A—C16—H16B	109.00
C11—C10—C15	119.9 (3)	H16A—C16—H16C	109.00
C10—C11—C12	121.3 (4)	H16B—C16—H16C	109.00

O3—Ag1—O1—Ag2	4.46 (10)	Ag2ⁱ—O4—C9—C10	164.8 (2)
O3—Ag1—O1—C1	144.3 (3)	O1—C1—C2—C3	33.9 (4)
O2ⁱ—Ag1—O1—Ag2	−157.03 (10)	O1—C1—C2—C7	−147.5 (3)
O2ⁱ—Ag1—O1—C1	−17.2 (3)	O2—C1—C2—C3	−144.7 (3)
O1—Ag1—O3—Ag2	−4.28 (10)	O2—C1—C2—C7	34.0 (5)
O1—Ag1—O3—C9	−149.1 (3)	C1—C2—C3—C4	178.1 (3)
O2ⁱ—Ag1—O3—Ag2	138.32 (17)	C7—C2—C3—C4	−0.7 (5)
O2ⁱ—Ag1—O3—C9	−6.5 (4)	C1—C2—C7—C6	−178.7 (3)
O1—Ag1—O2ⁱ—C1ⁱ	−155.1 (3)	C1—C2—C7—C8	2.9 (5)
O3—Ag1—O2ⁱ—C1ⁱ	69.1 (4)	C3—C2—C7—C6	−0.1 (5)
O3—Ag2—O1—Ag1	−4.20 (10)	C3—C2—C7—C8	−178.5 (4)
O3—Ag2—O1—C1	−149.6 (3)	C2—C3—C4—C5	0.8 (6)
O4ⁱⁱ—Ag2—O1—Ag1	133.77 (16)	C3—C4—C5—C6	−0.2 (7)
O4ⁱⁱ—Ag2—O1—C1	−11.6 (4)	C4—C5—C6—C7	−0.5 (7)
O1—Ag2—O3—Ag1	4.53 (11)	C5—C6—C7—C2	0.7 (6)
O1—Ag2—O3—C9	143.6 (3)	C5—C6—C7—C8	179.1 (4)
O4ⁱⁱ—Ag2—O3—Ag1	−152.06 (10)	O3—C9—C10—C11	37.4 (5)
O4ⁱⁱ—Ag2—O3—C9	−13.0 (3)	O3—C9—C10—C15	−144.7 (4)
O1—Ag2—O4ⁱⁱ—C9ⁱⁱ	73.6 (4)	O4—C9—C10—C11	−141.2 (4)
O3—Ag2—O4ⁱⁱ—C9ⁱⁱ	−157.3 (3)	O4—C9—C10—C15	36.7 (5)
Ag1—O1—C1—O2	−153.9 (3)	C9—C10—C11—C12	177.4 (3)
Ag1—O1—C1—C2	27.7 (4)	C15—C10—C11—C12	−0.5 (5)
Ag2—O1—C1—O2	−20.2 (4)	C9—C10—C15—C14	−179.2 (4)
Ag2—O1—C1—C2	161.5 (2)	C9—C10—C15—C16	2.4 (6)
Ag1ⁱⁱ—O2—C1—O1	−12.7 (5)	C11—C10—C15—C14	−1.4 (5)
Ag1ⁱⁱ—O2—C1—C2	165.7 (2)	C11—C10—C15—C16	−179.8 (3)
Ag1—O3—C9—O4	−22.9 (5)	C10—C11—C12—C13	1.9 (6)
Ag1—O3—C9—C10	158.5 (2)	C11—C12—C13—C14	−1.3 (7)
Ag2—O3—C9—O4	−156.8 (3)	C12—C13—C14—C15	−0.8 (7)
Ag2—O3—C9—C10	24.7 (4)	C13—C14—C15—C10	2.1 (6)
Ag2ⁱ—O4—C9—O3	−13.8 (5)	C13—C14—C15—C16	−179.5 (4)

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

Experimental details

Crystal data
Chemical formula	[Ag₂(C₈H₇O₂)₂]
M_r	486.01
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	5.6607 (3), 27.1493 (18), 10.2455 (7)
β (°)	100.538 (3)
V (Å³)	1548.01 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.54
Crystal size (mm)	0.28 × 0.15 × 0.13

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.465, 0.555
No. of measured, independent and observed [I > 2σ(I)] reflections	12447, 3486, 2487
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.652

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.061, 1.04
No. of reflections	3486
No. of parameters	201
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.54

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Selected geometric parameters (Å, º) top

Ag1—O1	2.433 (2)	Ag2—O1	2.305 (2)
Ag1—O3	2.268 (2)	Ag2—O3	2.414 (2)
Ag1—O2ⁱ	2.169 (2)	Ag2—O4ⁱⁱ	2.186 (3)

O1—Ag1—O3	79.34 (8)	O1—Ag2—O4ⁱⁱ	149.80 (9)
O1—Ag1—O2ⁱ	121.02 (8)	O3—Ag2—O4ⁱⁱ	122.08 (9)
O2ⁱ—Ag1—O3	153.38 (10)	Ag1—O1—Ag2	99.83 (9)
O1—Ag2—O3	79.04 (8)	Ag1—O3—Ag2	101.47 (9)

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

Acknowledgements

The authors acknowledge the provision of funds for the purchase of the diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan.

References

Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Danish, M., Ghafoor, S., Tahir, M. N., Ahmad, N. & Hamid, M. (2010a). Acta Cryst. E66, m1268–m1269. Web of Science CSD CrossRef IUCr Journals Google Scholar
Danish, M., Saleem, I., Ahmad, N., Starosta, W. & Leciejewicz, J. (2010b). Acta Cryst. E66, m4. Web of Science CSD CrossRef IUCr Journals Google Scholar
Danish, M., Saleem, I., Tahir, M. N., Ahmad, N. & Raza, A. R. (2010c). Acta Cryst. E66, m528. Web of Science CSD CrossRef IUCr Journals 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
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tahir, M. N., Atakol, O. & Tariq, M. I. (2009). Acta Cryst. E65, m580. Web of Science CSD CrossRef 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