catena-Poly[bis-(μ(3)-2-methyl-3,5-dinitro-benzoato)disilver(I)].

In the title coordination polymer, [Ag(2)(C(8)H(5)N(2)O(6))(2)](n), the silver ion is coordinated to three O atoms from three different anions in an approximate T-shape with one bond much longer than the other two. The polyhedral connectivity leads to [100] chains containing alternating centrosymmetric four-rings and eight-rings, with a short d(10)⋯d(10) Ag⋯Ag interaction [2.8846 (4) Å] across the latter. The nitro groups are oriented at dihedral angles of 21.2 (5) and 64.3 (3)° with respect to the aromatic ring of the ligand. A C-H⋯O inter-action occurs in the crystal.

Related literature

For background and related structures, see: Danish, Ghafoor, Ahmad et al. (2011 ▶); Danish, Ghafoor, Tahir et al. (2011 ▶); Danish, Tahir et al. (2011 ▶); Tahir et al. (1996 ▶, 2009 ▶); Ülkü et al. (1996 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

[Ag2(C8H5N2O6)2]

M = 333.01

Monoclinic,

a = 5.7073 (3) Å

b = 11.9204 (6) Å

c = 14.5117 (7) Å

β = 90.493 (2)°

V = 987.24 (9) Å3

Z = 4

Mo Kα radiation

μ = 2.06 mm−1

T = 296 K

0.32 × 0.24 × 0.22 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.560, T max = 0.630

9039 measured reflections

2406 independent reflections

1786 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.071

S = 1.02

2406 reflections

155 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.47 e Å−3

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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811022483/hb5898sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811022483/hb5898Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Ag2(C8H5N2O6)2]	F(000) = 648
Mr = 333.01	Dx = 2.240 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1786 reflections
a = 5.7073 (3) Å	θ = 2.2–28.3°
b = 11.9204 (6) Å	µ = 2.06 mm−1
c = 14.5117 (7) Å	T = 296 K
β = 90.493 (2)°	Prism, colorless
V = 987.24 (9) Å3	0.32 × 0.24 × 0.22 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	2406 independent reflections
Radiation source: fine-focus sealed tube	1786 reflections with I > 2σ(I)
graphite	Rint = 0.037
Detector resolution: 7.50 pixels mm-1	θmax = 28.3°, θmin = 2.2°
ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −15→15
Tmin = 0.560, Tmax = 0.630	l = −19→18
9039 measured reflections

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.071	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0305P)2 + 0.132P] where P = (Fo2 + 2Fc2)/3
2406 reflections	(Δ/σ)max = 0.001
155 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.47 e Å−3

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.

	x	y	z	Uiso*/Ueq
Ag1	−0.29331 (4)	−0.02958 (3)	−0.051068 (17)	0.04430 (11)
O1	−0.1299 (4)	−0.0013 (2)	0.08689 (15)	0.0381 (6)
O2	−0.4558 (4)	0.0300 (2)	0.16610 (16)	0.0459 (6)
O3	−0.1538 (7)	0.2338 (3)	0.4925 (2)	0.0946 (12)
O4	0.1858 (6)	0.2829 (3)	0.4489 (2)	0.0870 (11)
O5	0.5695 (4)	−0.0999 (3)	0.40124 (18)	0.0609 (8)
O6	0.3756 (5)	−0.2134 (2)	0.31332 (19)	0.0623 (8)
N1	0.0174 (6)	0.2210 (2)	0.4468 (2)	0.0477 (8)
N2	0.4018 (4)	−0.1237 (3)	0.35194 (18)	0.0400 (7)
C1	−0.2392 (5)	0.0204 (2)	0.1589 (2)	0.0276 (6)
C2	−0.0938 (5)	0.0338 (2)	0.24522 (19)	0.0252 (6)
C3	−0.1291 (5)	0.1216 (2)	0.3078 (2)	0.0282 (6)
C4	0.0286 (5)	0.1253 (3)	0.3821 (2)	0.0319 (7)
C5	0.2037 (5)	0.0491 (3)	0.3986 (2)	0.0341 (7)
H5	0.3050	0.0562	0.4488	0.041*
C6	0.2220 (5)	−0.0381 (3)	0.3373 (2)	0.0289 (6)
C7	0.0803 (5)	−0.0451 (2)	0.26043 (19)	0.0271 (6)
H7	0.1016	−0.1031	0.2184	0.032*
C8	−0.3140 (6)	0.2095 (3)	0.2935 (3)	0.0455 (9)
H8A	−0.3469	0.2171	0.2288	0.068*
H8B	−0.2592	0.2799	0.3175	0.068*
H8C	−0.4541	0.1877	0.3249	0.068*

	U11	U22	U33	U12	U13	U23
Ag1	0.02496 (14)	0.0754 (2)	0.03242 (15)	−0.00299 (13)	−0.00920 (10)	0.00362 (13)
O1	0.0238 (10)	0.0648 (16)	0.0257 (12)	0.0004 (10)	−0.0030 (9)	−0.0048 (10)
O2	0.0195 (10)	0.0871 (19)	0.0311 (12)	−0.0002 (11)	−0.0038 (9)	−0.0001 (12)
O3	0.122 (3)	0.078 (2)	0.085 (3)	−0.005 (2)	0.052 (2)	−0.0341 (19)
O4	0.094 (2)	0.053 (2)	0.114 (3)	−0.0129 (17)	−0.012 (2)	−0.0364 (18)
O5	0.0420 (14)	0.088 (2)	0.0518 (16)	0.0154 (14)	−0.0241 (12)	−0.0037 (14)
O6	0.0634 (17)	0.0575 (18)	0.0657 (19)	0.0282 (14)	−0.0176 (14)	−0.0220 (14)
N1	0.067 (2)	0.0365 (17)	0.0391 (17)	0.0022 (17)	−0.0016 (16)	−0.0086 (13)
N2	0.0325 (14)	0.0564 (19)	0.0311 (15)	0.0101 (14)	−0.0058 (11)	−0.0007 (13)
C1	0.0239 (14)	0.0316 (16)	0.0271 (15)	−0.0053 (13)	−0.0045 (12)	0.0057 (12)
C2	0.0201 (13)	0.0339 (17)	0.0215 (14)	−0.0055 (13)	−0.0004 (11)	0.0034 (12)
C3	0.0272 (14)	0.0289 (16)	0.0285 (16)	−0.0013 (13)	0.0051 (12)	0.0043 (12)
C4	0.0389 (17)	0.0283 (16)	0.0286 (16)	−0.0047 (14)	0.0031 (13)	−0.0035 (12)
C5	0.0374 (17)	0.0390 (19)	0.0257 (16)	−0.0034 (14)	−0.0075 (13)	−0.0031 (12)
C6	0.0230 (14)	0.0376 (18)	0.0260 (15)	0.0014 (13)	−0.0012 (12)	−0.0004 (13)
C7	0.0252 (14)	0.0330 (18)	0.0230 (14)	−0.0047 (12)	0.0009 (12)	−0.0034 (11)
C8	0.0414 (18)	0.039 (2)	0.056 (2)	0.0103 (16)	0.0047 (17)	0.0006 (16)

Ag1—O2i	2.190 (2)	C1—C2	1.505 (4)
Ag1—O1	2.227 (2)	C2—C7	1.384 (4)
Ag1—O1ii	2.502 (2)	C2—C3	1.402 (4)
Ag1—Ag1i	2.8845 (5)	C3—C4	1.399 (4)
O1—C1	1.249 (4)	C3—C8	1.500 (4)
O1—Ag1ii	2.502 (2)	C4—C5	1.370 (4)
O2—C1	1.247 (3)	C5—C6	1.373 (4)
O2—Ag1i	2.190 (2)	C5—H5	0.9300
O3—N1	1.195 (4)	C6—C7	1.375 (4)
O4—N1	1.212 (4)	C7—H7	0.9300
O5—N2	1.223 (3)	C8—H8A	0.9600
O6—N2	1.216 (4)	C8—H8B	0.9600
N1—C4	1.479 (4)	C8—H8C	0.9600
N2—C6	1.462 (4)
O2i—Ag1—O1	162.11 (8)	C4—C3—C2	115.3 (3)
O2i—Ag1—O1ii	117.90 (8)	C4—C3—C8	122.1 (3)
O1—Ag1—O1ii	76.52 (8)	C2—C3—C8	122.5 (3)
O2i—Ag1—Ag1i	81.95 (6)	C5—C4—C3	125.3 (3)
O1—Ag1—Ag1i	80.74 (6)	C5—C4—N1	115.8 (3)
O1ii—Ag1—Ag1i	150.00 (5)	C3—C4—N1	118.8 (3)
C1—O1—Ag1	125.13 (18)	C4—C5—C6	116.6 (3)
C1—O1—Ag1ii	129.30 (18)	C4—C5—H5	121.7
Ag1—O1—Ag1ii	103.48 (8)	C6—C5—H5	121.7
C1—O2—Ag1i	125.3 (2)	C5—C6—C7	121.6 (3)
O3—N1—O4	124.0 (3)	C5—C6—N2	119.5 (3)
O3—N1—C4	119.4 (3)	C7—C6—N2	118.9 (3)
O4—N1—C4	116.6 (3)	C6—C7—C2	120.3 (3)
O6—N2—O5	124.5 (3)	C6—C7—H7	119.8
O6—N2—C6	117.6 (3)	C2—C7—H7	119.8
O5—N2—C6	117.9 (3)	C3—C8—H8A	109.5
O2—C1—O1	126.3 (3)	C3—C8—H8B	109.5
O2—C1—C2	117.4 (3)	H8A—C8—H8B	109.5
O1—C1—C2	116.3 (2)	C3—C8—H8C	109.5
C7—C2—C3	120.7 (3)	H8A—C8—H8C	109.5
C7—C2—C1	116.8 (3)	H8B—C8—H8C	109.5
C3—C2—C1	122.5 (3)
O2i—Ag1—O1—C1	19.3 (5)	C2—C3—C4—C5	−2.3 (4)
O1ii—Ag1—O1—C1	164.8 (3)	C8—C3—C4—C5	−178.9 (3)
Ag1i—Ag1—O1—C1	4.5 (2)	C2—C3—C4—N1	174.6 (3)
O2i—Ag1—O1—Ag1ii	−145.5 (3)	C8—C3—C4—N1	−2.0 (4)
O1ii—Ag1—O1—Ag1ii	0.0	O3—N1—C4—C5	−118.4 (4)
Ag1i—Ag1—O1—Ag1ii	−160.29 (8)	O4—N1—C4—C5	62.5 (4)
Ag1i—O2—C1—O1	−7.0 (5)	O3—N1—C4—C3	64.4 (4)
Ag1i—O2—C1—C2	174.26 (19)	O4—N1—C4—C3	−114.7 (4)
Ag1—O1—C1—O2	−0.1 (5)	C3—C4—C5—C6	−0.8 (5)
Ag1ii—O1—C1—O2	160.7 (2)	N1—C4—C5—C6	−177.8 (3)
Ag1—O1—C1—C2	178.61 (18)	C4—C5—C6—C7	3.6 (5)
Ag1ii—O1—C1—C2	−20.6 (4)	C4—C5—C6—N2	−178.7 (3)
O2—C1—C2—C7	134.2 (3)	O6—N2—C6—C5	160.4 (3)
O1—C1—C2—C7	−44.6 (4)	O5—N2—C6—C5	−20.4 (4)
O2—C1—C2—C3	−46.2 (4)	O6—N2—C6—C7	−21.8 (4)
O1—C1—C2—C3	135.0 (3)	O5—N2—C6—C7	157.4 (3)
C7—C2—C3—C4	2.7 (4)	C5—C6—C7—C2	−3.2 (5)
C1—C2—C3—C4	−176.9 (3)	N2—C6—C7—C2	179.1 (3)
C7—C2—C3—C8	179.3 (3)	C3—C2—C7—C6	−0.2 (4)
C1—C2—C3—C8	−0.2 (4)	C1—C2—C7—C6	179.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O5iii	0.93	2.34	3.227 (4)	159

Ag1—O2i	2.190 (2)
Ag1—O1	2.227 (2)
Ag1—O1ii	2.502 (2)

O2i—Ag1—O1	162.11 (8)
O2i—Ag1—O1ii	117.90 (8)
O1—Ag1—O1ii	76.52 (8)

Symmetry codes: (i) ; (ii) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O5iii	0.93	2.34	3.227 (4)	159

Symmetry code: (iii) .