Crystal structure of catena-poly[bis-[μ3-2-(2-nitro-phen-yl)acetato-κ(3) O:O:O']disilver(I)].

The title compound, [Ag2(C8H6NO4)2] n , is a silver complex of 2-(2-nitro-phen-yl)acetic acid. The mol-ecules are not conventional crystallographic inversion dimers but consist of two independent ligands and two Ag(I) ions, each with a distorted T-shaped coordination environment. The dihedral angles between acetate groups and the benzene rings are 51.1 (2) and 57.9 (2)°. The nitro groups are oriented at dihedral angles of 23.6 (5) and 32.3 (3)° with respect to the parent benzene rings. The dimers form polymeric chains along the a-axis direction. The Ag⋯Ag separation within a dimer is 2.8200 (5) and between symmetry-related dimers is 3.6182 (5) Å. The polymeric chains are inter-linked by C-H⋯O hydrogen-bond inter-actions.

Related literature

For related structures see: Danish et al. (2011a ▸,b ▸, 2015a ▸,b ▸); Li et al. (2011 ▸)

Experimental

Crystal data

[Ag2(C8H6NO4)2]

M = 576.02

Monoclinic,

a = 5.5249 (3) Å

b = 15.8838 (10) Å

c = 20.0257 (11) Å

β = 96.853 (3)°

V = 1744.83 (17) Å3

Z = 4

Mo Kα radiation

μ = 2.30 mm−1

T = 296 K

0.37 × 0.22 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▸) T min = 0.485, T max = 0.682

14170 measured reflections

3781 independent reflections

3113 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.066

S = 1.10

3781 reflections

253 parameters

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −0.55 e Å−3

Data collection: APEX2 (Bruker, 2007 ▸); cell refinement: SAINT (Bruker, 2007 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸) and PLATON (Spek, 2009 ▸); software used to prepare material for publication: WinGX (Farrugia, 2012 ▸) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015007616/fk2086sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015007616/fk2086Isup2.hkl

Click here for additional data file.

. DOI: 10.1107/S2056989015007616/fk2086fig1.tif

Mol­ecular structure of the title compound. Anisotropic displacement ellipsoids are drawn at the 50% probability level. H-atoms are shown by small circles of arbitrary radii.

Click here for additional data file.

. DOI: 10.1107/S2056989015007616/fk2086fig2.tif

Crystal packing which shows that mol­ecules form polymeric network due to inter­linkage of dimers. The dimers are inter­linked due to H-bondings. The H-atoms not involved in H-bondings are omitted for clarity.

CCDC reference: 1060272

Additional supporting information: crystallographic information; 3D view; checkCIF report

[Ag2(C8H6NO4)2]	F(000) = 1120
Mr = 576.02	Dx = 2.193 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 5.5249 (3) Å	Cell parameters from 3113 reflections
b = 15.8838 (10) Å	θ = 1.6–27.0°
c = 20.0257 (11) Å	µ = 2.30 mm−1
β = 96.853 (3)°	T = 296 K
V = 1744.83 (17) Å3	Needle, colorless
Z = 4	0.37 × 0.22 × 0.18 mm

Bruker Kappa APEXII CCD diffractometer	3781 independent reflections
Radiation source: fine-focus sealed tube	3113 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
Detector resolution: 7.80 pixels mm-1	θmax = 27.0°, θmin = 1.6°
ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −20→20
Tmin = 0.485, Tmax = 0.682	l = −25→25
14170 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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.066	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.0165P)2 + 3.0884P] where P = (Fo2 + 2Fc2)/3
3781 reflections	(Δ/σ)max < 0.001
253 parameters	Δρmax = 0.47 e Å−3
0 restraints	Δρmin = −0.55 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	0.94971 (5)	0.08333 (2)	0.04106 (2)	0.04649 (10)
Ag2	0.55095 (5)	−0.00701 (2)	0.08051 (2)	0.04710 (10)
O1	0.6850 (4)	0.17796 (16)	0.00365 (15)	0.0446 (7)
O2	0.3776 (5)	0.11268 (17)	0.04293 (16)	0.0507 (8)
O3	0.6222 (7)	0.3128 (3)	0.10446 (17)	0.0813 (12)
O4	0.9451 (7)	0.3737 (3)	0.0785 (2)	0.0857 (12)
O5	1.1302 (5)	−0.02471 (16)	0.09716 (15)	0.0455 (7)
O6	0.8165 (4)	−0.09755 (16)	0.12586 (14)	0.0422 (7)
O7	1.0110 (7)	−0.0492 (2)	0.2652 (2)	0.0769 (11)
O8	0.6646 (7)	−0.0985 (3)	0.28321 (19)	0.0891 (13)
N1	0.7356 (7)	0.3501 (2)	0.06550 (19)	0.0519 (9)
N2	0.8701 (7)	−0.1072 (3)	0.26878 (18)	0.0534 (10)
C1	0.4719 (7)	0.1752 (2)	0.0172 (2)	0.0376 (9)
C2	0.3050 (7)	0.2495 (2)	0.0012 (2)	0.0439 (10)
H2A	0.1657	0.2306	−0.0292	0.053*
H2B	0.2445	0.2672	0.0426	0.053*
C3	0.4109 (6)	0.3250 (2)	−0.02943 (19)	0.0321 (8)
C4	0.6114 (7)	0.3702 (2)	−0.00200 (19)	0.0344 (8)
C5	0.7012 (8)	0.4370 (3)	−0.0343 (3)	0.0583 (12)
H5	0.8407	0.4645	−0.0149	0.070*
C6	0.5883 (11)	0.4634 (3)	−0.0944 (3)	0.0666 (14)
H6	0.6486	0.5095	−0.1158	0.080*
C7	0.3877 (11)	0.4226 (3)	−0.1231 (2)	0.0654 (14)
H7	0.3080	0.4410	−0.1640	0.079*
C8	0.3015 (8)	0.3533 (3)	−0.0914 (2)	0.0531 (11)
H8	0.1660	0.3248	−0.1122	0.064*
C9	1.0388 (6)	−0.0834 (2)	0.12825 (19)	0.0338 (8)
C10	1.2235 (7)	−0.1397 (3)	0.1690 (2)	0.0448 (10)
H10A	1.3176	−0.1683	0.1379	0.054*
H10B	1.3352	−0.1038	0.1972	0.054*
C11	1.1271 (7)	−0.2051 (2)	0.21313 (18)	0.0333 (8)
C12	0.9564 (7)	−0.1916 (2)	0.25696 (18)	0.0366 (8)
C13	0.8654 (9)	−0.2561 (3)	0.2933 (2)	0.0609 (13)
H13	0.7455	−0.2457	0.3211	0.073*
C14	0.9568 (12)	−0.3357 (3)	0.2873 (3)	0.0778 (18)
H14	0.8973	−0.3801	0.3108	0.093*
C15	1.1325 (11)	−0.3498 (3)	0.2474 (3)	0.0747 (17)
H15	1.1997	−0.4033	0.2453	0.090*
C16	1.2119 (8)	−0.2866 (3)	0.2102 (2)	0.0518 (11)
H16	1.3281	−0.2985	0.1815	0.062*

	U11	U22	U33	U12	U13	U23
Ag1	0.02941 (16)	0.04213 (18)	0.0682 (2)	0.00658 (13)	0.00686 (14)	0.02080 (15)
Ag2	0.02920 (16)	0.04436 (18)	0.0678 (2)	0.00628 (13)	0.00618 (14)	0.02365 (16)
O1	0.0297 (14)	0.0374 (15)	0.069 (2)	0.0081 (11)	0.0160 (13)	0.0225 (13)
O2	0.0301 (14)	0.0367 (15)	0.086 (2)	−0.0014 (11)	0.0084 (14)	0.0291 (15)
O3	0.090 (3)	0.112 (3)	0.041 (2)	0.009 (2)	0.0057 (19)	0.018 (2)
O4	0.054 (2)	0.101 (3)	0.093 (3)	−0.003 (2)	−0.031 (2)	−0.015 (2)
O5	0.0312 (14)	0.0391 (15)	0.0670 (19)	0.0026 (11)	0.0095 (13)	0.0276 (13)
O6	0.0265 (14)	0.0419 (15)	0.0569 (18)	−0.0024 (11)	−0.0010 (12)	0.0243 (13)
O7	0.093 (3)	0.0350 (18)	0.096 (3)	0.0016 (18)	−0.016 (2)	−0.0170 (18)
O8	0.065 (2)	0.135 (4)	0.065 (2)	0.032 (2)	−0.0004 (19)	−0.044 (2)
N1	0.050 (2)	0.053 (2)	0.049 (2)	0.0084 (18)	−0.0069 (19)	−0.0121 (18)
N2	0.056 (2)	0.059 (2)	0.042 (2)	0.0120 (19)	−0.0094 (18)	−0.0205 (18)
C1	0.035 (2)	0.0286 (19)	0.049 (2)	0.0023 (15)	0.0027 (17)	0.0075 (16)
C2	0.0245 (19)	0.032 (2)	0.075 (3)	0.0038 (15)	0.0060 (19)	0.0145 (19)
C3	0.0283 (18)	0.0251 (17)	0.043 (2)	0.0057 (14)	0.0039 (16)	0.0032 (15)
C4	0.0321 (19)	0.0316 (19)	0.039 (2)	0.0009 (15)	0.0023 (16)	−0.0012 (15)
C5	0.054 (3)	0.042 (2)	0.081 (4)	−0.013 (2)	0.012 (3)	0.004 (2)
C6	0.096 (4)	0.039 (3)	0.070 (4)	0.002 (3)	0.033 (3)	0.018 (2)
C7	0.102 (4)	0.053 (3)	0.040 (3)	0.024 (3)	0.002 (3)	0.013 (2)
C8	0.058 (3)	0.041 (2)	0.053 (3)	0.008 (2)	−0.019 (2)	0.001 (2)
C9	0.0315 (19)	0.0311 (19)	0.038 (2)	0.0021 (15)	0.0025 (16)	0.0100 (16)
C10	0.029 (2)	0.051 (2)	0.055 (3)	0.0056 (17)	0.0051 (18)	0.022 (2)
C11	0.035 (2)	0.0276 (18)	0.035 (2)	0.0015 (14)	−0.0060 (16)	0.0048 (15)
C12	0.040 (2)	0.038 (2)	0.030 (2)	−0.0071 (16)	−0.0068 (16)	−0.0018 (15)
C13	0.071 (3)	0.081 (4)	0.029 (2)	−0.024 (3)	0.000 (2)	0.005 (2)
C14	0.111 (5)	0.052 (3)	0.063 (4)	−0.038 (3)	−0.021 (3)	0.027 (3)
C15	0.103 (5)	0.029 (2)	0.083 (4)	−0.002 (3)	−0.027 (3)	0.011 (2)
C16	0.061 (3)	0.037 (2)	0.054 (3)	0.013 (2)	−0.009 (2)	0.002 (2)

Ag1—O1	2.167 (2)	C3—C4	1.379 (5)
Ag1—O5	2.221 (2)	C3—C8	1.388 (5)
Ag1—O2i	2.405 (3)	C4—C5	1.365 (5)
Ag1—Ag2	2.8200 (4)	C5—C6	1.354 (7)
Ag1—Ag1ii	3.1998 (7)	C5—H5	0.9300
Ag2—O6	2.174 (2)	C6—C7	1.351 (7)
Ag2—O2	2.219 (3)	C6—H6	0.9300
Ag2—O5iii	2.404 (2)	C7—C8	1.384 (7)
Ag2—Ag2iv	3.2140 (7)	C7—H7	0.9300
O1—C1	1.241 (4)	C8—H8	0.9300
O2—C1	1.259 (4)	C9—C10	1.518 (5)
O2—Ag1iii	2.405 (3)	C10—C11	1.503 (5)
O3—N1	1.211 (5)	C10—H10A	0.9700
O4—N1	1.215 (5)	C10—H10B	0.9700
O5—C9	1.260 (4)	C11—C12	1.380 (5)
O5—Ag2i	2.404 (2)	C11—C16	1.380 (5)
O6—C9	1.244 (4)	C12—C13	1.386 (6)
O7—N2	1.214 (5)	C13—C14	1.373 (8)
O8—N2	1.212 (5)	C13—H13	0.9300
N1—C4	1.476 (5)	C14—C15	1.348 (8)
N2—C12	1.451 (5)	C14—H14	0.9300
C1—C2	1.509 (5)	C15—C16	1.354 (7)
C2—C3	1.498 (5)	C15—H15	0.9300
C2—H2A	0.9700	C16—H16	0.9300
C2—H2B	0.9700
O1—Ag1—O5	162.60 (9)	C4—C3—C2	126.1 (3)
O1—Ag1—O2i	119.49 (9)	C8—C3—C2	118.4 (4)
O5—Ag1—O2i	76.16 (9)	C5—C4—C3	122.4 (4)
O1—Ag1—Ag2	86.12 (7)	C5—C4—N1	116.5 (4)
O5—Ag1—Ag2	77.51 (6)	C3—C4—N1	121.0 (3)
O2i—Ag1—Ag2	153.31 (6)	C6—C5—C4	120.4 (4)
O1—Ag1—Ag1ii	123.20 (8)	C6—C5—H5	119.8
O5—Ag1—Ag1ii	61.69 (8)	C4—C5—H5	119.8
O2i—Ag1—Ag1ii	86.43 (8)	C7—C6—C5	119.8 (4)
Ag2—Ag1—Ag1ii	84.972 (15)	C7—C6—H6	120.1
O6—Ag2—O2	161.91 (10)	C5—C6—H6	120.1
O6—Ag2—O5iii	118.69 (9)	C6—C7—C8	119.7 (4)
O2—Ag2—O5iii	76.23 (9)	C6—C7—H7	120.2
O6—Ag2—Ag1	86.72 (6)	C8—C7—H7	120.2
O2—Ag2—Ag1	77.83 (6)	C7—C8—C3	122.1 (4)
O5iii—Ag2—Ag1	154.04 (6)	C7—C8—H8	119.0
O6—Ag2—Ag2iv	119.58 (8)	C3—C8—H8	119.0
O2—Ag2—Ag2iv	65.40 (9)	O6—C9—O5	124.5 (3)
O5iii—Ag2—Ag2iv	95.20 (7)	O6—C9—C10	120.8 (3)
Ag1—Ag2—Ag2iv	74.507 (13)	O5—C9—C10	114.7 (3)
C1—O1—Ag1	121.2 (2)	C11—C10—C9	117.4 (3)
C1—O2—Ag2	129.1 (2)	C11—C10—H10A	107.9
C1—O2—Ag1iii	126.9 (2)	C9—C10—H10A	107.9
Ag2—O2—Ag1iii	102.88 (10)	C11—C10—H10B	107.9
C9—O5—Ag1	129.8 (2)	C9—C10—H10B	108.0
C9—O5—Ag2i	127.3 (2)	H10A—C10—H10B	107.2
Ag1—O5—Ag2i	102.86 (9)	C12—C11—C16	115.8 (4)
C9—O6—Ag2	120.7 (2)	C12—C11—C10	125.7 (3)
O3—N1—O4	124.4 (4)	C16—C11—C10	118.5 (4)
O3—N1—C4	118.4 (4)	C11—C12—C13	122.5 (4)
O4—N1—C4	117.1 (4)	C11—C12—N2	120.7 (4)
O8—N2—O7	123.6 (4)	C13—C12—N2	116.7 (4)
O8—N2—C12	118.7 (4)	C14—C13—C12	118.3 (5)
O7—N2—C12	117.7 (4)	C14—C13—H13	120.8
O1—C1—O2	124.6 (3)	C12—C13—H13	120.8
O1—C1—C2	119.8 (3)	C15—C14—C13	120.2 (5)
O2—C1—C2	115.6 (3)	C15—C14—H14	119.9
C3—C2—C1	117.0 (3)	C13—C14—H14	119.9
C3—C2—H2A	108.0	C14—C15—C16	120.4 (5)
C1—C2—H2A	108.0	C14—C15—H15	119.8
C3—C2—H2B	108.0	C16—C15—H15	119.8
C1—C2—H2B	108.0	C15—C16—C11	122.5 (5)
H2A—C2—H2B	107.3	C15—C16—H16	118.7
C4—C3—C8	115.5 (3)	C11—C16—H16	118.7
Ag1—O1—C1—O2	−12.5 (6)	Ag2—O6—C9—O5	−11.1 (5)
Ag1—O1—C1—C2	169.0 (3)	Ag2—O6—C9—C10	170.6 (3)
Ag2—O2—C1—O1	5.5 (6)	Ag1—O5—C9—O6	9.8 (6)
Ag1iii—O2—C1—O1	−160.2 (3)	Ag2i—O5—C9—O6	−167.2 (3)
Ag2—O2—C1—C2	−175.9 (3)	Ag1—O5—C9—C10	−171.8 (3)
Ag1iii—O2—C1—C2	18.3 (5)	Ag2i—O5—C9—C10	11.2 (5)
O1—C1—C2—C3	−1.4 (6)	O6—C9—C10—C11	−8.0 (6)
O2—C1—C2—C3	−180.0 (4)	O5—C9—C10—C11	173.6 (4)
C1—C2—C3—C4	−57.6 (6)	C9—C10—C11—C12	−47.7 (6)
C1—C2—C3—C8	122.1 (4)	C9—C10—C11—C16	131.7 (4)
C8—C3—C4—C5	−1.7 (6)	C16—C11—C12—C13	−3.2 (6)
C2—C3—C4—C5	177.9 (4)	C10—C11—C12—C13	176.2 (4)
C8—C3—C4—N1	176.2 (3)	C16—C11—C12—N2	174.5 (3)
C2—C3—C4—N1	−4.1 (6)	C10—C11—C12—N2	−6.1 (6)
O3—N1—C4—C5	155.5 (4)	O8—N2—C12—C11	150.3 (4)
O4—N1—C4—C5	−23.1 (5)	O7—N2—C12—C11	−31.5 (5)
O3—N1—C4—C3	−22.5 (6)	O8—N2—C12—C13	−31.9 (5)
O4—N1—C4—C3	158.8 (4)	O7—N2—C12—C13	146.4 (4)
C3—C4—C5—C6	2.5 (7)	C11—C12—C13—C14	2.7 (6)
N1—C4—C5—C6	−175.5 (4)	N2—C12—C13—C14	−175.1 (4)
C4—C5—C6—C7	−1.0 (8)	C12—C13—C14—C15	0.7 (7)
C5—C6—C7—C8	−1.0 (8)	C13—C14—C15—C16	−3.4 (8)
C6—C7—C8—C3	1.8 (7)	C14—C15—C16—C11	2.8 (8)
C4—C3—C8—C7	−0.4 (6)	C12—C11—C16—C15	0.4 (6)
C2—C3—C8—C7	179.9 (4)	C10—C11—C16—C15	−179.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···O4iii	0.97	2.53	3.312 (6)	138
C10—H10B···O8i	0.97	2.35	3.205 (6)	146
C6—H6···O8v	0.93	2.48	3.322 (6)	151
C15—H15···O7vi	0.93	2.59	3.268 (6)	130

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C2H2BO4i	0.97	2.53	3.312(6)	138
C10H10BO8ii	0.97	2.35	3.205(6)	146
C6H6O8iii	0.93	2.48	3.322(6)	151
C15H15O7iv	0.93	2.59	3.268(6)	130

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .