catena-[[(nitrato-κO)silver(I)]-μ-1,10-phenanthroline-5,6-dione-κO,O':N,N'].

In the title one-dimensional coordination polymer, [Ag(NO(3))(C(12)H(6)N(2)O(2))](n), the Ag(I) atom is penta-coordinated by two N atoms from a 1,10-phenanthroline-5,6-dione (phen-dione) ligand, one O atom from the nitrate anion and two O atoms from another phen-dione ligand. The coordination environment around silver is slightly distorted square-pyramidal. Inter-estingly, the Ag-O distances to the phen-dione ligand are different [Ag-O = 2.612 (6) and 2.470 (5) Å]. The one-dimensional chains run parallel to [101] and are further inter-connected by weak hydrogen bonds (C-H⋯O) and π-π stacking inter-actions [centroid-centroid distances 3.950 (4) and 3.792 (4) Å], forming a three-dimensional supra-molecular network.

Related literature

For the use of 1,10-phenanthroline-5,6-dione (n class="Chemical">phen-dione) as an efficient chelating ligand establishing coordination polymers, see: Calderazzo et al. (2002 ▶); Wu et al. (1996 ▶); Liu & Xu (2006 ▶); Li et al. (2005 ▶). For examples of complexes with N,O-coordination of phen-dione, see: Paw & Eisenberg (1997 ▶); Ruiz et al. (1999 ▶); Shavaleev et al. (2003 ▶). For the synthesis of phen-dione, see: Paw & Eisenberg (1997 ▶). For the structure of a related phen-dione complex of AgI, see: Onuegbu et al. (2009 ▶). For a comparison of Ag—O bond lengths, see: Young & Hanton (2008 ▶); Sun et al. (2010 ▶); Wang et al. (2011 ▶).

Experimental

Crystal data

[Ag(NO3)(C12H6N2O2)]

M = 380.07

Monoclinic,

a = 9.5058 (14) Å

b = 10.4647 (15) Å

c = 12.1615 (17) Å

β = 99.766 (2)°

V = 1192.2 (3) Å3

Z = 4

Mo Kα radiation

μ = 1.72 mm−1

T = 296 K

0.3 × 0.2 × 0.1 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.66, T max = 0.84

6626 measured reflections

2307 independent reflections

1374 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.124

S = 1.00

2307 reflections

190 parameters

32 restraints

H-atom parameters constrained

Δρmax = 0.84 e Å−3

Δρmin = −1.05 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811020939/im2282sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811020939/im2282Isup2.hkl

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

[Ag(NO3)(C12H6N2O2)]	F(000) = 744
Mr = 380.07	Dx = 2.117 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1252 reflections
a = 9.5058 (14) Å	θ = 2.6–22.6°
b = 10.4647 (15) Å	µ = 1.72 mm−1
c = 12.1615 (17) Å	T = 296 K
β = 99.766 (2)°	Block, yellow
V = 1192.2 (3) Å3	0.3 × 0.2 × 0.1 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	2307 independent reflections
Radiation source: fine-focus sealed tube	1374 reflections with I > 2σ(I)
graphite	Rint = 0.041
Detector resolution: 0 pixels mm-1	θmax = 26.0°, θmin = 2.6°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker 2000)	k = −12→12
Tmin = 0.66, Tmax = 0.84	l = −14→7
6626 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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0445P)2 + 3.5057P] where P = (Fo2 + 2Fc2)/3
2307 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.84 e Å−3
32 restraints	Δρmin = −1.05 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	0.20025 (7)	0.15378 (7)	0.49084 (6)	0.0703 (3)
C1	0.3824 (8)	−0.0492 (8)	0.3745 (6)	0.055 (2)
H1	0.3348	−0.1065	0.4136	0.066*
C2	0.4710 (9)	−0.0969 (8)	0.3058 (7)	0.060 (2)
H2	0.4815	−0.1846	0.2981	0.072*
C3	0.5436 (8)	−0.0134 (7)	0.2488 (6)	0.0489 (19)
H3	0.6034	−0.0437	0.2015	0.059*
C4	0.5264 (7)	0.1159 (6)	0.2628 (6)	0.0399 (17)
C5	0.6048 (7)	0.2087 (6)	0.2031 (6)	0.0449 (18)
C6	0.5831 (7)	0.3489 (6)	0.2189 (5)	0.0416 (16)
C7	0.4826 (7)	0.3887 (7)	0.2938 (5)	0.0391 (17)
C8	0.4591 (7)	0.5165 (7)	0.3107 (6)	0.0485 (19)
H8	0.5058	0.5787	0.2758	0.058*
C9	0.3654 (8)	0.5503 (8)	0.3800 (6)	0.053 (2)
H9	0.3460	0.6358	0.3918	0.064*
C10	0.3008 (8)	0.4552 (8)	0.4318 (6)	0.056 (2)
H10	0.2393	0.4790	0.4801	0.067*
C11	0.4114 (7)	0.2975 (6)	0.3479 (5)	0.0356 (16)
C12	0.4337 (7)	0.1596 (7)	0.3331 (5)	0.0380 (15)
N1	0.3214 (6)	0.3316 (6)	0.4165 (5)	0.0439 (14)
N2	0.3618 (6)	0.0775 (6)	0.3874 (5)	0.0424 (14)
N3	−0.1319 (8)	0.2293 (8)	0.4504 (7)	0.0784 (15)
O1	0.6449 (5)	0.4259 (5)	0.1699 (4)	0.0567 (14)
O2	0.6867 (6)	0.1721 (5)	0.1428 (5)	0.0708 (17)
O3	−0.0348 (6)	0.2265 (7)	0.3995 (6)	0.0846 (15)
O4	−0.1158 (8)	0.1860 (9)	0.5450 (7)	0.126 (2)
O5	−0.2488 (6)	0.2729 (7)	0.4152 (5)	0.0896 (18)

	U11	U22	U33	U12	U13	U23
Ag1	0.0779 (5)	0.0783 (5)	0.0691 (5)	0.0005 (4)	0.0539 (4)	−0.0004 (4)
C1	0.062 (5)	0.052 (5)	0.057 (5)	−0.006 (4)	0.027 (4)	0.012 (4)
C2	0.066 (5)	0.047 (5)	0.071 (6)	0.003 (4)	0.023 (5)	0.004 (4)
C3	0.048 (4)	0.052 (5)	0.051 (5)	0.008 (4)	0.017 (4)	−0.006 (4)
C4	0.040 (4)	0.042 (4)	0.040 (4)	0.007 (3)	0.016 (3)	−0.004 (3)
C5	0.047 (4)	0.052 (5)	0.041 (4)	0.001 (3)	0.022 (4)	0.001 (3)
C6	0.040 (4)	0.053 (4)	0.035 (4)	−0.006 (4)	0.015 (3)	0.002 (4)
C7	0.040 (4)	0.047 (4)	0.034 (4)	−0.003 (3)	0.016 (3)	0.001 (3)
C8	0.053 (4)	0.046 (5)	0.051 (5)	−0.002 (4)	0.020 (4)	0.004 (4)
C9	0.069 (5)	0.042 (4)	0.053 (5)	0.009 (4)	0.019 (4)	−0.004 (4)
C10	0.062 (5)	0.064 (6)	0.048 (5)	0.012 (4)	0.027 (4)	−0.002 (4)
C11	0.038 (4)	0.042 (4)	0.029 (4)	0.005 (3)	0.013 (3)	−0.004 (3)
C12	0.036 (3)	0.045 (4)	0.035 (4)	−0.003 (3)	0.011 (3)	−0.003 (3)
N1	0.045 (3)	0.045 (4)	0.047 (4)	0.003 (3)	0.024 (3)	−0.002 (3)
N2	0.044 (3)	0.042 (4)	0.045 (3)	0.001 (3)	0.019 (3)	0.003 (3)
N3	0.054 (3)	0.111 (4)	0.077 (3)	0.003 (3)	0.029 (3)	0.021 (3)
O1	0.059 (3)	0.058 (3)	0.062 (3)	−0.008 (3)	0.034 (3)	0.002 (3)
O2	0.088 (4)	0.066 (4)	0.075 (4)	0.012 (3)	0.062 (3)	0.003 (3)
O3	0.061 (3)	0.108 (4)	0.092 (3)	0.006 (3)	0.036 (3)	0.009 (3)
O4	0.095 (4)	0.188 (5)	0.092 (4)	−0.022 (4)	0.012 (3)	0.058 (4)
O5	0.059 (3)	0.131 (5)	0.078 (4)	0.022 (3)	0.010 (3)	−0.017 (3)

Ag1—N2	2.287 (5)	C6—C7	1.487 (8)
Ag1—O3	2.442 (6)	C7—C8	1.377 (10)
Ag1—N1	2.442 (6)	C7—C11	1.397 (9)
Ag1—O1i	2.470 (5)	C8—C9	1.372 (10)
C1—N2	1.354 (10)	C8—H8	0.9300
C1—C2	1.376 (10)	C9—C10	1.376 (10)
C1—H1	0.9300	C9—H9	0.9300
C2—C3	1.372 (10)	C10—N1	1.326 (9)
C2—H2	0.9300	C10—H10	0.9300
C3—C4	1.377 (9)	C11—N1	1.341 (7)
C3—H3	0.9300	C11—C12	1.474 (10)
C4—C12	1.405 (8)	C12—N2	1.340 (8)
C4—C5	1.486 (9)	N3—O3	1.195 (8)
C5—O2	1.218 (7)	N3—O5	1.210 (9)
C5—C6	1.499 (7)	N3—O4	1.222 (9)
C6—O1	1.211 (7)	O1—Ag1ii	2.470 (5)
N2—Ag1—O3	120.4 (2)	C9—C8—C7	118.7 (7)
N2—Ag1—N1	70.10 (19)	C9—C8—H8	120.6
O3—Ag1—N1	92.7 (2)	C7—C8—H8	120.6
N2—Ag1—O1i	129.06 (19)	C8—C9—C10	118.8 (7)
O3—Ag1—O1i	101.00 (18)	C8—C9—H9	120.6
N1—Ag1—O1i	140.18 (19)	C10—C9—H9	120.6
N2—C1—C2	122.8 (7)	N1—C10—C9	123.5 (6)
N2—C1—H1	118.6	N1—C10—H10	118.2
C2—C1—H1	118.6	C9—C10—H10	118.2
C1—C2—C3	119.2 (7)	N1—C11—C7	121.5 (6)
C1—C2—H2	120.4	N1—C11—C12	117.2 (6)
C3—C2—H2	120.4	C7—C11—C12	121.3 (6)
C2—C3—C4	118.9 (7)	N2—C12—C4	121.1 (6)
C2—C3—H3	120.6	N2—C12—C11	118.1 (5)
C4—C3—H3	120.6	C4—C12—C11	120.8 (6)
C3—C4—C12	119.7 (7)	C10—N1—C11	118.2 (6)
C3—C4—C5	120.1 (6)	C10—N1—Ag1	127.0 (4)
C12—C4—C5	120.2 (6)	C11—N1—Ag1	114.7 (4)
O2—C5—C4	120.9 (6)	C12—N2—C1	118.3 (6)
O2—C5—C6	120.0 (6)	C12—N2—Ag1	119.6 (4)
C4—C5—C6	119.1 (5)	C1—N2—Ag1	122.0 (4)
O1—C6—C7	122.1 (6)	O3—N3—O5	124.7 (9)
O1—C6—C5	119.9 (6)	O3—N3—O4	119.6 (9)
C7—C6—C5	118.0 (6)	O5—N3—O4	115.7 (8)
C8—C7—C11	119.3 (6)	C6—O1—Ag1ii	113.8 (4)
C8—C7—C6	120.0 (6)	N3—O3—Ag1	120.0 (6)
C11—C7—C6	120.7 (6)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O4iii	0.93	2.37	3.21 (1)	149.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O4i	0.93	2.37	3.21 (1)	149

Symmetry code: (i) .