(μ-2',6'-Dicarboxy-biphenyl-2,6-dicar-boxylato)bis[(1,10-phenanthroline)silver(I)].

In the dimeric title complex, [Ag(2)(C(16)H(8)O(8))(C(12)H(8)N(2))(2)] or [Ag(2)(H(2)bta)(phen)(2)] (H(4)bta = biphenyl-2,2',6,6'-tetra-carb-ox-y-lic acid, phen = 1,10-phenanthroline), each Ag(I) ion displays an approximatively planar-trigonal geometry, being surrounded by one chelating phen ligand and one carboxyl-ate O atom from an H(2)bta ligand. Owing to the the presence of crystallographic twofold rotation axes, the four C atoms bisecting the H~2~bta ligand are located on a special position. Each H(2)bta ligand acts as a bis-monodentate ligand, ligating two Ag(I) ions into a dimeric compound. Inter-molecular O-H⋯O inter-actions are observed in the crystal structure.

Related literature

The self-assembled construction of coordination polymers is of current inter­est in the field of supra­molecular chemistry and crystal engineering owing to their potential applications as functional materials, as well as their intriguing variety of architectures and mol­ecular topologies, see: Braga et al. (1998 ▶); Yaghi et al. (1998 ▶). For related structures, see: Huang et al. (2007 ▶); Suh et al. (2006 ▶).

Experimental

Crystal data

[Ag2(C16H8O8)(C12H8N2)2]

M = 904.37

Monoclinic,

a = 11.7633 (17) Å

b = 11.5730 (18) Å

c = 24.884 (4) Å

β = 92.397 (2)°

V = 3384.7 (9) Å3

Z = 4

Mo Kα radiation

μ = 1.22 mm−1

T = 293 K

0.20 × 0.18 × 0.15 mm

Data collection

Bruker APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.792, T max = 0.838

8881 measured reflections

3300 independent reflections

1843 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.178

S = 1.04

3300 reflections

246 parameters

H-atom parameters constrained

Δρmax = 1.59 e Å−3

Δρmin = −0.97 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810037700/kp2272sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810037700/kp2272Isup2.hkl

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

[Ag2(C16H8O8)(C12H8N2)2]	F(000) = 1800
Mr = 904.37	Dx = 1.775 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 785 reflections
a = 11.7633 (17) Å	θ = 2.4–28.0°
b = 11.5730 (18) Å	µ = 1.22 mm−1
c = 24.884 (4) Å	T = 293 K
β = 92.397 (2)°	Block, colourless
V = 3384.7 (9) Å3	0.20 × 0.18 × 0.15 mm
Z = 4

Bruker APEX CCD diffractometer	3300 independent reflections
Radiation source: fine-focus sealed tube	1843 reflections with I > 2σ(I)
graphite	Rint = 0.041
phi and ω scan	θmax = 26.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −14→11
Tmin = 0.792, Tmax = 0.838	k = −14→13
8881 measured reflections	l = −30→24

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.178	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0855P)2 + 3.1208P] where P = (Fo2 + 2Fc2)/3
3300 reflections	(Δ/σ)max = 0.001
246 parameters	Δρmax = 1.59 e Å−3
0 restraints	Δρmin = −0.97 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	0.81077 (5)	0.01234 (5)	0.55273 (2)	0.0794 (3)
C1	1.0000	−0.2818 (8)	0.7500	0.070 (3)
H1A	1.0000	−0.3622	0.7500	0.085*
C2	0.9466 (6)	−0.2224 (5)	0.7086 (3)	0.0664 (18)
H2A	0.9108	−0.2627	0.6803	0.080*
C3	0.9455 (5)	−0.1024 (5)	0.7085 (2)	0.0484 (13)
C4	1.0000	−0.0408 (7)	0.7500	0.0429 (17)
C5	1.0000	0.0907 (7)	0.7500	0.0461 (18)
C6	1.0860 (4)	0.1536 (5)	0.7259 (2)	0.0473 (13)
C7	1.0835 (5)	0.2719 (6)	0.7253 (3)	0.0659 (17)
H7A	1.1395	0.3122	0.7077	0.079*
C8	1.0000	0.3321 (8)	0.7500	0.083 (3)
H8A	1.0000	0.4125	0.7500	0.099*
C9	0.8803 (6)	−0.0437 (5)	0.6624 (3)	0.0556 (15)
C10	1.1845 (5)	0.0952 (6)	0.6995 (3)	0.0559 (16)
C11	0.5481 (9)	0.0452 (9)	0.5938 (4)	0.108 (3)
H11A	0.5717	−0.0003	0.6229	0.130*
C12	0.4429 (11)	0.0925 (13)	0.5920 (6)	0.145 (6)
H12A	0.3943	0.0762	0.6196	0.173*
C13	0.4064 (9)	0.1619 (13)	0.5520 (7)	0.148 (7)
H13A	0.3345	0.1953	0.5524	0.178*
C14	0.4794 (7)	0.1846 (9)	0.5079 (5)	0.107 (3)
C15	0.4506 (9)	0.2534 (11)	0.4630 (8)	0.153 (7)
H15A	0.3805	0.2907	0.4615	0.183*
C16	0.5196 (12)	0.2673 (8)	0.4225 (5)	0.132 (5)
H16A	0.4964	0.3137	0.3936	0.158*
C17	0.6320 (8)	0.2111 (6)	0.4224 (4)	0.085 (2)
C18	0.7075 (11)	0.2189 (8)	0.3815 (4)	0.111 (3)
H18A	0.6891	0.2618	0.3507	0.133*
C19	0.8068 (10)	0.1640 (8)	0.3867 (3)	0.099 (3)
H19A	0.8572	0.1669	0.3590	0.118*
C20	0.8361 (6)	0.1025 (6)	0.4333 (3)	0.0734 (19)
H20A	0.9071	0.0671	0.4363	0.088*
C21	0.6640 (5)	0.1444 (5)	0.4685 (3)	0.0574 (15)
C22	0.5854 (5)	0.1301 (6)	0.5117 (3)	0.071 (2)
N1	0.6176 (5)	0.0637 (6)	0.5541 (2)	0.0738 (16)
N2	0.7670 (4)	0.0925 (4)	0.47350 (19)	0.0550 (12)
O1	0.9113 (4)	−0.0678 (4)	0.61601 (18)	0.0740 (13)
O2	0.8007 (4)	0.0204 (4)	0.67257 (19)	0.0720 (13)
O3	1.2028 (4)	0.1158 (4)	0.65313 (19)	0.0761 (13)
O4	1.2503 (4)	0.0277 (4)	0.7283 (2)	0.0683 (12)
H4A	1.2340	0.0253	0.7612	0.082*

	U11	U22	U33	U12	U13	U23
Ag1	0.0838 (5)	0.0943 (5)	0.0584 (4)	0.0106 (3)	−0.0170 (3)	−0.0002 (3)
C1	0.095 (7)	0.047 (5)	0.070 (7)	0.000	0.005 (6)	0.000
C2	0.085 (5)	0.057 (4)	0.057 (4)	−0.012 (3)	0.001 (4)	−0.007 (3)
C3	0.051 (3)	0.046 (3)	0.048 (3)	0.002 (2)	0.001 (3)	−0.005 (3)
C4	0.037 (4)	0.049 (5)	0.043 (4)	0.000	0.005 (3)	0.000
C5	0.045 (4)	0.050 (5)	0.043 (4)	0.000	0.000 (4)	0.000
C6	0.043 (3)	0.052 (4)	0.047 (3)	−0.006 (3)	0.005 (2)	0.001 (3)
C7	0.066 (4)	0.058 (4)	0.075 (5)	−0.009 (3)	0.022 (3)	0.007 (3)
C8	0.103 (8)	0.045 (5)	0.103 (8)	0.000	0.029 (7)	0.000
C9	0.053 (4)	0.060 (4)	0.053 (4)	−0.007 (3)	−0.007 (3)	−0.004 (3)
C10	0.039 (3)	0.068 (4)	0.061 (4)	−0.007 (3)	0.010 (3)	−0.004 (3)
C11	0.091 (7)	0.133 (7)	0.105 (7)	−0.049 (6)	0.042 (6)	−0.058 (6)
C12	0.091 (10)	0.180 (15)	0.167 (13)	−0.055 (9)	0.050 (8)	−0.122 (11)
C13	0.045 (6)	0.167 (13)	0.233 (17)	−0.008 (6)	0.023 (9)	−0.141 (12)
C14	0.064 (6)	0.107 (7)	0.149 (9)	0.019 (5)	−0.018 (6)	−0.076 (7)
C15	0.069 (7)	0.115 (9)	0.27 (2)	0.030 (6)	−0.071 (9)	−0.063 (12)
C16	0.144 (11)	0.074 (6)	0.169 (12)	0.022 (7)	−0.092 (9)	−0.002 (7)
C17	0.112 (6)	0.054 (4)	0.084 (6)	−0.001 (4)	−0.039 (5)	−0.012 (4)
C18	0.200 (12)	0.072 (6)	0.057 (5)	−0.018 (6)	−0.022 (7)	0.007 (4)
C19	0.152 (9)	0.084 (6)	0.062 (6)	−0.029 (6)	0.019 (6)	−0.005 (5)
C20	0.073 (5)	0.086 (5)	0.061 (5)	−0.011 (4)	0.007 (4)	−0.015 (4)
C21	0.059 (4)	0.053 (4)	0.059 (4)	0.003 (3)	−0.016 (3)	−0.012 (3)
C22	0.044 (4)	0.077 (5)	0.091 (6)	0.001 (3)	−0.007 (4)	−0.043 (4)
N1	0.061 (4)	0.098 (5)	0.063 (4)	−0.014 (3)	0.015 (3)	−0.027 (3)
N2	0.057 (3)	0.062 (3)	0.046 (3)	0.002 (2)	0.001 (2)	−0.011 (2)
O1	0.075 (3)	0.098 (4)	0.048 (3)	0.009 (3)	−0.004 (2)	0.001 (2)
O2	0.065 (3)	0.088 (3)	0.062 (3)	0.021 (2)	−0.009 (2)	−0.003 (2)
O3	0.067 (3)	0.102 (4)	0.061 (3)	0.003 (2)	0.024 (2)	0.005 (3)
O4	0.049 (2)	0.085 (3)	0.071 (3)	0.011 (2)	0.013 (2)	0.006 (2)

Ag1—O1	2.141 (4)	C11—C12	1.352 (15)
Ag1—N2	2.220 (5)	C11—H11A	0.9300
Ag1—N1	2.350 (6)	C12—C13	1.337 (18)
C1—C2	1.369 (8)	C12—H12A	0.9300
C1—C2i	1.369 (8)	C13—C14	1.445 (17)
C1—H1A	0.9300	C13—H13A	0.9300
C2—C3	1.389 (8)	C14—C22	1.397 (11)
C2—H2A	0.9300	C14—C15	1.401 (18)
C3—C4	1.390 (7)	C15—C16	1.329 (17)
C3—C9	1.514 (8)	C15—H15A	0.9300
C4—C3i	1.390 (7)	C16—C17	1.474 (14)
C4—C5	1.521 (11)	C16—H16A	0.9300
C5—C6i	1.402 (6)	C17—C18	1.383 (12)
C5—C6	1.402 (6)	C17—C21	1.419 (10)
C6—C7	1.370 (8)	C18—C19	1.332 (13)
C6—C10	1.515 (8)	C18—H18A	0.9300
C7—C8	1.371 (8)	C19—C20	1.391 (11)
C7—H7A	0.9300	C19—H19A	0.9300
C8—C7i	1.371 (8)	C20—N2	1.320 (8)
C8—H8A	0.9300	C20—H20A	0.9300
C9—O2	1.230 (8)	C21—N2	1.353 (7)
C9—O1	1.255 (7)	C21—C22	1.457 (10)
C10—O3	1.207 (7)	C22—N1	1.346 (9)
C10—O4	1.295 (7)	O4—H4A	0.8492
C11—N1	1.326 (9)
O1—Ag1—N2	159.20 (18)	C12—C13—C14	119.6 (12)
O1—Ag1—N1	127.1 (2)	C12—C13—H13A	120.2
N2—Ag1—N1	73.7 (2)	C14—C13—H13A	120.2
C2—C1—C2i	119.7 (9)	C22—C14—C15	119.8 (11)
C2—C1—H1A	120.1	C22—C14—C13	115.0 (12)
C2i—C1—H1A	120.1	C15—C14—C13	125.2 (11)
C1—C2—C3	120.5 (6)	C16—C15—C14	122.5 (11)
C1—C2—H2A	119.8	C16—C15—H15A	118.7
C3—C2—H2A	119.8	C14—C15—H15A	118.7
C2—C3—C4	120.5 (6)	C15—C16—C17	121.6 (11)
C2—C3—C9	117.0 (5)	C15—C16—H16A	119.2
C4—C3—C9	122.5 (5)	C17—C16—H16A	119.2
C3—C4—C3i	118.3 (7)	C18—C17—C21	118.3 (8)
C3—C4—C5	120.9 (4)	C18—C17—C16	125.2 (10)
C3i—C4—C5	120.9 (4)	C21—C17—C16	116.5 (9)
C6i—C5—C6	117.4 (7)	C19—C18—C17	119.0 (8)
C6i—C5—C4	121.3 (3)	C19—C18—H18A	120.5
C6—C5—C4	121.3 (3)	C17—C18—H18A	120.5
C7—C6—C5	120.6 (5)	C18—C19—C20	120.8 (8)
C7—C6—C10	117.2 (5)	C18—C19—H19A	119.6
C5—C6—C10	122.2 (5)	C20—C19—H19A	119.6
C6—C7—C8	121.2 (6)	N2—C20—C19	122.5 (8)
C6—C7—H7A	119.4	N2—C20—H20A	118.7
C8—C7—H7A	119.4	C19—C20—H20A	118.7
C7i—C8—C7	118.9 (9)	N2—C21—C17	121.5 (7)
C7i—C8—H8A	120.5	N2—C21—C22	118.4 (6)
C7—C8—H8A	120.5	C17—C21—C22	120.2 (7)
O2—C9—O1	125.2 (6)	N1—C22—C14	122.2 (9)
O2—C9—C3	118.7 (6)	N1—C22—C21	118.4 (6)
O1—C9—C3	116.1 (6)	C14—C22—C21	119.4 (9)
O3—C10—O4	121.5 (5)	C11—N1—C22	120.8 (8)
O3—C10—C6	119.8 (6)	C11—N1—Ag1	126.7 (7)
O4—C10—C6	118.6 (6)	C22—N1—Ag1	112.0 (4)
N1—C11—C12	120.2 (12)	C20—N2—C21	117.9 (6)
N1—C11—H11A	119.9	C20—N2—Ag1	125.6 (5)
C12—C11—H11A	119.9	C21—N2—Ag1	116.2 (4)
C13—C12—C11	122.1 (13)	C9—O1—Ag1	114.0 (4)
C13—C12—H12A	118.9	C10—O4—H4A	113.5
C11—C12—H12A	118.9

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···O2i	0.85	1.71	2.564 (7)	179

Table 1

Selected bond lengths (Å)

Ag1—O1	2.141 (4)
Ag1—N2	2.220 (5)
Ag1—N1	2.350 (6)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4A⋯O2i	0.85	1.71	2.564 (7)	179

Symmetry code: (i) .