catena-Poly[[bis­(μ2-4-amino­benzene­sulfonato-κ2O:O)disilver]-bis­(μ2-4,4′-bipyridine-κ2N:N′)]

Ou, G.-C.; Zhang, M.; Yuan, X.-Y.; Dai, Y.-Q.

doi:10.1107/S160053680803804X

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page m1587

doi:10.1107/S160053680803804X

Open

access

catena-Poly[[bis(μ₂-4-aminobenzenesulfonato-κ²O:O)disilver]-bis(μ₂-4,4′-bipyridine-κ²N:N′)]

Guang-Chuan Ou,^a ^* Min Zhang,^a Xian-You Yuan ^a and Yong-Qiang Dai ^a

^aDepartment of Biology and Chemistry, Hunan University of Science and Engineering, Yongzhou, Hunan 425100, People's Republic of China
^*Correspondence e-mail: ouguangchuan@yahoo.com.cn

(Received 30 September 2008; accepted 16 November 2008; online 22 November 2008)

In the title compound, [Ag₂(C₆H₆NO₃S)₂(C₁₀H₈N₂)₂]_n, the Ag^I atom is four-coordinated by two N atoms from two symmetry-related 4,4′-bipyridine (bipy) and two O atoms from two independent 4-aminobenzenesulfonate (ABS) ligands. The two inter-chain Ag^I atoms are bridged by two independent ABS ligands through weak Ag—O bonds and Ag⋯Ag attractions, forming a ladder-like chain coordination polymer [Ag₂(ABS)₂(bipy)₂]_n parallel to [001], which is further linked to generate a two-dimensional structure via N—H⋯O hydrogen-bonding interactions.

Related literature

For general background, see: Liu, Kuroda-Sowa et al. (2005 ); Liu, Liu et al. (2005 ); Feng et al. (2003 ); Wei et al. (2004 ); Dong et al. (2005 ); Bi et al. (2003 ); Ding et al. (2005 ); Yang et al. (2004 ). For related structures, see: Sampanthar & Vittal (2000 ); Tong et al. (2000 ).

Experimental

Crystal data

[Ag₂(C₆H₆NO₃S)₂(C₁₀H₈N₂)₂]
M_r = 872.46
Monoclinic, P 2₁ /n
a = 9.2105 (19) Å
b = 15.774 (3) Å
c = 11.433 (2) Å
β = 108.004 (4)°
V = 1579.8 (6) Å³
Z = 2
Mo Kα radiation
μ = 1.43 mm⁻¹
T = 173 (2) K
0.42 × 0.13 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.585, T_max = 0.847
7741 measured reflections
3375 independent reflections
2774 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.088
S = 1.11
3375 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.79 e Å⁻³
Δρ_min = −0.69 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3B⋯O2ⁱ	0.88	2.04	2.850 (5)	153
N3—H3C⋯O3ⁱⁱ	0.88	2.25	2.905 (4)	131
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) x-1, y, z.

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 2003 ); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2005 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680803804X/pv2110sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680803804X/pv2110Isup2.hkl

checkCIF report

Comment top

In the construction of inorganic–organic supramolecular complexes, the Ag^I is often a favorable candidate due to its flexible coordination modes and Ag–Ag attractions (Liu et al., 2005; Dong et al., 2005; Bi et al., 2003; Ding et al., 2005; Yang et al., 2004). Bipy (4,4'-bipyridine) and ABS (4-aminobenzenesulfonic acid) are useful building blocks because they contain bifunctional groups, which can coordinate with metal ions in various coordination modes through the oxygen atoms of sulfonic group and the nitrogen atoms of pyridyl ring (Liu et al., 2005; Feng et al., 2003; Wei et al., 2004). Therefore, we also extended these investigations to the use of the ligand ABS and obtained various framework structures. In this paper, we report the structure of the title compound, (I).

As illustrated in Fig. 1, each Ag^I atom in the title compound is four-coordinated by two nitrogen atoms from bipy (Ag1—N1 = 2.187 (3) Å, Ag1—N2 = 2.179 (3) Å) and two oxygen atoms from two independent ABS (Ag1—O1 = 2.572 (2) Å and Ag1—O1# = 2.654 (2) Å, # 1 - x, -y, 1 - z). These coordination modes are different from those found in structures similar to (I), wherein both oxygen atoms of acetic acid are linked to Ag atoms (Sampanthar & Vittal, 2000; Tong et al., 2000). The two inter-chain Ag^I atoms are bridged by two independent ABS ligands through week Ag—O bonds and Ag–Ag attractions (Ag1–Ag1# = 3.903 Å, # 1 - x, -y, 1 - z), forming a one-dimensional ladder-like chain coordination polymer [Ag₂(bipy)₂(ABS)₂]_n with periodical distance of 11.43 Å, which is further linked to generate a two-dimensional structure via hydrogen-bonding interactions with an average O–O distance of 2.877 Å (Fig. 2).

Related literature top

For general background, see: Liu, Kuroda-Sowa et al., 2005; Liu, Liu et al. (2005); Feng et al. (2003); Wei et al. (2004); Dong et al. (2005); Bi et al. (2003); Ding et al. (2005); Yang et al. (2004). For related structures, see: Sampanthar & Vittal (2000); Tong et al. (2000).

Experimental top

To a mixture of bipy (0.032 g, 0.2 mmol), ABS (0.017 g, 0.1 mmol) and Ag₂O (0.028 g, 0.05 mmol) in CH₃OH (10 ml) was added ammonia water resulting in a clear solution. After heating at 323 K for 0.5 h, the solution was evaporated slowly in the dark. Five days later, slightly yellow crystals were formed from the solution.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART (Bruker, 1997); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2005); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing displacement ellipsoids at the 30% probability level; H-atoms have been excluded for clarity. The symmetry codes for the generated atoms: a (1 - x, -y, 1 - z), b (1 - x, -y, 2 - z), c (x, y, 1 + z), d (x, y, -1 + z), e (1 - x, -y, -z).
	Fig. 2. A view of the packing of the title compound along b axis.

catena-Poly[[bis(µ₂-4-aminobenzenesulfonato-κ²O:O)disilver]- bis(µ₂-4,4'-bipyridine-κ²N:N')] top

Crystal data top

[Ag₂(C₆H₆NO₃S)₂(C₁₀H₈N₂)₂]	F(000) = 872
M_r = 872.46	D_x = 1.834 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2489 reflections
a = 9.2105 (19) Å	θ = 2.5–27.0°
b = 15.774 (3) Å	µ = 1.43 mm⁻¹
c = 11.433 (2) Å	T = 173 K
β = 108.004 (4)°	Prism, light-yellow
V = 1579.8 (6) Å³	0.42 × 0.13 × 0.12 mm
Z = 2

Data collection top

Bruker SMART CCD area-detector diffractometer	3375 independent reflections
Radiation source: fine-focus sealed tube	2774 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ϕ and ω scans	θ_max = 27.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.585, T_max = 0.847	k = −17→20
7741 measured reflections	l = −13→14

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.088	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.0458P)² + 0.7557P] where P = (F_o² + 2F_c²)/3
3375 reflections	(Δ/σ)_max = 0.001
217 parameters	Δρ_max = 0.79 e Å⁻³
0 restraints	Δρ_min = −0.69 e Å⁻³

Crystal data top

[Ag₂(C₆H₆NO₃S)₂(C₁₀H₈N₂)₂]	V = 1579.8 (6) Å³
M_r = 872.46	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.2105 (19) Å	µ = 1.43 mm⁻¹
b = 15.774 (3) Å	T = 173 K
c = 11.433 (2) Å	0.42 × 0.13 × 0.12 mm
β = 108.004 (4)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3375 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2774 reflections with I > 2σ(I)
T_min = 0.585, T_max = 0.847	R_int = 0.023
7741 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.088	H-atom parameters constrained
S = 1.11	Δρ_max = 0.79 e Å⁻³
3375 reflections	Δρ_min = −0.69 e Å⁻³
217 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Ag1	0.72113 (3)	0.011584 (16)	0.56851 (2)	0.02788 (10)
S1	0.43413 (9)	0.19537 (5)	0.48987 (9)	0.0333 (2)
N1	0.7468 (3)	0.01972 (15)	0.3849 (2)	0.0216 (5)
N2	0.7473 (3)	0.01021 (16)	0.7646 (2)	0.0250 (6)
C2	0.7508 (3)	0.01617 (18)	0.1402 (3)	0.0203 (6)
C12	0.1224 (3)	0.19650 (18)	0.4380 (3)	0.0236 (6)
H12A	0.1175	0.1865	0.3549	0.028*
C14	−0.0062 (3)	0.2155 (2)	0.5922 (3)	0.0274 (7)
C1	0.7521 (3)	0.01415 (18)	0.0111 (3)	0.0211 (6)
O1	0.4856 (2)	0.10869 (15)	0.5186 (2)	0.0362 (6)
C11	0.2636 (3)	0.20524 (19)	0.5282 (3)	0.0228 (6)
C15	0.1367 (4)	0.2258 (2)	0.6808 (3)	0.0299 (7)
H15A	0.1427	0.2368	0.7638	0.036*
C10	0.6969 (4)	0.0780 (2)	0.8123 (3)	0.0282 (7)
H10A	0.6607	0.1256	0.7607	0.034*
C7	0.8025 (4)	−0.0552 (2)	0.8414 (3)	0.0273 (7)
H7A	0.8388	−0.1036	0.8097	0.033*
C16	0.2681 (4)	0.2204 (2)	0.6487 (3)	0.0288 (7)
H16A	0.3641	0.2270	0.7103	0.035*
C13	−0.0112 (3)	0.2024 (2)	0.4698 (3)	0.0258 (7)
H13A	−0.1072	0.1974	0.4078	0.031*
C3	0.8647 (3)	−0.02265 (19)	0.2346 (3)	0.0240 (6)
H3A	0.9463	−0.0514	0.2171	0.029*
C6	0.6367 (3)	0.0573 (2)	0.2940 (3)	0.0249 (6)
H6A	0.5563	0.0855	0.3141	0.030*
C5	0.6351 (3)	0.0569 (2)	0.1740 (3)	0.0258 (7)
H5A	0.5547	0.0846	0.1132	0.031*
C4	0.8586 (4)	−0.01927 (19)	0.3527 (3)	0.0261 (7)
H4A	0.9379	−0.0460	0.4155	0.031*
O2	0.3940 (4)	0.2091 (3)	0.3591 (3)	0.0931 (15)
N3	−0.1373 (3)	0.2149 (2)	0.6265 (3)	0.0483 (9)
H3B	−0.1314	0.2211	0.7043	0.058*
H3C	−0.2269	0.2084	0.5705	0.058*
O3	0.5398 (3)	0.25465 (19)	0.5646 (4)	0.0858 (13)
C8	0.8091 (4)	−0.0555 (2)	0.9632 (3)	0.0260 (7)
H8	0.8518	−0.1024	1.0143	0.031*
C9	0.6953 (4)	0.0818 (2)	0.9318 (3)	0.0277 (7)
H9	0.6555	0.1304	0.9604	0.033*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.03363 (16)	0.03836 (16)	0.01360 (14)	0.00271 (10)	0.01013 (10)	0.00153 (10)
S1	0.0248 (4)	0.0333 (5)	0.0465 (5)	0.0039 (3)	0.0178 (4)	0.0092 (4)
N1	0.0276 (13)	0.0222 (13)	0.0164 (12)	−0.0020 (10)	0.0090 (10)	−0.0024 (10)
N2	0.0300 (14)	0.0297 (14)	0.0160 (13)	0.0008 (11)	0.0082 (11)	0.0003 (11)
C2	0.0287 (15)	0.0198 (14)	0.0139 (14)	−0.0011 (12)	0.0085 (12)	−0.0014 (11)
C12	0.0287 (16)	0.0210 (15)	0.0198 (15)	0.0019 (12)	0.0054 (13)	0.0011 (12)
C14	0.0216 (15)	0.0269 (16)	0.0351 (19)	0.0021 (12)	0.0109 (14)	−0.0026 (14)
C1	0.0267 (15)	0.0211 (14)	0.0153 (14)	−0.0017 (12)	0.0060 (12)	−0.0013 (11)
O1	0.0277 (12)	0.0297 (13)	0.0522 (16)	0.0044 (9)	0.0138 (11)	−0.0036 (11)
C11	0.0188 (14)	0.0234 (15)	0.0272 (16)	0.0013 (11)	0.0086 (12)	0.0005 (13)
C15	0.0338 (17)	0.0356 (18)	0.0223 (17)	−0.0021 (14)	0.0115 (14)	−0.0086 (14)
C10	0.0416 (18)	0.0236 (16)	0.0194 (16)	0.0030 (13)	0.0094 (14)	0.0033 (13)
C7	0.0338 (17)	0.0296 (17)	0.0196 (16)	0.0051 (13)	0.0099 (13)	−0.0007 (13)
C16	0.0258 (16)	0.0323 (18)	0.0235 (17)	−0.0009 (13)	0.0005 (13)	−0.0066 (13)
C13	0.0208 (15)	0.0274 (16)	0.0251 (16)	0.0004 (12)	0.0010 (13)	0.0013 (13)
C3	0.0248 (15)	0.0269 (16)	0.0198 (16)	0.0053 (12)	0.0062 (12)	−0.0004 (12)
C6	0.0266 (15)	0.0278 (16)	0.0200 (15)	0.0046 (12)	0.0071 (12)	−0.0025 (13)
C5	0.0257 (15)	0.0335 (18)	0.0175 (15)	0.0061 (13)	0.0054 (12)	0.0002 (13)
C4	0.0288 (16)	0.0270 (16)	0.0208 (16)	0.0046 (13)	0.0053 (13)	−0.0017 (13)
O2	0.064 (2)	0.163 (4)	0.070 (2)	0.054 (2)	0.0474 (19)	0.071 (3)
N3	0.0304 (16)	0.080 (2)	0.0402 (19)	0.0081 (16)	0.0189 (14)	−0.0024 (18)
O3	0.0339 (15)	0.0463 (18)	0.185 (4)	−0.0175 (14)	0.045 (2)	−0.046 (2)
C8	0.0345 (17)	0.0243 (16)	0.0193 (15)	0.0075 (13)	0.0085 (13)	0.0024 (13)
C9	0.0390 (18)	0.0246 (16)	0.0210 (16)	0.0068 (13)	0.0114 (13)	0.0010 (13)

Geometric parameters (Å, º) top

Ag1—N2	2.179 (3)	C11—C16	1.387 (4)
Ag1—N1	2.187 (3)	C15—C16	1.372 (5)
Ag1—O1	2.571 (2)	C15—H15A	0.9500
S1—O3	1.428 (3)	C10—C9	1.372 (4)
S1—O2	1.441 (3)	C10—H10A	0.9500
S1—O1	1.451 (2)	C7—C8	1.375 (4)
S1—C11	1.763 (3)	C7—H7A	0.9500
N1—C4	1.345 (4)	C16—H16A	0.9500
N1—C6	1.345 (4)	C13—H13A	0.9500
N2—C10	1.347 (4)	C3—C4	1.370 (5)
N2—C7	1.348 (4)	C3—H3A	0.9500
C2—C3	1.393 (4)	C6—C5	1.368 (4)
C2—C5	1.398 (4)	C6—H6A	0.9500
C2—C1	1.480 (4)	C5—H5A	0.9500
C12—C13	1.390 (4)	C4—H4A	0.9500
C12—C11	1.394 (4)	N3—H3B	0.8800
C12—H12A	0.9500	N3—H3C	0.8800
C14—N3	1.380 (4)	C8—C1ⁱⁱ	1.399 (4)
C14—C15	1.400 (4)	C8—H8	0.9500
C14—C13	1.401 (4)	C9—C1ⁱⁱ	1.393 (4)
C1—C9ⁱ	1.393 (4)	C9—H9	0.9500
C1—C8ⁱ	1.399 (4)

N2—Ag1—N1	167.73 (10)	N2—C10—C9	123.4 (3)
N2—Ag1—O1	92.98 (9)	N2—C10—H10A	118.3
N1—Ag1—O1	94.93 (9)	C9—C10—H10A	118.3
O3—S1—O2	115.6 (2)	N2—C7—C8	123.5 (3)
O3—S1—O1	111.53 (19)	N2—C7—H7A	118.2
O2—S1—O1	109.7 (2)	C8—C7—H7A	118.2
O3—S1—C11	106.77 (17)	C15—C16—C11	121.2 (3)
O2—S1—C11	106.38 (16)	C15—C16—H16A	119.4
O1—S1—C11	106.33 (14)	C11—C16—H16A	119.4
C4—N1—C6	116.7 (3)	C12—C13—C14	120.8 (3)
C4—N1—Ag1	123.7 (2)	C12—C13—H13A	119.6
C6—N1—Ag1	119.2 (2)	C14—C13—H13A	119.6
C10—N2—C7	116.8 (3)	C4—C3—C2	119.8 (3)
C10—N2—Ag1	117.8 (2)	C4—C3—H3A	120.1
C7—N2—Ag1	125.3 (2)	C2—C3—H3A	120.1
C3—C2—C5	116.4 (3)	N1—C6—C5	123.0 (3)
C3—C2—C1	121.8 (3)	N1—C6—H6A	118.5
C5—C2—C1	121.8 (3)	C5—C6—H6A	118.5
C13—C12—C11	119.9 (3)	C6—C5—C2	120.4 (3)
C13—C12—H12A	120.0	C6—C5—H5A	119.8
C11—C12—H12A	120.0	C2—C5—H5A	119.8
N3—C14—C15	120.3 (3)	N1—C4—C3	123.8 (3)
N3—C14—C13	121.4 (3)	N1—C4—H4A	118.1
C15—C14—C13	118.2 (3)	C3—C4—H4A	118.1
C9ⁱ—C1—C8ⁱ	117.2 (3)	C14—N3—H3B	120.0
C9ⁱ—C1—C2	121.0 (3)	C14—N3—H3C	120.0
C8ⁱ—C1—C2	121.8 (3)	H3B—N3—H3C	120.0
S1—O1—Ag1	143.69 (14)	C7—C8—C1ⁱⁱ	119.3 (3)
C16—C11—C12	119.1 (3)	C7—C8—H8	120.4
C16—C11—S1	120.5 (2)	C1ⁱⁱ—C8—H8	120.4
C12—C11—S1	120.4 (2)	C10—C9—C1ⁱⁱ	119.8 (3)
C16—C15—C14	120.6 (3)	C10—C9—H9	120.1
C16—C15—H15A	119.7	C1ⁱⁱ—C9—H9	120.1
C14—C15—H15A	119.7

N2—Ag1—N1—C4	49.1 (6)	N3—C14—C15—C16	175.3 (3)
O1—Ag1—N1—C4	179.0 (2)	C13—C14—C15—C16	−2.2 (5)
N2—Ag1—N1—C6	−138.8 (4)	C7—N2—C10—C9	−2.1 (5)
O1—Ag1—N1—C6	−8.9 (2)	Ag1—N2—C10—C9	174.4 (3)
N1—Ag1—N2—C10	102.1 (5)	C10—N2—C7—C8	0.1 (5)
O1—Ag1—N2—C10	−28.0 (2)	Ag1—N2—C7—C8	−176.1 (2)
N1—Ag1—N2—C7	−81.8 (5)	C14—C15—C16—C11	0.6 (5)
O1—Ag1—N2—C7	148.2 (3)	C12—C11—C16—C15	0.8 (5)
C3—C2—C1—C9ⁱ	−147.0 (3)	S1—C11—C16—C15	−178.2 (3)
C5—C2—C1—C9ⁱ	33.1 (4)	C11—C12—C13—C14	−1.2 (5)
C3—C2—C1—C8ⁱ	33.5 (4)	N3—C14—C13—C12	−174.9 (3)
C5—C2—C1—C8ⁱ	−146.4 (3)	C15—C14—C13—C12	2.5 (5)
O3—S1—O1—Ag1	−41.8 (3)	C5—C2—C3—C4	0.0 (4)
O2—S1—O1—Ag1	87.6 (3)	C1—C2—C3—C4	−179.9 (3)
C11—S1—O1—Ag1	−157.8 (2)	C4—N1—C6—C5	0.1 (4)
N2—Ag1—O1—S1	102.2 (3)	Ag1—N1—C6—C5	−172.5 (2)
N1—Ag1—O1—S1	−68.4 (3)	N1—C6—C5—C2	0.1 (5)
C13—C12—C11—C16	−0.5 (5)	C3—C2—C5—C6	−0.2 (4)
C13—C12—C11—S1	178.4 (2)	C1—C2—C5—C6	179.7 (3)
O3—S1—C11—C16	−37.0 (3)	C6—N1—C4—C3	−0.3 (5)
O2—S1—C11—C16	−160.9 (3)	Ag1—N1—C4—C3	172.0 (2)
O1—S1—C11—C16	82.2 (3)	C2—C3—C4—N1	0.3 (5)
O3—S1—C11—C12	144.1 (3)	N2—C7—C8—C1ⁱⁱ	1.9 (5)
O2—S1—C11—C12	20.2 (3)	N2—C10—C9—C1ⁱⁱ	2.0 (5)
O1—S1—C11—C12	−96.7 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3B···O2ⁱⁱⁱ	0.88	2.04	2.850 (5)	153
N3—H3C···O3^iv	0.88	2.25	2.905 (4)	131

Symmetry codes: (iii) x−1/2, −y+1/2, z+1/2; (iv) x−1, y, z.

Experimental details

Crystal data
Chemical formula	[Ag₂(C₆H₆NO₃S)₂(C₁₀H₈N₂)₂]
M_r	872.46
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	173
a, b, c (Å)	9.2105 (19), 15.774 (3), 11.433 (2)
β (°)	108.004 (4)
V (Å³)	1579.8 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.43
Crystal size (mm)	0.42 × 0.13 × 0.12

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.585, 0.847
No. of measured, independent and observed [I > 2σ(I)] reflections	7741, 3375, 2774
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.088, 1.11
No. of reflections	3375
No. of parameters	217
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.79, −0.69

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2005).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3B···O2ⁱ	0.88	2.04	2.850 (5)	153
N3—H3C···O3ⁱⁱ	0.88	2.25	2.905 (4)	131

Symmetry codes: (i) x−1/2, −y+1/2, z+1/2; (ii) x−1, y, z.

Acknowledgements

The authors thank the Key Subject Construction Project of Hunan Province (grant No. 2006-180), the Scientific Research Project of the Hunan Provincial Finance Bureau and Education Department (grant No. 08C366), and the Foundation for University Key Teachers of the Education Department of Hunan Province for supporting this study.

References

Bi, W. H., Cao, R., Sun, D. F., Yuan, D. Q., Li, X. & Hong, M. C. (2003). Inorg. Chem. Commun. 6, 1426–1428. Web of Science CSD CrossRef CAS Google Scholar
Brandenburg, K. (2005). DIAMOND. Crystal Impact, Bonn, Germany. Google Scholar
Bruker (1997). SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2003). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ding, B., Yi, L., Liu, Y., Cheng, P., Dong, Y. B. & Ma, J. P. (2005). Inorg. Chem. Commun. 8, 38–40. Web of Science CSD CrossRef CAS Google Scholar
Dong, Y. B., Geng, Y., Ma, J. P. & Huang, R. Q. (2005). Inorg. Chem. 44, 1693–1703. Web of Science CSD CrossRef PubMed CAS Google Scholar
Feng, L. Y., Wang, Y. H., Hu, C. W., Li, Y. G. & Wang, E. B. (2003). J. Mol. Struct. 650, 115–122. Web of Science CSD CrossRef CAS Google Scholar
Liu, S. Q., Kuroda-Sowa, T., Konaka, H., Suenaga, Y., Maekawa, M., Mizutani, T., Ning, G. L. & Munakata, M. (2005). Inorg. Chem. 44, 1031–1036. Web of Science CSD CrossRef PubMed CAS Google Scholar
Liu, Z., Liu, P., Chen, Y., Wang, J. & Huang, M. H. (2005). New J. Chem. 29, 474–478. Web of Science CSD CrossRef CAS Google Scholar
Sampanthar, J. T. & Vittal, J. J. (2000). Cryst. Eng. 3, 117–120. CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tong, M. L., Chen, X. M. & Seik, W. N. (2000). Inorg. Chem. Commun. 3, 436–438. Web of Science CSD CrossRef CAS Google Scholar
Wei, Q., Nieuwenhuyzen, M., Meunier, F., Hardacre, C. & James, S. L. (2004). J. Chem. Soc. Dalton Trans., pp. 1807–1811. Google Scholar
Yang, J. H., Zheng, S. L., Yu, X. L. & Chen, X. M. (2004). Cryst. Growth Des. 4, 831–836. Web of Science CSD CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.