catena-Poly[[(p-toluene­sulfonato-κO)silver(I)]-μ-1,3-bis­(pyridin-4-yl)propane-κ2N:N′]

Ma, F.; Wei, D.-B.; Cao, Z.-M.

doi:10.1107/S1600536812015218

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Pages m611-m612

doi:10.1107/S1600536812015218

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catena-Poly[[(p-toluenesulfonato-κO)silver(I)]-μ-1,3-bis(pyridin-4-yl)propane-κ²N:N′]

Feng Ma,^a ^* Dai-Bao Wei ^a and Zhi-Min Cao ^a

^aShandong Polytechnic University, School of Chemistry and Pharmaceutical Engineering, Jinan 250353, People's Republic of China
^*Correspondence e-mail: mafengch@163.com

(Received 4 March 2012; accepted 6 April 2012; online 18 April 2012)

In the title compound, [Ag(C₇H₇O₃S)(C₁₃H₁₄N₂)]_n, the Ag^I ion is coordinated in a T-shape by two N atoms from two symmetry-related 1,3-bis(pyridin-4-yl)propane ligands and one O atom from a p-toluenesulfonate ligand, forming a one-dimensional zigzag chain along [001]. In the crystal, weak C—H⋯O hydrogen bonds and weak Ag⋯Ag interactions [3.2628 (5) Å] are observed.

Related literature

For potential applications of compounds with metal-organic framework structures, see: Horike et al. (2008 ); Liu et al. (2010 ); Lu et al. (2006 ); Li et al. (1999 ). For coordination polymers of 1,3-bis(pyridin-4-yl)propane (bpp), see: Carlucci et al. (2002 ). For mixed ligands of aromatic or aliphatic carboxylates and bpp, see: Yang et al. (2009 ); Jin et al. (2009 ); Zhang et al. (2009 ); Luo et al. (2011 ). For silver(I) sulfonate complexes, see: Wu et al. (2011 ); Smith et al. (1998 ) For similar systems with Ag⋯Ag interactions, see: Li et al. (2005 ). For a similar synthetic procedure, see: Li et al. (2006 ).

Experimental

Crystal data

[Ag(C₇H₇O₃S)(C₁₃H₁₄N₂)]
M_r = 477.33
Monoclinic, P 2₁ /n
a = 10.8061 (3) Å
b = 9.9466 (3) Å
c = 18.4288 (5) Å
β = 98.230 (3)°
V = 1960.40 (10) Å³
Z = 4
Mo Kα radiation
μ = 1.16 mm⁻¹
T = 293 K
0.52 × 0.47 × 0.36 mm

Data collection

Agilent Xcalibur Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.553, T_max = 0.659
11169 measured reflections
3450 independent reflections
2834 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.075
S = 0.94
3450 reflections
245 parameters
H-atom parameters constrained
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.55 e Å⁻³

Table 1
Selected bond lengths (Å)

N1—Ag1ⁱ	2.155 (2)
N2—Ag1	2.162 (2)
O3—Ag1	2.645 (2)
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14B⋯O2ⁱⁱ	0.97	2.56	3.533 (4)	178
C12—H12⋯O1ⁱ	0.93	2.58	3.332 (4)	138
C8—H8⋯O3ⁱⁱⁱ	0.93	2.46	3.305 (4)	151
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{5\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg & Putz, 2004 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812015218/lh5431sup1.cif

Supporting information file. DOI: 10.1107/S1600536812015218/lh5431Isup2.cdx

Structure factors: contains datablock I. DOI: 10.1107/S1600536812015218/lh5431Isup3.hkl

checkCIF report

Comment top

The design and synthesis of metal-organic frameworks (MOFs) have attracted considerable attention in recent years,not only for their intriguing structural diversity, but also because of their potential applications in the area of catalysis (Horike et al., 2008), ion exchange (Liu et al., 2010), magnetism, photochemistry (Lu et al., 2006), and porous materials (Li et al., 1999).

The reactions of silver salts with 1,3-bis(pyridin-4-yl)propane (bpp) have already afforded intresting coordination polymers with distinct structural motifs (Carlucci et al., 2002). Moreover, the combination of Ag cations with mixed ligands of aromatic (Yang et al., 2009; Jin et al., 2009; Zhang et al., 2009) or aliphatic (Luo et al., 2011) carboxylates and bpp can allow the formation of MOFs possessing fascinating architectures and novel topologies. In terms of silver(I) sulfonate complexes, many nitrogen-based secondary ligands such as pyrazine (Pyr) (Li et al., 2005), hexamethylenetetramine (hmt) (Wu et al., 2011), pyridine (py) (Smith et al., 1998) and their analogues or derivatives were exploited as secondary ligands to synthesize new metal organic frameworks. Here we report a novel one-dimensional polymer [Ag(C₇H₇O₃S)(C₁₃H₁₄N₂)]_n assembled by mixed ligands of p-toluenesulfonate and bpp with silver nitrate.

The asymmetric unit of the title compound (I) and symmetry related atoms are shown in Fig. 1. The Ag^I cation is coordinated by two N atoms from two symmetry related bpp ligands one O atom from one p-toluenesulfonate ligand. The Ag—O and Ag—N bonds are comparable to those in the literature (Li et al., 2005). As shown in Fig. 2, there are weak Ag···Ag interactions (3.2628 (5)Å) which are shorter than the sum van der Waals radii for Ag···Ag [3.40Å]. Compound (I) is a one-dimensional coordination polymer formed by bpp ligands and Ag cations, with tos ligands as the side chains in which bpp ligands exhibit the TG (Carlucci et al., 2002) conformation and the N···N separation is 8.6746 (2)Å. The weak Ag ···Ag interactions bridge the undulating 1-D chains to form 2-D layers (Fig .2), which are further linked into a three-dimensional network via weak C—H···O hydrogen bonds.

Related literature top

For potential applications of metal-organic frameworks, see: Horike et al. (2008); Liu et al. (2010); Lu et al. (2006); Li et al. (1999). For coordination polymers of 1,3-bis(pyridin-4-yl)propane (bpp), see: Carlucci et al. (2002). For mixed ligands of aromatic or aliphatic carboxylates and bpp, see: Yang et al. (2009); Jin et al. (2009); Zhang et al. (2009); Luo et al. (2011). For silver(I) sulfonate complexes, see: Wu et al. (2011); Smith et al. (1998) For similar systems with Ag···Ag interactions, see: Li et al. (2005). For a similar synthetic procedure, see: Li et al. (2006).

Experimental top

A solution of bpp and tos in 8 ml methanol and 2 ml water was slowly added to a solution of AgNO₃(0.1668 g) in 8 ml water. A white suspension formed immediately. An aqueous NH₃ solution (25%) was dropped into the mixture to give a clear solution. The resultant colorless filtrate (pH=9.0) was allowed to evaporate slowly at room temperature. After one week, colorless block crystals were obtained in 52.87% yield (based on Ag). Elemental analysis for (I) (%): calculated: C 50.3, H 4.4, N 5.9, O 10.1, S 6.7. Found C49.94, H 4.452, N 5.969, O 10.123, S 7.013.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg & Putz, 2004); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), with 50% probability displacement ellipsoids for non-H atoms. Atoms labeled with capital "A" were generated through the symmetry operation (x - 1/2, -y + 3/2, z + 1/2).
	Fig. 2. Part of the crystal structure. Tos and bpp ligands have been simplified by replacing molecules with their centroids (dummy atoms). Dashed lines indicate weak Ag···Ag interactions.

catena-Poly[[(p-toluenesulfonato-κO)silver(I)]- µ-1,3-bis(pyridin-4-yl)propane-κ²N:N'] top

Crystal data top

[Ag(C₇H₇O₃S)(C₁₃H₁₄N₂)]	F(000) = 968
M_r = 477.33	D_x = 1.617 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2yn	Cell parameters from 4048 reflections
a = 10.8061 (3) Å	θ = 2.8–28.9°
b = 9.9466 (3) Å	µ = 1.16 mm⁻¹
c = 18.4288 (5) Å	T = 293 K
β = 98.230 (3)°	Block, colorless
V = 1960.40 (10) Å³	0.52 × 0.47 × 0.36 mm
Z = 4

Data collection top

Agilent Xcalibur Eos Gemini diffractometer	3450 independent reflections
Radiation source: Enhance (Mo) X-ray Source'	2834 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.8°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	h = −12→12
T_min = 0.553, T_max = 0.659	k = −11→11
11169 measured reflections	l = −21→21

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.030	H-atom parameters constrained
wR(F²) = 0.075	w = 1/[σ²(F_o²) + (0.032P)² + 1.9473P] where P = (F_o² + 2F_c²)/3
S = 0.94	(Δ/σ)_max = 0.001
3450 reflections	Δρ_max = 0.63 e Å⁻³
245 parameters	Δρ_min = −0.55 e Å⁻³
0 restraints	Extinction correction: SHELXL
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0029 (3)

Crystal data top

[Ag(C₇H₇O₃S)(C₁₃H₁₄N₂)]	V = 1960.40 (10) Å³
M_r = 477.33	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.8061 (3) Å	µ = 1.16 mm⁻¹
b = 9.9466 (3) Å	T = 293 K
c = 18.4288 (5) Å	0.52 × 0.47 × 0.36 mm
β = 98.230 (3)°

Data collection top

Agilent Xcalibur Eos Gemini diffractometer	3450 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	2834 reflections with I > 2σ(I)
T_min = 0.553, T_max = 0.659	R_int = 0.030
11169 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.075	H-atom parameters constrained
S = 0.94	Δρ_max = 0.63 e Å⁻³
3450 reflections	Δρ_min = −0.55 e Å⁻³
245 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
C1	0.6485 (3)	0.3186 (3)	0.37306 (16)	0.0409 (7)
C2	0.5674 (3)	0.2730 (3)	0.41963 (17)	0.0461 (8)
H2	0.5350	0.3328	0.4508	0.055*
C3	0.5348 (3)	0.1389 (4)	0.4196 (2)	0.0555 (9)
H3	0.4799	0.1099	0.4509	0.067*
C4	0.5814 (3)	0.0464 (4)	0.3743 (2)	0.0560 (9)
C5	0.6608 (3)	0.0938 (4)	0.3271 (2)	0.0594 (10)
H5	0.6920	0.0341	0.2953	0.071*
C6	0.6943 (3)	0.2273 (4)	0.32633 (18)	0.0503 (8)
H6	0.7479	0.2566	0.2944	0.060*
C7	0.5484 (4)	−0.1011 (4)	0.3759 (3)	0.0888 (14)
H7A	0.5897	−0.1488	0.3410	0.133*
H7B	0.4596	−0.1117	0.3637	0.133*
H7C	0.5750	−0.1364	0.4241	0.133*
C8	1.4014 (3)	1.0844 (3)	0.16123 (17)	0.0428 (8)
H8	1.4868	1.0709	0.1622	0.051*
C9	1.3610 (3)	1.1564 (3)	0.21756 (16)	0.0397 (7)
H9	1.4190	1.1919	0.2548	0.048*
C10	1.2347 (3)	1.1757 (3)	0.21868 (15)	0.0341 (7)
C11	1.1536 (3)	1.1223 (3)	0.16073 (16)	0.0367 (7)
H11	1.0678	1.1325	0.1593	0.044*
C12	1.1999 (3)	1.0545 (3)	0.10545 (17)	0.0399 (7)
H12	1.1438	1.0216	0.0665	0.048*
C13	1.1866 (3)	1.2496 (3)	0.28054 (17)	0.0463 (8)
H13A	1.1419	1.3292	0.2610	0.056*
H13B	1.2573	1.2789	0.3155	0.056*
C14	1.0998 (3)	1.1642 (3)	0.32062 (17)	0.0482 (8)
H14A	1.0670	1.2188	0.3571	0.058*
H14B	1.0297	1.1331	0.2858	0.058*
C15	1.1673 (3)	1.0460 (4)	0.3572 (2)	0.0637 (10)
H15A	1.2369	1.0792	0.3916	0.076*
H15B	1.2021	0.9947	0.3201	0.076*
C16	1.0919 (3)	0.9508 (3)	0.39783 (17)	0.0437 (7)
C17	0.9734 (3)	0.9066 (3)	0.36888 (18)	0.0476 (8)
H17	0.9342	0.9404	0.3244	0.057*
H18	0.8344	0.7824	0.3862	0.057*
H19	1.1140	0.7734	0.5447	0.057*
C18	0.9136 (3)	0.8116 (3)	0.40651 (17)	0.0444 (8)
C19	1.0775 (3)	0.8061 (3)	0.49934 (17)	0.0488 (8)
C20	1.1415 (3)	0.8990 (3)	0.46477 (18)	0.0496 (8)
H20	1.2198	0.9276	0.4869	0.060*
N1	1.3229 (2)	1.0335 (2)	0.10532 (13)	0.0381 (6)
N2	0.9650 (2)	0.7598 (2)	0.47099 (13)	0.0405 (6)
O1	0.6460 (2)	0.5548 (2)	0.43292 (12)	0.0563 (6)
O2	0.6561 (2)	0.5423 (3)	0.30278 (13)	0.0676 (7)
O3	0.8348 (2)	0.4792 (2)	0.39088 (14)	0.0605 (6)
S1	0.69972 (7)	0.48821 (8)	0.37467 (4)	0.0449 (2)
Ag1	0.88538 (2)	0.59100 (3)	0.521998 (14)	0.05157 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0369 (16)	0.0487 (19)	0.0340 (16)	−0.0031 (14)	−0.0054 (13)	0.0006 (15)
C2	0.0455 (18)	0.0487 (19)	0.0433 (19)	−0.0037 (15)	0.0037 (15)	−0.0019 (16)
C3	0.050 (2)	0.059 (2)	0.057 (2)	−0.0110 (17)	0.0033 (17)	0.0091 (19)
C4	0.050 (2)	0.053 (2)	0.060 (2)	−0.0068 (17)	−0.0107 (18)	−0.0034 (19)
C5	0.054 (2)	0.062 (2)	0.058 (2)	0.0060 (18)	−0.0060 (18)	−0.0189 (19)
C6	0.0407 (18)	0.063 (2)	0.0458 (19)	−0.0025 (16)	0.0026 (15)	−0.0042 (17)
C7	0.097 (3)	0.056 (3)	0.110 (4)	−0.018 (2)	0.003 (3)	−0.011 (2)
C8	0.0400 (17)	0.0460 (18)	0.0442 (19)	0.0039 (14)	0.0117 (15)	0.0086 (15)
C9	0.0445 (18)	0.0393 (17)	0.0344 (16)	−0.0052 (14)	0.0030 (14)	0.0018 (14)
C10	0.0501 (18)	0.0226 (14)	0.0316 (15)	−0.0035 (13)	0.0127 (13)	0.0041 (12)
C11	0.0380 (16)	0.0343 (16)	0.0388 (17)	0.0026 (13)	0.0089 (14)	0.0025 (13)
C12	0.0430 (18)	0.0404 (17)	0.0356 (17)	−0.0005 (14)	0.0039 (13)	−0.0004 (14)
C13	0.065 (2)	0.0344 (17)	0.0440 (18)	−0.0016 (15)	0.0219 (16)	−0.0040 (15)
C14	0.065 (2)	0.0439 (19)	0.0401 (18)	−0.0010 (16)	0.0228 (16)	−0.0050 (15)
C15	0.053 (2)	0.074 (3)	0.066 (2)	−0.0001 (19)	0.0129 (18)	0.026 (2)
C16	0.0435 (18)	0.0434 (18)	0.0454 (19)	−0.0012 (15)	0.0108 (15)	0.0054 (15)
C17	0.052 (2)	0.050 (2)	0.0389 (18)	0.0011 (16)	0.0008 (15)	0.0124 (15)
C18	0.0397 (17)	0.0474 (19)	0.0441 (19)	−0.0037 (15)	−0.0006 (14)	0.0012 (16)
C19	0.057 (2)	0.053 (2)	0.0336 (17)	−0.0044 (17)	−0.0048 (15)	0.0093 (16)
C20	0.0428 (18)	0.056 (2)	0.047 (2)	−0.0088 (16)	−0.0048 (15)	0.0068 (16)
N1	0.0487 (15)	0.0344 (13)	0.0325 (14)	0.0042 (12)	0.0108 (12)	0.0028 (11)
N2	0.0493 (15)	0.0390 (14)	0.0334 (14)	−0.0046 (12)	0.0064 (12)	0.0024 (12)
O1	0.0720 (16)	0.0508 (14)	0.0460 (14)	−0.0014 (12)	0.0079 (12)	−0.0029 (11)
O2	0.0875 (18)	0.0722 (17)	0.0398 (14)	−0.0038 (14)	−0.0025 (12)	0.0167 (13)
O3	0.0428 (13)	0.0628 (15)	0.0735 (17)	−0.0153 (11)	0.0002 (12)	0.0014 (14)
S1	0.0475 (5)	0.0484 (5)	0.0371 (4)	−0.0078 (4)	0.0002 (3)	0.0058 (4)
Ag1	0.0679 (2)	0.04608 (18)	0.04440 (18)	−0.00999 (12)	0.02079 (13)	0.00570 (12)

Geometric parameters (Å, º) top

C1—C2	1.388 (4)	C13—H13A	0.9700
C1—C6	1.390 (4)	C13—H13B	0.9700
C1—S1	1.775 (3)	C14—C15	1.493 (5)
C2—C3	1.379 (5)	C14—H14A	0.9700
C2—H2	0.9300	C14—H14B	0.9700
C3—C4	1.385 (5)	C15—C16	1.515 (4)
C3—H3	0.9300	C15—H15A	0.9700
C4—C5	1.389 (5)	C15—H15B	0.9700
C4—C7	1.511 (5)	C16—C20	1.373 (4)
C5—C6	1.377 (5)	C16—C17	1.387 (4)
C5—H5	0.9300	C17—C18	1.385 (4)
C6—H6	0.9300	C17—H17	0.9300
C7—H7A	0.9600	C18—N2	1.341 (4)
C7—H7B	0.9600	C18—H18	0.9295
C7—H7C	0.9600	C19—N2	1.334 (4)
C8—N1	1.338 (4)	C19—C20	1.365 (4)
C8—C9	1.382 (4)	C19—H19	0.9301
C8—H8	0.9300	C20—H20	0.9300
C9—C10	1.381 (4)	N1—Ag1ⁱ	2.155 (2)
C9—H9	0.9300	N2—Ag1	2.162 (2)
C10—C11	1.386 (4)	O1—S1	1.451 (2)
C10—C13	1.510 (4)	O2—S1	1.445 (2)
C11—C12	1.374 (4)	O3—S1	1.451 (2)
C11—H11	0.9300	O3—Ag1	2.645 (2)
C12—N1	1.346 (4)	Ag1—N1ⁱⁱ	2.155 (2)
C12—H12	0.9300	Ag1—Ag1ⁱⁱⁱ	3.2628 (5)
C13—C14	1.532 (4)

C2—C1—C6	118.8 (3)	C15—C14—C13	111.2 (3)
C2—C1—S1	121.6 (2)	C15—C14—H14A	109.4
C6—C1—S1	119.5 (2)	C13—C14—H14A	109.4
C3—C2—C1	120.0 (3)	C15—C14—H14B	109.4
C3—C2—H2	120.0	C13—C14—H14B	109.4
C1—C2—H2	120.0	H14A—C14—H14B	108.0
C2—C3—C4	121.9 (3)	C14—C15—C16	116.9 (3)
C2—C3—H3	119.1	C14—C15—H15A	108.1
C4—C3—H3	119.1	C16—C15—H15A	108.1
C3—C4—C5	117.5 (3)	C14—C15—H15B	108.1
C3—C4—C7	121.8 (4)	C16—C15—H15B	108.1
C5—C4—C7	120.7 (4)	H15A—C15—H15B	107.3
C6—C5—C4	121.4 (3)	C20—C16—C17	116.5 (3)
C6—C5—H5	119.3	C20—C16—C15	120.7 (3)
C4—C5—H5	119.3	C17—C16—C15	122.7 (3)
C5—C6—C1	120.4 (3)	C18—C17—C16	119.7 (3)
C5—C6—H6	119.8	C18—C17—H17	120.2
C1—C6—H6	119.8	C16—C17—H17	120.2
C4—C7—H7A	109.5	N2—C18—C17	122.8 (3)
C4—C7—H7B	109.5	N2—C18—H18	118.5
H7A—C7—H7B	109.5	C17—C18—H18	118.7
C4—C7—H7C	109.5	N2—C19—C20	123.0 (3)
H7A—C7—H7C	109.5	N2—C19—H19	118.5
H7B—C7—H7C	109.5	C20—C19—H19	118.5
N1—C8—C9	122.7 (3)	C19—C20—C16	121.0 (3)
N1—C8—H8	118.6	C19—C20—H20	119.5
C9—C8—H8	118.6	C16—C20—H20	119.5
C10—C9—C8	120.1 (3)	C8—N1—C12	117.3 (3)
C10—C9—H9	119.9	C8—N1—Ag1ⁱ	122.5 (2)
C8—C9—H9	119.9	C12—N1—Ag1ⁱ	120.1 (2)
C9—C10—C11	116.9 (3)	C19—N2—C18	117.0 (3)
C9—C10—C13	121.8 (3)	C19—N2—Ag1	119.6 (2)
C11—C10—C13	121.3 (3)	C18—N2—Ag1	122.9 (2)
C12—C11—C10	120.1 (3)	O2—S1—O3	113.49 (15)
C12—C11—H11	119.9	O2—S1—O1	113.29 (15)
C10—C11—H11	119.9	O3—S1—O1	111.93 (15)
N1—C12—C11	122.8 (3)	O2—S1—C1	106.18 (14)
N1—C12—H12	118.6	O3—S1—C1	104.30 (14)
C11—C12—H12	118.6	O1—S1—C1	106.81 (14)
C10—C13—C14	113.2 (2)	N1ⁱⁱ—Ag1—N2	160.18 (9)
C10—C13—H13A	108.9	N1ⁱⁱ—Ag1—Ag1ⁱⁱⁱ	100.65 (7)
C14—C13—H13A	108.9	N2—Ag1—Ag1ⁱⁱⁱ	87.67 (6)
C10—C13—H13B	108.9	N1ⁱⁱ—Ag1—O3	111.38 (8)
C14—C13—H13B	108.9	N2—Ag1—O3	88.42 (8)
H13A—C13—H13B	107.7

Symmetry codes: (i) x+1/2, −y+3/2, z−1/2; (ii) x−1/2, −y+3/2, z+1/2; (iii) −x+2, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14B···O2^iv	0.97	2.56	3.533 (4)	178
C12—H12···O1ⁱ	0.93	2.58	3.332 (4)	138
C8—H8···O3^v	0.93	2.46	3.305 (4)	151

Symmetry codes: (i) x+1/2, −y+3/2, z−1/2; (iv) −x+3/2, y+1/2, −z+1/2; (v) −x+5/2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Ag(C₇H₇O₃S)(C₁₃H₁₄N₂)]
M_r	477.33
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	10.8061 (3), 9.9466 (3), 18.4288 (5)
β (°)	98.230 (3)
V (Å³)	1960.40 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.16
Crystal size (mm)	0.52 × 0.47 × 0.36

Data collection
Diffractometer	Agilent Xcalibur Eos Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.553, 0.659
No. of measured, independent and observed [I > 2σ(I)] reflections	11169, 3450, 2834
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.075, 0.94
No. of reflections	3450
No. of parameters	245
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.63, −0.55

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg & Putz, 2004).

Selected bond lengths (Å) top

N1—Ag1ⁱ	2.155 (2)	O3—Ag1	2.645 (2)
N2—Ag1	2.162 (2)

Symmetry code: (i) x+1/2, −y+3/2, z−1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14B···O2ⁱⁱ	0.97	2.56	3.533 (4)	177.6
C12—H12···O1ⁱ	0.93	2.58	3.332 (4)	138.3
C8—H8···O3ⁱⁱⁱ	0.93	2.46	3.305 (4)	151.4

Symmetry codes: (i) x+1/2, −y+3/2, z−1/2; (ii) −x+3/2, y+1/2, −z+1/2; (iii) −x+5/2, y+1/2, −z+1/2.

Acknowledgements

The authors are grateful for financial support from the Science and Technology Development Plan of Shandong Province (grant No. 2010 G0020324), the University Independent Innovation Program of Jinan (grant No. 201004049) and the Special Funds for Postdoctoral Innovative Projects of Shandong Province (grant No. 200903051).

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