catena-Poly[[(p-toluene-sulfonato-κO)silver(I)]-μ-1,3-bis-(pyridin-4-yl)propane-κ(2)N:N'].

In the title compound, [Ag(C(7)H(7)O(3)S)(C(13)H(14)N(2))](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-toluene-sulfonate ligand, forming a one-dimensional zigzag chain along [001]. In the crystal, weak C-H⋯O hydrogen bonds and weak Ag⋯Ag inter-actions [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 = 477.33

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.075

S = 0.94

3450 reflections

245 parameters

H-atom parameters constrained

Δρmax = 0.63 e Å−3

Δρmin = −0.55 e Å−3

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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812015218/lh5431sup1.cif

Supplementary material file. DOI: 10.1107/S1600536812015218/lh5431Isup2.cdx

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

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

[Ag(C7H7O3S)(C13H14N2)]	F(000) = 968
Mr = 477.33	Dx = 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

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

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(Fo2) + (0.032P)2 + 1.9473P] where P = (Fo2 + 2Fc2)/3
S = 0.94	(Δ/σ)max = 0.001
3450 reflections	Δρmax = 0.63 e Å−3
245 parameters	Δρmin = −0.55 e Å−3
0 restraints	Extinction correction: SHELXL
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0029 (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
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)

	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)

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

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14B···O2iv	0.97	2.56	3.533 (4)	178
C12—H12···O1i	0.93	2.58	3.332 (4)	138
C8—H8···O3v	0.93	2.46	3.305 (4)	151

Table 1

Selected bond lengths (Å)

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

Symmetry code: (i) .

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) ; (ii) ; (iii) .