Structure and electrical properties of a one-dimensional polymeric silver thio­saccharinate complex with argentophilic inter­actions

Dennehy, M.; Amo-Ochoa, P.; Freire, E.; Suárez, S.; Halac, E.; Baggio, R.

doi:10.1107/S2053229618000128

Structure and electrical properties of a one-dimensional polymeric silver thiosaccharinate complex with argentophilic interactions

M. Dennehy, P. Amo-Ochoa, E. Freire, S. Suárez, E. Halac and R. Baggio

Among the potential applications of coordination polymers, electrical conductivity ranks high in technological interest. We report the synthesis, crystal structure and spectroscopic analysis of an Ag^I–thiosaccharinate one-dimensional coordination polymer {systematic name: catena-poly[[[aquatetrakis(μ₃-1,1-dioxo-1,2-benzisothiazole-3-thiolato-κ³N:S³:S³)tetrasilver(I)]-μ₂-4,4′-(propane-1,3-diyl)dipyridine-κ²N:N′] dimethyl sulfoxide hemisolvate]}, {[Ag₄(C₇H₄NO₂S₂)₄(C₁₃H₁₄N₂)(H₂O)]·0.5C₂H₆OS}_n, with the 4,4′-(propane-1,3-diyl)dipyridine ligand acting as a spacer. A relevant feature of the structure is the presence of an unusually short Ag

Ag distance of 2.8306 (9) Å, well within the range of argentophilic interactions, confirmed experimentally as such by a Raman study on the low-frequency spectrum, and corroborated theoretically by an Atoms in Molecules (AIM) analysis of the calculated electron density. Electrical conductivity measurements show that this complex can act as a semiconductor with moderate conductivity.

Keywords: silver(I) polymeric structure; low conductivity semiconductor; one-dimensional coordination polymer; argentophilic interaction; electrical properties; crystal structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229618000128/yp3149sup1.cif Contains datablocks Global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229618000128/yp3149Isup2.hkl Contains datablock I
	Portable Document Format (PDF) file https://doi.org/10.1107/S2053229618000128/yp3149sup3.pdf IR and Raman spectra, and a brief theoretical background for the AIM analysis

CCDC reference: 1814355

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).

catena-Poly[[[aquatetrakis(µ₃-1,1-dioxo-1,2-benzisothiazole-3-thiolato-κ³N:S³:S³)tetrasilver(I)]-µ₂-4,4'-(propane-1,3-dyl)dipyridine-κ²N:N'] dimethyl sulfoxide hemisolvate] top

Crystal data top

[Ag₄(C₇H₄NO₂S₂)₄(C₁₃H₁₄N₂)(H₂O)]·0.5C₂H₆OS	Z = 2
M_r = 1479.75	F(000) = 1458
Triclinic, P1	D_x = 1.854 Mg m⁻³
a = 13.7710 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.9822 (4) Å	Cell parameters from 6300 reflections
c = 14.7181 (5) Å	θ = 3.6–26.1°
α = 81.074 (3)°	µ = 1.85 mm⁻¹
β = 79.523 (3)°	T = 290 K
γ = 73.152 (3)°	Fragment, yellow
V = 2651.23 (15) Å³	0.42 × 0.30 × 0.10 mm

Data collection top

Rigaku OD Xcalibur Eos Gemini diffractometer	11551 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	7060 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
Detector resolution: 16.0604 pixels mm^-1	θ_max = 29.0°, θ_min = 3.0°
ω scans	h = −17→14
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	k = −19→18
T_min = 0.50, T_max = 0.85	l = −19→19
26030 measured reflections

Refinement top

Refinement on F²	62 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.056	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.158	w = 1/[σ²(F_o²) + (0.0606P)² + 6.6052P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
11551 reflections	Δρ_max = 1.17 e Å⁻³
659 parameters	Δρ_min = −0.85 e Å⁻³

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Ag1	0.65543 (5)	0.22505 (5)	0.46035 (4)	0.07203 (19)
Ag2	0.88094 (4)	0.27268 (4)	0.23224 (4)	0.06322 (17)
Ag3	0.76014 (5)	0.09579 (5)	0.32270 (4)	0.06839 (18)
Ag4	0.66209 (5)	0.30577 (4)	0.23040 (5)	0.07152 (19)
S11	0.84966 (13)	0.21588 (13)	0.59344 (11)	0.0551 (4)
S21	0.92920 (14)	0.10318 (14)	0.33902 (11)	0.0610 (5)
O11	0.8151 (4)	0.1529 (4)	0.6700 (3)	0.0688 (13)
O21	0.8090 (4)	0.3215 (4)	0.5947 (4)	0.0749 (14)
N11	0.8288 (4)	0.1844 (4)	0.4955 (3)	0.0562 (14)
C11	0.9170 (5)	0.1469 (5)	0.4442 (4)	0.0538 (16)
C21	1.0095 (5)	0.1425 (5)	0.4830 (4)	0.0512 (15)
C31	1.1124 (6)	0.1069 (6)	0.4467 (5)	0.069 (2)
H31	1.131614	0.079417	0.390412	0.083*
C41	1.1838 (6)	0.1136 (7)	0.4961 (6)	0.084 (3)
H41	1.252856	0.091592	0.472183	0.100*
C51	1.1575 (7)	0.1517 (7)	0.5798 (6)	0.086 (3)
H51	1.208629	0.154018	0.612192	0.104*
C61	1.0564 (6)	0.1865 (6)	0.6168 (5)	0.0663 (19)
H61	1.038097	0.213381	0.673411	0.080*
C71	0.9836 (5)	0.1804 (5)	0.5678 (4)	0.0508 (15)
S12	0.90767 (14)	0.45315 (14)	0.35417 (13)	0.0613 (5)
S22	0.62518 (13)	0.40188 (13)	0.36506 (14)	0.0599 (4)
O12	0.9364 (4)	0.5197 (5)	0.2777 (4)	0.0888 (17)
O22	0.9875 (4)	0.3742 (4)	0.3914 (4)	0.0771 (15)
N12	0.8226 (4)	0.4027 (4)	0.3260 (4)	0.0542 (13)
C12	0.7336 (5)	0.4323 (5)	0.3765 (4)	0.0547 (16)
C22	0.7294 (5)	0.5008 (5)	0.4466 (5)	0.0561 (16)
C32	0.6476 (6)	0.5427 (6)	0.5116 (6)	0.073 (2)
H32	0.583357	0.532327	0.514579	0.087*
C42	0.6658 (8)	0.6011 (7)	0.5723 (7)	0.099 (3)
H42	0.613532	0.627817	0.618554	0.118*
C52	0.7595 (9)	0.6196 (7)	0.5647 (8)	0.101 (3)
H52	0.768754	0.660994	0.604262	0.121*
C62	0.8403 (7)	0.5784 (6)	0.5000 (6)	0.081 (2)
H62	0.904173	0.590096	0.495595	0.097*
C72	0.8223 (6)	0.5191 (5)	0.4420 (5)	0.0603 (17)
S13	0.77183 (17)	−0.04495 (15)	0.14420 (12)	0.0661 (5)
S23	0.79677 (17)	0.24580 (16)	0.09670 (13)	0.0706 (5)
O13	0.6707 (5)	−0.0539 (5)	0.1495 (4)	0.0920 (18)
O23	0.8391 (6)	−0.1206 (5)	0.1963 (4)	0.099 (2)
N13	0.7665 (5)	0.0683 (4)	0.1702 (4)	0.0658 (16)
C13	0.8007 (6)	0.1233 (6)	0.0992 (4)	0.0605 (18)
C23	0.8414 (5)	0.0700 (6)	0.0148 (4)	0.0565 (17)
C33	0.8920 (6)	0.1030 (6)	−0.0706 (5)	0.072 (2)
H33	0.903369	0.166448	−0.082209	0.086*
C43	0.9246 (6)	0.0342 (7)	−0.1378 (5)	0.078 (2)
H43	0.958826	0.053267	−0.195180	0.094*
C53	0.9087 (6)	−0.0566 (7)	−0.1227 (6)	0.080 (2)
H53	0.929421	−0.097954	−0.170315	0.096*
C63	0.8618 (6)	−0.0909 (6)	−0.0375 (5)	0.0645 (18)
H63	0.852797	−0.155356	−0.026103	0.077*
C73	0.8295 (5)	−0.0260 (5)	0.0287 (4)	0.0566 (16)
S14	0.4768 (3)	0.2283 (3)	0.1562 (4)	0.1564 (19)
S24	0.58604 (17)	0.09204 (16)	0.40010 (14)	0.0744 (6)
O14	0.5430 (12)	0.2127 (11)	0.0714 (8)	0.224 (8)
O24	0.4002 (9)	0.3222 (7)	0.1609 (11)	0.239 (8)
N14	0.5432 (5)	0.2110 (5)	0.2431 (6)	0.093 (2)
C14	0.5281 (5)	0.1352 (5)	0.3060 (6)	0.070 (2)
C24	0.4566 (6)	0.0842 (6)	0.2798 (8)	0.084 (3)
C34	0.4227 (6)	0.0062 (7)	0.3280 (8)	0.098 (3)
H34	0.443561	−0.021910	0.385174	0.117*
C44	0.3593 (8)	−0.0302 (9)	0.2928 (12)	0.139 (5)
H44	0.334741	−0.082728	0.326089	0.167*
C54	0.3305 (11)	0.0102 (10)	0.2072 (14)	0.191 (9)
H54	0.290155	−0.018167	0.181236	0.230*
C64	0.3598 (11)	0.0901 (10)	0.1607 (14)	0.194 (9)
H64	0.338601	0.119274	0.103853	0.233*
C74	0.4222 (8)	0.1268 (8)	0.2002 (10)	0.116 (4)
N15	0.5352 (5)	0.2612 (5)	0.5904 (5)	0.0738 (18)
N25	0.0154 (5)	0.3171 (4)	1.1297 (4)	0.0636 (15)
C15	0.5497 (6)	0.3145 (6)	0.6487 (6)	0.081 (2)
H15	0.606869	0.339695	0.635095	0.097*
C25	0.4839 (7)	0.3354 (7)	0.7301 (7)	0.102 (3)
H25	0.497345	0.375572	0.768450	0.122*
C35	0.4003 (9)	0.2993 (8)	0.7563 (7)	0.117 (2)
C45	0.3833 (7)	0.2470 (7)	0.6937 (7)	0.099 (3)
H45	0.325658	0.222573	0.705694	0.118*
C55	0.4503 (6)	0.2293 (6)	0.6120 (6)	0.081 (2)
H55	0.435691	0.193616	0.570298	0.097*
C65	0.0985 (6)	0.3269 (7)	1.1586 (6)	0.084 (2)
H65	0.107427	0.305888	1.220409	0.101*
C75	0.1716 (6)	0.3668 (7)	1.1009 (8)	0.101 (3)
H75	0.227885	0.371349	1.124832	0.121*
C85	0.1632 (8)	0.3997 (7)	1.0092 (8)	0.108 (2)
C95	0.0806 (6)	0.3843 (6)	0.9810 (6)	0.077 (2)
H95	0.072422	0.400772	0.918608	0.092*
C105	0.0090 (6)	0.3457 (5)	1.0403 (5)	0.0659 (19)
H105	−0.046711	0.339131	1.016770	0.079*
C115	0.3344 (8)	0.3133 (6)	0.8456 (7)	0.119 (2)
H11A	0.281135	0.279603	0.849357	0.143*
H11B	0.375009	0.280774	0.894774	0.143*
C125	0.2860 (8)	0.4175 (6)	0.8625 (7)	0.117 (2)
H12A	0.234327	0.443215	0.821442	0.140*
H12B	0.337977	0.453345	0.840643	0.140*
C135	0.2371 (8)	0.4496 (7)	0.9533 (6)	0.113 (2)
H13A	0.202733	0.520722	0.944030	0.135*
H13B	0.291114	0.442577	0.989975	0.135*
S1A	0.6847 (8)	0.4079 (6)	0.8253 (6)	0.133 (3)	0.328 (5)
O1A	0.6320 (12)	0.4694 (10)	0.9058 (11)	0.186 (9)	0.328 (5)
C1A	0.8110 (12)	0.4169 (19)	0.7950 (17)	0.22 (2)	0.328 (5)
H1A	0.844439	0.378155	0.744136	0.330*	0.328 (5)
H1B	0.810526	0.485971	0.776836	0.330*	0.328 (5)
H1C	0.847147	0.391445	0.847388	0.330*	0.328 (5)
C2A	0.6862 (17)	0.2819 (7)	0.8598 (14)	0.127 (8)	0.328 (5)
H2A	0.719371	0.242681	0.809211	0.191*	0.328 (5)
H2B	0.722893	0.257230	0.911939	0.191*	0.328 (5)
H2C	0.617077	0.276749	0.877144	0.191*	0.328 (5)
S1B	0.7251 (11)	0.3810 (9)	0.8874 (12)	0.133 (3)	0.172 (5)
O1B	0.6320 (12)	0.4694 (10)	0.9058 (11)	0.186 (9)	0.172 (5)
C1B	0.8110 (12)	0.4169 (19)	0.7950 (17)	0.22 (2)	0.172 (5)
H1D	0.869773	0.360862	0.783539	0.330*	0.172 (5)
H1E	0.778031	0.438247	0.740327	0.330*	0.172 (5)
H1F	0.832267	0.471290	0.810252	0.330*	0.172 (5)
C2B	0.6862 (17)	0.2819 (7)	0.8598 (14)	0.127 (8)	0.172 (5)
H2D	0.744977	0.225914	0.848166	0.191*	0.172 (5)
H2E	0.639151	0.262109	0.910763	0.191*	0.172 (5)
H2F	0.653021	0.303303	0.805264	0.191*	0.172 (5)
O1W	0.5624 (10)	0.4406 (7)	0.1121 (8)	0.184 (5)
H1WA	0.523 (13)	0.505 (4)	0.088 (12)	0.275*
H1WB	0.550 (3)	0.395 (8)	0.077 (8)	0.275*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.0633 (4)	0.0866 (4)	0.0619 (4)	−0.0244 (3)	0.0095 (3)	−0.0088 (3)
Ag2	0.0624 (3)	0.0821 (4)	0.0466 (3)	−0.0265 (3)	0.0027 (2)	−0.0102 (3)
Ag3	0.0698 (4)	0.0936 (4)	0.0426 (3)	−0.0252 (3)	−0.0023 (3)	−0.0107 (3)
Ag4	0.0654 (4)	0.0731 (4)	0.0835 (4)	−0.0293 (3)	−0.0065 (3)	−0.0152 (3)
S11	0.0542 (10)	0.0723 (11)	0.0373 (8)	−0.0190 (8)	−0.0006 (7)	−0.0047 (7)
S21	0.0628 (11)	0.0771 (11)	0.0354 (8)	−0.0121 (9)	0.0025 (7)	−0.0081 (8)
O11	0.070 (3)	0.098 (4)	0.042 (3)	−0.038 (3)	−0.003 (2)	0.003 (2)
O21	0.072 (3)	0.074 (3)	0.071 (3)	−0.004 (3)	−0.004 (3)	−0.021 (3)
N11	0.051 (3)	0.074 (4)	0.037 (3)	−0.007 (3)	−0.007 (2)	−0.005 (2)
C11	0.049 (4)	0.069 (4)	0.039 (3)	−0.016 (3)	−0.006 (3)	0.006 (3)
C21	0.054 (4)	0.052 (3)	0.042 (3)	−0.015 (3)	−0.002 (3)	0.006 (3)
C31	0.052 (4)	0.095 (5)	0.052 (4)	−0.013 (4)	0.001 (3)	−0.004 (4)
C41	0.053 (5)	0.128 (7)	0.063 (5)	−0.024 (5)	−0.009 (4)	0.009 (5)
C51	0.061 (5)	0.123 (7)	0.079 (6)	−0.035 (5)	−0.024 (5)	0.012 (5)
C61	0.073 (5)	0.077 (5)	0.052 (4)	−0.028 (4)	−0.018 (4)	0.009 (3)
C71	0.050 (4)	0.060 (4)	0.043 (3)	−0.020 (3)	−0.009 (3)	0.007 (3)
S12	0.0549 (10)	0.0743 (11)	0.0622 (11)	−0.0306 (9)	−0.0107 (8)	−0.0019 (9)
S22	0.0451 (9)	0.0628 (10)	0.0737 (12)	−0.0176 (8)	−0.0049 (8)	−0.0112 (9)
O12	0.079 (4)	0.109 (4)	0.090 (4)	−0.059 (3)	−0.010 (3)	0.012 (3)
O22	0.057 (3)	0.088 (4)	0.087 (4)	−0.015 (3)	−0.016 (3)	−0.013 (3)
N12	0.047 (3)	0.060 (3)	0.058 (3)	−0.020 (3)	−0.001 (3)	−0.012 (3)
C12	0.062 (4)	0.060 (4)	0.047 (4)	−0.027 (3)	−0.009 (3)	0.002 (3)
C22	0.055 (4)	0.052 (4)	0.060 (4)	−0.010 (3)	−0.014 (3)	−0.004 (3)
C32	0.054 (4)	0.079 (5)	0.083 (5)	−0.004 (4)	−0.014 (4)	−0.024 (4)
C42	0.095 (7)	0.094 (6)	0.104 (7)	−0.003 (6)	−0.017 (6)	−0.042 (6)
C52	0.105 (8)	0.083 (6)	0.127 (9)	−0.011 (6)	−0.034 (7)	−0.053 (6)
C62	0.091 (6)	0.074 (5)	0.092 (6)	−0.028 (5)	−0.031 (5)	−0.015 (5)
C72	0.064 (5)	0.058 (4)	0.063 (4)	−0.018 (3)	−0.022 (4)	−0.003 (3)
S13	0.0841 (14)	0.0762 (12)	0.0419 (9)	−0.0343 (11)	−0.0004 (9)	−0.0039 (8)
S23	0.0935 (15)	0.0871 (13)	0.0480 (10)	−0.0530 (12)	−0.0116 (10)	−0.0007 (9)
O13	0.088 (4)	0.102 (4)	0.093 (4)	−0.051 (3)	0.019 (3)	−0.018 (3)
O23	0.138 (6)	0.094 (4)	0.060 (3)	−0.027 (4)	−0.029 (4)	0.015 (3)
N13	0.090 (5)	0.080 (4)	0.035 (3)	−0.042 (3)	0.003 (3)	−0.007 (3)
C13	0.072 (5)	0.091 (5)	0.034 (3)	−0.045 (4)	−0.009 (3)	−0.006 (3)
C23	0.050 (4)	0.094 (5)	0.031 (3)	−0.027 (4)	−0.009 (3)	−0.002 (3)
C33	0.070 (5)	0.099 (6)	0.049 (4)	−0.040 (4)	−0.001 (4)	0.006 (4)
C43	0.076 (5)	0.120 (7)	0.032 (4)	−0.027 (5)	0.007 (3)	−0.005 (4)
C53	0.076 (6)	0.104 (7)	0.055 (5)	−0.019 (5)	0.000 (4)	−0.015 (4)
C63	0.066 (5)	0.075 (5)	0.049 (4)	−0.009 (4)	−0.009 (3)	−0.013 (3)
C73	0.056 (4)	0.072 (4)	0.042 (4)	−0.019 (3)	−0.010 (3)	0.000 (3)
S14	0.156 (3)	0.136 (3)	0.223 (4)	−0.100 (3)	−0.140 (3)	0.094 (3)
S24	0.0768 (13)	0.0880 (13)	0.0605 (11)	−0.0384 (11)	0.0086 (10)	−0.0054 (10)
O14	0.323 (17)	0.298 (15)	0.148 (9)	−0.224 (14)	−0.170 (11)	0.113 (10)
O24	0.176 (10)	0.115 (6)	0.46 (2)	−0.062 (7)	−0.210 (13)	0.117 (9)
N14	0.080 (5)	0.084 (4)	0.128 (6)	−0.045 (4)	−0.052 (5)	0.035 (4)
C14	0.049 (4)	0.053 (4)	0.103 (6)	−0.015 (3)	0.004 (4)	−0.011 (4)
C24	0.049 (4)	0.063 (5)	0.139 (8)	−0.020 (4)	−0.011 (5)	−0.004 (5)
C34	0.054 (5)	0.082 (6)	0.162 (10)	−0.037 (4)	−0.003 (5)	−0.003 (6)
C44	0.082 (7)	0.101 (8)	0.245 (17)	−0.049 (6)	−0.049 (9)	0.024 (9)
C54	0.162 (13)	0.130 (10)	0.34 (2)	−0.101 (10)	−0.171 (16)	0.085 (13)
C64	0.173 (13)	0.129 (10)	0.34 (2)	−0.090 (10)	−0.191 (15)	0.083 (12)
C74	0.087 (7)	0.102 (7)	0.180 (11)	−0.051 (6)	−0.069 (8)	0.033 (7)
N15	0.054 (4)	0.089 (4)	0.072 (4)	−0.022 (3)	0.015 (3)	−0.012 (4)
N25	0.058 (4)	0.079 (4)	0.053 (3)	−0.024 (3)	0.006 (3)	−0.010 (3)
C15	0.059 (5)	0.083 (5)	0.093 (6)	−0.017 (4)	0.014 (4)	−0.020 (5)
C25	0.095 (7)	0.094 (6)	0.112 (8)	−0.035 (5)	0.040 (6)	−0.048 (6)
C35	0.114 (4)	0.100 (4)	0.124 (4)	−0.051 (3)	0.066 (4)	−0.033 (3)
C45	0.076 (6)	0.093 (6)	0.113 (8)	−0.033 (5)	0.036 (5)	−0.009 (6)
C55	0.069 (5)	0.093 (6)	0.072 (5)	−0.019 (5)	0.005 (4)	−0.006 (4)
C65	0.063 (5)	0.125 (7)	0.068 (5)	−0.030 (5)	−0.006 (4)	−0.018 (5)
C75	0.037 (4)	0.118 (7)	0.148 (10)	−0.031 (5)	0.022 (5)	−0.037 (7)
C85	0.103 (4)	0.096 (4)	0.120 (4)	−0.053 (3)	0.062 (4)	−0.039 (3)
C95	0.074 (5)	0.077 (5)	0.067 (5)	−0.023 (4)	0.025 (4)	−0.007 (4)
C105	0.057 (4)	0.071 (4)	0.068 (5)	−0.020 (4)	0.005 (4)	−0.011 (4)
C115	0.116 (4)	0.103 (3)	0.126 (4)	−0.051 (3)	0.066 (3)	−0.032 (3)
C125	0.113 (4)	0.102 (3)	0.125 (4)	−0.052 (3)	0.064 (3)	−0.033 (3)
C135	0.107 (4)	0.100 (3)	0.123 (4)	−0.053 (3)	0.062 (3)	−0.036 (3)
S1A	0.193 (10)	0.098 (5)	0.105 (7)	−0.011 (6)	−0.056 (6)	−0.015 (5)
O1A	0.19 (2)	0.145 (15)	0.19 (2)	0.001 (14)	0.008 (16)	−0.073 (14)
C1A	0.20 (3)	0.22 (3)	0.30 (4)	−0.13 (3)	0.07 (3)	−0.21 (3)
C2A	0.14 (2)	0.123 (17)	0.103 (16)	0.016 (15)	−0.065 (15)	−0.003 (13)
S1B	0.193 (10)	0.098 (5)	0.105 (7)	−0.011 (6)	−0.056 (6)	−0.015 (5)
O1B	0.19 (2)	0.145 (15)	0.19 (2)	0.001 (14)	0.008 (16)	−0.073 (14)
C1B	0.20 (3)	0.22 (3)	0.30 (4)	−0.13 (3)	0.07 (3)	−0.21 (3)
C2B	0.14 (2)	0.123 (17)	0.103 (16)	0.016 (15)	−0.065 (15)	−0.003 (13)
O1W	0.231 (12)	0.141 (7)	0.220 (11)	−0.094 (8)	−0.116 (9)	0.041 (7)

Geometric parameters (Å, º) top

Ag1—N15	2.307 (6)	C63—H63	0.9300
Ag1—N11	2.422 (5)	S14—O14	1.411 (15)
Ag1—S22	2.607 (2)	S14—O24	1.429 (12)
Ag1—S24	2.647 (2)	S14—N14	1.653 (8)
Ag1—Ag3	2.8307 (8)	S14—C74	1.776 (10)
Ag2—N12	2.320 (5)	S24—C14	1.668 (9)
Ag2—N25ⁱ	2.335 (6)	N14—C14	1.333 (10)
Ag2—S23	2.606 (2)	C14—C24	1.502 (11)
Ag2—S21	2.615 (2)	C24—C74	1.331 (14)
Ag2—Ag4	2.9180 (8)	C24—C34	1.359 (11)
Ag2—Ag3	3.3489 (8)	C34—C44	1.340 (14)
Ag3—N13	2.317 (5)	C34—H34	0.9300
Ag3—S21	2.416 (2)	C44—C54	1.376 (19)
Ag3—S24	2.472 (2)	C44—H44	0.9300
Ag3—Ag4	3.0692 (9)	C54—C64	1.343 (17)
Ag4—N14	2.354 (6)	C54—H54	0.9300
Ag4—S22	2.461 (2)	C64—C74	1.367 (15)
Ag4—S23	2.510 (2)	C64—H64	0.9300
Ag4—O1W	2.612 (9)	N15—C15	1.296 (10)
S11—O11	1.418 (5)	N15—C55	1.337 (10)
S11—O21	1.421 (5)	N25—C105	1.325 (9)
S11—N11	1.665 (6)	N25—C65	1.340 (10)
S11—C71	1.751 (7)	C15—C25	1.379 (11)
S21—C11	1.714 (7)	C15—H15	0.9300
N11—C11	1.319 (8)	C25—C35	1.358 (13)
C11—C21	1.470 (9)	C25—H25	0.9300
C21—C71	1.379 (9)	C35—C45	1.351 (14)
C21—C31	1.393 (9)	C35—C115	1.460 (6)
C31—C41	1.355 (11)	C45—C55	1.384 (11)
C31—H31	0.9300	C45—H45	0.9300
C41—C51	1.364 (12)	C55—H55	0.9300
C41—H41	0.9300	C65—C75	1.384 (12)
C51—C61	1.373 (11)	C65—H65	0.9300
C51—H51	0.9300	C75—C85	1.370 (15)
C61—C71	1.365 (9)	C75—H75	0.9300
C61—H61	0.9300	C85—C95	1.362 (14)
S12—O12	1.420 (6)	C85—C135	1.460 (6)
S12—O22	1.434 (5)	C95—C105	1.369 (10)
S12—N12	1.670 (6)	C95—H95	0.9300
S12—C72	1.759 (8)	C105—H105	0.9300
S22—C12	1.709 (7)	C115—C125	1.455 (6)
N12—C12	1.302 (8)	C115—H11A	0.9700
C12—C22	1.496 (9)	C115—H11B	0.9700
C22—C72	1.363 (10)	C125—C135	1.457 (6)
C22—C32	1.387 (10)	C125—H12A	0.9700
C32—C42	1.399 (12)	C125—H12B	0.9700
C32—H32	0.9300	C135—H13A	0.9700
C42—C52	1.370 (13)	C135—H13B	0.9700
C42—H42	0.9300	S1A—O1A	1.520 (3)
C52—C62	1.374 (13)	S1A—C1A	1.751 (3)
C52—H52	0.9300	S1A—C2A	1.752 (3)
C62—C72	1.376 (10)	C1A—H1A	0.9600
C62—H62	0.9300	C1A—H1B	0.9600
S13—O23	1.415 (6)	C1A—H1C	0.9600
S13—O13	1.421 (6)	C2A—H2A	0.9600
S13—N13	1.664 (6)	C2A—H2B	0.9600
S13—C73	1.756 (7)	C2A—H2C	0.9600
S23—C13	1.693 (8)	S1B—O1B	1.517 (3)
N13—C13	1.300 (8)	S1B—C1B	1.746 (3)
C13—C23	1.485 (9)	S1B—C2B	1.749 (3)
C23—C73	1.379 (10)	C1B—H1D	0.9600
C23—C33	1.403 (9)	C1B—H1E	0.9600
C33—C43	1.409 (11)	C1B—H1F	0.9600
C33—H33	0.9300	C2B—H2D	0.9600
C43—C53	1.330 (11)	C2B—H2E	0.9600
C43—H43	0.9300	C2B—H2F	0.9600
C53—C63	1.384 (10)	O1W—H1WA	0.956 (10)
C53—H53	0.9300	O1W—H1WB	0.953 (10)
C63—C73	1.362 (9)

N15—Ag1—N11	111.9 (2)	C73—C23—C13	112.0 (6)
N15—Ag1—S22	100.45 (17)	C33—C23—C13	128.7 (7)
N11—Ag1—S22	105.35 (14)	C23—C33—C43	116.0 (7)
N15—Ag1—S24	99.32 (19)	C23—C33—H33	122.0
N11—Ag1—S24	121.61 (14)	C43—C33—H33	122.0
S22—Ag1—S24	116.15 (7)	C53—C43—C33	122.9 (7)
N15—Ag1—Ag3	150.49 (18)	C53—C43—H43	118.6
N11—Ag1—Ag3	79.72 (13)	C33—C43—H43	118.6
S22—Ag1—Ag3	102.32 (5)	C43—C53—C63	121.4 (8)
S24—Ag1—Ag3	53.52 (5)	C43—C53—H53	119.3
N12—Ag2—N25ⁱ	102.99 (19)	C63—C53—H53	119.3
N12—Ag2—S23	127.40 (15)	C73—C63—C53	116.9 (8)
N25ⁱ—Ag2—S23	92.24 (16)	C73—C63—H63	121.6
N12—Ag2—S21	108.22 (14)	C53—C63—H63	121.6
N25ⁱ—Ag2—S21	116.38 (16)	C63—C73—C23	123.5 (6)
S23—Ag2—S21	109.02 (6)	C63—C73—S13	129.4 (6)
N12—Ag2—Ag4	82.64 (13)	C23—C73—S13	107.1 (5)
N25ⁱ—Ag2—Ag4	135.26 (16)	O14—S14—O24	117.3 (8)
S23—Ag2—Ag4	53.68 (5)	O14—S14—N14	110.7 (6)
S21—Ag2—Ag4	103.06 (5)	O24—S14—N14	108.5 (7)
N12—Ag2—Ag3	107.90 (13)	O14—S14—C74	113.0 (8)
N25ⁱ—Ag2—Ag3	148.13 (15)	O24—S14—C74	110.7 (7)
S23—Ag2—Ag3	75.23 (4)	N14—S14—C74	94.2 (5)
S21—Ag2—Ag3	45.78 (5)	C14—S24—Ag3	96.3 (3)
Ag4—Ag2—Ag3	58.163 (19)	C14—S24—Ag1	114.3 (3)
N13—Ag3—S21	106.92 (16)	Ag3—S24—Ag1	67.04 (6)
N13—Ag3—S24	105.52 (17)	C14—N14—S14	112.5 (6)
S21—Ag3—S24	147.31 (7)	C14—N14—Ag4	129.5 (6)
N13—Ag3—Ag1	143.77 (16)	S14—N14—Ag4	117.5 (4)
S21—Ag3—Ag1	95.14 (5)	N14—C14—C24	112.3 (8)
S24—Ag3—Ag1	59.44 (5)	N14—C14—S24	126.2 (6)
N13—Ag3—Ag4	76.88 (15)	C24—C14—S24	121.4 (6)
S21—Ag3—Ag4	103.82 (5)	C74—C24—C34	119.4 (9)
S24—Ag3—Ag4	87.29 (6)	C74—C24—C14	112.3 (8)
Ag1—Ag3—Ag4	70.03 (2)	C34—C24—C14	128.2 (10)
N13—Ag3—Ag2	85.74 (14)	C44—C34—C24	119.7 (12)
S21—Ag3—Ag2	50.87 (5)	C44—C34—H34	120.1
S24—Ag3—Ag2	136.51 (6)	C24—C34—H34	120.1
Ag1—Ag3—Ag2	86.51 (2)	C34—C44—C54	119.8 (11)
Ag4—Ag3—Ag2	53.872 (18)	C34—C44—H44	120.1
N14—Ag4—S22	110.2 (2)	C54—C44—H44	120.1
N14—Ag4—S23	105.5 (2)	C64—C54—C44	121.0 (12)
S22—Ag4—S23	143.14 (7)	C64—C54—H54	119.5
N14—Ag4—O1W	90.5 (3)	C44—C54—H54	119.5
S22—Ag4—O1W	100.3 (3)	C54—C64—C74	117.2 (13)
S23—Ag4—O1W	88.2 (3)	C54—C64—H64	121.4
N14—Ag4—Ag2	138.93 (18)	C74—C64—H64	121.4
S22—Ag4—Ag2	89.29 (5)	C24—C74—C64	122.5 (10)
S23—Ag4—Ag2	56.79 (5)	C24—C74—S14	108.7 (7)
O1W—Ag4—Ag2	122.1 (3)	C64—C74—S14	128.6 (10)
N14—Ag4—Ag3	73.22 (16)	C15—N15—C55	116.2 (7)
S22—Ag4—Ag3	99.45 (5)	C15—N15—Ag1	119.2 (5)
S23—Ag4—Ag3	81.93 (5)	C55—N15—Ag1	124.6 (6)
O1W—Ag4—Ag3	157.8 (2)	C105—N25—C65	115.3 (7)
Ag2—Ag4—Ag3	67.97 (2)	C105—N25—Ag2ⁱⁱ	121.8 (5)
O11—S11—O21	117.6 (3)	C65—N25—Ag2ⁱⁱ	122.4 (5)
O11—S11—N11	109.3 (3)	N15—C15—C25	122.7 (8)
O21—S11—N11	108.5 (3)	N15—C15—H15	118.7
O11—S11—C71	111.1 (3)	C25—C15—H15	118.7
O21—S11—C71	112.3 (3)	C35—C25—C15	122.4 (9)
N11—S11—C71	95.7 (3)	C35—C25—H25	118.8
C11—S21—Ag3	106.1 (2)	C15—C25—H25	118.8
C11—S21—Ag2	100.6 (2)	C45—C35—C25	114.7 (8)
Ag3—S21—Ag2	83.35 (6)	C45—C35—C115	121.9 (10)
C11—N11—S11	110.0 (5)	C25—C35—C115	123.4 (10)
C11—N11—Ag1	130.0 (4)	C35—C45—C55	121.0 (9)
S11—N11—Ag1	119.7 (3)	C35—C45—H45	119.5
N11—C11—C21	115.8 (6)	C55—C45—H45	119.5
N11—C11—S21	124.7 (5)	N15—C55—C45	123.0 (9)
C21—C11—S21	119.5 (5)	N15—C55—H55	118.5
C71—C21—C31	119.6 (7)	C45—C55—H55	118.5
C71—C21—C11	110.7 (6)	N25—C65—C75	123.0 (9)
C31—C21—C11	129.7 (6)	N25—C65—H65	118.5
C41—C31—C21	117.9 (7)	C75—C65—H65	118.5
C41—C31—H31	121.0	C85—C75—C65	121.7 (9)
C21—C31—H31	121.0	C85—C75—H75	119.2
C31—C41—C51	122.0 (8)	C65—C75—H75	119.2
C31—C41—H41	119.0	C75—C85—C95	113.8 (7)
C51—C41—H41	119.0	C75—C85—C135	119.6 (12)
C41—C51—C61	120.8 (8)	C95—C85—C135	126.6 (12)
C41—C51—H51	119.6	C105—C95—C85	122.9 (9)
C61—C51—H51	119.6	C105—C95—H95	118.6
C71—C61—C51	117.9 (8)	C85—C95—H95	118.6
C71—C61—H61	121.1	N25—C105—C95	123.1 (8)
C51—C61—H61	121.1	N25—C105—H105	118.4
C61—C71—C21	121.7 (6)	C95—C105—H105	118.4
C61—C71—S11	130.4 (6)	C125—C115—C35	115.0 (8)
C21—C71—S11	107.9 (5)	C125—C115—H11A	108.5
O12—S12—O22	117.9 (4)	C35—C115—H11A	108.5
O12—S12—N12	109.1 (3)	C125—C115—H11B	108.5
O22—S12—N12	108.9 (3)	C35—C115—H11B	108.5
O12—S12—C72	111.5 (4)	H11A—C115—H11B	107.5
O22—S12—C72	111.7 (3)	C115—C125—C135	124.1 (9)
N12—S12—C72	95.3 (3)	C115—C125—H12A	106.3
C12—S22—Ag4	108.8 (2)	C135—C125—H12A	106.3
C12—S22—Ag1	100.2 (2)	C115—C125—H12B	106.3
Ag4—S22—Ag1	83.95 (6)	C135—C125—H12B	106.3
C12—N12—S12	110.8 (5)	H12A—C125—H12B	106.4
C12—N12—Ag2	129.0 (4)	C125—C135—C85	119.3 (8)
S12—N12—Ag2	118.8 (3)	C125—C135—H13A	107.5
N12—C12—C22	115.1 (6)	C85—C135—H13A	107.5
N12—C12—S22	125.0 (5)	C125—C135—H13B	107.5
C22—C12—S22	119.9 (5)	C85—C135—H13B	107.5
C72—C22—C32	120.3 (7)	H13A—C135—H13B	107.0
C72—C22—C12	110.8 (6)	O1A—S1A—C1A	109.3 (6)
C32—C22—C12	128.9 (7)	O1A—S1A—C2A	109.1 (6)
C22—C32—C42	117.3 (8)	C1A—S1A—C2A	109.2 (12)
C22—C32—H32	121.3	S1A—C1A—H1A	109.5
C42—C32—H32	121.3	S1A—C1A—H1B	109.5
C52—C42—C32	120.9 (9)	H1A—C1A—H1B	109.5
C52—C42—H42	119.6	S1A—C1A—H1C	109.5
C32—C42—H42	119.6	H1A—C1A—H1C	109.5
C42—C52—C62	121.6 (8)	H1B—C1A—H1C	109.5
C42—C52—H52	119.2	S1A—C2A—H2A	109.5
C62—C52—H52	119.2	S1A—C2A—H2B	109.5
C72—C62—C52	117.0 (8)	H2A—C2A—H2B	109.5
C72—C62—H62	121.5	S1A—C2A—H2C	109.5
C52—C62—H62	121.5	H2A—C2A—H2C	109.5
C22—C72—C62	122.9 (7)	H2B—C2A—H2C	109.5
C22—C72—S12	108.1 (5)	O1B—S1B—C1B	109.6 (6)
C62—C72—S12	129.1 (6)	O1B—S1B—C2B	109.3 (7)
O23—S13—O13	117.0 (4)	C1B—S1B—C2B	109.6 (12)
O23—S13—N13	110.4 (4)	S1B—C1B—H1D	109.5
O13—S13—N13	109.4 (4)	S1B—C1B—H1E	109.5
O23—S13—C73	110.9 (4)	H1D—C1B—H1E	109.5
O13—S13—C73	111.9 (4)	S1B—C1B—H1F	109.5
N13—S13—C73	95.0 (3)	H1D—C1B—H1F	109.5
C13—S23—Ag4	104.2 (2)	H1E—C1B—H1F	109.5
C13—S23—Ag2	110.9 (2)	S1B—C2B—H2D	109.5
Ag4—S23—Ag2	69.53 (5)	S1B—C2B—H2E	109.5
C13—N13—S13	112.2 (5)	H2D—C2B—H2E	109.5
C13—N13—Ag3	123.1 (5)	S1B—C2B—H2F	109.5
S13—N13—Ag3	120.6 (3)	H2D—C2B—H2F	109.5
N13—C13—C23	113.6 (6)	H2E—C2B—H2F	109.5
N13—C13—S23	125.5 (5)	Ag4—O1W—H1WA	158 (9)
C23—C13—S23	120.9 (5)	Ag4—O1W—H1WB	97 (9)
C73—C23—C33	119.2 (7)	H1WA—O1W—H1WB	103.4 (15)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WB···O14	0.95 (10)	2.59 (11)	3.425 (18)	147 (9)
O1W—H1WB···O24	0.95 (10)	2.59 (8)	3.072 (18)	112 (8)
O1W—H1WA···O1Aⁱⁱⁱ	0.96 (9)	2.05 (18)	2.65 (2)	119 (12)
C125—H12B···O1Wⁱⁱⁱ	0.97	2.53	3.369 (17)	144
C44—H44···O11^iv	0.93	2.52	3.260 (13)	137
C53—H53···S21^v	0.93	2.86	3.572 (9)	134
C75—H75···O24^vi	0.93	2.41	3.284 (16)	158
C105—H105···S23ⁱⁱ	0.93	2.82	3.508 (9)	132

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

Selected bond lengths in (I) (Å) top

Ag1—N15	2.307 (6)	Ag3—N13	2.317 (5)
Ag1—N11	2.422 (5)	Ag3—S21	2.416 (2)
Ag1—S22	2.607 (2)	Ag3—S24	2.472 (2)
Ag1—S24	2.647 (2)	Ag4—N14	2.354 (6)
Ag2—N12	2.320 (5)	Ag4—S22	2.461 (2)
Ag2—N25ⁱ	2.335 (6)	Ag4—S23	2.510 (2)
Ag2—S23	2.606 (2)	Ag4···O1W	2.612 (9)
Ag2—S21	2.615 (2)

Ag1···Ag3	2.8307 (8)	Ag3···Ag4	3.0692 (9)
Ag2···Ag4	2.9180 (8)	Ag2···Ag3	3.3489 (8)

Symmetry code: (i) x+1, y, z-1.

S═O···π bonds in (I) top

S═O···Cg	O···Cg (Å)	O/perp (Å)	O···Cg/perp (°)	S═O/perp (°)
S13═O13···Cg4	3.533 (8)	3.428	30.30	111.5 (3)
S14═O14···Cg3	3.718 (9)	3.440	13.41	115.5 (7)
S11═O21···Cg2	3.343 (6)	3.124	46.34	116.9 (3)
S12═O22···Cg1	3.388 (6)	3.244	41.68	116.6 (3)

O/perp is the perpendicular distances of O to the plane, O···Cg/perp is the angle between the O···Cg vector and the plane normal, and S═O/perpa is the angle between the S═O vector and the plane normal.

Cg1 is the centroid of the S11/N11/C11/C21/C71 ring, Cg2 that of the S12/N12/C12/C22/C72 ring, Cg3 that of the S13/N13/C13/C23/C73 and Cg4 that of the S14/N14/C14/C24/C74 ring.

Comparative table showing the relative strengths of argentophilic interactions in (I), as compared with selected covalent and noncovalent ones top

Interaction	#CP	Contact	Distance	ρ(r)(r) (× 100)	\nabla²ρ(r) (\rimes 10)
Ag···Ag	CP1	Ag1···Ag3	2.8307 (8)	3.23	0.80
	CP3	Ag3···Ag4	3.0692 (9)	1.99	0.51
	CP2	Ag4···Ag2	2.9180 (8)	2.75	0.69
	CP4	Ag4···O1W	2.612 (9)	2.66	0.85

O···π		O13···Cg4	3.533 (8)	0.37	0.14
		O14···Cg3	3.718 (9)	0.36	0.15
		O21···Cg2	3.343 (6)	0.68	0.25
		O22···Cg1	3.388 (6)	0.53	0.19

S—Ag		S21-Ag3	2.416 (2)	7.21	1.90
		S21—Ag2	2.615 (2)	4.77	1.23
		S22—Ag1	2.607 (2)	4.85	1.25
		S22—Ag4	2.461 (2)	6.59	1.74
		S23—Ag2	2.606 (2)	4.90	1.25
		S23—Ag4	2.510 (2)	6.03	1.50
		S24—Ag1	2.647 (2)	4.63	1.17
		S24—Ag3	2.472 (2)	6.43	1.59

Cg1 is the centroid of the S11/N11/C11/C21/C71 ring, Cg2 that of the S12/N12/C12/C22/C72 ring, Cg3 that of the S13/N13/C13/C23/C73. [Added, OK?]

Electric conductivity and argentophilic interactions in (I), (II) and (III) top

Compound	EC (S cm^-1)	Ag···Ag (Å)	Bridging mode
(I)	2.5 10^-8	2.830	N—Ag
(II)	2.9 10^-7	2.886	N—Ag
(III)	9.5 10^-3	3.024	S—Ag

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Structure and electrical properties of a one-dimensional polymeric silver thio­saccharinate complex with argentophilic inter­actions

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Structure and electrical properties of a one-dimensional polymeric silver thiosaccharinate complex with argentophilic interactions