Phyllo-poly[[μ2-1,4-bis­(cyclo­hexyl­sulfanylmeth­yl)benzene-κ2S:S′](μ2-nitrato-κ2O:O′)silver(I)]

Kim, T.H.; Shin, Y.W.; Park, K.-M.; Kim, J.

doi:10.1107/S1600536809007910

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page m385

doi:10.1107/S1600536809007910

Open

access

Phyllo-poly[[μ₂-1,4-bis(cyclohexylsulfanylmethyl)benzene-κ²S:S′](μ₂-nitrato-κ²O:O′)silver(I)]

Tae Ho Kim,^a Yong Woon Shin,^b Ki-Min Park ^c and Jineun Kim ^d ^*

^aDepartment of Chemistry, Gyeongsang National University, Jinju 660-701, Republic of Korea, ^bTest & Analytical Laboratory, Korea Food & Drug Administration, 123-7 Yongdang-dong, Busan 608-829, Republic of Korea, ^cResearch Institute of Natural Sciences, Gyeongsang National University, Jinju 660-701, Republic of Korea, and ^dDepartment of Chemistry, Gyeongsang National University, Jinju 660-701, Republic of Korea
^*Correspondence e-mail: jekim@gnu.ac.kr

(Received 15 February 2009; accepted 4 March 2009; online 11 March 2009)

The title compound, [Ag(NO₃)(C₂₀H₃₀S₂)]_n, was synthesized by the reaction of silver nitrate and 1,4-bis(cyclohexylthiomethyl)benzene (bctmb) in acetonitrile. The coordination polymer exhibits a two-dimensional layer structure. The layers are wave-like and parallel to the crystallographic ac plane; Ag^I ions are linked by the bctmb ligands and nitrate anions along the crystallographic a and c directions, respectively. In addition, the crystal structure is stabilized by C—H⋯O hydrogen bonds.

Related literature

For the synthesis of the ligand, see: Kim et al. (2008 ). For related structures, see: Kim et al. (2007 ). For structures with Ni(II) in trigonal-pyramidal coordination, see: Cho et al. (2007 ). For potential applications of coordination polymers, see: Young & Hanton (2008 ).

Experimental

Crystal data

[Ag(NO₃)(C₂₀H₃₀S₂)]
M_r = 504.44
Monoclinic, P 2₁ /c
a = 12.1053 (6) Å
b = 20.719 (1) Å
c = 8.5973 (4) Å
β = 92.256 (1)°
V = 2154.61 (18) Å³
Z = 4
Mo Kα radiation
μ = 1.15 mm⁻¹
T = 173 K
0.30 × 0.20 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.724, T_max = 0.894
13362 measured reflections
4804 independent reflections
3174 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.115
S = 1.04
4804 reflections
238 parameters
H-atom parameters constrained
Δρ_max = 0.90 e Å⁻³
Δρ_min = −1.00 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14A⋯O3ⁱ	0.99	2.60	3.416 (7)	140
C14—H14B⋯O3ⁱⁱ	0.99	2.47	3.199 (6)	130
C7—H7B⋯O2ⁱⁱⁱ	0.99	2.43	3.118 (6)	126
Symmetry codes: (i) $[x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) x-1, y, z; (iii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2000 ); cell refinement: SAINT-Plus (Bruker, 2000); data reduction: SAINT-Plus; 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809007910/lx2093sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809007910/lx2093Isup2.hkl

checkCIF report

Comment top

An increasing interest has been directed toward the study of new coordination polymers owing to potential applications (Young & Hanton, 2008). The scant research on the coordination polymers with dithioether ligands prompted us to investigate the possibility of diverse structures. Therefore, we designed and synthesized 1,4-bis(cyclohexylthiomethyl)benzene (bctmb) as a dithioether ligand. Synthesis of the bctmb ligand has been published previously (Kim, et al., 2008).

The title compound, phyllo-poly[(µ₂-nitrato-κ² O:O')(µ₂-1,4-bis(cyclohexylthiomethyl)benzene- κ² S:S') silver(I)], [Ag(NO₃)(C₂₀H₃₀S₂)]_n was synthesized by self-assembly of silver nitrate and the bctmb ligand in acetonitrile (Kim et al., 2007) (Fig. 1). The coordination number of Ag is four and the Ag atom is a slightly distorted trigonal pyramidal geometry, in which an O atom (O2) from nitrate anion and two S atoms from two different bctmb ligands form a basal plane and an O atom (O1) from neighboring nitrate anion is occupied apical position. The Ag atom is slightly apart from this basal plane (0.123 (2) Å). Each Ag^I ions is linked by the bctmb ligands to form 1D chain along the a axis. These chains are connected by bidentate nitrate anions in a bridging mode to generate 2D layer structure, as shown in Fig. 2. The layers are wavy and parallel to the crystallographic ac plane. The packing structure is stabilized by C—H···O hydrogen bonds (Table 1 & Fig. 2).

Related literature top

For the synthesis of the ligand, see: Kim et al. (2008). For related structures, see: Kim et al. (2007). For distorted trigonal-pyramidal structures of Ni(II) complexes, see: Cho et al. (2007). For thepotential applications of coordination polymers, see: Young & Hanton (2008).

Experimental top

The title compound was synthesized by self-assembly of stoichiometric amounts of silver nitrate and the bctmb ligands in acetonitrile (Kim et al., 2007). Single crystals suitable for X-ray analysis were obtained by evaporation of a solution of the title compound in acetonitrile.

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound, showing displacement ellipsoids drawn at the 30% probability level. All H atoms have been omitted for clarity.
	Fig. 2. Two-dimensional network structure showing C—H···O interactions. All H atoms except those relating C—H···O interactions have been omitted for clarity. [Symmetry codes: (i) x-1, -y+1/2, z-1/2; (ii) x-1, y, z; (iii) x, -y+1/2, z-1/2.]

Phyllo-poly[[µ₂-1,4-bis(cyclohexylsulfanylmethyl)benzene- κ²S:S'](µ₂-nitrato-κ²O:O')silver(I)] top

Crystal data top

[Ag(NO₃)(C₂₀H₃₀S₂)]	F(000) = 1040
M_r = 504.44	D_x = 1.555 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4031 reflections
a = 12.1053 (6) Å	θ = 2.6–27.6°
b = 20.719 (1) Å	µ = 1.15 mm⁻¹
c = 8.5973 (4) Å	T = 173 K
β = 92.256 (1)°	Plate, colorless
V = 2154.61 (18) Å³	0.30 × 0.20 × 0.10 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	4804 independent reflections
Radiation source: fine-focus sealed tube	3174 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.3°, θ_min = 1.7°
ϕ and ω scans	h = −12→15
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −26→23
T_min = 0.724, T_max = 0.894	l = −11→9
13362 measured reflections

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.115	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0558P)² + 0.7474P] where P = (F_o² + 2F_c²)/3
4804 reflections	(Δ/σ)_max = 0.001
238 parameters	Δρ_max = 0.90 e Å⁻³
0 restraints	Δρ_min = −1.00 e Å⁻³

Crystal data top

[Ag(NO₃)(C₂₀H₃₀S₂)]	V = 2154.61 (18) Å³
M_r = 504.44	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.1053 (6) Å	µ = 1.15 mm⁻¹
b = 20.719 (1) Å	T = 173 K
c = 8.5973 (4) Å	0.30 × 0.20 × 0.10 mm
β = 92.256 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4804 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3174 reflections with I > 2σ(I)
T_min = 0.724, T_max = 0.894	R_int = 0.042
13362 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.115	H-atom parameters constrained
S = 1.04	Δρ_max = 0.90 e Å⁻³
4804 reflections	Δρ_min = −1.00 e Å⁻³
238 parameters

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.

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 > 2sigma(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	0.60132 (3)	0.147912 (17)	0.59553 (4)	0.03340 (12)
S1	0.40490 (8)	0.10911 (5)	0.59796 (11)	0.0245 (2)
S2	−0.20353 (9)	0.11318 (6)	0.59401 (12)	0.0332 (3)
O1	0.5747 (3)	0.16475 (16)	0.8814 (4)	0.0538 (10)
O2	0.5492 (4)	0.2420 (2)	1.0367 (7)	0.1033 (19)
O3	0.6861 (4)	0.2458 (2)	0.9036 (6)	0.1007 (19)
N1	0.6032 (3)	0.2176 (2)	0.9376 (4)	0.0391 (7)
C1	0.3798 (4)	0.1476 (2)	0.2840 (5)	0.0330 (10)
H1A	0.4608	0.1544	0.2867	0.040*
H1B	0.3442	0.1886	0.3135	0.040*
C2	0.3396 (4)	0.1280 (2)	0.1194 (5)	0.0371 (11)
H2A	0.2579	0.1249	0.1154	0.044*
H2B	0.3608	0.1618	0.0449	0.044*
C3	0.3879 (4)	0.0640 (2)	0.0714 (5)	0.0381 (11)
H3A	0.4691	0.0682	0.0658	0.046*
H3B	0.3577	0.0522	−0.0335	0.046*
C4	0.3611 (4)	0.0111 (2)	0.1862 (5)	0.0376 (11)
H4A	0.3976	−0.0295	0.1561	0.045*
H4B	0.2802	0.0036	0.1834	0.045*
C5	0.4004 (4)	0.0300 (2)	0.3512 (5)	0.0318 (10)
H5A	0.4821	0.0330	0.3564	0.038*
H5B	0.3784	−0.0040	0.4250	0.038*
C6	0.3511 (3)	0.09466 (19)	0.3992 (4)	0.0236 (9)
H6	0.2688	0.0903	0.4004	0.028*
C7	0.3416 (3)	0.1852 (2)	0.6496 (5)	0.0250 (9)
H7A	0.3716	0.1986	0.7534	0.030*
H7B	0.3629	0.2185	0.5737	0.030*
C8	0.2171 (3)	0.1830 (2)	0.6532 (4)	0.0242 (9)
C9	0.1638 (4)	0.1424 (2)	0.7516 (5)	0.0341 (10)
H9	0.2063	0.1134	0.8153	0.041*
C10	0.0497 (4)	0.1424 (2)	0.7606 (5)	0.0346 (10)
H10	0.0150	0.1137	0.8297	0.041*
C11	−0.0144 (3)	0.1847 (2)	0.6682 (5)	0.0312 (10)
C12	0.0387 (4)	0.2255 (2)	0.5700 (5)	0.0347 (11)
H12	−0.0035	0.2547	0.5068	0.042*
C13	0.1531 (3)	0.2248 (2)	0.5610 (5)	0.0303 (10)
H13	0.1878	0.2531	0.4913	0.036*
C14	−0.1381 (3)	0.1853 (2)	0.6764 (5)	0.0393 (12)
H14A	−0.1676	0.2237	0.6200	0.047*
H14B	−0.1579	0.1894	0.7867	0.047*
C15	−0.1609 (4)	0.1157 (2)	0.3921 (5)	0.0313 (10)
H15	−0.1399	0.1611	0.3665	0.038*
C16	−0.0612 (4)	0.0726 (3)	0.3729 (5)	0.0459 (13)
H16A	−0.0793	0.0282	0.4058	0.055*
H16B	0.0009	0.0884	0.4410	0.055*
C17	−0.0258 (4)	0.0716 (3)	0.2038 (6)	0.0602 (16)
H17A	−0.0005	0.1151	0.1737	0.072*
H17B	0.0365	0.0411	0.1935	0.072*
C18	−0.1225 (4)	0.0509 (3)	0.0960 (5)	0.0504 (14)
H18A	−0.0999	0.0524	−0.0133	0.060*
H18B	−0.1433	0.0059	0.1200	0.060*
C19	−0.2211 (4)	0.0948 (2)	0.1153 (5)	0.0391 (7)
H19A	−0.2018	0.1392	0.0838	0.047*
H19B	−0.2834	0.0798	0.0464	0.047*
C20	−0.2563 (4)	0.0952 (3)	0.2821 (5)	0.0435 (12)
H20A	−0.2815	0.0515	0.3110	0.052*
H20B	−0.3191	0.1253	0.2924	0.052*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.01609 (16)	0.0475 (2)	0.0365 (2)	0.00432 (16)	0.00031 (12)	−0.00270 (17)
S1	0.0197 (5)	0.0337 (6)	0.0199 (5)	0.0066 (4)	−0.0015 (4)	−0.0037 (4)
S2	0.0194 (5)	0.0523 (7)	0.0277 (6)	0.0080 (5)	−0.0005 (4)	−0.0018 (5)
O1	0.083 (3)	0.046 (2)	0.0318 (19)	−0.010 (2)	−0.0063 (18)	−0.0079 (16)
O2	0.092 (3)	0.066 (3)	0.159 (5)	−0.026 (3)	0.093 (4)	−0.053 (3)
O3	0.091 (4)	0.072 (3)	0.146 (5)	−0.035 (3)	0.089 (3)	−0.039 (3)
N1	0.0396 (18)	0.0507 (19)	0.0266 (15)	0.0039 (16)	−0.0033 (13)	−0.0020 (14)
C1	0.040 (3)	0.031 (2)	0.028 (2)	0.009 (2)	0.0021 (19)	0.0002 (19)
C2	0.047 (3)	0.040 (3)	0.024 (2)	0.008 (2)	−0.004 (2)	0.0021 (19)
C3	0.040 (3)	0.050 (3)	0.024 (2)	0.006 (2)	−0.0027 (19)	0.002 (2)
C4	0.051 (3)	0.039 (3)	0.022 (2)	0.004 (2)	−0.010 (2)	−0.0053 (19)
C5	0.037 (3)	0.035 (2)	0.023 (2)	0.008 (2)	−0.0049 (18)	−0.0047 (18)
C6	0.0213 (19)	0.035 (2)	0.0139 (18)	0.0029 (18)	−0.0040 (15)	−0.0016 (17)
C7	0.0176 (19)	0.032 (2)	0.026 (2)	0.0067 (18)	0.0010 (16)	−0.0058 (18)
C8	0.020 (2)	0.035 (2)	0.0176 (19)	0.0045 (18)	0.0006 (15)	−0.0057 (17)
C9	0.028 (2)	0.054 (3)	0.020 (2)	0.005 (2)	−0.0042 (17)	0.002 (2)
C10	0.025 (2)	0.056 (3)	0.022 (2)	0.002 (2)	0.0025 (17)	0.003 (2)
C11	0.018 (2)	0.053 (3)	0.023 (2)	0.006 (2)	−0.0013 (16)	−0.013 (2)
C12	0.028 (2)	0.041 (3)	0.034 (2)	0.014 (2)	−0.0082 (19)	−0.003 (2)
C13	0.028 (2)	0.036 (2)	0.027 (2)	0.007 (2)	0.0044 (18)	0.0048 (19)
C14	0.020 (2)	0.059 (3)	0.039 (3)	0.008 (2)	0.0005 (19)	−0.019 (2)
C15	0.027 (2)	0.040 (3)	0.028 (2)	0.001 (2)	0.0035 (18)	0.0017 (19)
C16	0.036 (3)	0.066 (4)	0.036 (3)	0.017 (3)	0.001 (2)	−0.012 (2)
C17	0.041 (3)	0.090 (4)	0.050 (3)	0.008 (3)	0.021 (3)	−0.016 (3)
C18	0.061 (4)	0.063 (3)	0.028 (3)	−0.007 (3)	0.011 (2)	−0.011 (2)
C19	0.0396 (18)	0.0507 (19)	0.0266 (15)	0.0039 (16)	−0.0033 (13)	−0.0020 (14)
C20	0.031 (3)	0.064 (3)	0.035 (3)	0.008 (2)	−0.004 (2)	−0.008 (2)

Geometric parameters (Å, º) top

Ag1—O2ⁱ	2.415 (4)	C7—H7B	0.9900
Ag1—S2ⁱⁱ	2.4699 (11)	C8—C9	1.371 (6)
Ag1—S1	2.5108 (11)	C8—C13	1.389 (5)
Ag1—O1	2.516 (3)	C9—C10	1.387 (6)
S1—C7	1.816 (4)	C9—H9	0.9500
S1—C6	1.829 (3)	C10—C11	1.397 (6)
S2—C14	1.822 (5)	C10—H10	0.9500
S2—C15	1.831 (4)	C11—C12	1.372 (6)
S2—Ag1ⁱⁱⁱ	2.4699 (11)	C11—C14	1.503 (5)
O1—N1	1.241 (5)	C12—C13	1.390 (6)
O2—N1	1.205 (5)	C12—H12	0.9500
O2—Ag1^iv	2.415 (4)	C13—H13	0.9500
O3—N1	1.207 (5)	C14—H14A	0.9900
C1—C6	1.527 (6)	C14—H14B	0.9900
C1—C2	1.532 (6)	C15—C16	1.515 (6)
C1—H1A	0.9900	C15—C20	1.524 (6)
C1—H1B	0.9900	C15—H15	1.0000
C2—C3	1.513 (6)	C16—C17	1.532 (7)
C2—H2A	0.9900	C16—H16A	0.9900
C2—H2B	0.9900	C16—H16B	0.9900
C3—C4	1.519 (6)	C17—C18	1.525 (7)
C3—H3A	0.9900	C17—H17A	0.9900
C3—H3B	0.9900	C17—H17B	0.9900
C4—C5	1.529 (5)	C18—C19	1.515 (7)
C4—H4A	0.9900	C18—H18A	0.9900
C4—H4B	0.9900	C18—H18B	0.9900
C5—C6	1.531 (6)	C19—C20	1.512 (6)
C5—H5A	0.9900	C19—H19A	0.9900
C5—H5B	0.9900	C19—H19B	0.9900
C6—H6	1.0000	C20—H20A	0.9900
C7—C8	1.510 (5)	C20—H20B	0.9900
C7—H7A	0.9900

O2ⁱ—Ag1—S2ⁱⁱ	121.08 (12)	C9—C8—C7	121.7 (4)
O2ⁱ—Ag1—S1	93.69 (12)	C13—C8—C7	120.2 (4)
S2ⁱⁱ—Ag1—S1	144.39 (4)	C8—C9—C10	121.8 (4)
O2ⁱ—Ag1—O1	91.78 (15)	C8—C9—H9	119.1
S2ⁱⁱ—Ag1—O1	101.83 (10)	C10—C9—H9	119.1
S1—Ag1—O1	83.01 (9)	C9—C10—C11	120.0 (4)
C7—S1—C6	103.42 (18)	C9—C10—H10	120.0
C7—S1—Ag1	97.63 (13)	C11—C10—H10	120.0
C6—S1—Ag1	110.32 (14)	C12—C11—C10	118.3 (4)
C14—S2—C15	102.2 (2)	C12—C11—C14	121.0 (4)
C14—S2—Ag1ⁱⁱⁱ	99.21 (14)	C10—C11—C14	120.7 (4)
C15—S2—Ag1ⁱⁱⁱ	107.56 (14)	C11—C12—C13	121.3 (4)
N1—O1—Ag1	117.3 (3)	C11—C12—H12	119.4
N1—O2—Ag1^iv	113.5 (3)	C13—C12—H12	119.4
O2—N1—O3	116.7 (4)	C8—C13—C12	120.6 (4)
O2—N1—O1	119.6 (5)	C8—C13—H13	119.7
O3—N1—O1	123.6 (5)	C12—C13—H13	119.7
C6—C1—C2	109.7 (3)	C11—C14—S2	113.2 (3)
C6—C1—H1A	109.7	C11—C14—H14A	108.9
C2—C1—H1A	109.7	S2—C14—H14A	108.9
C6—C1—H1B	109.7	C11—C14—H14B	108.9
C2—C1—H1B	109.7	S2—C14—H14B	108.9
H1A—C1—H1B	108.2	H14A—C14—H14B	107.8
C3—C2—C1	111.8 (3)	C16—C15—C20	110.8 (4)
C3—C2—H2A	109.3	C16—C15—S2	109.9 (3)
C1—C2—H2A	109.3	C20—C15—S2	110.2 (3)
C3—C2—H2B	109.3	C16—C15—H15	108.6
C1—C2—H2B	109.3	C20—C15—H15	108.6
H2A—C2—H2B	107.9	S2—C15—H15	108.6
C2—C3—C4	111.1 (4)	C15—C16—C17	111.4 (4)
C2—C3—H3A	109.4	C15—C16—H16A	109.3
C4—C3—H3A	109.4	C17—C16—H16A	109.3
C2—C3—H3B	109.4	C15—C16—H16B	109.3
C4—C3—H3B	109.4	C17—C16—H16B	109.3
H3A—C3—H3B	108.0	H16A—C16—H16B	108.0
C3—C4—C5	110.6 (4)	C18—C17—C16	110.1 (4)
C3—C4—H4A	109.5	C18—C17—H17A	109.6
C5—C4—H4A	109.5	C16—C17—H17A	109.6
C3—C4—H4B	109.5	C18—C17—H17B	109.6
C5—C4—H4B	109.5	C16—C17—H17B	109.6
H4A—C4—H4B	108.1	H17A—C17—H17B	108.1
C4—C5—C6	111.3 (3)	C19—C18—C17	110.7 (4)
C4—C5—H5A	109.4	C19—C18—H18A	109.5
C6—C5—H5A	109.4	C17—C18—H18A	109.5
C4—C5—H5B	109.4	C19—C18—H18B	109.5
C6—C5—H5B	109.4	C17—C18—H18B	109.5
H5A—C5—H5B	108.0	H18A—C18—H18B	108.1
C1—C6—C5	110.7 (3)	C20—C19—C18	111.1 (4)
C1—C6—S1	114.0 (3)	C20—C19—H19A	109.4
C5—C6—S1	105.5 (2)	C18—C19—H19A	109.4
C1—C6—H6	108.9	C20—C19—H19B	109.4
C5—C6—H6	108.9	C18—C19—H19B	109.4
S1—C6—H6	108.9	H19A—C19—H19B	108.0
C8—C7—S1	114.2 (3)	C19—C20—C15	110.8 (4)
C8—C7—H7A	108.7	C19—C20—H20A	109.5
S1—C7—H7A	108.7	C15—C20—H20A	109.5
C8—C7—H7B	108.7	C19—C20—H20B	109.5
S1—C7—H7B	108.7	C15—C20—H20B	109.5
H7A—C7—H7B	107.6	H20A—C20—H20B	108.1
C9—C8—C13	118.0 (4)

O2ⁱ—Ag1—S1—C7	−26.26 (19)	S1—C7—C8—C13	−122.8 (4)
S2ⁱⁱ—Ag1—S1—C7	165.66 (14)	C13—C8—C9—C10	−0.1 (6)
O1—Ag1—S1—C7	65.08 (15)	C7—C8—C9—C10	176.8 (4)
O2ⁱ—Ag1—S1—C6	81.2 (2)	C8—C9—C10—C11	−0.2 (7)
S2ⁱⁱ—Ag1—S1—C6	−86.92 (15)	C9—C10—C11—C12	0.0 (6)
O1—Ag1—S1—C6	172.50 (16)	C9—C10—C11—C14	179.9 (4)
O2ⁱ—Ag1—O1—N1	−38.0 (4)	C10—C11—C12—C13	0.4 (6)
S2ⁱⁱ—Ag1—O1—N1	84.3 (3)	C14—C11—C12—C13	−179.5 (4)
S1—Ag1—O1—N1	−131.5 (3)	C9—C8—C13—C12	0.5 (6)
Ag1^iv—O2—N1—O3	13.2 (7)	C7—C8—C13—C12	−176.4 (4)
Ag1^iv—O2—N1—O1	−169.9 (3)	C11—C12—C13—C8	−0.7 (7)
Ag1—O1—N1—O2	142.9 (5)	C12—C11—C14—S2	110.0 (4)
Ag1—O1—N1—O3	−40.4 (6)	C10—C11—C14—S2	−69.9 (5)
C6—C1—C2—C3	−56.9 (5)	C15—S2—C14—C11	−60.3 (4)
C1—C2—C3—C4	56.7 (5)	Ag1ⁱⁱⁱ—S2—C14—C11	−170.6 (3)
C2—C3—C4—C5	−55.6 (5)	C14—S2—C15—C16	97.4 (4)
C3—C4—C5—C6	55.9 (5)	Ag1ⁱⁱⁱ—S2—C15—C16	−158.7 (3)
C2—C1—C6—C5	56.5 (4)	C14—S2—C15—C20	−140.2 (3)
C2—C1—C6—S1	175.2 (3)	Ag1ⁱⁱⁱ—S2—C15—C20	−36.3 (4)
C4—C5—C6—C1	−56.9 (5)	C20—C15—C16—C17	55.8 (6)
C4—C5—C6—S1	179.4 (3)	S2—C15—C16—C17	177.9 (4)
C7—S1—C6—C1	59.5 (3)	C15—C16—C17—C18	−56.0 (6)
Ag1—S1—C6—C1	−44.0 (3)	C16—C17—C18—C19	56.5 (6)
C7—S1—C6—C5	−178.9 (3)	C17—C18—C19—C20	−57.6 (6)
Ag1—S1—C6—C5	77.6 (3)	C18—C19—C20—C15	57.1 (6)
C6—S1—C7—C8	63.2 (3)	C16—C15—C20—C19	−56.1 (6)
Ag1—S1—C7—C8	176.3 (3)	S2—C15—C20—C19	−178.0 (3)
S1—C7—C8—C9	60.3 (5)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···O3^v	0.99	2.60	3.416 (7)	140
C14—H14B···O3ⁱⁱⁱ	0.99	2.47	3.199 (6)	130
C7—H7B···O2ⁱ	0.99	2.43	3.118 (6)	126

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

Experimental details

Crystal data
Chemical formula	[Ag(NO₃)(C₂₀H₃₀S₂)]
M_r	504.44
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	12.1053 (6), 20.719 (1), 8.5973 (4)
β (°)	92.256 (1)
V (Å³)	2154.61 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.15
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.724, 0.894
No. of measured, independent and observed [I > 2σ(I)] reflections	13362, 4804, 3174
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.644

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.115, 1.04
No. of reflections	4804
No. of parameters	238
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.90, −1.00

Computer programs: SMART (Bruker, 2000), SAINT-Plus (Bruker, 2000), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···O3ⁱ	0.99	2.60	3.416 (7)	140.3
C14—H14B···O3ⁱⁱ	0.99	2.47	3.199 (6)	130.4
C7—H7B···O2ⁱⁱⁱ	0.99	2.43	3.118 (6)	125.9

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

Acknowledgements

This work was supported by Gyeongsang National University. The Korea Research Foundation (KRF-2007–357-C00056) is acknowledged by THK for support.

References

Bruker. (2000). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cho, J., Yap, G. P. A. & Riordan, C. G. (2007). Inorg. Chem. 46, 11308–11315. Web of Science CSD CrossRef PubMed CAS Google Scholar
Kim, T. H., Park, G., Shin, Y. W., Park, K.-M., Choi, M. Y. & Kim, J. (2008). Bull. Korean Chem. Soc. 29, 499–502. CAS Google Scholar
Kim, T. H., Seo, J., Park, K.-M., Lee, S. S. & Kim, J. (2007). Inorg. Chem. Commun. 10, 313-317. Web of Science 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
Young, A. G. & Hanton, L. R. (2008). Coord. Chem. Rev. 252, 1346–1386. Web of Science 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.