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Acta Cryst. (2009). E65, m385    [ doi:10.1107/S1600536809007910 ]

Phyllo-poly[[[mu]2-1,4-bis(cyclohexylsulfanylmethyl)benzene-[kappa]2S:S']([mu]2-nitrato-[kappa]2O:O')silver(I)]

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

Abstract top

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; AgI 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.

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 AgI 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.

Refinement top

All H-atoms were positioned geometrically and refined using a riding model with d(C—H) = 0.93 Å, Uiso =1.2Ueq(C) for aromatic and 0.97 Å, Uiso = 1.2Ueq(C) for CH2 atoms.

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
[Figure 1] 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.
[Figure 2] 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
Mr = 504.44Dx = 1.555 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4031 reflections
a = 12.1053 (6) Åθ = 2.6–27.6°
b = 20.719 (1) ŵ = 1.15 mm−1
c = 8.5973 (4) ÅT = 173 K
β = 92.256 (1)°Plate, colorless
V = 2154.61 (18) Å30.30 × 0.20 × 0.10 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer		4804 independent reflections
Radiation source: fine-focus sealed tube3174 reflections with I > 2σ(I)
graphiteRint = 0.042
Detector resolution: 10.0 pixels mm-1θmax = 27.3°, θmin = 1.7°
φ and ω scansh = −12→15
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		k = −26→23
Tmin = 0.724, Tmax = 0.894l = −11→9
13362 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0558P)2 + 0.7474P]
where P = (Fo2 + 2Fc2)/3
4804 reflections(Δ/σ)max = 0.001
238 parametersΔρmax = 0.90 e Å−3
0 restraintsΔρmin = −1.00 e Å−3
Crystal data top
[Ag(NO3)(C20H30S2)]V = 2154.61 (18) Å3
Mr = 504.44Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.1053 (6) ŵ = 1.15 mm−1
b = 20.719 (1) ÅT = 173 K
c = 8.5973 (4) Å0.30 × 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)
Tmin = 0.724, Tmax = 0.894Rint = 0.042
13362 measured reflectionsθmax = 27.3°
Refinement top
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.115Δρmax = 0.90 e Å−3
S = 1.04Δρmin = −1.00 e Å−3
4804 reflectionsAbsolute structure: ?
238 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
xyzUiso*/Ueq
Ag10.60132 (3)0.147912 (17)0.59553 (4)0.03340 (12)
S10.40490 (8)0.10911 (5)0.59796 (11)0.0245 (2)
S2−0.20353 (9)0.11318 (6)0.59401 (12)0.0332 (3)
O10.5747 (3)0.16475 (16)0.8814 (4)0.0538 (10)
O20.5492 (4)0.2420 (2)1.0367 (7)0.1033 (19)
O30.6861 (4)0.2458 (2)0.9036 (6)0.1007 (19)
N10.6032 (3)0.2176 (2)0.9376 (4)0.0391 (7)
C10.3798 (4)0.1476 (2)0.2840 (5)0.0330 (10)
H1A0.46080.15440.28670.040*
H1B0.34420.18860.31350.040*
C20.3396 (4)0.1280 (2)0.1194 (5)0.0371 (11)
H2A0.25790.12490.11540.044*
H2B0.36080.16180.04490.044*
C30.3879 (4)0.0640 (2)0.0714 (5)0.0381 (11)
H3A0.46910.06820.06580.046*
H3B0.35770.0522−0.03350.046*
C40.3611 (4)0.0111 (2)0.1862 (5)0.0376 (11)
H4A0.3976−0.02950.15610.045*
H4B0.28020.00360.18340.045*
C50.4004 (4)0.0300 (2)0.3512 (5)0.0318 (10)
H5A0.48210.03300.35640.038*
H5B0.3784−0.00400.42500.038*
C60.3511 (3)0.09466 (19)0.3992 (4)0.0236 (9)
H60.26880.09030.40040.028*
C70.3416 (3)0.1852 (2)0.6496 (5)0.0250 (9)
H7A0.37160.19860.75340.030*
H7B0.36290.21850.57370.030*
C80.2171 (3)0.1830 (2)0.6532 (4)0.0242 (9)
C90.1638 (4)0.1424 (2)0.7516 (5)0.0341 (10)
H90.20630.11340.81530.041*
C100.0497 (4)0.1424 (2)0.7606 (5)0.0346 (10)
H100.01500.11370.82970.041*
C11−0.0144 (3)0.1847 (2)0.6682 (5)0.0312 (10)
C120.0387 (4)0.2255 (2)0.5700 (5)0.0347 (11)
H12−0.00350.25470.50680.042*
C130.1531 (3)0.2248 (2)0.5610 (5)0.0303 (10)
H130.18780.25310.49130.036*
C14−0.1381 (3)0.1853 (2)0.6764 (5)0.0393 (12)
H14A−0.16760.22370.62000.047*
H14B−0.15790.18940.78670.047*
C15−0.1609 (4)0.1157 (2)0.3921 (5)0.0313 (10)
H15−0.13990.16110.36650.038*
C16−0.0612 (4)0.0726 (3)0.3729 (5)0.0459 (13)
H16A−0.07930.02820.40580.055*
H16B0.00090.08840.44100.055*
C17−0.0258 (4)0.0716 (3)0.2038 (6)0.0602 (16)
H17A−0.00050.11510.17370.072*
H17B0.03650.04110.19350.072*
C18−0.1225 (4)0.0509 (3)0.0960 (5)0.0504 (14)
H18A−0.09990.0524−0.01330.060*
H18B−0.14330.00590.12000.060*
C19−0.2211 (4)0.0948 (2)0.1153 (5)0.0391 (7)
H19A−0.20180.13920.08380.047*
H19B−0.28340.07980.04640.047*
C20−0.2563 (4)0.0952 (3)0.2821 (5)0.0435 (12)
H20A−0.28150.05150.31100.052*
H20B−0.31910.12530.29240.052*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ag10.01609 (16)0.0475 (2)0.0365 (2)0.00432 (16)0.00031 (12)−0.00270 (17)
S10.0197 (5)0.0337 (6)0.0199 (5)0.0066 (4)−0.0015 (4)−0.0037 (4)
S20.0194 (5)0.0523 (7)0.0277 (6)0.0080 (5)−0.0005 (4)−0.0018 (5)
O10.083 (3)0.046 (2)0.0318 (19)−0.010 (2)−0.0063 (18)−0.0079 (16)
O20.092 (3)0.066 (3)0.159 (5)−0.026 (3)0.093 (4)−0.053 (3)
O30.091 (4)0.072 (3)0.146 (5)−0.035 (3)0.089 (3)−0.039 (3)
N10.0396 (18)0.0507 (19)0.0266 (15)0.0039 (16)−0.0033 (13)−0.0020 (14)
C10.040 (3)0.031 (2)0.028 (2)0.009 (2)0.0021 (19)0.0002 (19)
C20.047 (3)0.040 (3)0.024 (2)0.008 (2)−0.004 (2)0.0021 (19)
C30.040 (3)0.050 (3)0.024 (2)0.006 (2)−0.0027 (19)0.002 (2)
C40.051 (3)0.039 (3)0.022 (2)0.004 (2)−0.010 (2)−0.0053 (19)
C50.037 (3)0.035 (2)0.023 (2)0.008 (2)−0.0049 (18)−0.0047 (18)
C60.0213 (19)0.035 (2)0.0139 (18)0.0029 (18)−0.0040 (15)−0.0016 (17)
C70.0176 (19)0.032 (2)0.026 (2)0.0067 (18)0.0010 (16)−0.0058 (18)
C80.020 (2)0.035 (2)0.0176 (19)0.0045 (18)0.0006 (15)−0.0057 (17)
C90.028 (2)0.054 (3)0.020 (2)0.005 (2)−0.0042 (17)0.002 (2)
C100.025 (2)0.056 (3)0.022 (2)0.002 (2)0.0025 (17)0.003 (2)
C110.018 (2)0.053 (3)0.023 (2)0.006 (2)−0.0013 (16)−0.013 (2)
C120.028 (2)0.041 (3)0.034 (2)0.014 (2)−0.0082 (19)−0.003 (2)
C130.028 (2)0.036 (2)0.027 (2)0.007 (2)0.0044 (18)0.0048 (19)
C140.020 (2)0.059 (3)0.039 (3)0.008 (2)0.0005 (19)−0.019 (2)
C150.027 (2)0.040 (3)0.028 (2)0.001 (2)0.0035 (18)0.0017 (19)
C160.036 (3)0.066 (4)0.036 (3)0.017 (3)0.001 (2)−0.012 (2)
C170.041 (3)0.090 (4)0.050 (3)0.008 (3)0.021 (3)−0.016 (3)
C180.061 (4)0.063 (3)0.028 (3)−0.007 (3)0.011 (2)−0.011 (2)
C190.0396 (18)0.0507 (19)0.0266 (15)0.0039 (16)−0.0033 (13)−0.0020 (14)
C200.031 (3)0.064 (3)0.035 (3)0.008 (2)−0.004 (2)−0.008 (2)
Geometric parameters (Å, °) top
Ag1—O2i2.415 (4)C7—H7B0.9900
Ag1—S2ii2.4699 (11)C8—C91.371 (6)
Ag1—S12.5108 (11)C8—C131.389 (5)
Ag1—O12.516 (3)C9—C101.387 (6)
S1—C71.816 (4)C9—H90.9500
S1—C61.829 (3)C10—C111.397 (6)
S2—C141.822 (5)C10—H100.9500
S2—C151.831 (4)C11—C121.372 (6)
S2—Ag1iii2.4699 (11)C11—C141.503 (5)
O1—N11.241 (5)C12—C131.390 (6)
O2—N11.205 (5)C12—H120.9500
O2—Ag1iv2.415 (4)C13—H130.9500
O3—N11.207 (5)C14—H14A0.9900
C1—C61.527 (6)C14—H14B0.9900
C1—C21.532 (6)C15—C161.515 (6)
C1—H1A0.9900C15—C201.524 (6)
C1—H1B0.9900C15—H151.0000
C2—C31.513 (6)C16—C171.532 (7)
C2—H2A0.9900C16—H16A0.9900
C2—H2B0.9900C16—H16B0.9900
C3—C41.519 (6)C17—C181.525 (7)
C3—H3A0.9900C17—H17A0.9900
C3—H3B0.9900C17—H17B0.9900
C4—C51.529 (5)C18—C191.515 (7)
C4—H4A0.9900C18—H18A0.9900
C4—H4B0.9900C18—H18B0.9900
C5—C61.531 (6)C19—C201.512 (6)
C5—H5A0.9900C19—H19A0.9900
C5—H5B0.9900C19—H19B0.9900
C6—H61.0000C20—H20A0.9900
C7—C81.510 (5)C20—H20B0.9900
C7—H7A0.9900
O2i—Ag1—S2ii121.08 (12)C9—C8—C7121.7 (4)
O2i—Ag1—S193.69 (12)C13—C8—C7120.2 (4)
S2ii—Ag1—S1144.39 (4)C8—C9—C10121.8 (4)
O2i—Ag1—O191.78 (15)C8—C9—H9119.1
S2ii—Ag1—O1101.83 (10)C10—C9—H9119.1
S1—Ag1—O183.01 (9)C9—C10—C11120.0 (4)
C7—S1—C6103.42 (18)C9—C10—H10120.0
C7—S1—Ag197.63 (13)C11—C10—H10120.0
C6—S1—Ag1110.32 (14)C12—C11—C10118.3 (4)
C14—S2—C15102.2 (2)C12—C11—C14121.0 (4)
C14—S2—Ag1iii99.21 (14)C10—C11—C14120.7 (4)
C15—S2—Ag1iii107.56 (14)C11—C12—C13121.3 (4)
N1—O1—Ag1117.3 (3)C11—C12—H12119.4
N1—O2—Ag1iv113.5 (3)C13—C12—H12119.4
O2—N1—O3116.7 (4)C8—C13—C12120.6 (4)
O2—N1—O1119.6 (5)C8—C13—H13119.7
O3—N1—O1123.6 (5)C12—C13—H13119.7
C6—C1—C2109.7 (3)C11—C14—S2113.2 (3)
C6—C1—H1A109.7C11—C14—H14A108.9
C2—C1—H1A109.7S2—C14—H14A108.9
C6—C1—H1B109.7C11—C14—H14B108.9
C2—C1—H1B109.7S2—C14—H14B108.9
H1A—C1—H1B108.2H14A—C14—H14B107.8
C3—C2—C1111.8 (3)C16—C15—C20110.8 (4)
C3—C2—H2A109.3C16—C15—S2109.9 (3)
C1—C2—H2A109.3C20—C15—S2110.2 (3)
C3—C2—H2B109.3C16—C15—H15108.6
C1—C2—H2B109.3C20—C15—H15108.6
H2A—C2—H2B107.9S2—C15—H15108.6
C2—C3—C4111.1 (4)C15—C16—C17111.4 (4)
C2—C3—H3A109.4C15—C16—H16A109.3
C4—C3—H3A109.4C17—C16—H16A109.3
C2—C3—H3B109.4C15—C16—H16B109.3
C4—C3—H3B109.4C17—C16—H16B109.3
H3A—C3—H3B108.0H16A—C16—H16B108.0
C3—C4—C5110.6 (4)C18—C17—C16110.1 (4)
C3—C4—H4A109.5C18—C17—H17A109.6
C5—C4—H4A109.5C16—C17—H17A109.6
C3—C4—H4B109.5C18—C17—H17B109.6
C5—C4—H4B109.5C16—C17—H17B109.6
H4A—C4—H4B108.1H17A—C17—H17B108.1
C4—C5—C6111.3 (3)C19—C18—C17110.7 (4)
C4—C5—H5A109.4C19—C18—H18A109.5
C6—C5—H5A109.4C17—C18—H18A109.5
C4—C5—H5B109.4C19—C18—H18B109.5
C6—C5—H5B109.4C17—C18—H18B109.5
H5A—C5—H5B108.0H18A—C18—H18B108.1
C1—C6—C5110.7 (3)C20—C19—C18111.1 (4)
C1—C6—S1114.0 (3)C20—C19—H19A109.4
C5—C6—S1105.5 (2)C18—C19—H19A109.4
C1—C6—H6108.9C20—C19—H19B109.4
C5—C6—H6108.9C18—C19—H19B109.4
S1—C6—H6108.9H19A—C19—H19B108.0
C8—C7—S1114.2 (3)C19—C20—C15110.8 (4)
C8—C7—H7A108.7C19—C20—H20A109.5
S1—C7—H7A108.7C15—C20—H20A109.5
C8—C7—H7B108.7C19—C20—H20B109.5
S1—C7—H7B108.7C15—C20—H20B109.5
H7A—C7—H7B107.6H20A—C20—H20B108.1
C9—C8—C13118.0 (4)
O2i—Ag1—S1—C7−26.26 (19)S1—C7—C8—C13−122.8 (4)
S2ii—Ag1—S1—C7165.66 (14)C13—C8—C9—C10−0.1 (6)
O1—Ag1—S1—C765.08 (15)C7—C8—C9—C10176.8 (4)
O2i—Ag1—S1—C681.2 (2)C8—C9—C10—C11−0.2 (7)
S2ii—Ag1—S1—C6−86.92 (15)C9—C10—C11—C120.0 (6)
O1—Ag1—S1—C6172.50 (16)C9—C10—C11—C14179.9 (4)
O2i—Ag1—O1—N1−38.0 (4)C10—C11—C12—C130.4 (6)
S2ii—Ag1—O1—N184.3 (3)C14—C11—C12—C13−179.5 (4)
S1—Ag1—O1—N1−131.5 (3)C9—C8—C13—C120.5 (6)
Ag1iv—O2—N1—O313.2 (7)C7—C8—C13—C12−176.4 (4)
Ag1iv—O2—N1—O1−169.9 (3)C11—C12—C13—C8−0.7 (7)
Ag1—O1—N1—O2142.9 (5)C12—C11—C14—S2110.0 (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—C456.7 (5)Ag1iii—S2—C14—C11−170.6 (3)
C2—C3—C4—C5−55.6 (5)C14—S2—C15—C1697.4 (4)
C3—C4—C5—C655.9 (5)Ag1iii—S2—C15—C16−158.7 (3)
C2—C1—C6—C556.5 (4)C14—S2—C15—C20−140.2 (3)
C2—C1—C6—S1175.2 (3)Ag1iii—S2—C15—C20−36.3 (4)
C4—C5—C6—C1−56.9 (5)C20—C15—C16—C1755.8 (6)
C4—C5—C6—S1179.4 (3)S2—C15—C16—C17177.9 (4)
C7—S1—C6—C159.5 (3)C15—C16—C17—C18−56.0 (6)
Ag1—S1—C6—C1−44.0 (3)C16—C17—C18—C1956.5 (6)
C7—S1—C6—C5−178.9 (3)C17—C18—C19—C20−57.6 (6)
Ag1—S1—C6—C577.6 (3)C18—C19—C20—C1557.1 (6)
C6—S1—C7—C863.2 (3)C16—C15—C20—C19−56.1 (6)
Ag1—S1—C7—C8176.3 (3)S2—C15—C20—C19−178.0 (3)
S1—C7—C8—C960.3 (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, °) top
D—H···AD—HH···AD···AD—H···A
C14—H14A···O3v0.992.603.416 (7)140
C14—H14B···O3iii0.992.473.199 (6)130
C7—H7B···O2i0.992.433.118 (6)126
Symmetry codes: (v) x−1, −y+1/2, z−1/2; (iii) x−1, y, z; (i) x, −y+1/2, z−1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C14—H14A···O3i0.992.603.416 (7)140
C14—H14B···O3ii0.992.473.199 (6)130
C7—H7B···O2iii0.992.433.118 (6)126
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 top

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

references
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