Phyllo-poly[[μ(2)-1,4-bis-(cyclo-hexyl-sulfanylmeth-yl)benzene-κS:S'](μ(2)-nitrato-κO:O')silver(I)].

The title compound, [Ag(NO(3))(C(20)H(30)S(2))](n), was synthesized by the reaction of silver nitrate and 1,4-bis-(cyclo-hexyl-thio-meth-yl)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 = 504.44

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.115

S = 1.04

4804 reflections

238 parameters

H-atom parameters constrained

Δρmax = 0.90 e Å−3

Δρmin = −1.00 e Å−3

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.

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

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

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

[Ag(NO3)(C20H30S2)]	F(000) = 1040
Mr = 504.44	Dx = 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

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

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(Fo2) + (0.0558P)2 + 0.7474P] where P = (Fo2 + 2Fc2)/3
4804 reflections	(Δ/σ)max = 0.001
238 parameters	Δρmax = 0.90 e Å−3
0 restraints	Δρmin = −1.00 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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—Ag1iv	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—Ag1iv	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)
Ag1iv—O2—N1—O3	13.2 (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—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)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···O3v	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

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) ; (ii) ; (iii) .