catena-Poly[[silver(I)-μ-bis-{2-[(E)-phenyl-diazen-yl]-1H-imidazol-1-yl}methane] trifluoro-methane-sulfonate].

The title compound, {[Ag(C(19)H(16)N(8))](CF(3)SO(3))}(n), is a coordin-ation polymer with cationic chain motif. The Ag(+) cation is coordinated by two unsubstituted imidazolyl N atoms of two independent 2-paBIM ligands [2-paBIM is bis-{2-[(E)-phenyl-diazen-yl]-1H-imidazol-1-yl}methane]. The shortest Ag⋯Ag separation in a cationic chain is 8.841 (2) Å and the dihedral angle between two 2-phenyl-diazenyl-imidazole planes in the same ligand is 74.7 (3)°. Weak C-H⋯O interactions are seen in the crystal.

Related literature

For background to metal-organic frameworks, see: Batten & Robson (1998 ▶); Burrows (2011 ▶); Leininger et al. (2000 ▶); Tanabe & Cohen (2011 ▶). For examples of supra­molecular arrangements using multidentate N-donor spacer ligands, see: Custelcean (2010 ▶); Pschirer et al. (2002 ▶). For structures of related ligands, see: Hamilton & Ziegler (2004 ▶); Jin et al. (2009 ▶).

Experimental

Crystal data

[Ag(C19H16N8)](CF3SO3)

M = 613.34

Orthorhombic,

a = 16.0251 (19) Å

b = 8.455 (1) Å

c = 17.293 (2) Å

V = 2343.0 (5) Å3

Z = 4

Mo Kα radiation

μ = 1.01 mm−1

T = 298 K

0.13 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.879, T max = 0.905

11674 measured reflections

4823 independent reflections

4073 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.167

S = 1.13

4823 reflections

326 parameters

1 restraint

H-atom parameters constrained

Δρmax = 1.08 e Å−3

Δρmin = −0.54 e Å−3

Absolute structure: Flack (1983 ▶), 1807 Friedel pairs

Flack parameter: 0.54 (5)

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811035951/im2314sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811035951/im2314Isup2.hkl

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

[Ag(C19H16N8)](CF3SO3)	F(000) = 1224
Mr = 613.34	Dx = 1.739 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 4016 reflections
a = 16.0251 (19) Å	θ = 2.4–24.4°
b = 8.455 (1) Å	µ = 1.01 mm−1
c = 17.293 (2) Å	T = 298 K
V = 2343.0 (5) Å3	Block, red
Z = 4	0.13 × 0.10 × 0.10 mm

Bruker SMART CCD area-detector diffractometer	4823 independent reflections
Radiation source: fine-focus sealed tube	4073 reflections with I > 2σ(I)
graphite	Rint = 0.057
phi and ω scans	θmax = 28.3°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −21→16
Tmin = 0.879, Tmax = 0.905	k = −11→11
11674 measured reflections	l = −23→19

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)] = 0.065	H-atom parameters constrained
wR(F2) = 0.167	w = 1/[σ2(Fo2) + (0.0908P)2] where P = (Fo2 + 2Fc2)/3
S = 1.13	(Δ/σ)max = 0.023
4823 reflections	Δρmax = 1.08 e Å−3
326 parameters	Δρmin = −0.54 e Å−3
1 restraint	Absolute structure: Flack (1983), 1807 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.54 (5)

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
Ag1	0.47527 (3)	0.90148 (7)	0.39948 (4)	0.0682 (2)
C1	0.3518 (4)	1.2960 (8)	0.3721 (3)	0.0509 (14)
C2	0.3877 (5)	1.3393 (13)	0.4422 (5)	0.078 (2)
H2	0.4239	1.2714	0.4680	0.093*
C3	0.3678 (5)	1.4883 (12)	0.4732 (5)	0.078 (3)
H3	0.3912	1.5201	0.5199	0.094*
C4	0.3152 (6)	1.5845 (10)	0.4357 (6)	0.075 (2)
H4	0.3035	1.6836	0.4563	0.090*
C5	0.2785 (6)	1.5408 (12)	0.3679 (5)	0.078 (2)
H5	0.2411	1.6083	0.3434	0.093*
C6	0.2974 (5)	1.3950 (8)	0.3356 (5)	0.0589 (16)
H6	0.2729	1.3647	0.2892	0.071*
C7	0.3657 (3)	0.9567 (8)	0.2569 (3)	0.0423 (12)
C8	0.3670 (4)	0.7515 (7)	0.1808 (4)	0.0528 (15)
H8	0.3584	0.6836	0.1392	0.063*
C9	0.4113 (4)	0.7196 (8)	0.2445 (4)	0.0541 (15)
H9	0.4383	0.6243	0.2542	0.065*
C10	0.2915 (3)	0.9926 (9)	0.1299 (3)	0.0516 (14)
H10A	0.2600	0.9216	0.0969	0.062*
H10B	0.2523	1.0625	0.1556	0.062*
C11	0.3752 (4)	1.2323 (9)	0.0999 (4)	0.0630 (17)
H11	0.3593	1.2961	0.1412	0.076*
C12	0.4303 (5)	1.2674 (9)	0.0438 (4)	0.0623 (17)
H12	0.4594	1.3623	0.0405	0.075*
C13	0.3883 (3)	1.0371 (8)	0.0180 (3)	0.0445 (13)
C14	0.3903 (4)	0.7183 (8)	−0.1108 (4)	0.0544 (15)
C15	0.4215 (5)	0.7007 (11)	−0.1837 (4)	0.0690 (19)
H15	0.4534	0.7812	−0.2053	0.083*
C16	0.4061 (7)	0.5638 (13)	−0.2260 (6)	0.088 (3)
H16	0.4262	0.5518	−0.2760	0.106*
C17	0.3599 (7)	0.4471 (14)	−0.1909 (7)	0.093 (3)
H17	0.3498	0.3540	−0.2179	0.112*
C18	0.3283 (7)	0.4624 (11)	−0.1177 (6)	0.090 (3)
H18	0.2972	0.3812	−0.0957	0.108*
C19	0.3433 (6)	0.6010 (9)	−0.0767 (5)	0.070 (2)
H19	0.3219	0.6143	−0.0271	0.084*
C20	0.5958 (6)	−0.0608 (11)	0.1501 (5)	0.075 (2)
F1	0.5243 (3)	0.0059 (14)	0.1521 (6)	0.152 (4)
F2	0.5931 (9)	−0.2044 (11)	0.1290 (6)	0.199 (6)
F3	0.6175 (6)	−0.0668 (10)	0.2239 (4)	0.131 (3)
N1	0.3750 (3)	1.1435 (7)	0.3445 (3)	0.0501 (11)
N2	0.3443 (3)	1.1075 (6)	0.2807 (3)	0.0462 (11)
N3	0.4113 (3)	0.8465 (6)	0.2935 (3)	0.0484 (11)
N4	0.3370 (3)	0.9007 (6)	0.1878 (3)	0.0450 (12)
N5	0.3475 (3)	1.0842 (6)	0.0837 (3)	0.0427 (11)
N6	0.4379 (4)	1.1474 (7)	−0.0069 (3)	0.0520 (12)
N7	0.3705 (3)	0.8891 (6)	−0.0124 (3)	0.0465 (12)
N8	0.4090 (3)	0.8640 (7)	−0.0747 (3)	0.0508 (12)
O1	0.6671 (6)	0.1988 (10)	0.1246 (6)	0.127 (3)
O2	0.7448 (5)	−0.0336 (14)	0.1010 (6)	0.149 (4)
O3	0.6378 (5)	0.0472 (10)	0.0180 (4)	0.104 (2)
S1	0.67017 (10)	0.0515 (2)	0.09234 (12)	0.0592 (4)

	U11	U22	U33	U12	U13	U23
Ag1	0.0678 (3)	0.0891 (4)	0.0477 (3)	−0.0057 (2)	−0.0201 (2)	0.0008 (3)
C1	0.047 (3)	0.059 (4)	0.047 (3)	−0.014 (3)	0.013 (2)	−0.013 (3)
C2	0.053 (4)	0.117 (7)	0.064 (5)	−0.010 (4)	0.000 (3)	−0.016 (5)
C3	0.066 (4)	0.104 (7)	0.064 (5)	−0.033 (5)	0.016 (4)	−0.048 (5)
C4	0.079 (6)	0.069 (5)	0.077 (6)	−0.016 (4)	0.024 (5)	−0.027 (4)
C5	0.082 (5)	0.077 (5)	0.074 (5)	0.002 (4)	0.024 (4)	−0.006 (4)
C6	0.063 (4)	0.056 (4)	0.058 (4)	−0.004 (3)	0.012 (3)	−0.006 (3)
C7	0.031 (2)	0.065 (4)	0.032 (3)	−0.006 (2)	0.0032 (19)	0.005 (2)
C8	0.070 (4)	0.045 (3)	0.044 (3)	−0.010 (3)	−0.001 (3)	−0.011 (3)
C9	0.059 (4)	0.044 (3)	0.059 (4)	−0.001 (3)	0.001 (3)	0.002 (3)
C10	0.033 (2)	0.092 (5)	0.030 (3)	0.000 (3)	0.001 (2)	−0.011 (3)
C11	0.058 (4)	0.080 (5)	0.051 (4)	0.010 (3)	0.006 (3)	−0.004 (3)
C12	0.071 (4)	0.058 (4)	0.058 (4)	−0.002 (3)	0.007 (3)	0.006 (3)
C13	0.032 (2)	0.069 (4)	0.033 (3)	0.004 (2)	−0.004 (2)	0.001 (2)
C14	0.057 (3)	0.065 (4)	0.041 (3)	0.013 (3)	−0.007 (3)	−0.006 (3)
C15	0.069 (4)	0.081 (5)	0.056 (4)	0.019 (4)	0.005 (3)	−0.015 (4)
C16	0.084 (6)	0.109 (8)	0.070 (6)	0.020 (5)	−0.004 (5)	−0.017 (5)
C17	0.098 (7)	0.091 (7)	0.090 (7)	0.017 (6)	−0.030 (6)	−0.039 (6)
C18	0.117 (7)	0.063 (5)	0.090 (8)	−0.007 (5)	0.000 (6)	−0.005 (5)
C19	0.085 (5)	0.066 (5)	0.059 (4)	−0.002 (4)	−0.001 (4)	0.000 (3)
C20	0.076 (5)	0.073 (5)	0.076 (6)	−0.010 (4)	0.007 (4)	0.029 (4)
F1	0.051 (3)	0.237 (9)	0.169 (8)	−0.006 (4)	0.022 (3)	0.111 (8)
F2	0.347 (16)	0.110 (5)	0.141 (8)	−0.123 (8)	0.069 (9)	−0.022 (5)
F3	0.159 (7)	0.167 (7)	0.065 (4)	0.015 (5)	0.009 (4)	0.049 (4)
N1	0.050 (3)	0.064 (3)	0.037 (2)	−0.006 (2)	−0.001 (2)	−0.002 (2)
N2	0.043 (2)	0.061 (3)	0.035 (2)	−0.003 (2)	0.0013 (19)	−0.003 (2)
N3	0.050 (3)	0.051 (3)	0.044 (3)	−0.005 (2)	−0.006 (2)	0.006 (2)
N4	0.051 (3)	0.051 (3)	0.033 (2)	−0.008 (2)	0.002 (2)	−0.0095 (19)
N5	0.039 (2)	0.054 (3)	0.035 (2)	0.0043 (18)	−0.0010 (19)	0.001 (2)
N6	0.049 (3)	0.061 (3)	0.047 (3)	0.008 (3)	0.006 (2)	0.008 (3)
N7	0.044 (2)	0.062 (3)	0.034 (2)	0.006 (2)	0.0006 (18)	0.000 (2)
N8	0.051 (3)	0.064 (3)	0.038 (2)	0.009 (2)	0.0003 (19)	0.000 (2)
O1	0.154 (8)	0.089 (5)	0.138 (8)	−0.037 (5)	0.043 (6)	−0.017 (5)
O2	0.076 (4)	0.222 (9)	0.148 (8)	0.060 (6)	0.018 (5)	0.058 (8)
O3	0.120 (6)	0.134 (6)	0.060 (4)	−0.030 (5)	−0.012 (4)	0.037 (4)
S1	0.0443 (7)	0.0712 (10)	0.0622 (10)	−0.0010 (7)	0.0022 (7)	0.0131 (9)

Ag1—N3	2.152 (5)	C11—H11	0.9300
Ag1—N6i	2.174 (6)	C12—N6	1.347 (10)
C1—C6	1.364 (11)	C12—H12	0.9300
C1—C2	1.390 (10)	C13—N6	1.298 (9)
C1—N1	1.424 (9)	C13—N5	1.371 (7)
C2—C3	1.406 (14)	C13—N7	1.387 (8)
C2—H2	0.9300	C14—C15	1.364 (10)
C3—C4	1.339 (14)	C14—C19	1.378 (11)
C3—H3	0.9300	C14—N8	1.413 (8)
C4—C5	1.363 (13)	C15—C16	1.391 (13)
C4—H4	0.9300	C15—H15	0.9300
C5—C6	1.386 (11)	C16—C17	1.374 (16)
C5—H5	0.9300	C16—H16	0.9300
C6—H6	0.9300	C17—C18	1.369 (16)
C7—N3	1.342 (8)	C17—H17	0.9300
C7—N4	1.365 (8)	C18—C19	1.390 (12)
C7—N2	1.383 (8)	C18—H18	0.9300
C8—C9	1.338 (10)	C19—H19	0.9300
C8—N4	1.355 (8)	C20—F2	1.268 (13)
C8—H8	0.9300	C20—F1	1.278 (11)
C9—N3	1.366 (9)	C20—F3	1.322 (11)
C9—H9	0.9300	C20—S1	1.822 (8)
C10—N5	1.429 (8)	N1—N2	1.246 (7)
C10—N4	1.463 (9)	N6—Ag1ii	2.174 (6)
C10—H10A	0.9700	N7—N8	1.259 (7)
C10—H10B	0.9700	O1—S1	1.365 (9)
C11—C12	1.345 (10)	O2—S1	1.404 (7)
C11—N5	1.357 (9)	O3—S1	1.388 (7)
N3—Ag1—N6i	153.9 (2)	C19—C14—N8	123.7 (6)
C6—C1—C2	120.4 (7)	C14—C15—C16	120.8 (9)
C6—C1—N1	124.6 (6)	C14—C15—H15	119.6
C2—C1—N1	115.0 (7)	C16—C15—H15	119.6
C1—C2—C3	118.3 (9)	C17—C16—C15	117.5 (9)
C1—C2—H2	120.8	C17—C16—H16	121.3
C3—C2—H2	120.8	C15—C16—H16	121.3
C4—C3—C2	120.2 (7)	C16—C17—C18	122.6 (9)
C4—C3—H3	119.9	C16—C17—H17	118.7
C2—C3—H3	119.9	C18—C17—H17	118.7
C3—C4—C5	121.6 (8)	C17—C18—C19	119.2 (10)
C3—C4—H4	119.2	C17—C18—H18	120.4
C5—C4—H4	119.2	C19—C18—H18	120.4
C4—C5—C6	119.5 (10)	C14—C19—C18	118.9 (8)
C4—C5—H5	120.2	C14—C19—H19	120.6
C6—C5—H5	120.2	C18—C19—H19	120.6
C1—C6—C5	120.0 (8)	F2—C20—F1	113.5 (11)
C1—C6—H6	120.0	F2—C20—F3	104.5 (10)
C5—C6—H6	120.0	F1—C20—F3	103.1 (9)
N3—C7—N4	110.8 (6)	F2—C20—S1	111.3 (8)
N3—C7—N2	129.4 (6)	F1—C20—S1	111.7 (6)
N4—C7—N2	119.8 (5)	F3—C20—S1	112.2 (7)
C9—C8—N4	107.5 (6)	N2—N1—C1	114.6 (6)
C9—C8—H8	126.2	N1—N2—C7	113.0 (5)
N4—C8—H8	126.2	C7—N3—C9	104.6 (5)
C8—C9—N3	110.7 (6)	C7—N3—Ag1	120.7 (4)
C8—C9—H9	124.7	C9—N3—Ag1	134.2 (4)
N3—C9—H9	124.7	C8—N4—C7	106.4 (6)
N5—C10—N4	110.9 (4)	C8—N4—C10	127.6 (5)
N5—C10—H10A	109.5	C7—N4—C10	125.6 (5)
N4—C10—H10A	109.5	C11—N5—C13	106.4 (5)
N5—C10—H10B	109.5	C11—N5—C10	126.1 (5)
N4—C10—H10B	109.5	C13—N5—C10	127.3 (5)
H10A—C10—H10B	108.0	C13—N6—C12	105.6 (6)
C12—C11—N5	105.6 (6)	C13—N6—Ag1ii	120.2 (5)
C12—C11—H11	127.2	C12—N6—Ag1ii	133.3 (5)
N5—C11—H11	127.2	N8—N7—C13	112.0 (5)
C11—C12—N6	111.3 (7)	N7—N8—C14	114.9 (6)
C11—C12—H12	124.4	O1—S1—O3	112.9 (6)
N6—C12—H12	124.4	O1—S1—O2	117.1 (7)
N6—C13—N5	111.0 (6)	O3—S1—O2	113.8 (6)
N6—C13—N7	130.4 (6)	O1—S1—C20	103.1 (5)
N5—C13—N7	118.5 (5)	O3—S1—C20	104.5 (5)
C15—C14—C19	121.1 (7)	O2—S1—C20	103.4 (5)
C15—C14—N8	115.2 (7)
C6—C1—C2—C3	−1.4 (11)	N2—C7—N4—C8	−179.3 (5)
N1—C1—C2—C3	179.9 (6)	N3—C7—N4—C10	−174.5 (5)
C1—C2—C3—C4	0.3 (12)	N2—C7—N4—C10	7.2 (8)
C2—C3—C4—C5	1.3 (12)	N5—C10—N4—C8	−91.0 (8)
C3—C4—C5—C6	−1.7 (12)	N5—C10—N4—C7	81.0 (7)
C2—C1—C6—C5	1.0 (10)	C12—C11—N5—C13	0.3 (7)
N1—C1—C6—C5	179.5 (6)	C12—C11—N5—C10	176.1 (6)
C4—C5—C6—C1	0.6 (11)	N6—C13—N5—C11	−0.8 (7)
N4—C8—C9—N3	−0.3 (8)	N7—C13—N5—C11	−179.1 (5)
N5—C11—C12—N6	0.2 (9)	N6—C13—N5—C10	−176.5 (5)
C19—C14—C15—C16	0.5 (12)	N7—C13—N5—C10	5.2 (9)
N8—C14—C15—C16	−178.8 (7)	N4—C10—N5—C11	−88.1 (7)
C14—C15—C16—C17	−1.2 (13)	N4—C10—N5—C13	86.8 (7)
C15—C16—C17—C18	1.1 (15)	N5—C13—N6—C12	0.9 (7)
C16—C17—C18—C19	−0.1 (16)	N7—C13—N6—C12	178.9 (6)
C15—C14—C19—C18	0.5 (12)	N5—C13—N6—Ag1ii	171.3 (4)
N8—C14—C19—C18	179.7 (8)	N7—C13—N6—Ag1ii	−10.6 (9)
C17—C18—C19—C14	−0.6 (14)	C11—C12—N6—C13	−0.7 (8)
C6—C1—N1—N2	3.2 (9)	C11—C12—N6—Ag1ii	−169.3 (5)
C2—C1—N1—N2	−178.2 (6)	N6—C13—N7—N8	−1.3 (9)
C1—N1—N2—C7	−177.8 (5)	N5—C13—N7—N8	176.7 (5)
N3—C7—N2—N1	2.4 (8)	C13—N7—N8—C14	−176.8 (5)
N4—C7—N2—N1	−179.7 (5)	C15—C14—N8—N7	170.3 (6)
N4—C7—N3—C9	0.8 (6)	C19—C14—N8—N7	−9.0 (9)
N2—C7—N3—C9	178.9 (6)	F2—C20—S1—O1	−177.9 (10)
N4—C7—N3—Ag1	174.6 (4)	F1—C20—S1—O1	54.1 (10)
N2—C7—N3—Ag1	−7.3 (8)	F3—C20—S1—O1	−61.1 (9)
C8—C9—N3—C7	−0.3 (7)	F2—C20—S1—O3	63.9 (10)
C8—C9—N3—Ag1	−172.8 (5)	F1—C20—S1—O3	−64.1 (10)
N6i—Ag1—N3—C7	−170.1 (5)	F3—C20—S1—O3	−179.4 (8)
N6i—Ag1—N3—C9	1.5 (9)	F2—C20—S1—O2	−55.5 (11)
C9—C8—N4—C7	0.8 (7)	F1—C20—S1—O2	176.5 (10)
C9—C8—N4—C10	174.1 (6)	F3—C20—S1—O2	61.3 (10)
N3—C7—N4—C8	−1.0 (7)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···O1iii	0.97	2.50	3.285 (10)	138.
C8—H8···O2iv	0.93	2.31	3.021 (10)	133.

Table 1

Selected bond lengths (Å)

Ag1—N3	2.152 (5)
Ag1—N6i	2.174 (6)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10B⋯O1i	0.97	2.50	3.285 (10)	138
C8—H8⋯O2ii	0.93	2.31	3.021 (10)	133

Symmetry codes: (i) ; (ii) .