4-[3-(Isonicotino-yloxy)propoxycarbon-yl]pyridinium diiodidoargentate(I).

The structure of the title compound, (C(15)H(15)N(2)O(4))[AgI(2)], consists of an organic 4-[3-(isonicotino-yloxy)propoxycarbon-yl]pyridinium cation which has a gauche-gauche (O/C/C/C-O/C/C/C or GG') conformation and lies on a twofold rotation axis, which passes through the central C atom of the aliphatic chain, and an inorganic [AgI(2)](-) anion. In the complex anion, the Ag(+) cation is bound to two I(-) anions in a linear geometry. The anion was modelled assuming disorder around a crystallographic inversion centre near the location of the Ag(+) cation. The crystal packing is stabilized by a strong inter-molecular N-H⋯N hydrogen bond, which links the cations into zigzag chains with graph-set notation C(16) running along the face diagonal of the ac plane. The N-bound H atom is disordered over two equally occupied symmetry-equivalent sites, so that the mol-ecule has a pyridinium ring at one end and a pyridine ring at the other.

Related literature

For a related structure, see: Brito et al. (2010 ▶). For conformation definitions, see: Carlucci et al. (2002 ▶). For coordination polymers, see: Brito et al. (2011 ▶); Albanez et al. (2011 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶). For polymeric organic-inorganic materials, see: Blake et al. (1999 ▶). For mol­ecular geometry calculations, see: Macrae et al. (2008 ▶).

Experimental

Crystal data

(C15H15N2O4)[n class="Chemical">AgI2]

M = 648.96

Monoclinic,

a = 14.8788 (7) Å

b = 5.4712 (3) Å

c = 24.5008 (11) Å

β = 95.347 (4)°

V = 1985.81 (17) Å3

Z = 4

Mo Kα radiation

μ = 4.14 mm−1

T = 173 K

0.22 × 0.13 × 0.10 mm

Data collection

Stoe IPDS II two-circle diffractometer

Absorption correction: multi-scan (MULABS; Spek, 2009 ▶; Blessing, 1995 ▶) T min = 0.463, T max = 0.682

9000 measured reflections

2158 independent reflections

1821 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.119

S = 1.03

2158 reflections

124 parameters

H-atom parameters constrained

Δρmax = 1.23 e Å−3

Δρmin = −0.76 e Å−3

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811047295/zl2424sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811047295/zl2424Isup2.hkl

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

(C15H15N2O4)[AgI2]	F(000) = 1216
Mr = 648.96	Dx = 2.171 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 9489 reflections
a = 14.8788 (7) Å	θ = 2.8–27.5°
b = 5.4712 (3) Å	µ = 4.14 mm−1
c = 24.5008 (11) Å	T = 173 K
β = 95.347 (4)°	Plate, red
V = 1985.81 (17) Å3	0.22 × 0.13 × 0.10 mm
Z = 4

Stoe IPDS II two-circle diffractometer	2158 independent reflections
Radiation source: fine-focus sealed tube	1821 reflections with I > 2σ(I)
graphite	Rint = 0.053
ω scans	θmax = 27.1°, θmin = 2.8°
Absorption correction: multi-scan (MULABS; Spek, 2009; Blessing, 1995)	h = −18→18
Tmin = 0.463, Tmax = 0.682	k = −6→6
9000 measured reflections	l = −27→31

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0748P)2 + 3.0902P] where P = (Fo2 + 2Fc2)/3
2158 reflections	(Δ/σ)max < 0.001
124 parameters	Δρmax = 1.23 e Å−3
0 restraints	Δρmin = −0.76 e Å−3

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	Occ. (<1)
Ag1	0.0035 (2)	0.5344 (4)	0.50664 (10)	0.0480 (4)	0.50
I1	0.0644 (2)	0.7876 (5)	0.60644 (12)	0.0697 (6)	0.50
I2	−0.0570 (2)	0.2745 (6)	0.40629 (12)	0.0707 (6)	0.50
O1	0.10823 (19)	0.3522 (6)	0.79400 (11)	0.0484 (6)
O2	0.1809 (2)	0.0578 (5)	0.75220 (11)	0.0488 (7)
C1	0.1569 (2)	0.1523 (7)	0.79293 (15)	0.0378 (7)
C2	0.0819 (3)	0.4755 (8)	0.74215 (17)	0.0467 (9)
H2A	0.0679	0.3539	0.7126	0.056*
H2B	0.1315	0.5813	0.7318	0.056*
C3	0.0000	0.6262 (11)	0.7500	0.0485 (12)
H3A	−0.0133	0.7329	0.7176	0.058*
C11	0.1794 (2)	0.0487 (7)	0.84926 (15)	0.0389 (7)
C12	0.2319 (3)	−0.1588 (8)	0.85514 (16)	0.0466 (8)
H12	0.2521	−0.2369	0.8239	0.056*
C13	0.2549 (4)	−0.2519 (8)	0.90675 (19)	0.0539 (10)
H13	0.2926	−0.3921	0.9110	0.065*
N14	0.2250 (3)	−0.1481 (8)	0.95113 (14)	0.0548 (9)
H14	0.2395	−0.2113	0.9838	0.066*	0.50
C15	0.1735 (3)	0.0493 (9)	0.94599 (18)	0.0554 (10)
H15	0.1531	0.1200	0.9780	0.066*
C16	0.1487 (3)	0.1559 (9)	0.89617 (17)	0.0496 (9)
H16	0.1118	0.2980	0.8935	0.060*

	U11	U22	U33	U12	U13	U23
Ag1	0.0385 (5)	0.0570 (12)	0.0501 (11)	0.0024 (7)	0.0122 (7)	0.0237 (7)
I1	0.0575 (7)	0.0881 (15)	0.0641 (12)	0.0079 (8)	0.0091 (7)	0.0217 (8)
I2	0.0617 (7)	0.0853 (14)	0.0660 (13)	−0.0011 (7)	0.0104 (8)	0.0195 (8)
O1	0.0526 (15)	0.0558 (16)	0.0368 (13)	0.0087 (13)	0.0033 (11)	−0.0008 (12)
O2	0.0654 (18)	0.0475 (15)	0.0346 (13)	0.0040 (13)	0.0098 (12)	0.0017 (12)
C1	0.0356 (16)	0.0426 (18)	0.0354 (17)	−0.0036 (14)	0.0042 (13)	−0.0003 (15)
C2	0.043 (2)	0.052 (2)	0.045 (2)	0.0030 (16)	0.0026 (16)	0.0053 (17)
C3	0.041 (3)	0.048 (3)	0.056 (3)	0.000	0.003 (2)	0.000
C11	0.0388 (17)	0.0441 (18)	0.0345 (17)	−0.0064 (14)	0.0069 (13)	−0.0018 (15)
C12	0.056 (2)	0.046 (2)	0.0383 (19)	−0.0009 (17)	0.0077 (16)	−0.0010 (16)
C13	0.071 (3)	0.047 (2)	0.043 (2)	0.0023 (18)	0.0070 (19)	0.0031 (17)
N14	0.067 (2)	0.061 (2)	0.0355 (17)	−0.0051 (19)	0.0039 (15)	0.0048 (16)
C15	0.060 (2)	0.072 (3)	0.0348 (19)	−0.003 (2)	0.0105 (17)	−0.006 (2)
C16	0.051 (2)	0.061 (2)	0.0378 (19)	0.0045 (19)	0.0076 (15)	−0.0029 (18)

Ag1—I1	2.882 (3)	C11—C12	1.378 (6)
Ag1—I2	2.909 (3)	C11—C16	1.404 (5)
O1—C1	1.313 (5)	C12—C13	1.376 (6)
O1—C2	1.459 (5)	C12—H12	0.9500
O2—C1	1.207 (5)	C13—N14	1.339 (6)
C1—C11	1.501 (5)	C13—H13	0.9500
C2—C3	1.498 (5)	N14—C15	1.322 (6)
C2—H2A	0.9900	N14—H14	0.8800
C2—H2B	0.9900	C15—C16	1.372 (6)
C3—C2i	1.498 (5)	C15—H15	0.9500
C3—H3A	0.9900	C16—H16	0.9500
I1—Ag1—I2	179.44 (19)	C16—C11—C1	122.2 (4)
C1—O1—C2	118.1 (3)	C13—C12—C11	119.4 (4)
O2—C1—O1	125.4 (3)	C13—C12—H12	120.3
O2—C1—C11	122.8 (3)	C11—C12—H12	120.3
O1—C1—C11	111.9 (3)	N14—C13—C12	121.1 (4)
O1—C2—C3	107.4 (3)	N14—C13—H13	119.5
O1—C2—H2A	110.2	C12—C13—H13	119.5
C3—C2—H2A	110.2	C15—N14—C13	120.2 (4)
O1—C2—H2B	110.2	C15—N14—H14	119.9
C3—C2—H2B	110.2	C13—N14—H14	119.9
H2A—C2—H2B	108.5	N14—C15—C16	122.5 (4)
C2—C3—C2i	113.2 (5)	N14—C15—H15	118.8
C2—C3—H3A	109.0	C16—C15—H15	118.8
C2i—C3—H3A	108.8	C15—C16—C11	118.0 (4)
C12—C11—C16	118.9 (4)	C15—C16—H16	121.0
C12—C11—C1	118.9 (3)	C11—C16—H16	121.0
C2—O1—C1—O2	−1.3 (6)	C16—C11—C12—C13	−1.7 (6)
C2—O1—C1—C11	179.4 (3)	C1—C11—C12—C13	178.3 (4)
C1—O1—C2—C3	157.3 (4)	C11—C12—C13—N14	1.9 (7)
O1—C2—C3—C2i	−68.0 (3)	C12—C13—N14—C15	−1.0 (7)
O2—C1—C11—C12	2.1 (6)	C13—N14—C15—C16	0.0 (7)
O1—C1—C11—C12	−178.6 (3)	N14—C15—C16—C11	0.2 (7)
O2—C1—C11—C16	−177.9 (4)	C12—C11—C16—C15	0.7 (6)
O1—C1—C11—C16	1.4 (5)	C1—C11—C16—C15	−179.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N14—H14···N14ii	0.88	1.80	2.684 (7)	176.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N14—H14⋯N14i	0.88	1.80	2.684 (7)	176

Symmetry code: (i) .