supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportsimilar papers buy article online

sj2367 scheme

Acta Cryst. (2007). E63, m2970    [ doi:10.1107/S1600536807048441 ]

(E)-4-[4-(Dimethylamino)styryl]-1-isopropylpyridinium diiodidoargentate(I)

Y.-F. Liu, M. Lin, C.-C. Huang and J.-Z. Chen

Abstract top

The title compound, (C18H23N2)[AgI2], contains linear anions. In the crystal structure, weak nonclassical C-H...I hydrogen bonds link adjacent cations and anions.

Comment top

The synthesis of organic–inorganic complex materials has been extensively reported in recent years and shown to provide an efficacious method for the design of new materials. Owing to their potential applications as new functional solid materials, many complexes such as [(C22H50N2)(Ag2I4)]n (Li et al., 2004), (C8H20N)(Ag2I3)n (Ke et al., 2005) and (C6H14NO2)(Ag5Br8) (Kildea & White, 1984) have been prepared. In the search for a new organic–inorganic materials, we present here the synthesis and the structure of the title compound (I), Fig 1.

The structure consists of an organic 4-(4-(dimethylamino)stryl-1-isopropylpyridinium cation and an inorganic (AgI2)− anion. In the anion, each silver atom is bound to two iodine atoms in a nearly linear geometry with I1—Ag1—I2 177.41 (3)°. The two Ag—I bond lengths are 2.9200 (10) Å and 2.8847 (11) Å, with an average of 2.9024 Å. These are slightly longer than the average of 2.8784 Å reported for C8H20N)(Ag2I3) (Ke et al., 2005).

In the crystal structure, Fig. 2, weak non-classical C11—H11···I1i hydrogen bonds (i = −1/2 + x, 1/2 − y, 1/2 + z) link adjacent cations and anions.

Related literature top

For related structures, see: Ke et al. (2005); Kildea & White (1984); Li et al. (2004).

Experimental top

4-(4-(dimethylamino)stryl-1-isopropylpyridinium iodide (0.195 g, 0.5 mmol) and AgI (0.117 g, 0.5 mmol) were dissolved in 8 ml DMF. The solution was stirred until clear, and the pH adjusted to 5.5 by the addition of 10% HI/DMF. The solution was filtered and kept at room temperature for five days to obtain brown block-like crystals.

Refinement top

The H atoms were placed in idealized positions and treated as riding with d(C—H) = 0.93 Å, Uiso= 1.2Ueq(C) for aromatic 0.96 Å, Uiso = 1.5Ueq(C) for CH3 atoms and 0.98 Å, Uiso = 1.2Ueq(C) for the CH atoms.

Computing details top

Data collection: TEXRAY (Molecular Structure Corporation, 1999); cell refinement: TEXRAY (Molecular Structure Corporation, 1999); data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX (McArdle, 1995); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms.
[Figure 2] Fig. 2. Crystal packing for (I) with C—H···I hydrogen bonds drawn as dotted lines.
(E)-4-[4-(Dimethylamino)styryl]-1-isopropylpyridinium diiodidoargentate(I) top
Crystal data top
(C18H23N2)[AgI2]F000 = 1192
Mr = 629.05Dx = 1.936 Mg m−3
Monoclinic, P21/nMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 12724 reflections
a = 8.9356 (18) Åθ = 3.1–27.5º
b = 14.226 (3) ŵ = 3.80 mm−1
c = 16.988 (3) ÅT = 293 (2) K
β = 92.34 (3)ºBlock, brown
V = 2157.7 (7) Å30.10 × 0.10 × 0.10 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID imaging-plate
diffractometer		4947 independent reflections
Radiation source: fine-focus sealed tube2862 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.054
T = 293(2) Kθmax = 27.5º
ω scansθmin = 3.1º
Absorption correction: ψ scan
(TEXRAY; Molecular Structure Corporation, 1999)		h = −10→11
Tmin = 0.684, Tmax = 0.691k = −16→18
20713 measured reflectionsl = −22→22
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.053H-atom parameters constrained
wR(F2) = 0.184  w = 1/[σ2(Fo2) + (0.0839P)2 + 1.7625P]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max < 0.001
4947 reflectionsΔρmax = 1.24 e Å−3
212 parametersΔρmin = −1.09 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
(C18H23N2)[AgI2]V = 2157.7 (7) Å3
Mr = 629.05Z = 4
Monoclinic, P21/nMo Kα
a = 8.9356 (18) ŵ = 3.80 mm−1
b = 14.226 (3) ÅT = 293 (2) K
c = 16.988 (3) Å0.10 × 0.10 × 0.10 mm
β = 92.34 (3)º
Data collection top
Rigaku R-AXIS RAPID imaging-plate
diffractometer		4947 independent reflections
Absorption correction: ψ scan
(TEXRAY; Molecular Structure Corporation, 1999)		2862 reflections with I > 2σ(I)
Tmin = 0.684, Tmax = 0.691Rint = 0.054
20713 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.053212 parameters
wR(F2) = 0.184H-atom parameters constrained
S = 1.10Δρmax = 1.24 e Å−3
4947 reflectionsΔρmin = −1.09 e Å−3
Special details top

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 > 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
Ag10.43451 (6)0.37865 (5)0.21087 (3)0.0675 (2)
I10.61642 (8)0.21820 (5)0.16627 (4)0.0970 (3)
I20.27107 (8)0.54058 (5)0.26277 (4)0.1020 (3)
N1−0.6719 (8)0.9749 (5)0.5741 (4)0.081 (2)
N2−0.1385 (6)0.3379 (4)0.4027 (4)0.0611 (14)
C1−0.6132 (8)0.8939 (5)0.5480 (4)0.0623 (17)
C2−0.5300 (8)0.8344 (5)0.5997 (4)0.0651 (18)
H2−0.51430.85120.65230.078*
C3−0.4716 (8)0.7510 (5)0.5724 (4)0.0611 (17)
H3−0.41900.71210.60780.073*
C4−0.4885 (8)0.7230 (5)0.4946 (4)0.0589 (16)
C5−0.5726 (9)0.7822 (5)0.4451 (4)0.0674 (19)
H5−0.58870.76450.39270.081*
C6−0.6321 (10)0.8642 (5)0.4692 (5)0.074 (2)
H6−0.68630.90140.43320.089*
C7−0.4232 (8)0.6400 (5)0.4648 (5)0.0655 (18)
H7−0.44350.62830.41160.079*
C8−0.3366 (8)0.5761 (5)0.5025 (4)0.0606 (17)
H8−0.31660.58510.55610.073*
C9−0.2726 (8)0.4955 (5)0.4674 (4)0.0608 (17)
C10−0.1702 (9)0.4393 (5)0.5101 (4)0.070 (2)
H10−0.14540.45460.56220.084*
C11−0.1058 (9)0.3628 (6)0.4774 (5)0.074 (2)
H11−0.03780.32710.50760.089*
C12−0.2360 (9)0.3897 (5)0.3599 (5)0.071 (2)
H12−0.25710.37370.30760.085*
C13−0.3063 (9)0.4666 (5)0.3917 (5)0.072 (2)
H13−0.37770.49930.36120.087*
C14−0.0663 (9)0.2531 (6)0.3643 (5)0.073 (2)
H14A−0.14480.21900.33410.088*
C150.0047 (12)0.1887 (7)0.4188 (6)0.097 (3)
H15A0.09590.21590.44020.146*
H15B0.02710.13130.39200.146*
H15C−0.06120.17570.46070.146*
C160.0414 (12)0.2936 (7)0.3065 (6)0.103 (3)
H16A0.12940.31630.33470.155*
H16B−0.00610.34460.27810.155*
H16C0.06900.24560.27010.155*
C17−0.6485 (13)1.0061 (7)0.6547 (6)0.106 (3)
H17A−0.69690.96340.68930.159*
H17B−0.69001.06790.66030.159*
H17C−0.54311.00780.66810.159*
C18−0.7621 (11)1.0351 (6)0.5204 (6)0.089 (3)
H18A−0.70391.05260.47650.134*
H18B−0.79171.09060.54790.134*
H18C−0.84971.00140.50180.134*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ag10.0614 (3)0.0983 (5)0.0419 (3)−0.0166 (3)−0.0102 (2)0.0125 (3)
I10.1135 (5)0.1104 (5)0.0666 (4)−0.0017 (4)−0.0036 (3)−0.0106 (3)
I20.1068 (5)0.1060 (5)0.0929 (5)0.0012 (4)0.0002 (4)0.0203 (4)
N10.102 (5)0.067 (4)0.070 (4)0.026 (4)−0.018 (4)−0.005 (3)
N20.065 (3)0.060 (3)0.058 (4)0.004 (3)−0.004 (3)0.002 (3)
C10.060 (4)0.071 (4)0.055 (4)0.011 (4)−0.003 (3)−0.006 (3)
C20.071 (4)0.075 (5)0.048 (4)0.009 (4)−0.007 (3)0.001 (3)
C30.065 (4)0.068 (4)0.050 (4)0.013 (4)0.002 (3)0.010 (3)
C40.065 (4)0.055 (4)0.056 (4)0.006 (3)−0.002 (3)0.000 (3)
C50.080 (5)0.071 (5)0.050 (4)0.010 (4)−0.007 (4)−0.009 (3)
C60.090 (5)0.068 (5)0.063 (5)0.022 (4)−0.018 (4)0.000 (4)
C70.072 (4)0.068 (4)0.056 (4)−0.005 (4)−0.002 (3)−0.002 (4)
C80.072 (4)0.062 (4)0.049 (4)−0.002 (4)0.004 (3)−0.001 (3)
C90.068 (4)0.061 (4)0.053 (4)−0.006 (3)0.001 (3)0.007 (3)
C100.087 (5)0.072 (5)0.050 (4)0.010 (4)−0.009 (4)−0.003 (3)
C110.086 (5)0.080 (5)0.055 (5)0.012 (4)−0.013 (4)0.009 (4)
C120.079 (5)0.072 (5)0.060 (5)0.013 (4)−0.018 (4)−0.001 (4)
C130.079 (5)0.064 (5)0.072 (5)0.015 (4)−0.015 (4)−0.012 (4)
C140.079 (5)0.076 (5)0.064 (5)0.019 (4)0.009 (4)−0.003 (4)
C150.115 (7)0.078 (6)0.101 (7)0.036 (5)0.027 (6)0.018 (5)
C160.117 (8)0.105 (7)0.092 (7)0.025 (6)0.041 (6)0.014 (6)
C170.135 (8)0.091 (6)0.090 (7)0.031 (6)−0.010 (6)−0.028 (5)
C180.104 (6)0.068 (5)0.095 (7)0.027 (5)−0.003 (5)0.009 (5)
Geometric parameters (Å, °) top
Ag1—I22.8847 (11)C9—C131.372 (10)
Ag1—I12.9200 (10)C9—C101.396 (10)
N1—C11.349 (9)C10—C111.360 (11)
N1—C171.447 (11)C10—H100.9300
N1—C181.468 (10)C11—H110.9300
N2—C121.333 (9)C12—C131.382 (11)
N2—C111.339 (9)C12—H120.9300
N2—C141.526 (10)C13—H130.9300
C1—C61.407 (10)C14—C151.433 (11)
C1—C21.410 (10)C14—C161.516 (12)
C2—C31.384 (10)C14—H14A0.9800
C2—H20.9300C15—H15A0.9600
C3—C41.382 (10)C15—H15B0.9600
C3—H30.9300C15—H15C0.9600
C4—C51.388 (10)C16—H16A0.9600
C4—C71.420 (10)C16—H16B0.9600
C5—C61.352 (10)C16—H16C0.9600
C5—H50.9300C17—H17A0.9600
C6—H60.9300C17—H17B0.9600
C7—C81.339 (10)C17—H17C0.9600
C7—H70.9300C18—H18A0.9600
C8—C91.423 (11)C18—H18B0.9600
C8—H80.9300C18—H18C0.9600
I2—Ag1—I1176.04 (3)N2—C11—H11119.4
C1—N1—C17122.1 (7)C10—C11—H11119.4
C1—N1—C18120.3 (7)N2—C12—C13121.5 (7)
C17—N1—C18117.6 (7)N2—C12—H12119.2
C12—N2—C11118.9 (7)C13—C12—H12119.2
C12—N2—C14118.8 (6)C9—C13—C12121.1 (7)
C11—N2—C14122.3 (6)C9—C13—H13119.4
N1—C1—C6122.5 (7)C12—C13—H13119.4
N1—C1—C2120.7 (7)C15—C14—C16112.7 (7)
C6—C1—C2116.9 (7)C15—C14—N2114.4 (7)
C3—C2—C1120.2 (7)C16—C14—N2105.5 (7)
C3—C2—H2119.9C15—C14—H14A108.0
C1—C2—H2119.9C16—C14—H14A108.0
C4—C3—C2122.6 (6)N2—C14—H14A108.0
C4—C3—H3118.7C14—C15—H15A109.5
C2—C3—H3118.7C14—C15—H15B109.5
C3—C4—C5116.1 (7)H15A—C15—H15B109.5
C3—C4—C7123.3 (7)C14—C15—H15C109.5
C5—C4—C7120.6 (7)H15A—C15—H15C109.5
C6—C5—C4123.3 (7)H15B—C15—H15C109.5
C6—C5—H5118.3C14—C16—H16A109.5
C4—C5—H5118.3C14—C16—H16B109.5
C5—C6—C1120.9 (7)H16A—C16—H16B109.5
C5—C6—H6119.5C14—C16—H16C109.5
C1—C6—H6119.5H16A—C16—H16C109.5
C8—C7—C4129.2 (7)H16B—C16—H16C109.5
C8—C7—H7115.4N1—C17—H17A109.5
C4—C7—H7115.4N1—C17—H17B109.5
C7—C8—C9125.5 (7)H17A—C17—H17B109.5
C7—C8—H8117.2N1—C17—H17C109.5
C9—C8—H8117.2H17A—C17—H17C109.5
C13—C9—C10115.5 (7)H17B—C17—H17C109.5
C13—C9—C8123.9 (7)N1—C18—H18A109.5
C10—C9—C8120.6 (7)N1—C18—H18B109.5
C11—C10—C9121.7 (7)H18A—C18—H18B109.5
C11—C10—H10119.2N1—C18—H18C109.5
C9—C10—H10119.2H18A—C18—H18C109.5
N2—C11—C10121.3 (7)H18B—C18—H18C109.5
C17—N1—C1—C6−178.3 (9)C7—C8—C9—C13−8.2 (12)
C18—N1—C1—C61.3 (13)C7—C8—C9—C10172.6 (7)
C17—N1—C1—C22.2 (13)C13—C9—C10—C111.8 (12)
C18—N1—C1—C2−178.2 (8)C8—C9—C10—C11−179.0 (7)
N1—C1—C2—C3179.3 (7)C12—N2—C11—C100.1 (12)
C6—C1—C2—C3−0.2 (12)C14—N2—C11—C10179.2 (7)
C1—C2—C3—C41.4 (12)C9—C10—C11—N2−0.2 (13)
C2—C3—C4—C5−2.2 (11)C11—N2—C12—C13−1.7 (12)
C2—C3—C4—C7176.8 (7)C14—N2—C12—C13179.2 (7)
C3—C4—C5—C61.9 (12)C10—C9—C13—C12−3.3 (12)
C7—C4—C5—C6−177.1 (8)C8—C9—C13—C12177.5 (8)
C4—C5—C6—C1−0.9 (14)N2—C12—C13—C93.4 (13)
N1—C1—C6—C5−179.6 (8)C12—N2—C14—C15−164.5 (8)
C2—C1—C6—C50.0 (12)C11—N2—C14—C1516.4 (11)
C3—C4—C7—C8−0.7 (13)C12—N2—C14—C1671.1 (10)
C5—C4—C7—C8178.3 (8)C11—N2—C14—C16−108.0 (9)
C4—C7—C8—C9−178.4 (7)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C11—H11···I1i0.933.053.879 (5)150
Symmetry codes: (i) x−1/2, −y+1/2, z+1/2.
Selected geometric parameters (Å, °) top
Ag1—I22.8847 (11)Ag1—I12.9200 (10)
I2—Ag1—I1176.04 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C11—H11···I1i0.933.053.879 (5)150
Symmetry codes: (i) x−1/2, −y+1/2, z+1/2.
Acknowledgements top

The authors are grateful for financial support from the National Natural Science Foundation of China (grant No. 0041814161).

references
References top

Ke, Z.-H., Cheng, Z.-R., Li, H.-H., Huang, C.-C., Xiao, G.-C. & Zhao, B. (2005). Chin. J. Struct. Chem. 24, 509–512.

Kildea, J.-D. & White, A.-H. (1984). Inorg. Chem. 23, 3825–3827.

Li, H.-H., Cheng, Z.-R., Huang, C.-C., Xiao, G.-C. & Ren, Y.-G. (2004). Chin. J. Struct. Chem. 23, 1009–1012.

McArdle, P. (1995). J. Appl. Cryst. 28, 65–?.

Molecular Structure Corporation (1999). TEXRAY (Version 1.10) and TEXSAN (Version 1.10). MSC, The Woodlands, Texas, USA.

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.