Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807052269/lx2023sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807052269/lx2023Isup2.hkl |
CCDC reference: 646844
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.013 Å
- R factor = 0.036
- wR factor = 0.096
- Data-to-parameter ratio = 24.8
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 1.06 PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 14
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 1.056 Tmax scaled 0.264 Tmin scaled 0.148 REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.48 From the CIF: _reflns_number_total 2749 Count of symmetry unique reflns 1516 Completeness (_total/calc) 181.33% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1233 Fraction of Friedel pairs measured 0.813 Are heavy atom types Z>Si present yes PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 5 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For the crystal structure of four-coordinated [Ag2I4] chain compounds, see: Thackeray & Coetzer (1975), Peters et al. (1984), Alcock et al. (2003), Li et al. (2004) and Niu et al. (2005).
For related literature, see: Caitlin et al. (2003); Huang & Xie (1988); MaArdle (1995); Sheldrick (2001).
The title compound was synthesized by self-assembling reaction of silver iodide and N-ethyl-4-methylpyridinium iodide (Huang & Xie, 1988). N-Ethyl-4-methylpyridinium iodide (0.25 g, 1.0 mmol) and silver iodide (0.23 g, 1 mmol) were dissolved in DMF (15 ml). After being stirred at room temperature for 20 min. Finally, a kind of yellow clear solution was formed and filtered. Then the solution was allowed to evaporate at room temperature for one week. The title compound was obtained as a kind of yellow crystals [yield 0.15 g (31% based on Ag)]. Anal. Calcd. for C8H12NAgI2 (483.86): C19.88, H 2.47, N 2.90%. Found: C,19.84, H 2.48, N 2.89%.
All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93 Å for aromatic H atoms, 0.97 Å for methylene H atoms and 0.96 Å for methyl H atoms, respectively, and with Uiso(H) = 1.2Ueq(C) for aromatic and methylene H atoms, Uiso(H) = 1.5Ueq(C) for methyl H atoms. In the absence of significant anomalous scattering effects, Friedel pairs were merged.
In the title compound, each silver atom coordinated by four iodine atoms forms [AgI4] tetrahedrons (Fig. 1). The [AgI4] tetrahedron is highly distorted with Ag—I distances and I—Ag—I angles compared to an ideal tetrahedron (Table 1). This trans edge-sharing [AgI4] tetrahedron results in two types of one-dimensional [(AgI2)-]n anion chains which are along the crystallographic c axis. The further stability comes from a weak C—H···I hydrogen bond (Horn et al., 2003) between a methylene H of the cation part and I atom of anion part to give a 3-D network (Table 2 & Fig. 2).
For the crystal structure of four-coordinated [Ag2I4] chain compounds, see: Thackeray & Coetzer (1975), Peters et al. (1984), Alcock et al. (2003), Li et al. (2004) and Niu et al. (2005).
For related literature, see: Caitlin et al. (2003); Huang & Xie (1988); MaArdle (1995); Sheldrick (2001).
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).
(C8H12N)[AgI2] | Dx = 2.631 Mg m−3 |
Mr = 483.86 | Mo Kα radiation, λ = 0.71073 Å |
Tetragonal, P42bc | Cell parameters from 25 reflections |
Hall symbol: P 4c -2ab | θ = 12–18° |
a = 18.205 (3) Å | µ = 6.66 mm−1 |
c = 7.371 (2) Å | T = 293 K |
V = 2442.9 (9) Å3 | Club, yellow |
Z = 8 | 0.30 × 0.22 × 0.20 mm |
F(000) = 1760 |
Rigaku Weissenberg IP diffractometer | 2749 independent reflections |
Radiation source: rotor target | 2267 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.053 |
Detector resolution: None pixels mm-1 | θmax = 27.5°, θmin = 3.2° |
scintillation counter scans | h = −23→23 |
Absorption correction: multi-scan (TEXRAY; Molecular Structure Corporation, 1999) | k = −23→23 |
Tmin = 0.140, Tmax = 0.250 | l = −9→9 |
21995 measured reflections |
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)] = 0.036 | H-atom parameters constrained |
wR(F2) = 0.096 | w = 1/[σ2(Fo2) + (0.0469P)2 + 1.1814P] where P = (Fo2 + 2Fc2)/3 |
S = 1.12 | (Δ/σ)max < 0.001 |
2749 reflections | Δρmax = 0.55 e Å−3 |
111 parameters | Δρmin = −0.75 e Å−3 |
1 restraint | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.06 (6) |
(C8H12N)[AgI2] | Z = 8 |
Mr = 483.86 | Mo Kα radiation |
Tetragonal, P42bc | µ = 6.66 mm−1 |
a = 18.205 (3) Å | T = 293 K |
c = 7.371 (2) Å | 0.30 × 0.22 × 0.20 mm |
V = 2442.9 (9) Å3 |
Rigaku Weissenberg IP diffractometer | 2749 independent reflections |
Absorption correction: multi-scan (TEXRAY; Molecular Structure Corporation, 1999) | 2267 reflections with I > 2σ(I) |
Tmin = 0.140, Tmax = 0.250 | Rint = 0.053 |
21995 measured reflections |
R[F2 > 2σ(F2)] = 0.036 | H-atom parameters constrained |
wR(F2) = 0.096 | Δρmax = 0.55 e Å−3 |
S = 1.12 | Δρmin = −0.75 e Å−3 |
2749 reflections | Absolute structure: Flack (1983) |
111 parameters | Absolute structure parameter: 0.06 (6) |
1 restraint |
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 | ||
I1 | 0.38094 (3) | 0.99613 (3) | 1.14714 (10) | 0.05327 (15) | |
I2 | 0.10725 (3) | 0.94396 (3) | 1.23364 (12) | 0.05458 (15) | |
Ag1 | 0.5000 | 1.0000 | 0.8979 (2) | 0.0671 (3) | |
Ag2 | 0.0000 | 1.0000 | 1.48388 (18) | 0.0665 (3) | |
N | 0.2267 (4) | 0.8906 (4) | 0.7893 (8) | 0.0460 (15) | |
C1 | 0.1605 (4) | 0.8590 (5) | 0.7740 (11) | 0.055 (2) | |
H1 | 0.1190 | 0.8872 | 0.7510 | 0.066* | |
C2 | 0.1552 (5) | 0.7847 (5) | 0.7928 (12) | 0.058 (2) | |
H2 | 0.1092 | 0.7627 | 0.7835 | 0.069* | |
C3 | 0.2152 (5) | 0.7414 (5) | 0.8250 (11) | 0.053 (2) | |
C4 | 0.2822 (5) | 0.7770 (5) | 0.8414 (12) | 0.054 (2) | |
H4 | 0.3243 | 0.7499 | 0.8655 | 0.064* | |
C5 | 0.2870 (4) | 0.8504 (5) | 0.8227 (11) | 0.0485 (18) | |
H5 | 0.3324 | 0.8735 | 0.8332 | 0.058* | |
C6 | 0.2094 (7) | 0.6606 (6) | 0.8389 (15) | 0.080 (3) | |
H6A | 0.1998 | 0.6471 | 0.9626 | 0.121* | |
H6B | 0.2547 | 0.6386 | 0.8001 | 0.121* | |
H6C | 0.1700 | 0.6436 | 0.7632 | 0.121* | |
C7 | 0.2338 (5) | 0.9718 (5) | 0.7626 (14) | 0.062 (2) | |
H7A | 0.1854 | 0.9936 | 0.7517 | 0.074* | |
H7B | 0.2581 | 0.9935 | 0.8666 | 0.074* | |
C8 | 0.2772 (7) | 0.9867 (5) | 0.5952 (15) | 0.078 (3) | |
H8A | 0.2826 | 1.0388 | 0.5796 | 0.117* | |
H8B | 0.2521 | 0.9664 | 0.4921 | 0.117* | |
H8C | 0.3248 | 0.9645 | 0.6060 | 0.117* |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.0493 (2) | 0.0602 (3) | 0.0503 (3) | 0.0061 (2) | −0.0008 (3) | −0.0007 (3) |
I2 | 0.0519 (3) | 0.0537 (3) | 0.0581 (3) | 0.0063 (2) | −0.0008 (3) | −0.0024 (3) |
Ag1 | 0.0722 (8) | 0.0698 (8) | 0.0593 (5) | −0.0005 (5) | 0.000 | 0.000 |
Ag2 | 0.0693 (7) | 0.0660 (7) | 0.0641 (6) | −0.0027 (8) | 0.000 | 0.000 |
N | 0.047 (3) | 0.047 (3) | 0.044 (4) | 0.006 (3) | 0.005 (3) | 0.000 (3) |
C1 | 0.042 (4) | 0.066 (5) | 0.058 (6) | 0.005 (4) | 0.009 (3) | −0.008 (4) |
C2 | 0.044 (4) | 0.066 (5) | 0.063 (5) | −0.014 (4) | 0.009 (4) | −0.008 (4) |
C3 | 0.075 (6) | 0.050 (4) | 0.035 (3) | −0.013 (4) | −0.001 (4) | −0.001 (3) |
C4 | 0.061 (5) | 0.044 (4) | 0.056 (5) | 0.008 (4) | −0.013 (4) | 0.001 (4) |
C5 | 0.042 (4) | 0.052 (4) | 0.052 (4) | 0.004 (3) | −0.007 (4) | −0.003 (4) |
C6 | 0.116 (9) | 0.056 (6) | 0.070 (6) | −0.010 (6) | −0.029 (7) | 0.008 (5) |
C7 | 0.081 (6) | 0.042 (4) | 0.063 (5) | 0.010 (4) | −0.002 (5) | −0.004 (4) |
C8 | 0.109 (9) | 0.049 (5) | 0.076 (7) | −0.011 (5) | −0.001 (6) | 0.009 (4) |
Ag1—I1 | 2.842 (1) | C4—C5 | 1.35 (1) |
Ag1—I1i | 2.849 (1) | C4—H4 | 0.9300 |
Ag2—I2 | 2.873 (1) | C5—H5 | 0.9300 |
Ag2—I2ii | 2.871 (1) | C6—H6A | 0.9600 |
N—C1 | 1.34 (1) | C6—H6B | 0.9600 |
N—C5 | 1.34 (1) | C6—H6C | 0.9600 |
N—C7 | 1.50 (1) | C7—C8 | 1.490 (15) |
C1—C2 | 1.36 (2) | C7—H7A | 0.9700 |
C1—H1 | 0.9300 | C7—H7B | 0.9700 |
C2—C3 | 1.37 (1) | C8—H8A | 0.9600 |
C2—H2 | 0.9300 | C8—H8B | 0.9600 |
C3—C4 | 1.39 (1) | C8—H8C | 0.9600 |
C3—C6 | 1.48 (1) | ||
I1iii—Ag1—I1i | 117.20 (2) | C3—C4—H4 | 119.6 |
I1iii—Ag1—I1 | 99.45 (6) | N—C5—C4 | 120.5 (8) |
I1—Ag1—I1i | 112.43 (2) | N—C5—H5 | 119.8 |
I1i—Ag1—I1iv | 99.13 (6) | C4—C5—H5 | 119.8 |
I2ii—Ag2—I2v | 100.23 (5) | C3—C6—H6A | 109.5 |
I2v—Ag2—I2 | 114.31 (1) | C3—C6—H6B | 109.5 |
I2vi—Ag2—I2 | 100.12 (5) | H6A—C6—H6B | 109.5 |
Ag1—I1—Ag1vii | 80.71 (2) | C3—C6—H6C | 109.5 |
Ag2viii—I2—Ag2 | 79.83 (2) | H6A—C6—H6C | 109.5 |
C1—N—C5 | 121.1 (7) | H6B—C6—H6C | 109.5 |
C1—N—C7 | 119.4 (7) | C8—C7—N | 109.5 (7) |
C5—N—C7 | 119.5 (7) | C8—C7—H7A | 109.8 |
N—C1—C2 | 118.8 (8) | N—C7—H7A | 109.8 |
N—C1—H1 | 120.6 | C8—C7—H7B | 109.8 |
C2—C1—H1 | 120.6 | N—C7—H7B | 109.8 |
C1—C2—C3 | 122.2 (8) | H7A—C7—H7B | 108.2 |
C1—C2—H2 | 118.9 | C7—C8—H8A | 109.5 |
C3—C2—H2 | 118.9 | C7—C8—H8B | 109.5 |
C2—C3—C4 | 116.6 (8) | H8A—C8—H8B | 109.5 |
C2—C3—C6 | 122.0 (9) | C7—C8—H8C | 109.5 |
C4—C3—C6 | 121.5 (9) | H8A—C8—H8C | 109.5 |
C5—C4—C3 | 120.8 (8) | H8B—C8—H8C | 109.5 |
C5—C4—H4 | 119.6 | ||
Ag1vii—I1—Ag1—I1iii | 0.0 | C7—N—C1—C2 | 177.9 (8) |
Ag1vii—I1—Ag1—I1i | 124.75 (3) | C1—C2—C3—C6 | −177.8 (9) |
Ag1vii—I1—Ag1—I1iv | −121.36 (4) | C6—C3—C4—C5 | 177.9 (9) |
Ag2viii—I2—Ag2—I2ii | −122.65 (3) | C7—N—C5—C4 | −177.9 (8) |
Ag2viii—I2—Ag2—I2v | 122.65 (3) | C1—N—C7—C8 | −113.0 (9) |
Ag2viii—I2—Ag2—I2vi | 0.0 | C5—N—C7—C8 | 65.0 (11) |
Symmetry codes: (i) y−1/2, x+1/2, z−1/2; (ii) −y+1, x+1, z+1/2; (iii) −x+1, −y+2, z; (iv) −y+3/2, −x+3/2, z−1/2; (v) y−1, −x+1, z+1/2; (vi) −x, −y+2, z; (vii) −y+3/2, −x+3/2, z+1/2; (viii) y−1, −x+1, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | (C8H12N)[AgI2] |
Mr | 483.86 |
Crystal system, space group | Tetragonal, P42bc |
Temperature (K) | 293 |
a, c (Å) | 18.205 (3), 7.371 (2) |
V (Å3) | 2442.9 (9) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 6.66 |
Crystal size (mm) | 0.30 × 0.22 × 0.20 |
Data collection | |
Diffractometer | Rigaku Weissenberg IP |
Absorption correction | Multi-scan (TEXRAY; Molecular Structure Corporation, 1999) |
Tmin, Tmax | 0.140, 0.250 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 21995, 2749, 2267 |
Rint | 0.053 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.036, 0.096, 1.12 |
No. of reflections | 2749 |
No. of parameters | 111 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.55, −0.75 |
Absolute structure | Flack (1983) |
Absolute structure parameter | 0.06 (6) |
Computer programs: TEXRAY (Molecular Structure Corporation, 1999), TEXSAN (Molecular Structure Corporation, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEX (McArdle, 1995).
Ag1—I1 | 2.842 (1) | Ag2—I2 | 2.873 (1) |
Ag1—I1i | 2.849 (1) | Ag2—I2ii | 2.871 (1) |
I1iii—Ag1—I1i | 117.20 (2) | I2ii—Ag2—I2v | 100.23 (5) |
I1iii—Ag1—I1 | 99.45 (6) | I2v—Ag2—I2 | 114.31 (1) |
I1—Ag1—I1i | 112.43 (2) | I2vi—Ag2—I2 | 100.12 (5) |
I1i—Ag1—I1iv | 99.13 (6) |
Symmetry codes: (i) y−1/2, x+1/2, z−1/2; (ii) −y+1, x+1, z+1/2; (iii) −x+1, −y+2, z; (iv) −y+3/2, −x+3/2, z−1/2; (v) y−1, −x+1, z+1/2; (vi) −x, −y+2, z. |
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In the title compound, each silver atom coordinated by four iodine atoms forms [AgI4] tetrahedrons (Fig. 1). The [AgI4] tetrahedron is highly distorted with Ag—I distances and I—Ag—I angles compared to an ideal tetrahedron (Table 1). This trans edge-sharing [AgI4] tetrahedron results in two types of one-dimensional [(AgI2)-]n anion chains which are along the crystallographic c axis. The further stability comes from a weak C—H···I hydrogen bond (Horn et al., 2003) between a methylene H of the cation part and I atom of anion part to give a 3-D network (Table 2 & Fig. 2).