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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): m1535.
Published online 2009 November 7. doi:  10.1107/S1600536809045838
PMCID: PMC2972043

Bis(2-methyl-1H-imidazole-κN 3)silver(I) nitrate dihydrate

Abstract

The AgI atom in the salt, [Ag(C4H6N2)2]NO3·2H2O, shows a nearly linear coordination [N—Ag—N = 178.26 (7)°]. The cation, anion and water mol­ecules are linked by N—H(...)O and O—H(...)O hydrogen bonds into a layer motif extending parallel to (101).

Related literature

For the crystal structure of [Ag(C4H6N2)2][NO3]·CH3OH, see: Liu et al. (2006 [triangle]).

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Object name is e-65-m1535-scheme1.jpg

Experimental

Crystal data

  • [Ag(C4H6N2)2]NO3·2H2O
  • M r = 370.13
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-m1535-efi1.jpg
  • a = 6.8001 (4) Å
  • b = 17.0196 (9) Å
  • c = 12.1453 (7) Å
  • β = 101.691 (1)°
  • V = 1376.48 (13) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.49 mm−1
  • T = 295 K
  • 0.21 × 0.19 × 0.17 mm

Data collection

  • Bruker APEX2 diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.745, T max = 0.786
  • 7483 measured reflections
  • 2721 independent reflections
  • 2083 reflections with I > 2σ(I)
  • R int = 0.020

Refinement

  • R[F 2 > 2σ(F 2)] = 0.024
  • wR(F 2) = 0.073
  • S = 0.99
  • 2721 reflections
  • 198 parameters
  • 6 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.54 e Å−3
  • Δρmin = −0.34 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809045838/bt5122sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809045838/bt5122Isup2.hkl

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

Acknowledgments

We thank Tianjin Agricultural University and the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

Silver nitrate (0.5 mmol, 0.085 g) and 2-methyl-1H-imidazole (0.5 mmol, 0.041 g) in water (15 ml) were heated in a Parr bomb at 433 K for three days. Crystals of the adduct were isolated from the cool mixture in 30% yield.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H 0.93–0.97 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5U(C). The amino and water H atoms were located in a difference Fourier map, and were refined with a distance restraint of N–H = O–H = 0.85±0.01 Å; their displacement parameters were refined.

The final difference Fourier map had a peak that was displaced by 0.5 along y relative to Ag1. Thus, for the reflections with k odd a scale factor was refined to 1.035 (2) with respect to the reflections with k even. Although the refinement was not significantly improved, the final difference Fourier map now did not have any large peaks.

Figures

Fig. 1.
Anisotropic displacement ellipsoid plot (Barbour, 2001) of [Ag(C4H6N2)2][NO3].2H2O at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

[Ag(C4H6N2)2]NO3·2H2OF(000) = 744
Mr = 370.13Dx = 1.786 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3827 reflections
a = 6.8001 (4) Åθ = 2.9–26.1°
b = 17.0196 (9) ŵ = 1.49 mm1
c = 12.1453 (7) ÅT = 295 K
β = 101.691 (1)°Block, colorless
V = 1376.48 (13) Å30.21 × 0.19 × 0.17 mm
Z = 4

Data collection

Bruker APEX2 diffractometer2721 independent reflections
Radiation source: fine-focus sealed tube2083 reflections with I > 2σ(I)
graphiteRint = 0.020
[var phi] and ω scansθmax = 26.1°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −4→8
Tmin = 0.745, Tmax = 0.786k = −19→21
7483 measured reflectionsl = −15→14

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.024Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.073H atoms treated by a mixture of independent and constrained refinement
S = 0.99w = 1/[σ2(Fo2) + (0.0441P)2 + 0.0379P] where P = (Fo2 + 2Fc2)/3
2721 reflections(Δ/σ)max = 0.001
198 parametersΔρmax = 0.54 e Å3
6 restraintsΔρmin = −0.33 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Ag10.63346 (3)0.501978 (10)0.882866 (16)0.02240 (9)
O1−0.1909 (3)0.26078 (11)0.44924 (15)0.0315 (5)
O2−0.0592 (3)0.30353 (12)0.61645 (17)0.0404 (5)
O3−0.2399 (3)0.19831 (13)0.59642 (18)0.0458 (6)
O1w0.1172 (3)0.35094 (12)0.38606 (16)0.0266 (4)
O2w0.3941 (3)0.24560 (11)0.34310 (17)0.0292 (4)
N10.4754 (4)0.49985 (11)0.7163 (2)0.0217 (5)
N20.2877 (3)0.45702 (14)0.55959 (19)0.0257 (5)
H20.228 (4)0.4222 (13)0.514 (2)0.043 (9)*
N30.7904 (3)0.50045 (10)1.0498 (2)0.0201 (5)
N40.9606 (3)0.45734 (13)1.21030 (19)0.0219 (5)
H41.010 (4)0.4257 (12)1.2620 (16)0.025 (8)*
N5−0.1639 (3)0.25410 (13)0.55457 (19)0.0275 (5)
C10.3998 (4)0.56352 (16)0.6500 (2)0.0242 (6)
H10.42450.61600.66940.029*
C20.2853 (4)0.53782 (17)0.5535 (2)0.0267 (6)
H2A0.21770.56850.49440.032*
C30.4044 (4)0.43623 (15)0.6586 (2)0.0230 (6)
C40.4422 (4)0.35360 (15)0.6951 (3)0.0344 (7)
H4A0.55120.35170.75920.052*
H4B0.47640.32350.63490.052*
H4C0.32360.33210.71500.052*
C50.8772 (4)0.56384 (16)1.1123 (2)0.0232 (6)
H50.86520.61601.08930.028*
C60.9816 (4)0.53821 (16)1.2118 (2)0.0243 (6)
H61.05350.56871.26980.029*
C70.8427 (3)0.43705 (16)1.1119 (2)0.0206 (6)
C80.7814 (4)0.35502 (14)1.0811 (2)0.0318 (7)
H8A0.66740.35521.01980.048*
H8B0.74660.32901.14470.048*
H8C0.89060.32771.05890.048*
H110.192 (5)0.3164 (18)0.366 (3)0.089 (16)*
H120.029 (4)0.3258 (17)0.412 (3)0.052 (11)*
H210.517 (2)0.2499 (19)0.374 (3)0.060 (11)*
H220.392 (5)0.2426 (19)0.2737 (10)0.066 (12)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Ag10.01779 (13)0.02855 (14)0.01956 (14)−0.00075 (8)0.00074 (9)−0.00051 (8)
O10.0306 (10)0.0386 (11)0.0230 (11)−0.0041 (9)0.0001 (8)−0.0002 (8)
O20.0438 (12)0.0364 (12)0.0350 (13)−0.0013 (10)−0.0064 (10)−0.0126 (10)
O30.0549 (14)0.0491 (13)0.0362 (13)−0.0194 (11)0.0157 (11)−0.0026 (10)
O1w0.0270 (11)0.0253 (11)0.0268 (11)0.0008 (9)0.0038 (9)0.0015 (8)
O2w0.0280 (11)0.0296 (11)0.0276 (12)0.0012 (9)0.0001 (9)−0.0027 (9)
N10.0174 (11)0.0250 (12)0.0218 (12)−0.0016 (8)0.0017 (9)−0.0017 (9)
N20.0221 (12)0.0310 (14)0.0230 (13)0.0004 (10)0.0023 (10)−0.0050 (11)
N30.0196 (12)0.0203 (11)0.0203 (12)0.0006 (8)0.0036 (9)−0.0008 (8)
N40.0223 (12)0.0226 (12)0.0204 (12)0.0018 (10)0.0037 (10)0.0034 (10)
N50.0212 (11)0.0294 (12)0.0305 (14)0.0031 (10)0.0019 (10)−0.0050 (10)
C10.0249 (14)0.0219 (14)0.0254 (15)0.0006 (11)0.0038 (12)0.0017 (11)
C20.0258 (15)0.0308 (15)0.0239 (15)0.0043 (12)0.0060 (12)0.0043 (12)
C30.0171 (13)0.0274 (14)0.0251 (15)−0.0001 (11)0.0056 (11)−0.0034 (11)
C40.0351 (16)0.0227 (15)0.0426 (18)0.0058 (12)0.0008 (14)−0.0025 (12)
C50.0247 (15)0.0183 (13)0.0258 (16)−0.0015 (10)0.0033 (12)−0.0043 (11)
C60.0223 (14)0.0264 (15)0.0247 (15)−0.0048 (12)0.0058 (11)−0.0056 (12)
C70.0167 (13)0.0229 (14)0.0242 (15)0.0025 (10)0.0088 (11)0.0005 (11)
C80.0326 (15)0.0213 (14)0.0416 (18)−0.0033 (12)0.0075 (13)−0.0019 (12)

Geometric parameters (Å, °)

Ag1—N12.090 (2)N4—C61.384 (4)
Ag1—N32.091 (2)N4—H40.844 (10)
O1—N51.260 (3)C1—C21.342 (4)
O2—N51.250 (3)C1—H10.9300
O3—N51.238 (3)C2—H2A0.9300
O1w—H110.845 (10)C3—C41.481 (4)
O1w—H120.848 (10)C4—H4A0.9600
O2w—H210.844 (10)C4—H4B0.9600
O2w—H220.842 (10)C4—H4C0.9600
N1—C31.326 (3)C5—C61.344 (4)
N1—C11.385 (3)C5—H50.9300
N2—C31.347 (4)C6—H60.9300
N2—C21.377 (4)C7—C81.483 (3)
N2—H20.856 (10)C8—H8A0.9600
N3—C71.323 (3)C8—H8B0.9600
N3—C51.381 (3)C8—H8C0.9600
N4—C71.342 (3)
N1—Ag1—N3178.27 (7)N1—C3—N2110.0 (2)
H11—O1w—H12106 (4)N1—C3—C4126.5 (2)
H21—O2w—H22105 (3)N2—C3—C4123.5 (2)
C3—N1—C1106.2 (2)C3—C4—H4A109.5
C3—N1—Ag1125.87 (18)C3—C4—H4B109.5
C1—N1—Ag1127.32 (17)H4A—C4—H4B109.5
C3—N2—C2108.0 (2)C3—C4—H4C109.5
C3—N2—H2121 (2)H4A—C4—H4C109.5
C2—N2—H2131 (2)H4B—C4—H4C109.5
C7—N3—C5106.7 (2)C6—C5—N3109.3 (2)
C7—N3—Ag1126.03 (17)C6—C5—H5125.4
C5—N3—Ag1126.92 (16)N3—C5—H5125.4
C7—N4—C6108.0 (2)C5—C6—N4106.1 (2)
C7—N4—H4125.1 (18)C5—C6—H6127.0
C6—N4—H4126.9 (19)N4—C6—H6127.0
O3—N5—O2120.2 (2)N3—C7—N4109.9 (2)
O3—N5—O1119.9 (2)N3—C7—C8126.5 (2)
O2—N5—O1119.9 (2)N4—C7—C8123.6 (2)
C2—C1—N1109.5 (2)C7—C8—H8A109.5
C2—C1—H1125.3C7—C8—H8B109.5
N1—C1—H1125.3H8A—C8—H8B109.5
C1—C2—N2106.3 (2)C7—C8—H8C109.5
C1—C2—H2A126.9H8A—C8—H8C109.5
N2—C2—H2A126.9H8B—C8—H8C109.5
C3—N1—C1—C2−0.2 (3)C7—N3—C5—C60.1 (3)
Ag1—N1—C1—C2−171.9 (2)Ag1—N3—C5—C6−173.71 (19)
N1—C1—C2—N20.4 (3)N3—C5—C6—N40.5 (3)
C3—N2—C2—C1−0.5 (3)C7—N4—C6—C5−1.0 (3)
C1—N1—C3—N2−0.1 (3)C5—N3—C7—N4−0.8 (3)
Ag1—N1—C3—N2171.74 (19)Ag1—N3—C7—N4173.13 (18)
C1—N1—C3—C4−179.5 (3)C5—N3—C7—C8178.6 (2)
Ag1—N1—C3—C4−7.7 (4)Ag1—N3—C7—C8−7.5 (4)
C2—N2—C3—N10.4 (3)C6—N4—C7—N31.1 (3)
C2—N2—C3—C4179.8 (2)C6—N4—C7—C8−178.2 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2···O1w0.86 (1)1.99 (1)2.838 (3)169 (3)
N4—H4···O1wi0.84 (1)1.99 (1)2.837 (3)178 (3)
O1w—H11···O2w0.85 (1)1.89 (1)2.726 (3)170 (4)
O1w—H12···O10.85 (1)1.99 (1)2.826 (3)171 (3)
O2w—H21···O1ii0.84 (1)2.02 (1)2.867 (3)179 (4)
O2w—H22···O2iii0.84 (1)2.15 (2)2.955 (3)159 (3)

Symmetry codes: (i) x+1, y, z+1; (ii) x+1, y, z; (iii) x+1/2, −y+1/2, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5122).

References

  • Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.
  • Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
  • Liu, J., Su, X.-Y., Wang, W.-H., Mao, Z.-H. & Xie, R.-G. (2006). Acta Cryst. E62, m1173–m1174.
  • Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2009). publCIF. In preparation.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography