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Acta Cryst. (2009). E65, m1535    [ doi:10.1107/S1600536809045838 ]

Bis(2-methyl-1H-imidazole-[kappa]N3)silver(I) nitrate dihydrate

F.-D. Cong, F.-Y. Yu, Z. Wei and S. W. Ng

Abstract top

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 top

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

Experimental top

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 top

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.

Computing details top

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

Figures top
[Figure 1] 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.
Bis(2-methyl-1H-imidazole-κN3)silver(I) nitrate dihydrate top
Crystal data top
[Ag(C4H6N2)2]NO3·2H2OF(000) = 744
Mr = 370.13Dx = 1.786 Mg m−3
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 mm−1
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 top
Bruker APEX2
diffractometer		2721 independent reflections
Radiation source: fine-focus sealed tube2083 reflections with I > 2σ(I)
graphiteRint = 0.020
φ 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 top
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 = 0.99 w = 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 Å−3
6 restraintsΔρmin = −0.33 e Å−3
Crystal data top
[Ag(C4H6N2)2]NO3·2H2OV = 1376.48 (13) Å3
Mr = 370.13Z = 4
Monoclinic, P21/nMo Kα radiation
a = 6.8001 (4) ŵ = 1.49 mm−1
b = 17.0196 (9) ÅT = 295 K
c = 12.1453 (7) Å0.21 × 0.19 × 0.17 mm
β = 101.691 (1)°
Data collection top
Bruker APEX2
diffractometer		2083 reflections with I > 2σ(I)
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		Rint = 0.020
Tmin = 0.745, Tmax = 0.786θmax = 26.1°
7483 measured reflectionsStandard reflections: 0
2721 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.024H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.073Δρmax = 0.54 e Å−3
S = 0.99Δρmin = −0.33 e Å−3
2721 reflectionsAbsolute structure: ?
198 parametersFlack parameter: ?
6 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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) top
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, °) top
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, °) top
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.
Table 1
Hydrogen-bond geometry (Å, °) top
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.
Acknowledgements top

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

references
References top

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.

Westrip, S. P. (2009). publCIF. In preparation.