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In the title compound, [Ag(C3H4N2)2)]NO3, the AgI atom exhibits an approximately linear coordination geometry formed by two N atoms of imidazolium cations. The uncoordinated nitrate anion is linked to the AgI complex via N—H...O hydrogen bonding, generating a one-dimensional supra­molecular chain.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807036215/xu2302sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807036215/xu2302Isup2.hkl
Contains datablock I

CCDC reference: 657634

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.023
  • wR factor = 0.054
  • Data-to-parameter ratio = 16.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N5
Alert level G 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 27.60 From the CIF: _reflns_number_total 2266 Count of symmetry unique reflns 1371 Completeness (_total/calc) 165.28% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 895 Fraction of Friedel pairs measured 0.653 Are heavy atom types Z>Si present yes PLAT794_ALERT_5_G Check Predicted Bond Valency for Ag1 (9) 0.98
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Comment top

As part of the structural studies of AgI compounds involving the N-heterocycle ligand (Cai et al., 2003; Xu et al., 2002), we report here the synthesis and structure of the title compound.

The crystal of the compound consists of [Ag(C3N2H4)2)]+ cations and (NO3)- anions. Fig. 1 shows the structure of the cation. The AgI atom exhibits a AgN2 linear coordination geometry arising from two N atoms of imidazole molecules (Table 1). The uncoordinated nitrate anion interacts with imidazole by hydrogen bonding (Table 2), generating a one-dimensional supramolecular chain (Fig. 2).

Related literature top

For general background, see: Cai et al. (2003). For related literature, see: Xu et al. (2002).

Experimental top

A solution of AgNO3 (17 mg, 0.10 mmol) in CH3OH (10 ml) was slowly added to a solution of imidazole (14 mg, 0.20 mmol) in CH3OH (10 ml). The resultant solution was stirred for 10 min at room temperature and then filtered. After addition of diethyl ether (10 ml), the filtrate was cooled to 253 K. Microcrystalline material was collected after 24 h and dried under vacuum (yield: 20.8 mg, 68%). Colorless crystals suitable for X-ray diffraction were obtained in 2 d by slow diffusion of diethyl ether into a dilute solution of the title complex in methanol. The elemental analysis: calculated for C6H8N5AgO3 C 23.53, H 2.61, N 22.88%; found: C 23.48, H 2.68, N 22.75%.

Refinement top

H atoms were placed in idealized positions with C—H = 0.93 and N—H = 0.86 Å, and refined in riding mode with Uiso(H) = 1.2Ueq(C,N).

Structure description top

As part of the structural studies of AgI compounds involving the N-heterocycle ligand (Cai et al., 2003; Xu et al., 2002), we report here the synthesis and structure of the title compound.

The crystal of the compound consists of [Ag(C3N2H4)2)]+ cations and (NO3)- anions. Fig. 1 shows the structure of the cation. The AgI atom exhibits a AgN2 linear coordination geometry arising from two N atoms of imidazole molecules (Table 1). The uncoordinated nitrate anion interacts with imidazole by hydrogen bonding (Table 2), generating a one-dimensional supramolecular chain (Fig. 2).

For general background, see: Cai et al. (2003). For related literature, see: Xu et al. (2002).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The structure of the cation of the title compound. The atom-numbering scheme is shown at the 50% probability level.
[Figure 2] Fig. 2. One-dimensional chain constructed by N—H···O hydrogen bonds.
Bis(1H-imidazolium-κN3)silver(I) nitrate top
Crystal data top
[Ag(C3H4N2)2)]NO3F(000) = 600
Mr = 306.04Dx = 2.062 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 4145 reflections
a = 4.9941 (4) Åθ = 2.9–27.6°
b = 10.9250 (8) ŵ = 2.04 mm1
c = 18.0729 (12) ÅT = 298 K
V = 986.07 (13) Å3Block, colourless
Z = 40.22 × 0.20 × 0.16 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
2266 independent reflections
Radiation source: fine-focus sealed tube2175 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
φ and ω scansθmax = 27.6°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2002)
h = 64
Tmin = 0.630, Tmax = 0.720k = 149
5440 measured reflectionsl = 2223
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.023 w = 1/[σ2(Fo2) + (0.019P)2 + 0.36P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.054(Δ/σ)max = 0.001
S = 1.06Δρmax = 0.34 e Å3
2266 reflectionsΔρmin = 0.24 e Å3
137 parametersExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.0093 (6)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), with 896 Friedel pairs
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.01 (4)
Crystal data top
[Ag(C3H4N2)2)]NO3V = 986.07 (13) Å3
Mr = 306.04Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 4.9941 (4) ŵ = 2.04 mm1
b = 10.9250 (8) ÅT = 298 K
c = 18.0729 (12) Å0.22 × 0.20 × 0.16 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
2266 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2002)
2175 reflections with I > 2σ(I)
Tmin = 0.630, Tmax = 0.720Rint = 0.034
5440 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.023H-atom parameters constrained
wR(F2) = 0.054Δρmax = 0.34 e Å3
S = 1.06Δρmin = 0.24 e Å3
2266 reflectionsAbsolute structure: Flack (1983), with 896 Friedel pairs
137 parametersAbsolute structure parameter: 0.01 (4)
0 restraints
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 > 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ag10.05263 (5)0.56829 (2)0.394887 (14)0.04765 (9)
O11.0937 (6)0.0388 (3)0.25932 (16)0.0760 (9)
O21.1043 (5)0.0848 (2)0.35189 (14)0.0635 (7)
O30.8259 (7)0.1125 (3)0.26385 (16)0.0848 (10)
N10.2176 (4)0.7170 (2)0.39330 (15)0.0402 (5)
N20.5210 (5)0.8442 (2)0.35437 (16)0.0509 (7)
H20.64960.87410.32840.061*
N30.3587 (5)0.4350 (2)0.40299 (14)0.0432 (5)
N40.6233 (6)0.2898 (3)0.36536 (18)0.0565 (7)
H40.69160.23420.33750.068*
N51.0102 (5)0.0531 (2)0.29229 (14)0.0464 (6)
C10.4085 (7)0.7350 (3)0.34523 (19)0.0484 (8)
H10.45930.67880.30920.058*
C20.3967 (7)0.8998 (3)0.4119 (2)0.0526 (8)
H2A0.43310.97720.43080.063*
C30.2096 (7)0.8205 (3)0.43611 (19)0.0473 (7)
H30.09370.83380.47560.057*
C40.4128 (8)0.3589 (3)0.3494 (2)0.0549 (9)
H4A0.31600.35370.30550.066*
C50.7112 (7)0.3224 (3)0.4332 (2)0.0532 (9)
H50.85710.28980.45840.064*
C60.5441 (7)0.4125 (3)0.45737 (18)0.0479 (7)
H60.55400.45190.50290.058*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ag10.04804 (13)0.03896 (13)0.05596 (14)0.01227 (10)0.00079 (11)0.00013 (11)
O10.0810 (18)0.0742 (18)0.0727 (17)0.0439 (16)0.0231 (15)0.0295 (14)
O20.0756 (18)0.0613 (15)0.0537 (14)0.0062 (14)0.0167 (12)0.0076 (13)
O30.097 (2)0.093 (2)0.0643 (17)0.0642 (18)0.0247 (16)0.0118 (15)
N10.0386 (11)0.0367 (12)0.0453 (13)0.0026 (9)0.0026 (12)0.0025 (12)
N20.0406 (15)0.0531 (15)0.0592 (16)0.0129 (12)0.0048 (13)0.0106 (13)
N30.0435 (11)0.0367 (12)0.0494 (13)0.0065 (10)0.0037 (11)0.0005 (14)
N40.0585 (18)0.0440 (15)0.0671 (18)0.0162 (13)0.0129 (15)0.0032 (15)
N50.0491 (15)0.0461 (14)0.0441 (13)0.0118 (12)0.0015 (11)0.0010 (12)
C10.0458 (19)0.0465 (17)0.0529 (17)0.0003 (14)0.0083 (14)0.0007 (14)
C20.0551 (19)0.0413 (16)0.061 (2)0.0132 (14)0.0013 (15)0.0004 (14)
C30.0483 (17)0.0399 (17)0.0536 (18)0.0074 (14)0.0072 (14)0.0026 (14)
C40.060 (2)0.0515 (19)0.0530 (18)0.0147 (17)0.0017 (16)0.0076 (15)
C50.0415 (17)0.0454 (19)0.073 (2)0.0072 (14)0.0014 (16)0.0157 (18)
C60.0528 (16)0.0402 (16)0.0508 (17)0.0020 (15)0.0040 (15)0.0039 (13)
Geometric parameters (Å, º) top
Ag1—N12.112 (2)N4—C41.326 (4)
Ag1—N32.116 (2)N4—C51.350 (5)
O1—N51.240 (3)N4—H40.8600
O2—N51.225 (3)C1—H10.9300
O3—N51.238 (3)C2—C31.348 (4)
N1—C11.305 (4)C2—H2A0.9300
N1—C31.371 (4)C3—H30.9300
N2—C11.328 (4)C4—H4A0.9300
N2—C21.355 (4)C5—C61.362 (5)
N2—H20.8600C5—H50.9300
N3—C41.305 (4)C6—H60.9300
N3—C61.373 (4)
N1—Ag1—N3172.62 (10)N1—C1—H1124.4
C1—N1—C3105.8 (3)N2—C1—H1124.4
C1—N1—Ag1126.3 (2)C3—C2—N2106.1 (3)
C3—N1—Ag1127.5 (2)C3—C2—H2A126.9
C1—N2—C2107.7 (3)N2—C2—H2A126.9
C1—N2—H2126.1C2—C3—N1109.1 (3)
C2—N2—H2126.1C2—C3—H3125.4
C4—N3—C6106.1 (3)N1—C3—H3125.4
C4—N3—Ag1122.4 (2)N3—C4—N4111.4 (3)
C6—N3—Ag1131.3 (2)N3—C4—H4A124.3
C4—N4—C5107.8 (3)N4—C4—H4A124.3
C4—N4—H4126.1N4—C5—C6106.4 (3)
C5—N4—H4126.1N4—C5—H5126.8
O2—N5—O3120.1 (3)C6—C5—H5126.8
O2—N5—O1121.5 (3)C5—C6—N3108.2 (3)
O3—N5—O1118.4 (3)C5—C6—H6125.9
N1—C1—N2111.2 (3)N3—C6—H6125.9
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O1i0.862.032.879 (4)171
N4—H4···O30.862.002.853 (5)174
Symmetry code: (i) x2, y+1, z.

Experimental details

Crystal data
Chemical formula[Ag(C3H4N2)2)]NO3
Mr306.04
Crystal system, space groupOrthorhombic, P212121
Temperature (K)298
a, b, c (Å)4.9941 (4), 10.9250 (8), 18.0729 (12)
V3)986.07 (13)
Z4
Radiation typeMo Kα
µ (mm1)2.04
Crystal size (mm)0.22 × 0.20 × 0.16
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2002)
Tmin, Tmax0.630, 0.720
No. of measured, independent and
observed [I > 2σ(I)] reflections
5440, 2266, 2175
Rint0.034
(sin θ/λ)max1)0.652
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.023, 0.054, 1.06
No. of reflections2266
No. of parameters137
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.34, 0.24
Absolute structureFlack (1983), with 896 Friedel pairs
Absolute structure parameter0.01 (4)

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1998), SHELXTL.

Selected geometric parameters (Å, º) top
Ag1—N12.112 (2)Ag1—N32.116 (2)
N1—Ag1—N3172.62 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O1i0.862.032.879 (4)171
N4—H4···O30.862.002.853 (5)174
Symmetry code: (i) x2, y+1, z.
 

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