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In the title compound, [Ag(C6H9N3O3)2]NO3, the Ag atom is bicoordinated in a distorted linear configuration by two 1-(2-hydroxy­ethyl)-2-methyl-5-nitro­imidazole ligands through one of the N atoms. The dihedral angle between the two imidazole rings is 16.1 (2)°. The O atoms of the nitrate anion are disordered over two positions; the site occupancy factors are 0.8 and 0.2. The ions are ­connected by C—H...O inter­actions, while two weak intra­molecular C—H...O inter­actions producing an S(6) ring motif are observed. The nitrate anion is linked to the hydroxyl groups of two neighbouring cations by O—H...O hydrogen bonds. The ions are packed into infinite chains along the [100] direction.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808009860/ez2123sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536808009860/ez2123Isup2.hkl
Contains datablock I

CCDC reference: 688824

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.002 Å
  • Disorder in main residue
  • R factor = 0.024
  • wR factor = 0.060
  • Data-to-parameter ratio = 22.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.74 mm PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 100 Deg. PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 4 PLAT230_ALERT_2_C Hirshfeld Test Diff for O9A - O8B .. 5.92 su PLAT301_ALERT_3_C Main Residue Disorder ......................... 9.00 Perc. PLAT432_ALERT_2_C Short Inter X...Y Contact O7A .. C1 .. 2.98 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 1 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 34.60 Deg. O9B -N7 -O7A 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 41.90 Deg. O9A -N7 -O8B 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 10 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Nitroimidazole derivatives are of special interest due to their chemical and pharmacological properties. Nitroimidazoles are generally known as antiprotozoic and radiosensitizing drugs (Edwards, 1981). (1-(2-hydroxyethyl)-2-methyl-5-nitroimidazole), known as metronidazole in pharmaceuticals, is a widely used antibacterial drug (Credito et al., 2000; Mendz & Megraud, 2002). The structure of the title compound (I) has been determined to examine the influence of the coordination of silver on the geometry of the heterocycle.

The structure consists of two 1-(2-hydroxyethyl)2-methyl-5-nitroimidazole ligands coordinating to the silver through the N atoms in a distorted linear configuration, indicated by the N3—Ag1—N1 angle of 165.34 (4) °. The bond lengths of Ag1—N3 = 2.147 (11) Å and Ag1—N1 = 2.148 (11) Å, are comparable to the values reported for similar silver coordinated complexes (Tong & Chen, 2000; Ni et al., 2003; You & Zhu, 2004; Gao et al., 2004). The bond lengths of the heterocyclic five membered rings are comparable with the values found in 1-(2-hydroxyethyl)-2-methyl-5-nitroimidazole in its un-coordinated form (Blaton et al., 1979), iodometronidazole (Yang et al., 2005), and chlorometronidazole (Pi et al., 2005).

Both the hydroxyl oxygen atoms, O1 and O4, attached to the imidazole rings are twisted from the mean plane, with O1–C9–C8–N2 and O4–C11–C10–N4 torsion angles being -66.96 (14)° and -71.9 (14)° respectively. The nitro groups attached to the imidazole rings are slightly twisted, with O3—N5—C5—C4 and O6—N6—C2—C3 torsion angles of -10.8 (2)° and -13.3 (2)° respectively. Both imidazole rings are essentially planar, with the maximum deviation from planarity being 0.007 (1) Å for atom C1 and 0.003 (2) Å for atom N2. The nitrate anion is disordered over two positions with site occupancies of 0.8:0.2. The molecules in the asymmetric unit are interconnected by C—H···O hydrogen bonds. Intramolecular C—H···O hydrogen bonding results in an S(6) a ring motif, while two oxygen atoms of the major component of the disordered nitrate anion form C—H···O interations with the cation, forming an R22(10) motif (Fig. 1). The nitrate ions are linked to the hydroxyl groups on neighbouring cations by O—H···O hydrogen bonds. The molecules are packed into infinite one dimensional chains along the [1 0 0] direction.

Related literature top

For related literature regarding pharmaceutical uses of nitroimidazole derivatives, see: Credito et al. (2000); Edwards (1981); Mendz & Megraud (2002). For comparable crystal structures, see: Blaton et al. (1979); Gao et al. (2004); Ni et al. (2003); Pi et al. (2005); Tong & Chen (2000); Yang et al. (2005); You & Zhu (2004).

Experimental top

1-(2-hydroxyethyl)2-methyl-5-nitroimidazole) (0.350 g) [ALDRICH] was dissolved in 25 ml hot ethanol and silver nitrate [Sigma] (0.150 g) was dissolved in 20 ml ammonia solution in the molar ratio 2:1. These two solutions were mixed and heated under reflux for 48 h at a temperature of 363 K. Colourless plate shaped crystals were obtained after a month upon slow evaporation of the solvent.

Refinement top

After confirming their presence in the difference map, all H atoms were placed in calculated positions [C—H = 0.93 Å, CH3 = 0.96 Å CH2= 0.97Å and O—H = 0.86Å and refined using a riding model, with Uiso(H) = 1.2Ueq(C,O) and Uiso(H) = -1.5Ueq(methyl)]. The ratio of the occupancies for the major and minor components of the disordered nitro group O atoms were refined to 0.786 (3):0.214 (3). In the final refinement, this ratio was fixed at 0.8:0.2.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound, showing 50% probability displacement ellipsoids and the atomic numbering. Hydrogen bonds are shown as dashed lines.
[Figure 2] Fig. 2. The crystal packing of the title compound, viewed down the b axis. Hydrogen bonds are shown as dashed lines.
Bis[1-(2-hydroxyethyl)-2-methyl-5-nitro-1H-imidazole-κN3]silver(I) nitrate top
Crystal data top
[Ag(C6H9N3O3)2]NO3Z = 2
Mr = 512.2F(000) = 516
Triclinic, P1Dx = 1.882 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.6912 (1) ÅCell parameters from 9959 reflections
b = 11.6846 (3) Åθ = 3.2–37.8°
c = 12.9052 (3) ŵ = 1.18 mm1
α = 63.707 (1)°T = 100 K
β = 88.820 (1)°Plate, colourless
γ = 87.486 (1)°0.74 × 0.22 × 0.1 mm
V = 903.72 (3) Å3
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
5958 reflections with I > 2σ(I)
ϕ and ω scansRint = 0.026
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
θmax = 32.5°, θmin = 2.0°
Tmin = 0.476, Tmax = 0.892h = 1010
20384 measured reflectionsk = 1717
6509 independent reflectionsl = 1919
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.024 w = 1/[σ2(Fo2) + (0.0281P)2 + 0.2414P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.059(Δ/σ)max = 0.005
S = 1.08Δρmax = 0.58 e Å3
6509 reflectionsΔρmin = 0.65 e Å3
291 parameters
Crystal data top
[Ag(C6H9N3O3)2]NO3γ = 87.486 (1)°
Mr = 512.2V = 903.72 (3) Å3
Triclinic, P1Z = 2
a = 6.6912 (1) ÅMo Kα radiation
b = 11.6846 (3) ŵ = 1.18 mm1
c = 12.9052 (3) ÅT = 100 K
α = 63.707 (1)°0.74 × 0.22 × 0.1 mm
β = 88.820 (1)°
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
6509 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
5958 reflections with I > 2σ(I)
Tmin = 0.476, Tmax = 0.892Rint = 0.026
20384 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0240 restraints
wR(F2) = 0.059H-atom parameters constrained
S = 1.08Δρmax = 0.58 e Å3
6509 reflectionsΔρmin = 0.65 e Å3
291 parameters
Special details top

Geometry. Experimental. The low-temperature data was collected with the Oxford Crysosystem Cobra low-temperature attachement.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Ag10.247504 (15)0.147593 (9)1.004773 (8)0.01643 (3)
O10.93316 (17)0.44665 (10)0.82229 (9)0.0223 (2)
H1010.90520.37850.85940.027*
O20.70475 (17)0.41493 (11)0.50145 (9)0.0243 (2)
O30.62322 (18)0.21652 (11)0.56769 (10)0.0250 (2)
O40.46849 (17)0.21717 (10)1.24656 (9)0.0214 (2)
H1O40.42880.20021.20030.026*
O50.18196 (16)0.16629 (10)1.51008 (8)0.0191 (2)
O60.10089 (17)0.26774 (9)1.40801 (9)0.0211 (2)
N10.39023 (17)0.26342 (10)0.84333 (9)0.01355 (19)
N20.56794 (17)0.41644 (10)0.71061 (9)0.01301 (19)
N30.10790 (17)0.07543 (11)1.17193 (9)0.0136 (2)
N40.07227 (16)0.06598 (10)1.32188 (9)0.01194 (19)
N50.63543 (18)0.31651 (12)0.57702 (10)0.0168 (2)
N60.11678 (17)0.16962 (11)1.42100 (9)0.0139 (2)
C10.02601 (19)0.14301 (12)1.22443 (11)0.0127 (2)
C20.0527 (2)0.05563 (12)1.32798 (11)0.0124 (2)
C30.0586 (2)0.04857 (12)1.23573 (11)0.0137 (2)
H3A0.09470.11651.21920.016*
C40.4512 (2)0.22327 (12)0.76340 (11)0.0140 (2)
H4A0.42260.14550.76450.017*
C50.5613 (2)0.31599 (12)0.68117 (11)0.0135 (2)
C60.46316 (19)0.38035 (12)0.80999 (11)0.0133 (2)
C70.4302 (2)0.45784 (13)0.87398 (13)0.0190 (3)
H7A0.31410.42960.92230.028*
H7B0.41030.54610.82010.028*
H7C0.54490.44810.92110.028*
C80.6977 (2)0.52691 (12)0.66141 (12)0.0170 (2)
H8A0.64910.59130.6850.02*
H8B0.69310.56420.57770.02*
C90.9125 (2)0.48636 (14)0.70209 (13)0.0188 (3)
H9A0.95640.41680.68440.023*
H9B0.99820.55740.66030.023*
C100.2072 (2)0.10938 (13)1.39020 (11)0.0147 (2)
H10A0.17020.19341.3790.018*
H10B0.19190.05131.47160.018*
C110.4241 (2)0.11526 (13)1.35576 (12)0.0165 (2)
H11A0.45410.03541.35450.02*
H11B0.50930.12451.41350.02*
C120.0442 (2)0.28233 (13)1.18237 (13)0.0182 (3)
H12A0.09930.31831.10570.027*
H12B0.13060.29771.2330.027*
H12C0.08560.32131.18120.027*
N70.25847 (17)0.14402 (10)0.98555 (9)0.0148 (2)
O7A0.2995 (2)0.22646 (13)0.95060 (13)0.0197 (3)0.8
O8A0.1492 (2)0.17829 (13)1.07672 (11)0.0195 (2)0.8
O9A0.3251 (2)0.03721 (13)0.93965 (13)0.0255 (3)0.8
O7B0.1786 (8)0.0844 (5)1.0334 (4)0.0190 (10)0.2
O8B0.3686 (7)0.0715 (5)0.8893 (4)0.0154 (9)0.2
O9B0.2298 (9)0.2500 (5)0.9990 (5)0.0163 (9)0.2
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ag10.01378 (5)0.01905 (5)0.01297 (5)0.00266 (4)0.00451 (3)0.00392 (4)
O10.0242 (5)0.0180 (5)0.0232 (5)0.0036 (4)0.0036 (4)0.0073 (4)
O20.0234 (5)0.0286 (6)0.0147 (4)0.0036 (4)0.0057 (4)0.0041 (4)
O30.0304 (6)0.0284 (6)0.0222 (5)0.0004 (5)0.0003 (4)0.0168 (4)
O40.0219 (5)0.0204 (5)0.0198 (5)0.0055 (4)0.0027 (4)0.0075 (4)
O50.0193 (5)0.0222 (5)0.0135 (4)0.0019 (4)0.0060 (4)0.0060 (4)
O60.0281 (6)0.0133 (4)0.0208 (5)0.0021 (4)0.0040 (4)0.0065 (4)
N10.0130 (5)0.0130 (5)0.0132 (5)0.0023 (4)0.0022 (4)0.0044 (4)
N20.0127 (5)0.0115 (4)0.0127 (4)0.0016 (4)0.0002 (4)0.0033 (4)
N30.0131 (5)0.0140 (5)0.0124 (4)0.0002 (4)0.0023 (4)0.0049 (4)
N40.0111 (5)0.0135 (5)0.0121 (4)0.0002 (4)0.0009 (4)0.0065 (4)
N50.0141 (5)0.0230 (6)0.0128 (5)0.0005 (4)0.0001 (4)0.0074 (4)
N60.0119 (5)0.0149 (5)0.0133 (5)0.0005 (4)0.0008 (4)0.0048 (4)
C10.0107 (5)0.0141 (5)0.0134 (5)0.0006 (4)0.0004 (4)0.0061 (4)
C20.0136 (5)0.0114 (5)0.0115 (5)0.0006 (4)0.0013 (4)0.0044 (4)
C30.0148 (6)0.0125 (5)0.0126 (5)0.0015 (4)0.0013 (4)0.0046 (4)
C40.0146 (6)0.0137 (5)0.0137 (5)0.0022 (4)0.0006 (4)0.0059 (4)
C50.0136 (5)0.0151 (5)0.0115 (5)0.0016 (4)0.0008 (4)0.0056 (4)
C60.0119 (5)0.0122 (5)0.0142 (5)0.0002 (4)0.0003 (4)0.0044 (4)
C70.0205 (6)0.0159 (6)0.0227 (6)0.0001 (5)0.0030 (5)0.0106 (5)
C80.0173 (6)0.0124 (5)0.0172 (6)0.0055 (5)0.0023 (5)0.0026 (4)
C90.0152 (6)0.0185 (6)0.0232 (6)0.0056 (5)0.0028 (5)0.0094 (5)
C100.0154 (6)0.0175 (6)0.0135 (5)0.0011 (5)0.0022 (5)0.0091 (5)
C110.0138 (6)0.0183 (6)0.0167 (6)0.0007 (5)0.0030 (5)0.0072 (5)
C120.0188 (6)0.0136 (5)0.0221 (6)0.0023 (5)0.0027 (5)0.0078 (5)
N70.0136 (5)0.0157 (5)0.0162 (5)0.0004 (4)0.0016 (4)0.0082 (4)
O7A0.0249 (7)0.0191 (6)0.0181 (6)0.0024 (5)0.0005 (6)0.0111 (5)
O8A0.0195 (6)0.0248 (7)0.0148 (5)0.0011 (5)0.0033 (5)0.0095 (5)
O9A0.0274 (7)0.0148 (6)0.0300 (7)0.0050 (5)0.0031 (6)0.0059 (5)
O7B0.018 (2)0.026 (3)0.020 (2)0.003 (2)0.0041 (19)0.017 (2)
O8B0.013 (2)0.016 (2)0.013 (2)0.0043 (17)0.0042 (17)0.0027 (17)
O9B0.023 (3)0.010 (2)0.012 (2)0.0014 (19)0.001 (2)0.0019 (17)
Geometric parameters (Å, º) top
Ag1—N32.1475 (11)C4—C51.3646 (17)
Ag1—N12.1489 (11)C4—H4A0.93
O1—C91.4165 (18)C6—C71.4791 (18)
O1—H1010.7548C7—H7A0.96
O2—N51.2342 (15)C7—H7B0.96
O3—N51.2327 (16)C7—H7C0.96
O4—C111.4112 (17)C8—C91.522 (2)
O4—H1O40.7478C8—H8A0.97
O5—N61.2372 (14)C8—H8B0.97
O6—N61.2299 (15)C9—H9A0.97
N1—C61.3487 (16)C9—H9B0.97
N1—C41.3583 (17)C10—C111.5160 (19)
N2—C61.3505 (16)C10—H10A0.97
N2—C51.3871 (16)C10—H10B0.97
N2—C81.4738 (16)C11—H11A0.97
N3—C11.3430 (16)C11—H11B0.97
N3—C31.3638 (16)C12—H12A0.96
N4—C11.3561 (16)C12—H12B0.96
N4—C21.3884 (16)C12—H12C0.96
N4—C101.4742 (16)N7—O9B1.195 (5)
N5—C51.4206 (17)N7—O7B1.219 (5)
N6—C21.4182 (16)N7—O9A1.2207 (17)
C1—C121.4803 (18)N7—O7A1.2503 (17)
C2—C31.3643 (17)N7—O8A1.2854 (16)
C3—H3A0.93N7—O8B1.374 (5)
N3—Ag1—N1165.34 (4)N2—C8—C9110.63 (11)
C9—O1—H101114.1N2—C8—H8A109.5
C11—O4—H1O4109.2C9—C8—H8A109.5
C6—N1—C4106.90 (10)N2—C8—H8B109.5
C6—N1—Ag1127.13 (9)C9—C8—H8B109.5
C4—N1—Ag1125.25 (9)H8A—C8—H8B108.1
C6—N2—C5105.98 (10)O1—C9—C8112.19 (11)
C6—N2—C8124.90 (11)O1—C9—H9A109.2
C5—N2—C8127.79 (11)C8—C9—H9A109.2
C1—N3—C3107.24 (10)O1—C9—H9B109.2
C1—N3—Ag1127.60 (9)C8—C9—H9B109.2
C3—N3—Ag1124.41 (9)H9A—C9—H9B107.9
C1—N4—C2105.63 (10)N4—C10—C11111.72 (11)
C1—N4—C10125.57 (11)N4—C10—H10A109.3
C2—N4—C10127.52 (10)C11—C10—H10A109.3
O3—N5—O2123.88 (12)N4—C10—H10B109.3
O3—N5—C5116.63 (11)C11—C10—H10B109.3
O2—N5—C5119.48 (12)H10A—C10—H10B107.9
O6—N6—O5123.70 (11)O4—C11—C10112.83 (11)
O6—N6—C2116.89 (11)O4—C11—H11A109
O5—N6—C2119.40 (11)C10—C11—H11A109
N3—C1—N4110.81 (11)O4—C11—H11B109
N3—C1—C12124.38 (11)C10—C11—H11B109
N4—C1—C12124.80 (11)H11A—C11—H11B107.8
C3—C2—N4108.17 (11)C1—C12—H12A109.5
C3—C2—N6125.67 (12)C1—C12—H12B109.5
N4—C2—N6125.76 (11)H12A—C12—H12B109.5
N3—C3—C2108.13 (11)C1—C12—H12C109.5
N3—C3—H3A125.9H12A—C12—H12C109.5
C2—C3—H3A125.9H12B—C12—H12C109.5
N1—C4—C5108.62 (11)O9B—N7—O7B129.1 (4)
N1—C4—H4A125.7O9B—N7—O9A157.0 (3)
C5—C4—H4A125.7O7B—N7—O9A73.6 (3)
C4—C5—N2107.74 (11)O9B—N7—O7A34.6 (3)
C4—C5—N5126.13 (12)O7B—N7—O7A163.2 (3)
N2—C5—N5125.74 (11)O9A—N7—O7A122.53 (14)
N1—C6—N2110.75 (11)O9B—N7—O8A82.5 (3)
N1—C6—C7124.08 (12)O7B—N7—O8A47.6 (3)
N2—C6—C7125.16 (11)O9A—N7—O8A120.45 (13)
C6—C7—H7A109.5O7A—N7—O8A116.95 (13)
C6—C7—H7B109.5O9B—N7—O8B115.2 (4)
H7A—C7—H7B109.5O7B—N7—O8B114.5 (4)
C6—C7—H7C109.5O9A—N7—O8B41.9 (2)
H7A—C7—H7C109.5O7A—N7—O8B80.9 (2)
H7B—C7—H7C109.5O8A—N7—O8B162.1 (2)
N3—Ag1—N1—C68.8 (2)Ag1—N1—C4—C5170.95 (9)
N3—Ag1—N1—C4177.85 (15)N1—C4—C5—N20.29 (16)
N1—Ag1—N3—C117.4 (2)N1—C4—C5—N5173.38 (13)
N1—Ag1—N3—C3173.76 (15)C6—N2—C5—C40.52 (15)
C3—N3—C1—N41.10 (15)C8—N2—C5—C4167.74 (12)
Ag1—N3—C1—N4171.44 (9)C6—N2—C5—N5173.64 (13)
C3—N3—C1—C12179.92 (13)C8—N2—C5—N519.1 (2)
Ag1—N3—C1—C129.6 (2)O3—N5—C5—C410.8 (2)
C2—N4—C1—N31.28 (15)O2—N5—C5—C4168.30 (14)
C10—N4—C1—N3169.09 (12)O3—N5—C5—N2177.36 (13)
C2—N4—C1—C12179.75 (13)O2—N5—C5—N23.6 (2)
C10—N4—C1—C1211.9 (2)C4—N1—C6—N20.39 (15)
C1—N4—C2—C30.96 (15)Ag1—N1—C6—N2171.07 (9)
C10—N4—C2—C3168.46 (12)C4—N1—C6—C7179.94 (13)
C1—N4—C2—N6174.09 (13)Ag1—N1—C6—C79.39 (19)
C10—N4—C2—N618.4 (2)C5—N2—C6—N10.57 (15)
O6—N6—C2—C313.3 (2)C8—N2—C6—N1168.26 (12)
O5—N6—C2—C3165.71 (13)C5—N2—C6—C7179.89 (13)
O6—N6—C2—N4174.73 (13)C8—N2—C6—C712.2 (2)
O5—N6—C2—N46.2 (2)C6—N2—C8—C992.52 (15)
C1—N3—C3—C20.46 (16)C5—N2—C8—C972.45 (17)
Ag1—N3—C3—C2171.18 (9)N2—C8—C9—O166.96 (14)
N4—C2—C3—N30.32 (16)C1—N4—C10—C1194.80 (15)
N6—C2—C3—N3173.46 (12)C2—N4—C10—C1170.35 (17)
C6—N1—C4—C50.05 (15)N4—C10—C11—O471.90 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H101···O9Bi0.752.012.685 (5)150
O1—H101···O8Ai0.752.152.8872 (17)164
O4—H1O4···O7Aii0.752.022.7225 (18)158
O4—H1O4···O8Bii0.752.292.985 (5)156
C3—H3A···O8A0.932.273.0820145
C4—H4A···O9A0.932.423.0269122
C8—H8B···O20.972.352.891 (2)115
C10—H10B···O50.972.362.888 (2)113
Symmetry codes: (i) x+1, y, z+2; (ii) x, y, z+2.

Experimental details

Crystal data
Chemical formula[Ag(C6H9N3O3)2]NO3
Mr512.2
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)6.6912 (1), 11.6846 (3), 12.9052 (3)
α, β, γ (°)63.707 (1), 88.820 (1), 87.486 (1)
V3)903.72 (3)
Z2
Radiation typeMo Kα
µ (mm1)1.18
Crystal size (mm)0.74 × 0.22 × 0.1
Data collection
DiffractometerBruker SMART APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.476, 0.892
No. of measured, independent and
observed [I > 2σ(I)] reflections
20384, 6509, 5958
Rint0.026
(sin θ/λ)max1)0.756
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.024, 0.059, 1.08
No. of reflections6509
No. of parameters291
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.58, 0.65

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H101···O9Bi0.752.012.685 (5)149.5
O1—H101···O8Ai0.752.152.8872 (17)164
O4—H1O4···O7Aii0.752.022.7225 (18)157.8
O4—H1O4···O8Bii0.752.292.985 (5)155.9
C3—H3A···O8A0.932.273.0820145
C4—H4A···O9A0.932.423.0269122
C8—H8B···O20.972.352.891 (2)115
C10—H10B···O50.972.362.888 (2)113
Symmetry codes: (i) x+1, y, z+2; (ii) x, y, z+2.
 

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