metal-organic compounds
Bis[1-(2-hydroxyethyl)-2-methyl-5-nitro-1H-imidazole-κN3]silver(I) nitrate
aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bDepartment of Physics, National Institute of Technology, Tiruchirappalli 620 015, India
*Correspondence e-mail: hkfun@usm.my
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.
Related literature
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
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2005); cell APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).
Supporting information
10.1107/S1600536808009860/ez2123sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808009860/ez2123Isup2.hkl
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.
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
this ratio was fixed at 0.8:0.2.Data collection: APEX2 (Bruker, 2005); cell
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).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. | |
Fig. 2. The crystal packing of the title compound, viewed down the b axis. Hydrogen bonds are shown as dashed lines. |
[Ag(C6H9N3O3)2]NO3 | Z = 2 |
Mr = 512.2 | F(000) = 516 |
Triclinic, P1 | Dx = 1.882 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.6912 (1) Å | Cell parameters from 9959 reflections |
b = 11.6846 (3) Å | θ = 3.2–37.8° |
c = 12.9052 (3) Å | µ = 1.18 mm−1 |
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 |
Bruker SMART APEXII CCD area-detector diffractometer | 5958 reflections with I > 2σ(I) |
ϕ and ω scans | Rint = 0.026 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | θmax = 32.5°, θmin = 2.0° |
Tmin = 0.476, Tmax = 0.892 | h = −10→10 |
20384 measured reflections | k = −17→17 |
6509 independent reflections | l = −19→19 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-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 = 1.08 | Δρmax = 0.58 e Å−3 |
6509 reflections | Δρmin = −0.65 e Å−3 |
291 parameters |
[Ag(C6H9N3O3)2]NO3 | γ = 87.486 (1)° |
Mr = 512.2 | V = 903.72 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 6.6912 (1) Å | Mo Kα radiation |
b = 11.6846 (3) Å | µ = 1.18 mm−1 |
c = 12.9052 (3) Å | T = 100 K |
α = 63.707 (1)° | 0.74 × 0.22 × 0.1 mm |
β = 88.820 (1)° |
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 = 0.892 | Rint = 0.026 |
20384 measured reflections |
R[F2 > 2σ(F2)] = 0.024 | 0 restraints |
wR(F2) = 0.059 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.58 e Å−3 |
6509 reflections | Δρmin = −0.65 e Å−3 |
291 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Ag1 | 0.247504 (15) | 0.147593 (9) | 1.004773 (8) | 0.01643 (3) | |
O1 | 0.93316 (17) | 0.44665 (10) | 0.82229 (9) | 0.0223 (2) | |
H101 | 0.9052 | 0.3785 | 0.8594 | 0.027* | |
O2 | 0.70475 (17) | 0.41493 (11) | 0.50145 (9) | 0.0243 (2) | |
O3 | 0.62322 (18) | 0.21652 (11) | 0.56769 (10) | 0.0250 (2) | |
O4 | −0.46849 (17) | 0.21717 (10) | 1.24656 (9) | 0.0214 (2) | |
H1O4 | −0.4288 | 0.2002 | 1.2003 | 0.026* | |
O5 | −0.18196 (16) | −0.16629 (10) | 1.51008 (8) | 0.0191 (2) | |
O6 | −0.10089 (17) | −0.26774 (9) | 1.40801 (9) | 0.0211 (2) | |
N1 | 0.39023 (17) | 0.26342 (10) | 0.84333 (9) | 0.01355 (19) | |
N2 | 0.56794 (17) | 0.41644 (10) | 0.71061 (9) | 0.01301 (19) | |
N3 | 0.10790 (17) | 0.07543 (11) | 1.17193 (9) | 0.0136 (2) | |
N4 | −0.07227 (16) | 0.06598 (10) | 1.32188 (9) | 0.01194 (19) | |
N5 | 0.63543 (18) | 0.31651 (12) | 0.57702 (10) | 0.0168 (2) | |
N6 | −0.11678 (17) | −0.16962 (11) | 1.42100 (9) | 0.0139 (2) | |
C1 | 0.02601 (19) | 0.14301 (12) | 1.22443 (11) | 0.0127 (2) | |
C2 | −0.0527 (2) | −0.05563 (12) | 1.32798 (11) | 0.0124 (2) | |
C3 | 0.0586 (2) | −0.04857 (12) | 1.23573 (11) | 0.0137 (2) | |
H3A | 0.0947 | −0.1165 | 1.2192 | 0.016* | |
C4 | 0.4512 (2) | 0.22327 (12) | 0.76340 (11) | 0.0140 (2) | |
H4A | 0.4226 | 0.1455 | 0.7645 | 0.017* | |
C5 | 0.5613 (2) | 0.31599 (12) | 0.68117 (11) | 0.0135 (2) | |
C6 | 0.46316 (19) | 0.38035 (12) | 0.80999 (11) | 0.0133 (2) | |
C7 | 0.4302 (2) | 0.45784 (13) | 0.87398 (13) | 0.0190 (3) | |
H7A | 0.3141 | 0.4296 | 0.9223 | 0.028* | |
H7B | 0.4103 | 0.5461 | 0.8201 | 0.028* | |
H7C | 0.5449 | 0.4481 | 0.9211 | 0.028* | |
C8 | 0.6977 (2) | 0.52691 (12) | 0.66141 (12) | 0.0170 (2) | |
H8A | 0.6491 | 0.5913 | 0.685 | 0.02* | |
H8B | 0.6931 | 0.5642 | 0.5777 | 0.02* | |
C9 | 0.9125 (2) | 0.48636 (14) | 0.70209 (13) | 0.0188 (3) | |
H9A | 0.9564 | 0.4168 | 0.6844 | 0.023* | |
H9B | 0.9982 | 0.5574 | 0.6603 | 0.023* | |
C10 | −0.2072 (2) | 0.10938 (13) | 1.39020 (11) | 0.0147 (2) | |
H10A | −0.1702 | 0.1934 | 1.379 | 0.018* | |
H10B | −0.1919 | 0.0513 | 1.4716 | 0.018* | |
C11 | −0.4241 (2) | 0.11526 (13) | 1.35576 (12) | 0.0165 (2) | |
H11A | −0.4541 | 0.0354 | 1.3545 | 0.02* | |
H11B | −0.5093 | 0.1245 | 1.4135 | 0.02* | |
C12 | 0.0442 (2) | 0.28233 (13) | 1.18237 (13) | 0.0182 (3) | |
H12A | 0.0993 | 0.3183 | 1.1057 | 0.027* | |
H12B | 0.1306 | 0.2977 | 1.233 | 0.027* | |
H12C | −0.0856 | 0.3213 | 1.1812 | 0.027* | |
N7 | 0.25847 (17) | −0.14402 (10) | 0.98555 (9) | 0.0148 (2) | |
O7A | 0.2995 (2) | −0.22646 (13) | 0.95060 (13) | 0.0197 (3) | 0.8 |
O8A | 0.1492 (2) | −0.17829 (13) | 1.07672 (11) | 0.0195 (2) | 0.8 |
O9A | 0.3251 (2) | −0.03721 (13) | 0.93965 (13) | 0.0255 (3) | 0.8 |
O7B | 0.1786 (8) | −0.0844 (5) | 1.0334 (4) | 0.0190 (10) | 0.2 |
O8B | 0.3686 (7) | −0.0715 (5) | 0.8893 (4) | 0.0154 (9) | 0.2 |
O9B | 0.2298 (9) | −0.2500 (5) | 0.9990 (5) | 0.0163 (9) | 0.2 |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ag1 | 0.01378 (5) | 0.01905 (5) | 0.01297 (5) | −0.00266 (4) | 0.00451 (3) | −0.00392 (4) |
O1 | 0.0242 (5) | 0.0180 (5) | 0.0232 (5) | −0.0036 (4) | −0.0036 (4) | −0.0073 (4) |
O2 | 0.0234 (5) | 0.0286 (6) | 0.0147 (4) | −0.0036 (4) | 0.0057 (4) | −0.0041 (4) |
O3 | 0.0304 (6) | 0.0284 (6) | 0.0222 (5) | −0.0004 (5) | 0.0003 (4) | −0.0168 (4) |
O4 | 0.0219 (5) | 0.0204 (5) | 0.0198 (5) | 0.0055 (4) | −0.0027 (4) | −0.0075 (4) |
O5 | 0.0193 (5) | 0.0222 (5) | 0.0135 (4) | −0.0019 (4) | 0.0060 (4) | −0.0060 (4) |
O6 | 0.0281 (6) | 0.0133 (4) | 0.0208 (5) | −0.0021 (4) | 0.0040 (4) | −0.0065 (4) |
N1 | 0.0130 (5) | 0.0130 (5) | 0.0132 (5) | −0.0023 (4) | 0.0022 (4) | −0.0044 (4) |
N2 | 0.0127 (5) | 0.0115 (4) | 0.0127 (4) | −0.0016 (4) | 0.0002 (4) | −0.0033 (4) |
N3 | 0.0131 (5) | 0.0140 (5) | 0.0124 (4) | −0.0002 (4) | 0.0023 (4) | −0.0049 (4) |
N4 | 0.0111 (5) | 0.0135 (5) | 0.0121 (4) | −0.0002 (4) | 0.0009 (4) | −0.0065 (4) |
N5 | 0.0141 (5) | 0.0230 (6) | 0.0128 (5) | 0.0005 (4) | −0.0001 (4) | −0.0074 (4) |
N6 | 0.0119 (5) | 0.0149 (5) | 0.0133 (5) | −0.0005 (4) | 0.0008 (4) | −0.0048 (4) |
C1 | 0.0107 (5) | 0.0141 (5) | 0.0134 (5) | −0.0006 (4) | 0.0004 (4) | −0.0061 (4) |
C2 | 0.0136 (5) | 0.0114 (5) | 0.0115 (5) | −0.0006 (4) | 0.0013 (4) | −0.0044 (4) |
C3 | 0.0148 (6) | 0.0125 (5) | 0.0126 (5) | 0.0015 (4) | 0.0013 (4) | −0.0046 (4) |
C4 | 0.0146 (6) | 0.0137 (5) | 0.0137 (5) | −0.0022 (4) | 0.0006 (4) | −0.0059 (4) |
C5 | 0.0136 (5) | 0.0151 (5) | 0.0115 (5) | −0.0016 (4) | 0.0008 (4) | −0.0056 (4) |
C6 | 0.0119 (5) | 0.0122 (5) | 0.0142 (5) | −0.0002 (4) | 0.0003 (4) | −0.0044 (4) |
C7 | 0.0205 (6) | 0.0159 (6) | 0.0227 (6) | −0.0001 (5) | 0.0030 (5) | −0.0106 (5) |
C8 | 0.0173 (6) | 0.0124 (5) | 0.0172 (6) | −0.0055 (5) | 0.0023 (5) | −0.0026 (4) |
C9 | 0.0152 (6) | 0.0185 (6) | 0.0232 (6) | −0.0056 (5) | 0.0028 (5) | −0.0094 (5) |
C10 | 0.0154 (6) | 0.0175 (6) | 0.0135 (5) | 0.0011 (5) | 0.0022 (5) | −0.0091 (5) |
C11 | 0.0138 (6) | 0.0183 (6) | 0.0167 (6) | 0.0007 (5) | 0.0030 (5) | −0.0072 (5) |
C12 | 0.0188 (6) | 0.0136 (5) | 0.0221 (6) | −0.0023 (5) | 0.0027 (5) | −0.0078 (5) |
N7 | 0.0136 (5) | 0.0157 (5) | 0.0162 (5) | 0.0004 (4) | −0.0016 (4) | −0.0082 (4) |
O7A | 0.0249 (7) | 0.0191 (6) | 0.0181 (6) | 0.0024 (5) | −0.0005 (6) | −0.0111 (5) |
O8A | 0.0195 (6) | 0.0248 (7) | 0.0148 (5) | −0.0011 (5) | 0.0033 (5) | −0.0095 (5) |
O9A | 0.0274 (7) | 0.0148 (6) | 0.0300 (7) | −0.0050 (5) | 0.0031 (6) | −0.0059 (5) |
O7B | 0.018 (2) | 0.026 (3) | 0.020 (2) | 0.003 (2) | 0.0041 (19) | −0.017 (2) |
O8B | 0.013 (2) | 0.016 (2) | 0.013 (2) | −0.0043 (17) | 0.0042 (17) | −0.0027 (17) |
O9B | 0.023 (3) | 0.010 (2) | 0.012 (2) | −0.0014 (19) | 0.001 (2) | −0.0019 (17) |
Ag1—N3 | 2.1475 (11) | C4—C5 | 1.3646 (17) |
Ag1—N1 | 2.1489 (11) | C4—H4A | 0.93 |
O1—C9 | 1.4165 (18) | C6—C7 | 1.4791 (18) |
O1—H101 | 0.7548 | C7—H7A | 0.96 |
O2—N5 | 1.2342 (15) | C7—H7B | 0.96 |
O3—N5 | 1.2327 (16) | C7—H7C | 0.96 |
O4—C11 | 1.4112 (17) | C8—C9 | 1.522 (2) |
O4—H1O4 | 0.7478 | C8—H8A | 0.97 |
O5—N6 | 1.2372 (14) | C8—H8B | 0.97 |
O6—N6 | 1.2299 (15) | C9—H9A | 0.97 |
N1—C6 | 1.3487 (16) | C9—H9B | 0.97 |
N1—C4 | 1.3583 (17) | C10—C11 | 1.5160 (19) |
N2—C6 | 1.3505 (16) | C10—H10A | 0.97 |
N2—C5 | 1.3871 (16) | C10—H10B | 0.97 |
N2—C8 | 1.4738 (16) | C11—H11A | 0.97 |
N3—C1 | 1.3430 (16) | C11—H11B | 0.97 |
N3—C3 | 1.3638 (16) | C12—H12A | 0.96 |
N4—C1 | 1.3561 (16) | C12—H12B | 0.96 |
N4—C2 | 1.3884 (16) | C12—H12C | 0.96 |
N4—C10 | 1.4742 (16) | N7—O9B | 1.195 (5) |
N5—C5 | 1.4206 (17) | N7—O7B | 1.219 (5) |
N6—C2 | 1.4182 (16) | N7—O9A | 1.2207 (17) |
C1—C12 | 1.4803 (18) | N7—O7A | 1.2503 (17) |
C2—C3 | 1.3643 (17) | N7—O8A | 1.2854 (16) |
C3—H3A | 0.93 | N7—O8B | 1.374 (5) |
N3—Ag1—N1 | 165.34 (4) | N2—C8—C9 | 110.63 (11) |
C9—O1—H101 | 114.1 | N2—C8—H8A | 109.5 |
C11—O4—H1O4 | 109.2 | C9—C8—H8A | 109.5 |
C6—N1—C4 | 106.90 (10) | N2—C8—H8B | 109.5 |
C6—N1—Ag1 | 127.13 (9) | C9—C8—H8B | 109.5 |
C4—N1—Ag1 | 125.25 (9) | H8A—C8—H8B | 108.1 |
C6—N2—C5 | 105.98 (10) | O1—C9—C8 | 112.19 (11) |
C6—N2—C8 | 124.90 (11) | O1—C9—H9A | 109.2 |
C5—N2—C8 | 127.79 (11) | C8—C9—H9A | 109.2 |
C1—N3—C3 | 107.24 (10) | O1—C9—H9B | 109.2 |
C1—N3—Ag1 | 127.60 (9) | C8—C9—H9B | 109.2 |
C3—N3—Ag1 | 124.41 (9) | H9A—C9—H9B | 107.9 |
C1—N4—C2 | 105.63 (10) | N4—C10—C11 | 111.72 (11) |
C1—N4—C10 | 125.57 (11) | N4—C10—H10A | 109.3 |
C2—N4—C10 | 127.52 (10) | C11—C10—H10A | 109.3 |
O3—N5—O2 | 123.88 (12) | N4—C10—H10B | 109.3 |
O3—N5—C5 | 116.63 (11) | C11—C10—H10B | 109.3 |
O2—N5—C5 | 119.48 (12) | H10A—C10—H10B | 107.9 |
O6—N6—O5 | 123.70 (11) | O4—C11—C10 | 112.83 (11) |
O6—N6—C2 | 116.89 (11) | O4—C11—H11A | 109 |
O5—N6—C2 | 119.40 (11) | C10—C11—H11A | 109 |
N3—C1—N4 | 110.81 (11) | O4—C11—H11B | 109 |
N3—C1—C12 | 124.38 (11) | C10—C11—H11B | 109 |
N4—C1—C12 | 124.80 (11) | H11A—C11—H11B | 107.8 |
C3—C2—N4 | 108.17 (11) | C1—C12—H12A | 109.5 |
C3—C2—N6 | 125.67 (12) | C1—C12—H12B | 109.5 |
N4—C2—N6 | 125.76 (11) | H12A—C12—H12B | 109.5 |
N3—C3—C2 | 108.13 (11) | C1—C12—H12C | 109.5 |
N3—C3—H3A | 125.9 | H12A—C12—H12C | 109.5 |
C2—C3—H3A | 125.9 | H12B—C12—H12C | 109.5 |
N1—C4—C5 | 108.62 (11) | O9B—N7—O7B | 129.1 (4) |
N1—C4—H4A | 125.7 | O9B—N7—O9A | 157.0 (3) |
C5—C4—H4A | 125.7 | O7B—N7—O9A | 73.6 (3) |
C4—C5—N2 | 107.74 (11) | O9B—N7—O7A | 34.6 (3) |
C4—C5—N5 | 126.13 (12) | O7B—N7—O7A | 163.2 (3) |
N2—C5—N5 | 125.74 (11) | O9A—N7—O7A | 122.53 (14) |
N1—C6—N2 | 110.75 (11) | O9B—N7—O8A | 82.5 (3) |
N1—C6—C7 | 124.08 (12) | O7B—N7—O8A | 47.6 (3) |
N2—C6—C7 | 125.16 (11) | O9A—N7—O8A | 120.45 (13) |
C6—C7—H7A | 109.5 | O7A—N7—O8A | 116.95 (13) |
C6—C7—H7B | 109.5 | O9B—N7—O8B | 115.2 (4) |
H7A—C7—H7B | 109.5 | O7B—N7—O8B | 114.5 (4) |
C6—C7—H7C | 109.5 | O9A—N7—O8B | 41.9 (2) |
H7A—C7—H7C | 109.5 | O7A—N7—O8B | 80.9 (2) |
H7B—C7—H7C | 109.5 | O8A—N7—O8B | 162.1 (2) |
N3—Ag1—N1—C6 | 8.8 (2) | Ag1—N1—C4—C5 | −170.95 (9) |
N3—Ag1—N1—C4 | 177.85 (15) | N1—C4—C5—N2 | −0.29 (16) |
N1—Ag1—N3—C1 | 17.4 (2) | N1—C4—C5—N5 | −173.38 (13) |
N1—Ag1—N3—C3 | −173.76 (15) | C6—N2—C5—C4 | 0.52 (15) |
C3—N3—C1—N4 | 1.10 (15) | C8—N2—C5—C4 | 167.74 (12) |
Ag1—N3—C1—N4 | 171.44 (9) | C6—N2—C5—N5 | 173.64 (13) |
C3—N3—C1—C12 | −179.92 (13) | C8—N2—C5—N5 | −19.1 (2) |
Ag1—N3—C1—C12 | −9.6 (2) | O3—N5—C5—C4 | −10.8 (2) |
C2—N4—C1—N3 | −1.28 (15) | O2—N5—C5—C4 | 168.30 (14) |
C10—N4—C1—N3 | −169.09 (12) | O3—N5—C5—N2 | 177.36 (13) |
C2—N4—C1—C12 | 179.75 (13) | O2—N5—C5—N2 | −3.6 (2) |
C10—N4—C1—C12 | 11.9 (2) | C4—N1—C6—N2 | 0.39 (15) |
C1—N4—C2—C3 | 0.96 (15) | Ag1—N1—C6—N2 | 171.07 (9) |
C10—N4—C2—C3 | 168.46 (12) | C4—N1—C6—C7 | 179.94 (13) |
C1—N4—C2—N6 | 174.09 (13) | Ag1—N1—C6—C7 | −9.39 (19) |
C10—N4—C2—N6 | −18.4 (2) | C5—N2—C6—N1 | −0.57 (15) |
O6—N6—C2—C3 | −13.3 (2) | C8—N2—C6—N1 | −168.26 (12) |
O5—N6—C2—C3 | 165.71 (13) | C5—N2—C6—C7 | 179.89 (13) |
O6—N6—C2—N4 | 174.73 (13) | C8—N2—C6—C7 | 12.2 (2) |
O5—N6—C2—N4 | −6.2 (2) | C6—N2—C8—C9 | 92.52 (15) |
C1—N3—C3—C2 | −0.46 (16) | C5—N2—C8—C9 | −72.45 (17) |
Ag1—N3—C3—C2 | −171.18 (9) | N2—C8—C9—O1 | −66.96 (14) |
N4—C2—C3—N3 | −0.32 (16) | C1—N4—C10—C11 | 94.80 (15) |
N6—C2—C3—N3 | −173.46 (12) | C2—N4—C10—C11 | −70.35 (17) |
C6—N1—C4—C5 | −0.05 (15) | N4—C10—C11—O4 | −71.90 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H101···O9Bi | 0.75 | 2.01 | 2.685 (5) | 150 |
O1—H101···O8Ai | 0.75 | 2.15 | 2.8872 (17) | 164 |
O4—H1O4···O7Aii | 0.75 | 2.02 | 2.7225 (18) | 158 |
O4—H1O4···O8Bii | 0.75 | 2.29 | 2.985 (5) | 156 |
C3—H3A···O8A | 0.93 | 2.27 | 3.0820 | 145 |
C4—H4A···O9A | 0.93 | 2.42 | 3.0269 | 122 |
C8—H8B···O2 | 0.97 | 2.35 | 2.891 (2) | 115 |
C10—H10B···O5 | 0.97 | 2.36 | 2.888 (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 |
Mr | 512.2 |
Crystal system, space group | Triclinic, 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) |
V (Å3) | 903.72 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.18 |
Crystal size (mm) | 0.74 × 0.22 × 0.1 |
Data collection | |
Diffractometer | Bruker SMART APEXII CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.476, 0.892 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 20384, 6509, 5958 |
Rint | 0.026 |
(sin θ/λ)max (Å−1) | 0.756 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.024, 0.059, 1.08 |
No. of reflections | 6509 |
No. of parameters | 291 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.58, −0.65 |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H101···O9Bi | 0.75 | 2.01 | 2.685 (5) | 149.5 |
O1—H101···O8Ai | 0.75 | 2.15 | 2.8872 (17) | 164 |
O4—H1O4···O7Aii | 0.75 | 2.02 | 2.7225 (18) | 157.8 |
O4—H1O4···O8Bii | 0.75 | 2.29 | 2.985 (5) | 155.9 |
C3—H3A···O8A | 0.93 | 2.27 | 3.0820 | 145 |
C4—H4A···O9A | 0.93 | 2.42 | 3.0269 | 122 |
C8—H8B···O2 | 0.97 | 2.35 | 2.891 (2) | 115 |
C10—H10B···O5 | 0.97 | 2.36 | 2.888 (2) | 113 |
Symmetry codes: (i) −x+1, −y, −z+2; (ii) −x, −y, −z+2. |
Footnotes
‡Permanent address: Department of Physics, Karunya University, Karunya Nagar, Coimbatore 641 114, India.
Acknowledgements
HKF and SRJ thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. SRJ thanks the Universiti Sains Malaysia for awarding a post-doctoral research fellowship.
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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.