Bis[1-(2-hydroxy-ethyl)-2-methyl-5-nitro-1H-imidazole-κN]silver(I) nitrate.

In the title compound, [Ag(C(6)H(9)N(3)O(3))(2)]NO(3), the Ag atom is bicoordinated in a distorted linear configuration by two 1-(2-hydroxy-ethyl)-2-methyl-5-nitro-imidazole 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 inter-actions, while two weak intra-molecular C-H⋯O inter-actions 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

[Ag(C6H9N3O3)2]NO3

M = 512.2

Triclinic,

a = 6.6912 (1) Å

b = 11.6846 (3) Å

c = 12.9052 (3) Å

α = 63.707 (1)°

β = 88.820 (1)°

γ = 87.486 (1)°

V = 903.72 (3) Å3

Z = 2

Mo Kα radiation

μ = 1.18 mm−1

T = 100.0 (1) K

0.74 × 0.22 × 0.1 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.476, T max = 0.892

20384 measured reflections

6509 independent reflections

5958 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.059

S = 1.08

6509 reflections

291 parameters

H-atom parameters constrained

Δρmax = 0.58 e Å−3

Δρmin = −0.65 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: 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 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808009860/ez2123sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808009860/ez2123Isup2.hkl

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

[Ag(C6H9N3O3)2]NO3	Z = 2
Mr = 512.2	F000 = 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 = 3.2–37.8º
c = 12.9052 (3) Å	µ = 1.18 mm−1
α = 63.707 (1)º	T = 100.0 (1) K
β = 88.820 (1)º	Plate, colourless
γ = 87.486 (1)º	0.74 × 0.22 × 0.1 mm
V = 903.72 (3) Å3

Bruker SMART APEXII CCD area-detector diffractometer	Rint = 0.026
φ and ω scans	θmax = 32.5º
Absorption correction: multi-scan(SADABS; Bruker, 2005)	θmin = 2.0º
Tmin = 0.476, Tmax = 0.892	h = −10→10
20384 measured reflections	k = −17→17
6509 independent reflections	l = −19→19
5958 reflections with I > 2σ(I)

Refinement on F2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.0281P)2 + 0.2414P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.024	(Δ/σ)max = 0.005
wR(F2) = 0.059	Δρmax = 0.58 e Å−3
S = 1.08	Δρmin = −0.65 e Å−3
6509 reflections	Extinction correction: none
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

Table 1

Hydrogen-bond geometry (Å, °)

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) ; (ii) .