Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807052129/hy2089sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807052129/hy2089Isup2.hkl |
CCDC reference: 603382
A solution of AgNO3 (0.104 g, 0.61 mmol), 2-(3-pyridyl)benzimidazole (Alcade et al., 1992) (0.14 g, 0.61 mmol) and H2O (15 ml) was stirred under ambient condition. The mixture was sealed in a 25 ml Teflon-lined stainless steel vessel, heated at 383 K for 3 d and then cooled to room temperature. The resulting product was collected by filtration, washed with distilled water and dried in air (yield 80%).
H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 and N—H = 0.86Å and Uiso(H) = 1.2Ueq(C,N).
The 2-(3-pyridyl)benzimidazole ligand acts as terminal (Chen et al., 2005) or bidentate ligand (Su et al., 1999) in metal complexes. Herein we report the synthesis and structure of a binuclear silver(I) complex with 2-(3-pyridyl)benzimidazole.
In the title compound, the centrosymmetric binuclear cyclic complex contains two AgI atoms bridged by two 2-(3-pyridyl)benzimidazole ligands via pyridyl and imidazole N atoms in a head-to-end mode (Fig. 1). The AgI atom is in an approximate linear coordination geometry. The nitrate anion acts as a counter ion and is weakly coordinated to AgI atoms [Ag1···O1 = 2.686 (13) Å, Ag1···O3 = 2.847 (7)Å and Ag1···O2i = 2.782 (5) Å; symmetry code: (i) 1 - x, 2 - y, 2 - z]. The Ag1···O1 and Ag1···O3 interactions as well as N3—H···O1 hydrogen bonds connect the binuclear units into a one-dimensional chain (Fig. 2). Crystal packing is stabilized by the Ag1···O2i interactions and offset π–π interactions between the chains (Fig. 3).
For related literature, see: Alcade et al. (1992); Chen et al. (2005); Su et al. (1999).
Data collection: CrystalClear (Rigaku, 2000); cell refinement: CrystalClear (Rigaku, 2000); data reduction: CrystalClear (Rigaku, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1994); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
[Ag2(C12H9N3)2](NO3)2 | Z = 1 |
Mr = 730.20 | F(000) = 360 |
Triclinic, P1 | Dx = 1.962 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.317 (3) Å | Cell parameters from 1908 reflections |
b = 9.097 (4) Å | θ = 2.7–27.5° |
c = 9.934 (4) Å | µ = 1.64 mm−1 |
α = 105.949 (18)° | T = 293 K |
β = 96.797 (15)° | Prism, colorless |
γ = 116.892 (11)° | 0.50 × 0.45 × 0.40 mm |
V = 618.2 (5) Å3 |
Rigaku Mercury CCD diffractometer | 2758 independent reflections |
Radiation source: fine-focus sealed tube | 2586 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.013 |
ω scans | θmax = 27.5°, θmin = 2.7° |
Absorption correction: multi-scan (CrystalClear; Rigaku, 2000) | h = −10→6 |
Tmin = 0.444, Tmax = 0.528 | k = −10→11 |
4673 measured reflections | l = −12→12 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.024 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.063 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0396P)2 + 0.1553P] where P = (Fo2 + 2Fc2)/3 |
2758 reflections | (Δ/σ)max = 0.002 |
181 parameters | Δρmax = 0.59 e Å−3 |
0 restraints | Δρmin = −0.63 e Å−3 |
[Ag2(C12H9N3)2](NO3)2 | γ = 116.892 (11)° |
Mr = 730.20 | V = 618.2 (5) Å3 |
Triclinic, P1 | Z = 1 |
a = 8.317 (3) Å | Mo Kα radiation |
b = 9.097 (4) Å | µ = 1.64 mm−1 |
c = 9.934 (4) Å | T = 293 K |
α = 105.949 (18)° | 0.50 × 0.45 × 0.40 mm |
β = 96.797 (15)° |
Rigaku Mercury CCD diffractometer | 2758 independent reflections |
Absorption correction: multi-scan (CrystalClear; Rigaku, 2000) | 2586 reflections with I > 2σ(I) |
Tmin = 0.444, Tmax = 0.528 | Rint = 0.013 |
4673 measured reflections |
R[F2 > 2σ(F2)] = 0.024 | 0 restraints |
wR(F2) = 0.063 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.59 e Å−3 |
2758 reflections | Δρmin = −0.63 e Å−3 |
181 parameters |
x | y | z | Uiso*/Ueq | ||
Ag1 | 0.69487 (2) | 0.909984 (19) | 0.836791 (18) | 0.03879 (8) | |
C1 | 1.0525 (3) | 0.7222 (3) | 1.1866 (2) | 0.0340 (4) | |
H1A | 1.1496 | 0.7688 | 1.2706 | 0.041* | |
C2 | 0.8990 (3) | 0.5561 (3) | 1.1521 (2) | 0.0349 (4) | |
H2A | 0.8944 | 0.4912 | 1.2108 | 0.042* | |
C3 | 0.7521 (3) | 0.4871 (3) | 1.0294 (2) | 0.0315 (4) | |
H3A | 0.6471 | 0.3754 | 1.0046 | 0.038* | |
C4 | 0.7635 (3) | 0.5871 (3) | 0.9437 (2) | 0.0275 (4) | |
C5 | 0.9260 (3) | 0.7512 (3) | 0.9839 (2) | 0.0299 (4) | |
H5A | 0.9368 | 0.8166 | 0.9246 | 0.036* | |
C6 | 0.6097 (3) | 0.5236 (2) | 0.8146 (2) | 0.0278 (4) | |
C7 | 0.4068 (3) | 0.5075 (3) | 0.6448 (2) | 0.0296 (4) | |
C8 | 0.2976 (3) | 0.5400 (3) | 0.5523 (2) | 0.0377 (5) | |
H8A | 0.3261 | 0.6549 | 0.5640 | 0.045* | |
C9 | 0.1461 (3) | 0.3949 (4) | 0.4431 (3) | 0.0452 (5) | |
H9A | 0.0698 | 0.4125 | 0.3809 | 0.054* | |
C10 | 0.1036 (3) | 0.2212 (4) | 0.4230 (3) | 0.0485 (6) | |
H10A | 0.0002 | 0.1266 | 0.3476 | 0.058* | |
C11 | 0.2107 (3) | 0.1873 (3) | 0.5119 (3) | 0.0420 (5) | |
H11A | 0.1839 | 0.0722 | 0.4977 | 0.050* | |
C12 | 0.3621 (3) | 0.3342 (3) | 0.6251 (2) | 0.0320 (4) | |
N1 | 1.0673 (2) | 0.8195 (2) | 1.10372 (19) | 0.0310 (3) | |
N2 | 0.5635 (2) | 0.6242 (2) | 0.76462 (17) | 0.0285 (3) | |
N3 | 0.4925 (2) | 0.3486 (2) | 0.73404 (19) | 0.0323 (4) | |
H3B | 0.4988 | 0.2622 | 0.7486 | 0.039* | |
N4 | 0.3636 (3) | 0.9842 (2) | 0.83250 (19) | 0.0333 (4) | |
O1 | 0.4791 (3) | 1.0384 (3) | 0.7610 (2) | 0.0500 (4) | |
O2 | 0.2846 (3) | 1.0683 (3) | 0.8762 (2) | 0.0503 (4) | |
O3 | 0.3345 (3) | 0.8520 (3) | 0.8593 (2) | 0.0623 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ag1 | 0.03312 (11) | 0.02520 (10) | 0.05195 (12) | 0.01146 (8) | 0.00234 (8) | 0.01578 (8) |
C1 | 0.0334 (11) | 0.0342 (11) | 0.0355 (10) | 0.0180 (9) | 0.0048 (8) | 0.0151 (8) |
C2 | 0.0369 (11) | 0.0375 (11) | 0.0399 (10) | 0.0203 (10) | 0.0140 (9) | 0.0240 (9) |
C3 | 0.0300 (10) | 0.0273 (10) | 0.0393 (10) | 0.0130 (8) | 0.0126 (8) | 0.0168 (8) |
C4 | 0.0267 (9) | 0.0252 (9) | 0.0341 (9) | 0.0148 (8) | 0.0094 (8) | 0.0128 (7) |
C5 | 0.0273 (10) | 0.0250 (9) | 0.0389 (10) | 0.0131 (8) | 0.0064 (8) | 0.0155 (8) |
C6 | 0.0233 (9) | 0.0231 (9) | 0.0351 (9) | 0.0087 (7) | 0.0080 (7) | 0.0137 (7) |
C7 | 0.0245 (9) | 0.0311 (10) | 0.0333 (9) | 0.0127 (8) | 0.0092 (8) | 0.0139 (8) |
C8 | 0.0395 (12) | 0.0449 (12) | 0.0377 (10) | 0.0259 (11) | 0.0113 (9) | 0.0197 (9) |
C9 | 0.0361 (12) | 0.0635 (16) | 0.0377 (11) | 0.0267 (12) | 0.0061 (9) | 0.0207 (11) |
C10 | 0.0313 (12) | 0.0538 (15) | 0.0387 (11) | 0.0104 (11) | 0.0001 (9) | 0.0109 (11) |
C11 | 0.0337 (12) | 0.0330 (11) | 0.0432 (12) | 0.0073 (10) | 0.0050 (9) | 0.0113 (9) |
C12 | 0.0251 (9) | 0.0311 (10) | 0.0347 (10) | 0.0097 (8) | 0.0068 (8) | 0.0140 (8) |
N1 | 0.0268 (8) | 0.0253 (8) | 0.0401 (9) | 0.0130 (7) | 0.0047 (7) | 0.0134 (7) |
N2 | 0.0265 (8) | 0.0256 (8) | 0.0342 (8) | 0.0132 (7) | 0.0074 (7) | 0.0128 (6) |
N3 | 0.0287 (9) | 0.0229 (8) | 0.0400 (9) | 0.0092 (7) | 0.0039 (7) | 0.0135 (7) |
N4 | 0.0293 (9) | 0.0276 (9) | 0.0381 (9) | 0.0129 (7) | 0.0011 (7) | 0.0117 (7) |
O1 | 0.0481 (10) | 0.0499 (10) | 0.0734 (12) | 0.0307 (9) | 0.0297 (9) | 0.0373 (9) |
O2 | 0.0553 (11) | 0.0530 (11) | 0.0576 (10) | 0.0381 (10) | 0.0188 (9) | 0.0214 (9) |
O3 | 0.0801 (15) | 0.0443 (10) | 0.0842 (14) | 0.0360 (11) | 0.0334 (12) | 0.0418 (10) |
Ag1—N2 | 2.1650 (19) | C7—C8 | 1.396 (3) |
Ag1—N1i | 2.1994 (19) | C8—C9 | 1.375 (3) |
C1—N1 | 1.343 (3) | C8—H8A | 0.9300 |
C1—C2 | 1.377 (3) | C9—C10 | 1.403 (4) |
C1—H1A | 0.9300 | C9—H9A | 0.9300 |
C2—C3 | 1.381 (3) | C10—C11 | 1.371 (4) |
C2—H2A | 0.9300 | C10—H10A | 0.9300 |
C3—C4 | 1.389 (3) | C11—C12 | 1.397 (3) |
C3—H3A | 0.9300 | C11—H11A | 0.9300 |
C4—C5 | 1.391 (3) | C12—N3 | 1.372 (3) |
C4—C6 | 1.467 (3) | N1—Ag1i | 2.1994 (19) |
C5—N1 | 1.336 (3) | N3—O1ii | 2.860 (3) |
C5—H5A | 0.9300 | N3—H3B | 0.8600 |
C6—N2 | 1.324 (2) | N4—O3 | 1.226 (3) |
C6—N3 | 1.355 (3) | N4—O2 | 1.243 (2) |
C7—N2 | 1.389 (3) | N4—O1 | 1.263 (3) |
C7—C12 | 1.395 (3) | ||
N2—Ag1—N1i | 154.25 (7) | C8—C9—H9A | 119.1 |
N1—C1—C2 | 122.6 (2) | C10—C9—H9A | 119.1 |
N1—C1—H1A | 118.7 | C11—C10—C9 | 121.6 (2) |
C2—C1—H1A | 118.7 | C11—C10—H10A | 119.2 |
C1—C2—C3 | 119.25 (19) | C9—C10—H10A | 119.2 |
C1—C2—H2A | 120.4 | C10—C11—C12 | 116.6 (2) |
C3—C2—H2A | 120.4 | C10—C11—H11A | 121.7 |
C2—C3—C4 | 119.00 (19) | C12—C11—H11A | 121.7 |
C2—C3—H3A | 120.5 | N3—C12—C7 | 105.85 (18) |
C4—C3—H3A | 120.5 | N3—C12—C11 | 132.0 (2) |
C3—C4—C5 | 118.03 (19) | C7—C12—C11 | 122.1 (2) |
C3—C4—C6 | 121.62 (18) | C5—N1—C1 | 118.00 (18) |
C5—C4—C6 | 120.35 (17) | C5—N1—Ag1i | 119.02 (13) |
N1—C5—C4 | 123.10 (18) | C1—N1—Ag1i | 122.89 (14) |
N1—C5—H5A | 118.4 | C6—N2—C7 | 105.76 (16) |
C4—C5—H5A | 118.4 | C6—N2—Ag1 | 130.80 (14) |
N2—C6—N3 | 111.85 (18) | C7—N2—Ag1 | 123.40 (13) |
N2—C6—C4 | 125.91 (18) | C6—N3—C12 | 107.64 (17) |
N3—C6—C4 | 122.21 (18) | C6—N3—O1ii | 131.71 (14) |
N2—C7—C12 | 108.90 (17) | C12—N3—O1ii | 120.65 (14) |
N2—C7—C8 | 130.6 (2) | C6—N3—H3B | 126.2 |
C12—C7—C8 | 120.5 (2) | C12—N3—H3B | 126.2 |
C9—C8—C7 | 117.2 (2) | O3—N4—O2 | 121.6 (2) |
C9—C8—H8A | 121.4 | O3—N4—O1 | 119.38 (19) |
C7—C8—H8A | 121.4 | O2—N4—O1 | 119.00 (19) |
C8—C9—C10 | 121.9 (2) | ||
N1—C1—C2—C3 | −1.4 (3) | C4—C5—N1—Ag1i | −174.98 (14) |
C1—C2—C3—C4 | 0.3 (3) | C2—C1—N1—C5 | 0.5 (3) |
C2—C3—C4—C5 | 1.6 (3) | C2—C1—N1—Ag1i | 176.94 (16) |
C2—C3—C4—C6 | −178.09 (18) | N3—C6—N2—C7 | 0.1 (2) |
C3—C4—C5—N1 | −2.7 (3) | C4—C6—N2—C7 | −177.85 (18) |
C6—C4—C5—N1 | 177.04 (18) | N3—C6—N2—Ag1 | −177.81 (12) |
C3—C4—C6—N2 | 148.1 (2) | C4—C6—N2—Ag1 | 4.2 (3) |
C5—C4—C6—N2 | −31.7 (3) | C12—C7—N2—C6 | −0.2 (2) |
C3—C4—C6—N3 | −29.7 (3) | C8—C7—N2—C6 | 178.7 (2) |
C5—C4—C6—N3 | 150.54 (19) | C12—C7—N2—Ag1 | 177.91 (13) |
N2—C7—C8—C9 | −178.6 (2) | C8—C7—N2—Ag1 | −3.2 (3) |
C12—C7—C8—C9 | 0.2 (3) | N1i—Ag1—N2—C6 | 52.9 (2) |
C7—C8—C9—C10 | −1.0 (3) | N1i—Ag1—N2—C7 | −124.70 (17) |
C8—C9—C10—C11 | 0.3 (4) | N2—C6—N3—C12 | 0.0 (2) |
C9—C10—C11—C12 | 1.1 (4) | C4—C6—N3—C12 | 178.08 (17) |
N2—C7—C12—N3 | 0.2 (2) | N2—C6—N3—O1ii | −178.99 (13) |
C8—C7—C12—N3 | −178.82 (18) | C4—C6—N3—O1ii | −0.9 (3) |
N2—C7—C12—C11 | −179.67 (19) | C7—C12—N3—C6 | −0.2 (2) |
C8—C7—C12—C11 | 1.3 (3) | C11—C12—N3—C6 | 179.7 (2) |
C10—C11—C12—N3 | 178.2 (2) | C7—C12—N3—O1ii | 178.99 (12) |
C10—C11—C12—C7 | −1.9 (3) | C11—C12—N3—O1ii | −1.1 (3) |
C4—C5—N1—C1 | 1.6 (3) |
Symmetry codes: (i) −x+2, −y+2, −z+2; (ii) x, y−1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3B···O1ii | 0.86 | 2.01 | 2.860 (3) | 172 |
Symmetry code: (ii) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | [Ag2(C12H9N3)2](NO3)2 |
Mr | 730.20 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 8.317 (3), 9.097 (4), 9.934 (4) |
α, β, γ (°) | 105.949 (18), 96.797 (15), 116.892 (11) |
V (Å3) | 618.2 (5) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 1.64 |
Crystal size (mm) | 0.50 × 0.45 × 0.40 |
Data collection | |
Diffractometer | Rigaku Mercury CCD |
Absorption correction | Multi-scan (CrystalClear; Rigaku, 2000) |
Tmin, Tmax | 0.444, 0.528 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4673, 2758, 2586 |
Rint | 0.013 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.024, 0.063, 1.04 |
No. of reflections | 2758 |
No. of parameters | 181 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.59, −0.63 |
Computer programs: CrystalClear (Rigaku, 2000), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Siemens, 1994).
Ag1—N2 | 2.1650 (19) | Ag1—N1i | 2.1994 (19) |
N2—Ag1—N1i | 154.25 (7) |
Symmetry code: (i) −x+2, −y+2, −z+2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3B···O1ii | 0.86 | 2.01 | 2.860 (3) | 172.0 |
Symmetry code: (ii) x, y−1, z. |
The 2-(3-pyridyl)benzimidazole ligand acts as terminal (Chen et al., 2005) or bidentate ligand (Su et al., 1999) in metal complexes. Herein we report the synthesis and structure of a binuclear silver(I) complex with 2-(3-pyridyl)benzimidazole.
In the title compound, the centrosymmetric binuclear cyclic complex contains two AgI atoms bridged by two 2-(3-pyridyl)benzimidazole ligands via pyridyl and imidazole N atoms in a head-to-end mode (Fig. 1). The AgI atom is in an approximate linear coordination geometry. The nitrate anion acts as a counter ion and is weakly coordinated to AgI atoms [Ag1···O1 = 2.686 (13) Å, Ag1···O3 = 2.847 (7)Å and Ag1···O2i = 2.782 (5) Å; symmetry code: (i) 1 - x, 2 - y, 2 - z]. The Ag1···O1 and Ag1···O3 interactions as well as N3—H···O1 hydrogen bonds connect the binuclear units into a one-dimensional chain (Fig. 2). Crystal packing is stabilized by the Ag1···O2i interactions and offset π–π interactions between the chains (Fig. 3).