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In the crystal structure of the title complex, [Ag(C
12H
8N
4O)(NO
3)]
n, each silver(I) center is coordinated by two N atoms of the pyridine rings of the bridging ligand 2,5-bis(4-pyridyl)-1,3,4-oxadiazole and one oxygen donor of the nitrate anion, giving a trigonal coordination geometry. The ligands bridge the silver(I) centers to form a one-dimensional linear structure, which is further linked into a double-chain motif through intermolecular C—H

O hydrogen bonds.
Supporting information
CCDC reference: 204655
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean
(C-C) = 0.006 Å
- R factor = 0.040
- wR factor = 0.117
- Data-to-parameter ratio = 11.6
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level C:
PLAT_737 Alert C D...A Calc 3.271(7), Rep 3.270(3) .... 2.33 su-Ratio
C9 -O12 1.555 2.776
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
A CH3CN solution of AgNO3 (42.5 mg, 0.25 mmol) was carefully layered onto a CHCl3 solution of the ligand 2,5-bis(4-pyridyl)-1,3,4-oxadiazole (56.0 mg, 0.25 mmol). Colorless block-shaped single crystals of (I) suitable for X-ray diffraction were obtained after ca two weeks at room temperature. Yield: 75%. Analysis calculated for the title complex: C 36.57, H 2.05, N 17.77%; found: C 36.48, H 2.06, N 17.82%. FT—IR data (KBr pellet, cm−1): 3178 (w), 3096 (m), 3049 (m), 2934 (w), 2430 (m), 2332 (m), 1993 (w), 1971 (w), 1876 (w), 1747 (m), 1612 (s), 1564 (s), 1540 (s), 1485 (s), 1427 (s), 1402 (s), 1356 (s), 1336 (s), 1302 (s), 1215 (s), 1121 (m), 1097 (m), 1061 (m), 1039 (m), 1012 (s), 970 (m), 892 (w), 846 (s), 823 (m), 747 (m), 727 (s), 713 (s), 699 (m).
H atoms were placed in the geometrically calculated positions and included in the final refinement in the riding-model approximation, with displacement parameters derived from the atoms to which they were bonded.
Data collection: SMART (BRUKER, 1998); cell refinement: SMART (BRUKER, 1998); data reduction: SAINT (BRUKER, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Bruker, 1998)
catena-Poly[silver(I)-2,5-bis(4-pyridyl)-1,3,4-oxadiazole nitrate]
top
Crystal data top
[Ag(C12H8N4O)(NO3] | Z = 2 |
Mr = 394.10 | F(000) = 388 |
Triclinic, P1 | Dx = 1.986 Mg m−3 |
a = 8.3649 (11) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.9480 (13) Å | Cell parameters from 2737 reflections |
c = 9.8344 (14) Å | θ = 2.5–25.0° |
α = 74.713 (2)° | µ = 1.56 mm−1 |
β = 77.828 (3)° | T = 298 K |
γ = 69.389 (3)° | Block, colorless |
V = 658.90 (16) Å3 | 0.15 × 0.15 × 0.15 mm |
Data collection top
Bruker SMART 1000 diffractometer | 2016 reflections with I > 2σ(I) |
ω scans | Rint = 0.021 |
Absorption correction: multi-scan [SAINT (Bruker 1998) and SADABS (Sheldrick, 1997)] | θmax = 25.0° |
Tmin = 0.491, Tmax = 0.792 | h = −6→9 |
2737 measured reflections | k = −7→10 |
2303 independent reflections | l = −11→11 |
Refinement top
Refinement on F2 | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.040 | w = 1/[σ2(Fo2) + (0.087P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.117 | (Δ/σ)max = 0.001 |
S = 1.06 | Δρmax = 0.81 e Å−3 |
2303 reflections | Δρmin = −0.73 e Å−3 |
199 parameters | |
Crystal data top
[Ag(C12H8N4O)(NO3] | γ = 69.389 (3)° |
Mr = 394.10 | V = 658.90 (16) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.3649 (11) Å | Mo Kα radiation |
b = 8.9480 (13) Å | µ = 1.56 mm−1 |
c = 9.8344 (14) Å | T = 298 K |
α = 74.713 (2)° | 0.15 × 0.15 × 0.15 mm |
β = 77.828 (3)° | |
Data collection top
Bruker SMART 1000 diffractometer | 2303 independent reflections |
Absorption correction: multi-scan [SAINT (Bruker 1998) and SADABS (Sheldrick, 1997)] | 2016 reflections with I > 2σ(I) |
Tmin = 0.491, Tmax = 0.792 | Rint = 0.021 |
2737 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.040 | 199 parameters |
wR(F2) = 0.117 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.81 e Å−3 |
2303 reflections | Δρmin = −0.73 e Å−3 |
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. Full-MATRIX |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Ag1 | 1.08174 (4) | 0.79990 (4) | 0.95985 (3) | 0.0569 (2) | |
O1 | 0.4770 (3) | 0.7225 (3) | 0.5734 (3) | 0.0376 (6) | |
N1 | 0.8793 (4) | 0.7625 (4) | 0.8714 (3) | 0.0457 (8) | |
N2 | 0.3830 (5) | 0.6032 (4) | 0.7866 (4) | 0.0448 (8) | |
N3 | 0.2890 (4) | 0.5953 (4) | 0.6876 (3) | 0.0432 (7) | |
N4 | 0.1864 (4) | 0.7403 (4) | 0.1672 (4) | 0.0424 (7) | |
C1 | 0.8614 (5) | 0.8098 (5) | 0.7311 (4) | 0.0444 (9) | |
H1A | 0.9386 | 0.8582 | 0.6696 | 0.053* | |
C2 | 0.7353 (5) | 0.7897 (5) | 0.6761 (4) | 0.0391 (8) | |
H2A | 0.7255 | 0.8261 | 0.5796 | 0.047* | |
C3 | 0.6219 (5) | 0.7143 (4) | 0.7666 (4) | 0.0362 (8) | |
C4 | 0.6394 (6) | 0.6652 (5) | 0.9100 (4) | 0.0459 (9) | |
H4A | 0.5654 | 0.6144 | 0.9736 | 0.055* | |
C5 | 0.7689 (6) | 0.6931 (6) | 0.9563 (4) | 0.0501 (10) | |
H5A | 0.7790 | 0.6612 | 1.0529 | 0.060* | |
C6 | 0.4906 (5) | 0.6787 (5) | 0.7149 (4) | 0.0380 (8) | |
C7 | 0.3489 (5) | 0.6659 (4) | 0.5659 (4) | 0.0360 (8) | |
C8 | 0.2947 (5) | 0.6915 (4) | 0.4278 (4) | 0.0363 (8) | |
C9 | 0.3639 (5) | 0.7798 (5) | 0.3066 (4) | 0.0413 (9) | |
H9A | 0.4484 | 0.8230 | 0.3107 | 0.050* | |
C10 | 0.3054 (5) | 0.8023 (5) | 0.1806 (4) | 0.0431 (9) | |
H10A | 0.3506 | 0.8637 | 0.0999 | 0.052* | |
C11 | 0.1230 (5) | 0.6531 (5) | 0.2829 (4) | 0.0454 (9) | |
H11A | 0.0420 | 0.6077 | 0.2747 | 0.054* | |
C12 | 0.1720 (5) | 0.6262 (5) | 0.4156 (4) | 0.0445 (9) | |
H12A | 0.1235 | 0.5656 | 0.4949 | 0.053* | |
N11 | 1.2250 (4) | 1.0537 (4) | 0.7428 (4) | 0.0489 (8) | |
O11 | 1.2338 (6) | 1.0113 (5) | 0.8723 (4) | 0.0788 (11) | |
O12 | 1.2765 (6) | 1.1659 (6) | 0.6709 (4) | 0.0891 (13) | |
O13 | 1.1575 (5) | 0.9844 (4) | 0.6877 (5) | 0.0754 (10) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ag1 | 0.0655 (3) | 0.0801 (3) | 0.0394 (3) | −0.0343 (2) | −0.02544 (17) | −0.00568 (17) |
O1 | 0.0391 (13) | 0.0523 (15) | 0.0262 (13) | −0.0175 (11) | −0.0123 (10) | −0.0054 (11) |
N1 | 0.0491 (18) | 0.066 (2) | 0.0307 (17) | −0.0221 (16) | −0.0161 (14) | −0.0095 (15) |
N2 | 0.0519 (19) | 0.0573 (19) | 0.0329 (17) | −0.0252 (16) | −0.0132 (15) | −0.0049 (15) |
N3 | 0.0508 (18) | 0.0544 (18) | 0.0316 (17) | −0.0246 (15) | −0.0129 (14) | −0.0038 (14) |
N4 | 0.0433 (17) | 0.0515 (18) | 0.0353 (17) | −0.0106 (14) | −0.0175 (14) | −0.0096 (14) |
C1 | 0.047 (2) | 0.056 (2) | 0.033 (2) | −0.0199 (18) | −0.0117 (17) | −0.0050 (17) |
C2 | 0.048 (2) | 0.048 (2) | 0.0247 (17) | −0.0172 (17) | −0.0138 (15) | −0.0033 (15) |
C3 | 0.0374 (18) | 0.0419 (18) | 0.0328 (18) | −0.0114 (15) | −0.0125 (15) | −0.0086 (15) |
C4 | 0.053 (2) | 0.064 (2) | 0.0276 (19) | −0.027 (2) | −0.0102 (16) | −0.0034 (17) |
C5 | 0.058 (2) | 0.072 (3) | 0.0289 (19) | −0.028 (2) | −0.0164 (18) | −0.0065 (18) |
C6 | 0.0405 (19) | 0.046 (2) | 0.0269 (18) | −0.0102 (16) | −0.0100 (15) | −0.0064 (15) |
C7 | 0.0352 (18) | 0.0414 (19) | 0.0327 (19) | −0.0086 (15) | −0.0123 (15) | −0.0083 (15) |
C8 | 0.0360 (18) | 0.0419 (19) | 0.0317 (19) | −0.0085 (15) | −0.0119 (15) | −0.0080 (15) |
C9 | 0.045 (2) | 0.049 (2) | 0.036 (2) | −0.0202 (17) | −0.0152 (17) | −0.0047 (16) |
C10 | 0.047 (2) | 0.051 (2) | 0.034 (2) | −0.0175 (17) | −0.0141 (17) | −0.0032 (16) |
C11 | 0.042 (2) | 0.060 (2) | 0.041 (2) | −0.0194 (18) | −0.0155 (17) | −0.0102 (18) |
C12 | 0.049 (2) | 0.059 (2) | 0.0328 (19) | −0.0260 (18) | −0.0116 (16) | −0.0046 (16) |
N11 | 0.0431 (18) | 0.063 (2) | 0.041 (2) | −0.0186 (16) | −0.0064 (15) | −0.0074 (16) |
O11 | 0.096 (3) | 0.096 (3) | 0.0357 (18) | −0.025 (2) | −0.0187 (18) | 0.0009 (17) |
O12 | 0.090 (3) | 0.128 (3) | 0.066 (2) | −0.076 (3) | −0.021 (2) | 0.018 (2) |
O13 | 0.076 (2) | 0.073 (2) | 0.092 (3) | −0.0243 (19) | −0.021 (2) | −0.032 (2) |
Geometric parameters (Å, º) top
Ag1—N1 | 2.216 (3) | C3—C4 | 1.385 (5) |
Ag1—N4i | 2.250 (3) | C3—C6 | 1.460 (5) |
Ag1—O11 | 2.512 (5) | C4—C5 | 1.380 (6) |
O1—C7 | 1.358 (5) | C4—H4A | 0.9300 |
O1—C6 | 1.361 (4) | C5—H5A | 0.9300 |
N1—C5 | 1.319 (5) | C7—C8 | 1.458 (5) |
N1—C1 | 1.356 (5) | C8—C9 | 1.384 (5) |
N2—C6 | 1.294 (5) | C8—C12 | 1.386 (5) |
N2—N3 | 1.404 (5) | C9—C10 | 1.368 (6) |
N3—C7 | 1.286 (5) | C9—H9A | 0.9300 |
N4—C11 | 1.324 (5) | C10—H10A | 0.9300 |
N4—C10 | 1.341 (5) | C11—C12 | 1.385 (6) |
N4—Ag1ii | 2.250 (3) | C11—H11A | 0.9300 |
C1—C2 | 1.365 (6) | C12—H12A | 0.9300 |
C1—H1A | 0.9300 | N11—O12 | 1.223 (5) |
C2—C3 | 1.388 (5) | N11—O11 | 1.239 (5) |
C2—H2A | 0.9300 | N11—O13 | 1.245 (5) |
| | | |
N1—Ag1—N4i | 139.84 (13) | C4—C5—H5A | 118.1 |
N1—Ag1—O11 | 130.27 (12) | N2—C6—O1 | 112.5 (3) |
N4i—Ag1—O11 | 87.79 (12) | N2—C6—C3 | 128.3 (3) |
C7—O1—C6 | 102.3 (3) | O1—C6—C3 | 119.1 (3) |
C5—N1—C1 | 117.3 (4) | N3—C7—O1 | 113.2 (3) |
C5—N1—Ag1 | 120.0 (3) | N3—C7—C8 | 128.0 (3) |
C1—N1—Ag1 | 122.7 (3) | O1—C7—C8 | 118.9 (3) |
C6—N2—N3 | 106.2 (3) | C9—C8—C12 | 118.5 (3) |
C7—N3—N2 | 105.9 (3) | C9—C8—C7 | 121.4 (3) |
C11—N4—C10 | 117.7 (4) | C12—C8—C7 | 120.1 (3) |
C11—N4—Ag1ii | 121.0 (3) | C10—C9—C8 | 118.7 (4) |
C10—N4—Ag1ii | 121.1 (3) | C10—C9—H9A | 120.7 |
N1—C1—C2 | 123.0 (4) | C8—C9—H9A | 120.7 |
N1—C1—H1A | 118.5 | N4—C10—C9 | 123.4 (4) |
C2—C1—H1A | 118.5 | N4—C10—H10A | 118.3 |
C1—C2—C3 | 118.9 (3) | C9—C10—H10A | 118.3 |
C1—C2—H2A | 120.5 | N4—C11—C12 | 123.0 (4) |
C3—C2—H2A | 120.5 | N4—C11—H11A | 118.5 |
C4—C3—C2 | 118.4 (3) | C12—C11—H11A | 118.5 |
C4—C3—C6 | 119.2 (3) | C11—C12—C8 | 118.6 (4) |
C2—C3—C6 | 122.3 (3) | C11—C12—H12A | 120.7 |
C5—C4—C3 | 118.6 (4) | C8—C12—H12A | 120.7 |
C5—C4—H4A | 120.7 | O12—N11—O11 | 120.4 (4) |
C3—C4—H4A | 120.7 | O12—N11—O13 | 120.3 (4) |
N1—C5—C4 | 123.7 (4) | O11—N11—O13 | 119.2 (4) |
N1—C5—H5A | 118.1 | N11—O11—Ag1 | 104.7 (3) |
Symmetry codes: (i) x+1, y, z+1; (ii) x−1, y, z−1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2A···O12iii | 0.93 | 2.45 | 3.350 (4) | 163 |
C9—H9A···O12iii | 0.93 | 2.38 | 3.270 (3) | 160 |
Symmetry code: (iii) −x+2, −y+2, −z+1. |
Experimental details
Crystal data |
Chemical formula | [Ag(C12H8N4O)(NO3] |
Mr | 394.10 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 298 |
a, b, c (Å) | 8.3649 (11), 8.9480 (13), 9.8344 (14) |
α, β, γ (°) | 74.713 (2), 77.828 (3), 69.389 (3) |
V (Å3) | 658.90 (16) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.56 |
Crystal size (mm) | 0.15 × 0.15 × 0.15 |
|
Data collection |
Diffractometer | Bruker SMART 1000 diffractometer |
Absorption correction | Multi-scan [SAINT (Bruker 1998) and SADABS (Sheldrick, 1997)] |
Tmin, Tmax | 0.491, 0.792 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2737, 2303, 2016 |
Rint | 0.021 |
(sin θ/λ)max (Å−1) | 0.595 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.117, 1.06 |
No. of reflections | 2303 |
No. of parameters | 199 |
No. of restraints | ? |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.81, −0.73 |
Selected geometric parameters (Å, º) topAg1—N1 | 2.216 (3) | Ag1—O11 | 2.512 (5) |
Ag1—N4i | 2.250 (3) | | |
| | | |
N1—Ag1—N4i | 139.84 (13) | N4i—Ag1—O11 | 87.79 (12) |
N1—Ag1—O11 | 130.27 (12) | | |
Symmetry code: (i) x+1, y, z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2A···O12ii | .93 | 2.45 | 3.350 (4) | 163 |
C9—H9A···O12ii | .93 | 2.38 | 3.270 (3) | 160 |
Symmetry code: (ii) −x+2, −y+2, −z+1. |

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Great efforts have been devoted to metal-directed coordination supramolecules due to their interesting topological structures and potential applications as functional materials (Batten & Robson, 1998; Eddaoudi et al., 2001). Using a `building block' methodology, combination of linear 4,4'-bipyridine-based ligands and metal ions has generated a wide variety of solid-state architectures (Hagrman et al., 1999). Recently, an interesting angular dipyridyl ligand, 2,5-bis(4-pyridyl)-1,3,4-oxadiazole, which could potentially provide both discrete and divergent topologies upon metal complexation under appropriate conditions (Du, Bu et al., 2002; Du, Chen et al., 2002; Du, Liu et al., 2002) has been developed. Here, we report on the crystal structure of a silver(I) complex of this ligand, which reveals that it is a neutral one-dimensional coordination polymer, (I).
As depicted in Fig. 1, the AgI center coordinates to two N atoms of the pyridine rings from the bridging ligand, and one O atom of the nitrate anion. The coordination environment of each AgI ion can best be described as trigonal, with the AgI ion deviating from the mean coordination plane by ca 0.18 Å. The mean atomic displacement from the least-squares plane of the ligand is equal to 0.0733 Å. The two pyridine rings in the same ligand molecule are inclined by 4.9 and 4.7°, with respect to the central oxadiazole plane, and by 8.5° with respect to one another.
As shown in Fig. 2, within this 1:1 ligand–metal polymeric chain, the neighboring Ag···Ag separation is 14.191 Å, and the nearest Ag···Ag distance between the coordination chains is only 3.592 Å. This is slightly longer than the van der Waals contact distance for Ag···Ag (3.40 Å), illustrating the lack of direct metal—metal interaction (Hartshorn & Steel, 1998). Of further interest is the fact that each nitrate anion in the chain acts as an acceptor of two intermolecular C—H···O hydrogen bonds (with the pyridine rings of the adjacent coordination chain), forming a unique double-chain supramolecular motif (Fig. 2). The C···O and H···O separations, and the bond angles are listed in Table 2, which are in the normal range for weak hydrogen bonding interactions.