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Acta Cryst. (2008). E64, m110    [ doi:10.1107/S1600536807064744 ]

catena-Poly[[silver(I)-[mu]-N-(3-pyridylmethyl)pyridine-4-carboxamide] nitrate monohydrate]

Y.-T. Ma and Q.-H. Zhao

Abstract top

In the title compound, {[Ag(C12H11N3O)]NO3·H2O}n, the Ag atom is coordinated by two N atoms from the heterocyclic ligand, giving a linear polycationic chain. Two long Ag...Onitrate interactions [2.667 (3) and 2.840 (3) Å] result in a three-dimensional network. The water molecule consolidates the network structure by forming hydrogen bonds, one to the polycationic chain and one to the nitrate anion.

Comment top

The reactions of silver(I) salts with flexible pyridyl type ligands have received considerable attention (Cordes et al., 2007; Kumar et al., 2006; Tong et al., 2002). Here, we report a new silver(I) complex (Fig. 1), which was prepared by the reaction of N-(3-pyridinylmethyl)-4-pyridine-carboxamide acting as a bidentate bridge ligand with AgNO3. In the cation, the Ag(I) atom is in a linear coordination environment and the Ag1—N1A and Ag1—N3 bond length are 2.152 (3) and 2.157 (3) Å, respectively. The N3—Ag1—N1i (i = -1 + x, 0.5 - y, 1/2 + z) bond angle is 172.55 (15) °, indicating that the N–Ag–N skeleton that gives rise to a chain structure is distorted by the presence of two Ag···Onitrate interactions. If these are regarded as formal bonds, the compound may be described as a three dimensional network structure (Fig. 2).

Related literature top

For related literature, see: Cordes & Hanton (2007); Kumar et al. (2006); Tong et al. (2002).

Experimental top

An aqueous solution (5 ml) of silver nitrate (1.0 mmol) was layered carefully over a methanol (5 ml) solution of N-(4-pyridylmethyl)-4-pyridinecarboxamide (1.0 mmol) in a tube, which was covered and kept away from light. Colorless crystals were obtained after two weeks. These were washed with methanol and collected in 50% yield. CHN elemental analysis: found C 35.86, H 3.55, N 13.79%; calc. for C12H13AgN4O5: C 35.93, H 3.27, N 13.96%.

Refinement top

All H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H distances of 0.93–0.97 Å, N—H distances of 0.86 Å and OW1—H distances of 0.85 Å, and with Uiso(H) = 1.2Ueq(C, N or O).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2003); cell refinement: CrystalClear (Rigaku/MSC, 2003); data reduction: CrystalClear (Rigaku/MSC, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 1999).

Figures top
[Figure 1] Fig. 1. The structure of the title complex, showing 30% probability displacement ellipsoids and the atom-numbering scheme. Symmetry-generated atoms in the plot are related by (-1 + x, 0.5 - y, 1/2 + z).
[Figure 2] Fig. 2. Crystal packing viewed down the c axis.
catena-Poly[[silver(I)-µ-N-(3-pyridylmethyl)pyridine-4-carboxamide] nitrate monohydrate] top
Crystal data top
[Ag(C12H11N3O)]NO3·H2OF000 = 800
Mr = 401.13Dx = 1.891 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5866 reflections
a = 12.177 (2) Åθ = 3.2–27.5º
b = 13.022 (3) ŵ = 1.46 mm−1
c = 8.9109 (18) ÅT = 293 (2) K
β = 94.21 (3)ºBlock, colorless
V = 1409.2 (5) Å30.6 × 0.4 × 0.2 mm
Z = 4
Data collection top
Rigaku Mercury CCD
diffractometer		3230 independent reflections
Radiation source: fine-focus sealed tube2399 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.065
T = 293(2) Kθmax = 27.5º
ω scansθmin = 3.1º
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2003)		h = −15→15
Tmin = 0.503, Tmax = 0.742k = −16→16
14304 measured reflectionsl = −11→11
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.101  w = 1/[σ2(Fo2) + (0.0433P)2 + 0.2355P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
3230 reflectionsΔρmax = 0.35 e Å−3
199 parametersΔρmin = −0.43 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Ag(C12H11N3O)]NO3·H2OV = 1409.2 (5) Å3
Mr = 401.13Z = 4
Monoclinic, P21/cMo Kα
a = 12.177 (2) ŵ = 1.46 mm−1
b = 13.022 (3) ÅT = 293 (2) K
c = 8.9109 (18) Å0.6 × 0.4 × 0.2 mm
β = 94.21 (3)º
Data collection top
Rigaku Mercury CCD
diffractometer		3230 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2003)		2399 reflections with I > 2σ(I)
Tmin = 0.503, Tmax = 0.742Rint = 0.065
14304 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.042199 parameters
wR(F2) = 0.101H-atom parameters constrained
S = 1.06Δρmax = 0.35 e Å−3
3230 reflectionsΔρmin = −0.43 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. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ag1−0.01568 (2)0.32484 (2)0.11987 (4)0.04917 (14)
N30.1306 (2)0.3030 (2)0.0011 (3)0.0377 (7)
C90.1867 (3)0.3832 (3)−0.0444 (4)0.0453 (9)
H9A0.16440.4486−0.01760.054*
C70.2524 (3)0.1954 (3)−0.1219 (4)0.0426 (9)
H7A0.27310.1291−0.14670.051*
C80.1637 (3)0.2107 (3)−0.0387 (4)0.0448 (9)
H8A0.12490.1537−0.00870.054*
C110.3109 (3)0.2785 (3)−0.1690 (4)0.0321 (7)
C100.2755 (3)0.3746 (3)−0.1283 (4)0.0418 (9)
H10A0.31200.4331−0.15800.050*
C120.4107 (3)0.2716 (3)−0.2571 (4)0.0348 (8)
N40.4370 (2)0.1789 (2)−0.3061 (3)0.0396 (7)
H4A0.39620.1273−0.28720.047*
C130.5327 (3)0.1630 (3)−0.3904 (4)0.0444 (9)
H13A0.54310.2231−0.45200.053*
H13B0.51880.1051−0.45760.053*
C40.6375 (3)0.1431 (3)−0.2938 (4)0.0335 (8)
C50.7368 (3)0.1578 (3)−0.3533 (4)0.0358 (8)
H5A0.73650.1849−0.44990.043*
N10.8337 (2)0.1358 (2)−0.2817 (3)0.0387 (7)
C10.8340 (3)0.0972 (3)−0.1428 (4)0.0472 (9)
H1B0.90070.0798−0.09170.057*
C20.7385 (3)0.0825 (3)−0.0737 (4)0.0485 (10)
H2A0.74100.05770.02430.058*
C30.6391 (3)0.1044 (3)−0.1492 (4)0.0413 (9)
H3A0.57380.0933−0.10380.050*
O10.4653 (2)0.3480 (2)−0.2803 (3)0.0550 (8)
O2−0.0055 (2)0.1263 (3)0.1929 (4)0.0669 (8)
N2−0.0802 (3)0.0813 (3)0.2490 (3)0.0427 (7)
O3−0.1439 (3)0.1264 (3)0.3279 (4)0.0735 (9)
O1W0.6452 (2)0.4755 (2)−0.2057 (4)0.0624 (8)
H1WA0.59320.4332−0.22670.075*
H1WB0.70330.4393−0.19280.075*
O4−0.0959 (3)−0.0117 (2)0.2228 (4)0.0702 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ag10.03123 (18)0.0563 (2)0.0621 (2)0.00455 (13)0.01775 (14)−0.00438 (15)
N30.0300 (16)0.0400 (18)0.0435 (18)0.0011 (13)0.0066 (13)−0.0052 (13)
C90.042 (2)0.034 (2)0.061 (3)0.0054 (17)0.0109 (19)−0.0029 (18)
C70.041 (2)0.033 (2)0.057 (2)−0.0023 (16)0.0209 (18)−0.0077 (16)
C80.039 (2)0.043 (2)0.055 (2)−0.0071 (17)0.0197 (18)−0.0027 (18)
C110.0277 (17)0.0366 (19)0.0319 (18)0.0012 (15)0.0013 (14)0.0008 (14)
C100.039 (2)0.035 (2)0.053 (2)−0.0021 (17)0.0105 (17)0.0004 (17)
C120.0267 (18)0.042 (2)0.0363 (19)−0.0045 (16)0.0048 (14)−0.0007 (16)
N40.0270 (15)0.0483 (19)0.0448 (18)−0.0020 (13)0.0127 (13)−0.0045 (14)
C130.032 (2)0.062 (3)0.041 (2)0.0028 (18)0.0105 (16)−0.0027 (17)
C40.0324 (19)0.0360 (18)0.0324 (18)0.0020 (15)0.0060 (15)−0.0046 (14)
C50.0305 (18)0.041 (2)0.0373 (19)0.0019 (15)0.0103 (15)0.0014 (15)
N10.0285 (16)0.0443 (17)0.0447 (18)−0.0018 (14)0.0108 (13)0.0025 (14)
C10.036 (2)0.056 (3)0.050 (2)0.0012 (18)0.0028 (17)0.0017 (19)
C20.045 (2)0.066 (3)0.036 (2)0.002 (2)0.0075 (17)0.0058 (18)
C30.037 (2)0.048 (2)0.041 (2)−0.0032 (17)0.0150 (16)−0.0004 (17)
O10.0404 (16)0.0537 (17)0.073 (2)−0.0142 (13)0.0212 (14)−0.0028 (14)
O20.055 (2)0.068 (2)0.080 (2)−0.0126 (16)0.0235 (16)0.0100 (18)
N20.0371 (18)0.050 (2)0.0413 (18)−0.0045 (15)0.0028 (14)0.0039 (15)
O30.066 (2)0.076 (2)0.082 (2)−0.0028 (18)0.0310 (18)−0.0178 (18)
O1W0.0471 (17)0.0461 (17)0.094 (2)−0.0057 (14)0.0067 (15)−0.0046 (15)
O40.068 (2)0.0443 (18)0.098 (3)−0.0020 (16)0.0053 (18)0.0006 (16)
Geometric parameters (Å, °) top
Ag1—N1i2.152 (3)C13—H13A0.9700
Ag1—N32.157 (3)C13—H13B0.9700
N3—C81.324 (5)C4—C51.369 (5)
N3—C91.328 (5)C4—C31.382 (5)
C9—C101.363 (5)C5—N11.331 (4)
C9—H9A0.9300C5—H5A0.9300
C7—C81.369 (5)N1—C11.336 (5)
C7—C111.378 (5)N1—Ag1ii2.152 (3)
C7—H7A0.9300C1—C21.368 (5)
C8—H8A0.9300C1—H1B0.9300
C11—C101.381 (5)C2—C31.370 (5)
C11—C121.497 (5)C2—H2A0.9300
C10—H10A0.9300C3—H3A0.9300
C12—O11.222 (4)O2—N21.220 (4)
C12—N41.331 (4)N2—O31.234 (4)
N4—C131.447 (5)N2—O41.245 (4)
N4—H4A0.8600O1W—H1WA0.8499
C13—C41.508 (5)O1W—H1WB0.8500
N1i—Ag1—N3172.19 (11)C4—C13—H13A108.7
C8—N3—C9117.3 (3)N4—C13—H13B108.7
C8—N3—Ag1122.0 (2)C4—C13—H13B108.7
C9—N3—Ag1120.5 (2)H13A—C13—H13B107.6
N3—C9—C10123.3 (3)C5—C4—C3117.3 (3)
N3—C9—H9A118.3C5—C4—C13119.3 (3)
C10—C9—H9A118.3C3—C4—C13123.3 (3)
C8—C7—C11119.8 (3)N1—C5—C4124.2 (3)
C8—C7—H7A120.1N1—C5—H5A117.9
C11—C7—H7A120.1C4—C5—H5A117.9
N3—C8—C7123.0 (3)C5—N1—C1117.8 (3)
N3—C8—H8A118.5C5—N1—Ag1ii120.4 (2)
C7—C8—H8A118.5C1—N1—Ag1ii121.6 (2)
C7—C11—C10117.0 (3)N1—C1—C2121.7 (4)
C7—C11—C12124.8 (3)N1—C1—H1B119.2
C10—C11—C12118.3 (3)C2—C1—H1B119.2
C9—C10—C11119.6 (4)C1—C2—C3120.0 (4)
C9—C10—H10A120.2C1—C2—H2A120.0
C11—C10—H10A120.2C3—C2—H2A120.0
O1—C12—N4122.4 (3)C2—C3—C4119.0 (3)
O1—C12—C11120.8 (3)C2—C3—H3A120.5
N4—C12—C11116.8 (3)C4—C3—H3A120.5
C12—N4—C13121.5 (3)O2—N2—O3121.6 (4)
C12—N4—H4A119.2O2—N2—O4119.9 (4)
C13—N4—H4A119.2O3—N2—O4118.4 (3)
N4—C13—C4114.1 (3)H1WA—O1W—H1WB105.6
N4—C13—H13A108.7
C8—N3—C9—C10−0.2 (6)C11—C12—N4—C13−179.1 (3)
Ag1—N3—C9—C10−175.6 (3)C12—N4—C13—C487.7 (4)
C9—N3—C8—C70.6 (6)N4—C13—C4—C5−160.2 (3)
Ag1—N3—C8—C7175.9 (3)N4—C13—C4—C323.9 (5)
C11—C7—C8—N3−0.5 (7)C3—C4—C5—N11.0 (5)
C8—C7—C11—C10−0.1 (6)C13—C4—C5—N1−175.1 (3)
C8—C7—C11—C12178.4 (4)C4—C5—N1—C1−0.2 (5)
N3—C9—C10—C11−0.3 (6)C4—C5—N1—Ag1ii−174.5 (3)
C7—C11—C10—C90.4 (6)C5—N1—C1—C2−1.5 (6)
C12—C11—C10—C9−178.1 (3)Ag1ii—N1—C1—C2172.8 (3)
C7—C11—C12—O1−171.7 (4)N1—C1—C2—C32.2 (6)
C10—C11—C12—O16.7 (5)C1—C2—C3—C4−1.3 (6)
C7—C11—C12—N47.3 (6)C5—C4—C3—C2−0.3 (5)
C10—C11—C12—N4−174.2 (3)C13—C4—C3—C2175.7 (4)
O1—C12—N4—C130.0 (6)
Symmetry codes: (i) x−1, −y+1/2, z+1/2; (ii) x+1, −y+1/2, z−1/2.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N4—H4A···O1Wiii0.862.042.837 (4)154
O1W—H1WA···O10.851.942.790 (4)174
O1W—H1WB···O3ii0.852.042.886 (4)171
Symmetry codes: (iii) −x+1, y−1/2, −z−1/2; (ii) x+1, −y+1/2, z−1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N4—H4A···O1Wi0.862.042.837 (4)154
O1W—H1WA···O10.851.942.790 (4)174
O1W—H1WB···O3ii0.852.042.886 (4)171
Symmetry codes: (i) −x+1, y−1/2, −z−1/2; (ii) x+1, −y+1/2, z−1/2.
references
References top

Cordes, D. B. & Hanton, L. R. (2007). Inorg. Chem. 46, 1634–1644.

Kumar, D. K., Das, A. & Dastidar, P. (2006). Cryst. Growth Des. 6, 1903–1909.

Rigaku/MSC (2003). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.

Sheldrick, G. M. (1997). SHELXL97 and SHELXS97. University of Göttingen, Germany.

Sheldrick, G. M. (1999). SHELXTL. Version 5.1. Bruker AXS Inc., Madison, Wisconsin, USA.

Tong, M.-L., Wu, Y.-M., Ru, J., Chen, X.-M., Chang, H.-C. & Kitagawa, S. (2002). Inorg. Chem. 41, 4846–4848.