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Acta Cryst. (2008). E64, m470    [ doi:10.1107/S1600536807049082 ]

catena-Poly[[silver(I)-[mu]-[N-(4-pyridylmethyl)pyridine-4-carboxamide-[kappa]2N:N']] nitrate monohydrate]

Y.-T. Ma, B.-W. Sun and S. W. Ng

Abstract top

The title coordination polymer, {[Ag(C12H11N3O)]NO3·H2O}n, has a polycationic chain motif in which the Ag atom is bridged by the heterocyclic ligand; the Ag atom shows linear coordination. If the two long Ag...Onitrate interactions [2.794 (6) and 2.867 (5) Å] are regarded as bonds, the compound adopts a three-dimensional network structure. 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 4-C5H4N–CH2–NH–C(O)–4-C5H4N ligand is a spacer heterocycle that should function like 4,4'-bipyridine, which forms numerous coordination polymers, but should be flexible. There is, however, only one crystal structure report of an adduct, a hydrated disilver oxalate adduct (Tong et al., 2002). The title silver nitrate adduct has the metal in a linear enviroment, but 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 adopts a three-dimensional network structure.

Related literature top

For the structure of the hydrated disilver oxalate adduct of the heterocyclic ligand, see Tong et al. (2002).

Experimental top

An aqueous solution (5 ml) of silver nitrate (1.0 mmol) was layed over a methanol (5 ml) solution of N-(4-pyridylmethyl)-4-pyridinecarboxamide (1.0 mmol) in a thin tube. The tube was placed vertically and kept away from light. Colorless crystals were obtained after two weeks. These were washed with methanol and collected in 50% yield. CH&N elemental analysis. Found: C 35.88, H 3.53, N 13.76%; calc. for C12H13AgN4O5: C 35.93, H 3.27, N 13.96%.

Refinement top

Carbon-bound H-atoms were placed in idealized positions and constrained to ride on their parent atoms, with C—H distances of 0.93–0.97 Å and U(H) set to 1.2Ueq(C). The amino and water H-atoms were located in a difference Fourier map, and were refined with a distance restraint of N—H = O—H = 0.85 (1) Å.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2007).

Figures top
[Figure 1] Fig. 1. A portion of the chain structure. Ellipsoids are drawn at the 50% probability level, and H atoms of spheres of arbitry radius. The red dashed lines denote the long Ag···O bonds and the dashed cyan line denotes the hydrogen bond. Symmetry codes (i) = 1/2 - x, 1 - y, z - 1/2; (ii) x - 1/2, 3/2 - y, -z.
catena-Poly[[silver(I)-µ-[N-(4-pyridylmethyl)pyridine-4- carboxamide-κ2N:N']] nitrate monohydrate] top
Crystal data top
[Ag(C12H11N3O)]NO3·H2OF000 = 1600
Mr = 401.13Dx = 1.879 Mg m−3
Orthorhombic, PbcaMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 5655 reflections
a = 12.912 (7) Åθ = 3.2–27.5º
b = 9.021 (5) ŵ = 1.45 mm−1
c = 24.52 (1) ÅT = 295 (2) K
V = 2856 (3) Å3Column, colourless
Z = 80.6 × 0.4 × 0.2 mm
Data collection top
Rigaku Mercury
diffractometer		3249 independent reflections
Radiation source: medium-focus sealed tube2433 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.047
T = 295(2) Kθmax = 27.5º
ω scansθmin = 3.2º
Absorption correction: multi-scan
(Jacobson, 1998)		h = −16→16
Tmin = 0.50, Tmax = 0.75k = −11→11
25888 measured reflectionsl = −30→31
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)] = 0.053H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.141  w = 1/[σ2(Fo2) + (0.0589P)2 + 5.5451P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
3249 reflectionsΔρmax = 0.91 e Å−3
211 parametersΔρmin = −0.75 e Å−3
3 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
[Ag(C12H11N3O)]NO3·H2OV = 2856 (3) Å3
Mr = 401.13Z = 8
Orthorhombic, PbcaMo Kα
a = 12.912 (7) ŵ = 1.45 mm−1
b = 9.021 (5) ÅT = 295 (2) K
c = 24.52 (1) Å0.6 × 0.4 × 0.2 mm
Data collection top
Rigaku Mercury
diffractometer		3249 independent reflections
Absorption correction: multi-scan
(Jacobson, 1998)		2433 reflections with I > 2σ(I)
Tmin = 0.50, Tmax = 0.75Rint = 0.047
25888 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0533 restraints
wR(F2) = 0.141H atoms treated by a mixture of
independent and constrained refinement
S = 1.06Δρmax = 0.91 e Å−3
3249 reflectionsΔρmin = −0.75 e Å−3
211 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ag10.16581 (3)0.61149 (5)0.002207 (15)0.05996 (18)
O10.1859 (3)0.1438 (4)0.23653 (13)0.0598 (9)
O20.3756 (4)0.6914 (6)0.00374 (16)0.0905 (14)
O30.5035 (4)0.7095 (7)−0.0481 (2)0.1077 (17)
O40.3682 (5)0.8329 (7)−0.0644 (2)0.118 (2)
O1W0.5539 (3)0.2042 (5)0.17401 (17)0.0660 (10)
H1W10.608 (3)0.189 (8)0.193 (2)0.10 (2)*
H1W20.562 (8)0.176 (10)0.1412 (13)0.15 (4)*
N10.1990 (3)0.4795 (4)0.07408 (14)0.0448 (8)
N20.3572 (3)0.1578 (4)0.22161 (14)0.0458 (9)
H2N0.408 (3)0.198 (5)0.2048 (19)0.061 (16)*
N30.3656 (3)0.2837 (4)0.42466 (15)0.0470 (9)
N40.4163 (3)0.7500 (4)−0.03557 (16)0.0469 (9)
C10.1231 (4)0.4240 (6)0.1046 (2)0.0567 (12)
H10.05510.45060.09670.068*
C20.1412 (4)0.3281 (6)0.14763 (19)0.0528 (12)
H20.08590.28950.16740.063*
C30.2413 (3)0.2900 (4)0.16112 (14)0.0377 (9)
C40.3201 (4)0.3498 (6)0.1298 (2)0.0524 (12)
H40.38900.32790.13760.063*
C50.2952 (4)0.4425 (6)0.08692 (19)0.0513 (11)
H50.34890.48090.06590.062*
C60.2592 (4)0.1894 (5)0.20953 (15)0.0417 (9)
C70.3844 (4)0.0665 (5)0.26853 (17)0.0487 (11)
H7A0.45470.03070.26390.058*
H7B0.3390−0.01910.26940.058*
C80.3770 (3)0.1465 (4)0.32274 (16)0.0379 (9)
C90.3479 (4)0.2929 (5)0.32757 (19)0.0474 (11)
H9A0.33250.34860.29670.057*
C100.3418 (4)0.3559 (5)0.3786 (2)0.0515 (12)
H100.32010.45400.38120.062*
C110.3960 (4)0.1419 (5)0.41994 (18)0.0514 (11)
H110.41340.08950.45130.062*
C120.4021 (4)0.0715 (5)0.37027 (17)0.0482 (11)
H120.4233−0.02700.36860.058*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ag10.0659 (3)0.0671 (3)0.0469 (3)0.00106 (19)−0.01097 (16)0.01944 (19)
O10.065 (2)0.074 (2)0.0410 (18)−0.0126 (18)0.0093 (16)0.0097 (17)
O20.111 (4)0.103 (4)0.058 (3)−0.013 (3)0.013 (2)0.026 (2)
O30.076 (3)0.171 (5)0.076 (3)0.009 (3)0.003 (2)−0.016 (3)
O40.130 (4)0.135 (5)0.089 (4)0.049 (4)0.001 (3)0.050 (3)
O1W0.056 (2)0.087 (3)0.055 (2)0.005 (2)−0.0059 (19)0.011 (2)
N10.052 (2)0.048 (2)0.0343 (18)0.0005 (18)−0.0060 (16)0.0031 (16)
N20.058 (2)0.047 (2)0.0318 (18)0.0024 (19)0.0050 (17)0.0092 (16)
N30.053 (2)0.049 (2)0.0394 (19)−0.0026 (18)−0.0003 (17)−0.0094 (17)
N40.053 (2)0.048 (2)0.041 (2)−0.0017 (19)0.0040 (18)0.0014 (17)
C10.047 (3)0.071 (3)0.052 (3)0.001 (2)−0.008 (2)0.014 (2)
C20.046 (2)0.071 (3)0.041 (2)−0.011 (2)−0.0001 (19)0.006 (2)
C30.049 (2)0.037 (2)0.0265 (17)−0.0034 (19)0.0008 (17)−0.0015 (15)
C40.043 (2)0.063 (3)0.051 (3)0.007 (2)0.005 (2)0.018 (2)
C50.045 (2)0.059 (3)0.049 (3)0.005 (2)0.007 (2)0.022 (2)
C60.056 (3)0.043 (2)0.0255 (18)−0.004 (2)0.0057 (18)−0.0009 (16)
C70.071 (3)0.043 (2)0.032 (2)0.008 (2)−0.001 (2)0.0033 (18)
C80.043 (2)0.037 (2)0.0333 (19)−0.0026 (18)−0.0003 (17)−0.0010 (16)
C90.057 (3)0.041 (2)0.044 (2)0.005 (2)−0.009 (2)−0.0001 (19)
C100.057 (3)0.043 (2)0.054 (3)0.006 (2)−0.006 (2)−0.009 (2)
C110.073 (3)0.046 (3)0.035 (2)0.001 (2)−0.005 (2)−0.0004 (19)
C120.069 (3)0.037 (2)0.039 (2)0.004 (2)0.002 (2)0.0023 (18)
Geometric parameters (Å, °) top
Ag1—N3i2.162 (4)C2—C31.377 (6)
Ag1—N12.170 (4)C2—H20.9300
Ag1—O22.803 (6)C3—C41.385 (6)
Ag1—O3ii2.874 (6)C3—C61.512 (5)
O1—C61.226 (5)C4—C51.381 (6)
O2—N41.219 (5)C4—H40.9300
O3—N41.223 (6)C5—H50.9300
O4—N41.202 (6)C7—C81.516 (6)
O1W—H1W10.85 (4)C7—H7A0.9700
O1W—H1W20.85 (4)C7—H7B0.9700
N1—C51.325 (6)C8—C91.378 (6)
N1—C11.331 (6)C8—C121.386 (6)
N2—C61.330 (6)C9—C101.377 (6)
N2—C71.458 (5)C9—H9A0.9300
N2—H2N0.86 (4)C10—H100.9300
N3—C101.340 (6)C11—C121.376 (6)
N3—C111.343 (6)C11—H110.9300
C1—C21.385 (7)C12—H120.9300
C1—H10.9300
N3i—Ag1—N1172.52 (14)C5—C4—H4120.4
N3i—Ag1—O294.61 (13)C3—C4—H4120.4
N1—Ag1—O286.53 (14)N1—C5—C4123.5 (4)
N3i—Ag1—O3ii87.80 (15)N1—C5—H5118.3
N1—Ag1—O3ii97.73 (15)C4—C5—H5118.3
O2—Ag1—O3ii123.69 (16)O1—C6—N2122.8 (4)
N4—O2—Ag1121.2 (4)O1—C6—C3120.5 (4)
H1W1—O1W—H1W2111 (8)N2—C6—C3116.7 (4)
C5—N1—C1117.5 (4)N2—C7—C8114.0 (4)
C5—N1—Ag1121.1 (3)N2—C7—H7A108.7
C1—N1—Ag1121.2 (3)C8—C7—H7A108.7
C6—N2—C7121.8 (4)N2—C7—H7B108.7
C6—N2—H2N122 (4)C8—C7—H7B108.7
C7—N2—H2N116 (4)H7A—C7—H7B107.6
C10—N3—C11117.2 (4)C9—C8—C12117.4 (4)
C10—N3—Ag1iii119.1 (3)C9—C8—C7123.3 (4)
C11—N3—Ag1iii123.2 (3)C12—C8—C7119.3 (4)
O4—N4—O2120.8 (5)C10—C9—C8119.3 (4)
O4—N4—O3120.9 (5)C10—C9—H9A120.4
O2—N4—O3117.8 (5)C8—C9—H9A120.4
N1—C1—C2122.6 (5)N3—C10—C9123.5 (4)
N1—C1—H1118.7N3—C10—H10118.2
C2—C1—H1118.7C9—C10—H10118.2
C3—C2—C1119.8 (4)N3—C11—C12122.2 (4)
C3—C2—H2120.1N3—C11—H11118.9
C1—C2—H2120.1C12—C11—H11118.9
C2—C3—C4117.4 (4)C11—C12—C8120.3 (4)
C2—C3—C6118.8 (4)C11—C12—H12119.8
C4—C3—C6123.8 (4)C8—C12—H12119.8
C5—C4—C3119.1 (4)
N3i—Ag1—O2—N4−7.1 (5)C7—N2—C6—O1−0.4 (7)
N1—Ag1—O2—N4165.5 (5)C7—N2—C6—C3177.7 (4)
O3ii—Ag1—O2—N4−97.5 (4)C2—C3—C6—O1−0.7 (6)
O2—Ag1—N1—C5−17.8 (4)C4—C3—C6—O1177.8 (4)
O3ii—Ag1—N1—C5−141.4 (4)C2—C3—C6—N2−178.8 (4)
O2—Ag1—N1—C1167.1 (4)C4—C3—C6—N2−0.3 (6)
O3ii—Ag1—N1—C143.5 (4)C6—N2—C7—C8−76.5 (6)
Ag1—O2—N4—O433.5 (7)N2—C7—C8—C9−0.5 (7)
Ag1—O2—N4—O3−138.7 (4)N2—C7—C8—C12−179.3 (4)
C5—N1—C1—C2−1.5 (8)C12—C8—C9—C10−2.1 (7)
Ag1—N1—C1—C2173.8 (4)C7—C8—C9—C10179.1 (4)
N1—C1—C2—C31.7 (8)C11—N3—C10—C9−0.6 (7)
C1—C2—C3—C4−0.7 (7)Ag1iii—N3—C10—C9−172.5 (4)
C1—C2—C3—C6177.9 (4)C8—C9—C10—N31.9 (7)
C2—C3—C4—C5−0.5 (7)C10—N3—C11—C12−0.5 (7)
C6—C3—C4—C5−179.0 (4)Ag1iii—N3—C11—C12171.1 (4)
C1—N1—C5—C40.2 (8)N3—C11—C12—C80.2 (8)
Ag1—N1—C5—C4−175.1 (4)C9—C8—C12—C111.1 (7)
C3—C4—C5—N10.8 (8)C7—C8—C12—C11180.0 (5)
Symmetry codes: (i) −x+1/2, −y+1, z−1/2; (ii) x−1/2, −y+3/2, −z; (iii) −x+1/2, −y+1, z+1/2.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2N···O1W0.86 (4)2.04 (2)2.827 (6)154 (5)
O1W—H1W1···O1iv0.85 (4)2.05 (3)2.831 (5)154 (7)
O1W—H1W2···O4v0.85 (4)2.09 (4)2.888 (7)157 (9)
Symmetry codes: (iv) x+1/2, y, −z+1/2; (v) −x+1, −y+1, −z.
Table 1
Selected geometric parameters (Å) top
Ag1—N3i2.162 (4)Ag1—O22.803 (6)
Ag1—N12.170 (4)Ag1—O3ii2.874 (6)
Symmetry codes: (i) −x+1/2, −y+1, z−1/2; (ii) x−1/2, −y+3/2, −z.
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2N···O1W0.86 (4)2.04 (2)2.827 (6)154 (5)
O1W—H1W1···O1iii0.85 (4)2.05 (3)2.831 (5)154 (7)
O1W—H1W2···O4iv0.85 (4)2.09 (4)2.888 (7)157 (9)
Symmetry codes: (iii) x+1/2, y, −z+1/2; (iv) −x+1, −y+1, −z.
Acknowledgements top

The authors thank Southeast University, China, and the University of Malaya for supporting this study.

references
References top

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.

Jacobson, R. (1998). Private communication to Rigaku Corporation, Tokyo, Japan.

Rigaku/MSC (2005). CrystalClear. Version 1.4.0. Rigaku/MSC, The Woodlands, Texas, USA.

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

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

Westrip, S. P. (2007). publCIF. In preparation.