metal-organic compounds
catena-Poly[[silver(I)-μ-N-(3-pyridylmethyl)pyridine-4-carboxamide] nitrate monohydrate]
aSchool of Chemical Science and Technology, Key Laboratory of Medicinal Chemistry for Natural Resources, Ministry of Education, Yunnan University, Kunming 650091, People's Republic of China
*Correspondence e-mail: qhzhao@ynu.edu.cn
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.
Related literature
For related literature, see: Cordes & Hanton (2007); Kumar et al. (2006); Tong et al. (2002).
Experimental
Crystal data
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Refinement
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Data collection: CrystalClear (Rigaku/MSC, 2003); cell CrystalClear; data reduction: CrystalClear; 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.
Supporting information
https://doi.org/10.1107/S1600536807064744/pk2069sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807064744/pk2069Isup2.hkl
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%.
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).
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).
For related literature, see: Cordes & Hanton (2007); Kumar et al. (2006); Tong et al. (2002).
Data collection: CrystalClear (Rigaku/MSC, 2003); cell
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).[Ag(C12H11N3O)]NO3·H2O | F(000) = 800 |
Mr = 401.13 | Dx = 1.891 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 5866 reflections |
a = 12.177 (2) Å | θ = 3.2–27.5° |
b = 13.022 (3) Å | µ = 1.46 mm−1 |
c = 8.9109 (18) Å | T = 293 K |
β = 94.21 (3)° | Block, colorless |
V = 1409.2 (5) Å3 | 0.6 × 0.4 × 0.2 mm |
Z = 4 |
Rigaku Mercury CCD diffractometer | 3230 independent reflections |
Radiation source: fine-focus sealed tube | 2399 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.065 |
ω scans | θmax = 27.5°, θmin = 3.1° |
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2003) | h = −15→15 |
Tmin = 0.503, Tmax = 0.742 | k = −16→16 |
14304 measured reflections | l = −11→11 |
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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.101 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0433P)2 + 0.2355P] where P = (Fo2 + 2Fc2)/3 |
3230 reflections | (Δ/σ)max < 0.001 |
199 parameters | Δρmax = 0.35 e Å−3 |
0 restraints | Δρmin = −0.43 e Å−3 |
[Ag(C12H11N3O)]NO3·H2O | V = 1409.2 (5) Å3 |
Mr = 401.13 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.177 (2) Å | µ = 1.46 mm−1 |
b = 13.022 (3) Å | T = 293 K |
c = 8.9109 (18) Å | 0.6 × 0.4 × 0.2 mm |
β = 94.21 (3)° |
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 = 0.742 | Rint = 0.065 |
14304 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | 0 restraints |
wR(F2) = 0.101 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.35 e Å−3 |
3230 reflections | Δρmin = −0.43 e Å−3 |
199 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Ag1 | −0.01568 (2) | 0.32484 (2) | 0.11987 (4) | 0.04917 (14) | |
N3 | 0.1306 (2) | 0.3030 (2) | 0.0011 (3) | 0.0377 (7) | |
C9 | 0.1867 (3) | 0.3832 (3) | −0.0444 (4) | 0.0453 (9) | |
H9A | 0.1644 | 0.4486 | −0.0176 | 0.054* | |
C7 | 0.2524 (3) | 0.1954 (3) | −0.1219 (4) | 0.0426 (9) | |
H7A | 0.2731 | 0.1291 | −0.1467 | 0.051* | |
C8 | 0.1637 (3) | 0.2107 (3) | −0.0387 (4) | 0.0448 (9) | |
H8A | 0.1249 | 0.1537 | −0.0087 | 0.054* | |
C11 | 0.3109 (3) | 0.2785 (3) | −0.1690 (4) | 0.0321 (7) | |
C10 | 0.2755 (3) | 0.3746 (3) | −0.1283 (4) | 0.0418 (9) | |
H10A | 0.3120 | 0.4331 | −0.1580 | 0.050* | |
C12 | 0.4107 (3) | 0.2716 (3) | −0.2571 (4) | 0.0348 (8) | |
N4 | 0.4370 (2) | 0.1789 (2) | −0.3061 (3) | 0.0396 (7) | |
H4A | 0.3962 | 0.1273 | −0.2872 | 0.047* | |
C13 | 0.5327 (3) | 0.1630 (3) | −0.3904 (4) | 0.0444 (9) | |
H13A | 0.5431 | 0.2231 | −0.4520 | 0.053* | |
H13B | 0.5188 | 0.1051 | −0.4576 | 0.053* | |
C4 | 0.6375 (3) | 0.1431 (3) | −0.2938 (4) | 0.0335 (8) | |
C5 | 0.7368 (3) | 0.1578 (3) | −0.3533 (4) | 0.0358 (8) | |
H5A | 0.7365 | 0.1849 | −0.4499 | 0.043* | |
N1 | 0.8337 (2) | 0.1358 (2) | −0.2817 (3) | 0.0387 (7) | |
C1 | 0.8340 (3) | 0.0972 (3) | −0.1428 (4) | 0.0472 (9) | |
H1B | 0.9007 | 0.0798 | −0.0917 | 0.057* | |
C2 | 0.7385 (3) | 0.0825 (3) | −0.0737 (4) | 0.0485 (10) | |
H2A | 0.7410 | 0.0577 | 0.0243 | 0.058* | |
C3 | 0.6391 (3) | 0.1044 (3) | −0.1492 (4) | 0.0413 (9) | |
H3A | 0.5738 | 0.0933 | −0.1038 | 0.050* | |
O1 | 0.4653 (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) | |
O1W | 0.6452 (2) | 0.4755 (2) | −0.2057 (4) | 0.0624 (8) | |
H1WA | 0.5932 | 0.4332 | −0.2267 | 0.075* | |
H1WB | 0.7033 | 0.4393 | −0.1928 | 0.075* | |
O4 | −0.0959 (3) | −0.0117 (2) | 0.2228 (4) | 0.0702 (9) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ag1 | 0.03123 (18) | 0.0563 (2) | 0.0621 (2) | 0.00455 (13) | 0.01775 (14) | −0.00438 (15) |
N3 | 0.0300 (16) | 0.0400 (18) | 0.0435 (18) | 0.0011 (13) | 0.0066 (13) | −0.0052 (13) |
C9 | 0.042 (2) | 0.034 (2) | 0.061 (3) | 0.0054 (17) | 0.0109 (19) | −0.0029 (18) |
C7 | 0.041 (2) | 0.033 (2) | 0.057 (2) | −0.0023 (16) | 0.0209 (18) | −0.0077 (16) |
C8 | 0.039 (2) | 0.043 (2) | 0.055 (2) | −0.0071 (17) | 0.0197 (18) | −0.0027 (18) |
C11 | 0.0277 (17) | 0.0366 (19) | 0.0319 (18) | 0.0012 (15) | 0.0013 (14) | 0.0008 (14) |
C10 | 0.039 (2) | 0.035 (2) | 0.053 (2) | −0.0021 (17) | 0.0105 (17) | 0.0004 (17) |
C12 | 0.0267 (18) | 0.042 (2) | 0.0363 (19) | −0.0045 (16) | 0.0048 (14) | −0.0007 (16) |
N4 | 0.0270 (15) | 0.0483 (19) | 0.0448 (18) | −0.0020 (13) | 0.0127 (13) | −0.0045 (14) |
C13 | 0.032 (2) | 0.062 (3) | 0.041 (2) | 0.0028 (18) | 0.0105 (16) | −0.0027 (17) |
C4 | 0.0324 (19) | 0.0360 (18) | 0.0324 (18) | 0.0020 (15) | 0.0060 (15) | −0.0046 (14) |
C5 | 0.0305 (18) | 0.041 (2) | 0.0373 (19) | 0.0019 (15) | 0.0103 (15) | 0.0014 (15) |
N1 | 0.0285 (16) | 0.0443 (17) | 0.0447 (18) | −0.0018 (14) | 0.0108 (13) | 0.0025 (14) |
C1 | 0.036 (2) | 0.056 (3) | 0.050 (2) | 0.0012 (18) | 0.0028 (17) | 0.0017 (19) |
C2 | 0.045 (2) | 0.066 (3) | 0.036 (2) | 0.002 (2) | 0.0075 (17) | 0.0058 (18) |
C3 | 0.037 (2) | 0.048 (2) | 0.041 (2) | −0.0032 (17) | 0.0150 (16) | −0.0004 (17) |
O1 | 0.0404 (16) | 0.0537 (17) | 0.073 (2) | −0.0142 (13) | 0.0212 (14) | −0.0028 (14) |
O2 | 0.055 (2) | 0.068 (2) | 0.080 (2) | −0.0126 (16) | 0.0235 (16) | 0.0100 (18) |
N2 | 0.0371 (18) | 0.050 (2) | 0.0413 (18) | −0.0045 (15) | 0.0028 (14) | 0.0039 (15) |
O3 | 0.066 (2) | 0.076 (2) | 0.082 (2) | −0.0028 (18) | 0.0310 (18) | −0.0178 (18) |
O1W | 0.0471 (17) | 0.0461 (17) | 0.094 (2) | −0.0057 (14) | 0.0067 (15) | −0.0046 (15) |
O4 | 0.068 (2) | 0.0443 (18) | 0.098 (3) | −0.0020 (16) | 0.0053 (18) | 0.0006 (16) |
Ag1—N1i | 2.152 (3) | C13—H13A | 0.9700 |
Ag1—N3 | 2.157 (3) | C13—H13B | 0.9700 |
N3—C8 | 1.324 (5) | C4—C5 | 1.369 (5) |
N3—C9 | 1.328 (5) | C4—C3 | 1.382 (5) |
C9—C10 | 1.363 (5) | C5—N1 | 1.331 (4) |
C9—H9A | 0.9300 | C5—H5A | 0.9300 |
C7—C8 | 1.369 (5) | N1—C1 | 1.336 (5) |
C7—C11 | 1.378 (5) | N1—Ag1ii | 2.152 (3) |
C7—H7A | 0.9300 | C1—C2 | 1.368 (5) |
C8—H8A | 0.9300 | C1—H1B | 0.9300 |
C11—C10 | 1.381 (5) | C2—C3 | 1.370 (5) |
C11—C12 | 1.497 (5) | C2—H2A | 0.9300 |
C10—H10A | 0.9300 | C3—H3A | 0.9300 |
C12—O1 | 1.222 (4) | O2—N2 | 1.220 (4) |
C12—N4 | 1.331 (4) | N2—O3 | 1.234 (4) |
N4—C13 | 1.447 (5) | N2—O4 | 1.245 (4) |
N4—H4A | 0.8600 | O1W—H1WA | 0.8499 |
C13—C4 | 1.508 (5) | O1W—H1WB | 0.8500 |
N1i—Ag1—N3 | 172.19 (11) | C4—C13—H13A | 108.7 |
C8—N3—C9 | 117.3 (3) | N4—C13—H13B | 108.7 |
C8—N3—Ag1 | 122.0 (2) | C4—C13—H13B | 108.7 |
C9—N3—Ag1 | 120.5 (2) | H13A—C13—H13B | 107.6 |
N3—C9—C10 | 123.3 (3) | C5—C4—C3 | 117.3 (3) |
N3—C9—H9A | 118.3 | C5—C4—C13 | 119.3 (3) |
C10—C9—H9A | 118.3 | C3—C4—C13 | 123.3 (3) |
C8—C7—C11 | 119.8 (3) | N1—C5—C4 | 124.2 (3) |
C8—C7—H7A | 120.1 | N1—C5—H5A | 117.9 |
C11—C7—H7A | 120.1 | C4—C5—H5A | 117.9 |
N3—C8—C7 | 123.0 (3) | C5—N1—C1 | 117.8 (3) |
N3—C8—H8A | 118.5 | C5—N1—Ag1ii | 120.4 (2) |
C7—C8—H8A | 118.5 | C1—N1—Ag1ii | 121.6 (2) |
C7—C11—C10 | 117.0 (3) | N1—C1—C2 | 121.7 (4) |
C7—C11—C12 | 124.8 (3) | N1—C1—H1B | 119.2 |
C10—C11—C12 | 118.3 (3) | C2—C1—H1B | 119.2 |
C9—C10—C11 | 119.6 (4) | C1—C2—C3 | 120.0 (4) |
C9—C10—H10A | 120.2 | C1—C2—H2A | 120.0 |
C11—C10—H10A | 120.2 | C3—C2—H2A | 120.0 |
O1—C12—N4 | 122.4 (3) | C2—C3—C4 | 119.0 (3) |
O1—C12—C11 | 120.8 (3) | C2—C3—H3A | 120.5 |
N4—C12—C11 | 116.8 (3) | C4—C3—H3A | 120.5 |
C12—N4—C13 | 121.5 (3) | O2—N2—O3 | 121.6 (4) |
C12—N4—H4A | 119.2 | O2—N2—O4 | 119.9 (4) |
C13—N4—H4A | 119.2 | O3—N2—O4 | 118.4 (3) |
N4—C13—C4 | 114.1 (3) | H1WA—O1W—H1WB | 105.6 |
N4—C13—H13A | 108.7 | ||
C8—N3—C9—C10 | −0.2 (6) | C11—C12—N4—C13 | −179.1 (3) |
Ag1—N3—C9—C10 | −175.6 (3) | C12—N4—C13—C4 | 87.7 (4) |
C9—N3—C8—C7 | 0.6 (6) | N4—C13—C4—C5 | −160.2 (3) |
Ag1—N3—C8—C7 | 175.9 (3) | N4—C13—C4—C3 | 23.9 (5) |
C11—C7—C8—N3 | −0.5 (7) | C3—C4—C5—N1 | 1.0 (5) |
C8—C7—C11—C10 | −0.1 (6) | C13—C4—C5—N1 | −175.1 (3) |
C8—C7—C11—C12 | 178.4 (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—C9 | 0.4 (6) | C5—N1—C1—C2 | −1.5 (6) |
C12—C11—C10—C9 | −178.1 (3) | Ag1ii—N1—C1—C2 | 172.8 (3) |
C7—C11—C12—O1 | −171.7 (4) | N1—C1—C2—C3 | 2.2 (6) |
C10—C11—C12—O1 | 6.7 (5) | C1—C2—C3—C4 | −1.3 (6) |
C7—C11—C12—N4 | 7.3 (6) | C5—C4—C3—C2 | −0.3 (5) |
C10—C11—C12—N4 | −174.2 (3) | C13—C4—C3—C2 | 175.7 (4) |
O1—C12—N4—C13 | 0.0 (6) |
Symmetry codes: (i) x−1, −y+1/2, z+1/2; (ii) x+1, −y+1/2, z−1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4A···O1Wiii | 0.86 | 2.04 | 2.837 (4) | 154 |
O1W—H1WA···O1 | 0.85 | 1.94 | 2.790 (4) | 174 |
O1W—H1WB···O3ii | 0.85 | 2.04 | 2.886 (4) | 171 |
Symmetry codes: (ii) x+1, −y+1/2, z−1/2; (iii) −x+1, y−1/2, −z−1/2. |
Experimental details
Crystal data | |
Chemical formula | [Ag(C12H11N3O)]NO3·H2O |
Mr | 401.13 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 12.177 (2), 13.022 (3), 8.9109 (18) |
β (°) | 94.21 (3) |
V (Å3) | 1409.2 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.46 |
Crystal size (mm) | 0.6 × 0.4 × 0.2 |
Data collection | |
Diffractometer | Rigaku Mercury CCD diffractometer |
Absorption correction | Multi-scan (CrystalClear; Rigaku/MSC, 2003) |
Tmin, Tmax | 0.503, 0.742 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14304, 3230, 2399 |
Rint | 0.065 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.101, 1.06 |
No. of reflections | 3230 |
No. of parameters | 199 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.35, −0.43 |
Computer programs: CrystalClear (Rigaku/MSC, 2003), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Sheldrick, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4A···O1Wi | 0.86 | 2.04 | 2.837 (4) | 153.7 |
O1W—H1WA···O1 | 0.85 | 1.94 | 2.790 (4) | 174.3 |
O1W—H1WB···O3ii | 0.85 | 2.04 | 2.886 (4) | 170.5 |
Symmetry codes: (i) −x+1, y−1/2, −z−1/2; (ii) x+1, −y+1/2, z−1/2. |
References
Cordes, D. B. & Hanton, L. R. (2007). Inorg. Chem. 46, 1634–1644. Web of Science CSD CrossRef PubMed CAS Google Scholar
Kumar, D. K., Das, A. & Dastidar, P. (2006). Cryst. Growth Des. 6, 1903–1909. Web of Science CSD CrossRef CAS Google Scholar
Rigaku/MSC (2003). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (1997). SHELXL97 and SHELXS97. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (1999). SHELXTL. Version 5.1. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Tong, M.-L., Wu, Y.-M., Ru, J., Chen, X.-M., Chang, H.-C. & Kitagawa, S. (2002). Inorg. Chem. 41, 4846–4848. Web of Science CSD CrossRef PubMed CAS Google Scholar
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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).