Abstract
In the title compound, [Ag2(C6H7N2O2S)2], the AgI atom is coordinated by two N atoms from two N-(pyridin-2-yl)methanesulfonamidate anions in a slightly bent linear geometry [N—Ag—N = 166.03 (7)°]. The AgI atoms are bridged by the N-(pyridin-2-yl)methanesulfonamidate anions, forming a centrosymmetric dinuclear molecule, in which the Ag⋯Ag distance is 2.7072 (4) Å.
Related literature
For related di(pyridyl/pyrimidyl)amide structures, see: Hu et al. (2004 ▶); Hsu et al. (2008 ▶); Yeh et al. (2008 ▶); Tsai et al. (2010 ▶). For related methyl-4-(pyridin-pyrimidin-2-ylcarbamoyl)benzoate structures, see: Wu et al. (2011 ▶); Hsiao et al. (2012 ▶). For related phosphinic amide structures, see: Yeh & Chen (2011 ▶); Yeh et al. (2012 ▶).
Experimental
Crystal data
[Ag2(C6H7N2O2S)2]
M r = 558.13
Monoclinic,
a = 6.4406 (2) Å
b = 15.4580 (5) Å
c = 8.0789 (2) Å
β = 97.143 (2)°
V = 798.08 (4) Å3
Z = 2
Mo Kα radiation
μ = 2.74 mm−1
T = 296 K
0.20 × 0.10 × 0.10 mm
Data collection
Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.636, T max = 0.747
12917 measured reflections
3569 independent reflections
2732 reflections with I > 2σ(I)
R int = 0.048
Refinement
R[F 2 > 2σ(F 2)] = 0.036
wR(F 2) = 0.092
S = 1.05
3569 reflections
110 parameters
H-atom parameters constrained
Δρmax = 1.32 e Å−3
Δρmin = −1.22 e Å−3
Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXL97.
Supplementary Material
Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813031814/xu5753sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813031814/xu5753Isup2.hkl
Additional supplementary materials: crystallographic information; 3D view; checkCIF report
Table 1. Selected bond lengths (Å).
| Ag—N1 | 2.1373 (19) |
| Ag—N2i | 2.1654 (19) |
Symmetry code: (i) 
.
Acknowledgments
We are grateful to the Taoyuan Innovation Institute of Technology and the National Science Council of Taiwan for support.
supplementary crystallographic information
0.1. Synthesis and crystallization
An aqueous solution (5.0 ml) of AgNO3 (1.0 mmol) was layered carefully over a methanolic solution (5.0 ml) of N-(pyridin-2-yl)methansulfonamide (1.0 mmol) in a tube and kept it in the dark. Colourless crystals were obtained after several weeks. These were washed with methanol and collected in 78.6% yield.
0.2. Refinement
H atoms were placed in idealized positions and constrained to ride on their parent atoms with C—H = 0.93 or 0.96 Å, Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C) for the others.
1. Results and discussion
A series of complexes with the symmetric di(pyridyl/pyrimidyl)amide ligands (Hu et al., 2004; Hsu et al., 2008; Yeh et al., 2008; Tsai et al., 2010) and the asymmetric methyl-4-(pyridin-/pyrimidin-2-ylcarbamoyl)benzoate (Wu et al., 2011; Hsiao et al., 2012) or phosphinic amide (Yeh & Chen, 2011; Yeh et al., 2012) ligands that exhibit interesting structural types have been synthesized and structurally characterized. These pyridyl/pyrimidyl amide ligands coordinate to the metal centers through their pyridyl/pyrimidyl nitrogen atoms and/or amide oxygen atoms and interact with each other through hydrogen bonds involving the amide groups. These interactions are important for molecular recognition and constructing supramolecular arrays. .
In the title compound, [Ag(C6H7N2SO2)]2, the Ag+ cations are coordinated with one pyridyl N and one amido N atoms from twoN-(pyridin-2-yl)methanesulfonamido (L-) anions forming a slightly bent geometry (Fig. 1). The Ag···Ag distance separated by the bridging L- group is 2.7072 (4) Å.
Figures
Fig. 1.
Crystal structure of the title compound with labeling and displacement ellipsoids drawn at 30% probability level. [Symmetry codes: (i) -x,-y + 1,-z + 1.]
Crystal data
| [Ag2(C6H7N2O2S)2] | F(000) = 544 |
| Mr = 558.13 | Dx = 2.323 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 6474 reflections |
| a = 6.4406 (2) Å | θ = 2.6–35.3° |
| b = 15.4580 (5) Å | µ = 2.74 mm−1 |
| c = 8.0789 (2) Å | T = 296 K |
| β = 97.143 (2)° | Column, colourless |
| V = 798.08 (4) Å3 | 0.20 × 0.10 × 0.10 mm |
| Z = 2 |
Data collection
| Bruker APEXII CCD area-detector diffractometer | 3569 independent reflections |
| Radiation source: fine-focus sealed tube | 2732 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.048 |
| phi and ω scans | θmax = 35.4°, θmin = 2.6° |
| Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −10→8 |
| Tmin = 0.636, Tmax = 0.747 | k = −25→22 |
| 12917 measured reflections | l = −13→11 |
Refinement
| 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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.092 | H-atom parameters constrained |
| S = 1.05 | w = 1/[σ2(Fo2) + (0.0368P)2 + 0.3136P] where P = (Fo2 + 2Fc2)/3 |
| 3569 reflections | (Δ/σ)max = 0.001 |
| 110 parameters | Δρmax = 1.32 e Å−3 |
| 0 restraints | Δρmin = −1.22 e Å−3 |
Special details
| 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 > σ(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)
| x | y | z | Uiso*/Ueq | ||
| Ag | 0.13566 (3) | 0.475803 (15) | 0.63351 (2) | 0.03999 (8) | |
| S | 0.07511 (10) | 0.64837 (4) | 0.14689 (7) | 0.02803 (12) | |
| C1 | 0.5244 (4) | 0.58574 (16) | 0.6741 (3) | 0.0306 (4) | |
| H1A | 0.5410 | 0.5553 | 0.7742 | 0.037* | |
| C2 | 0.6811 (4) | 0.64120 (18) | 0.6425 (3) | 0.0354 (5) | |
| H2A | 0.8011 | 0.6483 | 0.7181 | 0.043* | |
| C3 | 0.6530 (4) | 0.68622 (16) | 0.4931 (3) | 0.0357 (5) | |
| H3A | 0.7560 | 0.7241 | 0.4664 | 0.043* | |
| C4 | 0.4738 (4) | 0.67511 (16) | 0.3846 (3) | 0.0318 (5) | |
| H4A | 0.4547 | 0.7060 | 0.2851 | 0.038* | |
| C5 | 0.3186 (3) | 0.61698 (14) | 0.4237 (3) | 0.0245 (4) | |
| C6 | 0.2438 (5) | 0.6112 (2) | 0.0057 (3) | 0.0422 (6) | |
| H6A | 0.2090 | 0.6393 | −0.1001 | 0.063* | |
| H6B | 0.2281 | 0.5498 | −0.0083 | 0.063* | |
| H6C | 0.3860 | 0.6243 | 0.0487 | 0.063* | |
| N1 | 0.3482 (3) | 0.57273 (12) | 0.5690 (2) | 0.0255 (3) | |
| N2 | 0.1362 (3) | 0.59867 (13) | 0.3207 (2) | 0.0274 (4) | |
| O1 | −0.1324 (3) | 0.61682 (13) | 0.0849 (2) | 0.0406 (4) | |
| O2 | 0.1003 (3) | 0.74049 (12) | 0.1604 (3) | 0.0402 (4) |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Ag | 0.03197 (12) | 0.05057 (14) | 0.03650 (11) | −0.01463 (8) | 0.00059 (8) | 0.01295 (8) |
| S | 0.0278 (3) | 0.0277 (3) | 0.0283 (3) | 0.0004 (2) | 0.00232 (19) | 0.00570 (19) |
| C1 | 0.0274 (11) | 0.0352 (12) | 0.0286 (10) | −0.0003 (9) | 0.0011 (8) | −0.0004 (8) |
| C2 | 0.0271 (12) | 0.0397 (13) | 0.0381 (13) | −0.0043 (10) | −0.0016 (9) | −0.0069 (10) |
| C3 | 0.0319 (12) | 0.0328 (11) | 0.0426 (13) | −0.0105 (10) | 0.0054 (10) | −0.0031 (10) |
| C4 | 0.0300 (12) | 0.0317 (11) | 0.0337 (11) | −0.0076 (9) | 0.0040 (9) | 0.0033 (9) |
| C5 | 0.0227 (10) | 0.0246 (9) | 0.0267 (9) | −0.0013 (7) | 0.0047 (7) | −0.0011 (7) |
| C6 | 0.0492 (17) | 0.0462 (15) | 0.0330 (12) | −0.0013 (12) | 0.0125 (11) | −0.0002 (10) |
| N1 | 0.0251 (9) | 0.0272 (9) | 0.0245 (8) | −0.0005 (7) | 0.0041 (6) | 0.0009 (6) |
| N2 | 0.0242 (9) | 0.0306 (9) | 0.0272 (8) | −0.0035 (7) | 0.0017 (7) | 0.0060 (7) |
| O1 | 0.0325 (10) | 0.0472 (11) | 0.0388 (10) | −0.0050 (8) | −0.0082 (8) | 0.0109 (8) |
| O2 | 0.0416 (11) | 0.0275 (8) | 0.0506 (11) | 0.0033 (7) | 0.0028 (9) | 0.0078 (7) |
Geometric parameters (Å, º)
| Ag—N1 | 2.1373 (19) | C2—H2A | 0.9300 |
| Ag—N2i | 2.1654 (19) | C3—C4 | 1.370 (4) |
| Ag—Agi | 2.7072 (4) | C3—H3A | 0.9300 |
| S—O2 | 1.4359 (19) | C4—C5 | 1.409 (3) |
| S—O1 | 1.452 (2) | C4—H4A | 0.9300 |
| S—N2 | 1.6061 (19) | C5—N1 | 1.351 (3) |
| S—C6 | 1.766 (3) | C5—N2 | 1.382 (3) |
| C1—N1 | 1.345 (3) | C6—H6A | 0.9600 |
| C1—C2 | 1.372 (4) | C6—H6B | 0.9600 |
| C1—H1A | 0.9300 | C6—H6C | 0.9600 |
| C2—C3 | 1.385 (4) | N2—Agi | 2.1654 (19) |
| N1—Ag—N2i | 166.03 (7) | C3—C4—C5 | 120.1 (2) |
| N1—Ag—Agi | 88.95 (5) | C3—C4—H4A | 120.0 |
| N2i—Ag—Agi | 80.07 (5) | C5—C4—H4A | 120.0 |
| O2—S—O1 | 116.73 (12) | N1—C5—N2 | 115.93 (19) |
| O2—S—N2 | 113.24 (11) | N1—C5—C4 | 119.3 (2) |
| O1—S—N2 | 104.81 (11) | N2—C5—C4 | 124.7 (2) |
| O2—S—C6 | 107.40 (13) | S—C6—H6A | 109.5 |
| O1—S—C6 | 106.38 (14) | S—C6—H6B | 109.5 |
| N2—S—C6 | 107.79 (13) | H6A—C6—H6B | 109.5 |
| N1—C1—C2 | 123.9 (2) | S—C6—H6C | 109.5 |
| N1—C1—H1A | 118.0 | H6A—C6—H6C | 109.5 |
| C2—C1—H1A | 118.0 | H6B—C6—H6C | 109.5 |
| C1—C2—C3 | 117.2 (2) | C1—N1—C5 | 119.3 (2) |
| C1—C2—H2A | 121.4 | C1—N1—Ag | 117.82 (15) |
| C3—C2—H2A | 121.4 | C5—N1—Ag | 122.74 (15) |
| C4—C3—C2 | 120.2 (2) | C5—N2—S | 121.75 (15) |
| C4—C3—H3A | 119.9 | C5—N2—Agi | 130.60 (14) |
| C2—C3—H3A | 119.9 | S—N2—Agi | 106.75 (10) |
Symmetry code: (i) −x, −y+1, −z+1.
Footnotes
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5753).
References
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813031814/xu5753sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813031814/xu5753Isup2.hkl
Additional supplementary materials: crystallographic information; 3D view; checkCIF report