Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807041645/hb2517sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807041645/hb2517Isup2.hkl |
CCDC reference: 660176
Key indicators
- Single-crystal X-ray study
- T = 153 K
- Mean (C-C) = 0.006 Å
- R factor = 0.054
- wR factor = 0.132
- Data-to-parameter ratio = 15.5
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.90
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.899 Tmax scaled 0.899 Tmin scaled 0.580 PLAT794_ALERT_5_G Check Predicted Bond Valency for Ag1 (9) 0.82 PLAT794_ALERT_5_G Check Predicted Bond Valency for Ag2 (9) 0.86 PLAT804_ALERT_5_G ARU-Pack Problem in PLATON Analysis ............ 1 Times
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 3 ALERT type 5 Informative message, check
For related polymeric silver salts containing the 4-pyridinealdazine ligand, see: Shi et al. (2002); Patra & Goldberg (2003); Kennedy et al. (2005).
For related literature, see: Broker & Tiekink (2007a, 2007b).
Ag(CH3SO3) (Aldrich, 0.05 g, 0.25 mmol) was dissolved in CH3CN (20 ml) and layered on top of a CH2Cl2 solution (20 ml) containing 0.05 g (0.25 mmol) of 4-pyridinealdazine (Aldrich). After three days, yellow prisms of (I) were observed at the interface between the two layers; m. pt. 522 - 524 K.
All the H atoms were included in the riding-model approximation, with C–H = 0.95–0.98 Å, and with Uiso(H) = 1.2 or 1.5Ueq(methyl C). The maximum and minimum difference peaks are located 1.14 and 0.84 Å, respectively, from Ag1.
The polymeric title compound, [Ag(C12H10N4)]n.n(CH3SO3) or [Ag(4—PA)]n.n(CH3SO3), (I), was investigated as a part of an on-going study of the structural chemistry of Ag salts of isomeric n-pyridinealdazine molecules, n = 2, 3 and 4 (Broker & Tiekink, 2007a,b). The asymmetric unit of (I) comprises two Ag atoms, a 4-pyridinealdazine (4-PA) molecule in a general position, two 4-PA molecules each disposed about a centre of inversion, and two methanesulfonate anions (Fig. 1). All the 4-PA ligands are bidentate bridging, resulting in polymeric chains and linear N2 geometries for each Ag atom (Table 1). A small twist in the N—C—C—N portions of the bridging ligand occupying the general position [C6—N2—N3—C7 = 163.0 (4)°] dictates that the chain is not strictly flat. The linear chains are connected into supramolecular double chains via weak Ag1···Ag2 agentophilic interactions [Ag···Ag = 3.2088 (10) Å]. The double chains stack along the b axis being interspersed by anions to form a layer structure (Fig. 2). Connections between layers are afforded by Ag···O interactions with the most significant being Ag1···O1, O4i and O5i of 2.694 (4), 2.797 (4), and 2.770 (4) Å, respectively (i: 1 - x, -y, 1 - z), and Ag2···O4, O1ii and O3ii of 2.743 (4), 2.811 (4) and 2.993 (4) Å, respectively (ii: 1 - x, -y, 1 - z). A view of the unit-cell contents highlighting the stacking of layers is shown in Fig. 3.
Similar [Ag(4—PA)]n polymeric chains as seen for (I) are found in the following salts: perchlorate, tetrafluoroborate (as acetonitrile solvates, Kennedy et al., 2005), hexafluoroantimonate (as the acetonitrile water solvate, Kennedy et al., 2005), and nitrate, for which two polymorphs have been reported (Shi et al., 2002; Patra & Goldberg, 2003 & Kennedy et al., 2005). In all but the nitrate polymorphs, the chains are essentially flat. In none of the above compounds are Ag···Ag interactions found.
For related polymeric silver salts containing the 4-pyridinealdazine ligand, see: Shi et al. (2002); Patra & Goldberg (2003); Kennedy et al. (2005).
For related literature, see: Broker & Tiekink (2007a, 2007b).
Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
[Ag(C12H10N4)]CH3O3S | F(000) = 3296 |
Mr = 413.22 | Dx = 1.853 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71070 Å |
Hall symbol: -C 2yc | Cell parameters from 10582 reflections |
a = 25.083 (9) Å | θ = 1.9–25.0° |
b = 12.284 (4) Å | µ = 1.52 mm−1 |
c = 21.009 (7) Å | T = 153 K |
β = 113.790 (7)° | Prism, yellow |
V = 5923 (3) Å3 | 0.30 × 0.08 × 0.07 mm |
Z = 16 |
Rigaku AFC12κ/SATURN724 diffractometer | 6151 independent reflections |
Radiation source: fine-focus sealed tube | 5879 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.048 |
ω scans | θmax = 26.5°, θmin = 1.9° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −29→31 |
Tmin = 0.645, Tmax = 1.000 | k = −15→15 |
37758 measured reflections | l = −26→22 |
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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.132 | H-atom parameters constrained |
S = 1.16 | w = 1/[σ2(Fo2) + (0.056P)2 + 41.7048P] where P = (Fo2 + 2Fc2)/3 |
6151 reflections | (Δ/σ)max = 0.002 |
397 parameters | Δρmax = 1.98 e Å−3 |
0 restraints | Δρmin = −1.28 e Å−3 |
[Ag(C12H10N4)]CH3O3S | V = 5923 (3) Å3 |
Mr = 413.22 | Z = 16 |
Monoclinic, C2/c | Mo Kα radiation |
a = 25.083 (9) Å | µ = 1.52 mm−1 |
b = 12.284 (4) Å | T = 153 K |
c = 21.009 (7) Å | 0.30 × 0.08 × 0.07 mm |
β = 113.790 (7)° |
Rigaku AFC12κ/SATURN724 diffractometer | 6151 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 5879 reflections with I > 2σ(I) |
Tmin = 0.645, Tmax = 1.000 | Rint = 0.048 |
37758 measured reflections |
R[F2 > 2σ(F2)] = 0.054 | 0 restraints |
wR(F2) = 0.132 | H-atom parameters constrained |
S = 1.16 | w = 1/[σ2(Fo2) + (0.056P)2 + 41.7048P] where P = (Fo2 + 2Fc2)/3 |
6151 reflections | Δρmax = 1.98 e Å−3 |
397 parameters | Δρmin = −1.28 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
Ag1 | 0.264234 (14) | 0.11412 (3) | 0.115089 (16) | 0.02522 (12) | |
Ag2 | 0.761261 (15) | 0.13780 (3) | 0.867951 (17) | 0.02714 (12) | |
S1 | 0.14174 (4) | −0.00296 (9) | 0.18189 (5) | 0.0232 (2) | |
S2 | 0.63856 (4) | 0.00487 (9) | 0.93140 (5) | 0.0227 (2) | |
O1 | 0.17575 (14) | 0.0433 (3) | 0.14587 (17) | 0.0349 (8) | |
O2 | 0.15577 (14) | 0.0447 (3) | 0.24999 (17) | 0.0355 (8) | |
O3 | 0.14380 (15) | −0.1215 (3) | 0.1835 (2) | 0.0354 (8) | |
O4 | 0.66998 (14) | 0.0630 (3) | 0.89604 (16) | 0.0297 (7) | |
O5 | 0.64598 (14) | −0.1133 (3) | 0.92975 (17) | 0.0282 (7) | |
O6 | 0.65091 (14) | 0.0461 (3) | 1.00060 (16) | 0.0331 (8) | |
N1 | 0.32271 (16) | 0.1270 (3) | 0.2246 (2) | 0.0233 (8) | |
N2 | 0.49505 (16) | 0.1637 (3) | 0.45649 (18) | 0.0272 (8) | |
N3 | 0.52542 (16) | 0.1634 (4) | 0.52935 (19) | 0.0273 (8) | |
N4 | 0.70009 (16) | 0.1535 (3) | 0.76056 (19) | 0.0225 (8) | |
N5 | 0.19914 (16) | 0.1277 (3) | 0.00882 (19) | 0.0233 (8) | |
N6 | 0.01700 (17) | 0.1235 (3) | −0.21380 (19) | 0.0281 (9) | |
N7 | 0.81773 (16) | 0.1530 (3) | 0.97678 (19) | 0.0225 (8) | |
N8 | 0.98552 (16) | 0.1972 (3) | 1.21342 (18) | 0.0269 (8) | |
C1 | 0.38045 (19) | 0.1436 (4) | 0.2423 (2) | 0.0235 (9) | |
H1 | 0.3938 | 0.1523 | 0.2062 | 0.028* | |
C2 | 0.42060 (19) | 0.1483 (4) | 0.3104 (2) | 0.0243 (9) | |
H2 | 0.4606 | 0.1615 | 0.3208 | 0.029* | |
C3 | 0.40169 (19) | 0.1335 (4) | 0.3639 (2) | 0.0229 (9) | |
C4 | 0.34180 (19) | 0.1144 (4) | 0.3451 (2) | 0.0235 (9) | |
H4 | 0.3274 | 0.1026 | 0.3800 | 0.028* | |
C5 | 0.30417 (19) | 0.1131 (4) | 0.2757 (2) | 0.0224 (9) | |
H5 | 0.2638 | 0.1018 | 0.2637 | 0.027* | |
C6 | 0.4412 (2) | 0.1367 (4) | 0.4377 (2) | 0.0249 (9) | |
H6 | 0.4269 | 0.1187 | 0.4720 | 0.030* | |
C7 | 0.58074 (19) | 0.1619 (4) | 0.5471 (2) | 0.0232 (9) | |
H7 | 0.5959 | 0.1612 | 0.5124 | 0.028* | |
C8 | 0.62066 (18) | 0.1611 (4) | 0.6211 (2) | 0.0224 (9) | |
C9 | 0.68083 (19) | 0.1661 (4) | 0.6398 (2) | 0.0250 (9) | |
H9 | 0.6955 | 0.1719 | 0.6048 | 0.030* | |
C10 | 0.71890 (19) | 0.1625 (4) | 0.7088 (2) | 0.0252 (9) | |
H10 | 0.7596 | 0.1664 | 0.7204 | 0.030* | |
C11 | 0.64189 (19) | 0.1490 (4) | 0.7429 (2) | 0.0244 (9) | |
H11 | 0.6283 | 0.1422 | 0.7789 | 0.029* | |
C12 | 0.60160 (19) | 0.1539 (4) | 0.6752 (2) | 0.0240 (9) | |
H12 | 0.5611 | 0.1525 | 0.6651 | 0.029* | |
C13 | 0.1417 (2) | 0.1261 (4) | −0.0053 (2) | 0.0247 (9) | |
H13 | 0.1302 | 0.1240 | 0.0327 | 0.030* | |
C14 | 0.0987 (2) | 0.1274 (4) | −0.0716 (2) | 0.0248 (9) | |
H14 | 0.0588 | 0.1280 | −0.0790 | 0.030* | |
C15 | 0.11503 (19) | 0.1277 (4) | −0.1282 (2) | 0.0224 (9) | |
C16 | 0.1747 (2) | 0.1291 (4) | −0.1137 (2) | 0.0252 (9) | |
H16 | 0.1873 | 0.1296 | −0.1507 | 0.030* | |
C17 | 0.2149 (2) | 0.1297 (4) | −0.0456 (2) | 0.0249 (9) | |
H17 | 0.2551 | 0.1316 | −0.0365 | 0.030* | |
C18 | 0.0717 (2) | 0.1261 (4) | −0.2006 (2) | 0.0245 (9) | |
H18 | 0.0842 | 0.1271 | −0.2377 | 0.029* | |
C19 | 0.87543 (19) | 0.1692 (4) | 0.9965 (2) | 0.0255 (9) | |
H19 | 0.8900 | 0.1758 | 0.9614 | 0.031* | |
C20 | 0.91447 (19) | 0.1767 (4) | 1.0653 (2) | 0.0252 (9) | |
H20 | 0.9547 | 0.1892 | 1.0768 | 0.030* | |
C21 | 0.89386 (19) | 0.1656 (4) | 1.1176 (2) | 0.0226 (9) | |
C22 | 0.83412 (19) | 0.1478 (4) | 1.0970 (2) | 0.0235 (9) | |
H22 | 0.8186 | 0.1389 | 1.1311 | 0.028* | |
C23 | 0.7977 (2) | 0.1432 (4) | 1.0272 (2) | 0.0245 (9) | |
H23 | 0.7572 | 0.1326 | 1.0142 | 0.029* | |
C24 | 0.93200 (19) | 0.1704 (4) | 1.1924 (2) | 0.0245 (9) | |
H24 | 0.9164 | 0.1531 | 1.2255 | 0.029* | |
C25 | 0.06786 (19) | 0.0330 (4) | 0.1304 (3) | 0.0315 (10) | |
H25A | 0.0561 | 0.0026 | 0.0836 | 0.047* | |
H25B | 0.0642 | 0.1125 | 0.1275 | 0.047* | |
H25C | 0.0427 | 0.0038 | 0.1519 | 0.047* | |
C26 | 0.56288 (19) | 0.0300 (4) | 0.8806 (2) | 0.0279 (10) | |
H26A | 0.5524 | 0.0033 | 0.8331 | 0.042* | |
H26B | 0.5553 | 0.1084 | 0.8794 | 0.042* | |
H26C | 0.5395 | −0.0080 | 0.9014 | 0.042* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ag1 | 0.01883 (19) | 0.0370 (2) | 0.01557 (19) | 0.00061 (13) | 0.00254 (14) | −0.00006 (13) |
Ag2 | 0.02145 (19) | 0.0376 (2) | 0.01613 (19) | −0.00067 (13) | 0.00110 (14) | −0.00008 (13) |
S1 | 0.0180 (5) | 0.0310 (6) | 0.0190 (5) | 0.0005 (4) | 0.0058 (4) | 0.0016 (4) |
S2 | 0.0180 (5) | 0.0311 (6) | 0.0183 (5) | 0.0000 (4) | 0.0065 (4) | −0.0001 (4) |
O1 | 0.0228 (16) | 0.057 (2) | 0.0242 (17) | −0.0014 (15) | 0.0087 (14) | 0.0060 (15) |
O2 | 0.0267 (17) | 0.055 (2) | 0.0223 (17) | 0.0054 (16) | 0.0080 (14) | −0.0057 (15) |
O3 | 0.0268 (18) | 0.0336 (19) | 0.041 (2) | 0.0013 (14) | 0.0085 (16) | 0.0017 (15) |
O4 | 0.0237 (16) | 0.042 (2) | 0.0261 (16) | −0.0039 (14) | 0.0127 (13) | 0.0020 (14) |
O5 | 0.0231 (17) | 0.0316 (18) | 0.0289 (18) | 0.0043 (13) | 0.0095 (14) | 0.0021 (13) |
O6 | 0.0284 (17) | 0.049 (2) | 0.0205 (16) | 0.0024 (15) | 0.0085 (14) | −0.0059 (15) |
N1 | 0.0173 (18) | 0.031 (2) | 0.0176 (18) | 0.0006 (14) | 0.0026 (15) | 0.0001 (14) |
N2 | 0.0226 (19) | 0.042 (2) | 0.0131 (17) | −0.0025 (17) | 0.0034 (15) | −0.0013 (16) |
N3 | 0.0197 (18) | 0.045 (2) | 0.0129 (17) | 0.0008 (17) | 0.0016 (14) | 0.0024 (16) |
N4 | 0.0171 (18) | 0.031 (2) | 0.0158 (17) | 0.0006 (14) | 0.0029 (14) | 0.0006 (14) |
N5 | 0.0169 (18) | 0.033 (2) | 0.0168 (18) | −0.0014 (14) | 0.0037 (15) | 0.0019 (14) |
N6 | 0.0200 (19) | 0.042 (2) | 0.016 (2) | 0.0003 (16) | 0.0012 (16) | 0.0014 (15) |
N7 | 0.0176 (18) | 0.031 (2) | 0.0143 (17) | −0.0007 (14) | 0.0012 (14) | 0.0000 (14) |
N8 | 0.0243 (19) | 0.036 (2) | 0.0162 (19) | −0.0017 (16) | 0.0040 (15) | −0.0003 (15) |
C1 | 0.019 (2) | 0.029 (2) | 0.024 (2) | −0.0011 (17) | 0.0101 (18) | −0.0002 (17) |
C2 | 0.018 (2) | 0.032 (2) | 0.022 (2) | 0.0017 (17) | 0.0082 (18) | 0.0025 (18) |
C3 | 0.019 (2) | 0.029 (2) | 0.018 (2) | 0.0004 (16) | 0.0034 (17) | 0.0014 (16) |
C4 | 0.020 (2) | 0.030 (2) | 0.021 (2) | 0.0011 (17) | 0.0086 (18) | 0.0002 (17) |
C5 | 0.017 (2) | 0.027 (2) | 0.022 (2) | −0.0008 (16) | 0.0062 (17) | −0.0011 (17) |
C6 | 0.022 (2) | 0.037 (3) | 0.014 (2) | 0.0008 (18) | 0.0058 (17) | 0.0023 (17) |
C7 | 0.022 (2) | 0.028 (2) | 0.018 (2) | −0.0023 (17) | 0.0067 (17) | −0.0004 (17) |
C8 | 0.019 (2) | 0.025 (2) | 0.022 (2) | −0.0007 (16) | 0.0079 (17) | 0.0000 (17) |
C9 | 0.023 (2) | 0.032 (2) | 0.023 (2) | −0.0018 (18) | 0.0121 (18) | 0.0025 (18) |
C10 | 0.020 (2) | 0.034 (2) | 0.022 (2) | −0.0002 (18) | 0.0090 (18) | 0.0018 (18) |
C11 | 0.018 (2) | 0.035 (2) | 0.021 (2) | 0.0028 (17) | 0.0081 (18) | 0.0011 (18) |
C12 | 0.017 (2) | 0.034 (2) | 0.020 (2) | 0.0010 (17) | 0.0073 (17) | 0.0006 (18) |
C13 | 0.023 (2) | 0.031 (2) | 0.021 (2) | 0.0032 (17) | 0.0100 (19) | 0.0025 (17) |
C14 | 0.018 (2) | 0.031 (2) | 0.027 (2) | 0.0007 (17) | 0.0101 (18) | 0.0029 (18) |
C15 | 0.019 (2) | 0.027 (2) | 0.017 (2) | −0.0004 (16) | 0.0027 (17) | 0.0005 (16) |
C16 | 0.022 (2) | 0.031 (2) | 0.024 (2) | −0.0003 (17) | 0.0107 (19) | 0.0021 (18) |
C17 | 0.021 (2) | 0.030 (2) | 0.025 (2) | −0.0002 (17) | 0.0108 (19) | 0.0012 (17) |
C18 | 0.023 (2) | 0.028 (2) | 0.020 (2) | −0.0009 (17) | 0.0070 (18) | 0.0002 (17) |
C19 | 0.023 (2) | 0.032 (2) | 0.021 (2) | −0.0026 (18) | 0.0087 (18) | 0.0023 (18) |
C20 | 0.017 (2) | 0.033 (2) | 0.023 (2) | −0.0027 (17) | 0.0047 (17) | 0.0000 (18) |
C21 | 0.020 (2) | 0.024 (2) | 0.022 (2) | −0.0012 (17) | 0.0064 (17) | 0.0012 (17) |
C22 | 0.019 (2) | 0.028 (2) | 0.024 (2) | −0.0006 (17) | 0.0100 (18) | 0.0010 (17) |
C23 | 0.021 (2) | 0.028 (2) | 0.024 (2) | −0.0007 (17) | 0.0093 (18) | −0.0011 (17) |
C24 | 0.026 (2) | 0.028 (2) | 0.017 (2) | 0.0024 (18) | 0.0063 (18) | 0.0034 (17) |
C25 | 0.021 (2) | 0.039 (3) | 0.030 (2) | 0.0001 (19) | 0.0064 (19) | 0.002 (2) |
C26 | 0.020 (2) | 0.033 (2) | 0.025 (2) | 0.0011 (18) | 0.0032 (18) | 0.0009 (19) |
Ag1—N1 | 2.179 (4) | C6—H6 | 0.9500 |
Ag1—N5 | 2.177 (4) | C7—C8 | 1.471 (6) |
Ag2—N4 | 2.165 (4) | C7—H7 | 0.9500 |
Ag2—N7 | 2.158 (4) | C8—C9 | 1.399 (6) |
Ag1—Ag2i | 3.2088 (10) | C8—C12 | 1.402 (6) |
Ag2—Ag1i | 3.2088 (10) | C9—C10 | 1.378 (6) |
S1—O2 | 1.452 (3) | C9—H9 | 0.9500 |
S1—O3 | 1.457 (4) | C10—H10 | 0.9500 |
S1—O1 | 1.464 (3) | C11—C12 | 1.375 (6) |
S1—C25 | 1.784 (5) | C11—H11 | 0.9500 |
S2—O6 | 1.450 (3) | C12—H12 | 0.9500 |
S2—O5 | 1.466 (3) | C13—C14 | 1.375 (7) |
S2—O4 | 1.468 (3) | C13—H13 | 0.9500 |
S2—C26 | 1.790 (4) | C14—C15 | 1.404 (6) |
N1—C5 | 1.341 (6) | C14—H14 | 0.9500 |
N1—C1 | 1.358 (6) | C15—C16 | 1.401 (6) |
N2—C6 | 1.289 (6) | C15—C18 | 1.470 (6) |
N2—N3 | 1.408 (5) | C16—C17 | 1.379 (7) |
N3—C7 | 1.283 (6) | C16—H16 | 0.9500 |
N4—C10 | 1.352 (6) | C17—H17 | 0.9500 |
N4—C11 | 1.355 (6) | C18—H18 | 0.9500 |
N5—C13 | 1.350 (6) | C19—C20 | 1.384 (6) |
N5—C17 | 1.351 (6) | C19—H19 | 0.9500 |
N6—C18 | 1.286 (6) | C20—C21 | 1.397 (6) |
N6—N6ii | 1.412 (7) | C20—H20 | 0.9500 |
N7—C23 | 1.347 (6) | C21—C22 | 1.399 (6) |
N7—C19 | 1.350 (6) | C21—C24 | 1.474 (6) |
N8—C24 | 1.276 (6) | C22—C23 | 1.382 (6) |
N8—N8iii | 1.411 (7) | C22—H22 | 0.9500 |
C1—C2 | 1.379 (6) | C23—H23 | 0.9500 |
C1—H1 | 0.9500 | C24—H24 | 0.9500 |
C2—C3 | 1.397 (6) | C25—H25A | 0.9800 |
C2—H2 | 0.9500 | C25—H25B | 0.9800 |
C3—C4 | 1.410 (6) | C25—H25C | 0.9800 |
C3—C6 | 1.466 (6) | C26—H26A | 0.9800 |
C4—C5 | 1.381 (6) | C26—H26B | 0.9800 |
C4—H4 | 0.9500 | C26—H26C | 0.9800 |
C5—H5 | 0.9500 | ||
N1—Ag1—N5 | 169.88 (15) | C10—C9—H9 | 119.8 |
N5—Ag1—Ag2i | 95.02 (10) | C8—C9—H9 | 119.8 |
N1—Ag1—Ag2i | 91.85 (10) | N4—C10—C9 | 122.0 (4) |
N4—Ag2—N7 | 169.32 (15) | N4—C10—H10 | 119.0 |
N7—Ag2—Ag1i | 92.34 (10) | C9—C10—H10 | 119.0 |
N4—Ag2—Ag1i | 96.46 (10) | N4—C11—C12 | 122.8 (4) |
O2—S1—O3 | 112.8 (2) | N4—C11—H11 | 118.6 |
O2—S1—O1 | 113.1 (2) | C12—C11—H11 | 118.6 |
O3—S1—O1 | 112.2 (2) | C11—C12—C8 | 119.6 (4) |
O2—S1—C25 | 106.1 (2) | C11—C12—H12 | 120.2 |
O3—S1—C25 | 106.3 (2) | C8—C12—H12 | 120.2 |
O1—S1—C25 | 105.7 (2) | N5—C13—C14 | 123.6 (4) |
O6—S2—O5 | 113.1 (2) | N5—C13—H13 | 118.2 |
O6—S2—O4 | 113.3 (2) | C14—C13—H13 | 118.2 |
O5—S2—O4 | 111.8 (2) | C13—C14—C15 | 118.8 (4) |
O6—S2—C26 | 106.5 (2) | C13—C14—H14 | 120.6 |
O5—S2—C26 | 105.7 (2) | C15—C14—H14 | 120.6 |
O4—S2—C26 | 105.7 (2) | C16—C15—C14 | 117.8 (4) |
C5—N1—C1 | 118.5 (4) | C16—C15—C18 | 120.2 (4) |
C5—N1—Ag1 | 122.2 (3) | C14—C15—C18 | 122.0 (4) |
C1—N1—Ag1 | 119.2 (3) | C17—C16—C15 | 119.6 (4) |
C6—N2—N3 | 111.9 (4) | C17—C16—H16 | 120.2 |
C7—N3—N2 | 111.3 (4) | C15—C16—H16 | 120.2 |
C10—N4—C11 | 118.1 (4) | N5—C17—C16 | 122.5 (4) |
C10—N4—Ag2 | 120.9 (3) | N5—C17—H17 | 118.7 |
C11—N4—Ag2 | 120.9 (3) | C16—C17—H17 | 118.7 |
C13—N5—C17 | 117.7 (4) | N6—C18—C15 | 120.2 (4) |
C13—N5—Ag1 | 121.1 (3) | N6—C18—H18 | 119.9 |
C17—N5—Ag1 | 121.0 (3) | C15—C18—H18 | 119.9 |
C18—N6—N6ii | 111.2 (5) | N7—C19—C20 | 123.4 (4) |
C23—N7—C19 | 117.7 (4) | N7—C19—H19 | 118.3 |
C23—N7—Ag2 | 122.1 (3) | C20—C19—H19 | 118.3 |
C19—N7—Ag2 | 120.2 (3) | C19—C20—C21 | 119.0 (4) |
C24—N8—N8iii | 112.6 (4) | C19—C20—H20 | 120.5 |
N1—C1—C2 | 122.8 (4) | C21—C20—H20 | 120.5 |
N1—C1—H1 | 118.6 | C20—C21—C22 | 117.5 (4) |
C2—C1—H1 | 118.6 | C20—C21—C24 | 123.2 (4) |
C1—C2—C3 | 119.1 (4) | C22—C21—C24 | 119.3 (4) |
C1—C2—H2 | 120.5 | C23—C22—C21 | 120.1 (4) |
C3—C2—H2 | 120.5 | C23—C22—H22 | 120.0 |
C2—C3—C4 | 117.8 (4) | C21—C22—H22 | 120.0 |
C2—C3—C6 | 123.0 (4) | N7—C23—C22 | 122.3 (4) |
C4—C3—C6 | 119.3 (4) | N7—C23—H23 | 118.8 |
C5—C4—C3 | 119.6 (4) | C22—C23—H23 | 118.8 |
C5—C4—H4 | 120.2 | N8—C24—C21 | 121.3 (4) |
C3—C4—H4 | 120.2 | N8—C24—H24 | 119.4 |
N1—C5—C4 | 122.2 (4) | C21—C24—H24 | 119.4 |
N1—C5—H5 | 118.9 | S1—C25—H25A | 109.5 |
C4—C5—H5 | 118.9 | S1—C25—H25B | 109.5 |
N2—C6—C3 | 120.5 (4) | H25A—C25—H25B | 109.5 |
N2—C6—H6 | 119.7 | S1—C25—H25C | 109.5 |
C3—C6—H6 | 119.7 | H25A—C25—H25C | 109.5 |
N3—C7—C8 | 120.2 (4) | H25B—C25—H25C | 109.5 |
N3—C7—H7 | 119.9 | S2—C26—H26A | 109.5 |
C8—C7—H7 | 119.9 | S2—C26—H26B | 109.5 |
C9—C8—C12 | 117.2 (4) | H26A—C26—H26B | 109.5 |
C9—C8—C7 | 119.6 (4) | S2—C26—H26C | 109.5 |
C12—C8—C7 | 123.2 (4) | H26A—C26—H26C | 109.5 |
C10—C9—C8 | 120.4 (4) | H26B—C26—H26C | 109.5 |
N5—Ag1—N1—C5 | 69.3 (9) | C11—N4—C10—C9 | −0.6 (7) |
Ag2i—Ag1—N1—C5 | −63.4 (3) | Ag2—N4—C10—C9 | 176.1 (4) |
N5—Ag1—N1—C1 | −114.5 (8) | C8—C9—C10—N4 | 0.4 (7) |
Ag2i—Ag1—N1—C1 | 112.7 (3) | C10—N4—C11—C12 | −0.4 (7) |
C6—N2—N3—C7 | 163.0 (4) | Ag2—N4—C11—C12 | −177.1 (4) |
N7—Ag2—N4—C10 | 106.9 (8) | N4—C11—C12—C8 | 1.7 (7) |
Ag1i—Ag2—N4—C10 | −107.7 (3) | C9—C8—C12—C11 | −1.8 (7) |
N7—Ag2—N4—C11 | −76.5 (9) | C7—C8—C12—C11 | 177.2 (4) |
Ag1i—Ag2—N4—C11 | 68.8 (3) | C17—N5—C13—C14 | −0.6 (7) |
N1—Ag1—N5—C13 | −61.5 (9) | Ag1—N5—C13—C14 | −175.7 (3) |
Ag2i—Ag1—N5—C13 | 71.0 (3) | N5—C13—C14—C15 | 1.6 (7) |
N1—Ag1—N5—C17 | 123.6 (8) | C13—C14—C15—C16 | −1.3 (7) |
Ag2i—Ag1—N5—C17 | −103.9 (3) | C13—C14—C15—C18 | 178.4 (4) |
N4—Ag2—N7—C23 | 79.9 (9) | C14—C15—C16—C17 | 0.2 (7) |
Ag1i—Ag2—N7—C23 | −65.6 (3) | C18—C15—C16—C17 | −179.5 (4) |
N4—Ag2—N7—C19 | −102.4 (8) | C13—N5—C17—C16 | −0.6 (7) |
Ag1i—Ag2—N7—C19 | 112.1 (3) | Ag1—N5—C17—C16 | 174.4 (3) |
C5—N1—C1—C2 | −1.0 (7) | C15—C16—C17—N5 | 0.8 (7) |
Ag1—N1—C1—C2 | −177.3 (3) | N6ii—N6—C18—C15 | 179.4 (3) |
N1—C1—C2—C3 | 1.2 (7) | C16—C15—C18—N6 | 179.1 (4) |
C1—C2—C3—C4 | −0.1 (7) | C14—C15—C18—N6 | −0.6 (7) |
C1—C2—C3—C6 | 179.8 (4) | C23—N7—C19—C20 | −0.4 (7) |
C2—C3—C4—C5 | −1.2 (6) | Ag2—N7—C19—C20 | −178.1 (4) |
C6—C3—C4—C5 | 179.0 (4) | N7—C19—C20—C21 | 0.9 (7) |
C1—N1—C5—C4 | −0.4 (6) | C19—C20—C21—C22 | −0.2 (7) |
Ag1—N1—C5—C4 | 175.8 (3) | C19—C20—C21—C24 | 178.9 (4) |
C3—C4—C5—N1 | 1.4 (7) | C20—C21—C22—C23 | −0.8 (7) |
N3—N2—C6—C3 | 179.1 (4) | C24—C21—C22—C23 | −180.0 (4) |
C2—C3—C6—N2 | 6.5 (7) | C19—N7—C23—C22 | −0.8 (7) |
C4—C3—C6—N2 | −173.6 (4) | Ag2—N7—C23—C22 | 177.0 (3) |
N2—N3—C7—C8 | −179.9 (4) | C21—C22—C23—N7 | 1.4 (7) |
N3—C7—C8—C9 | −176.2 (4) | N8iii—N8—C24—C21 | 179.8 (3) |
N3—C7—C8—C12 | 4.8 (7) | C20—C21—C24—N8 | 8.0 (7) |
C12—C8—C9—C10 | 0.8 (7) | C22—C21—C24—N8 | −172.9 (4) |
C7—C8—C9—C10 | −178.3 (4) |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x, y, −z−1/2; (iii) −x+2, y, −z+5/2. |
Experimental details
Crystal data | |
Chemical formula | [Ag(C12H10N4)]CH3O3S |
Mr | 413.22 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 153 |
a, b, c (Å) | 25.083 (9), 12.284 (4), 21.009 (7) |
β (°) | 113.790 (7) |
V (Å3) | 5923 (3) |
Z | 16 |
Radiation type | Mo Kα |
µ (mm−1) | 1.52 |
Crystal size (mm) | 0.30 × 0.08 × 0.07 |
Data collection | |
Diffractometer | Rigaku AFC12κ/SATURN724 |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.645, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 37758, 6151, 5879 |
Rint | 0.048 |
(sin θ/λ)max (Å−1) | 0.628 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.054, 0.132, 1.16 |
No. of reflections | 6151 |
No. of parameters | 397 |
H-atom treatment | H-atom parameters constrained |
w = 1/[σ2(Fo2) + (0.056P)2 + 41.7048P] where P = (Fo2 + 2Fc2)/3 | |
Δρmax, Δρmin (e Å−3) | 1.98, −1.28 |
Computer programs: CrystalClear (Rigaku/MSC, 2005), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976) and DIAMOND (Brandenburg, 2006).
Ag1—N1 | 2.179 (4) | Ag2—N7 | 2.158 (4) |
Ag1—N5 | 2.177 (4) | Ag1—Ag2i | 3.2088 (10) |
Ag2—N4 | 2.165 (4) | ||
N1—Ag1—N5 | 169.88 (15) | N4—Ag2—N7 | 169.32 (15) |
Symmetry code: (i) −x+1, −y, −z+1. |
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The polymeric title compound, [Ag(C12H10N4)]n.n(CH3SO3) or [Ag(4—PA)]n.n(CH3SO3), (I), was investigated as a part of an on-going study of the structural chemistry of Ag salts of isomeric n-pyridinealdazine molecules, n = 2, 3 and 4 (Broker & Tiekink, 2007a,b). The asymmetric unit of (I) comprises two Ag atoms, a 4-pyridinealdazine (4-PA) molecule in a general position, two 4-PA molecules each disposed about a centre of inversion, and two methanesulfonate anions (Fig. 1). All the 4-PA ligands are bidentate bridging, resulting in polymeric chains and linear N2 geometries for each Ag atom (Table 1). A small twist in the N—C—C—N portions of the bridging ligand occupying the general position [C6—N2—N3—C7 = 163.0 (4)°] dictates that the chain is not strictly flat. The linear chains are connected into supramolecular double chains via weak Ag1···Ag2 agentophilic interactions [Ag···Ag = 3.2088 (10) Å]. The double chains stack along the b axis being interspersed by anions to form a layer structure (Fig. 2). Connections between layers are afforded by Ag···O interactions with the most significant being Ag1···O1, O4i and O5i of 2.694 (4), 2.797 (4), and 2.770 (4) Å, respectively (i: 1 - x, -y, 1 - z), and Ag2···O4, O1ii and O3ii of 2.743 (4), 2.811 (4) and 2.993 (4) Å, respectively (ii: 1 - x, -y, 1 - z). A view of the unit-cell contents highlighting the stacking of layers is shown in Fig. 3.
Similar [Ag(4—PA)]n polymeric chains as seen for (I) are found in the following salts: perchlorate, tetrafluoroborate (as acetonitrile solvates, Kennedy et al., 2005), hexafluoroantimonate (as the acetonitrile water solvate, Kennedy et al., 2005), and nitrate, for which two polymorphs have been reported (Shi et al., 2002; Patra & Goldberg, 2003 & Kennedy et al., 2005). In all but the nitrate polymorphs, the chains are essentially flat. In none of the above compounds are Ag···Ag interactions found.