In the title compound, [Ag(NO3)(C15H18N6)], the AgI atom is four-coordinated by the three N atoms of the 2-aminopyridine ligands and by an O atom of the nitro group. The structure is stabilized by an extensive network of N—H—O and N—H—N hydrogen bonds.
Supporting information
CCDC reference: 650606
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.008 Å
- R factor = 0.028
- wR factor = 0.067
- Data-to-parameter ratio = 12.6
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H8B .. N21 .. 2.75 Ang.
Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
1 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
1 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
0 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: CrystalClear (Rigaku, 2004); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.
Tris(2-aminopyridine-
κN1)(nitrato-
κO)silver(I)
top
Crystal data top
[Ag(NO3)(C15H18N6)] | F(000) = 912 |
Mr = 452.23 | Dx = 1.824 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4551 reflections |
a = 10.932 (3) Å | θ = 2.2–28.0° |
b = 8.027 (2) Å | µ = 1.26 mm−1 |
c = 18.948 (6) Å | T = 293 K |
β = 98.001 (6)° | Needle, pale yellow |
V = 1646.4 (8) Å3 | 0.06 × 0.06 × 0.06 mm |
Z = 4 | |
Data collection top
CCD diffractometer | 2755 reflections with I > 2σ(I) |
dtprofit.ref scans | Rint = 0.055 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | θmax = 25.4°, θmin = 1.9° |
Tmin = 0.925, Tmax = 0.927 | h = −12→13 |
15950 measured reflections | k = −9→8 |
2981 independent reflections | l = −22→22 |
Refinement top
Refinement on F2 | 6 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.028 | w = 1/[σ2(Fo2) + (0.0279P)2 + 1.8285P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.067 | (Δ/σ)max = 0.001 |
S = 1.04 | Δρmax = 0.49 e Å−3 |
2981 reflections | Δρmin = −0.59 e Å−3 |
236 parameters | |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C2 | 0.4103 (5) | 0.4811 (6) | 0.8183 (3) | 0.0189 (11) | |
C3 | 0.4705 (5) | 0.5863 (7) | 0.7771 (3) | 0.0237 (12) | |
H3A | 0.5367 | 0.6505 | 0.7979 | 0.028* | |
C4 | 0.4318 (6) | 0.5957 (7) | 0.7050 (3) | 0.0269 (13) | |
H4A | 0.4724 | 0.6664 | 0.677 | 0.032* | |
C5 | 0.3342 (6) | 0.5023 (7) | 0.6739 (3) | 0.0279 (13) | |
H5A | 0.3075 | 0.5066 | 0.6252 | 0.034* | |
C6 | 0.2790 (5) | 0.4042 (7) | 0.7174 (3) | 0.0232 (12) | |
H6A | 0.2116 | 0.3411 | 0.6974 | 0.028* | |
C8 | −0.0662 (5) | 0.4027 (6) | 0.8429 (3) | 0.0196 (11) | |
C9 | −0.1852 (5) | 0.4490 (7) | 0.8113 (3) | 0.0210 (12) | |
H9A | −0.2296 | 0.527 | 0.8336 | 0.025* | |
C10 | −0.2360 (5) | 0.3810 (7) | 0.7484 (3) | 0.0238 (12) | |
H10A | −0.3142 | 0.4132 | 0.727 | 0.029* | |
C11 | −0.1704 (6) | 0.2647 (7) | 0.7172 (3) | 0.0236 (13) | |
H11A | −0.2022 | 0.2149 | 0.6742 | 0.028* | |
C12 | −0.0564 (5) | 0.2242 (7) | 0.7514 (3) | 0.0229 (12) | |
H12A | −0.012 | 0.1443 | 0.7302 | 0.028* | |
C14 | 0.1379 (5) | −0.0634 (6) | 0.9395 (3) | 0.0177 (11) | |
C15 | 0.1559 (5) | −0.1925 (7) | 0.9865 (3) | 0.0230 (12) | |
H15A | 0.0892 | −0.244 | 1.003 | 0.028* | |
C16 | 0.2734 (6) | −0.2448 (7) | 1.0086 (3) | 0.0270 (14) | |
H16A | 0.2868 | −0.3323 | 1.0409 | 0.032* | |
C17 | 0.3723 (6) | −0.1703 (7) | 0.9841 (3) | 0.0274 (13) | |
H17A | 0.4527 | −0.2069 | 0.9983 | 0.033* | |
C18 | 0.3486 (5) | −0.0443 (7) | 0.9394 (3) | 0.0233 (12) | |
H18A | 0.4146 | 0.0081 | 0.9225 | 0.028* | |
N1 | 0.3154 (4) | 0.3911 (5) | 0.7887 (2) | 0.0185 (10) | |
N2 | 0.4485 (4) | 0.4636 (6) | 0.8897 (2) | 0.0248 (11) | |
H2A | 0.411 | 0.3953 | 0.9143 | 0.03* | |
H2B | 0.5099 | 0.5209 | 0.91 | 0.03* | |
N7 | −0.0026 (4) | 0.2902 (5) | 0.8135 (2) | 0.0198 (10) | |
N8 | −0.0125 (4) | 0.4688 (6) | 0.9045 (2) | 0.0249 (11) | |
H8A | 0.0602 | 0.4369 | 0.9226 | 0.03* | |
H8B | −0.0507 | 0.5431 | 0.9258 | 0.03* | |
N13 | 0.2339 (4) | 0.0119 (5) | 0.9170 (2) | 0.0176 (9) | |
N14 | 0.0226 (4) | −0.0130 (6) | 0.9148 (3) | 0.0262 (11) | |
H14A | 0.0112 | 0.0675 | 0.8847 | 0.031* | |
H14B | −0.0397 | −0.0612 | 0.9292 | 0.031* | |
N21 | 0.2536 (4) | 0.3115 (5) | 1.0291 (2) | 0.0184 (9) | |
O21 | 0.2414 (4) | 0.3896 (5) | 0.9721 (2) | 0.0254 (9) | |
O22 | 0.3573 (4) | 0.2890 (6) | 1.0621 (3) | 0.0400 (12) | |
O23 | 0.1601 (4) | 0.2586 (5) | 1.0523 (2) | 0.0264 (9) | |
Ag1 | 0.21071 (4) | 0.22633 (5) | 0.84934 (2) | 0.02196 (19) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C2 | 0.016 (3) | 0.015 (3) | 0.027 (3) | 0.004 (2) | 0.004 (2) | −0.001 (2) |
C3 | 0.021 (3) | 0.017 (3) | 0.034 (3) | 0.000 (2) | 0.009 (2) | 0.001 (2) |
C4 | 0.035 (3) | 0.017 (3) | 0.033 (3) | 0.000 (2) | 0.017 (3) | 0.004 (2) |
C5 | 0.042 (4) | 0.020 (3) | 0.024 (3) | 0.000 (3) | 0.010 (3) | 0.001 (2) |
C6 | 0.030 (3) | 0.016 (3) | 0.023 (3) | 0.000 (2) | 0.003 (2) | 0.001 (2) |
C8 | 0.026 (3) | 0.011 (2) | 0.023 (3) | −0.002 (2) | 0.007 (2) | 0.004 (2) |
C9 | 0.021 (3) | 0.018 (3) | 0.025 (3) | 0.002 (2) | 0.006 (2) | 0.003 (2) |
C10 | 0.022 (3) | 0.022 (3) | 0.027 (3) | −0.002 (2) | 0.004 (2) | 0.008 (2) |
C11 | 0.030 (3) | 0.019 (3) | 0.022 (3) | −0.004 (2) | 0.004 (3) | 0.002 (2) |
C12 | 0.026 (3) | 0.019 (3) | 0.024 (3) | 0.001 (2) | 0.006 (3) | −0.002 (2) |
C14 | 0.022 (3) | 0.013 (3) | 0.019 (3) | −0.003 (2) | 0.003 (2) | −0.004 (2) |
C15 | 0.031 (3) | 0.014 (3) | 0.025 (3) | −0.005 (2) | 0.008 (2) | −0.002 (2) |
C16 | 0.041 (4) | 0.014 (3) | 0.024 (3) | 0.002 (2) | 0.000 (3) | −0.001 (2) |
C17 | 0.027 (3) | 0.025 (3) | 0.029 (3) | 0.007 (2) | −0.004 (3) | −0.005 (3) |
C18 | 0.021 (3) | 0.023 (3) | 0.026 (3) | −0.003 (2) | 0.003 (2) | −0.006 (2) |
N1 | 0.021 (2) | 0.011 (2) | 0.024 (2) | 0.0001 (18) | 0.0061 (19) | 0.0015 (18) |
N2 | 0.021 (3) | 0.026 (3) | 0.027 (3) | −0.006 (2) | −0.001 (2) | 0.005 (2) |
N7 | 0.021 (3) | 0.015 (2) | 0.023 (2) | 0.0011 (18) | 0.003 (2) | 0.0011 (18) |
N8 | 0.024 (3) | 0.022 (2) | 0.028 (3) | 0.0060 (19) | 0.000 (2) | −0.007 (2) |
N13 | 0.019 (2) | 0.014 (2) | 0.021 (2) | −0.0015 (18) | 0.0040 (19) | −0.0022 (18) |
N14 | 0.019 (3) | 0.024 (3) | 0.036 (3) | −0.002 (2) | 0.008 (2) | 0.009 (2) |
N21 | 0.020 (2) | 0.015 (2) | 0.021 (2) | −0.0028 (18) | 0.0030 (19) | −0.0049 (18) |
O21 | 0.035 (2) | 0.019 (2) | 0.022 (2) | −0.0031 (17) | 0.0028 (17) | 0.0023 (16) |
O22 | 0.021 (2) | 0.044 (3) | 0.050 (3) | −0.0072 (19) | −0.011 (2) | 0.016 (2) |
O23 | 0.022 (2) | 0.021 (2) | 0.039 (3) | −0.0044 (16) | 0.013 (2) | −0.0002 (17) |
Ag1 | 0.0261 (3) | 0.0173 (3) | 0.0235 (3) | −0.00416 (16) | 0.0068 (2) | 0.00111 (15) |
Geometric parameters (Å, º) top
C2—N1 | 1.323 (7) | C14—N14 | 1.344 (7) |
C2—N2 | 1.365 (7) | C14—C15 | 1.361 (8) |
C2—C3 | 1.378 (8) | C15—C16 | 1.361 (9) |
C3—C4 | 1.374 (8) | C15—H15A | 0.93 |
C3—H3A | 0.93 | C16—C17 | 1.373 (9) |
C4—C5 | 1.368 (8) | C16—H16A | 0.93 |
C4—H4A | 0.93 | C17—C18 | 1.321 (8) |
C5—C6 | 1.341 (8) | C17—H17A | 0.93 |
C5—H5A | 0.93 | C18—N13 | 1.345 (7) |
C6—N1 | 1.358 (7) | C18—H18A | 0.93 |
C6—H6A | 0.93 | N1—Ag1 | 2.179 (4) |
C8—N7 | 1.312 (7) | N2—H2A | 0.86 |
C8—N8 | 1.340 (7) | N2—H2B | 0.86 |
C8—C9 | 1.404 (8) | N7—Ag1 | 2.392 (5) |
C9—C10 | 1.358 (8) | N8—H8A | 0.86 |
C9—H9A | 0.93 | N8—H8B | 0.86 |
C10—C11 | 1.361 (8) | N13—Ag1 | 2.141 (4) |
C10—H10A | 0.93 | N14—H14A | 0.86 |
C11—C12 | 1.362 (8) | N14—H14B | 0.86 |
C11—H11A | 0.93 | N21—O22 | 1.229 (6) |
C12—N7 | 1.348 (7) | N21—O21 | 1.241 (6) |
C12—H12A | 0.93 | N21—O23 | 1.242 (6) |
C14—N13 | 1.332 (7) | O21—Ag1 | 2.649 (4) |
| | | |
N1—C2—N2 | 118.5 (5) | C15—C16—H16A | 119.5 |
N1—C2—C3 | 120.1 (5) | C17—C16—H16A | 119.5 |
N2—C2—C3 | 121.3 (5) | C18—C17—C16 | 117.2 (6) |
C4—C3—C2 | 119.5 (5) | C18—C17—H17A | 121.4 |
C4—C3—H3A | 120.3 | C16—C17—H17A | 121.4 |
C2—C3—H3A | 120.3 | C17—C18—N13 | 123.4 (5) |
C5—C4—C3 | 120.7 (5) | C17—C18—H18A | 118.3 |
C5—C4—H4A | 119.6 | N13—C18—H18A | 118.3 |
C3—C4—H4A | 119.6 | C2—N1—C6 | 118.9 (5) |
C6—C5—C4 | 116.6 (6) | C2—N1—Ag1 | 123.1 (4) |
C6—C5—H5A | 121.7 | C6—N1—Ag1 | 118.0 (4) |
C4—C5—H5A | 121.7 | C2—N2—H2A | 120 |
C5—C6—N1 | 124.1 (5) | C2—N2—H2B | 120 |
C5—C6—H6A | 117.9 | H2A—N2—H2B | 120 |
N1—C6—H6A | 117.9 | C8—N7—C12 | 116.7 (5) |
N7—C8—N8 | 116.7 (5) | C8—N7—Ag1 | 125.5 (4) |
N7—C8—C9 | 121.0 (5) | C12—N7—Ag1 | 117.0 (4) |
N8—C8—C9 | 122.4 (5) | C8—N8—H8A | 120 |
C10—C9—C8 | 120.7 (5) | C8—N8—H8B | 120 |
C10—C9—H9A | 119.7 | H8A—N8—H8B | 120 |
C8—C9—H9A | 119.7 | C14—N13—C18 | 119.3 (5) |
C9—C10—C11 | 118.7 (5) | C14—N13—Ag1 | 121.6 (3) |
C9—C10—H10A | 120.6 | C18—N13—Ag1 | 119.1 (4) |
C11—C10—H10A | 120.6 | C14—N14—H14A | 120 |
C10—C11—C12 | 117.4 (6) | C14—N14—H14B | 120 |
C10—C11—H11A | 121.3 | H14A—N14—H14B | 120 |
C12—C11—H11A | 121.3 | O22—N21—O21 | 119.8 (5) |
N7—C12—C11 | 125.5 (5) | O22—N21—O23 | 121.1 (5) |
N7—C12—H12A | 117.2 | O21—N21—O23 | 119.1 (5) |
C11—C12—H12A | 117.2 | N21—O21—Ag1 | 120.0 (3) |
N13—C14—N14 | 119.6 (5) | N13—Ag1—N1 | 141.02 (16) |
N13—C14—C15 | 120.4 (5) | N13—Ag1—N7 | 111.83 (16) |
N14—C14—C15 | 120.0 (5) | N1—Ag1—N7 | 106.44 (16) |
C16—C15—C14 | 118.8 (5) | N13—Ag1—O21 | 83.22 (14) |
C16—C15—H15A | 120.6 | N1—Ag1—O21 | 98.69 (14) |
C14—C15—H15A | 120.6 | N7—Ag1—O21 | 98.21 (14) |
C15—C16—C17 | 121.0 (6) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O21 | 0.86 | 2.28 | 2.983 (6) | 139 |
N2—H2B···O22i | 0.86 | 2.12 | 2.958 (6) | 164 |
N8—H8A···O21 | 0.86 | 2.1 | 2.959 (6) | 173 |
N8—H8B···O23ii | 0.86 | 2.07 | 2.904 (6) | 164 |
N8—H8B···N21ii | 0.86 | 2.75 | 3.545 (6) | 155 |
N14—H14A···N7 | 0.86 | 2.23 | 3.089 (6) | 174 |
N14—H14B···O23iii | 0.86 | 2.12 | 2.934 (6) | 158 |
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x, −y+1, −z+2; (iii) −x, −y, −z+2. |