Acta Cryst. (2007). E63, m2361 [ doi:10.1107/S1600536807039955 ]
O)bis(3-methylisoquinoline-
N)silver(I)The title compound, [Ag(C10H8NO3S)(C10H9N)2], has a mononuclear structure in which the Ag+ cation is three-coordinated by two N atoms from two different 3-methylisoquinoline molecules and one O atom from a 6-aminonaphthalene-1-sulfonate anion in a distorted trigonal-planar AgN2O arrangement. A network of N-H
O hydrogen bonds consolidates the structure.
An aqueous solution (10 ml) of 6-amino-1-naphthalenesulfonic acid (0.1115 g, 0.5 mmol) was added to solid Ag2CO3 (0.069 g, 0.25 mmol) and stirred for several minutes until no further CO2 was given off; 3-methylisoquinoline (0.0715 g, 0.5 mmol) in methanol (5 ml) was then added and a white precipitate formed. The precipitate was dissolved by dropwise addition of an aqueous solution of NH3 (14 M). Crystals of (I) were obtained by evaporation of the solution for several days at room temperature.
The N-bound H atoms were located in a difference map and their positions were freely refined with Uiso(H) = 1.2Ueq(N). The C-bound H atoms were positioned geometrically (C—H = 0.93–0.96 Å) and refined as riding, with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).
Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.
| Fig. 1. The molecular structure of (I), with 30% probability displacement ellipsoids for non-H atoms. |
| [Ag(C10H8NO3S)(C10H9N)2] | Z = 2 |
| Mr = 616.47 | F000 = 628 |
| Triclinic, P1 | Dx = 1.562 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation λ = 0.71073 Å |
| a = 9.8810 (14) Å | Cell parameters from 5933 reflections |
| b = 10.2220 (17) Å | θ = 2.0–28.3º |
| c = 13.256 (2) Å | µ = 0.89 mm−1 |
| α = 80.108 (11)º | T = 292 (2) K |
| β = 86.653 (11)º | Block, colourless |
| γ = 84.143 (10)º | 0.35 × 0.33 × 0.29 mm |
| V = 1311.0 (4) Å3 |
| Bruker SMART APEX CCD diffractometer | 5933 independent reflections |
| Radiation source: fine-focus sealed tube | 2404 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.064 |
| T = 292(2) K | θmax = 28.3º |
| ω scans | θmin = 2.0º |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→12 |
| Tmin = 0.709, Tmax = 0.766 | k = −13→10 |
| 8844 measured reflections | l = −17→17 |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: difmap and geom |
| R[F2 > 2σ(F2)] = 0.048 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.074 | w = 1/[σ2(Fo2)] where P = (Fo2 + 2Fc2)/3 |
| S = 0.76 | (Δ/σ)max = 0.001 |
| 5933 reflections | Δρmax = 0.38 e Å−3 |
| 351 parameters | Δρmin = −0.35 e Å−3 |
| 3 restraints | Extinction correction: none |
| Primary atom site location: structure-invariant direct methods |
| [Ag(C10H8NO3S)(C10H9N)2] | γ = 84.143 (10)º |
| Mr = 616.47 | V = 1311.0 (4) Å3 |
| Triclinic, P1 | Z = 2 |
| a = 9.8810 (14) Å | Mo Kα |
| b = 10.2220 (17) Å | µ = 0.89 mm−1 |
| c = 13.256 (2) Å | T = 292 (2) K |
| α = 80.108 (11)º | 0.35 × 0.33 × 0.29 mm |
| β = 86.653 (11)º |
| Bruker SMART APEX CCD diffractometer | 5933 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2404 reflections with I > 2σ(I) |
| Tmin = 0.709, Tmax = 0.766 | Rint = 0.064 |
| 8844 measured reflections |
| R[F2 > 2σ(F2)] = 0.048 | 3 restraints |
| wR(F2) = 0.074 | H atoms treated by a mixture of independent and constrained refinement |
| S = 0.76 | Δρmax = 0.38 e Å−3 |
| 5933 reflections | Δρmin = −0.35 e Å−3 |
| 351 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 > 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 | 0.45151 (4) | 0.67693 (4) | 0.24609 (3) | 0.05828 (15) | |
| C1 | 0.3993 (5) | 0.4468 (5) | 0.4152 (4) | 0.0483 (13) | |
| H1 | 0.4766 | 0.4132 | 0.3812 | 0.058* | |
| C2 | 0.3389 (5) | 0.3592 (5) | 0.4960 (4) | 0.0488 (14) | |
| C3 | 0.3883 (6) | 0.2245 (6) | 0.5219 (5) | 0.0706 (18) | |
| H3 | 0.4644 | 0.1905 | 0.4868 | 0.085* | |
| C4 | 0.3243 (7) | 0.1436 (6) | 0.5989 (5) | 0.083 (2) | |
| H4 | 0.3559 | 0.0539 | 0.6150 | 0.099* | |
| C5 | 0.2106 (8) | 0.1950 (7) | 0.6541 (5) | 0.089 (2) | |
| H5 | 0.1692 | 0.1400 | 0.7078 | 0.107* | |
| C6 | 0.1621 (6) | 0.3237 (6) | 0.6291 (4) | 0.0735 (18) | |
| H6 | 0.0869 | 0.3558 | 0.6662 | 0.088* | |
| C7 | 0.2215 (5) | 0.4123 (6) | 0.5483 (4) | 0.0534 (14) | |
| C8 | 0.1762 (5) | 0.5456 (5) | 0.5152 (4) | 0.0599 (15) | |
| H8 | 0.1007 | 0.5837 | 0.5486 | 0.072* | |
| C9 | 0.2389 (5) | 0.6209 (5) | 0.4359 (4) | 0.0523 (14) | |
| C10 | 0.1897 (5) | 0.7653 (5) | 0.3960 (4) | 0.0753 (17) | |
| H10A | 0.1826 | 0.7775 | 0.3230 | 0.113* | |
| H10B | 0.2533 | 0.8227 | 0.4124 | 0.113* | |
| H10C | 0.1021 | 0.7870 | 0.4273 | 0.113* | |
| C13 | 0.5358 (4) | 0.9633 (4) | 0.1512 (3) | 0.0332 (11) | |
| C14 | 0.6092 (4) | 1.0543 (4) | 0.0927 (3) | 0.0397 (12) | |
| H14 | 0.5902 | 1.1441 | 0.0973 | 0.048* | |
| C15 | 0.7154 (4) | 1.0151 (4) | 0.0239 (3) | 0.0359 (12) | |
| C16 | 0.7952 (5) | 1.1056 (5) | −0.0401 (4) | 0.0494 (14) | |
| H16 | 0.7775 | 1.1966 | −0.0397 | 0.059* | |
| C17 | 0.8978 (5) | 1.0607 (5) | −0.1025 (4) | 0.0533 (14) | |
| H17 | 0.9502 | 1.1209 | −0.1439 | 0.064* | |
| C18 | 0.9241 (5) | 0.9244 (5) | −0.1040 (4) | 0.0497 (14) | |
| H18 | 0.9947 | 0.8948 | −0.1465 | 0.060* | |
| C19 | 0.8488 (5) | 0.8337 (5) | −0.0447 (3) | 0.0445 (13) | |
| H19 | 0.8675 | 0.7432 | −0.0473 | 0.053* | |
| C20 | 0.7421 (4) | 0.8779 (4) | 0.0207 (3) | 0.0351 (11) | |
| C21 | 0.6583 (4) | 0.7912 (4) | 0.0831 (4) | 0.0412 (13) | |
| H21 | 0.6740 | 0.7007 | 0.0797 | 0.049* | |
| C22 | 0.4221 (4) | 1.0036 (4) | 0.2248 (3) | 0.0547 (14) | |
| H22A | 0.4298 | 0.9450 | 0.2895 | 0.082* | |
| H22B | 0.3358 | 0.9976 | 0.1970 | 0.082* | |
| H22C | 0.4288 | 1.0936 | 0.2344 | 0.082* | |
| C23 | 0.8414 (4) | 0.3038 (4) | 0.2552 (3) | 0.0328 (11) | |
| C24 | 0.8408 (5) | 0.1891 (4) | 0.3251 (4) | 0.0443 (13) | |
| H24 | 0.7596 | 0.1508 | 0.3434 | 0.053* | |
| C25 | 0.9623 (5) | 0.1283 (4) | 0.3697 (4) | 0.0504 (14) | |
| H25 | 0.9607 | 0.0495 | 0.4166 | 0.061* | |
| C26 | 0.9638 (4) | 0.3629 (4) | 0.2255 (3) | 0.0299 (11) | |
| C27 | 0.9763 (4) | 0.4796 (4) | 0.1512 (3) | 0.0349 (12) | |
| H27 | 0.8980 | 0.5248 | 0.1217 | 0.042* | |
| C28 | 1.0982 (4) | 0.5274 (4) | 0.1217 (3) | 0.0383 (12) | |
| H28 | 1.1019 | 0.6034 | 0.0720 | 0.046* | |
| C29 | 1.2213 (4) | 0.4623 (5) | 0.1660 (4) | 0.0383 (12) | |
| C30 | 1.2132 (5) | 0.3537 (4) | 0.2412 (3) | 0.0382 (12) | |
| H30 | 1.2918 | 0.3133 | 0.2729 | 0.046* | |
| C31 | 1.0875 (4) | 0.3017 (4) | 0.2714 (3) | 0.0331 (11) | |
| C32 | 1.0812 (5) | 0.1832 (5) | 0.3453 (4) | 0.0496 (14) | |
| H32 | 1.1599 | 0.1431 | 0.3772 | 0.060* | |
| O1 | 0.7019 (3) | 0.3847 (3) | 0.0920 (2) | 0.0576 (9) | |
| O2 | 0.5813 (3) | 0.2902 (3) | 0.2478 (2) | 0.0493 (9) | |
| O3 | 0.6625 (3) | 0.5087 (3) | 0.2318 (2) | 0.0513 (9) | |
| S1 | 0.68386 (11) | 0.37694 (12) | 0.20242 (10) | 0.0403 (3) | |
| N1 | 1.3436 (4) | 0.5164 (4) | 0.1317 (3) | 0.0478 (12) | |
| N2 | 0.3539 (4) | 0.5727 (4) | 0.3847 (3) | 0.0435 (10) | |
| N3 | 0.5578 (4) | 0.8287 (3) | 0.1470 (3) | 0.0403 (10) | |
| H1N | 1.419 (4) | 0.461 (4) | 0.147 (3) | 0.060* | |
| H2N | 1.363 (5) | 0.556 (4) | 0.075 (3) | 0.060* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Ag1 | 0.0562 (3) | 0.0463 (3) | 0.0664 (3) | −0.0042 (2) | 0.0173 (2) | 0.0005 (2) |
| C1 | 0.051 (3) | 0.056 (4) | 0.042 (3) | −0.014 (3) | −0.004 (3) | −0.012 (3) |
| C2 | 0.057 (4) | 0.050 (4) | 0.043 (4) | −0.023 (3) | −0.013 (3) | −0.004 (3) |
| C3 | 0.071 (4) | 0.061 (4) | 0.081 (5) | −0.016 (4) | −0.017 (4) | −0.006 (4) |
| C4 | 0.100 (6) | 0.061 (4) | 0.087 (6) | −0.029 (4) | −0.046 (5) | 0.012 (4) |
| C5 | 0.116 (6) | 0.083 (5) | 0.070 (5) | −0.056 (5) | −0.016 (5) | 0.015 (4) |
| C6 | 0.097 (5) | 0.088 (5) | 0.037 (4) | −0.040 (4) | 0.011 (3) | −0.001 (4) |
| C7 | 0.066 (4) | 0.069 (4) | 0.030 (3) | −0.029 (3) | 0.005 (3) | −0.009 (3) |
| C8 | 0.068 (4) | 0.070 (4) | 0.045 (4) | −0.021 (3) | 0.020 (3) | −0.019 (3) |
| C9 | 0.055 (4) | 0.058 (4) | 0.046 (4) | −0.011 (3) | 0.015 (3) | −0.017 (3) |
| C10 | 0.076 (4) | 0.064 (4) | 0.077 (4) | 0.004 (3) | 0.029 (3) | −0.003 (4) |
| C13 | 0.033 (3) | 0.030 (3) | 0.036 (3) | −0.002 (2) | −0.005 (2) | −0.004 (2) |
| C14 | 0.046 (3) | 0.028 (3) | 0.048 (3) | −0.001 (2) | −0.006 (3) | −0.012 (3) |
| C15 | 0.035 (3) | 0.034 (3) | 0.039 (3) | −0.005 (2) | −0.009 (2) | −0.005 (2) |
| C16 | 0.055 (4) | 0.040 (3) | 0.056 (4) | −0.015 (3) | 0.000 (3) | −0.010 (3) |
| C17 | 0.050 (3) | 0.062 (4) | 0.050 (4) | −0.022 (3) | 0.000 (3) | −0.006 (3) |
| C18 | 0.046 (3) | 0.060 (4) | 0.048 (4) | −0.007 (3) | 0.000 (3) | −0.024 (3) |
| C19 | 0.046 (3) | 0.045 (3) | 0.043 (3) | 0.002 (3) | −0.001 (3) | −0.015 (3) |
| C20 | 0.035 (3) | 0.032 (3) | 0.041 (3) | −0.004 (2) | −0.006 (2) | −0.011 (3) |
| C21 | 0.043 (3) | 0.032 (3) | 0.051 (4) | −0.001 (2) | −0.005 (3) | −0.013 (3) |
| C22 | 0.048 (3) | 0.054 (3) | 0.063 (4) | −0.002 (3) | 0.007 (3) | −0.017 (3) |
| C23 | 0.032 (3) | 0.033 (3) | 0.034 (3) | −0.003 (2) | 0.001 (2) | −0.008 (2) |
| C24 | 0.050 (3) | 0.036 (3) | 0.048 (3) | −0.013 (3) | 0.002 (3) | −0.005 (3) |
| C25 | 0.068 (4) | 0.035 (3) | 0.042 (3) | −0.003 (3) | −0.004 (3) | 0.009 (3) |
| C26 | 0.034 (3) | 0.026 (2) | 0.029 (3) | 0.001 (2) | −0.002 (2) | −0.006 (2) |
| C27 | 0.030 (3) | 0.028 (3) | 0.045 (3) | 0.000 (2) | −0.006 (2) | −0.002 (2) |
| C28 | 0.040 (3) | 0.031 (3) | 0.043 (3) | −0.006 (2) | −0.007 (3) | 0.000 (2) |
| C29 | 0.027 (3) | 0.046 (3) | 0.048 (3) | −0.005 (2) | −0.003 (3) | −0.021 (3) |
| C30 | 0.037 (3) | 0.035 (3) | 0.043 (3) | 0.005 (2) | −0.012 (3) | −0.009 (3) |
| C31 | 0.037 (3) | 0.035 (3) | 0.028 (3) | 0.000 (2) | −0.006 (2) | −0.007 (2) |
| C32 | 0.055 (4) | 0.048 (3) | 0.040 (3) | 0.000 (3) | −0.004 (3) | 0.010 (3) |
| O1 | 0.048 (2) | 0.085 (3) | 0.038 (2) | −0.0121 (19) | −0.0052 (18) | −0.002 (2) |
| O2 | 0.0342 (19) | 0.048 (2) | 0.068 (2) | −0.0149 (16) | 0.0086 (18) | −0.0135 (18) |
| O3 | 0.0411 (19) | 0.0293 (18) | 0.084 (3) | 0.0022 (15) | −0.0004 (18) | −0.0138 (18) |
| S1 | 0.0297 (7) | 0.0384 (8) | 0.0523 (9) | −0.0043 (6) | 0.0004 (6) | −0.0065 (7) |
| N1 | 0.028 (2) | 0.064 (3) | 0.052 (3) | −0.010 (2) | 0.000 (2) | −0.008 (3) |
| N2 | 0.051 (3) | 0.044 (3) | 0.037 (3) | −0.009 (2) | 0.000 (2) | −0.011 (2) |
| N3 | 0.043 (2) | 0.031 (2) | 0.047 (3) | −0.0069 (19) | −0.006 (2) | −0.003 (2) |
| Ag1—N3 | 2.170 (4) | C18—C19 | 1.361 (6) |
| Ag1—N2 | 2.184 (4) | C18—H18 | 0.9300 |
| Ag1—O3 | 2.583 (3) | C19—C20 | 1.414 (5) |
| C1—N2 | 1.321 (5) | C19—H19 | 0.9300 |
| C1—C2 | 1.417 (6) | C20—C21 | 1.404 (6) |
| C1—H1 | 0.9300 | C21—N3 | 1.337 (5) |
| C2—C3 | 1.404 (6) | C21—H21 | 0.9300 |
| C2—C7 | 1.425 (6) | C22—H22A | 0.9600 |
| C3—C4 | 1.366 (7) | C22—H22B | 0.9600 |
| C3—H3 | 0.9300 | C22—H22C | 0.9600 |
| C4—C5 | 1.411 (8) | C23—C24 | 1.364 (5) |
| C4—H4 | 0.9300 | C23—C26 | 1.412 (5) |
| C5—C6 | 1.345 (7) | C23—S1 | 1.783 (4) |
| C5—H5 | 0.9300 | C24—C25 | 1.407 (6) |
| C6—C7 | 1.419 (6) | C24—H24 | 0.9300 |
| C6—H6 | 0.9300 | C25—C32 | 1.351 (6) |
| C7—C8 | 1.393 (6) | C25—H25 | 0.9300 |
| C8—C9 | 1.351 (6) | C26—C27 | 1.421 (5) |
| C8—H8 | 0.9300 | C26—C31 | 1.434 (5) |
| C9—N2 | 1.380 (5) | C27—C28 | 1.358 (5) |
| C9—C10 | 1.520 (6) | C27—H27 | 0.9300 |
| C10—H10A | 0.9600 | C28—C29 | 1.432 (5) |
| C10—H10B | 0.9600 | C28—H28 | 0.9300 |
| C10—H10C | 0.9600 | C29—C30 | 1.364 (6) |
| C13—C14 | 1.349 (5) | C29—N1 | 1.400 (5) |
| C13—N3 | 1.381 (5) | C30—C31 | 1.411 (5) |
| C13—C22 | 1.516 (5) | C30—H30 | 0.9300 |
| C14—C15 | 1.422 (5) | C31—C32 | 1.425 (6) |
| C14—H14 | 0.9300 | C32—H32 | 0.9300 |
| C15—C20 | 1.408 (5) | O1—S1 | 1.453 (3) |
| C15—C16 | 1.414 (6) | O2—S1 | 1.450 (3) |
| C16—C17 | 1.364 (6) | O3—S1 | 1.457 (3) |
| C16—H16 | 0.9300 | N1—H1N | 0.90 (3) |
| C17—C18 | 1.394 (6) | N1—H2N | 0.81 (3) |
| C17—H17 | 0.9300 | ||
| N3—Ag1—N2 | 159.18 (13) | C21—C20—C19 | 123.2 (4) |
| N3—Ag1—O3 | 89.17 (12) | C15—C20—C19 | 119.5 (5) |
| N2—Ag1—O3 | 98.76 (13) | N3—C21—C20 | 125.0 (4) |
| N2—C1—C2 | 124.9 (5) | N3—C21—H21 | 117.5 |
| N2—C1—H1 | 117.5 | C20—C21—H21 | 117.5 |
| C2—C1—H1 | 117.5 | C13—C22—H22A | 109.5 |
| C3—C2—C1 | 122.3 (6) | C13—C22—H22B | 109.5 |
| C3—C2—C7 | 120.7 (5) | H22A—C22—H22B | 109.5 |
| C1—C2—C7 | 117.0 (5) | C13—C22—H22C | 109.5 |
| C4—C3—C2 | 119.9 (6) | H22A—C22—H22C | 109.5 |
| C4—C3—H3 | 120.1 | H22B—C22—H22C | 109.5 |
| C2—C3—H3 | 120.1 | C24—C23—C26 | 120.7 (4) |
| C3—C4—C5 | 120.5 (6) | C24—C23—S1 | 118.3 (4) |
| C3—C4—H4 | 119.8 | C26—C23—S1 | 121.0 (3) |
| C5—C4—H4 | 119.8 | C23—C24—C25 | 120.5 (4) |
| C6—C5—C4 | 120.0 (7) | C23—C24—H24 | 119.8 |
| C6—C5—H5 | 120.0 | C25—C24—H24 | 119.8 |
| C4—C5—H5 | 120.0 | C32—C25—C24 | 120.8 (5) |
| C5—C6—C7 | 122.5 (6) | C32—C25—H25 | 119.6 |
| C5—C6—H6 | 118.8 | C24—C25—H25 | 119.6 |
| C7—C6—H6 | 118.8 | C23—C26—C27 | 125.2 (4) |
| C8—C7—C6 | 126.5 (6) | C23—C26—C31 | 118.9 (4) |
| C8—C7—C2 | 117.0 (5) | C27—C26—C31 | 115.9 (4) |
| C6—C7—C2 | 116.5 (5) | C28—C27—C26 | 122.4 (4) |
| C9—C8—C7 | 121.8 (5) | C28—C27—H27 | 118.8 |
| C9—C8—H8 | 119.1 | C26—C27—H27 | 118.8 |
| C7—C8—H8 | 119.1 | C27—C28—C29 | 120.8 (4) |
| C8—C9—N2 | 122.5 (5) | C27—C28—H28 | 119.6 |
| C8—C9—C10 | 123.1 (5) | C29—C28—H28 | 119.6 |
| N2—C9—C10 | 114.4 (5) | C30—C29—N1 | 123.4 (4) |
| C9—C10—H10A | 109.5 | C30—C29—C28 | 118.7 (4) |
| C9—C10—H10B | 109.5 | N1—C29—C28 | 117.9 (5) |
| H10A—C10—H10B | 109.5 | C29—C30—C31 | 121.0 (4) |
| C9—C10—H10C | 109.5 | C29—C30—H30 | 119.5 |
| H10A—C10—H10C | 109.5 | C31—C30—H30 | 119.5 |
| H10B—C10—H10C | 109.5 | C30—C31—C32 | 120.7 (4) |
| C14—C13—N3 | 122.4 (4) | C30—C31—C26 | 121.0 (4) |
| C14—C13—C22 | 121.6 (4) | C32—C31—C26 | 118.2 (4) |
| N3—C13—C22 | 116.0 (4) | C25—C32—C31 | 120.8 (4) |
| C13—C14—C15 | 121.0 (4) | C25—C32—H32 | 119.6 |
| C13—C14—H14 | 119.5 | C31—C32—H32 | 119.6 |
| C15—C14—H14 | 119.5 | S1—O3—Ag1 | 134.03 (16) |
| C20—C15—C16 | 118.8 (4) | O2—S1—O1 | 113.23 (19) |
| C20—C15—C14 | 117.5 (4) | O2—S1—O3 | 112.74 (17) |
| C16—C15—C14 | 123.7 (4) | O1—S1—O3 | 111.9 (2) |
| C17—C16—C15 | 120.6 (5) | O2—S1—C23 | 106.3 (2) |
| C17—C16—H16 | 119.7 | O1—S1—C23 | 106.46 (19) |
| C15—C16—H16 | 119.7 | O3—S1—C23 | 105.52 (18) |
| C16—C17—C18 | 120.0 (5) | C29—N1—H1N | 115 (3) |
| C16—C17—H17 | 120.0 | C29—N1—H2N | 128 (3) |
| C18—C17—H17 | 120.0 | H1N—N1—H2N | 103 (4) |
| C19—C18—C17 | 121.5 (5) | C1—N2—C9 | 116.8 (4) |
| C19—C18—H18 | 119.3 | C1—N2—Ag1 | 116.9 (3) |
| C17—C18—H18 | 119.3 | C9—N2—Ag1 | 125.9 (4) |
| C18—C19—C20 | 119.6 (4) | C21—N3—C13 | 116.8 (4) |
| C18—C19—H19 | 120.2 | C21—N3—Ag1 | 119.1 (3) |
| C20—C19—H19 | 120.2 | C13—N3—Ag1 | 123.9 (3) |
| C21—C20—C15 | 117.3 (4) | ||
| N2—C1—C2—C3 | 177.0 (4) | C27—C28—C29—C30 | −2.2 (6) |
| N2—C1—C2—C7 | −0.7 (7) | C27—C28—C29—N1 | 179.7 (4) |
| C1—C2—C3—C4 | −178.5 (5) | N1—C29—C30—C31 | −178.8 (4) |
| C7—C2—C3—C4 | −0.8 (8) | C28—C29—C30—C31 | 3.2 (6) |
| C2—C3—C4—C5 | −1.4 (9) | C29—C30—C31—C32 | 176.0 (4) |
| C3—C4—C5—C6 | 1.9 (9) | C29—C30—C31—C26 | −1.2 (6) |
| C4—C5—C6—C7 | −0.2 (9) | C23—C26—C31—C30 | 177.3 (4) |
| C5—C6—C7—C8 | 178.1 (6) | C27—C26—C31—C30 | −1.9 (6) |
| C5—C6—C7—C2 | −1.9 (8) | C23—C26—C31—C32 | 0.1 (6) |
| C3—C2—C7—C8 | −177.6 (5) | C27—C26—C31—C32 | −179.1 (4) |
| C1—C2—C7—C8 | 0.2 (7) | C24—C25—C32—C31 | −2.0 (7) |
| C3—C2—C7—C6 | 2.4 (7) | C30—C31—C32—C25 | −175.8 (4) |
| C1—C2—C7—C6 | −179.8 (4) | C26—C31—C32—C25 | 1.5 (6) |
| C6—C7—C8—C9 | −178.8 (5) | N3—Ag1—O3—S1 | −126.1 (3) |
| C2—C7—C8—C9 | 1.1 (7) | N2—Ag1—O3—S1 | 73.2 (3) |
| C7—C8—C9—N2 | −2.1 (8) | Ag1—O3—S1—O2 | −44.1 (3) |
| C7—C8—C9—C10 | 178.2 (5) | Ag1—O3—S1—O1 | 84.9 (3) |
| N3—C13—C14—C15 | −0.9 (7) | Ag1—O3—S1—C23 | −159.8 (2) |
| C22—C13—C14—C15 | −179.9 (4) | C24—C23—S1—O2 | −1.0 (4) |
| C13—C14—C15—C20 | −1.1 (6) | C26—C23—S1—O2 | 179.0 (3) |
| C13—C14—C15—C16 | 179.4 (4) | C24—C23—S1—O1 | −122.0 (4) |
| C20—C15—C16—C17 | −1.2 (6) | C26—C23—S1—O1 | 58.0 (4) |
| C14—C15—C16—C17 | 178.3 (4) | C24—C23—S1—O3 | 118.9 (4) |
| C15—C16—C17—C18 | 0.5 (7) | C26—C23—S1—O3 | −61.0 (4) |
| C16—C17—C18—C19 | 0.4 (7) | C2—C1—N2—C9 | −0.1 (7) |
| C17—C18—C19—C20 | −0.5 (7) | C2—C1—N2—Ag1 | −172.5 (3) |
| C16—C15—C20—C21 | −178.2 (4) | C8—C9—N2—C1 | 1.5 (7) |
| C14—C15—C20—C21 | 2.3 (6) | C10—C9—N2—C1 | −178.7 (4) |
| C16—C15—C20—C19 | 1.0 (6) | C8—C9—N2—Ag1 | 173.1 (4) |
| C14—C15—C20—C19 | −178.5 (4) | C10—C9—N2—Ag1 | −7.1 (6) |
| C18—C19—C20—C21 | 179.0 (4) | N3—Ag1—N2—C1 | −125.3 (4) |
| C18—C19—C20—C15 | −0.2 (6) | O3—Ag1—N2—C1 | −13.9 (3) |
| C15—C20—C21—N3 | −1.8 (7) | N3—Ag1—N2—C9 | 63.1 (6) |
| C19—C20—C21—N3 | 179.0 (4) | O3—Ag1—N2—C9 | 174.5 (3) |
| C26—C23—C24—C25 | 0.7 (7) | C20—C21—N3—C13 | 0.0 (6) |
| S1—C23—C24—C25 | −179.3 (3) | C20—C21—N3—Ag1 | −174.9 (3) |
| C23—C24—C25—C32 | 0.9 (7) | C14—C13—N3—C21 | 1.4 (6) |
| C24—C23—C26—C27 | 178.0 (4) | C22—C13—N3—C21 | −179.5 (4) |
| S1—C23—C26—C27 | −2.1 (6) | C14—C13—N3—Ag1 | 176.0 (3) |
| C24—C23—C26—C31 | −1.1 (6) | C22—C13—N3—Ag1 | −4.9 (5) |
| S1—C23—C26—C31 | 178.9 (3) | N2—Ag1—N3—C21 | 136.8 (4) |
| C23—C26—C27—C28 | −176.2 (4) | O3—Ag1—N3—C21 | 23.9 (3) |
| C31—C26—C27—C28 | 2.9 (6) | N2—Ag1—N3—C13 | −37.6 (6) |
| C26—C27—C28—C29 | −0.9 (6) | O3—Ag1—N3—C13 | −150.6 (3) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1N···O2i | 0.90 (4) | 2.51 (4) | 3.365 (5) | 160 (3) |
| N1—H2N···O1ii | 0.81 (4) | 2.30 (4) | 3.008 (5) | 146 (4) |
| Symmetry codes: (i) x+1, y, z; (ii) −x+2, −y+1, −z. |
| Ag1—N3 | 2.170 (4) | Ag1—O3 | 2.583 (3) |
| Ag1—N2 | 2.184 (4) | ||
| N3—Ag1—N2 | 159.18 (13) | N2—Ag1—O3 | 98.76 (13) |
| N3—Ag1—O3 | 89.17 (12) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1N···O2i | 0.90 (4) | 2.51 (4) | 3.365 (5) | 160 (3) |
| N1—H2N···O1ii | 0.81 (4) | 2.30 (4) | 3.008 (5) | 146 (4) |
| Symmetry codes: (i) x+1, y, z; (ii) −x+2, −y+1, −z. |
The authors thank JiLin Agriculture Science and Technology College (China) for support.
Bruker (1999). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Li, Y.-J., Shangguan, S.-P. & Dong, X.-W. (2007). Acta Cryst. E63, m1806–?.
Sheldrick, G. M. (1990). SHELXTL-Plus. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.
In this paper, the structure of the title compound, (I) (Fig. 1), containing two 3-methylisoquinoline molecules and one 6-amino-1-naphthalenesulfonate (L) anion is described.
In (I), two 3-methylisoquinoline molecules and one L anion are coordinated to the metal, resulting in a highly distorted trigonal planar coordination geometry for Ag (Table 1). Atoms Ag1, N2, N3 and O3 are close to coplanar and the bond-angle sum about Ag is 347.11°. The Ag—N distances in (I) are similar to the equivalent values in a related compound (Li et al., 2007). The dihedral angle between the quinoline rings of the two coordinated 3-methylisoquinoline molecules is 22.2 (3)°.
The structure of (I) is completed by N—H···O hydrogen bonds (Table 2) to result in chains propagating in [100].