Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807051549/ci2475sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807051549/ci2475Isup2.hkl |
CCDC reference: 667215
An aqueous solution (12 ml) of 3-amino-4-methylbenzenesulfonic acid (0.5 mmol) was added to solid Ag2CO3 (0.25 mmol) and stirred for several minutes until no further CO2 was given off. Triphenylphosphine (0.5 mmol) in acetonitrile (5 ml) was then added and a solution formed. Crystals of the title compound were obtained by slow evaporation of the solvent for several days at room temperature.
The amino H atoms were located in a difference map, and were refined with distance restraints of N—H = 0.90 (1) Å and H···H = 1.37 (2) Å, and with Uiso(H) = 1.5Ueq(N). H-atoms of the water molecules were located in a difference map, and were refined with distance restraints of O–H = 0.85 (1) Å and H···H = 1.39 (2) Å, and with Uiso(H) = 1.5Ueq(N). C-bound H atoms were positioned geometrically (C—H = 0.93 Å) and refined as riding, with U(H) = 1.2–1.5Ueq(C). Atom O2W is disordered across an inversion centre and it was refined with an occupancy of 0.50. The Uij components of O2W were approximated to isotropic behaviour.
Recently, intense interest has been focused on silver(I) sulfonates because of their interesting structures and properties (Han & Li, 2007a). So far, some silver(I) sulfonate compounds modified by secondary ligands that display different structures have been reported (Han & Li, 2007b). We selected 3-amino-4-methylbenzenesulfonic acid (HL) as a sulfonate ligand and triphenylphosphine (TPP) as a secondary ligand, generating a new coordination complex, [Ag(L)(TPP)(CNCH3)(H2O)].0.5H2O, which is reported here.
In compound (I), each AgI cation is four-coordinated by two N atoms one each from a 3-amino-4-methylbenzenesulfonate anion and a acetonitrile molecule, one P atom from a triphenylphosphine ligand, and one O atom from the water molecule, forming a distorted tetrahedral configuration (Fig. 1). The Ag—N (sulfonate) distance of the title complex is comparable to that found in a related structure (Han & Li, 2007b). The molecules are linked through Ow—H···O and N—H···O hydrogen bonds (Table 2) to form a ribbon like structure along the a axis.
For studies on silver sulfonates, see: Han & Li (2007a,b).
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: PROCESS-AUTO (Rigaku, 1998); 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 (Sheldrick, 1997).
Fig. 1. The structure of the title compound, showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. |
[Ag(C7H8NO3S)(C2H3N)(C18H15P)(H2O)]·0.5H2O | Z = 2 |
Mr = 624.42 | F(000) = 638 |
Triclinic, P1 | Dx = 1.448 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71069 Å |
a = 9.058 (5) Å | Cell parameters from 6198 reflections |
b = 12.300 (5) Å | θ = 3.0–27.5° |
c = 13.500 (5) Å | µ = 0.87 mm−1 |
α = 90.526 (5)° | T = 293 K |
β = 105.382 (5)° | Block, colourless |
γ = 98.637 (5)° | 0.27 × 0.24 × 0.19 mm |
V = 1431.9 (11) Å3 |
Rigaku R-AXIS RAPID diffractometer | 6265 independent reflections |
Radiation source: rotating anode | 4674 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
Detector resolution: 10.0 pixels mm-1 | θmax = 27.5°, θmin = 1.6° |
ω scans | h = 0→11 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −15→15 |
Tmin = 0.786, Tmax = 0.849 | l = −17→16 |
16198 measured reflections |
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)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.110 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0706P)2] where P = (Fo2 + 2Fc2)/3 |
6265 reflections | (Δ/σ)max = 0.001 |
351 parameters | Δρmax = 0.65 e Å−3 |
15 restraints | Δρmin = −0.60 e Å−3 |
[Ag(C7H8NO3S)(C2H3N)(C18H15P)(H2O)]·0.5H2O | γ = 98.637 (5)° |
Mr = 624.42 | V = 1431.9 (11) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.058 (5) Å | Mo Kα radiation |
b = 12.300 (5) Å | µ = 0.87 mm−1 |
c = 13.500 (5) Å | T = 293 K |
α = 90.526 (5)° | 0.27 × 0.24 × 0.19 mm |
β = 105.382 (5)° |
Rigaku R-AXIS RAPID diffractometer | 6265 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 4674 reflections with I > 2σ(I) |
Tmin = 0.786, Tmax = 0.849 | Rint = 0.032 |
16198 measured reflections |
R[F2 > 2σ(F2)] = 0.035 | 15 restraints |
wR(F2) = 0.110 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | Δρmax = 0.65 e Å−3 |
6265 reflections | Δρmin = −0.60 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 | Occ. (<1) | |
Ag1 | 0.82067 (3) | 0.71412 (2) | 0.812387 (19) | 0.05643 (11) | |
S1 | 0.24990 (7) | 0.64963 (6) | 1.03695 (5) | 0.03917 (16) | |
P1 | 0.89270 (8) | 0.83242 (6) | 0.68962 (5) | 0.03976 (17) | |
O1 | 0.1360 (2) | 0.72108 (19) | 1.00246 (19) | 0.0587 (6) | |
O2 | 0.2681 (3) | 0.6244 (2) | 1.14346 (18) | 0.0603 (6) | |
O3 | 0.2255 (2) | 0.55291 (18) | 0.96984 (19) | 0.0582 (6) | |
O1W | 0.9384 (3) | 0.5422 (2) | 0.8028 (2) | 0.0617 (6) | |
H1W1 | 0.868 (3) | 0.497 (3) | 0.819 (3) | 0.092* | |
H1W2 | 1.021 (3) | 0.550 (4) | 0.853 (2) | 0.092* | |
O2W | −0.0549 (18) | 0.4784 (15) | 0.5433 (11) | 0.237 (7) | 0.50 |
H2W1 | 0.0000 | 0.5000 | 0.5000 | 0.355* | |
H2W2 | 0.000 (12) | 0.50 (2) | 0.6040 (16) | 0.355* | 0.50 |
N1 | 0.7966 (2) | 0.6867 (2) | 0.97637 (19) | 0.0424 (5) | |
H1N1 | 0.782 (3) | 0.6141 (9) | 0.979 (3) | 0.064* | |
H1N2 | 0.8959 (17) | 0.709 (2) | 1.011 (2) | 0.064* | |
C1 | 1.0808 (3) | 0.8162 (2) | 0.6725 (2) | 0.0414 (6) | |
C2 | 1.1987 (4) | 0.8086 (3) | 0.7591 (2) | 0.0547 (8) | |
H2 | 1.1784 | 0.8062 | 0.8231 | 0.066* | |
C3 | 1.3482 (4) | 0.8046 (4) | 0.7521 (3) | 0.0700 (10) | |
H3 | 1.4282 | 0.8008 | 0.8110 | 0.084* | |
C4 | 1.3763 (4) | 0.8063 (3) | 0.6554 (3) | 0.0740 (11) | |
H4 | 1.4757 | 0.8038 | 0.6496 | 0.089* | |
C5 | 1.2592 (4) | 0.8117 (3) | 0.5700 (3) | 0.0697 (10) | |
H5 | 1.2786 | 0.8117 | 0.5057 | 0.084* | |
C6 | 1.1114 (4) | 0.8171 (3) | 0.5775 (2) | 0.0577 (8) | |
H6 | 1.0321 | 0.8214 | 0.5183 | 0.069* | |
C7 | 0.7559 (3) | 0.8004 (2) | 0.5636 (2) | 0.0455 (6) | |
C8 | 0.6856 (5) | 0.6923 (3) | 0.5389 (3) | 0.0700 (10) | |
H8 | 0.7095 | 0.6390 | 0.5865 | 0.084* | |
C9 | 0.5807 (6) | 0.6623 (4) | 0.4452 (3) | 0.0878 (13) | |
H9 | 0.5352 | 0.5891 | 0.4293 | 0.105* | |
C10 | 0.5433 (5) | 0.7408 (4) | 0.3747 (3) | 0.0885 (14) | |
H10 | 0.4722 | 0.7206 | 0.3114 | 0.106* | |
C11 | 0.6097 (5) | 0.8475 (4) | 0.3974 (3) | 0.0802 (12) | |
H11 | 0.5847 | 0.9005 | 0.3497 | 0.096* | |
C12 | 0.7160 (4) | 0.8775 (3) | 0.4929 (3) | 0.0619 (9) | |
H12 | 0.7604 | 0.9509 | 0.5087 | 0.074* | |
C13 | 0.9072 (3) | 0.9809 (2) | 0.7080 (2) | 0.0430 (6) | |
C14 | 0.7906 (4) | 1.0222 (3) | 0.7386 (2) | 0.0559 (8) | |
H14 | 0.7072 | 0.9745 | 0.7497 | 0.067* | |
C15 | 0.7994 (5) | 1.1354 (3) | 0.7526 (3) | 0.0688 (10) | |
H15 | 0.7205 | 1.1631 | 0.7719 | 0.083* | |
C16 | 0.9230 (5) | 1.2066 (3) | 0.7384 (3) | 0.0706 (10) | |
H16 | 0.9284 | 1.2821 | 0.7489 | 0.085* | |
C17 | 1.0364 (5) | 1.1670 (3) | 0.7093 (3) | 0.0662 (9) | |
H17 | 1.1197 | 1.2157 | 0.6994 | 0.079* | |
C18 | 1.0311 (4) | 1.0546 (3) | 0.6936 (2) | 0.0542 (8) | |
H18 | 1.1105 | 1.0286 | 0.6734 | 0.065* | |
C19 | 0.5426 (3) | 0.6758 (2) | 1.0080 (2) | 0.0354 (5) | |
H19 | 0.5231 | 0.6006 | 0.9914 | 0.043* | |
C20 | 0.4308 (3) | 0.7267 (2) | 1.0332 (2) | 0.0367 (6) | |
C21 | 0.4580 (3) | 0.8378 (2) | 1.0601 (2) | 0.0469 (7) | |
H21 | 0.3828 | 0.8716 | 1.0780 | 0.056* | |
C22 | 0.6002 (4) | 0.8980 (2) | 1.0597 (3) | 0.0509 (7) | |
H22 | 0.6201 | 0.9727 | 1.0787 | 0.061* | |
C23 | 0.7131 (3) | 0.8505 (2) | 1.0321 (2) | 0.0406 (6) | |
C24 | 0.8614 (3) | 0.9190 (3) | 1.0249 (3) | 0.0539 (8) | |
H24A | 0.9473 | 0.8967 | 1.0747 | 0.081* | |
H24B | 0.8581 | 0.9953 | 1.0384 | 0.081* | |
H24C | 0.8738 | 0.9089 | 0.9572 | 0.081* | |
C25 | 0.6851 (3) | 0.7374 (2) | 1.00730 (19) | 0.0346 (5) | |
N2 | 0.5710 (4) | 0.5851 (3) | 0.7540 (3) | 0.0848 (10) | |
C26 | 0.4561 (6) | 0.5415 (4) | 0.7544 (4) | 0.0868 (12) | |
C27 | 0.3062 (7) | 0.4811 (5) | 0.7599 (5) | 0.129 (2) | |
H27A | 0.3103 | 0.4036 | 0.7603 | 0.194* | |
H27B | 0.2263 | 0.4959 | 0.7012 | 0.194* | |
H27C | 0.2838 | 0.5044 | 0.8217 | 0.194* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ag1 | 0.06167 (17) | 0.06053 (17) | 0.05768 (17) | 0.01306 (12) | 0.03202 (12) | 0.01829 (11) |
S1 | 0.0240 (3) | 0.0411 (4) | 0.0537 (4) | −0.0004 (3) | 0.0156 (3) | 0.0031 (3) |
P1 | 0.0409 (4) | 0.0445 (4) | 0.0372 (4) | 0.0092 (3) | 0.0149 (3) | 0.0054 (3) |
O1 | 0.0282 (10) | 0.0637 (14) | 0.0861 (16) | 0.0109 (10) | 0.0164 (10) | 0.0087 (11) |
O2 | 0.0504 (12) | 0.0696 (14) | 0.0584 (13) | −0.0098 (11) | 0.0211 (10) | 0.0121 (11) |
O3 | 0.0404 (11) | 0.0536 (13) | 0.0801 (16) | −0.0093 (10) | 0.0252 (11) | −0.0142 (11) |
O1W | 0.0545 (13) | 0.0586 (14) | 0.0737 (16) | 0.0033 (12) | 0.0234 (12) | 0.0091 (12) |
O2W | 0.238 (10) | 0.224 (9) | 0.246 (10) | 0.058 (8) | 0.051 (8) | −0.025 (8) |
N1 | 0.0279 (10) | 0.0525 (14) | 0.0506 (14) | 0.0078 (10) | 0.0160 (10) | 0.0148 (11) |
C1 | 0.0425 (14) | 0.0416 (14) | 0.0440 (15) | 0.0119 (12) | 0.0157 (12) | 0.0043 (11) |
C2 | 0.0546 (18) | 0.068 (2) | 0.0478 (17) | 0.0212 (16) | 0.0174 (14) | 0.0113 (14) |
C3 | 0.0513 (19) | 0.094 (3) | 0.067 (2) | 0.0285 (19) | 0.0103 (17) | 0.012 (2) |
C4 | 0.053 (2) | 0.083 (3) | 0.099 (3) | 0.0261 (19) | 0.036 (2) | 0.009 (2) |
C5 | 0.068 (2) | 0.096 (3) | 0.063 (2) | 0.032 (2) | 0.0375 (19) | 0.0152 (19) |
C6 | 0.0546 (18) | 0.080 (2) | 0.0454 (17) | 0.0218 (17) | 0.0198 (14) | 0.0096 (15) |
C7 | 0.0393 (14) | 0.0556 (17) | 0.0414 (15) | 0.0054 (13) | 0.0117 (12) | −0.0015 (13) |
C8 | 0.083 (3) | 0.058 (2) | 0.062 (2) | 0.0081 (19) | 0.0110 (19) | −0.0077 (17) |
C9 | 0.093 (3) | 0.072 (3) | 0.081 (3) | −0.003 (2) | 0.002 (2) | −0.026 (2) |
C10 | 0.072 (3) | 0.115 (4) | 0.064 (3) | 0.021 (3) | −0.009 (2) | −0.023 (3) |
C11 | 0.070 (3) | 0.098 (3) | 0.061 (2) | 0.020 (2) | −0.0063 (19) | 0.005 (2) |
C12 | 0.0559 (19) | 0.067 (2) | 0.0537 (19) | 0.0054 (17) | 0.0019 (15) | 0.0075 (16) |
C13 | 0.0464 (15) | 0.0482 (15) | 0.0367 (14) | 0.0138 (13) | 0.0117 (12) | 0.0029 (11) |
C14 | 0.0483 (17) | 0.067 (2) | 0.0537 (18) | 0.0158 (16) | 0.0123 (14) | −0.0024 (15) |
C15 | 0.077 (3) | 0.074 (2) | 0.061 (2) | 0.039 (2) | 0.0134 (18) | −0.0072 (18) |
C16 | 0.104 (3) | 0.0498 (19) | 0.060 (2) | 0.029 (2) | 0.016 (2) | 0.0022 (16) |
C17 | 0.090 (3) | 0.0454 (18) | 0.065 (2) | 0.0023 (18) | 0.0281 (19) | 0.0037 (15) |
C18 | 0.066 (2) | 0.0505 (17) | 0.0548 (18) | 0.0129 (16) | 0.0290 (16) | 0.0056 (14) |
C19 | 0.0276 (12) | 0.0347 (13) | 0.0458 (14) | 0.0038 (10) | 0.0133 (10) | 0.0070 (11) |
C20 | 0.0246 (11) | 0.0392 (14) | 0.0466 (15) | 0.0015 (11) | 0.0120 (10) | 0.0068 (11) |
C21 | 0.0391 (14) | 0.0376 (14) | 0.070 (2) | 0.0051 (12) | 0.0261 (14) | 0.0026 (13) |
C22 | 0.0526 (17) | 0.0343 (14) | 0.067 (2) | −0.0023 (13) | 0.0239 (15) | −0.0010 (13) |
C23 | 0.0310 (12) | 0.0440 (15) | 0.0438 (14) | −0.0059 (12) | 0.0114 (11) | 0.0053 (11) |
C24 | 0.0406 (15) | 0.0572 (18) | 0.0580 (18) | −0.0154 (14) | 0.0160 (13) | 0.0039 (14) |
C25 | 0.0246 (11) | 0.0429 (14) | 0.0366 (13) | 0.0038 (11) | 0.0093 (10) | 0.0099 (10) |
N2 | 0.0546 (19) | 0.095 (3) | 0.094 (3) | −0.0099 (19) | 0.0144 (18) | −0.002 (2) |
C26 | 0.081 (3) | 0.092 (3) | 0.083 (3) | 0.006 (3) | 0.020 (2) | −0.009 (2) |
C27 | 0.104 (4) | 0.161 (6) | 0.116 (4) | −0.044 (4) | 0.055 (4) | −0.026 (4) |
Ag1—N1 | 2.304 (2) | C9—H9 | 0.93 |
Ag1—P1 | 2.3712 (9) | C10—C11 | 1.355 (6) |
Ag1—N2 | 2.491 (4) | C10—H10 | 0.93 |
Ag1—O1W | 2.524 (3) | C11—C12 | 1.396 (5) |
S1—O1 | 1.441 (2) | C11—H11 | 0.93 |
S1—O3 | 1.442 (2) | C12—H12 | 0.93 |
S1—O2 | 1.445 (2) | C13—C18 | 1.390 (4) |
S1—C20 | 1.779 (3) | C13—C14 | 1.391 (4) |
P1—C1 | 1.818 (3) | C14—C15 | 1.391 (5) |
P1—C7 | 1.818 (3) | C14—H14 | 0.93 |
P1—C13 | 1.821 (3) | C15—C16 | 1.371 (6) |
O1W—H1W1 | 0.854 (10) | C15—H15 | 0.93 |
O1W—H1W2 | 0.853 (10) | C16—C17 | 1.345 (6) |
O2W—O2Wi | 1.762 (17) | C16—H16 | 0.93 |
O2W—H2W1 | 0.881 (9) | C17—C18 | 1.388 (5) |
O2W—H2W2 | 0.845 (10) | C17—H17 | 0.93 |
N1—C25 | 1.411 (4) | C18—H18 | 0.93 |
N1—H1N1 | 0.885 (10) | C19—C20 | 1.379 (4) |
N1—H1N2 | 0.896 (10) | C19—C25 | 1.397 (3) |
C1—C2 | 1.373 (4) | C19—H19 | 0.93 |
C1—C6 | 1.383 (4) | C20—C21 | 1.379 (4) |
C2—C3 | 1.390 (5) | C21—C22 | 1.387 (4) |
C2—H2 | 0.93 | C21—H21 | 0.93 |
C3—C4 | 1.393 (6) | C22—C23 | 1.379 (4) |
C3—H3 | 0.9300 | C22—H22 | 0.93 |
C4—C5 | 1.353 (6) | C23—C25 | 1.397 (4) |
C4—H4 | 0.93 | C23—C24 | 1.502 (4) |
C5—C6 | 1.380 (5) | C24—H24A | 0.96 |
C5—H5 | 0.93 | C24—H24B | 0.96 |
C6—H6 | 0.93 | C24—H24C | 0.96 |
C7—C12 | 1.371 (5) | N2—C26 | 1.099 (6) |
C7—C8 | 1.382 (5) | C26—C27 | 1.467 (7) |
C8—C9 | 1.374 (5) | C27—H27A | 0.96 |
C8—H8 | 0.93 | C27—H27B | 0.96 |
C9—C10 | 1.377 (7) | C27—H27C | 0.96 |
N1—Ag1—P1 | 150.06 (7) | C9—C10—H10 | 119.9 |
N1—Ag1—N2 | 85.71 (11) | C10—C11—C12 | 119.6 (4) |
P1—Ag1—N2 | 117.20 (9) | C10—C11—H11 | 120.2 |
N1—Ag1—O1W | 94.06 (8) | C12—C11—H11 | 120.2 |
P1—Ag1—O1W | 106.81 (6) | C7—C12—C11 | 121.0 (4) |
N2—Ag1—O1W | 83.54 (11) | C7—C12—H12 | 119.5 |
O1—S1—O3 | 113.35 (15) | C11—C12—H12 | 119.5 |
O1—S1—O2 | 112.03 (15) | C18—C13—C14 | 118.7 (3) |
O3—S1—O2 | 112.98 (15) | C18—C13—P1 | 122.6 (2) |
O1—S1—C20 | 106.06 (13) | C14—C13—P1 | 118.7 (2) |
O3—S1—C20 | 106.33 (13) | C13—C14—C15 | 119.5 (3) |
O2—S1—C20 | 105.33 (13) | C13—C14—H14 | 120.2 |
C1—P1—C7 | 105.53 (13) | C15—C14—H14 | 120.2 |
C1—P1—C13 | 103.30 (13) | C16—C15—C14 | 120.9 (4) |
C7—P1—C13 | 103.75 (14) | C16—C15—H15 | 119.6 |
C1—P1—Ag1 | 112.36 (9) | C14—C15—H15 | 119.6 |
C7—P1—Ag1 | 110.54 (10) | C17—C16—C15 | 119.8 (3) |
C13—P1—Ag1 | 120.07 (10) | C17—C16—H16 | 120.1 |
Ag1—O1W—H1W1 | 97 (3) | C15—C16—H16 | 120.1 |
Ag1—O1W—H1W2 | 105 (3) | C16—C17—C18 | 121.1 (4) |
H1W1—O1W—H1W2 | 109 (2) | C16—C17—H17 | 119.5 |
H2W1—O2W—H2W2 | 109 (3) | C18—C17—H17 | 119.5 |
C25—N1—Ag1 | 117.66 (16) | C17—C18—C13 | 120.1 (3) |
C25—N1—H1N1 | 114 (2) | C17—C18—H18 | 120.0 |
Ag1—N1—H1N1 | 103 (2) | C13—C18—H18 | 120.0 |
C25—N1—H1N2 | 116 (2) | C20—C19—C25 | 120.0 (2) |
Ag1—N1—H1N2 | 98 (2) | C20—C19—H19 | 120.0 |
H1N1—N1—H1N2 | 105 (2) | C25—C19—H19 | 120.0 |
C2—C1—C6 | 119.2 (3) | C19—C20—C21 | 121.1 (2) |
C2—C1—P1 | 117.8 (2) | C19—C20—S1 | 120.8 (2) |
C6—C1—P1 | 123.0 (2) | C21—C20—S1 | 118.0 (2) |
C1—C2—C3 | 120.7 (3) | C20—C21—C22 | 118.3 (3) |
C1—C2—H2 | 119.6 | C20—C21—H21 | 120.8 |
C3—C2—H2 | 119.6 | C22—C21—H21 | 120.8 |
C2—C3—C4 | 119.0 (3) | C23—C22—C21 | 122.1 (3) |
C2—C3—H3 | 120.5 | C23—C22—H22 | 118.9 |
C4—C3—H3 | 120.5 | C21—C22—H22 | 118.9 |
C5—C4—C3 | 120.2 (3) | C22—C23—C25 | 118.8 (2) |
C5—C4—H4 | 119.9 | C22—C23—C24 | 121.0 (3) |
C3—C4—H4 | 119.9 | C25—C23—C24 | 120.1 (3) |
C4—C5—C6 | 120.6 (3) | C23—C24—H24A | 109.5 |
C4—C5—H5 | 119.7 | C23—C24—H24B | 109.5 |
C6—C5—H5 | 119.7 | H24A—C24—H24B | 109.5 |
C5—C6—C1 | 120.3 (3) | C23—C24—H24C | 109.5 |
C5—C6—H6 | 119.9 | H24A—C24—H24C | 109.5 |
C1—C6—H6 | 119.9 | H24B—C24—H24C | 109.5 |
C12—C7—C8 | 118.2 (3) | C19—C25—C23 | 119.5 (2) |
C12—C7—P1 | 123.8 (2) | C19—C25—N1 | 120.1 (2) |
C8—C7—P1 | 117.9 (3) | C23—C25—N1 | 120.2 (2) |
C9—C8—C7 | 121.0 (4) | C26—N2—Ag1 | 158.9 (4) |
C9—C8—H8 | 119.5 | N2—C26—C27 | 177.2 (6) |
C7—C8—H8 | 119.5 | C26—C27—H27A | 109.5 |
C8—C9—C10 | 119.9 (4) | C26—C27—H27B | 109.5 |
C8—C9—H9 | 120.1 | H27A—C27—H27B | 109.5 |
C10—C9—H9 | 120.1 | C26—C27—H27C | 109.5 |
C11—C10—C9 | 120.3 (4) | H27A—C27—H27C | 109.5 |
C11—C10—H10 | 119.9 | H27B—C27—H27C | 109.5 |
Symmetry code: (i) −x, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W1···O2ii | 0.85 (1) | 1.95 (1) | 2.797 (3) | 170 (4) |
O1W—H1W2···O3iii | 0.85 (1) | 2.09 (1) | 2.940 (4) | 174 (5) |
N1—H1N2···O1iii | 0.90 (1) | 2.19 (2) | 2.965 (3) | 144 (3) |
N1—H1N1···O3ii | 0.89 (1) | 2.17 (1) | 3.032 (4) | 164 (3) |
Symmetry codes: (ii) −x+1, −y+1, −z+2; (iii) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | [Ag(C7H8NO3S)(C2H3N)(C18H15P)(H2O)]·0.5H2O |
Mr | 624.42 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 9.058 (5), 12.300 (5), 13.500 (5) |
α, β, γ (°) | 90.526 (5), 105.382 (5), 98.637 (5) |
V (Å3) | 1431.9 (11) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.87 |
Crystal size (mm) | 0.27 × 0.24 × 0.19 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.786, 0.849 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16198, 6265, 4674 |
Rint | 0.032 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.035, 0.110, 1.00 |
No. of reflections | 6265 |
No. of parameters | 351 |
No. of restraints | 15 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.65, −0.60 |
Computer programs: PROCESS-AUTO (Rigaku, 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Sheldrick, 1990).
Ag1—N1 | 2.304 (2) | Ag1—N2 | 2.491 (4) |
Ag1—P1 | 2.3712 (9) | Ag1—O1W | 2.524 (3) |
N1—Ag1—P1 | 150.06 (7) | N1—Ag1—O1W | 94.06 (8) |
N1—Ag1—N2 | 85.71 (11) | P1—Ag1—O1W | 106.81 (6) |
P1—Ag1—N2 | 117.20 (9) | N2—Ag1—O1W | 83.54 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W1···O2i | 0.854 (10) | 1.952 (13) | 2.797 (3) | 170 (4) |
O1W—H1W2···O3ii | 0.853 (10) | 2.091 (12) | 2.940 (4) | 174 (5) |
N1—H1N2···O1ii | 0.896 (10) | 2.19 (2) | 2.965 (3) | 144 (3) |
N1—H1N1···O3i | 0.885 (10) | 2.171 (14) | 3.032 (4) | 164 (3) |
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) x+1, y, z. |
Recently, intense interest has been focused on silver(I) sulfonates because of their interesting structures and properties (Han & Li, 2007a). So far, some silver(I) sulfonate compounds modified by secondary ligands that display different structures have been reported (Han & Li, 2007b). We selected 3-amino-4-methylbenzenesulfonic acid (HL) as a sulfonate ligand and triphenylphosphine (TPP) as a secondary ligand, generating a new coordination complex, [Ag(L)(TPP)(CNCH3)(H2O)].0.5H2O, which is reported here.
In compound (I), each AgI cation is four-coordinated by two N atoms one each from a 3-amino-4-methylbenzenesulfonate anion and a acetonitrile molecule, one P atom from a triphenylphosphine ligand, and one O atom from the water molecule, forming a distorted tetrahedral configuration (Fig. 1). The Ag—N (sulfonate) distance of the title complex is comparable to that found in a related structure (Han & Li, 2007b). The molecules are linked through Ow—H···O and N—H···O hydrogen bonds (Table 2) to form a ribbon like structure along the a axis.