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
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- Disorder in solvent or counterion
- R factor = 0.035
- wR factor = 0.110
- Data-to-parameter ratio = 17.8
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.73 Ratio PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.51 Ratio
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 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 PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) 500 Ang. PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 500 Deg. PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C26 PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 50.00 Perc. PLAT415_ALERT_2_C Short Inter D-H..H-X H2W2 .. H27B .. 2.13 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact C24 .. C24 .. 3.18 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 6 PLAT731_ALERT_1_C Bond Calc 0.86(3), Rep 0.854(10) ...... 3.00 su-Ra O1W -H1W1 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.86(3), Rep 0.853(10) ...... 3.00 su-Ra O1W -H1W2 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.86(3), Rep 0.854(10) ...... 3.00 su-Ra O1W -H1# 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.86(3), Rep 0.853(10) ...... 3.00 su-Ra O1W -H2# 1.555 1.555 PLAT736_ALERT_1_C H...A Calc 1.95(3), Rep 1.952(13) ...... 2.31 su-Ra H1# -O2 1.555 2.667 PLAT736_ALERT_1_C H...A Calc 2.09(3), Rep 2.091(12) ...... 2.50 su-Ra H2# -O3 1.555 1.655
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 15
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 17 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 13 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
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. |
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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.