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The title compound, [Ag(C8H10NO3S)(C18H15P)2]·CH3CN, has a mononuclear structure, where the AgI cation is three-coordinated by two triphenyl­phosphine ligands and one N atom from the 2-amino-3,5-dimethyl­benzene­sulfonate anion in a distorted trigonal-planar AgP2N arrangement. A network of N—H...O hydrogen bonds helps to consolidate the packing.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807048076/hb2567sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807048076/hb2567Isup2.hkl
Contains datablock I

CCDC reference: 667108

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.034
  • wR factor = 0.092
  • Data-to-parameter ratio = 19.0

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.62 Ratio PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.09 Ratio
Alert level C PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C21 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C24 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C19 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C22 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C45 PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C19 -C24 1.36 Ang.
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 PLAT794_ALERT_5_G Check Predicted Bond Valency for Ag1 (9) 0.94 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 3
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A PUBL022_ALERT_1_A There is a mismatched ~ on line 233 '[Ag (C10 H8 N O3 S) (C18 H15 P)2~], C2 H3 N' If you require a ~ then it should be escaped with a \, i.e. \~ Otherwise there must be a matching closing ~, e.g. C~2~H~4~
1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing

Comment top

Cote & Shimizu have reviewed recent progress in the solid-state coordination and structural chemistry of sulfonates complexes as well as their properties in the gas sorption (Cote & Shimizu, 2003). However, sulfonate are generally perceived as weaker ligands regarding their coordinating ability (Han & Li, 2007a). Herein, we present the synthesis and structure of the title compound, (I), [Ag(tpp)2(L)].CNCH3, where tpp = triphenylphosphine and HL= 2-amino-3,5-dimethylbenzenesulfonic acid.

The AgI cation is three-coordinated by two P atoms from two triphenylphosphine ligands and one N atom from the L anion in a distorted trigonal-planar AgP2N arrangement (Fig. 1, Table 1). The Ag—N (sulfonate) distance in (I) is similar to the equivalent value in a related compound (Han & Li, 2007b). Finally, the molecules are linked through N—H···O hydrogen bonds (Table 2), which help to consolidate the structure of (I).

Related literature top

For studies on related silver sulfonates, see: Han & Li, (2007a,b). For a review on the structural chemistry and properties of sulfonate complexes, see: Cote & Shimizu (2003).

Experimental top

An aqueous solution (10 ml) of 2-amino-3,-5-dimethylbenzenesulfonic 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 (7 ml) was then added and a solution was formed. Colourless blocks of (I) were obtained by evaporation of the solution for several days at room temperature.

Refinement top

H atoms bonded to N atom were located in a difference map and refined freely, with Uiso(H) = 1.2Ueq(N). H atoms bonded to C atom 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).

Structure description top

Cote & Shimizu have reviewed recent progress in the solid-state coordination and structural chemistry of sulfonates complexes as well as their properties in the gas sorption (Cote & Shimizu, 2003). However, sulfonate are generally perceived as weaker ligands regarding their coordinating ability (Han & Li, 2007a). Herein, we present the synthesis and structure of the title compound, (I), [Ag(tpp)2(L)].CNCH3, where tpp = triphenylphosphine and HL= 2-amino-3,5-dimethylbenzenesulfonic acid.

The AgI cation is three-coordinated by two P atoms from two triphenylphosphine ligands and one N atom from the L anion in a distorted trigonal-planar AgP2N arrangement (Fig. 1, Table 1). The Ag—N (sulfonate) distance in (I) is similar to the equivalent value in a related compound (Han & Li, 2007b). Finally, the molecules are linked through N—H···O hydrogen bonds (Table 2), which help to consolidate the structure of (I).

For studies on related silver sulfonates, see: Han & Li, (2007a,b). For a review on the structural chemistry and properties of sulfonate complexes, see: Cote & Shimizu (2003).

Computing details top

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).

Figures top
[Figure 1] Fig. 1. The structure of (I), with displacement ellipsoids drawn at the 30% probability level (H atoms omitted for clarity).
(2-Amino-3,5-dimethylbenzenesulfonato-κN)bis(triphenylphosphine-κP)silver(I) acetonitrile solvate top
Crystal data top
[Ag(C8H10NO3S)(C18H15P)2]·C2H3NF(000) = 1800
Mr = 873.69Dx = 1.365 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 28308 reflections
a = 13.782 (3) Åθ = 3.0–27.5°
b = 12.252 (3) ŵ = 0.64 mm1
c = 25.243 (5) ÅT = 293 K
β = 94.32 (3)°Block, colorless
V = 4250.5 (15) Å30.26 × 0.21 × 0.18 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID
diffractometer
9612 independent reflections
Radiation source: rotating anode7595 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.047
Detector resolution: 10.0 pixels mm-1θmax = 27.5°, θmin = 3.2°
ω scansh = 1717
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
k = 1515
Tmin = 0.841, Tmax = 0.892l = 3232
39847 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: difmap and geom
wR(F2) = 0.092H atoms treated by a mixture of independent and constrained refinement
S = 0.84 w = 1/[σ2(Fo2) + (0.0487P)2 + 4.2132P]
where P = (Fo2 + 2Fc2)/3
9612 reflections(Δ/σ)max = 0.003
506 parametersΔρmax = 0.45 e Å3
3 restraintsΔρmin = 0.45 e Å3
Crystal data top
[Ag(C8H10NO3S)(C18H15P)2]·C2H3NV = 4250.5 (15) Å3
Mr = 873.69Z = 4
Monoclinic, P21/nMo Kα radiation
a = 13.782 (3) ŵ = 0.64 mm1
b = 12.252 (3) ÅT = 293 K
c = 25.243 (5) Å0.26 × 0.21 × 0.18 mm
β = 94.32 (3)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer
9612 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
7595 reflections with I > 2σ(I)
Tmin = 0.841, Tmax = 0.892Rint = 0.047
39847 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0343 restraints
wR(F2) = 0.092H atoms treated by a mixture of independent and constrained refinement
S = 0.84Δρmax = 0.45 e Å3
9612 reflectionsΔρmin = 0.45 e Å3
506 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.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ag10.817193 (13)1.130397 (16)0.175155 (7)0.03824 (7)
C10.68522 (18)0.9235 (2)0.09214 (9)0.0382 (5)
C20.76198 (19)0.8582 (2)0.11134 (10)0.0450 (6)
H20.81410.88920.13150.054*
C30.7623 (2)0.7471 (2)0.10091 (12)0.0554 (7)
H30.81410.70400.11410.067*
C40.6855 (3)0.7010 (2)0.07095 (12)0.0610 (8)
H40.68630.62680.06340.073*
C50.6076 (3)0.7635 (2)0.05212 (11)0.0599 (8)
H50.55570.73150.03220.072*
C60.6066 (2)0.8745 (2)0.06290 (11)0.0510 (7)
H60.55340.91650.05060.061*
C70.56283 (17)1.0923 (2)0.12487 (9)0.0362 (5)
C80.5409 (2)1.0592 (2)0.17539 (10)0.0462 (6)
H80.58951.03060.19900.055*
C90.4474 (2)1.0688 (3)0.19044 (12)0.0604 (8)
H90.43281.04580.22400.073*
C100.3754 (2)1.1122 (3)0.15611 (14)0.0712 (10)
H100.31251.11900.16670.085*
C110.3960 (2)1.1453 (3)0.10667 (15)0.0717 (10)
H110.34701.17480.08360.086*
C120.4896 (2)1.1353 (3)0.09050 (12)0.0549 (7)
H120.50311.15750.05660.066*
C130.69171 (17)1.1375 (2)0.04289 (10)0.0402 (5)
C140.6807 (2)1.0852 (3)0.00577 (11)0.0581 (7)
H140.66841.01050.00720.070*
C150.6881 (3)1.1437 (3)0.05288 (12)0.0718 (10)
H150.68021.10780.08540.086*
C160.7066 (2)1.2523 (3)0.05154 (13)0.0679 (9)
H160.71161.29060.08300.082*
C170.7178 (3)1.3057 (3)0.00382 (14)0.0714 (9)
H170.72961.38040.00300.086*
C180.7116 (2)1.2486 (2)0.04340 (12)0.0547 (7)
H180.72081.28520.07570.066*
C191.02417 (18)1.1280 (2)0.09599 (10)0.0417 (5)
C200.9506 (2)1.1355 (4)0.05733 (12)0.0743 (11)
H200.88701.12490.06620.089*
C210.9671 (3)1.1584 (5)0.00530 (13)0.1017 (17)
H210.91501.16300.02030.122*
C221.0593 (2)1.1744 (4)0.00861 (12)0.0747 (10)
H221.07081.19110.04350.090*
C231.1335 (3)1.1656 (4)0.02877 (14)0.0954 (15)
H231.19701.17540.01950.115*
C241.1168 (2)1.1423 (4)0.08089 (13)0.0902 (15)
H241.16931.13610.10610.108*
C251.01384 (17)0.9537 (2)0.17303 (10)0.0408 (5)
C260.9726 (2)0.9045 (3)0.21528 (12)0.0575 (7)
H260.94340.94730.24000.069*
C270.9744 (2)0.7918 (3)0.22113 (15)0.0693 (9)
H270.94730.75980.25000.083*
C281.0161 (2)0.7276 (3)0.18456 (14)0.0668 (9)
H281.01540.65200.18790.080*
C291.0590 (3)0.7757 (3)0.14282 (13)0.0670 (9)
H291.08860.73250.11840.080*
C301.0580 (2)0.8881 (2)0.13729 (11)0.0538 (7)
H301.08750.92000.10920.065*
C311.09295 (18)1.1680 (2)0.20333 (10)0.0444 (6)
C321.1509 (2)1.1166 (3)0.24300 (11)0.0517 (7)
H321.14241.04280.24980.062*
C331.2219 (2)1.1761 (3)0.27261 (13)0.0681 (9)
H331.25981.14200.29990.082*
C341.2366 (3)1.2835 (3)0.26212 (15)0.0785 (11)
H341.28561.32180.28150.094*
C351.1795 (3)1.3353 (3)0.22308 (17)0.0797 (11)
H351.18901.40900.21620.096*
C361.1079 (2)1.2776 (3)0.19408 (14)0.0671 (9)
H361.06901.31320.16780.081*
C370.83280 (18)1.00119 (18)0.32193 (9)0.0360 (5)
C380.9007 (2)0.9489 (2)0.35648 (11)0.0507 (7)
H380.88700.87940.36870.061*
C390.9880 (2)0.9975 (3)0.37310 (13)0.0625 (8)
C401.0055 (2)1.1013 (2)0.35416 (12)0.0543 (7)
H401.06421.13490.36490.065*
C410.93999 (19)1.1572 (2)0.32017 (10)0.0403 (5)
C420.85182 (17)1.10647 (18)0.30314 (8)0.0333 (5)
C431.0621 (3)0.9410 (4)0.4119 (2)0.120 (2)
H43A1.02870.90310.43840.180*
H43B1.10490.99460.42880.180*
H43C1.09940.88990.39300.180*
C440.9608 (2)1.2719 (2)0.30369 (12)0.0501 (6)
H44A0.94561.27950.26610.075*
H44B1.02831.28800.31210.075*
H44C0.92161.32160.32230.075*
C451.0471 (7)1.4892 (5)0.0828 (3)0.134 (2)
C460.9466 (5)1.4605 (6)0.0753 (2)0.152 (3)
H46A0.91111.51890.05750.227*
H46B0.92151.44770.10920.227*
H46C0.93971.39540.05410.227*
N10.78530 (16)1.15978 (16)0.26594 (8)0.0348 (4)
N21.1273 (6)1.5132 (6)0.0876 (4)0.204 (3)
O10.73360 (15)0.90495 (15)0.24511 (7)0.0498 (4)
O20.71669 (16)0.83858 (15)0.33439 (8)0.0563 (5)
O30.64498 (14)1.01177 (15)0.30577 (8)0.0535 (5)
S10.72303 (5)0.93324 (5)0.30021 (2)0.03896 (14)
P10.99383 (4)1.10000 (6)0.16382 (2)0.03733 (14)
P20.68730 (4)1.06931 (5)0.10741 (2)0.03495 (13)
H1B0.7286 (14)1.142 (2)0.2687 (11)0.044 (8)*
H1A0.8049 (13)1.2294 (15)0.2671 (11)0.053 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ag10.03310 (10)0.04632 (12)0.03491 (10)0.00240 (8)0.00002 (7)0.00437 (7)
C10.0399 (13)0.0437 (13)0.0314 (12)0.0014 (11)0.0040 (9)0.0043 (9)
C20.0401 (14)0.0495 (15)0.0460 (14)0.0029 (11)0.0072 (11)0.0005 (11)
C30.0609 (19)0.0484 (16)0.0590 (17)0.0126 (14)0.0167 (14)0.0079 (13)
C40.089 (2)0.0398 (15)0.0565 (17)0.0039 (16)0.0201 (16)0.0014 (13)
C50.078 (2)0.0503 (17)0.0503 (16)0.0165 (16)0.0018 (15)0.0045 (13)
C60.0549 (17)0.0496 (16)0.0466 (15)0.0044 (13)0.0089 (12)0.0029 (12)
C70.0316 (12)0.0376 (12)0.0391 (13)0.0010 (9)0.0013 (9)0.0069 (9)
C80.0476 (15)0.0488 (15)0.0422 (14)0.0012 (12)0.0039 (11)0.0049 (11)
C90.0576 (19)0.073 (2)0.0532 (17)0.0070 (16)0.0186 (14)0.0091 (14)
C100.0382 (16)0.098 (3)0.079 (2)0.0005 (17)0.0159 (15)0.0185 (19)
C110.0372 (16)0.099 (3)0.077 (2)0.0131 (17)0.0027 (15)0.0028 (19)
C120.0375 (14)0.074 (2)0.0520 (16)0.0047 (14)0.0032 (12)0.0066 (14)
C130.0315 (12)0.0511 (15)0.0376 (13)0.0001 (11)0.0003 (9)0.0004 (10)
C140.071 (2)0.0616 (18)0.0406 (15)0.0094 (16)0.0008 (13)0.0016 (13)
C150.084 (3)0.094 (3)0.0366 (16)0.006 (2)0.0003 (15)0.0019 (15)
C160.061 (2)0.089 (3)0.0532 (18)0.0060 (18)0.0019 (14)0.0264 (17)
C170.083 (2)0.057 (2)0.075 (2)0.0048 (17)0.0060 (18)0.0206 (17)
C180.0634 (19)0.0510 (16)0.0500 (16)0.0028 (14)0.0056 (13)0.0025 (12)
C190.0322 (12)0.0544 (15)0.0388 (13)0.0037 (11)0.0040 (10)0.0020 (11)
C200.0343 (15)0.149 (4)0.0397 (16)0.0009 (18)0.0041 (12)0.0065 (18)
C210.050 (2)0.216 (5)0.0391 (17)0.012 (3)0.0029 (14)0.014 (2)
C220.0552 (19)0.130 (3)0.0398 (16)0.003 (2)0.0096 (14)0.0117 (18)
C230.0424 (18)0.189 (5)0.057 (2)0.014 (2)0.0133 (15)0.020 (2)
C240.0335 (16)0.187 (5)0.0500 (18)0.010 (2)0.0003 (13)0.027 (2)
C250.0310 (12)0.0510 (15)0.0395 (13)0.0027 (11)0.0025 (9)0.0018 (10)
C260.0514 (17)0.0591 (18)0.0637 (18)0.0077 (14)0.0170 (14)0.0090 (14)
C270.061 (2)0.062 (2)0.086 (2)0.0031 (16)0.0159 (17)0.0233 (17)
C280.063 (2)0.0486 (18)0.085 (2)0.0063 (15)0.0188 (17)0.0062 (16)
C290.083 (2)0.062 (2)0.0531 (18)0.0226 (17)0.0129 (16)0.0089 (15)
C300.0612 (18)0.0606 (18)0.0391 (14)0.0126 (14)0.0018 (12)0.0013 (12)
C310.0325 (13)0.0571 (16)0.0434 (14)0.0031 (11)0.0015 (10)0.0024 (11)
C320.0399 (15)0.0653 (18)0.0490 (15)0.0026 (13)0.0029 (11)0.0071 (13)
C330.0458 (17)0.094 (3)0.062 (2)0.0034 (17)0.0155 (14)0.0098 (18)
C340.055 (2)0.091 (3)0.087 (3)0.0170 (19)0.0126 (18)0.022 (2)
C350.068 (2)0.068 (2)0.100 (3)0.0246 (19)0.008 (2)0.001 (2)
C360.0587 (19)0.065 (2)0.075 (2)0.0126 (16)0.0134 (16)0.0073 (16)
C370.0434 (13)0.0307 (11)0.0336 (12)0.0012 (10)0.0013 (9)0.0005 (9)
C380.0621 (18)0.0366 (14)0.0516 (16)0.0045 (12)0.0089 (13)0.0096 (11)
C390.0626 (19)0.0511 (17)0.070 (2)0.0022 (14)0.0220 (15)0.0145 (14)
C400.0469 (16)0.0496 (16)0.0642 (18)0.0078 (13)0.0104 (13)0.0004 (13)
C410.0415 (14)0.0373 (13)0.0423 (13)0.0034 (10)0.0047 (10)0.0016 (10)
C420.0402 (13)0.0298 (11)0.0299 (11)0.0006 (9)0.0033 (9)0.0030 (8)
C430.103 (3)0.089 (3)0.157 (4)0.014 (3)0.073 (3)0.048 (3)
C440.0466 (15)0.0401 (14)0.0638 (17)0.0095 (12)0.0057 (13)0.0008 (12)
C450.183 (7)0.083 (4)0.144 (5)0.005 (5)0.062 (6)0.005 (3)
C460.159 (6)0.175 (7)0.127 (5)0.013 (5)0.054 (5)0.004 (4)
N10.0385 (12)0.0310 (10)0.0351 (10)0.0014 (9)0.0034 (8)0.0018 (8)
N20.206 (8)0.140 (6)0.274 (9)0.020 (6)0.072 (7)0.026 (5)
O10.0611 (12)0.0489 (11)0.0392 (10)0.0095 (9)0.0020 (8)0.0069 (8)
O20.0761 (14)0.0386 (10)0.0536 (11)0.0185 (10)0.0004 (10)0.0097 (8)
O30.0446 (11)0.0458 (11)0.0712 (13)0.0007 (9)0.0112 (9)0.0014 (9)
S10.0466 (3)0.0311 (3)0.0392 (3)0.0061 (2)0.0031 (2)0.0005 (2)
P10.0284 (3)0.0482 (4)0.0352 (3)0.0018 (3)0.0009 (2)0.0012 (3)
P20.0309 (3)0.0406 (3)0.0328 (3)0.0005 (2)0.0012 (2)0.0036 (2)
Geometric parameters (Å, º) top
Ag1—N12.393 (2)C25—C301.383 (4)
Ag1—P22.4955 (9)C25—P11.826 (3)
Ag1—P12.5005 (8)C26—C271.388 (5)
C1—C21.385 (4)C26—H260.9300
C1—C61.399 (4)C27—C281.372 (5)
C1—P21.828 (3)C27—H270.9300
C2—C31.386 (4)C28—C291.379 (5)
C2—H20.9300C28—H280.9300
C3—C41.374 (5)C29—C301.385 (4)
C3—H30.9300C29—H290.9300
C4—C51.374 (5)C30—H300.9300
C4—H40.9300C31—C321.384 (4)
C5—C61.386 (4)C31—C361.381 (4)
C5—H50.9300C31—P11.830 (3)
C6—H60.9300C32—C331.392 (4)
C7—C121.384 (4)C32—H320.9300
C7—C81.393 (3)C33—C341.361 (5)
C7—P21.825 (2)C33—H330.9300
C8—C91.376 (4)C34—C351.370 (5)
C8—H80.9300C34—H340.9300
C9—C101.374 (5)C35—C361.378 (4)
C9—H90.9300C35—H350.9300
C10—C111.362 (5)C36—H360.9300
C10—H100.9300C37—C381.387 (3)
C11—C121.388 (4)C37—C421.406 (3)
C11—H110.9300C37—S11.777 (2)
C12—H120.9300C38—C391.379 (4)
C13—C141.384 (4)C38—H380.9300
C13—C181.388 (4)C39—C401.386 (4)
C13—P21.836 (3)C39—C431.528 (4)
C14—C151.399 (4)C40—C411.380 (4)
C14—H140.9300C40—H400.9300
C15—C161.354 (5)C41—C421.403 (3)
C15—H150.9300C41—C441.499 (3)
C16—C171.369 (5)C42—N11.421 (3)
C16—H160.9300C43—H43A0.9600
C17—C181.390 (4)C43—H43B0.9600
C17—H170.9300C43—H43C0.9600
C18—H180.9300C44—H44A0.9600
C19—C201.356 (4)C44—H44B0.9600
C19—C241.371 (4)C44—H44C0.9600
C19—P11.825 (3)C45—N21.141 (10)
C20—C211.378 (4)C45—C461.428 (9)
C20—H200.9300C46—H46A0.9600
C21—C221.358 (5)C46—H46B0.9600
C21—H210.9300C46—H46C0.9600
C22—C231.343 (5)N1—H1B0.821 (17)
C22—H220.9300N1—H1A0.895 (16)
C23—C241.382 (5)O1—S11.4513 (18)
C23—H230.9300O2—S11.4522 (19)
C24—H240.9300O3—S11.458 (2)
C25—C261.384 (4)
N1—Ag1—P2121.82 (6)C29—C28—H28120.2
N1—Ag1—P1112.50 (6)C28—C29—C30120.1 (3)
P2—Ag1—P1122.09 (3)C28—C29—H29120.0
C2—C1—C6118.5 (2)C30—C29—H29120.0
C2—C1—P2119.46 (19)C25—C30—C29120.9 (3)
C6—C1—P2122.0 (2)C25—C30—H30119.6
C1—C2—C3120.9 (3)C29—C30—H30119.6
C1—C2—H2119.5C32—C31—C36118.6 (3)
C3—C2—H2119.5C32—C31—P1123.6 (2)
C4—C3—C2119.6 (3)C36—C31—P1117.8 (2)
C4—C3—H3120.2C31—C32—C33119.6 (3)
C2—C3—H3120.2C31—C32—H32120.2
C3—C4—C5120.7 (3)C33—C32—H32120.2
C3—C4—H4119.7C34—C33—C32120.7 (3)
C5—C4—H4119.7C34—C33—H33119.6
C4—C5—C6119.9 (3)C32—C33—H33119.6
C4—C5—H5120.1C33—C34—C35120.2 (3)
C6—C5—H5120.1C33—C34—H34119.9
C5—C6—C1120.3 (3)C35—C34—H34119.9
C5—C6—H6119.8C36—C35—C34119.6 (4)
C1—C6—H6119.8C36—C35—H35120.2
C12—C7—C8119.1 (2)C34—C35—H35120.2
C12—C7—P2124.2 (2)C35—C36—C31121.3 (3)
C8—C7—P2116.68 (19)C35—C36—H36119.4
C9—C8—C7120.0 (3)C31—C36—H36119.4
C9—C8—H8120.0C38—C37—C42120.1 (2)
C7—C8—H8120.0C38—C37—S1119.73 (19)
C8—C9—C10120.4 (3)C42—C37—S1120.12 (18)
C8—C9—H9119.8C39—C38—C37121.6 (2)
C10—C9—H9119.8C39—C38—H38119.2
C11—C10—C9120.2 (3)C37—C38—H38119.2
C11—C10—H10119.9C38—C39—C40117.5 (3)
C9—C10—H10119.9C38—C39—C43121.7 (3)
C10—C11—C12120.4 (3)C40—C39—C43120.8 (3)
C10—C11—H11119.8C41—C40—C39123.2 (3)
C12—C11—H11119.8C41—C40—H40118.4
C7—C12—C11119.9 (3)C39—C40—H40118.4
C7—C12—H12120.0C40—C41—C42118.8 (2)
C11—C12—H12120.0C40—C41—C44120.6 (2)
C14—C13—C18118.1 (3)C42—C41—C44120.6 (2)
C14—C13—P2124.6 (2)C37—C42—C41118.8 (2)
C18—C13—P2117.3 (2)C37—C42—N1121.2 (2)
C13—C14—C15120.4 (3)C41—C42—N1120.0 (2)
C13—C14—H14119.8C39—C43—H43A109.5
C15—C14—H14119.8C39—C43—H43B109.5
C16—C15—C14120.5 (3)H43A—C43—H43B109.5
C16—C15—H15119.7C39—C43—H43C109.5
C14—C15—H15119.7H43A—C43—H43C109.5
C15—C16—C17120.0 (3)H43B—C43—H43C109.5
C15—C16—H16120.0C41—C44—H44A109.5
C17—C16—H16120.0C41—C44—H44B109.5
C16—C17—C18120.3 (3)H44A—C44—H44B109.5
C16—C17—H17119.9C41—C44—H44C109.5
C18—C17—H17119.9H44A—C44—H44C109.5
C13—C18—C17120.7 (3)H44B—C44—H44C109.5
C13—C18—H18119.7N2—C45—C46178.5 (10)
C17—C18—H18119.7C45—C46—H46A109.5
C20—C19—C24116.9 (3)C45—C46—H46B109.5
C20—C19—P1118.4 (2)H46A—C46—H46B109.5
C24—C19—P1124.7 (2)C45—C46—H46C109.5
C19—C20—C21122.1 (3)H46A—C46—H46C109.5
C19—C20—H20118.9H46B—C46—H46C109.5
C21—C20—H20118.9C42—N1—Ag1114.06 (14)
C22—C21—C20120.0 (3)C42—N1—H1B113 (2)
C22—C21—H21120.0Ag1—N1—H1B107 (2)
C20—C21—H21120.0C42—N1—H1A103.8 (16)
C23—C22—C21119.0 (3)Ag1—N1—H1A95.6 (18)
C23—C22—H22120.5H1B—N1—H1A123 (2)
C21—C22—H22120.5O1—S1—O2113.17 (12)
C22—C23—C24120.9 (3)O1—S1—O3112.21 (12)
C22—C23—H23119.6O2—S1—O3113.08 (13)
C24—C23—H23119.6O1—S1—C37105.25 (11)
C19—C24—C23121.1 (3)O2—S1—C37106.19 (12)
C19—C24—H24119.5O3—S1—C37106.16 (11)
C23—C24—H24119.5C19—P1—C25105.11 (12)
C26—C25—C30118.4 (3)C19—P1—C31102.19 (12)
C26—C25—P1117.3 (2)C25—P1—C31106.17 (12)
C30—C25—P1123.9 (2)C19—P1—Ag1111.92 (9)
C25—C26—C27120.7 (3)C25—P1—Ag1105.71 (8)
C25—C26—H26119.7C31—P1—Ag1124.26 (9)
C27—C26—H26119.7C7—P2—C1101.65 (11)
C28—C27—C26120.3 (3)C7—P2—C13103.80 (11)
C28—C27—H27119.9C1—P2—C13105.01 (11)
C26—C27—H27119.9C7—P2—Ag1115.28 (8)
C27—C28—C29119.6 (3)C1—P2—Ag1115.90 (8)
C27—C28—H28120.2C13—P2—Ag1113.67 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.90 (2)2.23 (2)3.026 (3)148 (2)
N1—H1B···O30.82 (2)2.21 (2)2.887 (3)139 (2)
Symmetry code: (i) x+3/2, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula[Ag(C8H10NO3S)(C18H15P)2]·C2H3N
Mr873.69
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)13.782 (3), 12.252 (3), 25.243 (5)
β (°) 94.32 (3)
V3)4250.5 (15)
Z4
Radiation typeMo Kα
µ (mm1)0.64
Crystal size (mm)0.26 × 0.21 × 0.18
Data collection
DiffractometerRigaku R-AXIS RAPID
Absorption correctionMulti-scan
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.841, 0.892
No. of measured, independent and
observed [I > 2σ(I)] reflections
39847, 9612, 7595
Rint0.047
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.092, 0.84
No. of reflections9612
No. of parameters506
No. of restraints3
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.45, 0.45

Computer programs: PROCESS-AUTO (Rigaku, 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Sheldrick, 1990).

Selected geometric parameters (Å, º) top
Ag1—N12.393 (2)Ag1—P12.5005 (8)
Ag1—P22.4955 (9)
N1—Ag1—P2121.82 (6)P2—Ag1—P1122.09 (3)
N1—Ag1—P1112.50 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.895 (16)2.23 (2)3.026 (3)147.8 (18)
N1—H1B···O30.821 (17)2.21 (2)2.887 (3)139 (2)
Symmetry code: (i) x+3/2, y+1/2, z+1/2.
 

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