Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807048076/hb2567sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807048076/hb2567Isup2.hkl |
CCDC reference: 667108
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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.
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).
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).
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 (I), with displacement ellipsoids drawn at the 30% probability level (H atoms omitted for clarity). |
[Ag(C8H10NO3S)(C18H15P)2]·C2H3N | F(000) = 1800 |
Mr = 873.69 | Dx = 1.365 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 28308 reflections |
a = 13.782 (3) Å | θ = 3.0–27.5° |
b = 12.252 (3) Å | µ = 0.64 mm−1 |
c = 25.243 (5) Å | T = 293 K |
β = 94.32 (3)° | Block, colorless |
V = 4250.5 (15) Å3 | 0.26 × 0.21 × 0.18 mm |
Z = 4 |
Rigaku R-AXIS RAPID diffractometer | 9612 independent reflections |
Radiation source: rotating anode | 7595 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.047 |
Detector resolution: 10.0 pixels mm-1 | θmax = 27.5°, θmin = 3.2° |
ω scans | h = −17→17 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −15→15 |
Tmin = 0.841, Tmax = 0.892 | l = −32→32 |
39847 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)] = 0.034 | Hydrogen site location: difmap and geom |
wR(F2) = 0.092 | H 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 parameters | Δρmax = 0.45 e Å−3 |
3 restraints | Δρmin = −0.45 e Å−3 |
[Ag(C8H10NO3S)(C18H15P)2]·C2H3N | V = 4250.5 (15) Å3 |
Mr = 873.69 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 13.782 (3) Å | µ = 0.64 mm−1 |
b = 12.252 (3) Å | T = 293 K |
c = 25.243 (5) Å | 0.26 × 0.21 × 0.18 mm |
β = 94.32 (3)° |
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 = 0.892 | Rint = 0.047 |
39847 measured reflections |
R[F2 > 2σ(F2)] = 0.034 | 3 restraints |
wR(F2) = 0.092 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.84 | Δρmax = 0.45 e Å−3 |
9612 reflections | Δρmin = −0.45 e Å−3 |
506 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 | 0.817193 (13) | 1.130397 (16) | 0.175155 (7) | 0.03824 (7) | |
C1 | 0.68522 (18) | 0.9235 (2) | 0.09214 (9) | 0.0382 (5) | |
C2 | 0.76198 (19) | 0.8582 (2) | 0.11134 (10) | 0.0450 (6) | |
H2 | 0.8141 | 0.8892 | 0.1315 | 0.054* | |
C3 | 0.7623 (2) | 0.7471 (2) | 0.10091 (12) | 0.0554 (7) | |
H3 | 0.8141 | 0.7040 | 0.1141 | 0.067* | |
C4 | 0.6855 (3) | 0.7010 (2) | 0.07095 (12) | 0.0610 (8) | |
H4 | 0.6863 | 0.6268 | 0.0634 | 0.073* | |
C5 | 0.6076 (3) | 0.7635 (2) | 0.05212 (11) | 0.0599 (8) | |
H5 | 0.5557 | 0.7315 | 0.0322 | 0.072* | |
C6 | 0.6066 (2) | 0.8745 (2) | 0.06290 (11) | 0.0510 (7) | |
H6 | 0.5534 | 0.9165 | 0.0506 | 0.061* | |
C7 | 0.56283 (17) | 1.0923 (2) | 0.12487 (9) | 0.0362 (5) | |
C8 | 0.5409 (2) | 1.0592 (2) | 0.17539 (10) | 0.0462 (6) | |
H8 | 0.5895 | 1.0306 | 0.1990 | 0.055* | |
C9 | 0.4474 (2) | 1.0688 (3) | 0.19044 (12) | 0.0604 (8) | |
H9 | 0.4328 | 1.0458 | 0.2240 | 0.073* | |
C10 | 0.3754 (2) | 1.1122 (3) | 0.15611 (14) | 0.0712 (10) | |
H10 | 0.3125 | 1.1190 | 0.1667 | 0.085* | |
C11 | 0.3960 (2) | 1.1453 (3) | 0.10667 (15) | 0.0717 (10) | |
H11 | 0.3470 | 1.1748 | 0.0836 | 0.086* | |
C12 | 0.4896 (2) | 1.1353 (3) | 0.09050 (12) | 0.0549 (7) | |
H12 | 0.5031 | 1.1575 | 0.0566 | 0.066* | |
C13 | 0.69171 (17) | 1.1375 (2) | 0.04289 (10) | 0.0402 (5) | |
C14 | 0.6807 (2) | 1.0852 (3) | −0.00577 (11) | 0.0581 (7) | |
H14 | 0.6684 | 1.0105 | −0.0072 | 0.070* | |
C15 | 0.6881 (3) | 1.1437 (3) | −0.05288 (12) | 0.0718 (10) | |
H15 | 0.6802 | 1.1078 | −0.0854 | 0.086* | |
C16 | 0.7066 (2) | 1.2523 (3) | −0.05154 (13) | 0.0679 (9) | |
H16 | 0.7116 | 1.2906 | −0.0830 | 0.082* | |
C17 | 0.7178 (3) | 1.3057 (3) | −0.00382 (14) | 0.0714 (9) | |
H17 | 0.7296 | 1.3804 | −0.0030 | 0.086* | |
C18 | 0.7116 (2) | 1.2486 (2) | 0.04340 (12) | 0.0547 (7) | |
H18 | 0.7208 | 1.2852 | 0.0757 | 0.066* | |
C19 | 1.02417 (18) | 1.1280 (2) | 0.09599 (10) | 0.0417 (5) | |
C20 | 0.9506 (2) | 1.1355 (4) | 0.05733 (12) | 0.0743 (11) | |
H20 | 0.8870 | 1.1249 | 0.0662 | 0.089* | |
C21 | 0.9671 (3) | 1.1584 (5) | 0.00530 (13) | 0.1017 (17) | |
H21 | 0.9150 | 1.1630 | −0.0203 | 0.122* | |
C22 | 1.0593 (2) | 1.1744 (4) | −0.00861 (12) | 0.0747 (10) | |
H22 | 1.0708 | 1.1911 | −0.0435 | 0.090* | |
C23 | 1.1335 (3) | 1.1656 (4) | 0.02877 (14) | 0.0954 (15) | |
H23 | 1.1970 | 1.1754 | 0.0195 | 0.115* | |
C24 | 1.1168 (2) | 1.1423 (4) | 0.08089 (13) | 0.0902 (15) | |
H24 | 1.1693 | 1.1361 | 0.1061 | 0.108* | |
C25 | 1.01384 (17) | 0.9537 (2) | 0.17303 (10) | 0.0408 (5) | |
C26 | 0.9726 (2) | 0.9045 (3) | 0.21528 (12) | 0.0575 (7) | |
H26 | 0.9434 | 0.9473 | 0.2400 | 0.069* | |
C27 | 0.9744 (2) | 0.7918 (3) | 0.22113 (15) | 0.0693 (9) | |
H27 | 0.9473 | 0.7598 | 0.2500 | 0.083* | |
C28 | 1.0161 (2) | 0.7276 (3) | 0.18456 (14) | 0.0668 (9) | |
H28 | 1.0154 | 0.6520 | 0.1879 | 0.080* | |
C29 | 1.0590 (3) | 0.7757 (3) | 0.14282 (13) | 0.0670 (9) | |
H29 | 1.0886 | 0.7325 | 0.1184 | 0.080* | |
C30 | 1.0580 (2) | 0.8881 (2) | 0.13729 (11) | 0.0538 (7) | |
H30 | 1.0875 | 0.9200 | 0.1092 | 0.065* | |
C31 | 1.09295 (18) | 1.1680 (2) | 0.20333 (10) | 0.0444 (6) | |
C32 | 1.1509 (2) | 1.1166 (3) | 0.24300 (11) | 0.0517 (7) | |
H32 | 1.1424 | 1.0428 | 0.2498 | 0.062* | |
C33 | 1.2219 (2) | 1.1761 (3) | 0.27261 (13) | 0.0681 (9) | |
H33 | 1.2598 | 1.1420 | 0.2999 | 0.082* | |
C34 | 1.2366 (3) | 1.2835 (3) | 0.26212 (15) | 0.0785 (11) | |
H34 | 1.2856 | 1.3218 | 0.2815 | 0.094* | |
C35 | 1.1795 (3) | 1.3353 (3) | 0.22308 (17) | 0.0797 (11) | |
H35 | 1.1890 | 1.4090 | 0.2162 | 0.096* | |
C36 | 1.1079 (2) | 1.2776 (3) | 0.19408 (14) | 0.0671 (9) | |
H36 | 1.0690 | 1.3132 | 0.1678 | 0.081* | |
C37 | 0.83280 (18) | 1.00119 (18) | 0.32193 (9) | 0.0360 (5) | |
C38 | 0.9007 (2) | 0.9489 (2) | 0.35648 (11) | 0.0507 (7) | |
H38 | 0.8870 | 0.8794 | 0.3687 | 0.061* | |
C39 | 0.9880 (2) | 0.9975 (3) | 0.37310 (13) | 0.0625 (8) | |
C40 | 1.0055 (2) | 1.1013 (2) | 0.35416 (12) | 0.0543 (7) | |
H40 | 1.0642 | 1.1349 | 0.3649 | 0.065* | |
C41 | 0.93999 (19) | 1.1572 (2) | 0.32017 (10) | 0.0403 (5) | |
C42 | 0.85182 (17) | 1.10647 (18) | 0.30314 (8) | 0.0333 (5) | |
C43 | 1.0621 (3) | 0.9410 (4) | 0.4119 (2) | 0.120 (2) | |
H43A | 1.0287 | 0.9031 | 0.4384 | 0.180* | |
H43B | 1.1049 | 0.9946 | 0.4288 | 0.180* | |
H43C | 1.0994 | 0.8899 | 0.3930 | 0.180* | |
C44 | 0.9608 (2) | 1.2719 (2) | 0.30369 (12) | 0.0501 (6) | |
H44A | 0.9456 | 1.2795 | 0.2661 | 0.075* | |
H44B | 1.0283 | 1.2880 | 0.3121 | 0.075* | |
H44C | 0.9216 | 1.3216 | 0.3223 | 0.075* | |
C45 | 1.0471 (7) | 1.4892 (5) | 0.0828 (3) | 0.134 (2) | |
C46 | 0.9466 (5) | 1.4605 (6) | 0.0753 (2) | 0.152 (3) | |
H46A | 0.9111 | 1.5189 | 0.0575 | 0.227* | |
H46B | 0.9215 | 1.4477 | 0.1092 | 0.227* | |
H46C | 0.9397 | 1.3954 | 0.0541 | 0.227* | |
N1 | 0.78530 (16) | 1.15978 (16) | 0.26594 (8) | 0.0348 (4) | |
N2 | 1.1273 (6) | 1.5132 (6) | 0.0876 (4) | 0.204 (3) | |
O1 | 0.73360 (15) | 0.90495 (15) | 0.24511 (7) | 0.0498 (4) | |
O2 | 0.71669 (16) | 0.83858 (15) | 0.33439 (8) | 0.0563 (5) | |
O3 | 0.64498 (14) | 1.01177 (15) | 0.30577 (8) | 0.0535 (5) | |
S1 | 0.72303 (5) | 0.93324 (5) | 0.30021 (2) | 0.03896 (14) | |
P1 | 0.99383 (4) | 1.10000 (6) | 0.16382 (2) | 0.03733 (14) | |
P2 | 0.68730 (4) | 1.06931 (5) | 0.10741 (2) | 0.03495 (13) | |
H1B | 0.7286 (14) | 1.142 (2) | 0.2687 (11) | 0.044 (8)* | |
H1A | 0.8049 (13) | 1.2294 (15) | 0.2671 (11) | 0.053 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ag1 | 0.03310 (10) | 0.04632 (12) | 0.03491 (10) | 0.00240 (8) | 0.00002 (7) | −0.00437 (7) |
C1 | 0.0399 (13) | 0.0437 (13) | 0.0314 (12) | −0.0014 (11) | 0.0040 (9) | −0.0043 (9) |
C2 | 0.0401 (14) | 0.0495 (15) | 0.0460 (14) | 0.0029 (11) | 0.0072 (11) | −0.0005 (11) |
C3 | 0.0609 (19) | 0.0484 (16) | 0.0590 (17) | 0.0126 (14) | 0.0167 (14) | 0.0079 (13) |
C4 | 0.089 (2) | 0.0398 (15) | 0.0565 (17) | −0.0039 (16) | 0.0201 (16) | −0.0014 (13) |
C5 | 0.078 (2) | 0.0503 (17) | 0.0503 (16) | −0.0165 (16) | −0.0018 (15) | −0.0045 (13) |
C6 | 0.0549 (17) | 0.0496 (16) | 0.0466 (15) | −0.0044 (13) | −0.0089 (12) | −0.0029 (12) |
C7 | 0.0316 (12) | 0.0376 (12) | 0.0391 (13) | −0.0010 (9) | 0.0013 (9) | −0.0069 (9) |
C8 | 0.0476 (15) | 0.0488 (15) | 0.0422 (14) | 0.0012 (12) | 0.0039 (11) | −0.0049 (11) |
C9 | 0.0576 (19) | 0.073 (2) | 0.0532 (17) | −0.0070 (16) | 0.0186 (14) | −0.0091 (14) |
C10 | 0.0382 (16) | 0.098 (3) | 0.079 (2) | −0.0005 (17) | 0.0159 (15) | −0.0185 (19) |
C11 | 0.0372 (16) | 0.099 (3) | 0.077 (2) | 0.0131 (17) | −0.0027 (15) | 0.0028 (19) |
C12 | 0.0375 (14) | 0.074 (2) | 0.0520 (16) | 0.0047 (14) | −0.0032 (12) | 0.0066 (14) |
C13 | 0.0315 (12) | 0.0511 (15) | 0.0376 (13) | −0.0001 (11) | 0.0003 (9) | 0.0004 (10) |
C14 | 0.071 (2) | 0.0616 (18) | 0.0406 (15) | −0.0094 (16) | −0.0008 (13) | −0.0016 (13) |
C15 | 0.084 (3) | 0.094 (3) | 0.0366 (16) | −0.006 (2) | 0.0003 (15) | 0.0019 (15) |
C16 | 0.061 (2) | 0.089 (3) | 0.0532 (18) | 0.0060 (18) | 0.0019 (14) | 0.0264 (17) |
C17 | 0.083 (2) | 0.057 (2) | 0.075 (2) | 0.0048 (17) | 0.0060 (18) | 0.0206 (17) |
C18 | 0.0634 (19) | 0.0510 (16) | 0.0500 (16) | 0.0028 (14) | 0.0056 (13) | 0.0025 (12) |
C19 | 0.0322 (12) | 0.0544 (15) | 0.0388 (13) | 0.0037 (11) | 0.0040 (10) | 0.0020 (11) |
C20 | 0.0343 (15) | 0.149 (4) | 0.0397 (16) | 0.0009 (18) | 0.0041 (12) | 0.0065 (18) |
C21 | 0.050 (2) | 0.216 (5) | 0.0391 (17) | 0.012 (3) | 0.0029 (14) | 0.014 (2) |
C22 | 0.0552 (19) | 0.130 (3) | 0.0398 (16) | 0.003 (2) | 0.0096 (14) | 0.0117 (18) |
C23 | 0.0424 (18) | 0.189 (5) | 0.057 (2) | −0.014 (2) | 0.0133 (15) | 0.020 (2) |
C24 | 0.0335 (16) | 0.187 (5) | 0.0500 (18) | −0.010 (2) | 0.0003 (13) | 0.027 (2) |
C25 | 0.0310 (12) | 0.0510 (15) | 0.0395 (13) | 0.0027 (11) | −0.0025 (9) | 0.0018 (10) |
C26 | 0.0514 (17) | 0.0591 (18) | 0.0637 (18) | 0.0077 (14) | 0.0170 (14) | 0.0090 (14) |
C27 | 0.061 (2) | 0.062 (2) | 0.086 (2) | 0.0031 (16) | 0.0159 (17) | 0.0233 (17) |
C28 | 0.063 (2) | 0.0486 (18) | 0.085 (2) | 0.0063 (15) | −0.0188 (17) | 0.0062 (16) |
C29 | 0.083 (2) | 0.062 (2) | 0.0531 (18) | 0.0226 (17) | −0.0129 (16) | −0.0089 (15) |
C30 | 0.0612 (18) | 0.0606 (18) | 0.0391 (14) | 0.0126 (14) | 0.0018 (12) | −0.0013 (12) |
C31 | 0.0325 (13) | 0.0571 (16) | 0.0434 (14) | −0.0031 (11) | 0.0015 (10) | −0.0024 (11) |
C32 | 0.0399 (15) | 0.0653 (18) | 0.0490 (15) | 0.0026 (13) | −0.0029 (11) | −0.0071 (13) |
C33 | 0.0458 (17) | 0.094 (3) | 0.062 (2) | 0.0034 (17) | −0.0155 (14) | −0.0098 (18) |
C34 | 0.055 (2) | 0.091 (3) | 0.087 (3) | −0.0170 (19) | −0.0126 (18) | −0.022 (2) |
C35 | 0.068 (2) | 0.068 (2) | 0.100 (3) | −0.0246 (19) | −0.008 (2) | −0.001 (2) |
C36 | 0.0587 (19) | 0.065 (2) | 0.075 (2) | −0.0126 (16) | −0.0134 (16) | 0.0073 (16) |
C37 | 0.0434 (13) | 0.0307 (11) | 0.0336 (12) | −0.0012 (10) | 0.0013 (9) | −0.0005 (9) |
C38 | 0.0621 (18) | 0.0366 (14) | 0.0516 (16) | −0.0045 (12) | −0.0089 (13) | 0.0096 (11) |
C39 | 0.0626 (19) | 0.0511 (17) | 0.070 (2) | −0.0022 (14) | −0.0220 (15) | 0.0145 (14) |
C40 | 0.0469 (16) | 0.0496 (16) | 0.0642 (18) | −0.0078 (13) | −0.0104 (13) | −0.0004 (13) |
C41 | 0.0415 (14) | 0.0373 (13) | 0.0423 (13) | −0.0034 (10) | 0.0047 (10) | −0.0016 (10) |
C42 | 0.0402 (13) | 0.0298 (11) | 0.0299 (11) | −0.0006 (9) | 0.0033 (9) | −0.0030 (8) |
C43 | 0.103 (3) | 0.089 (3) | 0.157 (4) | −0.014 (3) | −0.073 (3) | 0.048 (3) |
C44 | 0.0466 (15) | 0.0401 (14) | 0.0638 (17) | −0.0095 (12) | 0.0057 (13) | −0.0008 (12) |
C45 | 0.183 (7) | 0.083 (4) | 0.144 (5) | 0.005 (5) | 0.062 (6) | 0.005 (3) |
C46 | 0.159 (6) | 0.175 (7) | 0.127 (5) | −0.013 (5) | 0.054 (5) | −0.004 (4) |
N1 | 0.0385 (12) | 0.0310 (10) | 0.0351 (10) | −0.0014 (9) | 0.0034 (8) | 0.0018 (8) |
N2 | 0.206 (8) | 0.140 (6) | 0.274 (9) | −0.020 (6) | 0.072 (7) | 0.026 (5) |
O1 | 0.0611 (12) | 0.0489 (11) | 0.0392 (10) | −0.0095 (9) | 0.0020 (8) | −0.0069 (8) |
O2 | 0.0761 (14) | 0.0386 (10) | 0.0536 (11) | −0.0185 (10) | 0.0004 (10) | 0.0097 (8) |
O3 | 0.0446 (11) | 0.0458 (11) | 0.0712 (13) | −0.0007 (9) | 0.0112 (9) | −0.0014 (9) |
S1 | 0.0466 (3) | 0.0311 (3) | 0.0392 (3) | −0.0061 (2) | 0.0031 (2) | −0.0005 (2) |
P1 | 0.0284 (3) | 0.0482 (4) | 0.0352 (3) | 0.0018 (3) | 0.0009 (2) | 0.0012 (3) |
P2 | 0.0309 (3) | 0.0406 (3) | 0.0328 (3) | 0.0005 (2) | −0.0012 (2) | −0.0036 (2) |
Ag1—N1 | 2.393 (2) | C25—C30 | 1.383 (4) |
Ag1—P2 | 2.4955 (9) | C25—P1 | 1.826 (3) |
Ag1—P1 | 2.5005 (8) | C26—C27 | 1.388 (5) |
C1—C2 | 1.385 (4) | C26—H26 | 0.9300 |
C1—C6 | 1.399 (4) | C27—C28 | 1.372 (5) |
C1—P2 | 1.828 (3) | C27—H27 | 0.9300 |
C2—C3 | 1.386 (4) | C28—C29 | 1.379 (5) |
C2—H2 | 0.9300 | C28—H28 | 0.9300 |
C3—C4 | 1.374 (5) | C29—C30 | 1.385 (4) |
C3—H3 | 0.9300 | C29—H29 | 0.9300 |
C4—C5 | 1.374 (5) | C30—H30 | 0.9300 |
C4—H4 | 0.9300 | C31—C32 | 1.384 (4) |
C5—C6 | 1.386 (4) | C31—C36 | 1.381 (4) |
C5—H5 | 0.9300 | C31—P1 | 1.830 (3) |
C6—H6 | 0.9300 | C32—C33 | 1.392 (4) |
C7—C12 | 1.384 (4) | C32—H32 | 0.9300 |
C7—C8 | 1.393 (3) | C33—C34 | 1.361 (5) |
C7—P2 | 1.825 (2) | C33—H33 | 0.9300 |
C8—C9 | 1.376 (4) | C34—C35 | 1.370 (5) |
C8—H8 | 0.9300 | C34—H34 | 0.9300 |
C9—C10 | 1.374 (5) | C35—C36 | 1.378 (4) |
C9—H9 | 0.9300 | C35—H35 | 0.9300 |
C10—C11 | 1.362 (5) | C36—H36 | 0.9300 |
C10—H10 | 0.9300 | C37—C38 | 1.387 (3) |
C11—C12 | 1.388 (4) | C37—C42 | 1.406 (3) |
C11—H11 | 0.9300 | C37—S1 | 1.777 (2) |
C12—H12 | 0.9300 | C38—C39 | 1.379 (4) |
C13—C14 | 1.384 (4) | C38—H38 | 0.9300 |
C13—C18 | 1.388 (4) | C39—C40 | 1.386 (4) |
C13—P2 | 1.836 (3) | C39—C43 | 1.528 (4) |
C14—C15 | 1.399 (4) | C40—C41 | 1.380 (4) |
C14—H14 | 0.9300 | C40—H40 | 0.9300 |
C15—C16 | 1.354 (5) | C41—C42 | 1.403 (3) |
C15—H15 | 0.9300 | C41—C44 | 1.499 (3) |
C16—C17 | 1.369 (5) | C42—N1 | 1.421 (3) |
C16—H16 | 0.9300 | C43—H43A | 0.9600 |
C17—C18 | 1.390 (4) | C43—H43B | 0.9600 |
C17—H17 | 0.9300 | C43—H43C | 0.9600 |
C18—H18 | 0.9300 | C44—H44A | 0.9600 |
C19—C20 | 1.356 (4) | C44—H44B | 0.9600 |
C19—C24 | 1.371 (4) | C44—H44C | 0.9600 |
C19—P1 | 1.825 (3) | C45—N2 | 1.141 (10) |
C20—C21 | 1.378 (4) | C45—C46 | 1.428 (9) |
C20—H20 | 0.9300 | C46—H46A | 0.9600 |
C21—C22 | 1.358 (5) | C46—H46B | 0.9600 |
C21—H21 | 0.9300 | C46—H46C | 0.9600 |
C22—C23 | 1.343 (5) | N1—H1B | 0.821 (17) |
C22—H22 | 0.9300 | N1—H1A | 0.895 (16) |
C23—C24 | 1.382 (5) | O1—S1 | 1.4513 (18) |
C23—H23 | 0.9300 | O2—S1 | 1.4522 (19) |
C24—H24 | 0.9300 | O3—S1 | 1.458 (2) |
C25—C26 | 1.384 (4) | ||
N1—Ag1—P2 | 121.82 (6) | C29—C28—H28 | 120.2 |
N1—Ag1—P1 | 112.50 (6) | C28—C29—C30 | 120.1 (3) |
P2—Ag1—P1 | 122.09 (3) | C28—C29—H29 | 120.0 |
C2—C1—C6 | 118.5 (2) | C30—C29—H29 | 120.0 |
C2—C1—P2 | 119.46 (19) | C25—C30—C29 | 120.9 (3) |
C6—C1—P2 | 122.0 (2) | C25—C30—H30 | 119.6 |
C1—C2—C3 | 120.9 (3) | C29—C30—H30 | 119.6 |
C1—C2—H2 | 119.5 | C32—C31—C36 | 118.6 (3) |
C3—C2—H2 | 119.5 | C32—C31—P1 | 123.6 (2) |
C4—C3—C2 | 119.6 (3) | C36—C31—P1 | 117.8 (2) |
C4—C3—H3 | 120.2 | C31—C32—C33 | 119.6 (3) |
C2—C3—H3 | 120.2 | C31—C32—H32 | 120.2 |
C3—C4—C5 | 120.7 (3) | C33—C32—H32 | 120.2 |
C3—C4—H4 | 119.7 | C34—C33—C32 | 120.7 (3) |
C5—C4—H4 | 119.7 | C34—C33—H33 | 119.6 |
C4—C5—C6 | 119.9 (3) | C32—C33—H33 | 119.6 |
C4—C5—H5 | 120.1 | C33—C34—C35 | 120.2 (3) |
C6—C5—H5 | 120.1 | C33—C34—H34 | 119.9 |
C5—C6—C1 | 120.3 (3) | C35—C34—H34 | 119.9 |
C5—C6—H6 | 119.8 | C36—C35—C34 | 119.6 (4) |
C1—C6—H6 | 119.8 | C36—C35—H35 | 120.2 |
C12—C7—C8 | 119.1 (2) | C34—C35—H35 | 120.2 |
C12—C7—P2 | 124.2 (2) | C35—C36—C31 | 121.3 (3) |
C8—C7—P2 | 116.68 (19) | C35—C36—H36 | 119.4 |
C9—C8—C7 | 120.0 (3) | C31—C36—H36 | 119.4 |
C9—C8—H8 | 120.0 | C38—C37—C42 | 120.1 (2) |
C7—C8—H8 | 120.0 | C38—C37—S1 | 119.73 (19) |
C8—C9—C10 | 120.4 (3) | C42—C37—S1 | 120.12 (18) |
C8—C9—H9 | 119.8 | C39—C38—C37 | 121.6 (2) |
C10—C9—H9 | 119.8 | C39—C38—H38 | 119.2 |
C11—C10—C9 | 120.2 (3) | C37—C38—H38 | 119.2 |
C11—C10—H10 | 119.9 | C38—C39—C40 | 117.5 (3) |
C9—C10—H10 | 119.9 | C38—C39—C43 | 121.7 (3) |
C10—C11—C12 | 120.4 (3) | C40—C39—C43 | 120.8 (3) |
C10—C11—H11 | 119.8 | C41—C40—C39 | 123.2 (3) |
C12—C11—H11 | 119.8 | C41—C40—H40 | 118.4 |
C7—C12—C11 | 119.9 (3) | C39—C40—H40 | 118.4 |
C7—C12—H12 | 120.0 | C40—C41—C42 | 118.8 (2) |
C11—C12—H12 | 120.0 | C40—C41—C44 | 120.6 (2) |
C14—C13—C18 | 118.1 (3) | C42—C41—C44 | 120.6 (2) |
C14—C13—P2 | 124.6 (2) | C37—C42—C41 | 118.8 (2) |
C18—C13—P2 | 117.3 (2) | C37—C42—N1 | 121.2 (2) |
C13—C14—C15 | 120.4 (3) | C41—C42—N1 | 120.0 (2) |
C13—C14—H14 | 119.8 | C39—C43—H43A | 109.5 |
C15—C14—H14 | 119.8 | C39—C43—H43B | 109.5 |
C16—C15—C14 | 120.5 (3) | H43A—C43—H43B | 109.5 |
C16—C15—H15 | 119.7 | C39—C43—H43C | 109.5 |
C14—C15—H15 | 119.7 | H43A—C43—H43C | 109.5 |
C15—C16—C17 | 120.0 (3) | H43B—C43—H43C | 109.5 |
C15—C16—H16 | 120.0 | C41—C44—H44A | 109.5 |
C17—C16—H16 | 120.0 | C41—C44—H44B | 109.5 |
C16—C17—C18 | 120.3 (3) | H44A—C44—H44B | 109.5 |
C16—C17—H17 | 119.9 | C41—C44—H44C | 109.5 |
C18—C17—H17 | 119.9 | H44A—C44—H44C | 109.5 |
C13—C18—C17 | 120.7 (3) | H44B—C44—H44C | 109.5 |
C13—C18—H18 | 119.7 | N2—C45—C46 | 178.5 (10) |
C17—C18—H18 | 119.7 | C45—C46—H46A | 109.5 |
C20—C19—C24 | 116.9 (3) | C45—C46—H46B | 109.5 |
C20—C19—P1 | 118.4 (2) | H46A—C46—H46B | 109.5 |
C24—C19—P1 | 124.7 (2) | C45—C46—H46C | 109.5 |
C19—C20—C21 | 122.1 (3) | H46A—C46—H46C | 109.5 |
C19—C20—H20 | 118.9 | H46B—C46—H46C | 109.5 |
C21—C20—H20 | 118.9 | C42—N1—Ag1 | 114.06 (14) |
C22—C21—C20 | 120.0 (3) | C42—N1—H1B | 113 (2) |
C22—C21—H21 | 120.0 | Ag1—N1—H1B | 107 (2) |
C20—C21—H21 | 120.0 | C42—N1—H1A | 103.8 (16) |
C23—C22—C21 | 119.0 (3) | Ag1—N1—H1A | 95.6 (18) |
C23—C22—H22 | 120.5 | H1B—N1—H1A | 123 (2) |
C21—C22—H22 | 120.5 | O1—S1—O2 | 113.17 (12) |
C22—C23—C24 | 120.9 (3) | O1—S1—O3 | 112.21 (12) |
C22—C23—H23 | 119.6 | O2—S1—O3 | 113.08 (13) |
C24—C23—H23 | 119.6 | O1—S1—C37 | 105.25 (11) |
C19—C24—C23 | 121.1 (3) | O2—S1—C37 | 106.19 (12) |
C19—C24—H24 | 119.5 | O3—S1—C37 | 106.16 (11) |
C23—C24—H24 | 119.5 | C19—P1—C25 | 105.11 (12) |
C26—C25—C30 | 118.4 (3) | C19—P1—C31 | 102.19 (12) |
C26—C25—P1 | 117.3 (2) | C25—P1—C31 | 106.17 (12) |
C30—C25—P1 | 123.9 (2) | C19—P1—Ag1 | 111.92 (9) |
C25—C26—C27 | 120.7 (3) | C25—P1—Ag1 | 105.71 (8) |
C25—C26—H26 | 119.7 | C31—P1—Ag1 | 124.26 (9) |
C27—C26—H26 | 119.7 | C7—P2—C1 | 101.65 (11) |
C28—C27—C26 | 120.3 (3) | C7—P2—C13 | 103.80 (11) |
C28—C27—H27 | 119.9 | C1—P2—C13 | 105.01 (11) |
C26—C27—H27 | 119.9 | C7—P2—Ag1 | 115.28 (8) |
C27—C28—C29 | 119.6 (3) | C1—P2—Ag1 | 115.90 (8) |
C27—C28—H28 | 120.2 | C13—P2—Ag1 | 113.67 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1i | 0.90 (2) | 2.23 (2) | 3.026 (3) | 148 (2) |
N1—H1B···O3 | 0.82 (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 |
Mr | 873.69 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 13.782 (3), 12.252 (3), 25.243 (5) |
β (°) | 94.32 (3) |
V (Å3) | 4250.5 (15) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.64 |
Crystal size (mm) | 0.26 × 0.21 × 0.18 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.841, 0.892 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 39847, 9612, 7595 |
Rint | 0.047 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.092, 0.84 |
No. of reflections | 9612 |
No. of parameters | 506 |
No. of restraints | 3 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.45, −0.45 |
Computer programs: PROCESS-AUTO (Rigaku, 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Sheldrick, 1990).
Ag1—N1 | 2.393 (2) | Ag1—P1 | 2.5005 (8) |
Ag1—P2 | 2.4955 (9) | ||
N1—Ag1—P2 | 121.82 (6) | P2—Ag1—P1 | 122.09 (3) |
N1—Ag1—P1 | 112.50 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1i | 0.895 (16) | 2.23 (2) | 3.026 (3) | 147.8 (18) |
N1—H1B···O3 | 0.821 (17) | 2.21 (2) | 2.887 (3) | 139 (2) |
Symmetry code: (i) −x+3/2, y+1/2, −z+1/2. |
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).