Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807053524/cf2160sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807053524/cf2160Isup2.hkl |
CCDC reference: 672579
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.004 Å
- R factor = 0.034
- wR factor = 0.094
- Data-to-parameter ratio = 18.4
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X) Ag1 - P1 .. 10.15 su
Alert level C PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Ag1 - P2 .. 8.22 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for S1 PLAT245_ALERT_2_C U(iso) H1A Smaller than U(eq) O1W by ... 0.01 AngSq PLAT245_ALERT_2_C U(iso) H1B Smaller than U(eq) O1W by ... 0.01 AngSq
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 4
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
An aqueous solution (10 ml) of 2-amino-4,5-dimethylbenzenesulfonic acid (0.1005 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; triphenylphosphine (0.113 g, 0.5 mmol) in acetonitrile (10 ml) was then added and a white precipitate formed. The precipitate was dissolved by dropwise addition of an aqueous solution of NH3 (14 M). Colourless blocks of (I) were obtained by evaporation of the solution over several days at room temperature.
All H atoms on C atoms were positioned geometrically and refined as riding, with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C). The water H atoms were located in a difference Fourier map, and were refined with distance restraints of O—H = 0.85 (1) Å. The amino H atoms were located in a difference Fourier map and refined with Uiso(H) = 1.2Ueq(N).
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).
[Ag(C8H10NO3S)(C18H15P)2(H2O)] | F(000) = 1752 |
Mr = 850.66 | Dx = 1.415 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 9041 reflections |
a = 24.872 (5) Å | θ = 3.2–27.4° |
b = 14.634 (3) Å | µ = 0.68 mm−1 |
c = 11.010 (2) Å | T = 292 K |
β = 94.70 (3)° | Block, colourless |
V = 3994.0 (14) Å3 | 0.35 × 0.30 × 0.28 mm |
Z = 4 |
Rigaku R-AXIS RAPID CCD diffractometer | 9041 independent reflections |
Radiation source: fine-focus sealed tube | 6965 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.044 |
Detector resolution: 10.0 pixels mm-1 | θmax = 27.4°, θmin = 3.2° |
ω scans | h = −32→31 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −18→18 |
Tmin = 0.785, Tmax = 0.836 | l = −13→14 |
37956 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) = 0.094 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0476P)2 + 0.5293P] where P = (Fo2 + 2Fc2)/3 |
9041 reflections | (Δ/σ)max = 0.001 |
492 parameters | Δρmax = 0.30 e Å−3 |
4 restraints | Δρmin = −0.59 e Å−3 |
[Ag(C8H10NO3S)(C18H15P)2(H2O)] | V = 3994.0 (14) Å3 |
Mr = 850.66 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 24.872 (5) Å | µ = 0.68 mm−1 |
b = 14.634 (3) Å | T = 292 K |
c = 11.010 (2) Å | 0.35 × 0.30 × 0.28 mm |
β = 94.70 (3)° |
Rigaku R-AXIS RAPID CCD diffractometer | 9041 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 6965 reflections with I > 2σ(I) |
Tmin = 0.785, Tmax = 0.836 | Rint = 0.044 |
37956 measured reflections |
R[F2 > 2σ(F2)] = 0.035 | 4 restraints |
wR(F2) = 0.094 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | Δρmax = 0.30 e Å−3 |
9041 reflections | Δρmin = −0.59 e Å−3 |
492 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 | 0.737422 (7) | 0.536786 (13) | 0.982619 (17) | 0.03753 (7) | |
C1 | 0.85593 (9) | 0.41493 (17) | 1.1156 (2) | 0.0369 (5) | |
C2 | 0.90991 (10) | 0.3921 (2) | 1.1126 (2) | 0.0555 (8) | |
H2 | 0.9238 | 0.3801 | 1.0383 | 0.067* | |
C3 | 0.94317 (13) | 0.3872 (3) | 1.2191 (3) | 0.0734 (10) | |
H3 | 0.9793 | 0.3714 | 1.2167 | 0.088* | |
C4 | 0.92291 (13) | 0.4054 (3) | 1.3277 (3) | 0.0674 (9) | |
H4 | 0.9455 | 0.4018 | 1.3992 | 0.081* | |
C5 | 0.87000 (13) | 0.4288 (2) | 1.3333 (3) | 0.0567 (8) | |
H5 | 0.8565 | 0.4409 | 1.4080 | 0.068* | |
C6 | 0.83653 (11) | 0.43426 (19) | 1.2262 (2) | 0.0432 (6) | |
H6 | 0.8006 | 0.4512 | 1.2293 | 0.052* | |
C7 | 0.78305 (9) | 0.30617 (17) | 0.9581 (2) | 0.0376 (5) | |
C8 | 0.79251 (12) | 0.2379 (2) | 1.0447 (3) | 0.0504 (7) | |
H8 | 0.8149 | 0.2499 | 1.1148 | 0.061* | |
C9 | 0.76929 (13) | 0.1524 (2) | 1.0287 (3) | 0.0643 (9) | |
H9 | 0.7757 | 0.1077 | 1.0881 | 0.077* | |
C10 | 0.73683 (12) | 0.1338 (2) | 0.9248 (3) | 0.0621 (8) | |
H10 | 0.7213 | 0.0763 | 0.9134 | 0.074* | |
C11 | 0.72722 (12) | 0.2005 (2) | 0.8372 (3) | 0.0630 (9) | |
H11 | 0.7057 | 0.1875 | 0.7662 | 0.076* | |
C12 | 0.74945 (10) | 0.2866 (2) | 0.8547 (3) | 0.0494 (7) | |
H12 | 0.7418 | 0.3318 | 0.7966 | 0.059* | |
C13 | 0.85297 (9) | 0.43810 (19) | 0.8548 (2) | 0.0379 (6) | |
C14 | 0.87784 (10) | 0.3656 (2) | 0.7996 (2) | 0.0489 (7) | |
H14 | 0.8717 | 0.3058 | 0.8235 | 0.059* | |
C15 | 0.91199 (12) | 0.3835 (3) | 0.7084 (3) | 0.0665 (9) | |
H15 | 0.9286 | 0.3353 | 0.6711 | 0.080* | |
C16 | 0.92135 (14) | 0.4717 (3) | 0.6729 (3) | 0.0714 (11) | |
H16 | 0.9442 | 0.4827 | 0.6117 | 0.086* | |
C17 | 0.89712 (14) | 0.5441 (3) | 0.7275 (3) | 0.0691 (10) | |
H17 | 0.9037 | 0.6037 | 0.7036 | 0.083* | |
C18 | 0.86258 (12) | 0.5271 (2) | 0.8190 (3) | 0.0518 (7) | |
H18 | 0.8460 | 0.5756 | 0.8558 | 0.062* | |
C19 | 0.61800 (9) | 0.42070 (18) | 1.0728 (2) | 0.0386 (5) | |
C20 | 0.63163 (12) | 0.3347 (2) | 1.0330 (3) | 0.0531 (7) | |
H20 | 0.6499 | 0.3288 | 0.9630 | 0.064* | |
C21 | 0.61829 (15) | 0.2575 (2) | 1.0960 (4) | 0.0718 (10) | |
H21 | 0.6271 | 0.2000 | 1.0678 | 0.086* | |
C22 | 0.59193 (14) | 0.2658 (3) | 1.2007 (3) | 0.0731 (10) | |
H22 | 0.5832 | 0.2139 | 1.2437 | 0.088* | |
C23 | 0.57876 (13) | 0.3495 (3) | 1.2410 (3) | 0.0699 (10) | |
H23 | 0.5609 | 0.3546 | 1.3116 | 0.084* | |
C24 | 0.59156 (11) | 0.4279 (2) | 1.1782 (3) | 0.0536 (7) | |
H24 | 0.5824 | 0.4851 | 1.2069 | 0.064* | |
C25 | 0.60430 (9) | 0.49905 (18) | 0.8353 (2) | 0.0376 (5) | |
C26 | 0.63227 (12) | 0.5162 (2) | 0.7327 (3) | 0.0518 (7) | |
H26 | 0.6674 | 0.5385 | 0.7426 | 0.062* | |
C27 | 0.60844 (15) | 0.5006 (3) | 0.6170 (3) | 0.0666 (9) | |
H27 | 0.6276 | 0.5124 | 0.5496 | 0.080* | |
C28 | 0.55659 (14) | 0.4678 (2) | 0.6009 (3) | 0.0663 (9) | |
H28 | 0.5406 | 0.4570 | 0.5228 | 0.080* | |
C29 | 0.52824 (12) | 0.4509 (2) | 0.7018 (3) | 0.0605 (9) | |
H29 | 0.4930 | 0.4292 | 0.6912 | 0.073* | |
C30 | 0.55190 (11) | 0.46624 (19) | 0.8185 (3) | 0.0491 (7) | |
H30 | 0.5326 | 0.4545 | 0.8856 | 0.059* | |
C31 | 0.60500 (9) | 0.61544 (17) | 1.0500 (2) | 0.0348 (5) | |
C32 | 0.55896 (10) | 0.65660 (19) | 0.9950 (3) | 0.0466 (6) | |
H32 | 0.5433 | 0.6341 | 0.9214 | 0.056* | |
C33 | 0.53621 (12) | 0.7313 (2) | 1.0495 (3) | 0.0606 (8) | |
H33 | 0.5056 | 0.7589 | 1.0118 | 0.073* | |
C34 | 0.55873 (12) | 0.7648 (2) | 1.1591 (3) | 0.0659 (9) | |
H34 | 0.5432 | 0.8146 | 1.1953 | 0.079* | |
C35 | 0.60383 (12) | 0.7248 (2) | 1.2143 (3) | 0.0591 (8) | |
H35 | 0.6189 | 0.7475 | 1.2882 | 0.071* | |
C36 | 0.62738 (10) | 0.6505 (2) | 1.1611 (2) | 0.0448 (6) | |
H36 | 0.6582 | 0.6238 | 1.1995 | 0.054* | |
C37 | 0.80874 (10) | 0.79236 (17) | 0.9918 (2) | 0.0370 (5) | |
C38 | 0.85665 (11) | 0.82206 (19) | 0.9475 (2) | 0.0459 (6) | |
H38 | 0.8557 | 0.8732 | 0.8972 | 0.055* | |
C39 | 0.90552 (11) | 0.7785 (2) | 0.9752 (3) | 0.0511 (7) | |
C40 | 0.90660 (10) | 0.7015 (2) | 1.0502 (3) | 0.0494 (7) | |
C41 | 0.85908 (10) | 0.67250 (19) | 1.0955 (2) | 0.0434 (6) | |
H41 | 0.8603 | 0.6226 | 1.1480 | 0.052* | |
C42 | 0.80932 (10) | 0.71503 (17) | 1.0657 (2) | 0.0350 (5) | |
C43 | 0.95591 (13) | 0.8125 (3) | 0.9209 (4) | 0.0835 (12) | |
H43A | 0.9864 | 0.8053 | 0.9793 | 0.125* | |
H43B | 0.9516 | 0.8759 | 0.8997 | 0.125* | |
H43C | 0.9616 | 0.7777 | 0.8491 | 0.125* | |
C44 | 0.95793 (12) | 0.6482 (3) | 1.0810 (3) | 0.0760 (10) | |
H44A | 0.9851 | 0.6882 | 1.1182 | 0.114* | |
H44B | 0.9702 | 0.6228 | 1.0079 | 0.114* | |
H44C | 0.9511 | 0.5998 | 1.1366 | 0.114* | |
N1 | 0.76224 (8) | 0.67411 (15) | 1.1049 (2) | 0.0376 (5) | |
O1 | 0.75906 (9) | 0.91154 (14) | 0.84892 (17) | 0.0573 (5) | |
O2 | 0.73943 (10) | 0.91015 (17) | 1.05962 (18) | 0.0751 (7) | |
O3 | 0.70682 (8) | 0.78944 (15) | 0.9241 (2) | 0.0741 (7) | |
O1W | 0.74902 (10) | 0.63686 (16) | 0.80672 (19) | 0.0616 (6) | |
S1 | 0.74872 (3) | 0.85648 (5) | 0.95299 (6) | 0.04396 (16) | |
P1 | 0.63905 (2) | 0.51895 (4) | 0.98561 (6) | 0.03284 (14) | |
P2 | 0.80913 (2) | 0.42236 (4) | 0.97888 (6) | 0.03333 (14) | |
H1A | 0.7255 (11) | 0.683 (2) | 0.806 (3) | 0.050* | |
H1B | 0.7489 (11) | 0.624 (2) | 0.733 (2) | 0.050* | |
H1C | 0.7682 (10) | 0.6577 (19) | 1.185 (2) | 0.050* | |
H1D | 0.7351 (11) | 0.7059 (19) | 1.090 (3) | 0.050* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ag1 | 0.03204 (11) | 0.03472 (11) | 0.04610 (12) | 0.00212 (7) | 0.00494 (8) | −0.00024 (8) |
C1 | 0.0379 (13) | 0.0346 (14) | 0.0382 (13) | 0.0038 (10) | 0.0027 (10) | −0.0028 (11) |
C2 | 0.0441 (15) | 0.081 (2) | 0.0407 (15) | 0.0188 (14) | −0.0007 (12) | −0.0118 (15) |
C3 | 0.0502 (18) | 0.099 (3) | 0.068 (2) | 0.0217 (18) | −0.0113 (15) | −0.016 (2) |
C4 | 0.076 (2) | 0.079 (3) | 0.0433 (18) | 0.0106 (18) | −0.0200 (15) | −0.0060 (17) |
C5 | 0.072 (2) | 0.063 (2) | 0.0346 (15) | 0.0018 (16) | 0.0026 (13) | −0.0038 (14) |
C6 | 0.0489 (15) | 0.0417 (15) | 0.0397 (14) | 0.0025 (12) | 0.0073 (11) | −0.0018 (12) |
C7 | 0.0335 (12) | 0.0373 (14) | 0.0429 (14) | 0.0049 (10) | 0.0083 (10) | −0.0022 (11) |
C8 | 0.0662 (18) | 0.0432 (17) | 0.0416 (15) | −0.0003 (13) | 0.0030 (13) | 0.0011 (13) |
C9 | 0.087 (2) | 0.0461 (19) | 0.061 (2) | −0.0015 (16) | 0.0143 (18) | 0.0021 (16) |
C10 | 0.0621 (19) | 0.0438 (18) | 0.083 (2) | −0.0082 (14) | 0.0197 (16) | −0.0161 (17) |
C11 | 0.0484 (17) | 0.060 (2) | 0.079 (2) | −0.0008 (14) | −0.0019 (15) | −0.0253 (18) |
C12 | 0.0457 (15) | 0.0504 (18) | 0.0511 (17) | 0.0022 (12) | −0.0033 (12) | −0.0030 (14) |
C13 | 0.0360 (12) | 0.0507 (16) | 0.0271 (12) | 0.0019 (11) | 0.0029 (9) | −0.0043 (11) |
C14 | 0.0441 (14) | 0.0575 (19) | 0.0460 (15) | 0.0052 (13) | 0.0080 (12) | −0.0099 (14) |
C15 | 0.0505 (17) | 0.089 (3) | 0.063 (2) | −0.0007 (17) | 0.0243 (15) | −0.0230 (19) |
C16 | 0.064 (2) | 0.110 (3) | 0.0437 (18) | −0.024 (2) | 0.0216 (15) | −0.0125 (19) |
C17 | 0.072 (2) | 0.078 (3) | 0.060 (2) | −0.0199 (18) | 0.0207 (17) | 0.0101 (18) |
C18 | 0.0610 (18) | 0.0531 (19) | 0.0427 (16) | −0.0041 (13) | 0.0132 (13) | 0.0032 (13) |
C19 | 0.0343 (12) | 0.0359 (14) | 0.0456 (14) | −0.0023 (10) | 0.0025 (10) | 0.0039 (11) |
C20 | 0.0633 (18) | 0.0420 (17) | 0.0540 (17) | −0.0009 (13) | 0.0039 (14) | 0.0010 (14) |
C21 | 0.088 (2) | 0.0345 (17) | 0.092 (3) | −0.0097 (16) | −0.003 (2) | 0.0081 (17) |
C22 | 0.080 (2) | 0.064 (2) | 0.073 (2) | −0.0299 (19) | −0.0077 (18) | 0.030 (2) |
C23 | 0.071 (2) | 0.077 (3) | 0.064 (2) | −0.0171 (18) | 0.0204 (16) | 0.0200 (19) |
C24 | 0.0536 (17) | 0.0521 (18) | 0.0572 (18) | −0.0026 (14) | 0.0177 (14) | 0.0082 (14) |
C25 | 0.0378 (13) | 0.0348 (13) | 0.0396 (14) | 0.0040 (10) | −0.0006 (10) | −0.0052 (11) |
C26 | 0.0555 (17) | 0.0542 (19) | 0.0459 (17) | −0.0013 (14) | 0.0054 (13) | −0.0024 (14) |
C27 | 0.086 (2) | 0.073 (2) | 0.0409 (18) | 0.0117 (19) | 0.0054 (16) | −0.0024 (16) |
C28 | 0.073 (2) | 0.068 (2) | 0.055 (2) | 0.0264 (17) | −0.0168 (16) | −0.0166 (17) |
C29 | 0.0470 (16) | 0.059 (2) | 0.072 (2) | 0.0107 (13) | −0.0181 (15) | −0.0200 (17) |
C30 | 0.0404 (14) | 0.0484 (17) | 0.0579 (18) | 0.0030 (12) | 0.0008 (12) | −0.0076 (14) |
C31 | 0.0322 (12) | 0.0338 (13) | 0.0388 (13) | −0.0014 (9) | 0.0059 (10) | −0.0009 (10) |
C32 | 0.0438 (14) | 0.0456 (16) | 0.0498 (16) | 0.0063 (12) | 0.0004 (11) | −0.0014 (13) |
C33 | 0.0543 (17) | 0.055 (2) | 0.071 (2) | 0.0203 (14) | −0.0015 (15) | −0.0078 (16) |
C34 | 0.0576 (18) | 0.054 (2) | 0.087 (2) | 0.0116 (15) | 0.0106 (17) | −0.0243 (18) |
C35 | 0.0485 (16) | 0.061 (2) | 0.067 (2) | −0.0026 (14) | 0.0052 (14) | −0.0297 (17) |
C36 | 0.0359 (13) | 0.0506 (17) | 0.0475 (15) | 0.0019 (11) | 0.0018 (11) | −0.0094 (13) |
C37 | 0.0465 (14) | 0.0320 (14) | 0.0329 (13) | −0.0073 (10) | 0.0058 (10) | −0.0023 (10) |
C38 | 0.0552 (16) | 0.0417 (16) | 0.0421 (15) | −0.0142 (12) | 0.0119 (12) | −0.0016 (12) |
C39 | 0.0449 (15) | 0.062 (2) | 0.0474 (16) | −0.0157 (13) | 0.0090 (12) | −0.0057 (14) |
C40 | 0.0406 (14) | 0.062 (2) | 0.0458 (16) | −0.0024 (12) | 0.0022 (11) | −0.0077 (14) |
C41 | 0.0492 (15) | 0.0409 (15) | 0.0401 (14) | 0.0001 (12) | 0.0033 (11) | 0.0011 (12) |
C42 | 0.0429 (13) | 0.0342 (13) | 0.0283 (12) | −0.0069 (10) | 0.0053 (9) | −0.0045 (10) |
C43 | 0.059 (2) | 0.108 (3) | 0.086 (3) | −0.024 (2) | 0.0226 (18) | 0.007 (2) |
C44 | 0.0468 (17) | 0.104 (3) | 0.076 (2) | 0.0129 (18) | −0.0003 (15) | 0.004 (2) |
N1 | 0.0402 (11) | 0.0375 (12) | 0.0358 (11) | −0.0019 (9) | 0.0067 (9) | −0.0001 (9) |
O1 | 0.0845 (14) | 0.0471 (12) | 0.0418 (11) | 0.0087 (10) | 0.0135 (10) | 0.0097 (9) |
O2 | 0.1054 (18) | 0.0802 (18) | 0.0420 (12) | 0.0395 (14) | 0.0208 (12) | −0.0009 (11) |
O3 | 0.0522 (12) | 0.0569 (15) | 0.1095 (19) | −0.0024 (10) | −0.0162 (12) | 0.0196 (14) |
O1W | 0.0907 (16) | 0.0542 (14) | 0.0399 (11) | −0.0020 (11) | 0.0049 (11) | 0.0082 (11) |
S1 | 0.0561 (4) | 0.0383 (4) | 0.0383 (3) | 0.0045 (3) | 0.0090 (3) | 0.0036 (3) |
P1 | 0.0293 (3) | 0.0332 (3) | 0.0363 (3) | 0.0005 (2) | 0.0042 (2) | 0.0002 (3) |
P2 | 0.0323 (3) | 0.0352 (3) | 0.0329 (3) | 0.0048 (2) | 0.0053 (2) | −0.0005 (3) |
Ag1—P2 | 2.4492 (7) | C24—H24 | 0.930 |
Ag1—P1 | 2.4637 (8) | C25—C30 | 1.387 (4) |
Ag1—O1W | 2.464 (2) | C25—C26 | 1.397 (4) |
Ag1—N1 | 2.469 (2) | C25—P1 | 1.827 (3) |
C1—C6 | 1.376 (3) | C26—C27 | 1.379 (4) |
C1—C2 | 1.387 (3) | C26—H26 | 0.930 |
C1—P2 | 1.829 (3) | C27—C28 | 1.374 (5) |
C2—C3 | 1.381 (4) | C27—H27 | 0.930 |
C2—H2 | 0.930 | C28—C29 | 1.387 (5) |
C3—C4 | 1.361 (4) | C28—H28 | 0.930 |
C3—H3 | 0.930 | C29—C30 | 1.386 (4) |
C4—C5 | 1.366 (4) | C29—H29 | 0.930 |
C4—H4 | 0.930 | C30—H30 | 0.930 |
C5—C6 | 1.389 (4) | C31—C32 | 1.388 (3) |
C5—H5 | 0.930 | C31—C36 | 1.399 (3) |
C6—H6 | 0.930 | C31—P1 | 1.820 (2) |
C7—C12 | 1.386 (4) | C32—C33 | 1.390 (4) |
C7—C8 | 1.387 (4) | C32—H32 | 0.930 |
C7—P2 | 1.828 (3) | C33—C34 | 1.378 (4) |
C8—C9 | 1.383 (4) | C33—H33 | 0.930 |
C8—H8 | 0.930 | C34—C35 | 1.363 (4) |
C9—C10 | 1.373 (4) | C34—H34 | 0.930 |
C9—H9 | 0.930 | C35—C36 | 1.387 (4) |
C10—C11 | 1.379 (5) | C35—H35 | 0.930 |
C10—H10 | 0.930 | C36—H36 | 0.930 |
C11—C12 | 1.383 (4) | C37—C42 | 1.393 (3) |
C11—H11 | 0.930 | C37—C38 | 1.394 (3) |
C12—H12 | 0.930 | C37—S1 | 1.785 (3) |
C13—C18 | 1.387 (4) | C38—C39 | 1.384 (4) |
C13—C14 | 1.392 (4) | C38—H38 | 0.930 |
C13—P2 | 1.831 (2) | C39—C40 | 1.397 (4) |
C14—C15 | 1.393 (4) | C39—C43 | 1.516 (4) |
C14—H14 | 0.930 | C40—C41 | 1.386 (4) |
C15—C16 | 1.374 (5) | C40—C44 | 1.511 (4) |
C15—H15 | 0.930 | C41—C42 | 1.400 (3) |
C16—C17 | 1.381 (5) | C41—H41 | 0.930 |
C16—H16 | 0.930 | C42—N1 | 1.414 (3) |
C17—C18 | 1.399 (4) | C43—H43A | 0.960 |
C17—H17 | 0.930 | C43—H43B | 0.960 |
C18—H18 | 0.930 | C43—H43C | 0.960 |
C19—C24 | 1.383 (4) | C44—H44A | 0.960 |
C19—C20 | 1.385 (4) | C44—H44B | 0.960 |
C19—P1 | 1.829 (3) | C44—H44C | 0.960 |
C20—C21 | 1.380 (4) | N1—H1C | 0.92 (3) |
C20—H20 | 0.930 | N1—H1D | 0.83 (3) |
C21—C22 | 1.377 (5) | O1—S1 | 1.4411 (19) |
C21—H21 | 0.930 | O2—S1 | 1.447 (2) |
C22—C23 | 1.351 (5) | O3—S1 | 1.448 (2) |
C22—H22 | 0.930 | O1W—H1A | 0.89 (3) |
C23—C24 | 1.391 (4) | O1W—H1B | 0.83 (3) |
C23—H23 | 0.930 | ||
P2—Ag1—P1 | 130.79 (2) | C26—C27—H27 | 119.8 |
P2—Ag1—O1W | 105.12 (6) | C27—C28—C29 | 119.5 (3) |
P1—Ag1—O1W | 104.71 (6) | C27—C28—H28 | 120.3 |
P2—Ag1—N1 | 114.57 (6) | C29—C28—H28 | 120.3 |
P1—Ag1—N1 | 106.45 (5) | C28—C29—C30 | 120.6 (3) |
O1W—Ag1—N1 | 84.53 (8) | C28—C29—H29 | 119.7 |
C6—C1—C2 | 118.8 (2) | C30—C29—H29 | 119.7 |
C6—C1—P2 | 118.07 (19) | C29—C30—C25 | 120.1 (3) |
C2—C1—P2 | 123.16 (19) | C29—C30—H30 | 119.9 |
C3—C2—C1 | 120.4 (3) | C25—C30—H30 | 119.9 |
C3—C2—H2 | 119.8 | C32—C31—C36 | 118.5 (2) |
C1—C2—H2 | 119.8 | C32—C31—P1 | 124.05 (19) |
C4—C3—C2 | 119.8 (3) | C36—C31—P1 | 117.43 (18) |
C4—C3—H3 | 120.1 | C31—C32—C33 | 120.2 (3) |
C2—C3—H3 | 120.1 | C31—C32—H32 | 119.9 |
C3—C4—C5 | 121.1 (3) | C33—C32—H32 | 119.9 |
C3—C4—H4 | 119.5 | C34—C33—C32 | 120.5 (3) |
C5—C4—H4 | 119.5 | C34—C33—H33 | 119.8 |
C4—C5—C6 | 119.2 (3) | C32—C33—H33 | 119.8 |
C4—C5—H5 | 120.4 | C35—C34—C33 | 119.9 (3) |
C6—C5—H5 | 120.4 | C35—C34—H34 | 120.1 |
C1—C6—C5 | 120.7 (3) | C33—C34—H34 | 120.1 |
C1—C6—H6 | 119.7 | C34—C35—C36 | 120.6 (3) |
C5—C6—H6 | 119.7 | C34—C35—H35 | 119.7 |
C12—C7—C8 | 118.2 (3) | C36—C35—H35 | 119.7 |
C12—C7—P2 | 118.6 (2) | C35—C36—C31 | 120.3 (3) |
C8—C7—P2 | 123.0 (2) | C35—C36—H36 | 119.8 |
C9—C8—C7 | 121.2 (3) | C31—C36—H36 | 119.8 |
C9—C8—H8 | 119.4 | C42—C37—C38 | 119.3 (2) |
C7—C8—H8 | 119.4 | C42—C37—S1 | 122.34 (18) |
C10—C9—C8 | 119.8 (3) | C38—C37—S1 | 118.3 (2) |
C10—C9—H9 | 120.1 | C39—C38—C37 | 122.7 (3) |
C8—C9—H9 | 120.1 | C39—C38—H38 | 118.7 |
C9—C10—C11 | 119.9 (3) | C37—C38—H38 | 118.7 |
C9—C10—H10 | 120.1 | C38—C39—C40 | 118.4 (2) |
C11—C10—H10 | 120.1 | C38—C39—C43 | 120.1 (3) |
C10—C11—C12 | 120.2 (3) | C40—C39—C43 | 121.4 (3) |
C10—C11—H11 | 119.9 | C41—C40—C39 | 119.0 (3) |
C12—C11—H11 | 119.9 | C41—C40—C44 | 119.4 (3) |
C11—C12—C7 | 120.7 (3) | C39—C40—C44 | 121.6 (3) |
C11—C12—H12 | 119.7 | C40—C41—C42 | 122.9 (3) |
C7—C12—H12 | 119.7 | C40—C41—H41 | 118.6 |
C18—C13—C14 | 119.9 (2) | C42—C41—H41 | 118.6 |
C18—C13—P2 | 117.2 (2) | C37—C42—C41 | 117.7 (2) |
C14—C13—P2 | 122.9 (2) | C37—C42—N1 | 123.6 (2) |
C13—C14—C15 | 119.4 (3) | C41—C42—N1 | 118.6 (2) |
C13—C14—H14 | 120.3 | C39—C43—H43A | 109.5 |
C15—C14—H14 | 120.3 | C39—C43—H43B | 109.5 |
C16—C15—C14 | 120.6 (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 | 120.5 (3) | H43B—C43—H43C | 109.5 |
C15—C16—H16 | 119.8 | C40—C44—H44A | 109.5 |
C17—C16—H16 | 119.8 | C40—C44—H44B | 109.5 |
C16—C17—C18 | 119.5 (3) | H44A—C44—H44B | 109.5 |
C16—C17—H17 | 120.2 | C40—C44—H44C | 109.5 |
C18—C17—H17 | 120.2 | H44A—C44—H44C | 109.5 |
C13—C18—C17 | 120.1 (3) | H44B—C44—H44C | 109.5 |
C13—C18—H18 | 119.9 | C42—N1—Ag1 | 110.78 (15) |
C17—C18—H18 | 119.9 | C42—N1—H1C | 109.5 (17) |
C24—C19—C20 | 118.8 (3) | Ag1—N1—H1C | 109.1 (18) |
C24—C19—P1 | 123.8 (2) | C42—N1—H1D | 113 (2) |
C20—C19—P1 | 117.4 (2) | Ag1—N1—H1D | 101 (2) |
C21—C20—C19 | 120.6 (3) | H1C—N1—H1D | 113 (3) |
C21—C20—H20 | 119.7 | Ag1—O1W—H1A | 109.5 (19) |
C19—C20—H20 | 119.7 | Ag1—O1W—H1B | 130 (2) |
C22—C21—C20 | 120.0 (3) | H1A—O1W—H1B | 103 (3) |
C22—C21—H21 | 120.0 | O1—S1—O2 | 113.11 (14) |
C20—C21—H21 | 120.0 | O1—S1—O3 | 112.10 (14) |
C23—C22—C21 | 119.9 (3) | O2—S1—O3 | 112.74 (16) |
C23—C22—H22 | 120.0 | O1—S1—C37 | 106.49 (12) |
C21—C22—H22 | 120.0 | O2—S1—C37 | 106.09 (13) |
C22—C23—C24 | 120.9 (3) | O3—S1—C37 | 105.62 (12) |
C22—C23—H23 | 119.5 | C31—P1—C25 | 106.04 (11) |
C24—C23—H23 | 119.5 | C31—P1—C19 | 104.05 (12) |
C19—C24—C23 | 119.8 (3) | C25—P1—C19 | 102.48 (12) |
C19—C24—H24 | 120.1 | C31—P1—Ag1 | 114.67 (8) |
C23—C24—H24 | 120.1 | C25—P1—Ag1 | 113.66 (8) |
C30—C25—C26 | 118.7 (3) | C19—P1—Ag1 | 114.68 (8) |
C30—C25—P1 | 123.0 (2) | C7—P2—C1 | 104.07 (12) |
C26—C25—P1 | 118.3 (2) | C7—P2—C13 | 104.51 (11) |
C27—C26—C25 | 120.8 (3) | C1—P2—C13 | 104.10 (11) |
C27—C26—H26 | 119.6 | C7—P2—Ag1 | 112.75 (8) |
C25—C26—H26 | 119.6 | C1—P2—Ag1 | 116.24 (8) |
C28—C27—C26 | 120.3 (3) | C13—P2—Ag1 | 113.93 (9) |
C28—C27—H27 | 119.8 | ||
C6—C1—C2—C3 | 1.3 (5) | C41—C42—N1—Ag1 | −73.9 (2) |
P2—C1—C2—C3 | −179.6 (3) | P2—Ag1—N1—C42 | 55.17 (18) |
C1—C2—C3—C4 | −0.4 (6) | P1—Ag1—N1—C42 | −152.72 (15) |
C2—C3—C4—C5 | −0.1 (6) | O1W—Ag1—N1—C42 | −48.97 (17) |
C3—C4—C5—C6 | −0.2 (6) | C42—C37—S1—O1 | −162.6 (2) |
C2—C1—C6—C5 | −1.6 (4) | C38—C37—S1—O1 | 18.4 (2) |
P2—C1—C6—C5 | 179.3 (2) | C42—C37—S1—O2 | 76.7 (2) |
C4—C5—C6—C1 | 1.1 (5) | C38—C37—S1—O2 | −102.4 (2) |
C12—C7—C8—C9 | 0.2 (4) | C42—C37—S1—O3 | −43.2 (2) |
P2—C7—C8—C9 | 176.0 (2) | C38—C37—S1—O3 | 137.7 (2) |
C7—C8—C9—C10 | 0.9 (5) | C32—C31—P1—C25 | 5.3 (3) |
C8—C9—C10—C11 | −0.4 (5) | C36—C31—P1—C25 | −173.9 (2) |
C9—C10—C11—C12 | −1.1 (5) | C32—C31—P1—C19 | −102.4 (2) |
C10—C11—C12—C7 | 2.2 (4) | C36—C31—P1—C19 | 78.4 (2) |
C8—C7—C12—C11 | −1.8 (4) | C32—C31—P1—Ag1 | 131.5 (2) |
P2—C7—C12—C11 | −177.7 (2) | C36—C31—P1—Ag1 | −47.6 (2) |
C18—C13—C14—C15 | −0.3 (4) | C30—C25—P1—C31 | −68.7 (3) |
P2—C13—C14—C15 | −178.0 (2) | C26—C25—P1—C31 | 112.4 (2) |
C13—C14—C15—C16 | 0.2 (5) | C30—C25—P1—C19 | 40.1 (3) |
C14—C15—C16—C17 | 0.2 (6) | C26—C25—P1—C19 | −138.8 (2) |
C15—C16—C17—C18 | −0.4 (6) | C30—C25—P1—Ag1 | 164.4 (2) |
C14—C13—C18—C17 | 0.1 (4) | C26—C25—P1—Ag1 | −14.4 (3) |
P2—C13—C18—C17 | 177.9 (2) | C24—C19—P1—C31 | −11.7 (3) |
C16—C17—C18—C13 | 0.3 (5) | C20—C19—P1—C31 | 171.2 (2) |
C24—C19—C20—C21 | 1.1 (4) | C24—C19—P1—C25 | −122.0 (2) |
P1—C19—C20—C21 | 178.4 (2) | C20—C19—P1—C25 | 60.9 (2) |
C19—C20—C21—C22 | −1.0 (5) | C24—C19—P1—Ag1 | 114.4 (2) |
C20—C21—C22—C23 | 0.6 (5) | C20—C19—P1—Ag1 | −62.8 (2) |
C21—C22—C23—C24 | −0.2 (5) | P2—Ag1—P1—C31 | 155.69 (9) |
C20—C19—C24—C23 | −0.6 (4) | O1W—Ag1—P1—C31 | −78.68 (11) |
P1—C19—C24—C23 | −177.7 (2) | N1—Ag1—P1—C31 | 9.87 (11) |
C22—C23—C24—C19 | 0.2 (5) | P2—Ag1—P1—C25 | −82.10 (10) |
C30—C25—C26—C27 | −0.3 (4) | O1W—Ag1—P1—C25 | 43.53 (11) |
P1—C25—C26—C27 | 178.6 (3) | N1—Ag1—P1—C25 | 132.09 (11) |
C25—C26—C27—C28 | 0.0 (5) | P2—Ag1—P1—C19 | 35.35 (10) |
C26—C27—C28—C29 | 0.4 (5) | O1W—Ag1—P1—C19 | 160.98 (11) |
C27—C28—C29—C30 | −0.5 (5) | N1—Ag1—P1—C19 | −110.47 (11) |
C28—C29—C30—C25 | 0.3 (4) | C12—C7—P2—C1 | −174.55 (19) |
C26—C25—C30—C29 | 0.1 (4) | C8—C7—P2—C1 | 9.7 (2) |
P1—C25—C30—C29 | −178.7 (2) | C12—C7—P2—C13 | −65.6 (2) |
C36—C31—C32—C33 | 0.5 (4) | C8—C7—P2—C13 | 118.6 (2) |
P1—C31—C32—C33 | −178.7 (2) | C12—C7—P2—Ag1 | 58.6 (2) |
C31—C32—C33—C34 | −0.6 (5) | C8—C7—P2—Ag1 | −117.1 (2) |
C32—C33—C34—C35 | 0.4 (5) | C6—C1—P2—C7 | −92.8 (2) |
C33—C34—C35—C36 | 0.0 (5) | C2—C1—P2—C7 | 88.2 (3) |
C34—C35—C36—C31 | −0.1 (5) | C6—C1—P2—C13 | 158.0 (2) |
C32—C31—C36—C35 | −0.1 (4) | C2—C1—P2—C13 | −21.0 (3) |
P1—C31—C36—C35 | 179.1 (2) | C6—C1—P2—Ag1 | 31.9 (2) |
C42—C37—C38—C39 | −0.9 (4) | C2—C1—P2—Ag1 | −147.2 (2) |
S1—C37—C38—C39 | 178.2 (2) | C18—C13—P2—C7 | 156.7 (2) |
C37—C38—C39—C40 | 0.3 (4) | C14—C13—P2—C7 | −25.5 (2) |
C37—C38—C39—C43 | 178.1 (3) | C18—C13—P2—C1 | −94.4 (2) |
C38—C39—C40—C41 | −1.0 (4) | C14—C13—P2—C1 | 83.4 (2) |
C43—C39—C40—C41 | −178.8 (3) | C18—C13—P2—Ag1 | 33.2 (2) |
C38—C39—C40—C44 | 177.8 (3) | C14—C13—P2—Ag1 | −149.02 (19) |
C43—C39—C40—C44 | 0.0 (5) | P1—Ag1—P2—C7 | 7.55 (10) |
C39—C40—C41—C42 | 2.5 (4) | O1W—Ag1—P2—C7 | −117.92 (11) |
C44—C40—C41—C42 | −176.3 (3) | N1—Ag1—P2—C7 | 151.22 (10) |
C38—C37—C42—C41 | 2.2 (3) | P1—Ag1—P2—C1 | −112.49 (9) |
S1—C37—C42—C41 | −176.85 (19) | O1W—Ag1—P2—C1 | 122.03 (11) |
C38—C37—C42—N1 | −173.3 (2) | N1—Ag1—P2—C1 | 31.18 (11) |
S1—C37—C42—N1 | 7.6 (3) | P1—Ag1—P2—C13 | 126.46 (9) |
C40—C41—C42—C37 | −3.1 (4) | O1W—Ag1—P2—C13 | 0.98 (11) |
C40—C41—C42—N1 | 172.7 (2) | N1—Ag1—P2—C13 | −89.88 (11) |
C37—C42—N1—Ag1 | 101.6 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1B···O2i | 0.83 (3) | 1.97 (3) | 2.797 (3) | 173 (3) |
O1W—H1A···O3 | 0.89 (3) | 2.10 (3) | 2.825 (4) | 137 (3) |
N1—H1C···O1ii | 0.92 (3) | 2.09 (3) | 2.972 (3) | 159 (2) |
N1—H1D···O3 | 0.83 (3) | 2.26 (3) | 2.875 (3) | 131 (3) |
Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x, −y+3/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [Ag(C8H10NO3S)(C18H15P)2(H2O)] |
Mr | 850.66 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 292 |
a, b, c (Å) | 24.872 (5), 14.634 (3), 11.010 (2) |
β (°) | 94.70 (3) |
V (Å3) | 3994.0 (14) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.68 |
Crystal size (mm) | 0.35 × 0.30 × 0.28 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID CCD diffractometer |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.785, 0.836 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 37956, 9041, 6965 |
Rint | 0.044 |
(sin θ/λ)max (Å−1) | 0.648 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.035, 0.094, 1.08 |
No. of reflections | 9041 |
No. of parameters | 492 |
No. of restraints | 4 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.30, −0.59 |
Computer programs: PROCESS-AUTO (Rigaku, 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Sheldrick, 1990).
Ag1—P2 | 2.4492 (7) | Ag1—O1W | 2.464 (2) |
Ag1—P1 | 2.4637 (8) | Ag1—N1 | 2.469 (2) |
P2—Ag1—P1 | 130.79 (2) | P2—Ag1—N1 | 114.57 (6) |
P2—Ag1—O1W | 105.12 (6) | P1—Ag1—N1 | 106.45 (5) |
P1—Ag1—O1W | 104.71 (6) | O1W—Ag1—N1 | 84.53 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1B···O2i | 0.83 (3) | 1.97 (3) | 2.797 (3) | 173 (3) |
O1W—H1A···O3 | 0.89 (3) | 2.10 (3) | 2.825 (4) | 137 (3) |
N1—H1C···O1ii | 0.92 (3) | 2.09 (3) | 2.972 (3) | 159 (2) |
N1—H1D···O3 | 0.83 (3) | 2.26 (3) | 2.875 (3) | 131 (3) |
Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x, −y+3/2, z+1/2. |
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In the title compound, (I), one water molecule, one 2-amino-4,5-dimethylbenzenesulfonate (L) anion and two triphenylphosphine ligands are coordinated to the metal, resulting in a distorted tetrahedral geometry for Ag (Fig. 1, Table 1). The Ag—Owater and Ag—N distances are different from those of a related compound (Li et al., 2007).
Here, the coordination ability of the amine group of L is evidently stronger than that of the sulfonate group and the latter group does not coordinate to the Ag ion. In the crystal structure of (I), adjacent molecules are interconnected by strong O—H···O and N—H···O hydrogen bonds (Table 2) to form a one-dimensional supramolecular structure (Fig. 2).