Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807047897/hb2561sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807047897/hb2561Isup2.hkl |
CCDC reference: 667137
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.026
- wR factor = 0.087
- Data-to-parameter ratio = 15.3
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT420_ALERT_2_B D-H Without Acceptor O2W - H2B ... ?
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.96 PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Ag1 - O1W .. 6.76 su PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C7
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 7
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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 0 ALERT type 5 Informative message, check
An aqueous solution (10 ml) of 2-amino-4,5-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. The precipitate was dissolved by dropwise addition of an aqueous solution of NH3 (14 M). Then a methanolic solution of pyridine was added and the mixture stirred for 30 minutes. Crystals of (I) were obtained by evaporation of the solution for several days at room temperature, but the pyridine did not react with silver sulfonate.
The H atoms bonded to O were located in a difference map and were freely refined. The H atoms bonded to N were located in a difference map and their positions refined freely, with Uiso(H) = 1.5Ueq(N). The H atoms bonded to C atom were positioned geometrically (C—H = 0.93 Å) and refined as riding, with Uiso(H) = 1.2Ueq(C).
In the title compound, (I), one water molecule and one 2-amino-4,5-dimethylbenzenesulfonate (L) anion are coordinated to the metal, restulting in slightly distorted linear geometry for Ag (Table 1). The Ag—Owater distance is simiar to the equivalent value in a related compound (Han & Li, 2007).
Here, the coordination ability of the amine group of L is evidently stronger than that of sulfonate group and the latter group does not coordinate to the Ag ion. In the crystal of (I), adjacent ions and water molecules are interconnected by strong O—H···O and N—H···O hydrogen bonds (Table 2) to form a two-dimensional supramolecular network (Fig. 2).
For a related structure, see: Han & Li (2007).
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)(H2O)]·H2O | Z = 2 |
Mr = 344.13 | F(000) = 344 |
Triclinic, P1 | Dx = 1.927 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.555 (5) Å | Cell parameters from 2584 reflections |
b = 7.626 (6) Å | θ = 1.7–27.5° |
c = 12.1290 (11) Å | µ = 1.88 mm−1 |
α = 78.889 (4)° | T = 293 K |
β = 85.746 (7)° | Block, colourless |
γ = 87.754 (4)° | 0.25 × 0.23 × 0.21 mm |
V = 593.1 (7) Å3 |
Rigaku R-AXIS RAPID diffractometer | 2584 independent reflections |
Radiation source: fine-focus sealed tube | 2277 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.016 |
Detector resolution: 10.0 pixels mm-1 | θmax = 27.5°, θmin = 1.7° |
ω scans | h = −8→8 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −9→8 |
Tmin = 0.625, Tmax = 0.677 | l = −15→15 |
4856 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)] = 0.026 | Hydrogen site location: difmap and geom |
wR(F2) = 0.087 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.14 | w = 1/[σ2(Fo2) + (0.0587P)2 + 0.0536P] where P = (Fo2 + 2Fc2)/3 |
2584 reflections | (Δ/σ)max = 0.001 |
169 parameters | Δρmax = 0.51 e Å−3 |
7 restraints | Δρmin = −0.72 e Å−3 |
[Ag(C8H10NO3S)(H2O)]·H2O | γ = 87.754 (4)° |
Mr = 344.13 | V = 593.1 (7) Å3 |
Triclinic, P1 | Z = 2 |
a = 6.555 (5) Å | Mo Kα radiation |
b = 7.626 (6) Å | µ = 1.88 mm−1 |
c = 12.1290 (11) Å | T = 293 K |
α = 78.889 (4)° | 0.25 × 0.23 × 0.21 mm |
β = 85.746 (7)° |
Rigaku R-AXIS RAPID diffractometer | 2584 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 2277 reflections with I > 2σ(I) |
Tmin = 0.625, Tmax = 0.677 | Rint = 0.016 |
4856 measured reflections |
R[F2 > 2σ(F2)] = 0.026 | 7 restraints |
wR(F2) = 0.087 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.14 | Δρmax = 0.51 e Å−3 |
2584 reflections | Δρmin = −0.72 e Å−3 |
169 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 | 0.33890 (4) | 0.48750 (3) | 0.39012 (2) | 0.04069 (11) | |
C1 | 0.6290 (4) | 0.1518 (3) | 0.2095 (2) | 0.0240 (5) | |
C2 | 0.7019 (4) | 0.1533 (4) | 0.0981 (2) | 0.0295 (5) | |
H2 | 0.8337 | 0.1096 | 0.0841 | 0.035* | |
C3 | 0.5843 (5) | 0.2179 (4) | 0.0075 (2) | 0.0303 (6) | |
C4 | 0.3854 (5) | 0.2816 (4) | 0.0293 (2) | 0.0310 (6) | |
C5 | 0.3130 (4) | 0.2813 (4) | 0.1399 (2) | 0.0287 (5) | |
H5 | 0.1810 | 0.3248 | 0.1538 | 0.034* | |
C6 | 0.4314 (4) | 0.2180 (3) | 0.2310 (2) | 0.0230 (5) | |
C7 | 0.2479 (6) | 0.3485 (5) | −0.0654 (3) | 0.0456 (8) | |
H7A | 0.3104 | 0.4471 | −0.1163 | 0.068* | |
H7B | 0.1182 | 0.3869 | −0.0350 | 0.068* | |
H7C | 0.2279 | 0.2539 | −0.1052 | 0.068* | |
C8 | 0.6710 (6) | 0.2165 (5) | −0.1103 (3) | 0.0431 (7) | |
H8A | 0.5863 | 0.1468 | −0.1457 | 0.065* | |
H8B | 0.8070 | 0.1651 | −0.1083 | 0.065* | |
H8C | 0.6751 | 0.3367 | −0.1525 | 0.065* | |
N1 | 0.3465 (4) | 0.2264 (3) | 0.3425 (2) | 0.0255 (4) | |
O1 | 0.9374 (4) | −0.0551 (3) | 0.2715 (2) | 0.0460 (6) | |
O2 | 0.8951 (3) | 0.2202 (3) | 0.3429 (2) | 0.0406 (5) | |
O3 | 0.6674 (3) | −0.0227 (3) | 0.41254 (19) | 0.0393 (5) | |
O1W | 0.2817 (5) | 0.7591 (4) | 0.4077 (3) | 0.0538 (6) | |
O2W | 0.2412 (6) | 0.4253 (4) | 0.6255 (3) | 0.0702 (9) | |
S1 | 0.79500 (9) | 0.06607 (9) | 0.31726 (6) | 0.02624 (15) | |
H1A | 0.194 (7) | 0.829 (6) | 0.357 (4) | 0.078 (16)* | |
H2A | 0.210 (10) | 0.511 (8) | 0.671 (5) | 0.12 (2)* | |
H1B | 0.405 (6) | 0.836 (6) | 0.396 (4) | 0.071 (15)* | |
H2B | 0.106 (6) | 0.420 (8) | 0.621 (5) | 0.078 (17)* | |
H3A | 0.407 (11) | 0.159 (10) | 0.396 (6) | 0.039* | |
H3B | 0.227 (5) | 0.205 (5) | 0.348 (3) | 0.039* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ag1 | 0.05284 (18) | 0.03144 (15) | 0.04011 (16) | 0.00482 (10) | −0.00194 (11) | −0.01421 (10) |
C1 | 0.0262 (12) | 0.0232 (12) | 0.0226 (12) | −0.0011 (9) | 0.0000 (9) | −0.0046 (9) |
C2 | 0.0320 (13) | 0.0297 (14) | 0.0270 (14) | −0.0025 (11) | 0.0060 (10) | −0.0089 (11) |
C3 | 0.0414 (14) | 0.0280 (13) | 0.0216 (13) | −0.0058 (11) | 0.0030 (10) | −0.0059 (10) |
C4 | 0.0409 (14) | 0.0280 (14) | 0.0248 (14) | −0.0040 (11) | −0.0044 (11) | −0.0050 (11) |
C5 | 0.0302 (12) | 0.0260 (13) | 0.0309 (14) | 0.0009 (10) | −0.0028 (10) | −0.0079 (11) |
C6 | 0.0268 (12) | 0.0207 (11) | 0.0222 (12) | −0.0027 (9) | 0.0014 (9) | −0.0062 (9) |
C7 | 0.057 (2) | 0.0457 (19) | 0.0351 (17) | 0.0030 (15) | −0.0166 (14) | −0.0061 (14) |
C8 | 0.0564 (19) | 0.0478 (19) | 0.0258 (15) | −0.0063 (15) | 0.0060 (13) | −0.0110 (13) |
N1 | 0.0254 (11) | 0.0266 (11) | 0.0241 (11) | 0.0005 (9) | 0.0039 (8) | −0.0063 (9) |
O1 | 0.0447 (12) | 0.0547 (14) | 0.0387 (13) | 0.0253 (11) | −0.0037 (10) | −0.0145 (11) |
O2 | 0.0352 (10) | 0.0441 (13) | 0.0458 (13) | −0.0060 (9) | −0.0077 (9) | −0.0136 (10) |
O3 | 0.0368 (11) | 0.0471 (13) | 0.0278 (11) | −0.0036 (9) | 0.0009 (8) | 0.0076 (9) |
O1W | 0.0664 (17) | 0.0416 (14) | 0.0564 (17) | 0.0055 (13) | −0.0097 (13) | −0.0164 (12) |
O2W | 0.081 (2) | 0.0529 (18) | 0.072 (2) | 0.0036 (16) | 0.0116 (17) | −0.0081 (16) |
S1 | 0.0232 (3) | 0.0301 (3) | 0.0250 (3) | 0.0029 (2) | 0.0003 (2) | −0.0057 (3) |
Ag1—O1W | 2.139 (3) | C7—H7B | 0.9600 |
Ag1—N1 | 2.176 (3) | C7—H7C | 0.9600 |
C1—C2 | 1.397 (4) | C8—H8A | 0.9600 |
C1—C6 | 1.397 (4) | C8—H8B | 0.9600 |
C1—S1 | 1.774 (3) | C8—H8C | 0.9600 |
C2—C3 | 1.390 (4) | N1—H3B | 0.80 (3) |
C2—H2 | 0.9300 | N1—H3A | 0.86 (7) |
C3—C4 | 1.398 (4) | O1—S1 | 1.445 (2) |
C3—C8 | 1.500 (4) | O2—S1 | 1.462 (2) |
C4—C5 | 1.390 (4) | O3—S1 | 1.447 (2) |
C4—C7 | 1.511 (4) | O1W—H1B | 1.00 (4) |
C5—C6 | 1.395 (4) | O1W—H1A | 0.95 (4) |
C5—H5 | 0.9300 | O2W—H2B | 0.89 (4) |
C6—N1 | 1.436 (3) | O2W—H2A | 0.94 (4) |
C7—H7A | 0.9600 | ||
O1W—Ag1—N1 | 166.73 (10) | H7B—C7—H7C | 109.5 |
C2—C1—C6 | 119.1 (2) | C3—C8—H8A | 109.5 |
C2—C1—S1 | 117.8 (2) | C3—C8—H8B | 109.5 |
C6—C1—S1 | 123.1 (2) | H8A—C8—H8B | 109.5 |
C3—C2—C1 | 122.4 (3) | C3—C8—H8C | 109.5 |
C3—C2—H2 | 118.8 | H8A—C8—H8C | 109.5 |
C1—C2—H2 | 118.8 | H8B—C8—H8C | 109.5 |
C2—C3—C4 | 118.5 (3) | C6—N1—Ag1 | 116.43 (17) |
C2—C3—C8 | 120.0 (3) | C6—N1—H3B | 110 (3) |
C4—C3—C8 | 121.5 (3) | Ag1—N1—H3B | 101 (3) |
C5—C4—C3 | 119.2 (3) | C6—N1—H3A | 115 (5) |
C5—C4—C7 | 119.8 (3) | Ag1—N1—H3A | 103 (5) |
C3—C4—C7 | 121.0 (3) | H3B—N1—H3A | 110 (6) |
C4—C5—C6 | 122.3 (3) | Ag1—O1W—H1B | 115 (3) |
C4—C5—H5 | 118.8 | Ag1—O1W—H1A | 117 (3) |
C6—C5—H5 | 118.8 | H1B—O1W—H1A | 101 (4) |
C5—C6—C1 | 118.5 (2) | H2B—O2W—H2A | 86 (4) |
C5—C6—N1 | 118.7 (2) | O1—S1—O3 | 112.80 (15) |
C1—C6—N1 | 122.8 (2) | O1—S1—O2 | 112.65 (16) |
C4—C7—H7A | 109.5 | O3—S1—O2 | 111.73 (14) |
C4—C7—H7B | 109.5 | O1—S1—C1 | 106.17 (13) |
H7A—C7—H7B | 109.5 | O3—S1—C1 | 106.57 (13) |
C4—C7—H7C | 109.5 | O2—S1—C1 | 106.35 (14) |
H7A—C7—H7C | 109.5 | ||
C6—C1—C2—C3 | −0.2 (4) | S1—C1—C6—C5 | −179.6 (2) |
S1—C1—C2—C3 | −179.9 (2) | C2—C1—C6—N1 | −178.1 (2) |
C1—C2—C3—C4 | −0.7 (4) | S1—C1—C6—N1 | 1.5 (4) |
C1—C2—C3—C8 | 179.9 (3) | C5—C6—N1—Ag1 | −76.6 (3) |
C2—C3—C4—C5 | 1.1 (4) | C1—C6—N1—Ag1 | 102.3 (3) |
C8—C3—C4—C5 | −179.5 (3) | O1W—Ag1—N1—C6 | 66.5 (5) |
C2—C3—C4—C7 | −178.2 (3) | C2—C1—S1—O1 | −24.8 (3) |
C8—C3—C4—C7 | 1.2 (4) | C6—C1—S1—O1 | 155.5 (2) |
C3—C4—C5—C6 | −0.6 (4) | C2—C1—S1—O3 | −145.3 (2) |
C7—C4—C5—C6 | 178.7 (3) | C6—C1—S1—O3 | 35.1 (3) |
C4—C5—C6—C1 | −0.4 (4) | C2—C1—S1—O2 | 95.4 (2) |
C4—C5—C6—N1 | 178.5 (2) | C6—C1—S1—O2 | −84.3 (2) |
C2—C1—C6—C5 | 0.8 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1A···O1i | 0.95 (4) | 2.11 (4) | 3.038 (4) | 165 (4) |
O1W—H1B···O3ii | 1.00 (4) | 2.11 (4) | 3.091 (4) | 167 (4) |
O2W—H2A···O2iii | 0.94 (4) | 2.12 (6) | 2.901 (5) | 140 (6) |
N1—H3A···O3 | 0.86 (7) | 2.15 (7) | 2.843 (3) | 138 (7) |
N1—H3A···O3iv | 0.86 (7) | 2.38 (8) | 3.073 (3) | 138 (7) |
N1—H3B···O2v | 0.80 (3) | 2.18 (3) | 2.961 (4) | 165 (4) |
Symmetry codes: (i) x−1, y+1, z; (ii) x, y+1, z; (iii) −x+1, −y+1, −z+1; (iv) −x+1, −y, −z+1; (v) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | [Ag(C8H10NO3S)(H2O)]·H2O |
Mr | 344.13 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 6.555 (5), 7.626 (6), 12.1290 (11) |
α, β, γ (°) | 78.889 (4), 85.746 (7), 87.754 (4) |
V (Å3) | 593.1 (7) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.88 |
Crystal size (mm) | 0.25 × 0.23 × 0.21 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.625, 0.677 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4856, 2584, 2277 |
Rint | 0.016 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.026, 0.087, 1.14 |
No. of reflections | 2584 |
No. of parameters | 169 |
No. of restraints | 7 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.51, −0.72 |
Computer programs: PROCESS-AUTO (Rigaku, 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Sheldrick, 1990).
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1A···O1i | 0.95 (4) | 2.11 (4) | 3.038 (4) | 165 (4) |
O1W—H1B···O3ii | 1.00 (4) | 2.11 (4) | 3.091 (4) | 167 (4) |
O2W—H2A···O2iii | 0.94 (4) | 2.12 (6) | 2.901 (5) | 140 (6) |
N1—H3A···O3 | 0.86 (7) | 2.15 (7) | 2.843 (3) | 138 (7) |
N1—H3A···O3iv | 0.86 (7) | 2.38 (8) | 3.073 (3) | 138 (7) |
N1—H3B···O2v | 0.80 (3) | 2.18 (3) | 2.961 (4) | 165 (4) |
Symmetry codes: (i) x−1, y+1, z; (ii) x, y+1, z; (iii) −x+1, −y+1, −z+1; (iv) −x+1, −y, −z+1; (v) x−1, y, z. |
In the title compound, (I), one water molecule and one 2-amino-4,5-dimethylbenzenesulfonate (L) anion are coordinated to the metal, restulting in slightly distorted linear geometry for Ag (Table 1). The Ag—Owater distance is simiar to the equivalent value in a related compound (Han & Li, 2007).
Here, the coordination ability of the amine group of L is evidently stronger than that of sulfonate group and the latter group does not coordinate to the Ag ion. In the crystal of (I), adjacent ions and water molecules are interconnected by strong O—H···O and N—H···O hydrogen bonds (Table 2) to form a two-dimensional supramolecular network (Fig. 2).