Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807022052/ng2266sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807022052/ng2266Isup2.hkl |
CCDC reference: 650614
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.036
- wR factor = 0.097
- Data-to-parameter ratio = 17.4
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 4
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 (1) 0.91 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 7
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 0 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 1 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
For studies on metal sulfonates, see: May & Shimizu (2005); Gao et al. (2005); Liu et al. (2006).
To a mixture of 2-amino-4,5-dimethylbenzenesulfonic acid (0.5 mmol) and sodium hydroxide 0.5 mmol) in water was added silver nitrate (0.5 mmol). The precipitate that formed was dissolved by ammonium hydroxide. Colorless crystals were obtained from the filtrate after being set aside, away from light, after a week (33% yield).
H atoms bonded to N atom were located in a difference map and refined freely, and with Uiso(H) = 1.2Ueq(N). H atoms bonded to C atom were positioned geometrically (C—H = 0.93 Å) and refined as riding, with Uiso(H)=1.2Ueq(carrier). The water H-atoms were located in a difference Fourier map, and were refined with distance restraints of O–H = 0.85 Å; their temperature factors were tied to those of parent atoms by a factor of 1.2.
Metal sulfonates are a class of compounds showing interesting structures and properties (May & Shimizu, 2005; Gao et al., 2005); however, the sulfonate unit itself typically exists as a non-coordinating anion (Liu et al., 2006). Indeed, in a majority of metal complexes with sulfonate counterions, the sulfonate group cannot displace water from the coordination sphere of the metal ion. This feature is also found in the present silver derivative of 2-amino-4,5-dimethylbenzenesulfonic acid.
The silvera tom in (I) is coordinated by the amino group instead; it is also linked to two water molecules in a T–shaped environment (Fig. 1). The molecules are linked through O—H···O and N—H···O hydrogen bonds (Table 2) to form a two-dimensional supramolecular structure (Fig. 2).
For studies on metal sulfonates, see: May & Shimizu (2005); Gao et al. (2005); Liu et al. (2006).
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.
[Ag(C8H10NO3S)(H2O)2] | F(000) = 688 |
Mr = 344.13 | Dx = 1.859 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2881 reflections |
a = 12.0636 (6) Å | θ = 1.7–28.2° |
b = 9.8642 (5) Å | µ = 1.81 mm−1 |
c = 10.3509 (6) Å | T = 293 K |
β = 93.263 (1)° | Block, colorless |
V = 1229.74 (11) Å3 | 0.33 × 0.27 × 0.25 mm |
Z = 4 |
Bruker APEX CCD area-detector diffractometer | 2881 independent reflections |
Radiation source: fine-focus sealed tube | 2381 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.074 |
φ and ω scans | θmax = 28.2°, θmin = 1.7° |
Absorption correction: multi-scan (SAINT; Bruker, 1998) | h = −12→16 |
Tmin = 0.542, Tmax = 0.637 | k = −12→10 |
7355 measured reflections | l = −13→13 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.036 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.097 | w = 1/[σ2(Fo2) + (0.0556P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
2881 reflections | Δρmax = 0.81 e Å−3 |
166 parameters | Δρmin = −0.67 e Å−3 |
7 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0241 (14) |
[Ag(C8H10NO3S)(H2O)2] | V = 1229.74 (11) Å3 |
Mr = 344.13 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.0636 (6) Å | µ = 1.81 mm−1 |
b = 9.8642 (5) Å | T = 293 K |
c = 10.3509 (6) Å | 0.33 × 0.27 × 0.25 mm |
β = 93.263 (1)° |
Bruker APEX CCD area-detector diffractometer | 2881 independent reflections |
Absorption correction: multi-scan (SAINT; Bruker, 1998) | 2381 reflections with I > 2σ(I) |
Tmin = 0.542, Tmax = 0.637 | Rint = 0.074 |
7355 measured reflections |
R[F2 > 2σ(F2)] = 0.036 | 7 restraints |
wR(F2) = 0.097 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.81 e Å−3 |
2881 reflections | Δρmin = −0.67 e Å−3 |
166 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 | ||
C1 | 0.7014 (2) | 0.5742 (2) | 0.2547 (2) | 0.0302 (5) | |
C2 | 0.5932 (2) | 0.5483 (3) | 0.2888 (3) | 0.0378 (6) | |
H2 | 0.5821 | 0.5069 | 0.3677 | 0.045* | |
C3 | 0.5019 (2) | 0.5827 (3) | 0.2082 (3) | 0.0414 (7) | |
C4 | 0.5188 (2) | 0.6492 (3) | 0.0924 (3) | 0.0408 (6) | |
C5 | 0.6275 (2) | 0.6730 (3) | 0.0580 (3) | 0.0386 (6) | |
H5 | 0.6386 | 0.7167 | −0.0199 | 0.046* | |
C6 | 0.7194 (2) | 0.6339 (3) | 0.1355 (2) | 0.0311 (5) | |
C7 | 0.3854 (3) | 0.5482 (5) | 0.2461 (4) | 0.0643 (10) | |
H7A | 0.3445 | 0.6304 | 0.2580 | 0.096* | |
H7B | 0.3895 | 0.4974 | 0.3253 | 0.096* | |
H7C | 0.3484 | 0.4951 | 0.1789 | 0.096* | |
C8 | 0.4235 (3) | 0.6948 (4) | 0.0021 (4) | 0.0580 (9) | |
H8A | 0.4520 | 0.7349 | −0.0738 | 0.087* | |
H8B | 0.3797 | 0.7604 | 0.0450 | 0.087* | |
H8C | 0.3780 | 0.6181 | −0.0225 | 0.087* | |
N1 | 0.8264 (2) | 0.6491 (3) | 0.0889 (2) | 0.0391 (5) | |
H2A | 0.829 (3) | 0.717 (4) | 0.040 (4) | 0.059* | |
H1A | 0.8871 (19) | 0.639 (4) | 0.126 (3) | 0.059* | |
O1 | 0.86923 (19) | 0.4162 (2) | 0.3114 (2) | 0.0460 (5) | |
O2 | 0.76622 (16) | 0.5008 (2) | 0.48734 (17) | 0.0433 (5) | |
O3 | 0.88482 (17) | 0.6513 (2) | 0.3724 (2) | 0.0467 (5) | |
S1 | 0.81314 (5) | 0.53146 (7) | 0.36498 (6) | 0.02929 (17) | |
Ag1 | 0.887415 (18) | 0.42546 (3) | −0.07922 (2) | 0.04829 (14) | |
O1W | 0.8839 (2) | 0.2714 (3) | 0.0647 (3) | 0.0591 (6) | |
HW11 | 0.836 (2) | 0.210 (3) | 0.039 (4) | 0.089* | |
HW12 | 0.9488 (15) | 0.234 (4) | 0.073 (4) | 0.089* | |
O2W | 0.8922 (2) | 0.5559 (3) | −0.2436 (3) | 0.0587 (6) | |
HW21 | 0.9604 (15) | 0.558 (4) | −0.266 (5) | 0.088* | |
HW22 | 0.872 (3) | 0.6373 (18) | −0.226 (4) | 0.088* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0332 (12) | 0.0315 (13) | 0.0256 (11) | −0.0003 (10) | 0.0005 (9) | −0.0019 (9) |
C2 | 0.0360 (14) | 0.0489 (17) | 0.0288 (13) | −0.0049 (12) | 0.0041 (10) | −0.0018 (11) |
C3 | 0.0324 (13) | 0.0505 (18) | 0.0413 (15) | −0.0021 (12) | 0.0004 (11) | −0.0114 (13) |
C4 | 0.0403 (15) | 0.0389 (16) | 0.0418 (15) | 0.0055 (12) | −0.0088 (11) | −0.0053 (12) |
C5 | 0.0478 (15) | 0.0347 (14) | 0.0325 (13) | −0.0012 (11) | −0.0036 (11) | 0.0061 (11) |
C6 | 0.0348 (12) | 0.0298 (13) | 0.0287 (12) | −0.0014 (10) | 0.0023 (9) | −0.0006 (10) |
C7 | 0.0345 (16) | 0.099 (3) | 0.059 (2) | −0.0115 (17) | 0.0026 (14) | −0.016 (2) |
C8 | 0.0491 (17) | 0.053 (2) | 0.069 (2) | 0.0071 (15) | −0.0193 (15) | 0.0019 (17) |
N1 | 0.0382 (12) | 0.0436 (15) | 0.0363 (12) | −0.0022 (11) | 0.0089 (10) | 0.0063 (10) |
O1 | 0.0530 (13) | 0.0471 (13) | 0.0378 (11) | 0.0164 (9) | 0.0015 (9) | −0.0060 (9) |
O2 | 0.0433 (10) | 0.0616 (14) | 0.0251 (9) | 0.0013 (10) | 0.0040 (8) | 0.0036 (9) |
O3 | 0.0452 (11) | 0.0460 (13) | 0.0472 (11) | −0.0137 (9) | −0.0125 (8) | 0.0066 (10) |
S1 | 0.0311 (3) | 0.0332 (3) | 0.0235 (3) | −0.0006 (2) | 0.0007 (2) | −0.0003 (2) |
Ag1 | 0.04155 (18) | 0.0547 (2) | 0.04816 (19) | 0.00171 (9) | −0.00134 (11) | 0.00677 (10) |
O1W | 0.0624 (14) | 0.0517 (14) | 0.0621 (14) | 0.0034 (12) | −0.0073 (12) | −0.0065 (12) |
O2W | 0.0590 (15) | 0.0646 (16) | 0.0526 (14) | −0.0003 (12) | 0.0043 (11) | −0.0009 (12) |
C1—C2 | 1.395 (4) | C8—H8A | 0.9600 |
C1—C6 | 1.396 (4) | C8—H8B | 0.9600 |
C1—S1 | 1.767 (3) | C8—H8C | 0.9600 |
C2—C3 | 1.386 (4) | N1—H2A | 0.85 (4) |
C2—H2 | 0.9300 | N1—H1A | 0.814 (19) |
C3—C4 | 1.392 (4) | O1—S1 | 1.450 (2) |
C3—C7 | 1.519 (4) | O2—S1 | 1.4484 (18) |
C4—C5 | 1.398 (4) | O3—S1 | 1.464 (2) |
C4—C8 | 1.509 (4) | Ag1—O1W | 2.130 (3) |
C5—C6 | 1.386 (4) | Ag1—O2W | 2.136 (3) |
C5—H5 | 0.9300 | Ag1—N1 | 2.930 (3) |
C6—N1 | 1.411 (3) | O1W—HW11 | 0.87 (3) |
C7—H7A | 0.9600 | O1W—HW12 | 0.866 (10) |
C7—H7B | 0.9600 | O2W—HW21 | 0.866 (10) |
C7—H7C | 0.9600 | O2W—HW22 | 0.864 (10) |
C2—C1—C6 | 119.7 (2) | C4—C8—H8A | 109.5 |
C2—C1—S1 | 118.9 (2) | C4—C8—H8B | 109.5 |
C6—C1—S1 | 121.4 (2) | H8A—C8—H8B | 109.5 |
C3—C2—C1 | 121.8 (3) | C4—C8—H8C | 109.5 |
C3—C2—H2 | 119.1 | H8A—C8—H8C | 109.5 |
C1—C2—H2 | 119.1 | H8B—C8—H8C | 109.5 |
C2—C3—C4 | 118.9 (3) | C6—N1—H2A | 111 (3) |
C2—C3—C7 | 120.4 (3) | C6—N1—H1A | 130 (3) |
C4—C3—C7 | 120.7 (3) | H2A—N1—H1A | 109 (4) |
C3—C4—C5 | 119.0 (2) | O2—S1—O1 | 112.63 (13) |
C3—C4—C8 | 122.0 (3) | O2—S1—O3 | 112.46 (13) |
C5—C4—C8 | 119.0 (3) | O1—S1—O3 | 111.48 (14) |
C6—C5—C4 | 122.5 (3) | O2—S1—C1 | 107.04 (12) |
C6—C5—H5 | 118.8 | O1—S1—C1 | 107.20 (12) |
C4—C5—H5 | 118.8 | O3—S1—C1 | 105.53 (12) |
C5—C6—C1 | 118.0 (2) | O1W—Ag1—O2W | 171.50 (10) |
C5—C6—N1 | 119.4 (2) | O1W—Ag1—N1 | 96.09 (9) |
C1—C6—N1 | 122.5 (2) | O2W—Ag1—N1 | 92.22 (9) |
C3—C7—H7A | 109.5 | Ag1—O1W—HW11 | 109 (3) |
C3—C7—H7B | 109.5 | Ag1—O1W—HW12 | 109 (3) |
H7A—C7—H7B | 109.5 | HW11—O1W—HW12 | 108 (2) |
C3—C7—H7C | 109.5 | Ag1—O2W—HW21 | 107 (3) |
H7A—C7—H7C | 109.5 | Ag1—O2W—HW22 | 112 (3) |
H7B—C7—H7C | 109.5 | HW21—O2W—HW22 | 109 (2) |
C6—C1—C2—C3 | −1.3 (4) | C4—C5—C6—N1 | 173.8 (3) |
S1—C1—C2—C3 | 178.3 (2) | C2—C1—C6—C5 | 3.9 (4) |
C1—C2—C3—C4 | −2.4 (4) | S1—C1—C6—C5 | −175.7 (2) |
C1—C2—C3—C7 | 177.7 (3) | C2—C1—C6—N1 | −172.8 (3) |
C2—C3—C4—C5 | 3.3 (4) | S1—C1—C6—N1 | 7.7 (4) |
C7—C3—C4—C5 | −176.8 (3) | C2—C1—S1—O2 | −11.9 (3) |
C2—C3—C4—C8 | −177.6 (3) | C6—C1—S1—O2 | 167.6 (2) |
C7—C3—C4—C8 | 2.4 (5) | C2—C1—S1—O1 | 109.1 (2) |
C3—C4—C5—C6 | −0.6 (4) | C6—C1—S1—O1 | −71.3 (2) |
C8—C4—C5—C6 | −179.8 (3) | C2—C1—S1—O3 | −131.9 (2) |
C4—C5—C6—C1 | −3.0 (4) | C6—C1—S1—O3 | 47.6 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—HW12···O3i | 0.87 (1) | 2.21 (1) | 3.067 (3) | 170 (4) |
O1W—HW11···O2ii | 0.87 (3) | 2.29 (2) | 3.119 (3) | 159 (4) |
O2W—HW21···O1iii | 0.87 (1) | 2.15 (1) | 3.013 (3) | 174 (4) |
O2W—HW22···O3iv | 0.86 (1) | 2.32 (2) | 3.131 (3) | 157 (4) |
N1—H2A···O3iv | 0.85 (4) | 2.29 (4) | 3.095 (3) | 158 (3) |
Symmetry codes: (i) −x+2, y−1/2, −z+1/2; (ii) x, −y+1/2, z−1/2; (iii) −x+2, −y+1, −z; (iv) x, −y+3/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | [Ag(C8H10NO3S)(H2O)2] |
Mr | 344.13 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 12.0636 (6), 9.8642 (5), 10.3509 (6) |
β (°) | 93.263 (1) |
V (Å3) | 1229.74 (11) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.81 |
Crystal size (mm) | 0.33 × 0.27 × 0.25 |
Data collection | |
Diffractometer | Bruker APEX CCD area-detector |
Absorption correction | Multi-scan (SAINT; Bruker, 1998) |
Tmin, Tmax | 0.542, 0.637 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7355, 2881, 2381 |
Rint | 0.074 |
(sin θ/λ)max (Å−1) | 0.665 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.036, 0.097, 1.04 |
No. of reflections | 2881 |
No. of parameters | 166 |
No. of restraints | 7 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.81, −0.67 |
Computer programs: SMART (Bruker, 1998), SMART, SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1998), SHELXTL.
Ag1—O1W | 2.130 (3) | Ag1—N1 | 2.930 (3) |
Ag1—O2W | 2.136 (3) | ||
O1W—Ag1—O2W | 171.50 (10) | O2W—Ag1—N1 | 92.22 (9) |
O1W—Ag1—N1 | 96.09 (9) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—HW12···O3i | 0.866 (10) | 2.210 (12) | 3.067 (3) | 170 (4) |
O1W—HW11···O2ii | 0.87 (3) | 2.294 (19) | 3.119 (3) | 159 (4) |
O2W—HW21···O1iii | 0.866 (10) | 2.151 (12) | 3.013 (3) | 174 (4) |
O2W—HW22···O3iv | 0.864 (10) | 2.32 (2) | 3.131 (3) | 157 (4) |
N1—H2A···O3iv | 0.85 (4) | 2.29 (4) | 3.095 (3) | 158 (3) |
Symmetry codes: (i) −x+2, y−1/2, −z+1/2; (ii) x, −y+1/2, z−1/2; (iii) −x+2, −y+1, −z; (iv) x, −y+3/2, z−1/2. |
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Metal sulfonates are a class of compounds showing interesting structures and properties (May & Shimizu, 2005; Gao et al., 2005); however, the sulfonate unit itself typically exists as a non-coordinating anion (Liu et al., 2006). Indeed, in a majority of metal complexes with sulfonate counterions, the sulfonate group cannot displace water from the coordination sphere of the metal ion. This feature is also found in the present silver derivative of 2-amino-4,5-dimethylbenzenesulfonic acid.
The silvera tom in (I) is coordinated by the amino group instead; it is also linked to two water molecules in a T–shaped environment (Fig. 1). The molecules are linked through O—H···O and N—H···O hydrogen bonds (Table 2) to form a two-dimensional supramolecular structure (Fig. 2).