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The title compound, [Ag(C5H5N)(H2O)](C6H4Cl2NO3S)·2H2O, has a mononuclear structure in which the Ag+ cation is two-coordinated by one N atom from a pyridine mol­ecule and one O atom from a water mol­ecule. The 4-amino-2,5-dichloro­benzene­sulfonate anion does not coordinate to the Ag atom, but acts as a counterion. Inter­molecular O—H...O hydrogen bonds link the ions and water molecules.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680702329X/at2291sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680702329X/at2291Isup2.hkl
Contains datablock I

CCDC reference: 650682

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.010 Å
  • R factor = 0.048
  • wR factor = 0.093
  • Data-to-parameter ratio = 17.1

checkCIF/PLATON results

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Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 11
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 28.30 From the CIF: _reflns_number_total 3963 Count of symmetry unique reflns 2331 Completeness (_total/calc) 170.01% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1632 Fraction of Friedel pairs measured 0.700 Are heavy atom types Z>Si present yes PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 13
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 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 0 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

Comment top

The structure of the title compound, (I) (Fig. 1), containing a pyridine molecule, three water molecules and 2,5-dichloro-4-amino-benzenesulfonate (L) anion is described. In (I), pyridine and water molecule are coordinated to the metal, resulting in a slightly distorted linear coordination geometry for Ag (Table 1). Atoms Ag1, N1 and O1W are almost linear and the angle of N1—Ag1—O1W is 172.07°. The Ag—Npyrindine and Ag—O1W distances are 2.148 (6)Å and 2.162 (5) Å, respectively; the Ag—Npyrindine distance is similar to the equivalent value in related compound (Li et al., 2006). 2,5-Dichloro-4-amino-benzenesulfonate anion does not coordinate with Ag atom, but acts as counterions..

In (I), the coordination ability of the oxygen atom of guest water molecule is evidently stronger than that of sulfonate group and the latter group does not coordinate to the Ag ion. Adjacent molecules of L are interconnected by strong O—H···O hydrogen-bonding interactions between uncoordinated sulfonate O atoms and uncoordinated water molecules (Table 2). Thus, the compound forms a one-dimensional anions chain through extensive intermolecular hydrogen bonding (Fig. 2).

Related literature top

The related compound, [Ag(HL3)(Pic)2] (HL3 = p-hydroxybenzenesulfonic acid, Pic = β-picoline), has a dimeric structure and each silver cation is coordinated by two nitrogen atoms from two different β-picoline ligands and two oxygen atoms from two HL3 anions with Ag—N distances of 2.168 (3) and 2.163 (3) Å (Li et al., 2006). For related literature, see: Bruker (1997); Sheldrick (1996).

Experimental top

An aqueous solution (10 ml) of 2,5-dichloro-4-amino-benzenesulfonic acid (0.121 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; pyridine (0.0395 g, 0.5 mmol) in methanol (5 ml) was then added and a white precipitate formed. The precipitate was dissolved by dropwise addition of an aqueous solution of NH3 (14 M). Crystals of (I) were obtained by evaporation of the solution for several days at room temperature.

Refinement top

All H atoms on C atoms were positioned geometrically and refined as riding, with C—H = 0.93 ° A and Uiso(H) = 1.2 or 1.5 times Ueq(C). The amino H atoms were located in a difference Fourier map and refined isotropically. The water H atoms were located in a difference Fourier map and refined with Uiso(H) = 1.5Ueq(O).

Structure description top

The structure of the title compound, (I) (Fig. 1), containing a pyridine molecule, three water molecules and 2,5-dichloro-4-amino-benzenesulfonate (L) anion is described. In (I), pyridine and water molecule are coordinated to the metal, resulting in a slightly distorted linear coordination geometry for Ag (Table 1). Atoms Ag1, N1 and O1W are almost linear and the angle of N1—Ag1—O1W is 172.07°. The Ag—Npyrindine and Ag—O1W distances are 2.148 (6)Å and 2.162 (5) Å, respectively; the Ag—Npyrindine distance is similar to the equivalent value in related compound (Li et al., 2006). 2,5-Dichloro-4-amino-benzenesulfonate anion does not coordinate with Ag atom, but acts as counterions..

In (I), the coordination ability of the oxygen atom of guest water molecule is evidently stronger than that of sulfonate group and the latter group does not coordinate to the Ag ion. Adjacent molecules of L are interconnected by strong O—H···O hydrogen-bonding interactions between uncoordinated sulfonate O atoms and uncoordinated water molecules (Table 2). Thus, the compound forms a one-dimensional anions chain through extensive intermolecular hydrogen bonding (Fig. 2).

The related compound, [Ag(HL3)(Pic)2] (HL3 = p-hydroxybenzenesulfonic acid, Pic = β-picoline), has a dimeric structure and each silver cation is coordinated by two nitrogen atoms from two different β-picoline ligands and two oxygen atoms from two HL3 anions with Ag—N distances of 2.168 (3) and 2.163 (3) Å (Li et al., 2006). For related literature, see: Bruker (1997); Sheldrick (1996).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); 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.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.
[Figure 2] Fig. 2. One-dimensional chain of (I), formed through hydrogen-bonding (dashed lines) interactions.The atoms not involved in hydrogen bonding have been omitted.
Aquapyridinesilver(I) 4-amino-2,5-dichlorobenzenesulfonate dihydrate top
Crystal data top
[Ag(C5H5N)(H2O)](C6H4Cl2NO3S)·2H2OF(000) = 480
Mr = 482.08Dx = 1.835 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 3963 reflections
a = 9.325 (2) Åθ = 1.7–28.3°
b = 7.6101 (13) ŵ = 1.61 mm1
c = 12.3466 (19) ÅT = 294 K
β = 95.365 (13)°Block, white
V = 872.3 (3) Å30.21 × 0.20 × 0.18 mm
Z = 2
Data collection top
Bruker SMART APEX CCD
diffractometer
3963 independent reflections
Radiation source: fine-focus sealed tube2001 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.066
phi and ω scansθmax = 28.3°, θmin = 1.7°
Absorption correction: empirical (using intensity measurements)
SADABS (Sheldrick, 1996)
h = 127
Tmin = 0.705, Tmax = 0.75k = 108
6338 measured reflectionsl = 1615
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.093 w = 1/[σ2(Fo2) + (0.0301P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.80(Δ/σ)max = 0.001
3963 reflectionsΔρmax = 0.41 e Å3
232 parametersΔρmin = 0.38 e Å3
13 restraintsAbsolute structure: Flack (1983), 1632 Freidel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.06 (4)
Crystal data top
[Ag(C5H5N)(H2O)](C6H4Cl2NO3S)·2H2OV = 872.3 (3) Å3
Mr = 482.08Z = 2
Monoclinic, P21Mo Kα radiation
a = 9.325 (2) ŵ = 1.61 mm1
b = 7.6101 (13) ÅT = 294 K
c = 12.3466 (19) Å0.21 × 0.20 × 0.18 mm
β = 95.365 (13)°
Data collection top
Bruker SMART APEX CCD
diffractometer
3963 independent reflections
Absorption correction: empirical (using intensity measurements)
SADABS (Sheldrick, 1996)
2001 reflections with I > 2σ(I)
Tmin = 0.705, Tmax = 0.75Rint = 0.066
6338 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.048H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.093Δρmax = 0.41 e Å3
S = 0.80Δρmin = 0.38 e Å3
3963 reflectionsAbsolute structure: Flack (1983), 1632 Freidel pairs
232 parametersAbsolute structure parameter: 0.06 (4)
13 restraints
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
Ag10.14273 (6)0.76552 (8)0.76877 (5)0.0596 (2)
C10.6240 (7)0.2943 (9)0.8378 (4)0.0313 (15)
C20.5928 (7)0.4023 (8)0.9251 (5)0.0312 (16)
C30.4540 (8)0.4444 (8)0.9427 (5)0.0338 (16)
H30.43780.51361.00250.041*
C40.3366 (7)0.3871 (8)0.8744 (5)0.0311 (16)
C50.3702 (6)0.2774 (10)0.7844 (4)0.0354 (15)
C60.5080 (6)0.2342 (9)0.7697 (5)0.0319 (16)
H60.52530.16150.71180.038*
C70.4620 (8)0.7543 (13)0.7271 (5)0.0561 (18)
H70.47490.80990.79440.067*
C80.5811 (9)0.7031 (12)0.6767 (8)0.075 (3)
H80.67310.72130.71080.090*
C90.5637 (11)0.6263 (13)0.5774 (8)0.077 (3)
H90.64330.59530.54140.092*
C100.4290 (11)0.5955 (13)0.5315 (7)0.075 (3)
H100.41430.53860.46470.090*
C110.3146 (10)0.6493 (12)0.5847 (6)0.069 (3)
H110.22220.63130.55130.083*
N10.1990 (7)0.4291 (8)0.8898 (6)0.0493 (17)
N20.3290 (6)0.7260 (8)0.6816 (4)0.0474 (16)
O10.8803 (5)0.3887 (6)0.7913 (4)0.0484 (13)
O20.7831 (5)0.1100 (6)0.7236 (4)0.0512 (14)
O30.8638 (5)0.1433 (6)0.9135 (4)0.0504 (14)
O1W0.0366 (6)0.7715 (10)0.8677 (4)0.0765 (15)
O2W0.9509 (9)0.0802 (8)0.5812 (5)0.0661 (19)
O3W0.9266 (11)0.5599 (7)0.5930 (6)0.076 (2)
S10.80197 (17)0.2296 (2)0.81471 (13)0.0344 (4)
Cl10.7303 (2)0.4896 (2)1.01407 (15)0.0508 (5)
Cl20.2283 (2)0.1997 (2)0.69835 (16)0.0566 (6)
H1A0.010 (7)0.759 (12)0.945 (3)0.085*
H1B0.107 (7)0.680 (9)0.867 (6)0.085*
H2A0.909 (8)0.178 (7)0.586 (5)0.085*
H2B0.981 (10)0.055 (10)0.641 (4)0.085*
H1N0.123 (7)0.383 (10)0.858 (6)0.085*
H3A0.963 (10)0.506 (10)0.543 (5)0.085*
H3B0.902 (10)0.494 (9)0.633 (5)0.085*
H2N0.173 (8)0.472 (11)0.943 (5)0.085*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ag10.0553 (4)0.0648 (4)0.0599 (4)0.0080 (4)0.0108 (3)0.0016 (4)
C10.041 (4)0.027 (4)0.027 (3)0.005 (3)0.006 (3)0.005 (3)
C20.031 (4)0.029 (4)0.033 (4)0.002 (3)0.001 (3)0.001 (3)
C30.046 (5)0.028 (4)0.028 (4)0.005 (3)0.005 (3)0.005 (3)
C40.029 (4)0.029 (4)0.038 (4)0.003 (3)0.014 (3)0.011 (3)
C50.034 (4)0.032 (3)0.039 (3)0.008 (4)0.000 (3)0.002 (4)
C60.035 (4)0.032 (4)0.030 (3)0.002 (4)0.007 (3)0.001 (3)
C70.052 (5)0.062 (5)0.052 (4)0.003 (6)0.002 (4)0.002 (6)
C80.049 (6)0.089 (9)0.086 (7)0.004 (6)0.004 (5)0.014 (6)
C90.066 (7)0.095 (7)0.074 (7)0.002 (6)0.033 (6)0.000 (6)
C100.079 (8)0.093 (7)0.057 (6)0.014 (6)0.024 (6)0.015 (5)
C110.059 (6)0.100 (7)0.046 (5)0.003 (5)0.002 (5)0.007 (5)
N10.038 (4)0.048 (4)0.062 (5)0.012 (3)0.004 (3)0.005 (3)
N20.051 (4)0.048 (4)0.043 (3)0.001 (3)0.003 (3)0.001 (3)
O10.040 (3)0.045 (3)0.061 (3)0.011 (3)0.011 (3)0.004 (3)
O20.042 (3)0.058 (3)0.054 (3)0.008 (3)0.008 (3)0.030 (3)
O30.053 (3)0.046 (3)0.051 (3)0.025 (3)0.001 (3)0.011 (2)
O1W0.078 (4)0.073 (4)0.080 (3)0.002 (5)0.020 (3)0.001 (5)
O2W0.083 (5)0.063 (4)0.057 (4)0.002 (4)0.026 (4)0.000 (3)
O3W0.114 (7)0.054 (4)0.064 (5)0.014 (4)0.037 (4)0.004 (3)
S10.0331 (9)0.0353 (11)0.0355 (9)0.0011 (8)0.0070 (7)0.0034 (8)
Cl10.0497 (13)0.0557 (12)0.0460 (11)0.0030 (10)0.0013 (9)0.0191 (9)
Cl20.0391 (11)0.0650 (14)0.0631 (12)0.0029 (10)0.0087 (10)0.0129 (10)
Geometric parameters (Å, º) top
Ag1—N22.148 (6)C8—H80.9300
Ag1—O1W2.162 (5)C9—C101.349 (12)
C1—C61.384 (8)C9—H90.9300
C1—C21.408 (8)C10—C111.367 (11)
C1—S11.779 (6)C10—H100.9300
C2—C31.371 (9)C11—N21.327 (9)
C2—Cl11.740 (7)C11—H110.9300
C3—C41.388 (9)N1—H1N0.85 (4)
C3—H30.9300N1—H2N0.79 (4)
C4—N11.353 (8)O1—S11.457 (5)
C4—C51.447 (9)O2—S11.445 (4)
C5—C61.355 (8)O3—S11.456 (4)
C5—Cl21.722 (6)O1W—H1A0.97 (4)
C6—H60.9300O1W—H1B0.96 (4)
C7—N21.330 (8)O2W—H2A0.85 (4)
C7—C81.380 (10)O2W—H2B0.79 (4)
C7—H70.9300O3W—H3A0.84 (4)
C8—C91.355 (11)O3W—H3B0.76 (4)
N2—Ag1—O1W172.1 (3)C10—C9—H9120.5
C6—C1—C2116.9 (6)C8—C9—H9120.5
C6—C1—S1119.9 (5)C9—C10—C11118.9 (9)
C2—C1—S1123.1 (5)C9—C10—H10120.5
C3—C2—C1121.6 (6)C11—C10—H10120.5
C3—C2—Cl1117.5 (5)N2—C11—C10123.2 (8)
C1—C2—Cl1120.9 (5)N2—C11—H11118.4
C2—C3—C4122.2 (6)C10—C11—H11118.4
C2—C3—H3118.9C4—N1—H1N126 (5)
C4—C3—H3118.9C4—N1—H2N125 (6)
N1—C4—C3123.0 (6)H1N—N1—H2N105 (5)
N1—C4—C5121.4 (6)C11—N2—C7117.6 (7)
C3—C4—C5115.7 (6)C11—N2—Ag1119.7 (6)
C6—C5—C4121.3 (6)C7—N2—Ag1122.1 (5)
C6—C5—Cl2121.1 (5)Ag1—O1W—H1A115 (4)
C4—C5—Cl2117.6 (5)Ag1—O1W—H1B123 (5)
C5—C6—C1122.4 (6)H1A—O1W—H1B93 (4)
C5—C6—H6118.8H2A—O2W—H2B106 (5)
C1—C6—H6118.8H3A—O3W—H3B109 (5)
N2—C7—C8121.5 (8)O2—S1—O3112.2 (3)
N2—C7—H7119.3O2—S1—O1113.3 (3)
C8—C7—H7119.3O3—S1—O1112.0 (3)
C9—C8—C7119.8 (8)O2—S1—C1104.5 (3)
C9—C8—H8120.1O3—S1—C1107.0 (3)
C7—C8—H8120.1O1—S1—C1107.1 (3)
C10—C9—C8118.9 (9)
C6—C1—C2—C30.8 (9)S1—C1—C6—C5179.1 (6)
S1—C1—C2—C3177.6 (5)N2—C7—C8—C91.8 (14)
C6—C1—C2—Cl1178.5 (5)C7—C8—C9—C102.5 (14)
S1—C1—C2—Cl13.2 (8)C8—C9—C10—C112.7 (14)
C1—C2—C3—C41.7 (10)C9—C10—C11—N22.2 (14)
Cl1—C2—C3—C4177.6 (5)C10—C11—N2—C71.5 (13)
C2—C3—C4—N1179.1 (7)C10—C11—N2—Ag1169.8 (7)
C2—C3—C4—C51.1 (9)C8—C7—N2—C111.2 (12)
N1—C4—C5—C6179.4 (7)C8—C7—N2—Ag1169.8 (7)
C3—C4—C5—C60.3 (10)C6—C1—S1—O22.8 (6)
N1—C4—C5—Cl20.8 (9)C2—C1—S1—O2175.5 (5)
C3—C4—C5—Cl2179.0 (5)C6—C1—S1—O3122.0 (5)
C4—C5—C6—C11.2 (11)C2—C1—S1—O356.3 (6)
Cl2—C5—C6—C1179.8 (5)C6—C1—S1—O1117.7 (5)
C2—C1—C6—C50.7 (9)C2—C1—S1—O164.0 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2W—H2B···O20.79 (4)2.53 (10)2.855 (8)106 (8)
O2W—H2A···O3Wi0.85 (4)2.00 (6)2.753 (8)147 (8)
O3W—H3B···O10.76 (4)2.14 (5)2.842 (8)155 (9)
O3W—H3A···O2Wii0.84 (4)1.92 (4)2.744 (7)171 (8)
Symmetry codes: (i) x, y1, z; (ii) x+2, y+1/2, z+1.

Experimental details

Crystal data
Chemical formula[Ag(C5H5N)(H2O)](C6H4Cl2NO3S)·2H2O
Mr482.08
Crystal system, space groupMonoclinic, P21
Temperature (K)294
a, b, c (Å)9.325 (2), 7.6101 (13), 12.3466 (19)
β (°) 95.365 (13)
V3)872.3 (3)
Z2
Radiation typeMo Kα
µ (mm1)1.61
Crystal size (mm)0.21 × 0.20 × 0.18
Data collection
DiffractometerBruker SMART APEX CCD
Absorption correctionEmpirical (using intensity measurements)
SADABS (Sheldrick, 1996)
Tmin, Tmax0.705, 0.75
No. of measured, independent and
observed [I > 2σ(I)] reflections
6338, 3963, 2001
Rint0.066
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.093, 0.80
No. of reflections3963
No. of parameters232
No. of restraints13
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.41, 0.38
Absolute structureFlack (1983), 1632 Freidel pairs
Absolute structure parameter0.06 (4)

Computer programs: SMART (Bruker, 1997), SMART, SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Sheldrick, 1990), SHELXL97.

Selected geometric parameters (Å, º) top
Ag1—N22.148 (6)Ag1—O1W2.162 (5)
N2—Ag1—O1W172.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2W—H2B···O20.79 (4)2.53 (10)2.855 (8)106 (8)
O2W—H2A···O3Wi0.85 (4)2.00 (6)2.753 (8)147 (8)
O3W—H3B···O10.76 (4)2.14 (5)2.842 (8)155 (9)
O3W—H3A···O2Wii0.84 (4)1.92 (4)2.744 (7)171 (8)
Symmetry codes: (i) x, y1, z; (ii) x+2, y+1/2, z+1.
 

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