Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
The title compound, [Ag(C6H5ClNO3S)(C6H8N2)]n, has a chain structure, where the AgI cation is four-coordinated by three N atoms from two different 2,5-dimethyl­pyrazine mol­ecules and an NH2 group of a 2-amino-5-chloro­benzene­sulfonate anion, and one sulfonate O atom. N—H...O hydrogen bonds stabilize the structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807048957/bt2528sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807048957/bt2528Isup2.hkl
Contains datablock I

CCDC reference: 667141

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.025
  • wR factor = 0.053
  • Data-to-parameter ratio = 14.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
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 27.48 From the CIF: _reflns_number_total 2935 Count of symmetry unique reflns 1772 Completeness (_total/calc) 165.63% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1163 Fraction of Friedel pairs measured 0.656 Are heavy atom types Z>Si present yes PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 4
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 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

The design and synthesis of silver(I) sulfonates have attracted intense interests of chemists (Cote & Shimizu, 2003). Generally, the structure motifs of most silver(I) sulfonates observed is a two-dimensional layer, which is similar to that of metal phosphonates (Liu et al., 2007). So far, some silver(I) sulfonate compounds modified by nitrogen-based secondary ligands have been reported (Li et al., 2006). Herein, we present a new sulfonate coordination polymer, namely [Ag(dmp)(L)] where dmp = 2,5-dimethylpyrazine and HL= 2-amino-5-chlorobenzenesulfonic acid.

In the title compound the AgI cation is four-coordinated by three N atoms from two different 2,5-dimethylprazine molecules and a –NH2 group of 2-amino-5-chlorobenzenesulfonate anion, and one sulfonate O atom (Fig. 1). The Ag—O (sulfonate) distance is near to that in a related compound (Liu et al., 2007). The dmp ligand links two neighboring AgI atoms, forming a chain structure. The L ligands are attached on one side of the chains in a chelating mode. Finally, the molecules are linked through N—H···O hydrogen bonds (Table 1).

Related literature top

For studies on silver sulfonates, see Liu et al. (2007).

For related literature, see: Cote & Shimizu (2003); Li et al. (2006).

Experimental top

An aqueous solution (8 ml) of 2-amino-5-chlorobenzenesulfonic acid (1 mmol) was added to solid Ag2CO3 (0.5 mmol) and stirred for several minutes until no further CO2 was given off. The 2,5-dimethylprazine (1 mmol) was then added and a precipitate was formed. The precipitate was dissolved by ammonium hydroxide. Crystals were obtained by evaporation of the solution for several days at room temperature.

Refinement top

H atoms bonded to N atom were located in a difference map and refined with distance restraints of N–H = 0.85±0.01 Å and H···H = 1.3±0.01 Å, and with Uiso(H) = 1.2Ueq(N). H atoms of C atoms were positioned geometrically (C—H = 0.93 Å) and refined as riding, with Uiso(H)=1.2Ueq(C). The methyl groups were allowed to rotate but not to tip.

Structure description top

The design and synthesis of silver(I) sulfonates have attracted intense interests of chemists (Cote & Shimizu, 2003). Generally, the structure motifs of most silver(I) sulfonates observed is a two-dimensional layer, which is similar to that of metal phosphonates (Liu et al., 2007). So far, some silver(I) sulfonate compounds modified by nitrogen-based secondary ligands have been reported (Li et al., 2006). Herein, we present a new sulfonate coordination polymer, namely [Ag(dmp)(L)] where dmp = 2,5-dimethylpyrazine and HL= 2-amino-5-chlorobenzenesulfonic acid.

In the title compound the AgI cation is four-coordinated by three N atoms from two different 2,5-dimethylprazine molecules and a –NH2 group of 2-amino-5-chlorobenzenesulfonate anion, and one sulfonate O atom (Fig. 1). The Ag—O (sulfonate) distance is near to that in a related compound (Liu et al., 2007). The dmp ligand links two neighboring AgI atoms, forming a chain structure. The L ligands are attached on one side of the chains in a chelating mode. Finally, the molecules are linked through N—H···O hydrogen bonds (Table 1).

For studies on silver sulfonates, see Liu et al. (2007).

For related literature, see: Cote & Shimizu (2003); Li et al. (2006).

Computing details top

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).

Figures top
[Figure 1] Fig. 1. The structure of the title compound, showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Symmetry code: (i) 0.5 - x, y - 1/2, 1/2 + z.
[Figure 2] Fig. 2. View of the chain structure.
catena-Poly[[(2-amino-5-chlorobenzenesulfonato-κ2N,O)silver(I)]-µ- 2,5-dimethylpyrazine-κ2N:N'] top
Crystal data top
[Ag(C6H5ClNO3S)(C6H8N2)]F(000) = 840
Mr = 422.63Dx = 1.953 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 10124 reflections
a = 14.671 (3) Åθ = 3.0–27.5°
b = 11.947 (2) ŵ = 1.75 mm1
c = 8.2025 (16) ÅT = 293 K
V = 1437.7 (5) Å3Platelet, colorless
Z = 40.32 × 0.23 × 0.06 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer
2935 independent reflections
Radiation source: fine-focus sealed tube2638 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
Detector resolution: 10.0 pixels mm-1θmax = 27.5°, θmin = 3.0°
ω scansh = 1819
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
k = 1515
Tmin = 0.653, Tmax = 0.906l = 108
11475 measured reflections
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)] = 0.025H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.053 w = 1/[σ2(Fo2) + (0.0213P)2 + 0.3336P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
2935 reflectionsΔρmax = 0.37 e Å3
200 parametersΔρmin = 0.33 e Å3
4 restraintsAbsolute structure: Flack (1983), 1172 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.03 (3)
Crystal data top
[Ag(C6H5ClNO3S)(C6H8N2)]V = 1437.7 (5) Å3
Mr = 422.63Z = 4
Orthorhombic, Pna21Mo Kα radiation
a = 14.671 (3) ŵ = 1.75 mm1
b = 11.947 (2) ÅT = 293 K
c = 8.2025 (16) Å0.32 × 0.23 × 0.06 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer
2935 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
2638 reflections with I > 2σ(I)
Tmin = 0.653, Tmax = 0.906Rint = 0.034
11475 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.025H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.053Δρmax = 0.37 e Å3
S = 1.05Δρmin = 0.33 e Å3
2935 reflectionsAbsolute structure: Flack (1983), 1172 Friedel pairs
200 parametersAbsolute structure parameter: 0.03 (3)
4 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
Ag10.243272 (14)0.646505 (19)0.76476 (5)0.03722 (8)
S10.07812 (5)0.76842 (6)1.01266 (12)0.03172 (17)
Cl10.08916 (7)0.48754 (8)1.52741 (16)0.0547 (3)
O30.08442 (16)0.7030 (2)0.8637 (3)0.0456 (6)
O10.01398 (14)0.77287 (18)1.0795 (3)0.0389 (6)
N20.24774 (17)0.7932 (2)0.5917 (4)0.0280 (6)
C100.3268 (2)0.8382 (3)0.5426 (4)0.0305 (7)
N10.28661 (17)0.7479 (2)1.0269 (4)0.0348 (6)
O20.12086 (18)0.87723 (19)1.0001 (4)0.0523 (8)
C10.14351 (19)0.6928 (2)1.1575 (4)0.0261 (6)
C60.23964 (19)0.6899 (3)1.1469 (4)0.0291 (7)
C70.1702 (2)0.8401 (3)0.5413 (4)0.0312 (7)
H70.11520.81040.57720.037*
C20.09859 (17)0.6303 (2)1.2728 (6)0.0287 (6)
H20.03530.63221.27890.034*
C30.1481 (2)0.5643 (3)1.3803 (4)0.0316 (7)
C40.2415 (2)0.5588 (3)1.3718 (5)0.0355 (8)
H40.27370.51361.44390.043*
C50.28739 (18)0.6210 (2)1.2549 (7)0.0340 (7)
H50.35060.61691.24850.041*
C110.4135 (2)0.7864 (3)0.5991 (6)0.0501 (10)
H11A0.41740.79170.71570.075*
H11B0.46410.82500.55080.075*
H11C0.41480.70910.56730.075*
C80.1686 (2)0.9322 (3)0.4367 (4)0.0280 (7)
N30.24766 (18)0.9781 (2)0.3873 (4)0.0288 (6)
C120.0810 (2)0.9820 (3)0.3801 (6)0.0438 (9)
H12A0.07311.05440.42910.066*
H12B0.03140.93420.41130.066*
H12C0.08210.98960.26360.066*
C90.3255 (2)0.9311 (3)0.4415 (4)0.0335 (8)
H90.38070.96240.40970.040*
HN10.3438 (7)0.752 (2)1.029 (4)0.027 (8)*
HN20.272 (2)0.8154 (13)1.015 (8)0.070 (16)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ag10.04065 (13)0.03172 (11)0.03929 (14)0.00103 (10)0.0046 (2)0.01531 (14)
S10.0169 (3)0.0350 (4)0.0432 (5)0.0006 (3)0.0003 (4)0.0113 (4)
Cl10.0565 (6)0.0521 (5)0.0554 (6)0.0058 (4)0.0073 (5)0.0249 (5)
O30.0299 (13)0.0725 (19)0.0345 (14)0.0059 (12)0.0044 (11)0.0053 (13)
O10.0198 (10)0.0398 (13)0.0572 (18)0.0037 (9)0.0060 (10)0.0130 (11)
N20.0311 (13)0.0232 (13)0.0299 (15)0.0038 (11)0.0025 (12)0.0020 (11)
C100.0270 (15)0.0314 (17)0.0332 (19)0.0036 (12)0.0011 (14)0.0031 (13)
N10.0170 (12)0.0399 (17)0.0477 (19)0.0027 (11)0.0030 (14)0.0003 (15)
O20.0325 (13)0.0378 (15)0.087 (2)0.0034 (10)0.0017 (15)0.0254 (15)
C10.0207 (14)0.0237 (15)0.0340 (18)0.0016 (12)0.0033 (13)0.0013 (12)
C60.0209 (14)0.0313 (16)0.0353 (18)0.0039 (13)0.0010 (14)0.0038 (13)
C70.0286 (16)0.0260 (16)0.039 (2)0.0036 (13)0.0015 (15)0.0016 (13)
C20.0229 (11)0.0259 (13)0.0374 (17)0.0007 (10)0.000 (2)0.0027 (15)
C30.0365 (17)0.0261 (16)0.0322 (18)0.0014 (13)0.0031 (15)0.0021 (13)
C40.0373 (18)0.0335 (18)0.0358 (19)0.0115 (14)0.0049 (16)0.0030 (15)
C50.0207 (12)0.0389 (16)0.0424 (18)0.0078 (11)0.008 (2)0.007 (2)
C110.0356 (19)0.052 (2)0.063 (3)0.0027 (16)0.0062 (19)0.0296 (19)
C80.0298 (15)0.0229 (16)0.0314 (17)0.0013 (13)0.0028 (13)0.0026 (12)
N30.0326 (14)0.0246 (13)0.0293 (15)0.0002 (11)0.0032 (12)0.0032 (11)
C120.0335 (18)0.038 (2)0.060 (3)0.0036 (15)0.0027 (18)0.0071 (17)
C90.0277 (15)0.0351 (19)0.038 (2)0.0035 (14)0.0037 (15)0.0085 (14)
Geometric parameters (Å, º) top
Ag1—N3i2.253 (3)C7—C81.396 (4)
Ag1—N22.256 (3)C7—H70.9300
Ag1—N12.549 (3)C2—C31.388 (5)
Ag1—O32.559 (2)C2—H20.9300
S1—O21.447 (2)C3—C41.372 (5)
S1—O31.453 (3)C4—C51.388 (6)
S1—O11.459 (2)C4—H40.9300
S1—C11.774 (3)C5—H50.9300
Cl1—C31.746 (3)C11—H11A0.9600
N2—C71.334 (4)C11—H11B0.9600
N2—C101.341 (4)C11—H11C0.9600
C10—C91.385 (4)C8—N31.345 (4)
C10—C111.488 (5)C8—C121.491 (4)
N1—C61.387 (5)N3—C91.347 (4)
N1—HN10.841 (10)N3—Ag1ii2.253 (3)
N1—HN20.840 (10)C12—H12A0.9600
C1—C21.374 (5)C12—H12B0.9600
C1—C61.413 (4)C12—H12C0.9600
C6—C51.397 (6)C9—H90.9300
N3i—Ag1—N2166.54 (11)C1—C2—C3119.7 (3)
N3i—Ag1—N191.92 (10)C1—C2—H2120.2
N2—Ag1—N198.89 (10)C3—C2—H2120.2
N3i—Ag1—O398.52 (9)C4—C3—C2121.2 (3)
N2—Ag1—O391.20 (9)C4—C3—Cl1120.3 (3)
N1—Ag1—O380.45 (8)C2—C3—Cl1118.5 (3)
O2—S1—O3113.29 (18)C3—C4—C5119.6 (3)
O2—S1—O1113.28 (15)C3—C4—H4120.2
O3—S1—O1113.24 (15)C5—C4—H4120.2
O2—S1—C1105.71 (16)C4—C5—C6120.7 (3)
O3—S1—C1104.77 (15)C4—C5—H5119.7
O1—S1—C1105.53 (15)C6—C5—H5119.7
S1—O3—Ag1117.81 (13)C10—C11—H11A109.5
C7—N2—C10118.4 (3)C10—C11—H11B109.5
C7—N2—Ag1119.8 (2)H11A—C11—H11B109.5
C10—N2—Ag1121.7 (2)C10—C11—H11C109.5
N2—C10—C9119.2 (3)H11A—C11—H11C109.5
N2—C10—C11118.6 (3)H11B—C11—H11C109.5
C9—C10—C11122.1 (3)N3—C8—C7119.5 (3)
C6—N1—Ag1103.7 (2)N3—C8—C12119.2 (3)
C6—N1—HN1120 (2)C7—C8—C12121.4 (3)
Ag1—N1—HN1107 (2)C8—N3—C9117.5 (3)
C6—N1—HN2116 (4)C8—N3—Ag1ii123.3 (2)
Ag1—N1—HN2107 (4)C9—N3—Ag1ii118.0 (2)
HN1—N1—HN2102.0 (15)C8—C12—H12A109.5
C2—C1—C6120.5 (3)C8—C12—H12B109.5
C2—C1—S1118.6 (2)H12A—C12—H12B109.5
C6—C1—S1120.8 (3)C8—C12—H12C109.5
N1—C6—C5119.7 (3)H12A—C12—H12C109.5
N1—C6—C1121.8 (3)H12B—C12—H12C109.5
C5—C6—C1118.4 (3)N3—C9—C10122.9 (3)
N2—C7—C8122.4 (3)N3—C9—H9118.5
N2—C7—H7118.8C10—C9—H9118.5
C8—C7—H7118.8
O2—S1—O3—Ag163.33 (19)Ag1—N1—C6—C167.9 (3)
O1—S1—O3—Ag1165.89 (13)C2—C1—C6—N1176.9 (3)
C1—S1—O3—Ag151.40 (18)S1—C1—C6—N11.8 (5)
N3i—Ag1—O3—S192.60 (17)C2—C1—C6—C50.8 (5)
N2—Ag1—O3—S196.73 (17)S1—C1—C6—C5174.3 (3)
N1—Ag1—O3—S12.08 (16)C10—N2—C7—C81.6 (5)
N3i—Ag1—N2—C7113.6 (4)Ag1—N2—C7—C8178.8 (2)
N1—Ag1—N2—C7103.3 (2)C6—C1—C2—C30.4 (5)
O3—Ag1—N2—C722.8 (3)S1—C1—C2—C3175.6 (3)
N3i—Ag1—N2—C1069.3 (5)C1—C2—C3—C41.1 (5)
N1—Ag1—N2—C1073.8 (3)C1—C2—C3—Cl1179.1 (3)
O3—Ag1—N2—C10154.3 (3)C2—C3—C4—C50.7 (5)
C7—N2—C10—C90.2 (5)Cl1—C3—C4—C5179.5 (3)
Ag1—N2—C10—C9177.4 (2)C3—C4—C5—C60.5 (6)
C7—N2—C10—C11179.7 (3)N1—C6—C5—C4177.4 (3)
Ag1—N2—C10—C112.6 (4)C1—C6—C5—C41.3 (5)
N3i—Ag1—N1—C640.2 (2)N2—C7—C8—N31.8 (5)
N2—Ag1—N1—C6147.8 (2)N2—C7—C8—C12179.0 (3)
O3—Ag1—N1—C658.1 (2)C7—C8—N3—C90.5 (5)
O2—S1—C1—C2136.8 (3)C12—C8—N3—C9179.7 (3)
O3—S1—C1—C2103.3 (3)C7—C8—N3—Ag1ii166.4 (2)
O1—S1—C1—C216.5 (3)C12—C8—N3—Ag1ii12.8 (4)
O2—S1—C1—C648.0 (3)C8—N3—C9—C100.9 (5)
O3—S1—C1—C671.9 (3)Ag1ii—N3—C9—C10168.5 (3)
O1—S1—C1—C6168.3 (3)N2—C10—C9—N31.1 (5)
Ag1—N1—C6—C5108.1 (3)C11—C10—C9—N3179.0 (4)
Symmetry codes: (i) x+1/2, y1/2, z+1/2; (ii) x+1/2, y+1/2, z1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—HN1···O1iii0.84 (1)2.15 (1)2.968 (3)165 (3)
N1—HN2···O20.84 (1)2.34 (3)2.890 (4)124 (3)
Symmetry code: (iii) x+1/2, y+3/2, z.

Experimental details

Crystal data
Chemical formula[Ag(C6H5ClNO3S)(C6H8N2)]
Mr422.63
Crystal system, space groupOrthorhombic, Pna21
Temperature (K)293
a, b, c (Å)14.671 (3), 11.947 (2), 8.2025 (16)
V3)1437.7 (5)
Z4
Radiation typeMo Kα
µ (mm1)1.75
Crystal size (mm)0.32 × 0.23 × 0.06
Data collection
DiffractometerRigaku R-AXIS RAPID
Absorption correctionMulti-scan
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.653, 0.906
No. of measured, independent and
observed [I > 2σ(I)] reflections
11475, 2935, 2638
Rint0.034
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.025, 0.053, 1.05
No. of reflections2935
No. of parameters200
No. of restraints4
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.37, 0.33
Absolute structureFlack (1983), 1172 Friedel pairs
Absolute structure parameter0.03 (3)

Computer programs: PROCESS-AUTO (Rigaku, 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Sheldrick, 1990).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—HN1···O1i0.841 (10)2.146 (12)2.968 (3)165 (3)
N1—HN2···O20.840 (10)2.34 (3)2.890 (4)124 (3)
Symmetry code: (i) x+1/2, y+3/2, z.
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds