(2-Amino-5-chloro­benzene­sulfonato-κO)bis­(3-methyl­isoquinoline-κN)silver(I)

Qiang Liu; Li Feng; Yu-Jie Li; Xian-Wu Dong

doi:10.1107/S1600536810009220

. 2010 Mar 17;66(Pt 4):m415. doi: 10.1107/S1600536810009220

(2-Amino-5-chlorobenzenesulfonato-κO)bis(3-methylisoquinoline-κN)silver(I)

Qiang Liu ^a, Li Feng ^a, Yu-Jie Li ^a, Xian-Wu Dong ^a,^*

PMCID: PMC2984077 PMID: 21580513

Abstract

The title compound, [Ag(C₆H₅ClNO₃S)(C₁₀H₉N)₂], crystallizes with two independent molecules in the asymmetric unit. The Ag⁺ cation is three-coordinated by one O atom from the 2-amino-5-chlorobenzenesulfonate anion and two N atoms from two different 3-methylisoquinoline ligands in a slightly distorted trigonal-planar geometry. In the crystal, network of intermolecular N—H⋯O hydrogen-bonding interactions generates a chain along [100].

Related literature

For related structures, see: Li et al. (2007 ▶); Mišek et al. (2008 ▶); Wang et al. (2007 ▶); Shimizu et al. (1999 ▶).

Experimental

Crystal data

[Ag(C₆H₅ClNO₃S)(C₁₀H₉N)₂]
M _r = 600.68
Orthorhombic,
a = 21.184 (2) Å
b = 14.7095 (10) Å
c = 15.6602 (10) Å
V = 4879.8 (6) Å³
Z = 8
Mo Kα radiation
μ = 1.06 mm⁻¹
T = 293 K
0.23 × 0.19 × 0.17 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multiscan (SADABS; Sheldrick, 1996 ▶) T _min = 0.779, T _max = 0.831
13070 measured reflections
8349 independent reflections
3592 reflections with I > 2σ(I)
R _int = 0.086

Refinement

R[F ² > 2σ(F ²)] = 0.056
wR(F ²) = 0.124
S = 0.81
8349 reflections
641 parameters
16 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.85 e Å⁻³
Δρ_min = −0.67 e Å⁻³
Absolute structure: Flack (1983 ▶), 3745 Friedel pairs
Flack parameter: −0.06 (4)

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810009220/zq2031sup1.cif

e-66-0m415-sup1.cif^{(31.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810009220/zq2031Isup2.hkl

e-66-0m415-Isup2.hkl^{(400.2KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N6—H6NA⋯O8	0.83	2.35	2.844 (12)	118
N5—H5NA⋯O9	0.84 (3)	2.20 (5)	3.006 (13)	159 (11)
N5—H5NB⋯O5	0.83 (3)	2.48 (6)	2.973 (14)	119 (4)
N6—H6NB⋯O4ⁱ	0.84	2.30	3.126 (13)	168

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Symmetry code: (i) Inline graphic .

Acknowledgments

We thank Jilin Agricultural Science and Technology College for support.

supplementary crystallographic information

Comment

In the crystal structure of the title compound, each Ag⁺ cation is three-coordinated by one O atom from the 2-amino-5-chlorobenzenesulfonate anion and two N atoms from two different 3-methylisoquinoline ligands in a slightly distorted trigonal-planar geometry (Fig. 1). The Ag—O distances of 2.645 (7) Å and 2.630 (9) Å, and the Ag—N distances in the range 2.158 (10) - 2.200 (9) Å are similar to whose within the previous reports (Li et al., 2007; Mišek et al., 2008; Shimizu et al., 1999; Wang et al., 2007). A network of intermolecular N—H···O hydrogen bonding interactions generates an one-dimensional chain (Fig 2).

Experimental

An aqueous solution (10 ml) of 2-amino-5-chlorobenzene-1-sulfonic acid (0.041 g, 0.5 mmol) was addded to solid Ag₂CO₃ (0.069 g, 0.25 mmol) and stirred for several minutes until no further CO₂ was given off; 3-methylisoquinoline (0.0715 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 the title compound were obtained by evaporation of the solution for several days at room temperature.