metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 11| November 2008| Pages m1413-m1414

Bis(ethyl 2-amino-4-thia­zole­acetato-κN)silver(I) nitrate

aDepartment of Chemistry, Shangrao Normal University, Shangrao 334001, People's Republic of China, and bKey Laboratory of Medicinal Chemical Resources and Molecular Engineering, College of Chemistry and Chemical Engineering, Guangxi Normal University, Guilin 541004, People's Republic of China
*Correspondence e-mail: ljzhang@sru.jx.cn, hliang@mailbox.gxnu.edu.cn

(Received 20 September 2008; accepted 9 October 2008; online 18 October 2008)

In the title complex, [Ag(C7H10N2O2S)2]NO3, the AgI cation is bicoordinated in an almost linear configuration by two N-donor atoms of the thia­zole rings of two distinct ethyl 2-amino-4-thia­zoleacetate (EATA) ligands. The dihedral angle between the two thia­zole rings is 49.9°. A weak Ag⋯O (2.729 Å) inter­action between the Ag cation and one of the O atoms from the nitrate anion is observed, and a pseudo-dimer is formed through a weak Ag⋯S (3.490 Å) inter­action between the Ag cation and the S atom of the thia­zole ring of a symmetry-related mol­ecule. In the crystal structure, there are intra- and inter­molecular N—H⋯O hydrogen bonds. The occurrence of inter­molecular N—H⋯O hydrogen bonds results in the formation of two-dimensional sheets parallel to (010), which are further linked into a three-dimensional network through weak C—H⋯O inter­actions.

Related literature

For related literature on the synthesis, see: Zhang et al. (2008[Zhang, L.-J., Shen, X.-C. & Liang, H. (2008). Acta Cryst. E64, m1248.]). For related crystal structures, see: Dong et al. (2005[Dong, X.-W., Wu, H. & Ma, J.-F. (2005). Acta Cryst. E61, m2400-m2401.]); Fun et al. (2008[Fun, H.-K., Jebas, S. R. & Balasubramanian, T. (2008). Acta Cryst. E64, m668-m669.]); Lee & Lee (2007[Lee, H. K. & Lee, S. W. (2007). Bull. Korean Chem. Soc. 28, 421-426.]); Liu et al. (2007[Liu, B.-X., Chen, G.-H. & Zhang, L.-J. (2007). Acta Cryst. E63, m2263-m2264.]); Zhang et al. (2008[Zhang, L.-J., Shen, X.-C. & Liang, H. (2008). Acta Cryst. E64, m1248.]). For related literature, see: Bolos et al. (1999[Bolos, C. A., Fanourgakis, P. V., Christidis, P. C. & Nikolov, G. S. (1999). Polyhedron, 18, 1661-1668.]); Chang et al. (1982[Chang, C. K., Myoung, S. K. & Ward, B. (1982). Chem. Commun. pp. 716-719.]); Garrison & Youngs (2005[Garrison, J. C. & Youngs, W. J. (2005). Chem. Rev. 105, 3978-4008.]); Nomiya et al. (2000[Nomiya, K., Takahashi, S., Noguchi, R., Nemoto, S., Takayama, T. & Oda, M. (2000). Inorg. Chem. 39, 3301-3311.]).

[Scheme 1]

Experimental

Crystal data
  • [Ag(C7H10N2O2S)2]NO3

  • Mr = 542.36

  • Triclinic, [P \overline 1]

  • a = 7.4900 (15) Å

  • b = 12.350 (3) Å

  • c = 13.015 (3) Å

  • α = 109.32 (3)°

  • β = 101.83 (3)°

  • γ = 105.58 (3)°

  • V = 1035.6 (6) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 1.22 mm−1

  • T = 293 (2) K

  • 0.44 × 0.21 × 0.19 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2 and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.616, Tmax = 0.801

  • 11916 measured reflections

  • 3656 independent reflections

  • 3518 reflections with I > 2σ(I)

  • Rint = 0.016

Refinement
  • R[F2 > 2σ(F2)] = 0.020

  • wR(F2) = 0.053

  • S = 1.10

  • 3656 reflections

  • 265 parameters

  • H-atom parameters constrained

  • Δρmax = 0.38 e Å−3

  • Δρmin = −0.30 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N3—H3A⋯O2i 0.86 2.13 2.955 (3) 162
N3—H3B⋯O6 0.86 2.16 3.019 (3) 175
N5—H5A⋯O1ii 0.86 2.04 2.886 (3) 169
N5—H5B⋯O2iii 0.86 2.14 2.972 (3) 161
C1—H1C⋯O3iv 0.96 2.53 3.298 (3) 137
C4—H4A⋯O3 0.97 2.60 3.492 (4) 153
C4—H4B⋯O2iii 0.97 2.43 3.330 (3) 155
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x+2, -y, -z+2; (iii) x+1, y, z; (iv) -x+2, -y+1, -z+2.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEPIII (Burnett & Johnson, 1996[Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.]), ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and CAMERON (Pearce et al., 2000[Pearce, L., Prout, C. K. & Watkin, D. J. (2000). CAMERON. Chemical Crystallography Laboratory, University of Oxford, England.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

As a further extension of previous works on the synthesis of metal–organic complex containing pharmaceutical intermediates as ligands, here ethyl 2-amino-4-thiazoleacetate (EATA) is again applied as the ligand to obtain coordination complex with potential higher pharmacological activity (Bolos et al., 1999; Chang et al., 1982). Silver cation is chosen as central ion because many silver complexes show excellent antimicrobial effect (Garrison et al., 2005; Nomiya et al., 2000). Moreover, EATA has many conventional coordination atoms such N, O, S and many hydrogen atoms attached to N atoms, which may be in favor of the formation of diverse structures. In a recently similar research, we used cadmium chloride hydrate and 2-amino-4-thiazole acetic acid (ATAA) as starting materials to form a mononuclear compound, dichloridobis(2-amino-5-methyl-1,3-thiazole-κN)cadmium(II), due to the decarboxylization of ATAA under ethanol–water mixed-solvothermal reaction condition (Zhang et al., 2008). To avoid potential instability of EATA under solvothermal condition, we carry out the reaction at low temperature as descried in experimental section and obtain an Ag-EATA complex as expected.

In the title complex, [Ag(C7H10N2O2S)2]NO3, the AgI cation is bicoordinated in an almost linear configuration by two N-donor atoms of thiazole rings of two distinct EATA ligand molecules (Fig. 1). Similar structures have been reported (Dong et al., 2005; Fun et al., 2008; Lee & Lee, 2007; Liu et al., 2007). The N—Ag—N angle and dihedral angle between the two thiazole rings are respectively 175.88 (6) and 49.9°, and the average Ag—N distance is 2.138 (2) Å. In addition, there is a weak Ag···O interaction between silver cation and one of oxygen atoms from a nitrate group (Ag···O = 2.729 Å), while a pseudo dimer is built up through weak Ag···S [3.490 Å (Lee & Lee, 2007)] interaction between silver cation and one sulfur atom on a thiazole ring of a symmetry related molecule (Fig. 2). Thus, the title compound might also be regarded as a four-coordinated Ag complex with a N2OS donor set. In the crystal structure, due to Ag···O, Ag···S weak interactions and intermolecular N—H···O hydrogen bonds between adjacent molecules containing nitrate anions (Table 1), the molecules are extended to form two-dimensional layers (Fig. 2) parallel to the (010) plane, which are further linked to a three dimensional network through weak C—H···O interactions (Table 1).

Related literature top

For related literature on the synthesis, see: Zhang et al. (2008). For related crystal structures, see: Dong et al. (2005); Fun et al. (2008); Lee & Lee (2007); Liu et al. (2007); Zhang et al. (2008). For related literature, see: Bolos et al. (1999); Chang et al. (1982); Garrison et al. (2005); Nomiya et al. (2000).

Experimental top

To 10 ml ethanol solution containing ethyl 2-amino-4-thiazoleacetate (EATA) (0.186 g, 1 mmol), AgNO3 (0.170 g, 1 mmol) was added and the resulting mixture was stirred in the dark at room temperature for 4 h. After the filtrate had been allowed to stand overnight at a refrigerator temperature of 4 °C, the colourless block single crystals suitable for X-ray diffraction were obtained. Yield: 45.3% (based on Ag).

Refinement top

All H atoms attached to C or N atoms were placed in geometrically (C—H = 0.93–0.97 Å, N—H = 0.86 Å) and refined using a riding model, with Uiso(H) = 1.2 or 1.5 Ueq(C) and Uiso(H) = 1.2 Ueq(N).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: APEX2 (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Pearce et al., 2000); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A view of complex (1), with the atom-labeling scheme. Displacement ellipsoids are drawn at the 30% probability level. H bond and weak Ag···O interactions are shown as dashed lines. Only H atoms involved in hydrogen bondings are shown. H atoms are drawn as small spheres of arbitrary radii.
[Figure 2] Fig. 2. Partial packing view of (I), showing the formation of the pseudo dimer through weak Ag···S interactions and the two-dimensional network structure via intermolecular N—H···O hydrogen bonds. The weak interactions are represented as dashed lines. Hydrogen atoms not involved in hydrogen bonds were omitted for clarity.
Bis(ethyl 2-amino-4-thiazoleacetato-κN)silver(I) nitrate top
Crystal data top
[Ag(C7H10N2O2S)2]NO3Z = 2
Mr = 542.36F(000) = 548
Triclinic, P1Dx = 1.739 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.4900 (15) ÅCell parameters from 3656 reflections
b = 12.350 (3) Åθ = 1.8–25.1°
c = 13.015 (3) ŵ = 1.22 mm1
α = 109.32 (3)°T = 293 K
β = 101.83 (3)°Block, colourless
γ = 105.58 (3)°0.44 × 0.21 × 0.19 mm
V = 1035.6 (6) Å3
Data collection top
Bruker APEXII CCD area-detector
diffractometer
3656 independent reflections
Radiation source: fine-focus sealed tube3518 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.016
ϕ and ω scansθmax = 25.1°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
h = 88
Tmin = 0.616, Tmax = 0.801k = 1414
11916 measured reflectionsl = 1515
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)] = 0.020H-atom parameters constrained
wR(F2) = 0.053 w = 1/[σ2(Fo2) + (0.0247P)2 + 0.5391P]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max = 0.001
3656 reflectionsΔρmax = 0.38 e Å3
265 parametersΔρmin = 0.30 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 constraintsExtinction coefficient: 0.0267 (10)
Primary atom site location: structure-invariant direct methods
Crystal data top
[Ag(C7H10N2O2S)2]NO3γ = 105.58 (3)°
Mr = 542.36V = 1035.6 (6) Å3
Triclinic, P1Z = 2
a = 7.4900 (15) ÅMo Kα radiation
b = 12.350 (3) ŵ = 1.22 mm1
c = 13.015 (3) ÅT = 293 K
α = 109.32 (3)°0.44 × 0.21 × 0.19 mm
β = 101.83 (3)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer
3656 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
3518 reflections with I > 2σ(I)
Tmin = 0.616, Tmax = 0.801Rint = 0.016
11916 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0200 restraints
wR(F2) = 0.053H-atom parameters constrained
S = 1.10Δρmax = 0.38 e Å3
3656 reflectionsΔρmin = 0.30 e Å3
265 parameters
Special details top

Experimental. FT–IR (KBr, cm-1):3409 vs, 3296 ms, 3206 ms, 3152 s, 2987 m, 2942 w, 2906 w, 2733 w, 2346 w, 1740 vs, 1706 vs, 1627 vs, 1565 m, 1541 vs, 1526 ms, 1477 m, 1448 m, 1402 ms, 1384 vs, 1321 s, 1249 ms, 1174 vs, 1131 ms, 1115 ms, 1029 ms, 995 w, 980 m, 948 w, 826 w, 752 w, 717 m, 658 w, 596 w, 547 w.

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
Ag10.85033 (2)0.013259 (13)0.716062 (13)0.04021 (8)
S10.91350 (9)0.16283 (5)0.45565 (5)0.04745 (15)
S20.90581 (10)0.23263 (6)0.94281 (5)0.05325 (16)
O60.5425 (3)0.22530 (17)0.55153 (16)0.0687 (5)
O70.3231 (2)0.39127 (14)0.54375 (13)0.0474 (4)
O51.2202 (3)0.48839 (16)0.81321 (16)0.0736 (6)
O41.2230 (3)0.45176 (13)0.96884 (13)0.0515 (4)
N30.6973 (3)0.05628 (17)0.44144 (16)0.0516 (5)
H3B0.65550.10770.47020.062*
H3A0.65740.07820.36820.062*
N20.8931 (2)0.09958 (15)0.62234 (14)0.0345 (3)
N51.1602 (3)0.06100 (19)0.90954 (18)0.0560 (5)
H5B1.19240.01010.87870.067*
H5A1.24910.06740.95830.067*
N40.8272 (2)0.12730 (14)0.80909 (14)0.0344 (3)
C80.9742 (3)0.12943 (18)0.88205 (17)0.0374 (4)
C90.6656 (4)0.2735 (2)0.8643 (2)0.0510 (6)
H90.56010.33220.86630.061*
C100.6507 (3)0.20965 (18)0.79984 (17)0.0390 (5)
C110.4644 (3)0.2204 (2)0.7219 (2)0.0510 (6)
H11B0.45720.13920.74040.061*
H11A0.35440.27080.73460.061*
C120.4492 (3)0.2767 (2)0.59729 (19)0.0445 (5)
C130.2915 (4)0.4515 (2)0.42144 (19)0.0558 (6)
H13B0.41160.45920.40890.067*
H13A0.25050.40370.38200.067*
C70.8230 (3)0.05670 (19)0.50993 (17)0.0368 (4)
C61.0455 (4)0.2706 (2)0.59426 (19)0.0453 (5)
H61.12540.35110.61340.054*
C51.0172 (3)0.22243 (18)0.67040 (17)0.0360 (4)
C41.0999 (3)0.27987 (18)0.79796 (18)0.0428 (5)
H4B1.20090.24880.82000.051*
H4A0.99690.25150.82800.051*
C31.1861 (3)0.41749 (19)0.85648 (19)0.0420 (5)
C21.2986 (4)0.5826 (2)1.0409 (2)0.0542 (6)
H2B1.20730.62001.01870.065*
H2A1.42290.62281.03350.065*
C11.3247 (4)0.5950 (2)1.1613 (2)0.0621 (7)
H1C1.36630.68041.21170.093*
H1B1.42200.56271.18380.093*
H1A1.20270.55001.16610.093*
C140.1377 (5)0.5744 (3)0.3773 (3)0.0772 (9)
H14C0.02170.56590.39370.116*
H14B0.18280.62260.41380.116*
H14A0.10850.61490.29570.116*
O30.6428 (4)0.1229 (2)0.8055 (2)0.0928 (8)
O20.3485 (3)0.09345 (19)0.80013 (16)0.0650 (5)
O10.5549 (3)0.1152 (2)0.9498 (2)0.0903 (7)
N10.5176 (3)0.10894 (16)0.85172 (17)0.0447 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ag10.04525 (12)0.03583 (10)0.03859 (11)0.00714 (7)0.00920 (7)0.02277 (7)
S10.0633 (4)0.0491 (3)0.0388 (3)0.0198 (3)0.0174 (3)0.0284 (2)
S20.0699 (4)0.0490 (3)0.0467 (3)0.0141 (3)0.0173 (3)0.0335 (3)
O60.0612 (11)0.0628 (11)0.0586 (11)0.0110 (9)0.0136 (9)0.0270 (9)
O70.0490 (9)0.0414 (8)0.0380 (8)0.0015 (7)0.0134 (7)0.0123 (6)
O50.1150 (17)0.0405 (9)0.0550 (10)0.0061 (10)0.0262 (11)0.0260 (8)
O40.0712 (11)0.0317 (7)0.0418 (8)0.0070 (7)0.0152 (8)0.0144 (6)
N30.0577 (12)0.0486 (11)0.0350 (9)0.0045 (9)0.0063 (8)0.0182 (8)
N20.0366 (9)0.0355 (8)0.0344 (8)0.0114 (7)0.0120 (7)0.0189 (7)
N50.0381 (10)0.0671 (13)0.0624 (13)0.0072 (9)0.0044 (9)0.0426 (11)
N40.0361 (9)0.0317 (8)0.0326 (8)0.0062 (7)0.0098 (7)0.0157 (7)
C80.0441 (11)0.0355 (10)0.0329 (10)0.0092 (9)0.0120 (8)0.0187 (8)
C90.0569 (14)0.0420 (12)0.0480 (13)0.0014 (10)0.0224 (11)0.0210 (10)
C100.0403 (11)0.0323 (10)0.0351 (10)0.0033 (8)0.0144 (8)0.0093 (8)
C110.0375 (12)0.0499 (13)0.0487 (13)0.0064 (10)0.0122 (10)0.0086 (10)
C120.0336 (11)0.0438 (11)0.0466 (12)0.0054 (9)0.0075 (9)0.0176 (10)
C130.0608 (15)0.0563 (14)0.0383 (12)0.0090 (12)0.0167 (11)0.0147 (11)
C70.0384 (10)0.0431 (11)0.0361 (10)0.0169 (9)0.0134 (8)0.0222 (9)
C60.0579 (13)0.0384 (11)0.0436 (12)0.0133 (10)0.0185 (10)0.0236 (9)
C50.0397 (11)0.0347 (10)0.0397 (11)0.0137 (8)0.0150 (9)0.0209 (8)
C40.0528 (13)0.0345 (10)0.0387 (11)0.0094 (9)0.0119 (9)0.0191 (9)
C30.0427 (11)0.0375 (11)0.0455 (12)0.0098 (9)0.0148 (9)0.0202 (9)
C20.0675 (16)0.0313 (11)0.0519 (13)0.0083 (10)0.0149 (12)0.0133 (10)
C10.0799 (19)0.0441 (13)0.0509 (14)0.0155 (12)0.0170 (13)0.0141 (11)
C140.082 (2)0.0566 (16)0.0553 (16)0.0010 (14)0.0250 (15)0.0027 (13)
O30.0874 (16)0.0820 (15)0.147 (2)0.0438 (13)0.0819 (16)0.0554 (15)
O20.0496 (10)0.0931 (14)0.0609 (11)0.0222 (9)0.0117 (8)0.0483 (10)
O10.0676 (13)0.1224 (19)0.0748 (14)0.0182 (13)0.0027 (11)0.0614 (14)
N10.0436 (10)0.0380 (9)0.0576 (12)0.0144 (8)0.0184 (9)0.0250 (8)
Geometric parameters (Å, º) top
Ag1—N42.1361 (17)C11—C121.504 (3)
Ag1—N22.1396 (17)C11—H11B0.9700
S1—C61.725 (3)C11—H11A0.9700
S1—C71.734 (2)C13—C141.474 (4)
S2—C91.719 (3)C13—H13B0.9700
S2—C81.730 (2)C13—H13A0.9700
O6—C121.195 (3)C6—C51.338 (3)
O7—C121.319 (3)C6—H60.9300
O7—C131.453 (3)C5—C41.485 (3)
O5—C31.189 (3)C4—C31.496 (3)
O4—C31.325 (3)C4—H4B0.9700
O4—C21.449 (3)C4—H4A0.9700
N3—C71.325 (3)C2—C11.489 (3)
N3—H3B0.8600C2—H2B0.9700
N3—H3A0.8600C2—H2A0.9700
N2—C71.311 (3)C1—H1C0.9600
N2—C51.390 (3)C1—H1B0.9600
N5—C81.321 (3)C1—H1A0.9600
N5—H5B0.8600C14—H14C0.9600
N5—H5A0.8600C14—H14B0.9600
N4—C81.311 (3)C14—H14A0.9600
N4—C101.389 (3)O3—N11.218 (3)
C9—C101.336 (3)O2—N11.236 (3)
C9—H90.9300O1—N11.221 (3)
C10—C111.491 (3)
N4—Ag1—N2175.88 (6)H13B—C13—H13A108.5
C6—S1—C789.44 (10)N2—C7—N3125.01 (19)
C9—S2—C889.17 (11)N2—C7—S1113.38 (16)
C12—O7—C13116.29 (18)N3—C7—S1121.60 (16)
C3—O4—C2117.66 (18)C5—C6—S1110.73 (17)
C7—N3—H3B120.0C5—C6—H6124.6
C7—N3—H3A120.0S1—C6—H6124.6
H3B—N3—H3A120.0C6—C5—N2114.81 (19)
C7—N2—C5111.58 (17)C6—C5—C4129.80 (19)
C7—N2—Ag1123.44 (14)N2—C5—C4115.38 (17)
C5—N2—Ag1124.52 (13)C5—C4—C3117.78 (18)
C8—N5—H5B120.0C5—C4—H4B107.9
C8—N5—H5A120.0C3—C4—H4B107.9
H5B—N5—H5A120.0C5—C4—H4A107.9
C8—N4—C10110.89 (17)C3—C4—H4A107.9
C8—N4—Ag1125.47 (13)H4B—C4—H4A107.2
C10—N4—Ag1123.65 (14)O5—C3—O4123.3 (2)
N4—C8—N5125.14 (19)O5—C3—C4127.6 (2)
N4—C8—S2113.98 (15)O4—C3—C4109.03 (18)
N5—C8—S2120.88 (17)O4—C2—C1106.58 (19)
C10—C9—S2110.93 (17)O4—C2—H2B110.4
C10—C9—H9124.5C1—C2—H2B110.4
S2—C9—H9124.5O4—C2—H2A110.4
C9—C10—N4115.0 (2)C1—C2—H2A110.4
C9—C10—C11125.5 (2)H2B—C2—H2A108.6
N4—C10—C11119.43 (19)C2—C1—H1C109.5
C10—C11—C12112.00 (19)C2—C1—H1B109.5
C10—C11—H11B109.2H1C—C1—H1B109.5
C12—C11—H11B109.2C2—C1—H1A109.5
C10—C11—H11A109.2H1C—C1—H1A109.5
C12—C11—H11A109.2H1B—C1—H1A109.5
H11B—C11—H11A107.9C13—C14—H14C109.5
O6—C12—O7123.2 (2)C13—C14—H14B109.5
O6—C12—C11124.5 (2)H14C—C14—H14B109.5
O7—C12—C11112.28 (19)C13—C14—H14A109.5
O7—C13—C14107.5 (2)H14C—C14—H14A109.5
O7—C13—H13B110.2H14B—C14—H14A109.5
C14—C13—H13B110.2O3—N1—O1122.3 (2)
O7—C13—H13A110.2O3—N1—O2119.3 (2)
C14—C13—H13A110.2O1—N1—O2118.4 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···O2i0.862.132.955 (3)162
N3—H3B···O60.862.163.019 (3)175
N5—H5A···O1ii0.862.042.886 (3)169
N5—H5B···O2iii0.862.142.972 (3)161
C1—H1C···O3iv0.962.533.298 (3)137
C4—H4A···O30.972.603.492 (4)153
C4—H4B···O2iii0.972.433.330 (3)155
Symmetry codes: (i) x+1, y, z+1; (ii) x+2, y, z+2; (iii) x+1, y, z; (iv) x+2, y+1, z+2.

Experimental details

Crystal data
Chemical formula[Ag(C7H10N2O2S)2]NO3
Mr542.36
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)7.4900 (15), 12.350 (3), 13.015 (3)
α, β, γ (°)109.32 (3), 101.83 (3), 105.58 (3)
V3)1035.6 (6)
Z2
Radiation typeMo Kα
µ (mm1)1.22
Crystal size (mm)0.44 × 0.21 × 0.19
Data collection
DiffractometerBruker APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2004)
Tmin, Tmax0.616, 0.801
No. of measured, independent and
observed [I > 2σ(I)] reflections
11916, 3656, 3518
Rint0.016
(sin θ/λ)max1)0.597
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.020, 0.053, 1.10
No. of reflections3656
No. of parameters265
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.38, 0.30

Computer programs: APEX2 (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Pearce et al., 2000).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···O2i0.862.132.955 (3)161.6
N3—H3B···O60.862.163.019 (3)175.1
N5—H5A···O1ii0.862.042.886 (3)169.1
N5—H5B···O2iii0.862.142.972 (3)161.1
C1—H1C···O3iv0.962.533.298 (3)137.3
C4—H4A···O30.972.603.492 (4)153.1
C4—H4B···O2iii0.972.433.330 (3)154.5
Symmetry codes: (i) x+1, y, z+1; (ii) x+2, y, z+2; (iii) x+1, y, z; (iv) x+2, y+1, z+2.
 

Acknowledgements

The authors thank Dr S.-H. Zhang for helpful discussions. The authors also acknowledge financial support from the National Natural Science Foundation of China (grant No. 20701010), the Natural Science Foundation of Guangxi Province (grant No. 0728094) and Jiangxi Provincial Department of Education [grant No. (2007)348].

References

First citationBolos, C. A., Fanourgakis, P. V., Christidis, P. C. & Nikolov, G. S. (1999). Polyhedron, 18, 1661–1668.  Web of Science CSD CrossRef CAS Google Scholar
First citationBruker (2004). APEX2 and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationBurnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.  Google Scholar
First citationChang, C. K., Myoung, S. K. & Ward, B. (1982). Chem. Commun. pp. 716–719.  CrossRef Google Scholar
First citationDong, X.-W., Wu, H. & Ma, J.-F. (2005). Acta Cryst. E61, m2400–m2401.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationFun, H.-K., Jebas, S. R. & Balasubramanian, T. (2008). Acta Cryst. E64, m668–m669.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationGarrison, J. C. & Youngs, W. J. (2005). Chem. Rev. 105, 3978–4008.  Web of Science CrossRef PubMed CAS Google Scholar
First citationLee, H. K. & Lee, S. W. (2007). Bull. Korean Chem. Soc. 28, 421–426.  CAS Google Scholar
First citationLiu, B.-X., Chen, G.-H. & Zhang, L.-J. (2007). Acta Cryst. E63, m2263–m2264.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationNomiya, K., Takahashi, S., Noguchi, R., Nemoto, S., Takayama, T. & Oda, M. (2000). Inorg. Chem. 39, 3301–3311.  Web of Science CSD CrossRef PubMed CAS Google Scholar
First citationPearce, L., Prout, C. K. & Watkin, D. J. (2000). CAMERON. Chemical Crystallography Laboratory, University of Oxford, England.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationZhang, L.-J., Shen, X.-C. & Liang, H. (2008). Acta Cryst. E64, m1248.  Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 11| November 2008| Pages m1413-m1414
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds