Bis(ethyl 2-amino-4-thia-zoleacetato-κN)silver(I) nitrate.

In the title complex, [Ag(C(7)H(10)N(2)O(2)S)(2)]NO(3), the Ag(I) cation is bicoordinated in an almost linear configuration by two N-donor atoms of the thia-zole rings of two distinct ethyl 2-amino-4-thia-zoleacetate (EATA) ligands. The dihedral angle between the two thia-zole rings is 49.9°. A weak Ag⋯O (2.729 Å) inter-action 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) inter-action between the Ag cation and the S atom of the thia-zole ring of a symmetry-related mol-ecule. In the crystal structure, there are intra- and inter-molecular N-H⋯O hydrogen bonds. The occurrence of inter-molecular 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 inter-actions.

Related literature

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 & Youngs (2005 ▶); Nomiya et al. (2000 ▶).

Experimental

Crystal data

[Ag(C7H10N2O2S)2]NO3

M = 542.36

Triclinic,

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 ▶) T min = 0.616, T max = 0.801

11916 measured reflections

3656 independent reflections

3518 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.020

wR(F 2) = 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

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2; data reduction: APEX2; 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808032686/dn2382sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808032686/dn2382Isup2.hkl

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

[Ag(C7H10N2O2S)2]NO3	Z = 2
Mr = 542.36	F(000) = 548
Triclinic, P1	Dx = 1.739 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4900 (15) Å	Cell parameters from 3656 reflections
b = 12.350 (3) Å	θ = 1.8–25.1°
c = 13.015 (3) Å	µ = 1.22 mm−1
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

Bruker APEXII CCD area-detector diffractometer	3656 independent reflections
Radiation source: fine-focus sealed tube	3518 reflections with I > 2σ(I)
graphite	Rint = 0.016
φ and ω scans	θmax = 25.1°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −8→8
Tmin = 0.616, Tmax = 0.801	k = −14→14
11916 measured reflections	l = −15→15

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)] = 0.020	H-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 reflections	Δρmax = 0.38 e Å−3
265 parameters	Δρmin = −0.30 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 constraints	Extinction coefficient: 0.0267 (10)
Primary atom site location: structure-invariant direct methods

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.

	x	y	z	Uiso*/Ueq
Ag1	0.85033 (2)	−0.013259 (13)	0.716062 (13)	0.04021 (8)
S1	0.91350 (9)	0.16283 (5)	0.45565 (5)	0.04745 (15)
S2	0.90581 (10)	−0.23263 (6)	0.94281 (5)	0.05325 (16)
O6	0.5425 (3)	−0.22530 (17)	0.55153 (16)	0.0687 (5)
O7	0.3231 (2)	−0.39127 (14)	0.54375 (13)	0.0474 (4)
O5	1.2202 (3)	0.48839 (16)	0.81321 (16)	0.0736 (6)
O4	1.2230 (3)	0.45176 (13)	0.96884 (13)	0.0515 (4)
N3	0.6973 (3)	−0.05628 (17)	0.44144 (16)	0.0516 (5)
H3B	0.6555	−0.1077	0.4702	0.062*
H3A	0.6574	−0.0782	0.3682	0.062*
N2	0.8931 (2)	0.09958 (15)	0.62234 (14)	0.0345 (3)
N5	1.1602 (3)	−0.06100 (19)	0.90954 (18)	0.0560 (5)
H5B	1.1924	−0.0101	0.8787	0.067*
H5A	1.2491	−0.0674	0.9583	0.067*
N4	0.8272 (2)	−0.12730 (14)	0.80909 (14)	0.0344 (3)
C8	0.9742 (3)	−0.12943 (18)	0.88205 (17)	0.0374 (4)
C9	0.6656 (4)	−0.2735 (2)	0.8643 (2)	0.0510 (6)
H9	0.5601	−0.3322	0.8663	0.061*
C10	0.6507 (3)	−0.20965 (18)	0.79984 (17)	0.0390 (5)
C11	0.4644 (3)	−0.2204 (2)	0.7219 (2)	0.0510 (6)
H11B	0.4572	−0.1392	0.7404	0.061*
H11A	0.3544	−0.2708	0.7346	0.061*
C12	0.4492 (3)	−0.2767 (2)	0.59729 (19)	0.0445 (5)
C13	0.2915 (4)	−0.4515 (2)	0.42144 (19)	0.0558 (6)
H13B	0.4116	−0.4592	0.4089	0.067*
H13A	0.2505	−0.4037	0.3820	0.067*
C7	0.8230 (3)	0.05670 (19)	0.50993 (17)	0.0368 (4)
C6	1.0455 (4)	0.2706 (2)	0.59426 (19)	0.0453 (5)
H6	1.1254	0.3511	0.6134	0.054*
C5	1.0172 (3)	0.22243 (18)	0.67040 (17)	0.0360 (4)
C4	1.0999 (3)	0.27987 (18)	0.79796 (18)	0.0428 (5)
H4B	1.2009	0.2488	0.8200	0.051*
H4A	0.9969	0.2515	0.8280	0.051*
C3	1.1861 (3)	0.41749 (19)	0.85648 (19)	0.0420 (5)
C2	1.2986 (4)	0.5826 (2)	1.0409 (2)	0.0542 (6)
H2B	1.2073	0.6200	1.0187	0.065*
H2A	1.4229	0.6228	1.0335	0.065*
C1	1.3247 (4)	0.5950 (2)	1.1613 (2)	0.0621 (7)
H1C	1.3663	0.6804	1.2117	0.093*
H1B	1.4220	0.5627	1.1838	0.093*
H1A	1.2027	0.5500	1.1661	0.093*
C14	0.1377 (5)	−0.5744 (3)	0.3773 (3)	0.0772 (9)
H14C	0.0217	−0.5659	0.3937	0.116*
H14B	0.1828	−0.6226	0.4138	0.116*
H14A	0.1085	−0.6149	0.2957	0.116*
O3	0.6428 (4)	0.1229 (2)	0.8055 (2)	0.0928 (8)
O2	0.3485 (3)	0.09345 (19)	0.80013 (16)	0.0650 (5)
O1	0.5549 (3)	0.1152 (2)	0.9498 (2)	0.0903 (7)
N1	0.5176 (3)	0.10894 (16)	0.85172 (17)	0.0447 (4)

	U11	U22	U33	U12	U13	U23
Ag1	0.04525 (12)	0.03583 (10)	0.03859 (11)	0.00714 (7)	0.00920 (7)	0.02277 (7)
S1	0.0633 (4)	0.0491 (3)	0.0388 (3)	0.0198 (3)	0.0174 (3)	0.0284 (2)
S2	0.0699 (4)	0.0490 (3)	0.0467 (3)	0.0141 (3)	0.0173 (3)	0.0335 (3)
O6	0.0612 (11)	0.0628 (11)	0.0586 (11)	−0.0110 (9)	0.0136 (9)	0.0270 (9)
O7	0.0490 (9)	0.0414 (8)	0.0380 (8)	0.0015 (7)	0.0134 (7)	0.0123 (6)
O5	0.1150 (17)	0.0405 (9)	0.0550 (10)	0.0061 (10)	0.0262 (11)	0.0260 (8)
O4	0.0712 (11)	0.0317 (7)	0.0418 (8)	0.0070 (7)	0.0152 (8)	0.0144 (6)
N3	0.0577 (12)	0.0486 (11)	0.0350 (9)	0.0045 (9)	0.0063 (8)	0.0182 (8)
N2	0.0366 (9)	0.0355 (8)	0.0344 (8)	0.0114 (7)	0.0120 (7)	0.0189 (7)
N5	0.0381 (10)	0.0671 (13)	0.0624 (13)	0.0072 (9)	0.0044 (9)	0.0426 (11)
N4	0.0361 (9)	0.0317 (8)	0.0326 (8)	0.0062 (7)	0.0098 (7)	0.0157 (7)
C8	0.0441 (11)	0.0355 (10)	0.0329 (10)	0.0092 (9)	0.0120 (8)	0.0187 (8)
C9	0.0569 (14)	0.0420 (12)	0.0480 (13)	0.0014 (10)	0.0224 (11)	0.0210 (10)
C10	0.0403 (11)	0.0323 (10)	0.0351 (10)	0.0033 (8)	0.0144 (8)	0.0093 (8)
C11	0.0375 (12)	0.0499 (13)	0.0487 (13)	0.0064 (10)	0.0122 (10)	0.0086 (10)
C12	0.0336 (11)	0.0438 (11)	0.0466 (12)	0.0054 (9)	0.0075 (9)	0.0176 (10)
C13	0.0608 (15)	0.0563 (14)	0.0383 (12)	0.0090 (12)	0.0167 (11)	0.0147 (11)
C7	0.0384 (10)	0.0431 (11)	0.0361 (10)	0.0169 (9)	0.0134 (8)	0.0222 (9)
C6	0.0579 (13)	0.0384 (11)	0.0436 (12)	0.0133 (10)	0.0185 (10)	0.0236 (9)
C5	0.0397 (11)	0.0347 (10)	0.0397 (11)	0.0137 (8)	0.0150 (9)	0.0209 (8)
C4	0.0528 (13)	0.0345 (10)	0.0387 (11)	0.0094 (9)	0.0119 (9)	0.0191 (9)
C3	0.0427 (11)	0.0375 (11)	0.0455 (12)	0.0098 (9)	0.0148 (9)	0.0202 (9)
C2	0.0675 (16)	0.0313 (11)	0.0519 (13)	0.0083 (10)	0.0149 (12)	0.0133 (10)
C1	0.0799 (19)	0.0441 (13)	0.0509 (14)	0.0155 (12)	0.0170 (13)	0.0141 (11)
C14	0.082 (2)	0.0566 (16)	0.0553 (16)	−0.0010 (14)	0.0250 (15)	−0.0027 (13)
O3	0.0874 (16)	0.0820 (15)	0.147 (2)	0.0438 (13)	0.0819 (16)	0.0554 (15)
O2	0.0496 (10)	0.0931 (14)	0.0609 (11)	0.0222 (9)	0.0117 (8)	0.0483 (10)
O1	0.0676 (13)	0.1224 (19)	0.0748 (14)	0.0182 (13)	−0.0027 (11)	0.0614 (14)
N1	0.0436 (10)	0.0380 (9)	0.0576 (12)	0.0144 (8)	0.0184 (9)	0.0250 (8)

Ag1—N4	2.1361 (17)	C11—C12	1.504 (3)
Ag1—N2	2.1396 (17)	C11—H11B	0.9700
S1—C6	1.725 (3)	C11—H11A	0.9700
S1—C7	1.734 (2)	C13—C14	1.474 (4)
S2—C9	1.719 (3)	C13—H13B	0.9700
S2—C8	1.730 (2)	C13—H13A	0.9700
O6—C12	1.195 (3)	C6—C5	1.338 (3)
O7—C12	1.319 (3)	C6—H6	0.9300
O7—C13	1.453 (3)	C5—C4	1.485 (3)
O5—C3	1.189 (3)	C4—C3	1.496 (3)
O4—C3	1.325 (3)	C4—H4B	0.9700
O4—C2	1.449 (3)	C4—H4A	0.9700
N3—C7	1.325 (3)	C2—C1	1.489 (3)
N3—H3B	0.8600	C2—H2B	0.9700
N3—H3A	0.8600	C2—H2A	0.9700
N2—C7	1.311 (3)	C1—H1C	0.9600
N2—C5	1.390 (3)	C1—H1B	0.9600
N5—C8	1.321 (3)	C1—H1A	0.9600
N5—H5B	0.8600	C14—H14C	0.9600
N5—H5A	0.8600	C14—H14B	0.9600
N4—C8	1.311 (3)	C14—H14A	0.9600
N4—C10	1.389 (3)	O3—N1	1.218 (3)
C9—C10	1.336 (3)	O2—N1	1.236 (3)
C9—H9	0.9300	O1—N1	1.221 (3)
C10—C11	1.491 (3)
N4—Ag1—N2	175.88 (6)	H13B—C13—H13A	108.5
C6—S1—C7	89.44 (10)	N2—C7—N3	125.01 (19)
C9—S2—C8	89.17 (11)	N2—C7—S1	113.38 (16)
C12—O7—C13	116.29 (18)	N3—C7—S1	121.60 (16)
C3—O4—C2	117.66 (18)	C5—C6—S1	110.73 (17)
C7—N3—H3B	120.0	C5—C6—H6	124.6
C7—N3—H3A	120.0	S1—C6—H6	124.6
H3B—N3—H3A	120.0	C6—C5—N2	114.81 (19)
C7—N2—C5	111.58 (17)	C6—C5—C4	129.80 (19)
C7—N2—Ag1	123.44 (14)	N2—C5—C4	115.38 (17)
C5—N2—Ag1	124.52 (13)	C5—C4—C3	117.78 (18)
C8—N5—H5B	120.0	C5—C4—H4B	107.9
C8—N5—H5A	120.0	C3—C4—H4B	107.9
H5B—N5—H5A	120.0	C5—C4—H4A	107.9
C8—N4—C10	110.89 (17)	C3—C4—H4A	107.9
C8—N4—Ag1	125.47 (13)	H4B—C4—H4A	107.2
C10—N4—Ag1	123.65 (14)	O5—C3—O4	123.3 (2)
N4—C8—N5	125.14 (19)	O5—C3—C4	127.6 (2)
N4—C8—S2	113.98 (15)	O4—C3—C4	109.03 (18)
N5—C8—S2	120.88 (17)	O4—C2—C1	106.58 (19)
C10—C9—S2	110.93 (17)	O4—C2—H2B	110.4
C10—C9—H9	124.5	C1—C2—H2B	110.4
S2—C9—H9	124.5	O4—C2—H2A	110.4
C9—C10—N4	115.0 (2)	C1—C2—H2A	110.4
C9—C10—C11	125.5 (2)	H2B—C2—H2A	108.6
N4—C10—C11	119.43 (19)	C2—C1—H1C	109.5
C10—C11—C12	112.00 (19)	C2—C1—H1B	109.5
C10—C11—H11B	109.2	H1C—C1—H1B	109.5
C12—C11—H11B	109.2	C2—C1—H1A	109.5
C10—C11—H11A	109.2	H1C—C1—H1A	109.5
C12—C11—H11A	109.2	H1B—C1—H1A	109.5
H11B—C11—H11A	107.9	C13—C14—H14C	109.5
O6—C12—O7	123.2 (2)	C13—C14—H14B	109.5
O6—C12—C11	124.5 (2)	H14C—C14—H14B	109.5
O7—C12—C11	112.28 (19)	C13—C14—H14A	109.5
O7—C13—C14	107.5 (2)	H14C—C14—H14A	109.5
O7—C13—H13B	110.2	H14B—C14—H14A	109.5
C14—C13—H13B	110.2	O3—N1—O1	122.3 (2)
O7—C13—H13A	110.2	O3—N1—O2	119.3 (2)
C14—C13—H13A	110.2	O1—N1—O2	118.4 (2)

D—H···A	D—H	H···A	D···A	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

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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) ; (ii) ; (iii) ; (iv) .