Poly[[(μ(2)-2-amino-4,5-dimethybenzene-sulfonato-κN:O)(μ(2)-2-methyl-pyrazine-κN:N')silver(I)] monohydrate].

In the title compound, {[Ag(C(8)H(10)NO(3)S)(C(7)H(6)N(2))]·H(2)O}(n), each Ag(I) cation is four-coordinated by three N atoms from two different 2-methyl-pyrazine ligands and one -NH(2) group of a 2-amino-4,5-dimethybenzene-sulfonate ligand, and by one sulfonate O atom, in a distorted tetra-hedral coordination geometry. The Ag(I) centres are bridged by both types of ligands, forming a two-dimensional network. N-H⋯O hydrogen bonds and O⋯O inter-actions complete the structure.

Related literature

For related literature, see: Cote & Shimizu (2004 ▶); Li et al. (2005 ▶); Liu et al. (2007 ▶).

Experimental

Crystal data

[Ag(C8H10NO3S)(C7H6N2)]·H2O

M = 420.23

Orthorhombic,

a = 7.2340 (4) Å

b = 11.7610 (5) Å

c = 18.913 (1) Å

V = 1609.10 (14) Å3

Z = 4

Mo Kα radiation

μ = 1.40 mm−1

T = 292 (2) K

0.35 × 0.29 × 0.25 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.615, T max = 0.711

13881 measured reflections

3667 independent reflections

3083 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.085

S = 1.02

3667 reflections

207 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.50 e Å−3

Δρmin = −0.58 e Å−3

Absolute structure: Flack (1983 ▶), 1369 Friedel pairs

Flack parameter: 0.00 (3)

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807063672/ci2532sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807063672/ci2532Isup2.hkl

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

[Ag(C8H10NO3S)(C7H6N2)]·H2O	F000 = 848
Mr = 420.23	Dx = 1.735 Mg m−3
Orthorhombic, P212121	Mo Kα radiation λ = 0.71069 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3667 reflections
a = 7.2340 (4) Å	θ = 2.0–27.5º
b = 11.7610 (5) Å	µ = 1.40 mm−1
c = 18.913 (1) Å	T = 292 (2) K
V = 1609.10 (14) Å3	Block, yellow
Z = 4	0.35 × 0.29 × 0.25 mm

Rigaku R-AXIS RAPID diffractometer	3667 independent reflections
Radiation source: fine-focus sealed tube	3083 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.053
T = 292(2) K	θmax = 27.5º
ω scans	θmin = 2.0º
Absorption correction: multi-scan(ABSCOR; Higashi, 1995)	h = −9→9
Tmin = 0.615, Tmax = 0.711	k = −15→15
13881 measured reflections	l = −24→24

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.032	w = 1/[σ2(Fo2) + (0.0492P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.085	(Δ/σ)max = 0.001
S = 1.02	Δρmax = 0.50 e Å−3
3667 reflections	Δρmin = −0.58 e Å−3
207 parameters	Extinction correction: none
4 restraints	Absolute structure: Flack (1983), with 1369 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.00 (3)
Secondary atom site location: difference Fourier map

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	0.57509 (5)	0.32306 (3)	0.368222 (17)	0.04386 (11)
C1	0.1920 (5)	0.5165 (3)	0.4190 (2)	0.0308 (8)
C2	0.1248 (6)	0.6189 (4)	0.3919 (2)	0.0393 (10)
H2	0.0045	0.6211	0.3746	0.047*
C3	0.2286 (7)	0.7160 (4)	0.3898 (2)	0.0444 (11)
C4	0.4079 (8)	0.7131 (4)	0.4174 (2)	0.0455 (11)
C5	0.4746 (6)	0.6123 (4)	0.4454 (2)	0.0408 (10)
H5	0.5927	0.6113	0.4647	0.049*
C6	0.3719 (5)	0.5128 (3)	0.4457 (2)	0.0316 (9)
C7	0.5321 (8)	0.8154 (5)	0.4164 (3)	0.0684 (16)
H7A	0.4744	0.8765	0.4418	0.103*
H7B	0.5535	0.8383	0.3684	0.103*
H7C	0.6478	0.7967	0.4384	0.103*
C8	0.1486 (9)	0.8237 (4)	0.3565 (3)	0.0723 (16)
H8A	0.1767	0.8879	0.3859	0.108*
H8B	0.0169	0.8160	0.3521	0.108*
H8C	0.2018	0.8347	0.3105	0.108*
C9	0.3884 (6)	0.1510 (4)	0.2665 (2)	0.0455 (12)
H10	0.2963	0.2058	0.2704	0.055*
C10	0.3556 (7)	0.0582 (4)	0.2262 (3)	0.0493 (12)
H11	0.2415	0.0505	0.2040	0.059*
C11	0.6419 (6)	−0.0062 (4)	0.2511 (2)	0.0413 (10)
H12	0.7349	−0.0602	0.2459	0.050*
C12	0.6755 (6)	0.0873 (4)	0.2934 (2)	0.0410 (10)
C13	0.8545 (8)	0.1001 (6)	0.3321 (4)	0.078 (2)
H24A	0.8528	0.1694	0.3590	0.117*
H24B	0.9545	0.1024	0.2988	0.117*
H24C	0.8712	0.0368	0.3635	0.117*
N1	0.4536 (5)	0.4089 (3)	0.46717 (18)	0.0371 (8)
N2	0.5462 (5)	0.1673 (3)	0.30075 (16)	0.0366 (8)
N3	0.4829 (5)	−0.0226 (3)	0.21749 (19)	0.0435 (9)
O1	0.1454 (4)	0.3189 (3)	0.36351 (17)	0.0529 (8)
O2	0.0582 (5)	0.3433 (3)	0.48525 (17)	0.0518 (8)
O3	−0.1281 (4)	0.4287 (3)	0.3932 (2)	0.0573 (9)
O1W	−0.2470 (5)	0.4027 (3)	0.57266 (16)	0.0484 (8)
S1	0.05493 (14)	0.39276 (9)	0.41453 (6)	0.0369 (2)
H1N	0.539 (7)	0.421 (4)	0.495 (2)	0.055*
H2N	0.383 (6)	0.362 (3)	0.485 (2)	0.055*

	U11	U22	U33	U12	U13	U23
Ag1	0.04702 (19)	0.03504 (16)	0.04951 (17)	0.00277 (16)	−0.00239 (16)	−0.00726 (15)
C1	0.029 (2)	0.030 (2)	0.0339 (19)	−0.0029 (17)	0.0002 (16)	0.0016 (16)
C2	0.036 (2)	0.036 (2)	0.046 (2)	0.0036 (18)	−0.0017 (17)	−0.0005 (18)
C3	0.057 (3)	0.030 (2)	0.046 (2)	0.003 (2)	−0.003 (2)	0.0004 (18)
C4	0.054 (3)	0.037 (2)	0.045 (2)	−0.011 (2)	0.001 (2)	−0.0067 (18)
C5	0.036 (2)	0.041 (2)	0.045 (2)	−0.006 (2)	0.0013 (18)	−0.0043 (18)
C6	0.027 (2)	0.034 (2)	0.0334 (19)	0.0037 (17)	−0.0002 (15)	−0.0014 (16)
C7	0.078 (4)	0.050 (3)	0.077 (3)	−0.026 (3)	−0.005 (3)	0.002 (3)
C8	0.087 (4)	0.033 (2)	0.097 (4)	0.002 (3)	−0.014 (3)	0.012 (3)
C9	0.038 (3)	0.049 (3)	0.049 (2)	0.009 (2)	−0.0029 (19)	−0.012 (2)
C10	0.040 (2)	0.058 (3)	0.050 (3)	0.007 (2)	−0.012 (2)	−0.016 (2)
C11	0.038 (2)	0.036 (2)	0.050 (2)	0.0044 (19)	−0.001 (2)	−0.007 (2)
C12	0.039 (2)	0.038 (2)	0.046 (2)	−0.001 (2)	0.000 (2)	−0.001 (2)
C13	0.050 (3)	0.066 (4)	0.118 (5)	0.006 (3)	−0.031 (3)	−0.032 (4)
N1	0.031 (2)	0.0407 (19)	0.0398 (18)	0.0009 (16)	−0.0075 (16)	0.0044 (15)
N2	0.0350 (19)	0.0370 (18)	0.0377 (16)	−0.0004 (19)	0.0021 (14)	−0.0052 (15)
N3	0.047 (2)	0.041 (2)	0.0423 (19)	−0.0042 (19)	−0.0043 (17)	−0.0079 (16)
O1	0.0533 (18)	0.0402 (16)	0.0653 (19)	−0.0123 (17)	0.0106 (17)	−0.0140 (19)
O2	0.0434 (18)	0.049 (2)	0.0626 (18)	−0.0032 (17)	0.0058 (15)	0.0194 (15)
O3	0.0284 (16)	0.048 (2)	0.095 (3)	−0.0068 (14)	−0.0196 (16)	0.0175 (18)
O1W	0.0428 (18)	0.0499 (19)	0.0526 (18)	0.0038 (16)	−0.0054 (15)	0.0033 (15)
S1	0.0255 (5)	0.0328 (5)	0.0524 (6)	−0.0029 (4)	−0.0004 (5)	0.0053 (4)

Ag1—N2	2.243 (3)	C8—H8C	0.96
Ag1—N1	2.301 (4)	C9—N2	1.326 (6)
Ag1—N3i	2.469 (4)	C9—C10	1.353 (7)
Ag1—O3ii	2.525 (3)	C9—H10	0.9300
C1—C2	1.396 (6)	C10—N3	1.333 (6)
C1—C6	1.396 (6)	C10—H11	0.93
C1—S1	1.763 (4)	C11—N3	1.329 (5)
C2—C3	1.368 (6)	C11—C12	1.381 (6)
C2—H2	0.93	C11—H12	0.93
C3—C4	1.399 (8)	C12—N2	1.334 (6)
C3—C8	1.528 (7)	C12—C13	1.495 (7)
C4—C5	1.386 (6)	C13—H24A	0.96
C4—C7	1.501 (7)	C13—H24B	0.96
C5—C6	1.386 (6)	C13—H24C	0.96
C5—H5	0.93	N1—H1N	0.82 (5)
C6—N1	1.417 (5)	N1—H2N	0.82 (3)
C7—H7A	0.96	N3—Ag1iii	2.469 (4)
C7—H7B	0.96	O1—S1	1.454 (3)
C7—H7C	0.96	O2—S1	1.459 (3)
C8—H8A	0.96	O3—S1	1.448 (3)
C8—H8B	0.96	O3—Ag1iv	2.525 (3)
N2—Ag1—N1	141.78 (13)	N2—C9—H10	118.6
N2—Ag1—N3i	102.19 (12)	C10—C9—H10	118.6
N1—Ag1—N3i	98.44 (13)	N3—C10—C9	121.6 (4)
N2—Ag1—O3ii	125.98 (12)	N3—C10—H11	119.2
N1—Ag1—O3ii	87.53 (14)	C9—C10—H11	119.2
N3i—Ag1—O3ii	84.57 (12)	N3—C11—C12	123.1 (4)
C2—C1—C6	119.0 (4)	N3—C11—H12	118.5
C2—C1—S1	119.9 (3)	C12—C11—H12	118.5
C6—C1—S1	121.0 (3)	N2—C12—C11	119.9 (4)
C3—C2—C1	122.7 (4)	N2—C12—C13	119.0 (4)
C3—C2—H2	118.7	C11—C12—C13	121.1 (4)
C1—C2—H2	118.7	C12—C13—H24A	109.5
C2—C3—C4	118.6 (4)	C12—C13—H24B	109.5
C2—C3—C8	119.8 (5)	H24A—C13—H24B	109.5
C4—C3—C8	121.7 (4)	C12—C13—H24C	109.5
C5—C4—C3	119.1 (4)	H24A—C13—H24C	109.5
C5—C4—C7	118.8 (5)	H24B—C13—H24C	109.5
C3—C4—C7	122.1 (4)	C6—N1—Ag1	107.7 (2)
C4—C5—C6	122.5 (4)	C6—N1—H1N	111 (4)
C4—C5—H5	118.7	Ag1—N1—H1N	108 (3)
C6—C5—H5	118.7	C6—N1—H2N	116 (3)
C5—C6—C1	118.1 (4)	Ag1—N1—H2N	107 (3)
C5—C6—N1	120.4 (4)	H1N—N1—H2N	108 (4)
C1—C6—N1	121.3 (4)	C9—N2—C12	116.8 (4)
C4—C7—H7A	109.5	C9—N2—Ag1	118.4 (3)
C4—C7—H7B	109.5	C12—N2—Ag1	124.8 (3)
H7A—C7—H7B	109.5	C11—N3—C10	115.8 (4)
C4—C7—H7C	109.5	C11—N3—Ag1iii	124.6 (3)
H7A—C7—H7C	109.5	C10—N3—Ag1iii	119.2 (3)
H7B—C7—H7C	109.5	S1—O3—Ag1iv	133.33 (19)
C3—C8—H8A	109.5	O3—S1—O1	113.6 (2)
C3—C8—H8B	109.5	O3—S1—O2	112.8 (2)
H8A—C8—H8B	109.5	O1—S1—O2	111.3 (2)
C3—C8—H8C	109.5	O3—S1—C1	106.66 (19)
H8A—C8—H8C	109.5	O1—S1—C1	105.76 (18)
H8B—C8—H8C	109.5	O2—S1—C1	106.0 (2)
N2—C9—C10	122.8 (4)
C6—C1—C2—C3	0.6 (6)	C10—C9—N2—Ag1	−178.1 (4)
S1—C1—C2—C3	−175.8 (4)	C11—C12—N2—C9	0.6 (6)
C1—C2—C3—C4	−1.5 (7)	C13—C12—N2—C9	−178.7 (5)
C1—C2—C3—C8	177.4 (5)	C11—C12—N2—Ag1	179.1 (3)
C2—C3—C4—C5	0.4 (7)	C13—C12—N2—Ag1	−0.2 (6)
C8—C3—C4—C5	−178.4 (5)	N1—Ag1—N2—C9	63.6 (4)
C2—C3—C4—C7	179.3 (5)	N3i—Ag1—N2—C9	−57.6 (3)
C8—C3—C4—C7	0.4 (7)	O3ii—Ag1—N2—C9	−149.7 (3)
C3—C4—C5—C6	1.6 (7)	N1—Ag1—N2—C12	−114.9 (3)
C7—C4—C5—C6	−177.3 (4)	N3i—Ag1—N2—C12	124.0 (3)
C4—C5—C6—C1	−2.5 (6)	O3ii—Ag1—N2—C12	31.8 (4)
C4—C5—C6—N1	172.5 (4)	C12—C11—N3—C10	0.8 (7)
C2—C1—C6—C5	1.4 (6)	C12—C11—N3—Ag1iii	173.4 (3)
S1—C1—C6—C5	177.7 (3)	C9—C10—N3—C11	0.4 (7)
C2—C1—C6—N1	−173.6 (4)	C9—C10—N3—Ag1iii	−172.7 (4)
S1—C1—C6—N1	2.8 (5)	Ag1iv—O3—S1—O1	62.2 (4)
N2—C9—C10—N3	−1.1 (8)	Ag1iv—O3—S1—O2	−65.6 (4)
N3—C11—C12—N2	−1.3 (7)	Ag1iv—O3—S1—C1	178.4 (3)
N3—C11—C12—C13	177.9 (5)	C2—C1—S1—O3	−10.7 (4)
C5—C6—N1—Ag1	−90.6 (4)	C6—C1—S1—O3	172.9 (3)
C1—C6—N1—Ag1	84.2 (4)	C2—C1—S1—O1	110.6 (3)
N2—Ag1—N1—C6	−116.6 (3)	C6—C1—S1—O1	−65.8 (4)
N3i—Ag1—N1—C6	5.7 (3)	C2—C1—S1—O2	−131.2 (3)
O3ii—Ag1—N1—C6	89.8 (3)	C6—C1—S1—O2	52.5 (4)
C10—C9—N2—C12	0.5 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H2N···O2	0.82 (3)	2.36 (4)	2.982 (5)	133 (4)
N1—H1N···O1Wii	0.82 (5)	2.15 (5)	2.946 (5)	164 (5)

Ag1—N2	2.243 (3)
Ag1—N1	2.301 (4)
Ag1—N3i	2.469 (4)
Ag1—O3ii	2.525 (3)

N2—Ag1—N1	141.78 (13)
N2—Ag1—N3i	102.19 (12)
N1—Ag1—N3i	98.44 (13)
N2—Ag1—O3ii	125.98 (12)
N1—Ag1—O3ii	87.53 (14)
N3i—Ag1—O3ii	84.57 (12)

Symmetry codes: (i) ; (ii) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H2N⋯O2	0.82 (3)	2.36 (4)	2.982 (5)	133 (4)
N1—H1N⋯O1Wii	0.82 (5)	2.15 (5)	2.946 (5)	164 (5)

Symmetry code: (ii) .