catena-Poly[silver(I)-μ-4-amino­benzene­sulfonato-μ-2,3-diethyl­pyrazine]

In the title compound, [Ag(C₆H₆NO₃S)(C₈H₈N₂)], the Ag^I cation is four-coordinated by three N atoms from two different 2,3-diethyl­pyrazine ligands and one –NH₂ group of a 4-amino­benzene­sulfonate ligand, and one sulfonate O atom in a distorted tetra­hedral coordination geometry. The Ag^I centers are doubly bridged by both types of ligands, forming a one-dimensional chain. N—H...O hydrogen bonds complete the structure.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.034
• wR factor = 0.079
• Data-to-parameter ratio = 16.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.18
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         S1
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           27.46
           From the CIF: _reflns_number_total               3443
           Count of symmetry unique reflns         1813
           Completeness (_total/calc)            189.91%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1630
           Fraction of Friedel pairs measured     0.899
           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 .......          3

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   4 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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

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S1. Comment

Silver(I) sulfonate coordination polymers have received much attention for their interesting structural features and potential application (Cote & Shimizu, 2003). Recently, silver(I) sulfonate compounds with nitrogen-based secondary ligands have been studied (Liu et al., 2007). Herein, we present a new sulfonate coordination polymer, namely [Ag(dep)(L)] (I), where dep = 2,3-diethylpyrazine and HL= 4-aminobenzenesulfonic acid. To our knowledge, this is the first complex reported which contains dep as a ligand.

Selected parameters are listed in Table 1. The Ag^I cation is four-coordinated by three N atoms from two different dep ligands and one –NH₂ group of L, and one sulfonate O atom in a distorted tetrahedral coordination geometry (Fig. 1). The Ag—N distances in (I) are similar to those in related compounds (Liu et al., 2007). The Ag^I centers are doubly bridged by both types of ligands to form a one-dimensional chain (Fig. 2). Finally, N—H···O hydrogen bonds complete the structure of (I) (Table 2).

Related literature

For studies on silver sulfonates, see Liu et al., (2007). For related literature, see: Cote & Shimizu (2003).

S2. Experimental

An aqueous solution (16 ml) of 4-aminobenzenesulfonic acid (1 mmol) was added to solid Ag₂CO₃ (0.5 mmol) and stirred for several minutes until no further CO₂ was given off. The 2,3-diethylpyrazine (1 mmol) was then added and a precipitate was formed. The precipitate was dissolved by ammonium hydroxide. Crystals of (I) were obtained by evaporation of the solution for one week at room temperature.

S3. Refinement

H atoms of C atoms were positioned geometrically (C—H = 0.93 Å) and refined as riding, with U_iso(H)=1.2U_eq(carrier). H atoms bonded to N atom were located in a difference map and refined freely, and with U_iso(H) = 1.2U_eq(N).

Computing details

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

	Fig. 1. The structure of (I), showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Symmetry code: (i) 1.5 - x, y, z - 1/2; (ii) 1.5 - x, y, z + 1/2.
	Fig. 2. View of the chain structure of (I).

catena-Poly[silver(I)-µ-4-aminobenzenesulfonato-µ-2,3-diethylpyrazine]

Crystal data

[Ag(C6H6NO3S)(C8H8N2)]	F(000) = 840
Mr = 416.24	Dx = 1.817 Mg m^−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 11246 reflections
a = 8.6095 (17) Å	θ = 3.0–27.5°
b = 12.322 (3) Å	µ = 1.48 mm^−1
c = 14.342 (3) Å	T = 293 K
V = 1521.5 (5) Å^3	Block, colourless
Z = 4	0.31 × 0.22 × 0.17 mm

Data collection

Rigaku R-AXIS RAPID CCD diffractometer	3443 independent reflections
Radiation source: rotating anode	2756 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
Detector resolution: 10.0 pixels mm^-1	θmax = 27.5°, θmin = 3.2°
ω scans	h = −11→11
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −15→15
Tmin = 0.626, Tmax = 0.779	l = −18→18
13887 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.079	w = 1/[σ^2(Fo^2) + (0.0361P)^2 + 0.2752P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
3443 reflections	Δρmax = 0.68 e Å^−3
207 parameters	Δρmin = −0.31 e Å^−3
3 restraints	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.02 (4)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Ag1	0.75241 (4)	0.26431 (3)	0.84998 (7)	0.04695 (10)
N2	0.7161 (4)	0.2166 (3)	0.6974 (3)	0.0320 (8)
N3	0.5572 (4)	0.3870 (4)	0.8990 (2)	0.0418 (9)
C2	0.3331 (4)	0.3028 (3)	1.1066 (3)	0.0314 (7)
H2	0.2491	0.2583	1.1208	0.038*
C1	0.4096 (4)	0.3569 (4)	1.1770 (2)	0.0309 (9)
C5	0.5817 (5)	0.4358 (4)	1.0639 (3)	0.0370 (10)
H5	0.6650	0.4808	1.0493	0.044*
C4	0.5046 (4)	0.3807 (3)	0.9936 (3)	0.0329 (8)
C3	0.3805 (4)	0.3143 (4)	1.0149 (3)	0.0335 (10)
H3	0.3287	0.2773	0.9677	0.040*
C15	0.6074 (5)	0.2709 (4)	0.6484 (3)	0.0379 (12)
H15	0.5352	0.3134	0.6800	0.046*
C16	0.8158 (4)	0.1530 (4)	0.6489 (3)	0.0297 (9)
C17	0.9340 (5)	0.0913 (4)	0.7056 (3)	0.0369 (10)
H17A	1.0324	0.0920	0.6727	0.044*
H17B	0.9489	0.1284	0.7646	0.044*
C18	0.8893 (6)	−0.0230 (5)	0.7244 (4)	0.0603 (15)
H18A	0.9691	−0.0576	0.7606	0.090*
H18B	0.8766	−0.0609	0.6664	0.090*
H18C	0.7933	−0.0245	0.7584	0.090*
C6	0.5349 (5)	0.4242 (4)	1.1560 (3)	0.0360 (10)
H6	0.5868	0.4610	1.2032	0.043*
O2	0.2572 (3)	0.4407 (3)	1.3140 (2)	0.0509 (8)
O3	0.4825 (3)	0.3370 (3)	1.3513 (2)	0.0602 (9)
O1	0.2466 (4)	0.2486 (3)	1.2958 (3)	0.0693 (14)
S1	0.34471 (10)	0.34335 (8)	1.29348 (7)	0.0329 (2)
C10	0.6010 (5)	0.2649 (4)	0.5534 (3)	0.0349 (11)
H10	0.5247	0.3036	0.5217	0.042*
N1	0.7017 (4)	0.2050 (4)	0.5049 (3)	0.0334 (8)
C11	0.8082 (5)	0.1482 (4)	0.5518 (3)	0.0325 (10)
C12	0.9145 (5)	0.0780 (4)	0.4936 (3)	0.0429 (11)
H12A	1.0060	0.0605	0.5301	0.051*
H12B	0.9483	0.1193	0.4397	0.051*
C13	0.8404 (7)	−0.0264 (5)	0.4606 (4)	0.0612 (15)
H13A	0.9143	−0.0670	0.4246	0.092*
H13B	0.7516	−0.0098	0.4227	0.092*
H13C	0.8084	−0.0684	0.5135	0.092*
HN1	0.475 (3)	0.378 (4)	0.866 (3)	0.054 (15)*
HN2	0.605 (5)	0.447 (2)	0.895 (4)	0.064 (17)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ag1	0.04408 (15)	0.0751 (2)	0.02168 (13)	−0.00020 (18)	0.00003 (12)	−0.0028 (3)
N2	0.0346 (16)	0.039 (2)	0.0222 (18)	0.0021 (16)	−0.0005 (16)	0.0016 (16)
N3	0.040 (2)	0.058 (3)	0.0277 (17)	0.0066 (18)	0.0032 (16)	0.0097 (17)
C2	0.0300 (16)	0.0350 (19)	0.0292 (18)	−0.0006 (13)	0.000 (2)	0.0033 (19)
C1	0.0307 (18)	0.038 (3)	0.0240 (17)	0.0030 (16)	0.0004 (14)	−0.0017 (17)
C5	0.035 (2)	0.033 (3)	0.043 (2)	−0.0019 (18)	0.0019 (19)	0.0040 (18)
C4	0.0346 (19)	0.037 (2)	0.0274 (17)	0.0097 (17)	0.0035 (16)	0.0046 (17)
C3	0.0314 (19)	0.042 (3)	0.027 (2)	0.0023 (17)	−0.0059 (16)	−0.0020 (18)
C15	0.032 (2)	0.051 (4)	0.030 (2)	0.009 (2)	0.001 (2)	−0.004 (2)
C16	0.028 (2)	0.035 (3)	0.0264 (19)	0.0024 (19)	−0.0020 (17)	−0.0008 (18)
C17	0.035 (2)	0.039 (3)	0.037 (2)	0.0042 (18)	−0.0093 (19)	0.0038 (19)
C18	0.070 (3)	0.044 (3)	0.067 (3)	0.000 (3)	−0.022 (3)	0.017 (3)
C6	0.039 (2)	0.036 (3)	0.034 (2)	0.0005 (18)	−0.0047 (18)	−0.0021 (18)
O2	0.0565 (18)	0.057 (2)	0.0394 (16)	0.0259 (15)	0.0059 (13)	−0.0043 (14)
O3	0.0433 (15)	0.109 (3)	0.0280 (14)	0.0254 (17)	−0.0057 (14)	0.007 (2)
O1	0.109 (4)	0.060 (3)	0.039 (2)	−0.040 (2)	0.027 (2)	−0.0145 (15)
S1	0.0359 (4)	0.0391 (5)	0.0235 (4)	0.0027 (4)	−0.0001 (4)	−0.0027 (4)
C10	0.032 (2)	0.041 (3)	0.032 (2)	0.008 (2)	−0.0043 (18)	0.0017 (19)
N1	0.0310 (16)	0.044 (2)	0.0247 (19)	−0.0011 (18)	0.0029 (17)	0.0011 (17)
C11	0.031 (2)	0.036 (3)	0.031 (2)	−0.003 (2)	0.0013 (17)	0.0013 (18)
C12	0.034 (2)	0.056 (3)	0.039 (2)	0.003 (2)	0.0070 (19)	−0.007 (2)
C13	0.060 (3)	0.064 (4)	0.060 (3)	−0.005 (3)	0.011 (3)	−0.028 (3)

Geometric parameters (Å, º)

Ag1—N2	2.287 (4)	C17—C18	1.486 (7)
Ag1—N3	2.367 (4)	C17—H17A	0.9700
Ag1—N1^i	2.372 (4)	C17—H17B	0.9700
Ag1—O3^ii	2.451 (3)	C18—H18A	0.9600
N2—C15	1.348 (6)	C18—H18B	0.9600
N2—C16	1.355 (6)	C18—H18C	0.9600
N3—C4	1.432 (5)	C6—H6	0.9300
N3—HN1	0.86 (3)	O2—S1	1.446 (3)
N3—HN2	0.85 (3)	O3—S1	1.450 (3)
C2—C1	1.378 (5)	O3—Ag1^i	2.451 (3)
C2—C3	1.384 (6)	O1—S1	1.441 (3)
C2—H2	0.9300	C10—N1	1.334 (6)
C1—C6	1.393 (6)	C10—H10	0.9300
C1—S1	1.769 (4)	N1—C11	1.335 (6)
C5—C4	1.385 (6)	N1—Ag1^ii	2.372 (4)
C5—C6	1.388 (6)	C11—C12	1.510 (6)
C5—H5	0.9300	C12—C13	1.512 (7)
C4—C3	1.380 (6)	C12—H12A	0.9700
C3—H3	0.9300	C12—H12B	0.9700
C15—C10	1.367 (5)	C13—H13A	0.9600
C15—H15	0.9300	C13—H13B	0.9600
C16—C11	1.395 (4)	C13—H13C	0.9600
C16—C17	1.508 (6)
N2—Ag1—N3	110.54 (13)	C16—C17—H17B	108.8
N2—Ag1—N1^i	147.11 (11)	H17A—C17—H17B	107.7
N3—Ag1—N1^i	92.12 (13)	C17—C18—H18A	109.5
N2—Ag1—O3^ii	103.22 (13)	C17—C18—H18B	109.5
N3—Ag1—O3^ii	115.15 (14)	H18A—C18—H18B	109.5
N1^i—Ag1—O3^ii	87.14 (12)	C17—C18—H18C	109.5
C15—N2—C16	117.3 (4)	H18A—C18—H18C	109.5
C15—N2—Ag1	117.8 (3)	H18B—C18—H18C	109.5
C16—N2—Ag1	123.6 (3)	C5—C6—C1	119.5 (4)
C4—N3—Ag1	118.1 (3)	C5—C6—H6	120.2
C4—N3—HN1	104 (3)	C1—C6—H6	120.2
Ag1—N3—HN1	110 (3)	S1—O3—Ag1^i	141.0 (2)
C4—N3—HN2	105 (4)	O1—S1—O2	111.2 (2)
Ag1—N3—HN2	101 (4)	O1—S1—O3	115.0 (3)
HN1—N3—HN2	118 (5)	O2—S1—O3	110.8 (2)
C1—C2—C3	120.4 (4)	O1—S1—C1	106.5 (2)
C1—C2—H2	119.8	O2—S1—C1	106.1 (2)
C3—C2—H2	119.8	O3—S1—C1	106.67 (18)
C2—C1—C6	119.9 (3)	N1—C10—C15	121.6 (5)
C2—C1—S1	119.7 (3)	N1—C10—H10	119.2
C6—C1—S1	120.4 (3)	C15—C10—H10	119.2
C4—C5—C6	120.2 (4)	C10—N1—C11	118.3 (4)
C4—C5—H5	119.9	C10—N1—Ag1^ii	115.2 (3)
C6—C5—H5	119.9	C11—N1—Ag1^ii	121.2 (3)
C3—C4—C5	120.0 (4)	N1—C11—C16	120.8 (5)
C3—C4—N3	119.2 (4)	N1—C11—C12	116.0 (4)
C5—C4—N3	120.7 (4)	C16—C11—C12	123.2 (5)
C4—C3—C2	120.0 (4)	C11—C12—C13	113.8 (4)
C4—C3—H3	120.0	C11—C12—H12A	108.8
C2—C3—H3	120.0	C13—C12—H12A	108.8
N2—C15—C10	121.4 (5)	C11—C12—H12B	108.8
N2—C15—H15	119.3	C13—C12—H12B	108.8
C10—C15—H15	119.3	H12A—C12—H12B	107.7
N2—C16—C11	120.5 (5)	C12—C13—H13A	109.5
N2—C16—C17	116.2 (3)	C12—C13—H13B	109.5
C11—C16—C17	123.3 (5)	H13A—C13—H13B	109.5
C18—C17—C16	113.7 (4)	C12—C13—H13C	109.5
C18—C17—H17A	108.8	H13A—C13—H13C	109.5
C16—C17—H17A	108.8	H13B—C13—H13C	109.5
C18—C17—H17B	108.8
N3—Ag1—N2—C15	8.8 (4)	C4—C5—C6—C1	−0.2 (7)
N1^i—Ag1—N2—C15	139.5 (3)	C2—C1—C6—C5	−0.1 (7)
O3^ii—Ag1—N2—C15	−114.9 (3)	S1—C1—C6—C5	−178.4 (4)
N3—Ag1—N2—C16	175.5 (4)	Ag1^i—O3—S1—O1	82.1 (4)
N1^i—Ag1—N2—C16	−53.8 (5)	Ag1^i—O3—S1—O2	−150.8 (3)
O3^ii—Ag1—N2—C16	51.8 (4)	Ag1^i—O3—S1—C1	−35.7 (4)
N2—Ag1—N3—C4	145.8 (3)	C2—C1—S1—O1	17.3 (4)
N1^i—Ag1—N3—C4	−9.9 (3)	C6—C1—S1—O1	−164.4 (4)
O3^ii—Ag1—N3—C4	−97.7 (3)	C2—C1—S1—O2	−101.3 (4)
C3—C2—C1—C6	0.4 (6)	C6—C1—S1—O2	77.0 (4)
C3—C2—C1—S1	178.7 (3)	C2—C1—S1—O3	140.5 (3)
C6—C5—C4—C3	0.3 (7)	C6—C1—S1—O3	−41.2 (4)
C6—C5—C4—N3	−176.3 (4)	N2—C15—C10—N1	0.1 (9)
Ag1—N3—C4—C3	−90.5 (4)	C15—C10—N1—C11	1.5 (8)
Ag1—N3—C4—C5	86.1 (5)	C15—C10—N1—Ag1^ii	−153.2 (5)
C5—C4—C3—C2	0.0 (6)	C10—N1—C11—C16	−1.2 (8)
N3—C4—C3—C2	176.7 (4)	Ag1^ii—N1—C11—C16	151.9 (4)
C1—C2—C3—C4	−0.3 (6)	C10—N1—C11—C12	177.5 (4)
C16—N2—C15—C10	−2.1 (8)	Ag1^ii—N1—C11—C12	−29.4 (6)
Ag1—N2—C15—C10	165.5 (5)	N2—C16—C11—N1	−0.7 (9)
C15—N2—C16—C11	2.3 (8)	C17—C16—C11—N1	−179.6 (4)
Ag1—N2—C16—C11	−164.4 (4)	N2—C16—C11—C12	−179.3 (4)
C15—N2—C16—C17	−178.7 (4)	C17—C16—C11—C12	1.9 (9)
Ag1—N2—C16—C17	14.5 (6)	N1—C11—C12—C13	−77.5 (6)
N2—C16—C17—C18	98.0 (5)	C16—C11—C12—C13	101.2 (6)
C11—C16—C17—C18	−83.1 (6)

Symmetry codes: (i) −x+3/2, y, z+1/2; (ii) −x+3/2, y, z−1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—HN2···O2^iii	0.85 (3)	2.16 (3)	2.923 (6)	149 (5)
N3—HN1···O2^iv	0.86 (3)	2.27 (3)	3.042 (5)	150 (4)

Symmetry codes: (iii) −x+1, −y+1, z−1/2; (iv) −x+1/2, y, z−1/2.