Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807021897/hb2404sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807021897/hb2404Isup2.hkl |
CCDC reference: 650605
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.005 Å
- R factor = 0.038
- wR factor = 0.100
- Data-to-parameter ratio = 17.6
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C8
Alert level G PLAT794_ALERT_5_G Check Predicted Bond Valency for Ag1 (9) 1.00
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
The related compound, [Ag(L)(bipy)] (bipy = 2,2'-bipyridine), has a mononuclear structure in which the AgI cation is three-coordinated by two N atoms from one bipy molecule and one N atom from a L anion in a highly distorted trigonal-planar geometry. An intramolecular N—H···O hydrogen bond helps to establish the molecular conformation (Liu et al., 2006). For related literature, see: May & Shimizu (2005); Sun et al. (2004); You & Zhu (2004).
To a mixture of HL (0.5 mmol) and NaOH (0.5 mmol) in water was added AgNO3 (0.5 mmol) with constant stirring, to which was added bbi (0.5 mmol) in water. After the sample was stirred for 5 min, the precipitate was dissolved by dropwise addition of aqueous NH3 solution. Colorless crystals of (I) were obtained from the filtrate by slow evaporation after standing in the dark for three days (45% yield).
The H atoms bonded to N atom were located in a difference map and their positions were refined freely, with Uiso(H) = 1.2Ueq(N). The C-bound H atoms were positioned geometrically (C—H = 0.93 Å) and refined as riding, with Uiso(H)=1.2Ueq(carrier).
Recently, intense interest has been focused on silver(I) sulfonates due to their interesting structures and properties (May & Shimizu, 2005). Based on previous reports, the structure motif of most silver(I) sulfonates observed is a two-dimensional layer, which is similar to that of metal phosphonates (Sun et al., 2004). So far, some silver(I) sulfonate compounds modified by nitrogen-based ligands that display different structure motifs depending upon the presence of secondary ligands have been reported (You et al., 2004). However, the information on silver sulfonate coordination polymers are not yet well understood, especially, investigations of silver(I) sulfonates with neutral ligands are rather insufficient. We selected 2-amino-3,5-dimethylbenzenesulfonic acid (HL) as a sulfonate ligand and 1,1'-(1,4-butanediyl)-bis(imidazole) (bbi) as a secondary ligand, generating a new chain coordination polymer, [Ag(L)(bbi)], (I), which is reported here.
In compound (I), each AgI cation is three-coordinated by two N atoms from two different bbi ligands, and one sulfonate O atom from one L anion in a distorted trigonal-planar geometry (Fig. 1, Table 1). As shown in Fig. 2, each bbi moiety acts as a bidentate ligand that binds two AgI atoms, thus forming a one-dimensional chain. The L anions are attached on both sides of the chain through the Ag—O bonds. Moreover, N—H···O hydrogen bonds (Table 2) link the chains together, reinforcing the crystal cohesion of (I).
The related compound, [Ag(L)(bipy)] (bipy = 2,2'-bipyridine), has a mononuclear structure in which the AgI cation is three-coordinated by two N atoms from one bipy molecule and one N atom from a L anion in a highly distorted trigonal-planar geometry. An intramolecular N—H···O hydrogen bond helps to establish the molecular conformation (Liu et al., 2006). For related literature, see: May & Shimizu (2005); Sun et al. (2004); You & Zhu (2004).
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.
[Ag(C8H10NO3S)(C10H14N4)] | F(000) = 1016 |
Mr = 498.35 | Dx = 1.610 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 13313 reflections |
a = 8.6632 (17) Å | θ = 3.3–27.5° |
b = 17.239 (3) Å | µ = 1.11 mm−1 |
c = 13.789 (3) Å | T = 292 K |
β = 93.11 (3)° | Block, colorless |
V = 2056.3 (7) Å3 | 0.31 × 0.27 × 0.24 mm |
Z = 4 |
Rigaku R-AXIS RAPID diffractometer | 4617 independent reflections |
Radiation source: rotating anode | 2695 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.050 |
Detector resolution: 10.0 pixels mm-1 | θmax = 27.5°, θmin = 1.9° |
ω scans | h = −11→10 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −21→22 |
Tmin = 0.703, Tmax = 0.764 | l = −17→17 |
17540 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.038 | Hydrogen site location: difmap and geom |
wR(F2) = 0.100 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.98 | w = 1/[σ2(Fo2) + (0.0495P)2] where P = (Fo2 + 2Fc2)/3 |
4617 reflections | (Δ/σ)max = 0.001 |
263 parameters | Δρmax = 0.71 e Å−3 |
0 restraints | Δρmin = −0.69 e Å−3 |
[Ag(C8H10NO3S)(C10H14N4)] | V = 2056.3 (7) Å3 |
Mr = 498.35 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.6632 (17) Å | µ = 1.11 mm−1 |
b = 17.239 (3) Å | T = 292 K |
c = 13.789 (3) Å | 0.31 × 0.27 × 0.24 mm |
β = 93.11 (3)° |
Rigaku R-AXIS RAPID diffractometer | 4617 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 2695 reflections with I > 2σ(I) |
Tmin = 0.703, Tmax = 0.764 | Rint = 0.050 |
17540 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.100 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.98 | Δρmax = 0.71 e Å−3 |
4617 reflections | Δρmin = −0.69 e Å−3 |
263 parameters |
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 | ||
C1 | 0.9861 (4) | 0.11829 (16) | −0.1790 (2) | 0.0349 (8) | |
C2 | 1.0868 (4) | 0.11463 (17) | −0.0946 (2) | 0.0363 (8) | |
C3 | 1.2453 (4) | 0.12822 (18) | −0.1037 (3) | 0.0403 (8) | |
C4 | 1.2984 (4) | 0.14376 (19) | −0.1950 (3) | 0.0469 (9) | |
H4 | 1.4037 | 0.1519 | −0.2007 | 0.056* | |
C5 | 1.2009 (4) | 0.14763 (19) | −0.2781 (3) | 0.0466 (9) | |
C6 | 1.0449 (4) | 0.13536 (17) | −0.2681 (2) | 0.0426 (8) | |
H6 | 0.9774 | 0.1387 | −0.3227 | 0.051* | |
C7 | 1.2654 (6) | 0.1640 (3) | −0.3765 (3) | 0.0840 (15) | |
H7A | 1.3622 | 0.1909 | −0.3673 | 0.126* | |
H7B | 1.1936 | 0.1956 | −0.4145 | 0.126* | |
H7C | 1.2813 | 0.1160 | −0.4097 | 0.126* | |
C8 | 1.3569 (4) | 0.1259 (2) | −0.0155 (3) | 0.0624 (11) | |
H8A | 1.3278 | 0.1644 | 0.0304 | 0.094* | |
H8B | 1.4596 | 0.1364 | −0.0348 | 0.094* | |
H8C | 1.3540 | 0.0755 | 0.0139 | 0.094* | |
C9 | −0.1508 (4) | 0.0935 (2) | 0.4814 (3) | 0.0509 (9) | |
H9A | −0.1969 | 0.0682 | 0.5319 | 0.061* | |
C10 | −0.0880 (4) | 0.0588 (2) | 0.4058 (3) | 0.0506 (10) | |
H10A | −0.0833 | 0.0057 | 0.3946 | 0.061* | |
C11 | −0.0647 (4) | 0.18262 (19) | 0.3921 (3) | 0.0482 (9) | |
H11A | −0.0394 | 0.2312 | 0.3682 | 0.058* | |
C12 | 0.6619 (4) | 0.0826 (2) | 0.1489 (3) | 0.0503 (10) | |
H12 | 0.6945 | 0.0514 | 0.0990 | 0.060* | |
C13 | 0.5835 (4) | 0.0580 (2) | 0.2255 (3) | 0.0498 (9) | |
H13 | 0.5521 | 0.0075 | 0.2374 | 0.060* | |
C14 | 0.6224 (4) | 0.1819 (2) | 0.2376 (3) | 0.0455 (9) | |
H14 | 0.6216 | 0.2324 | 0.2613 | 0.055* | |
C15 | 0.0521 (4) | 0.1066 (2) | 0.2605 (3) | 0.0557 (10) | |
H15A | 0.0006 | 0.1361 | 0.2083 | 0.067* | |
H15B | 0.0506 | 0.0524 | 0.2414 | 0.067* | |
C16 | 0.2177 (4) | 0.1334 (2) | 0.2742 (3) | 0.0597 (11) | |
H16A | 0.2674 | 0.1268 | 0.2133 | 0.072* | |
H16B | 0.2181 | 0.1884 | 0.2891 | 0.072* | |
C17 | 0.3117 (4) | 0.0917 (3) | 0.3527 (3) | 0.0606 (11) | |
H17A | 0.3181 | 0.0373 | 0.3355 | 0.073* | |
H17B | 0.2584 | 0.0951 | 0.4127 | 0.073* | |
C18 | 0.4740 (4) | 0.1231 (3) | 0.3706 (3) | 0.0646 (11) | |
H18A | 0.4690 | 0.1761 | 0.3939 | 0.078* | |
H18B | 0.5285 | 0.0923 | 0.4205 | 0.078* | |
N1 | 1.0317 (5) | 0.1013 (2) | −0.0026 (2) | 0.0518 (8) | |
N2 | −0.0326 (3) | 0.11565 (15) | 0.3484 (2) | 0.0419 (7) | |
N3 | −0.1360 (3) | 0.17177 (17) | 0.4721 (2) | 0.0485 (8) | |
N4 | 0.6856 (3) | 0.16103 (17) | 0.1567 (2) | 0.0476 (7) | |
N5 | 0.5597 (3) | 0.12121 (17) | 0.2814 (2) | 0.0445 (7) | |
O1 | 0.7257 (3) | 0.16763 (13) | −0.1191 (2) | 0.0567 (7) | |
O2 | 0.7185 (3) | 0.09931 (16) | −0.2709 (2) | 0.0682 (8) | |
O3 | 0.7705 (3) | 0.02929 (13) | −0.1206 (2) | 0.0617 (8) | |
S1 | 0.78366 (10) | 0.10201 (5) | −0.17196 (7) | 0.0420 (2) | |
Ag1 | 0.78216 (4) | 0.23648 (2) | 0.05684 (3) | 0.07189 (16) | |
H1A | 0.945 (5) | 0.081 (2) | −0.003 (3) | 0.052 (13)* | |
H1B | 1.101 (4) | 0.079 (2) | 0.041 (3) | 0.056 (12)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.043 (2) | 0.0287 (16) | 0.033 (2) | 0.0022 (14) | 0.0029 (16) | −0.0007 (13) |
C2 | 0.044 (2) | 0.0316 (17) | 0.034 (2) | 0.0016 (14) | 0.0070 (16) | −0.0006 (13) |
C3 | 0.044 (2) | 0.0363 (18) | 0.040 (2) | −0.0019 (15) | −0.0024 (17) | 0.0019 (15) |
C4 | 0.045 (2) | 0.041 (2) | 0.055 (3) | −0.0021 (15) | 0.010 (2) | 0.0000 (16) |
C5 | 0.060 (3) | 0.046 (2) | 0.035 (2) | −0.0056 (17) | 0.0146 (19) | −0.0003 (16) |
C6 | 0.060 (2) | 0.0356 (18) | 0.032 (2) | −0.0013 (16) | 0.0001 (17) | 0.0003 (14) |
C7 | 0.097 (4) | 0.111 (4) | 0.047 (3) | −0.029 (3) | 0.026 (3) | 0.003 (2) |
C8 | 0.049 (2) | 0.080 (3) | 0.057 (3) | −0.008 (2) | −0.009 (2) | 0.012 (2) |
C9 | 0.050 (2) | 0.060 (3) | 0.043 (2) | 0.0042 (18) | 0.0026 (18) | 0.0067 (18) |
C10 | 0.055 (2) | 0.037 (2) | 0.059 (3) | 0.0012 (17) | −0.001 (2) | 0.0004 (17) |
C11 | 0.060 (2) | 0.0362 (19) | 0.049 (3) | 0.0074 (17) | 0.007 (2) | −0.0004 (16) |
C12 | 0.043 (2) | 0.058 (2) | 0.050 (3) | −0.0057 (18) | 0.0050 (19) | −0.0118 (18) |
C13 | 0.046 (2) | 0.046 (2) | 0.058 (3) | −0.0095 (17) | 0.0064 (19) | 0.0057 (18) |
C14 | 0.039 (2) | 0.045 (2) | 0.052 (3) | −0.0072 (16) | −0.0029 (18) | −0.0025 (17) |
C15 | 0.047 (2) | 0.076 (3) | 0.043 (2) | 0.0123 (19) | 0.0011 (18) | −0.0071 (19) |
C16 | 0.055 (3) | 0.083 (3) | 0.041 (2) | 0.007 (2) | 0.014 (2) | 0.008 (2) |
C17 | 0.048 (2) | 0.095 (3) | 0.041 (2) | −0.002 (2) | 0.0167 (19) | 0.009 (2) |
C18 | 0.046 (2) | 0.107 (3) | 0.041 (3) | −0.012 (2) | 0.0067 (19) | −0.002 (2) |
N1 | 0.051 (2) | 0.070 (2) | 0.034 (2) | −0.0012 (19) | 0.0039 (17) | 0.0069 (16) |
N2 | 0.0392 (16) | 0.0452 (17) | 0.0414 (18) | 0.0083 (13) | 0.0012 (13) | −0.0061 (13) |
N3 | 0.0490 (19) | 0.054 (2) | 0.043 (2) | 0.0145 (14) | 0.0036 (15) | −0.0046 (14) |
N4 | 0.0407 (18) | 0.0587 (19) | 0.043 (2) | −0.0107 (14) | 0.0018 (15) | 0.0050 (14) |
N5 | 0.0377 (17) | 0.0597 (19) | 0.0362 (18) | −0.0071 (14) | 0.0031 (13) | −0.0034 (14) |
O1 | 0.0463 (15) | 0.0505 (15) | 0.074 (2) | 0.0030 (11) | 0.0116 (14) | −0.0132 (13) |
O2 | 0.0563 (17) | 0.092 (2) | 0.0547 (19) | −0.0096 (14) | −0.0140 (14) | −0.0007 (16) |
O3 | 0.0518 (16) | 0.0430 (14) | 0.090 (2) | −0.0092 (12) | 0.0051 (15) | 0.0192 (13) |
S1 | 0.0400 (5) | 0.0395 (5) | 0.0460 (6) | −0.0017 (4) | −0.0010 (4) | 0.0007 (4) |
Ag1 | 0.0656 (2) | 0.0907 (3) | 0.0585 (2) | −0.03257 (18) | −0.00434 (16) | 0.02951 (18) |
C1—C6 | 1.386 (4) | C12—H12 | 0.9300 |
C1—C2 | 1.418 (5) | C13—N5 | 1.357 (4) |
C1—S1 | 1.784 (3) | C13—H13 | 0.9300 |
C2—N1 | 1.399 (4) | C14—N4 | 1.319 (4) |
C2—C3 | 1.405 (5) | C14—N5 | 1.337 (4) |
C3—C4 | 1.389 (5) | C14—H14 | 0.9300 |
C3—C8 | 1.513 (5) | C15—N2 | 1.460 (4) |
C4—C5 | 1.388 (5) | C15—C16 | 1.509 (5) |
C4—H4 | 0.9300 | C15—H15A | 0.9700 |
C5—C6 | 1.382 (5) | C15—H15B | 0.9700 |
C5—C7 | 1.522 (5) | C16—C17 | 1.502 (6) |
C6—H6 | 0.9300 | C16—H16A | 0.9700 |
C7—H7A | 0.9600 | C16—H16B | 0.9700 |
C7—H7B | 0.9600 | C17—C18 | 1.515 (5) |
C7—H7C | 0.9600 | C17—H17A | 0.9700 |
C8—H8A | 0.9600 | C17—H17B | 0.9700 |
C8—H8B | 0.9600 | C18—N5 | 1.472 (4) |
C8—H8C | 0.9600 | C18—H18A | 0.9700 |
C9—C10 | 1.343 (5) | C18—H18B | 0.9700 |
C9—N3 | 1.362 (4) | N1—H1A | 0.83 (4) |
C9—H9A | 0.9300 | N1—H1B | 0.92 (4) |
C10—N2 | 1.363 (4) | O1—S1 | 1.450 (2) |
C10—H10A | 0.9300 | O2—S1 | 1.448 (3) |
C11—N3 | 1.307 (4) | O3—S1 | 1.447 (2) |
C11—N2 | 1.338 (4) | Ag1—N4 | 2.101 (3) |
C11—H11A | 0.9300 | Ag1—N3i | 2.112 (3) |
C12—C13 | 1.354 (5) | Ag1—O1 | 2.721 (3) |
C12—N4 | 1.370 (4) | ||
C6—C1—C2 | 119.9 (3) | N2—C15—C16 | 112.3 (3) |
C6—C1—S1 | 119.4 (3) | N2—C15—H15A | 109.1 |
C2—C1—S1 | 120.7 (2) | C16—C15—H15A | 109.1 |
N1—C2—C3 | 119.5 (3) | N2—C15—H15B | 109.1 |
N1—C2—C1 | 121.8 (3) | C16—C15—H15B | 109.1 |
C3—C2—C1 | 118.6 (3) | H15A—C15—H15B | 107.9 |
C4—C3—C2 | 119.1 (3) | C17—C16—C15 | 114.7 (3) |
C4—C3—C8 | 120.3 (3) | C17—C16—H16A | 108.6 |
C2—C3—C8 | 120.5 (3) | C15—C16—H16A | 108.6 |
C5—C4—C3 | 122.7 (3) | C17—C16—H16B | 108.6 |
C5—C4—H4 | 118.6 | C15—C16—H16B | 108.6 |
C3—C4—H4 | 118.6 | H16A—C16—H16B | 107.6 |
C6—C5—C4 | 117.7 (3) | C16—C17—C18 | 114.1 (3) |
C6—C5—C7 | 121.8 (4) | C16—C17—H17A | 108.7 |
C4—C5—C7 | 120.5 (4) | C18—C17—H17A | 108.7 |
C5—C6—C1 | 122.0 (3) | C16—C17—H17B | 108.7 |
C5—C6—H6 | 119.0 | C18—C17—H17B | 108.7 |
C1—C6—H6 | 119.0 | H17A—C17—H17B | 107.6 |
C5—C7—H7A | 109.5 | N5—C18—C17 | 111.2 (3) |
C5—C7—H7B | 109.5 | N5—C18—H18A | 109.4 |
H7A—C7—H7B | 109.5 | C17—C18—H18A | 109.4 |
C5—C7—H7C | 109.5 | N5—C18—H18B | 109.4 |
H7A—C7—H7C | 109.5 | C17—C18—H18B | 109.4 |
H7B—C7—H7C | 109.5 | H18A—C18—H18B | 108.0 |
C3—C8—H8A | 109.5 | C2—N1—H1A | 115 (3) |
C3—C8—H8B | 109.5 | C2—N1—H1B | 115 (2) |
H8A—C8—H8B | 109.5 | H1A—N1—H1B | 113 (4) |
C3—C8—H8C | 109.5 | C11—N2—C10 | 105.7 (3) |
H8A—C8—H8C | 109.5 | C11—N2—C15 | 126.3 (3) |
H8B—C8—H8C | 109.5 | C10—N2—C15 | 127.9 (3) |
C10—C9—N3 | 109.0 (3) | C11—N3—C9 | 105.8 (3) |
C10—C9—H9A | 125.5 | C11—N3—Ag1ii | 123.2 (2) |
N3—C9—H9A | 125.5 | C9—N3—Ag1ii | 130.8 (3) |
C9—C10—N2 | 107.5 (3) | C14—N4—C12 | 105.5 (3) |
C9—C10—H10A | 126.3 | C14—N4—Ag1 | 125.7 (2) |
N2—C10—H10A | 126.3 | C12—N4—Ag1 | 128.5 (3) |
N3—C11—N2 | 112.1 (3) | C14—N5—C13 | 107.1 (3) |
N3—C11—H11A | 124.0 | C14—N5—C18 | 126.5 (3) |
N2—C11—H11A | 124.0 | C13—N5—C18 | 126.3 (3) |
C13—C12—N4 | 109.1 (3) | O3—S1—O2 | 113.33 (17) |
C13—C12—H12 | 125.4 | O3—S1—O1 | 113.01 (17) |
N4—C12—H12 | 125.4 | O2—S1—O1 | 111.77 (17) |
C12—C13—N5 | 106.8 (3) | O3—S1—C1 | 105.46 (15) |
C12—C13—H13 | 126.6 | O2—S1—C1 | 106.71 (16) |
N5—C13—H13 | 126.6 | O1—S1—C1 | 105.84 (14) |
N4—C14—N5 | 111.5 (3) | N4—Ag1—O1 | 104.81 (10) |
N4—C14—H14 | 124.3 | O1—Ag1—N3i | 83.28 (10) |
N5—C14—H14 | 124.3 | N4—Ag1—N3i | 169.75 (12) |
C6—C1—C2—N1 | 176.8 (3) | C16—C15—N2—C11 | 64.0 (5) |
S1—C1—C2—N1 | −2.6 (4) | C16—C15—N2—C10 | −112.3 (4) |
C6—C1—C2—C3 | −0.3 (4) | N2—C11—N3—C9 | 0.2 (4) |
S1—C1—C2—C3 | −179.7 (2) | N2—C11—N3—Ag1ii | −176.2 (2) |
N1—C2—C3—C4 | −178.0 (3) | C10—C9—N3—C11 | −0.2 (4) |
C1—C2—C3—C4 | −0.8 (4) | C10—C9—N3—Ag1ii | 175.7 (3) |
N1—C2—C3—C8 | 2.0 (5) | N5—C14—N4—C12 | −0.2 (4) |
C1—C2—C3—C8 | 179.2 (3) | N5—C14—N4—Ag1 | 174.7 (2) |
C2—C3—C4—C5 | 1.0 (5) | C13—C12—N4—C14 | 0.4 (4) |
C8—C3—C4—C5 | −179.1 (3) | C13—C12—N4—Ag1 | −174.2 (3) |
C3—C4—C5—C6 | 0.0 (5) | N4—C14—N5—C13 | −0.1 (4) |
C3—C4—C5—C7 | −179.4 (3) | N4—C14—N5—C18 | −177.3 (3) |
C4—C5—C6—C1 | −1.2 (5) | C12—C13—N5—C14 | 0.4 (4) |
C7—C5—C6—C1 | 178.2 (3) | C12—C13—N5—C18 | 177.6 (3) |
C2—C1—C6—C5 | 1.3 (5) | C17—C18—N5—C14 | 121.1 (4) |
S1—C1—C6—C5 | −179.2 (2) | C17—C18—N5—C13 | −55.5 (5) |
N3—C9—C10—N2 | 0.2 (4) | C6—C1—S1—O3 | 129.0 (3) |
N4—C12—C13—N5 | −0.5 (4) | C2—C1—S1—O3 | −51.5 (3) |
N2—C15—C16—C17 | 59.2 (5) | C6—C1—S1—O2 | 8.2 (3) |
C15—C16—C17—C18 | −175.8 (3) | C2—C1—S1—O2 | −172.3 (2) |
C16—C17—C18—N5 | −57.1 (5) | C6—C1—S1—O1 | −111.0 (3) |
N3—C11—N2—C10 | 0.0 (4) | C2—C1—S1—O1 | 68.5 (3) |
N3—C11—N2—C15 | −177.0 (3) | C14—N4—Ag1—N3i | −5.9 (8) |
C9—C10—N2—C11 | −0.1 (4) | C12—N4—Ag1—N3i | 167.8 (6) |
C9—C10—N2—C15 | 176.8 (3) |
Symmetry codes: (i) x+1, −y+1/2, z−1/2; (ii) x−1, −y+1/2, z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O3 | 0.83 (4) | 2.34 (4) | 2.985 (5) | 136 (3) |
N1—H1B···O3iii | 0.92 (4) | 2.40 (4) | 3.252 (4) | 154 (3) |
Symmetry code: (iii) −x+2, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | [Ag(C8H10NO3S)(C10H14N4)] |
Mr | 498.35 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 292 |
a, b, c (Å) | 8.6632 (17), 17.239 (3), 13.789 (3) |
β (°) | 93.11 (3) |
V (Å3) | 2056.3 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.11 |
Crystal size (mm) | 0.31 × 0.27 × 0.24 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.703, 0.764 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 17540, 4617, 2695 |
Rint | 0.050 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.100, 0.98 |
No. of reflections | 4617 |
No. of parameters | 263 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.71, −0.69 |
Computer programs: PROCESS-AUTO (Rigaku, 1998), PROCESS-AUTO, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Sheldrick, 1990), SHELXL97.
Ag1—N4 | 2.101 (3) | Ag1—O1 | 2.721 (3) |
Ag1—N3i | 2.112 (3) | ||
N4—Ag1—O1 | 104.81 (10) | N4—Ag1—N3i | 169.75 (12) |
O1—Ag1—N3i | 83.28 (10) |
Symmetry code: (i) x+1, −y+1/2, z−1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O3 | 0.83 (4) | 2.34 (4) | 2.985 (5) | 136 (3) |
N1—H1B···O3ii | 0.92 (4) | 2.40 (4) | 3.252 (4) | 154 (3) |
Symmetry code: (ii) −x+2, −y, −z. |
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Recently, intense interest has been focused on silver(I) sulfonates due to their interesting structures and properties (May & Shimizu, 2005). Based on previous reports, the structure motif of most silver(I) sulfonates observed is a two-dimensional layer, which is similar to that of metal phosphonates (Sun et al., 2004). So far, some silver(I) sulfonate compounds modified by nitrogen-based ligands that display different structure motifs depending upon the presence of secondary ligands have been reported (You et al., 2004). However, the information on silver sulfonate coordination polymers are not yet well understood, especially, investigations of silver(I) sulfonates with neutral ligands are rather insufficient. We selected 2-amino-3,5-dimethylbenzenesulfonic acid (HL) as a sulfonate ligand and 1,1'-(1,4-butanediyl)-bis(imidazole) (bbi) as a secondary ligand, generating a new chain coordination polymer, [Ag(L)(bbi)], (I), which is reported here.
In compound (I), each AgI cation is three-coordinated by two N atoms from two different bbi ligands, and one sulfonate O atom from one L anion in a distorted trigonal-planar geometry (Fig. 1, Table 1). As shown in Fig. 2, each bbi moiety acts as a bidentate ligand that binds two AgI atoms, thus forming a one-dimensional chain. The L anions are attached on both sides of the chain through the Ag—O bonds. Moreover, N—H···O hydrogen bonds (Table 2) link the chains together, reinforcing the crystal cohesion of (I).