Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680704963X/sj2368sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680704963X/sj2368Isup2.hkl |
CCDC reference: 667156
An aqueous solution (15 ml) of 2-amino-3,5-dimethylbenzenesulfonic acid (1 mmol) was added to solid Ag2CO3 (0.5 mmol) and stirred for several minutes until no further CO2 was given off. 1-(3-(1H-imidazol-1-yl)methyl)benzyl)-1H-imidazole (1 mmol) was then added and a precipitate was formed. The precipitate was dissolved in ammonium hydroxide. Colorless crystals of (I) were obtained by evaporation of this solution for several days at room temperature.
H atoms bound to N atoms were located in a difference map and refined freely, with Uiso(H) = 1.2Ueq(N). H atoms bonded to C atoms were positioned geometrically with and refined as riding, with d(C—H) = 0.93 Å, Uiso = 1.2Ueq(C) for aromatic 0.97 Å, Uiso = 1.2Ueq(C) for CH2 and 0.96 Å, Uiso = 1.5Ueq(C) for CH3 atoms.
Sulfonates are generally perceived to be weaker ligands with low coordinating ability (Cote & Shimizu, 2003). Some silver(I) sulfonate compounds, modified by secondary nitrogen-based ligands, have been documented (Li et al., 2006). In most of these silver(I) sulfonate complexes, the sulfonate ligand acts solely as a counter-anion with no coordination to the AgI centre. Herein, we present a new sulfonate coordination polymer, namely [Ag(IBI)].L (I), where IBI = 1,2-bis((1H-imidazol-1-yl)methyl)benzene and HL = 2-amino-3,5-dimethylbenzenesulfonic acid.
In (I) the AgI cation is coordinated by N atoms from two different IBI ligands in a linear coordination geometry (Fig. 1). The Ag—N (IBI) distance in (I), Table 1, is similar to that in several related compounds (Li et al., 2006). The IBI ligand bridges two neighboring AgI atoms, forming a polymeric chain structure (Fig. 2). Notably, the L- ligand does not coordinate to the AgI center, acting only as a counter-anion and forming an intramolecular N—H···O hydrogen bond, Table 2.
For information on sulfonates as ligands, see Cote & Shimizu (2003). For related structures of silver sulfonates, see Li et al. (2006).
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).
[Ag(C14H14N2)](C8H10NO3S) | F(000) = 1112 |
Mr = 546.39 | Dx = 1.614 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 15895 reflections |
a = 10.683 (2) Å | θ = 3.0–27.5° |
b = 13.987 (3) Å | µ = 1.02 mm−1 |
c = 15.385 (3) Å | T = 293 K |
β = 102.07 (3)° | Block, colourless |
V = 2248.1 (8) Å3 | 0.27 × 0.21 × 0.19 mm |
Z = 4 |
Rigaku R-AXIS RAPID diffractometer | 5122 independent reflections |
Radiation source: rotating anode | 3779 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
Detector resolution: 10.0 pixels mm-1 | θmax = 27.5°, θmin = 3.1° |
ω scans | h = −12→13 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −18→18 |
Tmin = 0.755, Tmax = 0.824 | l = −19→19 |
20972 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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.147 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0791P)2 + 1.8517P] where P = (Fo2 + 2Fc2)/3 |
5122 reflections | (Δ/σ)max = 0.001 |
295 parameters | Δρmax = 1.69 e Å−3 |
3 restraints | Δρmin = −1.08 e Å−3 |
[Ag(C14H14N2)](C8H10NO3S) | V = 2248.1 (8) Å3 |
Mr = 546.39 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.683 (2) Å | µ = 1.02 mm−1 |
b = 13.987 (3) Å | T = 293 K |
c = 15.385 (3) Å | 0.27 × 0.21 × 0.19 mm |
β = 102.07 (3)° |
Rigaku R-AXIS RAPID diffractometer | 5122 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 3779 reflections with I > 2σ(I) |
Tmin = 0.755, Tmax = 0.824 | Rint = 0.034 |
20972 measured reflections |
R[F2 > 2σ(F2)] = 0.050 | 3 restraints |
wR(F2) = 0.147 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | Δρmax = 1.69 e Å−3 |
5122 reflections | Δρmin = −1.08 e Å−3 |
295 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 | ||
Ag1 | 0.80506 (3) | 0.22447 (2) | 0.46567 (3) | 0.05751 (16) | |
C1 | 0.7721 (4) | 0.4262 (3) | 0.7408 (2) | 0.0417 (8) | |
C2 | 0.6586 (4) | 0.4087 (3) | 0.7712 (3) | 0.0485 (10) | |
C3 | 0.5829 (4) | 0.4850 (4) | 0.7852 (3) | 0.0558 (11) | |
C4 | 0.6187 (5) | 0.5765 (3) | 0.7683 (3) | 0.0577 (11) | |
H4 | 0.5666 | 0.6271 | 0.7776 | 0.069* | |
C5 | 0.7290 (5) | 0.5963 (3) | 0.7381 (3) | 0.0521 (10) | |
C6 | 0.8072 (4) | 0.5209 (3) | 0.7249 (2) | 0.0462 (9) | |
H6 | 0.8827 | 0.5327 | 0.7056 | 0.055* | |
C7 | 0.4636 (6) | 0.4682 (5) | 0.8230 (5) | 0.0911 (19) | |
H7A | 0.4524 | 0.4008 | 0.8305 | 0.137* | |
H7B | 0.3901 | 0.4935 | 0.7828 | 0.137* | |
H7C | 0.4733 | 0.4996 | 0.8795 | 0.137* | |
C8 | 0.7649 (7) | 0.6982 (4) | 0.7215 (4) | 0.0848 (19) | |
H8A | 0.7003 | 0.7408 | 0.7339 | 0.127* | |
H8B | 0.7715 | 0.7052 | 0.6606 | 0.127* | |
H8C | 0.8457 | 0.7134 | 0.7596 | 0.127* | |
C12 | 0.8000 (5) | 0.4069 (3) | 0.3505 (3) | 0.0607 (12) | |
H12 | 0.7853 | 0.3707 | 0.2986 | 0.073* | |
C13 | 0.8194 (5) | 0.5016 (3) | 0.3547 (3) | 0.0602 (12) | |
H13 | 0.8214 | 0.5424 | 0.3073 | 0.072* | |
C14 | 0.8266 (4) | 0.4461 (3) | 0.4867 (3) | 0.0416 (8) | |
H14 | 0.8346 | 0.4433 | 0.5480 | 0.050* | |
C15 | 0.7291 (3) | 0.6783 (2) | 0.4694 (2) | 0.0359 (7) | |
C16 | 0.7329 (3) | 0.7772 (2) | 0.4811 (2) | 0.0328 (7) | |
C17 | 0.8609 (3) | 0.8280 (2) | 0.4959 (3) | 0.0367 (8) | |
H17A | 0.9213 | 0.7942 | 0.5413 | 0.044* | |
H17B | 0.8928 | 0.8257 | 0.4414 | 0.044* | |
C18 | 0.6192 (4) | 0.8265 (3) | 0.4773 (3) | 0.0445 (9) | |
H18 | 0.6211 | 0.8924 | 0.4857 | 0.053* | |
C19 | 0.5030 (4) | 0.7791 (3) | 0.4613 (4) | 0.0589 (12) | |
H19 | 0.4275 | 0.8132 | 0.4584 | 0.071* | |
C20 | 0.4992 (4) | 0.6823 (4) | 0.4497 (4) | 0.0634 (13) | |
H20 | 0.4211 | 0.6505 | 0.4390 | 0.076* | |
C21 | 0.6116 (4) | 0.6316 (3) | 0.4540 (3) | 0.0537 (10) | |
H21 | 0.6085 | 0.5656 | 0.4465 | 0.064* | |
C22 | 0.8532 (4) | 0.6233 (2) | 0.4755 (3) | 0.0425 (8) | |
H22A | 0.9071 | 0.6578 | 0.4426 | 0.051* | |
H22B | 0.8978 | 0.6209 | 0.5372 | 0.051* | |
N1 | 0.8051 (3) | 0.3716 (2) | 0.4339 (2) | 0.0429 (7) | |
N3 | 0.8356 (3) | 0.5266 (2) | 0.4413 (2) | 0.0388 (7) | |
N5 | 0.6217 (5) | 0.3171 (3) | 0.7929 (4) | 0.0778 (13) | |
O1 | 0.9699 (4) | 0.3667 (3) | 0.6837 (2) | 0.0685 (9) | |
O2 | 0.7907 (4) | 0.2586 (3) | 0.6756 (3) | 0.0724 (10) | |
O3 | 0.9261 (3) | 0.2952 (2) | 0.8160 (2) | 0.0543 (7) | |
S1 | 0.87311 (11) | 0.32912 (7) | 0.72741 (6) | 0.0452 (2) | |
N4 | 0.8549 (3) | 0.92730 (19) | 0.52284 (19) | 0.0332 (6) | |
C11 | 0.8364 (4) | 1.0041 (3) | 0.4692 (2) | 0.0370 (8) | |
H11 | 0.8298 | 1.0020 | 0.4080 | 0.044* | |
N2 | 0.8289 (3) | 1.0823 (2) | 0.5148 (2) | 0.0401 (7) | |
C9 | 0.8436 (4) | 1.0544 (3) | 0.6015 (3) | 0.0468 (9) | |
H9 | 0.8426 | 1.0951 | 0.6492 | 0.056* | |
C10 | 0.8597 (4) | 0.9588 (3) | 0.6074 (3) | 0.0455 (9) | |
H10 | 0.8717 | 0.9219 | 0.6587 | 0.055* | |
HN1 | 0.569 (3) | 0.2884 (16) | 0.819 (3) | 0.068* | |
HN2 | 0.642 (6) | 0.265 (2) | 0.769 (4) | 0.068* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ag1 | 0.0623 (3) | 0.02041 (17) | 0.0961 (3) | 0.00368 (12) | 0.0308 (2) | 0.01127 (14) |
C1 | 0.057 (2) | 0.0355 (19) | 0.0313 (17) | 0.0008 (16) | 0.0051 (15) | −0.0009 (15) |
C2 | 0.062 (3) | 0.041 (2) | 0.040 (2) | −0.0128 (18) | 0.0033 (17) | 0.0023 (17) |
C3 | 0.052 (3) | 0.068 (3) | 0.047 (2) | 0.000 (2) | 0.0098 (18) | 0.001 (2) |
C4 | 0.072 (3) | 0.049 (2) | 0.051 (2) | 0.019 (2) | 0.011 (2) | 0.003 (2) |
C5 | 0.082 (3) | 0.035 (2) | 0.040 (2) | 0.0051 (19) | 0.013 (2) | 0.0043 (17) |
C6 | 0.065 (3) | 0.040 (2) | 0.0344 (19) | −0.0027 (18) | 0.0128 (17) | 0.0016 (16) |
C7 | 0.067 (4) | 0.103 (5) | 0.111 (5) | 0.000 (3) | 0.036 (3) | 0.012 (4) |
C8 | 0.148 (6) | 0.036 (2) | 0.075 (4) | −0.002 (3) | 0.032 (4) | 0.008 (2) |
C12 | 0.105 (4) | 0.033 (2) | 0.047 (2) | −0.007 (2) | 0.023 (2) | −0.0101 (19) |
C13 | 0.106 (4) | 0.032 (2) | 0.045 (2) | −0.005 (2) | 0.023 (2) | 0.0028 (18) |
C14 | 0.057 (2) | 0.0232 (17) | 0.045 (2) | 0.0030 (14) | 0.0111 (17) | 0.0020 (15) |
C15 | 0.0398 (19) | 0.0262 (16) | 0.0424 (19) | −0.0011 (13) | 0.0102 (15) | −0.0016 (14) |
C16 | 0.0402 (19) | 0.0254 (16) | 0.0337 (17) | 0.0001 (13) | 0.0100 (13) | 0.0006 (13) |
C17 | 0.0408 (19) | 0.0198 (15) | 0.050 (2) | 0.0014 (13) | 0.0106 (15) | −0.0044 (14) |
C18 | 0.044 (2) | 0.0316 (18) | 0.060 (2) | 0.0057 (15) | 0.0156 (18) | −0.0015 (17) |
C19 | 0.036 (2) | 0.061 (3) | 0.082 (3) | 0.0062 (19) | 0.017 (2) | −0.004 (2) |
C20 | 0.038 (2) | 0.062 (3) | 0.091 (4) | −0.012 (2) | 0.014 (2) | −0.007 (3) |
C21 | 0.048 (2) | 0.036 (2) | 0.078 (3) | −0.0099 (17) | 0.014 (2) | −0.008 (2) |
C22 | 0.046 (2) | 0.0205 (16) | 0.061 (2) | 0.0001 (14) | 0.0115 (17) | −0.0042 (16) |
N1 | 0.059 (2) | 0.0200 (14) | 0.0521 (18) | 0.0001 (13) | 0.0167 (15) | −0.0022 (13) |
N3 | 0.0522 (19) | 0.0200 (14) | 0.0448 (17) | 0.0013 (12) | 0.0116 (14) | −0.0011 (12) |
N5 | 0.075 (3) | 0.056 (3) | 0.106 (4) | −0.015 (2) | 0.025 (3) | 0.004 (3) |
O1 | 0.093 (3) | 0.059 (2) | 0.064 (2) | 0.0174 (18) | 0.0403 (18) | 0.0161 (16) |
O2 | 0.079 (2) | 0.0484 (18) | 0.078 (2) | 0.0095 (17) | −0.0085 (18) | −0.0262 (17) |
O3 | 0.0555 (18) | 0.0563 (18) | 0.0488 (16) | 0.0018 (14) | 0.0056 (13) | 0.0192 (14) |
S1 | 0.0616 (6) | 0.0342 (5) | 0.0385 (5) | 0.0043 (4) | 0.0073 (4) | 0.0014 (4) |
N4 | 0.0432 (16) | 0.0206 (13) | 0.0367 (15) | −0.0002 (11) | 0.0105 (12) | −0.0020 (11) |
C11 | 0.048 (2) | 0.0249 (16) | 0.0382 (18) | 0.0007 (14) | 0.0098 (15) | 0.0016 (14) |
N2 | 0.0519 (19) | 0.0213 (14) | 0.0497 (18) | −0.0009 (12) | 0.0168 (14) | 0.0003 (13) |
C9 | 0.068 (3) | 0.0287 (18) | 0.046 (2) | 0.0009 (17) | 0.0170 (19) | −0.0112 (16) |
C10 | 0.066 (3) | 0.0343 (19) | 0.038 (2) | 0.0037 (17) | 0.0163 (18) | 0.0013 (16) |
Ag1—N1 | 2.115 (3) | C15—C22 | 1.519 (5) |
Ag1—N2i | 2.124 (3) | C16—C18 | 1.387 (5) |
C1—C2 | 1.410 (6) | C16—C17 | 1.515 (5) |
C1—C6 | 1.412 (6) | C17—N4 | 1.454 (4) |
C1—S1 | 1.773 (4) | C17—H17A | 0.9700 |
C2—C3 | 1.383 (6) | C17—H17B | 0.9700 |
C2—N5 | 1.401 (6) | C18—C19 | 1.383 (6) |
C3—C4 | 1.376 (7) | C18—H18 | 0.9300 |
C3—C7 | 1.525 (7) | C19—C20 | 1.365 (7) |
C4—C5 | 1.383 (7) | C19—H19 | 0.9300 |
C4—H4 | 0.9300 | C20—C21 | 1.385 (7) |
C5—C6 | 1.386 (6) | C20—H20 | 0.9300 |
C5—C8 | 1.512 (7) | C21—H21 | 0.9300 |
C6—H6 | 0.9300 | C22—N3 | 1.448 (4) |
C7—H7A | 0.9600 | C22—H22A | 0.9700 |
C7—H7B | 0.9600 | C22—H22B | 0.9700 |
C7—H7C | 0.9600 | N5—HN1 | 0.858 (10) |
C8—H8A | 0.9600 | N5—HN2 | 0.863 (10) |
C8—H8B | 0.9600 | O1—S1 | 1.445 (3) |
C8—H8C | 0.9600 | O2—S1 | 1.446 (4) |
C12—C13 | 1.341 (6) | O3—S1 | 1.443 (3) |
C12—N1 | 1.365 (6) | N4—C11 | 1.343 (5) |
C12—H12 | 0.9300 | N4—C10 | 1.365 (5) |
C13—N3 | 1.353 (5) | C11—N2 | 1.311 (5) |
C13—H13 | 0.9300 | C11—H11 | 0.9300 |
C14—N1 | 1.312 (5) | N2—C9 | 1.368 (5) |
C14—N3 | 1.339 (5) | N2—Ag1ii | 2.124 (3) |
C14—H14 | 0.9300 | C9—C10 | 1.348 (5) |
C15—C21 | 1.390 (5) | C9—H9 | 0.9300 |
C15—C16 | 1.396 (5) | C10—H10 | 0.9300 |
N1—Ag1—N2i | 170.93 (13) | C16—C17—H17B | 108.9 |
C2—C1—C6 | 119.9 (4) | H17A—C17—H17B | 107.7 |
C2—C1—S1 | 119.4 (3) | C19—C18—C16 | 121.0 (4) |
C6—C1—S1 | 120.6 (3) | C19—C18—H18 | 119.5 |
C3—C2—N5 | 117.7 (4) | C16—C18—H18 | 119.5 |
C3—C2—C1 | 119.3 (4) | C20—C19—C18 | 120.0 (4) |
N5—C2—C1 | 122.9 (4) | C20—C19—H19 | 120.0 |
C4—C3—C2 | 119.6 (4) | C18—C19—H19 | 120.0 |
C4—C3—C7 | 120.2 (5) | C19—C20—C21 | 120.0 (4) |
C2—C3—C7 | 120.2 (5) | C19—C20—H20 | 120.0 |
C3—C4—C5 | 122.7 (4) | C21—C20—H20 | 120.0 |
C3—C4—H4 | 118.6 | C20—C21—C15 | 120.7 (4) |
C5—C4—H4 | 118.6 | C20—C21—H21 | 119.6 |
C4—C5—C6 | 118.6 (4) | C15—C21—H21 | 119.6 |
C4—C5—C8 | 120.6 (5) | N3—C22—C15 | 113.8 (3) |
C6—C5—C8 | 120.7 (5) | N3—C22—H22A | 108.8 |
C5—C6—C1 | 119.9 (4) | C15—C22—H22A | 108.8 |
C5—C6—H6 | 120.1 | N3—C22—H22B | 108.8 |
C1—C6—H6 | 120.1 | C15—C22—H22B | 108.8 |
C3—C7—H7A | 109.5 | H22A—C22—H22B | 107.7 |
C3—C7—H7B | 109.5 | C14—N1—C12 | 105.2 (3) |
H7A—C7—H7B | 109.5 | C14—N1—Ag1 | 129.7 (3) |
C3—C7—H7C | 109.5 | C12—N1—Ag1 | 124.5 (3) |
H7A—C7—H7C | 109.5 | C14—N3—C13 | 106.7 (3) |
H7B—C7—H7C | 109.5 | C14—N3—C22 | 127.9 (3) |
C5—C8—H8A | 109.5 | C13—N3—C22 | 125.3 (3) |
C5—C8—H8B | 109.5 | C2—N5—HN1 | 141.7 (17) |
H8A—C8—H8B | 109.5 | C2—N5—HN2 | 124 (4) |
C5—C8—H8C | 109.5 | HN1—N5—HN2 | 93 (4) |
H8A—C8—H8C | 109.5 | O3—S1—O1 | 112.4 (2) |
H8B—C8—H8C | 109.5 | O3—S1—O2 | 111.7 (2) |
C13—C12—N1 | 109.6 (4) | O1—S1—O2 | 113.9 (2) |
C13—C12—H12 | 125.2 | O3—S1—C1 | 105.71 (19) |
N1—C12—H12 | 125.2 | O1—S1—C1 | 106.67 (19) |
C12—C13—N3 | 106.9 (4) | O2—S1—C1 | 105.7 (2) |
C12—C13—H13 | 126.6 | C11—N4—C10 | 107.4 (3) |
N3—C13—H13 | 126.6 | C11—N4—C17 | 126.7 (3) |
N1—C14—N3 | 111.6 (3) | C10—N4—C17 | 125.8 (3) |
N1—C14—H14 | 124.2 | N2—C11—N4 | 110.9 (3) |
N3—C14—H14 | 124.2 | N2—C11—H11 | 124.6 |
C21—C15—C16 | 119.2 (3) | N4—C11—H11 | 124.6 |
C21—C15—C22 | 121.2 (3) | C11—N2—C9 | 106.0 (3) |
C16—C15—C22 | 119.5 (3) | C11—N2—Ag1ii | 127.4 (3) |
C18—C16—C15 | 119.1 (3) | C9—N2—Ag1ii | 126.5 (2) |
C18—C16—C17 | 121.9 (3) | C10—C9—N2 | 109.6 (3) |
C15—C16—C17 | 119.0 (3) | C10—C9—H9 | 125.2 |
N4—C17—C16 | 113.5 (3) | N2—C9—H9 | 125.2 |
N4—C17—H17A | 108.9 | C9—C10—N4 | 106.1 (3) |
C16—C17—H17A | 108.9 | C9—C10—H10 | 126.9 |
N4—C17—H17B | 108.9 | N4—C10—H10 | 126.9 |
C6—C1—C2—C3 | 0.0 (6) | C16—C15—C22—N3 | −165.8 (3) |
S1—C1—C2—C3 | 177.2 (3) | N3—C14—N1—C12 | −0.1 (5) |
C6—C1—C2—N5 | −176.4 (4) | N3—C14—N1—Ag1 | 171.3 (3) |
S1—C1—C2—N5 | 0.8 (6) | C13—C12—N1—C14 | 0.4 (6) |
N5—C2—C3—C4 | 177.3 (5) | C13—C12—N1—Ag1 | −171.5 (4) |
C1—C2—C3—C4 | 0.7 (6) | N2i—Ag1—N1—C14 | −35.2 (10) |
N5—C2—C3—C7 | 0.0 (7) | N2i—Ag1—N1—C12 | 134.7 (7) |
C1—C2—C3—C7 | −176.6 (4) | N1—C14—N3—C13 | −0.3 (5) |
C2—C3—C4—C5 | −0.4 (7) | N1—C14—N3—C22 | 177.1 (4) |
C7—C3—C4—C5 | 176.9 (5) | C12—C13—N3—C14 | 0.6 (6) |
C3—C4—C5—C6 | −0.5 (7) | C12—C13—N3—C22 | −177.0 (4) |
C3—C4—C5—C8 | −179.3 (5) | C15—C22—N3—C14 | −94.2 (5) |
C4—C5—C6—C1 | 1.2 (6) | C15—C22—N3—C13 | 82.8 (5) |
C8—C5—C6—C1 | 179.9 (4) | C2—C1—S1—O3 | −68.3 (3) |
C2—C1—C6—C5 | −0.9 (6) | C6—C1—S1—O3 | 108.9 (3) |
S1—C1—C6—C5 | −178.1 (3) | C2—C1—S1—O1 | 171.8 (3) |
N1—C12—C13—N3 | −0.6 (6) | C6—C1—S1—O1 | −11.0 (4) |
C21—C15—C16—C18 | 0.2 (5) | C2—C1—S1—O2 | 50.2 (4) |
C22—C15—C16—C18 | −178.6 (4) | C6—C1—S1—O2 | −132.5 (4) |
C21—C15—C16—C17 | −178.7 (4) | C16—C17—N4—C11 | −92.5 (4) |
C22—C15—C16—C17 | 2.5 (5) | C16—C17—N4—C10 | 83.4 (5) |
C18—C16—C17—N4 | 11.5 (5) | C10—N4—C11—N2 | −0.2 (4) |
C15—C16—C17—N4 | −169.6 (3) | C17—N4—C11—N2 | 176.3 (3) |
C15—C16—C18—C19 | −0.7 (6) | N4—C11—N2—C9 | 0.2 (4) |
C17—C16—C18—C19 | 178.2 (4) | N4—C11—N2—Ag1ii | 178.3 (2) |
C16—C18—C19—C20 | 0.6 (7) | C11—N2—C9—C10 | −0.1 (5) |
C18—C19—C20—C21 | 0.0 (8) | Ag1ii—N2—C9—C10 | −178.3 (3) |
C19—C20—C21—C15 | −0.5 (8) | N2—C9—C10—N4 | 0.0 (5) |
C16—C15—C21—C20 | 0.4 (7) | C11—N4—C10—C9 | 0.1 (5) |
C22—C15—C21—C20 | 179.2 (4) | C17—N4—C10—C9 | −176.4 (4) |
C21—C15—C22—N3 | 15.4 (6) |
Symmetry codes: (i) x, y−1, z; (ii) x, y+1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N5—HN2···O2 | 0.86 (1) | 2.36 (5) | 2.924 (7) | 123 (5) |
Experimental details
Crystal data | |
Chemical formula | [Ag(C14H14N2)](C8H10NO3S) |
Mr | 546.39 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 10.683 (2), 13.987 (3), 15.385 (3) |
β (°) | 102.07 (3) |
V (Å3) | 2248.1 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.02 |
Crystal size (mm) | 0.27 × 0.21 × 0.19 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.755, 0.824 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 20972, 5122, 3779 |
Rint | 0.034 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.050, 0.147, 1.08 |
No. of reflections | 5122 |
No. of parameters | 295 |
No. of restraints | 3 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 1.69, −1.08 |
Computer programs: PROCESS-AUTO (Rigaku, 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Sheldrick, 1990).
Ag1—N1 | 2.115 (3) | Ag1—N2i | 2.124 (3) |
N1—Ag1—N2i | 170.93 (13) |
Symmetry code: (i) x, y−1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N5—HN2···O2 | 0.863 (10) | 2.36 (5) | 2.924 (7) | 123 (5) |
Sulfonates are generally perceived to be weaker ligands with low coordinating ability (Cote & Shimizu, 2003). Some silver(I) sulfonate compounds, modified by secondary nitrogen-based ligands, have been documented (Li et al., 2006). In most of these silver(I) sulfonate complexes, the sulfonate ligand acts solely as a counter-anion with no coordination to the AgI centre. Herein, we present a new sulfonate coordination polymer, namely [Ag(IBI)].L (I), where IBI = 1,2-bis((1H-imidazol-1-yl)methyl)benzene and HL = 2-amino-3,5-dimethylbenzenesulfonic acid.
In (I) the AgI cation is coordinated by N atoms from two different IBI ligands in a linear coordination geometry (Fig. 1). The Ag—N (IBI) distance in (I), Table 1, is similar to that in several related compounds (Li et al., 2006). The IBI ligand bridges two neighboring AgI atoms, forming a polymeric chain structure (Fig. 2). Notably, the L- ligand does not coordinate to the AgI center, acting only as a counter-anion and forming an intramolecular N—H···O hydrogen bond, Table 2.