A one-dimensional Ag
I coordination complex,
catena-poly[[silver(I)-
-{2-[2-(pyridin-4-yl)-1
H-benzimidazol-1-ylmethyl]phenol-
2N2:
N3}] perchlorate monohydrate], {[Ag(C
19H
15N
3O)]ClO
4·H
2O}
n, was synthesized by the reaction of 2-[2-(pyridin-4-yl)-1
H-benzimidazol-1-ylmethyl]phenol (
L) with silver perchlorate. In the complex, the
L ligands are arranged alternately and link Ag
I cations through one benzimidazole N atom and the N atom of the pyridine ring, leading to an extended zigzag chain structure. In addition, the one-dimensional chains are extended into a three-dimensional supramolecular architecture
via O-H
O hydrogen-bond interactions and
-
stacking interactions. The complex exhibits photoluminescence in acetonitrile solution, with an emission maximum at 390 nm, and investigation of the thermal stability reveals that the network structure is stable up to 650 K.
Supporting information
CCDC reference: 879705
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
catena-Poly[[silver(I)-µ-{2-[2-(pyridin-4-yl)-1
H-benzimidazol-1-ylmethyl]phenol-
κ2N2:
N3}] perchlorate
monohydrate]
top
Crystal data top
[Ag(C19H15N3O)]ClO4·H2O | F(000) = 1056 |
Mr = 526.68 | Dx = 1.748 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 5048 reflections |
a = 9.739 (3) Å | θ = 2.3–28.2° |
b = 21.260 (7) Å | µ = 1.18 mm−1 |
c = 9.952 (3) Å | T = 296 K |
β = 103.851 (3)° | Block, colourless |
V = 2000.8 (11) Å3 | 0.23 × 0.21 × 0.16 mm |
Z = 4 | |
Data collection top
Bruker APEXII CCD area-detector diffractometer | 3712 independent reflections |
Radiation source: fine-focus sealed tube | 3023 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
φ and ω scans | θmax = 25.5°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −11→9 |
Tmin = 0.772, Tmax = 0.833 | k = −25→25 |
10711 measured reflections | l = −11→12 |
Refinement top
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: inferred from neighbouring sites |
wR(F2) = 0.098 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.12 | w = 1/[σ2(Fo2) + (0.0386P)2 + 2.8471P] where P = (Fo2 + 2Fc2)/3 |
3712 reflections | (Δ/σ)max = 0.002 |
280 parameters | Δρmax = 0.62 e Å−3 |
3 restraints | Δρmin = −0.68 e Å−3 |
Special details top
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 (Å2) top | x | y | z | Uiso*/Ueq | |
Ag1 | 0.11957 (4) | 0.828815 (14) | 0.37908 (4) | 0.04760 (13) | |
C1 | 0.2473 (4) | 1.01422 (15) | 0.5315 (4) | 0.0282 (7) | |
C2 | 0.2306 (4) | 1.07915 (17) | 0.5172 (4) | 0.0349 (8) | |
H2 | 0.2886 | 1.1068 | 0.5777 | 0.042* | |
C3 | 0.1241 (4) | 1.10039 (19) | 0.4095 (4) | 0.0439 (10) | |
H3 | 0.1095 | 1.1434 | 0.3969 | 0.053* | |
C4 | 0.0378 (4) | 1.05856 (19) | 0.3187 (4) | 0.0423 (10) | |
H4 | −0.0332 | 1.0746 | 0.2472 | 0.051* | |
C5 | 0.0544 (4) | 0.99477 (18) | 0.3315 (4) | 0.0361 (9) | |
H5 | −0.0032 | 0.9672 | 0.2702 | 0.043* | |
C6 | 0.1614 (4) | 0.97299 (16) | 0.4406 (4) | 0.0286 (8) | |
C7 | 0.3071 (4) | 0.91684 (15) | 0.5924 (4) | 0.0268 (7) | |
C8 | 0.3816 (4) | 0.86186 (16) | 0.6642 (4) | 0.0286 (8) | |
C9 | 0.5260 (4) | 0.85504 (17) | 0.6840 (4) | 0.0363 (9) | |
H9 | 0.5796 | 0.8868 | 0.6572 | 0.044* | |
C10 | 0.5902 (4) | 0.80058 (18) | 0.7443 (4) | 0.0414 (9) | |
H10 | 0.6874 | 0.7961 | 0.7561 | 0.050* | |
C11 | 0.3788 (5) | 0.76084 (18) | 0.7658 (5) | 0.0450 (10) | |
H11 | 0.3274 | 0.7285 | 0.7934 | 0.054* | |
C12 | 0.3076 (4) | 0.81321 (17) | 0.7063 (5) | 0.0394 (9) | |
H12 | 0.2101 | 0.8160 | 0.6942 | 0.047* | |
C13 | 0.4355 (4) | 1.00207 (17) | 0.7557 (4) | 0.0354 (8) | |
H13A | 0.4961 | 1.0343 | 0.7318 | 0.042* | |
H13B | 0.4954 | 0.9682 | 0.8019 | 0.042* | |
C14 | 0.3540 (4) | 1.02929 (17) | 0.8527 (4) | 0.0338 (8) | |
C15 | 0.3435 (5) | 1.09382 (19) | 0.8697 (4) | 0.0493 (11) | |
H15 | 0.3905 | 1.1209 | 0.8225 | 0.059* | |
C16 | 0.2652 (6) | 1.1182 (2) | 0.9550 (5) | 0.0660 (15) | |
H16 | 0.2586 | 1.1615 | 0.9649 | 0.079* | |
C17 | 0.1972 (6) | 1.0787 (2) | 1.0249 (5) | 0.0615 (13) | |
H17 | 0.1422 | 1.0954 | 1.0808 | 0.074* | |
C18 | 0.2084 (5) | 1.0143 (2) | 1.0143 (4) | 0.0482 (10) | |
H18 | 0.1640 | 0.9877 | 1.0649 | 0.058* | |
C19 | 0.2866 (4) | 0.98963 (18) | 0.9273 (4) | 0.0368 (9) | |
Cl1 | 0.48617 (13) | 0.76977 (6) | 0.34110 (14) | 0.0599 (3) | |
N1 | 0.3401 (3) | 0.97766 (13) | 0.6279 (3) | 0.0270 (6) | |
N2 | 0.2016 (3) | 0.91201 (13) | 0.4816 (3) | 0.0285 (6) | |
N3 | 0.5181 (4) | 0.75419 (14) | 0.7861 (4) | 0.0393 (8) | |
O1 | 0.3008 (3) | 0.92688 (13) | 0.9095 (3) | 0.0482 (7) | |
H1 | 0.2722 | 0.9077 | 0.9689 | 0.072* | |
O2 | 0.4204 (6) | 0.8299 (3) | 0.3398 (6) | 0.136 (2) | |
O3 | 0.6273 (4) | 0.7772 (2) | 0.4112 (5) | 0.0911 (14) | |
O4 | 0.4202 (7) | 0.7306 (4) | 0.4127 (7) | 0.204 (4) | |
O5 | 0.4690 (7) | 0.7535 (3) | 0.2017 (5) | 0.129 (2) | |
O6 | 0.1963 (7) | 0.8518 (2) | 0.0830 (5) | 0.0896 (13) | |
H1W | 0.133 (6) | 0.830 (3) | 0.032 (8) | 0.18 (5)* | |
H2W | 0.272 (5) | 0.836 (3) | 0.131 (9) | 0.17 (5)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ag1 | 0.0518 (2) | 0.03009 (17) | 0.0568 (2) | −0.01082 (14) | 0.00479 (15) | −0.01380 (14) |
C1 | 0.0305 (19) | 0.0242 (17) | 0.0293 (18) | −0.0004 (15) | 0.0059 (15) | 0.0016 (14) |
C2 | 0.040 (2) | 0.0241 (17) | 0.040 (2) | −0.0033 (16) | 0.0093 (18) | 0.0014 (15) |
C3 | 0.051 (3) | 0.032 (2) | 0.052 (3) | 0.0102 (18) | 0.019 (2) | 0.0128 (18) |
C4 | 0.040 (2) | 0.048 (2) | 0.037 (2) | 0.0094 (19) | 0.0057 (18) | 0.0140 (18) |
C5 | 0.032 (2) | 0.043 (2) | 0.0312 (19) | 0.0031 (17) | 0.0038 (16) | −0.0002 (16) |
C6 | 0.033 (2) | 0.0268 (17) | 0.0265 (18) | 0.0000 (15) | 0.0078 (15) | 0.0023 (14) |
C7 | 0.0264 (18) | 0.0231 (16) | 0.0324 (18) | −0.0013 (14) | 0.0102 (15) | −0.0015 (14) |
C8 | 0.0299 (19) | 0.0253 (17) | 0.0309 (18) | 0.0034 (14) | 0.0078 (15) | −0.0006 (14) |
C9 | 0.035 (2) | 0.0284 (18) | 0.048 (2) | 0.0023 (16) | 0.0134 (18) | 0.0056 (16) |
C10 | 0.033 (2) | 0.036 (2) | 0.054 (3) | 0.0060 (17) | 0.0102 (19) | 0.0031 (18) |
C11 | 0.046 (3) | 0.0297 (19) | 0.063 (3) | 0.0021 (18) | 0.020 (2) | 0.0111 (19) |
C12 | 0.029 (2) | 0.0287 (19) | 0.063 (3) | 0.0019 (16) | 0.0163 (19) | 0.0063 (18) |
C13 | 0.032 (2) | 0.0344 (19) | 0.035 (2) | −0.0082 (16) | −0.0021 (16) | −0.0031 (16) |
C14 | 0.034 (2) | 0.0335 (19) | 0.0284 (19) | −0.0004 (16) | −0.0025 (16) | −0.0037 (15) |
C15 | 0.073 (3) | 0.033 (2) | 0.039 (2) | −0.006 (2) | 0.008 (2) | −0.0057 (17) |
C16 | 0.105 (4) | 0.043 (3) | 0.050 (3) | 0.011 (3) | 0.019 (3) | −0.014 (2) |
C17 | 0.076 (4) | 0.065 (3) | 0.045 (3) | 0.017 (3) | 0.018 (2) | −0.011 (2) |
C18 | 0.049 (3) | 0.058 (3) | 0.037 (2) | −0.001 (2) | 0.010 (2) | 0.0002 (19) |
C19 | 0.036 (2) | 0.038 (2) | 0.030 (2) | −0.0013 (17) | −0.0040 (16) | −0.0030 (16) |
Cl1 | 0.0478 (7) | 0.0585 (7) | 0.0742 (8) | −0.0142 (6) | 0.0164 (6) | −0.0028 (6) |
N1 | 0.0289 (16) | 0.0227 (14) | 0.0278 (15) | −0.0018 (12) | 0.0035 (13) | −0.0018 (11) |
N2 | 0.0279 (16) | 0.0259 (14) | 0.0309 (16) | −0.0001 (12) | 0.0053 (13) | −0.0049 (12) |
N3 | 0.0394 (19) | 0.0304 (16) | 0.047 (2) | 0.0085 (14) | 0.0088 (16) | 0.0065 (14) |
O1 | 0.063 (2) | 0.0341 (15) | 0.0473 (17) | −0.0035 (14) | 0.0128 (15) | 0.0020 (13) |
O2 | 0.147 (5) | 0.157 (5) | 0.104 (4) | 0.096 (4) | 0.030 (3) | 0.002 (3) |
O3 | 0.044 (2) | 0.093 (3) | 0.137 (4) | −0.012 (2) | 0.024 (2) | −0.028 (3) |
O4 | 0.149 (5) | 0.274 (8) | 0.149 (5) | −0.160 (6) | −0.041 (4) | 0.108 (6) |
O5 | 0.177 (5) | 0.118 (4) | 0.088 (3) | −0.012 (4) | 0.020 (3) | −0.045 (3) |
O6 | 0.109 (4) | 0.079 (3) | 0.078 (3) | −0.021 (3) | 0.018 (3) | 0.021 (2) |
Geometric parameters (Å, º) top
Ag1—N2 | 2.102 (3) | C12—H12 | 0.9300 |
Ag1—N3i | 2.124 (3) | C13—N1 | 1.479 (4) |
C1—C6 | 1.387 (5) | C13—C14 | 1.505 (5) |
C1—N1 | 1.388 (4) | C13—H13A | 0.9700 |
C1—C2 | 1.393 (5) | C13—H13B | 0.9700 |
C2—C3 | 1.377 (5) | C14—C19 | 1.388 (5) |
C2—H2 | 0.9300 | C14—C15 | 1.389 (5) |
C3—C4 | 1.396 (6) | C15—C16 | 1.372 (7) |
C3—H3 | 0.9300 | C15—H15 | 0.9300 |
C4—C5 | 1.368 (6) | C16—C17 | 1.359 (7) |
C4—H4 | 0.9300 | C16—H16 | 0.9300 |
C5—C6 | 1.392 (5) | C17—C18 | 1.379 (7) |
C5—H5 | 0.9300 | C17—H17 | 0.9300 |
C6—N2 | 1.387 (4) | C18—C19 | 1.386 (6) |
C7—N2 | 1.319 (4) | C18—H18 | 0.9300 |
C7—N1 | 1.358 (4) | C19—O1 | 1.357 (5) |
C7—C8 | 1.468 (5) | Cl1—O4 | 1.354 (5) |
C8—C9 | 1.380 (5) | Cl1—O3 | 1.393 (4) |
C8—C12 | 1.381 (5) | Cl1—O5 | 1.400 (5) |
C9—C10 | 1.382 (5) | Cl1—O5 | 1.400 (5) |
C9—H9 | 0.9300 | Cl1—O2 | 1.428 (5) |
C10—N3 | 1.334 (5) | Cl1—O2 | 1.428 (5) |
C10—H10 | 0.9300 | N3—Ag1ii | 2.124 (3) |
C11—N3 | 1.331 (5) | O1—H1 | 0.8200 |
C11—C12 | 1.369 (5) | O6—H1W | 0.842 (10) |
C11—H11 | 0.9300 | O6—H2W | 0.843 (10) |
| | | |
N2—Ag1—N3i | 173.76 (12) | C19—C14—C15 | 118.5 (4) |
C6—C1—N1 | 106.8 (3) | C19—C14—C13 | 120.0 (3) |
C6—C1—C2 | 121.5 (3) | C15—C14—C13 | 121.6 (4) |
N1—C1—C2 | 131.8 (3) | C16—C15—C14 | 121.1 (4) |
C3—C2—C1 | 116.9 (4) | C16—C15—H15 | 119.4 |
C3—C2—H2 | 121.6 | C14—C15—H15 | 119.4 |
C1—C2—H2 | 121.6 | C17—C16—C15 | 119.6 (4) |
C2—C3—C4 | 121.3 (4) | C17—C16—H16 | 120.2 |
C2—C3—H3 | 119.4 | C15—C16—H16 | 120.2 |
C4—C3—H3 | 119.4 | C16—C17—C18 | 121.1 (5) |
C5—C4—C3 | 122.1 (4) | C16—C17—H17 | 119.4 |
C5—C4—H4 | 118.9 | C18—C17—H17 | 119.4 |
C3—C4—H4 | 118.9 | C17—C18—C19 | 119.3 (4) |
C4—C5—C6 | 116.9 (4) | C17—C18—H18 | 120.4 |
C4—C5—H5 | 121.6 | C19—C18—H18 | 120.4 |
C6—C5—H5 | 121.6 | O1—C19—C18 | 122.8 (4) |
N2—C6—C1 | 108.3 (3) | O1—C19—C14 | 116.8 (4) |
N2—C6—C5 | 130.3 (3) | C18—C19—C14 | 120.4 (4) |
C1—C6—C5 | 121.4 (3) | O4—Cl1—O3 | 110.0 (3) |
N2—C7—N1 | 112.3 (3) | O4—Cl1—O5 | 114.2 (4) |
N2—C7—C8 | 122.7 (3) | O3—Cl1—O5 | 113.2 (3) |
N1—C7—C8 | 125.0 (3) | O4—Cl1—O5 | 114.2 (4) |
C9—C8—C12 | 117.7 (3) | O3—Cl1—O5 | 113.2 (3) |
C9—C8—C7 | 121.4 (3) | O4—Cl1—O2 | 106.7 (5) |
C12—C8—C7 | 120.7 (3) | O3—Cl1—O2 | 106.9 (3) |
C8—C9—C10 | 119.3 (4) | O5—Cl1—O2 | 105.3 (3) |
C8—C9—H9 | 120.3 | O5—Cl1—O2 | 105.3 (3) |
C10—C9—H9 | 120.3 | O4—Cl1—O2 | 106.7 (5) |
N3—C10—C9 | 122.5 (4) | O3—Cl1—O2 | 106.9 (3) |
N3—C10—H10 | 118.8 | O5—Cl1—O2 | 105.3 (3) |
C9—C10—H10 | 118.8 | O5—Cl1—O2 | 105.3 (3) |
N3—C11—C12 | 123.0 (4) | C7—N1—C1 | 106.2 (3) |
N3—C11—H11 | 118.5 | C7—N1—C13 | 128.2 (3) |
C12—C11—H11 | 118.5 | C1—N1—C13 | 124.7 (3) |
C11—C12—C8 | 119.6 (4) | C7—N2—C6 | 106.4 (3) |
C11—C12—H12 | 120.2 | C7—N2—Ag1 | 126.9 (2) |
C8—C12—H12 | 120.2 | C6—N2—Ag1 | 126.6 (2) |
N1—C13—C14 | 111.5 (3) | C11—N3—C10 | 117.9 (3) |
N1—C13—H13A | 109.3 | C11—N3—Ag1ii | 120.4 (3) |
C14—C13—H13A | 109.3 | C10—N3—Ag1ii | 121.7 (3) |
N1—C13—H13B | 109.3 | C19—O1—H1 | 109.5 |
C14—C13—H13B | 109.3 | H1W—O6—H2W | 122 (2) |
H13A—C13—H13B | 108.0 | | |
| | | |
C6—C1—C2—C3 | 0.5 (6) | C17—C18—C19—C14 | 0.6 (6) |
N1—C1—C2—C3 | −178.7 (4) | C15—C14—C19—O1 | −179.1 (4) |
C1—C2—C3—C4 | −0.3 (6) | C13—C14—C19—O1 | 1.1 (5) |
C2—C3—C4—C5 | −0.2 (6) | C15—C14—C19—C18 | 1.4 (6) |
C3—C4—C5—C6 | 0.4 (6) | C13—C14—C19—C18 | −178.4 (4) |
N1—C1—C6—N2 | 0.1 (4) | N2—C7—N1—C1 | 0.2 (4) |
C2—C1—C6—N2 | −179.3 (3) | C8—C7—N1—C1 | 178.2 (3) |
N1—C1—C6—C5 | 179.1 (3) | N2—C7—N1—C13 | 169.8 (3) |
C2—C1—C6—C5 | −0.3 (6) | C8—C7—N1—C13 | −12.2 (6) |
C4—C5—C6—N2 | 178.5 (4) | C6—C1—N1—C7 | −0.2 (4) |
C4—C5—C6—C1 | −0.2 (6) | C2—C1—N1—C7 | 179.1 (4) |
N2—C7—C8—C9 | 123.2 (4) | C6—C1—N1—C13 | −170.2 (3) |
N1—C7—C8—C9 | −54.6 (5) | C2—C1—N1—C13 | 9.1 (6) |
N2—C7—C8—C12 | −52.6 (5) | C14—C13—N1—C7 | −104.0 (4) |
N1—C7—C8—C12 | 129.6 (4) | C14—C13—N1—C1 | 63.8 (4) |
C12—C8—C9—C10 | 0.1 (6) | N1—C7—N2—C6 | −0.1 (4) |
C7—C8—C9—C10 | −175.9 (3) | C8—C7—N2—C6 | −178.1 (3) |
C8—C9—C10—N3 | −0.9 (6) | N1—C7—N2—Ag1 | 176.1 (2) |
N3—C11—C12—C8 | 0.2 (7) | C8—C7—N2—Ag1 | −2.0 (5) |
C9—C8—C12—C11 | 0.3 (6) | C5—C6—N2—C7 | −178.9 (4) |
C7—C8—C12—C11 | 176.2 (4) | C1—C6—N2—Ag1 | −176.2 (2) |
N1—C13—C14—C19 | 74.4 (4) | C5—C6—N2—Ag1 | 4.9 (6) |
N1—C13—C14—C15 | −105.4 (4) | N3i—Ag1—N2—C7 | 103.2 (11) |
C19—C14—C15—C16 | −1.9 (6) | N3i—Ag1—N2—C6 | −81.3 (12) |
C13—C14—C15—C16 | 177.9 (4) | C12—C11—N3—C10 | −0.9 (6) |
C14—C15—C16—C17 | 0.4 (8) | C12—C11—N3—Ag1ii | −179.9 (3) |
C15—C16—C17—C18 | 1.6 (8) | C9—C10—N3—C11 | 1.3 (6) |
C16—C17—C18—C19 | −2.1 (7) | C9—C10—N3—Ag1ii | −179.7 (3) |
C17—C18—C19—O1 | −178.9 (4) | | |
Symmetry codes: (i) x−1/2, −y+3/2, z−1/2; (ii) x+1/2, −y+3/2, z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O6—H1W···O3i | 0.84 (1) | 2.57 (6) | 3.217 (7) | 135 (7) |
O6—H1W···O4i | 0.84 (1) | 2.48 (2) | 3.316 (9) | 169 (9) |
O1—H1···O6iii | 0.82 | 1.91 | 2.721 (5) | 170 |
O6—H2W···O2 | 0.84 (1) | 2.23 (5) | 2.973 (8) | 146 (9) |
O6—H2W···O5 | 0.84 (1) | 2.57 (4) | 3.363 (9) | 157 (7) |
Symmetry codes: (i) x−1/2, −y+3/2, z−1/2; (iii) x, y, z+1. |