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A one-dimensional AgI coordination complex, catena-poly[[silver(I)-[mu]-{2-[2-(pyridin-4-yl)-1H-benzimidazol-1-ylmethyl]phenol-[kappa]2N2:N3}] perchlorate monohydrate], {[Ag(C19H15N3O)]ClO4·H2O}n, was synthesized by the reaction of 2-[2-(pyridin-4-yl)-1H-benzimidazol-1-ylmethyl]phenol (L) with silver perchlorate. In the complex, the L ligands are arranged alternately and link AgI 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 [pi]-[pi] 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270113005817/wq3027sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270113005817/wq3027Isup2.hkl
Contains datablock I

CCDC reference: 879705

Computing details top

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)-1H-benzimidazol-1-ylmethyl]phenol-κ2N2:N3}] perchlorate monohydrate] top
Crystal data top
[Ag(C19H15N3O)]ClO4·H2OF(000) = 1056
Mr = 526.68Dx = 1.748 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 5048 reflections
a = 9.739 (3) Åθ = 2.3–28.2°
b = 21.260 (7) ŵ = 1.18 mm1
c = 9.952 (3) ÅT = 296 K
β = 103.851 (3)°Block, colourless
V = 2000.8 (11) Å30.23 × 0.21 × 0.16 mm
Z = 4
Data collection top
Bruker APEXII CCD area-detector
diffractometer
3712 independent reflections
Radiation source: fine-focus sealed tube3023 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
φ and ω scansθmax = 25.5°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 119
Tmin = 0.772, Tmax = 0.833k = 2525
10711 measured reflectionsl = 1112
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098H 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 parametersΔρmax = 0.62 e Å3
3 restraintsΔρmin = 0.68 e Å3
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
xyzUiso*/Ueq
Ag10.11957 (4)0.828815 (14)0.37908 (4)0.04760 (13)
C10.2473 (4)1.01422 (15)0.5315 (4)0.0282 (7)
C20.2306 (4)1.07915 (17)0.5172 (4)0.0349 (8)
H20.28861.10680.57770.042*
C30.1241 (4)1.10039 (19)0.4095 (4)0.0439 (10)
H30.10951.14340.39690.053*
C40.0378 (4)1.05856 (19)0.3187 (4)0.0423 (10)
H40.03321.07460.24720.051*
C50.0544 (4)0.99477 (18)0.3315 (4)0.0361 (9)
H50.00320.96720.27020.043*
C60.1614 (4)0.97299 (16)0.4406 (4)0.0286 (8)
C70.3071 (4)0.91684 (15)0.5924 (4)0.0268 (7)
C80.3816 (4)0.86186 (16)0.6642 (4)0.0286 (8)
C90.5260 (4)0.85504 (17)0.6840 (4)0.0363 (9)
H90.57960.88680.65720.044*
C100.5902 (4)0.80058 (18)0.7443 (4)0.0414 (9)
H100.68740.79610.75610.050*
C110.3788 (5)0.76084 (18)0.7658 (5)0.0450 (10)
H110.32740.72850.79340.054*
C120.3076 (4)0.81321 (17)0.7063 (5)0.0394 (9)
H120.21010.81600.69420.047*
C130.4355 (4)1.00207 (17)0.7557 (4)0.0354 (8)
H13A0.49611.03430.73180.042*
H13B0.49540.96820.80190.042*
C140.3540 (4)1.02929 (17)0.8527 (4)0.0338 (8)
C150.3435 (5)1.09382 (19)0.8697 (4)0.0493 (11)
H150.39051.12090.82250.059*
C160.2652 (6)1.1182 (2)0.9550 (5)0.0660 (15)
H160.25861.16150.96490.079*
C170.1972 (6)1.0787 (2)1.0249 (5)0.0615 (13)
H170.14221.09541.08080.074*
C180.2084 (5)1.0143 (2)1.0143 (4)0.0482 (10)
H180.16400.98771.06490.058*
C190.2866 (4)0.98963 (18)0.9273 (4)0.0368 (9)
Cl10.48617 (13)0.76977 (6)0.34110 (14)0.0599 (3)
N10.3401 (3)0.97766 (13)0.6279 (3)0.0270 (6)
N20.2016 (3)0.91201 (13)0.4816 (3)0.0285 (6)
N30.5181 (4)0.75419 (14)0.7861 (4)0.0393 (8)
O10.3008 (3)0.92688 (13)0.9095 (3)0.0482 (7)
H10.27220.90770.96890.072*
O20.4204 (6)0.8299 (3)0.3398 (6)0.136 (2)
O30.6273 (4)0.7772 (2)0.4112 (5)0.0911 (14)
O40.4202 (7)0.7306 (4)0.4127 (7)0.204 (4)
O50.4690 (7)0.7535 (3)0.2017 (5)0.129 (2)
O60.1963 (7)0.8518 (2)0.0830 (5)0.0896 (13)
H1W0.133 (6)0.830 (3)0.032 (8)0.18 (5)*
H2W0.272 (5)0.836 (3)0.131 (9)0.17 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ag10.0518 (2)0.03009 (17)0.0568 (2)0.01082 (14)0.00479 (15)0.01380 (14)
C10.0305 (19)0.0242 (17)0.0293 (18)0.0004 (15)0.0059 (15)0.0016 (14)
C20.040 (2)0.0241 (17)0.040 (2)0.0033 (16)0.0093 (18)0.0014 (15)
C30.051 (3)0.032 (2)0.052 (3)0.0102 (18)0.019 (2)0.0128 (18)
C40.040 (2)0.048 (2)0.037 (2)0.0094 (19)0.0057 (18)0.0140 (18)
C50.032 (2)0.043 (2)0.0312 (19)0.0031 (17)0.0038 (16)0.0002 (16)
C60.033 (2)0.0268 (17)0.0265 (18)0.0000 (15)0.0078 (15)0.0023 (14)
C70.0264 (18)0.0231 (16)0.0324 (18)0.0013 (14)0.0102 (15)0.0015 (14)
C80.0299 (19)0.0253 (17)0.0309 (18)0.0034 (14)0.0078 (15)0.0006 (14)
C90.035 (2)0.0284 (18)0.048 (2)0.0023 (16)0.0134 (18)0.0056 (16)
C100.033 (2)0.036 (2)0.054 (3)0.0060 (17)0.0102 (19)0.0031 (18)
C110.046 (3)0.0297 (19)0.063 (3)0.0021 (18)0.020 (2)0.0111 (19)
C120.029 (2)0.0287 (19)0.063 (3)0.0019 (16)0.0163 (19)0.0063 (18)
C130.032 (2)0.0344 (19)0.035 (2)0.0082 (16)0.0021 (16)0.0031 (16)
C140.034 (2)0.0335 (19)0.0284 (19)0.0004 (16)0.0025 (16)0.0037 (15)
C150.073 (3)0.033 (2)0.039 (2)0.006 (2)0.008 (2)0.0057 (17)
C160.105 (4)0.043 (3)0.050 (3)0.011 (3)0.019 (3)0.014 (2)
C170.076 (4)0.065 (3)0.045 (3)0.017 (3)0.018 (2)0.011 (2)
C180.049 (3)0.058 (3)0.037 (2)0.001 (2)0.010 (2)0.0002 (19)
C190.036 (2)0.038 (2)0.030 (2)0.0013 (17)0.0040 (16)0.0030 (16)
Cl10.0478 (7)0.0585 (7)0.0742 (8)0.0142 (6)0.0164 (6)0.0028 (6)
N10.0289 (16)0.0227 (14)0.0278 (15)0.0018 (12)0.0035 (13)0.0018 (11)
N20.0279 (16)0.0259 (14)0.0309 (16)0.0001 (12)0.0053 (13)0.0049 (12)
N30.0394 (19)0.0304 (16)0.047 (2)0.0085 (14)0.0088 (16)0.0065 (14)
O10.063 (2)0.0341 (15)0.0473 (17)0.0035 (14)0.0128 (15)0.0020 (13)
O20.147 (5)0.157 (5)0.104 (4)0.096 (4)0.030 (3)0.002 (3)
O30.044 (2)0.093 (3)0.137 (4)0.012 (2)0.024 (2)0.028 (3)
O40.149 (5)0.274 (8)0.149 (5)0.160 (6)0.041 (4)0.108 (6)
O50.177 (5)0.118 (4)0.088 (3)0.012 (4)0.020 (3)0.045 (3)
O60.109 (4)0.079 (3)0.078 (3)0.021 (3)0.018 (3)0.021 (2)
Geometric parameters (Å, º) top
Ag1—N22.102 (3)C12—H120.9300
Ag1—N3i2.124 (3)C13—N11.479 (4)
C1—C61.387 (5)C13—C141.505 (5)
C1—N11.388 (4)C13—H13A0.9700
C1—C21.393 (5)C13—H13B0.9700
C2—C31.377 (5)C14—C191.388 (5)
C2—H20.9300C14—C151.389 (5)
C3—C41.396 (6)C15—C161.372 (7)
C3—H30.9300C15—H150.9300
C4—C51.368 (6)C16—C171.359 (7)
C4—H40.9300C16—H160.9300
C5—C61.392 (5)C17—C181.379 (7)
C5—H50.9300C17—H170.9300
C6—N21.387 (4)C18—C191.386 (6)
C7—N21.319 (4)C18—H180.9300
C7—N11.358 (4)C19—O11.357 (5)
C7—C81.468 (5)Cl1—O41.354 (5)
C8—C91.380 (5)Cl1—O31.393 (4)
C8—C121.381 (5)Cl1—O51.400 (5)
C9—C101.382 (5)Cl1—O51.400 (5)
C9—H90.9300Cl1—O21.428 (5)
C10—N31.334 (5)Cl1—O21.428 (5)
C10—H100.9300N3—Ag1ii2.124 (3)
C11—N31.331 (5)O1—H10.8200
C11—C121.369 (5)O6—H1W0.842 (10)
C11—H110.9300O6—H2W0.843 (10)
N2—Ag1—N3i173.76 (12)C19—C14—C15118.5 (4)
C6—C1—N1106.8 (3)C19—C14—C13120.0 (3)
C6—C1—C2121.5 (3)C15—C14—C13121.6 (4)
N1—C1—C2131.8 (3)C16—C15—C14121.1 (4)
C3—C2—C1116.9 (4)C16—C15—H15119.4
C3—C2—H2121.6C14—C15—H15119.4
C1—C2—H2121.6C17—C16—C15119.6 (4)
C2—C3—C4121.3 (4)C17—C16—H16120.2
C2—C3—H3119.4C15—C16—H16120.2
C4—C3—H3119.4C16—C17—C18121.1 (5)
C5—C4—C3122.1 (4)C16—C17—H17119.4
C5—C4—H4118.9C18—C17—H17119.4
C3—C4—H4118.9C17—C18—C19119.3 (4)
C4—C5—C6116.9 (4)C17—C18—H18120.4
C4—C5—H5121.6C19—C18—H18120.4
C6—C5—H5121.6O1—C19—C18122.8 (4)
N2—C6—C1108.3 (3)O1—C19—C14116.8 (4)
N2—C6—C5130.3 (3)C18—C19—C14120.4 (4)
C1—C6—C5121.4 (3)O4—Cl1—O3110.0 (3)
N2—C7—N1112.3 (3)O4—Cl1—O5114.2 (4)
N2—C7—C8122.7 (3)O3—Cl1—O5113.2 (3)
N1—C7—C8125.0 (3)O4—Cl1—O5114.2 (4)
C9—C8—C12117.7 (3)O3—Cl1—O5113.2 (3)
C9—C8—C7121.4 (3)O4—Cl1—O2106.7 (5)
C12—C8—C7120.7 (3)O3—Cl1—O2106.9 (3)
C8—C9—C10119.3 (4)O5—Cl1—O2105.3 (3)
C8—C9—H9120.3O5—Cl1—O2105.3 (3)
C10—C9—H9120.3O4—Cl1—O2106.7 (5)
N3—C10—C9122.5 (4)O3—Cl1—O2106.9 (3)
N3—C10—H10118.8O5—Cl1—O2105.3 (3)
C9—C10—H10118.8O5—Cl1—O2105.3 (3)
N3—C11—C12123.0 (4)C7—N1—C1106.2 (3)
N3—C11—H11118.5C7—N1—C13128.2 (3)
C12—C11—H11118.5C1—N1—C13124.7 (3)
C11—C12—C8119.6 (4)C7—N2—C6106.4 (3)
C11—C12—H12120.2C7—N2—Ag1126.9 (2)
C8—C12—H12120.2C6—N2—Ag1126.6 (2)
N1—C13—C14111.5 (3)C11—N3—C10117.9 (3)
N1—C13—H13A109.3C11—N3—Ag1ii120.4 (3)
C14—C13—H13A109.3C10—N3—Ag1ii121.7 (3)
N1—C13—H13B109.3C19—O1—H1109.5
C14—C13—H13B109.3H1W—O6—H2W122 (2)
H13A—C13—H13B108.0
C6—C1—C2—C30.5 (6)C17—C18—C19—C140.6 (6)
N1—C1—C2—C3178.7 (4)C15—C14—C19—O1179.1 (4)
C1—C2—C3—C40.3 (6)C13—C14—C19—O11.1 (5)
C2—C3—C4—C50.2 (6)C15—C14—C19—C181.4 (6)
C3—C4—C5—C60.4 (6)C13—C14—C19—C18178.4 (4)
N1—C1—C6—N20.1 (4)N2—C7—N1—C10.2 (4)
C2—C1—C6—N2179.3 (3)C8—C7—N1—C1178.2 (3)
N1—C1—C6—C5179.1 (3)N2—C7—N1—C13169.8 (3)
C2—C1—C6—C50.3 (6)C8—C7—N1—C1312.2 (6)
C4—C5—C6—N2178.5 (4)C6—C1—N1—C70.2 (4)
C4—C5—C6—C10.2 (6)C2—C1—N1—C7179.1 (4)
N2—C7—C8—C9123.2 (4)C6—C1—N1—C13170.2 (3)
N1—C7—C8—C954.6 (5)C2—C1—N1—C139.1 (6)
N2—C7—C8—C1252.6 (5)C14—C13—N1—C7104.0 (4)
N1—C7—C8—C12129.6 (4)C14—C13—N1—C163.8 (4)
C12—C8—C9—C100.1 (6)N1—C7—N2—C60.1 (4)
C7—C8—C9—C10175.9 (3)C8—C7—N2—C6178.1 (3)
C8—C9—C10—N30.9 (6)N1—C7—N2—Ag1176.1 (2)
N3—C11—C12—C80.2 (7)C8—C7—N2—Ag12.0 (5)
C9—C8—C12—C110.3 (6)C5—C6—N2—C7178.9 (4)
C7—C8—C12—C11176.2 (4)C1—C6—N2—Ag1176.2 (2)
N1—C13—C14—C1974.4 (4)C5—C6—N2—Ag14.9 (6)
N1—C13—C14—C15105.4 (4)N3i—Ag1—N2—C7103.2 (11)
C19—C14—C15—C161.9 (6)N3i—Ag1—N2—C681.3 (12)
C13—C14—C15—C16177.9 (4)C12—C11—N3—C100.9 (6)
C14—C15—C16—C170.4 (8)C12—C11—N3—Ag1ii179.9 (3)
C15—C16—C17—C181.6 (8)C9—C10—N3—C111.3 (6)
C16—C17—C18—C192.1 (7)C9—C10—N3—Ag1ii179.7 (3)
C17—C18—C19—O1178.9 (4)
Symmetry codes: (i) x1/2, y+3/2, z1/2; (ii) x+1/2, y+3/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O6—H1W···O3i0.84 (1)2.57 (6)3.217 (7)135 (7)
O6—H1W···O4i0.84 (1)2.48 (2)3.316 (9)169 (9)
O1—H1···O6iii0.821.912.721 (5)170
O6—H2W···O20.84 (1)2.23 (5)2.973 (8)146 (9)
O6—H2W···O50.84 (1)2.57 (4)3.363 (9)157 (7)
Symmetry codes: (i) x1/2, y+3/2, z1/2; (iii) x, y, z+1.
 

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