Download citation
Download citation
link to html
A novel ladder-type coordination polymer (CP), poly[(μ-4,4′-bi­pyridine-κ2N:N′){μ-4-[(4-carb­oxy­benz­yloxy)meth­yl]benzoato-κO}silver(I)](AgAg), [Ag(C16H13O5)(C10H8N2)]n or [Ag(HL)(4,4′-bpy)]n {H2L is 4,4′-[oxybis(methyl­ene)]di­benzoic acid and 4,4′-bpy is 4,4′-bi­pyridine}, was synthesized using hydro­thermal methods. The com­plex was characterized by IR spectroscopy, elemental analysis and single-crystal X-ray diffraction, and is a ladder-type CP which exhibits an obvious Ag—Ag interaction. The legs of the ladder are formed by parallel 4,4′-bipy ligands and silver ions, and the rungs are constructed by Ag—Ag interactions. A Hirshfeld surface analysis was carried out and is discussed in detail. The com­plex also displays favourable fluorescence properties.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229620011882/dg3009sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229620011882/dg3009Isup3.hkl
Contains datablock I

mol

MDL mol file https://doi.org/10.1107/S2053229620011882/dg3009Isup4.mol
Supplementary material

CCDC reference: 2025969

Computing details top

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXT2015 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Poly[(µ-4,4'-bipyridine-κ2N:N'){µ-4-[(4-carboxybenzyloxy)methyl]benzoato-κO}silver(I)](AgAg) top
Crystal data top
[Ag(C16H13O5)(C10H8N2)]Z = 2
Mr = 549.32F(000) = 556
Triclinic, P1Dx = 1.612 Mg m3
a = 7.9269 (6) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.3939 (8) ÅCell parameters from 2207 reflections
c = 13.6589 (8) Åθ = 3.7–21.0°
α = 78.610 (5)°µ = 0.93 mm1
β = 81.339 (6)°T = 289 K
γ = 70.031 (6)°Plate, colourless
V = 1132.01 (14) Å30.22 × 0.21 × 0.11 mm
Data collection top
Agilent SuperNova Single Source
diffractometer with an E detector
4035 independent reflections
Radiation source: SuperNova (Mo) X-ray Source2501 reflections with I > 2σ(I)
Detector resolution: 16.0233 pixels mm-1Rint = 0.073
ω scansθmax = 25.1°, θmin = 3.4°
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2014)
h = 99
Tmin = 0.429, Tmax = 0.871k = 1313
14148 measured reflectionsl = 1616
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051H-atom parameters constrained
wR(F2) = 0.115 w = 1/[σ2(Fo2) + (0.0304P)2 + 0.7458P]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
4035 reflectionsΔρmax = 0.55 e Å3
303 parametersΔρmin = 0.57 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. The diffraction data of 1 were collected on a SuperNova (Single source at offset, Eos) with graphite monochromated Mo-Ka radiation (λ = 0.71073 Å), using the ω scan mode in the range 3.35° θ 25.10°. The raw frame data were integrated with the CrysAlis PRO program. The structure 1 were solved by direct methods using SHELXT (Sheldrick, 2008, 2015) and refined by full-matrix least-squares on F2 using SHELXL2018 within the OLEX-2 GUI (Dolomanov, et al. 2009). An empirical absorption correction was applied with spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. All non-hydrogen atoms were refined anisotropically.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Ag10.32970 (6)0.44453 (4)0.51821 (4)0.0608 (2)
O31.3458 (5)1.1536 (4)0.8164 (3)0.0667 (12)
O41.1040 (5)1.3147 (4)0.7749 (4)0.0672 (12)
H41.17931.35080.75550.101*
O90.8298 (6)0.7584 (4)0.9504 (3)0.0701 (12)
O20.2698 (6)0.4736 (4)0.7553 (3)0.0665 (12)
N10.4973 (6)1.2490 (4)0.5112 (4)0.0486 (12)
C20.4494 (8)1.1724 (5)0.5962 (5)0.0626 (18)
H20.49531.20330.65620.075*
O10.5166 (6)0.4518 (4)0.6490 (3)0.0688 (13)
C50.2613 (7)0.9992 (5)0.5134 (4)0.0389 (13)
C130.6773 (8)0.5348 (5)0.7796 (4)0.0481 (15)
H130.75070.49850.72640.058*
C120.4989 (7)0.5410 (5)0.7932 (4)0.0405 (13)
C251.0642 (7)1.1175 (5)0.8342 (4)0.0420 (13)
C30.3356 (8)1.0498 (5)0.6004 (4)0.0569 (17)
H3A0.30811.00030.66230.068*
C200.8453 (8)0.9639 (5)0.8833 (4)0.0470 (14)
C40.3119 (8)1.0796 (5)0.4259 (4)0.0555 (17)
H4A0.26711.05140.36470.067*
C211.0303 (8)0.9131 (5)0.8847 (4)0.0578 (16)
H211.08260.82620.90220.069*
C261.1854 (8)1.1954 (6)0.8081 (4)0.0493 (15)
C110.4235 (9)0.4830 (5)0.7270 (5)0.0488 (15)
C241.1391 (8)0.9893 (5)0.8607 (4)0.0548 (16)
H241.26330.95340.86240.066*
C140.3926 (8)0.5997 (5)0.8701 (4)0.0497 (15)
H140.27120.60650.88010.060*
C230.8791 (7)1.1698 (5)0.8328 (4)0.0497 (15)
H230.82701.25670.81530.060*
C160.7486 (8)0.5810 (5)0.8427 (5)0.0579 (16)
H160.87020.57360.83280.069*
C170.6419 (9)0.6388 (5)0.9213 (4)0.0506 (15)
C220.7710 (7)1.0929 (5)0.8574 (4)0.0483 (15)
H220.64671.12890.85640.058*
C190.7263 (8)0.8831 (5)0.9132 (5)0.0580 (16)
H19A0.63320.91720.96440.070*
H19B0.66830.88280.85560.070*
C150.4634 (8)0.6489 (5)0.9332 (4)0.0569 (16)
H150.38860.68920.98420.068*
C10.4279 (8)1.2011 (5)0.4271 (4)0.0584 (17)
H10.45931.25210.36610.070*
C180.7241 (10)0.6800 (6)0.9958 (5)0.075 (2)
H18A0.62830.72541.04090.090*
H18B0.79930.60541.03560.090*
C60.1344 (9)0.8662 (5)0.5141 (6)0.0401 (13)0.677 (11)
C80.1265 (10)0.7734 (7)0.5979 (5)0.045 (3)0.677 (11)
H8A0.20390.79190.65520.054*0.677 (11)
C90.0031 (11)0.6529 (6)0.5961 (5)0.047 (3)0.677 (11)
H9A0.00220.59080.65220.057*0.677 (11)
N20.1125 (8)0.6252 (5)0.5105 (6)0.0433 (16)0.677 (11)
C100.1046 (10)0.7180 (7)0.4267 (5)0.041 (2)0.677 (11)
H10A0.18190.69950.36940.049*0.677 (11)
C70.0188 (11)0.8385 (6)0.4284 (5)0.044 (3)0.677 (11)
H7A0.02410.90070.37240.053*0.677 (11)
C6'0.133 (2)0.8703 (11)0.5145 (13)0.0401 (13)0.323 (11)
C8'0.071 (2)0.8059 (15)0.6064 (11)0.045 (3)0.323 (11)
H8'A0.10650.84580.66280.054*0.323 (11)
C9'0.044 (3)0.6817 (15)0.6141 (11)0.047 (3)0.323 (11)
H9'A0.08550.63860.67560.057*0.323 (11)
N2'0.097 (2)0.6221 (12)0.5298 (14)0.0433 (16)0.323 (11)
C10'0.035 (2)0.6865 (16)0.4379 (11)0.041 (2)0.323 (11)
H10B0.07070.64660.38150.049*0.323 (11)
C7'0.080 (2)0.8107 (15)0.4302 (11)0.044 (3)0.323 (11)
H7'A0.12130.85380.36870.053*0.323 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ag10.0548 (3)0.0338 (3)0.0852 (4)0.0053 (2)0.0155 (3)0.0179 (2)
O30.039 (3)0.075 (3)0.087 (3)0.020 (2)0.011 (2)0.008 (2)
O40.052 (3)0.056 (3)0.100 (4)0.027 (2)0.019 (3)0.001 (2)
O90.081 (3)0.054 (3)0.089 (3)0.037 (3)0.019 (3)0.007 (2)
O20.067 (3)0.061 (3)0.087 (3)0.036 (2)0.016 (3)0.014 (2)
N10.048 (3)0.030 (3)0.063 (3)0.002 (2)0.009 (3)0.012 (2)
C20.082 (5)0.039 (4)0.056 (4)0.003 (3)0.001 (4)0.015 (3)
O10.074 (3)0.067 (3)0.067 (3)0.013 (2)0.009 (3)0.031 (2)
C50.043 (3)0.032 (3)0.038 (3)0.008 (3)0.006 (3)0.004 (2)
C130.047 (4)0.050 (4)0.048 (4)0.016 (3)0.005 (3)0.016 (3)
C120.046 (4)0.028 (3)0.045 (3)0.009 (3)0.006 (3)0.005 (2)
C250.037 (3)0.047 (4)0.049 (3)0.016 (3)0.009 (3)0.014 (3)
C30.076 (5)0.042 (4)0.038 (3)0.002 (3)0.005 (3)0.008 (3)
C200.050 (4)0.049 (4)0.051 (4)0.026 (3)0.003 (3)0.011 (3)
C40.071 (4)0.042 (4)0.041 (4)0.004 (3)0.009 (3)0.016 (3)
C210.051 (4)0.039 (4)0.084 (5)0.012 (3)0.010 (3)0.012 (3)
C260.050 (4)0.055 (4)0.050 (4)0.023 (3)0.006 (3)0.013 (3)
C110.059 (4)0.029 (3)0.053 (4)0.007 (3)0.016 (3)0.002 (3)
C240.041 (4)0.048 (4)0.075 (4)0.006 (3)0.010 (3)0.018 (3)
C140.042 (4)0.043 (3)0.065 (4)0.013 (3)0.004 (3)0.010 (3)
C230.043 (4)0.045 (4)0.059 (4)0.012 (3)0.011 (3)0.006 (3)
C160.049 (4)0.057 (4)0.075 (5)0.026 (3)0.003 (3)0.013 (3)
C170.070 (5)0.041 (4)0.052 (4)0.030 (3)0.014 (3)0.005 (3)
C220.039 (3)0.042 (4)0.063 (4)0.010 (3)0.013 (3)0.006 (3)
C190.058 (4)0.054 (4)0.069 (4)0.027 (3)0.004 (3)0.011 (3)
C150.064 (4)0.051 (4)0.058 (4)0.018 (3)0.001 (3)0.020 (3)
C10.078 (5)0.040 (4)0.046 (4)0.004 (3)0.013 (3)0.002 (3)
C180.108 (6)0.071 (5)0.064 (4)0.050 (4)0.021 (4)0.003 (4)
C60.033 (3)0.033 (3)0.047 (3)0.001 (2)0.004 (3)0.010 (3)
C80.051 (6)0.023 (5)0.053 (4)0.007 (4)0.006 (4)0.005 (4)
C90.060 (7)0.036 (5)0.040 (5)0.009 (4)0.004 (4)0.004 (4)
N20.048 (3)0.036 (3)0.042 (4)0.004 (2)0.008 (3)0.009 (3)
C100.037 (6)0.041 (5)0.044 (4)0.003 (4)0.004 (4)0.019 (4)
C70.057 (7)0.027 (5)0.050 (4)0.007 (4)0.011 (4)0.016 (3)
C6'0.033 (3)0.033 (3)0.047 (3)0.001 (2)0.004 (3)0.010 (3)
C8'0.051 (6)0.023 (5)0.053 (4)0.007 (4)0.006 (4)0.005 (4)
C9'0.060 (7)0.036 (5)0.040 (5)0.009 (4)0.004 (4)0.004 (4)
N2'0.048 (3)0.036 (3)0.042 (4)0.004 (2)0.008 (3)0.009 (3)
C10'0.037 (6)0.041 (5)0.044 (4)0.003 (4)0.004 (4)0.019 (4)
C7'0.057 (7)0.027 (5)0.050 (4)0.007 (4)0.011 (4)0.016 (3)
Geometric parameters (Å, º) top
Ag1—N22.182 (6)C24—H240.9300
Ag1—N1i2.194 (4)C14—C151.387 (7)
Ag1—N2'2.238 (13)C14—H140.9300
Ag1—O12.517 (4)C23—C221.388 (7)
Ag1—Ag1ii3.2883 (10)C23—H230.9300
O3—C261.211 (6)C16—C171.388 (7)
O4—C261.310 (6)C16—H160.9300
O4—H40.8200C17—C151.367 (8)
O9—C191.412 (6)C17—C181.510 (7)
O9—C181.422 (7)C22—H220.9300
O2—C111.256 (7)C19—H19A0.9700
N1—C21.326 (7)C19—H19B0.9700
N1—C11.332 (6)C15—H150.9300
N1—Ag1iii2.193 (4)C1—H10.9300
C2—C31.375 (7)C18—H18A0.9700
C2—H20.9300C18—H18B0.9700
O1—C111.241 (6)C6—C81.3900
C5—C41.375 (7)C6—C71.3900
C5—C31.385 (7)C8—C91.3900
C5—C6'1.472 (13)C8—H8A0.9300
C5—C61.505 (7)C9—N21.3900
C13—C161.366 (7)C9—H9A0.9300
C13—C121.378 (7)N2—C101.3900
C13—H130.9300C10—C71.3900
C12—C141.373 (7)C10—H10A0.9300
C12—C111.510 (7)C7—H7A0.9300
C25—C241.372 (7)C6'—C8'1.3900
C25—C231.384 (7)C6'—C7'1.3900
C25—C261.481 (7)C8'—C9'1.3900
C3—H3A0.9300C8'—H8'A0.9300
C20—C221.377 (7)C9'—N2'1.3900
C20—C211.382 (7)C9'—H9'A0.9300
C20—C191.494 (7)N2'—C10'1.3900
C4—C11.377 (7)C10'—C7'1.3900
C4—H4A0.9300C10'—H10B0.9300
C21—C241.385 (7)C7'—H7'A0.9300
C21—H210.9300
N2—Ag1—N1i166.4 (2)C17—C16—H16119.6
N1i—Ag1—N2'165.3 (4)C15—C17—C16118.0 (5)
N2—Ag1—O1104.10 (19)C15—C17—C18121.1 (6)
N1i—Ag1—O188.46 (15)C16—C17—C18120.7 (6)
N2'—Ag1—O1100.8 (4)C20—C22—C23120.9 (5)
N2—Ag1—Ag1ii97.87 (17)C20—C22—H22119.6
N1i—Ag1—Ag1ii93.78 (12)C23—C22—H22119.6
N2'—Ag1—Ag1ii100.9 (4)O9—C19—C20109.7 (5)
O1—Ag1—Ag1ii52.96 (11)O9—C19—H19A109.7
C26—O4—H4109.5C20—C19—H19A109.7
C19—O9—C18113.6 (5)O9—C19—H19B109.7
C2—N1—C1116.2 (5)C20—C19—H19B109.7
C2—N1—Ag1iii118.7 (4)H19A—C19—H19B108.2
C1—N1—Ag1iii125.0 (4)C17—C15—C14120.8 (5)
N1—C2—C3123.6 (5)C17—C15—H15119.6
N1—C2—H2118.2C14—C15—H15119.6
C3—C2—H2118.2N1—C1—C4123.2 (5)
C11—O1—Ag1112.2 (4)N1—C1—H1118.4
C4—C5—C3115.1 (5)C4—C1—H1118.4
C4—C5—C6'122.5 (8)O9—C18—C17113.5 (5)
C3—C5—C6'122.4 (8)O9—C18—H18A108.9
C4—C5—C6122.2 (5)C17—C18—H18A108.9
C3—C5—C6122.7 (5)O9—C18—H18B108.9
C16—C13—C12121.3 (5)C17—C18—H18B108.9
C16—C13—H13119.3H18A—C18—H18B107.7
C12—C13—H13119.3C8—C6—C7120.0
C14—C12—C13117.8 (5)C8—C6—C5122.0 (5)
C14—C12—C11121.1 (5)C7—C6—C5117.9 (5)
C13—C12—C11121.1 (5)C6—C8—C9120.0
C24—C25—C23119.3 (5)C6—C8—H8A120.0
C24—C25—C26118.4 (5)C9—C8—H8A120.0
C23—C25—C26122.2 (5)N2—C9—C8120.0
C2—C3—C5120.8 (5)N2—C9—H9A120.0
C2—C3—H3A119.6C8—C9—H9A120.0
C5—C3—H3A119.6C10—N2—C9120.0
C22—C20—C21118.3 (5)C10—N2—Ag1120.7 (4)
C22—C20—C19120.1 (5)C9—N2—Ag1118.7 (4)
C21—C20—C19121.5 (5)N2—C10—C7120.0
C5—C4—C1121.2 (5)N2—C10—H10A120.0
C5—C4—H4A119.4C7—C10—H10A120.0
C1—C4—H4A119.4C10—C7—C6120.0
C20—C21—C24121.2 (5)C10—C7—H7A120.0
C20—C21—H21119.4C6—C7—H7A120.0
C24—C21—H21119.4C8'—C6'—C7'120.0
O3—C26—O4122.4 (6)C8'—C6'—C5116.8 (11)
O3—C26—C25123.5 (6)C7'—C6'—C5123.1 (11)
O4—C26—C25114.1 (5)C9'—C8'—C6'120.0
O1—C11—O2126.1 (6)C9'—C8'—H8'A120.0
O1—C11—C12117.4 (6)C6'—C8'—H8'A120.0
O2—C11—C12116.5 (5)C8'—C9'—N2'120.0
C25—C24—C21120.1 (5)C8'—C9'—H9'A120.0
C25—C24—H24119.9N2'—C9'—H9'A120.0
C21—C24—H24119.9C9'—N2'—C10'120.0
C12—C14—C15121.1 (5)C9'—N2'—Ag1124.6 (8)
C12—C14—H14119.5C10'—N2'—Ag1113.7 (9)
C15—C14—H14119.5C7'—C10'—N2'120.0
C25—C23—C22120.1 (5)C7'—C10'—H10B120.0
C25—C23—H23119.9N2'—C10'—H10B120.0
C22—C23—H23119.9C10'—C7'—C6'120.0
C13—C16—C17120.9 (5)C10'—C7'—H7'A120.0
C13—C16—H16119.6C6'—C7'—H7'A120.0
C1—N1—C2—C30.3 (9)C18—C17—C15—C14173.7 (5)
Ag1iii—N1—C2—C3177.2 (5)C12—C14—C15—C170.9 (9)
C16—C13—C12—C142.5 (8)C2—N1—C1—C40.3 (9)
C16—C13—C12—C11176.4 (5)Ag1iii—N1—C1—C4176.4 (5)
N1—C2—C3—C50.8 (10)C5—C4—C1—N10.4 (10)
C4—C5—C3—C20.7 (9)C19—O9—C18—C1774.5 (7)
C6'—C5—C3—C2177.3 (8)C15—C17—C18—O9131.7 (6)
C6—C5—C3—C2179.2 (6)C16—C17—C18—O953.1 (8)
C3—C5—C4—C10.2 (9)C4—C5—C6—C8159.2 (6)
C6'—C5—C4—C1177.9 (8)C3—C5—C6—C820.8 (8)
C6—C5—C4—C1179.8 (6)C6'—C5—C6—C8101 (34)
C22—C20—C21—C240.1 (9)C4—C5—C6—C722.8 (8)
C19—C20—C21—C24177.5 (5)C3—C5—C6—C7157.2 (6)
C24—C25—C26—O36.0 (9)C6'—C5—C6—C777 (34)
C23—C25—C26—O3173.9 (5)C7—C6—C8—C90.0
C24—C25—C26—O4173.9 (5)C5—C6—C8—C9177.9 (6)
C23—C25—C26—O46.1 (8)C6—C8—C9—N20.0
Ag1—O1—C11—O222.2 (7)C8—C9—N2—C100.0
Ag1—O1—C11—C12156.2 (3)C8—C9—N2—Ag1171.1 (4)
C14—C12—C11—O1167.6 (5)C9—N2—C10—C70.0
C13—C12—C11—O113.5 (8)Ag1—N2—C10—C7170.9 (4)
C14—C12—C11—O210.9 (7)N2—C10—C7—C60.0
C13—C12—C11—O2167.9 (5)C8—C6—C7—C100.0
C23—C25—C24—C210.6 (8)C5—C6—C7—C10178.0 (6)
C26—C25—C24—C21179.4 (5)C4—C5—C6'—C8'170.1 (8)
C20—C21—C24—C250.4 (9)C3—C5—C6'—C8'7.8 (13)
C13—C12—C14—C151.2 (8)C6—C5—C6'—C8'109 (35)
C11—C12—C14—C15177.7 (5)C4—C5—C6'—C7'12.9 (13)
C24—C25—C23—C220.4 (8)C3—C5—C6'—C7'169.2 (8)
C26—C25—C23—C22179.7 (5)C6—C5—C6'—C7'68 (34)
C12—C13—C16—C171.7 (9)C7'—C6'—C8'—C9'0.0
C13—C16—C17—C150.4 (9)C5—C6'—C8'—C9'177.1 (12)
C13—C16—C17—C18174.9 (5)C6'—C8'—C9'—N2'0.0
C21—C20—C22—C230.4 (8)C8'—C9'—N2'—C10'0.0
C19—C20—C22—C23177.8 (5)C8'—C9'—N2'—Ag1164.0 (11)
C25—C23—C22—C200.1 (8)C9'—N2'—C10'—C7'0.0
C18—O9—C19—C20170.2 (5)Ag1—N2'—C10'—C7'165.7 (9)
C22—C20—C19—O9171.3 (5)N2'—C10'—C7'—C6'0.0
C21—C20—C19—O96.1 (8)C8'—C6'—C7'—C10'0.0
C16—C17—C15—C141.7 (9)C5—C6'—C7'—C10'176.9 (13)
Symmetry codes: (i) x+1, y1, z; (ii) x+1, y+1, z+1; (iii) x1, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4···O2iv0.821.782.530 (5)152
Symmetry code: (iv) x+1, y+1, z.
 

Follow Acta Cryst. C
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds