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Acta Crystallogr Sect E Struct Rep Online. 2009 February 1; 65(Pt 2): m223.
Published online 2009 January 23. doi:  10.1107/S1600536809001184
PMCID: PMC2968213

Poly[bis­(μ-hemihydrogen 2-phenyl­quinoline-4-carboxyl­ato-κ2 N,O)silver(I)]

Abstract

In the title compound, [Ag(C16H10.5NO2)2], the AgI cation (site symmetry 2) is coordinated by two N atoms in a near-linear AgN2 arrangement. Two carboxyl­ate O atoms from two additional 2-phenyl­quinoline-4-carboxyl­ate ligands form long Ag—O bonds [2.6585 (17) Å], resulting in a distorted square-planar arrangement. The bridging ligands result in infinite corrugated sheets propagating in (010). An O—H(...)O hydrogen bond, disordered about a twofold axis, completes the structure.

Related literature

For the related coordination polymers containing MnII, CoII and CuII, see: Xiao et al. (2005 [triangle]); Xie et al. (2005 [triangle]) and Xie et al. (2006 [triangle]), respectively.

An external file that holds a picture, illustration, etc.
Object name is e-65-0m223-scheme1.jpg

Experimental

Crystal data

  • [Ag(C16H10.5NO2)2]
  • M r = 605.38
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m223-efi1.jpg
  • a = 7.2163 (6) Å
  • b = 20.5060 (17) Å
  • c = 16.5632 (12) Å
  • β = 97.585 (3)°
  • V = 2429.5 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.87 mm−1
  • T = 293 (2) K
  • 0.20 × 0.15 × 0.15 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2001 [triangle]) T min = 0.877, T max = 1.00 (expected range = 0.769–0.877)
  • 9257 measured reflections
  • 2791 independent reflections
  • 2550 reflections with I > 2σ(I)
  • R int = 0.020

Refinement

  • R[F 2 > 2σ(F 2)] = 0.029
  • wR(F 2) = 0.067
  • S = 1.10
  • 2791 reflections
  • 177 parameters
  • H-atom parameters constrained
  • Δρmax = 0.66 e Å−3
  • Δρmin = −0.33 e Å−3

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT (Bruker, 2001 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Selected geometric parameters (Å, °)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809001184/hb2825sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809001184/hb2825Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Experimental

A mixture of silver nitrate (0.5 mmol) and 2-phenyl-4-quinolinecarboxylic acid (0.5 mmol) in H2O (8 ml) and ethanol (8 ml) was sealed in a 25 ml Teflon-lined stainless steel autoclave and kept at 413 K for three days. Orange prisms of (I) were obtained after cooling to room temperature with a yield of 27%. Anal. Calc. for C32H21AgN2O4: C 63.43, H 3.47, N 4.63%; Found: C 63.41, H 3.32, N 4.59%.

Refinement

The H atoms were placed in calculated positions (C—H = 0.93 Å, O—H = 0.82Å) and refined as riding with and Uiso(H) = 1.2Ueq(carruer).

Figures

Fig. 1.
A view of the structure of (I), expanded to show the Ag—N bonds, showing 30% probability displacement ellipsoids. Symmetry code: I: 1–x, y, –z–1/2.
Fig. 2.
Part of a polymeric sheet in (I).

Crystal data

[Ag(C16H10.5NO2)2]F(000) = 1224
Mr = 605.38Dx = 1.655 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 3290 reflections
a = 7.2163 (6) Åθ = 2.3–27.5°
b = 20.5060 (17) ŵ = 0.87 mm1
c = 16.5632 (12) ÅT = 293 K
β = 97.585 (3)°Prism, orange
V = 2429.5 (3) Å30.20 × 0.15 × 0.15 mm
Z = 4

Data collection

Bruker SMART CCD diffractometer2791 independent reflections
Radiation source: fine-focus sealed tube2550 reflections with I > 2σ(I)
graphiteRint = 0.020
ω scansθmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)h = −9→9
Tmin = 0.877, Tmax = 1.00k = −25→26
9257 measured reflectionsl = −21→20

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.029Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.067H-atom parameters constrained
S = 1.10w = 1/[σ2(Fo2) + (0.0323P)2 + 1.551P] where P = (Fo2 + 2Fc2)/3
2791 reflections(Δ/σ)max < 0.001
177 parametersΔρmax = 0.66 e Å3
0 restraintsΔρmin = −0.33 e Å3

Special details

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)

xyzUiso*/UeqOcc. (<1)
Ag10.50000.224313 (10)−0.25000.03976 (9)
N10.4524 (2)0.22681 (7)−0.11903 (9)0.0305 (3)
O10.4807 (3)0.16931 (8)0.17478 (8)0.0506 (4)
H1O0.47500.17500.22340.061*0.50
O20.6459 (3)0.26118 (9)0.18437 (10)0.0555 (4)
C10.4841 (3)0.28414 (9)−0.07613 (11)0.0323 (4)
C20.4827 (4)0.34294 (10)−0.12074 (13)0.0468 (5)
H2A0.46190.3417−0.17730.056*
C30.5113 (4)0.40127 (11)−0.08202 (16)0.0562 (7)
H3A0.50940.4396−0.11210.067*
C40.5437 (4)0.40349 (11)0.00334 (16)0.0546 (6)
H4A0.56270.44360.02940.065*
C50.5477 (3)0.34808 (11)0.04857 (13)0.0446 (5)
H5A0.57120.35060.10510.054*
C60.5165 (3)0.28627 (9)0.01036 (11)0.0317 (4)
C70.5077 (3)0.22584 (9)0.05293 (11)0.0313 (4)
C80.4621 (3)0.17105 (10)0.00812 (11)0.0344 (4)
H8A0.44670.13190.03480.041*
C90.4376 (3)0.17227 (9)−0.07805 (10)0.0302 (4)
C100.3928 (3)0.11103 (9)−0.12467 (11)0.0331 (4)
C110.2740 (3)0.11181 (10)−0.19829 (12)0.0379 (4)
H11A0.22190.1510−0.21850.045*
C120.2330 (3)0.05444 (12)−0.24147 (13)0.0476 (5)
H12A0.15580.0555−0.29110.057*
C130.3063 (4)−0.00390 (12)−0.21119 (15)0.0570 (7)
H13A0.2773−0.0424−0.23990.068*
C140.4230 (4)−0.00520 (11)−0.13802 (15)0.0593 (7)
H14A0.4731−0.0446−0.11770.071*
C150.4659 (4)0.05159 (11)−0.09489 (12)0.0463 (5)
H15A0.54420.0502−0.04560.056*
C160.5497 (3)0.22006 (10)0.14510 (11)0.0356 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Ag10.05874 (17)0.04506 (14)0.01656 (11)0.0000.00894 (9)0.000
N10.0388 (9)0.0352 (8)0.0176 (7)0.0017 (7)0.0040 (6)0.0002 (6)
O10.0877 (12)0.0478 (8)0.0152 (6)−0.0092 (8)0.0029 (7)−0.0008 (6)
O20.0607 (11)0.0753 (11)0.0275 (8)−0.0222 (9)−0.0048 (7)−0.0068 (7)
C10.0384 (10)0.0364 (10)0.0232 (9)0.0005 (8)0.0081 (8)−0.0004 (7)
C20.0718 (16)0.0412 (11)0.0289 (10)0.0025 (11)0.0122 (10)0.0043 (8)
C30.085 (2)0.0358 (11)0.0494 (14)−0.0001 (11)0.0162 (13)0.0038 (10)
C40.0766 (18)0.0373 (11)0.0498 (14)−0.0021 (11)0.0084 (12)−0.0110 (10)
C50.0549 (14)0.0462 (12)0.0330 (11)0.0004 (10)0.0066 (10)−0.0110 (9)
C60.0331 (10)0.0391 (10)0.0236 (9)0.0001 (8)0.0060 (7)−0.0047 (7)
C70.0313 (10)0.0447 (10)0.0179 (8)0.0001 (8)0.0036 (7)−0.0016 (7)
C80.0485 (12)0.0369 (9)0.0179 (8)−0.0024 (9)0.0046 (8)0.0019 (7)
C90.0364 (10)0.0368 (9)0.0176 (8)0.0005 (8)0.0039 (7)0.0010 (7)
C100.0457 (12)0.0347 (9)0.0194 (8)−0.0039 (8)0.0066 (8)0.0005 (7)
C110.0447 (12)0.0434 (11)0.0252 (9)−0.0031 (9)0.0035 (8)0.0000 (8)
C120.0557 (14)0.0549 (13)0.0309 (10)−0.0146 (11)0.0007 (10)−0.0074 (9)
C130.088 (2)0.0440 (12)0.0401 (12)−0.0171 (12)0.0113 (12)−0.0106 (10)
C140.101 (2)0.0359 (11)0.0414 (13)0.0018 (12)0.0110 (13)0.0044 (9)
C150.0723 (16)0.0412 (11)0.0243 (10)0.0009 (10)0.0023 (10)0.0027 (8)
C160.0385 (11)0.0488 (11)0.0193 (8)0.0033 (9)0.0031 (8)−0.0040 (8)

Geometric parameters (Å, °)

Ag1—N12.2413 (15)C5—H5A0.9300
Ag1—N1i2.2413 (15)C6—C71.431 (3)
Ag1—O2ii2.6585 (17)C7—C81.363 (3)
Ag1—O2iii2.6585 (17)C7—C161.521 (2)
N1—C91.320 (2)C8—C91.415 (2)
N1—C11.377 (2)C8—H8A0.9300
O1—C161.280 (2)C9—C101.487 (3)
O1—H1O0.8200C10—C151.392 (3)
O2—C161.223 (3)C10—C111.395 (3)
O2—Ag1iii2.6585 (17)C11—C121.388 (3)
C1—C21.414 (3)C11—H11A0.9300
C1—C61.421 (3)C12—C131.376 (4)
C2—C31.360 (3)C12—H12A0.9300
C2—H2A0.9300C13—C141.382 (4)
C3—C41.403 (4)C13—H13A0.9300
C3—H3A0.9300C14—C151.380 (3)
C4—C51.359 (3)C14—H14A0.9300
C4—H4A0.9300C15—H15A0.9300
C5—C61.421 (3)
N1—Ag1—N1i177.38 (8)C8—C7—C16118.96 (17)
N1—Ag1—O2ii97.54 (6)C6—C7—C16123.08 (16)
N1i—Ag1—O2ii82.16 (6)C7—C8—C9121.59 (18)
N1—Ag1—O2iii82.16 (6)C7—C8—H8A119.2
N1i—Ag1—O2iii97.54 (6)C9—C8—H8A119.2
O2ii—Ag1—O2iii167.15 (8)N1—C9—C8121.72 (17)
C9—N1—C1118.51 (16)N1—C9—C10118.39 (15)
C9—N1—Ag1120.76 (12)C8—C9—C10119.90 (16)
C1—N1—Ag1118.86 (11)C15—C10—C11118.69 (18)
C16—O1—H1O109.5C15—C10—C9120.59 (18)
C16—O2—Ag1iii137.88 (16)C11—C10—C9120.70 (17)
N1—C1—C2117.98 (17)C12—C11—C10120.3 (2)
N1—C1—C6122.71 (17)C12—C11—H11A119.8
C2—C1—C6119.30 (17)C10—C11—H11A119.8
C3—C2—C1120.9 (2)C13—C12—C11120.3 (2)
C3—C2—H2A119.6C13—C12—H12A119.9
C1—C2—H2A119.6C11—C12—H12A119.9
C2—C3—C4119.9 (2)C12—C13—C14119.8 (2)
C2—C3—H3A120.0C12—C13—H13A120.1
C4—C3—H3A120.0C14—C13—H13A120.1
C5—C4—C3121.1 (2)C15—C14—C13120.5 (2)
C5—C4—H4A119.4C15—C14—H14A119.8
C3—C4—H4A119.4C13—C14—H14A119.8
C4—C5—C6120.6 (2)C14—C15—C10120.5 (2)
C4—C5—H5A119.7C14—C15—H15A119.8
C6—C5—H5A119.7C10—C15—H15A119.8
C5—C6—C1118.14 (18)O2—C16—O1125.35 (19)
C5—C6—C7124.57 (18)O2—C16—C7120.26 (18)
C1—C6—C7117.24 (16)O1—C16—C7114.37 (17)
C8—C7—C6117.95 (17)

Symmetry codes: (i) −x+1, y, −z−1/2; (ii) x−1/2, −y+1/2, z−1/2; (iii) −x+3/2, −y+1/2, −z.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1O···O1iv0.821.682.470 (3)162

Symmetry codes: (iv) −x+1, y, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2825).

References

  • Bruker (2001). SMART, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Xiao, H. P., Li, X.-H. & Cheng, Y.-Q. (2005). Acta Cryst. E61, m158–m159.
  • Xie, G., Zeng, M.-H., Chen, S.-P. & Gao, S.-L. (2005). Acta Cryst. E61, m2273–m2275.
  • Xie, G., Zeng, M.-H., Chen, S.-P. & Gao, S.-L. (2006). Acta Cryst. E62, m397–m399.

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