Poly[bis­(μ-hemihydrogen 2-phenyl­quinoline-4-carboxyl­ato-κ2N,O)silver(I)]

Zhang, X.; Wei, P.; Li, B.

doi:10.1107/S1600536809001184

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page m223

doi:10.1107/S1600536809001184

Open

access

ADDENDA AND ERRATA

A correction has been published for this article. To view the correction, click here.

Poly[bis(μ-hemihydrogen 2-phenylquinoline-4-carboxylato-κ²N,O)silver(I)]

Xiutang Zhang,^a,^b ^* Peihai Wei ^b and Bin Li ^c

^aAdvanced Material Institute of Research, Department of Chemistry and Chemical Engineering, Shandong Institute of Education, Jinan, 250013, People's Republic of China, ^bCollege of Chemistry and Chemical Engineering, Liaocheng University, Liaocheng, 252059, People's Republic of China, and ^cDepartment of Chemistry and Chemical Engineering, Shandong Institute of Education, Jinan 250013, People's Republic of China
^*Correspondence e-mail: xiutangzhang@yahoo.com.cn

(Received 21 October 2008; accepted 10 January 2009; online 23 January 2009)

In the title compound, [Ag(C₁₆H_10.5NO₂)₂], the Ag^I 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 Mn^II, Co^II and Cu^II, see: Xiao et al. (2005 ); Xie et al. (2005 ) and Xie et al. (2006 ), respectively.

Experimental

Crystal data

[Ag(C₁₆H_10.5NO₂)₂]
M_r = 605.38
Monoclinic, C 2/c
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 ) 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[F² > 2σ(F²)] = 0.029
wR(F²) = 0.067
S = 1.10
2791 reflections
177 parameters
H-atom parameters constrained
Δρ_max = 0.66 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Ag1—N1	2.2413 (15)

N1—Ag1—N1ⁱ	177.38 (8)
Symmetry code: (i) $[-x+1, y, -z-{\script{1\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯O1ⁱⁱ	0.82	1.68	2.470 (3)	162
Symmetry code: (ii) $[-x+1, y, -z+{\script{1\over 2}}]$ .

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

Supporting information

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

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

checkCIF report

Related literature top

For the related coordination polymers containing Mn^II, Co^II and Cu^II, see: Xiao et al. (2005); Xie et al. (2005) and Xie et al. (2006), respectively.

Experimental top

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%.

Computing details top

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

Figures top

	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).

Poly[bis(µ-hemihydrogen 2-phenylquinoline-4-carboxylato-κ²N,O)silver(I)] top

Crystal data top

[Ag(C₁₆H_10.5NO₂)₂]	F(000) = 1224
M_r = 605.38	D_x = 1.655 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3290 reflections
a = 7.2163 (6) Å	θ = 2.3–27.5°
b = 20.5060 (17) Å	µ = 0.87 mm⁻¹
c = 16.5632 (12) Å	T = 293 K
β = 97.585 (3)°	Prism, orange
V = 2429.5 (3) Å³	0.20 × 0.15 × 0.15 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	2791 independent reflections
Radiation source: fine-focus sealed tube	2550 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ω scans	θ_max = 27.5°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→9
T_min = 0.877, T_max = 1.00	k = −25→26
9257 measured reflections	l = −21→20

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.067	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0323P)² + 1.551P] where P = (F_o² + 2F_c²)/3
2791 reflections	(Δ/σ)_max < 0.001
177 parameters	Δρ_max = 0.66 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

[Ag(C₁₆H_10.5NO₂)₂]	V = 2429.5 (3) Å³
M_r = 605.38	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 7.2163 (6) Å	µ = 0.87 mm⁻¹
b = 20.5060 (17) Å	T = 293 K
c = 16.5632 (12) Å	0.20 × 0.15 × 0.15 mm
β = 97.585 (3)°

Data collection top

Bruker SMART CCD diffractometer	2791 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2550 reflections with I > 2σ(I)
T_min = 0.877, T_max = 1.00	R_int = 0.020
9257 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.067	H-atom parameters constrained
S = 1.10	Δρ_max = 0.66 e Å⁻³
2791 reflections	Δρ_min = −0.33 e Å⁻³
177 parameters

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	U_iso*/U_eq	Occ. (<1)
Ag1	0.5000	0.224313 (10)	−0.2500	0.03976 (9)
N1	0.4524 (2)	0.22681 (7)	−0.11903 (9)	0.0305 (3)
O1	0.4807 (3)	0.16931 (8)	0.17478 (8)	0.0506 (4)
H1O	0.4750	0.1750	0.2234	0.061*	0.50
O2	0.6459 (3)	0.26118 (9)	0.18437 (10)	0.0555 (4)
C1	0.4841 (3)	0.28414 (9)	−0.07613 (11)	0.0323 (4)
C2	0.4827 (4)	0.34294 (10)	−0.12074 (13)	0.0468 (5)
H2A	0.4619	0.3417	−0.1773	0.056*
C3	0.5113 (4)	0.40127 (11)	−0.08202 (16)	0.0562 (7)
H3A	0.5094	0.4396	−0.1121	0.067*
C4	0.5437 (4)	0.40349 (11)	0.00334 (16)	0.0546 (6)
H4A	0.5627	0.4436	0.0294	0.065*
C5	0.5477 (3)	0.34808 (11)	0.04857 (13)	0.0446 (5)
H5A	0.5712	0.3506	0.1051	0.054*
C6	0.5165 (3)	0.28627 (9)	0.01036 (11)	0.0317 (4)
C7	0.5077 (3)	0.22584 (9)	0.05293 (11)	0.0313 (4)
C8	0.4621 (3)	0.17105 (10)	0.00812 (11)	0.0344 (4)
H8A	0.4467	0.1319	0.0348	0.041*
C9	0.4376 (3)	0.17227 (9)	−0.07805 (10)	0.0302 (4)
C10	0.3928 (3)	0.11103 (9)	−0.12467 (11)	0.0331 (4)
C11	0.2740 (3)	0.11181 (10)	−0.19829 (12)	0.0379 (4)
H11A	0.2219	0.1510	−0.2185	0.045*
C12	0.2330 (3)	0.05444 (12)	−0.24147 (13)	0.0476 (5)
H12A	0.1558	0.0555	−0.2911	0.057*
C13	0.3063 (4)	−0.00390 (12)	−0.21119 (15)	0.0570 (7)
H13A	0.2773	−0.0424	−0.2399	0.068*
C14	0.4230 (4)	−0.00520 (11)	−0.13802 (15)	0.0593 (7)
H14A	0.4731	−0.0446	−0.1177	0.071*
C15	0.4659 (4)	0.05159 (11)	−0.09489 (12)	0.0463 (5)
H15A	0.5442	0.0502	−0.0456	0.056*
C16	0.5497 (3)	0.22006 (10)	0.14510 (11)	0.0356 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.05874 (17)	0.04506 (14)	0.01656 (11)	0.000	0.00894 (9)	0.000
N1	0.0388 (9)	0.0352 (8)	0.0176 (7)	0.0017 (7)	0.0040 (6)	0.0002 (6)
O1	0.0877 (12)	0.0478 (8)	0.0152 (6)	−0.0092 (8)	0.0029 (7)	−0.0008 (6)
O2	0.0607 (11)	0.0753 (11)	0.0275 (8)	−0.0222 (9)	−0.0048 (7)	−0.0068 (7)
C1	0.0384 (10)	0.0364 (10)	0.0232 (9)	0.0005 (8)	0.0081 (8)	−0.0004 (7)
C2	0.0718 (16)	0.0412 (11)	0.0289 (10)	0.0025 (11)	0.0122 (10)	0.0043 (8)
C3	0.085 (2)	0.0358 (11)	0.0494 (14)	−0.0001 (11)	0.0162 (13)	0.0038 (10)
C4	0.0766 (18)	0.0373 (11)	0.0498 (14)	−0.0021 (11)	0.0084 (12)	−0.0110 (10)
C5	0.0549 (14)	0.0462 (12)	0.0330 (11)	0.0004 (10)	0.0066 (10)	−0.0110 (9)
C6	0.0331 (10)	0.0391 (10)	0.0236 (9)	0.0001 (8)	0.0060 (7)	−0.0047 (7)
C7	0.0313 (10)	0.0447 (10)	0.0179 (8)	0.0001 (8)	0.0036 (7)	−0.0016 (7)
C8	0.0485 (12)	0.0369 (9)	0.0179 (8)	−0.0024 (9)	0.0046 (8)	0.0019 (7)
C9	0.0364 (10)	0.0368 (9)	0.0176 (8)	0.0005 (8)	0.0039 (7)	0.0010 (7)
C10	0.0457 (12)	0.0347 (9)	0.0194 (8)	−0.0039 (8)	0.0066 (8)	0.0005 (7)
C11	0.0447 (12)	0.0434 (11)	0.0252 (9)	−0.0031 (9)	0.0035 (8)	0.0000 (8)
C12	0.0557 (14)	0.0549 (13)	0.0309 (10)	−0.0146 (11)	0.0007 (10)	−0.0074 (9)
C13	0.088 (2)	0.0440 (12)	0.0401 (12)	−0.0171 (12)	0.0113 (12)	−0.0106 (10)
C14	0.101 (2)	0.0359 (11)	0.0414 (13)	0.0018 (12)	0.0110 (13)	0.0044 (9)
C15	0.0723 (16)	0.0412 (11)	0.0243 (10)	0.0009 (10)	0.0023 (10)	0.0027 (8)
C16	0.0385 (11)	0.0488 (11)	0.0193 (8)	0.0033 (9)	0.0031 (8)	−0.0040 (8)

Geometric parameters (Å, º) top

Ag1—N1	2.2413 (15)	C5—H5A	0.9300
Ag1—N1ⁱ	2.2413 (15)	C6—C7	1.431 (3)
Ag1—O2ⁱⁱ	2.6585 (17)	C7—C8	1.363 (3)
Ag1—O2ⁱⁱⁱ	2.6585 (17)	C7—C16	1.521 (2)
N1—C9	1.320 (2)	C8—C9	1.415 (2)
N1—C1	1.377 (2)	C8—H8A	0.9300
O1—C16	1.280 (2)	C9—C10	1.487 (3)
O1—H1O	0.8200	C10—C15	1.392 (3)
O2—C16	1.223 (3)	C10—C11	1.395 (3)
O2—Ag1ⁱⁱⁱ	2.6585 (17)	C11—C12	1.388 (3)
C1—C2	1.414 (3)	C11—H11A	0.9300
C1—C6	1.421 (3)	C12—C13	1.376 (4)
C2—C3	1.360 (3)	C12—H12A	0.9300
C2—H2A	0.9300	C13—C14	1.382 (4)
C3—C4	1.403 (4)	C13—H13A	0.9300
C3—H3A	0.9300	C14—C15	1.380 (3)
C4—C5	1.359 (3)	C14—H14A	0.9300
C4—H4A	0.9300	C15—H15A	0.9300
C5—C6	1.421 (3)

N1—Ag1—N1ⁱ	177.38 (8)	C8—C7—C16	118.96 (17)
N1—Ag1—O2ⁱⁱ	97.54 (6)	C6—C7—C16	123.08 (16)
N1ⁱ—Ag1—O2ⁱⁱ	82.16 (6)	C7—C8—C9	121.59 (18)
N1—Ag1—O2ⁱⁱⁱ	82.16 (6)	C7—C8—H8A	119.2
N1ⁱ—Ag1—O2ⁱⁱⁱ	97.54 (6)	C9—C8—H8A	119.2
O2ⁱⁱ—Ag1—O2ⁱⁱⁱ	167.15 (8)	N1—C9—C8	121.72 (17)
C9—N1—C1	118.51 (16)	N1—C9—C10	118.39 (15)
C9—N1—Ag1	120.76 (12)	C8—C9—C10	119.90 (16)
C1—N1—Ag1	118.86 (11)	C15—C10—C11	118.69 (18)
C16—O1—H1O	109.5	C15—C10—C9	120.59 (18)
C16—O2—Ag1ⁱⁱⁱ	137.88 (16)	C11—C10—C9	120.70 (17)
N1—C1—C2	117.98 (17)	C12—C11—C10	120.3 (2)
N1—C1—C6	122.71 (17)	C12—C11—H11A	119.8
C2—C1—C6	119.30 (17)	C10—C11—H11A	119.8
C3—C2—C1	120.9 (2)	C13—C12—C11	120.3 (2)
C3—C2—H2A	119.6	C13—C12—H12A	119.9
C1—C2—H2A	119.6	C11—C12—H12A	119.9
C2—C3—C4	119.9 (2)	C12—C13—C14	119.8 (2)
C2—C3—H3A	120.0	C12—C13—H13A	120.1
C4—C3—H3A	120.0	C14—C13—H13A	120.1
C5—C4—C3	121.1 (2)	C15—C14—C13	120.5 (2)
C5—C4—H4A	119.4	C15—C14—H14A	119.8
C3—C4—H4A	119.4	C13—C14—H14A	119.8
C4—C5—C6	120.6 (2)	C14—C15—C10	120.5 (2)
C4—C5—H5A	119.7	C14—C15—H15A	119.8
C6—C5—H5A	119.7	C10—C15—H15A	119.8
C5—C6—C1	118.14 (18)	O2—C16—O1	125.35 (19)
C5—C6—C7	124.57 (18)	O2—C16—C7	120.26 (18)
C1—C6—C7	117.24 (16)	O1—C16—C7	114.37 (17)
C8—C7—C6	117.95 (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, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O1^iv	0.82	1.68	2.470 (3)	162

Symmetry code: (iv) −x+1, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Ag(C₁₆H_10.5NO₂)₂]
M_r	605.38
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	7.2163 (6), 20.5060 (17), 16.5632 (12)
β (°)	97.585 (3)
V (Å³)	2429.5 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.87
Crystal size (mm)	0.20 × 0.15 × 0.15

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.877, 1.00
No. of measured, independent and observed [I > 2σ(I)] reflections	9257, 2791, 2550
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.067, 1.10
No. of reflections	2791
No. of parameters	177
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.66, −0.33

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Ag1—N1	2.2413 (15)

N1—Ag1—N1ⁱ	177.38 (8)

Symmetry code: (i) −x+1, y, −z−1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O1ⁱⁱ	0.82	1.68	2.470 (3)	162

Symmetry code: (ii) −x+1, y, −z+1/2.

References

Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xiao, H. P., Li, X.-H. & Cheng, Y.-Q. (2005). Acta Cryst. E61, m158–m159. Web of Science CSD CrossRef IUCr Journals Google Scholar
Xie, G., Zeng, M.-H., Chen, S.-P. & Gao, S.-L. (2005). Acta Cryst. E61, m2273–m2275. Web of Science CSD CrossRef IUCr Journals Google Scholar
Xie, G., Zeng, M.-H., Chen, S.-P. & Gao, S.-L. (2006). Acta Cryst. E62, m397–m399. Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page m223

doi:10.1107/S1600536809001184

Open

access