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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 11| November 2010| Page m1482
https://doi.org/10.1107/S1600536810043199

catena-Poly[silver(I)-μ-acridine-9-carboxyl­ato-κ3N:O,O′]

Ya-Qing Yang,a Xiao-Ye Chen,a Shu-Min Huo,a Yan-Ru Maa and Rong-Hua Zenga,b*

aSchool of Chemistry and Environment, South China Normal University, Guangzhou 510006, People's Republic of China, and bKey Laboratory of Technology on Electrochemical Energy Storage and Power Generation in Guangdong Universities, South China Normal University, Guangzhou 510006, People's Republic of China
*Correspondence e-mail: zrh321@yahoo.com.cn

(Received 15 October 2010; accepted 23 October 2010; online 30 October 2010)

In the title coordination polymer, [Ag(C14H8NO2)]n, the AgI cation is coordinated by two O atoms and one N atom from two symmetry-related acridine-9-carboxyl­ate ligands in a distorted trigonal-planar geometry. The metal atoms are connected by the ligands to form chains running parallel to the b axis. π–π stacking inter­actions [centroid-to-centroid distances 3.757 (2)–3.820 (2) Å] and weak Ag⋯O inter­actions further link the chains to form a layer network parallel to the ab plane. The AgI cation is disordered over two positions, with refined site-occupancy factors of 0.73 (3):0.27 (3).

Related literature

For the structures of related metal complexes of acridine-9-carboxyl­ate, see: Bu, Tong, Chang et al. (2005[Bu, X.-H., Tong, M.-L., Chang, H.-C., Kitagawa, S. & Batten, S.-R. (2005). Angew. Chem. Int. Ed. 43, 192-195.]); Bu, Tong, Li et al. (2005[Bu, X.-H., Tong, M.-L., Li, J.-R., Chang, H.-C., Li, L.-J. & Kitagawa, S. (2005). CrystEngComm, 7, 411-416.]); Bu, Tong, Xie et al. (2005[Bu, X.-H., Tong, M.-L., Xie, Y.-B., Li, J.-R., Chang, H.-C., Kitagawa, S. & Ribas, J. (2005). Inorg. Chem. 44, 9837-9846.]).

[Scheme 1]

Experimental

Crystal data

  • [Ag(C14H8NO2)]

  • Mr = 330.08

  • Monoclinic, P 21 /c

  • a = 7.5622 (7) Å

  • b = 9.2210 (9) Å

  • c = 16.4451 (14) Å

  • β = 111.494 (4)°

  • V = 1066.99 (17) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 1.88 mm−1

  • T = 273 K

  • 0.22 × 0.19 × 0.17 mm
Data collection

  • Bruker APEXII area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) Tmin = 0.683, Tmax = 0.741

  • 5598 measured reflections

  • 2084 independent reflections

  • 1567 reflections with I > 2σ(I)

  • Rint = 0.023
Refinement

  • R[F2 > 2σ(F2)] = 0.029

  • wR(F2) = 0.077

  • S = 1.06

  • 2084 reflections

  • 173 parameters

  • H-atom parameters constrained

  • Δρmax = 0.54 e Å−3

  • Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810043199/rz2505sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810043199/rz2505Isup2.hkl

checkCIF report


Comment top

In the synthesis of novel metal organic frameworks (MOFs), ligands play a key role in the construction of coordination polymers with fascinating topologies, intriguing architectures and useful physical-chemical properties. The acridine-9-carboxylate anion is a potential bifunctional ligand with carboxylate and N-donor functional groups which has been used to prepare metal organic complexes possessing multidimensional networks and interesting properties (Bu, Tong, Chang et al., 2005; Bu, Tong, Li et al., 2005; Bu, Tong, Xie et al., 2005). Herein, we report the crystal structure of a novel polymeric silver(I) complex synthesized by the hydrothermal reaction of AgNO3 with acridine-9-carboxylic acid in aqueous solution.

As shown in Fig. 1, the asymmetric unit of the title compound consists of a disordered silver(I) ion and one acridine-9-carboxylate anion. The cation is three-coordinated in a distorted trigonal planar geometry by two O atoms and one N atom from two symmetry-related acridine-9-carboxylate ligands. The Ag···O and Ag···N bond lengths range from 2.158 (4) to 2.499 (4) Å and bond angles vary from 55.02 (2) to 154.1 (2)°. The acridine-9-carboxylate ligands connect the metal centres to generate chains parallel to the b axis. The chains are further connected by π–π stacking interactions (the centroid-to-centroid distances between neighbouring phenyl rings are 3.757 (2) and 3.820 (2) Å) and Ag···O weak interactions (2.844 (15)–3.348 (16) Å) to assemble a two-dimensional layer network parallel to the ab plane (Fig. 2).

Related literature top

For the structure of related metal complexes of acridine-9-carboxylate, see: Bu, Tong, Chang et al. (2005); Bu, Tong, Li et al. (2005); Bu, Tong, Xie et al. (2005).

Experimental top

A mixture of AgNO3 (0.170 g, 1 mmol), acridine-9-carboxylic acid (0.223 g, 1 mmol) and water (10 ml) was stirred vigorously for 60 min and then sealed in a Teflon-lined stainless-steel autoclave (20 ml capacity). The autoclave was heated and maintained at 423 K for 3 d, and then cooled to room temperature at 5 K h-1 and obtained the colourless block crystals.

Refinement top

The disordered silver ion was refined over two sites, with refined occupancies of 0.73 (3) and 0.27 (3). H atoms attached to C atoms were placed at calculated positions and were treated as riding on their parent atoms with C—H = 0.93 Å, and with Uiso(H) = 1.2Ueq(C).

Structure description top

In the synthesis of novel metal organic frameworks (MOFs), ligands play a key role in the construction of coordination polymers with fascinating topologies, intriguing architectures and useful physical-chemical properties. The acridine-9-carboxylate anion is a potential bifunctional ligand with carboxylate and N-donor functional groups which has been used to prepare metal organic complexes possessing multidimensional networks and interesting properties (Bu, Tong, Chang et al., 2005; Bu, Tong, Li et al., 2005; Bu, Tong, Xie et al., 2005). Herein, we report the crystal structure of a novel polymeric silver(I) complex synthesized by the hydrothermal reaction of AgNO3 with acridine-9-carboxylic acid in aqueous solution.

As shown in Fig. 1, the asymmetric unit of the title compound consists of a disordered silver(I) ion and one acridine-9-carboxylate anion. The cation is three-coordinated in a distorted trigonal planar geometry by two O atoms and one N atom from two symmetry-related acridine-9-carboxylate ligands. The Ag···O and Ag···N bond lengths range from 2.158 (4) to 2.499 (4) Å and bond angles vary from 55.02 (2) to 154.1 (2)°. The acridine-9-carboxylate ligands connect the metal centres to generate chains parallel to the b axis. The chains are further connected by π–π stacking interactions (the centroid-to-centroid distances between neighbouring phenyl rings are 3.757 (2) and 3.820 (2) Å) and Ag···O weak interactions (2.844 (15)–3.348 (16) Å) to assemble a two-dimensional layer network parallel to the ab plane (Fig. 2).

For the structure of related metal complexes of acridine-9-carboxylate, see: Bu, Tong, Chang et al. (2005); Bu, Tong, Li et al. (2005); Bu, Tong, Xie et al. (2005).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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
[Figure 1] Fig. 1. The molecular structure showing the atomic-numbering scheme. Displacement ellipsoids drawn at the 30% probability level. Symmetry codes: (#1) x, -1 + y, z; (#2) x, 1 + y, z.
[Figure 2] Fig. 2. A view of the two-dimensional layer network. π–π stacking and Ag···O interactions are shown as dashed lines.
catena-Poly[silver(I)-µ-acridine-9-carboxylato- κ3N:O,O'] top
Crystal data top
[Ag(C14H8NO2)]F(000) = 648
Mr = 330.08Dx = 2.055 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1873 reflections
a = 7.5622 (7) Åθ = 2.6–27.3°
b = 9.2210 (9) ŵ = 1.88 mm−1
c = 16.4451 (14) ÅT = 273 K
β = 111.494 (4)°Block, colourless
V = 1066.99 (17) Å30.22 × 0.19 × 0.17 mm
Z = 4
Data collection top
Bruker APEXII area-detector
diffractometer		2084 independent reflections
Radiation source: fine-focus sealed tube1567 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
φ and ω scanθmax = 26.0°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2008)		h = −9→9
Tmin = 0.683, Tmax = 0.741k = −8→11
5598 measured reflectionsl = −20→15
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)] = 0.029Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.077H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0359P)2 + 0.2862P]
where P = (Fo2 + 2Fc2)/3
2084 reflections(Δ/σ)max = 0.006
173 parametersΔρmax = 0.54 e Å−3
0 restraintsΔρmin = −0.30 e Å−3
Crystal data top
[Ag(C14H8NO2)]V = 1066.99 (17) Å3
Mr = 330.08Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.5622 (7) ŵ = 1.88 mm−1
b = 9.2210 (9) ÅT = 273 K
c = 16.4451 (14) Å0.22 × 0.19 × 0.17 mm
β = 111.494 (4)°
Data collection top
Bruker APEXII area-detector
diffractometer		2084 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2008)		1567 reflections with I > 2σ(I)
Tmin = 0.683, Tmax = 0.741Rint = 0.023
5598 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0290 restraints
wR(F2) = 0.077H-atom parameters constrained
S = 1.06Δρmax = 0.54 e Å−3
2084 reflectionsΔρmin = −0.30 e Å−3
173 parameters
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. 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 > 2sigma(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*/UeqOcc. (<1)
Ag10.2324 (8)0.3717 (4)0.01361 (19)0.0468 (5)0.73 (3)
O20.1974 (4)0.6015 (2)0.04076 (18)0.0513 (6)
O10.3266 (4)0.6125 (2)−0.06037 (17)0.0541 (7)
N10.2472 (3)1.1389 (2)0.00461 (13)0.0269 (5)
C5−0.1045 (4)0.9302 (3)−0.22018 (19)0.0364 (7)
H5−0.18130.8855−0.27170.044*
C40.0109 (4)0.8485 (3)−0.15332 (19)0.0327 (7)
H40.00940.7481−0.15910.039*
C6−0.1090 (4)1.0819 (3)−0.2124 (2)0.0357 (7)
H6−0.19081.1366−0.25830.043*
C70.0054 (4)1.1492 (3)−0.13802 (19)0.0330 (7)
H70.00041.2495−0.13360.040*
C80.1322 (4)1.0684 (3)−0.06708 (17)0.0250 (6)
C30.1345 (4)0.9134 (3)−0.07441 (18)0.0251 (6)
C20.2579 (4)0.8336 (3)−0.00469 (17)0.0269 (6)
C10.2628 (4)0.6678 (3)−0.00950 (19)0.0324 (7)
C140.3754 (4)0.9067 (3)0.07046 (18)0.0255 (6)
C130.5050 (4)0.8332 (3)0.14539 (19)0.0338 (7)
H130.51400.73260.14510.041*
C120.6146 (4)0.9089 (3)0.21674 (19)0.0362 (7)
H120.69750.85960.26500.043*
C110.6044 (4)1.0612 (3)0.21852 (19)0.0361 (7)
H110.67981.11160.26810.043*
C100.4860 (4)1.1349 (3)0.14873 (19)0.0332 (7)
H100.48281.23560.15070.040*
C90.3668 (4)1.0616 (3)0.07275 (17)0.0255 (6)
Ag1'0.270 (2)0.3775 (9)0.0018 (12)0.058 (2)0.27 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ag10.0732 (12)0.0133 (4)0.0485 (6)−0.0002 (5)0.0160 (5)−0.0003 (3)
O20.0680 (17)0.0186 (12)0.0686 (16)−0.0030 (11)0.0265 (14)0.0051 (11)
O10.0806 (18)0.0260 (12)0.0586 (15)0.0118 (12)0.0288 (14)−0.0036 (11)
N10.0321 (13)0.0161 (12)0.0316 (13)0.0028 (11)0.0108 (11)−0.0014 (10)
C50.0356 (18)0.0374 (18)0.0295 (15)−0.0038 (14)0.0040 (13)−0.0056 (13)
C40.0328 (16)0.0243 (16)0.0353 (15)−0.0014 (13)0.0055 (13)−0.0056 (12)
C60.0312 (17)0.0395 (18)0.0321 (16)0.0054 (14)0.0065 (13)0.0085 (13)
C70.0373 (17)0.0207 (15)0.0388 (16)0.0062 (13)0.0114 (13)0.0074 (12)
C80.0275 (15)0.0196 (13)0.0272 (14)0.0015 (12)0.0091 (12)0.0007 (11)
C30.0273 (15)0.0182 (13)0.0286 (14)−0.0022 (11)0.0088 (12)−0.0011 (11)
C20.0296 (15)0.0170 (14)0.0336 (16)−0.0001 (11)0.0108 (13)0.0015 (11)
C10.0323 (16)0.0229 (16)0.0328 (16)0.0025 (13)0.0011 (13)0.0004 (12)
C140.0266 (15)0.0199 (14)0.0285 (14)−0.0023 (11)0.0084 (12)0.0004 (11)
C130.0359 (17)0.0240 (15)0.0360 (16)0.0012 (13)0.0068 (13)0.0052 (12)
C120.0329 (17)0.0377 (18)0.0309 (15)0.0023 (14)0.0034 (13)0.0060 (13)
C110.0337 (17)0.0379 (18)0.0313 (16)−0.0059 (14)0.0054 (13)−0.0053 (14)
C100.0375 (17)0.0240 (15)0.0359 (15)−0.0061 (14)0.0110 (13)−0.0064 (13)
C90.0288 (15)0.0183 (13)0.0293 (14)−0.0025 (12)0.0105 (12)−0.0011 (12)
Ag1'0.074 (3)0.0130 (7)0.072 (4)−0.0051 (13)0.009 (2)0.0048 (15)
Geometric parameters (Å, º) top
Ag1—N1i2.158 (4)C7—C81.420 (4)
Ag1—O22.201 (4)C7—H70.9300
O2—C11.266 (4)C8—C31.435 (4)
O2—Ag1'2.290 (15)C3—C21.394 (4)
O1—C11.220 (4)C2—C141.402 (4)
O1—Ag1'2.499 (14)C2—C11.532 (4)
N1—C81.348 (3)C14—C91.432 (4)
N1—C91.356 (3)C14—C131.433 (4)
N1—Ag1ii2.158 (4)C13—C121.356 (4)
N1—Ag1'ii2.208 (8)C13—H130.9300
C5—C41.355 (4)C12—C111.408 (4)
C5—C61.406 (4)C12—H120.9300
C5—H50.9300C11—C101.352 (4)
C4—C31.424 (4)C11—H110.9300
C4—H40.9300C10—C91.416 (4)
C6—C71.362 (4)C10—H100.9300
C6—H60.9300Ag1'—N1i2.208 (8)
N1i—Ag1—O2170.0 (3)C3—C2—C14119.3 (3)
C1—O2—Ag1103.2 (2)C3—C2—C1120.4 (2)
C1—O2—Ag1'93.5 (6)C14—C2—C1120.4 (2)
C1—O1—Ag1'85.0 (6)O1—C1—O2126.4 (3)
C8—N1—C9119.4 (2)O1—C1—C2118.4 (3)
C8—N1—Ag1ii120.5 (2)O2—C1—C2115.2 (3)
C9—N1—Ag1ii120.12 (19)C2—C14—C9118.9 (2)
C8—N1—Ag1'ii119.5 (4)C2—C14—C13122.9 (3)
C9—N1—Ag1'ii120.5 (3)C9—C14—C13118.2 (3)
C4—C5—C6120.6 (3)C12—C13—C14120.6 (3)
C4—C5—H5119.7C12—C13—H13119.7
C6—C5—H5119.7C14—C13—H13119.7
C5—C4—C3121.2 (3)C13—C12—C11120.7 (3)
C5—C4—H4119.4C13—C12—H12119.6
C3—C4—H4119.4C11—C12—H12119.6
C7—C6—C5120.4 (3)C10—C11—C12120.5 (3)
C7—C6—H6119.8C10—C11—H11119.7
C5—C6—H6119.8C12—C11—H11119.7
C6—C7—C8120.9 (3)C11—C10—C9121.3 (3)
C6—C7—H7119.5C11—C10—H10119.4
C8—C7—H7119.5C9—C10—H10119.4
N1—C8—C7119.4 (2)N1—C9—C10119.7 (2)
N1—C8—C3122.0 (2)N1—C9—C14121.7 (2)
C7—C8—C3118.6 (3)C10—C9—C14118.6 (3)
C2—C3—C4123.1 (3)N1i—Ag1'—O2149.7 (13)
C2—C3—C8118.8 (2)N1i—Ag1'—O1154.1 (12)
C4—C3—C8118.1 (3)O2—Ag1'—O155.0 (2)
Symmetry codes: (i) x, y−1, z; (ii) x, y+1, z.

Experimental details

Crystal data
Chemical formula[Ag(C14H8NO2)]
Mr330.08
Crystal system, space groupMonoclinic, P21/c
Temperature (K)273
a, b, c (Å)7.5622 (7), 9.2210 (9), 16.4451 (14)
β (°) 111.494 (4)
V (Å3)1066.99 (17)
Z4
Radiation typeMo Kα
µ (mm−1)1.88
Crystal size (mm)0.22 × 0.19 × 0.17
Data collection
DiffractometerBruker APEXII area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2008)
Tmin, Tmax0.683, 0.741
No. of measured, independent and
observed [I > 2σ(I)] reflections		5598, 2084, 1567
Rint0.023
(sin θ/λ)max (Å−1)0.616
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.029, 0.077, 1.06
No. of reflections2084
No. of parameters173
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.54, −0.30

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

The authors acknowledge South China Normal University and the Key Laboratory of Technology on Electrochemical Energy Storage and Power Generation in Guangdong Universities for supporting this work.

References

First citationBruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationBu, X.-H., Tong, M.-L., Chang, H.-C., Kitagawa, S. & Batten, S.-R. (2005). Angew. Chem. Int. Ed. 43, 192–195.  Web of Science CSD CrossRef Google Scholar
 First citationBu, X.-H., Tong, M.-L., Li, J.-R., Chang, H.-C., Li, L.-J. & Kitagawa, S. (2005). CrystEngComm, 7, 411–416.  Web of Science CSD CrossRef CAS Google Scholar
 First citationBu, X.-H., Tong, M.-L., Xie, Y.-B., Li, J.-R., Chang, H.-C., Kitagawa, S. & Ribas, J. (2005). Inorg. Chem. 44, 9837–9846.  Web of Science CSD CrossRef PubMed CAS Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 11| November 2010| Page m1482
https://doi.org/10.1107/S1600536810043199
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