metal-organic compounds
Bis(pyridine-3-carboxylic acid-κN)silver(I) perchlorate
aDepartment of Chemistry, Bijie University, Bijie 551700, People's Republic of China
*Correspondence e-mail: liqz75@yahoo.com.cn
In the title compound, [Ag(C6H5NO2)2]ClO4, the AgI atom shows an almost linear coordination geometry, defined by two N atoms from two pyridine-3-carboxylic acid ligands. The complex cations are linked by hydrogen bonds between the carboxyl groups into a chain. The chains are further connected through C—H⋯O hydrogen bonds and a weak Ag⋯O interaction [2.757 (8) Å] into a layer. Another Ag⋯O interaction [2.899 (2) Å] and a C—H⋯O hydrogen bond connect the layers into a three-dimensional network.
Related literature
For general background on coordination polymers and open-framework materials, see: James (2003); Serre et al. (2004); Yaghi et al. (1998, 2003). For related structures, see: Evans & Lin (2001); Luo et al. (2004).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2007); cell SAINT (Bruker, 2007); 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
10.1107/S1600536808044206/hy2176sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808044206/hy2176Isup2.hkl
A mixture of AgNO3 (0.169 g, 1 mmol), perchloric acid (0.12 ml), nicotinic acid (0.123 g, 1 mmol) and H2O (10 ml) was placed in a 23 ml Teflon-lined reactor, which was heated to 433 K for 3 d and then cooled to room temperature at a rate of 10 K h-1. The crystals obtained were washed with water and dried in air.
H atoms on C atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C). H atoms on O atoms were located in difference Fourier maps and were fixed with O—H = 0.82 Å and Uiso(H) = 1.5Ueq(O). The highest residual electron density was found 1.31 Å from atom O7 and the deepest hole 0.46 Å from atom O7.
Data collection: APEX2 (Bruker, 2007); cell
SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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).Fig. 1. The structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. | |
Fig. 2. The layer in the title compound. Hydrogen bonds and weak Ag···O interactions are shown as dashed lines. |
[Ag(C6H5NO2)2]ClO4 | F(000) = 896 |
Mr = 453.54 | Dx = 1.985 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 5837 reflections |
a = 8.0139 (4) Å | θ = 2.8–27.9° |
b = 26.3288 (15) Å | µ = 1.55 mm−1 |
c = 7.6891 (4) Å | T = 273 K |
β = 110.728 (1)° | Block, colourless |
V = 1517.36 (14) Å3 | 0.29 × 0.25 × 0.21 mm |
Z = 4 |
Bruker APEXII CCD diffractometer | 2729 independent reflections |
Radiation source: fine-focus sealed tube | 2150 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
ϕ and ω scans | θmax = 25.2°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −8→9 |
Tmin = 0.649, Tmax = 0.731 | k = −29→31 |
7763 measured reflections | l = −9→8 |
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.123 | H-atom parameters constrained |
S = 0.87 | w = 1/[σ2(Fo2) + (0.0736P)2 + 4.5241P] where P = (Fo2 + 2Fc2)/3 |
2729 reflections | (Δ/σ)max = 0.001 |
219 parameters | Δρmax = 1.26 e Å−3 |
0 restraints | Δρmin = −0.57 e Å−3 |
[Ag(C6H5NO2)2]ClO4 | V = 1517.36 (14) Å3 |
Mr = 453.54 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.0139 (4) Å | µ = 1.55 mm−1 |
b = 26.3288 (15) Å | T = 273 K |
c = 7.6891 (4) Å | 0.29 × 0.25 × 0.21 mm |
β = 110.728 (1)° |
Bruker APEXII CCD diffractometer | 2729 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2150 reflections with I > 2σ(I) |
Tmin = 0.649, Tmax = 0.731 | Rint = 0.029 |
7763 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.123 | H-atom parameters constrained |
S = 0.87 | Δρmax = 1.26 e Å−3 |
2729 reflections | Δρmin = −0.57 e Å−3 |
219 parameters |
x | y | z | Uiso*/Ueq | ||
Ag1 | 0.40344 (6) | 0.612387 (13) | 0.34075 (6) | 0.05534 (19) | |
C1 | 0.3293 (6) | 0.72596 (17) | 0.4083 (7) | 0.0438 (11) | |
H1 | 0.2115 | 0.7150 | 0.3691 | 0.053* | |
Cl1 | 0.97387 (18) | 0.61558 (5) | 0.3633 (2) | 0.0544 (3) | |
N1 | 0.4208 (5) | 0.53278 (14) | 0.2719 (6) | 0.0457 (9) | |
O1 | 0.2535 (4) | 0.86018 (12) | 0.4508 (5) | 0.0488 (8) | |
C2 | 0.3650 (6) | 0.77700 (16) | 0.4460 (6) | 0.0367 (10) | |
N2 | 0.4580 (5) | 0.69166 (14) | 0.4261 (6) | 0.0437 (9) | |
O2 | 0.0616 (5) | 0.79535 (13) | 0.3776 (6) | 0.0596 (10) | |
H2 | −0.0120 | 0.8184 | 0.3499 | 0.089* | |
C3 | 0.2204 (6) | 0.81428 (17) | 0.4237 (7) | 0.0425 (11) | |
O3 | 0.0023 (4) | 0.43163 (13) | 0.1274 (6) | 0.0541 (9) | |
H3 | −0.0738 | 0.4093 | 0.0982 | 0.081* | |
C4 | 0.5421 (6) | 0.79317 (18) | 0.5073 (7) | 0.0466 (11) | |
H4 | 0.5706 | 0.8271 | 0.5356 | 0.056* | |
O4 | 0.1889 (5) | 0.36546 (12) | 0.1767 (5) | 0.0519 (9) | |
C5 | 0.6742 (6) | 0.75790 (19) | 0.5251 (7) | 0.0488 (12) | |
H5 | 0.7932 | 0.7678 | 0.5642 | 0.059* | |
O5 | 1.0454 (10) | 0.6352 (3) | 0.2338 (8) | 0.147 (3) | |
C6 | 0.6276 (6) | 0.70794 (18) | 0.4842 (7) | 0.0455 (11) | |
H6 | 0.7176 | 0.6843 | 0.4974 | 0.055* | |
O6 | 1.0605 (13) | 0.6412 (4) | 0.5267 (9) | 0.174 (4) | |
C7 | 0.2868 (6) | 0.49924 (17) | 0.2338 (7) | 0.0409 (10) | |
H7 | 0.1745 | 0.5107 | 0.2256 | 0.049* | |
O7 | 0.7884 (7) | 0.6209 (2) | 0.2885 (11) | 0.117 (2) | |
C8 | 0.3093 (6) | 0.44812 (16) | 0.2063 (6) | 0.0372 (10) | |
O8 | 1.0104 (10) | 0.5643 (3) | 0.3779 (16) | 0.187 (4) | |
C9 | 0.1598 (6) | 0.41126 (17) | 0.1687 (7) | 0.0409 (10) | |
C10 | 0.4758 (7) | 0.43088 (19) | 0.2185 (8) | 0.0500 (12) | |
H10 | 0.4948 | 0.3966 | 0.2025 | 0.060* | |
C11 | 0.6130 (7) | 0.4653 (2) | 0.2546 (8) | 0.0567 (14) | |
H11 | 0.7258 | 0.4547 | 0.2613 | 0.068* | |
C12 | 0.5813 (7) | 0.5153 (2) | 0.2807 (8) | 0.0534 (13) | |
H12 | 0.6751 | 0.5383 | 0.3056 | 0.064* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ag1 | 0.0591 (3) | 0.0284 (2) | 0.0765 (3) | 0.00062 (16) | 0.0214 (2) | −0.00512 (17) |
C1 | 0.039 (2) | 0.035 (2) | 0.055 (3) | −0.0009 (19) | 0.014 (2) | −0.005 (2) |
Cl1 | 0.0416 (7) | 0.0587 (8) | 0.0659 (8) | 0.0030 (6) | 0.0228 (6) | 0.0001 (6) |
N1 | 0.044 (2) | 0.033 (2) | 0.060 (3) | −0.0025 (17) | 0.0185 (19) | −0.0041 (18) |
O1 | 0.0469 (19) | 0.0275 (17) | 0.067 (2) | −0.0023 (14) | 0.0137 (17) | 0.0003 (15) |
C2 | 0.041 (2) | 0.030 (2) | 0.040 (2) | −0.0015 (18) | 0.0161 (19) | −0.0009 (18) |
N2 | 0.044 (2) | 0.032 (2) | 0.054 (2) | 0.0018 (17) | 0.0163 (18) | −0.0036 (17) |
O2 | 0.043 (2) | 0.0321 (18) | 0.100 (3) | 0.0010 (15) | 0.020 (2) | −0.0021 (18) |
C3 | 0.044 (3) | 0.034 (2) | 0.050 (3) | −0.003 (2) | 0.017 (2) | −0.002 (2) |
O3 | 0.0402 (19) | 0.0365 (18) | 0.084 (3) | −0.0042 (15) | 0.0195 (18) | −0.0055 (18) |
C4 | 0.047 (3) | 0.035 (2) | 0.054 (3) | −0.005 (2) | 0.014 (2) | 0.000 (2) |
O4 | 0.049 (2) | 0.0302 (18) | 0.074 (2) | 0.0013 (15) | 0.0181 (17) | 0.0021 (16) |
C5 | 0.038 (3) | 0.042 (3) | 0.065 (3) | −0.002 (2) | 0.016 (2) | −0.002 (2) |
O5 | 0.133 (5) | 0.226 (9) | 0.086 (4) | −0.095 (6) | 0.043 (4) | −0.031 (5) |
C6 | 0.042 (3) | 0.043 (3) | 0.051 (3) | 0.006 (2) | 0.016 (2) | 0.000 (2) |
O6 | 0.219 (9) | 0.219 (9) | 0.081 (4) | −0.109 (8) | 0.050 (5) | −0.050 (5) |
C7 | 0.036 (2) | 0.033 (2) | 0.051 (3) | 0.0015 (18) | 0.012 (2) | −0.0008 (19) |
O7 | 0.061 (3) | 0.086 (4) | 0.210 (7) | 0.007 (3) | 0.055 (4) | 0.005 (4) |
C8 | 0.038 (2) | 0.032 (2) | 0.041 (2) | 0.0006 (18) | 0.0116 (19) | −0.0027 (18) |
O8 | 0.118 (6) | 0.104 (5) | 0.323 (12) | 0.054 (4) | 0.057 (7) | −0.004 (7) |
C9 | 0.042 (3) | 0.031 (2) | 0.047 (3) | 0.0009 (19) | 0.013 (2) | −0.0031 (19) |
C10 | 0.052 (3) | 0.034 (3) | 0.064 (3) | 0.004 (2) | 0.021 (2) | −0.008 (2) |
C11 | 0.044 (3) | 0.051 (3) | 0.079 (4) | 0.001 (2) | 0.027 (3) | −0.010 (3) |
C12 | 0.043 (3) | 0.045 (3) | 0.075 (4) | −0.005 (2) | 0.024 (3) | −0.004 (3) |
Ag1—N1 | 2.178 (4) | O2—H2 | 0.8200 |
Ag1—N2 | 2.185 (4) | O3—C9 | 1.303 (6) |
Ag1—O1i | 2.899 (2) | O3—H3 | 0.8200 |
Ag1—O5ii | 2.757 (8) | C4—C5 | 1.378 (7) |
C1—N2 | 1.341 (6) | C4—H4 | 0.9300 |
C1—C2 | 1.383 (6) | O4—C9 | 1.226 (6) |
C1—H1 | 0.9300 | C5—C6 | 1.373 (7) |
Cl1—O8 | 1.378 (7) | C5—H5 | 0.9300 |
Cl1—O6 | 1.378 (6) | C6—H6 | 0.9300 |
Cl1—O7 | 1.398 (6) | C7—C8 | 1.384 (6) |
Cl1—O5 | 1.411 (6) | C7—H7 | 0.9300 |
N1—C7 | 1.341 (6) | C8—C10 | 1.381 (7) |
N1—C12 | 1.345 (6) | C8—C9 | 1.489 (6) |
O1—C3 | 1.239 (5) | C10—C11 | 1.375 (7) |
C2—C4 | 1.394 (6) | C10—H10 | 0.9300 |
C2—C3 | 1.482 (6) | C11—C12 | 1.370 (7) |
N2—C6 | 1.342 (6) | C11—H11 | 0.9300 |
O2—C3 | 1.294 (6) | C12—H12 | 0.9300 |
N1—Ag1—N2 | 165.65 (15) | C2—C4—H4 | 120.6 |
N2—C1—C2 | 122.6 (4) | C6—C5—C4 | 119.1 (5) |
N2—C1—H1 | 118.7 | C6—C5—H5 | 120.5 |
C2—C1—H1 | 118.7 | C4—C5—H5 | 120.5 |
O8—Cl1—O6 | 112.4 (6) | N2—C6—C5 | 122.9 (4) |
O8—Cl1—O7 | 107.2 (4) | N2—C6—H6 | 118.5 |
O6—Cl1—O7 | 116.4 (6) | C5—C6—H6 | 118.5 |
O8—Cl1—O5 | 106.8 (6) | N1—C7—C8 | 122.4 (4) |
O6—Cl1—O5 | 105.3 (4) | N1—C7—H7 | 118.8 |
O7—Cl1—O5 | 108.1 (5) | C8—C7—H7 | 118.8 |
C7—N1—C12 | 117.6 (4) | C10—C8—C7 | 119.0 (4) |
C7—N1—Ag1 | 124.9 (3) | C10—C8—C9 | 119.4 (4) |
C12—N1—Ag1 | 117.3 (3) | C7—C8—C9 | 121.6 (4) |
C1—C2—C4 | 118.5 (4) | O4—C9—O3 | 124.6 (4) |
C1—C2—C3 | 121.6 (4) | O4—C9—C8 | 120.4 (4) |
C4—C2—C3 | 119.9 (4) | O3—C9—C8 | 115.0 (4) |
C1—N2—C6 | 118.1 (4) | C11—C10—C8 | 118.8 (5) |
C1—N2—Ag1 | 123.2 (3) | C11—C10—H10 | 120.6 |
C6—N2—Ag1 | 118.5 (3) | C8—C10—H10 | 120.6 |
C3—O2—H2 | 109.5 | C12—C11—C10 | 119.1 (5) |
O1—C3—O2 | 123.6 (4) | C12—C11—H11 | 120.4 |
O1—C3—C2 | 120.9 (4) | C10—C11—H11 | 120.4 |
O2—C3—C2 | 115.4 (4) | N1—C12—C11 | 123.0 (5) |
C9—O3—H3 | 109.5 | N1—C12—H12 | 118.5 |
C5—C4—C2 | 118.8 (4) | C11—C12—H12 | 118.5 |
C5—C4—H4 | 120.6 |
Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x−1, y, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···O5ii | 0.93 | 2.51 | 3.244 (8) | 136 |
C4—H4···O7iii | 0.93 | 2.52 | 3.266 (8) | 139 |
C6—H6···O7 | 0.93 | 2.52 | 3.248 (8) | 136 |
C7—H7···O8ii | 0.93 | 2.49 | 3.287 (9) | 144 |
C12—H12···O7 | 0.93 | 2.38 | 3.228 (9) | 152 |
O2—H2···O4iv | 0.82 | 1.84 | 2.649 (5) | 169 |
O3—H3···O1v | 0.82 | 1.87 | 2.689 (5) | 175 |
Symmetry codes: (ii) x−1, y, z; (iii) x, −y+3/2, z+1/2; (iv) −x, y+1/2, −z+1/2; (v) −x, y−1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [Ag(C6H5NO2)2]ClO4 |
Mr | 453.54 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 273 |
a, b, c (Å) | 8.0139 (4), 26.3288 (15), 7.6891 (4) |
β (°) | 110.728 (1) |
V (Å3) | 1517.36 (14) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.55 |
Crystal size (mm) | 0.29 × 0.25 × 0.21 |
Data collection | |
Diffractometer | Bruker APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.649, 0.731 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7763, 2729, 2150 |
Rint | 0.029 |
(sin θ/λ)max (Å−1) | 0.599 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.123, 0.87 |
No. of reflections | 2729 |
No. of parameters | 219 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.26, −0.57 |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···O5i | 0.93 | 2.51 | 3.244 (8) | 136 |
C4—H4···O7ii | 0.93 | 2.52 | 3.266 (8) | 139 |
C6—H6···O7 | 0.93 | 2.52 | 3.248 (8) | 136 |
C7—H7···O8i | 0.93 | 2.49 | 3.287 (9) | 144 |
C12—H12···O7 | 0.93 | 2.38 | 3.228 (9) | 152 |
O2—H2···O4iii | 0.82 | 1.84 | 2.649 (5) | 169 |
O3—H3···O1iv | 0.82 | 1.87 | 2.689 (5) | 175 |
Symmetry codes: (i) x−1, y, z; (ii) x, −y+3/2, z+1/2; (iii) −x, y+1/2, −z+1/2; (iv) −x, y−1/2, −z+1/2. |
Acknowledgements
The authors kindly acknowledge Bijie University for supporting this work.
References
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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.
The use of multifunctional organic linker molecules in the preparation of coordination polymers and open-framework materials has led to the development of a rich field of chemistry owing to the potential applications of these materials in catalysis, separation, gas storage and molecular recognition (James, 2003; Serre et al., 2004; Yaghi et al., 1998, 2003). In our investigations we used nicotinic acid ligands for the preparation of new coordination polymers, because it can act as a multidentate ligand with versatile binding and coordination modes (Evans & Lin, 2001; Luo et al., 2004). In this paper, we report the crystal structure of the title compound, a new AgI complex obtained by the reaction of nicotinic acid, AgNO3 and perchloric acid in water.
As shown in Fig. 1, the title compound consists of a [Ag(C6H5NO2)2]+ cation and a perchlorate anion. The AgI atom exhibits a linear coordination geometry, defined by two N atoms from two pyridine-3-carboxylic acid ligands (Table 1). The complex cations are linked by hydrogen bonds between the carboxyl groups into a chain (Table 2). The chains are further connected by C—H···O hydrogen bonds involving C1, C6, C7 and C12 atoms and the perchlorate anions, and by a weak Ag1···O5(x-1, y, z) interaction [2.757 (8) Å] into a layer (Fig. 2). Another Ag1···O1(x, 3/2-y, z-1/2) interaction [2.899 (2) Å] and a C4—H4···O7(x, 3/2-y, 1/2+z) hydrogen bond connect the layers into a three-dimensional network.