catena Poly­[[aqua­nitritosilver(I)] μ 1,4 di­aza­bi­cyclo­[2,2,2]­octane κ2N:N′]

(1)metal-organic papers catena-Poly[[aquanitritosilver(I)]-l-1,4-diazabicyclo[2,2,2]octane-j2N:N0 ]. Acta Crystallographica Section E. Structure Reports Online ISSN 1600-5368. Zhong-Lu You,a,b Hai-Liang Zhua* and Wei-Sheng Liub a. Department of Chemistry, Fuyang Normal College, Fuyang Anhui 236041, People's Republic of China, and bDepartment of Chemistry, Lanzhou University, Lanzhou 730000, People's Republic of China Correspondence e-mail: hailiang_zhu@163.com. The title compound, [Ag(NO2)(C6H12N2)(H2O)]n, is a polymeric 1,4-diazabicyclo[2,2,2]octane±AgI complex. Each Ag atom is ®ve-coordinated by two N atoms from two different 1,4-diazabicyclo[2,2,2]octane ligands, two O atoms of one nitrite anion and another O atom of a coordinated water molecule, forming a severely distorted square-pyramidal coordination environment. In the crystal structure, molecules are connected by intermolecular OÐH  O hydrogen bonds, forming a three-dimensional network.. Received 13 October 2004 Accepted 21 October 2004 Online 6 November 2004. Comment Key indicators Single-crystal X-ray study T = 298 K Ê Mean (C±C) = 0.011 A R factor = 0.040 wR factor = 0.096 Data-to-parameter ratio = 11.9 For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.. Crystal engineering and the design of solid-state architectures of coordination polymers have become very attractive ®elds in recent years (Smith et al., 1996; Kristiansson, 2001; Wei et al., 1998; Zheng et al., 2001). Assembly of such extended supramolecular architectures by selecting the chemical structure of organic ligands and the coordination geometry of metal ions may yield a large number of new networks exhibiting interesting topologies and potential properties as new materials (Zhu et al., 2003; Zheng et al., 2003; Khlobystov et al., 2001). The primary reason for the interest in such complexes is their ability to afford functional solid materials with potentially controllable properties, as well as fascinating molecular structures. The recent development of supramolecular chemistry has made it possible to select building units for assembly into structures with speci®c network topologies (Nomiya et al., 2000). Crystal engineering of coordination polymeric networks based on multidentate ligands represents a growing area of coordination and supramolecular chemistry. We have focused our attention on the assembly of metal ions with bridging ligands, since they can adopt diverse coordination modes according to the different geometric needs of the metal ions. As reported previously, the bridging bidentate ligand 1,2diaminoethane gives two- or three-dimensional frameworks, depending on the metal ions and counter-anions (You, Yang et al., 2004; You & Zhu, 2004). We have now extended this work to include a 1,4-diazabicyclo[2,2,2]octane ligand in place of 1,2-diaminoethane.. # 2004 International Union of Crystallography Printed in Great Britain ± all rights reserved. m1744. You, Zhu and Liu. . [Ag(NO2)(C6H12N2)(H2O)]. doi: 10.1107/S1600536804026650. Acta Cryst. (2004). E60, m1744±m1746.

(2) metal-organic papers square pyramid or a distorted trigonal bipyramid can be answered by determining the structural index  (Addison et al., 1984). The value of  for Ag1 is 0.103, indicating that the coordination con®guration of the Ag atom in the complex is better described as distorted square pyramidal. In the crystal structure, the AgÐN bonds link the 1,4-diazabicyclo[2,2,2]octane molecules and the Ag atoms into a helical chain along the c axis. Adjacent chains are linked by intermolecular OÐH  O hydrogen bonds, forming a-three dimensional network (Table 2 and Fig. 2). Figure 1. The structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Unlabelled atoms are related by the symmetry code (ÿy, x, z ÿ 14).. Experimental 1,4-Diazabicyclo[2,2,2]octane (0.1 mmol, 11.2 mg) and AgNO2 (0.1 mmol, 15.4 mg) were dissolved in a 30% aqueous ammonia solution (10 ml). The mixture was stirred at room temperature for 20 min to give a colourless clear solution. The solution was kept in air and, after slow evaporation of the solvent over a period of a week, large colourless block-shaped crystals were formed at the bottom of the vessel. The crystals were isolated, washed three times with water and dried in a vacuum desiccator using anhydrous CaCl2 (yield 71.1%). Analysis found: C 25.2, H 5.0, N 14.9%; calculated for C6H14AgN3O3: C 25.4, H 5.0, N 14.8%. Crystal data. Figure 2. The crystal packing of (I), viewed along the b axis. Broken lines show intermolecular hydrogen bonds.. The title compound, (I), is a polymeric 1,4-diazabicyclo[2,2,2]octane±AgI complex (Fig. 1). The smallest repeat unit for the complex contains a 1,4-diazabicyclo[2,2,2]octane ligand, an AgI cation, a nitrite anion and a coordinated water molecule. The Ag atom is in a severely distorted squarepyramidal coordination environment, whose basal plane is composed of two N atoms from two different 1,4-diazabicyclo[2,2,2]octane ligands and two O atoms of a nitrite anion. The O atom of the coordinated water molecule occupies the apical position. The substantial distortion of the square pyramid is revealed by the bond angles between apical and basal donor atoms, showing an average deviation of 11.2 from the ideal 90 angle in a regular square pyramid. On the other hand, the bond angles between the donor atoms in basal positions deviate severely from the ideal 90 (Table 1). Thus, the coordination con®guration of the Ag atom is a severely distorted square pyramid. The bond angle N2iÐAg1ÐN1 of 121.09 (17) [symmetry code: (i) y ÿ 1, 1 ÿ x, 14 + z] is much larger than that of the O1ÐAg1ÐO2 angle, 47.95 (19) , which is due to the strain created by the four-membered chelate ring, viz. Ag1/O1/N3/O2. Atom Ag1 is displaced from the leastsquares plane de®ned by the basal donor atoms in the direcÊ. tion of the apical atom O3 by 0.413 (5) A The question of whether the coordination polyhedron around the Ag1 atom should be described as a distorted Acta Cryst. (2004). E60, m1744±m1746. [Ag(NO2)(C6H12N2)(H2O)] Mr = 284.07 Tetragonal, P43 Ê a = 6.706 (3) A Ê c = 21.834 (16) A Ê3 V = 981.9 (10) A Z=4 Dx = 1.922 Mg mÿ3. Mo K radiation Cell parameters from 4594 re¯ections  = 3.6±26.5  = 2.03 mmÿ1 T = 298 (2) K Block, colourless 0.48  0.43  0.37 mm. Data collection Bruker SMART CCD area-detector diffractometer ! scans Absorption correction: multi-scan (SADABS; Sheldrick, 1996) Tmin = 0.402, Tmax = 0.473 5148 measured re¯ections. 1478 independent re¯ections 1448 re¯ections with I > 2(I) Rint = 0.023 max = 25.0 h = ÿ7 ! 7 k = ÿ7 ! 7 l = ÿ25 ! 18. Refinement w = 1/[ 2(Fo2) + (0.0672P)2] where P = (Fo2 + 2Fc2)/3 (/)max < 0.001 Ê ÿ3 max = 0.52 e A Ê ÿ3 min = ÿ1.58 e A Absolute structure: Flack (1983), 590 Friedel pairs Flack parameter = 0.07 (7). Re®nement on F 2 R[F 2 > 2(F 2)] = 0.040 wR(F 2) = 0.096 S = 1.29 1478 re¯ections 124 parameters H atoms treated by a mixture of independent and constrained re®nement. Table 1. Ê ,  ). Selected geometric parameters (A Ag1ÐN2i Ag1ÐN1 Ag1ÐO1. 2.345 (5) 2.353 (5) 2.511 (5). N2iÐAg1ÐN1 N2iÐAg1ÐO1 N1ÐAg1ÐO1 N2iÐAg1ÐO3 N1ÐAg1ÐO3. Ag1ÐO3 Ag1ÐO2. 2.586 (5) 2.598 (6). O1ÐAg1ÐO3 N2iÐAg1ÐO2 N1ÐAg1ÐO2 O1ÐAg1ÐO2 O3ÐAg1ÐO2. 110.2 (2) 91.09 (19) 140.39 (17) 47.95 (19) 101.4 (2). [Ag(NO2)(C6H12N2)(H2O)]. m1745. 121.09 (17) 134.2 (2) 92.92 (17) 95.37 (18) 98.0 (2). Symmetry code: (i) y ÿ 1; 1 ÿ x; 14 ‡ z.. You, Zhu and Liu. .

(3) metal-organic papers The authors thank the Education Of®ce of Anhui Province, Peoples Republic of China, for research grant No. 2004kj300zd.. Table 2. Ê ,  ). Hydrogen-bonding geometry (A DÐH  A. DÐH. H  A. D  A. DÐH  A. O3ÐH1  O2ii O3ÐH2  O1iii. 0.84 (3) 0.83 (7). 2.06 (4) 2.08 (5). 2.899 (9) 2.854 (7). 176 (9) 154 (10). Symmetry codes: (ii) ÿy; x; z ÿ. 1 4;. (iii) x ÿ 1; y; z.. Water H atoms were located in a difference Fourier map and re®ned isotropically, with the OÐH and H  H distances restrained Ê , respectively. All remaining H atoms were to 0.84 (1) and 1.37 (2) A placed in geometrically idealized positions and constrained to ride on Ê and Uiso(H) = 1.2Ueq(C). An their parent atoms, with CÐH = 0.97 A Ê from atom unassigned maximum residual density was observed 1.0 A Ê from atom H3A. The minimum residual density was observed 0.2 A Ag1. Data collection: SMART (Bruker, 1998); cell re®nement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to re®ne structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.. m1746. You, Zhu and Liu. . [Ag(NO2)(C6H12N2)(H2O)]. References Addison, A. W., Rao, T. N., Reedijk, J., van Rijn, J. & Verschoor, G. C. (1984). J. Chem. Soc. Dalton Trans. pp. 1349±1356. Bruker (1998). SMART (Version 5.628), SAINT (Version 6.02) and SHELXTL (Version 5.1). Bruker AXS Inc., Madison, Wisconsin, USA. Flack, H. D. (1983). Acta Cryst. A39, 876±881. Kristiansson, O. (2001). Inorg. Chem. 40, 5058±5059. Khlobystov, A. N., Blake, A. J., Champness, N. R., Lemenovskii, D. A., Majouga, A. G., Zyk, N. V. & SchroÈder, M. (2001). Coord. Chem. Rev. 222, 155±192. Nomiya, K., Takahashi, S., Noguchi, R., Nemoto, S., Takayama, T. & Oda, M. (2000). Inorg. Chem. 39, 3301±3311. Sheldrick, G. M. (1996). SADABS. University of GoÈttingen, Germany. Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of GoÈttingen, Germany. Smith, G., Lynch, D. E. & Kennard, C. H. L. (1996). Inorg. Chem. 35, 2711± 2712. Wei, P., Mak, T. C. W. & Atwood, D. A. (1998). Inorg. Chem. 37, 2605±2607. You, Z.-L., Yang, L., Zou, Y., Zeng, W.-J., Liu, W.-S. & Zhu, H.-L. (2004). Acta Cryst. C60, m117±m118. You, Z.-L. & Zhu, H.-L. (2004). Acta Cryst. C60, m515±m516. Zheng, S.-L., Tong, M.-L., Zhu, H.-L. & Chen, X.-M. (2001). New J. Chem. 25, 1425±1429. Zheng, S.-L., Zhang, J.-P., Wong, W.-T. & Chen, X.-M. (2003). J. Am. Chem. Soc. 125, 6882±6883. Zhu, H.-L., Zhang, X.-M., Liu, X.-Y., Wang, X.-J., Liu, G.-F., Usman, A. & Fun, H.-K. (2003). Inorg. Chem. Commun. 6, 1113±1116.. Acta Cryst. (2004). E60, m1744±m1746.

(4) supporting information. supporting information Acta Cryst. (2004). E60, m1744–m1746. [https://doi.org/10.1107/S1600536804026650]. catena-Poly[[aquanitritosilver(I)]-µ-1,4-diazabicyclo[2,2,2]octane-κ2N:N′] Zhong-Lu You, Hai-Liang Zhu and Wei-Sheng Liu catena-Poly[[aquanitritosilver(I)]µ-1,4-diazabicyclo[2,2,2]octane-κ2N:N′] Crystal data [Ag(NO2)(C6H12N2)(H2O)] Mr = 284.07 Tetragonal, P43 Hall symbol: P 4cw a = 6.706 (3) Å c = 21.834 (16) Å V = 981.9 (10) Å3 Z=4 F(000) = 568. Dx = 1.922 Mg m−3 Mo Kα radiation, λ = 0.71073 Å Cell parameters from 4594 reflections θ = 3.6–26.5° µ = 2.03 mm−1 T = 298 K Block, colourless 0.48 × 0.43 × 0.37 mm. Data collection Bruker SMART CCD area-detector diffractometer Radiation source: fine-focus sealed tube Graphite monochromator ω scans Absorption correction: multi-scan (SADABS; Sheldrick, 1996) Tmin = 0.402, Tmax = 0.473. 5148 measured reflections 1478 independent reflections 1448 reflections with I > 2σ(I) Rint = 0.023 θmax = 25.0°, θmin = 3.0° h = −7→7 k = −7→7 l = −25→18. Refinement Refinement on F2 Least-squares matrix: full R[F2 > 2σ(F2)] = 0.040 wR(F2) = 0.096 S = 1.29 1478 reflections 124 parameters 4 restraints Primary atom site location: structure-invariant direct methods Secondary atom site location: difference Fourier map. Hydrogen site location: inferred from neighbouring sites H atoms treated by a mixture of independent and constrained refinement w = 1/[σ2(Fo2) + (0.0672P)2] where P = (Fo2 + 2Fc2)/3 (Δ/σ)max < 0.001 Δρmax = 0.52 e Å−3 Δρmin = −1.58 e Å−3 Absolute structure: Flack (1983), 590 Friedels Absolute structure parameter: 0.07 (7). 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.. Acta Cryst. (2004). E60, m1744–m1746. sup-1.

(5) supporting information 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). Ag1 O1 O2 O3 N1 N2 N3 C1 H1A H1B C2 H2A H2B C3 H3A H3B C4 H4A H4B C5 H5A H5B C6 H6A H6B H1 H2. x. y. z. Uiso*/Ueq. 0.16956 (6) 0.4885 (7) 0.3196 (9) −0.1153 (8) 0.2596 (7) 0.3631 (8) 0.4778 (9) 0.4736 (10) 0.5526 0.4956 0.5407 (9) 0.6101 0.6317 0.1411 (12) 0.1541 0.0012 0.2177 (12) 0.1060 0.2796 0.2290 (12) 0.0928 0.3173 0.2703 (11) 0.3589 0.1464 −0.147 (14) −0.215 (9). 0.52184 (6) 0.3271 (7) 0.2432 (9) 0.3321 (10) 0.7341 (7) 0.9721 (6) 0.2228 (10) 0.7860 (11) 0.6650 0.8607 0.9129 (11) 1.0312 0.8361 0.9238 (11) 0.9841 0.8949 1.0699 (10) 1.1177 1.1840 0.6403 (10) 0.5928 0.5265 0.7887 (10) 0.7284 0.8224 0.333 (18) 0.300 (16). 0.23199 (5) 0.2252 (3) 0.3006 (3) 0.1774 (3) 0.1508 (2) 0.0633 (3) 0.2716 (4) 0.1562 (4) 0.1582 0.1936 0.1002 (4) 0.1143 0.0750 0.1532 (4) 0.1934 0.1462 0.1037 (4) 0.0796 0.1233 0.0900 (3) 0.0869 0.0859 0.0382 (3) 0.0084 0.0178 0.1402 (12) 0.198 (4). 0.03857 (19) 0.0572 (13) 0.0668 (16) 0.0612 (15) 0.0292 (10) 0.0288 (11) 0.0499 (15) 0.0435 (15) 0.052* 0.052* 0.0436 (15) 0.052* 0.052* 0.0506 (18) 0.061* 0.061* 0.0463 (16) 0.056* 0.056* 0.0475 (17) 0.057* 0.057* 0.0443 (15) 0.053* 0.053* 0.080* 0.080*. Atomic displacement parameters (Å2). Ag1 O1 O2 O3 N1 N2 N3 C1 C2. U11. U22. U33. U12. U13. U23. 0.0407 (3) 0.054 (2) 0.068 (3) 0.044 (3) 0.036 (2) 0.039 (2) 0.052 (3) 0.042 (3) 0.044 (4). 0.0465 (3) 0.061 (3) 0.072 (3) 0.095 (4) 0.029 (2) 0.026 (2) 0.046 (3) 0.048 (3) 0.047 (4). 0.0285 (3) 0.057 (4) 0.060 (4) 0.045 (3) 0.022 (3) 0.021 (3) 0.052 (5) 0.040 (4) 0.040 (4). 0.00881 (16) 0.005 (2) 0.019 (3) −0.011 (3) 0.0027 (16) −0.0013 (16) 0.012 (2) −0.005 (3) −0.007 (3). 0.01154 (18) 0.015 (3) 0.023 (3) 0.004 (2) 0.0007 (18) 0.000 (2) −0.007 (3) −0.008 (3) −0.008 (3). 0.0105 (2) 0.015 (3) 0.017 (3) −0.016 (3) 0.0039 (19) 0.0052 (17) 0.009 (3) 0.018 (3) 0.013 (3). Acta Cryst. (2004). E60, m1744–m1746. sup-2.

(6) supporting information C3 C4 C5 C6. 0.061 (4) 0.062 (4) 0.069 (4) 0.059 (4). 0.048 (4) 0.039 (3) 0.037 (3) 0.041 (3). 0.043 (5) 0.037 (4) 0.037 (4) 0.033 (4). 0.015 (3) 0.013 (3) −0.017 (3) −0.014 (3). 0.012 (3) 0.016 (3) 0.001 (3) −0.005 (3). 0.014 (3) 0.010 (3) −0.001 (3) 0.002 (3). Geometric parameters (Å, º) Ag1—N2i Ag1—N1 Ag1—O1 Ag1—O3 Ag1—O2 O1—N3 O2—N3 O3—H1 O3—H2 N1—C1 N1—C5 N1—C3 N2—C4 N2—C6 N2—C2 N2—Ag1ii. 2.345 (5) 2.353 (5) 2.511 (5) 2.586 (5) 2.598 (6) 1.235 (10) 1.243 (9) 0.84 (3) 0.83 (7) 1.481 (8) 1.482 (9) 1.501 (8) 1.470 (8) 1.483 (8) 1.491 (8) 2.345 (5). C1—C2 C1—H1A C1—H1B C2—H2A C2—H2B C3—C4 C3—H3A C3—H3B C4—H4A C4—H4B C5—C6 C5—H5A C5—H5B C6—H6A C6—H6B. 1.556 (10) 0.9700 0.9700 0.9700 0.9700 1.547 (10) 0.9700 0.9700 0.9700 0.9700 1.532 (9) 0.9700 0.9700 0.9700 0.9700. N2i—Ag1—N1 N2i—Ag1—O1 N1—Ag1—O1 N2i—Ag1—O3 N1—Ag1—O3 O1—Ag1—O3 N2i—Ag1—O2 N1—Ag1—O2 O1—Ag1—O2 O3—Ag1—O2 N3—O1—Ag1 N3—O2—Ag1 Ag1—O3—H1 Ag1—O3—H2 H1—O3—H2 C1—N1—C5 C1—N1—C3 C5—N1—C3 C1—N1—Ag1 C5—N1—Ag1 C3—N1—Ag1 C4—N2—C6 C4—N2—C2 C6—N2—C2. 121.09 (17) 134.2 (2) 92.92 (17) 95.37 (18) 98.0 (2) 110.2 (2) 91.09 (19) 140.39 (17) 47.95 (19) 101.4 (2) 101.3 (4) 96.7 (5) 129 (7) 118 (7) 109 (8) 107.8 (5) 108.1 (5) 108.5 (6) 109.3 (4) 112.5 (4) 110.5 (4) 108.2 (5) 108.9 (6) 108.3 (5). C2—C1—H1B H1A—C1—H1B N2—C2—C1 N2—C2—H2A C1—C2—H2A N2—C2—H2B C1—C2—H2B H2A—C2—H2B N1—C3—C4 N1—C3—H3A C4—C3—H3A N1—C3—H3B C4—C3—H3B H3A—C3—H3B N2—C4—C3 N2—C4—H4A C3—C4—H4A N2—C4—H4B C3—C4—H4B H4A—C4—H4B N1—C5—C6 N1—C5—H5A C6—C5—H5A N1—C5—H5B. 109.6 108.1 109.8 (5) 109.7 109.7 109.7 109.7 108.2 109.6 (6) 109.7 109.7 109.7 109.7 108.2 110.9 (5) 109.5 109.5 109.5 109.5 108.0 111.1 (5) 109.4 109.4 109.4. Acta Cryst. (2004). E60, m1744–m1746. sup-3.

(7) supporting information C4—N2—Ag1ii C6—N2—Ag1ii C2—N2—Ag1ii O1—N3—O2 N1—C1—C2 N1—C1—H1A C2—C1—H1A N1—C1—H1B. 114.9 (4) 109.1 (4) 107.3 (4) 113.9 (5) 110.2 (5) 109.6 109.6 109.6. C6—C5—H5B H5A—C5—H5B N2—C6—C5 N2—C6—H6A C5—C6—H6A N2—C6—H6B C5—C6—H6B H6A—C6—H6B. 109.4 108.0 110.0 (6) 109.7 109.7 109.7 109.7 108.2. Symmetry codes: (i) y−1, −x+1, z+1/4; (ii) −y+1, x+1, z−1/4.. Hydrogen-bond geometry (Å, º) D—H···A iii. O3—H1···O2 O3—H2···O1iv. D—H. H···A. D···A. D—H···A. 0.84 (3) 0.83 (7). 2.06 (4) 2.08 (5). 2.899 (9) 2.854 (7). 176 (9) 154 (10). Symmetry codes: (iii) −y, x, z−1/4; (iv) x−1, y, z.. Acta Cryst. (2004). E60, m1744–m1746. sup-4.

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