metal-organic papers
Acta Cryst. (2007). E63, m1063–m1065 doi:10.1107/S1600536807010835 Qu and Wu � [Ag(C6H12N2)](C7H3N2O7) m1063
Acta Crystallographica Section E
Structure ReportsOnline
ISSN 1600-5368
The infinite one-dimensional chain polymercatena-poly[[silver(I)-l-1,4-diazabicyclo[2.2.2]-octane-j2N:N000] 2-hydroxy-3,5-dinitrobenzoate]]
Yang Qu* and Jin Wu
Institute of Biochemistry, Department of Chem-
istry, Huazhong Agricultural University, Wuhan,
430070, People’s Republic of China
Correspondence e-mail: [email protected]
Key indicators
Single-crystal X-ray study
T = 293 K
Mean �(C–C) = 0.005 A
H-atom completeness 81%
Disorder in solvent or counterion
R factor = 0.032
wR factor = 0.087
Data-to-parameter ratio = 8.2
For details of how these key indicators were
automatically derived from the article, see
http://journals.iucr.org/e.
Received 15 February 2007
Accepted 7 March 2007
# 2007 International Union of Crystallography
All rights reserved
In the title compound, {[Ag(C6H12N2)](C7H3N2O7)}n, the Ag
atom is coordinated by two N atoms from the two symmetry-
related 1,4-diazabicyclo[2.2.2]octane ligands, giving linear
polymeric chains with a [–silver–ligand–] backbone running
parallel to the c direction. In the crystal packing, the polymeric
chains are interconnected by weak Ag� � �Onitro van der Waals
forces, resulting in a three-dimensional supramolecular
network in the solid.
Comment
Crystal engineering of coordination polymers has attracted
great attention in recent years owing to their potential as
functional materials as well as their interesting compositions
and topologies (Yaghi et al., 1995; Stumpt et al., 1993). Our
study of the crystal structures of metal–triethylenediamine
coordination concerns the molecular factors that determine
their network structure frameworks (Qu et al., 2005).
Triethylenediamine, a bidentate ligand that can coordinate to
metal ions via two N atoms, has a very versatile coordination
behavior since it can form bridges between metallic centers,
generating varied and sometimes surprising molecular archi-
tectures (Zhu et al., 2003).
Here we report the preparation and crystal structure of
[Ag(dabco)2](C7H3N2O7) (dabco is 1,4-diazabicyclo[2.2.2]-
octane), (I). Complex (I) is a polymeric AgI complex.
O1,O2,N2,C4 lie on sites of symmetry m; Ag1, N1 lie on sites
of symmetry 3m. In the crystal structure of (I), the smallest
repeat unit contains an [Ag-(dabco)2]+ cation and a 3,5-dini-
trosalicylate counter-ion, as shown in Fig. 1. The Ag atom in
(I) is coordinated by two N atoms from two different dabco
ligands in a linear geometry [N1—Ag—N1A = 180�; N1A
symmetry code: �y, �x, 12 � z]. The Ag—N bond (Table 1) is
comparable to those [2.186 (4)–2.199 (2) A] in related struc-
tures (Tong et al., 1998; Tong & Chen, 2000). Orientational
disorder is observed in the 3,5-dinitrosalicylate anion. The –
NO2 and –CO2 groups cannot be distinguished in the crystal
structure. The linear N1—Ag—N1A formation gives rise to a
linear polymer of the title complex, running parallel to the c
direction and having a [–silver–(dabco)]n backbone, resulting
in a polymeric chain (Fig. 2). Adjacent [Ag(dabco)2]+ cations
are interlinked through weak Ag� � �O(anion) coordination
[mean Ag� � �O(3,5-dinitrosalicylate) = 3.174 (2) A]. A three-
dimensional network structure is formed via weak Ag� � �O and
Ag� � �N interactions.
Experimental
All reagents and solvents were used as obtained without further
purification. AgO (1 mmol, 124 mg), 3,5-dinitrosalicylic acid (1 mmol,
211 mg) and 1,4-diazabicyclo[2.2.2]octane (1 mmol, 112 mg) were
dissolved in an ammonia solution (10 ml, 30%), and the mixture was
stirred for about 20 min at room temperature. The resulting clear
solution was kept in air and after slow evaporation of the solvent over
a period of a week, large colorless crystals of (I) 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
53%). Elemental analysis found: C 35.12, H 3.03, N 12.49%; calcu-
lated for C13H15AgN4O7: C 34.92, H 3.38, N 12.53%.
Crystal data
[Ag(C6H12N2)](C7H3N2O7)Mr = 447Hexagonal, P63=mmca = 11.1991 (16) Ac = 6.9696 (14) AV = 757.0 (2) A3
Z = 2Mo K� radiation� = 1.38 mm�1
T = 293 (2) K0.51 � 0.30 � 0.26 mm
Data collection
Siemens SMART CCD area-detector diffractometer
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)Tmin = 0.600, Tmax = 0.700
3755 measured reflections288 independent reflections279 reflections with I > 2�(I)Rint = 0.023
Refinement
R[F 2 > 2�(F 2)] = 0.032wR(F 2) = 0.087S = 1.00288 reflections
35 parametersH-atom parameters constrained��max = 0.54 e A�3
��min = �0.38 e A�3
Table 1Selected geometric parameters (A, �).
Ag1—N1 2.190 (6)N1—C1 1.485 (4)N2—O2 1.235 (5)N2—C3 1.473 (7)
O1—C2 1.160 (11)C1—C1ii 1.541 (8)C2—C3 1.400 (4)
N1i—Ag1—N1 180C1iii—N1—C1 108.3 (3)C1—N1—Ag1 110.7 (2)
O2—N2—C3 120.3 (3)O1—C2—C3 121.3 (3)C2—C3—N2 118.7 (3)
Symmetry codes: (i) x; y;�z þ 52; (ii) x; y;�zþ 3
2; (iii) �xþ y;�xþ 1; z.
The H atoms bonded to atom C1 were placed in calculated posi-
tions, with a C—H distance of 0.97 A and Uiso(H) values of 1.2 times
Ueq of the parent atom. The H atom of the OH group was not
included because of its orientational disorder. Atoms C2 and N2
atoms share the same site, with 1:2 occupancy.
Data collection: SMART (Siemens, 1996); cell refinement: SAINT
(Siemens, 1996); data reduction: SAINT; program(s) used to solve
structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine
metal-organic papers
m1064 Qu and Wu � [Ag(C6H12N2)](C7H3N2O7) Acta Cryst. (2007). E63, m1063–m1065
Figure 2Crystal packing of (I), viewed along the c axis. The dashed lines showweak Ag� � �O short contacts.
Figure 1A fragment of the polymeric structure of the title compound.Displacement ellipsoids for non-H atoms are drawn at the 30%probability level. [Symmetry codes: (A) �y, x � y, z; (B) �x + y, �x, z;(C) �x, �y, z + 1
2; (D) y, �x + y, z + 12; (E) x � y, x, z + 1
2; (F) �y, �x, z;(G) �x + y, y, z; (H) x, x � y, z.]
structure: SHELXL97 (Sheldrick, 1997); molecular graphics:
SHELXTL (Bruker, 1997); software used to prepare material for
publication: SHELXTL.
References
Bruker (1997). SHELXTL. Version 5.1. Bruker AXS Inc., Madison,Wisconsin, USA.
Qu, Y., Liu, Z.-D., Tan, M.-Y. & Zhu, H.-L. (2005). Acta Cryst. E61, m420–m422.
Sheldrick, G. M. (1996). SADABS. University of Gottingen, Germany.
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University ofGottingen, Germany.
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Systems Inc.,Madison, Wisconsin, USA.
Stumpt, H. O., Pei, L. Y., Grandjean, D. & Kahn, O. (1993). Science, 261, 447–449.
Tong, M.-L. & Chen, X.-M. (2000). Acta Cryst. C56, 1075–1076.Tong, M.-L., Chen, X.-M., Ye, B.-H. & Ng, S. W. (1998). Inorg. Chem. 37, 5278–
5281.Yaghi, O. M., Li, G. & Li, H. (1995). Nature (London), 378, 703–706.Zhu, H. L., Zhang, X. M., Liu, G. F. & Wang, D. Q. (2003). Z. Anorg. Allg.
Chem. 629, 1059–1062.
metal-organic papers
Acta Cryst. (2007). E63, m1063–m1065 Qu and Wu � [Ag(C6H12N2)](C7H3N2O7) m1065
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