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1 metal-organic compounds Acta Crystallographica Section E Structure Reports Online ISSN Diaquabis{4-[(pyridin-2-yl)methylideneamino]benzenesulfonato-j 2 N,N 0 }- nickel(ii) tetrahydrate Chao-Zhu Li and Xue-Ren Huang* College of Chemistry and Chemical Engineering, Qinzhou University, Qinzhou, Guangxi , People s Republic of China Correspondence @qq.com Received 4 May 2012; accepted 16 May 2012 Key indicators: single-crystal X-ray study; T = 296 K; mean (C C) = Å; R factor = 0.034; wr factor = 0.100; data-to-parameter ratio = Experimental Crystal data [Ni(C 12 H 9 N 2 O 3 S) 2 (H 2 O) 2 ]4H 2 O M r = Orthorhombic, Pna2 1 a = (2) Å b = (18) Å c = (3) Å Data collection Bruker SMART CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2000) T min = 0.821, T max = Refinement R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections 388 parameters 1 restraint V = (8) Å 3 Z =4 Mo K radiation = 0.85 mm 1 T = 296 K mm measured reflections 5315 independent reflections 4983 reflections with I > 2(I) R int = H-atom parameters constrained max = 0.44 e Å 3 min = 0.20 e Å 3 Absolute structure: Flack (1983), 2540 Friedel pairs Flack parameter: 0.00 (1) In the title complex, [Ni(C 12 H 9 N 2 O 3 S) 2 (H 2 O) 2 ]4H 2 O, the Ni II ion is coordinated by four N atoms from two bidentate chelating 4-[(pyridin-2-yl)methylideneamino]benzenesulfonate ligands and two O atoms from cis-related water molecules in a slightly distorted octahedral environment [Ni N = (3) (3) Å and Ni O = (2) and (3) Å]. In the crystal, the coordinated water molecules and the four water molecules of solvation are involved in intermolecular O HO hydrogen-bonding interactions with water and sulfonate O-atom acceptors, giving a threedimensional framework structure. Related literature For the synthesis of the ligand, see: Casella & Gullotti (1981). For the synthesis, structures and applications of similar complexes, see: Zhang et al. (2007, 2008). For the structures of the mainly tridentate complexes with the title ligand and similar ligands, see: Correia et al. (2003); Jiang et al. (2006); Ou-Yang et al. (2008); Li et al. (2006); Huang et al. (2009). Table 1 Hydrogen-bond geometry (Å, ). D HA D H HA DA D HA O1 H1O4 i (4) 166 O1 H1AO7 ii (4) 156 O2 H2AO1W (4) 159 O2 H2BO3W iii (4) 171 O1W H1WAO4W (5) 156 O1W H1WBO2W iv (5) 167 O2W H2WAO3 v (5) 137 O2W H2WBO7 vi (5) 125 O3W H3WBO6 v (6) 160 O3W H3WAO5 vii (5) 152 O4W H4WBO8 vi (5) 136 O4W H4WAO5 viii (5) 169 Symmetry codes: (i) x 1 2 ; y þ 5 2 ; z; (ii) x; y þ 2; z 1 2 ; (iii) x 1; y þ 1; z; (iv) x; y þ 1; z; (v) x þ 1; y þ 1; z 1 2 ; (vi) x; y þ 1; z 1 2 ; (vii) x; y 1; z; (viii) x 1 2 ; y þ 3 2 ; z. Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); 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. This work was funded by the Guangxi Science Foundation and Qinzhou University Science Foundation and the Guangxi Zhuang Autonomous Region of the People s Republic of China (grant Nos. 2010GXNSFA013017, 2010GXNSFA and 2011XJKY-14B). Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZS2208). doi: /s Li and Huang m809

2 metal-organic compounds References Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Casella, L. & Gullotti, M. (1981). J. Am. Chem. Soc. 103, Correia, V. R., Bortoluzzi, A. J., Neves, A., Joussef, A. C., Vieira, M. G. M. & Batista, S. C. (2003). Acta Cryst. E59, m464 m466. Flack, H. D. (1983). Acta Cryst. A39, Huang, X.-R., Ou-Yang, M., Yang, G.-G., Meng, X.-J. & Jiang, Y.-M. (2009). Acta Cryst. E65, m1465. Jiang, Y.-M., Li, J.-M., Xie, F.-Q. & Wang, Y.-F. (2006). Chin. J. Struct. Chem. 25, Li, J.-X., Jiang, Y.-M. & Li, H.-Y. (2006). Acta Cryst. E62, m2984 m2986. Ou-Yang, M., Huang, X.-R., Zhang, Y.-L. & Jiang, Y.-M. (2008). Acta Cryst. E64, m1461. Sheldrick, G. M. (2008). Acta Cryst. A64, Zhang, S.-H., Jiang, Y.-M. & Liu, Z.-M. (2008). J. Coord. Chem. 61, Zhang, S.-H., Li, G.-Z., Zhong, F. & Feng, X.-Z. (2007). Chin. J. Struct. Chem. 26, m810 Li and Huang [Ni(C 12 H 9 N 2 O 3 S) 2 (H 2 O) 2 ]4H 2 O

3 [doi: /s ] Diaquabis{4-[(pyridin-2-yl)methylideneamino]benzenesulfonatoκ 2 N,N }nickel(ii) tetrahydrate Chao-Zhu Li and Xue-Ren Huang S1. Comment The design and control of supramolecular coordination complex networks in which both coordinate bonds and hydrogen bonds take part in the molecular self-assenbly, have recently attracted increasing interest. Schiff base complexes that contain both sulfur and amino acid functionalities have also received much attention due to their potential application in pharmacy (Jiang et al., 2006; Zhang et al., 2007, 2008). We report here the synthesis and the stucture of the mononuclear Ni II complex with the potentially tridentate monoanionic ligand from the acid (4-pyridylmethylimine)benzenesulfonic acid (BfbaH), the title complex [Ni(C 12 H 9 N 2 O 3 S) 2 (H 2 O) 2 ]. 4H 2 O. Other complexes with this ligand or similar ligands in the N,N,O-tridentate mode are known (Correia et al., 2003; Li et al., 2006; Huang et al., 2009; Ou-Yang et al., 2008). The asymmetric unit of the title complex (Fig. 1) comprises a Ni 2+ cation, coordinated by four N atoms from two bidentate Bfba ligands and two O atoms from cis-related water molecules in a slightly distorted octahedral environment [Ni N, (3) (3) Å; Ni O, (3), (3) Å], together with four water molecules of solvation. The two ligands are conformationally different [dihedral angles between the pyridine and benzene rings in each: (18) and 43.2 (2) ]. In the crystal structure, the coordinated water molecules and the water molecules of solvation are involved in intermolecular O H O hydrogen-bonding interactions with water and sulfonate O-atom acceptors (Table 1) giving a three-dimensional framework structure (Fig. 2). S2. Experimental The potassium salt of (4-pyridylmethylimine)benzenesulfonic acid (BfbaK) was synthesized according to the literature method (Casella & Gullotti, 1981). To prepare the title complex, the ligand BfbaK (1 mmol) was dissolved in methanol (10 ml) at 333 K and an aqueous solution (10 ml) containing Ni(AcO) 2. 4H 2 O (0.5 mmol) was added. The resulting solution was stirred at 333 K for 4 h, then cooled to room temperature and filtered. Blue crystals of the title complex suitable for X-ray diffraction were obtained by slow evaporation of this solution over a period of several days (yield 50%). S3. Refinement All H-atoms were placed in calculated positions with O H = Å and C H = 0.93 Å and were allowed to ride in the refinement, with U</> iso (H) = 1.2U eq (C) or 1.5U eq (O). sup-1

4 Figure 1 The molecular structure of the title complex, showing the atom-numbering scheme. All H atoms have been omitted for clarity. Figure 2 The packing of the title complex, showing the two-dimensional sheet structure in the ac plane. sup-2

5 Diaquabis{4-[(pyridin-2-yl)methylideneamino]benzenesulfonato- κ 2 N,N }nickel(ii) tetrahydrate Crystal data [Ni(C 12 H 9 N 2 O 3 S) 2 (H 2 O) 2 ] 4H 2 O M r = Orthorhombic, Pna2 1 Hall symbol: P 2c -2n a = (2) Å b = (18) Å c = (3) Å V = (8) Å 3 Z = 4 Data collection Bruker SMART CCD area-detector diffractometer Radiation source: fine-focus sealed tube Graphite monochromator φ and ω scans Absorption correction: multi-scan (SADABS; Bruker, 2000) T min = 0.821, T max = Refinement Refinement on F 2 Least-squares matrix: full R[F 2 > 2σ(F 2 )] = wr(f 2 ) = S = reflections 388 parameters 1 restraint Primary atom site location: structure-invariant direct methods Secondary atom site location: difference Fourier map F(000) = 1432 D x = Mg m 3 Mo Kα radiation, λ = Å Cell parameters from 5315 reflections θ = µ = 0.85 mm 1 T = 296 K Prism, blue mm measured reflections 5315 independent reflections 4983 reflections with I > 2σ(I) R int = θ max = 25.1, θ min = 2.1 h = k = l = Hydrogen site location: inferred from neighbouring sites H-atom parameters constrained w = 1/[σ 2 (F o2 ) + (0.0792P) P] where P = (F o 2 + 2F c2 )/3 (Δ/σ) max = Δρ max = 0.44 e Å 3 Δρ min = 0.20 e Å 3 Absolute structure: Flack (1983), 2540 Friedel pairs Absolute structure parameter: 0.00 (1) 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. Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wr and goodness of fit S are based on F 2, conventional R-factors R are based on F, with F set to zero for negative F 2. The threshold expression of F 2 > σ(f 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 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 (Å 2 ) x y z U iso */U eq Ni (2) (3) (2) (11) S (6) (7) (5) (19) S (7) (8) (5) (2) sup-3

6 C (2) (3) (18) (7) C (3) (3) (19) (8) H * C (3) (3) (2) (8) H * C (3) (3) (18) (7) C (3) (4) (19) (9) H * C (3) (4) (2) (9) H * C (3) (3) (2) (7) H * C (2) (3) (19) (7) C (3) (4) (2) (9) H * C (3) (4) (2) (12) H * C (3) (4) (2) (11) H * C (3) (3) (2) (8) H * C (2) (3) (19) (8) H * C (3) (3) (2) (8) H * C (2) (3) (18) (7) C (2) (3) (2) (7) H * C (2) (3) (19) (7) H * C (2) (3) (18) (6) C (2) (3) (19) (8) H * C (2) (3) (2) (8) C (3) (6) (3) (16) H * C (3) (6) (3) (16) H * C (3) (4) (2) (10) H * C (2) (3) (2) (8) H * N (18) (2) (15) (6) N (16) (2) (15) (6) N (17) (2) (15) (6) N (18) (2) (14) (6) O (18) (2) (13) (5) H1A * sup-4

7 H * O (18) (2) (14) (6) H2B * H2A * O (19) (2) (16) (6) O (18) (2) (19) (7) O (2) (3) (17) (8) O (2) (3) (16) (9) O (2) (3) (17) (8) O (3) (3) (19) (12) O1W (2) (3) (17) (8) H1WA * H1WB * O2W (3) (3) (2) (10) H2WA * H2WB * O4W (3) (3) (2) (10) H4WB * H4WA * O3W (2) (4) (2) (13) H3WB * H3WA * Atomic displacement parameters (Å 2 ) U 11 U 22 U 33 U 12 U 13 U 23 Ni (19) (2) (2) (14) (17) (19) S (4) (4) (4) (3) (4) (4) S (5) (5) (4) (4) (4) (4) C (17) (16) (18) (13) (14) (13) C (18) (2) (18) (16) (14) (15) C (17) (2) (19) (16) (15) (16) C (18) (17) (17) (15) (14) (13) C (2) (2) (19) (17) (15) (16) C (17) (2) (2) (16) (15) (17) C (17) (16) (18) (14) (15) (15) C (16) (18) (16) (14) (14) (14) C (2) (2) (2) (18) (18) (19) C (2) (3) (3) (2) (2) (2) C (2) (3) (2) (2) (17) (2) C (19) (2) (2) (15) (15) (15) C (19) (2) (19) (14) (15) (15) C (18) (2) (2) (15) (15) (15) C (16) (16) (19) (13) (13) (14) C (14) (18) (16) (12) (15) (17) C (14) (18) (17) (12) (14) (15) C (14) (16) (17) (13) (13) (13) C (16) (2) (18) (15) (13) (15) sup-5

8 C (17) (2) (18) (15) (14) (15) C (2) (5) (2) (2) (18) (3) C (2) (5) (3) (3) (2) (3) C (18) (3) (2) (16) (17) (2) C (16) (18) (2) (14) (15) (15) N (14) (13) (15) (10) (10) (11) N (12) (15) (15) (10) (10) (11) N (12) (14) (14) (10) (11) (11) N (13) (14) (15) (10) (11) (11) O (13) (12) (13) (10) (11) (10) O (13) (16) (15) (11) (11) (12) O (13) (15) (17) (10) (11) (12) O (12) (15) (2) (11) (14) (16) O (17) (2) (17) (15) (14) (17) O (2) (3) (16) (2) (14) (17) O (18) (2) (18) (15) (15) (16) O (3) (2) (2) (18) (2) (16) O1W (17) (18) (2) (14) (14) (15) O2W (3) (2) (2) (19) (17) (18) O4W (3) (2) (2) (18) (19) (18) O3W (19) (3) (3) (2) (19) (3) Geometric parameters (Å, º) Ni1 N (3) C12 H Ni1 O (2) C13 C (5) Ni1 O (3) C13 C (5) Ni1 N (3) C13 H Ni1 N (3) C14 C (5) Ni1 N (3) C14 H S1 O (3) C15 C (5) S1 O (3) C16 C (4) S1 O (3) C16 H S1 C (3) C17 C (5) S2 O (3) C17 H S2 O (3) C18 N (4) S2 O (3) C19 N (5) S2 C (3) C19 C (5) C1 C (5) C19 H C1 C (5) C20 N (5) C1 N (4) C20 C (6) C2 C (5) C21 C (6) C2 H C21 H C3 C (5) C22 C (6) C3 H C22 H C4 C (5) C23 C (5) C5 C (5) C23 H C5 H C24 N (4) sup-6

9 C6 H C24 H C7 N (4) O1 H1A C7 C (5) O1 H C7 H O2 H2B C8 N (4) O2 H2A C8 C (5) O1W H1WA C9 C (6) O1W H1WB C9 H O2W H2WA C10 C (6) O2W H2WB C10 H O4W H4WB C11 C (6) O4W H4WA C11 H O3W H3WB C12 N (4) O3W H3WA N2 Ni1 O (10) N2 C12 H N2 Ni1 O (10) C11 C12 H O1 Ni1 O (10) C14 C13 C (3) N2 Ni1 N (11) C14 C13 H O1 Ni1 N (10) C18 C13 H O2 Ni1 N (11) C15 C14 C (3) N2 Ni1 N (11) C15 C14 H O1 Ni1 N (10) C13 C14 H O2 Ni1 N (10) C14 C15 C (3) N4 Ni1 N (11) C14 C15 S (3) N2 Ni1 N (10) C16 C15 S (3) O1 Ni1 N (10) C17 C16 C (3) O2 Ni1 N (11) C17 C16 H N4 Ni1 N (10) C15 C16 H N1 Ni1 N (11) C16 C17 C (3) O5 S1 O (17) C16 C17 H O5 S1 O (2) C18 C17 H O3 S1 O (18) C13 C18 C (3) O5 S1 C (18) C13 C18 N (3) O3 S1 C (16) C17 C18 N (3) O4 S1 C (15) N3 C19 C (3) O7 S2 O (2) N3 C19 H O7 S2 O (2) C20 C19 H O8 S2 O (2) N4 C20 C (3) O7 S2 C (17) N4 C20 C (3) O8 S2 C (18) C21 C20 C (3) O6 S2 C (17) C20 C21 C (4) C6 C1 C (3) C20 C21 H C6 C1 N (3) C22 C21 H C2 C1 N (3) C23 C22 C (4) C3 C2 C (3) C23 C22 H C3 C2 H C21 C22 H C1 C2 H C22 C23 C (3) C2 C3 C (3) C22 C23 H sup-7

10 C2 C3 H C24 C23 H C4 C3 H N4 C24 C (3) C5 C4 C (3) N4 C24 H C5 C4 S (3) C23 C24 H C3 C4 S (3) C7 N1 C (3) C4 C5 C (3) C7 N1 Ni (2) C4 C5 H C1 N1 Ni (2) C6 C5 H C12 N2 C (3) C1 C6 C (3) C12 N2 Ni (2) C1 C6 H C8 N2 Ni (2) C5 C6 H C19 N3 C (3) N1 C7 C (3) C19 N3 Ni (2) N1 C7 H C18 N3 Ni (2) C8 C7 H C20 N4 C (3) N2 C8 C (3) C20 N4 Ni (2) N2 C8 C (3) C24 N4 Ni (2) C9 C8 C (3) Ni1 O1 H1A C10 C9 C (4) Ni1 O1 H C10 C9 H H1A O1 H C8 C9 H Ni1 O2 H2B C9 C10 C (4) Ni1 O2 H2A C9 C10 H H2B O2 H2A C11 C10 H H1WA O1W H1WB C10 C11 C (4) H2WA O2W H2WB C10 C11 H H4WB O4W H4WA C12 C11 H H3WB O3W H3WA N2 C12 C (3) Hydrogen-bond geometry (Å, º) D H A D H H A D A D H A O1 H1 O4 i (4) 166 O1 H1A O7 ii (4) 156 O2 H2A O1W (4) 159 O2 H2B O3W iii (4) 171 O1W H1WA O4W (5) 156 O1W H1WB O2W iv (5) 167 O2W H2WA O3 v (5) 137 O2W H2WB O7 vi (5) 125 O3W H3WB O6 v (6) 160 O3W H3WA O5 vii (5) 152 O4W H4WB O8 vi (5) 136 O4W H4WA O5 viii (5) 169 Symmetry codes: (i) x 1/2, y+5/2, z; (ii) x, y+2, z 1/2; (iii) x 1, y+1, z; (iv) x, y+1, z; (v) x+1, y+1, z 1/2; (vi) x, y+1, z 1/2; (vii) x, y 1, z; (viii) x 1/2, y+3/2, z. sup-8