Data collection. Refinement. R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections 275 parameters
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1 organic compounds Acta Crystallographica Section E Structure Reports Online ISSN (4-Carboxy-1,3-thiazol-2-yl)pyridinium 3-carboxy-4-hydroxybenzenesulfonate dihydrate Zhong-Xiang Du* and Jun-Xia Li Data collection Bruker APEXII CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T min = 0.867, T max = Refinement R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections 275 parameters 7016 measured reflections 3494 independent reflections 3095 reflections with I > 2(I) R int = restraints H-atom parameters constrained max = 0.31 e Å 3 min = 0.29 e Å 3 Department of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang, Henan , People s Republic of China Correspondence dzx6281@126.com Received 1 September 2008; accepted 25 September 2008 Key indicators: single-crystal X-ray study; T = 291 K; mean (C C) = Å; R factor = 0.032; wr factor = 0.092; data-to-parameter ratio = In the crystal structure of the title compound, C 9 H 7 N 2 O 2 S + - C 7 H 5 O 6 S 2H 2 O, an H atom from the 5-sulfosalicylic acid is transferred to the pyridyl N atom, forming a salt. The dihedral angle between the thiazole and pyridinium rings is (5). The crystal packing is determined by O HO and N HO hydrogen bonds involving water molecules. Related literature For related structures, see: Chen et al. (2007); Ellsworth et al. (2006); Su et al. (2004). Table 1 Hydrogen-bond geometry (Å, ). D HA D H HA DA D HA O1 H1O (2) 146 O3 H3O (17) 171 O8 H8O4 i (18) 171 O9 H1WO6 ii (2) 165 O9 H2WO5 iii (2) 172 O10 H3WO (19) 129 O10 H4WO7 iv (2) 128 N2 H2DO10 v (2) 162 Symmetry codes: (i) x þ 1; y; z; (ii) x; y þ 1; z; (iii) x; y þ 1; z þ 1; (iv) x; y þ 1; z þ 1; (v) x þ 1; y þ 2; z þ 1. Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2; 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. This work was supported by the National Natural Science Foundation of China (No ) and the Natural Science Foundation of Henan Province (No ). Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KP2193). Experimental Crystal data C 9 H 7 N 2 O 2 S + C 7 H 5 O 6 S 2H 2 O M r = Triclinic, P1 a = (14) Å b = (17) Å c = (17) Å = (2) = (2) = (2) V = (3) Å 3 Z =2 Mo K radiation = 0.34 mm 1 T = 291 (2) K mm References Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Chen, X. D., Wu, H. F., Zhao, X. H., Zhao, X. J. & Du, M. (2007). Cryst. Growth Des. 7, Ellsworth, J. M., Su, C. Y., Khaliq, Z., Hipp, R. E., Goforth, A. M., Smith, M. D. & Loye, H. C. (2006). J. Mol. Struct. 796, Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Sheldrick, G. M. (2008). Acta Cryst. A64, Su, C. Y., Smith, M. D., Goforth, A. M. & Loye, H. C. (2004). Inorg. Chem. 43, o2044 Du and Li doi: /s
2 [doi: /s ] 4-(4-Carboxy-1,3-thiazol-2-yl)pyridinium 3-carboxy-4-hydroxybenzenesulfonate dihydrate Zhong-Xiang Du and Jun-Xia Li S1. Comment 2-(4-Pyridyl)thiazole-4-carboxylic acid (HPTCA), which is an asymmetric, chelating ligand, has been studied in recent years. Five of its transition metal complexes (Chen et al., 2007; Ellsworth et al., 2006; Su et al., 2004) were reported. In this paper we describe its salt with 5-sulfosalicylic acid (H 3 SSA), (I). The crystal structure of the title molecule comprises 2-(4-pyridylomium)thiazole-4-carboxylic acid, a 5-sulfosalicylic acid anion and two water molecules (Fig.1). The H atom of the 5-sulfosalicylic acid is transferred to the pyridyl N-atom of 2-(4-pyridyl)thiazole-4-carboxylic acid, thus forming a salt. The dihedral angle between the thiazole and pyridinium rings is (5). The N H and O H groups are involved in intra- and intermolecular hydrogen bonds with water molecules generating the 3-dimensional hydrogen bond network (Table 1 and Fig. 2). S2. Experimental The ligand HPTCA (1 mmol, 0.21 g) and H 3 SSA.2H 2 O (1 mmol, 0.25 g) were dissolved in solvent mixture of water and methanol (20 ml, v/v 1:1). To this solution, Cu(CH 3 COO) 2.4H 2 O (1 mmol, 0.26 g) was added and the resulting mixture was stirred and refluxed at 353 K for 3 h, then cooled to room temperature. After filtration and evaporation in air for five days, colourless claviform-shaped crystals were obtained in a yield of 43%. Analysis, found (%): C, 41.75; H, 3.51; N, 6.02; S, C 16 H 16 N 2 O 10 S 2 requires (%): C,41.70; H,3.47; N,6.08; S, (The elemental analysis indicates that the copper(ii) is not coordinated by the ligands) (CCDC number ) S3. Refinement H Atoms bonded to C or N atoms were positioned geometrically with C H distance of 0.93Å and N H distance of 0.86 Å, and treated as riding atoms, with U iso (H)=1.2U eq (C or N). H atoms bonded to O atoms were located in a difference Fourier map and refined isotropically. sup-1
3 Figure 1 Molecular structure of (I), with displacement ellipsoids drawn at the 30% probability level. Figure 2 The crystal packing of (I), showing hydrogen bonds as dashed lines. For the sake of clarity, H atoms on C atoms have been omitted. 4-(4-Carboxy-1,3-thiazol-2-yl)pyridinium 3-carboxy-4-hydroxybenzenesulfonate dihydrate Crystal data C 9 H 7 N 2 O 2 S + C 7 H 5 O 6 S 2H 2 O M r = Triclinic, P1 Hall symbol: -P 1 a = (14) Å b = (17) Å c = (17) Å α = (2) sup-2
4 β = (2) γ = (2) V = (3) Å 3 Z = 2 F(000) = 476 D x = Mg m 3 Mo Kα radiation, λ = Å Data collection Bruker APEXII CCD area-detector diffractometer Radiation source: fine-focus sealed tube Graphite monochromator φ and ω scans Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T min = 0.867, T max = Refinement Refinement on F 2 Least-squares matrix: full R[F 2 > 2σ(F 2 )] = wr(f 2 ) = S = reflections 275 parameters 6 restraints Primary atom site location: structure-invariant direct methods Secondary atom site location: difference Fourier map Cell parameters from 4068 reflections θ = µ = 0.34 mm 1 T = 291 K Claviform, colourless mm 7016 measured reflections 3494 independent reflections 3095 reflections with I > 2σ(I) R int = θ max = 25.5, θ min = 2.4 h = k = l = Hydrogen site location: inferred from neighbouring sites H-atom parameters constrained w = 1/[σ 2 (F o2 ) + (0.0504P) P] where P = (F o 2 + 2F c2 )/3 (Δ/σ) max < Δρ max = 0.31 e Å 3 Δρ min = 0.29 e Å 3 Extinction correction: SHELXL97, Fc * =kfc[ xfc 2 λ 3 /sin(2θ)] -1/4 Extinction coefficient: (2) 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 S (5) (4) (4) (14) S (5) (5) (4) (15) O (18) (14) (12) (4) H * sup-3
5 O (16) (12) (12) (3) O (15) (11) (12) (3) H * O (18) (12) (12) (4) O (16) (14) (15) (4) O (19) (13) (14) (4) O (18) (14) (16) (4) O (18) (13) (13) (4) H * O (18) (13) (15) (4) H1W * H2W * O (19) (14) (18) (5) H3W * H4W * N (17) (13) (13) (3) N (2) (15) (16) (4) H2D * C (19) (15) (15) (4) C (2) (18) (17) (4) H * C (2) (19) (17) (4) H3A * C (2) (17) (15) (4) C (19) (15) (14) (3) C (19) (15) (15) (3) H * C (19) (16) (15) (4) C (2) (17) (16) (4) H8A * C (2) (19) (18) (5) H * C (3) (18) (19) (5) H * C (2) (18) (18) (4) H * C (2) (16) (15) (4) C (2) (16) (15) (4) C (2) (16) (15) (4) C (2) (18) (17) (4) H * C (2) (17) (17) (4) Atomic displacement parameters (Å 2 ) U 11 U 22 U 33 U 12 U 13 U 23 S (3) (2) (3) (17) (18) (17) S (3) (3) (3) (2) (19) (2) sup-4
6 O (9) (8) (7) (7) (6) (6) O (8) (7) (7) (6) (6) (6) O (7) (6) (7) (5) (6) (5) O (10) (7) (7) (6) (6) (5) O (8) (8) (10) (6) (7) (7) O (10) (7) (9) (7) (8) (6) O (9) (8) (11) (7) (8) (7) O (9) (7) (8) (7) (7) (6) O (9) (7) (10) (6) (7) (7) O (9) (8) (14) (7) (9) (8) N (8) (7) (7) (6) (6) (6) N (11) (8) (10) (7) (8) (7) C (9) (8) (8) (7) (7) (7) C (10) (9) (10) (8) (8) (8) C (10) (11) (9) (8) (7) (8) C (9) (9) (8) (7) (7) (7) C (8) (8) (8) (7) (6) (6) C (8) (8) (8) (6) (6) (6) C (8) (8) (8) (7) (7) (7) C (10) (9) (9) (8) (7) (7) C (12) (10) (11) (9) (9) (8) C (13) (10) (11) (9) (10) (8) C (11) (10) (10) (8) (8) (8) C (9) (9) (8) (7) (7) (7) C (9) (9) (8) (7) (7) (7) C (9) (9) (8) (7) (7) (7) C (10) (10) (10) (8) (8) (8) C (10) (9) (10) (8) (8) (7) Geometric parameters (Å, º) S1 O (14) C1 C (2) S1 O (14) C1 C (2) S1 O (14) C2 C (3) S1 C (17) C2 H S2 C (19) C3 C (3) S2 C (17) C3 H3A O1 C (2) C4 C (2) O1 H C5 C (2) O2 C (2) C5 C (2) O3 C (2) C6 H O3 H C8 C (3) O7 C (2) C8 C (2) O8 C (2) C8 H8A O8 H C9 H O9 H1W C10 C (3) O9 H2W C10 H O10 H3W C11 C (2) sup-5
7 O10 H4W C11 H N1 C (2) C12 C (2) N1 C (2) C14 C (2) N2 C (3) C14 C (2) N2 C (3) C15 H N2 H2D O6 S1 O (9) C1 C6 H O6 S1 O (9) C5 C6 H O5 S1 O (9) O2 C7 O (16) O6 S1 C (8) O2 C7 C (16) O5 S1 C (8) O3 C7 C (14) O4 S1 C (8) C9 C8 C (17) C15 S2 C (8) C9 C8 H8A C4 O1 H C12 C8 H8A C7 O3 H N2 C9 C (18) C16 O8 H N2 C9 H H1W O9 H2W C8 C9 H H3W O10 H4W N2 C10 C (17) C13 N1 C (14) N2 C10 H C10 N2 C (17) C11 C10 H C10 N2 H2D C10 C11 C (18) C9 N2 H2D C10 C11 H C6 C1 C (15) C12 C11 H C6 C1 S (12) C11 C12 C (16) C2 C1 S (13) C11 C12 C (16) C3 C2 C (16) C8 C12 C (15) C3 C2 H N1 C13 C (15) C1 C2 H N1 C13 S (13) C2 C3 C (16) C12 C13 S (12) C2 C3 H3A N1 C14 C (16) C4 C3 H3A N1 C14 C (14) O1 C4 C (15) C15 C14 C (16) O1 C4 C (16) C14 C15 S (13) C3 C4 C (16) C14 C15 H C4 C5 C (15) S2 C15 H C4 C5 C (15) O7 C16 O (17) C6 C5 C (15) O7 C16 C (16) C1 C6 C (15) O8 C16 C (15) O6 S1 C1 C (13) C12 C8 C9 N2 0.8 (3) O5 S1 C1 C (16) C9 N2 C10 C (3) O4 S1 C1 C (15) N2 C10 C11 C (3) O6 S1 C1 C (17) C10 C11 C12 C8 1.5 (3) O5 S1 C1 C (15) C10 C11 C12 C (17) O4 S1 C1 C (15) C9 C8 C12 C (3) C6 C1 C2 C3 1.1 (3) C9 C8 C12 C (16) S1 C1 C2 C (13) C14 N1 C13 C (15) sup-6
8 C1 C2 C3 C4 0.3 (3) C14 N1 C13 S (18) C2 C3 C4 O (16) C11 C12 C13 N (16) C2 C3 C4 C5 1.7 (3) C8 C12 C13 N1 4.8 (2) O1 C4 C5 C (15) C11 C12 C13 S2 5.7 (2) C3 C4 C5 C6 1.6 (2) C8 C12 C13 S (13) O1 C4 C5 C7 0.9 (3) C15 S2 C13 N (14) C3 C4 C5 C (15) C15 S2 C13 C (15) C2 C1 C6 C5 1.1 (2) C13 N1 C14 C (2) S1 C1 C6 C (12) C13 N1 C14 C (15) C4 C5 C6 C1 0.2 (2) N1 C14 C15 S2 0.0 (2) C7 C5 C6 C (14) C16 C14 C15 S (15) C4 C5 C7 O2 1.7 (2) C13 S2 C15 C (14) C6 C5 C7 O (15) N1 C14 C16 O7 8.5 (3) C4 C5 C7 O (15) C15 C14 C16 O (2) C6 C5 C7 O3 1.2 (2) N1 C14 C16 O (15) C10 N2 C9 C8 0.6 (3) C15 C14 C16 O8 9.7 (3) Hydrogen-bond geometry (Å, º) D H A D H H A D A D H A O1 H1 O (2) 146 O3 H3 O (17) 171 O8 H8 O4 i (18) 171 O9 H1W O6 ii (2) 165 O9 H2W O5 iii (2) 172 O10 H3W O (19) 129 O10 H4W O7 iv (2) 128 N2 H2D O10 v (2) 162 Symmetry codes: (i) x+1, y, z; (ii) x, y+1, z; (iii) x, y+1, z+1; (iv) x, y+1, z+1; (v) x+1, y+2, z+1. sup-7
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