metal-organic compounds
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1 metal-organic compounds Acta Crystallographica Section E Structure Reports Online ISSN [1,2-Bis(1H-benzimidazol-2-yl-jN 3 )- ethane]dichloridozinc(ii) Yan-Ling Zhou, a Ming-Hua Zeng a and Seik Weng Ng b * a School of Chemistry & Chemical Engineering, Guangxi Normal University, Guilin , People s Republic of China, and b Department of Chemistry, University of Malaya, Kuala Lumpur, Malaysia Correspondence seikweng@um.edu.my = 1.80 mm 1 T = 293 K Data collection Bruker SMART diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T min = 0.479, T max = Refinement R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections 415 parameters 1 restraint mm 8555 measured reflections 5820 independent reflections 4956 reflections with I > 2(I) R int = H-atom parameters constrained max = 0.30 e Å 3 min = 0.30 e Å 3 Absolute structure: Flack (1983), 2049 Friedel pairs Flack parameter: 0.1 (1) Received 8 December 2009; accepted 8 December 2009 Key indicators: single-crystal X-ray study; T = 293 K; mean (C C) = Å; R factor = 0.029; wr factor = 0.077; data-to-parameter ratio = The title compound, [ZnCl 2 (C 16 H 14 N 4 )], crystallizes with two molecules in the asymmetric unit. The Zn II atoms show distorted tetrahedral coordination environments. Adjacent molecules are linked by N HCl hydrogen bonds, forming a three-dimensional network. Related literature For the synthesis of the ligand, see: van Albada et al. (1995). For the zinc dichloride adduct of a similar N-heterocycle, see: Zhou et al. (2010). Table 1 Hydrogen-bond geometry (Å, ). D HA D H HA DA D HA N2 H2Cl (3) 137 N3 H3Cl4 i (3) 121 N6 H6Cl1 ii (3) 164 N7 H7Cl2 iii (3) 148 Symmetry codes: (i) x; y 1 2 ; z þ 2; (ii) x; y; z þ 1; (iii) x þ 1; y þ 1 2 ; z þ 2. Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X- SEED (Barbour, 2001); software used to prepare material for publication: publcif (Westrip, 2009). We thank Guangxi Normal University and the University of Malaya for supporting this study. Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5133). Experimental Crystal data [ZnCl 2 (C 16 H 14 N 4 )] M r = Monoclinic, P2 1 a = (4) Å b = (8) Å c = (8) Å = (1) V = (2) Å 3 Z =4 Mo K radiation References Albada, G. A. van, Lakin, M. T., Veldman, N., Spek, A. J. & Reedijk, J. (1995). Inorg. Chem. 34, Barbour, L. J. (2001). J. Supramol. Chem. 1, Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Flack, H. D. (1983). Acta Cryst. A39, Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Sheldrick, G. M. (2008). Acta Cryst. A64, Westrip, S. P. (2009). publcif. In preparation. Zhou, Y.-L., Zeng, M.-H. & Ng, S. W. (2010). Acta Cryst. E66, m58. Acta Cryst. (2010). E66, m57 doi: /s Zhou et al. m57
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3 Acta Cryst. (2010). E66, m57 [ doi: /s ] [1,2-Bis(1H-benzimidazol-2-yl- N 3 )ethane]dichloridozinc(ii) Y.-L. Zhou, M.-H. Zeng and S. W. Ng Experimental 1,4-Bis(2-benzimidazolyl)ethanebutane was synthesized by using a literature method (van Albada et al., 1995). To a solution of zinc chloride hexahydrate (0.25 g, 1 mmol) in ethanol (3 ml) was added an aqueous solution (4 ml) of the ligand (0.24 g, 1 mmol). The reactants were sealed in a 15-ml Teflon-lined, stainless-steel Parr bomb. The bomb was heated at 413 K for 3 days. The cool solution yielded single crystals in ca 30% yield. Refinement Hydrogen atoms were generated geometrically and were constrained to ride on their parent atoms [C H = Å; N H 0.88 Å U iso (H) = 1.2U eq (C, N)]. Figures Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of the two independent molecules of ZnCl 2 (C 16 H 14 N 4 ) at the 50% probability level; hydrogen atoms are drawn as sphere of arbitrary radius. [1,2-Bis(1H-benzimidazol-2-yl-κN 3 )ethane]dichloridozinc(ii) Crystal data [ZnCl 2 (C 16 H 14 N 4 )] F(000) = 808 M r = D x = Mg m 3 Monoclinic, P2 1 Mo Kα radiation, λ = Å Hall symbol: P 2yb Cell parameters from 4769 reflections a = (4) Å θ = b = (8) Å µ = 1.80 mm 1 c = (8) Å T = 293 K β = (1) Block, colorless V = (2) Å mm Z = 4 sup-1
4 Data collection Bruker SMART diffractometer Radiation source: fine-focus sealed tube graphite R int = independent reflections 4956 reflections with I > 2σ(I) φ and ω scans θ max = 27.1, θ min = 1.4 Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T min = 0.479, T max = h = k = measured reflections l = Refinement Refinement on F 2 Least-squares matrix: full R[F 2 > 2σ(F 2 )] = Secondary atom site location: difference Fourier map Hydrogen site location: inferred from neighbouring sites H-atom parameters constrained wr(f 2 ) = w = 1/[σ 2 (F o 2 ) + (0.0406P) 2 ] where P = (F o 2 + 2F c 2 )/3 S = 0.97 (Δ/σ) max = reflections Δρ max = 0.30 e Å parameters Δρ min = 0.30 e Å 3 1 restraint Absolute structure: Flack (1983), 2049 Friedel pairs Primary atom site location: structure-invariant direct methods Flack parameter: 0.1 (1) Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 ) x y z U iso */U eq Zn (5) (3) (2) (11) Zn (5) (3) (2) (11) Cl (11) (12) (6) (3) Cl (10) (9) (5) (2) Cl (13) (9) (6) (3) Cl (12) (9) (6) (3) N (4) (2) (19) (7) N (4) (3) (2) (8) H * N (4) (2) (2) (8) H * N (4) (2) (18) (7) N (4) (3) (18) (8) N (4) (3) (18) (7) H * N (4) (3) (2) (8) H * sup-2
5 N (4) (2) (19) (7) C (5) (3) (2) (9) C (5) (3) (3) (11) H2A * C (6) (4) (3) (13) H3A * C (6) (4) (4) (13) H * C (6) (4) (3) (12) H * C (5) (3) (3) (10) C (4) (3) (2) (8) C (5) (3) (2) (9) H8A * H8B * C (5) (3) (2) (10) H9A * H9B * C (4) (3) (2) (8) C (5) (3) (3) (9) C (5) (3) (3) (11) H * C (5) (3) (3) (12) H * C (5) (3) (3) (11) H * C (5) (3) (3) (10) H * C (4) (3) (2) (8) C (5) (3) (3) (9) C (6) (4) (3) (12) H * C (6) (4) (4) (14) H * C (6) (4) (3) (14) H * C (5) (4) (3) (12) H * C (5) (3) (3) (10) C (4) (3) (2) (8) C (4) (3) (2) (9) H24A * H24B * C (5) (3) (2) (9) H25A * H25B * C (4) (3) (2) (8) C (4) (3) (3) (9) C (5) (3) (3) (11) sup-3
6 H * C (5) (3) (3) (12) H * C (5) (4) (3) (12) H * C (5) (3) (3) (10) H * C (4) (3) (2) (9) Atomic displacement parameters (Å 2 ) U 11 U 22 U 33 U 12 U 13 U 23 Zn (2) (2) (18) (2) (14) (18) Zn (2) (3) (18) (2) (15) (18) Cl (5) (10) (5) (6) (4) (6) Cl (5) (6) (4) (5) (3) (5) Cl (6) (8) (5) (5) (4) (5) Cl (5) (8) (4) (5) (4) (5) N (18) (19) (15) (15) (13) (14) N (2) (2) (15) (18) (14) (15) N (2) (2) (17) (16) (14) (15) N (16) (19) (15) (14) (12) (13) N (18) (2) (15) (16) (13) (14) N (16) (2) (14) (18) (12) (16) N (16) (2) (17) (15) (13) (15) N (17) (2) (16) (14) (13) (14) C (2) (2) (19) (17) (16) (17) C (3) (3) (2) (2) (2) (2) C (3) (3) (3) (2) (2) (3) C (3) (3) (4) (2) (3) (3) C (3) (3) (3) (2) (2) (2) C (2) (2) (2) (19) (18) (18) C (2) (2) (18) (17) (15) (16) C (2) (2) (17) (2) (15) (2) C (3) (3) (18) (2) (16) (18) C (19) (2) (19) (17) (14) (17) C (2) (2) (2) (17) (16) (18) C (2) (3) (3) (2) (2) (2) C (2) (3) (3) (2) (2) (2) C (2) (3) (2) (2) (17) (2) C (2) (3) (2) (19) (17) (19) C (17) (2) (19) (16) (14) (17) C (2) (2) (2) (18) (16) (17) C (3) (3) (2) (3) (2) (2) C (3) (4) (3) (3) (3) (3) C (3) (3) (4) (2) (3) (3) C (3) (3) (3) (2) (2) (3) C (2) (3) (2) (19) (16) (2) sup-4
7 C (18) (2) (18) (17) (14) (16) C (19) (3) (16) (19) (14) (17) C (2) (3) (18) (18) (15) (18) C (18) (2) (2) (16) (15) (17) C (2) (3) (2) (17) (16) (19) C (2) (3) (3) (19) (2) (2) C (3) (3) (3) (2) (2) (3) C (2) (3) (3) (2) (2) (2) C (2) (3) (2) (2) (17) (19) C (19) (2) (2) (17) (16) (18) Geometric parameters (Å, ) Zn1 N (3) C8 H8B Zn1 N (3) C9 C (5) Zn1 Cl (1) C9 H9A Zn1 Cl (1) C9 H9B Zn2 N (3) C11 C (6) Zn2 N (3) C11 C (5) Zn2 Cl (1) C12 C (6) Zn2 Cl (1) C12 H N1 C (4) C13 C (6) N1 C (5) C13 H N2 C (5) C14 C (6) N2 C (5) C14 H N2 H C15 C (5) N3 C (5) C15 H N3 C (5) C17 C (6) N3 H C17 C (6) N4 C (4) C18 C (7) N4 C (5) C18 H N5 C (4) C19 C (7) N5 C (5) C19 H N6 C (5) C20 C (7) N6 C (5) C20 H N6 H C21 C (6) N7 C (5) C21 H N7 C (5) C23 C (6) N7 H C24 C (5) N8 C (4) C24 H24A N8 C (5) C24 H24B C1 C (5) C25 C (6) C1 C (5) C25 H25A C2 C (7) C25 H25B C2 H2A C27 C (6) C3 C (7) C27 C (5) C3 H3A C28 C (6) C4 C (7) C28 H C4 H C29 C (7) sup-5
8 C5 C (6) C29 H C5 H C30 C (6) C7 C (6) C30 H C8 C (6) C31 C (5) C8 H8A C31 H N1 Zn1 N (12) N3 C11 C (4) N1 Zn1 Cl (10) N3 C11 C (3) N4 Zn1 Cl (9) C12 C11 C (4) N1 Zn1 Cl (10) C13 C12 C (4) N4 Zn1 Cl (9) C13 C12 H Cl1 Zn1 Cl (3) C11 C12 H N8 Zn2 N (12) C12 C13 C (4) N8 Zn2 Cl (9) C12 C13 H N5 Zn2 Cl (10) C14 C13 H N8 Zn2 Cl (9) C15 C14 C (4) N5 Zn2 Cl (10) C15 C14 H Cl4 Zn2 Cl (4) C13 C14 H C7 N1 C (3) C14 C15 C (4) C7 N1 Zn (3) C14 C15 H C1 N1 Zn (2) C16 C15 H C7 N2 C (3) C11 C16 N (3) C7 N2 H C11 C16 C (4) C6 N2 H N4 C16 C (4) C10 N3 C (3) C18 C17 N (4) C10 N3 H C18 C17 C (4) C11 N3 H N5 C17 C (4) C10 N4 C (3) C19 C18 C (5) C10 N4 Zn (3) C19 C18 H C16 N4 Zn (2) C17 C18 H C23 N5 C (3) C18 C19 C (5) C23 N5 Zn (3) C18 C19 H C17 N5 Zn (3) C20 C19 H C23 N6 C (3) C21 C20 C (5) C23 N6 H C21 C20 H C22 N6 H C19 C20 H C26 N7 C (3) C20 C21 C (5) C26 N7 H C20 C21 H C27 N7 H C22 C21 H C26 N8 C (3) N6 C22 C (4) C26 N8 Zn (3) N6 C22 C (4) C32 N8 Zn (2) C21 C22 C (4) N1 C1 C (3) N5 C23 N (4) N1 C1 C (4) N5 C23 C (4) C6 C1 C (4) N6 C23 C (3) C3 C2 C (4) C23 C24 C (3) C3 C2 H2A C23 C24 H24A C1 C2 H2A C25 C24 H24A C2 C3 C (4) C23 C24 H24B C2 C3 H3A C25 C24 H24B sup-6
9 C4 C3 H3A H24A C24 H24B C5 C4 C (5) C26 C25 C (3) C5 C4 H C26 C25 H25A C3 C4 H C24 C25 H25A C4 C5 C (4) C26 C25 H25B C4 C5 H C24 C25 H25B C6 C5 H H25A C25 H25B N2 C6 C (4) N8 C26 N (4) N2 C6 C (4) N8 C26 C (4) C5 C6 C (4) N7 C26 C (3) N2 C7 N (4) C28 C27 N (4) N2 C7 C (3) C28 C27 C (4) N1 C7 C (3) N7 C27 C (4) C7 C8 C (3) C29 C28 C (4) C7 C8 H8A C29 C28 H C9 C8 H8A C27 C28 H C7 C8 H8B C28 C29 C (4) C9 C8 H8B C28 C29 H H8A C8 H8B C30 C29 H C10 C9 C (3) C31 C30 C (4) C10 C9 H9A C31 C30 H C8 C9 H9A C29 C30 H C10 C9 H9B C30 C31 C (4) C8 C9 H9B C30 C31 H H9A C9 H9B C32 C31 H N4 C10 N (3) N8 C32 C (3) N4 C10 C (4) N8 C32 C (4) N3 C10 C (3) C27 C32 C (4) N4 Zn1 N1 C (3) C12 C13 C14 C (6) Cl1 Zn1 N1 C (3) C13 C14 C15 C (6) Cl2 Zn1 N1 C (3) N3 C11 C16 N4 0.3 (4) N4 Zn1 N1 C (3) C12 C11 C16 N (4) Cl1 Zn1 N1 C (3) N3 C11 C16 C (3) Cl2 Zn1 N1 C (3) C12 C11 C16 C (6) N1 Zn1 N4 C (3) C10 N4 C16 C (4) Cl1 Zn1 N4 C (3) Zn1 N4 C16 C (2) Cl2 Zn1 N4 C (3) C10 N4 C16 C (4) N1 Zn1 N4 C (3) Zn1 N4 C16 C (5) Cl1 Zn1 N4 C (3) C14 C15 C16 C (5) Cl2 Zn1 N4 C (3) C14 C15 C16 N (3) N8 Zn2 N5 C (4) C23 N5 C17 C (4) Cl4 Zn2 N5 C (3) Zn2 N5 C17 C (6) Cl3 Zn2 N5 C (3) C23 N5 C17 C (4) N8 Zn2 N5 C (3) Zn2 N5 C17 C (2) Cl4 Zn2 N5 C (3) N5 C17 C18 C (5) Cl3 Zn2 N5 C (3) C22 C17 C18 C (7) N5 Zn2 N8 C (3) C17 C18 C19 C (8) Cl4 Zn2 N8 C (3) C18 C19 C20 C (8) Cl3 Zn2 N8 C (3) C19 C20 C21 C (7) sup-7
10 N5 Zn2 N8 C (3) C23 N6 C22 C (4) Cl4 Zn2 N8 C (3) C23 N6 C22 C (4) Cl3 Zn2 N8 C (3) C20 C21 C22 N (4) C7 N1 C1 C6 0.6 (4) C20 C21 C22 C (6) Zn1 N1 C1 C (3) C18 C17 C22 N (4) C7 N1 C1 C (4) N5 C17 C22 N6 0.1 (4) Zn1 N1 C1 C2 7.3 (6) C18 C17 C22 C (6) N1 C1 C2 C (4) N5 C17 C22 C (4) C6 C1 C2 C3 1.2 (6) C17 N5 C23 N6 0.8 (4) C1 C2 C3 C4 1.3 (7) Zn2 N5 C23 N (3) C2 C3 C4 C5 1.0 (8) C17 N5 C23 C (4) C3 C4 C5 C6 0.5 (7) Zn2 N5 C23 C (5) C7 N2 C6 C (5) C22 N6 C23 N5 0.7 (4) C7 N2 C6 C1 0.5 (4) C22 N6 C23 C (3) C4 C5 C6 N (5) N5 C23 C24 C (5) C4 C5 C6 C1 0.4 (7) N6 C23 C24 C (4) N1 C1 C6 N2 0.7 (4) C23 C24 C25 C (4) C2 C1 C6 N (4) C32 N8 C26 N7 0.8 (4) N1 C1 C6 C (4) Zn2 N8 C26 N (2) C2 C1 C6 C5 0.8 (6) C32 N8 C26 C (3) C6 N2 C7 N1 0.2 (5) Zn2 N8 C26 C (5) C6 N2 C7 C (4) C27 N7 C26 N8 0.8 (4) C1 N1 C7 N2 0.2 (4) C27 N7 C26 C (3) Zn1 N1 C7 N (2) C24 C25 C26 N (5) C1 N1 C7 C (4) C24 C25 C26 N (4) Zn1 N1 C7 C8 6.2 (5) C26 N7 C27 C (4) N2 C7 C8 C (4) C26 N7 C27 C (4) N1 C7 C8 C (5) N7 C27 C28 C (4) C7 C8 C9 C (4) C32 C27 C28 C (6) C16 N4 C10 N3 0.3 (4) C27 C28 C29 C (6) Zn1 N4 C10 N (2) C28 C29 C30 C (7) C16 N4 C10 C (4) C29 C30 C31 C (6) Zn1 N4 C10 C9 2.2 (6) C26 N8 C32 C (4) C11 N3 C10 N4 0.2 (4) Zn2 N8 C32 C (2) C11 N3 C10 C (3) C26 N8 C32 C (4) C8 C9 C10 N (6) Zn2 N8 C32 C (6) C8 C9 C10 N (4) C28 C27 C32 N (4) C10 N3 C11 C (4) N7 C27 C32 N8 0.0 (4) C10 N3 C11 C (4) C28 C27 C32 C (6) N3 C11 C12 C (4) N7 C27 C32 C (3) C16 C11 C12 C (6) C30 C31 C32 N (4) C11 C12 C13 C (6) C30 C31 C32 C (6) Hydrogen-bond geometry (Å, ) D H A D H H A D A D H A N2 H2 Cl (3) 137 N3 H3 Cl4 i (3) 121 N6 H6 Cl1 ii (3) 164 sup-8
11 N7 H7 Cl2 iii (3) 148 Symmetry codes: (i) x, y 1/2, z+2; (ii) x, y, z+1; (iii) x+1, y+1/2, z+2. Fig. 1 sup-9
Triclinic, P1 a = (2) Å b = (3) Å c = (4) Å = (1) = (1) = (1) Data collection.
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