Crystal structure of bis­[2-(benzo­thia­zol-2-yl)phenolato-κ2 N,O]copper(II)

Namhun Kim; Sung Kwon Kang

doi:10.1107/S2056989015015303

. 2015 Aug 22;71(Pt 9):m173–m174. doi: 10.1107/S2056989015015303

Crystal structure of bis[2-(benzothiazol-2-yl)phenolato-κ² N,O]copper(II)

Namhun Kim ^a, Sung Kwon Kang ^a,^*

PMCID: PMC4555420 PMID: 26396872

Abstract

In the title complex, [Cu(C₁₃H₈NOS)₂], the Cu^II atom is coordinated by two N atoms and two O atoms from two bidentate benzothiazolphenolate ligands, forming a distorted tetrahedral geometry [dihedral angle between two N—Cu—O planes: 45.1 (2)°]. The dihedral angles between the benzothiazole ring systems and the phenol rings are 4.1 (4) and 5.8 (4)°, indicating an almost planar geometry. Weak intra- and intermolecular C—H⋯O hydrogen bonds are observed. In the crystal, weak π–π interactions between aromatic and thiazole rings [centroid–centroid distances = 3.626 (3) and 3.873 (3) Å] link the molecules into a two-dimensional supramolecular network along the bc plane.

Keywords: crystal structure, Cu(II) complex, benzothiazolphenol, hydrogen bonding, π–π interactions

Related literature

For background to benzothiazole complexes and their applications, see: López-Banet et al. (2014 ▸); Liu et al. (2011 ▸); Booysen et al. (2010 ▸); Henary & Fahrni (2002 ▸). For the structures and luminescent properties of metal complexes, see: Yu et al. (2003 ▸); Katkova et al. (2011 ▸); Balashova et al. (2013 ▸); Wang et al. (2002 ▸). graphic file with name e-71-0m173-scheme1.jpg

Experimental

Crystal data

[Cu(C₁₃H₈NOS)₂]
M _r = 516.07
Monoclinic,
a = 7.8177 (17) Å
b = 21.195 (5) Å
c = 12.495 (3) Å
β = 91.077 (2)°
V = 2070.1 (8) Å³
Z = 4
Mo Kα radiation
μ = 1.29 mm⁻¹
T = 296 K
0.08 × 0.06 × 0.05 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ▸) T _min = 0.902, T _max = 0.925
21140 measured reflections
3855 independent reflections
2045 reflections with I > 2σ(I)
R _int = 0.149

Refinement

R[F ² > 2σ(F ²)] = 0.086
wR(F ²) = 0.224
S = 1.08
3855 reflections
298 parameters
H-atom parameters constrained
Δρ_max = 0.98 e Å⁻³
Δρ_min = −1.21 e Å⁻³

Data collection: SMART (Bruker, 2002 ▸); cell refinement: SAINT (Bruker, 2002 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: publCIF (Westrip, 2010 ▸).

Supplementary Material

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S2056989015015303/bq2400sup1.cif

e-71-0m173-sup1.cif^{(764.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015015303/bq2400Isup2.hkl

e-71-0m173-Isup2.hkl^{(307.5KB, hkl)}

Click here for additional data file.^{(1.3MB, tif)}

. DOI: 10.1107/S2056989015015303/bq2400fig1.tif

Molecular structure of the title complex, showing the atom-numbering scheme and 30% probability ellipsoids.

Click here for additional data file.^{(1.3MB, tif)}

via . DOI: 10.1107/S2056989015015303/bq2400fig2.tif

Dimeric formation via C—H⋯O (black dashed lines) and π-π (red) interactions.

Click here for additional data file.^{(3.8MB, tif)}

. DOI: 10.1107/S2056989015015303/bq2400fig3.tif

Part of the crystal structure of the title complex, showing the 2-D network of molecules linked by intermolecular C—H⋯O hydrogen bonds (black dashed lines) and π-π interactions (red).

CCDC reference: 1419096

Additional supporting information: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (, ).

DHA	DH	HA	D A	DHA
C4H4O33	0.93	2.41	2.997(12)	121
C7H7O17ⁱ	0.93	2.59	3.305(13)	134
C20H20O17	0.93	2.42	3.000(13)	121
C23H23O33ⁱⁱ	0.93	2.61	3.303(13)	132

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

This work was supported by the research fund of Chungnam National University.

supplementary crystallographic information

S1. Experimental

S1.1. Synthesis and crystallization

To a solution of 2-(2-hydroxyphenyl)benzothiazole (0.227 g, 1.0 mmol) in EtOH (15 ml) was added a 1N NaOH solution slowly until pH = 8 at room temperature. After 6 h of stirring, a solution of Cu(NO₃)₂.3H₂O (0.121g, 0.50 mmol) in EtOH (15 ml) was added. After 24 h of stirring at room temperature, the product was isolated as a dark green powder by removing the solvent. Green single crystals of the title complex were obtained by slow evaporation of its concentrated solution in dichloromethane at room temperature.

S1.2. Refinement

All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93 Å, and with U_iso(H) = 1.2U_eq(C).

S2. Results and discussion