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Acta Cryst. (2008). E64, m113    [ doi:10.1107/S1600536807063908 ]

{2-Bromo-4-chloro-6-[2-(diethylamino)ethyliminomethyl]phenolato-[kappa]3N,N',O}(thiocyanato-[kappa]N)copper(II)

X.-W. Li and Y. Qiu

Abstract top

In the title compound, [Cu(C13H17BrClN2O)(NCS)], the Cu atom is in a slightly distorted square-planar geometry, coordinated by the three donor atoms of the ligand and the N atom of the isothiocyanate group.

Comment top

Schiff base compounds and metal complexes have been reported to have excellent biological activity (Shi et al., 2007; Panneerselvam et al., 2005, Singh et al., 2006, 2007; Zhong et al., 2006).

In the title compound the Cu atom is in a slightly distorted square planar geometry coordinated by the three donor atoms of the ligand and the N atom of the isothiocyanate group. (Fig. 1). The Cu atom is displaced out of the least-squares plane defined by the four donor atoms by 0.125 (2) Å. The coordination bond values (Table 1) are within normal ranges.

Related literature top

For the biological activity of Schiff base compounds, see: Panneerselvam et al. (2005); Shi et al. (2007); Singh et al. (2006, 2007); Zhong et al. (2006).

Experimental top

The title compound was obtained by the reaction of equimolar 3-bromo-5-chlorosalicylaldehyde, N,N-diethylethane-1,2-diamine, sodium thiocyanate, and copper acetate in an ethanol solution. Blue block-like single crystals were obtained by the slow evaporation of the filtrate in air.

Refinement top

H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93–0.97Å and with Uiso(H) = 1.2 (1.5 for methyl groups) times Ueq(C).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL (Sheldrick, 2001); molecular graphics: SHELXTL (Sheldrick, 2001); software used to prepare material for publication: SHELXTL (Sheldrick, 2001).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.
{2-Bromo-4-chloro-6-[2-(diethylamino)ethyliminomethyl]phenolato-\ κ3N,N',O}(thiocyanato-κN)copper(II) top
Crystal data top
[Cu(C13H17BrClN2O)(NCS)]F000 = 908
Mr = 454.27Dx = 1.744 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
a = 8.651 (2) ÅCell parameters from 3721 reflections
b = 14.137 (2) Åθ = 2.5–25.3º
c = 14.145 (2) ŵ = 3.85 mm−1
β = 90.820 (2)ºT = 293 (2) K
V = 1729.7 (5) Å3Block, blue
Z = 40.17 × 0.13 × 0.13 mm
Data collection top
Bruker SMART 1K CCD area-detector
diffractometer		3745 independent reflections
Radiation source: fine-focus sealed tube2784 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.039
T = 293(2) Kθmax = 27.0º
ω scansθmin = 2.0º
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)		h = −11→10
Tmin = 0.561, Tmax = 0.634k = −18→17
14228 measured reflectionsl = −18→18
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.123  w = 1/[σ2(Fo2) + (0.0599P)2 + 1.7229P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
3745 reflectionsΔρmax = 1.22 e Å−3
201 parametersΔρmin = −0.92 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Cu(C13H17BrClN2O)(NCS)]V = 1729.7 (5) Å3
Mr = 454.27Z = 4
Monoclinic, P21/cMo Kα
a = 8.651 (2) ŵ = 3.85 mm−1
b = 14.137 (2) ÅT = 293 (2) K
c = 14.145 (2) Å0.17 × 0.13 × 0.13 mm
β = 90.820 (2)º
Data collection top
Bruker SMART 1K CCD area-detector
diffractometer		3745 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)		2784 reflections with I > 2σ(I)
Tmin = 0.561, Tmax = 0.634Rint = 0.039
14228 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.045201 parameters
wR(F2) = 0.123H-atom parameters constrained
S = 1.04Δρmax = 1.22 e Å−3
3745 reflectionsΔρmin = −0.92 e Å−3
Special details top

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 F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 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 (Å2) top
xyzUiso*/Ueq
Cu10.13650 (6)0.16708 (3)0.07012 (3)0.03921 (16)
O1−0.0067 (4)0.2249 (2)−0.0153 (2)0.0503 (8)
N10.1195 (4)0.2692 (3)0.1611 (2)0.0424 (8)
N20.3230 (4)0.1260 (3)0.1541 (2)0.0436 (8)
N30.1631 (4)0.0684 (3)−0.0241 (3)0.0478 (9)
Br1−0.22122 (6)0.25006 (4)−0.17829 (3)0.05842 (18)
Cl1−0.33341 (16)0.58720 (9)0.00426 (11)0.0698 (4)
S10.10508 (13)−0.05745 (9)−0.17046 (8)0.0502 (3)
C1−0.0783 (5)0.3037 (3)−0.0054 (3)0.0410 (9)
C2−0.0611 (5)0.3662 (3)0.0729 (3)0.0422 (9)
C3−0.1405 (5)0.4526 (3)0.0746 (3)0.0518 (11)
H3−0.12690.49320.12580.062*
C4−0.2375 (5)0.4777 (3)0.0021 (3)0.0530 (11)
C5−0.2594 (5)0.4179 (4)−0.0741 (3)0.0520 (11)
H5−0.32590.4352−0.12340.062*
C6−0.1840 (5)0.3339 (3)−0.0770 (3)0.0423 (9)
C70.0380 (5)0.3446 (3)0.1520 (3)0.0481 (11)
H70.04370.38870.20070.058*
C80.2151 (6)0.2587 (4)0.2462 (3)0.0635 (15)
H8A0.29730.30530.24630.076*
H8B0.15280.26890.30180.076*
C90.2793 (9)0.1661 (4)0.2487 (4)0.087 (2)
H9A0.20510.12390.27740.104*
H9B0.37070.16710.28910.104*
C100.3261 (6)0.0234 (3)0.1647 (4)0.0616 (13)
H10A0.3399−0.00410.10260.074*
H10B0.22570.00340.18680.074*
C110.4495 (6)−0.0183 (4)0.2313 (4)0.0676 (15)
H11A0.54910.00640.21510.101*
H11B0.4503−0.08590.22510.101*
H11C0.4265−0.00150.29530.101*
C120.4629 (7)0.1734 (6)0.1237 (5)0.098 (2)
H12A0.45000.24050.13540.118*
H12B0.54720.15190.16420.118*
C130.5091 (7)0.1627 (7)0.0301 (5)0.117 (3)
H13A0.52280.09680.01640.175*
H13B0.60490.19550.02110.175*
H13C0.43140.1885−0.01160.175*
C140.1359 (4)0.0175 (3)−0.0848 (3)0.0380 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0451 (3)0.0384 (3)0.0339 (3)−0.0012 (2)−0.0085 (2)−0.0047 (2)
O10.069 (2)0.0402 (17)0.0409 (17)0.0084 (15)−0.0189 (14)−0.0043 (13)
N10.045 (2)0.051 (2)0.0313 (17)−0.0048 (17)−0.0055 (15)−0.0080 (15)
N20.044 (2)0.043 (2)0.0443 (19)−0.0070 (16)−0.0090 (15)0.0003 (15)
N30.051 (2)0.051 (2)0.0413 (19)0.0001 (17)−0.0050 (16)−0.0100 (17)
Br10.0689 (3)0.0642 (3)0.0418 (3)−0.0017 (2)−0.0130 (2)0.0037 (2)
Cl10.0715 (9)0.0532 (7)0.0852 (9)0.0218 (6)0.0219 (7)0.0123 (7)
S10.0508 (6)0.0547 (7)0.0451 (6)−0.0034 (5)−0.0002 (5)−0.0178 (5)
C10.043 (2)0.040 (2)0.040 (2)−0.0047 (18)0.0020 (17)0.0054 (18)
C20.042 (2)0.043 (2)0.042 (2)0.0003 (18)0.0053 (18)−0.0017 (18)
C30.058 (3)0.043 (3)0.055 (3)0.001 (2)0.012 (2)−0.003 (2)
C40.051 (3)0.048 (3)0.061 (3)0.011 (2)0.016 (2)0.010 (2)
C50.045 (3)0.059 (3)0.052 (3)0.006 (2)0.006 (2)0.016 (2)
C60.042 (2)0.047 (2)0.038 (2)−0.0041 (19)0.0026 (17)0.0073 (18)
C70.051 (3)0.050 (3)0.043 (2)−0.007 (2)0.0018 (19)−0.013 (2)
C80.055 (3)0.096 (4)0.039 (2)0.008 (3)−0.015 (2)−0.013 (2)
C90.134 (6)0.071 (4)0.055 (3)0.032 (4)−0.044 (3)−0.016 (3)
C100.054 (3)0.043 (3)0.087 (4)0.008 (2)−0.026 (3)−0.004 (2)
C110.062 (3)0.058 (3)0.082 (4)0.014 (3)−0.027 (3)0.001 (3)
C120.057 (4)0.145 (7)0.090 (5)−0.029 (4)−0.017 (3)0.032 (4)
C130.060 (4)0.196 (9)0.095 (5)−0.015 (5)0.020 (4)−0.066 (6)
C140.032 (2)0.040 (2)0.042 (2)0.0029 (17)−0.0011 (16)0.0012 (18)
Geometric parameters (Å, °) top
Cu1—O11.902 (3)C5—C61.356 (6)
Cu1—N11.940 (3)C5—H50.9300
Cu1—N31.945 (4)C7—H70.9300
Cu1—N22.073 (3)C8—C91.422 (7)
O1—C11.283 (5)C8—H8A0.9700
N1—C71.284 (6)C8—H8B0.9700
N1—C81.458 (5)C9—H9A0.9700
N2—C121.454 (7)C9—H9B0.9700
N2—C101.457 (6)C10—C111.532 (6)
N2—C91.507 (7)C10—H10A0.9700
N3—C141.143 (5)C10—H10B0.9700
Br1—C61.884 (4)C11—H11A0.9600
Cl1—C41.757 (5)C11—H11B0.9600
S1—C141.628 (4)C11—H11C0.9600
C1—C61.421 (6)C12—C131.397 (9)
C1—C21.421 (6)C12—H12A0.9700
C2—C31.402 (6)C12—H12B0.9700
C2—C71.433 (6)C13—H13A0.9600
C3—C41.363 (6)C13—H13B0.9600
C3—H30.9300C13—H13C0.9600
C4—C51.381 (7)
O1—Cu1—N192.66 (14)C9—C8—N1109.3 (4)
O1—Cu1—N387.45 (14)C9—C8—H8A109.8
N1—Cu1—N3176.83 (16)N1—C8—H8A109.8
O1—Cu1—N2168.15 (14)C9—C8—H8B109.8
N1—Cu1—N283.93 (14)N1—C8—H8B109.8
N3—Cu1—N295.33 (15)H8A—C8—H8B108.3
C1—O1—Cu1127.9 (3)C8—C9—N2115.3 (5)
C7—N1—C8118.1 (4)C8—C9—H9A108.4
C7—N1—Cu1126.7 (3)N2—C9—H9A108.4
C8—N1—Cu1115.1 (3)C8—C9—H9B108.4
C12—N2—C10118.3 (5)N2—C9—H9B108.4
C12—N2—C9108.0 (5)H9A—C9—H9B107.5
C10—N2—C9106.7 (4)N2—C10—C11117.3 (4)
C12—N2—Cu1110.2 (3)N2—C10—H10A108.0
C10—N2—Cu1110.5 (3)C11—C10—H10A108.0
C9—N2—Cu1101.5 (3)N2—C10—H10B108.0
C14—N3—Cu1160.4 (3)C11—C10—H10B108.0
O1—C1—C6119.3 (4)H10A—C10—H10B107.2
O1—C1—C2125.4 (4)C10—C11—H11A109.5
C6—C1—C2115.3 (4)C10—C11—H11B109.5
C3—C2—C1120.6 (4)H11A—C11—H11B109.5
C3—C2—C7117.4 (4)C10—C11—H11C109.5
C1—C2—C7122.0 (4)H11A—C11—H11C109.5
C4—C3—C2120.7 (4)H11B—C11—H11C109.5
C4—C3—H3119.7C13—C12—N2118.8 (6)
C2—C3—H3119.7C13—C12—H12A107.6
C3—C4—C5120.3 (4)N2—C12—H12A107.6
C3—C4—Cl1120.1 (4)C13—C12—H12B107.6
C5—C4—Cl1119.6 (4)N2—C12—H12B107.6
C6—C5—C4119.9 (4)H12A—C12—H12B107.1
C6—C5—H5120.0C12—C13—H13A109.5
C4—C5—H5120.0C12—C13—H13B109.5
C5—C6—C1123.1 (4)H13A—C13—H13B109.5
C5—C6—Br1119.8 (3)C12—C13—H13C109.5
C1—C6—Br1117.1 (3)H13A—C13—H13C109.5
N1—C7—C2125.2 (4)H13B—C13—H13C109.5
N1—C7—H7117.4N3—C14—S1177.3 (4)
C2—C7—H7117.4
Table 1
Selected geometric parameters (Å, °) top
Cu1—O11.902 (3)Cu1—N31.945 (4)
Cu1—N11.940 (3)Cu1—N22.073 (3)
O1—Cu1—N192.66 (14)O1—Cu1—N2168.15 (14)
O1—Cu1—N387.45 (14)N1—Cu1—N283.93 (14)
N1—Cu1—N3176.83 (16)N3—Cu1—N295.33 (15)
Acknowledgements top

The authors thank Minjiang University for financial support.

references
References top

Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Panneerselvam, P., Nair, R. R., Vijayalakshmi, G., Subramanian, E. H. & Krishnan, S. (2005). Eur. J. Med. Chem. 40, 225–229.

Sheldrick, G. M. (2001). SHELXTL. Version 5.0. Bruker AXS Inc., Madison, Wisconsin, USA.

Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.

Shi, L., Ge, H.-M., Tan, S.-H., Li, H.-Q., Song, Y.-C., Zhu, H.-L. & Tan, R.-X. (2007). Eur. J. Med. Chem. 42, 558–564.

Singh, K., Barwa, M. S. & Tyagi, P. (2006). Eur. J. Med. Chem. 41, 147–153.

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Zhong, X., Yi, J., Sun, J., Wei, H.-L., Liu, W.-S. & Yu, K.-B. (2006). Eur. J. Med. Chem. 41, 1090–1092.