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Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): m113.
Published online 2007 December 6. doi:  10.1107/S1600536807063908
PMCID: PMC2915066

{2-Bromo-4-chloro-6-[2-(diethyl­amino)ethyl­imino­meth­yl]phenolato-κ3 N,N′,O}(thio­cyanato-κN)copper(II)

Abstract

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.

Related literature

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

An external file that holds a picture, illustration, etc.
Object name is e-64-0m113-scheme1.jpg

Experimental

Crystal data

  • [Cu(C13H17BrClN2O)(NCS)]
  • M r = 454.27
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m113-efi1.jpg
  • a = 8.651 (2) Å
  • b = 14.137 (2) Å
  • c = 14.145 (2) Å
  • β = 90.820 (2)°
  • V = 1729.7 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 3.85 mm−1
  • T = 293 (2) K
  • 0.17 × 0.13 × 0.13 mm

Data collection

  • Bruker SMART 1K CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004 [triangle]) T min = 0.561, T max = 0.634
  • 14228 measured reflections
  • 3745 independent reflections
  • 2784 reflections with I > 2σ(I)
  • R int = 0.039

Refinement

  • R[F 2 > 2σ(F 2)] = 0.045
  • wR(F 2) = 0.123
  • S = 1.04
  • 3745 reflections
  • 201 parameters
  • H-atom parameters constrained
  • Δρmax = 1.22 e Å−3
  • Δρmin = −0.92 e Å−3

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

Table 1
Selected geometric parameters (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807063908/sg2212sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807063908/sg2212Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors thank Minjiang University for financial support.

supplementary crystallographic information

Comment

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.

Experimental

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

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).

Figures

Fig. 1.
The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.

Crystal data

[Cu(C13H17BrClN2O)(NCS)]F000 = 908
Mr = 454.27Dx = 1.744 Mg m3
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 mm1
β = 90.820 (2)ºT = 293 (2) K
V = 1729.7 (5) Å3Block, blue
Z = 40.17 × 0.13 × 0.13 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer3745 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

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 Å3
201 parametersΔρmin = −0.92 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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 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)

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)

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, °)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SG2212).

References

  • 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. [PubMed]
  • 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. [PubMed]
  • Singh, K., Barwa, M. S. & Tyagi, P. (2006). Eur. J. Med. Chem.41, 147–153. [PubMed]
  • Singh, K., Barwa, M. S. & Tyagi, P. (2007). Eur. J. Med. Chem.42, 394–402. [PubMed]
  • Zhong, X., Yi, J., Sun, J., Wei, H.-L., Liu, W.-S. & Yu, K.-B. (2006). Eur. J. Med. Chem.41, 1090–1092. [PubMed]

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