Bis[2,4-dibromo-6-(n-propyl­imino­methyl)phenolato-κ2 N,O]cobalt(II)

Chunyan Li; Rui Li; Shufang Zhang

doi:10.1107/S1600536810032162

. 2010 Aug 18;66(Pt 9):m1123. doi: 10.1107/S1600536810032162

Bis[2,4-dibromo-6-(n-propyliminomethyl)phenolato-κ² N,O]cobalt(II)

Chunyan Li ^a,^*, Rui Li ^a, Shufang Zhang ^a

PMCID: PMC3008039 PMID: 21588527

Abstract

In the title complex, [Co(C₁₀H₁₀Br₂NO)₂], the Co^II atom lies on a twofold rotation axis, the N₂O₂ units having distorted tetrahedral coordination environments comprising two bidentate chelate 2,4-dibromo-6-(n-propyliminomethyl)phenolate Schiff base ligands [Co—N = 1.989 (3) Å, Co—O = 1.924 (2) Å and O/N—Co—O/N = 94.53 (10)–125.40 (15)°]. In the crystal structure, the molecules are linked via weak intermolecular C—H⋯O hydrogen bonds [3.334 (5) Å] and there are also short inversion-related intermolecular Br⋯Br contacts [3.4263 (6) Å]

Related literature

For related compounds, see: Bermejo et al. (1996 ▶); Chen et al. (2007 ▶); Li & Wang (2007 ▶); Li et al. (2008 ▶); Maneiro et al. (2001 ▶); Qiu et al. (2007 ▶); Yuan et al. (2007 ▶). For standard bond-length values, see: Allen et al. (1987 ▶).

Experimental

Crystal data

[Co(C₁₀H₁₀Br₂NO)₂]
M _r = 698.91
Monoclinic,
a = 24.3684 (10) Å
b = 4.8555 (2) Å
c = 21.8132 (10) Å
β = 115.523 (4)°
V = 2329.08 (19) Å³
Z = 4
Mo Kα radiation
μ = 7.62 mm⁻¹
T = 296 K
0.32 × 0.22 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T _min = 0.097, T _max = 0.218
6076 measured reflections
2270 independent reflections
1657 reflections with I > 2σ(I)
R _int = 0.036

Refinement

R[F ² > 2σ(F ²)] = 0.030
wR(F ²) = 0.065
S = 1.00
2270 reflections
133 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.50 e Å⁻³

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXL97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL (Sheldrick, 2008 ▶); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810032162/zs2053sup1.cif

e-66-m1123-sup1.cif^{(14.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810032162/zs2053Isup2.hkl

e-66-m1123-Isup2.hkl^{(111.7KB, hkl)}

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

Acknowledgments

This work was supported by the Education Office of Hubei Province (grant No. D20104104).

supplementary crystallographic information

Comment

The Lewis base adducts of the 3,5-dibromosalicylidene compounds derived from the condensation of 3,5-dibromosalicylaldehyde with various primary amines are of interest, forming complexes with a large number of transition metals (Chen et al., 2007; Qiu et al., 2007; Maneiro et al., 2001; Bermejo et al., 1996). Recently, mononuclear zinc(II) and nickel(II) compounds of Schiff base ligands derived from the condensation of 3,5-dibromosalicylaldehyde with cyclopropylamine have been structurally characterized (Li & Wang, 2007; Yuan et al., 2007). As an extension of this work, the crystal structure of the title Co^II complex, [C₂₀H₂₀Br₄CoN₂O₂] (I), is reported here.

In (I), the Co^II atoms have distorted tetrahedral coordination environments with two bidentate Schiff base ligands, derived from the condensation of 3,5-dibromosalicylaldehyde and n-propylamine, acting as chelates through their phenolate O and azomethine N atoms [Co—N 1.989 (3) Å; Co—O 1.924 (2) Å; bond-angle range 94.53 (10)–125.40 (15)°] (Fig. 1). The Co atoms lie on two-fold rotation axes. The C7═N1 bond length of 1.274 (4) Å is somewhat shorter than 1.284 (2) Å observed in the previously reported compound of a Schiff base ligand derived from the condensation of salicylaldehyde with n-propylamine (Li et al., 2008). The angle between the two O1—Co1—N1 planes of the molecule is equal to 84.13°. All bond lengths are within normal ranges (Allen et al., 1987). In the crystal structure, the molecules are linked via weak intermolecular C—H···O hydrogen bonds and there are also short inversion-related inermolecular Br···Br contacts [3.4263 (6) Å] (Fig. 2).

Experimental

3,5-Dibromosalicylaldehyde (560 mg, 2 mmol) and n-propylamine (118 mg, 2 mmol) were dissolved in methanol (25 ml). The mixture was stirred for 30 min to give an orange solution, which was added to a methanol solution (15 ml) of Co(NO₃)₂.6H₂O (280 mg, 1 mmol). The mixture was stirred for another 20 min at room temperature to give a red solution and then filtered. The filtrate was kept in air for 5 d, forming red blocky crystals. The crystals were isolated, washed three times with distilled water and dried in a vacuum desiccator containing anhydrous CaCl₂ (yield 68%). Analysis calculated for C₂₀H₂₀Br₄CoN₂O₂: C 34.37, H 2.88, N 4.01%; found: C 34.17, H 2.90, N 3.99%. IR (KBr, cm^-1): 3447, 3062, 2966, 2877, 2359, 1619, 1577, 1504, 1434, 1407, 1307, 1212, 1161, 1095, 1040, 865, 838, 749, 705, 604, 466.