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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 9| September 2010| Page m1122
https://doi.org/10.1107/S1600536810032174

Bis[2,4-di­bromo-6-(ethyl­imino­methyl)phenolato-κ2N,O]cobalt(II)

Chunyan Li,a* Rui Lia and Shufang Zhanga

aCollege of Health Science, Wuhan Institute of Physical Education, Wuhan 430079, People's Republic of China
*Correspondence e-mail: lichunyan2009@yahoo.com.cn

(Received 13 July 2010; accepted 10 August 2010; online 18 August 2010)

In the title compound, [Co(C9H8Br2NO)2], the CoII atom, located on a twofold axis, is in a pseudo-tetra­hedral environment, with two bidentate 2,4-dibromo-6-(ethyl­imino­meth­yl)phenolate Schiff base ligands acting as chelates through their phenolate O and azomethine N atoms. C—H⋯O hydrogen bonds link the complex mol­ecules to form a chain parallel to the b axis.

Related literature

For related Lewis base adducts, see: Akitsu et al. (2005[Akitsu, T., Takeuchi, Y. & Einaga, Y. (2005). Acta Cryst. E61, m772-m774.]); Bahron et al. (1994[Bahron, H., Larkworthy, L. F., Marecaux, A., Povey, D. C. & Smith, G. W. (1994). J. Chem. Crystallogr. 24, 145-147.]); Bermejo et al. (1996[Bermejo, M. R., Castineiras, A., Garcia-Monteagudo, J. C., Rey, M., Sousa, A., Watkinson, M., McAuliffe, C. A., Pritchard, R. G. & Beddoes, R. L. (1996). J. Chem. Soc. Dalton Trans. pp. 2935-2944.]); Elerman et al. (1996[Elerman, Y., Kabak, M. & Tahir, M. N. (1996). Acta Cryst. C52, 2434-2436.]); Groombridge et al. (1992[Groombridge, C. J., Larkworthy, L. F., Marecaux, A., Povey, D. C., Smith, G. W. & Mason, J. (1992). J. Chem. Soc. Dalton Trans. pp. 3125-3131.]); Li et al. (2008[Li, S., Wang, S.-B., Tang, K. & Ma, Y.-F. (2008). Acta Cryst. E64, m823.]); Maneiro et al. (2001[Maneiro, M., Bermejo, M. R., Fondo, M., Gonzalez, A. M., Sanmartin, J., Garcia-Monteagudo, J. C., Pritchard, R. G. & Tyryshkin, A. M. (2001). Polyhedron, 20, 711-719.]); Qiu et al. (2007[Qiu, X.-Y., Liu, W.-S. & Zhu, H.-L. (2007). Z. Anorg. Allg. Chem. 633, 1480-1484.]). For a related structure, see: Jiang et al. (2008[Jiang, W., Mo, G.-D. & Jin, L. (2008). Acta Cryst. E64, m1394.]). For standard bond-distance values, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data

  • [Co(C9H8Br2NO)2]

  • Mr = 670.90

  • Monoclinic, C 2/c

  • a = 22.116 (3) Å

  • b = 4.8645 (5) Å

  • c = 19.652 (2) Å

  • β = 100.038 (3)°

  • V = 2081.9 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 8.52 mm−1

  • T = 298 K

  • 0.30 × 0.21 × 0.11 mm
Data collection

  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.089, Tmax = 0.392

  • 6537 measured reflections

  • 2028 independent reflections

  • 1607 reflections with I > 2σ(I)

  • Rint = 0.099
Refinement

  • R[F2 > 2σ(F2)] = 0.060

  • wR(F2) = 0.161

  • S = 1.00

  • 2028 reflections

  • 124 parameters

  • H-atom parameters constrained

  • Δρmax = 1.39 e Å−3

  • Δρmin = −1.08 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C8—H8A⋯O1i 0.97 2.49 3.389 (8) 154
Symmetry code: (i) [-x+1, y-1, -z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEPIII (Burnett & Johnson, 1996[Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.]), ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).; software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810032174/dn2591sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810032174/dn2591Isup2.hkl

checkCIF report


Comment top

The Lewis base adducts of the 3,5-dibromosalicylidene group that are derived from the condensation of 3,5-dibromosalicylaldehyde and various primary amine are very interesting in a large number of transition metal complexes (Qiu et al., 2007; Akitsu et al., 2005; Maneiro et al., 2001; Bermejo et al., 1996). Recently, some mononuclear cobalt(II) compounds of Schiff base ligands derived from the condensation of salicylaldehyde with ethyl-, propyl- and butylamine have been structurally characterized (Li et al., 2008; Elerman et al., 1996; Bahron et al., 1994; Groombridge et al., 1992). As an extension of this work, the crystal structure of the title compound, (I), is reported here.

In (I), the Co atoms, located on a two fold axis, have pseudo-tetrahedral coordination environments with two bidentate Schiff base ligands,derived from the condensation of 3,5-dibromosalicylaldehyde and ethylamine, acting as chelates through their phenolate O and azomethine N atoms (Fig. 1). The structure is closely related to the Bis{2-[(E)-benzyliminomethyl]-4,6-dibromophenolato-κ2N, O}cobalt(II) compound (Jiang et al., 2008). The C7═N1 bond length of 1.287 (7) Å is similar to that of 1.288 (7) Å observed in the previously reported compound of Schiff base ligand, which was derived from the condensation of salicylaldehyde and isopropylamine (Elerman et al., 1996). The angle between the two O1—Co1—N1 planes of the molecule is equal to 82.80°. All bond lengths are within normal ranges (Allen et al., 1987).

In the crystal structure, the molecules are linked via intermolecular C—H···O hydrogen bonds forming a chain parallel to the b axis (Table 1, Fig. 2).

Related literature top

For related Lewis base adducts, see: Akitsu et al. (2005); Bahron et al. (1994); Bermejo et al. (1996); Elerman et al. (1996); Groombridge et al. (1992); Li et al. (2008); Maneiro et al. (2001); Qiu et al. (2007). For a related structure, see: Jiang et al. (2008). For standard bond-distance values, see: Allen et al. (1987).

Experimental top

3,5-Dibromosalicyladehyde (560 mg, 2 mmol) and ethylamine (90 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 66%). Analysis calculated for C18H16Br4CoN2O2: C 32.23, H 2.40, N 4.18%; found: C 32.11, H 2.55, N 4.00%. IR (KBr, cm-1): 3447, 2956, 2925, 2868, 2363, 1736, 1616, 1581, 1505, 1436, 1406, 1343, 1309, 1210, 1156, 1090, 1058, 974, 863, 840, 750, 708, 606, 534, 477.

Refinement top

All the H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H distances of 0.93–0.97 Å, and with Uiso(H) = 1.2Ueq(carrier) or 1.5Ueq(methyl groups).

Structure description top

The Lewis base adducts of the 3,5-dibromosalicylidene group that are derived from the condensation of 3,5-dibromosalicylaldehyde and various primary amine are very interesting in a large number of transition metal complexes (Qiu et al., 2007; Akitsu et al., 2005; Maneiro et al., 2001; Bermejo et al., 1996). Recently, some mononuclear cobalt(II) compounds of Schiff base ligands derived from the condensation of salicylaldehyde with ethyl-, propyl- and butylamine have been structurally characterized (Li et al., 2008; Elerman et al., 1996; Bahron et al., 1994; Groombridge et al., 1992). As an extension of this work, the crystal structure of the title compound, (I), is reported here.

In (I), the Co atoms, located on a two fold axis, have pseudo-tetrahedral coordination environments with two bidentate Schiff base ligands,derived from the condensation of 3,5-dibromosalicylaldehyde and ethylamine, acting as chelates through their phenolate O and azomethine N atoms (Fig. 1). The structure is closely related to the Bis{2-[(E)-benzyliminomethyl]-4,6-dibromophenolato-κ2N, O}cobalt(II) compound (Jiang et al., 2008). The C7═N1 bond length of 1.287 (7) Å is similar to that of 1.288 (7) Å observed in the previously reported compound of Schiff base ligand, which was derived from the condensation of salicylaldehyde and isopropylamine (Elerman et al., 1996). The angle between the two O1—Co1—N1 planes of the molecule is equal to 82.80°. All bond lengths are within normal ranges (Allen et al., 1987).

In the crystal structure, the molecules are linked via intermolecular C—H···O hydrogen bonds forming a chain parallel to the b axis (Table 1, Fig. 2).

For related Lewis base adducts, see: Akitsu et al. (2005); Bahron et al. (1994); Bermejo et al. (1996); Elerman et al. (1996); Groombridge et al. (1992); Li et al. (2008); Maneiro et al. (2001); Qiu et al. (2007). For a related structure, see: Jiang et al. (2008). For standard bond-distance values, see: Allen et al. (1987).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009).; software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The structure of the title compound (I), with the atom labeling scheme. Ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii. [Symmetry code: (i) 1 - x, y, 1/2 - z.]
[Figure 2] Fig. 2. Partial packing view showing the chain formed through C—H···O hydrogen bonds. H atoms not involved in hydrogen bondings have been omitted for clarity. H bonds are shown as dashed lines. [Symmetry code: (ii) -x + 1, y - 1, -z + 1/2.]
Bis[2,4-dibromo-6-(ethyliminomethyl)phenolato-κ2N,O]cobalt(II) top
Crystal data top
[Co(C9H8Br2NO)2]F(000) = 1284
Mr = 670.90Dx = 2.140 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 2472 reflections
a = 22.116 (3) Åθ = 2.6–27.2°
b = 4.8645 (5) ŵ = 8.52 mm−1
c = 19.652 (2) ÅT = 298 K
β = 100.038 (3)°Block, red
V = 2081.9 (4) Å30.30 × 0.21 × 0.11 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer		2028 independent reflections
Radiation source: fine-focus sealed tube1607 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.099
φ and ω scansθmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		h = −26→26
Tmin = 0.089, Tmax = 0.392k = −6→5
6537 measured reflectionsl = −24→22
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.161H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0865P)2]
where P = (Fo2 + 2Fc2)/3
2028 reflections(Δ/σ)max < 0.001
124 parametersΔρmax = 1.39 e Å−3
0 restraintsΔρmin = −1.08 e Å−3
Crystal data top
[Co(C9H8Br2NO)2]V = 2081.9 (4) Å3
Mr = 670.90Z = 4
Monoclinic, C2/cMo Kα radiation
a = 22.116 (3) ŵ = 8.52 mm−1
b = 4.8645 (5) ÅT = 298 K
c = 19.652 (2) Å0.30 × 0.21 × 0.11 mm
β = 100.038 (3)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		2028 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		1607 reflections with I > 2σ(I)
Tmin = 0.089, Tmax = 0.392Rint = 0.099
6537 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0600 restraints
wR(F2) = 0.161H-atom parameters constrained
S = 1.00Δρmax = 1.39 e Å−3
2028 reflectionsΔρmin = −1.08 e Å−3
124 parameters
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
Co10.50000.9495 (3)0.25000.0396 (3)
N10.44643 (19)0.7331 (11)0.3012 (2)0.0394 (11)
O10.43303 (17)1.1213 (9)0.1898 (2)0.0423 (10)
Br10.36561 (3)1.36837 (14)0.05745 (3)0.0477 (3)
Br20.18010 (3)0.63810 (17)0.10502 (4)0.0595 (3)
C10.3544 (2)0.8138 (12)0.2155 (3)0.0354 (12)
C20.3778 (2)1.0161 (13)0.1750 (3)0.0343 (12)
C30.3371 (3)1.1041 (12)0.1146 (3)0.0354 (13)
C40.2796 (2)0.9972 (13)0.0949 (3)0.0398 (13)
H40.25491.05680.05440.048*
C50.2587 (2)0.8016 (14)0.1352 (3)0.0405 (14)
C60.2942 (3)0.7099 (14)0.1949 (3)0.0438 (14)
H60.27890.57920.22190.053*
C70.3891 (3)0.6970 (13)0.2770 (3)0.0406 (13)
H70.36770.58200.30230.049*
C80.4728 (3)0.5890 (14)0.3657 (3)0.0508 (16)
H8A0.50980.49290.35930.061*
H8B0.44370.45380.37670.061*
C90.4878 (4)0.7869 (17)0.4243 (3)0.064 (2)
H9A0.51310.93190.41160.096*
H9B0.50940.69280.46420.096*
H9C0.45050.86340.43490.096*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Co10.0224 (5)0.0503 (8)0.0437 (6)0.000−0.0009 (4)0.000
N10.026 (2)0.043 (3)0.048 (3)0.006 (2)0.0011 (19)0.001 (2)
O10.0245 (19)0.047 (3)0.051 (2)−0.0072 (16)−0.0047 (17)0.0032 (19)
Br10.0393 (4)0.0488 (5)0.0511 (4)−0.0047 (2)−0.0036 (3)0.0089 (3)
Br20.0276 (4)0.0697 (6)0.0769 (5)−0.0128 (3)−0.0030 (3)−0.0035 (4)
C10.022 (2)0.040 (3)0.043 (3)0.002 (2)0.000 (2)−0.006 (2)
C20.026 (2)0.032 (3)0.042 (3)0.003 (2)−0.004 (2)−0.006 (2)
C30.029 (3)0.041 (4)0.035 (3)0.002 (2)0.003 (2)−0.002 (2)
C40.031 (3)0.043 (4)0.043 (3)0.003 (2)−0.003 (2)−0.005 (3)
C50.022 (2)0.051 (4)0.046 (3)0.000 (2)−0.001 (2)−0.008 (3)
C60.029 (3)0.044 (4)0.059 (4)−0.003 (3)0.010 (3)−0.002 (3)
C70.032 (3)0.041 (4)0.048 (3)−0.002 (2)0.007 (2)0.003 (3)
C80.039 (3)0.049 (4)0.058 (4)0.006 (3)−0.007 (3)0.010 (3)
C90.071 (5)0.077 (6)0.044 (4)0.016 (4)0.009 (3)0.009 (4)
Geometric parameters (Å, º) top
Co1—O1i1.918 (4)C3—C41.366 (8)
Co1—O11.918 (4)C4—C51.370 (9)
Co1—N1i1.985 (5)C4—H40.9300
Co1—N11.985 (5)C5—C61.367 (9)
N1—C71.287 (7)C6—H60.9300
N1—C81.477 (8)C7—H70.9300
O1—C21.310 (6)C8—C91.493 (10)
Br1—C31.886 (6)C8—H8A0.9700
Br2—C51.909 (5)C8—H8B0.9700
C1—C61.414 (8)C9—H9A0.9600
C1—C21.419 (8)C9—H9B0.9600
C1—C71.432 (8)C9—H9C0.9600
C2—C31.424 (8)
O1i—Co1—O1128.3 (3)C6—C5—C4121.4 (5)
O1i—Co1—N1i94.52 (17)C6—C5—Br2119.2 (5)
O1—Co1—N1i112.53 (19)C4—C5—Br2119.4 (4)
O1i—Co1—N1112.53 (19)C5—C6—C1120.0 (6)
O1—Co1—N194.52 (17)C5—C6—H6120.0
N1i—Co1—N1116.0 (3)C1—C6—H6120.0
C7—N1—C8118.0 (5)N1—C7—C1127.3 (6)
C7—N1—Co1121.5 (4)N1—C7—H7116.3
C8—N1—Co1120.4 (4)C1—C7—H7116.3
C2—O1—Co1123.9 (4)N1—C8—C9110.9 (6)
C6—C1—C2120.3 (5)N1—C8—H8A109.5
C6—C1—C7116.0 (6)C9—C8—H8A109.5
C2—C1—C7123.7 (5)N1—C8—H8B109.5
O1—C2—C1124.3 (5)C9—C8—H8B109.5
O1—C2—C3119.8 (5)H8A—C8—H8B108.0
C1—C2—C3115.9 (5)C8—C9—H9A109.5
C4—C3—C2122.9 (6)C8—C9—H9B109.5
C4—C3—Br1118.8 (4)H9A—C9—H9B109.5
C2—C3—Br1118.3 (4)C8—C9—H9C109.5
C3—C4—C5119.5 (5)H9A—C9—H9C109.5
C3—C4—H4120.2H9B—C9—H9C109.5
C5—C4—H4120.2
Symmetry code: (i) −x+1, y, −z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8A···O1ii0.972.493.389 (8)154
Symmetry code: (ii) −x+1, y−1, −z+1/2.

Experimental details

Crystal data
Chemical formula[Co(C9H8Br2NO)2]
Mr670.90
Crystal system, space groupMonoclinic, C2/c
Temperature (K)298
a, b, c (Å)22.116 (3), 4.8645 (5), 19.652 (2)
β (°) 100.038 (3)
V (Å3)2081.9 (4)
Z4
Radiation typeMo Kα
µ (mm−1)8.52
Crystal size (mm)0.30 × 0.21 × 0.11
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.089, 0.392
No. of measured, independent and
observed [I > 2σ(I)] reflections		6537, 2028, 1607
Rint0.099
(sin θ/λ)max (Å−1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.060, 0.161, 1.00
No. of reflections2028
No. of parameters124
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)1.39, −1.08

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)..

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8A···O1i0.972.493.389 (8)153.6
Symmetry code: (i) −x+1, y−1, −z+1/2.
 

Acknowledgements

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

References

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ISSN: 2056-9890
Volume 66| Part 9| September 2010| Page m1122
https://doi.org/10.1107/S1600536810032174
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