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Bis{4-bromo-2-[(2-hy­dr­oxy­eth­yl)imino­meth­yl]phenolato-κ3O,N,O′}cadmium

aSchool of Biological and Chemical Engineering, Jiaxing University, Jiaxing Zhejiang 314001, People's Republic of China
*Correspondence e-mail: jxxyyuj@yahoo.cn

(Received 25 June 2011; accepted 30 June 2011; online 6 July 2011)

The centrosymmetric title compound, [Cd(C9H9BrNO2)2], was obtained by the reaction of 5-bromo­salicyl­aldehyde, 2-amino­ethanol and cadmium nitrate in ethanol. The Cd atom, located on an inversion centre, is hexa­coordinated by two Schiff base ligands in an octa­hedral coordination through the phenolate O atom, the imine N atom and the hy­droxy O atoms. In the crystal, mol­ecules are linked through inter­molecular O—H⋯O hydrogen bonds, forming chains along the b axis.

Related literature

For the structures and properties of Schiff base Cd complexes, see: Sarkar et al. (2011[Sarkar, B. N., Choubey, S., Bhar, K., Chattopadhyay, S., Mitra, P. & Ghosh, B. K. (2011). J. Mol. Struct. 994, 306-312.]); Das et al. (2010[Das, S., Satapathi, S., Roy, S., Bhar, K., Mitra, P. & Ghosh, B. K. (2010). J. Mol. Struct. 982, 113-120.]); Fang & Nie (2010[Fang, Z.-L. & Nie, Q.-X. (2010). J. Coord. Chem. 63, 2328-2336.]); Niu et al. (2010[Niu, C.-Y., Dang, Y.-L., Zheng, X.-F., Wan, X.-S. & Kou, C.-H. (2010). Synth. React. Inorg. Met. Org. Nano-Met. Chem. 40, 40-44.]); Keypour et al. (2009[Keypour, H., Rezaeivala, M., Valencia, L., Salehzadeh, S., Perez-Lourido, P. & Khavasi, H. R. (2009). Polyhedron, 28, 3533-3541.]).

[Scheme 1]

Experimental

Crystal data
  • [Cd(C9H9BrNO2)2]

  • Mr = 598.56

  • Monoclinic, P 2/n

  • a = 10.207 (4) Å

  • b = 5.3275 (19) Å

  • c = 18.656 (7) Å

  • β = 99.156 (4)°

  • V = 1001.5 (6) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 5.11 mm−1

  • T = 298 K

  • 0.23 × 0.20 × 0.20 mm

Data collection
  • Bruker SMART 1K CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004[Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.]) Tmin = 0.386, Tmax = 0.428

  • 7794 measured reflections

  • 2172 independent reflections

  • 1524 reflections with I > 2σ(I)

  • Rint = 0.039

Refinement
  • R[F2 > 2σ(F2)] = 0.055

  • wR(F2) = 0.126

  • S = 1.02

  • 2172 reflections

  • 126 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 1.41 e Å−3

  • Δρmin = −1.55 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O2—H2⋯O1i 0.85 (1) 1.75 (2) 2.599 (7) 173 (9)
Symmetry code: (i) [-x+{\script{1\over 2}}, y-1, -z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

Supporting information


Comment top

Schiff base cadmium(II) complexes have been received much attention due to their interesting structures and luminescent properties (Sarkar et al., 2011; Das et al., 2010; Fang & Nie, 2010; Niu et al., 2010; Keypour et al., 2009).

The molecule of the title complex, (I) (Fig. 1), is centrosymmetric, with the inversion center located at the Cd atom. The Cd atom is hexa-coordinated by two Schiff base ligands, forming an octahedral coordination. The Schiff base coordinates to the Co atom through the phenolate O atom, the imine N atom, and the hydroxy O atom. The bond lengths are within normal values. In the crystal, molecules are linked through intermolecular O—H···O hydrogen bonds (Table 1), to form chains along the b axis, Fig. 2.

Related literature top

For the structures and properties of Schiff base–cadmium(II) complexes, see: Sarkar et al. (2011); Das et al. (2010); Fang & Nie (2010); Niu et al. (2010); Keypour et al. (2009).

Experimental top

To a solution of 5-bromosalicylaldehyde (0.181 g, 1.0 mmol), 2-aminoethanol (0.061 g, 1.0 mmol) in 20 ml absolute ethanol was added slowly a solution of cadmium nitrate (0.154 g, 0.5 mmol) in ethanol. The mixture was stirred for 2 h at room temperature to give a colorless solution, which was filtered and the filtrate was left to stand at room temperature. Colorless block crystals suitable for X-ray diffraction were obtained by slow evaporation.

Refinement top

H2 atom bonded to O2 atom was located in a difference map and refined with distance restraint of O—H = 0.85 (1) Å. Other H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93–0.97 Å.

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, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and local programs.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms. Unlabelled atoms are at the symmetry position 1/2 - x, y, 1/2 - z.
[Figure 2] Fig. 2. The packing of (I), viewed down the c axis. Hydrogen bonds are drawn as dashed lines. H atoms not involved in hydrogen bonding have been omitted.
Bis{4-bromo-2-[(2-hydroxyethyl)iminomethyl]phenolato- κ3O,N,O'}cadmium top
Crystal data top
[Cd(C9H9BrNO2)2]F(000) = 580
Mr = 598.56Dx = 1.985 Mg m3
Monoclinic, P2/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yacCell parameters from 1609 reflections
a = 10.207 (4) Åθ = 2.5–24.4°
b = 5.3275 (19) ŵ = 5.11 mm1
c = 18.656 (7) ÅT = 298 K
β = 99.156 (4)°Block, colorless
V = 1001.5 (6) Å30.23 × 0.20 × 0.20 mm
Z = 2
Data collection top
Bruker SMART 1K CCD area-detector
diffractometer
2172 independent reflections
Radiation source: fine-focus sealed tube1524 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.039
ω scansθmax = 27.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
h = 1312
Tmin = 0.386, Tmax = 0.428k = 66
7794 measured reflectionsl = 2323
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)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.034P)2 + 5.8476P]
where P = (Fo2 + 2Fc2)/3
2172 reflections(Δ/σ)max < 0.001
126 parametersΔρmax = 1.41 e Å3
1 restraintΔρmin = 1.55 e Å3
Crystal data top
[Cd(C9H9BrNO2)2]V = 1001.5 (6) Å3
Mr = 598.56Z = 2
Monoclinic, P2/nMo Kα radiation
a = 10.207 (4) ŵ = 5.11 mm1
b = 5.3275 (19) ÅT = 298 K
c = 18.656 (7) Å0.23 × 0.20 × 0.20 mm
β = 99.156 (4)°
Data collection top
Bruker SMART 1K CCD area-detector
diffractometer
2172 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
1524 reflections with I > 2σ(I)
Tmin = 0.386, Tmax = 0.428Rint = 0.039
7794 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0551 restraint
wR(F2) = 0.126H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 1.41 e Å3
2172 reflectionsΔρmin = 1.55 e Å3
126 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
Cd10.25000.38621 (12)0.25000.0491 (2)
Br10.21431 (12)0.4350 (3)0.64964 (5)0.1157 (5)
N10.4104 (7)0.2594 (14)0.3415 (3)0.0705 (19)
O10.2194 (5)0.6681 (8)0.3344 (2)0.0577 (13)
O20.3921 (6)0.0979 (9)0.2021 (3)0.0676 (14)
C10.3083 (7)0.4314 (13)0.4410 (3)0.0529 (17)
C20.2245 (7)0.6144 (12)0.4037 (3)0.0476 (15)
C30.1433 (9)0.7475 (15)0.4453 (4)0.073 (2)
H30.08930.87510.42310.087*
C40.1407 (9)0.6964 (18)0.5174 (4)0.081 (3)
H40.08420.78490.54280.097*
C50.2219 (9)0.5144 (17)0.5511 (4)0.069 (2)
C60.3057 (8)0.3868 (16)0.5151 (4)0.067 (2)
H60.36250.26770.53970.080*
C70.4004 (8)0.2792 (17)0.4087 (4)0.073 (2)
H70.45970.18400.44070.088*
C80.5021 (11)0.066 (2)0.3211 (5)0.112 (4)
H8A0.58950.09130.34930.134*
H8B0.47120.09870.33290.134*
C90.5113 (10)0.075 (2)0.2490 (6)0.113 (4)
H9A0.55510.07720.23660.136*
H9B0.56760.21510.24090.136*
H20.358 (8)0.047 (7)0.194 (5)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cd10.0826 (6)0.0363 (3)0.0287 (3)0.0000.0101 (3)0.000
Br10.1431 (11)0.1725 (13)0.0387 (5)0.0486 (9)0.0363 (6)0.0257 (6)
N10.082 (5)0.092 (5)0.038 (3)0.029 (4)0.011 (3)0.004 (3)
O10.107 (4)0.038 (2)0.030 (2)0.007 (2)0.018 (2)0.0017 (18)
O20.084 (4)0.056 (3)0.064 (3)0.005 (3)0.016 (3)0.026 (3)
C10.067 (5)0.060 (4)0.032 (3)0.008 (3)0.008 (3)0.000 (3)
C20.074 (5)0.037 (3)0.033 (3)0.004 (3)0.013 (3)0.002 (3)
C30.114 (7)0.062 (5)0.044 (4)0.024 (5)0.021 (4)0.003 (4)
C40.111 (7)0.095 (6)0.042 (4)0.033 (6)0.030 (4)0.000 (4)
C50.089 (6)0.086 (5)0.032 (4)0.017 (5)0.014 (4)0.004 (4)
C60.083 (6)0.081 (5)0.036 (4)0.021 (5)0.006 (4)0.004 (4)
C70.088 (6)0.095 (6)0.037 (4)0.035 (5)0.011 (4)0.007 (4)
C80.112 (8)0.166 (11)0.059 (5)0.078 (8)0.020 (5)0.005 (6)
C90.084 (7)0.157 (11)0.094 (7)0.031 (7)0.002 (6)0.069 (7)
Geometric parameters (Å, º) top
Cd1—O12.233 (4)C1—C71.443 (10)
Cd1—O1i2.233 (4)C2—C31.413 (10)
Cd1—N12.272 (6)C3—C41.376 (10)
Cd1—N1i2.272 (6)C3—H30.9300
Cd1—O2i2.382 (5)C4—C51.363 (11)
Cd1—O22.382 (5)C4—H40.9300
Br1—C51.900 (7)C5—C61.352 (11)
N1—C71.278 (8)C6—H60.9300
N1—C81.482 (10)C7—H70.9300
O1—C21.318 (7)C8—C91.364 (13)
O2—C91.387 (11)C8—H8A0.9700
O2—H20.850 (10)C8—H8B0.9700
C1—C21.405 (9)C9—H9A0.9700
C1—C61.407 (9)C9—H9B0.9700
O1—Cd1—O1i95.5 (2)C4—C3—C2122.8 (7)
O1—Cd1—N180.5 (2)C4—C3—H3118.6
O1i—Cd1—N1124.4 (2)C2—C3—H3118.6
O1—Cd1—N1i124.4 (2)C5—C4—C3119.1 (7)
O1i—Cd1—N1i80.5 (2)C5—C4—H4120.4
N1—Cd1—N1i145.4 (4)C3—C4—H4120.4
O1—Cd1—O2i90.41 (19)C6—C5—C4121.0 (7)
O1i—Cd1—O2i149.32 (19)C6—C5—Br1119.7 (6)
N1—Cd1—O2i86.3 (2)C4—C5—Br1119.3 (6)
N1i—Cd1—O2i71.4 (2)C5—C6—C1121.1 (7)
O1—Cd1—O2149.32 (19)C5—C6—H6119.5
O1i—Cd1—O290.41 (19)C1—C6—H6119.5
N1—Cd1—O271.4 (2)N1—C7—C1127.9 (7)
N1i—Cd1—O286.3 (2)N1—C7—H7116.1
O2i—Cd1—O299.7 (3)C1—C7—H7116.1
C7—N1—C8117.5 (7)C9—C8—N1112.1 (8)
C7—N1—Cd1123.5 (5)C9—C8—H8A109.2
C8—N1—Cd1115.0 (5)N1—C8—H8A109.2
C2—O1—Cd1123.9 (4)C9—C8—H8B109.2
C9—O2—Cd1110.2 (5)N1—C8—H8B109.2
C9—O2—H2109 (6)H8A—C8—H8B107.9
Cd1—O2—H2113 (6)C8—C9—O2115.7 (9)
C2—C1—C6119.8 (6)C8—C9—H9A108.3
C2—C1—C7124.7 (6)O2—C9—H9A108.3
C6—C1—C7115.5 (6)C8—C9—H9B108.3
O1—C2—C1124.2 (6)O2—C9—H9B108.3
O1—C2—C3119.7 (6)H9A—C9—H9B107.4
C1—C2—C3116.2 (6)
Symmetry code: (i) x+1/2, y, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O1ii0.85 (1)1.75 (2)2.599 (7)173 (9)
Symmetry code: (ii) x+1/2, y1, z+1/2.

Experimental details

Crystal data
Chemical formula[Cd(C9H9BrNO2)2]
Mr598.56
Crystal system, space groupMonoclinic, P2/n
Temperature (K)298
a, b, c (Å)10.207 (4), 5.3275 (19), 18.656 (7)
β (°) 99.156 (4)
V3)1001.5 (6)
Z2
Radiation typeMo Kα
µ (mm1)5.11
Crystal size (mm)0.23 × 0.20 × 0.20
Data collection
DiffractometerBruker SMART 1K CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2004)
Tmin, Tmax0.386, 0.428
No. of measured, independent and
observed [I > 2σ(I)] reflections
7794, 2172, 1524
Rint0.039
(sin θ/λ)max1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.055, 0.126, 1.02
No. of reflections2172
No. of parameters126
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)1.41, 1.55

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXTL (Sheldrick, 2008) and local programs.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O1i0.850 (10)1.754 (17)2.599 (7)173 (9)
Symmetry code: (i) x+1/2, y1, z+1/2.
 

Acknowledgements

The School of Biological and Chemical Engineering at Jiaxing University is acknowledged for the provision of facilities to prepare and crystallize the compound. Dr Yu-Xi Sun of Qufu Normal University is acknowledged for the data collection.

References

First citationBruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationDas, S., Satapathi, S., Roy, S., Bhar, K., Mitra, P. & Ghosh, B. K. (2010). J. Mol. Struct. 982, 113–120.  Web of Science CSD CrossRef CAS Google Scholar
First citationFang, Z.-L. & Nie, Q.-X. (2010). J. Coord. Chem. 63, 2328–2336.  Web of Science CSD CrossRef CAS Google Scholar
First citationKeypour, H., Rezaeivala, M., Valencia, L., Salehzadeh, S., Perez-Lourido, P. & Khavasi, H. R. (2009). Polyhedron, 28, 3533–3541.  Web of Science CSD CrossRef CAS Google Scholar
First citationNiu, C.-Y., Dang, Y.-L., Zheng, X.-F., Wan, X.-S. & Kou, C.-H. (2010). Synth. React. Inorg. Met. Org. Nano-Met. Chem. 40, 40–44.  CAS Google Scholar
First citationSarkar, B. N., Choubey, S., Bhar, K., Chattopadhyay, S., Mitra, P. & Ghosh, B. K. (2011). J. Mol. Struct. 994, 306–312.  Web of Science CSD CrossRef CAS Google Scholar
First citationSheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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