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Acta Crystallogr Sect E Struct Rep Online. 2009 January 1; 65(Pt 1): m56.
Published online 2008 December 13. doi:  10.1107/S1600536808041408
PMCID: PMC2967899

[Bis(3-phenyl­prop-2-enyl­idene)propane-1,3-diamine-κ2 N,N′]dibromidocobalt(II)

Abstract

In the crystal structure of the title compound, [CoBr2(C21H22N2)], the CoII atom is four-coordinated by two bromide anions and two N atoms from the bidentate Schiff base ligand in a distorted tetra­hedral geometry.

Related literature

For a related compound, see: Srivastava et al. (1990 [triangle]).

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Object name is e-65-00m56-scheme1.jpg

Experimental

Crystal data

  • [CoBr2(C21H22N2)]
  • M r = 521.16
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-00m56-efi1.jpg
  • a = 14.0306 (19) Å
  • b = 11.9962 (16) Å
  • c = 13.6738 (19) Å
  • β = 110.375 (2)°
  • V = 2157.5 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 4.51 mm−1
  • T = 100 (2) K
  • 0.32 × 0.12 × 0.10 mm

Data collection

  • Bruker APEXII area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.323, T max = 0.659
  • 9901 measured reflections
  • 3802 independent reflections
  • 3275 reflections with I > 2σ(I)
  • R int = 0.023

Refinement

  • R[F 2 > 2σ(F 2)] = 0.031
  • wR(F 2) = 0.080
  • S = 1.01
  • 3802 reflections
  • 235 parameters
  • H-atom parameters constrained
  • Δρmax = 0.96 e Å−3
  • Δρmin = −0.34 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808041408/hg2447sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808041408/hg2447Isup2.hkl

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

Acknowledgments

The authors thank Yasouj University for funding this study and the University of Malaya for buying the X-ray diffractometer.

supplementary crystallographic information

Comment

Synthesis of a new four-coordinated complex of Co(II) is to identify the steric arrangement with this type of bidentate ligand and could lead to either pseudo-tetrahedral or square planar geometry. Reaction of anhydrous CoBr2 with the ligand, N,N-bis(3-phenyl-propenylidene)-1,3-propanediamine has yielded the title compound with distorted tetrahedral geometry.

Experimental

The ligand of N,N-bis(3-phenyl-propenylidene)-1,3-propanediamine was prepared by condensation of 2?mmol of cinnamaldehyde and 1 mmol ethylenediamine in 10 ml dichloromethane. The mixture was cooled in an ice bath and then was added dropwise to a solution of 1 mmol anhydrous CoBr2 in 10 ml dichloromethane under nitrogen atmosphere. The mixture was stirred for 3 h and then filtered. To filtrate, 20 ml chloroform was added and kept overnight. The crystals suitable for X-ray were filtered off and washed with chloroform (64% yield). Elemental analysis for C21H22Br2CoN2 Calcd. C, 48.40; H, 4.25; N, 5.38%; Found: C, 48.32; H,4.21; N, 5.32%.

Refinement

All H atoms were placed at calculated positions (C—H O.95 - 0.99Å) with Uiso(H) set to 1.2 times Ueq(C).

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of the title complex at 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

[CoBr2(C21H22N2)]F(000) = 1036
Mr = 521.16Dx = 1.604 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4346 reflections
a = 14.0306 (19) Åθ = 2.3–29.6°
b = 11.9962 (16) ŵ = 4.51 mm1
c = 13.6738 (19) ÅT = 100 K
β = 110.375 (2)°Block, green
V = 2157.5 (5) Å30.32 × 0.12 × 0.10 mm
Z = 4

Data collection

Bruker APEXII area-detector diffractometer3802 independent reflections
Radiation source: fine-focus sealed tube3275 reflections with I > 2σ(I)
graphiteRint = 0.023
ω scanθmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −16→16
Tmin = 0.323, Tmax = 0.659k = −14→14
9901 measured reflectionsl = −15→16

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080H-atom parameters constrained
S = 1.01w = 1/[σ2(Fo2) + (0.045P)2 + 2.376P] where P = (Fo2 + 2Fc2)/3
3802 reflections(Δ/σ)max < 0.001
235 parametersΔρmax = 0.96 e Å3
0 restraintsΔρmin = −0.34 e Å3

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
Br10.43506 (3)0.59326 (3)0.13742 (3)0.02898 (11)
Br20.17275 (3)0.75199 (3)0.04140 (3)0.02782 (11)
Co0.28730 (4)0.63613 (4)−0.00789 (3)0.02382 (13)
N10.3244 (2)0.6980 (3)−0.1274 (2)0.0278 (7)
N20.2176 (2)0.4912 (2)−0.0717 (2)0.0286 (7)
C10.3361 (4)1.0847 (3)0.0581 (3)0.0456 (11)
H1A0.30941.01670.07320.055*
C20.3418 (4)1.1776 (4)0.1210 (4)0.0498 (11)
H2A0.31881.17250.17850.060*
C30.3802 (3)1.2761 (3)0.1007 (4)0.0433 (10)
H3A0.38461.33890.14440.052*
C40.4120 (3)1.2839 (3)0.0176 (3)0.0397 (10)
H4A0.43791.35270.00310.048*
C50.4070 (3)1.1931 (3)−0.0459 (3)0.0385 (10)
H5A0.42951.2000−0.10350.046*
C60.3690 (3)1.0907 (3)−0.0263 (3)0.0327 (9)
C70.3671 (3)0.9943 (3)−0.0910 (3)0.0354 (9)
H7A0.38321.0071−0.15210.042*
C80.3451 (3)0.8893 (3)−0.0736 (3)0.0304 (8)
H8A0.32830.8738−0.01340.037*
C90.3458 (3)0.7994 (3)−0.1420 (3)0.0311 (8)
H9A0.36310.8156−0.20170.037*
C100.3299 (3)0.6147 (3)−0.2044 (3)0.0329 (9)
H10A0.38950.5657−0.17250.039*
H10B0.33890.6531−0.26470.039*
C110.2336 (3)0.5444 (3)−0.2418 (3)0.0340 (9)
H11A0.17450.5939−0.25200.041*
H11B0.22670.5121−0.31060.041*
C120.2293 (3)0.4507 (3)−0.1697 (3)0.0375 (9)
H12A0.17140.4012−0.20660.045*
H12B0.29240.4061−0.15200.045*
C130.1673 (3)0.4295 (3)−0.0322 (3)0.0318 (8)
H13A0.13700.3643−0.06960.038*
C140.1526 (3)0.4507 (3)0.0653 (3)0.0297 (8)
H14A0.18310.51430.10550.036*
C150.0965 (3)0.3817 (3)0.0998 (3)0.0313 (8)
H15A0.06660.32010.05630.038*
C160.0764 (3)0.3912 (3)0.1974 (3)0.0293 (8)
C170.0274 (3)0.3040 (3)0.2283 (3)0.0322 (8)
H17A0.00610.24060.18440.039*
C180.0091 (3)0.3078 (3)0.3206 (3)0.0354 (9)
H18A−0.02380.24710.34020.043*
C190.0385 (3)0.3995 (3)0.3848 (3)0.0364 (9)
H19A0.02620.40210.44880.044*
C200.0866 (3)0.4888 (4)0.3552 (3)0.0373 (9)
H20A0.10710.55210.39930.045*
C210.1046 (3)0.4853 (3)0.2625 (3)0.0347 (9)
H21A0.13620.54690.24240.042*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.0299 (2)0.0322 (2)0.02463 (19)0.00440 (15)0.00925 (15)0.00136 (15)
Br20.0296 (2)0.02873 (19)0.0292 (2)0.00210 (15)0.01535 (15)−0.00126 (15)
Co0.0262 (3)0.0260 (3)0.0212 (2)0.0021 (2)0.0107 (2)0.00126 (19)
N10.0265 (16)0.0358 (18)0.0228 (15)0.0092 (14)0.0106 (13)0.0055 (13)
N20.0319 (16)0.0307 (16)0.0220 (15)0.0019 (14)0.0078 (13)0.0000 (13)
C10.060 (3)0.034 (2)0.050 (3)−0.014 (2)0.028 (2)0.004 (2)
C20.068 (3)0.037 (2)0.052 (3)−0.012 (2)0.030 (2)−0.001 (2)
C30.041 (2)0.032 (2)0.054 (3)−0.0029 (19)0.013 (2)0.005 (2)
C40.029 (2)0.027 (2)0.058 (3)−0.0019 (17)0.0083 (19)0.012 (2)
C50.027 (2)0.041 (2)0.048 (2)0.0038 (18)0.0133 (18)0.020 (2)
C60.0232 (19)0.033 (2)0.040 (2)−0.0012 (16)0.0086 (17)0.0112 (17)
C70.030 (2)0.041 (2)0.038 (2)0.0031 (18)0.0145 (17)0.0157 (18)
C80.0246 (18)0.038 (2)0.032 (2)0.0037 (16)0.0143 (16)0.0099 (17)
C90.0229 (18)0.043 (2)0.030 (2)0.0056 (17)0.0127 (16)0.0143 (18)
C100.034 (2)0.043 (2)0.0262 (19)0.0143 (18)0.0161 (17)0.0061 (17)
C110.042 (2)0.039 (2)0.0235 (19)0.0099 (19)0.0144 (17)−0.0010 (17)
C120.053 (3)0.035 (2)0.027 (2)0.0027 (19)0.0169 (19)−0.0055 (17)
C130.034 (2)0.0276 (19)0.031 (2)−0.0017 (17)0.0072 (17)−0.0023 (16)
C140.0291 (19)0.0301 (19)0.0258 (18)−0.0031 (16)0.0044 (15)0.0005 (16)
C150.028 (2)0.0303 (19)0.032 (2)−0.0077 (16)0.0060 (16)−0.0031 (16)
C160.0198 (18)0.033 (2)0.032 (2)−0.0022 (16)0.0039 (15)0.0016 (16)
C170.029 (2)0.028 (2)0.038 (2)−0.0001 (16)0.0100 (17)0.0014 (17)
C180.0249 (19)0.036 (2)0.046 (2)0.0023 (17)0.0140 (18)0.0096 (19)
C190.030 (2)0.047 (2)0.035 (2)0.0060 (19)0.0141 (17)0.0045 (19)
C200.032 (2)0.041 (2)0.040 (2)−0.0026 (18)0.0141 (18)−0.0102 (18)
C210.030 (2)0.035 (2)0.039 (2)−0.0036 (17)0.0121 (17)0.0011 (18)

Geometric parameters (Å, °)

Br1—Co2.3753 (6)C10—C111.523 (5)
Br2—Co2.3924 (6)C10—H10A0.9900
Co—N12.021 (3)C10—H10B0.9900
Co—N22.037 (3)C11—C121.510 (5)
N1—C91.286 (5)C11—H11A0.9900
N1—C101.474 (5)C11—H11B0.9900
N2—C131.266 (5)C12—H12A0.9900
N2—C121.487 (4)C12—H12B0.9900
C1—C61.386 (5)C13—C141.441 (5)
C1—C21.393 (6)C13—H13A0.9500
C1—H1A0.9500C14—C151.336 (5)
C2—C31.366 (6)C14—H14A0.9500
C2—H2A0.9500C15—C161.461 (5)
C3—C41.361 (6)C15—H15A0.9500
C3—H3A0.9500C16—C171.396 (5)
C4—C51.379 (6)C16—C211.406 (5)
C4—H4A0.9500C17—C181.373 (5)
C5—C61.402 (5)C17—H17A0.9500
C5—H5A0.9500C18—C191.379 (6)
C6—C71.451 (6)C18—H18A0.9500
C7—C81.338 (5)C19—C201.399 (6)
C7—H7A0.9500C19—H19A0.9500
C8—C91.429 (5)C20—C211.376 (5)
C8—H8A0.9500C20—H20A0.9500
C9—H9A0.9500C21—H21A0.9500
N1—Co—N2100.80 (12)N1—C10—H10B109.5
N1—Co—Br1111.12 (8)C11—C10—H10B109.5
N2—Co—Br1108.83 (9)H10A—C10—H10B108.1
N1—Co—Br2113.70 (8)C12—C11—C10115.2 (3)
N2—Co—Br2110.32 (8)C12—C11—H11A108.5
Br1—Co—Br2111.49 (2)C10—C11—H11A108.5
C9—N1—C10117.3 (3)C12—C11—H11B108.5
C9—N1—Co127.8 (3)C10—C11—H11B108.5
C10—N1—Co114.9 (2)H11A—C11—H11B107.5
C13—N2—C12116.6 (3)N2—C12—C11112.8 (3)
C13—N2—Co124.9 (2)N2—C12—H12A109.0
C12—N2—Co118.5 (2)C11—C12—H12A109.0
C6—C1—C2120.6 (4)N2—C12—H12B109.0
C6—C1—H1A119.7C11—C12—H12B109.0
C2—C1—H1A119.7H12A—C12—H12B107.8
C3—C2—C1120.6 (4)N2—C13—C14124.9 (3)
C3—C2—H2A119.7N2—C13—H13A117.5
C1—C2—H2A119.7C14—C13—H13A117.5
C4—C3—C2119.7 (4)C15—C14—C13120.6 (3)
C4—C3—H3A120.1C15—C14—H14A119.7
C2—C3—H3A120.1C13—C14—H14A119.7
C3—C4—C5120.7 (4)C14—C15—C16126.8 (3)
C3—C4—H4A119.6C14—C15—H15A116.6
C5—C4—H4A119.6C16—C15—H15A116.6
C4—C5—C6120.8 (4)C17—C16—C21118.0 (3)
C4—C5—H5A119.6C17—C16—C15119.3 (3)
C6—C5—H5A119.6C21—C16—C15122.7 (3)
C1—C6—C5117.6 (4)C18—C17—C16121.5 (4)
C1—C6—C7121.8 (3)C18—C17—H17A119.3
C5—C6—C7120.6 (3)C16—C17—H17A119.3
C8—C7—C6126.7 (3)C17—C18—C19120.2 (4)
C8—C7—H7A116.6C17—C18—H18A119.9
C6—C7—H7A116.6C19—C18—H18A119.9
C7—C8—C9122.6 (3)C18—C19—C20119.6 (4)
C7—C8—H8A118.7C18—C19—H19A120.2
C9—C8—H8A118.7C20—C19—H19A120.2
N1—C9—C8123.9 (3)C21—C20—C19120.3 (4)
N1—C9—H9A118.1C21—C20—H20A119.8
C8—C9—H9A118.1C19—C20—H20A119.8
N1—C10—C11110.7 (3)C20—C21—C16120.4 (4)
N1—C10—H10A109.5C20—C21—H21A119.8
C11—C10—H10A109.5C16—C21—H21A119.8
N2—Co—N1—C9160.1 (3)C10—N1—C9—C8−179.2 (3)
Br1—Co—N1—C9−84.6 (3)Co—N1—C9—C8−1.1 (5)
Br2—Co—N1—C942.1 (3)C7—C8—C9—N1−179.6 (4)
N2—Co—N1—C10−21.7 (3)C9—N1—C10—C11−130.3 (3)
Br1—Co—N1—C1093.5 (2)Co—N1—C10—C1151.3 (3)
Br2—Co—N1—C10−139.7 (2)N1—C10—C11—C12−80.7 (4)
N1—Co—N2—C13−169.1 (3)C13—N2—C12—C11147.5 (4)
Br1—Co—N2—C1374.0 (3)Co—N2—C12—C11−35.0 (4)
Br2—Co—N2—C13−48.7 (3)C10—C11—C12—N270.0 (4)
N1—Co—N2—C1213.6 (3)C12—N2—C13—C14176.2 (3)
Br1—Co—N2—C12−103.3 (3)Co—N2—C13—C14−1.1 (5)
Br2—Co—N2—C12134.1 (2)N2—C13—C14—C15178.7 (4)
C6—C1—C2—C3−0.2 (7)C13—C14—C15—C16178.8 (4)
C1—C2—C3—C40.8 (7)C14—C15—C16—C17−171.5 (4)
C2—C3—C4—C5−0.7 (6)C14—C15—C16—C218.5 (6)
C3—C4—C5—C60.0 (6)C21—C16—C17—C18−1.7 (5)
C2—C1—C6—C5−0.5 (6)C15—C16—C17—C18178.3 (3)
C2—C1—C6—C7177.9 (4)C16—C17—C18—C190.6 (6)
C4—C5—C6—C10.6 (6)C17—C18—C19—C200.2 (6)
C4—C5—C6—C7−177.8 (3)C18—C19—C20—C210.0 (6)
C1—C6—C7—C8−7.3 (6)C19—C20—C21—C16−1.2 (6)
C5—C6—C7—C8171.1 (4)C17—C16—C21—C201.9 (5)
C6—C7—C8—C9−179.6 (4)C15—C16—C21—C20−178.0 (4)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2447).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Srivastava, S., Srivastava, S. & Sharma, A. (1990). J. Indian Chem. Soc.67, 310–312.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2009). publCIF. In preparation.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography