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[Bis(3-phenyl­prop-2-enyl­­idene)propane-1,3-di­amine-κ2N,N′]di­bromidocobalt(II)

aDepartment of Chemistry, Yasouj University, Yasouj, 75918-74831, Iran, bCatalysis Division, Department of Chemistry, University of Isfahan, Isfahan, 81745-73441, Iran, cDepartment of Chemistry, Isfahan University of Technology, Isfahan, 84156-83111, Iran, and dDepartment of Chemistry, Faculty of Science, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: hapipah@um.edu.my

(Received 18 November 2008; accepted 7 December 2008; online 13 December 2008)

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[Srivastava, S., Srivastava, S. & Sharma, A. (1990). J. Indian Chem. Soc. 67, 310-312.]).

[Scheme 1]

Experimental

Crystal data
  • [CoBr2(C21H22N2)]

  • Mr = 521.16

  • Monoclinic, P 21 /c

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.323, Tmax = 0.659

  • 9901 measured reflections

  • 3802 independent reflections

  • 3275 reflections with I > 2σ(I)

  • Rint = 0.023

Refinement
  • R[F2 > 2σ(F2)] = 0.031

  • wR(F2) = 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[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 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: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supporting information


Comment top

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.

Related literature top

For a related compound, see: Sarivastava et al. (1990).

Experimental top

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 top

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

Computing details top

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

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of the title complex at 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
[Bis(3-phenylprop-2-enylidene)propane-1,3-diamine- κ2N,N']dibromidocobalt(II) top
Crystal data top
[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 top
Bruker APEXII area-detector
diffractometer
3802 independent reflections
Radiation source: fine-focus sealed tube3275 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
ω scanθmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1616
Tmin = 0.323, Tmax = 0.659k = 1414
9901 measured reflectionsl = 1516
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)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080H-atom parameters constrained
S = 1.01 w = 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
Crystal data top
[CoBr2(C21H22N2)]V = 2157.5 (5) Å3
Mr = 521.16Z = 4
Monoclinic, P21/cMo Kα radiation
a = 14.0306 (19) ŵ = 4.51 mm1
b = 11.9962 (16) ÅT = 100 K
c = 13.6738 (19) Å0.32 × 0.12 × 0.10 mm
β = 110.375 (2)°
Data collection top
Bruker APEXII area-detector
diffractometer
3802 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
3275 reflections with I > 2σ(I)
Tmin = 0.323, Tmax = 0.659Rint = 0.023
9901 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0310 restraints
wR(F2) = 0.080H-atom parameters constrained
S = 1.01Δρmax = 0.96 e Å3
3802 reflectionsΔρmin = 0.34 e Å3
235 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
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)
H5A0.42951.20000.10350.046*
C60.3690 (3)1.0907 (3)0.0263 (3)0.0327 (9)
C70.3671 (3)0.9943 (3)0.0910 (3)0.0354 (9)
H7A0.38321.00710.15210.042*
C80.3451 (3)0.8893 (3)0.0736 (3)0.0304 (8)
H8A0.32830.87380.01340.037*
C90.3458 (3)0.7994 (3)0.1420 (3)0.0311 (8)
H9A0.36310.81560.20170.037*
C100.3299 (3)0.6147 (3)0.2044 (3)0.0329 (9)
H10A0.38950.56570.17250.039*
H10B0.33890.65310.26470.039*
C110.2336 (3)0.5444 (3)0.2418 (3)0.0340 (9)
H11A0.17450.59390.25200.041*
H11B0.22670.51210.31060.041*
C120.2293 (3)0.4507 (3)0.1697 (3)0.0375 (9)
H12A0.17140.40120.20660.045*
H12B0.29240.40610.15200.045*
C130.1673 (3)0.4295 (3)0.0322 (3)0.0318 (8)
H13A0.13700.36430.06960.038*
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)
H18A0.02380.24710.34020.043*
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) top
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, º) top
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—C8179.2 (3)
Br1—Co—N1—C984.6 (3)Co—N1—C9—C81.1 (5)
Br2—Co—N1—C942.1 (3)C7—C8—C9—N1179.6 (4)
N2—Co—N1—C1021.7 (3)C9—N1—C10—C11130.3 (3)
Br1—Co—N1—C1093.5 (2)Co—N1—C10—C1151.3 (3)
Br2—Co—N1—C10139.7 (2)N1—C10—C11—C1280.7 (4)
N1—Co—N2—C13169.1 (3)C13—N2—C12—C11147.5 (4)
Br1—Co—N2—C1374.0 (3)Co—N2—C12—C1135.0 (4)
Br2—Co—N2—C1348.7 (3)C10—C11—C12—N270.0 (4)
N1—Co—N2—C1213.6 (3)C12—N2—C13—C14176.2 (3)
Br1—Co—N2—C12103.3 (3)Co—N2—C13—C141.1 (5)
Br2—Co—N2—C12134.1 (2)N2—C13—C14—C15178.7 (4)
C6—C1—C2—C30.2 (7)C13—C14—C15—C16178.8 (4)
C1—C2—C3—C40.8 (7)C14—C15—C16—C17171.5 (4)
C2—C3—C4—C50.7 (6)C14—C15—C16—C218.5 (6)
C3—C4—C5—C60.0 (6)C21—C16—C17—C181.7 (5)
C2—C1—C6—C50.5 (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—C7177.8 (3)C18—C19—C20—C210.0 (6)
C1—C6—C7—C87.3 (6)C19—C20—C21—C161.2 (6)
C5—C6—C7—C8171.1 (4)C17—C16—C21—C201.9 (5)
C6—C7—C8—C9179.6 (4)C15—C16—C21—C20178.0 (4)

Experimental details

Crystal data
Chemical formula[CoBr2(C21H22N2)]
Mr521.16
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)14.0306 (19), 11.9962 (16), 13.6738 (19)
β (°) 110.375 (2)
V3)2157.5 (5)
Z4
Radiation typeMo Kα
µ (mm1)4.51
Crystal size (mm)0.32 × 0.12 × 0.10
Data collection
DiffractometerBruker APEXII area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.323, 0.659
No. of measured, independent and
observed [I > 2σ(I)] reflections
9901, 3802, 3275
Rint0.023
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.031, 0.080, 1.01
No. of reflections3802
No. of parameters235
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.96, 0.34

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

 

Acknowledgements

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

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationSrivastava, S., Srivastava, S. & Sharma, A. (1990). J. Indian Chem. Soc. 67, 310–312.  CAS Google Scholar
First citationSheldrick, G. M. (1996). 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
First citationWestrip, S. P. (2009). publCIF. In preparation.  Google Scholar

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