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Acta Cryst. (2009). E65, m1090    [ doi:10.1107/S1600536809032061 ]

Bis{2-[3-(dimethylamino)propyliminomethyl]-4,6-dihydroselenophenolato}zinc(II)

J. Yang, J.-W. Yuan, R.-H. Zha and Q.-F. Zeng

Abstract top

In the title complex, [Zn(C12H17N2OSe2)2], the ZnII ion is six-coordinated by two N,N',O-tridentate Schiff base ligands, resulting in a slightly distorted trans-ZnO2N4 octahedral coordination for the metal ion.

Comment top

There has been much research interest in Schiff base metal complexes due to their molecular architectures and biological activities (Shi et al., 2008; Xu et al., 2009). In this work, we report here the crystal structure of the title compound, (I). In (I), all bond lengths are within normal ranges (Allen et al., 1987) (Fig. 1). The Zn(II) is six-coordinated by two O and four N atoms from the two Schiff base ligands, forming a slightly distorted octahedral coordination (Table 1, Fig. 1).

Related literature top

For background to Schiff bases as ligands, see: Shi et al. (2008); Xu et al. (2009). For reference structural data see: Allen et al. (1987);

Experimental top

A mixture of 3,5-dihydroseleno-2-hydroxybenzaldehyde (564 mg, 2 mmol), N,N-dimethylpropane-1,3-diamine (204 mg, 2 mmol) and ZnCl2 (1 mmol, 134 mg) in methanol (10 ml) was stirred for 1 h. After keeping the filtrate in air for 7 d, colourless blocks of (I) were formed.

Refinement top

All H atoms were positioned geometrically (C—H = 0.93–0.96Å, Se—H = 0.82Å) and refined as riding, with Uiso(H) = 1.2Ueq(carrier) or 1.5Ueq(methyl C).

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing 30% probability displacement ellipsoids.
Bis{2-[3-(dimethylamino)propyliminomethyl]-4,6-dihydroselenophenolato}zinc(II) top
Crystal data top
[Zn(C12H17N2OSe2)2]F(000) = 3104
Mr = 791.76Dx = 1.852 Mg m−3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 25 reflections
a = 15.8066 (16) Åθ = 9–12°
b = 16.875 (3) ŵ = 6.02 mm−1
c = 21.297 (3) ÅT = 296 K
V = 5680.4 (13) Å3Block, colourless
Z = 80.35 × 0.28 × 0.24 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer		3434 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.064
graphiteθmax = 25.0°, θmin = 1.9°
ω/2θ scansh = −17→18
Absorption correction: ψ scan
(North et al., 1968)		k = −19→20
Tmin = 0.227, Tmax = 0.326l = −23→25
28494 measured reflections3 standard reflections every 200 reflections
5005 independent reflections intensity decay: 1%
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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0534P)2 + 15.0374P]
where P = (Fo2 + 2Fc2)/3
5005 reflections(Δ/σ)max = 0.001
324 parametersΔρmax = 0.66 e Å−3
0 restraintsΔρmin = −1.41 e Å−3
Crystal data top
[Zn(C12H17N2OSe2)2]V = 5680.4 (13) Å3
Mr = 791.76Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 15.8066 (16) ŵ = 6.02 mm−1
b = 16.875 (3) ÅT = 296 K
c = 21.297 (3) Å0.35 × 0.28 × 0.24 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer		3434 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)		Rint = 0.064
Tmin = 0.227, Tmax = 0.326θmax = 25.0°
28494 measured reflections3 standard reflections every 200 reflections
5005 independent reflections intensity decay: 1%
Refinement top
R[F2 > 2σ(F2)] = 0.041 w = 1/[σ2(Fo2) + (0.0534P)2 + 15.0374P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.117Δρmax = 0.66 e Å−3
S = 1.03Δρmin = −1.41 e Å−3
5005 reflectionsAbsolute structure: ?
324 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
H-atom parameters constrained
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
C20.3561 (4)0.3166 (3)0.8608 (3)0.0317 (14)
H20.33800.34350.89640.038*
C60.4433 (4)0.1993 (4)0.6968 (3)0.0337 (14)
H60.49830.21310.68560.040*
C70.2377 (4)−0.0020 (3)0.5639 (2)0.0259 (13)
C80.1506 (4)−0.0082 (3)0.5798 (3)0.0308 (14)
C90.2599 (4)−0.0376 (3)0.5056 (3)0.0305 (14)
C110.4385 (4)0.3222 (3)0.8414 (3)0.0339 (14)
C120.3006 (4)0.2705 (3)0.8270 (3)0.0303 (14)
C140.4154 (5)0.1968 (4)0.5531 (3)0.0493 (19)
H14A0.42860.24920.56900.059*
H14B0.44710.18970.51460.059*
C150.4655 (4)0.2818 (3)0.7888 (3)0.0345 (14)
H150.52170.28540.77620.041*
C160.1130 (4)0.0867 (4)0.7353 (3)0.0429 (17)
H16A0.05210.08340.73020.052*
H16B0.12690.13960.74980.052*
C170.4470 (4)0.1364 (4)0.6005 (3)0.0409 (16)
H17A0.43440.08320.58600.049*
H17B0.50780.14120.60530.049*
C190.1420 (5)0.0261 (4)0.7831 (3)0.0517 (19)
H19A0.10940.03380.82120.062*
H19B0.1284−0.02620.76720.062*
C200.0937 (4)−0.0493 (3)0.5409 (3)0.0336 (14)
H200.0371−0.05340.55230.040*
C210.4089 (4)0.2357 (3)0.7544 (3)0.0305 (13)
C220.1210 (4)−0.0829 (4)0.4868 (3)0.0374 (15)
C230.2340 (5)0.0274 (4)0.8000 (3)0.0460 (17)
H23A0.24680.07840.81880.055*
H23B0.2440−0.01280.83170.055*
C240.3801 (5)0.0185 (4)0.7721 (3)0.0508 (18)
H24A0.3868−0.01960.80520.076*
H24B0.39020.07070.78820.076*
H24C0.41990.00730.73920.076*
C250.3231 (4)0.2284 (3)0.7711 (3)0.0283 (13)
C260.2039 (4)−0.0770 (4)0.4687 (3)0.0364 (15)
H260.2218−0.09980.43120.044*
C270.2824 (4)−0.0665 (3)0.7214 (3)0.0411 (16)
H27A0.2894−0.10480.75430.062*
H27B0.3235−0.07590.68910.062*
H27C0.2266−0.07110.70400.062*
C280.1761 (5)0.2009 (4)0.5649 (3)0.0516 (19)
H28A0.16710.24240.53480.077*
H28B0.13630.20620.59860.077*
H28C0.16850.15040.54480.077*
C290.2727 (5)0.2868 (4)0.6164 (3)0.0471 (18)
H29A0.26730.32530.58350.071*
H29B0.32750.29150.63560.071*
H29C0.22970.29570.64750.071*
C300.3234 (5)0.1949 (4)0.5373 (3)0.0463 (18)
H30A0.31260.23560.50620.056*
H30B0.31120.14420.51780.056*
C310.1173 (4)0.0247 (3)0.6373 (3)0.0333 (14)
H310.06240.01000.64800.040*
N10.1546 (3)0.0715 (3)0.6751 (2)0.0295 (11)
N20.4049 (3)0.1510 (3)0.6611 (2)0.0309 (11)
N30.2629 (3)0.2064 (3)0.5899 (2)0.0353 (12)
N40.2942 (3)0.0139 (3)0.7472 (2)0.0341 (12)
O10.2677 (3)0.1893 (2)0.74031 (17)0.0326 (9)
O30.2936 (2)0.0318 (2)0.59826 (17)0.0292 (9)
Se10.18790 (4)0.26148 (5)0.85594 (3)0.0481 (2)
H1A0.15550.27890.82920.072*
Se20.51657 (5)0.38473 (4)0.88781 (3)0.0482 (2)
H2A0.49280.42480.90060.072*
Se30.37374 (5)−0.02917 (5)0.47921 (3)0.0479 (2)
H3A0.3906−0.07270.46750.072*
Se40.04414 (5)−0.14005 (4)0.43431 (3)0.0517 (2)
H4A0.0342−0.11410.40260.078*
Zn10.27994 (5)0.11131 (4)0.66822 (3)0.0408 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C20.038 (4)0.032 (3)0.025 (3)0.000 (3)0.001 (3)−0.003 (3)
C60.029 (4)0.038 (4)0.035 (3)−0.002 (3)0.001 (3)−0.002 (3)
C70.031 (4)0.021 (3)0.026 (3)0.004 (3)−0.001 (3)0.005 (2)
C80.034 (4)0.027 (3)0.031 (3)0.002 (3)−0.002 (3)0.000 (3)
C90.037 (4)0.025 (3)0.029 (3)0.007 (3)0.001 (3)0.004 (2)
C110.038 (4)0.029 (3)0.035 (3)−0.006 (3)−0.002 (3)−0.001 (3)
C120.032 (3)0.029 (3)0.030 (3)0.003 (3)0.003 (3)0.001 (3)
C140.061 (5)0.048 (4)0.038 (4)−0.007 (4)0.019 (4)−0.001 (3)
C150.026 (3)0.038 (3)0.040 (3)−0.002 (3)0.001 (3)−0.002 (3)
C160.027 (4)0.061 (4)0.041 (4)−0.007 (3)0.009 (3)−0.023 (3)
C170.031 (4)0.051 (4)0.040 (4)0.001 (3)0.012 (3)−0.017 (3)
C190.062 (5)0.060 (5)0.033 (4)−0.013 (4)0.015 (3)−0.004 (3)
C200.029 (4)0.032 (3)0.040 (3)−0.003 (3)−0.003 (3)−0.004 (3)
C210.026 (3)0.033 (3)0.033 (3)−0.002 (3)−0.001 (3)−0.005 (3)
C220.043 (4)0.031 (3)0.038 (4)0.001 (3)−0.009 (3)0.000 (3)
C230.061 (5)0.047 (4)0.030 (3)−0.006 (4)0.002 (3)0.006 (3)
C240.052 (5)0.050 (4)0.050 (4)−0.004 (4)−0.007 (4)0.010 (3)
C250.030 (3)0.025 (3)0.030 (3)−0.002 (3)−0.001 (3)0.001 (3)
C260.052 (4)0.032 (3)0.025 (3)0.008 (3)−0.001 (3)−0.004 (3)
C270.052 (4)0.027 (3)0.044 (4)−0.003 (3)0.002 (3)0.006 (3)
C280.064 (5)0.038 (4)0.053 (4)0.008 (4)−0.005 (4)0.005 (3)
C290.069 (5)0.033 (4)0.039 (4)0.006 (3)0.005 (4)0.002 (3)
C300.064 (5)0.041 (4)0.034 (4)−0.001 (4)0.008 (3)0.001 (3)
C310.026 (3)0.034 (3)0.041 (3)0.000 (3)0.001 (3)0.001 (3)
N10.021 (3)0.035 (3)0.033 (3)−0.002 (2)0.003 (2)−0.005 (2)
N20.023 (3)0.037 (3)0.032 (3)−0.003 (2)0.007 (2)−0.004 (2)
N30.040 (3)0.029 (3)0.037 (3)0.000 (2)−0.001 (2)−0.001 (2)
N40.038 (3)0.031 (3)0.033 (3)−0.005 (2)−0.001 (2)−0.001 (2)
O10.030 (2)0.035 (2)0.033 (2)−0.0030 (19)0.0047 (19)−0.0088 (19)
O30.026 (2)0.032 (2)0.029 (2)−0.0031 (18)−0.0007 (17)−0.0074 (18)
Se10.0359 (4)0.0637 (5)0.0448 (4)−0.0061 (4)0.0120 (3)−0.0130 (4)
Se20.0418 (4)0.0535 (5)0.0492 (4)−0.0096 (3)−0.0053 (3)−0.0182 (3)
Se30.0401 (4)0.0656 (5)0.0379 (4)0.0013 (4)0.0104 (3)−0.0119 (3)
Se40.0552 (5)0.0488 (4)0.0511 (4)0.0001 (4)−0.0231 (4)−0.0151 (3)
Zn10.0388 (5)0.0432 (5)0.0404 (4)−0.0027 (4)0.0028 (4)−0.0059 (3)
Geometric parameters (Å, °) top
C2—C111.370 (8)C22—Se41.912 (6)
C2—C121.376 (8)C23—N41.491 (8)
C2—H20.9300C23—H23A0.9700
C6—N21.269 (7)C23—H23B0.9700
C6—C211.475 (8)C24—N41.461 (8)
C6—H60.9300C24—H24A0.9600
C7—O31.280 (7)C24—H24B0.9600
C7—C81.421 (8)C24—H24C0.9600
C7—C91.423 (8)C25—O11.277 (6)
C8—C201.406 (8)C26—H260.9300
C8—C311.446 (8)C27—N41.476 (7)
C9—C261.359 (8)C27—H27A0.9600
C9—Se31.890 (6)C27—H27B0.9600
C11—C151.378 (8)C27—H27C0.9600
C11—Se21.901 (6)C28—N31.474 (9)
C12—C251.432 (8)C28—H28A0.9600
C12—Se11.892 (6)C28—H28B0.9600
C14—C301.492 (10)C28—H28C0.9600
C14—C171.518 (9)C29—N31.477 (8)
C14—H14A0.9700C29—H29A0.9600
C14—H14B0.9700C29—H29B0.9600
C15—C211.394 (8)C29—H29C0.9600
C15—H150.9300C30—N31.486 (8)
C16—N11.463 (7)C30—H30A0.9700
C16—C191.514 (9)C30—H30B0.9700
C16—H16A0.9700C31—N11.273 (7)
C16—H16B0.9700C31—H310.9300
C17—N21.472 (7)Zn1—N12.096 (5)
C17—H17A0.9700Zn1—N22.092 (5)
C17—H17B0.9700Zn1—N32.330 (5)
C19—C231.499 (10)Zn1—N42.362 (5)
C19—H19A0.9700Zn1—O12.031 (4)
C19—H19B0.9700Zn1—O32.017 (4)
C20—C221.354 (8)Se1—H1A0.8200
C20—H200.9300Se2—H2A0.8200
C21—C251.407 (8)Se3—H3A0.8200
C22—C261.370 (9)Se4—H4A0.8200
C11—C2—C12119.1 (5)C21—C25—C12113.9 (5)
C11—C2—H2120.4C9—C26—C22119.7 (6)
C12—C2—H2120.4C9—C26—H26120.1
N2—C6—C21126.1 (6)C22—C26—H26120.1
N2—C6—H6117.0N4—C27—H27A109.5
C21—C6—H6117.0N4—C27—H27B109.5
O3—C7—C8124.4 (5)H27A—C27—H27B109.5
O3—C7—C9121.1 (5)N4—C27—H27C109.5
C8—C7—C9114.5 (5)H27A—C27—H27C109.5
C20—C8—C7121.1 (5)H27B—C27—H27C109.5
C20—C8—C31117.1 (6)N3—C28—H28A109.5
C7—C8—C31121.8 (5)N3—C28—H28B109.5
C26—C9—C7123.5 (6)H28A—C28—H28B109.5
C26—C9—Se3119.0 (5)N3—C28—H28C109.5
C7—C9—Se3117.6 (4)H28A—C28—H28C109.5
C2—C11—C15120.3 (6)H28B—C28—H28C109.5
C2—C11—Se2119.9 (4)N3—C29—H29A109.5
C15—C11—Se2119.8 (5)N3—C29—H29B109.5
C2—C12—C25123.9 (6)H29A—C29—H29B109.5
C2—C12—Se1118.4 (4)N3—C29—H29C109.5
C25—C12—Se1117.7 (4)H29A—C29—H29C109.5
C30—C14—C17117.2 (6)H29B—C29—H29C109.5
C30—C14—H14A108.0N3—C30—C14117.0 (5)
C17—C14—H14A108.0N3—C30—H30A108.0
C30—C14—H14B108.0C14—C30—H30A108.0
C17—C14—H14B108.0N3—C30—H30B108.0
H14A—C14—H14B107.3C14—C30—H30B108.0
C11—C15—C21120.4 (6)H30A—C30—H30B107.3
C11—C15—H15119.8N1—C31—C8127.2 (6)
C21—C15—H15119.8N1—C31—H31116.4
N1—C16—C19109.6 (5)C8—C31—H31116.4
N1—C16—H16A109.8C31—N1—C16116.9 (5)
C19—C16—H16A109.8C31—N1—Zn1126.4 (4)
N1—C16—H16B109.8C16—N1—Zn1115.5 (4)
C19—C16—H16B109.8C6—N2—C17114.6 (5)
H16A—C16—H16B108.2C6—N2—Zn1127.8 (4)
N2—C17—C14108.7 (5)C17—N2—Zn1115.9 (4)
N2—C17—H17A110.0C28—N3—C29107.1 (5)
C14—C17—H17A110.0C28—N3—C30108.5 (5)
N2—C17—H17B110.0C29—N3—C30109.9 (5)
C14—C17—H17B110.0C28—N3—Zn1108.9 (4)
H17A—C17—H17B108.3C29—N3—Zn1110.3 (4)
C23—C19—C16116.4 (6)C30—N3—Zn1112.0 (4)
C23—C19—H19A108.2C24—N4—C27107.5 (5)
C16—C19—H19A108.2C24—N4—C23108.1 (5)
C23—C19—H19B108.2C27—N4—C23109.9 (5)
C16—C19—H19B108.2C24—N4—Zn1108.1 (4)
H19A—C19—H19B107.3C27—N4—Zn1111.3 (4)
C22—C20—C8120.2 (6)C23—N4—Zn1111.7 (4)
C22—C20—H20119.9C25—O1—Zn1131.0 (4)
C8—C20—H20119.9C7—O3—Zn1130.1 (4)
C15—C21—C25122.3 (5)C12—Se1—H1A109.5
C15—C21—C6115.7 (5)C11—Se2—H2A109.5
C25—C21—C6121.9 (5)C9—Se3—H3A109.5
C20—C22—C26120.9 (6)C22—Se4—H4A109.5
C20—C22—Se4120.4 (5)O3—Zn1—O1178.46 (16)
C26—C22—Se4118.7 (5)O3—Zn1—N293.35 (17)
N4—C23—C19115.8 (5)O1—Zn1—N286.43 (17)
N4—C23—H23A108.3O3—Zn1—N186.55 (17)
C19—C23—H23A108.3O1—Zn1—N193.68 (17)
N4—C23—H23B108.3N2—Zn1—N1179.8 (2)
C19—C23—H23B108.3O3—Zn1—N386.68 (16)
H23A—C23—H23B107.4O1—Zn1—N394.79 (16)
N4—C24—H24A109.5N2—Zn1—N380.60 (19)
N4—C24—H24B109.5N1—Zn1—N399.28 (19)
H24A—C24—H24B109.5O3—Zn1—N493.03 (16)
N4—C24—H24C109.5O1—Zn1—N485.51 (16)
H24A—C24—H24C109.5N2—Zn1—N4100.64 (18)
H24B—C24—H24C109.5N1—Zn1—N479.48 (18)
O1—C25—C21125.2 (5)N3—Zn1—N4178.74 (18)
O1—C25—C12120.9 (5)
Table 1
Selected geometric parameters (Å) top
Zn1—N12.096 (5)Zn1—N42.362 (5)
Zn1—N22.092 (5)Zn1—O12.031 (4)
Zn1—N32.330 (5)Zn1—O32.017 (4)
references
References top

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.

Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands.

Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.

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