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Acta Crystallogr Sect E Struct Rep Online. 2009 September 1; 65(Pt 9): m1090.
Published online 2009 August 19. doi:  10.1107/S1600536809032061
PMCID: PMC2969977

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

Abstract

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.

Related literature

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

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Object name is e-65-m1090-scheme1.jpg

Experimental

Crystal data

  • [Zn(C12H17N2OSe2)2]
  • M r = 791.76
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-m1090-efi1.jpg
  • a = 15.8066 (16) Å
  • b = 16.875 (3) Å
  • c = 21.297 (3) Å
  • V = 5680.4 (13) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 6.02 mm−1
  • T = 296 K
  • 0.35 × 0.28 × 0.24 mm

Data collection

  • Enraf–Nonius CAD-4 diffractometer
  • Absorption correction: ψ scan (North et al., 1968 [triangle]) T min = 0.227, T max = 0.326 (expected range = 0.164–0.236)
  • 28494 measured reflections
  • 5005 independent reflections
  • 3434 reflections with I > 2σ(I)
  • R int = 0.064
  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement

  • R[F 2 > 2σ(F 2)] = 0.041
  • wR(F 2) = 0.117
  • S = 1.03
  • 5005 reflections
  • 324 parameters
  • H-atom parameters constrained
  • Δρmax = 0.66 e Å−3
  • Δρmin = −1.41 e Å−3

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

Table 1
Selected bond lengths (Å)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809032061/hb5046sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809032061/hb5046Isup2.hkl

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

Acknowledgments

The project was supported by the Scientific Research Foundation for Returned Overseas Chinese Scholars, State Education Ministry, Educational Commission of Hubei Province (D20091703) and the Natural Science Foundation of Hubei Province (2008CDB038).

supplementary crystallographic information

Comment

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).

Experimental

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

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).

Figures

Fig. 1.
The molecular structure of (I) showing 30% probability displacement ellipsoids.

Crystal data

[Zn(C12H17N2OSe2)2]F(000) = 3104
Mr = 791.76Dx = 1.852 Mg m3
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 mm1
c = 21.297 (3) ÅT = 296 K
V = 5680.4 (13) Å3Block, colourless
Z = 80.35 × 0.28 × 0.24 mm

Data collection

Enraf–Nonius CAD-4 diffractometer3434 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

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 = 1.03w = 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 Å3
0 restraintsΔρmin = −1.41 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
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)

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, °)

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)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5046).

References

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