organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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4,4′,6,6′-Tetra­hydro­seleno-2,2′-[(E,E)-cyclo­hexane-1,2-diylbis(nitrilo­methyl­­idyne)]diphenol

aEngineering Research Center for Clean Production of Textile Dyeing and Printing, Ministry of Education, Wuhan 430073, People's Republic of China
*Correspondence e-mail: qfzeng@wuse.edu.cn

(Received 10 August 2009; accepted 11 August 2009; online 15 August 2009)

In the title mol­ecule, C20H22N2O2Se4, the dihedral angle between the pendant aromatic rings is 67.1 (2)°. The conformation is stabilized by two intra­molecular O—H⋯N hydrogen bonds.

Related literature

For background to the biological activity of Schiff base compounds, see: Shi et al. (2007[Shi, L., Ge, H.-M., Tan, S.-H., Li, H.-Q., Song, Y.-C., Zhu, H.-L. & Tan, R.-X. (2007). Eur. J. Med. Chem. 42, 558-564.]). For reference structural data, see: Allen et al. (1987[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.]).

[Scheme 1]

Experimental

Crystal data
  • C20H22N2O2Se4

  • Mr = 638.24

  • Monoclinic, P 21 /c

  • a = 15.493 (2) Å

  • b = 9.2975 (15) Å

  • c = 16.353 (2) Å

  • β = 109.865 (5)°

  • V = 2215.4 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 6.64 mm−1

  • T = 296 K

  • 0.32 × 0.28 × 0.24 mm

Data collection
  • Enraf–Nonius CAD-4 diffractometer

  • Absorption correction: ψ scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.225, Tmax = 0.299 (expected range = 0.153–0.203)

  • 11901 measured reflections

  • 4196 independent reflections

  • 2743 reflections with I > 2σ(I)

  • Rint = 0.048

  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement
  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 0.105

  • S = 1.06

  • 4196 reflections

  • 255 parameters

  • H-atom parameters constrained

  • Δρmax = 0.84 e Å−3

  • Δρmin = −0.54 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O2—H2A⋯N2 0.82 1.85 2.575 (5) 147
O1—H1⋯N1 0.82 1.90 2.619 (5) 145

Data collection: CAD-4 Software (Enraf–Nonius, 1989[Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

There has been much research interest in Schiff base compounds due to their biological activities (Shi et al., 2007). 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). There are two intramolecular O—H···N hydrogen bonds in (I) (Table 1).

Related literature top

For background to the biological activity of Schiff base compounds, see: Shi et al. (2007). For reference structural data, see: Allen et al. (1987);

Experimental top

A mixture of 3,5-dihydroseleno-2-hydroxybenzaldehyde (564 mg, 2 mmol) and cyclohexane-1,2-diamine (114 mg, 1 mmol) in methanol (10 ml) was stirred for 2 h. After keeping the filtrate in air for 5 d, yellow blocks of (I) were formed.

Refinement top

The Se bound H atoms were located in a difference map and refined as riding in their as-found relative positions. The C-bound H atoms were positioned geometrically (C—H = 0.93 Å for the aromatic H atoms and C—H = 0.96 Å for the aliphatic H atoms) and were refined as riding, with Uiso(H) = 1.2Ueq(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.
4,4',6,6'-Tetrahydroseleno-2,2'-[(E,E)-cyclohexane-1,2- diylbis(nitrilomethylidyne)]diphenol top
Crystal data top
C20H22N2O2Se4F(000) = 1232
Mr = 638.24Dx = 1.914 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 15.493 (2) Åθ = 9–12°
b = 9.2975 (15) ŵ = 6.64 mm1
c = 16.353 (2) ÅT = 296 K
β = 109.865 (5)°Block, yellow
V = 2215.4 (5) Å30.32 × 0.28 × 0.24 mm
Z = 4
Data collection top
Enraf–Nonius CAD-4
diffractometer
2743 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.048
Graphite monochromatorθmax = 25.7°, θmin = 1.4°
ω/2θ scansh = 1818
Absorption correction: ψ scan
(North et al., 1968)
k = 911
Tmin = 0.225, Tmax = 0.299l = 1919
11901 measured reflections3 standard reflections every 200 reflections
4196 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) = 0.105H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0494P)2]
where P = (Fo2 + 2Fc2)/3
4196 reflections(Δ/σ)max = 0.001
255 parametersΔρmax = 0.84 e Å3
0 restraintsΔρmin = 0.54 e Å3
Crystal data top
C20H22N2O2Se4V = 2215.4 (5) Å3
Mr = 638.24Z = 4
Monoclinic, P21/cMo Kα radiation
a = 15.493 (2) ŵ = 6.64 mm1
b = 9.2975 (15) ÅT = 296 K
c = 16.353 (2) Å0.32 × 0.28 × 0.24 mm
β = 109.865 (5)°
Data collection top
Enraf–Nonius CAD-4
diffractometer
2743 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.048
Tmin = 0.225, Tmax = 0.2993 standard reflections every 200 reflections
11901 measured reflections intensity decay: 1%
4196 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.105H-atom parameters constrained
S = 1.06Δρmax = 0.84 e Å3
4196 reflectionsΔρmin = 0.54 e Å3
255 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
Se11.08983 (4)0.95743 (7)1.27220 (3)0.0629 (2)
Se20.64176 (5)0.45492 (8)1.21754 (4)0.0694 (2)
Se30.87275 (4)1.30994 (6)1.00077 (4)0.0618 (2)
Se40.38089 (4)0.88004 (8)1.06267 (4)0.0683 (2)
O20.8152 (2)1.0256 (4)0.9129 (2)0.0464 (9)
H2A0.80430.94820.88740.070*
C200.8744 (3)0.7422 (5)0.9727 (3)0.0397 (11)
H200.89370.65200.99650.048*
N20.8211 (2)0.7512 (4)0.8942 (2)0.0400 (10)
N10.6651 (3)0.5930 (4)0.8980 (2)0.0414 (10)
O10.6862 (2)0.4896 (4)1.0525 (2)0.0544 (9)
H10.69150.49051.00430.082*
C80.9110 (3)1.1261 (5)1.0457 (3)0.0373 (11)
C20.5888 (3)0.5808 (5)1.1248 (3)0.0414 (12)
C170.6070 (3)0.6798 (6)0.9083 (3)0.0412 (12)
H170.58110.74800.86540.049*
C90.9725 (3)1.1108 (5)1.1272 (3)0.0399 (12)
H90.99481.19141.16160.048*
C101.0019 (3)0.9748 (6)1.1593 (3)0.0388 (12)
C110.9058 (3)0.8696 (5)1.0263 (3)0.0341 (11)
C30.6196 (3)0.5804 (5)1.0534 (3)0.0384 (12)
C180.7924 (3)0.6202 (5)0.8436 (3)0.0383 (11)
H180.82290.53740.87860.046*
C40.4792 (3)0.7638 (6)1.0590 (3)0.0441 (13)
C50.5092 (3)0.7665 (6)0.9892 (3)0.0448 (13)
H50.48220.82970.94350.054*
C60.5190 (3)0.6701 (6)1.1264 (3)0.0431 (13)
H60.49830.66721.17350.052*
C70.5788 (3)0.6770 (5)0.9855 (3)0.0384 (12)
C120.8760 (3)1.0062 (5)0.9929 (3)0.0343 (11)
C190.6881 (3)0.6039 (5)0.8186 (3)0.0381 (12)
H190.65790.68880.78560.046*
C130.9695 (3)0.8555 (5)1.1101 (3)0.0391 (11)
H130.98990.76481.13220.047*
C210.8179 (3)0.6275 (6)0.7615 (3)0.0564 (15)
H21A0.78920.71090.72750.068*
H21B0.88390.63780.77730.068*
C220.6558 (4)0.4706 (6)0.7630 (3)0.0545 (15)
H22A0.68150.38600.79740.065*
H22B0.58950.46420.74540.065*
C230.7866 (3)0.4919 (6)0.7072 (4)0.0566 (16)
H23A0.81830.40910.73980.068*
H23B0.80210.49900.65460.068*
C240.6834 (3)0.4719 (6)0.6833 (3)0.0553 (15)
H24A0.65170.54940.64510.066*
H24B0.66520.38190.65210.066*
H2D0.64870.35561.19590.066*
H3D0.86391.29800.93370.066*
H1D1.08910.95001.33020.066*
H4D0.38120.87891.13090.066*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Se10.0686 (4)0.0697 (5)0.0371 (3)0.0124 (3)0.0004 (3)0.0052 (3)
Se20.0850 (5)0.0807 (5)0.0424 (3)0.0074 (4)0.0217 (3)0.0183 (3)
Se30.0805 (4)0.0374 (3)0.0620 (4)0.0104 (3)0.0170 (3)0.0004 (3)
Se40.0677 (4)0.0887 (5)0.0628 (4)0.0210 (4)0.0410 (3)0.0011 (3)
O20.049 (2)0.046 (2)0.0379 (19)0.0044 (19)0.0062 (17)0.0063 (16)
C200.043 (3)0.031 (3)0.048 (3)0.002 (2)0.019 (3)0.002 (2)
N20.035 (2)0.045 (3)0.042 (2)0.003 (2)0.0160 (19)0.005 (2)
N10.042 (2)0.054 (3)0.034 (2)0.001 (2)0.0202 (19)0.003 (2)
O10.055 (2)0.067 (3)0.046 (2)0.014 (2)0.0226 (19)0.0060 (19)
C80.042 (3)0.037 (3)0.036 (3)0.000 (2)0.017 (2)0.002 (2)
C20.043 (3)0.052 (3)0.028 (2)0.012 (3)0.011 (2)0.001 (2)
C170.040 (3)0.057 (4)0.028 (2)0.002 (3)0.013 (2)0.001 (2)
C90.046 (3)0.035 (3)0.047 (3)0.005 (3)0.026 (3)0.006 (2)
C100.034 (3)0.052 (3)0.033 (3)0.003 (3)0.013 (2)0.001 (2)
C110.032 (2)0.038 (3)0.035 (3)0.003 (2)0.014 (2)0.005 (2)
C30.034 (3)0.048 (3)0.033 (3)0.008 (2)0.011 (2)0.006 (2)
C180.036 (3)0.037 (3)0.043 (3)0.002 (2)0.015 (2)0.009 (2)
C40.044 (3)0.055 (3)0.042 (3)0.003 (3)0.025 (2)0.005 (3)
C50.043 (3)0.060 (4)0.034 (3)0.005 (3)0.016 (2)0.003 (2)
C60.045 (3)0.057 (4)0.033 (3)0.011 (3)0.021 (2)0.006 (3)
C70.033 (3)0.054 (3)0.030 (2)0.003 (2)0.013 (2)0.005 (2)
C120.033 (3)0.040 (3)0.036 (3)0.005 (2)0.019 (2)0.001 (2)
C190.036 (3)0.052 (3)0.030 (2)0.005 (2)0.015 (2)0.004 (2)
C130.043 (3)0.037 (3)0.039 (3)0.000 (3)0.015 (2)0.003 (2)
C210.047 (3)0.073 (4)0.065 (3)0.020 (3)0.040 (3)0.023 (3)
C220.052 (3)0.071 (4)0.049 (3)0.023 (3)0.029 (3)0.018 (3)
C230.056 (3)0.070 (4)0.055 (3)0.012 (3)0.034 (3)0.027 (3)
C240.057 (3)0.074 (4)0.043 (3)0.018 (3)0.028 (3)0.019 (3)
Geometric parameters (Å, º) top
Se1—C101.893 (5)C10—C131.362 (7)
Se1—H1D0.9542C11—C131.396 (6)
Se2—C21.869 (5)C11—C121.398 (6)
Se2—H2D1.0078C3—C71.400 (6)
Se3—C81.875 (5)C18—C211.524 (6)
Se3—H3D1.0645C18—C191.534 (6)
Se4—C41.885 (5)C18—H180.9800
Se4—H4D1.1136C4—C51.372 (6)
O2—C121.340 (5)C4—C61.376 (7)
O2—H2A0.8200C5—C71.380 (6)
C20—N21.271 (6)C5—H50.9300
C20—C111.455 (7)C6—H60.9300
C20—H200.9300C19—C221.518 (7)
N2—C181.455 (6)C19—H190.9800
N1—C171.262 (6)C13—H130.9300
N1—C191.461 (5)C21—C231.523 (7)
O1—C31.337 (6)C21—H21A0.9700
O1—H10.8200C21—H21B0.9700
C8—C91.357 (6)C22—C241.503 (6)
C8—C121.402 (6)C22—H22A0.9700
C2—C61.371 (6)C22—H22B0.9700
C2—C31.404 (6)C23—C241.524 (7)
C17—C71.470 (6)C23—H23A0.9700
C17—H170.9300C23—H23B0.9700
C9—C101.385 (7)C24—H24A0.9700
C9—H90.9300C24—H24B0.9700
C10—Se1—H1D136.7C7—C5—H5119.4
C2—Se2—H2D111.0C2—C6—C4120.7 (4)
C8—Se3—H3D102.8C2—C6—H6119.7
C4—Se4—H4D107.3C4—C6—H6119.7
C12—O2—H2A109.5C5—C7—C3120.1 (4)
N2—C20—C11121.6 (5)C5—C7—C17119.4 (4)
N2—C20—H20119.2C3—C7—C17120.4 (4)
C11—C20—H20119.2O2—C12—C11122.2 (4)
C20—N2—C18119.2 (4)O2—C12—C8119.4 (4)
C17—N1—C19118.3 (4)C11—C12—C8118.3 (4)
C3—O1—H1109.5N1—C19—C22110.2 (4)
C9—C8—C12121.1 (5)N1—C19—C18108.9 (4)
C9—C8—Se3120.3 (4)C22—C19—C18110.1 (4)
C12—C8—Se3118.6 (3)N1—C19—H19109.2
C6—C2—C3120.7 (4)C22—C19—H19109.2
C6—C2—Se2119.7 (3)C18—C19—H19109.2
C3—C2—Se2119.6 (4)C10—C13—C11120.0 (5)
N1—C17—C7122.5 (4)C10—C13—H13120.0
N1—C17—H17118.8C11—C13—H13120.0
C7—C17—H17118.8C23—C21—C18110.5 (4)
C8—C9—C10119.9 (5)C23—C21—H21A109.5
C8—C9—H9120.0C18—C21—H21A109.5
C10—C9—H9120.0C23—C21—H21B109.5
C13—C10—C9120.8 (4)C18—C21—H21B109.5
C13—C10—Se1120.4 (4)H21A—C21—H21B108.1
C9—C10—Se1118.8 (4)C24—C22—C19112.3 (4)
C13—C11—C12119.9 (4)C24—C22—H22A109.1
C13—C11—C20119.7 (5)C19—C22—H22A109.1
C12—C11—C20120.4 (4)C24—C22—H22B109.1
O1—C3—C7122.6 (4)C19—C22—H22B109.1
O1—C3—C2119.4 (4)H22A—C22—H22B107.9
C7—C3—C2118.0 (4)C21—C23—C24110.4 (4)
N2—C18—C21110.1 (4)C21—C23—H23A109.6
N2—C18—C19108.9 (4)C24—C23—H23A109.6
C21—C18—C19109.6 (4)C21—C23—H23B109.6
N2—C18—H18109.4C24—C23—H23B109.6
C21—C18—H18109.4H23A—C23—H23B108.1
C19—C18—H18109.4C22—C24—C23111.2 (4)
C5—C4—C6119.5 (4)C22—C24—H24A109.4
C5—C4—Se4121.5 (4)C23—C24—H24A109.4
C6—C4—Se4119.0 (3)C22—C24—H24B109.4
C4—C5—C7121.1 (5)C23—C24—H24B109.4
C4—C5—H5119.4H24A—C24—H24B108.0
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2A···N20.821.852.575 (5)147
O1—H1···N10.821.902.619 (5)145

Experimental details

Crystal data
Chemical formulaC20H22N2O2Se4
Mr638.24
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)15.493 (2), 9.2975 (15), 16.353 (2)
β (°) 109.865 (5)
V3)2215.4 (5)
Z4
Radiation typeMo Kα
µ (mm1)6.64
Crystal size (mm)0.32 × 0.28 × 0.24
Data collection
DiffractometerEnraf–Nonius CAD-4
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.225, 0.299
No. of measured, independent and
observed [I > 2σ(I)] reflections
11901, 4196, 2743
Rint0.048
(sin θ/λ)max1)0.610
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.105, 1.06
No. of reflections4196
No. of parameters255
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.84, 0.54

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2A···N20.821.852.575 (5)147
O1—H1···N10.821.902.619 (5)145
 

Acknowledgements

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).

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science
First citationEnraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands.
First citationHarms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
First citationNorth, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.  CrossRef IUCr Journals Web of Science
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationShi, L., Ge, H.-M., Tan, S.-H., Li, H.-Q., Song, Y.-C., Zhu, H.-L. & Tan, R.-X. (2007). Eur. J. Med. Chem. 42, 558–564.  Web of Science CrossRef PubMed CAS

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