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

Wang, Q.; Zha, R.-H.; Yuan, J.-W.; Zeng, Q.-F.

doi:10.1107/S1600536809031572

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page o2163

doi:10.1107/S1600536809031572

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

Qiang Wang,^a Ru-Hua Zha,^a Ji-Wen Yuan ^a and Qing-Fu Zeng ^a ^*

^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 ). For reference structural data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₀H₂₂N₂O₂Se₄
M_r = 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 ) T_min = 0.225, T_max = 0.299 (expected range = 0.153–0.203)
11901 measured reflections
4196 independent reflections
2743 reflections with I > 2σ(I)
R_int = 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
Δρ_max = 0.84 e Å⁻³
Δρ_min = −0.54 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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 ); cell refinement: CAD-4 Software; 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809031572/hb5041sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809031572/hb5041Isup2.hkl

checkCIF report

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.

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

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

C₂₀H₂₂N₂O₂Se₄	F(000) = 1232
M_r = 638.24	D_x = 1.914 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 15.493 (2) Å	θ = 9–12°
b = 9.2975 (15) Å	µ = 6.64 mm⁻¹
c = 16.353 (2) Å	T = 296 K
β = 109.865 (5)°	Block, yellow
V = 2215.4 (5) Å³	0.32 × 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 tube	R_int = 0.048
Graphite monochromator	θ_max = 25.7°, θ_min = 1.4°
ω/2θ scans	h = −18→18
Absorption correction: ψ scan (North et al., 1968)	k = −9→11
T_min = 0.225, T_max = 0.299	l = −19→19
11901 measured reflections	3 standard reflections every 200 reflections
4196 independent reflections	intensity decay: 1%

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.105	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0494P)²] where P = (F_o² + 2F_c²)/3
4196 reflections	(Δ/σ)_max = 0.001
255 parameters	Δρ_max = 0.84 e Å⁻³
0 restraints	Δρ_min = −0.54 e Å⁻³

Crystal data top

C₂₀H₂₂N₂O₂Se₄	V = 2215.4 (5) Å³
M_r = 638.24	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.493 (2) Å	µ = 6.64 mm⁻¹
b = 9.2975 (15) Å	T = 296 K
c = 16.353 (2) Å	0.32 × 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)	R_int = 0.048
T_min = 0.225, T_max = 0.299	3 standard reflections every 200 reflections
11901 measured reflections	intensity decay: 1%
4196 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.105	H-atom parameters constrained
S = 1.06	Δρ_max = 0.84 e Å⁻³
4196 reflections	Δρ_min = −0.54 e Å⁻³
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

	x	y	z	U_iso*/U_eq
Se1	1.08983 (4)	0.95743 (7)	1.27220 (3)	0.0629 (2)
Se2	0.64176 (5)	0.45492 (8)	1.21754 (4)	0.0694 (2)
Se3	0.87275 (4)	1.30994 (6)	1.00077 (4)	0.0618 (2)
Se4	0.38089 (4)	0.88004 (8)	1.06267 (4)	0.0683 (2)
O2	0.8152 (2)	1.0256 (4)	0.9129 (2)	0.0464 (9)
H2A	0.8043	0.9482	0.8874	0.070*
C20	0.8744 (3)	0.7422 (5)	0.9727 (3)	0.0397 (11)
H20	0.8937	0.6520	0.9965	0.048*
N2	0.8211 (2)	0.7512 (4)	0.8942 (2)	0.0400 (10)
N1	0.6651 (3)	0.5930 (4)	0.8980 (2)	0.0414 (10)
O1	0.6862 (2)	0.4896 (4)	1.0525 (2)	0.0544 (9)
H1	0.6915	0.4905	1.0043	0.082*
C8	0.9110 (3)	1.1261 (5)	1.0457 (3)	0.0373 (11)
C2	0.5888 (3)	0.5808 (5)	1.1248 (3)	0.0414 (12)
C17	0.6070 (3)	0.6798 (6)	0.9083 (3)	0.0412 (12)
H17	0.5811	0.7480	0.8654	0.049*
C9	0.9725 (3)	1.1108 (5)	1.1272 (3)	0.0399 (12)
H9	0.9948	1.1914	1.1616	0.048*
C10	1.0019 (3)	0.9748 (6)	1.1593 (3)	0.0388 (12)
C11	0.9058 (3)	0.8696 (5)	1.0263 (3)	0.0341 (11)
C3	0.6196 (3)	0.5804 (5)	1.0534 (3)	0.0384 (12)
C18	0.7924 (3)	0.6202 (5)	0.8436 (3)	0.0383 (11)
H18	0.8229	0.5374	0.8786	0.046*
C4	0.4792 (3)	0.7638 (6)	1.0590 (3)	0.0441 (13)
C5	0.5092 (3)	0.7665 (6)	0.9892 (3)	0.0448 (13)
H5	0.4822	0.8297	0.9435	0.054*
C6	0.5190 (3)	0.6701 (6)	1.1264 (3)	0.0431 (13)
H6	0.4983	0.6672	1.1735	0.052*
C7	0.5788 (3)	0.6770 (5)	0.9855 (3)	0.0384 (12)
C12	0.8760 (3)	1.0062 (5)	0.9929 (3)	0.0343 (11)
C19	0.6881 (3)	0.6039 (5)	0.8186 (3)	0.0381 (12)
H19	0.6579	0.6888	0.7856	0.046*
C13	0.9695 (3)	0.8555 (5)	1.1101 (3)	0.0391 (11)
H13	0.9899	0.7648	1.1322	0.047*
C21	0.8179 (3)	0.6275 (6)	0.7615 (3)	0.0564 (15)
H21A	0.7892	0.7109	0.7275	0.068*
H21B	0.8839	0.6378	0.7773	0.068*
C22	0.6558 (4)	0.4706 (6)	0.7630 (3)	0.0545 (15)
H22A	0.6815	0.3860	0.7974	0.065*
H22B	0.5895	0.4642	0.7454	0.065*
C23	0.7866 (3)	0.4919 (6)	0.7072 (4)	0.0566 (16)
H23A	0.8183	0.4091	0.7398	0.068*
H23B	0.8021	0.4990	0.6546	0.068*
C24	0.6834 (3)	0.4719 (6)	0.6833 (3)	0.0553 (15)
H24A	0.6517	0.5494	0.6451	0.066*
H24B	0.6652	0.3819	0.6521	0.066*
H2D	0.6487	0.3556	1.1959	0.066*
H3D	0.8639	1.2980	0.9337	0.066*
H1D	1.0891	0.9500	1.3302	0.066*
H4D	0.3812	0.8789	1.1309	0.066*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Se1	0.0686 (4)	0.0697 (5)	0.0371 (3)	−0.0124 (3)	0.0004 (3)	0.0052 (3)
Se2	0.0850 (5)	0.0807 (5)	0.0424 (3)	0.0074 (4)	0.0217 (3)	0.0183 (3)
Se3	0.0805 (4)	0.0374 (3)	0.0620 (4)	0.0104 (3)	0.0170 (3)	0.0004 (3)
Se4	0.0677 (4)	0.0887 (5)	0.0628 (4)	0.0210 (4)	0.0410 (3)	−0.0011 (3)
O2	0.049 (2)	0.046 (2)	0.0379 (19)	0.0044 (19)	0.0062 (17)	−0.0063 (16)
C20	0.043 (3)	0.031 (3)	0.048 (3)	0.002 (2)	0.019 (3)	0.002 (2)
N2	0.035 (2)	0.045 (3)	0.042 (2)	−0.003 (2)	0.0160 (19)	−0.005 (2)
N1	0.042 (2)	0.054 (3)	0.034 (2)	−0.001 (2)	0.0202 (19)	−0.003 (2)
O1	0.055 (2)	0.067 (3)	0.046 (2)	0.014 (2)	0.0226 (19)	0.0060 (19)
C8	0.042 (3)	0.037 (3)	0.036 (3)	0.000 (2)	0.017 (2)	0.002 (2)
C2	0.043 (3)	0.052 (3)	0.028 (2)	−0.012 (3)	0.011 (2)	−0.001 (2)
C17	0.040 (3)	0.057 (4)	0.028 (2)	−0.002 (3)	0.013 (2)	0.001 (2)
C9	0.046 (3)	0.035 (3)	0.047 (3)	−0.005 (3)	0.026 (3)	−0.006 (2)
C10	0.034 (3)	0.052 (3)	0.033 (3)	−0.003 (3)	0.013 (2)	0.001 (2)
C11	0.032 (2)	0.038 (3)	0.035 (3)	−0.003 (2)	0.014 (2)	−0.005 (2)
C3	0.034 (3)	0.048 (3)	0.033 (3)	−0.008 (2)	0.011 (2)	−0.006 (2)
C18	0.036 (3)	0.037 (3)	0.043 (3)	−0.002 (2)	0.015 (2)	−0.009 (2)
C4	0.044 (3)	0.055 (3)	0.042 (3)	−0.003 (3)	0.025 (2)	−0.005 (3)
C5	0.043 (3)	0.060 (4)	0.034 (3)	0.005 (3)	0.016 (2)	0.003 (2)
C6	0.045 (3)	0.057 (4)	0.033 (3)	−0.011 (3)	0.021 (2)	−0.006 (3)
C7	0.033 (3)	0.054 (3)	0.030 (2)	−0.003 (2)	0.013 (2)	−0.005 (2)
C12	0.033 (3)	0.040 (3)	0.036 (3)	0.005 (2)	0.019 (2)	−0.001 (2)
C19	0.036 (3)	0.052 (3)	0.030 (2)	−0.005 (2)	0.015 (2)	−0.004 (2)
C13	0.043 (3)	0.037 (3)	0.039 (3)	0.000 (3)	0.015 (2)	0.003 (2)
C21	0.047 (3)	0.073 (4)	0.065 (3)	−0.020 (3)	0.040 (3)	−0.023 (3)
C22	0.052 (3)	0.071 (4)	0.049 (3)	−0.023 (3)	0.029 (3)	−0.018 (3)
C23	0.056 (3)	0.070 (4)	0.055 (3)	−0.012 (3)	0.034 (3)	−0.027 (3)
C24	0.057 (3)	0.074 (4)	0.043 (3)	−0.018 (3)	0.028 (3)	−0.019 (3)

Geometric parameters (Å, º) top

Se1—C10	1.893 (5)	C10—C13	1.362 (7)
Se1—H1D	0.9542	C11—C13	1.396 (6)
Se2—C2	1.869 (5)	C11—C12	1.398 (6)
Se2—H2D	1.0078	C3—C7	1.400 (6)
Se3—C8	1.875 (5)	C18—C21	1.524 (6)
Se3—H3D	1.0645	C18—C19	1.534 (6)
Se4—C4	1.885 (5)	C18—H18	0.9800
Se4—H4D	1.1136	C4—C5	1.372 (6)
O2—C12	1.340 (5)	C4—C6	1.376 (7)
O2—H2A	0.8200	C5—C7	1.380 (6)
C20—N2	1.271 (6)	C5—H5	0.9300
C20—C11	1.455 (7)	C6—H6	0.9300
C20—H20	0.9300	C19—C22	1.518 (7)
N2—C18	1.455 (6)	C19—H19	0.9800
N1—C17	1.262 (6)	C13—H13	0.9300
N1—C19	1.461 (5)	C21—C23	1.523 (7)
O1—C3	1.337 (6)	C21—H21A	0.9700
O1—H1	0.8200	C21—H21B	0.9700
C8—C9	1.357 (6)	C22—C24	1.503 (6)
C8—C12	1.402 (6)	C22—H22A	0.9700
C2—C6	1.371 (6)	C22—H22B	0.9700
C2—C3	1.404 (6)	C23—C24	1.524 (7)
C17—C7	1.470 (6)	C23—H23A	0.9700
C17—H17	0.9300	C23—H23B	0.9700
C9—C10	1.385 (7)	C24—H24A	0.9700
C9—H9	0.9300	C24—H24B	0.9700

C10—Se1—H1D	136.7	C7—C5—H5	119.4
C2—Se2—H2D	111.0	C2—C6—C4	120.7 (4)
C8—Se3—H3D	102.8	C2—C6—H6	119.7
C4—Se4—H4D	107.3	C4—C6—H6	119.7
C12—O2—H2A	109.5	C5—C7—C3	120.1 (4)
N2—C20—C11	121.6 (5)	C5—C7—C17	119.4 (4)
N2—C20—H20	119.2	C3—C7—C17	120.4 (4)
C11—C20—H20	119.2	O2—C12—C11	122.2 (4)
C20—N2—C18	119.2 (4)	O2—C12—C8	119.4 (4)
C17—N1—C19	118.3 (4)	C11—C12—C8	118.3 (4)
C3—O1—H1	109.5	N1—C19—C22	110.2 (4)
C9—C8—C12	121.1 (5)	N1—C19—C18	108.9 (4)
C9—C8—Se3	120.3 (4)	C22—C19—C18	110.1 (4)
C12—C8—Se3	118.6 (3)	N1—C19—H19	109.2
C6—C2—C3	120.7 (4)	C22—C19—H19	109.2
C6—C2—Se2	119.7 (3)	C18—C19—H19	109.2
C3—C2—Se2	119.6 (4)	C10—C13—C11	120.0 (5)
N1—C17—C7	122.5 (4)	C10—C13—H13	120.0
N1—C17—H17	118.8	C11—C13—H13	120.0
C7—C17—H17	118.8	C23—C21—C18	110.5 (4)
C8—C9—C10	119.9 (5)	C23—C21—H21A	109.5
C8—C9—H9	120.0	C18—C21—H21A	109.5
C10—C9—H9	120.0	C23—C21—H21B	109.5
C13—C10—C9	120.8 (4)	C18—C21—H21B	109.5
C13—C10—Se1	120.4 (4)	H21A—C21—H21B	108.1
C9—C10—Se1	118.8 (4)	C24—C22—C19	112.3 (4)
C13—C11—C12	119.9 (4)	C24—C22—H22A	109.1
C13—C11—C20	119.7 (5)	C19—C22—H22A	109.1
C12—C11—C20	120.4 (4)	C24—C22—H22B	109.1
O1—C3—C7	122.6 (4)	C19—C22—H22B	109.1
O1—C3—C2	119.4 (4)	H22A—C22—H22B	107.9
C7—C3—C2	118.0 (4)	C21—C23—C24	110.4 (4)
N2—C18—C21	110.1 (4)	C21—C23—H23A	109.6
N2—C18—C19	108.9 (4)	C24—C23—H23A	109.6
C21—C18—C19	109.6 (4)	C21—C23—H23B	109.6
N2—C18—H18	109.4	C24—C23—H23B	109.6
C21—C18—H18	109.4	H23A—C23—H23B	108.1
C19—C18—H18	109.4	C22—C24—C23	111.2 (4)
C5—C4—C6	119.5 (4)	C22—C24—H24A	109.4
C5—C4—Se4	121.5 (4)	C23—C24—H24A	109.4
C6—C4—Se4	119.0 (3)	C22—C24—H24B	109.4
C4—C5—C7	121.1 (5)	C23—C24—H24B	109.4
C4—C5—H5	119.4	H24A—C24—H24B	108.0

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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

Experimental details

Crystal data
Chemical formula	C₂₀H₂₂N₂O₂Se₄
M_r	638.24
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	15.493 (2), 9.2975 (15), 16.353 (2)
β (°)	109.865 (5)
V (Å³)	2215.4 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	6.64
Crystal size (mm)	0.32 × 0.28 × 0.24

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.225, 0.299
No. of measured, independent and observed [I > 2σ(I)] reflections	11901, 4196, 2743
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.610

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.105, 1.06
No. of reflections	4196
No. of parameters	255
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	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

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

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Volume 65| Part 9| September 2009| Page o2163

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

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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