Literature DB >> 21577571

4,4',6,6'-Tetra-hydro-seleno-2,2'-[(E,E)-cyclo-hexane-1,2-diylbis(nitrilo-methyl-idyne)]diphenol.

Qiang Wang¹, Ru-Hua Zha, Ji-Wen Yuan, Qing-Fu Zeng.

Abstract

In the title mol-ecule, C(20)H(22)N(2)O(2)Se(4), the dihedral angle between the pendant aromatic rings is 67.1 (2)°. The conformation is stabilized by two intra-molecular O-H⋯N hydrogen bonds.

Entities: CellLine Chemical Disease Species

Year: 2009 PMID： 21577571 PMCID： PMC2969991 DOI： 10.1107/S1600536809031572

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

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 = 638.24 Monoclinic, 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[F 2 > 2σ(F 2)] = 0.041 wR(F 2) = 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 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. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809031572/hb5041sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809031572/hb5041Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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

Enraf–Nonius CAD-4 diffractometer	2743 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.048
graphite	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 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

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.

	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*

	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)

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

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

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

2 in total

1. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

2. Synthesis and antimicrobial activities of Schiff bases derived from 5-chloro-salicylaldehyde.

Authors: Lei Shi; Hui-Ming Ge; Shu-Hua Tan; Huan-Qiu Li; Yong-Chun Song; Hai-Liang Zhu; Ren-Xiang Tan
Journal: Eur J Med Chem Date: 2006-11-29 Impact factor: 6.514

2 in total