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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 3| March 2010| Page o512
doi:10.1107/S1600536810003430

6,6′-Dieth­­oxy-2,2′-[propane-1,3-diyl­di­oxy­bis­(nitrilo­methyl­­idyne)]diphenol

Li Wang,a* Yin-Xia Suna and Jun-Feng Tonga

aSchool of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, People's Republic of China
*Correspondence e-mail: wangl@mail.lzjtu.cn

(Received 19 January 2010; accepted 28 January 2010; online 3 February 2010)

The complete mol­ecule of the title compound, C21H26N2O6, is generated by a crystallographic twofold axis and adopts a trans configuration with respect to the azomethine group. The two benzene rings are almost perpendicular to one another, making a dihedral angle of 89.53 (3)°. In the mol­ecular structure, pairs of intra­molecular O—H⋯N hydrogen bonds generate two six-membered rings. The crystal structure is further stabilized by inter­molecular C—H⋯O hydrogen bonds, which link four adjacent mol­ecules into a network structure.

Related literature

For background to salen-type bis­oxime compounds, see: Dong et al. (2007a[Dong, W.-K., Duan, J.-G. & Liu, G.-L. (2007a). Transition Met. Chem. 32, 702-705.],b[Dong, W.-K., Feng, J.-H. & Yang, X.-Q. (2007b). Synth. React. Inorg. Met. Org. Nano-Chem. 37, 61-65.]; Dong & Duan, 2008[Dong, W.-K. & Duan, J.-G. (2008). J. Coord. Chem. 61, 781-788.]). For the synthesis, see: Dong et al. (2008[Dong, W.-K., Zhang, Y.-P., Zhao, C.-Y., Tang, X.-L., Lv, Z.-W. & Zou, Z. (2008). Chin. J. Chem. 21, 1821-1825.], 2009[Dong, W.-K., He, X.-N., Yan, H.-B., Lv, Z.-W., Chen, X., Zhao, C.-Y. & Tang, X.-L. (2009). Polyhedron, 28, 1419-1428.]). For background to hydrogen bonding, see: Desiraju (1996[Desiraju, G. R. (1996). Acc. Chem. Res. 29, 441-449.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N. L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data

  • C21H26N2O6

  • Mr = 402.44

  • Orthorhombic, F d d 2

  • a = 25.292 (2) Å

  • b = 34.412 (3) Å

  • c = 4.7176 (5) Å

  • V = 4105.9 (7) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 298 K

  • 0.45 × 0.18 × 0.17 mm
Data collection

  • Bruker SMART 1000 CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.958, Tmax = 0.984

  • 5348 measured reflections

  • 1031 independent reflections

  • 817 reflections with I > 2σ(I)

  • Rint = 0.048
Refinement

  • R[F2 > 2σ(F2)] = 0.037

  • wR(F2) = 0.090

  • S = 1.04

  • 1031 reflections

  • 133 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.16 e Å−3

  • Δρmin = −0.14 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O2—H2⋯N1 0.82 1.92 2.636 (2) 145
C11—H11C⋯O1i 0.96 2.57 3.410 (3) 146
Symmetry code: (i) [x+{\script{1\over 4}}, -y+{\script{1\over 4}}, z+{\script{5\over 4}}].

Data collection: SMART (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810003430/hg2634sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810003430/hg2634Isup2.hkl

checkCIF report


Comment top

Salicylaldehyde and its derivatives are an important class of compounds which can be used in a variety of studies such as organic synthesis, catalysis, drug design, the spice industry and the life sciences (Dong et al., 2007a; Dong & Duan, 2008). In the past few decades, continuing attention has been drawn to derivatives of the salicylaldehyde and their metal complexes for the investigation of luminescent properties which could be finely tuned by different substituent groups bonded to the phenolic ring (Dong et al., 2008). In this paper, we report synthesis and X-ray structure of 6,6'-diethoxy-2,2'-[(1,3-propylene)dioxybis(nitrilomethylidyne)]diphenol, (I).

As shown in Fig. 1, the single-crystal structure of (I) is built up by only the C21H26N2O6 molecules, in which all bond lengths are in normal ranges. Two benzene rings (C4—C9) of molecule are perpendicular each other with a dihedral angle of 89.53 (3)°. There is a crystallographic twofold rotation axis passing through the middle point of the C—C—C unit. The molecule adopts a trans conguration in which two phenoldoxime moieties adopts an extended form, where the oxime and phenolic alcohols lie in trans positions relative to the C2 atom in the N—-O—CH2—CH2—CH2—O—N linkage. A pair of intramolecular O2—H2···N1 hydrogen bonds generate two six-membered rings, producing two S(6) ring motifs (Table 1, Fig. 1) (Bernstein et al., 1995). Intermolecular C11—H11C···O1 hydrogen bonds (Desiraju et al., 1996) link neighbouring molecules into a supermolecular structure (Fig. 2). Moreover, the packing diagram of the title compound shows a infinete netwok structure viewed along the b-axes (Fig. 3).

Related literature top

For background to salen-type bisoxime compounds, see: Dong et al. (2007a,b; Dong & Duan, 2008). For the synthesis, see: Dong et al. (2008, 2009). For background to hydrogen bonding, see: Desiraju (1996). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

6,6'-Diethoxy-2,2'-[(1,3-propylene)dioxybis(nitrilomethylidyne)]diphenol was synthesized according to an analogous method reported earlier (Dong et al., 2007b; Dong et al., 2009). To an ethanol solution (4 ml) of 3-ethoxysalicylaldehyde(167.4 mg, 1.00 mmol) was added an ethanol solution (2 ml) of 1,3-bis(aminooxy)propylene (60.07 mg, 0.50 mmol). The mixed solution was stirred at 338 K for 5 h. The precipitate was filtered, and washed successively with ethanol and ether, respectively. The product was dried under vacuum to yield 160.3 mg of (I). Yield, 76.6%. m.p. 462.5-463.5 K. Anal. Calcd. for C21H26N2O6: C, 62.67; H, 6.51; N, 6.96. Found: C, 62.61; H, 6.40; N, 7.01.

Colorless needle-like single crystals suitable for X-ray diffraction studies were obtained after one weeks by slow evaporation from methanol solution of the title compound.

Refinement top

H atoms were placed in calculated positions and non-H atoms were refined anisotropically. The remaining H atoms were treated as riding atoms with distances C—H = 0.96 Å (CH3), 0.97 Å (CH2), 0.93 Å (CH), 0.82 Å (OH), and Uiso(H) = 1.20 Ueq(C), 1.50 Ueq(O). In the absence of significant anomalous scatterers, Friedel pairs were merged before final refinement.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 molecule structure of the title compound with the atom numbering scheme [Symmetry codes for A atoms: -x+1/2, -y+1/2, z]. Displacement ellipsoids for non-hydrogen atoms are drawn at the 30% probability level.
[Figure 2] Fig. 2. Digram showing the intramolecular O—H···N and intermolecular C—H···O hydrogen bonding interactions. Hydrogen atoms not involved have been deleated for clarity.
[Figure 3] Fig. 3. The packing digram of the title compound viewed along the b-axis.
6,6'-Diethoxy-2,2'-[propane-1,3-diyldioxybis(nitrilomethylidyne)]diphenol top
Crystal data top
C21H26N2O6F(000) = 1712
Mr = 402.44Dx = 1.302 Mg m−3
Orthorhombic, Fdd2Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2dCell parameters from 1648 reflections
a = 25.292 (2) Åθ = 2.9–25.3°
b = 34.412 (3) ŵ = 0.10 mm−1
c = 4.7176 (5) ÅT = 298 K
V = 4105.9 (7) Å3Needle-like, colorless
Z = 80.45 × 0.18 × 0.17 mm
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer		1031 independent reflections
Radiation source: fine-focus sealed tube817 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.048
phi and ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −30→29
Tmin = 0.958, Tmax = 0.984k = −30→40
5348 measured reflectionsl = −5→5
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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.051P)2]
where P = (Fo2 + 2Fc2)/3
1031 reflections(Δ/σ)max < 0.001
133 parametersΔρmax = 0.16 e Å−3
1 restraintΔρmin = −0.14 e Å−3
Crystal data top
C21H26N2O6V = 4105.9 (7) Å3
Mr = 402.44Z = 8
Orthorhombic, Fdd2Mo Kα radiation
a = 25.292 (2) ŵ = 0.10 mm−1
b = 34.412 (3) ÅT = 298 K
c = 4.7176 (5) Å0.45 × 0.18 × 0.17 mm
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer		1031 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		817 reflections with I > 2σ(I)
Tmin = 0.958, Tmax = 0.984Rint = 0.048
5348 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0371 restraint
wR(F2) = 0.090H-atom parameters constrained
S = 1.04Δρmax = 0.16 e Å−3
1031 reflectionsΔρmin = −0.14 e Å−3
133 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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*/UeqOcc. (<1)
N10.23158 (9)0.17094 (6)0.6113 (5)0.0506 (6)
O10.21889 (7)0.20179 (5)0.4290 (5)0.0556 (5)
O20.28824 (6)0.11584 (5)0.8533 (5)0.0577 (6)
H20.28260.13340.73990.087*
O30.29360 (7)0.05913 (6)1.2148 (5)0.0613 (6)
C10.26566 (10)0.21504 (7)0.2881 (7)0.0518 (7)
H1A0.27960.19480.16600.062*
H1B0.29260.22200.42550.062*
C20.25000.25000.1155 (10)0.0525 (10)
H2A0.27940.2571−0.00590.063*0.50
H2B0.22060.2429−0.00590.063*0.50
C30.19084 (11)0.15810 (7)0.7412 (6)0.0485 (7)
H30.15800.16920.70500.058*
C40.19489 (10)0.12638 (7)0.9451 (6)0.0445 (7)
C50.24271 (10)0.10703 (7)0.9928 (6)0.0437 (7)
C60.24500 (10)0.07660 (7)1.1909 (6)0.0456 (7)
C70.20034 (10)0.06695 (8)1.3422 (7)0.0532 (7)
H70.20210.04741.47820.064*
C80.15281 (11)0.08595 (8)1.2947 (7)0.0555 (8)
H80.12280.07881.39600.067*
C90.15006 (10)0.11522 (8)1.0988 (7)0.0514 (7)
H90.11810.12781.06740.062*
C100.29937 (10)0.02900 (8)1.4204 (7)0.0603 (9)
H10A0.27390.00851.38670.072*
H10B0.29390.03921.61000.072*
C110.35463 (10)0.01383 (9)1.3886 (11)0.0812 (12)
H11A0.36090.00721.19380.122*
H11B0.3590−0.00881.50480.122*
H11C0.37930.03351.44670.122*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0629 (14)0.0383 (12)0.0506 (15)−0.0003 (10)−0.0073 (13)0.0030 (13)
O10.0583 (11)0.0451 (10)0.0635 (14)−0.0006 (8)−0.0057 (10)0.0129 (10)
O20.0507 (11)0.0625 (12)0.0599 (14)0.0013 (8)0.0034 (10)0.0155 (12)
O30.0545 (10)0.0622 (12)0.0670 (15)0.0057 (8)−0.0027 (11)0.0205 (12)
C10.0586 (17)0.0438 (15)0.0529 (18)−0.0020 (12)−0.0020 (15)−0.0035 (15)
C20.060 (2)0.051 (2)0.046 (2)−0.0072 (17)0.0000.000
C30.0545 (16)0.0413 (15)0.0499 (18)0.0027 (12)−0.0071 (15)−0.0030 (15)
C40.0535 (15)0.0354 (14)0.0444 (17)−0.0013 (11)−0.0055 (14)−0.0053 (13)
C50.0455 (14)0.0428 (14)0.0427 (17)−0.0046 (11)−0.0020 (13)−0.0031 (14)
C60.0487 (14)0.0417 (14)0.0465 (17)−0.0014 (11)−0.0037 (13)−0.0011 (14)
C70.0617 (17)0.0478 (15)0.0500 (18)−0.0069 (12)0.0014 (16)0.0036 (15)
C80.0526 (15)0.0552 (16)0.059 (2)−0.0083 (13)0.0075 (15)0.0010 (17)
C90.0460 (15)0.0499 (15)0.0582 (19)0.0011 (11)−0.0019 (14)−0.0040 (16)
C100.0656 (19)0.0518 (17)0.063 (2)−0.0042 (12)−0.0133 (16)0.0170 (17)
C110.0635 (19)0.070 (2)0.110 (3)0.0007 (15)−0.017 (2)0.032 (3)
Geometric parameters (Å, º) top
N1—C31.278 (3)C4—C51.399 (3)
N1—O11.403 (3)C4—C91.400 (4)
O1—C11.431 (3)C5—C61.405 (4)
O2—C51.361 (3)C6—C71.377 (4)
O2—H20.8200C7—C81.387 (4)
O3—C61.373 (3)C7—H70.9300
O3—C101.427 (3)C8—C91.369 (4)
C1—C21.506 (4)C8—H80.9300
C1—H1A0.9700C9—H90.9300
C1—H1B0.9700C10—C111.500 (4)
C2—C1i1.506 (4)C10—H10A0.9700
C2—H2A0.9700C10—H10B0.9700
C2—H2B0.9700C11—H11A0.9600
C3—C41.459 (4)C11—H11B0.9600
C3—H30.9300C11—H11C0.9600
C3—N1—O1111.8 (2)O3—C6—C7125.9 (2)
N1—O1—C1109.68 (18)O3—C6—C5114.7 (2)
C5—O2—H2109.5C7—C6—C5119.4 (2)
C6—O3—C10117.7 (2)C6—C7—C8120.9 (3)
O1—C1—C2106.76 (19)C6—C7—H7119.5
O1—C1—H1A110.4C8—C7—H7119.5
C2—C1—H1A110.4C9—C8—C7120.0 (3)
O1—C1—H1B110.4C9—C8—H8120.0
C2—C1—H1B110.4C7—C8—H8120.0
H1A—C1—H1B108.6C8—C9—C4120.7 (2)
C1i—C2—C1114.5 (4)C8—C9—H9119.6
C1i—C2—H2A108.6C4—C9—H9119.6
C1—C2—H2A108.6O3—C10—C11106.3 (3)
C1i—C2—H2B108.6O3—C10—H10A110.5
C1—C2—H2B108.6C11—C10—H10A110.5
H2A—C2—H2B107.6O3—C10—H10B110.5
N1—C3—C4121.2 (2)C11—C10—H10B110.5
N1—C3—H3119.4H10A—C10—H10B108.7
C4—C3—H3119.4C10—C11—H11A109.5
C5—C4—C9119.1 (3)C10—C11—H11B109.5
C5—C4—C3121.5 (2)H11A—C11—H11B109.5
C9—C4—C3119.3 (2)C10—C11—H11C109.5
O2—C5—C4123.2 (2)H11A—C11—H11C109.5
O2—C5—C6116.9 (2)H11B—C11—H11C109.5
C4—C5—C6119.8 (2)
C3—N1—O1—C1−179.8 (2)O2—C5—C6—O3−0.9 (3)
N1—O1—C1—C2−175.5 (2)C4—C5—C6—O3178.4 (2)
O1—C1—C2—C1i67.48 (19)O2—C5—C6—C7178.7 (2)
O1—N1—C3—C4−179.0 (2)C4—C5—C6—C7−1.9 (4)
N1—C3—C4—C5−4.3 (4)O3—C6—C7—C8−178.2 (3)
N1—C3—C4—C9175.1 (3)C5—C6—C7—C82.2 (4)
C9—C4—C5—O2179.9 (3)C6—C7—C8—C9−1.2 (4)
C3—C4—C5—O2−0.7 (4)C7—C8—C9—C4−0.1 (4)
C9—C4—C5—C60.6 (4)C5—C4—C9—C80.4 (4)
C3—C4—C5—C6−180.0 (2)C3—C4—C9—C8−179.0 (3)
C10—O3—C6—C7−2.1 (4)C6—O3—C10—C11176.8 (3)
C10—O3—C6—C5177.5 (2)
Symmetry code: (i) −x+1/2, −y+1/2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···N10.821.922.636 (2)145
C11—H11C···O1ii0.962.573.410 (3)146
Symmetry code: (ii) x+1/4, −y+1/4, z+5/4.

Experimental details

Crystal data
Chemical formulaC21H26N2O6
Mr402.44
Crystal system, space groupOrthorhombic, Fdd2
Temperature (K)298
a, b, c (Å)25.292 (2), 34.412 (3), 4.7176 (5)
V (Å3)4105.9 (7)
Z8
Radiation typeMo Kα
µ (mm−1)0.10
Crystal size (mm)0.45 × 0.18 × 0.17
Data collection
DiffractometerBruker SMART 1000 CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.958, 0.984
No. of measured, independent and
observed [I > 2σ(I)] reflections		5348, 1031, 817
Rint0.048
(sin θ/λ)max (Å−1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.090, 1.04
No. of reflections1031
No. of parameters133
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.16, −0.14

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···N10.821.922.636 (2)145.0
C11—H11C···O1i0.962.573.410 (3)146.0
Symmetry code: (i) x+1/4, −y+1/4, z+5/4.
 

Acknowledgements

This work was supported by the Foundation of the Education Department of Gansu Province (0904–11) and the `Jing Lan' Talent Engineering Funds of Lanzhou Jiaotong University, which are gratefully acknowledged.

References

First citationBernstein, J., Davis, R. E., Shimoni, L. & Chang, N. L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.  CrossRef CAS Web of Science Google Scholar
 First citationDesiraju, G. R. (1996). Acc. Chem. Res. 29, 441–449.  CrossRef CAS PubMed Web of Science Google Scholar
 First citationDong, W.-K. & Duan, J.-G. (2008). J. Coord. Chem. 61, 781–788.  Web of Science CSD CrossRef CAS Google Scholar
 First citationDong, W.-K., Duan, J.-G. & Liu, G.-L. (2007a). Transition Met. Chem. 32, 702–705.  Web of Science CSD CrossRef CAS Google Scholar
 First citationDong, W.-K., Feng, J.-H. & Yang, X.-Q. (2007b). Synth. React. Inorg. Met. Org. Nano-Chem. 37, 61–65.  Web of Science CSD CrossRef CAS Google Scholar
 First citationDong, W.-K., He, X.-N., Yan, H.-B., Lv, Z.-W., Chen, X., Zhao, C.-Y. & Tang, X.-L. (2009). Polyhedron, 28, 1419–1428.  Web of Science CSD CrossRef CAS Google Scholar
 First citationDong, W.-K., Zhang, Y.-P., Zhao, C.-Y., Tang, X.-L., Lv, Z.-W. & Zou, Z. (2008). Chin. J. Chem. 21, 1821–1825.  Web of Science CSD CrossRef Google Scholar
 First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSiemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.  Google Scholar

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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 3| March 2010| Page o512
doi:10.1107/S1600536810003430
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