• No results found

3 [4 (5 Formyl 2 meth­oxy­phen­­oxy)but­­oxy] 4 meth­oxy­benzaldehyde

N/A
N/A
Protected

Academic year: 2020

Share "3 [4 (5 Formyl 2 meth­oxy­phen­­oxy)but­­oxy] 4 meth­oxy­benzaldehyde"

Copied!
6
0
0

Loading.... (view fulltext now)

Full text

(1)

organic papers

Acta Cryst.(2005). E61, o4049–o4050 doi:10.1107/S1600536805036135 Han and Zhen C

20H22O6

o4049

Acta Crystallographica Section E Structure Reports Online

ISSN 1600-5368

3-[4-(5-Formyl-2-methoxyphenoxy)butoxy]-4-methoxybenzaldehyde

Jian-Rong Han* and Xiao-Li Zhen

College of Sciences, Hebei University of Science & Technology, Shijiazhuang 050018, People’s Republic of China

Correspondence e-mail: han_jianrong@163.com

Key indicators

Single-crystal X-ray study T= 294 K

Mean(C–C) = 0.004 A˚ Rfactor = 0.049 wRfactor = 0.131

Data-to-parameter ratio = 15.9

For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.

#2005 International Union of Crystallography Printed in Great Britain – all rights reserved

The molecule of the title compound, C20H22O6, lies on

crystallographic center of symmetry. The isovanillin group makes a dihedral angle of 2.8 (5)with the four C atoms of the

central chain. A weak intermolecular C—H O hydrogen

bond links molecules into extended one-dimensional chains.

Comment

Since the early work on macrocyclic crown ethers was carried out by Pedersen (1967), considerable effort has been devoted to the study of these species (Kimet al., 1999). Crown ethers are capable of forming stable and selective complexes with metal cations, halide anions and small organic molecules. We are interested in the molecular and ionic recognition of these crown ethers. As part of this study, we report the synthesis and structure of the title compound, (I), used as a precursor in their preparation.

In (I) (Fig. 1), a crystallographic center of symmetry is located at the mid-point of the central C—C bond. The bond lengths and angles are as expected. The isovanillin group (C1– C7/O1/O2/O3) is essentially planar, with an r.m.s. deviation for the fitted atoms of 0.0261 A˚ . The torsion angle of 176.8 (2)for

C6—C1—O1—C9, in conjunction with the value of 2.8 (5)for

the dihedral angle between the central chain of C atoms and the isovanillin group, confirm the nearly planar conformation of the molecule. The geometry is similar to that in 4-[6-(4- formyl-2-methoxyphenoxy)hexyloxy]-3-methoxybenzalde-hyde (Diaoet al., 2005), in which the dihedral angle between the central C-atom chain and the atoms of the isovanillin group is 3.0 (3)

A weak intermolecular C—H O hydrogen bond (Table 1)

links molecules into extended one-dimensional chains (Fig. 2).

Experimental

To a solution of 3-hydroxy-4-methoxybenzaldehyde (15.2 g, 100 mmol) and potassium carbonate (13.8 g, 100 mmol) in aceto-nitrile (500 ml), 1,4-dibromobutane (10.8 g, 50 mmol) was added dropwise over a period of 30 min, and the mixture refluxed for 24 h under nitrogen. The solvent was removed and the resultant mixture poured into ice-water (500 ml). The white precipitate was then

(2)

isolated and recrystallized from ethanol to give the pure compound in 51% yield. Colorless single crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of an acetonitrile solution.

Crystal data

C20H22O6

Mr= 358.38 Monoclinic,P21=n

a= 7.828 (2) A˚

b= 7.261 (2) A˚

c= 16.445 (4) A˚

= 94.499 (5) V= 931.9 (4) A˚3

Z= 2

Dx= 1.277 Mg m3 MoKradiation Cell parameters from 1180

reflections

= 3.0–24.3

= 0.09 mm1

T= 294 (2) K Block, colorless 0.220.200.14 mm

Data collection

Bruker SMART-CCD area-detector diffractometer

’and!scans

Absorption correction: multi-scan (SADABS; Sheldrick, 1996)

Tmin= 0.972,Tmax= 0.987

5085 measured reflections

1907 independent reflections 1109 reflections withI> 2(I)

Rint= 0.039 max= 26.4

h=9!9

k=8!9

l=20!12

Refinement

Refinement onF2

R[F2> 2(F2)] = 0.049

wR(F2) = 0.131

S= 1.14 1907 reflections 120 parameters

H-atom parameters constrained

w= 1/[2(F

o2) + (0.0515P)2

+ 0.0565P]

whereP= (Fo2+ 2Fc2)/3

(/)max= 0.005 max= 0.39 e A˚

3 min=0.24 e A˚

3

Table 1

Hydrogen-bond geometry (A˚ ,).

D—H A D—H H A D A D—H A

C8—H8B O1i

0.96 2.57 3.512 (4) 167

Symmetry code: (i)x;yþ2;zþ2.

H atoms were included in calculated positions and refined using a riding-model approximation, with C—H bond lengths and isotropicU parameters as follows: 0.93 A˚ andUiso(H) = 1.2Ueq(C) for aromatic CH; 0.97 A˚ andUiso(H) = 1.2Ueq(C) for methylene CH2; 0.96 A˚ and Uiso(H) = 1.5Ueq(C) for methyl CH3.

Data collection:SMART(Bruker, 1999); cell refinement:SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure:SHELXS97(Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL(Sheldrick, 1997b); software used to prepare material for publication:SHELXTL.

References

Bruker (1999).SMART(Version 5.0) andSAINT(Version 4.0) for Windows NT. Bruker AXS Inc., Madison, Wisconsin, USA.

Diao, C.-H., Guo, M.-J., Yu, M., Chen, X. & Jing, Z.-L. (2005).Acta Cryst.E61, o3670–o3671.

Kim, J., Shamsipur, M., Huang, S. Z., Huang, R. H. & Dye, J. L. (1999).J. Phys. Chem. A,103, 5615–5620.

Pedersen, C. J. (1967).J. Am. Chem. Soc.89, 7017–7036.

Sheldrick, G. M. (1996).SADABS. University of Go¨ttingen, Germany. Sheldrick, G. M. (1997a). SHELXS97 and SHELXL97. University of

Go¨ttingen, Germany.

Sheldrick, G. M. (1997b).SHELXTL. Version 5.10 for Windows NT. Bruker AXS Inc., Madison, Wisconsin, USA.

Figure 2

[image:2.610.314.565.70.223.2] [image:2.610.313.565.284.481.2]

Partial packing diagram, showing hydrogen-bonding interactions as dashed lines.

Figure 1

(3)

supporting information

sup-1 Acta Cryst. (2005). E61, o4049–o4050

supporting information

Acta Cryst. (2005). E61, o4049–o4050 [https://doi.org/10.1107/S1600536805036135]

3-[4-(5-Formyl-2-methoxyphenoxy)butoxy]-4-methoxybenzaldehyde

Jian-Rong Han and Xiao-Li Zhen

3-[4-(5-Formyl-2-methoxyphenoxy)butoxy]-4-methoxybenzaldehyde

Crystal data

C20H22O6 Mr = 358.38

Monoclinic, P21/n Hall symbol: -P 2yn a = 7.828 (2) Å b = 7.261 (2) Å c = 16.445 (4) Å β = 94.499 (5)° V = 931.9 (4) Å3 Z = 2

F(000) = 380 Dx = 1.277 Mg m−3

Mo Kα radiation, λ = 0.71073 Å Cell parameters from 1180 reflections θ = 3.0–24.3°

µ = 0.09 mm−1 T = 294 K Block, colorless 0.22 × 0.20 × 0.14 mm

Data collection

Bruker SMART-CCD area-detector diffractometer

Radiation source: fine-focus sealed tube Graphite monochromator

φ and ω scans

Absorption correction: multi-scan (SADABS; Sheldrick, 1996) Tmin = 0.972, Tmax = 0.987

5085 measured reflections 1907 independent reflections 1109 reflections with I > 2σ(I) Rint = 0.039

θmax = 26.4°, θmin = 2.5° h = −9→9

k = −8→9 l = −20→12

Refinement

Refinement on F2 Least-squares matrix: full R[F2 > 2σ(F2)] = 0.049 wR(F2) = 0.131 S = 1.14 1907 reflections 120 parameters 6 restraints

Primary atom site location: structure-invariant direct methods

Secondary atom site location: difference Fourier map

Hydrogen site location: inferred from neighbouring sites

H-atom parameters constrained w = 1/[σ2(F

o2) + (0.0515P)2 + 0.0565P] where P = (Fo2 + 2Fc2)/3

(Δ/σ)max = 0.005 Δρmax = 0.39 e Å−3 Δρmin = −0.24 e Å−3

Special details

(4)

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 > 2σ(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)

x y z Uiso*/Ueq

O1 0.3564 (2) 1.1337 (3) 0.93699 (12) 0.0468 (6)

O2 0.1157 (3) 0.8943 (3) 0.93578 (14) 0.0609 (7)

O3 0.7434 (4) 0.9003 (5) 0.7134 (2) 0.1058 (11)

C1 0.3709 (4) 0.9911 (4) 0.88433 (16) 0.0381 (7)

C2 0.4974 (4) 0.9701 (4) 0.83234 (17) 0.0443 (8)

H2 0.5848 1.0568 0.8320 0.053*

C3 0.4958 (4) 0.8187 (5) 0.77955 (19) 0.0511 (9)

C4 0.3672 (5) 0.6902 (5) 0.7810 (2) 0.0594 (10)

H4 0.3675 0.5883 0.7467 0.071*

C5 0.2383 (4) 0.7103 (5) 0.8323 (2) 0.0570 (10)

H5 0.1515 0.6229 0.8322 0.068*

C6 0.2373 (4) 0.8594 (4) 0.88392 (18) 0.0444 (8)

C7 0.6247 (5) 0.7975 (6) 0.7213 (2) 0.0749 (12)

H7 0.6149 0.6955 0.6871 0.090*

C8 −0.0297 (4) 0.7735 (5) 0.9342 (3) 0.0820 (13)

H8A −0.0870 0.7728 0.8804 0.123*

H8B −0.1072 0.8158 0.9725 0.123*

H8C 0.0080 0.6511 0.9485 0.123*

C9 0.4826 (4) 1.2768 (4) 0.93739 (17) 0.0419 (8)

H9A 0.4840 1.3305 0.8834 0.050*

H9B 0.5954 1.2272 0.9531 0.050*

C10 0.4365 (4) 1.4205 (4) 0.99753 (17) 0.0401 (8)

H10A 0.4338 1.3646 1.0510 0.048*

H10B 0.3228 1.4675 0.9816 0.048*

Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23

O1 0.0509 (13) 0.0364 (13) 0.0548 (13) −0.0134 (10) 0.0154 (10) −0.0120 (10) O2 0.0524 (14) 0.0518 (15) 0.0803 (17) −0.0198 (11) 0.0159 (12) −0.0125 (12) O3 0.1102 (15) 0.1046 (16) 0.1098 (15) −0.0033 (12) 0.0536 (12) −0.0201 (12) C1 0.0443 (17) 0.0305 (17) 0.0392 (17) −0.0022 (13) −0.0002 (14) −0.0037 (13) C2 0.0497 (18) 0.0366 (19) 0.0465 (18) −0.0029 (15) 0.0023 (15) −0.0012 (15)

C3 0.063 (2) 0.043 (2) 0.0461 (19) 0.0090 (17) 0.0006 (16) −0.0065 (15)

C4 0.077 (2) 0.043 (2) 0.056 (2) −0.0012 (19) −0.0084 (19) −0.0181 (16)

C5 0.060 (2) 0.043 (2) 0.066 (2) −0.0107 (17) −0.0081 (19) −0.0102 (18)

C6 0.0456 (18) 0.0371 (19) 0.0495 (19) −0.0047 (15) −0.0024 (15) −0.0010 (14)

C7 0.090 (3) 0.066 (3) 0.071 (3) 0.006 (2) 0.021 (2) −0.018 (2)

C8 0.058 (2) 0.068 (3) 0.122 (3) −0.031 (2) 0.021 (2) −0.018 (3)

(5)

supporting information

sup-3 Acta Cryst. (2005). E61, o4049–o4050

C10 0.0430 (16) 0.0338 (17) 0.0444 (17) −0.0069 (13) 0.0084 (14) −0.0017 (13)

Geometric parameters (Å, º)

O1—C1 1.360 (3) C5—C6 1.376 (4)

O1—C9 1.434 (3) C5—H5 0.9300

O2—C6 1.351 (3) C7—H7 0.9300

O2—C8 1.436 (4) C8—H8A 0.9600

O3—C7 1.207 (4) C8—H8B 0.9600

C1—C2 1.366 (4) C8—H8C 0.9600

C1—C6 1.417 (4) C9—C10 1.501 (4)

C2—C3 1.400 (4) C9—H9A 0.9700

C2—H2 0.9300 C9—H9B 0.9700

C3—C4 1.374 (4) C10—C10i 1.522 (5)

C3—C7 1.452 (5) C10—H10A 0.9700

C4—C5 1.374 (5) C10—H10B 0.9700

C4—H4 0.9300

C1—O1—C9 117.6 (2) O3—C7—H7 117.1

C6—O2—C8 118.0 (3) C3—C7—H7 117.1

O1—C1—C2 125.7 (3) O2—C8—H8A 109.5

O1—C1—C6 114.7 (3) O2—C8—H8B 109.5

C2—C1—C6 119.5 (3) H8A—C8—H8B 109.5

C1—C2—C3 120.3 (3) O2—C8—H8C 109.5

C1—C2—H2 119.9 H8A—C8—H8C 109.5

C3—C2—H2 119.9 H8B—C8—H8C 109.5

C4—C3—C2 119.6 (3) O1—C9—C10 107.8 (2)

C4—C3—C7 119.1 (3) O1—C9—H9A 110.1

C2—C3—C7 121.3 (3) C10—C9—H9A 110.1

C5—C4—C3 120.8 (3) O1—C9—H9B 110.1

C5—C4—H4 119.6 C10—C9—H9B 110.1

C3—C4—H4 119.6 H9A—C9—H9B 108.5

C4—C5—C6 120.2 (3) C9—C10—C10i 111.9 (3)

C4—C5—H5 119.9 C9—C10—H10A 109.2

C6—C5—H5 119.9 C10i—C10—H10A 109.2

O2—C6—C5 125.1 (3) C9—C10—H10B 109.2

O2—C6—C1 115.3 (3) C10i—C10—H10B 109.2

C5—C6—C1 119.6 (3) H10A—C10—H10B 107.9

O3—C7—C3 125.9 (4)

C9—O1—C1—C2 1.2 (4) C4—C5—C6—O2 178.8 (3)

C9—O1—C1—C6 −176.8 (2) C4—C5—C6—C1 −0.6 (5)

O1—C1—C2—C3 −178.5 (3) O1—C1—C6—O2 −0.1 (4)

C6—C1—C2—C3 −0.6 (4) C2—C1—C6—O2 −178.3 (3)

C1—C2—C3—C4 −0.7 (5) O1—C1—C6—C5 179.4 (3)

C1—C2—C3—C7 177.4 (3) C2—C1—C6—C5 1.2 (4)

C2—C3—C4—C5 1.3 (5) C4—C3—C7—O3 179.6 (4)

(6)

C3—C4—C5—C6 −0.7 (5) C1—O1—C9—C10 178.0 (2)

C8—O2—C6—C5 −3.9 (5) O1—C9—C10—C10i 180.0 (3)

C8—O2—C6—C1 175.6 (3)

Symmetry code: (i) −x+1, −y+3, −z+2.

Hydrogen-bond geometry (Å, º)

D—H···A D—H H···A D···A D—H···A

C8—H8B···O1ii 0.96 2.57 3.512 (4) 167

Figure

Figure 1

References

Related documents

In this study, we identified 9 protein markers for predicting time to recurrence using the protein expression data on 222 TCGA pri- marily high-grade serous ovarian cancers

For the purpose of analyzing the impurities in the water samples coming from different roofs, four building within the KCAET campus viz location 1(library -

To overcome the problems and weakness, this project need to do some research and studying to develop better technology. There are list of the objectives to be conduct

The above block diagram shows the SPV fed to Dc/Dc Converter for different dc applications, To analysis the performance of dc-dc converters(Buck, Boost,

22 subjects showing low or undetectable activities of BAT were randomly divided into 2 groups: one was exposed to cold at 17°C for 2 hours every day for 6 weeks (cold group; n

Foxo deletion on osteoblast differentiation in both bone marrow and calvaria cells suggests that the increases in ALP activity and mineralization observed in the bone

Histologically, the lesion is composed of fibrous connective tissue trabeculae (top quarter of image) and adipose connective tissue (bottom three quarters of image); within

• Data shows credit using and rationing of risk averts, risk neutrals and risk lovers respectively. As to risk averts, the credit is mainly used to pay children’s tuition, medical