1,5-Bis(2-formyl­phen­oxy)-3-oxapenta­ne

Dionysio, N.C.F.; Bordinhão, J.; Visentin, L. do C.; Ronconi, C.M.

doi:10.1107/S1600536808002948

organic compounds

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ISSN: 2056-9890

Volume 64| Part 3| March 2008| Page o546

doi:10.1107/S1600536808002948

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1,5-Bis(2-formylphenoxy)-3-oxapentane

Nívea C. F. Dionysio,^a Jairo Bordinhão,^a Lorenzo do Canto Visentin ^a and Célia Machado Ronconi ^a ^*

^aInstituto de Química, Universidade Federal do Rio de Janeiro, Caixa Postal 68563, 21949-900 Rio de Janeiro, RJ, Brazil
^*Correspondence e-mail: ronconi@iq.ufrj.br

(Received 29 November 2007; accepted 25 January 2008; online 6 February 2008)

In the title molecule, C₁₈H₁₈O₅, the two aromatic rings are connected by a flexible 3-oxapentane chain. The molecule has a crystallographic twofold rotation axis (C₂) passing through the central O atom. An intramolecular C—H⋯O hydrogen bond is observed in the solid state.

Related literature

For related literature, see: Biernat et al. (1992 ); Qi et al. (2005 ); Jeffrey & Saenger (1991 ); Spek (2003 ).

Experimental

Crystal data

C₁₈H₁₈O₅
M_r = 314.32
Orthorhombic, F d d 2
a = 27.613 (6) Å
b = 26.404 (5) Å
c = 4.4313 (9) Å
V = 3230.8 (11) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 295 (2) K
0.25 × 0.08 × 0.05 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: none
4449 measured reflections
1043 independent reflections
480 reflections with I > 2σ(I)
R_int = 0.134

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.097
S = 0.99
1043 reflections
105 parameters
H-atom parameters constrained
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯O2	0.93	2.42	2.764 (5)	102

Data collection: COLLECT (Nonius, 1998 ); cell refinement: PHICHI (Duisenberg et al., 2000 ); data reduction: EVAL-14 (CCD) (Duisenberg et al., 2003 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808002948/si2065sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808002948/si2065Isup2.hkl

checkCIF report

Comment top

The title molecule is generated by a symmetry operation according to the space group Fdd2. The symmetry operator (0, 1/2, z) applied to the equivalent atoms is a twofold rotation axis passing through the central atom O1 (Fig. 1). Bond lengths and angles are in the ranges reported for analogous structures (Biernat et al., 1992; Qi et al., 2005). The distances involving the C atoms in the central moiety are 1.496 (5) Å for C1—C2, 1.429 (4) Å for C1—O1, and 1.436 (4) Å for C2—O2.

The intramolecular C9—H9···O2 contact observed in the solid state (Fig. 1) is classificated as a non classical hydrogen bond (Jeffrey & Saenger, 1991). This secondary interaction does not affect the torsion angles in the 3-oxapentane chain. The torsion angle for the O2/C2/C1/O1 moiety is -69.3 (3)° and proves the flexibility of the 3-oxapentane chain. The hydrogen bonding geometry of the intramolecular contacts (Jeffrey & Saenger, 1991) with atom O2 as acceptor was calculated with PLATON (Spek, 2003): distances H9···O2 and C9···O2 are 2.42 and 2.764 (5) Å, respectively, and the angle at H9 is 102°.

Related literature top

For related literature, see: Biernat et al. (1992); Qi et al. (2005); Jeffrey & Saenger (1991); Spek (2003).

Experimental top

A mixture of 2[2-(2-p-tolylsulfonyloxy)ethoxy]ethanol (1 g, 8.19 mmol), salicylic aldehyde (0.87 g, 2.10 mmol), and K₂CO₃ (0.47 g, 3.40 mmol) in dry MeCN (20 ml) was heated for 12 h under reflux. After the reaction mixture had cooled down to room temperature, it was filtered and the solvent removed under vacuum. The residue was purified by column chromatography (SiO₂, Hexane:EtOAc 1:1) to give the desired product (0.55 g, 83%) as a yellow solid. A single-crystal was isolated after slow evaporation of the crystallization solvent (THF).

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: PHICHI (Duisenberg et al., 2000); data reduction: EVAL14 (CCD) (Duisenberg et al., 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. ORTEP projection of the title molecule. Symmetry equivalent atoms are generated by the symmetry code [-x, 1 - y, z]. Intramolecular bonds are indicated by dashed lines. Thermal ellipsoids are shown at the 50% probability level.

1,5-Bis(2-formylphenoxy)-3-oxapentane top

Crystal data top

C₁₈H₁₈O₅	F(000) = 1328
M_r = 314.32	D_x = 1.292 Mg m⁻³
Orthorhombic, Fdd2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2d	Cell parameters from 50 reflections
a = 27.613 (6) Å	θ = 1–27.5°
b = 26.404 (5) Å	µ = 0.09 mm⁻¹
c = 4.4313 (9) Å	T = 295 K
V = 3230.8 (11) Å³	Plate, yellow
Z = 8	0.25 × 0.08 × 0.05 mm

Data collection top

Nonius KappaCCD diffractometer	480 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.134
Graphite monochromator	θ_max = 27.5°, θ_min = 3.1°
ϕ and ω scans with κ offsets	h = −34→35
4449 measured reflections	k = −34→34
1043 independent reflections	l = −5→5

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.097	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0377P)²] where P = (F_o² + 2F_c²)/3
1043 reflections	(Δ/σ)_max < 0.001
105 parameters	Δρ_max = 0.12 e Å⁻³
0 restraints	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₁₈H₁₈O₅	V = 3230.8 (11) Å³
M_r = 314.32	Z = 8
Orthorhombic, Fdd2	Mo Kα radiation
a = 27.613 (6) Å	µ = 0.09 mm⁻¹
b = 26.404 (5) Å	T = 295 K
c = 4.4313 (9) Å	0.25 × 0.08 × 0.05 mm

Data collection top

Nonius KappaCCD diffractometer	480 reflections with I > 2σ(I)
4449 measured reflections	R_int = 0.134
1043 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.097	H-atom parameters constrained
S = 0.99	Δρ_max = 0.12 e Å⁻³
1043 reflections	Δρ_min = −0.14 e Å⁻³
105 parameters

Special details top

Experimental. The transformation of the unit cell axes and hkl intensity data were performed by using the matrix (00–1, 010, 100) in order to solve and refine the structure in the standard setting for space group Fdd2.

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
C1	0.03242 (14)	0.47183 (13)	1.1699 (9)	0.0683 (12)
H1A	0.0138	0.4508	1.3069	0.082*
H1B	0.0515	0.4951	1.2902	0.082*
C2	0.06560 (13)	0.43903 (12)	0.9883 (9)	0.0607 (10)
H2A	0.0831	0.4162	1.1207	0.073*
H2B	0.0469	0.4188	0.8472	0.073*
C3	0.13695 (13)	0.44746 (12)	0.6829 (8)	0.0495 (9)
C4	0.14652 (13)	0.39549 (12)	0.6935 (9)	0.0622 (11)
H4	0.1263	0.3740	0.8015	0.075*
C5	0.18651 (15)	0.37623 (15)	0.5414 (11)	0.0773 (13)
H5	0.1930	0.3417	0.5519	0.093*
C6	0.21687 (15)	0.40706 (15)	0.3753 (10)	0.0731 (13)
H6	0.2433	0.3935	0.2739	0.088*
C7	0.20743 (14)	0.45820 (15)	0.3617 (9)	0.0677 (13)
H7	0.2276	0.4791	0.2491	0.081*
C8	0.16770 (12)	0.47928 (12)	0.5159 (10)	0.0523 (10)
C9	0.15870 (14)	0.53391 (13)	0.4966 (13)	0.0834 (14)
H9	0.1323	0.5466	0.6030	0.100*
O1	0.0000	0.5000	0.9830 (7)	0.0529 (9)
O2	0.09910 (9)	0.47057 (7)	0.8266 (6)	0.0563 (7)
O3	0.18230 (10)	0.56356 (10)	0.3560 (9)	0.1276 (15)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.066 (3)	0.085 (3)	0.054 (3)	−0.002 (2)	−0.005 (3)	0.018 (2)
C2	0.059 (2)	0.061 (2)	0.062 (3)	−0.007 (2)	−0.011 (2)	0.023 (2)
C3	0.044 (2)	0.045 (2)	0.059 (3)	0.0026 (19)	−0.018 (2)	0.003 (2)
C4	0.060 (2)	0.044 (2)	0.083 (3)	−0.0005 (18)	−0.018 (3)	0.0096 (19)
C5	0.075 (3)	0.047 (2)	0.110 (4)	0.010 (2)	−0.029 (3)	−0.009 (3)
C6	0.069 (3)	0.066 (3)	0.084 (3)	0.013 (2)	−0.012 (3)	−0.014 (3)
C7	0.051 (3)	0.073 (3)	0.079 (3)	0.002 (2)	−0.006 (2)	0.007 (2)
C8	0.0426 (19)	0.049 (2)	0.066 (2)	0.0020 (18)	−0.014 (2)	0.011 (2)
C9	0.059 (3)	0.053 (3)	0.138 (4)	0.004 (2)	0.011 (3)	0.023 (3)
O1	0.0469 (17)	0.066 (2)	0.0457 (19)	−0.0031 (18)	0.000	0.000
O2	0.0481 (13)	0.0462 (13)	0.0746 (18)	−0.0005 (12)	0.0020 (13)	0.0170 (14)
O3	0.090 (2)	0.0707 (18)	0.222 (4)	0.0013 (17)	0.043 (3)	0.068 (2)

Geometric parameters (Å, º) top

C1—O1	1.429 (4)	C4—H4	0.9300
C1—C2	1.496 (5)	C5—C6	1.381 (5)
C1—H1A	0.9700	C5—H5	0.9300
C1—H1B	0.9700	C6—C7	1.377 (4)
C2—O2	1.436 (4)	C6—H6	0.9300
C2—H2A	0.9700	C7—C8	1.407 (5)
C2—H2B	0.9700	C7—H7	0.9300
C3—O2	1.368 (4)	C8—C9	1.466 (4)
C3—C4	1.398 (4)	C9—O3	1.194 (4)
C3—C8	1.405 (4)	C9—H9	0.9300
C4—C5	1.390 (5)	O1—C1ⁱ	1.429 (4)

O1—C1—C2	111.9 (3)	C6—C5—C4	121.7 (4)
O1—C1—H1A	109.2	C6—C5—H5	119.2
C2—C1—H1A	109.2	C4—C5—H5	119.2
O1—C1—H1B	109.2	C7—C6—C5	119.1 (4)
C2—C1—H1B	109.2	C7—C6—H6	120.4
H1A—C1—H1B	107.9	C5—C6—H6	120.4
O2—C2—C1	109.1 (3)	C6—C7—C8	121.0 (4)
O2—C2—H2A	109.9	C6—C7—H7	119.5
C1—C2—H2A	109.9	C8—C7—H7	119.5
O2—C2—H2B	109.9	C3—C8—C7	119.4 (3)
C1—C2—H2B	109.9	C3—C8—C9	121.1 (4)
H2A—C2—H2B	108.3	C7—C8—C9	119.5 (4)
O2—C3—C4	124.5 (3)	O3—C9—C8	125.7 (4)
O2—C3—C8	116.1 (3)	O3—C9—H9	117.2
C4—C3—C8	119.4 (3)	C8—C9—H9	117.2
C5—C4—C3	119.5 (3)	C1ⁱ—O1—C1	109.1 (4)
C5—C4—H4	120.2	C3—O2—C2	117.8 (2)
C3—C4—H4	120.2

O1—C1—C2—O2	69.3 (3)	C4—C3—C8—C9	179.4 (4)
O2—C3—C4—C5	−179.1 (3)	C6—C7—C8—C3	−0.8 (6)
C8—C3—C4—C5	0.7 (5)	C6—C7—C8—C9	−180.0 (4)
C3—C4—C5—C6	−1.0 (6)	C3—C8—C9—O3	−178.5 (4)
C4—C5—C6—C7	0.5 (6)	C7—C8—C9—O3	0.6 (7)
C5—C6—C7—C8	0.4 (6)	C2—C1—O1—C1ⁱ	176.7 (3)
O2—C3—C8—C7	−180.0 (3)	C4—C3—O2—C2	−3.0 (5)
C4—C3—C8—C7	0.2 (5)	C8—C3—O2—C2	177.2 (3)
O2—C3—C8—C9	−0.8 (5)	C1—C2—O2—C3	170.5 (3)

Symmetry code: (i) −x, −y+1, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O2	0.93	2.42	2.764 (5)	102

Experimental details

Crystal data
Chemical formula	C₁₈H₁₈O₅
M_r	314.32
Crystal system, space group	Orthorhombic, Fdd2
Temperature (K)	295
a, b, c (Å)	27.613 (6), 26.404 (5), 4.4313 (9)
V (Å³)	3230.8 (11)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.25 × 0.08 × 0.05

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	4449, 1043, 480
R_int	0.134
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.097, 0.99
No. of reflections	1043
No. of parameters	105
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.12, −0.14

Computer programs: COLLECT (Nonius, 1998), PHICHI (Duisenberg et al., 2000), EVAL14 (CCD) (Duisenberg et al., 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O2	0.93	2.42	2.764 (5)	102

Acknowledgements

The X-ray diffraction measurements were performed in the Laboratório de Difração de Raios X of the Universidade Federal Fluminense (LDRX-UFF), Niterói, Brazil. The authors thank CAPES, CNPq and FAPERJ for financial support. The co-editor is thanked for the transformation of the space group F2dd to the standard setting Fdd2, and for help with the solution and refinement of the structure.

References

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