2-[4-(2-Formyl­phen­oxy)­but­oxy]­benzaldehyde

Dehno Khalaji, A.; Hafez Ghoran, S.; Gotoh, K.; Ishida, H.

doi:10.1107/S1600536811034210

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2484

doi:10.1107/S1600536811034210

Open

access

2-[4-(2-Formylphenoxy)butoxy]benzaldehyde

Aliakbar Dehno Khalaji,^a Salar Hafez Ghoran,^a Kazuma Gotoh ^b and Hiroyuki Ishida ^b ^*

^aDepartment of Chemistry, Faculty of Science, Golestan University, Gorgan, Iran, and ^bDepartment of Chemistry, Faculty of Science, Okayama University, Okayama 700-8530, Japan
^*Correspondence e-mail: ishidah@cc.okayama-u.ac.jp

(Received 18 August 2011; accepted 20 August 2011; online 27 August 2011)

In the crystal structure of the title compound, C₁₈H₁₈O₄, the full molecule is generated by the application of an inversion centre. The molecule is essentially planar, with an r.m.s. deviation of 0.017 (1) Å for all non-H atoms. The molecules are linked through intermolecular C—H⋯O interactions to form a molecular sheet parallel to the ( $[\overline{1}]$ 02) plane.

Related literature

For the synthesis and related structures, see: Hu et al. (2005 ); Aravindan et al. (2003 ). For related literature on Schiff bases and their transition metal complexes, see: Ilhan et al. (2009 , 2010 ); Yilmaz et al. (2009 ).

Experimental

Crystal data

C₁₈H₁₈O₄
M_r = 298.34
Monoclinic, P 2₁ /c
a = 8.0624 (7) Å
b = 14.5896 (7) Å
c = 6.8003 (4) Å
β = 108.549 (4)°
V = 758.35 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 190 K
0.30 × 0.24 × 0.15 mm

Data collection

Rigaku R-AXIS RAPID II diffractometer
Absorption correction: numerical (NUMABS; Higashi, 1999 ) T_min = 0.980, T_max = 0.986
12149 measured reflections
2210 independent reflections
1243 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.132
S = 1.13
2210 reflections
100 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O1ⁱ	0.95	2.53	3.397 (2)	152
Symmetry code: (i) $[x+1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: PROCESS-AUTO (Rigaku/MSC, 2004 ); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: CrystalStructure and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811034210/tk2783sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811034210/tk2783Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811034210/tk2783Isup3.cml

checkCIF report

Comment top

In recent years, much attention has been paid to the synthesis and coordination chemistry of salicylaldehyde, its Schiff base derivatives and transition metal complexes (Hu et al., 2005; Aravindan et al., 2003; Ilhan et al., 2009, 2010; Yilmaz et al., 2009). The two-arm aldehydes can be condensed with primary diamines to form macrocyclic Schiff base ligands (Ilhan et al., 2009, 2010; Yilmaz et al., 2009).

In the crystal structure, the title molecule, 2,2'-[butane-1,4-diylbis(oxy)]dibenzaldehyde (Fig. 1), lies on a crystallographic inversion center, thus indicating that one half the molecule comprises the asymmetric unit. The molecules are linked through intermolecular C3—H3···O1ⁱⁱ contacts (Table 1), resulting in a molecular sheet parallel to the (102) plane (Fig. 2).

Related literature top

For the synthesis and related structures, see: Hu et al. (2005); Aravindan et al. (2003). For related literature on Schiff bases and their transition metal complexes, see: Ilhan et al. (2009, 2010); Yilmaz et al. (2009).

Experimental top

The title compound was isolated from the reaction between salicylaldehyde and butane-1,4-diamine in the presence of K₂CO₃ at 85 °C for about 48 h according to the literature (Hu et al., 2005). A small amount of the precipitate was dissolved in a mixture of methanol-chloroform (1:1 v/v) to make a clear solution and kept at room temperature for 3 days to give single crystals suitable for X-ray diffraction.

Computing details top

Data collection: PROCESS-AUTO (Rigaku/MSC, 2004); cell refinement: PROCESS-AUTO (Rigaku/MSC, 2004); data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2004) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids of non-H atoms are drawn at the 50% probability level.
	Fig. 2. A packing diagram of the title compound, showing a molecular sheet formed by C—H···O hydrogen bonds (dashed lines).

2-[4-(2-Formylphenoxy)butoxy]benzaldehyde top

Crystal data top

C₁₈H₁₈O₄	F(000) = 316.00
M_r = 298.34	D_x = 1.306 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2ybc	Cell parameters from 7072 reflections
a = 8.0624 (7) Å	θ = 3.0–30.1°
b = 14.5896 (7) Å	µ = 0.09 mm⁻¹
c = 6.8003 (4) Å	T = 190 K
β = 108.549 (4)°	Block, pale-yellow
V = 758.35 (8) Å³	0.30 × 0.24 × 0.15 mm
Z = 2

Data collection top

Rigaku R-AXIS RAPID II diffractometer	1243 reflections with I > 2σ(I)
Detector resolution: 10.00 pixels mm^-1	R_int = 0.041
ω scans	θ_max = 30.0°
Absorption correction: numerical (NUMABS; Higashi, 1999)	h = −11→11
T_min = 0.980, T_max = 0.986	k = −20→20
12149 measured reflections	l = −9→9
2210 independent reflections

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.132	H-atom parameters constrained
S = 1.13	w = 1/[σ²(F_o²) + (0.0563P)² + 0.0806P] where P = (F_o² + 2F_c²)/3
2210 reflections	(Δ/σ)_max = 0.0001
100 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₈H₁₈O₄	V = 758.35 (8) Å³
M_r = 298.34	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.0624 (7) Å	µ = 0.09 mm⁻¹
b = 14.5896 (7) Å	T = 190 K
c = 6.8003 (4) Å	0.30 × 0.24 × 0.15 mm
β = 108.549 (4)°

Data collection top

Rigaku R-AXIS RAPID II diffractometer	2210 independent reflections
Absorption correction: numerical (NUMABS; Higashi, 1999)	1243 reflections with I > 2σ(I)
T_min = 0.980, T_max = 0.986	R_int = 0.041
12149 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.132	H-atom parameters constrained
S = 1.13	Δρ_max = 0.29 e Å⁻³
2210 reflections	Δρ_min = −0.24 e Å⁻³
100 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
O1	0.18122 (15)	0.33844 (8)	0.1640 (2)	0.0554 (4)
O2	0.69626 (12)	0.36790 (7)	0.37956 (16)	0.0343 (3)
C1	0.45915 (17)	0.26677 (9)	0.2840 (2)	0.0307 (3)
C2	0.64045 (18)	0.27981 (9)	0.3598 (2)	0.0297 (3)
C3	0.75273 (18)	0.20492 (10)	0.4082 (2)	0.0327 (3)
H3	0.8758	0.2135	0.4596	0.039*
C4	0.6825 (2)	0.11807 (10)	0.3803 (2)	0.0380 (4)
H4	0.7586	0.0666	0.4134	0.046*
C5	0.5042 (2)	0.10385 (11)	0.3054 (3)	0.0411 (4)
H5	0.4582	0.0434	0.2868	0.049*
C6	0.3940 (2)	0.17801 (10)	0.2582 (2)	0.0380 (4)
H6	0.2712	0.1684	0.2071	0.046*
C7	0.3391 (2)	0.34439 (11)	0.2358 (3)	0.0396 (4)
H7	0.3882	0.4041	0.2625	0.047*
C8	0.88087 (17)	0.38476 (10)	0.4570 (2)	0.0333 (3)
H8A	0.9405	0.3547	0.3674	0.040*
H8B	0.9307	0.3604	0.5996	0.040*
C9	0.90444 (18)	0.48669 (10)	0.4558 (2)	0.0350 (4)
H9A	0.8379	0.5159	0.5387	0.042*
H9B	0.8568	0.5096	0.3117	0.042*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0243 (6)	0.0575 (8)	0.0782 (9)	0.0011 (5)	0.0074 (6)	−0.0063 (6)
O2	0.0210 (5)	0.0285 (5)	0.0497 (6)	−0.0040 (4)	0.0060 (4)	−0.0021 (4)
C1	0.0234 (7)	0.0324 (8)	0.0352 (7)	−0.0038 (5)	0.0077 (6)	−0.0030 (6)
C2	0.0268 (7)	0.0287 (7)	0.0333 (7)	−0.0051 (5)	0.0092 (6)	−0.0032 (6)
C3	0.0244 (7)	0.0320 (8)	0.0391 (8)	−0.0013 (6)	0.0065 (6)	−0.0020 (6)
C4	0.0358 (8)	0.0316 (8)	0.0447 (9)	0.0011 (6)	0.0102 (7)	0.0001 (7)
C5	0.0363 (8)	0.0317 (8)	0.0521 (9)	−0.0074 (6)	0.0095 (7)	−0.0039 (7)
C6	0.0286 (8)	0.0388 (9)	0.0441 (9)	−0.0085 (6)	0.0081 (7)	−0.0055 (7)
C7	0.0265 (8)	0.0372 (9)	0.0529 (10)	−0.0018 (6)	0.0095 (7)	−0.0027 (7)
C8	0.0206 (7)	0.0313 (7)	0.0453 (8)	−0.0026 (5)	0.0068 (6)	−0.0035 (6)
C9	0.0239 (7)	0.0294 (7)	0.0489 (9)	−0.0023 (6)	0.0075 (6)	−0.0035 (6)

Geometric parameters (Å, º) top

O1—C7	1.2128 (18)	C5—C6	1.372 (2)
O2—C2	1.3543 (16)	C5—H5	0.9500
O2—C8	1.4333 (16)	C6—H6	0.9500
C1—C6	1.3874 (19)	C7—H7	0.9500
C1—C2	1.3997 (19)	C8—C9	1.500 (2)
C1—C7	1.458 (2)	C8—H8A	0.9900
C2—C3	1.390 (2)	C8—H8B	0.9900
C3—C4	1.376 (2)	C9—C9ⁱ	1.516 (3)
C3—H3	0.9500	C9—H9A	0.9900
C4—C5	1.379 (2)	C9—H9B	0.9900
C4—H4	0.9500

C2—O2—C8	118.21 (11)	C5—C6—H6	119.5
C6—C1—C2	118.83 (13)	C1—C6—H6	119.5
C6—C1—C7	119.95 (13)	O1—C7—C1	124.87 (14)
C2—C1—C7	121.21 (12)	O1—C7—H7	117.6
O2—C2—C3	123.48 (13)	C1—C7—H7	117.6
O2—C2—C1	116.14 (12)	O2—C8—C9	106.66 (11)
C3—C2—C1	120.37 (12)	O2—C8—H8A	110.4
C4—C3—C2	118.85 (13)	C9—C8—H8A	110.4
C4—C3—H3	120.6	O2—C8—H8B	110.4
C2—C3—H3	120.6	C9—C8—H8B	110.4
C3—C4—C5	121.62 (14)	H8A—C8—H8B	108.6
C3—C4—H4	119.2	C8—C9—C9ⁱ	111.50 (15)
C5—C4—H4	119.2	C8—C9—H9A	109.3
C6—C5—C4	119.28 (14)	C9ⁱ—C9—H9A	109.3
C6—C5—H5	120.4	C8—C9—H9B	109.3
C4—C5—H5	120.4	C9ⁱ—C9—H9B	109.3
C5—C6—C1	121.05 (14)	H9A—C9—H9B	108.0

C8—O2—C2—C3	−0.8 (2)	C3—C4—C5—C6	−0.2 (2)
C8—O2—C2—C1	179.88 (12)	C4—C5—C6—C1	0.2 (2)
C6—C1—C2—O2	179.34 (12)	C2—C1—C6—C5	−0.1 (2)
C7—C1—C2—O2	−1.8 (2)	C7—C1—C6—C5	−179.02 (15)
C6—C1—C2—C3	0.0 (2)	C6—C1—C7—O1	−3.4 (3)
C7—C1—C2—C3	178.91 (14)	C2—C1—C7—O1	177.73 (16)
O2—C2—C3—C4	−179.30 (13)	C2—O2—C8—C9	178.18 (12)
C1—C2—C3—C4	0.0 (2)	O2—C8—C9—C9ⁱ	177.46 (15)
C2—C3—C4—C5	0.1 (2)

Symmetry code: (i) −x+2, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1ⁱⁱ	0.95	2.53	3.397 (2)	152

Symmetry code: (ii) x+1, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₈O₄
M_r	298.34
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	190
a, b, c (Å)	8.0624 (7), 14.5896 (7), 6.8003 (4)
β (°)	108.549 (4)
V (Å³)	758.35 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.24 × 0.15

Data collection
Diffractometer	Rigaku R-AXIS RAPID II diffractometer
Absorption correction	Numerical (NUMABS; Higashi, 1999)
T_min, T_max	0.980, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	12149, 2210, 1243
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.704

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.132, 1.13
No. of reflections	2210
No. of parameters	100
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.24

Computer programs: PROCESS-AUTO (Rigaku/MSC, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), CrystalStructure (Rigaku/MSC, 2004) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1ⁱ	0.95	2.53	3.397 (2)	152

Symmetry code: (i) x+1, −y+1/2, z+1/2.

Acknowledgements

This work was partly supported by a Grant-in-Aid for Scientific Research (C) (No. 22550013) from the Japan Society for the Promotion of Science. We also acknowledge Golestan University for partial support of this work.

References

Aravindan, P. G., Yogavel, M., Thirumavalavan, M., Akilan, P., Velmurugan, D., Kandaswamy, M., Shanmuga Sundara Raj, S. & Fun, H.-K. (2003). Acta Cryst. E59, o806–o807. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Higashi, T. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan. Google Scholar
Hu, P.-Z., Ma, L.-F., Wang, J.-G., Zhao, B.-T. & Wang, L.-Y. (2005). Acta Cryst. E61, o2775–o2777. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ilhan, S., Temel, H. & Pasa, S. (2009). Chin. Chem. Lett. 20, 339–343. CrossRef CAS Google Scholar
Ilhan, S., Temel, H., Pasa, S. & Tegin, I. (2010). Russ. J. Coord. Chem. 55, 1402–1409. CAS Google Scholar
Rigaku/MSC (2004). PROCESS-AUTO and CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yilmaz, I., Ilhan, S., Temel, H. & Kilic, A. (2009). J. Incl. Phenom. Macrocycl. Chem. 63, 163–169. CrossRef CAS Google Scholar