2-[4-(2-Formyl-phen-oxy)-but-oxy]-benzaldehyde.

In the crystal structure of the title compound, C(18)H(18)O(4), the full mol-ecule is generated by the application of an inversion centre. The mol-ecule is essentially planar, with an r.m.s. deviation of 0.017 (1) Å for all non-H atoms. The mol-ecules are linked through inter-molecular C-H⋯O inter-actions to form a mol-ecular sheet parallel to the ([Formula: see text]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 = 298.34

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.132

S = 1.13

2210 reflections

100 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.24 e Å−3

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811034210/tk2783sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811034210/tk2783Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C18H18O4	F(000) = 316.00
Mr = 298.34	Dx = 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

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

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(Fo2) + (0.0563P)2 + 0.0806P] where P = (Fo2 + 2Fc2)/3
2210 reflections	(Δ/σ)max = 0.0001
100 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.24 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	Uiso*/Ueq
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*

	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)

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)

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

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) .