4-{2-[2-(4-Formyl-phen-oxy)eth-oxy]eth-oxy}benzaldehyde.

The title compound, C(18)H(18)O(5), was obtained by the reaction of 4-hy-droxy-benzaldehyde with bis-(2,2-dichloro-eth-yl) ether in dimethyl-formamide. In the crystal, the mol-ecule lies on a twofold rotation axis that passes through the central O atom of the aliphatic chain, thus leading to one half-mol-ecule being present per asymmetric unit. The carbonyl, aryl and O-CH(2)-CH(2) groups are almost coplanar, with an r.m.s. deviation of 0.030 Å. The aromatic rings are approximately perpendicular to each other, forming a dihedral angle of 78.31 sh;H⋯O hydrogen bonds and C-H⋯π inter-actions help to consolidate the three-dimensional network.

Related literature

For the synthesis and structures of dialdehydes, see Aravindan et al. (2003 ▶); Han & Zhen (2005 ▶); Ma & Liu (2002 ▶), Qi et al. (2005 ▶). For properties and applications of dialdehydes, see: Ma & Liu (2003a ▶,b ▶); Ma & Cao (2005 ▶); Ragunathan & Bharadwaj (1992 ▶); Ray & Bharadwaj (2006 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C18H18O5

M = 314.32

Monoclinic,

a = 15.309 (2) Å

b = 4.5653 (6) Å

c = 11.8332 (15) Å

β = 113.253 (7)°

V = 759.85 (17) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.32 × 0.26 × 0.23 mm

Data collection

Bruekr SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.969, T max = 0.977

8239 measured reflections

1566 independent reflections

1374 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.101

S = 1.07

1566 reflections

105 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; 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: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811018150/zl2368sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811018150/zl2368Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811018150/zl2368Isup3.cml

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

C18H18O5	F(000) = 332
Mr = 314.32	Dx = 1.374 Mg m−3
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C2y	Cell parameters from 8239 reflections
a = 15.309 (2) Å	θ = 2.8–33.2°
b = 4.5653 (6) Å	µ = 0.10 mm−1
c = 11.8332 (15) Å	T = 298 K
β = 113.253 (7)°	Prism, colorless
V = 759.85 (17) Å3	0.32 × 0.26 × 0.23 mm
Z = 2

Bruekr SMART CCD area-detector diffractometer	1566 independent reflections
Radiation source: fine-focus sealed tube	1374 reflections with I > 2σ(I)
Graphite Monochromator	Rint = 0.026
Detector resolution: 0 pixels mm-1	θmax = 33.2°, θmin = 2.8°
φ and ω scans	h = −22→22
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −6→6
Tmin = 0.969, Tmax = 0.977	l = −18→17
8239 measured 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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0634P)2 + 0.1116P] where P = (Fo2 + 2Fc2)/3
1566 reflections	(Δ/σ)max < 0.001
105 parameters	Δρmax = 0.35 e Å−3
1 restraint	Δρmin = −0.19 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
O2	0.11077 (6)	0.9413 (2)	0.36300 (8)	0.0224 (2)
O3	0.0000	1.0762 (3)	0.5000	0.0188 (3)
C8	0.01664 (9)	1.0616 (3)	0.30796 (12)	0.0202 (2)
H8A	−0.0303	0.9059	0.2837	0.024*
H8B	0.0095	1.1751	0.2356	0.024*
C2	0.21612 (9)	0.3700 (3)	0.17623 (12)	0.0196 (3)
C5	0.14083 (9)	0.7593 (3)	0.29553 (11)	0.0180 (2)
C4	0.23027 (9)	0.6328 (3)	0.35916 (12)	0.0214 (3)
H4A	0.2646	0.6791	0.4414	0.026*
C7	0.12779 (9)	0.4969 (3)	0.11397 (12)	0.0219 (3)
H7A	0.0936	0.4503	0.0317	0.026*
C1	0.25348 (10)	0.1644 (3)	0.11128 (13)	0.0246 (3)
H1A	0.2136	0.1144	0.0313	0.029*
C6	0.08902 (9)	0.6923 (3)	0.17174 (11)	0.0207 (3)
H6A	0.0298	0.7767	0.1288	0.025*
O1	0.33176 (7)	0.0537 (3)	0.15259 (10)	0.0313 (3)
C9	0.00335 (10)	1.2542 (3)	0.40302 (12)	0.0215 (3)
H9A	0.0556	1.3920	0.4353	0.026*
H9B	−0.0553	1.3645	0.3659	0.026*
C3	0.26761 (9)	0.4399 (3)	0.30040 (12)	0.0211 (3)
H3A	0.3270	0.3561	0.3431	0.025*

	U11	U22	U33	U12	U13	U23
O2	0.0160 (4)	0.0308 (5)	0.0187 (4)	0.0001 (4)	0.0050 (3)	−0.0039 (4)
O3	0.0237 (6)	0.0179 (6)	0.0170 (6)	0.000	0.0105 (5)	0.000
C8	0.0179 (5)	0.0244 (6)	0.0173 (5)	0.0009 (5)	0.0060 (4)	0.0024 (5)
C2	0.0208 (6)	0.0204 (6)	0.0186 (6)	−0.0009 (5)	0.0088 (5)	0.0009 (5)
C5	0.0167 (5)	0.0210 (6)	0.0168 (5)	−0.0032 (5)	0.0073 (4)	0.0003 (5)
C4	0.0173 (5)	0.0288 (7)	0.0159 (5)	−0.0016 (5)	0.0040 (4)	−0.0003 (5)
C7	0.0221 (6)	0.0264 (7)	0.0152 (6)	−0.0008 (5)	0.0051 (5)	−0.0001 (5)
C1	0.0291 (6)	0.0239 (6)	0.0212 (6)	0.0019 (5)	0.0105 (5)	0.0006 (5)
C6	0.0169 (5)	0.0264 (7)	0.0158 (5)	0.0005 (5)	0.0033 (4)	−0.0002 (5)
O1	0.0307 (5)	0.0330 (6)	0.0315 (6)	0.0073 (5)	0.0136 (4)	−0.0004 (5)
C9	0.0250 (6)	0.0191 (6)	0.0222 (6)	0.0013 (5)	0.0112 (5)	0.0029 (5)
C3	0.0165 (5)	0.0257 (6)	0.0195 (6)	0.0003 (5)	0.0055 (4)	0.0025 (5)

O2—C5	1.3528 (16)	C5—C4	1.4004 (18)
O2—C8	1.4357 (15)	C4—C3	1.378 (2)
O3—C9i	1.4235 (16)	C4—H4A	0.9300
O3—C9	1.4235 (16)	C7—C6	1.3915 (19)
C8—C9	1.504 (2)	C7—H7A	0.9300
C8—H8A	0.9700	C1—O1	1.2114 (17)
C8—H8B	0.9700	C1—H1A	0.9300
C2—C7	1.3857 (18)	C6—H6A	0.9300
C2—C3	1.4027 (18)	C9—H9A	0.9700
C2—C1	1.465 (2)	C9—H9B	0.9700
C5—C6	1.3967 (17)	C3—H3A	0.9300
C5—O2—C8	118.79 (10)	C2—C7—H7A	119.2
C9i—O3—C9	110.38 (15)	C6—C7—H7A	119.2
O2—C8—C9	107.00 (11)	O1—C1—C2	125.76 (13)
O2—C8—H8A	110.3	O1—C1—H1A	117.1
C9—C8—H8A	110.3	C2—C1—H1A	117.1
O2—C8—H8B	110.3	C7—C6—C5	118.66 (12)
C9—C8—H8B	110.3	C7—C6—H6A	120.7
H8A—C8—H8B	108.6	C5—C6—H6A	120.7
C7—C2—C3	119.25 (12)	O3—C9—C8	109.13 (12)
C7—C2—C1	119.35 (12)	O3—C9—H9A	109.9
C3—C2—C1	121.40 (12)	C8—C9—H9A	109.9
O2—C5—C6	124.66 (12)	O3—C9—H9B	109.9
O2—C5—C4	115.10 (11)	C8—C9—H9B	109.9
C6—C5—C4	120.24 (12)	H9A—C9—H9B	108.3
C3—C4—C5	120.29 (12)	C4—C3—C2	120.03 (12)
C3—C4—H4A	119.9	C4—C3—H3A	120.0
C5—C4—H4A	119.9	C2—C3—H3A	120.0
C2—C7—C6	121.53 (12)
C5—O2—C8—C9	−179.71 (11)	C2—C7—C6—C5	−0.3 (2)
C8—O2—C5—C6	4.4 (2)	O2—C5—C6—C7	−178.83 (13)
C8—O2—C5—C4	−174.93 (12)	C4—C5—C6—C7	0.5 (2)
O2—C5—C4—C3	178.97 (12)	C9i—O3—C9—C8	174.42 (13)
C6—C5—C4—C3	−0.4 (2)	O2—C8—C9—O3	−68.53 (13)
C3—C2—C7—C6	0.1 (2)	C5—C4—C3—C2	0.2 (2)
C1—C2—C7—C6	179.68 (12)	C7—C2—C3—C4	0.0 (2)
C7—C2—C1—O1	174.98 (15)	C1—C2—C3—C4	−179.59 (13)
C3—C2—C1—O1	−5.4 (2)

Cg is the centroid of the C2–C7 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9B···O1ii	0.97	2.58	3.3772 (18)	139
C4—H4A···O2iii	0.93	2.59	3.3434 (16)	139
C8—H8B···Cgiv	0.97	3.14	3.7172 (14)	129

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C2–C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9B⋯O1i	0.97	2.58	3.3772 (18)	139
C4—H4A⋯O2ii	0.93	2.59	3.3434 (16)	139
C8—H8B⋯Cgiii	0.97	3.14	3.7172 (14)	129

Symmetry codes: (i) ; (ii) ; (iii) .