4,4′-(Propane-1,3-diyldi­oxy)dibenz­aldehyde

Ali, Q.; Raza Shah, M.; Ng, S.W.

doi:10.1107/S1600536810021124

organic compounds

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Volume 66| Part 7| July 2010| Page o1620

doi:10.1107/S1600536810021124

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4,4′-(Propane-1,3-diyldioxy)dibenzaldehyde

Qamar Ali,^a Muhammad Raza Shah ^a and Seik Weng Ng ^b ^*

^aHEJ Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 2 June 2010; accepted 3 June 2010; online 9 June 2010)

The title compound, C₁₇H₁₆O₄, is a dialdehyde in which two formylphenoxy units are linked by a –CH₂CH₂CH₂– chain; the molecule is V-shaped with the middle methylene C atom as the apex. The two benzene rings are aligned at 77.4 (1)°. In the crystal, molecules are linked into centrosymmetric dimers by pairs of non-classical C—H⋯O hydrogen bonds.

Related literature

For background to Schiff bases derived by condensing similar dialdehydes with primary amines, see: Zhang et al. (2008 ). For the crystal structure of the 2,2′-disubstituted analog, see: Hu et al. (2005 ).

Experimental

Crystal data

C₁₇H₁₆O₄
M_r = 284.30
Monoclinic, P 2₁ /n
a = 15.3323 (15) Å
b = 4.6173 (5) Å
c = 20.2800 (19) Å
β = 104.783 (1)°
V = 1388.2 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.25 × 0.20 × 0.10 mm

Data collection

Bruker SMART APEXII diffractometer
8297 measured reflections
3113 independent reflections
2538 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.106
S = 1.03
3113 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16⋯O1ⁱ	0.95	2.41	3.287 (2)	154
Symmetry code: (i) -x+1, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810021124/ci5094sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810021124/ci5094Isup2.hkl

checkCIF report

Comment top

The two-arm aldehyde is intended for condensation with primary amines to form Schiff bases, which, in a subsequent step, will be reacted with β-cyclodextrin to furnish inclusion compounds. The idea for this theme draws on a report on such compounds of poly(Schiff bases) (Zhang et al., 2008). The flexibilty of the Schiff base can be controlled by varying the position of the formyl group; the title compound has the the formyl groups in the 4,4'-positions. The crystal structure of the 2,2'-substituted compound has been reported (Hu et al., 2005). The molecule of C₁₇H₁₆O₄ (Scheme I) is V-shaped with the middle methylene carbon as the apex (Fig. 1).

Related literature top

For background to Schiff bases derived by condensing similar dialdehydes with primary amines, see: Zhang et al. (2008). For the crystal structure of the 2,2'-disubstituted analog, see: Hu et al. (2005).

Experimental top

4-Hydroxybenzaldehyde (1 g, 8.2 mmol) was dissolved in acetone (25 ml). To the solution was added potassium carbonate (2.3 g, 16.4 mmol). The mixture was heated for 1 h. 1,3-Dibromopropane (0.29 ml, 2.7 mmol) was added and the mixture heated for another hour. The mixture was set aside for 8 h. The solvent was removed and the solid material was extracted with ethyl acetate. The solvent was again removed and the product purified by column chromatography by using dichloromethane-hexane (1:4) as mobile phase. Single crystals were obtained by recrystallization from dichloromethane.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Displacement ellipsoid plot (Barbour, 2001) of C₁₇H₁₆O₄ at the 70% probability level; H atoms are drawn as spheres of arbitrary radius.

4,4'-(Propane-1,3-diyldioxy)dibenzaldehyde top

Crystal data top

C₁₇H₁₆O₄	F(000) = 600
M_r = 284.30	D_x = 1.360 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2677 reflections
a = 15.3323 (15) Å	θ = 3.1–28.0°
b = 4.6173 (5) Å	µ = 0.10 mm⁻¹
c = 20.2800 (19) Å	T = 100 K
β = 104.783 (1)°	Plate, colourless
V = 1388.2 (2) Å³	0.25 × 0.20 × 0.10 mm
Z = 4

Data collection top

Bruker SMART APEXII diffractometer	2538 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.027
Graphite monochromator	θ_max = 27.5°, θ_min = 1.5°
ω scans	h = −19→19
8297 measured reflections	k = −5→5
3113 independent reflections	l = −19→26

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.106	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0513P)² + 0.4617P] where P = (F_o² + 2F_c²)/3
3113 reflections	(Δ/σ)_max = 0.001
190 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₇H₁₆O₄	V = 1388.2 (2) Å³
M_r = 284.30	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 15.3323 (15) Å	µ = 0.10 mm⁻¹
b = 4.6173 (5) Å	T = 100 K
c = 20.2800 (19) Å	0.25 × 0.20 × 0.10 mm
β = 104.783 (1)°

Data collection top

Bruker SMART APEXII diffractometer	2538 reflections with I > 2σ(I)
8297 measured reflections	R_int = 0.027
3113 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.106	H-atom parameters constrained
S = 1.03	Δρ_max = 0.25 e Å⁻³
3113 reflections	Δρ_min = −0.22 e Å⁻³
190 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.33791 (6)	1.4272 (2)	0.27971 (5)	0.0247 (2)
O2	0.37445 (6)	0.5332 (2)	0.52487 (5)	0.0191 (2)
O3	0.36450 (6)	0.5695 (2)	0.70403 (5)	0.0191 (2)
O4	0.58320 (6)	1.2514 (2)	0.97043 (5)	0.0290 (3)
C1	0.28543 (9)	1.3387 (3)	0.31097 (7)	0.0193 (3)
H1	0.2260	1.4154	0.2992	0.023*
C2	0.30737 (8)	1.1217 (3)	0.36563 (7)	0.0171 (3)
C3	0.24107 (8)	1.0286 (3)	0.39613 (7)	0.0183 (3)
H3	0.1816	1.1028	0.3805	0.022*
C4	0.25983 (8)	0.8289 (3)	0.44913 (7)	0.0182 (3)
H4	0.2137	0.7657	0.4694	0.022*
C5	0.34744 (8)	0.7227 (3)	0.47213 (6)	0.0166 (3)
C6	0.41484 (8)	0.8113 (3)	0.44128 (7)	0.0188 (3)
H6	0.4742	0.7361	0.4566	0.023*
C7	0.39463 (9)	1.0082 (3)	0.38860 (7)	0.0192 (3)
H7	0.4404	1.0678	0.3676	0.023*
C8	0.30783 (8)	0.4333 (3)	0.55834 (7)	0.0182 (3)
H8A	0.2590	0.3283	0.5257	0.022*
H8B	0.2810	0.5991	0.5771	0.022*
C9	0.35588 (9)	0.2331 (3)	0.61526 (7)	0.0190 (3)
H9A	0.3901	0.0869	0.5964	0.023*
H9B	0.3103	0.1290	0.6331	0.023*
C10	0.42019 (8)	0.3892 (3)	0.67370 (7)	0.0176 (3)
H10A	0.4544	0.2486	0.7074	0.021*
H10B	0.4635	0.5084	0.6567	0.021*
C11	0.40426 (8)	0.7236 (3)	0.76107 (6)	0.0164 (3)
C12	0.34516 (8)	0.8830 (3)	0.78886 (7)	0.0189 (3)
H12	0.2821	0.8762	0.7685	0.023*
C13	0.37858 (9)	1.0507 (3)	0.84602 (7)	0.0202 (3)
H13	0.3383	1.1611	0.8647	0.024*
C14	0.47139 (8)	1.0595 (3)	0.87679 (7)	0.0187 (3)
C15	0.52930 (8)	0.8986 (3)	0.84844 (7)	0.0189 (3)
H15	0.5923	0.9038	0.8691	0.023*
C16	0.49718 (8)	0.7308 (3)	0.79069 (7)	0.0174 (3)
H16	0.5375	0.6227	0.7716	0.021*
C17	0.50495 (9)	1.2379 (3)	0.93787 (7)	0.0235 (3)
H17	0.4622	1.3516	0.9531	0.028*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0269 (5)	0.0271 (5)	0.0213 (5)	0.0011 (4)	0.0081 (4)	0.0041 (4)
O2	0.0179 (4)	0.0231 (5)	0.0158 (5)	0.0023 (4)	0.0036 (4)	0.0036 (4)
O3	0.0165 (4)	0.0234 (5)	0.0163 (5)	0.0004 (4)	0.0020 (3)	−0.0030 (4)
O4	0.0248 (5)	0.0375 (6)	0.0228 (6)	−0.0053 (4)	0.0027 (4)	−0.0083 (5)
C1	0.0220 (6)	0.0177 (6)	0.0168 (7)	0.0004 (5)	0.0027 (5)	−0.0033 (5)
C2	0.0200 (6)	0.0162 (6)	0.0139 (6)	−0.0002 (5)	0.0020 (5)	−0.0036 (5)
C3	0.0168 (6)	0.0190 (6)	0.0169 (7)	0.0015 (5)	0.0006 (5)	−0.0027 (5)
C4	0.0171 (6)	0.0207 (6)	0.0165 (7)	−0.0013 (5)	0.0039 (5)	−0.0019 (5)
C5	0.0197 (6)	0.0166 (6)	0.0118 (6)	0.0005 (5)	0.0010 (5)	−0.0027 (5)
C6	0.0166 (6)	0.0212 (7)	0.0177 (7)	0.0022 (5)	0.0026 (5)	−0.0018 (5)
C7	0.0189 (6)	0.0211 (7)	0.0180 (7)	−0.0012 (5)	0.0055 (5)	−0.0017 (5)
C8	0.0187 (6)	0.0199 (7)	0.0158 (7)	−0.0021 (5)	0.0039 (5)	−0.0018 (5)
C9	0.0208 (6)	0.0174 (6)	0.0181 (7)	−0.0019 (5)	0.0035 (5)	−0.0009 (5)
C10	0.0184 (6)	0.0182 (6)	0.0160 (7)	0.0010 (5)	0.0038 (5)	−0.0005 (5)
C11	0.0191 (6)	0.0155 (6)	0.0135 (6)	−0.0013 (5)	0.0022 (5)	0.0025 (5)
C12	0.0154 (6)	0.0218 (7)	0.0192 (7)	−0.0006 (5)	0.0037 (5)	0.0012 (5)
C13	0.0194 (6)	0.0205 (7)	0.0221 (7)	0.0011 (5)	0.0077 (5)	−0.0014 (6)
C14	0.0205 (6)	0.0190 (6)	0.0163 (7)	−0.0018 (5)	0.0037 (5)	0.0006 (5)
C15	0.0160 (6)	0.0204 (7)	0.0186 (7)	−0.0006 (5)	0.0015 (5)	0.0027 (5)
C16	0.0165 (6)	0.0190 (6)	0.0173 (7)	0.0016 (5)	0.0053 (5)	0.0009 (5)
C17	0.0242 (7)	0.0258 (7)	0.0214 (7)	−0.0022 (6)	0.0073 (5)	−0.0026 (6)

Geometric parameters (Å, º) top

O1—C1	1.2152 (16)	C8—H8A	0.99
O2—C5	1.3620 (15)	C8—H8B	0.99
O2—C8	1.4389 (15)	C9—C10	1.5167 (17)
O3—C11	1.3623 (15)	C9—H9A	0.99
O3—C10	1.4382 (15)	C9—H9B	0.99
O4—C17	1.2145 (17)	C10—H10A	0.99
C1—C2	1.4682 (19)	C10—H10B	0.99
C1—H1	0.95	C11—C12	1.3931 (18)
C2—C3	1.3863 (18)	C11—C16	1.3981 (17)
C2—C7	1.4014 (18)	C12—C13	1.3796 (19)
C3—C4	1.3894 (19)	C12—H12	0.95
C3—H3	0.95	C13—C14	1.4009 (17)
C4—C5	1.3938 (18)	C13—H13	0.95
C4—H4	0.95	C14—C15	1.3895 (19)
C5—C6	1.3989 (18)	C14—C17	1.4674 (19)
C6—C7	1.3765 (19)	C15—C16	1.3859 (18)
C6—H6	0.95	C15—H15	0.95
C7—H7	0.95	C16—H16	0.95
C8—C9	1.5153 (18)	C17—H17	0.95

C5—O2—C8	117.78 (10)	C10—C9—H9A	108.9
C11—O3—C10	118.66 (9)	C8—C9—H9B	108.9
O1—C1—C2	124.65 (12)	C10—C9—H9B	108.9
O1—C1—H1	117.7	H9A—C9—H9B	107.7
C2—C1—H1	117.7	O3—C10—C9	105.71 (10)
C3—C2—C7	118.83 (12)	O3—C10—H10A	110.6
C3—C2—C1	119.72 (11)	C9—C10—H10A	110.6
C7—C2—C1	121.44 (12)	O3—C10—H10B	110.6
C2—C3—C4	121.36 (12)	C9—C10—H10B	110.6
C2—C3—H3	119.3	H10A—C10—H10B	108.7
C4—C3—H3	119.3	O3—C11—C12	115.02 (11)
C3—C4—C5	118.95 (12)	O3—C11—C16	124.28 (11)
C3—C4—H4	120.5	C12—C11—C16	120.69 (12)
C5—C4—H4	120.5	C13—C12—C11	119.74 (11)
O2—C5—C4	124.25 (12)	C13—C12—H12	120.1
O2—C5—C6	115.34 (11)	C11—C12—H12	120.1
C4—C5—C6	120.40 (12)	C12—C13—C14	120.51 (12)
C7—C6—C5	119.66 (12)	C12—C13—H13	119.7
C7—C6—H6	120.2	C14—C13—H13	119.7
C5—C6—H6	120.2	C15—C14—C13	118.95 (12)
C6—C7—C2	120.77 (12)	C15—C14—C17	121.73 (12)
C6—C7—H7	119.6	C13—C14—C17	119.32 (12)
C2—C7—H7	119.6	C16—C15—C14	121.44 (12)
O2—C8—C9	106.81 (10)	C16—C15—H15	119.3
O2—C8—H8A	110.4	C14—C15—H15	119.3
C9—C8—H8A	110.4	C15—C16—C11	118.67 (12)
O2—C8—H8B	110.4	C15—C16—H16	120.7
C9—C8—H8B	110.4	C11—C16—H16	120.7
H8A—C8—H8B	108.6	O4—C17—C14	124.94 (13)
C8—C9—C10	113.45 (11)	O4—C17—H17	117.5
C8—C9—H9A	108.9	C14—C17—H17	117.5

O1—C1—C2—C3	−177.57 (13)	C11—O3—C10—C9	176.03 (10)
O1—C1—C2—C7	3.3 (2)	C8—C9—C10—O3	65.84 (13)
C7—C2—C3—C4	0.75 (19)	C10—O3—C11—C12	−177.41 (11)
C1—C2—C3—C4	−178.41 (12)	C10—O3—C11—C16	3.47 (18)
C2—C3—C4—C5	0.48 (19)	O3—C11—C12—C13	−178.89 (12)
C8—O2—C5—C4	0.89 (18)	C16—C11—C12—C13	0.26 (19)
C8—O2—C5—C6	−179.69 (11)	C11—C12—C13—C14	−0.7 (2)
C3—C4—C5—O2	178.02 (12)	C12—C13—C14—C15	0.6 (2)
C3—C4—C5—C6	−1.37 (19)	C12—C13—C14—C17	−179.52 (13)
O2—C5—C6—C7	−178.41 (11)	C13—C14—C15—C16	0.0 (2)
C4—C5—C6—C7	1.0 (2)	C17—C14—C15—C16	−179.92 (12)
C5—C6—C7—C2	0.2 (2)	C14—C15—C16—C11	−0.42 (19)
C3—C2—C7—C6	−1.1 (2)	O3—C11—C16—C15	179.37 (12)
C1—C2—C7—C6	178.04 (12)	C12—C11—C16—C15	0.29 (19)
C5—O2—C8—C9	−178.76 (10)	C15—C14—C17—O4	−3.7 (2)
O2—C8—C9—C10	70.22 (13)	C13—C14—C17—O4	176.44 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2ⁱ	0.95	2.57	3.508 (2)	168
C16—H16···O1ⁱⁱ	0.95	2.41	3.287 (2)	154

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₆O₄
M_r	284.30
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	15.3323 (15), 4.6173 (5), 20.2800 (19)
β (°)	104.783 (1)
V (Å³)	1388.2 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.25 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART APEXII diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8297, 3113, 2538
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.106, 1.03
No. of reflections	3113
No. of parameters	190
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.22

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O1ⁱ	0.95	2.41	3.287 (2)	154

Symmetry code: (i) −x+1, −y+2, −z+1.

Acknowledgements

The authors thank the University of Karachi and the University of Malaya for supporting this study.

References

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