4,4'-(Propane-1,3-diyldi-oxy)dibenz-aldehyde.

The title compound, C(17)H(16)O(4), is a dialdehyde in which two formyl-phen-oxy units are linked by a -CH(2)CH(2)CH(2)- chain; the mol-ecule is V-shaped with the middle methyl-ene C atom as the apex. The two benzene rings are aligned at 77.4 (1)°. In the crystal, mol-ecules 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 = 284.30

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.106

S = 1.03

3113 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.22 e Å−3

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 ▶).

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

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

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

C17H16O4	F(000) = 600
Mr = 284.30	Dx = 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

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

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 = 1.02	w = 1/[σ2(Fo2) + (0.0513P)2 + 0.4617P] where P = (Fo2 + 2Fc2)/3
3113 reflections	(Δ/σ)max = 0.001
190 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) .