Diethyl 4,4′-[(1,3-dioxolane-2,2-di­yl)bis­(propyl­idene­oxy)]dibenzoate

Zhang, L.-P.; Jia, Z.-F.; Wei, G.-H.; Liu, Y.-Y.

doi:10.1107/S1600536807057200

Diethyl 4,4'-[(1,3-dioxolane-2,2-diyl)bis(propylideneoxy)]dibenzoate

L.-P. Zhang, Z.-F. Jia, G.-H. Wei and Y.-Y. Liu

The title ester, C₂₇H₃₄O₈, was synthesized by reacting 1,7-dichloro-4-oxoheptane, sodium hydroxide and ethyl p-hydroxybenzoate at 333 K in dimethyl sulfoxide. The 1,3-dioxolane ring is planar [largest deviation from the mean plane = 0.080 (1) Å] and makes dihedral angles of 59.83 (6) and 86.01 (6)° with the benzene rings. The angle between the mean planes of the two benzene rings is 36.05 (8)°.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807057200/dn2261sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807057200/dn2261Isup2.hkl Contains datablock I

CCDC reference: 672915

checkCIF report

Key indicators

Single-crystal X-ray study
T = 273 K
Mean (C-C) = 0.002 Å
R factor = 0.047
wR factor = 0.138
Data-to-parameter ratio = 19.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.96

Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.81 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.18 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C14
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C26    -   C27    ...       1.40 Ang.

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Dicarboxylic ester is a precursor for the synthesis

of dicarboxylate found as bridging ligand. In this

paper, the structure of the title compound, (I), is

described.

In the title compound (I), the 1,3-dioxolane is planar with the largest deviation from the mean plane being 0.080 (1) Å. It makes dihedral angles of 59.83 (6)° and 86.01 (6) respectively with the benzene rings (Fig. 1). The angle between the mean planes of the two benzene rings is 36.05 (8)°.

Both the C3—O1 (1.203 (2) Å) and the C25—O7 (1.197 (2) Å) distances are similar to those of coordinated ester molecules (Gonzàlez-Duarte et al., 1996; Ríos-Moreno et al., 2003). The C3—O2 and the C25—O8 distances are shorter than that of the reported ester molecule (Ping et al., 2007). The O1—C3—O2 and O7—C25—O8 angles are 122.7 (2)° and 123.3 (2)° respectively.

Related literature top

For related literature, see: Gonzàlez-Duarte, March & Pons (1996); Ping et al. (2007); Ríos-Moreno, Aguirre, Parra-Hake & Walsh (2003).

Experimental top

To a solution of 1,7-dichloro-4-oxoheptane (5.3 g, 3.0 mmol) and ethylene glycol (1.9 g, 3.0 mmol) in cyclohexane (22.5 ml) was added 0.015 g sodium bisulfate. The reaction mixture was refluxed for 3 h with azeotropic removal of water via a Dean–Stark trap, until there was no water created. The resulting clear solution was cooled down, washed with water twice, and then distilled. Collected the distillation between 447 K and 453 K.

A mixture of ethyl p-hydroxybenzoate (8.3 g, 50 mmol) and NaOH (2.0 g, 50 mmol) in DMSO (10 ml) was stirred at 333 K for 1 h, and then the collected distillation (5.5 g, 25 mmol) in the last step was added. The mixture was cooled to room temperature after stirring at 333 K for 2 h, then poured into 200 ml of water and a white solid formed immediately. The obtained precipitate (0.20 g) was dissolved in 15 ml me thanol, and colorless single crystals of (I) were obtained after several days at room temperature.

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures top

Fig. 1. Molecular view of (I) with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as smal spheres of arbitrary radii.

Diethyl 4,4'-[(1,3-dioxolane-2,2-diyl)bis(propylideneoxy)]dibenzoate top

Crystal data top

C₂₇H₃₄O₈	F(000) = 1040
M_r = 486.54	D_x = 1.259 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6146 reflections
a = 20.445 (3) Å	θ = 2.1–28.4°
b = 7.1533 (9) Å	µ = 0.09 mm⁻¹
c = 18.828 (3) Å	T = 273 K
β = 111.178 (2)°	Block, colorless
V = 2567.6 (6) Å³	0.40 × 0.30 × 0.25 mm
Z = 4

Data collection top

Bruker APEX CCD area-detector diffractometer	6146 independent reflections
Radiation source: fine-focus sealed tube	4195 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω scans	θ_max = 28.4°, θ_min = 2.1°
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	h = −26→22
T_min = 0.970, T_max = 0.980	k = −7→9
15083 measured reflections	l = −23→24

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.138	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0642P)² + 0.323P] where P = (F_o² + 2F_c²)/3
6146 reflections	(Δ/σ)_max < 0.001
318 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₂₇H₃₄O₈	V = 2567.6 (6) Å³
M_r = 486.54	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 20.445 (3) Å	µ = 0.09 mm⁻¹
b = 7.1533 (9) Å	T = 273 K
c = 18.828 (3) Å	0.40 × 0.30 × 0.25 mm
β = 111.178 (2)°

Data collection top

Bruker APEX CCD area-detector diffractometer	6146 independent reflections
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	4195 reflections with I > 2σ(I)
T_min = 0.970, T_max = 0.980	R_int = 0.027
15083 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.138	H-atom parameters constrained
S = 1.04	Δρ_max = 0.21 e Å⁻³
6146 reflections	Δρ_min = −0.20 e Å⁻³
318 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
C1	0.02684 (12)	−0.3465 (3)	0.84609 (13)	0.0823 (6)
H1A	0.0708	−0.3324	0.8876	0.123*
H1B	−0.0016	−0.4364	0.8596	0.123*
H1C	0.0030	−0.2284	0.8355	0.123*
C2	0.03974 (11)	−0.4122 (3)	0.77711 (12)	0.0746 (5)
H2A	0.0619	−0.5343	0.7864	0.090*
H2B	−0.0043	−0.4223	0.7343	0.090*
C3	0.10844 (9)	−0.3230 (2)	0.70460 (10)	0.0607 (4)
C4	0.15387 (8)	−0.1780 (2)	0.69055 (9)	0.0518 (4)
C5	0.17838 (9)	−0.2043 (2)	0.63103 (10)	0.0586 (4)
H5	0.1656	−0.3113	0.6012	0.070*
C6	0.22105 (9)	−0.0743 (2)	0.61594 (9)	0.0577 (4)
H6	0.2371	−0.0938	0.5762	0.069*
C7	0.24012 (8)	0.0860 (2)	0.66001 (8)	0.0490 (3)
C8	0.21656 (8)	0.1141 (2)	0.72001 (9)	0.0534 (4)
H8	0.2297	0.2209	0.7501	0.064*
C9	0.17343 (8)	−0.0179 (2)	0.73460 (9)	0.0534 (4)
H9	0.1574	0.0011	0.7744	0.064*
C10	0.30664 (9)	0.3697 (2)	0.68653 (10)	0.0552 (4)
H10A	0.3370	0.3332	0.7374	0.066*
H10B	0.2674	0.4396	0.6905	0.066*
C11	0.34663 (8)	0.4888 (2)	0.64991 (9)	0.0525 (4)
H11A	0.3615	0.6027	0.6793	0.063*
H11B	0.3154	0.5238	0.5992	0.063*
C12	0.41081 (7)	0.3922 (2)	0.64395 (8)	0.0462 (3)
H12A	0.4380	0.3384	0.6931	0.055*
H12B	0.3954	0.2906	0.6076	0.055*
C13	0.45780 (7)	0.52163 (19)	0.61951 (7)	0.0414 (3)
C14	0.42956 (14)	0.8031 (3)	0.55640 (12)	0.0881 (7)
H14A	0.3858	0.8718	0.5365	0.106*
H14B	0.4590	0.8399	0.5283	0.106*
C15	0.46497 (11)	0.8422 (2)	0.63740 (10)	0.0681 (5)
H15A	0.5066	0.9171	0.6457	0.082*
H15B	0.4340	0.9098	0.6571	0.082*
C16	0.51950 (7)	0.4206 (2)	0.60861 (8)	0.0464 (3)
H16A	0.5020	0.3088	0.5786	0.056*
H16B	0.5389	0.5011	0.5797	0.056*
C17	0.57797 (8)	0.3653 (2)	0.68199 (8)	0.0509 (4)
H17A	0.5929	0.4749	0.7141	0.061*
H17B	0.5599	0.2753	0.7088	0.061*
C18	0.64087 (8)	0.2817 (2)	0.66954 (9)	0.0521 (4)
H18A	0.6545	0.3597	0.6350	0.063*
H18B	0.6802	0.2741	0.7176	0.063*
C19	0.67059 (7)	0.0015 (2)	0.61767 (8)	0.0454 (3)
C20	0.65193 (8)	−0.1792 (2)	0.59131 (9)	0.0543 (4)
H20	0.6090	−0.2270	0.5891	0.065*
C21	0.69578 (8)	−0.2883 (2)	0.56840 (9)	0.0537 (4)
H21	0.6823	−0.4090	0.5508	0.064*
C22	0.76018 (8)	−0.2196 (2)	0.57126 (8)	0.0511 (4)
C23	0.77802 (8)	−0.0381 (2)	0.59612 (10)	0.0610 (4)
H23	0.8204	0.0107	0.5967	0.073*
C24	0.73444 (8)	0.0730 (2)	0.62020 (10)	0.0569 (4)
H24	0.7478	0.1938	0.6378	0.068*
C25	0.80624 (9)	−0.3425 (3)	0.54606 (10)	0.0633 (4)
C26	0.90744 (14)	−0.3554 (3)	0.51253 (19)	0.1142 (10)
H26A	0.9328	−0.4491	0.5495	0.137*
H26B	0.8797	−0.4190	0.4659	0.137*
C27	0.95507 (16)	−0.2345 (4)	0.49826 (19)	0.1164 (9)
H27A	0.9298	−0.1401	0.4626	0.175*
H27B	0.9840	−0.3041	0.4774	0.175*
H27C	0.9840	−0.1763	0.5450	0.175*
O1	0.09351 (9)	−0.4681 (2)	0.67015 (9)	0.1014 (5)
O2	0.08523 (6)	−0.27723 (16)	0.76033 (7)	0.0661 (3)
O3	0.28179 (6)	0.20775 (16)	0.64019 (6)	0.0605 (3)
O4	0.41679 (5)	0.61061 (14)	0.54943 (5)	0.0524 (3)
O5	0.48317 (5)	0.66843 (14)	0.67395 (5)	0.0501 (3)
O6	0.62232 (5)	0.09811 (14)	0.63770 (6)	0.0526 (3)
O7	0.79521 (8)	−0.50437 (19)	0.53014 (10)	0.0900 (4)
O8	0.86127 (7)	−0.25069 (19)	0.54170 (9)	0.0838 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0864 (14)	0.0771 (13)	0.1029 (15)	0.0097 (11)	0.0576 (12)	0.0188 (11)
C2	0.0739 (11)	0.0675 (11)	0.0927 (14)	−0.0166 (9)	0.0424 (10)	0.0046 (10)
C3	0.0622 (9)	0.0556 (9)	0.0676 (10)	−0.0103 (8)	0.0274 (8)	−0.0040 (8)
C4	0.0486 (8)	0.0490 (8)	0.0586 (9)	−0.0037 (7)	0.0201 (7)	−0.0008 (7)
C5	0.0665 (10)	0.0512 (9)	0.0601 (10)	−0.0099 (7)	0.0252 (8)	−0.0129 (7)
C6	0.0660 (10)	0.0589 (9)	0.0555 (9)	−0.0062 (8)	0.0309 (8)	−0.0097 (7)
C7	0.0472 (8)	0.0518 (8)	0.0509 (8)	−0.0057 (6)	0.0211 (6)	−0.0026 (7)
C8	0.0574 (9)	0.0512 (8)	0.0578 (9)	−0.0099 (7)	0.0282 (7)	−0.0109 (7)
C9	0.0537 (8)	0.0534 (9)	0.0601 (9)	−0.0047 (7)	0.0291 (7)	−0.0048 (7)
C10	0.0575 (9)	0.0540 (9)	0.0636 (9)	−0.0105 (7)	0.0336 (8)	−0.0116 (7)
C11	0.0556 (9)	0.0497 (8)	0.0589 (9)	−0.0058 (7)	0.0288 (7)	−0.0044 (7)
C12	0.0499 (8)	0.0450 (8)	0.0472 (8)	−0.0030 (6)	0.0218 (6)	0.0016 (6)
C13	0.0471 (7)	0.0426 (7)	0.0338 (6)	−0.0021 (6)	0.0139 (5)	0.0003 (5)
C14	0.1272 (19)	0.0538 (11)	0.0686 (12)	0.0055 (11)	0.0177 (12)	0.0171 (9)
C15	0.1049 (14)	0.0425 (8)	0.0639 (10)	−0.0050 (9)	0.0390 (10)	0.0012 (7)
C16	0.0520 (8)	0.0498 (8)	0.0432 (7)	−0.0041 (6)	0.0241 (6)	0.0000 (6)
C17	0.0528 (8)	0.0552 (9)	0.0493 (8)	0.0013 (7)	0.0241 (7)	0.0014 (7)
C18	0.0498 (8)	0.0512 (8)	0.0591 (9)	−0.0029 (7)	0.0241 (7)	0.0005 (7)
C19	0.0429 (7)	0.0476 (8)	0.0463 (8)	−0.0009 (6)	0.0170 (6)	0.0048 (6)
C20	0.0496 (8)	0.0513 (8)	0.0639 (9)	−0.0106 (7)	0.0227 (7)	0.0041 (7)
C21	0.0607 (9)	0.0449 (8)	0.0544 (9)	−0.0065 (7)	0.0195 (7)	−0.0006 (7)
C22	0.0515 (8)	0.0535 (8)	0.0484 (8)	−0.0013 (7)	0.0180 (7)	−0.0056 (6)
C23	0.0463 (8)	0.0659 (10)	0.0759 (11)	−0.0128 (8)	0.0282 (8)	−0.0181 (8)
C24	0.0483 (8)	0.0540 (9)	0.0723 (10)	−0.0124 (7)	0.0264 (7)	−0.0167 (8)
C25	0.0612 (10)	0.0609 (10)	0.0694 (11)	−0.0005 (8)	0.0256 (8)	−0.0096 (8)
C26	0.1107 (19)	0.0841 (15)	0.186 (3)	−0.0003 (14)	0.099 (2)	−0.0398 (17)
C27	0.126 (2)	0.1080 (19)	0.157 (3)	0.0088 (16)	0.102 (2)	−0.0145 (18)
O1	0.1405 (14)	0.0758 (9)	0.1170 (12)	−0.0527 (9)	0.0816 (11)	−0.0353 (9)
O2	0.0699 (7)	0.0577 (7)	0.0833 (8)	−0.0126 (6)	0.0429 (7)	−0.0037 (6)
O3	0.0704 (7)	0.0621 (7)	0.0611 (7)	−0.0204 (6)	0.0382 (6)	−0.0136 (5)
O4	0.0580 (6)	0.0573 (6)	0.0379 (5)	−0.0015 (5)	0.0124 (4)	0.0065 (4)
O5	0.0602 (6)	0.0420 (5)	0.0434 (5)	−0.0025 (4)	0.0132 (5)	−0.0037 (4)
O6	0.0459 (5)	0.0482 (6)	0.0698 (7)	−0.0037 (4)	0.0280 (5)	0.0013 (5)
O7	0.0909 (10)	0.0598 (8)	0.1276 (13)	−0.0012 (7)	0.0495 (9)	−0.0207 (8)
O8	0.0768 (8)	0.0726 (8)	0.1228 (12)	−0.0071 (7)	0.0609 (8)	−0.0309 (8)

Geometric parameters (Å, º) top

C1—C2	1.491 (3)	C14—H14A	0.9700
C1—H1A	0.9600	C14—H14B	0.9700
C1—H1B	0.9600	C15—O5	1.4041 (19)
C1—H1C	0.9600	C15—H15A	0.9700
C2—O2	1.452 (2)	C15—H15B	0.9700
C2—H2A	0.9700	C16—C17	1.517 (2)
C2—H2B	0.9700	C16—H16A	0.9700
C3—O1	1.204 (2)	C16—H16B	0.9700
C3—O2	1.339 (2)	C17—C18	1.511 (2)
C3—C4	1.479 (2)	C17—H17A	0.9700
C4—C9	1.385 (2)	C17—H17B	0.9700
C4—C5	1.396 (2)	C18—O6	1.4368 (18)
C5—C6	1.373 (2)	C18—H18A	0.9700
C5—H5	0.9300	C18—H18B	0.9700
C6—C7	1.386 (2)	C19—O6	1.3647 (17)
C6—H6	0.9300	C19—C24	1.387 (2)
C7—O3	1.3613 (17)	C19—C20	1.388 (2)
C7—C8	1.394 (2)	C20—C21	1.371 (2)
C8—C9	1.386 (2)	C20—H20	0.9300
C8—H8	0.9300	C21—C22	1.388 (2)
C9—H9	0.9300	C21—H21	0.9300
C10—O3	1.4289 (18)	C22—C23	1.384 (2)
C10—C11	1.509 (2)	C22—C25	1.486 (2)
C10—H10A	0.9700	C23—C24	1.387 (2)
C10—H10B	0.9700	C23—H23	0.9300
C11—C12	1.523 (2)	C24—H24	0.9300
C11—H11A	0.9700	C25—O7	1.197 (2)
C11—H11B	0.9700	C25—O8	1.331 (2)
C12—C13	1.5204 (18)	C26—C27	1.399 (3)
C12—H12A	0.9700	C26—O8	1.459 (2)
C12—H12B	0.9700	C26—H26A	0.9700
C13—O5	1.4277 (16)	C26—H26B	0.9700
C13—O4	1.4316 (16)	C27—H27A	0.9600
C13—C16	1.5305 (19)	C27—H27B	0.9600
C14—O4	1.399 (2)	C27—H27C	0.9600
C14—C15	1.459 (3)

C2—C1—H1A	109.5	O5—C15—C14	106.64 (14)
C2—C1—H1B	109.5	O5—C15—H15A	110.4
H1A—C1—H1B	109.5	C14—C15—H15A	110.4
C2—C1—H1C	109.5	O5—C15—H15B	110.4
H1A—C1—H1C	109.5	C14—C15—H15B	110.4
H1B—C1—H1C	109.5	H15A—C15—H15B	108.6
O2—C2—C1	107.97 (16)	C17—C16—C13	114.68 (11)
O2—C2—H2A	110.1	C17—C16—H16A	108.6
C1—C2—H2A	110.1	C13—C16—H16A	108.6
O2—C2—H2B	110.1	C17—C16—H16B	108.6
C1—C2—H2B	110.1	C13—C16—H16B	108.6
H2A—C2—H2B	108.4	H16A—C16—H16B	107.6
O1—C3—O2	122.72 (15)	C18—C17—C16	113.37 (12)
O1—C3—C4	124.21 (16)	C18—C17—H17A	108.9
O2—C3—C4	113.07 (14)	C16—C17—H17A	108.9
C9—C4—C5	118.85 (14)	C18—C17—H17B	108.9
C9—C4—C3	122.47 (14)	C16—C17—H17B	108.9
C5—C4—C3	118.68 (14)	H17A—C17—H17B	107.7
C6—C5—C4	120.93 (15)	O6—C18—C17	108.38 (12)
C6—C5—H5	119.5	O6—C18—H18A	110.0
C4—C5—H5	119.5	C17—C18—H18A	110.0
C5—C6—C7	119.91 (14)	O6—C18—H18B	110.0
C5—C6—H6	120.0	C17—C18—H18B	110.0
C7—C6—H6	120.0	H18A—C18—H18B	108.4
O3—C7—C6	115.69 (13)	O6—C19—C24	124.70 (13)
O3—C7—C8	124.32 (13)	O6—C19—C20	115.96 (12)
C6—C7—C8	119.99 (14)	C24—C19—C20	119.32 (14)
C9—C8—C7	119.56 (14)	C21—C20—C19	121.10 (14)
C9—C8—H8	120.2	C21—C20—H20	119.4
C7—C8—H8	120.2	C19—C20—H20	119.4
C4—C9—C8	120.76 (14)	C20—C21—C22	120.34 (14)
C4—C9—H9	119.6	C20—C21—H21	119.8
C8—C9—H9	119.6	C22—C21—H21	119.8
O3—C10—C11	108.09 (12)	C23—C22—C21	118.41 (14)
O3—C10—H10A	110.1	C23—C22—C25	122.90 (14)
C11—C10—H10A	110.1	C21—C22—C25	118.67 (14)
O3—C10—H10B	110.1	C22—C23—C24	121.76 (14)
C11—C10—H10B	110.1	C22—C23—H23	119.1
H10A—C10—H10B	108.4	C24—C23—H23	119.1
C10—C11—C12	113.66 (13)	C23—C24—C19	119.03 (14)
C10—C11—H11A	108.8	C23—C24—H24	120.5
C12—C11—H11A	108.8	C19—C24—H24	120.5
C10—C11—H11B	108.8	O7—C25—O8	123.31 (16)
C12—C11—H11B	108.8	O7—C25—C22	124.65 (16)
H11A—C11—H11B	107.7	O8—C25—C22	112.04 (14)
C13—C12—C11	113.68 (12)	C27—C26—O8	110.2 (2)
C13—C12—H12A	108.8	C27—C26—H26A	109.6
C11—C12—H12A	108.8	O8—C26—H26A	109.6
C13—C12—H12B	108.8	C27—C26—H26B	109.6
C11—C12—H12B	108.8	O8—C26—H26B	109.6
H12A—C12—H12B	107.7	H26A—C26—H26B	108.1
O5—C13—O4	105.94 (10)	C26—C27—H27A	109.5
O5—C13—C12	109.64 (11)	C26—C27—H27B	109.5
O4—C13—C12	109.03 (11)	H27A—C27—H27B	109.5
O5—C13—C16	109.88 (11)	C26—C27—H27C	109.5
O4—C13—C16	108.84 (10)	H27A—C27—H27C	109.5
C12—C13—C16	113.24 (11)	H27B—C27—H27C	109.5
O4—C14—C15	106.96 (14)	C3—O2—C2	116.36 (14)
O4—C14—H14A	110.3	C7—O3—C10	118.10 (11)
C15—C14—H14A	110.3	C14—O4—C13	108.90 (12)
O4—C14—H14B	110.3	C15—O5—C13	109.63 (11)
C15—C14—H14B	110.3	C19—O6—C18	118.04 (11)
H14A—C14—H14B	108.6	C25—O8—C26	116.51 (16)

Experimental details

Crystal data
Chemical formula	C₂₇H₃₄O₈
M_r	486.54
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	273
a, b, c (Å)	20.445 (3), 7.1533 (9), 18.828 (3)
β (°)	111.178 (2)
V (Å³)	2567.6 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.40 × 0.30 × 0.25

Data collection
Diffractometer	Bruker APEX CCD area-detector diffractometer
Absorption correction	Empirical (using intensity measurements) (SADABS; Sheldrick, 1996)
T_min, T_max	0.970, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	15083, 6146, 4195
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.138, 1.04
No. of reflections	6146
No. of parameters	318
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.20

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996); ORTEP-3 for Windows (Farrugia, 1997), SHELXL97.

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Diethyl 4,4'-[(1,3-dioxolane-2,2-di­yl)bis­(propyl­idene­oxy)]dibenzoate

Supporting information

Key indicators

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Diethyl 4,4'-[(1,3-dioxolane-2,2-diyl)bis(propylideneoxy)]dibenzoate