2 Ethyl 5 tri­phenyl­methyl 1,3 dioxane

2-Ethyl-5-triphenylmethyl-1,3-dioxane

Lin Yuan,aJiang-Hua Shi,aMin Zhangaand Seik Weng Ngb*

a

Department of Biology and Chemistry, Hunan University of Science and Engineering, Yongzhou Hunan 425100, People’s Republic of China, and

b_{Department of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia}

Correspondence e-mail: [email protected]

Received 9 September 2010; accepted 14 September 2010

Key indicators: single-crystal X-ray study;T= 110 K; mean(C–C) = 0.002 A˚; Rfactor = 0.042;wRfactor = 0.114; data-to-parameter ratio = 17.1.

In the title compound, C25H26O2, the dioxane ring adopts a chair conformation with the two substituent groups occupying equatorial positions.

Related literature

For the crystal structure of 2,2-dimethyl-5-triphenyl-1,3-dioxane, see: Zhanget al.(2009).

Experimental

Crystal data

C25H26O2 Mr= 358.46

Monoclinic,P21=c a= 10.5401 (6) A˚

b= 13.3550 (8) A˚

c= 14.6044 (8) A˚ = 110.523 (1)

V= 1925.28 (19) A˚3

Z= 4

MoKradiation = 0.08 mm 1

T= 110 K

0.450.350.15 mm

Data collection

Bruker SMART APEX diffractometer 9493 measured reflections

4174 independent reflections 3047 reflections withI> 2(I)

Rint= 0.031

Refinement

R[F2_{> 2(F}2_{)] = 0.042} wR(F2_{) = 0.114} S= 1.04 4174 reflections

244 parameters

H-atom parameters constrained

max= 0.29 e A˚ 3

min= 0.19 e A˚ 3

Data collection:SMART(Bruker, 2003); cell refinement:SAINT (Bruker, 2003); 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).

We thank the Key Subject Construction Project of Hunan Province (No. 2006–180), the Key Scientific Research Project of Hunan Provincial Education Department (No. 08 A023, 05 C736), the NSF of Hunan Province (09 J J3028) and the University of Malaya for supporting this study.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZS2066).

References

Barbour, L. J. (2001).J. Supramol. Chem.1, 189–191.

Bruker (2003).SAINTandSMART. Bruker AXS Inc., Madison, Wisconsin, USA.

Sheldrick, G. M. (2008).Acta Cryst.A64, 112–122. Westrip, S. P. (2010).J. Appl. Cryst.43, 920–925.

Zhang, M., Yuan, X.-Y. & Liu, X.-M. (2009).Acta Cryst.E65, o304. Acta Crystallographica Section E

Structure Reports

Online

supporting information

Acta Cryst. (2010). E66, o2582 [doi:10.1107/S1600536810036767]

2-Ethyl-5-triphenylmethyl-1,3-dioxane

Lin Yuan, Jiang-Hua Shi, Min Zhang and Seik Weng Ng

S1. Comment

A previous study reported the crystal structure of 2,2-dimethyl-5-triphenylmethyl-1,3-dioxane (Zhang et al., 2009). Such

disubstituted 1,3-dioxanes are known from NMR studies to have substituents in equatorial rather than in axial

orientations on the six-membered ring. The the title compound, 2-ethyl-5-triphenylmethyl-1,3-dioxane analog (Scheme I,

Fig. 1), has similar features for the dioxane part, which adopts a chair conformation. The substitutent groups occupy

equatorial positions.

S2. Experimental

2-Triphenylmethyl-1,3-propanediol (0.24 g, 5.0 mmol), propionaldehyde (20 mmol) and p-toluenesulfonic acid (0.1 g)

were stirred in dichloromethane (20 ml) for a week. The solvent was evaporated and the residue was dissolved in ether

(20 ml) after which the solution was washed with water and 5% sodium bicarbonate (20 ml). The organic phase was dried

with anhydrous sodium sulfate. The solvent was evaporated and the product was recrystallized from ethyl acetate to give

1.0 g (yield 60%) of colorless crystals.

S3. Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H = 0.95–0.99 Å) and were included in the refinement in

Figure 1

Thermal ellipsoid plot (Barbour, 2001) of the title compound at the 70% probability level.

2-Ethyl-5-triphenylmethyl-1,3-dioxane

Crystal data

C25H26O2 Mr = 358.46 Monoclinic, P21/c

Hall symbol: -P 2ybc

a = 10.5401 (6) Å

b = 13.3550 (8) Å

c = 14.6044 (8) Å

β = 110.523 (1)°

V = 1925.28 (19) Å3 Z = 4

F(000) = 768

Dx = 1.237 Mg m−3

Mo Kα radiation, λ = 0.71073 Å Cell parameters from 3994 reflections

θ = 2.6–27.0°

µ = 0.08 mm−1 T = 110 K Block, colorless 0.45 × 0.35 × 0.15 mm

Data collection

Bruker SMART APEX diffractometer

Radiation source: fine-focus sealed tube Graphite monochromator

ω scans

9493 measured reflections 4174 independent reflections

3047 reflections with I > 2σ(I)

Rint = 0.031

θmax = 27.1°, θmin = 2.1° h = −9→13

k = −17→12

Refinement

Refinement on F2

Least-squares matrix: full

R[F2 _{> 2σ(F}2_{)] = 0.042} wR(F2_{) = 0.114} S = 1.04 4174 reflections 244 parameters 0 restraints

Primary atom site location: structure-invariant direct methods

Secondary atom site location: difference Fourier map

Hydrogen site location: inferred from neighbouring sites

H-atom parameters constrained

w = 1/[σ2_(F

o2) + (0.0568P)2 + 0.2859P]

where P = (Fo2 + 2Fc2)/3

(Δ/σ)max = 0.001

Δρmax = 0.29 e Å−3

Δρmin = −0.19 e Å−3

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

x y z Uiso*/Ueq

H18 0.4921 0.5253 0.3473 0.022* C19 0.64436 (13) 0.38587 (10) 0.29220 (9) 0.0162 (3) C20 0.48869 (13) 0.37838 (10) 0.23326 (9) 0.0163 (3) H20 0.4528 0.4483 0.2205 0.020* C21 0.45229 (13) 0.32618 (11) 0.13438 (10) 0.0191 (3) H21A 0.4950 0.3620 0.0933 0.023* H21B 0.4876 0.2568 0.1440 0.023* C22 0.41008 (13) 0.32455 (11) 0.28894 (10) 0.0186 (3) H22A 0.4418 0.2545 0.3020 0.022* H22B 0.4263 0.3582 0.3525 0.022* C23 0.24357 (14) 0.27454 (11) 0.14269 (9) 0.0178 (3) H23A 0.2791 0.2046 0.1563 0.021* C24 0.09327 (14) 0.27184 (11) 0.08743 (10) 0.0207 (3) H24A 0.0758 0.2405 0.0227 0.025* H24B 0.0578 0.3412 0.0765 0.025* C25 0.01923 (15) 0.21322 (12) 0.14283 (11) 0.0261 (3) H25A −0.0782 0.2131 0.1051 0.039* H25B 0.0354 0.2447 0.2066 0.039* H25C 0.0528 0.1442 0.1525 0.039*

Atomic displacement parameters (Å2₎

U11 _U22 _U33 _U12 _U13 _U23

C24 0.0198 (7) 0.0196 (7) 0.0204 (7) −0.0001 (6) 0.0042 (6) −0.0022 (6) C25 0.0193 (7) 0.0286 (8) 0.0286 (8) −0.0044 (6) 0.0064 (6) −0.0006 (7)

Geometric parameters (Å, º)

O1—C23 1.4125 (16) C13—C18 1.3899 (19) O1—C21 1.4345 (15) C13—C14 1.3994 (19) O2—C23 1.4181 (15) C13—C19 1.5509 (18) O2—C22 1.4355 (15) C14—C15 1.382 (2) C1—C6 1.3959 (19) C14—H14 0.9500 C1—C2 1.403 (2) C15—C16 1.385 (2) C1—C19 1.5465 (19) C15—H15 0.9500 C2—C3 1.387 (2) C16—C17 1.384 (2) C2—H2 0.9500 C16—H16 0.9500 C3—C4 1.387 (2) C17—C18 1.3925 (19) C3—H3 0.9500 C17—H17 0.9500 C4—C5 1.381 (2) C18—H18 0.9500 C4—H4 0.9500 C19—C20 1.5661 (18) C5—C6 1.387 (2) C20—C21 1.5264 (18) C5—H5 0.9500 C20—C22 1.5287 (19) C6—H6 0.9500 C20—H20 1.0000 C7—C8 1.395 (2) C21—H21A 0.9900 C7—C12 1.395 (2) C21—H21B 0.9900 C7—C19 1.5459 (19) C22—H22A 0.9900 C8—C9 1.396 (2) C22—H22B 0.9900 C8—H8 0.9500 C23—C24 1.5053 (18) C9—C10 1.381 (3) C23—H23A 1.0000 C9—H9 0.9500 C24—C25 1.523 (2) C10—C11 1.376 (2) C24—H24A 0.9900 C10—H10 0.9500 C24—H24B 0.9900 C11—C12 1.392 (2) C25—H25A 0.9800 C11—H11 0.9500 C25—H25B 0.9800 C12—H12 0.9500 C25—H25C 0.9800

C4—C5—C6 120.53 (14) C21—C20—C19 114.62 (11) C4—C5—H5 119.7 C22—C20—C19 113.35 (10) C6—C5—H5 119.7 C21—C20—H20 107.3 C5—C6—C1 121.34 (14) C22—C20—H20 107.3 C5—C6—H6 119.3 C19—C20—H20 107.3 C1—C6—H6 119.3 O1—C21—C20 110.30 (11) C8—C7—C12 117.57 (14) O1—C21—H21A 109.6 C8—C7—C19 121.37 (13) C20—C21—H21A 109.6 C12—C7—C19 120.78 (13) O1—C21—H21B 109.6 C7—C8—C9 120.98 (15) C20—C21—H21B 109.6 C7—C8—H8 119.5 H21A—C21—H21B 108.1 C9—C8—H8 119.5 O2—C22—C20 109.71 (10) C10—C9—C8 120.36 (16) O2—C22—H22A 109.7 C10—C9—H9 119.8 C20—C22—H22A 109.7 C8—C9—H9 119.8 O2—C22—H22B 109.7 C11—C10—C9 119.42 (15) C20—C22—H22B 109.7 C11—C10—H10 120.3 H22A—C22—H22B 108.2 C9—C10—H10 120.3 O1—C23—O2 110.18 (10) C10—C11—C12 120.42 (16) O1—C23—C24 109.22 (11) C10—C11—H11 119.8 O2—C23—C24 108.81 (11) C12—C11—H11 119.8 O1—C23—H23A 109.5 C11—C12—C7 121.26 (15) O2—C23—H23A 109.5 C11—C12—H12 119.4 C24—C23—H23A 109.5 C7—C12—H12 119.4 C23—C24—C25 111.50 (11) C18—C13—C14 117.58 (12) C23—C24—H24A 109.3 C18—C13—C19 123.54 (12) C25—C24—H24A 109.3 C14—C13—C19 118.71 (12) C23—C24—H24B 109.3 C15—C14—C13 121.43 (13) C25—C24—H24B 109.3 C15—C14—H14 119.3 H24A—C24—H24B 108.0 C13—C14—H14 119.3 C24—C25—H25A 109.5 C14—C15—C16 120.50 (13) C24—C25—H25B 109.5 C14—C15—H15 119.8 H25A—C25—H25B 109.5 C16—C15—H15 119.8 C24—C25—H25C 109.5 C17—C16—C15 118.78 (13) H25A—C25—H25C 109.5 C17—C16—H16 120.6 H25B—C25—H25C 109.5