trans-1,2,3-Tris(4-methoxy­benzo­yl)cyclo­propane

Jingjing Sun; Nengfang She

doi:10.1107/S1600536809005145

. 2009 Feb 25;65(Pt 3):o588. doi: 10.1107/S1600536809005145

trans-1,2,3-Tris(4-methoxybenzoyl)cyclopropane

Jingjing Sun ^a,^*, Nengfang She ^a

PMCID: PMC2968624 PMID: 21582243

Abstract

In the title compound, C₂₇H₂₄O₆, the packing of the molecules is mainly governed by C—H⋯O interactions.

Related literature

For related structures, see: Saba (1990 ▶). For background to the chemistry of cyclopropanes as a versatile tool in organic synthesis, see: Wong (1989 ▶).

Experimental

Crystal data

C₂₇H₂₄O₆
M _r = 444.46
Triclinic,
a = 10.1897 (6) Å
b = 10.626 (6) Å
c = 10.6931 (6) Å
α = 90.736 (1)°
β = 103.194 (1)°
γ = 92.432 (1)°
V = 1125.9 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.30 × 0.20 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
9852 measured reflections
4349 independent reflections
2862 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.057
wR(F ²) = 0.155
S = 1.06
4349 reflections
301 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809005145/rk2123sup1.cif

e-65-0o588-sup1.cif^{(23.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809005145/rk2123Isup2.hkl

e-65-0o588-Isup2.hkl^{(213.1KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C26—H26⋯O2ⁱ	0.93	2.54	3.467 (3)	175
C11—H11⋯O6ⁱⁱ	0.98	2.51	3.270 (3)	134
C7—H7⋯O5ⁱⁱⁱ	0.93	2.52	3.171 (3)	128
C9—H9⋯O3ⁱⁱⁱ	0.98	2.55	3.497 (3)	164
C27—H27B⋯O4^iv	0.96	2.58	3.136 (3)	117

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) .

Acknowledgments

The authors thank Professor An–Xin Wu for technical assistance and Dr Xiang–Gao Meng for the data collection.

supplementary crystallographic information

Comment

The unusual bonding of cyclopropanes and the strain release associated with cleavage of cyclopropanes offer the possibility of recognizing that structural unit when it is a part of a larger molecule. We report here the molecular structure of the title cyclopropane derivative (Fig. 1), which is an important intermediate in organic synthesis (Saba, 1990). Since numerous methodologies have been developed for the construction of three–membered carbocycles, the chemistry of cyclopropanes has emerged as a versatile tool in organic synthesis (Wong, 1989).

The crystal packing is stabilized by intermolecular C—H···O interaction.

Experimental

The title compound was synthesized according to the procedure reported (Saba, 1990). Crystals appropriate for X–ray data collection were obtained by slow evaporation of the dichloromethane solution at 293 K.