1,1′-Bicyclo­propyl-1,1′-diyl 1,1′-biphenyl-2,2′-dicarboxyl­ate

Hoong-Kun Fun; Ching Kheng Quah; Kai Xu

doi:10.1107/S160053681201851X

. 2012 May 5;68(Pt 6):o1630. doi: 10.1107/S160053681201851X

1,1′-Bicyclopropyl-1,1′-diyl 1,1′-biphenyl-2,2′-dicarboxylate

Hoong-Kun Fun ^a,^*,^‡, Ching Kheng Quah ^a,^§, Kai Xu ^b

PMCID: PMC3379235 PMID: 22719433

Abstract

In the title compound, C₂₀H₁₆O₄, the two benzene rings form a dihedral angle of 45.70 (4)°. In the crystal, molecules are linked via C—H⋯O interactions into layers lying parallel to the bc plane.

Related literature

For the background to this study, see the first paper in this series: Fun, Quah, Wu & Zhang (2012 ▶). For related structures in this series, see: Fun, Lim, Quah & Wu (2012 ▶); Fun, Quah & Wu (2012 ▶). For standard bond-length data, see: Allen et al. (1987 ▶). For the preparation, see: Wu et al. (2012 ▶). graphic file with name e-68-o1630-scheme1.jpg

Experimental

Crystal data

C₂₀H₁₆O₄
M _r = 320.33
Monoclinic,
a = 26.3197 (14) Å
b = 9.4184 (5) Å
c = 13.3606 (7) Å
β = 100.092 (1)°
V = 3260.7 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.43 × 0.34 × 0.17 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.962, T _max = 0.985
12233 measured reflections
5234 independent reflections
3687 reflections with I > 2σ(I)
R _int = 0.019

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.124
S = 1.04
5234 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681201851X/is5125sup1.cif

e-68-o1630-sup1.cif^{(26.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681201851X/is5125Isup2.hkl

e-68-o1630-Isup2.hkl^{(256.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681201851X/is5125Isup3.cml

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
C3—H3A⋯O3ⁱ	0.93	2.50	3.3410 (16)	151
C4—H4A⋯O3ⁱⁱ	0.93	2.52	3.4104 (15)	161
C10—H10A⋯O1ⁱⁱⁱ	0.93	2.57	3.496 (2)	174

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

Acknowledgments

HKF and CKQ thank Universiti Sains Malaysia for the Research University Grant (No. 1001/PFIZIK/811160). Financial support from the National Natural Science Foundation of China (20972067) is acknowledged.

supplementary crystallographic information

Comment

The title compound was firstly reported as a cyclopropyl ring-fused ten-membered bislactone whose preparation could be achieved through a concise photochemical method (Wu et al., 2012). In the title compound, Fig. 1, the benzene rings (C1–C6 and C7–C12) form a dihedral angle of 45.70 (4)°. Bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to related structures (Fun, Quah, Wu & Zhang, 2012; Fun, Lim, Quah & Wu, 2012; Fun, Quah & Wu, 2012). In the crystal (Fig. 2), molecules are linked via intermolecular C3—H3A···O3, C4—H4A···O3 and C10—H10A···O1 interactions (Table 1) into a layer parallel to the (100) plane.

Experimental

The title compound was derived from the photo-induced sequential reactions of 9,10-phenanthrenedione with bicyclopropylendiene. The compound was purified by flash column chromatography with ethyl acetate/petroleum ether (1:10) as eluents. X-ray quality crystals of the title compound (m.p. 192–194 °C) were obtained from slow evaporation of an acetone and petroleum ether solution (1:10).