1-(4-Meth­oxy­phen­yl)ethane-1,2-diyl 1,1′-biphenyl-2,2′-dicarboxyl­ate

Hoong-Kun Fun; Ching Kheng Quah; Dongdong Wu

doi:10.1107/S160053681201848X

. 2012 May 5;68(Pt 6):o1628. doi: 10.1107/S160053681201848X

1-(4-Methoxyphenyl)ethane-1,2-diyl 1,1′-biphenyl-2,2′-dicarboxylate

Hoong-Kun Fun ^a,^*,^‡, Ching Kheng Quah ^a,^§, Dongdong Wu ^b

PMCID: PMC3379233 PMID: 22719431

Abstract

In the title molecule, C₂₃H₁₈O₅, the methoxy-substituted benzene ring makes dihedral angles of 65.12 (4) and 88.55 (4)° with the other two benzene rings. These two benzene rings form a dihedral angle of 45.70 (4)°. In the crystal, molecules are linked into inversion dimers by pairs of weak C—H⋯O hydrogen bonds.

Related literature

For the background to this study has been set out in the preceding paper, see: Fun et al. (2012 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶). For standard bond-length data, see: Allen et al. (1987 ▶). For the preparation, see: Wu et al. (2012 ▶). graphic file with name e-68-o1628-scheme1.jpg

Experimental

Crystal data

C₂₃H₁₈O₅
M _r = 374.37
Monoclinic,
a = 14.0049 (5) Å
b = 10.8637 (4) Å
c = 12.7190 (5) Å
β = 110.150 (1)°
V = 1816.69 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.50 × 0.37 × 0.33 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.954, T _max = 0.969
30595 measured reflections
8040 independent reflections
6872 reflections with I > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.122
S = 1.03
8040 reflections
254 parameters
H-atom parameters constrained
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.23 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/S160053681201848X/is5123sup1.cif

e-68-o1628-sup1.cif^{(27.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681201848X/is5123Isup2.hkl

e-68-o1628-Isup2.hkl^{(393.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681201848X/is5123Isup3.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
C16—H16A⋯O3ⁱ	0.98	2.60	3.2676 (10)	126

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Symmetry code: (i) Inline graphic .

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 belongs to the biphenyl-containing bislactone family whose preparation could be achieved through a concise photochemical method (Wu et al., 2012). In the title compound, Fig. 1, the methoxy attached phenyl ring (C17–C22) inclines at dihedral angles of 65.12 (4) and 88.55 (4)° with the two benzene rings (C2–C7 and C8–C13), respectively. The two benzene rings form a dihedral angle of 45.70 (4)°. Bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to a related structure (Fun et al., 2012). In the crystal (Fig. 2), molecules are linked into inversion dimers by pairs of intermolecular C16—H16A···O3 hydrogen bonds (Table 1).

Experimental

The title compound was the major diastereoisomer of the sequential photoreaction products of 9,10-phenanthrenedione with 1-methoxy-4-vinylbenzene. The compound was purified by flash column chromatography with ethyl acetate/petroleum ether (1:9) as eluents. X-ray quality crystals of the title compound were obtained from slow evaporation of an acetone and petroleum ether solution (1:10).