(2E)-3-(3-Bromo-4-meth­oxy­phen­yl)-1-(4,4′′-difluoro-5′-meth­oxy-1,1′:3′,1′′-terphenyl-4′-yl)prop-2-en-1-one

Hoong-Kun Fun; Tara Shahani; S Samshuddin; B Narayana; B K Sarojini

doi:10.1107/S1600536811050884

. 2011 Nov 30;67(Pt 12):o3514. doi: 10.1107/S1600536811050884

(2E)-3-(3-Bromo-4-methoxyphenyl)-1-(4,4′′-difluoro-5′-methoxy-1,1′:3′,1′′-terphenyl-4′-yl)prop-2-en-1-one

Hoong-Kun Fun ^a,^*,^‡, Tara Shahani ^a, S Samshuddin ^b, B Narayana ^b, B K Sarojini ^c

PMCID: PMC3239135 PMID: 22199983

Abstract

In the title compound, C₂₉H₂₁BrF₂O₃, the dihedral angles between the central anisole ring and the pendant fluorobenzene rings are 48.86 (19) and 31.89 (18)°. The dihedral angle between the anisole ring and the 1-bromo-2-methoxybenzene ring linked via the enone bridge is 82.95 (17)°. In the crystal, C—H⋯O hydrogen bonds link the molecules into C(11) chains propagating along [010].

Related literature

For related structures and background to chalcones and their properties, see: Fun et al. (2010a ▶,b ▶).

Experimental

Crystal data

C₂₉H₂₁BrF₂O₃
M _r = 535.37
Monoclinic,
a = 9.6902 (6) Å
b = 20.3345 (12) Å
c = 12.9556 (8) Å
β = 110.636 (1)°
V = 2389.0 (3) Å³
Z = 4
Mo Kα radiation
μ = 1.77 mm⁻¹
T = 296 K
0.42 × 0.15 × 0.10 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) ▶ T _min = 0.525, T _max = 0.843
22747 measured reflections
5455 independent reflections
4111 reflections with I > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.056
wR(F ²) = 0.183
S = 1.04
5455 reflections
318 parameters
H-atom parameters constrained
Δρ_max = 1.96 e Å⁻³
Δρ_min = −0.39 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/S1600536811050884/hb6536sup1.cif

e-67-o3514-sup1.cif^{(23.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811050884/hb6536Isup2.hkl

e-67-o3514-Isup2.hkl^{(267.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811050884/hb6536Isup3.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
C29—H29B⋯O2ⁱ	0.96	2.41	3.303 (6)	155

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Symmetry code: (i) Inline graphic .

Acknowledgments

HKF and TSH thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). TSH also thanks USM for the award of a research fellowship. BN thanks the UGC for financial assistance through the SAP and BSR one-time grant for the purchase of chemicals. SS thanks Mangalore University for research facilities.

supplementary crystallographic information

Comment

As part of our ongoing studies of substituted chalcone derivatives, (Fun et al., 2010a,b), the title compound (I) was prepared and its crystal structure is reported. The precursor of the title compound was prepared from 4,4'-difluoro chalcone by several steps.

The title molecule is built up (Fig. 1) from four units, namely: two fluorobenzenes (C1–C6/F1) and (C13–C18/F2), a anisole (C7–C12/O1/C28) and a 1-bromo-2- methoxybenzene (C22/C27/Br1/C29/O3). The anisole moiety makes dihedral angles of 48.86 (19)°, 31.89 (18)° and 82.95 (17)° with the two fluorobenzenes and 1-bromo-2-methoxybenzene moieties respectively.

In the crystal (Fig. 2), C29—H29B···O2 hydrogen bonds link the molecules into chains along [010].

Experimental

To a mixture of 1-(4,4''-difluoro-5'-methoxy-1,1':3',1''-terphenyl-4'-yl) ethanone (0.338 g, 0.001 mol) and 3-bromo-4-methoxybenzaldehyde (0.215 g, 0.001 mol) in 30 ml e thanol, 0.5 ml of 10% sodium hydroxide solution was added and stirred at 5–10 °C for 3 h. The precipitate formed was collected by filtration and purified by recrystallization from ethanol. Colourless blocks of (I) were grown from DMF by slow evaporation and the yield of the compound was 82%. Mp: 452 K.