(E)-1-([1,1′-Biphen­yl]-4-yl)-3-(2-methyl­phen­yl)prop-2-en-1-one

D Shanthi; T Vidhya Sagar; M Kayalvizhi; G Vasuki; A Thiruvalluvar

doi:10.1107/S1600536814014317

. 2014 Jun 25;70(Pt 7):o809–o810. doi: 10.1107/S1600536814014317

(E)-1-([1,1′-Biphenyl]-4-yl)-3-(2-methylphenyl)prop-2-en-1-one

D Shanthi ^a, T Vidhya Sagar ^a, M Kayalvizhi ^b, G Vasuki ^b, A Thiruvalluvar ^c,^*

PMCID: PMC4120573 PMID: 25161590

Abstract

In the title molecule, C₂₂H₁₈O, the o-tolyl ring is connected through a conjugated double bond. The molecule adopts an E conformation and the C—C=C—C torsion angle is 178.77 (13)°. The overall conformation may be described by the values of dihedral angles between the different planes. The terminal rings are twisted by an angle of 54.75 (8)°, while the biphenyl part is not planar, the dihedral angle between the planes of the rings being 40.65 (8)°. The dihedral angle between the benzene rings is 14.10 (7)°. There are three weak C—H⋯π interactions found in the crystal structure. No classic hydrogen bonds are observed.

Keywords: crystal structure

Related literature

For the bioactivity of chalcones, see: Dimmock et al. (1999 ▶). For biological applications of chalcones, see: Opletalova (2000 ▶); Opletalova & Sedivy (1999 ▶). For chalcones as non-linear optical materials, see: Fichou et al. (1988 ▶); Goto et al. (1991 ▶). For further applications of chalcones, see: Sarojini et al. (2006 ▶). For the crystal structures of related compounds, see: Betz et al. (2011a ▶,b ▶). For bond-length data, see: Allen et al. (1987 ▶). graphic file with name e-70-0o809-scheme1.jpg

Experimental

Crystal data

C₂₂H₁₈O
M _r = 298.36
Triclinic,
a = 7.6396 (3) Å
b = 9.9106 (4) Å
c = 11.9263 (4) Å
α = 103.166 (2)°
β = 104.713 (2)°
γ = 103.308 (2)°
V = 809.66 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 273 K
0.40 × 0.35 × 0.30 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T _min = 0.908, T _max = 1.000
18636 measured reflections
4534 independent reflections
3291 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.151
S = 1.06
4534 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL2014 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814014317/jj2188sup1.cif

e-70-0o809-sup1.cif^{(19.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814014317/jj2188Isup2.hkl

e-70-0o809-Isup2.hkl^{(248.6KB, hkl)}

Click here for additional data file.^{(2.5KB, cdx)}

Supporting information file. DOI: 10.1107/S1600536814014317/jj2188Isup3.cdx

Click here for additional data file.^{(6.2KB, cml)}

Supporting information file. DOI: 10.1107/S1600536814014317/jj2188Isup4.cml

CCDC reference: 977614

Additional supporting information: crystallographic information; 3D view; checkCIF report

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

Cg1, Cg2 and Cg3 are the centroids of the C2–C7 methylbenzene, C11–C16 benzene and C17–C22 phenyl rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1C⋯Cg2ⁱ	0.96	2.97	3.6689 (17)	131
C5—H5⋯Cg3ⁱⁱ	0.93	2.84	3.5126 (18)	130
C21—H21⋯Cg1ⁱⁱⁱ	0.93	2.99	3.632 (2)	127

Open in a new tab

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

Acknowledgments

The authors are thankful to the Sophisticated Analytical Instrument Facility (SAIF), IITM, Chennai 600 036, Tamilnadu, India, for the single-crystal X-ray data.

supplementary crystallographic information

S1. Comment

Bioactivities of chalcones were reported by Dimmock et al., (1999). The antibacterial, fungistatic and fungicidal properties of these compounds have also been reviewed (Opletalova et al. 2000, 1999). In addition with appropriate substituents, chalcones are a class of non-linear optical materials (Fichou et al. 1988, Goto et al. 1991). Recently, it has been noted that among many organic second harmonic generation, chalcone derivatives have excellent blue light transmittance and good cyrstallizability (Sarojini et al. 2006). The related compounds whose structures have been solved by X-ray are (2E)-1-(4,4''-Difluoro-5'-methoxy-1,1':3',1''-terphenyl-4'-yl)- 3-(4-fluorophenyl)prop-2-en-1-one (Betz et al. 2011a) and (E)-1-(4,4''-Difluoro-5'-methoxy-1,1':3',1''-terphenyl-4' -yl)-3-(4-nitrophenyl)prop-2-en-1-one (Betz et al. 2011b).

In the title molecule (Fig. 1), C₂₂H₁₈O, the o-tolyl ring is connected through a conjugated double bond. The molecule adopts an E configuration and the C7—C8—C9—C10 torsion angle is 178.77 (13)°. Further, the torsion angle [C8—C9—C10—C11 = -164.91 (13)°] shows that the prop-2-en-1-one unit is not planar. The overall conformation of the compound may be described by the values of dihedral angles between the different planes. The terminal rings (C2—C7) and (C17—C22) are twisted by an angle of 54.75 (8)°, while the biphenyl part is not planar, the dihedral angle between the planes of the rings (C11—C16) and (C17—C22) being 40.65 (8)°. The dihedral angle between the benzene rings (C2—C7) and (C11—C16) is 14.10 (7)°.

There are three weak C1—H1C···π, C5—H5···π and C21—H21···π interactions involving the central benzene ring (C11—C16), the terminal phenyl ring (C17—C22) and the terminal benzene ring (C2—C7), respectively, are found in the crystal structure. The C_ar—Csp³, C_ar—C_ar and C═O bond lengths in (I) are within their normal ranges (Allen et al., 1987). No classic hydrogen bonds are observed.

S2. Experimental

Biphenyl acetone (1.06 g, 10 mmol) and 2-methylbenzaldehyde (1.06 g, 10 mmol) in ethanol (25 ml) is mixed in the presence of NaOH (10 ml 30%). The reaction mixture was stirred for 6 h. Then the contents of the flask were poured into ice cold water (250 ml) and left for 12 h. The solid obtained was filtered and recrystallized for three to four times with ethanol. The colourless single crystals of the title compound used for X-ray diffraction studies were grown by slow evaporation of acetone. Yield: 1.48 g (70%).