Crystal structure of (E)-1-([1,1′-biphen­yl]-4-yl)-3-(3-nitro­phen­yl)prop-2-en-1-one

D Shanthi; T Vidhyasagar; K Rajeswari; M Kayalvizhi; G Vasuki; A Thiruvalluvar

doi:10.1107/S2056989015000523

. 2015 Jan 17;71(Pt 2):o119–o120. doi: 10.1107/S2056989015000523

Crystal structure of (E)-1-([1,1′-biphenyl]-4-yl)-3-(3-nitrophenyl)prop-2-en-1-one

D Shanthi ^a, T Vidhyasagar ^a, K Rajeswari ^a, M Kayalvizhi ^b, G Vasuki ^b, A Thiruvalluvar ^c,^*

PMCID: PMC4384577 PMID: 25878861

Abstract

In the title compound, C₂₁H₁₅NO₃, the molecule has an E conformation about the C=C bond, and the C—C=C—C torsion angle is −178.24 (18)°. In the molecule, the planes of the terminal rings are twisted by an angle of 42.19 (10)°, while the biphenyl part is not planar, with a dihedral angle between the rings of 39.2 (1)°. The dihedral angle between the nitrophenyl ring and the inner benzene ring is 5.56 (9)°. The 3-nitro group is approximately coplanar with the benzene ring to which it is attached [O—N—C—C = 0.1 (3)°]. In the crystal, molecules are linked via C—H⋯π interactions, involving the terminal benzene rings, forming corrugated layers parallel to (100).

Keywords: crystal structure, chalcones, C—H⋯π interactions

Related literature

For the biological activities of chalcones, see: Nowakowska (2007 ▸); Liu et al. (2008 ▸); Wu et al. (2010 ▸); Singh et al. (2012 ▸). For non-linear optical (NLO) properties of chalcone derivatives, see: Uchida et al. (1998 ▸); Indira et al. (2002 ▸). For the crystal structures of related compounds, see: Shanthi et al. (2014 ▸); Vidhyasagar et al. (2015a ▸,b ▸). graphic file with name e-71-0o119-scheme1.jpg

Experimental

Crystal data

C₂₁H₁₅NO₃
M _r = 329.34
Monoclinic,
a = 17.6546 (5) Å
b = 6.1464 (2) Å
c = 30.0234 (9) Å
β = 99.899 (4)°
V = 3209.40 (17) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.35 × 0.35 × 0.30 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ▸) T _min = 0.691, T _max = 0.745
26025 measured reflections
3170 independent reflections
2500 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.138
S = 1.08
3170 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.26 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: SIR92 (Altomare et al., 1994 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸) and Mercury (Macrae et al., 2008 ▸); software used to prepare material for publication: SHELXL2014, PLATON (Spek, 2009 ▸) and publCIF (Westrip, 2010 ▸).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015000523/su5060sup1.cif

e-71-0o119-sup1.cif^{(19.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015000523/su5060Isup2.hkl

e-71-0o119-Isup2.hkl^{(174.2KB, hkl)}

Click here for additional data file.^{(2.8KB, cdx)}

Supporting information file. DOI: 10.1107/S2056989015000523/su5060Isup3.cdx

Click here for additional data file.^{(2.7KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015000523/su5060Isup4.cml

Click here for additional data file.^{(1.2MB, tif)}

. DOI: 10.1107/S2056989015000523/su5060fig1.tif

The molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

Click here for additional data file.^{(1.7MB, tif)}

b . DOI: 10.1107/S2056989015000523/su5060fig2.tif

A view along the b axis of the crystal packing of the title compound. The C-H⋯π interactions are shown as dashed lines (see Table 1 for details; for clarity only the H atoms participating in these interactions are shown).

CCDC reference: 991338

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

Table 1. Hydrogen-bond geometry (, ).

Cg1 and Cg3 are the centroids of the nitrobenzene ring C1C6 and the phenyl ring C16C21, respectively.

DHA	DH	HA	D A	DHA
C17H17Cg1ⁱ	0.93	2.93	3.637(2)	133
C20H20Cg3ⁱⁱ	0.93	2.90	3.565(2)	129

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

Acknowledgments

The authors are grateful 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

Chalcones and their analogs have been used for a wide range of biological activities, including antimicrobial, antitumor, anti-inflammatory, antifungal and antioxidant activities (Nowakowska, 2007; Liu et al. 2008; Wu et al. 2010; Singh et al. 2012). Chalcone derivatives also show considerable promise as organic non-linear optical materials (Uchida et al., 1998; Indira et al., (2002). The crystal structures of related compounds have been reported (Shanthi et al., 2014; Vidhyasagar et al., 2015a,b). As part of our on-going research on biphenyl chalcone derivatives, the title compound was synthesized and its crystal structure is reported on herein.

In the title compound, Fig. 1, the molecule exists as an E conformer with the C3—C7—C8—C9 torsion angle being -178.24 (18)°. The terminal rings (C1—C6) and (C16—C21) are twisted by an angle of 42.19 (10)°, while the biphenyl (C10—C15 and C16—C21) part is not planar, the dihedral angle between the planes of these rings being 39.2 (1)°. The dihedral angle between the benzene rings (C1—C6) and (C10—C15) is 5.56 (9)°. The 3-nitro group is approximately coplanar with the benzene ring to which it is attached [O2—N1—C1—C2 = 0.1 (3)°].

In the crystal, molecules are linked via C-H···π interactions, involving the terminal benzene rings (C1—C6) and (C16—C21), forming corrugated layers parallel to (100); see Table 1 and Fig. 2.

S2. Experimental

A mixture of 4-acetylbiphenyl (1.96 g, 10 mmol) and 3-nitro benzaldehyde (1.07 g, 10 mmol) in ethanol (25 ml) in the presence of NaOH (10 ml 30%) were heated in a water bath for 30 min. and then allowed to cool. The solid that separated was filtered and recrystallized from ethanol. The yellow crystals of the title compound used for the X-ray diffraction study were grown by slow evaporation from acetone (yield: 2.5 g; 75%).