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

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

doi:10.1107/S2056989015000523

organic compounds

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ISSN: 2056-9890

Volume 71| Part 2| February 2015| Pages o119-o120

doi:10.1107/S2056989015000523

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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 and A. Thiruvalluvar ^c ^*

^aDepartment of Chemistry, Annamalai University, Annamalai Nagar 608 002, Tamilnadu, India, ^bDepartment of Physics, Kunthavai Naachiar Government Arts College (W) (Autonomous), Thanjavur 613 007, Tamilnadu, India, and ^cPostgraduate Research Department of Physics, Rajah Serfoji Government College (Autonomous), Thanjavur 613 005, Tamilnadu, India
^*Correspondence e-mail: thiruvalluvar.a@gmail.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 8 January 2015; accepted 11 January 2015; online 17 January 2015)

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.

CCDC reference: 991338

1. 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 ).

2. Experimental

2.1. Crystal data

C₂₁H₁₅NO₃
M_r = 329.34
Monoclinic, C 2/c
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

2.2. 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

2.3. Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 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

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg3 are the centroids of the nitrobenzene ring C1–C6 and the phenyl ring C16–C21, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17⋯Cg1ⁱ	0.93	2.93	3.637 (2)	133
C20—H20⋯Cg3ⁱⁱ	0.93	2.90	3.565 (2)	129
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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 ).

Supporting information

CCDC reference: 991338

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2056989015000523/su5060sup1.cif

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

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

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

checkCIF report

Comment top

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.

Related literature top

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).

Experimental top

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%).

Computing details top

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 (Sheldrick, 2015), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. 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).

(E)-1-([1,1'-Biphenyl]-4-yl)-3-(3-nitrophenyl)prop-2-en-1-one top

Crystal data top

C₂₁H₁₅NO₃	F(000) = 1376
M_r = 329.34	D_x = 1.363 Mg m⁻³
Monoclinic, C2/c	Melting point: 462.9 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 17.6546 (5) Å	Cell parameters from 9326 reflections
b = 6.1464 (2) Å	θ = 2.5–15.9°
c = 30.0234 (9) Å	µ = 0.09 mm⁻¹
β = 99.899 (4)°	T = 296 K
V = 3209.40 (17) Å³	Block, yellow
Z = 8	0.35 × 0.35 × 0.30 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	3170 independent reflections
Radiation source: fine-focus sealed tube	2500 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ω and ϕ scan	θ_max = 26.1°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −21→21
T_min = 0.691, T_max = 0.745	k = −7→7
26025 measured reflections	l = −37→36

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.138	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0541P)² + 3.3754P] where P = (F_o² + 2F_c²)/3
3170 reflections	(Δ/σ)_max < 0.001
226 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₂₁H₁₅NO₃	V = 3209.40 (17) Å³
M_r = 329.34	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 17.6546 (5) Å	µ = 0.09 mm⁻¹
b = 6.1464 (2) Å	T = 296 K
c = 30.0234 (9) Å	0.35 × 0.35 × 0.30 mm
β = 99.899 (4)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3170 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2500 reflections with I > 2σ(I)
T_min = 0.691, T_max = 0.745	R_int = 0.026
26025 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.138	H-atom parameters constrained
S = 1.08	Δρ_max = 0.26 e Å⁻³
3170 reflections	Δρ_min = −0.17 e Å⁻³
226 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.57652 (12)	0.4252 (3)	−0.19910 (6)	0.0883 (8)
O2	0.58837 (11)	0.7332 (3)	−0.16537 (6)	0.0773 (7)
O3	0.39281 (11)	1.0140 (3)	0.01671 (6)	0.0693 (6)
N1	0.56468 (10)	0.5469 (3)	−0.16914 (6)	0.0562 (7)
C1	0.51892 (10)	0.4648 (3)	−0.13607 (6)	0.0420 (6)
C2	0.50490 (10)	0.6028 (3)	−0.10237 (6)	0.0407 (6)
C3	0.45859 (11)	0.5329 (3)	−0.07197 (6)	0.0404 (6)
C4	0.43071 (12)	0.3208 (3)	−0.07611 (7)	0.0486 (7)
C5	0.44639 (12)	0.1864 (3)	−0.10995 (8)	0.0544 (7)
C6	0.49053 (12)	0.2569 (4)	−0.14085 (7)	0.0506 (7)
C7	0.43910 (11)	0.6866 (3)	−0.03818 (6)	0.0458 (6)
C8	0.38646 (11)	0.6597 (3)	−0.01229 (7)	0.0475 (7)
C9	0.37029 (11)	0.8276 (3)	0.01956 (6)	0.0454 (6)
C10	0.32643 (10)	0.7680 (3)	0.05601 (6)	0.0398 (6)
C11	0.31668 (12)	0.9253 (3)	0.08779 (7)	0.0487 (7)
C12	0.27956 (12)	0.8788 (3)	0.12315 (7)	0.0485 (7)
C13	0.25004 (11)	0.6723 (3)	0.12863 (6)	0.0386 (5)
C14	0.25952 (11)	0.5155 (3)	0.09672 (6)	0.0422 (6)
C15	0.29722 (11)	0.5609 (3)	0.06115 (6)	0.0433 (6)
C16	0.21041 (11)	0.6233 (3)	0.16715 (6)	0.0397 (6)
C17	0.16140 (11)	0.7741 (3)	0.18176 (7)	0.0470 (6)
C18	0.12348 (13)	0.7254 (4)	0.21715 (7)	0.0570 (8)
C19	0.13376 (13)	0.5265 (4)	0.23841 (7)	0.0586 (8)
C20	0.18328 (13)	0.3770 (4)	0.22494 (7)	0.0545 (7)
C21	0.22157 (12)	0.4246 (3)	0.18959 (6)	0.0461 (6)
H2	0.52615	0.74161	−0.09987	0.0488*
H4	0.40097	0.26912	−0.05564	0.0582*
H5	0.42694	0.04543	−0.11206	0.0653*
H6	0.50062	0.16684	−0.16403	0.0607*
H7	0.46667	0.81623	−0.03468	0.0549*
H8	0.35878	0.53030	−0.01430	0.0570*
H11	0.33570	1.06482	0.08500	0.0584*
H12	0.27398	0.98736	0.14392	0.0582*
H14	0.23999	0.37647	0.09938	0.0506*
H15	0.30313	0.45231	0.04045	0.0520*
H17	0.15406	0.90890	0.16762	0.0564*
H18	0.09084	0.82768	0.22665	0.0683*
H19	0.10733	0.49326	0.26179	0.0703*
H20	0.19103	0.24360	0.23963	0.0654*
H21	0.25507	0.32293	0.18074	0.0554*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.1143 (15)	0.0909 (14)	0.0732 (12)	−0.0074 (12)	0.0544 (11)	−0.0205 (11)
O2	0.0927 (13)	0.0690 (12)	0.0825 (12)	−0.0205 (10)	0.0494 (10)	−0.0031 (10)
O3	0.0946 (12)	0.0492 (9)	0.0733 (11)	−0.0190 (9)	0.0408 (10)	−0.0026 (8)
N1	0.0556 (11)	0.0650 (13)	0.0523 (10)	0.0023 (10)	0.0215 (9)	−0.0020 (9)
C1	0.0377 (10)	0.0457 (11)	0.0434 (10)	0.0031 (8)	0.0092 (8)	0.0021 (8)
C2	0.0402 (10)	0.0382 (10)	0.0442 (10)	−0.0031 (8)	0.0088 (8)	0.0019 (8)
C3	0.0422 (10)	0.0416 (10)	0.0370 (9)	−0.0048 (8)	0.0056 (8)	0.0031 (8)
C4	0.0500 (11)	0.0459 (12)	0.0503 (11)	−0.0088 (9)	0.0102 (9)	0.0054 (9)
C5	0.0563 (13)	0.0384 (11)	0.0686 (14)	−0.0081 (10)	0.0107 (10)	−0.0008 (10)
C6	0.0488 (11)	0.0497 (12)	0.0527 (12)	0.0032 (10)	0.0067 (9)	−0.0095 (10)
C7	0.0531 (12)	0.0428 (11)	0.0431 (10)	−0.0056 (9)	0.0132 (9)	−0.0008 (9)
C8	0.0507 (11)	0.0485 (12)	0.0462 (11)	−0.0119 (9)	0.0168 (9)	−0.0038 (9)
C9	0.0480 (11)	0.0453 (11)	0.0434 (10)	−0.0076 (9)	0.0092 (8)	−0.0002 (9)
C10	0.0417 (10)	0.0395 (10)	0.0383 (9)	−0.0011 (8)	0.0074 (8)	0.0017 (8)
C11	0.0619 (13)	0.0327 (10)	0.0537 (12)	−0.0081 (9)	0.0166 (10)	−0.0037 (9)
C12	0.0684 (13)	0.0342 (10)	0.0460 (11)	−0.0029 (9)	0.0183 (10)	−0.0070 (9)
C13	0.0440 (10)	0.0342 (9)	0.0369 (9)	0.0023 (8)	0.0051 (8)	−0.0004 (8)
C14	0.0531 (11)	0.0316 (9)	0.0432 (10)	−0.0051 (8)	0.0124 (9)	−0.0014 (8)
C15	0.0519 (11)	0.0384 (10)	0.0414 (10)	−0.0036 (9)	0.0129 (8)	−0.0072 (8)
C16	0.0457 (10)	0.0374 (10)	0.0353 (9)	−0.0015 (8)	0.0049 (8)	−0.0034 (8)
C17	0.0542 (12)	0.0417 (11)	0.0446 (10)	0.0055 (9)	0.0069 (9)	−0.0014 (9)
C18	0.0578 (13)	0.0665 (15)	0.0493 (12)	0.0100 (11)	0.0170 (10)	−0.0055 (11)
C19	0.0648 (14)	0.0724 (16)	0.0415 (11)	−0.0057 (12)	0.0175 (10)	−0.0007 (11)
C20	0.0713 (14)	0.0500 (12)	0.0424 (11)	−0.0045 (11)	0.0107 (10)	0.0051 (9)
C21	0.0580 (12)	0.0384 (10)	0.0423 (10)	0.0015 (9)	0.0095 (9)	−0.0021 (8)

Geometric parameters (Å, º) top

O1—N1	1.215 (3)	C16—C17	1.390 (3)
O2—N1	1.218 (3)	C16—C21	1.392 (3)
O3—C9	1.221 (3)	C17—C18	1.383 (3)
N1—C1	1.473 (3)	C18—C19	1.377 (3)
C1—C2	1.375 (3)	C19—C20	1.376 (3)
C1—C6	1.371 (3)	C20—C21	1.384 (3)
C2—C3	1.394 (3)	C2—H2	0.9300
C3—C4	1.392 (3)	C4—H4	0.9300
C3—C7	1.470 (3)	C5—H5	0.9300
C4—C5	1.374 (3)	C6—H6	0.9300
C5—C6	1.380 (3)	C7—H7	0.9300
C7—C8	1.320 (3)	C8—H8	0.9300
C8—C9	1.468 (3)	C11—H11	0.9300
C9—C10	1.491 (3)	C12—H12	0.9300
C10—C11	1.390 (3)	C14—H14	0.9300
C10—C15	1.392 (3)	C15—H15	0.9300
C11—C12	1.370 (3)	C17—H17	0.9300
C12—C13	1.393 (3)	C18—H18	0.9300
C13—C14	1.389 (3)	C19—H19	0.9300
C13—C16	1.482 (3)	C20—H20	0.9300
C14—C15	1.381 (3)	C21—H21	0.9300

O1—N1—O2	123.20 (19)	C18—C19—C20	119.8 (2)
O1—N1—C1	118.18 (18)	C19—C20—C21	120.2 (2)
O2—N1—C1	118.62 (17)	C16—C21—C20	120.62 (19)
N1—C1—C2	118.28 (16)	C1—C2—H2	120.00
N1—C1—C6	118.80 (17)	C3—C2—H2	120.00
C2—C1—C6	122.90 (18)	C3—C4—H4	119.00
C1—C2—C3	119.46 (17)	C5—C4—H4	119.00
C2—C3—C4	117.94 (17)	C4—C5—H5	119.00
C2—C3—C7	119.16 (17)	C6—C5—H5	119.00
C4—C3—C7	122.87 (17)	C1—C6—H6	121.00
C3—C4—C5	121.08 (19)	C5—C6—H6	121.00
C4—C5—C6	121.14 (19)	C3—C7—H7	117.00
C1—C6—C5	117.44 (19)	C8—C7—H7	117.00
C3—C7—C8	126.72 (18)	C7—C8—H8	119.00
C7—C8—C9	122.06 (17)	C9—C8—H8	119.00
O3—C9—C8	120.80 (18)	C10—C11—H11	119.00
O3—C9—C10	119.91 (18)	C12—C11—H11	119.00
C8—C9—C10	119.28 (16)	C11—C12—H12	119.00
C9—C10—C11	118.31 (17)	C13—C12—H12	119.00
C9—C10—C15	123.72 (16)	C13—C14—H14	119.00
C11—C10—C15	117.91 (17)	C15—C14—H14	119.00
C10—C11—C12	121.27 (17)	C10—C15—H15	120.00
C11—C12—C13	121.35 (18)	C14—C15—H15	120.00
C12—C13—C14	117.32 (17)	C16—C17—H17	120.00
C12—C13—C16	120.93 (17)	C18—C17—H17	120.00
C14—C13—C16	121.75 (17)	C17—C18—H18	120.00
C13—C14—C15	121.64 (17)	C19—C18—H18	120.00
C10—C15—C14	120.51 (17)	C18—C19—H19	120.00
C13—C16—C17	120.93 (17)	C20—C19—H19	120.00
C13—C16—C21	120.62 (17)	C19—C20—H20	120.00
C17—C16—C21	118.45 (17)	C21—C20—H20	120.00
C16—C17—C18	120.55 (19)	C16—C21—H21	120.00
C17—C18—C19	120.4 (2)	C20—C21—H21	120.00

O1—N1—C1—C2	−179.46 (19)	C9—C10—C11—C12	−177.45 (19)
O2—N1—C1—C2	0.1 (3)	C15—C10—C11—C12	0.0 (3)
O1—N1—C1—C6	−1.1 (3)	C9—C10—C15—C14	177.65 (18)
O2—N1—C1—C6	178.40 (19)	C11—C10—C15—C14	0.3 (3)
N1—C1—C2—C3	176.84 (17)	C10—C11—C12—C13	−0.1 (3)
C6—C1—C2—C3	−1.4 (3)	C11—C12—C13—C14	−0.2 (3)
N1—C1—C6—C5	−178.54 (18)	C11—C12—C13—C16	179.62 (19)
C2—C1—C6—C5	−0.3 (3)	C12—C13—C14—C15	0.6 (3)
C1—C2—C3—C4	2.5 (3)	C16—C13—C14—C15	−179.26 (18)
C1—C2—C3—C7	−175.45 (17)	C12—C13—C16—C17	39.4 (3)
C2—C3—C4—C5	−1.9 (3)	C12—C13—C16—C21	−140.6 (2)
C7—C3—C4—C5	175.90 (19)	C14—C13—C16—C17	−140.8 (2)
C2—C3—C7—C8	167.81 (19)	C14—C13—C16—C21	39.3 (3)
C4—C3—C7—C8	−10.0 (3)	C13—C14—C15—C10	−0.6 (3)
C3—C4—C5—C6	0.3 (3)	C13—C16—C17—C18	178.72 (19)
C4—C5—C6—C1	0.9 (3)	C21—C16—C17—C18	−1.4 (3)
C3—C7—C8—C9	−178.24 (18)	C13—C16—C21—C20	−178.60 (19)
C7—C8—C9—O3	15.5 (3)	C17—C16—C21—C20	1.5 (3)
C7—C8—C9—C10	−163.88 (18)	C16—C17—C18—C19	0.0 (3)
O3—C9—C10—C11	−4.1 (3)	C17—C18—C19—C20	1.3 (3)
O3—C9—C10—C15	178.56 (19)	C18—C19—C20—C21	−1.2 (3)
C8—C9—C10—C11	175.31 (18)	C19—C20—C21—C16	−0.2 (3)
C8—C9—C10—C15	−2.0 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg3 are the centroids of the nitrobenzene ring C1–C6 and the phenyl ring C16–C21, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···Cg1ⁱ	0.93	2.93	3.637 (2)	133
C20—H20···Cg3ⁱⁱ	0.93	2.90	3.565 (2)	129

Symmetry codes: (i) −x+1/2, −y+3/2, −z; (ii) −x+1/2, y−1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg3 are the centroids of the nitrobenzene ring C1–C6 and the phenyl ring C16–C21, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···Cg1ⁱ	0.93	2.93	3.637 (2)	133
C20—H20···Cg3ⁱⁱ	0.93	2.90	3.565 (2)	129

Symmetry codes: (i) −x+1/2, −y+3/2, −z; (ii) −x+1/2, y−1/2, −z+1/2.

Acknowledgements

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

References

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Volume 71| Part 2| February 2015| Pages o119-o120

doi:10.1107/S2056989015000523

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

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