Crystal structure of (E)-1-([1,1'-biphen-yl]-4-yl)-3-(3-nitro-phen-yl)prop-2-en-1-one.

In the title compound, C21H15NO3, the mol-ecule has an E conformation about the C=C bond, and the C-C=C-C torsion angle is -178.24 (18)°. In the mol-ecule, 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 nitro-phenyl 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, mol-ecules are linked via C-H⋯π inter-actions, involving the terminal benzene rings, forming corrugated layers parallel to (100).

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 ▸).

Experimental

Crystal data

C21H15NO3

M = 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

Δρmax = 0.26 e Å−3

Δρmin = −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 ▸).

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

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

Click here for additional data file.

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

Click here for additional data file.

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

Click here for additional data file.

. 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.

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

C21H15NO3	F(000) = 1376
Mr = 329.34	Dx = 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

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

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(Fo2) + (0.0541P)2 + 3.3754P] where P = (Fo2 + 2Fc2)/3
3170 reflections	(Δ/σ)max < 0.001
226 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

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

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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

Symmetry codes: (i) ; (ii) .