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

In the title compound, C22H17NO3, the mol-ecule has an E conformation about the C=C bond, and the C-C=C-C torsion angle is -177.7 (3)°. The planes of the terminal benzene rings are twisted by 41.62 (16)°, while the biphenyl unit is non-planar, the dihedral angle between the planes of the rings being 38.02 (15)°. The dihedral angle between the nitro-phenyl ring and the inner benzene ring is 5.29 (16)°. In the crystal, mol-ecules are linked by two weak C-H⋯π inter-actions, forming rectangular tubes propagating along the b-axis direction.

Related literature

For the synthesis, anti­microbial, anti­oxidant activities and growth and characterization of π-conjugated organic non-linear optical chalcone derivatives, see: Rajendra Prasad et al. (2008 ▸); Lahsasni et al. (2014 ▸); Prabhu et al. (2013 ▸). For the analysis of Bovine serum albumin in the presence of some phenyl-substituted chalcones, see: Garg et al. (2013 ▸). For the crystal structures of related compounds, see: Shanthi et al. (2014 ▸); Vidhyasagar et al. (2015 ▸).

Experimental

Crystal data

C22H17NO3

M = 343.37

Monoclinic,

a = 17.8214 (10) Å

b = 6.1630 (3) Å

c = 32.3569 (19) Å

β = 103.165 (2)°

V = 3460.5 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▸) T min = 0.646, T max = 0.745

17009 measured reflections

2902 independent reflections

2058 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.177

S = 1.08

2902 reflections

236 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.22 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: SIR2002 (Burla et al., 2003 ▸); 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, PLATON publCIF (Westrip, 2010 ▸).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989014027443/su5045sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989014027443/su5045Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989014027443/su5045Isup3.cdx

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989014027443/su5045Isup4.cml

Click here for additional data file.

. DOI: 10.1107/S2056989014027443/su5045fig1.tif

The mol­ecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.

Click here for additional data file.

. DOI: 10.1107/S2056989014027443/su5045fig2.tif

The partial packing of the title compound, showing the two weak C—H⋯π inter­actions (see Table 1 for details).

CCDC reference: 1039539

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

C22H17NO3	F(000) = 1440
Mr = 343.37	Dx = 1.318 Mg m−3
Monoclinic, C2/c	Melting point: 462.3 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 17.8214 (10) Å	Cell parameters from 5055 reflections
b = 6.1630 (3) Å	θ = 2.4–23.5°
c = 32.3569 (19) Å	µ = 0.09 mm−1
β = 103.165 (2)°	T = 293 K
V = 3460.5 (3) Å3	Block, yellow
Z = 8	0.30 × 0.20 × 0.20 mm

Bruker Kappa APEXII CCD diffractometer	2902 independent reflections
Radiation source: fine-focus sealed tube	2058 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.053
ω and φ scan	θmax = 24.7°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −20→20
Tmin = 0.646, Tmax = 0.745	k = −7→7
17009 measured reflections	l = −37→37

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.067	H-atom parameters constrained
wR(F2) = 0.177	w = 1/[σ2(Fo2) + (0.0622P)2 + 6.9426P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
2902 reflections	Δρmax = 0.37 e Å−3
236 parameters	Δρmin = −0.22 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	0.5576 (2)	−0.0419 (5)	−0.18992 (10)	0.1050 (16)
O2	0.57708 (17)	0.2525 (5)	−0.15451 (8)	0.0826 (11)
O3	0.39470 (16)	0.5129 (4)	0.01333 (8)	0.0742 (10)
N1	0.55103 (17)	0.0708 (6)	−0.16008 (9)	0.0619 (11)
C1	0.50961 (16)	−0.0197 (5)	−0.12946 (9)	0.0448 (10)
C2	0.48178 (19)	−0.2286 (6)	−0.13485 (11)	0.0571 (12)
C3	0.4412 (2)	−0.3050 (5)	−0.10630 (12)	0.0619 (14)
C4	0.42788 (19)	−0.1752 (5)	−0.07404 (11)	0.0543 (12)
C5	0.45527 (18)	0.0367 (5)	−0.06918 (9)	0.0442 (10)
C6	0.49828 (17)	0.1111 (5)	−0.09729 (9)	0.0427 (10)
C7	0.43736 (19)	0.1877 (5)	−0.03729 (9)	0.0517 (11)
C8	0.38766 (19)	0.1586 (5)	−0.01312 (10)	0.0524 (11)
C9	0.37335 (18)	0.3262 (5)	0.01629 (10)	0.0495 (11)
C10	0.33265 (17)	0.2675 (5)	0.05025 (9)	0.0411 (10)
C11	0.30439 (18)	0.0609 (5)	0.05492 (10)	0.0481 (11)
C12	0.26955 (18)	0.0165 (5)	0.08822 (10)	0.0479 (11)
C13	0.26254 (17)	0.1744 (5)	0.11789 (9)	0.0398 (9)
C14	0.2909 (2)	0.3785 (5)	0.11259 (10)	0.0527 (11)
C15	0.32487 (19)	0.4245 (5)	0.07947 (10)	0.0525 (11)
C16	0.22680 (17)	0.1252 (5)	0.15388 (9)	0.0411 (10)
C17	0.23877 (18)	−0.0738 (5)	0.17499 (10)	0.0484 (11)
C18	0.20358 (19)	−0.1232 (5)	0.20751 (10)	0.0527 (11)
C19	0.15524 (19)	0.0243 (6)	0.22083 (10)	0.0529 (11)
C20	0.14488 (18)	0.2233 (6)	0.20100 (10)	0.0542 (11)
C21	0.17998 (18)	0.2742 (5)	0.16818 (10)	0.0491 (11)
C22	0.1162 (2)	−0.0328 (8)	0.25609 (12)	0.0813 (18)
H2	0.49001	−0.31504	−0.15695	0.0685*
H3	0.42262	−0.44648	−0.10885	0.0742*
H4	0.40014	−0.23004	−0.05526	0.0652*
H6	0.51930	0.24991	−0.09416	0.0512*
H7	0.46418	0.31838	−0.03384	0.0616*
H8	0.36098	0.02805	−0.01481	0.0628*
H11	0.30885	−0.04782	0.03569	0.0576*
H12	0.25041	−0.12199	0.09077	0.0572*
H14	0.28687	0.48747	0.13186	0.0631*
H15	0.34298	0.56398	0.07669	0.0626*
H17	0.27127	−0.17533	0.16688	0.0578*
H18	0.21237	−0.25769	0.22078	0.0632*
H20	0.11360	0.32586	0.20984	0.0650*
H21	0.17207	0.41032	0.15553	0.0588*
H22A	0.15172	−0.10892	0.27806	0.1225*
H22B	0.07234	−0.12346	0.24514	0.1225*
H22C	0.09953	0.09766	0.26755	0.1225*

	U11	U22	U33	U12	U13	U23
O1	0.131 (3)	0.115 (3)	0.090 (2)	−0.020 (2)	0.069 (2)	−0.045 (2)
O2	0.102 (2)	0.080 (2)	0.0823 (19)	−0.0289 (17)	0.0551 (17)	−0.0140 (16)
O3	0.104 (2)	0.0562 (16)	0.0751 (17)	−0.0230 (15)	0.0470 (16)	−0.0017 (13)
N1	0.0566 (18)	0.072 (2)	0.063 (2)	−0.0032 (16)	0.0260 (15)	−0.0152 (17)
C1	0.0358 (16)	0.051 (2)	0.0489 (18)	0.0039 (15)	0.0121 (14)	−0.0019 (15)
C2	0.052 (2)	0.051 (2)	0.067 (2)	0.0034 (17)	0.0106 (17)	−0.0158 (18)
C3	0.062 (2)	0.0386 (19)	0.083 (3)	−0.0083 (17)	0.012 (2)	−0.0014 (18)
C4	0.056 (2)	0.049 (2)	0.058 (2)	−0.0107 (16)	0.0130 (16)	0.0048 (16)
C5	0.0493 (18)	0.0413 (18)	0.0405 (16)	−0.0064 (15)	0.0069 (14)	0.0018 (14)
C6	0.0444 (17)	0.0391 (17)	0.0449 (17)	−0.0019 (14)	0.0109 (14)	−0.0005 (14)
C7	0.064 (2)	0.050 (2)	0.0460 (18)	−0.0110 (16)	0.0227 (16)	−0.0018 (15)
C8	0.060 (2)	0.053 (2)	0.0498 (19)	−0.0167 (17)	0.0244 (17)	−0.0032 (16)
C9	0.053 (2)	0.052 (2)	0.0444 (18)	−0.0119 (16)	0.0133 (15)	−0.0002 (15)
C10	0.0451 (17)	0.0422 (18)	0.0381 (16)	−0.0045 (14)	0.0139 (13)	0.0057 (14)
C11	0.058 (2)	0.0442 (18)	0.0455 (18)	−0.0050 (16)	0.0189 (16)	−0.0059 (14)
C12	0.057 (2)	0.0345 (17)	0.056 (2)	−0.0096 (15)	0.0207 (16)	0.0027 (14)
C13	0.0437 (17)	0.0346 (16)	0.0430 (16)	0.0010 (13)	0.0136 (14)	0.0000 (13)
C14	0.074 (2)	0.0369 (18)	0.0525 (19)	−0.0066 (17)	0.0257 (18)	−0.0051 (15)
C15	0.069 (2)	0.0367 (18)	0.055 (2)	−0.0110 (16)	0.0211 (17)	−0.0010 (15)
C16	0.0449 (18)	0.0383 (17)	0.0405 (16)	−0.0025 (14)	0.0109 (14)	−0.0005 (13)
C17	0.055 (2)	0.0412 (18)	0.0533 (19)	0.0002 (15)	0.0214 (16)	0.0005 (15)
C18	0.063 (2)	0.050 (2)	0.0464 (19)	−0.0043 (17)	0.0155 (17)	0.0082 (15)
C19	0.051 (2)	0.064 (2)	0.0443 (18)	−0.0056 (17)	0.0122 (15)	−0.0019 (17)
C20	0.052 (2)	0.065 (2)	0.0488 (19)	0.0109 (17)	0.0180 (16)	−0.0065 (17)
C21	0.0530 (19)	0.0433 (19)	0.0508 (18)	0.0059 (16)	0.0117 (16)	0.0006 (15)
C22	0.084 (3)	0.110 (4)	0.059 (2)	−0.005 (3)	0.035 (2)	0.002 (2)

O1—N1	1.217 (4)	C17—C18	1.376 (5)
O2—N1	1.210 (5)	C18—C19	1.387 (5)
O3—C9	1.223 (4)	C19—C20	1.377 (5)
N1—C1	1.473 (4)	C19—C22	1.507 (5)
C1—C2	1.376 (5)	C20—C21	1.386 (5)
C1—C6	1.367 (4)	C2—H2	0.9300
C2—C3	1.379 (5)	C3—H3	0.9300
C3—C4	1.378 (5)	C4—H4	0.9300
C4—C5	1.391 (4)	C6—H6	0.9300
C5—C6	1.394 (4)	C7—H7	0.9300
C5—C7	1.477 (4)	C8—H8	0.9300
C7—C8	1.321 (5)	C11—H11	0.9300
C8—C9	1.466 (4)	C12—H12	0.9300
C9—C10	1.493 (4)	C14—H14	0.9300
C10—C11	1.390 (4)	C15—H15	0.9300
C10—C15	1.382 (4)	C17—H17	0.9300
C11—C12	1.388 (5)	C18—H18	0.9300
C12—C13	1.392 (4)	C20—H20	0.9300
C13—C14	1.381 (4)	C21—H21	0.9300
C13—C16	1.480 (4)	C22—H22A	0.9600
C14—C15	1.375 (5)	C22—H22B	0.9600
C16—C17	1.396 (4)	C22—H22C	0.9600
C16—C21	1.389 (4)
O1—N1—O2	122.9 (3)	C19—C20—C21	121.5 (3)
O1—N1—C1	118.1 (3)	C16—C21—C20	121.1 (3)
O2—N1—C1	119.0 (3)	C1—C2—H2	121.00
N1—C1—C2	119.4 (3)	C3—C2—H2	121.00
N1—C1—C6	118.2 (3)	C2—C3—H3	119.00
C2—C1—C6	122.4 (3)	C4—C3—H3	119.00
C1—C2—C3	117.6 (3)	C3—C4—H4	120.00
C2—C3—C4	121.1 (3)	C5—C4—H4	120.00
C3—C4—C5	121.0 (3)	C1—C6—H6	120.00
C4—C5—C6	117.8 (3)	C5—C6—H6	120.00
C4—C5—C7	123.0 (3)	C5—C7—H7	116.00
C6—C5—C7	119.1 (3)	C8—C7—H7	116.00
C1—C6—C5	120.1 (3)	C7—C8—H8	119.00
C5—C7—C8	127.5 (3)	C9—C8—H8	119.00
C7—C8—C9	121.9 (3)	C10—C11—H11	120.00
O3—C9—C8	120.6 (3)	C12—C11—H11	120.00
O3—C9—C10	119.9 (3)	C11—C12—H12	119.00
C8—C9—C10	119.5 (3)	C13—C12—H12	119.00
C9—C10—C11	123.4 (3)	C13—C14—H14	119.00
C9—C10—C15	118.4 (3)	C15—C14—H14	119.00
C11—C10—C15	118.2 (3)	C10—C15—H15	119.00
C10—C11—C12	120.2 (3)	C14—C15—H15	119.00
C11—C12—C13	121.6 (3)	C16—C17—H17	119.00
C12—C13—C14	117.3 (3)	C18—C17—H17	119.00
C12—C13—C16	121.4 (3)	C17—C18—H18	119.00
C14—C13—C16	121.3 (3)	C19—C18—H18	119.00
C13—C14—C15	121.6 (3)	C19—C20—H20	119.00
C10—C15—C14	121.3 (3)	C21—C20—H20	119.00
C13—C16—C17	121.3 (3)	C16—C21—H21	119.00
C13—C16—C21	121.7 (3)	C20—C21—H21	119.00
C17—C16—C21	117.0 (3)	C19—C22—H22A	110.00
C16—C17—C18	121.5 (3)	C19—C22—H22B	110.00
C17—C18—C19	121.1 (3)	C19—C22—H22C	109.00
C18—C19—C20	117.8 (3)	H22A—C22—H22B	109.00
C18—C19—C22	120.6 (3)	H22A—C22—H22C	109.00
C20—C19—C22	121.7 (3)	H22B—C22—H22C	109.00
O1—N1—C1—C2	1.7 (5)	C15—C10—C11—C12	0.0 (5)
O1—N1—C1—C6	−176.3 (3)	C9—C10—C15—C14	−177.2 (3)
O2—N1—C1—C2	−178.1 (3)	C11—C10—C15—C14	0.7 (5)
O2—N1—C1—C6	3.9 (5)	C10—C11—C12—C13	−0.7 (5)
N1—C1—C2—C3	−178.0 (3)	C11—C12—C13—C14	0.8 (5)
C6—C1—C2—C3	0.0 (5)	C11—C12—C13—C16	−178.7 (3)
N1—C1—C6—C5	176.0 (3)	C12—C13—C14—C15	−0.1 (5)
C2—C1—C6—C5	−1.9 (5)	C16—C13—C14—C15	179.3 (3)
C1—C2—C3—C4	1.2 (5)	C12—C13—C16—C17	37.9 (4)
C2—C3—C4—C5	−0.3 (5)	C12—C13—C16—C21	−142.1 (3)
C3—C4—C5—C6	−1.7 (5)	C14—C13—C16—C17	−141.5 (3)
C3—C4—C5—C7	175.0 (3)	C14—C13—C16—C21	38.5 (5)
C4—C5—C6—C1	2.7 (5)	C13—C14—C15—C10	−0.6 (5)
C7—C5—C6—C1	−174.1 (3)	C13—C16—C17—C18	−177.7 (3)
C4—C5—C7—C8	−8.8 (5)	C21—C16—C17—C18	2.3 (5)
C6—C5—C7—C8	167.9 (3)	C13—C16—C21—C20	177.9 (3)
C5—C7—C8—C9	−177.7 (3)	C17—C16—C21—C20	−2.1 (5)
C7—C8—C9—O3	15.0 (5)	C16—C17—C18—C19	−0.6 (5)
C7—C8—C9—C10	−164.7 (3)	C17—C18—C19—C20	−1.3 (5)
O3—C9—C10—C11	177.9 (3)	C17—C18—C19—C22	179.2 (3)
O3—C9—C10—C15	−4.4 (5)	C18—C19—C20—C21	1.4 (5)
C8—C9—C10—C11	−2.4 (5)	C22—C19—C20—C21	−179.1 (3)
C8—C9—C10—C15	175.3 (3)	C19—C20—C21—C16	0.3 (5)
C9—C10—C11—C12	177.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Cg3i	0.93	2.99	3.531 (4)	119
C21—H21···Cg1ii	0.93	2.94	3.607 (3)	129

Table 1

Hydrogen-bond geometry (, )

Cg1 and Cg3 are the centroids of rings C1C6 and C16C21, respectively.

DHA	DH	HA	D A	DHA
C3H3Cg3i	0.93	2.99	3.531(4)	119
C21H21Cg1ii	0.93	2.94	3.607(3)	129

Symmetry codes: (i) ; (ii) .