(2E)-1-(4,4''-Difluoro-5'-meth-oxy-1,1':3',1''-terphenyl-4'-yl)-3-(4-fluoro-phen-yl)prop-2-en-1-one.

In the title compound, C(28)H(19)F(3)O(2), the C=C double bond has an E configuration. In the crystal, C-H⋯F contacts link the mol-ecules into chains along [111]. The shortest centroid-centroid distance between two π systems is 3.8087 (8) Å and is apparent between the para-fluoro-phenyl group attached to the Michael system and its symmetry-generated equivalent.

Related literature

For the pharmacological importance of terphenyls, see: Liu (2006 ▶) and of chalcones, see: Dhar (1981 ▶); Dimmock et al. (1999 ▶); Satyanarayana et al. (2004 ▶). For work on the synthesis and strcutures of different chalcone derivatives, see: Samshuddin et al. (2011a ▶,b ▶); Fun et al. (2010a ▶,b ▶); Jasinski et al. (2010a ▶,b ▶); Baktir et al. (2011a ▶,b ▶). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C28H19F3O2

M = 444.43

Monoclinic,

a = 22.5742 (5) Å

b = 6.8101 (1) Å

c = 13.8475 (3) Å

β = 98.405 (1)°

V = 2105.95 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 200 K

0.56 × 0.26 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer

35196 measured reflections

5218 independent reflections

4087 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.102

S = 1.04

5218 reflections

299 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811042279/zl2413sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811042279/zl2413Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811042279/zl2413Isup3.cdx

Supplementary material file. DOI: 10.1107/S1600536811042279/zl2413Isup4.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C28H19F3O2	F(000) = 920
Mr = 444.43	Dx = 1.402 Mg m−3
Monoclinic, P21/c	Melting point: 549 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 22.5742 (5) Å	Cell parameters from 9830 reflections
b = 6.8101 (1) Å	θ = 3.0–28.3°
c = 13.8475 (3) Å	µ = 0.11 mm−1
β = 98.405 (1)°	T = 200 K
V = 2105.95 (7) Å3	Block, yellow
Z = 4	0.56 × 0.26 × 0.18 mm

Bruker APEXII CCD diffractometer	4087 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.032
graphite	θmax = 28.3°, θmin = 1.8°
φ and ω scans	h = −30→30
35196 measured reflections	k = −9→8
5218 independent reflections	l = −18→18

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0462P)2 + 0.5814P] where P = (Fo2 + 2Fc2)/3
5218 reflections	(Δ/σ)max < 0.001
299 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

	x	y	z	Uiso*/Ueq
F1	−0.04953 (4)	0.88945 (14)	0.40789 (7)	0.0567 (3)
F2	0.37032 (4)	0.00783 (12)	0.22814 (6)	0.0486 (2)
F3	0.53866 (4)	1.35725 (17)	−0.11810 (8)	0.0755 (3)
O1	0.25624 (4)	0.57595 (14)	−0.06967 (7)	0.0445 (2)
O2	0.18161 (4)	1.02710 (14)	−0.05061 (7)	0.0422 (2)
C1	0.25957 (5)	0.72789 (19)	−0.02279 (8)	0.0317 (3)
C2	0.30451 (6)	0.88085 (19)	−0.03214 (9)	0.0343 (3)
H2	0.3015	1.0037	−0.0007	0.041*
C3	0.34907 (5)	0.85151 (19)	−0.08335 (9)	0.0342 (3)
H3	0.3493	0.7298	−0.1168	0.041*
C4	0.15353 (7)	1.2144 (2)	−0.06059 (10)	0.0455 (3)
H4A	0.1662	1.2924	−0.0017	0.068*
H4B	0.1100	1.1977	−0.0695	0.068*
H4C	0.1651	1.2821	−0.1175	0.068*
C11	0.21736 (5)	0.76519 (17)	0.05006 (8)	0.0291 (2)
C12	0.17663 (5)	0.92003 (18)	0.03161 (9)	0.0313 (3)
C13	0.13322 (5)	0.95422 (18)	0.09070 (9)	0.0310 (3)
H13	0.1050	1.0572	0.0756	0.037*
C14	0.13129 (5)	0.83612 (17)	0.17253 (8)	0.0285 (2)
C15	0.17348 (5)	0.68782 (17)	0.19389 (8)	0.0287 (2)
H15	0.1733	0.6120	0.2514	0.034*
C16	0.21618 (5)	0.64726 (17)	0.13284 (8)	0.0279 (2)
C21	0.08371 (5)	0.86298 (16)	0.23502 (9)	0.0289 (2)
C22	0.02421 (5)	0.89054 (18)	0.19403 (9)	0.0331 (3)
H22	0.0143	0.9020	0.1252	0.040*
C23	−0.02064 (6)	0.90140 (18)	0.25208 (10)	0.0375 (3)
H23	−0.0612	0.9206	0.2240	0.045*
C24	−0.00510 (6)	0.88379 (18)	0.35085 (10)	0.0384 (3)
C25	0.05286 (6)	0.8598 (2)	0.39518 (10)	0.0398 (3)
H25	0.0622	0.8508	0.4642	0.048*
C26	0.09725 (6)	0.84925 (18)	0.33614 (9)	0.0345 (3)
H26	0.1377	0.8323	0.3652	0.041*
C31	0.25833 (5)	0.48112 (17)	0.15868 (8)	0.0274 (2)
C32	0.23728 (5)	0.30657 (18)	0.19374 (9)	0.0312 (3)
H32	0.1962	0.2967	0.2010	0.037*
C33	0.27442 (6)	0.14721 (18)	0.21833 (9)	0.0343 (3)
H33	0.2596	0.0294	0.2426	0.041*
C34	0.33354 (6)	0.16525 (18)	0.20640 (9)	0.0333 (3)
C35	0.35695 (5)	0.3347 (2)	0.17383 (9)	0.0352 (3)
H35	0.3982	0.3430	0.1673	0.042*
C36	0.31926 (5)	0.49307 (18)	0.15071 (9)	0.0322 (3)
H36	0.3350	0.6119	0.1290	0.039*
C41	0.39775 (5)	0.9881 (2)	−0.09336 (9)	0.0340 (3)
C42	0.44727 (6)	0.9221 (2)	−0.13332 (10)	0.0425 (3)
H42	0.4484	0.7899	−0.1550	0.051*
C43	0.49492 (6)	1.0455 (3)	−0.14204 (11)	0.0504 (4)
H43	0.5288	0.9998	−0.1690	0.060*
C44	0.49179 (6)	1.2347 (3)	−0.11076 (11)	0.0498 (4)
C45	0.44382 (7)	1.3083 (2)	−0.07209 (10)	0.0473 (3)
H45	0.4431	1.4414	−0.0516	0.057*
C46	0.39656 (6)	1.1840 (2)	−0.06367 (9)	0.0394 (3)
H46	0.3628	1.2322	−0.0374	0.047*

	U11	U22	U33	U12	U13	U23
F1	0.0539 (5)	0.0573 (6)	0.0682 (6)	−0.0014 (4)	0.0407 (4)	−0.0098 (4)
F2	0.0448 (5)	0.0415 (5)	0.0603 (5)	0.0126 (4)	0.0102 (4)	0.0063 (4)
F3	0.0552 (6)	0.0899 (8)	0.0845 (7)	−0.0380 (5)	0.0209 (5)	0.0072 (6)
O1	0.0498 (6)	0.0425 (5)	0.0458 (5)	−0.0121 (4)	0.0220 (4)	−0.0141 (4)
O2	0.0514 (6)	0.0377 (5)	0.0416 (5)	0.0052 (4)	0.0203 (4)	0.0118 (4)
C1	0.0316 (6)	0.0353 (6)	0.0295 (6)	−0.0033 (5)	0.0092 (5)	−0.0003 (5)
C2	0.0372 (6)	0.0345 (6)	0.0334 (6)	−0.0059 (5)	0.0125 (5)	−0.0022 (5)
C3	0.0348 (6)	0.0366 (7)	0.0327 (6)	−0.0028 (5)	0.0096 (5)	0.0012 (5)
C4	0.0596 (9)	0.0370 (7)	0.0394 (7)	0.0012 (6)	0.0055 (6)	0.0090 (6)
C11	0.0291 (6)	0.0289 (6)	0.0308 (6)	−0.0061 (4)	0.0092 (4)	−0.0028 (5)
C12	0.0347 (6)	0.0288 (6)	0.0317 (6)	−0.0053 (5)	0.0093 (5)	0.0011 (5)
C13	0.0309 (6)	0.0272 (6)	0.0359 (6)	−0.0006 (5)	0.0080 (5)	−0.0006 (5)
C14	0.0283 (6)	0.0271 (6)	0.0313 (6)	−0.0057 (4)	0.0085 (4)	−0.0040 (4)
C15	0.0298 (6)	0.0285 (6)	0.0295 (5)	−0.0044 (5)	0.0094 (4)	−0.0002 (5)
C16	0.0275 (5)	0.0268 (6)	0.0305 (6)	−0.0056 (4)	0.0075 (4)	−0.0033 (4)
C21	0.0305 (6)	0.0228 (5)	0.0351 (6)	−0.0024 (4)	0.0113 (5)	−0.0027 (5)
C22	0.0349 (6)	0.0289 (6)	0.0367 (6)	0.0008 (5)	0.0090 (5)	−0.0008 (5)
C23	0.0310 (6)	0.0302 (6)	0.0534 (8)	0.0008 (5)	0.0129 (6)	−0.0041 (6)
C24	0.0425 (7)	0.0290 (6)	0.0498 (8)	−0.0018 (5)	0.0273 (6)	−0.0070 (5)
C25	0.0493 (8)	0.0382 (7)	0.0348 (6)	0.0004 (6)	0.0163 (6)	−0.0049 (5)
C26	0.0351 (6)	0.0342 (6)	0.0355 (6)	−0.0002 (5)	0.0090 (5)	−0.0046 (5)
C31	0.0286 (6)	0.0287 (6)	0.0260 (5)	−0.0036 (4)	0.0082 (4)	−0.0045 (4)
C32	0.0295 (6)	0.0325 (6)	0.0335 (6)	−0.0035 (5)	0.0109 (5)	−0.0020 (5)
C33	0.0387 (7)	0.0291 (6)	0.0365 (6)	−0.0036 (5)	0.0102 (5)	0.0008 (5)
C34	0.0357 (6)	0.0325 (6)	0.0318 (6)	0.0048 (5)	0.0055 (5)	−0.0028 (5)
C35	0.0270 (6)	0.0419 (7)	0.0376 (6)	−0.0010 (5)	0.0083 (5)	−0.0023 (5)
C36	0.0300 (6)	0.0329 (6)	0.0349 (6)	−0.0057 (5)	0.0090 (5)	−0.0005 (5)
C41	0.0303 (6)	0.0427 (7)	0.0301 (6)	−0.0032 (5)	0.0081 (5)	0.0049 (5)
C42	0.0388 (7)	0.0474 (8)	0.0442 (7)	0.0004 (6)	0.0156 (6)	0.0041 (6)
C43	0.0335 (7)	0.0685 (10)	0.0521 (8)	−0.0030 (7)	0.0164 (6)	0.0089 (8)
C44	0.0392 (7)	0.0645 (10)	0.0459 (8)	−0.0186 (7)	0.0070 (6)	0.0121 (7)
C45	0.0503 (8)	0.0474 (8)	0.0445 (8)	−0.0137 (7)	0.0075 (6)	0.0031 (6)
C46	0.0383 (7)	0.0447 (7)	0.0367 (7)	−0.0048 (6)	0.0106 (5)	0.0014 (6)

F1—C24	1.3648 (14)	C22—H22	0.9500
F2—C34	1.3624 (14)	C23—C24	1.367 (2)
F3—C44	1.3628 (16)	C23—H23	0.9500
O1—C1	1.2180 (15)	C24—C25	1.371 (2)
O2—C12	1.3704 (14)	C25—C26	1.3847 (17)
O2—C4	1.4218 (17)	C25—H25	0.9500
C1—C2	1.4729 (17)	C26—H26	0.9500
C1—C11	1.5070 (16)	C31—C32	1.3936 (16)
C2—C3	1.3278 (17)	C31—C36	1.3981 (16)
C2—H2	0.9500	C32—C33	1.3832 (17)
C3—C41	1.4617 (17)	C32—H32	0.9500
C3—H3	0.9500	C33—C34	1.3741 (18)
C4—H4A	0.9800	C33—H33	0.9500
C4—H4B	0.9800	C34—C35	1.3728 (18)
C4—H4C	0.9800	C35—C36	1.3818 (18)
C11—C12	1.3979 (17)	C35—H35	0.9500
C11—C16	1.4030 (16)	C36—H36	0.9500
C12—C13	1.3849 (17)	C41—C42	1.3925 (18)
C13—C14	1.3954 (17)	C41—C46	1.3974 (19)
C13—H13	0.9500	C42—C43	1.384 (2)
C14—C15	1.3900 (16)	C42—H42	0.9500
C14—C21	1.4859 (15)	C43—C44	1.365 (2)
C15—C16	1.3995 (16)	C43—H43	0.9500
C15—H15	0.9500	C44—C45	1.371 (2)
C16—C31	1.4880 (16)	C45—C46	1.3802 (19)
C21—C26	1.3920 (17)	C45—H45	0.9500
C21—C22	1.3923 (17)	C46—H46	0.9500
C22—C23	1.3836 (18)
C12—O2—C4	117.93 (10)	F1—C24—C25	118.55 (12)
O1—C1—C2	122.93 (11)	C23—C24—C25	123.16 (12)
O1—C1—C11	120.28 (11)	C24—C25—C26	117.86 (12)
C2—C1—C11	116.78 (10)	C24—C25—H25	121.1
C3—C2—C1	121.72 (12)	C26—C25—H25	121.1
C3—C2—H2	119.1	C25—C26—C21	121.26 (12)
C1—C2—H2	119.1	C25—C26—H26	119.4
C2—C3—C41	126.41 (12)	C21—C26—H26	119.4
C2—C3—H3	116.8	C32—C31—C36	117.82 (11)
C41—C3—H3	116.8	C32—C31—C16	119.58 (10)
O2—C4—H4A	109.5	C36—C31—C16	122.59 (10)
O2—C4—H4B	109.5	C33—C32—C31	121.98 (11)
H4A—C4—H4B	109.5	C33—C32—H32	119.0
O2—C4—H4C	109.5	C31—C32—H32	119.0
H4A—C4—H4C	109.5	C34—C33—C32	117.69 (11)
H4B—C4—H4C	109.5	C34—C33—H33	121.2
C12—C11—C16	119.38 (10)	C32—C33—H33	121.2
C12—C11—C1	117.91 (10)	F2—C34—C35	118.87 (11)
C16—C11—C1	122.67 (11)	F2—C34—C33	118.31 (11)
O2—C12—C13	123.54 (11)	C35—C34—C33	122.81 (12)
O2—C12—C11	114.93 (10)	C34—C35—C36	118.60 (11)
C13—C12—C11	121.48 (11)	C34—C35—H35	120.7
C12—C13—C14	119.45 (11)	C36—C35—H35	120.7
C12—C13—H13	120.3	C35—C36—C31	121.05 (11)
C14—C13—H13	120.3	C35—C36—H36	119.5
C15—C14—C13	119.33 (10)	C31—C36—H36	119.5
C15—C14—C21	119.78 (10)	C42—C41—C46	118.44 (12)
C13—C14—C21	120.87 (11)	C42—C41—C3	119.38 (12)
C14—C15—C16	121.73 (11)	C46—C41—C3	122.19 (12)
C14—C15—H15	119.1	C43—C42—C41	121.19 (14)
C16—C15—H15	119.1	C43—C42—H42	119.4
C15—C16—C11	118.53 (11)	C41—C42—H42	119.4
C15—C16—C31	118.53 (10)	C44—C43—C42	117.95 (14)
C11—C16—C31	122.95 (10)	C44—C43—H43	121.0
C26—C21—C22	118.43 (11)	C42—C43—H43	121.0
C26—C21—C14	120.42 (11)	F3—C44—C43	118.54 (14)
C22—C21—C14	121.03 (11)	F3—C44—C45	118.12 (15)
C23—C22—C21	120.96 (12)	C43—C44—C45	123.35 (13)
C23—C22—H22	119.5	C44—C45—C46	118.22 (15)
C21—C22—H22	119.5	C44—C45—H45	120.9
C24—C23—C22	118.31 (12)	C46—C45—H45	120.9
C24—C23—H23	120.8	C45—C46—C41	120.84 (13)
C22—C23—H23	120.8	C45—C46—H46	119.6
F1—C24—C23	118.29 (12)	C41—C46—H46	119.6
O1—C1—C2—C3	−8.7 (2)	C22—C23—C24—C25	1.34 (19)
C11—C1—C2—C3	170.25 (12)	F1—C24—C25—C26	178.35 (11)
C1—C2—C3—C41	−176.55 (12)	C23—C24—C25—C26	−1.3 (2)
O1—C1—C11—C12	−114.77 (14)	C24—C25—C26—C21	0.17 (19)
C2—C1—C11—C12	66.28 (15)	C22—C21—C26—C25	0.88 (18)
O1—C1—C11—C16	62.99 (16)	C14—C21—C26—C25	−175.32 (11)
C2—C1—C11—C16	−115.96 (13)	C15—C16—C31—C32	40.84 (15)
C4—O2—C12—C13	19.08 (18)	C11—C16—C31—C32	−139.22 (12)
C4—O2—C12—C11	−163.68 (11)	C15—C16—C31—C36	−138.15 (12)
C16—C11—C12—O2	179.64 (10)	C11—C16—C31—C36	41.80 (17)
C1—C11—C12—O2	−2.53 (15)	C36—C31—C32—C33	−1.33 (17)
C16—C11—C12—C13	−3.06 (17)	C16—C31—C32—C33	179.63 (11)
C1—C11—C12—C13	174.78 (11)	C31—C32—C33—C34	−0.47 (18)
O2—C12—C13—C14	179.37 (11)	C32—C33—C34—F2	−178.47 (11)
C11—C12—C13—C14	2.30 (18)	C32—C33—C34—C35	1.67 (19)
C12—C13—C14—C15	0.79 (17)	F2—C34—C35—C36	179.18 (11)
C12—C13—C14—C21	−177.28 (11)	C33—C34—C35—C36	−0.96 (19)
C13—C14—C15—C16	−3.16 (17)	C34—C35—C36—C31	−0.97 (18)
C21—C14—C15—C16	174.93 (10)	C32—C31—C36—C35	2.07 (17)
C14—C15—C16—C11	2.39 (17)	C16—C31—C36—C35	−178.93 (11)
C14—C15—C16—C31	−177.66 (10)	C2—C3—C41—C42	167.43 (13)
C12—C11—C16—C15	0.71 (16)	C2—C3—C41—C46	−12.3 (2)
C1—C11—C16—C15	−177.02 (10)	C46—C41—C42—C43	1.2 (2)
C12—C11—C16—C31	−179.24 (10)	C3—C41—C42—C43	−178.53 (13)
C1—C11—C16—C31	3.03 (17)	C41—C42—C43—C44	−0.4 (2)
C15—C14—C21—C26	41.88 (16)	C42—C43—C44—F3	179.40 (13)
C13—C14—C21—C26	−140.05 (12)	C42—C43—C44—C45	−0.5 (2)
C15—C14—C21—C22	−134.22 (12)	F3—C44—C45—C46	−179.36 (13)
C13—C14—C21—C22	43.84 (16)	C43—C44—C45—C46	0.6 (2)
C26—C21—C22—C23	−0.87 (18)	C44—C45—C46—C41	0.3 (2)
C14—C21—C22—C23	175.31 (11)	C42—C41—C46—C45	−1.16 (19)
C21—C22—C23—C24	−0.20 (18)	C3—C41—C46—C45	178.57 (12)
C22—C23—C24—F1	−178.34 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C25—H25···F1i	0.95	2.55	3.2276 (15)	129.
C43—H43···F2ii	0.95	2.53	3.4449 (16)	161.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C25—H25⋯F1i	0.95	2.55	3.2276 (15)	129
C43—H43⋯F2ii	0.95	2.53	3.4449 (16)	161

Symmetry codes: (i) ; (ii) .