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

In the title compound, C28H19BrF2O2, the C=C double bond is E-configured. In the crystal, C-H⋯O and C-H⋯F contacts connect mol-ecules into planes perpendicular to the c axis. The shortest centroid-centroid distance between two aromatic systems is 3.6745 (12) Å between one of the para-fluoro-phenyl rings and its symmetry-generated equivalent.

Related literature

For background to polysubstituted aromatics, see: Astrue (2002 ▶). For the pharmacological properties of terphenyls, see: Liu (2006 ▶). For the crystal structures of various terphenyl chalcones, see: Fun et al. (2012a ▶,b ▶,c ▶,d ▶,e ▶); Betz et al. (2011a ▶,b ▶,c ▶,d ▶,e ▶). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C28H19BrF2O2

M = 505.34

Triclinic,

a = 6.9648 (2) Å

b = 11.3616 (3) Å

c = 14.7219 (4) Å

α = 95.983 (1)°

β = 92.601 (1)°

γ = 105.676 (1)°

V = 1112.23 (5) Å3

Z = 2

Mo Kα radiation

μ = 1.89 mm−1

T = 200 K

0.39 × 0.18 × 0.06 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.843, T max = 1.000

20205 measured reflections

5513 independent reflections

4082 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.089

S = 1.03

5513 reflections

299 parameters

H-atom parameters constrained

Δρmax = 0.52 e Å−3

Δρmin = −0.59 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, 2012 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812046831/kj2214sup1.cif

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812046831/kj2214Isup2.cdx

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812046831/kj2214Isup3.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812046831/kj2214Isup4.cml

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

C28H19BrF2O2	Z = 2
Mr = 505.34	F(000) = 512
Triclinic, P1	Dx = 1.509 Mg m−3
Hall symbol: -P 1	Melting point: 465 K
a = 6.9648 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.3616 (3) Å	Cell parameters from 9095 reflections
c = 14.7219 (4) Å	θ = 2.8–28.1°
α = 95.983 (1)°	µ = 1.89 mm−1
β = 92.601 (1)°	T = 200 K
γ = 105.676 (1)°	Platelet, yellow
V = 1112.23 (5) Å3	0.39 × 0.18 × 0.06 mm

Bruker APEXII CCD diffractometer	5513 independent reflections
Radiation source: fine-focus sealed tube	4082 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
φ and ω scans	θmax = 28.3°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −9→8
Tmin = 0.843, Tmax = 1.000	k = −14→15
20205 measured reflections	l = −14→19

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0367P)2 + 0.5261P] where P = (Fo2 + 2Fc2)/3
5513 reflections	(Δ/σ)max = 0.001
299 parameters	Δρmax = 0.52 e Å−3
0 restraints	Δρmin = −0.59 e Å−3

	x	y	z	Uiso*/Ueq
Br1	1.47038 (4)	0.69865 (2)	0.964665 (19)	0.06360 (11)
F1	0.17425 (18)	−0.70616 (9)	0.46554 (9)	0.0449 (3)
F2	−0.2992 (2)	0.05818 (15)	0.95348 (10)	0.0660 (4)
O1	0.2956 (2)	0.21292 (12)	0.70234 (10)	0.0411 (3)
O2	0.68643 (19)	0.09212 (11)	0.60575 (9)	0.0333 (3)
C1	0.4330 (3)	0.16804 (16)	0.71582 (12)	0.0283 (4)
C2	0.6299 (3)	0.24098 (16)	0.75928 (12)	0.0311 (4)
H2	0.7276	0.1995	0.7724	0.037*
C3	0.6763 (3)	0.36236 (17)	0.78083 (13)	0.0333 (4)
H3	0.5760	0.4015	0.7668	0.040*
C4	0.8438 (3)	0.06260 (18)	0.55674 (13)	0.0354 (4)
H4A	0.9021	0.0090	0.5905	0.053*
H4B	0.9473	0.1386	0.5504	0.053*
H4C	0.7895	0.0200	0.4959	0.053*
C11	0.4061 (2)	0.03293 (15)	0.68905 (11)	0.0241 (3)
C12	0.5376 (2)	−0.00254 (15)	0.62941 (11)	0.0254 (3)
C13	0.5083 (2)	−0.12487 (15)	0.59477 (11)	0.0256 (3)
H13	0.5959	−0.1470	0.5528	0.031*
C14	0.3504 (3)	−0.21496 (15)	0.62163 (11)	0.0247 (3)
C15	0.2252 (3)	−0.18096 (15)	0.68441 (11)	0.0256 (3)
H15	0.1212	−0.2430	0.7050	0.031*
C16	0.2490 (2)	−0.05819 (15)	0.71756 (11)	0.0242 (3)
C21	0.3091 (2)	−0.34537 (15)	0.58143 (12)	0.0250 (3)
C22	0.3101 (3)	−0.37450 (16)	0.48739 (12)	0.0294 (4)
H22	0.3429	−0.3102	0.4495	0.035*
C23	0.2639 (3)	−0.49584 (17)	0.44818 (13)	0.0318 (4)
H23	0.2635	−0.5156	0.3838	0.038*
C24	0.2190 (3)	−0.58645 (16)	0.50428 (14)	0.0318 (4)
C25	0.2171 (3)	−0.56276 (17)	0.59744 (14)	0.0339 (4)
H25	0.1863	−0.6279	0.6346	0.041*
C26	0.2615 (3)	−0.44072 (16)	0.63582 (13)	0.0307 (4)
H26	0.2594	−0.4220	0.7001	0.037*
C31	0.1056 (3)	−0.02790 (16)	0.78209 (11)	0.0260 (3)
C32	−0.0973 (3)	−0.08727 (18)	0.76598 (12)	0.0313 (4)
H32	−0.1427	−0.1480	0.7145	0.038*
C33	−0.2352 (3)	−0.0592 (2)	0.82402 (14)	0.0389 (5)
H33	−0.3738	−0.1002	0.8130	0.047*
C34	−0.1653 (3)	0.0291 (2)	0.89732 (14)	0.0422 (5)
C35	0.0336 (3)	0.08800 (19)	0.91716 (14)	0.0422 (5)
H35	0.0773	0.1478	0.9693	0.051*
C36	0.1697 (3)	0.05844 (17)	0.85951 (12)	0.0327 (4)
H36	0.3085	0.0975	0.8729	0.039*
C41	0.8670 (3)	0.44118 (16)	0.82402 (13)	0.0337 (4)
C42	0.8910 (3)	0.56700 (18)	0.84722 (15)	0.0420 (5)
H42	0.7831	0.6004	0.8341	0.050*
C43	1.0695 (3)	0.64393 (19)	0.88910 (15)	0.0463 (5)
H43	1.0842	0.7294	0.9045	0.056*
C44	1.2251 (3)	0.59503 (19)	0.90813 (13)	0.0406 (5)
C45	1.2077 (4)	0.4715 (2)	0.88436 (16)	0.0467 (5)
H45	1.3171	0.4390	0.8968	0.056*
C46	1.0300 (3)	0.39593 (18)	0.84251 (15)	0.0432 (5)
H46	1.0182	0.3111	0.8259	0.052*

	U11	U22	U33	U12	U13	U23
Br1	0.05179 (16)	0.05650 (17)	0.06461 (17)	−0.00644 (11)	−0.00125 (12)	−0.01426 (12)
F1	0.0442 (7)	0.0223 (5)	0.0631 (8)	0.0047 (5)	0.0065 (6)	−0.0069 (5)
F2	0.0665 (9)	0.0897 (11)	0.0614 (9)	0.0480 (8)	0.0353 (7)	0.0150 (8)
O1	0.0397 (8)	0.0304 (7)	0.0576 (9)	0.0162 (6)	0.0013 (7)	0.0093 (6)
O2	0.0317 (7)	0.0250 (6)	0.0404 (7)	0.0014 (5)	0.0131 (6)	0.0045 (5)
C1	0.0344 (10)	0.0236 (8)	0.0288 (8)	0.0095 (7)	0.0055 (7)	0.0064 (7)
C2	0.0360 (10)	0.0258 (9)	0.0319 (9)	0.0092 (7)	0.0016 (8)	0.0041 (7)
C3	0.0382 (10)	0.0275 (9)	0.0346 (9)	0.0094 (8)	0.0059 (8)	0.0027 (7)
C4	0.0262 (9)	0.0389 (10)	0.0394 (10)	0.0038 (8)	0.0102 (8)	0.0072 (8)
C11	0.0248 (8)	0.0231 (8)	0.0252 (8)	0.0081 (7)	−0.0006 (6)	0.0032 (6)
C12	0.0231 (8)	0.0250 (8)	0.0275 (8)	0.0046 (7)	0.0025 (7)	0.0055 (7)
C13	0.0240 (8)	0.0261 (8)	0.0275 (8)	0.0078 (7)	0.0041 (7)	0.0030 (7)
C14	0.0256 (8)	0.0235 (8)	0.0253 (8)	0.0076 (7)	−0.0005 (6)	0.0032 (6)
C15	0.0235 (8)	0.0249 (8)	0.0282 (8)	0.0054 (7)	0.0031 (6)	0.0048 (7)
C16	0.0233 (8)	0.0266 (8)	0.0236 (8)	0.0084 (7)	0.0002 (6)	0.0039 (6)
C21	0.0202 (8)	0.0231 (8)	0.0316 (9)	0.0062 (6)	0.0020 (7)	0.0024 (7)
C22	0.0285 (9)	0.0264 (9)	0.0326 (9)	0.0063 (7)	0.0033 (7)	0.0038 (7)
C23	0.0309 (9)	0.0303 (9)	0.0320 (9)	0.0073 (7)	0.0030 (7)	−0.0033 (7)
C24	0.0241 (9)	0.0219 (8)	0.0472 (11)	0.0054 (7)	0.0023 (8)	−0.0033 (8)
C25	0.0326 (10)	0.0250 (9)	0.0457 (11)	0.0078 (7)	0.0063 (8)	0.0099 (8)
C26	0.0322 (10)	0.0287 (9)	0.0320 (9)	0.0092 (7)	0.0040 (7)	0.0046 (7)
C31	0.0281 (9)	0.0265 (8)	0.0272 (8)	0.0121 (7)	0.0048 (7)	0.0077 (7)
C32	0.0299 (9)	0.0355 (10)	0.0313 (9)	0.0120 (8)	0.0039 (7)	0.0087 (8)
C33	0.0287 (10)	0.0533 (12)	0.0430 (11)	0.0187 (9)	0.0092 (8)	0.0211 (10)
C34	0.0500 (13)	0.0532 (13)	0.0381 (11)	0.0324 (11)	0.0210 (9)	0.0163 (9)
C35	0.0570 (14)	0.0402 (11)	0.0345 (10)	0.0211 (10)	0.0131 (9)	0.0026 (9)
C36	0.0364 (10)	0.0319 (9)	0.0306 (9)	0.0104 (8)	0.0050 (8)	0.0041 (7)
C41	0.0426 (11)	0.0245 (9)	0.0315 (9)	0.0051 (8)	0.0065 (8)	0.0021 (7)
C42	0.0468 (12)	0.0283 (10)	0.0494 (12)	0.0105 (9)	0.0081 (9)	−0.0047 (9)
C43	0.0547 (13)	0.0285 (10)	0.0483 (12)	0.0038 (9)	0.0129 (10)	−0.0122 (9)
C44	0.0436 (12)	0.0374 (11)	0.0325 (10)	−0.0005 (9)	0.0052 (8)	−0.0030 (8)
C45	0.0477 (13)	0.0373 (11)	0.0528 (13)	0.0079 (10)	−0.0022 (10)	0.0077 (10)
C46	0.0491 (12)	0.0233 (9)	0.0537 (13)	0.0063 (9)	−0.0039 (10)	0.0024 (9)

Br1—C44	1.891 (2)	C22—H22	0.9500
F1—C24	1.3657 (19)	C23—C24	1.366 (3)
F2—C34	1.357 (2)	C23—H23	0.9500
O1—C1	1.217 (2)	C24—C25	1.371 (3)
O2—C12	1.364 (2)	C25—C26	1.388 (2)
O2—C4	1.433 (2)	C25—H25	0.9500
C1—C2	1.474 (3)	C26—H26	0.9500
C1—C11	1.503 (2)	C31—C32	1.389 (3)
C2—C3	1.329 (3)	C31—C36	1.395 (2)
C2—H2	0.9500	C32—C33	1.392 (3)
C3—C41	1.460 (3)	C32—H32	0.9500
C3—H3	0.9500	C33—C34	1.368 (3)
C4—H4A	0.9800	C33—H33	0.9500
C4—H4B	0.9800	C34—C35	1.369 (3)
C4—H4C	0.9800	C35—C36	1.385 (3)
C11—C16	1.402 (2)	C35—H35	0.9500
C11—C12	1.404 (2)	C36—H36	0.9500
C12—C13	1.387 (2)	C41—C46	1.394 (3)
C13—C14	1.389 (2)	C41—C42	1.397 (3)
C13—H13	0.9500	C42—C43	1.386 (3)
C14—C15	1.395 (2)	C42—H42	0.9500
C14—C21	1.483 (2)	C43—C44	1.376 (3)
C15—C16	1.392 (2)	C43—H43	0.9500
C15—H15	0.9500	C44—C45	1.382 (3)
C16—C31	1.491 (2)	C45—C46	1.376 (3)
C21—C22	1.390 (2)	C45—H45	0.9500
C21—C26	1.391 (2)	C46—H46	0.9500
C22—C23	1.384 (2)
C12—O2—C4	118.13 (14)	F1—C24—C25	118.62 (17)
O1—C1—C2	122.64 (16)	C23—C24—C25	123.09 (16)
O1—C1—C11	120.39 (16)	C24—C25—C26	118.00 (17)
C2—C1—C11	116.97 (15)	C24—C25—H25	121.0
C3—C2—C1	122.68 (18)	C26—C25—H25	121.0
C3—C2—H2	118.7	C25—C26—C21	120.92 (17)
C1—C2—H2	118.7	C25—C26—H26	119.5
C2—C3—C41	126.11 (19)	C21—C26—H26	119.5
C2—C3—H3	116.9	C32—C31—C36	118.52 (16)
C41—C3—H3	116.9	C32—C31—C16	119.79 (15)
O2—C4—H4A	109.5	C36—C31—C16	121.69 (16)
O2—C4—H4B	109.5	C31—C32—C33	121.10 (18)
H4A—C4—H4B	109.5	C31—C32—H32	119.5
O2—C4—H4C	109.5	C33—C32—H32	119.5
H4A—C4—H4C	109.5	C34—C33—C32	118.06 (19)
H4B—C4—H4C	109.5	C34—C33—H33	121.0
C16—C11—C12	119.02 (15)	C32—C33—H33	121.0
C16—C11—C1	122.48 (15)	F2—C34—C33	118.4 (2)
C12—C11—C1	118.42 (15)	F2—C34—C35	118.7 (2)
O2—C12—C13	123.84 (15)	C33—C34—C35	122.91 (18)
O2—C12—C11	114.96 (15)	C34—C35—C36	118.53 (19)
C13—C12—C11	121.13 (15)	C34—C35—H35	120.7
C12—C13—C14	119.82 (15)	C36—C35—H35	120.7
C12—C13—H13	120.1	C35—C36—C31	120.82 (19)
C14—C13—H13	120.1	C35—C36—H36	119.6
C13—C14—C15	119.27 (15)	C31—C36—H36	119.6
C13—C14—C21	120.73 (15)	C46—C41—C42	117.83 (19)
C15—C14—C21	119.95 (15)	C46—C41—C3	122.37 (17)
C16—C15—C14	121.53 (16)	C42—C41—C3	119.79 (19)
C16—C15—H15	119.2	C43—C42—C41	121.1 (2)
C14—C15—H15	119.2	C43—C42—H42	119.4
C15—C16—C11	119.11 (15)	C41—C42—H42	119.4
C15—C16—C31	118.76 (15)	C44—C43—C42	119.18 (19)
C11—C16—C31	122.13 (15)	C44—C43—H43	120.4
C22—C21—C26	118.73 (16)	C42—C43—H43	120.4
C22—C21—C14	120.05 (15)	C43—C44—C45	121.1 (2)
C26—C21—C14	121.18 (15)	C43—C44—Br1	119.81 (15)
C23—C22—C21	120.91 (17)	C45—C44—Br1	119.05 (17)
C23—C22—H22	119.5	C46—C45—C44	119.2 (2)
C21—C22—H22	119.5	C46—C45—H45	120.4
C24—C23—C22	118.35 (17)	C44—C45—H45	120.4
C24—C23—H23	120.8	C45—C46—C41	121.47 (19)
C22—C23—H23	120.8	C45—C46—H46	119.3
F1—C24—C23	118.30 (17)	C41—C46—H46	119.3
O1—C1—C2—C3	−5.0 (3)	C22—C23—C24—C25	0.1 (3)
C11—C1—C2—C3	175.70 (17)	F1—C24—C25—C26	−179.59 (16)
C1—C2—C3—C41	179.87 (17)	C23—C24—C25—C26	0.6 (3)
O1—C1—C11—C16	−53.0 (2)	C24—C25—C26—C21	−0.8 (3)
C2—C1—C11—C16	126.29 (18)	C22—C21—C26—C25	0.4 (3)
O1—C1—C11—C12	123.62 (19)	C14—C21—C26—C25	178.02 (16)
C2—C1—C11—C12	−57.1 (2)	C15—C16—C31—C32	−42.3 (2)
C4—O2—C12—C13	−12.6 (3)	C11—C16—C31—C32	137.48 (18)
C4—O2—C12—C11	170.62 (15)	C15—C16—C31—C36	137.16 (18)
C16—C11—C12—O2	−179.64 (15)	C11—C16—C31—C36	−43.1 (2)
C1—C11—C12—O2	3.6 (2)	C36—C31—C32—C33	1.8 (3)
C16—C11—C12—C13	3.4 (3)	C16—C31—C32—C33	−178.73 (16)
C1—C11—C12—C13	−173.33 (16)	C31—C32—C33—C34	0.3 (3)
O2—C12—C13—C14	−178.88 (16)	C32—C33—C34—F2	179.10 (17)
C11—C12—C13—C14	−2.2 (3)	C32—C33—C34—C35	−1.9 (3)
C12—C13—C14—C15	−1.0 (3)	F2—C34—C35—C36	−179.76 (18)
C12—C13—C14—C21	176.46 (16)	C33—C34—C35—C36	1.2 (3)
C13—C14—C15—C16	3.0 (3)	C34—C35—C36—C31	1.0 (3)
C21—C14—C15—C16	−174.42 (16)	C32—C31—C36—C35	−2.5 (3)
C14—C15—C16—C11	−1.8 (3)	C16—C31—C36—C35	178.06 (17)
C14—C15—C16—C31	177.93 (16)	C2—C3—C41—C46	4.2 (3)
C12—C11—C16—C15	−1.4 (2)	C2—C3—C41—C42	−176.57 (19)
C1—C11—C16—C15	175.23 (16)	C46—C41—C42—C43	−1.4 (3)
C12—C11—C16—C31	178.87 (15)	C3—C41—C42—C43	179.34 (19)
C1—C11—C16—C31	−4.5 (3)	C41—C42—C43—C44	−0.1 (3)
C13—C14—C21—C22	−45.3 (2)	C42—C43—C44—C45	1.5 (3)
C15—C14—C21—C22	132.09 (18)	C42—C43—C44—Br1	179.66 (16)
C13—C14—C21—C26	137.12 (18)	C43—C44—C45—C46	−1.2 (3)
C15—C14—C21—C26	−45.5 (2)	Br1—C44—C45—C46	−179.46 (17)
C26—C21—C22—C23	0.3 (3)	C44—C45—C46—C41	−0.3 (3)
C14—C21—C22—C23	−177.33 (16)	C42—C41—C46—C45	1.6 (3)
C21—C22—C23—C24	−0.6 (3)	C3—C41—C46—C45	−179.13 (19)
C22—C23—C24—F1	−179.72 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4B···F1i	0.98	2.51	3.428 (2)	156
C25—H25···O1ii	0.95	2.43	3.268 (2)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4B⋯F1i	0.98	2.51	3.428 (2)	156
C25—H25⋯O1ii	0.95	2.43	3.268 (2)	147

Symmetry codes: (i) ; (ii) .