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

In the meta-terphenyl fragment of the title mol-ecule, C(29)H(22)F(2)O(2), the two fluoro-phenyl rings are twisted from the central benzene ring by 46.72 (6) and 41.70 (6)°, respectively. In the crystal, weak C-H⋯O and C-H⋯F hydrogen bonds link the mol-ecules into layers parallel to the ab plane. The crystal packing exhibits π-π inter-actions, the shortest distance between the centroids of aromatic rings being 3.6364 (7) Å.

Related literature

For the pharmacological importance of terphenyls, see: Liu (2006 ▶). For our studies of different chalcone derivatives, see: Samshuddin et al. (2011 ▶); Fun et al. (2010 ▶); Jasinski et al. (2010 ▶); Baktir et al. (2011 ▶). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C29H22F2O2

M = 440.47

Triclinic,

a = 6.9020 (3) Å

b = 11.3965 (6) Å

c = 14.8362 (8) Å

α = 96.177 (2)°

β = 93.381 (2)°

γ = 106.446 (2)°

V = 1107.85 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 200 K

0.36 × 0.24 × 0.11 mm

Data collection

Bruker APEXII CCD diffractometer

20122 measured reflections

5516 independent reflections

4020 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.109

S = 1.06

5516 reflections

300 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.24 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/S160053681104579X/cv5183sup1.cif

Supplementary material file. DOI: 10.1107/S160053681104579X/cv5183Isup2.cdx

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681104579X/cv5183Isup3.hkl

Supplementary material file. DOI: 10.1107/S160053681104579X/cv5183Isup4.cml

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

C29H22F2O2	Z = 2
Mr = 440.47	F(000) = 460
Triclinic, P1	Dx = 1.320 Mg m−3
Hall symbol: -P 1	Melting point: 465 K
a = 6.9020 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.3965 (6) Å	Cell parameters from 8632 reflections
c = 14.8362 (8) Å	θ = 2.5–28.3°
α = 96.177 (2)°	µ = 0.09 mm−1
β = 93.381 (2)°	T = 200 K
γ = 106.446 (2)°	Platelet, colourless
V = 1107.85 (10) Å3	0.36 × 0.24 × 0.11 mm

Bruker APEXII CCD diffractometer	4020 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.042
graphite	θmax = 28.4°, θmin = 1.9°
φ and ω scans	h = −9→9
20122 measured reflections	k = −15→15
5516 independent reflections	l = −19→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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0547P)2 + 0.0888P] where P = (Fo2 + 2Fc2)/3
5516 reflections	(Δ/σ)max < 0.001
300 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

	x	y	z	Uiso*/Ueq
F1	−0.32392 (11)	−0.70671 (6)	0.46700 (6)	0.0469 (2)
F2	−0.80404 (14)	0.05047 (10)	0.94895 (6)	0.0661 (3)
O1	−0.20131 (13)	0.21294 (8)	0.70190 (7)	0.0448 (2)
O2	0.19220 (12)	0.09542 (7)	0.60606 (6)	0.0358 (2)
C1	−0.06141 (17)	0.17004 (10)	0.71538 (8)	0.0305 (3)
C2	0.13900 (18)	0.24573 (11)	0.75946 (8)	0.0336 (3)
H2	0.2390	0.2061	0.7733	0.040*
C3	0.18420 (19)	0.36734 (11)	0.78036 (9)	0.0364 (3)
H3	0.0811	0.4041	0.7651	0.044*
C4	0.34886 (17)	0.06610 (12)	0.55736 (9)	0.0376 (3)
H4A	0.4098	0.0142	0.5913	0.056*
H4B	0.4532	0.1424	0.5503	0.056*
H4C	0.2909	0.0216	0.4972	0.056*
C5	0.9333 (2)	0.70099 (15)	0.96324 (12)	0.0630 (5)
H5A	0.9502	0.7847	0.9482	0.095*
H5B	1.0489	0.6733	0.9450	0.095*
H5C	0.9263	0.7008	1.0290	0.095*
C11	−0.08873 (15)	0.03487 (10)	0.68885 (8)	0.0263 (2)
C12	0.04172 (15)	0.00001 (10)	0.62946 (8)	0.0270 (2)
C13	0.01112 (15)	−0.12245 (10)	0.59474 (8)	0.0273 (2)
H13	0.0981	−0.1439	0.5528	0.033*
C14	−0.14791 (15)	−0.21398 (10)	0.62168 (8)	0.0265 (2)
C15	−0.27208 (15)	−0.18035 (10)	0.68396 (8)	0.0273 (2)
H15	−0.3764	−0.2430	0.7045	0.033*
C16	−0.24777 (15)	−0.05737 (10)	0.71708 (8)	0.0260 (2)
C21	−0.18947 (15)	−0.34472 (10)	0.58167 (8)	0.0268 (2)
C22	−0.19231 (16)	−0.37483 (11)	0.48819 (8)	0.0308 (3)
H22	−0.1617	−0.3109	0.4505	0.037*
C23	−0.23905 (16)	−0.49661 (11)	0.44927 (9)	0.0334 (3)
H23	−0.2425	−0.5172	0.3853	0.040*
C24	−0.28010 (16)	−0.58650 (10)	0.50542 (9)	0.0327 (3)
C25	−0.27847 (17)	−0.56188 (11)	0.59813 (9)	0.0354 (3)
H25	−0.3069	−0.6266	0.6351	0.042*
C26	−0.23396 (17)	−0.43962 (11)	0.63608 (9)	0.0318 (3)
H26	−0.2338	−0.4202	0.7000	0.038*
C31	−0.39190 (16)	−0.02834 (10)	0.78062 (8)	0.0279 (2)
C32	−0.32771 (18)	0.05884 (11)	0.85792 (8)	0.0351 (3)
H32	−0.1872	0.1002	0.8720	0.042*
C33	−0.4659 (2)	0.08601 (13)	0.91445 (9)	0.0427 (3)
H33	−0.4220	0.1466	0.9664	0.051*
C34	−0.6676 (2)	0.02359 (13)	0.89374 (10)	0.0425 (3)
C35	−0.73750 (18)	−0.06496 (13)	0.82011 (9)	0.0395 (3)
H35	−0.8780	−0.1077	0.8081	0.047*
C36	−0.59796 (16)	−0.09080 (11)	0.76341 (8)	0.0325 (3)
H36	−0.6438	−0.1521	0.7120	0.039*
C41	0.3765 (2)	0.45038 (11)	0.82446 (9)	0.0373 (3)
C42	0.5431 (2)	0.40945 (13)	0.84736 (11)	0.0496 (4)
H42	0.5346	0.3248	0.8328	0.059*
C43	0.7201 (2)	0.49057 (13)	0.89099 (11)	0.0526 (4)
H43	0.8312	0.4604	0.9061	0.063*
C44	0.7401 (2)	0.61507 (12)	0.91337 (9)	0.0456 (3)
C45	0.5773 (2)	0.65663 (12)	0.88825 (10)	0.0477 (4)
H45	0.5884	0.7419	0.9011	0.057*
C46	0.3984 (2)	0.57627 (12)	0.84473 (10)	0.0435 (3)
H46	0.2889	0.6073	0.8284	0.052*

	U11	U22	U33	U12	U13	U23
F1	0.0460 (4)	0.0236 (4)	0.0651 (6)	0.0042 (3)	0.0076 (4)	−0.0058 (3)
F2	0.0647 (6)	0.0905 (7)	0.0592 (6)	0.0438 (5)	0.0305 (5)	0.0092 (5)
O1	0.0439 (5)	0.0328 (5)	0.0615 (7)	0.0168 (4)	0.0003 (4)	0.0101 (4)
O2	0.0357 (4)	0.0264 (4)	0.0418 (5)	0.0010 (3)	0.0141 (4)	0.0051 (4)
C1	0.0366 (6)	0.0260 (6)	0.0301 (6)	0.0095 (5)	0.0056 (5)	0.0066 (5)
C2	0.0384 (6)	0.0270 (6)	0.0340 (7)	0.0075 (5)	0.0025 (5)	0.0041 (5)
C3	0.0450 (7)	0.0280 (6)	0.0352 (7)	0.0087 (5)	0.0063 (5)	0.0038 (5)
C4	0.0288 (6)	0.0398 (7)	0.0415 (7)	0.0032 (5)	0.0100 (5)	0.0085 (6)
C5	0.0609 (9)	0.0533 (10)	0.0569 (10)	−0.0055 (7)	0.0006 (8)	−0.0081 (8)
C11	0.0274 (5)	0.0243 (5)	0.0264 (6)	0.0067 (4)	−0.0007 (4)	0.0039 (4)
C12	0.0253 (5)	0.0251 (5)	0.0288 (6)	0.0036 (4)	0.0011 (4)	0.0059 (4)
C13	0.0249 (5)	0.0274 (6)	0.0294 (6)	0.0071 (4)	0.0036 (4)	0.0030 (5)
C14	0.0258 (5)	0.0245 (5)	0.0284 (6)	0.0067 (4)	−0.0003 (4)	0.0040 (4)
C15	0.0247 (5)	0.0255 (6)	0.0301 (6)	0.0039 (4)	0.0029 (4)	0.0059 (5)
C16	0.0251 (5)	0.0273 (6)	0.0256 (6)	0.0077 (4)	0.0005 (4)	0.0040 (4)
C21	0.0222 (5)	0.0240 (5)	0.0335 (6)	0.0059 (4)	0.0029 (4)	0.0033 (4)
C22	0.0298 (5)	0.0274 (6)	0.0345 (7)	0.0067 (4)	0.0048 (5)	0.0047 (5)
C23	0.0296 (5)	0.0320 (6)	0.0359 (7)	0.0068 (5)	0.0035 (5)	−0.0015 (5)
C24	0.0248 (5)	0.0224 (6)	0.0481 (8)	0.0049 (4)	0.0034 (5)	−0.0023 (5)
C25	0.0339 (6)	0.0248 (6)	0.0479 (8)	0.0067 (5)	0.0060 (5)	0.0099 (5)
C26	0.0314 (5)	0.0300 (6)	0.0336 (6)	0.0079 (4)	0.0043 (5)	0.0051 (5)
C31	0.0298 (5)	0.0287 (6)	0.0283 (6)	0.0116 (4)	0.0044 (4)	0.0078 (5)
C32	0.0375 (6)	0.0340 (7)	0.0334 (7)	0.0101 (5)	0.0041 (5)	0.0032 (5)
C33	0.0552 (8)	0.0406 (7)	0.0353 (7)	0.0188 (6)	0.0097 (6)	0.0017 (6)
C34	0.0476 (7)	0.0536 (8)	0.0394 (8)	0.0298 (6)	0.0190 (6)	0.0143 (6)
C35	0.0302 (6)	0.0520 (8)	0.0424 (8)	0.0173 (5)	0.0078 (5)	0.0164 (6)
C36	0.0306 (5)	0.0362 (6)	0.0326 (6)	0.0118 (5)	0.0026 (5)	0.0077 (5)
C41	0.0484 (7)	0.0263 (6)	0.0334 (7)	0.0046 (5)	0.0065 (5)	0.0020 (5)
C42	0.0581 (8)	0.0282 (7)	0.0574 (9)	0.0076 (6)	−0.0049 (7)	0.0034 (6)
C43	0.0541 (8)	0.0412 (8)	0.0570 (10)	0.0079 (6)	−0.0068 (7)	0.0056 (7)
C44	0.0540 (8)	0.0378 (8)	0.0347 (7)	−0.0014 (6)	0.0069 (6)	−0.0016 (6)
C45	0.0619 (9)	0.0286 (7)	0.0445 (8)	0.0027 (6)	0.0124 (7)	−0.0061 (6)
C46	0.0535 (8)	0.0299 (7)	0.0448 (8)	0.0095 (6)	0.0098 (6)	−0.0012 (6)

F1—C24	1.3676 (13)	C21—C26	1.3946 (16)
F2—C34	1.3610 (14)	C22—C23	1.3841 (16)
O1—C1	1.2153 (14)	C22—H22	0.9500
O2—C12	1.3660 (12)	C23—C24	1.3678 (17)
O2—C4	1.4310 (14)	C23—H23	0.9500
C1—C2	1.4770 (16)	C24—C25	1.3727 (19)
C1—C11	1.5032 (15)	C25—C26	1.3861 (17)
C2—C3	1.3288 (17)	C25—H25	0.9500
C2—H2	0.9500	C26—H26	0.9500
C3—C41	1.4625 (18)	C31—C36	1.3927 (15)
C3—H3	0.9500	C31—C32	1.3945 (17)
C4—H4A	0.9800	C32—C33	1.3837 (17)
C4—H4B	0.9800	C32—H32	0.9500
C4—H4C	0.9800	C33—C34	1.371 (2)
C5—C44	1.507 (2)	C33—H33	0.9500
C5—H5A	0.9800	C34—C35	1.367 (2)
C5—H5B	0.9800	C35—C36	1.3873 (17)
C5—H5C	0.9800	C35—H35	0.9500
C11—C12	1.4020 (16)	C36—H36	0.9500
C11—C16	1.4075 (15)	C41—C42	1.395 (2)
C12—C13	1.3869 (16)	C41—C46	1.3967 (17)
C13—C14	1.3949 (15)	C42—C43	1.380 (2)
C13—H13	0.9500	C42—H42	0.9500
C14—C15	1.3923 (15)	C43—C44	1.387 (2)
C14—C21	1.4840 (15)	C43—H43	0.9500
C15—C16	1.3938 (15)	C44—C45	1.384 (2)
C15—H15	0.9500	C45—C46	1.3850 (19)
C16—C31	1.4891 (15)	C45—H45	0.9500
C21—C22	1.3900 (17)	C46—H46	0.9500
C12—O2—C4	117.89 (9)	C24—C23—H23	120.9
O1—C1—C2	122.43 (11)	C22—C23—H23	120.9
O1—C1—C11	120.40 (10)	F1—C24—C23	118.13 (11)
C2—C1—C11	117.16 (10)	F1—C24—C25	118.60 (11)
C3—C2—C1	122.25 (11)	C23—C24—C25	123.27 (11)
C3—C2—H2	118.9	C24—C25—C26	117.94 (11)
C1—C2—H2	118.9	C24—C25—H25	121.0
C2—C3—C41	126.60 (12)	C26—C25—H25	121.0
C2—C3—H3	116.7	C25—C26—C21	120.86 (12)
C41—C3—H3	116.7	C25—C26—H26	119.6
O2—C4—H4A	109.5	C21—C26—H26	119.6
O2—C4—H4B	109.5	C36—C31—C32	118.37 (11)
H4A—C4—H4B	109.5	C36—C31—C16	119.36 (10)
O2—C4—H4C	109.5	C32—C31—C16	122.27 (10)
H4A—C4—H4C	109.5	C33—C32—C31	120.91 (11)
H4B—C4—H4C	109.5	C33—C32—H32	119.5
C44—C5—H5A	109.5	C31—C32—H32	119.5
C44—C5—H5B	109.5	C34—C33—C32	118.51 (13)
H5A—C5—H5B	109.5	C34—C33—H33	120.7
C44—C5—H5C	109.5	C32—C33—H33	120.7
H5A—C5—H5C	109.5	F2—C34—C35	118.54 (12)
H5B—C5—H5C	109.5	F2—C34—C33	118.68 (13)
C12—C11—C16	118.99 (10)	C35—C34—C33	122.78 (12)
C12—C11—C1	118.59 (9)	C34—C35—C36	118.27 (11)
C16—C11—C1	122.31 (10)	C34—C35—H35	120.9
O2—C12—C13	123.56 (10)	C36—C35—H35	120.9
O2—C12—C11	115.00 (10)	C35—C36—C31	121.12 (12)
C13—C12—C11	121.37 (9)	C35—C36—H36	119.4
C12—C13—C14	119.73 (10)	C31—C36—H36	119.4
C12—C13—H13	120.1	C42—C41—C46	117.55 (12)
C14—C13—H13	120.1	C42—C41—C3	122.68 (12)
C15—C14—C13	119.07 (10)	C46—C41—C3	119.77 (12)
C15—C14—C21	120.41 (9)	C43—C42—C41	120.74 (13)
C13—C14—C21	120.48 (10)	C43—C42—H42	119.6
C14—C15—C16	121.90 (10)	C41—C42—H42	119.6
C14—C15—H15	119.1	C42—C43—C44	121.73 (15)
C16—C15—H15	119.1	C42—C43—H43	119.1
C15—C16—C11	118.83 (10)	C44—C43—H43	119.1
C15—C16—C31	118.77 (9)	C45—C44—C43	117.65 (13)
C11—C16—C31	122.40 (10)	C45—C44—C5	121.74 (14)
C22—C21—C26	118.81 (11)	C43—C44—C5	120.61 (15)
C22—C21—C14	120.14 (10)	C44—C45—C46	121.26 (13)
C26—C21—C14	121.01 (11)	C44—C45—H45	119.4
C23—C22—C21	120.93 (11)	C46—C45—H45	119.4
C23—C22—H22	119.5	C45—C46—C41	121.02 (14)
C21—C22—H22	119.5	C45—C46—H46	119.5
C24—C23—C22	118.18 (12)	C41—C46—H46	119.5
O1—C1—C2—C3	−5.67 (19)	C22—C23—C24—C25	0.43 (17)
C11—C1—C2—C3	175.54 (11)	F1—C24—C25—C26	−179.95 (10)
C1—C2—C3—C41	179.52 (11)	C23—C24—C25—C26	0.38 (17)
O1—C1—C11—C12	123.37 (12)	C24—C25—C26—C21	−0.90 (17)
C2—C1—C11—C12	−57.82 (14)	C22—C21—C26—C25	0.60 (16)
O1—C1—C11—C16	−52.71 (16)	C14—C21—C26—C25	178.12 (10)
C2—C1—C11—C16	126.10 (11)	C15—C16—C31—C36	−42.03 (15)
C4—O2—C12—C13	−12.40 (16)	C11—C16—C31—C36	137.58 (11)
C4—O2—C12—C11	170.52 (10)	C15—C16—C31—C32	137.28 (12)
C16—C11—C12—O2	−179.66 (10)	C11—C16—C31—C32	−43.11 (16)
C1—C11—C12—O2	4.12 (15)	C36—C31—C32—C33	−2.31 (18)
C16—C11—C12—C13	3.19 (16)	C16—C31—C32—C33	178.38 (11)
C1—C11—C12—C13	−173.03 (10)	C31—C32—C33—C34	1.19 (19)
O2—C12—C13—C14	−179.30 (10)	C32—C33—C34—F2	−179.71 (12)
C11—C12—C13—C14	−2.40 (17)	C32—C33—C34—C35	0.6 (2)
C12—C13—C14—C15	−0.65 (16)	F2—C34—C35—C36	179.17 (11)
C12—C13—C14—C21	176.85 (10)	C33—C34—C35—C36	−1.1 (2)
C13—C14—C15—C16	2.93 (16)	C34—C35—C36—C31	−0.09 (18)
C21—C14—C15—C16	−174.57 (10)	C32—C31—C36—C35	1.75 (17)
C14—C15—C16—C11	−2.12 (16)	C16—C31—C36—C35	−178.91 (11)
C14—C15—C16—C31	177.50 (10)	C2—C3—C41—C42	2.5 (2)
C12—C11—C16—C15	−0.93 (15)	C2—C3—C41—C46	−177.86 (12)
C1—C11—C16—C15	175.14 (10)	C46—C41—C42—C43	2.0 (2)
C12—C11—C16—C31	179.47 (10)	C3—C41—C42—C43	−178.37 (13)
C1—C11—C16—C31	−4.47 (16)	C41—C42—C43—C44	−0.3 (2)
C15—C14—C21—C22	131.87 (11)	C42—C43—C44—C45	−1.7 (2)
C13—C14—C21—C22	−45.60 (15)	C42—C43—C44—C5	178.37 (15)
C15—C14—C21—C26	−45.62 (15)	C43—C44—C45—C46	1.9 (2)
C13—C14—C21—C26	136.91 (11)	C5—C44—C45—C46	−178.15 (13)
C26—C21—C22—C23	0.24 (16)	C44—C45—C46—C41	−0.2 (2)
C14—C21—C22—C23	−177.31 (10)	C42—C41—C46—C45	−1.7 (2)
C21—C22—C23—C24	−0.74 (16)	C3—C41—C46—C45	178.59 (12)
C22—C23—C24—F1	−179.24 (10)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4B···F1i	0.98	2.46	3.3756 (14)	156.
C25—H25···O1ii	0.95	2.43	3.2812 (15)	149.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4B⋯F1i	0.98	2.46	3.3756 (14)	156
C25—H25⋯O1ii	0.95	2.43	3.2812 (15)	149

Symmetry codes: (i) ; (ii) .