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

The title compound, C(28)H(20)F(2)O(2), is a polysubstituted terphenyl derivative bearing a Michael system. The C=C double bond is E configured. In the crystal, C-H⋯O and C-H⋯F contacts connect the mol-ecules, forming undulating sheets that lie perpendicular to the crystallographic a axis. The shortest π-π inter-action [centroid-centroid distance = 3.7163 (7) Å] involves the para-fluoro-phenyl ring in the para position 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 our work on the synthesis of different derivatives of chalcones, see: Samshuddin et al. (2011a ▶,b ▶); Fun et al. (2010a ▶,b ▶); Jasinski et al. (2010a ▶,b ▶); Baktır et al. (2011a ▶,b ▶). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C28H20F2O2

M = 426.44

Monoclinic,

a = 13.9226 (4) Å

b = 6.7977 (2) Å

c = 22.4531 (7) Å

β = 101.874 (1)°

V = 2079.53 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 200 K

0.48 × 0.13 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer

19250 measured reflections

5125 independent reflections

3527 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.094

S = 1.01

5125 reflections

290 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.21 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/S1600536811045375/su2328sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811045375/su2328Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811045375/su2328Isup3.cdx

Supplementary material file. DOI: 10.1107/S1600536811045375/su2328Isup4.cml

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

C28H20F2O2	F(000) = 888
Mr = 426.44	Dx = 1.362 Mg m−3
Monoclinic, P21/c	Melting point: 423 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 13.9226 (4) Å	Cell parameters from 7468 reflections
b = 6.7977 (2) Å	θ = 2.6–28.0°
c = 22.4531 (7) Å	µ = 0.10 mm−1
β = 101.874 (1)°	T = 200 K
V = 2079.53 (11) Å3	Platelet, colourless
Z = 4	0.48 × 0.13 × 0.10 mm

Bruker APEXII CCD diffractometer	3527 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.040
graphite	θmax = 28.3°, θmin = 1.9°
φ and ω scans	h = −18→17
19250 measured reflections	k = −8→9
5125 independent reflections	l = −25→29

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0511P)2] where P = (Fo2 + 2Fc2)/3
5125 reflections	(Δ/σ)max < 0.001
290 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

	x	y	z	Uiso*/Ueq
F1	−0.03088 (6)	0.94826 (11)	−0.35137 (3)	0.0494 (2)
F2	0.50301 (6)	0.12071 (11)	0.05515 (3)	0.0493 (2)
O1	0.21900 (6)	0.67802 (12)	0.11362 (4)	0.0394 (2)
O2	0.11107 (6)	1.12741 (12)	0.04508 (4)	0.0353 (2)
C1	0.23288 (8)	0.83556 (17)	0.09109 (5)	0.0270 (3)
C2	0.27709 (8)	1.00565 (17)	0.12773 (5)	0.0300 (3)
H2	0.2950	1.1175	0.1071	0.036*
C3	0.29307 (8)	1.00990 (18)	0.18816 (5)	0.0310 (3)
H3	0.2748	0.8965	0.2079	0.037*
C4	0.06138 (9)	1.30889 (18)	0.02758 (6)	0.0368 (3)
H4A	−0.0034	1.2818	0.0022	0.055*
H4B	0.0999	1.3881	0.0045	0.055*
H4C	0.0536	1.3812	0.0641	0.055*
C11	0.20575 (8)	0.86471 (16)	0.02319 (5)	0.0238 (2)
C12	0.13992 (8)	1.01639 (16)	0.00102 (5)	0.0257 (2)
C13	0.10403 (8)	1.04127 (16)	−0.06077 (5)	0.0267 (2)
H13	0.0582	1.1431	−0.0749	0.032*
C14	0.13529 (8)	0.91667 (16)	−0.10215 (5)	0.0253 (2)
C15	0.20392 (8)	0.77097 (16)	−0.08044 (5)	0.0260 (2)
H15	0.2276	0.6901	−0.1088	0.031*
C16	0.23890 (8)	0.74032 (15)	−0.01843 (5)	0.0239 (2)
C21	0.09231 (8)	0.93258 (16)	−0.16842 (5)	0.0259 (2)
C22	−0.00938 (8)	0.94150 (16)	−0.18843 (5)	0.0297 (3)
H22	−0.0506	0.9446	−0.1596	0.036*
C23	−0.05075 (9)	0.94585 (17)	−0.25003 (6)	0.0327 (3)
H23	−0.1200	0.9496	−0.2638	0.039*
C24	0.01025 (10)	0.94466 (17)	−0.29052 (5)	0.0331 (3)
C25	0.11065 (10)	0.93945 (18)	−0.27319 (6)	0.0353 (3)
H25	0.1510	0.9410	−0.3025	0.042*
C26	0.15114 (9)	0.93183 (17)	−0.21152 (5)	0.0311 (3)
H26	0.2204	0.9260	−0.1984	0.037*
C31	0.31015 (8)	0.57820 (16)	0.00173 (5)	0.0243 (2)
C32	0.29576 (8)	0.39510 (16)	−0.02707 (5)	0.0279 (3)
H32	0.2405	0.3764	−0.0593	0.033*
C33	0.36021 (9)	0.24029 (17)	−0.00969 (5)	0.0308 (3)
H33	0.3498	0.1162	−0.0294	0.037*
C34	0.43955 (9)	0.27162 (17)	0.03683 (5)	0.0317 (3)
C35	0.45767 (9)	0.44935 (18)	0.06604 (5)	0.0319 (3)
H35	0.5135	0.4667	0.0980	0.038*
C36	0.39282 (8)	0.60273 (17)	0.04799 (5)	0.0273 (3)
H36	0.4049	0.7269	0.0675	0.033*
C41	0.33623 (8)	1.17345 (18)	0.22707 (5)	0.0298 (3)
C42	0.35335 (9)	1.1541 (2)	0.29036 (5)	0.0372 (3)
H42	0.3345	1.0366	0.3078	0.045*
C43	0.39754 (9)	1.3043 (2)	0.32801 (6)	0.0431 (3)
H43	0.4086	1.2890	0.3709	0.052*
C44	0.42550 (9)	1.4751 (2)	0.30357 (6)	0.0431 (3)
H44	0.4572	1.5765	0.3295	0.052*
C45	0.40733 (9)	1.4990 (2)	0.24114 (6)	0.0415 (3)
H45	0.4256	1.6178	0.2241	0.050*
C46	0.36256 (9)	1.35020 (19)	0.20337 (6)	0.0364 (3)
H46	0.3495	1.3688	0.1605	0.044*

	U11	U22	U33	U12	U13	U23
F1	0.0717 (5)	0.0466 (5)	0.0227 (4)	0.0038 (4)	−0.0068 (4)	−0.0007 (3)
F2	0.0611 (5)	0.0429 (4)	0.0427 (5)	0.0271 (4)	0.0080 (4)	0.0095 (4)
O1	0.0557 (5)	0.0331 (5)	0.0312 (5)	−0.0031 (4)	0.0136 (4)	0.0058 (4)
O2	0.0426 (5)	0.0358 (5)	0.0272 (5)	0.0140 (4)	0.0067 (4)	−0.0025 (4)
C1	0.0259 (6)	0.0309 (6)	0.0255 (6)	0.0033 (5)	0.0079 (5)	0.0025 (5)
C2	0.0318 (6)	0.0336 (6)	0.0243 (6)	−0.0018 (5)	0.0047 (5)	0.0014 (5)
C3	0.0325 (6)	0.0347 (7)	0.0255 (6)	0.0022 (5)	0.0054 (5)	0.0037 (5)
C4	0.0400 (7)	0.0283 (6)	0.0429 (8)	0.0077 (5)	0.0100 (6)	−0.0037 (5)
C11	0.0248 (5)	0.0233 (5)	0.0225 (6)	−0.0028 (4)	0.0029 (4)	0.0001 (4)
C12	0.0271 (6)	0.0239 (6)	0.0260 (6)	−0.0015 (4)	0.0055 (5)	−0.0031 (5)
C13	0.0268 (6)	0.0236 (6)	0.0285 (6)	0.0016 (5)	0.0026 (5)	0.0016 (5)
C14	0.0259 (5)	0.0241 (6)	0.0244 (6)	−0.0033 (4)	0.0020 (5)	0.0005 (5)
C15	0.0271 (6)	0.0255 (6)	0.0248 (6)	−0.0006 (4)	0.0046 (5)	−0.0040 (5)
C16	0.0227 (5)	0.0217 (5)	0.0265 (6)	−0.0022 (4)	0.0032 (5)	−0.0002 (5)
C21	0.0310 (6)	0.0207 (5)	0.0242 (6)	−0.0009 (5)	0.0019 (5)	−0.0005 (4)
C22	0.0319 (6)	0.0273 (6)	0.0287 (6)	0.0017 (5)	0.0037 (5)	0.0008 (5)
C23	0.0333 (6)	0.0285 (6)	0.0318 (7)	0.0019 (5)	−0.0038 (5)	−0.0002 (5)
C24	0.0504 (8)	0.0235 (6)	0.0209 (6)	0.0016 (5)	−0.0034 (6)	0.0001 (5)
C25	0.0482 (8)	0.0315 (6)	0.0279 (7)	0.0009 (6)	0.0115 (6)	−0.0006 (5)
C26	0.0310 (6)	0.0312 (6)	0.0300 (7)	−0.0007 (5)	0.0040 (5)	−0.0018 (5)
C31	0.0250 (5)	0.0252 (6)	0.0236 (6)	0.0008 (4)	0.0073 (5)	0.0025 (4)
C32	0.0283 (6)	0.0276 (6)	0.0278 (6)	−0.0015 (5)	0.0060 (5)	−0.0003 (5)
C33	0.0390 (7)	0.0242 (6)	0.0321 (7)	0.0000 (5)	0.0139 (6)	−0.0002 (5)
C34	0.0371 (6)	0.0311 (6)	0.0296 (7)	0.0126 (5)	0.0129 (5)	0.0098 (5)
C35	0.0296 (6)	0.0396 (7)	0.0252 (6)	0.0042 (5)	0.0024 (5)	0.0031 (5)
C36	0.0296 (6)	0.0269 (6)	0.0252 (6)	0.0004 (5)	0.0051 (5)	−0.0009 (5)
C41	0.0271 (6)	0.0391 (7)	0.0222 (6)	0.0049 (5)	0.0028 (5)	−0.0009 (5)
C42	0.0399 (7)	0.0448 (8)	0.0257 (7)	0.0043 (6)	0.0041 (6)	0.0036 (6)
C43	0.0429 (7)	0.0596 (9)	0.0235 (7)	0.0066 (7)	−0.0005 (6)	−0.0054 (6)
C44	0.0379 (7)	0.0505 (9)	0.0377 (8)	−0.0004 (6)	0.0002 (6)	−0.0130 (6)
C45	0.0423 (7)	0.0415 (8)	0.0414 (8)	−0.0054 (6)	0.0098 (6)	−0.0032 (6)
C46	0.0415 (7)	0.0430 (7)	0.0243 (6)	−0.0015 (6)	0.0056 (5)	−0.0003 (5)

F1—C24	1.3687 (13)	C23—C24	1.3658 (18)
F2—C34	1.3611 (13)	C23—H23	0.9500
O1—C1	1.2167 (14)	C24—C25	1.3722 (18)
O2—C12	1.3687 (13)	C25—C26	1.3843 (16)
O2—C4	1.4294 (14)	C25—H25	0.9500
C1—C2	1.4779 (16)	C26—H26	0.9500
C1—C11	1.5064 (15)	C31—C36	1.3926 (15)
C2—C3	1.3292 (16)	C31—C32	1.3980 (15)
C2—H2	0.9500	C32—C33	1.3860 (16)
C3—C41	1.4644 (17)	C32—H32	0.9500
C3—H3	0.9500	C33—C34	1.3719 (17)
C4—H4A	0.9800	C33—H33	0.9500
C4—H4B	0.9800	C34—C35	1.3730 (17)
C4—H4C	0.9800	C35—C36	1.3841 (16)
C11—C12	1.4012 (15)	C35—H35	0.9500
C11—C16	1.4065 (15)	C36—H36	0.9500
C12—C13	1.3849 (16)	C41—C46	1.3933 (17)
C13—C14	1.3915 (15)	C41—C42	1.3981 (16)
C13—H13	0.9500	C42—C43	1.3860 (18)
C14—C15	1.3928 (15)	C42—H42	0.9500
C14—C21	1.4893 (15)	C43—C44	1.375 (2)
C15—C16	1.3930 (15)	C43—H43	0.9500
C15—H15	0.9500	C44—C45	1.3819 (19)
C16—C31	1.4895 (15)	C44—H44	0.9500
C21—C26	1.3905 (16)	C45—C46	1.3832 (18)
C21—C22	1.3958 (15)	C45—H45	0.9500
C22—C23	1.3848 (16)	C46—H46	0.9500
C22—H22	0.9500
C12—O2—C4	118.33 (9)	C23—C24—C25	123.23 (11)
O1—C1—C2	122.73 (11)	F1—C24—C25	118.43 (11)
O1—C1—C11	120.56 (10)	C24—C25—C26	117.78 (12)
C2—C1—C11	116.71 (10)	C24—C25—H25	121.1
C3—C2—C1	123.25 (11)	C26—C25—H25	121.1
C3—C2—H2	118.4	C25—C26—C21	121.26 (11)
C1—C2—H2	118.4	C25—C26—H26	119.4
C2—C3—C41	125.97 (11)	C21—C26—H26	119.4
C2—C3—H3	117.0	C36—C31—C32	118.00 (10)
C41—C3—H3	117.0	C36—C31—C16	122.32 (10)
O2—C4—H4A	109.5	C32—C31—C16	119.67 (10)
O2—C4—H4B	109.5	C33—C32—C31	121.53 (11)
H4A—C4—H4B	109.5	C33—C32—H32	119.2
O2—C4—H4C	109.5	C31—C32—H32	119.2
H4A—C4—H4C	109.5	C34—C33—C32	118.02 (11)
H4B—C4—H4C	109.5	C34—C33—H33	121.0
C12—C11—C16	119.11 (10)	C32—C33—H33	121.0
C12—C11—C1	117.76 (10)	F2—C34—C33	118.94 (10)
C16—C11—C1	123.03 (10)	F2—C34—C35	118.35 (11)
O2—C12—C13	123.90 (10)	C33—C34—C35	122.70 (10)
O2—C12—C11	114.63 (10)	C34—C35—C36	118.58 (11)
C13—C12—C11	121.37 (10)	C34—C35—H35	120.7
C12—C13—C14	119.77 (10)	C36—C35—H35	120.7
C12—C13—H13	120.1	C35—C36—C31	121.16 (11)
C14—C13—H13	120.1	C35—C36—H36	119.4
C13—C14—C15	119.05 (10)	C31—C36—H36	119.4
C13—C14—C21	120.42 (10)	C46—C41—C42	117.78 (11)
C15—C14—C21	120.46 (10)	C46—C41—C3	122.33 (11)
C14—C15—C16	121.98 (10)	C42—C41—C3	119.88 (11)
C14—C15—H15	119.0	C43—C42—C41	120.80 (12)
C16—C15—H15	119.0	C43—C42—H42	119.6
C15—C16—C11	118.62 (10)	C41—C42—H42	119.6
C15—C16—C31	119.24 (10)	C44—C43—C42	120.37 (12)
C11—C16—C31	122.14 (10)	C44—C43—H43	119.8
C26—C21—C22	118.68 (10)	C42—C43—H43	119.8
C26—C21—C14	121.47 (10)	C43—C44—C45	119.75 (12)
C22—C21—C14	119.81 (10)	C43—C44—H44	120.1
C23—C22—C21	120.55 (11)	C45—C44—H44	120.1
C23—C22—H22	119.7	C44—C45—C46	120.10 (13)
C21—C22—H22	119.7	C44—C45—H45	119.9
C24—C23—C22	118.47 (11)	C46—C45—H45	119.9
C24—C23—H23	120.8	C45—C46—C41	121.14 (12)
C22—C23—H23	120.8	C45—C46—H46	119.4
C23—C24—F1	118.33 (11)	C41—C46—H46	119.4
O1—C1—C2—C3	−9.33 (18)	C22—C23—C24—F1	179.77 (10)
C11—C1—C2—C3	171.15 (11)	C22—C23—C24—C25	−0.04 (18)
C1—C2—C3—C41	−179.84 (10)	C23—C24—C25—C26	1.09 (18)
O1—C1—C11—C12	122.58 (12)	F1—C24—C25—C26	−178.72 (10)
C2—C1—C11—C12	−57.89 (13)	C24—C25—C26—C21	−1.01 (18)
O1—C1—C11—C16	−53.63 (15)	C22—C21—C26—C25	−0.09 (17)
C2—C1—C11—C16	125.90 (11)	C14—C21—C26—C25	177.63 (11)
C4—O2—C12—C13	−16.63 (16)	C15—C16—C31—C36	136.15 (11)
C4—O2—C12—C11	166.88 (10)	C11—C16—C31—C36	−43.63 (15)
C16—C11—C12—O2	179.15 (9)	C15—C16—C31—C32	−42.56 (15)
C1—C11—C12—O2	2.78 (14)	C11—C16—C31—C32	137.65 (11)
C16—C11—C12—C13	2.56 (16)	C36—C31—C32—C33	1.30 (17)
C1—C11—C12—C13	−173.81 (10)	C16—C31—C32—C33	−179.93 (10)
O2—C12—C13—C14	−177.79 (10)	C31—C32—C33—C34	−0.23 (17)
C11—C12—C13—C14	−1.52 (16)	C32—C33—C34—F2	179.12 (10)
C12—C13—C14—C15	−1.23 (16)	C32—C33—C34—C35	−0.65 (17)
C12—C13—C14—C21	175.78 (10)	F2—C34—C35—C36	−179.38 (10)
C13—C14—C15—C16	2.99 (16)	C33—C34—C35—C36	0.40 (18)
C21—C14—C15—C16	−174.03 (10)	C34—C35—C36—C31	0.74 (17)
C14—C15—C16—C11	−1.93 (16)	C32—C31—C36—C35	−1.56 (16)
C14—C15—C16—C31	178.28 (10)	C16—C31—C36—C35	179.71 (11)
C12—C11—C16—C15	−0.84 (15)	C2—C3—C41—C46	2.43 (19)
C1—C11—C16—C15	175.33 (10)	C2—C3—C41—C42	−176.82 (12)
C12—C11—C16—C31	178.95 (10)	C46—C41—C42—C43	−1.74 (18)
C1—C11—C16—C31	−4.88 (16)	C3—C41—C42—C43	177.54 (11)
C13—C14—C21—C26	134.17 (12)	C41—C42—C43—C44	−0.12 (19)
C15—C14—C21—C26	−48.86 (16)	C42—C43—C44—C45	1.5 (2)
C13—C14—C21—C22	−48.15 (15)	C43—C44—C45—C46	−1.0 (2)
C15—C14—C21—C22	128.83 (12)	C44—C45—C46—C41	−0.9 (2)
C26—C21—C22—C23	1.17 (17)	C42—C41—C46—C45	2.25 (18)
C14—C21—C22—C23	−176.58 (11)	C3—C41—C46—C45	−177.01 (11)
C21—C22—C23—C24	−1.12 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C25—H25···O1i	0.95	2.41	3.3092 (15)	157
C44—H44···F2ii	0.95	2.55	3.2761 (15)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C25—H25⋯O1i	0.95	2.41	3.3092 (15)	157
C44—H44⋯F2ii	0.95	2.55	3.2761 (15)	133

Symmetry codes: (i) ; (ii) .