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

The title compound, C(28)H(19)ClF(2)O(2), is a polysubstituted terphenyl derivative bearing a Michael system in which the C=C double bond has an E conformation. In the crystal, C-H⋯Cl and C-H⋯O contacts connect the mol-ecules into layers lying perpendicular to the a axis. The shortest inter-centroid distance between symmetry-related 4-fluoro-phenyl groups is 3.7547 (16) Å.

Related literature

For pharmacological background information about terphen­yls, see: Astrue (2002 ▶); Liu (2006 ▶). For the crystal structures of other terphenyl derivatives, see: Betz et al. (2011a ▶,b ▶,c ▶,d ▶,e ▶); Samshuddin et al. (2011 ▶). For graph-set analysis, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C28H19ClF2O2

M = 460.88

Monoclinic,

a = 14.2065 (7) Å

b = 6.8651 (3) Å

c = 22.4817 (11) Å

β = 101.406 (2)°

V = 2149.32 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 200 K

0.40 × 0.20 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.918, T max = 0.962

17828 measured reflections

5318 independent reflections

3817 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.141

S = 1.07

5318 reflections

299 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.31 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/S1600536812017692/su2410sup1.cif

Supplementary material file. DOI: 10.1107/S1600536812017692/su2410Isup2.cdx

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812017692/su2410Isup3.hkl

Supplementary material file. DOI: 10.1107/S1600536812017692/su2410Isup4.cml

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

C28H19ClF2O2	F(000) = 952
Mr = 460.88	Dx = 1.424 Mg m−3
Monoclinic, P21/c	Melting point: 452 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 14.2065 (7) Å	Cell parameters from 7266 reflections
b = 6.8651 (3) Å	θ = 2.6–28.2°
c = 22.4817 (11) Å	µ = 0.22 mm−1
β = 101.406 (2)°	T = 200 K
V = 2149.32 (18) Å3	Block, yellow
Z = 4	0.40 × 0.20 × 0.18 mm

Bruker APEXII CCD diffractometer	5318 independent reflections
Radiation source: fine-focus sealed tube	3817 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.051
φ and ω scans	θmax = 28.4°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −18→18
Tmin = 0.918, Tmax = 0.962	k = −9→8
17828 measured reflections	l = −29→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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0356P)2 + 2.7063P] where P = (Fo2 + 2Fc2)/3
5318 reflections	(Δ/σ)max < 0.001
299 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.31 e Å−3

	x	y	z	Uiso*/Ueq
Cl1	0.32945 (5)	0.46688 (11)	0.32261 (3)	0.0424 (2)
F1	0.48872 (13)	−0.3590 (3)	0.05070 (8)	0.0542 (5)
F2	−0.02840 (13)	0.4610 (3)	−0.34871 (6)	0.0483 (4)
O1	0.21690 (15)	0.2023 (3)	0.11598 (8)	0.0394 (5)
O2	0.10962 (14)	0.6409 (3)	0.04792 (7)	0.0360 (4)
C1	0.29266 (17)	0.5306 (4)	0.18625 (10)	0.0286 (5)
H1	0.2750	0.4189	0.2065	0.034*
C2	0.27497 (18)	0.5259 (4)	0.12635 (10)	0.0308 (5)
H2	0.2916	0.6354	0.1048	0.037*
C3	0.22992 (17)	0.3548 (4)	0.09182 (10)	0.0266 (5)
C4	0.0579 (2)	0.8171 (4)	0.03123 (12)	0.0380 (6)
H4A	0.0929	0.8975	0.0068	0.057*
H4B	0.0512	0.8885	0.0679	0.057*
H4C	−0.0059	0.7863	0.0075	0.057*
C11	0.33711 (17)	0.6927 (4)	0.22443 (10)	0.0280 (5)
C12	0.35889 (17)	0.6785 (4)	0.28769 (10)	0.0283 (5)
C13	0.40353 (19)	0.8263 (4)	0.32436 (12)	0.0353 (6)
H13	0.4168	0.8114	0.3672	0.042*
C14	0.4286 (2)	0.9946 (4)	0.29868 (13)	0.0410 (7)
H14	0.4612	1.0954	0.3235	0.049*
C15	0.4060 (2)	1.0165 (4)	0.23610 (14)	0.0440 (7)
H15	0.4217	1.1341	0.2180	0.053*
C16	0.3608 (2)	0.8686 (4)	0.20019 (12)	0.0378 (6)
H16	0.3453	0.8869	0.1575	0.045*
C21	0.19968 (16)	0.3801 (4)	0.02426 (10)	0.0250 (5)
C22	0.22967 (16)	0.2553 (3)	−0.01771 (10)	0.0236 (5)
C23	0.19342 (17)	0.2854 (4)	−0.07951 (10)	0.0262 (5)
H23	0.2142	0.2030	−0.1083	0.031*
C24	0.12777 (16)	0.4327 (4)	−0.09994 (10)	0.0250 (5)
C25	0.09855 (17)	0.5559 (4)	−0.05830 (10)	0.0271 (5)
H25	0.0537	0.6570	−0.0716	0.033*
C26	0.13545 (17)	0.5300 (4)	0.00332 (10)	0.0261 (5)
C31	0.29922 (17)	0.0940 (3)	0.00053 (10)	0.0245 (5)
C32	0.38279 (17)	0.1197 (4)	0.04463 (11)	0.0301 (5)
H32	0.3961	0.2434	0.0634	0.036*
C33	0.44637 (19)	−0.0325 (4)	0.06131 (11)	0.0359 (6)
H33	0.5026	−0.0150	0.0916	0.043*
C34	0.4265 (2)	−0.2090 (4)	0.03319 (12)	0.0360 (6)
C35	0.34726 (19)	−0.2412 (4)	−0.01133 (11)	0.0332 (6)
H35	0.3361	−0.3644	−0.0307	0.040*
C36	0.28382 (18)	−0.0874 (4)	−0.02719 (11)	0.0294 (5)
H36	0.2282	−0.1067	−0.0579	0.035*
C41	0.08695 (17)	0.4497 (4)	−0.16619 (10)	0.0263 (5)
C42	0.14603 (19)	0.4464 (4)	−0.20846 (11)	0.0314 (5)
H42	0.2137	0.4398	−0.1949	0.038*
C43	0.1081 (2)	0.4526 (4)	−0.27020 (11)	0.0350 (6)
H43	0.1487	0.4518	−0.2991	0.042*
C44	0.0103 (2)	0.4598 (4)	−0.28813 (10)	0.0335 (6)
C45	−0.05083 (19)	0.4642 (4)	−0.24832 (11)	0.0342 (6)
H45	−0.1184	0.4694	−0.2625	0.041*
C46	−0.01178 (18)	0.4607 (4)	−0.18650 (11)	0.0300 (5)
H46	−0.0529	0.4659	−0.1580	0.036*

	U11	U22	U33	U12	U13	U23
Cl1	0.0517 (4)	0.0472 (4)	0.0245 (3)	−0.0136 (3)	−0.0019 (3)	0.0057 (3)
F1	0.0605 (11)	0.0418 (10)	0.0580 (11)	0.0263 (9)	0.0060 (9)	0.0116 (8)
F2	0.0676 (12)	0.0481 (10)	0.0226 (7)	0.0027 (9)	−0.0072 (7)	0.0013 (7)
O1	0.0562 (12)	0.0328 (11)	0.0284 (9)	−0.0035 (10)	0.0062 (8)	0.0048 (8)
O2	0.0450 (11)	0.0365 (11)	0.0255 (8)	0.0141 (9)	0.0047 (7)	−0.0039 (8)
C1	0.0295 (12)	0.0278 (13)	0.0275 (11)	0.0002 (11)	0.0030 (9)	0.0031 (10)
C2	0.0332 (13)	0.0316 (14)	0.0269 (11)	−0.0026 (12)	0.0039 (10)	0.0013 (10)
C3	0.0270 (12)	0.0284 (13)	0.0246 (11)	0.0035 (11)	0.0055 (9)	0.0019 (10)
C4	0.0452 (16)	0.0288 (15)	0.0402 (14)	0.0087 (13)	0.0093 (12)	−0.0050 (11)
C11	0.0282 (12)	0.0287 (13)	0.0264 (11)	0.0008 (11)	0.0032 (9)	−0.0009 (10)
C12	0.0254 (12)	0.0296 (14)	0.0286 (12)	0.0000 (10)	0.0021 (9)	−0.0003 (10)
C13	0.0330 (13)	0.0405 (16)	0.0299 (12)	0.0000 (12)	0.0003 (10)	−0.0079 (11)
C14	0.0370 (15)	0.0354 (16)	0.0486 (16)	−0.0036 (13)	0.0032 (12)	−0.0113 (13)
C15	0.0499 (17)	0.0293 (15)	0.0536 (17)	−0.0066 (13)	0.0118 (14)	0.0007 (13)
C16	0.0485 (16)	0.0338 (15)	0.0301 (13)	−0.0005 (13)	0.0053 (11)	0.0015 (11)
C21	0.0257 (11)	0.0252 (12)	0.0227 (10)	−0.0021 (10)	0.0013 (9)	−0.0006 (9)
C22	0.0231 (11)	0.0219 (12)	0.0246 (11)	−0.0024 (10)	0.0014 (9)	0.0005 (9)
C23	0.0262 (12)	0.0264 (13)	0.0249 (11)	0.0006 (10)	0.0027 (9)	−0.0037 (9)
C24	0.0241 (11)	0.0260 (13)	0.0233 (10)	−0.0019 (10)	0.0006 (8)	0.0001 (9)
C25	0.0270 (12)	0.0246 (13)	0.0282 (11)	0.0028 (10)	0.0014 (9)	0.0001 (10)
C26	0.0296 (12)	0.0220 (12)	0.0265 (11)	−0.0005 (10)	0.0049 (9)	−0.0021 (9)
C31	0.0278 (12)	0.0224 (12)	0.0236 (10)	0.0012 (10)	0.0062 (9)	0.0022 (9)
C32	0.0298 (13)	0.0310 (14)	0.0285 (12)	0.0004 (11)	0.0030 (10)	−0.0015 (10)
C33	0.0308 (13)	0.0434 (17)	0.0313 (12)	0.0075 (13)	0.0007 (10)	0.0044 (12)
C34	0.0398 (15)	0.0346 (15)	0.0352 (13)	0.0129 (12)	0.0111 (11)	0.0121 (11)
C35	0.0427 (15)	0.0230 (13)	0.0360 (13)	0.0007 (12)	0.0130 (11)	0.0019 (11)
C36	0.0324 (13)	0.0268 (13)	0.0287 (12)	−0.0006 (11)	0.0052 (10)	0.0007 (10)
C41	0.0309 (12)	0.0226 (12)	0.0231 (10)	0.0011 (10)	−0.0006 (9)	−0.0016 (9)
C42	0.0315 (13)	0.0312 (14)	0.0302 (12)	0.0001 (11)	0.0026 (10)	−0.0007 (11)
C43	0.0454 (16)	0.0324 (15)	0.0277 (12)	−0.0013 (13)	0.0085 (11)	−0.0002 (11)
C44	0.0496 (16)	0.0262 (13)	0.0206 (11)	0.0017 (12)	−0.0034 (10)	0.0007 (10)
C45	0.0342 (13)	0.0310 (14)	0.0321 (12)	0.0026 (12)	−0.0063 (10)	0.0001 (11)
C46	0.0304 (13)	0.0306 (14)	0.0278 (11)	0.0020 (11)	0.0026 (9)	0.0006 (10)

Cl1—C12	1.741 (3)	C22—C31	1.487 (3)
F1—C34	1.364 (3)	C23—C24	1.391 (3)
F2—C44	1.364 (3)	C23—H23	0.9500
O1—C3	1.211 (3)	C24—C25	1.385 (3)
O2—C26	1.366 (3)	C24—C41	1.492 (3)
O2—C4	1.426 (3)	C25—C26	1.392 (3)
C1—C2	1.321 (3)	C25—H25	0.9500
C1—C11	1.470 (3)	C31—C36	1.390 (3)
C1—H1	0.9500	C31—C32	1.399 (3)
C2—C3	1.481 (3)	C32—C33	1.384 (4)
C2—H2	0.9500	C32—H32	0.9500
C3—C21	1.504 (3)	C33—C34	1.370 (4)
C4—H4A	0.9800	C33—H33	0.9500
C4—H4B	0.9800	C34—C35	1.368 (4)
C4—H4C	0.9800	C35—C36	1.388 (4)
C11—C16	1.393 (4)	C35—H35	0.9500
C11—C12	1.398 (3)	C36—H36	0.9500
C12—C13	1.380 (3)	C41—C42	1.387 (3)
C13—C14	1.369 (4)	C41—C46	1.389 (3)
C13—H13	0.9500	C42—C43	1.387 (3)
C14—C15	1.388 (4)	C42—H42	0.9500
C14—H14	0.9500	C43—C44	1.368 (4)
C15—C16	1.375 (4)	C43—H43	0.9500
C15—H15	0.9500	C44—C45	1.365 (4)
C16—H16	0.9500	C45—C46	1.391 (3)
C21—C26	1.394 (3)	C45—H45	0.9500
C21—C22	1.402 (3)	C46—H46	0.9500
C22—C23	1.398 (3)
C26—O2—C4	118.60 (19)	C25—C24—C41	121.2 (2)
C2—C1—C11	126.0 (2)	C23—C24—C41	119.3 (2)
C2—C1—H1	117.0	C24—C25—C26	119.4 (2)
C11—C1—H1	117.0	C24—C25—H25	120.3
C1—C2—C3	121.9 (2)	C26—C25—H25	120.3
C1—C2—H2	119.0	O2—C26—C25	123.8 (2)
C3—C2—H2	119.0	O2—C26—C21	114.6 (2)
O1—C3—C2	122.6 (2)	C25—C26—C21	121.5 (2)
O1—C3—C21	120.9 (2)	C36—C31—C32	117.8 (2)
C2—C3—C21	116.4 (2)	C36—C31—C22	120.4 (2)
O2—C4—H4A	109.5	C32—C31—C22	121.7 (2)
O2—C4—H4B	109.5	C33—C32—C31	120.9 (2)
H4A—C4—H4B	109.5	C33—C32—H32	119.5
O2—C4—H4C	109.5	C31—C32—H32	119.5
H4A—C4—H4C	109.5	C34—C33—C32	118.6 (2)
H4B—C4—H4C	109.5	C34—C33—H33	120.7
C16—C11—C12	115.9 (2)	C32—C33—H33	120.7
C16—C11—C1	122.5 (2)	F1—C34—C35	118.8 (3)
C12—C11—C1	121.6 (2)	F1—C34—C33	118.1 (2)
C13—C12—C11	122.6 (2)	C35—C34—C33	123.1 (2)
C13—C12—Cl1	117.85 (19)	C34—C35—C36	117.6 (2)
C11—C12—Cl1	119.51 (19)	C34—C35—H35	121.2
C14—C13—C12	119.7 (2)	C36—C35—H35	121.2
C14—C13—H13	120.1	C35—C36—C31	122.0 (2)
C12—C13—H13	120.1	C35—C36—H36	119.0
C13—C14—C15	119.4 (3)	C31—C36—H36	119.0
C13—C14—H14	120.3	C42—C41—C46	119.0 (2)
C15—C14—H14	120.3	C42—C41—C24	120.9 (2)
C16—C15—C14	120.2 (3)	C46—C41—C24	120.0 (2)
C16—C15—H15	119.9	C43—C42—C41	121.1 (2)
C14—C15—H15	119.9	C43—C42—H42	119.4
C15—C16—C11	122.1 (2)	C41—C42—H42	119.4
C15—C16—H16	119.0	C44—C43—C42	117.8 (2)
C11—C16—H16	119.0	C44—C43—H43	121.1
C26—C21—C22	119.3 (2)	C42—C43—H43	121.1
C26—C21—C3	117.6 (2)	F2—C44—C45	118.1 (2)
C22—C21—C3	123.0 (2)	F2—C44—C43	118.7 (2)
C23—C22—C21	118.5 (2)	C45—C44—C43	123.2 (2)
C23—C22—C31	118.6 (2)	C44—C45—C46	118.4 (2)
C21—C22—C31	122.9 (2)	C44—C45—H45	120.8
C24—C23—C22	121.8 (2)	C46—C45—H45	120.8
C24—C23—H23	119.1	C41—C46—C45	120.5 (2)
C22—C23—H23	119.1	C41—C46—H46	119.8
C25—C24—C23	119.5 (2)	C45—C46—H46	119.8
C11—C1—C2—C3	179.9 (2)	C24—C25—C26—C21	−1.5 (4)
C1—C2—C3—O1	−8.7 (4)	C22—C21—C26—O2	178.9 (2)
C1—C2—C3—C21	170.7 (2)	C3—C21—C26—O2	1.8 (3)
C2—C1—C11—C16	4.0 (4)	C22—C21—C26—C25	1.6 (4)
C2—C1—C11—C12	−175.5 (3)	C3—C21—C26—C25	−175.6 (2)
C16—C11—C12—C13	−1.7 (4)	C23—C22—C31—C36	−43.5 (3)
C1—C11—C12—C13	177.8 (2)	C21—C22—C31—C36	137.3 (2)
C16—C11—C12—Cl1	178.4 (2)	C23—C22—C31—C32	135.0 (2)
C1—C11—C12—Cl1	−2.0 (3)	C21—C22—C31—C32	−44.2 (3)
C11—C12—C13—C14	−0.4 (4)	C36—C31—C32—C33	−1.9 (4)
Cl1—C12—C13—C14	179.5 (2)	C22—C31—C32—C33	179.6 (2)
C12—C13—C14—C15	2.0 (4)	C31—C32—C33—C34	0.8 (4)
C13—C14—C15—C16	−1.6 (4)	C32—C33—C34—F1	−178.9 (2)
C14—C15—C16—C11	−0.7 (5)	C32—C33—C34—C35	1.0 (4)
C12—C11—C16—C15	2.3 (4)	F1—C34—C35—C36	178.4 (2)
C1—C11—C16—C15	−177.3 (3)	C33—C34—C35—C36	−1.5 (4)
O1—C3—C21—C26	122.1 (3)	C34—C35—C36—C31	0.2 (4)
C2—C3—C21—C26	−57.3 (3)	C32—C31—C36—C35	1.4 (4)
O1—C3—C21—C22	−54.9 (3)	C22—C31—C36—C35	180.0 (2)
C2—C3—C21—C22	125.6 (3)	C25—C24—C41—C42	134.0 (3)
C26—C21—C22—C23	−0.3 (3)	C23—C24—C41—C42	−48.6 (3)
C3—C21—C22—C23	176.7 (2)	C25—C24—C41—C46	−48.7 (3)
C26—C21—C22—C31	178.9 (2)	C23—C24—C41—C46	128.6 (3)
C3—C21—C22—C31	−4.1 (4)	C46—C41—C42—C43	−0.4 (4)
C21—C22—C23—C24	−1.1 (4)	C24—C41—C42—C43	176.8 (2)
C31—C22—C23—C24	179.7 (2)	C41—C42—C43—C44	−0.7 (4)
C22—C23—C24—C25	1.3 (4)	C42—C43—C44—F2	−178.4 (2)
C22—C23—C24—C41	−176.1 (2)	C42—C43—C44—C45	1.0 (4)
C23—C24—C25—C26	0.0 (4)	F2—C44—C45—C46	179.3 (2)
C41—C24—C25—C26	177.4 (2)	C43—C44—C45—C46	−0.1 (4)
C4—O2—C26—C25	−13.5 (4)	C42—C41—C46—C45	1.4 (4)
C4—O2—C26—C21	169.2 (2)	C24—C41—C46—C45	−175.9 (2)
C24—C25—C26—O2	−178.5 (2)	C44—C45—C46—C41	−1.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C23—H23···Cl1i	0.95	2.73	3.641 (2)	161
C33—H33···Cl1ii	0.95	2.76	3.697 (3)	170
C43—H43···O1i	0.95	2.54	3.411 (3)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C23—H23⋯Cl1i	0.95	2.73	3.641 (2)	161
C33—H33⋯Cl1ii	0.95	2.76	3.697 (3)	170
C43—H43⋯O1i	0.95	2.54	3.411 (3)	153

Symmetry codes: (i) ; (ii) .