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

In the title compound, C(28)H(19)F(2)NO(4), a polysubstituted terphenyl derivative bearing a Michael system, the C=C double bond has an E configuration. Two C-H⋯F contacts connect mol-ecules into inversion dimers. In addition, a C-H⋯π as well as a C-F⋯π contact can be identified. The shortest centroid-centroid distance between two aromatic rings is 3.9535 (8) Å, between one of the para-fluoro-benzene rings 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 chalcone derivatives, 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

C28H19F2NO4

M = 471.44

Monoclinic,

a = 23.3751 (7) Å

b = 6.9098 (2) Å

c = 13.7879 (5) Å

β = 99.243 (2)°

V = 2198.07 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 200 K

0.58 × 0.44 × 0.17 mm

Data collection

Bruker APEXII CCD diffractometer

37111 measured reflections

5462 independent reflections

4899 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.114

S = 1.05

5462 reflections

317 parameters

H-atom parameters constrained

Δρmax = 0.32 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/S1600536811045806/fj2465sup1.cif

Supplementary material file. DOI: 10.1107/S1600536811045806/fj2465Isup2.cdx

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811045806/fj2465Isup3.hkl

Supplementary material file. DOI: 10.1107/S1600536811045806/fj2465Isup4.cml

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

C28H19F2NO4	F(000) = 976
Mr = 471.44	Dx = 1.425 Mg m−3
Monoclinic, P21/c	Melting point: 489 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 23.3751 (7) Å	Cell parameters from 9792 reflections
b = 6.9098 (2) Å	θ = 2.7–28.4°
c = 13.7879 (5) Å	µ = 0.11 mm−1
β = 99.243 (2)°	T = 200 K
V = 2198.07 (12) Å3	Block, yellow
Z = 4	0.58 × 0.44 × 0.17 mm

Bruker APEXII CCD diffractometer	4899 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.026
graphite	θmax = 28.4°, θmin = 1.8°
φ and ω scans	h = −31→31
37111 measured reflections	k = −9→9
5462 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0442P)2 + 1.0552P] where P = (Fo2 + 2Fc2)/3
5462 reflections	(Δ/σ)max < 0.001
317 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

	x	y	z	Uiso*/Ueq
F1	0.54918 (4)	0.89243 (16)	0.09405 (8)	0.0577 (3)
F2	0.14304 (5)	0.02099 (15)	0.26896 (8)	0.0585 (3)
O1	0.25621 (5)	0.57681 (15)	0.56774 (8)	0.0428 (2)
O2	0.32555 (5)	1.02608 (15)	0.54905 (8)	0.0426 (2)
O3	−0.01724 (6)	1.5042 (2)	0.61968 (11)	0.0651 (4)
O4	−0.06990 (5)	1.2537 (2)	0.63545 (13)	0.0765 (5)
N1	−0.02455 (6)	1.3295 (2)	0.62244 (10)	0.0480 (3)
C1	0.25169 (5)	0.72612 (19)	0.52066 (9)	0.0310 (3)
C2	0.20726 (6)	0.8734 (2)	0.53077 (10)	0.0346 (3)
H2	0.2095	0.9969	0.5013	0.042*
C3	0.16442 (6)	0.8363 (2)	0.58026 (10)	0.0348 (3)
H3	0.1650	0.7142	0.6121	0.042*
C4	0.35123 (8)	1.2132 (2)	0.55848 (11)	0.0460 (3)
H4A	0.3935	1.2006	0.5682	0.069*
H4B	0.3397	1.2798	0.6151	0.069*
H4C	0.3382	1.2882	0.4987	0.069*
C11	0.29155 (5)	0.76687 (18)	0.44743 (9)	0.0291 (2)
C12	0.33024 (6)	0.92135 (18)	0.46656 (9)	0.0314 (3)
C13	0.37199 (5)	0.95644 (19)	0.40751 (9)	0.0314 (3)
H13	0.3990	1.0591	0.4228	0.038*
C14	0.37401 (5)	0.83985 (18)	0.32563 (9)	0.0287 (2)
C15	0.33356 (5)	0.69187 (18)	0.30343 (9)	0.0284 (2)
H15	0.3338	0.6170	0.2457	0.034*
C16	0.29257 (5)	0.65097 (17)	0.36424 (9)	0.0274 (2)
C21	0.41994 (5)	0.86685 (17)	0.26396 (9)	0.0292 (2)
C22	0.47750 (6)	0.89612 (19)	0.30685 (10)	0.0338 (3)
H22	0.4870	0.9087	0.3762	0.041*
C23	0.52104 (6)	0.9071 (2)	0.24956 (11)	0.0386 (3)
H23	0.5602	0.9277	0.2787	0.046*
C24	0.50613 (6)	0.8877 (2)	0.14999 (11)	0.0394 (3)
C25	0.45022 (7)	0.8625 (2)	0.10411 (11)	0.0410 (3)
H25	0.4413	0.8524	0.0346	0.049*
C26	0.40697 (6)	0.8522 (2)	0.16222 (10)	0.0356 (3)
H26	0.3678	0.8348	0.1319	0.043*
C31	0.25194 (5)	0.48643 (18)	0.33831 (9)	0.0278 (2)
C32	0.27220 (6)	0.31378 (19)	0.30383 (10)	0.0331 (3)
H32	0.3119	0.3038	0.2968	0.040*
C33	0.23598 (6)	0.1566 (2)	0.27957 (10)	0.0384 (3)
H33	0.2501	0.0399	0.2556	0.046*
C34	0.17884 (6)	0.1751 (2)	0.29133 (11)	0.0390 (3)
C35	0.15653 (6)	0.3426 (2)	0.32347 (10)	0.0381 (3)
H35	0.1168	0.3510	0.3300	0.046*
C36	0.19314 (5)	0.4991 (2)	0.34611 (10)	0.0329 (3)
H36	0.1781	0.6168	0.3672	0.039*
C41	0.11626 (6)	0.9660 (2)	0.59044 (9)	0.0334 (3)
C42	0.11732 (6)	1.1622 (2)	0.56648 (11)	0.0388 (3)
H42	0.1500	1.2140	0.5423	0.047*
C43	0.07152 (6)	1.2819 (2)	0.57750 (11)	0.0407 (3)
H43	0.0725	1.4158	0.5623	0.049*
C44	0.02418 (6)	1.2015 (2)	0.61122 (10)	0.0378 (3)
C45	0.02118 (6)	1.0089 (2)	0.63473 (11)	0.0414 (3)
H45	−0.0122	0.9574	0.6568	0.050*
C46	0.06796 (6)	0.8922 (2)	0.62547 (11)	0.0395 (3)
H46	0.0672	0.7595	0.6433	0.047*

	U11	U22	U33	U12	U13	U23
F1	0.0536 (6)	0.0593 (6)	0.0704 (6)	0.0013 (5)	0.0407 (5)	0.0106 (5)
F2	0.0576 (6)	0.0439 (5)	0.0721 (7)	−0.0193 (4)	0.0047 (5)	−0.0043 (5)
O1	0.0448 (5)	0.0411 (5)	0.0462 (6)	0.0121 (4)	0.0186 (4)	0.0126 (4)
O2	0.0513 (6)	0.0372 (5)	0.0438 (5)	−0.0048 (4)	0.0208 (5)	−0.0128 (4)
O3	0.0632 (8)	0.0562 (8)	0.0811 (9)	0.0269 (6)	0.0276 (7)	0.0082 (7)
O4	0.0345 (6)	0.0864 (11)	0.1117 (12)	0.0079 (6)	0.0207 (7)	−0.0264 (9)
N1	0.0370 (6)	0.0639 (9)	0.0438 (7)	0.0154 (6)	0.0084 (5)	−0.0087 (6)
C1	0.0300 (6)	0.0330 (6)	0.0312 (6)	0.0043 (5)	0.0084 (5)	−0.0003 (5)
C2	0.0362 (6)	0.0341 (6)	0.0355 (6)	0.0077 (5)	0.0118 (5)	0.0020 (5)
C3	0.0340 (6)	0.0346 (7)	0.0373 (6)	0.0057 (5)	0.0102 (5)	0.0005 (5)
C4	0.0619 (9)	0.0356 (7)	0.0392 (7)	0.0010 (7)	0.0041 (7)	−0.0078 (6)
C11	0.0281 (5)	0.0288 (6)	0.0316 (6)	0.0060 (5)	0.0085 (4)	0.0021 (5)
C12	0.0337 (6)	0.0283 (6)	0.0331 (6)	0.0051 (5)	0.0082 (5)	−0.0022 (5)
C13	0.0303 (6)	0.0278 (6)	0.0368 (6)	0.0015 (5)	0.0071 (5)	−0.0007 (5)
C14	0.0266 (5)	0.0281 (6)	0.0322 (6)	0.0056 (4)	0.0076 (4)	0.0032 (5)
C15	0.0287 (5)	0.0277 (6)	0.0300 (5)	0.0044 (4)	0.0076 (4)	−0.0005 (4)
C16	0.0259 (5)	0.0254 (5)	0.0313 (6)	0.0057 (4)	0.0063 (4)	0.0019 (4)
C21	0.0293 (6)	0.0244 (5)	0.0353 (6)	0.0026 (4)	0.0099 (5)	0.0021 (5)
C22	0.0324 (6)	0.0314 (6)	0.0383 (6)	−0.0004 (5)	0.0078 (5)	0.0018 (5)
C23	0.0304 (6)	0.0328 (7)	0.0544 (8)	−0.0012 (5)	0.0123 (6)	0.0049 (6)
C24	0.0419 (7)	0.0304 (6)	0.0522 (8)	0.0017 (5)	0.0264 (6)	0.0075 (6)
C25	0.0490 (8)	0.0402 (7)	0.0370 (7)	−0.0005 (6)	0.0166 (6)	0.0052 (6)
C26	0.0344 (6)	0.0365 (7)	0.0367 (7)	0.0003 (5)	0.0082 (5)	0.0047 (5)
C31	0.0278 (5)	0.0292 (6)	0.0270 (5)	0.0034 (4)	0.0061 (4)	0.0025 (4)
C32	0.0338 (6)	0.0314 (6)	0.0354 (6)	0.0047 (5)	0.0093 (5)	0.0008 (5)
C33	0.0464 (8)	0.0290 (6)	0.0400 (7)	0.0031 (5)	0.0074 (6)	−0.0016 (5)
C34	0.0422 (7)	0.0347 (7)	0.0389 (7)	−0.0082 (6)	0.0026 (5)	0.0026 (5)
C35	0.0297 (6)	0.0443 (8)	0.0402 (7)	−0.0026 (5)	0.0057 (5)	0.0018 (6)
C36	0.0287 (6)	0.0341 (6)	0.0364 (6)	0.0039 (5)	0.0071 (5)	−0.0005 (5)
C41	0.0314 (6)	0.0382 (7)	0.0322 (6)	0.0051 (5)	0.0100 (5)	−0.0004 (5)
C42	0.0365 (7)	0.0412 (7)	0.0420 (7)	0.0062 (6)	0.0164 (5)	0.0044 (6)
C43	0.0423 (7)	0.0414 (7)	0.0405 (7)	0.0105 (6)	0.0124 (6)	0.0039 (6)
C44	0.0307 (6)	0.0505 (8)	0.0324 (6)	0.0105 (6)	0.0055 (5)	−0.0059 (6)
C45	0.0319 (6)	0.0518 (9)	0.0433 (7)	−0.0012 (6)	0.0142 (5)	−0.0064 (6)
C46	0.0383 (7)	0.0389 (7)	0.0440 (7)	0.0006 (6)	0.0146 (6)	−0.0018 (6)

F1—C24	1.3630 (15)	C22—C23	1.3870 (18)
F2—C34	1.3586 (16)	C22—H22	0.9500
O1—C1	1.2145 (16)	C23—C24	1.368 (2)
O2—C12	1.3673 (15)	C23—H23	0.9500
O2—C4	1.4230 (18)	C24—C25	1.368 (2)
O3—N1	1.221 (2)	C25—C26	1.3889 (18)
O4—N1	1.2209 (19)	C25—H25	0.9500
N1—C44	1.4698 (18)	C26—H26	0.9500
C1—C2	1.4764 (17)	C31—C32	1.3949 (17)
C1—C11	1.5063 (16)	C31—C36	1.3985 (17)
C2—C3	1.3243 (18)	C32—C33	1.3848 (19)
C2—H2	0.9500	C32—H32	0.9500
C3—C41	1.4630 (17)	C33—C34	1.377 (2)
C3—H3	0.9500	C33—H33	0.9500
C4—H4A	0.9800	C34—C35	1.372 (2)
C4—H4B	0.9800	C35—C36	1.3832 (19)
C4—H4C	0.9800	C35—H35	0.9500
C11—C12	1.3965 (18)	C36—H36	0.9500
C11—C16	1.4022 (17)	C41—C46	1.3939 (19)
C12—C13	1.3890 (17)	C41—C42	1.397 (2)
C13—C14	1.3939 (17)	C42—C43	1.3802 (19)
C13—H13	0.9500	C42—H42	0.9500
C14—C15	1.3930 (17)	C43—C44	1.384 (2)
C14—C21	1.4844 (16)	C43—H43	0.9500
C15—C16	1.3997 (16)	C44—C45	1.374 (2)
C15—H15	0.9500	C45—C46	1.381 (2)
C16—C31	1.4877 (17)	C45—H45	0.9500
C21—C26	1.3905 (18)	C46—H46	0.9500
C21—C22	1.3948 (18)
C12—O2—C4	117.90 (11)	F1—C24—C23	118.25 (14)
O4—N1—O3	123.89 (14)	F1—C24—C25	118.59 (14)
O4—N1—C44	117.61 (15)	C23—C24—C25	123.16 (12)
O3—N1—C44	118.49 (14)	C24—C25—C26	118.00 (13)
O1—C1—C2	122.49 (12)	C24—C25—H25	121.0
O1—C1—C11	120.47 (11)	C26—C25—H25	121.0
C2—C1—C11	117.04 (11)	C25—C26—C21	121.16 (13)
C3—C2—C1	121.13 (13)	C25—C26—H26	119.4
C3—C2—H2	119.4	C21—C26—H26	119.4
C1—C2—H2	119.4	C32—C31—C36	118.13 (12)
C2—C3—C41	126.04 (13)	C32—C31—C16	119.80 (11)
C2—C3—H3	117.0	C36—C31—C16	122.07 (11)
C41—C3—H3	117.0	C33—C32—C31	121.69 (12)
O2—C4—H4A	109.5	C33—C32—H32	119.2
O2—C4—H4B	109.5	C31—C32—H32	119.2
H4A—C4—H4B	109.5	C34—C33—C32	117.75 (13)
O2—C4—H4C	109.5	C34—C33—H33	121.1
H4A—C4—H4C	109.5	C32—C33—H33	121.1
H4B—C4—H4C	109.5	F2—C34—C35	118.84 (13)
C12—C11—C16	119.70 (11)	F2—C34—C33	118.30 (13)
C12—C11—C1	117.89 (11)	C35—C34—C33	122.85 (13)
C16—C11—C1	122.35 (11)	C34—C35—C36	118.63 (12)
O2—C12—C13	123.57 (12)	C34—C35—H35	120.7
O2—C12—C11	115.19 (11)	C36—C35—H35	120.7
C13—C12—C11	121.16 (11)	C35—C36—C31	120.91 (12)
C12—C13—C14	119.49 (12)	C35—C36—H36	119.5
C12—C13—H13	120.3	C31—C36—H36	119.5
C14—C13—H13	120.3	C46—C41—C42	118.89 (12)
C15—C14—C13	119.48 (11)	C46—C41—C3	119.20 (13)
C15—C14—C21	119.62 (11)	C42—C41—C3	121.91 (12)
C13—C14—C21	120.87 (11)	C43—C42—C41	120.79 (13)
C14—C15—C16	121.49 (11)	C43—C42—H42	119.6
C14—C15—H15	119.3	C41—C42—H42	119.6
C16—C15—H15	119.3	C42—C43—C44	118.22 (14)
C15—C16—C11	118.55 (11)	C42—C43—H43	120.9
C15—C16—C31	118.84 (11)	C44—C43—H43	120.9
C11—C16—C31	122.61 (11)	C45—C44—C43	122.82 (13)
C26—C21—C22	118.52 (12)	C45—C44—N1	119.22 (13)
C26—C21—C14	120.55 (11)	C43—C44—N1	117.96 (14)
C22—C21—C14	120.83 (11)	C44—C45—C46	118.19 (13)
C23—C22—C21	120.84 (13)	C44—C45—H45	120.9
C23—C22—H22	119.6	C46—C45—H45	120.9
C21—C22—H22	119.6	C45—C46—C41	121.07 (14)
C24—C23—C22	118.31 (13)	C45—C46—H46	119.5
C24—C23—H23	120.8	C41—C46—H46	119.5
C22—C23—H23	120.8
O1—C1—C2—C3	−10.8 (2)	C23—C24—C25—C26	−1.4 (2)
C11—C1—C2—C3	168.41 (13)	C24—C25—C26—C21	0.0 (2)
C1—C2—C3—C41	−176.23 (13)	C22—C21—C26—C25	1.2 (2)
O1—C1—C11—C12	−114.27 (15)	C14—C21—C26—C25	−175.06 (12)
C2—C1—C11—C12	66.55 (15)	C15—C16—C31—C32	41.00 (16)
O1—C1—C11—C16	62.98 (18)	C11—C16—C31—C32	−138.88 (12)
C2—C1—C11—C16	−116.20 (13)	C15—C16—C31—C36	−138.17 (12)
C4—O2—C12—C13	20.49 (19)	C11—C16—C31—C36	41.95 (17)
C4—O2—C12—C11	−162.74 (12)	C36—C31—C32—C33	−1.30 (19)
C16—C11—C12—O2	179.64 (11)	C16—C31—C32—C33	179.50 (12)
C1—C11—C12—O2	−3.03 (17)	C31—C32—C33—C34	−0.5 (2)
C16—C11—C12—C13	−3.51 (18)	C32—C33—C34—F2	−179.18 (12)
C1—C11—C12—C13	173.82 (11)	C32—C33—C34—C35	1.6 (2)
O2—C12—C13—C14	178.94 (12)	F2—C34—C35—C36	−179.97 (12)
C11—C12—C13—C14	2.35 (19)	C33—C34—C35—C36	−0.7 (2)
C12—C13—C14—C15	1.00 (18)	C34—C35—C36—C31	−1.2 (2)
C12—C13—C14—C21	−176.80 (11)	C32—C31—C36—C35	2.18 (19)
C13—C14—C15—C16	−3.23 (18)	C16—C31—C36—C35	−178.64 (12)
C21—C14—C15—C16	174.59 (11)	C2—C3—C41—C46	165.67 (14)
C14—C15—C16—C11	2.07 (17)	C2—C3—C41—C42	−14.6 (2)
C14—C15—C16—C31	−177.81 (11)	C46—C41—C42—C43	0.2 (2)
C12—C11—C16—C15	1.28 (17)	C3—C41—C42—C43	−179.47 (13)
C1—C11—C16—C15	−175.93 (11)	C41—C42—C43—C44	−1.1 (2)
C12—C11—C16—C31	−178.84 (11)	C42—C43—C44—C45	0.5 (2)
C1—C11—C16—C31	3.96 (18)	C42—C43—C44—N1	−179.77 (13)
C15—C14—C21—C26	41.97 (17)	O4—N1—C44—C45	−12.8 (2)
C13—C14—C21—C26	−140.23 (13)	O3—N1—C44—C45	166.21 (15)
C15—C14—C21—C22	−134.25 (13)	O4—N1—C44—C43	167.52 (15)
C13—C14—C21—C22	43.55 (17)	O3—N1—C44—C43	−13.5 (2)
C26—C21—C22—C23	−1.07 (19)	C43—C44—C45—C46	1.0 (2)
C14—C21—C22—C23	175.23 (12)	N1—C44—C45—C46	−178.73 (13)
C21—C22—C23—C24	−0.3 (2)	C44—C45—C46—C41	−1.9 (2)
C22—C23—C24—F1	−177.96 (12)	C42—C41—C46—C45	1.3 (2)
C22—C23—C24—C25	1.6 (2)	C3—C41—C46—C45	−178.97 (13)
F1—C24—C25—C26	178.13 (13)

Cg1 is the centroid of the C11–C16 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C25—H25···F1i	0.95	2.54	3.2165 (17)	129
C33—H33···Cg1ii	0.95	2.91	3.4748 (15)	119
C24—F1···Cg1iii	1.3630 (15)	3.9512 (12)	4.8373 (15)	123.40 (8)

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C11–C16 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C25—H25⋯F1i	0.95	2.54	3.2165 (17)	129
C33—H33⋯Cg1ii	0.95	2.91	3.4748 (15)	119
C24—F1⋯Cg1iii	1.36 (1)	3.95 (1)	4.8373 (15)	123 (1)

Symmetry codes: (i) ; (ii) ; (iii) .