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

The title compound, C(29)H(22)F(2)O(3), is a meta-terphenyl derivative featuring a Michael-system-derived substituent with an E-configured C=C function. In the crystal, C-H⋯O and C-H⋯F contacts connect the mol-ecules into planes parallel to (101). The shortest centroid-centroid distance between two aromatic systems is 3.7169 (7) Å and is apparent between the terminal benzene ring of the Michael-system-derived substituent 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. (2011 ▶); Fun et al. (2010 ▶); Jasinski et al. (2010 ▶); Baktır et al. (2011 ▶). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C29H22F2O3

M = 456.47

Monoclinic,

a = 9.6059 (2) Å

b = 19.2236 (5) Å

c = 13.3772 (3) Å

β = 112.905 (1)°

V = 2275.46 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 200 K

0.54 × 0.51 × 0.51 mm

Data collection

Bruker APEXII CCD diffractometer

20209 measured reflections

5655 independent reflections

4754 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.125

S = 1.03

5655 reflections

309 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.28 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/S1600536811047696/qk2026sup1.cif

Supplementary material file. DOI: 10.1107/S1600536811047696/qk2026Isup2.cdx

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811047696/qk2026Isup3.hkl

Supplementary material file. DOI: 10.1107/S1600536811047696/qk2026Isup4.cml

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

C29H22F2O3	F(000) = 952
Mr = 456.47	Dx = 1.332 Mg m−3
Monoclinic, P21/c	Melting point: 453 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 9.6059 (2) Å	Cell parameters from 9984 reflections
b = 19.2236 (5) Å	θ = 2.3–28.3°
c = 13.3772 (3) Å	µ = 0.10 mm−1
β = 112.905 (1)°	T = 200 K
V = 2275.46 (9) Å3	Block, colourless
Z = 4	0.54 × 0.51 × 0.51 mm

Bruker APEXII CCD diffractometer	4754 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.032
graphite	θmax = 28.3°, θmin = 2.0°
φ and ω scans	h = −12→12
20209 measured reflections	k = −25→16
5655 independent reflections	l = −17→17

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) = 0.125	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0584P)2 + 0.9094P] where P = (Fo2 + 2Fc2)/3
5655 reflections	(Δ/σ)max < 0.001
309 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

	x	y	z	Uiso*/Ueq
F1	1.26002 (12)	0.02346 (5)	0.34310 (8)	0.0531 (3)
F2	1.29595 (14)	0.18370 (8)	1.21317 (8)	0.0771 (4)
O1	0.72100 (12)	0.25739 (5)	0.81288 (8)	0.0372 (2)
O2	0.56634 (10)	0.17164 (5)	0.56481 (7)	0.0331 (2)
O3	0.22589 (11)	−0.09964 (5)	0.91422 (8)	0.0364 (2)
C1	0.70335 (13)	0.19685 (6)	0.78248 (9)	0.0255 (2)
C2	0.59846 (14)	0.15198 (7)	0.80742 (10)	0.0295 (3)
H2	0.5335	0.1731	0.8369	0.035*
C3	0.58766 (13)	0.08347 (7)	0.79165 (10)	0.0271 (2)
H3	0.6480	0.0636	0.7572	0.033*
C4	0.48881 (15)	0.16369 (9)	0.45031 (11)	0.0394 (3)
H4A	0.4974	0.1154	0.4301	0.059*
H4B	0.5338	0.1947	0.4129	0.059*
H4C	0.3820	0.1756	0.4293	0.059*
C5	0.23701 (19)	−0.17318 (8)	0.90367 (14)	0.0429 (3)
H5A	0.3431	−0.1874	0.9382	0.064*
H5B	0.1975	−0.1857	0.8266	0.064*
H5C	0.1780	−0.1969	0.9390	0.064*
C11	0.79205 (13)	0.16861 (6)	0.71955 (9)	0.0236 (2)
C12	0.71812 (13)	0.15845 (6)	0.60728 (9)	0.0245 (2)
C13	0.79734 (13)	0.13784 (7)	0.54504 (9)	0.0262 (2)
H13	0.7452	0.1310	0.4692	0.031*
C14	0.95320 (13)	0.12709 (6)	0.59309 (9)	0.0257 (2)
C15	1.02729 (13)	0.13882 (7)	0.70402 (10)	0.0283 (3)
H15	1.1338	0.1330	0.7372	0.034*
C16	0.94848 (13)	0.15899 (6)	0.76765 (9)	0.0256 (2)
C21	1.03663 (13)	0.10142 (7)	0.52704 (10)	0.0265 (2)
C22	0.98189 (16)	0.11293 (9)	0.41562 (11)	0.0384 (3)
H22	0.8925	0.1396	0.3816	0.046*
C23	1.05596 (18)	0.08598 (9)	0.35336 (12)	0.0435 (4)
H23	1.0168	0.0929	0.2771	0.052*
C24	1.18607 (17)	0.04932 (8)	0.40404 (12)	0.0366 (3)
C25	1.24621 (17)	0.03782 (8)	0.51371 (12)	0.0404 (3)
H25	1.3383	0.0130	0.5472	0.048*
C26	1.16917 (15)	0.06331 (8)	0.57462 (11)	0.0353 (3)
H26	1.2078	0.0545	0.6505	0.042*
C31	1.03597 (13)	0.16740 (7)	0.88673 (9)	0.0290 (3)
C32	1.1509 (2)	0.21657 (9)	0.92460 (12)	0.0494 (4)
H32	1.1697	0.2463	0.8745	0.059*
C33	1.2391 (2)	0.22275 (11)	1.03526 (14)	0.0601 (5)
H33	1.3168	0.2567	1.0615	0.072*
C34	1.21002 (18)	0.17847 (11)	1.10472 (11)	0.0501 (4)
C35	1.10140 (19)	0.12816 (12)	1.07091 (12)	0.0538 (5)
H35	1.0867	0.0973	1.1214	0.065*
C36	1.01272 (16)	0.12334 (10)	0.96049 (11)	0.0442 (4)
H36	0.9351	0.0893	0.9354	0.053*
C41	0.49220 (13)	0.03587 (6)	0.82201 (9)	0.0261 (2)
C42	0.49079 (14)	−0.03467 (7)	0.79823 (10)	0.0298 (3)
H42	0.5519	−0.0509	0.7618	0.036*
C43	0.40287 (15)	−0.08220 (7)	0.82603 (10)	0.0310 (3)
H43	0.4035	−0.1301	0.8086	0.037*
C44	0.31392 (14)	−0.05848 (7)	0.87982 (10)	0.0282 (2)
C45	0.31186 (14)	0.01215 (7)	0.90335 (10)	0.0285 (3)
H45	0.2493	0.0283	0.9387	0.034*
C46	0.39985 (13)	0.05836 (7)	0.87571 (10)	0.0272 (2)
H46	0.3985	0.1062	0.8930	0.033*

	U11	U22	U33	U12	U13	U23
F1	0.0621 (6)	0.0616 (6)	0.0549 (6)	0.0049 (5)	0.0437 (5)	−0.0110 (5)
F2	0.0674 (7)	0.1271 (12)	0.0192 (4)	0.0025 (7)	−0.0025 (4)	−0.0068 (5)
O1	0.0469 (6)	0.0328 (5)	0.0397 (5)	−0.0057 (4)	0.0254 (4)	−0.0092 (4)
O2	0.0227 (4)	0.0522 (6)	0.0219 (4)	0.0035 (4)	0.0059 (3)	−0.0026 (4)
O3	0.0441 (5)	0.0325 (5)	0.0414 (5)	−0.0044 (4)	0.0263 (4)	−0.0002 (4)
C1	0.0262 (5)	0.0306 (6)	0.0199 (5)	0.0001 (4)	0.0093 (4)	−0.0011 (4)
C2	0.0301 (6)	0.0349 (7)	0.0283 (6)	0.0000 (5)	0.0168 (5)	−0.0023 (5)
C3	0.0258 (5)	0.0345 (6)	0.0229 (5)	0.0010 (5)	0.0115 (4)	−0.0011 (5)
C4	0.0257 (6)	0.0624 (9)	0.0237 (6)	0.0019 (6)	0.0027 (5)	−0.0031 (6)
C5	0.0580 (9)	0.0317 (7)	0.0477 (8)	−0.0039 (6)	0.0301 (7)	0.0011 (6)
C11	0.0260 (5)	0.0260 (5)	0.0197 (5)	−0.0005 (4)	0.0100 (4)	−0.0003 (4)
C12	0.0222 (5)	0.0294 (6)	0.0211 (5)	−0.0003 (4)	0.0074 (4)	0.0001 (4)
C13	0.0271 (5)	0.0329 (6)	0.0173 (5)	0.0003 (5)	0.0073 (4)	−0.0011 (4)
C14	0.0271 (5)	0.0306 (6)	0.0207 (5)	0.0018 (4)	0.0107 (4)	0.0003 (4)
C15	0.0235 (5)	0.0380 (7)	0.0220 (5)	0.0036 (5)	0.0072 (4)	−0.0008 (5)
C16	0.0271 (5)	0.0302 (6)	0.0183 (5)	0.0010 (4)	0.0077 (4)	0.0001 (4)
C21	0.0279 (5)	0.0313 (6)	0.0221 (5)	−0.0005 (5)	0.0115 (4)	−0.0021 (4)
C22	0.0366 (7)	0.0549 (9)	0.0268 (6)	0.0100 (6)	0.0159 (5)	0.0044 (6)
C23	0.0479 (8)	0.0624 (10)	0.0267 (6)	0.0050 (7)	0.0216 (6)	0.0004 (6)
C24	0.0436 (7)	0.0390 (7)	0.0387 (7)	−0.0023 (6)	0.0286 (6)	−0.0078 (6)
C25	0.0364 (7)	0.0469 (8)	0.0411 (8)	0.0104 (6)	0.0187 (6)	−0.0023 (6)
C26	0.0341 (6)	0.0456 (8)	0.0269 (6)	0.0074 (6)	0.0124 (5)	−0.0008 (5)
C31	0.0257 (5)	0.0408 (7)	0.0194 (5)	0.0054 (5)	0.0074 (4)	−0.0016 (5)
C32	0.0554 (9)	0.0532 (9)	0.0264 (7)	−0.0139 (7)	0.0017 (6)	0.0016 (6)
C33	0.0619 (11)	0.0666 (12)	0.0312 (8)	−0.0165 (9)	−0.0042 (7)	−0.0058 (8)
C34	0.0407 (8)	0.0827 (13)	0.0188 (6)	0.0093 (8)	0.0028 (5)	−0.0045 (7)
C35	0.0420 (8)	0.0962 (14)	0.0243 (7)	0.0009 (8)	0.0143 (6)	0.0119 (8)
C36	0.0336 (7)	0.0730 (11)	0.0255 (6)	−0.0064 (7)	0.0110 (5)	0.0056 (7)
C41	0.0255 (5)	0.0307 (6)	0.0223 (5)	0.0013 (4)	0.0095 (4)	0.0003 (4)
C42	0.0323 (6)	0.0332 (6)	0.0282 (6)	0.0015 (5)	0.0165 (5)	−0.0032 (5)
C43	0.0364 (6)	0.0282 (6)	0.0306 (6)	0.0000 (5)	0.0154 (5)	−0.0034 (5)
C44	0.0281 (6)	0.0323 (6)	0.0243 (6)	−0.0012 (5)	0.0102 (4)	0.0020 (5)
C45	0.0274 (5)	0.0346 (6)	0.0260 (6)	0.0039 (5)	0.0130 (5)	0.0006 (5)
C46	0.0277 (5)	0.0285 (6)	0.0259 (6)	0.0032 (4)	0.0109 (4)	−0.0004 (5)

F1—C24	1.3663 (14)	C21—C22	1.3917 (17)
F2—C34	1.3652 (16)	C22—C23	1.3892 (18)
O1—C1	1.2227 (16)	C22—H22	0.9500
O2—C12	1.3668 (14)	C23—C24	1.363 (2)
O2—C4	1.4269 (15)	C23—H23	0.9500
O3—C44	1.3623 (15)	C24—C25	1.369 (2)
O3—C5	1.4290 (17)	C25—C26	1.3860 (18)
C1—C2	1.4602 (17)	C25—H25	0.9500
C1—C11	1.5125 (15)	C26—H26	0.9500
C2—C3	1.3315 (18)	C31—C36	1.383 (2)
C2—H2	0.9500	C31—C32	1.390 (2)
C3—C41	1.4604 (17)	C32—C33	1.395 (2)
C3—H3	0.9500	C32—H32	0.9500
C4—H4A	0.9800	C33—C34	1.367 (3)
C4—H4B	0.9800	C33—H33	0.9500
C4—H4C	0.9800	C34—C35	1.364 (3)
C5—H5A	0.9800	C35—C36	1.392 (2)
C5—H5B	0.9800	C35—H35	0.9500
C5—H5C	0.9800	C36—H36	0.9500
C11—C16	1.3978 (16)	C41—C42	1.3919 (18)
C11—C12	1.4028 (15)	C41—C46	1.4093 (16)
C12—C13	1.3865 (16)	C42—C43	1.3894 (18)
C13—C14	1.3958 (16)	C42—H42	0.9500
C13—H13	0.9500	C43—C44	1.3909 (17)
C14—C15	1.3919 (16)	C43—H43	0.9500
C14—C21	1.4892 (16)	C44—C45	1.3955 (18)
C15—C16	1.3962 (16)	C45—C46	1.3724 (17)
C15—H15	0.9500	C45—H45	0.9500
C16—C31	1.4927 (16)	C46—H46	0.9500
C21—C26	1.3901 (18)
C12—O2—C4	116.93 (9)	C24—C23—H23	120.7
C44—O3—C5	117.47 (11)	C22—C23—H23	120.7
O1—C1—C2	120.33 (11)	C23—C24—F1	118.70 (13)
O1—C1—C11	119.44 (11)	C23—C24—C25	122.62 (12)
C2—C1—C11	120.22 (11)	F1—C24—C25	118.68 (13)
C3—C2—C1	124.49 (11)	C24—C25—C26	118.27 (13)
C3—C2—H2	117.8	C24—C25—H25	120.9
C1—C2—H2	117.8	C26—C25—H25	120.9
C2—C3—C41	126.46 (11)	C25—C26—C21	121.37 (13)
C2—C3—H3	116.8	C25—C26—H26	119.3
C41—C3—H3	116.8	C21—C26—H26	119.3
O2—C4—H4A	109.5	C36—C31—C32	118.83 (13)
O2—C4—H4B	109.5	C36—C31—C16	120.99 (12)
H4A—C4—H4B	109.5	C32—C31—C16	119.99 (12)
O2—C4—H4C	109.5	C31—C32—C33	120.81 (15)
H4A—C4—H4C	109.5	C31—C32—H32	119.6
H4B—C4—H4C	109.5	C33—C32—H32	119.6
O3—C5—H5A	109.5	C34—C33—C32	117.92 (16)
O3—C5—H5B	109.5	C34—C33—H33	121.0
H5A—C5—H5B	109.5	C32—C33—H33	121.0
O3—C5—H5C	109.5	C35—C34—F2	118.20 (16)
H5A—C5—H5C	109.5	C35—C34—C33	123.25 (14)
H5B—C5—H5C	109.5	F2—C34—C33	118.54 (17)
C16—C11—C12	118.68 (10)	C34—C35—C36	118.18 (15)
C16—C11—C1	121.93 (10)	C34—C35—H35	120.9
C12—C11—C1	119.06 (10)	C36—C35—H35	120.9
O2—C12—C13	123.33 (10)	C31—C36—C35	120.96 (15)
O2—C12—C11	115.64 (10)	C31—C36—H36	119.5
C13—C12—C11	121.01 (10)	C35—C36—H36	119.5
C12—C13—C14	120.45 (10)	C42—C41—C46	117.60 (11)
C12—C13—H13	119.8	C42—C41—C3	119.88 (11)
C14—C13—H13	119.8	C46—C41—C3	122.52 (11)
C15—C14—C13	118.60 (10)	C43—C42—C41	122.17 (11)
C15—C14—C21	121.09 (11)	C43—C42—H42	118.9
C13—C14—C21	120.28 (10)	C41—C42—H42	118.9
C14—C15—C16	121.42 (11)	C42—C43—C44	118.86 (12)
C14—C15—H15	119.3	C42—C43—H43	120.6
C16—C15—H15	119.3	C44—C43—H43	120.6
C15—C16—C11	119.80 (10)	O3—C44—C43	124.85 (12)
C15—C16—C31	117.84 (10)	O3—C44—C45	115.07 (11)
C11—C16—C31	122.33 (10)	C43—C44—C45	120.07 (11)
C26—C21—C22	118.11 (11)	C46—C45—C44	120.31 (11)
C26—C21—C14	120.76 (11)	C46—C45—H45	119.8
C22—C21—C14	121.10 (11)	C44—C45—H45	119.8
C23—C22—C21	120.97 (13)	C45—C46—C41	120.98 (12)
C23—C22—H22	119.5	C45—C46—H46	119.5
C21—C22—H22	119.5	C41—C46—H46	119.5
C24—C23—C22	118.62 (13)
O1—C1—C2—C3	−169.93 (13)	C23—C24—C25—C26	1.5 (2)
C11—C1—C2—C3	9.58 (19)	F1—C24—C25—C26	−179.01 (14)
C1—C2—C3—C41	175.54 (11)	C24—C25—C26—C21	−1.9 (2)
O1—C1—C11—C16	68.39 (16)	C22—C21—C26—C25	0.6 (2)
C2—C1—C11—C16	−111.12 (13)	C14—C21—C26—C25	178.59 (13)
O1—C1—C11—C12	−104.98 (14)	C15—C16—C31—C36	−113.39 (15)
C2—C1—C11—C12	75.50 (15)	C11—C16—C31—C36	64.74 (18)
C4—O2—C12—C13	−0.32 (18)	C15—C16—C31—C32	61.56 (18)
C4—O2—C12—C11	178.25 (12)	C11—C16—C31—C32	−120.31 (15)
C16—C11—C12—O2	−177.27 (11)	C36—C31—C32—C33	−1.6 (3)
C1—C11—C12—O2	−3.68 (16)	C16—C31—C32—C33	−176.68 (16)
C16—C11—C12—C13	1.35 (18)	C31—C32—C33—C34	0.8 (3)
C1—C11—C12—C13	174.94 (11)	C32—C33—C34—C35	1.1 (3)
O2—C12—C13—C14	178.18 (11)	C32—C33—C34—F2	179.65 (17)
C11—C12—C13—C14	−0.33 (19)	F2—C34—C35—C36	179.30 (16)
C12—C13—C14—C15	−1.26 (19)	C33—C34—C35—C36	−2.2 (3)
C12—C13—C14—C21	176.82 (12)	C32—C31—C36—C35	0.5 (2)
C13—C14—C15—C16	1.84 (19)	C16—C31—C36—C35	175.56 (14)
C21—C14—C15—C16	−176.22 (12)	C34—C35—C36—C31	1.3 (3)
C14—C15—C16—C11	−0.8 (2)	C2—C3—C41—C42	178.76 (13)
C14—C15—C16—C31	177.35 (12)	C2—C3—C41—C46	−1.5 (2)
C12—C11—C16—C15	−0.77 (18)	C46—C41—C42—C43	−0.25 (19)
C1—C11—C16—C15	−174.17 (11)	C3—C41—C42—C43	179.53 (12)
C12—C11—C16—C31	−178.86 (11)	C41—C42—C43—C44	−0.3 (2)
C1—C11—C16—C31	7.74 (18)	C5—O3—C44—C43	6.38 (19)
C15—C14—C21—C26	25.55 (19)	C5—O3—C44—C45	−172.91 (12)
C13—C14—C21—C26	−152.49 (13)	C42—C43—C44—O3	−178.15 (12)
C15—C14—C21—C22	−156.51 (13)	C42—C43—C44—C45	1.12 (19)
C13—C14—C21—C22	25.45 (19)	O3—C44—C45—C46	177.93 (11)
C26—C21—C22—C23	1.2 (2)	C43—C44—C45—C46	−1.40 (19)
C14—C21—C22—C23	−176.78 (14)	C44—C45—C46—C41	0.84 (18)
C21—C22—C23—C24	−1.6 (2)	C42—C41—C46—C45	−0.02 (18)
C22—C23—C24—F1	−179.25 (14)	C3—C41—C46—C45	−179.79 (11)
C22—C23—C24—C25	0.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···F1i	0.95	2.51	3.4159 (15)	159.
C5—H5B···O1ii	0.98	2.54	3.3534 (18)	141.
C22—H22···O1iii	0.95	2.51	3.4208 (18)	161.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯F1i	0.95	2.51	3.4159 (15)	159
C5—H5B⋯O1ii	0.98	2.54	3.3534 (18)	141
C22—H22⋯O1iii	0.95	2.51	3.4208 (18)	161

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