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

In the title compound, C(29)H(21)BrF(2)O(3), the dihedral angles between the central anisole ring and the pendant fluoro-benzene rings are 48.86 (19) and 31.89 (18)°. The dihedral angle between the anisole ring and the 1-bromo-2-meth-oxy-benzene ring linked via the enone bridge is 82.95 (17)°. In the crystal, C-H⋯O hydrogen bonds link the mol-ecules into C(11) chains propagating along [010].

Related literature

For related structures and background to chalcones and their properties, see: Fun et al. (2010 ▶).

Experimental

Crystal data

C29H21BrF2O3

M = 535.37

Monoclinic,

a = 9.6902 (6) Å

b = 20.3345 (12) Å

c = 12.9556 (8) Å

β = 110.636 (1)°

V = 2389.0 (3) Å3

Z = 4

Mo Kα radiation

μ = 1.77 mm−1

T = 296 K

0.42 × 0.15 × 0.10 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009) ▶ T min = 0.525, T max = 0.843

22747 measured reflections

5455 independent reflections

4111 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.183

S = 1.04

5455 reflections

318 parameters

H-atom parameters constrained

Δρmax = 1.96 e Å−3

Δρmin = −0.39 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811050884/hb6536sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811050884/hb6536Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811050884/hb6536Isup3.cml

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

C29H21BrF2O3	F(000) = 1088
Mr = 535.37	Dx = 1.488 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5893 reflections
a = 9.6902 (6) Å	θ = 2.3–26.7°
b = 20.3345 (12) Å	µ = 1.77 mm−1
c = 12.9556 (8) Å	T = 296 K
β = 110.636 (1)°	Block, colourless
V = 2389.0 (3) Å3	0.42 × 0.15 × 0.10 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	5455 independent reflections
Radiation source: fine-focus sealed tube	4111 reflections with I > 2σ(I)
graphite	Rint = 0.032
φ and ω scans	θmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→12
Tmin = 0.525, Tmax = 0.843	k = −26→26
22747 measured reflections	l = −16→16

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.183	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.1002P)2 + 2.471P] where P = (Fo2 + 2Fc2)/3
5455 reflections	(Δ/σ)max < 0.001
318 parameters	Δρmax = 1.96 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Br1	0.78171 (4)	0.01704 (2)	0.94057 (4)	0.05838 (18)
F1	−0.8898 (3)	0.02285 (16)	0.3378 (3)	0.0829 (9)
F2	−0.0561 (4)	0.2180 (2)	1.2026 (2)	0.0959 (11)
O1	0.0167 (3)	0.16491 (14)	0.5498 (2)	0.0466 (6)
O2	0.1325 (3)	0.24970 (13)	0.7986 (2)	0.0544 (7)
O3	0.6494 (3)	−0.11520 (13)	0.9196 (2)	0.0549 (7)
C1	−0.5661 (4)	0.0674 (2)	0.5680 (3)	0.0491 (9)
H1A	−0.5261	0.0601	0.6436	0.059*
C2	−0.7014 (5)	0.0404 (2)	0.5087 (4)	0.0576 (10)
H2A	−0.7535	0.0160	0.5435	0.069*
C3	−0.7566 (4)	0.0505 (2)	0.3978 (4)	0.0556 (10)
C4	−0.6843 (5)	0.0873 (2)	0.3442 (3)	0.0593 (11)
H4A	−0.7248	0.0932	0.2683	0.071*
C5	−0.5502 (4)	0.1154 (2)	0.4048 (3)	0.0501 (9)
H5A	−0.5012	0.1413	0.3695	0.060*
C6	−0.4877 (4)	0.10529 (17)	0.5181 (3)	0.0377 (7)
C7	−0.3388 (4)	0.13085 (16)	0.5830 (3)	0.0359 (7)
C8	−0.2327 (4)	0.13664 (16)	0.5331 (3)	0.0374 (7)
H8A	−0.2575	0.1274	0.4585	0.045*
C9	−0.0913 (4)	0.15609 (16)	0.5949 (3)	0.0352 (7)
C10	−0.0501 (4)	0.17015 (14)	0.7068 (3)	0.0334 (6)
C11	−0.1565 (4)	0.16733 (15)	0.7562 (3)	0.0343 (7)
C12	−0.2992 (4)	0.14751 (16)	0.6934 (3)	0.0370 (7)
H12A	−0.3700	0.1454	0.7265	0.044*
C13	−0.1240 (4)	0.18309 (16)	0.8754 (3)	0.0358 (7)
C14	−0.0050 (4)	0.1557 (2)	0.9580 (3)	0.0498 (9)
H14A	0.0608	0.1290	0.9396	0.060*
C15	0.0168 (5)	0.1677 (3)	1.0683 (3)	0.0655 (13)
H15A	0.0965	0.1490	1.1238	0.079*
C16	−0.0789 (5)	0.2065 (3)	1.0936 (3)	0.0594 (11)
C17	−0.1966 (5)	0.2347 (2)	1.0165 (3)	0.0594 (11)
H17A	−0.2609	0.2615	1.0366	0.071*
C18	−0.2189 (4)	0.2226 (2)	0.9060 (3)	0.0501 (9)
H18A	−0.2995	0.2414	0.8517	0.060*
C19	0.1073 (4)	0.19288 (17)	0.7681 (3)	0.0387 (7)
C20	0.2285 (4)	0.14534 (19)	0.7912 (3)	0.0448 (8)
H20A	0.3242	0.1617	0.8134	0.054*
C21	0.2106 (4)	0.08060 (18)	0.7826 (3)	0.0417 (8)
H21A	0.1137	0.0658	0.7531	0.050*
C22	0.3256 (4)	0.02905 (18)	0.8141 (3)	0.0409 (8)
C23	0.2855 (5)	−0.03641 (19)	0.8042 (3)	0.0484 (9)
H23A	0.1861	−0.0475	0.7752	0.058*
C24	0.3908 (4)	−0.08650 (18)	0.8367 (3)	0.0489 (9)
H24A	0.3613	−0.1303	0.8284	0.059*
C25	0.5372 (4)	−0.07106 (17)	0.8808 (3)	0.0421 (8)
C26	0.5802 (4)	−0.00506 (17)	0.8881 (3)	0.0383 (7)
C27	0.4753 (4)	0.04443 (16)	0.8566 (3)	0.0400 (7)
H27A	0.5050	0.0882	0.8638	0.048*
C28	−0.0242 (5)	0.1550 (3)	0.4338 (3)	0.0589 (11)
H28A	0.0605	0.1613	0.4128	0.088*
H28B	−0.0993	0.1861	0.3953	0.088*
H28C	−0.0611	0.1112	0.4154	0.088*
C29	0.6106 (6)	−0.1824 (2)	0.9226 (5)	0.0765 (16)
H29A	0.6980	−0.2078	0.9582	0.115*
H29B	0.5628	−0.1982	0.8487	0.115*
H29D	0.5447	−0.1866	0.9629	0.115*

	U11	U22	U33	U12	U13	U23
Br1	0.0392 (3)	0.0565 (3)	0.0762 (3)	−0.00361 (17)	0.0164 (2)	0.00561 (19)
F1	0.0413 (15)	0.103 (2)	0.084 (2)	−0.0160 (14)	−0.0029 (13)	−0.0303 (17)
F2	0.085 (2)	0.171 (3)	0.0257 (12)	0.012 (2)	0.0129 (12)	−0.0121 (16)
O1	0.0403 (14)	0.0676 (16)	0.0333 (12)	−0.0086 (12)	0.0147 (10)	−0.0034 (11)
O2	0.0516 (16)	0.0418 (13)	0.0579 (17)	−0.0058 (12)	0.0043 (13)	−0.0058 (12)
O3	0.0495 (16)	0.0413 (13)	0.0627 (18)	0.0056 (12)	0.0056 (13)	0.0002 (12)
C1	0.045 (2)	0.062 (2)	0.0364 (18)	−0.0089 (17)	0.0105 (16)	−0.0036 (17)
C2	0.047 (2)	0.069 (2)	0.056 (2)	−0.014 (2)	0.0173 (19)	−0.010 (2)
C3	0.0277 (18)	0.067 (3)	0.061 (3)	−0.0006 (17)	0.0009 (17)	−0.019 (2)
C4	0.042 (2)	0.084 (3)	0.038 (2)	0.007 (2)	−0.0024 (17)	−0.0061 (19)
C5	0.040 (2)	0.072 (2)	0.0331 (18)	0.0042 (18)	0.0068 (15)	0.0042 (17)
C6	0.0321 (17)	0.0477 (17)	0.0295 (16)	0.0008 (14)	0.0061 (13)	−0.0046 (14)
C7	0.0331 (17)	0.0390 (15)	0.0311 (16)	0.0017 (13)	0.0059 (13)	0.0005 (12)
C8	0.0419 (19)	0.0414 (16)	0.0268 (15)	−0.0006 (14)	0.0095 (13)	−0.0013 (13)
C9	0.0356 (17)	0.0369 (15)	0.0333 (16)	0.0004 (13)	0.0124 (13)	0.0005 (12)
C10	0.0341 (17)	0.0321 (14)	0.0296 (15)	0.0013 (12)	0.0055 (13)	0.0027 (12)
C11	0.0377 (18)	0.0340 (14)	0.0264 (15)	0.0012 (13)	0.0056 (13)	0.0014 (12)
C12	0.0354 (17)	0.0430 (16)	0.0308 (16)	0.0004 (13)	0.0094 (13)	0.0000 (13)
C13	0.0360 (17)	0.0425 (16)	0.0256 (15)	−0.0026 (13)	0.0068 (13)	0.0007 (12)
C14	0.040 (2)	0.069 (2)	0.0356 (18)	0.0120 (18)	0.0085 (15)	0.0064 (17)
C15	0.048 (2)	0.107 (4)	0.031 (2)	0.016 (2)	0.0018 (17)	0.011 (2)
C16	0.056 (2)	0.095 (3)	0.0243 (17)	−0.003 (2)	0.0115 (16)	−0.0065 (19)
C17	0.057 (3)	0.081 (3)	0.040 (2)	0.014 (2)	0.0156 (18)	−0.0076 (19)
C18	0.050 (2)	0.061 (2)	0.0320 (18)	0.0145 (18)	0.0047 (15)	−0.0016 (16)
C19	0.0379 (18)	0.0423 (17)	0.0318 (16)	−0.0030 (14)	0.0070 (13)	0.0006 (13)
C20	0.0299 (17)	0.055 (2)	0.044 (2)	0.0015 (15)	0.0064 (15)	0.0005 (16)
C21	0.0341 (18)	0.0487 (18)	0.0388 (18)	0.0025 (14)	0.0085 (14)	0.0002 (15)
C22	0.0376 (19)	0.0495 (18)	0.0340 (17)	0.0020 (15)	0.0103 (14)	0.0016 (14)
C23	0.041 (2)	0.0477 (18)	0.048 (2)	0.0005 (16)	0.0061 (16)	−0.0040 (16)
C24	0.048 (2)	0.0403 (17)	0.051 (2)	−0.0066 (16)	0.0073 (17)	−0.0069 (16)
C25	0.045 (2)	0.0394 (17)	0.0386 (18)	0.0044 (14)	0.0112 (15)	−0.0018 (14)
C26	0.0398 (18)	0.0420 (16)	0.0336 (17)	−0.0008 (14)	0.0137 (14)	0.0026 (13)
C27	0.046 (2)	0.0360 (15)	0.0387 (18)	0.0007 (14)	0.0164 (15)	0.0025 (13)
C28	0.054 (2)	0.089 (3)	0.038 (2)	−0.007 (2)	0.0220 (18)	−0.008 (2)
C29	0.070 (3)	0.039 (2)	0.089 (4)	0.002 (2)	−0.011 (3)	0.001 (2)

Br1—C26	1.882 (4)	C13—C14	1.384 (5)
F1—C3	1.370 (5)	C14—C15	1.390 (6)
F2—C16	1.370 (4)	C14—H14A	0.9300
O1—C9	1.378 (4)	C15—C16	1.344 (6)
O1—C28	1.427 (5)	C15—H15A	0.9300
O2—C19	1.218 (4)	C16—C17	1.351 (6)
O3—C25	1.362 (4)	C17—C18	1.392 (5)
O3—C29	1.422 (5)	C17—H17A	0.9300
C1—C2	1.379 (6)	C18—H18A	0.9300
C1—C6	1.390 (5)	C19—C20	1.468 (5)
C1—H1A	0.9300	C20—C21	1.327 (5)
C2—C3	1.360 (6)	C20—H20A	0.9300
C2—H2A	0.9300	C21—C22	1.479 (5)
C3—C4	1.369 (7)	C21—H21A	0.9300
C4—C5	1.383 (6)	C22—C23	1.380 (5)
C4—H4A	0.9300	C22—C27	1.394 (5)
C5—C6	1.392 (5)	C23—C24	1.398 (5)
C5—H5A	0.9300	C23—H23A	0.9300
C6—C7	1.485 (5)	C24—C25	1.366 (5)
C7—C12	1.386 (5)	C24—H24A	0.9300
C7—C8	1.398 (5)	C25—C26	1.398 (5)
C8—C9	1.379 (5)	C26—C27	1.386 (5)
C8—H8A	0.9300	C27—H27A	0.9300
C9—C10	1.391 (4)	C28—H28A	0.9600
C10—C11	1.394 (5)	C28—H28B	0.9600
C10—C19	1.522 (5)	C28—H28C	0.9600
C11—C12	1.394 (5)	C29—H29A	0.9600
C11—C13	1.498 (4)	C29—H29B	0.9600
C12—H12A	0.9300	C29—H29D	0.9600
C13—C18	1.380 (5)
C9—O1—C28	117.3 (3)	C15—C16—F2	118.5 (4)
C25—O3—C29	117.3 (3)	C17—C16—F2	118.5 (4)
C2—C1—C6	122.0 (4)	C16—C17—C18	118.0 (4)
C2—C1—H1A	119.0	C16—C17—H17A	121.0
C6—C1—H1A	119.0	C18—C17—H17A	121.0
C3—C2—C1	118.1 (4)	C13—C18—C17	121.4 (4)
C3—C2—H2A	120.9	C13—C18—H18A	119.3
C1—C2—H2A	120.9	C17—C18—H18A	119.3
C2—C3—C4	122.5 (4)	O2—C19—C20	120.3 (3)
C2—C3—F1	118.5 (4)	O2—C19—C10	120.5 (3)
C4—C3—F1	119.0 (4)	C20—C19—C10	119.3 (3)
C3—C4—C5	119.0 (4)	C21—C20—C19	124.3 (3)
C3—C4—H4A	120.5	C21—C20—H20A	117.8
C5—C4—H4A	120.5	C19—C20—H20A	117.8
C4—C5—C6	120.7 (4)	C20—C21—C22	128.0 (4)
C4—C5—H5A	119.7	C20—C21—H21A	116.0
C6—C5—H5A	119.7	C22—C21—H21A	116.0
C1—C6—C5	117.8 (3)	C23—C22—C27	118.2 (3)
C1—C6—C7	120.8 (3)	C23—C22—C21	119.9 (3)
C5—C6—C7	121.3 (3)	C27—C22—C21	121.9 (3)
C12—C7—C8	118.4 (3)	C22—C23—C24	121.6 (4)
C12—C7—C6	122.0 (3)	C22—C23—H23A	119.2
C8—C7—C6	119.6 (3)	C24—C23—H23A	119.2
C9—C8—C7	119.9 (3)	C25—C24—C23	119.9 (3)
C9—C8—H8A	120.1	C25—C24—H24A	120.0
C7—C8—H8A	120.1	C23—C24—H24A	120.0
O1—C9—C8	122.6 (3)	O3—C25—C24	125.4 (3)
O1—C9—C10	115.6 (3)	O3—C25—C26	115.3 (3)
C8—C9—C10	121.7 (3)	C24—C25—C26	119.3 (3)
C9—C10—C11	118.9 (3)	C27—C26—C25	120.5 (3)
C9—C10—C19	118.2 (3)	C27—C26—Br1	119.5 (3)
C11—C10—C19	122.7 (3)	C25—C26—Br1	120.0 (3)
C10—C11—C12	119.1 (3)	C26—C27—C22	120.4 (3)
C10—C11—C13	122.9 (3)	C26—C27—H27A	119.8
C12—C11—C13	118.0 (3)	C22—C27—H27A	119.8
C7—C12—C11	122.0 (3)	O1—C28—H28A	109.5
C7—C12—H12A	119.0	O1—C28—H28B	109.5
C11—C12—H12A	119.0	H28A—C28—H28B	109.5
C18—C13—C14	118.0 (3)	O1—C28—H28C	109.5
C18—C13—C11	120.1 (3)	H28A—C28—H28C	109.5
C14—C13—C11	121.8 (3)	H28B—C28—H28C	109.5
C13—C14—C15	120.5 (4)	O3—C29—H29A	109.5
C13—C14—H14A	119.8	O3—C29—H29B	109.5
C15—C14—H14A	119.8	H29A—C29—H29B	109.5
C16—C15—C14	119.1 (4)	O3—C29—H29D	109.5
C16—C15—H15A	120.5	H29A—C29—H29D	109.5
C14—C15—H15A	120.5	H29B—C29—H29D	109.5
C15—C16—C17	123.0 (4)
C6—C1—C2—C3	1.4 (7)	C12—C11—C13—C14	129.0 (4)
C1—C2—C3—C4	−1.4 (7)	C18—C13—C14—C15	0.2 (6)
C1—C2—C3—F1	178.8 (4)	C11—C13—C14—C15	−175.6 (4)
C2—C3—C4—C5	−0.1 (7)	C13—C14—C15—C16	−0.3 (7)
F1—C3—C4—C5	179.7 (4)	C14—C15—C16—C17	0.1 (8)
C3—C4—C5—C6	1.5 (6)	C14—C15—C16—F2	−179.9 (5)
C2—C1—C6—C5	−0.1 (6)	C15—C16—C17—C18	0.1 (8)
C2—C1—C6—C7	−176.8 (4)	F2—C16—C17—C18	−179.8 (5)
C4—C5—C6—C1	−1.4 (6)	C14—C13—C18—C17	0.0 (6)
C4—C5—C6—C7	175.3 (4)	C11—C13—C18—C17	175.9 (4)
C1—C6—C7—C12	−32.0 (5)	C16—C17—C18—C13	−0.2 (7)
C5—C6—C7—C12	151.4 (4)	C9—C10—C19—O2	108.8 (4)
C1—C6—C7—C8	146.0 (4)	C11—C10—C19—O2	−66.6 (4)
C5—C6—C7—C8	−30.6 (5)	C9—C10—C19—C20	−71.9 (4)
C12—C7—C8—C9	2.5 (5)	C11—C10—C19—C20	112.7 (4)
C6—C7—C8—C9	−175.6 (3)	O2—C19—C20—C21	165.2 (4)
C28—O1—C9—C8	1.9 (5)	C10—C19—C20—C21	−14.2 (5)
C28—O1—C9—C10	−176.1 (3)	C19—C20—C21—C22	−173.6 (3)
C7—C8—C9—O1	−177.7 (3)	C20—C21—C22—C23	176.7 (4)
C7—C8—C9—C10	0.2 (5)	C20—C21—C22—C27	−1.7 (6)
O1—C9—C10—C11	175.0 (3)	C27—C22—C23—C24	0.7 (6)
C8—C9—C10—C11	−3.0 (5)	C21—C22—C23—C24	−177.8 (4)
O1—C9—C10—C19	−0.5 (4)	C22—C23—C24—C25	0.9 (6)
C8—C9—C10—C19	−178.5 (3)	C29—O3—C25—C24	−5.3 (6)
C9—C10—C11—C12	3.0 (4)	C29—O3—C25—C26	174.8 (4)
C19—C10—C11—C12	178.4 (3)	C23—C24—C25—O3	177.1 (4)
C9—C10—C11—C13	−178.6 (3)	C23—C24—C25—C26	−3.0 (6)
C19—C10—C11—C13	−3.2 (5)	O3—C25—C26—C27	−176.6 (3)
C8—C7—C12—C11	−2.4 (5)	C24—C25—C26—C27	3.5 (5)
C6—C7—C12—C11	175.6 (3)	O3—C25—C26—Br1	3.6 (4)
C10—C11—C12—C7	−0.4 (5)	C24—C25—C26—Br1	−176.3 (3)
C13—C11—C12—C7	−178.9 (3)	C25—C26—C27—C22	−1.9 (5)
C10—C11—C13—C18	134.8 (4)	Br1—C26—C27—C22	177.9 (3)
C12—C11—C13—C18	−46.8 (5)	C23—C22—C27—C26	−0.2 (5)
C10—C11—C13—C14	−49.4 (5)	C21—C22—C27—C26	178.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C29—H29B···O2i	0.96	2.41	3.303 (6)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C29—H29B⋯O2i	0.96	2.41	3.303 (6)	155

Symmetry code: (i) .