(2E)-3-(2-Bromo-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(28)H(19)BrF(2)O(2), the central benzene ring makes dihedral angles of 62.51 (18), 46.23 (18) and 48.19 (18)° with the bromo-substituted benzene ring and two terminal fluoro-substituted benzene rings, respectively. In the crystal, mol-ecules are linked by C-H⋯F hydrogen bonds into infinite chains along [110]. Weak C-H⋯π and π-π inter-actions [centroid-centroid distance = 3.683 (2) Å] also occur and short inter-molecular F⋯F contacts [2.833 (4) Å] are observed.

Related literature

For related structures and background to terphenyl chalcones, see: Fun et al. (2011a ▶,b ▶, 2012 ▶). For reference bond lengths, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C28H19BrF2O2

M = 505.34

Monoclinic,

a = 22.4861 (6) Å

b = 6.9006 (2) Å

c = 28.6933 (8) Å

β = 101.286 (2)°

V = 4366.2 (2) Å3

Z = 8

Mo Kα radiation

μ = 1.92 mm−1

T = 100 K

0.37 × 0.12 × 0.08 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.533, T max = 0.863

24190 measured reflections

6414 independent reflections

4483 reflections with I > 2σ(I)

R int = 0.076

Refinement

R[F 2 > 2σ(F 2)] = 0.071

wR(F 2) = 0.134

S = 1.11

6414 reflections

299 parameters

H-atom parameters constrained

Δρmax = 0.72 e Å−3

Δρmin = −1.09 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/S1600536812013852/hb6704sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812013852/hb6704Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812013852/hb6704Isup3.cml

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

C28H19BrF2O2	F(000) = 2048
Mr = 505.34	Dx = 1.538 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4738 reflections
a = 22.4861 (6) Å	θ = 2.6–29.4°
b = 6.9006 (2) Å	µ = 1.92 mm−1
c = 28.6933 (8) Å	T = 100 K
β = 101.286 (2)°	Needle, colourless
V = 4366.2 (2) Å3	0.37 × 0.12 × 0.08 mm
Z = 8

Bruker SMART APEXII CCD diffractometer	6414 independent reflections
Radiation source: fine-focus sealed tube	4483 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.076
φ and ω scans	θmax = 30.3°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −31→23
Tmin = 0.533, Tmax = 0.863	k = −9→9
24190 measured reflections	l = −40→39

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)] = 0.071	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.0321P)2 + 25.8799P] where P = (Fo2 + 2Fc2)/3
6414 reflections	(Δ/σ)max < 0.001
299 parameters	Δρmax = 0.72 e Å−3
0 restraints	Δρmin = −1.09 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
F1	0.05500 (11)	1.3787 (4)	0.23294 (8)	0.0264 (6)
F2	−0.34855 (10)	0.4660 (3)	−0.01133 (9)	0.0242 (5)
Br1	0.327887 (17)	0.59947 (6)	0.161236 (15)	0.02040 (11)
O1	0.04875 (11)	0.3643 (4)	0.05277 (10)	0.0186 (6)
O2	0.11379 (12)	0.8145 (4)	0.10429 (10)	0.0227 (6)
C1	0.29189 (17)	0.3696 (6)	0.17939 (13)	0.0164 (8)
C2	0.32983 (18)	0.2283 (6)	0.20296 (13)	0.0205 (9)
H2A	0.3716	0.2470	0.2094	0.025*
C3	0.30549 (19)	0.0591 (6)	0.21700 (15)	0.0235 (9)
H3A	0.3308	−0.0355	0.2333	0.028*
C4	0.2435 (2)	0.0309 (6)	0.20675 (16)	0.0252 (10)
H4A	0.2271	−0.0833	0.2160	0.030*
C5	0.20594 (18)	0.1712 (6)	0.18288 (15)	0.0217 (9)
H5A	0.1644	0.1484	0.1755	0.026*
C6	0.22854 (17)	0.3485 (6)	0.16924 (14)	0.0175 (8)
C7	0.18826 (17)	0.5015 (6)	0.14592 (14)	0.0171 (8)
H7A	0.2064	0.6160	0.1389	0.020*
C8	0.12818 (16)	0.4921 (6)	0.13392 (14)	0.0162 (8)
H8A	0.1087	0.3784	0.1398	0.019*
C9	0.09102 (16)	0.6582 (6)	0.11128 (14)	0.0152 (8)
C10	0.02379 (15)	0.6264 (5)	0.09697 (13)	0.0134 (7)
C11	−0.01873 (16)	0.7463 (5)	0.11261 (13)	0.0132 (7)
C12	−0.08046 (16)	0.7099 (5)	0.09609 (13)	0.0131 (7)
H12A	−0.1089	0.7873	0.1068	0.016*
C13	−0.10049 (16)	0.5610 (5)	0.06407 (13)	0.0130 (7)
C14	−0.05778 (16)	0.4412 (5)	0.04891 (13)	0.0140 (8)
H14A	−0.0705	0.3409	0.0277	0.017*
C15	0.00371 (16)	0.4725 (6)	0.06567 (14)	0.0149 (8)
C16	−0.00013 (15)	0.9085 (6)	0.14622 (13)	0.0149 (7)
C17	0.04441 (17)	0.8892 (6)	0.18743 (14)	0.0195 (8)
H17A	0.0624	0.7691	0.1952	0.023*
C18	0.06198 (17)	1.0457 (6)	0.21673 (14)	0.0183 (8)
H18A	0.0915	1.0315	0.2442	0.022*
C19	0.03536 (17)	1.2232 (6)	0.20488 (14)	0.0168 (8)
C20	−0.01063 (17)	1.2479 (6)	0.16598 (14)	0.0170 (8)
H20A	−0.0298	1.3671	0.1596	0.020*
C21	−0.02756 (15)	1.0898 (6)	0.13661 (13)	0.0146 (7)
H21A	−0.0580	1.1046	0.1098	0.018*
C22	−0.16673 (16)	0.5323 (5)	0.04452 (13)	0.0129 (7)
C23	−0.18668 (17)	0.5112 (6)	−0.00430 (14)	0.0167 (8)
H23A	−0.1588	0.5115	−0.0243	0.020*
C24	−0.24795 (17)	0.4900 (5)	−0.02318 (14)	0.0172 (8)
H24A	−0.2616	0.4772	−0.0558	0.021*
C25	−0.28826 (17)	0.4882 (6)	0.00758 (15)	0.0176 (8)
C26	−0.27040 (17)	0.5068 (6)	0.05564 (15)	0.0182 (8)
H26A	−0.2986	0.5034	0.0754	0.022*
C27	−0.20866 (17)	0.5311 (5)	0.07448 (14)	0.0150 (8)
H27A	−0.1955	0.5466	0.1071	0.018*
C28	0.03253 (18)	0.1869 (6)	0.02761 (15)	0.0206 (9)
H28A	0.0686	0.1224	0.0226	0.031*
H28B	0.0068	0.2145	−0.0025	0.031*
H28C	0.0113	0.1049	0.0459	0.031*

	U11	U22	U33	U12	U13	U23
F1	0.0268 (13)	0.0204 (13)	0.0315 (14)	−0.0099 (11)	0.0043 (10)	−0.0100 (11)
F2	0.0090 (10)	0.0241 (13)	0.0374 (14)	0.0011 (9)	−0.0004 (10)	−0.0055 (11)
Br1	0.00986 (16)	0.0217 (2)	0.0293 (2)	−0.00161 (18)	0.00283 (13)	−0.00163 (19)
O1	0.0135 (12)	0.0155 (14)	0.0275 (15)	0.0042 (11)	0.0056 (11)	−0.0053 (11)
O2	0.0125 (13)	0.0180 (15)	0.0377 (18)	0.0013 (12)	0.0054 (12)	0.0066 (13)
C1	0.0171 (18)	0.017 (2)	0.0142 (18)	0.0018 (15)	0.0005 (14)	−0.0030 (15)
C2	0.0183 (19)	0.026 (2)	0.015 (2)	0.0079 (17)	−0.0029 (15)	−0.0044 (17)
C3	0.028 (2)	0.019 (2)	0.023 (2)	0.0101 (18)	0.0023 (17)	0.0017 (17)
C4	0.028 (2)	0.016 (2)	0.033 (3)	0.0005 (18)	0.0101 (19)	0.0042 (18)
C5	0.0141 (18)	0.019 (2)	0.033 (2)	0.0015 (16)	0.0076 (17)	0.0045 (18)
C6	0.0157 (18)	0.016 (2)	0.020 (2)	0.0028 (15)	0.0029 (15)	0.0022 (15)
C7	0.0131 (17)	0.018 (2)	0.021 (2)	0.0006 (16)	0.0046 (15)	0.0023 (16)
C8	0.0104 (17)	0.018 (2)	0.022 (2)	−0.0023 (15)	0.0057 (15)	0.0029 (16)
C9	0.0111 (17)	0.0147 (19)	0.022 (2)	0.0018 (14)	0.0080 (15)	0.0003 (15)
C10	0.0082 (15)	0.0132 (19)	0.0184 (19)	−0.0001 (14)	0.0017 (13)	0.0036 (15)
C11	0.0102 (16)	0.0144 (19)	0.0146 (18)	0.0022 (14)	0.0013 (14)	0.0022 (15)
C12	0.0115 (16)	0.0111 (18)	0.0176 (19)	0.0017 (15)	0.0051 (14)	0.0014 (14)
C13	0.0132 (16)	0.0105 (18)	0.0148 (18)	−0.0021 (14)	0.0015 (14)	0.0005 (14)
C14	0.0137 (17)	0.0102 (19)	0.0181 (19)	0.0008 (14)	0.0034 (14)	−0.0004 (14)
C15	0.0097 (16)	0.0136 (18)	0.022 (2)	0.0015 (14)	0.0060 (15)	0.0028 (15)
C16	0.0113 (16)	0.0156 (18)	0.0192 (19)	−0.0009 (16)	0.0064 (14)	0.0009 (16)
C17	0.0166 (18)	0.017 (2)	0.024 (2)	0.0006 (17)	0.0023 (15)	−0.0001 (17)
C18	0.0131 (17)	0.021 (2)	0.019 (2)	−0.0023 (16)	−0.0007 (15)	0.0005 (16)
C19	0.0161 (18)	0.0149 (19)	0.021 (2)	−0.0087 (16)	0.0068 (15)	−0.0065 (16)
C20	0.0149 (18)	0.0127 (19)	0.026 (2)	−0.0039 (15)	0.0109 (16)	0.0009 (16)
C21	0.0098 (15)	0.0173 (19)	0.0176 (18)	0.0006 (16)	0.0044 (13)	0.0006 (16)
C22	0.0104 (16)	0.0082 (17)	0.020 (2)	−0.0028 (14)	0.0026 (14)	−0.0002 (14)
C23	0.0154 (18)	0.0137 (19)	0.021 (2)	0.0025 (15)	0.0041 (15)	−0.0013 (16)
C24	0.0182 (19)	0.0120 (19)	0.019 (2)	0.0019 (16)	−0.0017 (16)	−0.0011 (15)
C25	0.0112 (17)	0.0096 (18)	0.030 (2)	0.0011 (15)	−0.0007 (16)	−0.0008 (16)
C26	0.0128 (18)	0.016 (2)	0.027 (2)	−0.0007 (16)	0.0084 (16)	−0.0004 (17)
C27	0.0150 (18)	0.0113 (18)	0.018 (2)	0.0007 (15)	0.0027 (15)	−0.0013 (15)
C28	0.0177 (19)	0.017 (2)	0.028 (2)	0.0032 (16)	0.0070 (17)	−0.0049 (17)

F1—C19	1.362 (4)	C13—C14	1.400 (5)
F2—C25	1.366 (4)	C13—C22	1.499 (5)
Br1—C1	1.899 (4)	C14—C15	1.389 (5)
O1—C15	1.366 (4)	C14—H14A	0.9300
O1—C28	1.432 (5)	C16—C21	1.398 (5)
O2—C9	1.227 (5)	C16—C17	1.398 (5)
C1—C2	1.382 (5)	C17—C18	1.378 (6)
C1—C6	1.405 (5)	C17—H17A	0.9300
C2—C3	1.383 (6)	C18—C19	1.377 (6)
C2—H2A	0.9300	C18—H18A	0.9300
C3—C4	1.380 (6)	C19—C20	1.375 (5)
C3—H3A	0.9300	C20—C21	1.386 (5)
C4—C5	1.377 (6)	C20—H20A	0.9300
C4—H4A	0.9300	C21—H21A	0.9300
C5—C6	1.409 (6)	C22—C23	1.392 (5)
C5—H5A	0.9300	C22—C27	1.395 (5)
C6—C7	1.465 (5)	C23—C24	1.386 (5)
C7—C8	1.329 (5)	C23—H23A	0.9300
C7—H7A	0.9300	C24—C25	1.384 (6)
C8—C9	1.490 (5)	C24—H24A	0.9300
C8—H8A	0.9300	C25—C26	1.365 (6)
C9—C10	1.503 (5)	C26—C27	1.398 (5)
C10—C11	1.403 (5)	C26—H26A	0.9300
C10—C15	1.407 (5)	C27—H27A	0.9300
C11—C12	1.399 (5)	C28—H28A	0.9600
C11—C16	1.483 (5)	C28—H28B	0.9600
C12—C13	1.393 (5)	C28—H28C	0.9600
C12—H12A	0.9300
C15—O1—C28	118.3 (3)	O1—C15—C10	115.0 (3)
C2—C1—C6	122.1 (4)	C14—C15—C10	120.8 (3)
C2—C1—Br1	117.9 (3)	C21—C16—C17	117.9 (4)
C6—C1—Br1	120.0 (3)	C21—C16—C11	119.3 (3)
C1—C2—C3	119.8 (4)	C17—C16—C11	122.8 (4)
C1—C2—H2A	120.1	C18—C17—C16	120.9 (4)
C3—C2—H2A	120.1	C18—C17—H17A	119.6
C4—C3—C2	119.8 (4)	C16—C17—H17A	119.6
C4—C3—H3A	120.1	C19—C18—C17	119.2 (4)
C2—C3—H3A	120.1	C19—C18—H18A	120.4
C5—C4—C3	120.2 (4)	C17—C18—H18A	120.4
C5—C4—H4A	119.9	F1—C19—C20	119.2 (4)
C3—C4—H4A	119.9	F1—C19—C18	118.7 (3)
C4—C5—C6	122.0 (4)	C20—C19—C18	122.1 (4)
C4—C5—H5A	119.0	C19—C20—C21	118.0 (4)
C6—C5—H5A	119.0	C19—C20—H20A	121.0
C1—C6—C5	116.0 (3)	C21—C20—H20A	121.0
C1—C6—C7	122.1 (4)	C20—C21—C16	121.8 (3)
C5—C6—C7	121.9 (3)	C20—C21—H21A	119.1
C8—C7—C6	126.1 (4)	C16—C21—H21A	119.1
C8—C7—H7A	116.9	C23—C22—C27	119.7 (3)
C6—C7—H7A	116.9	C23—C22—C13	119.4 (3)
C7—C8—C9	122.0 (4)	C27—C22—C13	120.8 (3)
C7—C8—H8A	119.0	C24—C23—C22	120.3 (4)
C9—C8—H8A	119.0	C24—C23—H23A	119.9
O2—C9—C8	122.1 (3)	C22—C23—H23A	119.9
O2—C9—C10	120.9 (3)	C25—C24—C23	118.5 (4)
C8—C9—C10	117.0 (3)	C25—C24—H24A	120.8
C11—C10—C15	119.7 (3)	C23—C24—H24A	120.8
C11—C10—C9	122.6 (3)	C26—C25—F2	119.0 (3)
C15—C10—C9	117.7 (3)	C26—C25—C24	122.9 (4)
C12—C11—C10	118.6 (3)	F2—C25—C24	118.1 (3)
C12—C11—C16	119.4 (3)	C25—C26—C27	118.4 (4)
C10—C11—C16	122.0 (3)	C25—C26—H26A	120.8
C13—C12—C11	121.8 (3)	C27—C26—H26A	120.8
C13—C12—H12A	119.1	C22—C27—C26	120.1 (4)
C11—C12—H12A	119.1	C22—C27—H27A	119.9
C12—C13—C14	119.2 (3)	C26—C27—H27A	119.9
C12—C13—C22	120.9 (3)	O1—C28—H28A	109.5
C14—C13—C22	119.8 (3)	O1—C28—H28B	109.5
C15—C14—C13	119.9 (3)	H28A—C28—H28B	109.5
C15—C14—H14A	120.1	O1—C28—H28C	109.5
C13—C14—H14A	120.1	H28A—C28—H28C	109.5
O1—C15—C14	124.2 (3)	H28B—C28—H28C	109.5
C6—C1—C2—C3	0.4 (6)	C13—C14—C15—C10	−1.5 (6)
Br1—C1—C2—C3	179.7 (3)	C11—C10—C15—O1	−179.8 (3)
C1—C2—C3—C4	1.0 (6)	C9—C10—C15—O1	1.8 (5)
C2—C3—C4—C5	−0.4 (6)	C11—C10—C15—C14	1.9 (6)
C3—C4—C5—C6	−1.7 (7)	C9—C10—C15—C14	−176.4 (3)
C2—C1—C6—C5	−2.4 (6)	C12—C11—C16—C21	−47.1 (5)
Br1—C1—C6—C5	178.4 (3)	C10—C11—C16—C21	133.3 (4)
C2—C1—C6—C7	177.6 (4)	C12—C11—C16—C17	133.3 (4)
Br1—C1—C6—C7	−1.7 (5)	C10—C11—C16—C17	−46.2 (5)
C4—C5—C6—C1	3.0 (6)	C21—C16—C17—C18	−2.1 (6)
C4—C5—C6—C7	−176.9 (4)	C11—C16—C17—C18	177.5 (4)
C1—C6—C7—C8	178.2 (4)	C16—C17—C18—C19	−0.4 (6)
C5—C6—C7—C8	−1.9 (7)	C17—C18—C19—F1	−177.1 (3)
C6—C7—C8—C9	178.5 (4)	C17—C18—C19—C20	3.5 (6)
C7—C8—C9—O2	−2.9 (6)	F1—C19—C20—C21	176.6 (3)
C7—C8—C9—C10	176.8 (4)	C18—C19—C20—C21	−4.0 (6)
O2—C9—C10—C11	−55.4 (5)	C19—C20—C21—C16	1.3 (5)
C8—C9—C10—C11	124.8 (4)	C17—C16—C21—C20	1.6 (5)
O2—C9—C10—C15	122.9 (4)	C11—C16—C21—C20	−178.0 (3)
C8—C9—C10—C15	−56.9 (5)	C12—C13—C22—C23	130.6 (4)
C15—C10—C11—C12	−0.6 (5)	C14—C13—C22—C23	−47.2 (5)
C9—C10—C11—C12	177.7 (3)	C12—C13—C22—C27	−47.8 (5)
C15—C10—C11—C16	179.0 (3)	C14—C13—C22—C27	134.4 (4)
C9—C10—C11—C16	−2.7 (6)	C27—C22—C23—C24	0.2 (6)
C10—C11—C12—C13	−1.2 (5)	C13—C22—C23—C24	−178.2 (3)
C16—C11—C12—C13	179.2 (3)	C22—C23—C24—C25	−0.7 (6)
C11—C12—C13—C14	1.7 (5)	C23—C24—C25—C26	0.1 (6)
C11—C12—C13—C22	−176.2 (3)	C23—C24—C25—F2	−179.6 (3)
C12—C13—C14—C15	−0.3 (5)	F2—C25—C26—C27	−179.4 (3)
C22—C13—C14—C15	177.6 (3)	C24—C25—C26—C27	0.8 (6)
C28—O1—C15—C14	−12.1 (5)	C23—C22—C27—C26	0.7 (6)
C28—O1—C15—C10	169.7 (3)	C13—C22—C27—C26	179.1 (3)
C13—C14—C15—O1	−179.6 (3)	C25—C26—C27—C22	−1.2 (6)

D—H···A	D—H	H···A	D···A	D—H···A
C28—H28A···F2i	0.96	2.51	3.448 (4)	166
C4—H4A···Cg1ii	0.93	2.99	3.712 (5)	136
C20—H20A···Cg2iii	0.93	2.72	3.383 (4)	129
C27—H27A···Cg1iv	0.93	2.95	3.735 (4)	143
C28—H28B···Cg2v	0.96	2.82	3.485 (4)	128

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of C1—C6 and C10—C15 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C28—H28A⋯F2i	0.96	2.51	3.448 (4)	166
C4—H4A⋯Cg1ii	0.93	2.99	3.712 (5)	136
C20—H20A⋯Cg2iii	0.93	2.72	3.383 (4)	129
C27—H27A⋯Cg1iv	0.93	2.95	3.735 (4)	143
C28—H28B⋯Cg2v	0.96	2.82	3.485 (4)	128

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