1-(4,4''-Difluoro-5'-meth-oxy-1,1':3',1''-terphenyl-4'-yl)ethanone.

In the title compound, C(21)H(16)F(2)O(2), the central benzene ring is inclined at dihedral angles of 30.91 (8) and 46.88 (7)° to the two terminal fluoro-substituted rings. The dihedral angle between the two terminal fluoro-subsituted rings is 68.34 (8)°. An intra-molecular C-H⋯O hydrogen bond generates an S(6) ring motif. The crystal structure is stabilized by weak C-H⋯π inter-actions.

Related literature

For a related structure and background to terphenyls, see: Fun, Chia et al. (2011 ▶); Samshuddin et al. (2011 ▶). For chalcone derivatives of the title compound, see: Fun, Hemamalini et al. (2011 ▶); Betz et al. (2011 ▶). For the synthetic procedure, see: Kotnis (1990 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C21H16F2O2

M = 338.34

Monoclinic,

a = 6.0816 (7) Å

b = 25.997 (3) Å

c = 10.9061 (12) Å

β = 100.866 (2)°

V = 1693.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.74 × 0.31 × 0.10 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.930, T max = 0.990

17519 measured reflections

4923 independent reflections

2883 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.167

S = 1.03

4923 reflections

228 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.27 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/S1600536811053037/rz2681sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811053037/rz2681Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811053037/rz2681Isup3.cml

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

C21H16F2O2	F(000) = 704
Mr = 338.34	Dx = 1.327 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3484 reflections
a = 6.0816 (7) Å	θ = 2.5–24.5°
b = 25.997 (3) Å	µ = 0.10 mm−1
c = 10.9061 (12) Å	T = 296 K
β = 100.866 (2)°	Plate, colourless
V = 1693.4 (3) Å3	0.74 × 0.31 × 0.10 mm
Z = 4

Bruker APEXII DUO CCD area-detector diffractometer	4923 independent reflections
Radiation source: fine-focus sealed tube	2883 reflections with I > 2σ(I)
graphite	Rint = 0.033
φ and ω scans	θmax = 30.1°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→8
Tmin = 0.930, Tmax = 0.990	k = −33→36
17519 measured reflections	l = −15→15

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.167	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0857P)2 + 0.0565P] where P = (Fo2 + 2Fc2)/3
4923 reflections	(Δ/σ)max = 0.001
228 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.7590 (3)	0.93216 (6)	0.59950 (13)	0.1136 (5)
F2	−0.8096 (2)	1.00075 (4)	−0.25890 (13)	0.0932 (4)
O1	0.0345 (2)	0.73907 (4)	0.00260 (11)	0.0617 (3)
O2	−0.4540 (2)	0.77193 (5)	−0.13608 (13)	0.0825 (4)
C1	0.2502 (3)	0.91677 (6)	0.37217 (14)	0.0527 (4)
H1A	0.1061	0.9302	0.3545	0.063*
C2	0.3999 (3)	0.93447 (7)	0.47550 (16)	0.0647 (5)
H2A	0.3569	0.9592	0.5279	0.078*
C3	0.6109 (4)	0.91488 (7)	0.49859 (17)	0.0705 (5)
C4	0.6816 (3)	0.87831 (8)	0.42537 (18)	0.0711 (5)
H4A	0.8267	0.8655	0.4444	0.085*
C5	0.5325 (3)	0.86066 (6)	0.32199 (15)	0.0586 (4)
H5A	0.5795	0.8362	0.2703	0.070*
C6	0.3128 (3)	0.87898 (5)	0.29407 (13)	0.0456 (3)
C7	0.1516 (2)	0.85840 (5)	0.18611 (13)	0.0457 (3)
C8	0.1709 (3)	0.80732 (6)	0.14915 (13)	0.0502 (4)
H8A	0.2819	0.7863	0.1935	0.060*
C9	0.0255 (3)	0.78806 (5)	0.04698 (14)	0.0493 (3)
C10	−0.1469 (3)	0.81858 (5)	−0.01979 (13)	0.0467 (3)
C11	−0.1702 (2)	0.86946 (5)	0.01721 (13)	0.0455 (3)
C12	−0.0200 (2)	0.88852 (5)	0.12041 (13)	0.0465 (3)
H12A	−0.0354	0.9223	0.1457	0.056*
C13	−0.3440 (2)	0.90439 (5)	−0.05353 (12)	0.0454 (3)
C14	−0.5668 (3)	0.88925 (6)	−0.08926 (16)	0.0573 (4)
H14A	−0.6106	0.8570	−0.0661	0.069*
C15	−0.7240 (3)	0.92160 (7)	−0.15882 (17)	0.0660 (5)
H15A	−0.8721	0.9112	−0.1837	0.079*
C16	−0.6553 (3)	0.96922 (7)	−0.18989 (15)	0.0612 (4)
C17	−0.4413 (3)	0.98642 (6)	−0.15416 (16)	0.0610 (4)
H17A	−0.4010	1.0194	−0.1748	0.073*
C18	−0.2853 (3)	0.95354 (6)	−0.08626 (14)	0.0525 (4)
H18A	−0.1380	0.9645	−0.0619	0.063*
C19	0.2322 (3)	0.70987 (6)	0.04690 (18)	0.0668 (5)
H19A	0.2267	0.6783	0.0007	0.100*
H19B	0.2417	0.7023	0.1339	0.100*
H19C	0.3612	0.7293	0.0359	0.100*
C20	−0.2837 (3)	0.79540 (6)	−0.13640 (15)	0.0548 (4)
C21	−0.1930 (4)	0.80270 (11)	−0.25154 (18)	0.0997 (8)
H21A	−0.2653	0.7793	−0.3146	0.150*
H21B	−0.0348	0.7961	−0.2344	0.150*
H21C	−0.2198	0.8374	−0.2805	0.150*

	U11	U22	U33	U12	U13	U23
F1	0.1147 (10)	0.1119 (10)	0.0921 (9)	−0.0152 (8)	−0.0369 (8)	−0.0252 (8)
F2	0.0933 (8)	0.0800 (8)	0.0952 (9)	0.0405 (6)	−0.0111 (7)	0.0045 (6)
O1	0.0756 (8)	0.0373 (6)	0.0671 (7)	0.0058 (5)	0.0004 (6)	−0.0108 (5)
O2	0.0853 (9)	0.0775 (9)	0.0815 (9)	−0.0340 (7)	0.0074 (7)	−0.0082 (7)
C1	0.0663 (9)	0.0407 (8)	0.0495 (8)	−0.0009 (7)	0.0069 (7)	0.0013 (6)
C2	0.0898 (13)	0.0491 (9)	0.0520 (9)	−0.0063 (9)	0.0056 (9)	−0.0073 (7)
C3	0.0818 (12)	0.0611 (11)	0.0591 (10)	−0.0144 (9)	−0.0106 (9)	−0.0027 (8)
C4	0.0575 (10)	0.0697 (12)	0.0788 (12)	−0.0044 (8)	−0.0055 (9)	0.0030 (10)
C5	0.0603 (9)	0.0524 (9)	0.0618 (9)	−0.0009 (7)	0.0084 (8)	−0.0030 (7)
C6	0.0576 (8)	0.0351 (7)	0.0433 (7)	−0.0028 (6)	0.0072 (6)	0.0044 (5)
C7	0.0572 (8)	0.0358 (7)	0.0439 (7)	−0.0007 (6)	0.0092 (6)	0.0012 (5)
C8	0.0618 (9)	0.0367 (7)	0.0497 (8)	0.0041 (6)	0.0046 (7)	0.0008 (6)
C9	0.0628 (9)	0.0340 (7)	0.0509 (8)	−0.0001 (6)	0.0101 (7)	−0.0020 (6)
C10	0.0559 (8)	0.0383 (7)	0.0458 (7)	−0.0034 (6)	0.0096 (6)	−0.0011 (6)
C11	0.0513 (8)	0.0387 (7)	0.0465 (7)	−0.0005 (6)	0.0095 (6)	0.0010 (6)
C12	0.0578 (8)	0.0349 (7)	0.0461 (7)	0.0025 (6)	0.0079 (6)	−0.0026 (5)
C13	0.0528 (8)	0.0404 (7)	0.0440 (7)	0.0030 (6)	0.0118 (6)	−0.0010 (6)
C14	0.0554 (9)	0.0489 (9)	0.0683 (10)	−0.0005 (7)	0.0137 (8)	0.0020 (7)
C15	0.0510 (9)	0.0665 (12)	0.0785 (11)	0.0080 (8)	0.0067 (8)	−0.0084 (9)
C16	0.0680 (10)	0.0585 (10)	0.0543 (9)	0.0224 (8)	0.0044 (8)	−0.0016 (8)
C17	0.0752 (11)	0.0441 (9)	0.0651 (10)	0.0090 (8)	0.0171 (9)	0.0089 (7)
C18	0.0545 (8)	0.0444 (8)	0.0586 (9)	0.0012 (6)	0.0106 (7)	0.0015 (7)
C19	0.0764 (11)	0.0456 (9)	0.0781 (12)	0.0123 (8)	0.0141 (9)	−0.0103 (8)
C20	0.0607 (9)	0.0445 (8)	0.0571 (9)	−0.0012 (7)	0.0057 (7)	−0.0054 (7)
C21	0.0960 (16)	0.145 (2)	0.0591 (11)	−0.0280 (15)	0.0183 (11)	−0.0237 (13)

F1—C3	1.360 (2)	C10—C20	1.508 (2)
F2—C16	1.3610 (19)	C11—C12	1.3997 (19)
O1—C9	1.3671 (17)	C11—C13	1.4930 (19)
O1—C19	1.427 (2)	C12—H12A	0.9300
O2—C20	1.203 (2)	C13—C18	1.391 (2)
C1—C2	1.387 (2)	C13—C14	1.394 (2)
C1—C6	1.399 (2)	C14—C15	1.387 (2)
C1—H1A	0.9300	C14—H14A	0.9300
C2—C3	1.359 (3)	C15—C16	1.369 (3)
C2—H2A	0.9300	C15—H15A	0.9300
C3—C4	1.362 (3)	C16—C17	1.362 (3)
C4—C5	1.385 (2)	C17—C18	1.383 (2)
C4—H4A	0.9300	C17—H17A	0.9300
C5—C6	1.397 (2)	C18—H18A	0.9300
C5—H5A	0.9300	C19—H19A	0.9600
C6—C7	1.483 (2)	C19—H19B	0.9600
C7—C12	1.3904 (19)	C19—H19C	0.9600
C7—C8	1.399 (2)	C20—C21	1.476 (3)
C8—C9	1.379 (2)	C21—H21A	0.9600
C8—H8A	0.9300	C21—H21B	0.9600
C9—C10	1.404 (2)	C21—H21C	0.9600
C10—C11	1.398 (2)
C9—O1—C19	117.60 (12)	C7—C12—H12A	119.1
C2—C1—C6	121.04 (16)	C11—C12—H12A	119.1
C2—C1—H1A	119.5	C18—C13—C14	118.05 (14)
C6—C1—H1A	119.5	C18—C13—C11	120.02 (13)
C3—C2—C1	118.57 (17)	C14—C13—C11	121.93 (13)
C3—C2—H2A	120.7	C15—C14—C13	121.03 (16)
C1—C2—H2A	120.7	C15—C14—H14A	119.5
C2—C3—F1	118.96 (19)	C13—C14—H14A	119.5
C2—C3—C4	122.96 (16)	C16—C15—C14	118.18 (16)
F1—C3—C4	118.09 (19)	C16—C15—H15A	120.9
C3—C4—C5	118.56 (18)	C14—C15—H15A	120.9
C3—C4—H4A	120.7	F2—C16—C17	118.85 (16)
C5—C4—H4A	120.7	F2—C16—C15	118.08 (17)
C4—C5—C6	121.13 (16)	C17—C16—C15	123.08 (15)
C4—C5—H5A	119.4	C16—C17—C18	118.17 (16)
C6—C5—H5A	119.4	C16—C17—H17A	120.9
C5—C6—C1	117.73 (14)	C18—C17—H17A	120.9
C5—C6—C7	120.81 (13)	C17—C18—C13	121.45 (15)
C1—C6—C7	121.46 (14)	C17—C18—H18A	119.3
C12—C7—C8	118.78 (13)	C13—C18—H18A	119.3
C12—C7—C6	121.72 (12)	O1—C19—H19A	109.5
C8—C7—C6	119.49 (13)	O1—C19—H19B	109.5
C9—C8—C7	120.08 (14)	H19A—C19—H19B	109.5
C9—C8—H8A	120.0	O1—C19—H19C	109.5
C7—C8—H8A	120.0	H19A—C19—H19C	109.5
O1—C9—C8	124.16 (14)	H19B—C19—H19C	109.5
O1—C9—C10	114.76 (13)	O2—C20—C21	121.87 (16)
C8—C9—C10	121.08 (13)	O2—C20—C10	122.61 (15)
C11—C10—C9	119.45 (13)	C21—C20—C10	115.52 (15)
C11—C10—C20	123.47 (13)	C20—C21—H21A	109.5
C9—C10—C20	116.81 (12)	C20—C21—H21B	109.5
C10—C11—C12	118.71 (13)	H21A—C21—H21B	109.5
C10—C11—C13	121.79 (13)	C20—C21—H21C	109.5
C12—C11—C13	119.44 (12)	H21A—C21—H21C	109.5
C7—C12—C11	121.86 (13)	H21B—C21—H21C	109.5
C6—C1—C2—C3	1.0 (3)	C20—C10—C11—C12	−173.84 (14)
C1—C2—C3—F1	179.78 (16)	C9—C10—C11—C13	177.29 (14)
C1—C2—C3—C4	−0.5 (3)	C20—C10—C11—C13	3.5 (2)
C2—C3—C4—C5	0.7 (3)	C8—C7—C12—C11	−1.3 (2)
F1—C3—C4—C5	−179.64 (17)	C6—C7—C12—C11	178.96 (14)
C3—C4—C5—C6	−1.3 (3)	C10—C11—C12—C7	0.4 (2)
C4—C5—C6—C1	1.7 (2)	C13—C11—C12—C7	−176.95 (13)
C4—C5—C6—C7	−177.57 (15)	C10—C11—C13—C18	−131.38 (16)
C2—C1—C6—C5	−1.6 (2)	C12—C11—C13—C18	45.89 (19)
C2—C1—C6—C7	177.70 (14)	C10—C11—C13—C14	48.3 (2)
C5—C6—C7—C12	−149.43 (15)	C12—C11—C13—C14	−134.44 (16)
C1—C6—C7—C12	31.3 (2)	C18—C13—C14—C15	2.0 (2)
C5—C6—C7—C8	30.9 (2)	C11—C13—C14—C15	−177.66 (14)
C1—C6—C7—C8	−148.36 (15)	C13—C14—C15—C16	−1.0 (3)
C12—C7—C8—C9	1.9 (2)	C14—C15—C16—F2	179.55 (15)
C6—C7—C8—C9	−178.40 (14)	C14—C15—C16—C17	−1.0 (3)
C19—O1—C9—C8	−14.0 (2)	F2—C16—C17—C18	−178.69 (14)
C19—O1—C9—C10	166.16 (14)	C15—C16—C17—C18	1.8 (3)
C7—C8—C9—O1	178.61 (14)	C16—C17—C18—C13	−0.7 (2)
C7—C8—C9—C10	−1.5 (2)	C14—C13—C18—C17	−1.1 (2)
O1—C9—C10—C11	−179.55 (13)	C11—C13—C18—C17	178.55 (14)
C8—C9—C10—C11	0.6 (2)	C11—C10—C20—O2	−93.9 (2)
O1—C9—C10—C20	−5.3 (2)	C9—C10—C20—O2	92.1 (2)
C8—C9—C10—C20	174.82 (15)	C11—C10—C20—C21	87.0 (2)
C9—C10—C11—C12	0.0 (2)	C9—C10—C20—C21	−87.0 (2)

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···O2	0.93	2.58	3.188 (2)	124.
C19—H19A···Cg1i	0.96	2.80	3.6432 (19)	147.

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14A⋯O2	0.93	2.58	3.188 (2)	124
C19—H19A⋯Cg1i	0.96	2.80	3.6432 (19)	147

Symmetry code: (i) .