(2E)-1-(4,4′′-Difluoro-5′-meth­oxy-1,1′:3′,1′′-terphenyl-4′-yl)-3-(2,6-difluoro­phen­yl)prop-2-en-1-one

Fun, H.-K.; Chia, T.S.; Samshuddin, S.; Narayana, B.; Sarojini, B.K.

doi:10.1107/S160053681201820X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 5| May 2012| Pages o1560-o1561

doi:10.1107/S160053681201820X

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(2E)-1-(4,4′′-Difluoro-5′-methoxy-1,1′:3′,1′′-terphenyl-4′-yl)-3-(2,6-difluorophenyl)prop-2-en-1-one

Hoong-Kun Fun,^a ^*‡ Tze Shyang Chia,^a S. Samshuddin,^b B. Narayana ^b and B. K. Sarojini ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, and ^cDepartment of Chemistry, P. A. College of Engineering, Nadupadavu, Mangalore 574 153, India
^*Correspondence e-mail: hkfun@usm.my

(Received 23 April 2012; accepted 23 April 2012; online 28 April 2012)

In the title compound, C₂₈H₁₈F₄O₂, the central benzene ring makes dihedral angles of 44.27 (6), 56.33 (5) and 77.27 (6)° with the two adjacent fluorobenzene rings and terminal difluoro-substituted benzene ring, respectively. The dihedral angle between the fluorobenzene rings is 87.81 (6)°. The methoxy and prop-2-en-1-one groups are essentially coplanar with their attached benzene rings, as indicated by their C—O—C_ar—C_ar [−0.06 (15)°] and C—C—C_ar—C_ar [4.5 (2)°] (ar = aromatic) torsion angles. In the crystal, molecules are linked by C—H⋯F and C—H⋯O hydrogen bonds into sheets lying parallel to the ac plane. The crystal structure also features C—H⋯π interactions.

Related literature

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

Experimental

Crystal data

C₂₈H₁₈F₄O₂
M_r = 462.42
Triclinic, $[P \overline 1]$
a = 8.9624 (5) Å
b = 10.2127 (6) Å
c = 13.3281 (7) Å
α = 67.780 (1)°
β = 86.776 (1)°
γ = 85.293 (1)°
V = 1125.10 (11) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 100 K
0.25 × 0.20 × 0.11 mm

Data collection

Bruker APEX Duo CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.974, T_max = 0.989
28220 measured reflections
8063 independent reflections
6097 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.144
S = 1.02
8063 reflections
308 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C7–C12 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯F3ⁱ	0.93	2.46	3.3655 (18)	164
C8—H8A⋯F4ⁱⁱ	0.93	2.45	3.3726 (13)	170
C24—H24A⋯O2ⁱⁱⁱ	0.93	2.57	3.4371 (14)	155
C20—H20A⋯Cg1^iv	0.93	2.83	3.5082 (14)	130
C27—H27A⋯Cg2^v	0.93	2.68	3.4068 (12)	136
C28—H28B⋯Cg2^vi	0.96	2.90	3.7990 (15)	157
Symmetry codes: (i) x, y, z-1; (ii) -x+1, -y+2, -z; (iii) x+1, y, z; (iv) -x+1, -y+1, -z; (v) -x, -y+2, -z; (vi) -x, -y+1, -z.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681201820X/hb6753sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681201820X/hb6753Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681201820X/hb6753Isup3.cml

checkCIF report

Comment top

In continuation of our work on synthesis of terphenyl chalcones (Fun et al., 2011), the title compound is prepared and its crystal structure is reported. The starting material of the title compound was prepared from 4,4'-difluoro chalcone by several steps (Fun et al., 2012).

In the title compound (Fig. 1), the central benzene ring (C7–C12) makes dihedral angles of 44.27 (6), 56.33 (5) and 77.27 (6)° with the two adjacent fluoro-substituted benzene rings (C1–C6 & C22–C27) and terminal difluoro-substituted benzene ring (C16–C21), respectively. The dihedral angle between the fluoro-substituted benzene rings is 87.81 (6)°. The methoxy (O1/C28) and prop-2-en-1-one (O2/C13–C15) groups are essentially coplanar with C7–C12 and C16–C21 rings, respectively as indicated by their torsion angles C28—O1—C11—C12 = -0.06 (15)° and C14—C15—C16—C17 = 4.5 (2)°. Bond lengths and angles are comparable to those in related structures (Fun et al., 2011,, 2012).

In the crystal (Fig. 2), molecules are linked by C2—H2A···F3, C8—H8A···F4 and C24—H24A···O2 hydrogen bonds (Table 1) into two dimensional networks parallel to ac plane. The crystal also features C—H···π interactions (Table 1), involving Cg1 and Cg2 which are the centroids of C1—C6 and C7—C12 rings, respectively.

Related literature top

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

Experimental top

To a mixture of

1-(4,4''-difluoro-5'-methoxy-1,1':3',1''-terphenyl-4'-yl)ethanone (0.338 g, 0.001 mol) and 2,6-difluorobenzaldehyde (0.142 g, 0.001 mol) in 30 ml e thanol, 0.5 ml of 10% sodium hydroxide solution was added and stirred at 5–10 °C for 3 h. The precipitate formed was collected by filtration and then purified by recrystallization from ethanol. Colourless blocks were grown from acetone solution by slow evaporation and the yield of the compound was 72% (m.p.: 405 K).

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound with 50% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the title compound. The dashed lines represent the hydrogen bonds.

(2E)- 1-(4,4''-Difluoro-5'-methoxy-1,1':3',1''-terphenyl-4'-yl)-3- (2,6-difluorophenyl)prop-2-en-1-one top

Crystal data top

C₂₈H₁₈F₄O₂	Z = 2
M_r = 462.42	F(000) = 476
Triclinic, P1	D_x = 1.365 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.9624 (5) Å	Cell parameters from 7563 reflections
b = 10.2127 (6) Å	θ = 2.3–32.4°
c = 13.3281 (7) Å	µ = 0.11 mm⁻¹
α = 67.780 (1)°	T = 100 K
β = 86.776 (1)°	Block, colourless
γ = 85.293 (1)°	0.25 × 0.20 × 0.11 mm
V = 1125.10 (11) Å³

Data collection top

Bruker APEX Duo CCD diffractometer	8063 independent reflections
Radiation source: fine-focus sealed tube	6097 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
ϕ and ω scans	θ_max = 32.5°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→13
T_min = 0.974, T_max = 0.989	k = −15→14
28220 measured reflections	l = −20→18

Refinement top

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.144	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0774P)² + 0.2553P] where P = (F_o² + 2F_c²)/3
8063 reflections	(Δ/σ)_max < 0.001
308 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₂₈H₁₈F₄O₂	γ = 85.293 (1)°
M_r = 462.42	V = 1125.10 (11) Å³
Triclinic, P1	Z = 2
a = 8.9624 (5) Å	Mo Kα radiation
b = 10.2127 (6) Å	µ = 0.11 mm⁻¹
c = 13.3281 (7) Å	T = 100 K
α = 67.780 (1)°	0.25 × 0.20 × 0.11 mm
β = 86.776 (1)°

Data collection top

Bruker APEX Duo CCD diffractometer	8063 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	6097 reflections with I > 2σ(I)
T_min = 0.974, T_max = 0.989	R_int = 0.035
28220 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.144	H-atom parameters constrained
S = 1.02	Δρ_max = 0.40 e Å⁻³
8063 reflections	Δρ_min = −0.35 e Å⁻³
308 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
F1	0.17366 (10)	0.87097 (10)	−0.57879 (6)	0.03431 (19)
F2	0.40523 (9)	0.37977 (9)	0.20352 (6)	0.03302 (19)
F3	0.15771 (9)	0.45771 (9)	0.49909 (6)	0.03172 (19)
F4	0.54429 (8)	0.99409 (9)	0.24888 (6)	0.02763 (17)
O1	−0.18938 (9)	0.62125 (9)	0.08627 (7)	0.02127 (17)
O2	−0.12638 (9)	0.79463 (9)	0.21502 (7)	0.02271 (17)
C1	0.09479 (14)	0.69493 (13)	−0.29224 (10)	0.0227 (2)
H1A	0.0711	0.6060	−0.2430	0.027*
C2	0.11646 (14)	0.71665 (14)	−0.40139 (10)	0.0261 (2)
H2A	0.1074	0.6437	−0.4259	0.031*
C3	0.15174 (13)	0.84918 (14)	−0.47200 (9)	0.0240 (2)
C4	0.16684 (13)	0.96077 (13)	−0.43948 (9)	0.0221 (2)
H4A	0.1912	1.0490	−0.4895	0.027*
C5	0.14462 (12)	0.93777 (12)	−0.32982 (9)	0.0187 (2)
H5A	0.1542	1.0113	−0.3061	0.022*
C6	0.10798 (12)	0.80452 (11)	−0.25527 (8)	0.01738 (19)
C7	0.08139 (12)	0.78028 (11)	−0.13880 (9)	0.01654 (19)
C8	0.17578 (12)	0.83272 (11)	−0.08525 (8)	0.01669 (19)
H8A	0.2581	0.8809	−0.1224	0.020*
C9	0.14842 (11)	0.81386 (11)	0.02356 (8)	0.01554 (18)
C10	0.02237 (11)	0.74476 (11)	0.07864 (8)	0.01598 (19)
C11	−0.07150 (11)	0.68975 (11)	0.02521 (9)	0.01676 (19)
C12	−0.04140 (12)	0.70569 (11)	−0.08225 (9)	0.01702 (19)
H12A	−0.1025	0.6670	−0.1165	0.020*
C13	−0.01691 (11)	0.72807 (11)	0.19450 (9)	0.01693 (19)
C14	0.07608 (12)	0.62893 (12)	0.28288 (9)	0.0188 (2)
H14A	0.0601	0.6290	0.3524	0.023*
C15	0.18306 (12)	0.53861 (11)	0.26616 (9)	0.0178 (2)
H15A	0.2000	0.5474	0.1945	0.021*
C16	0.27629 (12)	0.42826 (12)	0.34593 (9)	0.0182 (2)
C17	0.26488 (13)	0.38889 (13)	0.45849 (9)	0.0218 (2)
C18	0.35385 (14)	0.28272 (14)	0.53126 (10)	0.0256 (2)
H18A	0.3412	0.2608	0.6054	0.031*
C19	0.46305 (14)	0.20924 (14)	0.49095 (10)	0.0279 (3)
H19A	0.5247	0.1377	0.5386	0.033*
C20	0.48077 (14)	0.24180 (14)	0.38016 (10)	0.0275 (3)
H20A	0.5533	0.1927	0.3528	0.033*
C21	0.38792 (13)	0.34881 (13)	0.31183 (9)	0.0221 (2)
C22	0.25400 (11)	0.86676 (11)	0.07971 (8)	0.01586 (19)
C23	0.40626 (12)	0.82182 (12)	0.08352 (9)	0.0199 (2)
H23A	0.4414	0.7629	0.0474	0.024*
C24	0.50582 (12)	0.86360 (13)	0.14022 (9)	0.0224 (2)
H24A	0.6066	0.8328	0.1435	0.027*
C25	0.44924 (12)	0.95271 (12)	0.19155 (9)	0.0201 (2)
C26	0.30110 (13)	1.00312 (12)	0.18763 (9)	0.0202 (2)
H26A	0.2678	1.0650	0.2217	0.024*
C27	0.20311 (12)	0.95877 (11)	0.13136 (9)	0.0182 (2)
H27A	0.1026	0.9908	0.1281	0.022*
C28	−0.28775 (13)	0.56257 (13)	0.03620 (10)	0.0231 (2)
H28A	−0.3641	0.5157	0.0877	0.035*
H28B	−0.2319	0.4955	0.0117	0.035*
H28C	−0.3334	0.6371	−0.0245	0.035*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0361 (4)	0.0511 (5)	0.0166 (3)	−0.0008 (4)	0.0005 (3)	−0.0142 (3)
F2	0.0317 (4)	0.0454 (5)	0.0188 (3)	0.0145 (3)	−0.0004 (3)	−0.0119 (3)
F3	0.0370 (4)	0.0357 (4)	0.0187 (3)	0.0152 (3)	0.0003 (3)	−0.0097 (3)
F4	0.0223 (3)	0.0393 (4)	0.0230 (3)	−0.0097 (3)	−0.0061 (3)	−0.0114 (3)
O1	0.0178 (4)	0.0265 (4)	0.0193 (4)	−0.0074 (3)	0.0010 (3)	−0.0073 (3)
O2	0.0168 (4)	0.0280 (4)	0.0234 (4)	0.0035 (3)	−0.0005 (3)	−0.0108 (3)
C1	0.0253 (5)	0.0232 (5)	0.0213 (5)	−0.0032 (4)	−0.0009 (4)	−0.0099 (4)
C2	0.0286 (6)	0.0317 (6)	0.0230 (5)	−0.0022 (5)	−0.0014 (4)	−0.0160 (5)
C3	0.0204 (5)	0.0365 (6)	0.0152 (5)	0.0014 (4)	−0.0014 (4)	−0.0105 (4)
C4	0.0188 (5)	0.0264 (5)	0.0177 (5)	0.0002 (4)	−0.0017 (4)	−0.0046 (4)
C5	0.0164 (4)	0.0209 (5)	0.0180 (5)	−0.0001 (4)	−0.0020 (4)	−0.0064 (4)
C6	0.0151 (4)	0.0207 (5)	0.0164 (4)	−0.0002 (3)	−0.0016 (3)	−0.0070 (4)
C7	0.0160 (4)	0.0169 (4)	0.0166 (4)	0.0005 (3)	−0.0018 (3)	−0.0063 (4)
C8	0.0144 (4)	0.0188 (4)	0.0165 (4)	−0.0007 (3)	−0.0003 (3)	−0.0063 (4)
C9	0.0125 (4)	0.0172 (4)	0.0167 (4)	0.0013 (3)	−0.0018 (3)	−0.0063 (4)
C10	0.0141 (4)	0.0173 (4)	0.0156 (4)	0.0011 (3)	−0.0019 (3)	−0.0054 (4)
C11	0.0145 (4)	0.0170 (4)	0.0173 (4)	−0.0007 (3)	−0.0008 (3)	−0.0048 (4)
C12	0.0160 (4)	0.0179 (4)	0.0174 (4)	−0.0012 (3)	−0.0023 (3)	−0.0067 (4)
C13	0.0145 (4)	0.0187 (4)	0.0178 (5)	−0.0014 (3)	−0.0007 (3)	−0.0070 (4)
C14	0.0175 (5)	0.0228 (5)	0.0156 (4)	0.0006 (4)	−0.0010 (4)	−0.0070 (4)
C15	0.0167 (4)	0.0201 (5)	0.0157 (4)	−0.0007 (4)	−0.0011 (3)	−0.0056 (4)
C16	0.0161 (4)	0.0210 (5)	0.0169 (5)	0.0000 (4)	−0.0010 (4)	−0.0067 (4)
C17	0.0215 (5)	0.0239 (5)	0.0191 (5)	0.0035 (4)	−0.0005 (4)	−0.0081 (4)
C18	0.0260 (6)	0.0292 (6)	0.0180 (5)	0.0046 (4)	−0.0031 (4)	−0.0058 (4)
C19	0.0242 (6)	0.0306 (6)	0.0235 (6)	0.0067 (5)	−0.0042 (4)	−0.0053 (5)
C20	0.0220 (5)	0.0328 (6)	0.0239 (6)	0.0095 (5)	−0.0010 (4)	−0.0086 (5)
C21	0.0190 (5)	0.0283 (5)	0.0173 (5)	0.0034 (4)	−0.0003 (4)	−0.0079 (4)
C22	0.0130 (4)	0.0187 (4)	0.0149 (4)	−0.0010 (3)	−0.0015 (3)	−0.0050 (4)
C23	0.0145 (4)	0.0244 (5)	0.0213 (5)	0.0008 (4)	−0.0011 (4)	−0.0094 (4)
C24	0.0130 (4)	0.0305 (6)	0.0222 (5)	−0.0002 (4)	−0.0033 (4)	−0.0082 (4)
C25	0.0180 (5)	0.0254 (5)	0.0158 (4)	−0.0059 (4)	−0.0043 (4)	−0.0050 (4)
C26	0.0206 (5)	0.0220 (5)	0.0192 (5)	−0.0026 (4)	−0.0009 (4)	−0.0087 (4)
C27	0.0147 (4)	0.0203 (5)	0.0194 (5)	0.0008 (3)	−0.0024 (3)	−0.0072 (4)
C28	0.0171 (5)	0.0268 (5)	0.0276 (6)	−0.0058 (4)	−0.0004 (4)	−0.0117 (5)

Geometric parameters (Å, º) top

F1—C3	1.3602 (13)	C13—C14	1.4756 (15)
F2—C21	1.3585 (13)	C14—C15	1.3440 (15)
F3—C17	1.3519 (13)	C14—H14A	0.9300
F4—C25	1.3656 (13)	C15—C16	1.4621 (15)
O1—C11	1.3645 (13)	C15—H15A	0.9300
O1—C28	1.4274 (14)	C16—C17	1.3985 (15)
O2—C13	1.2249 (13)	C16—C21	1.4002 (15)
C1—C2	1.3908 (16)	C17—C18	1.3791 (16)
C1—C6	1.3981 (16)	C18—C19	1.3910 (17)
C1—H1A	0.9300	C18—H18A	0.9300
C2—C3	1.3751 (18)	C19—C20	1.3882 (17)
C2—H2A	0.9300	C19—H19A	0.9300
C3—C4	1.3823 (18)	C20—C21	1.3782 (16)
C4—C5	1.3951 (15)	C20—H20A	0.9300
C4—H4A	0.9300	C22—C27	1.3958 (15)
C5—C6	1.4003 (15)	C22—C23	1.4010 (14)
C5—H5A	0.9300	C23—C24	1.3897 (16)
C6—C7	1.4850 (15)	C23—H23A	0.9300
C7—C8	1.3939 (15)	C24—C25	1.3819 (17)
C7—C12	1.4034 (15)	C24—H24A	0.9300
C8—C9	1.3990 (14)	C25—C26	1.3805 (16)
C8—H8A	0.9300	C26—C27	1.3912 (15)
C9—C10	1.3996 (14)	C26—H26A	0.9300
C9—C22	1.4888 (15)	C27—H27A	0.9300
C10—C11	1.4064 (15)	C28—H28A	0.9600
C10—C13	1.5123 (14)	C28—H28B	0.9600
C11—C12	1.3921 (15)	C28—H28C	0.9600
C12—H12A	0.9300

C11—O1—C28	117.58 (9)	C14—C15—H15A	115.8
C2—C1—C6	121.10 (11)	C16—C15—H15A	115.8
C2—C1—H1A	119.5	C17—C16—C21	113.73 (10)
C6—C1—H1A	119.5	C17—C16—C15	126.22 (10)
C3—C2—C1	118.01 (11)	C21—C16—C15	120.04 (10)
C3—C2—H2A	121.0	F3—C17—C18	117.61 (10)
C1—C2—H2A	121.0	F3—C17—C16	117.92 (10)
F1—C3—C2	118.31 (11)	C18—C17—C16	124.46 (10)
F1—C3—C4	118.56 (11)	C17—C18—C19	118.36 (11)
C2—C3—C4	123.13 (11)	C17—C18—H18A	120.8
C3—C4—C5	118.34 (11)	C19—C18—H18A	120.8
C3—C4—H4A	120.8	C20—C19—C18	120.55 (11)
C5—C4—H4A	120.8	C20—C19—H19A	119.7
C4—C5—C6	120.35 (11)	C18—C19—H19A	119.7
C4—C5—H5A	119.8	C21—C20—C19	118.19 (11)
C6—C5—H5A	119.8	C21—C20—H20A	120.9
C1—C6—C5	119.07 (10)	C19—C20—H20A	120.9
C1—C6—C7	120.38 (10)	F2—C21—C20	117.95 (10)
C5—C6—C7	120.55 (10)	F2—C21—C16	117.34 (10)
C8—C7—C12	119.51 (10)	C20—C21—C16	124.70 (11)
C8—C7—C6	120.74 (9)	C27—C22—C23	118.94 (10)
C12—C7—C6	119.75 (10)	C27—C22—C9	120.92 (9)
C7—C8—C9	120.89 (10)	C23—C22—C9	120.12 (9)
C7—C8—H8A	119.6	C24—C23—C22	121.32 (10)
C9—C8—H8A	119.6	C24—C23—H23A	119.3
C8—C9—C10	119.59 (10)	C22—C23—H23A	119.3
C8—C9—C22	119.71 (9)	C25—C24—C23	117.43 (10)
C10—C9—C22	120.71 (9)	C25—C24—H24A	121.3
C9—C10—C11	119.51 (9)	C23—C24—H24A	121.3
C9—C10—C13	121.81 (9)	F4—C25—C26	117.91 (10)
C11—C10—C13	118.68 (9)	F4—C25—C24	118.65 (10)
O1—C11—C12	124.20 (10)	C26—C25—C24	123.44 (11)
O1—C11—C10	115.25 (9)	C25—C26—C27	118.14 (10)
C12—C11—C10	120.55 (10)	C25—C26—H26A	120.9
C11—C12—C7	119.86 (10)	C27—C26—H26A	120.9
C11—C12—H12A	120.1	C26—C27—C22	120.70 (10)
C7—C12—H12A	120.1	C26—C27—H27A	119.7
O2—C13—C14	120.22 (10)	C22—C27—H27A	119.7
O2—C13—C10	120.30 (9)	O1—C28—H28A	109.5
C14—C13—C10	119.47 (9)	O1—C28—H28B	109.5
C15—C14—C13	122.15 (10)	H28A—C28—H28B	109.5
C15—C14—H14A	118.9	O1—C28—H28C	109.5
C13—C14—H14A	118.9	H28A—C28—H28C	109.5
C14—C15—C16	128.48 (10)	H28B—C28—H28C	109.5

C6—C1—C2—C3	0.19 (18)	C11—C10—C13—C14	109.02 (11)
C1—C2—C3—F1	179.74 (11)	O2—C13—C14—C15	169.89 (11)
C1—C2—C3—C4	0.16 (19)	C10—C13—C14—C15	−8.99 (16)
F1—C3—C4—C5	−179.84 (10)	C13—C14—C15—C16	−175.29 (11)
C2—C3—C4—C5	−0.25 (18)	C14—C15—C16—C17	4.5 (2)
C3—C4—C5—C6	0.00 (16)	C14—C15—C16—C21	−176.78 (12)
C2—C1—C6—C5	−0.43 (17)	C21—C16—C17—F3	−178.53 (11)
C2—C1—C6—C7	178.74 (10)	C15—C16—C17—F3	0.30 (18)
C4—C5—C6—C1	0.33 (16)	C21—C16—C17—C18	0.26 (18)
C4—C5—C6—C7	−178.83 (10)	C15—C16—C17—C18	179.09 (12)
C1—C6—C7—C8	137.19 (11)	F3—C17—C18—C19	178.96 (12)
C5—C6—C7—C8	−43.66 (14)	C16—C17—C18—C19	0.2 (2)
C1—C6—C7—C12	−43.81 (15)	C17—C18—C19—C20	−0.4 (2)
C5—C6—C7—C12	135.34 (11)	C18—C19—C20—C21	0.3 (2)
C12—C7—C8—C9	−0.99 (15)	C19—C20—C21—F2	−179.68 (12)
C6—C7—C8—C9	178.01 (9)	C19—C20—C21—C16	0.2 (2)
C7—C8—C9—C10	−1.73 (15)	C17—C16—C21—F2	179.42 (11)
C7—C8—C9—C22	177.95 (9)	C15—C16—C21—F2	0.51 (17)
C8—C9—C10—C11	2.77 (15)	C17—C16—C21—C20	−0.45 (18)
C22—C9—C10—C11	−176.91 (9)	C15—C16—C21—C20	−179.36 (12)
C8—C9—C10—C13	−176.84 (9)	C8—C9—C22—C27	125.20 (11)
C22—C9—C10—C13	3.48 (15)	C10—C9—C22—C27	−55.12 (14)
C28—O1—C11—C12	−0.06 (15)	C8—C9—C22—C23	−56.29 (14)
C28—O1—C11—C10	−179.63 (9)	C10—C9—C22—C23	123.38 (11)
C9—C10—C11—O1	178.46 (9)	C27—C22—C23—C24	1.97 (16)
C13—C10—C11—O1	−1.92 (14)	C9—C22—C23—C24	−176.57 (10)
C9—C10—C11—C12	−1.12 (15)	C22—C23—C24—C25	−0.82 (17)
C13—C10—C11—C12	178.50 (9)	C23—C24—C25—F4	179.25 (10)
O1—C11—C12—C7	178.86 (10)	C23—C24—C25—C26	−1.08 (18)
C10—C11—C12—C7	−1.60 (15)	F4—C25—C26—C27	−178.59 (10)
C8—C7—C12—C11	2.64 (15)	C24—C25—C26—C27	1.74 (17)
C6—C7—C12—C11	−176.37 (9)	C25—C26—C27—C22	−0.51 (16)
C9—C10—C13—O2	109.75 (12)	C23—C22—C27—C26	−1.27 (16)
C11—C10—C13—O2	−69.86 (14)	C9—C22—C27—C26	177.25 (10)
C9—C10—C13—C14	−71.37 (14)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C7–C12 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···F3ⁱ	0.93	2.46	3.3655 (18)	164
C8—H8A···F4ⁱⁱ	0.93	2.45	3.3726 (13)	170
C24—H24A···O2ⁱⁱⁱ	0.93	2.57	3.4371 (14)	155
C20—H20A···Cg1^iv	0.93	2.83	3.5082 (14)	130
C27—H27A···Cg2^v	0.93	2.68	3.4068 (12)	136
C28—H28B···Cg2^vi	0.96	2.90	3.7990 (15)	157

Symmetry codes: (i) x, y, z−1; (ii) −x+1, −y+2, −z; (iii) x+1, y, z; (iv) −x+1, −y+1, −z; (v) −x, −y+2, −z; (vi) −x, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₂₈H₁₈F₄O₂
M_r	462.42
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	8.9624 (5), 10.2127 (6), 13.3281 (7)
α, β, γ (°)	67.780 (1), 86.776 (1), 85.293 (1)
V (Å³)	1125.10 (11)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.25 × 0.20 × 0.11

Data collection
Diffractometer	Bruker APEX Duo CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.974, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	28220, 8063, 6097
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.757

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.144, 1.02
No. of reflections	8063
No. of parameters	308
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.35

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C7–C12 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···F3ⁱ	0.93	2.46	3.3655 (18)	164
C8—H8A···F4ⁱⁱ	0.93	2.45	3.3726 (13)	170
C24—H24A···O2ⁱⁱⁱ	0.93	2.57	3.4371 (14)	155
C20—H20A···Cg1^iv	0.93	2.83	3.5082 (14)	130
C27—H27A···Cg2^v	0.93	2.68	3.4068 (12)	136
C28—H28B···Cg2^vi	0.96	2.90	3.7990 (15)	157

Symmetry codes: (i) x, y, z−1; (ii) −x+1, −y+2, −z; (iii) x+1, y, z; (iv) −x+1, −y+1, −z; (v) −x, −y+2, −z; (vi) −x, −y+1, −z.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and TSC thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). TSC also thanks the Malaysian Government and USM for the award of a research fellowship. BN thanks the UGC for financial assistance through the SAP and BSR one-time grant for the purchase of chemicals. SS thanks Mangalore University for the research facilities.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Fun, H.-K., Hemamalini, M., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2011). Acta Cryst. E67, o3327–o3328. Web of Science CSD CrossRef IUCr Journals Google Scholar
Fun, H.-K., Hemamalini, M., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2012). Acta Cryst. E68, o163. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 5| May 2012| Pages o1560-o1561

doi:10.1107/S160053681201820X

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(2E)-1-(4,4′′-Di­fluoro-5′-meth­­oxy-1,1′:3′,1′′-terphenyl-4′-yl)-3-(2,6-di­fluoro­phen­yl)prop-2-en-1-one

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

(2E)-1-(4,4′′-Difluoro-5′-methoxy-1,1′:3′,1′′-terphenyl-4′-yl)-3-(2,6-difluorophenyl)prop-2-en-1-one