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

Betz, R.; Gerber, T.; Hosten, E.; Samshuddin, S.; Narayana, B.; Sarojini, B.K.

doi:10.1107/S1600536811042279

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Pages o2996-o2997

doi:10.1107/S1600536811042279

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

Richard Betz,^a ^* Thomas Gerber,^a Eric Hosten,^a S. Samshuddin,^b Badiadka Narayana ^b and Balladka K. Sarojini ^c

^aNelson Mandela Metropolitan University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth 6031, South Africa, ^bMangalore University, Department of Studies in Chemistry, Mangalagangotri 574 199, India, and ^cP.A. College of Engineering, Department of Chemistry, Nadupadavu, Mangalore 574 199, India
^*Correspondence e-mail: richard.betz@webmail.co.za

(Received 10 October 2011; accepted 13 October 2011; online 22 October 2011)

In the title compound, C₂₈H₁₉F₃O₂, the C=C double bond has an E configuration. In the crystal, C—H⋯F contacts link the molecules into chains along [111]. The shortest centroid–centroid distance between two π systems is 3.8087 (8) Å and is apparent between the para-fluorophenyl group attached to the Michael system 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 work on the synthesis and strcutures of different chalcone derivatives, see: Samshuddin et al. (2011a ,b ); Fun et al. (2010a ,b ); Jasinski et al. (2010a ,b ); Baktir et al. (2011a ,b ). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ); Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₈H₁₉F₃O₂
M_r = 444.43
Monoclinic, P 2₁ /c
a = 22.5742 (5) Å
b = 6.8101 (1) Å
c = 13.8475 (3) Å
β = 98.405 (1)°
V = 2105.95 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 200 K
0.56 × 0.26 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer
35196 measured reflections
5218 independent reflections
4087 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.102
S = 1.04
5218 reflections
299 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C25—H25⋯F1ⁱ	0.95	2.55	3.2276 (15)	129
C43—H43⋯F2ⁱⁱ	0.95	2.53	3.4449 (16)	161
Symmetry codes: (i) -x, -y+2, -z+1; (ii) -x+1, -y+1, -z.

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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811042279/zl2413sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811042279/zl2413Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811042279/zl2413Isup3.cdx

Supporting information file. DOI: 10.1107/S1600536811042279/zl2413Isup4.cml

checkCIF report

Comment top

Chalcones constitute an important family of substances belonging to flavonoids, a large group of natural and synthetic products with interesting physicochemical properties, biological activity and structural characteristics. They have been reported to possess many interesting pharmacological activities (Dhar, 1981) including anti-inflammatory, antimicrobial, antifungal, antioxidant, cytotoxic, antitumor and anticancer activities (Dimmock et al., 1999; Satyanarayana et al., 2004). In recent years, it has been reported that some terphenyls exhibit considerable biological activities (e.g. being potent anticoagulants, immunosuppressants, antithrombotics, neuroprotectives, specific 5-lipoxygenase inhibitors) and showing cytotoxic activities (Liu, 2006). In view of the pharmacological importance of terphenyls and chalcones, and in continuation of our work on synthesis of various derivatives of 4,4'-difluoro chalcone (Samshuddin et al., 2011a/b, Fun et al., 2010a/b, Jasinski et al., 2010a/b, Baktir et al., 2011a/b), the molecular and crystal structure of the title compound is reported.

The C=C double of the Michael system is (E)-configured. The least-squares planes defined by the carbon atoms of the para-fluoro phenyl rings of the terphenyl moiety and its central phenyl ring enclose angles of 40.37 (6)° and 44.04 (6)°, respectively (Fig. 1).

In the crystal, two different C–H···F contacts whose range falls by more than 0.1 Å below the sum of van-der-Waals radii of the atoms participating are observed. The first contact is apparent between one of the fluorine atoms on the terphenyl skeleton and a hydrogen atom on the terminal aromatic substituent on the Michael system's substituent. The second one is supported by the second fluorine atom on the terphenyl skeleton and a hydrogen atom on its symmetry-generated equivalent. Both contacts connect the molecules in such a way that cyclic patterns with local inversion symmetry are generated. In terms of graph-set analysis (Etter et al., 1990; Bernstein et al., 1995), the descriptor for the C–H···F contacts is R²₂(8)R²₂(28) on the unitary level. In total, the molecules are connected to infinite chains along [1 1 1]. Metrical parameters as well as information about the symmetry of these contacts is summarized in Table 1. The shortest intercentroid distance between two π systems was found at 3.8087 (8) Å and is apparent between the para-fluoro phenyl moiety attached to the Michael system and its symmetry-generated equivalent. (Fig. 2).

The packing of the title compound in the crystal is shown in Figure 3.

Related literature top

For the pharmacological importance of terphenyls, see: Liu (2006) and of chalcones, see: Dhar (1981); Dimmock et al. (1999); Satyanarayana et al. (2004). For work on the synthesis of different chalcone derivatives, see: Samshuddin et al. (2011a,b); Fun et al. (2010a,b); Jasinski et al. (2010a,b); Baktir et al. (2011a,b). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990); Bernstein et al. (1995).

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 p-fluorobenzaldehyde (0.124 g, 0.001 mol) in 30 ml e thanol, 1 ml of 10% sodium hydroxide solution was added and stirred at 278–283 K for 3 h. The precipitate formed was collected by filtration and purified by recrystallization from ethanol (yield: 83%). Single crystals suitable for the X-ray diffraction study were grown from a 1:1 (v:v) mixture of DMF and ethanol by slow evaporation at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); 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 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labels and anisotropic displacement ellipsoids (drawn at 50% probability level).
	Fig. 2. Intermolecular contacts, viewed along [0 1 0]. Symmetry operators: ⁱ -x, -y + 2, -z + 1; ⁱⁱ -x + 1, -y + 1, -z.
	Fig. 3. Molecular packing of the title compound, viewed along [0 1 0] (anisotropic displacement ellipsoids drawn at 50% probability level).

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

Crystal data top

C₂₈H₁₉F₃O₂	F(000) = 920
M_r = 444.43	D_x = 1.402 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 549 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 22.5742 (5) Å	Cell parameters from 9830 reflections
b = 6.8101 (1) Å	θ = 3.0–28.3°
c = 13.8475 (3) Å	µ = 0.11 mm⁻¹
β = 98.405 (1)°	T = 200 K
V = 2105.95 (7) Å³	Block, yellow
Z = 4	0.56 × 0.26 × 0.18 mm

Data collection top

Bruker APEXII CCD diffractometer	4087 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.032
Graphite monochromator	θ_max = 28.3°, θ_min = 1.8°
ϕ and ω scans	h = −30→30
35196 measured reflections	k = −9→8
5218 independent reflections	l = −18→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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.102	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0462P)² + 0.5814P] where P = (F_o² + 2F_c²)/3
5218 reflections	(Δ/σ)_max < 0.001
299 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₂₈H₁₉F₃O₂	V = 2105.95 (7) Å³
M_r = 444.43	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 22.5742 (5) Å	µ = 0.11 mm⁻¹
b = 6.8101 (1) Å	T = 200 K
c = 13.8475 (3) Å	0.56 × 0.26 × 0.18 mm
β = 98.405 (1)°

Data collection top

Bruker APEXII CCD diffractometer	4087 reflections with I > 2σ(I)
35196 measured reflections	R_int = 0.032
5218 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.102	H-atom parameters constrained
S = 1.04	Δρ_max = 0.30 e Å⁻³
5218 reflections	Δρ_min = −0.19 e Å⁻³
299 parameters

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

	x	y	z	U_iso*/U_eq
F1	−0.04953 (4)	0.88945 (14)	0.40789 (7)	0.0567 (3)
F2	0.37032 (4)	0.00783 (12)	0.22814 (6)	0.0486 (2)
F3	0.53866 (4)	1.35725 (17)	−0.11810 (8)	0.0755 (3)
O1	0.25624 (4)	0.57595 (14)	−0.06967 (7)	0.0445 (2)
O2	0.18161 (4)	1.02710 (14)	−0.05061 (7)	0.0422 (2)
C1	0.25957 (5)	0.72789 (19)	−0.02279 (8)	0.0317 (3)
C2	0.30451 (6)	0.88085 (19)	−0.03214 (9)	0.0343 (3)
H2	0.3015	1.0037	−0.0007	0.041*
C3	0.34907 (5)	0.85151 (19)	−0.08335 (9)	0.0342 (3)
H3	0.3493	0.7298	−0.1168	0.041*
C4	0.15353 (7)	1.2144 (2)	−0.06059 (10)	0.0455 (3)
H4A	0.1662	1.2924	−0.0017	0.068*
H4B	0.1100	1.1977	−0.0695	0.068*
H4C	0.1651	1.2821	−0.1175	0.068*
C11	0.21736 (5)	0.76519 (17)	0.05006 (8)	0.0291 (2)
C12	0.17663 (5)	0.92003 (18)	0.03161 (9)	0.0313 (3)
C13	0.13322 (5)	0.95422 (18)	0.09070 (9)	0.0310 (3)
H13	0.1050	1.0572	0.0756	0.037*
C14	0.13129 (5)	0.83612 (17)	0.17253 (8)	0.0285 (2)
C15	0.17348 (5)	0.68782 (17)	0.19389 (8)	0.0287 (2)
H15	0.1733	0.6120	0.2514	0.034*
C16	0.21618 (5)	0.64726 (17)	0.13284 (8)	0.0279 (2)
C21	0.08371 (5)	0.86298 (16)	0.23502 (9)	0.0289 (2)
C22	0.02421 (5)	0.89054 (18)	0.19403 (9)	0.0331 (3)
H22	0.0143	0.9020	0.1252	0.040*
C23	−0.02064 (6)	0.90140 (18)	0.25208 (10)	0.0375 (3)
H23	−0.0612	0.9206	0.2240	0.045*
C24	−0.00510 (6)	0.88379 (18)	0.35085 (10)	0.0384 (3)
C25	0.05286 (6)	0.8598 (2)	0.39518 (10)	0.0398 (3)
H25	0.0622	0.8508	0.4642	0.048*
C26	0.09725 (6)	0.84925 (18)	0.33614 (9)	0.0345 (3)
H26	0.1377	0.8323	0.3652	0.041*
C31	0.25833 (5)	0.48112 (17)	0.15868 (8)	0.0274 (2)
C32	0.23728 (5)	0.30657 (18)	0.19374 (9)	0.0312 (3)
H32	0.1962	0.2967	0.2010	0.037*
C33	0.27442 (6)	0.14721 (18)	0.21833 (9)	0.0343 (3)
H33	0.2596	0.0294	0.2426	0.041*
C34	0.33354 (6)	0.16525 (18)	0.20640 (9)	0.0333 (3)
C35	0.35695 (5)	0.3347 (2)	0.17383 (9)	0.0352 (3)
H35	0.3982	0.3430	0.1673	0.042*
C36	0.31926 (5)	0.49307 (18)	0.15071 (9)	0.0322 (3)
H36	0.3350	0.6119	0.1290	0.039*
C41	0.39775 (5)	0.9881 (2)	−0.09336 (9)	0.0340 (3)
C42	0.44727 (6)	0.9221 (2)	−0.13332 (10)	0.0425 (3)
H42	0.4484	0.7899	−0.1550	0.051*
C43	0.49492 (6)	1.0455 (3)	−0.14204 (11)	0.0504 (4)
H43	0.5288	0.9998	−0.1690	0.060*
C44	0.49179 (6)	1.2347 (3)	−0.11076 (11)	0.0498 (4)
C45	0.44382 (7)	1.3083 (2)	−0.07209 (10)	0.0473 (3)
H45	0.4431	1.4414	−0.0516	0.057*
C46	0.39656 (6)	1.1840 (2)	−0.06367 (9)	0.0394 (3)
H46	0.3628	1.2322	−0.0374	0.047*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0539 (5)	0.0573 (6)	0.0682 (6)	−0.0014 (4)	0.0407 (4)	−0.0098 (4)
F2	0.0448 (5)	0.0415 (5)	0.0603 (5)	0.0126 (4)	0.0102 (4)	0.0063 (4)
F3	0.0552 (6)	0.0899 (8)	0.0845 (7)	−0.0380 (5)	0.0209 (5)	0.0072 (6)
O1	0.0498 (6)	0.0425 (5)	0.0458 (5)	−0.0121 (4)	0.0220 (4)	−0.0141 (4)
O2	0.0514 (6)	0.0377 (5)	0.0416 (5)	0.0052 (4)	0.0203 (4)	0.0118 (4)
C1	0.0316 (6)	0.0353 (6)	0.0295 (6)	−0.0033 (5)	0.0092 (5)	−0.0003 (5)
C2	0.0372 (6)	0.0345 (6)	0.0334 (6)	−0.0059 (5)	0.0125 (5)	−0.0022 (5)
C3	0.0348 (6)	0.0366 (7)	0.0327 (6)	−0.0028 (5)	0.0096 (5)	0.0012 (5)
C4	0.0596 (9)	0.0370 (7)	0.0394 (7)	0.0012 (6)	0.0055 (6)	0.0090 (6)
C11	0.0291 (6)	0.0289 (6)	0.0308 (6)	−0.0061 (4)	0.0092 (4)	−0.0028 (5)
C12	0.0347 (6)	0.0288 (6)	0.0317 (6)	−0.0053 (5)	0.0093 (5)	0.0011 (5)
C13	0.0309 (6)	0.0272 (6)	0.0359 (6)	−0.0006 (5)	0.0080 (5)	−0.0006 (5)
C14	0.0283 (6)	0.0271 (6)	0.0313 (6)	−0.0057 (4)	0.0085 (4)	−0.0040 (4)
C15	0.0298 (6)	0.0285 (6)	0.0295 (5)	−0.0044 (5)	0.0094 (4)	−0.0002 (5)
C16	0.0275 (5)	0.0268 (6)	0.0305 (6)	−0.0056 (4)	0.0075 (4)	−0.0033 (4)
C21	0.0305 (6)	0.0228 (5)	0.0351 (6)	−0.0024 (4)	0.0113 (5)	−0.0027 (5)
C22	0.0349 (6)	0.0289 (6)	0.0367 (6)	0.0008 (5)	0.0090 (5)	−0.0008 (5)
C23	0.0310 (6)	0.0302 (6)	0.0534 (8)	0.0008 (5)	0.0129 (6)	−0.0041 (6)
C24	0.0425 (7)	0.0290 (6)	0.0498 (8)	−0.0018 (5)	0.0273 (6)	−0.0070 (5)
C25	0.0493 (8)	0.0382 (7)	0.0348 (6)	0.0004 (6)	0.0163 (6)	−0.0049 (5)
C26	0.0351 (6)	0.0342 (6)	0.0355 (6)	−0.0002 (5)	0.0090 (5)	−0.0046 (5)
C31	0.0286 (6)	0.0287 (6)	0.0260 (5)	−0.0036 (4)	0.0082 (4)	−0.0045 (4)
C32	0.0295 (6)	0.0325 (6)	0.0335 (6)	−0.0035 (5)	0.0109 (5)	−0.0020 (5)
C33	0.0387 (7)	0.0291 (6)	0.0365 (6)	−0.0036 (5)	0.0102 (5)	0.0008 (5)
C34	0.0357 (6)	0.0325 (6)	0.0318 (6)	0.0048 (5)	0.0055 (5)	−0.0028 (5)
C35	0.0270 (6)	0.0419 (7)	0.0376 (6)	−0.0010 (5)	0.0083 (5)	−0.0023 (5)
C36	0.0300 (6)	0.0329 (6)	0.0349 (6)	−0.0057 (5)	0.0090 (5)	−0.0005 (5)
C41	0.0303 (6)	0.0427 (7)	0.0301 (6)	−0.0032 (5)	0.0081 (5)	0.0049 (5)
C42	0.0388 (7)	0.0474 (8)	0.0442 (7)	0.0004 (6)	0.0156 (6)	0.0041 (6)
C43	0.0335 (7)	0.0685 (10)	0.0521 (8)	−0.0030 (7)	0.0164 (6)	0.0089 (8)
C44	0.0392 (7)	0.0645 (10)	0.0459 (8)	−0.0186 (7)	0.0070 (6)	0.0121 (7)
C45	0.0503 (8)	0.0474 (8)	0.0445 (8)	−0.0137 (7)	0.0075 (6)	0.0031 (6)
C46	0.0383 (7)	0.0447 (7)	0.0367 (7)	−0.0048 (6)	0.0106 (5)	0.0014 (6)

Geometric parameters (Å, º) top

F1—C24	1.3648 (14)	C22—H22	0.9500
F2—C34	1.3624 (14)	C23—C24	1.367 (2)
F3—C44	1.3628 (16)	C23—H23	0.9500
O1—C1	1.2180 (15)	C24—C25	1.371 (2)
O2—C12	1.3704 (14)	C25—C26	1.3847 (17)
O2—C4	1.4218 (17)	C25—H25	0.9500
C1—C2	1.4729 (17)	C26—H26	0.9500
C1—C11	1.5070 (16)	C31—C32	1.3936 (16)
C2—C3	1.3278 (17)	C31—C36	1.3981 (16)
C2—H2	0.9500	C32—C33	1.3832 (17)
C3—C41	1.4617 (17)	C32—H32	0.9500
C3—H3	0.9500	C33—C34	1.3741 (18)
C4—H4A	0.9800	C33—H33	0.9500
C4—H4B	0.9800	C34—C35	1.3728 (18)
C4—H4C	0.9800	C35—C36	1.3818 (18)
C11—C12	1.3979 (17)	C35—H35	0.9500
C11—C16	1.4030 (16)	C36—H36	0.9500
C12—C13	1.3849 (17)	C41—C42	1.3925 (18)
C13—C14	1.3954 (17)	C41—C46	1.3974 (19)
C13—H13	0.9500	C42—C43	1.384 (2)
C14—C15	1.3900 (16)	C42—H42	0.9500
C14—C21	1.4859 (15)	C43—C44	1.365 (2)
C15—C16	1.3995 (16)	C43—H43	0.9500
C15—H15	0.9500	C44—C45	1.371 (2)
C16—C31	1.4880 (16)	C45—C46	1.3802 (19)
C21—C26	1.3920 (17)	C45—H45	0.9500
C21—C22	1.3923 (17)	C46—H46	0.9500
C22—C23	1.3836 (18)

C12—O2—C4	117.93 (10)	F1—C24—C25	118.55 (12)
O1—C1—C2	122.93 (11)	C23—C24—C25	123.16 (12)
O1—C1—C11	120.28 (11)	C24—C25—C26	117.86 (12)
C2—C1—C11	116.78 (10)	C24—C25—H25	121.1
C3—C2—C1	121.72 (12)	C26—C25—H25	121.1
C3—C2—H2	119.1	C25—C26—C21	121.26 (12)
C1—C2—H2	119.1	C25—C26—H26	119.4
C2—C3—C41	126.41 (12)	C21—C26—H26	119.4
C2—C3—H3	116.8	C32—C31—C36	117.82 (11)
C41—C3—H3	116.8	C32—C31—C16	119.58 (10)
O2—C4—H4A	109.5	C36—C31—C16	122.59 (10)
O2—C4—H4B	109.5	C33—C32—C31	121.98 (11)
H4A—C4—H4B	109.5	C33—C32—H32	119.0
O2—C4—H4C	109.5	C31—C32—H32	119.0
H4A—C4—H4C	109.5	C34—C33—C32	117.69 (11)
H4B—C4—H4C	109.5	C34—C33—H33	121.2
C12—C11—C16	119.38 (10)	C32—C33—H33	121.2
C12—C11—C1	117.91 (10)	F2—C34—C35	118.87 (11)
C16—C11—C1	122.67 (11)	F2—C34—C33	118.31 (11)
O2—C12—C13	123.54 (11)	C35—C34—C33	122.81 (12)
O2—C12—C11	114.93 (10)	C34—C35—C36	118.60 (11)
C13—C12—C11	121.48 (11)	C34—C35—H35	120.7
C12—C13—C14	119.45 (11)	C36—C35—H35	120.7
C12—C13—H13	120.3	C35—C36—C31	121.05 (11)
C14—C13—H13	120.3	C35—C36—H36	119.5
C15—C14—C13	119.33 (10)	C31—C36—H36	119.5
C15—C14—C21	119.78 (10)	C42—C41—C46	118.44 (12)
C13—C14—C21	120.87 (11)	C42—C41—C3	119.38 (12)
C14—C15—C16	121.73 (11)	C46—C41—C3	122.19 (12)
C14—C15—H15	119.1	C43—C42—C41	121.19 (14)
C16—C15—H15	119.1	C43—C42—H42	119.4
C15—C16—C11	118.53 (11)	C41—C42—H42	119.4
C15—C16—C31	118.53 (10)	C44—C43—C42	117.95 (14)
C11—C16—C31	122.95 (10)	C44—C43—H43	121.0
C26—C21—C22	118.43 (11)	C42—C43—H43	121.0
C26—C21—C14	120.42 (11)	F3—C44—C43	118.54 (14)
C22—C21—C14	121.03 (11)	F3—C44—C45	118.12 (15)
C23—C22—C21	120.96 (12)	C43—C44—C45	123.35 (13)
C23—C22—H22	119.5	C44—C45—C46	118.22 (15)
C21—C22—H22	119.5	C44—C45—H45	120.9
C24—C23—C22	118.31 (12)	C46—C45—H45	120.9
C24—C23—H23	120.8	C45—C46—C41	120.84 (13)
C22—C23—H23	120.8	C45—C46—H46	119.6
F1—C24—C23	118.29 (12)	C41—C46—H46	119.6

O1—C1—C2—C3	−8.7 (2)	C22—C23—C24—C25	1.34 (19)
C11—C1—C2—C3	170.25 (12)	F1—C24—C25—C26	178.35 (11)
C1—C2—C3—C41	−176.55 (12)	C23—C24—C25—C26	−1.3 (2)
O1—C1—C11—C12	−114.77 (14)	C24—C25—C26—C21	0.17 (19)
C2—C1—C11—C12	66.28 (15)	C22—C21—C26—C25	0.88 (18)
O1—C1—C11—C16	62.99 (16)	C14—C21—C26—C25	−175.32 (11)
C2—C1—C11—C16	−115.96 (13)	C15—C16—C31—C32	40.84 (15)
C4—O2—C12—C13	19.08 (18)	C11—C16—C31—C32	−139.22 (12)
C4—O2—C12—C11	−163.68 (11)	C15—C16—C31—C36	−138.15 (12)
C16—C11—C12—O2	179.64 (10)	C11—C16—C31—C36	41.80 (17)
C1—C11—C12—O2	−2.53 (15)	C36—C31—C32—C33	−1.33 (17)
C16—C11—C12—C13	−3.06 (17)	C16—C31—C32—C33	179.63 (11)
C1—C11—C12—C13	174.78 (11)	C31—C32—C33—C34	−0.47 (18)
O2—C12—C13—C14	179.37 (11)	C32—C33—C34—F2	−178.47 (11)
C11—C12—C13—C14	2.30 (18)	C32—C33—C34—C35	1.67 (19)
C12—C13—C14—C15	0.79 (17)	F2—C34—C35—C36	179.18 (11)
C12—C13—C14—C21	−177.28 (11)	C33—C34—C35—C36	−0.96 (19)
C13—C14—C15—C16	−3.16 (17)	C34—C35—C36—C31	−0.97 (18)
C21—C14—C15—C16	174.93 (10)	C32—C31—C36—C35	2.07 (17)
C14—C15—C16—C11	2.39 (17)	C16—C31—C36—C35	−178.93 (11)
C14—C15—C16—C31	−177.66 (10)	C2—C3—C41—C42	167.43 (13)
C12—C11—C16—C15	0.71 (16)	C2—C3—C41—C46	−12.3 (2)
C1—C11—C16—C15	−177.02 (10)	C46—C41—C42—C43	1.2 (2)
C12—C11—C16—C31	−179.24 (10)	C3—C41—C42—C43	−178.53 (13)
C1—C11—C16—C31	3.03 (17)	C41—C42—C43—C44	−0.4 (2)
C15—C14—C21—C26	41.88 (16)	C42—C43—C44—F3	179.40 (13)
C13—C14—C21—C26	−140.05 (12)	C42—C43—C44—C45	−0.5 (2)
C15—C14—C21—C22	−134.22 (12)	F3—C44—C45—C46	−179.36 (13)
C13—C14—C21—C22	43.84 (16)	C43—C44—C45—C46	0.6 (2)
C26—C21—C22—C23	−0.87 (18)	C44—C45—C46—C41	0.3 (2)
C14—C21—C22—C23	175.31 (11)	C42—C41—C46—C45	−1.16 (19)
C21—C22—C23—C24	−0.20 (18)	C3—C41—C46—C45	178.57 (12)
C22—C23—C24—F1	−178.34 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C25—H25···F1ⁱ	0.95	2.55	3.2276 (15)	129
C43—H43···F2ⁱⁱ	0.95	2.53	3.4449 (16)	161

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

Experimental details

Crystal data
Chemical formula	C₂₈H₁₉F₃O₂
M_r	444.43
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	200
a, b, c (Å)	22.5742 (5), 6.8101 (1), 13.8475 (3)
β (°)	98.405 (1)
V (Å³)	2105.95 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.56 × 0.26 × 0.18

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	35196, 5218, 4087
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.102, 1.04
No. of reflections	5218
No. of parameters	299
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.19

Computer programs: APEX2 (Bruker, 2010), SAINT (Bruker, 2010), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C25—H25···F1ⁱ	0.95	2.55	3.2276 (15)	128.5
C43—H43···F2ⁱⁱ	0.95	2.53	3.4449 (16)	161.3

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

Acknowledgements

BN thanks the UGC for financial assistance through the SAP and BSR for one-time grants for the purchase of chemicals. SS thanks Mangalore University for research facilities.

References

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Volume 67| Part 11| November 2011| Pages o2996-o2997

doi:10.1107/S1600536811042279

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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-(4-fluoro­phen­yl)prop-2-en-1-one

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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