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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 11| November 2011| Pages o2996-o2997

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

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[Liu, J. K. (2006). Chem. Rev. 106, 2209-2223.]) and of chalcones, see: Dhar (1981[Dhar, D. N. (1981). In The Chemistry of Chalcones and Related Compounds. New York: John Wiley.]); Dimmock et al. (1999[Dimmock, J. R., Elias, D. W., Beazely, M. A. & Kandepu, N. M. (1999). Curr. Med. Chem. 6, 1125-1149.]); Satyanarayana et al. (2004[Satyanarayana, M., Tiwari, P., Tripathi, B. K., Sriwastava, A. K. & Pratap, R. (2004). Bioorg. Med. Chem. 12, 883-887.]). For work on the synthesis and strcutures of different chalcone derivatives, see: Samshuddin et al. (2011a[Samshuddin, S., Narayana, B., Shetty, D. N. & Raghavendra, R. (2011a). Der Pharma Chem. 3, 232-240.],b[Samshuddin, S., Butcher, R. J., Akkurt, M., Narayana, B., Yathirajan, H. S. & Sarojini, B. K. (2011b). Acta Cryst. E67, o1954-o1955.]); Fun et al. (2010a[Fun, H.-K., Hemamalini, M., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2010a). Acta Cryst. E66, o582-o583.],b[Fun, H.-K., Hemamalini, M., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2010b). Acta Cryst. E66, o864-o865.]); Jasinski et al. (2010a[Jasinski, J. P., Guild, C. J., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2010a). Acta Cryst. E66, o1948-o1949.],b[Jasinski, J. P., Guild, C. J., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2010b). Acta Cryst. E66, o2018.]); Baktir et al. (2011a[Baktır, Z., Akkurt, M., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2011a). Acta Cryst. E67, o1262-o1263.],b[Baktır, Z., Akkurt, M., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2011b). Acta Cryst. E67, o1292-o1293.]). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]); Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C28H19F3O2

  • Mr = 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)

  • Rint = 0.032

Refinement
  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.102

  • S = 1.04

  • 5218 reflections

  • 299 parameters

  • H-atom parameters constrained

  • Δρmax = 0.30 e Å−3

  • Δρmin = −0.19 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Bruker (2010). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2010[Bruker (2010). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


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.

Refinement top

Carbon-bound H atoms were placed in calculated positions (C—H 0.95 Å for aromatic and vinylic carbon atoms, C—H 0.99 Å for methylene groups) and were included in the refinement in the riding model approximation, with U(H) set to 1.2Ueq(C). The H atoms of the methyl groups were allowed to rotate with a fixed angle around the C—C bond to best fit the experimental electron density (HFIX 137 in the SHELX program suite (Sheldrick, 2008)), with U(H) set to 1.5Ueq(C).

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
[Figure 1] Fig. 1. The molecular structure of the title compound, with atom labels and anisotropic displacement ellipsoids (drawn at 50% probability level).
[Figure 2] Fig. 2. Intermolecular contacts, viewed along [0 1 0]. Symmetry operators: i -x, -y + 2, -z + 1; ii -x + 1, -y + 1, -z.
[Figure 3] 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
C28H19F3O2F(000) = 920
Mr = 444.43Dx = 1.402 Mg m3
Monoclinic, P21/cMelting point: 549 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 22.5742 (5) ÅCell parameters from 9830 reflections
b = 6.8101 (1) Åθ = 3.0–28.3°
c = 13.8475 (3) ŵ = 0.11 mm1
β = 98.405 (1)°T = 200 K
V = 2105.95 (7) Å3Block, yellow
Z = 40.56 × 0.26 × 0.18 mm
Data collection top
Bruker APEXII CCD
diffractometer
4087 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.032
Graphite monochromatorθmax = 28.3°, θmin = 1.8°
ϕ and ω scansh = 3030
35196 measured reflectionsk = 98
5218 independent reflectionsl = 1818
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0462P)2 + 0.5814P]
where P = (Fo2 + 2Fc2)/3
5218 reflections(Δ/σ)max < 0.001
299 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = 0.19 e Å3
Crystal data top
C28H19F3O2V = 2105.95 (7) Å3
Mr = 444.43Z = 4
Monoclinic, P21/cMo Kα radiation
a = 22.5742 (5) ŵ = 0.11 mm1
b = 6.8101 (1) ÅT = 200 K
c = 13.8475 (3) Å0.56 × 0.26 × 0.18 mm
β = 98.405 (1)°
Data collection top
Bruker APEXII CCD
diffractometer
4087 reflections with I > 2σ(I)
35196 measured reflectionsRint = 0.032
5218 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.102H-atom parameters constrained
S = 1.04Δρmax = 0.30 e Å3
5218 reflectionsΔρmin = 0.19 e Å3
299 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
F10.04953 (4)0.88945 (14)0.40789 (7)0.0567 (3)
F20.37032 (4)0.00783 (12)0.22814 (6)0.0486 (2)
F30.53866 (4)1.35725 (17)0.11810 (8)0.0755 (3)
O10.25624 (4)0.57595 (14)0.06967 (7)0.0445 (2)
O20.18161 (4)1.02710 (14)0.05061 (7)0.0422 (2)
C10.25957 (5)0.72789 (19)0.02279 (8)0.0317 (3)
C20.30451 (6)0.88085 (19)0.03214 (9)0.0343 (3)
H20.30151.00370.00070.041*
C30.34907 (5)0.85151 (19)0.08335 (9)0.0342 (3)
H30.34930.72980.11680.041*
C40.15353 (7)1.2144 (2)0.06059 (10)0.0455 (3)
H4A0.16621.29240.00170.068*
H4B0.11001.19770.06950.068*
H4C0.16511.28210.11750.068*
C110.21736 (5)0.76519 (17)0.05006 (8)0.0291 (2)
C120.17663 (5)0.92003 (18)0.03161 (9)0.0313 (3)
C130.13322 (5)0.95422 (18)0.09070 (9)0.0310 (3)
H130.10501.05720.07560.037*
C140.13129 (5)0.83612 (17)0.17253 (8)0.0285 (2)
C150.17348 (5)0.68782 (17)0.19389 (8)0.0287 (2)
H150.17330.61200.25140.034*
C160.21618 (5)0.64726 (17)0.13284 (8)0.0279 (2)
C210.08371 (5)0.86298 (16)0.23502 (9)0.0289 (2)
C220.02421 (5)0.89054 (18)0.19403 (9)0.0331 (3)
H220.01430.90200.12520.040*
C230.02064 (6)0.90140 (18)0.25208 (10)0.0375 (3)
H230.06120.92060.22400.045*
C240.00510 (6)0.88379 (18)0.35085 (10)0.0384 (3)
C250.05286 (6)0.8598 (2)0.39518 (10)0.0398 (3)
H250.06220.85080.46420.048*
C260.09725 (6)0.84925 (18)0.33614 (9)0.0345 (3)
H260.13770.83230.36520.041*
C310.25833 (5)0.48112 (17)0.15868 (8)0.0274 (2)
C320.23728 (5)0.30657 (18)0.19374 (9)0.0312 (3)
H320.19620.29670.20100.037*
C330.27442 (6)0.14721 (18)0.21833 (9)0.0343 (3)
H330.25960.02940.24260.041*
C340.33354 (6)0.16525 (18)0.20640 (9)0.0333 (3)
C350.35695 (5)0.3347 (2)0.17383 (9)0.0352 (3)
H350.39820.34300.16730.042*
C360.31926 (5)0.49307 (18)0.15071 (9)0.0322 (3)
H360.33500.61190.12900.039*
C410.39775 (5)0.9881 (2)0.09336 (9)0.0340 (3)
C420.44727 (6)0.9221 (2)0.13332 (10)0.0425 (3)
H420.44840.78990.15500.051*
C430.49492 (6)1.0455 (3)0.14204 (11)0.0504 (4)
H430.52880.99980.16900.060*
C440.49179 (6)1.2347 (3)0.11076 (11)0.0498 (4)
C450.44382 (7)1.3083 (2)0.07209 (10)0.0473 (3)
H450.44311.44140.05160.057*
C460.39656 (6)1.1840 (2)0.06367 (9)0.0394 (3)
H460.36281.23220.03740.047*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0539 (5)0.0573 (6)0.0682 (6)0.0014 (4)0.0407 (4)0.0098 (4)
F20.0448 (5)0.0415 (5)0.0603 (5)0.0126 (4)0.0102 (4)0.0063 (4)
F30.0552 (6)0.0899 (8)0.0845 (7)0.0380 (5)0.0209 (5)0.0072 (6)
O10.0498 (6)0.0425 (5)0.0458 (5)0.0121 (4)0.0220 (4)0.0141 (4)
O20.0514 (6)0.0377 (5)0.0416 (5)0.0052 (4)0.0203 (4)0.0118 (4)
C10.0316 (6)0.0353 (6)0.0295 (6)0.0033 (5)0.0092 (5)0.0003 (5)
C20.0372 (6)0.0345 (6)0.0334 (6)0.0059 (5)0.0125 (5)0.0022 (5)
C30.0348 (6)0.0366 (7)0.0327 (6)0.0028 (5)0.0096 (5)0.0012 (5)
C40.0596 (9)0.0370 (7)0.0394 (7)0.0012 (6)0.0055 (6)0.0090 (6)
C110.0291 (6)0.0289 (6)0.0308 (6)0.0061 (4)0.0092 (4)0.0028 (5)
C120.0347 (6)0.0288 (6)0.0317 (6)0.0053 (5)0.0093 (5)0.0011 (5)
C130.0309 (6)0.0272 (6)0.0359 (6)0.0006 (5)0.0080 (5)0.0006 (5)
C140.0283 (6)0.0271 (6)0.0313 (6)0.0057 (4)0.0085 (4)0.0040 (4)
C150.0298 (6)0.0285 (6)0.0295 (5)0.0044 (5)0.0094 (4)0.0002 (5)
C160.0275 (5)0.0268 (6)0.0305 (6)0.0056 (4)0.0075 (4)0.0033 (4)
C210.0305 (6)0.0228 (5)0.0351 (6)0.0024 (4)0.0113 (5)0.0027 (5)
C220.0349 (6)0.0289 (6)0.0367 (6)0.0008 (5)0.0090 (5)0.0008 (5)
C230.0310 (6)0.0302 (6)0.0534 (8)0.0008 (5)0.0129 (6)0.0041 (6)
C240.0425 (7)0.0290 (6)0.0498 (8)0.0018 (5)0.0273 (6)0.0070 (5)
C250.0493 (8)0.0382 (7)0.0348 (6)0.0004 (6)0.0163 (6)0.0049 (5)
C260.0351 (6)0.0342 (6)0.0355 (6)0.0002 (5)0.0090 (5)0.0046 (5)
C310.0286 (6)0.0287 (6)0.0260 (5)0.0036 (4)0.0082 (4)0.0045 (4)
C320.0295 (6)0.0325 (6)0.0335 (6)0.0035 (5)0.0109 (5)0.0020 (5)
C330.0387 (7)0.0291 (6)0.0365 (6)0.0036 (5)0.0102 (5)0.0008 (5)
C340.0357 (6)0.0325 (6)0.0318 (6)0.0048 (5)0.0055 (5)0.0028 (5)
C350.0270 (6)0.0419 (7)0.0376 (6)0.0010 (5)0.0083 (5)0.0023 (5)
C360.0300 (6)0.0329 (6)0.0349 (6)0.0057 (5)0.0090 (5)0.0005 (5)
C410.0303 (6)0.0427 (7)0.0301 (6)0.0032 (5)0.0081 (5)0.0049 (5)
C420.0388 (7)0.0474 (8)0.0442 (7)0.0004 (6)0.0156 (6)0.0041 (6)
C430.0335 (7)0.0685 (10)0.0521 (8)0.0030 (7)0.0164 (6)0.0089 (8)
C440.0392 (7)0.0645 (10)0.0459 (8)0.0186 (7)0.0070 (6)0.0121 (7)
C450.0503 (8)0.0474 (8)0.0445 (8)0.0137 (7)0.0075 (6)0.0031 (6)
C460.0383 (7)0.0447 (7)0.0367 (7)0.0048 (6)0.0106 (5)0.0014 (6)
Geometric parameters (Å, º) top
F1—C241.3648 (14)C22—H220.9500
F2—C341.3624 (14)C23—C241.367 (2)
F3—C441.3628 (16)C23—H230.9500
O1—C11.2180 (15)C24—C251.371 (2)
O2—C121.3704 (14)C25—C261.3847 (17)
O2—C41.4218 (17)C25—H250.9500
C1—C21.4729 (17)C26—H260.9500
C1—C111.5070 (16)C31—C321.3936 (16)
C2—C31.3278 (17)C31—C361.3981 (16)
C2—H20.9500C32—C331.3832 (17)
C3—C411.4617 (17)C32—H320.9500
C3—H30.9500C33—C341.3741 (18)
C4—H4A0.9800C33—H330.9500
C4—H4B0.9800C34—C351.3728 (18)
C4—H4C0.9800C35—C361.3818 (18)
C11—C121.3979 (17)C35—H350.9500
C11—C161.4030 (16)C36—H360.9500
C12—C131.3849 (17)C41—C421.3925 (18)
C13—C141.3954 (17)C41—C461.3974 (19)
C13—H130.9500C42—C431.384 (2)
C14—C151.3900 (16)C42—H420.9500
C14—C211.4859 (15)C43—C441.365 (2)
C15—C161.3995 (16)C43—H430.9500
C15—H150.9500C44—C451.371 (2)
C16—C311.4880 (16)C45—C461.3802 (19)
C21—C261.3920 (17)C45—H450.9500
C21—C221.3923 (17)C46—H460.9500
C22—C231.3836 (18)
C12—O2—C4117.93 (10)F1—C24—C25118.55 (12)
O1—C1—C2122.93 (11)C23—C24—C25123.16 (12)
O1—C1—C11120.28 (11)C24—C25—C26117.86 (12)
C2—C1—C11116.78 (10)C24—C25—H25121.1
C3—C2—C1121.72 (12)C26—C25—H25121.1
C3—C2—H2119.1C25—C26—C21121.26 (12)
C1—C2—H2119.1C25—C26—H26119.4
C2—C3—C41126.41 (12)C21—C26—H26119.4
C2—C3—H3116.8C32—C31—C36117.82 (11)
C41—C3—H3116.8C32—C31—C16119.58 (10)
O2—C4—H4A109.5C36—C31—C16122.59 (10)
O2—C4—H4B109.5C33—C32—C31121.98 (11)
H4A—C4—H4B109.5C33—C32—H32119.0
O2—C4—H4C109.5C31—C32—H32119.0
H4A—C4—H4C109.5C34—C33—C32117.69 (11)
H4B—C4—H4C109.5C34—C33—H33121.2
C12—C11—C16119.38 (10)C32—C33—H33121.2
C12—C11—C1117.91 (10)F2—C34—C35118.87 (11)
C16—C11—C1122.67 (11)F2—C34—C33118.31 (11)
O2—C12—C13123.54 (11)C35—C34—C33122.81 (12)
O2—C12—C11114.93 (10)C34—C35—C36118.60 (11)
C13—C12—C11121.48 (11)C34—C35—H35120.7
C12—C13—C14119.45 (11)C36—C35—H35120.7
C12—C13—H13120.3C35—C36—C31121.05 (11)
C14—C13—H13120.3C35—C36—H36119.5
C15—C14—C13119.33 (10)C31—C36—H36119.5
C15—C14—C21119.78 (10)C42—C41—C46118.44 (12)
C13—C14—C21120.87 (11)C42—C41—C3119.38 (12)
C14—C15—C16121.73 (11)C46—C41—C3122.19 (12)
C14—C15—H15119.1C43—C42—C41121.19 (14)
C16—C15—H15119.1C43—C42—H42119.4
C15—C16—C11118.53 (11)C41—C42—H42119.4
C15—C16—C31118.53 (10)C44—C43—C42117.95 (14)
C11—C16—C31122.95 (10)C44—C43—H43121.0
C26—C21—C22118.43 (11)C42—C43—H43121.0
C26—C21—C14120.42 (11)F3—C44—C43118.54 (14)
C22—C21—C14121.03 (11)F3—C44—C45118.12 (15)
C23—C22—C21120.96 (12)C43—C44—C45123.35 (13)
C23—C22—H22119.5C44—C45—C46118.22 (15)
C21—C22—H22119.5C44—C45—H45120.9
C24—C23—C22118.31 (12)C46—C45—H45120.9
C24—C23—H23120.8C45—C46—C41120.84 (13)
C22—C23—H23120.8C45—C46—H46119.6
F1—C24—C23118.29 (12)C41—C46—H46119.6
O1—C1—C2—C38.7 (2)C22—C23—C24—C251.34 (19)
C11—C1—C2—C3170.25 (12)F1—C24—C25—C26178.35 (11)
C1—C2—C3—C41176.55 (12)C23—C24—C25—C261.3 (2)
O1—C1—C11—C12114.77 (14)C24—C25—C26—C210.17 (19)
C2—C1—C11—C1266.28 (15)C22—C21—C26—C250.88 (18)
O1—C1—C11—C1662.99 (16)C14—C21—C26—C25175.32 (11)
C2—C1—C11—C16115.96 (13)C15—C16—C31—C3240.84 (15)
C4—O2—C12—C1319.08 (18)C11—C16—C31—C32139.22 (12)
C4—O2—C12—C11163.68 (11)C15—C16—C31—C36138.15 (12)
C16—C11—C12—O2179.64 (10)C11—C16—C31—C3641.80 (17)
C1—C11—C12—O22.53 (15)C36—C31—C32—C331.33 (17)
C16—C11—C12—C133.06 (17)C16—C31—C32—C33179.63 (11)
C1—C11—C12—C13174.78 (11)C31—C32—C33—C340.47 (18)
O2—C12—C13—C14179.37 (11)C32—C33—C34—F2178.47 (11)
C11—C12—C13—C142.30 (18)C32—C33—C34—C351.67 (19)
C12—C13—C14—C150.79 (17)F2—C34—C35—C36179.18 (11)
C12—C13—C14—C21177.28 (11)C33—C34—C35—C360.96 (19)
C13—C14—C15—C163.16 (17)C34—C35—C36—C310.97 (18)
C21—C14—C15—C16174.93 (10)C32—C31—C36—C352.07 (17)
C14—C15—C16—C112.39 (17)C16—C31—C36—C35178.93 (11)
C14—C15—C16—C31177.66 (10)C2—C3—C41—C42167.43 (13)
C12—C11—C16—C150.71 (16)C2—C3—C41—C4612.3 (2)
C1—C11—C16—C15177.02 (10)C46—C41—C42—C431.2 (2)
C12—C11—C16—C31179.24 (10)C3—C41—C42—C43178.53 (13)
C1—C11—C16—C313.03 (17)C41—C42—C43—C440.4 (2)
C15—C14—C21—C2641.88 (16)C42—C43—C44—F3179.40 (13)
C13—C14—C21—C26140.05 (12)C42—C43—C44—C450.5 (2)
C15—C14—C21—C22134.22 (12)F3—C44—C45—C46179.36 (13)
C13—C14—C21—C2243.84 (16)C43—C44—C45—C460.6 (2)
C26—C21—C22—C230.87 (18)C44—C45—C46—C410.3 (2)
C14—C21—C22—C23175.31 (11)C42—C41—C46—C451.16 (19)
C21—C22—C23—C240.20 (18)C3—C41—C46—C45178.57 (12)
C22—C23—C24—F1178.34 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C25—H25···F1i0.952.553.2276 (15)129
C43—H43···F2ii0.952.533.4449 (16)161
Symmetry codes: (i) x, y+2, z+1; (ii) x+1, y+1, z.

Experimental details

Crystal data
Chemical formulaC28H19F3O2
Mr444.43
Crystal system, space groupMonoclinic, P21/c
Temperature (K)200
a, b, c (Å)22.5742 (5), 6.8101 (1), 13.8475 (3)
β (°) 98.405 (1)
V3)2105.95 (7)
Z4
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.56 × 0.26 × 0.18
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
35196, 5218, 4087
Rint0.032
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.102, 1.04
No. of reflections5218
No. of parameters299
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
C25—H25···F1i0.952.553.2276 (15)128.5
C43—H43···F2ii0.952.533.4449 (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
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