(1E,4E)-1,5-Bis[2-(trifluoro­meth­yl)phen­yl]penta-1,4-dien-3-one

Park, D.H.; Ramkumar, V.; Parthiban, P.

doi:10.1107/S1600536812051586

organic compounds

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ISSN: 2056-9890

Volume 69| Part 2| February 2013| Page o177

doi:10.1107/S1600536812051586

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(1E,4E)-1,5-Bis[2-(trifluoromethyl)phenyl]penta-1,4-dien-3-one

Dong Ho Park,^a V. Ramkumar ^b and P. Parthiban ^a ^*

^aDepartment of Biomedicinal Chemistry, Inje University, Gimhae, Gyeongnam 621 749, Republic of Korea, and ^bDepartment of Chemistry, IIT Madras, Chennai 600 036, TamilNadu, India
^*Correspondence e-mail: parthisivam@yahoo.co.in

(Received 25 November 2012; accepted 21 December 2012; online 4 January 2013)

In the title compound, C₁₉H₁₂F₆O, a monoketone derivative of curcumin, both double bonds have a trans conformation. The molecule is mostly planar with all C and O atoms essentially coplanar, with the exception of one benzene ring, which is tilted by 17.18 (1)° with respect to the plane of the remainder of the molecule. The r.m.s. deviation from planarity of the coplanar section is 0.0097 Å. The crystal packing features weak C—H⋯O and C—H⋯F interactions.

Related literature

For the synthesis of chalcones, see: Tully et al. (2001 ). For the biological properties of chalcones, see: Buescher & Yang (2000 ); Kumar et al. (2003 ), Hsu & Cheng (2007 ). For their physical properties, see: Fichou et al. (1988 ); Butcher et al. (2006 ). For similar structures, see: Butcher et al. (2007 ); Nizam Mohideen et al. (2007 ); Harrison et al. (2006 ).

Experimental

Crystal data

C₁₉H₁₂F₆O
M_r = 370.29
Monoclinic, P c
a = 11.3123 (12) Å
b = 4.7907 (4) Å
c = 15.1697 (16) Å
β = 101.834 (3)°
V = 804.63 (14) Å³
Z = 2
Mo Kα radiation
μ = 0.14 mm⁻¹
T = 298 K
0.35 × 0.25 × 0.10 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.952, T_max = 0.986
5185 measured reflections
2608 independent reflections
1931 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.096
S = 1.04
2608 reflections
235 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17⋯F3ⁱ	0.93	2.62	3.399 (4)	141 (2)
C1—H1⋯O1ⁱⁱ	0.93	2.72	3.290 (5)	121 (1)
Symmetry codes: (i) x-1, y-1, z; (ii) $[x, -y+2, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); 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, 2012); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812051586/zl2522sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812051586/zl2522Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812051586/zl2522Isup3.cml

checkCIF report

Comment top

The title compound is a bischalcone, and is a monoketone derivative of curcumin. Curcumin is a naturally abundant beta-diketone derived from the rizome of curcuma longa (Buescher & Yang, 2000). Numerous studies have shown that curcumin possesses multiple pharmacological properties. Several clinical trials of curcumin were carried out in patients with pancreatic cancer, multiple myeloma, rheumatoid arthritis, cystic fibrosis, inflammatory bowel disease, psoriasis, and other disorders (Kumar et al., 2003; Hsu & Cheng, 2007). Since the stereochemistry of the synthesized molecule is an important criterion for its biological actions, it is of of desirable to establish the structure of the synthesized molecule.

Crystalline chalcone derivatives are also of interest due to their their second harmonic generation properties, particularly, their often are good blue light emitters. The NLO properties of the molecules are also associated with their molecular geometry (Fichou et al., 1988; Butcher et al., 2006), and accordingly, a single-crystal XRD study of the title bischalcone was undertaken to obtain detailed information on its molecular conformation.

In the title compound, C₁₉H₁₂F₆O, both double bonds have trans configuration. The molecule is mostly planar with all carbon and oxygen atoms coplanar with the exception of one phenyl ring (C1—C6), which is tilted by 17.18 (1)° against the plane of the remainder of the molecule. The root mean square deviation from planarity of the coplanar section Ph—C=C—C(O)—C=C (C8—C18) is 0.0097 Å.

The bond lengths of the conjugated chalcone backbone C5—C13 [C5–C8 = 1.460 (4), C8–C9 = 1.322 (4), C9–C10 = 1.460 (4), C10–C11 = 1.470 (4), C11–C12 = 1.311 (4) and C12–C13 = 1.456 Å] show alternate localized single and double bonds as in its ortho-chloro analog (Nizam Mohideen et al., 2007). This indicates the absence of delocalization of the double bonds in the chalcone skeleton C5—C13.

The crystal packing of this molecule is stabilized by weak intermolecular C—H···O, C—H···F and C—H···π interactions (Table 1).

Related literature top

For the synthesis of chalcones, see: Tully et al. (2001). For the biological properties of chalcones, see: Buescher & Yang (2000); Kumar et al. (2003), Hsu & Cheng (2007). For their physical properties, see: Fichou et al. (1988); Butcher et al. (2006). For similar structures, see: Butcher et al. (2007); Nizam Mohideen et al. (2007); Harrison et al. (2006).

Experimental top

The title compound, 1,5-bis(2-(trifluoromethyl)phenyl)penta-1,4-dien-3-one was synthesized by a modified procedure of Tully et al. (2001) using the milder base ammonium acetate instead of sodium hydroxide and a better yield (86%) was obtained. 20 mmol of 2-trifluoromethylbenzaldehyde (2.634 ml), 15 mmol of acetone (1.11 ml) and 1 g of ammonium acetate were combined in one-pot and stirred gently in ethanol as the solvent (20 ml). The complete consumption of the starting materials was monitored by TLC. After completion, the reaction mass was filtered, washed with cold ethanol and dried. The compound was characterized by melting point, IR and NMR. The analytical and spectral data are as reported previously (Tully et al., 2001). X-ray diffraction quality crystals of the title compound were obtained by slow evaporation of an ethanol solution.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Anistropic displacement representation of the molecule with atoms represented with 30% probability ellipsoids.
	Fig. 2. Packing diagram showing C—H···O, C—H···F and C—H···π interactions.

(1E,4E)-1,5-Bis[2-(trifluoromethyl)phenyl]penta-1,4-dien-3-one top

Crystal data top

C₁₉H₁₂F₆O	F(000) = 376
M_r = 370.29	D_x = 1.528 Mg m⁻³
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yc	Cell parameters from 2360 reflections
a = 11.3123 (12) Å	θ = 2.7–24.1°
b = 4.7907 (4) Å	µ = 0.14 mm⁻¹
c = 15.1697 (16) Å	T = 298 K
β = 101.834 (3)°	Block, colourless
V = 804.63 (14) Å³	0.35 × 0.25 × 0.10 mm
Z = 2

Data collection top

Bruker APEXII CCD area-detector diffractometer	2608 independent reflections
Radiation source: fine-focus sealed tube	1931 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
phi and ω scans	θ_max = 27.8°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −14→14
T_min = 0.952, T_max = 0.986	k = −5→5
5185 measured 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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.096	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0351P)² + 0.2469P] where P = (F_o² + 2F_c²)/3
2608 reflections	(Δ/σ)_max < 0.001
235 parameters	Δρ_max = 0.20 e Å⁻³
2 restraints	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₁₉H₁₂F₆O	V = 804.63 (14) Å³
M_r = 370.29	Z = 2
Monoclinic, Pc	Mo Kα radiation
a = 11.3123 (12) Å	µ = 0.14 mm⁻¹
b = 4.7907 (4) Å	T = 298 K
c = 15.1697 (16) Å	0.35 × 0.25 × 0.10 mm
β = 101.834 (3)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	2608 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	1931 reflections with I > 2σ(I)
T_min = 0.952, T_max = 0.986	R_int = 0.020
5185 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	2 restraints
wR(F²) = 0.096	H-atom parameters constrained
S = 1.04	Δρ_max = 0.20 e Å⁻³
2608 reflections	Δρ_min = −0.14 e Å⁻³
235 parameters

Special details top

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
C1	1.1775 (4)	1.5554 (9)	1.1292 (2)	0.0761 (11)
H1	1.1342	1.5756	1.1747	0.091*
C2	1.2832 (4)	1.6949 (8)	1.1343 (2)	0.0784 (11)
H2	1.3110	1.8160	1.1819	0.094*
C3	1.3481 (3)	1.6560 (7)	1.0689 (2)	0.0673 (9)
H3	1.4220	1.7461	1.0736	0.081*
C4	1.3062 (3)	1.4847 (6)	0.9956 (2)	0.0501 (7)
C5	1.1957 (2)	1.3456 (6)	0.98898 (19)	0.0466 (7)
C6	1.1349 (3)	1.3854 (7)	1.0575 (2)	0.0619 (9)
H6	1.0619	1.2933	1.0549	0.074*
C7	1.3802 (3)	1.4515 (8)	0.9268 (2)	0.0654 (10)
C8	1.1460 (3)	1.1721 (7)	0.9110 (2)	0.0533 (8)
H8	1.1829	1.1877	0.8618	0.064*
C9	1.0547 (3)	0.9955 (7)	0.9024 (2)	0.0508 (8)
H9	1.0168	0.9688	0.9507	0.061*
C10	1.0119 (3)	0.8412 (7)	0.8190 (2)	0.0492 (7)
C11	0.9120 (3)	0.6426 (6)	0.81579 (19)	0.0505 (8)
H11	0.8802	0.6177	0.8671	0.061*
C12	0.8662 (3)	0.4996 (6)	0.7433 (2)	0.0478 (7)
H12	0.9004	0.5317	0.6934	0.057*
C13	0.7685 (2)	0.2965 (6)	0.73090 (18)	0.0420 (6)
C14	0.7286 (2)	0.1566 (6)	0.64946 (17)	0.0428 (7)
C15	0.6361 (3)	−0.0368 (6)	0.6405 (2)	0.0540 (8)
H15	0.6105	−0.1284	0.5859	0.065*
C16	0.5820 (3)	−0.0946 (7)	0.7110 (2)	0.0617 (9)
H16	0.5208	−0.2272	0.7047	0.074*
C17	0.6184 (3)	0.0439 (7)	0.7910 (2)	0.0595 (8)
H17	0.5806	0.0084	0.8388	0.071*
C18	0.7107 (3)	0.2348 (7)	0.80077 (19)	0.0518 (8)
H18	0.7351	0.3253	0.8557	0.062*
C19	0.7851 (3)	0.2061 (7)	0.5705 (2)	0.0578 (8)
F1	1.3299 (2)	1.5590 (5)	0.84801 (15)	0.0944 (7)
F2	1.4881 (2)	1.5699 (6)	0.94957 (17)	0.1057 (9)
F3	1.4031 (2)	1.1853 (6)	0.9114 (2)	0.1095 (9)
F4	0.7781 (2)	0.4718 (5)	0.54360 (14)	0.0860 (7)
F5	0.89964 (19)	0.1390 (5)	0.58521 (14)	0.0902 (7)
F6	0.7316 (2)	0.0638 (5)	0.49807 (13)	0.0954 (7)
O1	1.0559 (2)	0.8784 (5)	0.75344 (16)	0.0824 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.083 (3)	0.090 (3)	0.058 (2)	−0.016 (2)	0.0204 (19)	−0.011 (2)
C2	0.096 (3)	0.076 (3)	0.059 (2)	−0.025 (2)	0.005 (2)	−0.0118 (19)
C3	0.063 (2)	0.073 (2)	0.060 (2)	−0.0199 (18)	−0.0003 (17)	0.0054 (19)
C4	0.0462 (15)	0.0481 (18)	0.0545 (18)	−0.0042 (14)	0.0065 (13)	0.0089 (15)
C5	0.0479 (17)	0.0427 (17)	0.0481 (17)	0.0016 (13)	0.0076 (14)	0.0024 (14)
C6	0.061 (2)	0.068 (2)	0.058 (2)	−0.0144 (16)	0.0168 (16)	−0.0079 (17)
C7	0.057 (2)	0.067 (3)	0.073 (2)	−0.0142 (19)	0.0140 (17)	−0.0020 (19)
C8	0.0503 (17)	0.054 (2)	0.0572 (19)	−0.0016 (15)	0.0149 (14)	−0.0019 (15)
C9	0.0577 (18)	0.0486 (18)	0.0474 (17)	−0.0004 (14)	0.0138 (14)	−0.0002 (13)
C10	0.0544 (18)	0.0456 (19)	0.0466 (17)	0.0013 (14)	0.0080 (14)	−0.0025 (14)
C11	0.0614 (19)	0.0500 (19)	0.0408 (17)	−0.0002 (15)	0.0124 (14)	−0.0058 (13)
C12	0.0562 (18)	0.0440 (18)	0.0439 (16)	−0.0005 (14)	0.0119 (14)	−0.0004 (13)
C13	0.0470 (15)	0.0385 (16)	0.0404 (15)	0.0054 (13)	0.0089 (12)	−0.0002 (12)
C14	0.0504 (16)	0.0353 (16)	0.0416 (16)	0.0080 (13)	0.0070 (13)	−0.0015 (12)
C15	0.0589 (18)	0.0463 (18)	0.0511 (18)	0.0045 (16)	−0.0021 (15)	−0.0066 (15)
C16	0.0523 (18)	0.056 (2)	0.074 (2)	−0.0040 (16)	0.0067 (16)	0.0041 (17)
C17	0.0603 (19)	0.060 (2)	0.062 (2)	0.0020 (17)	0.0219 (16)	0.0124 (17)
C18	0.0622 (19)	0.0524 (19)	0.0420 (17)	−0.0007 (15)	0.0134 (14)	−0.0028 (14)
C19	0.070 (2)	0.056 (2)	0.0466 (19)	0.0075 (17)	0.0097 (16)	−0.0062 (16)
F1	0.1087 (16)	0.114 (2)	0.0642 (14)	−0.0084 (15)	0.0272 (12)	0.0071 (13)
F2	0.0714 (14)	0.133 (2)	0.120 (2)	−0.0401 (15)	0.0359 (13)	−0.0138 (16)
F3	0.1025 (17)	0.0725 (17)	0.176 (3)	0.0065 (13)	0.0802 (17)	−0.0137 (16)
F4	0.135 (2)	0.0631 (15)	0.0670 (12)	0.0083 (14)	0.0377 (12)	0.0116 (11)
F5	0.0785 (14)	0.1231 (19)	0.0772 (13)	0.0270 (13)	0.0352 (11)	−0.0012 (14)
F6	0.1393 (18)	0.0984 (17)	0.0467 (11)	−0.0143 (15)	0.0144 (12)	−0.0244 (12)
O1	0.0925 (18)	0.0963 (19)	0.0667 (16)	−0.0401 (16)	0.0356 (14)	−0.0247 (14)

Geometric parameters (Å, º) top

C1—C2	1.358 (5)	C10—C11	1.470 (4)
C1—C6	1.366 (5)	C11—C12	1.310 (4)
C1—H1	0.9300	C11—H11	0.9300
C2—C3	1.362 (5)	C12—C13	1.456 (4)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.385 (4)	C13—C18	1.386 (4)
C3—H3	0.9300	C13—C14	1.397 (4)
C4—C5	1.401 (4)	C14—C15	1.383 (4)
C4—C7	1.474 (5)	C14—C19	1.488 (4)
C5—C6	1.372 (4)	C15—C16	1.364 (4)
C5—C8	1.460 (4)	C15—H15	0.9300
C6—H6	0.9300	C16—C17	1.371 (5)
C7—F1	1.318 (4)	C16—H16	0.9300
C7—F2	1.326 (4)	C17—C18	1.373 (4)
C7—F3	1.331 (4)	C17—H17	0.9300
C8—C9	1.321 (4)	C18—H18	0.9300
C8—H8	0.9300	C19—F5	1.309 (4)
C9—C10	1.460 (4)	C19—F6	1.329 (4)
C9—H9	0.9300	C19—F4	1.334 (4)
C10—O1	1.213 (4)

C2—C1—C6	120.1 (4)	C9—C10—C11	118.2 (3)
C2—C1—H1	119.9	C12—C11—C10	122.4 (3)
C6—C1—H1	119.9	C12—C11—H11	118.8
C1—C2—C3	119.4 (3)	C10—C11—H11	118.8
C1—C2—H2	120.3	C11—C12—C13	128.1 (3)
C3—C2—H2	120.3	C11—C12—H12	115.9
C2—C3—C4	121.2 (3)	C13—C12—H12	115.9
C2—C3—H3	119.4	C18—C13—C14	117.2 (3)
C4—C3—H3	119.4	C18—C13—C12	120.6 (2)
C3—C4—C5	119.5 (3)	C14—C13—C12	122.3 (3)
C3—C4—C7	118.8 (3)	C15—C14—C13	120.6 (3)
C5—C4—C7	121.7 (3)	C15—C14—C19	118.0 (3)
C6—C5—C4	117.3 (3)	C13—C14—C19	121.4 (3)
C6—C5—C8	121.5 (3)	C16—C15—C14	120.8 (3)
C4—C5—C8	121.2 (3)	C16—C15—H15	119.6
C1—C6—C5	122.4 (3)	C14—C15—H15	119.6
C1—C6—H6	118.8	C15—C16—C17	119.6 (3)
C5—C6—H6	118.8	C15—C16—H16	120.2
F1—C7—F2	105.8 (3)	C17—C16—H16	120.2
F1—C7—F3	106.2 (3)	C16—C17—C18	120.1 (3)
F2—C7—F3	104.7 (3)	C16—C17—H17	120.0
F1—C7—C4	113.4 (3)	C18—C17—H17	120.0
F2—C7—C4	113.3 (3)	C17—C18—C13	121.8 (3)
F3—C7—C4	112.7 (3)	C17—C18—H18	119.1
C9—C8—C5	127.5 (3)	C13—C18—H18	119.1
C9—C8—H8	116.3	F5—C19—F6	106.4 (3)
C5—C8—H8	116.3	F5—C19—F4	106.3 (3)
C8—C9—C10	121.6 (3)	F6—C19—F4	104.4 (3)
C8—C9—H9	119.2	F5—C19—C14	113.4 (3)
C10—C9—H9	119.2	F6—C19—C14	112.7 (3)
O1—C10—C9	121.2 (3)	F4—C19—C14	112.9 (3)
O1—C10—C11	120.7 (3)

C6—C1—C2—C3	−2.3 (6)	O1—C10—C11—C12	−0.3 (5)
C1—C2—C3—C4	2.4 (6)	C9—C10—C11—C12	178.6 (3)
C2—C3—C4—C5	−0.9 (5)	C10—C11—C12—C13	179.6 (3)
C2—C3—C4—C7	179.7 (4)	C11—C12—C13—C18	0.5 (4)
C3—C4—C5—C6	−0.7 (4)	C11—C12—C13—C14	−179.6 (3)
C7—C4—C5—C6	178.6 (3)	C18—C13—C14—C15	−0.7 (4)
C3—C4—C5—C8	177.5 (3)	C12—C13—C14—C15	179.5 (3)
C7—C4—C5—C8	−3.1 (4)	C18—C13—C14—C19	−179.5 (3)
C2—C1—C6—C5	0.7 (6)	C12—C13—C14—C19	0.6 (4)
C4—C5—C6—C1	0.8 (5)	C13—C14—C15—C16	0.0 (4)
C8—C5—C6—C1	−177.4 (3)	C19—C14—C15—C16	178.9 (3)
C3—C4—C7—F1	−113.3 (3)	C14—C15—C16—C17	1.1 (5)
C5—C4—C7—F1	67.3 (4)	C15—C16—C17—C18	−1.5 (5)
C3—C4—C7—F2	7.4 (5)	C16—C17—C18—C13	0.8 (5)
C5—C4—C7—F2	−172.0 (3)	C14—C13—C18—C17	0.2 (4)
C3—C4—C7—F3	126.0 (3)	C12—C13—C18—C17	−179.9 (3)
C5—C4—C7—F3	−53.4 (4)	C15—C14—C19—F5	−117.0 (3)
C6—C5—C8—C9	−13.8 (5)	C13—C14—C19—F5	61.9 (4)
C4—C5—C8—C9	168.1 (3)	C15—C14—C19—F6	4.0 (4)
C5—C8—C9—C10	178.0 (3)	C13—C14—C19—F6	−177.1 (3)
C8—C9—C10—O1	−2.9 (5)	C15—C14—C19—F4	121.9 (3)
C8—C9—C10—C11	178.3 (3)	C13—C14—C19—F4	−59.2 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···F3ⁱ	0.93	2.62	3.399 (4)	141 (2)
C1—H1···O1ⁱⁱ	0.93	2.72	3.290 (5)	121 (1)
C3—H3···Cg1	0.93	3.32 (2)	4.096 (3)	142 (1)

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

Experimental details

Crystal data
Chemical formula	C₁₉H₁₂F₆O
M_r	370.29
Crystal system, space group	Monoclinic, Pc
Temperature (K)	298
a, b, c (Å)	11.3123 (12), 4.7907 (4), 15.1697 (16)
β (°)	101.834 (3)
V (Å³)	804.63 (14)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.14
Crystal size (mm)	0.35 × 0.25 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.952, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	5185, 2608, 1931
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.657

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.096, 1.04
No. of reflections	2608
No. of parameters	235
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.14

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···F3ⁱ	0.930	2.62	3.399 (4)	141.4 (18)
C1—H1···O1ⁱⁱ	0.930	2.720	3.290 (5)	120.68 (2)
C3—H3···Cg1	0.930	3.32 (2)	4.096 (3)	141.93 (2)

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

Acknowledgements

The authors acknowledge the Department of Chemistry, IIT Madras, for the X-ray data collection.

References

Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Buescher, R. & Yang, L. (2000). Turmeric in Natural Food Colorants, edited by G. J. Lauro & F. J. Francis, pp. 205–226. New York: Marcel Dekker. Google Scholar
Butcher, R. J., Jasinski, J. P., Sarojini, B. K., Yathirajan, H. S., Bindya, S. & Narayana, B. (2007). Acta Cryst. E63, o3213–o3214. Web of Science CSD CrossRef IUCr Journals Google Scholar
Butcher, R. J., Yathirajan, H. S., Sarojini, B. K., Narayana, B. & Mithun, A. (2006). Acta Cryst. E62, o1629–o1630. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Fichou, D., Watanabe, T., Takeda, T., Miyata, S., Goto, Y. & Nakayama, M. (1988). Jpn J. Appl. Phys. 27, 429–430. CrossRef Web of Science Google Scholar
Harrison, W. T. A., Sarojini, B. K., Vijaya Raj, K. K., Yathirajan, H. S. & Narayana, B. (2006). Acta Cryst. E62, o1522–o1523. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Hsu, C. H. & Cheng, A. L. (2007). Adv. Exp. Med. Biol. 595, 471–480. CrossRef PubMed Google Scholar
Kumar, A. P., Aggarwal, B. B. & Bharti, A. C. (2003). Anticancer Res. 23, 363–398. Web of Science PubMed Google Scholar
Nizam Mohideen, M., Thenmozhi, S., Subbiah Pandi, A., Murugan, R. & Narayanan, S. S. (2007). Acta Cryst. E63, o4379. 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
Tully, W., Main, L. & Nicholson, B. K. (2001). J. Organomet. Chem. 633, 162–172. Web of Science CrossRef CAS Google Scholar