(E)-1-(3,5-Difluoro­phen­yl)-3-(2,4-dimeth­oxy­phen­yl)prop-2-en-1-one

Huang, T.; Zhang, D.; Yang, Q.; Wei, X.; Wu, J.

doi:10.1107/S1600536810035257

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page o2518

doi:10.1107/S1600536810035257

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(E)-1-(3,5-Difluorophenyl)-3-(2,4-dimethoxyphenyl)prop-2-en-1-one

Tanxiao Huang,^a Dongdong Zhang,^b Quanzhi Yang,^a Xiaoyan Wei ^a and Jianzhang Wu ^a,^c ^*

^aSchool of Pharmacy, Wenzhou Medical College, Wenzhou, Zhejiang Province 325035, People's Republic of China, ^bLife Science College, Wenzhou Medical College, Wenzhou, Zhejiang Province 325035, People's Republic of China, and ^cInstitute of Biotechnology, Nanjing University of Science and Technology, Nanjing, Jiangsu Province 210094, People's Republic of China
^*Correspondence e-mail: wujianzhang6@163.com

(Received 4 August 2010; accepted 1 September 2010; online 8 September 2010)

The title compound, C₁₇H₁₄F₂O₃, is approximately planar, the dihedral angle between the rings being 5.46 (2)°. The H atoms of the central propenone group are trans. The crystal structure is stabilized by intermolecular C—H⋯F hydrogen bonds.

Related literature

For related structures, see: Peng et al. (2010 ); Wu, Zhang et al. (2009 ); Liang et al. (2007 ); Yathirajan et al. (2006 ). For background to and applications of chalcones, see: Nowakowska (2007 ); Nielsen et al. (2005 ); Wu, Qiu et al. (2009 ); Liang et al. (2009 ); Mojzisa et al. (2008 ); Liu et al. (2008 ); Wu et al. (2010 ); Zhao et al. (2010 ); Selvakumar et al. (2007 ).

Experimental

Crystal data

C₁₇H₁₄F₂O₃
M_r = 304.28
Triclinic, $[P \overline 1]$
a = 7.8047 (8) Å
b = 11.2591 (12) Å
c = 17.0080 (18) Å
α = 81.407 (2)°
β = 81.231 (2)°
γ = 76.319 (2)°
V = 1425.1 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.27 × 0.22 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.602, T_max = 1.000
7600 measured reflections
5242 independent reflections
2815 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.162
S = 0.92
5242 reflections
401 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C25—H25⋯F4ⁱ	0.93	2.59	3.375 (3)	142
C13—H13⋯F4ⁱⁱ	0.93	2.46	3.303 (4)	151
C9—H9⋯F3ⁱⁱⁱ	0.93	2.66	3.532 (3)	156
C30—H30⋯F2ⁱⁱ	0.93	2.47	3.303 (4)	149
C8—H8⋯F2ⁱ	0.93	2.46	3.369 (3)	166
C28—H28⋯F1ⁱⁱⁱ	0.93	2.53	3.437 (3)	166
Symmetry codes: (i) x+1, y-1, z; (ii) -x-1, -y+2, -z+2; (iii) -x, -y+1, -z+2.

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810035257/pb2039sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810035257/pb2039Isup2.hkl

checkCIF report

Comment top

Chalcones, which have the common Skeleton of 1,3-diaryl-2-propen-1-ones, are open-chain flavonoids. Chalcones belong to nature products and distribute widespread in fruits, vegetables, tea and so on. Like as other flavonoids, Chalcones have wide-range biological properties, including antimicrobial, antitumor, antiangiogenic, antifungal, antioxidant activities and so on (Nowakowska, 2007; Zhao et al., 2010; Liu et al., 2008; Wu et al., 2010.). Moreover, Chalcones have low toxicity. Owing to its good effect and low toxicity, it has attract more and more scientists attention. Recent studies have demonstrated that synthesized Chalcones have the same activities as or better activities than natural chalcones (Nowakowska, 2007; Selvakumar et al., 2007).

Because Chalcones have good activity, the title chalcone derivative has been synthesized. In order to get detailed information such as the geometrical features and the underlying interaction of the crystal structure, an X-ray study of the title compound was carried out.

Two rings of molecule is approximately planar and the dihedral angle between the two rings is 5.46°. The H atoms of the central propenone group are trans. The average value of exocyclic bond angles [120.7 (4)°] and the bond distances [1.381 (5) Å] in the phenyl rings are agree quite well with the normal values reported in the literature for some analogous structures (Peng et al., 2010; Wu et al., 2009; Liang et al., 2007; Yathirajan et al., 2006). In the crystal, The crystal structure is stabilized by intermolecular C—H···F hydrogen bonds.

Related literature top

For related structures, see: Peng et al. (2010); Wu, Zhang et al. (2009); Liang et al. (2007); Yathirajan et al. (2006). For background to and applications of chalcones, see: Nowakowska (2007); Nielsen et al. (2005); Wu, Qiu et al. (2009); Liang et al. (2009); Mojzisa et al. (2008); Liu et al. (2008); Wu et al. (2010); Zhao et al. (2010); Selvakumar et al. (2007).

Experimental top

The title compounds was synthesized by Claisene-Schmidt condensation. 2,4-dimethoxyBenzaldehyde (2 mmol) and 3',5'-Difluoroacetophenone (2 mmol) were dissolved in ehanol (20 ml). Temperature of reaction was controlled at 278 K and 5 drops NaOH (20%) was added. The reaction was monitored by thin-layer chromatography. 20 ml H₂O was added after 8 h and the yellow solid was Precipitated, washed with water and cold ethanol, dried and purified by column chromatography on silica gel. Single crystals of the title compound were grow in a CH₂Cl₂/CH₃CH₂OH mixture (2:1) at 277 K.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Ellispoid plot.
	Fig. 2. Packing diagram.

(E)-1-(3,5-Difluorophenyl)-3-(2,4-dimethoxyphenyl)prop-2-en-1-one top

Crystal data top

C₁₇H₁₄F₂O₃	Z = 4
M_r = 304.28	F(000) = 632
Triclinic, P1	D_x = 1.418 Mg m⁻³
a = 7.8047 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.2591 (12) Å	Cell parameters from 1503 reflections
c = 17.0080 (18) Å	θ = 4.7–46.3°
α = 81.407 (2)°	µ = 0.11 mm⁻¹
β = 81.231 (2)°	T = 293 K
γ = 76.319 (2)°	Prismatic, green
V = 1425.1 (3) Å³	0.27 × 0.22 × 0.17 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	5242 independent reflections
Radiation source: fine-focus sealed tube	2815 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
phi and ω scans	θ_max = 25.5°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.602, T_max = 1.000	k = −6→13
7600 measured reflections	l = −20→20

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.162	H-atom parameters constrained
S = 0.92	w = 1/[σ²(F_o²) + (0.0748P)²] where P = (F_o² + 2F_c²)/3
5242 reflections	(Δ/σ)_max = 0.005
401 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₇H₁₄F₂O₃	γ = 76.319 (2)°
M_r = 304.28	V = 1425.1 (3) Å³
Triclinic, P1	Z = 4
a = 7.8047 (8) Å	Mo Kα radiation
b = 11.2591 (12) Å	µ = 0.11 mm⁻¹
c = 17.0080 (18) Å	T = 293 K
α = 81.407 (2)°	0.27 × 0.22 × 0.17 mm
β = 81.231 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	5242 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2815 reflections with I > 2σ(I)
T_min = 0.602, T_max = 1.000	R_int = 0.034
7600 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.162	H-atom parameters constrained
S = 0.92	Δρ_max = 0.24 e Å⁻³
5242 reflections	Δρ_min = −0.20 e Å⁻³
401 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
F1	−0.1189 (2)	0.41876 (16)	1.15514 (9)	0.0680 (5)
F2	−0.4957 (2)	0.73654 (16)	1.01469 (11)	0.0774 (6)
F3	−0.1962 (3)	0.85773 (17)	0.95482 (10)	0.0765 (6)
F4	−0.5094 (3)	1.19504 (18)	0.80248 (13)	0.1043 (8)
O1	−0.2308 (3)	0.4469 (2)	0.81479 (12)	0.0796 (8)
O2	0.0468 (3)	0.10719 (18)	0.67405 (11)	0.0612 (6)
O3	0.4032 (3)	−0.26852 (18)	0.79562 (12)	0.0638 (6)
O4	−0.2520 (3)	0.8979 (2)	0.60758 (13)	0.0763 (7)
O5	0.1805 (3)	0.61876 (18)	0.46058 (11)	0.0595 (6)
O6	0.4537 (3)	0.21210 (18)	0.57760 (12)	0.0621 (6)
C1	−0.1733 (4)	0.3926 (3)	0.87639 (17)	0.0503 (8)
C2	−0.0645 (4)	0.2671 (3)	0.87879 (17)	0.0534 (8)
H2	−0.0239	0.2287	0.9269	0.064*
C3	−0.0216 (4)	0.2062 (3)	0.81555 (17)	0.0478 (8)
H3	−0.0661	0.2473	0.7688	0.057*
C4	0.0863 (4)	0.0833 (3)	0.81000 (16)	0.0433 (7)
C5	0.1221 (4)	0.0337 (3)	0.73634 (16)	0.0469 (7)
C6	0.2271 (4)	−0.0839 (3)	0.72881 (17)	0.0494 (8)
H6	0.2496	−0.1154	0.6798	0.059*
C7	0.2975 (4)	−0.1533 (3)	0.79590 (18)	0.0492 (8)
C8	0.2621 (4)	−0.1065 (3)	0.86926 (18)	0.0580 (9)
H8	0.3096	−0.1533	0.9139	0.070*
C9	0.1576 (4)	0.0082 (3)	0.87555 (17)	0.0525 (8)
H9	0.1329	0.0374	0.9253	0.063*
C10	−0.2167 (3)	0.4558 (2)	0.95157 (16)	0.0418 (7)
C11	−0.1461 (4)	0.4034 (3)	1.02204 (16)	0.0457 (7)
H11	−0.0681	0.3269	1.0249	0.055*
C12	−0.1941 (4)	0.4671 (3)	1.08689 (16)	0.0473 (7)
C13	−0.3090 (4)	0.5794 (3)	1.08698 (18)	0.0537 (8)
H13	−0.3390	0.6210	1.1321	0.064*
C14	−0.3774 (4)	0.6268 (3)	1.01672 (18)	0.0503 (8)
C15	−0.3339 (4)	0.5702 (3)	0.94908 (17)	0.0484 (8)
H15	−0.3814	0.6070	0.9022	0.058*
C16	0.0892 (5)	0.0699 (3)	0.59549 (16)	0.0703 (10)
H16A	0.2140	0.0624	0.5787	0.105*
H16B	0.0229	0.1302	0.5589	0.105*
H16C	0.0590	−0.0081	0.5960	0.105*
C17	0.4356 (4)	−0.3267 (3)	0.72383 (19)	0.0662 (9)
H17A	0.3244	−0.3278	0.7067	0.099*
H17B	0.5025	−0.4096	0.7340	0.099*
H17C	0.5018	−0.2817	0.6826	0.099*
C18	−0.2005 (4)	0.8425 (3)	0.67020 (17)	0.0487 (8)
C19	−0.0831 (4)	0.7203 (3)	0.67198 (17)	0.0493 (8)
H19	−0.0649	0.6735	0.7211	0.059*
C20	−0.0021 (4)	0.6746 (3)	0.60528 (17)	0.0466 (7)
H20	−0.0241	0.7249	0.5577	0.056*
C21	0.1172 (4)	0.5552 (2)	0.59737 (16)	0.0423 (7)
C22	0.2083 (3)	0.5271 (3)	0.52183 (16)	0.0430 (7)
C23	0.3202 (3)	0.4129 (2)	0.51277 (16)	0.0467 (7)
H23	0.3787	0.3950	0.4626	0.056*
C24	0.3438 (4)	0.3257 (3)	0.57915 (17)	0.0465 (7)
C25	0.2562 (4)	0.3512 (3)	0.65383 (17)	0.0521 (8)
H25	0.2723	0.2921	0.6981	0.062*
C26	0.1461 (4)	0.4637 (3)	0.66228 (16)	0.0478 (7)
H26	0.0885	0.4800	0.7128	0.057*
C27	−0.2562 (4)	0.9035 (3)	0.74549 (17)	0.0440 (7)
C28	−0.2002 (4)	0.8479 (3)	0.81899 (17)	0.0496 (8)
H28	−0.1295	0.7687	0.8238	0.060*
C29	−0.2513 (4)	0.9119 (3)	0.88340 (17)	0.0500 (8)
C30	−0.3563 (4)	1.0274 (3)	0.88054 (19)	0.0579 (8)
H30	−0.3918	1.0683	0.9259	0.070*
C31	−0.4070 (4)	1.0801 (3)	0.8076 (2)	0.0605 (9)
C32	−0.3603 (4)	1.0222 (3)	0.74061 (19)	0.0562 (8)
H32	−0.3975	1.0615	0.6921	0.067*
C33	0.2640 (4)	0.5973 (3)	0.38187 (16)	0.0594 (9)
H33A	0.3906	0.5764	0.3817	0.089*
H33B	0.2316	0.6703	0.3454	0.089*
H33C	0.2259	0.5307	0.3655	0.089*
C34	0.5535 (4)	0.1789 (3)	0.50357 (19)	0.0704 (10)
H34A	0.4738	0.1760	0.4665	0.106*
H34B	0.6313	0.0996	0.5126	0.106*
H34C	0.6226	0.2390	0.4818	0.106*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0799 (13)	0.0739 (13)	0.0421 (10)	0.0071 (10)	−0.0177 (9)	−0.0090 (9)
F2	0.0863 (14)	0.0563 (12)	0.0775 (13)	0.0256 (10)	−0.0236 (10)	−0.0218 (10)
F3	0.1055 (15)	0.0721 (13)	0.0443 (11)	0.0041 (11)	−0.0221 (10)	−0.0078 (9)
F4	0.139 (2)	0.0618 (13)	0.0955 (16)	0.0442 (13)	−0.0455 (14)	−0.0312 (12)
O1	0.1074 (19)	0.0692 (16)	0.0395 (13)	0.0305 (14)	−0.0166 (12)	−0.0070 (12)
O2	0.0856 (16)	0.0512 (13)	0.0334 (11)	0.0128 (11)	−0.0118 (10)	−0.0025 (10)
O3	0.0758 (15)	0.0462 (13)	0.0605 (14)	0.0126 (11)	−0.0208 (12)	−0.0074 (11)
O4	0.1063 (19)	0.0609 (15)	0.0495 (14)	0.0189 (13)	−0.0280 (13)	−0.0088 (11)
O5	0.0801 (15)	0.0510 (12)	0.0341 (11)	0.0040 (11)	−0.0019 (10)	0.0025 (10)
O6	0.0730 (15)	0.0514 (13)	0.0475 (13)	0.0146 (11)	−0.0073 (11)	−0.0057 (10)
C1	0.0553 (19)	0.0490 (19)	0.0368 (17)	0.0027 (15)	−0.0018 (14)	−0.0004 (14)
C2	0.063 (2)	0.0495 (18)	0.0396 (17)	0.0054 (16)	−0.0091 (14)	−0.0046 (14)
C3	0.0543 (19)	0.0489 (18)	0.0365 (16)	−0.0023 (15)	−0.0075 (13)	−0.0055 (14)
C4	0.0500 (18)	0.0413 (17)	0.0366 (16)	−0.0054 (14)	−0.0070 (13)	−0.0040 (13)
C5	0.0531 (18)	0.0441 (18)	0.0386 (16)	−0.0035 (15)	−0.0053 (13)	−0.0015 (14)
C6	0.0569 (19)	0.0477 (18)	0.0394 (17)	−0.0003 (15)	−0.0050 (14)	−0.0110 (14)
C7	0.0487 (18)	0.0431 (18)	0.0501 (19)	0.0019 (15)	−0.0093 (14)	−0.0033 (15)
C8	0.071 (2)	0.054 (2)	0.0457 (19)	0.0014 (17)	−0.0218 (16)	−0.0033 (16)
C9	0.064 (2)	0.053 (2)	0.0399 (17)	−0.0030 (17)	−0.0128 (15)	−0.0118 (15)
C10	0.0419 (16)	0.0432 (17)	0.0381 (16)	−0.0067 (14)	−0.0013 (12)	−0.0058 (13)
C11	0.0475 (18)	0.0434 (18)	0.0415 (17)	−0.0024 (14)	−0.0048 (13)	−0.0030 (14)
C12	0.0502 (18)	0.0518 (19)	0.0361 (16)	−0.0011 (15)	−0.0101 (14)	−0.0048 (14)
C13	0.057 (2)	0.057 (2)	0.0455 (18)	−0.0047 (17)	−0.0027 (15)	−0.0164 (15)
C14	0.0508 (18)	0.0411 (18)	0.0532 (19)	0.0047 (15)	−0.0058 (15)	−0.0113 (15)
C15	0.0526 (19)	0.0446 (18)	0.0447 (17)	−0.0018 (15)	−0.0106 (14)	−0.0042 (14)
C16	0.108 (3)	0.062 (2)	0.0320 (17)	−0.002 (2)	−0.0128 (17)	−0.0012 (16)
C17	0.075 (2)	0.056 (2)	0.061 (2)	0.0025 (18)	−0.0060 (17)	−0.0159 (17)
C18	0.0531 (19)	0.0466 (18)	0.0455 (18)	−0.0039 (15)	−0.0170 (15)	−0.0028 (15)
C19	0.0575 (19)	0.0464 (18)	0.0402 (17)	0.0019 (15)	−0.0135 (14)	−0.0064 (14)
C20	0.0535 (18)	0.0468 (18)	0.0393 (17)	−0.0069 (15)	−0.0115 (14)	−0.0055 (14)
C21	0.0447 (17)	0.0410 (17)	0.0409 (16)	−0.0057 (14)	−0.0089 (13)	−0.0063 (13)
C22	0.0467 (17)	0.0448 (18)	0.0368 (16)	−0.0072 (14)	−0.0093 (13)	−0.0029 (13)
C23	0.0511 (18)	0.0489 (18)	0.0361 (16)	−0.0026 (15)	−0.0041 (13)	−0.0074 (14)
C24	0.0471 (18)	0.0418 (18)	0.0463 (18)	0.0014 (14)	−0.0100 (14)	−0.0047 (14)
C25	0.0562 (19)	0.0504 (19)	0.0406 (17)	0.0029 (16)	−0.0095 (14)	0.0032 (14)
C26	0.0533 (18)	0.0527 (19)	0.0328 (15)	−0.0035 (15)	−0.0034 (13)	−0.0051 (14)
C27	0.0429 (17)	0.0414 (17)	0.0444 (17)	−0.0010 (14)	−0.0064 (13)	−0.0066 (13)
C28	0.0535 (19)	0.0431 (17)	0.0476 (18)	0.0018 (15)	−0.0099 (14)	−0.0068 (14)
C29	0.0552 (19)	0.0530 (19)	0.0394 (17)	−0.0035 (16)	−0.0105 (14)	−0.0068 (15)
C30	0.062 (2)	0.060 (2)	0.053 (2)	−0.0035 (17)	−0.0097 (16)	−0.0227 (17)
C31	0.064 (2)	0.0454 (19)	0.068 (2)	0.0114 (17)	−0.0215 (18)	−0.0176 (17)
C32	0.062 (2)	0.0478 (19)	0.0529 (19)	0.0042 (16)	−0.0196 (16)	−0.0022 (16)
C33	0.068 (2)	0.070 (2)	0.0328 (16)	−0.0052 (18)	−0.0047 (15)	0.0020 (15)
C34	0.079 (2)	0.062 (2)	0.058 (2)	0.0128 (19)	−0.0041 (18)	−0.0182 (18)

Geometric parameters (Å, º) top

F1—C12	1.363 (3)	C15—H15	0.9300
F2—C14	1.355 (3)	C16—H16A	0.9600
F3—C29	1.359 (3)	C16—H16B	0.9600
F4—C31	1.349 (3)	C16—H16C	0.9600
O1—C1	1.223 (3)	C17—H17A	0.9600
O2—C5	1.360 (3)	C17—H17B	0.9600
O2—C16	1.428 (3)	C17—H17C	0.9600
O3—C7	1.363 (3)	C18—C19	1.461 (4)
O3—C17	1.432 (3)	C18—C27	1.501 (4)
O4—C18	1.224 (3)	C19—C20	1.324 (4)
O5—C22	1.356 (3)	C19—H19	0.9300
O5—C33	1.425 (3)	C20—C21	1.455 (4)
O6—C24	1.362 (3)	C20—H20	0.9300
O6—C34	1.427 (3)	C21—C26	1.399 (4)
C1—C2	1.465 (4)	C21—C22	1.412 (4)
C1—C10	1.510 (4)	C22—C23	1.388 (4)
C2—C3	1.319 (4)	C23—C24	1.385 (3)
C2—H2	0.9300	C23—H23	0.9300
C3—C4	1.448 (4)	C24—C25	1.384 (4)
C3—H3	0.9300	C25—C26	1.366 (4)
C4—C9	1.398 (4)	C25—H25	0.9300
C4—C5	1.410 (4)	C26—H26	0.9300
C5—C6	1.395 (4)	C27—C32	1.388 (4)
C6—C7	1.391 (4)	C27—C28	1.396 (4)
C6—H6	0.9300	C28—C29	1.358 (4)
C7—C8	1.390 (4)	C28—H28	0.9300
C8—C9	1.364 (4)	C29—C30	1.362 (4)
C8—H8	0.9300	C30—C31	1.365 (4)
C9—H9	0.9300	C30—H30	0.9300
C10—C11	1.387 (4)	C31—C32	1.357 (4)
C10—C15	1.391 (4)	C32—H32	0.9300
C11—C12	1.362 (4)	C33—H33A	0.9600
C11—H11	0.9300	C33—H33B	0.9600
C12—C13	1.366 (4)	C33—H33C	0.9600
C13—C14	1.366 (4)	C34—H34A	0.9600
C13—H13	0.9300	C34—H34B	0.9600
C14—C15	1.358 (4)	C34—H34C	0.9600

C5—O2—C16	119.8 (2)	H17A—C17—H17C	109.5
C7—O3—C17	118.9 (2)	H17B—C17—H17C	109.5
C22—O5—C33	119.3 (2)	O4—C18—C19	121.0 (3)
C24—O6—C34	119.0 (2)	O4—C18—C27	118.9 (3)
O1—C1—C2	121.2 (3)	C19—C18—C27	120.1 (2)
O1—C1—C10	119.4 (3)	C20—C19—C18	121.5 (3)
C2—C1—C10	119.4 (2)	C20—C19—H19	119.2
C3—C2—C1	122.7 (3)	C18—C19—H19	119.2
C3—C2—H2	118.6	C19—C20—C21	127.9 (3)
C1—C2—H2	118.6	C19—C20—H20	116.0
C2—C3—C4	128.0 (3)	C21—C20—H20	116.0
C2—C3—H3	116.0	C26—C21—C22	117.2 (2)
C4—C3—H3	116.0	C26—C21—C20	122.7 (3)
C9—C4—C5	116.9 (3)	C22—C21—C20	120.2 (3)
C9—C4—C3	122.9 (3)	O5—C22—C23	123.3 (3)
C5—C4—C3	120.2 (2)	O5—C22—C21	115.6 (2)
O2—C5—C6	122.7 (3)	C23—C22—C21	121.0 (3)
O2—C5—C4	115.8 (2)	C24—C23—C22	119.3 (3)
C6—C5—C4	121.6 (3)	C24—C23—H23	120.3
C7—C6—C5	118.8 (3)	C22—C23—H23	120.3
C7—C6—H6	120.6	O6—C24—C25	115.0 (2)
C5—C6—H6	120.6	O6—C24—C23	124.3 (3)
O3—C7—C8	115.4 (3)	C25—C24—C23	120.7 (3)
O3—C7—C6	124.1 (3)	C26—C25—C24	119.7 (3)
C8—C7—C6	120.5 (3)	C26—C25—H25	120.2
C9—C8—C7	119.8 (3)	C24—C25—H25	120.2
C9—C8—H8	120.1	C25—C26—C21	122.1 (3)
C7—C8—H8	120.1	C25—C26—H26	118.9
C8—C9—C4	122.4 (3)	C21—C26—H26	118.9
C8—C9—H9	118.8	C32—C27—C28	119.0 (3)
C4—C9—H9	118.8	C32—C27—C18	118.4 (3)
C11—C10—C15	119.6 (3)	C28—C27—C18	122.5 (3)
C11—C10—C1	122.6 (3)	C29—C28—C27	118.5 (3)
C15—C10—C1	117.8 (2)	C29—C28—H28	120.7
C12—C11—C10	118.3 (3)	C27—C28—H28	120.7
C12—C11—H11	120.9	C28—C29—F3	118.5 (3)
C10—C11—H11	120.9	C28—C29—C30	123.5 (3)
C11—C12—F1	118.5 (3)	F3—C29—C30	118.0 (3)
C11—C12—C13	123.9 (3)	C29—C30—C31	116.6 (3)
F1—C12—C13	117.6 (3)	C29—C30—H30	121.7
C12—C13—C14	116.0 (3)	C31—C30—H30	121.7
C12—C13—H13	122.0	F4—C31—C32	118.7 (3)
C14—C13—H13	122.0	F4—C31—C30	118.1 (3)
F2—C14—C15	118.3 (3)	C32—C31—C30	123.2 (3)
F2—C14—C13	118.0 (3)	C31—C32—C27	119.1 (3)
C15—C14—C13	123.7 (3)	C31—C32—H32	120.5
C14—C15—C10	118.5 (3)	C27—C32—H32	120.5
C14—C15—H15	120.8	O5—C33—H33A	109.5
C10—C15—H15	120.8	O5—C33—H33B	109.5
O2—C16—H16A	109.5	H33A—C33—H33B	109.5
O2—C16—H16B	109.5	O5—C33—H33C	109.5
H16A—C16—H16B	109.5	H33A—C33—H33C	109.5
O2—C16—H16C	109.5	H33B—C33—H33C	109.5
H16A—C16—H16C	109.5	O6—C34—H34A	109.5
H16B—C16—H16C	109.5	O6—C34—H34B	109.5
O3—C17—H17A	109.5	H34A—C34—H34B	109.5
O3—C17—H17B	109.5	O6—C34—H34C	109.5
H17A—C17—H17B	109.5	H34A—C34—H34C	109.5
O3—C17—H17C	109.5	H34B—C34—H34C	109.5

O1—C1—C2—C3	0.5 (5)	O4—C18—C19—C20	12.7 (5)
C10—C1—C2—C3	179.9 (3)	C27—C18—C19—C20	−165.8 (3)
C1—C2—C3—C4	179.1 (3)	C18—C19—C20—C21	−179.8 (3)
C2—C3—C4—C9	2.3 (5)	C19—C20—C21—C26	8.0 (5)
C2—C3—C4—C5	−178.4 (3)	C19—C20—C21—C22	−172.6 (3)
C16—O2—C5—C6	−6.5 (4)	C33—O5—C22—C23	2.4 (4)
C16—O2—C5—C4	174.0 (3)	C33—O5—C22—C21	−178.5 (2)
C9—C4—C5—O2	178.1 (3)	C26—C21—C22—O5	−178.5 (2)
C3—C4—C5—O2	−1.2 (4)	C20—C21—C22—O5	2.0 (4)
C9—C4—C5—C6	−1.4 (4)	C26—C21—C22—C23	0.6 (4)
C3—C4—C5—C6	179.3 (3)	C20—C21—C22—C23	−178.8 (3)
O2—C5—C6—C7	−179.4 (3)	O5—C22—C23—C24	178.5 (2)
C4—C5—C6—C7	0.1 (4)	C21—C22—C23—C24	−0.6 (4)
C17—O3—C7—C8	175.6 (3)	C34—O6—C24—C25	−178.2 (3)
C17—O3—C7—C6	−4.4 (4)	C34—O6—C24—C23	0.5 (4)
C5—C6—C7—O3	−179.3 (3)	C22—C23—C24—O6	−178.2 (3)
C5—C6—C7—C8	0.7 (4)	C22—C23—C24—C25	0.5 (4)
O3—C7—C8—C9	180.0 (3)	O6—C24—C25—C26	178.5 (3)
C6—C7—C8—C9	0.0 (5)	C23—C24—C25—C26	−0.3 (4)
C7—C8—C9—C4	−1.5 (5)	C24—C25—C26—C21	0.4 (5)
C5—C4—C9—C8	2.1 (4)	C22—C21—C26—C25	−0.5 (4)
C3—C4—C9—C8	−178.6 (3)	C20—C21—C26—C25	178.9 (3)
O1—C1—C10—C11	−175.4 (3)	O4—C18—C27—C32	−1.7 (4)
C2—C1—C10—C11	5.2 (4)	C19—C18—C27—C32	176.7 (3)
O1—C1—C10—C15	5.4 (4)	O4—C18—C27—C28	−178.6 (3)
C2—C1—C10—C15	−174.0 (3)	C19—C18—C27—C28	−0.1 (4)
C15—C10—C11—C12	−0.3 (4)	C32—C27—C28—C29	0.6 (4)
C1—C10—C11—C12	−179.6 (3)	C18—C27—C28—C29	177.4 (3)
C10—C11—C12—F1	−177.0 (2)	C27—C28—C29—F3	−179.8 (3)
C10—C11—C12—C13	0.6 (5)	C27—C28—C29—C30	0.8 (5)
C11—C12—C13—C14	0.3 (5)	C28—C29—C30—C31	−1.7 (5)
F1—C12—C13—C14	177.9 (3)	F3—C29—C30—C31	178.9 (3)
C12—C13—C14—F2	178.3 (3)	C29—C30—C31—F4	−179.2 (3)
C12—C13—C14—C15	−1.5 (5)	C29—C30—C31—C32	1.2 (5)
F2—C14—C15—C10	−178.1 (3)	F4—C31—C32—C27	−179.5 (3)
C13—C14—C15—C10	1.7 (5)	C30—C31—C32—C27	0.1 (5)
C11—C10—C15—C14	−0.7 (4)	C28—C27—C32—C31	−1.0 (5)
C1—C10—C15—C14	178.6 (3)	C18—C27—C32—C31	−177.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C25—H25···F4ⁱ	0.93	2.59	3.375 (3)	142
C13—H13···F4ⁱⁱ	0.93	2.46	3.303 (4)	151
C9—H9···F3ⁱⁱⁱ	0.93	2.66	3.532 (3)	156
C30—H30···F2ⁱⁱ	0.93	2.47	3.303 (4)	149
C8—H8···F2ⁱ	0.93	2.46	3.369 (3)	166
C28—H28···F1ⁱⁱⁱ	0.93	2.53	3.437 (3)	166

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₄F₂O₃
M_r	304.28
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.8047 (8), 11.2591 (12), 17.0080 (18)
α, β, γ (°)	81.407 (2), 81.231 (2), 76.319 (2)
V (Å³)	1425.1 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.27 × 0.22 × 0.17

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.602, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7600, 5242, 2815
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.162, 0.92
No. of reflections	5242
No. of parameters	401
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.20

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C25—H25···F4ⁱ	0.93	2.59	3.375 (3)	142.3
C13—H13···F4ⁱⁱ	0.93	2.46	3.303 (4)	150.5
C9—H9···F3ⁱⁱⁱ	0.93	2.66	3.532 (3)	155.6
C30—H30···F2ⁱⁱ	0.93	2.47	3.303 (4)	149.1
C8—H8···F2ⁱ	0.93	2.46	3.369 (3)	165.6
C28—H28···F1ⁱⁱⁱ	0.93	2.53	3.437 (3)	165.5

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

References

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Volume 66| Part 10| October 2010| Page o2518

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