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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 7| July 2012| Page o1981
https://doi.org/10.1107/S1600536812022490

6-Meth­­oxy­meth­­oxy-7-tri­fluoro­methyl-1,3-benzodioxole-5-carbaldehyde

Yanfeng Wang,a Xinhui Pan,a Dexiu Liub and Hong-Xiang Loua*

aSchool of Pharmaceutical Sciences, Shandong University, Jinan 250012, People's Republic of China, and bShuzhou Health College, Shuzhou 215009, People's Republic of China
*Correspondence e-mail: louhongxiang@sdu.edu.cn

(Received 1 March 2012; accepted 17 May 2012; online 2 June 2012)

The title compound, C11H9F3O5, crystallizes with three mol­ecules in the asymmetric unit. One –CF3 group is disordered by rotation, with the F atoms split over two sets of sites with occupancies which converged to 0.888 (6) and 0.112 (6). Weak π–π inter­actions are observed between adjacent benzene rings [the shortest centroid–centroid distance is 3.8858 (4) Å], resulting in the formation of a supra­molecular chain along [100].

Related literature

For the enhancement of the biological activity of F and CF3 containing mol­ecules compared to their unfluorinated analogues, see: Vrábel et al. (2007[Vrábel, V., Švorc, Ľ., Bradiaková, I., Kožíšek, J. & Krutošíková, A. (2007). Acta Cryst. E63, o4516.]); Wilson & Danishefsky (2010[Wilson, R. M. & Danishefsky, S. J. (2010). Angew. Chem. Int. Ed. 49, 6032-6056.]); Bravo et al. (1994[Bravo, P., Diliddo, D. & Resnati, G. (1994). Tetrahedron, 50, 8827-8836.]); Jung et al. (2002[Jung, J.-C., Watkins, E. B. & Avery, M. A. (2002). Tetrahedron, 58, 3639-3646.]). For the synthesis of the title compound, an inter­mediate for the synthesis of biologic­ally active compounds, see: Corey et al. (1996[Corey, E. J., Gin, D. Y. & Kania, R. S. (1996). J. Am. Chem. Soc. 118, 9202-9203.]); Weeratunga et al. (1987[Weeratunga, G., Jaworska-Sobiesiak, A., Horne, S. & Rodrigo, R. (1987). Can. J. Chem. 65, 2019-2023.]); Wu et al. (2004[Wu, T. R., Shen, L. & Chong, J. M. (2004). Org. Lett. 6, 2701-2704.]).

[Scheme 1]

Experimental

Crystal data

  • C11H9F3O5

  • Mr = 278.18

  • Triclinic, [P \overline 1]

  • a = 9.3608 (10) Å

  • b = 12.6895 (14) Å

  • c = 14.6765 (16) Å

  • α = 97.007 (2)°

  • β = 93.625 (2)°

  • γ = 102.983 (2)°

  • V = 1678.7 (3) Å3

  • Z = 6

  • Mo Kα radiation

  • μ = 0.16 mm−1

  • T = 173 K

  • 0.10 × 0.10 × 0.10 mm
Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.984, Tmax = 0.984

  • 8355 measured reflections

  • 5842 independent reflections

  • 4928 reflections with I > 2σ(I)

  • Rint = 0.021
Refinement

  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 0.122

  • S = 1.03

  • 5842 reflections

  • 545 parameters

  • 18 restraints

  • H-atom parameters constrained

  • Δρmax = 0.28 e Å−3

  • Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. 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: DIAMOND (Brandenburg, 2008[Brandenburg, K. (2008). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812022490/bh2420sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812022490/bh2420Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812022490/bh2420Isup3.cml

checkCIF report


Comment top

In recent years, fluorinated compounds have been very important in the pharmaceutical field. Incorporation of a F atom instead of an H atom can alter the biological activity of a compound. Introduction of further F atoms in a CF3 group provides better lipophilicity, and the compounds might be pharmacologically more interesting compared to their non-fluorinated analogues (Vrábel et al., 2007). Many heterocyclic compounds, which bear the trifluoromethyl group, are far superior to the parent compounds regarding their biological activity (Wilson & Danishefsky, 2010), including herbicides (Bravo et al., 1994) and fungicides (Jung et al., 2002). We report here the crystal structure of the title compound, which is used as an important starting material for the synthesis of a natural product derivative.

Related literature top

For the enhancement of the biological activity of F and CF3 containing molecules compared to their unfluorinated analogues, see: Vrábel et al. (2007); Wilson & Danishefsky (2010); Bravo et al. (1994); Jung et al. (2002). For the synthesis of the title compound, an intermediate for the synthesis of biologically active compounds, see: Corey et al. (1996); Weeratunga et al. (1987); Wu et al. (2004).

Experimental top

The title compound was synthesized according to literature methods (Corey et al., 1996; Wu et al., 2004; Weeratunga et al., 1987). The resulting product was purified by column chromatography (silica gel, 200–300 meshes, eluent petroleum ether/ethyl acetate 10:1). The solid residue was crystallized by slow evaporation of an hexane/ethyl acetate (5:1) solution at room temperature. 1H-NMR (600 MHz, CDCl3) δ 3.62 (s, 3H, OCH3), 5.09 (s, 2H, CH2), 6.16 (s, 2H, ArOCH2), 7.42 (s, 1H, ArH), 10.14 (s, 1H, CHO); 13C-NMR (150 MHz, CDCl3) δ 58.11, 102, 103, 108, 123, 125, 145, 151, 155, 188; HRMS (EI+) m/z: calcd. for C11H9F3O5 (M+): 279.19, found: 279.19.

Refinement top

All H atoms were placed geometrically and treated as riding on their parent atoms with C—H = 0.98 (methyl), 0.95 (aromatic) or 0.99 Å (methylene), and Uiso(H) = x Ueq(C), with x = 1.5 for methyl groups and 1.2 for other H atoms. The CF3 group is disordered by rotation, and the F atoms are split over two sets of sites with occupancies of 0.888 (6) and 0.112 (6). Restraints were applied on these atoms.

Structure description top

In recent years, fluorinated compounds have been very important in the pharmaceutical field. Incorporation of a F atom instead of an H atom can alter the biological activity of a compound. Introduction of further F atoms in a CF3 group provides better lipophilicity, and the compounds might be pharmacologically more interesting compared to their non-fluorinated analogues (Vrábel et al., 2007). Many heterocyclic compounds, which bear the trifluoromethyl group, are far superior to the parent compounds regarding their biological activity (Wilson & Danishefsky, 2010), including herbicides (Bravo et al., 1994) and fungicides (Jung et al., 2002). We report here the crystal structure of the title compound, which is used as an important starting material for the synthesis of a natural product derivative.

For the enhancement of the biological activity of F and CF3 containing molecules compared to their unfluorinated analogues, see: Vrábel et al. (2007); Wilson & Danishefsky (2010); Bravo et al. (1994); Jung et al. (2002). For the synthesis of the title compound, an intermediate for the synthesis of biologically active compounds, see: Corey et al. (1996); Weeratunga et al. (1987); Wu et al. (2004).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The asymmetric unit view of the title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii.
6-Methoxymethoxy-7-trifluoromethyl-1,3-benzodioxole-5-carbaldehyde top
Crystal data top
C11H9F3O5Z = 6
Mr = 278.18F(000) = 852
Triclinic, P1Dx = 1.651 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.3608 (10) ÅCell parameters from 4637 reflections
b = 12.6895 (14) Åθ = 2.8–27.5°
c = 14.6765 (16) ŵ = 0.16 mm−1
α = 97.007 (2)°T = 173 K
β = 93.625 (2)°Block, colourless
γ = 102.983 (2)°0.10 × 0.10 × 0.10 mm
V = 1678.7 (3) Å3
Data collection top
Bruker APEXII CCD
diffractometer		5842 independent reflections
Radiation source: fine-focus sealed tube4928 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
φ and ω scansθmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		h = −10→11
Tmin = 0.984, Tmax = 0.984k = −15→10
8355 measured reflectionsl = −17→16
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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0634P)2 + 0.6455P]
where P = (Fo2 + 2Fc2)/3
5842 reflections(Δ/σ)max = 0.002
545 parametersΔρmax = 0.28 e Å−3
18 restraintsΔρmin = −0.28 e Å−3
0 constraints
Crystal data top
C11H9F3O5γ = 102.983 (2)°
Mr = 278.18V = 1678.7 (3) Å3
Triclinic, P1Z = 6
a = 9.3608 (10) ÅMo Kα radiation
b = 12.6895 (14) ŵ = 0.16 mm−1
c = 14.6765 (16) ÅT = 173 K
α = 97.007 (2)°0.10 × 0.10 × 0.10 mm
β = 93.625 (2)°
Data collection top
Bruker APEXII CCD
diffractometer		5842 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		4928 reflections with I > 2σ(I)
Tmin = 0.984, Tmax = 0.984Rint = 0.021
8355 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04118 restraints
wR(F2) = 0.122H-atom parameters constrained
S = 1.03Δρmax = 0.28 e Å−3
5842 reflectionsΔρmin = −0.28 e Å−3
545 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.4148 (2)0.44220 (14)0.24627 (12)0.0258 (4)
C20.5685 (2)0.46616 (14)0.26506 (12)0.0259 (4)
C30.6377 (2)0.50456 (16)0.36188 (13)0.0322 (4)
C40.6498 (2)0.45487 (14)0.19079 (12)0.0255 (4)
C50.8251 (2)0.46037 (18)0.09341 (13)0.0340 (4)
H5A0.86850.53240.07510.041*
H5B0.89440.41260.08250.041*
C60.5815 (2)0.41995 (14)0.10140 (12)0.0253 (4)
C70.4337 (2)0.39694 (14)0.08251 (12)0.0254 (4)
H70.38940.37320.02120.030*
C80.3471 (2)0.40933 (14)0.15670 (12)0.0261 (4)
C90.1878 (2)0.39213 (16)0.13658 (13)0.0325 (4)
H90.13110.40920.18540.039*
C100.2684 (2)0.36310 (17)0.36009 (14)0.0368 (5)
H10A0.31650.30320.34050.044*
H10B0.28490.38010.42810.044*
C110.0396 (3)0.4048 (2)0.3714 (2)0.0561 (7)
H11A−0.06590.37440.35460.084*
H11B0.07010.47370.34630.084*
H11C0.05910.41830.43870.084*
C120.4460 (2)0.79048 (15)0.33160 (12)0.0260 (4)
C130.6003 (2)0.82136 (15)0.34819 (12)0.0278 (4)
C140.6724 (2)0.88593 (18)0.43803 (14)0.0377 (5)
C150.6789 (2)0.78481 (15)0.27987 (12)0.0261 (4)
C160.8521 (2)0.74583 (17)0.19183 (14)0.0350 (5)
H16A0.90850.79910.15570.042*
H16B0.90930.69070.20180.042*
C170.6090 (2)0.72025 (14)0.19871 (12)0.0242 (4)
C180.4606 (2)0.69090 (14)0.18152 (12)0.0257 (4)
H180.41490.64710.12560.031*
C190.3766 (2)0.72763 (14)0.24954 (12)0.0253 (4)
C200.2158 (2)0.70242 (17)0.23068 (13)0.0327 (4)
H200.16150.73870.27130.039*
C210.3062 (3)0.7483 (2)0.45855 (15)0.0446 (6)
H21A0.36020.68940.45460.054*
H21B0.32140.78510.52300.054*
C220.0704 (3)0.7777 (2)0.4588 (2)0.0585 (7)
H22A−0.03360.74050.44400.088*
H22B0.09470.83900.42340.088*
H22C0.08870.80520.52480.088*
C230.5757 (2)0.86851 (15)0.85712 (13)0.0308 (4)
C240.4215 (2)0.85065 (15)0.84339 (13)0.0306 (4)
C250.3445 (3)0.84013 (18)0.74898 (14)0.0396 (5)
C260.3451 (2)0.84472 (14)0.92068 (13)0.0281 (4)
C270.1749 (2)0.82327 (18)1.02165 (13)0.0353 (5)
H27A0.11540.87521.04310.042*
H27B0.12200.74881.03020.042*
C280.4178 (2)0.85820 (14)1.00856 (12)0.0263 (4)
C290.5655 (2)0.87629 (14)1.02279 (13)0.0282 (4)
H290.61320.88621.08340.034*
C300.6474 (2)0.88013 (15)0.94515 (13)0.0300 (4)
C310.8066 (2)0.89239 (17)0.96167 (17)0.0410 (5)
H310.86160.88530.90990.049*
C320.7103 (3)0.97212 (17)0.75019 (14)0.0423 (5)
H32A0.70490.96270.68200.051*
H32B0.64871.02320.77020.051*
C330.9564 (3)0.9601 (2)0.7452 (2)0.0651 (8)
H33A1.05510.99170.77660.098*
H33B0.95730.96800.67960.098*
H33C0.92710.88250.75190.098*
F10.78370 (14)0.52599 (14)0.36687 (9)0.0609 (4)
F20.59564 (16)0.43130 (10)0.41881 (8)0.0491 (3)
F30.60334 (15)0.59570 (9)0.39913 (8)0.0439 (3)
F40.63938 (19)0.83087 (13)0.50907 (9)0.0677 (5)
F50.81807 (15)0.91193 (15)0.44024 (11)0.0737 (5)
F60.63210 (16)0.97844 (11)0.45818 (9)0.0548 (4)
F70.3831 (3)0.93019 (15)0.71022 (16)0.0706 (9)0.888 (6)
F7B0.302 (3)0.9299 (16)0.7436 (13)0.074 (6)0.112 (6)
F80.3705 (3)0.7592 (2)0.69059 (10)0.0583 (7)0.888 (6)
F8B0.431 (2)0.827 (2)0.6842 (10)0.067 (5)0.112 (6)
F90.1981 (2)0.8201 (3)0.74828 (13)0.0635 (7)0.888 (6)
F9B0.231 (2)0.7631 (17)0.7437 (11)0.059 (5)0.112 (6)
O10.79772 (14)0.47249 (11)0.18950 (9)0.0330 (3)
O20.68690 (14)0.41280 (11)0.04150 (9)0.0324 (3)
O30.12449 (15)0.35701 (13)0.06032 (10)0.0409 (4)
O40.33447 (15)0.45868 (11)0.31963 (9)0.0315 (3)
O50.12040 (16)0.32932 (12)0.33439 (10)0.0430 (4)
O60.82681 (14)0.80063 (12)0.27905 (9)0.0368 (3)
O70.71247 (14)0.69427 (11)0.14359 (9)0.0320 (3)
O80.14850 (15)0.63790 (12)0.16616 (10)0.0402 (4)
O90.36529 (15)0.82610 (11)0.39864 (9)0.0332 (3)
O100.15914 (18)0.70333 (13)0.43583 (11)0.0484 (4)
O110.19842 (15)0.82781 (12)0.92587 (9)0.0376 (3)
O120.31665 (14)0.85179 (11)1.07222 (9)0.0321 (3)
O130.87177 (16)0.91108 (14)1.03801 (12)0.0492 (4)
O140.65266 (17)0.86765 (11)0.78023 (10)0.0403 (4)
O150.85359 (18)1.01619 (12)0.78551 (11)0.0475 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0318 (10)0.0228 (9)0.0231 (9)0.0070 (7)0.0041 (7)0.0030 (7)
C20.0323 (10)0.0223 (9)0.0223 (9)0.0061 (7)−0.0012 (7)0.0028 (7)
C30.0376 (11)0.0331 (10)0.0251 (10)0.0095 (9)−0.0019 (8)0.0012 (8)
C40.0261 (9)0.0228 (9)0.0270 (9)0.0049 (7)−0.0013 (7)0.0040 (7)
C50.0247 (10)0.0436 (12)0.0313 (10)0.0075 (9)0.0026 (8)−0.0035 (9)
C60.0287 (10)0.0223 (9)0.0237 (9)0.0041 (7)0.0028 (7)0.0018 (7)
C70.0296 (10)0.0237 (9)0.0208 (9)0.0040 (7)−0.0016 (7)0.0010 (7)
C80.0269 (10)0.0233 (9)0.0266 (9)0.0032 (7)0.0006 (7)0.0037 (7)
C90.0303 (10)0.0374 (11)0.0290 (10)0.0057 (8)0.0030 (8)0.0060 (8)
C100.0416 (12)0.0398 (11)0.0304 (10)0.0076 (9)0.0090 (9)0.0113 (9)
C110.0421 (14)0.0574 (15)0.0715 (17)0.0114 (12)0.0225 (12)0.0110 (13)
C120.0320 (10)0.0260 (9)0.0216 (9)0.0095 (8)0.0053 (7)0.0037 (7)
C130.0333 (10)0.0260 (9)0.0229 (9)0.0066 (8)−0.0004 (8)0.0012 (7)
C140.0393 (12)0.0420 (12)0.0280 (10)0.0080 (9)−0.0018 (9)−0.0049 (9)
C150.0258 (9)0.0259 (9)0.0257 (9)0.0040 (7)0.0004 (7)0.0049 (7)
C160.0259 (10)0.0394 (11)0.0363 (11)0.0050 (8)0.0046 (8)−0.0034 (9)
C170.0291 (10)0.0234 (9)0.0203 (9)0.0055 (7)0.0047 (7)0.0036 (7)
C180.0293 (10)0.0244 (9)0.0219 (9)0.0039 (7)−0.0008 (7)0.0029 (7)
C190.0264 (9)0.0266 (9)0.0234 (9)0.0058 (7)0.0024 (7)0.0061 (7)
C200.0291 (10)0.0427 (11)0.0270 (10)0.0087 (9)0.0045 (8)0.0059 (9)
C210.0489 (14)0.0646 (15)0.0299 (11)0.0241 (12)0.0136 (10)0.0188 (10)
C220.0427 (14)0.0707 (18)0.0671 (17)0.0150 (13)0.0168 (12)0.0199 (14)
C230.0410 (11)0.0205 (9)0.0317 (10)0.0068 (8)0.0114 (8)0.0032 (8)
C240.0410 (11)0.0240 (9)0.0263 (10)0.0075 (8)0.0019 (8)0.0023 (7)
C250.0499 (14)0.0379 (12)0.0304 (11)0.0103 (10)0.0011 (10)0.0043 (9)
C260.0305 (10)0.0224 (9)0.0310 (10)0.0064 (7)0.0004 (8)0.0033 (7)
C270.0286 (10)0.0443 (12)0.0326 (10)0.0080 (9)0.0039 (8)0.0044 (9)
C280.0310 (10)0.0208 (9)0.0268 (9)0.0049 (7)0.0036 (8)0.0037 (7)
C290.0322 (10)0.0222 (9)0.0293 (10)0.0044 (8)−0.0004 (8)0.0058 (7)
C300.0325 (10)0.0214 (9)0.0362 (11)0.0048 (8)0.0055 (8)0.0060 (8)
C310.0351 (11)0.0374 (12)0.0532 (14)0.0076 (9)0.0125 (10)0.0149 (10)
C320.0579 (14)0.0348 (11)0.0305 (11)0.0005 (10)0.0124 (10)0.0057 (9)
C330.0581 (16)0.0467 (14)0.086 (2)0.0018 (12)0.0384 (15)−0.0041 (14)
F10.0348 (7)0.1043 (12)0.0347 (7)0.0138 (7)−0.0097 (6)−0.0128 (7)
F20.0797 (10)0.0418 (7)0.0255 (6)0.0151 (7)−0.0074 (6)0.0086 (5)
F30.0665 (9)0.0327 (6)0.0298 (6)0.0150 (6)−0.0069 (6)−0.0059 (5)
F40.1021 (12)0.0654 (10)0.0266 (7)0.0079 (9)−0.0151 (7)0.0041 (6)
F50.0385 (8)0.1045 (13)0.0585 (9)0.0084 (8)−0.0117 (7)−0.0416 (9)
F60.0660 (9)0.0422 (7)0.0490 (8)0.0134 (7)−0.0026 (7)−0.0187 (6)
F70.100 (2)0.0513 (11)0.0553 (13)0.0039 (11)−0.0237 (12)0.0275 (9)
F7B0.090 (10)0.087 (9)0.060 (8)0.041 (8)0.001 (7)0.027 (7)
F80.0898 (16)0.0586 (14)0.0277 (8)0.0307 (12)−0.0052 (8)−0.0091 (8)
F8B0.071 (8)0.080 (10)0.044 (7)0.015 (7)−0.002 (6)−0.001 (6)
F90.0491 (11)0.102 (2)0.0359 (9)0.0194 (12)−0.0100 (7)−0.0001 (11)
F9B0.042 (7)0.065 (9)0.056 (7)−0.011 (6)−0.016 (6)0.012 (7)
O10.0248 (7)0.0443 (8)0.0283 (7)0.0074 (6)−0.0019 (5)0.0019 (6)
O20.0266 (7)0.0425 (8)0.0255 (7)0.0059 (6)0.0037 (5)−0.0018 (6)
O30.0273 (7)0.0540 (9)0.0351 (8)0.0020 (7)−0.0033 (6)−0.0017 (7)
O40.0358 (7)0.0327 (7)0.0260 (7)0.0067 (6)0.0094 (6)0.0026 (5)
O50.0402 (9)0.0381 (8)0.0459 (9)0.0005 (7)0.0076 (7)0.0018 (7)
O60.0254 (7)0.0481 (9)0.0310 (7)0.0023 (6)0.0004 (6)−0.0042 (6)
O70.0250 (7)0.0414 (8)0.0275 (7)0.0067 (6)0.0041 (5)−0.0026 (6)
O80.0291 (7)0.0477 (9)0.0380 (8)0.0017 (6)−0.0017 (6)−0.0002 (7)
O90.0367 (8)0.0392 (8)0.0259 (7)0.0136 (6)0.0089 (6)0.0018 (6)
O100.0526 (10)0.0443 (9)0.0478 (9)0.0061 (7)0.0148 (8)0.0091 (7)
O110.0298 (7)0.0524 (9)0.0307 (7)0.0103 (6)−0.0004 (6)0.0070 (6)
O120.0287 (7)0.0409 (8)0.0264 (7)0.0072 (6)0.0041 (5)0.0044 (6)
O130.0317 (8)0.0565 (10)0.0582 (11)0.0059 (7)−0.0002 (7)0.0138 (8)
O140.0552 (9)0.0282 (7)0.0364 (8)0.0045 (6)0.0207 (7)0.0017 (6)
O150.0506 (10)0.0347 (8)0.0508 (9)−0.0011 (7)0.0165 (8)−0.0044 (7)
Geometric parameters (Å, º) top
C1—O41.373 (2)C18—C191.408 (3)
C1—C81.395 (3)C18—H180.9500
C1—C21.404 (3)C19—C201.467 (3)
C2—C41.380 (3)C20—O81.212 (2)
C2—C31.500 (2)C20—H200.9500
C3—F11.327 (2)C21—O101.369 (3)
C3—F31.332 (2)C21—O91.443 (2)
C3—F21.336 (2)C21—H21A0.9900
C4—O11.354 (2)C21—H21B0.9900
C4—C61.397 (3)C22—O101.416 (3)
C5—O21.425 (2)C22—H22A0.9800
C5—O11.445 (2)C22—H22B0.9800
C5—H5A0.9900C22—H22C0.9800
C5—H5B0.9900C23—O141.377 (2)
C6—C71.352 (3)C23—C301.393 (3)
C6—O21.373 (2)C23—C241.407 (3)
C7—C81.412 (3)C24—C261.379 (3)
C7—H70.9500C24—C251.497 (3)
C8—C91.464 (3)C25—F9B1.266 (15)
C9—O31.216 (2)C25—F8B1.304 (16)
C9—H90.9500C25—F7B1.300 (18)
C10—O51.368 (2)C25—F71.326 (3)
C10—O41.446 (2)C25—F91.336 (3)
C10—H10A0.9900C25—F81.331 (3)
C10—H10B0.9900C26—O111.350 (2)
C11—O51.427 (3)C26—C281.392 (3)
C11—H11A0.9800C27—O121.427 (2)
C11—H11B0.9800C27—O111.443 (2)
C11—H11C0.9800C27—H27A0.9900
C12—O91.372 (2)C27—H27B0.9900
C12—C191.394 (3)C28—C291.348 (3)
C12—C131.406 (3)C28—O121.368 (2)
C13—C151.377 (3)C29—C301.413 (3)
C13—C141.497 (3)C29—H290.9500
C14—F61.318 (3)C30—C311.465 (3)
C14—F51.326 (3)C31—O131.211 (3)
C14—F41.339 (3)C31—H310.9500
C15—O61.355 (2)C32—O151.373 (3)
C15—C171.393 (3)C32—O141.447 (2)
C16—O71.422 (2)C32—H32A0.9900
C16—O61.440 (2)C32—H32B0.9900
C16—H16A0.9900C33—O151.435 (3)
C16—H16B0.9900C33—H33A0.9800
C17—C181.353 (3)C33—H33B0.9800
C17—O71.371 (2)C33—H33C0.9800
O4—C1—C8121.40 (16)O8—C20—C19123.64 (18)
O4—C1—C2116.80 (15)O8—C20—H20118.2
C8—C1—C2121.70 (16)C19—C20—H20118.2
C4—C2—C1116.89 (16)O10—C21—O9112.04 (17)
C4—C2—C3122.85 (17)O10—C21—H21A109.2
C1—C2—C3120.25 (16)O9—C21—H21A109.2
F1—C3—F3106.24 (16)O10—C21—H21B109.2
F1—C3—F2106.72 (16)O9—C21—H21B109.2
F3—C3—F2105.70 (16)H21A—C21—H21B107.9
F1—C3—C2112.31 (16)O10—C22—H22A109.5
F3—C3—C2112.74 (16)O10—C22—H22B109.5
F2—C3—C2112.61 (16)H22A—C22—H22B109.5
O1—C4—C2128.95 (16)O10—C22—H22C109.5
O1—C4—C6109.80 (16)H22A—C22—H22C109.5
C2—C4—C6121.24 (17)H22B—C22—H22C109.5
O2—C5—O1107.09 (14)O14—C23—C30120.96 (18)
O2—C5—H5A110.3O14—C23—C24117.75 (17)
O1—C5—H5A110.3C30—C23—C24121.18 (17)
O2—C5—H5B110.3C26—C24—C23117.07 (17)
O1—C5—H5B110.3C26—C24—C25121.70 (18)
H5A—C5—H5B108.6C23—C24—C25121.22 (18)
C7—C6—O2128.38 (16)F9B—C25—F8B113.5 (12)
C7—C6—C4122.35 (17)F9B—C25—F7B107.7 (12)
O2—C6—C4109.26 (16)F8B—C25—F7B109.0 (12)
C6—C7—C8117.95 (16)F7—C25—F9105.5 (2)
C6—C7—H7121.0F7—C25—F8106.5 (2)
C8—C7—H7121.0F9—C25—F8105.2 (2)
C1—C8—C7119.84 (17)F7—C25—C24112.52 (18)
C1—C8—C9121.52 (17)F9—C25—C24113.25 (18)
C7—C8—C9118.57 (16)F8—C25—C24113.20 (18)
O3—C9—C8123.04 (18)O11—C26—C24128.49 (17)
O3—C9—H9118.5O11—C26—C28110.13 (16)
C8—C9—H9118.5C24—C26—C28121.38 (18)
O5—C10—O4111.60 (16)O12—C27—O11106.96 (15)
O5—C10—H10A109.3O12—C27—H27A110.3
O4—C10—H10A109.3O11—C27—H27A110.3
O5—C10—H10B109.3O12—C27—H27B110.3
O4—C10—H10B109.3O11—C27—H27B110.3
H10A—C10—H10B108.0H27A—C27—H27B108.6
O5—C11—H11A109.5C29—C28—O12128.65 (17)
O5—C11—H11B109.5C29—C28—C26122.17 (17)
H11A—C11—H11B109.5O12—C28—C26109.17 (16)
O5—C11—H11C109.5C28—C29—C30118.16 (17)
H11A—C11—H11C109.5C28—C29—H29120.9
H11B—C11—H11C109.5C30—C29—H29120.9
O9—C12—C19120.80 (16)C23—C30—C29120.00 (18)
O9—C12—C13117.59 (16)C23—C30—C31122.72 (18)
C19—C12—C13121.61 (16)C29—C30—C31117.23 (18)
C15—C13—C12116.53 (16)O13—C31—C30123.3 (2)
C15—C13—C14122.72 (17)O13—C31—H31118.4
C12—C13—C14120.69 (17)C30—C31—H31118.4
F6—C14—F5106.30 (18)O15—C32—O14111.72 (18)
F6—C14—F4105.33 (17)O15—C32—H32A109.3
F5—C14—F4106.69 (18)O14—C32—H32A109.3
F6—C14—C13113.57 (17)O15—C32—H32B109.3
F5—C14—C13112.56 (17)O14—C32—H32B109.3
F4—C14—C13111.84 (17)H32A—C32—H32B107.9
O6—C15—C13128.50 (16)O15—C33—H33A109.5
O6—C15—C17109.80 (16)O15—C33—H33B109.5
C13—C15—C17121.68 (17)H33A—C33—H33B109.5
O7—C16—O6107.78 (15)O15—C33—H33C109.5
O7—C16—H16A110.2H33A—C33—H33C109.5
O6—C16—H16A110.2H33B—C33—H33C109.5
O7—C16—H16B110.2C4—O1—C5106.13 (13)
O6—C16—H16B110.2C6—O2—C5106.07 (14)
H16A—C16—H16B108.5C1—O4—C10116.60 (14)
C18—C17—O7128.01 (16)C10—O5—C11112.88 (17)
C18—C17—C15122.36 (17)C15—O6—C16106.43 (14)
O7—C17—C15109.63 (15)C17—O7—C16106.33 (14)
C17—C18—C19117.56 (16)C12—O9—C21116.13 (15)
C17—C18—H18121.2C21—O10—C22112.81 (19)
C19—C18—H18121.2C26—O11—C27106.53 (14)
C12—C19—C18120.25 (16)C28—O12—C27106.64 (14)
C12—C19—C20120.90 (17)C23—O14—C32116.82 (15)
C18—C19—C20118.80 (16)C32—O15—C33113.45 (18)
O4—C1—C2—C4−176.86 (15)C26—C24—C25—F9B−42.5 (13)
C8—C1—C2—C4−0.5 (3)C23—C24—C25—F9B138.4 (12)
O4—C1—C2—C31.8 (2)C26—C24—C25—F8B−167.6 (12)
C8—C1—C2—C3178.13 (16)C23—C24—C25—F8B13.2 (12)
C4—C2—C3—F10.1 (3)C26—C24—C25—F7B72.8 (13)
C1—C2—C3—F1−178.42 (17)C23—C24—C25—F7B−106.4 (13)
C4—C2—C3—F3120.10 (19)C26—C24—C25—F7116.7 (3)
C1—C2—C3—F3−58.4 (2)C23—C24—C25—F7−62.4 (3)
C4—C2—C3—F2−120.39 (19)C26—C24—C25—F9−2.8 (3)
C1—C2—C3—F261.1 (2)C23—C24—C25—F9178.0 (2)
C1—C2—C4—O1179.94 (17)C26—C24—C25—F8−122.5 (2)
C3—C2—C4—O11.4 (3)C23—C24—C25—F858.3 (3)
C1—C2—C4—C6−0.7 (3)C23—C24—C26—O11−179.62 (17)
C3—C2—C4—C6−179.32 (17)C25—C24—C26—O111.2 (3)
O1—C4—C6—C7−179.61 (16)C23—C24—C26—C281.4 (3)
C2—C4—C6—C70.9 (3)C25—C24—C26—C28−177.84 (17)
O1—C4—C6—O21.2 (2)O11—C26—C28—C29179.98 (16)
C2—C4—C6—O2−178.25 (16)C24—C26—C28—C29−0.8 (3)
O2—C6—C7—C8179.14 (17)O11—C26—C28—O12−1.0 (2)
C4—C6—C7—C80.1 (3)C24—C26—C28—O12178.14 (16)
O4—C1—C8—C7177.74 (16)O12—C28—C29—C30−179.55 (17)
C2—C1—C8—C71.5 (3)C26—C28—C29—C30−0.8 (3)
O4—C1—C8—C90.7 (3)O14—C23—C30—C29−177.40 (16)
C2—C1—C8—C9−175.48 (17)C24—C23—C30—C29−1.3 (3)
C6—C7—C8—C1−1.3 (3)O14—C23—C30—C310.2 (3)
C6—C7—C8—C9175.79 (16)C24—C23—C30—C31176.32 (17)
C1—C8—C9—O3−175.27 (18)C28—C29—C30—C231.8 (3)
C7—C8—C9—O37.7 (3)C28—C29—C30—C31−175.92 (17)
O9—C12—C13—C15−179.89 (15)C23—C30—C31—O13174.0 (2)
C19—C12—C13—C15−1.0 (3)C29—C30—C31—O13−8.3 (3)
O9—C12—C13—C143.1 (3)C2—C4—O1—C5−173.78 (18)
C19—C12—C13—C14−178.07 (17)C6—C4—O1—C56.8 (2)
C15—C13—C14—F6126.8 (2)O2—C5—O1—C4−12.1 (2)
C12—C13—C14—F6−56.4 (3)C7—C6—O2—C5172.08 (18)
C15—C13—C14—F55.9 (3)C4—C6—O2—C5−8.79 (19)
C12—C13—C14—F5−177.21 (18)O1—C5—O2—C612.8 (2)
C15—C13—C14—F4−114.2 (2)C8—C1—O4—C1083.8 (2)
C12—C13—C14—F462.7 (2)C2—C1—O4—C10−99.78 (19)
C12—C13—C15—O6−178.52 (17)O5—C10—O4—C1−103.73 (19)
C14—C13—C15—O6−1.5 (3)O4—C10—O5—C11−67.4 (2)
C12—C13—C15—C17−0.2 (3)C13—C15—O6—C16−179.92 (19)
C14—C13—C15—C17176.76 (18)C17—C15—O6—C161.6 (2)
O6—C15—C17—C18179.50 (16)O7—C16—O6—C15−2.1 (2)
C13—C15—C17—C180.9 (3)C18—C17—O7—C16179.16 (18)
O6—C15—C17—O7−0.6 (2)C15—C17—O7—C16−0.75 (19)
C13—C15—C17—O7−179.15 (16)O6—C16—O7—C171.7 (2)
O7—C17—C18—C19179.76 (16)C19—C12—O9—C2181.4 (2)
C15—C17—C18—C19−0.3 (3)C13—C12—O9—C21−99.8 (2)
O9—C12—C19—C18−179.54 (15)O10—C21—O9—C12−102.7 (2)
C13—C12—C19—C181.6 (3)O9—C21—O10—C22−71.9 (2)
O9—C12—C19—C203.1 (3)C24—C26—O11—C27177.13 (19)
C13—C12—C19—C20−175.78 (17)C28—C26—O11—C27−3.8 (2)
C17—C18—C19—C12−0.9 (3)O12—C27—O11—C267.0 (2)
C17—C18—C19—C20176.55 (16)C29—C28—O12—C27−175.68 (19)
C12—C19—C20—O8−170.82 (18)C26—C28—O12—C275.4 (2)
C18—C19—C20—O811.7 (3)O11—C27—O12—C28−7.6 (2)
O14—C23—C24—C26175.93 (16)C30—C23—O14—C32−89.6 (2)
C30—C23—C24—C26−0.3 (3)C24—C23—O14—C3294.2 (2)
O14—C23—C24—C25−4.9 (3)O15—C32—O14—C2394.5 (2)
C30—C23—C24—C25178.90 (17)O14—C32—O15—C3371.4 (2)

Experimental details

Crystal data
Chemical formulaC11H9F3O5
Mr278.18
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)9.3608 (10), 12.6895 (14), 14.6765 (16)
α, β, γ (°)97.007 (2), 93.625 (2), 102.983 (2)
V (Å3)1678.7 (3)
Z6
Radiation typeMo Kα
µ (mm−1)0.16
Crystal size (mm)0.10 × 0.10 × 0.10
Data collection
DiffractometerBruker APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.984, 0.984
No. of measured, independent and
observed [I > 2σ(I)] reflections		8355, 5842, 4928
Rint0.021
(sin θ/λ)max (Å−1)0.594
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.122, 1.03
No. of reflections5842
No. of parameters545
No. of restraints18
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.28, −0.28

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2008), publCIF (Westrip, 2010).

 

Acknowledgements

The data were collected at the School of Chemistry and Chemical Engineering, Shandong University. This work was supported financially by the Shandong Provincial Doctoral Foundation, China (grant No. 21310004021142).

References

First citationBrandenburg, K. (2008). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
 First citationBravo, P., Diliddo, D. & Resnati, G. (1994). Tetrahedron, 50, 8827–8836.  CrossRef CAS Web of Science Google Scholar
 First citationBruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationCorey, E. J., Gin, D. Y. & Kania, R. S. (1996). J. Am. Chem. Soc. 118, 9202–9203.  CrossRef CAS Web of Science Google Scholar
 First citationJung, J.-C., Watkins, E. B. & Avery, M. A. (2002). Tetrahedron, 58, 3639–3646.  Web of Science CrossRef CAS Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
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 First citationWeeratunga, G., Jaworska-Sobiesiak, A., Horne, S. & Rodrigo, R. (1987). Can. J. Chem. 65, 2019–2023.  CrossRef CAS Web of Science Google Scholar
 First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationWilson, R. M. & Danishefsky, S. J. (2010). Angew. Chem. Int. Ed. 49, 6032–6056.  Web of Science CrossRef CAS Google Scholar
 First citationWu, T. R., Shen, L. & Chong, J. M. (2004). Org. Lett. 6, 2701–2704.  Web of Science CrossRef PubMed CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 68| Part 7| July 2012| Page o1981
https://doi.org/10.1107/S1600536812022490
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