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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 5| May 2011| Page o1054

A new polymorph of 2,6-bis­­(tri­fluoro­meth­yl)benzoic acid

aThe Maritimes Centre for Green Chemistry and the Department of Chemistry, Saint Mary's University, 923 Robie Street, Halifax, NS B3H 3C3, Canada
*Correspondence e-mail: jason.masuda@smu.ca

(Received 24 March 2011; accepted 29 March 2011; online 7 April 2011)

The asymmetric unit of a second polymorph of the title compound, C9H4F6O2, contains five independent mol­ecules, which form hydrogen-bonded O—H⋯O dimers about inversion centers. The most significant structural difference between this structure and that of the first polymorph [Tobin & Masuda (2009[Tobin, J. M. & Masuda, J. D. (2009). Acta Cryst. E65, o1217.]). Acta Cryst. E65, o1217] is the hydrogen-bonded, dimeric orientation of the carb­oxy­lic acid functionalities.

Related literature

For the first polymorph of the title compound, see: Tobin & Masuda (2009[Tobin, J. M. & Masuda, J. D. (2009). Acta Cryst. E65, o1217.]). For details of the synthesis, see: Dmowski & Piasecka-Macieiewska (1998)[Dmowski, W. & Piasecka-Macieiewska, K. (1998). Tetrahedron, 54, 6781-6792.]. For information on dimeric versus catemeric crystal growth in benzoic acids, see: Moorthy et al. (2002[Moorthy, J. N., Natarajan, R., Mal, P. & Venugopalan, P. (2002). J. Am. Chem. Soc. 124, 6530-6531.]).

[Scheme 1]

Experimental

Crystal data
  • C9H4F6O2

  • Mr = 258.12

  • Triclinic, [P \overline 1]

  • a = 10.312 (2) Å

  • b = 11.243 (2) Å

  • c = 21.283 (4) Å

  • α = 79.565 (3)°

  • β = 88.961 (3)°

  • γ = 85.125 (3)°

  • V = 2418.0 (9) Å3

  • Z = 10

  • Mo Kα radiation

  • μ = 0.20 mm−1

  • T = 100 K

  • 0.14 × 0.11 × 0.11 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2010[Bruker (2010). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.973, Tmax = 0.980

  • 16341 measured reflections

  • 8352 independent reflections

  • 5092 reflections with I > 2σ(I)

  • Rint = 0.046

Refinement
  • R[F2 > 2σ(F2)] = 0.048

  • wR(F2) = 0.151

  • S = 0.85

  • 8352 reflections

  • 771 parameters

  • 6 restraints

  • H-atom parameters constrained

  • Δρmax = 0.28 e Å−3

  • Δρmin = −0.29 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O2—H2⋯O1i 0.84 1.87 2.701 (4) 172
O4—H4A⋯O10ii 0.84 1.82 2.657 (3) 174
O6—H6A⋯O8i 0.84 1.84 2.673 (4) 170
O7—H7⋯O5i 0.84 1.80 2.638 (4) 173
O9—H9⋯O3iii 0.84 1.81 2.644 (3) 174
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x+1, y, z; (iii) x-1, y, z.

Data collection: APEX2 (Bruker, 2010[Bruker (2010). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2010[Bruker (2010). 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: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information


Comment top

Recent studies on benzoic acids have indicated a potential for selective crystal polymorph engineering. It is suggested that catemeric or dimeric structures of benzoic acids can be influenced by concentration and the presence of solvent (Moorthy et al., 2002). Crystallization from solvent free oil led to the formation of the hydrogen bound, dimeric form of the title compound.

The molecular structure of the title compound is presented in Fig. 1. The most significant structural difference between this structure and the literature polymorph (Tobin & Masuda, 2009) is the hydrogen bound, dimeric orientation of the carboxylic acid functionalities. The five molecules in the asymmetric unit are defined by O—H···O hydrogen bonds ranging from 2.638 (4)–2.701 (4) Å and angles of 170–174° (Tab. 1 & Fig. 2).

Related literature top

For the first polymorph of the title compound, see: Tobin & Masuda (2009). For details of the synthesis, see: Dmowski & Piasecka-Macieiewska (1998). For information on dimeric versus catemeric crystal growth in benzoic acids, see: Moorthy et al. (2002).

Experimental top

The title compound was prepared following the literature methods (Dmowski & Piasecka-Macieiewska, 1998). The compound was crystallized slowly from the resultant oil forming colorless, block-like crystals.

Refinement top

The H atoms were placed in geometrically idealized positions with C—H and O—H distances = 0.95 and 0.98Å, respectively, with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(O).

Several short contact distances are found for F(2) & F(4) to F(17), F(8) to F(23), F(9) to F(20), F(10) to F(25), F(13) to F(21) and F(14) to F(27). The short contacts are believed to arise from disorder present in the crystal. Modeling this disorder yielded low occupancy which was detrimental to the integrity of the data set upon refinement. In order to obtain satisfactory thermal parameters the use of DELU restraints were applied to fluorine atoms F(4)>F(6) relative to the adjacent C(8) atom.

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 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with atom labels and 50% probability displacement ellipsoids for non-H atoms. Aromatic hydrogen atoms are removed for clarity.
[Figure 2] Fig. 2. The hydorgen bonding interactions between molecules of the title compound lying about inversion centers. Trifluoromethyl groups and aromatic H atoms are removed for clarity.
2,6-Bis(trifluoromethyl)benzoic acid top
Crystal data top
C9H4F6O2Z = 10
Mr = 258.12F(000) = 1280
Triclinic, P1Dx = 1.773 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.312 (2) ÅCell parameters from 4371 reflections
b = 11.243 (2) Åθ = 2.2–27.4°
c = 21.283 (4) ŵ = 0.20 mm1
α = 79.565 (3)°T = 100 K
β = 88.961 (3)°Block, colourless
γ = 85.125 (3)°0.14 × 0.11 × 0.11 mm
V = 2418.0 (9) Å3
Data collection top
Bruker APEXII CCD
diffractometer
8352 independent reflections
Radiation source: fine-focus sealed tube5092 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.046
ϕ and ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2010)
h = 1112
Tmin = 0.973, Tmax = 0.980k = 1313
16341 measured reflectionsl = 2525
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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151H-atom parameters constrained
S = 0.85 w = 1/[σ2(Fo2) + (0.0887P)2 + 1.2723P]
where P = (Fo2 + 2Fc2)/3
8352 reflections(Δ/σ)max = 0.001
771 parametersΔρmax = 0.28 e Å3
6 restraintsΔρmin = 0.29 e Å3
Crystal data top
C9H4F6O2γ = 85.125 (3)°
Mr = 258.12V = 2418.0 (9) Å3
Triclinic, P1Z = 10
a = 10.312 (2) ÅMo Kα radiation
b = 11.243 (2) ŵ = 0.20 mm1
c = 21.283 (4) ÅT = 100 K
α = 79.565 (3)°0.14 × 0.11 × 0.11 mm
β = 88.961 (3)°
Data collection top
Bruker APEXII CCD
diffractometer
8352 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2010)
5092 reflections with I > 2σ(I)
Tmin = 0.973, Tmax = 0.980Rint = 0.046
16341 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0486 restraints
wR(F2) = 0.151H-atom parameters constrained
S = 0.85Δρmax = 0.28 e Å3
8352 reflectionsΔρmin = 0.29 e Å3
771 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
xyzUiso*/Ueq
F10.2018 (2)0.7426 (2)0.03174 (10)0.0326 (5)
C10.1804 (4)0.6502 (3)0.08995 (16)0.0210 (8)
O10.5747 (2)0.5485 (2)0.55641 (12)0.0268 (6)
F20.0386 (2)0.7786 (2)0.09609 (10)0.0391 (6)
C20.0469 (3)0.6267 (3)0.06966 (16)0.0184 (8)
O20.6703 (2)0.4971 (2)0.46844 (12)0.0286 (6)
H20.59360.48940.45810.043*
F30.0525 (2)0.88431 (19)0.02227 (11)0.0412 (6)
C30.0026 (3)0.6834 (3)0.00950 (17)0.0207 (8)
O30.8142 (2)0.2255 (2)0.30586 (12)0.0256 (6)
C40.1242 (4)0.6592 (3)0.00972 (17)0.0224 (8)
H40.15580.69560.05100.027*
O40.7566 (2)0.0674 (2)0.26430 (12)0.0263 (6)
H4A0.83590.04410.26950.039*
C50.1996 (4)0.5822 (3)0.03096 (17)0.0227 (8)
H50.28310.56650.01790.027*
O50.5766 (2)0.2035 (2)0.86826 (13)0.0313 (6)
C60.1525 (4)0.5288 (3)0.09046 (17)0.0234 (9)
H60.20490.47700.11850.028*
O60.4856 (2)0.3878 (2)0.87912 (12)0.0264 (6)
H6A0.56030.39660.89170.040*
C70.0301 (3)0.5491 (3)0.11012 (16)0.0186 (8)
F70.3484 (2)0.50617 (18)0.75965 (11)0.0366 (6)
O70.1849 (2)0.7599 (2)0.10138 (12)0.0250 (6)
H70.26240.77210.10800.037*
C80.0199 (4)0.4852 (3)0.17366 (17)0.0231 (6)
F80.4944 (2)0.3692 (2)0.74177 (11)0.0434 (6)
O80.2712 (2)0.5717 (2)0.09473 (11)0.0241 (6)
C90.0723 (4)0.7717 (3)0.03502 (17)0.0269 (9)
F90.3243 (3)0.4099 (2)0.68321 (11)0.0577 (8)
O90.0663 (2)0.1576 (2)0.31237 (12)0.0244 (6)
H90.01320.18030.30760.037*
F100.4166 (2)0.00770 (19)0.94653 (11)0.0433 (7)
C100.4828 (4)0.2792 (3)0.86606 (17)0.0233 (8)
O100.0096 (2)0.0017 (2)0.27140 (12)0.0266 (6)
F110.4018 (2)0.17788 (18)0.98037 (10)0.0309 (5)
C110.3507 (3)0.2508 (3)0.84751 (16)0.0199 (8)
F120.2413 (2)0.0653 (2)0.99315 (10)0.0424 (6)
C120.2800 (4)0.1666 (3)0.88805 (16)0.0218 (8)
C130.1607 (4)0.1366 (3)0.87036 (17)0.0252 (9)
H130.11380.08030.89870.030*
F130.0824 (2)0.0491 (2)0.41419 (10)0.0353 (6)
C140.1091 (4)0.1894 (3)0.81057 (17)0.0224 (8)
H140.02700.16910.79800.027*
F140.2542 (2)0.1135 (2)0.46976 (10)0.0400 (6)
C150.1785 (4)0.2714 (3)0.76988 (17)0.0234 (8)
H150.14410.30640.72900.028*
F150.2106 (2)0.07786 (19)0.43794 (10)0.0370 (6)
C160.2977 (4)0.3034 (3)0.78793 (16)0.0217 (8)
F160.1837 (2)0.03585 (18)0.15962 (9)0.0278 (5)
C170.3656 (4)0.3974 (4)0.74290 (18)0.0299 (9)
F170.1763 (2)0.14663 (17)0.17769 (9)0.0273 (5)
C180.3351 (4)0.1034 (3)0.95232 (18)0.0278 (9)
F180.3479 (2)0.07010 (19)0.13671 (9)0.0310 (5)
C190.0905 (4)0.0543 (3)0.29297 (16)0.0211 (8)
F190.6650 (2)0.7594 (2)0.45210 (10)0.0356 (6)
C200.2308 (3)0.0048 (3)0.30006 (16)0.0192 (8)
F200.8213 (2)0.6977 (2)0.39510 (9)0.0365 (6)
C210.3090 (3)0.0021 (3)0.24565 (16)0.0195 (8)
F210.8352 (2)0.85782 (18)0.43459 (10)0.0361 (6)
C220.4375 (4)0.0487 (3)0.25249 (18)0.0223 (8)
H220.49030.05110.21560.027*
F220.9052 (2)0.3168 (2)0.66535 (12)0.0454 (7)
C230.4900 (4)0.0917 (3)0.31231 (18)0.0255 (9)
H230.57790.12480.31640.031*
F230.7250 (2)0.4195 (2)0.67639 (11)0.0417 (6)
C240.4143 (4)0.0866 (3)0.36632 (18)0.0261 (9)
H240.45030.11670.40750.031*
F240.7544 (2)0.32825 (19)0.59631 (11)0.0419 (6)
C250.2858 (3)0.0376 (3)0.36039 (16)0.0202 (8)
F250.6092 (2)0.14615 (19)0.14326 (10)0.0337 (5)
C260.2081 (4)0.0306 (3)0.42061 (18)0.0273 (9)
F260.7286 (2)0.28146 (19)0.16435 (10)0.0320 (5)
C270.2537 (4)0.0439 (3)0.18000 (17)0.0228 (8)
F270.6488 (2)0.26378 (18)0.41950 (9)0.0277 (5)
C280.6694 (4)0.5377 (3)0.52244 (17)0.0237 (8)
F280.4893 (2)0.1538 (2)0.44626 (9)0.0325 (5)
C290.8011 (3)0.5702 (3)0.54062 (16)0.0198 (8)
F290.6595 (2)0.07953 (17)0.40289 (9)0.0281 (5)
C300.8664 (4)0.5031 (3)0.59459 (17)0.0226 (8)
F300.5517 (2)0.3352 (2)0.11093 (10)0.0409 (6)
C310.9828 (4)0.5382 (3)0.61349 (17)0.0259 (9)
H311.02540.49300.65050.031*
C321.0379 (4)0.6378 (3)0.57941 (18)0.0255 (9)
H321.11800.66100.59270.031*
C330.9757 (4)0.7032 (3)0.52601 (17)0.0238 (9)
H331.01360.77160.50230.029*
C340.8579 (4)0.6706 (3)0.50624 (16)0.0210 (8)
C350.7957 (4)0.7459 (3)0.44775 (17)0.0245 (9)
C360.8120 (4)0.3929 (3)0.63253 (18)0.0287 (9)
C370.7321 (4)0.1698 (3)0.28488 (16)0.0205 (8)
C380.5913 (3)0.2176 (3)0.28029 (16)0.0189 (8)
C390.5192 (4)0.2240 (3)0.33629 (16)0.0197 (8)
C400.3908 (4)0.2727 (3)0.33246 (17)0.0226 (8)
H400.34210.27630.37050.027*
C410.3330 (4)0.3163 (3)0.27363 (17)0.0238 (8)
H410.24540.35040.27150.029*
C420.4026 (4)0.3101 (3)0.21823 (17)0.0244 (9)
H420.36260.33940.17790.029*
C430.5319 (4)0.2609 (3)0.22122 (16)0.0216 (8)
C440.6044 (4)0.2552 (3)0.16000 (17)0.0254 (9)
C450.5793 (4)0.1803 (3)0.40084 (17)0.0237 (8)
F40.1004 (2)0.38607 (18)0.16895 (10)0.0319 (5)
F50.0752 (2)0.4452 (2)0.21359 (10)0.0356 (5)
F60.0871 (2)0.55444 (18)0.20437 (9)0.0289 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0198 (13)0.0469 (14)0.0305 (12)0.0067 (10)0.0055 (10)0.0040 (10)
C10.020 (2)0.0212 (18)0.0229 (19)0.0016 (16)0.0007 (16)0.0061 (15)
O10.0138 (14)0.0371 (15)0.0322 (14)0.0036 (11)0.0023 (12)0.0127 (12)
F20.0322 (14)0.0588 (15)0.0219 (11)0.0052 (12)0.0015 (10)0.0054 (11)
C20.0151 (19)0.0191 (17)0.0228 (18)0.0004 (14)0.0000 (15)0.0084 (15)
O20.0157 (14)0.0436 (16)0.0324 (15)0.0070 (13)0.0011 (12)0.0205 (13)
F30.0440 (15)0.0242 (11)0.0533 (15)0.0063 (10)0.0131 (12)0.0006 (11)
C30.014 (2)0.0228 (18)0.0271 (19)0.0001 (15)0.0019 (16)0.0098 (16)
O30.0168 (14)0.0280 (13)0.0340 (15)0.0026 (11)0.0016 (12)0.0103 (12)
C40.021 (2)0.0225 (18)0.0248 (19)0.0048 (16)0.0030 (16)0.0092 (16)
O40.0139 (14)0.0247 (13)0.0415 (15)0.0025 (11)0.0002 (13)0.0113 (12)
C50.016 (2)0.0237 (18)0.031 (2)0.0006 (15)0.0031 (17)0.0123 (17)
O50.0164 (14)0.0317 (14)0.0505 (17)0.0031 (12)0.0024 (13)0.0217 (13)
C60.019 (2)0.0204 (18)0.031 (2)0.0014 (15)0.0047 (17)0.0053 (16)
O60.0175 (15)0.0262 (13)0.0395 (15)0.0010 (11)0.0075 (13)0.0158 (12)
C70.014 (2)0.0190 (17)0.0235 (18)0.0012 (15)0.0011 (15)0.0081 (15)
F70.0372 (14)0.0255 (11)0.0470 (14)0.0088 (10)0.0025 (12)0.0033 (11)
O70.0173 (14)0.0251 (13)0.0356 (15)0.0029 (11)0.0036 (12)0.0128 (12)
C80.0206 (19)0.0219 (16)0.0268 (19)0.0002 (10)0.0001 (13)0.0054 (14)
F80.0318 (15)0.0483 (14)0.0512 (15)0.0117 (11)0.0169 (12)0.0099 (12)
O80.0149 (14)0.0250 (13)0.0333 (14)0.0007 (11)0.0050 (11)0.0085 (11)
C90.023 (2)0.031 (2)0.027 (2)0.0001 (17)0.0004 (17)0.0053 (17)
F90.080 (2)0.0733 (18)0.0228 (13)0.0463 (16)0.0016 (13)0.0012 (12)
O90.0163 (14)0.0250 (13)0.0331 (14)0.0021 (11)0.0002 (12)0.0104 (11)
F100.0571 (17)0.0273 (12)0.0453 (14)0.0187 (12)0.0244 (13)0.0143 (11)
C100.018 (2)0.0258 (19)0.030 (2)0.0022 (16)0.0014 (17)0.0157 (17)
O100.0163 (14)0.0281 (13)0.0383 (15)0.0014 (11)0.0046 (12)0.0135 (12)
F110.0327 (14)0.0293 (11)0.0320 (12)0.0006 (10)0.0128 (10)0.0097 (10)
C110.017 (2)0.0196 (17)0.0255 (19)0.0017 (15)0.0004 (16)0.0102 (15)
F120.0482 (16)0.0463 (14)0.0290 (12)0.0138 (12)0.0048 (12)0.0080 (11)
C120.023 (2)0.0177 (17)0.0257 (19)0.0045 (15)0.0020 (17)0.0081 (15)
C130.025 (2)0.0226 (19)0.029 (2)0.0043 (16)0.0023 (18)0.0062 (16)
F130.0236 (13)0.0486 (14)0.0326 (12)0.0120 (11)0.0047 (10)0.0004 (11)
C140.017 (2)0.0238 (18)0.029 (2)0.0055 (15)0.0042 (16)0.0088 (16)
F140.0439 (15)0.0475 (14)0.0246 (12)0.0004 (12)0.0034 (11)0.0023 (11)
C150.025 (2)0.0231 (18)0.0233 (19)0.0012 (16)0.0055 (17)0.0084 (16)
F150.0412 (15)0.0362 (13)0.0377 (13)0.0073 (11)0.0100 (11)0.0167 (11)
C160.019 (2)0.0232 (18)0.0255 (19)0.0037 (15)0.0017 (16)0.0099 (16)
F160.0269 (13)0.0299 (11)0.0304 (11)0.0039 (10)0.0054 (10)0.0142 (10)
C170.029 (2)0.033 (2)0.030 (2)0.0056 (18)0.0006 (18)0.0095 (18)
F170.0308 (13)0.0216 (11)0.0284 (11)0.0073 (9)0.0059 (10)0.0055 (9)
C180.028 (2)0.0235 (19)0.033 (2)0.0009 (17)0.0071 (19)0.0080 (17)
F180.0270 (13)0.0392 (12)0.0258 (11)0.0035 (10)0.0032 (10)0.0035 (10)
C190.019 (2)0.0226 (18)0.0232 (19)0.0017 (16)0.0003 (16)0.0074 (16)
F190.0186 (12)0.0465 (14)0.0371 (13)0.0052 (10)0.0028 (10)0.0008 (11)
C200.019 (2)0.0149 (16)0.0247 (19)0.0022 (14)0.0017 (16)0.0056 (15)
F200.0402 (15)0.0470 (14)0.0243 (12)0.0007 (11)0.0013 (10)0.0129 (11)
C210.018 (2)0.0140 (16)0.0257 (19)0.0011 (15)0.0031 (16)0.0038 (15)
F210.0414 (15)0.0264 (11)0.0381 (13)0.0028 (10)0.0032 (11)0.0008 (10)
C220.019 (2)0.0167 (17)0.034 (2)0.0030 (15)0.0003 (17)0.0099 (16)
F220.0348 (15)0.0353 (13)0.0569 (16)0.0032 (11)0.0033 (13)0.0139 (12)
C230.016 (2)0.0206 (18)0.039 (2)0.0039 (15)0.0028 (18)0.0049 (17)
F230.0372 (15)0.0417 (13)0.0444 (14)0.0084 (11)0.0167 (12)0.0025 (11)
C240.028 (2)0.0179 (18)0.032 (2)0.0003 (16)0.0050 (18)0.0028 (16)
F240.0456 (16)0.0279 (12)0.0536 (15)0.0161 (11)0.0043 (13)0.0044 (11)
C250.020 (2)0.0166 (17)0.0254 (19)0.0055 (15)0.0000 (16)0.0054 (15)
F250.0370 (14)0.0351 (12)0.0335 (12)0.0105 (10)0.0078 (11)0.0152 (10)
C260.026 (2)0.029 (2)0.027 (2)0.0062 (17)0.0065 (18)0.0004 (17)
F260.0302 (14)0.0381 (12)0.0314 (12)0.0174 (10)0.0097 (10)0.0101 (10)
C270.021 (2)0.0201 (18)0.029 (2)0.0013 (16)0.0031 (17)0.0084 (16)
F270.0247 (12)0.0306 (11)0.0311 (11)0.0046 (10)0.0071 (10)0.0123 (10)
C280.019 (2)0.0261 (19)0.027 (2)0.0002 (16)0.0002 (17)0.0076 (17)
F280.0272 (13)0.0429 (13)0.0253 (11)0.0023 (10)0.0032 (10)0.0008 (10)
C290.0131 (19)0.0220 (18)0.0270 (19)0.0010 (15)0.0011 (16)0.0126 (16)
F290.0290 (13)0.0250 (11)0.0289 (11)0.0071 (10)0.0052 (10)0.0048 (9)
C300.019 (2)0.0233 (18)0.027 (2)0.0003 (16)0.0009 (17)0.0093 (16)
F300.0473 (16)0.0472 (14)0.0243 (12)0.0005 (12)0.0010 (11)0.0015 (11)
C310.023 (2)0.0263 (19)0.029 (2)0.0050 (17)0.0053 (17)0.0077 (17)
C320.018 (2)0.0262 (19)0.035 (2)0.0029 (16)0.0033 (17)0.0102 (17)
C330.019 (2)0.0214 (18)0.033 (2)0.0039 (16)0.0060 (17)0.0087 (17)
C340.021 (2)0.0201 (18)0.0233 (19)0.0019 (15)0.0034 (16)0.0076 (15)
C350.021 (2)0.029 (2)0.025 (2)0.0047 (16)0.0023 (17)0.0075 (17)
C360.023 (2)0.028 (2)0.033 (2)0.0025 (18)0.0043 (19)0.0012 (18)
C370.019 (2)0.0220 (18)0.0214 (18)0.0027 (16)0.0034 (16)0.0051 (16)
C380.0130 (19)0.0169 (17)0.0275 (19)0.0016 (14)0.0010 (16)0.0059 (15)
C390.022 (2)0.0152 (17)0.0226 (18)0.0023 (15)0.0023 (16)0.0045 (15)
C400.019 (2)0.0215 (18)0.029 (2)0.0015 (15)0.0029 (17)0.0084 (16)
C410.017 (2)0.0233 (19)0.031 (2)0.0004 (16)0.0049 (17)0.0068 (16)
C420.026 (2)0.0194 (18)0.027 (2)0.0025 (16)0.0070 (17)0.0023 (16)
C430.022 (2)0.0209 (18)0.0232 (19)0.0049 (16)0.0019 (16)0.0050 (15)
C440.026 (2)0.025 (2)0.026 (2)0.0067 (17)0.0010 (17)0.0023 (17)
C450.018 (2)0.0278 (19)0.027 (2)0.0003 (16)0.0031 (17)0.0093 (17)
F40.0323 (13)0.0240 (10)0.0372 (12)0.0096 (9)0.0095 (10)0.0040 (9)
F50.0306 (12)0.0427 (13)0.0286 (12)0.0050 (9)0.0018 (9)0.0067 (10)
F60.0317 (13)0.0310 (11)0.0250 (11)0.0016 (9)0.0067 (9)0.0076 (9)
Geometric parameters (Å, º) top
F1—C91.347 (4)C16—C171.503 (5)
C1—O81.223 (4)F16—C271.332 (4)
C1—O71.305 (4)F17—C271.340 (4)
C1—C21.509 (5)F18—C271.341 (4)
O1—C281.215 (4)C19—C201.505 (5)
F2—C91.339 (4)F19—C351.347 (4)
C2—C71.398 (5)C20—C251.399 (5)
C2—C31.407 (5)C20—C211.409 (5)
O2—C281.310 (4)F20—C351.343 (4)
O2—H20.8400C21—C221.384 (5)
F3—C91.341 (4)C21—C271.504 (5)
C3—C41.389 (5)F21—C351.336 (4)
C3—C91.498 (5)C22—C231.380 (5)
O3—C371.231 (4)C22—H220.9500
C4—C51.386 (5)F22—C361.346 (4)
C4—H40.9500C23—C241.384 (5)
O4—C371.308 (4)C23—H230.9500
O4—H4A0.8400F23—C361.338 (4)
C5—C61.377 (5)C24—C251.390 (5)
C5—H50.9500C24—H240.9500
O5—C101.229 (4)F24—C361.330 (5)
C6—C71.387 (5)C25—C261.510 (5)
C6—H60.9500F25—C441.335 (4)
O6—C101.303 (4)F26—C441.347 (4)
O6—H6A0.8400F27—C451.345 (4)
C7—C81.490 (5)C28—C291.511 (5)
F7—C171.332 (4)F28—C451.340 (4)
O7—H70.8400C29—C341.396 (5)
C8—F51.338 (4)C29—C301.404 (5)
C8—F61.345 (4)F29—C451.340 (4)
C8—F41.350 (4)C30—C311.383 (5)
F8—C171.340 (5)C30—C361.497 (5)
F9—C171.327 (4)F30—C441.339 (4)
O9—C191.305 (4)C31—C321.379 (5)
O9—H90.8400C31—H310.9500
F10—C181.330 (4)C32—C331.373 (5)
C10—C111.500 (5)C32—H320.9500
O10—C191.229 (4)C33—C341.392 (5)
F11—C181.351 (4)C33—H330.9500
C11—C161.398 (5)C34—C351.494 (5)
C11—C121.404 (5)C37—C381.503 (5)
F12—C181.334 (4)C38—C431.396 (5)
C12—C131.379 (5)C38—C391.403 (5)
C12—C181.519 (5)C39—C401.387 (5)
C13—C141.397 (5)C39—C451.499 (5)
C13—H130.9500C40—C411.385 (5)
F13—C261.344 (4)C40—H400.9500
C14—C151.383 (5)C41—C421.379 (5)
C14—H140.9500C41—H410.9500
F14—C261.334 (4)C42—C431.397 (5)
C15—C161.390 (5)C42—H420.9500
C15—H150.9500C43—C441.499 (5)
F15—C261.338 (4)
O8—C1—O7126.0 (3)C24—C23—H23120.0
O8—C1—C2121.5 (3)C23—C24—C25120.1 (4)
O7—C1—C2112.5 (3)C23—C24—H24120.0
C7—C2—C3118.8 (3)C25—C24—H24120.0
C7—C2—C1120.9 (3)C24—C25—C20120.6 (3)
C3—C2—C1120.3 (3)C24—C25—C26118.3 (3)
C28—O2—H2109.5C20—C25—C26121.1 (3)
C4—C3—C2120.2 (3)F14—C26—F15106.9 (3)
C4—C3—C9118.3 (3)F14—C26—F13106.6 (3)
C2—C3—C9121.5 (3)F15—C26—F13107.0 (3)
C5—C4—C3120.4 (3)F14—C26—C25111.8 (3)
C5—C4—H4119.8F15—C26—C25111.8 (3)
C3—C4—H4119.8F13—C26—C25112.4 (3)
C37—O4—H4A109.5F16—C27—F17107.1 (3)
C6—C5—C4119.5 (4)F16—C27—F18107.1 (3)
C6—C5—H5120.2F17—C27—F18106.1 (3)
C4—C5—H5120.2F16—C27—C21112.7 (3)
C5—C6—C7121.2 (3)F17—C27—C21111.9 (3)
C5—C6—H6119.4F18—C27—C21111.5 (3)
C7—C6—H6119.4O1—C28—O2125.4 (4)
C10—O6—H6A109.5O1—C28—C29121.2 (3)
C6—C7—C2119.9 (3)O2—C28—C29113.4 (3)
C6—C7—C8119.6 (3)C34—C29—C30118.4 (3)
C2—C7—C8120.4 (3)C34—C29—C28121.1 (3)
C1—O7—H7109.5C30—C29—C28120.4 (3)
F5—C8—F6106.1 (3)C31—C30—C29120.1 (3)
F5—C8—F4105.6 (3)C31—C30—C36118.9 (3)
F6—C8—F4106.2 (3)C29—C30—C36120.9 (3)
F5—C8—C7112.7 (3)C32—C31—C30121.0 (4)
F6—C8—C7113.6 (3)C32—C31—H31119.5
F4—C8—C7112.0 (3)C30—C31—H31119.5
F2—C9—F3106.6 (3)C33—C32—C31119.3 (4)
F2—C9—F1106.6 (3)C33—C32—H32120.3
F3—C9—F1106.5 (3)C31—C32—H32120.3
F2—C9—C3112.1 (3)C32—C33—C34120.8 (3)
F3—C9—C3111.8 (3)C32—C33—H33119.6
F1—C9—C3112.7 (3)C34—C33—H33119.6
C19—O9—H9109.5C33—C34—C29120.2 (3)
O5—C10—O6125.4 (3)C33—C34—C35118.0 (3)
O5—C10—C11120.7 (3)C29—C34—C35121.8 (3)
O6—C10—C11113.9 (3)F21—C35—F20105.8 (3)
C16—C11—C12118.3 (3)F21—C35—F19106.2 (3)
C16—C11—C10120.6 (3)F20—C35—F19105.7 (3)
C12—C11—C10121.0 (3)F21—C35—C34113.0 (3)
C13—C12—C11121.4 (3)F20—C35—C34112.7 (3)
C13—C12—C18118.1 (3)F19—C35—C34112.9 (3)
C11—C12—C18120.5 (4)F24—C36—F23107.2 (3)
C12—C13—C14119.8 (3)F24—C36—F22106.1 (3)
C12—C13—H13120.1F23—C36—F22105.4 (3)
C14—C13—H13120.1F24—C36—C30112.9 (3)
C15—C14—C13119.4 (4)F23—C36—C30112.9 (3)
C15—C14—H14120.3F22—C36—C30111.8 (3)
C13—C14—H14120.3O3—C37—O4124.8 (3)
C14—C15—C16121.0 (3)O3—C37—C38121.1 (3)
C14—C15—H15119.5O4—C37—C38114.0 (3)
C16—C15—H15119.5C43—C38—C39119.0 (3)
C15—C16—C11120.1 (3)C43—C38—C37121.3 (3)
C15—C16—C17118.6 (3)C39—C38—C37119.7 (3)
C11—C16—C17121.3 (3)C40—C39—C38120.0 (3)
F9—C17—F7107.2 (3)C40—C39—C45119.0 (3)
F9—C17—F8106.7 (3)C38—C39—C45121.0 (3)
F7—C17—F8106.5 (3)C41—C40—C39120.5 (3)
F9—C17—C16112.5 (3)C41—C40—H40119.7
F7—C17—C16111.9 (3)C39—C40—H40119.7
F8—C17—C16111.7 (3)C42—C41—C40120.0 (3)
F10—C18—F12107.9 (3)C42—C41—H41120.0
F10—C18—F11107.1 (3)C40—C41—H41120.0
F12—C18—F11106.6 (3)C41—C42—C43120.2 (3)
F10—C18—C12111.5 (3)C41—C42—H42119.9
F12—C18—C12111.7 (3)C43—C42—H42119.9
F11—C18—C12111.9 (3)C38—C43—C42120.2 (3)
O10—C19—O9125.4 (3)C38—C43—C44121.0 (3)
O10—C19—C20120.9 (3)C42—C43—C44118.7 (3)
O9—C19—C20113.7 (3)F25—C44—F30106.9 (3)
C25—C20—C21118.5 (3)F25—C44—F26106.5 (3)
C25—C20—C19121.1 (3)F30—C44—F26106.4 (3)
C21—C20—C19120.4 (3)F25—C44—C43113.2 (3)
C22—C21—C20120.1 (3)F30—C44—C43112.1 (3)
C22—C21—C27119.8 (3)F26—C44—C43111.2 (3)
C20—C21—C27120.0 (3)F29—C45—F28106.4 (3)
C23—C22—C21120.7 (3)F29—C45—F27106.9 (3)
C23—C22—H22119.6F28—C45—F27106.2 (3)
C21—C22—H22119.6F29—C45—C39112.6 (3)
C22—C23—C24120.0 (3)F28—C45—C39111.9 (3)
C22—C23—H23120.0F27—C45—C39112.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O1i0.841.872.701 (4)172
O4—H4A···O10ii0.841.822.657 (3)174
O6—H6A···O8i0.841.842.673 (4)170
O7—H7···O5i0.841.802.638 (4)173
O9—H9···O3iii0.841.812.644 (3)174
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y, z; (iii) x1, y, z.

Experimental details

Crystal data
Chemical formulaC9H4F6O2
Mr258.12
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)10.312 (2), 11.243 (2), 21.283 (4)
α, β, γ (°)79.565 (3), 88.961 (3), 85.125 (3)
V3)2418.0 (9)
Z10
Radiation typeMo Kα
µ (mm1)0.20
Crystal size (mm)0.14 × 0.11 × 0.11
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2010)
Tmin, Tmax0.973, 0.980
No. of measured, independent and
observed [I > 2σ(I)] reflections
16341, 8352, 5092
Rint0.046
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.151, 0.85
No. of reflections8352
No. of parameters771
No. of restraints6
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.28, 0.29

Computer programs: APEX2 (Bruker, 2010), SAINT (Bruker, 2010), SAINT (Bruker, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O1i0.841.872.701 (4)172
O4—H4A···O10ii0.841.822.657 (3)174
O6—H6A···O8i0.841.842.673 (4)170
O7—H7···O5i0.841.802.638 (4)173
O9—H9···O3iii0.841.812.644 (3)174
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y, z; (iii) x1, y, z.
 

Acknowledgements

The authors would like to thank the Natural Sciences and Engineering Research Council for a Discovery Grant and a Research Tools and Instruments Grant (JDM), the Canadian Foundation for Innovation for a Leaders Opportunity Fund Grant and the Nova Scotia Research and Innovation Trust (JDM).

References

First citationBruker (2010). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationDmowski, W. & Piasecka-Macieiewska, K. (1998). Tetrahedron, 54, 6781–6792.  Web of Science CrossRef CAS
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals
First citationMacrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457.  Web of Science CrossRef CAS IUCr Journals
First citationMoorthy, J. N., Natarajan, R., Mal, P. & Venugopalan, P. (2002). J. Am. Chem. Soc. 124, 6530–6531.  Web of Science CSD CrossRef PubMed CAS
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationTobin, J. M. & Masuda, J. D. (2009). Acta Cryst. E65, o1217.  Web of Science CSD CrossRef IUCr Journals

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Volume 67| Part 5| May 2011| Page o1054
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