3-[2-Chloro-4-(trifluoro­meth­yl)phen­oxy]benzoic acid

Liu, Y.-J.; Liu, J.

doi:10.1107/S1600536811043479

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o3049

doi:10.1107/S1600536811043479

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3-[2-Chloro-4-(trifluoromethyl)phenoxy]benzoic acid

Yan-Ju Liu ^a ^* and Jie Liu ^b

^aPharmacy College, Henan University of Traditional Chinese Medicine, Zhengzhou 450008, People's Republic of China, and ^bDepartment of Urology, Henan Provincial People's Hospital, Zhengzhou 450003, People's Republic of China
^*Correspondence e-mail: liuyanju886@163.com

(Received 14 October 2011; accepted 19 October 2011; online 29 October 2011)

The asymmetric unit of the title compound, C₁₄H₈ClF₃O₃, comprises two independent molecules. The rings in each molecule are connected together via O—H⋯O hydrogen bonds to form classical hydrogen-bonded carboxylic acid dimers. The dihedral angles between the benzene rings are 80.7 (1) and 68.7 (1)°.

Related literature

For background on applications of the title compound, see: Brown et al. (1997 ). For the synthesis of the title compound, see: Johnson (1977 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₄H₈ClF₃O₃
M_r = 316.66
Triclinic, $[P \overline 1]$
a = 7.3390 (15) Å
b = 7.6880 (15) Å
c = 24.113 (5) Å
α = 90.54 (3)°
β = 92.18 (3)°
γ = 94.23 (3)°
V = 1355.7 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 293 K
0.30 × 0.30 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.909, T_max = 0.968
5407 measured reflections
4984 independent reflections
2318 reflections with I > 2σ(I)
R_int = 0.044
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.068
wR(F²) = 0.167
S = 1.00
4984 reflections
379 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2B⋯O6	0.82	1.79	2.599 (4)	168
O5—H5B⋯O3	0.82	1.82	2.629 (4)	170

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); 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/S1600536811043479/vm2129sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811043479/vm2129Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811043479/vm2129Isup3.cml

checkCIF report

Comment top

The title compound, 3-[2-chloro-4-(trifluoromethyl)phenoxy]benzoic acid is an important intermediate, which can be utilized to synthesize acifluorfen (Brown et al., 1997). Here we report the crystal structure of the title compound Fig. 1). The asymmetric unit contains two molecules with a similar conformation (rms deviation fitting 21 non-H atoms: 0.400 Å) .

Intermolecular O—H···O hydrogen bonds (Table 1, Fig. 2) result in the formation of carboxylic acid dimers. The bond lengths and angles are within normal ranges (Allen et al., 1987). The dihedral angles between the rings A(C1—C6), B(C8—C13), C(C15—C20), D(C22—C27) are: A/B = 80.7 (1)°, C/D = 68.7 (1)°. The O atoms O1 and O4 lie in the benzene ring planes A and B, and C and D, respectively.

Related literature top

For background on applications of the title compound, see: Brown et al. (1997). For the synthesis of the title compound, see: Johnson (1977). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound, (I) was prepared by the method of the Ullmann condensation reaction (Johnson, 1977). The crystals were obtained by dissolving (I) (0.2 g, 0.6 mmol) in ethanol (25 ml) and evaporating the solvent slowly at room temperature for about 5 d.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software (Enraf–Nonius, 1985); data reduction: XCAD4 (Harms & Wocadlo, 1995); 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. The molecular structure of (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A packing diagram of (I). Hydrogen bonds are shown as dashed lines.

3-[2-Chloro-4-(trifluoromethyl)phenoxy]benzoic acid top

Crystal data top

C₁₄H₈ClF₃O₃	Z = 4
M_r = 316.66	F(000) = 640
Triclinic, P1	D_x = 1.551 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3390 (15) Å	Cell parameters from 25 reflections
b = 7.6880 (15) Å	θ = 9–12°
c = 24.113 (5) Å	µ = 0.32 mm⁻¹
α = 90.54 (3)°	T = 293 K
β = 92.18 (3)°	Block, colourless
γ = 94.23 (3)°	0.30 × 0.30 × 0.10 mm
V = 1355.7 (5) Å³

Data collection top

Enraf–Nonius CAD-4 diffractometer	2318 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.044
Graphite monochromator	θ_max = 25.4°, θ_min = 1.7°
ω/2θ scans	h = 0→8
Absorption correction: ψ scan (North et al., 1968)	k = −9→9
T_min = 0.909, T_max = 0.968	l = −29→29
5407 measured reflections	3 standard reflections every 200 reflections
4984 independent reflections	intensity decay: 1%

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.167	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.040P)² + 1.5P] where P = (F_o² + 2F_c²)/3
4984 reflections	(Δ/σ)_max < 0.001
379 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₄H₈ClF₃O₃	γ = 94.23 (3)°
M_r = 316.66	V = 1355.7 (5) Å³
Triclinic, P1	Z = 4
a = 7.3390 (15) Å	Mo Kα radiation
b = 7.6880 (15) Å	µ = 0.32 mm⁻¹
c = 24.113 (5) Å	T = 293 K
α = 90.54 (3)°	0.30 × 0.30 × 0.10 mm
β = 92.18 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2318 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.044
T_min = 0.909, T_max = 0.968	3 standard reflections every 200 reflections
5407 measured reflections	intensity decay: 1%
4984 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.068	0 restraints
wR(F²) = 0.167	H-atom parameters constrained
S = 1.00	Δρ_max = 0.30 e Å⁻³
4984 reflections	Δρ_min = −0.23 e Å⁻³
379 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
Cl1	0.9919 (2)	0.7043 (2)	0.23190 (8)	0.0893 (6)
F1	0.5275 (7)	0.6798 (7)	0.0264 (2)	0.1418 (17)
F2	0.7104 (7)	0.8940 (6)	0.0453 (2)	0.1387 (17)
F3	0.3837 (7)	0.8748 (6)	0.05963 (17)	0.1223 (15)
O1	0.6596 (5)	0.5437 (5)	0.27733 (15)	0.0721 (12)
C1	0.4377 (10)	0.6640 (9)	0.1489 (3)	0.089 (2)
H1A	0.3208	0.6606	0.1325	0.107*
O2	0.3868 (4)	0.2435 (4)	0.43749 (13)	0.0508 (9)
H2B	0.3410	0.1827	0.4618	0.076*
C2	0.4616 (8)	0.5938 (8)	0.1999 (3)	0.0747 (18)
H2A	0.3642	0.5362	0.2174	0.090*
O3	0.2751 (4)	0.4507 (4)	0.48761 (13)	0.0530 (9)
C3	0.6323 (7)	0.6100 (6)	0.2247 (2)	0.0524 (14)
C4	0.7807 (8)	0.6875 (7)	0.1984 (2)	0.0606 (15)
C5	0.7505 (11)	0.7526 (8)	0.1467 (3)	0.082 (2)
H5A	0.8485	0.8071	0.1287	0.098*
C6	0.5840 (12)	0.7410 (9)	0.1208 (3)	0.081 (2)
C7	0.5508 (15)	0.8149 (13)	0.0650 (3)	0.104 (3)
C8	0.5568 (6)	0.5995 (6)	0.3193 (2)	0.0487 (13)
C9	0.5181 (6)	0.7782 (6)	0.3263 (2)	0.0515 (14)
H9A	0.5595	0.8621	0.3013	0.062*
C10	0.4214 (7)	0.8220 (7)	0.3695 (2)	0.0602 (15)
H10A	0.3868	0.9357	0.3719	0.072*
C11	0.3704 (6)	0.7070 (6)	0.4106 (2)	0.0474 (13)
H11A	0.3118	0.7434	0.4417	0.057*
C12	0.4109 (5)	0.5314 (6)	0.40349 (19)	0.0375 (11)
C13	0.5042 (6)	0.4793 (6)	0.35821 (19)	0.0441 (12)
H13A	0.5311	0.3636	0.3542	0.053*
C14	0.3558 (6)	0.4010 (6)	0.4459 (2)	0.0391 (11)
Cl2	−0.43627 (19)	−0.1013 (2)	0.78752 (7)	0.0802 (5)
F4	−0.0534 (7)	−0.4636 (7)	0.94183 (19)	0.1401 (17)
F5	0.1853 (7)	−0.3609 (6)	0.93988 (17)	0.1149 (14)
F6	0.0134 (6)	−0.2118 (6)	0.9690 (2)	0.1243 (16)
O4	−0.1400 (4)	−0.1045 (4)	0.71473 (13)	0.0473 (9)
O5	0.1479 (4)	0.2192 (4)	0.55868 (13)	0.0543 (9)
H5B	0.1906	0.2815	0.5342	0.082*
O6	0.2627 (4)	0.0143 (4)	0.50788 (13)	0.0556 (10)
C15	0.1275 (7)	−0.2544 (7)	0.8357 (2)	0.0587 (15)
H15A	0.2448	−0.2851	0.8452	0.070*
C16	0.0786 (6)	−0.2065 (7)	0.7814 (2)	0.0543 (14)
H16A	0.1662	−0.2086	0.7546	0.065*
C17	−0.0920 (6)	−0.1566 (6)	0.76583 (19)	0.0384 (11)
C18	−0.2194 (6)	−0.1585 (6)	0.8058 (2)	0.0493 (13)
C19	−0.1786 (8)	−0.2077 (7)	0.8604 (2)	0.0623 (15)
H19A	−0.2678	−0.2089	0.8868	0.075*
C20	−0.0074 (8)	−0.2536 (7)	0.8745 (2)	0.0587 (15)
C21	0.0403 (11)	−0.3023 (13)	0.9317 (3)	0.084 (2)
C22	−0.0435 (5)	−0.1560 (6)	0.66983 (17)	0.0336 (11)
C23	−0.0255 (6)	−0.3304 (6)	0.66038 (19)	0.0444 (12)
H23A	−0.0697	−0.4140	0.6851	0.053*
C24	0.0622 (6)	−0.3792 (6)	0.61181 (19)	0.0458 (13)
H24A	0.0742	−0.4963	0.6039	0.055*
C25	0.1299 (6)	−0.2522 (6)	0.57632 (18)	0.0362 (11)
H25A	0.1911	−0.2844	0.5452	0.043*
C26	0.1077 (5)	−0.0778 (6)	0.58650 (18)	0.0339 (10)
C27	0.0201 (6)	−0.0255 (6)	0.63470 (18)	0.0403 (11)
H27A	0.0059	0.0914	0.6424	0.048*
C28	0.1791 (6)	0.0550 (6)	0.54833 (18)	0.0380 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0652 (11)	0.0732 (11)	0.1288 (16)	−0.0061 (8)	0.0134 (10)	0.0146 (10)
F1	0.153 (4)	0.148 (4)	0.124 (4)	0.007 (4)	−0.001 (3)	−0.003 (3)
F2	0.140 (4)	0.145 (4)	0.131 (4)	0.005 (3)	0.012 (3)	0.011 (3)
F3	0.128 (4)	0.129 (4)	0.111 (4)	0.019 (3)	0.001 (3)	0.006 (3)
O1	0.077 (3)	0.080 (3)	0.068 (3)	0.039 (2)	0.045 (2)	0.029 (2)
C1	0.094 (6)	0.097 (5)	0.075 (5)	0.016 (4)	−0.017 (4)	−0.014 (4)
O2	0.058 (2)	0.043 (2)	0.053 (2)	0.0089 (17)	0.0285 (17)	0.0066 (16)
C2	0.071 (5)	0.087 (5)	0.067 (4)	0.011 (4)	0.004 (4)	0.010 (4)
O3	0.058 (2)	0.047 (2)	0.055 (2)	−0.0042 (17)	0.0294 (18)	−0.0059 (17)
C3	0.052 (3)	0.050 (3)	0.057 (4)	0.011 (3)	0.014 (3)	0.009 (3)
C4	0.078 (4)	0.052 (3)	0.053 (4)	−0.001 (3)	0.031 (3)	0.010 (3)
C5	0.112 (6)	0.072 (4)	0.066 (5)	0.009 (4)	0.042 (4)	0.000 (4)
C6	0.115 (6)	0.082 (5)	0.050 (4)	0.031 (5)	0.022 (4)	−0.012 (4)
C7	0.128 (8)	0.112 (7)	0.074 (6)	0.012 (6)	0.006 (6)	0.005 (5)
C8	0.043 (3)	0.054 (3)	0.054 (3)	0.021 (3)	0.018 (3)	0.017 (3)
C9	0.052 (3)	0.047 (3)	0.056 (4)	−0.002 (3)	0.021 (3)	0.013 (3)
C10	0.054 (3)	0.053 (3)	0.077 (4)	0.022 (3)	0.013 (3)	0.024 (3)
C11	0.046 (3)	0.044 (3)	0.054 (3)	0.012 (2)	0.012 (2)	0.003 (2)
C12	0.022 (2)	0.043 (3)	0.047 (3)	−0.001 (2)	0.011 (2)	0.010 (2)
C13	0.034 (3)	0.055 (3)	0.045 (3)	0.004 (2)	0.012 (2)	0.009 (2)
C14	0.037 (3)	0.030 (3)	0.050 (3)	0.000 (2)	0.010 (2)	0.008 (2)
Cl2	0.0459 (9)	0.1133 (13)	0.0872 (12)	0.0282 (8)	0.0288 (8)	0.0293 (10)
F4	0.145 (4)	0.150 (5)	0.123 (4)	0.000 (4)	−0.007 (3)	0.013 (3)
F5	0.120 (4)	0.130 (4)	0.095 (3)	0.011 (3)	0.001 (3)	0.009 (3)
F6	0.140 (4)	0.129 (4)	0.104 (4)	0.010 (3)	0.004 (3)	0.004 (3)
O4	0.0397 (19)	0.056 (2)	0.049 (2)	0.0124 (16)	0.0194 (16)	0.0079 (17)
O5	0.073 (2)	0.042 (2)	0.050 (2)	0.0014 (18)	0.0302 (18)	−0.0007 (16)
O6	0.068 (2)	0.049 (2)	0.051 (2)	−0.0010 (18)	0.0369 (19)	0.0058 (17)
C15	0.050 (3)	0.066 (4)	0.058 (4)	−0.006 (3)	0.007 (3)	−0.002 (3)
C16	0.033 (3)	0.072 (4)	0.057 (4)	−0.006 (3)	0.005 (3)	−0.001 (3)
C17	0.027 (3)	0.050 (3)	0.039 (3)	0.005 (2)	0.009 (2)	0.010 (2)
C18	0.039 (3)	0.067 (4)	0.044 (3)	0.014 (3)	0.020 (2)	0.004 (3)
C19	0.069 (4)	0.077 (4)	0.042 (3)	0.005 (3)	0.016 (3)	0.008 (3)
C20	0.069 (4)	0.047 (3)	0.059 (4)	−0.001 (3)	−0.002 (3)	0.003 (3)
C21	0.065 (5)	0.139 (8)	0.051 (5)	0.010 (5)	0.012 (4)	−0.004 (5)
C22	0.022 (2)	0.046 (3)	0.034 (3)	0.006 (2)	0.012 (2)	0.012 (2)
C23	0.047 (3)	0.040 (3)	0.046 (3)	0.000 (2)	0.008 (2)	0.009 (2)
C24	0.045 (3)	0.040 (3)	0.055 (3)	0.013 (2)	0.017 (3)	0.006 (2)
C25	0.035 (3)	0.039 (3)	0.035 (3)	0.006 (2)	0.011 (2)	−0.006 (2)
C26	0.027 (2)	0.036 (3)	0.041 (3)	0.008 (2)	0.009 (2)	0.006 (2)
C27	0.040 (3)	0.043 (3)	0.039 (3)	0.009 (2)	0.005 (2)	0.009 (2)
C28	0.039 (3)	0.042 (3)	0.034 (3)	0.002 (2)	0.015 (2)	0.007 (2)

Geometric parameters (Å, º) top

Cl1—C4	1.717 (6)	Cl2—C18	1.724 (5)
F1—C7	1.385 (9)	F4—C21	1.401 (9)
F2—C7	1.382 (9)	F5—C21	1.196 (7)
F3—C7	1.344 (9)	F6—C21	1.163 (7)
O1—C8	1.369 (5)	O4—C17	1.342 (5)
O1—C3	1.385 (6)	O4—C22	1.387 (5)
C1—C2	1.356 (8)	O5—C28	1.323 (5)
C1—C6	1.390 (9)	O5—H5B	0.8200
C1—H1A	0.9300	O6—C28	1.222 (5)
O2—C14	1.264 (5)	C15—C20	1.389 (7)
O2—H2B	0.8200	C15—C16	1.403 (7)
C2—C3	1.365 (7)	C15—H15A	0.9300
C2—H2A	0.9300	C16—C17	1.376 (6)
O3—C14	1.257 (5)	C16—H16A	0.9300
C3—C4	1.381 (6)	C17—C18	1.368 (6)
C4—C5	1.362 (8)	C18—C19	1.400 (7)
C5—C6	1.349 (8)	C19—C20	1.362 (7)
C5—H5A	0.9300	C19—H19A	0.9300
C6—C7	1.483 (9)	C20—C21	1.468 (9)
C8—C13	1.370 (6)	C22—C23	1.375 (6)
C8—C9	1.433 (6)	C22—C27	1.385 (5)
C9—C10	1.337 (6)	C23—C24	1.418 (6)
C9—H9A	0.9300	C23—H23A	0.9300
C10—C11	1.378 (6)	C24—C25	1.381 (6)
C10—H10A	0.9300	C24—H24A	0.9300
C11—C12	1.413 (6)	C25—C26	1.384 (5)
C11—H11A	0.9300	C25—H25A	0.9300
C12—C13	1.383 (6)	C26—C27	1.418 (6)
C12—C14	1.485 (6)	C26—C28	1.462 (6)
C13—H13A	0.9300	C27—H27A	0.9300

C8—O1—C3	118.6 (4)	C17—O4—C22	119.4 (3)
C2—C1—C6	121.6 (7)	C28—O5—H5B	109.5
C2—C1—H1A	119.2	C20—C15—C16	116.9 (5)
C6—C1—H1A	119.2	C20—C15—H15A	121.6
C14—O2—H2B	109.5	C16—C15—H15A	121.6
C1—C2—C3	118.2 (6)	C17—C16—C15	123.5 (5)
C1—C2—H2A	120.9	C17—C16—H16A	118.3
C3—C2—H2A	120.9	C15—C16—H16A	118.3
C2—C3—C4	121.9 (5)	O4—C17—C18	118.3 (4)
C2—C3—O1	119.4 (5)	O4—C17—C16	124.6 (4)
C4—C3—O1	118.7 (5)	C18—C17—C16	117.1 (4)
C5—C4—C3	117.7 (6)	C17—C18—C19	121.7 (5)
C5—C4—Cl1	122.6 (5)	C17—C18—Cl2	118.5 (4)
C3—C4—Cl1	119.7 (4)	C19—C18—Cl2	119.8 (4)
C6—C5—C4	122.5 (6)	C20—C19—C18	119.6 (5)
C6—C5—H5A	118.7	C20—C19—H19A	120.2
C4—C5—H5A	118.7	C18—C19—H19A	120.2
C5—C6—C1	118.0 (7)	C19—C20—C15	121.3 (5)
C5—C6—C7	122.4 (8)	C19—C20—C21	120.7 (6)
C1—C6—C7	119.5 (8)	C15—C20—C21	118.0 (6)
F3—C7—F2	126.1 (8)	F6—C21—F5	108.5 (7)
F3—C7—F1	98.6 (7)	F6—C21—F4	106.3 (7)
F2—C7—F1	97.6 (7)	F5—C21—F4	91.8 (7)
F3—C7—C6	111.7 (7)	F6—C21—C20	121.0 (8)
F2—C7—C6	110.8 (8)	F5—C21—C20	117.1 (6)
F1—C7—C6	108.9 (7)	F4—C21—C20	107.6 (6)
O1—C8—C13	117.0 (4)	C23—C22—C27	123.6 (4)
O1—C8—C9	122.8 (4)	C23—C22—O4	119.6 (4)
C13—C8—C9	120.0 (4)	C27—C22—O4	116.6 (4)
C10—C9—C8	118.8 (5)	C22—C23—C24	118.1 (4)
C10—C9—H9A	120.6	C22—C23—H23A	121.0
C8—C9—H9A	120.6	C24—C23—H23A	121.0
C9—C10—C11	123.2 (5)	C25—C24—C23	119.8 (4)
C9—C10—H10A	118.4	C25—C24—H24A	120.1
C11—C10—H10A	118.4	C23—C24—H24A	120.1
C10—C11—C12	117.3 (5)	C24—C25—C26	120.8 (4)
C10—C11—H11A	121.4	C24—C25—H25A	119.6
C12—C11—H11A	121.4	C26—C25—H25A	119.6
C13—C12—C11	121.1 (4)	C25—C26—C27	120.5 (4)
C13—C12—C14	119.2 (4)	C25—C26—C28	120.2 (4)
C11—C12—C14	119.6 (4)	C27—C26—C28	119.4 (4)
C8—C13—C12	119.4 (5)	C22—C27—C26	117.2 (4)
C8—C13—H13A	120.3	C22—C27—H27A	121.4
C12—C13—H13A	120.3	C26—C27—H27A	121.4
O3—C14—O2	122.8 (4)	O6—C28—O5	121.4 (4)
O3—C14—C12	118.7 (4)	O6—C28—C26	120.8 (4)
O2—C14—C12	118.4 (4)	O5—C28—C26	117.8 (4)

C6—C1—C2—C3	4.0 (10)	C20—C15—C16—C17	1.4 (8)
C1—C2—C3—C4	−3.2 (9)	C22—O4—C17—C18	−157.8 (4)
C1—C2—C3—O1	178.3 (5)	C22—O4—C17—C16	23.2 (7)
C8—O1—C3—C2	−56.3 (7)	C15—C16—C17—O4	177.6 (5)
C8—O1—C3—C4	125.2 (5)	C15—C16—C17—C18	−1.5 (8)
C2—C3—C4—C5	1.8 (8)	O4—C17—C18—C19	−178.6 (5)
O1—C3—C4—C5	−179.7 (5)	C16—C17—C18—C19	0.5 (8)
C2—C3—C4—Cl1	179.9 (4)	O4—C17—C18—Cl2	2.3 (6)
O1—C3—C4—Cl1	−1.6 (7)	C16—C17—C18—Cl2	−178.6 (4)
C3—C4—C5—C6	−1.2 (9)	C17—C18—C19—C20	0.6 (8)
Cl1—C4—C5—C6	−179.2 (5)	Cl2—C18—C19—C20	179.6 (4)
C4—C5—C6—C1	2.0 (10)	C18—C19—C20—C15	−0.6 (8)
C4—C5—C6—C7	178.8 (6)	C18—C19—C20—C21	178.7 (6)
C2—C1—C6—C5	−3.5 (10)	C16—C15—C20—C19	−0.3 (8)
C2—C1—C6—C7	179.6 (7)	C16—C15—C20—C21	−179.7 (6)
C5—C6—C7—F3	−146.2 (7)	C19—C20—C21—F6	−52.4 (11)
C1—C6—C7—F3	30.6 (11)	C15—C20—C21—F6	127.0 (8)
C5—C6—C7—F2	−0.2 (11)	C19—C20—C21—F5	171.4 (7)
C1—C6—C7—F2	176.6 (6)	C15—C20—C21—F5	−9.2 (11)
C5—C6—C7—F1	106.0 (9)	C19—C20—C21—F4	69.9 (8)
C1—C6—C7—F1	−77.2 (9)	C15—C20—C21—F4	−110.7 (6)
C3—O1—C8—C13	143.9 (5)	C17—O4—C22—C23	55.1 (6)
C3—O1—C8—C9	−41.9 (7)	C17—O4—C22—C27	−129.0 (4)
O1—C8—C9—C10	−177.9 (5)	C27—C22—C23—C24	−0.3 (7)
C13—C8—C9—C10	−3.9 (8)	O4—C22—C23—C24	175.4 (4)
C8—C9—C10—C11	6.0 (8)	C22—C23—C24—C25	1.3 (7)
C9—C10—C11—C12	−5.3 (8)	C23—C24—C25—C26	−2.2 (7)
C10—C11—C12—C13	2.5 (7)	C24—C25—C26—C27	2.1 (7)
C10—C11—C12—C14	−178.8 (4)	C24—C25—C26—C28	−179.6 (4)
O1—C8—C13—C12	175.6 (4)	C23—C22—C27—C26	0.2 (7)
C9—C8—C13—C12	1.3 (7)	O4—C22—C27—C26	−175.6 (4)
C11—C12—C13—C8	−0.7 (7)	C25—C26—C27—C22	−1.0 (6)
C14—C12—C13—C8	−179.4 (4)	C28—C26—C27—C22	−179.3 (4)
C13—C12—C14—O3	178.2 (4)	C25—C26—C28—O6	−1.7 (7)
C11—C12—C14—O3	−0.5 (7)	C27—C26—C28—O6	176.6 (4)
C13—C12—C14—O2	−4.1 (7)	C25—C26—C28—O5	177.3 (4)
C11—C12—C14—O2	177.1 (4)	C27—C26—C28—O5	−4.4 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2B···O6	0.82	1.79	2.599 (4)	168
O5—H5B···O3	0.82	1.82	2.629 (4)	170

Experimental details

Crystal data
Chemical formula	C₁₄H₈ClF₃O₃
M_r	316.66
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.3390 (15), 7.6880 (15), 24.113 (5)
α, β, γ (°)	90.54 (3), 92.18 (3), 94.23 (3)
V (Å³)	1355.7 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.32
Crystal size (mm)	0.30 × 0.30 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.909, 0.968
No. of measured, independent and observed [I > 2σ(I)] reflections	5407, 4984, 2318
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.603

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.068, 0.167, 1.00
No. of reflections	4984
No. of parameters	379
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.23

Computer programs: CAD-4 Software (Enraf–Nonius, 1985), XCAD4 (Harms & Wocadlo, 1995), 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
O2—H2B···O6	0.8200	1.7900	2.599 (4)	168.00
O5—H5B···O3	0.8200	1.8200	2.629 (4)	170.00

Acknowledgements

This work was supported by the Science and Technology Department, Henan Province (grant No. 102102310321) and the Doctoral Research Fund of Henan Chinese Medicine. The authors thank the Center of Testing and Analysis, Nanjing University for data collection.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Brown, S. A., Muxworthy, J. P. & Lennon, M. (1997). WO Patent No. 9710199. Google Scholar
Enraf–Nonius (1985). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Johnson, W. O. (1977). US Patent No. 4031131. Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar