2-Carb­oxy-5-(trifluoro­meth­yl)phenyl acetate

Zhang, R.; Wang, D.; Ma, C.; Li, Z.

doi:10.1107/S1600536807055171

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2-Carboxy-5-(trifluoromethyl)phenyl acetate

R. Zhang, D. Wang, C. Ma and Z. Li

The asymmetric unit of the title compound, C₁₀H₇F₃O₄, contains two independent molecules. In one of the molecules, the F atoms of the rifluoromethyl group are disordered over two positions with site occupation factors 0.231 (11)/0.769 (11). The intramolecular C—H

O hydrogen bond results in the formation of a planar five-membered ring, which is oriented at a dihedral angle of 4.24 (3)° with respect to the six-membered ring. In the crystal structure, C—H

F and O—H

O hydrogen bonds link the molecules.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807055171/hk2360sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807055171/hk2360Isup2.hkl Contains datablock I

CCDC reference: 672870

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.008 Å
Disorder in main residue
R factor = 0.070
wR factor = 0.206
Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         40 Perc.
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C11
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C18
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C20
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C8
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C10
PLAT301_ALERT_3_C Main Residue  Disorder .........................       8.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          8
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C19
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety         C9
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C10 H7 F3 O4

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  13 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Benzoic acid derivatives represent an interesting class of compounds possessing broad spectrum biological activities (Nakagawa et al., 1996; Wang et al., 1999). These compounds are known to exhibit diverse biological effects, such as insecticidal and fungicidal activities (Wang et al., 1999). We report herein the crystal structure of the title compound, (I).

The asymmetric unit of the title compound, (I), contains two independent molecules, in which the bond lengths and angles are within normal ranges (Allen et al., 1987).

When the crystal structure was solved, the atoms F4, F5 and F6 were found to be disordered.

The intramolecular C—H···O hydrogen bond (Table 1) results in the formation of the planar five-membered ring; A (O1/C1/C2/C7/H7A), which is oriented with respect to ring B (C2—C7) at a dihedral angle of 4.24 (3)°.

In the crystal structure, C—H···F and O—H···O hydrogen bonds (Table 1) link the molecules, in which they may be effective in the stabilization of the structure.

Related literature top

For related literature, see: Nakagawa et al. (1996); Wang et al. (1999). For bond-length data, see: Allen et al. (1987).

Experimental top

For the preparation of the title compound, 2-Hydroxy-4-trifluoromethylbenzoic acid (0.62 g, 2 mmol) and acetyl chloride (0.69 g, 5 mmol) were added in a flask (25 ml) and reacted in an oil bath (363 K) for 6 h. After cooling and filtering, crude compound, (I) was obtained. Crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of an acetone solution (m.p. 480 K).

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top

Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen bond is shown as dashed lines.

2-Carboxy-5-(trifluoromethyl)phenyl acetate top

Crystal data top

C₁₀H₇F₃O₄	F(000) = 1008
M_r = 248.16	D_x = 1.537 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 480 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 14.558 (3) Å	Cell parameters from 25 reflections
b = 5.7520 (12) Å	θ = 9–12°
c = 26.243 (5) Å	µ = 0.15 mm⁻¹
β = 102.56 (3)°	T = 298 K
V = 2144.9 (8) Å³	Block, colorless
Z = 8	0.40 × 0.10 × 0.10 mm

Data collection top

Nonius CAD-4 diffractometer	1674 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.044
Graphite monochromator	θ_max = 26.0°, θ_min = 1.5°
ω/2θ scans	h = −17→17
Absorption correction: ψ scan (North et al., 1968)	k = 0→7
T_min = 0.942, T_max = 0.985	l = 0→32
4356 measured reflections	3 standard reflections every 120 min
4184 independent reflections	intensity decay: none

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.070	H-atom parameters constrained
wR(F²) = 0.206	w = 1/[σ²(F_o²) + (0.060P)² + 1.5P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
4184 reflections	Δρ_max = 0.21 e Å⁻³
335 parameters	Δρ_min = −0.19 e Å⁻³
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₀H₇F₃O₄	V = 2144.9 (8) Å³
M_r = 248.16	Z = 8
Monoclinic, P2₁/n	Mo Kα radiation
a = 14.558 (3) Å	µ = 0.15 mm⁻¹
b = 5.7520 (12) Å	T = 298 K
c = 26.243 (5) Å	0.40 × 0.10 × 0.10 mm
β = 102.56 (3)°

Data collection top

Nonius CAD-4 diffractometer	1674 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.044
T_min = 0.942, T_max = 0.985	3 standard reflections every 120 min
4356 measured reflections	intensity decay: none
4184 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.070	335 parameters
wR(F²) = 0.206	H-atom parameters constrained
S = 1.02	Δρ_max = 0.21 e Å⁻³
4184 reflections	Δρ_min = −0.19 e Å⁻³

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	Occ. (<1)
O1	0.9999 (3)	−0.2926 (8)	0.04713 (16)	0.1174 (15)
H1A	1.0431	−0.3851	0.0565	0.176*
O2	0.9372 (3)	−0.4915 (8)	0.10301 (17)	0.1049 (13)
O3	0.8243 (4)	−0.1993 (9)	0.17950 (19)	0.1314 (18)
O4	0.7574 (2)	−0.3920 (7)	0.10665 (16)	0.0890 (11)
F1	0.5505 (3)	0.1828 (7)	−0.02489 (16)	0.1326 (14)
F2	0.6350 (2)	0.4848 (6)	−0.00741 (15)	0.1153 (12)
F3	0.5733 (2)	0.3315 (6)	0.05013 (14)	0.1173 (12)
C1	0.9332 (4)	−0.3349 (10)	0.0722 (2)	0.0842 (16)
C2	0.8526 (4)	−0.1699 (9)	0.0581 (2)	0.0782 (15)
C3	0.7697 (3)	−0.2003 (9)	0.0766 (2)	0.0748 (14)
C4	0.6952 (4)	−0.0522 (9)	0.0618 (2)	0.0778 (15)
H4A	0.6411	−0.0746	0.0746	0.093*
C5	0.6992 (3)	0.1293 (9)	0.02827 (19)	0.0695 (13)
C6	0.7798 (4)	0.1678 (10)	0.0096 (2)	0.0853 (16)
H6A	0.7840	0.2924	−0.0124	0.102*
C7	0.8543 (4)	0.0139 (10)	0.0247 (2)	0.0841 (16)
H7A	0.9080	0.0361	0.0116	0.101*
C8	0.7885 (4)	−0.3724 (13)	0.1602 (3)	0.0923 (18)
C9	0.7701 (5)	−0.5929 (12)	0.1860 (3)	0.136 (3)
H9A	0.7920	−0.5783	0.2231	0.204*
H9B	0.8028	−0.7182	0.1735	0.204*
H9C	0.7038	−0.6245	0.1780	0.204*
C10	0.6158 (4)	0.2812 (11)	0.0115 (2)	0.0836 (15)
O5	1.0815 (3)	−0.7810 (7)	0.12631 (17)	0.1112 (14)
H5A	1.0396	−0.6846	0.1175	0.167*
O6	1.1450 (3)	−0.5743 (7)	0.07251 (16)	0.1043 (13)
O7	1.2003 (3)	−0.9896 (9)	0.23943 (17)	0.1168 (16)
O8	1.1704 (2)	−1.1778 (6)	0.16344 (13)	0.0803 (10)
F4	1.5198 (4)	−1.2824 (17)	0.2164 (3)	0.135 (3)	0.769 (11)
F5	1.5193 (5)	−1.3647 (14)	0.1369 (3)	0.150 (3)	0.769 (11)
F6	1.5774 (4)	−1.0544 (13)	0.1709 (4)	0.141 (3)	0.769 (11)
F4'	1.4989 (14)	−1.428 (4)	0.1841 (11)	0.126 (7)	0.231 (11)
F5'	1.5587 (15)	−1.187 (5)	0.1397 (8)	0.114 (7)	0.231 (11)
F6'	1.5503 (15)	−1.089 (4)	0.2094 (9)	0.122 (7)	0.231 (11)
C11	1.1474 (4)	−0.7344 (10)	0.1058 (2)	0.0805 (15)
C12	1.2380 (3)	−0.8623 (10)	0.1208 (2)	0.0761 (14)
C13	1.3175 (4)	−0.7777 (10)	0.1073 (2)	0.0881 (16)
H13A	1.3125	−0.6433	0.0871	0.106*
C14	1.4036 (4)	−0.8814 (10)	0.1219 (2)	0.0833 (16)
H14A	1.4560	−0.8176	0.1123	0.100*
C15	1.4113 (4)	−1.0808 (10)	0.1510 (2)	0.0814 (15)
C16	1.3343 (3)	−1.1774 (9)	0.1659 (2)	0.0803 (15)
H16A	1.3406	−1.3119	0.1860	0.096*
C17	1.2476 (4)	−1.0697 (9)	0.15023 (19)	0.0717 (14)
C18	1.1530 (4)	−1.1230 (12)	0.2111 (2)	0.0838 (16)
C19	1.0710 (4)	−1.2563 (13)	0.2207 (2)	0.117 (2)
H19A	1.0596	−1.2147	0.2542	0.175*
H19B	1.0841	−1.4198	0.2201	0.175*
H19C	1.0165	−1.2206	0.1940	0.175*
C20	1.5044 (4)	−1.2004 (14)	0.1687 (3)	0.0947 (18)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.098 (3)	0.131 (4)	0.135 (3)	0.048 (3)	0.049 (2)	0.038 (3)
O2	0.094 (3)	0.093 (3)	0.133 (3)	0.025 (2)	0.037 (2)	0.027 (3)
O3	0.174 (5)	0.102 (4)	0.113 (4)	−0.014 (4)	0.021 (3)	0.001 (3)
O4	0.088 (2)	0.073 (3)	0.107 (3)	0.005 (2)	0.022 (2)	0.018 (2)
F1	0.105 (2)	0.119 (3)	0.155 (3)	0.014 (2)	−0.012 (2)	−0.020 (3)
F2	0.108 (2)	0.093 (2)	0.153 (3)	0.024 (2)	0.045 (2)	0.035 (2)
F3	0.111 (2)	0.127 (3)	0.128 (3)	0.042 (2)	0.057 (2)	0.011 (2)
C1	0.078 (3)	0.081 (4)	0.096 (4)	0.019 (3)	0.024 (3)	0.006 (3)
C2	0.082 (3)	0.054 (3)	0.103 (4)	0.014 (3)	0.029 (3)	0.001 (3)
C3	0.068 (3)	0.066 (4)	0.092 (4)	0.009 (3)	0.019 (3)	0.000 (3)
C4	0.081 (3)	0.072 (4)	0.089 (4)	0.005 (3)	0.037 (3)	0.005 (3)
C5	0.065 (3)	0.067 (3)	0.078 (3)	0.010 (3)	0.020 (3)	0.001 (3)
C6	0.088 (4)	0.078 (4)	0.096 (4)	0.019 (3)	0.034 (3)	0.016 (3)
C7	0.079 (3)	0.083 (4)	0.097 (4)	0.011 (3)	0.033 (3)	0.006 (3)
C8	0.084 (4)	0.094 (4)	0.098 (5)	0.011 (3)	0.016 (3)	0.026 (4)
C9	0.151 (6)	0.120 (5)	0.135 (5)	−0.004 (5)	0.027 (4)	0.047 (4)
C10	0.085 (4)	0.074 (4)	0.095 (4)	0.013 (3)	0.025 (3)	0.011 (3)
O5	0.090 (3)	0.104 (3)	0.152 (3)	0.027 (2)	0.053 (2)	0.039 (3)
O6	0.111 (3)	0.103 (3)	0.112 (3)	0.037 (2)	0.051 (2)	0.030 (3)
O7	0.114 (3)	0.140 (4)	0.111 (3)	−0.026 (3)	0.055 (3)	−0.048 (3)
O8	0.078 (2)	0.084 (3)	0.083 (2)	0.002 (2)	0.0255 (18)	0.002 (2)
F4	0.097 (4)	0.185 (7)	0.125 (4)	0.031 (4)	0.027 (3)	0.059 (4)
F5	0.140 (5)	0.136 (5)	0.166 (5)	0.060 (4)	0.014 (4)	−0.038 (4)
F6	0.087 (3)	0.142 (5)	0.194 (7)	−0.014 (3)	0.034 (4)	0.013 (5)
F4'	0.124 (10)	0.109 (8)	0.146 (12)	0.006 (8)	0.029 (8)	0.009 (8)
F5'	0.100 (9)	0.139 (12)	0.111 (10)	0.027 (8)	0.038 (7)	0.006 (8)
F6'	0.117 (10)	0.129 (10)	0.117 (10)	0.013 (8)	0.016 (7)	−0.017 (8)
C11	0.085 (3)	0.077 (4)	0.086 (4)	0.016 (3)	0.032 (3)	0.009 (3)
C12	0.074 (3)	0.081 (4)	0.080 (3)	0.011 (3)	0.031 (3)	0.004 (3)
C13	0.091 (4)	0.080 (4)	0.100 (4)	0.023 (3)	0.036 (3)	0.021 (3)
C14	0.078 (3)	0.085 (4)	0.095 (4)	0.002 (3)	0.037 (3)	0.011 (3)
C15	0.082 (4)	0.080 (4)	0.089 (4)	0.020 (3)	0.035 (3)	0.010 (3)
C16	0.078 (3)	0.074 (4)	0.094 (4)	0.011 (3)	0.029 (3)	0.007 (3)
C17	0.076 (3)	0.073 (4)	0.070 (3)	0.000 (3)	0.023 (3)	0.001 (3)
C18	0.078 (3)	0.094 (4)	0.084 (4)	0.015 (3)	0.029 (3)	−0.006 (3)
C19	0.106 (4)	0.138 (5)	0.120 (5)	−0.015 (4)	0.053 (4)	0.002 (4)
C20	0.077 (4)	0.113 (5)	0.097 (4)	0.003 (4)	0.023 (3)	0.009 (4)

Geometric parameters (Å, º) top

O1—C1	1.309 (6)	O6—C11	1.264 (6)
O1—H1A	0.8200	O7—C18	1.181 (6)
O2—C1	1.203 (5)	O8—C18	1.364 (6)
O3—C8	1.185 (7)	O8—C17	1.393 (5)
O4—C8	1.385 (7)	F4—C20	1.310 (8)
O4—C3	1.389 (6)	F5—C20	1.310 (9)
F1—C10	1.320 (6)	F6—C20	1.347 (9)
F2—C10	1.326 (6)	F4'—C20	1.38 (2)
F3—C10	1.328 (6)	F5'—C20	1.213 (19)
C1—C2	1.492 (7)	F6'—C20	1.298 (19)
C2—C7	1.377 (7)	C11—C12	1.487 (7)
C2—C3	1.407 (6)	C12—C13	1.371 (7)
C3—C4	1.368 (6)	C12—C17	1.412 (7)
C4—C5	1.376 (6)	C13—C14	1.365 (7)
C4—H4A	0.9300	C13—H13A	0.9300
C5—C6	1.385 (6)	C14—C15	1.369 (7)
C5—C10	1.483 (7)	C14—H14A	0.9300
C6—C7	1.389 (7)	C15—C16	1.381 (6)
C6—H6A	0.9300	C15—C20	1.501 (8)
C7—H7A	0.9300	C16—C17	1.386 (6)
C8—C9	1.489 (8)	C16—H16A	0.9300
C9—H9A	0.9600	C18—C19	1.486 (8)
C9—H9B	0.9600	C19—H19A	0.9600
C9—H9C	0.9600	C19—H19B	0.9600
O5—C11	1.227 (5)	C19—H19C	0.9600
O5—H5A	0.8200

C1—O1—H1A	109.5	C14—C13—C12	123.1 (5)
C8—O4—C3	117.2 (5)	C14—C13—H13A	118.4
O2—C1—O1	123.0 (5)	C12—C13—H13A	118.4
O2—C1—C2	124.3 (5)	C13—C14—C15	118.8 (5)
O1—C1—C2	112.7 (5)	C13—C14—H14A	120.6
C7—C2—C3	116.8 (5)	C15—C14—H14A	120.6
C7—C2—C1	121.7 (5)	C14—C15—C16	121.4 (5)
C3—C2—C1	121.5 (5)	C14—C15—C20	121.1 (5)
C4—C3—O4	117.6 (5)	C16—C15—C20	117.5 (5)
C4—C3—C2	120.8 (5)	C15—C16—C17	118.6 (5)
O4—C3—C2	121.4 (5)	C15—C16—H16A	120.7
C3—C4—C5	120.9 (5)	C17—C16—H16A	120.7
C3—C4—H4A	119.6	C16—C17—O8	117.4 (5)
C5—C4—H4A	119.6	C16—C17—C12	121.0 (5)
C4—C5—C6	120.4 (5)	O8—C17—C12	121.6 (5)
C4—C5—C10	119.4 (5)	O7—C18—O8	121.9 (5)
C6—C5—C10	120.2 (5)	O7—C18—C19	127.4 (6)
C5—C6—C7	117.8 (5)	O8—C18—C19	110.6 (6)
C5—C6—H6A	121.1	C18—C19—H19A	109.5
C7—C6—H6A	121.1	C18—C19—H19B	109.5
C2—C7—C6	123.4 (5)	H19A—C19—H19B	109.5
C2—C7—H7A	118.3	C18—C19—H19C	109.5
C6—C7—H7A	118.3	H19A—C19—H19C	109.5
O3—C8—O4	121.2 (6)	H19B—C19—H19C	109.5
O3—C8—C9	128.9 (7)	F5'—C20—F6'	101.2 (16)
O4—C8—C9	109.9 (6)	F5'—C20—F5	54.9 (13)
C8—C9—H9A	109.5	F6'—C20—F5	138.8 (10)
C8—C9—H9B	109.5	F5'—C20—F4	128.5 (11)
H9A—C9—H9B	109.5	F6'—C20—F4	56.2 (12)
C8—C9—H9C	109.5	F5—C20—F4	109.4 (8)
H9A—C9—H9C	109.5	F5'—C20—F6	51.0 (13)
H9B—C9—H9C	109.5	F6'—C20—F6	52.9 (11)
F1—C10—F2	106.6 (5)	F5—C20—F6	103.7 (7)
F1—C10—F3	105.3 (5)	F4—C20—F6	102.4 (7)
F2—C10—F3	105.3 (5)	F5'—C20—F4'	109.3 (16)
F1—C10—C5	112.1 (5)	F6'—C20—F4'	106.4 (16)
F2—C10—C5	113.9 (5)	F5—C20—F4'	61.9 (11)
F3—C10—C5	112.9 (5)	F4—C20—F4'	52.2 (10)
C11—O5—H5A	109.5	F6—C20—F4'	132.6 (10)
C18—O8—C17	116.4 (4)	F5'—C20—C15	116.4 (11)
O5—C11—O6	123.7 (5)	F6'—C20—C15	107.3 (11)
O5—C11—C12	120.6 (5)	F5—C20—C15	113.4 (6)
O6—C11—C12	115.6 (5)	F4—C20—C15	114.6 (6)
C13—C12—C17	116.9 (5)	F6—C20—C15	112.2 (6)
C13—C12—C11	120.4 (5)	F4'—C20—C15	114.9 (10)
C17—C12—C11	122.6 (5)

O2—C1—C2—C7	176.4 (6)	O6—C11—C12—C17	−168.8 (5)
O1—C1—C2—C7	−4.1 (8)	C17—C12—C13—C14	−1.5 (8)
O2—C1—C2—C3	−6.2 (9)	C11—C12—C13—C14	176.9 (5)
O1—C1—C2—C3	173.3 (5)	C12—C13—C14—C15	0.8 (9)
C8—O4—C3—C4	−96.5 (6)	C13—C14—C15—C16	−0.4 (8)
C8—O4—C3—C2	89.1 (6)	C13—C14—C15—C20	−179.3 (6)
C7—C2—C3—C4	−0.1 (8)	C14—C15—C16—C17	0.8 (8)
C1—C2—C3—C4	−177.7 (5)	C20—C15—C16—C17	179.7 (5)
C7—C2—C3—O4	174.1 (5)	C15—C16—C17—O8	176.7 (5)
C1—C2—C3—O4	−3.4 (8)	C15—C16—C17—C12	−1.6 (8)
O4—C3—C4—C5	−174.1 (4)	C18—O8—C17—C16	87.5 (6)
C2—C3—C4—C5	0.3 (8)	C18—O8—C17—C12	−94.3 (6)
C3—C4—C5—C6	−1.1 (8)	C13—C12—C17—C16	1.9 (7)
C3—C4—C5—C10	177.8 (5)	C11—C12—C17—C16	−176.5 (5)
C4—C5—C6—C7	1.8 (8)	C13—C12—C17—O8	−176.3 (5)
C10—C5—C6—C7	−177.1 (5)	C11—C12—C17—O8	5.4 (8)
C3—C2—C7—C6	0.8 (8)	C17—O8—C18—O7	0.7 (8)
C1—C2—C7—C6	178.3 (5)	C17—O8—C18—C19	−178.1 (5)
C5—C6—C7—C2	−1.6 (8)	C14—C15—C20—F5'	−33 (2)
C3—O4—C8—O3	−0.3 (8)	C16—C15—C20—F5'	148.4 (18)
C3—O4—C8—C9	−179.8 (5)	C14—C15—C20—F6'	79.8 (16)
C4—C5—C10—F1	−77.8 (7)	C16—C15—C20—F6'	−99.1 (16)
C6—C5—C10—F1	101.1 (6)	C14—C15—C20—F5	−93.6 (9)
C4—C5—C10—F2	161.1 (5)	C16—C15—C20—F5	87.5 (9)
C6—C5—C10—F2	−20.0 (8)	C14—C15—C20—F4	139.9 (8)
C4—C5—C10—F3	41.0 (7)	C16—C15—C20—F4	−39.1 (10)
C6—C5—C10—F3	−140.1 (5)	C14—C15—C20—F6	23.6 (10)
O5—C11—C12—C13	−165.1 (5)	C16—C15—C20—F6	−155.4 (7)
O6—C11—C12—C13	12.9 (8)	C14—C15—C20—F4'	−162.2 (14)
O5—C11—C12—C17	13.2 (9)	C16—C15—C20—F4'	18.9 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O6	0.82	1.81	2.631 (7)	174
O5—H5A···O2	0.82	1.83	2.646 (7)	172
C7—H7A···O1	0.93	2.39	2.721 (7)	101
C13—H13A···F2ⁱ	0.93	2.55	3.313 (7)	140

Symmetry code: (i) −x+2, −y, −z.

Experimental details

Crystal data
Chemical formula	C₁₀H₇F₃O₄
M_r	248.16
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	14.558 (3), 5.7520 (12), 26.243 (5)
β (°)	102.56 (3)
V (Å³)	2144.9 (8)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.15
Crystal size (mm)	0.40 × 0.10 × 0.10

Data collection
Diffractometer	Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.942, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	4356, 4184, 1674
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.616

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.070, 0.206, 1.02
No. of reflections	4184
No. of parameters	335
No. of restraints	?
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.19

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Siemens, 1996).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O6	0.82	1.81	2.631 (7)	174
O5—H5A···O2	0.82	1.83	2.646 (7)	172
C7—H7A···O1	0.93	2.39	2.721 (7)	101
C13—H13A···F2ⁱ	0.93	2.55	3.313 (7)	140

Symmetry code: (i) −x+2, −y, −z.

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