1-[4-(3,5-Difluoro­benz­yloxy)-2-hy­droxy­phen­yl]ethanone

Ma, Y.-T.; Zhang, A.-L.; Yuan, M.-S.; Gao, J.-M.

doi:10.1107/S1600536810033787

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 9| September 2010| Page o2468

https://doi.org/10.1107/S1600536810033787

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1-[4-(3,5-Difluorobenzyloxy)-2-hydroxyphenyl]ethanone

Ya-Tuan Ma,^a An-Ling Zhang,^a Mao-Sen Yuan ^a and Jin-Ming Gao ^a ^*

^aCollege of Science, Northwest A&F University, Yangling 712100, People's Republic of China
^*Correspondence e-mail: jinminggaocn@yahoo.com.cn

(Received 22 July 2010; accepted 21 August 2010; online 28 August 2010)

The title compound, C₁₅H₁₂F₂O₃, has been obtained by the reaction of 2,4-dihydroxylacetonephenone, potassium carbonate and 3,5-difluorobenzyl bromide. The hydroxy group is involved in an intramolecular O—H⋯O hydrogen bond in each of the two independent molecules in the asymmetric unit. The dihedral angle between the aromatic rings is 0.5 (2)° in one molecule and 1.9 (2)° in the other. In the crystal, weak C—H⋯O interactions link the molecules into tetrameric units aligned perpendicular to b.

Related literature

For background to the Williamson reaction in organic synthesis, see: Dermer (1934 ). For a related structure, see: Ma et al. (2010 ).

Experimental

Crystal data

C₁₅H₁₂F₂O₃
M_r = 278.25
Triclinic, $[P \overline 1]$
a = 7.4220 (8) Å
b = 13.0329 (14) Å
c = 14.1171 (16) Å
α = 83.921 (2)°
β = 77.913 (1)°
γ = 76.501 (1)°
V = 1296.1 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 298 K
0.40 × 0.32 × 0.28 mm

Data collection

Siemens SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.955, T_max = 0.968
6817 measured reflections
4491 independent reflections
2244 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.072
wR(F²) = 0.231
S = 0.96
4491 reflections
363 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1	0.82	1.81	2.533 (4)	147
O5—H5⋯O4	0.82	1.80	2.525 (4)	147
C8—H8⋯O5	0.93	2.49	3.382 (5)	161
C13—H13⋯O1ⁱ	0.93	2.44	3.342 (5)	165
C28—H28⋯O4ⁱⁱ	0.93	2.40	3.315 (5)	168
Symmetry codes: (i) x+1, y, z-1; (ii) x-1, y, z+1.

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810033787/bv2156sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810033787/bv2156Isup2.hkl

checkCIF report

Comment top

The Williamson reaction is a very useful transformation in organic synthesis since the products are of value in both industrial and academic applications. It usually involves the employment of an alkali-metal salt of the hydroxy compound and an alkylhalide (Dermer, 1934).

In this paper, we present the title compound, (I), which was synthesized by the reaction of 2,4-dihydroxylacetonephenone, potassium carbonate and 3,5-difluorobenzyl bromide. In (I) (Fig. 1), the bond lengths and angles are normal and the dihedral angle between the aromatic rings is 0.51 (4)°. In addition to the intramolecular O—H···O hydrogen bonds, there are weak C—H···O interactions which link the molecules into tetrameric units aligned perpendicular to b (see Fig. 2).

Related literature top

For background to the Williamson reaction in organic synthesis, see: Dermer (1934). For a related structure, see: Ma et al. (2010).

Experimental top

2,4-Dihydroxylacetonephenone (4 mmol), potassium carbonate (8 mmol), 3,5-difluorobenzyl bromide (4 mmol), and 40 ml acetone were mixed in 100 ml flask. After 3 h stirring at 331 K, the crude product was obtained. The crystals were obtained by recrystallization from n-hexane/ethyl acetate.

Structure description top

For background to the Williamson reaction in organic synthesis, see: Dermer (1934). For a related structure, see: Ma et al. (2010).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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). Displacement ellipsoids are drawn at the 30% probability level. Both the C—H···O interaction and the intramolecular hydrogen bonds are shown by dashed lines.
	Fig. 2. The packing viewed down the b axis showing the tetrameric units linked by C—H···O interactions. Both these interactions and the intramolecular hydrogen bonds are shown by dashed lines.

(I) top

Crystal data top

C₁₅H₁₂F₂O₃	Z = 4
M_r = 278.25	F(000) = 576
Triclinic, P1	D_x = 1.426 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4220 (8) Å	Cell parameters from 1571 reflections
b = 13.0329 (14) Å	θ = 2.4–23.0°
c = 14.1171 (16) Å	µ = 0.12 mm⁻¹
α = 83.921 (2)°	T = 298 K
β = 77.913 (1)°	Triclinic, colorless
γ = 76.501 (1)°	0.40 × 0.32 × 0.28 mm
V = 1296.1 (2) Å³

Data collection top

Siemens SMART CCD area-detector diffractometer	4491 independent reflections
Radiation source: fine-focus sealed tube	2244 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ω scans	θ_max = 25.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.955, T_max = 0.968	k = −13→15
6817 measured reflections	l = −16→16

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)] = 0.072	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.231	H-atom parameters constrained
S = 0.96	w = 1/[σ²(F_o²) + (0.1234P)²] where P = (F_o² + 2F_c²)/3
4491 reflections	(Δ/σ)_max < 0.001
363 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₅H₁₂F₂O₃	γ = 76.501 (1)°
M_r = 278.25	V = 1296.1 (2) Å³
Triclinic, P1	Z = 4
a = 7.4220 (8) Å	Mo Kα radiation
b = 13.0329 (14) Å	µ = 0.12 mm⁻¹
c = 14.1171 (16) Å	T = 298 K
α = 83.921 (2)°	0.40 × 0.32 × 0.28 mm
β = 77.913 (1)°

Data collection top

Siemens SMART CCD area-detector diffractometer	4491 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2244 reflections with I > 2σ(I)
T_min = 0.955, T_max = 0.968	R_int = 0.036
6817 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.072	0 restraints
wR(F²) = 0.231	H-atom parameters constrained
S = 0.96	Δρ_max = 0.27 e Å⁻³
4491 reflections	Δρ_min = −0.22 e Å⁻³
363 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
F1	1.1302 (5)	−0.2012 (2)	−0.40710 (17)	0.1012 (10)
F2	1.0857 (4)	0.1549 (2)	−0.36867 (17)	0.0938 (10)
O1	0.3966 (4)	−0.0294 (2)	0.39116 (18)	0.0685 (9)
O2	0.5359 (4)	−0.1407 (2)	0.24593 (18)	0.0660 (9)
H2	0.4839	−0.1278	0.3020	0.099*
O3	0.7935 (4)	0.0311 (2)	−0.04745 (16)	0.0550 (8)
C1	0.3850 (7)	0.1531 (3)	0.3919 (3)	0.0710 (13)
H1A	0.3360	0.1414	0.4597	0.106*
H1B	0.2913	0.2023	0.3626	0.106*
H1C	0.4958	0.1815	0.3844	0.106*
C2	0.4350 (6)	0.0503 (3)	0.3436 (3)	0.0537 (10)
C3	0.5232 (5)	0.0463 (3)	0.2413 (2)	0.0429 (9)
C4	0.5740 (5)	−0.0511 (3)	0.1963 (2)	0.0450 (9)
C5	0.6623 (5)	−0.0580 (3)	0.1002 (2)	0.0457 (9)
H5A	0.6932	−0.1227	0.0719	0.055*
C6	0.7044 (5)	0.0296 (3)	0.0468 (2)	0.0425 (9)
C7	0.6561 (5)	0.1271 (3)	0.0888 (2)	0.0499 (10)
H7	0.6832	0.1871	0.0522	0.060*
C8	0.5688 (5)	0.1336 (3)	0.1839 (2)	0.0486 (10)
H8	0.5387	0.1987	0.2113	0.058*
C9	0.8450 (6)	−0.0657 (3)	−0.0942 (2)	0.0511 (10)
H9A	0.7336	−0.0936	−0.0915	0.061*
H9B	0.9319	−0.1171	−0.0610	0.061*
C10	0.9362 (5)	−0.0474 (3)	−0.1973 (2)	0.0453 (9)
C11	0.9919 (6)	−0.1327 (3)	−0.2559 (3)	0.0585 (11)
H11	0.9724	−0.1990	−0.2309	0.070*
C12	1.0756 (6)	−0.1181 (4)	−0.3505 (3)	0.0630 (12)
C13	1.1114 (6)	−0.0235 (4)	−0.3913 (3)	0.0592 (11)
H13	1.1714	−0.0155	−0.4556	0.071*
C14	1.0529 (6)	0.0592 (3)	−0.3312 (3)	0.0582 (11)
C15	0.9681 (6)	0.0493 (3)	−0.2359 (3)	0.0543 (10)
H15	0.9327	0.1073	−0.1978	0.065*
F3	−0.1980 (4)	0.6542 (2)	0.85834 (18)	0.1013 (10)
F4	−0.0009 (4)	0.2932 (2)	0.93069 (17)	0.0972 (10)
O4	0.6255 (5)	0.4794 (2)	0.11718 (18)	0.0730 (9)
O5	0.5718 (4)	0.3646 (2)	0.27167 (18)	0.0697 (9)
H5	0.6143	0.3793	0.2147	0.104*
O6	0.1814 (4)	0.5295 (2)	0.55010 (16)	0.0569 (8)
C16	0.4955 (7)	0.6621 (4)	0.1001 (3)	0.0734 (14)
H16A	0.5610	0.6523	0.0343	0.110*
H16B	0.5433	0.7121	0.1277	0.110*
H16C	0.3630	0.6883	0.1010	0.110*
C17	0.5250 (6)	0.5590 (3)	0.1580 (3)	0.0551 (11)
C18	0.4401 (5)	0.5514 (3)	0.2605 (2)	0.0426 (9)
C19	0.4657 (6)	0.4531 (3)	0.3139 (2)	0.0487 (10)
C20	0.3820 (5)	0.4430 (3)	0.4103 (2)	0.0476 (10)
H20	0.3995	0.3774	0.4441	0.057*
C21	0.2719 (5)	0.5314 (3)	0.4563 (2)	0.0425 (9)
C22	0.2473 (6)	0.6292 (3)	0.4062 (2)	0.0519 (10)
H22	0.1748	0.6886	0.4377	0.062*
C23	0.3298 (5)	0.6385 (3)	0.3104 (2)	0.0501 (10)
H23	0.3119	0.7047	0.2775	0.060*
C24	0.2003 (6)	0.4312 (3)	0.6062 (2)	0.0500 (10)
H24A	0.3325	0.4014	0.6070	0.060*
H24B	0.1513	0.3818	0.5772	0.060*
C25	0.0940 (5)	0.4486 (3)	0.7071 (2)	0.0452 (9)
C26	−0.0051 (6)	0.5473 (3)	0.7369 (3)	0.0533 (10)
H26	−0.0067	0.6063	0.6936	0.064*
C27	−0.1003 (6)	0.5569 (3)	0.8303 (3)	0.0602 (12)
C28	−0.1032 (6)	0.4739 (3)	0.8982 (3)	0.0573 (11)
H28	−0.1689	0.4821	0.9616	0.069*
C29	−0.0026 (6)	0.3781 (3)	0.8659 (3)	0.0575 (11)
C30	0.0951 (6)	0.3632 (3)	0.7736 (3)	0.0564 (11)
H30	0.1619	0.2962	0.7556	0.068*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.142 (3)	0.099 (2)	0.0589 (15)	−0.0326 (19)	0.0144 (17)	−0.0386 (15)
F2	0.127 (3)	0.0745 (19)	0.0608 (16)	−0.0203 (17)	0.0172 (16)	0.0074 (14)
O1	0.083 (2)	0.070 (2)	0.0420 (15)	−0.0189 (17)	0.0142 (15)	−0.0045 (14)
O2	0.090 (2)	0.0521 (18)	0.0466 (15)	−0.0224 (16)	0.0132 (15)	0.0016 (13)
O3	0.0694 (19)	0.0644 (18)	0.0293 (13)	−0.0207 (15)	0.0041 (13)	−0.0077 (12)
C1	0.086 (3)	0.074 (3)	0.049 (2)	−0.019 (3)	0.007 (2)	−0.022 (2)
C2	0.056 (3)	0.062 (3)	0.039 (2)	−0.015 (2)	0.0019 (19)	−0.005 (2)
C3	0.043 (2)	0.051 (2)	0.0352 (19)	−0.0133 (18)	−0.0034 (17)	−0.0077 (17)
C4	0.043 (2)	0.052 (2)	0.037 (2)	−0.0114 (18)	−0.0008 (17)	0.0014 (18)
C5	0.047 (2)	0.051 (2)	0.036 (2)	−0.0091 (18)	−0.0026 (18)	−0.0065 (18)
C6	0.041 (2)	0.054 (2)	0.0288 (18)	−0.0096 (18)	0.0004 (16)	−0.0030 (17)
C7	0.064 (3)	0.047 (2)	0.037 (2)	−0.018 (2)	−0.0015 (19)	0.0012 (18)
C8	0.053 (2)	0.046 (2)	0.043 (2)	−0.0099 (18)	−0.0010 (19)	−0.0058 (17)
C9	0.057 (3)	0.061 (3)	0.0338 (19)	−0.015 (2)	−0.0017 (18)	−0.0044 (19)
C10	0.041 (2)	0.061 (3)	0.0335 (19)	−0.0099 (19)	−0.0082 (17)	−0.0045 (18)
C11	0.066 (3)	0.069 (3)	0.041 (2)	−0.023 (2)	0.002 (2)	−0.013 (2)
C12	0.067 (3)	0.077 (3)	0.048 (2)	−0.015 (2)	−0.005 (2)	−0.028 (2)
C13	0.054 (3)	0.085 (3)	0.034 (2)	−0.011 (2)	0.0031 (19)	−0.011 (2)
C14	0.058 (3)	0.067 (3)	0.041 (2)	−0.010 (2)	−0.001 (2)	0.009 (2)
C15	0.054 (3)	0.065 (3)	0.038 (2)	−0.006 (2)	−0.0040 (19)	−0.0027 (19)
F3	0.135 (3)	0.0683 (19)	0.0704 (17)	−0.0089 (17)	0.0385 (17)	−0.0170 (14)
F4	0.118 (2)	0.0870 (19)	0.0553 (15)	0.0010 (16)	0.0135 (15)	0.0235 (14)
O4	0.091 (2)	0.078 (2)	0.0414 (16)	−0.0216 (18)	0.0155 (16)	−0.0122 (15)
O5	0.094 (2)	0.0533 (18)	0.0471 (16)	−0.0092 (16)	0.0153 (16)	−0.0126 (14)
O6	0.0694 (19)	0.0613 (18)	0.0321 (13)	−0.0113 (14)	0.0052 (13)	−0.0041 (13)
C16	0.090 (4)	0.081 (3)	0.044 (2)	−0.025 (3)	−0.002 (2)	0.010 (2)
C17	0.059 (3)	0.068 (3)	0.040 (2)	−0.023 (2)	−0.002 (2)	−0.005 (2)
C18	0.047 (2)	0.050 (2)	0.0326 (18)	−0.0149 (18)	−0.0043 (17)	−0.0038 (17)
C19	0.057 (3)	0.052 (2)	0.037 (2)	−0.018 (2)	−0.0007 (18)	−0.0101 (19)
C20	0.059 (3)	0.050 (2)	0.0332 (19)	−0.018 (2)	−0.0017 (18)	−0.0015 (17)
C21	0.048 (2)	0.052 (2)	0.0277 (18)	−0.0162 (19)	−0.0014 (16)	−0.0039 (17)
C22	0.057 (3)	0.053 (3)	0.041 (2)	−0.0044 (19)	−0.0054 (19)	−0.0074 (18)
C23	0.057 (3)	0.049 (2)	0.041 (2)	−0.0092 (19)	−0.0043 (19)	−0.0008 (18)
C24	0.057 (3)	0.057 (3)	0.035 (2)	−0.016 (2)	−0.0040 (18)	−0.0013 (18)
C25	0.040 (2)	0.063 (3)	0.0336 (19)	−0.0141 (19)	−0.0031 (16)	−0.0079 (18)
C26	0.064 (3)	0.055 (3)	0.038 (2)	−0.017 (2)	0.002 (2)	0.0002 (19)
C27	0.070 (3)	0.051 (3)	0.050 (2)	−0.011 (2)	0.010 (2)	−0.010 (2)
C28	0.060 (3)	0.076 (3)	0.032 (2)	−0.015 (2)	0.0041 (19)	−0.008 (2)
C29	0.065 (3)	0.063 (3)	0.038 (2)	−0.012 (2)	−0.005 (2)	0.012 (2)
C30	0.060 (3)	0.060 (3)	0.042 (2)	−0.006 (2)	−0.004 (2)	0.000 (2)

Geometric parameters (Å, º) top

F1—C12	1.349 (4)	F3—C27	1.358 (5)
F2—C14	1.357 (4)	F4—C29	1.358 (4)
O1—C2	1.234 (4)	O4—C17	1.245 (5)
O2—C4	1.353 (4)	O5—C19	1.352 (4)
O2—H2	0.8207	O5—H5	0.8205
O3—C6	1.356 (4)	O6—C21	1.354 (4)
O3—C9	1.421 (4)	O6—C24	1.426 (4)
C1—C2	1.501 (5)	C16—C17	1.491 (5)
C1—H1A	0.9600	C16—H16A	0.9600
C1—H1B	0.9600	C16—H16B	0.9600
C1—H1C	0.9600	C16—H16C	0.9600
C2—C3	1.456 (5)	C17—C18	1.456 (5)
C3—C8	1.391 (5)	C18—C23	1.396 (5)
C3—C4	1.416 (5)	C18—C19	1.410 (5)
C4—C5	1.380 (4)	C19—C20	1.379 (5)
C5—C6	1.362 (5)	C20—C21	1.383 (5)
C5—H5A	0.9300	C20—H20	0.9300
C6—C7	1.397 (5)	C21—C22	1.383 (5)
C7—C8	1.366 (4)	C22—C23	1.369 (5)
C7—H7	0.9300	C22—H22	0.9300
C8—H8	0.9300	C23—H23	0.9300
C9—C10	1.492 (5)	C24—C25	1.490 (4)
C9—H9A	0.9700	C24—H24A	0.9700
C9—H9B	0.9700	C24—H24B	0.9700
C10—C15	1.371 (5)	C25—C30	1.376 (5)
C10—C11	1.387 (5)	C25—C26	1.384 (5)
C11—C12	1.364 (5)	C26—C27	1.362 (5)
C11—H11	0.9300	C26—H26	0.9300
C12—C13	1.364 (5)	C27—C28	1.368 (5)
C13—C14	1.375 (5)	C28—C29	1.367 (6)
C13—H13	0.9300	C28—H28	0.9300
C14—C15	1.367 (5)	C29—C30	1.362 (5)
C15—H15	0.9300	C30—H30	0.9300

C4—O2—H2	109.6	C19—O5—H5	109.6
C6—O3—C9	117.5 (3)	C21—O6—C24	118.8 (3)
C2—C1—H1A	109.5	C17—C16—H16A	109.5
C2—C1—H1B	109.5	C17—C16—H16B	109.5
H1A—C1—H1B	109.5	H16A—C16—H16B	109.5
C2—C1—H1C	109.5	C17—C16—H16C	109.5
H1A—C1—H1C	109.5	H16A—C16—H16C	109.5
H1B—C1—H1C	109.5	H16B—C16—H16C	109.5
O1—C2—C3	120.9 (4)	O4—C17—C18	120.3 (4)
O1—C2—C1	119.1 (3)	O4—C17—C16	118.8 (3)
C3—C2—C1	120.0 (4)	C18—C17—C16	120.9 (4)
C8—C3—C4	116.5 (3)	C23—C18—C19	116.9 (3)
C8—C3—C2	123.5 (3)	C23—C18—C17	122.7 (4)
C4—C3—C2	119.9 (3)	C19—C18—C17	120.3 (4)
O2—C4—C5	117.6 (3)	O5—C19—C20	117.6 (4)
O2—C4—C3	121.1 (3)	O5—C19—C18	120.9 (3)
C5—C4—C3	121.3 (3)	C20—C19—C18	121.5 (4)
C6—C5—C4	120.2 (3)	C19—C20—C21	119.5 (4)
C6—C5—H5A	119.9	C19—C20—H20	120.2
C4—C5—H5A	119.9	C21—C20—H20	120.2
O3—C6—C5	124.9 (3)	O6—C21—C20	124.0 (3)
O3—C6—C7	115.0 (3)	O6—C21—C22	115.8 (3)
C5—C6—C7	120.1 (3)	C20—C21—C22	120.2 (3)
C8—C7—C6	119.6 (3)	C23—C22—C21	120.0 (4)
C8—C7—H7	120.2	C23—C22—H22	120.0
C6—C7—H7	120.2	C21—C22—H22	120.0
C7—C8—C3	122.4 (3)	C22—C23—C18	121.8 (4)
C7—C8—H8	118.8	C22—C23—H23	119.1
C3—C8—H8	118.8	C18—C23—H23	119.1
O3—C9—C10	109.5 (3)	O6—C24—C25	109.5 (3)
O3—C9—H9A	109.8	O6—C24—H24A	109.8
C10—C9—H9A	109.8	C25—C24—H24A	109.8
O3—C9—H9B	109.8	O6—C24—H24B	109.8
C10—C9—H9B	109.8	C25—C24—H24B	109.8
H9A—C9—H9B	108.2	H24A—C24—H24B	108.2
C15—C10—C11	119.1 (3)	C30—C25—C26	118.7 (3)
C15—C10—C9	122.8 (3)	C30—C25—C24	118.8 (4)
C11—C10—C9	118.1 (3)	C26—C25—C24	122.5 (3)
C12—C11—C10	119.2 (4)	C27—C26—C25	119.3 (4)
C12—C11—H11	120.4	C27—C26—H26	120.4
C10—C11—H11	120.4	C25—C26—H26	120.4
F1—C12—C11	119.1 (4)	F3—C27—C26	118.6 (4)
F1—C12—C13	117.5 (4)	F3—C27—C28	117.7 (3)
C11—C12—C13	123.4 (4)	C26—C27—C28	123.7 (4)
C12—C13—C14	115.6 (3)	C29—C28—C27	115.1 (3)
C12—C13—H13	122.2	C29—C28—H28	122.4
C14—C13—H13	122.2	C27—C28—H28	122.4
F2—C14—C15	118.8 (4)	F4—C29—C30	118.7 (4)
F2—C14—C13	117.7 (3)	F4—C29—C28	117.4 (3)
C15—C14—C13	123.5 (4)	C30—C29—C28	124.0 (4)
C14—C15—C10	119.1 (4)	C29—C30—C25	119.2 (4)
C14—C15—H15	120.5	C29—C30—H30	120.4
C10—C15—H15	120.5	C25—C30—H30	120.4

O1—C2—C3—C8	179.7 (4)	O4—C17—C18—C23	178.5 (4)
C1—C2—C3—C8	1.2 (6)	C16—C17—C18—C23	−0.8 (6)
O1—C2—C3—C4	−2.9 (6)	O4—C17—C18—C19	−2.0 (6)
C1—C2—C3—C4	178.6 (4)	C16—C17—C18—C19	178.6 (4)
C8—C3—C4—O2	180.0 (3)	C23—C18—C19—O5	−179.4 (3)
C2—C3—C4—O2	2.4 (5)	C17—C18—C19—O5	1.2 (6)
C8—C3—C4—C5	−0.7 (5)	C23—C18—C19—C20	1.5 (5)
C2—C3—C4—C5	−178.2 (3)	C17—C18—C19—C20	−178.0 (3)
O2—C4—C5—C6	−179.9 (3)	O5—C19—C20—C21	−179.9 (3)
C3—C4—C5—C6	0.7 (6)	C18—C19—C20—C21	−0.7 (6)
C9—O3—C6—C5	0.7 (5)	C24—O6—C21—C20	0.5 (5)
C9—O3—C6—C7	−179.6 (3)	C24—O6—C21—C22	179.9 (3)
C4—C5—C6—O3	178.9 (3)	C19—C20—C21—O6	178.9 (3)
C4—C5—C6—C7	−0.8 (5)	C19—C20—C21—C22	−0.6 (6)
O3—C6—C7—C8	−178.9 (3)	O6—C21—C22—C23	−178.5 (3)
C5—C6—C7—C8	0.8 (6)	C20—C21—C22—C23	1.0 (6)
C6—C7—C8—C3	−0.8 (6)	C21—C22—C23—C18	−0.1 (6)
C4—C3—C8—C7	0.7 (5)	C19—C18—C23—C22	−1.1 (5)
C2—C3—C8—C7	178.2 (4)	C17—C18—C23—C22	178.4 (4)
C6—O3—C9—C10	178.5 (3)	C21—O6—C24—C25	178.4 (3)
O3—C9—C10—C15	2.3 (5)	O6—C24—C25—C30	−179.6 (3)
O3—C9—C10—C11	−178.3 (3)	O6—C24—C25—C26	0.1 (5)
C15—C10—C11—C12	−0.5 (6)	C30—C25—C26—C27	−0.9 (6)
C9—C10—C11—C12	−180.0 (4)	C24—C25—C26—C27	179.5 (4)
C10—C11—C12—F1	179.8 (4)	C25—C26—C27—F3	−179.6 (4)
C10—C11—C12—C13	1.2 (7)	C25—C26—C27—C28	0.5 (7)
F1—C12—C13—C14	179.8 (4)	F3—C27—C28—C29	−180.0 (4)
C11—C12—C13—C14	−1.6 (6)	C26—C27—C28—C29	−0.1 (7)
C12—C13—C14—F2	179.9 (4)	C27—C28—C29—F4	179.9 (4)
C12—C13—C14—C15	1.5 (6)	C27—C28—C29—C30	0.0 (6)
F2—C14—C15—C10	−179.4 (4)	F4—C29—C30—C25	179.7 (4)
C13—C14—C15—C10	−1.0 (6)	C28—C29—C30—C25	−0.3 (7)
C11—C10—C15—C14	0.5 (6)	C26—C25—C30—C29	0.8 (6)
C9—C10—C15—C14	179.9 (4)	C24—C25—C30—C29	−179.6 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.82	1.81	2.533 (4)	147
O5—H5···O4	0.82	1.80	2.525 (4)	147
C8—H8···O5	0.93	2.49	3.382 (5)	161
C13—H13···O1ⁱ	0.93	2.44	3.342 (5)	165
C28—H28···O4ⁱⁱ	0.93	2.40	3.315 (5)	168

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₂F₂O₃
M_r	278.25
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	7.4220 (8), 13.0329 (14), 14.1171 (16)
α, β, γ (°)	83.921 (2), 77.913 (1), 76.501 (1)
V (Å³)	1296.1 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.40 × 0.32 × 0.28

Data collection
Diffractometer	Siemens SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.955, 0.968
No. of measured, independent and observed [I > 2σ(I)] reflections	6817, 4491, 2244
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.072, 0.231, 0.96
No. of reflections	4491
No. of parameters	363
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.22

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), 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—H2···O1	0.82	1.81	2.533 (4)	146.9
O5—H5···O4	0.82	1.80	2.525 (4)	147.3
C8—H8···O5	0.93	2.49	3.382 (5)	161.3
C13—H13···O1ⁱ	0.93	2.44	3.342 (5)	164.6
C28—H28···O4ⁱⁱ	0.93	2.40	3.315 (5)	168.2

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

Acknowledgements

We would like to acknowledge funding support from the National Natural Science Foundation of China (grant No. 30971882) and the Program of Natural Science Basic Research in Shaanxi (No. 2009JM3010).

References

Dermer, O. C. (1934). Chem. Rev. 14, 385–430. CrossRef CAS Google Scholar
Ma, Y.-T., Wang, J.-J., Liu, X.-W., Yang, S.-X. & Gao, J.-M. (2010). Acta Cryst. E66, o52. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar