1-[4-(3,5-Difluoro-benz-yloxy)-2-hy-droxy-phen-yl]ethanone.

The title compound, C(15)H(12)F(2)O(3), has been obtained by the reaction of 2,4-dihy-droxy-lacetonephenone, potassium carbonate and 3,5-difluoro-benzyl bromide. The hy-droxy group is involved in an intra-molecular O-H⋯O hydrogen bond in each of the two independent mol-ecules 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 inter-actions link the mol-ecules into tetra-meric 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 = 278.25

Triclinic,

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[F 2 > 2σ(F 2)] = 0.072

wR(F 2) = 0.231

S = 0.96

4491 reflections

363 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.22 e Å−3

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.

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810033787/bv2156Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C15H12F2O3	Z = 4
Mr = 278.25	F(000) = 576
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.1234P)2] where P = (Fo2 + 2Fc2)/3
4491 reflections	(Δ/σ)max < 0.001
363 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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.

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) ; (ii) .