(E)-1-(3,5-Difluoro-phen-yl)-3-(2,4-dimeth-oxy-phen-yl)prop-2-en-1-one.

The title compound, C(17)H(14)F(2)O(3), is approximately planar, the dihedral angle between the rings being 5.46 (2)°. The H atoms of the central propenone group are trans. The crystal structure is stabilized by inter-molecular C-H⋯F hydrogen bonds.

Related literature

For related structures, see: Peng et al. (2010 ▶); Wu, Zhang et al. (2009 ▶); Liang et al. (2007 ▶); Yathirajan et al. (2006 ▶). For background to and applications of chalcones, see: Nowakowska (2007 ▶); Nielsen et al. (2005 ▶); Wu, Qiu et al. (2009 ▶); Liang et al. (2009 ▶); Mojzisa et al. (2008 ▶); Liu et al. (2008 ▶); Wu et al. (2010 ▶); Zhao et al. (2010 ▶); Selvakumar et al. (2007 ▶).

Experimental

Crystal data

C17H14F2O3

M = 304.28

Triclinic,

a = 7.8047 (8) Å

b = 11.2591 (12) Å

c = 17.0080 (18) Å

α = 81.407 (2)°

β = 81.231 (2)°

γ = 76.319 (2)°

V = 1425.1 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.27 × 0.22 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.602, T max = 1.000

7600 measured reflections

5242 independent reflections

2815 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.162

S = 0.92

5242 reflections

401 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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/S1600536810035257/pb2039sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810035257/pb2039Isup2.hkl

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

C17H14F2O3	Z = 4
Mr = 304.28	F(000) = 632
Triclinic, P1	Dx = 1.418 Mg m−3
a = 7.8047 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.2591 (12) Å	Cell parameters from 1503 reflections
c = 17.0080 (18) Å	θ = 4.7–46.3°
α = 81.407 (2)°	µ = 0.11 mm−1
β = 81.231 (2)°	T = 293 K
γ = 76.319 (2)°	Prismatic, green
V = 1425.1 (3) Å3	0.27 × 0.22 × 0.17 mm

Bruker SMART CCD area-detector diffractometer	5242 independent reflections
Radiation source: fine-focus sealed tube	2815 reflections with I > 2σ(I)
graphite	Rint = 0.034
phi and ω scans	θmax = 25.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.602, Tmax = 1.000	k = −6→13
7600 measured reflections	l = −20→20

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.162	H-atom parameters constrained
S = 0.92	w = 1/[σ2(Fo2) + (0.0748P)2] where P = (Fo2 + 2Fc2)/3
5242 reflections	(Δ/σ)max = 0.005
401 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.20 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	−0.1189 (2)	0.41876 (16)	1.15514 (9)	0.0680 (5)
F2	−0.4957 (2)	0.73654 (16)	1.01469 (11)	0.0774 (6)
F3	−0.1962 (3)	0.85773 (17)	0.95482 (10)	0.0765 (6)
F4	−0.5094 (3)	1.19504 (18)	0.80248 (13)	0.1043 (8)
O1	−0.2308 (3)	0.4469 (2)	0.81479 (12)	0.0796 (8)
O2	0.0468 (3)	0.10719 (18)	0.67405 (11)	0.0612 (6)
O3	0.4032 (3)	−0.26852 (18)	0.79562 (12)	0.0638 (6)
O4	−0.2520 (3)	0.8979 (2)	0.60758 (13)	0.0763 (7)
O5	0.1805 (3)	0.61876 (18)	0.46058 (11)	0.0595 (6)
O6	0.4537 (3)	0.21210 (18)	0.57760 (12)	0.0621 (6)
C1	−0.1733 (4)	0.3926 (3)	0.87639 (17)	0.0503 (8)
C2	−0.0645 (4)	0.2671 (3)	0.87879 (17)	0.0534 (8)
H2	−0.0239	0.2287	0.9269	0.064*
C3	−0.0216 (4)	0.2062 (3)	0.81555 (17)	0.0478 (8)
H3	−0.0661	0.2473	0.7688	0.057*
C4	0.0863 (4)	0.0833 (3)	0.81000 (16)	0.0433 (7)
C5	0.1221 (4)	0.0337 (3)	0.73634 (16)	0.0469 (7)
C6	0.2271 (4)	−0.0839 (3)	0.72881 (17)	0.0494 (8)
H6	0.2496	−0.1154	0.6798	0.059*
C7	0.2975 (4)	−0.1533 (3)	0.79590 (18)	0.0492 (8)
C8	0.2621 (4)	−0.1065 (3)	0.86926 (18)	0.0580 (9)
H8	0.3096	−0.1533	0.9139	0.070*
C9	0.1576 (4)	0.0082 (3)	0.87555 (17)	0.0525 (8)
H9	0.1329	0.0374	0.9253	0.063*
C10	−0.2167 (3)	0.4558 (2)	0.95157 (16)	0.0418 (7)
C11	−0.1461 (4)	0.4034 (3)	1.02204 (16)	0.0457 (7)
H11	−0.0681	0.3269	1.0249	0.055*
C12	−0.1941 (4)	0.4671 (3)	1.08689 (16)	0.0473 (7)
C13	−0.3090 (4)	0.5794 (3)	1.08698 (18)	0.0537 (8)
H13	−0.3390	0.6210	1.1321	0.064*
C14	−0.3774 (4)	0.6268 (3)	1.01672 (18)	0.0503 (8)
C15	−0.3339 (4)	0.5702 (3)	0.94908 (17)	0.0484 (8)
H15	−0.3814	0.6070	0.9022	0.058*
C16	0.0892 (5)	0.0699 (3)	0.59549 (16)	0.0703 (10)
H16A	0.2140	0.0624	0.5787	0.105*
H16B	0.0229	0.1302	0.5589	0.105*
H16C	0.0590	−0.0081	0.5960	0.105*
C17	0.4356 (4)	−0.3267 (3)	0.72383 (19)	0.0662 (9)
H17A	0.3244	−0.3278	0.7067	0.099*
H17B	0.5025	−0.4096	0.7340	0.099*
H17C	0.5018	−0.2817	0.6826	0.099*
C18	−0.2005 (4)	0.8425 (3)	0.67020 (17)	0.0487 (8)
C19	−0.0831 (4)	0.7203 (3)	0.67198 (17)	0.0493 (8)
H19	−0.0649	0.6735	0.7211	0.059*
C20	−0.0021 (4)	0.6746 (3)	0.60528 (17)	0.0466 (7)
H20	−0.0241	0.7249	0.5577	0.056*
C21	0.1172 (4)	0.5552 (2)	0.59737 (16)	0.0423 (7)
C22	0.2083 (3)	0.5271 (3)	0.52183 (16)	0.0430 (7)
C23	0.3202 (3)	0.4129 (2)	0.51277 (16)	0.0467 (7)
H23	0.3787	0.3950	0.4626	0.056*
C24	0.3438 (4)	0.3257 (3)	0.57915 (17)	0.0465 (7)
C25	0.2562 (4)	0.3512 (3)	0.65383 (17)	0.0521 (8)
H25	0.2723	0.2921	0.6981	0.062*
C26	0.1461 (4)	0.4637 (3)	0.66228 (16)	0.0478 (7)
H26	0.0885	0.4800	0.7128	0.057*
C27	−0.2562 (4)	0.9035 (3)	0.74549 (17)	0.0440 (7)
C28	−0.2002 (4)	0.8479 (3)	0.81899 (17)	0.0496 (8)
H28	−0.1295	0.7687	0.8238	0.060*
C29	−0.2513 (4)	0.9119 (3)	0.88340 (17)	0.0500 (8)
C30	−0.3563 (4)	1.0274 (3)	0.88054 (19)	0.0579 (8)
H30	−0.3918	1.0683	0.9259	0.070*
C31	−0.4070 (4)	1.0801 (3)	0.8076 (2)	0.0605 (9)
C32	−0.3603 (4)	1.0222 (3)	0.74061 (19)	0.0562 (8)
H32	−0.3975	1.0615	0.6921	0.067*
C33	0.2640 (4)	0.5973 (3)	0.38187 (16)	0.0594 (9)
H33A	0.3906	0.5764	0.3817	0.089*
H33B	0.2316	0.6703	0.3454	0.089*
H33C	0.2259	0.5307	0.3655	0.089*
C34	0.5535 (4)	0.1789 (3)	0.50357 (19)	0.0704 (10)
H34A	0.4738	0.1760	0.4665	0.106*
H34B	0.6313	0.0996	0.5126	0.106*
H34C	0.6226	0.2390	0.4818	0.106*

	U11	U22	U33	U12	U13	U23
F1	0.0799 (13)	0.0739 (13)	0.0421 (10)	0.0071 (10)	−0.0177 (9)	−0.0090 (9)
F2	0.0863 (14)	0.0563 (12)	0.0775 (13)	0.0256 (10)	−0.0236 (10)	−0.0218 (10)
F3	0.1055 (15)	0.0721 (13)	0.0443 (11)	0.0041 (11)	−0.0221 (10)	−0.0078 (9)
F4	0.139 (2)	0.0618 (13)	0.0955 (16)	0.0442 (13)	−0.0455 (14)	−0.0312 (12)
O1	0.1074 (19)	0.0692 (16)	0.0395 (13)	0.0305 (14)	−0.0166 (12)	−0.0070 (12)
O2	0.0856 (16)	0.0512 (13)	0.0334 (11)	0.0128 (11)	−0.0118 (10)	−0.0025 (10)
O3	0.0758 (15)	0.0462 (13)	0.0605 (14)	0.0126 (11)	−0.0208 (12)	−0.0074 (11)
O4	0.1063 (19)	0.0609 (15)	0.0495 (14)	0.0189 (13)	−0.0280 (13)	−0.0088 (11)
O5	0.0801 (15)	0.0510 (12)	0.0341 (11)	0.0040 (11)	−0.0019 (10)	0.0025 (10)
O6	0.0730 (15)	0.0514 (13)	0.0475 (13)	0.0146 (11)	−0.0073 (11)	−0.0057 (10)
C1	0.0553 (19)	0.0490 (19)	0.0368 (17)	0.0027 (15)	−0.0018 (14)	−0.0004 (14)
C2	0.063 (2)	0.0495 (18)	0.0396 (17)	0.0054 (16)	−0.0091 (14)	−0.0046 (14)
C3	0.0543 (19)	0.0489 (18)	0.0365 (16)	−0.0023 (15)	−0.0075 (13)	−0.0055 (14)
C4	0.0500 (18)	0.0413 (17)	0.0366 (16)	−0.0054 (14)	−0.0070 (13)	−0.0040 (13)
C5	0.0531 (18)	0.0441 (18)	0.0386 (16)	−0.0035 (15)	−0.0053 (13)	−0.0015 (14)
C6	0.0569 (19)	0.0477 (18)	0.0394 (17)	−0.0003 (15)	−0.0050 (14)	−0.0110 (14)
C7	0.0487 (18)	0.0431 (18)	0.0501 (19)	0.0019 (15)	−0.0093 (14)	−0.0033 (15)
C8	0.071 (2)	0.054 (2)	0.0457 (19)	0.0014 (17)	−0.0218 (16)	−0.0033 (16)
C9	0.064 (2)	0.053 (2)	0.0399 (17)	−0.0030 (17)	−0.0128 (15)	−0.0118 (15)
C10	0.0419 (16)	0.0432 (17)	0.0381 (16)	−0.0067 (14)	−0.0013 (12)	−0.0058 (13)
C11	0.0475 (18)	0.0434 (18)	0.0415 (17)	−0.0024 (14)	−0.0048 (13)	−0.0030 (14)
C12	0.0502 (18)	0.0518 (19)	0.0361 (16)	−0.0011 (15)	−0.0101 (14)	−0.0048 (14)
C13	0.057 (2)	0.057 (2)	0.0455 (18)	−0.0047 (17)	−0.0027 (15)	−0.0164 (15)
C14	0.0508 (18)	0.0411 (18)	0.0532 (19)	0.0047 (15)	−0.0058 (15)	−0.0113 (15)
C15	0.0526 (19)	0.0446 (18)	0.0447 (17)	−0.0018 (15)	−0.0106 (14)	−0.0042 (14)
C16	0.108 (3)	0.062 (2)	0.0320 (17)	−0.002 (2)	−0.0128 (17)	−0.0012 (16)
C17	0.075 (2)	0.056 (2)	0.061 (2)	0.0025 (18)	−0.0060 (17)	−0.0159 (17)
C18	0.0531 (19)	0.0466 (18)	0.0455 (18)	−0.0039 (15)	−0.0170 (15)	−0.0028 (15)
C19	0.0575 (19)	0.0464 (18)	0.0402 (17)	0.0019 (15)	−0.0135 (14)	−0.0064 (14)
C20	0.0535 (18)	0.0468 (18)	0.0393 (17)	−0.0069 (15)	−0.0115 (14)	−0.0055 (14)
C21	0.0447 (17)	0.0410 (17)	0.0409 (16)	−0.0057 (14)	−0.0089 (13)	−0.0063 (13)
C22	0.0467 (17)	0.0448 (18)	0.0368 (16)	−0.0072 (14)	−0.0093 (13)	−0.0029 (13)
C23	0.0511 (18)	0.0489 (18)	0.0361 (16)	−0.0026 (15)	−0.0041 (13)	−0.0074 (14)
C24	0.0471 (18)	0.0418 (18)	0.0463 (18)	0.0014 (14)	−0.0100 (14)	−0.0047 (14)
C25	0.0562 (19)	0.0504 (19)	0.0406 (17)	0.0029 (16)	−0.0095 (14)	0.0032 (14)
C26	0.0533 (18)	0.0527 (19)	0.0328 (15)	−0.0035 (15)	−0.0034 (13)	−0.0051 (14)
C27	0.0429 (17)	0.0414 (17)	0.0444 (17)	−0.0010 (14)	−0.0064 (13)	−0.0066 (13)
C28	0.0535 (19)	0.0431 (17)	0.0476 (18)	0.0018 (15)	−0.0099 (14)	−0.0068 (14)
C29	0.0552 (19)	0.0530 (19)	0.0394 (17)	−0.0035 (16)	−0.0105 (14)	−0.0068 (15)
C30	0.062 (2)	0.060 (2)	0.053 (2)	−0.0035 (17)	−0.0097 (16)	−0.0227 (17)
C31	0.064 (2)	0.0454 (19)	0.068 (2)	0.0114 (17)	−0.0215 (18)	−0.0176 (17)
C32	0.062 (2)	0.0478 (19)	0.0529 (19)	0.0042 (16)	−0.0196 (16)	−0.0022 (16)
C33	0.068 (2)	0.070 (2)	0.0328 (16)	−0.0052 (18)	−0.0047 (15)	0.0020 (15)
C34	0.079 (2)	0.062 (2)	0.058 (2)	0.0128 (19)	−0.0041 (18)	−0.0182 (18)

F1—C12	1.363 (3)	C15—H15	0.9300
F2—C14	1.355 (3)	C16—H16A	0.9600
F3—C29	1.359 (3)	C16—H16B	0.9600
F4—C31	1.349 (3)	C16—H16C	0.9600
O1—C1	1.223 (3)	C17—H17A	0.9600
O2—C5	1.360 (3)	C17—H17B	0.9600
O2—C16	1.428 (3)	C17—H17C	0.9600
O3—C7	1.363 (3)	C18—C19	1.461 (4)
O3—C17	1.432 (3)	C18—C27	1.501 (4)
O4—C18	1.224 (3)	C19—C20	1.324 (4)
O5—C22	1.356 (3)	C19—H19	0.9300
O5—C33	1.425 (3)	C20—C21	1.455 (4)
O6—C24	1.362 (3)	C20—H20	0.9300
O6—C34	1.427 (3)	C21—C26	1.399 (4)
C1—C2	1.465 (4)	C21—C22	1.412 (4)
C1—C10	1.510 (4)	C22—C23	1.388 (4)
C2—C3	1.319 (4)	C23—C24	1.385 (3)
C2—H2	0.9300	C23—H23	0.9300
C3—C4	1.448 (4)	C24—C25	1.384 (4)
C3—H3	0.9300	C25—C26	1.366 (4)
C4—C9	1.398 (4)	C25—H25	0.9300
C4—C5	1.410 (4)	C26—H26	0.9300
C5—C6	1.395 (4)	C27—C32	1.388 (4)
C6—C7	1.391 (4)	C27—C28	1.396 (4)
C6—H6	0.9300	C28—C29	1.358 (4)
C7—C8	1.390 (4)	C28—H28	0.9300
C8—C9	1.364 (4)	C29—C30	1.362 (4)
C8—H8	0.9300	C30—C31	1.365 (4)
C9—H9	0.9300	C30—H30	0.9300
C10—C11	1.387 (4)	C31—C32	1.357 (4)
C10—C15	1.391 (4)	C32—H32	0.9300
C11—C12	1.362 (4)	C33—H33A	0.9600
C11—H11	0.9300	C33—H33B	0.9600
C12—C13	1.366 (4)	C33—H33C	0.9600
C13—C14	1.366 (4)	C34—H34A	0.9600
C13—H13	0.9300	C34—H34B	0.9600
C14—C15	1.358 (4)	C34—H34C	0.9600
C5—O2—C16	119.8 (2)	H17A—C17—H17C	109.5
C7—O3—C17	118.9 (2)	H17B—C17—H17C	109.5
C22—O5—C33	119.3 (2)	O4—C18—C19	121.0 (3)
C24—O6—C34	119.0 (2)	O4—C18—C27	118.9 (3)
O1—C1—C2	121.2 (3)	C19—C18—C27	120.1 (2)
O1—C1—C10	119.4 (3)	C20—C19—C18	121.5 (3)
C2—C1—C10	119.4 (2)	C20—C19—H19	119.2
C3—C2—C1	122.7 (3)	C18—C19—H19	119.2
C3—C2—H2	118.6	C19—C20—C21	127.9 (3)
C1—C2—H2	118.6	C19—C20—H20	116.0
C2—C3—C4	128.0 (3)	C21—C20—H20	116.0
C2—C3—H3	116.0	C26—C21—C22	117.2 (2)
C4—C3—H3	116.0	C26—C21—C20	122.7 (3)
C9—C4—C5	116.9 (3)	C22—C21—C20	120.2 (3)
C9—C4—C3	122.9 (3)	O5—C22—C23	123.3 (3)
C5—C4—C3	120.2 (2)	O5—C22—C21	115.6 (2)
O2—C5—C6	122.7 (3)	C23—C22—C21	121.0 (3)
O2—C5—C4	115.8 (2)	C24—C23—C22	119.3 (3)
C6—C5—C4	121.6 (3)	C24—C23—H23	120.3
C7—C6—C5	118.8 (3)	C22—C23—H23	120.3
C7—C6—H6	120.6	O6—C24—C25	115.0 (2)
C5—C6—H6	120.6	O6—C24—C23	124.3 (3)
O3—C7—C8	115.4 (3)	C25—C24—C23	120.7 (3)
O3—C7—C6	124.1 (3)	C26—C25—C24	119.7 (3)
C8—C7—C6	120.5 (3)	C26—C25—H25	120.2
C9—C8—C7	119.8 (3)	C24—C25—H25	120.2
C9—C8—H8	120.1	C25—C26—C21	122.1 (3)
C7—C8—H8	120.1	C25—C26—H26	118.9
C8—C9—C4	122.4 (3)	C21—C26—H26	118.9
C8—C9—H9	118.8	C32—C27—C28	119.0 (3)
C4—C9—H9	118.8	C32—C27—C18	118.4 (3)
C11—C10—C15	119.6 (3)	C28—C27—C18	122.5 (3)
C11—C10—C1	122.6 (3)	C29—C28—C27	118.5 (3)
C15—C10—C1	117.8 (2)	C29—C28—H28	120.7
C12—C11—C10	118.3 (3)	C27—C28—H28	120.7
C12—C11—H11	120.9	C28—C29—F3	118.5 (3)
C10—C11—H11	120.9	C28—C29—C30	123.5 (3)
C11—C12—F1	118.5 (3)	F3—C29—C30	118.0 (3)
C11—C12—C13	123.9 (3)	C29—C30—C31	116.6 (3)
F1—C12—C13	117.6 (3)	C29—C30—H30	121.7
C12—C13—C14	116.0 (3)	C31—C30—H30	121.7
C12—C13—H13	122.0	F4—C31—C32	118.7 (3)
C14—C13—H13	122.0	F4—C31—C30	118.1 (3)
F2—C14—C15	118.3 (3)	C32—C31—C30	123.2 (3)
F2—C14—C13	118.0 (3)	C31—C32—C27	119.1 (3)
C15—C14—C13	123.7 (3)	C31—C32—H32	120.5
C14—C15—C10	118.5 (3)	C27—C32—H32	120.5
C14—C15—H15	120.8	O5—C33—H33A	109.5
C10—C15—H15	120.8	O5—C33—H33B	109.5
O2—C16—H16A	109.5	H33A—C33—H33B	109.5
O2—C16—H16B	109.5	O5—C33—H33C	109.5
H16A—C16—H16B	109.5	H33A—C33—H33C	109.5
O2—C16—H16C	109.5	H33B—C33—H33C	109.5
H16A—C16—H16C	109.5	O6—C34—H34A	109.5
H16B—C16—H16C	109.5	O6—C34—H34B	109.5
O3—C17—H17A	109.5	H34A—C34—H34B	109.5
O3—C17—H17B	109.5	O6—C34—H34C	109.5
H17A—C17—H17B	109.5	H34A—C34—H34C	109.5
O3—C17—H17C	109.5	H34B—C34—H34C	109.5
O1—C1—C2—C3	0.5 (5)	O4—C18—C19—C20	12.7 (5)
C10—C1—C2—C3	179.9 (3)	C27—C18—C19—C20	−165.8 (3)
C1—C2—C3—C4	179.1 (3)	C18—C19—C20—C21	−179.8 (3)
C2—C3—C4—C9	2.3 (5)	C19—C20—C21—C26	8.0 (5)
C2—C3—C4—C5	−178.4 (3)	C19—C20—C21—C22	−172.6 (3)
C16—O2—C5—C6	−6.5 (4)	C33—O5—C22—C23	2.4 (4)
C16—O2—C5—C4	174.0 (3)	C33—O5—C22—C21	−178.5 (2)
C9—C4—C5—O2	178.1 (3)	C26—C21—C22—O5	−178.5 (2)
C3—C4—C5—O2	−1.2 (4)	C20—C21—C22—O5	2.0 (4)
C9—C4—C5—C6	−1.4 (4)	C26—C21—C22—C23	0.6 (4)
C3—C4—C5—C6	179.3 (3)	C20—C21—C22—C23	−178.8 (3)
O2—C5—C6—C7	−179.4 (3)	O5—C22—C23—C24	178.5 (2)
C4—C5—C6—C7	0.1 (4)	C21—C22—C23—C24	−0.6 (4)
C17—O3—C7—C8	175.6 (3)	C34—O6—C24—C25	−178.2 (3)
C17—O3—C7—C6	−4.4 (4)	C34—O6—C24—C23	0.5 (4)
C5—C6—C7—O3	−179.3 (3)	C22—C23—C24—O6	−178.2 (3)
C5—C6—C7—C8	0.7 (4)	C22—C23—C24—C25	0.5 (4)
O3—C7—C8—C9	180.0 (3)	O6—C24—C25—C26	178.5 (3)
C6—C7—C8—C9	0.0 (5)	C23—C24—C25—C26	−0.3 (4)
C7—C8—C9—C4	−1.5 (5)	C24—C25—C26—C21	0.4 (5)
C5—C4—C9—C8	2.1 (4)	C22—C21—C26—C25	−0.5 (4)
C3—C4—C9—C8	−178.6 (3)	C20—C21—C26—C25	178.9 (3)
O1—C1—C10—C11	−175.4 (3)	O4—C18—C27—C32	−1.7 (4)
C2—C1—C10—C11	5.2 (4)	C19—C18—C27—C32	176.7 (3)
O1—C1—C10—C15	5.4 (4)	O4—C18—C27—C28	−178.6 (3)
C2—C1—C10—C15	−174.0 (3)	C19—C18—C27—C28	−0.1 (4)
C15—C10—C11—C12	−0.3 (4)	C32—C27—C28—C29	0.6 (4)
C1—C10—C11—C12	−179.6 (3)	C18—C27—C28—C29	177.4 (3)
C10—C11—C12—F1	−177.0 (2)	C27—C28—C29—F3	−179.8 (3)
C10—C11—C12—C13	0.6 (5)	C27—C28—C29—C30	0.8 (5)
C11—C12—C13—C14	0.3 (5)	C28—C29—C30—C31	−1.7 (5)
F1—C12—C13—C14	177.9 (3)	F3—C29—C30—C31	178.9 (3)
C12—C13—C14—F2	178.3 (3)	C29—C30—C31—F4	−179.2 (3)
C12—C13—C14—C15	−1.5 (5)	C29—C30—C31—C32	1.2 (5)
F2—C14—C15—C10	−178.1 (3)	F4—C31—C32—C27	−179.5 (3)
C13—C14—C15—C10	1.7 (5)	C30—C31—C32—C27	0.1 (5)
C11—C10—C15—C14	−0.7 (4)	C28—C27—C32—C31	−1.0 (5)
C1—C10—C15—C14	178.6 (3)	C18—C27—C32—C31	−177.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C25—H25···F4i	0.93	2.59	3.375 (3)	142
C13—H13···F4ii	0.93	2.46	3.303 (4)	151
C9—H9···F3iii	0.93	2.66	3.532 (3)	156
C30—H30···F2ii	0.93	2.47	3.303 (4)	149
C8—H8···F2i	0.93	2.46	3.369 (3)	166
C28—H28···F1iii	0.93	2.53	3.437 (3)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C25—H25⋯F4i	0.93	2.59	3.375 (3)	142
C13—H13⋯F4ii	0.93	2.46	3.303 (4)	151
C9—H9⋯F3iii	0.93	2.66	3.532 (3)	156
C30—H30⋯F2ii	0.93	2.47	3.303 (4)	149
C8—H8⋯F2i	0.93	2.46	3.369 (3)	166
C28—H28⋯F1iii	0.93	2.53	3.437 (3)	166

Symmetry codes: (i) ; (ii) ; (iii) .