(2E)-1-(2,6-Dichloro-3-fluoro-phen-yl)-3-(4-meth-oxy-phen-yl)prop-2-en-1-one.

There are two independent mol-ecules in the asymmetric unit of the title compound, C(16)H(11)Cl(2)FO(2). The F atom equally populates both meta positions of the 6-dichloro-3-fluoro-phenyl ring in each mol-ecule, resulting in 0.5 occupancy for both the F and H atoms in these positions. The dihedral angle between the mean planes of the benzene rings are 77.5 (2) and 89.8 (8)°in the two mol-ecules. In the crystal, weak C-H⋯F and C-H⋯O inter-actions involving the half-occupied H and F atoms are observed. Weak π-π stacking inter-actions [centroid-centroid distance = 3.150 (2) Å] also contribute to the crystal stability.

Related literature

For the pharmacological importance of chalcones, see: Dominguez et al. (2001 ▶); Li et al. (1995 ▶); Mei et al. (2001 ▶); Sarojini et al. (2006 ▶). For related structures, see: Betz et al. (2012 ▶); Yathirajan et al. (2007 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C16H11Cl2FO2

M = 325.15

Monoclinic,

a = 11.9035 (6) Å

b = 10.4472 (5) Å

c = 23.7435 (12) Å

β = 92.296 (4)°

V = 2950.3 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.45 mm−1

T = 173 K

0.24 × 0.20 × 0.17 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 ▶) T min = 0.900, T max = 0.927

15257 measured reflections

7015 independent reflections

5165 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.145

S = 1.06

7015 reflections

401 parameters

4 restraints

H-atom parameters constrained

Δρmax = 0.67 e Å−3

Δρmin = −0.57 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 ▶); 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 datablock(s) global, I. DOI: 10.1107/S1600536812011841/bt5846sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812011841/bt5846Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812011841/bt5846Isup3.cml

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

C16H11Cl2FO2	F(000) = 1328
Mr = 325.15	Dx = 1.464 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3879 reflections
a = 11.9035 (6) Å	θ = 3.1–30.0°
b = 10.4472 (5) Å	µ = 0.45 mm−1
c = 23.7435 (12) Å	T = 173 K
β = 92.296 (4)°	Block, colorless
V = 2950.3 (3) Å3	0.24 × 0.20 × 0.17 mm
Z = 8

Oxford Diffraction Xcalibur Eos Gemini diffractometer	7015 independent reflections
Radiation source: Enhance (Mo) X-ray Source	5165 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Detector resolution: 16.1500 pixels mm-1	θmax = 27.9°, θmin = 3.1°
ω scans	h = −10→15
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	k = −13→10
Tmin = 0.900, Tmax = 0.927	l = −30→31
15257 measured reflections

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.042P)2 + 3.2887P] where P = (Fo2 + 2Fc2)/3
7015 reflections	(Δ/σ)max < 0.001
401 parameters	Δρmax = 0.67 e Å−3
4 restraints	Δρmin = −0.57 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	Occ. (<1)
Cl1	0.73833 (6)	0.53784 (8)	0.11864 (4)	0.0566 (2)
Cl2	0.73589 (8)	0.86623 (10)	0.29381 (4)	0.0697 (3)
Cl3	0.75952 (8)	0.51754 (10)	0.41195 (6)	0.0931 (4)
Cl4	0.75948 (8)	0.21696 (11)	0.22698 (4)	0.0719 (3)
F1	0.5430 (3)	0.4344 (3)	0.16850 (18)	0.0600 (10)	0.50
F1A	0.5483 (5)	0.7210 (7)	0.3246 (2)	0.121 (2)	0.50
F2	0.9551 (3)	0.6350 (3)	0.3500 (2)	0.0771 (13)	0.50
F2A	0.9515 (4)	0.3907 (7)	0.2061 (2)	0.118 (2)	0.50
O1	0.91972 (15)	0.72821 (19)	0.18987 (9)	0.0473 (5)
O2	0.57619 (15)	1.3317 (2)	−0.00869 (9)	0.0499 (5)
O3	0.57623 (15)	0.3266 (2)	0.33521 (10)	0.0514 (5)
O4	1.00724 (16)	−0.28448 (19)	0.48786 (9)	0.0499 (5)
C1	0.6802 (2)	0.5932 (3)	0.17975 (13)	0.0418 (6)
C2	0.5874 (2)	0.5310 (3)	0.20029 (16)	0.0554 (8)
H2A	0.5557	0.4601	0.1804	0.066*	0.50
C3	0.5411 (3)	0.5714 (3)	0.24921 (17)	0.0611 (9)
H3A	0.4776	0.5287	0.2634	0.073*
C4	0.5875 (3)	0.6741 (4)	0.27727 (14)	0.0570 (9)
H4A	0.5564	0.7018	0.3114	0.068*	0.50
C5	0.6787 (2)	0.7381 (3)	0.25700 (12)	0.0451 (7)
C6	0.7264 (2)	0.6993 (2)	0.20724 (11)	0.0355 (5)
C7	0.8245 (2)	0.7701 (2)	0.18319 (11)	0.0361 (6)
C8	0.8000 (2)	0.8855 (2)	0.15059 (11)	0.0360 (5)
H8A	0.8614	0.9377	0.1405	0.043*
C9	0.6966 (2)	0.9225 (2)	0.13400 (11)	0.0357 (6)
H9A	0.6362	0.8733	0.1475	0.043*
C10	0.6665 (2)	1.0297 (2)	0.09763 (11)	0.0345 (5)
C11	0.5534 (2)	1.0535 (3)	0.08407 (13)	0.0447 (7)
H11A	0.4979	1.0002	0.0997	0.054*
C12	0.5196 (2)	1.1523 (3)	0.04865 (13)	0.0470 (7)
H12A	0.4420	1.1663	0.0400	0.056*
C13	0.5993 (2)	1.2302 (3)	0.02593 (12)	0.0376 (6)
C14	0.7130 (2)	1.2079 (3)	0.03816 (12)	0.0402 (6)
H14A	0.7680	1.2607	0.0219	0.048*
C15	0.7457 (2)	1.1101 (3)	0.07347 (12)	0.0386 (6)
H15A	0.8235	1.0964	0.0818	0.046*
C16	0.4637 (3)	1.3482 (3)	−0.02947 (16)	0.0602 (9)
H16A	0.4596	1.4221	−0.0549	0.090*
H16B	0.4148	1.3628	0.0022	0.090*
H16C	0.4390	1.2712	−0.0500	0.090*
C17	0.8124 (3)	0.4772 (3)	0.34698 (17)	0.0618 (9)
C18	0.9025 (3)	0.5439 (3)	0.3250 (3)	0.0935 (18)
H18A	0.9327	0.6150	0.3454	0.112*	0.50
C19	0.9488 (3)	0.5117 (5)	0.2757 (3)	0.104 (2)
H19A	1.0113	0.5562	0.2616	0.125*
C20	0.9013 (3)	0.4145 (4)	0.2488 (2)	0.0862 (15)
H20A	0.9319	0.3914	0.2139	0.103*	0.50
C21	0.8131 (2)	0.3439 (3)	0.26580 (15)	0.0562 (9)
C22	0.7669 (2)	0.3748 (3)	0.31718 (14)	0.0465 (7)
C23	0.6745 (2)	0.2949 (3)	0.34163 (12)	0.0406 (6)
C24	0.7103 (2)	0.1816 (3)	0.37319 (12)	0.0400 (6)
H24A	0.6546	0.1310	0.3902	0.048*
C25	0.8174 (2)	0.1453 (2)	0.37936 (11)	0.0360 (6)
H25A	0.8709	0.1979	0.3617	0.043*
C26	0.86199 (19)	0.0345 (2)	0.40993 (11)	0.0328 (5)
C27	0.9691 (2)	−0.0094 (3)	0.39798 (11)	0.0367 (6)
H27A	1.0117	0.0353	0.3713	0.044*
C28	1.0141 (2)	−0.1161 (3)	0.42405 (12)	0.0418 (6)
H28A	1.0864	−0.1458	0.4146	0.050*
C29	0.9545 (2)	−0.1804 (2)	0.46389 (11)	0.0356 (5)
C30	0.8491 (2)	−0.1371 (3)	0.47756 (12)	0.0404 (6)
H30A	0.8083	−0.1801	0.5055	0.049*
C31	0.8035 (2)	−0.0312 (3)	0.45043 (12)	0.0396 (6)
H31A	0.7307	−0.0026	0.4596	0.048*
C32	0.9572 (3)	−0.3425 (3)	0.53478 (13)	0.0508 (7)
H32A	1.0056	−0.4118	0.5494	0.076*
H32B	0.8835	−0.3773	0.5230	0.076*
H32C	0.9479	−0.2783	0.5644	0.076*

	U11	U22	U33	U12	U13	U23
Cl1	0.0398 (4)	0.0599 (5)	0.0693 (5)	0.0048 (3)	−0.0089 (3)	−0.0187 (4)
Cl2	0.0707 (6)	0.0786 (6)	0.0601 (5)	−0.0014 (5)	0.0070 (4)	−0.0206 (5)
Cl3	0.0633 (6)	0.0740 (6)	0.1389 (10)	0.0131 (5)	−0.0371 (6)	−0.0454 (7)
Cl4	0.0612 (5)	0.0891 (7)	0.0663 (6)	0.0046 (5)	0.0130 (4)	0.0001 (5)
F1	0.0344 (17)	0.0391 (17)	0.106 (3)	−0.0165 (14)	−0.0007 (17)	−0.0054 (19)
F1A	0.111 (4)	0.154 (6)	0.102 (4)	0.008 (4)	0.048 (3)	0.035 (4)
F2	0.061 (2)	0.0393 (19)	0.129 (4)	−0.0120 (18)	−0.026 (2)	−0.012 (2)
F2A	0.077 (3)	0.191 (7)	0.086 (4)	0.000 (4)	0.016 (3)	0.056 (4)
O1	0.0286 (9)	0.0475 (11)	0.0655 (13)	0.0027 (8)	−0.0018 (8)	0.0070 (10)
O2	0.0358 (10)	0.0515 (12)	0.0622 (13)	0.0030 (9)	−0.0004 (9)	0.0201 (10)
O3	0.0288 (9)	0.0486 (11)	0.0764 (15)	0.0101 (9)	−0.0027 (9)	−0.0001 (11)
O4	0.0418 (10)	0.0481 (11)	0.0606 (13)	0.0136 (9)	0.0100 (9)	0.0170 (10)
C1	0.0287 (12)	0.0377 (14)	0.0585 (18)	0.0052 (11)	−0.0052 (11)	0.0057 (13)
C2	0.0306 (14)	0.0423 (16)	0.093 (3)	−0.0017 (12)	−0.0051 (15)	0.0131 (17)
C3	0.0391 (16)	0.056 (2)	0.089 (3)	0.0004 (15)	0.0112 (16)	0.0328 (19)
C4	0.0467 (17)	0.070 (2)	0.0554 (19)	0.0143 (16)	0.0148 (14)	0.0232 (17)
C5	0.0413 (15)	0.0473 (16)	0.0468 (16)	0.0065 (13)	−0.0002 (12)	0.0086 (13)
C6	0.0270 (12)	0.0346 (13)	0.0445 (14)	0.0044 (10)	−0.0036 (10)	0.0077 (11)
C7	0.0307 (12)	0.0364 (13)	0.0410 (14)	−0.0006 (10)	−0.0006 (10)	−0.0016 (11)
C8	0.0323 (12)	0.0354 (13)	0.0402 (14)	−0.0037 (10)	0.0011 (10)	0.0012 (11)
C9	0.0312 (12)	0.0336 (13)	0.0424 (14)	−0.0019 (10)	0.0034 (10)	0.0000 (11)
C10	0.0287 (11)	0.0339 (13)	0.0409 (14)	−0.0003 (10)	0.0013 (10)	0.0003 (11)
C11	0.0280 (12)	0.0464 (15)	0.0602 (18)	−0.0030 (11)	0.0065 (12)	0.0119 (14)
C12	0.0273 (12)	0.0516 (17)	0.0621 (19)	0.0025 (12)	0.0019 (12)	0.0139 (15)
C13	0.0318 (12)	0.0367 (13)	0.0442 (15)	0.0015 (11)	−0.0005 (10)	0.0028 (12)
C14	0.0308 (12)	0.0400 (14)	0.0499 (16)	−0.0041 (11)	0.0027 (11)	0.0063 (12)
C15	0.0274 (12)	0.0395 (14)	0.0486 (15)	−0.0014 (11)	−0.0029 (10)	0.0029 (12)
C16	0.0421 (16)	0.059 (2)	0.078 (2)	0.0068 (15)	−0.0109 (15)	0.0170 (18)
C17	0.0412 (16)	0.0400 (16)	0.102 (3)	0.0077 (13)	−0.0227 (17)	0.0070 (17)
C18	0.048 (2)	0.050 (2)	0.178 (5)	−0.0162 (18)	−0.052 (3)	0.047 (3)
C19	0.041 (2)	0.103 (4)	0.166 (5)	−0.017 (2)	−0.022 (3)	0.098 (4)
C20	0.0372 (18)	0.099 (3)	0.121 (4)	−0.001 (2)	−0.007 (2)	0.073 (3)
C21	0.0315 (14)	0.0593 (19)	0.078 (2)	0.0049 (13)	−0.0020 (14)	0.0289 (18)
C22	0.0287 (13)	0.0353 (14)	0.075 (2)	0.0052 (11)	−0.0088 (13)	0.0157 (14)
C23	0.0303 (13)	0.0363 (14)	0.0549 (17)	0.0047 (11)	−0.0011 (11)	−0.0043 (13)
C24	0.0309 (12)	0.0375 (13)	0.0518 (16)	0.0017 (11)	0.0052 (11)	0.0027 (12)
C25	0.0317 (12)	0.0324 (12)	0.0440 (15)	0.0010 (10)	0.0020 (10)	−0.0013 (11)
C26	0.0286 (11)	0.0312 (12)	0.0384 (14)	0.0008 (10)	−0.0013 (10)	−0.0047 (11)
C27	0.0290 (12)	0.0388 (13)	0.0425 (14)	0.0020 (10)	0.0054 (10)	0.0031 (12)
C28	0.0287 (12)	0.0472 (15)	0.0498 (16)	0.0081 (11)	0.0069 (11)	0.0037 (13)
C29	0.0326 (12)	0.0328 (12)	0.0412 (14)	0.0046 (10)	−0.0009 (10)	0.0014 (11)
C30	0.0361 (13)	0.0418 (14)	0.0439 (15)	0.0021 (12)	0.0094 (11)	0.0047 (12)
C31	0.0298 (12)	0.0402 (14)	0.0496 (16)	0.0057 (11)	0.0096 (11)	0.0015 (12)
C32	0.0507 (17)	0.0482 (17)	0.0536 (18)	0.0037 (14)	0.0040 (14)	0.0162 (14)

Cl1—C1	1.732 (3)	C14—H14A	0.9500
Cl2—C5	1.724 (3)	C15—H15A	0.9500
Cl3—C17	1.741 (4)	C16—H16A	0.9800
Cl4—C21	1.723 (4)	C16—H16B	0.9800
O1—C7	1.220 (3)	C16—H16C	0.9800
O2—C13	1.363 (3)	C17—C22	1.381 (4)
O2—C16	1.419 (3)	C17—C18	1.398 (6)
O3—C23	1.219 (3)	C18—C19	1.354 (7)
O4—C29	1.369 (3)	C18—H18A	0.9500
O4—C32	1.420 (3)	C19—C20	1.315 (7)
C1—C2	1.387 (4)	C19—H19A	0.9500
C1—C6	1.388 (4)	C20—C21	1.359 (5)
C2—C3	1.372 (5)	C20—H20A	0.9500
C2—H2A	0.9500	C21—C22	1.396 (5)
C3—C4	1.368 (5)	C22—C23	1.516 (4)
C3—H3A	0.9500	C23—C24	1.456 (4)
C4—C5	1.378 (4)	C24—C25	1.333 (3)
C4—H4A	0.9500	C24—H24A	0.9500
C5—C6	1.391 (4)	C25—C26	1.455 (3)
C6—C7	1.514 (3)	C25—H25A	0.9500
C7—C8	1.456 (4)	C26—C31	1.391 (4)
C8—C9	1.335 (3)	C26—C27	1.395 (3)
C8—H8A	0.9500	C27—C28	1.373 (4)
C9—C10	1.450 (4)	C27—H27A	0.9500
C9—H9A	0.9500	C28—C29	1.379 (4)
C10—C11	1.393 (3)	C28—H28A	0.9500
C10—C15	1.403 (3)	C29—C30	1.384 (3)
C11—C12	1.381 (4)	C30—C31	1.381 (4)
C11—H11A	0.9500	C30—H30A	0.9500
C12—C13	1.376 (4)	C31—H31A	0.9500
C12—H12A	0.9500	C32—H32A	0.9800
C13—C14	1.393 (3)	C32—H32B	0.9800
C14—C15	1.368 (4)	C32—H32C	0.9800
C13—O2—C16	118.0 (2)	H16B—C16—H16C	109.5
C29—O4—C32	117.7 (2)	C22—C17—C18	119.0 (4)
C2—C1—C6	120.9 (3)	C22—C17—Cl3	119.5 (3)
C2—C1—Cl1	119.3 (2)	C18—C17—Cl3	121.4 (3)
C6—C1—Cl1	119.8 (2)	C19—C18—C17	122.9 (4)
C3—C2—C1	120.5 (3)	C19—C18—H18A	118.5
C3—C2—H2A	119.8	C17—C18—H18A	118.5
C1—C2—H2A	119.8	C20—C19—C18	115.5 (4)
C4—C3—C2	119.0 (3)	C20—C19—H19A	122.3
C4—C3—H3A	120.5	C18—C19—H19A	122.3
C2—C3—H3A	120.5	C19—C20—C21	126.7 (5)
C3—C4—C5	121.3 (3)	C19—C20—H20A	116.7
C3—C4—H4A	119.3	C21—C20—H20A	116.7
C5—C4—H4A	119.3	C20—C21—C22	118.0 (4)
C4—C5—C6	120.6 (3)	C20—C21—Cl4	122.2 (3)
C4—C5—Cl2	120.0 (3)	C22—C21—Cl4	119.7 (2)
C6—C5—Cl2	119.4 (2)	C17—C22—C21	117.9 (3)
C1—C6—C5	117.7 (2)	C17—C22—C23	120.4 (3)
C1—C6—C7	120.6 (2)	C21—C22—C23	121.6 (3)
C5—C6—C7	121.7 (2)	O3—C23—C24	123.1 (3)
O1—C7—C8	122.1 (2)	O3—C23—C22	120.6 (2)
O1—C7—C6	120.2 (2)	C24—C23—C22	116.3 (2)
C8—C7—C6	117.7 (2)	C25—C24—C23	123.2 (3)
C9—C8—C7	124.0 (2)	C25—C24—H24A	118.4
C9—C8—H8A	118.0	C23—C24—H24A	118.4
C7—C8—H8A	118.0	C24—C25—C26	127.5 (2)
C8—C9—C10	127.0 (2)	C24—C25—H25A	116.2
C8—C9—H9A	116.5	C26—C25—H25A	116.2
C10—C9—H9A	116.5	C31—C26—C27	117.7 (2)
C11—C10—C15	117.2 (2)	C31—C26—C25	123.7 (2)
C11—C10—C9	119.3 (2)	C27—C26—C25	118.6 (2)
C15—C10—C9	123.5 (2)	C28—C27—C26	121.2 (2)
C12—C11—C10	122.0 (2)	C28—C27—H27A	119.4
C12—C11—H11A	119.0	C26—C27—H27A	119.4
C10—C11—H11A	119.0	C27—C28—C29	120.1 (2)
C13—C12—C11	119.5 (2)	C27—C28—H28A	119.9
C13—C12—H12A	120.3	C29—C28—H28A	119.9
C11—C12—H12A	120.3	O4—C29—C28	115.6 (2)
O2—C13—C12	124.8 (2)	O4—C29—C30	124.6 (2)
O2—C13—C14	115.3 (2)	C28—C29—C30	119.9 (2)
C12—C13—C14	119.9 (2)	C31—C30—C29	119.7 (2)
C15—C14—C13	120.2 (2)	C31—C30—H30A	120.2
C15—C14—H14A	119.9	C29—C30—H30A	120.2
C13—C14—H14A	119.9	C30—C31—C26	121.3 (2)
C14—C15—C10	121.2 (2)	C30—C31—H31A	119.3
C14—C15—H15A	119.4	C26—C31—H31A	119.3
C10—C15—H15A	119.4	O4—C32—H32A	109.5
O2—C16—H16A	109.5	O4—C32—H32B	109.5
O2—C16—H16B	109.5	H32A—C32—H32B	109.5
H16A—C16—H16B	109.5	O4—C32—H32C	109.5
O2—C16—H16C	109.5	H32A—C32—H32C	109.5
H16A—C16—H16C	109.5	H32B—C32—H32C	109.5
C6—C1—C2—C3	−1.8 (4)	C22—C17—C18—C19	−0.9 (5)
Cl1—C1—C2—C3	178.8 (2)	Cl3—C17—C18—C19	177.1 (3)
C1—C2—C3—C4	0.2 (5)	C17—C18—C19—C20	1.7 (6)
C2—C3—C4—C5	0.8 (5)	C18—C19—C20—C21	−1.0 (6)
C3—C4—C5—C6	−0.3 (4)	C19—C20—C21—C22	−0.5 (5)
C3—C4—C5—Cl2	−179.4 (2)	C19—C20—C21—Cl4	−179.1 (3)
C2—C1—C6—C5	2.2 (4)	C18—C17—C22—C21	−0.7 (4)
Cl1—C1—C6—C5	−178.3 (2)	Cl3—C17—C22—C21	−178.7 (2)
C2—C1—C6—C7	−177.3 (2)	C18—C17—C22—C23	175.9 (3)
Cl1—C1—C6—C7	2.2 (3)	Cl3—C17—C22—C23	−2.2 (4)
C4—C5—C6—C1	−1.2 (4)	C20—C21—C22—C17	1.3 (4)
Cl2—C5—C6—C1	177.96 (19)	Cl4—C21—C22—C17	180.0 (2)
C4—C5—C6—C7	178.3 (3)	C20—C21—C22—C23	−175.1 (3)
Cl2—C5—C6—C7	−2.5 (3)	Cl4—C21—C22—C23	3.5 (4)
C1—C6—C7—O1	−79.7 (3)	C17—C22—C23—O3	86.1 (4)
C5—C6—C7—O1	100.9 (3)	C21—C22—C23—O3	−97.5 (3)
C1—C6—C7—C8	98.1 (3)	C17—C22—C23—C24	−93.0 (3)
C5—C6—C7—C8	−81.3 (3)	C21—C22—C23—C24	83.4 (3)
O1—C7—C8—C9	167.9 (3)	O3—C23—C24—C25	178.7 (3)
C6—C7—C8—C9	−9.8 (4)	C22—C23—C24—C25	−2.2 (4)
C7—C8—C9—C10	−174.4 (2)	C23—C24—C25—C26	179.9 (3)
C8—C9—C10—C11	179.2 (3)	C24—C25—C26—C31	−18.7 (4)
C8—C9—C10—C15	1.2 (4)	C24—C25—C26—C27	160.9 (3)
C15—C10—C11—C12	−0.4 (4)	C31—C26—C27—C28	1.8 (4)
C9—C10—C11—C12	−178.5 (3)	C25—C26—C27—C28	−177.7 (2)
C10—C11—C12—C13	−0.1 (5)	C26—C27—C28—C29	−1.6 (4)
C16—O2—C13—C12	−9.4 (4)	C32—O4—C29—C28	170.9 (3)
C16—O2—C13—C14	170.9 (3)	C32—O4—C29—C30	−8.3 (4)
C11—C12—C13—O2	−178.8 (3)	C27—C28—C29—O4	−179.2 (2)
C11—C12—C13—C14	0.9 (5)	C27—C28—C29—C30	0.0 (4)
O2—C13—C14—C15	178.6 (3)	O4—C29—C30—C31	−179.7 (3)
C12—C13—C14—C15	−1.1 (4)	C28—C29—C30—C31	1.2 (4)
C13—C14—C15—C10	0.6 (4)	C29—C30—C31—C26	−0.8 (4)
C11—C10—C15—C14	0.1 (4)	C27—C26—C31—C30	−0.6 (4)
C9—C10—C15—C14	178.2 (3)	C25—C26—C31—C30	178.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···F1Ai	0.95	2.79	3.657 (7)	153
C4—H4A···F1ii	0.95	2.75	3.410 (5)	127
C11—H11A···O3ii	0.95	2.56	3.451 (3)	156

CgI···CgJ	Cg···Cg (Å)	CgI Perp (Å)	Cgj Perp (Å)
Cg1···Cg3i	3.650 (2)	3.620	3.604

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯F1Ai	0.95	2.79	3.657 (7)	153
C4—H4A⋯F1ii	0.95	2.75	3.410 (5)	127
C11—H11A⋯O3ii	0.95	2.56	3.451 (3)	156

Symmetry codes: (i) ; (ii) .