Crystal structure and Hirshfeld surface analysis of (2E)-3-(4-chloro-3-fluoro-phen-yl)-1-(3,4-di-meth-oxy-phen-yl)prop-2-en-1-one.

The mol-ecular structure of the title compound, C17H14ClFO3, consists of a 4-chloro-3-fluoro-phenyl ring and a 3,4-di-meth-oxy-phenyl ring linked via a prop-2-en-1-one spacer. The mol-ecule has an E configuration about the C=C bond and the carbonyl group is syn with respect to the C=C bond. The F and H atoms at the meta positions of the 4-chloro-3-fluoro-phenyl ring are disordered over two orientations, with an occupancy ratio of 0.785 (3):0.215 (3). In the crystal, mol-ecules are linked via pairs of C-H⋯O inter-actions with an R 2 2(14) ring motif, forming inversion dimers. The dimers are linked into a tape structure running along [10] by a C-H⋯π inter-action. The inter-molecular contacts in the crystal were further analysed using Hirshfield surface analysis, which indicates that the most significant contacts are H⋯H (25.0%), followed by C⋯H/H⋯C (20.6%), O⋯H/H⋯O (15.6%), Cl⋯H/H⋯Cl (10.7%), F⋯H/H⋯F (10.4%), F⋯C/C⋯F (7.2%) and C⋯C (3.0%).

Chemical context

Chalcones, compounds with a 1,3-di­phenyl­prop-2-en-1-one framework, are considered to be the precursors of flavonoids and isoflavonoids, which are abundant in edible plants. These compounds are coloured via the –CO—CH=CH– chromophore and other auxochromes. Chalcones attract significant attention because of their availability of high optical non-linearities arising from the delocalization of π-conjugated electron clouds throughout the chalcone system, which provides a large charge-transfer axis with appropriate substituents on the terminal aromatic rings. π-conjugated systems have been studied extensively for their optoelectronic properties (Shetty et al., 2016 ▸, 2017 ▸) because of the possibility of developing low-cost, large-area and flexible electronic devices. In view of all the above and in a continuation of our previous work on 3,4-dimeth­oxy chalcones (Sheshadri et al., 2018a ▸,b ▸), we report herein the crystal and mol­ecular structure of the title compound.

Structural commentary

The title compound (Fig. 1 ▸) is composed of two aromatic rings, 4-chloro-3-fluoro­phenyl and 3,4-di­meth­oxy­phenyl, which are linked by a –CO—CH=CH– enone bridge. The mol­ecule is approximately planar as indicated by the torsion angles C1—C6—C7—O3 = 174.71 (16)°, C1—C6—C7—C8 = −3.8 (2)°, C6—C7—C8—C9 = 178.49 (15)°, O3—C7—C8—C9 = 0.0 (3)°, C8—C9—C10—C11 = 178.22 (17)° and C7—C8—C9—C10 = −179.00 (15)°. The dihedral angle between the 4-chloro-3-fluoro­phenyl and 3,4-di­meth­oxy­phenyl rings is 5.40 (7)°. The H atoms of the central propenone group are trans configured. The two meth­oxy groups attached to atoms C3 and C4 are almost coplanar with the benzene ring, with deviations of 0.214 (2) Å for C16 and 0.209 (2) Å for C17. The 4-chloro-3-fluoro­phenyl fragment is disordered over two orientations around the C9—C10 bond axis, with an occupancy ratio of 0.785 (3):0.215 (3).

Figure 1

The mol­ecular structure of the title compound, showing the atom labelling and displacement ellipsoids drawn at the 50% probability level.

Supra­molecular features and Hirshfeld surface analysis

In the crystal, the mol­ecules are connected into inversion dimers with an (14) ring motif (Fig. 2 ▸) via pairs of C—H⋯O inter­actions (Table 1 ▸). The dimers are further linked by a C—H⋯π inter­action (Table 1 ▸), forming a tape structure along [10] (Fig. 3 ▸).

Figure 2

A packing diagram of the title compound viewed along the a axis, showing mol­ecular dimers formed by the inter­molecular C—H⋯O hydrogen bonds (dashed lines). The minor disorder component and H atoms not involved in the hydrogen bonds are omitted for clarity.

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O3i	0.93	2.57	3.426 (2)	152
C2—H2⋯Cg1ii	0.93	2.81	3.5832 (16)	142

Symmetry codes: (i) ; (ii) .

Figure 3

A packing diagram of the title compound viewed along the a axis, showing inter­molecular C—H⋯O and C—H⋯π inter­actions (dashed lines). The minor disorder component and H atoms not involved in the hydrogen bonds are omitted for clarity.

The Hirshfeld surface and two-dimensional fingerprint plots of the title compound were calculated using CrystalExplorer17.5 (Turner et al., 2017 ▸). In the Hirshfeld surface plotted over d norm (Fig. 4 ▸), the white surfaces indicate contacts with distances equal to the sum of van der Waals radii, and the red and blue colours indicate distances shorter or longer than the van der Waals radii, respectively (Venkatesan et al., 2016 ▸). The overall two-dimensional fingerprint plot and those delineated into H⋯H (25.0%), C⋯H/H⋯C (20.6%), O⋯H/H⋯O (15.6%), Cl⋯H/H⋯Cl (10.7%), F⋯H/H⋯F (10.4%), F⋯C/C⋯F (7.2%) and C⋯C (3.0%) contacts (McKinnon et al., 2007 ▸) are illustrated in Fig. 5 ▸ a–h, respectively. The small percentage contributions from the other different inter­atomic contacts to the Hirshfeld surfaces are as follows: Cl⋯O/O⋯Cl (2.7%), O⋯C/C⋯O (1.7%), Cl⋯C/C⋯Cl (1.1%), F⋯F (0.9%), Cl⋯F/F⋯Cl (0.7%) and F⋯O/O⋯F (0.2%).

Figure 4

Plot of d norm mapped on the Hirshfeld surfaces of the title compound showing the short H⋯O contacts.

Figure 5

Hirshfeld surface representations and the overall two-dimensional fingerprint plots of the title compound, showing (a) all inter­actions, and delineated into (b) H⋯H, (c) C⋯H/H⋯C, (d) O⋯H/H⋯O, (e) Cl⋯H/H⋯Cl, (f) F⋯H/H⋯F, (g) F⋯C/C⋯F and (h) C⋯C inter­actions [d e and d i represent the distances from a point on the Hirshfeld surface to the nearest atoms outside (external) and inside (inter­nal) the surface, respectively].

Database survey

A search of the Cambridge Structural Database (CSD, version 5.40, update of February 2019; Groom et al., 2016 ▸) using (E)-1,3-di­phenyl­prop-2-en-1-one as the main skeleton revealed 3314 hits. Six structures containing the (E)-1,3-di­phenyl­prop-2-en-1-one framework with different substituents that are similar to the title compound were found, viz. 3-(3-chloro­phen­yl)-1-(3,4-di­meth­oxy­phen­yl)prop-2-en-1-one (VIDVEM; Sheshadri et al., 2018a ▸), 3-(3-bromo-4-fluoro­phen­yl)-1-(3,4-di­meth­oxy­phen­yl)prop-2-en-1-one (BIBWOB; Sheshadri et al., 2018b ▸), (E)-3-(2-bromo­phen­yl)-1-(3,4-di­meth­oxy­phen­yl)prop-2-en-1-one (LAPREB; Li et al., 2012 ▸), (E)-1-(3,5-di­fluoro­phen­yl)-3-(2,4-di­meth­oxy­phen­yl)prop-2-en-1-one (KUZFOB; Huang et al., 2010 ▸), (E)-1-(3-bromo­phen­yl)-3-(3,4-di­meth­oxy­phen­yl)prop-2-en-1-one (LAQWUX; Escobar et al., 2012 ▸) and 3-(3,4-di­meth­oxy­phen­yl)-1-(4-fluoro­phen­yl)-prop-2-en-1-one(MEGQOF; Butcher et al., 2006 ▸).

For these similar compounds, the dihedral angles between the two terminal benzene rings, which are linked by a –CO—CH=CH– enone bridge are 18.46 (7)° for VIDVEM, 17.91 (17)° for BIBWOB, 9.3 (2) and 19.4 (2)° (two crystallographically independent mol­ecules) for LAPREB, 5.46 (2)° for KUZFOB, 26.59 (9)° for LAQWUX and 47.81 (6) and 50.18 (5)° (two crystallographically independent mol­ecules) for MEGQOF. In the crystals of VIDVEM and BIBWOB, mol­ecules are linked by C—H⋯O hydrogen bonds, forming dimers with (14) ring motifs, and the dimers are further linked by other C—H⋯O hydrogen contacts, forming two-dimensional supra­molecular structures. In the crystal of LAPREB, mol­ecules are also linked through weak inter­molecular C—H⋯O hydrogen bonds. The crystal structure of KUZFOB is stabilized by inter­molecular C—H⋯F hydrogen bonds.

Synthesis and crystallization

The title compound was synthesized as per the procedure reported earlier (Kumar et al., 2013a ▸,b ▸). 1-(3,4-Di­meth­oxy­phen­yl)ethanone (0.01 mol) and 4-chloro-3-fluoro­benzaldehyde (0.01 mol) were dissolved in 20 ml of methanol. A catalytic amount of NaOH was added to the solution dropwise with vigorous stirring. The reaction mixture was stirred for about 3 h at room temperature. The formed crude products were filtered, washed successively with distilled water and recrystallized from methanol to get the title compound (m.p. 384–388 K).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2 ▸. The C-bound H atoms were positioned geometrically (C—H = 0.93 or 0.96 Å) and refined using a riding model, with U iso(H) = 1.2 or 1.5U eq(C). The 4-chloro-3-fluoro­phenyl fragment was found to be disordered in a difference-Fourier map, and the F and H atoms at the meta positions of the benzene ring were treated as disordered over two sites with an occupancy ratio of 0.785 (3):0.215 (3).

Table 2

Experimental details

Crystal data
Chemical formula	C17H14ClFO3
M r	320.73
Crystal system, space group	Monoclinic, P21/n
Temperature (K)	294
a, b, c (Å)	14.9088 (13), 5.7669 (5), 17.9074 (15)
β (°)	104.491 (2)
V (Å3)	1490.7 (2)
Z	4
Radiation type	Mo Kα
μ (mm−1)	0.28
Crystal size (mm)	0.45 × 0.37 × 0.30
Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 2007 ▸)
T min, T max	0.884, 0.921
No. of measured, independent and observed [I > 2σ(I)] reflections	16268, 4334, 3195
R int	0.024
(sin θ/λ)max (Å−1)	0.704
Refinement
R[F 2 > 2σ(F 2)], wR(F 2), S	0.047, 0.143, 1.05
No. of reflections	4334
No. of parameters	211
H-atom treatment	H-atom parameters constrained
Δρmax, Δρmin (e Å−3)	0.33, −0.36

Computer programs: APEX2 and SAINT (Bruker, 2007 ▸), SHELXS97 (Sheldrick, 2008 ▸), SHELXL2014 (Sheldrick, 2015 ▸), ORTEP-3 for Windows (Farrugia, 2012 ▸) and PLATON (Spek, 2009 ▸).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989019007783/is5515sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989019007783/is5515Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989019007783/is5515Isup3.cml

CCDC reference: 1919577

Additional supporting information: crystallographic information; 3D view; checkCIF report

C17H14ClFO3	F(000) = 664
Mr = 320.73	Dx = 1.429 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 14.9088 (13) Å	Cell parameters from 5099 reflections
b = 5.7669 (5) Å	θ = 2.4–29.4°
c = 17.9074 (15) Å	µ = 0.28 mm−1
β = 104.491 (2)°	T = 294 K
V = 1490.7 (2) Å3	Block, colourless
Z = 4	0.45 × 0.37 × 0.30 mm

Bruker APEXII CCD diffractometer	3195 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.024
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	θmax = 30.0°, θmin = 1.6°
Tmin = 0.884, Tmax = 0.921	h = −19→20
16268 measured reflections	k = −8→7
4334 independent reflections	l = −25→25

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047	H-atom parameters constrained
wR(F2) = 0.143	w = 1/[σ2(Fo2) + (0.0736P)2 + 0.2421P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
4334 reflections	Δρmax = 0.33 e Å−3
211 parameters	Δρmin = −0.36 e Å−3

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1	0.36793 (3)	0.45137 (9)	0.15399 (3)	0.06876 (17)
F1	0.34304 (9)	0.0254 (3)	0.06801 (10)	0.0765 (6)	0.785 (3)
F1A	0.1946 (4)	0.5065 (11)	0.2007 (4)	0.094 (2)	0.215 (3)
O1	−0.44876 (7)	−0.2364 (2)	0.18315 (7)	0.0525 (3)
O2	−0.42868 (8)	−0.5737 (2)	0.09682 (7)	0.0534 (3)
O3	−0.11186 (9)	−0.4829 (2)	0.04648 (8)	0.0690 (4)
C1	−0.21547 (10)	−0.0994 (3)	0.16131 (8)	0.0438 (3)
H1	−0.168526	0.009416	0.177135	0.053*
C2	−0.29625 (10)	−0.0816 (3)	0.18676 (8)	0.0439 (3)
H2	−0.302640	0.038463	0.219715	0.053*
C3	−0.36666 (9)	−0.2405 (2)	0.16343 (8)	0.0388 (3)
C4	−0.35591 (9)	−0.4244 (2)	0.11467 (7)	0.0392 (3)
C5	−0.27631 (10)	−0.4408 (2)	0.08964 (8)	0.0412 (3)
H5	−0.269807	−0.561469	0.056957	0.049*
C6	−0.20461 (9)	−0.2784 (2)	0.11254 (8)	0.0400 (3)
C7	−0.11934 (10)	−0.3123 (3)	0.08476 (9)	0.0462 (3)
C8	−0.04346 (11)	−0.1412 (3)	0.10561 (9)	0.0514 (4)
H8	−0.050846	−0.012603	0.134851	0.062*
C9	0.03440 (10)	−0.1648 (3)	0.08409 (9)	0.0468 (3)
H9	0.038821	−0.294198	0.054228	0.056*
C10	0.11470 (10)	−0.0096 (3)	0.10207 (8)	0.0437 (3)
C11	0.19219 (11)	−0.0652 (3)	0.07626 (9)	0.0495 (4)
H11	0.192714	−0.199152	0.047458	0.059*
C12	0.26843 (10)	0.0782 (3)	0.09329 (9)	0.0503 (4)
H12A	0.319949	0.038662	0.075551	0.060*	0.215 (3)
C13	0.27083 (10)	0.2763 (3)	0.13536 (9)	0.0484 (3)
C14	0.19390 (13)	0.3344 (3)	0.16078 (11)	0.0613 (4)
H14	0.194093	0.469027	0.189426	0.074*	0.785 (3)
C15	0.11650 (12)	0.1938 (3)	0.14396 (11)	0.0597 (4)
H15	0.064721	0.235966	0.160943	0.072*
C16	−0.46843 (13)	−0.0410 (3)	0.22426 (11)	0.0599 (4)
H16A	−0.531649	−0.047899	0.227596	0.090*
H16B	−0.458981	0.098166	0.197789	0.090*
H16C	−0.428007	−0.040654	0.275248	0.090*
C17	−0.43044 (13)	−0.7381 (3)	0.03698 (10)	0.0576 (4)
H17A	−0.487558	−0.823211	0.026665	0.086*
H17B	−0.379347	−0.843355	0.052900	0.086*
H17C	−0.425610	−0.658282	−0.008901	0.086*

	U11	U22	U33	U12	U13	U23
Cl1	0.0483 (3)	0.0636 (3)	0.0962 (4)	−0.01829 (19)	0.0215 (2)	−0.0083 (2)
F1	0.0457 (8)	0.0828 (11)	0.1146 (12)	−0.0100 (6)	0.0454 (8)	−0.0308 (8)
F1A	0.075 (4)	0.081 (4)	0.137 (5)	−0.023 (3)	0.048 (4)	−0.061 (4)
O1	0.0380 (5)	0.0559 (7)	0.0690 (7)	−0.0088 (5)	0.0234 (5)	−0.0118 (5)
O2	0.0445 (6)	0.0533 (7)	0.0650 (6)	−0.0199 (5)	0.0186 (5)	−0.0151 (5)
O3	0.0533 (7)	0.0692 (8)	0.0944 (9)	−0.0154 (6)	0.0372 (7)	−0.0334 (7)
C1	0.0334 (7)	0.0433 (7)	0.0550 (8)	−0.0086 (5)	0.0120 (6)	−0.0064 (6)
C2	0.0380 (7)	0.0425 (7)	0.0519 (7)	−0.0042 (6)	0.0128 (6)	−0.0098 (6)
C3	0.0314 (6)	0.0423 (7)	0.0430 (6)	−0.0021 (5)	0.0101 (5)	0.0017 (5)
C4	0.0337 (6)	0.0398 (7)	0.0429 (6)	−0.0075 (5)	0.0075 (5)	−0.0002 (5)
C5	0.0388 (7)	0.0416 (7)	0.0441 (7)	−0.0053 (5)	0.0120 (6)	−0.0054 (5)
C6	0.0333 (6)	0.0432 (7)	0.0442 (6)	−0.0045 (5)	0.0111 (5)	−0.0013 (5)
C7	0.0371 (7)	0.0517 (8)	0.0523 (7)	−0.0063 (6)	0.0158 (6)	−0.0053 (6)
C8	0.0404 (7)	0.0550 (9)	0.0635 (9)	−0.0096 (7)	0.0215 (7)	−0.0107 (7)
C9	0.0376 (7)	0.0530 (9)	0.0522 (7)	−0.0065 (6)	0.0159 (6)	−0.0045 (6)
C10	0.0359 (7)	0.0507 (8)	0.0471 (7)	−0.0039 (6)	0.0153 (6)	−0.0011 (6)
C11	0.0406 (8)	0.0534 (9)	0.0586 (8)	−0.0035 (6)	0.0197 (6)	−0.0116 (7)
C12	0.0349 (7)	0.0591 (9)	0.0614 (8)	−0.0020 (6)	0.0206 (6)	−0.0032 (7)
C13	0.0387 (7)	0.0510 (8)	0.0569 (8)	−0.0088 (6)	0.0147 (6)	−0.0008 (6)
C14	0.0558 (10)	0.0581 (10)	0.0773 (11)	−0.0098 (8)	0.0305 (9)	−0.0195 (9)
C15	0.0465 (9)	0.0625 (10)	0.0807 (11)	−0.0084 (7)	0.0360 (8)	−0.0177 (8)
C16	0.0514 (9)	0.0636 (11)	0.0738 (11)	−0.0024 (8)	0.0328 (8)	−0.0113 (8)
C17	0.0550 (9)	0.0507 (9)	0.0636 (9)	−0.0141 (7)	0.0082 (7)	−0.0145 (7)

Cl1—C13	1.7278 (15)	C8—H8	0.9300
F1—C12	1.3367 (18)	C9—C10	1.465 (2)
F1A—C14	1.222 (5)	C9—H9	0.9300
O1—C3	1.3565 (16)	C10—C11	1.3851 (19)
O1—C16	1.416 (2)	C10—C15	1.389 (2)
O2—C4	1.3590 (16)	C11—C12	1.376 (2)
O2—C17	1.4259 (19)	C11—H11	0.9300
O3—C7	1.2202 (19)	C12—C13	1.364 (2)
C1—C6	1.3876 (19)	C12—H12A	0.9300
C1—C2	1.3940 (19)	C13—C14	1.377 (2)
C1—H1	0.9300	C14—C15	1.381 (2)
C2—C3	1.3772 (19)	C14—H14	0.9300
C2—H2	0.9300	C15—H15	0.9300
C3—C4	1.4082 (19)	C16—H16A	0.9600
C4—C5	1.3727 (19)	C16—H16B	0.9600
C5—C6	1.4028 (19)	C16—H16C	0.9600
C5—H5	0.9300	C17—H17A	0.9600
C6—C7	1.4893 (19)	C17—H17B	0.9600
C7—C8	1.477 (2)	C17—H17C	0.9600
C8—C9	1.319 (2)
C3—O1—C16	117.83 (12)	C12—C11—C10	119.90 (14)
C4—O2—C17	117.47 (12)	C12—C11—H11	120.1
C6—C1—C2	120.47 (13)	C10—C11—H11	120.1
C6—C1—H1	119.8	F1—C12—C13	117.94 (14)
C2—C1—H1	119.8	F1—C12—C11	119.95 (15)
C3—C2—C1	120.46 (13)	C13—C12—C11	122.11 (14)
C3—C2—H2	119.8	C13—C12—H12A	118.9
C1—C2—H2	119.8	C11—C12—H12A	118.9
O1—C3—C2	125.34 (13)	C12—C13—C14	118.53 (14)
O1—C3—C4	115.13 (12)	C12—C13—Cl1	120.07 (12)
C2—C3—C4	119.53 (12)	C14—C13—Cl1	121.38 (13)
O2—C4—C5	125.75 (13)	F1A—C14—C13	120.4 (3)
O2—C4—C3	114.52 (12)	F1A—C14—C15	119.3 (3)
C5—C4—C3	119.73 (12)	C13—C14—C15	120.31 (16)
C4—C5—C6	121.10 (13)	C13—C14—H14	119.8
C4—C5—H5	119.5	C15—C14—H14	119.8
C6—C5—H5	119.5	C14—C15—C10	121.06 (14)
C1—C6—C5	118.69 (12)	C14—C15—H15	119.5
C1—C6—C7	123.47 (12)	C10—C15—H15	119.5
C5—C6—C7	117.82 (12)	O1—C16—H16A	109.5
O3—C7—C8	120.58 (13)	O1—C16—H16B	109.5
O3—C7—C6	119.93 (13)	H16A—C16—H16B	109.5
C8—C7—C6	119.47 (13)	O1—C16—H16C	109.5
C9—C8—C7	122.13 (15)	H16A—C16—H16C	109.5
C9—C8—H8	118.9	H16B—C16—H16C	109.5
C7—C8—H8	118.9	O2—C17—H17A	109.5
C8—C9—C10	127.13 (15)	O2—C17—H17B	109.5
C8—C9—H9	116.4	H17A—C17—H17B	109.5
C10—C9—H9	116.4	O2—C17—H17C	109.5
C11—C10—C15	118.09 (14)	H17A—C17—H17C	109.5
C11—C10—C9	119.29 (14)	H17B—C17—H17C	109.5
C15—C10—C9	122.62 (13)
C6—C1—C2—C3	−0.4 (2)	O3—C7—C8—C9	0.0 (3)
C16—O1—C3—C2	7.1 (2)	C6—C7—C8—C9	178.49 (15)
C16—O1—C3—C4	−172.50 (14)	C7—C8—C9—C10	−179.00 (15)
C1—C2—C3—O1	−178.37 (14)	C8—C9—C10—C11	178.22 (17)
C1—C2—C3—C4	1.2 (2)	C8—C9—C10—C15	−2.1 (3)
C17—O2—C4—C5	−11.5 (2)	C15—C10—C11—C12	0.9 (3)
C17—O2—C4—C3	168.72 (13)	C9—C10—C11—C12	−179.46 (15)
O1—C3—C4—O2	−1.91 (18)	C10—C11—C12—F1	−179.59 (16)
C2—C3—C4—O2	178.50 (13)	C10—C11—C12—C13	0.0 (3)
O1—C3—C4—C5	178.26 (13)	F1—C12—C13—C14	179.06 (17)
C2—C3—C4—C5	−1.3 (2)	C11—C12—C13—C14	−0.6 (3)
O2—C4—C5—C6	−179.07 (13)	F1—C12—C13—Cl1	0.4 (2)
C3—C4—C5—C6	0.7 (2)	C11—C12—C13—Cl1	−179.23 (14)
C2—C1—C6—C5	−0.2 (2)	C12—C13—C14—F1A	177.6 (5)
C2—C1—C6—C7	−178.27 (14)	Cl1—C13—C14—F1A	−3.8 (5)
C4—C5—C6—C1	0.0 (2)	C12—C13—C14—C15	0.2 (3)
C4—C5—C6—C7	178.21 (13)	Cl1—C13—C14—C15	178.81 (15)
C1—C6—C7—O3	174.71 (16)	F1A—C14—C15—C10	−176.7 (5)
C5—C6—C7—O3	−3.4 (2)	C13—C14—C15—C10	0.8 (3)
C1—C6—C7—C8	−3.8 (2)	C11—C10—C15—C14	−1.3 (3)
C5—C6—C7—C8	178.12 (14)	C9—C10—C15—C14	179.08 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O3i	0.93	2.57	3.426 (2)	152
C2—H2···Cg1ii	0.93	2.81	3.5832 (16)	142