(1RS,6SR)-Ethyl 4-(4-chloro-phen-yl)-6-(4-fluoro-phen-yl)-2-oxocyclo-hex-3-ene-1-carboxyl-ate toluene hemisolvate.

In the crystal structure of the title compound, C(21)H(18)ClFO(3)·0.5C(7)H(8), the toluene solvent mol-ecules occupy special positions on centres of symmetry, and consequently are disordered across this site. The cyclo-hexene ring has a slightly distorted sofa conformation; the two benzene rings are inclined by 72.90 (7)° and their planes make dihedral angles of 30.09 (10) (chloro-phen-yl) and 88.13 (6)° (fluoro-phen-yl) with the approximately planar part of the cyclo-hexenone ring [maximum deviation from plane through five atoms is 0.030 (2) Å, the sixth atom is 0.672 (3)Å out of this plane]. Weak inter-molecular C-H⋯O and C-H⋯X (X = F, Cl) inter-actions join mol-ecules into a three-dimensional structure. Also, a relatively short and directional C-Cl⋯F-C contact is observed [Cl⋯F = 3.119 (2) Å, C-Cl⋯F = 157.5 (2)° and C-F⋯Cl 108.3 (2)°]. The solvent mol-ecules fill the voids in the crystal structure and are kept there by relatively short and directional C-H⋯π inter-actions.

Related literature

For biological applications of some cyclo­hexa­nones, see: Eddington et al. (2000 ▶). For asymmetry parameters, see: Duax & Norton (1975 ▶). For similar structures, see: in Anuradha et al. (2009 ▶); Fun et al. (2008 ▶, 2009 ▶, 2010 ▶); Badshah et al. (2009 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C21H18ClFO3·0.5C7H8

M = 418.87

Triclinic,

a = 7.572 (2) Å

b = 11.259 (3) Å

c = 13.362 (3) Å

α = 69.42 (2)°

β = 86.58 (2)°

γ = 70.98 (2)°

V = 1006.3 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.22 mm−1

T = 100 K

0.3 × 0.25 × 0.1 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.990, T max = 1.000

8414 measured reflections

4154 independent reflections

2567 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.085

S = 1.02

4154 reflections

341 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.28 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811000158/dn2647sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811000158/dn2647Isup2.hkl

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

C21H18ClFO3·0.5C7H8	Z = 2
Mr = 418.87	F(000) = 438
Triclinic, P1	Dx = 1.382 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.572 (2) Å	Cell parameters from 4263 reflections
b = 11.259 (3) Å	θ = 2.9–28.2°
c = 13.362 (3) Å	µ = 0.22 mm−1
α = 69.42 (2)°	T = 100 K
β = 86.58 (2)°	Plate, colourless
γ = 70.98 (2)°	0.3 × 0.25 × 0.1 mm
V = 1006.3 (4) Å3

Oxford Diffraction Xcalibur Eos diffractometer	4154 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2567 reflections with I > 2σ(I)
graphite	Rint = 0.030
Detector resolution: 16.1544 pixels mm-1	θmax = 28.2°, θmin = 2.9°
ω scans	h = −9→10
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −14→14
Tmin = 0.990, Tmax = 1.000	l = −17→12
8414 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.032P)2] where P = (Fo2 + 2Fc2)/3
4154 reflections	(Δ/σ)max < 0.001
341 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.28 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)
C1	0.6617 (3)	0.3346 (2)	0.63392 (17)	0.0170 (5)
H1	0.553 (3)	0.4099 (19)	0.5898 (14)	0.014 (5)*
C11	0.8347 (3)	0.3354 (2)	0.57104 (17)	0.0174 (5)
O12	0.98805 (19)	0.25572 (14)	0.60237 (11)	0.0245 (4)
O13	0.79236 (18)	0.43431 (14)	0.47543 (11)	0.0194 (3)
C14	0.9412 (3)	0.4356 (3)	0.40032 (19)	0.0251 (5)
H141	0.921 (3)	0.529 (2)	0.3592 (17)	0.032 (6)*
H142	1.060 (3)	0.398 (2)	0.4422 (15)	0.020 (5)*
C15	0.9245 (4)	0.3639 (4)	0.3282 (2)	0.0443 (8)
H151	1.031 (3)	0.364 (2)	0.2731 (19)	0.047 (7)*
H152	0.939 (3)	0.267 (3)	0.369 (2)	0.052 (9)*
H153	0.812 (4)	0.395 (3)	0.290 (2)	0.063 (9)*
C2	0.6800 (3)	0.3601 (2)	0.73669 (16)	0.0173 (5)
O2	0.77611 (19)	0.42695 (14)	0.74167 (11)	0.0235 (4)
C3	0.5696 (3)	0.3083 (2)	0.82386 (17)	0.0175 (5)
H3	0.577 (3)	0.3302 (19)	0.8831 (15)	0.017 (5)*
C4	0.4587 (3)	0.23905 (19)	0.81810 (15)	0.0155 (5)
C41	0.3380 (3)	0.19687 (19)	0.90529 (16)	0.0166 (5)
C42	0.1667 (3)	0.1872 (2)	0.88281 (18)	0.0218 (5)
H42	0.132 (3)	0.2043 (19)	0.8152 (15)	0.012 (5)*
C43	0.0493 (3)	0.1525 (2)	0.96266 (17)	0.0255 (6)
H43	−0.066 (3)	0.150 (2)	0.9474 (17)	0.042 (7)*
C44	0.1033 (3)	0.1251 (2)	1.06689 (17)	0.0223 (5)
Cl44	−0.04482 (8)	0.08177 (6)	1.16805 (4)	0.03293 (18)
C45	0.2740 (3)	0.1303 (2)	1.09298 (18)	0.0203 (5)
H45	0.311 (3)	0.110 (2)	1.1647 (16)	0.021 (6)*
C46	0.3900 (3)	0.1664 (2)	1.01258 (17)	0.0187 (5)
H46	0.511 (3)	0.1664 (19)	1.0331 (14)	0.020 (5)*
C5	0.4500 (3)	0.2036 (2)	0.71992 (17)	0.0168 (5)
H51	0.339 (3)	0.2683 (19)	0.6691 (15)	0.017 (5)*
H52	0.439 (3)	0.118 (2)	0.7395 (15)	0.016 (5)*
C6	0.6248 (3)	0.2016 (2)	0.65685 (17)	0.0180 (5)
H6	0.734 (3)	0.1305 (19)	0.7046 (15)	0.017 (5)*
C61	0.6118 (3)	0.1733 (2)	0.55508 (16)	0.0159 (5)
C62	0.4812 (3)	0.2627 (2)	0.47154 (17)	0.0192 (5)
H62	0.397 (3)	0.344 (2)	0.4785 (14)	0.016 (5)*
C63	0.4697 (3)	0.2382 (2)	0.37815 (18)	0.0214 (5)
H63	0.381 (3)	0.301 (2)	0.3201 (16)	0.027 (6)*
C64	0.5913 (3)	0.1206 (2)	0.37091 (16)	0.0191 (5)
F64	0.57885 (17)	0.09459 (12)	0.27937 (9)	0.0284 (3)
C65	0.7231 (3)	0.0291 (2)	0.45003 (17)	0.0205 (5)
H65	0.803 (3)	−0.050 (2)	0.4421 (15)	0.018 (6)*
C66	0.7323 (3)	0.0571 (2)	0.54264 (17)	0.0184 (5)
H66	0.821 (3)	−0.0050 (19)	0.5957 (15)	0.011 (5)*
C1A	0.6922 (4)	0.4700 (3)	1.0220 (2)	0.0570 (8)
H1A	0.8218	0.4493	1.0377	0.068*	0.50
C11A	0.8853 (4)	0.4547 (3)	1.0355 (2)	0.0601 (17)	0.50
H11A	0.9479	0.4489	0.9703	0.072*	0.50
H11B	0.9449	0.3725	1.0962	0.072*	0.50
H11C	0.8954	0.5322	1.0494	0.072*	0.50
C2A	0.6030 (5)	0.5692 (3)	0.9267 (3)	0.0566 (8)
H2A	0.6723	0.6166	0.8762	0.068*
C3A	0.4143 (5)	0.5989 (3)	0.9052 (2)	0.0561 (8)
H3A	0.3552	0.6673	0.8400	0.067*

	U11	U22	U33	U12	U13	U23
C1	0.0164 (11)	0.0172 (12)	0.0182 (12)	−0.0066 (10)	0.0027 (9)	−0.0063 (10)
C11	0.0206 (12)	0.0163 (12)	0.0215 (13)	−0.0096 (11)	0.0015 (10)	−0.0108 (11)
O12	0.0191 (8)	0.0237 (9)	0.0271 (9)	−0.0028 (7)	0.0009 (7)	−0.0084 (7)
O13	0.0156 (8)	0.0206 (8)	0.0203 (8)	−0.0064 (7)	0.0050 (6)	−0.0051 (7)
C14	0.0183 (12)	0.0311 (15)	0.0233 (14)	−0.0107 (12)	0.0081 (10)	−0.0052 (12)
C15	0.0387 (18)	0.075 (3)	0.0380 (18)	−0.0286 (18)	0.0177 (14)	−0.0350 (18)
C2	0.0142 (11)	0.0149 (11)	0.0219 (12)	−0.0038 (10)	−0.0005 (9)	−0.0059 (10)
O2	0.0249 (8)	0.0262 (9)	0.0277 (9)	−0.0157 (8)	0.0064 (7)	−0.0135 (7)
C3	0.0190 (11)	0.0180 (12)	0.0177 (12)	−0.0063 (10)	0.0017 (9)	−0.0085 (10)
C4	0.0143 (11)	0.0127 (11)	0.0176 (12)	−0.0032 (9)	0.0007 (9)	−0.0040 (9)
C41	0.0160 (11)	0.0128 (11)	0.0185 (12)	−0.0023 (10)	0.0020 (9)	−0.0050 (10)
C42	0.0217 (12)	0.0268 (13)	0.0148 (13)	−0.0088 (11)	−0.0009 (10)	−0.0035 (11)
C43	0.0144 (12)	0.0354 (15)	0.0234 (14)	−0.0099 (11)	0.0011 (10)	−0.0048 (12)
C44	0.0220 (12)	0.0228 (13)	0.0207 (13)	−0.0081 (10)	0.0068 (10)	−0.0061 (11)
Cl44	0.0256 (3)	0.0469 (4)	0.0230 (3)	−0.0148 (3)	0.0094 (2)	−0.0070 (3)
C45	0.0239 (12)	0.0205 (13)	0.0146 (13)	−0.0051 (10)	0.0001 (10)	−0.0059 (10)
C46	0.0184 (12)	0.0173 (12)	0.0218 (13)	−0.0068 (10)	−0.0006 (10)	−0.0073 (10)
C5	0.0179 (12)	0.0165 (12)	0.0173 (12)	−0.0081 (10)	0.0019 (9)	−0.0053 (10)
C6	0.0167 (11)	0.0194 (12)	0.0209 (12)	−0.0073 (10)	0.0017 (9)	−0.0095 (10)
C61	0.0149 (11)	0.0176 (12)	0.0187 (12)	−0.0103 (10)	0.0050 (9)	−0.0065 (10)
C62	0.0161 (11)	0.0180 (12)	0.0269 (13)	−0.0075 (10)	0.0051 (9)	−0.0107 (11)
C63	0.0178 (12)	0.0243 (13)	0.0216 (13)	−0.0080 (11)	−0.0005 (10)	−0.0063 (11)
C64	0.0227 (12)	0.0293 (13)	0.0160 (12)	−0.0183 (11)	0.0084 (9)	−0.0128 (10)
F64	0.0349 (8)	0.0383 (8)	0.0244 (7)	−0.0190 (7)	0.0084 (6)	−0.0202 (6)
C65	0.0184 (12)	0.0182 (12)	0.0285 (14)	−0.0083 (11)	0.0100 (10)	−0.0118 (11)
C66	0.0162 (11)	0.0167 (12)	0.0190 (12)	−0.0049 (10)	0.0000 (9)	−0.0028 (10)
C1A	0.061 (2)	0.064 (2)	0.065 (2)	−0.0231 (19)	0.0106 (18)	−0.043 (2)
C11A	0.052 (4)	0.060 (4)	0.071 (4)	−0.007 (3)	−0.001 (3)	−0.035 (4)
C2A	0.065 (2)	0.060 (2)	0.061 (2)	−0.0264 (19)	0.0088 (18)	−0.0355 (19)
C3A	0.073 (2)	0.052 (2)	0.055 (2)	−0.0239 (19)	0.0092 (17)	−0.0289 (17)

C1—C11	1.514 (3)	C46—H46	0.973 (19)
C1—C2	1.520 (3)	C5—C6	1.524 (3)
C1—C6	1.534 (3)	C5—H51	1.01 (2)
C1—H1	0.996 (19)	C5—H52	0.938 (19)
C11—O12	1.202 (2)	C6—C61	1.517 (3)
C11—O13	1.338 (2)	C6—H6	1.003 (19)
O13—C14	1.464 (2)	C61—C66	1.389 (3)
C14—C15	1.491 (3)	C61—C62	1.390 (3)
C14—H141	0.97 (2)	C62—C63	1.383 (3)
C14—H142	0.98 (2)	C62—H62	0.96 (2)
C15—H151	1.06 (2)	C63—C64	1.377 (3)
C15—H152	1.01 (3)	C63—H63	0.96 (2)
C15—H153	0.91 (3)	C64—C65	1.366 (3)
C2—O2	1.225 (2)	C64—F64	1.369 (2)
C2—C3	1.456 (3)	C65—C66	1.391 (3)
C3—C4	1.340 (3)	C65—H65	0.94 (2)
C3—H3	0.918 (19)	C66—H66	0.921 (19)
C4—C41	1.478 (3)	C1A—C2A	1.392 (4)
C4—C5	1.510 (3)	C1A—C3Ai	1.408 (4)
C41—C42	1.395 (3)	C1A—C11A	1.4305
C41—C46	1.401 (3)	C1A—H1A	0.9500
C42—C43	1.379 (3)	C11A—H11A	0.9800
C42—H42	0.892 (18)	C11A—H11B	0.9800
C43—C44	1.373 (3)	C11A—H11C	0.9800
C43—H43	0.92 (2)	C2A—C3A	1.381 (4)
C44—C45	1.383 (3)	C2A—H2A	0.9500
C44—Cl44	1.742 (2)	C3A—C1Ai	1.408 (4)
C45—C46	1.380 (3)	C3A—H3A	0.9500
C45—H45	0.94 (2)
C11—C1—C2	111.06 (17)	C41—C46—H46	121.1 (11)
C11—C1—C6	110.02 (17)	C4—C5—C6	112.59 (17)
C2—C1—C6	111.44 (17)	C4—C5—H51	112.3 (11)
C11—C1—H1	108.1 (10)	C6—C5—H51	107.3 (10)
C2—C1—H1	107.0 (10)	C4—C5—H52	110.4 (12)
C6—C1—H1	109.1 (10)	C6—C5—H52	107.0 (11)
O12—C11—O13	124.93 (18)	H51—C5—H52	107.0 (15)
O12—C11—C1	124.19 (19)	C61—C6—C5	112.59 (17)
O13—C11—C1	110.86 (17)	C61—C6—C1	111.90 (17)
C11—O13—C14	116.65 (16)	C5—C6—C1	108.92 (17)
O13—C14—C15	109.77 (18)	C61—C6—H6	109.7 (11)
O13—C14—H141	105.4 (12)	C5—C6—H6	107.8 (10)
C15—C14—H141	110.0 (13)	C1—C6—H6	105.6 (10)
O13—C14—H142	107.7 (11)	C66—C61—C62	118.12 (19)
C15—C14—H142	114.2 (12)	C66—C61—C6	120.58 (19)
H141—C14—H142	109.3 (17)	C62—C61—C6	121.30 (19)
C14—C15—H151	110.8 (12)	C63—C62—C61	121.6 (2)
C14—C15—H152	111.7 (15)	C63—C62—H62	119.0 (11)
H151—C15—H152	106.4 (19)	C61—C62—H62	119.4 (11)
C14—C15—H153	116.4 (17)	C64—C63—C62	117.7 (2)
H151—C15—H153	108 (2)	C64—C63—H63	121.0 (12)
H152—C15—H153	103 (2)	C62—C63—H63	121.4 (12)
O2—C2—C3	123.01 (19)	C65—C64—F64	118.58 (19)
O2—C2—C1	120.32 (18)	C65—C64—C63	123.4 (2)
C3—C2—C1	116.57 (18)	F64—C64—C63	118.0 (2)
C4—C3—C2	123.6 (2)	C64—C65—C66	117.6 (2)
C4—C3—H3	121.6 (12)	C64—C65—H65	120.7 (12)
C2—C3—H3	114.7 (12)	C66—C65—H65	121.6 (12)
C3—C4—C41	122.00 (18)	C61—C66—C65	121.6 (2)
C3—C4—C5	120.58 (18)	C61—C66—H66	121.2 (12)
C41—C4—C5	117.40 (17)	C65—C66—H66	117.2 (12)
C42—C41—C46	117.75 (18)	C2A—C1A—C3Ai	118.4 (3)
C42—C41—C4	120.68 (18)	C2A—C1A—C11A	114.00 (18)
C46—C41—C4	121.57 (18)	C3Ai—C1A—C11A	127.52 (19)
C43—C42—C41	121.5 (2)	C2A—C1A—H1A	120.8
C43—C42—H42	119.0 (12)	C3Ai—C1A—H1A	120.8
C41—C42—H42	119.5 (12)	C1A—C11A—H11A	109.5
C44—C43—C42	119.3 (2)	C1A—C11A—H11B	109.5
C44—C43—H43	119.2 (14)	H11A—C11A—H11B	109.5
C42—C43—H43	121.4 (14)	C1A—C11A—H11C	109.5
C43—C44—C45	121.08 (19)	H11A—C11A—H11C	109.5
C43—C44—Cl44	119.46 (16)	H11B—C11A—H11C	109.5
C45—C44—Cl44	119.46 (17)	C3A—C2A—C1A	120.3 (3)
C46—C45—C44	119.4 (2)	C3A—C2A—H2A	119.9
C46—C45—H45	119.9 (12)	C1A—C2A—H2A	119.9
C44—C45—H45	120.7 (12)	C2A—C3A—C1Ai	121.3 (3)
C45—C46—C41	121.0 (2)	C2A—C3A—H3A	119.4
C45—C46—H46	117.9 (11)	C1Ai—C3A—H3A	119.4
C2—C1—C11—O12	63.8 (3)	C42—C41—C46—C45	−1.1 (3)
C6—C1—C11—O12	−60.1 (3)	C4—C41—C46—C45	178.40 (19)
C2—C1—C11—O13	−117.79 (19)	C3—C4—C5—C6	23.3 (3)
C6—C1—C11—O13	118.35 (18)	C41—C4—C5—C6	−157.89 (18)
O12—C11—O13—C14	6.5 (3)	C4—C5—C6—C61	−176.97 (18)
C1—C11—O13—C14	−171.86 (17)	C4—C5—C6—C1	−52.3 (2)
C11—O13—C14—C15	94.2 (3)	C11—C1—C6—C61	−54.7 (2)
C11—C1—C2—O2	28.6 (3)	C2—C1—C6—C61	−178.39 (17)
C6—C1—C2—O2	151.70 (18)	C11—C1—C6—C5	−179.88 (17)
C11—C1—C2—C3	−154.95 (18)	C2—C1—C6—C5	56.5 (2)
C6—C1—C2—C3	−31.9 (3)	C5—C6—C61—C66	−115.4 (2)
O2—C2—C3—C4	177.6 (2)	C1—C6—C61—C66	121.5 (2)
C1—C2—C3—C4	1.3 (3)	C5—C6—C61—C62	65.2 (2)
C2—C3—C4—C41	−175.33 (19)	C1—C6—C61—C62	−57.9 (2)
C2—C3—C4—C5	3.4 (3)	C66—C61—C62—C63	0.0 (3)
C3—C4—C41—C42	148.1 (2)	C6—C61—C62—C63	179.37 (18)
C5—C4—C41—C42	−30.6 (3)	C61—C62—C63—C64	0.8 (3)
C3—C4—C41—C46	−31.4 (3)	C62—C63—C64—C65	−1.1 (3)
C5—C4—C41—C46	149.9 (2)	C62—C63—C64—F64	179.03 (16)
C46—C41—C42—C43	1.8 (3)	F64—C64—C65—C66	−179.54 (16)
C4—C41—C42—C43	−177.7 (2)	C63—C64—C65—C66	0.5 (3)
C41—C42—C43—C44	−0.9 (3)	C62—C61—C66—C65	−0.5 (3)
C42—C43—C44—C45	−0.7 (3)	C6—C61—C66—C65	−179.92 (18)
C42—C43—C44—Cl44	179.81 (17)	C64—C65—C66—C61	0.3 (3)
C43—C44—C45—C46	1.3 (3)	C3Ai—C1A—C2A—C3A	0.4 (4)
Cl44—C44—C45—C46	−179.14 (16)	C11A—C1A—C2A—C3A	−177.18 (19)
C44—C45—C46—C41	−0.4 (3)	C1A—C2A—C3A—C1Ai	−0.4 (4)

Cg is the centroid of the C1A–C3A,C1A'–C3A' ring.

D—H···A	D—H	H···A	D···A	D—H···A
C45—H45···F64ii	0.94 (2)	2.54 (2)	3.327 (3)	141.6 (15)
C5—H52···F64iii	0.938 (19)	2.54 (2)	3.432 (3)	159.3 (15)
C6—H6···Cl44iv	1.003 (19)	2.84 (2)	3.846 (3)	176.3 (14)
C65—H65···O12v	0.94 (2)	2.59 (2)	3.519 (3)	173.6 (16)
C3—H3···Cg	0.918 (19)	2.78 (2)	3.627 (3)	155.0 (17)
C3—H3···Cgi	0.918 (19)	2.78 (2)	3.627 (3)	155.0 (17)

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1A–C3A,C1A′–C3A′ ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C45—H45⋯F64i	0.94 (2)	2.54 (2)	3.327 (3)	141.6 (15)
C5—H52⋯F64ii	0.938 (19)	2.54 (2)	3.432 (3)	159.3 (15)
C6—H6⋯Cl44iii	1.003 (19)	2.84 (2)	3.846 (3)	176.3 (14)
C65—H65⋯O12iv	0.94 (2)	2.59 (2)	3.519 (3)	173.6 (16)
C3—H3⋯Cg	0.918 (19)	2.78 (2)	3.627 (3)	155.0 (17)
C3—H3⋯Cgv	0.918 (19)	2.78 (2)	3.627 (3)	155.0 (17)

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