1:1 Complexes of 2,3,5,6-tetrachloro­benzene-1,4-dicarbonitrile with pyrene and phenanthrene: pseudo-isomorphs

2,3,5,6-Tetra­chloro­benzene-1,4-dicarbonitrile forms alternate π-stacked 1:1 complexes with pyrene, C₈Cl₄N₂·C₁₆H₁₀, and phenanthrene, C₈Cl₄N₂·C₁₄H₁₀. These complexes are pseudo-isomorphs. Phenanthrene, disordered about a centre of symmetry, takes the position of the pyrene, which sits exactly on this centre of inversion. The tetra­chloro­benzene­di­car­bo­nitrile mol­ecules in each complex also sit on centres of inversion and are in similar positions within the unit cells in the two structures, except that the orientation of the nitrile groups differs between the two.

S1. Comment

In an earlier paper (Britton, 2002), the formation of two-dimensional arrays of the isomers of tetrachlorodicyanobenzene, TCDB, by formation of complexes with hexamethylbenzene was described. At the same time, the possibility of forming similar arrangements, with other π bases replacing the hexamethylbenzene, was explored. While a number of complexes were formed, none of them had the desired layers of TCDB. The structures of two of these complexes, p-TCDB–pyrene (1/1), (I), and p-TCDB–phenanthrene (1/1), (II), are described here.

Fig. 1 shows the labelling and anisotropic displacement ellipsoids for the molecules in (I). Both molecules lie on centres of symmetry. Fig. 2 shows the labelling and anisotropic displacement ellipsoids for the molecules in (II). The TCDB molecules lie on one centre of symmetry and the phenanthrene molecules are disordered about another. Fig. 2 shows the relative positions of the disordered phenanthrene molecules with respect to each other. In both Figs. 1 and 2, the view is along a with b vertical. Although the structures are otherwise similar, the orientation of the nitrile groups is different in the two structures; the molecules are rotated approximately 60° in the plane of the molecule with respect to each other. To the extent that bond lengths and angles were measured, they are normal in both structures.

The primary intermolecular interactions in both of these complexes are π stacks of alternating molecules parallel to the a axis. The molecules are tilted 3.2° away from parallel with each other in (I), and 2.8° in (II). The molecules are 3.43 (12) Å apart in (I) and 3.44 (10) Å apart in (II); the large uncertainties are a consequence of the deviations from parallel.

In both structures, the molecules also lie in puckered layers parallel to (100). In Fig. 3, one such layer is shown for (I). The TCDB molecules are tilted by 18.3 (1)° and the pyrene molecules by 19.0 (1)° with respect to (100); the two molecules are tilted by 24.6 (1)° with respect to each other. The corresponding tilts in (II) are 26.8 (1), 25.3 (1) and 35.3 (1)°, respectively. The layers appear to be held together by weak C—H hydrogen bonds; these are shown in Fig. 3. The geometric data are given in Table 1. There are similar interactions in (II) but, in view of the disorder shown in Fig. 2 and the additional untreated disorder that must be present in the TCDB atomic positions, the geometric data for these interactions have not been included. The disorder of the TCDB molecules in (II) can be seen from the larger atomic displacement parameters for this moiety in Fig. 2, compared with those in Fig. 1. This disorder arises from the disorder in the adjacent phenanthrene molecules and must consist of small displacements in various directions that depend on the particular orientations of all the surrounding phenanthrene molecules; it does not seem worthwhile to attempt to model this disorder.

In the two structures, the unit cells are similar and the packings are similar, but, as mentioned above, the orientations of the TCDB molecules are different. They are probably best described as pseudo-isomorphs.

S2. Experimental

Crystals of both complexes were obtained by dissolving equimolar quantities of the two components in acetone and allowing the solutions to evaporate.

S3. Refinement

For (II), when the disorder of the phenanthrene molecule around the centre of symmetry at (1/2, 1/2, 1) was found, the molecule was restrained using DFIX (Sheldrick, 1997) to have the average bond lengths and angles found by Petříček et al. (1990). When the disordered orientations are superimposed, some of the atoms of the symmetry-related orientation are close to overlapping with those of the first orientation. Atoms that resulted in such overlap were constrained to have identical ADP's. Under these conditions, the refinement proceeded satisfactorily.

Computing details

For both compounds, data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures

	Fig. 1. Both molecules in TCDB–pyrene, (I). Displacement ellipsoids are shown at the 50% probability level. Only the symmetry-independent atoms are labelled. The view is down a with b vertical.
	Fig. 2. Both molecules in TCDB–phenanthrene, (II), including the disordered components (thinner bonds). Displacement ellipsoids are shown at the 50% probability level. Only the symmetry-independent atoms are labelled. The view is from the same direction and orientation as in Fig. 1.
	Fig. 3. The packing in compound (I), viewed down a, showing one layer of molecules approximately parallel to (100). Weak hydrogen bonds are shown as dotted lines. The molecules alternate in π stacks parallel to a.

(I) 2,3,5,6-tetrachlorobenzene-1,4-dicarbonitrile–pyrene (1/1)

Crystal data

C8Cl4N2·C16H10	F(000) = 472
Mr = 468.14	Dx = 1.598 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3295 reflections
a = 7.0679 (18) Å	θ = 2.5–25.0°
b = 15.983 (4) Å	µ = 0.62 mm^−1
c = 8.907 (2) Å	T = 174 K
β = 104.78 (1)°	Needle, yellow
V = 972.9 (4) Å^3	0.35 × 0.12 × 0.05 mm
Z = 2

Data collection

Siemens SMART area-detector diffractometer	1700 independent reflections
Radiation source: fine-focus sealed tube	1474 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
ω scans	θmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996; Blessing, 1995)	h = −8→8
Tmin = 0.91, Tmax = 0.97	k = −12→18
4778 measured reflections	l = −10→8

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.081	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.043P)^2 + 0.306P] where P = (Fo^2 + 2Fc^2)/3
1700 reflections	(Δ/σ)max = 0.001
136 parameters	Δρmax = 0.29 e Å^−3
0 restraints	Δρmin = −0.21 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl2	0.13500 (8)	0.41473 (3)	0.32493 (5)	0.03111 (17)
Cl3	−0.05569 (8)	0.39078 (3)	−0.29796 (5)	0.03045 (17)
N1	0.1190 (3)	0.25608 (12)	0.0300 (2)	0.0367 (5)
C1	0.0411 (3)	0.41494 (12)	0.0117 (2)	0.0223 (4)
C2	0.0624 (3)	0.46237 (12)	0.1466 (2)	0.0231 (4)
C3	−0.0226 (3)	0.45202 (12)	−0.1355 (2)	0.0230 (4)
C4	0.0844 (3)	0.32604 (13)	0.0226 (2)	0.0267 (5)
C11	0.6324 (3)	0.28826 (14)	1.0510 (3)	0.0363 (5)
H11	0.6694	0.2311	1.0649	0.044*
C12	0.5703 (3)	0.32052 (13)	0.9021 (3)	0.0329 (5)
H12	0.5643	0.2852	0.8151	0.040*
C13	0.5164 (3)	0.40472 (12)	0.8789 (2)	0.0264 (5)
C14	0.5265 (3)	0.45663 (13)	1.0103 (2)	0.0229 (4)
C15	0.5891 (3)	0.42292 (13)	1.1632 (2)	0.0273 (5)
C16	0.6413 (3)	0.33793 (14)	1.1800 (3)	0.0329 (5)
H16	0.6832	0.3143	1.2809	0.040*
C17	0.4529 (3)	0.44142 (14)	0.7266 (2)	0.0303 (5)
H17	0.4464	0.4074	0.6379	0.036*
C18	0.5976 (3)	0.47722 (14)	1.2933 (2)	0.0317 (5)
H18	0.6398	0.4553	1.3956	0.038*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl2	0.0353 (3)	0.0329 (3)	0.0221 (3)	−0.0021 (2)	0.0017 (2)	0.0062 (2)
Cl3	0.0345 (3)	0.0317 (3)	0.0240 (3)	−0.0007 (2)	0.0053 (2)	−0.0063 (2)
N1	0.0465 (12)	0.0301 (11)	0.0341 (10)	0.0079 (9)	0.0113 (9)	0.0028 (8)
C1	0.0163 (10)	0.0234 (10)	0.0266 (10)	−0.0023 (8)	0.0041 (8)	0.0007 (8)
C2	0.0183 (10)	0.0279 (11)	0.0215 (10)	−0.0025 (8)	0.0019 (7)	0.0032 (8)
C3	0.0179 (10)	0.0276 (10)	0.0229 (10)	−0.0033 (8)	0.0041 (8)	−0.0032 (8)
C4	0.0254 (11)	0.0305 (12)	0.0236 (10)	0.0009 (9)	0.0052 (8)	0.0010 (8)
C11	0.0317 (12)	0.0267 (12)	0.0539 (15)	0.0008 (9)	0.0173 (11)	0.0062 (10)
C12	0.0289 (12)	0.0286 (12)	0.0446 (13)	−0.0050 (9)	0.0153 (10)	−0.0058 (10)
C13	0.0176 (10)	0.0310 (11)	0.0308 (11)	−0.0059 (8)	0.0064 (8)	−0.0022 (8)
C14	0.0141 (9)	0.0293 (10)	0.0255 (10)	−0.0019 (8)	0.0055 (8)	0.0016 (8)
C15	0.0195 (10)	0.0346 (12)	0.0279 (11)	−0.0025 (9)	0.0063 (8)	0.0042 (9)
C16	0.0254 (11)	0.0357 (12)	0.0377 (12)	0.0019 (9)	0.0080 (9)	0.0136 (10)
C17	0.0259 (11)	0.0408 (13)	0.0243 (10)	−0.0058 (9)	0.0065 (9)	−0.0069 (9)
C18	0.0248 (11)	0.0454 (14)	0.0229 (11)	−0.0031 (9)	0.0026 (8)	0.0045 (9)

Geometric parameters (Å, º)

Cl2—C2	1.7178 (19)	C12—H12	0.9500
Cl3—C3	1.7132 (19)	C13—C14	1.421 (3)
N1—C4	1.143 (3)	C13—C17	1.441 (3)
C1—C2	1.396 (3)	C14—C15	1.426 (3)
C1—C3	1.404 (3)	C14—C14^ii	1.435 (4)
C1—C4	1.452 (3)	C15—C16	1.406 (3)
C2—C3^i	1.395 (3)	C15—C18	1.437 (3)
C11—C16	1.384 (3)	C16—H16	0.9500
C11—C12	1.386 (3)	C17—C18^ii	1.348 (3)
C11—H11	0.9500	C17—H17	0.9500
C12—C13	1.399 (3)	C18—H18	0.9500
C2—C1—C3	120.85 (17)	C12—C13—C17	122.53 (19)
C2—C1—C4	119.98 (17)	C14—C13—C17	118.41 (18)
C3—C1—C4	119.17 (17)	C13—C14—C15	120.24 (18)
C1—C2—C3^i	119.73 (17)	C13—C14—C14^ii	120.1 (2)
C1—C2—Cl2	119.76 (15)	C15—C14—C14^ii	119.6 (2)
C3^i—C2—Cl2	120.50 (14)	C16—C15—C14	118.44 (19)
C2^i—C3—C1	119.41 (17)	C16—C15—C18	122.81 (18)
C2^i—C3—Cl3	121.24 (14)	C14—C15—C18	118.75 (18)
C1—C3—Cl3	119.33 (15)	C11—C16—C15	120.71 (19)
N1—C4—C1	179.4 (2)	C11—C16—H16	119.6
C16—C11—C12	121.1 (2)	C15—C16—H16	119.6
C16—C11—H11	119.4	C18^ii—C17—C13	121.65 (19)
C12—C11—H11	119.4	C18^ii—C17—H17	119.2
C11—C12—C13	120.4 (2)	C13—C17—H17	119.2
C11—C12—H12	119.8	C17^ii—C18—C15	121.43 (18)
C13—C12—H12	119.8	C17^ii—C18—H18	119.3
C12—C13—C14	119.05 (19)	C15—C18—H18	119.3
C3—C1—C2—C3^i	−0.9 (3)	C12—C13—C14—C14^ii	179.5 (2)
C4—C1—C2—C3^i	179.28 (17)	C17—C13—C14—C14^ii	0.2 (3)
C3—C1—C2—Cl2	178.44 (14)	C13—C14—C15—C16	0.4 (3)
C4—C1—C2—Cl2	−1.4 (2)	C14^ii—C14—C15—C16	−179.6 (2)
C2—C1—C3—C2^i	0.9 (3)	C13—C14—C15—C18	179.94 (18)
C4—C1—C3—C2^i	−179.28 (17)	C14^ii—C14—C15—C18	0.0 (3)
C2—C1—C3—Cl3	−177.55 (14)	C12—C11—C16—C15	−0.6 (3)
C4—C1—C3—Cl3	2.3 (2)	C14—C15—C16—C11	0.1 (3)
C16—C11—C12—C13	0.5 (3)	C18—C15—C16—C11	−179.40 (19)
C11—C12—C13—C14	0.0 (3)	C12—C13—C17—C18^ii	−179.7 (2)
C11—C12—C13—C17	179.36 (18)	C14—C13—C17—C18^ii	−0.4 (3)
C12—C13—C14—C15	−0.5 (3)	C16—C15—C18—C17^ii	179.8 (2)
C17—C13—C14—C15	−179.84 (17)	C14—C15—C18—C17^ii	0.3 (3)

Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, −y+1, −z+2.

(II) 2,3,5,6-tetrachlorobenzene-1,4-dicarbonitrile–phenanthrene (1/1)

Crystal data

C8Cl4N2·C14H10	F(000) = 448
Mr = 444.12	Dx = 1.547 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3496 reflections
a = 7.1731 (18) Å	θ = 2.6–25.0°
b = 15.599 (4) Å	µ = 0.63 mm^−1
c = 9.104 (2) Å	T = 174 K
β = 110.60 (1)°	Needle, yellow
V = 953.5 (4) Å^3	0.40 × 0.20 × 0.12 mm
Z = 2

Data collection

Siemens SMART area-detector diffractometer	1667 independent reflections
Radiation source: fine-focus sealed tube	1415 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
ω scans	θmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan SADABS (Sheldrick, 1996; Blessing, 1995)	h = −8→8
Tmin = 0.86, Tmax = 0.93	k = −11→18
4557 measured reflections	l = −10→10

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.115	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.057P)^2 + 0.66P] where P = (Fo^2 + 2Fc^2)/3
1667 reflections	(Δ/σ)max = 0.001
154 parameters	Δρmax = 0.30 e Å^−3
35 restraints	Δρmin = −0.42 e Å^−3

Special details

Refinement. The bond lengths and angles in the phenanthrene were constrained to equal those of Petricek et al. (1990).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl2	0.6418 (7)	0.3104 (3)	0.0336 (7)	0.0543 (18)
Cl3	0.4391 (8)	0.3915 (4)	−0.2990 (7)	0.064 (2)
N1	0.758 (4)	0.3990 (15)	0.420 (3)	0.086 (7)
C1	0.590 (2)	0.4642 (10)	0.148 (2)	0.039 (4)
C2	0.563 (2)	0.4146 (10)	0.014 (2)	0.038 (4)
C3	0.473 (2)	0.4506 (11)	−0.134 (2)	0.038 (4)
C4	0.689 (3)	0.4259 (11)	0.306 (2)	0.043 (4)
C11	1.056 (3)	0.4614 (15)	1.059 (2)	0.026 (6)	0.50
C12	1.137 (3)	0.4326 (16)	1.2134 (19)	0.032 (8)	0.50
H12	1.1432	0.4702	1.2973	0.038*	0.50
C13	1.208 (4)	0.3502 (18)	1.245 (3)	0.044 (9)	0.50
H13	1.2627	0.3315	1.3511	0.053*	0.50
C14	1.200 (4)	0.2941 (15)	1.126 (4)	0.042 (9)	0.50
H14	1.2491	0.2373	1.1495	0.051*	0.50
C15	1.122 (4)	0.3204 (19)	0.975 (3)	0.035 (8)	0.50
H15	1.1163	0.2816	0.8934	0.042*	0.50
C16	1.048 (4)	0.405 (2)	0.937 (2)	0.032 (8)	0.50
C17	0.966 (3)	0.4305 (14)	0.775 (3)	0.036 (7)	0.50
H17	0.9613	0.3914	0.6944	0.044*	0.50
C18	0.895 (3)	0.5102 (16)	0.740 (2)	0.035 (7)	0.50
H18	0.8413	0.5263	0.6328	0.043*	0.50
C19	0.897 (4)	0.5723 (18)	0.856 (2)	0.032 (8)	0.50
C20	0.820 (4)	0.6564 (19)	0.813 (3)	0.044 (9)	0.50
H20	0.7666	0.6719	0.7049	0.053*	0.50
C21	0.823 (4)	0.7148 (16)	0.924 (4)	0.042 (9)	0.50
H21	0.7717	0.7705	0.8918	0.051*	0.50
C22	0.899 (4)	0.6960 (16)	1.084 (4)	0.035 (8)	0.50
H22	0.9006	0.7372	1.1616	0.042*	0.50
C23	0.974 (4)	0.6122 (17)	1.125 (2)	0.032 (8)	0.50
H23	1.0270	0.5982	1.2334	0.038*	0.50
C24	0.978 (3)	0.5471 (14)	1.016 (2)	0.026 (6)	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl2	0.046 (3)	0.030 (2)	0.098 (4)	0.0036 (17)	0.040 (3)	0.001 (2)
Cl3	0.064 (3)	0.062 (4)	0.073 (4)	−0.007 (2)	0.034 (3)	−0.024 (3)
N1	0.082 (15)	0.082 (16)	0.093 (16)	−0.007 (12)	0.031 (13)	0.020 (13)
C1	0.029 (8)	0.037 (9)	0.055 (10)	−0.005 (7)	0.022 (7)	−0.001 (7)
C2	0.029 (8)	0.029 (8)	0.064 (11)	−0.004 (6)	0.026 (8)	−0.003 (7)
C3	0.032 (8)	0.036 (9)	0.055 (10)	−0.007 (7)	0.025 (8)	−0.010 (7)
C4	0.041 (9)	0.039 (9)	0.054 (11)	−0.006 (8)	0.024 (9)	0.002 (8)
C11	0.019 (11)	0.032 (12)	0.025 (19)	−0.004 (9)	0.007 (15)	0.007 (16)
C12	0.031 (13)	0.034 (11)	0.03 (2)	−0.003 (9)	0.013 (16)	0.002 (16)
C13	0.033 (12)	0.039 (12)	0.06 (3)	0.003 (10)	0.016 (15)	0.019 (16)
C14	0.033 (11)	0.026 (11)	0.07 (3)	0.001 (9)	0.019 (15)	0.008 (13)
C15	0.030 (11)	0.019 (14)	0.06 (3)	−0.006 (9)	0.020 (15)	−0.017 (14)
C16	0.024 (10)	0.026 (15)	0.05 (2)	−0.004 (9)	0.015 (14)	−0.004 (16)
C17	0.034 (16)	0.035 (18)	0.039 (17)	−0.007 (14)	0.012 (14)	−0.009 (14)
C18	0.030 (16)	0.04 (2)	0.028 (15)	−0.007 (14)	0.005 (13)	0.000 (13)
C19	0.031 (13)	0.034 (11)	0.03 (2)	−0.003 (9)	0.013 (16)	0.002 (16)
C20	0.033 (12)	0.039 (12)	0.06 (3)	0.003 (10)	0.016 (15)	0.019 (16)
C21	0.033 (11)	0.026 (11)	0.07 (3)	0.001 (9)	0.019 (15)	0.008 (13)
C22	0.030 (11)	0.019 (14)	0.06 (3)	−0.006 (9)	0.020 (15)	−0.017 (14)
C23	0.024 (10)	0.026 (15)	0.05 (2)	−0.004 (9)	0.015 (14)	−0.004 (16)
C24	0.019 (11)	0.032 (12)	0.025 (19)	−0.004 (9)	0.007 (15)	0.007 (16)

Geometric parameters (Å, º)

Cl2—C2	1.709 (16)	C15—H15	0.9500
Cl3—C3	1.709 (16)	C16—C17	1.43 (3)
N1—C4	1.07 (3)	C17—C18	1.338 (7)
C1—C3^i	1.39 (2)	C17—H17	0.9500
C1—C2	1.40 (2)	C18—C19	1.43 (3)
C1—C4	1.49 (3)	C18—H18	0.9500
C2—C3	1.39 (2)	C19—C20	1.422 (7)
C11—C12	1.390 (6)	C19—C24	1.425 (7)
C11—C16	1.410 (6)	C20—C21	1.357 (7)
C11—C24	1.449 (7)	C20—H20	0.9500
C12—C13	1.376 (7)	C21—C22	1.398 (7)
C12—H12	0.9500	C21—H21	0.9500
C13—C14	1.381 (7)	C22—C23	1.413 (7)
C13—H13	0.9500	C22—H22	0.9500
C14—C15	1.350 (7)	C23—C24	1.424 (7)
C14—H14	0.9500	C23—H23	0.9500
C15—C16	1.414 (7)
C3^i—C1—C2	120.4 (16)	C15—C16—C17	120 (2)
C3^i—C1—C4	120.1 (15)	C11—C16—C17	121 (2)
C2—C1—C4	119.5 (15)	C18—C17—C16	119 (2)
C3—C2—C1	119.5 (15)	C18—C17—H17	120.3
C3—C2—Cl2	120.8 (13)	C16—C17—H17	120.3
C1—C2—Cl2	119.7 (14)	C17—C18—C19	123 (2)
C2—C3—C1^i	120.1 (15)	C17—C18—H18	118.3
C2—C3—Cl3	120.4 (13)	C19—C18—H18	118.3
C1^i—C3—Cl3	119.5 (14)	C20—C19—C24	121.1 (7)
N1—C4—C1	179 (2)	C20—C19—C18	121.4 (18)
C12—C11—C16	118.9 (6)	C24—C19—C18	117.5 (19)
C12—C11—C24	123.8 (18)	C21—C20—C19	120.6 (7)
C16—C11—C24	117.4 (18)	C21—C20—H20	119.7
C13—C12—C11	120.4 (7)	C19—C20—H20	119.7
C13—C12—H12	119.8	C20—C21—C22	122.6 (8)
C11—C12—H12	119.8	C20—C21—H21	118.7
C12—C13—C14	121.1 (9)	C22—C21—H21	118.7
C12—C13—H13	119.4	C21—C22—C23	116.1 (8)
C14—C13—H13	119.4	C21—C22—H22	122.0
C15—C14—C13	119.6 (7)	C23—C22—H22	122.0
C15—C14—H14	120.2	C22—C23—C24	125.2 (6)
C13—C14—H14	120.2	C22—C23—H23	117.4
C14—C15—C16	121.3 (6)	C24—C23—H23	117.4
C14—C15—H15	119.3	C19—C24—C11	120.8 (17)
C16—C15—H15	119.3	C19—C24—C23	114.5 (7)
C15—C16—C11	118.7 (7)	C11—C24—C23	124.6 (17)
C3^i—C1—C2—C3	−1 (2)	C11—C16—C17—C18	0 (3)
C4—C1—C2—C3	−179.1 (14)	C16—C17—C18—C19	0 (3)
C3^i—C1—C2—Cl2	179.8 (11)	C17—C18—C19—C20	179.9 (18)
C4—C1—C2—Cl2	1 (2)	C17—C18—C19—C24	0 (3)
C1—C2—C3—C1^i	1 (2)	C24—C19—C20—C21	0 (3)
Cl2—C2—C3—C1^i	−179.8 (11)	C18—C19—C20—C21	−179.8 (18)
C1—C2—C3—Cl3	180.0 (11)	C19—C20—C21—C22	0 (3)
Cl2—C2—C3—Cl3	−0.3 (19)	C20—C21—C22—C23	0 (3)
C16—C11—C12—C13	−0.1 (9)	C21—C22—C23—C24	0 (3)
C24—C11—C12—C13	179.9 (9)	C20—C19—C24—C11	−179.9 (15)
C11—C12—C13—C14	−0.1 (10)	C18—C19—C24—C11	0 (3)
C12—C13—C14—C15	0 (2)	C20—C19—C24—C23	0 (3)
C13—C14—C15—C16	0 (3)	C18—C19—C24—C23	180.0 (17)
C14—C15—C16—C11	0 (3)	C12—C11—C24—C19	180.0 (12)
C14—C15—C16—C17	180.0 (18)	C16—C11—C24—C19	0 (2)
C12—C11—C16—C15	0.3 (19)	C12—C11—C24—C23	0 (2)
C24—C11—C16—C15	−179.7 (15)	C16—C11—C24—C23	−179.9 (18)
C12—C11—C16—C17	180.0 (13)	C22—C23—C24—C19	0 (3)
C24—C11—C16—C17	0 (2)	C22—C23—C24—C11	179.8 (16)
C15—C16—C17—C18	179.7 (18)

Symmetry code: (i) −x+1, −y+1, −z.