5,8,13,13-Tetra­chloro-13H-dibenzo[a,i]fluorene cyclo­hexane hemisolvate

Detert, H.; Schollmeyer, D.

doi:10.1107/S2414314619002360

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 4| Part 2| February 2019| x190236

https://doi.org/10.1107/S2414314619002360

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5,8,13,13-Tetrachloro-13H-dibenzo[a,i]fluorene cyclohexane hemisolvate

Heiner Detert ^a ^* and Dieter Schollmeyer ^a

^aUniversity of Mainz, Institute of Organic Chemistry, Duesbergweg 10-14, 55099 Mainz, Germany
^*Correspondence e-mail: detert@uni-mainz.de

Edited by M. Bolte, Goethe-Universität Frankfurt, Germany (Received 12 February 2019; accepted 15 February 2019; online 22 February 2019)

In the crystal structure of the solvated pentacyclic title compound, C₂₁H₁₀Cl₄·0.5C₆H₁₂, the pentacyclic chloroaromatic rings are arranged in parallel layers, with the chlorine atoms protruding from these planes. Channels orthogonal to these layers are filled with disordered cyclohexane molecules.

Keywords: crystal structure; chlorine; polycyclic aromatics; disorder.

CCDC reference: 1897363

Structure description

The pentacyclic compound C₂₁H₂₀Cl₄ (Fig. 1) appeared as a new byproduct in the synthesis of the 13,13-dichloro analogue, an intermediate for bis-(dibenzo[a.i])fluorenylidene (Bergmann et al., 1953 , Franzen & Joschek, 1961 ), a biradical still under discussion (Kanawati et al., 2012 ; Wentrup et al., 2016 ). Eight identical molecules fill the unit cell, these aromatic compounds are essentially planar, the largest deviation from the mean plane being 0.0164 (18) Å at C8. With a bond angle of 107.26 (9)°, the Cl1—C1—Cl2 unit makes an angle of 89.97 (11)° to the aromatic plane. In the crystal, the molecules are arranged in layers parallel to the ac plane with an interlayer spacing of 3.28 Å. Channels along the b-axis direction (Fig. 2) are filled with one disordered cyclohexane molecule per two dibenzofluorene molecules.

Figure 1
Perspective view of the title compound. Displacement ellipsoids are drawn at the 50% probability level. Only one component of the disordered cyclohexane solvent molecule is shown.

Figure 2
Part of the packing diagram. View along the b axis.

Synthesis and crystallization

Bis-α-naphthylketone (10.0 g), prepared from α-cyanonaphthalene according to Blicke (1927 ), was added to PCl₅ (13.0 g) and the mixture was heated to 423 K for 5 h. Following the procedure of Magidson (1925 ), additional PCl₅ (13.0 g) was added, and after 5 h at 423 K, cooled to ambient temperature and the residue washed with light petroleum. The yield after threefold recrystallization from toluene solution was 0.6 g of a yellow solid with m.p. = 505–509 K. Single crystals were grown by slow evaporation of a solution in chloroform/cyclohexane (1/2). IR (KBr): 3420, 3072, 1620, 1566, 1518, 1421, 1376, 1344, 1288, 1261, 1195, 1161, 1072, 1029, 956, 930, 853, 795, 764, 728, 623, 584, 533, 519, 501, 429. ¹H NMR (400 MHz, CDCl₃): 8.77 (dd, 2H, 6-H), 8.41 (d, 2 H, 3-H), 7.91 (2, 2 H, 1-H), 7.80 (m, 2 H, 5-H), 7.69 (m, 2 H, 4-H).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1. The solvent molecule (cyclohexane) is highly disordered and was refined using split positions. The s.o.f. were kept fixed due to the imposed symmetry. The displacement parameters of the solvent atoms were restrained to approximate isotropic behaviour. Equivalent bond lengths and angles involving the disordered atoms were restrained to be equal.

Table 1
Experimental details

Crystal data
Chemical formula	C₂₁H₁₀Cl₄·0.5C₆H₁₂
M_r	446.17
Crystal system, space group	Monoclinic, I2/c
Temperature (K)	120
a, b, c (Å)	13.7822 (6), 10.7752 (4), 27.0787 (13)
β (°)	99.901 (4)
V (Å³)	3961.5 (3)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	0.61
Crystal size (mm)	0.90 × 0.37 × 0.08

Data collection
Diffractometer	Stoe IPDS 2T
Absorption correction	Integration (X-RED and X-AREA; Stoe & Cie, 1996 )
T_min, T_max	0.736, 0.952
No. of measured, independent and observed [I > 2σ(I)] reflections	11344, 4935, 4194
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.102, 1.05
No. of reflections	4935
No. of parameters	290
No. of restraints	66
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.51
Computer programs: X-RED and X-AREA (Stoe & Cie, 1996), SIR2004 (Altomare et al., 1999 ), SHELXL2018 (Sheldrick, 2015 ) and PLATON (Spek, 2009 ).

Structural data

CCDC reference: 1897363

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2414314619002360/bt4083sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314619002360/bt4083Isup2.hkl

checkCIF report

Computing details top

Data collection: X-RED and X-AREA (Stoe & Cie, 1996); cell refinement: X-RED and X-AREA (Stoe & Cie, 1996); data reduction: X-RED and X-AREA (Stoe & Cie, 1996); program(s) used to solve structure: SIR2004 (Altomare et al., 1999); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009).

5,8,13,13-Tetrachloro-13H-dibenzo[a,i]fluorene cyclohexane hemisolvate top

Crystal data top

C₂₁H₁₀Cl₄·0.5C₆H₁₂	F(000) = 1824
M_r = 446.17	D_x = 1.496 Mg m⁻³
Monoclinic, I2/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.7822 (6) Å	Cell parameters from 17812 reflections
b = 10.7752 (4) Å	θ = 2.0–28.6°
c = 27.0787 (13) Å	µ = 0.61 mm⁻¹
β = 99.901 (4)°	T = 120 K
V = 3961.5 (3) Å³	Plate, colourless
Z = 8	0.90 × 0.37 × 0.08 mm

Data collection top

Stoe IPDS 2T diffractometer	4935 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	4194 reflections with I > 2σ(I)
Detector resolution: 6.67 pixels mm^-1	R_int = 0.018
rotation method scans	θ_max = 28.4°, θ_min = 2.0°
Absorption correction: integration (X-RED and X-AREA; Stoe & Cie, 1996)	h = −18→18
T_min = 0.736, T_max = 0.952	k = −14→14
11344 measured reflections	l = −33→36

Refinement top

Refinement on F²	66 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.039	H-atom parameters constrained
wR(F²) = 0.102	w = 1/[σ²(F_o²) + (0.047P)² + 6.8104P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.002
4935 reflections	Δρ_max = 0.51 e Å⁻³
290 parameters	Δρ_min = −0.50 e Å⁻³

Special details top

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.

Refinement. Hydrogen atoms attached to carbons were placed at calculated positions and were refined in the riding-model approximation with isotropic displacement parameters.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cl1	0.74520 (3)	0.24458 (4)	0.60278 (2)	0.02905 (11)
Cl2	0.53125 (3)	0.23873 (4)	0.58942 (2)	0.02864 (11)
Cl3	0.63077 (3)	0.87411 (4)	0.59660 (2)	0.03174 (12)
Cl4	0.61148 (4)	0.43078 (5)	0.35395 (2)	0.03516 (13)
C1	0.63442 (12)	0.32199 (16)	0.57254 (6)	0.0221 (3)
C2	0.63383 (12)	0.45706 (16)	0.58782 (7)	0.0217 (3)
C3	0.63784 (13)	0.51050 (17)	0.63570 (7)	0.0244 (3)
C4	0.64182 (15)	0.44129 (19)	0.68067 (7)	0.0307 (4)
H4	0.642579	0.353188	0.679465	0.037*
C5	0.64455 (17)	0.4998 (2)	0.72553 (8)	0.0387 (5)
H5	0.646238	0.452034	0.755159	0.046*
C6	0.64488 (18)	0.6299 (2)	0.72840 (8)	0.0403 (5)
H6	0.647220	0.669447	0.759936	0.048*
C7	0.64187 (16)	0.6999 (2)	0.68613 (8)	0.0340 (4)
H7	0.642775	0.787869	0.688647	0.041*
C8	0.63741 (13)	0.64337 (17)	0.63870 (7)	0.0254 (4)
C9	0.63181 (12)	0.71300 (17)	0.59358 (7)	0.0247 (4)
C10	0.62704 (12)	0.65911 (17)	0.54760 (7)	0.0242 (3)
H10	0.622833	0.708019	0.518124	0.029*
C11	0.62854 (12)	0.52906 (16)	0.54535 (6)	0.0215 (3)
C12	0.62551 (12)	0.44863 (16)	0.50131 (7)	0.0221 (3)
C13	0.62051 (12)	0.48153 (17)	0.45073 (7)	0.0248 (4)
H13	0.618390	0.566095	0.440677	0.030*
C14	0.61879 (12)	0.38833 (19)	0.41650 (7)	0.0257 (4)
C15	0.62220 (12)	0.26011 (18)	0.42978 (7)	0.0249 (4)
C16	0.62121 (13)	0.1634 (2)	0.39421 (7)	0.0294 (4)
H16	0.618368	0.183259	0.359817	0.035*
C17	0.62430 (14)	0.0420 (2)	0.40878 (8)	0.0331 (4)
H17	0.623363	−0.021715	0.384455	0.040*
C18	0.62885 (14)	0.01062 (19)	0.45940 (8)	0.0315 (4)
H18	0.631065	−0.074267	0.469000	0.038*
C19	0.63012 (13)	0.10069 (17)	0.49512 (7)	0.0272 (4)
H19	0.632970	0.077843	0.529224	0.033*
C20	0.62723 (12)	0.22794 (17)	0.48156 (7)	0.0237 (3)
C21	0.62889 (12)	0.32607 (16)	0.51631 (6)	0.0224 (3)
C1L	0.500000	−0.0571 (8)	0.750000	0.053 (2)	0.5
H1L1	0.530101	−0.111210	0.778039	0.063*	0.25
H1L2	0.469897	−0.111206	0.721960	0.063*	0.25
C2L	0.5837 (6)	0.0253 (8)	0.7298 (4)	0.098 (3)	0.5
H2L1	0.646442	−0.021233	0.733130	0.117*	0.5
H2L2	0.562314	0.047455	0.694063	0.117*	0.5
C3L	0.5967 (4)	0.1440 (5)	0.7630 (2)	0.0488 (11)	0.5
H3L1	0.609680	0.121636	0.798953	0.059*	0.5
H3L2	0.652236	0.194808	0.755464	0.059*	0.5
C4L	0.500000	0.2150 (7)	0.750000	0.0497 (19)	0.5
H4L1	0.493161	0.269490	0.778629	0.060*	0.25
H4L2	0.506841	0.269488	0.721371	0.060*	0.25
C1M	0.4912 (6)	−0.0506 (8)	0.7717 (3)	0.0326 (17)	0.25
H1M1	0.492958	−0.136370	0.757813	0.039*	0.25
H1M2	0.479821	−0.055842	0.806770	0.039*	0.25
C2M	0.5902 (3)	0.0093 (4)	0.76390 (19)	0.0419 (10)	0.5
H2M1	0.620698	0.029383	0.798809	0.050*	0.5
H2M2	0.634240	−0.049693	0.750461	0.050*	0.5
C3M	0.5827 (7)	0.1294 (8)	0.7328 (4)	0.094 (2)	0.5
H3M1	0.595833	0.107738	0.698994	0.112*	0.5
H3M2	0.635843	0.186338	0.748122	0.112*	0.5
C4M	0.4818 (7)	0.2036 (8)	0.7269 (4)	0.0376 (19)	0.25
H4M1	0.447575	0.199768	0.691691	0.045*	0.25
H4M2	0.493363	0.291640	0.736596	0.045*	0.25

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0292 (2)	0.0266 (2)	0.0289 (2)	0.00530 (16)	−0.00196 (17)	0.00312 (17)
Cl2	0.0305 (2)	0.0274 (2)	0.0290 (2)	−0.00694 (16)	0.00791 (17)	0.00400 (17)
Cl3	0.0293 (2)	0.0222 (2)	0.0446 (3)	−0.00073 (16)	0.00885 (19)	0.00088 (18)
Cl4	0.0333 (2)	0.0510 (3)	0.0216 (2)	−0.0015 (2)	0.00606 (17)	0.0058 (2)
C1	0.0207 (8)	0.0226 (8)	0.0227 (8)	−0.0010 (6)	0.0029 (6)	0.0036 (6)
C2	0.0179 (7)	0.0224 (8)	0.0246 (8)	−0.0006 (6)	0.0036 (6)	0.0016 (6)
C3	0.0215 (8)	0.0261 (8)	0.0255 (8)	−0.0015 (6)	0.0038 (6)	0.0025 (7)
C4	0.0364 (10)	0.0289 (9)	0.0268 (9)	−0.0042 (8)	0.0058 (8)	0.0025 (7)
C5	0.0519 (13)	0.0398 (11)	0.0250 (9)	−0.0052 (10)	0.0086 (9)	0.0034 (9)
C6	0.0541 (13)	0.0402 (12)	0.0275 (10)	−0.0079 (10)	0.0098 (9)	−0.0065 (9)
C7	0.0385 (11)	0.0307 (10)	0.0333 (10)	−0.0060 (8)	0.0080 (8)	−0.0051 (8)
C8	0.0215 (8)	0.0261 (8)	0.0290 (9)	−0.0025 (7)	0.0052 (7)	−0.0006 (7)
C9	0.0178 (7)	0.0223 (8)	0.0343 (9)	−0.0009 (6)	0.0051 (7)	0.0010 (7)
C10	0.0182 (8)	0.0254 (8)	0.0294 (9)	−0.0007 (6)	0.0049 (7)	0.0067 (7)
C11	0.0157 (7)	0.0244 (8)	0.0246 (8)	0.0002 (6)	0.0036 (6)	0.0033 (6)
C12	0.0164 (7)	0.0258 (8)	0.0240 (8)	−0.0004 (6)	0.0031 (6)	0.0034 (7)
C13	0.0189 (8)	0.0286 (9)	0.0272 (9)	−0.0004 (6)	0.0048 (6)	0.0071 (7)
C14	0.0177 (8)	0.0391 (10)	0.0203 (8)	−0.0003 (7)	0.0035 (6)	0.0042 (7)
C15	0.0163 (7)	0.0335 (9)	0.0246 (8)	−0.0004 (6)	0.0029 (6)	−0.0005 (7)
C16	0.0206 (8)	0.0415 (11)	0.0255 (9)	−0.0002 (7)	0.0029 (7)	−0.0059 (8)
C17	0.0229 (9)	0.0390 (11)	0.0364 (10)	−0.0001 (8)	0.0017 (8)	−0.0123 (9)
C18	0.0248 (9)	0.0283 (9)	0.0399 (11)	−0.0002 (7)	0.0012 (8)	−0.0045 (8)
C19	0.0235 (8)	0.0271 (9)	0.0300 (9)	−0.0005 (7)	0.0018 (7)	0.0002 (7)
C20	0.0168 (7)	0.0281 (8)	0.0257 (8)	−0.0001 (6)	0.0019 (6)	0.0001 (7)
C21	0.0180 (7)	0.0253 (8)	0.0236 (8)	0.0005 (6)	0.0030 (6)	0.0033 (7)
C1L	0.055 (3)	0.049 (3)	0.055 (3)	0.000	0.0094 (19)	0.000
C2L	0.096 (3)	0.096 (3)	0.101 (3)	0.0071 (19)	0.0155 (19)	−0.0107 (19)
C3L	0.0497 (18)	0.0403 (17)	0.0541 (19)	−0.0057 (15)	0.0023 (15)	0.0018 (15)
C4L	0.051 (2)	0.046 (2)	0.052 (2)	0.000	0.0086 (18)	0.000
C1M	0.034 (2)	0.032 (2)	0.032 (2)	−0.0033 (17)	0.0066 (18)	0.0050 (18)
C2M	0.0451 (17)	0.0398 (17)	0.0400 (17)	−0.0001 (14)	0.0049 (14)	0.0038 (14)
C3M	0.094 (3)	0.092 (3)	0.097 (3)	0.0002 (19)	0.0210 (19)	0.0097 (19)
C4M	0.042 (2)	0.035 (2)	0.037 (3)	−0.0017 (18)	0.0076 (18)	0.0019 (19)

Geometric parameters (Å, º) top

Cl1—C1	1.8077 (17)	C17—H17	0.9500
Cl2—C1	1.8052 (17)	C18—C19	1.368 (3)
Cl3—C9	1.7380 (19)	C18—H18	0.9500
Cl4—C14	1.7407 (18)	C19—C20	1.418 (3)
C1—C21	1.512 (2)	C19—H19	0.9500
C1—C2	1.513 (2)	C20—C21	1.413 (3)
C2—C11	1.379 (2)	C1L—C2Lⁱ	1.624 (9)
C2—C3	1.411 (2)	C1L—C2L	1.624 (9)
C3—C4	1.421 (3)	C1L—H1L1	0.9900
C3—C8	1.434 (3)	C1L—H1L2	0.9900
C4—C5	1.363 (3)	C2L—C3L	1.556 (8)
C4—H4	0.9500	C2L—H2L1	0.9900
C5—C6	1.404 (3)	C2L—H2L2	0.9900
C5—H5	0.9500	C3L—C4L	1.524 (6)
C6—C7	1.366 (3)	C3L—H3L1	0.9900
C6—H6	0.9500	C3L—H3L2	0.9900
C7—C8	1.414 (3)	C4L—H4L1	0.9900
C7—H7	0.9500	C4L—H4L2	0.9900
C8—C9	1.424 (3)	C1M—C1Mⁱ	1.241 (18)
C9—C10	1.365 (3)	C1M—C2Mⁱ	1.495 (10)
C10—C11	1.403 (2)	C1M—C2M	1.556 (8)
C10—H10	0.9500	C1M—H1M1	1.0003
C11—C12	1.469 (2)	C1M—H1M2	0.9900
C12—C21	1.380 (2)	C2M—C3M	1.539 (8)
C12—C13	1.405 (2)	C2M—H2M1	0.9900
C13—C14	1.364 (3)	C2M—H2M2	0.9900
C13—H13	0.9500	C3M—C4M	1.588 (10)
C14—C15	1.426 (3)	C3M—C4Mⁱ	1.719 (13)
C15—C16	1.418 (3)	C3M—H3M1	0.9900
C15—C20	1.435 (2)	C3M—H3M2	0.9900
C16—C17	1.364 (3)	C4M—C4Mⁱ	1.264 (19)
C16—H16	0.9500	C4M—H4M1	0.9900
C17—C18	1.403 (3)	C4M—H4M2	0.9900

C21—C1—C2	104.22 (14)	C20—C21—C1	129.87 (16)
C21—C1—Cl2	111.34 (12)	C2Lⁱ—C1L—C2L	113.7 (7)
C2—C1—Cl2	111.54 (12)	C2Lⁱ—C1L—H1L1	107.0
C21—C1—Cl1	111.22 (12)	C2L—C1L—H1L1	110.6
C2—C1—Cl1	111.32 (12)	C2Lⁱ—C1L—H1L2	110.6
Cl2—C1—Cl1	107.26 (9)	C2L—C1L—H1L2	106.9
C11—C2—C3	121.66 (16)	H1L1—C1L—H1L2	107.9
C11—C2—C1	108.36 (15)	C3L—C2L—C1L	105.8 (6)
C3—C2—C1	129.98 (16)	C3L—C2L—H2L1	110.6
C2—C3—C4	124.26 (17)	C1L—C2L—H2L1	110.6
C2—C3—C8	117.35 (16)	C3L—C2L—H2L2	110.6
C4—C3—C8	118.39 (17)	C1L—C2L—H2L2	110.6
C5—C4—C3	120.80 (19)	H2L1—C2L—H2L2	108.7
C5—C4—H4	119.6	C4L—C3L—C2L	105.7 (5)
C3—C4—H4	119.6	C4L—C3L—H3L1	110.6
C4—C5—C6	120.7 (2)	C2L—C3L—H3L1	110.6
C4—C5—H5	119.7	C4L—C3L—H3L2	110.6
C6—C5—H5	119.7	C2L—C3L—H3L2	110.6
C7—C6—C5	120.4 (2)	H3L1—C3L—H3L2	108.7
C7—C6—H6	119.8	C3L—C4L—C3Lⁱ	119.8 (6)
C5—C6—H6	119.8	C3L—C4L—H4L1	108.3
C6—C7—C8	120.9 (2)	C3Lⁱ—C4L—H4L1	106.3
C6—C7—H7	119.5	C3L—C4L—H4L2	106.3
C8—C7—H7	119.5	C3Lⁱ—C4L—H4L2	108.3
C7—C8—C9	122.67 (18)	H4L1—C4L—H4L2	107.2
C7—C8—C3	118.80 (17)	C1Mⁱ—C1M—C2M	63.4 (6)
C9—C8—C3	118.53 (17)	C2Mⁱ—C1M—C2M	108.2 (6)
C10—C9—C8	123.03 (17)	C1Mⁱ—C1M—H1M1	67.8
C10—C9—Cl3	117.92 (14)	C2Mⁱ—C1M—H1M1	102.7
C8—C9—Cl3	119.05 (14)	C2M—C1M—H1M1	104.7
C9—C10—C11	117.76 (17)	C1Mⁱ—C1M—H1M2	176.1
C9—C10—H10	121.1	C2Mⁱ—C1M—H1M2	114.7
C11—C10—H10	121.1	C2M—C1M—H1M2	116.2
C2—C11—C10	121.66 (17)	H1M1—C1M—H1M2	109.0
C2—C11—C12	109.59 (15)	H1L1ⁱ—C1M—H1L2ⁱ	82.1
C10—C11—C12	128.75 (16)	C1Mⁱ—C2M—C3M	92.1 (6)
C21—C12—C13	121.45 (17)	C1Mⁱ—C2M—C1M	47.9 (7)
C21—C12—C11	109.32 (15)	C3M—C2M—C1M	116.4 (5)
C13—C12—C11	129.22 (16)	C1Mⁱ—C2M—H2M1	149.1
C14—C13—C12	117.96 (17)	C3M—C2M—H2M1	108.5
C14—C13—H13	121.0	C1M—C2M—H2M1	101.4
C12—C13—H13	121.0	C1Mⁱ—C2M—H2M2	85.7
C13—C14—C15	123.09 (16)	C3M—C2M—H2M2	109.1
C13—C14—Cl4	117.32 (15)	C1M—C2M—H2M2	113.0
C15—C14—Cl4	119.58 (14)	H2M1—C2M—H2M2	107.8
C16—C15—C14	123.03 (17)	C2M—C3M—C4M	116.9 (7)
C16—C15—C20	118.65 (17)	C2M—C3M—C4Mⁱ	92.1 (6)
C14—C15—C20	118.31 (16)	C4M—C3M—C4Mⁱ	44.7 (7)
C17—C16—C15	120.81 (18)	C2M—C3M—H3M1	107.6
C17—C16—H16	119.6	C4M—C3M—H3M1	108.8
C15—C16—H16	119.6	C4Mⁱ—C3M—H3M1	153.2
C16—C17—C18	120.50 (18)	C2M—C3M—H3M2	108.4
C16—C17—H17	119.8	C4M—C3M—H3M2	107.6
C18—C17—H17	119.8	C4Mⁱ—C3M—H3M2	82.6
C19—C18—C17	120.85 (19)	H3M1—C3M—H3M2	107.2
C19—C18—H18	119.6	C4Mⁱ—C4M—C3M	73.1 (8)
C17—C18—H18	119.6	C4Mⁱ—C4M—H4M1	174.5
C18—C19—C20	120.42 (18)	C3M—C4M—H4M1	109.8
C18—C19—H19	119.8	C3Mⁱ—C4M—H4M1	112.3
C20—C19—H19	119.8	C4Mⁱ—C4M—H4M2	73.8
C21—C20—C19	123.69 (17)	C3M—C4M—H4M2	110.9
C21—C20—C15	117.56 (16)	C3Mⁱ—C4M—H4M2	110.8
C19—C20—C15	118.76 (17)	H4M1—C4M—H4M2	108.8
C12—C21—C20	121.63 (16)	H4L1ⁱ—C4M—H4L2ⁱ	77.7
C12—C21—C1	108.50 (15)

C21—C1—C2—C11	0.04 (18)	Cl4—C14—C15—C16	0.8 (2)
Cl2—C1—C2—C11	−120.21 (13)	C13—C14—C15—C20	0.3 (3)
Cl1—C1—C2—C11	120.02 (13)	Cl4—C14—C15—C20	−179.39 (12)
C21—C1—C2—C3	−179.87 (17)	C14—C15—C16—C17	−179.80 (17)
Cl2—C1—C2—C3	59.9 (2)	C20—C15—C16—C17	0.4 (3)
Cl1—C1—C2—C3	−59.9 (2)	C15—C16—C17—C18	−0.2 (3)
C11—C2—C3—C4	178.98 (17)	C16—C17—C18—C19	0.1 (3)
C1—C2—C3—C4	−1.1 (3)	C17—C18—C19—C20	−0.2 (3)
C11—C2—C3—C8	−0.7 (2)	C18—C19—C20—C21	−179.61 (17)
C1—C2—C3—C8	179.16 (16)	C18—C19—C20—C15	0.5 (3)
C2—C3—C4—C5	−179.32 (19)	C16—C15—C20—C21	179.52 (15)
C8—C3—C4—C5	0.4 (3)	C14—C15—C20—C21	−0.3 (2)
C3—C4—C5—C6	−0.9 (3)	C16—C15—C20—C19	−0.6 (2)
C4—C5—C6—C7	0.4 (4)	C14—C15—C20—C19	179.67 (16)
C5—C6—C7—C8	0.6 (4)	C13—C12—C21—C20	−0.2 (3)
C6—C7—C8—C9	178.47 (19)	C11—C12—C21—C20	−179.88 (15)
C6—C7—C8—C3	−1.1 (3)	C13—C12—C21—C1	179.72 (15)
C2—C3—C8—C7	−179.68 (16)	C11—C12—C21—C1	0.01 (19)
C4—C3—C8—C7	0.6 (3)	C19—C20—C21—C12	−179.72 (16)
C2—C3—C8—C9	0.7 (2)	C15—C20—C21—C12	0.2 (2)
C4—C3—C8—C9	−178.99 (16)	C19—C20—C21—C1	0.4 (3)
C7—C8—C9—C10	−179.69 (17)	C15—C20—C21—C1	−179.66 (16)
C3—C8—C9—C10	−0.1 (3)	C2—C1—C21—C12	−0.03 (18)
C7—C8—C9—Cl3	0.2 (2)	Cl2—C1—C21—C12	120.35 (13)
C3—C8—C9—Cl3	179.77 (13)	Cl1—C1—C21—C12	−120.08 (13)
C8—C9—C10—C11	−0.5 (3)	C2—C1—C21—C20	179.85 (17)
Cl3—C9—C10—C11	179.60 (12)	Cl2—C1—C21—C20	−59.8 (2)
C3—C2—C11—C10	0.1 (3)	Cl1—C1—C21—C20	59.8 (2)
C1—C2—C11—C10	−179.81 (15)	C2Lⁱ—C1L—C2L—C3L	33.3 (4)
C3—C2—C11—C12	179.88 (15)	C1L—C2L—C3L—C4L	−66.8 (7)
C1—C2—C11—C12	−0.03 (19)	C2L—C3L—C4L—C3Lⁱ	34.5 (4)
C9—C10—C11—C2	0.5 (3)	C2Mⁱ—C1M—C2M—C1Mⁱ	−53.6 (7)
C9—C10—C11—C12	−179.21 (16)	C1Mⁱ—C1M—C2M—C3M	66.9 (6)
C2—C11—C12—C21	0.02 (19)	C2Mⁱ—C1M—C2M—C3M	13.3 (9)
C10—C11—C12—C21	179.78 (16)	C1Mⁱ—C2M—C3M—C4M	62.5 (9)
C2—C11—C12—C13	−179.67 (16)	C1M—C2M—C3M—C4M	19.4 (11)
C10—C11—C12—C13	0.1 (3)	C1Mⁱ—C2M—C3M—C4Mⁱ	101.3 (6)
C21—C12—C13—C14	0.2 (2)	C1M—C2M—C3M—C4Mⁱ	58.2 (8)
C11—C12—C13—C14	179.83 (16)	C2M—C3M—C4M—C4Mⁱ	62.9 (8)
C12—C13—C14—C15	−0.2 (3)	C2M—C3M—C4M—C3Mⁱ	8.3 (10)
C12—C13—C14—Cl4	179.44 (12)	C4Mⁱ—C3M—C4M—C3Mⁱ	−54.6 (6)
C13—C14—C15—C16	−179.47 (17)

Symmetry code: (i) −x+1, y, −z+3/2.

Acknowledgements

The authors are grateful to M. Prenzel for the synthesis of this compound.

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