5,10-Di­hydro­indeno­[2,1-a]indene

Detert, H.; Schollmeyer, D.

doi:10.1107/S2414314619011799

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 4| Part 8| August 2019| x191179

https://doi.org/10.1107/S2414314619011799

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5,10-Dihydroindeno[2,1-a]indene

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 26 August 2019; accepted 27 August 2019; online 30 August 2019)

The title compound, C₁₆H₁₂, crystallizes with four half molecules in the asymmetric unit, each of which is located on a crystallographic centre of inversion. The molecules are essentially planar. The crystal studied was a non-merohedral twin.

Keywords: crystal structure; polycyclic hydrocarbon; planarized stilbene.

CCDC reference: 1949606

Structure description

Indenoindene is well known as starting material for e.g. pentalenes (Frank & Gompper, 1987 ) and has been studied as a stiffened stilbene (Ogawa et al., 1988 ; Krohn et al., 2019 ). While the compound is formed in pyrolytic processes (Hofmann et al., 1995 ), synthetic routes involve benzocyclobutene derivatives (Barton & Shepherd 1987 ; Schiess & Heitzmann 1977 ; Detert & Schollmeyer 2018 ) and a photochemical rearrangement (Oelgemöller et al., 2002 ).

Four independent and nearly identical molecules of the title compound with essential C_2h symmetry fill the unit cell (Fig. 1). The crystal packing shows pairs of tilted molecules along the a axis and along the b axis (Fig. 2). The molecules are completely planar [maximum deviation from the mean plane of all carbon atoms in a molecule: 0.014 (3) Å for C6D]. The central dihydropentalene unit shows averaged bond lengths of 1.466 (4) Å for C2—C3 and 1.331 (4) Å for C2—C2′. A comparison of these data with trans stilbene (1.466 and 1.324 Å, respectively; Luo et al., 2019 ) reveals a bond-length convergence in the planarized indenoindene [dihedral angle = 1.2 (2)°] relative to the twisted stilbene (phenylethenyl torsion angle = 6.64°)

Figure 1
Perspective view of the title compound. Displacement ellipsoids are drawn at the 50% probability level.

Figure 2
Packing diagram of the title compound viewed along the a axis. Symmetry-independent molecules are drawn with different colours.

Synthesis and crystallization

The title compound was prepared according to Oelgemöller et al. (2002). Single crystals were obtained by slow evaporation of a solution in dichloromethane/propanol-2 (2:1).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1. The crystal studied was a non-merohedral two-component twin with a fractional contribution of 0.4085 (12) for the minor domain.

Table 1
Experimental details

Crystal data
Chemical formula	C₁₆H₁₂
M_r	204.26
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	193
a, b, c (Å)	7.5009 (9), 7.6819 (9), 19.387 (3)
α, β, γ (°)	99.733 (11), 100.641 (11), 90.523 (9)
V (Å³)	1081.2 (2)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.07
Crystal size (mm)	0.22 × 0.15 × 0.04

Data collection
Diffractometer	Stoe IPDS 2T
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	14443, 14443, 7500
R_int	?
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.141, 1.03
No. of reflections	14443
No. of parameters	290
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.21
Computer programs: X-AREA and X-RED (Stoe & Cie, 1996 ), SHELXT2014 (Sheldrick, 2015a ), SHELXL2018 (Sheldrick, 2015b ) and PLATON (Spek, 2009 ).

Structural data

CCDC reference: 1949606

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2414314619011799/bt4085sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314619011799/bt4085Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314619011799/bt4085Isup3.cml

checkCIF report

Computing details top

Data collection: X-AREA (Stoe & Cie, 1996); cell refinement: X-AREA (Stoe & Cie, 1996); data reduction: X-RED (Stoe & Cie, 1996); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2018 (Sheldrick, 2015b).

5,10-Dihydroindeno[2,1-a]indene top

Crystal data top

C₁₆H₁₂	Z = 4
M_r = 204.26	F(000) = 432
Triclinic, P1	D_x = 1.255 Mg m⁻³
a = 7.5009 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.6819 (9) Å	Cell parameters from 2411 reflections
c = 19.387 (3) Å	θ = 2.8–28.0°
α = 99.733 (11)°	µ = 0.07 mm⁻¹
β = 100.641 (11)°	T = 193 K
γ = 90.523 (9)°	Plate, colourless
V = 1081.2 (2) Å³	0.22 × 0.15 × 0.04 mm

Data collection top

Stoe IPDS 2T diffractometer	7500 reflections with I > 2σ(I)
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	θ_max = 28.4°, θ_min = 2.7°
Detector resolution: 6.67 pixels mm^-1	h = −9→9
rotation method scans	k = −10→10
14443 measured reflections	l = −25→25
14443 independent reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.056	H-atom parameters constrained
wR(F²) = 0.141	w = 1/[σ²(F_o²) + (0.0513P)² + 0.1143P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
14443 reflections	Δρ_max = 0.29 e Å⁻³
290 parameters	Δρ_min = −0.21 e Å⁻³
0 restraints

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. Refined as a 2-component twin. BASF 0.40850 Twin law for transforming hkl(1) to hkl(2): -1.00006 0.00023 0.00003 0.00016 -1.00020 0.00001 0.95946 0.87001 1.00038

Hydrogen atoms attached to carbons were placed at calculated positions and were refined in the riding-model approximation with isotropic displacement parameters set to 1.2 U_eq(C).

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

	x	y	z	U_iso*/U_eq
C1A	0.6265 (4)	0.1349 (3)	0.58366 (16)	0.0420 (7)
H1A	0.570270	0.239199	0.607100	0.050*
H1B	0.758394	0.160278	0.588948	0.050*
C2A	0.5377 (3)	0.0821 (3)	0.50682 (15)	0.0379 (7)
C3A	0.5094 (3)	0.1575 (3)	0.44194 (16)	0.0371 (7)
C4A	0.5622 (3)	0.3197 (3)	0.42737 (17)	0.0424 (7)
H4A	0.627703	0.406985	0.464147	0.051*
C5A	0.5171 (4)	0.3509 (4)	0.35798 (18)	0.0463 (8)
H5A	0.553328	0.460341	0.347082	0.056*
C6A	0.4206 (4)	0.2254 (4)	0.30472 (18)	0.0475 (8)
H6A	0.390593	0.250000	0.257642	0.057*
C7A	0.3663 (4)	0.0633 (4)	0.31857 (17)	0.0461 (8)
H7A	0.299603	−0.022537	0.281531	0.055*
C8A	0.4111 (3)	0.0299 (3)	0.38696 (16)	0.0396 (7)
C1B	0.9607 (4)	0.6291 (3)	0.58564 (17)	0.0485 (8)
H1C	0.834972	0.652170	0.592501	0.058*
H1D	1.040849	0.733646	0.609137	0.058*
C2B	0.9702 (4)	0.5806 (3)	0.50825 (17)	0.0428 (7)
C3B	0.9306 (3)	0.6610 (3)	0.44363 (17)	0.0416 (7)
C4B	0.8648 (4)	0.8222 (3)	0.43136 (18)	0.0472 (8)
H4B	0.837765	0.907055	0.469307	0.057*
C5B	0.8391 (4)	0.8579 (4)	0.36300 (19)	0.0512 (8)
H5B	0.792298	0.967956	0.353938	0.061*
C6B	0.8799 (4)	0.7372 (4)	0.30744 (19)	0.0523 (8)
H6B	0.862114	0.765677	0.260901	0.063*
C7B	0.9472 (4)	0.5735 (4)	0.3191 (2)	0.0537 (9)
H7B	0.974921	0.489898	0.280873	0.064*
C8B	0.9724 (3)	0.5359 (3)	0.38743 (18)	0.0439 (7)
C1C	0.6484 (4)	0.4528 (4)	0.08155 (17)	0.0491 (8)
H1E	0.760177	0.527069	0.102405	0.059*
H1F	0.670975	0.328768	0.087230	0.059*
C2C	0.5827 (3)	0.4677 (3)	0.00581 (17)	0.0422 (7)
C3C	0.6498 (4)	0.4309 (3)	−0.06130 (17)	0.0422 (7)
C4C	0.8104 (4)	0.3624 (3)	−0.07899 (18)	0.0506 (8)
H4C	0.903217	0.330126	−0.043541	0.061*
C5C	0.8316 (4)	0.3425 (3)	−0.14959 (19)	0.0530 (8)
H5C	0.939557	0.295384	−0.162728	0.064*
C6C	0.6969 (4)	0.3906 (4)	−0.20061 (19)	0.0537 (8)
H6C	0.713696	0.377195	−0.248581	0.064*
C7C	0.5370 (4)	0.4585 (4)	−0.18306 (19)	0.0512 (8)
H7C	0.445029	0.491165	−0.218706	0.061*
C8C	0.5134 (4)	0.4776 (3)	−0.11433 (17)	0.0429 (7)
C1D	0.1447 (4)	0.1273 (4)	0.08064 (18)	0.0545 (8)
H1G	0.168542	0.255730	0.083898	0.065*
H1H	0.255170	0.074407	0.103547	0.065*
C2D	0.0818 (4)	0.0383 (3)	0.00570 (18)	0.0461 (8)
C3D	0.1529 (4)	0.0084 (3)	−0.06117 (18)	0.0451 (7)
C4D	0.3153 (4)	0.0594 (3)	−0.07869 (19)	0.0525 (8)
H4D	0.406367	0.127811	−0.043834	0.063*
C5D	0.3409 (4)	0.0080 (4)	−0.1484 (2)	0.0555 (8)
H5D	0.450338	0.041999	−0.161536	0.067*
C6D	0.2082 (5)	−0.0922 (4)	−0.1985 (2)	0.0569 (9)
H6D	0.227975	−0.128483	−0.245749	0.068*
C7D	0.0464 (4)	−0.1404 (4)	−0.18077 (19)	0.0538 (8)
H7D	−0.044961	−0.208078	−0.215738	0.065*
C8D	0.0193 (4)	−0.0903 (3)	−0.11304 (19)	0.0467 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1A	0.0377 (15)	0.0378 (14)	0.0459 (19)	−0.0018 (11)	0.0034 (13)	−0.0003 (12)
C2A	0.0280 (14)	0.0375 (14)	0.046 (2)	0.0033 (11)	0.0065 (13)	0.0017 (13)
C3A	0.0260 (13)	0.0400 (14)	0.045 (2)	0.0029 (10)	0.0086 (13)	0.0063 (13)
C4A	0.0326 (14)	0.0404 (15)	0.052 (2)	−0.0012 (11)	0.0064 (14)	0.0024 (14)
C5A	0.0391 (16)	0.0437 (16)	0.059 (2)	0.0007 (12)	0.0120 (15)	0.0131 (15)
C6A	0.0438 (17)	0.0529 (17)	0.046 (2)	0.0044 (13)	0.0081 (15)	0.0107 (15)
C7A	0.0433 (17)	0.0443 (16)	0.047 (2)	0.0017 (12)	0.0047 (15)	0.0003 (14)
C8A	0.0309 (14)	0.0378 (14)	0.050 (2)	0.0030 (11)	0.0107 (14)	0.0028 (13)
C1B	0.0444 (17)	0.0417 (15)	0.058 (2)	0.0015 (12)	0.0159 (15)	−0.0037 (13)
C2B	0.0300 (13)	0.0409 (14)	0.055 (2)	−0.0026 (10)	0.0113 (13)	−0.0038 (14)
C3B	0.0285 (14)	0.0421 (15)	0.054 (2)	−0.0032 (11)	0.0119 (14)	0.0043 (14)
C4B	0.0367 (15)	0.0449 (16)	0.060 (2)	0.0036 (12)	0.0139 (15)	0.0048 (15)
C5B	0.0392 (16)	0.0478 (17)	0.068 (3)	0.0023 (12)	0.0127 (16)	0.0111 (16)
C6B	0.0483 (18)	0.0549 (18)	0.055 (2)	−0.0045 (14)	0.0114 (16)	0.0123 (16)
C7B	0.0486 (18)	0.0484 (18)	0.062 (3)	−0.0057 (14)	0.0153 (17)	−0.0023 (16)
C8B	0.0325 (14)	0.0396 (15)	0.058 (2)	−0.0045 (11)	0.0101 (14)	0.0017 (14)
C1C	0.0473 (17)	0.0473 (16)	0.051 (2)	0.0010 (13)	−0.0026 (15)	0.0165 (14)
C2C	0.0426 (15)	0.0292 (13)	0.051 (2)	−0.0031 (11)	−0.0029 (15)	0.0103 (13)
C3C	0.0506 (17)	0.0307 (14)	0.046 (2)	−0.0035 (12)	0.0108 (15)	0.0083 (13)
C4C	0.0574 (19)	0.0395 (15)	0.055 (2)	0.0042 (13)	0.0067 (17)	0.0138 (15)
C5C	0.057 (2)	0.0428 (16)	0.060 (2)	0.0033 (13)	0.0187 (18)	0.0043 (15)
C6C	0.066 (2)	0.0473 (17)	0.048 (2)	−0.0080 (15)	0.0156 (18)	0.0038 (15)
C7C	0.0547 (19)	0.0494 (17)	0.047 (2)	−0.0093 (14)	0.0039 (16)	0.0083 (15)
C8C	0.0464 (17)	0.0334 (14)	0.047 (2)	−0.0053 (12)	0.0060 (15)	0.0067 (13)
C1D	0.0495 (18)	0.0459 (16)	0.062 (2)	−0.0013 (13)	−0.0032 (16)	0.0057 (15)
C2D	0.0440 (16)	0.0286 (14)	0.059 (2)	0.0023 (11)	−0.0074 (16)	0.0065 (14)
C3D	0.0525 (18)	0.0321 (14)	0.053 (2)	0.0110 (12)	0.0115 (16)	0.0130 (13)
C4D	0.0554 (19)	0.0352 (15)	0.063 (3)	−0.0011 (13)	0.0002 (17)	0.0086 (15)
C5D	0.055 (2)	0.0489 (17)	0.069 (3)	0.0053 (14)	0.0181 (18)	0.0218 (17)
C6D	0.068 (2)	0.0544 (18)	0.051 (2)	0.0175 (16)	0.0114 (19)	0.0142 (16)
C7D	0.0508 (19)	0.0484 (17)	0.058 (2)	0.0094 (14)	−0.0006 (17)	0.0090 (16)
C8D	0.0456 (17)	0.0354 (15)	0.058 (2)	0.0071 (12)	0.0029 (16)	0.0117 (14)

Geometric parameters (Å, º) top

C1A—C2A	1.500 (4)	C1C—C2C	1.484 (4)
C1A—C8Aⁱ	1.518 (4)	C1C—C8Cⁱⁱⁱ	1.531 (4)
C1A—H1A	0.9900	C1C—H1E	0.9900
C1A—H1B	0.9900	C1C—H1F	0.9900
C2A—C2Aⁱ	1.341 (4)	C2C—C2Cⁱⁱⁱ	1.335 (5)
C2A—C3A	1.453 (4)	C2C—C3C	1.465 (4)
C3A—C4A	1.393 (3)	C3C—C4C	1.396 (4)
C3A—C8A	1.408 (4)	C3C—C8C	1.406 (4)
C4A—C5A	1.387 (4)	C4C—C5C	1.390 (4)
C4A—H4A	0.9500	C4C—H4C	0.9500
C5A—C6A	1.376 (4)	C5C—C6C	1.377 (4)
C5A—H5A	0.9500	C5C—H5C	0.9500
C6A—C7A	1.390 (4)	C6C—C7C	1.388 (4)
C6A—H6A	0.9500	C6C—H6C	0.9500
C7A—C8A	1.374 (4)	C7C—C8C	1.360 (4)
C7A—H7A	0.9500	C7C—H7C	0.9500
C1B—C2B	1.499 (4)	C1D—C2D	1.485 (4)
C1B—C8Bⁱⁱ	1.506 (4)	C1D—C8D^iv	1.526 (4)
C1B—H1C	0.9900	C1D—H1G	0.9900
C1B—H1D	0.9900	C1D—H1H	0.9900
C2B—C2Bⁱⁱ	1.329 (5)	C2D—C2D^iv	1.321 (5)
C2B—C3B	1.472 (4)	C2D—C3D	1.475 (4)
C3B—C4B	1.379 (4)	C3D—C4D	1.393 (4)
C3B—C8B	1.410 (4)	C3D—C8D	1.395 (4)
C4B—C5B	1.378 (4)	C4D—C5D	1.392 (4)
C4B—H4B	0.9500	C4D—H4D	0.9500
C5B—C6B	1.379 (4)	C5D—C6D	1.380 (4)
C5B—H5B	0.9500	C5D—H5D	0.9500
C6B—C7B	1.397 (4)	C6D—C7D	1.385 (4)
C6B—H6B	0.9500	C6D—H6D	0.9500
C7B—C8B	1.384 (4)	C7D—C8D	1.357 (4)
C7B—H7B	0.9500	C7D—H7D	0.9500

C2A—C1A—C8Aⁱ	101.2 (2)	C2C—C1C—C8Cⁱⁱⁱ	100.7 (2)
C2A—C1A—H1A	111.5	C2C—C1C—H1E	111.6
C8Aⁱ—C1A—H1A	111.5	C8Cⁱⁱⁱ—C1C—H1E	111.6
C2A—C1A—H1B	111.5	C2C—C1C—H1F	111.6
C8Aⁱ—C1A—H1B	111.5	C8Cⁱⁱⁱ—C1C—H1F	111.6
H1A—C1A—H1B	109.3	H1E—C1C—H1F	109.4
C2Aⁱ—C2A—C3A	109.8 (3)	C2Cⁱⁱⁱ—C2C—C3C	109.6 (3)
C2Aⁱ—C2A—C1A	111.8 (3)	C2Cⁱⁱⁱ—C2C—C1C	113.0 (4)
C3A—C2A—C1A	138.4 (2)	C3C—C2C—C1C	137.4 (2)
C4A—C3A—C8A	120.1 (3)	C4C—C3C—C8C	120.1 (3)
C4A—C3A—C2A	132.5 (3)	C4C—C3C—C2C	133.1 (3)
C8A—C3A—C2A	107.5 (2)	C8C—C3C—C2C	106.8 (2)
C5A—C4A—C3A	118.5 (3)	C5C—C4C—C3C	118.6 (3)
C5A—C4A—H4A	120.7	C5C—C4C—H4C	120.7
C3A—C4A—H4A	120.7	C3C—C4C—H4C	120.7
C6A—C5A—C4A	120.9 (3)	C6C—C5C—C4C	120.4 (3)
C6A—C5A—H5A	119.6	C6C—C5C—H5C	119.8
C4A—C5A—H5A	119.6	C4C—C5C—H5C	119.8
C5A—C6A—C7A	121.2 (3)	C5C—C6C—C7C	121.1 (3)
C5A—C6A—H6A	119.4	C5C—C6C—H6C	119.5
C7A—C6A—H6A	119.4	C7C—C6C—H6C	119.5
C8A—C7A—C6A	118.6 (3)	C8C—C7C—C6C	119.3 (3)
C8A—C7A—H7A	120.7	C8C—C7C—H7C	120.3
C6A—C7A—H7A	120.7	C6C—C7C—H7C	120.3
C7A—C8A—C3A	120.7 (3)	C7C—C8C—C3C	120.5 (3)
C7A—C8A—C1Aⁱ	129.7 (3)	C7C—C8C—C1Cⁱⁱⁱ	129.5 (3)
C3A—C8A—C1Aⁱ	109.6 (3)	C3C—C8C—C1Cⁱⁱⁱ	109.9 (3)
C2B—C1B—C8Bⁱⁱ	101.0 (2)	C2D—C1D—C8D^iv	100.7 (2)
C2B—C1B—H1C	111.6	C2D—C1D—H1G	111.6
C8Bⁱⁱ—C1B—H1C	111.6	C8D^iv—C1D—H1G	111.6
C2B—C1B—H1D	111.6	C2D—C1D—H1H	111.6
C8Bⁱⁱ—C1B—H1D	111.6	C8D^iv—C1D—H1H	111.6
H1C—C1B—H1D	109.4	H1G—C1D—H1H	109.4
C2Bⁱⁱ—C2B—C3B	109.3 (4)	C2D^iv—C2D—C3D	109.2 (4)
C2Bⁱⁱ—C2B—C1B	112.7 (4)	C2D^iv—C2D—C1D	113.2 (4)
C3B—C2B—C1B	138.0 (2)	C3D—C2D—C1D	137.5 (2)
C4B—C3B—C8B	120.6 (3)	C4D—C3D—C8D	120.2 (3)
C4B—C3B—C2B	132.7 (3)	C4D—C3D—C2D	132.9 (3)
C8B—C3B—C2B	106.7 (2)	C8D—C3D—C2D	106.9 (3)
C5B—C4B—C3B	118.7 (3)	C5D—C4D—C3D	118.5 (3)
C5B—C4B—H4B	120.7	C5D—C4D—H4D	120.8
C3B—C4B—H4B	120.7	C3D—C4D—H4D	120.8
C4B—C5B—C6B	121.5 (3)	C6D—C5D—C4D	120.3 (3)
C4B—C5B—H5B	119.3	C6D—C5D—H5D	119.8
C6B—C5B—H5B	119.3	C4D—C5D—H5D	119.8
C5B—C6B—C7B	120.5 (3)	C5D—C6D—C7D	120.7 (3)
C5B—C6B—H6B	119.7	C5D—C6D—H6D	119.6
C7B—C6B—H6B	119.7	C7D—C6D—H6D	119.6
C8B—C7B—C6B	118.5 (3)	C8D—C7D—C6D	119.6 (3)
C8B—C7B—H7B	120.7	C8D—C7D—H7D	120.2
C6B—C7B—H7B	120.7	C6D—C7D—H7D	120.2
C7B—C8B—C3B	120.2 (3)	C7D—C8D—C3D	120.7 (3)
C7B—C8B—C1Bⁱⁱ	129.5 (3)	C7D—C8D—C1D^iv	129.4 (3)
C3B—C8B—C1Bⁱⁱ	110.3 (3)	C3D—C8D—C1D^iv	109.9 (3)

C8Aⁱ—C1A—C2A—C2Aⁱ	−0.1 (3)	C8Cⁱⁱⁱ—C1C—C2C—C2Cⁱⁱⁱ	0.0 (4)
C8Aⁱ—C1A—C2A—C3A	−179.9 (3)	C8Cⁱⁱⁱ—C1C—C2C—C3C	−180.0 (3)
C2Aⁱ—C2A—C3A—C4A	−178.8 (3)	C2Cⁱⁱⁱ—C2C—C3C—C4C	−179.4 (3)
C1A—C2A—C3A—C4A	1.0 (5)	C1C—C2C—C3C—C4C	0.6 (5)
C2Aⁱ—C2A—C3A—C8A	0.1 (3)	C2Cⁱⁱⁱ—C2C—C3C—C8C	0.0 (3)
C1A—C2A—C3A—C8A	179.9 (3)	C1C—C2C—C3C—C8C	−180.0 (3)
C8A—C3A—C4A—C5A	−0.5 (4)	C8C—C3C—C4C—C5C	0.2 (4)
C2A—C3A—C4A—C5A	178.3 (3)	C2C—C3C—C4C—C5C	179.5 (3)
C3A—C4A—C5A—C6A	0.7 (4)	C3C—C4C—C5C—C6C	0.4 (4)
C4A—C5A—C6A—C7A	−0.4 (4)	C4C—C5C—C6C—C7C	−0.5 (4)
C5A—C6A—C7A—C8A	−0.1 (4)	C5C—C6C—C7C—C8C	0.0 (4)
C6A—C7A—C8A—C3A	0.3 (4)	C6C—C7C—C8C—C3C	0.6 (4)
C6A—C7A—C8A—C1Aⁱ	−178.5 (2)	C6C—C7C—C8C—C1Cⁱⁱⁱ	−179.6 (2)
C4A—C3A—C8A—C7A	0.0 (4)	C4C—C3C—C8C—C7C	−0.7 (4)
C2A—C3A—C8A—C7A	−179.1 (2)	C2C—C3C—C8C—C7C	179.8 (2)
C4A—C3A—C8A—C1Aⁱ	179.0 (2)	C4C—C3C—C8C—C1Cⁱⁱⁱ	179.5 (2)
C2A—C3A—C8A—C1Aⁱ	−0.1 (3)	C2C—C3C—C8C—C1Cⁱⁱⁱ	0.0 (3)
C8Bⁱⁱ—C1B—C2B—C2Bⁱⁱ	0.2 (4)	C8D^iv—C1D—C2D—C2D^iv	−0.7 (4)
C8Bⁱⁱ—C1B—C2B—C3B	179.7 (3)	C8D^iv—C1D—C2D—C3D	−179.7 (3)
C2Bⁱⁱ—C2B—C3B—C4B	179.1 (3)	C2D^iv—C2D—C3D—C4D	179.8 (3)
C1B—C2B—C3B—C4B	−0.4 (5)	C1D—C2D—C3D—C4D	−1.2 (5)
C2Bⁱⁱ—C2B—C3B—C8B	−0.4 (4)	C2D^iv—C2D—C3D—C8D	0.4 (4)
C1B—C2B—C3B—C8B	−179.9 (3)	C1D—C2D—C3D—C8D	179.4 (3)
C8B—C3B—C4B—C5B	0.6 (4)	C8D—C3D—C4D—C5D	−0.8 (4)
C2B—C3B—C4B—C5B	−178.9 (3)	C2D—C3D—C4D—C5D	179.9 (3)
C3B—C4B—C5B—C6B	−0.9 (4)	C3D—C4D—C5D—C6D	−0.4 (4)
C4B—C5B—C6B—C7B	0.7 (4)	C4D—C5D—C6D—C7D	1.2 (4)
C5B—C6B—C7B—C8B	−0.3 (4)	C5D—C6D—C7D—C8D	−0.8 (4)
C6B—C7B—C8B—C3B	0.0 (4)	C6D—C7D—C8D—C3D	−0.3 (4)
C6B—C7B—C8B—C1Bⁱⁱ	178.9 (3)	C6D—C7D—C8D—C1D^iv	−179.6 (3)
C4B—C3B—C8B—C7B	−0.2 (4)	C4D—C3D—C8D—C7D	1.1 (4)
C2B—C3B—C8B—C7B	179.4 (2)	C2D—C3D—C8D—C7D	−179.4 (2)
C4B—C3B—C8B—C1Bⁱⁱ	−179.3 (2)	C4D—C3D—C8D—C1D^iv	−179.5 (2)
C2B—C3B—C8B—C1Bⁱⁱ	0.3 (3)	C2D—C3D—C8D—C1D^iv	0.0 (3)

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

Acknowledgements

The authors are grateful to N. Jacobs for the preparation of the title compound.

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