(E)-3,3',4,4',7,7',8,8'-Octa-methyl-2H,2'H-1,1'-bi(cyclo-penta-[fg]acenaphthyl-enyl-idene)-2,2',5,5',6,6'-hexa-one dichloro-methane monosolvate.

The title compound, C(36)H(24)O(6)·CH(2)Cl(2), is a dimer of two essentially planar (r.m.s., deviations of fitted plane of 14 pyracene C atoms = 0.0539 and 0.0543 Å) tetra-cyclic pyracene frameworks (each with four methyl groups and three carbonyl groups on the peripheral carbon atoms) twisted along a central C=C bond with an angle of 50.78 (3)° at 90 K. There are notably long Csp(2)-Csp(2) bonds associated with the carbonyl groups, the longest being 1.601 (3) Å between two carbonyl C atoms. There are also intermolecular carbonyl⋯carbonyl interactions of both parallel and antiparallel types, with C⋯O distances in the range 3.041 (3) to 3.431 (2) Å. This compound is of inter-est with respect to the synthesis of fullerene fragments, such as corannulene and semibuckminsterfullerene derivatives (or 'buckybowls'), and is a side product of the previously reported oxidation reaction. Structural details, such as planarity analysis of fused rings, out-of-plane deviation of substituents, inter-molecular inter-actions, and longer than typical bond lengths, will be discussed as well as comparisons to structurally related compounds.

Related literature

For the synthesis of fullerene fragments, see the following recent reviews: Tsefrikas & Scott (2006 ▶); Wu & Siegel (2006 ▶); Sygula (2011 ▶). For structurally related compounds, see also: Abdourazak et al. (1994 ▶); Sygula et al. (1997 ▶); Mehta et al. (1999 ▶); Kilway et al. (2004 ▶). For a description of the Cambridge Crystallographic Database, see: Allen (2002 ▶). For tables of van der Waals radii, see: Bondi (1964 ▶). For inter­molecular carbonyl group inter­actions, see: Allen et al. (1998 ▶).

Experimental

Crystal data

C36H24O6·CH2Cl2

M = 637.48

Triclinic,

a = 8.6644 (15) Å

b = 10.959 (2) Å

c = 15.856 (3) Å

α = 94.241 (10)°

β = 101.501 (9)°

γ = 95.204 (10)°

V = 1462.7 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.27 mm−1

T = 90 K

0.33 × 0.27 × 0.17 mm

Data collection

Nonius KappaCCD diffractometer (with an Oxford Cryosystems cryostream cooler)

Absorption correction: multi-scan (HKL SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.915, T max = 0.956

12739 measured reflections

6679 independent reflections

5001 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.114

S = 1.03

6679 reflections

414 parameters

H-atom parameters constrained

Δρmax = 0.8 e Å−3

Δρmin = −0.40 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶), SXGRAPH (Farrugia, 1999 ▶) and ADDSYM (Spek, 2003 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812016091/mw2064sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812016091/mw2064Isup2.hkl

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

C36H24O6·CH2Cl2	Z = 2
Mr = 637.48	F(000) = 660
Triclinic, P1	Dx = 1.447 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.6644 (15) Å	Cell parameters from 6338 reflections
b = 10.959 (2) Å	θ = 2.6–27.5°
c = 15.856 (3) Å	µ = 0.27 mm−1
α = 94.241 (10)°	T = 90 K
β = 101.501 (9)°	Tabular, red
γ = 95.204 (10)°	0.33 × 0.27 × 0.17 mm
V = 1462.7 (5) Å3

Nonius KappaCCD diffractometer (with an Oxford Cryosystems cryostream cooler)	6679 independent reflections
Radiation source: fine-focus sealed tube	5001 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
Detector resolution: 9 pixels mm-1	θmax = 27.5°, θmin = 2.6°
CCD scans	h = −11→11
Absorption correction: multi-scan (HKLSCALEPACK; Otwinowski & Minor, 1997)	k = −14→14
Tmin = 0.915, Tmax = 0.956	l = −20→20
12739 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0463P)2 + 0.9955P] where P = (Fo2 + 2Fc2)/3
6679 reflections	(Δ/σ)max = 0.001
414 parameters	Δρmax = 0.8 e Å−3
0 restraints	Δρmin = −0.40 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
Cl1	0.77328 (7)	−0.03949 (5)	0.77593 (4)	0.03263 (15)
Cl2	0.79071 (6)	0.22106 (5)	0.83069 (4)	0.03157 (15)
O1	0.29471 (15)	0.01404 (12)	0.78727 (8)	0.0189 (3)
O2	−0.40015 (16)	−0.17056 (13)	0.40273 (9)	0.0229 (3)
O3	−0.47615 (16)	0.08134 (13)	0.40444 (9)	0.0241 (3)
O1A	0.25716 (16)	0.42583 (12)	0.66908 (8)	0.0198 (3)
O2A	0.93757 (17)	0.58456 (15)	1.06555 (10)	0.0319 (4)
O3A	0.79850 (17)	0.39242 (15)	1.15279 (9)	0.0278 (4)
C1	0.1538 (2)	0.18790 (17)	0.73469 (12)	0.0149 (4)
C2	0.1864 (2)	0.05194 (17)	0.73837 (12)	0.0148 (4)
C3	0.0352 (2)	−0.14369 (17)	0.63465 (12)	0.0156 (4)
C4	−0.0979 (2)	−0.17981 (17)	0.56337 (12)	0.0158 (4)
C5	−0.3252 (2)	−0.08908 (18)	0.45439 (12)	0.0170 (4)
C6	−0.3647 (2)	0.05076 (18)	0.45374 (12)	0.0175 (4)
C7	−0.2161 (2)	0.24347 (17)	0.56136 (12)	0.0153 (4)
C8	−0.0848 (2)	0.27807 (17)	0.63459 (12)	0.0152 (4)
C9	0.0192 (2)	0.19179 (17)	0.66238 (11)	0.0137 (4)
C10	−0.0186 (2)	0.06873 (17)	0.62502 (11)	0.0139 (4)
C11	0.0713 (2)	−0.01902 (17)	0.66389 (11)	0.0143 (4)
C12	−0.1463 (2)	0.03443 (17)	0.55865 (11)	0.0141 (4)
C13	−0.1852 (2)	−0.09025 (17)	0.52606 (12)	0.0148 (4)
C14	−0.2437 (2)	0.12224 (17)	0.52408 (12)	0.0149 (4)
C15	0.1294 (2)	−0.23962 (18)	0.67640 (13)	0.0213 (4)
H15A	0.2211	−0.1993	0.719	0.032*
H15B	0.1659	−0.29	0.6321	0.032*
H15C	0.0627	−0.2922	0.7053	0.032*
C16	−0.1435 (2)	−0.31386 (17)	0.53295 (13)	0.0199 (4)
H16A	−0.2321	−0.3224	0.4829	0.03*
H16B	−0.1753	−0.3572	0.5797	0.03*
H16C	−0.0528	−0.3494	0.5164	0.03*
C17	−0.3239 (2)	0.33712 (18)	0.52803 (13)	0.0206 (4)
H17A	−0.3994	0.3008	0.4758	0.031*
H17B	−0.2608	0.4089	0.5142	0.031*
H17C	−0.3818	0.3627	0.5723	0.031*
C18	−0.0708 (2)	0.40459 (18)	0.68069 (13)	0.0203 (4)
H18A	−0.0019	0.4068	0.738	0.031*
H18B	−0.1761	0.4248	0.687	0.031*
H18C	−0.0254	0.4647	0.6472	0.031*
C1A	0.2599 (2)	0.28086 (17)	0.78111 (12)	0.0151 (4)
C2A	0.3176 (2)	0.39486 (17)	0.73854 (12)	0.0161 (4)
C3A	0.5858 (2)	0.54462 (18)	0.79525 (13)	0.0192 (4)
C4A	0.7172 (2)	0.57293 (18)	0.86888 (14)	0.0208 (4)
C5A	0.8232 (2)	0.51493 (19)	1.03078 (14)	0.0245 (5)
C6A	0.7485 (2)	0.40834 (19)	1.07795 (13)	0.0204 (4)
C7A	0.4972 (2)	0.24708 (18)	1.01322 (12)	0.0186 (4)
C8A	0.3683 (2)	0.21677 (18)	0.93896 (12)	0.0171 (4)
C9A	0.3677 (2)	0.27995 (17)	0.86501 (12)	0.0156 (4)
C10A	0.4848 (2)	0.37987 (18)	0.86894 (12)	0.0166 (4)
C11A	0.4710 (2)	0.44799 (17)	0.79784 (12)	0.0160 (4)
C12A	0.6036 (2)	0.41108 (18)	0.94072 (12)	0.0180 (4)
C13A	0.7207 (2)	0.50925 (18)	0.94145 (13)	0.0207 (4)
C14A	0.6118 (2)	0.34447 (19)	1.01342 (12)	0.0187 (4)
C15A	0.5742 (2)	0.61827 (19)	0.71843 (14)	0.0238 (5)
H15D	0.4867	0.5802	0.6723	0.036*
H15E	0.6736	0.6201	0.6977	0.036*
H15F	0.5547	0.7025	0.7352	0.036*
C16A	0.8495 (2)	0.6702 (2)	0.86588 (16)	0.0280 (5)
H16D	0.9166	0.6892	0.9238	0.042*
H16E	0.805	0.7447	0.8462	0.042*
H16F	0.9132	0.64	0.8258	0.042*
C17A	0.5073 (2)	0.1721 (2)	1.08941 (13)	0.0246 (5)
H17D	0.6081	0.1969	1.1302	0.037*
H17E	0.5011	0.0846	1.0695	0.037*
H17F	0.4194	0.1859	1.1181	0.037*
C18A	0.2343 (2)	0.12270 (19)	0.94566 (13)	0.0214 (4)
H18D	0.1407	0.1326	0.9015	0.032*
H18E	0.2093	0.1345	1.0031	0.032*
H18F	0.2658	0.0398	0.9367	0.032*
C19	0.6709 (2)	0.0932 (2)	0.76933 (15)	0.0276 (5)
H19A	0.6416	0.1108	0.7082	0.033*
H19B	0.5723	0.0781	0.7913	0.033*

	U11	U22	U33	U12	U13	U23
Cl1	0.0365 (3)	0.0235 (3)	0.0423 (3)	0.0051 (2)	0.0160 (3)	0.0086 (2)
Cl2	0.0280 (3)	0.0299 (3)	0.0350 (3)	0.0006 (2)	0.0079 (2)	−0.0095 (2)
O1	0.0185 (7)	0.0184 (7)	0.0186 (7)	0.0039 (5)	−0.0002 (5)	0.0033 (6)
O2	0.0218 (7)	0.0223 (8)	0.0211 (7)	−0.0023 (6)	0.0003 (6)	−0.0035 (6)
O3	0.0206 (7)	0.0259 (8)	0.0221 (8)	0.0027 (6)	−0.0039 (6)	0.0006 (6)
O1A	0.0241 (7)	0.0181 (7)	0.0148 (7)	0.0007 (6)	−0.0010 (5)	0.0013 (5)
O2A	0.0210 (8)	0.0343 (9)	0.0343 (9)	0.0041 (7)	−0.0043 (7)	−0.0110 (7)
O3A	0.0239 (8)	0.0415 (9)	0.0158 (7)	0.0114 (7)	−0.0029 (6)	−0.0009 (6)
C1	0.0144 (9)	0.0153 (9)	0.0149 (9)	0.0016 (7)	0.0027 (7)	0.0021 (7)
C2	0.0145 (9)	0.0168 (9)	0.0131 (9)	0.0009 (7)	0.0027 (7)	0.0029 (7)
C3	0.0178 (9)	0.0160 (10)	0.0139 (9)	0.0016 (7)	0.0049 (7)	0.0018 (7)
C4	0.0184 (9)	0.0148 (9)	0.0147 (9)	−0.0004 (7)	0.0055 (7)	0.0013 (7)
C5	0.0168 (9)	0.0191 (10)	0.0148 (9)	−0.0005 (8)	0.0040 (7)	0.0002 (8)
C6	0.0147 (9)	0.0231 (10)	0.0138 (9)	0.0001 (8)	0.0020 (7)	0.0019 (8)
C7	0.0142 (9)	0.0163 (10)	0.0152 (9)	0.0013 (7)	0.0019 (7)	0.0029 (7)
C8	0.0159 (9)	0.0151 (9)	0.0143 (9)	−0.0004 (7)	0.0029 (7)	0.0018 (7)
C9	0.0147 (9)	0.0141 (9)	0.0119 (9)	0.0000 (7)	0.0023 (7)	0.0016 (7)
C10	0.0145 (9)	0.0145 (9)	0.0129 (9)	0.0000 (7)	0.0039 (7)	0.0014 (7)
C11	0.0151 (9)	0.0164 (9)	0.0117 (9)	0.0020 (7)	0.0030 (7)	0.0022 (7)
C12	0.0151 (9)	0.0154 (9)	0.0120 (9)	−0.0002 (7)	0.0042 (7)	0.0013 (7)
C13	0.0155 (9)	0.0150 (9)	0.0130 (9)	−0.0017 (7)	0.0031 (7)	−0.0006 (7)
C14	0.0131 (8)	0.0176 (10)	0.0133 (9)	0.0004 (7)	0.0018 (7)	0.0022 (7)
C15	0.0289 (11)	0.0156 (10)	0.0185 (10)	0.0045 (8)	0.0016 (8)	0.0017 (8)
C16	0.0257 (10)	0.0150 (10)	0.0185 (10)	0.0003 (8)	0.0039 (8)	0.0020 (8)
C17	0.0184 (10)	0.0178 (10)	0.0226 (10)	0.0029 (8)	−0.0021 (8)	0.0000 (8)
C18	0.0205 (10)	0.0155 (10)	0.0227 (10)	0.0039 (8)	−0.0012 (8)	−0.0003 (8)
C1A	0.0146 (9)	0.0168 (10)	0.0136 (9)	0.0037 (7)	0.0014 (7)	0.0010 (7)
C2A	0.0174 (9)	0.0155 (9)	0.0146 (9)	0.0027 (7)	0.0026 (7)	−0.0026 (7)
C3A	0.0185 (9)	0.0161 (10)	0.0233 (10)	0.0033 (8)	0.0061 (8)	−0.0017 (8)
C4A	0.0137 (9)	0.0159 (10)	0.0313 (11)	0.0032 (8)	0.0033 (8)	−0.0055 (8)
C5A	0.0161 (10)	0.0238 (11)	0.0308 (12)	0.0053 (8)	0.0013 (8)	−0.0109 (9)
C6A	0.0162 (9)	0.0264 (11)	0.0175 (10)	0.0093 (8)	−0.0002 (8)	−0.0039 (8)
C7A	0.0196 (10)	0.0232 (11)	0.0135 (9)	0.0100 (8)	0.0019 (7)	−0.0002 (8)
C8A	0.0181 (9)	0.0190 (10)	0.0145 (9)	0.0063 (8)	0.0027 (7)	−0.0004 (8)
C9A	0.0150 (9)	0.0160 (9)	0.0154 (9)	0.0052 (7)	0.0019 (7)	−0.0018 (7)
C10A	0.0142 (9)	0.0187 (10)	0.0159 (9)	0.0037 (7)	0.0013 (7)	−0.0028 (8)
C11A	0.0155 (9)	0.0148 (9)	0.0167 (9)	0.0029 (7)	0.0014 (7)	−0.0016 (7)
C12A	0.0157 (9)	0.0205 (10)	0.0166 (10)	0.0075 (8)	−0.0003 (7)	−0.0036 (8)
C13A	0.0141 (9)	0.0203 (10)	0.0253 (11)	0.0063 (8)	0.0000 (8)	−0.0076 (8)
C14A	0.0166 (9)	0.0245 (11)	0.0139 (9)	0.0086 (8)	−0.0006 (7)	−0.0036 (8)
C15A	0.0259 (11)	0.0192 (11)	0.0273 (11)	0.0008 (8)	0.0092 (9)	0.0012 (9)
C16A	0.0190 (10)	0.0215 (11)	0.0414 (13)	−0.0001 (8)	0.0033 (9)	0.0003 (10)
C17A	0.0257 (11)	0.0310 (12)	0.0172 (10)	0.0099 (9)	0.0009 (8)	0.0043 (9)
C18A	0.0210 (10)	0.0251 (11)	0.0185 (10)	0.0034 (8)	0.0040 (8)	0.0038 (8)
C19	0.0209 (10)	0.0264 (12)	0.0328 (12)	0.0014 (9)	−0.0001 (9)	0.0017 (9)

Cl1—C19	1.769 (2)	C18—H18A	0.98
Cl2—C19	1.766 (2)	C18—H18B	0.98
O1—C2	1.217 (2)	C18—H18C	0.98
O2—C5	1.210 (2)	C1A—C9A	1.466 (3)
O3—C6	1.205 (2)	C1A—C2A	1.553 (3)
O1A—C2A	1.208 (2)	C2A—C11A	1.507 (3)
O2A—C5A	1.205 (2)	C3A—C11A	1.394 (3)
O3A—C6A	1.211 (2)	C3A—C4A	1.452 (3)
C1—C1A	1.369 (3)	C3A—C15A	1.502 (3)
C1—C9	1.470 (2)	C4A—C13A	1.386 (3)
C1—C2	1.545 (3)	C4A—C16A	1.503 (3)
C2—C11	1.500 (2)	C5A—C13A	1.508 (3)
C3—C11	1.397 (3)	C5A—C6A	1.590 (3)
C3—C4	1.448 (3)	C6A—C14A	1.483 (3)
C3—C15	1.501 (3)	C7A—C14A	1.390 (3)
C4—C13	1.388 (3)	C7A—C8A	1.447 (3)
C4—C16	1.504 (3)	C7A—C17A	1.503 (3)
C5—C13	1.489 (3)	C8A—C9A	1.404 (3)
C5—C6	1.601 (3)	C8A—C18A	1.507 (3)
C6—C14	1.487 (2)	C9A—C10A	1.413 (3)
C7—C14	1.393 (3)	C10A—C12A	1.372 (3)
C7—C8	1.455 (2)	C10A—C11A	1.389 (3)
C7—C17	1.504 (3)	C12A—C14A	1.403 (3)
C8—C9	1.399 (3)	C12A—C13A	1.408 (3)
C8—C18	1.502 (3)	C15A—H15D	0.98
C9—C10	1.415 (3)	C15A—H15E	0.98
C10—C12	1.369 (2)	C15A—H15F	0.98
C10—C11	1.394 (3)	C16A—H16D	0.98
C12—C14	1.407 (3)	C16A—H16E	0.98
C12—C13	1.411 (3)	C16A—H16F	0.98
C15—H15A	0.98	C17A—H17D	0.98
C15—H15B	0.98	C17A—H17E	0.98
C15—H15C	0.98	C17A—H17F	0.98
C16—H16A	0.98	C18A—H18D	0.98
C16—H16B	0.98	C18A—H18E	0.98
C16—H16C	0.98	C18A—H18F	0.98
C17—H17A	0.98	C19—H19A	0.99
C17—H17B	0.98	C19—H19B	0.99
C17—H17C	0.98
C1A—C1—C9	130.36 (17)	O1A—C2A—C11A	128.50 (18)
C1A—C1—C2	121.11 (16)	O1A—C2A—C1A	126.17 (16)
C9—C1—C2	107.09 (15)	C11A—C2A—C1A	105.05 (15)
O1—C2—C11	127.71 (18)	C11A—C3A—C4A	118.41 (18)
O1—C2—C1	125.78 (17)	C11A—C3A—C15A	121.03 (17)
C11—C2—C1	106.15 (15)	C4A—C3A—C15A	120.57 (17)
C11—C3—C4	118.54 (17)	C13A—C4A—C3A	119.75 (18)
C11—C3—C15	121.45 (16)	C13A—C4A—C16A	120.26 (18)
C4—C3—C15	120.00 (17)	C3A—C4A—C16A	119.99 (19)
C13—C4—C3	119.39 (17)	O2A—C5A—C13A	130.6 (2)
C13—C4—C16	120.90 (17)	O2A—C5A—C6A	122.96 (19)
C3—C4—C16	119.67 (17)	C13A—C5A—C6A	106.45 (16)
O2—C5—C13	131.33 (18)	O3A—C6A—C14A	131.1 (2)
O2—C5—C6	122.48 (17)	O3A—C6A—C5A	122.96 (18)
C13—C5—C6	106.18 (15)	C14A—C6A—C5A	105.93 (16)
O3—C6—C14	131.56 (19)	C14A—C7A—C8A	119.88 (17)
O3—C6—C5	122.29 (17)	C14A—C7A—C17A	120.33 (17)
C14—C6—C5	106.12 (15)	C8A—C7A—C17A	119.78 (18)
C14—C7—C8	119.45 (17)	C9A—C8A—C7A	119.36 (18)
C14—C7—C17	120.39 (16)	C9A—C8A—C18A	122.13 (17)
C8—C7—C17	120.13 (17)	C7A—C8A—C18A	118.43 (17)
C9—C8—C7	119.59 (17)	C8A—C9A—C10A	118.45 (17)
C9—C8—C18	122.17 (16)	C8A—C9A—C1A	135.94 (17)
C7—C8—C18	118.17 (17)	C10A—C9A—C1A	105.09 (16)
C8—C9—C10	118.30 (16)	C12A—C10A—C11A	121.38 (18)
C8—C9—C1	135.75 (17)	C12A—C10A—C9A	121.74 (18)
C10—C9—C1	104.98 (16)	C11A—C10A—C9A	116.85 (16)
C12—C10—C11	120.79 (17)	C10A—C11A—C3A	120.23 (17)
C12—C10—C9	121.98 (17)	C10A—C11A—C2A	105.24 (16)
C11—C10—C9	116.98 (16)	C3A—C11A—C2A	134.50 (18)
C10—C11—C3	120.70 (16)	C10A—C12A—C14A	120.61 (18)
C10—C11—C2	104.74 (16)	C10A—C12A—C13A	120.15 (19)
C3—C11—C2	134.36 (17)	C14A—C12A—C13A	119.23 (17)
C10—C12—C14	120.52 (17)	C4A—C13A—C12A	119.78 (17)
C10—C12—C13	120.37 (17)	C4A—C13A—C5A	136.86 (18)
C14—C12—C13	119.07 (16)	C12A—C13A—C5A	103.36 (17)
C4—C13—C12	120.16 (16)	C7A—C14A—C12A	119.69 (17)
C4—C13—C5	135.69 (17)	C7A—C14A—C6A	135.27 (18)
C12—C13—C5	104.14 (16)	C12A—C14A—C6A	104.90 (17)
C7—C14—C12	119.68 (16)	C3A—C15A—H15D	109.5
C7—C14—C6	135.84 (17)	C3A—C15A—H15E	109.5
C12—C14—C6	104.37 (16)	H15D—C15A—H15E	109.5
C3—C15—H15A	109.5	C3A—C15A—H15F	109.5
C3—C15—H15B	109.5	H15D—C15A—H15F	109.5
H15A—C15—H15B	109.5	H15E—C15A—H15F	109.5
C3—C15—H15C	109.5	C4A—C16A—H16D	109.5
H15A—C15—H15C	109.5	C4A—C16A—H16E	109.5
H15B—C15—H15C	109.5	H16D—C16A—H16E	109.5
C4—C16—H16A	109.5	C4A—C16A—H16F	109.5
C4—C16—H16B	109.5	H16D—C16A—H16F	109.5
H16A—C16—H16B	109.5	H16E—C16A—H16F	109.5
C4—C16—H16C	109.5	C7A—C17A—H17D	109.5
H16A—C16—H16C	109.5	C7A—C17A—H17E	109.5
H16B—C16—H16C	109.5	H17D—C17A—H17E	109.5
C7—C17—H17A	109.5	C7A—C17A—H17F	109.5
C7—C17—H17B	109.5	H17D—C17A—H17F	109.5
H17A—C17—H17B	109.5	H17E—C17A—H17F	109.5
C7—C17—H17C	109.5	C8A—C18A—H18D	109.5
H17A—C17—H17C	109.5	C8A—C18A—H18E	109.5
H17B—C17—H17C	109.5	H18D—C18A—H18E	109.5
C8—C18—H18A	109.5	C8A—C18A—H18F	109.5
C8—C18—H18B	109.5	H18D—C18A—H18F	109.5
H18A—C18—H18B	109.5	H18E—C18A—H18F	109.5
C8—C18—H18C	109.5	Cl2—C19—Cl1	110.44 (11)
H18A—C18—H18C	109.5	Cl2—C19—H19A	109.6
H18B—C18—H18C	109.5	Cl1—C19—H19A	109.6
C1—C1A—C9A	128.93 (17)	Cl2—C19—H19B	109.6
C1—C1A—C2A	121.74 (16)	Cl1—C19—H19B	109.6
C9A—C1A—C2A	107.35 (15)	H19A—C19—H19B	108.1
C1A—C1—C2—O1	8.3 (3)	C9—C1—C1A—C2A	−34.6 (3)
C9—C1—C2—O1	175.94 (18)	C2—C1—C1A—C2A	129.85 (19)
C1A—C1—C2—C11	−165.24 (17)	C1—C1A—C2A—O1A	15.1 (3)
C9—C1—C2—C11	2.42 (19)	C9A—C1A—C2A—O1A	−179.58 (19)
C11—C3—C4—C13	0.2 (3)	C1—C1A—C2A—C11A	−159.24 (18)
C15—C3—C4—C13	179.21 (18)	C9A—C1A—C2A—C11A	6.1 (2)
C11—C3—C4—C16	−177.50 (17)	C11A—C3A—C4A—C13A	−3.9 (3)
C15—C3—C4—C16	1.5 (3)	C15A—C3A—C4A—C13A	175.87 (19)
O2—C5—C6—O3	3.8 (3)	C11A—C3A—C4A—C16A	175.50 (19)
C13—C5—C6—O3	−177.47 (18)	C15A—C3A—C4A—C16A	−4.7 (3)
O2—C5—C6—C14	−177.87 (17)	O2A—C5A—C6A—O3A	2.4 (3)
C13—C5—C6—C14	0.89 (19)	C13A—C5A—C6A—O3A	−175.95 (19)
C14—C7—C8—C9	4.9 (3)	O2A—C5A—C6A—C14A	−179.79 (19)
C17—C7—C8—C9	−176.94 (17)	C13A—C5A—C6A—C14A	1.9 (2)
C14—C7—C8—C18	−172.07 (17)	C14A—C7A—C8A—C9A	5.1 (3)
C17—C7—C8—C18	6.1 (3)	C17A—C7A—C8A—C9A	−174.21 (18)
C7—C8—C9—C10	−7.9 (3)	C14A—C7A—C8A—C18A	−171.57 (18)
C18—C8—C9—C10	168.99 (17)	C17A—C7A—C8A—C18A	9.1 (3)
C7—C8—C9—C1	−174.67 (19)	C7A—C8A—C9A—C10A	−6.4 (3)
C18—C8—C9—C1	2.2 (3)	C18A—C8A—C9A—C10A	170.20 (18)
C1A—C1—C9—C8	−28.1 (4)	C7A—C8A—C9A—C1A	−176.7 (2)
C2—C1—C9—C8	165.8 (2)	C18A—C8A—C9A—C1A	−0.1 (4)
C1A—C1—C9—C10	163.9 (2)	C1—C1A—C9A—C8A	−28.4 (4)
C2—C1—C9—C10	−2.20 (19)	C2A—C1A—C9A—C8A	167.7 (2)
C8—C9—C10—C12	5.0 (3)	C1—C1A—C9A—C10A	160.4 (2)
C1—C9—C10—C12	175.54 (17)	C2A—C1A—C9A—C10A	−3.5 (2)
C8—C9—C10—C11	−169.25 (17)	C8A—C9A—C10A—C12A	4.2 (3)
C1—C9—C10—C11	1.3 (2)	C1A—C9A—C10A—C12A	177.22 (18)
C12—C10—C11—C3	1.5 (3)	C8A—C9A—C10A—C11A	−173.62 (18)
C9—C10—C11—C3	175.82 (17)	C1A—C9A—C10A—C11A	−0.6 (2)
C12—C10—C11—C2	−174.05 (17)	C12A—C10A—C11A—C3A	5.0 (3)
C9—C10—C11—C2	0.3 (2)	C9A—C10A—C11A—C3A	−177.17 (18)
C4—C3—C11—C10	−0.3 (3)	C12A—C10A—C11A—C2A	−173.30 (18)
C15—C3—C11—C10	−179.24 (18)	C9A—C10A—C11A—C2A	4.5 (2)
C4—C3—C11—C2	173.67 (19)	C4A—C3A—C11A—C10A	−1.1 (3)
C15—C3—C11—C2	−5.3 (3)	C15A—C3A—C11A—C10A	179.16 (18)
O1—C2—C11—C10	−174.99 (19)	C4A—C3A—C11A—C2A	176.7 (2)
C1—C2—C11—C10	−1.65 (19)	C15A—C3A—C11A—C2A	−3.1 (3)
O1—C2—C11—C3	10.4 (3)	O1A—C2A—C11A—C10A	179.6 (2)
C1—C2—C11—C3	−176.3 (2)	C1A—C2A—C11A—C10A	−6.2 (2)
C11—C10—C12—C14	175.13 (17)	O1A—C2A—C11A—C3A	1.7 (4)
C9—C10—C12—C14	1.1 (3)	C1A—C2A—C11A—C3A	175.8 (2)
C11—C10—C12—C13	−2.6 (3)	C11A—C10A—C12A—C14A	177.22 (18)
C9—C10—C12—C13	−176.65 (17)	C9A—C10A—C12A—C14A	−0.5 (3)
C3—C4—C13—C12	−1.3 (3)	C11A—C10A—C12A—C13A	−4.0 (3)
C16—C4—C13—C12	176.37 (17)	C9A—C10A—C12A—C13A	178.34 (18)
C3—C4—C13—C5	−180.0 (2)	C3A—C4A—C13A—C12A	5.0 (3)
C16—C4—C13—C5	−2.3 (3)	C16A—C4A—C13A—C12A	−174.42 (19)
C10—C12—C13—C4	2.5 (3)	C3A—C4A—C13A—C5A	−174.5 (2)
C14—C12—C13—C4	−175.22 (17)	C16A—C4A—C13A—C5A	6.1 (4)
C10—C12—C13—C5	−178.44 (17)	C10A—C12A—C13A—C4A	−1.1 (3)
C14—C12—C13—C5	3.8 (2)	C14A—C12A—C13A—C4A	177.70 (18)
O2—C5—C13—C4	−5.2 (4)	C10A—C12A—C13A—C5A	178.53 (18)
C6—C5—C13—C4	176.2 (2)	C14A—C12A—C13A—C5A	−2.7 (2)
O2—C5—C13—C12	176.1 (2)	O2A—C5A—C13A—C4A	1.6 (4)
C6—C5—C13—C12	−2.54 (19)	C6A—C5A—C13A—C4A	179.8 (2)
C8—C7—C14—C12	1.2 (3)	O2A—C5A—C13A—C12A	−177.9 (2)
C17—C7—C14—C12	−176.97 (17)	C6A—C5A—C13A—C12A	0.2 (2)
C8—C7—C14—C6	176.74 (19)	C8A—C7A—C14A—C12A	−1.4 (3)
C17—C7—C14—C6	−1.4 (3)	C17A—C7A—C14A—C12A	177.92 (18)
C10—C12—C14—C7	−4.2 (3)	C8A—C7A—C14A—C6A	173.6 (2)
C13—C12—C14—C7	173.58 (17)	C17A—C7A—C14A—C6A	−7.1 (3)
C10—C12—C14—C6	179.02 (17)	C10A—C12A—C14A—C7A	−0.9 (3)
C13—C12—C14—C6	−3.2 (2)	C13A—C12A—C14A—C7A	−179.72 (18)
O3—C6—C14—C7	3.3 (4)	C10A—C12A—C14A—C6A	−177.26 (18)
C5—C6—C14—C7	−174.9 (2)	C13A—C12A—C14A—C6A	3.9 (2)
O3—C6—C14—C12	179.3 (2)	O3A—C6A—C14A—C7A	−1.1 (4)
C5—C6—C14—C12	1.16 (19)	C5A—C6A—C14A—C7A	−178.7 (2)
C9—C1—C1A—C9A	163.5 (2)	O3A—C6A—C14A—C12A	174.4 (2)
C2—C1—C1A—C9A	−32.0 (3)	C5A—C6A—C14A—C12A	−3.2 (2)