(Z)-2,3,2',3'-Tetra­hydro-[1,1']­biindenyl­idene

The asymmetric unit in the crystal of the title compound, C₁₈H₁₆, contains two mol­ecules with slightly different conformations. The dihedral angles between the least-squares planes through the C atoms of the phenyl rings in the two mol­ecules are 25.89 (4) and 33.87 (4)°.

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.042
• wR factor = 0.111
• Data-to-parameter ratio = 18.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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S1. Comment

In the course of our investigations on the four possible biindenylidene isomers we already reported a second modification of (E)-2,3,2',3'-tetrahydro-[1,1']biindenylidene (Jovanovic et al., 2001a) and the crystal structure of 1,3,1',3'-tetrahydro-[2,2']biindenylidene (Jovanovic et al., 2001b). The title compound, (I) (Fig. 1), has not been described previously in the literature. Biindilenes are components of many pyrolysis oils and their characterization is important in enviromental analysis. They also represent usefull model substances for MS and NMR analysis, and structural data are important for the understanding of some fine details of MS and NMR spectra.

S2. Experimental

The title compound was obtained from the reaction mixture that contained trans isomer, i.e. (E)-2,3,2',3'-tetrahydro-[1,1']biindenylidene, by two-step chromatography using column chromatography in the first and HPLC in the second step. The reaction mixture was obtained through the reductive coupling of 1H-indan-1-one according to the method of Lenoir & Lemmen (1980). Recrystallization from propan-2-ol gave colourless plates (m.p. 328 K).

S3. Refinement

H atoms were placed in calculated positions with U_iso constrained to be 1.2 times U_eq of the carrier atom.

Computing details

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97, PARST95 (Nardelli, 1995) and PLATON (Spek, 2001).

Figures

Fig. 1. View of the title compound (XP, Sheldrick, 1991) showing the labelling of all non-H atoms. Displacement ellipsoids are shown at the 30% probability level. H atoms are drawn as circles of arbitrary radii.

(I)

Crystal data

C18H16	Dx = 1.204 Mg m^−3
Mr = 232.31	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 14231 reflections
a = 14.7176 (2) Å	θ = 3.1–27.5°
b = 14.7680 (2) Å	µ = 0.07 mm^−1
c = 23.5860 (3) Å	T = 291 K
V = 5126.41 (12) Å^3	Block, colourless
Z = 16	0.50 × 0.30 × 0.30 mm
F(000) = 1984

Data collection

Nonius KappaCCD diffractometer	3134 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.036
Graphite monochromator	θmax = 27.5°, θmin = 3.1°
Detector resolution: 10 vertical, 18 horizontal pixels mm^-1	h = −19→19
357 frames via ω–rotation (Δω=1°) with 3 sets at different κ–angles and two times 60 s per frame scans	k = −19→19
5855 measured reflections	l = −30→30
14231 independent reflections

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) = 0.111	H-atom parameters constrained
S = 0.91	w = 1/[σ^2(Fo^2) + (0.061P)^2] where P = (Fo^2 + 2Fc^2)/3
5855 reflections	(Δ/σ)max = 0.001
325 parameters	Δρmax = 0.14 e Å^−3
0 restraints	Δρmin = −0.13 e Å^−3

Special details

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.

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

	x	y	z	Uiso*/Ueq
C1	0.20027 (8)	0.31096 (7)	0.33417 (5)	0.0580 (3)
C2	0.14556 (9)	0.38980 (8)	0.35831 (6)	0.0768 (4)
H2A	0.0951	0.4047	0.3335	0.092*
H2B	0.1836	0.4430	0.3626	0.092*
C3	0.11097 (9)	0.35766 (8)	0.41600 (5)	0.0783 (4)
H3A	0.1485	0.3812	0.4464	0.094*
H3B	0.0486	0.3766	0.4221	0.094*
C4	0.11771 (8)	0.25669 (8)	0.41268 (5)	0.0611 (3)
C5	0.08016 (9)	0.19362 (10)	0.44885 (5)	0.0722 (4)
H5A	0.0478	0.2123	0.4806	0.087*
C6	0.09084 (9)	0.10301 (9)	0.43769 (5)	0.0739 (4)
H6A	0.0668	0.0601	0.4624	0.089*
C7	0.13734 (8)	0.07557 (8)	0.38976 (5)	0.0662 (4)
H7A	0.1431	0.0141	0.3819	0.079*
C8	0.17513 (8)	0.13801 (8)	0.35357 (5)	0.0587 (3)
H8A	0.2053	0.1187	0.3211	0.070*
C9	0.16831 (7)	0.22997 (8)	0.36537 (4)	0.0533 (3)
C11	0.26309 (8)	0.32239 (7)	0.29351 (5)	0.0558 (3)
C12	0.27676 (10)	0.41267 (7)	0.26371 (5)	0.0748 (4)
H12A	0.3165	0.4515	0.2857	0.090*
H12B	0.2190	0.4433	0.2585	0.090*
C13	0.31972 (10)	0.39022 (8)	0.20656 (5)	0.0767 (4)
H13A	0.2750	0.3928	0.1764	0.092*
H13B	0.3688	0.4318	0.1979	0.092*
C14	0.35463 (8)	0.29618 (8)	0.21408 (5)	0.0602 (3)
C15	0.40957 (9)	0.24724 (10)	0.17801 (5)	0.0767 (4)
H15A	0.4274	0.2719	0.1435	0.092*
C16	0.43788 (9)	0.16208 (10)	0.19320 (6)	0.0795 (4)
H16A	0.4733	0.1283	0.1683	0.095*
C17	0.41396 (8)	0.12623 (8)	0.24534 (6)	0.0716 (4)
H17A	0.4356	0.0696	0.2560	0.086*
C18	0.35805 (8)	0.17418 (8)	0.28177 (5)	0.0600 (3)
H18A	0.3427	0.1503	0.3170	0.072*
C19	0.32498 (8)	0.25876 (7)	0.26516 (4)	0.0526 (3)
C21	0.72005 (8)	0.20233 (7)	0.41483 (5)	0.0536 (3)
C22	0.69592 (9)	0.11535 (7)	0.38350 (5)	0.0700 (4)
H22A	0.7497	0.0786	0.3775	0.084*
H22B	0.6519	0.0803	0.4049	0.084*
C23	0.65589 (9)	0.14592 (8)	0.32712 (5)	0.0709 (4)
H23A	0.7010	0.1428	0.2972	0.085*
H23B	0.6042	0.1087	0.3167	0.085*
C24	0.62725 (8)	0.24193 (8)	0.33761 (4)	0.0570 (3)
C25	0.57129 (9)	0.29636 (9)	0.30503 (5)	0.0695 (4)
H25A	0.5484	0.2753	0.2707	0.083*
C26	0.54973 (9)	0.38185 (9)	0.32374 (5)	0.0727 (4)
H26A	0.5124	0.4188	0.3019	0.087*
C27	0.58341 (9)	0.41327 (8)	0.37506 (5)	0.0668 (4)
H27A	0.5676	0.4708	0.3877	0.080*
C28	0.64006 (8)	0.36000 (7)	0.40752 (5)	0.0582 (3)
H28A	0.6621	0.3814	0.4420	0.070*
C29	0.66425 (7)	0.27360 (7)	0.38837 (4)	0.0513 (3)
C31	0.78309 (8)	0.20507 (7)	0.45581 (5)	0.0544 (3)
C32	0.82550 (9)	0.11976 (7)	0.48076 (5)	0.0695 (4)
H32A	0.8741	0.0977	0.4567	0.083*
H32B	0.7803	0.0724	0.4849	0.083*
C33	0.86245 (9)	0.14824 (8)	0.53862 (5)	0.0703 (4)
H33A	0.8198	0.1335	0.5686	0.084*
H33B	0.9201	0.1189	0.5465	0.084*
C34	0.87398 (8)	0.24868 (8)	0.53313 (5)	0.0569 (3)
C35	0.92439 (9)	0.30565 (9)	0.56701 (5)	0.0688 (4)
H35A	0.9539	0.2833	0.5989	0.083*
C36	0.93065 (9)	0.39621 (9)	0.55318 (5)	0.0732 (4)
H36A	0.9633	0.4355	0.5763	0.088*
C37	0.88828 (9)	0.42847 (8)	0.50484 (5)	0.0675 (4)
H37A	0.8943	0.4892	0.4951	0.081*
C38	0.83737 (8)	0.37186 (7)	0.47097 (5)	0.0574 (3)
H38A	0.8095	0.3943	0.4385	0.069*
C39	0.82779 (8)	0.28109 (7)	0.48554 (4)	0.0516 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0604 (8)	0.0505 (7)	0.0631 (7)	0.0029 (6)	−0.0041 (7)	−0.0122 (6)
C2	0.0728 (9)	0.0578 (8)	0.0997 (10)	0.0063 (7)	0.0040 (8)	−0.0152 (7)
C3	0.0653 (9)	0.0814 (10)	0.0883 (10)	0.0073 (7)	0.0061 (8)	−0.0319 (8)
C4	0.0534 (8)	0.0732 (8)	0.0568 (7)	0.0040 (6)	−0.0021 (6)	−0.0175 (6)
C5	0.0623 (9)	0.1017 (10)	0.0526 (8)	0.0041 (8)	0.0087 (7)	−0.0095 (7)
C6	0.0717 (10)	0.0894 (10)	0.0608 (8)	−0.0014 (8)	0.0038 (7)	0.0102 (7)
C7	0.0686 (9)	0.0652 (8)	0.0649 (8)	0.0020 (7)	0.0039 (7)	0.0048 (6)
C8	0.0615 (8)	0.0584 (7)	0.0562 (7)	0.0016 (6)	0.0073 (6)	−0.0046 (6)
C9	0.0492 (7)	0.0589 (7)	0.0519 (7)	0.0029 (6)	−0.0018 (6)	−0.0083 (6)
C11	0.0620 (8)	0.0485 (7)	0.0568 (7)	−0.0027 (6)	−0.0053 (6)	−0.0058 (5)
C12	0.0850 (10)	0.0541 (8)	0.0851 (9)	−0.0059 (7)	−0.0081 (8)	0.0024 (6)
C13	0.0879 (11)	0.0705 (9)	0.0717 (9)	−0.0205 (8)	−0.0107 (8)	0.0114 (7)
C14	0.0608 (8)	0.0678 (8)	0.0521 (7)	−0.0148 (6)	−0.0039 (6)	−0.0062 (6)
C15	0.0740 (10)	0.0968 (11)	0.0592 (8)	−0.0218 (8)	0.0066 (7)	−0.0090 (8)
C16	0.0658 (9)	0.0937 (11)	0.0791 (10)	−0.0088 (8)	0.0171 (8)	−0.0321 (8)
C17	0.0597 (8)	0.0653 (8)	0.0899 (10)	−0.0015 (7)	0.0046 (8)	−0.0184 (7)
C18	0.0582 (8)	0.0591 (8)	0.0627 (7)	−0.0036 (6)	0.0043 (6)	−0.0066 (6)
C19	0.0544 (7)	0.0516 (7)	0.0518 (7)	−0.0083 (6)	−0.0025 (6)	−0.0062 (5)
C21	0.0568 (7)	0.0480 (7)	0.0560 (7)	−0.0027 (6)	0.0046 (6)	0.0016 (5)
C22	0.0720 (9)	0.0557 (8)	0.0823 (9)	−0.0067 (7)	−0.0014 (7)	−0.0059 (6)
C23	0.0818 (10)	0.0615 (8)	0.0693 (9)	−0.0191 (7)	0.0012 (7)	−0.0110 (6)
C24	0.0588 (8)	0.0594 (7)	0.0530 (7)	−0.0155 (6)	0.0025 (6)	0.0022 (6)
C25	0.0721 (9)	0.0770 (9)	0.0593 (8)	−0.0211 (8)	−0.0102 (7)	0.0087 (7)
C26	0.0670 (9)	0.0742 (9)	0.0770 (9)	−0.0045 (7)	−0.0127 (7)	0.0194 (7)
C27	0.0640 (8)	0.0620 (8)	0.0742 (9)	0.0052 (7)	0.0007 (7)	0.0037 (7)
C28	0.0592 (8)	0.0610 (8)	0.0543 (7)	0.0016 (6)	0.0004 (6)	−0.0021 (6)
C29	0.0514 (7)	0.0521 (7)	0.0504 (7)	−0.0072 (6)	0.0045 (6)	0.0012 (5)
C31	0.0567 (7)	0.0492 (7)	0.0574 (7)	0.0007 (6)	0.0049 (6)	0.0029 (5)
C32	0.0665 (9)	0.0528 (7)	0.0892 (10)	0.0032 (6)	−0.0017 (7)	0.0088 (6)
C33	0.0625 (8)	0.0728 (9)	0.0756 (9)	0.0079 (7)	−0.0019 (7)	0.0206 (7)
C34	0.0520 (7)	0.0670 (8)	0.0517 (7)	0.0083 (6)	0.0039 (6)	0.0046 (6)
C35	0.0638 (9)	0.0886 (10)	0.0539 (7)	0.0141 (8)	−0.0069 (7)	−0.0030 (7)
C36	0.0694 (9)	0.0797 (9)	0.0703 (9)	0.0024 (7)	−0.0098 (7)	−0.0202 (8)
C37	0.0731 (9)	0.0581 (7)	0.0711 (8)	−0.0007 (7)	−0.0040 (8)	−0.0070 (6)
C38	0.0633 (8)	0.0538 (7)	0.0551 (7)	0.0012 (6)	−0.0046 (6)	0.0001 (6)
C39	0.0510 (7)	0.0537 (7)	0.0500 (7)	0.0053 (6)	0.0047 (6)	0.0008 (6)

Geometric parameters (Å, º)

C1—C11	1.3428 (16)	C21—C31	1.3403 (16)
C1—C9	1.4811 (15)	C21—C29	1.4736 (15)
C1—C2	1.5258 (15)	C21—C22	1.5238 (14)
C2—C3	1.5284 (16)	C22—C23	1.5228 (15)
C2—H2A	0.9700	C22—H22A	0.9700
C2—H2B	0.9700	C22—H22B	0.9700
C3—C4	1.4966 (16)	C23—C24	1.4997 (15)
C3—H3A	0.9700	C23—H23A	0.9700
C3—H3B	0.9700	C23—H23B	0.9700
C4—C5	1.3788 (16)	C24—C25	1.3838 (16)
C4—C9	1.3982 (14)	C24—C29	1.3961 (14)
C5—C6	1.3728 (16)	C25—C26	1.3745 (16)
C5—H5A	0.9300	C25—H25A	0.9300
C6—C7	1.3822 (16)	C26—C27	1.3878 (16)
C6—H6A	0.9300	C26—H26A	0.9300
C7—C8	1.3741 (15)	C27—C28	1.3785 (15)
C7—H7A	0.9300	C27—H27A	0.9300
C8—C9	1.3899 (14)	C28—C29	1.3996 (14)
C8—H8A	0.9300	C28—H28A	0.9300
C11—C19	1.4696 (15)	C31—C39	1.4782 (15)
C11—C12	1.5205 (14)	C31—C32	1.5242 (14)
C12—C13	1.5251 (16)	C32—C33	1.5281 (16)
C12—H12A	0.9700	C32—H32A	0.9700
C12—H12B	0.9700	C32—H32B	0.9700
C13—C14	1.4913 (16)	C33—C34	1.4987 (15)
C13—H13A	0.9700	C33—H33A	0.9700
C13—H13B	0.9700	C33—H33B	0.9700
C14—C15	1.3783 (16)	C34—C35	1.3772 (16)
C14—C19	1.3954 (15)	C34—C39	1.3967 (14)
C15—C16	1.3724 (17)	C35—C36	1.3798 (16)
C15—H15A	0.9300	C35—H35A	0.9300
C16—C17	1.3845 (17)	C36—C37	1.3841 (15)
C16—H16A	0.9300	C36—H36A	0.9300
C17—C18	1.3843 (15)	C37—C38	1.3779 (15)
C17—H17A	0.9300	C37—H37A	0.9300
C18—C19	1.3966 (15)	C38—C39	1.3911 (14)
C18—H18A	0.9300	C38—H38A	0.9300
C11—C1—C9	132.46 (10)	C31—C21—C29	132.03 (10)
C11—C1—C2	122.27 (10)	C31—C21—C22	122.44 (10)
C9—C1—C2	105.26 (10)	C29—C21—C22	105.47 (10)
C1—C2—C3	105.72 (10)	C23—C22—C21	105.30 (9)
C1—C2—H2A	110.6	C23—C22—H22A	110.7
C3—C2—H2A	110.6	C21—C22—H22A	110.7
C1—C2—H2B	110.6	C23—C22—H22B	110.7
C3—C2—H2B	110.6	C21—C22—H22B	110.7
H2A—C2—H2B	108.7	H22A—C22—H22B	108.8
C4—C3—C2	103.93 (9)	C24—C23—C22	104.18 (9)
C4—C3—H3A	111.0	C24—C23—H23A	110.9
C2—C3—H3A	111.0	C22—C23—H23A	110.9
C4—C3—H3B	111.0	C24—C23—H23B	110.9
C2—C3—H3B	111.0	C22—C23—H23B	110.9
H3A—C3—H3B	109.0	H23A—C23—H23B	108.9
C5—C4—C9	121.11 (11)	C25—C24—C29	120.91 (11)
C5—C4—C3	127.89 (11)	C25—C24—C23	128.68 (11)
C9—C4—C3	111.00 (11)	C29—C24—C23	110.40 (10)
C6—C5—C4	119.59 (11)	C26—C25—C24	119.51 (11)
C6—C5—H5A	120.2	C26—C25—H25A	120.2
C4—C5—H5A	120.2	C24—C25—H25A	120.2
C5—C6—C7	119.96 (12)	C25—C26—C27	120.32 (12)
C5—C6—H6A	120.0	C25—C26—H26A	119.8
C7—C6—H6A	120.0	C27—C26—H26A	119.8
C8—C7—C6	120.77 (11)	C28—C27—C26	120.63 (11)
C8—C7—H7A	119.6	C28—C27—H27A	119.7
C6—C7—H7A	119.6	C26—C27—H27A	119.7
C7—C8—C9	120.13 (11)	C27—C28—C29	119.66 (11)
C7—C8—H8A	119.9	C27—C28—H28A	120.2
C9—C8—H8A	119.9	C29—C28—H28A	120.2
C8—C9—C4	118.30 (11)	C24—C29—C28	118.88 (10)
C8—C9—C1	131.80 (10)	C24—C29—C21	109.95 (10)
C4—C9—C1	109.74 (10)	C28—C29—C21	131.01 (10)
C1—C11—C19	132.17 (10)	C21—C31—C39	132.31 (10)
C1—C11—C12	122.11 (10)	C21—C31—C32	122.47 (10)
C19—C11—C12	105.57 (10)	C39—C31—C32	105.21 (10)
C11—C12—C13	105.83 (9)	C31—C32—C33	105.25 (9)
C11—C12—H12A	110.6	C31—C32—H32A	110.7
C13—C12—H12A	110.6	C33—C32—H32A	110.7
C11—C12—H12B	110.6	C31—C32—H32B	110.7
C13—C12—H12B	110.6	C33—C32—H32B	110.7
H12A—C12—H12B	108.7	H32A—C32—H32B	108.8
C14—C13—C12	103.90 (9)	C34—C33—C32	103.63 (9)
C14—C13—H13A	111.0	C34—C33—H33A	111.0
C12—C13—H13A	111.0	C32—C33—H33A	111.0
C14—C13—H13B	111.0	C34—C33—H33B	111.0
C12—C13—H13B	111.0	C32—C33—H33B	111.0
H13A—C13—H13B	109.0	H33A—C33—H33B	109.0
C15—C14—C19	120.57 (12)	C35—C34—C39	121.28 (11)
C15—C14—C13	128.10 (12)	C35—C34—C33	127.99 (11)
C19—C14—C13	111.33 (11)	C39—C34—C33	110.70 (10)
C16—C15—C14	119.84 (12)	C34—C35—C36	119.40 (11)
C16—C15—H15A	120.1	C34—C35—H35A	120.3
C14—C15—H15A	120.1	C36—C35—H35A	120.3
C15—C16—C17	120.34 (12)	C35—C36—C37	119.89 (12)
C15—C16—H16A	119.8	C35—C36—H36A	120.1
C17—C16—H16A	119.8	C37—C36—H36A	120.1
C18—C17—C16	120.45 (12)	C38—C37—C36	120.91 (11)
C18—C17—H17A	119.8	C38—C37—H37A	119.5
C16—C17—H17A	119.8	C36—C37—H37A	119.5
C17—C18—C19	119.38 (11)	C37—C38—C39	119.77 (11)
C17—C18—H18A	120.3	C37—C38—H38A	120.1
C19—C18—H18A	120.3	C39—C38—H38A	120.1
C14—C19—C18	119.16 (11)	C38—C39—C34	118.64 (10)
C14—C19—C11	109.47 (10)	C38—C39—C31	131.28 (10)
C18—C19—C11	131.33 (10)	C34—C39—C31	109.74 (10)
C11—C1—C2—C3	−158.94 (11)	C31—C21—C22—C23	−156.57 (11)
C9—C1—C2—C3	20.41 (13)	C29—C21—C22—C23	21.07 (12)
C1—C2—C3—C4	−19.60 (13)	C21—C22—C23—C24	−20.49 (13)
C2—C3—C4—C5	−167.01 (12)	C22—C23—C24—C25	−165.93 (12)
C2—C3—C4—C9	11.98 (14)	C22—C23—C24—C29	12.86 (13)
C9—C4—C5—C6	−1.42 (19)	C29—C24—C25—C26	−1.90 (18)
C3—C4—C5—C6	177.48 (12)	C23—C24—C25—C26	176.78 (11)
C4—C5—C6—C7	−1.4 (2)	C24—C25—C26—C27	−0.33 (19)
C5—C6—C7—C8	1.6 (2)	C25—C26—C27—C28	1.09 (19)
C6—C7—C8—C9	1.11 (18)	C26—C27—C28—C29	0.38 (18)
C7—C8—C9—C4	−3.81 (17)	C25—C24—C29—C28	3.32 (17)
C7—C8—C9—C1	−178.71 (12)	C23—C24—C29—C28	−175.58 (10)
C5—C4—C9—C8	4.00 (17)	C25—C24—C29—C21	179.36 (10)
C3—C4—C9—C8	−175.07 (10)	C23—C24—C29—C21	0.46 (13)
C5—C4—C9—C1	179.96 (11)	C27—C28—C29—C24	−2.53 (16)
C3—C4—C9—C1	0.89 (14)	C27—C28—C29—C21	−177.60 (11)
C11—C1—C9—C8	−19.0 (2)	C31—C21—C29—C24	163.67 (12)
C2—C1—C9—C8	161.75 (12)	C22—C21—C29—C24	−13.66 (12)
C11—C1—C9—C4	165.78 (13)	C31—C21—C29—C28	−20.9 (2)
C2—C1—C9—C4	−13.47 (13)	C22—C21—C29—C28	161.75 (11)
C9—C1—C11—C19	−1.1 (2)	C29—C21—C31—C39	−7.8 (2)
C2—C1—C11—C19	178.09 (11)	C22—C21—C31—C39	169.12 (11)
C9—C1—C11—C12	173.63 (11)	C29—C21—C31—C32	173.48 (11)
C2—C1—C11—C12	−7.23 (18)	C22—C21—C31—C32	−9.57 (18)
C1—C11—C12—C13	−155.96 (11)	C21—C31—C32—C33	−158.52 (11)
C19—C11—C12—C13	19.95 (13)	C39—C31—C32—C33	22.49 (12)
C11—C12—C13—C14	−17.36 (13)	C31—C32—C33—C34	−22.36 (13)
C12—C13—C14—C15	−170.94 (12)	C32—C33—C34—C35	−163.15 (12)
C12—C13—C14—C19	8.72 (13)	C32—C33—C34—C39	14.58 (13)
C19—C14—C15—C16	−2.15 (18)	C39—C34—C35—C36	−1.09 (18)
C13—C14—C15—C16	177.48 (12)	C33—C34—C35—C36	176.43 (12)
C14—C15—C16—C17	−2.1 (2)	C34—C35—C36—C37	−1.59 (19)
C15—C16—C17—C18	2.8 (2)	C35—C36—C37—C38	2.0 (2)
C16—C17—C18—C19	0.78 (18)	C36—C37—C38—C39	0.35 (18)
C15—C14—C19—C18	5.64 (17)	C37—C38—C39—C34	−2.96 (17)
C13—C14—C19—C18	−174.04 (10)	C37—C38—C39—C31	−175.54 (11)
C15—C14—C19—C11	−176.37 (10)	C35—C34—C39—C38	3.36 (17)
C13—C14—C19—C11	3.94 (13)	C33—C34—C39—C38	−174.55 (10)
C17—C18—C19—C14	−4.91 (17)	C35—C34—C39—C31	177.44 (10)
C17—C18—C19—C11	177.62 (11)	C33—C34—C39—C31	−0.47 (13)
C1—C11—C19—C14	160.31 (12)	C21—C31—C39—C38	−19.8 (2)
C12—C11—C19—C14	−15.02 (13)	C32—C31—C39—C38	159.10 (12)
C1—C11—C19—C18	−22.0 (2)	C21—C31—C39—C34	167.16 (13)
C12—C11—C19—C18	162.64 (12)	C32—C31—C39—C34	−13.99 (12)