N-(p-Chloro­phenyl)-3,3-di­phenyl-4-([beta]-phenyl­styryl)azetidin-2-one

In the title compound, C₃₅H₂₆ClNO, the four-membered [beta]-lactam ring is essentially planar, with a maximum deviation of 0.012 (1) Å for the N atom. The C-C bond lengths in the [beta]-lactam ring are 1.591 (2) and 1.549 (2) Å. The two phenyl rings attached to the [beta]-lactam ring are nearly perpendicular to each other [83.2 (1)°].

S1. Comment

Since the structure and conformation of β-lactams play a key role in the biological activity of β-lactam antibiotics, it is worthwhile studying their activity when modified by substituents. The activity and selectivity of the 4-substituted 2-azetidinone ring can be decisively influenced by the subtituents attached to the β-lactam ring (Kumar et al., 1993; Sharma et al., 1994; Manhas et al., 1988). Previously, some structural studies were made by changing the subtituents around the β-lactam ring (Ercan et al. 1996a,b; Kabak et al., 1999a,b).

The four-membered β-lactam ring of (I) is nearly planar, with a slight deviation of the N1 atom [0.012 (1) Å]. The bond lengths on the lactam ring are comparable with those in monocyclic 3- or 4-substituted 2-azetidinones (Kabak et al., 1999a,b, and references therein). Due to the different substituents attached to the β-lactam ring, a very significant elongation of the C8—C21 bond [1.591 (2) Å] is observed in this compound which is different from the previous works (Table 2). This may be due to the substituents at the C8 and C21 atoms. The diagonal contact distances deviate much from those observed in similar works (Table 2). The valence angles at the β-lactam ring deviate from 90° by 2–6°, producing a trapezoid rather than a rectangular shape for the ring.

The angle between two phenyl rings which are attached to the C8 atom shows that these two substituents are nearly perpendicular to each other [83.2 (1)°] and the corresponding torsion angle (C9—C8—C15—C16) is 69.2 (2)°. The other two phenyl groups in the phenylstyryl group, which are attached to the β-lactam ring via the C23 and C22 atoms to the C21 atom, are close to being perpendicular [88.8 (1)°].

There are no notable intermolecular interactions.

S2. Experimental

A solution of diphenylacetyl chloride (0.002 mol, 1.92 ml) in dry benzene (20 ml) was added dropwise over 1 h at room temperature to a mixture of β-phenylcinnamaldehyde N-p-chlorophenylimine (0.001 mol, 0.242 g) and triethylamine (0.002 mol, 2.78 ml) in dry benzene. The mixture was stirred for 2 h at room temperature and the amine salt removed by filtration of the mixture. The filtrate was then washed with 5% HCl and water, and dried over sodium sulfate. The title compound was crystallized from ethanol.

S3. Refinement

H atoms were placed geometrically on the corresponding C atoms. Because of the large displacement parameters of the C10 and C11 atoms, the C9–C14 benzene ring was restrained during the refinement process.

Computing details

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1994); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1990).

(I)

Crystal data

C35H26ClNO	F(000) = 1072
Mr = 512.02	Dx = 1.231 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71069 Å
a = 14.0672 (13) Å	Cell parameters from 25 reflections
b = 12.692 (1) Å	θ = 20.1–27.9°
c = 15.5238 (17) Å	µ = 0.17 mm^−1
β = 92.972 (9)°	T = 293 K
V = 2767.9 (5) Å^3	Prism, white
Z = 4	0.85 × 0.55 × 0.35 mm

Data collection

Rigaku AFC-7S diffractometer	4115 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.031
Graphite monochromator	θmax = 30.0°, θmin = 2.0°
ω–2θ scans	h = 0→19
Absorption correction: ψ scans (north et al., 1968) ?	k = 0→17
Tmin = 0.866, Tmax = 0.944	l = −21→21
8362 measured reflections	3 standard reflections every 150 reflections
8067 independent reflections	intensity decay: 0.6%

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.165	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.074P)^2 + 0.4079P] where P = (Fo^2 + 2Fc^2)/3
8067 reflections	(Δ/σ)max < 0.001
362 parameters	Δρmax = 0.24 e Å^−3
19 restraints	Δρmin = −0.35 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	Occ. (<1)
Cl1	0.21711 (6)	−0.54828 (4)	0.08541 (5)	0.0921 (2)
O1	0.23169 (12)	−0.00232 (11)	0.17684 (8)	0.0659 (4)
N1	0.25368 (10)	−0.08797 (11)	0.04540 (8)	0.0443 (3)
C1	0.24103 (14)	−0.24208 (15)	0.13719 (10)	0.0518 (4)
H1	0.2440	−0.1991	0.1858	0.062*
C2	0.23200 (15)	−0.34996 (16)	0.14577 (12)	0.0563 (5)
H2	0.2290	−0.3798	0.2003	0.068*
C3	0.22751 (13)	−0.41295 (14)	0.07405 (12)	0.0530 (4)
C4	0.23218 (14)	−0.37034 (15)	−0.00697 (12)	0.0555 (5)
H4	0.2287	−0.4137	−0.0553	0.067*
C5	0.24207 (13)	−0.26229 (15)	−0.01622 (10)	0.0475 (4)
H5	0.2463	−0.2331	−0.0708	0.057*
C6	0.24560 (11)	−0.19807 (13)	0.05541 (10)	0.0399 (3)
C7	0.24586 (13)	−0.00521 (14)	0.10099 (11)	0.0466 (4)
C8	0.26382 (11)	0.07733 (13)	0.03019 (10)	0.0422 (4)
C9	0.17884 (12)	0.14599 (14)	0.00520 (11)	0.0469 (4)
C10	0.0957 (6)	0.1462 (7)	0.0569 (7)	0.0650 (18)	0.57 (3)
H10	0.0932	0.1036	0.1055	0.078*	0.57
C11	0.0208 (6)	0.2111 (8)	0.0322 (8)	0.083 (2)	0.57 (3)
H11	−0.0310	0.2176	0.0667	0.099*	0.57
C10'	0.0904 (9)	0.1231 (17)	0.0244 (18)	0.090 (5)	0.43 (3)
H10'	0.0809	0.0666	0.0612	0.108*	0.43
C11'	0.0118 (8)	0.178 (2)	−0.007 (2)	0.111 (8)	0.43 (3)
H11'	−0.0490	0.1524	0.0002	0.134*	0.43
C12	0.02316 (17)	0.2691 (3)	−0.0479 (2)	0.1031 (10)
H12	−0.0320	0.2994	−0.0725	0.124*
C13	0.10695 (16)	0.2788 (2)	−0.08677 (16)	0.0749 (6)
H13	0.1120	0.3260	−0.1321	0.090*
C14	0.18458 (14)	0.21898 (16)	−0.05942 (13)	0.0592 (5)
H14	0.2421	0.2284	−0.0854	0.071*
C15	0.35263 (12)	0.14223 (13)	0.05076 (11)	0.0451 (4)
C16	0.35612 (15)	0.20333 (16)	0.12497 (13)	0.0607 (5)
H16	0.3049	0.2027	0.1606	0.073*
C17	0.4346 (2)	0.26511 (18)	0.14673 (16)	0.0768 (7)
H17	0.4363	0.3045	0.1973	0.092*
C18	0.50944 (17)	0.26865 (18)	0.09437 (18)	0.0759 (7)
H18	0.5618	0.3110	0.1088	0.091*
C19	0.50711 (14)	0.20960 (18)	0.02067 (17)	0.0694 (6)
H19	0.5583	0.2120	−0.0149	0.083*
C20	0.42904 (13)	0.14588 (16)	−0.00184 (13)	0.0557 (4)
H20	0.4283	0.1059	−0.0521	0.067*
C21	0.27534 (12)	−0.02258 (13)	−0.03024 (10)	0.0425 (4)
H21	0.3412	−0.0318	−0.0465	0.051*
C22	0.20596 (12)	−0.03453 (14)	−0.10572 (10)	0.0455 (4)
H22	0.1461	−0.0607	−0.0944	0.055*
C23	0.22115 (12)	−0.01142 (13)	−0.18790 (10)	0.0421 (4)
C24	0.31431 (12)	0.02977 (13)	−0.21515 (10)	0.0436 (4)
C25	0.39607 (15)	−0.03146 (17)	−0.21180 (13)	0.0608 (5)
H25	0.3932	−0.1013	−0.1939	0.073*
C26	0.48231 (17)	0.0105 (3)	−0.23497 (17)	0.0827 (7)
H26	0.5367	−0.0311	−0.2326	0.099*
C27	0.48721 (18)	0.1138 (3)	−0.26141 (18)	0.0904 (8)
H27	0.5450	0.1418	−0.2769	0.109*
C28	0.40756 (19)	0.1752 (2)	−0.26501 (16)	0.0778 (7)
H28	0.4114	0.2453	−0.2819	0.093*
C29	0.32091 (14)	0.13326 (16)	−0.24350 (13)	0.0575 (5)
H29	0.2665	0.1749	−0.2481	0.069*
C30	0.14310 (12)	−0.02462 (13)	−0.25553 (10)	0.0425 (4)
C31	0.16342 (13)	−0.05656 (15)	−0.33841 (11)	0.0489 (4)
H31	0.2264	−0.0645	−0.3526	0.059*
C32	0.09065 (15)	−0.07671 (17)	−0.40000 (12)	0.0608 (5)
H32	0.1051	−0.0990	−0.4549	0.073*
C33	−0.00214 (15)	−0.06388 (18)	−0.38022 (14)	0.0655 (5)
H33	−0.0507	−0.0777	−0.4217	0.079*
C34	−0.02423 (14)	−0.03063 (17)	−0.29915 (14)	0.0616 (5)
H34	−0.0875	−0.0223	−0.2859	0.074*
C35	0.04763 (14)	−0.00968 (15)	−0.23754 (12)	0.0530 (4)
H35	0.0324	0.0146	−0.1835	0.064*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.1336 (6)	0.0431 (3)	0.1007 (5)	−0.0021 (3)	0.0165 (4)	0.0019 (3)
O1	0.1041 (11)	0.0546 (8)	0.0405 (7)	−0.0051 (8)	0.0195 (7)	−0.0026 (6)
N1	0.0576 (8)	0.0429 (7)	0.0326 (6)	−0.0007 (6)	0.0063 (6)	0.0041 (6)
C1	0.0706 (12)	0.0472 (9)	0.0379 (8)	0.0013 (9)	0.0044 (8)	0.0015 (7)
C2	0.0727 (12)	0.0494 (10)	0.0474 (9)	0.0026 (9)	0.0078 (9)	0.0089 (8)
C3	0.0545 (10)	0.0406 (9)	0.0643 (11)	0.0034 (8)	0.0072 (9)	0.0008 (8)
C4	0.0649 (12)	0.0504 (10)	0.0517 (10)	0.0070 (9)	0.0068 (8)	−0.0089 (8)
C5	0.0541 (10)	0.0501 (10)	0.0390 (8)	0.0047 (8)	0.0077 (7)	0.0003 (7)
C6	0.0395 (8)	0.0416 (8)	0.0388 (8)	0.0020 (7)	0.0030 (6)	0.0024 (6)
C7	0.0549 (10)	0.0451 (9)	0.0402 (9)	−0.0010 (8)	0.0065 (7)	−0.0004 (7)
C8	0.0445 (8)	0.0431 (8)	0.0396 (8)	−0.0016 (7)	0.0062 (6)	0.0023 (7)
C9	0.0411 (9)	0.0457 (9)	0.0544 (10)	−0.0007 (7)	0.0059 (7)	0.0015 (8)
C10	0.050 (2)	0.084 (3)	0.063 (4)	0.003 (2)	0.025 (3)	0.005 (3)
C11	0.052 (3)	0.098 (4)	0.101 (5)	0.010 (3)	0.024 (3)	−0.005 (4)
C10'	0.064 (5)	0.104 (9)	0.106 (11)	0.025 (5)	0.043 (6)	0.058 (8)
C11'	0.039 (4)	0.132 (12)	0.167 (16)	0.018 (5)	0.034 (6)	0.069 (11)
C12	0.0475 (13)	0.101 (2)	0.160 (3)	0.0158 (13)	−0.0029 (15)	0.037 (2)
C13	0.0623 (13)	0.0728 (14)	0.0891 (16)	0.0092 (11)	−0.0023 (11)	0.0230 (13)
C14	0.0503 (10)	0.0598 (11)	0.0680 (12)	0.0057 (9)	0.0083 (9)	0.0141 (10)
C15	0.0441 (9)	0.0414 (8)	0.0493 (9)	0.0011 (7)	−0.0011 (7)	0.0067 (7)
C16	0.0701 (13)	0.0509 (10)	0.0611 (11)	−0.0073 (9)	0.0045 (10)	−0.0051 (9)
C17	0.0912 (17)	0.0563 (13)	0.0807 (15)	−0.0135 (12)	−0.0154 (13)	−0.0067 (11)
C18	0.0609 (13)	0.0575 (13)	0.1062 (19)	−0.0118 (11)	−0.0242 (13)	0.0105 (13)
C19	0.0442 (10)	0.0634 (13)	0.1002 (17)	−0.0015 (9)	−0.0010 (11)	0.0158 (13)
C20	0.0446 (9)	0.0569 (11)	0.0658 (11)	0.0000 (8)	0.0039 (8)	0.0037 (9)
C21	0.0467 (9)	0.0459 (9)	0.0354 (7)	−0.0008 (7)	0.0073 (6)	0.0036 (7)
C22	0.0476 (9)	0.0482 (9)	0.0410 (8)	−0.0074 (7)	0.0046 (7)	0.0047 (7)
C23	0.0485 (9)	0.0393 (8)	0.0387 (8)	0.0004 (7)	0.0049 (6)	0.0027 (6)
C24	0.0483 (9)	0.0492 (9)	0.0337 (7)	−0.0004 (7)	0.0057 (6)	0.0024 (7)
C25	0.0608 (12)	0.0674 (13)	0.0552 (11)	0.0138 (10)	0.0115 (9)	0.0060 (10)
C26	0.0537 (12)	0.115 (2)	0.0805 (16)	0.0194 (14)	0.0141 (11)	0.0049 (15)
C27	0.0605 (14)	0.120 (2)	0.0926 (18)	−0.0210 (15)	0.0231 (12)	0.0044 (17)
C28	0.0819 (16)	0.0694 (14)	0.0840 (16)	−0.0208 (12)	0.0226 (13)	0.0095 (12)
C29	0.0599 (11)	0.0531 (11)	0.0605 (11)	−0.0017 (9)	0.0119 (9)	0.0079 (9)
C30	0.0495 (9)	0.0394 (8)	0.0388 (8)	−0.0013 (7)	0.0029 (7)	0.0058 (7)
C31	0.0526 (10)	0.0515 (10)	0.0427 (9)	−0.0035 (8)	0.0043 (7)	0.0010 (7)
C32	0.0685 (12)	0.0686 (13)	0.0448 (9)	−0.0080 (10)	−0.0005 (9)	−0.0054 (9)
C33	0.0604 (12)	0.0725 (14)	0.0620 (12)	−0.0057 (10)	−0.0128 (9)	−0.0020 (10)
C34	0.0482 (10)	0.0678 (13)	0.0686 (13)	0.0025 (9)	0.0000 (9)	0.0046 (10)
C35	0.0552 (10)	0.0567 (11)	0.0477 (10)	0.0055 (9)	0.0069 (8)	0.0030 (8)

Geometric parameters (Å, º)

Cl1—C3	1.7335 (19)	C13—C14	1.379 (3)
O1—C7	1.205 (2)	C15—C20	1.384 (2)
N1—C7	1.367 (2)	C15—C16	1.387 (3)
N1—C6	1.411 (2)	C16—C17	1.381 (3)
N1—C21	1.482 (2)	C17—C18	1.364 (4)
C1—C2	1.382 (3)	C18—C19	1.367 (3)
C1—C6	1.392 (2)	C19—C20	1.394 (3)
C2—C3	1.370 (3)	C21—C22	1.493 (2)
C3—C4	1.374 (3)	C22—C23	1.337 (2)
C4—C5	1.387 (3)	C23—C30	1.489 (2)
C5—C6	1.377 (2)	C23—C24	1.492 (2)
C7—C8	1.549 (2)	C24—C25	1.387 (3)
C8—C9	1.514 (2)	C24—C29	1.390 (2)
C8—C15	1.517 (2)	C25—C26	1.389 (3)
C8—C21	1.591 (2)	C26—C27	1.377 (4)
C9—C10'	1.327 (12)	C27—C28	1.363 (4)
C9—C14	1.371 (3)	C28—C29	1.387 (3)
C9—C10	1.452 (9)	C30—C31	1.393 (2)
C10—C11	1.377 (9)	C30—C35	1.399 (2)
C11—C12	1.447 (12)	C31—C32	1.388 (3)
C10'—C11'	1.379 (10)	C32—C33	1.366 (3)
C11'—C12	1.327 (13)	C33—C34	1.378 (3)
C12—C13	1.357 (4)	C34—C35	1.381 (3)
C7—N1—C6	132.96 (14)	C13—C12—C11	119.2 (4)
C7—N1—C21	95.54 (13)	C12—C13—C14	120.4 (2)
C6—N1—C21	131.50 (13)	C9—C14—C13	121.43 (19)
C2—C1—C6	119.63 (16)	C20—C15—C16	118.43 (17)
C3—C2—C1	120.04 (17)	C20—C15—C8	123.40 (16)
C2—C3—C4	120.80 (18)	C16—C15—C8	118.14 (15)
C2—C3—Cl1	119.75 (15)	C17—C16—C15	120.9 (2)
C4—C3—Cl1	119.44 (15)	C18—C17—C16	120.3 (2)
C3—C4—C5	119.61 (17)	C17—C18—C19	119.7 (2)
C6—C5—C4	120.08 (16)	C18—C19—C20	120.8 (2)
C5—C6—C1	119.84 (16)	C15—C20—C19	119.8 (2)
C5—C6—N1	119.79 (14)	N1—C21—C22	114.32 (13)
C1—C6—N1	120.38 (15)	N1—C21—C8	87.00 (11)
O1—C7—N1	131.52 (16)	C22—C21—C8	117.47 (14)
O1—C7—C8	135.59 (16)	C23—C22—C21	126.59 (15)
N1—C7—C8	92.88 (12)	C22—C23—C30	119.98 (15)
C9—C8—C15	111.86 (14)	C22—C23—C24	122.24 (15)
C9—C8—C7	114.56 (13)	C30—C23—C24	117.77 (13)
C15—C8—C7	112.39 (14)	C25—C24—C29	118.20 (17)
C9—C8—C21	114.27 (14)	C25—C24—C23	122.13 (16)
C15—C8—C21	116.69 (13)	C29—C24—C23	119.66 (16)
C7—C8—C21	84.53 (12)	C24—C25—C26	120.6 (2)
C10'—C9—C14	113.9 (6)	C27—C26—C25	120.0 (2)
C10'—C9—C10	23.7 (12)	C28—C27—C26	120.2 (2)
C14—C9—C10	118.9 (4)	C27—C28—C29	120.1 (2)
C10'—C9—C8	123.6 (5)	C28—C29—C24	120.9 (2)
C14—C9—C8	120.06 (15)	C31—C30—C35	117.98 (16)
C10—C9—C8	120.5 (4)	C31—C30—C23	120.33 (15)
C11—C10—C9	118.3 (7)	C35—C30—C23	121.65 (15)
C10—C11—C12	119.5 (6)	C32—C31—C30	120.71 (17)
C9—C10'—C11'	123.5 (9)	C33—C32—C31	120.16 (18)
C12—C11'—C10'	119.8 (9)	C32—C33—C34	120.34 (18)
C11'—C12—C13	114.8 (7)	C33—C34—C35	119.99 (18)
C11'—C12—C11	30.7 (15)	C34—C35—C30	120.77 (17)
C6—C1—C2—C3	−0.1 (3)	C7—C8—C15—C20	120.52 (18)
C1—C2—C3—C4	0.2 (3)	C21—C8—C15—C20	25.3 (2)
C1—C2—C3—Cl1	179.50 (16)	C9—C8—C15—C16	69.2 (2)
C2—C3—C4—C5	0.3 (3)	C7—C8—C15—C16	−61.4 (2)
Cl1—C3—C4—C5	−178.95 (15)	C21—C8—C15—C16	−156.62 (16)
C3—C4—C5—C6	−1.1 (3)	C20—C15—C16—C17	−1.0 (3)
C4—C5—C6—C1	1.2 (3)	C8—C15—C16—C17	−179.25 (19)
C4—C5—C6—N1	−178.68 (17)	C15—C16—C17—C18	1.3 (3)
C2—C1—C6—C5	−0.7 (3)	C16—C17—C18—C19	−0.9 (4)
C2—C1—C6—N1	179.24 (17)	C17—C18—C19—C20	0.1 (3)
C7—N1—C6—C5	169.59 (18)	C16—C15—C20—C19	0.3 (3)
C21—N1—C6—C5	−11.5 (3)	C8—C15—C20—C19	178.42 (18)
C7—N1—C6—C1	−10.3 (3)	C18—C19—C20—C15	0.1 (3)
C21—N1—C6—C1	168.61 (16)	C7—N1—C21—C22	−120.68 (15)
C6—N1—C7—O1	2.0 (3)	C6—N1—C21—C22	60.1 (2)
C21—N1—C7—O1	−177.2 (2)	C7—N1—C21—C8	−1.78 (13)
C6—N1—C7—C8	−178.98 (17)	C6—N1—C21—C8	179.01 (17)
C21—N1—C7—C8	1.83 (13)	C9—C8—C21—N1	−112.94 (14)
O1—C7—C8—C9	−68.6 (3)	C15—C8—C21—N1	113.92 (14)
N1—C7—C8—C9	112.51 (15)	C7—C8—C21—N1	1.58 (11)
O1—C7—C8—C15	60.6 (3)	C9—C8—C21—C22	3.0 (2)
N1—C7—C8—C15	−118.36 (15)	C15—C8—C21—C22	−130.14 (15)
O1—C7—C8—C21	177.2 (2)	C7—C8—C21—C22	117.52 (15)
N1—C7—C8—C21	−1.71 (12)	N1—C21—C22—C23	−158.94 (17)
C15—C8—C9—C10'	−145.6 (17)	C8—C21—C22—C23	101.3 (2)
C7—C8—C9—C10'	−16.2 (17)	C21—C22—C23—C30	−177.98 (16)
C21—C8—C9—C10'	79.1 (17)	C21—C22—C23—C24	0.8 (3)
C15—C8—C9—C14	53.4 (2)	C22—C23—C24—C25	67.9 (2)
C7—C8—C9—C14	−177.19 (17)	C30—C23—C24—C25	−113.23 (19)
C21—C8—C9—C14	−82.0 (2)	C22—C23—C24—C29	−110.9 (2)
C15—C8—C9—C10	−117.7 (5)	C30—C23—C24—C29	68.0 (2)
C7—C8—C9—C10	11.7 (5)	C29—C24—C25—C26	1.0 (3)
C21—C8—C9—C10	106.9 (5)	C23—C24—C25—C26	−177.84 (19)
C10'—C9—C10—C11	−76.0 (19)	C24—C25—C26—C27	0.1 (4)
C14—C9—C10—C11	7.9 (7)	C25—C26—C27—C28	0.0 (4)
C8—C9—C10—C11	179.1 (5)	C26—C27—C28—C29	−1.1 (4)
C9—C10—C11—C12	5.6 (9)	C27—C28—C29—C24	2.3 (4)
C14—C9—C10'—C11'	−9.7 (14)	C25—C24—C29—C28	−2.2 (3)
C10—C9—C10'—C11'	98 (2)	C23—C24—C29—C28	176.68 (19)
C8—C9—C10'—C11'	−171.8 (8)	C22—C23—C30—C31	−145.48 (17)
C9—C10'—C11'—C12	−11.0 (16)	C24—C23—C30—C31	35.7 (2)
C10'—C11'—C12—C13	27 (2)	C22—C23—C30—C35	32.0 (2)
C10'—C11'—C12—C11	−79.2 (19)	C24—C23—C30—C35	−146.90 (17)
C10—C11—C12—C11'	74.5 (12)	C35—C30—C31—C32	−2.4 (3)
C10—C11—C12—C13	−15.5 (10)	C23—C30—C31—C32	175.13 (17)
C11'—C12—C13—C14	−23 (2)	C30—C31—C32—C33	0.9 (3)
C11—C12—C13—C14	11.6 (7)	C31—C32—C33—C34	0.2 (3)
C10'—C9—C14—C13	13.7 (16)	C32—C33—C34—C35	0.3 (3)
C10—C9—C14—C13	−12.2 (5)	C33—C34—C35—C30	−1.8 (3)
C8—C9—C14—C13	176.5 (2)	C31—C30—C35—C34	2.8 (3)
C12—C13—C14—C9	2.3 (4)	C23—C30—C35—C34	−174.66 (17)
C9—C8—C15—C20	−108.96 (19)