4',5a'-Di­phenyl-10-oxo­spiro­[phenanthrene­[9,2']­oxeto­[5,4-b]­oxazole]

In the title compound, C₂₉H₁₉NO₃, the phenanthrene is out of planarity with its di­hydro­benzene ring being distorted towards a half-chair conformation. The relative configuration of the planar oxetane and oxazole rings is conditioned by the Csp³ state of the shared atoms.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.042
• wR factor = 0.117
• Data-to-parameter ratio = 11.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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S1. Comment

In our ongoing research on the photocycloaddition reactions of α-dicarbonyl compounds with oxazole derivatives (Zhang et al., 2003), we have carried out the photoreactions of 9,10-phenanthrenedione with 2,5-diphenyloxazole and isolated the title compound, (I). We have also structurally analysed (I) and the results are presented here.

The bond lengths and angles in (I) (Fig. 1) are within normal ranges (Allen et al., 1987). Those within the spiroxetane–oxazole system (C1/C16/O2/C3/O1,/2/N1) are comparable to the corresponding values in the related structure, spiro[indole-3,2'-(2'aH,5'aH)oxeto[5,4-b]oxazol]-2(1H)-one derivatives (Usman et al., 2003). Similar to these related structures are the elongation of Csp³—Csp³ for the C1–C16 moiety and the planarity of the spiroxetane ring. The dihedral angle between the O2/C3/C1 and O2/C1/C16 planes is 177.0 (1)° [176.9 (3)–178.6 (2)°; Usman et al., 2003].

The planes through the oxetane and oxazole rings make a dihedral angle of 113.4 (1)°. This is conditioned by the eclipsed configuration of the sp³ state of the shared atoms C1 and C3. The relative configurations of the phenyl rings C4–C9 and C10–C15 with respect to the oxetane-oxazole system are determined by their attached atoms C3 (sp³) and C2 (sp²), respectively. The two phenyl rings make dihedral angles of 68.1 (1) and 22.4 (1)°, respectively, with the oxazole.

The phenanthrene is out of planarity with its dihydrobenzene ring (C16–C18/C23/C24/C29) having a half-chair conformation. Atoms C16 and C17 by 0.209 (2) and 0.374 (2) Å in opposite directions from the C18/C23/C24/C29 plane. This plane makes dihedral angles of 11.8 (1) and 8.0 (1)° with the fused benzene rings C18–C23 and C24–C29, respectively. The dihydrobenzene mean plane is nearly orthogonal to the oxetane ring with a dihedral angle of 82.2 (1)°. This is conditioned by the sp³ state of the shared atom C16. Ketone atom O3 attached to the C17 deviates by 0.715 (2) Å from the dihydrobenzene mean plane.

S2. Experimental

The title compound was separated by column chromatography on silica gel with petroleum ether–ethyl acetate as eluants. Single crystals suitable for X-ray diffraction measurement were obtained from slow evaporation of a petroleum ether–acetone solution.

S3. Refinement

All H atoms were located from difference Fourier maps and refined isotropically [C—H = 0.92 (2)–1.02 (2) Å]. Owing to large fraction of weak data at higher angles, the 2θ maximum was limited to 52°. The maximum and minimum electron-density peaks are located 0.98 Å from O3 and 1.29 Å from C6, respectively.

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT and SADABS (Sheldrick, 1996); program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Figures

Fig. 1. The structure of the compound (I), showing 50% probability displacement ellipsoids and the atom-numbering scheme.

4',5a'-Diphenyl-10-oxospiro[phenanthrene[9,2']oxeto[5,4-b]oxazole]

Crystal data

C29H19NO3	F(000) = 448
Mr = 429.45	Dx = 1.324 Mg m^−3
Triclinic, P1	Melting point: 466(1) K
a = 8.3475 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.8671 (6) Å	Cell parameters from 4070 reflections
c = 11.9106 (6) Å	θ = 2.6–28.3°
α = 74.148 (1)°	µ = 0.09 mm^−1
β = 89.736 (1)°	T = 293 K
γ = 72.344 (1)°	Block, yellow
V = 1077.59 (9) Å^3	0.50 × 0.40 × 0.30 mm
Z = 2

Data collection

Siemens SMART CCD area-detector diffractometer	3482 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.016
Graphite monochromator	θmax = 26.0°, θmin = 2.6°
Detector resolution: 8.33 pixels mm^-1	h = −10→7
ω scans	k = −14→14
5771 measured reflections	l = −13→14
4110 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) = 0.117	All H-atom parameters refined
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0554P)^2 + 0.1949P] where P = (Fo^2 + 2Fc^2)/3
4110 reflections	(Δ/σ)max < 0.001
374 parameters	Δρmax = 0.20 e Å^−3
0 restraints	Δρmin = −0.19 e Å^−3

Special details

Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different ϕ angle (0, 88 and 180°) for the crystal and each exposure of 30 s covered 0.3° in ω. The crystal-to-detector distance was 5 cm and the detector swing angle was −35°. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the intensity of duplicate reflections, and was found to be negligible.

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
O1	1.08581 (13)	0.64435 (8)	0.98562 (8)	0.0474 (3)
O2	0.90521 (13)	0.66549 (9)	0.82385 (9)	0.0516 (3)
O3	0.85720 (19)	0.78044 (15)	0.58936 (11)	0.0969 (5)
N1	0.97931 (14)	0.85379 (10)	0.93414 (10)	0.0432 (3)
C1	0.98666 (17)	0.81986 (13)	0.82579 (12)	0.0426 (3)
C2	1.03276 (16)	0.75302 (12)	1.01582 (11)	0.0405 (3)
C3	1.06025 (17)	0.67794 (12)	0.85985 (11)	0.0430 (3)
C4	1.21255 (18)	0.60787 (12)	0.81193 (12)	0.0454 (3)
C5	1.3727 (2)	0.59056 (17)	0.85888 (15)	0.0631 (4)
C6	1.5136 (2)	0.5288 (2)	0.81309 (18)	0.0765 (6)
C7	1.4954 (3)	0.48210 (18)	0.72151 (17)	0.0731 (5)
C8	1.3372 (2)	0.50072 (17)	0.67356 (16)	0.0666 (5)
C9	1.1951 (2)	0.56434 (14)	0.71752 (14)	0.0535 (4)
C10	1.04697 (16)	0.73900 (13)	1.14238 (12)	0.0425 (3)
C11	1.0550 (2)	0.83739 (15)	1.18159 (14)	0.0529 (4)
C12	1.0688 (2)	0.82331 (18)	1.30035 (15)	0.0644 (4)
C13	1.0712 (2)	0.71390 (19)	1.37997 (15)	0.0665 (5)
C14	1.0635 (3)	0.61655 (19)	1.34128 (15)	0.0690 (5)
C15	1.0529 (2)	0.62783 (16)	1.22244 (14)	0.0570 (4)
C16	0.82167 (18)	0.79788 (14)	0.78354 (12)	0.0469 (3)
C17	0.79287 (19)	0.84497 (17)	0.65087 (14)	0.0587 (4)
C18	0.69292 (19)	0.97626 (16)	0.60449 (13)	0.0563 (4)
C19	0.7150 (3)	1.0433 (2)	0.49258 (16)	0.0713 (5)
C20	0.6258 (3)	1.1661 (2)	0.4495 (2)	0.0845 (6)
C21	0.5138 (3)	1.2228 (2)	0.5172 (2)	0.0870 (6)
C22	0.4880 (3)	1.15793 (19)	0.62716 (19)	0.0745 (5)
C23	0.57677 (19)	1.03246 (15)	0.67361 (14)	0.0551 (4)
C24	0.54650 (18)	0.95677 (15)	0.78832 (14)	0.0532 (4)
C25	0.4010 (2)	0.9967 (2)	0.84388 (18)	0.0679 (5)
C26	0.3734 (3)	0.9247 (2)	0.9491 (2)	0.0780 (6)
C27	0.4883 (3)	0.8113 (2)	1.00138 (18)	0.0732 (5)
C28	0.6343 (2)	0.76805 (18)	0.94782 (15)	0.0604 (4)
C29	0.66309 (18)	0.84068 (15)	0.84179 (13)	0.0494 (3)
H1	1.0359 (18)	0.8693 (13)	0.7644 (13)	0.041 (4)*
H5	1.386 (2)	0.6223 (17)	0.9221 (17)	0.075 (5)*
H6	1.625 (3)	0.520 (2)	0.8462 (19)	0.092 (7)*
H7	1.589 (3)	0.4390 (19)	0.6928 (18)	0.082 (6)*
H8	1.324 (3)	0.4689 (18)	0.6075 (19)	0.082 (6)*
H9	1.081 (2)	0.5797 (16)	0.6823 (16)	0.069 (5)*
H11	1.050 (2)	0.9136 (17)	1.1238 (16)	0.065 (5)*
H12	1.073 (2)	0.8896 (18)	1.3272 (17)	0.076 (6)*
H13	1.079 (2)	0.7062 (17)	1.4609 (18)	0.077 (6)*
H14	1.071 (3)	0.534 (2)	1.4001 (19)	0.088 (6)*
H15	1.049 (2)	0.5582 (18)	1.1932 (17)	0.073 (5)*
H19	0.790 (2)	0.9980 (18)	0.4487 (17)	0.073 (6)*
H20	0.642 (3)	1.211 (2)	0.372 (2)	0.108 (8)*
H21	0.452 (3)	1.312 (2)	0.485 (2)	0.110 (8)*
H22	0.403 (3)	1.199 (2)	0.672 (2)	0.094 (7)*
H25	0.316 (3)	1.078 (2)	0.8064 (19)	0.089 (6)*
H26	0.275 (3)	0.953 (2)	0.9878 (19)	0.090 (6)*
H27	0.472 (3)	0.759 (2)	1.075 (2)	0.090 (7)*
H28	0.715 (2)	0.6907 (17)	0.9787 (15)	0.059 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0659 (6)	0.0389 (5)	0.0360 (5)	−0.0129 (4)	0.0062 (4)	−0.0122 (4)
O2	0.0535 (6)	0.0510 (6)	0.0561 (6)	−0.0175 (5)	0.0062 (5)	−0.0235 (5)
O3	0.0951 (10)	0.1126 (11)	0.0513 (7)	0.0254 (8)	−0.0011 (7)	−0.0376 (7)
N1	0.0474 (6)	0.0415 (6)	0.0423 (6)	−0.0140 (5)	0.0048 (5)	−0.0145 (5)
C1	0.0445 (7)	0.0424 (7)	0.0387 (7)	−0.0115 (6)	0.0056 (5)	−0.0101 (6)
C2	0.0422 (7)	0.0414 (7)	0.0423 (7)	−0.0156 (6)	0.0082 (5)	−0.0162 (6)
C3	0.0499 (7)	0.0434 (7)	0.0357 (7)	−0.0136 (6)	0.0037 (5)	−0.0125 (5)
C4	0.0536 (8)	0.0383 (7)	0.0389 (7)	−0.0079 (6)	0.0041 (6)	−0.0098 (5)
C5	0.0570 (9)	0.0701 (11)	0.0548 (9)	−0.0014 (8)	−0.0040 (7)	−0.0266 (8)
C6	0.0527 (10)	0.0897 (14)	0.0727 (12)	0.0038 (9)	−0.0028 (9)	−0.0292 (10)
C7	0.0657 (11)	0.0695 (11)	0.0676 (11)	0.0067 (9)	0.0143 (9)	−0.0248 (9)
C8	0.0775 (12)	0.0648 (11)	0.0578 (10)	−0.0115 (9)	0.0136 (9)	−0.0302 (8)
C9	0.0613 (9)	0.0534 (9)	0.0485 (8)	−0.0156 (7)	0.0091 (7)	−0.0218 (7)
C10	0.0408 (7)	0.0498 (8)	0.0404 (7)	−0.0153 (6)	0.0081 (5)	−0.0174 (6)
C11	0.0586 (9)	0.0521 (9)	0.0510 (8)	−0.0151 (7)	0.0053 (7)	−0.0222 (7)
C12	0.0736 (11)	0.0702 (11)	0.0571 (10)	−0.0171 (9)	0.0050 (8)	−0.0365 (9)
C13	0.0696 (11)	0.0920 (14)	0.0418 (8)	−0.0213 (9)	0.0116 (7)	−0.0298 (9)
C14	0.0891 (13)	0.0810 (13)	0.0429 (9)	−0.0386 (10)	0.0156 (8)	−0.0140 (8)
C15	0.0745 (11)	0.0620 (10)	0.0442 (8)	−0.0333 (8)	0.0120 (7)	−0.0177 (7)
C16	0.0457 (7)	0.0525 (8)	0.0440 (7)	−0.0127 (6)	0.0043 (6)	−0.0191 (6)
C17	0.0457 (8)	0.0797 (11)	0.0469 (8)	−0.0067 (8)	0.0024 (6)	−0.0264 (8)
C18	0.0481 (8)	0.0724 (10)	0.0476 (8)	−0.0153 (7)	−0.0027 (6)	−0.0196 (7)
C19	0.0682 (11)	0.0910 (14)	0.0502 (9)	−0.0203 (10)	0.0012 (8)	−0.0183 (9)
C20	0.0982 (16)	0.0856 (15)	0.0619 (12)	−0.0316 (13)	−0.0036 (11)	−0.0053 (11)
C21	0.0973 (16)	0.0685 (13)	0.0815 (15)	−0.0177 (12)	−0.0035 (12)	−0.0084 (11)
C22	0.0709 (12)	0.0674 (12)	0.0811 (13)	−0.0126 (9)	0.0052 (10)	−0.0247 (10)
C23	0.0461 (8)	0.0636 (10)	0.0573 (9)	−0.0150 (7)	−0.0014 (7)	−0.0222 (7)
C24	0.0425 (7)	0.0656 (10)	0.0590 (9)	−0.0173 (7)	0.0061 (6)	−0.0295 (8)
C25	0.0480 (9)	0.0800 (13)	0.0818 (12)	−0.0176 (9)	0.0163 (8)	−0.0357 (10)
C26	0.0579 (11)	0.0999 (16)	0.0936 (15)	−0.0319 (11)	0.0328 (10)	−0.0480 (13)
C27	0.0767 (12)	0.0946 (15)	0.0687 (12)	−0.0479 (12)	0.0312 (10)	−0.0330 (11)
C28	0.0625 (10)	0.0700 (11)	0.0579 (10)	−0.0283 (9)	0.0129 (8)	−0.0246 (8)
C29	0.0456 (7)	0.0637 (9)	0.0492 (8)	−0.0224 (7)	0.0088 (6)	−0.0271 (7)

Geometric parameters (Å, º)

O1—C2	1.376 (2)	C13—C14	1.374 (3)
O1—C3	1.440 (2)	C13—H13	0.94 (2)
O2—C3	1.427 (2)	C14—C15	1.386 (2)
O2—C16	1.453 (2)	C14—H14	1.02 (2)
O3—C17	1.210 (2)	C15—H15	0.99 (2)
N1—C2	1.273 (2)	C16—C29	1.506 (2)
N1—C1	1.449 (2)	C16—C17	1.519 (2)
C1—C3	1.543 (2)	C17—C18	1.475 (2)
C1—C16	1.586 (2)	C18—C19	1.397 (2)
C1—H1	0.98 (1)	C18—C23	1.401 (2)
C2—C10	1.472 (2)	C19—C20	1.370 (3)
C3—C4	1.498 (2)	C19—H19	0.95 (2)
C4—C9	1.384 (2)	C20—C21	1.373 (3)
C4—C5	1.386 (2)	C20—H20	0.97 (3)
C5—C6	1.381 (2)	C21—C22	1.379 (3)
C5—H5	0.95 (2)	C21—H21	0.99 (3)
C6—C7	1.380 (3)	C22—C23	1.399 (3)
C6—H6	0.98 (2)	C22—H22	0.97 (2)
C7—C8	1.371 (3)	C23—C24	1.484 (2)
C7—H7	0.92 (2)	C24—C25	1.397 (2)
C8—C9	1.385 (2)	C24—C29	1.401 (2)
C8—H8	0.98 (2)	C25—C26	1.373 (3)
C9—H9	0.98 (2)	C25—H25	1.00 (2)
C10—C15	1.388 (2)	C26—C27	1.373 (3)
C10—C11	1.390 (2)	C26—H26	0.95 (2)
C11—C12	1.379 (2)	C27—C28	1.395 (3)
C11—H11	0.97 (2)	C27—H27	0.96 (2)
C12—C13	1.377 (3)	C28—C29	1.387 (2)
C12—H12	0.93 (2)	C28—H28	0.94 (2)
C2—O1—C3	106.21 (10)	C15—C14—H14	119.5 (12)
C3—O2—C16	93.61 (10)	C14—C15—C10	119.59 (16)
C2—N1—C1	106.09 (11)	C14—C15—H15	121.4 (11)
N1—C1—C3	106.41 (11)	C10—C15—H15	119.0 (11)
N1—C1—C16	115.48 (11)	O2—C16—C29	113.76 (12)
C3—C1—C16	84.30 (10)	O2—C16—C17	111.97 (12)
N1—C1—H1	113.5 (8)	C29—C16—C17	112.09 (12)
C3—C1—H1	119.1 (8)	O2—C16—C1	89.65 (10)
C16—C1—H1	114.9 (8)	C29—C16—C1	117.80 (11)
N1—C2—O1	118.30 (12)	C17—C16—C1	109.71 (12)
N1—C2—C10	126.70 (12)	O3—C17—C18	123.45 (15)
O1—C2—C10	114.99 (11)	O3—C17—C16	121.60 (15)
O2—C3—O1	110.99 (10)	C18—C17—C16	114.79 (13)
O2—C3—C4	114.51 (11)	C19—C18—C23	120.70 (17)
O1—C3—C4	109.77 (11)	C19—C18—C17	119.86 (16)
O2—C3—C1	92.36 (10)	C23—C18—C17	119.44 (14)
O1—C3—C1	102.96 (10)	C20—C19—C18	120.5 (2)
C4—C3—C1	124.72 (11)	C20—C19—H19	123.4 (12)
C9—C4—C5	119.37 (14)	C18—C19—H19	116.1 (12)
C9—C4—C3	120.52 (13)	C19—C20—C21	119.4 (2)
C5—C4—C3	120.05 (13)	C19—C20—H20	119.6 (15)
C6—C5—C4	120.31 (17)	C21—C20—H20	121.0 (15)
C6—C5—H5	119.7 (12)	C20—C21—C22	121.1 (2)
C4—C5—H5	120.0 (12)	C20—C21—H21	118.0 (15)
C7—C6—C5	120.05 (19)	C22—C21—H21	120.8 (15)
C7—C6—H6	121.1 (13)	C21—C22—C23	120.9 (2)
C5—C6—H6	118.8 (13)	C21—C22—H22	119.8 (13)
C8—C7—C6	119.83 (17)	C23—C22—H22	119.3 (13)
C8—C7—H7	120.4 (13)	C22—C23—C18	117.40 (17)
C6—C7—H7	119.8 (13)	C22—C23—C24	123.02 (16)
C7—C8—C9	120.58 (17)	C18—C23—C24	119.50 (15)
C7—C8—H8	119.8 (12)	C25—C24—C29	118.46 (16)
C9—C8—H8	119.6 (12)	C25—C24—C23	121.60 (16)
C4—C9—C8	119.82 (16)	C29—C24—C23	119.92 (13)
C4—C9—H9	119.2 (11)	C26—C25—C24	120.96 (19)
C8—C9—H9	120.9 (11)	C26—C25—H25	119.7 (13)
C15—C10—C11	120.01 (14)	C24—C25—H25	119.3 (13)
C15—C10—C2	120.19 (13)	C27—C26—C25	120.36 (18)
C11—C10—C2	119.80 (13)	C27—C26—H26	118.7 (13)
C12—C11—C10	119.41 (16)	C25—C26—H26	120.9 (13)
C12—C11—H11	122.5 (11)	C26—C27—C28	120.21 (19)
C10—C11—H11	118.1 (11)	C26—C27—H27	122.2 (13)
C13—C12—C11	120.70 (17)	C28—C27—H27	117.6 (13)
C13—C12—H12	119.5 (12)	C29—C28—C27	119.61 (19)
C11—C12—H12	119.7 (12)	C29—C28—H28	116.8 (11)
C14—C13—C12	119.92 (16)	C27—C28—H28	123.6 (11)
C14—C13—H13	120.4 (12)	C28—C29—C24	120.39 (15)
C12—C13—H13	119.6 (12)	C28—C29—C16	120.79 (15)
C13—C14—C15	120.35 (17)	C24—C29—C16	118.80 (13)
C13—C14—H14	120.1 (12)
C2—N1—C1—C3	−1.50 (14)	C3—C1—C16—O2	1.97 (9)
C2—N1—C1—C16	89.97 (14)	N1—C1—C16—C29	13.38 (18)
C1—N1—C2—O1	1.84 (16)	C3—C1—C16—C29	118.86 (13)
C1—N1—C2—C10	−179.09 (12)	N1—C1—C16—C17	143.21 (12)
C3—O1—C2—N1	−1.36 (16)	C3—C1—C16—C17	−111.31 (12)
C3—O1—C2—C10	179.47 (11)	O2—C16—C17—O3	−10.6 (2)
C16—O2—C3—O1	107.03 (11)	C29—C16—C17—O3	−139.84 (18)
C16—O2—C3—C4	−128.00 (12)	C1—C16—C17—O3	87.3 (2)
C16—O2—C3—C1	2.19 (10)	O2—C16—C17—C18	173.94 (12)
C2—O1—C3—O2	−97.46 (12)	C29—C16—C17—C18	44.69 (18)
C2—O1—C3—C4	134.95 (11)	C1—C16—C17—C18	−88.16 (15)
C2—O1—C3—C1	0.22 (13)	O3—C17—C18—C19	−22.2 (3)
N1—C1—C3—O2	112.91 (11)	C16—C17—C18—C19	153.13 (15)
C16—C1—C3—O2	−2.0 (1)	O3—C17—C18—C23	157.90 (18)
N1—C1—C3—O1	0.8 (1)	C16—C17—C18—C23	−26.7 (2)
C16—C1—C3—O1	−114.18 (11)	C23—C18—C19—C20	1.4 (3)
N1—C1—C3—C4	−124.83 (13)	C17—C18—C19—C20	−178.45 (17)
C16—C1—C3—C4	120.25 (14)	C18—C19—C20—C21	−0.3 (3)
O2—C3—C4—C9	16.42 (19)	C19—C20—C21—C22	−0.8 (4)
O1—C3—C4—C9	142.02 (13)	C20—C21—C22—C23	0.7 (4)
C1—C3—C4—C9	−95.36 (17)	C21—C22—C23—C18	0.4 (3)
O2—C3—C4—C5	−166.27 (14)	C21—C22—C23—C24	−176.27 (18)
O1—C3—C4—C5	−40.67 (18)	C19—C18—C23—C22	−1.5 (2)
C1—C3—C4—C5	81.95 (18)	C17—C18—C23—C22	178.39 (15)
C9—C4—C5—C6	−1.0 (3)	C19—C18—C23—C24	175.37 (15)
C3—C4—C5—C6	−178.33 (17)	C17—C18—C23—C24	−4.8 (2)
C4—C5—C6—C7	−1.1 (3)	C22—C23—C24—C25	16.2 (2)
C5—C6—C7—C8	2.2 (3)	C18—C23—C24—C25	−160.47 (15)
C6—C7—C8—C9	−1.1 (3)	C22—C23—C24—C29	−165.68 (15)
C5—C4—C9—C8	2.1 (2)	C18—C23—C24—C29	17.7 (2)
C3—C4—C9—C8	179.40 (14)	C29—C24—C25—C26	0.8 (3)
C7—C8—C9—C4	−1.0 (3)	C23—C24—C25—C26	178.93 (17)
N1—C2—C10—C15	158.65 (15)	C24—C25—C26—C27	−0.5 (3)
O1—C2—C10—C15	−22.26 (19)	C25—C26—C27—C28	−0.1 (3)
N1—C2—C10—C11	−21.5 (2)	C26—C27—C28—C29	0.4 (3)
O1—C2—C10—C11	157.56 (13)	C27—C28—C29—C24	−0.1 (2)
C15—C10—C11—C12	0.0 (2)	C27—C28—C29—C16	178.35 (15)
C2—C10—C11—C12	−179.80 (14)	C25—C24—C29—C28	−0.4 (2)
C10—C11—C12—C13	−1.4 (3)	C23—C24—C29—C28	−178.63 (14)
C11—C12—C13—C14	1.4 (3)	C25—C24—C29—C16	−178.96 (14)
C12—C13—C14—C15	−0.1 (3)	C23—C24—C29—C16	2.8 (2)
C13—C14—C15—C10	−1.2 (3)	O2—C16—C29—C28	20.00 (19)
C11—C10—C15—C14	1.3 (2)	C17—C16—C29—C28	148.30 (15)
C2—C10—C15—C14	−178.93 (15)	C1—C16—C29—C28	−82.98 (18)
C3—O2—C16—C29	−122.58 (12)	O2—C16—C29—C24	−161.49 (12)
C3—O2—C16—C17	109.05 (12)	C17—C16—C29—C24	−33.18 (19)
C3—O2—C16—C1	−2.13 (10)	C1—C16—C29—C24	95.53 (16)
N1—C1—C16—O2	−103.51 (12)