(1S,1'S,2'R,4a'S,9a'S,9b'R)-1'-Acet-yloxy-2,4'-dioxo-2',4',4a',7',8',9',9a',9b'-octa-hydro-1'H,2H-spiro-[ace-naphthyl-ene-1,5'-pyrano[4,3-a]pyrrolizin]-2'-ylmethyl acetate.

In the title compound C26H25NO7, the mean plane through the lactone-substituted ring of the pyrrolizidine moiety forms dihedral angles of 78.46 (6) and 58.28 (8)° with the ace-naphthyl-ene moiety and the sugar based-lactone ring, respectively. The sum of the angles at the the N atom of the pyrrolizidine ring (335.0°) is in accordance with sp (3) hybridization. Some atoms of the acetate group are disordered and were refined using a split model [occupancy ratio 0.673 (10):0.327 (10)].

Related literature

For the importance of pyrrolidine and pyrrolizidine compounds and background to this work, see: Boido et al. (1994 ▶); Cravotto et al. (2001 ▶); Gershbein (1975 ▶); Govind et al. (2003 ▶); Jellimann et al. (2000 ▶); Nishimura et al. (1985 ▶); Selvanayagam et al. (2004 ▶); Usha et al. (2005 ▶).

Experimental

Crystal data

C26H25NO7

M = 463.47

Tetragonal,

a = 13.6792 (3) Å

c = 24.9625 (13) Å

V = 4671.0 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 295 K

0.30 × 0.30 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.902, T max = 0.976

21173 measured reflections

4010 independent reflections

2923 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.104

S = 1.06

4010 reflections

367 parameters

138 restraints

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.12 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813026111/nc2316sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813026111/nc2316Isup2.hkl

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

C26H25NO7	Dx = 1.318 Mg m−3
Mr = 463.47	Melting point: 481.15 K
Tetragonal, P43212	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P4nw2abw	Cell parameters from 5405 reflections
a = 13.6792 (3) Å	θ = 2.2–22.2°
c = 24.9625 (13) Å	µ = 0.10 mm−1
V = 4671.0 (3) Å3	T = 295 K
Z = 8	Block, yellow
F(000) = 1952	0.30 × 0.30 × 0.25 mm

Bruker Kappa APEXII CCD diffractometer	4010 independent reflections
Radiation source: fine-focus sealed tube	2923 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
ω and φ scan	θmax = 25.1°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −16→16
Tmin = 0.902, Tmax = 0.976	k = −11→16
21173 measured reflections	l = −27→28

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042	H-atom parameters constrained
wR(F2) = 0.104	w = 1/[σ2(Fo2) + (0.0494P)2 + 0.438P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
4010 reflections	Δρmax = 0.24 e Å−3
367 parameters	Δρmin = −0.12 e Å−3
138 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0038 (5)

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	Occ. (<1)
C1	0.49450 (18)	0.37963 (17)	0.34572 (10)	0.0529 (6)
C2	0.52973 (19)	0.38194 (18)	0.40078 (10)	0.0567 (7)
C3	0.5995 (2)	0.4377 (2)	0.42606 (12)	0.0727 (8)
H3	0.6377	0.4823	0.4073	0.087*
C4	0.6103 (2)	0.4243 (3)	0.48143 (14)	0.0894 (10)
H4	0.6574	0.4609	0.4994	0.107*
C5	0.5552 (3)	0.3604 (3)	0.51006 (13)	0.0843 (9)
H5	0.5649	0.3551	0.5468	0.101*
C6	0.4840 (2)	0.3023 (2)	0.48530 (10)	0.0650 (7)
C7	0.4197 (2)	0.2338 (2)	0.50876 (12)	0.0785 (9)
H7	0.4215	0.2233	0.5456	0.094*
C8	0.3560 (2)	0.1837 (2)	0.47842 (11)	0.0763 (8)
H8	0.3157	0.1380	0.4949	0.092*
C9	0.3474 (2)	0.19735 (19)	0.42248 (11)	0.0660 (7)
H9	0.3017	0.1621	0.4028	0.079*
C10	0.40725 (18)	0.26315 (17)	0.39801 (9)	0.0522 (6)
C11	0.47403 (18)	0.31481 (17)	0.42968 (9)	0.0538 (6)
C12	0.41909 (17)	0.29582 (17)	0.34043 (9)	0.0508 (6)
C13	0.4556 (3)	0.1226 (2)	0.31434 (13)	0.0898 (10)
H13A	0.3875	0.1058	0.3201	0.108*
H13B	0.4939	0.1007	0.3448	0.108*
C14	0.4941 (3)	0.0793 (2)	0.26195 (13)	0.0945 (11)
H14A	0.5650	0.0791	0.2612	0.113*
H14B	0.4704	0.0131	0.2567	0.113*
C15	0.4528 (3)	0.1477 (2)	0.22047 (12)	0.0893 (10)
H15A	0.3920	0.1224	0.2061	0.107*
H15B	0.4987	0.1568	0.1913	0.107*
C16	0.4355 (2)	0.24436 (19)	0.25035 (10)	0.0639 (7)
H16	0.4763	0.2958	0.2346	0.077*
C17	0.33003 (19)	0.28012 (19)	0.25462 (9)	0.0587 (7)
H17	0.2867	0.2230	0.2540	0.070*
C18	0.32353 (17)	0.32766 (17)	0.31052 (9)	0.0505 (6)
H18	0.2686	0.2968	0.3292	0.061*
C19	0.30811 (17)	0.43601 (18)	0.31357 (10)	0.0532 (6)
C20	0.34631 (19)	0.44821 (18)	0.21942 (9)	0.0567 (6)
H20	0.4167	0.4371	0.2235	0.068*
C21	0.2963 (2)	0.3508 (2)	0.21183 (9)	0.0607 (7)
H21	0.2252	0.3589	0.2135	0.073*
C22	0.33054 (19)	0.5216 (2)	0.17621 (10)	0.0660 (7)
H22A	0.3560	0.5847	0.1873	0.079*
H22B	0.3646	0.5016	0.1439	0.079*
N1	0.46742 (16)	0.22513 (15)	0.30539 (8)	0.0636 (6)
O1	0.51791 (14)	0.43233 (14)	0.30886 (7)	0.0734 (6)
O2	0.30863 (12)	0.49008 (12)	0.26880 (6)	0.0599 (4)
O3	0.29131 (15)	0.47673 (14)	0.35530 (7)	0.0734 (5)
O5	0.22688 (12)	0.52899 (14)	0.16582 (7)	0.0674 (5)
O4	0.32451 (17)	0.31189 (15)	0.16054 (7)	0.0873 (7)
O6	0.2533 (3)	0.5940 (6)	0.08779 (18)	0.108 (2)	0.673 (10)
C23	0.1979 (6)	0.5579 (7)	0.1189 (2)	0.066 (2)	0.673 (10)
C24	0.0924 (7)	0.5520 (13)	0.1066 (6)	0.082 (3)	0.673 (10)
H24A	0.0823	0.5635	0.0691	0.123*	0.673 (10)
H24B	0.0579	0.6005	0.1270	0.123*	0.673 (10)
H24C	0.0685	0.4882	0.1158	0.123*	0.673 (10)
O6'	0.2525 (6)	0.5122 (12)	0.0794 (3)	0.101 (4)	0.327 (10)
C23'	0.1997 (12)	0.5354 (18)	0.1156 (4)	0.073 (4)	0.327 (10)
C24'	0.0906 (13)	0.540 (3)	0.1196 (11)	0.072 (5)	0.327 (10)
H24D	0.0625	0.4829	0.1039	0.109*	0.327 (10)
H24E	0.0674	0.5973	0.1009	0.109*	0.327 (10)
H24F	0.0718	0.5444	0.1566	0.109*	0.327 (10)
O7	0.1627 (7)	0.3021 (9)	0.1393 (4)	0.114 (3)	0.673 (10)
C25	0.2479 (7)	0.2915 (16)	0.1279 (5)	0.105 (3)	0.673 (10)
C26	0.2787 (9)	0.2525 (11)	0.0740 (5)	0.143 (4)	0.673 (10)
H26A	0.3158	0.1936	0.0787	0.215*	0.673 (10)
H26B	0.3182	0.3003	0.0560	0.215*	0.673 (10)
H26C	0.2217	0.2388	0.0528	0.215*	0.673 (10)
O7'	0.1851 (18)	0.3144 (19)	0.1230 (9)	0.122 (5)	0.327 (10)
C25'	0.2665 (17)	0.282 (3)	0.1209 (12)	0.112 (4)	0.327 (10)
C26'	0.3264 (19)	0.2324 (18)	0.0783 (9)	0.119 (6)	0.327 (10)
H26D	0.2952	0.1724	0.0680	0.178*	0.327 (10)
H26E	0.3905	0.2186	0.0921	0.178*	0.327 (10)
H26F	0.3318	0.2745	0.0477	0.178*	0.327 (10)

	U11	U22	U33	U12	U13	U23
C1	0.0599 (16)	0.0540 (15)	0.0449 (16)	0.0000 (11)	0.0005 (12)	0.0049 (12)
C2	0.0620 (16)	0.0603 (16)	0.0476 (16)	0.0012 (12)	−0.0052 (13)	−0.0022 (12)
C3	0.0722 (19)	0.081 (2)	0.065 (2)	−0.0042 (15)	−0.0190 (15)	−0.0035 (15)
C4	0.093 (2)	0.097 (3)	0.078 (3)	−0.0003 (19)	−0.0338 (19)	−0.0095 (19)
C5	0.104 (3)	0.095 (2)	0.0541 (19)	0.026 (2)	−0.0200 (18)	−0.0050 (17)
C6	0.083 (2)	0.0668 (17)	0.0449 (17)	0.0219 (14)	−0.0037 (15)	0.0061 (14)
C7	0.105 (2)	0.084 (2)	0.0463 (18)	0.0269 (18)	0.0066 (18)	0.0209 (16)
C8	0.100 (2)	0.0702 (19)	0.059 (2)	0.0063 (16)	0.0176 (17)	0.0228 (16)
C9	0.0806 (19)	0.0600 (17)	0.0573 (18)	−0.0029 (13)	0.0101 (14)	0.0101 (13)
C10	0.0684 (16)	0.0467 (14)	0.0416 (15)	0.0005 (11)	0.0042 (12)	0.0068 (11)
C11	0.0700 (16)	0.0531 (14)	0.0382 (15)	0.0124 (12)	0.0000 (12)	0.0057 (11)
C12	0.0618 (15)	0.0496 (14)	0.0410 (15)	−0.0057 (11)	0.0025 (11)	0.0001 (11)
C13	0.120 (3)	0.066 (2)	0.084 (2)	0.0018 (17)	0.0054 (19)	−0.0087 (17)
C14	0.128 (3)	0.0651 (19)	0.091 (2)	0.0087 (19)	0.010 (2)	−0.0184 (18)
C15	0.113 (3)	0.082 (2)	0.072 (2)	0.0072 (19)	0.0118 (18)	−0.0235 (17)
C16	0.083 (2)	0.0637 (17)	0.0446 (17)	−0.0005 (13)	0.0097 (13)	−0.0034 (12)
C17	0.0706 (17)	0.0619 (16)	0.0438 (16)	−0.0159 (12)	0.0010 (12)	−0.0035 (12)
C18	0.0568 (15)	0.0555 (15)	0.0392 (15)	−0.0135 (10)	0.0036 (11)	0.0000 (11)
C19	0.0559 (15)	0.0629 (17)	0.0409 (16)	−0.0026 (11)	−0.0021 (12)	0.0011 (13)
C20	0.0592 (15)	0.0716 (17)	0.0392 (15)	−0.0074 (12)	0.0031 (11)	0.0029 (12)
C21	0.0710 (17)	0.0756 (18)	0.0357 (15)	−0.0145 (14)	−0.0006 (12)	−0.0027 (13)
C22	0.0589 (17)	0.0831 (19)	0.0559 (17)	−0.0138 (13)	−0.0011 (13)	0.0119 (14)
N1	0.0864 (16)	0.0562 (14)	0.0481 (14)	0.0016 (11)	0.0048 (11)	−0.0009 (10)
O1	0.0849 (13)	0.0802 (13)	0.0552 (12)	−0.0292 (10)	−0.0069 (10)	0.0176 (10)
O2	0.0759 (12)	0.0608 (11)	0.0430 (10)	−0.0020 (8)	−0.0031 (8)	0.0035 (8)
O3	0.1011 (14)	0.0731 (12)	0.0459 (11)	0.0151 (10)	0.0021 (9)	−0.0077 (10)
O5	0.0635 (12)	0.0933 (13)	0.0453 (11)	−0.0059 (9)	−0.0001 (9)	0.0081 (9)
O4	0.1211 (18)	0.1029 (16)	0.0377 (12)	−0.0152 (13)	−0.0072 (11)	−0.0139 (11)
O6	0.092 (3)	0.157 (5)	0.075 (3)	0.024 (3)	0.018 (2)	0.060 (3)
C23	0.075 (3)	0.080 (5)	0.042 (3)	0.012 (3)	0.002 (3)	0.001 (2)
C24	0.082 (4)	0.087 (5)	0.076 (7)	0.001 (3)	−0.015 (4)	0.002 (6)
O6'	0.096 (5)	0.158 (9)	0.050 (4)	0.004 (5)	0.015 (4)	0.012 (5)
C23'	0.069 (6)	0.101 (8)	0.049 (6)	−0.010 (5)	0.000 (5)	0.001 (5)
C24'	0.083 (7)	0.089 (10)	0.046 (8)	0.010 (7)	−0.036 (6)	−0.015 (8)
O7	0.144 (5)	0.126 (4)	0.072 (5)	−0.050 (3)	−0.041 (4)	0.001 (4)
C25	0.165 (7)	0.095 (6)	0.054 (5)	−0.022 (6)	−0.024 (6)	−0.010 (4)
C26	0.214 (10)	0.159 (8)	0.056 (5)	0.001 (8)	−0.032 (6)	−0.027 (5)
O7'	0.186 (12)	0.110 (8)	0.071 (10)	−0.011 (9)	−0.041 (8)	−0.007 (7)
C25'	0.179 (8)	0.098 (7)	0.058 (7)	−0.028 (7)	−0.022 (7)	0.003 (6)
C26'	0.210 (16)	0.106 (9)	0.040 (7)	0.004 (11)	−0.027 (10)	−0.021 (6)

C1—O1	1.212 (3)	C17—H17	0.9800
C1—C2	1.457 (3)	C18—C19	1.499 (3)
C1—C12	1.548 (3)	C18—H18	0.9800
C2—C3	1.375 (4)	C19—O3	1.203 (3)
C2—C11	1.394 (3)	C19—O2	1.340 (3)
C3—C4	1.402 (4)	C20—O2	1.454 (3)
C3—H3	0.9300	C20—C22	1.490 (3)
C4—C5	1.357 (5)	C20—C21	1.509 (4)
C4—H4	0.9300	C20—H20	0.9800
C5—C6	1.401 (4)	C21—O4	1.439 (3)
C5—H5	0.9300	C21—H21	0.9800
C6—C11	1.405 (3)	C22—O5	1.445 (3)
C6—C7	1.412 (4)	C22—H22A	0.9700
C7—C8	1.343 (4)	C22—H22B	0.9700
C7—H7	0.9300	O5—C23	1.299 (6)
C8—C9	1.414 (4)	O5—C23'	1.310 (9)
C8—H8	0.9300	O4—C25'	1.333 (10)
C9—C10	1.362 (3)	O4—C25	1.356 (7)
C9—H9	0.9300	O6—C23	1.192 (7)
C10—C11	1.400 (3)	C23—C24	1.477 (7)
C10—C12	1.514 (3)	C24—H24A	0.9600
C12—N1	1.462 (3)	C24—H24B	0.9600
C12—C18	1.567 (3)	C24—H24C	0.9600
C13—N1	1.429 (4)	O6'—C23'	1.199 (9)
C13—C14	1.529 (4)	C23'—C24'	1.498 (10)
C13—H13A	0.9700	C24'—H24D	0.9600
C13—H13B	0.9700	C24'—H24E	0.9600
C14—C15	1.505 (4)	C24'—H24F	0.9600
C14—H14A	0.9700	O7—C25	1.210 (8)
C14—H14B	0.9700	C25—C26	1.508 (8)
C15—C16	1.537 (4)	C26—H26A	0.9600
C15—H15A	0.9700	C26—H26B	0.9600
C15—H15B	0.9700	C26—H26C	0.9600
C16—N1	1.465 (3)	O7'—C25'	1.199 (10)
C16—C17	1.527 (4)	C25'—C26'	1.504 (10)
C16—H16	0.9800	C26'—H26D	0.9600
C17—C21	1.513 (3)	C26'—H26E	0.9600
C17—C18	1.542 (3)	C26'—H26F	0.9600
O1—C1—C2	128.0 (2)	C16—C17—C18	104.6 (2)
O1—C1—C12	123.5 (2)	C21—C17—H17	108.3
C2—C1—C12	108.5 (2)	C16—C17—H17	108.3
C3—C2—C11	120.5 (2)	C18—C17—H17	108.3
C3—C2—C1	132.4 (3)	C19—C18—C17	118.1 (2)
C11—C2—C1	107.0 (2)	C19—C18—C12	111.59 (18)
C2—C3—C4	116.9 (3)	C17—C18—C12	105.41 (19)
C2—C3—H3	121.5	C19—C18—H18	107.1
C4—C3—H3	121.5	C17—C18—H18	107.1
C5—C4—C3	123.0 (3)	C12—C18—H18	107.1
C5—C4—H4	118.5	O3—C19—O2	117.9 (2)
C3—C4—H4	118.5	O3—C19—C18	121.9 (2)
C4—C5—C6	121.3 (3)	O2—C19—C18	120.2 (2)
C4—C5—H5	119.4	O2—C20—C22	107.3 (2)
C6—C5—H5	119.4	O2—C20—C21	107.08 (18)
C5—C6—C11	115.7 (3)	C22—C20—C21	116.0 (2)
C5—C6—C7	128.8 (3)	O2—C20—H20	108.8
C11—C6—C7	115.5 (3)	C22—C20—H20	108.8
C8—C7—C6	120.6 (3)	C21—C20—H20	108.8
C8—C7—H7	119.7	O4—C21—C20	108.5 (2)
C6—C7—H7	119.7	O4—C21—C17	108.0 (2)
C7—C8—C9	122.9 (3)	C20—C21—C17	109.7 (2)
C7—C8—H8	118.5	O4—C21—H21	110.2
C9—C8—H8	118.5	C20—C21—H21	110.2
C10—C9—C8	118.7 (3)	C17—C21—H21	110.2
C10—C9—H9	120.6	O5—C22—C20	108.6 (2)
C8—C9—H9	120.6	O5—C22—H22A	110.0
C9—C10—C11	118.2 (2)	C20—C22—H22A	110.0
C9—C10—C12	133.3 (2)	O5—C22—H22B	110.0
C11—C10—C12	108.51 (19)	C20—C22—H22B	110.0
C2—C11—C10	113.4 (2)	H22A—C22—H22B	108.3
C2—C11—C6	122.6 (2)	C13—N1—C12	120.3 (2)
C10—C11—C6	124.0 (2)	C13—N1—C16	106.8 (2)
N1—C12—C10	114.91 (19)	C12—N1—C16	107.92 (19)
N1—C12—C1	103.87 (19)	C19—O2—C20	119.44 (19)
C10—C12—C1	102.06 (19)	C23—O5—C23'	14.1 (14)
N1—C12—C18	106.01 (17)	C23—O5—C22	118.9 (4)
C10—C12—C18	116.43 (19)	C23'—O5—C22	117.1 (7)
C1—C12—C18	113.00 (19)	C25'—O4—C25	14.2 (14)
N1—C13—C14	102.0 (2)	C25'—O4—C21	127.9 (12)
N1—C13—H13A	111.4	C25—O4—C21	113.8 (5)
C14—C13—H13A	111.4	O6—C23—O5	121.3 (7)
N1—C13—H13B	111.4	O6—C23—C24	120.6 (7)
C14—C13—H13B	111.4	O5—C23—C24	117.9 (7)
H13A—C13—H13B	109.2	O6'—C23'—O5	122.1 (12)
C15—C14—C13	102.6 (3)	O6'—C23'—C24'	131.5 (16)
C15—C14—H14A	111.2	O5—C23'—C24'	102.8 (13)
C13—C14—H14A	111.2	C23'—C24'—H24D	109.5
C15—C14—H14B	111.2	C23'—C24'—H24E	109.5
C13—C14—H14B	111.2	H24D—C24'—H24E	109.5
H14A—C14—H14B	109.2	C23'—C24'—H24F	109.5
C14—C15—C16	105.0 (2)	H24D—C24'—H24F	109.5
C14—C15—H15A	110.7	H24E—C24'—H24F	109.5
C16—C15—H15A	110.7	O7—C25—O4	125.4 (8)
C14—C15—H15B	110.7	O7—C25—C26	121.5 (8)
C16—C15—H15B	110.7	O4—C25—C26	113.2 (8)
H15A—C15—H15B	108.8	O7'—C25'—O4	114 (2)
N1—C16—C17	105.9 (2)	O7'—C25'—C26'	134.7 (18)
N1—C16—C15	104.8 (2)	O4—C25'—C26'	109.8 (16)
C17—C16—C15	117.1 (2)	C25'—C26'—H26D	109.5
N1—C16—H16	109.6	C25'—C26'—H26E	109.5
C17—C16—H16	109.6	H26D—C26'—H26E	109.5
C15—C16—H16	109.6	C25'—C26'—H26F	109.5
C21—C17—C16	116.3 (2)	H26D—C26'—H26F	109.5
C21—C17—C18	110.6 (2)	H26E—C26'—H26F	109.5
O1—C1—C2—C3	−3.5 (5)	N1—C12—C18—C17	−6.9 (2)
C12—C1—C2—C3	176.4 (3)	C10—C12—C18—C17	−136.1 (2)
O1—C1—C2—C11	173.5 (3)	C1—C12—C18—C17	106.2 (2)
C12—C1—C2—C11	−6.6 (3)	C17—C18—C19—O3	171.5 (2)
C11—C2—C3—C4	−0.7 (4)	C12—C18—C19—O3	−66.2 (3)
C1—C2—C3—C4	176.0 (3)	C17—C18—C19—O2	−5.7 (3)
C2—C3—C4—C5	−0.5 (5)	C12—C18—C19—O2	116.7 (2)
C3—C4—C5—C6	0.8 (5)	O2—C20—C21—O4	174.2 (2)
C4—C5—C6—C11	0.1 (4)	C22—C20—C21—O4	54.5 (3)
C4—C5—C6—C7	−179.0 (3)	O2—C20—C21—C17	−67.9 (3)
C5—C6—C7—C8	−179.5 (3)	C22—C20—C21—C17	172.3 (2)
C11—C6—C7—C8	1.5 (4)	C16—C17—C21—O4	48.0 (3)
C6—C7—C8—C9	−1.5 (5)	C18—C17—C21—O4	167.1 (2)
C7—C8—C9—C10	1.0 (4)	C16—C17—C21—C20	−70.2 (3)
C8—C9—C10—C11	−0.5 (4)	C18—C17—C21—C20	49.0 (3)
C8—C9—C10—C12	179.6 (3)	O2—C20—C22—O5	−69.4 (3)
C3—C2—C11—C10	−179.3 (2)	C21—C20—C22—O5	50.2 (3)
C1—C2—C11—C10	3.3 (3)	C14—C13—N1—C12	165.8 (2)
C3—C2—C11—C6	1.6 (4)	C14—C13—N1—C16	42.5 (3)
C1—C2—C11—C6	−175.8 (2)	C10—C12—N1—C13	32.2 (3)
C9—C10—C11—C2	−178.4 (2)	C1—C12—N1—C13	142.8 (3)
C12—C10—C11—C2	1.5 (3)	C18—C12—N1—C13	−97.9 (3)
C9—C10—C11—C6	0.7 (4)	C10—C12—N1—C16	154.9 (2)
C12—C10—C11—C6	−179.4 (2)	C1—C12—N1—C16	−94.5 (2)
C5—C6—C11—C2	−1.3 (4)	C18—C12—N1—C16	24.9 (2)
C7—C6—C11—C2	177.9 (2)	C17—C16—N1—C13	97.3 (2)
C5—C6—C11—C10	179.7 (3)	C15—C16—N1—C13	−27.0 (3)
C7—C6—C11—C10	−1.1 (4)	C17—C16—N1—C12	−33.3 (2)
C9—C10—C12—N1	−73.7 (4)	C15—C16—N1—C12	−157.7 (2)
C11—C10—C12—N1	106.4 (2)	O3—C19—O2—C20	168.5 (2)
C9—C10—C12—C1	174.6 (3)	C18—C19—O2—C20	−14.3 (3)
C11—C10—C12—C1	−5.3 (3)	C22—C20—O2—C19	175.71 (19)
C9—C10—C12—C18	51.1 (4)	C21—C20—O2—C19	50.5 (3)
C11—C10—C12—C18	−128.8 (2)	C20—C22—O5—C23	−154.5 (5)
O1—C1—C12—N1	67.3 (3)	C20—C22—O5—C23'	−138.6 (12)
C2—C1—C12—N1	−112.6 (2)	C20—C21—O4—C25'	−126 (3)
O1—C1—C12—C10	−173.0 (2)	C17—C21—O4—C25'	115 (3)
C2—C1—C12—C10	7.2 (3)	C20—C21—O4—C25	−123.5 (11)
O1—C1—C12—C18	−47.1 (3)	C17—C21—O4—C25	117.6 (11)
C2—C1—C12—C18	133.0 (2)	C23'—O5—C23—O6	−99 (4)
N1—C13—C14—C15	−41.0 (3)	C22—O5—C23—O6	−13.0 (10)
C13—C14—C15—C16	24.4 (3)	C23'—O5—C23—C24	85 (5)
C14—C15—C16—N1	0.1 (3)	C22—O5—C23—C24	171.8 (9)
C14—C15—C16—C17	−116.8 (3)	C23—O5—C23'—O6'	119 (6)
N1—C16—C17—C21	149.9 (2)	C22—O5—C23'—O6'	18 (3)
C15—C16—C17—C21	−93.8 (3)	C23—O5—C23'—C24'	−80 (4)
N1—C16—C17—C18	27.6 (2)	C22—O5—C23'—C24'	179.3 (14)
C15—C16—C17—C18	143.9 (2)	C25'—O4—C25—O7	171 (15)
C21—C17—C18—C19	−12.9 (3)	C21—O4—C25—O7	−1 (3)
C16—C17—C18—C19	113.0 (2)	C25'—O4—C25—C26	−9 (12)
C21—C17—C18—C12	−138.4 (2)	C21—O4—C25—C26	178.9 (10)
C16—C17—C18—C12	−12.4 (2)	C25—O4—C25'—O7'	12 (9)
N1—C12—C18—C19	−136.3 (2)	C21—O4—C25'—O7'	20 (6)
C10—C12—C18—C19	94.5 (2)	C25—O4—C25'—C26'	−180 (16)
C1—C12—C18—C19	−23.2 (3)	C21—O4—C25'—C26'	−171.1 (14)