3β-Acet-oxy-lup-20(29)-en-28-yl 1H-1,2,4-tri-azole-1-carboxyl-ate.

The title triterpene, C(35)H(53)N(3)O(4), is a C-28 carbamate derivative of 3β-acet-oxy-betulin prepared in a one-step reaction from the commercially available 1,1'-carbonyl-di(1,2,4-triazole) (CDT), crystallized from acetone/n-hexane. All rings are trans fused. The carbamate and acetate substituents are in axial and equatorial positions, respectively. A quantum chemical ab initio Roothaan Hartree-Fock calculation of the equilibrium geometry of the isolated mol-ecule gives values for bond lengths and valency angles in close agreement with experimental values. The calculation also reproduces the observed mol-ecular conformation, with puckering parameters that agree well with those determined from the crystallographic study.

Related literature

For the cytotoxic activity of penta­cyclic triterpenoids, see: Petronelli et al. (2009 ▶); Fulda (2009 ▶); Salvador (2010 ▶). For the biological activity of betulin and betulinic acid, see: Dzubak et al. (2006 ▶); Tolstikova et al. (2006 ▶). For the synthesis of carbamate derivatives of betulin and betulinic acid, see: Santos et al. (2009 ▶, 2010b ▶). For related structures, see Santos et al. (2010a ▶). For puckering and asymmetry parameters, see Cremer & Pople (1975 ▶); Duax & Norton (1975 ▶). The quantum chemical calculations were performed with the computer program GAMESS (Schmidt et al., 1993 ▶).

Experimental

Crystal data

C35H53N3O4

M = 579.80

Orthorhombic,

a = 9.2108 (4) Å

b = 15.5383 (6) Å

c = 22.9270 (9) Å

V = 3281.3 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.28 × 0.24 × 0.23 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.880, T max = 1.00

61378 measured reflections

4625 independent reflections

3264 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.137

S = 1.02

4625 reflections

386 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810043515/bt5389sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810043515/bt5389Isup2.hkl

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

C35H53N3O4	Dx = 1.174 Mg m−3
Mr = 579.80	Melting point: 386 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
a = 9.2108 (4) Å	Cell parameters from 5792 reflections
b = 15.5383 (6) Å	θ = 2.6–22.2°
c = 22.9270 (9) Å	µ = 0.08 mm−1
V = 3281.3 (2) Å3	T = 293 K
Z = 4	Triangular prism, colourless
F(000) = 1264	0.28 × 0.24 × 0.23 mm

Bruker APEXII CCD area-detector diffractometer	4625 independent reflections
Radiation source: fine-focus sealed tube	3264 reflections with I > 2σ(I)
graphite	Rint = 0.046
φ and ω scans	θmax = 28.5°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −12→12
Tmin = 0.880, Tmax = 1.00	k = −20→20
61378 measured reflections	l = −30→30

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0682P)2 + 0.4749P] where P = (Fo2 + 2Fc2)/3
4625 reflections	(Δ/σ)max < 0.001
386 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.26 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
C1	0.6151 (3)	−0.06751 (16)	0.10936 (12)	0.0579 (7)
H1A	0.7006	−0.1040	0.1092	0.069*
H1B	0.5885	−0.0574	0.1497	0.069*
C2	0.4912 (4)	−0.11521 (19)	0.07917 (14)	0.0684 (8)
H2A	0.5209	−0.1317	0.0402	0.082*
H2B	0.4683	−0.1672	0.1007	0.082*
C3	0.3584 (3)	−0.05852 (19)	0.07579 (12)	0.0614 (7)
H3	0.3280	−0.0444	0.1156	0.074*
C4	0.3822 (3)	0.02562 (18)	0.04263 (11)	0.0554 (6)
C5	0.5098 (3)	0.07087 (16)	0.07423 (10)	0.0471 (5)
H5	0.4753	0.0779	0.1144	0.057*
C6	0.5400 (3)	0.16314 (17)	0.05369 (12)	0.0563 (7)
H6A	0.5908	0.1617	0.0166	0.068*
H6B	0.4488	0.1932	0.0480	0.068*
C7	0.6316 (3)	0.21111 (16)	0.09849 (12)	0.0556 (6)
H7A	0.5769	0.2156	0.1345	0.067*
H7B	0.6490	0.2691	0.0844	0.067*
C8	0.7783 (3)	0.16820 (14)	0.11152 (10)	0.0446 (5)
C26	0.8744 (3)	0.18187 (17)	0.05709 (10)	0.0548 (6)
H26A	0.8204	0.1671	0.0227	0.082*
H26B	0.9589	0.1459	0.0598	0.082*
H26C	0.9036	0.2411	0.0550	0.082*
C9	0.7526 (3)	0.07045 (14)	0.12451 (9)	0.0433 (5)
H9	0.6988	0.0697	0.1614	0.052*
C10	0.6540 (3)	0.01952 (15)	0.08079 (10)	0.0465 (5)
C25	0.7321 (3)	0.00105 (19)	0.02266 (11)	0.0613 (7)
H25A	0.6960	−0.0517	0.0064	0.092*
H25B	0.8346	−0.0040	0.0295	0.092*
H25C	0.7144	0.0474	−0.0041	0.092*
C11	0.8960 (3)	0.02553 (15)	0.13842 (11)	0.0502 (6)
H11A	0.8764	−0.0338	0.1488	0.060*
H11B	0.9562	0.0253	0.1037	0.060*
C12	0.9794 (3)	0.06810 (16)	0.18781 (11)	0.0531 (6)
H12A	1.0733	0.0405	0.1918	0.064*
H12B	0.9267	0.0600	0.2240	0.064*
C13	1.0015 (3)	0.16425 (15)	0.17724 (10)	0.0466 (5)
H13	1.0561	0.1695	0.1407	0.056*
C14	0.8528 (3)	0.21018 (15)	0.16712 (10)	0.0472 (5)
C27	0.7567 (3)	0.20149 (19)	0.22234 (12)	0.0619 (7)
H27A	0.8041	0.2288	0.2547	0.093*
H27B	0.7419	0.1417	0.2310	0.093*
H27C	0.6646	0.2286	0.2155	0.093*
C15	0.8773 (4)	0.30855 (15)	0.15862 (13)	0.0604 (7)
H15A	0.9208	0.3178	0.1206	0.072*
H15B	0.7835	0.3369	0.1586	0.072*
C16	0.9732 (4)	0.35123 (18)	0.20470 (13)	0.0652 (8)
H16A	0.9896	0.4109	0.1941	0.078*
H16B	0.9238	0.3502	0.2420	0.078*
C17	1.1182 (3)	0.30553 (16)	0.21027 (11)	0.0559 (6)
C18	1.0915 (3)	0.20927 (16)	0.22413 (11)	0.0512 (6)
H18	1.0331	0.2079	0.2598	0.061*
C19	1.2424 (3)	0.17477 (17)	0.24085 (11)	0.0565 (6)
H19	1.2955	0.1624	0.2048	0.068*
C21	1.3161 (4)	0.2544 (2)	0.27089 (16)	0.0756 (9)
H21A	1.3307	0.2435	0.3121	0.091*
H21B	1.4095	0.2663	0.2531	0.091*
C22	1.2130 (4)	0.3306 (2)	0.26217 (14)	0.0734 (9)
H22A	1.1542	0.3398	0.2967	0.088*
H22B	1.2670	0.3828	0.2539	0.088*
O28B	1.4367 (4)	0.38506 (16)	0.09786 (15)	0.1169 (11)
O28A	1.2328 (2)	0.40742 (11)	0.14684 (10)	0.0707 (6)
C28	1.2065 (4)	0.31540 (16)	0.15439 (13)	0.0631 (8)
H28A	1.2978	0.2846	0.1576	0.076*
H28B	1.1531	0.2926	0.1214	0.076*
C28A	1.3511 (3)	0.43009 (17)	0.12090 (12)	0.0579 (7)
C30	1.1593 (5)	0.0930 (3)	0.33192 (15)	0.1015 (13)
H30A	1.0586	0.0914	0.3211	0.152*
H30B	1.1776	0.1434	0.3550	0.152*
H30C	1.1827	0.0426	0.3542	0.152*
C29	1.3388 (5)	0.0314 (2)	0.26551 (18)	0.0934 (12)
H29A	1.3455	−0.0164	0.2897	0.112*
H29B	1.3947	0.0345	0.2318	0.112*
C20	1.2492 (4)	0.0955 (2)	0.27912 (12)	0.0679 (8)
N28A	1.3661 (3)	0.52003 (13)	0.11931 (9)	0.0551 (5)
C28C	1.4730 (4)	0.5648 (2)	0.09318 (16)	0.0800 (10)
H28C	1.5497	0.5400	0.0729	0.096*
N28C	1.4553 (4)	0.64662 (19)	0.09998 (13)	0.0913 (10)
C28B	1.3339 (6)	0.6496 (2)	0.13141 (16)	0.1047 (16)
H28D	1.2941	0.7015	0.1437	0.126*
N28B	1.2732 (4)	0.57561 (17)	0.14415 (13)	0.0927 (10)
O3A	0.2407 (3)	−0.10679 (15)	0.04757 (9)	0.0766 (6)
C3A	0.1539 (4)	−0.1536 (2)	0.08194 (17)	0.0746 (9)
C3B	0.0438 (5)	−0.2023 (3)	0.0477 (2)	0.1178 (17)
H3B1	−0.0081	−0.2405	0.0731	0.177*
H3B2	0.0916	−0.2350	0.0178	0.177*
H3B3	−0.0231	−0.1627	0.0300	0.177*
O3B	0.1642 (3)	−0.15572 (16)	0.13343 (11)	0.0893 (7)
C23	0.2444 (4)	0.0802 (2)	0.04879 (15)	0.0751 (9)
H23A	0.1617	0.0470	0.0367	0.113*
H23B	0.2525	0.1305	0.0247	0.113*
H23C	0.2326	0.0972	0.0888	0.113*
C24	0.4052 (4)	0.0100 (2)	−0.02329 (11)	0.0722 (9)
H24A	0.4741	−0.0357	−0.0287	0.108*
H24B	0.4413	0.0616	−0.0411	0.108*
H24C	0.3145	−0.0057	−0.0410	0.108*

	U11	U22	U33	U12	U13	U23
C1	0.0710 (18)	0.0417 (12)	0.0609 (14)	−0.0054 (13)	−0.0163 (14)	0.0070 (11)
C2	0.081 (2)	0.0515 (15)	0.0729 (18)	−0.0131 (16)	−0.0204 (17)	0.0042 (13)
C3	0.0663 (18)	0.0673 (17)	0.0506 (13)	−0.0177 (15)	−0.0091 (13)	−0.0030 (12)
C4	0.0584 (16)	0.0628 (16)	0.0450 (12)	0.0015 (14)	−0.0051 (12)	0.0002 (11)
C5	0.0529 (14)	0.0493 (13)	0.0391 (11)	0.0029 (12)	−0.0007 (11)	0.0023 (10)
C6	0.0595 (17)	0.0511 (15)	0.0585 (14)	0.0087 (13)	−0.0062 (13)	0.0123 (12)
C7	0.0610 (16)	0.0405 (12)	0.0653 (15)	0.0070 (13)	−0.0060 (14)	0.0056 (11)
C8	0.0538 (15)	0.0354 (11)	0.0446 (11)	0.0047 (10)	0.0025 (11)	0.0067 (9)
C26	0.0673 (17)	0.0485 (13)	0.0486 (12)	−0.0040 (13)	0.0025 (13)	0.0091 (11)
C9	0.0534 (14)	0.0369 (10)	0.0395 (10)	0.0001 (11)	0.0002 (10)	0.0067 (8)
C10	0.0555 (14)	0.0405 (11)	0.0435 (11)	0.0016 (11)	−0.0033 (11)	0.0037 (10)
C25	0.0696 (19)	0.0622 (16)	0.0521 (13)	0.0051 (15)	0.0017 (13)	−0.0098 (12)
C11	0.0582 (15)	0.0324 (11)	0.0599 (13)	0.0004 (11)	−0.0062 (13)	0.0073 (10)
C12	0.0591 (16)	0.0415 (12)	0.0588 (14)	−0.0021 (12)	−0.0110 (12)	0.0105 (11)
C13	0.0557 (15)	0.0379 (11)	0.0460 (12)	−0.0008 (11)	0.0006 (11)	0.0022 (9)
C14	0.0564 (15)	0.0370 (11)	0.0483 (12)	0.0012 (11)	0.0037 (12)	−0.0003 (9)
C27	0.0609 (17)	0.0701 (18)	0.0546 (14)	0.0003 (15)	0.0088 (14)	−0.0073 (13)
C15	0.0696 (19)	0.0367 (12)	0.0749 (17)	0.0053 (13)	0.0024 (15)	−0.0028 (11)
C16	0.076 (2)	0.0424 (13)	0.0772 (18)	0.0000 (15)	0.0019 (16)	−0.0104 (13)
C17	0.0673 (17)	0.0403 (12)	0.0601 (14)	−0.0046 (13)	0.0043 (14)	−0.0102 (11)
C18	0.0617 (16)	0.0449 (13)	0.0472 (12)	−0.0054 (12)	0.0026 (12)	−0.0011 (10)
C19	0.0613 (16)	0.0541 (14)	0.0542 (13)	−0.0044 (13)	−0.0046 (13)	−0.0018 (11)
C21	0.075 (2)	0.0687 (19)	0.083 (2)	−0.0126 (17)	−0.0129 (18)	−0.0126 (16)
C22	0.084 (2)	0.0630 (17)	0.0735 (18)	−0.0137 (17)	−0.0030 (17)	−0.0216 (15)
O28B	0.115 (2)	0.0569 (14)	0.178 (3)	0.0232 (15)	0.069 (2)	0.0178 (16)
O28A	0.0707 (14)	0.0390 (9)	0.1026 (15)	−0.0049 (9)	0.0170 (12)	0.0013 (9)
C28	0.077 (2)	0.0369 (12)	0.0758 (18)	−0.0084 (13)	0.0056 (15)	−0.0017 (12)
C28A	0.0659 (18)	0.0434 (13)	0.0644 (15)	0.0007 (14)	0.0034 (14)	0.0015 (12)
C30	0.109 (3)	0.129 (3)	0.0663 (19)	−0.016 (3)	−0.009 (2)	0.029 (2)
C29	0.114 (3)	0.071 (2)	0.095 (3)	0.005 (2)	−0.026 (2)	0.0128 (19)
C20	0.078 (2)	0.0687 (18)	0.0573 (15)	−0.0102 (17)	−0.0224 (15)	0.0064 (13)
N28A	0.0686 (15)	0.0433 (11)	0.0534 (11)	−0.0037 (11)	0.0010 (11)	0.0030 (9)
C28C	0.077 (2)	0.069 (2)	0.095 (2)	−0.0130 (19)	0.0108 (19)	0.0151 (17)
N28C	0.129 (3)	0.0584 (16)	0.0869 (19)	−0.0260 (19)	0.008 (2)	0.0077 (14)
C28B	0.184 (5)	0.0436 (16)	0.087 (2)	−0.004 (2)	0.043 (3)	−0.0026 (15)
N28B	0.132 (3)	0.0465 (13)	0.099 (2)	0.0014 (17)	0.050 (2)	−0.0007 (14)
O3A	0.0812 (15)	0.0842 (15)	0.0645 (12)	−0.0263 (13)	−0.0180 (12)	0.0007 (11)
C3A	0.074 (2)	0.0611 (18)	0.088 (2)	−0.0109 (17)	−0.0110 (19)	0.0049 (17)
C3B	0.117 (4)	0.106 (3)	0.130 (3)	−0.053 (3)	−0.046 (3)	0.017 (3)
O3B	0.0966 (18)	0.0872 (16)	0.0840 (16)	−0.0238 (15)	−0.0001 (14)	0.0063 (13)
C23	0.0578 (18)	0.084 (2)	0.083 (2)	0.0057 (18)	−0.0044 (17)	−0.0024 (17)
C24	0.078 (2)	0.093 (2)	0.0453 (13)	−0.0016 (19)	−0.0126 (14)	−0.0007 (14)

C1—C2	1.527 (4)	C15—H15A	0.9700
C1—C10	1.545 (3)	C15—H15B	0.9700
C1—H1A	0.9700	C16—C17	1.518 (4)
C1—H1B	0.9700	C16—H16A	0.9700
C2—C3	1.510 (4)	C16—H16B	0.9700
C2—H2A	0.9700	C17—C28	1.525 (4)
C2—H2B	0.9700	C17—C22	1.526 (4)
C3—O3A	1.468 (3)	C17—C18	1.549 (3)
C3—C4	1.528 (4)	C18—C19	1.538 (4)
C3—H3	0.9800	C18—H18	0.9800
C4—C23	1.533 (4)	C19—C20	1.514 (4)
C4—C24	1.545 (4)	C19—C21	1.570 (4)
C4—C5	1.550 (4)	C19—H19	0.9800
C5—C6	1.534 (4)	C21—C22	1.530 (5)
C5—C10	1.557 (3)	C21—H21A	0.9700
C5—H5	0.9800	C21—H21B	0.9700
C6—C7	1.524 (4)	C22—H22A	0.9700
C6—H6A	0.9700	C22—H22B	0.9700
C6—H6B	0.9700	O28B—C28A	1.179 (4)
C7—C8	1.536 (4)	O28A—C28A	1.290 (3)
C7—H7A	0.9700	O28A—C28	1.461 (3)
C7—H7B	0.9700	C28—H28A	0.9700
C8—C26	1.545 (3)	C28—H28B	0.9700
C8—C9	1.566 (3)	C28A—N28A	1.405 (3)
C8—C14	1.588 (3)	C30—C20	1.467 (5)
C26—H26A	0.9600	C30—H30A	0.9600
C26—H26B	0.9600	C30—H30B	0.9600
C26—H26C	0.9600	C30—H30C	0.9600
C9—C11	1.528 (3)	C29—C20	1.330 (5)
C9—C10	1.567 (3)	C29—H29A	0.9300
C9—H9	0.9800	C29—H29B	0.9300
C10—C25	1.541 (4)	N28A—N28B	1.343 (3)
C25—H25A	0.9600	N28A—C28C	1.346 (4)
C25—H25B	0.9600	C28C—N28C	1.292 (5)
C25—H25C	0.9600	C28C—H28C	0.9300
C11—C12	1.520 (3)	N28C—C28B	1.331 (6)
C11—H11A	0.9700	C28B—N28B	1.311 (4)
C11—H11B	0.9700	C28B—H28D	0.9300
C12—C13	1.527 (3)	O3A—C3A	1.337 (4)
C12—H12A	0.9700	C3A—O3B	1.185 (4)
C12—H12B	0.9700	C3A—C3B	1.489 (5)
C13—C18	1.527 (3)	C3B—H3B1	0.9600
C13—C14	1.562 (4)	C3B—H3B2	0.9600
C13—H13	0.9800	C3B—H3B3	0.9600
C14—C27	1.551 (4)	C23—H23A	0.9600
C14—C15	1.557 (3)	C23—H23B	0.9600
C27—H27A	0.9600	C23—H23C	0.9600
C27—H27B	0.9600	C24—H24A	0.9600
C27—H27C	0.9600	C24—H24B	0.9600
C15—C16	1.529 (4)	C24—H24C	0.9600
C2—C1—C10	114.0 (2)	C16—C15—C14	115.0 (2)
C2—C1—H1A	108.8	C16—C15—H15A	108.5
C10—C1—H1A	108.8	C14—C15—H15A	108.5
C2—C1—H1B	108.8	C16—C15—H15B	108.5
C10—C1—H1B	108.8	C14—C15—H15B	108.5
H1A—C1—H1B	107.7	H15A—C15—H15B	107.5
C3—C2—C1	110.2 (2)	C17—C16—C15	111.3 (2)
C3—C2—H2A	109.6	C17—C16—H16A	109.4
C1—C2—H2A	109.6	C15—C16—H16A	109.4
C3—C2—H2B	109.6	C17—C16—H16B	109.4
C1—C2—H2B	109.6	C15—C16—H16B	109.4
H2A—C2—H2B	108.1	H16A—C16—H16B	108.0
O3A—C3—C2	108.8 (2)	C16—C17—C28	110.6 (2)
O3A—C3—C4	108.9 (2)	C16—C17—C22	116.7 (2)
C2—C3—C4	114.1 (2)	C28—C17—C22	108.9 (2)
O3A—C3—H3	108.3	C16—C17—C18	109.2 (2)
C2—C3—H3	108.3	C28—C17—C18	110.7 (2)
C4—C3—H3	108.3	C22—C17—C18	100.2 (2)
C3—C4—C23	108.0 (2)	C13—C18—C19	120.4 (2)
C3—C4—C24	111.8 (2)	C13—C18—C17	112.6 (2)
C23—C4—C24	106.9 (2)	C19—C18—C17	104.1 (2)
C3—C4—C5	105.3 (2)	C13—C18—H18	106.3
C23—C4—C5	109.5 (2)	C19—C18—H18	106.3
C24—C4—C5	115.1 (2)	C17—C18—H18	106.3
C6—C5—C4	114.7 (2)	C20—C19—C18	117.7 (3)
C6—C5—C10	110.7 (2)	C20—C19—C21	111.7 (2)
C4—C5—C10	117.4 (2)	C18—C19—C21	103.0 (2)
C6—C5—H5	104.1	C20—C19—H19	108.0
C4—C5—H5	104.1	C18—C19—H19	108.0
C10—C5—H5	104.1	C21—C19—H19	108.0
C7—C6—C5	110.5 (2)	C22—C21—C19	106.5 (2)
C7—C6—H6A	109.5	C22—C21—H21A	110.4
C5—C6—H6A	109.5	C19—C21—H21A	110.4
C7—C6—H6B	109.5	C22—C21—H21B	110.4
C5—C6—H6B	109.5	C19—C21—H21B	110.4
H6A—C6—H6B	108.1	H21A—C21—H21B	108.6
C6—C7—C8	113.9 (2)	C17—C22—C21	105.0 (2)
C6—C7—H7A	108.8	C17—C22—H22A	110.7
C8—C7—H7A	108.8	C21—C22—H22A	110.7
C6—C7—H7B	108.8	C17—C22—H22B	110.7
C8—C7—H7B	108.8	C21—C22—H22B	110.7
H7A—C7—H7B	107.7	H22A—C22—H22B	108.8
C7—C8—C26	106.7 (2)	C28A—O28A—C28	117.5 (2)
C7—C8—C9	109.0 (2)	O28A—C28—C17	106.6 (2)
C26—C8—C9	111.94 (19)	O28A—C28—H28A	110.4
C7—C8—C14	110.99 (19)	C17—C28—H28A	110.4
C26—C8—C14	110.1 (2)	O28A—C28—H28B	110.4
C9—C8—C14	108.12 (17)	C17—C28—H28B	110.4
C8—C26—H26A	109.5	H28A—C28—H28B	108.6
C8—C26—H26B	109.5	O28B—C28A—O28A	127.5 (3)
H26A—C26—H26B	109.5	O28B—C28A—N28A	120.8 (3)
C8—C26—H26C	109.5	O28A—C28A—N28A	111.5 (3)
H26A—C26—H26C	109.5	C20—C30—H30A	109.5
H26B—C26—H26C	109.5	C20—C30—H30B	109.5
C11—C9—C8	110.6 (2)	H30A—C30—H30B	109.5
C11—C9—C10	113.82 (19)	C20—C30—H30C	109.5
C8—C9—C10	117.10 (18)	H30A—C30—H30C	109.5
C11—C9—H9	104.6	H30B—C30—H30C	109.5
C8—C9—H9	104.6	C20—C29—H29A	120.0
C10—C9—H9	104.6	C20—C29—H29B	120.0
C25—C10—C1	108.2 (2)	H29A—C29—H29B	120.0
C25—C10—C5	114.2 (2)	C29—C20—C30	121.6 (3)
C1—C10—C5	107.0 (2)	C29—C20—C19	119.9 (3)
C25—C10—C9	112.1 (2)	C30—C20—C19	118.4 (3)
C1—C10—C9	107.77 (18)	N28B—N28A—C28C	108.8 (3)
C5—C10—C9	107.30 (19)	N28B—N28A—C28A	124.5 (3)
C10—C25—H25A	109.5	C28C—N28A—C28A	126.7 (3)
C10—C25—H25B	109.5	N28C—C28C—N28A	111.3 (3)
H25A—C25—H25B	109.5	N28A—C28C—C28B	71.5 (2)
C10—C25—H25C	109.5	N28C—C28C—H28C	124.4
H25A—C25—H25C	109.5	N28A—C28C—H28C	124.4
H25B—C25—H25C	109.5	C28B—C28C—H28C	164.2
C12—C11—C9	113.2 (2)	C28C—N28C—C28B	101.8 (3)
C12—C11—H11A	108.9	N28B—C28B—N28C	116.7 (3)
C9—C11—H11A	108.9	N28B—C28B—C28C	78.3 (2)
C12—C11—H11B	108.9	N28B—C28B—H28D	121.7
C9—C11—H11B	108.9	N28C—C28B—H28D	121.7
H11A—C11—H11B	107.8	C28C—C28B—H28D	160.0
C11—C12—C13	112.0 (2)	C28B—N28B—N28A	101.4 (3)
C11—C12—H12A	109.2	C3A—O3A—C3	117.3 (2)
C13—C12—H12A	109.2	O3B—C3A—O3A	123.7 (3)
C11—C12—H12B	109.2	O3B—C3A—C3B	124.5 (4)
C13—C12—H12B	109.2	O3A—C3A—C3B	111.9 (3)
H12A—C12—H12B	107.9	C3A—C3B—H3B1	109.5
C18—C13—C12	114.1 (2)	C3A—C3B—H3B2	109.5
C18—C13—C14	111.80 (19)	H3B1—C3B—H3B2	109.5
C12—C13—C14	110.7 (2)	C3A—C3B—H3B3	109.5
C18—C13—H13	106.6	H3B1—C3B—H3B3	109.5
C12—C13—H13	106.6	H3B2—C3B—H3B3	109.5
C14—C13—H13	106.6	C4—C23—H23A	109.5
C27—C14—C15	105.7 (2)	C4—C23—H23B	109.5
C27—C14—C13	109.8 (2)	H23A—C23—H23B	109.5
C15—C14—C13	109.9 (2)	C4—C23—H23C	109.5
C27—C14—C8	111.9 (2)	H23A—C23—H23C	109.5
C15—C14—C8	111.42 (19)	H23B—C23—H23C	109.5
C13—C14—C8	108.10 (18)	C4—C24—H24A	109.5
C14—C27—H27A	109.5	C4—C24—H24B	109.5
C14—C27—H27B	109.5	H24A—C24—H24B	109.5
H27A—C27—H27B	109.5	C4—C24—H24C	109.5
C14—C27—H27C	109.5	H24A—C24—H24C	109.5
H27A—C27—H27C	109.5	H24B—C24—H24C	109.5
H27B—C27—H27C	109.5
C10—C1—C2—C3	−55.5 (3)	C26—C8—C14—C13	−61.4 (2)
C1—C2—C3—O3A	−179.0 (2)	C9—C8—C14—C13	61.2 (2)
C1—C2—C3—C4	59.2 (3)	C27—C14—C15—C16	69.1 (3)
O3A—C3—C4—C23	64.5 (3)	C13—C14—C15—C16	−49.3 (3)
C2—C3—C4—C23	−173.7 (2)	C8—C14—C15—C16	−169.1 (2)
O3A—C3—C4—C24	−52.9 (3)	C14—C15—C16—C17	54.0 (3)
C2—C3—C4—C24	68.9 (3)	C15—C16—C17—C28	65.9 (3)
O3A—C3—C4—C5	−178.6 (2)	C15—C16—C17—C22	−168.9 (2)
C2—C3—C4—C5	−56.8 (3)	C15—C16—C17—C18	−56.2 (3)
C3—C4—C5—C6	−171.9 (2)	C12—C13—C18—C19	53.6 (3)
C23—C4—C5—C6	−56.1 (3)	C14—C13—C18—C19	−179.8 (2)
C24—C4—C5—C6	64.4 (3)	C12—C13—C18—C17	177.0 (2)
C3—C4—C5—C10	55.5 (3)	C14—C13—C18—C17	−56.3 (3)
C23—C4—C5—C10	171.3 (2)	C16—C17—C18—C13	59.0 (3)
C24—C4—C5—C10	−68.2 (3)	C28—C17—C18—C13	−63.0 (3)
C4—C5—C6—C7	162.3 (2)	C22—C17—C18—C13	−177.9 (2)
C10—C5—C6—C7	−62.0 (3)	C16—C17—C18—C19	−168.9 (2)
C5—C6—C7—C8	58.4 (3)	C28—C17—C18—C19	69.1 (3)
C6—C7—C8—C26	71.6 (3)	C22—C17—C18—C19	−45.8 (3)
C6—C7—C8—C9	−49.5 (3)	C13—C18—C19—C20	−76.5 (3)
C6—C7—C8—C14	−168.4 (2)	C17—C18—C19—C20	156.1 (2)
C7—C8—C9—C11	−179.3 (2)	C13—C18—C19—C21	160.1 (2)
C26—C8—C9—C11	62.9 (3)	C17—C18—C19—C21	32.7 (3)
C14—C8—C9—C11	−58.6 (2)	C20—C19—C21—C22	−134.6 (3)
C7—C8—C9—C10	48.0 (3)	C18—C19—C21—C22	−7.3 (3)
C26—C8—C9—C10	−69.8 (3)	C16—C17—C22—C21	158.4 (3)
C14—C8—C9—C10	168.74 (19)	C28—C17—C22—C21	−75.6 (3)
C2—C1—C10—C25	−72.6 (3)	C18—C17—C22—C21	40.7 (3)
C2—C1—C10—C5	50.9 (3)	C19—C21—C22—C17	−21.1 (3)
C2—C1—C10—C9	166.0 (2)	C28A—O28A—C28—C17	149.6 (3)
C6—C5—C10—C25	−67.9 (3)	C16—C17—C28—O28A	61.9 (3)
C4—C5—C10—C25	66.5 (3)	C22—C17—C28—O28A	−67.6 (3)
C6—C5—C10—C1	172.46 (19)	C18—C17—C28—O28A	−176.9 (2)
C4—C5—C10—C1	−53.2 (3)	C28—O28A—C28A—O28B	6.8 (5)
C6—C5—C10—C9	57.0 (2)	C28—O28A—C28A—N28A	−176.9 (2)
C4—C5—C10—C9	−168.60 (19)	C18—C19—C20—C29	133.8 (3)
C11—C9—C10—C25	−57.1 (3)	C21—C19—C20—C29	−107.4 (3)
C8—C9—C10—C25	74.1 (3)	C18—C19—C20—C30	−48.4 (4)
C11—C9—C10—C1	61.8 (3)	C21—C19—C20—C30	70.5 (4)
C8—C9—C10—C1	−167.0 (2)	O28B—C28A—N28A—N28B	179.7 (3)
C11—C9—C10—C5	176.71 (18)	O28A—C28A—N28A—N28B	3.1 (4)
C8—C9—C10—C5	−52.1 (3)	O28B—C28A—N28A—C28C	−0.1 (5)
C8—C9—C11—C12	54.8 (3)	O28A—C28A—N28A—C28C	−176.6 (3)
C10—C9—C11—C12	−170.86 (19)	N28B—N28A—C28C—N28C	0.4 (4)
C9—C11—C12—C13	−53.1 (3)	C28A—N28A—C28C—N28C	−179.8 (3)
C11—C12—C13—C18	−177.0 (2)	N28B—N28A—C28C—C28B	0.6 (3)
C11—C12—C13—C14	55.8 (3)	C28A—N28A—C28C—C28B	−179.6 (3)
C18—C13—C14—C27	−66.3 (3)	N28A—C28C—N28C—C28B	0.2 (4)
C12—C13—C14—C27	62.2 (3)	C28C—N28C—C28B—N28B	−0.9 (5)
C18—C13—C14—C15	49.6 (3)	N28C—C28C—C28B—N28B	179.2 (5)
C12—C13—C14—C15	178.0 (2)	N28A—C28C—C28B—N28B	−0.6 (3)
C18—C13—C14—C8	171.36 (18)	N28A—C28C—C28B—N28C	−179.8 (4)
C12—C13—C14—C8	−60.2 (2)	N28C—C28B—N28B—N28A	1.1 (5)
C7—C8—C14—C27	59.5 (3)	C28C—C28B—N28B—N28A	0.6 (3)
C26—C8—C14—C27	177.5 (2)	C28C—N28A—N28B—C28B	−0.9 (4)
C9—C8—C14—C27	−59.9 (3)	C28A—N28A—N28B—C28B	179.3 (3)
C7—C8—C14—C15	−58.5 (3)	C2—C3—O3A—C3A	89.2 (3)
C26—C8—C14—C15	59.4 (3)	C4—C3—O3A—C3A	−145.8 (3)
C9—C8—C14—C15	−178.0 (2)	C3—O3A—C3A—O3B	2.5 (5)
C7—C8—C14—C13	−179.37 (19)	C3—O3A—C3A—C3B	−177.4 (3)