(6S,7S,8S,8aS)-6-Ethyl-3-oxo-1,2,3,5,6,7,8,8a-octa-hydro-indolizine-7,8-diyl diacetate.

In the mol-ecular structure of the title compound, C(14)H(21)NO(5), the six-membered ring of the indolizine moiety adopts a chair conformation. There are two independent mol-ecules in the asymmetric unit. The oxopyrrolidine ring attached to the indolizine ring system is nearly planar, with mean deviations of 0.018 (3) and 0.010 (3) Å for the two mol-ecules. The absolute configuration of the title compound was assigned from the synthesis.

Related literature

For indolizine derivatives, see: Gubin et al. (1992 ▶); Gupta et al. (2003 ▶); Liu et al. (2007 ▶); Medda et al. (2003 ▶); Molyneux & James (1982 ▶); Nash et al. (1988 ▶); Pearson & Guo (2001 ▶); Ruprecht et al. (1989 ▶); Smith et al. (2007 ▶); Teklu et al. (2005 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For the synthesis, see: Šafář et al. (2010 ▶). For related structures, see: Brown & Corbridge (1954 ▶); Pedersen (1967 ▶).

Experimental

Crystal data

C14H21NO5

M = 283.32

Monoclinic,

a = 11.5157 (2) Å

b = 9.8239 (1) Å

c = 14.0922 (2) Å

β = 99.035 (2)°

V = 1574.46 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.40 × 0.30 × 0.20 mm

Data collection

Oxford Diffraction Gemini R CCD diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.952, T max = 0.984

37222 measured reflections

3404 independent reflections

2508 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.104

S = 1.03

3404 reflections

361 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.11 e Å−3

Δρmin = −0.14 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2001 ▶); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009 ▶) and WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812005144/bq2336sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812005144/bq2336Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812005144/bq2336Isup3.cml

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

C14H21NO5	F(000) = 608
Mr = 283.32	Dx = 1.195 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 37222 reflections
a = 11.5157 (2) Å	θ = 4.1–26.4°
b = 9.8239 (1) Å	µ = 0.09 mm−1
c = 14.0922 (2) Å	T = 298 K
β = 99.035 (2)°	Prism, colourless
V = 1574.46 (4) Å3	0.40 × 0.30 × 0.20 mm
Z = 4

Oxford Diffraction Gemini R CCD diffractometer	3404 independent reflections
Radiation source: fine-focus sealed tube	2508 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
Detector resolution: 10.4340 pixels mm-1	θmax = 26.4°, θmin = 4.1°
Rotation method data acquisition using ω and φ scans	h = −14→14
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −12→12
Tmin = 0.952, Tmax = 0.984	l = −17→17
37222 measured reflections

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0702P)2] where P = (Fo2 + 2Fc2)/3
3404 reflections	(Δ/σ)max < 0.001
361 parameters	Δρmax = 0.11 e Å−3
1 restraint	Δρmin = −0.14 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	Occ. (<1)
C2	0.8545 (2)	−0.0286 (3)	0.56842 (19)	0.0737 (7)
C3	0.7241 (3)	−0.0115 (3)	0.5372 (3)	0.0989 (9)
H3B	0.6979	−0.0639	0.4794	0.119*
H3A	0.6813	−0.0420	0.5873	0.119*
C4	0.7043 (3)	0.1376 (3)	0.5183 (3)	0.0889 (8)
H4B	0.6572	0.1759	0.5630	0.107*
H4A	0.6637	0.1521	0.4534	0.107*
C5	0.8254 (2)	0.2041 (2)	0.53147 (16)	0.0638 (6)
H5A	0.8418	0.2376	0.4694	0.077*
C6	0.84460 (18)	0.3181 (2)	0.60532 (14)	0.0556 (5)
H6A	0.8144	0.2913	0.6638	0.067*
C7	0.97364 (18)	0.3545 (2)	0.62885 (14)	0.0575 (5)
H7A	0.9995	0.3922	0.5712	0.069*
C8	1.05094 (19)	0.2324 (3)	0.66341 (15)	0.0631 (5)
H8A	1.1331	0.2614	0.6681	0.076*
C9	1.0288 (2)	0.1237 (3)	0.58517 (16)	0.0683 (6)
H9B	1.0561	0.1560	0.5275	0.082*
H9A	1.0722	0.0417	0.6065	0.082*
C10	0.6967 (2)	0.4880 (3)	0.60542 (19)	0.0747 (7)
C11	0.6557 (3)	0.6217 (4)	0.5632 (3)	0.1127 (11)
H11C	0.5929	0.6551	0.5942	0.169*	0.50
H11B	0.6281	0.6109	0.4957	0.169*	0.50
H11A	0.7197	0.6854	0.5724	0.169*	0.50
H11F	0.7009	0.6458	0.5140	0.169*	0.50
H11E	0.6657	0.6900	0.6125	0.169*	0.50
H11D	0.5741	0.6155	0.5359	0.169*	0.50
C12	1.0680 (2)	0.5503 (3)	0.70642 (16)	0.0670 (6)
C13	1.0580 (3)	0.6588 (3)	0.7779 (2)	0.0993 (9)
H13C	1.1180	0.7259	0.7753	0.149*	0.50
H13B	1.0673	0.6198	0.8411	0.149*	0.50
H13A	0.9821	0.7011	0.7635	0.149*	0.50
H13F	0.9935	0.6386	0.8113	0.149*	0.50
H13E	1.0443	0.7447	0.7455	0.149*	0.50
H13D	1.1295	0.6634	0.8231	0.149*	0.50
C14	1.0331 (3)	0.1806 (3)	0.76184 (18)	0.0828 (7)
H14B	1.0357	0.2573	0.8055	0.099*
H14A	0.9557	0.1399	0.7566	0.099*
C15	1.1237 (3)	0.0773 (4)	0.8039 (3)	0.1224 (13)
H15C	1.1077	0.0489	0.8657	0.184*
H15B	1.2006	0.1174	0.8107	0.184*
H15A	1.1204	−0.0001	0.7620	0.184*
C16	0.5132 (2)	0.5197 (3)	0.86454 (19)	0.0705 (6)
C17	0.4201 (2)	0.5033 (3)	0.7765 (2)	0.0829 (7)
H17B	0.3542	0.5636	0.7800	0.099*
H17A	0.4523	0.5238	0.7186	0.099*
C18	0.3821 (3)	0.3583 (3)	0.7768 (3)	0.1040 (10)
H18B	0.3932	0.3143	0.7172	0.125*
H18A	0.2996	0.3527	0.7830	0.125*
C19	0.4576 (2)	0.2884 (3)	0.86243 (18)	0.0696 (6)
H19A	0.4068	0.2543	0.9068	0.084*
C20	0.5353 (2)	0.1748 (2)	0.83702 (15)	0.0602 (5)
H20A	0.5746	0.2018	0.7831	0.072*
C21	0.6251 (2)	0.1355 (2)	0.92278 (15)	0.0629 (6)
H21A	0.5844	0.0979	0.9729	0.076*
C22	0.69956 (19)	0.2565 (3)	0.96345 (15)	0.0639 (6)
H22A	0.7486	0.2263	1.0229	0.077*
C23	0.6164 (2)	0.3658 (3)	0.99042 (16)	0.0716 (6)
H23B	0.5773	0.3333	1.0422	0.086*
H23A	0.6606	0.4469	1.0124	0.086*
C24	0.4582 (3)	0.0020 (3)	0.7247 (2)	0.0877 (8)
C25	0.3881 (4)	−0.1254 (4)	0.7148 (3)	0.1301 (14)
H25C	0.3881	−0.1631	0.6519	0.195*	0.50
H25B	0.3087	−0.1058	0.7235	0.195*	0.50
H25A	0.4220	−0.1898	0.7624	0.195*	0.50
H25F	0.3578	−0.1427	0.7733	0.195*	0.50
H25E	0.4371	−0.1999	0.7017	0.195*	0.50
H25D	0.3239	−0.1160	0.6628	0.195*	0.50
C26	0.7488 (2)	−0.0597 (3)	0.9512 (3)	0.0968 (9)
C27	0.8059 (3)	−0.1700 (4)	0.9024 (4)	0.1403 (16)
H27C	0.8445	−0.2322	0.9497	0.210*	0.50
H27B	0.8627	−0.1310	0.8673	0.210*	0.50
H27A	0.7473	−0.2178	0.8590	0.210*	0.50
H27F	0.7918	−0.1551	0.8343	0.210*	0.50
H27E	0.7737	−0.2564	0.9167	0.210*	0.50
H27D	0.8890	−0.1695	0.9250	0.210*	0.50
C28	0.7819 (2)	0.3082 (3)	0.89634 (17)	0.0788 (7)
H28B	0.8224	0.2311	0.8737	0.095*
H28A	0.7351	0.3503	0.8408	0.095*
C29	0.8716 (3)	0.4091 (5)	0.9418 (3)	0.1207 (13)
H29C	0.9133	0.4456	0.8937	0.181*
H29B	0.9260	0.3645	0.9906	0.181*
H29A	0.8328	0.4815	0.9701	0.181*
N1	0.90503 (17)	0.09344 (19)	0.56432 (13)	0.0636 (5)
N2	0.53009 (18)	0.3980 (2)	0.90770 (15)	0.0708 (5)
O1	0.9073 (2)	−0.1337 (2)	0.59263 (17)	0.1011 (6)
O2	0.78379 (13)	0.43758 (17)	0.56408 (11)	0.0666 (4)
O3	0.6567 (2)	0.4302 (3)	0.66728 (17)	0.1181 (8)
O4	0.98020 (13)	0.46046 (18)	0.70120 (10)	0.0679 (4)
O5	1.14461 (16)	0.5425 (2)	0.65819 (12)	0.0856 (5)
O6	0.56358 (19)	0.6243 (2)	0.89226 (16)	0.0923 (6)
O7	0.46121 (14)	0.05762 (17)	0.81120 (11)	0.0695 (4)
O8	0.5052 (3)	0.0493 (4)	0.66446 (17)	0.1501 (12)
O9	0.69467 (16)	0.0294 (2)	0.88760 (13)	0.0826 (5)
O10	0.7497 (2)	−0.0500 (3)	1.0360 (2)	0.1259 (9)

	U11	U22	U33	U12	U13	U23
C2	0.0872 (17)	0.0531 (15)	0.0852 (15)	0.0041 (14)	0.0269 (13)	0.0059 (12)
C3	0.0889 (19)	0.0666 (18)	0.144 (3)	−0.0067 (16)	0.0265 (18)	0.0090 (17)
C4	0.0780 (17)	0.0680 (18)	0.113 (2)	−0.0098 (15)	−0.0081 (14)	0.0068 (16)
C5	0.0670 (13)	0.0564 (13)	0.0662 (12)	−0.0004 (11)	0.0044 (10)	0.0068 (11)
C6	0.0581 (12)	0.0506 (11)	0.0591 (11)	0.0051 (10)	0.0124 (9)	0.0090 (10)
C7	0.0615 (12)	0.0580 (13)	0.0554 (11)	−0.0024 (11)	0.0163 (9)	−0.0059 (10)
C8	0.0573 (12)	0.0677 (14)	0.0644 (12)	0.0057 (12)	0.0103 (9)	−0.0040 (11)
C9	0.0692 (14)	0.0652 (14)	0.0716 (13)	0.0101 (12)	0.0145 (10)	−0.0050 (11)
C10	0.0681 (14)	0.0686 (16)	0.0875 (16)	0.0122 (13)	0.0127 (13)	−0.0018 (13)
C11	0.104 (2)	0.073 (2)	0.161 (3)	0.0268 (19)	0.022 (2)	0.007 (2)
C12	0.0729 (14)	0.0590 (14)	0.0651 (12)	−0.0023 (13)	−0.0017 (11)	0.0075 (11)
C13	0.115 (2)	0.0734 (19)	0.106 (2)	−0.0096 (17)	0.0070 (17)	−0.0213 (16)
C14	0.0967 (18)	0.0839 (18)	0.0657 (14)	0.0198 (15)	0.0066 (13)	0.0070 (13)
C15	0.118 (3)	0.116 (3)	0.124 (2)	0.016 (2)	−0.0097 (19)	0.041 (2)
C16	0.0691 (14)	0.0539 (15)	0.0925 (16)	0.0012 (12)	0.0249 (12)	−0.0094 (13)
C17	0.0702 (15)	0.0698 (17)	0.1057 (18)	0.0084 (13)	0.0048 (13)	0.0078 (14)
C18	0.101 (2)	0.0642 (17)	0.129 (2)	0.0087 (16)	−0.0360 (18)	−0.0061 (17)
C19	0.0644 (13)	0.0557 (14)	0.0862 (15)	−0.0003 (11)	0.0039 (11)	−0.0064 (12)
C20	0.0673 (13)	0.0538 (13)	0.0607 (11)	−0.0043 (11)	0.0134 (10)	0.0006 (10)
C21	0.0661 (13)	0.0633 (14)	0.0612 (12)	0.0090 (12)	0.0156 (10)	0.0058 (11)
C22	0.0646 (12)	0.0730 (16)	0.0538 (11)	0.0046 (12)	0.0084 (9)	−0.0008 (11)
C23	0.0730 (14)	0.0779 (16)	0.0642 (13)	−0.0014 (13)	0.0121 (11)	−0.0122 (12)
C24	0.105 (2)	0.0780 (19)	0.0827 (17)	−0.0088 (16)	0.0217 (15)	−0.0191 (14)
C25	0.171 (4)	0.081 (2)	0.136 (3)	−0.035 (2)	0.017 (3)	−0.043 (2)
C26	0.0648 (16)	0.0689 (19)	0.154 (3)	0.0076 (15)	0.0091 (18)	0.018 (2)
C27	0.090 (2)	0.078 (2)	0.250 (5)	0.0224 (19)	0.018 (3)	−0.022 (3)
C28	0.0731 (15)	0.0922 (19)	0.0735 (14)	−0.0126 (15)	0.0187 (11)	−0.0117 (14)
C29	0.104 (2)	0.137 (3)	0.126 (2)	−0.038 (2)	0.0343 (19)	−0.032 (3)
N1	0.0686 (11)	0.0508 (11)	0.0703 (10)	0.0038 (9)	0.0073 (9)	0.0014 (8)
N2	0.0679 (12)	0.0571 (12)	0.0838 (13)	0.0019 (10)	0.0007 (10)	−0.0106 (10)
O1	0.1129 (15)	0.0586 (11)	0.1369 (17)	0.0145 (12)	0.0351 (13)	0.0165 (12)
O2	0.0688 (9)	0.0574 (9)	0.0749 (9)	0.0083 (8)	0.0157 (7)	0.0120 (8)
O3	0.1130 (15)	0.124 (2)	0.1310 (17)	0.0431 (15)	0.0634 (14)	0.0319 (16)
O4	0.0733 (9)	0.0625 (10)	0.0704 (8)	−0.0020 (9)	0.0185 (7)	−0.0114 (8)
O5	0.0793 (10)	0.0915 (13)	0.0853 (10)	−0.0186 (10)	0.0109 (9)	0.0003 (10)
O6	0.0981 (13)	0.0630 (12)	0.1168 (14)	−0.0122 (11)	0.0203 (11)	−0.0161 (11)
O7	0.0800 (10)	0.0554 (9)	0.0749 (9)	−0.0086 (8)	0.0177 (7)	−0.0080 (8)
O8	0.203 (3)	0.169 (3)	0.0902 (13)	−0.078 (3)	0.0596 (16)	−0.0421 (18)
O9	0.0816 (11)	0.0694 (11)	0.0993 (11)	0.0176 (10)	0.0223 (9)	−0.0020 (10)
O10	0.1194 (18)	0.112 (2)	0.1410 (19)	0.0225 (16)	0.0056 (15)	0.0507 (19)

C2—O1	1.220 (3)	C16—O6	1.214 (3)
C2—N1	1.338 (3)	C16—N2	1.342 (4)
C2—C3	1.506 (4)	C16—C17	1.515 (4)
C3—C4	1.500 (5)	C17—C18	1.490 (4)
C3—H3B	0.9700	C17—H17B	0.9700
C3—H3A	0.9700	C17—H17A	0.9700
C4—C5	1.525 (4)	C18—C19	1.534 (4)
C4—H4B	0.9700	C18—H18B	0.9700
C4—H4A	0.9700	C18—H18A	0.9700
C5—N1	1.451 (3)	C19—N2	1.448 (3)
C5—C6	1.521 (3)	C19—C20	1.509 (3)
C5—H5A	0.9800	C19—H19A	0.9800
C6—O2	1.441 (3)	C20—O7	1.445 (3)
C6—C7	1.514 (3)	C20—C21	1.512 (3)
C6—H6A	0.9800	C20—H20A	0.9800
C7—O4	1.450 (3)	C21—O9	1.449 (3)
C7—C8	1.527 (3)	C21—C22	1.524 (3)
C7—H7A	0.9800	C21—H21A	0.9800
C8—C14	1.521 (4)	C22—C23	1.527 (3)
C8—C9	1.528 (3)	C22—C28	1.527 (3)
C8—H8A	0.9800	C22—H22A	0.9800
C9—N1	1.441 (3)	C23—N2	1.443 (3)
C9—H9B	0.9700	C23—H23B	0.9700
C9—H9A	0.9700	C23—H23A	0.9700
C10—O3	1.192 (3)	C24—O8	1.172 (4)
C10—O2	1.332 (3)	C24—O7	1.331 (3)
C10—C11	1.488 (4)	C24—C25	1.484 (5)
C11—H11C	0.9600	C25—H25C	0.9600
C11—H11B	0.9600	C25—H25B	0.9600
C11—H11A	0.9600	C25—H25A	0.9600
C11—H11F	0.9600	C25—H25F	0.9600
C11—H11E	0.9600	C25—H25E	0.9600
C11—H11D	0.9600	C25—H25D	0.9600
C12—O5	1.197 (3)	C26—O10	1.198 (4)
C12—O4	1.336 (3)	C26—O9	1.335 (4)
C12—C13	1.483 (4)	C26—C27	1.490 (5)
C13—H13C	0.9600	C27—H27C	0.9600
C13—H13B	0.9600	C27—H27B	0.9600
C13—H13A	0.9600	C27—H27A	0.9600
C13—H13F	0.9600	C27—H27F	0.9600
C13—H13E	0.9600	C27—H27E	0.9600
C13—H13D	0.9600	C27—H27D	0.9600
C14—C15	1.508 (5)	C28—C29	1.500 (5)
C14—H14B	0.9700	C28—H28B	0.9700
C14—H14A	0.9700	C28—H28A	0.9700
C15—H15C	0.9600	C29—H29C	0.9600
C15—H15B	0.9600	C29—H29B	0.9600
C15—H15A	0.9600	C29—H29A	0.9600
O1—C2—N1	124.7 (2)	C16—C17—H17B	110.6
O1—C2—C3	127.3 (2)	C18—C17—H17A	110.6
N1—C2—C3	108.0 (2)	C16—C17—H17A	110.6
C4—C3—C2	106.1 (2)	H17B—C17—H17A	108.7
C4—C3—H3B	110.5	C17—C18—C19	107.4 (2)
C2—C3—H3B	110.5	C17—C18—H18B	110.2
C4—C3—H3A	110.5	C19—C18—H18B	110.2
C2—C3—H3A	110.5	C17—C18—H18A	110.2
H3B—C3—H3A	108.7	C19—C18—H18A	110.2
C3—C4—C5	106.7 (2)	H18B—C18—H18A	108.5
C3—C4—H4B	110.4	N2—C19—C20	109.42 (18)
C5—C4—H4B	110.4	N2—C19—C18	103.3 (2)
C3—C4—H4A	110.4	C20—C19—C18	115.3 (2)
C5—C4—H4A	110.4	N2—C19—H19A	109.5
H4B—C4—H4A	108.6	C20—C19—H19A	109.5
N1—C5—C6	108.47 (17)	C18—C19—H19A	109.5
N1—C5—C4	103.7 (2)	O7—C20—C19	107.49 (17)
C6—C5—C4	115.5 (2)	O7—C20—C21	107.50 (18)
N1—C5—H5A	109.6	C19—C20—C21	110.83 (18)
C6—C5—H5A	109.6	O7—C20—H20A	110.3
C4—C5—H5A	109.6	C19—C20—H20A	110.3
O2—C6—C7	107.10 (17)	C21—C20—H20A	110.3
O2—C6—C5	108.32 (15)	O9—C21—C20	104.81 (18)
C7—C6—C5	110.86 (17)	O9—C21—C22	112.40 (17)
O2—C6—H6A	110.2	C20—C21—C22	112.06 (19)
C7—C6—H6A	110.2	O9—C21—H21A	109.1
C5—C6—H6A	110.2	C20—C21—H21A	109.1
O4—C7—C6	105.33 (16)	C22—C21—H21A	109.1
O4—C7—C8	112.09 (16)	C21—C22—C23	107.71 (18)
C6—C7—C8	112.78 (18)	C21—C22—C28	113.21 (18)
O4—C7—H7A	108.8	C23—C22—C28	113.2 (2)
C6—C7—H7A	108.8	C21—C22—H22A	107.5
C8—C7—H7A	108.8	C23—C22—H22A	107.5
C14—C8—C7	113.47 (19)	C28—C22—H22A	107.5
C14—C8—C9	113.1 (2)	N2—C23—C22	109.41 (18)
C7—C8—C9	107.24 (16)	N2—C23—H23B	109.8
C14—C8—H8A	107.6	C22—C23—H23B	109.8
C7—C8—H8A	107.6	N2—C23—H23A	109.8
C9—C8—H8A	107.6	C22—C23—H23A	109.8
N1—C9—C8	109.81 (18)	H23B—C23—H23A	108.2
N1—C9—H9B	109.7	O8—C24—O7	123.5 (3)
C8—C9—H9B	109.7	O8—C24—C25	124.9 (3)
N1—C9—H9A	109.7	O7—C24—C25	111.6 (3)
C8—C9—H9A	109.7	C24—C25—H25C	109.5
H9B—C9—H9A	108.2	C24—C25—H25B	109.5
O3—C10—O2	123.1 (2)	H25C—C25—H25B	109.5
O3—C10—C11	125.4 (3)	C24—C25—H25A	109.5
O2—C10—C11	111.5 (3)	H25C—C25—H25A	109.5
C10—C11—H11C	109.5	H25B—C25—H25A	109.5
C10—C11—H11B	109.5	C24—C25—H25F	109.5
H11C—C11—H11B	109.5	H25C—C25—H25F	141.1
C10—C11—H11A	109.5	H25B—C25—H25F	56.3
H11C—C11—H11A	109.5	H25A—C25—H25F	56.3
H11B—C11—H11A	109.5	C24—C25—H25E	109.5
C10—C11—H11F	109.5	H25C—C25—H25E	56.3
H11C—C11—H11F	141.1	H25B—C25—H25E	141.1
H11B—C11—H11F	56.3	H25A—C25—H25E	56.3
H11A—C11—H11F	56.3	H25F—C25—H25E	109.5
C10—C11—H11E	109.5	C24—C25—H25D	109.5
H11C—C11—H11E	56.3	H25C—C25—H25D	56.3
H11B—C11—H11E	141.1	H25B—C25—H25D	56.3
H11A—C11—H11E	56.3	H25A—C25—H25D	141.1
H11F—C11—H11E	109.5	H25F—C25—H25D	109.5
C10—C11—H11D	109.5	H25E—C25—H25D	109.5
H11C—C11—H11D	56.3	O10—C26—O9	123.2 (3)
H11B—C11—H11D	56.3	O10—C26—C27	125.6 (4)
H11A—C11—H11D	141.1	O9—C26—C27	111.1 (4)
H11F—C11—H11D	109.5	C26—C27—H27C	109.5
H11E—C11—H11D	109.5	C26—C27—H27B	109.5
O5—C12—O4	123.0 (2)	H27C—C27—H27B	109.5
O5—C12—C13	125.1 (3)	C26—C27—H27A	109.5
O4—C12—C13	111.9 (2)	H27C—C27—H27A	109.5
C12—C13—H13C	109.5	H27B—C27—H27A	109.5
C12—C13—H13B	109.5	C26—C27—H27F	109.5
H13C—C13—H13B	109.5	H27C—C27—H27F	141.1
C12—C13—H13A	109.5	H27B—C27—H27F	56.3
H13C—C13—H13A	109.5	H27A—C27—H27F	56.3
H13B—C13—H13A	109.5	C26—C27—H27E	109.5
C12—C13—H13F	109.5	H27C—C27—H27E	56.3
H13C—C13—H13F	141.1	H27B—C27—H27E	141.1
H13B—C13—H13F	56.3	H27A—C27—H27E	56.3
H13A—C13—H13F	56.3	H27F—C27—H27E	109.5
C12—C13—H13E	109.5	C26—C27—H27D	109.5
H13C—C13—H13E	56.3	H27C—C27—H27D	56.3
H13B—C13—H13E	141.1	H27B—C27—H27D	56.3
H13A—C13—H13E	56.3	H27A—C27—H27D	141.1
H13F—C13—H13E	109.5	H27F—C27—H27D	109.5
C12—C13—H13D	109.5	H27E—C27—H27D	109.5
H13C—C13—H13D	56.3	C29—C28—C22	114.1 (2)
H13B—C13—H13D	56.3	C29—C28—H28B	108.7
H13A—C13—H13D	141.1	C22—C28—H28B	108.7
H13F—C13—H13D	109.5	C29—C28—H28A	108.7
H13E—C13—H13D	109.5	C22—C28—H28A	108.7
C15—C14—C8	113.6 (3)	H28B—C28—H28A	107.6
C15—C14—H14B	108.9	C28—C29—H29C	109.5
C8—C14—H14B	108.9	C28—C29—H29B	109.5
C15—C14—H14A	108.9	H29C—C29—H29B	109.5
C8—C14—H14A	108.9	C28—C29—H29A	109.5
H14B—C14—H14A	107.7	H29C—C29—H29A	109.5
C14—C15—H15C	109.5	H29B—C29—H29A	109.5
C14—C15—H15B	109.5	C2—N1—C9	126.8 (2)
H15C—C15—H15B	109.5	C2—N1—C5	115.3 (2)
C14—C15—H15A	109.5	C9—N1—C5	117.79 (19)
H15C—C15—H15A	109.5	C16—N2—C23	126.4 (2)
H15B—C15—H15A	109.5	C16—N2—C19	115.5 (2)
O6—C16—N2	125.5 (3)	C23—N2—C19	118.0 (2)
O6—C16—C17	126.5 (3)	C10—O2—C6	118.56 (18)
N2—C16—C17	108.0 (2)	C12—O4—C7	117.92 (17)
C18—C17—C16	105.7 (2)	C24—O7—C20	119.2 (2)
C18—C17—H17B	110.6	C26—O9—C21	117.9 (2)
O1—C2—C3—C4	178.3 (3)	C28—C22—C23—N2	70.5 (3)
N1—C2—C3—C4	−2.4 (4)	C21—C22—C28—C29	−169.1 (3)
C2—C3—C4—C5	4.3 (4)	C23—C22—C28—C29	67.9 (3)
C3—C4—C5—N1	−4.5 (3)	O1—C2—N1—C9	1.4 (4)
C3—C4—C5—C6	−123.1 (3)	C3—C2—N1—C9	−178.0 (2)
N1—C5—C6—O2	168.45 (16)	O1—C2—N1—C5	178.7 (2)
C4—C5—C6—O2	−75.6 (2)	C3—C2—N1—C5	−0.7 (3)
N1—C5—C6—C7	51.2 (2)	C8—C9—N1—C2	−123.6 (3)
C4—C5—C6—C7	167.1 (2)	C8—C9—N1—C5	59.2 (3)
O2—C6—C7—O4	63.58 (19)	C6—C5—N1—C2	126.7 (2)
C5—C6—C7—O4	−178.43 (16)	C4—C5—N1—C2	3.3 (3)
O2—C6—C7—C8	−173.87 (15)	C6—C5—N1—C9	−55.8 (2)
C5—C6—C7—C8	−55.9 (2)	C4—C5—N1—C9	−179.1 (2)
O4—C7—C8—C14	49.6 (3)	O6—C16—N2—C23	−4.8 (4)
C6—C7—C8—C14	−69.1 (3)	C17—C16—N2—C23	175.7 (2)
O4—C7—C8—C9	175.27 (17)	O6—C16—N2—C19	178.6 (2)
C6—C7—C8—C9	56.6 (2)	C17—C16—N2—C19	−0.9 (3)
C14—C8—C9—N1	70.6 (3)	C22—C23—N2—C16	−119.1 (3)
C7—C8—C9—N1	−55.3 (2)	C22—C23—N2—C19	57.5 (3)
C7—C8—C14—C15	−169.6 (3)	C20—C19—N2—C16	122.6 (2)
C9—C8—C14—C15	67.9 (3)	C18—C19—N2—C16	−0.8 (3)
O6—C16—C17—C18	−177.2 (3)	C20—C19—N2—C23	−54.4 (3)
N2—C16—C17—C18	2.3 (3)	C18—C19—N2—C23	−177.7 (2)
C16—C17—C18—C19	−2.7 (4)	O3—C10—O2—C6	−9.7 (4)
C17—C18—C19—N2	2.2 (3)	C11—C10—O2—C6	171.5 (2)
C17—C18—C19—C20	−117.2 (3)	C7—C6—O2—C10	−122.9 (2)
N2—C19—C20—O7	168.15 (17)	C5—C6—O2—C10	117.4 (2)
C18—C19—C20—O7	−75.9 (3)	O5—C12—O4—C7	−4.5 (3)
N2—C19—C20—C21	50.9 (3)	C13—C12—O4—C7	175.3 (2)
C18—C19—C20—C21	166.8 (2)	C6—C7—O4—C12	−152.11 (19)
O7—C20—C21—O9	64.3 (2)	C8—C7—O4—C12	84.9 (2)
C19—C20—C21—O9	−178.50 (19)	O8—C24—O7—C20	−6.5 (5)
O7—C20—C21—C22	−173.53 (16)	C25—C24—O7—C20	173.8 (3)
C19—C20—C21—C22	−56.3 (2)	C19—C20—O7—C24	122.2 (2)
O9—C21—C22—C23	175.42 (17)	C21—C20—O7—C24	−118.5 (2)
C20—C21—C22—C23	57.7 (2)	O10—C26—O9—C21	−5.7 (4)
O9—C21—C22—C28	49.4 (3)	C27—C26—O9—C21	174.1 (2)
C20—C21—C22—C28	−68.3 (3)	C20—C21—O9—C26	−154.8 (2)
C21—C22—C23—N2	−55.4 (3)	C22—C21—O9—C26	83.3 (3)