8-{[(E)-3-(2-Chloro-phen-yl)acrylo-yloxy]imino}-12,13-ep-oxy-trichethec-9-en-4-yl (E)-3-(2-chloro-phen-yl)acrylate.

In the title compound, C(33)H(31)Cl(2)NO(6), the five-membered ring displays an envelope conformation, whereas the two six-membered rings both exhibit a chair conformation. As for the seven-membered ring, the dihedral angle between the mean planes formed by the four C atoms of the envelope unit and the three C and one O atoms of the six-membered chair is 69.08 (4)°, and these two mean planes are nearly perpendicular to the ep-oxy ring, making dihedral angles of 87.53 (4) and 88.67 (4)°, respectively.

Related literature

The endophytic fungi Trichoderma taxi sp. nov. from Taxus mairei S. Y. Hu can produce a compound with fungicidal activity, Trichodermin (Zhang et al., 2007 ▶), which is a member of the 4β-acet­oxy-12,13-ep­oxy­trichothecene family (Nielsen et al., 2005 ▶). For a related Trichodermin structure, see: Chen et al. (2008 ▶). For structures of Trichodermin derivatives, see: Cheng et al. (2009 ▶); Xu et al. (2010 ▶).

Experimental

Crystal data

C33H31Cl2NO6

M = 608.49

Monoclinic,

a = 7.2302 (4) Å

b = 14.4055 (6) Å

c = 14.6663 (6) Å

β = 94.414 (1)°

V = 1523.03 (12) Å3

Z = 2

Mo Kα radiation

μ = 0.26 mm−1

T = 296 K

0.41 × 0.36 × 0.29 mm

Data collection

Rigaku R-AXIS RAPID/ZJUG diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.895, T max = 0.929

15059 measured reflections

6713 independent reflections

3890 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.130

S = 1.00

6713 reflections

384 parameters

7 restraints

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.30 e Å−3

Absolute structure: Flack (1983 ▶), 3099 Friedel pairs

Flack parameter: 0.02 (8)

Data collection: PROCESS-AUTO (Rigaku, 2006 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku, 2007) ▶; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811039638/zq2124sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811039638/zq2124Isup2.hkl

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

C33H31Cl2NO6	F(000) = 636
Mr = 608.49	Dx = 1.327 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 9966 reflections
a = 7.2302 (4) Å	θ = 3.1–27.4°
b = 14.4055 (6) Å	µ = 0.26 mm−1
c = 14.6663 (6) Å	T = 296 K
β = 94.414 (1)°	Chunk, colourless
V = 1523.03 (12) Å3	0.41 × 0.36 × 0.29 mm
Z = 2

Rigaku R-AXIS RAPID/ZJUG diffractometer	6713 independent reflections
Radiation source: rolling anode	3890 reflections with I > 2σ(I)
graphite	Rint = 0.026
Detector resolution: 10.00 pixels mm-1	θmax = 27.4°, θmin = 3.1°
ω scans	h = −9→9
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −18→18
Tmin = 0.895, Tmax = 0.929	l = −18→18
15059 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.040	w = 1/[σ2(Fo2) + (0.0437P)2 + 0.8334P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.130	(Δ/σ)max < 0.001
S = 1.00	Δρmax = 0.40 e Å−3
6713 reflections	Δρmin = −0.30 e Å−3
384 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
7 restraints	Extinction coefficient: 0.0140 (15)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 3099 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.02 (8)

Experimental. ESI-MS: 631.5 (M+Na)+ (100%); 1H-NMR (500 MHz, CDCl3): 8.27–8.15 (2H, dd, J1 = J2 = 16.0 Hz, 2H-CH—Ar), 7.72–7.64 (2H, m, 2H-3-Ar), 7.47–7.43 (2H, m, 2H-6-Ar), 7.38–7.28 (4H, m, 4H-4,5-Ar), 6.66–6.48 (2H, dd, J1 = J2 = 16.0 Hz, 2H-COCH), 6.10–6.08 (1H, dd, J = 3.5, 7.5 Hz, H4), 5.69–5.67 (1H, d, J = 5.5 Hz, H-10), 3.65 (1H, d, J = 5.5 Hz, H11), 3.86 (1H, d, J = 7.5 Hz, H2), 3.22–3.21 (1H, d, J = 4.0 Hz, H13), 3.18–3.15 (1H, d, J = 15.5 Hz, H7), 2.99–2.98 (1H, d, J = 4.0 Hz, H13), 2.71–2.67 (1H, m, H-3), 2.66–2.63 (1H, d, J = 15.5 Hz, H7), 2.21–2.16 (1H, m, H-3), 2.08 (3H, s, H-16), 1.06 (3H, s, H-14), 0.89 (3H, s, H-15).

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
Cl1	−0.06472 (18)	0.61733 (11)	0.92949 (9)	0.0927 (4)
Cl2	0.1261 (2)	0.79377 (10)	0.29996 (11)	0.1019 (5)
O1	1.0020 (3)	0.56786 (16)	0.48929 (17)	0.0504 (6)
O2	0.7296 (4)	0.76494 (16)	0.56209 (17)	0.0543 (6)
O3	0.6673 (3)	0.63093 (17)	0.72185 (16)	0.0536 (6)
O4	0.4986 (5)	0.5146 (2)	0.7750 (3)	0.1002 (12)
O5	0.3826 (4)	0.4871 (2)	0.24887 (18)	0.0630 (7)
O6	0.3161 (6)	0.4193 (4)	0.1137 (3)	0.129 (2)
N1	0.5490 (4)	0.4323 (2)	0.2564 (2)	0.0595 (8)
C2	0.9633 (4)	0.6377 (2)	0.5546 (2)	0.0491 (8)
H2	1.0539	0.6883	0.5547	0.059*
C3	0.9472 (5)	0.6005 (3)	0.6506 (3)	0.0551 (9)
H3A	0.9799	0.6481	0.6958	0.066*
H3B	1.0285	0.5476	0.6623	0.066*
C4	0.7444 (5)	0.5718 (3)	0.6541 (2)	0.0496 (8)
H4	0.7331	0.5060	0.6696	0.060*
C5	0.6473 (4)	0.5939 (2)	0.5573 (2)	0.0424 (7)
C6	0.6787 (4)	0.5101 (2)	0.4915 (2)	0.0440 (8)
C7	0.6125 (5)	0.5343 (2)	0.3920 (2)	0.0507 (9)
H7A	0.4800	0.5462	0.3881	0.061*
H7B	0.6740	0.5905	0.3742	0.061*
C9	0.8307 (5)	0.4096 (2)	0.3412 (3)	0.0529 (9)
C8	0.6522 (5)	0.4579 (2)	0.3274 (3)	0.0499 (8)
C10	0.9381 (5)	0.4258 (3)	0.4174 (3)	0.0557 (9)
H10	1.0537	0.3973	0.4234	0.067*
C11	0.8862 (5)	0.4870 (2)	0.4945 (2)	0.0482 (8)
H11	0.9211	0.4551	0.5523	0.058*
C12	0.7696 (5)	0.6729 (2)	0.5303 (2)	0.0420 (7)
C13	0.7247 (6)	0.7472 (3)	0.4653 (3)	0.0580 (10)
H13A	0.8243	0.7723	0.4321	0.070*
H13B	0.6044	0.7455	0.4312	0.070*
C14	0.4438 (5)	0.6208 (3)	0.5593 (3)	0.0581 (9)
H14A	0.4343	0.6772	0.5934	0.087*
H14B	0.3783	0.5721	0.5879	0.087*
H14C	0.3908	0.6298	0.4979	0.087*
C15	0.5706 (6)	0.4250 (3)	0.5197 (3)	0.0618 (10)
H15A	0.6037	0.3724	0.4843	0.093*
H15B	0.4400	0.4367	0.5091	0.093*
H15C	0.6002	0.4126	0.5835	0.093*
C16	0.8876 (6)	0.3440 (3)	0.2685 (3)	0.0720 (12)
H16A	1.0136	0.3247	0.2828	0.108*
H16B	0.8776	0.3748	0.2103	0.108*
H16C	0.8079	0.2906	0.2661	0.108*
C17	0.5438 (6)	0.5955 (3)	0.7761 (3)	0.0633 (10)
C18	0.4717 (6)	0.6688 (3)	0.8326 (3)	0.0615 (10)
H18	0.5244	0.7276	0.8317	0.074*
C19	0.3334 (6)	0.6537 (3)	0.8852 (3)	0.0608 (10)
H19	0.2873	0.5935	0.8873	0.073*
C20	0.2477 (6)	0.7241 (3)	0.9399 (2)	0.0585 (10)
C21	0.3411 (7)	0.8050 (3)	0.9676 (3)	0.0729 (12)
H21	0.4628	0.8137	0.9530	0.087*
C22	0.2555 (9)	0.8728 (4)	1.0165 (3)	0.0877 (15)
H22	0.3199	0.9264	1.0346	0.105*
C23	0.0763 (10)	0.8608 (4)	1.0381 (4)	0.0973 (18)
H23	0.0196	0.9063	1.0714	0.117*
C24	−0.0192 (8)	0.7831 (4)	1.0113 (3)	0.0857 (15)
H24	−0.1418	0.7759	1.0251	0.103*
C25	0.0657 (6)	0.7153 (3)	0.9640 (3)	0.0656 (11)
C26	0.2778 (6)	0.4734 (4)	0.1713 (3)	0.0763 (14)
C27	0.1139 (6)	0.5335 (3)	0.1633 (3)	0.0686 (12)
H27	0.0286	0.5240	0.1134	0.082*
C28	0.0775 (5)	0.5998 (3)	0.2207 (3)	0.0583 (9)
H28	0.1621	0.6087	0.2710	0.070*
C29	−0.0846 (5)	0.6608 (3)	0.2125 (2)	0.0576 (10)
C30	−0.2520 (6)	0.6318 (4)	0.1689 (3)	0.0698 (11)
H30	−0.2623	0.5720	0.1454	0.084*
C31	−0.4065 (6)	0.6916 (4)	0.1599 (4)	0.0813 (14)
H31	−0.5183	0.6711	0.1314	0.098*
C32	−0.3908 (8)	0.7799 (4)	0.1935 (4)	0.0892 (16)
H32	−0.4923	0.8197	0.1870	0.107*
C33	−0.2279 (8)	0.8105 (4)	0.2363 (3)	0.0842 (14)
H33	−0.2183	0.8706	0.2591	0.101*
C34	−0.0785 (6)	0.7516 (3)	0.2454 (3)	0.0672 (11)

	U11	U22	U33	U12	U13	U23
Cl1	0.0732 (8)	0.1191 (11)	0.0855 (8)	−0.0194 (8)	0.0046 (6)	0.0097 (8)
Cl2	0.0834 (9)	0.1012 (10)	0.1193 (11)	−0.0005 (7)	−0.0035 (7)	−0.0454 (9)
O1	0.0376 (13)	0.0466 (13)	0.0668 (15)	−0.0018 (10)	0.0037 (10)	−0.0122 (12)
O2	0.0618 (16)	0.0385 (12)	0.0630 (15)	0.0037 (11)	0.0075 (12)	−0.0072 (11)
O3	0.0580 (15)	0.0511 (14)	0.0526 (13)	−0.0015 (12)	0.0095 (11)	−0.0035 (12)
O4	0.128 (3)	0.059 (2)	0.122 (3)	−0.014 (2)	0.064 (2)	0.0020 (19)
O5	0.0541 (16)	0.0694 (17)	0.0616 (15)	0.0174 (14)	−0.0214 (12)	−0.0176 (13)
O6	0.114 (3)	0.152 (3)	0.114 (3)	0.059 (2)	−0.038 (2)	−0.073 (2)
N1	0.0535 (19)	0.0534 (17)	0.068 (2)	0.0142 (15)	−0.0163 (15)	−0.0115 (16)
C2	0.0325 (17)	0.0462 (18)	0.069 (2)	−0.0056 (15)	0.0032 (15)	−0.0147 (17)
C3	0.042 (2)	0.060 (2)	0.061 (2)	0.0008 (17)	−0.0074 (16)	−0.0075 (19)
C4	0.053 (2)	0.0473 (19)	0.0482 (19)	0.0009 (16)	−0.0013 (16)	−0.0035 (16)
C5	0.0335 (16)	0.0460 (18)	0.0472 (17)	−0.0020 (14)	0.0000 (13)	−0.0008 (14)
C6	0.0365 (18)	0.0396 (17)	0.0544 (19)	−0.0002 (14)	−0.0064 (14)	0.0004 (15)
C7	0.046 (2)	0.0465 (19)	0.058 (2)	0.0080 (15)	−0.0101 (16)	−0.0104 (17)
C9	0.052 (2)	0.0402 (18)	0.065 (2)	0.0086 (16)	−0.0057 (17)	−0.0101 (17)
C8	0.049 (2)	0.0427 (18)	0.056 (2)	0.0040 (15)	−0.0092 (16)	−0.0032 (16)
C10	0.049 (2)	0.0450 (19)	0.070 (2)	0.0134 (17)	−0.0114 (18)	−0.0118 (19)
C11	0.0438 (19)	0.0410 (18)	0.058 (2)	0.0047 (15)	−0.0089 (15)	−0.0017 (16)
C12	0.0410 (19)	0.0313 (15)	0.0537 (19)	0.0006 (13)	0.0028 (14)	−0.0070 (15)
C13	0.069 (3)	0.049 (2)	0.056 (2)	0.0059 (18)	0.0074 (18)	0.0017 (18)
C14	0.0392 (19)	0.069 (2)	0.066 (2)	0.0027 (19)	0.0039 (16)	−0.007 (2)
C15	0.061 (2)	0.050 (2)	0.073 (3)	−0.0163 (19)	−0.0029 (19)	0.004 (2)
C16	0.076 (3)	0.058 (2)	0.079 (3)	0.020 (2)	−0.010 (2)	−0.019 (2)
C17	0.071 (3)	0.060 (2)	0.060 (2)	−0.005 (2)	0.016 (2)	0.006 (2)
C18	0.066 (3)	0.063 (2)	0.056 (2)	0.002 (2)	0.0101 (19)	−0.001 (2)
C19	0.061 (2)	0.064 (2)	0.059 (2)	−0.001 (2)	0.0131 (18)	0.0076 (19)
C20	0.063 (3)	0.068 (2)	0.045 (2)	0.005 (2)	0.0067 (18)	0.0137 (19)
C21	0.080 (3)	0.072 (3)	0.068 (3)	−0.002 (3)	0.012 (2)	0.010 (2)
C22	0.118 (5)	0.069 (3)	0.078 (3)	0.003 (3)	0.021 (3)	0.003 (3)
C23	0.131 (5)	0.081 (4)	0.085 (4)	0.019 (4)	0.046 (3)	0.012 (3)
C24	0.083 (3)	0.098 (4)	0.080 (3)	0.023 (3)	0.031 (3)	0.018 (3)
C25	0.066 (3)	0.078 (3)	0.053 (2)	0.006 (2)	0.008 (2)	0.016 (2)
C26	0.063 (3)	0.094 (3)	0.068 (3)	0.027 (2)	−0.021 (2)	−0.031 (3)
C27	0.055 (2)	0.086 (3)	0.061 (2)	0.016 (2)	−0.0186 (19)	−0.016 (2)
C28	0.047 (2)	0.072 (3)	0.054 (2)	0.0062 (19)	−0.0057 (16)	−0.0058 (19)
C29	0.051 (2)	0.072 (3)	0.0490 (19)	0.0049 (19)	0.0008 (16)	0.0027 (19)
C30	0.057 (2)	0.083 (3)	0.068 (2)	0.001 (2)	−0.0038 (19)	0.016 (2)
C31	0.052 (3)	0.105 (4)	0.086 (3)	0.010 (3)	0.000 (2)	0.030 (3)
C32	0.074 (4)	0.107 (5)	0.088 (3)	0.029 (3)	0.019 (3)	0.023 (3)
C33	0.083 (4)	0.094 (4)	0.077 (3)	0.029 (3)	0.017 (3)	0.001 (3)
C34	0.068 (3)	0.076 (3)	0.058 (2)	0.013 (2)	0.007 (2)	−0.005 (2)

Cl1—C25	1.750 (5)	C14—H14A	0.9600
Cl2—C34	1.736 (5)	C14—H14B	0.9600
O1—C2	1.432 (4)	C14—H14C	0.9600
O1—C11	1.441 (4)	C15—H15A	0.9600
O2—C13	1.440 (4)	C15—H15B	0.9600
O2—C12	1.442 (4)	C15—H15C	0.9600
O3—C17	1.342 (5)	C16—H16A	0.9600
O3—C4	1.451 (4)	C16—H16B	0.9600
O4—C17	1.210 (5)	C16—H16C	0.9600
O5—C26	1.332 (4)	C17—C18	1.463 (6)
O5—N1	1.437 (4)	C18—C19	1.327 (5)
O6—C26	1.197 (5)	C18—H18	0.9300
N1—C8	1.286 (4)	C19—C20	1.461 (6)
C2—C12	1.506 (5)	C19—H19	0.9300
C2—C3	1.520 (5)	C20—C21	1.392 (6)
C2—H2	0.9800	C20—C25	1.394 (6)
C3—C4	1.528 (5)	C21—C22	1.385 (7)
C3—H3A	0.9700	C21—H21	0.9300
C3—H3B	0.9700	C22—C23	1.368 (8)
C4—C5	1.568 (5)	C22—H22	0.9300
C4—H4	0.9800	C23—C24	1.358 (8)
C5—C12	1.512 (4)	C23—H23	0.9300
C5—C14	1.523 (5)	C24—C25	1.371 (6)
C5—C6	1.574 (5)	C24—H24	0.9300
C6—C15	1.527 (5)	C26—C27	1.465 (6)
C6—C11	1.534 (5)	C27—C28	1.313 (5)
C6—C7	1.540 (5)	C27—H27	0.9300
C7—C8	1.495 (5)	C28—C29	1.462 (5)
C7—H7A	0.9700	C28—H28	0.9300
C7—H7B	0.9700	C29—C30	1.389 (6)
C9—C10	1.332 (5)	C29—C34	1.394 (6)
C9—C8	1.467 (5)	C30—C31	1.408 (6)
C9—C16	1.505 (5)	C30—H30	0.9300
C10—C11	1.503 (5)	C31—C32	1.365 (8)
C10—H10	0.9300	C31—H31	0.9300
C11—H11	0.9800	C32—C33	1.364 (8)
C12—C13	1.453 (5)	C32—H32	0.9300
C13—H13A	0.9700	C33—C34	1.371 (6)
C13—H13B	0.9700	C33—H33	0.9300
C2—O1—C11	112.9 (3)	H14A—C14—H14B	109.5
C13—O2—C12	60.6 (2)	C5—C14—H14C	109.5
C17—O3—C4	119.4 (3)	H14A—C14—H14C	109.5
C26—O5—N1	113.7 (3)	H14B—C14—H14C	109.5
C8—N1—O5	109.5 (3)	C6—C15—H15A	109.5
O1—C2—C12	107.7 (3)	C6—C15—H15B	109.5
O1—C2—C3	113.9 (3)	H15A—C15—H15B	109.5
C12—C2—C3	101.6 (3)	C6—C15—H15C	109.5
O1—C2—H2	111.1	H15A—C15—H15C	109.5
C12—C2—H2	111.1	H15B—C15—H15C	109.5
C3—C2—H2	111.1	C9—C16—H16A	109.5
C2—C3—C4	105.6 (3)	C9—C16—H16B	109.5
C2—C3—H3A	110.6	H16A—C16—H16B	109.5
C4—C3—H3A	110.6	C9—C16—H16C	109.5
C2—C3—H3B	110.6	H16A—C16—H16C	109.5
C4—C3—H3B	110.6	H16B—C16—H16C	109.5
H3A—C3—H3B	108.8	O4—C17—O3	123.4 (4)
O3—C4—C3	106.5 (3)	O4—C17—C18	126.5 (4)
O3—C4—C5	109.4 (3)	O3—C17—C18	110.1 (3)
C3—C4—C5	106.2 (3)	C19—C18—C17	121.9 (4)
O3—C4—H4	111.5	C19—C18—H18	119.1
C3—C4—H4	111.5	C17—C18—H18	119.1
C5—C4—H4	111.5	C18—C19—C20	125.2 (4)
C12—C5—C14	113.5 (3)	C18—C19—H19	117.4
C12—C5—C4	99.2 (3)	C20—C19—H19	117.4
C14—C5—C4	113.6 (3)	C21—C20—C25	116.6 (4)
C12—C5—C6	107.5 (2)	C21—C20—C19	121.7 (4)
C14—C5—C6	113.1 (3)	C25—C20—C19	121.6 (4)
C4—C5—C6	108.9 (3)	C22—C21—C20	121.0 (5)
C15—C6—C11	109.7 (3)	C22—C21—H21	119.5
C15—C6—C7	108.1 (3)	C20—C21—H21	119.5
C11—C6—C7	108.0 (3)	C23—C22—C21	120.0 (5)
C15—C6—C5	110.4 (3)	C23—C22—H22	120.0
C11—C6—C5	109.7 (3)	C21—C22—H22	120.0
C7—C6—C5	111.0 (3)	C24—C23—C22	120.4 (5)
C8—C7—C6	111.9 (3)	C24—C23—H23	119.8
C8—C7—H7A	109.2	C22—C23—H23	119.8
C6—C7—H7A	109.2	C23—C24—C25	119.8 (5)
C8—C7—H7B	109.2	C23—C24—H24	120.1
C6—C7—H7B	109.2	C25—C24—H24	120.1
H7A—C7—H7B	107.9	C24—C25—C20	122.1 (5)
C10—C9—C8	118.9 (3)	C24—C25—Cl1	117.9 (4)
C10—C9—C16	122.1 (3)	C20—C25—Cl1	119.9 (4)
C8—C9—C16	119.0 (3)	O6—C26—O5	123.5 (4)
N1—C8—C9	115.2 (3)	O6—C26—C27	123.9 (4)
N1—C8—C7	126.6 (3)	O5—C26—C27	112.6 (4)
C9—C8—C7	118.1 (3)	C28—C27—C26	125.4 (4)
C9—C10—C11	124.8 (3)	C28—C27—H27	117.3
C9—C10—H10	117.6	C26—C27—H27	117.3
C11—C10—H10	117.6	C27—C28—C29	125.7 (4)
O1—C11—C10	104.7 (3)	C27—C28—H28	117.2
O1—C11—C6	113.2 (3)	C29—C28—H28	117.2
C10—C11—C6	114.0 (3)	C30—C29—C34	116.4 (4)
O1—C11—H11	108.2	C30—C29—C28	121.5 (4)
C10—C11—H11	108.2	C34—C29—C28	122.1 (4)
C6—C11—H11	108.2	C29—C30—C31	121.1 (5)
O2—C12—C13	59.6 (2)	C29—C30—H30	119.5
O2—C12—C2	116.0 (3)	C31—C30—H30	119.5
C13—C12—C2	124.0 (3)	C32—C31—C30	119.5 (5)
O2—C12—C5	118.1 (3)	C32—C31—H31	120.2
C13—C12—C5	128.3 (3)	C30—C31—H31	120.2
C2—C12—C5	103.7 (3)	C33—C32—C31	120.7 (5)
O2—C13—C12	59.8 (2)	C33—C32—H32	119.6
O2—C13—H13A	117.8	C31—C32—H32	119.6
C12—C13—H13A	117.8	C32—C33—C34	119.4 (5)
O2—C13—H13B	117.8	C32—C33—H33	120.3
C12—C13—H13B	117.8	C34—C33—H33	120.3
H13A—C13—H13B	114.9	C33—C34—C29	122.8 (5)
C5—C14—H14A	109.5	C33—C34—Cl2	117.8 (4)
C5—C14—H14B	109.5	C29—C34—Cl2	119.4 (3)
C26—O5—N1—C8	172.1 (4)	O1—C2—C12—C13	−86.7 (4)
C11—O1—C2—C12	−65.2 (3)	C3—C2—C12—C13	153.4 (3)
C11—O1—C2—C3	46.7 (4)	O1—C2—C12—C5	72.6 (3)
O1—C2—C3—C4	−87.5 (3)	C3—C2—C12—C5	−47.4 (3)
C12—C2—C3—C4	28.0 (3)	C14—C5—C12—O2	37.1 (4)
C17—O3—C4—C3	−143.0 (3)	C4—C5—C12—O2	−83.8 (3)
C17—O3—C4—C5	102.6 (4)	C6—C5—C12—O2	162.9 (3)
C2—C3—C4—O3	−116.5 (3)	C14—C5—C12—C13	−34.9 (5)
C2—C3—C4—C5	0.1 (4)	C4—C5—C12—C13	−155.8 (3)
O3—C4—C5—C12	86.8 (3)	C6—C5—C12—C13	90.9 (4)
C3—C4—C5—C12	−27.8 (3)	C14—C5—C12—C2	167.0 (3)
O3—C4—C5—C14	−34.0 (4)	C4—C5—C12—C2	46.2 (3)
C3—C4—C5—C14	−148.6 (3)	C6—C5—C12—C2	−67.1 (3)
O3—C4—C5—C6	−161.0 (3)	C2—C12—C13—O2	−102.6 (3)
C3—C4—C5—C6	84.4 (3)	C5—C12—C13—O2	103.4 (4)
C12—C5—C6—C15	175.6 (3)	C4—O3—C17—O4	3.8 (6)
C14—C5—C6—C15	−58.3 (4)	C4—O3—C17—C18	−174.6 (3)
C4—C5—C6—C15	69.0 (3)	O4—C17—C18—C19	−5.6 (7)
C12—C5—C6—C11	54.6 (3)	O3—C17—C18—C19	172.8 (4)
C14—C5—C6—C11	−179.3 (3)	C17—C18—C19—C20	−176.8 (4)
C4—C5—C6—C11	−52.0 (3)	C18—C19—C20—C21	−22.9 (6)
C12—C5—C6—C7	−64.7 (3)	C18—C19—C20—C25	154.5 (4)
C14—C5—C6—C7	61.5 (4)	C25—C20—C21—C22	0.0 (6)
C4—C5—C6—C7	−171.2 (3)	C19—C20—C21—C22	177.5 (4)
C15—C6—C7—C8	−62.5 (4)	C20—C21—C22—C23	−0.2 (7)
C11—C6—C7—C8	56.1 (4)	C21—C22—C23—C24	−0.5 (8)
C5—C6—C7—C8	176.3 (3)	C22—C23—C24—C25	1.4 (8)
O5—N1—C8—C9	−177.8 (3)	C23—C24—C25—C20	−1.6 (7)
O5—N1—C8—C7	−1.6 (5)	C23—C24—C25—Cl1	−179.0 (4)
C10—C9—C8—N1	−173.9 (4)	C21—C20—C25—C24	0.9 (6)
C16—C9—C8—N1	6.7 (6)	C19—C20—C25—C24	−176.6 (4)
C10—C9—C8—C7	9.6 (6)	C21—C20—C25—Cl1	178.3 (3)
C16—C9—C8—C7	−169.8 (4)	C19—C20—C25—Cl1	0.8 (5)
C6—C7—C8—N1	143.3 (4)	N1—O5—C26—O6	1.4 (7)
C6—C7—C8—C9	−40.6 (5)	N1—O5—C26—C27	−177.1 (4)
C8—C9—C10—C11	3.5 (6)	O6—C26—C27—C28	−172.9 (6)
C16—C9—C10—C11	−177.1 (4)	O5—C26—C27—C28	5.6 (7)
C2—O1—C11—C10	176.1 (3)	C26—C27—C28—C29	179.2 (4)
C2—O1—C11—C6	51.4 (4)	C27—C28—C29—C30	28.8 (6)
C9—C10—C11—O1	−108.8 (4)	C27—C28—C29—C34	−149.4 (4)
C9—C10—C11—C6	15.4 (5)	C34—C29—C30—C31	−0.6 (6)
C15—C6—C11—O1	−166.7 (3)	C28—C29—C30—C31	−178.9 (4)
C7—C6—C11—O1	75.8 (3)	C29—C30—C31—C32	0.9 (7)
C5—C6—C11—O1	−45.3 (4)	C30—C31—C32—C33	−0.6 (7)
C15—C6—C11—C10	73.8 (4)	C31—C32—C33—C34	0.1 (8)
C7—C6—C11—C10	−43.8 (4)	C32—C33—C34—C29	0.2 (7)
C5—C6—C11—C10	−164.8 (3)	C32—C33—C34—Cl2	179.7 (4)
C13—O2—C12—C2	115.8 (4)	C30—C29—C34—C33	0.1 (6)
C13—O2—C12—C5	−120.1 (4)	C28—C29—C34—C33	178.4 (4)
O1—C2—C12—O2	−156.3 (3)	C30—C29—C34—Cl2	−179.5 (3)
C3—C2—C12—O2	83.8 (3)	C28—C29—C34—Cl2	−1.2 (6)