9-[(Furan-2-ylmeth-yl)amino]-5-(3,4,5-trimeth-oxy-phen-yl)-5,5a,8a,9-tetra-hydro-furo[3',4':6,7]naphtho-[2,3-d][1,3]dioxol-6(8H)-one.

In title compound, C(27)H(27)NO(8), the dihydrofuran-2(3H)-one ring and the six-membered ring fused to it both display envelope conformations. The dihedral angle between the benzene ring of the benzo[d][1,3]dioxole group and the other benzene ring is 60.59 (2)°. In the crystal, weak inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into a three-dimensional network. The furan ring is disordered over two sets of sites with occupancies of 0.722 (7) and 0.278 (7).

Related literature

For podophyllotoxin derivatives synthesized by our group, see: Lu et al. (2010 ▶); Yu et al. (2008 ▶); Zhao et al. (2009 ▶). For bond-length and angle data of related structures, see: Feng et al. (2008 ▶); Zhang et al. (1994 ▶); Zuo et al. (2009 ▶).

Experimental

Crystal data

C27H27NO8

M = 493.50

Monoclinic,

a = 11.7374 (15) Å

b = 8.4087 (8) Å

c = 11.8848 (16) Å

β = 102.693 (5)°

V = 1144.3 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 113 K

0.20 × 0.18 × 0.12 mm

Data collection

Rigaku Saturn724 CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2007 ▶) T min = 0.979, T max = 0.987

14991 measured reflections

2950 independent reflections

2262 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.067

S = 0.97

2950 reflections

372 parameters

41 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CrystalClear (Rigaku, 2007 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811027735/rz2621sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811027735/rz2621Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811027735/rz2621Isup3.cml

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

C27H27NO8	F(000) = 520
Mr = 493.50	Dx = 1.432 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 4290 reflections
a = 11.7374 (15) Å	θ = 1.8–28.0°
b = 8.4087 (8) Å	µ = 0.11 mm−1
c = 11.8848 (16) Å	T = 113 K
β = 102.693 (5)°	Prism, colourless
V = 1144.3 (2) Å3	0.20 × 0.18 × 0.12 mm
Z = 2

Rigaku Saturn724 CCD diffractometer	2950 independent reflections
Radiation source: rotating anode	2262 reflections with I > 2σ(I)
multilayer	Rint = 0.047
Detector resolution: 14.22 pixels mm-1	θmax = 28.0°, θmin = 1.8°
ω and φ scans	h = −15→15
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007)	k = −11→10
Tmin = 0.979, Tmax = 0.987	l = −15→15
14991 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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.067	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	w = 1/[σ2(Fo2) + (0.036P)2] where P = (Fo2 + 2Fc2)/3
2950 reflections	(Δ/σ)max = 0.001
372 parameters	Δρmax = 0.17 e Å−3
41 restraints	Δρmin = −0.22 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)
O1	1.3701 (3)	0.9258 (3)	0.7345 (3)	0.0259 (8)	0.722 (7)
C1	1.4119 (3)	0.9416 (4)	0.6362 (3)	0.0258 (9)	0.722 (7)
H1A	1.4695	1.0165	0.6263	0.031*	0.722 (7)
C2	1.3609 (4)	0.8374 (6)	0.5562 (4)	0.0255 (13)	0.722 (7)
H2	1.3750	0.8249	0.4810	0.031*	0.722 (7)
C3	1.2805 (3)	0.7482 (5)	0.6062 (3)	0.0225 (8)	0.722 (7)
H3	1.2312	0.6647	0.5703	0.027*	0.722 (7)
C4	1.2879 (4)	0.8046 (6)	0.7136 (4)	0.0219 (5)	0.722 (7)
O1'	1.2713 (6)	0.6797 (10)	0.6369 (6)	0.029 (2)	0.278 (7)
C1'	1.3229 (8)	0.7386 (14)	0.5538 (7)	0.032 (3)	0.278 (7)
H1'	1.3261	0.6824	0.4852	0.038*	0.278 (7)
C2'	1.3680 (11)	0.8821 (13)	0.5781 (10)	0.034 (5)	0.278 (7)
H2'	1.4078	0.9450	0.5325	0.040*	0.278 (7)
C3'	1.3437 (11)	0.9230 (11)	0.6900 (10)	0.027 (3)	0.278 (7)
H3'	1.3639	1.0178	0.7332	0.033*	0.278 (7)
C4'	1.2882 (10)	0.8003 (14)	0.7168 (9)	0.0219 (5)	0.278 (7)
O2	0.86595 (12)	0.7908 (2)	0.34547 (11)	0.0321 (4)
O3	0.67662 (11)	0.79787 (18)	0.36877 (11)	0.0236 (3)
O4	1.00549 (13)	0.9413 (2)	1.06166 (11)	0.0362 (4)
O5	0.81900 (13)	0.8872 (2)	1.05584 (13)	0.0388 (4)
O6	0.52676 (11)	1.28410 (17)	0.92051 (12)	0.0234 (3)
O7	0.62669 (11)	1.52498 (15)	0.83580 (11)	0.0185 (3)
O8	0.79077 (11)	1.47895 (16)	0.71823 (11)	0.0174 (3)
N1	1.10768 (16)	0.7428 (2)	0.77354 (18)	0.0272 (4)
C5	1.23354 (16)	0.7632 (3)	0.81295 (17)	0.0244 (5)
H5A	1.2492	0.8466	0.8694	0.029*	0.722 (7)
H5B	1.2673	0.6666	0.8485	0.029*	0.722 (7)
H5C	1.2489	0.8474	0.8688	0.029*	0.278 (7)
H5D	1.2669	0.6670	0.8495	0.029*	0.278 (7)
C6	1.04161 (16)	0.8907 (2)	0.75745 (16)	0.0186 (4)
H6	1.0923	0.9741	0.7336	0.022*
C7	0.93416 (15)	0.8704 (2)	0.65914 (16)	0.0164 (4)
C8	0.95707 (17)	0.8448 (3)	0.54918 (16)	0.0216 (4)
H8	1.0349	0.8434	0.5385	0.026*
C9	0.86540 (16)	0.8223 (2)	0.45889 (16)	0.0211 (4)
C10	0.74725 (18)	0.8030 (3)	0.28551 (17)	0.0291 (5)
H10A	0.7269	0.7138	0.2304	0.035*
H10B	0.7343	0.9040	0.2419	0.035*
C11	0.75225 (16)	0.8251 (2)	0.47291 (16)	0.0182 (4)
C12	0.72683 (16)	0.8476 (2)	0.57774 (16)	0.0168 (4)
H12	0.6483	0.8477	0.5863	0.020*
C13	0.81992 (16)	0.8708 (2)	0.67332 (16)	0.0159 (4)
C14	0.78895 (16)	0.8993 (2)	0.78943 (16)	0.0164 (4)
H14	0.7264	0.8221	0.7974	0.020*
C15	0.89755 (16)	0.8617 (2)	0.88232 (16)	0.0191 (4)
H15	0.9140	0.7457	0.8766	0.023*
C16	0.89706 (19)	0.8959 (3)	1.00600 (18)	0.0283 (5)
C17	1.08442 (18)	0.9333 (3)	0.98287 (17)	0.0280 (5)
H17A	1.1261	0.8302	0.9899	0.034*
H17B	1.1424	1.0205	0.9980	0.034*
C18	1.00434 (16)	0.9508 (3)	0.86503 (16)	0.0200 (4)
H18	0.9831	1.0657	0.8531	0.024*
C19	0.74248 (16)	1.0657 (2)	0.79825 (15)	0.0147 (4)
C20	0.78823 (15)	1.1934 (2)	0.74867 (16)	0.0151 (4)
H20	0.8466	1.1755	0.7060	0.018*
C21	0.74977 (15)	1.3459 (2)	0.76073 (15)	0.0148 (4)
C22	0.66214 (15)	1.3726 (2)	0.81994 (16)	0.0151 (4)
C23	0.61405 (15)	1.2451 (2)	0.86715 (16)	0.0166 (4)
C24	0.65474 (16)	1.0917 (2)	0.85763 (16)	0.0164 (4)
H24	0.6227	1.0050	0.8916	0.020*
C25	0.88269 (16)	1.4550 (2)	0.65900 (16)	0.0182 (4)
H25A	0.9504	1.4086	0.7120	0.027*
H25B	0.9048	1.5573	0.6304	0.027*
H25C	0.8561	1.3827	0.5938	0.027*
C26	0.54369 (17)	1.5820 (3)	0.73793 (18)	0.0254 (5)
H26A	0.5794	1.5843	0.6708	0.038*
H26B	0.5190	1.6896	0.7536	0.038*
H26C	0.4757	1.5113	0.7222	0.038*
C27	0.47759 (17)	1.1602 (3)	0.97667 (17)	0.0227 (5)
H27A	0.4453	1.0777	0.9204	0.034*
H27B	0.4153	1.2039	1.0104	0.034*
H27C	0.5384	1.1139	1.0378	0.034*
H1	1.086 (2)	0.676 (4)	0.803 (2)	0.056 (10)*

	U11	U22	U33	U12	U13	U23
O1	0.0233 (16)	0.0261 (14)	0.0294 (18)	0.0016 (11)	0.0081 (13)	−0.0019 (12)
C1	0.0237 (17)	0.0275 (18)	0.0266 (19)	0.0037 (14)	0.0063 (15)	0.0045 (16)
C2	0.021 (2)	0.031 (3)	0.023 (2)	0.003 (2)	0.0028 (15)	0.004 (2)
C3	0.0174 (17)	0.029 (2)	0.020 (2)	0.0030 (17)	0.0016 (14)	0.0017 (17)
C4	0.0147 (9)	0.0226 (12)	0.0261 (11)	0.0049 (9)	−0.0004 (8)	−0.0031 (9)
O1'	0.027 (3)	0.037 (5)	0.022 (4)	0.004 (3)	0.002 (3)	−0.005 (3)
C1'	0.030 (5)	0.040 (6)	0.024 (4)	0.010 (5)	0.002 (4)	0.009 (4)
C2'	0.037 (7)	0.044 (8)	0.022 (6)	0.004 (5)	0.010 (5)	0.008 (6)
C3'	0.031 (5)	0.019 (5)	0.031 (6)	0.009 (4)	0.007 (5)	0.003 (4)
C4'	0.0147 (9)	0.0226 (12)	0.0261 (11)	0.0049 (9)	−0.0004 (8)	−0.0031 (9)
O2	0.0278 (8)	0.0550 (11)	0.0151 (7)	−0.0014 (8)	0.0079 (6)	−0.0012 (7)
O3	0.0236 (7)	0.0315 (9)	0.0156 (7)	−0.0025 (7)	0.0038 (6)	−0.0010 (6)
O4	0.0300 (8)	0.0597 (12)	0.0172 (7)	0.0130 (8)	0.0012 (7)	−0.0025 (8)
O5	0.0378 (9)	0.0615 (12)	0.0202 (8)	0.0147 (8)	0.0132 (7)	0.0081 (8)
O6	0.0262 (7)	0.0208 (8)	0.0295 (8)	0.0029 (6)	0.0195 (6)	0.0037 (6)
O7	0.0215 (7)	0.0163 (7)	0.0186 (7)	0.0047 (6)	0.0065 (6)	0.0007 (6)
O8	0.0189 (7)	0.0149 (7)	0.0210 (7)	0.0012 (5)	0.0102 (6)	0.0022 (6)
N1	0.0166 (9)	0.0188 (10)	0.0440 (12)	0.0032 (8)	0.0019 (8)	0.0030 (9)
C5	0.0178 (10)	0.0288 (13)	0.0250 (11)	0.0052 (9)	0.0011 (8)	−0.0034 (9)
C6	0.0180 (9)	0.0163 (10)	0.0228 (10)	0.0021 (8)	0.0069 (8)	0.0021 (8)
C7	0.0190 (9)	0.0124 (9)	0.0187 (10)	0.0009 (8)	0.0062 (8)	0.0028 (8)
C8	0.0188 (9)	0.0261 (12)	0.0223 (10)	0.0008 (9)	0.0095 (8)	0.0043 (9)
C9	0.0269 (11)	0.0237 (11)	0.0154 (10)	0.0002 (9)	0.0107 (8)	0.0026 (9)
C10	0.0290 (11)	0.0415 (14)	0.0175 (10)	0.0022 (11)	0.0067 (9)	−0.0018 (10)
C11	0.0208 (10)	0.0160 (10)	0.0174 (9)	−0.0011 (8)	0.0031 (8)	0.0010 (8)
C12	0.0170 (9)	0.0144 (10)	0.0198 (10)	−0.0001 (8)	0.0062 (8)	0.0006 (8)
C13	0.0211 (9)	0.0107 (9)	0.0171 (9)	0.0019 (8)	0.0070 (8)	0.0019 (8)
C14	0.0181 (9)	0.0157 (10)	0.0170 (9)	0.0003 (8)	0.0070 (7)	0.0009 (8)
C15	0.0233 (10)	0.0188 (10)	0.0157 (9)	0.0058 (9)	0.0058 (8)	0.0035 (8)
C16	0.0304 (11)	0.0353 (13)	0.0189 (10)	0.0121 (11)	0.0050 (9)	0.0056 (10)
C17	0.0235 (11)	0.0377 (13)	0.0217 (10)	0.0083 (10)	0.0027 (9)	−0.0007 (10)
C18	0.0201 (10)	0.0217 (11)	0.0173 (9)	0.0040 (9)	0.0016 (8)	0.0019 (9)
C19	0.0152 (9)	0.0163 (10)	0.0122 (9)	0.0011 (8)	0.0020 (7)	−0.0005 (8)
C20	0.0132 (8)	0.0187 (10)	0.0139 (9)	0.0017 (8)	0.0042 (7)	0.0000 (7)
C21	0.0143 (8)	0.0178 (10)	0.0119 (9)	−0.0009 (8)	0.0017 (7)	0.0029 (8)
C22	0.0167 (9)	0.0144 (9)	0.0145 (9)	0.0035 (8)	0.0039 (7)	−0.0002 (8)
C23	0.0161 (9)	0.0207 (11)	0.0150 (9)	0.0015 (8)	0.0073 (7)	0.0005 (8)
C24	0.0179 (10)	0.0165 (10)	0.0155 (9)	−0.0018 (8)	0.0054 (8)	0.0016 (8)
C25	0.0186 (9)	0.0177 (10)	0.0212 (10)	−0.0037 (8)	0.0103 (8)	0.0001 (9)
C26	0.0224 (11)	0.0200 (11)	0.0323 (12)	0.0059 (9)	0.0030 (9)	0.0037 (9)
C27	0.0225 (11)	0.0262 (12)	0.0232 (11)	−0.0024 (9)	0.0129 (9)	0.0033 (9)

O1—C1	1.370 (4)	C6—H6	1.0000
O1—C4	1.388 (5)	C7—C13	1.388 (2)
C1—C2	1.334 (5)	C7—C8	1.407 (2)
C1—H1A	0.9500	C8—C9	1.356 (3)
C2—C3	1.432 (6)	C8—H8	0.9500
C2—H2	0.9500	C9—C11	1.375 (2)
C3—C4	1.346 (5)	C10—H10A	0.9900
C3—H3	0.9500	C10—H10B	0.9900
C4—C5	1.502 (4)	C11—C12	1.357 (3)
O1'—C1'	1.360 (8)	C12—C13	1.406 (2)
O1'—C4'	1.374 (9)	C12—H12	0.9500
C1'—C2'	1.324 (9)	C13—C14	1.521 (2)
C1'—H1'	0.9500	C14—C19	1.514 (3)
C2'—C3'	1.461 (9)	C14—C15	1.525 (3)
C2'—H2'	0.9500	C14—H14	1.0000
C3'—C4'	1.297 (9)	C15—C16	1.499 (3)
C3'—H3'	0.9500	C15—C18	1.512 (3)
C4'—C5	1.461 (9)	C15—H15	1.0000
O2—C9	1.375 (2)	C17—C18	1.513 (3)
O2—C10	1.422 (2)	C17—H17A	0.9900
O3—C11	1.374 (2)	C17—H17B	0.9900
O3—C10	1.424 (2)	C18—H18	1.0000
O4—C16	1.354 (3)	C19—C24	1.388 (3)
O4—C17	1.456 (2)	C19—C20	1.389 (3)
O5—C16	1.198 (2)	C20—C21	1.377 (3)
O6—C23	1.358 (2)	C20—H20	0.9500
O6—C27	1.426 (2)	C21—C22	1.386 (2)
O7—C22	1.373 (2)	C22—C23	1.387 (3)
O7—C26	1.426 (2)	C23—C24	1.389 (3)
O8—C21	1.358 (2)	C24—H24	0.9500
O8—C25	1.426 (2)	C25—H25A	0.9800
N1—C6	1.456 (3)	C25—H25B	0.9800
N1—C5	1.458 (2)	C25—H25C	0.9800
N1—H1	0.74 (3)	C26—H26A	0.9800
C5—H5A	0.9601	C26—H26B	0.9800
C5—H5B	0.9600	C26—H26C	0.9800
C5—H5C	0.9600	C27—H27A	0.9800
C5—H5D	0.9600	C27—H27B	0.9800
C6—C18	1.525 (3)	C27—H27C	0.9800
C6—C7	1.529 (3)
C1—O1—C4	106.4 (3)	H10A—C10—H10B	108.5
C2—C1—O1	110.8 (3)	C12—C11—O3	128.41 (17)
C2—C1—H1A	124.6	C12—C11—C9	121.80 (18)
O1—C1—H1A	124.6	O3—C11—C9	109.76 (16)
C1—C2—C3	106.4 (4)	C11—C12—C13	118.20 (17)
C1—C2—H2	126.8	C11—C12—H12	120.9
C3—C2—H2	126.8	C13—C12—H12	120.9
C4—C3—C2	107.3 (3)	C7—C13—C12	120.12 (17)
C4—C3—H3	126.3	C7—C13—C14	122.71 (17)
C2—C3—H3	126.3	C12—C13—C14	117.16 (16)
C3—C4—O1	109.1 (3)	C19—C14—C13	111.73 (15)
C3—C4—C5	135.6 (4)	C19—C14—C15	113.45 (16)
O1—C4—C5	115.3 (4)	C13—C14—C15	107.20 (15)
C1'—O1'—C4'	102.4 (6)	C19—C14—H14	108.1
C2'—C1'—O1'	113.2 (8)	C13—C14—H14	108.1
C2'—C1'—H1'	123.4	C15—C14—H14	108.1
O1'—C1'—H1'	123.4	C16—C15—C18	102.73 (17)
C1'—C2'—C3'	105.3 (7)	C16—C15—C14	119.19 (16)
C1'—C2'—H2'	127.3	C18—C15—C14	112.65 (16)
C3'—C2'—H2'	127.3	C16—C15—H15	107.2
C4'—C3'—C2'	104.3 (7)	C18—C15—H15	107.2
C4'—C3'—H3'	127.9	C14—C15—H15	107.2
C2'—C3'—H3'	127.9	O5—C16—O4	120.97 (19)
C3'—C4'—O1'	114.9 (8)	O5—C16—C15	129.9 (2)
C3'—C4'—C5	133.9 (10)	O4—C16—C15	109.12 (17)
O1'—C4'—C5	111.2 (8)	O4—C17—C18	103.72 (15)
C9—O2—C10	105.20 (15)	O4—C17—H17A	111.0
C11—O3—C10	105.14 (14)	C18—C17—H17A	111.0
C16—O4—C17	109.59 (16)	O4—C17—H17B	111.0
C23—O6—C27	117.80 (15)	C18—C17—H17B	111.0
C22—O7—C26	112.03 (15)	H17A—C17—H17B	109.0
C21—O8—C25	115.83 (14)	C15—C18—C17	101.01 (16)
C6—N1—C5	114.47 (17)	C15—C18—C6	110.41 (17)
C6—N1—H1	119 (2)	C17—C18—C6	120.64 (16)
C5—N1—H1	112 (2)	C15—C18—H18	108.0
N1—C5—C4'	111.2 (5)	C17—C18—H18	108.0
N1—C5—C4	110.5 (2)	C6—C18—H18	108.0
N1—C5—H5A	109.6	C24—C19—C20	119.56 (17)
C4'—C5—H5A	109.9	C24—C19—C14	119.99 (16)
C4—C5—H5A	109.4	C20—C19—C14	120.45 (16)
N1—C5—H5B	109.4	C21—C20—C19	120.65 (17)
C4'—C5—H5B	108.4	C21—C20—H20	119.7
C4—C5—H5B	109.7	C19—C20—H20	119.7
H5A—C5—H5B	108.3	O8—C21—C20	125.24 (16)
N1—C5—H5C	109.4	O8—C21—C22	114.73 (17)
C4'—C5—H5C	109.6	C20—C21—C22	120.03 (17)
C4—C5—H5C	109.0	O7—C22—C21	120.13 (17)
H5B—C5—H5C	108.8	O7—C22—C23	120.24 (16)
N1—C5—H5D	109.3	C21—C22—C23	119.57 (17)
C4'—C5—H5D	109.2	O6—C23—C22	114.70 (17)
C4—C5—H5D	110.5	O6—C23—C24	124.80 (17)
H5A—C5—H5D	107.6	C22—C23—C24	120.50 (16)
H5C—C5—H5D	108.2	C19—C24—C23	119.65 (17)
N1—C6—C18	114.55 (17)	C19—C24—H24	120.2
N1—C6—C7	109.34 (16)	C23—C24—H24	120.2
C18—C6—C7	109.71 (14)	O8—C25—H25A	109.5
N1—C6—H6	107.7	O8—C25—H25B	109.5
C18—C6—H6	107.7	H25A—C25—H25B	109.5
C7—C6—H6	107.7	O8—C25—H25C	109.5
C13—C7—C8	120.00 (17)	H25A—C25—H25C	109.5
C13—C7—C6	124.32 (16)	H25B—C25—H25C	109.5
C8—C7—C6	115.65 (16)	O7—C26—H26A	109.5
C9—C8—C7	118.42 (17)	O7—C26—H26B	109.5
C9—C8—H8	120.8	H26A—C26—H26B	109.5
C7—C8—H8	120.8	O7—C26—H26C	109.5
C8—C9—C11	121.44 (18)	H26A—C26—H26C	109.5
C8—C9—O2	128.97 (17)	H26B—C26—H26C	109.5
C11—C9—O2	109.57 (17)	O6—C27—H27A	109.5
O2—C10—O3	107.78 (15)	O6—C27—H27B	109.5
O2—C10—H10A	110.2	H27A—C27—H27B	109.5
O3—C10—H10A	110.2	O6—C27—H27C	109.5
O2—C10—H10B	110.2	H27A—C27—H27C	109.5
O3—C10—H10B	110.2	H27B—C27—H27C	109.5
C4—O1—C1—C2	−0.1 (2)	C7—C13—C14—C19	103.5 (2)
O1—C1—C2—C3	0.0 (2)	C12—C13—C14—C19	−75.1 (2)
C1—C2—C3—C4	0.1 (3)	C7—C13—C14—C15	−21.3 (2)
C2—C3—C4—O1	−0.2 (4)	C12—C13—C14—C15	160.05 (17)
C2—C3—C4—C5	−177.2 (5)	C19—C14—C15—C16	49.7 (2)
C1—O1—C4—C3	0.2 (3)	C13—C14—C15—C16	173.51 (18)
C1—O1—C4—C5	177.9 (3)	C19—C14—C15—C18	−70.7 (2)
C4'—O1'—C1'—C2'	0.0 (3)	C13—C14—C15—C18	53.1 (2)
O1'—C1'—C2'—C3'	0.0 (3)	C17—O4—C16—O5	176.9 (2)
C1'—C2'—C3'—C4'	0.0 (5)	C17—O4—C16—C15	−2.7 (2)
C2'—C3'—C4'—O1'	0.0 (7)	C18—C15—C16—O5	160.0 (2)
C2'—C3'—C4'—C5	−176.7 (12)	C14—C15—C16—O5	34.7 (4)
C1'—O1'—C4'—C3'	0.0 (6)	C18—C15—C16—O4	−20.5 (2)
C1'—O1'—C4'—C5	177.4 (9)	C14—C15—C16—O4	−145.80 (18)
C6—N1—C5—C4'	−81.7 (5)	C16—O4—C17—C18	24.8 (2)
C6—N1—C5—C4	−80.5 (3)	C16—C15—C18—C17	33.8 (2)
C3'—C4'—C5—N1	115.8 (10)	C14—C15—C18—C17	163.25 (17)
O1'—C4'—C5—N1	−61.0 (8)	C16—C15—C18—C6	162.55 (16)
C3'—C4'—C5—C4	58 (30)	C14—C15—C18—C6	−68.0 (2)
O1'—C4'—C5—C4	−119 (30)	O4—C17—C18—C15	−35.8 (2)
C3—C4—C5—N1	−47.2 (6)	O4—C17—C18—C6	−157.70 (18)
O1—C4—C5—N1	136.0 (3)	N1—C6—C18—C15	−79.7 (2)
C3—C4—C5—C4'	75 (30)	C7—C6—C18—C15	43.7 (2)
O1—C4—C5—C4'	−102 (30)	N1—C6—C18—C17	37.5 (3)
C5—N1—C6—C18	−88.4 (2)	C7—C6—C18—C17	160.88 (19)
C5—N1—C6—C7	148.05 (17)	C13—C14—C19—C24	144.26 (17)
N1—C6—C7—C13	112.7 (2)	C15—C14—C19—C24	−94.4 (2)
C18—C6—C7—C13	−13.7 (3)	C13—C14—C19—C20	−36.7 (2)
N1—C6—C7—C8	−65.2 (2)	C15—C14—C19—C20	84.6 (2)
C18—C6—C7—C8	168.40 (17)	C24—C19—C20—C21	1.9 (3)
C13—C7—C8—C9	0.5 (3)	C14—C19—C20—C21	−177.17 (18)
C6—C7—C8—C9	178.49 (19)	C25—O8—C21—C20	−1.4 (2)
C7—C8—C9—C11	0.5 (3)	C25—O8—C21—C22	178.75 (15)
C7—C8—C9—O2	−177.89 (19)	C19—C20—C21—O8	178.27 (17)
C10—O2—C9—C8	−171.2 (2)	C19—C20—C21—C22	−1.9 (3)
C10—O2—C9—C11	10.3 (2)	C26—O7—C22—C21	83.0 (2)
C9—O2—C10—O3	−15.8 (2)	C26—O7—C22—C23	−99.73 (19)
C11—O3—C10—O2	15.3 (2)	O8—C21—C22—O7	−2.6 (2)
C10—O3—C11—C12	172.9 (2)	C20—C21—C22—O7	177.56 (16)
C10—O3—C11—C9	−9.0 (2)	O8—C21—C22—C23	−179.89 (16)
C8—C9—C11—C12	−1.2 (3)	C20—C21—C22—C23	0.3 (3)
O2—C9—C11—C12	177.42 (18)	C27—O6—C23—C22	−176.57 (16)
C8—C9—C11—O3	−179.50 (19)	C27—O6—C23—C24	3.8 (3)
O2—C9—C11—O3	−0.9 (2)	O7—C22—C23—O6	4.4 (2)
O3—C11—C12—C13	178.88 (18)	C21—C22—C23—O6	−178.29 (16)
C9—C11—C12—C13	0.9 (3)	O7—C22—C23—C24	−175.91 (18)
C8—C7—C13—C12	−0.8 (3)	C21—C22—C23—C24	1.4 (3)
C6—C7—C13—C12	−178.56 (18)	C20—C19—C24—C23	−0.2 (3)
C8—C7—C13—C14	−179.37 (18)	C14—C19—C24—C23	178.83 (17)
C6—C7—C13—C14	2.9 (3)	O6—C23—C24—C19	178.24 (17)
C11—C12—C13—C7	0.1 (3)	C22—C23—C24—C19	−1.4 (3)
C11—C12—C13—C14	178.72 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C25—H25A···O2i	0.98	2.60	3.268 (2)	126.
C26—H26C···O3ii	0.98	2.60	3.544 (3)	163.
C27—H27A···O1iii	0.98	2.54	3.487 (4)	164.
C27—H27B···O7iv	0.98	2.50	2.993 (2)	111.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C25—H25A⋯O2i	0.98	2.60	3.268 (2)	126
C26—H26C⋯O3ii	0.98	2.60	3.544 (3)	163
C27—H27A⋯O1iii	0.98	2.54	3.487 (4)	164
C27—H27B⋯O7iv	0.98	2.50	2.993 (2)	111

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .