Secohellebrigeninamide.

The title compound, C(26)H(37)NO(5), was the reaction product of hellebrigenin with N,N-dimethyl-formamide. It consists of three cyclo-hexane rings (A, B and C), one five-membered ring (D) and one dihydro-pyran ring (E). The stereochemistry of the ring junctions is is A/B cis, B/C trans, C/D cis and C/E trans. The cyclo-hexane rings A, B and C have chair conformations. Both the five-membered ring D and the dihydro-pyran ring adopt an envelope conformation. Two orientations are found for the aldehyde group with occupancies of 0.608 (10) and 0.392 (10). In the crystal, short O-H⋯O hydrogen bonds and short C-H⋯O contacts involving the hy-droxy group, terminal methyl group and carbonyl group link the mol-ecules into a three-dimensional network.

Related literature

For previous isolation of hellebrigenin, see: Urscheler et al. (1955 ▶); Yang et al. (2010 ▶); Zhao et al. (2010 ▶). For the treatment of hellebrigenin with sodium hydroxide, see: Kupchan et al. (1969 ▶). For the stereochemistry of bufalin, see: Rohrer et al. (1982 ▶).

Experimental

Crystal data

C26H37NO5

M = 443.57

Monoclinic,

a = 6.6942 (1) Å

b = 16.0580 (4) Å

c = 10.9672 (3) Å

β = 98.693 (2)°

V = 1165.38 (5) Å3

Z = 2

Cu Kα radiation

μ = 0.70 mm−1

T = 291 K

0.38 × 0.30 × 0.25 mm

Data collection

Oxford Diffraction Gemini S Ultra Sapphire CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.673, T max = 1.000

3575 measured reflections

2534 independent reflections

2431 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.130

S = 1.04

2534 reflections

293 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.16 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: XPREP in SHELXTL (Sheldrick, 2008 ▶); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: XP in SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681200520X/vm2153sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681200520X/vm2153Isup2.hkl

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

C26H37NO5	F(000) = 480
Mr = 443.57	Dx = 1.264 Mg m−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54184 Å
a = 6.6942 (1) Å	Cell parameters from 1847 reflections
b = 16.0580 (4) Å	θ = 6.2–62.6°
c = 10.9672 (3) Å	µ = 0.70 mm−1
β = 98.693 (2)°	T = 291 K
V = 1165.38 (5) Å3	Block, colorless
Z = 2	0.38 × 0.30 × 0.25 mm

Oxford Diffraction Gemini S Ultra Sapphire CCD diffractometer	2534 independent reflections
Radiation source: fine-focus sealed tube	2431 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
ω scan	θmax = 62.7°, θmin = 5.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −2→7
Tmin = 0.673, Tmax = 1.000	k = −18→16
3575 measured reflections	l = −12→11

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0899P)2 + 0.1076P] where P = (Fo2 + 2Fc2)/3
2534 reflections	(Δ/σ)max < 0.001
293 parameters	Δρmax = 0.18 e Å−3
1 restraint	Δρmin = −0.16 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	0.3441 (4)	1.40909 (16)	0.1536 (2)	0.0750 (6)
H1A	0.4127	1.4495	0.1793	0.113*
O2	0.0185 (3)	1.30160 (16)	0.1275 (2)	0.0737 (7)
H2A	0.0758	1.3465	0.1413	0.111*
O3	−0.0767 (8)	1.1408 (4)	0.3299 (6)	0.1087 (18)	0.608 (10)
O3A	−0.0065 (11)	1.2140 (6)	0.4159 (9)	0.1087 (18)	0.39
O4	0.2368 (3)	0.91532 (13)	0.12249 (17)	0.0530 (5)
O5	0.5706 (4)	0.54857 (15)	0.2410 (3)	0.0815 (7)
N1	0.9026 (4)	0.56933 (19)	0.3016 (3)	0.0666 (7)
C1	0.3354 (5)	1.2767 (2)	0.3439 (3)	0.0618 (8)
H1B	0.2441	1.3234	0.3468	0.074*
H1C	0.3765	1.2577	0.4279	0.074*
C2	0.5202 (5)	1.3069 (3)	0.2931 (3)	0.0712 (9)
H2B	0.5820	1.3521	0.3440	0.085*
H2C	0.6177	1.2619	0.2968	0.085*
C3	0.4688 (5)	1.3362 (2)	0.1624 (3)	0.0674 (9)
H3A	0.5939	1.3489	0.1298	0.081*
C4	0.3537 (5)	1.2682 (2)	0.0838 (3)	0.0634 (8)
H4A	0.3137	1.2896	0.0010	0.076*
H4B	0.4445	1.2217	0.0784	0.076*
C5	0.1669 (4)	1.2363 (2)	0.1317 (3)	0.0560 (7)
C6	0.0671 (5)	1.1673 (2)	0.0493 (3)	0.0671 (9)
H6A	−0.0642	1.1554	0.0724	0.080*
H6B	0.0456	1.1868	−0.0354	0.080*
C7	0.1889 (6)	1.0873 (2)	0.0561 (3)	0.0644 (8)
H7A	0.3133	1.0969	0.0231	0.077*
H7B	0.1125	1.0450	0.0058	0.077*
C8	0.2392 (4)	1.05563 (19)	0.1893 (2)	0.0473 (6)
H8A	0.1111	1.0420	0.2177	0.057*
C9	0.3438 (4)	1.12326 (18)	0.2759 (2)	0.0483 (6)
H9A	0.4721	1.1361	0.2472	0.058*
C10	0.2204 (4)	1.2060 (2)	0.2691 (2)	0.0515 (7)
C11	0.3965 (5)	1.0893 (2)	0.4077 (2)	0.0599 (8)
H11A	0.4701	1.1314	0.4598	0.072*
H11B	0.2728	1.0772	0.4403	0.072*
C12	0.5241 (5)	1.0104 (2)	0.4113 (3)	0.0613 (8)
H12A	0.5511	0.9903	0.4955	0.074*
H12B	0.6528	1.0240	0.3857	0.074*
C13	0.4233 (4)	0.94111 (19)	0.3285 (2)	0.0497 (6)
C14	0.3650 (4)	0.97681 (19)	0.1972 (2)	0.0445 (6)
C15	0.5674 (4)	0.9822 (2)	0.1456 (3)	0.0545 (7)
H15A	0.5486	0.9665	0.0592	0.065*
H15B	0.6208	1.0384	0.1535	0.065*
C16	0.7123 (4)	0.9212 (2)	0.2229 (3)	0.0598 (8)
H16A	0.8179	0.9508	0.2760	0.072*
H16B	0.7739	0.8835	0.1704	0.072*
C17	0.5736 (4)	0.8739 (2)	0.2993 (3)	0.0520 (6)
H17A	0.6491	0.8492	0.3741	0.062*
C18	0.2473 (5)	0.9056 (3)	0.3841 (3)	0.0682 (9)
H18A	0.1603	0.9501	0.4018	0.102*
H18B	0.2976	0.8766	0.4590	0.102*
H18C	0.1727	0.8677	0.3267	0.102*
C19	0.0265 (6)	1.1947 (3)	0.3181 (4)	0.0756 (10)
H19A	−0.0214	1.2446	0.3458	0.091*	0.608 (10)
H19B	−0.0789	1.1699	0.2657	0.091*	0.392 (10)
C20	0.4571 (4)	0.8096 (2)	0.2173 (3)	0.0509 (7)
C21	0.2995 (4)	0.83593 (19)	0.1362 (3)	0.0533 (7)
H21A	0.2281	0.7961	0.0855	0.064*
C22	0.5116 (4)	0.7228 (2)	0.2182 (3)	0.0519 (7)
H22A	0.4238	0.6878	0.1682	0.062*
C23	0.6737 (4)	0.6871 (2)	0.2826 (3)	0.0533 (7)
H23A	0.7655	0.7195	0.3343	0.064*
C24	0.7095 (5)	0.5968 (2)	0.2728 (3)	0.0584 (7)
C25	0.9418 (7)	0.4814 (3)	0.2967 (6)	0.1014 (15)
H25A	0.8161	0.4518	0.2801	0.152*
H25B	1.0148	0.4634	0.3744	0.152*
H25C	1.0208	0.4703	0.2324	0.152*
C26	1.0793 (5)	0.6229 (3)	0.3278 (4)	0.0850 (12)
H26A	1.0369	0.6799	0.3291	0.127*
H26B	1.1632	0.6156	0.2649	0.127*
H26C	1.1543	0.6084	0.4065	0.127*

	U11	U22	U33	U12	U13	U23
O1	0.0879 (15)	0.0492 (13)	0.0877 (15)	−0.0031 (12)	0.0124 (12)	−0.0062 (12)
O2	0.0705 (12)	0.0510 (13)	0.0906 (16)	0.0170 (12)	−0.0169 (11)	−0.0032 (13)
O3	0.091 (3)	0.098 (4)	0.147 (4)	0.003 (3)	0.050 (3)	0.008 (3)
O3A	0.091 (3)	0.098 (4)	0.147 (4)	0.003 (3)	0.050 (3)	0.008 (3)
O4	0.0530 (10)	0.0431 (11)	0.0563 (10)	−0.0014 (9)	−0.0130 (8)	−0.0010 (9)
O5	0.0729 (14)	0.0478 (14)	0.122 (2)	−0.0068 (13)	0.0100 (13)	−0.0097 (15)
N1	0.0637 (15)	0.0555 (16)	0.0823 (17)	0.0165 (13)	0.0171 (12)	0.0104 (14)
C1	0.0785 (19)	0.0551 (19)	0.0496 (14)	0.0123 (15)	0.0023 (13)	−0.0106 (14)
C2	0.0645 (17)	0.062 (2)	0.080 (2)	−0.0001 (17)	−0.0106 (15)	−0.0223 (19)
C3	0.0655 (17)	0.060 (2)	0.079 (2)	−0.0063 (16)	0.0204 (15)	−0.0040 (17)
C4	0.085 (2)	0.0552 (18)	0.0507 (14)	0.0045 (16)	0.0126 (13)	−0.0032 (14)
C5	0.0621 (15)	0.0452 (16)	0.0545 (15)	0.0085 (14)	−0.0114 (12)	0.0027 (14)
C6	0.079 (2)	0.0498 (19)	0.0622 (17)	0.0052 (17)	−0.0229 (15)	0.0032 (16)
C7	0.088 (2)	0.0491 (18)	0.0469 (14)	0.0056 (16)	−0.0193 (13)	−0.0018 (14)
C8	0.0463 (12)	0.0452 (15)	0.0460 (13)	0.0063 (12)	−0.0065 (10)	0.0009 (12)
C9	0.0524 (13)	0.0479 (16)	0.0415 (13)	0.0067 (12)	−0.0027 (10)	−0.0028 (12)
C10	0.0534 (14)	0.0478 (16)	0.0516 (14)	0.0081 (13)	0.0027 (11)	0.0007 (13)
C11	0.0778 (18)	0.0543 (18)	0.0423 (13)	0.0158 (16)	−0.0083 (12)	−0.0046 (13)
C12	0.0705 (17)	0.0562 (19)	0.0494 (14)	0.0096 (16)	−0.0157 (13)	−0.0019 (14)
C13	0.0492 (13)	0.0487 (16)	0.0463 (13)	0.0076 (13)	−0.0091 (10)	0.0006 (12)
C14	0.0426 (12)	0.0424 (14)	0.0451 (13)	−0.0002 (12)	−0.0041 (10)	−0.0032 (11)
C15	0.0557 (14)	0.0477 (16)	0.0611 (15)	−0.0030 (14)	0.0123 (12)	−0.0072 (14)
C16	0.0442 (13)	0.0497 (18)	0.0839 (19)	−0.0017 (13)	0.0047 (12)	−0.0115 (16)
C17	0.0474 (12)	0.0474 (15)	0.0558 (14)	0.0046 (13)	−0.0097 (11)	−0.0012 (14)
C18	0.0688 (17)	0.076 (2)	0.0592 (16)	0.0125 (18)	0.0086 (13)	0.0127 (16)
C19	0.067 (2)	0.067 (2)	0.099 (3)	0.0136 (19)	0.0331 (19)	0.006 (2)
C20	0.0450 (12)	0.0463 (16)	0.0586 (16)	0.0016 (12)	−0.0012 (11)	0.0023 (13)
C21	0.0546 (14)	0.0414 (15)	0.0601 (16)	−0.0046 (13)	−0.0038 (12)	−0.0011 (13)
C22	0.0543 (14)	0.0408 (15)	0.0597 (14)	−0.0028 (13)	0.0054 (11)	−0.0013 (13)
C23	0.0528 (14)	0.0448 (17)	0.0614 (16)	0.0028 (13)	0.0059 (12)	−0.0001 (13)
C24	0.0641 (16)	0.0458 (17)	0.0671 (17)	0.0049 (15)	0.0159 (13)	0.0026 (14)
C25	0.097 (3)	0.056 (2)	0.158 (4)	0.024 (2)	0.041 (3)	0.012 (3)
C26	0.0605 (19)	0.081 (3)	0.112 (3)	0.0096 (19)	0.0097 (17)	0.012 (2)

O1—C3	1.432 (4)	C10—C19	1.489 (5)
O1—H1A	0.8200	C11—C12	1.525 (4)
O2—C5	1.440 (4)	C11—H11A	0.9700
O2—H2A	0.8200	C11—H11B	0.9700
O3—C19	1.127 (7)	C12—C13	1.528 (4)
O3A—C19	1.169 (10)	C12—H12A	0.9700
O4—C21	1.343 (4)	C12—H12B	0.9700
O4—C14	1.473 (3)	C13—C18	1.517 (5)
O5—C24	1.219 (4)	C13—C17	1.543 (4)
N1—C24	1.357 (4)	C13—C14	1.544 (4)
N1—C25	1.439 (5)	C14—C15	1.548 (4)
N1—C26	1.455 (5)	C15—C16	1.540 (5)
C1—C2	1.511 (5)	C15—H15A	0.9700
C1—C10	1.538 (5)	C15—H15B	0.9700
C1—H1B	0.9700	C16—C17	1.541 (5)
C1—H1C	0.9700	C16—H16A	0.9700
C2—C3	1.500 (5)	C16—H16B	0.9700
C2—H2B	0.9700	C17—C20	1.506 (4)
C2—H2C	0.9700	C17—H17A	0.9800
C3—C4	1.526 (5)	C18—H18A	0.9600
C3—H3A	0.9800	C18—H18B	0.9600
C4—C5	1.517 (5)	C18—H18C	0.9600
C4—H4A	0.9700	C19—H19A	0.9300
C4—H4B	0.9700	C19—H19B	0.9300
C5—C6	1.519 (4)	C20—C21	1.342 (4)
C5—C10	1.572 (4)	C20—C22	1.441 (4)
C6—C7	1.518 (5)	C21—H21A	0.9300
C6—H6A	0.9700	C22—C23	1.331 (4)
C6—H6B	0.9700	C22—H22A	0.9300
C7—C8	1.534 (4)	C23—C24	1.477 (4)
C7—H7A	0.9700	C23—H23A	0.9300
C7—H7B	0.9700	C25—H25A	0.9600
C8—C14	1.515 (4)	C25—H25B	0.9600
C8—C9	1.540 (4)	C25—H25C	0.9600
C8—H8A	0.9800	C26—H26A	0.9600
C9—C11	1.535 (4)	C26—H26B	0.9600
C9—C10	1.560 (4)	C26—H26C	0.9600
C9—H9A	0.9800
C3—O1—H1A	109.5	C13—C12—H12B	108.9
C5—O2—H2A	109.5	H12A—C12—H12B	107.7
C21—O4—C14	115.3 (2)	C18—C13—C12	109.6 (3)
C24—N1—C25	118.9 (3)	C18—C13—C17	113.0 (3)
C24—N1—C26	124.9 (3)	C12—C13—C17	113.0 (2)
C25—N1—C26	116.1 (3)	C18—C13—C14	114.3 (2)
C2—C1—C10	114.3 (3)	C12—C13—C14	108.1 (2)
C2—C1—H1B	108.7	C17—C13—C14	98.5 (2)
C10—C1—H1B	108.7	O4—C14—C8	104.82 (18)
C2—C1—H1C	108.7	O4—C14—C13	108.3 (2)
C10—C1—H1C	108.7	C8—C14—C13	115.1 (2)
H1B—C1—H1C	107.6	O4—C14—C15	107.6 (2)
C3—C2—C1	111.8 (3)	C8—C14—C15	116.2 (3)
C3—C2—H2B	109.3	C13—C14—C15	104.5 (2)
C1—C2—H2B	109.3	C16—C15—C14	106.0 (2)
C3—C2—H2C	109.3	C16—C15—H15A	110.5
C1—C2—H2C	109.3	C14—C15—H15A	110.5
H2B—C2—H2C	107.9	C16—C15—H15B	110.5
O1—C3—C2	111.6 (3)	C14—C15—H15B	110.5
O1—C3—C4	107.9 (3)	H15A—C15—H15B	108.7
C2—C3—C4	109.7 (3)	C15—C16—C17	103.4 (2)
O1—C3—H3A	109.2	C15—C16—H16A	111.1
C2—C3—H3A	109.2	C17—C16—H16A	111.1
C4—C3—H3A	109.2	C15—C16—H16B	111.1
C5—C4—C3	114.7 (3)	C17—C16—H16B	111.1
C5—C4—H4A	108.6	H16A—C16—H16B	109.0
C3—C4—H4A	108.6	C20—C17—C16	108.3 (2)
C5—C4—H4B	108.6	C20—C17—C13	107.9 (2)
C3—C4—H4B	108.6	C16—C17—C13	103.5 (3)
H4A—C4—H4B	107.6	C20—C17—H17A	112.2
O2—C5—C4	110.1 (3)	C16—C17—H17A	112.2
O2—C5—C6	105.8 (2)	C13—C17—H17A	112.2
C4—C5—C6	110.6 (3)	C13—C18—H18A	109.5
O2—C5—C10	108.2 (2)	C13—C18—H18B	109.5
C4—C5—C10	110.8 (2)	H18A—C18—H18B	109.5
C6—C5—C10	111.2 (3)	C13—C18—H18C	109.5
C7—C6—C5	113.8 (2)	H18A—C18—H18C	109.5
C7—C6—H6A	108.8	H18B—C18—H18C	109.5
C5—C6—H6A	108.8	O3—C19—O3A	83.9 (6)
C7—C6—H6B	108.8	O3—C19—C10	135.9 (5)
C5—C6—H6B	108.8	O3A—C19—C10	126.5 (6)
H6A—C6—H6B	107.7	O3—C19—H19A	112.1
C6—C7—C8	111.5 (3)	O3A—C19—H19A	49.4
C6—C7—H7A	109.3	C10—C19—H19A	112.1
C8—C7—H7A	109.3	O3—C19—H19B	47.2
C6—C7—H7B	109.3	O3A—C19—H19B	116.8
C8—C7—H7B	109.3	C10—C19—H19B	116.8
H7A—C7—H7B	108.0	H19A—C19—H19B	107.7
C14—C8—C7	111.8 (2)	C21—C20—C22	118.8 (3)
C14—C8—C9	110.88 (19)	C21—C20—C17	117.7 (3)
C7—C8—C9	111.6 (2)	C22—C20—C17	123.4 (2)
C14—C8—H8A	107.4	C20—C21—O4	125.0 (3)
C7—C8—H8A	107.4	C20—C21—H21A	117.5
C9—C8—H8A	107.4	O4—C21—H21A	117.5
C11—C9—C8	110.4 (2)	C23—C22—C20	127.3 (3)
C11—C9—C10	113.1 (2)	C23—C22—H22A	116.4
C8—C9—C10	112.5 (2)	C20—C22—H22A	116.4
C11—C9—H9A	106.8	C22—C23—C24	120.8 (3)
C8—C9—H9A	106.8	C22—C23—H23A	119.6
C10—C9—H9A	106.8	C24—C23—H23A	119.6
C19—C10—C1	106.9 (3)	O5—C24—N1	121.3 (3)
C19—C10—C9	111.3 (3)	O5—C24—C23	121.3 (3)
C1—C10—C9	112.6 (2)	N1—C24—C23	117.5 (3)
C19—C10—C5	107.4 (2)	N1—C25—H25A	109.5
C1—C10—C5	107.8 (3)	N1—C25—H25B	109.5
C9—C10—C5	110.6 (2)	H25A—C25—H25B	109.5
C12—C11—C9	111.5 (2)	N1—C25—H25C	109.5
C12—C11—H11A	109.3	H25A—C25—H25C	109.5
C9—C11—H11A	109.3	H25B—C25—H25C	109.5
C12—C11—H11B	109.3	N1—C26—H26A	109.5
C9—C11—H11B	109.3	N1—C26—H26B	109.5
H11A—C11—H11B	108.0	H26A—C26—H26B	109.5
C11—C12—C13	113.2 (2)	N1—C26—H26C	109.5
C11—C12—H12A	108.9	H26A—C26—H26C	109.5
C13—C12—H12A	108.9	H26B—C26—H26C	109.5
C11—C12—H12B	108.9
C10—C1—C2—C3	57.5 (4)	C7—C8—C14—C13	179.7 (2)
C1—C2—C3—O1	65.9 (4)	C9—C8—C14—C13	54.5 (3)
C1—C2—C3—C4	−53.7 (4)	C7—C8—C14—C15	57.1 (3)
O1—C3—C4—C5	−67.4 (4)	C9—C8—C14—C15	−68.1 (3)
C2—C3—C4—C5	54.5 (4)	C18—C13—C14—O4	−47.9 (3)
C3—C4—C5—O2	65.0 (3)	C12—C13—C14—O4	−170.2 (2)
C3—C4—C5—C6	−178.4 (3)	C17—C13—C14—O4	72.2 (2)
C3—C4—C5—C10	−54.7 (4)	C18—C13—C14—C8	69.0 (4)
O2—C5—C6—C7	−171.6 (3)	C12—C13—C14—C8	−53.3 (3)
C4—C5—C6—C7	69.2 (4)	C17—C13—C14—C8	−170.9 (2)
C10—C5—C6—C7	−54.3 (4)	C18—C13—C14—C15	−162.4 (3)
C5—C6—C7—C8	55.2 (4)	C12—C13—C14—C15	75.3 (3)
C6—C7—C8—C14	−178.7 (3)	C17—C13—C14—C15	−42.3 (3)
C6—C7—C8—C9	−53.8 (3)	O4—C14—C15—C16	−93.9 (3)
C14—C8—C9—C11	−53.4 (3)	C8—C14—C15—C16	149.1 (2)
C7—C8—C9—C11	−178.7 (3)	C13—C14—C15—C16	21.1 (3)
C14—C8—C9—C10	179.2 (2)	C14—C15—C16—C17	9.2 (3)
C7—C8—C9—C10	53.9 (3)	C15—C16—C17—C20	78.0 (3)
C2—C1—C10—C19	−170.2 (3)	C15—C16—C17—C13	−36.4 (3)
C2—C1—C10—C9	67.3 (4)	C18—C13—C17—C20	55.1 (3)
C2—C1—C10—C5	−55.0 (3)	C12—C13—C17—C20	−179.8 (2)
C11—C9—C10—C19	−59.4 (3)	C14—C13—C17—C20	−66.0 (3)
C8—C9—C10—C19	66.6 (3)	C18—C13—C17—C16	169.7 (2)
C11—C9—C10—C1	60.6 (3)	C12—C13—C17—C16	−65.2 (3)
C8—C9—C10—C1	−173.4 (2)	C14—C13—C17—C16	48.6 (3)
C11—C9—C10—C5	−178.6 (2)	C1—C10—C19—O3	−147.7 (7)
C8—C9—C10—C5	−52.7 (3)	C9—C10—C19—O3	−24.3 (8)
O2—C5—C10—C19	46.2 (3)	C5—C10—C19—O3	96.8 (7)
C4—C5—C10—C19	167.0 (3)	C1—C10—C19—O3A	−22.8 (8)
C6—C5—C10—C19	−69.6 (4)	C9—C10—C19—O3A	100.6 (7)
O2—C5—C10—C1	−68.6 (3)	C5—C10—C19—O3A	−138.3 (7)
C4—C5—C10—C1	52.2 (3)	C16—C17—C20—C21	−77.4 (3)
C6—C5—C10—C1	175.6 (2)	C13—C17—C20—C21	34.0 (4)
O2—C5—C10—C9	167.8 (2)	C16—C17—C20—C22	99.9 (3)
C4—C5—C10—C9	−71.4 (3)	C13—C17—C20—C22	−148.8 (3)
C6—C5—C10—C9	52.0 (3)	C22—C20—C21—O4	−177.6 (3)
C8—C9—C11—C12	55.2 (3)	C17—C20—C21—O4	−0.2 (5)
C10—C9—C11—C12	−177.7 (3)	C14—O4—C21—C20	5.0 (4)
C9—C11—C12—C13	−57.2 (4)	C21—C20—C22—C23	172.7 (3)
C11—C12—C13—C18	−71.4 (3)	C17—C20—C22—C23	−4.5 (5)
C11—C12—C13—C17	161.6 (3)	C20—C22—C23—C24	−179.5 (3)
C11—C12—C13—C14	53.8 (3)	C25—N1—C24—O5	−1.4 (5)
C21—O4—C14—C8	−166.9 (2)	C26—N1—C24—O5	173.2 (4)
C21—O4—C14—C13	−43.6 (3)	C25—N1—C24—C23	178.1 (4)
C21—O4—C14—C15	68.8 (3)	C26—N1—C24—C23	−7.3 (5)
C7—C8—C14—O4	−61.5 (3)	C22—C23—C24—O5	−24.2 (5)
C9—C8—C14—O4	173.3 (2)	C22—C23—C24—N1	156.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O5i	0.82	1.97	2.790 (3)	178
C25—H25C···O1ii	0.96	2.64	3.513 (3)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O5i	0.82	1.97	2.790 (3)	178
C25—H25C⋯O1ii	0.96	2.64	3.513 (3)	152

Symmetry codes: (i) ; (ii) .