De-acetyl-cinobufalactam monohydrate.

The title compound, C24H33NO4·H2O, the reaction product of de-acetyl-cinobufagin with ammonium acetate, consists of three cyclo-hexane rings (A, B and C), one five-membered ring (D), one six-membered lactone ring (E) and an epoxide ring (F). The stereochemistry of the ring junctures are A/B cis, B/C trans, C/D cis and D/F cis. Cyclo-hexane rings A, B and C have normal chair conformations. The five-membered ring D adopts an envelope conformation (with the C atom bearing the lactone ring as the flap) and the lactone ring E is planar. In the crystal, hy-droxy and water O-H⋯O and amine N-H⋯O hydrogen bonds involving carbonyl, hy-droxy and water O-atom acceptors link the mol-ecules into a three-dimensional network.

Related literature

For a previous isolation of de­acetyl­cinobufagin [cinobufagin systematic name: (3β,5β,15β,16β)-16-acet­oxy-3-hy­droxy-14,15-ep­oxy­bufa-20,22-dienolide] see: Li et al. (2007 ▶). For the biosynthesis of de­acetyl­cinobufagin, see: Zhan et al. (2003 ▶). For its pharmacological activity, see: Yu et al. (2008 ▶); Tian et al. (2013 ▶). For the stereochemistry of bufalin, see: Rohrer et al. (1982 ▶).

Experimental

Crystal data

C24H33NO4·H2O

M = 417.53

Monoclinic,

a = 8.0097 (2) Å

b = 12.1155 (4) Å

c = 11.3627 (3) Å

β = 95.077 (3)°

V = 1098.33 (5) Å3

Z = 2

Cu Kα radiation

μ = 0.71 mm−1

T = 290 K

0.40 × 0.32 × 0.10 mm

Data collection

Oxford Diffraction Gemini-S Ultra sapphire CCD diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.806, T max = 1.0

3289 measured reflections

2396 independent reflections

2261 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.081

S = 1.08

2396 reflections

280 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 e Å−3

Δρmin = −0.13 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); 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: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814010046/zs2298sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814010046/zs2298Isup2.hkl

CCDC reference: 1000729

Additional supporting information: crystallographic information; 3D view; checkCIF report

C24H33NO4·H2O	F(000) = 452
Mr = 417.53	Dx = 1.263 Mg m−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2yb	Cell parameters from 2374 reflections
a = 8.0097 (2) Å	θ = 3.9–62.8°
b = 12.1155 (4) Å	µ = 0.71 mm−1
c = 11.3627 (3) Å	T = 290 K
β = 95.077 (3)°	Plate, colorless
V = 1098.33 (5) Å3	0.40 × 0.32 × 0.10 mm
Z = 2

Oxford Diffraction Gemini-S Ultra sapphire CCD diffractometer	2396 independent reflections
Radiation source: fine-focus sealed tube	2261 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
ω scans	θmax = 62.8°, θmin = 3.9°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	h = −9→8
Tmin = 0.806, Tmax = 1.0	k = −8→13
3289 measured reflections	l = −11→13

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0421P)2 + 0.128P] where P = (Fo2 + 2Fc2)/3
2396 reflections	(Δ/σ)max < 0.001
280 parameters	Δρmax = 0.14 e Å−3
1 restraint	Δρmin = −0.13 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
N1	−0.2500 (2)	0.63824 (18)	0.52081 (16)	0.0396 (5)
H1A	−0.3296	0.6720	0.5520	0.048*
O1	0.5226 (2)	0.78557 (15)	−0.38275 (14)	0.0450 (4)
H1B	0.5728	0.8339	−0.4159	0.067*
O2	0.2223 (2)	0.53707 (14)	0.21889 (13)	0.0404 (4)
O3	0.3082 (2)	0.66560 (16)	0.44674 (14)	0.0506 (5)
H3A	0.3830	0.7042	0.4788	0.076*
O4	−0.3079 (2)	0.48508 (18)	0.62396 (15)	0.0529 (5)
C1	0.2137 (3)	0.8092 (2)	−0.2603 (2)	0.0375 (5)
H1C	0.2009	0.7931	−0.3442	0.045*
H1D	0.1184	0.8536	−0.2424	0.045*
C2	0.3714 (3)	0.8770 (2)	−0.2341 (2)	0.0430 (6)
H2A	0.3799	0.9003	−0.1521	0.052*
H2B	0.3653	0.9426	−0.2832	0.052*
C3	0.5255 (3)	0.8109 (2)	−0.2575 (2)	0.0410 (6)
H3B	0.6263	0.8537	−0.2327	0.049*
C4	0.5291 (3)	0.7026 (2)	−0.1897 (2)	0.0399 (6)
H4A	0.6233	0.6591	−0.2113	0.048*
H4B	0.5473	0.7185	−0.1058	0.048*
C5	0.3701 (3)	0.6345 (2)	−0.21181 (18)	0.0347 (5)
H5A	0.3617	0.6135	−0.2954	0.042*
C6	0.3824 (4)	0.5274 (2)	−0.1411 (2)	0.0465 (6)
H6A	0.4896	0.4928	−0.1504	0.056*
H6B	0.2951	0.4773	−0.1727	0.056*
C7	0.3649 (3)	0.5455 (2)	−0.0095 (2)	0.0449 (6)
H7A	0.3630	0.4745	0.0299	0.054*
H7B	0.4614	0.5862	0.0251	0.054*
C8	0.2052 (3)	0.6091 (2)	0.01045 (19)	0.0343 (5)
H8A	0.1104	0.5640	−0.0218	0.041*
C9	0.1961 (3)	0.71946 (19)	−0.05767 (19)	0.0305 (5)
H9A	0.2951	0.7624	−0.0287	0.037*
C10	0.2087 (3)	0.6997 (2)	−0.19199 (18)	0.0328 (5)
C11	0.0424 (3)	0.7867 (2)	−0.0302 (2)	0.0420 (6)
H11A	0.0466	0.8585	−0.0675	0.050*
H11B	−0.0581	0.7494	−0.0634	0.050*
C12	0.0323 (3)	0.8024 (2)	0.1027 (2)	0.0405 (6)
H12A	−0.0680	0.8441	0.1151	0.049*
H12B	0.1281	0.8452	0.1345	0.049*
C13	0.0287 (3)	0.69225 (19)	0.17083 (18)	0.0324 (5)
C14	0.1819 (3)	0.62930 (19)	0.13928 (18)	0.0320 (5)
C15	0.3140 (3)	0.6388 (2)	0.2355 (2)	0.0392 (5)
H15A	0.4314	0.6419	0.2177	0.047*
C16	0.2557 (3)	0.7099 (2)	0.33232 (19)	0.0387 (6)
H16A	0.3031	0.7840	0.3260	0.046*
C17	0.0623 (3)	0.71678 (19)	0.30680 (18)	0.0336 (5)
H17A	0.0313	0.7941	0.3181	0.040*
C18	0.0561 (3)	0.6373 (3)	−0.2475 (2)	0.0516 (7)
H18A	0.0675	0.6258	−0.3300	0.077*
H18B	−0.0433	0.6797	−0.2385	0.077*
H18C	0.0479	0.5673	−0.2090	0.077*
C19	−0.1342 (3)	0.6303 (3)	0.1395 (2)	0.0452 (6)
H19A	−0.1484	0.6179	0.0558	0.068*
H19B	−0.2264	0.6732	0.1630	0.068*
H19C	−0.1307	0.5607	0.1800	0.068*
C20	−0.0349 (3)	0.6490 (2)	0.38948 (18)	0.0329 (5)
C21	−0.1599 (3)	0.6964 (2)	0.44449 (19)	0.0358 (5)
H21A	−0.1854	0.7703	0.4301	0.043*
C22	−0.0037 (3)	0.5362 (2)	0.41596 (18)	0.0349 (5)
H22A	0.0805	0.4998	0.3800	0.042*
C23	−0.0930 (3)	0.4799 (2)	0.49229 (19)	0.0375 (5)
H23A	−0.0689	0.4058	0.5068	0.045*
C24	−0.2220 (3)	0.5307 (2)	0.55044 (19)	0.0379 (6)
O1W	0.3771 (3)	0.4443 (2)	0.5263 (2)	0.0555 (5)
H1WA	0.480 (5)	0.462 (3)	0.567 (3)	0.092 (13)*
H1WB	0.355 (5)	0.503 (4)	0.496 (3)	0.084 (14)*

	U11	U22	U33	U12	U13	U23
N1	0.0374 (10)	0.0467 (13)	0.0365 (10)	0.0049 (9)	0.0131 (8)	0.0015 (10)
O1	0.0544 (10)	0.0426 (11)	0.0413 (9)	−0.0053 (8)	0.0232 (8)	0.0012 (8)
O2	0.0541 (9)	0.0351 (9)	0.0335 (8)	0.0123 (8)	0.0119 (7)	0.0039 (8)
O3	0.0563 (10)	0.0580 (12)	0.0357 (9)	−0.0091 (9)	−0.0054 (7)	−0.0029 (9)
O4	0.0498 (10)	0.0619 (12)	0.0490 (10)	−0.0076 (9)	0.0154 (8)	0.0124 (10)
C1	0.0428 (12)	0.0421 (14)	0.0288 (12)	0.0056 (11)	0.0091 (9)	0.0046 (11)
C2	0.0593 (15)	0.0318 (13)	0.0403 (13)	−0.0022 (12)	0.0179 (11)	−0.0008 (11)
C3	0.0437 (13)	0.0431 (14)	0.0380 (13)	−0.0094 (11)	0.0139 (10)	−0.0045 (12)
C4	0.0373 (12)	0.0458 (15)	0.0379 (12)	0.0043 (11)	0.0105 (10)	0.0002 (12)
C5	0.0467 (12)	0.0323 (13)	0.0269 (10)	−0.0007 (11)	0.0132 (9)	−0.0032 (10)
C6	0.0635 (15)	0.0373 (15)	0.0422 (13)	0.0084 (12)	0.0240 (11)	0.0007 (12)
C7	0.0616 (15)	0.0407 (14)	0.0353 (12)	0.0193 (13)	0.0209 (11)	0.0068 (12)
C8	0.0421 (12)	0.0317 (13)	0.0304 (11)	0.0025 (10)	0.0100 (9)	0.0012 (10)
C9	0.0351 (11)	0.0301 (12)	0.0274 (11)	0.0008 (9)	0.0084 (8)	0.0013 (10)
C10	0.0342 (11)	0.0378 (13)	0.0273 (11)	−0.0027 (10)	0.0067 (8)	0.0021 (11)
C11	0.0512 (14)	0.0439 (16)	0.0330 (13)	0.0135 (12)	0.0156 (10)	0.0118 (11)
C12	0.0526 (14)	0.0336 (13)	0.0377 (13)	0.0144 (12)	0.0181 (11)	0.0054 (11)
C13	0.0390 (12)	0.0310 (12)	0.0287 (11)	0.0024 (10)	0.0105 (9)	0.0000 (10)
C14	0.0406 (11)	0.0262 (12)	0.0305 (11)	0.0025 (10)	0.0116 (9)	0.0036 (10)
C15	0.0346 (11)	0.0459 (15)	0.0379 (12)	0.0011 (11)	0.0080 (9)	0.0021 (12)
C16	0.0462 (13)	0.0370 (14)	0.0335 (12)	−0.0076 (11)	0.0065 (10)	−0.0030 (11)
C17	0.0444 (12)	0.0273 (12)	0.0306 (12)	0.0012 (10)	0.0117 (9)	−0.0019 (10)
C18	0.0508 (14)	0.0668 (19)	0.0370 (13)	−0.0149 (14)	0.0033 (10)	−0.0092 (14)
C19	0.0417 (12)	0.0595 (17)	0.0353 (12)	−0.0028 (13)	0.0082 (10)	−0.0001 (13)
C20	0.0382 (11)	0.0357 (13)	0.0258 (10)	0.0009 (10)	0.0076 (9)	−0.0025 (10)
C21	0.0391 (12)	0.0361 (13)	0.0332 (11)	0.0050 (11)	0.0088 (9)	0.0038 (11)
C22	0.0401 (12)	0.0357 (13)	0.0295 (11)	0.0019 (11)	0.0063 (9)	−0.0037 (11)
C23	0.0468 (12)	0.0336 (13)	0.0326 (11)	−0.0016 (11)	0.0058 (10)	0.0011 (11)
C24	0.0361 (12)	0.0457 (15)	0.0316 (11)	−0.0050 (11)	0.0010 (9)	0.0034 (12)
O1W	0.0558 (13)	0.0493 (13)	0.0618 (13)	0.0030 (10)	0.0073 (10)	−0.0124 (12)

O1—C3	1.454 (3)	C20—C22	1.417 (3)
O2—C14	1.456 (3)	C20—C21	1.354 (3)
O2—C15	1.439 (3)	C22—C23	1.356 (3)
O3—C16	1.435 (3)	C23—C24	1.416 (3)
O4—C24	1.256 (3)	C1—H1C	0.9700
O1—H1B	0.8200	C1—H1D	0.9700
O3—H3A	0.8200	C2—H2B	0.9700
O1W—H1WB	0.80 (5)	C2—H2A	0.9700
O1W—H1WA	0.93 (4)	C3—H3B	0.9800
N1—C24	1.359 (3)	C4—H4A	0.9700
N1—C21	1.371 (3)	C4—H4B	0.9700
N1—H1A	0.8600	C5—H5A	0.9800
C1—C2	1.514 (3)	C6—H6B	0.9700
C1—C10	1.539 (3)	C6—H6A	0.9700
C2—C3	1.515 (3)	C7—H7B	0.9700
C3—C4	1.521 (3)	C7—H7A	0.9700
C4—C5	1.520 (3)	C8—H8A	0.9800
C5—C10	1.548 (3)	C9—H9A	0.9800
C5—C6	1.525 (3)	C11—H11A	0.9700
C6—C7	1.530 (3)	C11—H11B	0.9700
C7—C8	1.527 (3)	C12—H12A	0.9700
C8—C14	1.512 (3)	C12—H12B	0.9700
C8—C9	1.543 (3)	C15—H15A	0.9800
C9—C10	1.557 (3)	C16—H16A	0.9800
C9—C11	1.531 (3)	C17—H17A	0.9800
C10—C18	1.525 (4)	C18—H18B	0.9600
C11—C12	1.531 (3)	C18—H18A	0.9600
C12—C13	1.544 (3)	C18—H18C	0.9600
C13—C19	1.520 (4)	C19—H19B	0.9600
C13—C14	1.515 (3)	C19—H19C	0.9600
C13—C17	1.573 (3)	C19—H19A	0.9600
C14—C15	1.457 (3)	C21—H21A	0.9300
C15—C16	1.504 (3)	C22—H22A	0.9300
C16—C17	1.553 (3)	C23—H23A	0.9300
C17—C20	1.514 (3)
C14—O2—C15	60.45 (15)	C3—C2—H2A	109.00
C3—O1—H1B	109.00	C1—C2—H2A	109.00
C16—O3—H3A	109.00	H2A—C2—H2B	108.00
H1WA—O1W—H1WB	99 (4)	C3—C2—H2B	109.00
C21—N1—C24	124.38 (19)	O1—C3—H3B	110.00
C21—N1—H1A	118.00	C4—C3—H3B	109.00
C24—N1—H1A	118.00	C2—C3—H3B	109.00
C2—C1—C10	115.27 (19)	C3—C4—H4B	109.00
C1—C2—C3	110.9 (2)	C5—C4—H4A	109.00
O1—C3—C4	108.16 (19)	C5—C4—H4B	109.00
C2—C3—C4	110.28 (19)	H4A—C4—H4B	108.00
O1—C3—C2	109.92 (18)	C3—C4—H4A	109.00
C3—C4—C5	114.00 (19)	C6—C5—H5A	107.00
C4—C5—C10	113.4 (2)	C10—C5—H5A	107.00
C6—C5—C10	111.9 (2)	C4—C5—H5A	107.00
C4—C5—C6	111.2 (2)	C5—C6—H6B	109.00
C5—C6—C7	112.69 (19)	C7—C6—H6A	109.00
C6—C7—C8	111.6 (2)	C7—C6—H6B	109.00
C9—C8—C14	109.93 (19)	H6A—C6—H6B	108.00
C7—C8—C14	113.71 (19)	C5—C6—H6A	109.00
C7—C8—C9	111.45 (19)	C6—C7—H7A	109.00
C8—C9—C11	111.21 (19)	C6—C7—H7B	109.00
C8—C9—C10	110.74 (18)	C8—C7—H7B	109.00
C10—C9—C11	113.87 (19)	H7A—C7—H7B	108.00
C5—C10—C18	109.6 (2)	C8—C7—H7A	109.00
C1—C10—C18	105.9 (2)	C7—C8—H8A	107.00
C1—C10—C5	107.88 (19)	C9—C8—H8A	107.00
C9—C10—C18	111.25 (19)	C14—C8—H8A	107.00
C1—C10—C9	111.63 (19)	C8—C9—H9A	107.00
C5—C10—C9	110.39 (18)	C10—C9—H9A	107.00
C9—C11—C12	112.38 (19)	C11—C9—H9A	107.00
C11—C12—C13	113.08 (19)	C9—C11—H11B	109.00
C14—C13—C17	104.82 (18)	C12—C11—H11A	109.00
C12—C13—C14	105.37 (18)	C9—C11—H11A	109.00
C14—C13—C19	113.1 (2)	H11A—C11—H11B	108.00
C17—C13—C19	113.08 (18)	C12—C11—H11B	109.00
C12—C13—C17	108.66 (18)	C11—C12—H12A	109.00
C12—C13—C19	111.3 (2)	C13—C12—H12A	109.00
O2—C14—C8	115.95 (19)	C13—C12—H12B	109.00
O2—C14—C15	59.19 (14)	H12A—C12—H12B	108.00
C8—C14—C13	118.86 (19)	C11—C12—H12B	109.00
O2—C14—C13	112.31 (17)	O2—C15—H15A	120.00
C13—C14—C15	109.41 (18)	C14—C15—H15A	120.00
C8—C14—C15	126.6 (2)	C16—C15—H15A	120.00
O2—C15—C16	113.50 (19)	O3—C16—H16A	109.00
O2—C15—C14	60.36 (14)	C15—C16—H16A	109.00
C14—C15—C16	110.0 (2)	C17—C16—H16A	109.00
C15—C16—C17	105.27 (18)	C16—C17—H17A	107.00
O3—C16—C17	113.38 (18)	C20—C17—H17A	107.00
O3—C16—C15	111.32 (19)	C13—C17—H17A	107.00
C16—C17—C20	114.47 (18)	C10—C18—H18B	109.00
C13—C17—C20	117.02 (19)	C10—C18—H18C	110.00
C13—C17—C16	104.74 (18)	C10—C18—H18A	109.00
C17—C20—C21	119.9 (2)	H18A—C18—H18C	109.00
C21—C20—C22	115.8 (2)	H18B—C18—H18C	109.00
C17—C20—C22	124.4 (2)	H18A—C18—H18B	109.00
N1—C21—C20	121.7 (2)	C13—C19—H19A	109.00
C20—C22—C23	121.9 (2)	C13—C19—H19B	109.00
C22—C23—C24	121.9 (2)	H19A—C19—H19B	109.00
O4—C24—C23	125.8 (2)	H19A—C19—H19C	109.00
O4—C24—N1	119.9 (2)	C13—C19—H19C	109.00
N1—C24—C23	114.4 (2)	H19B—C19—H19C	109.00
C2—C1—H1C	108.00	C20—C21—H21A	119.00
C10—C1—H1C	108.00	N1—C21—H21A	119.00
C10—C1—H1D	108.00	C20—C22—H22A	119.00
C2—C1—H1D	108.00	C23—C22—H22A	119.00
H1C—C1—H1D	108.00	C22—C23—H23A	119.00
C1—C2—H2B	109.00	C24—C23—H23A	119.00
C15—O2—C14—C8	118.8 (2)	C10—C9—C11—C12	178.82 (19)
C15—O2—C14—C13	−100.0 (2)	C9—C11—C12—C13	−57.6 (3)
C14—O2—C15—C16	100.5 (2)	C11—C12—C13—C14	54.6 (2)
C24—N1—C21—C20	1.4 (3)	C11—C12—C13—C17	166.44 (19)
C21—N1—C24—O4	177.9 (2)	C11—C12—C13—C19	−68.4 (3)
C21—N1—C24—C23	−2.1 (3)	C12—C13—C14—O2	164.85 (17)
C10—C1—C2—C3	56.9 (3)	C12—C13—C14—C8	−55.1 (3)
C2—C1—C10—C5	−53.0 (2)	C12—C13—C14—C15	101.1 (2)
C2—C1—C10—C9	68.5 (3)	C17—C13—C14—O2	50.3 (2)
C2—C1—C10—C18	−170.3 (2)	C17—C13—C14—C8	−169.7 (2)
C1—C2—C3—O1	65.1 (2)	C17—C13—C14—C15	−13.5 (2)
C1—C2—C3—C4	−54.1 (2)	C19—C13—C14—O2	−73.4 (2)
O1—C3—C4—C5	−66.7 (2)	C19—C13—C14—C8	66.7 (3)
C2—C3—C4—C5	53.6 (3)	C19—C13—C14—C15	−137.1 (2)
C3—C4—C5—C6	−179.94 (18)	C12—C13—C17—C16	−89.8 (2)
C3—C4—C5—C10	−52.8 (2)	C12—C13—C17—C20	142.3 (2)
C4—C5—C6—C7	74.5 (3)	C14—C13—C17—C16	22.5 (2)
C10—C5—C6—C7	−53.5 (3)	C14—C13—C17—C20	−105.5 (2)
C4—C5—C10—C1	49.7 (2)	C19—C13—C17—C16	146.2 (2)
C4—C5—C10—C9	−72.6 (2)	C19—C13—C17—C20	18.2 (3)
C4—C5—C10—C18	164.56 (19)	O2—C14—C15—C16	−106.3 (2)
C6—C5—C10—C1	176.39 (18)	C8—C14—C15—O2	−101.1 (2)
C6—C5—C10—C9	54.2 (3)	C8—C14—C15—C16	152.6 (2)
C6—C5—C10—C18	−68.7 (2)	C13—C14—C15—O2	104.98 (19)
C5—C6—C7—C8	53.6 (3)	C13—C14—C15—C16	−1.3 (3)
C6—C7—C8—C9	−55.0 (3)	O2—C15—C16—O3	73.6 (2)
C6—C7—C8—C14	−180.0 (2)	O2—C15—C16—C17	−49.7 (2)
C7—C8—C9—C10	56.5 (2)	C14—C15—C16—O3	139.0 (2)
C7—C8—C9—C11	−175.82 (18)	C14—C15—C16—C17	15.8 (2)
C14—C8—C9—C10	−176.48 (19)	O3—C16—C17—C13	−145.25 (19)
C14—C8—C9—C11	−48.8 (3)	O3—C16—C17—C20	−15.8 (3)
C7—C8—C14—O2	−41.8 (3)	C15—C16—C17—C13	−23.3 (2)
C7—C8—C14—C13	179.6 (2)	C15—C16—C17—C20	106.2 (2)
C7—C8—C14—C15	27.8 (3)	C13—C17—C20—C21	−107.9 (2)
C9—C8—C14—O2	−167.51 (19)	C13—C17—C20—C22	72.7 (3)
C9—C8—C14—C13	53.9 (3)	C16—C17—C20—C21	129.0 (2)
C9—C8—C14—C15	−97.9 (3)	C16—C17—C20—C22	−50.4 (3)
C8—C9—C10—C1	−175.57 (19)	C17—C20—C21—N1	−179.4 (2)
C8—C9—C10—C5	−55.6 (3)	C22—C20—C21—N1	0.0 (3)
C8—C9—C10—C18	66.3 (3)	C17—C20—C22—C23	178.9 (2)
C11—C9—C10—C1	58.2 (3)	C21—C20—C22—C23	−0.5 (3)
C11—C9—C10—C5	178.21 (19)	C20—C22—C23—C24	−0.3 (4)
C11—C9—C10—C18	−59.9 (3)	C22—C23—C24—O4	−178.5 (2)
C8—C9—C11—C12	52.9 (3)	C22—C23—C24—N1	1.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O4i	0.93 (4)	1.79 (4)	2.710 (3)	170 (4)
O1W—H1WB···O3	0.80 (5)	2.07 (5)	2.867 (3)	170 (4)
N1—H1A···O1ii	0.86	2.00	2.839 (3)	165
O1—H1B···O1Wiii	0.82	1.90	2.690 (3)	161
O3—H3A···O1iv	0.82	2.09	2.868 (2)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O4i	0.93 (4)	1.79 (4)	2.710 (3)	170 (4)
O1W—H1WB⋯O3	0.80 (5)	2.07 (5)	2.867 (3)	170 (4)
N1—H1A⋯O1ii	0.86	2.00	2.839 (3)	165
O1—H1B⋯O1W iii	0.82	1.90	2.690 (3)	161
O3—H3A⋯O1iv	0.82	2.09	2.868 (2)	157

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