Stemofoline ethyl acetate solvate.

Crystals of the title compound, C(22)H(29)NO(5)·C(4)H(8)O(2), {[systematic name: (2R,3R,5R,5aS,6R,8aR,9S)-(5Z)-5-[3-butyl-tetra-hydro-6-methyl-2,5-methano-4,3,8a-[1]propan-yl[3]yl-idene-furo[3,2-f][1,4]oxazepin-7(5H)-yl-idene]-4-meth-oxy-3-methyl-furan-2(5H)-one ethyl acetate solvate} were isolated from the root extracts of Stemona aphylla (Stemonaceae). The structure closely resembles those of stemofoline derivatives which have previously been reported. Inter-molecular contacts are observed between some C-bonded H atoms and nearby O atoms, perhaps indicating weak inter-actions which could influence the packing of species within the unit cell.

Related literature

For the single-crystal X-ray structure and absolute configuration of stemofoline as the hydro­bromide monohydrate, see: Irie et al. (1970 ▶). For two stemofoline alkaloids with structural modifications in the butyl side chain, see: Seger et al. (2004 ▶). For the isolation of stemofoline from the root extracts of Stemona aphylla (Stemonaceae), see: Mungkornasawakul et al. (2009 ▶). For details of the weighting scheme used, see: Watkin (1994 ▶); Prince (1982 ▶).

Experimental

Crystal data

C22H29NO5·C4H8O2

M = 475.58

Orthorhombic,

a = 10.3908 (1) Å

b = 10.6549 (2) Å

c = 22.4143 (4) Å

V = 2481.55 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 200 K

0.45 × 0.08 × 0.06 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: integration via Gaussian method (Coppens, 1970 ▶) implemented in maXus (Mackay et al., 2000 ▶) T min = 0.976, T max = 0.996

41745 measured reflections

3209 independent reflections

2149 reflections with I > 2σ(I)

R int = 0.060

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.119

S = 0.91

3208 reflections

307 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.25 e Å−3

Data collection: COLLECT (Nonius, 2001 ▶).; cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶) in TEXSAN (Molecular Structure Corporation, 1997 ▶); software used to prepare material for publication: CRYSTALS.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809026889/sj2635sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809026889/sj2635Isup2.hkl

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

C22H29NO5·C4H8O2	F(000) = 1024
Mr = 475.58	Dx = 1.273 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 36203 reflections
a = 10.3908 (1) Å	θ = 2.6–27.5°
b = 10.6549 (2) Å	µ = 0.09 mm−1
c = 22.4143 (4) Å	T = 200 K
V = 2481.55 (7) Å3	Needle, colourless
Z = 4	0.45 × 0.08 × 0.06 mm

Nonius KappaCCD diffractometer	2149 reflections with I > 2σ(I)
graphite	Rint = 0.060
φ and ω scans	θmax = 27.5°, θmin = 2.6°
Absorption correction: integration via Gaussian method (Coppens, 1970) implemented in maXus (Mackay et al., 2000)	h = −11→13
Tmin = 0.976, Tmax = 0.996	k = −13→13
41745 measured reflections	l = −29→25
3209 independent reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032	H-atom parameters constrained
wR(F2) = 0.119	Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)] where Ai are the Chebychev coefficients listed below and x = F /Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)2]2 Ai are: 38.7 60.5 31.2 8.38
S = 0.91	(Δ/σ)max = 0.002
3208 reflections	Δρmax = 0.30 e Å−3
307 parameters	Δρmin = −0.25 e Å−3
0 restraints

	x	y	z	Uiso*/Ueq
O1	0.43611 (16)	0.73200 (17)	0.47018 (7)	0.0301
O2	0.27062 (18)	0.79684 (16)	0.52966 (7)	0.0295
O3	0.30052 (17)	0.82685 (17)	0.64855 (8)	0.0315
O4	0.3242 (2)	0.49666 (18)	0.65754 (9)	0.0430
O5	0.3409 (2)	0.9075 (2)	0.73957 (9)	0.0469
O6	0.4158 (3)	0.2904 (2)	0.50427 (12)	0.0612
O7	0.4878 (2)	0.1608 (2)	0.57490 (9)	0.0427
N4	0.25605 (19)	0.6497 (2)	0.35879 (8)	0.0278
C1	0.4196 (3)	0.5479 (3)	0.40840 (11)	0.0331
C2	0.4559 (2)	0.6861 (2)	0.41002 (10)	0.0302
C3	0.3504 (2)	0.7525 (2)	0.37202 (10)	0.0287
C5	0.1296 (2)	0.7117 (3)	0.35629 (11)	0.0344
C6	0.1362 (3)	0.8327 (3)	0.39472 (11)	0.0355
C7	0.2744 (2)	0.8344 (2)	0.41800 (10)	0.0286
C8	0.2994 (2)	0.7520 (2)	0.47146 (10)	0.0265
C9	0.2300 (2)	0.6269 (2)	0.46769 (10)	0.0257
C9a	0.2729 (2)	0.5612 (2)	0.40984 (10)	0.0290
C10	0.2550 (2)	0.5713 (2)	0.53031 (10)	0.0268
C11	0.2737 (2)	0.6909 (2)	0.56580 (10)	0.0267
C12	0.2931 (2)	0.7068 (2)	0.62431 (11)	0.0280
C13	0.3204 (2)	0.6191 (3)	0.67198 (11)	0.0326
C14	0.3440 (3)	0.6821 (3)	0.72309 (11)	0.0347
C15	0.3298 (2)	0.8144 (3)	0.70898 (11)	0.0346
C16	0.3825 (3)	0.6425 (3)	0.78503 (12)	0.0495
C17	0.1423 (3)	0.4895 (3)	0.55107 (12)	0.0376
C18	0.3966 (3)	0.8207 (3)	0.31649 (11)	0.0357
C19	0.4653 (3)	0.7364 (3)	0.27164 (11)	0.0377
C20	0.5063 (3)	0.8045 (3)	0.21512 (12)	0.0452
C21	0.5627 (4)	0.7165 (4)	0.16876 (13)	0.0574
C22	0.3592 (4)	0.4074 (3)	0.70266 (16)	0.0556
C23	0.6093 (4)	0.3409 (4)	0.55692 (18)	0.0651
C24	0.4940 (3)	0.2645 (3)	0.54151 (14)	0.0416
C25	0.3810 (3)	0.0762 (3)	0.56316 (15)	0.0440
C26	0.2641 (3)	0.1114 (3)	0.59907 (17)	0.0558
H11	0.4519	0.5013	0.4432	0.0396*
H12	0.4479	0.5081	0.3715	0.0395*
H21	0.5450	0.7060	0.3962	0.0365*
H911	0.2270	0.4811	0.4032	0.0338*
H51	0.0633	0.6534	0.3702	0.0410*
H52	0.1109	0.7355	0.3144	0.0413*
H61	0.0745	0.8283	0.4278	0.0416*
H62	0.1195	0.9067	0.3706	0.0420*
H71	0.3101	0.9183	0.4223	0.0337*
H91	0.1369	0.6445	0.4656	0.0306*
H101	0.3345	0.5243	0.5313	0.0325*
H161	0.3834	0.7165	0.8100	0.0738*
H162	0.3207	0.5819	0.8013	0.0742*
H163	0.4664	0.6037	0.7857	0.0738*
H171	0.1554	0.4602	0.5914	0.0551*
H172	0.0625	0.5382	0.5495	0.0547*
H173	0.1341	0.4163	0.5249	0.0551*
H181	0.4556	0.8879	0.3283	0.0420*
H182	0.3199	0.8577	0.2961	0.0419*
H191	0.5420	0.7010	0.2907	0.0449*
H192	0.4080	0.6653	0.2615	0.0455*
H201	0.5699	0.8696	0.2253	0.0540*
H202	0.4287	0.8439	0.1984	0.0544*
H211	0.5834	0.7639	0.1322	0.0857*
H212	0.6415	0.6757	0.1828	0.0859*
H213	0.4996	0.6521	0.1586	0.0860*
H221	0.3518	0.3231	0.6844	0.0821*
H222	0.4473	0.4219	0.7153	0.0819*
H223	0.3003	0.4131	0.7367	0.0818*
H231	0.6081	0.4193	0.5351	0.0959*
H232	0.6114	0.3581	0.5997	0.0961*
H233	0.6878	0.2943	0.5464	0.0963*
H251	0.4091	−0.0102	0.5747	0.0533*
H252	0.3601	0.0796	0.5197	0.0528*
H261	0.1959	0.0507	0.5919	0.0841*
H262	0.2843	0.1122	0.6421	0.0837*
H263	0.2342	0.1963	0.5874	0.0839*

	U11	U22	U33	U12	U13	U23
O1	0.0236 (7)	0.0391 (9)	0.0275 (8)	−0.0033 (7)	−0.0031 (7)	0.0015 (7)
O2	0.0370 (8)	0.0293 (8)	0.0223 (7)	−0.0010 (7)	−0.0001 (7)	0.0000 (7)
O3	0.0339 (9)	0.0344 (9)	0.0263 (8)	−0.0039 (7)	−0.0009 (7)	−0.0017 (7)
O4	0.0571 (12)	0.0361 (10)	0.0359 (9)	0.0023 (9)	−0.0096 (9)	0.0058 (8)
O5	0.0530 (12)	0.0514 (12)	0.0363 (10)	−0.0041 (10)	−0.0027 (9)	−0.0099 (9)
O6	0.0657 (15)	0.0521 (14)	0.0658 (15)	0.0054 (12)	−0.0062 (13)	0.0190 (12)
O7	0.0420 (10)	0.0406 (10)	0.0456 (10)	−0.0051 (9)	−0.0037 (8)	0.0086 (9)
N4	0.0241 (9)	0.0348 (10)	0.0246 (9)	−0.0017 (8)	−0.0019 (7)	0.0005 (8)
C1	0.0330 (12)	0.0360 (13)	0.0304 (11)	0.0083 (10)	0.0025 (10)	0.0004 (10)
C2	0.0248 (11)	0.0404 (14)	0.0255 (10)	−0.0014 (10)	0.0004 (9)	0.0027 (10)
C3	0.0278 (11)	0.0322 (11)	0.0262 (10)	0.0006 (9)	−0.0008 (9)	0.0007 (10)
C5	0.0268 (11)	0.0450 (13)	0.0314 (11)	0.0020 (10)	−0.0069 (9)	−0.0007 (11)
C6	0.0355 (12)	0.0406 (13)	0.0303 (11)	0.0113 (11)	−0.0043 (10)	0.0025 (11)
C7	0.0318 (12)	0.0289 (11)	0.0253 (10)	−0.0009 (10)	−0.0016 (9)	0.0019 (10)
C8	0.0257 (10)	0.0286 (11)	0.0252 (10)	0.0002 (9)	−0.0017 (9)	−0.0030 (10)
C9	0.0238 (10)	0.0282 (11)	0.0250 (10)	−0.0008 (9)	−0.0009 (8)	0.0005 (9)
C9a	0.0304 (12)	0.0301 (11)	0.0265 (10)	−0.0016 (9)	0.0023 (9)	−0.0003 (9)
C10	0.0262 (10)	0.0275 (11)	0.0267 (10)	−0.0010 (9)	−0.0006 (9)	−0.0006 (9)
C11	0.0217 (10)	0.0307 (11)	0.0275 (10)	−0.0019 (9)	0.0012 (8)	0.0023 (9)
C12	0.0245 (10)	0.0326 (11)	0.0269 (11)	−0.0017 (9)	0.0009 (9)	−0.0013 (10)
C13	0.0274 (11)	0.0401 (13)	0.0304 (11)	−0.0012 (10)	−0.0006 (9)	0.0026 (10)
C14	0.0305 (12)	0.0492 (15)	0.0245 (10)	−0.0014 (11)	−0.0005 (9)	0.0041 (10)
C15	0.0278 (12)	0.0490 (15)	0.0271 (11)	−0.0034 (11)	−0.0020 (9)	−0.0010 (11)
C16	0.0594 (19)	0.0608 (19)	0.0281 (12)	−0.0049 (16)	−0.0091 (12)	0.0073 (13)
C17	0.0400 (14)	0.0379 (13)	0.0350 (12)	−0.0111 (11)	−0.0010 (11)	0.0053 (11)
C18	0.0366 (13)	0.0434 (14)	0.0270 (11)	−0.0039 (12)	0.0030 (10)	0.0071 (11)
C19	0.0356 (13)	0.0450 (15)	0.0325 (12)	−0.0036 (12)	0.0009 (10)	0.0062 (11)
C20	0.0440 (15)	0.0642 (18)	0.0275 (11)	−0.0026 (14)	0.0045 (11)	0.0076 (13)
C21	0.0618 (19)	0.076 (2)	0.0344 (14)	−0.0067 (18)	0.0077 (14)	−0.0012 (15)
C22	0.071 (2)	0.0446 (16)	0.0517 (17)	0.0004 (16)	−0.0158 (17)	0.0136 (14)
C23	0.073 (2)	0.0541 (19)	0.068 (2)	−0.0221 (19)	0.0059 (19)	−0.0021 (18)
C24	0.0468 (16)	0.0331 (13)	0.0451 (14)	0.0039 (12)	0.0067 (12)	−0.0018 (12)
C25	0.0415 (15)	0.0349 (13)	0.0558 (17)	−0.0041 (12)	−0.0001 (13)	0.0016 (13)
C26	0.0461 (17)	0.0518 (18)	0.070 (2)	−0.0022 (15)	0.0117 (16)	0.0055 (16)

O1—C2	1.449 (3)	C10—H101	0.966
O1—C8	1.436 (3)	C11—C12	1.338 (3)
O2—C8	1.421 (3)	C12—C13	1.447 (3)
O2—C11	1.389 (3)	C13—C14	1.350 (4)
O3—C12	1.392 (3)	C14—C15	1.452 (4)
O3—C15	1.394 (3)	C14—C16	1.505 (3)
O4—C13	1.345 (3)	C16—H161	0.967
O4—C22	1.435 (3)	C16—H162	0.980
O5—C15	1.212 (3)	C16—H163	0.965
O6—C24	1.197 (4)	C17—H171	0.965
O7—C24	1.336 (4)	C17—H172	0.978
O7—C25	1.453 (3)	C17—H173	0.980
N4—C3	1.499 (3)	C18—C19	1.525 (4)
N4—C5	1.471 (3)	C18—H181	0.980
N4—C9a	1.493 (3)	C18—H182	1.000
C1—C2	1.520 (4)	C19—C20	1.521 (4)
C1—C9a	1.531 (3)	C19—H191	0.980
C1—H11	0.984	C19—H192	0.990
C1—H12	0.976	C20—C21	1.518 (5)
C2—C3	1.559 (3)	C20—H201	0.985
C2—H21	0.998	C20—H202	0.983
C3—C7	1.565 (3)	C21—H211	0.987
C3—C18	1.520 (3)	C21—H212	0.979
C5—C6	1.552 (4)	C21—H213	0.975
C5—H51	0.978	C22—H221	0.991
C5—H52	0.993	C22—H222	0.970
C6—C7	1.528 (3)	C22—H223	0.981
C6—H61	0.981	C23—C24	1.489 (5)
C6—H62	0.971	C23—H231	0.968
C7—C8	1.508 (3)	C23—H232	0.977
C7—H71	0.972	C23—H233	0.984
C8—C9	1.519 (3)	C25—C26	1.504 (4)
C9—C9a	1.539 (3)	C25—H251	1.000
C9—C10	1.545 (3)	C25—H252	0.999
C9—H91	0.986	C26—H261	0.973
C9a—H911	0.989	C26—H262	0.987
C10—C11	1.515 (3)	C26—H263	0.991
C10—C17	1.532 (3)
O1···O2i	3.489 (2)	O5···C22iv	3.375 (5)
O2···C25ii	3.277 (4)	O6···C10	3.477 (3)
O2···C2iii	3.543 (3)	O6···C1	3.485 (4)
O3···C26ii	3.250 (4)	O7···C16v	3.422 (3)
O3···C25ii	3.379 (4)	C2···C11i	3.594 (3)
O3···C5i	3.446 (3)	C5···C15iii	3.453 (3)
C2—O1—C8	102.09 (17)	C11—C12—C13	132.2 (2)
C8—O2—C11	104.91 (18)	C12—C13—O4	117.0 (2)
C12—O3—C15	107.7 (2)	C12—C13—C14	109.9 (2)
C13—O4—C22	118.7 (2)	O4—C13—C14	133.0 (2)
C24—O7—C25	116.6 (2)	C13—C14—C15	106.2 (2)
C3—N4—C5	105.30 (19)	C13—C14—C16	133.7 (3)
C3—N4—C9a	103.48 (17)	C15—C14—C16	120.0 (2)
C5—N4—C9a	114.66 (18)	C14—C15—O3	109.1 (2)
C2—C1—C9a	99.0 (2)	C14—C15—O5	131.5 (2)
C2—C1—H11	112.7	O3—C15—O5	119.5 (3)
C9a—C1—H11	111.7	C14—C16—H161	107.8
C2—C1—H12	111.5	C14—C16—H162	110.6
C9a—C1—H12	111.0	H161—C16—H162	109.2
H11—C1—H12	110.5	C14—C16—H163	112.0
C1—C2—O1	108.29 (19)	H161—C16—H163	109.4
C1—C2—C3	104.6 (2)	H162—C16—H163	107.8
O1—C2—C3	104.78 (18)	C10—C17—H171	111.1
C1—C2—H21	115.4	C10—C17—H172	109.6
O1—C2—H21	110.4	H171—C17—H172	109.0
C3—C2—H21	112.8	C10—C17—H173	109.7
C2—C3—N4	103.71 (19)	H171—C17—H173	108.3
C2—C3—C7	104.38 (18)	H172—C17—H173	109.1
N4—C3—C7	102.02 (18)	C3—C18—C19	114.0 (2)
C2—C3—C18	116.2 (2)	C3—C18—H181	109.0
N4—C3—C18	113.22 (19)	C19—C18—H181	108.5
C7—C3—C18	115.6 (2)	C3—C18—H182	108.1
N4—C5—C6	108.20 (19)	C19—C18—H182	107.7
N4—C5—H51	109.4	H181—C18—H182	109.5
C6—C5—H51	112.4	C18—C19—C20	113.5 (2)
N4—C5—H52	109.0	C18—C19—H191	108.6
C6—C5—H52	108.7	C20—C19—H191	108.6
H51—C5—H52	109.1	C18—C19—H192	108.7
C5—C6—C7	103.9 (2)	C20—C19—H192	110.0
C5—C6—H61	110.5	H191—C19—H192	107.1
C7—C6—H61	110.9	C19—C20—C21	112.6 (3)
C5—C6—H62	111.0	C19—C20—H201	109.3
C7—C6—H62	110.3	C21—C20—H201	109.6
H61—C6—H62	110.0	C19—C20—H202	106.9
C6—C7—C3	104.02 (19)	C21—C20—H202	108.7
C6—C7—C8	115.2 (2)	H201—C20—H202	109.7
C3—C7—C8	96.39 (18)	C20—C21—H211	109.6
C6—C7—H71	113.8	C20—C21—H212	112.1
C3—C7—H71	112.7	H211—C21—H212	108.2
C8—C7—H71	113.0	C20—C21—H213	109.6
C7—C8—O1	103.93 (19)	H211—C21—H213	108.2
C7—C8—O2	119.8 (2)	H212—C21—H213	108.9
O1—C8—O2	106.06 (17)	O4—C22—H221	106.9
C7—C8—C9	112.66 (18)	O4—C22—H222	109.8
O1—C8—C9	109.78 (19)	H221—C22—H222	109.7
O2—C8—C9	104.25 (18)	O4—C22—H223	110.5
C8—C9—C9a	107.95 (18)	H221—C22—H223	109.2
C8—C9—C10	101.88 (18)	H222—C22—H223	110.6
C9a—C9—C10	122.82 (19)	C24—C23—H231	110.1
C8—C9—H91	107.6	C24—C23—H232	110.4
C9a—C9—H91	109.3	H231—C23—H232	109.6
C10—C9—H91	106.4	C24—C23—H233	109.6
C9—C9a—C1	110.4 (2)	H231—C23—H233	108.9
C9—C9a—N4	108.94 (19)	H232—C23—H233	108.1
C1—C9a—N4	99.16 (19)	C23—C24—O7	111.2 (3)
C9—C9a—H911	112.3	C23—C24—O6	125.6 (3)
C1—C9a—H911	113.4	O7—C24—O6	123.3 (3)
N4—C9a—H911	111.9	O7—C25—C26	111.4 (3)
C9—C10—C11	100.13 (17)	O7—C25—H251	107.5
C9—C10—C17	111.4 (2)	C26—C25—H251	109.1
C11—C10—C17	114.6 (2)	O7—C25—H252	108.7
C9—C10—H101	111.4	C26—C25—H252	109.7
C11—C10—H101	108.3	H251—C25—H252	110.3
C17—C10—H101	110.6	C25—C26—H261	109.6
C10—C11—O2	111.99 (19)	C25—C26—H262	110.7
C10—C11—C12	129.8 (2)	H261—C26—H262	108.8
O2—C11—C12	118.2 (2)	C25—C26—H263	109.8
O3—C12—C11	120.5 (2)	H261—C26—H263	109.5
O3—C12—C13	107.1 (2)	H262—C26—H263	108.4
O1—C2—C1—C9a	75.1 (2)	C2—C3—N4—C5	147.5 (2)
O1—C2—C3—N4	−107.2 (2)	C2—C3—N4—C9a	26.8 (2)
O1—C2—C3—C7	−0.7 (2)	C2—C3—C7—C6	−146.3 (2)
O1—C2—C3—C18	127.9 (2)	C2—C3—C7—C8	−28.3 (2)
O1—C8—O2—C11	−77.4 (2)	C2—C3—C18—C19	59.5 (3)
O1—C8—C7—C3	49.8 (2)	C3—N4—C5—C6	−25.4 (2)
O1—C8—C7—C6	158.7 (2)	C3—N4—C9a—C9	65.3 (2)
O1—C8—C9—C10	72.6 (2)	C3—C2—O1—C8	31.6 (2)
O1—C8—C9—C9a	−57.9 (2)	C3—C2—C1—C9a	−36.3 (2)
O2—C8—O1—C2	179.6 (2)	C3—C7—C6—C5	23.2 (2)
O2—C8—C7—C3	167.9 (2)	C3—C7—C8—C9	−68.9 (2)
O2—C8—C7—C6	−83.2 (3)	C3—C18—C19—C20	177.6 (2)
O2—C8—C9—C10	−40.6 (2)	C5—N4—C3—C7	39.3 (2)
O2—C8—C9—C9a	−171.2 (2)	C5—N4—C3—C18	−85.6 (2)
O2—C11—C10—C9	−4.1 (2)	C5—N4—C9a—C9	−48.8 (2)
O2—C11—C10—C17	−123.5 (2)	C5—C6—C7—C8	−81.0 (2)
O2—C11—C12—O3	4.6 (3)	C6—C5—N4—C9a	87.6 (2)
O2—C11—C12—C13	−169.4 (2)	C6—C7—C3—C18	84.6 (2)
O3—C12—C11—C10	−176.2 (2)	C6—C7—C8—C9	39.9 (3)
O3—C12—C13—O4	−177.0 (2)	C7—C3—N4—C9a	−81.4 (2)
O3—C12—C13—C14	−0.2 (3)	C7—C3—C18—C19	−177.6 (2)
O3—C15—C14—C13	−1.4 (3)	C7—C8—O2—C11	165.6 (2)
O3—C15—C14—C16	176.9 (2)	C7—C8—C9—C10	−172.1 (2)
O4—C13—C12—C11	−2.4 (4)	C7—C8—C9—C9a	57.4 (2)
O4—C13—C14—C15	177.0 (2)	C8—O2—C11—C10	−21.4 (2)
O4—C13—C14—C16	−0.9 (5)	C8—O2—C11—C12	157.9 (2)
O5—C15—O3—C12	−179.8 (2)	C8—C7—C3—C18	−157.3 (2)
O5—C15—C14—C13	179.9 (3)	C8—C9—C10—C11	26.1 (2)
O5—C15—C14—C16	−1.9 (4)	C8—C9—C10—C17	147.8 (2)
O6—C24—O7—C25	1.4 (4)	C9—C8—O2—C11	38.5 (2)
N4—C3—C2—C1	6.7 (2)	C9—C10—C11—C12	176.6 (2)
N4—C3—C7—C6	−38.7 (2)	C10—C11—C12—C13	9.8 (4)
N4—C3—C7—C8	79.4 (2)	C11—C10—C9—C9a	146.8 (2)
N4—C3—C18—C19	−60.4 (3)	C11—C12—O3—C15	−176.0 (2)
N4—C5—C6—C7	0.6 (3)	C11—C12—C13—C14	174.4 (3)
N4—C9a—C1—C2	52.8 (2)	C12—O3—C15—C14	1.2 (2)
N4—C9a—C9—C8	−51.8 (2)	C12—C11—C10—C17	57.2 (3)
N4—C9a—C9—C10	−169.7 (2)	C12—C13—O4—C22	176.0 (2)
C1—C2—O1—C8	−79.7 (2)	C12—C13—C14—C15	0.9 (3)
C1—C2—C3—C7	113.1 (2)	C12—C13—C14—C16	−177.0 (3)
C1—C2—C3—C18	−118.2 (2)	C13—C12—O3—C15	−0.6 (2)
C1—C9a—N4—C3	−50.1 (2)	C14—C13—O4—C22	0.1 (4)
C1—C9a—N4—C5	−164.2 (2)	C17—C10—C9—C9a	−91.5 (2)
C1—C9a—C9—C8	56.1 (2)	C18—C3—N4—C9a	153.7 (2)
C1—C9a—C9—C10	−61.8 (3)	C18—C19—C20—C21	−174.5 (3)
C2—O1—C8—C7	−53.2 (2)	C23—C24—O7—C25	−178.5 (3)
C2—O1—C8—C9	67.5 (2)	C24—O7—C25—C26	−87.9 (3)
C2—C1—C9a—C9	−61.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H171···O4	0.97	2.33	3.046 (4)	130
C22—H222···O5v	0.97	2.43	3.374 (4)	165
C1—H11···O6	0.98	2.66	3.485 (4)	142
C10—H101···O6	0.97	2.70	3.477 (3)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H171⋯O4	0.97	2.33	3.046 (4)	130
C22—H222⋯O5i	0.97	2.43	3.374 (4)	165
C1—H11⋯O6	0.98	2.66	3.485 (4)	142
C10—H101⋯O6	0.97	2.70	3.477 (3)	138

Symmetry code: (i) .