(Z)-6-Hy-droxy-1a,5-dimethyl-8-[(morpholin-4-yl)meth-yl]-2,3,6,7,7a,8,10a,10b-octa-hydro-oxireno[2',3':9,10]cyclo-deca-[1,2-b]furan-9(1aH)-one.

The title compound, C(19)H(29)NO(5), was synthesized from 9α-hy-droxy-parthenolide (9α-hy-droxy-4,8-dimethyl-12-methylen-3,14-dioxatricyclo-[9.3.0.0(2),(4)]tetra-dec-7-en-13-one), which was isolated from the chloro-form extract of the aerial parts of Anvillea radiata. The mol-ecule is built up from two fused five- and ten-membered rings with the (morpholin-4-yl)methyl group as a substituent. The five-membered lactone ring has an envelope conformation, whereas the ten-membered and the morpholine rings display approximate chair-chair and chair conformations, respectively. The dihedral angle between the ten-membered ring and the lactone ring is 27.93 (6)°. The crystal structure is stabilized by weak inter-molecular C-H⋯O hydrogen-bond inter-actions. An intra-molecular O-H⋯N hydrogen bond also occurs.

Related literature

For background to the medicinal uses of the plant Anvillea radiata, see: Abdel Sattar et al. (1996 ▶); Bellakhdar (1997 ▶); El Hassany et al. (2004 ▶); Qureshi et al. (1990 ▶). For the reactivity of this sesquiterpene see: Der-Ren et al. (2006 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C19H29NO5

M = 351.43

Monoclinic,

a = 11.7539 (3) Å

b = 6.8304 (2) Å

c = 11.8585 (3) Å

β = 101.328 (2)°

V = 933.50 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.45 × 0.33 × 0.12 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

11514 measured reflections

2086 independent reflections

1987 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.095

S = 1.07

2086 reflections

229 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.13 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2 and SAINT (Bruker, 2005 ▶); data reduction: SAINT; 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 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811022616/zl2378sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811022616/zl2378Isup2.hkl

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

C19H29NO5	F(000) = 380
Mr = 351.43	Dx = 1.250 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 11515 reflections
a = 11.7539 (3) Å	θ = 1.8–26.4°
b = 6.8304 (2) Å	µ = 0.09 mm−1
c = 11.8585 (3) Å	T = 298 K
β = 101.328 (2)°	Prism, colourless
V = 933.50 (4) Å3	0.45 × 0.33 × 0.12 mm
Z = 2

Bruker APEXII CCD area-detector diffractometer	1987 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.022
graphite	θmax = 26.4°, θmin = 1.8°
φ and ω scans	h = −14→14
11514 measured reflections	k = −7→8
2086 independent reflections	l = −14→14

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.064P)2 + 0.0786P] where P = (Fo2 + 2Fc2)/3
2086 reflections	(Δ/σ)max < 0.001
229 parameters	Δρmax = 0.17 e Å−3
1 restraint	Δρmin = −0.13 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

	x	y	z	Uiso*/Ueq
C4	0.68147 (17)	0.6737 (3)	0.7681 (2)	0.0506 (5)
H4	0.7514	0.6984	0.8181	0.061*
C1	0.59711 (14)	0.3364 (3)	0.86650 (18)	0.0446 (4)
C2	0.56720 (18)	0.5347 (4)	0.9071 (2)	0.0602 (6)
H2A	0.6204	0.5665	0.9782	0.072*
H2B	0.4894	0.5311	0.9232	0.072*
C3	0.5735 (2)	0.6950 (4)	0.8181 (3)	0.0662 (7)
H3A	0.5056	0.6872	0.7569	0.079*
H3B	0.5736	0.8224	0.8543	0.079*
C5	0.68894 (16)	0.6245 (3)	0.66217 (19)	0.0490 (5)
C6	0.80378 (17)	0.5685 (3)	0.63035 (17)	0.0456 (5)
H6	0.7974	0.5963	0.5483	0.055*
C7	0.82776 (15)	0.3483 (3)	0.64773 (14)	0.0379 (4)
H7A	0.8859	0.3110	0.6039	0.045*
H7B	0.7572	0.2775	0.6160	0.045*
C8	0.86965 (12)	0.2824 (3)	0.77319 (13)	0.0298 (3)
H8	0.8879	0.4000	0.8206	0.036*
C11	0.97917 (13)	0.1537 (3)	0.79115 (13)	0.0339 (4)
H11	0.9816	0.0817	0.7202	0.041*
C12	0.96289 (15)	0.0110 (3)	0.88422 (15)	0.0392 (4)
C9	0.78383 (13)	0.1581 (3)	0.82571 (13)	0.0320 (3)
H9	0.7295	0.0892	0.7654	0.038*
C10	0.71981 (13)	0.2807 (3)	0.89708 (14)	0.0367 (4)
H10	0.7686	0.3785	0.9441	0.044*
C14	0.5874 (2)	0.6021 (6)	0.5617 (2)	0.0801 (9)
H14A	0.5162	0.6256	0.5876	0.120*
H14B	0.5870	0.4718	0.5313	0.120*
H14C	0.5950	0.6949	0.5028	0.120*
C13	0.51592 (17)	0.2541 (4)	0.7628 (2)	0.0627 (6)
H13A	0.5454	0.1310	0.7420	0.094*
H13B	0.5101	0.3440	0.6997	0.094*
H13C	0.4405	0.2349	0.7808	0.094*
C15	1.09185 (13)	0.2656 (3)	0.82863 (14)	0.0408 (4)
H15A	1.0922	0.3251	0.9030	0.049*
H15B	1.1562	0.1742	0.8378	0.049*
C16	1.14927 (17)	0.3355 (3)	0.64750 (16)	0.0451 (4)
H16A	1.0909	0.2467	0.6069	0.054*
H16B	1.2201	0.2617	0.6734	0.054*
C17	1.1711 (2)	0.4972 (4)	0.5678 (2)	0.0615 (6)
H17A	1.1966	0.4405	0.5019	0.074*
H17B	1.0992	0.5669	0.5398	0.074*
C19	1.19698 (17)	0.5597 (4)	0.80346 (19)	0.0526 (5)
H19A	1.2686	0.4910	0.8339	0.063*
H19B	1.1701	0.6210	0.8672	0.063*
C18	1.2193 (2)	0.7138 (4)	0.7208 (3)	0.0680 (7)
H18A	1.1490	0.7893	0.6953	0.082*
H18B	1.2788	0.8022	0.7597	0.082*
N	1.10962 (11)	0.4195 (3)	0.74672 (12)	0.0387 (4)
O1	1.03350 (12)	−0.0969 (3)	0.93835 (13)	0.0577 (4)
O2	0.63581 (11)	0.1901 (3)	0.95455 (13)	0.0552 (4)
O3	0.85411 (10)	0.0191 (2)	0.90318 (10)	0.0397 (3)
O4	0.89640 (12)	0.6831 (3)	0.69114 (15)	0.0587 (4)
H4A	0.9564	0.6187	0.7018	0.088*
O5	1.25568 (15)	0.6306 (3)	0.62272 (16)	0.0699 (5)

	U11	U22	U33	U12	U13	U23
C4	0.0425 (9)	0.0284 (10)	0.0798 (14)	0.0016 (9)	0.0099 (9)	−0.0007 (10)
C1	0.0267 (8)	0.0497 (12)	0.0590 (11)	0.0022 (8)	0.0121 (7)	0.0057 (9)
C2	0.0395 (10)	0.0673 (16)	0.0785 (14)	0.0138 (11)	0.0234 (9)	−0.0065 (13)
C3	0.0552 (12)	0.0443 (13)	0.1029 (19)	0.0162 (12)	0.0243 (12)	−0.0044 (14)
C5	0.0392 (9)	0.0365 (11)	0.0678 (12)	0.0053 (8)	0.0020 (8)	0.0146 (9)
C6	0.0446 (9)	0.0423 (11)	0.0482 (9)	0.0010 (9)	0.0048 (7)	0.0152 (9)
C7	0.0378 (8)	0.0413 (10)	0.0334 (8)	0.0048 (8)	0.0042 (6)	0.0035 (7)
C8	0.0267 (7)	0.0312 (8)	0.0314 (7)	0.0029 (7)	0.0055 (5)	0.0007 (6)
C11	0.0291 (7)	0.0397 (10)	0.0333 (7)	0.0077 (7)	0.0071 (6)	0.0021 (7)
C12	0.0360 (8)	0.0408 (10)	0.0408 (8)	0.0094 (8)	0.0072 (6)	0.0056 (8)
C9	0.0277 (7)	0.0306 (9)	0.0363 (7)	0.0006 (7)	0.0029 (6)	0.0040 (7)
C10	0.0268 (7)	0.0444 (10)	0.0399 (8)	0.0005 (7)	0.0086 (6)	0.0033 (8)
C14	0.0522 (12)	0.100 (2)	0.0787 (16)	0.0113 (15)	−0.0105 (11)	0.0245 (18)
C13	0.0323 (9)	0.0586 (15)	0.0895 (16)	−0.0032 (10)	−0.0064 (9)	0.0044 (13)
C15	0.0285 (7)	0.0589 (12)	0.0347 (8)	0.0033 (8)	0.0054 (6)	0.0019 (8)
C16	0.0464 (9)	0.0478 (11)	0.0451 (9)	−0.0003 (9)	0.0186 (7)	−0.0042 (9)
C17	0.0723 (14)	0.0625 (16)	0.0556 (11)	−0.0063 (13)	0.0270 (10)	0.0036 (12)
C19	0.0363 (9)	0.0637 (15)	0.0590 (11)	−0.0096 (10)	0.0120 (8)	−0.0182 (11)
C18	0.0537 (11)	0.0563 (15)	0.0977 (17)	−0.0141 (12)	0.0234 (12)	−0.0159 (14)
N	0.0299 (6)	0.0480 (9)	0.0392 (7)	0.0003 (7)	0.0093 (5)	−0.0058 (7)
O1	0.0481 (7)	0.0642 (11)	0.0607 (8)	0.0229 (8)	0.0098 (6)	0.0236 (8)
O2	0.0364 (6)	0.0698 (11)	0.0645 (8)	0.0062 (8)	0.0226 (6)	0.0214 (8)
O3	0.0344 (6)	0.0383 (7)	0.0469 (6)	0.0060 (6)	0.0096 (5)	0.0122 (6)
O4	0.0453 (7)	0.0417 (8)	0.0877 (10)	−0.0077 (7)	0.0099 (7)	0.0103 (8)
O5	0.0682 (10)	0.0662 (12)	0.0845 (11)	−0.0174 (10)	0.0375 (9)	0.0003 (10)

C4—C5	1.320 (3)	C9—C10	1.495 (2)
C4—C3	1.509 (3)	C9—H9	0.9800
C4—H4	0.9300	C10—O2	1.444 (2)
C1—O2	1.452 (3)	C10—H10	0.9800
C1—C10	1.466 (2)	C14—H14A	0.9600
C1—C2	1.503 (4)	C14—H14B	0.9600
C1—C13	1.509 (3)	C14—H14C	0.9600
C2—C3	1.533 (4)	C13—H13A	0.9600
C2—H2A	0.9700	C13—H13B	0.9600
C2—H2B	0.9700	C13—H13C	0.9600
C3—H3A	0.9700	C15—N	1.473 (3)
C3—H3B	0.9700	C15—H15A	0.9700
C5—C14	1.519 (3)	C15—H15B	0.9700
C5—C6	1.520 (3)	C16—N	1.465 (2)
C6—O4	1.418 (3)	C16—C17	1.509 (3)
C6—C7	1.537 (3)	C16—H16A	0.9700
C6—H6	0.9800	C16—H16B	0.9700
C7—C8	1.540 (2)	C17—O5	1.410 (3)
C7—H7A	0.9700	C17—H17A	0.9700
C7—H7B	0.9700	C17—H17B	0.9700
C8—C11	1.538 (2)	C19—N	1.467 (3)
C8—C9	1.540 (2)	C19—C18	1.496 (4)
C8—H8	0.9800	C19—H19A	0.9700
C11—C12	1.513 (2)	C19—H19B	0.9700
C11—C15	1.518 (2)	C18—O5	1.433 (3)
C11—H11	0.9800	C18—H18A	0.9700
C12—O1	1.198 (2)	C18—H18B	0.9700
C12—O3	1.342 (2)	O4—H4A	0.8200
C9—O3	1.459 (2)
C5—C4—C3	128.1 (2)	C8—C9—H9	110.7
C5—C4—H4	116.0	O2—C10—C1	59.83 (12)
C3—C4—H4	116.0	O2—C10—C9	119.60 (17)
O2—C1—C10	59.33 (11)	C1—C10—C9	125.82 (16)
O2—C1—C2	116.72 (19)	O2—C10—H10	113.6
C10—C1—C2	115.79 (19)	C1—C10—H10	113.6
O2—C1—C13	112.9 (2)	C9—C10—H10	113.6
C10—C1—C13	122.61 (19)	C5—C14—H14A	109.5
C2—C1—C13	116.52 (19)	C5—C14—H14B	109.5
C1—C2—C3	112.15 (19)	H14A—C14—H14B	109.5
C1—C2—H2A	109.2	C5—C14—H14C	109.5
C3—C2—H2A	109.2	H14A—C14—H14C	109.5
C1—C2—H2B	109.2	H14B—C14—H14C	109.5
C3—C2—H2B	109.2	C1—C13—H13A	109.5
H2A—C2—H2B	107.9	C1—C13—H13B	109.5
C4—C3—C2	111.12 (19)	H13A—C13—H13B	109.5
C4—C3—H3A	109.4	C1—C13—H13C	109.5
C2—C3—H3A	109.4	H13A—C13—H13C	109.5
C4—C3—H3B	109.4	H13B—C13—H13C	109.5
C2—C3—H3B	109.4	N—C15—C11	113.24 (13)
H3A—C3—H3B	108.0	N—C15—H15A	108.9
C4—C5—C14	125.7 (2)	C11—C15—H15A	108.9
C4—C5—C6	121.92 (18)	N—C15—H15B	108.9
C14—C5—C6	112.3 (2)	C11—C15—H15B	108.9
O4—C6—C5	111.44 (19)	H15A—C15—H15B	107.7
O4—C6—C7	111.71 (16)	N—C16—C17	109.68 (19)
C5—C6—C7	111.18 (17)	N—C16—H16A	109.7
O4—C6—H6	107.4	C17—C16—H16A	109.7
C5—C6—H6	107.4	N—C16—H16B	109.7
C7—C6—H6	107.4	C17—C16—H16B	109.7
C6—C7—C8	115.55 (16)	H16A—C16—H16B	108.2
C6—C7—H7A	108.4	O5—C17—C16	112.00 (19)
C8—C7—H7A	108.4	O5—C17—H17A	109.2
C6—C7—H7B	108.4	C16—C17—H17A	109.2
C8—C7—H7B	108.4	O5—C17—H17B	109.2
H7A—C7—H7B	107.5	C16—C17—H17B	109.2
C11—C8—C7	113.64 (13)	H17A—C17—H17B	107.9
C11—C8—C9	103.05 (13)	N—C19—C18	110.83 (18)
C7—C8—C9	116.19 (13)	N—C19—H19A	109.5
C11—C8—H8	107.9	C18—C19—H19A	109.5
C7—C8—H8	107.9	N—C19—H19B	109.5
C9—C8—H8	107.9	C18—C19—H19B	109.5
C12—C11—C15	109.82 (13)	H19A—C19—H19B	108.1
C12—C11—C8	104.29 (12)	O5—C18—C19	111.8 (2)
C15—C11—C8	114.26 (16)	O5—C18—H18A	109.3
C12—C11—H11	109.4	C19—C18—H18A	109.3
C15—C11—H11	109.4	O5—C18—H18B	109.3
C8—C11—H11	109.4	C19—C18—H18B	109.3
O1—C12—O3	121.22 (17)	H18A—C18—H18B	107.9
O1—C12—C11	127.88 (16)	C16—N—C19	108.64 (14)
O3—C12—C11	110.89 (14)	C16—N—C15	111.03 (17)
O3—C9—C10	107.07 (13)	C19—N—C15	109.89 (14)
O3—C9—C8	106.16 (11)	C10—O2—C1	60.83 (11)
C10—C9—C8	111.28 (15)	C12—O3—C9	111.20 (13)
O3—C9—H9	110.7	C6—O4—H4A	109.5
C10—C9—H9	110.7	C17—O5—C18	109.61 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···N	0.82	2.24	3.051 (2)	172
C2—H2B···O2i	0.97	2.51	3.324 (3)	142
C10—H10···O1ii	0.98	2.47	3.270 (2)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4A⋯N	0.82	2.24	3.051 (2)	172
C2—H2B⋯O2i	0.97	2.51	3.324 (3)	142
C10—H10⋯O1ii	0.98	2.47	3.270 (2)	138

Symmetry codes: (i) ; (ii) .