Monosuccinate ester of melampomagnolide B.

THE TITLE MONOSUCCINATE DERIVATIVE OF MELAMPOMAGNOLIDE B [SYSTEMATIC NAME: 4-(((1aR,7aS,10aS,10bS,E)-1a-methyl-8-meth-yl-ene-9-oxo-1a,2,3,6,7,7a,8,9,10a,10b-deca-hydro-oxireno[2',3':9,10]cyclo-deca-[1,2-b]furan-5-yl)meth-oxy)-4-oxo-butan-oic acid], C19H24O7, was obtained from the reaction of melampomagnolide B with succinic anhydride under nucleophilic addition reaction conditions. The mol-ecule is built up from fused ten-, five- (lactone) and three-membered (epoxide) rings. The inter-nal double bond in the ten-membered ring has the cis geometry (i.e. it is the E isomer). The lactone ring has an envelope-type conformation, with the (chiral) C atom opposite the lactone O atoms as the flap atom. In the crystal, O-H⋯O hydrogen bonds link the mol-ecules into chains parallel to the b-axis direction.

Related literature

For the biological activity of similar compounds, see: Nasim et al. (2011 ▶). For the isolation of a similar compound, see: El-Feraly (1984 ▶). For the structures and syntheses of similar compounds, see: Gonzalez et al. (1988 ▶); Macias et al. (1992 ▶); Casimir et al. (1995 ▶). Refinement progress was checked using routines in PLATON (Spek, 2009 ▶) and by the R-tensor (Parkin, 2000 ▶) The crystal was placed directly into the cold stream of a liquid nitro­gen based cryostat, according to published methods, see: Hope (1994 ▶); Parkin & Hope (1998 ▶).

Experimental

Crystal data

C19H24O7

M = 364.38

Orthorhombic,

a = 8.7866 (2) Å

b = 9.6082 (2) Å

c = 21.0088 (5) Å

V = 1773.63 (7) Å3

Z = 4

Cu Kα radiation

μ = 0.87 mm−1

T = 90 K

0.21 × 0.20 × 0.18 mm

Data collection

Bruker X8 Proteum diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008a ▶) T min = 0.818, T max = 0.889

21766 measured reflections

3218 independent reflections

3204 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.062

S = 1.03

3218 reflections

240 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.15 e Å−3

Absolute structure: Flack parameter determined using 1346 quotients [(I +)−(I −)]/[(I +)+(I −)] (Parsons et al., 2013 ▶)

Absolute structure parameter: −0.02 (3)

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008b ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008b ▶); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008b ▶) and CIFFIX (Parkin, 2013 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814002815/sj5379sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814002815/sj5379Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814002815/sj5379Isup3.cml

CCDC reference:

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

C19H24O7	Dx = 1.365 Mg m−3
Mr = 364.38	Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, P212121	Cell parameters from 9822 reflections
a = 8.7866 (2) Å	θ = 5.5–68.3°
b = 9.6082 (2) Å	µ = 0.87 mm−1
c = 21.0088 (5) Å	T = 90 K
V = 1773.63 (7) Å3	Wedge, colourless
Z = 4	0.21 × 0.20 × 0.18 mm
F(000) = 776

Bruker X8 Proteum diffractometer	3218 independent reflections
Radiation source: fine-focus rotating anode	3204 reflections with I > 2σ(I)
Detector resolution: 5.6 pixels mm-1	Rint = 0.033
φ and ω scans	θmax = 68.2°, θmin = 5.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	h = −10→4
Tmin = 0.818, Tmax = 0.889	k = −11→11
21766 measured reflections	l = −24→25

Refinement on F2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.024	w = 1/[σ2(Fo2) + (0.0321P)2 + 0.4142P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.062	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.16 e Å−3
3218 reflections	Δρmin = −0.15 e Å−3
240 parameters	Extinction correction: SHELXL2013 (Sheldrick, 2008a), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.0033 (6)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack parameter determined using 1346 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.02 (3)

Experimental. The crystal was mounted with polyisobutene oil on the tip of a fine glass fibre, fastened in a copper mounting pin with electrical solder. It was placed directly into the cold stream of a liquid nitrogen based cryostat, according to published methods (Hope, 1994; Parkin & Hope, 1998). Diffraction data were collected with the crystal at 90K, which is standard practice in this laboratory for the majority of flash-cooled crystals.

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

Refinement. Refinement progress was checked using routines in Platon (Spek, 2009), by the R-tensor (Parkin, 2000), and with the IUCr utility checkCIF.

	x	y	z	Uiso*/Ueq
O1	0.20411 (13)	0.31754 (11)	0.44993 (5)	0.0191 (3)
O2	0.23859 (13)	0.11877 (11)	0.55661 (5)	0.0204 (3)
O3	0.26866 (16)	−0.07622 (12)	0.61342 (6)	0.0307 (3)
O4	0.73762 (12)	0.64045 (12)	0.64763 (5)	0.0201 (3)
O5	0.95459 (14)	0.52306 (14)	0.66681 (7)	0.0309 (3)
O6	0.98811 (14)	0.66939 (14)	0.83142 (6)	0.0290 (3)
O7	1.23791 (13)	0.70884 (13)	0.82130 (6)	0.0229 (3)
H7	1.238 (3)	0.690 (2)	0.8623 (12)	0.034*
C1	0.5239 (2)	0.60864 (17)	0.52307 (8)	0.0214 (4)
H1A	0.6171	0.6045	0.5002	0.026*
C2	0.3899 (2)	0.66538 (17)	0.48663 (8)	0.0248 (4)
H2A	0.4240	0.7463	0.4612	0.030*
H2B	0.3127	0.6990	0.5173	0.030*
C3	0.3147 (2)	0.55854 (17)	0.44177 (8)	0.0223 (3)
H3A	0.2483	0.6076	0.4110	0.027*
H3B	0.3944	0.5087	0.4175	0.027*
C4	0.22202 (19)	0.45571 (16)	0.47891 (7)	0.0184 (3)
C5	0.30221 (18)	0.33451 (16)	0.50515 (7)	0.0162 (3)
H5A	0.4138	0.3313	0.4958	0.019*
C6	0.25592 (17)	0.26798 (16)	0.56681 (7)	0.0167 (3)
H6A	0.1580	0.3090	0.5822	0.020*
C7	0.38020 (17)	0.28350 (17)	0.61809 (7)	0.0184 (3)
H7A	0.4809	0.2858	0.5960	0.022*
C8	0.3701 (2)	0.41277 (18)	0.66040 (8)	0.0227 (4)
H8A	0.4472	0.4042	0.6945	0.027*
H8B	0.2688	0.4134	0.6811	0.027*
C9	0.39325 (18)	0.55441 (17)	0.62692 (7)	0.0199 (3)
H9A	0.3006	0.5757	0.6019	0.024*
H9B	0.4034	0.6273	0.6600	0.024*
C10	0.52939 (18)	0.56347 (16)	0.58308 (8)	0.0190 (3)
C11	0.36737 (18)	0.14530 (18)	0.65197 (8)	0.0217 (4)
C12	0.28777 (19)	0.04748 (17)	0.60846 (8)	0.0220 (4)
C13	0.4154 (2)	0.1067 (2)	0.70887 (9)	0.0300 (4)
H13A	0.3994	0.0140	0.7231	0.036*
H13B	0.4660	0.1717	0.7356	0.036*
C14	0.68183 (18)	0.52273 (17)	0.60986 (8)	0.0223 (4)
H14A	0.6716	0.4390	0.6370	0.027*
H14B	0.7539	0.5015	0.5750	0.027*
C15	0.07576 (19)	0.50907 (18)	0.50694 (8)	0.0231 (4)
H15A	0.0156	0.4307	0.5230	0.035*
H15B	0.0178	0.5584	0.4741	0.035*
H15C	0.0986	0.5729	0.5420	0.035*
C16	0.87876 (18)	0.62669 (18)	0.67217 (7)	0.0197 (3)
C17	0.9271 (2)	0.75939 (19)	0.70422 (8)	0.0267 (4)
H17A	0.8544	0.7803	0.7389	0.032*
H17B	0.9210	0.8362	0.6729	0.032*
C18	1.0873 (2)	0.7560 (2)	0.73186 (8)	0.0249 (4)
H18A	1.1513	0.6947	0.7051	0.030*
H18B	1.1309	0.8509	0.7297	0.030*
C19	1.09495 (19)	0.70589 (17)	0.79952 (8)	0.0189 (3)

	U11	U22	U33	U12	U13	U23
O1	0.0226 (6)	0.0180 (5)	0.0165 (5)	−0.0031 (4)	−0.0027 (4)	−0.0021 (4)
O2	0.0256 (6)	0.0170 (5)	0.0188 (5)	−0.0029 (5)	−0.0005 (5)	0.0013 (4)
O3	0.0416 (7)	0.0206 (6)	0.0299 (6)	−0.0002 (5)	0.0045 (6)	0.0061 (5)
O4	0.0175 (6)	0.0213 (6)	0.0215 (5)	0.0006 (4)	−0.0039 (4)	−0.0023 (4)
O5	0.0225 (6)	0.0267 (7)	0.0436 (7)	0.0041 (5)	−0.0058 (6)	−0.0024 (6)
O6	0.0205 (6)	0.0381 (8)	0.0284 (6)	−0.0032 (5)	0.0045 (5)	0.0074 (6)
O7	0.0177 (6)	0.0311 (6)	0.0200 (6)	−0.0015 (5)	−0.0027 (4)	0.0018 (5)
C1	0.0225 (8)	0.0161 (7)	0.0256 (9)	−0.0040 (7)	0.0014 (7)	−0.0039 (6)
C2	0.0335 (9)	0.0170 (8)	0.0239 (8)	−0.0047 (7)	−0.0040 (7)	0.0013 (7)
C3	0.0296 (9)	0.0193 (8)	0.0182 (7)	−0.0033 (7)	−0.0028 (7)	0.0012 (6)
C4	0.0214 (8)	0.0178 (8)	0.0160 (7)	−0.0010 (7)	−0.0036 (6)	−0.0025 (6)
C5	0.0160 (7)	0.0170 (7)	0.0156 (7)	−0.0016 (6)	−0.0004 (6)	−0.0025 (6)
C6	0.0166 (7)	0.0164 (7)	0.0171 (7)	−0.0003 (6)	0.0005 (6)	−0.0002 (6)
C7	0.0151 (7)	0.0231 (8)	0.0170 (7)	−0.0003 (6)	−0.0010 (6)	0.0014 (6)
C8	0.0230 (8)	0.0296 (9)	0.0155 (7)	−0.0026 (7)	−0.0008 (6)	−0.0023 (6)
C9	0.0172 (7)	0.0240 (8)	0.0185 (7)	0.0007 (6)	−0.0021 (6)	−0.0051 (6)
C10	0.0166 (7)	0.0156 (7)	0.0248 (8)	−0.0011 (6)	−0.0012 (6)	−0.0050 (6)
C11	0.0155 (7)	0.0267 (9)	0.0227 (8)	0.0031 (6)	0.0026 (6)	0.0035 (7)
C12	0.0218 (8)	0.0225 (9)	0.0218 (8)	0.0022 (7)	0.0052 (7)	0.0042 (6)
C13	0.0246 (9)	0.0382 (10)	0.0272 (9)	−0.0007 (8)	−0.0031 (7)	0.0105 (8)
C14	0.0175 (8)	0.0197 (8)	0.0297 (8)	−0.0019 (7)	−0.0022 (6)	−0.0050 (7)
C15	0.0218 (8)	0.0232 (8)	0.0245 (8)	0.0049 (7)	−0.0040 (7)	−0.0010 (7)
C16	0.0170 (7)	0.0254 (9)	0.0166 (7)	−0.0004 (7)	0.0011 (6)	0.0049 (6)
C17	0.0277 (9)	0.0285 (9)	0.0238 (8)	0.0007 (8)	−0.0080 (7)	−0.0025 (7)
C18	0.0230 (8)	0.0338 (9)	0.0181 (8)	−0.0042 (7)	−0.0020 (6)	−0.0002 (7)
C19	0.0171 (7)	0.0191 (7)	0.0204 (8)	−0.0013 (6)	0.0001 (6)	−0.0024 (6)

O1—C5	1.4545 (18)	C7—C11	1.511 (2)
O1—C4	1.4691 (18)	C7—C8	1.530 (2)
O2—C12	1.357 (2)	C7—H7A	1.0000
O2—C6	1.4575 (19)	C8—C9	1.545 (2)
O3—C12	1.205 (2)	C8—H8A	0.9900
O4—C16	1.3495 (19)	C8—H8B	0.9900
O4—C14	1.4660 (19)	C9—C10	1.512 (2)
O5—C16	1.203 (2)	C9—H9A	0.9900
O6—C19	1.206 (2)	C9—H9B	0.9900
O7—C19	1.337 (2)	C10—C14	1.505 (2)
O7—H7	0.88 (2)	C11—C13	1.321 (2)
C1—C10	1.334 (2)	C11—C12	1.486 (2)
C1—C2	1.507 (2)	C13—H13A	0.9500
C1—H1A	0.9500	C13—H13B	0.9500
C2—C3	1.542 (2)	C14—H14A	0.9900
C2—H2A	0.9900	C14—H14B	0.9900
C2—H2B	0.9900	C15—H15A	0.9800
C3—C4	1.499 (2)	C15—H15B	0.9800
C3—H3A	0.9900	C15—H15C	0.9800
C3—H3B	0.9900	C16—C17	1.503 (2)
C4—C5	1.468 (2)	C17—C18	1.522 (2)
C4—C15	1.504 (2)	C17—H17A	0.9900
C5—C6	1.501 (2)	C17—H17B	0.9900
C5—H5A	1.0000	C18—C19	1.502 (2)
C6—C7	1.541 (2)	C18—H18A	0.9900
C6—H6A	1.0000	C18—H18B	0.9900
C5—O1—C4	60.30 (9)	C10—C9—C8	115.61 (13)
C12—O2—C6	110.19 (12)	C10—C9—H9A	108.4
C16—O4—C14	116.01 (12)	C8—C9—H9A	108.4
C19—O7—H7	109.5 (16)	C10—C9—H9B	108.4
C10—C1—C2	128.74 (16)	C8—C9—H9B	108.4
C10—C1—H1A	115.6	H9A—C9—H9B	107.4
C2—C1—H1A	115.6	C1—C10—C14	118.03 (15)
C1—C2—C3	113.86 (14)	C1—C10—C9	124.46 (15)
C1—C2—H2A	108.8	C14—C10—C9	117.48 (14)
C3—C2—H2A	108.8	C13—C11—C12	121.97 (16)
C1—C2—H2B	108.8	C13—C11—C7	130.49 (17)
C3—C2—H2B	108.8	C12—C11—C7	107.54 (13)
H2A—C2—H2B	107.7	O3—C12—O2	121.52 (16)
C4—C3—C2	110.68 (13)	O3—C12—C11	129.52 (16)
C4—C3—H3A	109.5	O2—C12—C11	108.92 (13)
C2—C3—H3A	109.5	C11—C13—H13A	120.0
C4—C3—H3B	109.5	C11—C13—H13B	120.0
C2—C3—H3B	109.5	H13A—C13—H13B	120.0
H3A—C3—H3B	108.1	O4—C14—C10	107.42 (12)
C5—C4—O1	59.36 (9)	O4—C14—H14A	110.2
C5—C4—C3	117.22 (14)	C10—C14—H14A	110.2
O1—C4—C3	115.97 (13)	O4—C14—H14B	110.2
C5—C4—C15	122.24 (14)	C10—C14—H14B	110.2
O1—C4—C15	112.27 (13)	H14A—C14—H14B	108.5
C3—C4—C15	116.31 (14)	C4—C15—H15A	109.5
O1—C5—C4	60.34 (9)	C4—C15—H15B	109.5
O1—C5—C6	118.69 (12)	H15A—C15—H15B	109.5
C4—C5—C6	122.12 (13)	C4—C15—H15C	109.5
O1—C5—H5A	114.9	H15A—C15—H15C	109.5
C4—C5—H5A	114.9	H15B—C15—H15C	109.5
C6—C5—H5A	114.9	O5—C16—O4	123.66 (15)
O2—C6—C5	108.69 (12)	O5—C16—C17	125.95 (15)
O2—C6—C7	105.78 (12)	O4—C16—C17	110.36 (14)
C5—C6—C7	111.72 (12)	C16—C17—C18	114.48 (15)
O2—C6—H6A	110.2	C16—C17—H17A	108.6
C5—C6—H6A	110.2	C18—C17—H17A	108.6
C7—C6—H6A	110.2	C16—C17—H17B	108.6
C11—C7—C8	115.82 (13)	C18—C17—H17B	108.6
C11—C7—C6	101.03 (12)	H17A—C17—H17B	107.6
C8—C7—C6	116.32 (13)	C19—C18—C17	114.15 (15)
C11—C7—H7A	107.7	C19—C18—H18A	108.7
C8—C7—H7A	107.7	C17—C18—H18A	108.7
C6—C7—H7A	107.7	C19—C18—H18B	108.7
C7—C8—C9	116.28 (13)	C17—C18—H18B	108.7
C7—C8—H8A	108.2	H18A—C18—H18B	107.6
C9—C8—H8A	108.2	O6—C19—O7	123.18 (15)
C7—C8—H8B	108.2	O6—C19—C18	125.75 (15)
C9—C8—H8B	108.2	O7—C19—C18	111.05 (14)
H8A—C8—H8B	107.4
C10—C1—C2—C3	−100.0 (2)	C7—C8—C9—C10	−47.66 (19)
C1—C2—C3—C4	75.03 (19)	C2—C1—C10—C14	−175.00 (15)
C5—O1—C4—C3	107.62 (16)	C2—C1—C10—C9	3.1 (3)
C5—O1—C4—C15	−115.31 (15)	C8—C9—C10—C1	128.93 (16)
C2—C3—C4—C5	−85.28 (17)	C8—C9—C10—C14	−53.01 (19)
C2—C3—C4—O1	−152.51 (14)	C8—C7—C11—C13	−34.8 (2)
C2—C3—C4—C15	72.17 (18)	C6—C7—C11—C13	−161.43 (18)
C4—O1—C5—C6	112.70 (16)	C8—C7—C11—C12	146.07 (14)
C3—C4—C5—O1	−105.53 (14)	C6—C7—C11—C12	19.48 (15)
C15—C4—C5—O1	98.46 (16)	C6—O2—C12—O3	171.71 (15)
O1—C4—C5—C6	−107.15 (15)	C6—O2—C12—C11	−10.25 (17)
C3—C4—C5—C6	147.32 (14)	C13—C11—C12—O3	−8.2 (3)
C15—C4—C5—C6	−8.7 (2)	C7—C11—C12—O3	170.97 (17)
C12—O2—C6—C5	143.08 (13)	C13—C11—C12—O2	173.94 (16)
C12—O2—C6—C7	22.97 (16)	C7—C11—C12—O2	−6.87 (17)
O1—C5—C6—O2	57.76 (17)	C16—O4—C14—C10	−175.73 (13)
C4—C5—C6—O2	128.95 (14)	C1—C10—C14—O4	99.00 (17)
O1—C5—C6—C7	174.11 (12)	C9—C10—C14—O4	−79.19 (17)
C4—C5—C6—C7	−114.70 (16)	C14—O4—C16—O5	−3.4 (2)
O2—C6—C7—C11	−25.13 (15)	C14—O4—C16—C17	174.58 (13)
C5—C6—C7—C11	−143.23 (13)	O5—C16—C17—C18	−0.4 (2)
O2—C6—C7—C8	−151.39 (13)	O4—C16—C17—C18	−178.27 (13)
C5—C6—C7—C8	90.51 (16)	C16—C17—C18—C19	−89.65 (18)
C11—C7—C8—C9	176.24 (14)	C17—C18—C19—O6	0.4 (3)
C6—C7—C8—C9	−65.30 (19)	C17—C18—C19—O7	−178.44 (14)

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7···O1i	0.88 (2)	1.91 (3)	2.7616 (16)	162 (2)
C6—H6A···O6ii	1.00	2.60	3.173 (2)	117
C7—H7A···O1iii	1.00	2.40	3.3293 (19)	154
C14—H14A···O7iv	0.99	2.51	3.418 (2)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H7⋯O1i	0.88 (2)	1.91 (3)	2.7616 (16)	162 (2)
C6—H6A⋯O6ii	1.00	2.60	3.173 (2)	117
C7—H7A⋯O1iii	1.00	2.40	3.3293 (19)	154
C14—H14A⋯O7iv	0.99	2.51	3.418 (2)	153

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