10α-Hy­droxy-4,9-dimethyl-13-[(pyrrol­idin-1-yl)meth­yl]-3,8,15-trioxatetra­cyclo­[10.3.0.02,4.07,9]penta­decan-14-one

Moumou, M.; Benharref, A.; Berraho, M.; Avignant, D.; Oudahmane, A.; Akssira, M.

doi:10.1107/S1600536811024688

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Pages o1842-o1843

doi:10.1107/S1600536811024688

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10α-Hydroxy-4,9-dimethyl-13-[(pyrrolidin-1-yl)methyl]-3,8,15-trioxatetracyclo[10.3.0.0^2,4.0^7,9]pentadecan-14-one

Mohamed Moumou,^a ^* Ahmed Benharref,^a Moha Berraho,^a Daniel Avignant,^b Abdelghani Oudahmane ^b and Mohamed Akssira ^c

^aLaboratoire de Chimie Biomoléculaire, Substances Naturelles et Réactivité, URAC 16, Faculté des Sciences Semlalia, BP 2390, Bd My Abdellah,40000 Marrakech, Morocco, ^bLaboratoire des Matériaux Inorganiques, Université Blaise Pascal, UMR CNRS 6002, 24 Avenue des Landais, 63177 Aubière, France, and ^cLaboratoire de Chimie Bioorganique et Analytique, URAC 22, BP 146, FSTM, Université Hassan II, Mohammedia-Casablanca 20810 Mohammedia, Morocco
^*Correspondence e-mail: mberraho@yahoo.fr

(Received 21 June 2011; accepted 23 June 2011; online 30 June 2011)

The title compound, C₁₉H₂₉NO₅, was synthesized from 9α-hydroxyparthenolide (9α-hydroxy-4,8-dimethyl-12-methylene-3,14-dioxatricyclo[9.3.0.0^2,4]tetradec-7-en-13-one), which was isolated from the chloroform extract of the aerial parts of Anvillea radiata. The molecule is built up from two fused five- and ten-membered rings with the (pyrrolidin-4-yl)methyl group as a substituent. The two five-membered ring display the same envelope conformations, whereas the ten-membered ring adopts an approximate chair–chair conformation. The dihedral angle between the ten-membered ring and the lactone ring is 21.81 (9)°. An intramolecular O—H⋯N hydrogen bond stabilizes the molecular conformation. In the crystal, intermolecular C—H⋯O interactions link the molecules into chains parallel to the c axis.

Related literature

For background to the medicinal uses of the plant Anvillea radiata, see: El Hassany et al. (2004 ). For reactivity of this sesquiterpene see: Der-Ren et al. (2006 ); Neelakantan et al. (2009 ); Neukirch et al. (2003 ). For ring puckering parameters, see: Cremer & Pople (1975 ). For conformations of ten-membered rings, see: Castaneda-Acosta et al. (1997 ). For related structures, see: Moumou et al. (2010 ); Watson & Zabel (1982 ).

Experimental

Crystal data

C₁₉H₂₉NO₅
M_r = 351.43
Orthorhombic, P 2₁ 2₁ 2₁
a = 8.0714 (2) Å
b = 10.4571 (3) Å
c = 21.5816 (8) Å
V = 1821.56 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.89 × 0.46 × 0.21 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
8707 measured reflections
2122 independent reflections
1660 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.098
S = 1.03
2122 reflections
229 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯N	0.82	2.04	2.851 (2)	172
C9—H9⋯O4ⁱ	0.98	2.38	3.260 (2)	149
C10—H10⋯O2ⁱⁱ	0.98	2.46	3.392 (3)	158
C19—H19B⋯O5ⁱⁱⁱ	0.97	2.59	3.357 (3)	136
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ ; (iii) $[-x+{\script{1\over 2}}, -y+1, z-{\script{1\over 2}}]$ .

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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811024688/om2443sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811024688/om2443Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811024688/om2443Isup3.cml

checkCIF report

Comment top

Our work lies within the framework of the valorization of medicinals plants and concerning the Anvillea radiata. The main constituent of the chloroform extract of aerial parts of this plant is 9α-hydroxypartenolide (El Hassany et al., 2004). The reactivity of this sesquiterpene lactone and its derivatives has been the subject of several studies (Neukirch et al., 2003; Der-Ren et al., 2006; Neelakantan et al., 2009), in order to prepare products with a high added value that can be used in the pharmacology industry. In this context, we have treated the 9α-hydroxypartenolide with one equivalent of meta-chloroperbenzoic acid (mCPBA), as we have done for its isomer the 9β-hydroxypartenolide (Moumou et al.,2010), and we got the 6β,7α-epoxy-9α-hydroxypartenolide in a yield of 75% (see Figure 3). This latter was treated with an equivalent of pyrrolodine and gives the title compound (I) in a yield of 95%. The molecule contains two fused rings which exhibit different conformations with a pyrolidin ring as a substituent to the lactone ring. The molecular structure of (I), Fig. 1, shows that the two five membered rings adopt an envelope conformation, as indicated by Cremer & Pople (1975) puckering parameters Q = 0.298 (2) Å and ϕ = 77.5 (4)° for the lactone ring and Q = 0.362 (3) Å, ϕ2 = 6.4 (6)° for the pyrolidin ring. The ten-membered ring displays an approximate chair-chair conformation, this is the typical conformation observed for other sesquiterpenes lactones (Moumou et al., 2010; Watson & Zabel, 1982; Castaneda-Acosta et al., 1997). In the crystal structure, molecules are linked into supramolecular chains (Fig. 2) parallel to the c axis by C—H···O hydrogen bonds (Table 1). In addition an intramolecular O—H···N hydrogen bond is also observed.

Related literature top

For background to the medicinal uses of the plant Anvillea radiata, see: El Hassany et al. (2004). For reactivity of this sesquiterpene see: Der-Ren et al. (2006); Neelakantan et al. (2009); Neukirch et al. (2003). For ring puckering parameters, see: Cremer & Pople (1975). For conformations of ten-membered rings, see: Castaneda-Acosta et al. (1997). For related structures, see: Moumou et al. (2010); Watson & Zabel (1982).

Experimental top

The mixture of 6β,7α-epoxy-9α hydoxy partenolide (0.5 g, 2 mmol) and one equivalent of pyrolidine in EtOH (20 ml) was stirred for one night at room temperature. The next day the reaction was stopped by adding water (10 ml) and extracted three times with ethyl acetate (3 x 20 ml). The combined organic layers were dried over anhydrous MgSO₄, filtered and concentrated under vacuum to give 666 mg (1.9 mmol) of solid which was recrystallized in ethyl acetate.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 and SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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).

Figures top

	Fig. 1. Molecular structure of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Packing view showing the C–H···O and O–H···N hydrogen bonds as dashed lines. H atoms not involved in hydrogen bonding have been omitted for clarity.
	Fig. 3. Synthesis of the title compound.

10α-Hydroxy-4,9-dimethyl-13-[(pyrrolidin-1-yl)methyl]-3,8,15- trioxatetracyclo[10.3.0.0^2,4.0^7,9]pentadecan-14-one top

Crystal data top

C₁₉H₂₉NO₅	F(000) = 760
M_r = 351.43	D_x = 1.281 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3417 reflections
a = 8.0714 (2) Å	θ = 2.7–26.4°
b = 10.4571 (3) Å	µ = 0.09 mm⁻¹
c = 21.5816 (8) Å	T = 298 K
V = 1821.56 (10) Å³	Prism, colourless
Z = 4	0.89 × 0.46 × 0.21 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	1660 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.034
Graphite monochromator	θ_max = 26.4°, θ_min = 2.7°
ϕ and ω scans	h = −7→10
8707 measured reflections	k = −13→10
2122 independent reflections	l = −26→25

Refinement top

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.098	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0589P)²] where P = (F_o² + 2F_c²)/3
2122 reflections	(Δ/σ)_max < 0.001
229 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₁₉H₂₉NO₅	V = 1821.56 (10) Å³
M_r = 351.43	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 8.0714 (2) Å	µ = 0.09 mm⁻¹
b = 10.4571 (3) Å	T = 298 K
c = 21.5816 (8) Å	0.89 × 0.46 × 0.21 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	1660 reflections with I > 2σ(I)
8707 measured reflections	R_int = 0.034
2122 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.098	H-atom parameters constrained
S = 1.03	Δρ_max = 0.17 e Å⁻³
2122 reflections	Δρ_min = −0.15 e Å⁻³
229 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.2294 (3)	0.5169 (2)	0.08783 (11)	0.0361 (6)
H1	0.1851	0.5945	0.0685	0.043*
C2	0.3205 (3)	0.5410 (2)	0.14572 (11)	0.0399 (6)
C3	0.3293 (3)	0.6785 (2)	0.16551 (12)	0.0483 (7)
H3A	0.3354	0.6820	0.2104	0.058*
H3B	0.2280	0.7212	0.1530	0.058*
C4	0.4776 (3)	0.7513 (3)	0.13836 (13)	0.0491 (7)
H4A	0.4573	0.8423	0.1424	0.059*
H4B	0.5754	0.7311	0.1626	0.059*
C5	0.5120 (3)	0.7213 (2)	0.07148 (12)	0.0377 (6)
H5	0.4129	0.7113	0.0457	0.045*
C6	0.6598 (3)	0.6526 (2)	0.04855 (11)	0.0361 (5)
C7	0.6555 (3)	0.5740 (2)	−0.01081 (10)	0.0336 (5)
H7	0.7700	0.5517	−0.0214	0.040*
C8	0.5592 (3)	0.4481 (2)	−0.00134 (11)	0.0351 (5)
H8A	0.6027	0.3845	−0.0297	0.042*
H8B	0.5792	0.4177	0.0405	0.042*
C9	0.3708 (3)	0.4590 (2)	−0.01138 (10)	0.0325 (5)
H9	0.3454	0.5497	−0.0179	0.039*
C10	0.2637 (3)	0.4126 (2)	0.04320 (12)	0.0367 (6)
H10	0.3146	0.3389	0.0639	0.044*
C11	0.2981 (3)	0.3852 (2)	−0.06591 (12)	0.0410 (6)
H11	0.3523	0.3016	−0.0685	0.049*
C12	0.1199 (3)	0.3663 (2)	−0.04627 (14)	0.0491 (7)
C13	0.7995 (3)	0.6124 (3)	0.09028 (13)	0.0549 (8)
H13A	0.9032	0.6363	0.0718	0.082*
H13B	0.7963	0.5214	0.0959	0.082*
H13C	0.7881	0.6539	0.1297	0.082*
C14	0.4501 (3)	0.4522 (3)	0.17126 (13)	0.0557 (7)
H14A	0.4431	0.4509	0.2157	0.084*
H14B	0.5580	0.4814	0.1590	0.084*
H14C	0.4321	0.3675	0.1554	0.084*
C15	0.3068 (3)	0.4494 (3)	−0.12859 (12)	0.0469 (6)
H15A	0.2480	0.3971	−0.1585	0.056*
H15B	0.2506	0.5312	−0.1262	0.056*
C16	0.5619 (4)	0.3520 (3)	−0.16867 (15)	0.0686 (9)
H16A	0.4884	0.2950	−0.1910	0.082*
H16B	0.6043	0.3079	−0.1324	0.082*
C17	0.7000 (5)	0.3955 (4)	−0.2091 (2)	0.0935 (13)
H17A	0.7218	0.3332	−0.2414	0.112*
H17B	0.8003	0.4078	−0.1851	0.112*
C18	0.6423 (4)	0.5219 (3)	−0.23718 (14)	0.0664 (9)
H18A	0.7210	0.5895	−0.2283	0.080*
H18B	0.6301	0.5143	−0.2817	0.080*
C19	0.4779 (4)	0.5494 (3)	−0.20714 (12)	0.0553 (7)
H19A	0.4686	0.6394	−0.1968	0.066*
H19B	0.3875	0.5265	−0.2346	0.066*
N	0.4750 (3)	0.47021 (19)	−0.15073 (9)	0.0435 (5)
O1	0.1047 (2)	0.37802 (16)	0.01525 (9)	0.0474 (5)
O2	0.0011 (3)	0.3449 (2)	−0.07852 (11)	0.0696 (6)
O3	0.5907 (2)	0.64734 (16)	−0.06008 (8)	0.0415 (4)
H3	0.5656	0.5999	−0.0888	0.062*
O4	0.6462 (2)	0.78993 (16)	0.04219 (8)	0.0460 (5)
O5	0.1545 (2)	0.48703 (17)	0.14653 (8)	0.0503 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0278 (11)	0.0437 (13)	0.0369 (13)	−0.0005 (11)	0.0061 (10)	0.0094 (10)
C2	0.0353 (13)	0.0507 (14)	0.0338 (13)	−0.0003 (12)	0.0068 (10)	0.0073 (12)
C3	0.0521 (15)	0.0586 (16)	0.0340 (14)	0.0070 (13)	0.0051 (12)	−0.0027 (12)
C4	0.0538 (16)	0.0513 (15)	0.0423 (16)	−0.0036 (13)	0.0025 (13)	−0.0083 (12)
C5	0.0378 (13)	0.0365 (12)	0.0389 (14)	−0.0073 (12)	0.0015 (11)	0.0009 (11)
C6	0.0270 (11)	0.0401 (13)	0.0411 (14)	−0.0065 (11)	−0.0007 (10)	0.0050 (11)
C7	0.0269 (11)	0.0398 (12)	0.0341 (13)	0.0029 (11)	0.0037 (10)	0.0065 (10)
C8	0.0352 (12)	0.0341 (11)	0.0359 (13)	0.0025 (11)	0.0024 (10)	0.0030 (10)
C9	0.0337 (11)	0.0284 (10)	0.0354 (12)	0.0000 (10)	−0.0004 (10)	0.0027 (10)
C10	0.0304 (12)	0.0348 (12)	0.0450 (15)	−0.0028 (10)	−0.0001 (11)	0.0096 (11)
C11	0.0444 (14)	0.0343 (12)	0.0442 (15)	0.0005 (12)	−0.0029 (12)	−0.0032 (11)
C12	0.0517 (17)	0.0366 (13)	0.0591 (19)	−0.0096 (14)	−0.0047 (15)	0.0015 (13)
C13	0.0385 (15)	0.077 (2)	0.0487 (17)	−0.0019 (14)	−0.0071 (13)	0.0033 (14)
C14	0.0566 (16)	0.0671 (17)	0.0434 (16)	0.0044 (16)	−0.0038 (13)	0.0116 (15)
C15	0.0485 (15)	0.0516 (14)	0.0405 (15)	0.0041 (14)	−0.0047 (12)	−0.0067 (12)
C16	0.079 (2)	0.0623 (18)	0.064 (2)	0.0231 (18)	0.0107 (19)	−0.0128 (16)
C17	0.083 (3)	0.116 (3)	0.082 (3)	0.026 (2)	0.027 (2)	−0.008 (2)
C18	0.070 (2)	0.081 (2)	0.0476 (18)	−0.0066 (19)	0.0082 (16)	−0.0081 (16)
C19	0.0636 (17)	0.0695 (18)	0.0327 (14)	0.0029 (17)	−0.0035 (13)	−0.0014 (14)
N	0.0512 (13)	0.0459 (12)	0.0333 (11)	0.0082 (11)	−0.0027 (10)	−0.0041 (9)
O1	0.0366 (10)	0.0480 (10)	0.0576 (12)	−0.0131 (8)	0.0013 (9)	0.0040 (9)
O2	0.0568 (13)	0.0737 (14)	0.0784 (16)	−0.0238 (12)	−0.0205 (12)	−0.0018 (12)
O3	0.0507 (10)	0.0409 (8)	0.0327 (10)	−0.0062 (9)	−0.0004 (8)	0.0074 (7)
O4	0.0488 (10)	0.0406 (9)	0.0485 (11)	−0.0146 (8)	0.0053 (9)	0.0000 (8)
O5	0.0399 (9)	0.0666 (12)	0.0445 (11)	−0.0044 (9)	0.0147 (8)	0.0106 (9)

Geometric parameters (Å, º) top

C1—O5	1.438 (3)	C10—H10	0.9800
C1—C2	1.472 (3)	C11—C15	1.512 (4)
C1—C10	1.481 (3)	C11—C12	1.512 (4)
C1—H1	0.9800	C11—H11	0.9800
C2—O5	1.454 (3)	C12—O2	1.206 (3)
C2—C3	1.501 (4)	C12—O1	1.339 (3)
C2—C14	1.504 (4)	C13—H13A	0.9600
C3—C4	1.535 (4)	C13—H13B	0.9600
C3—H3A	0.9700	C13—H13C	0.9600
C3—H3B	0.9700	C14—H14A	0.9600
C4—C5	1.503 (4)	C14—H14B	0.9600
C4—H4A	0.9700	C14—H14C	0.9600
C4—H4B	0.9700	C15—N	1.455 (3)
C5—O4	1.445 (3)	C15—H15A	0.9700
C5—C6	1.478 (3)	C15—H15B	0.9700
C5—H5	0.9800	C16—N	1.473 (3)
C6—O4	1.446 (3)	C16—C17	1.487 (5)
C6—C13	1.503 (3)	C16—H16A	0.9700
C6—C7	1.523 (3)	C16—H16B	0.9700
C7—O3	1.412 (3)	C17—C18	1.526 (5)
C7—C8	1.543 (3)	C17—H17A	0.9700
C7—H7	0.9800	C17—H17B	0.9700
C8—C9	1.540 (3)	C18—C19	1.504 (4)
C8—H8A	0.9700	C18—H18A	0.9700
C8—H8B	0.9700	C18—H18B	0.9700
C9—C11	1.525 (3)	C19—N	1.473 (3)
C9—C10	1.540 (3)	C19—H19A	0.9700
C9—H9	0.9800	C19—H19B	0.9700
C10—O1	1.464 (3)	O3—H3	0.8200

O5—C1—C2	59.96 (15)	C9—C10—H10	111.2
O5—C1—C10	119.5 (2)	C15—C11—C12	110.7 (2)
C2—C1—C10	125.8 (2)	C15—C11—C9	116.62 (19)
O5—C1—H1	113.7	C12—C11—C9	102.5 (2)
C2—C1—H1	113.7	C15—C11—H11	108.9
C10—C1—H1	113.7	C12—C11—H11	108.9
O5—C2—C1	58.87 (15)	C9—C11—H11	108.9
O5—C2—C3	114.3 (2)	O2—C12—O1	121.1 (3)
C1—C2—C3	115.4 (2)	O2—C12—C11	128.2 (3)
O5—C2—C14	113.4 (2)	O1—C12—C11	110.7 (2)
C1—C2—C14	123.6 (2)	C6—C13—H13A	109.5
C3—C2—C14	117.0 (2)	C6—C13—H13B	109.5
C2—C3—C4	113.8 (2)	H13A—C13—H13B	109.5
C2—C3—H3A	108.8	C6—C13—H13C	109.5
C4—C3—H3A	108.8	H13A—C13—H13C	109.5
C2—C3—H3B	108.8	H13B—C13—H13C	109.5
C4—C3—H3B	108.8	C2—C14—H14A	109.5
H3A—C3—H3B	107.7	C2—C14—H14B	109.5
C5—C4—C3	114.0 (2)	H14A—C14—H14B	109.5
C5—C4—H4A	108.7	C2—C14—H14C	109.5
C3—C4—H4A	108.7	H14A—C14—H14C	109.5
C5—C4—H4B	108.7	H14B—C14—H14C	109.5
C3—C4—H4B	108.7	N—C15—C11	113.8 (2)
H4A—C4—H4B	107.6	N—C15—H15A	108.8
O4—C5—C6	59.31 (14)	C11—C15—H15A	108.8
O4—C5—C4	117.1 (2)	N—C15—H15B	108.8
C6—C5—C4	124.9 (2)	C11—C15—H15B	108.8
O4—C5—H5	114.6	H15A—C15—H15B	107.7
C6—C5—H5	114.6	N—C16—C17	104.8 (3)
C4—C5—H5	114.6	N—C16—H16A	110.8
O4—C6—C5	59.20 (15)	C17—C16—H16A	110.8
O4—C6—C13	113.1 (2)	N—C16—H16B	110.8
C5—C6—C13	122.7 (2)	C17—C16—H16B	110.8
O4—C6—C7	117.0 (2)	H16A—C16—H16B	108.9
C5—C6—C7	121.7 (2)	C16—C17—C18	105.6 (3)
C13—C6—C7	111.7 (2)	C16—C17—H17A	110.6
O3—C7—C6	110.42 (18)	C18—C17—H17A	110.6
O3—C7—C8	112.11 (19)	C16—C17—H17B	110.6
C6—C7—C8	111.14 (18)	C18—C17—H17B	110.6
O3—C7—H7	107.7	H17A—C17—H17B	108.7
C6—C7—H7	107.7	C19—C18—C17	105.3 (3)
C8—C7—H7	107.7	C19—C18—H18A	110.7
C9—C8—C7	114.57 (19)	C17—C18—H18A	110.7
C9—C8—H8A	108.6	C19—C18—H18B	110.7
C7—C8—H8A	108.6	C17—C18—H18B	110.7
C9—C8—H8B	108.6	H18A—C18—H18B	108.8
C7—C8—H8B	108.6	N—C19—C18	105.2 (2)
H8A—C8—H8B	107.6	N—C19—H19A	110.7
C11—C9—C10	102.40 (17)	C18—C19—H19A	110.7
C11—C9—C8	116.8 (2)	N—C19—H19B	110.7
C10—C9—C8	115.03 (19)	C18—C19—H19B	110.7
C11—C9—H9	107.3	H19A—C19—H19B	108.8
C10—C9—H9	107.3	C15—N—C19	111.7 (2)
C8—C9—H9	107.3	C15—N—C16	113.9 (2)
O1—C10—C1	106.59 (19)	C19—N—C16	104.3 (2)
O1—C10—C9	104.76 (18)	C12—O1—C10	110.54 (19)
C1—C10—C9	111.73 (18)	C7—O3—H3	109.5
O1—C10—H10	111.2	C5—O4—C6	61.49 (14)
C1—C10—H10	111.2	C1—O5—C2	61.17 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N	0.82	2.04	2.851 (2)	172
C9—H9···O4ⁱ	0.98	2.38	3.260 (2)	149
C10—H10···O2ⁱⁱ	0.98	2.46	3.392 (3)	158
C19—H19B···O5ⁱⁱⁱ	0.97	2.59	3.357 (3)	136

Symmetry codes: (i) x−1/2, −y+3/2, −z; (ii) x+1/2, −y+1/2, −z; (iii) −x+1/2, −y+1, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₂₉NO₅
M_r	351.43
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	298
a, b, c (Å)	8.0714 (2), 10.4571 (3), 21.5816 (8)
V (Å³)	1821.56 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.89 × 0.46 × 0.21

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8707, 2122, 1660
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.098, 1.03
No. of reflections	2122
No. of parameters	229
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.15

Computer programs: APEX2 (Bruker, 2005), APEX2 and SAINT (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N	0.82	2.04	2.851 (2)	172
C9—H9···O4ⁱ	0.98	2.38	3.260 (2)	149
C10—H10···O2ⁱⁱ	0.98	2.46	3.392 (3)	158
C19—H19B···O5ⁱⁱⁱ	0.97	2.59	3.357 (3)	136

Symmetry codes: (i) x−1/2, −y+3/2, −z; (ii) x+1/2, −y+1/2, −z; (iii) −x+1/2, −y+1, z−1/2.

Acknowledgements

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements.

References

Bruker, (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Volume 67| Part 7| July 2011| Pages o1842-o1843

doi:10.1107/S1600536811024688

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

10α-Hy­dr­oxy-4,9-di­methyl-13-[(pyrrol­idin-1-yl)meth­yl]-3,8,15-trioxa­tetra­cyclo­[10.3.0.02,4.07,9]penta­decan-14-one

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

10α-Hydroxy-4,9-dimethyl-13-[(pyrrolidin-1-yl)methyl]-3,8,15-trioxatetracyclo[10.3.0.0^2,4.0^7,9]pentadecan-14-one