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

Moumou, M.; Benharref, A.; Oudahmane, A.; Elhakmaoui, A.; Berraho, M.

doi:10.1107/S1600536811042012

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 11| November 2011| Pages o2981-o2982

doi:10.1107/S1600536811042012

Open

access

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

Mohamed Moumou,^a Ahmed Benharref,^a Abdelghani Oudahmane,^b Ahmed Elhakmaoui ^c ^* and Moha Berraho ^a

^aLaboratoire de Chimie Biomoléculaire, Substances Naturelles et Réactivité, URAC 16, Faculté des Sciences Semlalia, BP 2390, Bd My Abdellah, 40000 Marrakech, Morocco, ^bUniversite Blaise Pascal, Laboratoire des Mate'riaux Inorganiques, UMR CNRS 6002, 24 Avenue des Landais, 63177 Aubiere, 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 3 October 2011; accepted 11 October 2011; online 22 October 2011)

The title compound, C₂₅H₃₄N₂O₅, 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 contains a fused five- and ten-membered ring system. The ten-membered ring adopts an approximate chair–chair conformation, while the five-membered ring is in an envelope conformation, with the C atom closest to the hydroxy group forming the flap. The piperazine ring is in a chair conformation. In the crystal, O—H⋯O hydrogen bonds connect molecules into chains along [100]. Weak intermolecular C—H⋯O hydrogen bonds are also present.

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 ). For the reactivity of this sesquiterpene, see: Hwang et al. (2006 ); Neukirch et al. (2003 ); Neelakantan et al. (2009 ). For the synthesis, see: Moumou et al. (2010 ). For ring puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₅H₃₄N₂O₅
M_r = 442.54
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.7666 (5) Å
b = 9.6059 (8) Å
c = 31.181 (2) Å
V = 2326.2 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.45 × 0.36 × 0.28 mm

Data collection

Bruker X8 APEX CCD area-detector diffractometer
10922 measured reflections
2723 independent reflections
2362 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.104
S = 1.06
2723 reflections
293 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O2ⁱ	0.82	2.11	2.902 (3)	161
C14—H14B⋯O5ⁱⁱ	0.96	2.59	3.289 (3)	129
C21—H21⋯O1ⁱⁱⁱ	0.93	2.51	3.441 (4)	174
Symmetry codes: (i) x+1, y, z; (ii) x-1, y, z; (iii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXS97 (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/S1600536811042012/lh5350sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811042012/lh5350Isup2.hkl

checkCIF report

Comment top

The natural sesquiterpene lactone, 9α - hydroxypartenolide is the main constituent of the chloroform extract of the aerial parts of Anvillea radiata (El Hassany et al., 2004) and of Anvillea garcini (Abdel Sattar et al., (1996). The reactivity of this sesquiterpene lactone and its derivatives has been the subject of several studies (Neukirch et al., 2003; Hwang et al., 2006; Neelakantan et al., 2009), in order to prepare products of value which can be used in the pharmacological industry. In this context, we have synthesed from 9α-hydroxyparthenolide the 6β,7α- epoxy-9apha hydoxy partenolide (9α-hydroxy-4,8-dimethyl-12- methylen-3,14-dioxa-tricyclo[9.3.0.0²,⁴]tetradec-7-en-13-one) (Moumou et al., 2010) and then prepared the title compound (I). The crystal structure of (I) is determined herein. The molecule contains a fused ring system and phenylpiperazine group as a substituent to a lactone ring. The molecular structure, Fig.1, shows that the lactone ring adopts an envelope conformation, as indicated by the Cremer & Pople (1975) puckering parameters Q = 0.347 (2)Å and ϕ = 75.6 (3)°. The ten-membered ring displays an approximate chair-chair conformation, while the piperazine ring has a perfect chair conformation with QT = 0.570 (2) Å, θ = 180.0 (2)° and ϕ2 = 150 (10)°. In the crystal structure, molecules are connected through O—H···O hydrogen bonds (Fig.2), forming chains along [100].

Related literature top

For background to the medicinal uses of the plant Anvillea radiata, see: Abdel Sattar et al. (1996); Bellakhdar (1997); El Hassany et al. (2004); For reactivity of this sesquiterpene, see: Hwang et al. (2006). Neukirch et al. (2003); Neelakantan et al. (2009) For the synthesis, see: Moumou et al. (2010). For ring puckering parameters, see: Cremer & Pople (1975).

Experimental top

A mixture of 6β,7α-epoxy-9α-hydoxypartenolide (9α-hydroxy-4,8-dimethyl-12- methylen-3,14-dioxa-tricyclo[9.3.0.02,4]tetradec-7-en-13-one) (0.5 g, 2 mmol) and one equivalent of 1-phenylpiperazine in EtOH (20 ml) was stirred for twelve hours at room temperature. Then 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 895 mg (1.8 mmol) of the title compound, which was recrystallized in ethyl acetate.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXS97 (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 displacement ellipsoids drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Packing view showing O–H···O hydrogen bonds as dashed lines. H atoms not involved in hydrogen bonding have been omitted for clarity.

10αHydroxy-4,9-dimethyl-13-[(4-phenylpiperazin-1-yl)methyl]- 3,8,15-trioxatetracyclo[10.3.0.0^2,4.0^7,9]tetradecan-14-one top

Crystal data top

C₂₅H₃₄N₂O₅	F(000) = 952
M_r = 442.54	D_x = 1.264 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 10922 reflections
a = 7.7666 (5) Å	θ = 2.7–26.4°
b = 9.6059 (8) Å	µ = 0.09 mm⁻¹
c = 31.181 (2) Å	T = 298 K
V = 2326.2 (3) Å³	Prism, colourless
Z = 4	0.45 × 0.36 × 0.28 mm

Data collection top

Bruker X8 APEX CCD area-detector diffractometer	2362 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.024
Graphite monochromator	θ_max = 26.4°, θ_min = 2.7°
ϕ and ω scans	h = −9→9
10922 measured reflections	k = −11→7
2723 independent reflections	l = −38→34

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0537P)² + 0.4378P] where P = (F_o² + 2F_c²)/3
2723 reflections	(Δ/σ)_max < 0.001
293 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₅H₃₄N₂O₅	V = 2326.2 (3) Å³
M_r = 442.54	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.7666 (5) Å	µ = 0.09 mm⁻¹
b = 9.6059 (8) Å	T = 298 K
c = 31.181 (2) Å	0.45 × 0.36 × 0.28 mm

Data collection top

Bruker X8 APEX CCD area-detector diffractometer	2362 reflections with I > 2σ(I)
10922 measured reflections	R_int = 0.024
2723 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.104	H-atom parameters constrained
S = 1.06	Δρ_max = 0.17 e Å⁻³
2723 reflections	Δρ_min = −0.18 e Å⁻³
293 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	0.5441 (3)	0.2316 (2)	0.91768 (7)	0.0347 (5)
H1	0.4879	0.1665	0.8979	0.042*
C2	0.5370 (3)	0.1777 (2)	0.96267 (7)	0.0327 (5)
H2	0.6143	0.2252	0.9827	0.039*
C3	0.4930 (3)	0.0341 (3)	0.97477 (7)	0.0349 (5)
C4	0.5705 (3)	−0.0184 (3)	1.01607 (8)	0.0415 (6)
H4A	0.4920	−0.0840	1.0293	0.050*
H4B	0.5859	0.0591	1.0356	0.050*
C5	0.7438 (3)	−0.0892 (3)	1.00857 (8)	0.0435 (6)
H5A	0.7981	−0.1076	1.0360	0.052*
H5B	0.7252	−0.1777	0.9943	0.052*
C6	0.8616 (3)	−0.0009 (3)	0.98170 (8)	0.0383 (6)
H6	0.8588	0.0985	0.9888	0.046*
C7	0.9154 (3)	−0.0312 (3)	0.93753 (8)	0.0383 (6)
C8	0.9740 (3)	0.0848 (3)	0.90772 (8)	0.0404 (6)
H8	1.0567	0.0437	0.8876	0.048*
C9	0.8307 (4)	0.1514 (3)	0.88067 (8)	0.0416 (6)
H9A	0.7518	0.0783	0.8720	0.050*
H9B	0.8825	0.1885	0.8548	0.050*
C10	0.7253 (3)	0.2680 (2)	0.90184 (7)	0.0311 (5)
H10	0.7914	0.3042	0.9262	0.037*
C11	0.5317 (3)	0.4573 (3)	0.89329 (8)	0.0414 (6)
C12	0.6839 (3)	0.3904 (3)	0.87154 (7)	0.0376 (6)
H12	0.6455	0.3523	0.8440	0.045*
C13	0.8251 (4)	0.4953 (3)	0.86298 (8)	0.0431 (6)
H13A	0.7729	0.5793	0.8516	0.052*
H13B	0.8786	0.5194	0.8901	0.052*
C14	0.4374 (4)	−0.0747 (3)	0.94329 (9)	0.0473 (6)
H14A	0.3988	−0.0306	0.9174	0.071*
H14B	0.3451	−0.1284	0.9554	0.071*
H14C	0.5328	−0.1349	0.9369	0.071*
C15	1.1040 (4)	0.5453 (3)	0.83687 (8)	0.0519 (7)
H15A	1.1452	0.5467	0.8662	0.062*
H15B	1.0668	0.6387	0.8295	0.062*
C16	0.9013 (3)	0.4473 (3)	0.78904 (8)	0.0490 (7)
H16A	0.8618	0.5393	0.7808	0.059*
H16B	0.8051	0.3836	0.7864	0.059*
C17	1.0437 (4)	0.4021 (3)	0.75924 (8)	0.0509 (7)
H17A	1.0794	0.3082	0.7664	0.061*
H17B	1.0018	0.4018	0.7299	0.061*
C18	1.2483 (4)	0.5027 (4)	0.80761 (8)	0.0542 (8)
H18A	1.3418	0.5691	0.8100	0.065*
H18B	1.2915	0.4122	0.8163	0.065*
C19	1.3260 (4)	0.4797 (3)	0.73301 (8)	0.0448 (6)
C20	1.3357 (4)	0.3688 (3)	0.70444 (8)	0.0473 (6)
H20	1.2490	0.3020	0.7040	0.057*
C21	1.4749 (4)	0.3575 (4)	0.67644 (8)	0.0571 (8)
H21	1.4797	0.2835	0.6573	0.069*
C22	1.6044 (4)	0.4538 (4)	0.67685 (9)	0.0645 (9)
H22	1.6992	0.4434	0.6589	0.077*
C23	1.5932 (4)	0.5657 (4)	0.70384 (10)	0.0714 (10)
H23	1.6792	0.6331	0.7035	0.086*
C24	1.4562 (4)	0.5797 (4)	0.73158 (9)	0.0615 (8)
H24	1.4503	0.6568	0.7496	0.074*
C26	0.8708 (4)	−0.1630 (3)	0.91409 (9)	0.0535 (7)
H26A	0.8222	−0.2288	0.9338	0.080*
H26B	0.9730	−0.2015	0.9015	0.080*
H26C	0.7886	−0.1428	0.8919	0.080*
N1	0.9589 (3)	0.4506 (2)	0.83356 (6)	0.0398 (5)
N2	1.1901 (3)	0.4959 (2)	0.76275 (6)	0.0461 (6)
O1	0.4819 (3)	0.5750 (2)	0.89055 (6)	0.0565 (5)
O2	0.3686 (2)	0.14622 (18)	0.97984 (5)	0.0400 (4)
O3	0.4524 (2)	0.36458 (19)	0.91853 (5)	0.0447 (4)
O5	1.0321 (2)	−0.0547 (2)	0.97319 (6)	0.0543 (5)
O4	1.0600 (2)	0.19268 (19)	0.92937 (7)	0.0538 (5)
H4	1.1392	0.1600	0.9436	0.081*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0319 (12)	0.0320 (12)	0.0403 (12)	−0.0020 (11)	−0.0021 (11)	0.0019 (10)
C2	0.0281 (11)	0.0336 (12)	0.0364 (11)	−0.0008 (11)	0.0030 (10)	0.0008 (9)
C3	0.0274 (11)	0.0351 (12)	0.0421 (12)	−0.0020 (10)	0.0068 (10)	0.0002 (10)
C4	0.0464 (14)	0.0380 (13)	0.0402 (12)	−0.0040 (12)	0.0048 (11)	0.0072 (11)
C5	0.0486 (14)	0.0374 (14)	0.0446 (13)	0.0030 (12)	−0.0051 (12)	0.0065 (11)
C6	0.0304 (12)	0.0343 (13)	0.0502 (13)	0.0040 (11)	−0.0070 (11)	−0.0018 (11)
C7	0.0330 (12)	0.0338 (13)	0.0479 (13)	0.0062 (11)	−0.0035 (11)	−0.0007 (11)
C8	0.0326 (12)	0.0363 (13)	0.0522 (14)	0.0066 (11)	0.0058 (11)	−0.0029 (11)
C9	0.0485 (15)	0.0362 (13)	0.0401 (12)	0.0049 (13)	0.0062 (12)	0.0012 (11)
C10	0.0303 (12)	0.0302 (12)	0.0328 (11)	−0.0005 (10)	−0.0014 (9)	0.0020 (9)
C11	0.0404 (13)	0.0420 (14)	0.0417 (13)	0.0051 (13)	−0.0057 (11)	0.0079 (11)
C12	0.0414 (13)	0.0336 (13)	0.0377 (12)	0.0019 (11)	−0.0008 (11)	0.0024 (10)
C13	0.0503 (14)	0.0352 (13)	0.0438 (13)	−0.0031 (13)	0.0073 (12)	0.0012 (11)
C14	0.0444 (14)	0.0394 (15)	0.0582 (15)	−0.0041 (13)	0.0002 (13)	−0.0033 (12)
C15	0.0527 (16)	0.0597 (18)	0.0434 (13)	−0.0120 (16)	0.0041 (12)	−0.0116 (13)
C16	0.0419 (14)	0.0639 (18)	0.0413 (13)	−0.0058 (15)	−0.0014 (11)	0.0009 (13)
C17	0.0485 (15)	0.0646 (18)	0.0396 (13)	−0.0098 (16)	−0.0015 (12)	−0.0086 (13)
C18	0.0467 (14)	0.073 (2)	0.0431 (13)	−0.0101 (15)	0.0003 (12)	−0.0112 (15)
C19	0.0479 (14)	0.0498 (15)	0.0368 (12)	−0.0031 (14)	0.0010 (11)	0.0005 (12)
C20	0.0538 (16)	0.0476 (15)	0.0403 (13)	−0.0030 (15)	0.0013 (13)	0.0019 (12)
C21	0.069 (2)	0.0614 (18)	0.0413 (14)	0.0143 (19)	0.0050 (14)	0.0000 (14)
C22	0.0538 (18)	0.098 (3)	0.0419 (15)	0.003 (2)	0.0075 (13)	0.0051 (17)
C23	0.0574 (19)	0.099 (3)	0.0578 (18)	−0.030 (2)	0.0051 (16)	0.0013 (19)
C24	0.0633 (18)	0.068 (2)	0.0528 (16)	−0.0199 (19)	0.0080 (15)	−0.0106 (15)
C26	0.0663 (19)	0.0335 (14)	0.0608 (16)	0.0041 (14)	0.0044 (15)	−0.0079 (13)
N1	0.0409 (11)	0.0424 (12)	0.0362 (10)	−0.0028 (11)	0.0019 (9)	−0.0001 (9)
N2	0.0454 (12)	0.0543 (14)	0.0386 (10)	−0.0091 (12)	0.0029 (10)	−0.0090 (10)
O1	0.0590 (12)	0.0477 (11)	0.0627 (11)	0.0188 (11)	0.0078 (10)	0.0146 (9)
O2	0.0310 (8)	0.0414 (9)	0.0477 (9)	0.0018 (8)	0.0081 (7)	0.0000 (8)
O3	0.0333 (9)	0.0458 (10)	0.0548 (10)	0.0089 (9)	0.0045 (8)	0.0136 (9)
O5	0.0371 (10)	0.0594 (12)	0.0662 (12)	0.0123 (10)	−0.0069 (9)	0.0060 (10)
O4	0.0350 (10)	0.0429 (11)	0.0834 (14)	−0.0036 (9)	−0.0090 (10)	0.0003 (10)

Geometric parameters (Å, º) top

C1—O3	1.463 (3)	C13—H13A	0.9700
C1—C2	1.496 (3)	C13—H13B	0.9700
C1—C10	1.532 (3)	C14—H14A	0.9600
C1—H1	0.9800	C14—H14B	0.9600
C2—O2	1.445 (3)	C14—H14C	0.9600
C2—C3	1.471 (3)	C15—N1	1.452 (3)
C2—H2	0.9800	C15—C18	1.502 (4)
C3—O2	1.456 (3)	C15—H15A	0.9700
C3—C14	1.497 (4)	C15—H15B	0.9700
C3—C4	1.508 (3)	C16—N1	1.459 (3)
C4—C5	1.526 (4)	C16—C17	1.508 (4)
C4—H4A	0.9700	C16—H16A	0.9700
C4—H4B	0.9700	C16—H16B	0.9700
C5—C6	1.503 (4)	C17—N2	1.455 (3)
C5—H5A	0.9700	C17—H17A	0.9700
C5—H5B	0.9700	C17—H17B	0.9700
C6—O5	1.446 (3)	C18—N2	1.471 (3)
C6—C7	1.468 (3)	C18—H18A	0.9700
C6—H6	0.9800	C18—H18B	0.9700
C7—O5	1.452 (3)	C19—C20	1.390 (4)
C7—C26	1.502 (4)	C19—C24	1.395 (4)
C7—C8	1.521 (4)	C19—N2	1.414 (3)
C8—O4	1.406 (3)	C20—C21	1.394 (4)
C8—C9	1.536 (3)	C20—H20	0.9300
C8—H8	0.9800	C21—C22	1.367 (5)
C9—C10	1.537 (3)	C21—H21	0.9300
C9—H9A	0.9700	C22—C23	1.368 (5)
C9—H9B	0.9700	C22—H22	0.9300
C10—C12	1.542 (3)	C23—C24	1.378 (4)
C10—H10	0.9800	C23—H23	0.9300
C11—O1	1.198 (3)	C24—H24	0.9300
C11—O3	1.339 (3)	C26—H26A	0.9600
C11—C12	1.507 (3)	C26—H26B	0.9600
C12—C13	1.513 (4)	C26—H26C	0.9600
C12—H12	0.9800	O4—H4	0.8200
C13—N1	1.451 (3)

O3—C1—C2	105.50 (18)	N1—C13—H13A	108.4
O3—C1—C10	104.70 (18)	C12—C13—H13A	108.4
C2—C1—C10	114.50 (19)	N1—C13—H13B	108.4
O3—C1—H1	110.6	C12—C13—H13B	108.4
C2—C1—H1	110.6	H13A—C13—H13B	107.4
C10—C1—H1	110.6	C3—C14—H14A	109.5
O2—C2—C3	59.88 (14)	C3—C14—H14B	109.5
O2—C2—C1	116.93 (19)	H14A—C14—H14B	109.5
C3—C2—C1	125.0 (2)	C3—C14—H14C	109.5
O2—C2—H2	114.5	H14A—C14—H14C	109.5
C3—C2—H2	114.5	H14B—C14—H14C	109.5
C1—C2—H2	114.5	N1—C15—C18	111.4 (2)
O2—C3—C2	59.19 (15)	N1—C15—H15A	109.3
O2—C3—C14	113.4 (2)	C18—C15—H15A	109.3
C2—C3—C14	123.6 (2)	N1—C15—H15B	109.3
O2—C3—C4	114.79 (19)	C18—C15—H15B	109.3
C2—C3—C4	116.1 (2)	H15A—C15—H15B	108.0
C14—C3—C4	116.2 (2)	N1—C16—C17	111.6 (2)
C3—C4—C5	111.7 (2)	N1—C16—H16A	109.3
C3—C4—H4A	109.3	C17—C16—H16A	109.3
C5—C4—H4A	109.3	N1—C16—H16B	109.3
C3—C4—H4B	109.3	C17—C16—H16B	109.3
C5—C4—H4B	109.3	H16A—C16—H16B	108.0
H4A—C4—H4B	107.9	N2—C17—C16	110.4 (2)
C6—C5—C4	111.8 (2)	N2—C17—H17A	109.6
C6—C5—H5A	109.3	C16—C17—H17A	109.6
C4—C5—H5A	109.3	N2—C17—H17B	109.6
C6—C5—H5B	109.3	C16—C17—H17B	109.6
C4—C5—H5B	109.3	H17A—C17—H17B	108.1
H5A—C5—H5B	107.9	N2—C18—C15	111.1 (2)
O5—C6—C7	59.77 (15)	N2—C18—H18A	109.4
O5—C6—C5	117.3 (2)	C15—C18—H18A	109.4
C7—C6—C5	125.7 (2)	N2—C18—H18B	109.4
O5—C6—H6	114.2	C15—C18—H18B	109.4
C7—C6—H6	114.2	H18A—C18—H18B	108.0
C5—C6—H6	114.2	C20—C19—C24	117.9 (3)
O5—C7—C6	59.36 (15)	C20—C19—N2	123.0 (2)
O5—C7—C26	112.7 (2)	C24—C19—N2	119.1 (2)
C6—C7—C26	123.9 (2)	C19—C20—C21	120.2 (3)
O5—C7—C8	113.3 (2)	C19—C20—H20	119.9
C6—C7—C8	120.8 (2)	C21—C20—H20	119.9
C26—C7—C8	112.9 (2)	C22—C21—C20	120.8 (3)
O4—C8—C7	112.9 (2)	C22—C21—H21	119.6
O4—C8—C9	107.5 (2)	C20—C21—H21	119.6
C7—C8—C9	115.1 (2)	C21—C22—C23	119.4 (3)
O4—C8—H8	107.0	C21—C22—H22	120.3
C7—C8—H8	107.0	C23—C22—H22	120.3
C9—C8—H8	107.0	C22—C23—C24	120.8 (3)
C8—C9—C10	117.0 (2)	C22—C23—H23	119.6
C8—C9—H9A	108.0	C24—C23—H23	119.6
C10—C9—H9A	108.0	C23—C24—C19	120.8 (3)
C8—C9—H9B	108.0	C23—C24—H24	119.6
C10—C9—H9B	108.0	C19—C24—H24	119.6
H9A—C9—H9B	107.3	C7—C26—H26A	109.5
C1—C10—C9	117.5 (2)	C7—C26—H26B	109.5
C1—C10—C12	100.36 (18)	H26A—C26—H26B	109.5
C9—C10—C12	113.83 (19)	C7—C26—H26C	109.5
C1—C10—H10	108.2	H26A—C26—H26C	109.5
C9—C10—H10	108.2	H26B—C26—H26C	109.5
C12—C10—H10	108.2	C13—N1—C15	108.97 (19)
O1—C11—O3	121.5 (2)	C13—N1—C16	112.8 (2)
O1—C11—C12	128.6 (2)	C15—N1—C16	108.6 (2)
O3—C11—C12	109.9 (2)	C19—N2—C17	117.8 (2)
C11—C12—C13	111.3 (2)	C19—N2—C18	113.5 (2)
C11—C12—C10	102.31 (19)	C17—N2—C18	109.8 (2)
C13—C12—C10	117.7 (2)	C2—O2—C3	60.93 (15)
C11—C12—H12	108.4	C11—O3—C1	110.30 (18)
C13—C12—H12	108.4	C6—O5—C7	60.87 (15)
C10—C12—H12	108.4	C8—O4—H4	109.5
N1—C13—C12	115.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O2ⁱ	0.82	2.11	2.902 (3)	161
C14—H14B···O5ⁱⁱ	0.96	2.59	3.289 (3)	129
C21—H21···O1ⁱⁱⁱ	0.93	2.51	3.441 (4)	174

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

Experimental details

Crystal data
Chemical formula	C₂₅H₃₄N₂O₅
M_r	442.54
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	298
a, b, c (Å)	7.7666 (5), 9.6059 (8), 31.181 (2)
V (Å³)	2326.2 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.45 × 0.36 × 0.28

Data collection
Diffractometer	Bruker X8 APEX CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	10922, 2723, 2362
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.104, 1.06
No. of reflections	2723
No. of parameters	293
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.18

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (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
O4—H4···O2ⁱ	0.82	2.11	2.902 (3)	161
C14—H14B···O5ⁱⁱ	0.96	2.59	3.289 (3)	129
C21—H21···O1ⁱⁱⁱ	0.93	2.51	3.441 (4)	174

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

Acknowledgements

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for financial support.

References

Abdel Sattar, E., Galal, A. M. & Mossa, J. S. (1996). J. Nat. Prod. 59, 403–405. CrossRef CAS PubMed Google Scholar
Bellakhdar, J. (1997). La Pharmacopé Marocaine Traditionnelle, pp. 272–274. Paris: Edition Ibis Press. Google Scholar
Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
El Hassany, B., El Hanbali, F., Akssira, M., Mellouki, F., Haidou, A. & Barero, A. F. (2004). Fitoterapia, 75, 573–576. Web of Science CrossRef PubMed CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Hwang, D.-R., Wu, Y.-S., Chang, C.-W., Lien, T.-W., Chen, W.-C., Tan, U.-K., Hsu, J. T. A. & Hsieh, H.-P. (2006). Bioorg. Med. Chem. 14, 83—91. Google Scholar
Moumou, M., Akssira, M., El Ammari, L., Benharref, A. & Berraho, M. (2010). Acta Cryst. E66, o2395. Web of Science CSD CrossRef IUCr Journals Google Scholar
Neelakantan, S., Nasim, Sh., Guzman, M. L., Jordan, C. T. & Crooks, P. A. (2009). Bioorg. Med. Chem. Lett. 19, 4346–4349. Web of Science CrossRef PubMed CAS Google Scholar
Neukirch, H., Kaneider, N. C., Wiedermann, C. J., Guerriero, A. & D'Ambrosio, M. (2003). Bioorg. Med. Chem. 11, 1503–1510. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 11| November 2011| Pages o2981-o2982

doi:10.1107/S1600536811042012

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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