10α-Hy­droxy-13-{[4-(2-hy­droxy­phen­yl)piperazin-1-yl]meth­yl}-4,9-dimethyl-3,8,15-trioxatetra­cyclo­[10.3.0.02,4.07,9]penta­decan-14-one

Moumou, M.; Benharref, A.; El Ammari, L.; Adil, M.; Berraho, M.

doi:10.1107/S1600536812013876

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Pages o1309-o1310

doi:10.1107/S1600536812013876

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

Mohamed Moumou,^a Ahmed Benharref,^b Lahcen El Ammari,^c Mina Adil ^a ^* and Moha Berraho ^b

^aLaboratoire de Chimie Bioorganique et Analytique, URAC 22, BP 146, FSTM, Université Hassan II, Mohammedia–Casablanca 20810 Mohammedia, Morocco, ^bLaboratoire de Chimie Biomoléculaire, Substances Naturelles et Réactivité, URAC 16, Faculté des Sciences Semlalia, BP 2390, Bd My Abdellah, 40000 Marrakech, Morocco, and ^cLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Avenue Ibn Battouta, BP 1014 Rabat, Morocco
^*Correspondence e-mail: mberraho@yahoo.fr

(Received 28 March 2012; accepted 30 March 2012; online 6 April 2012)

The title compound, C₂₅H₃₄N₂O₆, 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 ten-membered ring adopts an approximate chair–chair conformation, while the piperazine ring displays a near regular chair conformation and the five-membered ring an envelope conformation with the C atom closest to the hydroxy group forming the flap. The molecular conformation is stabilized by an O—H⋯N hydrogen bond, which generates an S(7) loop, and the crystal structure features weak C—H⋯O interactions.

Related literature

For background to the medicinal uses of the plant Anvillea adiata, see: Abdel Sattar et al. (1996 ); El Hassany et al. (2004 ); Qureshi et al.(1990 ). For the reactivity of this sesquiterpene, see: Hwang et al. (2006 ); Neukirch et al. (2003 ); Neelakantan et al. (2009 ). For ring puckering parameters, see: Cremer & Pople (1975 ). For the synthesis, see: Moumou et al. (2010 ).

Experimental

Crystal data

C₂₅H₃₄N₂O₆
M_r = 458.54
Orthorhombic, P 2₁ 2₁ 2₁
a = 8.0978 (2) Å
b = 10.3660 (3) Å
c = 28.8194 (8) Å
V = 2419.15 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 180 K
0.27 × 0.21 × 0.06 mm

Data collection

Agilent Xcalibur Sapphire1 long-nozzle diffractometer
27441 measured reflections
2829 independent reflections
2540 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.093
S = 1.05
2829 reflections
302 parameters
H-atom parameters constrained
Δρ_max = 0.19 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
O5—H5⋯N1	0.82	2.15	2.952 (2)	164
C1—H1⋯O4ⁱ	0.98	2.49	3.440 (3)	165
C10—H10⋯O1ⁱⁱ	0.98	2.36	3.232 (2)	148
C18—H18A⋯O6	0.97	2.32	2.943 (3)	121
C25—H25⋯O2ⁱⁱⁱ	0.93	2.55	3.299 (4)	138
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{5\over 2}}, -z]$ ; (iii) $[-x+{\script{3\over 2}}, -y+2, z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2010 ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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/S1600536812013876/bt5864sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812013876/bt5864Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812013876/bt5864Isup3.cml

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 have been the subject of several studies Neukirch et al., 2003; Hwang et al., 2006; Neelakantan et al., 2009), in order to prepare products with high value which can be used in the pharmacological industry. In this context, we have synthesed, from 9α-hydroxyparthenolide, the 6β,7α-epoxy-9α- hydoxypartenolide (9α-hydroxy-4,8-dimethyl-12-methylen-3,14-dioxa-tetracyclo [9.3.0.0²,⁴]tetradec-7-en-13-one)(Moumou et al., 2010). This Epoxy-hydroxypartenolide treated with one equivalent of 1-(2-hydroxyphenyl- piperazine) gives the title compound(I)with a yield of 93%. The crystal structure of (I) is reported herein.The molecule contains a fused ring system and hydroxyphenylpiperazine group as a substituent to a lactone ring. The molecular structure of (I), Fig.1, shows the lactone ring to adopt an envelope conformation, as indicated by Cremer & Pople (1975) puckering parameters Q = 0.306 (2) Å and ϕ =79.5 (4)°. The ten-membered ring displays an approximate chair-chair conformation, while the piperazine ring has a perfect chair conformation with QT = 0.582 (3) Å, θ = 180.0 (2)° and ϕ2 =319 (24)°. In the crystal, C—H···O hydrogen bonding links the molecules into sheets lying parallel to the bc plane (Table 1, Fig.2). 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 adiata, see: Abdel Sattar et al. (1996); El Hassany et al. (2004); Qureshi et al.(1990). For the reactivity of this sesquiterpene, see: Hwang et al. (2006); Neukirch et al. (2003); Neelakantan et al. (2009). For ring puckering parameters, see: Cremer & Pople (1975). For the synthesis, see: Moumou et al. (2010).

Experimental top

The mixture of 6β,7α-epoxy-9α-hydoxypartenolide(9α-hydroxy- 4,8-dimethyl-12-methylen-3,14-tricyclo [9.3.0.0₂,₄]tetradec-7-en-13-one) (5 g, 3.57 mmol) and one equivalent of 1-(2-Hydroxyphenyl-piperazine) in EtOH (30 ml)was stirred for twelve hours at room temperature. Then the reaction was stopped by adding water (20 ml) and extracted three times with ethyl acetate (3 x 30 ml). The combined organic layers were dried over anhydrous MgSO₄, filtered and concentrated under vacuum to give 1.5 g (3.32 mmol) of the title compound, which was recrystalized in ethyl acetate.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); 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 displacement ellipsoids drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. : Partial packing view showing the C–H···O hydrogen bonds as dashed lines. H atoms not involved in hydrogen bonding have been omitted for clarity.

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

Crystal data top

C₂₅H₃₄N₂O₆	F(000) = 984
M_r = 458.54	D_x = 1.259 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4934 reflections
a = 8.0978 (2) Å	θ = 2.4–26.4°
b = 10.3660 (3) Å	µ = 0.09 mm⁻¹
c = 28.8194 (8) Å	T = 180 K
V = 2419.15 (11) Å³	Platelet, colourless
Z = 4	0.27 × 0.21 × 0.06 mm

Data collection top

Agilent Xcalibur Sapphire1 long-nozzle diffractometer	2540 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.034
Graphite monochromator	θ_max = 26.4°, θ_min = 2.4°
Detector resolution: 8.2632 pixels mm^-1	h = −10→10
ω scan	k = −12→12
27441 measured reflections	l = −35→36
2829 independent reflections

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.093	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0508P)² + 0.396P] where P = (F_o² + 2F_c²)/3
2829 reflections	(Δ/σ)_max = 0.002
302 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₅H₃₄N₂O₆	V = 2419.15 (11) Å³
M_r = 458.54	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 8.0978 (2) Å	µ = 0.09 mm⁻¹
b = 10.3660 (3) Å	T = 180 K
c = 28.8194 (8) Å	0.27 × 0.21 × 0.06 mm

Data collection top

Agilent Xcalibur Sapphire1 long-nozzle diffractometer	2540 reflections with I > 2σ(I)
27441 measured reflections	R_int = 0.034
2829 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.093	H-atom parameters constrained
S = 1.05	Δρ_max = 0.19 e Å⁻³
2829 reflections	Δρ_min = −0.18 e Å⁻³
302 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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
C1	0.9344 (2)	0.90928 (19)	−0.02860 (7)	0.0367 (4)
H1	0.8850	0.8325	−0.0428	0.044*
C2	0.9628 (2)	1.01210 (18)	−0.06365 (7)	0.0365 (4)
H2	1.0098	1.0913	−0.0506	0.044*
C3	0.8665 (2)	1.0334 (2)	−0.10613 (7)	0.0396 (4)
C4	0.8570 (3)	1.1717 (2)	−0.12197 (7)	0.0445 (5)
H4A	0.8464	1.1734	−0.1555	0.053*
H4B	0.9593	1.2150	−0.1139	0.053*
C5	0.7118 (3)	1.2463 (2)	−0.10047 (8)	0.0462 (5)
H5A	0.7327	1.3380	−0.1037	0.055*
H5B	0.6123	1.2265	−0.1178	0.055*
C6	0.6825 (2)	1.21618 (18)	−0.05000 (7)	0.0379 (4)
H6	0.7828	1.2067	−0.0313	0.045*
C7	0.5359 (2)	1.1463 (2)	−0.03197 (7)	0.0396 (4)
C8	0.5440 (2)	1.06794 (19)	0.01276 (7)	0.0394 (4)
H8	0.4306	1.0443	0.0211	0.047*
C9	0.6417 (2)	0.94191 (19)	0.00614 (7)	0.0372 (4)
H9A	0.6198	0.9086	−0.0247	0.045*
H9B	0.6022	0.8787	0.0283	0.045*
C10	0.8304 (2)	0.95749 (18)	0.01223 (7)	0.0335 (4)
H10	0.8530	1.0498	0.0158	0.040*
C11	1.0873 (3)	0.8737 (2)	0.03774 (8)	0.0446 (5)
C12	0.9101 (3)	0.8883 (2)	0.05318 (7)	0.0412 (5)
H12	0.8608	0.8024	0.0561	0.049*
C13	0.9013 (3)	0.9554 (3)	0.10023 (7)	0.0496 (5)
H13A	0.9726	0.9101	0.1218	0.060*
H13B	0.9435	1.0425	0.0970	0.060*
C14	0.7331 (3)	0.9440 (2)	−0.12263 (8)	0.0483 (5)
H14A	0.7379	0.9369	−0.1558	0.073*
H14B	0.6273	0.9775	−0.1136	0.073*
H14C	0.7486	0.8604	−0.1090	0.073*
C15	0.3946 (3)	1.1047 (3)	−0.06229 (9)	0.0563 (6)
H15A	0.2926	1.1346	−0.0492	0.084*
H15B	0.3928	1.0123	−0.0643	0.084*
H15C	0.4082	1.1407	−0.0927	0.084*
C16	0.6773 (3)	0.8326 (2)	0.13338 (8)	0.0527 (6)
H16A	0.7548	0.7954	0.1553	0.063*
H16B	0.6741	0.7773	0.1062	0.063*
C17	0.5082 (3)	0.8371 (2)	0.15515 (8)	0.0536 (6)
H17A	0.4288	0.8697	0.1328	0.064*
H17B	0.4746	0.7508	0.1641	0.064*
C18	0.5649 (4)	1.0502 (2)	0.18283 (8)	0.0589 (6)
H18A	0.5678	1.1051	0.2101	0.071*
H18B	0.4873	1.0870	0.1609	0.071*
C19	0.7342 (4)	1.0444 (2)	0.16120 (8)	0.0562 (6)
H19A	0.7689	1.1308	0.1526	0.067*
H19B	0.8125	1.0112	0.1837	0.067*
C20	0.3698 (3)	0.9137 (3)	0.22451 (7)	0.0543 (6)
C21	0.2250 (4)	0.8504 (4)	0.21250 (9)	0.0761 (9)
H21	0.2159	0.8136	0.1832	0.091*
C22	0.3734 (4)	0.9667 (3)	0.26908 (8)	0.0709 (8)
C23	0.0932 (4)	0.8409 (5)	0.24322 (11)	0.0987 (13)
H23	−0.0019	0.7968	0.2345	0.118*
C24	0.1028 (5)	0.8958 (5)	0.28612 (11)	0.1027 (14)
H24	0.0137	0.8906	0.3064	0.123*
C25	0.2443 (5)	0.9589 (4)	0.29923 (10)	0.0941 (12)
H25	0.2519	0.9960	0.3285	0.113*
N1	0.7348 (2)	0.96134 (17)	0.11978 (6)	0.0455 (4)
N2	0.5106 (3)	0.92072 (19)	0.19603 (6)	0.0495 (5)
O1	0.5493 (2)	1.28526 (14)	−0.02754 (5)	0.0491 (4)
O2	1.03111 (18)	0.97758 (15)	−0.10802 (5)	0.0469 (4)
O3	1.09685 (17)	0.88006 (14)	−0.00863 (5)	0.0451 (4)
O4	1.2079 (2)	0.85660 (19)	0.06106 (7)	0.0647 (5)
O5	0.6083 (2)	1.14333 (15)	0.04947 (5)	0.0477 (4)
H5	0.6267	1.0969	0.0719	0.071*
O6	0.5154 (3)	1.0222 (2)	0.28351 (6)	0.0802 (7)
H6A	0.5209	1.0960	0.2733	0.120*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0321 (9)	0.0299 (9)	0.0479 (11)	0.0032 (8)	−0.0011 (8)	−0.0058 (8)
C2	0.0312 (9)	0.0324 (9)	0.0459 (11)	0.0008 (8)	0.0036 (8)	−0.0072 (8)
C3	0.0390 (10)	0.0366 (10)	0.0432 (10)	0.0039 (9)	0.0050 (9)	−0.0047 (9)
C4	0.0502 (12)	0.0408 (11)	0.0424 (11)	−0.0014 (10)	0.0038 (10)	0.0026 (9)
C5	0.0512 (12)	0.0354 (10)	0.0520 (12)	0.0050 (10)	−0.0030 (10)	0.0036 (9)
C6	0.0368 (9)	0.0273 (9)	0.0495 (11)	0.0038 (8)	−0.0024 (9)	−0.0031 (8)
C7	0.0292 (9)	0.0368 (10)	0.0528 (11)	0.0055 (8)	0.0020 (9)	−0.0069 (9)
C8	0.0286 (9)	0.0387 (11)	0.0510 (11)	−0.0012 (8)	0.0058 (9)	−0.0084 (9)
C9	0.0334 (9)	0.0302 (9)	0.0481 (11)	−0.0046 (8)	0.0032 (8)	−0.0024 (9)
C10	0.0338 (9)	0.0247 (8)	0.0422 (10)	−0.0027 (8)	0.0003 (8)	−0.0024 (8)
C11	0.0449 (11)	0.0295 (10)	0.0595 (14)	0.0035 (9)	−0.0052 (10)	0.0031 (9)
C12	0.0423 (11)	0.0317 (10)	0.0497 (12)	−0.0038 (9)	−0.0032 (9)	0.0042 (9)
C13	0.0526 (12)	0.0487 (12)	0.0476 (12)	−0.0130 (11)	−0.0063 (10)	0.0030 (10)
C14	0.0514 (12)	0.0449 (12)	0.0486 (12)	0.0008 (11)	−0.0045 (10)	−0.0093 (10)
C15	0.0347 (10)	0.0661 (15)	0.0681 (15)	0.0008 (11)	−0.0093 (11)	−0.0049 (13)
C16	0.0673 (15)	0.0400 (11)	0.0507 (13)	−0.0082 (11)	0.0034 (11)	−0.0016 (10)
C17	0.0652 (15)	0.0479 (12)	0.0477 (12)	−0.0124 (12)	0.0016 (11)	−0.0064 (10)
C18	0.0862 (18)	0.0468 (13)	0.0437 (12)	−0.0020 (14)	0.0024 (12)	−0.0055 (10)
C19	0.0812 (17)	0.0421 (12)	0.0453 (12)	−0.0141 (13)	−0.0024 (12)	−0.0038 (10)
C20	0.0631 (14)	0.0615 (15)	0.0383 (11)	0.0001 (12)	−0.0038 (10)	0.0010 (10)
C21	0.0652 (17)	0.109 (2)	0.0540 (15)	−0.0100 (18)	0.0020 (13)	−0.0159 (16)
C22	0.0793 (18)	0.093 (2)	0.0400 (12)	−0.0080 (18)	−0.0029 (13)	−0.0030 (14)
C23	0.0665 (18)	0.152 (4)	0.077 (2)	−0.017 (2)	0.0028 (16)	−0.017 (2)
C24	0.080 (2)	0.166 (4)	0.0622 (18)	−0.005 (3)	0.0191 (17)	−0.009 (2)
C25	0.099 (2)	0.136 (3)	0.0474 (15)	−0.010 (3)	0.0122 (16)	−0.0135 (19)
N1	0.0591 (11)	0.0380 (9)	0.0395 (9)	−0.0088 (9)	−0.0025 (8)	−0.0001 (8)
N2	0.0633 (12)	0.0474 (10)	0.0377 (9)	−0.0045 (9)	−0.0025 (9)	−0.0010 (8)
O1	0.0493 (8)	0.0347 (7)	0.0632 (9)	0.0146 (7)	0.0045 (8)	−0.0050 (7)
O2	0.0422 (8)	0.0502 (9)	0.0483 (8)	0.0074 (7)	0.0107 (7)	−0.0054 (7)
O3	0.0345 (7)	0.0412 (8)	0.0595 (9)	0.0091 (6)	0.0002 (7)	0.0014 (7)
O4	0.0506 (10)	0.0639 (11)	0.0795 (12)	0.0140 (9)	−0.0195 (9)	0.0087 (10)
O5	0.0556 (9)	0.0409 (8)	0.0464 (8)	0.0056 (7)	0.0029 (7)	−0.0096 (7)
O6	0.0937 (15)	0.1145 (18)	0.0323 (8)	−0.0403 (14)	−0.0040 (9)	−0.0159 (10)

Geometric parameters (Å, º) top

C1—O3	1.468 (2)	C13—H13A	0.9700
C1—C2	1.486 (3)	C13—H13B	0.9700
C1—C10	1.531 (3)	C14—H14A	0.9600
C1—H1	0.9800	C14—H14B	0.9600
C2—O2	1.438 (2)	C14—H14C	0.9600
C2—C3	1.468 (3)	C15—H15A	0.9600
C2—H2	0.9800	C15—H15B	0.9600
C3—O2	1.454 (2)	C15—H15C	0.9600
C3—C14	1.501 (3)	C16—N1	1.467 (3)
C3—C4	1.507 (3)	C16—C17	1.507 (4)
C4—C5	1.538 (3)	C16—H16A	0.9700
C4—H4A	0.9700	C16—H16B	0.9700
C4—H4B	0.9700	C17—N2	1.463 (3)
C5—C6	1.507 (3)	C17—H17A	0.9700
C5—H5A	0.9700	C17—H17B	0.9700
C5—H5B	0.9700	C18—N2	1.462 (3)
C6—O1	1.447 (2)	C18—C19	1.507 (4)
C6—C7	1.484 (3)	C18—H18A	0.9700
C6—H6	0.9800	C18—H18B	0.9700
C7—O1	1.450 (3)	C19—N1	1.472 (3)
C7—C15	1.503 (3)	C19—H19A	0.9700
C7—C8	1.525 (3)	C19—H19B	0.9700
C8—O5	1.415 (2)	C20—C21	1.387 (4)
C8—C9	1.539 (3)	C20—C22	1.397 (3)
C8—H8	0.9800	C20—N2	1.407 (3)
C9—C10	1.546 (3)	C21—C23	1.390 (4)
C9—H9A	0.9700	C21—H21	0.9300
C9—H9B	0.9700	C22—O6	1.352 (4)
C10—C12	1.524 (3)	C22—C25	1.362 (4)
C10—H10	0.9800	C23—C24	1.363 (5)
C11—O4	1.198 (3)	C23—H23	0.9300
C11—O3	1.340 (3)	C24—C25	1.372 (5)
C11—C12	1.510 (3)	C24—H24	0.9300
C12—C13	1.525 (3)	C25—H25	0.9300
C12—H12	0.9800	O5—H5	0.8200
C13—N1	1.463 (3)	O6—H6A	0.8200

O3—C1—C2	106.00 (15)	N1—C13—H13A	108.8
O3—C1—C10	105.01 (15)	C12—C13—H13A	108.8
C2—C1—C10	111.93 (16)	N1—C13—H13B	108.8
O3—C1—H1	111.2	C12—C13—H13B	108.8
C2—C1—H1	111.2	H13A—C13—H13B	107.7
C10—C1—H1	111.2	C3—C14—H14A	109.5
O2—C2—C3	60.01 (12)	C3—C14—H14B	109.5
O2—C2—C1	119.04 (16)	H14A—C14—H14B	109.5
C3—C2—C1	126.31 (18)	C3—C14—H14C	109.5
O2—C2—H2	113.6	H14A—C14—H14C	109.5
C3—C2—H2	113.6	H14B—C14—H14C	109.5
C1—C2—H2	113.6	C7—C15—H15A	109.5
O2—C3—C2	58.99 (12)	C7—C15—H15B	109.5
O2—C3—C14	113.75 (17)	H15A—C15—H15B	109.5
C2—C3—C14	123.63 (19)	C7—C15—H15C	109.5
O2—C3—C4	114.47 (17)	H15A—C15—H15C	109.5
C2—C3—C4	115.01 (18)	H15B—C15—H15C	109.5
C14—C3—C4	117.03 (19)	N1—C16—C17	111.8 (2)
C3—C4—C5	113.32 (18)	N1—C16—H16A	109.3
C3—C4—H4A	108.9	C17—C16—H16A	109.3
C5—C4—H4A	108.9	N1—C16—H16B	109.3
C3—C4—H4B	108.9	C17—C16—H16B	109.3
C5—C4—H4B	108.9	H16A—C16—H16B	107.9
H4A—C4—H4B	107.7	N2—C17—C16	110.0 (2)
C6—C5—C4	113.91 (18)	N2—C17—H17A	109.7
C6—C5—H5A	108.8	C16—C17—H17A	109.7
C4—C5—H5A	108.8	N2—C17—H17B	109.7
C6—C5—H5B	108.8	C16—C17—H17B	109.7
C4—C5—H5B	108.8	H17A—C17—H17B	108.2
H5A—C5—H5B	107.7	N2—C18—C19	110.2 (2)
O1—C6—C7	59.28 (12)	N2—C18—H18A	109.6
O1—C6—C5	116.54 (17)	C19—C18—H18A	109.6
C7—C6—C5	124.42 (19)	N2—C18—H18B	109.6
O1—C6—H6	114.9	C19—C18—H18B	109.6
C7—C6—H6	114.9	H18A—C18—H18B	108.1
C5—C6—H6	114.9	N1—C19—C18	111.2 (2)
O1—C7—C6	59.10 (13)	N1—C19—H19A	109.4
O1—C7—C15	113.14 (19)	C18—C19—H19A	109.4
C6—C7—C15	123.0 (2)	N1—C19—H19B	109.4
O1—C7—C8	116.85 (17)	C18—C19—H19B	109.4
C6—C7—C8	121.45 (17)	H19A—C19—H19B	108.0
C15—C7—C8	111.79 (19)	C21—C20—C22	115.7 (3)
O5—C8—C7	110.71 (17)	C21—C20—N2	124.3 (2)
O5—C8—C9	111.84 (17)	C22—C20—N2	119.9 (3)
C7—C8—C9	111.69 (16)	C20—C21—C23	121.6 (3)
O5—C8—H8	107.5	C20—C21—H21	119.2
C7—C8—H8	107.5	C23—C21—H21	119.2
C9—C8—H8	107.5	O6—C22—C25	118.8 (3)
C8—C9—C10	113.91 (16)	O6—C22—C20	117.9 (3)
C8—C9—H9A	108.8	C25—C22—C20	123.1 (3)
C10—C9—H9A	108.8	C24—C23—C21	120.3 (3)
C8—C9—H9B	108.8	C24—C23—H23	119.9
C10—C9—H9B	108.8	C21—C23—H23	119.9
H9A—C9—H9B	107.7	C23—C24—C25	119.7 (3)
C12—C10—C1	102.06 (15)	C23—C24—H24	120.1
C12—C10—C9	117.19 (17)	C25—C24—H24	120.1
C1—C10—C9	114.97 (16)	C22—C25—C24	119.6 (3)
C12—C10—H10	107.3	C22—C25—H25	120.2
C1—C10—H10	107.3	C24—C25—H25	120.2
C9—C10—H10	107.3	C13—N1—C16	110.91 (19)
O4—C11—O3	121.3 (2)	C13—N1—C19	109.86 (18)
O4—C11—C12	128.6 (2)	C16—N1—C19	108.35 (16)
O3—C11—C12	110.09 (18)	C20—N2—C18	116.3 (2)
C11—C12—C10	102.80 (17)	C20—N2—C17	115.4 (2)
C11—C12—C13	110.61 (18)	C18—N2—C17	109.78 (17)
C10—C12—C13	117.03 (17)	C6—O1—C7	61.63 (12)
C11—C12—H12	108.7	C2—O2—C3	61.00 (13)
C10—C12—H12	108.7	C11—O3—C1	110.46 (16)
C13—C12—H12	108.7	C8—O5—H5	109.5
N1—C13—C12	113.86 (18)	C22—O6—H6A	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···N1	0.82	2.15	2.952 (2)	164
C1—H1···O4ⁱ	0.98	2.49	3.440 (3)	165
C10—H10···O1ⁱⁱ	0.98	2.36	3.232 (2)	148
C18—H18A···O6	0.97	2.32	2.943 (3)	121
C25—H25···O2ⁱⁱⁱ	0.93	2.55	3.299 (4)	138

Symmetry codes: (i) x−1/2, −y+3/2, −z; (ii) x+1/2, −y+5/2, −z; (iii) −x+3/2, −y+2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₅H₃₄N₂O₆
M_r	458.54
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	180
a, b, c (Å)	8.0978 (2), 10.3660 (3), 28.8194 (8)
V (Å³)	2419.15 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.27 × 0.21 × 0.06

Data collection
Diffractometer	Agilent Xcalibur Sapphire1 long-nozzle diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	27441, 2829, 2540
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.093, 1.05
No. of reflections	2829
No. of parameters	302
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.18

Computer programs: CrysAlis PRO (Agilent, 2010), 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
O5—H5···N1	0.82	2.15	2.952 (2)	164
C1—H1···O4ⁱ	0.98	2.49	3.440 (3)	165
C10—H10···O1ⁱⁱ	0.98	2.36	3.232 (2)	148
C18—H18A···O6	0.97	2.32	2.943 (3)	121
C25—H25···O2ⁱⁱⁱ	0.93	2.55	3.299 (4)	138

Symmetry codes: (i) x−1/2, −y+3/2, −z; (ii) x+1/2, −y+5/2, −z; (iii) −x+3/2, −y+2, z+1/2.

Acknowledgements

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

References

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Volume 68| Part 5| May 2012| Pages o1309-o1310

doi:10.1107/S1600536812013876

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

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