9α-Hy­droxy-12-{[4-(4-meth­oxy­phen­yl)piperazin-1-yl]meth­yl}-4,8-dimethyl-3,14-dioxatricyclo­[9.3.0.02,4]tetra­dec-7-en-13-one

Moumou, M.; Benharref, A.; Daran, J.-C.; Mellouki, F.; Berraho, M.

doi:10.1107/S1600536812003662

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 3| March 2012| Pages o589-o590

doi:10.1107/S1600536812003662

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access

9α-Hydroxy-12-{[4-(4-methoxyphenyl)piperazin-1-yl]methyl}-4,8-dimethyl-3,14-dioxatricyclo[9.3.0.0^2,4]tetradec-7-en-13-one

Mohamed Moumou,^a Ahmed Benharref,^a Jean-Claude Daran,^b Fouad Mellouki ^c ^* and Moha Berraho ^a

^aLaboratoire de Chimie Biomoléculaire, Substances Naturelles et Réactivité, URAC 16, Faculté des Sciences Semlalia, BP 2390, Boulevard My Abdellah, 40000 Marrakech, Morocco, ^bLaboratoire de Chimie de Coordination, 205 route de Narbonne, 31077 Toulouse Cedex 04, 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 17 January 2012; accepted 27 January 2012; online 4 February 2012)

The title compound, C₂₆H₃₆N₂O₅, 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), wich was isolated from the chloroform extract of the aerial parts of Anvillea radiata. The molecule is built up from fused five- and ten-membered rings with the methoxyphenylpiperazine group as a substituent. The ten-membered ring adopts an approximate chair–chair conformation, while the piperazine ring displays a chair conformation and the five-membered ring a flattened envelope conformation; the C(H)—C—C(H) atoms representing the flap lie out of the mean plane through the remaining four atoms by 0.343 (3) Å. The dihedral angle between the mean planes of the ten-membered ring and the lactone ring is 18.12 (14)°. An intramolecular O—H⋯N hydrogen bond occurs. The crystal structure features weak C—H⋯O interactions.

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 ring-puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₆H₃₆N₂O₅
M_r = 456.57
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.7066 (7) Å
b = 11.9033 (11) Å
c = 30.322 (4) Å
V = 2420.6 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 180 K
0.33 × 0.17 × 0.04 mm

Data collection

Agilent Xcalibur Sapphire1 (long nozzle) diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.732, T_max = 1.000
14543 measured reflections
4925 independent reflections
3663 reflections with I > 2σ(I)
R_int = 0.055

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.130
S = 1.04
4925 reflections
303 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯N1	0.84	2.14	2.977 (4)	170
C2—H2⋯O12ⁱ	1.00	2.42	3.225 (4)	137
C5—H5B⋯O3ⁱⁱ	0.99	2.45	3.310 (4)	145
C7—H7⋯O14ⁱⁱⁱ	0.95	2.50	3.198 (4)	130
C15—H15A⋯O12ⁱ	0.99	2.57	3.413 (4)	143
C15—H15A⋯O14ⁱ	0.99	2.50	3.469 (4)	165
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-1, y, z.

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/S1600536812003662/ds2172sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812003662/ds2172Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812003662/ds2172Isup3.cml

checkCIF report

Comment top

Our work lies within the framework of the valorization of medicinals plants and concerning the Anvillea radiata wich is a plant that grows in northern Africa and particularly found in the two Maghreb countries, Morocco and Algeria. This plant is used in traditional local medicine for the treatment of dysentery, gastric-intestinal disorders (Bellakhdar, 1997), hypoglycemic activity (Qureshi et al., 1990), and has been reported to have antitumoral activity (Abdel Sattar et al., 1996). In our study of different Moroccan endemic plants, we have demonstrated that the aerial parts of Anvillea radiata could be used as a renewable source of 9-hydroxyparthenolide (El Hassany et al., 2004). In order to prepare products with high added value that can be used in pharmacology and cosmetics industry, we studied the chemical reactivity of this major constituent of Anvillea radiata. Thus, treatment of this sesquiterpene lactone by an equivalent amount of 1-(4-methoxyphenylpiperazine) in ethanol led to the title compound with a yield of 78%. The crystal structure of (I) is reported herein. The molecule contains a fused ring system and methoxyphenylpiperazine 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 = 0.216 (3) Å and ϕ = 69.7 (8)°. The atom C11 deviate from the mean plane through other four atoms in the ring by 0.343 (2) Å. The ten-membered ring displays an approximate chair–chair conformation, while the piperazine ring has a perfect chair conformation with QT = 0.557 (3) Å, θ = 3.4 (3)° and ϕ2 = 33 (6)°. In the crystal structure, the molecules are linked by C—H···O intermolecular hydrogen bonds into chains along the b axis (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 radiata, see: Abdel Sattar et al. (1996); Bellakhdar (1997); El Hassany et al. (2004); Qureshi et al. (1990). For ring-puckering parameters, see: Cremer & Pople (1975).

Experimental top

The mixture of 9α-hydroxyparthenolide (1 g, (3.78 mmol) and one equivalent of 1-(4-methoxyphenylpipirazine) in EtOH (30 ml) was stirred for one night at room temperature. The next day the reaction was stopped by adding water (20 ml) and extracted three times with ethyl acetate (3 × 30 ml). The combined organic layers were dried over anhydrous MgSO₄, filtered and concentrated under vacuum to give 1.34 g (2.94 mmol) of the title compound, which was recrystallized 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.

9α-Hydroxy-12-{[4-(4-methoxyphenyl)piperazin-1-yl]methyl}-4,8-dimethyl- 3,14-dioxatricyclo[9.3.0.0^2,4]tetradec-7-en-13-one top

Crystal data top

C₂₆H₃₆N₂O₅	F(000) = 984
M_r = 456.57	D_x = 1.253 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 14543 reflections
a = 6.7066 (7) Å	θ = 3.1–26.4°
b = 11.9033 (11) Å	µ = 0.09 mm⁻¹
c = 30.322 (4) Å	T = 180 K
V = 2420.6 (4) Å³	Platelet, colourless
Z = 4	0.33 × 0.17 × 0.04 mm

Data collection top

Agilent Xcalibur Sapphire1 (long nozzle) diffractometer	4925 independent reflections
Radiation source: fine-focus sealed tube	3663 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.055
Detector resolution: 8.2632 pixels mm^-1	θ_max = 26.4°, θ_min = 3.1°
ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −14→14
T_min = 0.732, T_max = 1.000	l = −37→37
14543 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.055	H-atom parameters constrained
wR(F²) = 0.130	w = 1/[σ²(F_o²) + (0.0567P)²] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
4925 reflections	Δρ_max = 0.25 e Å⁻³
303 parameters	Δρ_min = −0.23 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0073 (12)

Crystal data top

C₂₆H₃₆N₂O₅	V = 2420.6 (4) Å³
M_r = 456.57	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 6.7066 (7) Å	µ = 0.09 mm⁻¹
b = 11.9033 (11) Å	T = 180 K
c = 30.322 (4) Å	0.33 × 0.17 × 0.04 mm

Data collection top

Agilent Xcalibur Sapphire1 (long nozzle) diffractometer	4925 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	3663 reflections with I > 2σ(I)
T_min = 0.732, T_max = 1.000	R_int = 0.055
14543 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.130	H-atom parameters constrained
S = 1.04	Δρ_max = 0.25 e Å⁻³
4925 reflections	Δρ_min = −0.23 e Å⁻³
303 parameters

Special details top

Experimental. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. CrysAlisPro (Agilent Technologies)

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	0.4429 (4)	0.9320 (2)	0.06430 (8)	0.0236 (6)
H1	0.5156	0.9747	0.0877	0.028*
C2	0.3207 (4)	1.0088 (2)	0.03673 (9)	0.0276 (6)
H2	0.2198	0.9692	0.0181	0.033*
C4	0.2646 (4)	1.1235 (2)	0.04810 (10)	0.0328 (7)
C5	0.0642 (5)	1.1608 (2)	0.03175 (11)	0.0440 (8)
H5A	0.0334	1.1215	0.0038	0.053*
H5B	0.0681	1.2425	0.0256	0.053*
C6	−0.1006 (5)	1.1365 (3)	0.06533 (12)	0.0500 (9)
H6A	−0.0928	1.1917	0.0897	0.060*
H6B	−0.2323	1.1447	0.0510	0.060*
C7	−0.0803 (4)	1.0198 (2)	0.08363 (11)	0.0377 (7)
H7	−0.1012	0.9598	0.0635	0.045*
C8	−0.0368 (5)	0.9912 (3)	0.12466 (10)	0.0396 (8)
C9	0.0201 (4)	0.8728 (3)	0.13688 (10)	0.0382 (7)
H9	−0.0145	0.8614	0.1686	0.046*
C10	0.2457 (4)	0.8572 (2)	0.13205 (9)	0.0306 (6)
H10A	0.2871	0.7920	0.1502	0.037*
H10B	0.3133	0.9245	0.1440	0.037*
C11	0.3171 (4)	0.8384 (2)	0.08456 (8)	0.0227 (6)
H11	0.1959	0.8291	0.0657	0.027*
C12	0.4457 (4)	0.7345 (2)	0.07835 (8)	0.0243 (6)
H12	0.5218	0.7194	0.1061	0.029*
C13	0.5872 (4)	0.7650 (2)	0.04265 (9)	0.0266 (6)
C15	0.3307 (4)	0.6301 (2)	0.06537 (9)	0.0288 (6)
H15A	0.2635	0.6437	0.0368	0.035*
H15B	0.4256	0.5673	0.0612	0.035*
C16	0.2748 (4)	0.5460 (2)	0.13653 (9)	0.0309 (7)
H16A	0.3659	0.6011	0.1504	0.037*
H16B	0.3552	0.4806	0.1271	0.037*
C17	0.1246 (4)	0.5089 (3)	0.16934 (9)	0.0358 (7)
H17A	0.1933	0.4746	0.1949	0.043*
H17B	0.0488	0.5749	0.1800	0.043*
C18	−0.1058 (4)	0.4730 (2)	0.11077 (9)	0.0327 (7)
H18A	−0.1952	0.5357	0.1190	0.039*
H18B	−0.1878	0.4138	0.0967	0.039*
C19	0.0472 (4)	0.5141 (2)	0.07857 (9)	0.0328 (7)
H19A	0.1264	0.4495	0.0678	0.039*
H19B	−0.0213	0.5480	0.0529	0.039*
C20	−0.1351 (4)	0.3686 (2)	0.18020 (9)	0.0271 (6)
C21	−0.0596 (5)	0.3360 (2)	0.22117 (9)	0.0383 (7)
H21	0.0699	0.3598	0.2297	0.046*
C22	−0.1693 (5)	0.2703 (3)	0.24923 (10)	0.0429 (8)
H22	−0.1147	0.2493	0.2769	0.051*
C23	−0.3549 (5)	0.2348 (3)	0.23802 (10)	0.0413 (8)
C24	−0.4336 (5)	0.2676 (3)	0.19821 (11)	0.0467 (8)
H24	−0.5644	0.2447	0.1902	0.056*
C25	−0.3234 (4)	0.3338 (3)	0.16971 (10)	0.0387 (7)
H25	−0.3798	0.3555	0.1423	0.046*
C26	0.3438 (5)	1.1828 (3)	0.08780 (12)	0.0526 (10)
H26A	0.4715	1.1494	0.0964	0.079*
H26B	0.2485	1.1756	0.1121	0.079*
H26C	0.3634	1.2625	0.0809	0.079*
C27	−0.0231 (7)	1.0695 (3)	0.16314 (13)	0.0744 (13)
H27A	−0.0360	1.1472	0.1528	0.112*
H27B	0.1062	1.0598	0.1777	0.112*
H27C	−0.1304	1.0527	0.1841	0.112*
C28	−0.6231 (7)	0.1128 (6)	0.2554 (2)	0.134 (3)
H28A	−0.7310	0.1678	0.2527	0.201*
H28B	−0.6591	0.0564	0.2776	0.201*
H28C	−0.6019	0.0758	0.2269	0.201*
N1	0.1814 (3)	0.59719 (17)	0.09797 (7)	0.0254 (5)
N2	−0.0123 (3)	0.42794 (18)	0.15021 (7)	0.0286 (5)
O3	0.4135 (3)	1.10270 (15)	0.01501 (7)	0.0388 (5)
O4	−0.0873 (3)	0.79295 (17)	0.11206 (8)	0.0440 (6)
H4	−0.0112	0.7400	0.1049	0.066*
O5	−0.4482 (4)	0.1672 (2)	0.26829 (8)	0.0655 (8)
O12	0.6957 (3)	0.70592 (16)	0.02200 (7)	0.0392 (5)
O14	0.5817 (3)	0.87658 (14)	0.03489 (6)	0.0277 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0273 (14)	0.0170 (13)	0.0264 (13)	0.0045 (11)	0.0020 (12)	−0.0043 (11)
C2	0.0301 (14)	0.0167 (12)	0.0360 (15)	−0.0029 (12)	−0.0034 (13)	0.0024 (13)
C4	0.0362 (15)	0.0138 (13)	0.0484 (18)	0.0002 (12)	−0.0031 (14)	−0.0001 (13)
C5	0.0467 (18)	0.0231 (15)	0.062 (2)	0.0085 (14)	−0.0062 (17)	0.0091 (15)
C6	0.0412 (18)	0.0364 (18)	0.072 (2)	0.0170 (16)	−0.0093 (18)	0.0051 (18)
C7	0.0255 (14)	0.0313 (16)	0.056 (2)	0.0021 (14)	−0.0035 (15)	−0.0011 (15)
C8	0.0371 (17)	0.0342 (17)	0.0476 (19)	0.0160 (15)	0.0053 (15)	−0.0058 (15)
C9	0.0415 (17)	0.0354 (16)	0.0377 (16)	0.0084 (14)	0.0085 (15)	−0.0036 (15)
C10	0.0373 (15)	0.0254 (15)	0.0292 (15)	0.0072 (13)	0.0056 (13)	0.0000 (13)
C11	0.0273 (13)	0.0154 (12)	0.0254 (13)	0.0033 (11)	−0.0001 (11)	−0.0005 (11)
C12	0.0321 (14)	0.0164 (13)	0.0243 (13)	0.0055 (11)	0.0037 (12)	−0.0002 (11)
C13	0.0318 (14)	0.0178 (13)	0.0301 (15)	0.0059 (12)	0.0005 (13)	−0.0005 (12)
C15	0.0411 (15)	0.0178 (13)	0.0275 (14)	0.0053 (13)	0.0049 (13)	0.0000 (12)
C16	0.0339 (16)	0.0270 (15)	0.0319 (15)	−0.0020 (12)	−0.0040 (13)	0.0092 (13)
C17	0.0423 (17)	0.0355 (16)	0.0294 (15)	−0.0113 (14)	−0.0069 (14)	0.0075 (13)
C18	0.0419 (17)	0.0257 (14)	0.0304 (15)	−0.0056 (13)	−0.0096 (14)	0.0057 (12)
C19	0.0479 (17)	0.0237 (14)	0.0269 (14)	−0.0051 (14)	−0.0052 (14)	0.0025 (12)
C20	0.0375 (15)	0.0154 (12)	0.0283 (14)	0.0028 (11)	−0.0006 (12)	−0.0014 (11)
C21	0.0473 (18)	0.0352 (17)	0.0325 (15)	−0.0144 (15)	−0.0045 (15)	0.0053 (14)
C22	0.059 (2)	0.0404 (18)	0.0295 (15)	−0.0120 (17)	−0.0055 (16)	0.0058 (15)
C23	0.0438 (18)	0.0407 (18)	0.0395 (18)	−0.0049 (15)	0.0043 (15)	0.0094 (15)
C24	0.0338 (16)	0.048 (2)	0.058 (2)	−0.0046 (16)	−0.0044 (16)	0.0198 (17)
C25	0.0367 (16)	0.0369 (17)	0.0425 (17)	0.0059 (15)	−0.0034 (14)	0.0138 (15)
C26	0.056 (2)	0.0249 (16)	0.077 (3)	0.0041 (16)	−0.0127 (19)	−0.0184 (17)
C27	0.103 (3)	0.056 (2)	0.064 (2)	0.039 (2)	−0.001 (2)	−0.022 (2)
C28	0.076 (3)	0.183 (6)	0.143 (5)	−0.071 (4)	−0.035 (3)	0.119 (5)
N1	0.0358 (13)	0.0180 (11)	0.0223 (11)	−0.0021 (10)	−0.0044 (10)	0.0038 (9)
N2	0.0372 (13)	0.0231 (11)	0.0255 (12)	−0.0044 (10)	−0.0039 (11)	0.0039 (10)
O3	0.0443 (11)	0.0162 (9)	0.0558 (13)	−0.0018 (9)	0.0035 (11)	0.0104 (9)
O4	0.0342 (12)	0.0337 (12)	0.0640 (14)	−0.0016 (10)	0.0071 (11)	0.0012 (11)
O5	0.0575 (15)	0.0798 (19)	0.0593 (15)	−0.0293 (15)	−0.0015 (13)	0.0339 (15)
O12	0.0498 (13)	0.0286 (10)	0.0390 (12)	0.0102 (10)	0.0163 (10)	−0.0017 (9)
O14	0.0314 (10)	0.0177 (9)	0.0341 (10)	0.0027 (8)	0.0081 (9)	0.0003 (8)

Geometric parameters (Å, º) top

C1—O14	1.448 (3)	C16—C17	1.483 (4)
C1—C2	1.485 (4)	C16—H16A	0.9900
C1—C11	1.526 (3)	C16—H16B	0.9900
C1—H1	1.0000	C17—N2	1.452 (3)
C2—O3	1.439 (3)	C17—H17A	0.9900
C2—C4	1.457 (4)	C17—H17B	0.9900
C2—H2	1.0000	C18—N2	1.453 (3)
C4—O3	1.437 (4)	C18—C19	1.499 (4)
C4—C26	1.494 (4)	C18—H18A	0.9900
C4—C5	1.500 (4)	C18—H18B	0.9900
C5—C6	1.530 (4)	C19—N1	1.460 (3)
C5—H5A	0.9900	C19—H19A	0.9900
C5—H5B	0.9900	C19—H19B	0.9900
C6—C7	1.502 (4)	C20—C25	1.367 (4)
C6—H6A	0.9900	C20—C21	1.396 (4)
C6—H6B	0.9900	C20—N2	1.416 (3)
C7—C8	1.323 (4)	C21—C22	1.370 (4)
C7—H7	0.9500	C21—H21	0.9500
C8—C27	1.496 (5)	C22—C23	1.358 (4)
C8—C9	1.507 (4)	C22—H22	0.9500
C9—O4	1.410 (4)	C23—O5	1.371 (4)
C9—C10	1.532 (4)	C23—C24	1.374 (4)
C9—H9	1.0000	C24—C25	1.384 (4)
C10—C11	1.534 (4)	C24—H24	0.9500
C10—H10A	0.9900	C25—H25	0.9500
C10—H10B	0.9900	C26—H26A	0.9800
C11—C12	1.520 (3)	C26—H26B	0.9800
C11—H11	1.0000	C26—H26C	0.9800
C12—C13	1.484 (4)	C27—H27A	0.9800
C12—C15	1.515 (4)	C27—H27B	0.9800
C12—H12	1.0000	C27—H27C	0.9800
C13—O12	1.190 (3)	C28—O5	1.396 (5)
C13—O14	1.350 (3)	C28—H28A	0.9800
C15—N1	1.460 (3)	C28—H28B	0.9800
C15—H15A	0.9900	C28—H28C	0.9800
C15—H15B	0.9900	O4—H4	0.8400
C16—N1	1.460 (3)

O14—C1—C2	106.8 (2)	N1—C16—H16A	109.3
O14—C1—C11	105.74 (18)	C17—C16—H16A	109.3
C2—C1—C11	111.8 (2)	N1—C16—H16B	109.3
O14—C1—H1	110.8	C17—C16—H16B	109.3
C2—C1—H1	110.8	H16A—C16—H16B	107.9
C11—C1—H1	110.8	N2—C17—C16	111.0 (2)
O3—C2—C4	59.49 (17)	N2—C17—H17A	109.4
O3—C2—C1	119.8 (2)	C16—C17—H17A	109.4
C4—C2—C1	125.9 (2)	N2—C17—H17B	109.4
O3—C2—H2	113.6	C16—C17—H17B	109.4
C4—C2—H2	113.6	H17A—C17—H17B	108.0
C1—C2—H2	113.6	N2—C18—C19	111.2 (2)
O3—C4—C2	59.63 (17)	N2—C18—H18A	109.4
O3—C4—C26	113.4 (3)	C19—C18—H18A	109.4
C2—C4—C26	122.8 (3)	N2—C18—H18B	109.4
O3—C4—C5	116.3 (2)	C19—C18—H18B	109.4
C2—C4—C5	115.5 (3)	H18A—C18—H18B	108.0
C26—C4—C5	116.4 (3)	N1—C19—C18	112.4 (2)
C4—C5—C6	111.8 (3)	N1—C19—H19A	109.1
C4—C5—H5A	109.3	C18—C19—H19A	109.1
C6—C5—H5A	109.3	N1—C19—H19B	109.1
C4—C5—H5B	109.3	C18—C19—H19B	109.1
C6—C5—H5B	109.3	H19A—C19—H19B	107.9
H5A—C5—H5B	107.9	C25—C20—C21	117.2 (3)
C7—C6—C5	110.8 (3)	C25—C20—N2	122.6 (2)
C7—C6—H6A	109.5	C21—C20—N2	119.9 (2)
C5—C6—H6A	109.5	C22—C21—C20	121.1 (3)
C7—C6—H6B	109.5	C22—C21—H21	119.5
C5—C6—H6B	109.5	C20—C21—H21	119.5
H6A—C6—H6B	108.1	C23—C22—C21	121.0 (3)
C8—C7—C6	127.2 (3)	C23—C22—H22	119.5
C8—C7—H7	116.4	C21—C22—H22	119.5
C6—C7—H7	116.4	C22—C23—O5	115.7 (3)
C7—C8—C27	126.0 (3)	C22—C23—C24	118.9 (3)
C7—C8—C9	121.9 (3)	O5—C23—C24	125.4 (3)
C27—C8—C9	112.0 (3)	C23—C24—C25	120.3 (3)
O4—C9—C8	111.7 (3)	C23—C24—H24	119.8
O4—C9—C10	111.8 (2)	C25—C24—H24	119.8
C8—C9—C10	109.9 (3)	C20—C25—C24	121.4 (3)
O4—C9—H9	107.7	C20—C25—H25	119.3
C8—C9—H9	107.7	C24—C25—H25	119.3
C10—C9—H9	107.7	C4—C26—H26A	109.5
C9—C10—C11	114.6 (2)	C4—C26—H26B	109.5
C9—C10—H10A	108.6	H26A—C26—H26B	109.5
C11—C10—H10A	108.6	C4—C26—H26C	109.5
C9—C10—H10B	108.6	H26A—C26—H26C	109.5
C11—C10—H10B	108.6	H26B—C26—H26C	109.5
H10A—C10—H10B	107.6	C8—C27—H27A	109.5
C12—C11—C1	103.3 (2)	C8—C27—H27B	109.5
C12—C11—C10	114.3 (2)	H27A—C27—H27B	109.5
C1—C11—C10	116.4 (2)	C8—C27—H27C	109.5
C12—C11—H11	107.5	H27A—C27—H27C	109.5
C1—C11—H11	107.5	H27B—C27—H27C	109.5
C10—C11—H11	107.5	O5—C28—H28A	109.5
C13—C12—C15	109.7 (2)	O5—C28—H28B	109.5
C13—C12—C11	104.7 (2)	H28A—C28—H28B	109.5
C15—C12—C11	114.2 (2)	O5—C28—H28C	109.5
C13—C12—H12	109.4	H28A—C28—H28C	109.5
C15—C12—H12	109.4	H28B—C28—H28C	109.5
C11—C12—H12	109.4	C16—N1—C15	111.1 (2)
O12—C13—O14	120.4 (2)	C16—N1—C19	107.7 (2)
O12—C13—C12	129.1 (2)	C15—N1—C19	109.4 (2)
O14—C13—C12	110.5 (2)	C20—N2—C17	116.3 (2)
N1—C15—C12	113.2 (2)	C20—N2—C18	117.5 (2)
N1—C15—H15A	108.9	C17—N2—C18	110.9 (2)
C12—C15—H15A	108.9	C4—O3—C2	60.88 (17)
N1—C15—H15B	108.9	C9—O4—H4	109.5
C12—C15—H15B	108.9	C23—O5—C28	117.9 (3)
H15A—C15—H15B	107.8	C13—O14—C1	111.0 (2)
N1—C16—C17	111.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···N1	0.84	2.14	2.977 (4)	170
C2—H2···O12ⁱ	1.00	2.42	3.225 (4)	137
C5—H5B···O3ⁱⁱ	0.99	2.45	3.310 (4)	145
C7—H7···O14ⁱⁱⁱ	0.95	2.50	3.198 (4)	130
C15—H15A···O12ⁱ	0.99	2.57	3.413 (4)	143
C15—H15A···O14ⁱ	0.99	2.50	3.469 (4)	165

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

Experimental details

Crystal data
Chemical formula	C₂₆H₃₆N₂O₅
M_r	456.57
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	180
a, b, c (Å)	6.7066 (7), 11.9033 (11), 30.322 (4)
V (Å³)	2420.6 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.33 × 0.17 × 0.04

Data collection
Diffractometer	Agilent Xcalibur Sapphire1 (long nozzle) diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.732, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	14543, 4925, 3663
R_int	0.055
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.130, 1.04
No. of reflections	4925
No. of parameters	303
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.23

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
O4—H4···N1	0.84	2.14	2.977 (4)	170
C2—H2···O12ⁱ	1.00	2.42	3.225 (4)	137
C5—H5B···O3ⁱⁱ	0.99	2.45	3.310 (4)	145
C7—H7···O14ⁱⁱⁱ	0.95	2.50	3.198 (4)	130
C15—H15A···O12ⁱ	0.99	2.57	3.413 (4)	143
C15—H15A···O14ⁱ	0.99	2.50	3.469 (4)	165

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

Acknowledgements

The authors thank Professor El Ammari for discussions on the refinement of the structure.

References

Abdel Sattar, E., Galal, A. M. & Mossa, J. S. (1996). J. Nat. Prod. 59, 403–405. CrossRef CAS PubMed Google Scholar
Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England. Google Scholar
Bellakhdar, J. (1997). La Pharmacopée Marocaine Traditionnelle, pp. 272–274. Paris: Ibis Press. 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
Qureshi, S., Ageel, A. M., Al-Yahya, M. A., Tariq, M., Mossa, J. S. & Shah, A. H. (1990). J. Ethnopharmacol. 28, 157-162. CrossRef CAS PubMed Web of Science 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

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Volume 68| Part 3| March 2012| Pages o589-o590

doi:10.1107/S1600536812003662

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

9α-Hy­dr­oxy-12-{[4-(4-meth­­oxy­phen­yl)piperazin-1-yl]meth­yl}-4,8-di­methyl-3,14-dioxatri­cyclo­[9.3.0.02,4]tetra­dec-7-en-13-one

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

9α-Hydroxy-12-{[4-(4-methoxyphenyl)piperazin-1-yl]methyl}-4,8-dimethyl-3,14-dioxatricyclo[9.3.0.0^2,4]tetradec-7-en-13-one