1-(3-p-Tolyl­isoxazol-5-yl)cyclo­hexa­nol

Khalil, O.; Bougrin, K.; Benhida, R.; Soufiaoui, M.; Ammari, L.E.

doi:10.1107/S1600536809044900

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o2971

doi:10.1107/S1600536809044900

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1-(3-p-Tolylisoxazol-5-yl)cyclohexanol

Ouafaa Khalil,^a Khalid Bougrin,^a Rachid Benhida,^b Mohamed Soufiaoui ^a and Lahcen El Ammari ^c ^*

^aLaboratoire de Chimie des Plantes et de Synthèse Organique et Bioorganique, Département de Chimie, Faculté des Sciences BP, 1014 Rabat, Morocco, ^bLaboratoire de Chimie des Molécules Bioactives et des Arômes, UMR-CNRS 6001, Institut de Chimie de Nice, Université de Nice-Sophia Antipolis, Parc Valrose, F-06108 Nice Cédex 2, France, and ^cLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, 4, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
^*Correspondence e-mail: l_elammari@fsr.ac.ma

(Received 20 October 2009; accepted 27 October 2009; online 4 November 2009)

The title compound, C₁₆H₁₉NO₂, contains two molecules in the asymmetric unit. Each molecule is composed of three interconnected rings, two essentially planar rings, viz. the isoxazole and the methylbenzyl aromatic ring [maximum deviations of 0.0027 (13) and 0.0031 (19) Å from the isoxazole and methylbenzyl ring planes, respectively, in the first molecule, 0.0018 (12) and 0.019 (2) Å in the second molecule], and one cyclohexanol ring having a chair conformation. Although the two molecules have similar bond distances and angles, they differ in the orientation of the cyclohexanol ring with respect to the tolylisoxazole unit. In the first molecule, the dihedral angle between the isoxazole and methylbenzyl rings is 22.03 (8)° and between the isoxazole and cyclohexanol rings is 30.15 (8)°. The corresponding values in the second molecule are 6.13 (10) and 88.44 (8)°, respectively. In the crystal, the molecules are linked by O—H⋯O and O—H⋯N hydrogen bonds, building up a zigzag chain parallel to the a axis.

Related literature

For isoxazole derivatives as building blocks in organic synthesis and combinatorial chemistry, see: Tu et al. (2009 ); Tang et al. (2009 ). For their biological activity, see: Deng et al. (2009 ); Kozikowski et al. (2008 ); Lee et al. (2009 ).

Experimental

Crystal data

C₁₆H₁₉NO₂
M_r = 257.32
Orthorhombic, P c a 2₁
a = 10.9404 (3) Å
b = 9.7136 (3) Å
c = 26.9207 (7) Å
V = 2860.88 (14) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 K
0.18 × 0.17 × 0.10 mm

Data collection

Bruker X8 APEXII diffractometer
Absorption correction: none
87116 measured reflections
4377 independent reflections
3820 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.105
S = 1.04
4377 reflections
347 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.20 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
O1—H1⋯O2	0.82	1.98	2.7892 (12)	168
O2—H2⋯N2ⁱ	0.82	2.05	2.8629 (16)	173
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+1, z]$ .

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/S1600536809044900/dn2504sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809044900/dn2504Isup2.hkl

checkCIF report

Comment top

Isoxazole derivatives are important class of heterocyclic compounds and their chemical and biochemical properties have been extensively studied. They have served as a versatile building blocks in organic synthesis and combinatorial chemistry (Tu et al. 2009, Tang et al. 2009). Isoxazole systems have also been targeted in synthetic investigations for their known biological and pharmacological properties such as hypoglycemic, anti-inflammatory and anti-bacterial activities. Recently, the growing interest in such analogues also rises from their high potential value as antiviral (Deng et al. 2009, Lee et al. 2009) and anti-tumor agents (Kozikowski et al. 2008).

We have undertaken the X-ray diffraction study of the title compound, in order to understand the molecular features which stabilize its observed conformation. The asymmetric unit contains two molecules crystallographically independent. Each molecule is formed by three interconnected cycles, two essentially planar rings: isoxazole and methylbenzyl rings while the 3rd ring (cyclohexanol) has a chair conformation (Fig. 1). The difference between the molecules lies in the orientation of the rings in each molecule as shown in the fitting drawing (Fig. 2) obtained with PLATON (Spek, 2003). Thus in the first molecule (C1 to C15) the dihedral angles between the isoxazole ring and methylbenzyl ring planes is 22.03 (8)° and between the isoxazole and cyclohexanol ring planes is 30.15 (8)°. Whereas in the second molecule (C16 to C30), equivalent angles have as values 6.13 (10) and 88.44 (8)°, respectively.

The two molecules within the asymmetric unit are linked through O-H···O hydrogen bond building a pseudo dimer. These pseudo dimers are further linked to each other by O-H···N hydrogen bonds forming a zig-zag like chain parallel to the a axis (Table 1, Fig. 3).

Related literature top

For isoxazole derivatives as building blocks in organic synthesis and combinatorial chemistry, see: Tu et al. (2009); Tang et al. (2009). For their biological activity, see: Deng et al. (2009); Kozikowski et al. (2008); Lee et al. (2009).

Experimental top

A mixture of 1-ethynylcyclohexanol (1 mmol) and p-methylbenzylaldoxime (1.2 mmol) was dissolved in CH₂Cl₂ (20 ml), the solution was then cooled thoroughly with ice at 0–5°C. 15 ml of sodium hydroxide solution (12 g. of sodium hydroxide per 100 g. of water) were gradually added under vigorously stirring for 5 h. The organic phase was separated and dried over anhydrous sodium sulfate, filtered and the solvent evaporated under reduced pressure. The residue was purified by recrystallization from ethanol. The structure of adduct was confirmed by spectroscopic methods.

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 view of the asymmetric unit with the atom labeling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii. Hydrogen bond is shown as dashed line.
	Fig. 2. : View showing the fitting of the two molecules building the asymmetric unit.
	Fig. 3. : Partial packing view showing the formation of a chain through O—H···N hydrogen bonds shown as dashed lines. H atoms not involved in hydrogen bondings have been omitted for clarity. [Symmetry code: (i) -x-1/2, y+1, z+1/2]

1-(3-p-Tolylisoxazol-5-yl)cyclohexanol top

Crystal data top

C₁₆H₁₉NO₂	F(000) = 1104
M_r = 257.32	D_x = 1.195 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 4377 reflections
a = 10.9404 (3) Å	θ = 2.6–30.3°
b = 9.7136 (3) Å	µ = 0.08 mm⁻¹
c = 26.9207 (7) Å	T = 298 K
V = 2860.88 (14) Å³	Bloc, colourless
Z = 8	0.18 × 0.17 × 0.10 mm

Data collection top

Bruker X8 APEXII diffractometer	3820 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.032
Graphite monochromator	θ_max = 30.3°, θ_min = 0.8°
ϕ and ω scans	h = −15→15
87116 measured reflections	k = −13→13
4377 independent reflections	l = −38→38

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.105	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0535P)² + 0.2498P] where P = (F_o² + 2F_c²)/3
8578 reflections	(Δ/σ)_max = 0.008
347 parameters	Δρ_max = 0.20 e Å⁻³
1 restraint	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₁₆H₁₉NO₂	V = 2860.88 (14) Å³
M_r = 257.32	Z = 8
Orthorhombic, Pca2₁	Mo Kα radiation
a = 10.9404 (3) Å	µ = 0.08 mm⁻¹
b = 9.7136 (3) Å	T = 298 K
c = 26.9207 (7) Å	0.18 × 0.17 × 0.10 mm

Data collection top

Bruker X8 APEXII diffractometer	3820 reflections with I > 2σ(I)
87116 measured reflections	R_int = 0.032
4377 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	1 restraint
wR(F²) = 0.105	H-atom parameters constrained
S = 1.04	Δρ_max = 0.20 e Å⁻³
8578 reflections	Δρ_min = −0.15 e Å⁻³
347 parameters

Special details top

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 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 > σ(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
O1	0.06445 (8)	0.00823 (10)	0.57893 (4)	0.0480 (2)
H1	0.0930	0.0832	0.5867	0.072*
O3	0.11978 (9)	−0.17692 (11)	0.65818 (4)	0.0483 (2)
N1	0.17299 (11)	−0.19192 (14)	0.70537 (4)	0.0503 (3)
C1	0.26673 (12)	−0.03462 (16)	0.54425 (5)	0.0477 (3)
H1A	0.3325	−0.1015	0.5438	0.057*
H1B	0.2974	0.0489	0.5595	0.057*
C2	0.22715 (16)	−0.0037 (2)	0.49105 (6)	0.0619 (4)
H2A	0.1661	0.0688	0.4913	0.074*
H2B	0.2970	0.0287	0.4722	0.074*
C3	0.17463 (17)	−0.1307 (2)	0.46633 (6)	0.0656 (4)
H3A	0.2377	−0.2004	0.4634	0.079*
H3B	0.1468	−0.1075	0.4332	0.079*
C4	0.06776 (16)	−0.18753 (18)	0.49661 (6)	0.0584 (4)
H4A	0.0014	−0.1214	0.4964	0.070*
H4B	0.0384	−0.2717	0.4813	0.070*
C5	0.10482 (13)	−0.21730 (13)	0.55016 (6)	0.0475 (3)
H5A	0.1636	−0.2921	0.5507	0.057*
H5B	0.0335	−0.2463	0.5688	0.057*
C6	0.16095 (10)	−0.09053 (12)	0.57496 (5)	0.0365 (2)
C7	0.20414 (11)	−0.12361 (12)	0.62677 (5)	0.0384 (2)
C8	0.31007 (12)	−0.10441 (14)	0.65116 (5)	0.0420 (3)
H8	0.3830	−0.0699	0.6385	0.050*
C9	0.28579 (12)	−0.14860 (13)	0.70052 (5)	0.0406 (3)
C10	0.36790 (13)	−0.14279 (14)	0.74392 (5)	0.0440 (3)
C11	0.46620 (14)	−0.05373 (16)	0.74405 (5)	0.0512 (3)
H11	0.4817	0.0003	0.7162	0.061*
C12	0.54184 (16)	−0.04399 (19)	0.78505 (6)	0.0587 (4)
H12	0.6074	0.0169	0.7844	0.070*
C13	0.52180 (16)	−0.12314 (19)	0.82699 (6)	0.0603 (4)
C14	0.42354 (18)	−0.2130 (2)	0.82669 (6)	0.0653 (4)
H14	0.4087	−0.2677	0.8544	0.078*
C15	0.34695 (16)	−0.22311 (18)	0.78595 (6)	0.0577 (4)
H15	0.2812	−0.2838	0.7866	0.069*
C31	0.6071 (2)	−0.1127 (3)	0.87111 (8)	0.0909 (7)
H31A	0.6901	−0.1222	0.8601	0.136*
H31B	0.5885	−0.1845	0.8944	0.136*
H31C	0.5968	−0.0247	0.8868	0.136*
O2	0.13845 (8)	0.27957 (9)	0.59456 (4)	0.0446 (2)
H2	0.0833	0.3217	0.5806	0.067*
O4	0.37614 (10)	0.53575 (12)	0.59082 (4)	0.0551 (3)
N2	0.43241 (12)	0.59158 (15)	0.54833 (5)	0.0567 (3)
C16	0.30531 (13)	0.29329 (15)	0.65160 (6)	0.0474 (3)
H16A	0.3400	0.2165	0.6334	0.057*
H16B	0.3721	0.3518	0.6624	0.057*
C17	0.23731 (17)	0.23905 (17)	0.69701 (6)	0.0587 (4)
H17A	0.1780	0.1707	0.6865	0.070*
H17B	0.2949	0.1944	0.7192	0.070*
C18	0.1719 (2)	0.35391 (19)	0.72487 (6)	0.0650 (4)
H18A	0.1269	0.3153	0.7526	0.078*
H18B	0.2316	0.4182	0.7380	0.078*
C19	0.08429 (16)	0.42955 (17)	0.69051 (6)	0.0570 (4)
H19A	0.0211	0.3668	0.6793	0.068*
H19B	0.0453	0.5041	0.7085	0.068*
C20	0.15192 (13)	0.48696 (13)	0.64607 (5)	0.0439 (3)
H20A	0.2097	0.5561	0.6573	0.053*
H20B	0.0939	0.5316	0.6241	0.053*
C21	0.22078 (11)	0.37544 (12)	0.61712 (5)	0.0383 (2)
C22	0.29290 (11)	0.44198 (13)	0.57612 (5)	0.0398 (2)
C23	0.29195 (13)	0.43498 (14)	0.52616 (5)	0.0459 (3)
H23	0.2431	0.3792	0.5063	0.055*
C24	0.38164 (12)	0.53111 (14)	0.51042 (5)	0.0437 (3)
C25	0.41837 (14)	0.56858 (16)	0.45954 (6)	0.0507 (3)
C26	0.49890 (17)	0.6774 (2)	0.45147 (7)	0.0678 (4)
H26	0.5283	0.7284	0.4781	0.081*
C27	0.53507 (19)	0.7092 (3)	0.40341 (8)	0.0829 (6)
H27	0.5887	0.7822	0.3984	0.099*
C28	0.4935 (2)	0.6354 (2)	0.36267 (7)	0.0763 (5)
C29	0.4112 (3)	0.5332 (3)	0.37146 (8)	0.0963 (8)
H29	0.3792	0.4847	0.3446	0.116*
C30	0.3732 (3)	0.4987 (2)	0.41912 (7)	0.0801 (6)
H34	0.3170	0.4280	0.4237	0.096*
C32	0.5363 (3)	0.6679 (4)	0.31036 (9)	0.1103 (9)
H32A	0.5810	0.7529	0.3105	0.165*
H32B	0.4668	0.6761	0.2888	0.165*
H32C	0.5883	0.5951	0.2987	0.165*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0360 (4)	0.0406 (4)	0.0675 (6)	0.0067 (3)	−0.0034 (4)	−0.0048 (4)
O3	0.0416 (5)	0.0563 (5)	0.0471 (5)	−0.0072 (4)	0.0036 (4)	−0.0019 (4)
N1	0.0518 (7)	0.0578 (7)	0.0413 (6)	−0.0064 (5)	0.0042 (5)	0.0006 (5)
C1	0.0346 (6)	0.0643 (8)	0.0443 (7)	−0.0050 (5)	−0.0031 (5)	0.0053 (6)
C2	0.0513 (8)	0.0882 (11)	0.0463 (7)	−0.0129 (8)	−0.0041 (6)	0.0164 (8)
C3	0.0653 (10)	0.0874 (12)	0.0440 (7)	0.0045 (9)	−0.0063 (7)	−0.0033 (8)
C4	0.0627 (9)	0.0580 (8)	0.0546 (8)	−0.0075 (7)	−0.0155 (7)	−0.0070 (7)
C5	0.0533 (7)	0.0382 (6)	0.0510 (7)	−0.0019 (5)	−0.0065 (6)	−0.0037 (6)
C6	0.0306 (5)	0.0353 (5)	0.0436 (6)	0.0027 (4)	−0.0025 (4)	−0.0008 (4)
C7	0.0355 (6)	0.0366 (5)	0.0432 (6)	0.0025 (4)	0.0045 (4)	−0.0038 (5)
C8	0.0369 (6)	0.0478 (6)	0.0413 (6)	0.0019 (5)	0.0017 (5)	0.0031 (5)
C9	0.0441 (6)	0.0372 (6)	0.0404 (6)	0.0040 (5)	0.0039 (5)	−0.0018 (5)
C10	0.0487 (7)	0.0457 (6)	0.0376 (6)	0.0065 (5)	0.0020 (5)	−0.0009 (5)
C11	0.0560 (8)	0.0534 (7)	0.0442 (7)	−0.0014 (6)	−0.0032 (6)	0.0061 (6)
C12	0.0553 (9)	0.0671 (9)	0.0538 (8)	−0.0039 (7)	−0.0081 (6)	0.0015 (7)
C13	0.0632 (9)	0.0777 (11)	0.0400 (7)	0.0091 (8)	−0.0050 (6)	−0.0035 (7)
C14	0.0756 (11)	0.0816 (12)	0.0387 (7)	−0.0003 (9)	0.0005 (7)	0.0116 (7)
C15	0.0626 (9)	0.0641 (9)	0.0465 (7)	−0.0053 (7)	0.0029 (6)	0.0076 (7)
C31	0.0888 (15)	0.132 (2)	0.0516 (10)	−0.0045 (14)	−0.0215 (10)	0.0034 (12)
O2	0.0412 (5)	0.0333 (4)	0.0595 (6)	−0.0003 (3)	−0.0095 (4)	−0.0018 (4)
O4	0.0527 (6)	0.0675 (7)	0.0449 (5)	−0.0229 (5)	−0.0046 (4)	0.0012 (5)
N2	0.0524 (7)	0.0693 (8)	0.0483 (6)	−0.0200 (6)	−0.0015 (5)	0.0057 (6)
C16	0.0452 (7)	0.0445 (6)	0.0523 (7)	0.0060 (5)	−0.0096 (5)	0.0034 (6)
C17	0.0703 (10)	0.0523 (8)	0.0535 (8)	0.0080 (7)	−0.0056 (7)	0.0127 (6)
C18	0.0870 (12)	0.0643 (10)	0.0439 (7)	0.0032 (9)	0.0041 (7)	0.0064 (7)
C19	0.0615 (9)	0.0545 (8)	0.0550 (8)	0.0079 (7)	0.0128 (7)	0.0000 (6)
C20	0.0471 (7)	0.0360 (6)	0.0486 (7)	0.0035 (5)	0.0000 (5)	−0.0009 (5)
C21	0.0363 (6)	0.0338 (5)	0.0446 (6)	0.0007 (4)	−0.0034 (5)	0.0002 (5)
C22	0.0361 (6)	0.0371 (5)	0.0461 (6)	0.0018 (4)	−0.0040 (5)	−0.0010 (5)
C23	0.0481 (7)	0.0426 (6)	0.0470 (7)	−0.0042 (5)	−0.0044 (5)	−0.0050 (5)
C24	0.0403 (6)	0.0431 (6)	0.0476 (7)	0.0030 (5)	0.0005 (5)	−0.0008 (5)
C25	0.0502 (7)	0.0519 (7)	0.0501 (7)	0.0068 (6)	0.0036 (6)	0.0036 (6)
C26	0.0579 (9)	0.0868 (12)	0.0586 (9)	−0.0137 (8)	0.0026 (7)	0.0075 (8)
C27	0.0667 (11)	0.1048 (16)	0.0772 (14)	−0.0099 (10)	0.0099 (10)	0.0285 (12)
C28	0.0845 (13)	0.0901 (14)	0.0544 (9)	0.0206 (11)	0.0148 (9)	0.0135 (10)
C29	0.149 (2)	0.0882 (16)	0.0514 (10)	−0.0098 (16)	0.0070 (13)	−0.0056 (10)
C30	0.1169 (17)	0.0688 (11)	0.0545 (9)	−0.0194 (11)	0.0065 (10)	−0.0061 (9)
C32	0.126 (2)	0.141 (2)	0.0640 (13)	0.0189 (19)	0.0251 (13)	0.0296 (14)

Geometric parameters (Å, º) top

O1—C6	1.4305 (14)	O2—C21	1.4308 (15)
O1—H1	0.8200	O2—H2	0.8200
O3—C7	1.3546 (15)	O4—C22	1.3473 (16)
O3—N1	1.4051 (16)	O4—N2	1.4076 (17)
N1—C9	1.3103 (18)	N2—C24	1.3021 (19)
C1—C6	1.5223 (18)	C16—C17	1.525 (2)
C1—C2	1.526 (2)	C16—C21	1.5342 (17)
C1—H1A	0.9700	C16—H16A	0.9700
C1—H1B	0.9700	C16—H16B	0.9700
C2—C3	1.515 (3)	C17—C18	1.523 (2)
C2—H2A	0.9700	C17—H17A	0.9700
C2—H2B	0.9700	C17—H17B	0.9700
C3—C4	1.528 (3)	C18—C19	1.521 (3)
C3—H3A	0.9700	C18—H18A	0.9700
C3—H3B	0.9700	C18—H18B	0.9700
C4—C5	1.525 (2)	C19—C20	1.513 (2)
C4—H4A	0.9700	C19—H19A	0.9700
C4—H4B	0.9700	C19—H19B	0.9700
C5—C6	1.5294 (17)	C20—C21	1.5325 (18)
C5—H5A	0.9700	C20—H20A	0.9700
C5—H5B	0.9700	C20—H20B	0.9700
C6—C7	1.5072 (17)	C21—C22	1.5027 (18)
C7—C8	1.3450 (18)	C22—C23	1.3469 (19)
C8—C9	1.4215 (17)	C23—C24	1.419 (2)
C8—H8	0.9300	C23—H23	0.9300
C9—C10	1.4747 (19)	C24—C25	1.473 (2)
C10—C11	1.380 (2)	C25—C30	1.375 (3)
C10—C15	1.393 (2)	C25—C26	1.393 (2)
C11—C12	1.383 (2)	C26—C27	1.388 (3)
C11—H11	0.9300	C26—H26	0.9300
C12—C13	1.384 (2)	C27—C28	1.387 (3)
C12—H12	0.9300	C27—H27	0.9300
C13—C14	1.385 (3)	C28—C29	1.362 (4)
C13—C31	1.514 (2)	C28—C32	1.517 (3)
C14—C15	1.384 (2)	C29—C30	1.390 (3)
C14—H14	0.9300	C29—H29	0.9300
C15—H15	0.9300	C30—H34	0.9300
C31—H31A	0.9600	C32—H32A	0.9600
C31—H31B	0.9600	C32—H32B	0.9600
C31—H31C	0.9600	C32—H32C	0.9600

C6—O1—H1	109.5	C21—O2—H2	109.5
C7—O3—N1	108.77 (10)	C22—O4—N2	108.51 (11)
C9—N1—O3	105.48 (10)	C24—N2—O4	106.05 (11)
C6—C1—C2	111.35 (11)	C17—C16—C21	111.76 (12)
C6—C1—H1A	109.4	C17—C16—H16A	109.3
C2—C1—H1A	109.4	C21—C16—H16A	109.3
C6—C1—H1B	109.4	C17—C16—H16B	109.3
C2—C1—H1B	109.4	C21—C16—H16B	109.3
H1A—C1—H1B	108.0	H16A—C16—H16B	107.9
C3—C2—C1	111.08 (14)	C18—C17—C16	111.78 (13)
C3—C2—H2A	109.4	C18—C17—H17A	109.3
C1—C2—H2A	109.4	C16—C17—H17A	109.3
C3—C2—H2B	109.4	C18—C17—H17B	109.3
C1—C2—H2B	109.4	C16—C17—H17B	109.3
H2A—C2—H2B	108.0	H17A—C17—H17B	107.9
C2—C3—C4	110.49 (14)	C19—C18—C17	110.50 (14)
C2—C3—H3A	109.6	C19—C18—H18A	109.5
C4—C3—H3A	109.6	C17—C18—H18A	109.5
C2—C3—H3B	109.6	C19—C18—H18B	109.5
C4—C3—H3B	109.6	C17—C18—H18B	109.5
H3A—C3—H3B	108.1	H18A—C18—H18B	108.1
C5—C4—C3	111.66 (13)	C20—C19—C18	110.53 (14)
C5—C4—H4A	109.3	C20—C19—H19A	109.5
C3—C4—H4A	109.3	C18—C19—H19A	109.5
C5—C4—H4B	109.3	C20—C19—H19B	109.5
C3—C4—H4B	109.3	C18—C19—H19B	109.5
H4A—C4—H4B	107.9	H19A—C19—H19B	108.1
C4—C5—C6	111.51 (12)	C19—C20—C21	112.46 (11)
C4—C5—H5A	109.3	C19—C20—H20A	109.1
C6—C5—H5A	109.3	C21—C20—H20A	109.1
C4—C5—H5B	109.3	C19—C20—H20B	109.1
C6—C5—H5B	109.3	C21—C20—H20B	109.1
H5A—C5—H5B	108.0	H20A—C20—H20B	107.8
O1—C6—C7	107.77 (10)	O2—C21—C22	107.39 (10)
O1—C6—C1	111.25 (10)	O2—C21—C20	111.49 (10)
C7—C6—C1	109.89 (10)	C22—C21—C20	109.12 (10)
O1—C6—C5	106.03 (10)	O2—C21—C16	107.32 (10)
C7—C6—C5	110.98 (10)	C22—C21—C16	110.59 (10)
C1—C6—C5	110.82 (11)	C20—C21—C16	110.87 (11)
C8—C7—O3	109.59 (11)	C23—C22—O4	109.43 (12)
C8—C7—C6	133.82 (11)	C23—C22—C21	135.04 (12)
O3—C7—C6	116.46 (10)	O4—C22—C21	115.47 (11)
C7—C8—C9	104.69 (11)	C22—C23—C24	105.05 (12)
C7—C8—H8	127.7	C22—C23—H23	127.5
C9—C8—H8	127.7	C24—C23—H23	127.5
N1—C9—C8	111.47 (12)	N2—C24—C23	110.96 (13)
N1—C9—C10	120.48 (12)	N2—C24—C25	120.07 (13)
C8—C9—C10	127.96 (12)	C23—C24—C25	128.96 (13)
C11—C10—C15	118.49 (13)	C30—C25—C26	118.61 (16)
C11—C10—C9	120.05 (12)	C30—C25—C24	121.05 (15)
C15—C10—C9	121.44 (13)	C26—C25—C24	120.34 (15)
C10—C11—C12	120.75 (14)	C27—C26—C25	119.66 (19)
C10—C11—H11	119.6	C27—C26—H26	120.2
C12—C11—H11	119.6	C25—C26—H26	120.2
C11—C12—C13	121.24 (16)	C28—C27—C26	121.9 (2)
C11—C12—H12	119.4	C28—C27—H27	119.0
C13—C12—H12	119.4	C26—C27—H27	119.0
C12—C13—C14	117.94 (14)	C29—C28—C27	117.17 (18)
C12—C13—C31	120.35 (18)	C29—C28—C32	121.1 (2)
C14—C13—C31	121.69 (17)	C27—C28—C32	121.7 (2)
C15—C14—C13	121.28 (15)	C28—C29—C30	122.3 (2)
C15—C14—H14	119.4	C28—C29—H29	118.9
C13—C14—H14	119.4	C30—C29—H29	118.9
C14—C15—C10	120.30 (16)	C25—C30—C29	120.3 (2)
C14—C15—H15	119.9	C25—C30—H34	119.9
C10—C15—H15	119.9	C29—C30—H34	119.9
C13—C31—H31A	109.5	C28—C32—H32A	109.5
C13—C31—H31B	109.5	C28—C32—H32B	109.5
H31A—C31—H31B	109.5	H32A—C32—H32B	109.5
C13—C31—H31C	109.5	C28—C32—H32C	109.5
H31A—C31—H31C	109.5	H32A—C32—H32C	109.5
H31B—C31—H31C	109.5	H32B—C32—H32C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.82	1.98	2.7892 (12)	168
O2—H2···N2ⁱ	0.82	2.05	2.8629 (16)	173

Symmetry code: (i) x−1/2, −y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₉NO₂
M_r	257.32
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	298
a, b, c (Å)	10.9404 (3), 9.7136 (3), 26.9207 (7)
V (Å³)	2860.88 (14)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.18 × 0.17 × 0.10

Data collection
Diffractometer	Bruker X8 APEXII diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	87116, 4377, 3820
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.710

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.105, 1.04
No. of reflections	8578
No. of parameters	347
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.15

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
O1—H1···O2	0.82	1.98	2.7892 (12)	167.8
O2—H2···N2ⁱ	0.82	2.05	2.8629 (16)	173.3

Symmetry code: (i) x−1/2, −y+1, z.

Acknowledgements

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for making this work possible. They also thank H. Zouihri for his helpful technical assistance during the X-ray measurements.

References

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